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In the 1:1 cocrystal of phenazine with 2,6-dihydroxybenzoic acid, C
12H
8N
2·C
7H
6O
4, the two symmetry-independent molecules of phenazine are located on inversion centres. The carboxyl group of the acid assumes the
syn conformation. One of the phenazine molecules is connected to two acid molecules
via strong O—H
N interactions, forming a discrete hydrogen-bonded assembly. The phenazine molecules are arranged into infinite columns by π–π stacking interactions, and the carboxylic acid molecules, which are strongly tilted relative to the heterocyclic molecules, occupy channels formed between these columns.
Supporting information
CCDC reference: 636119
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.003 Å
- R factor = 0.048
- wR factor = 0.112
- Data-to-parameter ratio = 11.2
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT355_ALERT_3_B Long O-H Bond (0.82A) O4 - H4O ... 1.09 Ang.
Alert level C
PLAT480_ALERT_4_C Long H...A H-Bond Reported H4B .. N1A .. 2.74 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H3A .. O2 .. 2.64 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H5B .. O2 .. 2.68 Ang.
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
3 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
3 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: CrysAlis CCD (Oxford Diffraction, 2004); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Stereochemical Workstation Operation Manual (Siemens, 1989) and
Mercury (Version 1.4; Macrae et al., 2006); software used to prepare material for publication: SHELXL97.
Phenazine–2,6-dihydroxybenzoic acid (1/1)
top
Crystal data top
C12H8N2·C7H6O4 | F(000) = 1392 |
Mr = 334.32 | Dx = 1.461 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 1855 reflections |
a = 16.5921 (18) Å | θ = 4–25° |
b = 7.4480 (7) Å | µ = 0.10 mm−1 |
c = 25.297 (2) Å | T = 100 K |
β = 103.57 (2)° | Block, yellow |
V = 3038.9 (6) Å3 | 0.15 × 0.12 × 0.09 mm |
Z = 8 | |
Data collection top
Kuma KM4 κ-geometry CCD area-detector diffractometer | 1876 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.038 |
Graphite monochromator | θmax = 25.0°, θmin = 3.6° |
ω scans | h = −15→19 |
7257 measured reflections | k = −8→8 |
2667 independent reflections | l = −28→30 |
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)] = 0.048 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.113 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0534P)2 + 1.0575P] where P = (Fo2 + 2Fc2)/3 |
2667 reflections | (Δ/σ)max < 0.001 |
238 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.21 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 | |
C1 | 0.54456 (13) | 0.5591 (3) | 0.69372 (8) | 0.0186 (5) | |
C2 | 0.60228 (13) | 0.6779 (3) | 0.72671 (9) | 0.0193 (5) | |
C3 | 0.67036 (13) | 0.6123 (3) | 0.76457 (9) | 0.0221 (5) | |
H3 | 0.7087 | 0.6928 | 0.7863 | 0.026* | |
C4 | 0.68188 (14) | 0.4285 (3) | 0.77042 (9) | 0.0225 (5) | |
H4 | 0.7290 | 0.3840 | 0.7960 | 0.027* | |
C5 | 0.62633 (14) | 0.3081 (3) | 0.73978 (9) | 0.0232 (5) | |
H5 | 0.6352 | 0.1825 | 0.7446 | 0.028* | |
C6 | 0.55765 (13) | 0.3722 (3) | 0.70204 (9) | 0.0199 (5) | |
C7 | 0.47677 (14) | 0.6363 (3) | 0.65202 (9) | 0.0217 (5) | |
O1 | 0.59442 (10) | 0.8587 (2) | 0.72250 (7) | 0.0275 (4) | |
H1O | 0.5469 (18) | 0.875 (4) | 0.6966 (12) | 0.052 (9)* | |
O2 | 0.50553 (10) | 0.2462 (2) | 0.67427 (7) | 0.0259 (4) | |
H2O | 0.4614 (18) | 0.298 (4) | 0.6525 (11) | 0.048 (9)* | |
O3 | 0.46821 (10) | 0.7980 (2) | 0.64386 (7) | 0.0335 (5) | |
O4 | 0.42443 (9) | 0.5186 (2) | 0.62198 (6) | 0.0253 (4) | |
H4O | 0.375 (2) | 0.588 (5) | 0.5935 (13) | 0.076 (10)* | |
N1A | 0.66289 (11) | 0.7762 (2) | 0.49310 (7) | 0.0204 (4) | |
C2A | 0.70315 (13) | 0.8265 (3) | 0.45475 (8) | 0.0177 (5) | |
C3A | 0.65756 (14) | 0.9112 (3) | 0.40653 (9) | 0.0217 (5) | |
H3A | 0.5999 | 0.9322 | 0.4020 | 0.026* | |
C4A | 0.69551 (14) | 0.9622 (3) | 0.36710 (9) | 0.0228 (5) | |
H4A | 0.6641 | 1.0170 | 0.3349 | 0.027* | |
C5A | 0.71773 (14) | 0.5656 (3) | 0.62654 (9) | 0.0241 (5) | |
H5A | 0.6919 | 0.5294 | 0.6546 | 0.029* | |
C6A | 0.67170 (14) | 0.6434 (3) | 0.58069 (9) | 0.0237 (5) | |
H6A | 0.6138 | 0.6600 | 0.5768 | 0.028* | |
C7A | 0.70954 (13) | 0.7004 (3) | 0.53836 (9) | 0.0188 (5) | |
N1B | 0.30893 (11) | 0.6689 (2) | 0.54264 (7) | 0.0195 (4) | |
C2B | 0.33163 (13) | 0.7384 (3) | 0.49899 (8) | 0.0189 (5) | |
C3B | 0.41567 (14) | 0.7319 (3) | 0.49590 (9) | 0.0267 (6) | |
H3B | 0.4560 | 0.6776 | 0.5243 | 0.032* | |
C4B | 0.43866 (15) | 0.8033 (3) | 0.45220 (10) | 0.0311 (6) | |
H4B | 0.4953 | 0.8001 | 0.4506 | 0.037* | |
C5B | 0.12074 (15) | 0.6174 (3) | 0.59110 (10) | 0.0281 (6) | |
H5B | 0.1034 | 0.5698 | 0.6215 | 0.034* | |
C6B | 0.20203 (14) | 0.6086 (3) | 0.58971 (9) | 0.0235 (5) | |
H6B | 0.2412 | 0.5549 | 0.6189 | 0.028* | |
C7B | 0.22833 (13) | 0.6801 (3) | 0.54440 (8) | 0.0181 (5) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0176 (11) | 0.0225 (13) | 0.0167 (11) | 0.0014 (9) | 0.0060 (9) | 0.0000 (9) |
C2 | 0.0228 (12) | 0.0189 (13) | 0.0189 (12) | 0.0004 (10) | 0.0104 (10) | 0.0005 (10) |
C3 | 0.0217 (12) | 0.0242 (13) | 0.0187 (12) | −0.0016 (10) | 0.0015 (10) | −0.0040 (10) |
C4 | 0.0223 (12) | 0.0254 (13) | 0.0184 (12) | 0.0019 (10) | 0.0019 (9) | 0.0009 (10) |
C5 | 0.0260 (13) | 0.0197 (12) | 0.0235 (12) | 0.0047 (10) | 0.0052 (10) | 0.0012 (10) |
C6 | 0.0171 (12) | 0.0235 (13) | 0.0205 (12) | −0.0024 (10) | 0.0073 (10) | −0.0031 (10) |
C7 | 0.0192 (12) | 0.0245 (13) | 0.0220 (12) | −0.0005 (10) | 0.0062 (9) | −0.0029 (10) |
O1 | 0.0284 (9) | 0.0173 (9) | 0.0329 (10) | −0.0005 (7) | −0.0004 (8) | 0.0003 (7) |
O2 | 0.0227 (9) | 0.0231 (9) | 0.0289 (9) | −0.0019 (7) | 0.0000 (7) | −0.0020 (8) |
O3 | 0.0321 (10) | 0.0226 (10) | 0.0391 (10) | 0.0049 (8) | −0.0047 (8) | 0.0022 (8) |
O4 | 0.0212 (8) | 0.0263 (9) | 0.0250 (9) | 0.0005 (7) | −0.0013 (7) | −0.0016 (7) |
N1A | 0.0201 (10) | 0.0190 (10) | 0.0216 (10) | −0.0001 (8) | 0.0035 (8) | −0.0010 (8) |
C2A | 0.0201 (11) | 0.0142 (11) | 0.0188 (12) | −0.0018 (9) | 0.0042 (9) | −0.0033 (9) |
C3A | 0.0208 (12) | 0.0197 (12) | 0.0232 (12) | −0.0006 (10) | 0.0024 (10) | −0.0032 (10) |
C4A | 0.0280 (13) | 0.0191 (13) | 0.0190 (12) | −0.0006 (10) | 0.0011 (10) | 0.0002 (10) |
C5A | 0.0296 (14) | 0.0219 (13) | 0.0222 (12) | −0.0005 (10) | 0.0086 (10) | −0.0015 (10) |
C6A | 0.0208 (12) | 0.0251 (13) | 0.0268 (13) | −0.0013 (10) | 0.0088 (10) | −0.0025 (10) |
C7A | 0.0209 (12) | 0.0136 (11) | 0.0212 (12) | −0.0008 (9) | 0.0035 (10) | −0.0040 (9) |
N1B | 0.0205 (10) | 0.0193 (10) | 0.0180 (10) | −0.0013 (8) | 0.0029 (8) | −0.0032 (8) |
C2B | 0.0201 (12) | 0.0194 (12) | 0.0168 (11) | −0.0012 (9) | 0.0034 (9) | −0.0047 (9) |
C3B | 0.0193 (12) | 0.0339 (15) | 0.0263 (13) | −0.0007 (11) | 0.0040 (10) | −0.0016 (11) |
C4B | 0.0206 (13) | 0.0382 (16) | 0.0366 (15) | −0.0041 (11) | 0.0107 (11) | −0.0057 (12) |
C5B | 0.0318 (14) | 0.0277 (14) | 0.0279 (13) | −0.0076 (11) | 0.0134 (11) | −0.0033 (11) |
C6B | 0.0310 (13) | 0.0187 (12) | 0.0199 (12) | −0.0019 (10) | 0.0044 (10) | −0.0021 (10) |
C7B | 0.0195 (12) | 0.0175 (12) | 0.0168 (11) | −0.0027 (9) | 0.0036 (9) | −0.0043 (9) |
Geometric parameters (Å, º) top
C1—C6 | 1.417 (3) | C3A—C4A | 1.353 (3) |
C1—C2 | 1.422 (3) | C3A—H3A | 0.9500 |
C1—C7 | 1.467 (3) | C4A—C5Ai | 1.425 (3) |
C2—O1 | 1.355 (3) | C4A—H4A | 0.9500 |
C2—C3 | 1.387 (3) | C5A—C6A | 1.360 (3) |
C3—C4 | 1.386 (3) | C5A—H5A | 0.9500 |
C3—H3 | 0.9500 | C6A—C7A | 1.427 (3) |
C4—C5 | 1.385 (3) | C6A—H6A | 0.9500 |
C4—H4 | 0.9500 | N1B—C2B | 1.351 (3) |
C5—C6 | 1.389 (3) | N1B—C7B | 1.351 (3) |
C5—H5 | 0.9500 | C2B—C3B | 1.416 (3) |
C6—O2 | 1.355 (3) | C2B—C7Bii | 1.432 (3) |
C7—O3 | 1.225 (3) | C3B—C4B | 1.360 (3) |
C7—O4 | 1.338 (3) | C3B—H3B | 0.9500 |
O1—H1O | 0.91 (3) | C4B—C5Bii | 1.419 (3) |
O2—H2O | 0.89 (3) | C4B—H4B | 0.9500 |
O4—H4O | 1.09 (3) | C5B—C6B | 1.359 (3) |
N1A—C7A | 1.347 (3) | C5B—H5B | 0.9500 |
N1A—C2A | 1.353 (3) | C6B—C7B | 1.422 (3) |
C2A—C3A | 1.423 (3) | C6B—H6B | 0.9500 |
C2A—C7Ai | 1.432 (3) | | |
| | | |
C6—C1—C2 | 117.73 (19) | C3A—C4A—C5Ai | 120.6 (2) |
C6—C1—C7 | 123.8 (2) | C3A—C4A—H4A | 119.7 |
C2—C1—C7 | 118.4 (2) | C5Ai—C4A—H4A | 119.7 |
O1—C2—C3 | 116.9 (2) | C6A—C5A—C4Ai | 120.6 (2) |
O1—C2—C1 | 122.21 (19) | C6A—C5A—H5A | 119.7 |
C3—C2—C1 | 120.9 (2) | C4Ai—C5A—H5A | 119.7 |
C4—C3—C2 | 119.4 (2) | C5A—C6A—C7A | 120.6 (2) |
C4—C3—H3 | 120.3 | C5A—C6A—H6A | 119.7 |
C2—C3—H3 | 120.3 | C7A—C6A—H6A | 119.7 |
C5—C4—C3 | 121.5 (2) | N1A—C7A—C6A | 119.8 (2) |
C5—C4—H4 | 119.2 | N1A—C7A—C2Ai | 121.7 (2) |
C3—C4—H4 | 119.2 | C6A—C7A—C2Ai | 118.5 (2) |
C4—C5—C6 | 119.5 (2) | C2B—N1B—C7B | 118.13 (18) |
C4—C5—H5 | 120.2 | N1B—C2B—C3B | 120.0 (2) |
C6—C5—H5 | 120.2 | N1B—C2B—C7Bii | 120.81 (19) |
O2—C6—C5 | 116.0 (2) | C3B—C2B—C7Bii | 119.2 (2) |
O2—C6—C1 | 123.12 (19) | C4B—C3B—C2B | 120.0 (2) |
C5—C6—C1 | 120.8 (2) | C4B—C3B—H3B | 120.0 |
O3—C7—O4 | 121.0 (2) | C2B—C3B—H3B | 120.0 |
O3—C7—C1 | 123.1 (2) | C3B—C4B—C5Bii | 120.9 (2) |
O4—C7—C1 | 116.0 (2) | C3B—C4B—H4B | 119.5 |
C2—O1—H1O | 104 (2) | C5Bii—C4B—H4B | 119.5 |
C6—O2—H2O | 110.6 (18) | C6B—C5B—C4Bii | 120.9 (2) |
C7—O4—H4O | 110.7 (18) | C6B—C5B—H5B | 119.5 |
C7A—N1A—C2A | 116.34 (19) | C4Bii—C5B—H5B | 119.5 |
N1A—C2A—C3A | 119.0 (2) | C5B—C6B—C7B | 119.8 (2) |
N1A—C2A—C7Ai | 121.98 (19) | C5B—C6B—H6B | 120.1 |
C3A—C2A—C7Ai | 119.0 (2) | C7B—C6B—H6B | 120.1 |
C4A—C3A—C2A | 120.7 (2) | N1B—C7B—C6B | 119.78 (19) |
C4A—C3A—H3A | 119.6 | N1B—C7B—C2Bii | 121.06 (19) |
C2A—C3A—H3A | 119.6 | C6B—C7B—C2Bii | 119.2 (2) |
Symmetry codes: (i) −x+3/2, −y+3/2, −z+1; (ii) −x+1/2, −y+3/2, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2O···O4 | 0.89 (3) | 1.86 (3) | 2.616 (2) | 141 (3) |
O1—H1O···O3 | 0.91 (3) | 1.73 (3) | 2.568 (2) | 152 (3) |
O4—H4O···N1B | 1.09 (3) | 1.60 (3) | 2.674 (2) | 168 (3) |
C4B—H4B···N1A | 0.95 | 2.74 | 3.626 (3) | 155 |
C3A—H3A···O3iii | 0.95 | 2.46 | 3.070 (3) | 122 |
C3A—H3A···O2iv | 0.95 | 2.64 | 3.206 (3) | 119 |
C5—H5···O1v | 0.95 | 2.53 | 3.401 (3) | 152 |
C5B—H5B···O2vi | 0.95 | 2.68 | 3.300 (3) | 124 |
Symmetry codes: (iii) −x+1, −y+2, −z+1; (iv) −x+1, −y+1, −z+1; (v) x, y−1, z; (vi) x−1/2, y+1/2, z. |
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