2,2'-(Ethane-1,2-di­yl)dibenzimidazolium bis­(perchlorate) tetra­hydrate

The cation, anion and water mol­ecules of the title compound, C₁₆H₁₆N₄²⁺·2ClO₄^-·4H₂O, are linked by hydrogen bonds into a three-dimensional network. The cation lies on a center of inversion, which is located at the mid-point of the -CH₂CH₂- bond.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.069
• wR factor = 0.218
• Data-to-parameter ratio = 14.6

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT731_ALERT_1_B Bond    Calc     0.84(5), Rep   0.850(10) ......       5.00 su-Ra
              O2W  -H2W2    1.555   1.555
PLAT735_ALERT_1_B D-H     Calc     0.84(5), Rep   0.850(10) ......       5.00 su-Ra
              O2W  -H4#     1.555   1.555

Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.06
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        Cl1
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          4
PLAT731_ALERT_1_C Bond    Calc     0.84(3), Rep   0.840(10) ......       3.00 su-Ra
              O1W  -H1W1    1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.85(4), Rep   0.850(10) ......       4.00 su-Ra
              O2W  -H2W1    1.555   1.555
PLAT732_ALERT_1_C Angle   Calc      110(5), Rep      109(2) ......       2.50 su-Ra
              H2W1 -O2W  -H2W2    1.555   1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.84(3), Rep   0.840(10) ......       3.00 su-Ra
              O1W  -H1#     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.85(4), Rep   0.850(10) ......       4.00 su-Ra
              O2W  -H3#     1.555   1.555

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

   7 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXL97.

(I)

Crystal data

C16H16N4^2+·2ClO4^−·4H2O	F(000) = 556
Mr = 535.29	Dx = 1.553 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2188 reflections
a = 7.0898 (6) Å	θ = 3.1–25.0°
b = 17.204 (2) Å	µ = 0.35 mm^−1
c = 9.9894 (9) Å	T = 295 K
β = 110.072 (2)°	Block, pale yellow
V = 1144.4 (2) Å^3	0.20 × 0.16 × 0.11 mm
Z = 2

Data collection

Bruker APEX-II area-detector diffractometer	1988 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.034
Graphite monochromator	θmax = 27.5°, θmin = 2.4°
φ and ω scans	h = −8→9
7440 measured reflections	k = −22→19
2601 independent reflections	l = −12→12

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)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.218	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.1223P)^2 + 0.991P] where P = (Fo^2 + 2Fc^2)/3
2601 reflections	(Δ/σ)max = 0.001
178 parameters	Δρmax = 0.99 e Å^−3
32 restraints	Δρmin = −0.48 e Å^−3

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

	x	y	z	Uiso*/Ueq
Cl1	0.4726 (1)	0.81213 (6)	0.03098 (8)	0.0487 (3)
O1	0.6155 (4)	0.7934 (2)	0.1676 (3)	0.073 (1)
O2	0.3585 (7)	0.8759 (3)	0.0352 (6)	0.124 (2)
O3	0.3360 (7)	0.7479 (3)	−0.0099 (6)	0.132 (2)
O4	0.5715 (7)	0.8161 (4)	−0.0658 (5)	0.146 (2)
O1w	0.3827 (4)	0.7180 (2)	0.3212 (3)	0.050 (1)
O2w	0.4845 (4)	0.2943 (2)	0.3515 (3)	0.052 (1)
N1	0.3205 (4)	0.5663 (2)	0.1986 (3)	0.039 (1)
N2	0.3613 (5)	0.4426 (2)	0.2389 (3)	0.040 (1)
C1	0.4254 (6)	0.5281 (2)	0.4546 (3)	0.048 (1)
C2	0.3729 (5)	0.5123 (2)	0.2995 (3)	0.038 (1)
C3	0.2715 (5)	0.5307 (2)	0.0652 (3)	0.037 (1)
C4	0.2080 (6)	0.5596 (2)	−0.0730 (4)	0.050 (1)
C5	0.1718 (6)	0.5058 (3)	−0.1808 (4)	0.057 (1)
C6	0.1992 (6)	0.4259 (3)	−0.1540 (4)	0.058 (1)
C7	0.2625 (6)	0.3970 (2)	−0.0166 (4)	0.048 (1)
C8	0.2976 (5)	0.4518 (2)	0.0918 (3)	0.038 (1)
H1w1	0.480 (4)	0.737 (2)	0.302 (4)	0.07 (2)*
H1w2	0.396 (6)	0.725 (3)	0.408 (2)	0.07 (1)*
H2w1	0.583 (5)	0.289 (3)	0.323 (5)	0.08 (2)*
H2w2	0.402 (7)	0.258 (3)	0.319 (8)	0.15 (3)*
H1n	0.328 (6)	0.614 (1)	0.224 (4)	0.05 (1)*
H2n	0.394 (5)	0.399 (1)	0.279 (3)	0.04 (1)*
H1a	0.4795	0.5803	0.4749	0.058*
H1b	0.3043	0.5258	0.4789	0.058*
H4	0.1909	0.6126	−0.0916	0.060*
H5	0.1277	0.5231	−0.2747	0.068*
H6	0.1742	0.3916	−0.2301	0.070*
H7	0.2805	0.3441	0.0023	0.057*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0438 (5)	0.0667 (6)	0.0347 (5)	0.0097 (4)	0.0121 (4)	−0.0030 (3)
O1	0.055 (2)	0.119 (3)	0.041 (2)	−0.0098 (17)	0.0100 (13)	0.0131 (15)
O2	0.106 (3)	0.101 (3)	0.156 (4)	0.040 (3)	0.033 (3)	−0.029 (3)
O3	0.093 (3)	0.112 (3)	0.141 (4)	−0.009 (2)	−0.023 (3)	−0.048 (3)
O4	0.097 (3)	0.284 (7)	0.072 (2)	0.079 (4)	0.049 (2)	0.079 (3)
O1w	0.056 (2)	0.047 (1)	0.048 (2)	−0.001 (1)	0.020 (1)	0.004 (1)
O2w	0.048 (2)	0.046 (1)	0.061 (2)	−0.001 (1)	0.018 (1)	0.000 (1)
N1	0.047 (2)	0.029 (1)	0.035 (1)	−0.001 (1)	0.007 (1)	−0.002 (1)
N2	0.056 (2)	0.031 (1)	0.031 (1)	−0.001 (1)	0.010 (1)	0.001 (1)
C1	0.060 (2)	0.045 (2)	0.033 (2)	0.007 (2)	0.008 (2)	−0.004 (1)
C2	0.043 (2)	0.037 (2)	0.032 (2)	0.001 (1)	0.008 (1)	−0.003 (1)
C3	0.035 (2)	0.040 (2)	0.031 (2)	−0.002 (1)	0.007 (1)	0.000 (1)
C4	0.049 (2)	0.057 (2)	0.039 (2)	0.002 (2)	0.009 (2)	0.010 (2)
C5	0.049 (2)	0.088 (3)	0.028 (2)	−0.002 (2)	0.006 (1)	0.003 (2)
C6	0.058 (2)	0.076 (3)	0.036 (2)	−0.009 (2)	0.011 (2)	−0.017 (2)
C7	0.054 (2)	0.044 (2)	0.040 (2)	−0.002 (2)	0.010 (2)	−0.012 (1)
C8	0.040 (2)	0.041 (2)	0.029 (1)	0.000 (1)	0.007 (1)	−0.003 (1)

Geometric parameters (Å, º)

Cl1—O2	1.372 (4)	C6—C7	1.381 (5)
Cl1—O4	1.377 (4)	C7—C8	1.392 (4)
Cl1—O1	1.430 (3)	O1w—H1w1	0.84 (1)
Cl1—O3	1.433 (5)	O1w—H1w2	0.84 (1)
N1—C2	1.327 (4)	O2w—H2w1	0.85 (1)
N1—C3	1.398 (4)	O2w—H2w2	0.85 (1)
N2—C2	1.332 (4)	N1—H1n	0.85 (1)
N2—C8	1.390 (4)	N2—H2n	0.85 (1)
C1—C1^i	1.489 (7)	C1—H1a	0.97
C1—C2	1.489 (4)	C1—H1b	0.97
C3—C8	1.384 (4)	C4—H4	0.93
C3—C4	1.389 (4)	C5—H5	0.93
C4—C5	1.375 (5)	C6—H6	0.93
C5—C6	1.402 (6)	C7—H7	0.93
O2—Cl1—O4	115.4 (3)	N2—C8—C7	130.7 (3)
O2—Cl1—O1	112.5 (3)	H1w1—O1w—H1w2	111 (2)
O4—Cl1—O1	108.4 (2)	H2w1—O2w—H2w2	109 (2)
O2—Cl1—O3	106.1 (3)	C2—N1—H1n	118 (3)
O4—Cl1—O3	107.2 (4)	C3—N1—H1n	133 (3)
O1—Cl1—O3	106.6 (3)	C2—N2—H2n	128 (2)
C2—N1—C3	109.3 (2)	C8—N2—H2n	123 (2)
C2—N2—C8	109.0 (3)	C1^i—C1—H1a	109.0
C1^i—C1—C2	112.7 (3)	C2—C1—H1a	109.0
N1—C2—N2	109.1 (3)	C1^i—C1—H1b	109.0
N1—C2—C1	124.6 (3)	C2—C1—H1b	109.0
N2—C2—C1	126.3 (3)	H1a—C1—H1b	107.8
C8—C3—C4	121.2 (3)	C5—C4—H4	121.7
C8—C3—N1	105.9 (2)	C3—C4—H4	121.7
C4—C3—N1	132.9 (3)	C4—C5—H5	118.9
C5—C4—C3	116.6 (3)	C6—C5—H5	118.9
C4—C5—C6	122.2 (3)	C7—C6—H6	119.4
C7—C6—C5	121.3 (3)	C5—C6—H6	119.4
C6—C7—C8	116.1 (3)	C6—C7—H7	122.0
C3—C8—N2	106.7 (3)	C8—C7—H7	122.0
C3—C8—C7	122.6 (3)
C3—N1—C2—N2	0.2 (4)	C4—C5—C6—C7	0.7 (6)
C3—N1—C2—C1	−176.9 (3)	C5—C6—C7—C8	−0.3 (6)
C8—N2—C2—N1	−0.3 (4)	C4—C3—C8—N2	179.9 (3)
C8—N2—C2—C1	176.8 (3)	N1—C3—C8—N2	−0.1 (4)
C1^i—C1—C2—N1	−149.3 (4)	C4—C3—C8—C7	0.0 (5)
C1^i—C1—C2—N2	34.1 (6)	N1—C3—C8—C7	179.9 (3)
C2—N1—C3—C8	0.0 (4)	C2—N2—C8—C3	0.2 (4)
C2—N1—C3—C4	179.9 (4)	C2—N2—C8—C7	−179.8 (4)
C8—C3—C4—C5	0.4 (5)	C6—C7—C8—C3	−0.1 (5)
N1—C3—C4—C5	−179.5 (3)	C6—C7—C8—N2	−180.0 (4)
C3—C4—C5—C6	−0.7 (6)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H1w1···O1	0.84 (1)	2.13 (2)	2.915 (4)	154 (4)
O1w—H1w2···O2w^i	0.84 (1)	2.29 (2)	3.083 (4)	158 (4)
O2w—H2w1···O1^ii	0.85 (1)	2.11 (2)	2.907 (4)	157 (5)
O2w—H2w2···O1w^iii	0.85 (1)	2.13 (4)	2.897 (4)	150 (7)
N1—H1n···O1w	0.85 (1)	2.02 (1)	2.853 (4)	169 (4)
N2—H2n···O2w	0.85 (1)	1.96 (1)	2.804 (4)	172 (3)

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