Literature DB >> 21588139

Bis(1-benzyl-piperazine-1,4-diium) hexa-chloridocadmate(II) dihydrate.

Meher El Glaoui, Matthias Zeller, Erwann Jeanneau, Cherif Ben Nasr.

Abstract

The asymmetric unit of the title compound, (C(11)H(18)N(2))(2)[CdCl(6)]·2H(2)O, consists of one 1-benzyl-piperazine-1,4-diium dication, one water mol-ecule and one-half of a [CdCl(6)](4-) anion, located on an inversion centre. The crystal packing is governed by an extensive three-dimensional network of inter-molecular O-H⋯Cl, C-H⋯Cl, N-H⋯O and N-H⋯Cl hydrogen bonds, two of them bifurcated.

Entities: Chemical Disease Gene

Year: 2010 PMID： 21588139 PMCID： PMC3007331 DOI： 10.1107/S1600536810026073

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For meta-chlorido complexes, see: El Glaoui, Jeanneau, et al. (2009 ▶); El Glaoui, Kefi et al. (2009 ▶). For the role of C—H⋯Cl hydrogen bonds, see: Janiak & Scharmann (2003 ▶. For a discussion of Cd—Cl distances and Cl—Cd—Cl bond angles, see: Bala et al. (2006 ▶).

Experimental

Crystal data

(C11H18N2)2[CdCl6]·2H2O M = 717.68 Monoclinic, a = 12.734 (2) Å b = 9.1686 (14) Å c = 13.216 (2) Å β = 103.249 (3)° V = 1502.0 (4) Å3 Z = 2 Mo Kα radiation μ = 1.29 mm−1 T = 100 K 0.55 × 0.45 × 0.25 mm

Data collection

Bruker SMART APEX CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.622, T max = 0.746 11244 measured reflections 4446 independent reflections 4123 reflections with I > 2σ(I) R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.022 wR(F 2) = 0.057 S = 1.07 4446 reflections 172 parameters 3 restraints H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.51 e Å−3 Δρmin = −0.83 e Å−3 Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXTL. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810026073/hb5541sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810026073/hb5541Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

(C₁₁H₁₈N₂)₂[CdCl₆]·2H₂O	F(000) = 732
M_r = 717.68	D_x = 1.587 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2788 reflections
a = 12.734 (2) Å	θ = 2.7–31.0°
b = 9.1686 (14) Å	µ = 1.29 mm⁻¹
c = 13.216 (2) Å	T = 100 K
β = 103.249 (3)°	Plate, colourless
V = 1502.0 (4) Å³	0.55 × 0.45 × 0.25 mm
Z = 2

Bruker SMART APEX CCD diffractometer	4446 independent reflections
Radiation source: fine-focus sealed tube	4123 reflections with I > 2σ(I)
graphite	R_int = 0.016
ω scans	θ_max = 31.3°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −17→18
T_min = 0.622, T_max = 0.746	k = −12→13
11244 measured reflections	l = −18→19

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)] = 0.022	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.057	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.0269P)² + 0.6306P] where P = (F_o² + 2F_c²)/3
4446 reflections	(Δ/σ)_max = 0.001
172 parameters	Δρ_max = 0.51 e Å⁻³
3 restraints	Δρ_min = −0.83 e Å⁻³

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.

	x	y	z	U_iso*/U_eq
C1	0.03492 (12)	0.81561 (17)	0.11848 (12)	0.0242 (3)
H1C	0.0759	0.7794	0.0722	0.029*
C2	−0.07139 (13)	0.85867 (19)	0.08024 (14)	0.0312 (3)
H2	−0.1032	0.8503	0.0081	0.037*
C3	−0.13120 (12)	0.91374 (16)	0.14687 (15)	0.0292 (3)
H3	−0.2032	0.9457	0.1202	0.035*
C4	−0.08597 (12)	0.92209 (16)	0.25191 (14)	0.0269 (3)
H4	−0.1272	0.9588	0.2978	0.032*
C5	0.01972 (11)	0.87702 (15)	0.29110 (12)	0.0213 (3)
H5	0.0500	0.8814	0.3637	0.026*
C6	0.08142 (10)	0.82535 (13)	0.22417 (11)	0.0164 (2)
C7	0.19878 (10)	0.78999 (13)	0.26364 (11)	0.0156 (2)
H7A	0.2267	0.7431	0.2076	0.019*
H7B	0.2074	0.7203	0.3222	0.019*
C8	0.23911 (10)	1.04936 (12)	0.22283 (10)	0.0125 (2)
H8A	0.1609	1.0712	0.2067	0.015*
H8B	0.2591	1.0205	0.1575	0.015*
C9	0.30187 (10)	1.18282 (12)	0.26720 (10)	0.0122 (2)
H9A	0.2858	1.2635	0.2162	0.015*
H9B	0.2795	1.2138	0.3309	0.015*
C10	0.44650 (10)	1.02741 (13)	0.36618 (10)	0.0120 (2)
H10A	0.4307	1.0540	0.4337	0.014*
H10B	0.5244	1.0051	0.3782	0.014*
C11	0.38168 (9)	0.89435 (12)	0.32287 (10)	0.0116 (2)
H11A	0.4022	0.8627	0.2584	0.014*
H11B	0.3981	0.8137	0.3738	0.014*
Cd1	0.5000	0.5000	0.5000	0.01071 (4)
Cl1	0.36321 (2)	0.69672 (3)	0.55240 (2)	0.01362 (6)
Cl2	0.59831 (3)	0.49308 (3)	0.69137 (2)	0.01174 (6)
Cl3	0.37573 (2)	0.28368 (3)	0.54229 (2)	0.01263 (6)
N1	0.26320 (8)	0.92695 (11)	0.29971 (8)	0.01118 (18)
N2	0.41977 (8)	1.15258 (10)	0.29270 (8)	0.01172 (19)
H2A	0.4565	1.2342	0.3221	0.014*
H2B	0.4416	1.1317	0.2326	0.014*
O1	0.23289 (9)	0.99157 (10)	0.49769 (9)	0.0180 (2)
H1	0.2483 (14)	0.9558 (19)	0.3591 (12)	0.018 (4)*
H1A	0.2690 (17)	0.924 (2)	0.5315 (17)	0.044 (6)*
H1B	0.2655 (18)	1.066 (2)	0.5229 (18)	0.047 (7)*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0181 (7)	0.0284 (7)	0.0253 (7)	−0.0036 (5)	0.0031 (6)	−0.0025 (6)
C2	0.0203 (7)	0.0358 (8)	0.0323 (9)	−0.0051 (6)	−0.0049 (6)	0.0040 (7)
C3	0.0131 (6)	0.0210 (6)	0.0504 (10)	−0.0028 (5)	0.0008 (6)	0.0050 (6)
C4	0.0169 (7)	0.0201 (6)	0.0458 (10)	−0.0028 (5)	0.0117 (6)	−0.0048 (6)
C5	0.0166 (6)	0.0208 (6)	0.0274 (7)	−0.0038 (5)	0.0068 (5)	−0.0034 (5)
C6	0.0113 (6)	0.0134 (5)	0.0241 (7)	−0.0034 (4)	0.0033 (5)	−0.0013 (5)
C7	0.0132 (6)	0.0106 (5)	0.0223 (6)	−0.0020 (4)	0.0027 (5)	−0.0012 (4)
C8	0.0126 (5)	0.0112 (5)	0.0129 (6)	0.0007 (4)	0.0013 (4)	0.0025 (4)
C9	0.0122 (5)	0.0106 (5)	0.0144 (5)	0.0007 (4)	0.0042 (4)	0.0005 (4)
C10	0.0114 (5)	0.0129 (5)	0.0111 (6)	0.0004 (4)	0.0014 (4)	0.0004 (4)
C11	0.0096 (5)	0.0116 (5)	0.0136 (5)	0.0017 (4)	0.0028 (4)	0.0007 (4)
Cd1	0.01320 (7)	0.00972 (6)	0.00955 (7)	−0.00012 (4)	0.00332 (5)	0.00002 (4)
Cl1	0.01548 (14)	0.01289 (12)	0.01327 (13)	0.00202 (10)	0.00489 (11)	0.00058 (10)
Cl2	0.01277 (14)	0.01112 (12)	0.01138 (14)	−0.00071 (8)	0.00289 (11)	0.00010 (9)
Cl3	0.01428 (13)	0.01192 (12)	0.01209 (13)	−0.00170 (9)	0.00382 (10)	−0.00078 (9)
N1	0.0112 (5)	0.0100 (4)	0.0127 (5)	−0.0004 (3)	0.0032 (4)	0.0003 (4)
N2	0.0119 (5)	0.0110 (4)	0.0131 (5)	−0.0008 (3)	0.0046 (4)	−0.0005 (4)
O1	0.0185 (5)	0.0165 (4)	0.0190 (5)	0.0001 (3)	0.0046 (4)	−0.0001 (3)

C1—C2	1.389 (2)	C9—H9A	0.9900
C1—C6	1.390 (2)	C9—H9B	0.9900
C1—H1C	0.9500	C10—N2	1.4915 (16)
C2—C3	1.385 (3)	C10—C11	1.5102 (17)
C2—H2	0.9500	C10—H10A	0.9900
C3—C4	1.378 (3)	C10—H10B	0.9900
C3—H3	0.9500	C11—N1	1.4992 (15)
C4—C5	1.390 (2)	C11—H11A	0.9900
C4—H4	0.9500	C11—H11B	0.9900
C5—C6	1.3938 (19)	Cd1—Cl2ⁱ	2.5528 (5)
C5—H5	0.9500	Cd1—Cl2	2.5528 (5)
C6—C7	1.5012 (18)	Cd1—Cl3	2.6751 (4)
C7—N1	1.5158 (15)	Cd1—Cl3ⁱ	2.6751 (4)
C7—H7A	0.9900	Cd1—Cl1ⁱ	2.7055 (4)
C7—H7B	0.9900	Cd1—Cl1	2.7055 (4)
C8—N1	1.4978 (15)	N1—H1	0.889 (14)
C8—C9	1.5051 (16)	N2—H2A	0.9200
C8—H8A	0.9900	N2—H2B	0.9200
C8—H8B	0.9900	O1—H1A	0.837 (16)
C9—N2	1.4875 (15)	O1—H1B	0.830 (16)

C2—C1—C6	120.17 (15)	C11—C10—H10A	109.5
C2—C1—H1C	119.9	N2—C10—H10B	109.5
C6—C1—H1C	119.9	C11—C10—H10B	109.5
C3—C2—C1	120.28 (16)	H10A—C10—H10B	108.1
C3—C2—H2	119.9	N1—C11—C10	110.70 (9)
C1—C2—H2	119.9	N1—C11—H11A	109.5
C4—C3—C2	119.81 (14)	C10—C11—H11A	109.5
C4—C3—H3	120.1	N1—C11—H11B	109.5
C2—C3—H3	120.1	C10—C11—H11B	109.5
C3—C4—C5	120.30 (15)	H11A—C11—H11B	108.1
C3—C4—H4	119.8	Cl2ⁱ—Cd1—Cl2	180.0
C5—C4—H4	119.8	Cl2ⁱ—Cd1—Cl3	92.646 (11)
C4—C5—C6	120.22 (14)	Cl2—Cd1—Cl3	87.354 (11)
C4—C5—H5	119.9	Cl2ⁱ—Cd1—Cl3ⁱ	87.354 (11)
C6—C5—H5	119.9	Cl2—Cd1—Cl3ⁱ	92.646 (11)
C1—C6—C5	119.18 (13)	Cl3—Cd1—Cl3ⁱ	180.0
C1—C6—C7	119.76 (12)	Cl2ⁱ—Cd1—Cl1ⁱ	87.784 (12)
C5—C6—C7	120.93 (13)	Cl2—Cd1—Cl1ⁱ	92.218 (12)
C6—C7—N1	110.75 (10)	Cl3—Cd1—Cl1ⁱ	90.322 (15)
C6—C7—H7A	109.5	Cl3ⁱ—Cd1—Cl1ⁱ	89.680 (15)
N1—C7—H7A	109.5	Cl2ⁱ—Cd1—Cl1	92.215 (12)
C6—C7—H7B	109.5	Cl2—Cd1—Cl1	87.783 (11)
N1—C7—H7B	109.5	Cl3—Cd1—Cl1	89.678 (14)
H7A—C7—H7B	108.1	Cl3ⁱ—Cd1—Cl1	90.321 (14)
N1—C8—C9	109.69 (10)	Cl1ⁱ—Cd1—Cl1	180.0
N1—C8—H8A	109.7	C8—N1—C11	109.14 (9)
C9—C8—H8A	109.7	C8—N1—C7	113.30 (10)
N1—C8—H8B	109.7	C11—N1—C7	110.23 (9)
C9—C8—H8B	109.7	C8—N1—H1	108.9 (11)
H8A—C8—H8B	108.2	C11—N1—H1	106.7 (11)
N2—C9—C8	110.79 (9)	C7—N1—H1	108.3 (12)
N2—C9—H9A	109.5	C9—N2—C10	111.02 (9)
C8—C9—H9A	109.5	C9—N2—H2A	109.4
N2—C9—H9B	109.5	C10—N2—H2A	109.4
C8—C9—H9B	109.5	C9—N2—H2B	109.4
H9A—C9—H9B	108.1	C10—N2—H2B	109.4
N2—C10—C11	110.58 (10)	H2A—N2—H2B	108.0
N2—C10—H10A	109.5	H1A—O1—H1B	103 (3)

C6—C1—C2—C3	1.0 (2)	N1—C8—C9—N2	59.09 (13)
C1—C2—C3—C4	−1.8 (2)	N2—C10—C11—N1	−56.82 (13)
C2—C3—C4—C5	0.7 (2)	C9—C8—N1—C11	−59.78 (12)
C3—C4—C5—C6	1.1 (2)	C9—C8—N1—C7	176.99 (10)
C2—C1—C6—C5	0.8 (2)	C10—C11—N1—C8	59.02 (13)
C2—C1—C6—C7	−175.11 (13)	C10—C11—N1—C7	−175.95 (10)
C4—C5—C6—C1	−1.8 (2)	C6—C7—N1—C8	−48.38 (14)
C4—C5—C6—C7	173.99 (12)	C6—C7—N1—C11	−171.01 (10)
C1—C6—C7—N1	109.33 (14)	C8—C9—N2—C10	−56.81 (13)
C5—C6—C7—N1	−66.48 (15)	C11—C10—N2—C9	55.34 (12)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···Cl1ⁱⁱ	0.92	2.58	3.3383 (11)	140
N2—H2A···Cl2ⁱⁱ	0.92	2.59	3.2672 (11)	131
N2—H2B···Cl2ⁱⁱⁱ	0.92	2.47	3.1846 (11)	135
N2—H2B···Cl3ⁱⁱⁱ	0.92	2.58	3.2799 (12)	133
N1—H1···O1	0.89 (1)	1.92 (1)	2.7945 (16)	170 (2)
O1—H1A···Cl1	0.84 (2)	2.39 (2)	3.1678 (11)	155 (2)
O1—H1B···Cl3^iv	0.83 (2)	2.42 (2)	3.2152 (11)	161 (2)
C9—H9A···Cl3ⁱⁱⁱ	0.99	2.83	3.331 (2)	112
C9—H9B···Cl3^iv	0.99	2.85	3.659 (3)	139
C10—H10A···Cl3^iv	0.99	2.73	3.565 (2)	143
C10—H10B···Cl2ⁱⁱⁱ	0.99	2.84	3.340 (4)	112
C11—H11A···Cl1ⁱⁱⁱ	0.99	2.71	3.626 (1)	154
C11—H11B···Cl1	0.99	2.72	3.587 (1)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯Cl1ⁱ	0.92	2.58	3.3383 (11)	140
N2—H2A⋯Cl2ⁱ	0.92	2.59	3.2672 (11)	131
N2—H2B⋯Cl2ⁱⁱ	0.92	2.47	3.1846 (11)	135
N2—H2B⋯Cl3ⁱⁱ	0.92	2.58	3.2799 (12)	133
N1—H1⋯O1	0.89 (1)	1.92 (1)	2.7945 (16)	170 (2)
O1—H1A⋯Cl1	0.84 (2)	2.39 (2)	3.1678 (11)	155 (2)
O1—H1B⋯Cl3ⁱⁱⁱ	0.83 (2)	2.42 (2)	3.2152 (11)	161 (2)
C9—H9A⋯Cl3ⁱⁱ	0.99	2.83	3.331 (2)	112
C9—H9B⋯Cl3ⁱⁱⁱ	0.99	2.85	3.659 (3)	139
C10—H10A⋯Cl3ⁱⁱⁱ	0.99	2.73	3.565 (2)	143
C10—H10B⋯Cl2ⁱⁱ	0.99	2.84	3.340 (4)	112
C11—H11A⋯Cl1ⁱⁱ	0.99	2.71	3.626 (1)	154
C11—H11B⋯Cl1	0.99	2.72	3.587 (1)	146

Symmetry codes: (i) ; (ii) ; (iii) .

2 in total

1. A short history of SHELX.

Authors: George M Sheldrick
Journal: Acta Crystallogr A Date: 2007-12-21 Impact factor: 2.290

2. The first X-ray structure of a hexaamminecobalt(III) salt with two different complex chlorocadmium anions: synthesis, characterization and crystal structure of [Co(NH3)6]4[CdCl6][CdCl4(SCN)(H2O)]2Cl2.2H2O.

Authors: Ritu Bala; Raj Pal Sharma; Upendra Sharma; Valeria Ferretti
Journal: Acta Crystallogr C Date: 2006-11-30 Impact factor: 1.172

2 in total

1 in total

1. Poly[piperazine-1,4-diium [μ(4)-chlorido-μ(3)-chlorido-tri-μ(2)-chlorido-chloridodicadmate(II)] monohydrate].

Authors: Marwa Adib; Meher El Glaoui; Pedro Sidonio Pereira da Silva; Manuela Ramos Silva; Cherif Ben Nasr
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2012-01-21

1 in total