Amlodipine mesylate monohydrate: a twinned and disordered structure

In the title compound, (R,S)-3-ethyl 5-methyl 2-(2-ammonio­ethoxy­meth­yl)4-(2-chloro­phen­yl)-6-methyl-1,4-dihydro­pyridine-3,5-dicarboxyl­ate methane­sulfonate monohydrate, C₂₀H₂₆ClN₂O₅⁺·CH₃O₃S^-·H₂O, the cation, anion and water mol­ecule are linked by extensive hydrogen bonding which results in the formation of ribbons in the c direction.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.003 Å
• Disorder in main residue
• R factor = 0.048
• wR factor = 0.128
• Data-to-parameter ratio = 34.0

checkCIF/PLATON results

No syntax errors found



Alert level A
REFLT03_ALERT_3_A  Reflection count > 15% excess reflns - sys abs data present?
           From the CIF: _diffrn_reflns_theta_max           26.69
           From the CIF: _diffrn_reflns_theta_full          26.69
           From the CIF: _reflns_number_total              10949
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         5424
           Completeness (_total/calc)            201.86%
PLAT021_ALERT_1_A Ratio Unique / Expected Reflections too High ...       2.02

Alert level B
PLAT201_ALERT_2_B Isotropic non-H Atoms in Main Residue(s) .......          1

Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.802     1.000
            Tmin(prime) and Tmax expected:      0.857     0.956
            RR(prime) =      0.894
            Please check that your absorption correction is appropriate.
PLAT030_ALERT_1_C _diffrn_reflns_number .LE.  _reflns_number_total          ?
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.89
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.96
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C51
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for          S
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.11
PLAT301_ALERT_3_C Main Residue  Disorder .........................       7.00 Perc.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          5
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C H3 O3 S

   2 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
  10 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: APEX2 (Bruker, 2006); cell refinement: CELL-NOW (Sheldrick, 2003); data reduction: APEX2; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2003); software used to prepare material for publication: SHELXTL.

(R,S)-3-ethyl 5-methyl 2-(2-ammonioethoxymethyl)4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine- 3,5-dicarboxylate methanesulfonate hydrate

Crystal data

C20H26ClN2O5^+·CH3O3S^−·H2O	F(000) = 2208
Mr = 522.99	Dx = 1.356 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5895 reflections
a = 47.656 (11) Å	θ = 2.6–24.6°
b = 11.069 (2) Å	µ = 0.28 mm^−1
c = 9.848 (2) Å	T = 298 K
β = 99.560 (6)°	Needle, colorless
V = 5122.3 (19) Å^3	0.54 × 0.21 × 0.16 mm
Z = 8

Data collection

Bruker APEX-II CCD area-detector diffractometer	10949 independent reflections
Radiation source: fine-focus sealed tube	6706 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.000
φ and ω scans	θmax = 26.7°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −60→59
Tmin = 0.802, Tmax = 1.000	k = 0→13
10949 measured reflections	l = 0→12

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.128	H atoms treated by a mixture of independent and constrained refinement
S = 0.95	w = 1/[σ^2(Fo^2) + (0.0667P)^2] where P = (Fo^2 + 2Fc^2)/3
10949 reflections	(Δ/σ)max = 0.001
322 parameters	Δρmax = 0.28 e Å^−3
3 restraints	Δρmin = −0.29 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	Occ. (<1)
Cl	0.054603 (12)	0.42487 (4)	0.32454 (6)	0.06868 (18)
S	0.262469 (13)	−0.14911 (6)	−0.22228 (6)	0.0740 (2)
C1S	0.27896 (7)	−0.0289 (3)	−0.2917 (3)	0.1284 (12)
H1SA	0.2710	0.0458	−0.2663	0.193*
H1SB	0.2759	−0.0359	−0.3903	0.193*
H1SC	0.2990	−0.0305	−0.2570	0.193*
O2S	0.23257 (4)	−0.1473 (2)	−0.28060 (18)	0.1179 (7)
O1S	0.27671 (4)	−0.25807 (16)	−0.25590 (17)	0.1001 (6)
O3S	0.26638 (3)	−0.13174 (14)	−0.07584 (15)	0.0808 (5)
O1W	0.20290 (3)	0.11723 (14)	−0.03723 (18)	0.0715 (4)
H1W2	0.2094 (5)	0.152 (2)	−0.1001 (19)	0.107*
H1W1	0.2126 (5)	0.137 (2)	0.0389 (17)	0.107*
O2	0.15442 (3)	−0.05236 (9)	0.03673 (14)	0.0533 (4)
O31	0.09379 (3)	−0.03223 (11)	0.28673 (15)	0.0644 (4)
O32	0.07754 (3)	0.14309 (11)	0.35473 (14)	0.0595 (4)
O51	0.13789 (4)	0.55636 (12)	0.0734 (3)	0.1273 (9)
O52	0.10095 (3)	0.52961 (10)	0.17372 (14)	0.0604 (4)
N1	0.14330 (3)	0.17363 (11)	0.05256 (15)	0.0457 (4)
H1A	0.1544	0.1384	0.0047	0.055*
N2	0.20709 (4)	−0.13204 (15)	−0.0187 (2)	0.0796 (6)
H2A	0.2197	−0.1485	−0.0733	0.119*
H2B	0.2138	−0.1565	0.0666	0.119*
H2C	0.2040	−0.0528	−0.0186	0.119*
C2	0.12799 (3)	0.10354 (14)	0.12821 (18)	0.0387 (4)
C21	0.13483 (4)	−0.02988 (14)	0.1273 (2)	0.0462 (4)
H21A	0.1429	−0.0559	0.2196	0.055*
H21B	0.1175	−0.0755	0.0978	0.055*
C22	0.15965 (4)	−0.17726 (15)	0.0246 (2)	0.0574 (5)
H22A	0.1420	−0.2187	−0.0114	0.069*
H22B	0.1671	−0.2108	0.1144	0.069*
C23	0.18047 (5)	−0.19490 (19)	−0.0692 (2)	0.0696 (6)
H23A	0.1842	−0.2805	−0.0774	0.083*
H23B	0.1726	−0.1647	−0.1600	0.083*
C3	0.10890 (3)	0.15357 (13)	0.19889 (17)	0.0377 (4)
C31	0.09335 (4)	0.07722 (15)	0.28141 (19)	0.0441 (4)
C32A	0.0570 (4)	0.0537 (11)	0.413 (2)	0.0618 (15)	0.359 (3)
H32A	0.0476	0.0003	0.3410	0.074*	0.359 (3)
H32B	0.0671	0.0053	0.4872	0.074*	0.359 (3)
C33A	0.03650 (15)	0.1329 (7)	0.4621 (8)	0.0893 (11)*	0.359 (3)
H33A	0.0236	0.0856	0.5057	0.134*	0.359 (3)
H33B	0.0260	0.1764	0.3859	0.134*	0.359 (3)
H33C	0.0464	0.1892	0.5274	0.134*	0.359 (3)
C32B	0.0592 (2)	0.0898 (5)	0.4372 (10)	0.0618 (15)	0.641 (3)
H32C	0.0579	0.1411	0.5157	0.074*	0.641 (3)
H32D	0.0667	0.0119	0.4710	0.074*	0.641 (3)
C33B	0.03115 (9)	0.0752 (4)	0.3522 (5)	0.0893 (11)*	0.641 (3)
H33D	0.0190	0.0311	0.4029	0.134*	0.641 (3)
H33E	0.0330	0.0316	0.2699	0.134*	0.641 (3)
H33F	0.0231	0.1533	0.3280	0.134*	0.641 (3)
C4	0.10137 (3)	0.28803 (13)	0.18543 (18)	0.0385 (4)
H4A	0.1022	0.3215	0.2781	0.046*
C41	0.07108 (3)	0.30279 (13)	0.10794 (18)	0.0383 (4)
C42	0.04916 (4)	0.36115 (15)	0.1605 (2)	0.0484 (5)
C43	0.02210 (4)	0.37047 (18)	0.0852 (3)	0.0653 (6)
H43A	0.0079	0.4105	0.1219	0.078*
C44	0.01621 (5)	0.3205 (2)	−0.0438 (3)	0.0727 (6)
H44A	−0.0020	0.3267	−0.0945	0.087*
C45	0.03711 (5)	0.26137 (17)	−0.0984 (2)	0.0621 (6)
H45A	0.0331	0.2273	−0.1857	0.075*
C46	0.06412 (4)	0.25317 (14)	−0.0218 (2)	0.0474 (5)
H46A	0.0781	0.2126	−0.0592	0.057*
C5	0.12288 (3)	0.35592 (14)	0.11441 (19)	0.0420 (4)
C51	0.12205 (4)	0.48857 (16)	0.1153 (2)	0.0557 (5)
C52	0.09665 (5)	0.65791 (16)	0.1763 (2)	0.0702 (6)
H52A	0.0799	0.6750	0.2150	0.105*
H52B	0.0944	0.6891	0.0842	0.105*
H52C	0.1128	0.6953	0.2315	0.105*
C6	0.14174 (4)	0.29802 (14)	0.04932 (19)	0.0436 (4)
C61	0.16244 (4)	0.35578 (17)	−0.0309 (2)	0.0652 (6)
H61A	0.1541	0.4272	−0.0759	0.098*
H61B	0.1670	0.2999	−0.0987	0.098*
H61C	0.1795	0.3771	0.0307	0.098*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl	0.0802 (4)	0.0584 (3)	0.0771 (4)	0.0069 (2)	0.0413 (3)	−0.0126 (3)
S	0.0749 (4)	0.0932 (4)	0.0597 (4)	0.0294 (3)	0.0281 (3)	0.0150 (3)
C1S	0.142 (3)	0.123 (3)	0.138 (3)	0.042 (2)	0.076 (2)	0.067 (2)
O2S	0.0772 (14)	0.205 (2)	0.0718 (13)	0.0308 (12)	0.0138 (10)	0.0125 (13)
O1S	0.1232 (15)	0.1071 (14)	0.0765 (12)	0.0411 (11)	0.0356 (10)	−0.0085 (10)
O3S	0.0986 (13)	0.0925 (11)	0.0569 (10)	0.0276 (8)	0.0293 (9)	0.0058 (9)
O1W	0.0663 (11)	0.0773 (10)	0.0745 (11)	−0.0013 (7)	0.0224 (9)	0.0117 (9)
O2	0.0550 (8)	0.0347 (6)	0.0780 (10)	0.0067 (5)	0.0336 (7)	0.0043 (6)
O31	0.0809 (10)	0.0390 (7)	0.0828 (10)	0.0014 (6)	0.0416 (8)	0.0126 (7)
O32	0.0690 (9)	0.0492 (7)	0.0709 (10)	0.0082 (6)	0.0423 (8)	0.0136 (7)
O51	0.1319 (16)	0.0366 (8)	0.248 (3)	−0.0116 (8)	0.1328 (17)	−0.0016 (11)
O52	0.0755 (9)	0.0323 (7)	0.0826 (10)	0.0002 (6)	0.0400 (8)	−0.0025 (6)
N1	0.0503 (9)	0.0337 (7)	0.0592 (10)	0.0005 (6)	0.0277 (8)	0.0013 (7)
N2	0.0659 (13)	0.0701 (12)	0.1148 (17)	0.0251 (9)	0.0496 (12)	0.0265 (11)
C2	0.0408 (10)	0.0321 (9)	0.0443 (11)	−0.0001 (7)	0.0101 (8)	0.0039 (7)
C21	0.0469 (10)	0.0365 (9)	0.0595 (13)	0.0043 (7)	0.0215 (9)	0.0045 (9)
C22	0.0540 (12)	0.0389 (10)	0.0822 (16)	0.0073 (8)	0.0204 (11)	−0.0022 (10)
C23	0.0788 (17)	0.0596 (13)	0.0736 (16)	0.0244 (11)	0.0224 (13)	−0.0010 (11)
C3	0.0387 (10)	0.0324 (9)	0.0434 (10)	−0.0003 (7)	0.0111 (8)	0.0024 (8)
C31	0.0449 (11)	0.0378 (10)	0.0515 (12)	0.0027 (8)	0.0138 (9)	0.0040 (8)
C32A	0.073 (2)	0.036 (4)	0.089 (4)	0.002 (3)	0.049 (3)	0.006 (3)
C32B	0.073 (2)	0.036 (4)	0.089 (4)	0.002 (3)	0.049 (3)	0.006 (3)
C4	0.0437 (10)	0.0314 (8)	0.0433 (10)	0.0003 (7)	0.0160 (8)	−0.0004 (7)
C41	0.0428 (10)	0.0275 (8)	0.0471 (11)	0.0003 (7)	0.0147 (8)	0.0049 (7)
C42	0.0502 (12)	0.0377 (10)	0.0619 (13)	0.0038 (8)	0.0230 (10)	0.0037 (9)
C43	0.0480 (13)	0.0582 (13)	0.0929 (18)	0.0127 (9)	0.0210 (13)	0.0146 (13)
C44	0.0485 (13)	0.0734 (15)	0.092 (2)	0.0020 (11)	0.0000 (13)	0.0165 (14)
C45	0.0685 (16)	0.0540 (12)	0.0600 (14)	−0.0048 (10)	−0.0006 (12)	0.0077 (10)
C46	0.0523 (12)	0.0376 (9)	0.0541 (12)	0.0019 (8)	0.0140 (10)	0.0059 (9)
C5	0.0419 (10)	0.0327 (9)	0.0534 (11)	−0.0023 (7)	0.0143 (9)	0.0015 (8)
C51	0.0567 (12)	0.0339 (10)	0.0822 (16)	−0.0046 (9)	0.0278 (11)	−0.0018 (10)
C52	0.0888 (17)	0.0360 (10)	0.0910 (17)	0.0084 (10)	0.0299 (13)	−0.0057 (11)
C6	0.0435 (10)	0.0351 (9)	0.0540 (12)	−0.0045 (7)	0.0134 (9)	0.0017 (8)
C61	0.0649 (14)	0.0492 (11)	0.0916 (17)	−0.0041 (9)	0.0428 (12)	0.0087 (11)

Geometric parameters (Å, º)

Cl—C42	1.743 (2)	C3—C4	1.532 (2)
S—O3S	1.4359 (16)	C32A—C33A	1.454 (16)
S—O2S	1.4452 (18)	C32A—H32A	0.9700
S—O1S	1.4489 (16)	C32A—H32B	0.9700
S—C1S	1.742 (3)	C33A—H33A	0.9600
C1S—H1SA	0.9600	C33A—H33B	0.9600
C1S—H1SB	0.9600	C33A—H33C	0.9600
C1S—H1SC	0.9600	C32B—C33B	1.466 (11)
O1W—H1W2	0.830 (15)	C32B—H32C	0.9700
O1W—H1W1	0.842 (15)	C32B—H32D	0.9700
O2—C22	1.413 (2)	C33B—H33D	0.9600
O2—C21	1.4163 (19)	C33B—H33E	0.9600
O31—C31	1.2126 (19)	C33B—H33F	0.9600
O32—C31	1.342 (2)	C4—C41	1.525 (2)
O32—C32B	1.415 (9)	C4—C5	1.531 (2)
O32—C32A	1.567 (17)	C4—H4A	0.9800
O51—C51	1.186 (2)	C41—C46	1.379 (2)
O52—C51	1.319 (2)	C41—C42	1.398 (2)
O52—C52	1.436 (2)	C42—C43	1.381 (3)
N1—C2	1.367 (2)	C43—C44	1.371 (3)
N1—C6	1.379 (2)	C43—H43A	0.9300
N1—H1A	0.8600	C44—C45	1.374 (3)
N2—C23	1.460 (3)	C44—H44A	0.9300
N2—H2A	0.8900	C45—C46	1.383 (3)
N2—H2B	0.8900	C45—H45A	0.9300
N2—H2C	0.8900	C46—H46A	0.9300
C2—C3	1.352 (2)	C5—C6	1.349 (2)
C2—C21	1.513 (2)	C5—C51	1.469 (2)
C21—H21A	0.9700	C52—H52A	0.9600
C21—H21B	0.9700	C52—H52B	0.9600
C22—C23	1.477 (3)	C52—H52C	0.9600
C22—H22A	0.9700	C6—C61	1.505 (2)
C22—H22B	0.9700	C61—H61A	0.9600
C23—H23A	0.9700	C61—H61B	0.9600
C23—H23B	0.9700	C61—H61C	0.9600
C3—C31	1.457 (2)
O3S—S—O2S	110.63 (10)	H32A—C32A—H32B	109.0
O3S—S—O1S	110.68 (10)	O32—C32B—C33B	108.0 (7)
O2S—S—O1S	112.89 (13)	O32—C32B—H32C	110.1
O3S—S—C1S	107.48 (15)	C33B—C32B—H32C	110.1
O2S—S—C1S	108.22 (14)	O32—C32B—H32D	110.1
O1S—S—C1S	106.68 (13)	C33B—C32B—H32D	110.1
S—C1S—H1SA	109.5	H32C—C32B—H32D	108.4
S—C1S—H1SB	109.5	C32B—C33B—H33D	109.5
H1SA—C1S—H1SB	109.5	C32B—C33B—H33E	109.5
S—C1S—H1SC	109.5	H33D—C33B—H33E	109.5
H1SA—C1S—H1SC	109.5	C32B—C33B—H33F	109.5
H1SB—C1S—H1SC	109.5	H33D—C33B—H33F	109.5
H1W2—O1W—H1W1	109 (2)	H33E—C33B—H33F	109.5
C22—O2—C21	111.66 (12)	C41—C4—C5	111.65 (14)
C31—O32—C32B	122.5 (2)	C41—C4—C3	109.64 (12)
C31—O32—C32A	107.1 (5)	C5—C4—C3	110.57 (13)
C51—O52—C52	118.02 (14)	C41—C4—H4A	108.3
C2—N1—C6	123.19 (14)	C5—C4—H4A	108.3
C2—N1—H1A	118.4	C3—C4—H4A	108.3
C6—N1—H1A	118.4	C46—C41—C42	116.55 (16)
C23—N2—H2A	109.5	C46—C41—C4	118.85 (14)
C23—N2—H2B	109.5	C42—C41—C4	124.57 (17)
H2A—N2—H2B	109.5	C43—C42—C41	121.66 (19)
C23—N2—H2C	109.5	C43—C42—Cl	116.69 (15)
H2A—N2—H2C	109.5	C41—C42—Cl	121.65 (15)
H2B—N2—H2C	109.5	C44—C43—C42	119.75 (19)
C3—C2—N1	120.89 (14)	C44—C43—H43A	120.1
C3—C2—C21	124.53 (14)	C42—C43—H43A	120.1
N1—C2—C21	114.56 (14)	C43—C44—C45	120.3 (2)
O2—C21—C2	109.90 (13)	C43—C44—H44A	119.8
O2—C21—H21A	109.7	C45—C44—H44A	119.8
C2—C21—H21A	109.7	C44—C45—C46	119.2 (2)
O2—C21—H21B	109.7	C44—C45—H45A	120.4
C2—C21—H21B	109.7	C46—C45—H45A	120.4
H21A—C21—H21B	108.2	C41—C46—C45	122.54 (17)
O2—C22—C23	109.18 (16)	C41—C46—H46A	118.7
O2—C22—H22A	109.8	C45—C46—H46A	118.7
C23—C22—H22A	109.8	C6—C5—C51	119.89 (15)
O2—C22—H22B	109.8	C6—C5—C4	122.23 (14)
C23—C22—H22B	109.8	C51—C5—C4	117.85 (14)
H22A—C22—H22B	108.3	O51—C51—O52	120.59 (17)
N2—C23—C22	111.09 (19)	O51—C51—C5	127.67 (18)
N2—C23—H23A	109.4	O52—C51—C5	111.72 (14)
C22—C23—H23A	109.4	O52—C52—H52A	109.5
N2—C23—H23B	109.4	O52—C52—H52B	109.5
C22—C23—H23B	109.4	H52A—C52—H52B	109.5
H23A—C23—H23B	108.0	O52—C52—H52C	109.5
C2—C3—C31	119.82 (14)	H52A—C52—H52C	109.5
C2—C3—C4	121.43 (14)	H52B—C52—H52C	109.5
C31—C3—C4	118.56 (14)	C5—C6—N1	120.07 (15)
O31—C31—O32	121.78 (15)	C5—C6—C61	126.44 (15)
O31—C31—C3	126.64 (16)	N1—C6—C61	113.49 (14)
O32—C31—C3	111.59 (14)	C6—C61—H61A	109.5
C33A—C32A—O32	103.7 (8)	C6—C61—H61B	109.5
C33A—C32A—H32A	111.0	H61A—C61—H61B	109.5
O32—C32A—H32A	111.0	C6—C61—H61C	109.5
C33A—C32A—H32B	111.0	H61A—C61—H61C	109.5
O32—C32A—H32B	111.0	H61B—C61—H61C	109.5
C6—N1—C2—C3	3.9 (3)	C5—C4—C41—C42	−115.62 (17)
C6—N1—C2—C21	−174.77 (15)	C3—C4—C41—C42	121.49 (16)
C22—O2—C21—C2	−175.32 (15)	C46—C41—C42—C43	−1.1 (2)
C3—C2—C21—O2	176.55 (17)	C4—C41—C42—C43	−179.42 (16)
N1—C2—C21—O2	−4.8 (2)	C46—C41—C42—Cl	178.43 (12)
C21—O2—C22—C23	−179.18 (18)	C4—C41—C42—Cl	0.1 (2)
O2—C22—C23—N2	58.7 (2)	C41—C42—C43—C44	0.7 (3)
N1—C2—C3—C31	−178.53 (16)	Cl—C42—C43—C44	−178.90 (16)
C21—C2—C3—C31	0.0 (3)	C42—C43—C44—C45	0.0 (3)
N1—C2—C3—C4	6.5 (3)	C43—C44—C45—C46	−0.2 (3)
C21—C2—C3—C4	−174.98 (15)	C42—C41—C46—C45	1.0 (2)
C32B—O32—C31—O31	−3.4 (6)	C4—C41—C46—C45	179.35 (15)
C32A—O32—C31—O31	−12.0 (9)	C44—C45—C46—C41	−0.3 (3)
C32B—O32—C31—C3	176.4 (5)	C41—C4—C5—C6	−109.78 (19)
C32A—O32—C31—C3	167.8 (9)	C3—C4—C5—C6	12.6 (2)
C2—C3—C31—O31	−6.4 (3)	C41—C4—C5—C51	68.5 (2)
C4—C3—C31—O31	168.79 (18)	C3—C4—C5—C51	−169.11 (15)
C2—C3—C31—O32	173.84 (17)	C52—O52—C51—O51	4.2 (3)
C4—C3—C31—O32	−11.0 (2)	C52—O52—C51—C5	−177.16 (16)
C31—O32—C32A—C33A	−167.2 (9)	C6—C5—C51—O51	−6.6 (3)
C32B—O32—C32A—C33A	38 (3)	C4—C5—C51—O51	175.1 (2)
C31—O32—C32B—C33B	−90.5 (6)	C6—C5—C51—O52	174.95 (18)
C32A—O32—C32B—C33B	−62 (4)	C4—C5—C51—O52	−3.4 (2)
C2—C3—C4—C41	109.83 (18)	C51—C5—C6—N1	177.62 (16)
C31—C3—C4—C41	−65.2 (2)	C4—C5—C6—N1	−4.1 (3)
C2—C3—C4—C5	−13.7 (2)	C51—C5—C6—C61	−2.4 (3)
C31—C3—C4—C5	171.23 (16)	C4—C5—C6—C61	175.90 (19)
C5—C4—C41—C46	66.13 (18)	C2—N1—C6—C5	−5.2 (3)
C3—C4—C41—C46	−56.76 (19)	C2—N1—C6—C61	174.84 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W2···O1S^i	0.83 (2)	1.94 (2)	2.767 (2)	176 (3)
O1W—H1W1···O2S^ii	0.84 (2)	1.88 (2)	2.704 (3)	168 (2)
N1—H1A···O2	0.86	2.14	2.5670 (17)	111
N1—H1A···O1W	0.86	2.42	3.174 (2)	146
N2—H2A···O2S	0.89	2.23	3.032 (3)	150
N2—H2A···O3S	0.89	2.24	2.971 (2)	140
N2—H2A···S	0.89	2.70	3.5744 (18)	167
N2—H2B···O1S^iii	0.89	2.07	2.949 (3)	168
N2—H2B···O3S^iii	0.89	2.52	2.985 (2)	113
N2—H2B···S^iii	0.89	2.77	3.5299 (19)	144
N2—H2C···O1W	0.89	1.89	2.770 (2)	169

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