(E)-4,4′-Diaza­stilbene–4,4′-oxydibenzoic acid (1/1)

The title compound, C₁₂H₁₀N₂·C₁₄H₁₀O₅, is a cocrystal of (E)-4,4′-diaza­stilbene and 4,4′-oxydibenzoic acid, lying on an inversion centre and a twofold axis, respectively. Mol­ecules are linked by strong inter­molecular O—H...N hydrogen bonds, resulting in a one-dimensional architecture.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.092
• wR factor = 0.178
• Data-to-parameter ratio = 12.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 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
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2002); software used to prepare material for publication: SHELXL97.

(E)-4,4'-Diazastilbene–4,4'-oxydibenzoic acid (1/1)

Crystal data

C12H10N2·C14H10O5	F(000) = 920
Mr = 440.44	Dx = 1.384 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 662 reflections
a = 13.308 (5) Å	θ = 2.5–22.2°
b = 6.080 (2) Å	µ = 0.10 mm^−1
c = 26.143 (10) Å	T = 298 K
β = 92.603 (7)°	Rod, colourless
V = 2113.1 (13) Å^3	0.21 × 0.10 × 0.09 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	1919 independent reflections
Radiation source: fine-focus sealed tube	1401 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
φ and ω scans	θmax = 25.3°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −14→16
Tmin = 0.975, Tmax = 0.990	k = −6→7
5391 measured reflections	l = −31→31

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)] = 0.092	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.178	H-atom parameters constrained
S = 1.23	w = 1/[σ^2(Fo^2) + (0.0352P)^2 + 1.8866P] where P = (Fo^2 + 2Fc^2)/3
1919 reflections	(Δ/σ)max < 0.001
151 parameters	Δρmax = 0.19 e Å^−3
0 restraints	Δρmin = −0.25 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
O1	0.8443 (2)	0.6954 (5)	0.85291 (10)	0.0660 (8)
H1	0.8936	0.7353	0.8705	0.099*
O2	0.8615 (2)	0.3973 (5)	0.90075 (10)	0.0752 (9)
O3	0.5000	0.1053 (5)	0.7500	0.0566 (10)
N1	0.4931 (2)	0.3587 (5)	0.91063 (11)	0.0514 (8)
C1	0.5306 (3)	0.5534 (7)	0.89850 (12)	0.0510 (9)
H1A	0.5041	0.6239	0.8693	0.061*
C2	0.6062 (2)	0.6555 (6)	0.92681 (12)	0.0477 (9)
H2	0.6298	0.7919	0.9167	0.057*
C3	0.6477 (2)	0.5548 (6)	0.97075 (12)	0.0423 (8)
C4	0.6087 (2)	0.3502 (6)	0.98273 (12)	0.0495 (9)
H4	0.6337	0.2747	1.0115	0.059*
C5	0.5329 (2)	0.2592 (6)	0.95187 (13)	0.0527 (10)
H5	0.5085	0.1213	0.9604	0.063*
C6	0.7263 (2)	0.6572 (5)	1.00387 (13)	0.0483 (9)
H6	0.7447	0.5820	1.0338	0.058*
C7	0.8212 (2)	0.4933 (6)	0.86497 (13)	0.0484 (9)
C8	0.7389 (2)	0.3967 (6)	0.83185 (11)	0.0426 (8)
C9	0.6947 (2)	0.5074 (5)	0.79020 (11)	0.0421 (8)
H9	0.7193	0.6443	0.7810	0.050*
C10	0.6146 (2)	0.4165 (6)	0.76231 (12)	0.0452 (9)
H10	0.5858	0.4907	0.7342	0.054*
C11	0.5777 (2)	0.2149 (5)	0.77638 (11)	0.0408 (8)
C12	0.6231 (3)	0.0997 (6)	0.81624 (13)	0.0506 (9)
H12	0.5994	−0.0388	0.8248	0.061*
C13	0.7034 (3)	0.1896 (6)	0.84346 (13)	0.0520 (10)
H13	0.7345	0.1102	0.8701	0.062*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0698 (19)	0.0620 (19)	0.0639 (17)	−0.0143 (14)	−0.0231 (13)	0.0060 (14)
O2	0.0759 (19)	0.069 (2)	0.0770 (18)	0.0049 (15)	−0.0354 (15)	0.0149 (16)
O3	0.058 (2)	0.041 (2)	0.069 (2)	0.000	−0.0203 (18)	0.000
N1	0.0485 (18)	0.055 (2)	0.0511 (18)	−0.0018 (15)	0.0008 (14)	−0.0106 (16)
C1	0.053 (2)	0.061 (3)	0.0384 (19)	0.0036 (19)	−0.0060 (16)	−0.0008 (19)
C2	0.050 (2)	0.047 (2)	0.0452 (19)	−0.0014 (17)	−0.0021 (17)	−0.0014 (17)
C3	0.0376 (18)	0.050 (2)	0.0389 (18)	0.0044 (16)	−0.0014 (15)	−0.0074 (17)
C4	0.053 (2)	0.051 (2)	0.0444 (19)	0.0042 (18)	−0.0014 (17)	0.0011 (18)
C5	0.049 (2)	0.051 (2)	0.058 (2)	−0.0013 (18)	0.0023 (18)	−0.004 (2)
C6	0.052 (2)	0.053 (2)	0.0393 (17)	0.0042 (17)	−0.0043 (16)	−0.0001 (18)
C7	0.046 (2)	0.048 (2)	0.051 (2)	0.0085 (17)	−0.0024 (17)	−0.0013 (18)
C8	0.0407 (19)	0.046 (2)	0.0414 (18)	0.0100 (16)	0.0027 (15)	−0.0010 (16)
C9	0.045 (2)	0.037 (2)	0.0435 (19)	0.0017 (15)	0.0026 (16)	0.0059 (16)
C10	0.050 (2)	0.044 (2)	0.0414 (18)	0.0041 (17)	−0.0047 (16)	0.0051 (17)
C11	0.043 (2)	0.038 (2)	0.0416 (18)	0.0063 (15)	−0.0002 (15)	−0.0045 (16)
C12	0.058 (2)	0.036 (2)	0.057 (2)	0.0035 (17)	−0.0025 (18)	0.0077 (18)
C13	0.056 (2)	0.049 (2)	0.050 (2)	0.0088 (18)	−0.0099 (18)	0.0068 (18)

Geometric parameters (Å, º)

O1—C7	1.309 (4)	C5—H5	0.9300
O1—H1	0.8200	C6—C6^ii	1.313 (7)
O2—C7	1.208 (4)	C6—H6	0.9300
O3—C11	1.387 (3)	C7—C8	1.485 (4)
O3—C11^i	1.387 (3)	C8—C13	1.383 (5)
N1—C5	1.326 (4)	C8—C9	1.388 (4)
N1—C1	1.328 (4)	C9—C10	1.379 (4)
C1—C2	1.371 (4)	C9—H9	0.9300
C1—H1A	0.9300	C10—C11	1.377 (4)
C2—C3	1.394 (4)	C10—H10	0.9300
C2—H2	0.9300	C11—C12	1.373 (4)
C3—C4	1.389 (5)	C12—C13	1.371 (5)
C3—C6	1.466 (4)	C12—H12	0.9300
C4—C5	1.378 (4)	C13—H13	0.9300
C4—H4	0.9300
C7—O1—H1	109.5	O2—C7—O1	122.7 (3)
C11—O3—C11^i	122.5 (4)	O2—C7—C8	123.4 (4)
C5—N1—C1	117.4 (3)	O1—C7—C8	113.9 (3)
N1—C1—C2	123.3 (3)	C13—C8—C9	118.5 (3)
N1—C1—H1A	118.3	C13—C8—C7	118.8 (3)
C2—C1—H1A	118.3	C9—C8—C7	122.7 (3)
C1—C2—C3	120.0 (4)	C10—C9—C8	120.7 (3)
C1—C2—H2	120.0	C10—C9—H9	119.7
C3—C2—H2	120.0	C8—C9—H9	119.7
C4—C3—C2	116.2 (3)	C11—C10—C9	119.5 (3)
C4—C3—C6	120.7 (3)	C11—C10—H10	120.3
C2—C3—C6	123.1 (3)	C9—C10—H10	120.3
C5—C4—C3	119.9 (3)	C12—C11—C10	120.5 (3)
C5—C4—H4	120.1	C12—C11—O3	115.1 (3)
C3—C4—H4	120.1	C10—C11—O3	124.2 (3)
N1—C5—C4	123.2 (4)	C13—C12—C11	119.8 (3)
N1—C5—H5	118.4	C13—C12—H12	120.1
C4—C5—H5	118.4	C11—C12—H12	120.1
C6^ii—C6—C3	127.5 (4)	C12—C13—C8	121.0 (3)
C6^ii—C6—H6	116.2	C12—C13—H13	119.5
C3—C6—H6	116.2	C8—C13—H13	119.5

Symmetry codes: (i) −x+1, y, −z+3/2; (ii) −x+3/2, −y+3/2, −z+2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1^iii	0.82	1.81	2.629 (4)	172

Symmetry code: (iii) x+1/2, y+1/2, z.