2,5-Di-4-pyridyl-1,3,4-oxadiazole–succinic acid (2/1)

In the title structure, 2C₁₂H₈N₄O·0C₄H₆O₄, succinic acid mol­ecules lie on crystallographic inversion centers and a pair of O—H...N hydrogen bonds links the three molecules. In addition, C—H...O and C—H...N hydrogen bonds link this unit into a two-dimensional framework.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.037
• wR factor = 0.108
• Data-to-parameter ratio = 10.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       2.00 Ratio
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N4     -   C11     ..       5.92 su
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C4 H6 O4

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

   6 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1999); software used to prepare material for publication: SHELXTL.

2,5-Di-4-pyridyl-1,3,4-oxadiazle–succinic acid (2/1)

Crystal data

2C12H8N4O·C4H6O4	Z = 1
Mr = 566.54	F(000) = 294
Triclinic, P1	Dx = 1.444 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.4389 (9) Å	Cell parameters from 400 reflections
b = 9.5462 (13) Å	θ = 7.5–23.0°
c = 11.0415 (15) Å	µ = 0.11 mm^−1
α = 94.803 (2)°	T = 293 K
β = 103.666 (2)°	Block, pale yellow
γ = 96.213 (2)°	0.43 × 0.34 × 0.24 mm
V = 651.39 (15) Å^3

Data collection

Bruker SMART-CCD area-detector diffractometer	2499 independent reflections
Radiation source: fine-focus sealed tube	2227 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.010
φ and ω scans	θmax = 26.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→7
Tmin = 0.956, Tmax = 0.975	k = −11→11
3585 measured reflections	l = −10→13

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.108	All H-atom parameters refined
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0682P)^2 + 0.0637P] where P = (Fo^2 + 2Fc^2)/3
2499 reflections	(Δ/σ)max < 0.001
234 parameters	Δρmax = 0.22 e Å^−3
0 restraints	Δρmin = −0.18 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	0.03374 (13)	0.12665 (8)	0.29475 (8)	0.0409 (2)
O2	−0.10945 (15)	0.85026 (10)	0.05356 (10)	0.0549 (3)
H2B	−0.074 (3)	0.757 (2)	0.0767 (17)	0.086 (6)*
O3	−0.44432 (16)	0.74900 (10)	0.03098 (11)	0.0621 (3)
N1	0.00205 (18)	0.60445 (11)	0.13035 (10)	0.0437 (3)
N2	0.37319 (18)	0.18640 (13)	0.29387 (12)	0.0546 (3)
N3	0.35241 (19)	0.05282 (13)	0.33667 (12)	0.0536 (3)
N4	−0.1419 (2)	−0.34963 (13)	0.44529 (12)	0.0589 (3)
C1	0.2080 (2)	0.58256 (14)	0.16324 (13)	0.0487 (3)
H1A	0.310 (2)	0.6544 (17)	0.1509 (13)	0.054 (4)*
C2	0.2728 (2)	0.46170 (15)	0.21021 (13)	0.0485 (3)
H2A	0.423 (3)	0.4500 (17)	0.2325 (15)	0.061 (4)*
C3	0.1175 (2)	0.35576 (13)	0.22433 (11)	0.0402 (3)
C4	−0.0966 (2)	0.37732 (14)	0.19156 (12)	0.0439 (3)
H4A	−0.209 (2)	0.3105 (17)	0.1992 (13)	0.055 (4)*
C5	−0.1459 (2)	0.50273 (14)	0.14452 (12)	0.0452 (3)
H5A	−0.291 (3)	0.5195 (18)	0.1192 (14)	0.060 (4)*
C6	0.1832 (2)	0.22489 (13)	0.27106 (11)	0.0413 (3)
C7	0.1524 (2)	0.02294 (13)	0.33608 (11)	0.0411 (3)
C8	0.0470 (2)	−0.10319 (12)	0.37423 (11)	0.0405 (3)
C9	0.1722 (2)	−0.19856 (14)	0.43534 (13)	0.0483 (3)
H9A	0.317 (3)	−0.1790 (16)	0.4562 (14)	0.053 (4)*
C10	0.0712 (3)	−0.31857 (15)	0.46747 (14)	0.0568 (4)
H10A	0.157 (3)	−0.387 (2)	0.5099 (16)	0.073 (5)*
C11	−0.2584 (3)	−0.25558 (16)	0.38971 (14)	0.0555 (4)
H11A	−0.416 (3)	−0.2804 (18)	0.3759 (15)	0.065 (5)*
C12	−0.1738 (2)	−0.13186 (14)	0.35270 (12)	0.0468 (3)
H12A	−0.271 (2)	−0.0698 (17)	0.3140 (14)	0.056 (4)*
C13	−0.3189 (2)	0.85253 (13)	0.03145 (11)	0.0418 (3)
C14	−0.3828 (2)	0.99629 (15)	0.00914 (17)	0.0536 (4)
H14A	−0.305 (4)	1.061 (3)	0.082 (2)	0.110 (7)*
H14B	−0.328 (4)	1.032 (3)	−0.059 (2)	0.105 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0386 (5)	0.0356 (4)	0.0494 (5)	0.0092 (3)	0.0092 (4)	0.0086 (4)
O2	0.0403 (5)	0.0434 (5)	0.0854 (7)	0.0095 (4)	0.0173 (5)	0.0235 (5)
O3	0.0453 (6)	0.0417 (5)	0.0995 (8)	0.0030 (4)	0.0146 (5)	0.0223 (5)
N1	0.0478 (6)	0.0386 (6)	0.0469 (6)	0.0088 (4)	0.0129 (5)	0.0096 (4)
N2	0.0446 (7)	0.0525 (7)	0.0721 (8)	0.0125 (5)	0.0157 (5)	0.0258 (6)
N3	0.0444 (6)	0.0507 (6)	0.0704 (7)	0.0148 (5)	0.0137 (5)	0.0243 (5)
N4	0.0700 (9)	0.0446 (6)	0.0658 (8)	0.0054 (6)	0.0234 (6)	0.0103 (5)
C1	0.0457 (7)	0.0436 (7)	0.0583 (8)	0.0014 (6)	0.0153 (6)	0.0141 (6)
C2	0.0382 (7)	0.0497 (8)	0.0603 (8)	0.0076 (6)	0.0134 (6)	0.0152 (6)
C3	0.0424 (7)	0.0383 (6)	0.0414 (6)	0.0076 (5)	0.0114 (5)	0.0068 (5)
C4	0.0394 (7)	0.0382 (6)	0.0546 (7)	0.0038 (5)	0.0116 (5)	0.0101 (5)
C5	0.0412 (7)	0.0423 (7)	0.0540 (7)	0.0104 (5)	0.0117 (6)	0.0097 (5)
C6	0.0397 (6)	0.0400 (6)	0.0449 (6)	0.0059 (5)	0.0101 (5)	0.0093 (5)
C7	0.0434 (7)	0.0381 (6)	0.0424 (6)	0.0126 (5)	0.0070 (5)	0.0079 (5)
C8	0.0469 (7)	0.0359 (6)	0.0392 (6)	0.0108 (5)	0.0094 (5)	0.0034 (5)
C9	0.0480 (8)	0.0455 (7)	0.0536 (7)	0.0144 (6)	0.0113 (6)	0.0116 (6)
C10	0.0711 (10)	0.0446 (8)	0.0601 (8)	0.0189 (7)	0.0182 (7)	0.0170 (6)
C11	0.0529 (9)	0.0505 (8)	0.0620 (8)	−0.0003 (6)	0.0176 (7)	0.0003 (6)
C12	0.0462 (7)	0.0439 (7)	0.0497 (7)	0.0107 (6)	0.0089 (6)	0.0045 (5)
C13	0.0414 (7)	0.0378 (6)	0.0475 (7)	0.0052 (5)	0.0114 (5)	0.0106 (5)
C14	0.0438 (8)	0.0389 (7)	0.0796 (10)	0.0078 (6)	0.0137 (7)	0.0169 (7)

Geometric parameters (Å, º)

O1—C6	1.3560 (15)	C3—C6	1.4578 (17)
O1—C7	1.3590 (14)	C4—C5	1.3828 (18)
O2—C13	1.3153 (15)	C4—H4A	0.937 (15)
O2—H2B	0.99 (2)	C5—H5A	0.947 (16)
O3—C13	1.2057 (15)	C7—C8	1.4599 (18)
N1—C5	1.3306 (17)	C8—C12	1.3776 (19)
N1—C1	1.3339 (18)	C8—C9	1.3925 (18)
N2—C6	1.2892 (17)	C9—C10	1.370 (2)
N2—N3	1.4004 (16)	C9—H9A	0.899 (15)
N3—C7	1.2868 (17)	C10—H10A	0.980 (19)
N4—C11	1.329 (2)	C11—C12	1.380 (2)
N4—C10	1.331 (2)	C11—H11A	0.991 (17)
C1—C2	1.3697 (19)	C12—H12A	0.958 (17)
C1—H1A	0.937 (16)	C13—C14	1.4981 (18)
C2—C3	1.3886 (18)	C14—C14^i	1.485 (3)
C2—H2A	0.960 (16)	C14—H14A	0.97 (2)
C3—C4	1.3827 (19)	C14—H14B	0.97 (2)
C6—O1—C7	102.56 (9)	O1—C7—C8	119.28 (11)
C13—O2—H2B	109.9 (11)	C12—C8—C9	118.14 (13)
C5—N1—C1	117.55 (11)	C12—C8—C7	122.42 (12)
C6—N2—N3	106.09 (11)	C9—C8—C7	119.44 (12)
C7—N3—N2	106.28 (10)	C10—C9—C8	118.90 (14)
C11—N4—C10	116.29 (13)	C10—C9—H9A	121.0 (10)
N1—C1—C2	123.31 (12)	C8—C9—H9A	120.0 (10)
N1—C1—H1A	116.4 (10)	N4—C10—C9	123.89 (13)
C2—C1—H1A	120.3 (10)	N4—C10—H10A	116.4 (10)
C1—C2—C3	118.85 (13)	C9—C10—H10A	119.7 (10)
C1—C2—H2A	120.7 (10)	N4—C11—C12	124.69 (14)
C3—C2—H2A	120.5 (9)	N4—C11—H11A	114.6 (10)
C4—C3—C2	118.53 (12)	C12—C11—H11A	120.7 (10)
C4—C3—C6	121.92 (12)	C8—C12—C11	118.07 (13)
C2—C3—C6	119.54 (12)	C8—C12—H12A	123.2 (9)
C3—C4—C5	118.30 (12)	C11—C12—H12A	118.8 (9)
C3—C4—H4A	123.0 (10)	O3—C13—O2	122.76 (12)
C5—C4—H4A	118.7 (10)	O3—C13—C14	124.15 (12)
N1—C5—C4	123.46 (12)	O2—C13—C14	113.08 (11)
N1—C5—H5A	116.3 (10)	C14^i—C14—C13	114.22 (14)
C4—C5—H5A	120.2 (10)	C14^i—C14—H14A	108.8 (13)
N2—C6—O1	112.58 (11)	C13—C14—H14A	106.9 (14)
N2—C6—C3	128.00 (12)	C14^i—C14—H14B	112.1 (14)
O1—C6—C3	119.42 (11)	C13—C14—H14B	110.3 (14)
N3—C7—O1	112.48 (11)	H14A—C14—H14B	103.9 (17)
N3—C7—C8	128.24 (11)
C6—N2—N3—C7	−0.13 (15)	N2—N3—C7—C8	−178.91 (12)
C5—N1—C1—C2	0.0 (2)	C6—O1—C7—N3	−0.62 (14)
N1—C1—C2—C3	0.2 (2)	C6—O1—C7—C8	178.83 (10)
C1—C2—C3—C4	−0.7 (2)	N3—C7—C8—C12	−170.66 (13)
C1—C2—C3—C6	178.38 (12)	O1—C7—C8—C12	9.98 (18)
C2—C3—C4—C5	0.9 (2)	N3—C7—C8—C9	9.7 (2)
C6—C3—C4—C5	−178.12 (11)	O1—C7—C8—C9	−169.66 (11)
C1—N1—C5—C4	0.2 (2)	C12—C8—C9—C10	2.2 (2)
C3—C4—C5—N1	−0.7 (2)	C7—C8—C9—C10	−178.15 (12)
N3—N2—C6—O1	−0.27 (15)	C11—N4—C10—C9	−0.7 (2)
N3—N2—C6—C3	−179.90 (13)	C8—C9—C10—N4	−0.9 (2)
C7—O1—C6—N2	0.54 (14)	C10—N4—C11—C12	1.1 (2)
C7—O1—C6—C3	−179.80 (11)	C9—C8—C12—C11	−1.84 (19)
C4—C3—C6—N2	173.14 (13)	C7—C8—C12—C11	178.51 (12)
C2—C3—C6—N2	−5.9 (2)	N4—C11—C12—C8	0.2 (2)
C4—C3—C6—O1	−6.47 (19)	O3—C13—C14—C14^i	2.3 (3)
C2—C3—C6—O1	174.50 (11)	O2—C13—C14—C14^i	−176.81 (17)
N2—N3—C7—O1	0.48 (15)

Symmetry code: (i) −x−1, −y+2, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2B···N1	0.982 (19)	1.695 (19)	2.6741 (15)	174.3 (16)
C1—H1A···O3^ii	0.938 (15)	2.440 (14)	3.2912 (18)	150.9 (12)
C10—H10A···N4^iii	0.979 (19)	2.599 (19)	3.433 (2)	143.1 (15)

Symmetry codes: (ii) x+1, y, z; (iii) −x, −y−1, −z+1.