N-Cyclo-hexyl-N-ethyl-benzene-sulfonamide.

The title compound, C(14)H(21)NO(2)S, synthesized by N-methyl-ation of cyclo-hexyl-amine sulfonamide with ethyl iodide is of inter-est as a precursor to biologically active sulfur-containing heterocyclic compounds. There are two independent mol-ecules in the asymmetric unit. The dihedral angles between the mean planes of the phenyl ring and the cyclo-hexyl ring are 40.29 (11) and 37.91 (13)° in the two mol-ecules.

Related literature

For the synthesis of related mol­ecules, see: Arshad et al. (2009 ▶); Zia-ur-Rehman et al. (2009 ▶). For the biological activity of sulfonamides, see: Berredjem et al. (2000 ▶); Lee & Lee (2002 ▶); Soledade et al. (2006 ▶); Xiao & Timberlake (2000 ▶).

Experimental

Crystal data

C14H21NO2S

M = 267.38

Monoclinic,

a = 18.195 (1) Å

b = 12.9799 (7) Å

c = 12.7327 (6) Å

β = 108.587 (3)°

V = 2850.2 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.22 mm−1

T = 296 K

0.42 × 0.11 × 0.08 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: none

32427 measured reflections

7061 independent reflections

3979 reflections with I > 2σ(I)

R int = 0.056

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.148

S = 0.99

7061 reflections

327 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶) and local programs.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809044006/bt5111sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809044006/bt5111Isup2.hkl

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

C14H21NO2S	F(000) = 1152
Mr = 267.38	Dx = 1.246 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3394 reflections
a = 18.195 (1) Å	θ = 2.3–21.8°
b = 12.9799 (7) Å	µ = 0.22 mm−1
c = 12.7327 (6) Å	T = 296 K
β = 108.587 (3)°	Needles, colourless
V = 2850.2 (3) Å3	0.42 × 0.11 × 0.08 mm
Z = 8

Bruker APEXII CCD area-detector diffractometer	3979 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.056
graphite	θmax = 28.3°, θmin = 1.2°
φ and ω scans	h = −24→23
32427 measured reflections	k = −17→16
7061 independent reflections	l = −16→17

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.148	H-atom parameters constrained
S = 0.99	w = 1/[σ2(Fo2) + (0.0572P)2 + 0.5289P] where P = (Fo2 + 2Fc2)/3
7061 reflections	(Δ/σ)max < 0.001
327 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
S1	0.36993 (4)	0.68047 (5)	0.03599 (5)	0.0533 (2)
O1	0.39686 (11)	0.64718 (16)	−0.05209 (14)	0.0755 (6)
O2	0.37154 (11)	0.78735 (14)	0.06200 (17)	0.0710 (6)
N1	0.28139 (11)	0.64066 (15)	0.00768 (15)	0.0464 (5)
C1	0.42614 (14)	0.61647 (19)	0.1568 (2)	0.0473 (6)
C2	0.46699 (15)	0.5285 (2)	0.1493 (2)	0.0574 (7)
H2	0.4652	0.5029	0.0803	0.069*
C3	0.51032 (18)	0.4790 (2)	0.2447 (3)	0.0751 (9)
H3	0.5381	0.4200	0.2401	0.090*
C4	0.5126 (2)	0.5163 (3)	0.3462 (3)	0.0848 (11)
H4	0.5420	0.4826	0.4103	0.102*
C5	0.47221 (19)	0.6025 (3)	0.3537 (2)	0.0793 (10)
H5	0.4737	0.6270	0.4230	0.095*
C6	0.42914 (16)	0.6539 (2)	0.2599 (2)	0.0614 (7)
H6	0.4022	0.7133	0.2657	0.074*
C7	0.23333 (13)	0.68049 (18)	0.07358 (17)	0.0409 (6)
H7	0.2614	0.7389	0.1167	0.049*
C8	0.15687 (14)	0.7218 (2)	−0.00157 (19)	0.0529 (7)
H8A	0.1276	0.6663	−0.0470	0.063*
H8B	0.1666	0.7735	−0.0505	0.063*
C9	0.10942 (16)	0.7692 (2)	0.0651 (2)	0.0637 (8)
H9A	0.1357	0.8302	0.1029	0.076*
H9B	0.0593	0.7902	0.0151	0.076*
C10	0.09773 (17)	0.6946 (2)	0.1492 (2)	0.0725 (9)
H10A	0.0714	0.7294	0.1944	0.087*
H10B	0.0650	0.6383	0.1110	0.087*
C11	0.17359 (17)	0.6522 (2)	0.2226 (2)	0.0701 (8)
H11A	0.1637	0.6011	0.2719	0.084*
H11B	0.2036	0.7074	0.2677	0.084*
C12	0.22025 (15)	0.6035 (2)	0.1559 (2)	0.0572 (7)
H12A	0.1928	0.5439	0.1164	0.069*
H12B	0.2699	0.5805	0.2056	0.069*
C13	0.26176 (16)	0.5405 (2)	−0.0484 (2)	0.0591 (7)
H13A	0.2257	0.5049	−0.0191	0.071*
H13B	0.3084	0.4990	−0.0317	0.071*
C14	0.2265 (2)	0.5491 (3)	−0.1719 (2)	0.0908 (11)
H14A	0.1821	0.5936	−0.1892	0.136*
H14B	0.2109	0.4821	−0.2028	0.136*
H14C	0.2640	0.5773	−0.2026	0.136*
S2	0.14463 (4)	0.28954 (5)	0.47894 (6)	0.0536 (2)
O3	0.12606 (12)	0.31641 (16)	0.57629 (15)	0.0769 (6)
O4	0.13794 (11)	0.18488 (13)	0.44305 (17)	0.0707 (6)
N2	0.23252 (11)	0.32654 (14)	0.49770 (15)	0.0455 (5)
C15	0.08332 (14)	0.36211 (19)	0.3684 (2)	0.0501 (6)
C16	0.07673 (16)	0.3370 (2)	0.2607 (2)	0.0635 (8)
H16	0.1030	0.2803	0.2456	0.076*
C17	0.03073 (18)	0.3967 (3)	0.1753 (3)	0.0799 (9)
H17	0.0267	0.3809	0.1024	0.096*
C18	−0.00889 (18)	0.4787 (3)	0.1970 (3)	0.0850 (10)
H18	−0.0405	0.5181	0.1391	0.102*
C19	−0.00210 (19)	0.5031 (3)	0.3045 (3)	0.0829 (10)
H19	−0.0291	0.5592	0.3192	0.099*
C20	0.04401 (17)	0.4456 (2)	0.3902 (3)	0.0670 (8)
H20	0.0488	0.4628	0.4630	0.080*
C21	0.27320 (13)	0.29122 (17)	0.42041 (17)	0.0398 (6)
H21	0.2384	0.2427	0.3690	0.048*
C22	0.29029 (15)	0.37719 (19)	0.35061 (19)	0.0498 (6)
H22A	0.2425	0.4123	0.3108	0.060*
H22B	0.3250	0.4269	0.3985	0.060*
C23	0.32733 (15)	0.3341 (2)	0.26870 (19)	0.0547 (7)
H23A	0.2902	0.2905	0.2157	0.066*
H23B	0.3408	0.3904	0.2282	0.066*
C24	0.39939 (15)	0.2723 (2)	0.3260 (2)	0.0601 (7)
H24A	0.4185	0.2408	0.2706	0.072*
H24B	0.4393	0.3181	0.3705	0.072*
C25	0.38391 (16)	0.1893 (2)	0.3992 (2)	0.0574 (7)
H25A	0.4324	0.1561	0.4398	0.069*
H25B	0.3501	0.1375	0.3533	0.069*
C26	0.34638 (14)	0.23229 (19)	0.48063 (19)	0.0489 (6)
H26A	0.3338	0.1762	0.5223	0.059*
H26B	0.3826	0.2777	0.5325	0.059*
C27	0.26849 (18)	0.4076 (2)	0.5788 (2)	0.0659 (8)
H27A	0.3243	0.4032	0.5960	0.079*
H27B	0.2567	0.3936	0.6466	0.079*
C28	0.2440 (2)	0.5137 (2)	0.5434 (3)	0.0844 (10)
H28A	0.2526	0.5275	0.4742	0.127*
H28B	0.2736	0.5613	0.5985	0.127*
H28C	0.1899	0.5215	0.5346	0.127*

	U11	U22	U33	U12	U13	U23
S1	0.0519 (4)	0.0526 (4)	0.0639 (4)	0.0001 (3)	0.0304 (3)	0.0080 (3)
O1	0.0719 (14)	0.1040 (16)	0.0669 (12)	0.0096 (12)	0.0452 (10)	0.0145 (11)
O2	0.0605 (13)	0.0438 (11)	0.1111 (15)	−0.0072 (10)	0.0307 (11)	0.0086 (10)
N1	0.0459 (13)	0.0466 (13)	0.0501 (11)	−0.0015 (10)	0.0200 (9)	−0.0048 (9)
C1	0.0412 (15)	0.0473 (16)	0.0577 (15)	−0.0071 (13)	0.0218 (12)	−0.0012 (12)
C2	0.0539 (18)	0.0514 (17)	0.0708 (18)	−0.0053 (15)	0.0256 (15)	0.0023 (14)
C3	0.059 (2)	0.062 (2)	0.106 (3)	0.0033 (16)	0.0268 (18)	0.0164 (19)
C4	0.064 (2)	0.096 (3)	0.082 (2)	−0.021 (2)	0.0061 (18)	0.029 (2)
C5	0.072 (2)	0.099 (3)	0.0605 (19)	−0.024 (2)	0.0135 (17)	0.0000 (19)
C6	0.0545 (18)	0.0647 (19)	0.0678 (18)	−0.0144 (15)	0.0236 (15)	−0.0111 (15)
C7	0.0436 (14)	0.0394 (14)	0.0427 (12)	−0.0033 (11)	0.0179 (11)	−0.0017 (10)
C8	0.0531 (16)	0.0558 (17)	0.0501 (13)	0.0040 (14)	0.0168 (12)	0.0076 (12)
C9	0.0546 (18)	0.070 (2)	0.0715 (17)	0.0138 (15)	0.0270 (14)	0.0101 (15)
C10	0.061 (2)	0.086 (2)	0.084 (2)	0.0137 (17)	0.0427 (16)	0.0132 (17)
C11	0.081 (2)	0.079 (2)	0.0640 (17)	0.0060 (18)	0.0433 (16)	0.0147 (15)
C12	0.0603 (18)	0.0580 (17)	0.0589 (15)	0.0040 (15)	0.0268 (13)	0.0149 (13)
C13	0.0666 (19)	0.0513 (17)	0.0613 (16)	0.0017 (14)	0.0228 (14)	−0.0094 (13)
C14	0.109 (3)	0.096 (3)	0.0632 (19)	0.005 (2)	0.0218 (18)	−0.0250 (18)
S2	0.0558 (4)	0.0487 (4)	0.0696 (4)	−0.0011 (3)	0.0386 (3)	0.0054 (3)
O3	0.0871 (15)	0.0920 (15)	0.0755 (12)	0.0103 (12)	0.0596 (11)	0.0152 (11)
O4	0.0642 (13)	0.0413 (11)	0.1158 (15)	−0.0094 (10)	0.0415 (11)	0.0017 (10)
N2	0.0521 (13)	0.0427 (12)	0.0492 (11)	−0.0066 (10)	0.0267 (9)	−0.0077 (9)
C15	0.0408 (15)	0.0497 (16)	0.0676 (16)	−0.0033 (13)	0.0283 (13)	−0.0019 (13)
C16	0.0528 (18)	0.069 (2)	0.0711 (18)	−0.0079 (16)	0.0239 (15)	−0.0120 (16)
C17	0.051 (2)	0.109 (3)	0.071 (2)	−0.010 (2)	0.0067 (16)	0.004 (2)
C18	0.047 (2)	0.083 (3)	0.112 (3)	−0.0060 (19)	0.0077 (19)	0.027 (2)
C19	0.061 (2)	0.067 (2)	0.121 (3)	0.0084 (18)	0.029 (2)	0.000 (2)
C20	0.0582 (19)	0.066 (2)	0.083 (2)	0.0117 (16)	0.0302 (16)	−0.0007 (17)
C21	0.0427 (14)	0.0390 (13)	0.0422 (12)	−0.0044 (11)	0.0197 (10)	−0.0044 (10)
C22	0.0575 (17)	0.0498 (15)	0.0476 (13)	0.0004 (13)	0.0245 (12)	0.0043 (12)
C23	0.0635 (18)	0.0614 (18)	0.0476 (13)	0.0016 (15)	0.0297 (13)	0.0063 (12)
C24	0.0572 (18)	0.0721 (19)	0.0619 (15)	0.0006 (15)	0.0344 (13)	0.0032 (14)
C25	0.0535 (17)	0.0617 (18)	0.0647 (15)	0.0106 (14)	0.0298 (13)	0.0053 (14)
C26	0.0500 (16)	0.0511 (16)	0.0496 (13)	0.0011 (13)	0.0217 (12)	0.0058 (12)
C27	0.085 (2)	0.0609 (19)	0.0617 (16)	−0.0021 (17)	0.0371 (15)	−0.0122 (15)
C28	0.115 (3)	0.060 (2)	0.085 (2)	0.0096 (19)	0.041 (2)	−0.0057 (17)

S1—O2	1.4244 (19)	S2—O4	1.4261 (18)
S1—O1	1.4266 (18)	S2—O3	1.4280 (17)
S1—N1	1.619 (2)	S2—N2	1.613 (2)
S1—C1	1.761 (3)	S2—C15	1.764 (3)
N1—C13	1.472 (3)	N2—C27	1.473 (3)
N1—C7	1.485 (3)	N2—C21	1.480 (3)
C1—C2	1.382 (3)	C15—C20	1.375 (4)
C1—C6	1.384 (3)	C15—C16	1.377 (3)
C2—C3	1.378 (4)	C16—C17	1.379 (4)
C2—H2	0.9300	C16—H16	0.9300
C3—C4	1.368 (4)	C17—C18	1.363 (5)
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.359 (5)	C18—C19	1.371 (5)
C4—H4	0.9300	C18—H18	0.9300
C5—C6	1.374 (4)	C19—C20	1.367 (4)
C5—H5	0.9300	C19—H19	0.9300
C6—H6	0.9300	C20—H20	0.9300
C7—C8	1.513 (3)	C21—C26	1.515 (3)
C7—C12	1.520 (3)	C21—C22	1.519 (3)
C7—H7	0.9800	C21—H21	0.9800
C8—C9	1.520 (3)	C22—C23	1.517 (3)
C8—H8A	0.9700	C22—H22A	0.9700
C8—H8B	0.9700	C22—H22B	0.9700
C9—C10	1.508 (4)	C23—C24	1.512 (4)
C9—H9A	0.9700	C23—H23A	0.9700
C9—H9B	0.9700	C23—H23B	0.9700
C10—C11	1.503 (4)	C24—C25	1.508 (3)
C10—H10A	0.9700	C24—H24A	0.9700
C10—H10B	0.9700	C24—H24B	0.9700
C11—C12	1.517 (3)	C25—C26	1.519 (3)
C11—H11A	0.9700	C25—H25A	0.9700
C11—H11B	0.9700	C25—H25B	0.9700
C12—H12A	0.9700	C26—H26A	0.9700
C12—H12B	0.9700	C26—H26B	0.9700
C13—C14	1.501 (4)	C27—C28	1.474 (4)
C13—H13A	0.9700	C27—H27A	0.9700
C13—H13B	0.9700	C27—H27B	0.9700
C14—H14A	0.9600	C28—H28A	0.9600
C14—H14B	0.9600	C28—H28B	0.9600
C14—H14C	0.9600	C28—H28C	0.9600
O2—S1—O1	119.41 (12)	O4—S2—O3	119.41 (12)
O2—S1—N1	107.93 (11)	O4—S2—N2	108.09 (11)
O1—S1—N1	107.15 (11)	O3—S2—N2	107.24 (11)
O2—S1—C1	107.05 (12)	O4—S2—C15	106.58 (12)
O1—S1—C1	107.14 (12)	O3—S2—C15	107.33 (12)
N1—S1—C1	107.67 (11)	N2—S2—C15	107.70 (11)
C13—N1—C7	119.10 (19)	C27—N2—C21	118.87 (19)
C13—N1—S1	117.41 (17)	C27—N2—S2	120.95 (16)
C7—N1—S1	119.11 (15)	C21—N2—S2	119.45 (15)
C2—C1—C6	119.8 (2)	C20—C15—C16	120.2 (3)
C2—C1—S1	120.3 (2)	C20—C15—S2	119.8 (2)
C6—C1—S1	120.0 (2)	C16—C15—S2	120.0 (2)
C3—C2—C1	119.5 (3)	C15—C16—C17	119.4 (3)
C3—C2—H2	120.3	C15—C16—H16	120.3
C1—C2—H2	120.3	C17—C16—H16	120.3
C4—C3—C2	120.3 (3)	C18—C17—C16	120.4 (3)
C4—C3—H3	119.8	C18—C17—H17	119.8
C2—C3—H3	119.8	C16—C17—H17	119.8
C5—C4—C3	120.2 (3)	C17—C18—C19	119.9 (3)
C5—C4—H4	119.9	C17—C18—H18	120.1
C3—C4—H4	119.9	C19—C18—H18	120.1
C4—C5—C6	120.7 (3)	C20—C19—C18	120.5 (3)
C4—C5—H5	119.7	C20—C19—H19	119.7
C6—C5—H5	119.7	C18—C19—H19	119.7
C5—C6—C1	119.5 (3)	C19—C20—C15	119.7 (3)
C5—C6—H6	120.2	C19—C20—H20	120.2
C1—C6—H6	120.2	C15—C20—H20	120.2
N1—C7—C8	110.77 (18)	N2—C21—C26	111.41 (18)
N1—C7—C12	114.24 (19)	N2—C21—C22	113.61 (19)
C8—C7—C12	110.8 (2)	C26—C21—C22	110.87 (19)
N1—C7—H7	106.9	N2—C21—H21	106.8
C8—C7—H7	106.9	C26—C21—H21	106.8
C12—C7—H7	106.9	C22—C21—H21	106.8
C7—C8—C9	111.2 (2)	C23—C22—C21	110.5 (2)
C7—C8—H8A	109.4	C23—C22—H22A	109.6
C9—C8—H8A	109.4	C21—C22—H22A	109.6
C7—C8—H8B	109.4	C23—C22—H22B	109.6
C9—C8—H8B	109.4	C21—C22—H22B	109.6
H8A—C8—H8B	108.0	H22A—C22—H22B	108.1
C10—C9—C8	111.7 (2)	C24—C23—C22	111.8 (2)
C10—C9—H9A	109.3	C24—C23—H23A	109.3
C8—C9—H9A	109.3	C22—C23—H23A	109.3
C10—C9—H9B	109.3	C24—C23—H23B	109.3
C8—C9—H9B	109.3	C22—C23—H23B	109.3
H9A—C9—H9B	107.9	H23A—C23—H23B	107.9
C11—C10—C9	111.5 (2)	C25—C24—C23	111.9 (2)
C11—C10—H10A	109.3	C25—C24—H24A	109.2
C9—C10—H10A	109.3	C23—C24—H24A	109.2
C11—C10—H10B	109.3	C25—C24—H24B	109.2
C9—C10—H10B	109.3	C23—C24—H24B	109.2
H10A—C10—H10B	108.0	H24A—C24—H24B	107.9
C10—C11—C12	111.8 (2)	C24—C25—C26	111.9 (2)
C10—C11—H11A	109.3	C24—C25—H25A	109.2
C12—C11—H11A	109.3	C26—C25—H25A	109.2
C10—C11—H11B	109.3	C24—C25—H25B	109.2
C12—C11—H11B	109.3	C26—C25—H25B	109.2
H11A—C11—H11B	107.9	H25A—C25—H25B	107.9
C11—C12—C7	110.5 (2)	C21—C26—C25	110.73 (19)
C11—C12—H12A	109.5	C21—C26—H26A	109.5
C7—C12—H12A	109.5	C25—C26—H26A	109.5
C11—C12—H12B	109.5	C21—C26—H26B	109.5
C7—C12—H12B	109.5	C25—C26—H26B	109.5
H12A—C12—H12B	108.1	H26A—C26—H26B	108.1
N1—C13—C14	113.5 (2)	N2—C27—C28	115.4 (2)
N1—C13—H13A	108.9	N2—C27—H27A	108.4
C14—C13—H13A	108.9	C28—C27—H27A	108.4
N1—C13—H13B	108.9	N2—C27—H27B	108.4
C14—C13—H13B	108.9	C28—C27—H27B	108.4
H13A—C13—H13B	107.7	H27A—C27—H27B	107.5
C13—C14—H14A	109.5	C27—C28—H28A	109.5
C13—C14—H14B	109.5	C27—C28—H28B	109.5
H14A—C14—H14B	109.5	H28A—C28—H28B	109.5
C13—C14—H14C	109.5	C27—C28—H28C	109.5
H14A—C14—H14C	109.5	H28A—C28—H28C	109.5
H14B—C14—H14C	109.5	H28B—C28—H28C	109.5
O2—S1—N1—C13	164.91 (17)	O4—S2—N2—C27	−151.80 (18)
O1—S1—N1—C13	35.1 (2)	O3—S2—N2—C27	−21.8 (2)
C1—S1—N1—C13	−79.84 (19)	C15—S2—N2—C27	93.4 (2)
O2—S1—N1—C7	−38.8 (2)	O4—S2—N2—C21	38.1 (2)
O1—S1—N1—C7	−168.55 (16)	O3—S2—N2—C21	168.11 (17)
C1—S1—N1—C7	76.49 (19)	C15—S2—N2—C21	−76.65 (19)
O2—S1—C1—C2	−148.1 (2)	O4—S2—C15—C20	144.5 (2)
O1—S1—C1—C2	−18.9 (2)	O3—S2—C15—C20	15.5 (2)
N1—S1—C1—C2	96.0 (2)	N2—S2—C15—C20	−99.7 (2)
O2—S1—C1—C6	32.3 (2)	O4—S2—C15—C16	−37.5 (2)
O1—S1—C1—C6	161.5 (2)	O3—S2—C15—C16	−166.5 (2)
N1—S1—C1—C6	−83.5 (2)	N2—S2—C15—C16	78.3 (2)
C6—C1—C2—C3	0.0 (4)	C20—C15—C16—C17	0.4 (4)
S1—C1—C2—C3	−179.6 (2)	S2—C15—C16—C17	−177.7 (2)
C1—C2—C3—C4	0.4 (4)	C15—C16—C17—C18	−1.1 (4)
C2—C3—C4—C5	0.0 (5)	C16—C17—C18—C19	1.0 (5)
C3—C4—C5—C6	−0.6 (5)	C17—C18—C19—C20	−0.2 (5)
C4—C5—C6—C1	0.9 (4)	C18—C19—C20—C15	−0.6 (5)
C2—C1—C6—C5	−0.6 (4)	C16—C15—C20—C19	0.5 (4)
S1—C1—C6—C5	179.0 (2)	S2—C15—C20—C19	178.5 (2)
C13—N1—C7—C8	−76.0 (3)	C27—N2—C21—C26	68.9 (3)
S1—N1—C7—C8	128.08 (19)	S2—N2—C21—C26	−120.80 (19)
C13—N1—C7—C12	49.9 (3)	C27—N2—C21—C22	−57.1 (3)
S1—N1—C7—C12	−106.0 (2)	S2—N2—C21—C22	113.1 (2)
N1—C7—C8—C9	−176.3 (2)	N2—C21—C22—C23	−176.43 (19)
C12—C7—C8—C9	55.9 (3)	C26—C21—C22—C23	57.2 (3)
C7—C8—C9—C10	−54.6 (3)	C21—C22—C23—C24	−55.4 (3)
C8—C9—C10—C11	53.9 (3)	C22—C23—C24—C25	53.6 (3)
C9—C10—C11—C12	−54.9 (3)	C23—C24—C25—C26	−53.3 (3)
C10—C11—C12—C7	56.1 (3)	N2—C21—C26—C25	175.45 (19)
N1—C7—C12—C11	177.6 (2)	C22—C21—C26—C25	−57.0 (3)
C8—C7—C12—C11	−56.5 (3)	C24—C25—C26—C21	55.0 (3)
C7—N1—C13—C14	107.4 (3)	C21—N2—C27—C28	93.3 (3)
S1—N1—C13—C14	−96.2 (3)	S2—N2—C27—C28	−76.8 (3)