Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801018268/ya6065sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801018268/ya6065Isup2.hkl |
CCDC reference: 177198
Key indicators
- Powder X-ray study
- T = 295 K
- Mean (C-C) = 0.006 Å
- R factor = 0.045
- wR factor = 0.060
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Data collection: local program; cell refinement: LSPAID (Visser, 1986); program(s) used to solve structure: MRIA (Zlokazov & Chernyshev, 1992); program(s) used to refine structure: MRIA; molecular graphics: PLUTON (Spek, 1992); software used to prepare material for publication: PARST (Nardelli, 1983).
C16H11N3O3 | F(000) = 608 |
Mr = 293.28 | Dx = 1.446 Mg m−3 |
Orthorhombic, P212121 | Melting point: 487 K |
a = 15.036 (5) Å | Cu Kα radiation, λ = 1.5418 Å |
b = 12.722 (4) Å | T = 295 K |
c = 7.042 (3) Å | Particle morphology: fibre-like needles |
V = 1347.1 (8) Å3 | orange-red |
Z = 4 | flat_sheet, 25 × 25 mm |
DRON-3M diffractometer (Burevestnik, Russia) | Data collection mode: reflection |
Radiation source: X-ray sealed tube | Scan method: step |
Ni filtered monochromator | 2θmin = 8.0°, 2θmax = 66.0°, 2θstep = 0.02° |
Specimen mounting: pressed as a thin layer in the specimen holder |
Refinement on Inet | 112 parameters |
Least-squares matrix: full with fixed elements per cycle | 14 restraints |
Rp = 0.045 | 0 constraints |
Rwp = 0.060 | H-atom parameters not refined |
Rexp = 0.016 | Weighting scheme based on measured s.u.'s |
3101 data points | (Δ/σ)max = 0.042 |
Excluded region(s): 66.02 - 70.0 | Background function: Chebyshev polynomial up to the 5th order |
Profile function: split-type pseudo-Voigt | Preferred orientation correction: March-Dollase (Dollase, 1986) along [001], G1 = 1.210(1) |
Experimental. specimen was rotated in its plane |
Refinement. Hydrogen atoms were placed in calculated positions. The planarity of the phenyl and nitro groups and of the naphthalene fragment was restrained. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.1068 (3) | 0.5962 (4) | 0.1680 (7) | 0.094 (2)* | |
O2 | 0.2187 (3) | 0.7735 (4) | 0.0969 (11) | 0.110 (2)* | |
O3 | 0.3150 (4) | 0.8961 (3) | 0.0785 (11) | 0.110 (2)* | |
N1 | 0.2717 (3) | 0.5780 (4) | 0.1271 (9) | 0.062 (2)* | |
N2 | 0.2677 (4) | 0.4717 (5) | 0.1146 (7) | 0.062 (2)* | |
N3 | 0.2957 (3) | 0.8031 (3) | 0.0932 (9) | 0.110 (2)* | |
C1 | 0.1843 (3) | 0.4366 (3) | 0.1272 (5) | 0.094 (2)* | |
C2 | 0.1008 (3) | 0.4962 (3) | 0.1551 (8) | 0.094 (2)* | |
C3 | 0.0164 (3) | 0.4387 (3) | 0.1684 (9) | 0.094 (2)* | |
C4 | 0.0131 (3) | 0.3350 (3) | 0.1522 (7) | 0.094 (2)* | |
C5 | 0.0869 (3) | 0.1652 (4) | 0.1082 (9) | 0.094 (2)* | |
C6 | 0.1625 (3) | 0.1050 (3) | 0.0817 (6) | 0.094 (2)* | |
C7 | 0.2468 (3) | 0.1537 (3) | 0.0677 (8) | 0.094 (2)* | |
C8 | 0.2547 (3) | 0.2622 (3) | 0.0827 (8) | 0.094 (2)* | |
C9 | 0.1782 (3) | 0.3231 (3) | 0.1123 (8) | 0.094 (2)* | |
C10 | 0.0937 (3) | 0.2751 (3) | 0.1226 (7) | 0.094 (2)* | |
C11 | 0.3558 (3) | 0.6169 (4) | 0.1309 (9) | 0.062 (2)* | |
C12 | 0.3693 (3) | 0.7258 (4) | 0.1181 (7) | 0.062 (2)* | |
C13 | 0.4559 (3) | 0.7671 (3) | 0.1258 (10) | 0.062 (2)* | |
C14 | 0.5279 (3) | 0.7012 (3) | 0.1426 (8) | 0.062 (2)* | |
C15 | 0.5144 (3) | 0.5924 (3) | 0.1549 (10) | 0.062 (2)* | |
C16 | 0.4299 (3) | 0.5506 (3) | 0.1550 (9) | 0.062 (2)* | |
H1 | 0.2236 | 0.6186 | 0.1447 | 0.074* | |
H3 | −0.0336 | 0.4839 | 0.1867 | 0.11* | |
H4 | −0.0398 | 0.2933 | 0.1590 | 0.11* | |
H5 | 0.0300 | 0.1335 | 0.1182 | 0.11* | |
H6 | 0.1593 | 0.0308 | 0.0718 | 0.11* | |
H7 | 0.2974 | 0.1108 | 0.0494 | 0.11* | |
H8 | 0.3109 | 0.2955 | 0.0750 | 0.11* | |
H13 | 0.4635 | 0.8411 | 0.1129 | 0.074* | |
H14 | 0.5870 | 0.7280 | 0.1437 | 0.074* | |
H15 | 0.5650 | 0.5479 | 0.1703 | 0.074* | |
H16 | 0.4200 | 0.4772 | 0.1688 | 0.074* |
O1—C2 | 1.279 (6) | C11—C12 | 1.403 (7) |
O2—N3 | 1.218 (6) | C11—C16 | 1.408 (6) |
O3—N3 | 1.223 (6) | C12—C13 | 1.405 (6) |
N1—N2 | 1.357 (8) | C13—C14 | 1.374 (6) |
N1—C11 | 1.358 (7) | C14—C15 | 1.402 (6) |
N2—C1 | 1.334 (8) | C15—C16 | 1.377 (6) |
N3—C12 | 1.491 (6) | N1—H1 | 0.897 |
C1—C2 | 1.480 (6) | C3—H3 | 0.955 |
C1—C9 | 1.451 (5) | C4—H4 | 0.957 |
C2—C3 | 1.468 (6) | C5—H5 | 0.949 |
C3—C4 | 1.325 (5) | C6—H6 | 0.948 |
C4—C10 | 1.447 (6) | C7—H7 | 0.945 |
C5—C6 | 1.383 (6) | C8—H8 | 0.947 |
C5—C10 | 1.406 (6) | C13—H13 | 0.953 |
C6—C7 | 1.414 (6) | C14—H14 | 0.952 |
C7—C8 | 1.390 (5) | C15—H15 | 0.955 |
C8—C9 | 1.402 (6) | C16—H16 | 0.951 |
C9—C10 | 1.412 (6) | ||
N2—N1—C11 | 113.9 (5) | N3—C12—C13 | 116.5 (4) |
N1—N2—C1 | 111.8 (5) | C12—C13—C14 | 120.3 (4) |
O2—N3—O3 | 121.8 (5) | C13—C14—C15 | 119.6 (4) |
O3—N3—C12 | 118.2 (4) | C14—C15—C16 | 121.0 (4) |
O2—N3—C12 | 120.0 (4) | C11—C16—C15 | 119.9 (4) |
N2—C1—C9 | 112.8 (4) | C11—N1—H1 | 122.5 |
N2—C1—C2 | 129.4 (5) | N2—N1—H1 | 123.2 |
C2—C1—C9 | 117.8 (3) | C2—C3—H3 | 112.9 |
O1—C2—C1 | 117.4 (4) | C4—C3—H3 | 125.6 |
C1—C2—C3 | 119.1 (4) | C3—C4—H4 | 125.4 |
O1—C2—C3 | 123.5 (4) | C10—C4—H4 | 114.3 |
C2—C3—C4 | 121.5 (4) | C10—C5—H5 | 118.9 |
C3—C4—C10 | 120.4 (4) | C6—C5—H5 | 121.1 |
C6—C5—C10 | 120.1 (4) | C7—C6—H6 | 118.5 |
C5—C6—C7 | 120.2 (4) | C5—C6—H6 | 121.3 |
C6—C7—C8 | 120.4 (4) | C8—C7—H7 | 121.0 |
C7—C8—C9 | 119.3 (4) | C6—C7—H7 | 118.6 |
C1—C9—C8 | 120.6 (4) | C7—C8—H8 | 121.1 |
C8—C9—C10 | 120.5 (4) | C9—C8—H8 | 119.6 |
C1—C9—C10 | 118.9 (4) | C12—C13—H13 | 118.5 |
C5—C10—C9 | 119.5 (4) | C14—C13—H13 | 121.1 |
C4—C10—C9 | 122.3 (4) | C13—C14—H14 | 121.2 |
C4—C10—C5 | 118.3 (4) | C15—C14—H14 | 119.2 |
N1—C11—C16 | 121.4 (4) | C14—C15—H15 | 118.5 |
N1—C11—C12 | 119.6 (5) | C16—C15—H15 | 120.4 |
C12—C11—C16 | 119.0 (4) | C15—C16—H16 | 121.6 |
N3—C12—C11 | 123.5 (4) | C11—C16—H16 | 118.5 |
C11—C12—C13 | 120.1 (4) |