2-Amino-5-chloro-pyridinium 3-carb-oxy-4-hy-droxy-benzene-sulfonate.

The asymmetric unit of the title salt, C(5)H(6)ClN(2) (+)·C(7)H(5)O(6)S(-), contains two independent 2-amino-5-chloro-pyridinium cations and two independent 3-carb-oxy-4-hy-droxy-benzene-sulfonate anions. In both anions, the O atoms of the sulfonate group are disordered over two sets of positions, with occupancy ratios of 0.47 (5):0.53 (5) and 0.50 (8):0.50 (8). In each anion, an intra-molecular O-H⋯O hydrogen bond generating an S(6) motif is observed. In the crystal structure, the cations and anions are linked via N-H⋯O, O-H⋯O and C-H⋯O hydrogen bonds, forming a two-dimensional network parallel to (110). The structure is further stabilized by π-π inter-actions between cations and anions [centroid-centroid distance = 3.5454 (12) Å]. The crystal studied was a non-merohedral twin, with a ratio of the twin components of 0.715 (3):0.285 (3).

Related literature

For applications of inter­molecular inter­actions, see: Lam & Mak (2000 ▶). For sulfosalicylic acid complexes, see: Smith et al. (2004 ▶); Muthiah et al. (2003 ▶); Raj et al. (2003 ▶); Fan et al. (2005 ▶). For a related structure, see: Pourayoubi et al. (2007 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C5H6ClN2 +·C7H5O6S−

M = 346.74

Triclinic,

a = 7.9455 (3) Å

b = 10.9173 (5) Å

c = 16.3535 (7) Å

α = 85.223 (2)°

β = 83.327 (2)°

γ = 85.842 (2)°

V = 1401.22 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.45 mm−1

T = 296 K

0.50 × 0.36 × 0.15 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.804, T max = 0.935

8143 measured reflections

8143 independent reflections

5951 reflections with I > 2σ(I)

R int = 0.000

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.158

S = 1.04

8143 reflections

478 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.54 e Å−3

Δρmin = −0.42 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: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810032290/ci5152sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810032290/ci5152Isup2.hkl

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

C5H6ClN2+·C7H5O6S−	Z = 4
Mr = 346.74	F(000) = 712
Triclinic, P1	Dx = 1.644 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.9455 (3) Å	Cell parameters from 9907 reflections
b = 10.9173 (5) Å	θ = 2.5–29.9°
c = 16.3535 (7) Å	µ = 0.45 mm−1
α = 85.223 (2)°	T = 296 K
β = 83.327 (2)°	Plate, yellow
γ = 85.842 (2)°	0.50 × 0.36 × 0.15 mm
V = 1401.22 (10) Å3

Bruker SMART APEXII CCD area-detector diffractometer	8143 independent reflections
Radiation source: fine-focus sealed tube	5951 reflections with I > 2σ(I)
graphite	Rint = 0.000
φ and ω scans	θmax = 30.1°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→11
Tmin = 0.804, Tmax = 0.935	k = −15→15
8143 measured reflections	l = 0→22

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.158	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0866P)2 + 0.2919P] where P = (Fo2 + 2Fc2)/3
8143 reflections	(Δ/σ)max = 0.001
478 parameters	Δρmax = 0.54 e Å−3
6 restraints	Δρmin = −0.42 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	Occ. (<1)
S1A	0.35527 (7)	0.80743 (5)	0.00751 (3)	0.04328 (15)
O1A	0.7640 (2)	0.53220 (16)	0.24854 (11)	0.0476 (4)
O2A	0.5653 (2)	0.63703 (16)	0.36240 (9)	0.0513 (4)
O3A	0.3497 (2)	0.76513 (15)	0.32837 (10)	0.0455 (4)
O4A	0.460 (2)	0.837 (2)	−0.0643 (13)	0.072 (5)	0.47 (5)
O5A	0.233 (3)	0.711 (3)	−0.0064 (12)	0.086 (4)	0.47 (5)
O6A	0.266 (3)	0.906 (2)	0.0472 (9)	0.075 (4)	0.47 (5)
O4X	0.465 (2)	0.822 (2)	−0.0720 (11)	0.061 (3)	0.53 (5)
O5X	0.2139 (10)	0.7391 (10)	0.0023 (6)	0.045 (2)	0.53 (5)
O6X	0.304 (2)	0.9285 (11)	0.0377 (11)	0.074 (3)	0.53 (5)
C1A	0.4393 (2)	0.74515 (17)	0.16239 (11)	0.0312 (4)
H1AA	0.3498	0.8004	0.1792	0.037*
C2A	0.4802 (3)	0.72879 (19)	0.07962 (12)	0.0352 (4)
C3A	0.6153 (3)	0.6469 (2)	0.05434 (14)	0.0496 (6)
H3AA	0.6427	0.6358	−0.0015	0.060*
C4A	0.7087 (3)	0.5821 (2)	0.11146 (14)	0.0506 (6)
H4AA	0.7989	0.5279	0.0940	0.061*
C5A	0.6684 (2)	0.59768 (18)	0.19527 (12)	0.0352 (4)
C6A	0.5314 (2)	0.67910 (16)	0.22106 (11)	0.0291 (4)
C7A	0.4856 (2)	0.69252 (17)	0.30980 (12)	0.0327 (4)
Cl1A	0.65336 (10)	0.96478 (9)	0.40572 (4)	0.0741 (2)
N1A	0.6964 (2)	0.97630 (18)	0.16358 (12)	0.0434 (4)
N2A	0.8778 (3)	0.8864 (2)	0.06209 (13)	0.0584 (6)
H2AA	0.8203	0.9251	0.0255	0.070*
H2AB	0.9646	0.8383	0.0472	0.070*
C8A	0.8330 (3)	0.9006 (2)	0.14072 (14)	0.0415 (5)
C9A	0.9200 (3)	0.8392 (2)	0.20505 (16)	0.0469 (5)
H9AA	1.0138	0.7854	0.1922	0.056*
C10A	0.8675 (3)	0.8583 (2)	0.28486 (15)	0.0460 (5)
H10A	0.9259	0.8186	0.3266	0.055*
C11A	0.7244 (3)	0.9383 (2)	0.30458 (14)	0.0438 (5)
C12A	0.6419 (3)	0.9960 (2)	0.24326 (15)	0.0448 (5)
H12A	0.5475	1.0494	0.2557	0.054*
S1B	0.85425 (6)	0.30940 (5)	0.47122 (3)	0.03661 (13)
O1B	1.2477 (2)	0.02225 (16)	0.21626 (10)	0.0469 (4)
O2B	1.0653 (2)	0.14325 (18)	0.11015 (10)	0.0600 (5)
O3B	0.8506 (2)	0.27142 (16)	0.15525 (11)	0.0530 (4)
O4B	0.9689 (18)	0.322 (2)	0.5284 (9)	0.078 (5)	0.50 (8)
O5B	0.7188 (19)	0.226 (2)	0.5092 (10)	0.053 (3)	0.50 (8)
O6B	0.784 (2)	0.4156 (19)	0.4259 (9)	0.061 (3)	0.50 (8)
O4Y	0.9709 (15)	0.3365 (13)	0.5308 (7)	0.042 (3)	0.50 (8)
O5Y	0.7124 (15)	0.2449 (19)	0.5077 (10)	0.041 (2)	0.50 (8)
O6Y	0.802 (2)	0.4296 (15)	0.4326 (11)	0.059 (3)	0.50 (8)
C1B	0.9347 (2)	0.24440 (17)	0.31394 (12)	0.0309 (4)
H1BA	0.8522	0.3052	0.3003	0.037*
C2B	0.9681 (2)	0.22231 (17)	0.39468 (11)	0.0310 (4)
C3B	1.0904 (3)	0.13016 (19)	0.41552 (12)	0.0370 (4)
H3BA	1.1114	0.1140	0.4703	0.044*
C4B	1.1802 (3)	0.06305 (19)	0.35518 (13)	0.0390 (4)
H4BA	1.2607	0.0013	0.3695	0.047*
C5B	1.1508 (2)	0.08727 (17)	0.27276 (12)	0.0323 (4)
C6B	1.0231 (2)	0.17659 (16)	0.25225 (11)	0.0292 (4)
C7B	0.9840 (3)	0.19622 (19)	0.16594 (13)	0.0371 (4)
Cl1B	0.81241 (10)	0.51032 (8)	0.86096 (4)	0.0679 (2)
N1B	0.7949 (2)	0.52963 (17)	0.62141 (11)	0.0374 (4)
N2B	0.6228 (3)	0.6290 (2)	0.53013 (13)	0.0544 (5)
H2BA	0.6839	0.5943	0.4905	0.065*
H2BB	0.5371	0.6782	0.5199	0.065*
C8B	0.6606 (3)	0.60676 (19)	0.60619 (13)	0.0375 (4)
C9B	0.5673 (3)	0.6602 (2)	0.67497 (15)	0.0450 (5)
H9BA	0.4743	0.7149	0.6671	0.054*
C10B	0.6122 (3)	0.6323 (2)	0.75211 (14)	0.0456 (5)
H10B	0.5497	0.6669	0.7971	0.055*
C11B	0.7538 (3)	0.5506 (2)	0.76350 (13)	0.0402 (4)
C12B	0.8428 (3)	0.5010 (2)	0.69775 (14)	0.0397 (4)
H12B	0.9370	0.4471	0.7048	0.048*
H2OA	0.328 (4)	0.768 (3)	0.379 (2)	0.075 (10)*
H2OB	0.840 (4)	0.279 (3)	0.106 (2)	0.062 (9)*
H1OB	1.210 (4)	0.046 (3)	0.172 (2)	0.058 (8)*
H1OA	0.724 (4)	0.545 (3)	0.297 (2)	0.069 (9)*
H1NB	0.855 (3)	0.496 (3)	0.5796 (19)	0.055 (8)*
H1NA	0.644 (4)	1.017 (3)	0.126 (2)	0.065 (9)*

	U11	U22	U33	U12	U13	U23
S1A	0.0503 (3)	0.0502 (3)	0.0293 (3)	0.0092 (2)	−0.0148 (2)	0.0015 (2)
O1A	0.0462 (9)	0.0562 (10)	0.0372 (8)	0.0221 (7)	−0.0100 (7)	0.0004 (7)
O2A	0.0643 (10)	0.0587 (10)	0.0276 (7)	0.0213 (8)	−0.0099 (7)	0.0010 (7)
O3A	0.0515 (9)	0.0503 (9)	0.0298 (7)	0.0173 (7)	0.0029 (6)	−0.0019 (6)
O4A	0.070 (7)	0.085 (6)	0.049 (8)	0.030 (5)	0.002 (5)	0.027 (5)
O5A	0.125 (9)	0.081 (8)	0.066 (6)	−0.031 (6)	−0.071 (6)	0.024 (5)
O6A	0.088 (7)	0.093 (9)	0.037 (3)	0.063 (6)	−0.017 (4)	−0.007 (5)
O4X	0.061 (6)	0.093 (7)	0.027 (3)	−0.001 (5)	−0.007 (3)	0.011 (4)
O5X	0.044 (4)	0.055 (3)	0.036 (2)	0.002 (2)	−0.015 (3)	0.002 (2)
O6X	0.107 (7)	0.039 (3)	0.078 (7)	0.019 (4)	−0.040 (5)	−0.007 (3)
C1A	0.0317 (9)	0.0326 (9)	0.0295 (9)	0.0047 (7)	−0.0072 (7)	−0.0037 (7)
C2A	0.0392 (10)	0.0390 (10)	0.0280 (9)	0.0057 (8)	−0.0099 (7)	−0.0036 (7)
C3A	0.0586 (14)	0.0608 (14)	0.0274 (10)	0.0219 (11)	−0.0074 (9)	−0.0101 (9)
C4A	0.0527 (13)	0.0596 (14)	0.0357 (11)	0.0279 (11)	−0.0050 (9)	−0.0090 (10)
C5A	0.0363 (9)	0.0375 (10)	0.0311 (9)	0.0089 (8)	−0.0075 (7)	−0.0023 (8)
C6A	0.0302 (8)	0.0300 (9)	0.0270 (8)	0.0029 (7)	−0.0046 (6)	−0.0032 (7)
C7A	0.0385 (9)	0.0305 (9)	0.0282 (9)	0.0017 (7)	−0.0036 (7)	−0.0010 (7)
Cl1A	0.0750 (5)	0.1075 (6)	0.0413 (3)	0.0024 (4)	−0.0094 (3)	−0.0165 (4)
N1A	0.0434 (10)	0.0474 (10)	0.0375 (9)	0.0002 (8)	−0.0086 (8)	0.0109 (8)
N2A	0.0645 (13)	0.0678 (14)	0.0390 (11)	0.0034 (11)	0.0013 (9)	0.0032 (10)
C8A	0.0443 (11)	0.0414 (11)	0.0380 (11)	−0.0072 (9)	−0.0035 (9)	0.0042 (9)
C9A	0.0401 (11)	0.0455 (12)	0.0539 (13)	0.0031 (9)	−0.0080 (10)	0.0021 (10)
C10A	0.0472 (12)	0.0487 (12)	0.0435 (12)	−0.0025 (10)	−0.0173 (9)	0.0056 (10)
C11A	0.0428 (11)	0.0520 (13)	0.0375 (11)	−0.0071 (10)	−0.0071 (9)	−0.0022 (9)
C12A	0.0405 (11)	0.0436 (12)	0.0485 (12)	0.0016 (9)	−0.0036 (9)	0.0007 (10)
S1B	0.0375 (3)	0.0410 (3)	0.0302 (2)	0.00613 (19)	0.00170 (18)	−0.01102 (19)
O1B	0.0503 (9)	0.0549 (10)	0.0337 (8)	0.0255 (7)	−0.0069 (7)	−0.0143 (7)
O2B	0.0735 (12)	0.0750 (12)	0.0305 (8)	0.0284 (10)	−0.0126 (8)	−0.0174 (8)
O3B	0.0641 (11)	0.0569 (10)	0.0401 (9)	0.0240 (8)	−0.0265 (8)	−0.0124 (8)
O4B	0.051 (5)	0.115 (10)	0.076 (7)	0.002 (5)	−0.006 (4)	−0.067 (7)
O5B	0.067 (7)	0.052 (5)	0.039 (4)	−0.015 (4)	0.022 (4)	−0.018 (3)
O6B	0.079 (5)	0.057 (6)	0.043 (3)	0.041 (5)	−0.012 (5)	−0.014 (3)
O4Y	0.044 (4)	0.049 (5)	0.035 (4)	0.006 (2)	−0.009 (3)	−0.024 (3)
O5Y	0.035 (4)	0.053 (5)	0.035 (4)	0.004 (3)	−0.001 (3)	−0.007 (3)
O6Y	0.078 (5)	0.033 (3)	0.058 (6)	0.007 (4)	0.028 (5)	−0.009 (3)
C1B	0.0306 (8)	0.0294 (9)	0.0324 (9)	0.0055 (7)	−0.0051 (7)	−0.0053 (7)
C2B	0.0299 (8)	0.0334 (9)	0.0292 (9)	0.0036 (7)	−0.0006 (7)	−0.0077 (7)
C3B	0.0416 (10)	0.0429 (11)	0.0259 (9)	0.0084 (8)	−0.0077 (7)	−0.0027 (8)
C4B	0.0421 (10)	0.0386 (10)	0.0349 (10)	0.0146 (8)	−0.0082 (8)	−0.0044 (8)
C5B	0.0329 (9)	0.0323 (9)	0.0316 (9)	0.0073 (7)	−0.0044 (7)	−0.0092 (7)
C6B	0.0308 (8)	0.0293 (8)	0.0284 (8)	0.0027 (7)	−0.0069 (7)	−0.0059 (7)
C7B	0.0446 (11)	0.0368 (10)	0.0314 (9)	0.0057 (8)	−0.0117 (8)	−0.0077 (8)
Cl1B	0.0757 (5)	0.0929 (5)	0.0356 (3)	−0.0065 (4)	−0.0114 (3)	0.0010 (3)
N1B	0.0349 (8)	0.0443 (10)	0.0331 (8)	0.0013 (7)	0.0007 (7)	−0.0125 (7)
N2B	0.0505 (11)	0.0758 (15)	0.0366 (10)	0.0078 (10)	−0.0084 (8)	−0.0080 (10)
C8B	0.0354 (10)	0.0415 (11)	0.0357 (10)	−0.0041 (8)	−0.0011 (8)	−0.0070 (8)
C9B	0.0405 (11)	0.0451 (12)	0.0480 (12)	0.0086 (9)	−0.0007 (9)	−0.0113 (10)
C10B	0.0476 (12)	0.0508 (13)	0.0379 (11)	−0.0012 (10)	0.0055 (9)	−0.0166 (9)
C11B	0.0465 (11)	0.0437 (11)	0.0315 (10)	−0.0092 (9)	−0.0047 (8)	−0.0040 (8)
C12B	0.0377 (10)	0.0396 (11)	0.0421 (11)	−0.0010 (8)	−0.0048 (8)	−0.0052 (9)

S1A—O4A	1.386 (18)	S1B—O4B	1.400 (15)
S1A—O5X	1.407 (10)	S1B—O5Y	1.418 (14)
S1A—O6A	1.411 (13)	S1B—O6B	1.436 (11)
S1A—O6X	1.463 (12)	S1B—O6Y	1.462 (12)
S1A—O4X	1.481 (16)	S1B—O4Y	1.481 (13)
S1A—O5A	1.527 (17)	S1B—O5B	1.502 (17)
S1A—C2A	1.7586 (19)	S1B—C2B	1.7605 (18)
O1A—C5A	1.348 (2)	O1B—C5B	1.347 (2)
O1A—H1OA	0.84 (3)	O1B—H1OB	0.84 (3)
O2A—C7A	1.222 (2)	O2B—C7B	1.217 (3)
O3A—C7A	1.314 (2)	O3B—C7B	1.312 (2)
O3A—H2OA	0.83 (4)	O3B—H2OB	0.82 (3)
C1A—C2A	1.378 (3)	C1B—C2B	1.375 (3)
C1A—C6A	1.396 (2)	C1B—C6B	1.394 (2)
C1A—H1AA	0.93	C1B—H1BA	0.93
C2A—C3A	1.394 (3)	C2B—C3B	1.397 (3)
C3A—C4A	1.378 (3)	C3B—C4B	1.378 (3)
C3A—H3AA	0.93	C3B—H3BA	0.93
C4A—C5A	1.392 (3)	C4B—C5B	1.395 (3)
C4A—H4AA	0.93	C4B—H4BA	0.93
C5A—C6A	1.403 (2)	C5B—C6B	1.405 (2)
C6A—C7A	1.472 (3)	C6B—C7B	1.475 (3)
Cl1A—C11A	1.725 (2)	Cl1B—C11B	1.725 (2)
N1A—C8A	1.352 (3)	N1B—C8B	1.344 (3)
N1A—C12A	1.354 (3)	N1B—C12B	1.353 (3)
N1A—H1NA	0.85 (3)	N1B—H1NB	0.88 (3)
N2A—C8A	1.313 (3)	N2B—C8B	1.312 (3)
N2A—H2AA	0.86	N2B—H2BA	0.86
N2A—H2AB	0.86	N2B—H2BB	0.86
C8A—C9A	1.421 (3)	C8B—C9B	1.417 (3)
C9A—C10A	1.352 (4)	C9B—C10B	1.355 (3)
C9A—H9AA	0.93	C9B—H9BA	0.93
C10A—C11A	1.406 (3)	C10B—C11B	1.404 (3)
C10A—H10A	0.93	C10B—H10B	0.93
C11A—C12A	1.350 (3)	C11B—C12B	1.347 (3)
C12A—H12A	0.93	C12B—H12B	0.93
O4A—S1A—O5X	118.5 (11)	O4B—S1B—O5Y	111.5 (9)
O4A—S1A—O6A	116.7 (12)	O4B—S1B—O6B	120.8 (18)
O5X—S1A—O6A	96.8 (11)	O5Y—S1B—O6B	105.3 (9)
O4A—S1A—O6X	102.2 (12)	O4B—S1B—O6Y	110.8 (18)
O5X—S1A—O6X	111.5 (7)	O5Y—S1B—O6Y	111.5 (7)
O5X—S1A—O4X	112.8 (8)	O5Y—S1B—O4Y	113.8 (7)
O6A—S1A—O4X	123.8 (12)	O6B—S1B—O4Y	115.0 (14)
O6X—S1A—O4X	109.6 (9)	O6Y—S1B—O4Y	105.0 (13)
O4A—S1A—O5A	111.0 (11)	O4B—S1B—O5B	109.7 (10)
O6A—S1A—O5A	110.2 (8)	O6B—S1B—O5B	111.7 (7)
O6X—S1A—O5A	124.9 (10)	O6Y—S1B—O5B	118.3 (9)
O4X—S1A—O5A	104.3 (10)	O4Y—S1B—O5B	112.6 (8)
O4A—S1A—C2A	108.6 (9)	O4B—S1B—C2B	105.3 (8)
O5X—S1A—C2A	108.6 (5)	O5Y—S1B—C2B	109.0 (8)
O6A—S1A—C2A	106.6 (6)	O6B—S1B—C2B	104.2 (7)
O6X—S1A—C2A	106.7 (6)	O6Y—S1B—C2B	108.4 (7)
O4X—S1A—C2A	107.3 (8)	O4Y—S1B—C2B	109.0 (5)
O5A—S1A—C2A	102.7 (7)	O5B—S1B—C2B	103.3 (9)
C5A—O1A—H1OA	110 (2)	C5B—O1B—H1OB	104.2 (19)
C7A—O3A—H2OA	111 (2)	C7B—O3B—H2OB	108 (2)
C2A—C1A—C6A	120.28 (17)	C2B—C1B—C6B	120.67 (16)
C2A—C1A—H1AA	119.9	C2B—C1B—H1BA	119.7
C6A—C1A—H1AA	119.9	C6B—C1B—H1BA	119.7
C1A—C2A—C3A	119.85 (18)	C1B—C2B—C3B	119.86 (17)
C1A—C2A—S1A	119.28 (15)	C1B—C2B—S1B	119.63 (14)
C3A—C2A—S1A	120.82 (15)	C3B—C2B—S1B	120.51 (15)
C4A—C3A—C2A	120.5 (2)	C4B—C3B—C2B	120.22 (18)
C4A—C3A—H3AA	119.7	C4B—C3B—H3BA	119.9
C2A—C3A—H3AA	119.7	C2B—C3B—H3BA	119.9
C3A—C4A—C5A	120.18 (19)	C3B—C4B—C5B	120.35 (17)
C3A—C4A—H4AA	119.9	C3B—C4B—H4BA	119.8
C5A—C4A—H4AA	119.9	C5B—C4B—H4BA	119.8
O1A—C5A—C4A	117.78 (18)	O1B—C5B—C4B	117.54 (17)
O1A—C5A—C6A	122.72 (18)	O1B—C5B—C6B	123.07 (17)
C4A—C5A—C6A	119.49 (18)	C4B—C5B—C6B	119.39 (17)
C1A—C6A—C5A	119.67 (17)	C1B—C6B—C5B	119.41 (17)
C1A—C6A—C7A	120.87 (16)	C1B—C6B—C7B	121.17 (16)
C5A—C6A—C7A	119.46 (16)	C5B—C6B—C7B	119.41 (17)
O2A—C7A—O3A	122.55 (18)	O2B—C7B—O3B	123.09 (19)
O2A—C7A—C6A	122.24 (18)	O2B—C7B—C6B	122.51 (18)
O3A—C7A—C6A	115.18 (17)	O3B—C7B—C6B	114.34 (18)
C8A—N1A—C12A	123.3 (2)	C8B—N1B—C12B	123.56 (19)
C8A—N1A—H1NA	119 (2)	C8B—N1B—H1NB	118.3 (19)
C12A—N1A—H1NA	117 (2)	C12B—N1B—H1NB	118.1 (19)
C8A—N2A—H2AA	120.0	C8B—N2B—H2BA	120.0
C8A—N2A—H2AB	120.0	C8B—N2B—H2BB	120.0
H2AA—N2A—H2AB	120.0	H2BA—N2B—H2BB	120.0
N2A—C8A—N1A	119.6 (2)	N2B—C8B—N1B	119.5 (2)
N2A—C8A—C9A	123.5 (2)	N2B—C8B—C9B	123.7 (2)
N1A—C8A—C9A	116.9 (2)	N1B—C8B—C9B	116.86 (19)
C10A—C9A—C8A	120.5 (2)	C10B—C9B—C8B	120.7 (2)
C10A—C9A—H9AA	119.8	C10B—C9B—H9BA	119.7
C8A—C9A—H9AA	119.8	C8B—C9B—H9BA	119.7
C9A—C10A—C11A	119.9 (2)	C9B—C10B—C11B	119.4 (2)
C9A—C10A—H10A	120.1	C9B—C10B—H10B	120.3
C11A—C10A—H10A	120.1	C11B—C10B—H10B	120.3
C12A—C11A—C10A	119.4 (2)	C12B—C11B—C10B	119.6 (2)
C12A—C11A—Cl1A	119.39 (19)	C12B—C11B—Cl1B	119.53 (18)
C10A—C11A—Cl1A	121.21 (18)	C10B—C11B—Cl1B	120.81 (17)
C11A—C12A—N1A	120.1 (2)	C11B—C12B—N1B	119.9 (2)
C11A—C12A—H12A	120.0	C11B—C12B—H12B	120.1
N1A—C12A—H12A	120.0	N1B—C12B—H12B	120.1
C6A—C1A—C2A—C3A	−0.7 (3)	C6B—C1B—C2B—C3B	−0.7 (3)
C6A—C1A—C2A—S1A	176.84 (15)	C6B—C1B—C2B—S1B	−179.98 (14)
O4A—S1A—C2A—C1A	145.7 (11)	O4B—S1B—C2B—C1B	−146.3 (9)
O5X—S1A—C2A—C1A	−84.1 (4)	O5Y—S1B—C2B—C1B	93.8 (6)
O6A—S1A—C2A—C1A	19.2 (13)	O6B—S1B—C2B—C1B	−18.2 (11)
O6X—S1A—C2A—C1A	36.2 (8)	O6Y—S1B—C2B—C1B	−27.7 (10)
O4X—S1A—C2A—C1A	153.7 (9)	O4Y—S1B—C2B—C1B	−141.4 (5)
O5A—S1A—C2A—C1A	−96.7 (12)	O5B—S1B—C2B—C1B	98.6 (7)
O4A—S1A—C2A—C3A	−36.8 (11)	O4B—S1B—C2B—C3B	34.4 (9)
O5X—S1A—C2A—C3A	93.4 (4)	O5Y—S1B—C2B—C3B	−85.4 (6)
O6A—S1A—C2A—C3A	−163.3 (13)	O6B—S1B—C2B—C3B	162.5 (11)
O6X—S1A—C2A—C3A	−146.3 (8)	O6Y—S1B—C2B—C3B	153.1 (10)
O4X—S1A—C2A—C3A	−28.8 (9)	O4Y—S1B—C2B—C3B	39.3 (5)
O5A—S1A—C2A—C3A	80.8 (12)	O5B—S1B—C2B—C3B	−80.6 (8)
C1A—C2A—C3A—C4A	−0.1 (4)	C1B—C2B—C3B—C4B	1.3 (3)
S1A—C2A—C3A—C4A	−177.6 (2)	S1B—C2B—C3B—C4B	−179.42 (17)
C2A—C3A—C4A—C5A	0.2 (4)	C2B—C3B—C4B—C5B	0.6 (3)
C3A—C4A—C5A—O1A	−179.9 (2)	C3B—C4B—C5B—O1B	177.2 (2)
C3A—C4A—C5A—C6A	0.4 (4)	C3B—C4B—C5B—C6B	−3.1 (3)
C2A—C1A—C6A—C5A	1.3 (3)	C2B—C1B—C6B—C5B	−1.8 (3)
C2A—C1A—C6A—C7A	−177.93 (18)	C2B—C1B—C6B—C7B	177.69 (18)
O1A—C5A—C6A—C1A	179.19 (19)	O1B—C5B—C6B—C1B	−176.61 (18)
C4A—C5A—C6A—C1A	−1.2 (3)	C4B—C5B—C6B—C1B	3.7 (3)
O1A—C5A—C6A—C7A	−1.6 (3)	O1B—C5B—C6B—C7B	3.9 (3)
C4A—C5A—C6A—C7A	178.1 (2)	C4B—C5B—C6B—C7B	−175.82 (19)
C1A—C6A—C7A—O2A	−179.1 (2)	C1B—C6B—C7B—O2B	175.9 (2)
C5A—C6A—C7A—O2A	1.7 (3)	C5B—C6B—C7B—O2B	−4.7 (3)
C1A—C6A—C7A—O3A	3.1 (3)	C1B—C6B—C7B—O3B	−6.8 (3)
C5A—C6A—C7A—O3A	−176.13 (18)	C5B—C6B—C7B—O3B	172.69 (18)
C12A—N1A—C8A—N2A	−180.0 (2)	C12B—N1B—C8B—N2B	−179.7 (2)
C12A—N1A—C8A—C9A	0.6 (3)	C12B—N1B—C8B—C9B	0.5 (3)
N2A—C8A—C9A—C10A	179.8 (2)	N2B—C8B—C9B—C10B	179.4 (2)
N1A—C8A—C9A—C10A	−0.8 (3)	N1B—C8B—C9B—C10B	−0.8 (3)
C8A—C9A—C10A—C11A	0.8 (4)	C8B—C9B—C10B—C11B	0.7 (4)
C9A—C10A—C11A—C12A	−0.6 (3)	C9B—C10B—C11B—C12B	−0.1 (3)
C9A—C10A—C11A—Cl1A	179.90 (19)	C9B—C10B—C11B—Cl1B	−178.64 (18)
C10A—C11A—C12A—N1A	0.3 (3)	C10B—C11B—C12B—N1B	−0.3 (3)
Cl1A—C11A—C12A—N1A	179.87 (17)	Cl1B—C11B—C12B—N1B	178.26 (16)
C8A—N1A—C12A—C11A	−0.4 (4)	C8B—N1B—C12B—C11B	0.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2A—H2AA···O6Xi	0.86	2.08	2.900 (15)	159
N2A—H2AB···O5Xii	0.86	2.26	3.115 (9)	171
N2B—H2BA···O6B	0.86	2.34	3.114 (19)	150
N2B—H2BA···O6Y	0.86	2.20	2.985 (17)	152
N2B—H2BB···O5Biii	0.86	2.30	3.146 (17)	168
N2B—H2BB···O5Yiii	0.86	2.18	3.013 (15)	164
O3A—H2OA···O5Biii	0.83 (3)	1.83 (4)	2.657 (16)	180 (5)
O3A—H2OA···O5Yiii	0.83 (3)	1.84 (4)	2.663 (16)	173 (3)
O3B—H2OB···O5Xiv	0.82 (3)	1.90 (3)	2.698 (10)	166 (3)
O1B—H1OB···O2B	0.83 (3)	1.84 (3)	2.604 (2)	152 (3)
O1A—H1OA···O2A	0.84 (3)	1.85 (3)	2.584 (2)	145 (3)
O1A—H1OA···O6B	0.84 (3)	2.51 (4)	3.086 (16)	127 (3)
O1A—H1OA···O6Y	0.84 (3)	2.58 (4)	3.163 (18)	128 (3)
N1B—H1NB···O4B	0.88 (3)	2.23 (4)	2.999 (19)	146 (3)
N1B—H1NB···O4Y	0.88 (3)	2.09 (3)	2.865 (13)	148 (3)
N1A—H1NA···O4Xi	0.86 (3)	2.08 (4)	2.87 (2)	153 (3)
C1A—H1AA···O1Bv	0.93	2.60	3.422 (3)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2A—H2AA⋯O6Xi	0.86	2.08	2.900 (15)	159
N2A—H2AB⋯O5Xii	0.86	2.26	3.115 (9)	171
N2B—H2BA⋯O6B	0.86	2.34	3.114 (19)	150
N2B—H2BA⋯O6Y	0.86	2.20	2.985 (17)	152
N2B—H2BB⋯O5Biii	0.86	2.30	3.146 (17)	168
N2B—H2BB⋯O5Yiii	0.86	2.18	3.013 (15)	164
O3A—H2OA⋯O5Biii	0.83 (3)	1.83 (4)	2.657 (16)	180 (5)
O3A—H2OA⋯O5Yiii	0.83 (3)	1.84 (4)	2.663 (16)	173 (3)
O3B—H2OB⋯O5Xiv	0.82 (3)	1.90 (3)	2.698 (10)	166 (3)
O1B—H1OB⋯O2B	0.83 (3)	1.84 (3)	2.604 (2)	152 (3)
O1A—H1OA⋯O2A	0.84 (3)	1.85 (3)	2.584 (2)	145 (3)
O1A—H1OO⋯O6B	0.84 (3)	2.51 (4)	3.086 (16)	127 (3)
O1A—H1OA⋯O6Y	0.84 (3)	2.58 (4)	3.163 (18)	128 (3)
N1B—H1NB⋯O4B	0.88 (3)	2.23 (4)	2.999 (19)	146 (3)
N1B—H1NB⋯O4Y	0.88 (3)	2.09 (3)	2.865 (13)	148 (3)
N1A—H1NA⋯O4Xi	0.86 (3)	2.08 (4)	2.87 (2)	153 (3)
C1A—H1AA⋯O1Bv	0.93	2.60	3.422 (3)	148

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