2,2′-(Propane-1,3-di­yl)bis­(benzimidazolium) dichloride dihydrate

In the title compound, C₁₇H₁₈N₄²⁺·2Cl⁻·2H₂O, anions, cations and water mol­ecules are linked into a two-dimensional framework by a combination of inter­molecular N—H...O, N—H...Cl and O—H...Cl hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.053
• wR factor = 0.134
• Data-to-parameter ratio = 17.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C17 H18 N4
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              H2 O
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          3
              H2 O
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          4
              Cl
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          5
              Cl

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 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
   0 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
   5 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); 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, 2000); software used to prepare material for publication: SHELXTL.

2,2'-(Propane-1,3-diyl)bis(benzimidazolium) dichloride dihydrate

Crystal data

C17H18N4^2+·2Cl^−·2H2O	F(000) = 808
Mr = 385.29	Dx = 1.378 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3278 reflections
a = 9.6420 (8) Å	θ = 2.5–24.0°
b = 13.6336 (11) Å	µ = 0.37 mm^−1
c = 16.9921 (10) Å	T = 298 K
β = 123.729 (3)°	Block, red
V = 1857.7 (2) Å^3	0.35 × 0.22 × 0.20 mm
Z = 4

Data collection

Bruker SMART CCD diffractometer	4242 independent reflections
Radiation source: fine-focus sealed tube	3203 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
φ and ω scans	θmax = 27.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −12→12
Tmin = 0.882, Tmax = 0.930	k = −17→15
13103 measured 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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.134	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0648P)^2 + 0.3667P] where P = (Fo^2 + 2Fc^2)/3
4242 reflections	(Δ/σ)max < 0.001
250 parameters	Δρmax = 0.30 e Å^−3
8 restraints	Δρmin = −0.22 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
C1	0.3115 (3)	−0.60351 (15)	−0.59230 (15)	0.0372 (5)
C2	0.3496 (3)	−0.59444 (17)	−0.65953 (17)	0.0454 (6)
H2	0.4585	−0.5999	−0.6436	0.054*
C3	0.2184 (3)	−0.57692 (18)	−0.75093 (17)	0.0484 (6)
H3	0.2392	−0.5695	−0.7979	0.058*
C4	0.0548 (3)	−0.57004 (17)	−0.77509 (16)	0.0467 (6)
H4	−0.0305	−0.5591	−0.8380	0.056*
C5	0.0158 (3)	−0.57894 (16)	−0.70902 (16)	0.0418 (5)
H5	−0.0934	−0.5742	−0.7254	0.050*
C6	0.1483 (3)	−0.59545 (15)	−0.61663 (15)	0.0357 (5)
C7	0.3119 (3)	−0.62306 (16)	−0.46199 (15)	0.0388 (5)
C8	0.3793 (3)	−0.63760 (19)	−0.36060 (15)	0.0444 (5)
H8A	0.4534	−0.5833	−0.3255	0.053*
H8B	0.4461	−0.6969	−0.3397	0.053*
C9	0.2522 (3)	−0.64556 (18)	−0.33426 (15)	0.0412 (5)
H9A	0.1799	−0.5886	−0.3571	0.049*
H9B	0.1839	−0.7036	−0.3630	0.049*
C10	0.3460 (3)	−0.65189 (18)	−0.22719 (15)	0.0435 (5)
H10A	0.4129	−0.7112	−0.2065	0.052*
H10B	0.4220	−0.5966	−0.2000	0.052*
C11	0.2407 (3)	−0.65251 (15)	−0.18869 (15)	0.0372 (5)
C12	0.0270 (3)	−0.66788 (15)	−0.17368 (14)	0.0370 (5)
C13	−0.1257 (3)	−0.68406 (18)	−0.18668 (17)	0.0472 (6)
H13	−0.2182	−0.7041	−0.2447	0.057*
C14	−0.1338 (3)	−0.6690 (2)	−0.10952 (19)	0.0551 (6)
H14	−0.2348	−0.6787	−0.1155	0.066*
C15	0.0052 (3)	−0.6397 (2)	−0.02228 (18)	0.0563 (7)
H15	−0.0058	−0.6301	0.0282	0.068*
C16	0.1581 (3)	−0.62442 (19)	−0.00874 (16)	0.0497 (6)
H16	0.2508	−0.6050	0.0495	0.060*
C17	0.1664 (3)	−0.63956 (16)	−0.08673 (15)	0.0383 (5)
N1	0.0796 (2)	−0.67465 (14)	−0.23475 (12)	0.0383 (4)
H1A	0.013 (3)	−0.6856 (18)	−0.2937 (8)	0.057*
N2	0.2961 (2)	−0.63128 (14)	−0.09921 (12)	0.0395 (4)
H2A	0.3961 (16)	−0.6132 (17)	−0.0573 (14)	0.059*
N3	0.4088 (2)	−0.62121 (15)	−0.49579 (13)	0.0422 (4)
H3A	0.5140 (14)	−0.6337 (19)	−0.4667 (17)	0.063*
N4	0.1556 (2)	−0.60810 (13)	−0.53303 (13)	0.0367 (4)
H4A	0.068 (2)	−0.6020 (17)	−0.5317 (18)	0.055*
Cl1	0.76241 (7)	−0.69346 (5)	−0.43757 (4)	0.0570 (2)
Cl2	−0.43239 (8)	−0.61008 (5)	−0.77954 (4)	0.0584 (2)
O1	−0.1503 (2)	−0.58483 (14)	−0.56536 (12)	0.0512 (4)
H1C	−0.171 (4)	−0.6160 (19)	−0.5316 (19)	0.077*
H1B	−0.227 (3)	−0.595 (2)	−0.6207 (10)	0.077*
O2	−0.3857 (2)	−0.59773 (15)	−0.94919 (14)	0.0631 (5)
H2B	−0.336 (4)	−0.6481 (16)	−0.944 (3)	0.095*
H2C	−0.397 (5)	−0.595 (2)	−0.9051 (18)	0.095*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0361 (11)	0.0404 (12)	0.0363 (11)	−0.0026 (9)	0.0208 (10)	−0.0028 (9)
C2	0.0462 (13)	0.0552 (14)	0.0469 (14)	−0.0050 (10)	0.0335 (12)	−0.0032 (11)
C3	0.0602 (15)	0.0525 (15)	0.0445 (13)	−0.0046 (11)	0.0365 (13)	−0.0004 (11)
C4	0.0535 (14)	0.0468 (14)	0.0377 (12)	0.0021 (11)	0.0241 (11)	0.0013 (10)
C5	0.0410 (12)	0.0418 (12)	0.0418 (12)	0.0040 (9)	0.0225 (11)	0.0008 (10)
C6	0.0410 (11)	0.0341 (11)	0.0382 (12)	−0.0029 (9)	0.0258 (10)	−0.0036 (9)
C7	0.0374 (11)	0.0412 (12)	0.0406 (12)	−0.0014 (9)	0.0234 (10)	−0.0020 (9)
C8	0.0367 (11)	0.0588 (15)	0.0357 (12)	0.0003 (10)	0.0189 (10)	0.0029 (10)
C9	0.0397 (11)	0.0496 (13)	0.0356 (12)	−0.0041 (10)	0.0218 (10)	−0.0014 (10)
C10	0.0384 (11)	0.0522 (14)	0.0380 (12)	−0.0047 (10)	0.0200 (10)	0.0026 (10)
C11	0.0410 (11)	0.0347 (11)	0.0329 (11)	−0.0014 (9)	0.0186 (10)	0.0019 (9)
C12	0.0383 (11)	0.0373 (12)	0.0330 (11)	0.0006 (9)	0.0184 (10)	0.0019 (9)
C13	0.0386 (12)	0.0555 (15)	0.0408 (13)	−0.0027 (10)	0.0178 (10)	0.0023 (11)
C14	0.0468 (14)	0.0687 (17)	0.0571 (16)	0.0015 (12)	0.0334 (13)	0.0040 (13)
C15	0.0629 (16)	0.0717 (18)	0.0472 (15)	0.0058 (13)	0.0386 (13)	0.0008 (13)
C16	0.0489 (13)	0.0638 (16)	0.0329 (12)	0.0006 (11)	0.0205 (11)	−0.0049 (11)
C17	0.0400 (11)	0.0376 (12)	0.0345 (11)	−0.0007 (9)	0.0189 (10)	0.0016 (9)
N1	0.0352 (9)	0.0464 (11)	0.0262 (9)	−0.0040 (8)	0.0127 (8)	−0.0015 (8)
N2	0.0343 (9)	0.0487 (11)	0.0280 (9)	−0.0050 (8)	0.0125 (8)	−0.0022 (8)
N3	0.0331 (9)	0.0576 (12)	0.0384 (11)	−0.0009 (9)	0.0213 (9)	−0.0010 (9)
N4	0.0342 (9)	0.0453 (11)	0.0364 (10)	0.0029 (8)	0.0233 (8)	0.0011 (8)
Cl1	0.0350 (3)	0.0907 (5)	0.0406 (3)	−0.0032 (3)	0.0181 (3)	0.0068 (3)
Cl2	0.0439 (3)	0.0752 (5)	0.0475 (4)	0.0014 (3)	0.0201 (3)	−0.0038 (3)
O1	0.0421 (9)	0.0670 (12)	0.0458 (10)	−0.0040 (8)	0.0252 (8)	−0.0010 (9)
O2	0.0467 (10)	0.0751 (14)	0.0499 (11)	0.0022 (9)	0.0158 (9)	−0.0025 (10)

Geometric parameters (Å, º)

C1—N3	1.385 (3)	C10—H10B	0.9700
C1—C2	1.387 (3)	C11—N1	1.329 (3)
C1—C6	1.392 (3)	C11—N2	1.334 (3)
C2—C3	1.374 (3)	C12—C13	1.380 (3)
C2—H2	0.9300	C12—N1	1.388 (3)
C3—C4	1.395 (3)	C12—C17	1.390 (3)
C3—H3	0.9300	C13—C14	1.371 (3)
C4—C5	1.374 (3)	C13—H13	0.9300
C4—H4	0.9300	C14—C15	1.396 (4)
C5—C6	1.386 (3)	C14—H14	0.9300
C5—H5	0.9300	C15—C16	1.376 (3)
C6—N4	1.393 (3)	C15—H15	0.9300
C7—N4	1.322 (3)	C16—C17	1.387 (3)
C7—N3	1.342 (3)	C16—H16	0.9300
C7—C8	1.479 (3)	C17—N2	1.384 (3)
C8—C9	1.524 (3)	N1—H1A	0.851 (12)
C8—H8A	0.9700	N2—H2A	0.86 (3)
C8—H8B	0.9700	N3—H3A	0.86 (3)
C9—C10	1.519 (3)	N4—H4A	0.86 (3)
C9—H9A	0.9700	O1—H1C	0.82 (3)
C9—H9B	0.9700	O1—H1B	0.82 (3)
C10—C11	1.482 (3)	O2—H2B	0.81 (3)
C10—H10A	0.9700	O2—H2C	0.82 (3)
N3—C1—C2	132.5 (2)	C9—C10—H10B	108.4
N3—C1—C6	106.06 (18)	H10A—C10—H10B	107.5
C2—C1—C6	121.5 (2)	N1—C11—N2	108.52 (18)
C3—C2—C1	116.6 (2)	N1—C11—C10	127.19 (19)
C3—C2—H2	121.7	N2—C11—C10	124.28 (19)
C1—C2—H2	121.7	C13—C12—N1	132.1 (2)
C2—C3—C4	121.7 (2)	C13—C12—C17	122.0 (2)
C2—C3—H3	119.2	N1—C12—C17	105.89 (18)
C4—C3—H3	119.2	C14—C13—C12	116.4 (2)
C5—C4—C3	122.1 (2)	C14—C13—H13	121.8
C5—C4—H4	118.9	C12—C13—H13	121.8
C3—C4—H4	118.9	C13—C14—C15	121.8 (2)
C4—C5—C6	116.2 (2)	C13—C14—H14	119.1
C4—C5—H5	121.9	C15—C14—H14	119.1
C6—C5—H5	121.9	C16—C15—C14	121.9 (2)
C5—C6—C1	121.91 (19)	C16—C15—H15	119.0
C5—C6—N4	131.9 (2)	C14—C15—H15	119.0
C1—C6—N4	106.15 (18)	C15—C16—C17	116.3 (2)
N4—C7—N3	108.51 (18)	C15—C16—H16	121.9
N4—C7—C8	128.71 (19)	C17—C16—H16	121.9
N3—C7—C8	122.76 (19)	N2—C17—C16	132.1 (2)
C7—C8—C9	116.53 (18)	N2—C17—C12	106.41 (18)
C7—C8—H8A	108.2	C16—C17—C12	121.5 (2)
C9—C8—H8A	108.2	C11—N1—C12	109.72 (17)
C7—C8—H8B	108.2	C11—N1—H1A	127.2 (17)
C9—C8—H8B	108.2	C12—N1—H1A	122.8 (17)
H8A—C8—H8B	107.3	C11—N2—C17	109.46 (18)
C10—C9—C8	108.35 (18)	C11—N2—H2A	124.2 (18)
C10—C9—H9A	110.0	C17—N2—H2A	126.3 (18)
C8—C9—H9A	110.0	C7—N3—C1	109.56 (17)
C10—C9—H9B	110.0	C7—N3—H3A	128.9 (18)
C8—C9—H9B	110.0	C1—N3—H3A	121.3 (18)
H9A—C9—H9B	108.4	C7—N4—C6	109.71 (17)
C11—C10—C9	115.52 (18)	C7—N4—H4A	128.9 (18)
C11—C10—H10A	108.4	C6—N4—H4A	121.3 (18)
C9—C10—H10A	108.4	H1C—O1—H1B	107 (3)
C11—C10—H10B	108.4	H2B—O2—H2C	108 (3)
N3—C1—C2—C3	179.7 (2)	C15—C16—C17—N2	179.9 (2)
C6—C1—C2—C3	0.1 (3)	C15—C16—C17—C12	0.4 (4)
C1—C2—C3—C4	−0.9 (4)	C13—C12—C17—N2	179.3 (2)
C2—C3—C4—C5	0.9 (4)	N1—C12—C17—N2	−0.4 (2)
C3—C4—C5—C6	−0.1 (3)	C13—C12—C17—C16	−1.1 (3)
C4—C5—C6—C1	−0.6 (3)	N1—C12—C17—C16	179.1 (2)
C4—C5—C6—N4	−179.9 (2)	N2—C11—N1—C12	0.0 (2)
N3—C1—C6—C5	−179.0 (2)	C10—C11—N1—C12	179.2 (2)
C2—C1—C6—C5	0.6 (3)	C13—C12—N1—C11	−179.4 (2)
N3—C1—C6—N4	0.4 (2)	C17—C12—N1—C11	0.3 (2)
C2—C1—C6—N4	−179.9 (2)	N1—C11—N2—C17	−0.2 (2)
N4—C7—C8—C9	6.0 (4)	C10—C11—N2—C17	−179.5 (2)
N3—C7—C8—C9	−175.6 (2)	C16—C17—N2—C11	−179.1 (2)
C7—C8—C9—C10	−175.5 (2)	C12—C17—N2—C11	0.4 (2)
C8—C9—C10—C11	175.6 (2)	N4—C7—N3—C1	0.5 (3)
C9—C10—C11—N1	19.8 (3)	C8—C7—N3—C1	−178.2 (2)
C9—C10—C11—N2	−161.1 (2)	C2—C1—N3—C7	179.8 (2)
N1—C12—C13—C14	−179.3 (2)	C6—C1—N3—C7	−0.6 (2)
C17—C12—C13—C14	1.1 (3)	N3—C7—N4—C6	−0.3 (2)
C12—C13—C14—C15	−0.5 (4)	C8—C7—N4—C6	178.4 (2)
C13—C14—C15—C16	−0.2 (4)	C5—C6—N4—C7	179.3 (2)
C14—C15—C16—C17	0.2 (4)	C1—C6—N4—C7	−0.1 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl1^i	0.85 (1)	2.30 (1)	3.0971 (18)	157 (2)
N2—H2A···O2^ii	0.86 (3)	1.89 (1)	2.726 (3)	167 (2)
N3—H3A···Cl1	0.86 (3)	2.31 (1)	3.1349 (19)	160 (2)
N4—H4A···O1	0.86 (3)	1.86 (3)	2.703 (2)	164 (3)
O1—H1C···Cl1^i	0.82 (3)	2.29 (3)	3.1055 (18)	176 (3)
O1—H1B···Cl2	0.82 (3)	2.31 (1)	3.1253 (19)	174 (3)
O2—H2B···Cl1^iii	0.81 (3)	2.34 (3)	3.142 (2)	170 (4)
O2—H2C···Cl2	0.82 (4)	2.35 (4)	3.159 (2)	172 (3)

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