2-(Acetyl­amino)-N-benz­yl-2-(ethyl­sulfin­yl)acetamide: structural basis for lack of anticonvulsant activity

In the crystal structure of the title compound, C₁₃H₁₈N₂O₃S, there are two independent mol­ecules in the asymmetric unit. Both mol­ecules have linearly extended conformations, with inter­planar angles between the two amide groups of 150.4 (3) and 148.8 (3)°. In addition to the standard N—H...O hydrogen bonds, which form infinite mol­ecular chains parallel to the a axis, a host of weak non-standard C—H...O bonds and van der Waals contacts contribute to the crystal packing. Although the mol­ecule contains stereochemical features consonant with anticonvulsant properties, steric inter­ference by the ethylsulfinyl group may prevent inter­actions with receptors.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.014 Å
• R factor = 0.077
• wR factor = 0.188
• Data-to-parameter ratio = 8.7

checkCIF/PLATON results

No syntax errors found



Alert level A
THETM01_ALERT_3_A  The value of sine(theta_max)/wavelength is less than 0.550
            Calculated sin(theta_max)/wavelength =    0.4968

Author Response: ...'see the _exptl_special_details item'

PLAT023_ALERT_3_A Resolution (too) Low [sin(th)/Lambda < 0.6].....      49.99 Deg.

Author Response: ...'see the _exptl_special_details item'

PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............      49.99 Deg.

Author Response: ...'see the _exptl_special_details item'

Alert level B
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for        C3B
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for        C7B
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        C6B
PLAT331_ALERT_2_B Small Average Phenyl C-C Dist.   C1A    -C6A           1.36 Ang.
PLAT331_ALERT_2_B Small Average Phenyl C-C Dist.   C1B    -C6B           1.35 Ang.
PLAT340_ALERT_3_B Low Bond Precision on C-C bonds (x 1000) Ang ...         14

Alert level C
REFNR01_ALERT_3_C  Ratio of reflections to parameters is < 10 for a
            centrosymmetric structure
            sine(theta)/lambda                0.4968
            Proportion of unique data used    1.0000
            Ratio reflections to parameters   8.6571
PLAT088_ALERT_3_C Poor Data / Parameter Ratio ....................       8.66
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.19 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C7A
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C2B
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C6A
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for       C12A
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C9B
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for       C12B
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for       C17B
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          4

   3 ALERT level A = In general: serious problem
   6 ALERT level B = Potentially serious problem
  11 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

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

---

Computing details

Data collection: Picker Manual (Picker, 1967); cell refinement: Picker Manual; data reduction: DATRDN (Stewart, 1976); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

2-(acetylamino)-N-benzyl-2-(ethylsulfinyl)acetamide

Crystal data

C13H18N2O3S	Z = 4
Mr = 282.35	F(000) = 600
Triclinic, P1	Dx = 1.268 Mg m^−3
a = 10.114 (2) Å	Cu Kα radiation, λ = 1.54178 Å
b = 10.260 (2) Å	Cell parameters from 32 reflections
c = 15.126 (3) Å	θ = 16–38°
α = 78.70 (3)°	µ = 2.00 mm^−1
β = 73.88 (3)°	T = 294 K
γ = 87.45 (3)°	Prism, colorless
V = 1478.6 (6) Å^3	0.31 × 0.11 × 0.09 mm

Data collection

Picker FACS-1 four-circle diffractometer	2057 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.000
Ni filtered radiation monochromator	θmax = 50.0°, θmin = 3.1°
θ/2θ scans	h = −10→0
Absorption correction: ψ scan (North et al., 1968)	k = −10→10
Tmin = 0.765, Tmax = 0.833	l = −15→14
3030 measured reflections	3 standard reflections every 100 reflections
3030 independent reflections	intensity decay: 3.4%

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)] = 0.077	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.188	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.063P)^2 + 2.4793P] where P = (Fo^2 + 2Fc^2)/3
3030 reflections	(Δ/σ)max = 0.001
350 parameters	Δρmax = 0.34 e Å^−3
0 restraints	Δρmin = −0.31 e Å^−3

Special details

Experimental. No observed reflections above θ = 50°

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
C1A	0.8854 (8)	0.3220 (8)	1.0548 (7)	0.090 (2)
H1A	0.8612	0.3943	1.0149	0.121 (8)*
C2A	0.9390 (11)	0.3417 (11)	1.1256 (9)	0.117 (3)
H2A	0.9521	0.4280	1.1323	0.121 (8)*
C3A	0.9724 (10)	0.2406 (16)	1.1842 (7)	0.117 (3)
H3A	1.0059	0.2557	1.2327	0.121 (8)*
C4A	0.9570 (9)	0.1134 (12)	1.1728 (7)	0.109 (3)
H4A	0.9822	0.0415	1.2125	0.121 (8)*
C5A	0.9039 (7)	0.0929 (8)	1.1019 (6)	0.081 (2)
H5A	0.8928	0.0066	1.0942	0.121 (8)*
C6A	0.8680 (6)	0.1967 (7)	1.0435 (5)	0.0614 (18)
C7A	0.8085 (7)	0.1755 (8)	0.9657 (6)	0.085 (2)
H7A1	0.8222	0.0835	0.9585	0.082 (7)*
H7A2	0.7101	0.1903	0.9844	0.082 (7)*
N8A	0.8668 (5)	0.2597 (6)	0.8766 (4)	0.0766 (17)
H8A	0.9545	0.2721	0.8590	0.121 (8)*
C9A	0.7947 (7)	0.3196 (6)	0.8197 (5)	0.0632 (18)
C10A	0.8772 (6)	0.3981 (7)	0.7293 (4)	0.0632 (18)
H10A	0.9518	0.4423	0.7422	0.082 (7)*
N11A	0.8005 (5)	0.4981 (5)	0.6867 (4)	0.0703 (16)
H11A	0.7144	0.4849	0.6942	0.121 (8)*
C12A	0.8606 (9)	0.6145 (8)	0.6342 (5)	0.079 (2)
C13A	0.7693 (9)	0.7113 (8)	0.5931 (6)	0.104 (3)
H13A	0.8141	0.7445	0.5282	0.142 (10)*
H13B	0.7503	0.7838	0.6262	0.142 (10)*
H13C	0.6845	0.6678	0.5984	0.142 (10)*
O14A	0.6685 (4)	0.3083 (5)	0.8372 (3)	0.0811 (14)
S15A	0.95709 (17)	0.29148 (19)	0.64263 (14)	0.0762 (6)
O16A	1.0413 (5)	0.1942 (5)	0.6871 (4)	0.1002 (17)
C17A	0.8100 (6)	0.2014 (7)	0.6422 (6)	0.084 (2)
H17A	0.7630	0.1585	0.7056	0.082 (7)*
H17B	0.7464	0.2621	0.6180	0.082 (7)*
C18A	0.8548 (8)	0.0990 (8)	0.5821 (6)	0.108 (3)
H18A	0.9053	0.1415	0.5202	0.142 (10)*
H18B	0.7754	0.0544	0.5789	0.142 (10)*
H18C	0.9126	0.0356	0.6088	0.142 (10)*
O19A	0.9815 (6)	0.6365 (6)	0.6237 (4)	0.115 (2)
C1B	0.3840 (9)	0.1414 (11)	1.0628 (8)	0.105 (3)
H1B	0.3572	0.0895	1.0267	0.121 (8)*
C2B	0.4428 (16)	0.0841 (13)	1.1310 (11)	0.160 (6)
H2B	0.4521	−0.0078	1.1423	0.121 (8)*
C3B	0.4875 (15)	0.153 (2)	1.1821 (9)	0.181 (9)
H3B	0.5269	0.1115	1.2288	0.121 (8)*
C4B	0.4745 (11)	0.2862 (16)	1.1650 (8)	0.129 (4)
H4B	0.5078	0.3373	1.1987	0.121 (8)*
C5B	0.4123 (8)	0.3470 (8)	1.0978 (6)	0.091 (2)
H5B	0.4026	0.4388	1.0864	0.121 (8)*
C6B	0.3647 (6)	0.2714 (8)	1.0477 (5)	0.0657 (19)
C7B	0.2996 (8)	0.3370 (10)	0.9737 (6)	0.108 (3)
H7B1	0.2039	0.3091	0.9920	0.082 (7)*
H7B2	0.3017	0.4324	0.9698	0.082 (7)*
N8B	0.3653 (5)	0.3079 (6)	0.8821 (4)	0.0818 (18)
H8B	0.4537	0.3055	0.8645	0.121 (8)*
C9B	0.2966 (7)	0.2846 (6)	0.8235 (5)	0.0572 (17)
C10B	0.3866 (6)	0.2633 (6)	0.7307 (4)	0.0606 (17)
H10B	0.4691	0.2167	0.7414	0.082 (7)*
N11B	0.3201 (5)	0.1823 (5)	0.6873 (4)	0.0675 (15)
H11B	0.2322	0.1857	0.6968	0.121 (8)*
C12B	0.3940 (8)	0.1012 (7)	0.6316 (5)	0.0671 (19)
C13B	0.3136 (7)	0.0177 (7)	0.5949 (6)	0.090 (2)
H13D	0.3549	0.0227	0.5290	0.142 (10)*
H13E	0.2208	0.0492	0.6049	0.142 (10)*
H13F	0.3131	−0.0729	0.6270	0.142 (10)*
O14B	0.1714 (4)	0.2816 (5)	0.8416 (3)	0.0761 (14)
S15B	0.44232 (18)	0.42175 (19)	0.64779 (15)	0.0838 (7)
O16B	0.5218 (5)	0.4936 (5)	0.6899 (5)	0.133 (2)
C17B	0.2847 (7)	0.5059 (7)	0.6527 (6)	0.085 (2)
H17C	0.2279	0.4590	0.6267	0.082 (7)*
H17D	0.2359	0.5070	0.7175	0.082 (7)*
C18B	0.3092 (8)	0.6442 (9)	0.5993 (7)	0.121 (3)
H18D	0.3665	0.6902	0.6245	0.142 (10)*
H18E	0.2228	0.6890	0.6042	0.142 (10)*
H18F	0.3542	0.6430	0.5346	0.142 (10)*
O19B	0.5192 (5)	0.0977 (5)	0.6165 (4)	0.0934 (17)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1A	0.085 (6)	0.074 (6)	0.095 (7)	0.009 (4)	−0.004 (5)	−0.013 (5)
C2A	0.131 (9)	0.106 (8)	0.100 (9)	−0.025 (7)	0.003 (7)	−0.035 (7)
C3A	0.110 (7)	0.177 (12)	0.060 (7)	−0.035 (8)	−0.011 (5)	−0.028 (8)
C4A	0.096 (7)	0.139 (10)	0.082 (7)	0.005 (6)	−0.031 (5)	0.007 (6)
C5A	0.074 (5)	0.079 (6)	0.080 (6)	0.007 (4)	−0.014 (5)	0.000 (5)
C6A	0.043 (4)	0.062 (5)	0.071 (5)	−0.002 (3)	−0.010 (4)	0.001 (4)
C7A	0.058 (4)	0.099 (6)	0.096 (7)	−0.005 (4)	−0.026 (5)	−0.002 (5)
N8A	0.046 (3)	0.107 (5)	0.072 (4)	−0.012 (3)	−0.018 (3)	0.000 (4)
C9A	0.051 (5)	0.072 (5)	0.075 (5)	0.004 (4)	−0.022 (4)	−0.028 (4)
C10A	0.044 (4)	0.082 (5)	0.061 (5)	−0.010 (4)	−0.007 (4)	−0.017 (4)
N11A	0.059 (3)	0.062 (4)	0.087 (4)	−0.003 (3)	−0.022 (3)	−0.004 (3)
C12A	0.080 (6)	0.082 (6)	0.075 (6)	0.001 (5)	−0.021 (5)	−0.015 (5)
C13A	0.103 (6)	0.087 (6)	0.116 (7)	−0.006 (5)	−0.033 (6)	0.001 (5)
O14A	0.032 (3)	0.115 (4)	0.094 (4)	−0.001 (2)	−0.016 (2)	−0.014 (3)
S15A	0.0471 (10)	0.0989 (15)	0.0872 (15)	−0.0006 (9)	−0.0152 (10)	−0.0327 (11)
O16A	0.064 (3)	0.119 (4)	0.146 (5)	0.031 (3)	−0.060 (3)	−0.055 (4)
C17A	0.046 (4)	0.114 (6)	0.115 (6)	0.009 (4)	−0.035 (4)	−0.054 (5)
C18A	0.075 (5)	0.116 (7)	0.161 (9)	0.014 (5)	−0.048 (6)	−0.076 (7)
O19A	0.069 (4)	0.138 (5)	0.129 (5)	−0.037 (3)	−0.026 (3)	0.004 (4)
C1B	0.110 (7)	0.082 (7)	0.120 (9)	−0.028 (5)	−0.012 (6)	−0.030 (6)
C2B	0.204 (15)	0.104 (9)	0.116 (12)	0.024 (9)	0.011 (10)	0.030 (9)
C3B	0.162 (12)	0.30 (2)	0.063 (8)	0.086 (15)	−0.035 (8)	−0.001 (12)
C4B	0.099 (8)	0.210 (13)	0.092 (9)	−0.020 (8)	−0.031 (6)	−0.051 (9)
C5B	0.097 (6)	0.089 (6)	0.095 (7)	−0.003 (5)	−0.028 (5)	−0.028 (5)
C6B	0.048 (4)	0.080 (6)	0.081 (5)	0.005 (4)	−0.021 (4)	−0.040 (5)
C7B	0.069 (5)	0.170 (9)	0.111 (7)	0.046 (5)	−0.039 (5)	−0.077 (7)
N8B	0.044 (3)	0.133 (5)	0.080 (4)	0.012 (3)	−0.019 (3)	−0.046 (4)
C9B	0.042 (4)	0.071 (4)	0.064 (5)	−0.003 (3)	−0.019 (4)	−0.017 (3)
C10B	0.051 (4)	0.068 (4)	0.059 (5)	0.005 (3)	−0.010 (4)	−0.011 (4)
N11B	0.053 (3)	0.078 (4)	0.080 (4)	0.004 (3)	−0.019 (3)	−0.033 (3)
C12B	0.067 (5)	0.072 (5)	0.072 (5)	0.006 (4)	−0.032 (4)	−0.019 (4)
C13B	0.084 (5)	0.090 (5)	0.113 (7)	0.016 (4)	−0.037 (5)	−0.049 (5)
O14B	0.030 (3)	0.117 (4)	0.085 (3)	−0.003 (2)	−0.015 (2)	−0.030 (3)
S15B	0.0497 (11)	0.0825 (14)	0.1080 (17)	0.0001 (9)	−0.0115 (10)	−0.0063 (11)
O16B	0.085 (4)	0.103 (4)	0.225 (7)	−0.020 (3)	−0.089 (5)	0.008 (4)
C17B	0.051 (4)	0.079 (5)	0.118 (7)	0.004 (4)	−0.026 (4)	0.002 (5)
C18B	0.074 (5)	0.109 (7)	0.160 (9)	0.015 (5)	−0.026 (6)	0.011 (7)
O19B	0.052 (3)	0.126 (4)	0.111 (4)	0.012 (3)	−0.017 (3)	−0.054 (3)

Geometric parameters (Å, º)

C1A—C6A	1.354 (10)	C1B—C6B	1.323 (11)
C1A—C2A	1.379 (12)	C1B—C2B	1.356 (15)
C1A—H1A	0.9300	C1B—H1B	0.9300
C2A—C3A	1.323 (13)	C2B—C3B	1.327 (18)
C2A—H2A	0.9300	C2B—H2B	0.9300
C3A—C4A	1.372 (13)	C3B—C4B	1.338 (18)
C3A—H3A	0.9300	C3B—H3B	0.9300
C4A—C5A	1.379 (11)	C4B—C5B	1.375 (13)
C4A—H4A	0.9300	C4B—H4B	0.9300
C5A—C6A	1.349 (9)	C5B—C6B	1.368 (10)
C5A—H5A	0.9300	C5B—H5B	0.9300
C6A—C7A	1.516 (9)	C6B—C7B	1.488 (10)
C7A—N8A	1.436 (8)	C7B—N8B	1.443 (9)
C7A—H7A1	0.9700	C7B—H7B1	0.9700
C7A—H7A2	0.9700	C7B—H7B2	0.9700
N8A—C9A	1.324 (8)	N8B—C9B	1.328 (7)
N8A—H8A	0.8600	N8B—H8B	0.8600
C9A—O14A	1.236 (7)	C9B—O14B	1.219 (7)
C9A—C10A	1.485 (9)	C9B—C10B	1.497 (8)
C10A—N11A	1.421 (8)	C10B—N11B	1.444 (8)
C10A—S15A	1.860 (6)	C10B—S15B	1.850 (6)
C10A—H10A	0.9800	C10B—H10B	0.9800
N11A—C12A	1.359 (9)	N11B—C12B	1.352 (8)
N11A—H11A	0.8600	N11B—H11B	0.8600
C12A—O19A	1.214 (8)	C12B—O19B	1.223 (7)
C12A—C13A	1.492 (10)	C12B—C13B	1.486 (9)
C13A—H13A	0.9600	C13B—H13D	0.9600
C13A—H13B	0.9600	C13B—H13E	0.9600
C13A—H13C	0.9600	C13B—H13F	0.9600
S15A—O16A	1.467 (5)	S15B—O16B	1.455 (6)
S15A—C17A	1.788 (6)	S15B—C17B	1.769 (6)
C17A—C18A	1.495 (9)	C17B—C18B	1.484 (10)
C17A—H17A	0.9700	C17B—H17C	0.9700
C17A—H17B	0.9700	C17B—H17D	0.9700
C18A—H18A	0.9600	C18B—H18D	0.9600
C18A—H18B	0.9600	C18B—H18E	0.9600
C18A—H18C	0.9600	C18B—H18F	0.9600
C6A—C1A—C2A	119.8 (8)	C6B—C1B—C2B	119.9 (10)
C6A—C1A—H1A	120.1	C6B—C1B—H1B	120.1
C2A—C1A—H1A	120.1	C2B—C1B—H1B	120.1
C3A—C2A—C1A	121.4 (10)	C3B—C2B—C1B	122.4 (14)
C3A—C2A—H2A	119.3	C3B—C2B—H2B	118.8
C1A—C2A—H2A	119.3	C1B—C2B—H2B	118.8
C2A—C3A—C4A	119.4 (10)	C4B—C3B—C2B	118.6 (14)
C2A—C3A—H3A	120.3	C4B—C3B—H3B	120.7
C4A—C3A—H3A	120.3	C2B—C3B—H3B	120.7
C3A—C4A—C5A	119.5 (9)	C3B—C4B—C5B	120.3 (12)
C3A—C4A—H4A	120.3	C3B—C4B—H4B	119.9
C5A—C4A—H4A	120.3	C5B—C4B—H4B	119.9
C6A—C5A—C4A	120.6 (8)	C4B—C5B—C6B	119.6 (9)
C6A—C5A—H5A	119.7	C4B—C5B—H5B	120.2
C4A—C5A—H5A	119.7	C6B—C5B—H5B	120.2
C5A—C6A—C1A	119.3 (8)	C1B—C6B—C5B	119.2 (8)
C5A—C6A—C7A	121.1 (7)	C1B—C6B—C7B	120.9 (8)
C1A—C6A—C7A	119.5 (7)	C5B—C6B—C7B	119.8 (8)
N8A—C7A—C6A	114.6 (6)	N8B—C7B—C6B	113.9 (6)
N8A—C7A—H7A1	108.6	N8B—C7B—H7B1	108.8
C6A—C7A—H7A1	108.6	C6B—C7B—H7B1	108.8
N8A—C7A—H7A2	108.6	N8B—C7B—H7B2	108.8
C6A—C7A—H7A2	108.6	C6B—C7B—H7B2	108.8
H7A1—C7A—H7A2	107.6	H7B1—C7B—H7B2	107.7
C9A—N8A—C7A	124.5 (6)	C9B—N8B—C7B	123.5 (6)
C9A—N8A—H8A	117.8	C9B—N8B—H8B	118.3
C7A—N8A—H8A	117.8	C7B—N8B—H8B	118.3
O14A—C9A—N8A	123.4 (7)	O14B—C9B—N8B	124.3 (6)
O14A—C9A—C10A	121.3 (6)	O14B—C9B—C10B	121.6 (6)
N8A—C9A—C10A	115.2 (6)	N8B—C9B—C10B	114.0 (6)
N11A—C10A—C9A	113.4 (5)	N11B—C10B—C9B	112.3 (5)
N11A—C10A—S15A	108.1 (4)	N11B—C10B—S15B	108.5 (4)
C9A—C10A—S15A	112.4 (5)	C9B—C10B—S15B	112.3 (4)
N11A—C10A—H10A	107.6	N11B—C10B—H10B	107.9
C9A—C10A—H10A	107.6	C9B—C10B—H10B	107.9
S15A—C10A—H10A	107.6	S15B—C10B—H10B	107.9
C12A—N11A—C10A	121.3 (6)	C12B—N11B—C10B	120.9 (5)
C12A—N11A—H11A	119.3	C12B—N11B—H11B	119.5
C10A—N11A—H11A	119.3	C10B—N11B—H11B	119.5
O19A—C12A—N11A	120.7 (7)	O19B—C12B—N11B	119.8 (6)
O19A—C12A—C13A	123.1 (8)	O19B—C12B—C13B	124.2 (7)
N11A—C12A—C13A	116.2 (7)	N11B—C12B—C13B	116.0 (6)
C12A—C13A—H13A	109.5	C12B—C13B—H13D	109.5
C12A—C13A—H13B	109.5	C12B—C13B—H13E	109.5
H13A—C13A—H13B	109.5	H13D—C13B—H13E	109.5
C12A—C13A—H13C	109.5	C12B—C13B—H13F	109.5
H13A—C13A—H13C	109.5	H13D—C13B—H13F	109.5
H13B—C13A—H13C	109.5	H13E—C13B—H13F	109.5
O16A—S15A—C17A	105.9 (3)	O16B—S15B—C17B	107.3 (4)
O16A—S15A—C10A	106.5 (3)	O16B—S15B—C10B	106.7 (3)
C17A—S15A—C10A	101.0 (3)	C17B—S15B—C10B	102.3 (3)
C18A—C17A—S15A	109.5 (5)	C18B—C17B—S15B	110.7 (5)
C18A—C17A—H17A	109.8	C18B—C17B—H17C	109.5
S15A—C17A—H17A	109.8	S15B—C17B—H17C	109.5
C18A—C17A—H17B	109.8	C18B—C17B—H17D	109.5
S15A—C17A—H17B	109.8	S15B—C17B—H17D	109.5
H17A—C17A—H17B	108.2	H17C—C17B—H17D	108.1
C17A—C18A—H18A	109.5	C17B—C18B—H18D	109.5
C17A—C18A—H18B	109.5	C17B—C18B—H18E	109.5
H18A—C18A—H18B	109.5	H18D—C18B—H18E	109.5
C17A—C18A—H18C	109.5	C17B—C18B—H18F	109.5
H18A—C18A—H18C	109.5	H18D—C18B—H18F	109.5
H18B—C18A—H18C	109.5	H18E—C18B—H18F	109.5
C6A—C1A—C2A—C3A	−1.0 (14)	C6B—C1B—C2B—C3B	−2.6 (19)
C1A—C2A—C3A—C4A	1.8 (15)	C1B—C2B—C3B—C4B	0 (2)
C2A—C3A—C4A—C5A	−1.5 (14)	C2B—C3B—C4B—C5B	2 (2)
C3A—C4A—C5A—C6A	0.4 (12)	C3B—C4B—C5B—C6B	−0.3 (16)
C4A—C5A—C6A—C1A	0.4 (10)	C2B—C1B—C6B—C5B	3.8 (13)
C4A—C5A—C6A—C7A	−179.5 (7)	C2B—C1B—C6B—C7B	−179.6 (9)
C2A—C1A—C6A—C5A	−0.1 (11)	C4B—C5B—C6B—C1B	−2.4 (12)
C2A—C1A—C6A—C7A	179.7 (7)	C4B—C5B—C6B—C7B	−179.1 (8)
C5A—C6A—C7A—N8A	−134.4 (7)	C1B—C6B—C7B—N8B	−53.9 (11)
C1A—C6A—C7A—N8A	45.7 (9)	C5B—C6B—C7B—N8B	122.7 (8)
C6A—C7A—N8A—C9A	−137.7 (7)	C6B—C7B—N8B—C9B	139.6 (7)
C7A—N8A—C9A—O14A	−0.6 (11)	C7B—N8B—C9B—O14B	−2.1 (11)
C7A—N8A—C9A—C10A	−177.7 (6)	C7B—N8B—C9B—C10B	177.3 (7)
O14A—C9A—C10A—N11A	25.2 (9)	O14B—C9B—C10B—N11B	−26.9 (8)
N8A—C9A—C10A—N11A	−157.6 (6)	N8B—C9B—C10B—N11B	153.6 (6)
O14A—C9A—C10A—S15A	−97.7 (6)	O14B—C9B—C10B—S15B	95.6 (6)
N8A—C9A—C10A—S15A	79.5 (6)	N8B—C9B—C10B—S15B	−83.8 (6)
C9A—C10A—N11A—C12A	147.9 (6)	C9B—C10B—N11B—C12B	−148.5 (6)
S15A—C10A—N11A—C12A	−86.9 (7)	S15B—C10B—N11B—C12B	86.9 (6)
C10A—N11A—C12A—O19A	−1.2 (11)	C10B—N11B—C12B—O19B	−1.1 (10)
C10A—N11A—C12A—C13A	179.8 (6)	C10B—N11B—C12B—C13B	176.8 (6)
N11A—C10A—S15A—O16A	176.9 (4)	N11B—C10B—S15B—O16B	−173.8 (4)
C9A—C10A—S15A—O16A	−57.2 (5)	C9B—C10B—S15B—O16B	61.6 (5)
N11A—C10A—S15A—C17A	−72.7 (5)	N11B—C10B—S15B—C17B	73.7 (5)
C9A—C10A—S15A—C17A	53.2 (6)	C9B—C10B—S15B—C17B	−50.9 (6)
O16A—S15A—C17A—C18A	−63.9 (7)	O16B—S15B—C17B—C18B	60.7 (7)
C10A—S15A—C17A—C18A	−174.7 (6)	C10B—S15B—C17B—C18B	172.8 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N8A—H8A···O14B^i	0.86	2.14	2.988 (7)	169
N8B—H8B···O14A	0.86	2.10	2.952 (7)	173
N11A—H11A···O16B	0.86	1.96	2.808 (7)	167
N11B—H11B···O16A^ii	0.86	1.97	2.818 (7)	167
C4A—H4A···O16A^iii	0.93	2.57	3.442 (12)	156
C4B—H4B···O16B^iv	0.93	2.60	3.453 (14)	153
C10A—H10A···O19A	0.98	2.37	2.723 (8)	100
C13A—H13C···O16B	0.96	2.42	3.252 (10)	145
C13B—H13E···O16A^ii	0.96	2.51	3.351 (8)	147
C18A—H18B···O19B	0.96	2.53	3.289 (9)	136
C18B—H18E···O19A^ii	0.96	2.45	3.235 (10)	139
C7B—H7B1···O14B	0.97	2.46	2.819 (9)	102
C7A—H7A2···O14A	0.97	2.45	2.821 (9)	102

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