4-Meth­oxy-N-[3-(2-nitro­phen­yl)allyl­idene]aniline

The mol­ecule of the title compound, C₁₆H₁₄N₂O₃, is slightly non-planar, with a dihedral angle of 4.01 (1)° between the two benzene rings. In the crystal structure, mol­ecules are linked into chains by C—H...O inter­molecular hydrogen bonds. The crystal structure is stabilized by C—H...π and π–π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.056
• wR factor = 0.144
• Data-to-parameter ratio = 13.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N2
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C16 H14 N2 O3

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   3 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
   0 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

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Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

4-Methoxy-N-[3-(2-nitrophenyl)allylidene]aniline

Crystal data

C16H14N2O3	F(000) = 592
Mr = 282.29	Dx = 1.329 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.4308 (15) Å	Cell parameters from 958 reflections
b = 7.8556 (16) Å	θ = 2.8–20.7°
c = 24.569 (5) Å	µ = 0.09 mm^−1
β = 100.322 (6)°	T = 293 K
V = 1411.0 (5) Å^3	Plate, yellow
Z = 4	0.37 × 0.16 × 0.09 mm

Data collection

Siemens SMART 1000 CCD area-detector diffractometer	2767 independent reflections
Radiation source: fine-focus sealed tube	1626 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
Detector resolution: 8.33 pixels mm^-1	θmax = 26.0°, θmin = 1.7°
ω scans	h = −9→8
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −9→9
Tmin = 0.966, Tmax = 0.992	l = −16→30
7494 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.056	H-atom parameters constrained
wR(F^2) = 0.144	w = 1/[σ^2(Fo^2) + (0.0553P)^2 + 0.1719P] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max < 0.001
2767 reflections	Δρmax = 0.19 e Å^−3
205 parameters	Δρmin = −0.13 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0088 (16)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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
O1	0.1456 (3)	−0.1551 (3)	−0.24872 (9)	0.1138 (9)
O2	−0.0160 (3)	−0.2517 (3)	−0.19281 (8)	0.0966 (8)
O3	−0.5184 (2)	−0.0956 (2)	0.16355 (7)	0.0648 (5)
N1	0.0079 (3)	−0.2985 (3)	0.04202 (8)	0.0556 (6)
N2	0.1306 (3)	−0.2311 (3)	−0.20712 (9)	0.0691 (7)
C1	−0.2990 (3)	−0.1760 (3)	0.04347 (9)	0.0510 (6)
H1B	−0.3217	−0.1643	0.0052	0.050 (6)*
C2	−0.4314 (3)	−0.1270 (3)	0.07307 (10)	0.0515 (6)
H2A	−0.5425	−0.0842	0.0547	0.059 (7)*
C3	−0.3988 (3)	−0.1416 (3)	0.13003 (9)	0.0468 (6)
C4	−0.2349 (3)	−0.2102 (3)	0.15656 (10)	0.0535 (6)
H4A	−0.2122	−0.2215	0.1949	0.059 (7)*
C5	−0.1056 (3)	−0.2620 (3)	0.12661 (9)	0.0511 (6)
H5A	0.0022	−0.3115	0.1448	0.057 (7)*
C6	−0.1335 (3)	−0.2419 (3)	0.06930 (8)	0.0438 (6)
C7	0.0212 (3)	−0.2475 (3)	−0.00590 (10)	0.0531 (6)
H7A	−0.0611	−0.1661	−0.0228	0.070 (8)*
C8	0.1580 (3)	−0.3100 (3)	−0.03530 (10)	0.0517 (6)
H8A	0.2387	−0.3921	−0.0180	0.056 (7)*
C9	0.1772 (3)	−0.2604 (3)	−0.08489 (9)	0.0562 (7)
H9A	0.0979	−0.1761	−0.1014	0.058 (7)*
C10	0.3118 (3)	−0.3240 (3)	−0.11673 (9)	0.0478 (6)
C11	0.4721 (3)	−0.4023 (3)	−0.08999 (11)	0.0575 (7)
H11A	0.4896	−0.4158	−0.0518	0.065 (7)*
C12	0.6048 (4)	−0.4605 (3)	−0.11782 (13)	0.0695 (8)
H12A	0.7081	−0.5151	−0.0987	0.078 (9)*
C13	0.5838 (4)	−0.4377 (4)	−0.17428 (14)	0.0774 (9)
H13A	0.6742	−0.4748	−0.1932	0.096 (10)*
C14	0.4299 (4)	−0.3599 (4)	−0.20232 (12)	0.0693 (8)
H14A	0.4154	−0.3434	−0.2403	0.079 (8)*
C15	0.2961 (3)	−0.3064 (3)	−0.17384 (10)	0.0522 (6)
C16	−0.6852 (3)	−0.0182 (4)	0.13887 (12)	0.0728 (8)
H16A	−0.7551	0.0090	0.1670	0.073 (8)*
H16B	−0.6602	0.0841	0.1202	0.094 (10)*
H16C	−0.7534	−0.0955	0.1127	0.112 (12)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.1019 (16)	0.179 (3)	0.0568 (13)	−0.0265 (15)	0.0037 (12)	0.0409 (15)
O2	0.0644 (13)	0.158 (2)	0.0699 (14)	0.0031 (13)	0.0194 (11)	0.0078 (14)
O3	0.0606 (11)	0.0854 (13)	0.0544 (11)	0.0118 (9)	0.0268 (9)	−0.0001 (9)
N1	0.0625 (13)	0.0689 (14)	0.0399 (11)	0.0039 (10)	0.0215 (10)	0.0001 (10)
N2	0.0704 (16)	0.0992 (19)	0.0388 (12)	−0.0164 (13)	0.0127 (12)	0.0019 (12)
C1	0.0603 (15)	0.0627 (16)	0.0309 (12)	−0.0020 (12)	0.0109 (11)	0.0035 (11)
C2	0.0513 (14)	0.0581 (16)	0.0453 (14)	0.0042 (12)	0.0094 (12)	0.0058 (12)
C3	0.0501 (14)	0.0510 (15)	0.0429 (13)	−0.0058 (11)	0.0177 (11)	−0.0039 (11)
C4	0.0569 (15)	0.0732 (17)	0.0323 (13)	−0.0022 (13)	0.0130 (11)	0.0000 (12)
C5	0.0504 (14)	0.0665 (16)	0.0371 (13)	0.0024 (12)	0.0101 (11)	0.0036 (12)
C6	0.0504 (13)	0.0476 (14)	0.0360 (12)	−0.0032 (11)	0.0147 (11)	−0.0022 (11)
C7	0.0610 (15)	0.0575 (16)	0.0442 (14)	0.0018 (13)	0.0190 (12)	0.0005 (12)
C8	0.0601 (15)	0.0542 (15)	0.0447 (14)	0.0010 (12)	0.0195 (12)	−0.0013 (12)
C9	0.0614 (15)	0.0683 (17)	0.0430 (14)	0.0033 (14)	0.0205 (12)	0.0019 (13)
C10	0.0541 (14)	0.0510 (14)	0.0420 (13)	−0.0068 (11)	0.0189 (11)	−0.0012 (11)
C11	0.0636 (16)	0.0594 (16)	0.0527 (17)	−0.0013 (13)	0.0188 (13)	0.0045 (13)
C12	0.0653 (18)	0.0620 (18)	0.086 (2)	0.0041 (14)	0.0276 (17)	−0.0009 (16)
C13	0.075 (2)	0.079 (2)	0.091 (2)	−0.0028 (17)	0.0493 (19)	−0.0162 (18)
C14	0.082 (2)	0.083 (2)	0.0518 (17)	−0.0200 (16)	0.0347 (16)	−0.0166 (15)
C15	0.0567 (15)	0.0600 (16)	0.0432 (13)	−0.0150 (12)	0.0180 (12)	−0.0077 (12)
C16	0.0527 (16)	0.087 (2)	0.084 (2)	0.0088 (15)	0.0259 (16)	−0.002 (2)

Geometric parameters (Å, º)

O1—N2	1.206 (3)	C7—H7A	0.9299
O2—N2	1.213 (2)	C8—C9	1.311 (3)
O3—C3	1.365 (2)	C8—H8A	0.9299
O3—C16	1.415 (3)	C9—C10	1.463 (3)
N1—C7	1.264 (3)	C9—H9A	0.9301
N1—C6	1.415 (3)	C10—C15	1.394 (3)
N2—C15	1.474 (3)	C10—C11	1.396 (3)
C1—C2	1.379 (3)	C11—C12	1.375 (3)
C1—C6	1.380 (3)	C11—H11A	0.9299
C1—H1B	0.9298	C12—C13	1.380 (4)
C2—C3	1.382 (3)	C12—H12A	0.9299
C2—H2A	0.9300	C13—C14	1.369 (4)
C3—C4	1.383 (3)	C13—H13A	0.9300
C4—C5	1.372 (3)	C14—C15	1.380 (3)
C4—H4A	0.9300	C14—H14A	0.9299
C5—C6	1.395 (3)	C16—H16A	0.9600
C5—H5A	0.9299	C16—H16B	0.9600
C7—C8	1.435 (3)	C16—H16C	0.9601
C3—O3—C16	118.1 (2)	C7—C8—H8A	117.6
C7—N1—C6	122.0 (2)	C8—C9—C10	126.5 (2)
O1—N2—O2	122.4 (3)	C8—C9—H9A	116.8
O1—N2—C15	118.3 (2)	C10—C9—H9A	116.8
O2—N2—C15	119.3 (2)	C15—C10—C11	115.3 (2)
C2—C1—C6	121.6 (2)	C15—C10—C9	124.2 (2)
C2—C1—H1B	119.2	C11—C10—C9	120.4 (2)
C6—C1—H1B	119.2	C12—C11—C10	122.7 (3)
C1—C2—C3	119.9 (2)	C12—C11—H11A	118.7
C1—C2—H2A	120.0	C10—C11—H11A	118.6
C3—C2—H2A	120.1	C11—C12—C13	119.7 (3)
O3—C3—C2	125.0 (2)	C11—C12—H12A	120.2
O3—C3—C4	115.6 (2)	C13—C12—H12A	120.2
C2—C3—C4	119.3 (2)	C14—C13—C12	119.9 (3)
C5—C4—C3	120.3 (2)	C14—C13—H13A	120.1
C5—C4—H4A	119.8	C12—C13—H13A	120.1
C3—C4—H4A	119.9	C13—C14—C15	119.6 (3)
C4—C5—C6	121.1 (2)	C13—C14—H14A	120.2
C4—C5—H5A	119.5	C15—C14—H14A	120.2
C6—C5—H5A	119.4	C14—C15—C10	122.9 (2)
C1—C6—C5	117.7 (2)	C14—C15—N2	116.5 (2)
C1—C6—N1	125.19 (19)	C10—C15—N2	120.6 (2)
C5—C6—N1	117.0 (2)	O3—C16—H16A	109.4
N1—C7—C8	122.8 (2)	O3—C16—H16B	109.6
N1—C7—H7A	118.7	H16A—C16—H16B	109.5
C8—C7—H7A	118.6	O3—C16—H16C	109.4
C9—C8—C7	124.8 (2)	H16A—C16—H16C	109.5
C9—C8—H8A	117.6	H16B—C16—H16C	109.5
C6—C1—C2—C3	0.8 (4)	C8—C9—C10—C15	160.6 (2)
C16—O3—C3—C2	−3.6 (4)	C8—C9—C10—C11	−22.0 (4)
C16—O3—C3—C4	177.5 (2)	C15—C10—C11—C12	−0.8 (3)
C1—C2—C3—O3	179.2 (2)	C9—C10—C11—C12	−178.4 (2)
C1—C2—C3—C4	−1.9 (4)	C10—C11—C12—C13	1.8 (4)
O3—C3—C4—C5	179.5 (2)	C11—C12—C13—C14	−1.0 (4)
C2—C3—C4—C5	0.5 (4)	C12—C13—C14—C15	−0.6 (4)
C3—C4—C5—C6	2.0 (4)	C13—C14—C15—C10	1.6 (4)
C2—C1—C6—C5	1.7 (3)	C13—C14—C15—N2	−177.2 (2)
C2—C1—C6—N1	178.6 (2)	C11—C10—C15—C14	−0.9 (3)
C4—C5—C6—C1	−3.1 (3)	C9—C10—C15—C14	176.6 (2)
C4—C5—C6—N1	179.7 (2)	C11—C10—C15—N2	177.9 (2)
C7—N1—C6—C1	22.4 (4)	C9—C10—C15—N2	−4.6 (4)
C7—N1—C6—C5	−160.7 (2)	O1—N2—C15—C14	−31.0 (4)
C6—N1—C7—C8	−176.7 (2)	O2—N2—C15—C14	146.8 (2)
N1—C7—C8—C9	−179.8 (2)	O1—N2—C15—C10	150.1 (2)
C7—C8—C9—C10	−178.4 (2)	O2—N2—C15—C10	−32.1 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···Cg1^i	0.93	3.16	3.656	115
C16—H16B···Cg2^i	0.96	2.82	3.586	137
C9—H9A···O2	0.93	2.33	2.781 (3)	109
C13—H13A···O1^ii	0.93	2.55	3.450 (4)	162
C14—H14A···O3^iii	0.93	2.54	3.403 (3)	154

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