Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807040202/lh2441sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807040202/lh2441Isup2.hkl |
CCDC reference: 663729
Key indicators
- Single-crystal X-ray study
- T = 291 K
- Mean (C-C) = 0.003 Å
- R factor = 0.046
- wR factor = 0.135
- Data-to-parameter ratio = 12.0
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 200 Deg. PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N1 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N2 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N3
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 48
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 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
6,6'-Dimethoxy-2,2'-dinitro-1,1'-biphenyl was prepared according to the reported procedure (Chen et al., 2001). The title compound was synthesized by the nitration reaction of 6,6'-Dimethoxy-2,2'-dinitro-1,1'-biphenyl (0.5 mmol) in 20 ml fuming nitric acid at room temperature for 24 h. The resulting solution was poured into 50 ml ice water and the precipitation was collected by filtration and recrystallized from ethyl acetate as single crystals of the title compound, which were suitable for X-ray diffraction analysis.
All H atoms were placed in calculated positions with C—H distances 0.93–0.96 Å and included in the refinement in the riding-model approximation with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(C) for methyl H atoms. Atoms O2—O9 were loosely restrained to be approximately isotropic.
Nitro compounds, specifically aromatic nitro compounds have been widely studied owing to their potential application in e.g. pathology (Ramkishen et al., 2005), materials science (Shinichi & Yuichiro, 2005) and powder technology (Zhang, 2006). These compounds can also be reduced to obtain hydroxylamine, azo-, azoxy compounds and amines, which find applications in dyes, agrochemicals, pharmaceuticals and photographic chemicals (Agrawal & Tratnyek, 1996). In this paper, we report the synthesis and crystal structure of the title compound.
All bond lengths and angles in the title molecule (Fig. 1) are in the expected range (Unver et al., 2002) and in good agreement with those reported previously (Yang et al., 2005). Atoms N1/N2/O1/C1—C6/C14 lie in a plane with the largest deviation being 0.029 Å for atom N2, and atoms N3/N4/O10/C7—C12 also lie in a plane, with the largest deviation being 0.0354 Å for atom N4. The dihedral angle between the two benzene rings is 90.1°, which is considerably larger than found in other biphenyls (Fischer et al., 2007), possibly due to the concomitant effects of steric hindrance of the methoxy and nitro groups. The dihedral angles formed between the benzene ring of C1—C6 and planes N1/O2/O3 and N2/O4/O5 are 24.3 and 70.4°, the dihedral angles formed between the benzene ring of C7—C12 and planes N3/O6/O7 and N4/O8/O9 are 15.7 and 43.0°, respectively. The H atom of the methoxy group forms weak C—H···O intermolecular hydrogen bonds with the nitro group O atom of the neighbouring molecule. The H13B···O5i distance is 2.41 Å, which is considerable shorter than the sum of the van der Waals radii for O and H (2.70 Å). In the crystal structure, molecules are connected to form a one-dimension chain via weak C—H···O hydrogen bonds. In addition, there are also weak C—H···O hydrogen bonds between two one-dimension chains (Fig.2). The H14A···O6ii distance is 2.60 Å. These weak intermolecular C—H···O hydrogen bonds play an important role in stabilizing the crystal structure (symmetry operation: (i) 1 + x,y,z; (ii) 1 - x,1 - y,1 - z).
For related literature, see: Agrawal & Tratnyek (1996); Fischer et al. (2007); Chen et al. (2001); Ramkishen et al. (2005); Shinichi & Yuichiro (2005); Unver et al. (2002); Yang et al. (2005); Zhang (2006).
Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2004); software used to prepare material for publication: SHELXTL (Bruker, 2004).
Fig. 1. The molecular structure of the title compound shown using 30% probability ellipsoids. | |
Fig. 2. Part of the title crystal structure with hydrogen bonds shown as dashed lines |
C14H10N4O10 | Z = 2 |
Mr = 394.26 | F(000) = 404 |
Triclinic, P1 | Dx = 1.589 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.1821 (11) Å | Cell parameters from 1810 reflections |
b = 10.2161 (13) Å | θ = 2.7–23.5° |
c = 10.6133 (14) Å | µ = 0.14 mm−1 |
α = 95.118 (2)° | T = 291 K |
β = 90.579 (2)° | Block, yellow |
γ = 110.977 (2)° | 0.27 × 0.23 × 0.16 mm |
V = 824.21 (19) Å3 |
Bruker APEX II CCD area-detector diffractometer | 3051 independent reflections |
Radiation source: fine-focus sealed tube | 2173 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.017 |
φ and ω scans | θmax = 25.5°, θmin = 2.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −9→9 |
Tmin = 0.913, Tmax = 0.979 | k = −12→12 |
6347 measured reflections | l = −12→12 |
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) = 0.135 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.06P)2 + 0.3203P] where P = (Fo2 + 2Fc2)/3 |
3051 reflections | (Δ/σ)max < 0.001 |
255 parameters | Δρmax = 0.27 e Å−3 |
48 restraints | Δρmin = −0.22 e Å−3 |
C14H10N4O10 | γ = 110.977 (2)° |
Mr = 394.26 | V = 824.21 (19) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.1821 (11) Å | Mo Kα radiation |
b = 10.2161 (13) Å | µ = 0.14 mm−1 |
c = 10.6133 (14) Å | T = 291 K |
α = 95.118 (2)° | 0.27 × 0.23 × 0.16 mm |
β = 90.579 (2)° |
Bruker APEX II CCD area-detector diffractometer | 3051 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2173 reflections with I > 2σ(I) |
Tmin = 0.913, Tmax = 0.979 | Rint = 0.017 |
6347 measured reflections |
R[F2 > 2σ(F2)] = 0.046 | 48 restraints |
wR(F2) = 0.135 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.27 e Å−3 |
3051 reflections | Δρmin = −0.22 e Å−3 |
255 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 | ||
O1 | 0.5521 (2) | 0.38404 (17) | 0.32635 (15) | 0.0544 (5) | |
O2 | 0.1047 (4) | −0.2166 (3) | 0.4665 (3) | 0.1216 (11) | |
O3 | −0.0829 (3) | −0.1796 (2) | 0.3485 (2) | 0.0847 (7) | |
O4 | 0.0530 (3) | −0.1066 (2) | 0.1089 (2) | 0.0836 (7) | |
O5 | −0.0687 (3) | 0.0425 (2) | 0.1627 (3) | 0.0909 (8) | |
O6 | 0.1341 (3) | 0.3722 (2) | 0.32138 (19) | 0.0735 (6) | |
O7 | 0.0125 (3) | 0.4502 (3) | 0.1823 (2) | 0.0864 (7) | |
O8 | 0.5697 (3) | 0.3399 (2) | −0.2476 (2) | 0.0972 (8) | |
O9 | 0.4681 (3) | 0.1229 (2) | −0.2111 (2) | 0.0861 (7) | |
O10 | 0.4716 (2) | 0.13198 (17) | 0.05720 (16) | 0.0505 (4) | |
N1 | 0.0619 (3) | −0.1446 (2) | 0.3991 (2) | 0.0620 (6) | |
N2 | 0.0430 (3) | −0.0071 (2) | 0.1743 (2) | 0.0520 (5) | |
N3 | 0.1122 (3) | 0.3936 (2) | 0.2140 (2) | 0.0504 (5) | |
N4 | 0.4869 (3) | 0.2450 (3) | −0.1846 (2) | 0.0614 (6) | |
C1 | 0.4371 (3) | 0.2571 (2) | 0.3497 (2) | 0.0416 (5) | |
C2 | 0.4469 (3) | 0.1889 (3) | 0.4556 (2) | 0.0502 (6) | |
H2 | 0.5365 | 0.2319 | 0.5171 | 0.060* | |
C3 | 0.3246 (3) | 0.0579 (3) | 0.4698 (2) | 0.0522 (6) | |
H3 | 0.3322 | 0.0127 | 0.5407 | 0.063* | |
C4 | 0.1917 (3) | −0.0063 (2) | 0.3801 (2) | 0.0446 (6) | |
C5 | 0.1809 (3) | 0.0619 (2) | 0.2745 (2) | 0.0384 (5) | |
C6 | 0.3011 (3) | 0.1926 (2) | 0.25653 (19) | 0.0364 (5) | |
C7 | 0.2998 (3) | 0.2600 (2) | 0.13651 (19) | 0.0357 (5) | |
C8 | 0.2142 (3) | 0.3520 (2) | 0.1146 (2) | 0.0406 (5) | |
C9 | 0.2197 (3) | 0.4097 (3) | 0.0016 (2) | 0.0488 (6) | |
H9 | 0.1601 | 0.4704 | −0.0098 | 0.059* | |
C10 | 0.3139 (3) | 0.3768 (3) | −0.0940 (2) | 0.0520 (7) | |
H10 | 0.3219 | 0.4173 | −0.1699 | 0.062* | |
C11 | 0.3963 (3) | 0.2837 (2) | −0.0768 (2) | 0.0443 (6) | |
C12 | 0.3931 (3) | 0.2246 (2) | 0.0373 (2) | 0.0395 (5) | |
C13 | 0.6577 (4) | 0.1862 (3) | 0.0691 (4) | 0.0756 (9) | |
H13A | 0.7046 | 0.2154 | −0.0106 | 0.113* | |
H13B | 0.6981 | 0.1144 | 0.0936 | 0.113* | |
H13C | 0.6961 | 0.2655 | 0.1323 | 0.113* | |
C14 | 0.6954 (4) | 0.4544 (3) | 0.4180 (3) | 0.0752 (9) | |
H14A | 0.6497 | 0.4677 | 0.4991 | 0.113* | |
H14B | 0.7652 | 0.5443 | 0.3916 | 0.113* | |
H14C | 0.7665 | 0.3979 | 0.4240 | 0.113* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0564 (11) | 0.0439 (9) | 0.0475 (10) | −0.0004 (8) | −0.0195 (8) | 0.0068 (8) |
O2 | 0.113 (2) | 0.0900 (17) | 0.145 (2) | 0.0020 (15) | −0.0259 (18) | 0.0791 (18) |
O3 | 0.0612 (14) | 0.0777 (15) | 0.0961 (17) | −0.0033 (11) | −0.0029 (12) | 0.0326 (12) |
O4 | 0.0737 (14) | 0.0805 (15) | 0.0690 (13) | 0.0022 (12) | −0.0046 (11) | −0.0245 (12) |
O5 | 0.0572 (13) | 0.0830 (15) | 0.129 (2) | 0.0206 (12) | −0.0363 (13) | 0.0153 (14) |
O6 | 0.0964 (16) | 0.0887 (15) | 0.0536 (12) | 0.0538 (13) | 0.0126 (11) | 0.0124 (11) |
O7 | 0.0846 (15) | 0.1112 (18) | 0.0920 (16) | 0.0701 (15) | −0.0017 (12) | 0.0103 (13) |
O8 | 0.121 (2) | 0.0786 (15) | 0.0592 (13) | −0.0054 (14) | 0.0337 (13) | 0.0081 (11) |
O9 | 0.1195 (19) | 0.0698 (15) | 0.0668 (14) | 0.0321 (14) | 0.0249 (13) | 0.0010 (11) |
O10 | 0.0510 (10) | 0.0455 (9) | 0.0585 (11) | 0.0205 (8) | 0.0040 (8) | 0.0098 (8) |
N1 | 0.0672 (16) | 0.0547 (14) | 0.0580 (14) | 0.0099 (12) | 0.0050 (12) | 0.0258 (11) |
N2 | 0.0424 (12) | 0.0499 (13) | 0.0513 (13) | −0.0002 (10) | −0.0059 (10) | 0.0142 (11) |
N3 | 0.0488 (12) | 0.0467 (12) | 0.0558 (14) | 0.0186 (10) | −0.0047 (10) | 0.0013 (10) |
N4 | 0.0704 (15) | 0.0580 (15) | 0.0388 (12) | 0.0036 (12) | 0.0053 (11) | 0.0002 (11) |
C1 | 0.0446 (13) | 0.0403 (12) | 0.0367 (12) | 0.0116 (11) | −0.0051 (10) | 0.0035 (10) |
C2 | 0.0561 (15) | 0.0540 (15) | 0.0357 (13) | 0.0148 (12) | −0.0126 (11) | 0.0036 (11) |
C3 | 0.0621 (16) | 0.0576 (16) | 0.0389 (13) | 0.0216 (13) | −0.0024 (12) | 0.0160 (11) |
C4 | 0.0464 (13) | 0.0432 (13) | 0.0424 (13) | 0.0120 (11) | 0.0045 (10) | 0.0125 (10) |
C5 | 0.0385 (12) | 0.0400 (12) | 0.0364 (12) | 0.0135 (10) | −0.0017 (9) | 0.0049 (9) |
C6 | 0.0381 (12) | 0.0378 (12) | 0.0325 (11) | 0.0125 (10) | −0.0026 (9) | 0.0047 (9) |
C7 | 0.0355 (11) | 0.0323 (11) | 0.0336 (11) | 0.0054 (9) | −0.0077 (9) | 0.0037 (9) |
C8 | 0.0371 (12) | 0.0367 (12) | 0.0429 (13) | 0.0078 (10) | −0.0081 (10) | 0.0022 (10) |
C9 | 0.0527 (14) | 0.0418 (13) | 0.0497 (14) | 0.0135 (11) | −0.0148 (12) | 0.0105 (11) |
C10 | 0.0598 (16) | 0.0449 (14) | 0.0420 (14) | 0.0057 (12) | −0.0136 (12) | 0.0145 (11) |
C11 | 0.0472 (13) | 0.0402 (12) | 0.0342 (12) | 0.0026 (11) | −0.0021 (10) | 0.0014 (10) |
C12 | 0.0400 (12) | 0.0328 (11) | 0.0399 (12) | 0.0064 (10) | −0.0057 (10) | 0.0039 (9) |
C13 | 0.0544 (17) | 0.0631 (18) | 0.110 (3) | 0.0250 (15) | −0.0126 (16) | −0.0002 (17) |
C14 | 0.0695 (19) | 0.0616 (18) | 0.0679 (19) | −0.0081 (15) | −0.0308 (15) | 0.0075 (15) |
O1—C1 | 1.348 (3) | C3—C4 | 1.370 (3) |
O1—C14 | 1.444 (3) | C3—H3 | 0.9300 |
O2—N1 | 1.203 (3) | C4—C5 | 1.389 (3) |
O3—N1 | 1.212 (3) | C5—C6 | 1.377 (3) |
O4—N2 | 1.206 (3) | C6—C7 | 1.503 (3) |
O5—N2 | 1.204 (3) | C7—C8 | 1.391 (3) |
O6—N3 | 1.203 (3) | C7—C12 | 1.402 (3) |
O7—N3 | 1.216 (3) | C8—C9 | 1.377 (3) |
O8—N4 | 1.225 (3) | C9—C10 | 1.370 (4) |
O9—N4 | 1.208 (3) | C9—H9 | 0.9300 |
O10—C12 | 1.349 (3) | C10—C11 | 1.371 (3) |
O10—C13 | 1.422 (3) | C10—H10 | 0.9300 |
N1—C4 | 1.465 (3) | C11—C12 | 1.397 (3) |
N2—C5 | 1.474 (3) | C13—H13A | 0.9600 |
N3—C8 | 1.478 (3) | C13—H13B | 0.9600 |
N4—C11 | 1.471 (3) | C13—H13C | 0.9600 |
C1—C2 | 1.391 (3) | C14—H14A | 0.9600 |
C1—C6 | 1.410 (3) | C14—H14B | 0.9600 |
C2—C3 | 1.376 (4) | C14—H14C | 0.9600 |
C2—H2 | 0.9300 | ||
C1—O1—C14 | 117.70 (19) | C1—C6—C7 | 120.03 (19) |
C12—O10—C13 | 116.79 (19) | C8—C7—C12 | 117.51 (19) |
O2—N1—O3 | 123.6 (2) | C8—C7—C6 | 126.4 (2) |
O2—N1—C4 | 117.7 (2) | C12—C7—C6 | 116.11 (19) |
O3—N1—C4 | 118.7 (2) | C9—C8—C7 | 122.9 (2) |
O5—N2—O4 | 125.2 (2) | C9—C8—N3 | 116.4 (2) |
O5—N2—C5 | 117.1 (2) | C7—C8—N3 | 120.8 (2) |
O4—N2—C5 | 117.7 (2) | C10—C9—C8 | 119.3 (2) |
O6—N3—O7 | 123.7 (2) | C10—C9—H9 | 120.4 |
O6—N3—C8 | 118.7 (2) | C8—C9—H9 | 120.4 |
O7—N3—C8 | 117.6 (2) | C9—C10—C11 | 119.4 (2) |
O9—N4—O8 | 123.6 (2) | C9—C10—H10 | 120.3 |
O9—N4—C11 | 119.4 (2) | C11—C10—H10 | 120.3 |
O8—N4—C11 | 116.8 (2) | C10—C11—C12 | 122.2 (2) |
O1—C1—C2 | 124.6 (2) | C10—C11—N4 | 117.5 (2) |
O1—C1—C6 | 115.30 (19) | C12—C11—N4 | 120.4 (2) |
C2—C1—C6 | 120.1 (2) | O10—C12—C11 | 123.7 (2) |
C3—C2—C1 | 120.3 (2) | O10—C12—C7 | 117.54 (19) |
C3—C2—H2 | 119.9 | C11—C12—C7 | 118.7 (2) |
C1—C2—H2 | 119.9 | O10—C13—H13A | 109.5 |
C4—C3—C2 | 120.4 (2) | O10—C13—H13B | 109.5 |
C4—C3—H3 | 119.8 | H13A—C13—H13B | 109.5 |
C2—C3—H3 | 119.8 | O10—C13—H13C | 109.5 |
C3—C4—C5 | 119.5 (2) | H13A—C13—H13C | 109.5 |
C3—C4—N1 | 119.0 (2) | H13B—C13—H13C | 109.5 |
C5—C4—N1 | 121.5 (2) | O1—C14—H14A | 109.5 |
C6—C5—C4 | 121.9 (2) | O1—C14—H14B | 109.5 |
C6—C5—N2 | 117.51 (18) | H14A—C14—H14B | 109.5 |
C4—C5—N2 | 120.5 (2) | O1—C14—H14C | 109.5 |
C5—C6—C1 | 117.90 (19) | H14A—C14—H14C | 109.5 |
C5—C6—C7 | 121.83 (18) | H14B—C14—H14C | 109.5 |
C14—O1—C1—C2 | −0.1 (4) | C5—C6—C7—C12 | −86.7 (3) |
C14—O1—C1—C6 | −179.3 (2) | C1—C6—C7—C12 | 87.5 (3) |
O1—C1—C2—C3 | −178.8 (2) | C12—C7—C8—C9 | −0.9 (3) |
C6—C1—C2—C3 | 0.3 (4) | C6—C7—C8—C9 | 179.9 (2) |
C1—C2—C3—C4 | −0.3 (4) | C12—C7—C8—N3 | 179.59 (18) |
C2—C3—C4—C5 | −0.1 (4) | C6—C7—C8—N3 | 0.3 (3) |
C2—C3—C4—N1 | −178.9 (2) | O6—N3—C8—C9 | −163.8 (2) |
O2—N1—C4—C3 | −24.1 (4) | O7—N3—C8—C9 | 14.9 (3) |
O3—N1—C4—C3 | 154.7 (3) | O6—N3—C8—C7 | 15.8 (3) |
O2—N1—C4—C5 | 157.1 (3) | O7—N3—C8—C7 | −165.5 (2) |
O3—N1—C4—C5 | −24.1 (4) | C7—C8—C9—C10 | −0.4 (3) |
C3—C4—C5—C6 | 0.5 (4) | N3—C8—C9—C10 | 179.2 (2) |
N1—C4—C5—C6 | 179.3 (2) | C8—C9—C10—C11 | 2.0 (3) |
C3—C4—C5—N2 | 177.7 (2) | C9—C10—C11—C12 | −2.4 (3) |
N1—C4—C5—N2 | −3.5 (4) | C9—C10—C11—N4 | 176.4 (2) |
O5—N2—C5—C6 | −70.8 (3) | O9—N4—C11—C10 | −134.9 (3) |
O4—N2—C5—C6 | 107.7 (3) | O8—N4—C11—C10 | 40.7 (3) |
O5—N2—C5—C4 | 111.9 (3) | O9—N4—C11—C12 | 43.9 (3) |
O4—N2—C5—C4 | −69.7 (3) | O8—N4—C11—C12 | −140.5 (3) |
C4—C5—C6—C1 | −0.4 (3) | C13—O10—C12—C11 | 72.0 (3) |
N2—C5—C6—C1 | −177.7 (2) | C13—O10—C12—C7 | −109.6 (3) |
C4—C5—C6—C7 | 173.9 (2) | C10—C11—C12—O10 | 179.5 (2) |
N2—C5—C6—C7 | −3.5 (3) | N4—C11—C12—O10 | 0.7 (3) |
O1—C1—C6—C5 | 179.2 (2) | C10—C11—C12—C7 | 1.2 (3) |
C2—C1—C6—C5 | 0.0 (3) | N4—C11—C12—C7 | −177.63 (19) |
O1—C1—C6—C7 | 4.8 (3) | C8—C7—C12—O10 | −177.95 (18) |
C2—C1—C6—C7 | −174.4 (2) | C6—C7—C12—O10 | 1.4 (3) |
C5—C6—C7—C8 | 92.6 (3) | C8—C7—C12—C11 | 0.5 (3) |
C1—C6—C7—C8 | −93.3 (3) | C6—C7—C12—C11 | 179.82 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
C13—H13B···O5i | 0.96 | 2.41 | 3.274 (4) | 150 |
C14—H14A···O6ii | 0.96 | 2.60 | 3.165 (3) | 118 |
Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C14H10N4O10 |
Mr | 394.26 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 291 |
a, b, c (Å) | 8.1821 (11), 10.2161 (13), 10.6133 (14) |
α, β, γ (°) | 95.118 (2), 90.579 (2), 110.977 (2) |
V (Å3) | 824.21 (19) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.14 |
Crystal size (mm) | 0.27 × 0.23 × 0.16 |
Data collection | |
Diffractometer | Bruker APEX II CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.913, 0.979 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6347, 3051, 2173 |
Rint | 0.017 |
(sin θ/λ)max (Å−1) | 0.606 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.046, 0.135, 1.04 |
No. of reflections | 3051 |
No. of parameters | 255 |
No. of restraints | 48 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.27, −0.22 |
Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2004).
D—H···A | D—H | H···A | D···A | D—H···A |
C13—H13B···O5i | 0.96 | 2.41 | 3.274 (4) | 150.3 |
C14—H14A···O6ii | 0.96 | 2.60 | 3.165 (3) | 118.2 |
Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y+1, −z+1. |
Nitro compounds, specifically aromatic nitro compounds have been widely studied owing to their potential application in e.g. pathology (Ramkishen et al., 2005), materials science (Shinichi & Yuichiro, 2005) and powder technology (Zhang, 2006). These compounds can also be reduced to obtain hydroxylamine, azo-, azoxy compounds and amines, which find applications in dyes, agrochemicals, pharmaceuticals and photographic chemicals (Agrawal & Tratnyek, 1996). In this paper, we report the synthesis and crystal structure of the title compound.
All bond lengths and angles in the title molecule (Fig. 1) are in the expected range (Unver et al., 2002) and in good agreement with those reported previously (Yang et al., 2005). Atoms N1/N2/O1/C1—C6/C14 lie in a plane with the largest deviation being 0.029 Å for atom N2, and atoms N3/N4/O10/C7—C12 also lie in a plane, with the largest deviation being 0.0354 Å for atom N4. The dihedral angle between the two benzene rings is 90.1°, which is considerably larger than found in other biphenyls (Fischer et al., 2007), possibly due to the concomitant effects of steric hindrance of the methoxy and nitro groups. The dihedral angles formed between the benzene ring of C1—C6 and planes N1/O2/O3 and N2/O4/O5 are 24.3 and 70.4°, the dihedral angles formed between the benzene ring of C7—C12 and planes N3/O6/O7 and N4/O8/O9 are 15.7 and 43.0°, respectively. The H atom of the methoxy group forms weak C—H···O intermolecular hydrogen bonds with the nitro group O atom of the neighbouring molecule. The H13B···O5i distance is 2.41 Å, which is considerable shorter than the sum of the van der Waals radii for O and H (2.70 Å). In the crystal structure, molecules are connected to form a one-dimension chain via weak C—H···O hydrogen bonds. In addition, there are also weak C—H···O hydrogen bonds between two one-dimension chains (Fig.2). The H14A···O6ii distance is 2.60 Å. These weak intermolecular C—H···O hydrogen bonds play an important role in stabilizing the crystal structure (symmetry operation: (i) 1 + x,y,z; (ii) 1 - x,1 - y,1 - z).