| Literature DB >> 23476624 |
Kokichi Nanaura1, Tsunehisa Okuno.
Abstract
In the title compound, C14H11N3O5, the dihedral angles between the amide group (r.m.s. deviation = 0.0429 Å) and the two benzene rings are 39.66 (6) and 63.04 (7)°. The dihedral angle between the benzene rings is 86.04 (7)°. The benzene rings form dihedral angles of 4.42 (5) and 8.91 (5)° with the adjacent nitro groups. In the crystal, mol-ecules are linked via a pair of C-H⋯O hydrogen bonds, forming inversion dimers, which are linked via a second pair of C-H⋯O hydrogen bonds, forming chains propagating along [100].Entities:
Year: 2013 PMID: 23476624 PMCID: PMC3588481 DOI: 10.1107/S1600536813005175
Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN: 1600-5368
| C14H11N3O5 | |
| Triclinic, | |
| Hall symbol: -P 1 | Mo |
| Cell parameters from 1648 reflections | |
| θ = 1.8–25.0° | |
| µ = 0.11 mm−1 | |
| α = 81.449 (10)° | |
| β = 74.676 (10)° | Platelet, colourless |
| γ = 88.062 (13)° | 0.10 × 0.10 × 0.08 mm |
| Rigaku Saturn724+ diffractometer | 2038 reflections with |
| Detector resolution: 28.445 pixels mm-1 | |
| ω scans | θmax = 25.0° |
| Absorption correction: numerical ( | |
| 4684 measured reflections | |
| 2397 independent reflections |
| Refinement on | Secondary atom site location: difference Fourier map |
| Hydrogen site location: inferred from neighbouring sites | |
| H-atom parameters constrained | |
| 2397 reflections | (Δ/σ)max < 0.001 |
| 200 parameters | Δρmax = 0.27 e Å−3 |
| 0 restraints | Δρmin = −0.27 e Å−3 |
| Primary atom site location: structure-invariant direct methods |
| Refinement. Refinement was performed using all reflections. The weighted |
| O1 | −0.5557 (2) | −0.5404 (2) | 0.37979 (13) | 0.0390 (4) | |
| O2 | −0.3035 (2) | −0.6254 (2) | 0.26745 (17) | 0.0472 (5) | |
| O3 | 0.74805 (19) | 0.2913 (3) | −0.02433 (13) | 0.0439 (5) | |
| O4 | 0.5763 (3) | 0.3680 (3) | −0.13945 (14) | 0.0527 (6) | |
| O5 | −0.19693 (17) | 0.09710 (17) | 0.50403 (11) | 0.0252 (4) | |
| N1 | −0.03594 (19) | 0.0866 (2) | 0.31681 (13) | 0.0197 (4) | |
| N2 | −0.3953 (3) | −0.5182 (3) | 0.31981 (16) | 0.0303 (5) | |
| N3 | 0.5958 (3) | 0.3042 (3) | −0.04519 (14) | 0.0297 (5) | |
| C1 | −0.1318 (3) | −0.0612 (3) | 0.31114 (15) | 0.0202 (4) | |
| C2 | −0.3232 (3) | −0.0792 (3) | 0.35967 (16) | 0.0220 (5) | |
| C3 | −0.4102 (3) | −0.2286 (3) | 0.36144 (16) | 0.0234 (5) | |
| C4 | −0.3058 (3) | −0.3557 (3) | 0.31174 (16) | 0.0235 (5) | |
| C5 | −0.1181 (3) | −0.3371 (3) | 0.25680 (17) | 0.0252 (5) | |
| C6 | −0.0311 (3) | −0.1892 (3) | 0.25763 (17) | 0.0247 (5) | |
| C7 | 0.1247 (3) | 0.1395 (3) | 0.22310 (16) | 0.0214 (5) | |
| C8 | 0.3012 (3) | 0.1129 (3) | 0.24046 (17) | 0.0300 (5) | |
| C9 | 0.4555 (3) | 0.1664 (3) | 0.15180 (17) | 0.0307 (5) | |
| C10 | 0.4306 (3) | 0.2425 (3) | 0.04780 (16) | 0.0238 (5) | |
| C11 | 0.2570 (3) | 0.2667 (3) | 0.02760 (17) | 0.0330 (5) | |
| C12 | 0.1024 (3) | 0.2137 (3) | 0.11739 (17) | 0.0299 (5) | |
| C13 | −0.0767 (3) | 0.1569 (3) | 0.41913 (16) | 0.0213 (5) | |
| C14 | 0.0321 (3) | 0.3092 (3) | 0.42132 (18) | 0.0290 (5) | |
| H2 | −0.3936 | 0.0110 | 0.3914 | 0.0264* | |
| H3 | −0.5398 | −0.2433 | 0.3963 | 0.0280* | |
| H5 | −0.0506 | −0.4242 | 0.2193 | 0.0302* | |
| H6 | 0.0982 | −0.1747 | 0.2215 | 0.0297* | |
| H8 | 0.3154 | 0.0582 | 0.3129 | 0.0360* | |
| H9 | 0.5769 | 0.1508 | 0.1627 | 0.0368* | |
| H11 | 0.2438 | 0.3183 | −0.0458 | 0.0396* | |
| H12 | −0.0188 | 0.2285 | 0.1060 | 0.0358* | |
| H14A | 0.0786 | 0.3679 | 0.3422 | 0.0347* | |
| H14B | 0.1373 | 0.2749 | 0.4538 | 0.0347* | |
| H14C | −0.0486 | 0.3841 | 0.4695 | 0.0347* |
| O1 | 0.0354 (9) | 0.0405 (10) | 0.0406 (9) | −0.0158 (7) | −0.0123 (7) | 0.0037 (8) |
| O2 | 0.0371 (9) | 0.0279 (9) | 0.0846 (14) | 0.0051 (7) | −0.0246 (9) | −0.0190 (9) |
| O3 | 0.0219 (8) | 0.0775 (14) | 0.0301 (9) | −0.0079 (8) | −0.0056 (7) | −0.0009 (9) |
| O4 | 0.0369 (9) | 0.0839 (15) | 0.0282 (9) | −0.0039 (9) | −0.0072 (7) | 0.0190 (9) |
| O5 | 0.0200 (7) | 0.0326 (8) | 0.0224 (7) | 0.0023 (6) | −0.0038 (6) | −0.0061 (6) |
| N1 | 0.0151 (8) | 0.0236 (9) | 0.0205 (8) | −0.0001 (6) | −0.0051 (6) | −0.0026 (7) |
| N2 | 0.0272 (10) | 0.0289 (10) | 0.0390 (10) | −0.0025 (8) | −0.0184 (8) | −0.0001 (8) |
| N3 | 0.0267 (9) | 0.0390 (11) | 0.0221 (9) | −0.0034 (8) | −0.0047 (7) | −0.0027 (8) |
| C1 | 0.0174 (9) | 0.0244 (10) | 0.0198 (9) | 0.0003 (8) | −0.0080 (7) | −0.0006 (8) |
| C2 | 0.0171 (9) | 0.0281 (11) | 0.0215 (9) | 0.0042 (8) | −0.0066 (8) | −0.0037 (8) |
| C3 | 0.0158 (9) | 0.0306 (11) | 0.0237 (10) | −0.0009 (8) | −0.0067 (8) | −0.0008 (9) |
| C4 | 0.0221 (10) | 0.0233 (11) | 0.0266 (10) | −0.0025 (8) | −0.0118 (8) | 0.0017 (8) |
| C5 | 0.0213 (10) | 0.0262 (11) | 0.0299 (11) | 0.0040 (8) | −0.0087 (8) | −0.0073 (9) |
| C6 | 0.0154 (9) | 0.0303 (11) | 0.0283 (10) | 0.0016 (8) | −0.0051 (8) | −0.0052 (9) |
| C7 | 0.0186 (9) | 0.0236 (10) | 0.0227 (10) | −0.0017 (8) | −0.0056 (8) | −0.0050 (8) |
| C8 | 0.0226 (10) | 0.0429 (13) | 0.0232 (10) | −0.0003 (9) | −0.0080 (8) | 0.0034 (9) |
| C9 | 0.0179 (10) | 0.0480 (14) | 0.0268 (11) | −0.0016 (9) | −0.0083 (8) | −0.0025 (10) |
| C10 | 0.0198 (10) | 0.0280 (11) | 0.0228 (10) | −0.0026 (8) | −0.0034 (8) | −0.0048 (9) |
| C11 | 0.0289 (11) | 0.0468 (14) | 0.0220 (10) | 0.0019 (10) | −0.0092 (9) | 0.0032 (10) |
| C12 | 0.0192 (10) | 0.0457 (13) | 0.0257 (10) | −0.0003 (9) | −0.0093 (8) | −0.0021 (10) |
| C13 | 0.0167 (9) | 0.0247 (11) | 0.0243 (10) | 0.0062 (8) | −0.0089 (8) | −0.0039 (8) |
| C14 | 0.0300 (11) | 0.0314 (12) | 0.0279 (11) | −0.0031 (9) | −0.0104 (9) | −0.0062 (9) |
| O1—N2 | 1.226 (3) | C7—C12 | 1.376 (3) |
| O2—N2 | 1.229 (3) | C8—C9 | 1.379 (3) |
| O3—N3 | 1.224 (3) | C9—C10 | 1.369 (3) |
| O4—N3 | 1.221 (3) | C10—C11 | 1.382 (3) |
| O5—C13 | 1.218 (2) | C11—C12 | 1.386 (3) |
| N1—C1 | 1.430 (3) | C13—C14 | 1.502 (3) |
| N1—C7 | 1.439 (2) | C2—H2 | 0.950 |
| N1—C13 | 1.393 (3) | C3—H3 | 0.950 |
| N2—C4 | 1.470 (3) | C5—H5 | 0.950 |
| N3—C10 | 1.473 (3) | C6—H6 | 0.950 |
| C1—C2 | 1.395 (3) | C8—H8 | 0.950 |
| C1—C6 | 1.392 (3) | C9—H9 | 0.950 |
| C2—C3 | 1.383 (3) | C11—H11 | 0.950 |
| C3—C4 | 1.379 (3) | C12—H12 | 0.950 |
| C4—C5 | 1.384 (3) | C14—H14A | 0.980 |
| C5—C6 | 1.380 (3) | C14—H14B | 0.980 |
| C7—C8 | 1.391 (3) | C14—H14C | 0.980 |
| O1···C3 | 2.730 (3) | H11···H12 | 2.3500 |
| O1···C5 | 3.552 (3) | H12···H14A | 3.4692 |
| O2···C3 | 3.551 (3) | O1···H3i | 3.2240 |
| O2···C5 | 2.716 (3) | O1···H14Aiii | 3.0122 |
| O3···C9 | 2.712 (3) | O1···H14Biii | 2.6480 |
| O3···C11 | 3.554 (3) | O1···H14Ciii | 3.5911 |
| O4···C9 | 3.543 (3) | O1···H14Cix | 3.3464 |
| O4···C11 | 2.740 (3) | O2···H2iv | 3.0985 |
| O5···C1 | 2.746 (3) | O2···H9iii | 2.6542 |
| O5···C2 | 2.765 (3) | O2···H11ii | 3.3131 |
| O5···C7 | 3.576 (3) | O2···H12iv | 2.8331 |
| C1···C4 | 2.744 (3) | O2···H14Aiv | 3.2039 |
| C1···C8 | 3.408 (3) | O2···H14Civ | 3.4762 |
| C1···C12 | 3.163 (3) | O3···H5v | 2.8961 |
| C2···C5 | 2.786 (3) | O3···H6v | 2.6499 |
| C2···C13 | 2.977 (3) | O3···H11vi | 3.3887 |
| C3···C6 | 2.780 (3) | O3···H12vii | 2.6276 |
| C6···C7 | 2.860 (3) | O4···H3ii | 3.4790 |
| C6···C8 | 3.480 (4) | O4···H5v | 3.4369 |
| C6···C12 | 3.481 (4) | O4···H6v | 2.8701 |
| C6···C13 | 3.595 (4) | O4···H14Avi | 3.5560 |
| C7···C10 | 2.725 (3) | O5···H2ix | 3.0802 |
| C7···C14 | 2.850 (4) | O5···H3ix | 2.3895 |
| C8···C11 | 2.780 (3) | O5···H8viii | 2.3362 |
| C8···C13 | 3.109 (3) | O5···H14Bviii | 3.0071 |
| C8···C14 | 3.131 (3) | N2···H3i | 3.5938 |
| C9···C12 | 2.776 (3) | N2···H9iii | 3.5400 |
| C12···C13 | 3.500 (3) | N2···H11ii | 3.3749 |
| O1···O1i | 3.380 (3) | N2···H14Civ | 3.5320 |
| O1···O4ii | 3.067 (3) | N3···H5v | 3.5638 |
| O1···C3i | 3.345 (3) | N3···H6v | 2.9605 |
| O1···C4i | 3.570 (3) | C1···H9xii | 3.4281 |
| O1···C14iii | 3.228 (3) | C1···H14Bviii | 3.0862 |
| O2···O4ii | 3.355 (3) | C2···H2ix | 3.2949 |
| O2···N1iv | 3.105 (3) | C2···H8xii | 3.0367 |
| O2···C9iii | 3.199 (4) | C2···H9xii | 3.0316 |
| O2···C12iv | 3.415 (3) | C2···H14Bviii | 3.1521 |
| O2···C13iv | 3.128 (3) | C3···H8xii | 3.1294 |
| O2···C14iv | 3.474 (4) | C3···H14Bviii | 3.3704 |
| O3···C5v | 3.361 (3) | C4···H11ii | 3.0913 |
| O3···C6v | 3.240 (3) | C4···H14Bviii | 3.5370 |
| O3···C11vi | 3.560 (4) | C4···H14Civ | 3.4905 |
| O3···C12vii | 3.501 (3) | C5···H11ii | 2.9211 |
| O4···O1ii | 3.067 (3) | C5···H14Aiv | 2.9518 |
| O4···O2ii | 3.355 (3) | C5···H14Bviii | 3.5699 |
| O4···N2ii | 2.948 (3) | C5···H14Civ | 3.2916 |
| O4···C3ii | 3.568 (4) | C6···H14Bviii | 3.3341 |
| O4···C4ii | 3.270 (3) | C8···H2vii | 3.2859 |
| O4···C10vi | 3.479 (4) | C8···H3vii | 3.5429 |
| O5···O5viii | 3.266 (3) | C9···H2vii | 3.4298 |
| O5···N1viii | 3.279 (3) | C12···H5x | 3.3853 |
| O5···C2ix | 3.518 (3) | C13···H3ix | 3.2539 |
| O5···C3ix | 3.183 (3) | C13···H8viii | 3.4855 |
| O5···C8viii | 3.204 (3) | C13···H14Bviii | 3.5847 |
| O5···C13viii | 3.062 (3) | C14···H5x | 3.1790 |
| O5···C14viii | 3.536 (3) | C14···H14Cxiii | 2.9936 |
| N1···O2x | 3.105 (3) | H2···O2x | 3.0985 |
| N1···O5viii | 3.279 (3) | H2···O5ix | 3.0802 |
| N2···O4ii | 2.948 (3) | H2···C2ix | 3.2949 |
| C2···O5ix | 3.518 (3) | H2···C8xii | 3.2859 |
| C3···O1i | 3.345 (3) | H2···C9xii | 3.4298 |
| C3···O4ii | 3.568 (4) | H2···H2ix | 2.6662 |
| C3···O5ix | 3.183 (3) | H2···H3ix | 3.3208 |
| C4···O1i | 3.570 (3) | H2···H8xii | 2.5836 |
| C4···O4ii | 3.270 (3) | H2···H9xii | 2.8867 |
| C5···O3v | 3.361 (3) | H2···H14Bviii | 3.5740 |
| C5···C14iv | 3.553 (3) | H3···O1i | 3.2240 |
| C6···O3v | 3.240 (3) | H3···O4ii | 3.4790 |
| C8···O5viii | 3.204 (3) | H3···O5ix | 2.3895 |
| C9···O2xi | 3.199 (4) | H3···N2i | 3.5938 |
| C10···O4vi | 3.479 (4) | H3···C8xii | 3.5429 |
| C11···O3vi | 3.560 (4) | H3···C13ix | 3.2539 |
| C12···O2x | 3.415 (3) | H3···H2ix | 3.3208 |
| C12···O3xii | 3.501 (3) | H3···H8xii | 2.7875 |
| C13···O2x | 3.128 (3) | H3···H14Cix | 3.2232 |
| C13···O5viii | 3.062 (3) | H5···O3v | 2.8961 |
| C13···C13viii | 3.324 (3) | H5···O4v | 3.4369 |
| C14···O1xi | 3.228 (3) | H5···N3v | 3.5638 |
| C14···O2x | 3.474 (4) | H5···C12iv | 3.3853 |
| C14···O5viii | 3.536 (3) | H5···C14iv | 3.1790 |
| C14···C5x | 3.553 (3) | H5···H11ii | 2.8595 |
| O1···H3 | 2.4445 | H5···H12iv | 3.2729 |
| O2···H5 | 2.4240 | H5···H14Aiv | 2.4184 |
| O3···H9 | 2.4141 | H5···H14Civ | 3.1864 |
| O4···H11 | 2.4557 | H6···O3v | 2.6499 |
| O5···H2 | 2.4258 | H6···O4v | 2.8701 |
| O5···H14A | 3.1191 | H6···N3v | 2.9605 |
| O5···H14B | 2.7956 | H8···O5viii | 2.3362 |
| O5···H14C | 2.5300 | H8···C2vii | 3.0367 |
| N1···H2 | 2.6396 | H8···C3vii | 3.1294 |
| N1···H6 | 2.5961 | H8···C13viii | 3.4855 |
| N1···H8 | 2.6096 | H8···H2vii | 2.5836 |
| N1···H12 | 2.6044 | H8···H3vii | 2.7875 |
| N1···H14A | 2.5407 | H9···O2xi | 2.6542 |
| N1···H14B | 2.9533 | H9···N2xi | 3.5400 |
| N1···H14C | 3.2219 | H9···C1vii | 3.4281 |
| N2···H3 | 2.6186 | H9···C2vii | 3.0316 |
| N2···H5 | 2.6197 | H9···H2vii | 2.8867 |
| N3···H9 | 2.5992 | H9···H12vii | 2.9759 |
| N3···H11 | 2.6241 | H11···O2ii | 3.3131 |
| C1···H3 | 3.2660 | H11···O3vi | 3.3887 |
| C1···H5 | 3.2663 | H11···N2ii | 3.3749 |
| C1···H8 | 3.5073 | H11···C4ii | 3.0913 |
| C1···H12 | 3.1019 | H11···C5ii | 2.9211 |
| C2···H6 | 3.2698 | H11···H5ii | 2.8595 |
| C3···H5 | 3.2729 | H12···O2x | 2.8331 |
| C4···H2 | 3.2393 | H12···O3xii | 2.6276 |
| C4···H6 | 3.2372 | H12···H5x | 3.2729 |
| C5···H3 | 3.2729 | H12···H9xii | 2.9759 |
| C6···H2 | 3.2704 | H14A···O1xi | 3.0122 |
| C6···H8 | 3.5719 | H14A···O2x | 3.2039 |
| C6···H12 | 3.5807 | H14A···O4vi | 3.5560 |
| C7···H6 | 2.5530 | H14A···C5x | 2.9518 |
| C7···H9 | 3.2561 | H14A···H5x | 2.4184 |
| C7···H11 | 3.2541 | H14A···H14Cxiii | 3.2074 |
| C7···H14A | 2.4635 | H14B···O1xi | 2.6480 |
| C7···H14B | 3.1646 | H14B···O5viii | 3.0071 |
| C8···H6 | 2.8821 | H14B···C1viii | 3.0862 |
| C8···H12 | 3.2625 | H14B···C2viii | 3.1521 |
| C8···H14A | 2.8181 | H14B···C3viii | 3.3704 |
| C8···H14B | 3.0116 | H14B···C4viii | 3.5370 |
| C9···H11 | 3.2675 | H14B···C5viii | 3.5699 |
| C10···H8 | 3.2278 | H14B···C6viii | 3.3341 |
| C10···H12 | 3.2382 | H14B···C13viii | 3.5847 |
| C11···H9 | 3.2672 | H14B···H2viii | 3.5740 |
| C12···H6 | 3.1965 | H14B···H14Cxiii | 3.0306 |
| C12···H8 | 3.2615 | H14C···O1xi | 3.5911 |
| C12···H14A | 3.1125 | H14C···O1ix | 3.3464 |
| C13···H2 | 2.7932 | H14C···O2x | 3.4762 |
| C13···H8 | 2.9975 | H14C···N2x | 3.5320 |
| C14···H8 | 3.0518 | H14C···C4x | 3.4905 |
| H2···H3 | 2.3419 | H14C···C5x | 3.2916 |
| H5···H6 | 2.3380 | H14C···C14xiii | 2.9936 |
| H6···H8 | 3.0232 | H14C···H3ix | 3.2232 |
| H6···H12 | 3.5205 | H14C···H5x | 3.1864 |
| H8···H9 | 2.3401 | H14C···H14Axiii | 3.2074 |
| H8···H14A | 3.0202 | H14C···H14Bxiii | 3.0306 |
| H8···H14B | 2.6923 | H14C···H14Cxiii | 2.3144 |
| C1—N1—C7 | 117.73 (16) | C10—C11—C12 | 118.19 (19) |
| C1—N1—C13 | 120.10 (14) | C7—C12—C11 | 119.90 (19) |
| C7—N1—C13 | 121.12 (17) | O5—C13—N1 | 121.08 (18) |
| O1—N2—O2 | 123.71 (19) | O5—C13—C14 | 121.06 (19) |
| O1—N2—C4 | 118.39 (17) | N1—C13—C14 | 117.86 (15) |
| O2—N2—C4 | 117.88 (16) | C1—C2—H2 | 120.083 |
| O3—N3—O4 | 122.36 (16) | C3—C2—H2 | 120.077 |
| O3—N3—C10 | 118.43 (17) | C2—C3—H3 | 120.539 |
| O4—N3—C10 | 119.20 (17) | C4—C3—H3 | 120.544 |
| N1—C1—C2 | 120.95 (17) | C4—C5—H5 | 120.727 |
| N1—C1—C6 | 119.08 (15) | C6—C5—H5 | 120.731 |
| C2—C1—C6 | 119.96 (19) | C1—C6—H6 | 119.844 |
| C1—C2—C3 | 119.84 (18) | C5—C6—H6 | 119.836 |
| C2—C3—C4 | 118.92 (16) | C7—C8—H8 | 120.234 |
| N2—C4—C3 | 119.07 (16) | C9—C8—H8 | 120.228 |
| N2—C4—C5 | 118.67 (17) | C8—C9—H9 | 120.571 |
| C3—C4—C5 | 122.24 (19) | C10—C9—H9 | 120.567 |
| C4—C5—C6 | 118.54 (18) | C10—C11—H11 | 120.906 |
| C1—C6—C5 | 120.32 (16) | C12—C11—H11 | 120.905 |
| N1—C7—C8 | 119.28 (17) | C7—C12—H12 | 120.047 |
| N1—C7—C12 | 119.89 (17) | C11—C12—H12 | 120.052 |
| C8—C7—C12 | 120.83 (16) | C13—C14—H14A | 109.475 |
| C7—C8—C9 | 119.54 (19) | C13—C14—H14B | 109.471 |
| C8—C9—C10 | 118.86 (19) | C13—C14—H14C | 109.473 |
| N3—C10—C9 | 118.49 (17) | H14A—C14—H14B | 109.467 |
| N3—C10—C11 | 118.85 (17) | H14A—C14—H14C | 109.475 |
| C9—C10—C11 | 122.65 (16) | H14B—C14—H14C | 109.467 |
| C1—N1—C7—C8 | −104.8 (2) | N1—C1—C2—C3 | −174.74 (15) |
| C1—N1—C7—C12 | 74.4 (3) | N1—C1—C6—C5 | 176.24 (15) |
| C7—N1—C1—C2 | −148.93 (15) | C2—C1—C6—C5 | −2.9 (3) |
| C7—N1—C1—C6 | 32.0 (3) | C6—C1—C2—C3 | 4.4 (3) |
| C1—N1—C13—O5 | −1.9 (3) | C1—C2—C3—C4 | −1.9 (3) |
| C1—N1—C13—C14 | 178.27 (14) | C2—C3—C4—N2 | 176.24 (16) |
| C13—N1—C1—C2 | 42.7 (3) | C2—C3—C4—C5 | −2.1 (3) |
| C13—N1—C1—C6 | −136.44 (16) | N2—C4—C5—C6 | −174.77 (16) |
| C7—N1—C13—O5 | −169.91 (16) | C3—C4—C5—C6 | 3.6 (3) |
| C7—N1—C13—C14 | 10.3 (3) | C4—C5—C6—C1 | −1.0 (3) |
| C13—N1—C7—C8 | 63.5 (3) | N1—C7—C8—C9 | −178.66 (17) |
| C13—N1—C7—C12 | −117.3 (2) | N1—C7—C12—C11 | 179.13 (17) |
| O1—N2—C4—C3 | −6.7 (3) | C8—C7—C12—C11 | −1.7 (4) |
| O1—N2—C4—C5 | 171.77 (17) | C12—C7—C8—C9 | 2.1 (4) |
| O2—N2—C4—C3 | 174.59 (18) | C7—C8—C9—C10 | −1.0 (4) |
| O2—N2—C4—C5 | −7.0 (3) | C8—C9—C10—N3 | 178.05 (19) |
| O3—N3—C10—C9 | −3.0 (3) | C8—C9—C10—C11 | −0.5 (4) |
| O3—N3—C10—C11 | 175.68 (18) | N3—C10—C11—C12 | −177.59 (18) |
| O4—N3—C10—C9 | 177.92 (19) | C9—C10—C11—C12 | 1.0 (4) |
| O4—N3—C10—C11 | −3.4 (3) | C10—C11—C12—C7 | 0.1 (4) |
| H··· | ||||
| C3—H3···O5ix | 0.95 | 2.39 | 3.183 (3) | 141 |
| C8—H8···O5viii | 0.95 | 2.34 | 3.204 (3) | 152 |
Hydrogen-bond geometry (Å, °)
|
|
| H⋯ |
|
|
|---|---|---|---|---|
| C3—H3⋯O5i | 0.95 | 2.39 | 3.183 (3) | 141 |
| C8—H8⋯O5ii | 0.95 | 2.34 | 3.204 (3) | 152 |
Symmetry codes: (i) ; (ii) .