Tetra-kis(2-amino-6-methyl-pyridinium) hexa-chloridobismuthate(III) chloride monohydrate.

The asymmetric unit of the title compound, (C(6)H(9)N(2))(4)[BiCl(6)]Cl·H(2)O, contains four protonated 2-amino-6-methyl-pyridine (HAMP) cations and two-halves of two [BiCl(6)](3-) anions, together with one water mol-ecule and one chloride anion. The Bi(III) atoms are hexa-coordinated by Cl atoms, forming distorted octa-hedral geometries. In the crystal structure, intra-molecular O-H⋯Cl and N-H⋯Cl, and inter-molecular O-H⋯Cl and N-H⋯O inter-actions link the mol-ecules into a three-dimensional network.

Related literature

For related structures, see: Albrecht et al. (2003 ▶); Feng et al. (2007 ▶); Inuzuka & Fujimoto (1986 ▶, 1990 ▶); Ishikawa et al. (2002 ▶); Jin et al. (2000 ▶, 2001 ▶, 2005 ▶); Luque et al. (1997 ▶); Nahringbauer & Kvick (1977 ▶); Ren et al. (2002 ▶); Rivas et al. (2003 ▶); Salwa et al. (2008 ▶); Xu et al. (2006 ▶).

Experimental

Crystal data

(C6H9N2)4[BiCl6]Cl·H2O

M = 911.75

Triclinic,

a = 10.3345 (7) Å

b = 10.7605 (7) Å

c = 17.2673 (11) Å

α = 100.3370 (10)°

β = 103.7370 (10)°

γ = 99.2280 (10)°

V = 1793.1 (2) Å3

Z = 2

Mo Kα radiation

μ = 5.47 mm−1

T = 273 K

0.42 × 0.31 × 0.25 mm

Data collection

Bruker SMART APEX area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.153, T max = 0.185 (expected range = 0.211–0.255)

9489 measured reflections

6240 independent reflections

5171 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.070

S = 1.07

6240 reflections

373 parameters

3 restraints

H-atom parameters constrained

Δρmax = 0.55 e Å−3

Δρmin = −1.13 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809025446/hk2720sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809025446/hk2720Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

(C6H9N2)4[BiCl6]Cl·H2O	Z = 2
Mr = 911.75	F(000) = 896.0
Triclinic, P1	Dx = 1.689 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.3345 (7) Å	Cell parameters from 3117 reflections
b = 10.7605 (7) Å	θ = 2.2–25.1°
c = 17.2673 (11) Å	µ = 5.47 mm−1
α = 100.337 (1)°	T = 273 K
β = 103.737 (1)°	Block, colorless
γ = 99.228 (1)°	0.42 × 0.31 × 0.25 mm
V = 1793.1 (2) Å3

Bruker SMART APEX area-detector diffractometer	6240 independent reflections
Radiation source: fine-focus sealed tube	5171 reflections with I > 2σ(I)
graphite	Rint = 0.016
φ and ω scans	θmax = 25.0°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −10→12
Tmin = 0.153, Tmax = 0.185	k = −9→12
9489 measured reflections	l = −20→20

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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.070	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0359P)2 + 0.5382P] where P = (Fo2 + 2Fc2)/3
6240 reflections	(Δ/σ)max < 0.001
373 parameters	Δρmax = 0.55 e Å−3
3 restraints	Δρmin = −1.13 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	Uiso*/Ueq
Bi1	0.5000	0.5000	0.5000	0.03208 (7)
Bi2	0.5000	0.5000	0.0000	0.03407 (7)
Cl1	0.76385 (11)	0.55587 (11)	0.49688 (6)	0.0503 (3)
Cl2	0.46967 (13)	0.73844 (10)	0.48394 (7)	0.0537 (3)
Cl3	0.42723 (11)	0.42048 (10)	0.33422 (6)	0.0489 (3)
Cl4	0.56519 (12)	0.32481 (10)	0.08902 (7)	0.0573 (3)
Cl5	0.33494 (12)	0.56458 (11)	0.09478 (7)	0.0547 (3)
Cl6	0.70316 (12)	0.68084 (10)	0.10950 (7)	0.0599 (3)
Cl7	0.88297 (16)	0.15531 (15)	0.23702 (9)	0.0826 (4)
O1	1.1851 (4)	0.1659 (3)	0.3096 (2)	0.0857 (11)
H1WB	1.1129	0.1812	0.2849	0.103*
H1WA	1.2497	0.2292	0.3265	0.103*
N1	0.1776 (4)	0.0607 (4)	0.1493 (3)	0.0592 (11)
H1	0.1767	0.0927	0.1985	0.071*
N2	0.2421 (5)	0.2693 (4)	0.1378 (3)	0.0810 (13)
H2A	0.2425	0.2963	0.1878	0.097*
H2B	0.2629	0.3238	0.1095	0.097*
N3	0.5100 (4)	0.8575 (3)	0.20673 (19)	0.0474 (9)
H3A	0.5145	0.7911	0.1722	0.057*
N4	0.4851 (5)	0.7216 (4)	0.2933 (2)	0.0781 (14)
H4A	0.4900	0.6588	0.2563	0.094*
H4B	0.4747	0.7079	0.3392	0.094*
N5	0.8447 (4)	0.0458 (4)	0.3837 (3)	0.0502 (9)
H5	0.8607	0.0669	0.3407	0.060*
N6	0.8249 (5)	0.2543 (4)	0.4248 (3)	0.0840 (14)
H6D	0.8403	0.2684	0.3800	0.101*
H6E	0.8112	0.3155	0.4593	0.101*
N7	0.8615 (3)	0.4698 (3)	0.2053 (2)	0.0421 (8)
H7	0.7861	0.4446	0.1672	0.050*
N8	0.7323 (4)	0.4673 (4)	0.2964 (2)	0.0664 (11)
H8A	0.6604	0.4426	0.2556	0.080*
H8B	0.7251	0.4784	0.3456	0.080*
C1	0.2094 (5)	0.1432 (6)	0.1040 (3)	0.0618 (13)
C2	0.2063 (7)	0.0900 (8)	0.0237 (4)	0.094 (2)
H2	0.2286	0.1435	−0.0100	0.112*
C3	0.1711 (9)	−0.0385 (10)	−0.0048 (5)	0.124 (3)
H3	0.1641	−0.0735	−0.0593	0.149*
C4	0.1446 (9)	−0.1207 (8)	0.0466 (6)	0.130 (3)
H4	0.1259	−0.2099	0.0274	0.156*
C5	0.1466 (6)	−0.0699 (6)	0.1232 (4)	0.0808 (17)
C6	0.1129 (8)	−0.1460 (6)	0.1820 (5)	0.126 (3)
H6A	0.1219	−0.0885	0.2333	0.189*
H6B	0.1741	−0.2038	0.1902	0.189*
H6C	0.0209	−0.1951	0.1606	0.189*
C7	0.4938 (5)	0.8408 (4)	0.2794 (2)	0.0474 (10)
C8	0.4871 (5)	0.9476 (5)	0.3355 (3)	0.0513 (11)
H8	0.4766	0.9398	0.3866	0.062*
C9	0.4962 (5)	1.0642 (5)	0.3144 (3)	0.0547 (12)
H9	0.4914	1.1366	0.3513	0.066*
C10	0.5125 (5)	1.0763 (4)	0.2382 (3)	0.0510 (11)
H10	0.5185	1.1565	0.2247	0.061*
C11	0.5198 (5)	0.9730 (4)	0.1841 (3)	0.0452 (10)
C12	0.5398 (6)	0.9723 (5)	0.1016 (3)	0.0676 (14)
H12A	0.5410	0.8862	0.0753	0.101*
H12B	0.6248	1.0290	0.1069	0.101*
H12C	0.4665	1.0014	0.0692	0.101*
C13	0.8223 (5)	0.1368 (5)	0.4407 (3)	0.0536 (12)
C14	0.7972 (6)	0.1029 (6)	0.5099 (3)	0.0726 (16)
H14	0.7820	0.1638	0.5504	0.087*
C15	0.7949 (6)	−0.0189 (8)	0.5181 (4)	0.086 (2)
H15	0.7779	−0.0417	0.5647	0.103*
C16	0.8170 (6)	−0.1111 (6)	0.4591 (5)	0.084 (2)
H16	0.8141	−0.1954	0.4655	0.101*
C17	0.8431 (5)	−0.0771 (5)	0.3914 (4)	0.0673 (15)
C18	0.8685 (7)	−0.1648 (6)	0.3227 (4)	0.110 (3)
H18A	0.8842	−0.1179	0.2823	0.166*
H18B	0.7906	−0.2347	0.2984	0.166*
H18C	0.9471	−0.1988	0.3427	0.166*
C19	0.8552 (4)	0.4883 (4)	0.2832 (2)	0.0434 (10)
C20	0.9768 (5)	0.5280 (4)	0.3444 (3)	0.0513 (11)
H20	0.9765	0.5424	0.3991	0.062*
C21	1.0970 (5)	0.5458 (5)	0.3242 (3)	0.0513 (11)
H21	1.1790	0.5707	0.3653	0.062*
C22	1.0979 (5)	0.5268 (4)	0.2419 (3)	0.0482 (11)
H22	1.1800	0.5408	0.2282	0.058*
C23	0.9793 (4)	0.4882 (4)	0.1830 (3)	0.0428 (10)
C24	0.9655 (5)	0.4629 (6)	0.0929 (3)	0.0738 (15)
H24A	0.8707	0.4364	0.0633	0.111*
H24B	1.0121	0.3957	0.0783	0.111*
H24C	1.0048	0.5403	0.0793	0.111*

	U11	U22	U33	U12	U13	U23
Bi1	0.03694 (12)	0.03611 (12)	0.02651 (11)	0.00931 (9)	0.01195 (8)	0.00979 (8)
Bi2	0.03917 (13)	0.03067 (12)	0.02879 (11)	0.00442 (9)	0.00502 (9)	0.00606 (8)
Cl1	0.0429 (6)	0.0620 (7)	0.0507 (6)	0.0078 (5)	0.0165 (5)	0.0224 (5)
Cl2	0.0791 (8)	0.0442 (6)	0.0486 (6)	0.0211 (5)	0.0280 (6)	0.0170 (5)
Cl3	0.0524 (6)	0.0586 (7)	0.0340 (5)	0.0077 (5)	0.0125 (5)	0.0090 (4)
Cl4	0.0568 (7)	0.0446 (6)	0.0610 (7)	0.0003 (5)	−0.0039 (5)	0.0237 (5)
Cl5	0.0553 (7)	0.0571 (7)	0.0534 (6)	0.0082 (5)	0.0265 (5)	0.0047 (5)
Cl6	0.0538 (7)	0.0436 (6)	0.0631 (7)	0.0017 (5)	−0.0073 (5)	0.0026 (5)
Cl7	0.0804 (10)	0.0984 (11)	0.0720 (9)	0.0159 (8)	0.0196 (8)	0.0314 (8)
O1	0.075 (3)	0.089 (3)	0.078 (2)	−0.007 (2)	0.016 (2)	0.009 (2)
N1	0.054 (2)	0.054 (3)	0.070 (3)	0.0043 (19)	0.021 (2)	0.014 (2)
N2	0.101 (4)	0.066 (3)	0.091 (3)	0.015 (3)	0.046 (3)	0.033 (3)
N3	0.077 (3)	0.0354 (19)	0.0299 (17)	0.0145 (18)	0.0157 (17)	0.0055 (14)
N4	0.133 (4)	0.054 (3)	0.047 (2)	0.009 (3)	0.024 (2)	0.022 (2)
N5	0.050 (2)	0.041 (2)	0.058 (2)	0.0123 (17)	0.0093 (19)	0.0108 (18)
N6	0.113 (4)	0.050 (3)	0.098 (4)	0.029 (3)	0.040 (3)	0.015 (2)
N7	0.0369 (19)	0.053 (2)	0.0365 (18)	0.0087 (16)	0.0089 (15)	0.0119 (16)
N8	0.052 (2)	0.096 (3)	0.058 (2)	0.011 (2)	0.027 (2)	0.021 (2)
C1	0.047 (3)	0.073 (4)	0.071 (3)	0.008 (2)	0.025 (3)	0.021 (3)
C2	0.082 (5)	0.130 (7)	0.071 (4)	0.004 (4)	0.037 (4)	0.023 (4)
C3	0.112 (6)	0.144 (8)	0.083 (5)	−0.019 (6)	0.043 (5)	−0.037 (5)
C4	0.146 (8)	0.089 (6)	0.125 (7)	−0.025 (5)	0.059 (6)	−0.035 (5)
C5	0.072 (4)	0.059 (4)	0.101 (5)	−0.003 (3)	0.021 (3)	0.013 (3)
C6	0.143 (7)	0.078 (5)	0.148 (7)	−0.016 (4)	0.036 (6)	0.046 (5)
C7	0.056 (3)	0.047 (3)	0.039 (2)	0.006 (2)	0.013 (2)	0.0141 (19)
C8	0.056 (3)	0.067 (3)	0.031 (2)	0.013 (2)	0.015 (2)	0.007 (2)
C9	0.057 (3)	0.051 (3)	0.052 (3)	0.020 (2)	0.015 (2)	−0.004 (2)
C10	0.065 (3)	0.040 (3)	0.048 (3)	0.015 (2)	0.013 (2)	0.008 (2)
C11	0.052 (3)	0.041 (2)	0.045 (2)	0.012 (2)	0.014 (2)	0.014 (2)
C12	0.106 (4)	0.063 (3)	0.047 (3)	0.025 (3)	0.035 (3)	0.023 (2)
C13	0.048 (3)	0.048 (3)	0.059 (3)	0.011 (2)	0.008 (2)	0.006 (2)
C14	0.058 (3)	0.099 (5)	0.059 (3)	0.018 (3)	0.014 (3)	0.015 (3)
C15	0.060 (4)	0.117 (6)	0.086 (5)	0.010 (4)	0.013 (3)	0.056 (4)
C16	0.062 (4)	0.055 (4)	0.132 (6)	0.007 (3)	0.006 (4)	0.047 (4)
C17	0.055 (3)	0.043 (3)	0.097 (4)	0.008 (2)	0.009 (3)	0.016 (3)
C18	0.131 (6)	0.067 (4)	0.119 (5)	0.042 (4)	0.024 (5)	−0.020 (4)
C19	0.046 (2)	0.046 (2)	0.044 (2)	0.0137 (19)	0.017 (2)	0.0166 (19)
C20	0.056 (3)	0.062 (3)	0.035 (2)	0.012 (2)	0.008 (2)	0.015 (2)
C21	0.042 (3)	0.062 (3)	0.047 (3)	0.011 (2)	0.003 (2)	0.019 (2)
C22	0.039 (2)	0.062 (3)	0.047 (3)	0.014 (2)	0.014 (2)	0.016 (2)
C23	0.041 (2)	0.051 (3)	0.042 (2)	0.0134 (19)	0.0153 (19)	0.0137 (19)
C24	0.064 (3)	0.112 (5)	0.040 (3)	0.009 (3)	0.017 (2)	0.009 (3)

Bi1—Cl1i	2.7121 (11)	C3—C4	1.401 (12)
Bi1—Cl1	2.7121 (11)	C3—H3	0.9300
Bi1—Cl2	2.6888 (10)	C4—C5	1.331 (10)
Bi1—Cl2i	2.6888 (10)	C4—H4	0.9300
Bi1—Cl3i	2.7175 (10)	C5—C6	1.484 (9)
Bi1—Cl3	2.7175 (10)	C6—H6A	0.9600
Bi2—Cl4	2.7066 (10)	C6—H6B	0.9600
Bi2—Cl5	2.7146 (10)	C6—H6C	0.9600
Bi2—Cl5ii	2.7146 (10)	C7—C8	1.386 (6)
Bi2—Cl6ii	2.6932 (10)	C8—C9	1.364 (7)
Bi2—Cl6	2.6932 (11)	C8—H8	0.9300
Bi2—Cl4ii	2.7066 (10)	C9—C10	1.390 (7)
O1—H1WA	0.8278	C9—H9	0.9300
O1—H1WB	0.8249	C10—C11	1.342 (6)
N1—C1	1.336 (6)	C10—H10	0.9300
N1—C5	1.357 (7)	C11—C12	1.487 (6)
N1—H1	0.8600	C12—H12A	0.9600
N2—C1	1.331 (6)	C12—H12B	0.9600
N2—H2A	0.8600	C12—H12C	0.9600
N2—H2B	0.8600	C13—C14	1.379 (8)
N3—C7	1.344 (5)	C14—C15	1.340 (9)
N3—C11	1.363 (5)	C14—H14	0.9300
N3—H3A	0.8600	C15—C16	1.376 (10)
N4—C7	1.340 (5)	C15—H15	0.9300
N4—H4A	0.8600	C16—C17	1.358 (9)
N4—H4B	0.8600	C16—H16	0.9300
N5—C13	1.348 (6)	C17—C18	1.481 (8)
N5—C17	1.350 (6)	C18—H18A	0.9600
N5—H5	0.8600	C18—H18B	0.9600
N6—C13	1.338 (6)	C18—H18C	0.9600
N6—H6D	0.8600	C19—C20	1.384 (6)
N6—H6E	0.8600	C20—C21	1.362 (7)
N7—C19	1.341 (5)	C20—H20	0.9300
N7—C23	1.358 (5)	C21—C22	1.402 (6)
N7—H7	0.8600	C21—H21	0.9300
N8—C19	1.334 (5)	C22—C23	1.342 (6)
N8—H8A	0.8600	C22—H22	0.9300
N8—H8B	0.8600	C23—C24	1.498 (6)
C1—C2	1.392 (8)	C24—H24A	0.9600
C2—C3	1.340 (11)	C24—H24B	0.9600
C2—H2	0.9300	C24—H24C	0.9600
Cl2—Bi1—Cl2i	180.0	C5—C6—H6A	109.5
Cl2—Bi1—Cl1i	88.75 (3)	C5—C6—H6B	109.5
Cl2i—Bi1—Cl1i	91.25 (3)	H6A—C6—H6B	109.5
Cl2—Bi1—Cl1	91.25 (3)	C5—C6—H6C	109.5
Cl2i—Bi1—Cl1	88.75 (3)	H6A—C6—H6C	109.5
Cl1i—Bi1—Cl1	180.0	H6B—C6—H6C	109.5
Cl2—Bi1—Cl3i	90.89 (3)	N4—C7—N3	117.9 (4)
Cl2i—Bi1—Cl3i	89.11 (3)	N4—C7—C8	123.9 (4)
Cl1i—Bi1—Cl3i	88.60 (3)	N3—C7—C8	118.2 (4)
Cl1—Bi1—Cl3i	91.40 (3)	C9—C8—C7	118.7 (4)
Cl2—Bi1—Cl3	89.11 (3)	C9—C8—H8	120.6
Cl2i—Bi1—Cl3	90.89 (3)	C7—C8—H8	120.6
Cl1i—Bi1—Cl3	91.40 (3)	C8—C9—C10	120.8 (4)
Cl1—Bi1—Cl3	88.60 (3)	C8—C9—H9	119.6
Cl3i—Bi1—Cl3	180.0	C10—C9—H9	119.6
Cl6ii—Bi2—Cl6	180.00 (5)	C11—C10—C9	120.5 (4)
Cl6ii—Bi2—Cl4ii	89.13 (3)	C11—C10—H10	119.8
Cl6—Bi2—Cl4ii	90.87 (3)	C9—C10—H10	119.8
Cl6ii—Bi2—Cl4	90.87 (3)	C10—C11—N3	117.5 (4)
Cl6—Bi2—Cl4	89.13 (3)	C10—C11—C12	126.2 (4)
Cl4ii—Bi2—Cl4	180.00 (3)	N3—C11—C12	116.3 (4)
Cl6ii—Bi2—Cl5	92.40 (4)	C11—C12—H12A	109.5
Cl6—Bi2—Cl5	87.60 (4)	C11—C12—H12B	109.5
Cl4ii—Bi2—Cl5	91.47 (4)	H12A—C12—H12B	109.5
Cl4—Bi2—Cl5	88.53 (4)	C11—C12—H12C	109.5
Cl6ii—Bi2—Cl5ii	87.60 (4)	H12A—C12—H12C	109.5
Cl6—Bi2—Cl5ii	92.40 (4)	H12B—C12—H12C	109.5
Cl4ii—Bi2—Cl5ii	88.53 (4)	N6—C13—N5	116.6 (5)
Cl4—Bi2—Cl5ii	91.47 (4)	N6—C13—C14	125.0 (5)
Cl5—Bi2—Cl5ii	180.00 (3)	N5—C13—C14	118.5 (5)
H1WB—O1—H1WA	114.5	C15—C14—C13	119.2 (6)
C1—N1—C5	124.6 (5)	C15—C14—H14	120.4
C1—N1—H1	117.7	C13—C14—H14	120.4
C5—N1—H1	117.7	C14—C15—C16	121.6 (6)
C1—N2—H2A	120.0	C14—C15—H15	119.2
C1—N2—H2B	120.0	C16—C15—H15	119.2
H2A—N2—H2B	120.0	C17—C16—C15	119.0 (6)
C7—N3—C11	124.3 (4)	C17—C16—H16	120.5
C7—N3—H3A	117.9	C15—C16—H16	120.5
C11—N3—H3A	117.9	N5—C17—C16	118.8 (6)
C7—N4—H4A	120.0	N5—C17—C18	115.7 (6)
C7—N4—H4B	120.0	C16—C17—C18	125.4 (6)
H4A—N4—H4B	120.0	C17—C18—H18A	109.5
C13—N5—C17	122.8 (5)	C17—C18—H18B	109.5
C13—N5—H5	118.6	H18A—C18—H18B	109.5
C17—N5—H5	118.6	C17—C18—H18C	109.5
C13—N6—H6D	120.0	H18A—C18—H18C	109.5
C13—N6—H6E	120.0	H18B—C18—H18C	109.5
H6D—N6—H6E	120.0	N8—C19—N7	117.9 (4)
C19—N7—C23	124.2 (4)	N8—C19—C20	124.4 (4)
C19—N7—H7	117.9	N7—C19—C20	117.7 (4)
C23—N7—H7	117.9	C21—C20—C19	119.7 (4)
C19—N8—H8A	120.0	C21—C20—H20	120.1
C19—N8—H8B	120.0	C19—C20—H20	120.1
H8A—N8—H8B	120.0	C20—C21—C22	120.3 (4)
N2—C1—N1	118.7 (5)	C20—C21—H21	119.8
N2—C1—C2	124.3 (6)	C22—C21—H21	119.8
N1—C1—C2	117.0 (6)	C23—C22—C21	119.5 (4)
C3—C2—C1	119.8 (7)	C23—C22—H22	120.3
C3—C2—H2	120.1	C21—C22—H22	120.3
C1—C2—H2	120.1	C22—C23—N7	118.6 (4)
C2—C3—C4	120.8 (7)	C22—C23—C24	125.0 (4)
C2—C3—H3	119.6	N7—C23—C24	116.3 (4)
C4—C3—H3	119.6	C23—C24—H24A	109.5
C5—C4—C3	119.4 (7)	C23—C24—H24B	109.5
C5—C4—H4	120.3	H24A—C24—H24B	109.5
C3—C4—H4	120.3	C23—C24—H24C	109.5
C4—C5—N1	118.3 (7)	H24A—C24—H24C	109.5
C4—C5—C6	124.6 (7)	H24B—C24—H24C	109.5
N1—C5—C6	117.0 (6)
C5—N1—C1—N2	−177.8 (5)	C17—N5—C13—N6	−179.1 (5)
C5—N1—C1—C2	1.9 (8)	C17—N5—C13—C14	0.3 (7)
N2—C1—C2—C3	−179.6 (7)	N6—C13—C14—C15	178.8 (5)
N1—C1—C2—C3	0.7 (10)	N5—C13—C14—C15	−0.5 (8)
C1—C2—C3—C4	−3.6 (13)	C13—C14—C15—C16	0.0 (9)
C2—C3—C4—C5	4.1 (14)	C14—C15—C16—C17	0.7 (10)
C3—C4—C5—N1	−1.6 (12)	C13—N5—C17—C16	0.4 (8)
C3—C4—C5—C6	176.5 (8)	C13—N5—C17—C18	179.4 (5)
C1—N1—C5—C4	−1.4 (10)	C15—C16—C17—N5	−0.9 (9)
C1—N1—C5—C6	−179.6 (6)	C15—C16—C17—C18	−179.8 (6)
C11—N3—C7—N4	179.8 (4)	C23—N7—C19—N8	179.6 (4)
C11—N3—C7—C8	−0.3 (7)	C23—N7—C19—C20	−0.4 (6)
N4—C7—C8—C9	−179.6 (5)	N8—C19—C20—C21	179.5 (4)
N3—C7—C8—C9	0.5 (7)	N7—C19—C20—C21	−0.4 (7)
C7—C8—C9—C10	−0.3 (7)	C19—C20—C21—C22	1.3 (7)
C8—C9—C10—C11	0.0 (7)	C20—C21—C22—C23	−1.4 (7)
C9—C10—C11—N3	0.2 (6)	C21—C22—C23—N7	0.5 (6)
C9—C10—C11—C12	−178.7 (5)	C21—C22—C23—C24	−179.3 (5)
C7—N3—C11—C10	0.0 (7)	C19—N7—C23—C22	0.4 (6)
C7—N3—C11—C12	179.0 (4)	C19—N7—C23—C24	−179.8 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1WB···Cl7	0.83	2.28	3.051 (3)	157
N2—H2B···Cl5	0.86	2.65	3.432 (3)	151
N4—H4B···Cl2	0.86	2.48	3.307 (3)	163
N5—H5···Cl7	0.86	2.21	3.059 (3)	168
N7—H7···Cl4	0.86	2.38	3.204 (3)	161
N8—H8B···Cl1	0.86	2.51	3.343 (3)	164
O1—H1WA···Cl3iii	0.83	2.49	3.290 (3)	163
N1—H1···O1iv	0.86	1.91	2.774 (3)	177

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1WB⋯Cl7	0.825	2.28	3.051 (3)	157
N2—H2B⋯Cl5	0.86	2.65	3.432 (3)	151
N4—H4B⋯Cl2	0.86	2.48	3.307 (3)	163
N5—H5⋯Cl7	0.86	2.21	3.059 (3)	168
N7—H7⋯Cl4	0.86	2.38	3.204 (3)	161
N8—H8B⋯Cl1	0.86	2.51	3.343 (3)	164
O1—H1WA⋯Cl3i	0.828	2.49	3.290 (3)	163
N1—H1⋯O1ii	0.86	1.91	2.774 (3)	177

Symmetry codes: (i) ; (ii) .