3,5-Di­nitro­salicylic acid-phenazine (1/1)

In the 1:1 molecular complex of 3,5-di­nitro­salicylic acid and phenazine, C₇H₄N₂O₇·C₁₂H₈N₂, 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.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.059
• wR factor = 0.132
• Data-to-parameter ratio = 15.4

checkCIF results

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Computing details

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)

Crystal data

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) Å^3	Rhombic, yellow
Z = 4	0.36 × 0.34 × 0.26 mm
F(000) = 840

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.132	H-atom parameters constrained
S = 0.92	w = 1/[σ^2(Fo^2) + (0.0573P)^2] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

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···O1^i	0.93	2.66	3.550 (4)	161
C11—H11A···O7^i	0.93	2.62	3.524 (3)	163
C13—H13A···O4^ii	0.93	2.49	3.332 (4)	151
C14—H14A···O3^ii	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.