(E)-2-{[(5-Chloro-2-meth­oxy­phen­yl)imino]­meth­yl}-4-nitro­phenol

The title compound, C₁₄H₁₁ClN₂O₄, is a Schiff base. Its mol­ecule is approximatelly planar, with a maximum deviation of 0.096 (4) Å from planarity for the methyl C atom of the meth­oxy group. The dihedral angle between the 5-chloro-2-meth­oxy­phenyl ring and the phenol ring is 2.40 (10)°. In the crystal structure, inter­molecular C—H...O hydrogen bonds and π–π stacking inter­actions consolidate the crystal packing.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.042
• wR factor = 0.106
• Data-to-parameter ratio = 13.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......     25.054 Check
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      4.548 Check
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      2.059 Check
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Note

Alert level G
PLAT063_ALERT_4_G Crystal Size Likely too Large for Beam Size ....       0.71 mm
PLAT128_ALERT_4_G Alternate Setting for Input Space Group  P21/c        P21/n Note
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   4 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   4 ALERT level G = General information/check it is not something unexpected

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).

(E)-2-{[(5-Chloro-2-methoxyphenyl)imino]methyl}-4-nitrophenol

Crystal data

C14H11ClN2O4	F(000) = 632
Mr = 306.70	Dx = 1.490 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.3727 (9) Å	Cell parameters from 453 reflections
b = 4.8669 (4) Å	θ = 2.8–26.5°
c = 22.3233 (13) Å	µ = 0.30 mm^−1
β = 118.859 (9)°	T = 293 K
V = 1367.60 (19) Å^3	Stick, orange
Z = 4	0.71 × 0.30 × 0.05 mm

Data collection

Stoe IPDS 2 diffractometer	1527 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.048
Detector resolution: 6.67 pixels mm^-1	θmax = 26.0°, θmin = 1.6°
rotation method scans	h = −17→17
10508 measured reflections	k = −5→6
2679 independent reflections	l = −27→27

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.106	w = 1/[σ^2(Fo^2) + (0.0521P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.94	(Δ/σ)max < 0.001
2679 reflections	Δρmax = 0.13 e Å^−3
194 parameters	Δρmin = −0.18 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
N1	0.52416 (15)	1.7724 (4)	0.62967 (10)	0.0621 (5)
N2	0.21754 (15)	0.8722 (4)	0.46453 (9)	0.0548 (5)
O1	0.55958 (16)	1.7922 (4)	0.58993 (10)	0.0904 (6)
O2	0.55351 (15)	1.9177 (4)	0.68000 (9)	0.0819 (6)
O3	0.20231 (15)	1.0208 (4)	0.57164 (11)	0.0773 (6)
O4	0.06221 (14)	0.5188 (4)	0.43672 (9)	0.0827 (6)
Cl5	0.24175 (6)	0.56490 (18)	0.25064 (4)	0.0910 (3)
C1	0.40681 (17)	1.4090 (5)	0.55759 (11)	0.0532 (6)
H1	0.437436	1.426791	0.529395	0.064*
C2	0.44190 (17)	1.5699 (5)	0.61496 (10)	0.0516 (5)
C3	0.39872 (19)	1.5455 (5)	0.65855 (11)	0.0627 (6)
H3	0.423828	1.653642	0.697654	0.075*
C4	0.3190 (2)	1.3609 (5)	0.64320 (12)	0.0678 (7)
H4	0.289785	1.344033	0.672215	0.081*
C5	0.28050 (19)	1.1971 (5)	0.58499 (12)	0.0572 (6)
C6	0.32592 (17)	1.2200 (5)	0.54146 (10)	0.0504 (5)
C7	0.29030 (18)	1.0508 (5)	0.48111 (11)	0.0567 (6)
H7	0.321734	1.073469	0.453501	0.068*
C8	0.18388 (18)	0.7040 (5)	0.40607 (11)	0.0532 (5)
C9	0.22709 (19)	0.7136 (5)	0.36221 (11)	0.0593 (6)
H9	0.281618	0.836500	0.370621	0.071*
C10	0.18942 (19)	0.5422 (5)	0.30648 (12)	0.0612 (6)
C11	0.1098 (2)	0.3565 (5)	0.29338 (12)	0.0676 (7)
H11	0.085619	0.239788	0.255838	0.081*
C12	0.0665 (2)	0.3450 (5)	0.33613 (12)	0.0675 (7)
H12	0.012689	0.219286	0.327311	0.081*
C13	0.10144 (18)	0.5171 (5)	0.39218 (12)	0.0588 (6)
C14	−0.0258 (3)	0.3385 (8)	0.42157 (18)	0.1160 (13)
H14A	−0.046574	0.357148	0.456270	0.139*
H14B	−0.084445	0.386065	0.377899	0.139*
H14C	−0.004954	0.151962	0.420421	0.139*
H15	0.190 (3)	0.938 (7)	0.5353 (18)	0.110 (12)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0579 (12)	0.0628 (14)	0.0635 (12)	−0.0097 (10)	0.0277 (10)	−0.0060 (11)
N2	0.0572 (11)	0.0488 (12)	0.0588 (11)	−0.0081 (10)	0.0282 (9)	−0.0033 (9)
O1	0.0925 (14)	0.1061 (17)	0.0973 (14)	−0.0438 (12)	0.0655 (12)	−0.0278 (12)
O2	0.0839 (13)	0.0805 (13)	0.0724 (11)	−0.0243 (10)	0.0307 (10)	−0.0242 (11)
O3	0.0841 (13)	0.0825 (15)	0.0841 (13)	−0.0298 (11)	0.0555 (11)	−0.0121 (11)
O4	0.0831 (12)	0.0952 (15)	0.0797 (11)	−0.0399 (11)	0.0470 (10)	−0.0193 (10)
Cl5	0.1001 (6)	0.1078 (6)	0.0782 (4)	0.0006 (5)	0.0534 (4)	−0.0180 (4)
C1	0.0551 (13)	0.0577 (15)	0.0540 (12)	−0.0050 (12)	0.0319 (10)	0.0000 (11)
C2	0.0520 (13)	0.0527 (14)	0.0506 (12)	−0.0054 (11)	0.0252 (10)	0.0012 (11)
C3	0.0777 (17)	0.0616 (17)	0.0530 (13)	−0.0057 (14)	0.0349 (12)	−0.0048 (12)
C4	0.0865 (18)	0.0710 (19)	0.0637 (15)	−0.0118 (15)	0.0504 (14)	−0.0023 (13)
C5	0.0620 (14)	0.0535 (15)	0.0636 (14)	−0.0066 (12)	0.0364 (12)	0.0032 (12)
C6	0.0518 (13)	0.0535 (15)	0.0498 (11)	−0.0027 (11)	0.0276 (10)	0.0022 (11)
C7	0.0593 (14)	0.0601 (15)	0.0565 (13)	−0.0062 (13)	0.0324 (11)	−0.0009 (12)
C8	0.0564 (13)	0.0446 (13)	0.0543 (12)	0.0012 (11)	0.0234 (11)	0.0014 (11)
C9	0.0606 (14)	0.0536 (15)	0.0625 (14)	−0.0020 (12)	0.0288 (12)	−0.0045 (12)
C10	0.0642 (15)	0.0584 (16)	0.0579 (14)	0.0083 (13)	0.0271 (12)	−0.0004 (12)
C11	0.0743 (17)	0.0558 (17)	0.0550 (14)	0.0054 (13)	0.0171 (13)	−0.0070 (12)
C12	0.0689 (16)	0.0529 (16)	0.0669 (16)	−0.0100 (13)	0.0218 (13)	−0.0019 (13)
C13	0.0575 (14)	0.0529 (16)	0.0587 (13)	−0.0042 (12)	0.0224 (12)	0.0032 (11)
C14	0.104 (3)	0.149 (3)	0.113 (2)	−0.071 (2)	0.067 (2)	−0.038 (2)

Geometric parameters (Å, º)

N1—O2	1.218 (2)	C4—H4	0.9300
N1—O1	1.221 (2)	C5—C6	1.413 (3)
N1—C2	1.450 (3)	C6—C7	1.445 (3)
N2—C7	1.270 (3)	C7—H7	0.9300
N2—C8	1.413 (3)	C8—C9	1.391 (3)
O3—C5	1.328 (3)	C8—C13	1.405 (3)
O3—H15	0.84 (3)	C9—C10	1.374 (3)
O4—C13	1.359 (3)	C9—H9	0.9300
O4—C14	1.439 (3)	C10—C11	1.374 (4)
Cl5—C10	1.743 (2)	C11—C12	1.369 (4)
C1—C2	1.373 (3)	C11—H11	0.9300
C1—C6	1.387 (3)	C12—C13	1.383 (3)
C1—H1	0.9300	C12—H12	0.9300
C2—C3	1.389 (3)	C14—H14A	0.9600
C3—C4	1.363 (3)	C14—H14B	0.9600
C3—H3	0.9300	C14—H14C	0.9600
C4—C5	1.391 (3)
O2—N1—O1	123.0 (2)	C6—C7—H7	118.9
O2—N1—C2	119.0 (2)	C9—C8—C13	118.8 (2)
O1—N1—C2	118.00 (19)	C9—C8—N2	124.1 (2)
C7—N2—C8	122.17 (18)	C13—C8—N2	117.09 (19)
C5—O3—H15	107 (2)	C10—C9—C8	120.2 (2)
C13—O4—C14	116.9 (2)	C10—C9—H9	119.9
C2—C1—C6	120.34 (19)	C8—C9—H9	119.9
C2—C1—H1	119.8	C11—C10—C9	121.1 (2)
C6—C1—H1	119.8	C11—C10—Cl5	119.48 (19)
C1—C2—C3	121.2 (2)	C9—C10—Cl5	119.5 (2)
C1—C2—N1	119.43 (18)	C12—C11—C10	119.4 (2)
C3—C2—N1	119.4 (2)	C12—C11—H11	120.3
C4—C3—C2	119.1 (2)	C10—C11—H11	120.3
C4—C3—H3	120.5	C11—C12—C13	121.1 (2)
C2—C3—H3	120.5	C11—C12—H12	119.4
C3—C4—C5	121.3 (2)	C13—C12—H12	119.4
C3—C4—H4	119.3	O4—C13—C12	124.6 (2)
C5—C4—H4	119.3	O4—C13—C8	116.0 (2)
O3—C5—C4	119.5 (2)	C12—C13—C8	119.4 (2)
O3—C5—C6	121.2 (2)	O4—C14—H14A	109.5
C4—C5—C6	119.3 (2)	O4—C14—H14B	109.5
C1—C6—C5	118.8 (2)	H14A—C14—H14B	109.5
C1—C6—C7	119.69 (18)	O4—C14—H14C	109.5
C5—C6—C7	121.5 (2)	H14A—C14—H14C	109.5
N2—C7—C6	122.21 (19)	H14B—C14—H14C	109.5
N2—C7—H7	118.9
C6—C1—C2—C3	0.9 (3)	C5—C6—C7—N2	−0.7 (3)
C6—C1—C2—N1	−178.0 (2)	C7—N2—C8—C9	1.0 (3)
O2—N1—C2—C1	178.7 (2)	C7—N2—C8—C13	−178.9 (2)
O1—N1—C2—C1	0.0 (3)	C13—C8—C9—C10	−0.1 (3)
O2—N1—C2—C3	−0.2 (3)	N2—C8—C9—C10	180.0 (2)
O1—N1—C2—C3	−178.9 (2)	C8—C9—C10—C11	−0.8 (4)
C1—C2—C3—C4	−1.0 (4)	C8—C9—C10—Cl5	178.00 (18)
N1—C2—C3—C4	177.9 (2)	C9—C10—C11—C12	0.9 (4)
C2—C3—C4—C5	0.1 (4)	Cl5—C10—C11—C12	−177.96 (19)
C3—C4—C5—O3	−179.6 (2)	C10—C11—C12—C13	0.0 (4)
C3—C4—C5—C6	0.9 (4)	C14—O4—C13—C12	−3.6 (4)
C2—C1—C6—C5	0.1 (3)	C14—O4—C13—C8	177.0 (3)
C2—C1—C6—C7	−179.6 (2)	C11—C12—C13—O4	179.7 (2)
O3—C5—C6—C1	179.5 (2)	C11—C12—C13—C8	−1.0 (4)
C4—C5—C6—C1	−1.0 (3)	C9—C8—C13—O4	−179.6 (2)
O3—C5—C6—C7	−0.8 (4)	N2—C8—C13—O4	0.2 (3)
C4—C5—C6—C7	178.7 (2)	C9—C8—C13—C12	1.0 (3)
C8—N2—C7—C6	−179.0 (2)	N2—C8—C13—C12	−179.1 (2)
C1—C6—C7—N2	179.1 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H15···N2	0.84 (3)	1.84 (3)	2.606 (3)	151 (3)
C7—H7···O1^i	0.93	2.42	3.325 (3)	163
C14—H14A···O4^ii	0.96	2.58	3.516 (4)	166

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