Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680704891X/cv2310sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680704891X/cv2310Isup2.hkl |
CCDC reference: 667335
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.003 Å
- R factor = 0.044
- wR factor = 0.122
- Data-to-parameter ratio = 13.0
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N1 PLAT320_ALERT_2_C Check Hybridisation of C7 in Main Residue . ?
Alert level G PLAT793_ALERT_1_G Check the Absolute Configuration of C7 = ... R PLAT793_ALERT_1_G Check the Absolute Configuration of C8 = ... S PLAT793_ALERT_1_G Check the Absolute Configuration of C17 = ... R
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related crystal structures, see: Satis Kumar et al. (2006); Chakkaravarthi et al. (2007). Normal ranges of bond lengths and angles in organic compounds have been reported by Allen et al. (1987).
A mixture of 1-(diphenylmethylene)-3-oxo-1,2-aziditinumylide (0.23 g, 1 mmol) and 2-(m-nitro) benzylidine-1,3-indane dione (0.27 g, 1 mmol) was refluxed in dry toluene. The reaction was monitered by TLC. After its completion, the solvent was removed at reduced pressure. The crude product was subjected to column chromatography (silica gel 100–200 mesh) using hexane:ethyl acetate (7:3) as eluant. The compound was recrystallized from hexane:chloroform (1:1) solution.
All H atoms were positioned geometrically (C—H 0.93–0.98 Å, N—H 0.86 Å) and refined using riding model, with Uiso(H) = 1.2Ueq(C,N).
In the title compound, (I) (Fig. 1), all bond lengths and angles are normal (Allen et al., 1987) and correspond to those observed in similar structures (Chakkaravarthi et al., 2007; Satis Kumar et al., 2006).
The benzene ring C1—C6 forms the dihedral angle of 53.26 (6)° with the indan ring system. The phenyl rings C20—C25 and C26—C31 form the dihedral angles of 66.50 (6)° and 58.39 (7)°, respectively, with the indan ring system. The five- (C8/C9/C10/C15/C16) and six-membered (C10—C15) rings in the indane group make a dihedral angle of 4.04 (9)°. The nitro group N1/O3/O4 is twisted out the attached benzene ring at 13.19 (16)°.
The crystal packing of (I) (Fig. 2) is stabilized by intermolecular C—H···O and N—H···O hydrogen bonds (Table 1).
For related crystal structures, see: Satis Kumar et al. (2006); Chakkaravarthi et al. (2007). Normal ranges of bond lengths and angles in organic compounds have been reported by Allen et al. (1987).
Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 (Bruker, 2004); data reduction: APEX2 (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
C31H21N3O5 | Z = 2 |
Mr = 515.51 | F(000) = 536 |
Triclinic, P1 | Dx = 1.347 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.4617 (4) Å | Cell parameters from 7426 reflections |
b = 12.8806 (5) Å | θ = 2.4–25.0° |
c = 12.9114 (8) Å | µ = 0.09 mm−1 |
α = 108.212 (2)° | T = 295 K |
β = 108.535 (3)° | Prism, colourless |
γ = 107.424 (2)° | 0.22 × 0.16 × 0.16 mm |
V = 1270.69 (11) Å3 |
Bruker Kappa-APEXII diffractometer | 4593 independent reflections |
Radiation source: fine-focus sealed tube | 3628 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
ω and φ scans | θmax = 25.3°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −11→11 |
Tmin = 0.897, Tmax = 0.985 | k = −15→15 |
23251 measured reflections | l = −13→15 |
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.122 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0544P)2 + 0.4755P] where P = (Fo2 + 2Fc2)/3 |
4593 reflections | (Δ/σ)max < 0.001 |
352 parameters | Δρmax = 0.41 e Å−3 |
0 restraints | Δρmin = −0.34 e Å−3 |
C31H21N3O5 | γ = 107.424 (2)° |
Mr = 515.51 | V = 1270.69 (11) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.4617 (4) Å | Mo Kα radiation |
b = 12.8806 (5) Å | µ = 0.09 mm−1 |
c = 12.9114 (8) Å | T = 295 K |
α = 108.212 (2)° | 0.22 × 0.16 × 0.16 mm |
β = 108.535 (3)° |
Bruker Kappa-APEXII diffractometer | 4593 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3628 reflections with I > 2σ(I) |
Tmin = 0.897, Tmax = 0.985 | Rint = 0.029 |
23251 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.122 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.41 e Å−3 |
4593 reflections | Δρmin = −0.34 e Å−3 |
352 parameters |
x | y | z | Uiso*/Ueq | ||
O1 | −0.04259 (18) | 0.28990 (11) | 0.30518 (12) | 0.0562 (4) | |
O2 | −0.38449 (18) | −0.09220 (12) | −0.04041 (12) | 0.0600 (4) | |
O3 | −0.4375 (4) | 0.4332 (2) | 0.2466 (3) | 0.1238 (9) | |
O4 | −0.3681 (3) | 0.59338 (18) | 0.2206 (3) | 0.1264 (9) | |
O5 | 0.13052 (18) | 0.34678 (13) | 0.11804 (15) | 0.0704 (5) | |
N1 | −0.3744 (3) | 0.49416 (19) | 0.2027 (2) | 0.0828 (6) | |
N2 | 0.20415 (18) | 0.23100 (13) | 0.19914 (14) | 0.0457 (4) | |
H2A | 0.3038 | 0.2883 | 0.2454 | 0.055* | |
N3 | 0.16360 (17) | 0.12174 (13) | 0.20421 (13) | 0.0406 (3) | |
C1 | −0.1963 (3) | 0.34378 (19) | −0.0334 (2) | 0.0558 (5) | |
H1 | −0.1547 | 0.3114 | −0.0851 | 0.067* | |
C2 | −0.2192 (3) | 0.4456 (2) | −0.0283 (2) | 0.0688 (6) | |
H2 | −0.1950 | 0.4805 | −0.0774 | 0.083* | |
C3 | −0.2776 (3) | 0.49552 (19) | 0.0488 (2) | 0.0651 (6) | |
H3 | −0.2938 | 0.5642 | 0.0529 | 0.078* | |
C4 | −0.3116 (2) | 0.44166 (17) | 0.1199 (2) | 0.0554 (5) | |
C5 | −0.2928 (2) | 0.33816 (16) | 0.11500 (18) | 0.0474 (5) | |
H5 | −0.3192 | 0.3028 | 0.1632 | 0.057* | |
C6 | −0.2340 (2) | 0.28869 (15) | 0.03732 (16) | 0.0408 (4) | |
C7 | −0.2306 (2) | 0.16839 (15) | 0.01203 (15) | 0.0384 (4) | |
H7 | −0.3194 | 0.1049 | −0.0687 | 0.046* | |
C8 | −0.1958 (2) | 0.11749 (14) | 0.10371 (15) | 0.0366 (4) | |
C9 | −0.3020 (2) | −0.01311 (15) | 0.06427 (16) | 0.0399 (4) | |
C10 | −0.2864 (2) | −0.02621 (15) | 0.17684 (16) | 0.0383 (4) | |
C11 | −0.3501 (2) | −0.13041 (17) | 0.18977 (19) | 0.0473 (5) | |
H11 | −0.4181 | −0.2061 | 0.1219 | 0.057* | |
C12 | −0.3093 (3) | −0.1183 (2) | 0.3065 (2) | 0.0568 (5) | |
H12 | −0.3509 | −0.1870 | 0.3176 | 0.068* | |
C13 | −0.2078 (3) | −0.0061 (2) | 0.4074 (2) | 0.0605 (6) | |
H13 | −0.1817 | −0.0006 | 0.4853 | 0.073* | |
C14 | −0.1441 (3) | 0.09819 (19) | 0.39477 (18) | 0.0547 (5) | |
H14 | −0.0760 | 0.1738 | 0.4629 | 0.066* | |
C15 | −0.1851 (2) | 0.08654 (16) | 0.27771 (16) | 0.0408 (4) | |
C16 | −0.1291 (2) | 0.18194 (16) | 0.23871 (16) | 0.0402 (4) | |
C17 | −0.0803 (2) | 0.14712 (15) | 0.04513 (15) | 0.0370 (4) | |
H17 | −0.0884 | 0.0759 | −0.0178 | 0.044* | |
C18 | 0.0907 (2) | 0.25044 (16) | 0.12286 (17) | 0.0428 (4) | |
C19 | 0.2746 (2) | 0.11628 (15) | 0.28863 (15) | 0.0376 (4) | |
C20 | 0.2312 (2) | −0.00189 (15) | 0.29322 (15) | 0.0379 (4) | |
C21 | 0.0669 (2) | −0.08342 (17) | 0.24699 (18) | 0.0490 (5) | |
H21 | −0.0173 | −0.0647 | 0.2100 | 0.059* | |
C22 | 0.0260 (3) | −0.19161 (18) | 0.2548 (2) | 0.0573 (5) | |
H22 | −0.0850 | −0.2443 | 0.2249 | 0.069* | |
C23 | 0.1482 (3) | −0.22227 (18) | 0.30635 (19) | 0.0577 (5) | |
H23 | 0.1204 | −0.2958 | 0.3108 | 0.069* | |
C24 | 0.3110 (3) | −0.14361 (19) | 0.35109 (19) | 0.0591 (5) | |
H24 | 0.3942 | −0.1644 | 0.3853 | 0.071* | |
C25 | 0.3536 (2) | −0.03331 (18) | 0.34610 (18) | 0.0501 (5) | |
H25 | 0.4650 | 0.0201 | 0.3784 | 0.060* | |
C26 | 0.4357 (2) | 0.22278 (15) | 0.38371 (16) | 0.0399 (4) | |
C27 | 0.4430 (3) | 0.29707 (19) | 0.49105 (19) | 0.0573 (5) | |
H27 | 0.3483 | 0.2794 | 0.5029 | 0.069* | |
C28 | 0.5895 (3) | 0.3971 (2) | 0.5805 (2) | 0.0691 (6) | |
H28 | 0.5936 | 0.4462 | 0.6527 | 0.083* | |
C29 | 0.7288 (3) | 0.42418 (19) | 0.5633 (2) | 0.0664 (6) | |
H29 | 0.8272 | 0.4924 | 0.6232 | 0.080* | |
C30 | 0.7234 (3) | 0.3510 (2) | 0.4581 (2) | 0.0684 (6) | |
H30 | 0.8186 | 0.3689 | 0.4470 | 0.082* | |
C31 | 0.5770 (2) | 0.25060 (19) | 0.36821 (19) | 0.0559 (5) | |
H31 | 0.5741 | 0.2014 | 0.2966 | 0.067* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0672 (9) | 0.0370 (7) | 0.0434 (8) | 0.0101 (7) | 0.0201 (7) | 0.0111 (6) |
O2 | 0.0658 (9) | 0.0413 (8) | 0.0422 (8) | 0.0044 (7) | 0.0148 (7) | 0.0117 (7) |
O3 | 0.172 (2) | 0.1117 (17) | 0.180 (2) | 0.0977 (17) | 0.134 (2) | 0.0836 (18) |
O4 | 0.165 (2) | 0.0690 (12) | 0.190 (2) | 0.0774 (14) | 0.111 (2) | 0.0548 (14) |
O5 | 0.0535 (9) | 0.0567 (9) | 0.0936 (12) | 0.0135 (7) | 0.0150 (8) | 0.0547 (9) |
N1 | 0.0938 (16) | 0.0619 (13) | 0.1136 (19) | 0.0499 (12) | 0.0576 (15) | 0.0383 (13) |
N2 | 0.0356 (8) | 0.0403 (8) | 0.0557 (10) | 0.0118 (7) | 0.0133 (7) | 0.0277 (8) |
N3 | 0.0398 (8) | 0.0393 (8) | 0.0456 (9) | 0.0180 (7) | 0.0179 (7) | 0.0234 (7) |
C1 | 0.0592 (13) | 0.0612 (12) | 0.0597 (13) | 0.0285 (10) | 0.0282 (11) | 0.0392 (11) |
C2 | 0.0696 (15) | 0.0650 (14) | 0.0885 (17) | 0.0294 (12) | 0.0341 (14) | 0.0559 (14) |
C3 | 0.0604 (13) | 0.0428 (11) | 0.0872 (17) | 0.0232 (10) | 0.0213 (12) | 0.0357 (12) |
C4 | 0.0493 (11) | 0.0402 (10) | 0.0689 (14) | 0.0207 (9) | 0.0211 (10) | 0.0205 (10) |
C5 | 0.0454 (11) | 0.0407 (10) | 0.0558 (12) | 0.0184 (8) | 0.0211 (9) | 0.0243 (9) |
C6 | 0.0355 (9) | 0.0388 (9) | 0.0429 (10) | 0.0144 (8) | 0.0117 (8) | 0.0206 (8) |
C7 | 0.0398 (9) | 0.0374 (9) | 0.0332 (9) | 0.0152 (7) | 0.0123 (8) | 0.0167 (8) |
C8 | 0.0371 (9) | 0.0335 (9) | 0.0350 (9) | 0.0123 (7) | 0.0146 (8) | 0.0154 (7) |
C9 | 0.0361 (9) | 0.0362 (9) | 0.0420 (10) | 0.0134 (8) | 0.0159 (8) | 0.0157 (8) |
C10 | 0.0345 (9) | 0.0413 (9) | 0.0455 (10) | 0.0182 (8) | 0.0208 (8) | 0.0229 (8) |
C11 | 0.0416 (10) | 0.0445 (10) | 0.0616 (12) | 0.0189 (8) | 0.0252 (9) | 0.0290 (9) |
C12 | 0.0654 (13) | 0.0616 (13) | 0.0750 (15) | 0.0351 (11) | 0.0448 (12) | 0.0474 (12) |
C13 | 0.0814 (16) | 0.0750 (15) | 0.0582 (13) | 0.0449 (13) | 0.0452 (12) | 0.0446 (13) |
C14 | 0.0707 (14) | 0.0575 (12) | 0.0437 (11) | 0.0312 (11) | 0.0312 (10) | 0.0239 (10) |
C15 | 0.0465 (10) | 0.0430 (10) | 0.0418 (10) | 0.0227 (8) | 0.0252 (9) | 0.0215 (8) |
C16 | 0.0419 (10) | 0.0375 (10) | 0.0392 (10) | 0.0162 (8) | 0.0185 (8) | 0.0161 (8) |
C17 | 0.0431 (10) | 0.0364 (9) | 0.0354 (9) | 0.0178 (8) | 0.0191 (8) | 0.0190 (8) |
C18 | 0.0414 (10) | 0.0437 (10) | 0.0479 (11) | 0.0180 (8) | 0.0198 (9) | 0.0272 (9) |
C19 | 0.0375 (9) | 0.0412 (9) | 0.0373 (9) | 0.0200 (8) | 0.0173 (8) | 0.0185 (8) |
C20 | 0.0416 (10) | 0.0401 (9) | 0.0332 (9) | 0.0201 (8) | 0.0162 (8) | 0.0166 (8) |
C21 | 0.0426 (10) | 0.0478 (11) | 0.0590 (12) | 0.0222 (9) | 0.0204 (9) | 0.0273 (10) |
C22 | 0.0537 (12) | 0.0433 (11) | 0.0708 (14) | 0.0163 (9) | 0.0279 (11) | 0.0263 (10) |
C23 | 0.0791 (15) | 0.0439 (11) | 0.0579 (13) | 0.0296 (11) | 0.0321 (12) | 0.0285 (10) |
C24 | 0.0673 (14) | 0.0555 (12) | 0.0573 (13) | 0.0368 (11) | 0.0178 (11) | 0.0301 (11) |
C25 | 0.0458 (11) | 0.0504 (11) | 0.0509 (11) | 0.0231 (9) | 0.0145 (9) | 0.0250 (9) |
C26 | 0.0400 (9) | 0.0382 (9) | 0.0412 (10) | 0.0180 (8) | 0.0160 (8) | 0.0193 (8) |
C27 | 0.0552 (12) | 0.0532 (12) | 0.0556 (13) | 0.0228 (10) | 0.0266 (11) | 0.0148 (10) |
C28 | 0.0760 (16) | 0.0503 (12) | 0.0553 (14) | 0.0252 (12) | 0.0218 (12) | 0.0049 (11) |
C29 | 0.0562 (14) | 0.0425 (11) | 0.0641 (15) | 0.0085 (10) | 0.0078 (11) | 0.0148 (11) |
C30 | 0.0456 (12) | 0.0648 (14) | 0.0737 (16) | 0.0091 (11) | 0.0232 (11) | 0.0255 (13) |
C31 | 0.0478 (12) | 0.0581 (12) | 0.0500 (12) | 0.0159 (10) | 0.0236 (10) | 0.0167 (10) |
O1—C16 | 1.211 (2) | C12—H12 | 0.9300 |
O2—C9 | 1.211 (2) | C13—C14 | 1.381 (3) |
O3—N1 | 1.228 (3) | C13—H13 | 0.9300 |
O4—N1 | 1.205 (3) | C14—C15 | 1.381 (3) |
O5—C18 | 1.212 (2) | C14—H14 | 0.9300 |
N1—C4 | 1.465 (3) | C15—C16 | 1.487 (2) |
N2—C18 | 1.352 (2) | C17—C18 | 1.497 (2) |
N2—N3 | 1.3719 (19) | C17—H17 | 0.9800 |
N2—H2A | 0.8600 | C19—C20 | 1.479 (2) |
N3—C19 | 1.288 (2) | C19—C26 | 1.489 (2) |
C1—C2 | 1.377 (3) | C20—C21 | 1.384 (3) |
C1—C6 | 1.387 (3) | C20—C25 | 1.386 (2) |
C1—H1 | 0.9300 | C21—C22 | 1.375 (3) |
C2—C3 | 1.368 (3) | C21—H21 | 0.9300 |
C2—H2 | 0.9300 | C22—C23 | 1.372 (3) |
C3—C4 | 1.371 (3) | C22—H22 | 0.9300 |
C3—H3 | 0.9300 | C23—C24 | 1.367 (3) |
C4—C5 | 1.382 (3) | C23—H23 | 0.9300 |
C5—C6 | 1.374 (3) | C24—C25 | 1.384 (3) |
C5—H5 | 0.9300 | C24—H24 | 0.9300 |
C6—C7 | 1.493 (2) | C25—H25 | 0.9300 |
C7—C17 | 1.483 (2) | C26—C31 | 1.373 (3) |
C7—C8 | 1.519 (2) | C26—C27 | 1.382 (3) |
C7—H7 | 0.9800 | C27—C28 | 1.377 (3) |
C8—C16 | 1.486 (2) | C27—H27 | 0.9300 |
C8—C9 | 1.492 (2) | C28—C29 | 1.367 (3) |
C8—C17 | 1.538 (2) | C28—H28 | 0.9300 |
C9—C10 | 1.481 (2) | C29—C30 | 1.364 (3) |
C10—C11 | 1.383 (2) | C29—H29 | 0.9300 |
C10—C15 | 1.384 (2) | C30—C31 | 1.380 (3) |
C11—C12 | 1.375 (3) | C30—H30 | 0.9300 |
C11—H11 | 0.9300 | C31—H31 | 0.9300 |
C12—C13 | 1.380 (3) | ||
O4—N1—O3 | 122.9 (2) | C14—C15—C10 | 120.78 (17) |
O4—N1—C4 | 118.4 (2) | C14—C15—C16 | 128.81 (17) |
O3—N1—C4 | 118.68 (19) | C10—C15—C16 | 110.37 (15) |
C18—N2—N3 | 121.34 (14) | O1—C16—C8 | 127.48 (16) |
C18—N2—H2A | 119.3 | O1—C16—C15 | 126.23 (16) |
N3—N2—H2A | 119.3 | C8—C16—C15 | 106.26 (14) |
C19—N3—N2 | 116.68 (14) | C7—C17—C18 | 121.70 (15) |
C2—C1—C6 | 121.1 (2) | C7—C17—C8 | 60.32 (11) |
C2—C1—H1 | 119.4 | C18—C17—C8 | 119.45 (14) |
C6—C1—H1 | 119.4 | C7—C17—H17 | 114.9 |
C3—C2—C1 | 120.2 (2) | C18—C17—H17 | 114.9 |
C3—C2—H2 | 119.9 | C8—C17—H17 | 114.9 |
C1—C2—H2 | 119.9 | O5—C18—N2 | 120.11 (17) |
C2—C3—C4 | 118.20 (19) | O5—C18—C17 | 123.29 (16) |
C2—C3—H3 | 120.9 | N2—C18—C17 | 116.58 (15) |
C4—C3—H3 | 120.9 | N3—C19—C20 | 116.59 (15) |
C3—C4—C5 | 122.9 (2) | N3—C19—C26 | 123.70 (15) |
C3—C4—N1 | 118.74 (19) | C20—C19—C26 | 119.60 (14) |
C5—C4—N1 | 118.3 (2) | C21—C20—C25 | 118.00 (16) |
C6—C5—C4 | 118.45 (18) | C21—C20—C19 | 120.89 (15) |
C6—C5—H5 | 120.8 | C25—C20—C19 | 121.10 (16) |
C4—C5—H5 | 120.8 | C22—C21—C20 | 121.12 (18) |
C5—C6—C1 | 119.13 (17) | C22—C21—H21 | 119.4 |
C5—C6—C7 | 122.89 (16) | C20—C21—H21 | 119.4 |
C1—C6—C7 | 117.43 (17) | C23—C22—C21 | 120.37 (19) |
C17—C7—C6 | 126.45 (15) | C23—C22—H22 | 119.8 |
C17—C7—C8 | 61.64 (11) | C21—C22—H22 | 119.8 |
C6—C7—C8 | 125.85 (15) | C24—C23—C22 | 119.34 (18) |
C17—C7—H7 | 111.4 | C24—C23—H23 | 120.3 |
C6—C7—H7 | 111.4 | C22—C23—H23 | 120.3 |
C8—C7—H7 | 111.4 | C23—C24—C25 | 120.73 (19) |
C16—C8—C9 | 106.86 (14) | C23—C24—H24 | 119.6 |
C16—C8—C7 | 128.31 (14) | C25—C24—H24 | 119.6 |
C9—C8—C7 | 118.67 (14) | C24—C25—C20 | 120.42 (19) |
C16—C8—C17 | 119.38 (14) | C24—C25—H25 | 119.8 |
C9—C8—C17 | 118.39 (14) | C20—C25—H25 | 119.8 |
C7—C8—C17 | 58.04 (11) | C31—C26—C27 | 118.73 (18) |
O2—C9—C10 | 127.28 (16) | C31—C26—C19 | 122.37 (17) |
O2—C9—C8 | 125.76 (16) | C27—C26—C19 | 118.90 (16) |
C10—C9—C8 | 106.96 (14) | C28—C27—C26 | 120.5 (2) |
C11—C10—C15 | 121.26 (17) | C28—C27—H27 | 119.7 |
C11—C10—C9 | 129.33 (17) | C26—C27—H27 | 119.7 |
C15—C10—C9 | 109.33 (14) | C29—C28—C27 | 120.1 (2) |
C12—C11—C10 | 117.74 (19) | C29—C28—H28 | 120.0 |
C12—C11—H11 | 121.1 | C27—C28—H28 | 120.0 |
C10—C11—H11 | 121.1 | C30—C29—C28 | 119.9 (2) |
C11—C12—C13 | 121.18 (18) | C30—C29—H29 | 120.0 |
C11—C12—H12 | 119.4 | C28—C29—H29 | 120.0 |
C13—C12—H12 | 119.4 | C29—C30—C31 | 120.2 (2) |
C12—C13—C14 | 121.23 (19) | C29—C30—H30 | 119.9 |
C12—C13—H13 | 119.4 | C31—C30—H30 | 119.9 |
C14—C13—H13 | 119.4 | C26—C31—C30 | 120.5 (2) |
C13—C14—C15 | 117.80 (19) | C26—C31—H31 | 119.7 |
C13—C14—H14 | 121.1 | C30—C31—H31 | 119.7 |
C15—C14—H14 | 121.1 | ||
C18—N2—N3—C19 | −172.85 (17) | C9—C8—C16—C15 | 4.82 (18) |
C6—C1—C2—C3 | 1.1 (3) | C7—C8—C16—C15 | 156.24 (16) |
C1—C2—C3—C4 | 0.1 (3) | C17—C8—C16—C15 | −132.99 (15) |
C2—C3—C4—C5 | −1.4 (3) | C14—C15—C16—O1 | −4.2 (3) |
C2—C3—C4—N1 | −179.9 (2) | C10—C15—C16—O1 | 178.21 (18) |
O4—N1—C4—C3 | −12.1 (4) | C14—C15—C16—C8 | 173.92 (19) |
O3—N1—C4—C3 | 164.8 (3) | C10—C15—C16—C8 | −3.63 (19) |
O4—N1—C4—C5 | 169.4 (2) | C6—C7—C17—C18 | 7.1 (3) |
O3—N1—C4—C5 | −13.8 (4) | C8—C7—C17—C18 | −108.25 (17) |
C3—C4—C5—C6 | 1.4 (3) | C6—C7—C17—C8 | 115.38 (19) |
N1—C4—C5—C6 | 179.94 (18) | C16—C8—C17—C7 | −119.16 (17) |
C4—C5—C6—C1 | −0.2 (3) | C9—C8—C17—C7 | 107.79 (17) |
C4—C5—C6—C7 | −171.44 (17) | C16—C8—C17—C18 | −7.3 (2) |
C2—C1—C6—C5 | −1.1 (3) | C9—C8—C17—C18 | −140.32 (16) |
C2—C1—C6—C7 | 170.69 (19) | C7—C8—C17—C18 | 111.88 (17) |
C5—C6—C7—C17 | −114.6 (2) | N3—N2—C18—O5 | −178.34 (18) |
C1—C6—C7—C17 | 74.0 (2) | N3—N2—C18—C17 | 0.2 (3) |
C5—C6—C7—C8 | −35.8 (3) | C7—C17—C18—O5 | −35.5 (3) |
C1—C6—C7—C8 | 152.77 (17) | C8—C17—C18—O5 | −106.8 (2) |
C17—C7—C8—C16 | 104.13 (19) | C7—C17—C18—N2 | 146.06 (17) |
C6—C7—C8—C16 | −12.2 (3) | C8—C17—C18—N2 | 74.7 (2) |
C17—C7—C8—C9 | −107.32 (17) | N2—N3—C19—C20 | −179.47 (14) |
C6—C7—C8—C9 | 136.39 (17) | N2—N3—C19—C26 | 4.4 (2) |
C6—C7—C8—C17 | −116.29 (19) | N3—C19—C20—C21 | −25.2 (2) |
C16—C8—C9—O2 | 175.67 (18) | C26—C19—C20—C21 | 151.17 (17) |
C7—C8—C9—O2 | 21.0 (3) | N3—C19—C20—C25 | 156.18 (17) |
C17—C8—C9—O2 | −46.0 (2) | C26—C19—C20—C25 | −27.5 (2) |
C16—C8—C9—C10 | −4.34 (18) | C25—C20—C21—C22 | 0.9 (3) |
C7—C8—C9—C10 | −159.01 (15) | C19—C20—C21—C22 | −177.76 (18) |
C17—C8—C9—C10 | 133.95 (15) | C20—C21—C22—C23 | −1.5 (3) |
O2—C9—C10—C11 | 5.5 (3) | C21—C22—C23—C24 | 0.7 (3) |
C8—C9—C10—C11 | −174.53 (17) | C22—C23—C24—C25 | 0.7 (3) |
O2—C9—C10—C15 | −177.83 (18) | C23—C24—C25—C20 | −1.3 (3) |
C8—C9—C10—C15 | 2.17 (19) | C21—C20—C25—C24 | 0.5 (3) |
C15—C10—C11—C12 | 0.0 (3) | C19—C20—C25—C24 | 179.18 (18) |
C9—C10—C11—C12 | 176.39 (17) | N3—C19—C26—C31 | −91.3 (2) |
C10—C11—C12—C13 | −0.3 (3) | C20—C19—C26—C31 | 92.6 (2) |
C11—C12—C13—C14 | 0.4 (3) | N3—C19—C26—C27 | 88.1 (2) |
C12—C13—C14—C15 | −0.2 (3) | C20—C19—C26—C27 | −88.0 (2) |
C13—C14—C15—C10 | −0.1 (3) | C31—C26—C27—C28 | 0.1 (3) |
C13—C14—C15—C16 | −177.40 (18) | C19—C26—C27—C28 | −179.36 (19) |
C11—C10—C15—C14 | 0.2 (3) | C26—C27—C28—C29 | 0.5 (3) |
C9—C10—C15—C14 | −176.87 (17) | C27—C28—C29—C30 | −1.0 (4) |
C11—C10—C15—C16 | 177.93 (16) | C28—C29—C30—C31 | 0.9 (4) |
C9—C10—C15—C16 | 0.9 (2) | C27—C26—C31—C30 | −0.2 (3) |
C9—C8—C16—O1 | −177.06 (18) | C19—C26—C31—C30 | 179.25 (19) |
C7—C8—C16—O1 | −25.6 (3) | C29—C30—C31—C26 | −0.3 (4) |
C17—C8—C16—O1 | 45.1 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O5i | 0.93 | 2.39 | 3.227 (2) | 149 |
C29—H29···O1ii | 0.93 | 2.57 | 3.406 (2) | 149 |
N2—H2A···O3iii | 0.86 | 2.59 | 3.324 (3) | 144 |
Symmetry codes: (i) −x, −y+1, −z; (ii) −x+1, −y+1, −z+1; (iii) x+1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C31H21N3O5 |
Mr | 515.51 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 295 |
a, b, c (Å) | 9.4617 (4), 12.8806 (5), 12.9114 (8) |
α, β, γ (°) | 108.212 (2), 108.535 (3), 107.424 (2) |
V (Å3) | 1270.69 (11) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.22 × 0.16 × 0.16 |
Data collection | |
Diffractometer | Bruker Kappa-APEXII |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.897, 0.985 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 23251, 4593, 3628 |
Rint | 0.029 |
(sin θ/λ)max (Å−1) | 0.601 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.122, 1.02 |
No. of reflections | 4593 |
No. of parameters | 352 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.41, −0.34 |
Computer programs: APEX2 (Bruker, 2004), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O5i | 0.93 | 2.39 | 3.227 (2) | 149 |
C29—H29···O1ii | 0.93 | 2.57 | 3.406 (2) | 149 |
N2—H2A···O3iii | 0.86 | 2.59 | 3.324 (3) | 144 |
Symmetry codes: (i) −x, −y+1, −z; (ii) −x+1, −y+1, −z+1; (iii) x+1, y, z. |
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In the title compound, (I) (Fig. 1), all bond lengths and angles are normal (Allen et al., 1987) and correspond to those observed in similar structures (Chakkaravarthi et al., 2007; Satis Kumar et al., 2006).
The benzene ring C1—C6 forms the dihedral angle of 53.26 (6)° with the indan ring system. The phenyl rings C20—C25 and C26—C31 form the dihedral angles of 66.50 (6)° and 58.39 (7)°, respectively, with the indan ring system. The five- (C8/C9/C10/C15/C16) and six-membered (C10—C15) rings in the indane group make a dihedral angle of 4.04 (9)°. The nitro group N1/O3/O4 is twisted out the attached benzene ring at 13.19 (16)°.
The crystal packing of (I) (Fig. 2) is stabilized by intermolecular C—H···O and N—H···O hydrogen bonds (Table 1).