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The title compound, C
17H
14N
2O
7, 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.
Supporting information
CCDC reference: 255912
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
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 |
Mr = 358.30 | Dx = 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 | Rint = 0.019 |
Graphite monochromator | θmax = 28.0°, θmin = 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(Fo2) + (0.0837P)2 + 0.21P] where P = (Fo2 + 2Fc2)/3 |
3785 reflections | (Δ/σ)max < 0.001 |
237 parameters | Δρmax = 0.28 e Å−3 |
0 restraints | Δρmin = −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 | Uiso*/Ueq | |
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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