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In the 1:1 cocrystal of phenazine with 2,6-dihydroxy­benzoic acid, C12H8N2·C7H6O4, 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807001195/at2202sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807001195/at2202Isup2.hkl
Contains datablock I

CCDC reference: 636119

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](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

Computing details top

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·C7H6O4F(000) = 1392
Mr = 334.32Dx = 1.461 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 1855 reflections
a = 16.5921 (18) Åθ = 4–25°
b = 7.4480 (7) ŵ = 0.10 mm1
c = 25.297 (2) ÅT = 100 K
β = 103.57 (2)°Block, yellow
V = 3038.9 (6) Å30.15 × 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 tubeRint = 0.038
Graphite monochromatorθmax = 25.0°, θmin = 3.6°
ω scansh = 1519
7257 measured reflectionsk = 88
2667 independent reflectionsl = 2830
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: difference Fourier map
wR(F2) = 0.113H 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 parametersΔρmax = 0.22 e Å3
0 restraintsΔρmin = 0.21 e Å3
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
xyzUiso*/Ueq
C10.54456 (13)0.5591 (3)0.69372 (8)0.0186 (5)
C20.60228 (13)0.6779 (3)0.72671 (9)0.0193 (5)
C30.67036 (13)0.6123 (3)0.76457 (9)0.0221 (5)
H30.70870.69280.78630.026*
C40.68188 (14)0.4285 (3)0.77042 (9)0.0225 (5)
H40.72900.38400.79600.027*
C50.62633 (14)0.3081 (3)0.73978 (9)0.0232 (5)
H50.63520.18250.74460.028*
C60.55765 (13)0.3722 (3)0.70204 (9)0.0199 (5)
C70.47677 (14)0.6363 (3)0.65202 (9)0.0217 (5)
O10.59442 (10)0.8587 (2)0.72250 (7)0.0275 (4)
H1O0.5469 (18)0.875 (4)0.6966 (12)0.052 (9)*
O20.50553 (10)0.2462 (2)0.67427 (7)0.0259 (4)
H2O0.4614 (18)0.298 (4)0.6525 (11)0.048 (9)*
O30.46821 (10)0.7980 (2)0.64386 (7)0.0335 (5)
O40.42443 (9)0.5186 (2)0.62198 (6)0.0253 (4)
H4O0.375 (2)0.588 (5)0.5935 (13)0.076 (10)*
N1A0.66289 (11)0.7762 (2)0.49310 (7)0.0204 (4)
C2A0.70315 (13)0.8265 (3)0.45475 (8)0.0177 (5)
C3A0.65756 (14)0.9112 (3)0.40653 (9)0.0217 (5)
H3A0.59990.93220.40200.026*
C4A0.69551 (14)0.9622 (3)0.36710 (9)0.0228 (5)
H4A0.66411.01700.33490.027*
C5A0.71773 (14)0.5656 (3)0.62654 (9)0.0241 (5)
H5A0.69190.52940.65460.029*
C6A0.67170 (14)0.6434 (3)0.58069 (9)0.0237 (5)
H6A0.61380.66000.57680.028*
C7A0.70954 (13)0.7004 (3)0.53836 (9)0.0188 (5)
N1B0.30893 (11)0.6689 (2)0.54264 (7)0.0195 (4)
C2B0.33163 (13)0.7384 (3)0.49899 (8)0.0189 (5)
C3B0.41567 (14)0.7319 (3)0.49590 (9)0.0267 (6)
H3B0.45600.67760.52430.032*
C4B0.43866 (15)0.8033 (3)0.45220 (10)0.0311 (6)
H4B0.49530.80010.45060.037*
C5B0.12074 (15)0.6174 (3)0.59110 (10)0.0281 (6)
H5B0.10340.56980.62150.034*
C6B0.20203 (14)0.6086 (3)0.58971 (9)0.0235 (5)
H6B0.24120.55490.61890.028*
C7B0.22833 (13)0.6801 (3)0.54440 (8)0.0181 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0176 (11)0.0225 (13)0.0167 (11)0.0014 (9)0.0060 (9)0.0000 (9)
C20.0228 (12)0.0189 (13)0.0189 (12)0.0004 (10)0.0104 (10)0.0005 (10)
C30.0217 (12)0.0242 (13)0.0187 (12)0.0016 (10)0.0015 (10)0.0040 (10)
C40.0223 (12)0.0254 (13)0.0184 (12)0.0019 (10)0.0019 (9)0.0009 (10)
C50.0260 (13)0.0197 (12)0.0235 (12)0.0047 (10)0.0052 (10)0.0012 (10)
C60.0171 (12)0.0235 (13)0.0205 (12)0.0024 (10)0.0073 (10)0.0031 (10)
C70.0192 (12)0.0245 (13)0.0220 (12)0.0005 (10)0.0062 (9)0.0029 (10)
O10.0284 (9)0.0173 (9)0.0329 (10)0.0005 (7)0.0004 (8)0.0003 (7)
O20.0227 (9)0.0231 (9)0.0289 (9)0.0019 (7)0.0000 (7)0.0020 (8)
O30.0321 (10)0.0226 (10)0.0391 (10)0.0049 (8)0.0047 (8)0.0022 (8)
O40.0212 (8)0.0263 (9)0.0250 (9)0.0005 (7)0.0013 (7)0.0016 (7)
N1A0.0201 (10)0.0190 (10)0.0216 (10)0.0001 (8)0.0035 (8)0.0010 (8)
C2A0.0201 (11)0.0142 (11)0.0188 (12)0.0018 (9)0.0042 (9)0.0033 (9)
C3A0.0208 (12)0.0197 (12)0.0232 (12)0.0006 (10)0.0024 (10)0.0032 (10)
C4A0.0280 (13)0.0191 (13)0.0190 (12)0.0006 (10)0.0011 (10)0.0002 (10)
C5A0.0296 (14)0.0219 (13)0.0222 (12)0.0005 (10)0.0086 (10)0.0015 (10)
C6A0.0208 (12)0.0251 (13)0.0268 (13)0.0013 (10)0.0088 (10)0.0025 (10)
C7A0.0209 (12)0.0136 (11)0.0212 (12)0.0008 (9)0.0035 (10)0.0040 (9)
N1B0.0205 (10)0.0193 (10)0.0180 (10)0.0013 (8)0.0029 (8)0.0032 (8)
C2B0.0201 (12)0.0194 (12)0.0168 (11)0.0012 (9)0.0034 (9)0.0047 (9)
C3B0.0193 (12)0.0339 (15)0.0263 (13)0.0007 (11)0.0040 (10)0.0016 (11)
C4B0.0206 (13)0.0382 (16)0.0366 (15)0.0041 (11)0.0107 (11)0.0057 (12)
C5B0.0318 (14)0.0277 (14)0.0279 (13)0.0076 (11)0.0134 (11)0.0033 (11)
C6B0.0310 (13)0.0187 (12)0.0199 (12)0.0019 (10)0.0044 (10)0.0021 (10)
C7B0.0195 (12)0.0175 (12)0.0168 (11)0.0027 (9)0.0036 (9)0.0043 (9)
Geometric parameters (Å, º) top
C1—C61.417 (3)C3A—C4A1.353 (3)
C1—C21.422 (3)C3A—H3A0.9500
C1—C71.467 (3)C4A—C5Ai1.425 (3)
C2—O11.355 (3)C4A—H4A0.9500
C2—C31.387 (3)C5A—C6A1.360 (3)
C3—C41.386 (3)C5A—H5A0.9500
C3—H30.9500C6A—C7A1.427 (3)
C4—C51.385 (3)C6A—H6A0.9500
C4—H40.9500N1B—C2B1.351 (3)
C5—C61.389 (3)N1B—C7B1.351 (3)
C5—H50.9500C2B—C3B1.416 (3)
C6—O21.355 (3)C2B—C7Bii1.432 (3)
C7—O31.225 (3)C3B—C4B1.360 (3)
C7—O41.338 (3)C3B—H3B0.9500
O1—H1O0.91 (3)C4B—C5Bii1.419 (3)
O2—H2O0.89 (3)C4B—H4B0.9500
O4—H4O1.09 (3)C5B—C6B1.359 (3)
N1A—C7A1.347 (3)C5B—H5B0.9500
N1A—C2A1.353 (3)C6B—C7B1.422 (3)
C2A—C3A1.423 (3)C6B—H6B0.9500
C2A—C7Ai1.432 (3)
C6—C1—C2117.73 (19)C3A—C4A—C5Ai120.6 (2)
C6—C1—C7123.8 (2)C3A—C4A—H4A119.7
C2—C1—C7118.4 (2)C5Ai—C4A—H4A119.7
O1—C2—C3116.9 (2)C6A—C5A—C4Ai120.6 (2)
O1—C2—C1122.21 (19)C6A—C5A—H5A119.7
C3—C2—C1120.9 (2)C4Ai—C5A—H5A119.7
C4—C3—C2119.4 (2)C5A—C6A—C7A120.6 (2)
C4—C3—H3120.3C5A—C6A—H6A119.7
C2—C3—H3120.3C7A—C6A—H6A119.7
C5—C4—C3121.5 (2)N1A—C7A—C6A119.8 (2)
C5—C4—H4119.2N1A—C7A—C2Ai121.7 (2)
C3—C4—H4119.2C6A—C7A—C2Ai118.5 (2)
C4—C5—C6119.5 (2)C2B—N1B—C7B118.13 (18)
C4—C5—H5120.2N1B—C2B—C3B120.0 (2)
C6—C5—H5120.2N1B—C2B—C7Bii120.81 (19)
O2—C6—C5116.0 (2)C3B—C2B—C7Bii119.2 (2)
O2—C6—C1123.12 (19)C4B—C3B—C2B120.0 (2)
C5—C6—C1120.8 (2)C4B—C3B—H3B120.0
O3—C7—O4121.0 (2)C2B—C3B—H3B120.0
O3—C7—C1123.1 (2)C3B—C4B—C5Bii120.9 (2)
O4—C7—C1116.0 (2)C3B—C4B—H4B119.5
C2—O1—H1O104 (2)C5Bii—C4B—H4B119.5
C6—O2—H2O110.6 (18)C6B—C5B—C4Bii120.9 (2)
C7—O4—H4O110.7 (18)C6B—C5B—H5B119.5
C7A—N1A—C2A116.34 (19)C4Bii—C5B—H5B119.5
N1A—C2A—C3A119.0 (2)C5B—C6B—C7B119.8 (2)
N1A—C2A—C7Ai121.98 (19)C5B—C6B—H6B120.1
C3A—C2A—C7Ai119.0 (2)C7B—C6B—H6B120.1
C4A—C3A—C2A120.7 (2)N1B—C7B—C6B119.78 (19)
C4A—C3A—H3A119.6N1B—C7B—C2Bii121.06 (19)
C2A—C3A—H3A119.6C6B—C7B—C2Bii119.2 (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···AD—HH···AD···AD—H···A
O2—H2O···O40.89 (3)1.86 (3)2.616 (2)141 (3)
O1—H1O···O30.91 (3)1.73 (3)2.568 (2)152 (3)
O4—H4O···N1B1.09 (3)1.60 (3)2.674 (2)168 (3)
C4B—H4B···N1A0.952.743.626 (3)155
C3A—H3A···O3iii0.952.463.070 (3)122
C3A—H3A···O2iv0.952.643.206 (3)119
C5—H5···O1v0.952.533.401 (3)152
C5B—H5B···O2vi0.952.683.300 (3)124
Symmetry codes: (iii) x+1, y+2, z+1; (iv) x+1, y+1, z+1; (v) x, y1, z; (vi) x1/2, y+1/2, z.
 

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