2,5-Di-4-pyridinio-1,3,4-oxadiazole bis­(perchlorate) monohydrate

In the title structure, C₁₂H₁₀N₄O²⁺·2ClO₄⁻·H₂O, the dication is not planar and N—H...O hydrogen bonds link it to perchlorate anions and water mol­ecules. In addition, N—H...O and O—H...O hydrogen bonds link these units into a three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.005 Å
• Disorder in solvent or counterion
• R factor = 0.059
• wR factor = 0.165
• Data-to-parameter ratio = 11.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT430_ALERT_2_B Short Inter D...A Contact  O5     ..  O6'     ..       2.64 Ang.
PLAT432_ALERT_2_B Short Inter X...Y Contact  O3     ..  C8      ..       2.85 Ang.

Alert level C
ABSTM02_ALERT_3_C  The ratio of Tmax/Tmin expected RT(exp) is > 1.10
            Absorption corrections should be applied.
            Tmin and Tmax expected:      0.835     0.983
            RT(exp) =      1.177
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT057_ALERT_3_C Correction for Absorption Required   RT(exp) ...       1.18
PLAT243_ALERT_4_C High  'Solvent' Ueq as Compared to Neighbors for        O5'
PLAT243_ALERT_4_C High  'Solvent' Ueq as Compared to Neighbors for        O6'
PLAT243_ALERT_4_C High  'Solvent' Ueq as Compared to Neighbors for         O7
PLAT243_ALERT_4_C High  'Solvent' Ueq as Compared to Neighbors for        O7'
PLAT243_ALERT_4_C High  'Solvent' Ueq as Compared to Neighbors for        O8'
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        Cl1
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        Cl2
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      42.00 Perc.
PLAT313_ALERT_2_C Oxygen with three covalent bonds (rare) ........        O5'
PLAT313_ALERT_2_C Oxygen with three covalent bonds (rare) ........         O6
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT430_ALERT_2_C Short Inter D...A Contact  O6     ..  O9      ..       2.86 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  O6     ..  C6      ..       2.97 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2
PLAT731_ALERT_1_C Bond    Calc     0.84(3), Rep   0.840(10) ......       3.00 su-Rat
              N1   -H1N     1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.85(4), Rep   0.850(10) ......       4.00 su-Rat
              N4   -H4N     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.84(3), Rep   0.840(10) ......       3.00 su-Rat
              N1   -H1N     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.84(3), Rep   0.840(10) ......       3.00 su-Rat
              N1   -H1N     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.84(3), Rep   0.840(10) ......       3.00 su-Rat
              N1   -H1N     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.84(3), Rep   0.840(10) ......       3.00 su-Rat
              N1   -H1N     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.85(4), Rep   0.850(10) ......       4.00 su-Rat
              N4   -H4N     1.555   1.555

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

   8 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   9 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

2,5-Di-4-pyridinio-1,3,4-oxadiazole bis(perchlorate) monohydrate

Crystal data

C12H10N4O^2+·2ClO4^−·H2O	F(000) = 904
Mr = 443.16	Dx = 1.698 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2189 reflections
a = 5.4662 (5) Å	θ = 2.4–23.7°
b = 19.448 (2) Å	µ = 0.44 mm^−1
c = 16.383 (1) Å	T = 295 K
β = 95.609 (1)°	Plate, colourless
V = 1733.2 (3) Å^3	0.47 × 0.35 × 0.04 mm
Z = 4

Data collection

Bruker APEX area-detector diffractometer	2879 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.032
Graphite monochromator	θmax = 27.5°, θmin = 1.6°
φ and ω scans	h = −7→7
10264 measured reflections	k = −19→25
3882 independent reflections	l = −21→21

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) = 0.165	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0819P)^2 + 0.8074P] where P = (Fo^2 + 2Fc^2)/3
3882 reflections	(Δ/σ)max = 0.001
332 parameters	Δρmax = 0.30 e Å^−3
483 restraints	Δρmin = −0.29 e Å^−3

Special details

Experimental. Analysis, found: C 32.1, H 2.72, N 12.57%; calculated: C 32.52, H 2.73, N 12.64%. IR (KBr, ν, cm^-1): 3450, 2440, 1700, 1608, 1572, 1533, 1413, 1277, 1212, 1101, 1013, 838, 740, 720.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl1	0.1239 (2)	1.04338 (5)	0.62411 (5)	0.0480 (3)
Cl2	0.6113 (2)	0.20534 (6)	0.23278 (7)	0.0636 (4)
O1	0.280 (2)	1.0007 (5)	0.5842 (7)	0.115 (4)	0.73 (2)
O2	−0.107 (1)	1.0129 (4)	0.6320 (6)	0.077 (2)	0.73 (2)
O3	0.236 (1)	1.0610 (6)	0.7037 (3)	0.082 (3)	0.73 (2)
O4	0.086 (1)	1.1062 (3)	0.5798 (5)	0.071 (2)	0.73 (2)
O5	0.347 (1)	0.2072 (4)	0.2067 (6)	0.093 (3)	0.50
O6	0.730 (2)	0.2315 (5)	0.1679 (5)	0.115 (3)	0.50
O7	0.676 (2)	0.1377 (4)	0.2506 (7)	0.104 (4)	0.50
O8	0.649 (2)	0.2480 (6)	0.3025 (5)	0.085 (4)	0.50
O1'	0.249 (4)	1.0072 (9)	0.565 (1)	0.064 (5)	0.27 (2)
O2'	−0.131 (2)	1.025 (1)	0.612 (1)	0.066 (6)	0.27 (2)
O3'	0.152 (4)	1.1135 (4)	0.617 (2)	0.085 (6)	0.27 (2)
O4'	0.219 (3)	1.018 (2)	0.7009 (9)	0.095 (7)	0.27 (2)
O5'	0.460 (2)	0.2116 (5)	0.1616 (5)	0.114 (3)	0.50
O6'	0.866 (1)	0.2026 (5)	0.2118 (6)	0.124 (4)	0.50
O7'	0.580 (2)	0.1419 (4)	0.2730 (6)	0.107 (4)	0.50
O8'	0.598 (2)	0.2602 (5)	0.2877 (6)	0.096 (4)	0.50
O9	0.5582 (4)	0.6539 (1)	0.4556 (1)	0.0420 (6)
O1W	0.1160 (8)	0.3337 (2)	0.2224 (3)	0.112 (2)
N1	0.6157 (7)	0.8916 (2)	0.5679 (2)	0.0554 (9)
N2	0.9237 (6)	0.6524 (2)	0.5256 (2)	0.0536 (8)
N3	0.8819 (7)	0.5889 (2)	0.4868 (2)	0.0548 (9)
N4	0.3053 (7)	0.4384 (2)	0.3070 (2)	0.0555 (9)
C1	0.8118 (8)	0.8590 (2)	0.6032 (2)	0.053 (1)
C2	0.8504 (7)	0.7921 (2)	0.5835 (2)	0.0475 (9)
C3	0.6837 (7)	0.7597 (2)	0.5270 (2)	0.0404 (8)
C4	0.4787 (7)	0.7951 (2)	0.4923 (2)	0.0478 (9)
C5	0.4506 (8)	0.8624 (2)	0.5145 (2)	0.054 (1)
C6	0.7304 (7)	0.6884 (2)	0.5045 (2)	0.0416 (8)
C7	0.6690 (7)	0.5925 (2)	0.4474 (2)	0.0413 (8)
C8	0.5109 (9)	0.4232 (2)	0.3520 (2)	0.053 (1)
C9	0.6337 (8)	0.4730 (2)	0.3990 (2)	0.0479 (9)
C10	0.5386 (7)	0.5390 (2)	0.3974 (2)	0.0425 (8)
C11	0.3236 (7)	0.5533 (2)	0.3487 (2)	0.0512 (9)
C12	0.2090 (8)	0.5013 (2)	0.3032 (3)	0.057 (1)
H1W1	−0.0364	0.3344	0.2030	0.135*
H1W2	0.1922	0.3102	0.1856	0.135*
H1N	0.586 (9)	0.932 (1)	0.582 (3)	0.067*
H4N	0.237 (8)	0.407 (2)	0.277 (2)	0.067*
H1	0.9216	0.8817	0.6410	0.064*
H2	0.9868	0.7685	0.6077	0.057*
H4	0.3638	0.7738	0.4550	0.057*
H5	0.3155	0.8875	0.4921	0.065*
H8	0.5729	0.3787	0.3519	0.064*
H9	0.7783	0.4627	0.4315	0.057*
H11	0.2578	0.5974	0.3469	0.061*
H12	0.0648	0.5100	0.2698	0.068*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0491 (6)	0.0481 (5)	0.0465 (5)	0.0070 (4)	0.0027 (4)	−0.0022 (4)
Cl2	0.0705 (8)	0.0612 (7)	0.0584 (7)	−0.0178 (5)	0.0029 (5)	−0.0056 (5)
O1	0.121 (6)	0.104 (6)	0.122 (7)	0.070 (5)	0.021 (5)	−0.019 (5)
O2	0.086 (5)	0.064 (4)	0.082 (4)	−0.030 (3)	0.014 (3)	−0.007 (3)
O3	0.069 (3)	0.119 (6)	0.056 (3)	−0.005 (3)	−0.007 (2)	−0.010 (3)
O4	0.077 (4)	0.059 (3)	0.077 (4)	0.003 (2)	0.007 (3)	0.017 (3)
O5	0.067 (5)	0.069 (5)	0.137 (7)	−0.003 (4)	−0.022 (5)	−0.030 (5)
O6	0.153 (8)	0.124 (7)	0.072 (5)	−0.036 (6)	0.040 (5)	−0.007 (5)
O7	0.088 (7)	0.080 (6)	0.140 (8)	0.026 (5)	−0.009 (6)	0.011 (5)
O8	0.079 (6)	0.103 (7)	0.067 (5)	0.017 (5)	−0.019 (4)	−0.019 (5)
O1'	0.077 (9)	0.059 (8)	0.057 (7)	0.016 (7)	0.013 (6)	−0.002 (6)
O2'	0.044 (7)	0.059 (8)	0.09 (1)	0.012 (6)	−0.019 (6)	0.016 (7)
O3'	0.08 (1)	0.051 (7)	0.12 (1)	−0.003 (6)	0.008 (9)	−0.028 (7)
O4'	0.083 (9)	0.13 (1)	0.068 (8)	0.028 (9)	−0.004 (6)	0.019 (8)
O5'	0.152 (9)	0.101 (6)	0.078 (5)	−0.013 (6)	−0.042 (5)	0.007 (5)
O6'	0.118 (7)	0.136 (8)	0.125 (7)	−0.015 (6)	0.047 (6)	−0.027 (6)
O7'	0.127 (9)	0.088 (6)	0.106 (6)	−0.005 (5)	0.019 (6)	0.024 (5)
O8'	0.104 (8)	0.090 (6)	0.088 (7)	0.027 (5)	−0.020 (5)	−0.027 (5)
O9	0.043 (1)	0.036 (1)	0.046 (1)	0.006 (1)	−0.002 (1)	0.000 (1)
O1W	0.097 (3)	0.074 (2)	0.161 (4)	−0.014 (2)	−0.018 (3)	−0.039 (2)
N1	0.074 (2)	0.036 (2)	0.057 (2)	0.011 (2)	0.004 (2)	−0.003 (2)
N2	0.055 (2)	0.042 (2)	0.061 (2)	0.009 (2)	−0.012 (2)	−0.008 (2)
N3	0.058 (2)	0.042 (2)	0.061 (2)	0.011 (2)	−0.011 (2)	−0.008 (1)
N4	0.062 (2)	0.053 (2)	0.052 (2)	−0.017 (2)	0.008 (2)	−0.010 (2)
C1	0.062 (3)	0.045 (2)	0.050 (2)	0.001 (2)	−0.002 (2)	−0.005 (2)
C2	0.053 (2)	0.039 (2)	0.049 (2)	0.006 (2)	−0.002 (2)	−0.001 (2)
C3	0.044 (2)	0.036 (2)	0.042 (2)	0.004 (1)	0.006 (2)	0.003 (1)
C4	0.048 (2)	0.044 (2)	0.051 (2)	0.003 (2)	0.001 (2)	0.003 (2)
C5	0.056 (3)	0.048 (2)	0.058 (2)	0.016 (2)	0.004 (2)	0.006 (2)
C6	0.047 (2)	0.037 (2)	0.041 (2)	0.003 (2)	0.001 (2)	0.002 (1)
C7	0.047 (2)	0.035 (2)	0.041 (2)	0.006 (2)	0.001 (2)	0.001 (1)
C8	0.072 (3)	0.040 (2)	0.050 (2)	0.000 (2)	0.010 (2)	−0.003 (2)
C9	0.056 (2)	0.041 (2)	0.046 (2)	0.005 (2)	0.001 (2)	0.000 (2)
C10	0.048 (2)	0.038 (2)	0.042 (2)	0.001 (2)	0.004 (2)	0.002 (1)
C11	0.049 (2)	0.049 (2)	0.054 (2)	0.004 (2)	−0.002 (2)	−0.001 (2)
C12	0.050 (2)	0.063 (3)	0.056 (2)	−0.005 (2)	−0.003 (2)	−0.003 (2)

Geometric parameters (Å, º)

Cl1—O3'	1.378 (7)	N4—C12	1.330 (5)
Cl1—O1	1.396 (5)	C1—C2	1.363 (5)
Cl1—O4'	1.405 (7)	C2—C3	1.386 (5)
Cl1—O2	1.410 (5)	C3—C4	1.389 (5)
Cl1—O1'	1.420 (8)	C3—C6	1.463 (5)
Cl1—O4	1.425 (4)	C4—C5	1.371 (5)
Cl1—O3	1.427 (4)	C7—C10	1.465 (5)
Cl1—O2'	1.431 (7)	C8—C9	1.372 (5)
Cl2—O5'	1.366 (6)	C9—C10	1.384 (5)
Cl2—O7	1.385 (6)	C10—C11	1.382 (5)
Cl2—O6	1.396 (5)	C11—C12	1.371 (5)
Cl2—O8'	1.402 (6)	O1W—H1W1	0.86
Cl2—O8	1.410 (6)	O1W—H1W2	0.89
Cl2—O7'	1.416 (6)	N1—H1N	0.84 (1)
Cl2—O5	1.466 (5)	N4—H4N	0.85 (1)
Cl2—O6'	1.468 (6)	C1—H1	0.9300
O9—C7	1.352 (4)	C2—H2	0.9300
O9—C6	1.353 (4)	C4—H4	0.9300
N1—C5	1.323 (5)	C5—H5	0.9300
N1—C1	1.328 (5)	C8—H8	0.9300
N2—C6	1.286 (5)	C9—H9	0.9300
N2—N3	1.397 (4)	C11—H11	0.9300
N3—C7	1.276 (5)	C12—H12	0.9300
N4—C8	1.316 (6)
O3'—Cl1—O4'	113.3 (7)	N1—C5—C4	119.9 (4)
O1—Cl1—O2	112.6 (4)	N2—C6—O9	113.3 (3)
O3'—Cl1—O1'	111.3 (7)	N2—C6—C3	127.4 (3)
O4'—Cl1—O1'	106 (1)	O9—C6—C3	119.4 (3)
O1—Cl1—O4	109.6 (4)	N3—C7—O9	113.1 (3)
O2—Cl1—O4	108.6 (4)	N3—C7—C10	127.9 (3)
O1—Cl1—O3	110.2 (5)	O9—C7—C10	119.0 (3)
O2—Cl1—O3	109.0 (4)	N4—C8—C9	120.0 (4)
O4—Cl1—O3	106.7 (3)	C8—C9—C10	118.8 (4)
O3'—Cl1—O2'	110.1 (7)	C11—C10—C9	119.6 (4)
O4'—Cl1—O2'	108.1 (7)	C11—C10—C7	121.3 (3)
O1'—Cl1—O2'	107.8 (7)	C9—C10—C7	119.1 (3)
O7—Cl2—O6	112.3 (5)	C12—C11—C10	118.9 (4)
O5'—Cl2—O8'	114.6 (6)	C12—C11—H11	120.6
O7—Cl2—O8	112.0 (5)	C10—C11—H11	120.6
O6—Cl2—O8	111.1 (5)	N4—C12—C11	119.7 (4)
O5'—Cl2—O7'	112.6 (5)	H1W1—O1W—H1W2	104.9
O8'—Cl2—O7'	110.4 (5)	C5—N1—H1N	116 (3)
O7—Cl2—O5	107.9 (5)	C1—N1—H1N	120 (3)
O6—Cl2—O5	106.7 (5)	C8—N4—H4N	118 (3)
O8—Cl2—O5	106.4 (5)	C12—N4—H4N	119 (3)
O5'—Cl2—O6'	108.1 (5)	N1—C1—H1	120.3
O8'—Cl2—O6'	106.6 (5)	C2—C1—H1	120.3
O7'—Cl2—O6'	103.8 (5)	C1—C2—H2	120.5
C7—O9—C6	101.8 (3)	C3—C2—H2	120.5
C5—N1—C1	123.5 (3)	C5—C4—H4	120.9
C6—N2—N3	105.4 (3)	C3—C4—H4	120.9
C7—N3—N2	106.4 (3)	N1—C5—H5	120.0
C8—N4—C12	123.0 (4)	C4—C5—H5	120.0
N1—C1—C2	119.4 (4)	N4—C8—H8	120.0
C1—C2—C3	119.0 (4)	C9—C8—H8	120.0
C2—C3—C4	120.0 (3)	C8—C9—H9	120.6
C2—C3—C6	118.7 (3)	C10—C9—H9	120.6
C4—C3—C6	121.3 (3)	N4—C12—H12	120.2
C5—C4—C3	118.1 (4)	C11—C12—H12	120.2
C6—N2—N3—C7	−0.7 (4)	N2—N3—C7—O9	0.0 (4)
C5—N1—C1—C2	0.9 (6)	N2—N3—C7—C10	−179.3 (3)
N1—C1—C2—C3	0.0 (6)	C6—O9—C7—N3	0.6 (4)
C1—C2—C3—C4	−1.0 (6)	C6—O9—C7—C10	−180.0 (3)
C1—C2—C3—C6	178.3 (3)	C12—N4—C8—C9	1.3 (6)
C2—C3—C4—C5	1.1 (5)	N4—C8—C9—C10	−0.7 (6)
C6—C3—C4—C5	−178.1 (3)	C8—C9—C10—C11	−0.1 (6)
C1—N1—C5—C4	−0.8 (6)	C8—C9—C10—C7	−179.9 (3)
C3—C4—C5—N1	−0.3 (6)	N3—C7—C10—C11	−170.6 (4)
N3—N2—C6—O9	1.1 (4)	O9—C7—C10—C11	10.1 (5)
N3—N2—C6—C3	−178.4 (3)	N3—C7—C10—C9	9.3 (6)
C7—O9—C6—N2	−1.1 (4)	O9—C7—C10—C9	−170.1 (3)
C7—O9—C6—C3	178.5 (3)	C9—C10—C11—C12	0.2 (6)
C2—C3—C6—N2	−6.8 (6)	C7—C10—C11—C12	−180.0 (4)
C4—C3—C6—N2	172.4 (4)	C8—N4—C12—C11	−1.2 (6)
C2—C3—C6—O9	173.7 (3)	C10—C11—C12—N4	0.4 (6)
C4—C3—C6—O9	−7.1 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1	0.84 (1)	2.14 (3)	2.84 (1)	140 (4)
N1—H1N···O1′	0.84 (1)	2.34 (4)	3.01 (2)	136 (4)
N1—H1N···O2^i	0.84 (1)	2.39 (4)	2.94 (1)	124 (4)
N1—H1N···O2′^i	0.84 (1)	2.40 (4)	3.00 (2)	128 (4)
N4—H4N···O1W	0.85 (1)	1.77 (2)	2.62 (1)	172 (5)
O1W—H1W1···O3^ii	0.86	2.39	2.91 (1)	120
O1W—H1W1···O3′^ii	0.86	2.34	3.11 (2)	148
O1W—H1W2···O5	0.89	2.19	2.79 (1)	124

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