(Benzimidazol-3-ium-2-ylmeth­yl)(benzimidazol-2-ylmeth­yl)aminium sulfate

Meng, X.-G.; Mei, F.-S.; Liao, Z.-R.

doi:10.1107/S1600536805025109

(Benzimidazol-3-ium-2-ylmethyl)(benzimidazol-2-ylmethyl)aminium sulfate

X.-G. Meng, F.-S. Mei and Z.-R. Liao

In the title crystal structure, C₁₆H₁₇N₅²⁺·SO₄²⁻, cations and anions are linked via N—H

O hydrogen bonds, while ion pairs form extended one-dimensional chains through intermolecular N—H

N hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805025109/lh6484sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805025109/lh6484Isup2.hkl Contains datablock I

CCDC reference: 283954

checkCIF report

Key indicators

Single-crystal X-ray study
T = 292 K
Mean (C-C) = 0.004 Å
R factor = 0.060
wR factor = 0.170
Data-to-parameter ratio = 12.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         S1
PLAT416_ALERT_2_C Short Intra D-H..H-D       H1D    ..  H4A     ..       1.99 Ang.
PLAT420_ALERT_2_C D-H Without Acceptor       N1     -   H1C    ...          ?

   0 ALERT level A = In general: serious problem
   0 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
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

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: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

(Benzimidazol-3-ium-2-ylmethyl)(benzimidazol-2-ylmethyl)aminium sulfate top

Crystal data top

C₁₆H₁₇N₅²⁺·SO₄²⁻	F(000) = 784
M_r = 375.41	D_x = 1.475 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3387 reflections
a = 8.4723 (11) Å	θ = 2.6–23.2°
b = 13.7762 (18) Å	µ = 0.23 mm⁻¹
c = 14.8752 (19) Å	T = 292 K
β = 103.150 (2)°	Block, yellow
V = 1690.6 (4) Å³	0.30 × 0.20 × 0.18 mm
Z = 4

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2305 reflections with I > 2σ(I)
Radiation source: fine focus sealed Siemens Mo tube	R_int = 0.089
Graphite monochromator	θ_max = 25.0°, θ_min = 2.0°
0.3° wide ω scans	h = −10→10
11984 measured reflections	k = −16→16
2953 independent reflections	l = −17→17

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.171	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.099P)² + 0.3832P] where P = (F_o² + 2F_c²)/3
2953 reflections	(Δ/σ)_max < 0.001
235 parameters	Δρ_max = 0.58 e Å⁻³
0 restraints	Δρ_min = −0.42 e Å⁻³

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

	x	y	z	U_iso*/U_eq
S1	0.20702 (9)	0.83540 (5)	0.16792 (5)	0.0444 (3)
N3	0.7220 (3)	−0.08578 (15)	0.13282 (15)	0.0402 (6)
H3	0.7255	−0.1093	0.1868	0.048*
N4	1.0759 (3)	0.28640 (16)	0.05832 (15)	0.0445 (6)
H4A	1.0165	0.2457	0.0217	0.053*
N5	1.2160 (3)	0.35635 (17)	0.19057 (15)	0.0435 (6)
N2	0.7562 (3)	0.00817 (16)	0.02685 (14)	0.0400 (6)
H2	0.7868	0.0575	−0.0004	0.048*
C2	0.7902 (3)	−0.00433 (19)	0.11670 (18)	0.0378 (6)
C10	1.1231 (3)	0.28118 (19)	0.15045 (18)	0.0406 (7)
C1	0.8966 (4)	0.0620 (2)	0.18906 (19)	0.0475 (7)
H1A	0.8403	0.0762	0.2375	0.057*
H1B	0.9964	0.0284	0.2169	0.057*
N1	0.9335 (4)	0.14980 (19)	0.14920 (18)	0.0629 (8)
H1C	0.8488	0.1905	0.1440	0.075*
H1D	0.9464	0.1374	0.0919	0.075*
C16	1.2319 (4)	0.4136 (2)	0.11906 (19)	0.0428 (7)
C7	0.5555 (4)	−0.2168 (2)	0.0259 (2)	0.0499 (8)
H7	0.5402	−0.2585	0.0723	0.060*
C3	0.6629 (3)	−0.06984 (19)	−0.01959 (18)	0.0378 (6)
C8	0.6412 (3)	−0.12980 (19)	0.04863 (17)	0.0380 (6)
C11	1.1430 (3)	0.3709 (2)	0.03516 (19)	0.0415 (7)
C9	1.0811 (4)	0.1990 (2)	0.2022 (2)	0.0474 (7)
H9A	1.0626	0.2215	0.2607	0.057*
H9B	1.1705	0.1532	0.2150	0.057*
C5	0.5146 (4)	−0.1798 (2)	−0.1343 (2)	0.0543 (8)
H5	0.4733	−0.1964	−0.1958	0.065*
C4	0.5982 (4)	−0.0925 (2)	−0.11248 (19)	0.0472 (7)
H4	0.6108	−0.0500	−0.1589	0.057*
C6	0.4934 (4)	−0.2405 (2)	−0.0665 (2)	0.0535 (8)
H6	0.4371	−0.2984	−0.0817	0.064*
C12	1.1344 (4)	0.4112 (2)	−0.0482 (2)	0.0556 (8)
H12	1.0768	0.3835	−0.1029	0.067*
C13	1.2180 (5)	0.4969 (3)	−0.0456 (2)	0.0696 (10)
H13	1.2163	0.5286	−0.1011	0.084*
C15	1.3164 (5)	0.5002 (3)	0.1208 (2)	0.0634 (9)
H15	1.3746	0.5282	0.1752	0.076*
C14	1.3072 (5)	0.5398 (3)	0.0378 (3)	0.0759 (11)
H14	1.3613	0.5980	0.0343	0.091*
O3	0.0924 (3)	0.8737 (2)	0.08415 (16)	0.0789 (8)
O1	0.1905 (4)	0.7333 (2)	0.1661 (2)	0.1097 (11)
O2	0.3709 (4)	0.8587 (3)	0.1754 (2)	0.1118 (12)
O4	0.1679 (5)	0.8681 (3)	0.2440 (2)	0.1226 (13)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0537 (5)	0.0482 (5)	0.0431 (4)	0.0001 (3)	0.0135 (3)	0.0044 (3)
N3	0.0556 (15)	0.0381 (12)	0.0297 (12)	0.0001 (10)	0.0153 (10)	0.0049 (9)
N4	0.0569 (15)	0.0433 (13)	0.0340 (13)	−0.0092 (11)	0.0115 (11)	−0.0079 (10)
N5	0.0539 (15)	0.0474 (14)	0.0324 (12)	−0.0078 (11)	0.0166 (11)	−0.0066 (10)
N2	0.0538 (14)	0.0356 (12)	0.0321 (13)	−0.0028 (10)	0.0126 (10)	0.0051 (9)
C2	0.0482 (16)	0.0360 (14)	0.0301 (14)	0.0013 (12)	0.0104 (12)	0.0031 (11)
C10	0.0483 (17)	0.0437 (16)	0.0309 (15)	−0.0011 (12)	0.0116 (12)	−0.0043 (11)
C1	0.065 (2)	0.0433 (16)	0.0349 (16)	−0.0080 (14)	0.0121 (14)	−0.0017 (12)
N1	0.068 (2)	0.0575 (16)	0.0408 (15)	−0.0232 (15)	0.0091 (14)	0.0044 (12)
C16	0.0515 (17)	0.0434 (15)	0.0373 (16)	−0.0049 (13)	0.0182 (13)	−0.0049 (12)
C7	0.0588 (19)	0.0398 (16)	0.054 (2)	−0.0037 (13)	0.0190 (15)	0.0017 (13)
C3	0.0431 (15)	0.0385 (14)	0.0327 (15)	0.0023 (12)	0.0104 (12)	0.0005 (11)
C8	0.0450 (16)	0.0382 (14)	0.0318 (14)	0.0016 (12)	0.0110 (12)	−0.0019 (11)
C11	0.0462 (16)	0.0443 (16)	0.0360 (15)	0.0000 (12)	0.0133 (12)	−0.0018 (12)
C9	0.0578 (19)	0.0485 (16)	0.0373 (16)	−0.0053 (14)	0.0135 (14)	0.0003 (13)
C5	0.058 (2)	0.061 (2)	0.0411 (18)	0.0027 (15)	0.0058 (15)	−0.0142 (15)
C4	0.0570 (19)	0.0512 (17)	0.0337 (16)	−0.0003 (14)	0.0112 (14)	0.0002 (13)
C6	0.0575 (19)	0.0434 (16)	0.058 (2)	−0.0081 (14)	0.0099 (16)	−0.0094 (15)
C12	0.074 (2)	0.0601 (19)	0.0335 (17)	−0.0019 (16)	0.0132 (15)	0.0003 (14)
C13	0.095 (3)	0.069 (2)	0.052 (2)	−0.013 (2)	0.030 (2)	0.0148 (17)
C15	0.079 (2)	0.063 (2)	0.0494 (19)	−0.0264 (18)	0.0183 (17)	−0.0114 (16)
C14	0.096 (3)	0.067 (2)	0.070 (3)	−0.032 (2)	0.029 (2)	0.0062 (19)
O3	0.0858 (19)	0.0960 (19)	0.0550 (15)	0.0050 (15)	0.0162 (13)	0.0249 (14)
O1	0.140 (3)	0.0643 (19)	0.114 (3)	−0.0139 (17)	0.005 (2)	0.0116 (16)
O2	0.072 (2)	0.127 (3)	0.142 (3)	−0.0069 (18)	0.0372 (19)	0.037 (2)
O4	0.151 (3)	0.160 (3)	0.0608 (18)	0.046 (3)	0.0341 (19)	−0.013 (2)

Geometric parameters (Å, º) top

S1—O4	1.329 (3)	C16—C15	1.388 (4)
S1—O2	1.404 (3)	C16—C11	1.430 (4)
S1—O1	1.413 (3)	C7—C6	1.395 (4)
S1—O3	1.491 (2)	C7—C8	1.402 (4)
N3—C2	1.309 (3)	C7—H7	0.9300
N3—C8	1.419 (3)	C3—C8	1.353 (4)
N3—H3	0.8600	C3—C4	1.401 (4)
N4—C10	1.339 (3)	C11—C12	1.346 (4)
N4—C11	1.373 (4)	C9—H9A	0.9700
N4—H4A	0.8600	C9—H9B	0.9700
N5—C10	1.354 (3)	C5—C6	1.353 (4)
N5—C16	1.355 (3)	C5—C4	1.397 (4)
N2—C2	1.313 (3)	C5—H5	0.9300
N2—C3	1.417 (3)	C4—H4	0.9300
N2—H2	0.8600	C6—H6	0.9300
C2—C1	1.537 (4)	C12—C13	1.372 (5)
C10—C9	1.458 (4)	C12—H12	0.9300
C1—N1	1.414 (4)	C13—C14	1.427 (5)
C1—H1A	0.9700	C13—H13	0.9300
C1—H1B	0.9700	C15—C14	1.336 (5)
N1—C9	1.482 (4)	C15—H15	0.9300
N1—H1C	0.9000	C14—H14	0.9300
N1—H1D	0.9000

O4—S1—O2	106.8 (3)	C6—C7—H7	120.1
O4—S1—O1	108.1 (2)	C8—C7—H7	120.1
O2—S1—O1	108.7 (2)	C8—C3—C4	121.0 (3)
O4—S1—O3	110.6 (2)	C8—C3—N2	104.7 (2)
O2—S1—O3	115.40 (17)	C4—C3—N2	134.4 (2)
O1—S1—O3	107.05 (18)	C3—C8—C7	119.5 (3)
C2—N3—C8	110.4 (2)	C3—C8—N3	106.3 (2)
C2—N3—H3	124.8	C7—C8—N3	134.2 (2)
C8—N3—H3	124.8	C12—C11—N4	130.0 (3)
C10—N4—C11	104.9 (2)	C12—C11—C16	122.8 (3)
C10—N4—H4A	127.5	N4—C11—C16	107.2 (2)
C11—N4—H4A	127.5	C10—C9—N1	110.6 (2)
C10—N5—C16	104.5 (2)	C10—C9—H9A	109.5
C2—N2—C3	111.4 (2)	N1—C9—H9A	109.5
C2—N2—H2	124.3	C10—C9—H9B	109.5
C3—N2—H2	124.3	N1—C9—H9B	109.5
N3—C2—N2	107.2 (2)	H9A—C9—H9B	108.1
N3—C2—C1	126.4 (2)	C6—C5—C4	120.4 (3)
N2—C2—C1	126.3 (2)	C6—C5—H5	119.8
N4—C10—N5	114.7 (2)	C4—C5—H5	119.8
N4—C10—C9	122.0 (2)	C5—C4—C3	119.0 (3)
N5—C10—C9	123.2 (2)	C5—C4—H4	120.5
N1—C1—C2	111.4 (2)	C3—C4—H4	120.5
N1—C1—H1A	109.3	C5—C6—C7	120.4 (3)
C2—C1—H1A	109.3	C5—C6—H6	119.8
N1—C1—H1B	109.3	C7—C6—H6	119.8
C2—C1—H1B	109.3	C11—C12—C13	114.2 (3)
H1A—C1—H1B	108.0	C11—C12—H12	122.9
C1—N1—C9	114.1 (2)	C13—C12—H12	122.9
C1—N1—H1C	108.7	C12—C13—C14	123.3 (3)
C9—N1—H1C	108.7	C12—C13—H13	118.4
C1—N1—H1D	108.7	C14—C13—H13	118.4
C9—N1—H1D	108.7	C14—C15—C16	114.4 (3)
H1C—N1—H1D	107.6	C14—C15—H15	122.8
N5—C16—C15	128.9 (3)	C16—C15—H15	122.8
N5—C16—C11	108.6 (2)	C15—C14—C13	122.9 (3)
C15—C16—C11	122.5 (3)	C15—C14—H14	118.6
C6—C7—C8	119.8 (3)	C13—C14—H14	118.6

C8—N3—C2—N2	1.1 (3)	C2—N3—C8—C7	177.4 (3)
C8—N3—C2—C1	−176.4 (3)	C10—N4—C11—C12	179.9 (3)
C3—N2—C2—N3	−1.1 (3)	C10—N4—C11—C16	0.2 (3)
C3—N2—C2—C1	176.4 (3)	N5—C16—C11—C12	179.5 (3)
C11—N4—C10—N5	0.4 (3)	C15—C16—C11—C12	−0.1 (5)
C11—N4—C10—C9	−177.7 (3)	N5—C16—C11—N4	−0.8 (3)
C16—N5—C10—N4	−0.9 (3)	C15—C16—C11—N4	179.6 (3)
C16—N5—C10—C9	177.2 (3)	N4—C10—C9—N1	−23.9 (4)
N3—C2—C1—N1	−172.6 (3)	N5—C10—C9—N1	158.2 (3)
N2—C2—C1—N1	10.3 (4)	C1—N1—C9—C10	172.2 (3)
C2—C1—N1—C9	−157.4 (3)	C6—C5—C4—C3	1.4 (5)
C10—N5—C16—C15	−179.4 (3)	C8—C3—C4—C5	−2.0 (4)
C10—N5—C16—C11	1.0 (3)	N2—C3—C4—C5	177.7 (3)
C2—N2—C3—C8	0.7 (3)	C4—C5—C6—C7	−0.3 (5)
C2—N2—C3—C4	−179.0 (3)	C8—C7—C6—C5	−0.4 (4)
C4—C3—C8—C7	1.3 (4)	N4—C11—C12—C13	−179.7 (3)
N2—C3—C8—C7	−178.5 (2)	C16—C11—C12—C13	−0.1 (5)
C4—C3—C8—N3	179.7 (2)	C11—C12—C13—C14	0.3 (5)
N2—C3—C8—N3	−0.1 (3)	N5—C16—C15—C14	−179.4 (3)
C6—C7—C8—C3	−0.1 (4)	C11—C16—C15—C14	0.2 (5)
C6—C7—C8—N3	−178.0 (3)	C16—C15—C14—C13	0.0 (6)
C2—N3—C8—C3	−0.6 (3)	C12—C13—C14—C15	−0.2 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1D···O3ⁱ	0.90	2.57	3.443 (4)	164
N2—H2···O3ⁱ	0.86	2.02	2.825 (3)	156
N4—H4A···O3ⁱ	0.86	2.32	3.165 (4)	168
N3—H3···N5ⁱⁱ	0.86	1.84	2.681 (3)	165

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

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(Benzimidazol-3-ium-2-ylmeth­yl)(benzimidazol-2-ylmeth­yl)aminium sulfate

Supporting information

Key indicators

checkCIF/PLATON results

(Benzimidazol-3-ium-2-ylmethyl)(benzimidazol-2-ylmethyl)aminium sulfate