Solvates of acoti­amide hydro­chloride: characterization and phase transformation

Five novel crystals of acoti­amide hydro­chloride (AH) with solvates dimethyl formide (DMF), dimethyl sulfoxide (DMSO), ethyl acetate (EA) and water (W) [1AH-1W-1DMF, 1AH-1DMSO-I, 1AH-1DMSO-II, 1AH-1W-1DMSO and 2AH-2DMSO-1EA] were characterized using single-crystal X-ray diffraction, powder X-ray diffraction, thermal analysis and Fourier transform infrared spectroscopy. The five crystals can be divided into four distinct structural types based on analysis of their similarities; 1AH-1W-1DMF and 1AH-1W-1DMSO are isostructural. The benzene rings in 1AH-1DMSO-I, 1AH-1DMSO-II and 2AH-2DMSO-1EA can rotate 180°, and the intramolecular hydrogen bond changes from an OH...C=O bond to an NH...OH bond relative to what is seen in 1AH-1W-1DMF and 1AH-1W-1DMSO. Phase transformation experiments show that a humidity-induced phase transformation is closely tied to moisture content.

Computing details

For all structures, program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2014).

(1AH-1W-1DMF)

Crystal data

C21H31N4O5S·Cl·C3H7NO·H2O	F(000) = 1232
Mr = 578.12	Dx = 1.299 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
a = 16.6380 (4) Å	Cell parameters from 5401 reflections
b = 12.0355 (3) Å	θ = 4.6–68.4°
c = 15.4979 (4) Å	µ = 2.22 mm^−1
β = 107.668 (1)°	T = 293 K
V = 2957.02 (13) Å^3	Prism, colorless
Z = 4	0.15 × 0.08 × 0.06 mm

Data collection

CCD diffractometer	4460 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.051
ωκ scans	θmax = 68.4°, θmin = 4.6°
Absorption correction: multi-scan Higashi, T. (1995)	h = −20→20
Tmin = 0.808, Tmax = 0.875	k = −14→14
32662 measured reflections	l = −18→18
5401 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.052	w = 1/[σ^2(Fo^2) + (0.0865P)^2 + 1.6052P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.156	(Δ/σ)max < 0.001
S = 1.03	Δρmax = 0.67 e Å^−3
5401 reflections	Δρmin = −0.42 e Å^−3
368 parameters	Extinction correction: SHELXL-2014/7 (Sheldrick 2014, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0043 (5)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.08378 (4)	0.70299 (5)	0.36818 (5)	0.0472 (2)
Cl1	0.37520 (5)	0.94069 (6)	0.23728 (6)	0.0723 (3)
O1	−0.09494 (13)	1.0470 (2)	0.40757 (17)	0.0661 (6)
O2	−0.01165 (14)	1.41862 (16)	0.37066 (15)	0.0664 (6)
O3	0.11771 (12)	1.35191 (14)	0.32710 (14)	0.0569 (5)
O4	−0.00171 (11)	0.88911 (15)	0.37959 (13)	0.0541 (5)
O5	0.32158 (13)	0.52546 (16)	0.34877 (18)	0.0742 (6)
O6	0.64419 (18)	0.6978 (2)	0.0269 (2)	0.0989 (9)
O7	0.74040 (14)	0.55606 (19)	0.1659 (2)	0.0652 (6)
N1	0.12198 (12)	0.92411 (16)	0.35492 (14)	0.0423 (5)
N2	0.21763 (12)	0.78767 (15)	0.34433 (13)	0.0417 (4)
N3	0.36354 (13)	0.69980 (18)	0.33057 (15)	0.0471 (5)
N4	0.43294 (11)	0.72211 (16)	0.16515 (13)	0.0382 (4)
N5	0.73395 (16)	0.7731 (3)	−0.03944 (18)	0.0722 (7)
C1	−0.03946 (15)	1.1162 (2)	0.38785 (18)	0.0472 (6)
C2	−0.05497 (16)	1.2297 (2)	0.39029 (19)	0.0530 (6)
H2B	−0.1019	1.2541	0.4055	0.064*
C3	−0.00172 (16)	1.3062 (2)	0.37043 (17)	0.0472 (6)
C4	0.06891 (14)	1.2700 (2)	0.34662 (16)	0.0430 (5)
C5	0.08468 (14)	1.15856 (19)	0.34453 (16)	0.0411 (5)
H5A	0.1315	1.1350	0.3286	0.049*
C6	0.03175 (13)	1.07873 (19)	0.36588 (16)	0.0399 (5)
C7	0.04824 (14)	0.95919 (19)	0.36684 (16)	0.0409 (5)
C8	0.14502 (13)	0.81393 (18)	0.35454 (15)	0.0383 (5)
C9	0.16218 (17)	0.6151 (2)	0.35991 (19)	0.0509 (6)
H9A	0.1602	0.5381	0.3631	0.061*
C10	0.22729 (15)	0.67390 (19)	0.34816 (17)	0.0436 (5)
C11	0.30749 (16)	0.6252 (2)	0.34143 (18)	0.0472 (6)
C12	0.44635 (15)	0.6682 (2)	0.32655 (17)	0.0490 (6)
H12A	0.4679	0.6089	0.3697	0.059*
H12B	0.4840	0.7313	0.3448	0.059*
C13	0.44770 (15)	0.62993 (19)	0.23395 (17)	0.0453 (5)
H13A	0.5019	0.5959	0.2397	0.054*
H13B	0.4047	0.5736	0.2120	0.054*
C14	0.36427 (16)	0.6944 (2)	0.07748 (18)	0.0532 (6)
H14A	0.3578	0.7593	0.0378	0.064*
C15	0.28077 (17)	0.6776 (3)	0.0966 (2)	0.0765 (10)
H15A	0.2686	0.7417	0.1273	0.115*
H15B	0.2367	0.6674	0.0406	0.115*
H15C	0.2843	0.6132	0.1341	0.115*
C16	0.3898 (2)	0.5978 (3)	0.0290 (2)	0.0815 (10)
H16A	0.4428	0.6140	0.0192	0.122*
H16B	0.3952	0.5320	0.0653	0.122*
H16C	0.3475	0.5862	−0.0282	0.122*
C17	0.51444 (14)	0.7619 (2)	0.14868 (18)	0.0492 (6)
H17A	0.5379	0.7005	0.1224	0.059*
C18	0.57832 (18)	0.7952 (3)	0.2370 (2)	0.0710 (9)
H18A	0.5891	0.7333	0.2780	0.107*
H18B	0.6298	0.8172	0.2261	0.107*
H18C	0.5566	0.8562	0.2631	0.107*
C19	0.4959 (2)	0.8581 (3)	0.0821 (2)	0.0660 (8)
H19A	0.4552	0.8352	0.0265	0.099*
H19B	0.4738	0.9194	0.1073	0.099*
H19C	0.5470	0.8804	0.0703	0.099*
C20	−0.0872 (3)	1.4596 (3)	0.3852 (3)	0.0864 (11)
H20A	−0.0871	1.5393	0.3839	0.130*
H20B	−0.1353	1.4323	0.3384	0.130*
H20C	−0.0900	1.4346	0.4431	0.130*
C21	0.17281 (18)	1.3217 (2)	0.2766 (2)	0.0590 (7)
H21A	0.2033	1.3861	0.2675	0.089*
H21B	0.2119	1.2665	0.3093	0.089*
H21C	0.1405	1.2922	0.2190	0.089*
C22	0.6777 (3)	0.7763 (4)	0.0017 (3)	0.0971 (12)
H22A	0.6605	0.8466	0.0137	0.116*
C23	0.7618 (3)	0.6613 (5)	−0.0600 (3)	0.1096 (15)
H23A	0.8037	0.6694	−0.0906	0.164*
H23B	0.7853	0.6211	−0.0045	0.164*
H23C	0.7143	0.6213	−0.0980	0.164*
C24	0.7746 (4)	0.8619 (6)	−0.0652 (4)	0.174 (3)
H24A	0.8136	0.8345	−0.0949	0.261*
H24B	0.7337	0.9088	−0.1061	0.261*
H24C	0.8047	0.9037	−0.0126	0.261*
H1B	0.4099 (17)	0.780 (2)	0.1883 (19)	0.053 (8)*
H1A	0.1584 (18)	0.967 (3)	0.3511 (19)	0.052 (8)*
H3A	0.3486 (19)	0.766 (3)	0.322 (2)	0.061 (9)*
H1C	−0.084 (2)	0.984 (3)	0.405 (2)	0.070 (11)*
H7A	0.709 (2)	0.589 (3)	0.125 (3)	0.075 (13)*
H7B	0.716 (2)	0.523 (3)	0.189 (3)	0.079 (12)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0454 (3)	0.0355 (3)	0.0649 (4)	−0.0042 (2)	0.0230 (3)	−0.0002 (2)
Cl1	0.0865 (5)	0.0404 (4)	0.1148 (7)	−0.0021 (3)	0.0676 (5)	−0.0066 (3)
O1	0.0519 (11)	0.0587 (13)	0.1012 (17)	−0.0008 (9)	0.0435 (11)	−0.0020 (11)
O2	0.0786 (13)	0.0429 (10)	0.0896 (15)	0.0225 (9)	0.0434 (11)	0.0025 (9)
O3	0.0668 (11)	0.0346 (9)	0.0812 (13)	0.0027 (8)	0.0403 (10)	−0.0007 (8)
O4	0.0461 (9)	0.0428 (9)	0.0778 (13)	−0.0062 (7)	0.0256 (9)	−0.0038 (8)
O5	0.0661 (12)	0.0357 (10)	0.130 (2)	0.0126 (9)	0.0444 (13)	0.0096 (11)
O6	0.0973 (18)	0.0911 (19)	0.130 (2)	0.0030 (15)	0.0666 (18)	0.0332 (16)
O7	0.0524 (12)	0.0493 (12)	0.1046 (19)	−0.0056 (9)	0.0398 (13)	0.0075 (12)
N1	0.0372 (10)	0.0311 (10)	0.0615 (13)	0.0008 (8)	0.0195 (9)	0.0010 (8)
N2	0.0415 (10)	0.0321 (10)	0.0539 (12)	0.0007 (8)	0.0179 (9)	−0.0008 (8)
N3	0.0509 (11)	0.0374 (11)	0.0587 (13)	0.0077 (9)	0.0254 (10)	0.0055 (9)
N4	0.0356 (9)	0.0351 (10)	0.0457 (11)	−0.0017 (7)	0.0150 (8)	−0.0048 (8)
N5	0.0632 (15)	0.095 (2)	0.0617 (15)	−0.0124 (14)	0.0244 (12)	0.0118 (14)
C1	0.0401 (12)	0.0495 (14)	0.0558 (14)	0.0026 (10)	0.0204 (11)	−0.0017 (11)
C2	0.0463 (13)	0.0571 (15)	0.0624 (16)	0.0160 (11)	0.0267 (12)	−0.0017 (12)
C3	0.0535 (13)	0.0411 (13)	0.0489 (14)	0.0139 (11)	0.0180 (11)	−0.0004 (10)
C4	0.0436 (12)	0.0389 (12)	0.0476 (13)	0.0051 (10)	0.0154 (10)	−0.0018 (10)
C5	0.0365 (11)	0.0386 (12)	0.0503 (13)	0.0076 (9)	0.0163 (9)	−0.0004 (10)
C6	0.0333 (10)	0.0386 (12)	0.0471 (13)	0.0052 (9)	0.0113 (9)	−0.0010 (9)
C7	0.0367 (11)	0.0396 (12)	0.0461 (13)	0.0003 (9)	0.0121 (9)	−0.0019 (9)
C8	0.0396 (11)	0.0323 (11)	0.0426 (12)	−0.0003 (9)	0.0119 (9)	0.0000 (9)
C9	0.0568 (14)	0.0310 (12)	0.0689 (17)	0.0001 (10)	0.0251 (12)	0.0005 (11)
C10	0.0476 (12)	0.0315 (11)	0.0537 (14)	0.0037 (9)	0.0186 (10)	0.0024 (9)
C11	0.0501 (13)	0.0361 (12)	0.0589 (15)	0.0070 (10)	0.0216 (11)	0.0020 (10)
C12	0.0429 (12)	0.0533 (14)	0.0524 (14)	0.0091 (11)	0.0168 (11)	0.0081 (11)
C13	0.0444 (12)	0.0378 (12)	0.0556 (14)	0.0066 (10)	0.0177 (11)	0.0016 (10)
C14	0.0487 (13)	0.0611 (16)	0.0461 (14)	−0.0101 (12)	0.0089 (11)	−0.0066 (11)
C15	0.0441 (15)	0.107 (3)	0.072 (2)	−0.0167 (16)	0.0076 (14)	−0.0087 (18)
C16	0.092 (2)	0.082 (2)	0.071 (2)	−0.0200 (19)	0.0250 (18)	−0.0360 (18)
C17	0.0396 (12)	0.0554 (15)	0.0589 (15)	−0.0069 (11)	0.0242 (11)	−0.0088 (12)
C18	0.0445 (14)	0.094 (2)	0.073 (2)	−0.0210 (15)	0.0154 (13)	−0.0083 (17)
C19	0.0697 (18)	0.0659 (18)	0.0725 (19)	−0.0162 (15)	0.0367 (15)	0.0019 (15)
C20	0.105 (3)	0.063 (2)	0.114 (3)	0.0418 (19)	0.066 (2)	0.0094 (19)
C21	0.0598 (16)	0.0460 (14)	0.082 (2)	0.0074 (12)	0.0383 (14)	0.0090 (13)
C22	0.095 (3)	0.102 (3)	0.101 (3)	0.007 (2)	0.040 (2)	0.017 (2)
C23	0.101 (3)	0.143 (4)	0.088 (3)	0.019 (3)	0.033 (2)	−0.002 (3)
C24	0.133 (4)	0.231 (7)	0.136 (5)	−0.088 (5)	0.006 (3)	0.093 (5)

Geometric parameters (Å, º)

S1—C9	1.714 (3)	C9—H9A	0.9300
S1—C8	1.731 (2)	C10—C11	1.490 (3)
O1—C1	1.346 (3)	C12—C13	1.514 (4)
O1—H1C	0.79 (4)	C12—H12A	0.9700
O2—C3	1.363 (3)	C12—H12B	0.9700
O2—C20	1.431 (4)	C13—H13A	0.9700
O3—C4	1.368 (3)	C13—H13B	0.9700
O3—C21	1.421 (3)	C14—C16	1.513 (4)
O4—C7	1.241 (3)	C14—C15	1.519 (4)
O5—C11	1.222 (3)	C14—H14A	0.9800
O6—C22	1.220 (5)	C15—H15A	0.9600
O7—H7A	0.79 (4)	C15—H15B	0.9600
O7—H7B	0.73 (4)	C15—H15C	0.9600
N1—C7	1.362 (3)	C16—H16A	0.9600
N1—C8	1.381 (3)	C16—H16B	0.9600
N1—H1A	0.82 (3)	C16—H16C	0.9600
N2—C8	1.304 (3)	C17—C18	1.510 (4)
N2—C10	1.378 (3)	C17—C19	1.518 (4)
N3—C11	1.342 (3)	C17—H17A	0.9800
N3—C12	1.449 (3)	C18—H18A	0.9600
N3—H3A	0.84 (3)	C18—H18B	0.9600
N4—C13	1.506 (3)	C18—H18C	0.9600
N4—C14	1.523 (3)	C19—H19A	0.9600
N4—C17	1.531 (3)	C19—H19B	0.9600
N4—H1B	0.92 (3)	C19—H19C	0.9600
N5—C22	1.282 (5)	C20—H20A	0.9600
N5—C24	1.387 (5)	C20—H20B	0.9600
N5—C23	1.489 (6)	C20—H20C	0.9600
C1—C2	1.393 (4)	C21—H21A	0.9600
C1—C6	1.403 (3)	C21—H21B	0.9600
C2—C3	1.375 (4)	C21—H21C	0.9600
C2—H2B	0.9300	C22—H22A	0.9300
C3—C4	1.404 (3)	C23—H23A	0.9600
C4—C5	1.369 (3)	C23—H23B	0.9600
C5—C6	1.409 (3)	C23—H23C	0.9600
C5—H5A	0.9300	C24—H24A	0.9600
C6—C7	1.464 (3)	C24—H24B	0.9600
C9—C10	1.351 (3)	C24—H24C	0.9600
C9—S1—C8	88.69 (11)	H13A—C13—H13B	107.7
C1—O1—H1C	114 (3)	C16—C14—C15	113.9 (3)
C3—O2—C20	117.1 (2)	C16—C14—N4	111.3 (2)
C4—O3—C21	117.57 (19)	C15—C14—N4	109.7 (2)
H7A—O7—H7B	110 (4)	C16—C14—H14A	107.2
C7—N1—C8	124.1 (2)	C15—C14—H14A	107.2
C7—N1—H1A	122 (2)	N4—C14—H14A	107.2
C8—N1—H1A	114 (2)	C14—C15—H15A	109.5
C8—N2—C10	109.63 (19)	C14—C15—H15B	109.5
C11—N3—C12	122.4 (2)	H15A—C15—H15B	109.5
C11—N3—H3A	118 (2)	C14—C15—H15C	109.5
C12—N3—H3A	119 (2)	H15A—C15—H15C	109.5
C13—N4—C14	112.77 (19)	H15B—C15—H15C	109.5
C13—N4—C17	112.72 (18)	C14—C16—H16A	109.5
C14—N4—C17	112.48 (18)	C14—C16—H16B	109.5
C13—N4—H1B	106.4 (18)	H16A—C16—H16B	109.5
C14—N4—H1B	103.0 (17)	C14—C16—H16C	109.5
C17—N4—H1B	108.7 (17)	H16A—C16—H16C	109.5
C22—N5—C24	127.9 (5)	H16B—C16—H16C	109.5
C22—N5—C23	117.0 (4)	C18—C17—C19	110.8 (2)
C24—N5—C23	115.1 (4)	C18—C17—N4	110.3 (2)
O1—C1—C2	117.1 (2)	C19—C17—N4	110.1 (2)
O1—C1—C6	123.0 (2)	C18—C17—H17A	108.5
C2—C1—C6	119.9 (2)	C19—C17—H17A	108.5
C3—C2—C1	120.9 (2)	N4—C17—H17A	108.5
C3—C2—H2B	119.6	C17—C18—H18A	109.5
C1—C2—H2B	119.6	C17—C18—H18B	109.5
O2—C3—C2	125.2 (2)	H18A—C18—H18B	109.5
O2—C3—C4	114.9 (2)	C17—C18—H18C	109.5
C2—C3—C4	119.9 (2)	H18A—C18—H18C	109.5
O3—C4—C5	124.7 (2)	H18B—C18—H18C	109.5
O3—C4—C3	115.8 (2)	C17—C19—H19A	109.5
C5—C4—C3	119.5 (2)	C17—C19—H19B	109.5
C4—C5—C6	121.6 (2)	H19A—C19—H19B	109.5
C4—C5—H5A	119.2	C17—C19—H19C	109.5
C6—C5—H5A	119.2	H19A—C19—H19C	109.5
C1—C6—C5	118.1 (2)	H19B—C19—H19C	109.5
C1—C6—C7	118.9 (2)	O2—C20—H20A	109.5
C5—C6—C7	123.0 (2)	O2—C20—H20B	109.5
O4—C7—N1	119.0 (2)	H20A—C20—H20B	109.5
O4—C7—C6	122.5 (2)	O2—C20—H20C	109.5
N1—C7—C6	118.5 (2)	H20A—C20—H20C	109.5
N2—C8—N1	120.1 (2)	H20B—C20—H20C	109.5
N2—C8—S1	115.42 (17)	O3—C21—H21A	109.5
N1—C8—S1	124.45 (17)	O3—C21—H21B	109.5
C10—C9—S1	110.29 (18)	H21A—C21—H21B	109.5
C10—C9—H9A	124.9	O3—C21—H21C	109.5
S1—C9—H9A	124.9	H21A—C21—H21C	109.5
C9—C10—N2	116.0 (2)	H21B—C21—H21C	109.5
C9—C10—C11	125.1 (2)	O6—C22—N5	127.6 (5)
N2—C10—C11	118.9 (2)	O6—C22—H22A	116.2
O5—C11—N3	123.3 (2)	N5—C22—H22A	116.2
O5—C11—C10	122.1 (2)	N5—C23—H23A	109.5
N3—C11—C10	114.6 (2)	N5—C23—H23B	109.5
N3—C12—C13	114.1 (2)	H23A—C23—H23B	109.5
N3—C12—H12A	108.7	N5—C23—H23C	109.5
C13—C12—H12A	108.7	H23A—C23—H23C	109.5
N3—C12—H12B	108.7	H23B—C23—H23C	109.5
C13—C12—H12B	108.7	N5—C24—H24A	109.5
H12A—C12—H12B	107.6	N5—C24—H24B	109.5
N4—C13—C12	113.61 (19)	H24A—C24—H24B	109.5
N4—C13—H13A	108.8	N5—C24—H24C	109.5
C12—C13—H13A	108.8	H24A—C24—H24C	109.5
N4—C13—H13B	108.8	H24B—C24—H24C	109.5
C12—C13—H13B	108.8
O1—C1—C2—C3	−179.6 (2)	C7—N1—C8—S1	0.5 (3)
C6—C1—C2—C3	0.7 (4)	C9—S1—C8—N2	0.2 (2)
C20—O2—C3—C2	−5.6 (4)	C9—S1—C8—N1	−179.1 (2)
C20—O2—C3—C4	173.7 (3)	C8—S1—C9—C10	0.2 (2)
C1—C2—C3—O2	179.8 (3)	S1—C9—C10—N2	−0.7 (3)
C1—C2—C3—C4	0.5 (4)	S1—C9—C10—C11	177.8 (2)
C21—O3—C4—C5	19.3 (4)	C8—N2—C10—C9	0.8 (3)
C21—O3—C4—C3	−160.9 (2)	C8—N2—C10—C11	−177.8 (2)
O2—C3—C4—O3	0.0 (3)	C12—N3—C11—O5	0.0 (4)
C2—C3—C4—O3	179.3 (2)	C12—N3—C11—C10	177.4 (2)
O2—C3—C4—C5	179.9 (2)	C9—C10—C11—O5	−2.1 (4)
C2—C3—C4—C5	−0.8 (4)	N2—C10—C11—O5	176.4 (3)
O3—C4—C5—C6	179.7 (2)	C9—C10—C11—N3	−179.5 (3)
C3—C4—C5—C6	−0.1 (4)	N2—C10—C11—N3	−1.0 (3)
O1—C1—C6—C5	178.7 (2)	C11—N3—C12—C13	83.1 (3)
C2—C1—C6—C5	−1.6 (4)	C14—N4—C13—C12	−129.2 (2)
O1—C1—C6—C7	−1.8 (4)	C17—N4—C13—C12	102.1 (2)
C2—C1—C6—C7	177.9 (2)	N3—C12—C13—N4	70.5 (3)
C4—C5—C6—C1	1.3 (4)	C13—N4—C14—C16	−64.8 (3)
C4—C5—C6—C7	−178.2 (2)	C17—N4—C14—C16	64.0 (3)
C8—N1—C7—O4	1.1 (4)	C13—N4—C14—C15	62.2 (3)
C8—N1—C7—C6	179.9 (2)	C17—N4—C14—C15	−168.9 (2)
C1—C6—C7—O4	5.6 (4)	C13—N4—C17—C18	−54.8 (3)
C5—C6—C7—O4	−174.9 (2)	C14—N4—C17—C18	176.4 (2)
C1—C6—C7—N1	−173.1 (2)	C13—N4—C17—C19	−177.4 (2)
C5—C6—C7—N1	6.3 (4)	C14—N4—C17—C19	53.7 (3)
C10—N2—C8—N1	178.7 (2)	C24—N5—C22—O6	−177.4 (5)
C10—N2—C8—S1	−0.6 (3)	C23—N5—C22—O6	0.5 (7)
C7—N1—C8—N2	−178.7 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O7^i	0.82 (3)	2.08 (3)	2.884 (3)	171 (3)
N3—H3A···Cl1	0.84 (3)	2.59 (3)	3.272 (2)	140 (3)
N4—H1B···Cl1	0.92 (3)	2.21 (3)	3.122 (2)	168 (2)
O1—H1C···O4	0.79 (4)	1.91 (4)	2.572 (3)	141 (3)
O7—H7A···O6	0.79 (4)	2.05 (4)	2.832 (4)	169 (4)
O7—H7B···Cl1^ii	0.73 (4)	2.38 (4)	3.104 (2)	171 (4)

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

(1AH-1DMSO-I)

Crystal data

C21H31N4O5S·Cl·C2H6OS	Z = 2
Mr = 565.13	F(000) = 600
Triclinic, P1	Dx = 1.310 Mg m^−3
a = 8.0881 (4) Å	Cu Kα radiation, λ = 1.54184 Å
b = 11.2760 (7) Å	Cell parameters from 9180 reflections
c = 16.2993 (11) Å	θ = 4.1–72.5°
α = 98.210 (5)°	µ = 2.90 mm^−1
β = 95.377 (5)°	T = 293 K
γ = 101.106 (5)°	Prism, colorless
V = 1432.45 (15) Å^3	0.13 × 0.06 × 0.05 mm

Data collection

CCD diffractometer	4248 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.026
ωκ scans	θmax = 72.5°, θmin = 4.1°
Absorption correction: multi-scan Higashi, T. (1995)	h = −9→7
Tmin = 0.811, Tmax = 0.865	k = −13→13
9180 measured reflections	l = −19→20
5498 independent reflections

Refinement

Refinement on F^2	3 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.055	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.163	w = 1/[σ^2(Fo^2) + (0.0763P)^2 + 0.4697P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
5498 reflections	Δρmax = 0.45 e Å^−3
384 parameters	Δρmin = −0.45 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	0.44526 (10)	0.84658 (6)	0.79992 (5)	0.0640 (2)
Cl1	0.36596 (9)	0.84748 (6)	0.24716 (5)	0.0652 (2)
N1	0.5098 (3)	0.6174 (2)	0.75577 (14)	0.0523 (5)
N2	0.6484 (3)	0.74055 (18)	0.87944 (13)	0.0477 (5)
N3	0.8399 (3)	0.8096 (2)	1.03441 (14)	0.0563 (6)
N4	0.9870 (3)	0.8766 (2)	1.26587 (13)	0.0511 (5)
O1	0.5613 (3)	0.3922 (2)	0.72034 (14)	0.0727 (6)
O2	0.3542 (3)	0.1743 (3)	0.4427 (2)	0.1309 (15)
O3	0.2051 (3)	0.3462 (3)	0.40740 (15)	0.0919 (8)
O4	0.3197 (3)	0.6695 (2)	0.66540 (14)	0.0743 (6)
O5	0.8072 (3)	1.00495 (17)	1.03903 (13)	0.0660 (5)
C1	0.4741 (3)	0.3846 (3)	0.64323 (18)	0.0560 (6)
C2	0.4615 (4)	0.2814 (3)	0.5823 (2)	0.0697 (8)
H2B	0.5139	0.2183	0.5944	0.084*
C3	0.3723 (4)	0.2719 (3)	0.5045 (2)	0.0736 (9)
C4	0.2914 (3)	0.3647 (3)	0.48611 (18)	0.0665 (8)
C5	0.3066 (3)	0.4675 (3)	0.54536 (17)	0.0565 (6)
H5A	0.2552	0.5307	0.5324	0.068*
C6	0.3980 (3)	0.4795 (2)	0.62514 (16)	0.0507 (6)
C7	0.4039 (3)	0.5956 (2)	0.68261 (17)	0.0527 (6)
C8	0.5412 (3)	0.7251 (2)	0.81262 (15)	0.0463 (5)
C9	0.5620 (4)	0.9245 (3)	0.89192 (18)	0.0622 (7)
C10	0.6603 (3)	0.8561 (2)	0.92437 (15)	0.0480 (5)
C11	0.7758 (3)	0.8978 (2)	1.00448 (16)	0.0506 (6)
C12	0.9584 (4)	0.8355 (3)	1.10996 (16)	0.0563 (6)
H12A	1.0426	0.9093	1.1095	0.068*
H12B	1.0169	0.7684	1.1125	0.068*
C13	0.8665 (3)	0.8523 (3)	1.18583 (16)	0.0554 (6)
H13A	0.7804	0.7792	1.1853	0.066*
H13B	0.8099	0.9204	1.1836	0.066*
C14	0.9385 (4)	0.7786 (3)	1.3198 (2)	0.0692 (8)
H14A	0.8203	0.7753	1.3299	0.083*
C15	0.9510 (5)	0.6550 (3)	1.2734 (3)	0.0886 (11)
H15A	0.8805	0.6382	1.2206	0.133*
H15B	1.0667	0.6559	1.2642	0.133*
H15C	0.9137	0.5926	1.3059	0.133*
C16	1.0491 (5)	0.8073 (4)	1.4037 (2)	0.0895 (12)
H16A	1.0398	0.8858	1.4324	0.134*
H16B	1.0122	0.7455	1.4367	0.134*
H16C	1.1652	0.8088	1.3951	0.134*
C17	1.0133 (4)	1.0081 (3)	1.31024 (17)	0.0589 (7)
H17A	1.1031	1.0191	1.3571	0.071*
C18	1.0771 (5)	1.0951 (3)	1.2526 (2)	0.0717 (8)
H18A	1.1768	1.0745	1.2317	0.108*
H18B	0.9906	1.0889	1.2067	0.108*
H18C	1.1044	1.1775	1.2827	0.108*
C19	0.8551 (5)	1.0329 (4)	1.3469 (2)	0.0836 (10)
H19A	0.8213	0.9746	1.3828	0.125*
H19B	0.8788	1.1143	1.3785	0.125*
H19C	0.7650	1.0257	1.3025	0.125*
C20	0.4702 (6)	0.1133 (4)	0.4326 (3)	0.1171 (17)
H20A	0.4327	0.0483	0.3858	0.176*
H20B	0.5713	0.1664	0.4222	0.176*
H20C	0.4940	0.0792	0.4820	0.176*
C21	0.1159 (5)	0.4345 (4)	0.3862 (2)	0.0925 (12)
H21A	0.0614	0.4100	0.3297	0.139*
H21B	0.1935	0.5119	0.3910	0.139*
H21C	0.0317	0.4422	0.4232	0.139*
S2A	0.2876 (3)	0.56974 (17)	0.94913 (16)	0.1287 (11)	0.650 (4)
O6A	0.207 (2)	0.4425 (14)	0.9383 (9)	0.124 (4)	0.650 (4)
C22A	0.127 (4)	0.655 (2)	0.924 (2)	0.214 (16)	0.650 (4)
H22A	0.1780	0.7404	0.9305	0.322*	0.650 (4)
H22B	0.0765	0.6263	0.8668	0.322*	0.650 (4)
H22C	0.0409	0.6429	0.9603	0.322*	0.650 (4)
C23A	0.334 (2)	0.6287 (16)	1.0529 (12)	0.252 (11)	0.650 (4)
H23A	0.3877	0.7138	1.0596	0.377*	0.650 (4)
H23B	0.2310	0.6206	1.0785	0.377*	0.650 (4)
H23C	0.4091	0.5850	1.0791	0.377*	0.650 (4)
S2B	0.2043 (5)	0.5749 (3)	1.0160 (3)	0.1147 (17)	0.350 (4)
O6B	0.186 (3)	0.453 (2)	0.9655 (15)	0.099 (5)	0.350 (4)
C22B	0.170 (5)	0.665 (3)	0.939 (3)	0.115 (7)	0.350 (4)
H22D	0.0504	0.6582	0.9256	0.172*	0.350 (4)
H22E	0.2175	0.6360	0.8902	0.172*	0.350 (4)
H22F	0.2238	0.7485	0.9600	0.172*	0.350 (4)
C23B	0.422 (2)	0.647 (3)	1.0547 (14)	0.161 (11)	0.350 (4)
H23D	0.4256	0.7261	1.0871	0.242*	0.350 (4)
H23E	0.4698	0.5971	1.0892	0.242*	0.350 (4)
H23F	0.4856	0.6572	1.0085	0.242*	0.350 (4)
H4A	1.083 (4)	0.868 (3)	1.2556 (18)	0.046 (7)*
H1B	0.561 (4)	0.560 (3)	0.7657 (18)	0.053 (8)*
H1A	0.580 (5)	0.320 (4)	0.732 (3)	0.093 (13)*
H3A	0.808 (4)	0.739 (3)	1.016 (2)	0.061 (9)*
H9A	0.555 (4)	1.003 (3)	0.912 (2)	0.065 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0752 (5)	0.0534 (4)	0.0598 (4)	0.0255 (3)	−0.0169 (3)	−0.0026 (3)
Cl1	0.0640 (4)	0.0477 (3)	0.0827 (5)	0.0151 (3)	0.0047 (3)	0.0054 (3)
N1	0.0634 (13)	0.0418 (11)	0.0467 (11)	0.0107 (9)	−0.0062 (9)	−0.0006 (9)
N2	0.0569 (11)	0.0401 (10)	0.0429 (10)	0.0097 (8)	−0.0020 (9)	0.0023 (8)
N3	0.0724 (14)	0.0447 (12)	0.0451 (11)	0.0127 (10)	−0.0096 (10)	−0.0046 (9)
N4	0.0447 (11)	0.0622 (13)	0.0440 (11)	0.0092 (9)	−0.0005 (9)	0.0076 (9)
O1	0.0980 (16)	0.0491 (11)	0.0642 (12)	0.0236 (11)	−0.0194 (11)	−0.0057 (9)
O2	0.0745 (16)	0.145 (3)	0.135 (3)	0.0399 (17)	−0.0334 (16)	−0.097 (2)
O3	0.0814 (15)	0.114 (2)	0.0621 (14)	0.0246 (15)	−0.0245 (12)	−0.0295 (13)
O4	0.0801 (14)	0.0611 (12)	0.0717 (13)	0.0223 (10)	−0.0274 (11)	−0.0086 (10)
O5	0.0854 (14)	0.0464 (10)	0.0574 (11)	0.0139 (9)	−0.0089 (10)	−0.0088 (8)
C1	0.0521 (14)	0.0522 (14)	0.0548 (15)	0.0049 (11)	−0.0040 (11)	−0.0055 (11)
C2	0.0565 (16)	0.0618 (17)	0.079 (2)	0.0149 (13)	−0.0071 (14)	−0.0196 (15)
C3	0.0469 (14)	0.082 (2)	0.074 (2)	0.0115 (14)	−0.0081 (13)	−0.0328 (16)
C4	0.0463 (14)	0.086 (2)	0.0519 (15)	0.0026 (13)	−0.0039 (11)	−0.0169 (14)
C5	0.0486 (13)	0.0611 (16)	0.0507 (14)	0.0012 (11)	−0.0027 (11)	−0.0016 (12)
C6	0.0470 (13)	0.0502 (13)	0.0475 (13)	0.0026 (10)	−0.0004 (10)	−0.0019 (10)
C7	0.0531 (13)	0.0499 (13)	0.0489 (14)	0.0059 (11)	−0.0046 (11)	0.0015 (11)
C8	0.0505 (13)	0.0427 (12)	0.0428 (12)	0.0081 (9)	−0.0004 (10)	0.0035 (9)
C9	0.0772 (19)	0.0505 (15)	0.0539 (15)	0.0214 (13)	−0.0103 (13)	−0.0073 (12)
C10	0.0558 (13)	0.0411 (12)	0.0442 (12)	0.0091 (10)	0.0021 (10)	0.0011 (10)
C11	0.0591 (14)	0.0456 (13)	0.0439 (12)	0.0107 (10)	0.0030 (10)	−0.0007 (10)
C12	0.0576 (14)	0.0609 (16)	0.0463 (13)	0.0153 (12)	−0.0054 (11)	−0.0012 (11)
C13	0.0508 (13)	0.0638 (16)	0.0443 (13)	0.0043 (11)	−0.0065 (10)	0.0031 (11)
C14	0.0613 (16)	0.084 (2)	0.0623 (17)	0.0040 (15)	0.0077 (13)	0.0281 (16)
C15	0.098 (3)	0.068 (2)	0.097 (3)	−0.0018 (18)	0.012 (2)	0.0305 (19)
C16	0.091 (2)	0.121 (3)	0.062 (2)	0.020 (2)	0.0053 (17)	0.041 (2)
C17	0.0583 (15)	0.0672 (17)	0.0459 (13)	0.0158 (12)	−0.0051 (11)	−0.0047 (12)
C18	0.087 (2)	0.0519 (16)	0.0684 (19)	0.0094 (14)	−0.0002 (16)	−0.0034 (13)
C19	0.082 (2)	0.109 (3)	0.0609 (19)	0.039 (2)	0.0036 (16)	−0.0053 (18)
C20	0.116 (3)	0.097 (3)	0.119 (4)	0.025 (3)	0.009 (3)	−0.050 (3)
C21	0.082 (2)	0.120 (3)	0.063 (2)	0.021 (2)	−0.0207 (17)	−0.006 (2)
S2A	0.1503 (19)	0.0728 (10)	0.158 (2)	−0.0025 (10)	0.0901 (17)	−0.0074 (11)
O6A	0.197 (11)	0.065 (4)	0.099 (7)	0.020 (5)	0.014 (5)	−0.007 (4)
C22A	0.28 (3)	0.128 (15)	0.30 (3)	0.103 (17)	0.16 (3)	0.068 (17)
C23A	0.166 (14)	0.224 (16)	0.269 (19)	−0.004 (13)	−0.037 (14)	−0.180 (15)
S2B	0.109 (3)	0.0695 (17)	0.161 (4)	−0.0073 (16)	0.065 (3)	0.0062 (19)
O6B	0.113 (8)	0.048 (6)	0.127 (17)	0.001 (5)	0.021 (10)	0.000 (8)
C22B	0.149 (16)	0.057 (9)	0.157 (18)	0.021 (9)	0.067 (14)	0.049 (10)
C23B	0.097 (12)	0.21 (2)	0.116 (13)	−0.065 (14)	0.028 (10)	−0.048 (14)

Geometric parameters (Å, º)

S1—C9	1.718 (3)	C1—C2	1.399 (4)
S1—C8	1.727 (3)	C2—C3	1.379 (5)
N1—C7	1.364 (3)	C3—C4	1.388 (5)
N1—C8	1.383 (3)	C4—C5	1.377 (4)
N2—C8	1.296 (3)	C5—C6	1.410 (4)
N2—C10	1.382 (3)	C6—C7	1.487 (4)
N3—C11	1.336 (4)	C9—C10	1.335 (4)
N3—C12	1.446 (3)	C10—C11	1.492 (3)
N4—C13	1.511 (3)	C12—C13	1.509 (4)
N4—C17	1.520 (4)	C14—C15	1.514 (5)
N4—C14	1.525 (4)	C14—C16	1.519 (5)
O1—C1	1.365 (3)	C17—C18	1.506 (4)
O2—C20	1.276 (5)	C17—C19	1.518 (4)
O2—C3	1.357 (4)	S2A—O6A	1.435 (16)
O3—C4	1.370 (4)	S2A—C23A	1.705 (16)
O3—C21	1.400 (5)	S2A—C22A	1.81 (3)
O4—C7	1.219 (3)	S2B—O6B	1.47 (2)
O5—C11	1.225 (3)	S2B—C22B	1.75 (3)
C1—C6	1.386 (4)	S2B—C23B	1.802 (16)
C9—S1—C8	88.15 (13)	N1—C7—C6	117.2 (2)
C7—N1—C8	124.4 (2)	N2—C8—N1	120.8 (2)
C8—N2—C10	109.5 (2)	N2—C8—S1	115.78 (18)
C11—N3—C12	121.7 (2)	N1—C8—S1	123.43 (19)
C13—N4—C17	112.3 (2)	C10—C9—S1	110.7 (2)
C13—N4—C14	111.1 (2)	C9—C10—N2	115.8 (2)
C17—N4—C14	115.4 (2)	C9—C10—C11	123.6 (2)
C20—O2—C3	122.4 (3)	N2—C10—C11	120.5 (2)
C4—O3—C21	118.3 (3)	O5—C11—N3	123.8 (2)
O1—C1—C6	119.9 (2)	O5—C11—C10	121.5 (2)
O1—C1—C2	120.2 (3)	N3—C11—C10	114.7 (2)
C6—C1—C2	119.8 (3)	N3—C12—C13	110.4 (2)
C3—C2—C1	120.8 (3)	C12—C13—N4	111.6 (2)
O2—C3—C2	123.9 (4)	C15—C14—C16	110.5 (3)
O2—C3—C4	116.0 (3)	C15—C14—N4	109.5 (3)
C2—C3—C4	120.1 (3)	C16—C14—N4	111.8 (3)
O3—C4—C5	125.1 (3)	C18—C17—C19	113.7 (3)
O3—C4—C3	115.6 (3)	C18—C17—N4	109.9 (2)
C5—C4—C3	119.2 (3)	C19—C17—N4	111.6 (3)
C4—C5—C6	121.7 (3)	O6A—S2A—C23A	110.0 (9)
C1—C6—C5	118.4 (2)	O6A—S2A—C22A	108.0 (12)
C1—C6—C7	125.9 (2)	C23A—S2A—C22A	97.9 (12)
C5—C6—C7	115.7 (2)	O6B—S2B—C22B	101.8 (17)
O4—C7—N1	120.8 (2)	O6B—S2B—C23B	113.3 (15)
O4—C7—C6	122.0 (2)	C22B—S2B—C23B	98.6 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O1	0.86 (3)	1.93 (3)	2.644 (3)	140 (3)
N3—H3A···O6A^i	0.80 (4)	2.26 (4)	2.899 (18)	138 (3)
N4—H4A···Cl1^ii	0.83 (3)	2.36 (3)	3.183 (2)	172 (3)
O1—H1A···Cl1^iii	0.90 (4)	2.09 (4)	2.982 (2)	177 (4)

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

(1AH-1DMSO-II)

Crystal data

C21H31N4O5S·Cl·C2H6OS·	Z = 2
Mr = 565.13	F(000) = 600
Triclinic, P1	Dx = 1.294 Mg m^−3
a = 10.4385 (11) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.7052 (11) Å	Cell parameters from 7189 reflections
c = 14.2725 (14) Å	θ = 2.6–28.4°
α = 90.444 (2)°	µ = 0.32 mm^−1
β = 95.087 (3)°	T = 293 K
γ = 113.920 (2)°	Prism, colorless
V = 1450.5 (3) Å^3	0.15 × 0.08 × 0.06 mm

Data collection

CCD diffractometer	4971 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.030
ωκ scans	θmax = 28.4°, θmin = 2.6°
Absorption correction: multi-scan Higashi, T. (1995)	h = −13→13
Tmin = 0.970, Tmax = 0.981	k = −14→14
21353 measured reflections	l = −18→19
7189 independent reflections

Refinement

Refinement on F^2	6 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.056	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.166	w = 1/[σ^2(Fo^2) + (0.079P)^2 + 0.4075P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
7189 reflections	Δρmax = 0.44 e Å^−3
358 parameters	Δρmin = −0.35 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	0.73699 (7)	0.88988 (6)	0.47417 (4)	0.05998 (17)
S2	0.94268 (12)	0.67478 (9)	0.08052 (7)	0.1131 (4)
Cl1	1.30502 (6)	1.07829 (6)	0.08750 (4)	0.06813 (19)
O1	1.1367 (2)	1.09573 (15)	0.24090 (16)	0.0812 (6)
O2	1.3642 (2)	1.58040 (16)	0.21136 (14)	0.0858 (6)
O3	1.2398 (2)	1.62614 (15)	0.34722 (14)	0.0893 (6)
O4	0.90348 (19)	1.15934 (16)	0.44138 (12)	0.0707 (4)
O5	0.6002 (2)	0.43103 (18)	0.41856 (15)	0.1014 (7)
O6	0.8206 (4)	0.5612 (2)	0.1146 (2)	0.1578 (14)
N1	0.9479 (2)	1.00479 (17)	0.35926 (15)	0.0580 (5)
N2	0.8258 (2)	0.76888 (17)	0.35647 (13)	0.0622 (5)
N3A	0.7709 (3)	0.4950 (3)	0.3197 (2)	0.0602 (9)	0.645 (4)
H3A	0.824 (3)	0.557 (3)	0.294 (2)	0.049 (9)*	0.645 (4)
N3B	0.6760 (5)	0.5056 (5)	0.2741 (3)	0.0504 (13)*	0.355 (4)
H3B	0.746 (5)	0.553 (6)	0.247 (4)	0.061 (18)*	0.355 (4)
N4	0.5993 (2)	0.14679 (16)	0.19554 (12)	0.0532 (4)
C1	1.1581 (2)	1.22580 (19)	0.26862 (16)	0.0551 (5)
C2	1.2516 (2)	1.3356 (2)	0.22457 (17)	0.0610 (6)
H2B	1.2985	1.3200	0.1764	0.073*
C3	1.2757 (3)	1.4679 (2)	0.25168 (18)	0.0634 (6)
C4	1.2059 (3)	1.4909 (2)	0.32503 (17)	0.0629 (6)
C5	1.1119 (2)	1.3820 (2)	0.36630 (15)	0.0575 (5)
H5A	1.0643	1.3979	0.4139	0.069*
C6	1.0845 (2)	1.24571 (19)	0.33898 (14)	0.0498 (4)
C7	0.9738 (2)	1.1364 (2)	0.38507 (14)	0.0517 (5)
C8	0.8456 (2)	0.8886 (2)	0.39011 (14)	0.0501 (4)
C9	0.6606 (3)	0.7148 (2)	0.46344 (15)	0.0598 (5)
H9A	0.5879	0.6591	0.4971	0.072*
C10	0.7203 (2)	0.6699 (2)	0.39991 (15)	0.0598 (5)
C11	0.6816 (4)	0.5226 (2)	0.3763 (2)	0.0956 (11)
C12A	0.7551 (4)	0.3581 (3)	0.2934 (2)	0.0566 (9)	0.645 (4)
H12A	0.7468	0.3048	0.3489	0.068*	0.645 (4)
H12B	0.8372	0.3623	0.2642	0.068*	0.645 (4)
C12B	0.6079 (6)	0.3695 (6)	0.2287 (4)	0.0482 (14)*	0.355 (4)
H12C	0.5903	0.3771	0.1616	0.058*	0.355 (4)
H12D	0.5178	0.3208	0.2531	0.058*	0.355 (4)
C13A	0.6252 (4)	0.2920 (3)	0.2254 (2)	0.0469 (8)	0.645 (4)
H13A	0.6350	0.3459	0.1701	0.056*	0.645 (4)
H13B	0.5444	0.2910	0.2547	0.056*	0.645 (4)
C13B	0.6973 (7)	0.2894 (6)	0.2451 (4)	0.0417 (13)*	0.355 (4)
H13C	0.7183	0.2813	0.3118	0.050*	0.355 (4)
H13D	0.7847	0.3310	0.2163	0.050*	0.355 (4)
C14	0.5843 (3)	0.0481 (2)	0.27433 (15)	0.0587 (5)
H14A	0.6773	0.0722	0.3087	0.070*
C15	0.5308 (3)	−0.0984 (2)	0.2345 (2)	0.0831 (8)
H15A	0.5941	−0.1049	0.1917	0.125*
H15B	0.5258	−0.1584	0.2850	0.125*
H15C	0.4388	−0.1244	0.2016	0.125*
C16	0.4873 (3)	0.0623 (3)	0.34202 (19)	0.0794 (7)
H16A	0.5231	0.1554	0.3662	0.119*
H16B	0.3950	0.0372	0.3098	0.119*
H16C	0.4821	0.0032	0.3932	0.119*
C17	0.6755 (2)	0.1271 (2)	0.11372 (15)	0.0596 (5)
H17A	0.6224	0.0329	0.0884	0.072*
C18	0.6700 (3)	0.2191 (3)	0.03581 (17)	0.0747 (7)
H18A	0.5742	0.2063	0.0193	0.112*
H18B	0.7254	0.3127	0.0566	0.112*
H18C	0.7070	0.1971	−0.0182	0.112*
C19	0.8230 (3)	0.1414 (4)	0.1436 (2)	0.0964 (10)
H19A	0.8210	0.0809	0.1933	0.145*
H19B	0.8618	0.1185	0.0910	0.145*
H19C	0.8803	0.2341	0.1658	0.145*
C20	1.4347 (4)	1.5612 (3)	0.1353 (3)	0.1170 (13)
H20A	1.4935	1.6486	0.1135	0.175*
H20B	1.4917	1.5134	0.1562	0.175*
H20C	1.3664	1.5085	0.0848	0.175*
C21	1.1710 (4)	1.6557 (3)	0.4206 (2)	0.1074 (12)
H21A	1.2030	1.7530	0.4297	0.161*
H21B	1.0710	1.6156	0.4037	0.161*
H21C	1.1925	1.6185	0.4778	0.161*
C22	1.0784 (4)	0.7289 (5)	0.1752 (3)	0.1460 (18)
H22A	1.1599	0.8028	0.1561	0.219*
H22B	1.0463	0.7594	0.2282	0.219*
H22C	1.1023	0.6539	0.1923	0.219*
C23	0.9061 (4)	0.8174 (4)	0.0907 (3)	0.1282 (14)
H23A	0.9817	0.8953	0.0696	0.192*
H23B	0.8200	0.8025	0.0528	0.192*
H23C	0.8963	0.8337	0.1554	0.192*
H4A	0.505 (3)	0.119 (3)	0.1698 (19)	0.083 (9)*
H1A	1.178 (3)	1.097 (3)	0.2050 (19)	0.065 (8)*
H1B	0.995 (3)	0.993 (3)	0.325 (2)	0.075 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0823 (4)	0.0546 (3)	0.0519 (3)	0.0351 (3)	0.0172 (3)	−0.0023 (2)
S2	0.1441 (8)	0.0745 (5)	0.1053 (6)	0.0186 (5)	0.0626 (6)	0.0098 (4)
Cl1	0.0686 (4)	0.0674 (4)	0.0707 (4)	0.0301 (3)	0.0086 (3)	−0.0144 (3)
O1	0.0792 (12)	0.0349 (7)	0.1268 (16)	0.0129 (7)	0.0502 (12)	−0.0180 (8)
O2	0.1097 (14)	0.0377 (8)	0.1060 (14)	0.0202 (9)	0.0401 (12)	−0.0021 (8)
O3	0.1417 (17)	0.0370 (8)	0.0915 (12)	0.0340 (9)	0.0363 (12)	−0.0093 (8)
O4	0.0957 (12)	0.0526 (8)	0.0701 (10)	0.0334 (8)	0.0260 (9)	−0.0077 (7)
O5	0.1336 (18)	0.0514 (9)	0.0980 (14)	0.0050 (10)	0.0664 (13)	−0.0042 (9)
O6	0.193 (3)	0.0665 (14)	0.156 (2)	−0.0204 (16)	0.089 (2)	−0.0072 (14)
N1	0.0550 (10)	0.0390 (8)	0.0755 (12)	0.0130 (8)	0.0153 (9)	−0.0151 (8)
N2	0.0667 (11)	0.0399 (8)	0.0689 (11)	0.0074 (8)	0.0229 (9)	−0.0159 (8)
N3A	0.069 (2)	0.0315 (13)	0.0696 (19)	0.0065 (12)	0.0257 (16)	−0.0098 (12)
N4	0.0689 (12)	0.0337 (8)	0.0513 (9)	0.0143 (8)	0.0104 (8)	−0.0068 (7)
C1	0.0485 (11)	0.0350 (9)	0.0796 (14)	0.0157 (8)	0.0033 (10)	−0.0171 (9)
C2	0.0576 (12)	0.0389 (10)	0.0839 (15)	0.0162 (9)	0.0127 (11)	−0.0143 (10)
C3	0.0715 (14)	0.0368 (10)	0.0801 (15)	0.0200 (10)	0.0082 (12)	−0.0077 (10)
C4	0.0853 (16)	0.0355 (10)	0.0678 (13)	0.0253 (10)	0.0052 (11)	−0.0114 (9)
C5	0.0776 (15)	0.0428 (10)	0.0548 (11)	0.0284 (10)	0.0030 (10)	−0.0131 (9)
C6	0.0506 (11)	0.0386 (9)	0.0590 (11)	0.0193 (8)	−0.0047 (9)	−0.0138 (8)
C7	0.0588 (12)	0.0427 (10)	0.0545 (11)	0.0238 (9)	−0.0047 (9)	−0.0136 (8)
C8	0.0532 (11)	0.0434 (10)	0.0508 (10)	0.0172 (9)	0.0034 (8)	−0.0111 (8)
C9	0.0735 (14)	0.0537 (12)	0.0513 (11)	0.0233 (11)	0.0156 (10)	0.0005 (9)
C10	0.0680 (13)	0.0459 (11)	0.0551 (12)	0.0110 (10)	0.0158 (10)	−0.0089 (9)
C11	0.123 (2)	0.0471 (13)	0.0878 (18)	−0.0044 (14)	0.0592 (18)	−0.0182 (12)
C12A	0.0559 (19)	0.0392 (15)	0.067 (2)	0.0121 (14)	0.0036 (15)	−0.0167 (14)
C13A	0.057 (2)	0.0371 (15)	0.0523 (17)	0.0243 (14)	0.0077 (15)	−0.0023 (12)
C14	0.0702 (14)	0.0401 (10)	0.0561 (12)	0.0140 (10)	−0.0014 (10)	−0.0003 (8)
C15	0.111 (2)	0.0388 (11)	0.0845 (17)	0.0201 (13)	−0.0126 (16)	−0.0041 (11)
C16	0.0939 (19)	0.0676 (15)	0.0677 (15)	0.0209 (14)	0.0211 (14)	0.0152 (12)
C17	0.0638 (13)	0.0584 (12)	0.0523 (11)	0.0209 (10)	0.0050 (10)	−0.0186 (9)
C18	0.0908 (18)	0.0695 (15)	0.0579 (13)	0.0234 (14)	0.0242 (12)	−0.0040 (11)
C19	0.0738 (18)	0.135 (3)	0.0828 (18)	0.0467 (18)	0.0020 (14)	−0.0301 (18)
C20	0.142 (3)	0.0545 (16)	0.148 (3)	0.0214 (18)	0.076 (3)	0.0001 (17)
C21	0.187 (4)	0.0521 (14)	0.093 (2)	0.0525 (19)	0.048 (2)	−0.0094 (13)
C22	0.119 (3)	0.175 (5)	0.160 (4)	0.071 (3)	0.032 (3)	0.077 (4)
C23	0.104 (3)	0.099 (3)	0.162 (4)	0.027 (2)	−0.021 (3)	0.004 (2)

Geometric parameters (Å, º)

S1—C9	1.713 (2)	C12A—C13A	1.503 (5)
S1—C8	1.725 (2)	C12A—H12A	0.9700
S2—O6	1.483 (2)	C12A—H12B	0.9700
S2—C23	1.725 (4)	C12B—C13B	1.508 (8)
S2—C22	1.775 (4)	C12B—H12C	0.9700
O1—C1	1.367 (2)	C12B—H12D	0.9700
O1—H1A	0.69 (3)	C13A—H13A	0.9700
O2—C3	1.356 (3)	C13A—H13B	0.9700
O2—C20	1.423 (4)	C13B—H13C	0.9700
O3—C4	1.371 (2)	C13B—H13D	0.9700
O3—C21	1.423 (3)	C14—C16	1.509 (4)
O4—C7	1.222 (2)	C14—C15	1.522 (3)
O5—C11	1.213 (3)	C14—H14A	0.9800
N1—C7	1.364 (2)	C15—H15A	0.9600
N1—C8	1.377 (3)	C15—H15B	0.9600
N1—H1B	0.77 (3)	C15—H15C	0.9600
N2—C8	1.294 (2)	C16—H16A	0.9600
N2—C10	1.381 (3)	C16—H16B	0.9600
N3A—C11	1.400 (4)	C16—H16C	0.9600
N3A—C12A	1.449 (4)	C17—C18	1.504 (3)
N3A—H3A	0.791 (18)	C17—C19	1.505 (4)
N3B—C12B	1.453 (7)	C17—H17A	0.9800
N3B—C11	1.461 (6)	C18—H18A	0.9600
N3B—H3B	0.83 (2)	C18—H18B	0.9600
N4—C13A	1.517 (3)	C18—H18C	0.9600
N4—C14	1.523 (3)	C19—H19A	0.9600
N4—C17	1.529 (3)	C19—H19B	0.9600
N4—C13B	1.570 (6)	C19—H19C	0.9600
N4—H4A	0.94 (3)	C20—H20A	0.9600
C1—C6	1.382 (3)	C20—H20B	0.9600
C1—C2	1.386 (3)	C20—H20C	0.9600
C2—C3	1.380 (3)	C21—H21A	0.9600
C2—H2B	0.9300	C21—H21B	0.9600
C3—C4	1.402 (3)	C21—H21C	0.9600
C4—C5	1.361 (3)	C22—H22A	0.9600
C5—C6	1.413 (2)	C22—H22B	0.9600
C5—H5A	0.9300	C22—H22C	0.9600
C6—C7	1.479 (3)	C23—H23A	0.9600
C9—C10	1.334 (3)	C23—H23B	0.9600
C9—H9A	0.9300	C23—H23C	0.9600
C10—C11	1.488 (3)
C9—S1—C8	88.54 (10)	C12A—C13A—N4	112.2 (3)
O6—S2—C23	105.2 (2)	C12A—C13A—H13A	109.2
O6—S2—C22	106.6 (2)	N4—C13A—H13A	109.2
C23—S2—C22	94.4 (2)	C12A—C13A—H13B	109.2
C1—O1—H1A	111 (2)	N4—C13A—H13B	109.2
C3—O2—C20	118.14 (18)	H13A—C13A—H13B	107.9
C4—O3—C21	117.0 (2)	C12B—C13B—N4	101.9 (4)
C7—N1—C8	126.20 (19)	C12B—C13B—H13C	111.4
C7—N1—H1B	118 (2)	N4—C13B—H13C	111.4
C8—N1—H1B	116 (2)	C12B—C13B—H13D	111.4
C8—N2—C10	109.41 (17)	N4—C13B—H13D	111.4
C11—N3A—C12A	123.7 (3)	H13C—C13B—H13D	109.3
C11—N3A—H3A	117 (3)	C16—C14—C15	111.0 (2)
C12A—N3A—H3A	118 (3)	C16—C14—N4	109.90 (19)
C12B—N3B—C11	119.7 (4)	C15—C14—N4	110.80 (18)
C12B—N3B—H3B	110 (5)	C16—C14—H14A	108.4
C11—N3B—H3B	119 (5)	C15—C14—H14A	108.4
C13A—N4—C14	116.24 (18)	N4—C14—H14A	108.4
C13A—N4—C17	117.68 (18)	C14—C15—H15A	109.5
C14—N4—C17	115.18 (17)	C14—C15—H15B	109.5
C14—N4—C13B	103.1 (2)	H15A—C15—H15B	109.5
C17—N4—C13B	106.2 (3)	C14—C15—H15C	109.5
C13A—N4—H4A	97.4 (17)	H15A—C15—H15C	109.5
C14—N4—H4A	101.7 (17)	H15B—C15—H15C	109.5
C17—N4—H4A	104.3 (17)	C14—C16—H16A	109.5
C13B—N4—H4A	126.9 (17)	C14—C16—H16B	109.5
O1—C1—C6	119.57 (19)	H16A—C16—H16B	109.5
O1—C1—C2	119.40 (19)	C14—C16—H16C	109.5
C6—C1—C2	121.03 (17)	H16A—C16—H16C	109.5
C3—C2—C1	120.5 (2)	H16B—C16—H16C	109.5
C3—C2—H2B	119.8	C18—C17—C19	112.6 (2)
C1—C2—H2B	119.8	C18—C17—N4	110.40 (18)
O2—C3—C2	124.0 (2)	C19—C17—N4	113.20 (19)
O2—C3—C4	116.44 (18)	C18—C17—H17A	106.7
C2—C3—C4	119.6 (2)	C19—C17—H17A	106.7
C5—C4—O3	126.1 (2)	N4—C17—H17A	106.7
C5—C4—C3	119.35 (18)	C17—C18—H18A	109.5
O3—C4—C3	114.5 (2)	C17—C18—H18B	109.5
C4—C5—C6	122.0 (2)	H18A—C18—H18B	109.5
C4—C5—H5A	119.0	C17—C18—H18C	109.5
C6—C5—H5A	119.0	H18A—C18—H18C	109.5
C1—C6—C5	117.50 (19)	H18B—C18—H18C	109.5
C1—C6—C7	125.61 (16)	C17—C19—H19A	109.5
C5—C6—C7	116.82 (18)	C17—C19—H19B	109.5
O4—C7—N1	119.9 (2)	H19A—C19—H19B	109.5
O4—C7—C6	123.14 (17)	C17—C19—H19C	109.5
N1—C7—C6	116.88 (18)	H19A—C19—H19C	109.5
N2—C8—N1	120.56 (18)	H19B—C19—H19C	109.5
N2—C8—S1	115.51 (16)	O2—C20—H20A	109.5
N1—C8—S1	123.92 (14)	O2—C20—H20B	109.5
C10—C9—S1	110.29 (17)	H20A—C20—H20B	109.5
C10—C9—H9A	124.9	O2—C20—H20C	109.5
S1—C9—H9A	124.9	H20A—C20—H20C	109.5
C9—C10—N2	116.22 (19)	H20B—C20—H20C	109.5
C9—C10—C11	123.9 (2)	O3—C21—H21A	109.5
N2—C10—C11	119.87 (19)	O3—C21—H21B	109.5
O5—C11—N3A	119.5 (3)	H21A—C21—H21B	109.5
O5—C11—N3B	118.8 (3)	O3—C21—H21C	109.5
O5—C11—C10	123.0 (2)	H21A—C21—H21C	109.5
N3A—C11—C10	115.5 (2)	H21B—C21—H21C	109.5
N3B—C11—C10	107.7 (3)	S2—C22—H22A	109.5
N3A—C12A—C13A	108.7 (3)	S2—C22—H22B	109.5
N3A—C12A—H12A	109.9	H22A—C22—H22B	109.5
C13A—C12A—H12A	109.9	S2—C22—H22C	109.5
N3A—C12A—H12B	109.9	H22A—C22—H22C	109.5
C13A—C12A—H12B	109.9	H22B—C22—H22C	109.5
H12A—C12A—H12B	108.3	S2—C23—H23A	109.5
N3B—C12B—C13B	111.5 (5)	S2—C23—H23B	109.5
N3B—C12B—H12C	109.3	H23A—C23—H23B	109.5
C13B—C12B—H12C	109.3	S2—C23—H23C	109.5
N3B—C12B—H12D	109.3	H23A—C23—H23C	109.5
C13B—C12B—H12D	109.3	H23B—C23—H23C	109.5
H12C—C12B—H12D	108.0
O1—C1—C2—C3	−179.6 (2)	S1—C9—C10—C11	177.8 (2)
C6—C1—C2—C3	1.5 (4)	C8—N2—C10—C9	1.2 (3)
C20—O2—C3—C2	1.2 (4)	C8—N2—C10—C11	−177.4 (2)
C20—O2—C3—C4	−178.6 (3)	C12A—N3A—C11—O5	12.2 (6)
C1—C2—C3—O2	−179.2 (2)	C12A—N3A—C11—C10	176.6 (3)
C1—C2—C3—C4	0.7 (4)	C12B—N3B—C11—O5	−19.0 (7)
C21—O3—C4—C5	0.3 (4)	C12B—N3B—C11—C10	−164.8 (4)
C21—O3—C4—C3	179.4 (3)	C9—C10—C11—O5	−6.1 (5)
O2—C3—C4—C5	177.8 (2)	N2—C10—C11—O5	172.4 (3)
C2—C3—C4—C5	−2.1 (4)	C9—C10—C11—N3A	−169.9 (3)
O2—C3—C4—O3	−1.3 (3)	N2—C10—C11—N3A	8.6 (4)
C2—C3—C4—O3	178.8 (2)	C9—C10—C11—N3B	138.1 (3)
O3—C4—C5—C6	−179.6 (2)	N2—C10—C11—N3B	−43.5 (4)
C3—C4—C5—C6	1.5 (4)	C11—N3A—C12A—C13A	70.1 (4)
O1—C1—C6—C5	179.0 (2)	C11—N3B—C12B—C13B	−74.3 (6)
C2—C1—C6—C5	−2.1 (3)	N3A—C12A—C13A—N4	−179.0 (2)
O1—C1—C6—C7	−4.4 (3)	C14—N4—C13A—C12A	57.7 (3)
C2—C1—C6—C7	174.6 (2)	C17—N4—C13A—C12A	−84.9 (3)
C4—C5—C6—C1	0.6 (3)	N3B—C12B—C13B—N4	176.8 (4)
C4—C5—C6—C7	−176.3 (2)	C14—N4—C13B—C12B	−122.6 (3)
C8—N1—C7—O4	0.7 (3)	C17—N4—C13B—C12B	115.9 (4)
C8—N1—C7—C6	−176.80 (19)	C13A—N4—C14—C16	45.9 (3)
C1—C6—C7—O4	−173.7 (2)	C17—N4—C14—C16	−170.59 (19)
C5—C6—C7—O4	3.0 (3)	C13B—N4—C14—C16	74.2 (3)
C1—C6—C7—N1	3.8 (3)	C13A—N4—C14—C15	168.9 (2)
C5—C6—C7—N1	−179.55 (18)	C17—N4—C14—C15	−47.6 (3)
C10—N2—C8—N1	178.7 (2)	C13B—N4—C14—C15	−162.8 (3)
C10—N2—C8—S1	−1.1 (3)	C13A—N4—C17—C18	−43.3 (3)
C7—N1—C8—N2	176.1 (2)	C14—N4—C17—C18	173.77 (19)
C7—N1—C8—S1	−4.2 (3)	C13B—N4—C17—C18	−72.8 (3)
C9—S1—C8—N2	0.60 (18)	C13A—N4—C17—C19	84.0 (3)
C9—S1—C8—N1	−179.2 (2)	C14—N4—C17—C19	−58.9 (3)
C8—S1—C9—C10	0.10 (19)	C13B—N4—C17—C19	54.4 (3)
S1—C9—C10—N2	−0.8 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O1	0.77 (3)	1.97 (3)	2.597 (3)	139 (3)
O1—H1A···Cl1	0.69 (3)	2.28 (3)	2.976 (2)	174 (3)
N4—H4A···Cl1^i	0.94 (3)	2.18 (3)	3.110 (2)	169 (2)
N3B—H3B···O6	0.83 (2)	2.10 (5)	2.779 (6)	139 (6)

Symmetry code: (i) x−1, y−1, z.

(1AH-1W-1DMSO)

Crystal data

C21H31N4O5S·Cl·C2H6OS·H2O	F(000) = 1240
Mr = 583.15	Dx = 1.318 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 16.508 (1) Å	Cell parameters from 43045 reflections
b = 11.873 (1) Å	θ = 3.1–28.3°
c = 15.442 (1) Å	µ = 0.32 mm^−1
β = 103.917 (1)°	T = 293 K
V = 2937.8 (4) Å^3	Prism, colorless
Z = 4	0.17 × 0.16 × 0.10 mm

Data collection

CCD diffractometer	4861 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.042
ωκ scans	θmax = 28.3°, θmin = 3.1°
Absorption correction: multi-scan Higashi, T. (1995)	h = −22→22
Tmin = 0.947, Tmax = 0.969	k = −15→15
43045 measured reflections	l = −20→19
7301 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.047	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.128	w = 1/[σ^2(Fo^2) + (0.058P)^2 + 0.9498P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.001
7301 reflections	Δρmax = 0.35 e Å^−3
366 parameters	Δρmin = −0.49 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.42024 (3)	0.71529 (4)	0.13397 (4)	0.04562 (14)
S2	0.17409 (4)	0.23400 (8)	0.45542 (5)	0.0827 (2)
Cl1	0.12427 (4)	0.95621 (4)	0.27744 (4)	0.05987 (17)
O1	0.60201 (10)	1.05821 (15)	0.08602 (13)	0.0637 (5)
O2	0.52288 (10)	1.43652 (12)	0.12770 (11)	0.0609 (4)
O3	0.39320 (9)	1.37170 (11)	0.17924 (11)	0.0543 (4)
O4	0.50594 (8)	0.90123 (12)	0.11671 (10)	0.0528 (4)
O5	0.18422 (10)	0.53685 (12)	0.16686 (14)	0.0716 (5)
O6	0.24948 (12)	0.07324 (17)	0.1800 (2)	0.0765 (6)
O7	0.16908 (14)	0.29451 (19)	0.53751 (15)	0.0969 (7)
N1	0.38384 (10)	0.93902 (14)	0.15024 (12)	0.0415 (4)
N2	0.28768 (9)	0.80257 (12)	0.16600 (10)	0.0387 (4)
N3	0.14177 (11)	0.71185 (15)	0.18830 (11)	0.0429 (4)
N4	0.06935 (9)	0.73208 (13)	0.35682 (10)	0.0341 (3)
C1	0.54662 (12)	1.13020 (17)	0.10839 (14)	0.0449 (5)
C2	0.56380 (12)	1.24463 (18)	0.10589 (14)	0.0494 (5)
H2A	0.6114	1.2681	0.0888	0.059*
C3	0.51149 (12)	1.32331 (17)	0.12826 (13)	0.0440 (5)
C4	0.44019 (12)	1.28799 (16)	0.15514 (13)	0.0415 (4)
C5	0.42260 (11)	1.17558 (16)	0.15644 (13)	0.0405 (4)
H5A	0.3748	1.1527	0.1734	0.049*
C6	0.47502 (11)	1.09352 (16)	0.13268 (13)	0.0387 (4)
C7	0.45710 (11)	0.97301 (16)	0.13266 (13)	0.0402 (4)
C8	0.35988 (11)	0.82816 (15)	0.15154 (12)	0.0365 (4)
C9	0.34212 (13)	0.62811 (17)	0.14656 (15)	0.0487 (5)
H9A	0.3438	0.5500	0.1430	0.058*
C10	0.27753 (12)	0.68708 (15)	0.16243 (13)	0.0401 (4)
C11	0.19812 (13)	0.63803 (16)	0.17336 (14)	0.0444 (5)
C12	0.05985 (12)	0.67711 (18)	0.19673 (13)	0.0454 (5)
H12A	0.0402	0.6164	0.1549	0.054*
H12B	0.0216	0.7398	0.1802	0.054*
C13	0.05763 (12)	0.63809 (16)	0.28916 (13)	0.0403 (4)
H13A	0.1011	0.5824	0.3090	0.048*
H13B	0.0045	0.6017	0.2864	0.048*
C14	−0.01321 (12)	0.77004 (17)	0.37589 (13)	0.0431 (4)
H14A	−0.0359	0.7077	0.4043	0.052*
C15	−0.07543 (13)	0.8002 (2)	0.29018 (16)	0.0616 (6)
H15A	−0.0883	0.7343	0.2533	0.092*
H15B	−0.0520	0.8569	0.2591	0.092*
H15C	−0.1255	0.8284	0.3036	0.092*
C16	0.00154 (15)	0.8696 (2)	0.43934 (16)	0.0596 (6)
H16A	0.0318	0.8451	0.4974	0.089*
H16B	−0.0511	0.9007	0.4433	0.089*
H16C	0.0333	0.9260	0.4175	0.089*
C17	0.13550 (13)	0.70424 (19)	0.44152 (13)	0.0485 (5)
H17A	0.1386	0.7687	0.4818	0.058*
C18	0.22012 (13)	0.6941 (3)	0.41974 (17)	0.0696 (7)
H18A	0.2286	0.7573	0.3842	0.104*
H18B	0.2222	0.6257	0.3872	0.104*
H18C	0.2631	0.6928	0.4741	0.104*
C19	0.11229 (18)	0.6031 (2)	0.48913 (17)	0.0757 (8)
H19A	0.0609	0.6177	0.5058	0.114*
H19B	0.1556	0.5884	0.5417	0.114*
H19C	0.1056	0.5389	0.4503	0.114*
C20	0.59733 (18)	1.4769 (2)	0.1065 (2)	0.0833 (9)
H20A	0.5995	1.5575	0.1117	0.125*
H20B	0.5974	1.4556	0.0466	0.125*
H20C	0.6451	1.4448	0.1471	0.125*
C21	0.33448 (14)	1.33864 (19)	0.22863 (17)	0.0563 (6)
H21A	0.3109	1.4045	0.2490	0.085*
H21B	0.3621	1.2942	0.2790	0.085*
H21C	0.2909	1.2950	0.1911	0.085*
C22	0.2536 (3)	0.2996 (5)	0.4143 (3)	0.157 (2)
H22A	0.2674	0.2530	0.3690	0.236*
H22B	0.3023	0.3098	0.4622	0.236*
H22C	0.2344	0.3716	0.3892	0.236*
C23	0.2270 (2)	0.1070 (3)	0.4888 (2)	0.1019 (11)
H23A	0.2305	0.0643	0.4370	0.153*
H23B	0.1973	0.0643	0.5240	0.153*
H23C	0.2823	0.1230	0.5237	0.153*
H4A	0.0876 (12)	0.7914 (17)	0.3336 (13)	0.038 (5)*
H3A	0.1527 (14)	0.779 (2)	0.1966 (15)	0.050 (6)*
H1B	0.3481 (15)	0.982 (2)	0.1566 (16)	0.064 (8)*
H6A	0.2244 (19)	0.107 (3)	0.139 (2)	0.081 (11)*
H6B	0.216 (2)	0.037 (3)	0.202 (2)	0.101 (11)*
H1A	0.5820 (18)	0.991 (3)	0.0909 (19)	0.084 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0391 (3)	0.0388 (3)	0.0625 (3)	0.0045 (2)	0.0193 (2)	−0.0015 (2)
S2	0.0593 (4)	0.1316 (7)	0.0589 (4)	0.0087 (4)	0.0176 (3)	0.0039 (4)
Cl1	0.0682 (4)	0.0399 (3)	0.0827 (4)	0.0033 (2)	0.0401 (3)	0.0043 (3)
O1	0.0450 (8)	0.0578 (10)	0.0997 (13)	0.0024 (8)	0.0397 (9)	0.0003 (9)
O2	0.0639 (10)	0.0454 (8)	0.0825 (11)	−0.0185 (7)	0.0355 (9)	−0.0010 (7)
O3	0.0550 (8)	0.0380 (7)	0.0798 (10)	−0.0010 (6)	0.0356 (8)	0.0015 (7)
O4	0.0398 (7)	0.0461 (8)	0.0767 (10)	0.0041 (6)	0.0225 (7)	−0.0011 (7)
O5	0.0624 (10)	0.0370 (8)	0.1272 (15)	−0.0113 (7)	0.0458 (10)	−0.0162 (9)
O6	0.0487 (10)	0.0547 (11)	0.136 (2)	0.0025 (9)	0.0409 (12)	0.0216 (12)
O7	0.1030 (16)	0.0985 (15)	0.1060 (16)	−0.0129 (12)	0.0583 (13)	−0.0253 (12)
N1	0.0355 (8)	0.0341 (8)	0.0575 (10)	0.0000 (7)	0.0164 (8)	−0.0003 (7)
N2	0.0369 (8)	0.0340 (8)	0.0471 (9)	−0.0005 (6)	0.0138 (7)	−0.0028 (7)
N3	0.0457 (9)	0.0379 (9)	0.0505 (10)	−0.0056 (8)	0.0223 (8)	−0.0078 (8)
N4	0.0310 (8)	0.0353 (8)	0.0376 (8)	−0.0010 (6)	0.0115 (7)	−0.0005 (6)
C1	0.0347 (10)	0.0510 (11)	0.0519 (12)	−0.0006 (9)	0.0161 (9)	0.0009 (9)
C2	0.0393 (11)	0.0554 (12)	0.0585 (13)	−0.0108 (9)	0.0216 (10)	0.0025 (10)
C3	0.0423 (10)	0.0441 (11)	0.0469 (11)	−0.0104 (9)	0.0136 (9)	0.0032 (9)
C4	0.0381 (10)	0.0417 (10)	0.0460 (11)	−0.0025 (8)	0.0124 (9)	0.0018 (8)
C5	0.0308 (9)	0.0412 (10)	0.0515 (11)	−0.0052 (8)	0.0137 (8)	0.0011 (8)
C6	0.0294 (9)	0.0412 (10)	0.0461 (10)	−0.0023 (8)	0.0106 (8)	0.0010 (8)
C7	0.0318 (9)	0.0421 (10)	0.0467 (11)	0.0004 (8)	0.0094 (8)	−0.0003 (8)
C8	0.0348 (9)	0.0344 (9)	0.0402 (10)	0.0024 (8)	0.0086 (8)	−0.0004 (8)
C9	0.0519 (12)	0.0317 (10)	0.0670 (14)	−0.0010 (9)	0.0231 (10)	−0.0025 (9)
C10	0.0424 (10)	0.0324 (9)	0.0476 (11)	−0.0023 (8)	0.0152 (9)	−0.0029 (8)
C11	0.0476 (11)	0.0366 (10)	0.0528 (12)	−0.0040 (9)	0.0196 (9)	−0.0068 (9)
C12	0.0401 (10)	0.0546 (12)	0.0435 (11)	−0.0049 (9)	0.0141 (9)	−0.0111 (9)
C13	0.0376 (10)	0.0365 (10)	0.0496 (11)	−0.0046 (8)	0.0160 (9)	−0.0068 (8)
C14	0.0340 (9)	0.0513 (12)	0.0484 (11)	0.0037 (8)	0.0182 (9)	−0.0021 (9)
C15	0.0374 (11)	0.0856 (17)	0.0615 (14)	0.0186 (11)	0.0112 (10)	−0.0040 (12)
C16	0.0601 (14)	0.0648 (14)	0.0591 (14)	0.0102 (11)	0.0243 (11)	−0.0146 (11)
C17	0.0418 (11)	0.0598 (13)	0.0418 (11)	0.0038 (10)	0.0059 (9)	0.0021 (9)
C18	0.0369 (11)	0.104 (2)	0.0640 (15)	0.0116 (13)	0.0050 (11)	0.0074 (14)
C19	0.0812 (18)	0.0825 (19)	0.0622 (15)	0.0096 (15)	0.0151 (14)	0.0290 (14)
C20	0.0854 (19)	0.0649 (16)	0.114 (2)	−0.0361 (15)	0.0526 (18)	−0.0080 (15)
C21	0.0552 (13)	0.0490 (12)	0.0750 (15)	−0.0040 (10)	0.0355 (12)	−0.0035 (11)
C22	0.127 (3)	0.222 (5)	0.151 (4)	0.017 (4)	0.087 (3)	0.079 (4)
C23	0.096 (2)	0.116 (3)	0.096 (2)	0.013 (2)	0.0277 (19)	−0.018 (2)

Geometric parameters (Å, º)

S1—C9	1.701 (2)	C9—H9A	0.9300
S1—C8	1.7298 (18)	C10—C11	1.481 (3)
S2—O7	1.477 (2)	C12—C13	1.509 (3)
S2—C23	1.757 (4)	C12—H12A	0.9700
S2—C22	1.771 (4)	C12—H12B	0.9700
O1—C1	1.356 (2)	C13—H13A	0.9700
O1—H1A	0.87 (3)	C13—H13B	0.9700
O2—C3	1.358 (2)	C14—C15	1.510 (3)
O2—C20	1.429 (3)	C14—C16	1.517 (3)
O3—C4	1.366 (2)	C14—H14A	0.9800
O3—C21	1.425 (2)	C15—H15A	0.9600
O4—C7	1.238 (2)	C15—H15B	0.9600
O5—C11	1.223 (2)	C15—H15C	0.9600
O6—H6A	0.78 (3)	C16—H16A	0.9600
O6—H6B	0.83 (4)	C16—H16B	0.9600
N1—C7	1.363 (2)	C16—H16C	0.9600
N1—C8	1.376 (2)	C17—C19	1.504 (3)
N1—H1B	0.81 (2)	C17—C18	1.518 (3)
N2—C8	1.300 (2)	C17—H17A	0.9800
N2—C10	1.381 (2)	C18—H18A	0.9600
N3—C11	1.338 (3)	C18—H18B	0.9600
N3—C12	1.449 (2)	C18—H18C	0.9600
N3—H3A	0.82 (2)	C19—H19A	0.9600
N4—C13	1.509 (2)	C19—H19B	0.9600
N4—C17	1.525 (2)	C19—H19C	0.9600
N4—C14	1.530 (2)	C20—H20A	0.9600
N4—H4A	0.88 (2)	C20—H20B	0.9600
C1—C2	1.390 (3)	C20—H20C	0.9600
C1—C6	1.393 (3)	C21—H21A	0.9600
C2—C3	1.371 (3)	C21—H21B	0.9600
C2—H2A	0.9300	C21—H21C	0.9600
C3—C4	1.403 (3)	C22—H22A	0.9600
C4—C5	1.367 (3)	C22—H22B	0.9600
C5—C6	1.409 (3)	C22—H22C	0.9600
C5—H5A	0.9300	C23—H23A	0.9600
C6—C7	1.461 (3)	C23—H23B	0.9600
C9—C10	1.347 (3)	C23—H23C	0.9600
C9—S1—C8	88.42 (9)	C12—C13—H13B	108.9
O7—S2—C23	107.00 (15)	N4—C13—H13B	108.9
O7—S2—C22	107.1 (2)	H13A—C13—H13B	107.7
C23—S2—C22	97.1 (2)	C15—C14—C16	110.55 (18)
C1—O1—H1A	105.1 (19)	C15—C14—N4	110.53 (15)
C3—O2—C20	117.53 (19)	C16—C14—N4	109.99 (16)
C4—O3—C21	116.69 (15)	C15—C14—H14A	108.6
H6A—O6—H6B	109 (3)	C16—C14—H14A	108.6
C7—N1—C8	123.94 (17)	N4—C14—H14A	108.6
C7—N1—H1B	123.2 (18)	C14—C15—H15A	109.5
C8—N1—H1B	112.7 (18)	C14—C15—H15B	109.5
C8—N2—C10	109.42 (15)	H15A—C15—H15B	109.5
C11—N3—C12	122.11 (18)	C14—C15—H15C	109.5
C11—N3—H3A	121.8 (16)	H15A—C15—H15C	109.5
C12—N3—H3A	116.0 (16)	H15B—C15—H15C	109.5
C13—N4—C17	112.32 (15)	C14—C16—H16A	109.5
C13—N4—C14	112.29 (14)	C14—C16—H16B	109.5
C17—N4—C14	112.71 (14)	H16A—C16—H16B	109.5
C13—N4—H4A	108.0 (13)	C14—C16—H16C	109.5
C17—N4—H4A	106.2 (13)	H16A—C16—H16C	109.5
C14—N4—H4A	104.7 (13)	H16B—C16—H16C	109.5
O1—C1—C2	117.02 (18)	C19—C17—C18	113.6 (2)
O1—C1—C6	122.65 (19)	C19—C17—N4	112.21 (18)
C2—C1—C6	120.33 (18)	C18—C17—N4	109.53 (16)
C3—C2—C1	120.90 (18)	C19—C17—H17A	107.0
C3—C2—H2A	119.5	C18—C17—H17A	107.0
C1—C2—H2A	119.5	N4—C17—H17A	107.0
O2—C3—C2	125.19 (18)	C17—C18—H18A	109.5
O2—C3—C4	115.16 (18)	C17—C18—H18B	109.5
C2—C3—C4	119.65 (18)	H18A—C18—H18B	109.5
O3—C4—C5	124.72 (17)	C17—C18—H18C	109.5
O3—C4—C3	115.78 (17)	H18A—C18—H18C	109.5
C5—C4—C3	119.50 (18)	H18B—C18—H18C	109.5
C4—C5—C6	121.69 (17)	C17—C19—H19A	109.5
C4—C5—H5A	119.2	C17—C19—H19B	109.5
C6—C5—H5A	119.2	H19A—C19—H19B	109.5
C1—C6—C5	117.90 (17)	C17—C19—H19C	109.5
C1—C6—C7	119.40 (17)	H19A—C19—H19C	109.5
C5—C6—C7	122.70 (16)	H19B—C19—H19C	109.5
O4—C7—N1	119.16 (17)	O2—C20—H20A	109.5
O4—C7—C6	122.19 (17)	O2—C20—H20B	109.5
N1—C7—C6	118.64 (16)	H20A—C20—H20B	109.5
N2—C8—N1	120.31 (16)	O2—C20—H20C	109.5
N2—C8—S1	115.61 (14)	H20A—C20—H20C	109.5
N1—C8—S1	124.08 (14)	H20B—C20—H20C	109.5
C10—C9—S1	111.08 (15)	O3—C21—H21A	109.5
C10—C9—H9A	124.5	O3—C21—H21B	109.5
S1—C9—H9A	124.5	H21A—C21—H21B	109.5
C9—C10—N2	115.45 (17)	O3—C21—H21C	109.5
C9—C10—C11	125.30 (17)	H21A—C21—H21C	109.5
N2—C10—C11	119.23 (16)	H21B—C21—H21C	109.5
O5—C11—N3	122.23 (19)	S2—C22—H22A	109.5
O5—C11—C10	122.07 (18)	S2—C22—H22B	109.5
N3—C11—C10	115.68 (17)	H22A—C22—H22B	109.5
N3—C12—C13	114.07 (17)	S2—C22—H22C	109.5
N3—C12—H12A	108.7	H22A—C22—H22C	109.5
C13—C12—H12A	108.7	H22B—C22—H22C	109.5
N3—C12—H12B	108.7	S2—C23—H23A	109.5
C13—C12—H12B	108.7	S2—C23—H23B	109.5
H12A—C12—H12B	107.6	H23A—C23—H23B	109.5
C12—C13—N4	113.55 (16)	S2—C23—H23C	109.5
C12—C13—H13A	108.9	H23A—C23—H23C	109.5
N4—C13—H13A	108.9	H23B—C23—H23C	109.5
O1—C1—C2—C3	−179.43 (19)	C7—N1—C8—N2	−177.74 (18)
C6—C1—C2—C3	0.8 (3)	C7—N1—C8—S1	1.8 (3)
C20—O2—C3—C2	−3.3 (3)	C9—S1—C8—N2	0.29 (16)
C20—O2—C3—C4	176.0 (2)	C9—S1—C8—N1	−179.22 (18)
C1—C2—C3—O2	−179.9 (2)	C8—S1—C9—C10	0.16 (17)
C1—C2—C3—C4	0.8 (3)	S1—C9—C10—N2	−0.6 (2)
C21—O3—C4—C5	15.7 (3)	S1—C9—C10—C11	177.64 (16)
C21—O3—C4—C3	−163.72 (18)	C8—N2—C10—C9	0.8 (2)
O2—C3—C4—O3	−1.6 (3)	C8—N2—C10—C11	−177.55 (17)
C2—C3—C4—O3	177.76 (18)	C12—N3—C11—O5	−0.8 (3)
O2—C3—C4—C5	178.91 (18)	C12—N3—C11—C10	177.43 (17)
C2—C3—C4—C5	−1.7 (3)	C9—C10—C11—O5	−1.5 (3)
O3—C4—C5—C6	−178.45 (18)	N2—C10—C11—O5	176.7 (2)
C3—C4—C5—C6	1.0 (3)	C9—C10—C11—N3	−179.7 (2)
O1—C1—C6—C5	178.72 (18)	N2—C10—C11—N3	−1.5 (3)
C2—C1—C6—C5	−1.6 (3)	C11—N3—C12—C13	84.2 (2)
O1—C1—C6—C7	−1.3 (3)	N3—C12—C13—N4	70.6 (2)
C2—C1—C6—C7	178.45 (19)	C17—N4—C13—C12	−130.48 (17)
C4—C5—C6—C1	0.7 (3)	C14—N4—C13—C12	101.25 (18)
C4—C5—C6—C7	−179.36 (18)	C13—N4—C14—C15	−53.8 (2)
C8—N1—C7—O4	0.0 (3)	C17—N4—C14—C15	178.13 (18)
C8—N1—C7—C6	179.58 (17)	C13—N4—C14—C16	−176.16 (17)
C1—C6—C7—O4	4.3 (3)	C17—N4—C14—C16	55.8 (2)
C5—C6—C7—O4	−175.72 (18)	C13—N4—C17—C19	−62.1 (2)
C1—C6—C7—N1	−175.27 (18)	C14—N4—C17—C19	65.9 (2)
C5—C6—C7—N1	4.7 (3)	C13—N4—C17—C18	65.1 (2)
C10—N2—C8—N1	178.90 (17)	C14—N4—C17—C18	−166.89 (19)
C10—N2—C8—S1	−0.6 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O6^i	0.81 (2)	2.06 (3)	2.857 (3)	172 (2)
N3—H3A···Cl1	0.82 (2)	2.55 (2)	3.2538 (18)	145 (2)
N4—H4A···Cl1	0.88 (2)	2.28 (2)	3.1530 (17)	173.9 (17)
O1—H1A···O4	0.87 (3)	1.77 (3)	2.564 (2)	151 (3)
O6—H6A···O7^ii	0.78 (3)	2.00 (3)	2.768 (3)	174 (3)
O6—H6B···Cl1^iii	0.83 (4)	2.33 (4)	3.156 (2)	172 (3)

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

(2AH-2DMSO-1EA)

Crystal data

2(C21H31N4O5S)·2(Cl)·C4H8O2·2(C2H6OS)·	Z = 2
Mr = 1218.37	F(000) = 1296
Triclinic, P1	Dx = 1.280 Mg m^−3
a = 11.5500 (13) Å	Mo Kα radiation, λ = 0.71073 Å
b = 15.6355 (16) Å	Cell parameters from 23497 reflections
c = 18.5836 (19) Å	θ = 3.1–33.2°
α = 93.782 (4)°	µ = 0.30 mm^−1
β = 99.353 (4)°	T = 301 K
γ = 105.965 (4)°	Prism, colorless
V = 3161.9 (6) Å^3	0.13 × 0.1 × 0.08 mm

Data collection

CCD diffractometer	14642 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.034
ωκ scans	θmax = 33.2°, θmin = 3.1°
Absorption correction: multi-scan Higashi, T. (1995)	h = −17→17
Tmin = 0.965, Tmax = 0.976	k = −24→19
70899 measured reflections	l = −28→28
23497 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.088	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.240	w = 1/[σ^2(Fo^2) + (0.0746P)^2 + 4.1354P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.001
23497 reflections	Δρmax = 0.81 e Å^−3
745 parameters	Δρmin = −0.69 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1A	0.68251 (7)	0.50925 (4)	0.23638 (3)	0.04457 (16)
S1B	0.44268 (8)	0.59758 (5)	0.40922 (4)	0.0529 (2)
S2A	0.98557 (8)	0.87297 (6)	0.31972 (4)	0.0590 (2)
S2B	0.66409 (11)	0.99029 (8)	0.48030 (6)	0.0668 (4)	0.879 (3)
S2B1	0.7231 (8)	1.0455 (5)	0.5060 (4)	0.060 (3)	0.121 (3)
C22B	0.6758 (6)	1.1055 (4)	0.4756 (3)	0.1049 (17)
H22A	0.6763	1.1185	0.4258	0.157*
H22B	0.6071	1.1187	0.4917	0.157*
H22C	0.7504	1.1416	0.5066	0.157*
C23B	0.8136 (4)	0.9950 (3)	0.4678 (2)	0.0805 (12)
H23A	0.8201	1.0030	0.4177	0.121*
H23B	0.8716	1.0443	0.4997	0.121*
H23C	0.8306	0.9401	0.4792	0.121*
O6B	0.6642 (3)	0.97774 (18)	0.55997 (14)	0.0804 (8)
Cl1A	0.78174 (7)	0.08579 (4)	0.28763 (4)	0.05029 (17)
Cl1B	0.13808 (6)	0.98122 (5)	0.13491 (4)	0.04849 (16)
N1A	0.82126 (19)	0.65732 (13)	0.18580 (9)	0.0346 (4)
N1B	0.5680 (2)	0.74748 (14)	0.35507 (10)	0.0396 (5)
N2A	0.8242 (2)	0.65558 (14)	0.31221 (10)	0.0391 (4)
N2B	0.5638 (2)	0.75168 (14)	0.48065 (10)	0.0378 (4)
N3B	0.6009 (2)	0.81779 (16)	0.62641 (11)	0.0454 (5)
N3A	0.8591 (2)	0.71744 (16)	0.45847 (12)	0.0477 (6)
N4B	0.57661 (19)	0.91676 (15)	0.81318 (10)	0.0377 (4)
N4A	0.9749 (2)	0.65790 (16)	0.60351 (13)	0.0482 (5)
O1B	0.69844 (19)	0.88905 (12)	0.30181 (8)	0.0444 (4)
O1A	0.96102 (19)	0.79521 (13)	0.13106 (9)	0.0458 (5)
O2B	0.69878 (18)	0.86265 (12)	0.04279 (8)	0.0435 (4)
O2A	0.9448 (2)	0.76501 (13)	−0.13086 (10)	0.0518 (5)
O3B	0.54582 (18)	0.70487 (12)	0.02337 (8)	0.0442 (4)
O3A	0.7741 (2)	0.61644 (14)	−0.14778 (9)	0.0560 (6)
O4A	0.70498 (19)	0.54297 (12)	0.10263 (9)	0.0483 (5)
O4B	0.4657 (2)	0.62808 (13)	0.27307 (10)	0.0578 (6)
O5A	0.7758 (2)	0.57808 (14)	0.48642 (10)	0.0553 (5)
O5B	0.5134 (2)	0.67962 (14)	0.65616 (10)	0.0541 (5)
O6A	0.9752 (3)	0.86433 (17)	0.39862 (12)	0.0686 (7)
O7	1.2280 (7)	0.7366 (7)	−0.0110 (5)	0.225 (4)
O8	1.1502 (4)	0.6321 (3)	0.0567 (4)	0.1432 (19)
C1B	0.6630 (2)	0.84014 (14)	0.23423 (10)	0.0310 (4)
C1A	0.9151 (2)	0.74884 (15)	0.06251 (11)	0.0320 (4)
C2B	0.7046 (2)	0.87798 (14)	0.17371 (11)	0.0332 (4)
H2BB	0.7594	0.9352	0.1802	0.040*
C2A	0.9566 (2)	0.78449 (15)	0.00144 (12)	0.0357 (5)
H2AB	1.0159	0.8397	0.0073	0.043*
C3B	0.6649 (2)	0.83098 (14)	0.10428 (11)	0.0309 (4)
C3A	0.9097 (2)	0.73794 (16)	−0.06792 (12)	0.0353 (5)
C4B	0.5817 (2)	0.74401 (14)	0.09436 (10)	0.0306 (4)
C4A	0.8174 (2)	0.65534 (15)	−0.07686 (11)	0.0359 (5)
C4	1.1544 (13)	0.6474 (13)	−0.0193 (14)	0.266 (11)
C5A	0.7793 (2)	0.62034 (15)	−0.01620 (11)	0.0345 (5)
H5AA	0.7201	0.5650	−0.0223	0.041*
C5B	0.5449 (2)	0.70634 (14)	0.15459 (11)	0.0311 (4)
H5BA	0.4929	0.6481	0.1482	0.037*
C6B	0.5835 (2)	0.75324 (14)	0.22579 (10)	0.0296 (4)
C6A	0.8269 (2)	0.66535 (14)	0.05512 (11)	0.0301 (4)
C7A	0.7798 (2)	0.61764 (15)	0.11470 (11)	0.0320 (4)
C7B	0.5347 (2)	0.70462 (15)	0.28468 (11)	0.0349 (5)
C8A	0.7838 (2)	0.61576 (15)	0.24494 (11)	0.0329 (4)
C8B	0.5311 (2)	0.70772 (15)	0.41493 (11)	0.0357 (5)
C9A	0.6966 (3)	0.51817 (18)	0.32980 (13)	0.0444 (6)
H9AA	0.6568	0.4738	0.3558	0.053*
C9B	0.4521 (3)	0.61156 (19)	0.50242 (14)	0.0495 (7)
H9BA	0.4168	0.5672	0.5298	0.059*
C10B	0.5181 (2)	0.69619 (17)	0.53057 (12)	0.0378 (5)
C10A	0.7738 (2)	0.59896 (17)	0.36073 (12)	0.0397 (5)
C11B	0.5439 (2)	0.73029 (18)	0.61050 (12)	0.0393 (5)
C11A	0.8029 (3)	0.63116 (19)	0.44060 (12)	0.0429 (6)
C12B	0.6404 (3)	0.8606 (2)	0.70175 (13)	0.0452 (6)
H12A	0.6965	0.9197	0.7025	0.054*
H12B	0.6841	0.8257	0.7306	0.054*
C12A	0.8800 (3)	0.7616 (2)	0.53285 (14)	0.0486 (6)
H12C	0.8079	0.7375	0.5539	0.058*
H12D	0.8896	0.8249	0.5304	0.058*
C13B	0.5337 (2)	0.86911 (18)	0.73632 (12)	0.0398 (5)
H13A	0.4880	0.9020	0.7066	0.048*
H13B	0.4792	0.8099	0.7375	0.048*
C13A	0.9907 (3)	0.75167 (18)	0.58354 (16)	0.0489 (6)
H13C	1.0614	0.7689	0.5600	0.059*
H13D	1.0070	0.7924	0.6281	0.059*
C14B	0.5305 (3)	0.9990 (2)	0.82208 (18)	0.0567 (8)
H14A	0.4410	0.9802	0.8069	0.068*
C14A	0.9389 (4)	0.6479 (3)	0.67923 (18)	0.0756 (11)
H14B	1.0070	0.6861	0.7162	0.091*
C15B	0.5851 (4)	1.0655 (3)	0.7717 (3)	0.0775 (11)
H15A	0.5635	1.0371	0.7220	0.116*
H15B	0.5535	1.1160	0.7749	0.116*
H15C	0.6727	1.0852	0.7864	0.116*
C15A	0.8267 (5)	0.6777 (5)	0.6840 (2)	0.110 (2)
H15D	0.8414	0.7386	0.6733	0.165*
H15E	0.7582	0.6400	0.6491	0.165*
H15F	0.8092	0.6737	0.7326	0.165*
C16B	0.5630 (4)	1.0420 (3)	0.9015 (2)	0.0811 (13)
H16A	0.5278	0.9990	0.9323	0.122*
H16B	0.6506	1.0616	0.9169	0.122*
H16C	0.5313	1.0925	0.9054	0.122*
C16A	0.9191 (7)	0.5513 (5)	0.6960 (4)	0.132 (2)
H16D	0.9917	0.5338	0.6926	0.198*
H16E	0.9021	0.5465	0.7446	0.198*
H16F	0.8511	0.5127	0.6611	0.198*
C17B	0.5508 (3)	0.8527 (2)	0.87079 (14)	0.0515 (7)
H17A	0.5862	0.8879	0.9188	0.062*
C17A	1.0861 (3)	0.6253 (2)	0.5953 (2)	0.0702 (10)
H17B	1.0683	0.5639	0.6083	0.084*
C18A	1.2010 (4)	0.6812 (3)	0.6487 (3)	0.1051 (19)
H18A	1.1851	0.6813	0.6978	0.158*
H18B	1.2671	0.6559	0.6454	0.158*
H18C	1.2229	0.7415	0.6364	0.158*
C18B	0.4150 (4)	0.8143 (4)	0.8690 (2)	0.0887 (14)
H18D	0.3787	0.8623	0.8736	0.133*
H18E	0.3773	0.7773	0.8233	0.133*
H18F	0.4028	0.7789	0.9089	0.133*
C19B	0.6172 (4)	0.7829 (2)	0.86393 (18)	0.0631 (9)
H19A	0.7026	0.8119	0.8655	0.095*
H19B	0.6084	0.7470	0.9038	0.095*
H19C	0.5829	0.7454	0.8181	0.095*
C19A	1.1030 (5)	0.6215 (3)	0.5163 (3)	0.0989 (16)
H19D	1.0283	0.5857	0.4853	0.148*
H19E	1.1237	0.6811	0.5023	0.148*
H19F	1.1678	0.5955	0.5113	0.148*
C20B	0.7879 (3)	0.94834 (19)	0.05079 (15)	0.0502 (7)
H20A	0.8041	0.9632	0.0034	0.075*
H20B	0.7572	0.9928	0.0728	0.075*
H20C	0.8624	0.9466	0.0815	0.075*
C20A	1.0405 (3)	0.8469 (2)	−0.12519 (18)	0.0625 (9)
H20D	1.0567	0.8586	−0.1732	0.094*
H20E	1.0157	0.8951	−0.1039	0.094*
H20F	1.1134	0.8422	−0.0946	0.094*
C21B	0.4638 (3)	0.61749 (18)	0.01029 (14)	0.0497 (7)
H21A	0.4457	0.5975	−0.0413	0.075*
H21B	0.5005	0.5777	0.0365	0.075*
H21C	0.3894	0.6179	0.0268	0.075*
C21A	0.6672 (4)	0.5437 (2)	−0.16111 (17)	0.0735 (12)
H21D	0.6461	0.5223	−0.2125	0.110*
H21E	0.6811	0.4965	−0.1335	0.110*
H21F	0.6013	0.5625	−0.1464	0.110*
C22A	1.0421 (4)	0.9890 (3)	0.3148 (2)	0.0690 (9)
H22D	1.0508	0.9989	0.2652	0.104*
H22E	0.9858	1.0187	0.3296	0.104*
H22F	1.1204	1.0124	0.3468	0.104*
C23A	1.1194 (4)	0.8443 (3)	0.3090 (2)	0.0823 (12)
H23D	1.1312	0.8485	0.2592	0.123*
H23E	1.1887	0.8846	0.3417	0.123*
H23F	1.1113	0.7841	0.3201	0.123*
C24	1.0980 (14)	0.5877 (11)	−0.0838 (7)	0.280 (12)
H24A	1.0535	0.5312	−0.0709	0.420*
H24B	1.0425	0.6122	−0.1142	0.420*
H24C	1.1597	0.5793	−0.1101	0.420*
C25	1.2036 (7)	0.6935 (6)	0.1294 (7)	0.190 (5)
H25A	1.2924	0.7093	0.1409	0.228*
H25B	1.1775	0.7474	0.1299	0.228*
C26	1.1457 (16)	0.6312 (13)	0.1784 (8)	0.349 (14)
H26A	1.1697	0.6596	0.2281	0.523*
H26B	1.0581	0.6157	0.1640	0.523*
H26C	1.1715	0.5780	0.1749	0.523*
H1AB	0.875 (3)	0.719 (2)	0.1951 (17)	0.044 (8)*
H4BA	0.658 (3)	0.939 (2)	0.8211 (17)	0.042 (8)*
H3BA	0.620 (3)	0.854 (2)	0.5943 (19)	0.052 (9)*
H3AA	0.882 (3)	0.750 (2)	0.429 (2)	0.055 (10)*
H4AA	0.907 (3)	0.624 (2)	0.5715 (19)	0.052 (9)*
H1BB	0.724 (4)	0.948 (3)	0.297 (2)	0.072 (12)*
H1BA	0.605 (3)	0.801 (3)	0.361 (2)	0.063 (11)*
H1AA	1.012 (3)	0.845 (2)	0.1261 (19)	0.055 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1A	0.0548 (4)	0.0382 (3)	0.0290 (3)	−0.0039 (3)	0.0066 (2)	0.0002 (2)
S1B	0.0748 (5)	0.0375 (3)	0.0325 (3)	−0.0083 (3)	0.0162 (3)	−0.0031 (2)
S2A	0.0634 (5)	0.0708 (5)	0.0343 (3)	0.0045 (4)	0.0120 (3)	0.0028 (3)
S2B	0.0787 (7)	0.0577 (6)	0.0475 (5)	−0.0032 (5)	0.0019 (4)	0.0137 (4)
S2B1	0.084 (6)	0.053 (4)	0.043 (3)	0.020 (4)	0.013 (3)	0.005 (3)
C22B	0.120 (4)	0.093 (3)	0.121 (4)	0.040 (3)	0.042 (3)	0.059 (3)
C23B	0.104 (3)	0.101 (3)	0.0427 (17)	0.049 (3)	0.0025 (18)	−0.0020 (18)
O6B	0.115 (2)	0.0657 (15)	0.0532 (13)	0.0067 (15)	0.0243 (14)	0.0227 (12)
Cl1A	0.0571 (4)	0.0381 (3)	0.0439 (3)	0.0027 (3)	−0.0017 (3)	−0.0028 (2)
Cl1B	0.0427 (3)	0.0486 (3)	0.0436 (3)	−0.0010 (3)	0.0035 (2)	0.0034 (3)
N1A	0.0391 (10)	0.0369 (9)	0.0206 (7)	0.0009 (8)	0.0041 (7)	−0.0001 (6)
N1B	0.0553 (12)	0.0341 (9)	0.0192 (7)	−0.0027 (9)	0.0081 (8)	−0.0030 (7)
N2A	0.0464 (11)	0.0409 (10)	0.0222 (8)	0.0014 (8)	0.0044 (7)	0.0017 (7)
N2B	0.0489 (11)	0.0376 (10)	0.0220 (8)	0.0033 (8)	0.0102 (7)	0.0000 (7)
N3B	0.0602 (14)	0.0457 (11)	0.0220 (8)	−0.0004 (10)	0.0122 (8)	0.0015 (8)
N3A	0.0660 (15)	0.0447 (12)	0.0256 (9)	0.0042 (11)	0.0102 (9)	0.0039 (8)
N4B	0.0326 (9)	0.0516 (12)	0.0247 (8)	0.0094 (8)	0.0018 (7)	−0.0030 (7)
N4A	0.0508 (13)	0.0439 (12)	0.0398 (11)	0.0054 (10)	−0.0033 (10)	−0.0005 (9)
O1B	0.0646 (12)	0.0341 (8)	0.0196 (7)	−0.0063 (8)	0.0048 (7)	−0.0075 (6)
O1A	0.0558 (11)	0.0387 (9)	0.0263 (7)	−0.0098 (8)	0.0051 (7)	−0.0053 (6)
O2B	0.0548 (10)	0.0403 (9)	0.0222 (7)	−0.0065 (8)	0.0053 (7)	0.0033 (6)
O2A	0.0648 (12)	0.0466 (10)	0.0317 (8)	−0.0082 (9)	0.0175 (8)	0.0030 (7)
O3B	0.0598 (11)	0.0375 (8)	0.0203 (7)	−0.0067 (8)	0.0047 (7)	−0.0050 (6)
O3A	0.0665 (13)	0.0547 (11)	0.0238 (8)	−0.0183 (9)	0.0107 (8)	−0.0080 (7)
O4A	0.0615 (12)	0.0392 (9)	0.0286 (8)	−0.0086 (8)	0.0065 (8)	−0.0012 (7)
O4B	0.0879 (16)	0.0372 (9)	0.0281 (8)	−0.0138 (9)	0.0120 (9)	−0.0038 (7)
O5A	0.0681 (13)	0.0552 (11)	0.0267 (8)	−0.0068 (10)	0.0045 (8)	0.0089 (8)
O5B	0.0771 (14)	0.0512 (11)	0.0306 (8)	0.0066 (10)	0.0184 (9)	0.0113 (8)
O6A	0.0921 (18)	0.0638 (14)	0.0377 (10)	−0.0035 (13)	0.0235 (11)	0.0035 (9)
O7	0.164 (6)	0.284 (10)	0.298 (10)	0.118 (7)	0.120 (6)	0.116 (8)
O8	0.099 (3)	0.118 (4)	0.218 (6)	0.046 (3)	0.031 (4)	−0.002 (4)
C1B	0.0377 (10)	0.0312 (9)	0.0182 (8)	0.0048 (8)	0.0005 (7)	−0.0048 (7)
C1A	0.0335 (10)	0.0321 (10)	0.0244 (9)	0.0026 (8)	0.0032 (7)	−0.0030 (7)
C2B	0.0387 (11)	0.0290 (9)	0.0225 (8)	−0.0015 (8)	0.0008 (8)	−0.0024 (7)
C2A	0.0370 (11)	0.0313 (10)	0.0313 (10)	−0.0024 (8)	0.0085 (8)	−0.0009 (8)
C3B	0.0347 (10)	0.0324 (9)	0.0207 (8)	0.0039 (8)	0.0026 (7)	0.0013 (7)
C3A	0.0379 (11)	0.0370 (11)	0.0273 (9)	0.0025 (9)	0.0110 (8)	0.0023 (8)
C4B	0.0376 (10)	0.0291 (9)	0.0188 (8)	0.0033 (8)	0.0014 (7)	−0.0044 (6)
C4A	0.0426 (12)	0.0352 (10)	0.0226 (9)	0.0004 (9)	0.0066 (8)	−0.0030 (7)
C4	0.150 (9)	0.316 (19)	0.48 (3)	0.173 (12)	0.198 (15)	0.27 (2)
C5A	0.0378 (11)	0.0329 (10)	0.0241 (9)	−0.0025 (8)	0.0054 (8)	−0.0030 (7)
C5B	0.0377 (10)	0.0269 (9)	0.0225 (8)	0.0030 (8)	0.0014 (7)	−0.0036 (7)
C6B	0.0386 (10)	0.0275 (9)	0.0178 (7)	0.0048 (8)	0.0014 (7)	−0.0014 (6)
C6A	0.0315 (10)	0.0325 (9)	0.0218 (8)	0.0037 (8)	0.0036 (7)	−0.0011 (7)
C7A	0.0358 (10)	0.0350 (10)	0.0221 (8)	0.0055 (8)	0.0054 (7)	0.0008 (7)
C7B	0.0470 (12)	0.0319 (10)	0.0208 (8)	0.0048 (9)	0.0055 (8)	−0.0010 (7)
C8A	0.0376 (11)	0.0350 (10)	0.0232 (8)	0.0054 (8)	0.0060 (8)	0.0040 (7)
C8B	0.0456 (12)	0.0342 (10)	0.0226 (9)	0.0019 (9)	0.0106 (8)	0.0013 (7)
C9A	0.0547 (15)	0.0419 (12)	0.0301 (10)	0.0018 (11)	0.0094 (10)	0.0074 (9)
C9B	0.0666 (18)	0.0430 (13)	0.0323 (11)	−0.0006 (12)	0.0185 (11)	0.0047 (10)
C10B	0.0443 (12)	0.0410 (12)	0.0260 (9)	0.0071 (10)	0.0102 (9)	0.0021 (8)
C10A	0.0481 (13)	0.0416 (12)	0.0257 (9)	0.0070 (10)	0.0067 (9)	0.0043 (8)
C11B	0.0471 (13)	0.0457 (12)	0.0244 (9)	0.0089 (10)	0.0122 (9)	0.0048 (8)
C11A	0.0499 (14)	0.0500 (14)	0.0224 (9)	0.0046 (11)	0.0047 (9)	0.0069 (9)
C12B	0.0461 (13)	0.0573 (15)	0.0242 (10)	0.0022 (11)	0.0095 (9)	−0.0030 (9)
C12A	0.0641 (17)	0.0502 (14)	0.0297 (11)	0.0163 (13)	0.0070 (11)	−0.0020 (10)
C13B	0.0399 (12)	0.0506 (13)	0.0218 (9)	0.0067 (10)	−0.0009 (8)	−0.0012 (8)
C13A	0.0532 (15)	0.0408 (13)	0.0443 (14)	0.0075 (11)	−0.0001 (11)	−0.0045 (10)
C14B	0.0467 (15)	0.0660 (19)	0.0595 (18)	0.0278 (14)	0.0029 (13)	−0.0100 (14)
C14A	0.093 (3)	0.088 (3)	0.0366 (15)	0.018 (2)	−0.0017 (16)	0.0139 (16)
C15B	0.077 (3)	0.0546 (19)	0.105 (3)	0.0317 (19)	0.008 (2)	0.012 (2)
C15A	0.123 (4)	0.190 (6)	0.051 (2)	0.078 (4)	0.045 (3)	0.041 (3)
C16B	0.073 (2)	0.099 (3)	0.072 (2)	0.044 (2)	0.0012 (19)	−0.033 (2)
C16A	0.173 (6)	0.127 (5)	0.105 (4)	0.040 (5)	0.039 (4)	0.068 (4)
C17B	0.0504 (15)	0.076 (2)	0.0265 (11)	0.0119 (14)	0.0109 (10)	0.0104 (11)
C17A	0.061 (2)	0.0436 (16)	0.096 (3)	0.0132 (14)	−0.0017 (19)	−0.0117 (17)
C18A	0.062 (2)	0.067 (2)	0.165 (5)	0.025 (2)	−0.033 (3)	−0.022 (3)
C18B	0.062 (2)	0.133 (4)	0.066 (2)	0.006 (2)	0.0275 (19)	0.033 (2)
C19B	0.080 (2)	0.068 (2)	0.0438 (15)	0.0209 (18)	0.0126 (15)	0.0246 (14)
C19A	0.088 (3)	0.082 (3)	0.129 (4)	0.019 (2)	0.048 (3)	−0.017 (3)
C20B	0.0546 (16)	0.0463 (14)	0.0362 (12)	−0.0064 (12)	0.0050 (11)	0.0089 (10)
C20A	0.074 (2)	0.0490 (16)	0.0521 (16)	−0.0100 (15)	0.0244 (15)	0.0111 (13)
C21B	0.0624 (17)	0.0382 (12)	0.0322 (11)	−0.0049 (11)	0.0022 (11)	−0.0098 (9)
C21A	0.079 (2)	0.066 (2)	0.0411 (15)	−0.0279 (17)	0.0082 (15)	−0.0193 (14)
C22A	0.074 (2)	0.076 (2)	0.063 (2)	0.0183 (19)	0.0280 (18)	0.0231 (18)
C23A	0.093 (3)	0.104 (3)	0.055 (2)	0.041 (3)	0.012 (2)	−0.001 (2)
C24	0.278 (17)	0.37 (2)	0.224 (14)	0.243 (17)	−0.054 (12)	−0.111 (14)
C25	0.096 (5)	0.162 (7)	0.296 (13)	0.079 (5)	−0.037 (6)	−0.086 (9)
C26	0.41 (2)	0.56 (3)	0.360 (19)	0.42 (2)	0.280 (18)	0.34 (2)

Geometric parameters (Å, º)

S1A—C9A	1.710 (2)	C6A—C7A	1.470 (3)
S1A—C8A	1.732 (2)	C9A—C10A	1.356 (4)
S1B—C9B	1.713 (3)	C9A—H9AA	0.9300
S1B—C8B	1.730 (2)	C9B—C10B	1.353 (4)
S2A—O6A	1.502 (2)	C9B—H9BA	0.9300
S2A—C23A	1.761 (5)	C10B—C11B	1.498 (3)
S2A—C22A	1.765 (4)	C10A—C11A	1.489 (3)
S2B—O6B	1.506 (3)	C12B—C13B	1.511 (4)
S2B—C23B	1.762 (5)	C12B—H12A	0.9700
S2B—C22B	1.779 (5)	C12B—H12B	0.9700
S2B1—C22B	1.322 (9)	C12A—C13A	1.511 (4)
S2B1—O6B	1.600 (8)	C12A—H12C	0.9700
S2B1—C23B	1.687 (9)	C12A—H12D	0.9700
C22B—H22A	0.9600	C13B—H13A	0.9700
C22B—H22B	0.9600	C13B—H13B	0.9700
C22B—H22C	0.9600	C13A—H13C	0.9700
C23B—H23A	0.9600	C13A—H13D	0.9700
C23B—H23B	0.9600	C14B—C15B	1.521 (6)
C23B—H23C	0.9600	C14B—C16B	1.524 (5)
N1A—C7A	1.372 (3)	C14B—H14A	0.9800
N1A—C8A	1.382 (3)	C14A—C15A	1.506 (7)
N1A—H1AB	0.98 (3)	C14A—C16A	1.525 (7)
N1B—C7B	1.374 (3)	C14A—H14B	0.9800
N1B—C8B	1.380 (3)	C15B—H15A	0.9600
N1B—H1BA	0.82 (4)	C15B—H15B	0.9600
N2A—C8A	1.310 (3)	C15B—H15C	0.9600
N2A—C10A	1.388 (3)	C15A—H15D	0.9600
N2B—C8B	1.305 (3)	C15A—H15E	0.9600
N2B—C10B	1.381 (3)	C15A—H15F	0.9600
N3B—C11B	1.334 (3)	C16B—H16A	0.9600
N3B—C12B	1.455 (3)	C16B—H16B	0.9600
N3B—H3BA	0.86 (4)	C16B—H16C	0.9600
N3A—C11A	1.319 (4)	C16A—H16D	0.9600
N3A—C12A	1.456 (3)	C16A—H16E	0.9600
N3A—H3AA	0.81 (4)	C16A—H16F	0.9600
N4B—C13B	1.506 (3)	C17B—C19B	1.506 (5)
N4B—C17B	1.523 (3)	C17B—C18B	1.511 (5)
N4B—C14B	1.531 (4)	C17B—H17A	0.9800
N4B—H4BA	0.90 (3)	C17A—C19A	1.511 (7)
N4A—C13A	1.506 (4)	C17A—C18A	1.526 (5)
N4A—C17A	1.531 (5)	C17A—H17B	0.9800
N4A—C14A	1.537 (4)	C18A—H18A	0.9600
N4A—H4AA	0.91 (4)	C18A—H18B	0.9600
O1B—C1B	1.365 (2)	C18A—H18C	0.9600
O1B—H1BB	0.90 (4)	C18B—H18D	0.9600
O1A—C1A	1.370 (2)	C18B—H18E	0.9600
O1A—H1AA	0.86 (4)	C18B—H18F	0.9600
O2B—C3B	1.348 (3)	C19B—H19A	0.9600
O2B—C20B	1.429 (3)	C19B—H19B	0.9600
O2A—C3A	1.355 (3)	C19B—H19C	0.9600
O2A—C20A	1.428 (3)	C19A—H19D	0.9600
O3B—C4B	1.365 (2)	C19A—H19E	0.9600
O3B—C21B	1.412 (3)	C19A—H19F	0.9600
O3A—C4A	1.367 (3)	C20B—H20A	0.9600
O3A—C21A	1.404 (3)	C20B—H20B	0.9600
O4A—C7A	1.228 (3)	C20B—H20C	0.9600
O4B—C7B	1.224 (3)	C20A—H20D	0.9600
O5A—C11A	1.244 (3)	C20A—H20E	0.9600
O5B—C11B	1.227 (3)	C20A—H20F	0.9600
O7—C4	1.403 (19)	C21B—H21A	0.9600
O8—C4	1.454 (19)	C21B—H21B	0.9600
O8—C25	1.537 (10)	C21B—H21C	0.9600
C1B—C6B	1.397 (3)	C21A—H21D	0.9600
C1B—C2B	1.397 (3)	C21A—H21E	0.9600
C1A—C2A	1.394 (3)	C21A—H21F	0.9600
C1A—C6A	1.400 (3)	C22A—H22D	0.9600
C2B—C3B	1.383 (3)	C22A—H22E	0.9600
C2B—H2BB	0.9300	C22A—H22F	0.9600
C2A—C3A	1.384 (3)	C23A—H23D	0.9600
C2A—H2AB	0.9300	C23A—H23E	0.9600
C3B—C4B	1.413 (3)	C23A—H23F	0.9600
C3A—C4A	1.410 (3)	C24—H24A	0.9600
C4B—C5B	1.373 (3)	C24—H24B	0.9600
C4A—C5A	1.369 (3)	C24—H24C	0.9600
C4—C24	1.41 (3)	C25—C26	1.477 (14)
C5A—C6A	1.408 (3)	C25—H25A	0.9700
C5A—H5AA	0.9300	C25—H25B	0.9700
C5B—C6B	1.410 (3)	C26—H26A	0.9600
C5B—H5BA	0.9300	C26—H26B	0.9600
C6B—C7B	1.472 (3)	C26—H26C	0.9600
C9A—S1A—C8A	88.98 (11)	N4B—C13B—H13A	109.3
C9B—S1B—C8B	88.63 (12)	C12B—C13B—H13A	109.3
O6A—S2A—C23A	105.46 (19)	N4B—C13B—H13B	109.3
O6A—S2A—C22A	105.49 (16)	C12B—C13B—H13B	109.3
C23A—S2A—C22A	97.6 (2)	H13A—C13B—H13B	108.0
O6B—S2B—C23B	105.05 (19)	N4A—C13A—C12A	113.3 (2)
O6B—S2B—C22B	104.9 (2)	N4A—C13A—H13C	108.9
C23B—S2B—C22B	97.6 (3)	C12A—C13A—H13C	108.9
C22B—S2B1—O6B	126.2 (7)	N4A—C13A—H13D	108.9
C22B—S2B1—C23B	124.2 (6)	C12A—C13A—H13D	108.9
O6B—S2B1—C23B	104.5 (5)	H13C—C13A—H13D	107.7
S2B—C22B—H22A	109.5	C15B—C14B—C16B	110.8 (3)
S2B—C22B—H22B	109.5	C15B—C14B—N4B	108.6 (3)
H22A—C22B—H22B	109.5	C16B—C14B—N4B	111.6 (3)
S2B—C22B—H22C	109.5	C15B—C14B—H14A	108.6
H22A—C22B—H22C	109.5	C16B—C14B—H14A	108.6
H22B—C22B—H22C	109.5	N4B—C14B—H14A	108.6
S2B—C23B—H23A	109.5	C15A—C14A—C16A	111.0 (5)
S2B—C23B—H23B	109.5	C15A—C14A—N4A	111.5 (3)
H23A—C23B—H23B	109.5	C16A—C14A—N4A	110.0 (4)
S2B—C23B—H23C	109.5	C15A—C14A—H14B	108.1
H23A—C23B—H23C	109.5	C16A—C14A—H14B	108.1
H23B—C23B—H23C	109.5	N4A—C14A—H14B	108.1
C7A—N1A—C8A	122.55 (19)	C14B—C15B—H15A	109.5
C7A—N1A—H1AB	119.1 (18)	C14B—C15B—H15B	109.5
C8A—N1A—H1AB	118.3 (18)	H15A—C15B—H15B	109.5
C7B—N1B—C8B	123.4 (2)	C14B—C15B—H15C	109.5
C7B—N1B—H1BA	118 (3)	H15A—C15B—H15C	109.5
C8B—N1B—H1BA	118 (3)	H15B—C15B—H15C	109.5
C8A—N2A—C10A	109.4 (2)	C14A—C15A—H15D	109.5
C8B—N2B—C10B	109.5 (2)	C14A—C15A—H15E	109.5
C11B—N3B—C12B	121.9 (2)	H15D—C15A—H15E	109.5
C11B—N3B—H3BA	124 (2)	C14A—C15A—H15F	109.5
C12B—N3B—H3BA	114 (2)	H15D—C15A—H15F	109.5
C11A—N3A—C12A	122.7 (2)	H15E—C15A—H15F	109.5
C11A—N3A—H3AA	122 (3)	C14B—C16B—H16A	109.5
C12A—N3A—H3AA	115 (3)	C14B—C16B—H16B	109.5
C13B—N4B—C17B	112.0 (2)	H16A—C16B—H16B	109.5
C13B—N4B—C14B	111.5 (2)	C14B—C16B—H16C	109.5
C17B—N4B—C14B	114.7 (2)	H16A—C16B—H16C	109.5
C13B—N4B—H4BA	108 (2)	H16B—C16B—H16C	109.5
C17B—N4B—H4BA	105 (2)	C14A—C16A—H16D	109.5
C14B—N4B—H4BA	104 (2)	C14A—C16A—H16E	109.5
C13A—N4A—C17A	112.0 (3)	H16D—C16A—H16E	109.5
C13A—N4A—C14A	111.8 (3)	C14A—C16A—H16F	109.5
C17A—N4A—C14A	113.3 (3)	H16D—C16A—H16F	109.5
C13A—N4A—H4AA	104 (2)	H16E—C16A—H16F	109.5
C17A—N4A—H4AA	111 (2)	C19B—C17B—C18B	113.9 (4)
C14A—N4A—H4AA	104 (2)	C19B—C17B—N4B	109.9 (2)
C1B—O1B—H1BB	109 (3)	C18B—C17B—N4B	112.0 (3)
C1A—O1A—H1AA	107 (2)	C19B—C17B—H17A	106.9
C3B—O2B—C20B	117.50 (18)	C18B—C17B—H17A	106.9
C3A—O2A—C20A	117.5 (2)	N4B—C17B—H17A	106.9
C4B—O3B—C21B	117.38 (18)	C19A—C17A—C18A	113.0 (4)
C4A—O3A—C21A	117.3 (2)	C19A—C17A—N4A	110.6 (3)
C4—O8—C25	132.3 (12)	C18A—C17A—N4A	111.4 (3)
O1B—C1B—C6B	119.78 (19)	C19A—C17A—H17B	107.2
O1B—C1B—C2B	119.75 (19)	C18A—C17A—H17B	107.2
C6B—C1B—C2B	120.46 (17)	N4A—C17A—H17B	107.2
O1A—C1A—C2A	120.12 (19)	C17A—C18A—H18A	109.5
O1A—C1A—C6A	118.99 (19)	C17A—C18A—H18B	109.5
C2A—C1A—C6A	120.88 (18)	H18A—C18A—H18B	109.5
C3B—C2B—C1B	120.50 (19)	C17A—C18A—H18C	109.5
C3B—C2B—H2BB	119.8	H18A—C18A—H18C	109.5
C1B—C2B—H2BB	119.8	H18B—C18A—H18C	109.5
C3A—C2A—C1A	120.20 (19)	C17B—C18B—H18D	109.5
C3A—C2A—H2AB	119.9	C17B—C18B—H18E	109.5
C1A—C2A—H2AB	119.9	H18D—C18B—H18E	109.5
O2B—C3B—C2B	124.52 (19)	C17B—C18B—H18F	109.5
O2B—C3B—C4B	115.65 (17)	H18D—C18B—H18F	109.5
C2B—C3B—C4B	119.82 (19)	H18E—C18B—H18F	109.5
O2A—C3A—C2A	125.4 (2)	C17B—C19B—H19A	109.5
O2A—C3A—C4A	114.84 (19)	C17B—C19B—H19B	109.5
C2A—C3A—C4A	119.77 (19)	H19A—C19B—H19B	109.5
O3B—C4B—C5B	125.97 (18)	C17B—C19B—H19C	109.5
O3B—C4B—C3B	114.91 (18)	H19A—C19B—H19C	109.5
C5B—C4B—C3B	119.11 (17)	H19B—C19B—H19C	109.5
O3A—C4A—C5A	125.5 (2)	C17A—C19A—H19D	109.5
O3A—C4A—C3A	115.20 (19)	C17A—C19A—H19E	109.5
C5A—C4A—C3A	119.32 (19)	H19D—C19A—H19E	109.5
O7—C4—C24	129.8 (16)	C17A—C19A—H19F	109.5
O7—C4—O8	101.4 (19)	H19D—C19A—H19F	109.5
C24—C4—O8	128.7 (15)	H19E—C19A—H19F	109.5
C4A—C5A—C6A	122.1 (2)	O2B—C20B—H20A	109.5
C4A—C5A—H5AA	118.9	O2B—C20B—H20B	109.5
C6A—C5A—H5AA	118.9	H20A—C20B—H20B	109.5
C4B—C5B—C6B	121.98 (19)	O2B—C20B—H20C	109.5
C4B—C5B—H5BA	119.0	H20A—C20B—H20C	109.5
C6B—C5B—H5BA	119.0	H20B—C20B—H20C	109.5
C1B—C6B—C5B	118.06 (18)	O2A—C20A—H20D	109.5
C1B—C6B—C7B	126.21 (17)	O2A—C20A—H20E	109.5
C5B—C6B—C7B	115.73 (18)	H20D—C20A—H20E	109.5
C1A—C6A—C5A	117.63 (19)	O2A—C20A—H20F	109.5
C1A—C6A—C7A	126.75 (18)	H20D—C20A—H20F	109.5
C5A—C6A—C7A	115.61 (18)	H20E—C20A—H20F	109.5
O4A—C7A—N1A	119.1 (2)	O3B—C21B—H21A	109.5
O4A—C7A—C6A	121.79 (19)	O3B—C21B—H21B	109.5
N1A—C7A—C6A	119.12 (19)	H21A—C21B—H21B	109.5
O4B—C7B—N1B	119.2 (2)	O3B—C21B—H21C	109.5
O4B—C7B—C6B	122.50 (19)	H21A—C21B—H21C	109.5
N1B—C7B—C6B	118.27 (19)	H21B—C21B—H21C	109.5
N2A—C8A—N1A	121.2 (2)	O3A—C21A—H21D	109.5
N2A—C8A—S1A	115.41 (16)	O3A—C21A—H21E	109.5
N1A—C8A—S1A	123.38 (16)	H21D—C21A—H21E	109.5
N2B—C8B—N1B	121.1 (2)	O3A—C21A—H21F	109.5
N2B—C8B—S1B	115.56 (16)	H21D—C21A—H21F	109.5
N1B—C8B—S1B	123.29 (16)	H21E—C21A—H21F	109.5
C10A—C9A—S1A	110.48 (18)	S2A—C22A—H22D	109.5
C10A—C9A—H9AA	124.8	S2A—C22A—H22E	109.5
S1A—C9A—H9AA	124.8	H22D—C22A—H22E	109.5
C10B—C9B—S1B	110.47 (19)	S2A—C22A—H22F	109.5
C10B—C9B—H9BA	124.8	H22D—C22A—H22F	109.5
S1B—C9B—H9BA	124.8	H22E—C22A—H22F	109.5
C9B—C10B—N2B	115.8 (2)	S2A—C23A—H23D	109.5
C9B—C10B—C11B	124.0 (2)	S2A—C23A—H23E	109.5
N2B—C10B—C11B	120.2 (2)	H23D—C23A—H23E	109.5
C9A—C10A—N2A	115.7 (2)	S2A—C23A—H23F	109.5
C9A—C10A—C11A	125.0 (2)	H23D—C23A—H23F	109.5
N2A—C10A—C11A	119.2 (2)	H23E—C23A—H23F	109.5
O5B—C11B—N3B	124.4 (2)	C4—C24—H24A	109.5
O5B—C11B—C10B	120.8 (2)	C4—C24—H24B	109.5
N3B—C11B—C10B	114.8 (2)	H24A—C24—H24B	109.5
O5A—C11A—N3A	123.5 (2)	C4—C24—H24C	109.5
O5A—C11A—C10A	120.6 (2)	H24A—C24—H24C	109.5
N3A—C11A—C10A	115.9 (2)	H24B—C24—H24C	109.5
N3B—C12B—C13B	112.1 (2)	C26—C25—O8	97.8 (10)
N3B—C12B—H12A	109.2	C26—C25—H25A	112.2
C13B—C12B—H12A	109.2	O8—C25—H25A	112.2
N3B—C12B—H12B	109.2	C26—C25—H25B	112.2
C13B—C12B—H12B	109.2	O8—C25—H25B	112.2
H12A—C12B—H12B	107.9	H25A—C25—H25B	109.8
N3A—C12A—C13A	114.7 (3)	C25—C26—H26A	109.5
N3A—C12A—H12C	108.6	C25—C26—H26B	109.5
C13A—C12A—H12C	108.6	H26A—C26—H26B	109.5
N3A—C12A—H12D	108.6	C25—C26—H26C	109.5
C13A—C12A—H12D	108.6	H26A—C26—H26C	109.5
H12C—C12A—H12D	107.6	H26B—C26—H26C	109.5
N4B—C13B—C12B	111.43 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1AB···O1A	0.98 (3)	1.93 (3)	2.683 (3)	131 (3)
N3B—H3BA···O6B	0.86 (4)	2.04 (3)	2.830 (3)	153 (3)
N3A—H3AA···O6A	0.81 (4)	1.98 (4)	2.727 (3)	154 (4)
N1B—H1BA···O1B	0.82 (4)	2.01 (4)	2.662 (3)	137 (3)
N4A—H4AA···O5A	0.91 (4)	1.94 (4)	2.832 (3)	164 (3)
N4B—H4BA···Cl1B^i	0.90 (3)	2.32 (3)	3.195 (2)	166 (3)
O1B—H1BB···Cl1A^ii	0.90 (4)	2.10 (4)	3.003 (2)	178 (4)
O1A—H1AA···Cl1B^iii	0.86 (4)	2.21 (4)	3.0495 (19)	169 (3)

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