In the 1:1 molecular complex of 3,5-dinitrosalicylic acid and phenazine, C
7H
4N
2O
7·C
12H
8N
2, the carboxylic acid group forms an O—H
N hydrogen bond to only one of the two heterocyclic N atoms. The structure is also stabilized extensively by C—H
O hydrogen bonds.
Supporting information
CCDC reference: 193751
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.059
- wR factor = 0.132
- Data-to-parameter ratio = 15.4
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Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: Xtal3.5 (Hall et al., 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLUTON (Spek, 2000); software used to prepare material for publication: SHELXL97.
3,5-Dinitrosalicylic acid–phenazine (1/1)
top
Crystal data top
C7H4N2O7·C12H8N2 | Dx = 1.556 Mg m−3 |
Mr = 408.33 | Melting point: 471 K K |
Monoclinic, P21/a | Mo Kα radiation, λ = 0.71073 Å |
a = 14.8002 (15) Å | Cell parameters from 25 reflections |
b = 7.4029 (16) Å | θ = 5–12° |
c = 16.0091 (16) Å | µ = 0.12 mm−1 |
β = 96.395 (8)° | T = 293 K |
V = 1743.1 (5) Å3 | Rhombic, yellow |
Z = 4 | 0.36 × 0.34 × 0.26 mm |
F(000) = 840 | |
Data collection top
Enraf-Nonius CAD-4 diffractometer | 1930 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.056 |
Graphite monochromator | θmax = 28.0°, θmin = 1.5° |
Detector resolution: none pixels mm-1 | h = 0→19 |
w scans | k = −9→9 |
8396 measured reflections | l = −21→21 |
4202 independent reflections | |
Refinement top
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)] = 0.059 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.132 | H-atom parameters constrained |
S = 0.92 | w = 1/[σ2(Fo2) + (0.0573P)2] where P = (Fo2 + 2Fc2)/3 |
4202 reflections | (Δ/σ)max = 0.001 |
273 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O3 | 0.98785 (15) | 0.2881 (3) | 0.46742 (11) | 0.0596 (5) | |
H3A | 0.9345 | 0.2738 | 0.4485 | 0.15 (2)* | |
O1 | 0.85113 (11) | 0.4312 (3) | 0.24144 (11) | 0.0548 (5) | |
H1A | 0.7969 | 0.4057 | 0.2360 | 0.123 (15)* | |
C1 | 0.98634 (14) | 0.4161 (3) | 0.33156 (14) | 0.0373 (6) | |
O7 | 1.12736 (12) | 0.6538 (3) | 0.15680 (12) | 0.0707 (6) | |
C4 | 1.17209 (15) | 0.4786 (3) | 0.36319 (15) | 0.0418 (6) | |
H4A | 1.2342 | 0.5011 | 0.3733 | 0.050* | |
C5 | 1.12445 (15) | 0.5258 (3) | 0.28740 (14) | 0.0378 (6) | |
O2 | 0.84471 (11) | 0.3109 (3) | 0.36772 (12) | 0.0628 (6) | |
C2 | 1.03242 (16) | 0.3663 (4) | 0.40997 (15) | 0.0426 (6) | |
C3 | 1.12664 (16) | 0.3978 (4) | 0.42353 (14) | 0.0425 (6) | |
N1 | 1.18059 (18) | 0.3459 (4) | 0.50175 (14) | 0.0647 (7) | |
C7 | 0.88712 (16) | 0.3817 (4) | 0.31434 (16) | 0.0442 (6) | |
C6 | 1.03250 (14) | 0.4944 (3) | 0.27131 (14) | 0.0381 (6) | |
H6A | 1.0017 | 0.5262 | 0.2196 | 0.046* | |
O6 | 1.25203 (12) | 0.6450 (3) | 0.23814 (13) | 0.0791 (7) | |
O4 | 1.14448 (18) | 0.2745 (5) | 0.55636 (17) | 0.1283 (12) | |
N2 | 1.17134 (14) | 0.6125 (3) | 0.22288 (14) | 0.0483 (6) | |
O5 | 1.26032 (15) | 0.3839 (4) | 0.50998 (13) | 0.0989 (9) | |
N3 | 0.68410 (12) | 0.3730 (3) | 0.18994 (12) | 0.0384 (5) | |
N4 | 0.50802 (13) | 0.3570 (3) | 0.10512 (13) | 0.0518 (6) | |
C17 | 0.57955 (17) | 0.2987 (4) | 0.06918 (16) | 0.0501 (7) | |
C19 | 0.61285 (15) | 0.4325 (3) | 0.22716 (14) | 0.0375 (6) | |
C8 | 0.74374 (19) | 0.2489 (4) | 0.06907 (18) | 0.0551 (8) | |
H8A | 0.8027 | 0.2529 | 0.0961 | 0.066* | |
C16 | 0.67015 (16) | 0.3065 (3) | 0.11139 (15) | 0.0400 (6) | |
C18 | 0.52348 (15) | 0.4265 (4) | 0.18291 (16) | 0.0411 (6) | |
C12 | 0.45071 (16) | 0.4977 (4) | 0.22232 (18) | 0.0524 (7) | |
H12A | 0.3924 | 0.4986 | 0.1939 | 0.063* | |
C14 | 0.55303 (18) | 0.5658 (4) | 0.34546 (17) | 0.0513 (7) | |
H14A | 0.5613 | 0.6108 | 0.4000 | 0.062* | |
C13 | 0.46521 (18) | 0.5644 (4) | 0.30092 (19) | 0.0547 (7) | |
H13A | 0.4165 | 0.6103 | 0.3263 | 0.066* | |
C15 | 0.62562 (16) | 0.5021 (3) | 0.30947 (15) | 0.0438 (6) | |
H15A | 0.6834 | 0.5044 | 0.3390 | 0.053* | |
C10 | 0.6403 (3) | 0.1767 (5) | −0.05201 (19) | 0.0782 (10) | |
H10A | 0.6315 | 0.1324 | −0.1067 | 0.094* | |
C11 | 0.5678 (2) | 0.2288 (5) | −0.01391 (18) | 0.0691 (9) | |
H11A | 0.5097 | 0.2190 | −0.0423 | 0.083* | |
C9 | 0.7283 (2) | 0.1879 (4) | −0.01067 (19) | 0.0675 (9) | |
H9A | 0.7772 | 0.1528 | −0.0386 | 0.081* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O3 | 0.0645 (13) | 0.0721 (15) | 0.0437 (10) | 0.0000 (11) | 0.0119 (10) | 0.0099 (10) |
O1 | 0.0310 (9) | 0.0765 (15) | 0.0560 (11) | −0.0037 (9) | 0.0016 (8) | 0.0083 (10) |
C1 | 0.0332 (12) | 0.0394 (15) | 0.0398 (13) | 0.0008 (11) | 0.0059 (10) | −0.0035 (12) |
O7 | 0.0546 (11) | 0.1053 (19) | 0.0518 (12) | −0.0117 (12) | 0.0043 (10) | 0.0193 (13) |
C4 | 0.0319 (12) | 0.0469 (17) | 0.0448 (14) | 0.0043 (12) | −0.0031 (11) | −0.0126 (13) |
C5 | 0.0317 (12) | 0.0414 (16) | 0.0406 (13) | 0.0020 (11) | 0.0064 (10) | −0.0050 (12) |
O2 | 0.0448 (10) | 0.0808 (15) | 0.0653 (12) | −0.0077 (10) | 0.0176 (9) | 0.0141 (12) |
C2 | 0.0484 (14) | 0.0426 (16) | 0.0371 (13) | 0.0024 (13) | 0.0070 (11) | −0.0027 (12) |
C3 | 0.0452 (14) | 0.0471 (17) | 0.0335 (13) | 0.0130 (12) | −0.0031 (11) | −0.0072 (12) |
N1 | 0.0628 (16) | 0.087 (2) | 0.0410 (14) | 0.0149 (16) | −0.0091 (12) | −0.0027 (14) |
C7 | 0.0377 (13) | 0.0472 (18) | 0.0483 (15) | 0.0007 (12) | 0.0067 (12) | −0.0003 (13) |
C6 | 0.0322 (12) | 0.0437 (15) | 0.0376 (13) | 0.0053 (11) | −0.0002 (10) | −0.0038 (12) |
O6 | 0.0313 (10) | 0.121 (2) | 0.0867 (14) | −0.0119 (12) | 0.0122 (9) | 0.0133 (14) |
O4 | 0.1038 (19) | 0.195 (3) | 0.0799 (17) | −0.012 (2) | −0.0173 (15) | 0.075 (2) |
N2 | 0.0344 (12) | 0.0561 (16) | 0.0556 (14) | −0.0010 (11) | 0.0111 (10) | −0.0043 (12) |
O5 | 0.0579 (14) | 0.175 (3) | 0.0575 (13) | 0.0134 (17) | −0.0212 (11) | −0.0055 (15) |
N3 | 0.0316 (10) | 0.0422 (13) | 0.0412 (11) | −0.0023 (9) | 0.0029 (8) | 0.0015 (10) |
N4 | 0.0438 (12) | 0.0532 (15) | 0.0556 (14) | 0.0016 (11) | −0.0074 (10) | −0.0032 (12) |
C17 | 0.0526 (15) | 0.0496 (18) | 0.0460 (15) | 0.0040 (14) | −0.0038 (13) | −0.0023 (14) |
C19 | 0.0342 (12) | 0.0359 (15) | 0.0416 (13) | −0.0053 (11) | 0.0011 (10) | 0.0033 (12) |
C8 | 0.0560 (16) | 0.0513 (19) | 0.0595 (18) | 0.0019 (14) | 0.0128 (14) | −0.0015 (15) |
C16 | 0.0442 (14) | 0.0337 (15) | 0.0423 (14) | 0.0007 (12) | 0.0058 (11) | 0.0020 (12) |
C18 | 0.0349 (12) | 0.0378 (15) | 0.0501 (15) | −0.0004 (12) | 0.0025 (11) | −0.0010 (13) |
C12 | 0.0339 (14) | 0.0510 (18) | 0.0723 (19) | 0.0029 (13) | 0.0055 (13) | −0.0033 (16) |
C14 | 0.0596 (17) | 0.0469 (18) | 0.0492 (15) | −0.0031 (14) | 0.0141 (13) | −0.0044 (14) |
C13 | 0.0452 (15) | 0.0495 (19) | 0.073 (2) | 0.0059 (14) | 0.0213 (14) | −0.0042 (16) |
C15 | 0.0429 (14) | 0.0475 (17) | 0.0398 (14) | −0.0032 (13) | −0.0003 (11) | 0.0040 (13) |
C10 | 0.108 (3) | 0.077 (3) | 0.0496 (18) | 0.010 (2) | 0.0066 (19) | −0.0204 (18) |
C11 | 0.079 (2) | 0.072 (2) | 0.0523 (18) | 0.0058 (18) | −0.0148 (16) | −0.0144 (16) |
C9 | 0.088 (2) | 0.061 (2) | 0.0583 (19) | 0.0057 (18) | 0.0260 (18) | −0.0071 (17) |
Geometric parameters (Å, º) top
O3—C2 | 1.323 (3) | N4—C17 | 1.332 (3) |
O3—H3A | 0.8200 | N4—C18 | 1.343 (3) |
O1—C7 | 1.281 (3) | C17—C11 | 1.420 (4) |
O1—H1A | 0.8200 | C17—C16 | 1.434 (3) |
C1—C6 | 1.371 (3) | C19—C15 | 1.408 (3) |
C1—C2 | 1.409 (3) | C19—C18 | 1.430 (3) |
C1—C7 | 1.486 (3) | C8—C9 | 1.349 (4) |
O7—N2 | 1.218 (3) | C8—C16 | 1.411 (3) |
C4—C3 | 1.374 (3) | C8—H8A | 0.9300 |
C4—C5 | 1.379 (3) | C18—C12 | 1.410 (3) |
C4—H4A | 0.9300 | C12—C13 | 1.346 (4) |
C5—C6 | 1.376 (3) | C12—H12A | 0.9300 |
C5—N2 | 1.456 (3) | C14—C15 | 1.359 (3) |
O2—C7 | 1.232 (3) | C14—C13 | 1.411 (4) |
C2—C3 | 1.407 (3) | C14—H14A | 0.9300 |
C3—N1 | 1.460 (3) | C13—H13A | 0.9300 |
N1—O4 | 1.197 (3) | C15—H15A | 0.9300 |
N1—O5 | 1.206 (3) | C10—C11 | 1.348 (4) |
C6—H6A | 0.9300 | C10—C9 | 1.397 (4) |
O6—N2 | 1.216 (2) | C10—H10A | 0.9300 |
N3—C19 | 1.342 (3) | C11—H11A | 0.9300 |
N3—C16 | 1.345 (3) | C9—H9A | 0.9300 |
| | | |
C2—O3—H3A | 109.5 | N3—C19—C15 | 120.4 (2) |
C7—O1—H1A | 109.5 | N3—C19—C18 | 119.9 (2) |
C6—C1—C2 | 120.5 (2) | C15—C19—C18 | 119.7 (2) |
C6—C1—C7 | 120.1 (2) | C9—C8—C16 | 119.8 (3) |
C2—C1—C7 | 119.4 (2) | C9—C8—H8A | 120.1 |
C3—C4—C5 | 119.1 (2) | C16—C8—H8A | 120.1 |
C3—C4—H4A | 120.4 | N3—C16—C8 | 120.9 (2) |
C5—C4—H4A | 120.4 | N3—C16—C17 | 119.6 (2) |
C6—C5—C4 | 121.3 (2) | C8—C16—C17 | 119.5 (2) |
C6—C5—N2 | 118.8 (2) | N4—C18—C12 | 119.9 (2) |
C4—C5—N2 | 119.9 (2) | N4—C18—C19 | 121.6 (2) |
O3—C2—C3 | 121.8 (2) | C12—C18—C19 | 118.5 (2) |
O3—C2—C1 | 120.3 (2) | C13—C12—C18 | 120.3 (2) |
C3—C2—C1 | 117.9 (2) | C13—C12—H12A | 119.8 |
C4—C3—C2 | 121.2 (2) | C18—C12—H12A | 119.8 |
C4—C3—N1 | 117.0 (2) | C15—C14—C13 | 120.7 (2) |
C2—C3—N1 | 121.8 (2) | C15—C14—H14A | 119.7 |
O4—N1—O5 | 122.3 (3) | C13—C14—H14A | 119.7 |
O4—N1—C3 | 119.8 (3) | C12—C13—C14 | 121.1 (2) |
O5—N1—C3 | 117.9 (3) | C12—C13—H13A | 119.4 |
O2—C7—O1 | 124.1 (2) | C14—C13—H13A | 119.4 |
O2—C7—C1 | 120.9 (2) | C14—C15—C19 | 119.6 (2) |
O1—C7—C1 | 115.0 (2) | C14—C15—H15A | 120.2 |
C1—C6—C5 | 120.0 (2) | C19—C15—H15A | 120.2 |
C1—C6—H6A | 120.0 | C11—C10—C9 | 121.0 (3) |
C5—C6—H6A | 120.0 | C11—C10—H10A | 119.5 |
O6—N2—O7 | 122.9 (2) | C9—C10—H10A | 119.5 |
O6—N2—C5 | 118.7 (2) | C10—C11—C17 | 120.5 (3) |
O7—N2—C5 | 118.4 (2) | C10—C11—H11A | 119.7 |
C19—N3—C16 | 119.27 (19) | C17—C11—H11A | 119.7 |
C17—N4—C18 | 117.6 (2) | C8—C9—C10 | 121.3 (3) |
N4—C17—C11 | 120.2 (2) | C8—C9—H9A | 119.4 |
N4—C17—C16 | 122.0 (2) | C10—C9—H9A | 119.4 |
C11—C17—C16 | 117.8 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···N3 | 0.82 | 1.76 | 2.554 (3) | 161 |
C10—H10A···O1i | 0.93 | 2.66 | 3.550 (4) | 161 |
C11—H11A···O7i | 0.93 | 2.62 | 3.524 (3) | 163 |
C13—H13A···O4ii | 0.93 | 2.49 | 3.332 (4) | 151 |
C14—H14A···O3ii | 0.93 | 2.66 | 3.529 (3) | 155 |
C15—H15A···O2 | 0.93 | 2.78 | 3.566 (3) | 143 |
Symmetry codes: (i) −x+3/2, y−1/2, −z; (ii) −x+3/2, y+1/2, −z+1. |