



Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536808021077/rz2231sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536808021077/rz2231Isup2.hkl |
CCDC reference: 700504
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean
(C-C) = 0.002 Å
- R factor = 0.047
- wR factor = 0.138
- Data-to-parameter ratio = 15.9
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.96 PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 700 Deg.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 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 0 ALERT type 5 Informative message, check
The title compound was synthesized by the Wittig reaction. Triphenyl(p-nitrobenzyl)phosphonium chloride (0.01 mol), which was obtained by reacting 4-nitrobenzyl chlorine with triphenyl phosphine, and 3-nitrobenzaldehyde (0.01 mol) were dissolved in CH2Cl2 (15 ml), then a 50% NaOH solution (4 ml) was titrated into the mixture. The mixture was refluxed for 40 min at 45–50 °C. After cooling to room temperature, water (15 ml) was added and the mixture was extracted with ether (20 ml). The organic layer was washed with water and dried with anhydrous sodium sulfate, then it was filtered and concentrated. The resulting yellow solution was collected and purified by column chromatography on silica gel using petroleum ether and chloroform (10:1 v/v) as eluent (yield: 8.6%). Crystals of the title compound suitable for X-ray analysis were grown by slow evaporation of an ethanol solution. 1HNMR (CDCl3)(400 MHz; TMS p.p.m.), δ(p.p.m.): 6.83–6.90 (m, 2H, –C═C–), 7.31–7.54 (m, 4H, Ar), 8.13–8.17 (m, 4H, Ar).
The hydrogen atoms were generated geometrically and refined using a riding model, with C—H = 0.93 Å and Uiso(H) = 1.2 Ueq(C).
Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
C14H10N2O4 | Z = 2 |
Mr = 270.24 | F(000) = 280 |
Triclinic, P1 | Dx = 1.426 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.2995 (13) Å | Cell parameters from 1175 reflections |
b = 8.0561 (11) Å | θ = 3.5–27.2° |
c = 11.831 (2) Å | µ = 0.11 mm−1 |
α = 78.291 (7)° | T = 296 K |
β = 85.102 (7)° | Block, yellow |
γ = 67.536 (7)° | 0.50 × 0.24 × 0.19 mm |
V = 629.53 (18) Å3 |
Bruker SMART APEXII CCD diffractometer | 2902 independent reflections |
Radiation source: fine-focus sealed tube | 2009 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.021 |
ω scans | θmax = 27.9°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2002) | h = −9→9 |
Tmin = 0.946, Tmax = 0.981 | k = −10→9 |
4608 measured reflections | l = −15→15 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.047 | H-atom parameters constrained |
wR(F2) = 0.138 | w = 1/[σ2(Fo2) + (0.066P)2 + 0.0698P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
2902 reflections | Δρmax = 0.24 e Å−3 |
182 parameters | Δρmin = −0.19 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.036 (7) |
C14H10N2O4 | γ = 67.536 (7)° |
Mr = 270.24 | V = 629.53 (18) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.2995 (13) Å | Mo Kα radiation |
b = 8.0561 (11) Å | µ = 0.11 mm−1 |
c = 11.831 (2) Å | T = 296 K |
α = 78.291 (7)° | 0.50 × 0.24 × 0.19 mm |
β = 85.102 (7)° |
Bruker SMART APEXII CCD diffractometer | 2902 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2002) | 2009 reflections with I > 2σ(I) |
Tmin = 0.946, Tmax = 0.981 | Rint = 0.021 |
4608 measured reflections |
R[F2 > 2σ(F2)] = 0.047 | 0 restraints |
wR(F2) = 0.138 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.24 e Å−3 |
2902 reflections | Δρmin = −0.19 e Å−3 |
182 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C11 | 0.4027 (2) | 0.3521 (2) | 0.95493 (13) | 0.0408 (4) | |
C10 | 0.5246 (2) | 0.2712 (2) | 0.87050 (13) | 0.0407 (4) | |
H10A | 0.4941 | 0.3190 | 0.7930 | 0.049* | |
N2 | 0.2245 (2) | 0.51528 (19) | 0.92062 (12) | 0.0491 (4) | |
O4 | 0.1303 (2) | 0.59945 (18) | 0.99507 (11) | 0.0625 (4) | |
C9 | 0.6945 (2) | 0.1168 (2) | 0.90224 (13) | 0.0418 (4) | |
C14 | 0.7294 (3) | 0.0475 (2) | 1.01961 (14) | 0.0491 (4) | |
H14A | 0.8396 | −0.0581 | 1.0424 | 0.059* | |
C4 | 0.8254 (2) | 0.2702 (2) | 0.64805 (13) | 0.0445 (4) | |
C1 | 0.7410 (2) | 0.6180 (2) | 0.52136 (13) | 0.0437 (4) | |
N1 | 0.7019 (2) | 0.8008 (2) | 0.45317 (13) | 0.0553 (4) | |
C12 | 0.4397 (3) | 0.2862 (2) | 1.07097 (14) | 0.0509 (4) | |
H12A | 0.3552 | 0.3448 | 1.1262 | 0.061* | |
O2 | 0.7283 (2) | 0.91400 (19) | 0.49721 (13) | 0.0734 (4) | |
O3 | 0.1784 (2) | 0.5610 (2) | 0.81952 (12) | 0.0804 (5) | |
C3 | 0.8289 (3) | 0.4109 (2) | 0.69887 (14) | 0.0518 (4) | |
H3A | 0.8598 | 0.3868 | 0.7767 | 0.062* | |
C6 | 0.7387 (3) | 0.4823 (2) | 0.46765 (14) | 0.0490 (4) | |
H6A | 0.7089 | 0.5071 | 0.3896 | 0.059* | |
C5 | 0.7812 (2) | 0.3098 (2) | 0.53140 (14) | 0.0485 (4) | |
H5A | 0.7803 | 0.2174 | 0.4957 | 0.058* | |
C2 | 0.7876 (3) | 0.5846 (2) | 0.63620 (14) | 0.0509 (4) | |
H2A | 0.7911 | 0.6773 | 0.6707 | 0.061* | |
C13 | 0.6048 (3) | 0.1315 (3) | 1.10274 (14) | 0.0547 (5) | |
H13A | 0.6326 | 0.0834 | 1.1805 | 0.066* | |
C8 | 0.8307 (3) | 0.0184 (2) | 0.81795 (15) | 0.0511 (4) | |
H8A | 0.8927 | −0.1070 | 0.8429 | 0.061* | |
C7 | 0.8788 (3) | 0.0810 (2) | 0.71159 (15) | 0.0531 (4) | |
H7A | 0.9588 | −0.0085 | 0.6709 | 0.064* | |
O1 | 0.6446 (3) | 0.8324 (2) | 0.35477 (12) | 0.0854 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C11 | 0.0452 (9) | 0.0352 (8) | 0.0444 (8) | −0.0183 (7) | 0.0008 (6) | −0.0066 (6) |
C10 | 0.0452 (8) | 0.0378 (8) | 0.0383 (7) | −0.0167 (7) | −0.0026 (6) | −0.0025 (6) |
N2 | 0.0481 (8) | 0.0430 (8) | 0.0556 (8) | −0.0150 (6) | 0.0023 (6) | −0.0129 (7) |
O4 | 0.0606 (8) | 0.0543 (8) | 0.0711 (8) | −0.0164 (6) | 0.0168 (6) | −0.0256 (6) |
C9 | 0.0439 (9) | 0.0350 (8) | 0.0457 (8) | −0.0163 (7) | −0.0029 (6) | −0.0018 (6) |
C14 | 0.0525 (10) | 0.0419 (9) | 0.0503 (9) | −0.0207 (8) | −0.0091 (7) | 0.0066 (7) |
C4 | 0.0398 (8) | 0.0452 (9) | 0.0452 (8) | −0.0129 (7) | 0.0074 (6) | −0.0104 (7) |
C1 | 0.0399 (8) | 0.0440 (9) | 0.0449 (8) | −0.0156 (7) | 0.0068 (6) | −0.0060 (7) |
N1 | 0.0540 (9) | 0.0489 (9) | 0.0581 (9) | −0.0181 (7) | 0.0067 (7) | −0.0047 (7) |
C12 | 0.0675 (11) | 0.0484 (10) | 0.0420 (8) | −0.0291 (9) | 0.0087 (8) | −0.0086 (7) |
O2 | 0.0851 (11) | 0.0496 (8) | 0.0885 (10) | −0.0295 (7) | 0.0047 (8) | −0.0130 (7) |
O3 | 0.0746 (10) | 0.0741 (10) | 0.0590 (8) | 0.0134 (8) | −0.0155 (7) | −0.0145 (7) |
C3 | 0.0642 (11) | 0.0569 (11) | 0.0373 (8) | −0.0261 (9) | 0.0041 (7) | −0.0105 (7) |
C6 | 0.0498 (10) | 0.0544 (10) | 0.0416 (8) | −0.0181 (8) | −0.0002 (7) | −0.0095 (7) |
C5 | 0.0512 (10) | 0.0495 (10) | 0.0476 (9) | −0.0185 (8) | 0.0046 (7) | −0.0180 (7) |
C2 | 0.0624 (11) | 0.0497 (10) | 0.0462 (9) | −0.0260 (8) | 0.0092 (7) | −0.0157 (7) |
C13 | 0.0726 (12) | 0.0543 (10) | 0.0384 (8) | −0.0311 (9) | −0.0056 (8) | 0.0053 (7) |
C8 | 0.0503 (10) | 0.0353 (8) | 0.0586 (10) | −0.0082 (7) | −0.0026 (8) | −0.0035 (7) |
C7 | 0.0526 (10) | 0.0427 (9) | 0.0556 (10) | −0.0085 (8) | 0.0078 (8) | −0.0129 (8) |
O1 | 0.1193 (14) | 0.0700 (10) | 0.0582 (9) | −0.0343 (9) | −0.0165 (8) | 0.0116 (7) |
C11—C10 | 1.372 (2) | C1—N1 | 1.462 (2) |
C11—C12 | 1.377 (2) | N1—O1 | 1.2150 (19) |
C11—N2 | 1.467 (2) | N1—O2 | 1.218 (2) |
C10—C9 | 1.392 (2) | C12—C13 | 1.374 (3) |
C10—H10A | 0.9300 | C12—H12A | 0.9300 |
N2—O3 | 1.2143 (18) | C3—C2 | 1.376 (2) |
N2—O4 | 1.2209 (17) | C3—H3A | 0.9300 |
C9—C14 | 1.393 (2) | C6—C5 | 1.371 (2) |
C9—C8 | 1.470 (2) | C6—H6A | 0.9300 |
C14—C13 | 1.378 (3) | C5—H5A | 0.9300 |
C14—H14A | 0.9300 | C2—H2A | 0.9300 |
C4—C5 | 1.389 (2) | C13—H13A | 0.9300 |
C4—C3 | 1.397 (2) | C8—C7 | 1.328 (2) |
C4—C7 | 1.473 (2) | C8—H8A | 0.9300 |
C1—C2 | 1.376 (2) | C7—H7A | 0.9300 |
C1—C6 | 1.378 (2) | ||
C10—C11—C12 | 122.86 (15) | C13—C12—C11 | 118.13 (16) |
C10—C11—N2 | 118.83 (13) | C13—C12—H12A | 120.9 |
C12—C11—N2 | 118.31 (15) | C11—C12—H12A | 120.9 |
C11—C10—C9 | 119.22 (14) | C2—C3—C4 | 121.34 (15) |
C11—C10—H10A | 120.4 | C2—C3—H3A | 119.3 |
C9—C10—H10A | 120.4 | C4—C3—H3A | 119.3 |
O3—N2—O4 | 123.14 (15) | C5—C6—C1 | 118.73 (15) |
O3—N2—C11 | 118.50 (14) | C5—C6—H6A | 120.6 |
O4—N2—C11 | 118.35 (14) | C1—C6—H6A | 120.6 |
C10—C9—C14 | 117.92 (15) | C6—C5—C4 | 121.50 (15) |
C10—C9—C8 | 122.99 (14) | C6—C5—H5A | 119.2 |
C14—C9—C8 | 118.99 (15) | C4—C5—H5A | 119.2 |
C13—C14—C9 | 121.71 (16) | C3—C2—C1 | 118.52 (16) |
C13—C14—H14A | 119.1 | C3—C2—H2A | 120.7 |
C9—C14—H14A | 119.1 | C1—C2—H2A | 120.7 |
C5—C4—C3 | 117.99 (15) | C12—C13—C14 | 120.13 (15) |
C5—C4—C7 | 119.46 (15) | C12—C13—H13A | 119.9 |
C3—C4—C7 | 122.43 (15) | C14—C13—H13A | 119.9 |
C2—C1—C6 | 121.91 (15) | C7—C8—C9 | 129.92 (15) |
C2—C1—N1 | 119.00 (15) | C7—C8—H8A | 115.0 |
C6—C1—N1 | 119.03 (15) | C9—C8—H8A | 115.0 |
O1—N1—O2 | 123.13 (16) | C8—C7—C4 | 130.11 (16) |
O1—N1—C1 | 118.13 (16) | C8—C7—H7A | 114.9 |
O2—N1—C1 | 118.75 (15) | C4—C7—H7A | 114.9 |
C12—C11—C10—C9 | −0.7 (2) | C7—C4—C3—C2 | 176.81 (16) |
N2—C11—C10—C9 | 179.75 (13) | C2—C1—C6—C5 | 1.0 (3) |
C10—C11—N2—O3 | 8.4 (2) | N1—C1—C6—C5 | 178.16 (14) |
C12—C11—N2—O3 | −171.23 (16) | C1—C6—C5—C4 | 0.2 (3) |
C10—C11—N2—O4 | −171.07 (14) | C3—C4—C5—C6 | −1.1 (2) |
C12—C11—N2—O4 | 9.3 (2) | C7—C4—C5—C6 | −177.24 (16) |
C11—C10—C9—C14 | 2.1 (2) | C4—C3—C2—C1 | 0.4 (3) |
C11—C10—C9—C8 | 178.34 (14) | C6—C1—C2—C3 | −1.3 (3) |
C10—C9—C14—C13 | −2.3 (2) | N1—C1—C2—C3 | −178.45 (16) |
C8—C9—C14—C13 | −178.65 (16) | C11—C12—C13—C14 | 0.6 (3) |
C2—C1—N1—O1 | −173.84 (17) | C9—C14—C13—C12 | 0.9 (3) |
C6—C1—N1—O1 | 8.9 (2) | C10—C9—C8—C7 | 32.4 (3) |
C2—C1—N1—O2 | 6.3 (2) | C14—C9—C8—C7 | −151.46 (19) |
C6—C1—N1—O2 | −170.93 (15) | C9—C8—C7—C4 | 6.1 (3) |
C10—C11—C12—C13 | −0.8 (3) | C5—C4—C7—C8 | −140.7 (2) |
N2—C11—C12—C13 | 178.83 (14) | C3—C4—C7—C8 | 43.3 (3) |
C5—C4—C3—C2 | 0.8 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C13—H13A···O1i | 0.93 | 2.56 | 3.388 (2) | 149 |
Symmetry code: (i) x, y−1, z+1. |
Experimental details
Crystal data | |
Chemical formula | C14H10N2O4 |
Mr | 270.24 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 296 |
a, b, c (Å) | 7.2995 (13), 8.0561 (11), 11.831 (2) |
α, β, γ (°) | 78.291 (7), 85.102 (7), 67.536 (7) |
V (Å3) | 629.53 (18) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.11 |
Crystal size (mm) | 0.50 × 0.24 × 0.19 |
Data collection | |
Diffractometer | Bruker SMART APEXII CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2002) |
Tmin, Tmax | 0.946, 0.981 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4608, 2902, 2009 |
Rint | 0.021 |
(sin θ/λ)max (Å−1) | 0.658 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.138, 1.03 |
No. of reflections | 2902 |
No. of parameters | 182 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.24, −0.19 |
Computer programs: SMART (Bruker, 2003), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
C13—H13A···O1i | 0.93 | 2.56 | 3.388 (2) | 148.6 |
Symmetry code: (i) x, y−1, z+1. |
Recently, stilbene derivatives have attracted considerable attention from chemists and biologists because of their non-linear optical properties (Soto Bustmante et al., 1995; Papper & Likhtenshtein, 2001) and biological activities (Boonlaksiri et al., 2000). The crystal structure of the related isomer (Z)-1,2-bis(4-nitrophenyl)ethene has been previously reported by our group (Chen & Cao, 2007). We report here the crystal structure of the title compound (Fig. 1), a cis-stilbene derivative.
In the title compound, the C4—C7—C8 and C9—C8—C7 bond angles are 130.11 (16) and 129.92 (15)°, respectively. They are larger than the idealized value of 120° expected for sp2 hybrid orbitals due to the comparatively strong stereo hindrance between the two aryl groups. The dihedral angle between the two benzene rings is 53.66 (5)°. The nitro groups at C1 and C11 are slightly twisted out of the plane of the attached benzene rings forming dihedral angles of 7.92 (14) and 9.22 (10)°, respectively. In the crystal structure (Fig. 2), there is non-classical intermolecular C—H···O hydrogen bond (Table 1) linking molecules into chains running parallel to the [0 -1 1] direction.