Methyl 4-(4-methoxy­benzyl­idene­methyl)-3,5-di­nitro­benzoate

Aravindan, P.G.; Selvanayagam, S.; Velmurugan, D.; Ravikumar, K.; Saravanan, S.; Srinivasan, P.C.

doi:10.1107/S1600536804025875

Methyl 4-(4-methoxybenzylidenemethyl)-3,5-dinitrobenzoate

P. G. Aravindan, S. Selvanayagam, D. Velmurugan, K. Ravikumar, S. Saravanan and P. C. Srinivasan

The title compound, C₁₇H₁₄N₂O₇, is a trans-stilbene and the dihedral angle between the benzene rings is 58.2 (1)°. The orientation of the nitro groups on the benzene ring is consistent with minimum steric interaction. In the solid state, inversion-related molecules are linked into dimers through C—H

O interactions and the translated dimers are linked via C—H

O interactions, thus forming a continuous chain running along one of the diagonals (011) of the bc plane.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804025875/bt6541sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536804025875/bt6541Isup2.hkl Contains datablock I

CCDC reference: 255912

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.002 Å
R factor = 0.046
wR factor = 0.145
Data-to-parameter ratio = 16.0

checkCIF/PLATON results

No syntax errors found



Alert level A
DIFF020_ALERT_1_A  _diffrn_standards_interval_count and
            _diffrn_standards_interval_time are missing. Number of measurements
            between standards or time (min) between standards.
DIFF022_ALERT_1_A  _diffrn_standards_decay_% is missing
            Percentage decrease in standards intensity.
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.91

Alert level C
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors  for         N2

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

   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
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1997) and PLATON (Spek, 1990); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

methyl 4-(4-methoxybenzylidenemethyl)-3,5-dinitrobenzoate top

Crystal data top

C₁₇H₁₄N₂O₇	F(000) = 744
M_r = 358.30	D_x = 1.443 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2ybc	Cell parameters from 2638 reflections
a = 12.0496 (8) Å	θ = 2.5–27.9°
b = 7.0295 (5) Å	µ = 0.11 mm⁻¹
c = 19.8296 (13) Å	T = 293 K
β = 100.856 (1)°	Block, pale yellow
V = 1649.56 (19) Å³	0.26 × 0.20 × 0.12 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	2871 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.019
Graphite monochromator	θ_max = 28.0°, θ_min = 1.7°
ω scans	h = −15→7
9977 measured reflections	k = −9→9
3785 independent reflections	l = −23→25

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.145	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0837P)² + 0.21P] where P = (F_o² + 2F_c²)/3
3785 reflections	(Δ/σ)_max < 0.001
237 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.06847 (10)	−0.1636 (2)	−0.03636 (7)	0.0699 (4)
O2	0.20174 (11)	−0.30039 (19)	0.03466 (6)	0.0645 (4)
O3	0.56287 (10)	0.33777 (18)	0.03366 (7)	0.0606 (3)
O4	0.43519 (17)	0.3772 (3)	0.09286 (9)	0.1134 (7)
O5	0.45347 (10)	0.1100 (2)	−0.20066 (6)	0.0622 (4)
O6	0.28578 (11)	−0.03416 (17)	−0.22970 (5)	0.0532 (3)
O7	0.14191 (12)	0.0517 (2)	0.39076 (6)	0.0699 (4)
N1	0.16656 (11)	−0.1796 (2)	−0.00728 (6)	0.0461 (3)
N2	0.46960 (13)	0.3058 (2)	0.04615 (7)	0.0533 (4)
C1	0.31297 (12)	0.0692 (2)	0.02363 (7)	0.0385 (3)
C2	0.24788 (12)	−0.0431 (2)	−0.02679 (7)	0.0388 (3)
C3	0.25820 (12)	−0.0464 (2)	−0.09501 (7)	0.0404 (3)
H3	0.2092	−0.1190	−0.1267	0.049*
C4	0.34281 (13)	0.0604 (2)	−0.11537 (7)	0.0397 (3)
C5	0.41168 (13)	0.1722 (2)	−0.06768 (7)	0.0415 (3)
H5	0.4694	0.2433	−0.0805	0.050*
C6	0.39447 (13)	0.1780 (2)	−0.00076 (7)	0.0408 (3)
C7	0.30000 (13)	0.0657 (2)	0.09607 (7)	0.0423 (4)
H7	0.3649	0.0498	0.1293	0.051*
C8	0.20325 (13)	0.0834 (2)	0.11704 (7)	0.0438 (4)
H8	0.1392	0.1032	0.0834	0.053*
C9	0.18682 (13)	0.0750 (2)	0.18830 (7)	0.0402 (3)
C10	0.27274 (13)	0.0222 (2)	0.24260 (7)	0.0414 (3)
H10	0.3437	−0.0082	0.2338	0.050*
C11	0.25443 (14)	0.0144 (2)	0.30867 (8)	0.0452 (4)
H11	0.3126	−0.0228	0.3440	0.054*
C12	0.14951 (15)	0.0617 (2)	0.32326 (8)	0.0482 (4)
C13	0.06376 (15)	0.1169 (3)	0.27093 (9)	0.0564 (4)
H13	−0.0063	0.1515	0.2802	0.068*
C14	0.08290 (14)	0.1205 (3)	0.20423 (8)	0.0532 (4)
H14	0.0240	0.1547	0.1689	0.064*
C15	0.0416 (2)	0.1174 (3)	0.41066 (10)	0.0789 (7)
H15A	0.0289	0.2479	0.3972	0.118*
H15B	0.0491	0.1069	0.4596	0.118*
H15C	−0.0212	0.0417	0.3887	0.118*
C16	0.36763 (14)	0.0499 (2)	−0.18629 (7)	0.0436 (4)
C17	0.30492 (19)	−0.0551 (3)	−0.29944 (8)	0.0643 (5)
H17A	0.3096	0.0684	−0.3194	0.096*
H17B	0.2435	−0.1248	−0.3262	0.096*
H17C	0.3743	−0.1227	−0.2989	0.096*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0415 (7)	0.1004 (11)	0.0674 (8)	−0.0141 (7)	0.0087 (6)	0.0031 (7)
O2	0.0759 (9)	0.0665 (8)	0.0517 (7)	−0.0140 (7)	0.0136 (6)	0.0150 (6)
O3	0.0460 (7)	0.0639 (8)	0.0697 (8)	−0.0054 (6)	0.0050 (6)	−0.0001 (6)
O4	0.1441 (16)	0.1327 (14)	0.0831 (10)	−0.0793 (13)	0.0717 (11)	−0.0634 (11)
O5	0.0556 (8)	0.0892 (9)	0.0480 (7)	−0.0032 (6)	0.0257 (6)	0.0026 (6)
O6	0.0704 (8)	0.0603 (7)	0.0318 (5)	−0.0085 (6)	0.0171 (5)	−0.0013 (5)
O7	0.0801 (10)	0.0965 (10)	0.0410 (6)	0.0177 (8)	0.0317 (6)	0.0101 (6)
N1	0.0461 (8)	0.0591 (8)	0.0358 (6)	−0.0084 (6)	0.0147 (5)	−0.0036 (6)
N2	0.0656 (9)	0.0539 (8)	0.0423 (7)	−0.0128 (7)	0.0153 (6)	−0.0020 (6)
C1	0.0380 (8)	0.0463 (8)	0.0328 (7)	0.0043 (6)	0.0108 (6)	0.0013 (6)
C2	0.0357 (7)	0.0467 (8)	0.0361 (7)	0.0011 (6)	0.0125 (6)	0.0032 (6)
C3	0.0411 (8)	0.0482 (8)	0.0329 (7)	0.0008 (6)	0.0093 (6)	−0.0001 (6)
C4	0.0445 (8)	0.0439 (8)	0.0334 (7)	0.0063 (6)	0.0137 (6)	0.0040 (6)
C5	0.0431 (8)	0.0443 (8)	0.0400 (7)	−0.0006 (6)	0.0155 (6)	0.0041 (6)
C6	0.0435 (8)	0.0435 (8)	0.0366 (7)	−0.0004 (6)	0.0105 (6)	−0.0001 (6)
C7	0.0417 (8)	0.0555 (9)	0.0301 (7)	−0.0022 (7)	0.0081 (6)	0.0004 (6)
C8	0.0403 (8)	0.0576 (9)	0.0335 (7)	0.0028 (7)	0.0071 (6)	−0.0006 (6)
C9	0.0426 (8)	0.0458 (8)	0.0342 (7)	−0.0020 (6)	0.0125 (6)	−0.0024 (6)
C10	0.0419 (8)	0.0466 (8)	0.0379 (7)	0.0021 (6)	0.0135 (6)	−0.0027 (6)
C11	0.0513 (9)	0.0488 (8)	0.0361 (7)	0.0025 (7)	0.0097 (6)	0.0028 (6)
C12	0.0603 (10)	0.0510 (9)	0.0386 (8)	0.0008 (8)	0.0230 (7)	0.0012 (6)
C13	0.0497 (10)	0.0754 (12)	0.0503 (9)	0.0077 (8)	0.0249 (8)	0.0014 (8)
C14	0.0435 (9)	0.0747 (11)	0.0428 (8)	0.0065 (8)	0.0118 (7)	0.0018 (8)
C15	0.1013 (17)	0.0906 (15)	0.0584 (11)	0.0216 (13)	0.0502 (11)	0.0071 (10)
C16	0.0519 (9)	0.0451 (8)	0.0371 (7)	0.0073 (7)	0.0167 (7)	0.0053 (6)
C17	0.1002 (16)	0.0639 (11)	0.0330 (8)	0.0023 (10)	0.0233 (9)	0.0006 (7)

Geometric parameters (Å, º) top

O1—N1	1.219 (2)	C7—C8	1.315 (2)
O2—N1	1.208 (2)	C7—H7	0.930
O3—N2	1.216 (2)	C8—C9	1.465 (2)
O4—N2	1.194 (2)	C8—H8	0.930
O5—C16	1.200 (2)	C9—C14	1.385 (2)
O6—C16	1.320 (2)	C9—C10	1.396 (2)
O6—C17	1.452 (2)	C10—C11	1.370 (2)
O7—C12	1.361 (2)	C10—H10	0.930
O7—C15	1.418 (2)	C11—C12	1.389 (2)
N1—C2	1.474 (2)	C11—H11	0.930
N2—C6	1.475 (2)	C12—C13	1.375 (3)
C1—C2	1.393 (2)	C13—C14	1.385 (2)
C1—C6	1.401 (2)	C13—H13	0.930
C1—C7	1.474 (2)	C14—H14	0.930
C2—C3	1.382 (2)	C15—H15A	0.960
C3—C4	1.386 (2)	C15—H15B	0.960
C3—H3	0.930	C15—H15C	0.960
C4—C5	1.380 (2)	C17—H17A	0.960
C4—C16	1.494 (2)	C17—H17B	0.960
C5—C6	1.382 (2)	C17—H17C	0.960
C5—H5	0.930

C16—O6—C17	115.7 (1)	C14—C9—C8	120.2 (1)
C12—O7—C15	118.4 (2)	C10—C9—C8	122.7 (1)
O2—N1—O1	125.0 (1)	C11—C10—C9	121.2 (1)
O2—N1—C2	118.3 (1)	C11—C10—H10	119.4
O1—N1—C2	116.7 (1)	C9—C10—H10	119.4
O4—N2—O3	123.3 (2)	C10—C11—C12	120.4 (2)
O4—N2—C6	118.9 (2)	C10—C11—H11	119.8
O3—N2—C6	117.7 (1)	C12—C11—H11	119.8
C2—C1—C6	113.5 (1)	O7—C12—C13	125.2 (2)
C2—C1—C7	122.8 (1)	O7—C12—C11	115.1 (2)
C6—C1—C7	123.7 (1)	C13—C12—C11	119.6 (1)
C3—C2—C1	124.7 (1)	C12—C13—C14	119.3 (2)
C3—C2—N1	115.6 (1)	C12—C13—H13	120.4
C1—C2—N1	119.5 (1)	C14—C13—H13	120.4
C2—C3—C4	118.9 (1)	C13—C14—C9	122.3 (2)
C2—C3—H3	120.6	C13—C14—H14	118.9
C4—C3—H3	120.6	C9—C14—H14	118.9
C5—C4—C3	119.3 (1)	O7—C15—H15A	109.5
C5—C4—C16	118.2 (1)	O7—C15—H15B	109.5
C3—C4—C16	122.4 (1)	H15A—C15—H15B	109.5
C4—C5—C6	119.7 (1)	O7—C15—H15C	109.5
C4—C5—H5	120.2	H15A—C15—H15C	109.5
C6—C5—H5	120.2	H15B—C15—H15C	109.5
C5—C6—C1	123.9 (1)	O5—C16—O6	125.0 (1)
C5—C6—N2	116.0 (1)	O5—C16—C4	122.7 (2)
C1—C6—N2	120.1 (1)	O6—C16—C4	112.2 (1)
C8—C7—C1	124.7 (1)	O6—C17—H17A	109.5
C8—C7—H7	117.6	O6—C17—H17B	109.5
C1—C7—H7	117.6	H17A—C17—H17B	109.5
C7—C8—C9	126.2 (1)	O6—C17—H17C	109.5
C7—C8—H8	116.9	H17A—C17—H17C	109.5
C9—C8—H8	116.9	H17B—C17—H17C	109.5
C14—C9—C10	117.2 (1)

C6—C1—C2—C3	−1.7 (2)	C2—C1—C7—C8	−50.5 (2)
C7—C1—C2—C3	−179.0 (1)	C6—C1—C7—C8	132.5 (2)
C6—C1—C2—N1	173.9 (1)	C1—C7—C8—C9	178.1 (1)
C7—C1—C2—N1	−3.5 (2)	C7—C8—C9—C14	171.5 (2)
O2—N1—C2—C3	118.0 (2)	C7—C8—C9—C10	−8.4 (3)
O1—N1—C2—C3	−60.4 (2)	C14—C9—C10—C11	0.6 (2)
O2—N1—C2—C1	−57.99 (19)	C8—C9—C10—C11	−179.5 (2)
O1—N1—C2—C1	123.7 (2)	C9—C10—C11—C12	−0.9 (2)
C1—C2—C3—C4	3.7 (2)	C15—O7—C12—C13	−5.5 (3)
N1—C2—C3—C4	−171.99 (13)	C15—O7—C12—C11	173.3 (2)
C2—C3—C4—C5	−2.3 (2)	C10—C11—C12—O7	−178.97 (15)
C2—C3—C4—C16	173.6 (1)	C10—C11—C12—C13	−0.1 (3)
C3—C4—C5—C6	−0.8 (2)	O7—C12—C13—C14	−179.89 (17)
C16—C4—C5—C6	−176.9 (1)	C11—C12—C13—C14	1.3 (3)
C4—C5—C6—C1	3.0 (2)	C12—C13—C14—C9	−1.7 (3)
C4—C5—C6—N2	−178.1 (1)	C10—C9—C14—C13	0.8 (3)
C2—C1—C6—C5	−1.7 (2)	C8—C9—C14—C13	−179.2 (2)
C7—C1—C6—C5	175.6 (1)	C17—O6—C16—O5	0.8 (2)
C2—C1—C6—N2	179.4 (1)	C17—O6—C16—C4	−178.3 (1)
C7—C1—C6—N2	−3.3 (2)	C5—C4—C16—O5	11.6 (2)
O4—N2—C6—C5	150.1 (2)	C3—C4—C16—O5	−164.4 (2)
O3—N2—C6—C5	−27.6 (2)	C5—C4—C16—O6	−169.3 (1)
O4—N2—C6—C1	−30.9 (2)	C3—C4—C16—O6	14.7 (2)
O3—N2—C6—C1	151.4 (1)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O1ⁱ	0.93	2.54	3.409 (2)	156
C17—H17A···O4ⁱⁱ	0.96	2.54	3.139 (3)	120

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

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Methyl 4-(4-methoxy­benzyl­idene­methyl)-3,5-di­nitro­benzoate

Supporting information

Key indicators

checkCIF/PLATON results

Methyl 4-(4-methoxybenzylidenemethyl)-3,5-dinitrobenzoate