5-Diethyl­amino-2-[(E)-(4-methyl-3-nitro­phenyl)­imino­meth­yl]phenol: a redetermination (2024)

5-Diethyl­amino-2-[(E)-(4-methyl-3-nitro­phenyl)­imino­meth­yl]phenol: a redetermination (1)organic compounds

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Acta Cryst. (2009). E65, o349-o350
https://doi.org/10.1107/S1600536809001731

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5-Diethyl­amino-2-[(E)-(4-methyl-3-nitro­phenyl)­imino­meth­yl]phenol: a redetermination (26)

H.-K. Fun, R. Kia, A. M. Vijesh and A. M. Isloor

The title compound, C18H21N3O3, is a potential bidentate Schiff base ligand. The whole mol­ecule is disordered with a refined site-occupancy ratio of 0.567 (4):0.433 (4) and not just one ethyl group as reported previously [Sarojini et al. (2007). Acta Cryst. E63, o4782–o4782]. Using the whole mol­ecule disorder, R values are much smaller than those published. An intra­molecular O—H5-Diethyl­amino-2-[(E)-(4-methyl-3-nitro­phenyl)­imino­meth­yl]phenol: a redetermination (27)N hydrogen bond generates a six-membered ring, producing an S(6) ring motif. The dihedral angle between the mean plane of the two benzene rings (major component) is 9.0 (5)°. The crystal structure shows short C5-Diethyl­amino-2-[(E)-(4-methyl-3-nitro­phenyl)­imino­meth­yl]phenol: a redetermination (28)C [3.189 (15)–3.298 (12) Å] and C5-Diethyl­amino-2-[(E)-(4-methyl-3-nitro­phenyl)­imino­meth­yl]phenol: a redetermination (29)O [2.983 (5)–3.149 (13) Å] contacts. Inter­molecular C—H5-Diethyl­amino-2-[(E)-(4-methyl-3-nitro­phenyl)­imino­meth­yl]phenol: a redetermination (30)O inter­actions link neighbouring mol­ecules into dimers with R22(18) motifs. In the crystal structure, these dimers are linked together by inter­molecular C—H5-Diethyl­amino-2-[(E)-(4-methyl-3-nitro­phenyl)­imino­meth­yl]phenol: a redetermination (31)O inter­actions into one-dimensional extended chains along the b axis. The crystal structure is further stabilized by inter­molecular π–π stacking inter­actions [centroid–centroid distances = 3.458 (8)–3.691 (6) Å].

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Supporting information

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536809001731/at2709sup1.cif
Contains datablocks global, I

Structure factor file (CIF format) https://doi.org/10.1107/S1600536809001731/at2709Isup2.hkl
Contains datablock I

CCDC reference: 722081

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean 5-Diethyl­amino-2-[(E)-(4-methyl-3-nitro­phenyl)­imino­meth­yl]phenol: a redetermination (36)() = 0.000 Å
  • Disorder in main residue
  • R factor = 0.043
  • wR factor = 0.117
  • Data-to-parameter ratio = 11.5

checkCIF/PLATON results

No syntax errors found5-Diethyl­amino-2-[(E)-(4-methyl-3-nitro­phenyl)­imino­meth­yl]phenol: a redetermination (37)Alert level BPLAT301_ALERT_3_B Main Residue Disorder ......................... 50.00 Perc.5-Diethyl­amino-2-[(E)-(4-methyl-3-nitro­phenyl)­imino­meth­yl]phenol: a redetermination (38)Alert level CPLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.76 RatioPLAT220_ALERT_2_C Large Non-Solvent N Ueq(max)/Ueq(min) ... 2.54 RatioPLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 2.96 RatioPLAT230_ALERT_2_C Hirshfeld Test Diff for N2A -- C14A .. 5.34 suPLAT230_ALERT_2_C Hirshfeld Test Diff for C1A -- C6A .. 5.68 suPLAT230_ALERT_2_C Hirshfeld Test Diff for C6A -- C7A .. 5.15 suPLAT230_ALERT_2_C Hirshfeld Test Diff for C8A -- C13A .. 5.70 suPLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N3APLAT432_ALERT_2_C Short Inter X...Y Contact O3A .. C15A .. 2.98 Ang.PLAT432_ALERT_2_C Short Inter X...Y Contact C3B .. C12B .. 3.19 Ang.PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?PLAT234_ALERT_4_C Large Hirshfeld Difference C5A -- C6A .. 0.10 Ang.PLAT234_ALERT_4_C Large Hirshfeld Difference C8A -- C9A .. 0.12 Ang.PLAT234_ALERT_4_C Large Hirshfeld Difference C9A -- C10A .. 0.11 Ang.PLAT234_ALERT_4_C Large Hirshfeld Difference C10A -- C11A .. 0.11 Ang.PLAT234_ALERT_4_C Large Hirshfeld Difference C11A -- C12A .. 0.11 Ang.PLAT234_ALERT_4_C Large Hirshfeld Difference C12A -- C13A .. 0.11 Ang.5-Diethyl­amino-2-[(E)-(4-methyl-3-nitro­phenyl)­imino­meth­yl]phenol: a redetermination (39)Alert level GPLAT333_ALERT_2_G Check Large Av C6-Ring C-C Dist. C1A -C6A 1.41 Ang.PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1197PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels .......... 10 0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 17 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 11 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 7 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

Compounds with the structure of –CN– (azomethine group) are known asSchiff bases, which are usually synthesized by the condensation of primaryamines and active carbonyl groups. The chemistry of the carbon-nitrogen doublebond plays a vital role in the progresses of chemistry (Patai 1970).They havebeen used as intermediates in medical substrates and as ligands in complexformation with some metal ions (Tai et al., 2003). Recentlymulti-dentate complexes of iron and nickel showed high activities of ethyleneoligomerization and polymerization (Ittel et al., 2000). Theyhaveshown biological activities including antibacterial (Kabeer et al.,2001; Pandeya et al., 1999), antifungal (More etal., 2001;Singh & Dash 1988), anticancer (Isloor et al., 2009;Pathak etal., 2000), anti-inflammatory (Vazzanaa et al.,2004) andherbicidal (Samadhiya & Halve 2001) activities. In addition, Schiffbases havealso been used as starting materials in the synthesis of large bioactive andindustrial compounds via ring closure, cycloaddition and replacement reactions(Aydoğan et al., 2001).

In the title compound, (I), (Fig. 1), an intramolecular O—H···N hydrogen bondgenerate a six-membered ring, producing S(6) ring motif (Table 1).Intermolecular C—H···O interactions link neighbouring molecules into dimerswith R22(18) motifs (Table 1, Fig. 2). The whole molecule isdisordered with a site occupancy ratio of 0.567(4)/0.433(4) and not just theethyl group as mentioned in the previously reported article (Sarojini etal., 2007). Using the whole molecule disorder, R-values are muchsmallerthan those published.

The two substituted benzene rings are not coplanar and make a dihedral angle of9.0(5)° (for major component A). The interesting features of the crystalstructure is short C1A···C8Ai [3.298(12) Å;(i) 1-x,-y,2-z], C1B···C8Bi[3.329(16) Å], C3B···C12Bi [3.189(15) Å], C15A···O3Aii [2.983(5) Å;(ii) 3/2-x,-1/2+y,3/2-z], C8B···O3Biii [3.149 Å; (iii) -x,-y,1-z], andC13B···O3Biii [3.116(15) Å] contacts which are shorter than the sum of thevan der Waals radii of these atoms. In the crystal structure, these dimers arelinked together by intermolecular C—H···O interaction into 1-D extendedchains along the b-axis (Fig. 3). The crystal structure is furtherstabilized by weak intermolecular π-π interactions [Cg1···Cg2i = 3.7744(6) Å; Cg2···Cg3i = 3.473(7) Å;Cg3···Cg4i = 3.458(8) Å and Cg1···Cg4 =3.670(7) Å: Cg1, Cg2, Cg3, and Cg4 are thecentroids of the C1A–C6A, C8A–C13A, C1B–C6B, and C8B–C13B benzene rings].

Related literature top

For the previous determination of this structure, see: Sarojini et al.(2007). For details of hydrogen-bond motifs, see: Bernstein et al.(1995). For the application of Schiff bases in synthesis, coordinationchemistry and biomedical activities, see: Patai (1970); Tai et al.(2003); Ittel et al. (2000); Kabeer et al. (2001); Pandeya etal. (1999); More et al. (2001); Singh & Dash (1988); Isloor etal. (2009); Pathak et al. (2000); Vazzanaa et al. (2004);Samadhiya & Halve (2001); Aydoğan et al. (2001).

Experimental top

An equimolar mixture of 4-(diethylamino)-2-hydroxybenzaldehyde (0.5 g, 2.59 mmol) and 4-methyl-3-nitro aniline (0.393 g, 2.59 mmol) in ethanol (10 mL)were refluxed for 4 h. Catalytic amount of sulfuric acid was also added. Theprecipitated solid was filtered and recrystallised from acetone to yieldorange coloured crystalline solid [0.41 g, 82 %, m.p 405 K]).

Refinement top

H atoms of the hydroxy groups were positioned by a freely rotating O—H bondand constrained with a fixed distance of 0.84 Å. The rest of the hydrogenatoms were positioned geometrically and refined using a riding model withC—H = 0.95–0.99 Å and Uiso(H) = 1.2 or 1.5 Ueq(C). A rotating-groupmodel was applied for the methyl hydrogen atoms of the methoxy groups. Rigidbond, similarity and simulation restraints were applied.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Figures top

Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoidsand the atomic numbering. Intramolecular hydrogen bond is shown as a dashedline. Open bonds show the minor component.
Fig. 2. The crystal packing of the major component of (I), viewed down theb-axis, showing dimer formation by a R22(18) motif.
Fig. 3. The crystal packing of the major component of (I), viewed down thec-axis, showing 1-D extended chain along the b-axis.

5-Diethylamino-2-[(E)-(4-methyl-3-nitrophenyl)iminomethyl]phenol top

Crystal data

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C18H21N3O3F(000) = 696
Mr = 327.38Dx = 1.340 Mg m3
Monoclinic, P21/nMelting point: 405 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 7.2777 (1) ÅCell parameters from 4554 reflections
b = 22.1792 (5) Åθ = 2.7–29.8°
c = 10.3473 (2) ŵ = 0.09 mm1
β = 103.713 (1)°T = 100 K
V = 1622.59 (5) Å3Plate, yellow
Z = 40.49 × 0.25 × 0.04 mm

Data collection

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Bruker SMART APEXII CCD area-detector
diffractometer
4744 independent reflections
Radiation source: fine-focus sealed tube3239 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.037
ϕ and ω scansθmax = 30.1°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
h = 1010
Tmin = 0.956, Tmax = 0.997k = 3131
21678 measured reflectionsl = 1414

Refinement

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Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0561P)2 + 0.1724P]
where P = (Fo2 + 2Fc2)/3
4744 reflections(Δ/σ)max < 0.001
412 parametersΔρmax = 0.21 e Å3
1197 restraintsΔρmin = 0.22 e Å3

Crystal data

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C18H21N3O3V = 1622.59 (5) Å3
Mr = 327.38Z = 4
Monoclinic, P21/nMo Kα radiation
a = 7.2777 (1) ŵ = 0.09 mm1
b = 22.1792 (5) ÅT = 100 K
c = 10.3473 (2) Å0.49 × 0.25 × 0.04 mm
β = 103.713 (1)°

Data collection

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Bruker SMART APEXII CCD area-detector
diffractometer
4744 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
3239 reflections with I > 2σ(I)
Tmin = 0.956, Tmax = 0.997Rint = 0.037
21678 measured reflections

Refinement

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R[F2 > 2σ(F2)] = 0.0431197 restraints
wR(F2) = 0.117H-atom parameters constrained
S = 1.02Δρmax = 0.21 e Å3
4744 reflectionsΔρmin = 0.22 e Å3
412 parameters

Special details

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Experimental. The low-temperature data was collected with the Oxford Cyrosystem Cobralow-temperature attachment.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

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xyzUiso*/UeqOcc. (<1)
O1A0.3739 (19)0.0973 (10)1.0926 (17)0.0234 (9)0.567(4)
H1A0.30890.07911.02620.035*0.567(4)
C1A0.5374 (9)0.1157 (3)1.0663 (5)0.0125 (7)0.567(4)
C2A0.647 (2)0.1575 (12)1.1497 (19)0.0255 (9)0.567(4)
H2AA0.61400.16821.23010.031*0.567(4)
C3A0.8077 (5)0.18510 (16)1.1189 (3)0.0255 (6)0.567(4)
C4A0.8620 (5)0.16478 (18)1.0018 (4)0.0296 (7)0.567(4)
H4AA0.97260.18030.98030.035*0.567(4)
C5A0.7531 (7)0.1227 (3)0.9210 (6)0.0252 (10)0.567(4)
H5AA0.79110.10990.84360.030*0.567(4)
C6A0.5879 (14)0.0974 (8)0.9470 (12)0.0197 (10)0.567(4)
C7A0.4817 (12)0.0550 (5)0.8538 (8)0.0179 (13)0.567(4)
H7AA0.53000.04220.78070.021*0.567(4)
N1A0.3211 (11)0.0336 (5)0.8673 (8)0.0179 (9)0.567(4)
C8A0.2039 (12)0.0048 (5)0.7729 (8)0.0250 (14)0.567(4)
C9A0.2462 (14)0.0271 (7)0.6580 (10)0.0230 (14)0.567(4)
H9AA0.36310.01710.63760.028*0.567(4)
C10A0.1184 (11)0.0637 (5)0.5730 (8)0.0221 (11)0.567(4)
C11A0.0553 (11)0.0821 (6)0.5965 (9)0.0226 (11)0.567(4)
C12A0.0955 (14)0.0564 (5)0.7096 (9)0.0309 (12)0.567(4)
H12A0.21690.06370.72560.037*0.567(4)
C13A0.0291 (11)0.0210 (5)0.8002 (9)0.0264 (12)0.567(4)
H13A0.00240.00780.87960.032*0.567(4)
N2A0.9119 (3)0.22760 (14)1.1993 (3)0.0402 (7)0.567(4)
C14A1.1461 (3)0.22808 (9)1.21715 (19)0.0262 (5)0.567(4)
H14A1.21680.23691.30930.031*0.567(4)
H14B1.19420.19081.18430.031*0.567(4)
C15A1.1392 (3)0.28153 (10)1.1233 (2)0.0327 (6)0.567(4)
H15A1.26770.29121.11580.049*0.567(4)
H15B1.08470.31651.15850.049*0.567(4)
H15C1.06090.27121.03530.049*0.567(4)
C16A0.8713 (9)0.2448 (3)1.3260 (6)0.0268 (11)0.567(4)
H16A0.99000.25801.38810.032*0.567(4)
H16B0.82320.20921.36550.032*0.567(4)
C17A0.7284 (9)0.2947 (3)1.3107 (9)0.0343 (11)0.567(4)
H17A0.70580.30471.39790.052*0.567(4)
H17B0.60970.28161.25090.052*0.567(4)
H17C0.77640.33041.27340.052*0.567(4)
C18A0.1980 (12)0.1223 (4)0.5104 (10)0.0286 (13)0.567(4)
H18A0.30710.12700.54980.043*0.567(4)
H18B0.14120.16190.50340.043*0.567(4)
H18C0.23940.10450.42160.043*0.567(4)
N3A0.184 (3)0.0827 (19)0.455 (2)0.0313 (14)0.567(4)
O2A0.3440 (11)0.0694 (3)0.4470 (8)0.0529 (17)0.567(4)
O3A0.0868 (6)0.1188 (2)0.3802 (5)0.0700 (13)0.567(4)
O1B0.398 (3)0.0963 (13)1.092 (2)0.0234 (9)0.433(4)
H1B0.35510.06801.03910.035*0.433(4)
C1B0.5589 (14)0.1191 (5)1.0618 (9)0.0306 (17)0.433(4)
C2B0.665 (3)0.1575 (15)1.155 (2)0.0255 (9)0.433(4)
H2BA0.61480.17411.22350.031*0.433(4)
C3B0.8515 (5)0.17175 (19)1.1452 (4)0.0181 (7)0.433(4)
C4B0.9079 (6)0.1517 (2)1.0301 (4)0.0218 (8)0.433(4)
H4BA1.02770.16361.01720.026*0.433(4)
C5B0.7946 (8)0.1158 (4)0.9378 (8)0.0221 (11)0.433(4)
H5BA0.83740.10340.86200.027*0.433(4)
C6B0.6180 (19)0.0966 (10)0.9512 (17)0.0197 (10)0.433(4)
C7B0.4953 (17)0.0590 (7)0.8598 (12)0.030 (2)0.433(4)
H7BA0.53340.04630.78240.036*0.433(4)
N1B0.3323 (17)0.0409 (7)0.8762 (12)0.0250 (18)0.433(4)
C8B0.2194 (14)0.0014 (6)0.7836 (10)0.0169 (13)0.433(4)
C9B0.2642 (19)0.0211 (9)0.6684 (14)0.0189 (13)0.433(4)
H9BA0.38220.01170.64910.023*0.433(4)
C10B0.1362 (14)0.0571 (6)0.5834 (10)0.0213 (14)0.433(4)
C11B0.0420 (16)0.0732 (8)0.6030 (12)0.028 (2)0.433(4)
C12B0.0749 (16)0.0544 (7)0.7258 (11)0.0330 (19)0.433(4)
H12B0.18230.06880.75360.040*0.433(4)
C13B0.0489 (16)0.0153 (7)0.8050 (13)0.033 (2)0.433(4)
H13B0.01310.00130.88000.040*0.433(4)
N2B0.9676 (3)0.20711 (11)1.2388 (2)0.0158 (5)0.433(4)
C14B1.0549 (4)0.26562 (12)1.1520 (3)0.0288 (7)0.433(4)
H14C1.00150.26541.05470.035*0.433(4)
H14D1.04820.30631.18990.035*0.433(4)
C15B1.2453 (4)0.23619 (13)1.1946 (3)0.0343 (8)0.433(4)
H15D1.33810.25931.16020.051*0.433(4)
H15E1.23840.19501.15950.051*0.433(4)
H15F1.28390.23501.29200.051*0.433(4)
C16B0.9026 (12)0.2355 (5)1.3477 (7)0.0245 (12)0.433(4)
H16C1.01440.24901.41620.029*0.433(4)
H16D0.83560.20501.38910.029*0.433(4)
C17B0.7722 (11)0.2891 (4)1.3056 (11)0.0315 (13)0.433(4)
H17D0.73390.30541.38320.047*0.433(4)
H17E0.65980.27611.23890.047*0.433(4)
H17F0.83880.32031.26740.047*0.433(4)
C18B0.1932 (17)0.1105 (6)0.5125 (13)0.0300 (17)0.433(4)
H18D0.30260.11430.55180.045*0.433(4)
H18E0.14290.15070.50140.045*0.433(4)
H18F0.23200.09070.42560.045*0.433(4)
N3B0.185 (4)0.078 (2)0.459 (3)0.0313 (14)0.433(4)
O2B0.3391 (12)0.0633 (4)0.4405 (10)0.0260 (11)0.433(4)
O3B0.0621 (6)0.10006 (19)0.3677 (5)0.0255 (7)0.433(4)

Atomic displacement parameters (Å2)

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U11U22U33U12U13U23
O1A0.020 (3)0.0286 (7)0.0251 (4)0.003 (2)0.0111 (17)0.0049 (4)
C1A0.0190 (15)0.0127 (15)0.0082 (12)0.0006 (11)0.0079 (10)0.0015 (10)
C2A0.031 (2)0.0267 (5)0.0230 (12)0.0060 (19)0.0144 (18)0.0060 (8)
C3A0.0251 (15)0.0271 (17)0.0258 (16)0.0008 (11)0.0091 (11)0.0056 (12)
C4A0.0284 (16)0.034 (2)0.0314 (18)0.0034 (12)0.0175 (13)0.0041 (13)
C5A0.026 (2)0.0303 (18)0.0211 (16)0.0044 (15)0.0082 (14)0.0067 (14)
C6A0.019 (3)0.0228 (6)0.0184 (8)0.003 (2)0.0072 (19)0.0009 (7)
C7A0.027 (2)0.0150 (18)0.0087 (19)0.0030 (15)0.0020 (15)0.0034 (16)
N1A0.0219 (19)0.018 (2)0.0152 (18)0.0029 (12)0.0063 (15)0.0020 (14)
C8A0.0211 (17)0.024 (2)0.024 (2)0.0017 (13)0.0067 (14)0.0046 (14)
C9A0.020 (3)0.035 (4)0.015 (2)0.0024 (18)0.005 (2)0.0029 (15)
C10A0.0218 (18)0.024 (2)0.0150 (15)0.0008 (14)0.0058 (11)0.0054 (13)
C11A0.019 (2)0.030 (3)0.020 (2)0.0001 (15)0.0067 (16)0.0031 (14)
C12A0.0195 (16)0.043 (2)0.026 (2)0.0028 (14)0.0026 (13)0.0072 (17)
C13A0.0192 (16)0.039 (3)0.026 (3)0.0015 (15)0.0150 (19)0.0062 (17)
N2A0.0351 (12)0.0537 (17)0.0389 (14)0.0199 (11)0.0227 (10)0.0212 (12)
C14A0.0232 (10)0.0282 (10)0.0292 (10)0.0032 (8)0.0105 (8)0.0030 (8)
C15A0.0344 (11)0.0308 (11)0.0390 (11)0.0074 (9)0.0208 (9)0.0020 (9)
C16A0.023 (2)0.033 (3)0.0247 (19)0.0049 (15)0.0064 (15)0.0040 (16)
C17A0.032 (3)0.0292 (18)0.0424 (18)0.0006 (16)0.0093 (18)0.0078 (14)
C18A0.0211 (15)0.030 (3)0.0303 (18)0.0061 (16)0.0038 (12)0.0059 (18)
N3A0.0284 (5)0.044 (5)0.0211 (13)0.0034 (11)0.0058 (7)0.0080 (7)
O2A0.028 (2)0.092 (4)0.040 (3)0.001 (2)0.0118 (18)0.028 (3)
O3A0.083 (3)0.087 (3)0.052 (2)0.0527 (19)0.0408 (18)0.047 (2)
O1B0.020 (3)0.0286 (7)0.0251 (4)0.003 (2)0.0111 (17)0.0049 (4)
C1B0.023 (2)0.029 (3)0.043 (3)0.0032 (18)0.0160 (18)0.0165 (19)
C2B0.031 (2)0.0267 (5)0.0230 (12)0.0060 (19)0.0144 (18)0.0060 (8)
C3B0.0189 (16)0.0160 (16)0.0188 (16)0.0090 (10)0.0033 (11)0.0086 (11)
C4B0.0216 (17)0.0228 (18)0.0221 (17)0.0055 (12)0.0072 (12)0.0046 (12)
C5B0.017 (2)0.029 (2)0.024 (2)0.0043 (18)0.0121 (18)0.0053 (15)
C6B0.019 (3)0.0228 (6)0.0184 (8)0.003 (2)0.0072 (19)0.0009 (7)
C7B0.031 (3)0.031 (4)0.032 (5)0.007 (2)0.017 (3)0.009 (3)
N1B0.028 (2)0.020 (3)0.021 (2)0.0010 (16)0.0066 (16)0.0077 (16)
C8B0.019 (3)0.025 (3)0.0084 (19)0.0045 (18)0.0057 (19)0.0035 (16)
C9B0.0133 (18)0.021 (2)0.018 (2)0.0030 (15)0.0052 (15)0.0053 (17)
C10B0.016 (2)0.036 (4)0.014 (2)0.0026 (17)0.008 (2)0.0050 (18)
C11B0.023 (2)0.029 (4)0.026 (2)0.0086 (18)0.0078 (17)0.0045 (19)
C12B0.019 (3)0.063 (4)0.020 (3)0.003 (2)0.011 (3)0.006 (2)
C13B0.031 (3)0.043 (4)0.021 (3)0.001 (2)0.0029 (19)0.008 (3)
N2B0.0172 (9)0.0156 (11)0.0132 (10)0.0058 (7)0.0011 (7)0.0053 (8)
C14B0.0297 (14)0.0258 (14)0.0327 (14)0.0003 (11)0.0111 (11)0.0025 (11)
C15B0.0268 (15)0.0375 (16)0.0411 (16)0.0004 (11)0.0128 (12)0.0035 (12)
C16B0.024 (3)0.030 (3)0.020 (2)0.0050 (16)0.0061 (18)0.0041 (19)
C17B0.027 (3)0.031 (2)0.038 (2)0.003 (2)0.009 (2)0.0073 (17)
C18B0.033 (2)0.027 (4)0.032 (3)0.008 (2)0.0111 (18)0.002 (2)
N3B0.0284 (5)0.044 (5)0.0211 (13)0.0034 (11)0.0058 (7)0.0080 (7)
O2B0.023 (2)0.0343 (19)0.023 (2)0.0071 (15)0.0100 (17)0.0035 (16)
O3B0.0187 (9)0.0372 (17)0.0163 (10)0.0021 (11)0.0043 (7)0.0078 (11)

Geometric parameters (Å, º)

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O1A—C1A1.346 (7)O1B—C1B1.376 (9)
O1A—H1A0.8400O1B—H1B0.8400
C1A—C2A1.384 (7)C1B—C2B1.377 (10)
C1A—C6A1.427 (7)C1B—C6B1.406 (9)
C2A—C3A1.420 (8)C2B—C3B1.418 (10)
C2A—H2AA0.9500C2B—H2BA0.9500
C3A—N2A1.363 (4)C3B—N2B1.371 (5)
C3A—C4A1.433 (5)C3B—C4B1.420 (6)
C4A—C5A1.373 (6)C4B—C5B1.361 (8)
C4A—H4AA0.9500C4B—H4BA0.9500
C5A—C6A1.409 (7)C5B—C6B1.391 (8)
C5A—H5AA0.9500C5B—H5BA0.9500
C6A—C7A1.436 (7)C6B—C7B1.409 (9)
C7A—N1A1.299 (7)C7B—N1B1.301 (9)
C7A—H7AA0.9500C7B—H7BA0.9500
N1A—C8A1.419 (7)N1B—C8B1.410 (9)
C8A—C9A1.388 (7)C8B—C13B1.363 (9)
C8A—C13A1.413 (7)C8B—C9B1.401 (9)
C9A—C10A1.383 (7)C9B—C10B1.375 (9)
C9A—H9AA0.9500C9B—H9BA0.9500
C10A—C11A1.403 (6)C10B—C11B1.405 (8)
C10A—N3A1.474 (7)C10B—N3B1.484 (9)
C11A—C12A1.394 (7)C11B—C12B1.410 (9)
C11A—C18A1.493 (7)C11B—C18B1.512 (9)
C12A—C13A1.384 (7)C12B—C13B1.373 (9)
C12A—H12A0.9500C12B—H12B0.9500
C13A—H13A0.9500C13B—H13B0.9500
N2A—C16A1.462 (6)N2B—C16B1.463 (8)
N2A—C14A1.670 (3)N2B—C14B1.779 (4)
C14A—C15A1.526 (3)C14B—C15B1.501 (4)
C14A—H14A0.9900C14B—H14C0.9900
C14A—H14B0.9900C14B—H14D0.9900
C15A—H15A0.9800C15B—H15D0.9800
C15A—H15B0.9800C15B—H15E0.9800
C15A—H15C0.9800C15B—H15F0.9800
C16A—C17A1.501 (6)C16B—C17B1.518 (8)
C16A—H16A0.9900C16B—H16C0.9900
C16A—H16B0.9900C16B—H16D0.9900
C17A—H17A0.9800C17B—H17D0.9800
C17A—H17B0.9800C17B—H17E0.9800
C17A—H17C0.9800C17B—H17F0.9800
C18A—H18A0.9800C18B—H18D0.9800
C18A—H18B0.9800C18B—H18E0.9800
C18A—H18C0.9800C18B—H18F0.9800
N3A—O3A1.219 (10)N3B—O2B1.225 (9)
N3A—O2A1.220 (7)N3B—O3B1.242 (13)
O1A—C1A—C2A119.0 (8)O1B—C1B—C2B115.9 (10)
O1A—C1A—C6A120.7 (7)O1B—C1B—C6B119.6 (10)
C2A—C1A—C6A120.0 (6)C2B—C1B—C6B123.9 (9)
C1A—C2A—C3A122.2 (8)C1B—C2B—C3B118.5 (10)
C1A—C2A—H2AA118.9C1B—C2B—H2BA120.7
C3A—C2A—H2AA118.9C3B—C2B—H2BA120.7
N2A—C3A—C2A121.9 (4)N2B—C3B—C2B121.2 (6)
N2A—C3A—C4A120.6 (3)N2B—C3B—C4B121.3 (4)
C2A—C3A—C4A117.4 (5)C2B—C3B—C4B117.3 (6)
C5A—C4A—C3A119.6 (4)C5B—C4B—C3B121.6 (5)
C5A—C4A—H4AA120.2C5B—C4B—H4BA119.2
C3A—C4A—H4AA120.2C3B—C4B—H4BA119.2
C4A—C5A—C6A123.3 (5)C4B—C5B—C6B122.0 (7)
C4A—C5A—H5AA118.4C4B—C5B—H5BA119.0
C6A—C5A—H5AA118.4C6B—C5B—H5BA119.0
C5A—C6A—C1A117.3 (6)C5B—C6B—C1B116.1 (8)
C5A—C6A—C7A118.7 (6)C5B—C6B—C7B124.6 (9)
C1A—C6A—C7A124.0 (6)C1B—C6B—C7B119.2 (8)
N1A—C7A—C6A121.5 (7)N1B—C7B—C6B123.2 (10)
N1A—C7A—H7AA119.3N1B—C7B—H7BA118.4
C6A—C7A—H7AA119.3C6B—C7B—H7BA118.4
C7A—N1A—C8A123.7 (6)C7B—N1B—C8B120.4 (9)
C9A—C8A—C13A118.3 (6)C13B—C8B—C9B116.5 (8)
C9A—C8A—N1A125.7 (6)C13B—C8B—N1B117.7 (8)
C13A—C8A—N1A116.0 (6)C9B—C8B—N1B125.8 (8)
C10A—C9A—C8A120.1 (6)C10B—C9B—C8B119.5 (9)
C10A—C9A—H9AA119.9C10B—C9B—H9BA120.2
C8A—C9A—H9AA119.9C8B—C9B—H9BA120.2
C9A—C10A—C11A124.0 (6)C9B—C10B—C11B124.3 (7)
C9A—C10A—N3A113.1 (6)C9B—C10B—N3B117.9 (7)
C11A—C10A—N3A123.0 (6)C11B—C10B—N3B117.8 (8)
C12A—C11A—C10A113.8 (6)C10B—C11B—C12B114.5 (7)
C12A—C11A—C18A119.4 (6)C10B—C11B—C18B127.6 (9)
C10A—C11A—C18A126.7 (6)C12B—C11B—C18B117.8 (9)
C13A—C12A—C11A124.5 (7)C13B—C12B—C11B119.8 (8)
C13A—C12A—H12A117.7C13B—C12B—H12B120.1
C11A—C12A—H12A117.7C11B—C12B—H12B120.1
C12A—C13A—C8A119.1 (6)C8B—C13B—C12B124.6 (9)
C12A—C13A—H13A120.5C8B—C13B—H13B117.7
C8A—C13A—H13A120.5C12B—C13B—H13B117.7
C3A—N2A—C16A121.8 (4)C3B—N2B—C16B122.2 (5)
C3A—N2A—C14A118.5 (2)C3B—N2B—C14B107.1 (2)
C16A—N2A—C14A108.5 (3)C16B—N2B—C14B107.1 (5)
C15A—C14A—N2A93.22 (16)C15B—C14B—N2B87.1 (2)
C15A—C14A—H14A113.1C15B—C14B—H14C114.1
N2A—C14A—H14A113.1N2B—C14B—H14C114.1
C15A—C14A—H14B113.1C15B—C14B—H14D114.1
N2A—C14A—H14B113.1N2B—C14B—H14D114.1
H14A—C14A—H14B110.5H14C—C14B—H14D111.3
C14A—C15A—H15A109.5C14B—C15B—H15D109.5
C14A—C15A—H15B109.5C14B—C15B—H15E109.5
H15A—C15A—H15B109.5H15D—C15B—H15E109.5
C14A—C15A—H15C109.5C14B—C15B—H15F109.5
H15A—C15A—H15C109.5H15D—C15B—H15F109.5
H15B—C15A—H15C109.5H15E—C15B—H15F109.5
N2A—C16A—C17A112.4 (4)N2B—C16B—C17B114.2 (6)
N2A—C16A—H16A109.1N2B—C16B—H16C108.7
C17A—C16A—H16A109.1C17B—C16B—H16C108.7
N2A—C16A—H16B109.1N2B—C16B—H16D108.7
C17A—C16A—H16B109.1C17B—C16B—H16D108.7
H16A—C16A—H16B107.9H16C—C16B—H16D107.6
C16A—C17A—H17A109.5C16B—C17B—H17D109.5
C16A—C17A—H17B109.5C16B—C17B—H17E109.5
H17A—C17A—H17B109.5H17D—C17B—H17E109.5
C16A—C17A—H17C109.5C16B—C17B—H17F109.5
H17A—C17A—H17C109.5H17D—C17B—H17F109.5
H17B—C17A—H17C109.5H17E—C17B—H17F109.5
C11A—C18A—H18A109.5C11B—C18B—H18D109.5
C11A—C18A—H18B109.5C11B—C18B—H18E109.5
H18A—C18A—H18B109.5H18D—C18B—H18E109.5
C11A—C18A—H18C109.5C11B—C18B—H18F109.5
H18A—C18A—H18C109.5H18D—C18B—H18F109.5
H18B—C18A—H18C109.5H18E—C18B—H18F109.5
O3A—N3A—O2A122.4 (11)O2B—N3B—O3B120.2 (13)
O3A—N3A—C10A117.3 (8)O2B—N3B—C10B118.2 (9)
O2A—N3A—C10A119.3 (7)O3B—N3B—C10B120.4 (11)
C1B—O1B—H1B109.5
O1A—C1A—C2A—C3A171 (2)O1B—C1B—C2B—C3B166 (3)
C6A—C1A—C2A—C3A2 (3)C6B—C1B—C2B—C3B5 (4)
C1A—C2A—C3A—N2A178.0 (16)C1B—C2B—C3B—N2B176 (2)
C1A—C2A—C3A—C4A5 (3)C1B—C2B—C3B—C4B8 (4)
N2A—C3A—C4A—C5A178.9 (4)N2B—C3B—C4B—C5B178.9 (4)
C2A—C3A—C4A—C5A3.6 (15)C2B—C3B—C4B—C5B6 (2)
C3A—C4A—C5A—C6A0.3 (12)C3B—C4B—C5B—C6B0.2 (16)
C4A—C5A—C6A—C1A2 (2)C4B—C5B—C6B—C1B3 (3)
C4A—C5A—C6A—C7A178.3 (10)C4B—C5B—C6B—C7B179.4 (17)
O1A—C1A—C6A—C5A174.7 (16)O1B—C1B—C6B—C5B172 (2)
C2A—C1A—C6A—C5A1 (2)C2B—C1B—C6B—C5B0 (4)
O1A—C1A—C6A—C7A6 (2)O1B—C1B—C6B—C7B11 (3)
C2A—C1A—C6A—C7A179 (2)C2B—C1B—C6B—C7B178 (3)
C5A—C6A—C7A—N1A174.8 (13)C5B—C6B—C7B—N1B179 (2)
C1A—C6A—C7A—N1A6 (2)C1B—C6B—C7B—N1B4 (3)
C6A—C7A—N1A—C8A175.0 (14)C6B—C7B—N1B—C8B177.5 (19)
C7A—N1A—C8A—C9A3 (2)C7B—N1B—C8B—C13B179.1 (17)
C7A—N1A—C8A—C13A176.6 (12)C7B—N1B—C8B—C9B1 (3)
C13A—C8A—C9A—C10A0 (2)C13B—C8B—C9B—C10B1 (3)
N1A—C8A—C9A—C10A179.3 (13)N1B—C8B—C9B—C10B176.9 (17)
C8A—C9A—C10A—C11A2 (2)C8B—C9B—C10B—C11B1 (3)
C8A—C9A—C10A—N3A179 (2)C8B—C9B—C10B—N3B177 (3)
C9A—C10A—C11A—C12A4.5 (19)C9B—C10B—C11B—C12B6 (3)
N3A—C10A—C11A—C12A177 (2)N3B—C10B—C11B—C12B177 (3)
C9A—C10A—C11A—C18A178.9 (13)C9B—C10B—C11B—C18B177.7 (18)
N3A—C10A—C11A—C18A0 (3)N3B—C10B—C11B—C18B1 (4)
C10A—C11A—C12A—C13A6.6 (19)C10B—C11B—C12B—C13B10 (2)
C18A—C11A—C12A—C13A176.6 (12)C18B—C11B—C12B—C13B173.2 (15)
C11A—C12A—C13A—C8A6 (2)C9B—C8B—C13B—C12B3 (3)
C9A—C8A—C13A—C12A2.3 (19)N1B—C8B—C13B—C12B178.4 (16)
N1A—C8A—C13A—C12A177.4 (11)C11B—C12B—C13B—C8B9 (3)
C2A—C3A—N2A—C16A3.6 (16)C2B—C3B—N2B—C16B4 (2)
C4A—C3A—N2A—C16A173.8 (3)C4B—C3B—N2B—C16B170.9 (5)
C2A—C3A—N2A—C14A143.3 (15)C2B—C3B—N2B—C14B128 (2)
C4A—C3A—N2A—C14A34.1 (4)C4B—C3B—N2B—C14B47.0 (3)
C3A—N2A—C14A—C15A102.7 (3)C3B—N2B—C14B—C15B111.2 (2)
C16A—N2A—C14A—C15A112.8 (4)C16B—N2B—C14B—C15B116.1 (4)
C3A—N2A—C16A—C17A88.1 (6)C3B—N2B—C16B—C17B74.0 (9)
C14A—N2A—C16A—C17A128.8 (5)C14B—N2B—C16B—C17B49.9 (8)
C9A—C10A—N3A—O3A175 (3)C9B—C10B—N3B—O2B2 (6)
C11A—C10A—N3A—O3A4 (5)C11B—C10B—N3B—O2B179 (4)
C9A—C10A—N3A—O2A5 (5)C9B—C10B—N3B—O3B166 (4)
C11A—C10A—N3A—O2A174 (3)C11B—C10B—N3B—O3B11 (6)

Hydrogen-bond geometry (Å, º)

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D—H···AD—HH···AD···AD—H···A
O1A—H1A···N1A0.841.952.68 (2)144
C12A—H12A···O1Ai0.952.533.329 (19)141
C15A—H15A···O3Aii0.982.262.983 (5)130

Symmetry codes: (i) x, y, z+2; (ii) x+3/2, y+1/2, z+3/2.

Experimental details

Crystal data
Chemical formulaC18H21N3O3
Mr327.38
Crystal system, space groupMonoclinic, P21/n
Temperature (K)100
a, b, c (Å)7.2777 (1), 22.1792 (5), 10.3473 (2)
β (°) 103.713 (1)
V3)1622.59 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.49 × 0.25 × 0.04
Data collection
DiffractometerBruker SMART APEXII CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.956, 0.997
No. of measured, independent and
observed [I > 2σ(I)] reflections
21678, 4744, 3239
Rint0.037
(sin θ/λ)max1)0.706
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.117, 1.02
No. of reflections4744
No. of parameters412
No. of restraints1197
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.21, 0.22

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º)

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D—H···AD—HH···AD···AD—H···A
O1A—H1A···N1A0.84001.95002.68(2)144.00
C12A—H12A···O1Ai0.95002.53003.329(19)141.00
C15A—H15A···O3Aii0.98002.26002.983(5)130.00

Symmetry codes: (i) x, y, z+2; (ii) x+3/2, y+1/2, z+3/2.


5-Diethyl­amino-2-[(E)-(4-methyl-3-nitro­phenyl)­imino­meth­yl]phenol: a redetermination (2024)

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