Phen-yl(1-phenyl-sulfonyl-1H-indol-2-yl)methanone.

The asymmetric unit of the title compound, C(21)H(15)NO(3)S, contains two crystallographically independent mol-ecules. As a result of the electron-withdrawing character of the phenyl-sulfonyl groups, the N-Csp(2) bond lengths are slightly longer than the anti-cipated value of approximately 1.35 Å for N atoms with planar configurations. Both unique S atoms have a distorted tetra-hedral configuration. In each mol-ecule, the indole ring system is essentially planar (r.m.s. deviations for all non-H atoms of 0.020 and 0.023 Å). In one mol-ecule, the indole ring system makes dihedral angles of 65.7 (8) and 73.4 (8)°, respectively, with the benzene and phenyl rings [62.2 (7) and 72.1 (7)°, respectively, in the other mol-ecule].

Related literature

For the biological activity of compounds containing an indole ring system, see: Ma et al. (2001 ▶); Zhou et al. (2006 ▶); Zhao et al. (2002 ▶); Williams et al. (1993 ▶). For related structures, see: Chakkaravarthi et al. (2010 ▶); Kavitha et al. (2010 ▶). For a discussion of the geometry at the N atom, see: Beddoes et al. (1986 ▶). For standard bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C21H15NO3S

M = 361.40

Triclinic,

a = 9.3291 (6) Å

b = 11.1498 (7) Å

c = 17.8134 (10) Å

α = 89.433 (3)°

β = 81.623 (2)°

γ = 71.993 (3)°

V = 1742.13 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.21 mm−1

T = 293 K

0.25 × 0.22 × 0.19 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.981, T max = 0.985

30464 measured reflections

8730 independent reflections

6363 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.138

S = 0.99

8730 reflections

470 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.33 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811008439/nk2081sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811008439/nk2081Isup2.hkl

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

C21H15NO3S	Z = 4
Mr = 361.40	F(000) = 752
Triclinic, P1	Dx = 1.378 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.3291 (6) Å	Cell parameters from 8730 reflections
b = 11.1498 (7) Å	θ = 1.2–28.7°
c = 17.8134 (10) Å	µ = 0.21 mm−1
α = 89.433 (3)°	T = 293 K
β = 81.623 (2)°	Block, white
γ = 71.993 (3)°	0.25 × 0.22 × 0.19 mm
V = 1742.13 (18) Å3

Bruker APEXII CCD area-detector diffractometer	8730 independent reflections
Radiation source: fine-focus sealed tube	6363 reflections with I > 2σ(I)
graphite	Rint = 0.041
ω and φ scans	θmax = 28.7°, θmin = 1.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
Tmin = 0.981, Tmax = 0.985	k = −14→14
30464 measured reflections	l = −23→24

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040	H-atom parameters constrained
wR(F2) = 0.138	w = 1/[σ2(Fo2) + (0.082P)2 + 0.1847P] where P = (Fo2 + 2Fc2)/3
S = 0.99	(Δ/σ)max = 0.001
8730 reflections	Δρmax = 0.27 e Å−3
470 parameters	Δρmin = −0.33 e Å−3
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.085 (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
C1	1.12210 (18)	0.80297 (15)	0.33999 (9)	0.0466 (4)
C1'	1.04606 (17)	0.31674 (14)	0.15061 (8)	0.0427 (3)
C2'	1.1137 (2)	0.19223 (16)	0.16963 (10)	0.0549 (4)
H2'	1.0634	0.1321	0.1694	0.066*
C2	1.1947 (2)	0.67756 (17)	0.31637 (11)	0.0593 (4)
H2	1.1406	0.6201	0.3160	0.071*
C3	1.3500 (2)	0.6420 (2)	0.29356 (11)	0.0679 (5)
H3	1.4015	0.5585	0.2779	0.082*
C3'	1.2583 (2)	0.16248 (19)	0.18871 (10)	0.0620 (5)
H3'	1.3061	0.0802	0.2016	0.074*
C4'	1.3354 (2)	0.25122 (19)	0.18944 (10)	0.0630 (5)
H4'	1.4333	0.2271	0.2022	0.076*
C4	1.4318 (2)	0.7265 (2)	0.29317 (12)	0.0701 (6)
H4	1.5367	0.6987	0.2777	0.084*
C5	1.3603 (2)	0.8508 (2)	0.31527 (11)	0.0621 (5)
H5	1.4157	0.9074	0.3146	0.074*
C5'	1.26861 (18)	0.37364 (18)	0.17157 (10)	0.0559 (4)
H5'	1.3200	0.4330	0.1720	0.067*
C6	1.20280 (18)	0.89080 (16)	0.33877 (9)	0.0486 (4)
C6'	1.12073 (17)	0.40739 (15)	0.15260 (9)	0.0454 (3)
C7	1.09697 (19)	1.00924 (16)	0.36680 (10)	0.0514 (4)
H7	1.1201	1.0840	0.3712	0.062*
C7'	1.02433 (17)	0.52315 (15)	0.12936 (9)	0.0475 (4)
H7'	1.0458	0.5993	0.1265	0.057*
C8'	0.89647 (17)	0.50409 (14)	0.11210 (9)	0.0429 (3)
C8	0.95772 (18)	0.99525 (15)	0.38603 (9)	0.0461 (3)
C9'	0.78298 (17)	0.58882 (14)	0.06981 (9)	0.0439 (3)
C9	0.82428 (18)	1.08384 (16)	0.43345 (9)	0.0493 (4)
C10'	0.74687 (16)	0.72726 (14)	0.08203 (9)	0.0415 (3)
C10	0.79218 (18)	1.22132 (15)	0.42177 (9)	0.0468 (4)
C11	0.72410 (19)	1.30446 (17)	0.48355 (10)	0.0537 (4)
H11	0.7030	1.2735	0.5312	0.064*
C11'	0.74584 (19)	0.78266 (15)	0.15170 (9)	0.0493 (4)
H11'	0.7738	0.7326	0.1925	0.059*
C12'	0.7028 (2)	0.91320 (17)	0.16001 (11)	0.0586 (4)
H12'	0.6983	0.9508	0.2070	0.070*
C12	0.6877 (2)	1.43246 (18)	0.47447 (12)	0.0635 (5)
H12	0.6452	1.4878	0.5163	0.076*
C13	0.7142 (2)	1.47895 (18)	0.40350 (14)	0.0707 (5)
H13	0.6873	1.5656	0.3974	0.085*
C13'	0.6669 (2)	0.98698 (16)	0.09905 (12)	0.0595 (5)
H13'	0.6400	1.0743	0.1047	0.071*
C14'	0.67055 (19)	0.93190 (16)	0.02912 (11)	0.0556 (4)
H14'	0.6486	0.9820	−0.0124	0.067*
C14	0.7801 (3)	1.39750 (19)	0.34158 (13)	0.0721 (6)
H14	0.7972	1.4293	0.2938	0.087*
C15	0.8211 (2)	1.26808 (17)	0.35029 (10)	0.0593 (4)
H15	0.8676	1.2130	0.3087	0.071*
C15'	0.70660 (17)	0.80322 (15)	0.02128 (9)	0.0480 (4)
H15'	0.7041	0.7666	−0.0250	0.058*
C16	0.78168 (17)	0.77029 (15)	0.46542 (9)	0.0460 (3)
C16'	0.76892 (17)	0.26929 (14)	0.03053 (9)	0.0425 (3)
C17'	0.64230 (19)	0.31640 (17)	−0.00556 (10)	0.0525 (4)
H17'	0.5545	0.3754	0.0191	0.063*
C17	0.6358 (2)	0.81398 (18)	0.50410 (11)	0.0604 (4)
H17	0.5582	0.8697	0.4820	0.073*
C18'	0.6491 (2)	0.27381 (19)	−0.07907 (11)	0.0615 (5)
H18'	0.5651	0.3047	−0.1042	0.074*
C18	0.6068 (3)	0.7732 (2)	0.57678 (12)	0.0728 (6)
H18	0.5088	0.8018	0.6039	0.087*
C19	0.7221 (3)	0.6908 (2)	0.60898 (11)	0.0720 (6)
H19	0.7017	0.6646	0.6580	0.086*
C19'	0.7790 (2)	0.18625 (18)	−0.11532 (10)	0.0595 (4)
H19'	0.7826	0.1588	−0.1649	0.071*
C20	0.8674 (2)	0.64670 (19)	0.56934 (12)	0.0674 (5)
H20	0.9447	0.5904	0.5913	0.081*
C20'	0.9040 (2)	0.13900 (17)	−0.07847 (11)	0.0572 (4)
H20'	0.9913	0.0793	−0.1031	0.069*
C21'	0.89966 (18)	0.18017 (15)	−0.00517 (10)	0.0500 (4)
H21'	0.9835	0.1485	0.0200	0.060*
C21	0.8978 (2)	0.68629 (17)	0.49705 (10)	0.0559 (4)
H21	0.9955	0.6568	0.4697	0.067*
N1	0.96883 (15)	0.86837 (12)	0.36984 (7)	0.0467 (3)
N1'	0.90578 (14)	0.37628 (11)	0.12457 (7)	0.0426 (3)
O1'	0.80070 (16)	0.20614 (12)	0.16827 (7)	0.0645 (4)
O1	0.87435 (16)	0.70347 (13)	0.32343 (7)	0.0672 (4)
O2'	0.62388 (13)	0.41561 (13)	0.14936 (7)	0.0630 (3)
O2	0.69510 (15)	0.91680 (14)	0.35443 (8)	0.0673 (4)
O3	0.74722 (15)	1.04506 (12)	0.48283 (7)	0.0645 (3)
O3'	0.72679 (15)	0.54592 (11)	0.02333 (7)	0.0602 (3)
S1'	0.76114 (4)	0.31681 (4)	0.12514 (2)	0.04706 (13)
S1	0.81966 (5)	0.81457 (4)	0.37162 (2)	0.05089 (13)

	U11	U22	U33	U12	U13	U23
C1	0.0480 (8)	0.0498 (8)	0.0411 (8)	−0.0155 (7)	−0.0035 (6)	0.0043 (7)
C1'	0.0429 (8)	0.0457 (8)	0.0392 (7)	−0.0125 (6)	−0.0073 (6)	0.0004 (6)
C2'	0.0607 (10)	0.0490 (9)	0.0533 (10)	−0.0134 (8)	−0.0115 (8)	0.0090 (7)
C2	0.0634 (11)	0.0521 (10)	0.0576 (10)	−0.0154 (8)	0.0006 (8)	−0.0032 (8)
C3	0.0633 (11)	0.0638 (11)	0.0618 (12)	−0.0044 (9)	0.0048 (9)	0.0003 (9)
C3'	0.0611 (11)	0.0620 (11)	0.0512 (10)	−0.0002 (9)	−0.0134 (8)	0.0085 (8)
C4'	0.0468 (9)	0.0795 (13)	0.0536 (10)	−0.0025 (9)	−0.0160 (8)	−0.0050 (9)
C4	0.0478 (10)	0.0844 (14)	0.0652 (12)	−0.0069 (10)	0.0018 (9)	0.0135 (11)
C5	0.0480 (9)	0.0751 (12)	0.0648 (11)	−0.0225 (9)	−0.0077 (8)	0.0190 (10)
C5'	0.0421 (8)	0.0696 (11)	0.0554 (10)	−0.0145 (8)	−0.0109 (7)	−0.0107 (8)
C6	0.0480 (8)	0.0543 (9)	0.0459 (8)	−0.0189 (7)	−0.0093 (7)	0.0106 (7)
C6'	0.0422 (8)	0.0493 (8)	0.0449 (8)	−0.0135 (7)	−0.0085 (6)	−0.0040 (7)
C7	0.0527 (9)	0.0491 (9)	0.0562 (10)	−0.0207 (7)	−0.0100 (7)	0.0083 (7)
C7'	0.0453 (8)	0.0435 (8)	0.0574 (9)	−0.0176 (7)	−0.0105 (7)	−0.0017 (7)
C8'	0.0432 (8)	0.0393 (7)	0.0479 (8)	−0.0146 (6)	−0.0084 (6)	0.0016 (6)
C8	0.0489 (8)	0.0442 (8)	0.0464 (8)	−0.0151 (7)	−0.0093 (7)	0.0042 (7)
C9'	0.0413 (8)	0.0439 (8)	0.0480 (8)	−0.0145 (6)	−0.0082 (6)	0.0016 (6)
C9	0.0495 (9)	0.0514 (9)	0.0483 (9)	−0.0169 (7)	−0.0092 (7)	0.0025 (7)
C10'	0.0366 (7)	0.0411 (7)	0.0469 (8)	−0.0125 (6)	−0.0054 (6)	0.0020 (6)
C10	0.0469 (8)	0.0469 (8)	0.0472 (9)	−0.0137 (7)	−0.0110 (7)	−0.0008 (7)
C11	0.0499 (9)	0.0575 (10)	0.0520 (9)	−0.0134 (8)	−0.0085 (7)	−0.0041 (8)
C11'	0.0521 (9)	0.0501 (9)	0.0459 (9)	−0.0169 (7)	−0.0061 (7)	0.0022 (7)
C12'	0.0617 (10)	0.0544 (10)	0.0585 (10)	−0.0194 (8)	−0.0012 (8)	−0.0122 (8)
C12	0.0565 (10)	0.0572 (11)	0.0749 (13)	−0.0128 (9)	−0.0129 (9)	−0.0175 (9)
C13	0.0742 (13)	0.0469 (10)	0.0918 (16)	−0.0160 (9)	−0.0213 (11)	0.0011 (10)
C13'	0.0523 (10)	0.0404 (8)	0.0825 (13)	−0.0135 (7)	−0.0015 (9)	0.0004 (9)
C14'	0.0475 (9)	0.0502 (9)	0.0667 (11)	−0.0122 (7)	−0.0084 (8)	0.0154 (8)
C14	0.0906 (15)	0.0569 (11)	0.0682 (12)	−0.0203 (10)	−0.0163 (11)	0.0143 (10)
C15	0.0727 (12)	0.0522 (10)	0.0505 (10)	−0.0154 (9)	−0.0103 (9)	0.0018 (8)
C15'	0.0441 (8)	0.0505 (9)	0.0480 (9)	−0.0125 (7)	−0.0075 (7)	0.0042 (7)
C16	0.0454 (8)	0.0494 (8)	0.0485 (9)	−0.0218 (7)	−0.0079 (7)	−0.0002 (7)
C16'	0.0414 (7)	0.0425 (8)	0.0492 (8)	−0.0202 (6)	−0.0090 (6)	0.0036 (6)
C17'	0.0431 (8)	0.0557 (9)	0.0591 (10)	−0.0130 (7)	−0.0135 (7)	−0.0017 (8)
C17	0.0479 (9)	0.0646 (11)	0.0661 (11)	−0.0161 (8)	−0.0030 (8)	0.0049 (9)
C18'	0.0569 (10)	0.0734 (12)	0.0590 (11)	−0.0206 (9)	−0.0234 (8)	0.0028 (9)
C18	0.0672 (12)	0.0823 (14)	0.0642 (12)	−0.0260 (11)	0.0116 (10)	−0.0008 (11)
C19	0.0952 (16)	0.0792 (14)	0.0492 (10)	−0.0406 (12)	−0.0055 (10)	0.0034 (10)
C19'	0.0677 (11)	0.0671 (11)	0.0502 (10)	−0.0294 (9)	−0.0108 (8)	−0.0017 (8)
C20	0.0764 (13)	0.0684 (12)	0.0638 (12)	−0.0252 (10)	−0.0255 (10)	0.0125 (10)
C20'	0.0509 (9)	0.0571 (10)	0.0606 (11)	−0.0166 (8)	0.0010 (8)	−0.0061 (8)
C21'	0.0417 (8)	0.0506 (9)	0.0590 (10)	−0.0143 (7)	−0.0116 (7)	0.0040 (7)
C21	0.0479 (9)	0.0632 (10)	0.0577 (10)	−0.0182 (8)	−0.0090 (8)	0.0008 (8)
N1	0.0466 (7)	0.0470 (7)	0.0483 (7)	−0.0194 (6)	−0.0016 (6)	−0.0014 (6)
N1'	0.0433 (7)	0.0406 (6)	0.0490 (7)	−0.0177 (5)	−0.0130 (5)	0.0048 (5)
O1'	0.0880 (9)	0.0694 (8)	0.0565 (7)	−0.0497 (7)	−0.0219 (7)	0.0190 (6)
O1	0.0812 (9)	0.0753 (9)	0.0569 (7)	−0.0428 (7)	−0.0059 (6)	−0.0125 (6)
O2'	0.0451 (6)	0.0798 (9)	0.0639 (8)	−0.0232 (6)	0.0018 (6)	−0.0145 (7)
O2	0.0564 (7)	0.0859 (9)	0.0659 (8)	−0.0249 (7)	−0.0245 (6)	0.0188 (7)
O3	0.0687 (8)	0.0578 (7)	0.0618 (8)	−0.0197 (6)	0.0071 (6)	0.0036 (6)
O3'	0.0687 (8)	0.0488 (7)	0.0688 (8)	−0.0171 (6)	−0.0303 (6)	−0.0006 (6)
S1'	0.0479 (2)	0.0545 (2)	0.0467 (2)	−0.02702 (18)	−0.00772 (17)	0.00296 (17)
S1	0.0513 (2)	0.0616 (3)	0.0474 (2)	−0.0268 (2)	−0.01145 (18)	0.00232 (19)

C1—C2	1.391 (2)	C12'—C13'	1.373 (3)
C1—C6	1.406 (2)	C12'—H12'	0.9300
C1—N1	1.414 (2)	C12—C13	1.379 (3)
C1'—C6'	1.397 (2)	C12—H12	0.9300
C1'—C2'	1.397 (2)	C13—C14	1.377 (3)
C1'—N1'	1.4150 (18)	C13—H13	0.9300
C2'—C3'	1.378 (3)	C13'—C14'	1.386 (3)
C2'—H2'	0.9300	C13'—H13'	0.9300
C2—C3	1.378 (3)	C14'—C15'	1.372 (2)
C2—H2	0.9300	C14'—H14'	0.9300
C3—C4	1.383 (3)	C14—C15	1.387 (3)
C3—H3	0.9300	C14—H14	0.9300
C3'—C4'	1.393 (3)	C15—H15	0.9300
C3'—H3'	0.9300	C15'—H15'	0.9300
C4'—C5'	1.370 (3)	C16—C17	1.374 (2)
C4'—H4'	0.9300	C16—C21	1.381 (2)
C4—C5	1.372 (3)	C16—S1	1.7551 (16)
C4—H4	0.9300	C16'—C17'	1.384 (2)
C5—C6	1.398 (2)	C16'—C21'	1.384 (2)
C5—H5	0.9300	C16'—S1'	1.7563 (16)
C5'—C6'	1.404 (2)	C17'—C18'	1.383 (3)
C5'—H5'	0.9300	C17'—H17'	0.9300
C6—C7	1.425 (2)	C17—C18	1.385 (3)
C6'—C7'	1.423 (2)	C17—H17	0.9300
C7—C8	1.350 (2)	C18'—C19'	1.375 (3)
C7—H7	0.9300	C18'—H18'	0.9300
C7'—C8'	1.352 (2)	C18—C19	1.374 (3)
C7'—H7'	0.9300	C18—H18	0.9300
C8'—N1'	1.4179 (18)	C19—C20	1.376 (3)
C8'—C9'	1.477 (2)	C19—H19	0.9300
C8—N1	1.416 (2)	C19'—C20'	1.380 (3)
C8—C9	1.479 (2)	C19'—H19'	0.9300
C9'—O3'	1.2158 (19)	C20—C21	1.376 (3)
C9'—C10'	1.486 (2)	C20—H20	0.9300
C9—O3	1.216 (2)	C20'—C21'	1.379 (3)
C9—C10	1.487 (2)	C20'—H20'	0.9300
C10'—C11'	1.389 (2)	C21'—H21'	0.9300
C10'—C15'	1.390 (2)	C21—H21	0.9300
C10—C11	1.388 (2)	N1—S1	1.6734 (13)
C10—C15	1.393 (2)	N1'—S1'	1.6761 (12)
C11—C12	1.375 (2)	O1'—S1'	1.4254 (12)
C11—H11	0.9300	O1—S1	1.4264 (14)
C11'—C12'	1.388 (2)	O2'—S1'	1.4197 (13)
C11'—H11'	0.9300	O2—S1	1.4217 (13)
C2—C1—C6	121.55 (16)	C14—C13—C12	120.26 (18)
C2—C1—N1	131.80 (16)	C14—C13—H13	119.9
C6—C1—N1	106.64 (14)	C12—C13—H13	119.9
C6'—C1'—C2'	121.26 (14)	C12'—C13'—C14'	120.30 (16)
C6'—C1'—N1'	107.10 (13)	C12'—C13'—H13'	119.8
C2'—C1'—N1'	131.59 (14)	C14'—C13'—H13'	119.8
C3'—C2'—C1'	117.05 (17)	C15'—C14'—C13'	119.78 (16)
C3'—C2'—H2'	121.5	C15'—C14'—H14'	120.1
C1'—C2'—H2'	121.5	C13'—C14'—H14'	120.1
C3—C2—C1	117.18 (19)	C13—C14—C15	120.16 (19)
C3—C2—H2	121.4	C13—C14—H14	119.9
C1—C2—H2	121.4	C15—C14—H14	119.9
C2—C3—C4	122.13 (19)	C14—C15—C10	119.49 (18)
C2—C3—H3	118.9	C14—C15—H15	120.3
C4—C3—H3	118.9	C10—C15—H15	120.3
C2'—C3'—C4'	122.34 (17)	C14'—C15'—C10'	120.45 (16)
C2'—C3'—H3'	118.8	C14'—C15'—H15'	119.8
C4'—C3'—H3'	118.8	C10'—C15'—H15'	119.8
C5'—C4'—C3'	120.69 (16)	C17—C16—C21	121.50 (16)
C5'—C4'—H4'	119.7	C17—C16—S1	119.44 (13)
C3'—C4'—H4'	119.7	C21—C16—S1	118.96 (13)
C5—C4—C3	120.89 (18)	C17'—C16'—C21'	121.27 (15)
C5—C4—H4	119.6	C17'—C16'—S1'	119.65 (13)
C3—C4—H4	119.6	C21'—C16'—S1'	118.99 (12)
C4—C5—C6	118.82 (18)	C18'—C17'—C16'	118.61 (16)
C4—C5—H5	120.6	C18'—C17'—H17'	120.7
C6—C5—H5	120.6	C16'—C17'—H17'	120.7
C4'—C5'—C6'	118.42 (17)	C16—C17—C18	118.52 (18)
C4'—C5'—H5'	120.8	C16—C17—H17	120.7
C6'—C5'—H5'	120.8	C18—C17—H17	120.7
C5—C6—C1	119.41 (16)	C19'—C18'—C17'	120.57 (17)
C5—C6—C7	132.82 (17)	C19'—C18'—H18'	119.7
C1—C6—C7	107.72 (14)	C17'—C18'—H18'	119.7
C1'—C6'—C5'	120.22 (15)	C19—C18—C17	120.33 (19)
C1'—C6'—C7'	107.86 (13)	C19—C18—H18	119.8
C5'—C6'—C7'	131.83 (16)	C17—C18—H18	119.8
C8—C7—C6	108.95 (15)	C18—C19—C20	120.59 (18)
C8—C7—H7	125.5	C18—C19—H19	119.7
C6—C7—H7	125.5	C20—C19—H19	119.7
C8'—C7'—C6'	108.73 (14)	C18'—C19'—C20'	120.29 (17)
C8'—C7'—H7'	125.6	C18'—C19'—H19'	119.9
C6'—C7'—H7'	125.6	C20'—C19'—H19'	119.9
C7'—C8'—N1'	108.63 (13)	C21—C20—C19	119.68 (18)
C7'—C8'—C9'	126.66 (14)	C21—C20—H20	120.2
N1'—C8'—C9'	123.14 (13)	C19—C20—H20	120.2
C7—C8—N1	108.47 (14)	C21'—C20'—C19'	120.09 (17)
C7—C8—C9	126.76 (15)	C21'—C20'—H20'	120.0
N1—C8—C9	123.09 (14)	C19'—C20'—H20'	120.0
O3'—C9'—C8'	120.50 (14)	C20'—C21'—C16'	119.15 (15)
O3'—C9'—C10'	121.06 (14)	C20'—C21'—H21'	120.4
C8'—C9'—C10'	118.33 (13)	C16'—C21'—H21'	120.4
O3—C9—C8	120.57 (15)	C20—C21—C16	119.37 (17)
O3—C9—C10	121.10 (15)	C20—C21—H21	120.3
C8—C9—C10	118.26 (14)	C16—C21—H21	120.3
C11'—C10'—C15'	119.57 (14)	C1—N1—C8	108.21 (13)
C11'—C10'—C9'	122.77 (14)	C1—N1—S1	126.37 (11)
C15'—C10'—C9'	117.61 (14)	C8—N1—S1	124.59 (11)
C11—C10—C15	119.75 (16)	C1'—N1'—C8'	107.66 (12)
C11—C10—C9	118.40 (15)	C1'—N1'—S1'	126.32 (10)
C15—C10—C9	121.76 (15)	C8'—N1'—S1'	124.95 (10)
C12—C11—C10	120.12 (17)	O2'—S1'—O1'	119.73 (8)
C12—C11—H11	119.9	O2'—S1'—N1'	107.50 (7)
C10—C11—H11	119.9	O1'—S1'—N1'	104.83 (7)
C12'—C11'—C10'	119.56 (16)	O2'—S1'—C16'	110.44 (8)
C12'—C11'—H11'	120.2	O1'—S1'—C16'	107.87 (8)
C10'—C11'—H11'	120.2	N1'—S1'—C16'	105.46 (7)
C13'—C12'—C11'	120.25 (18)	O2—S1—O1	119.56 (9)
C13'—C12'—H12'	119.9	O2—S1—N1	107.30 (7)
C11'—C12'—H12'	119.9	O1—S1—N1	105.18 (7)
C11—C12—C13	120.17 (18)	O2—S1—C16	110.09 (8)
C11—C12—H12	119.9	O1—S1—C16	108.48 (8)
C13—C12—H12	119.9	N1—S1—C16	105.20 (7)
C6'—C1'—C2'—C3'	−1.4 (2)	C13'—C14'—C15'—C10'	−3.2 (2)
N1'—C1'—C2'—C3'	175.84 (16)	C11'—C10'—C15'—C14'	2.0 (2)
C6—C1—C2—C3	1.7 (3)	C9'—C10'—C15'—C14'	179.39 (14)
N1—C1—C2—C3	−176.50 (17)	C21'—C16'—C17'—C18'	−0.8 (2)
C1—C2—C3—C4	−0.6 (3)	S1'—C16'—C17'—C18'	−177.48 (14)
C1'—C2'—C3'—C4'	0.1 (3)	C21—C16—C17—C18	0.8 (3)
C2'—C3'—C4'—C5'	0.6 (3)	S1—C16—C17—C18	177.02 (16)
C2—C3—C4—C5	−0.5 (3)	C16'—C17'—C18'—C19'	0.2 (3)
C3—C4—C5—C6	0.4 (3)	C16—C17—C18—C19	−0.1 (3)
C3'—C4'—C5'—C6'	0.1 (3)	C17—C18—C19—C20	−0.6 (3)
C4—C5—C6—C1	0.7 (3)	C17'—C18'—C19'—C20'	0.5 (3)
C4—C5—C6—C7	177.74 (18)	C18—C19—C20—C21	0.5 (3)
C2—C1—C6—C5	−1.8 (2)	C18'—C19'—C20'—C21'	−0.5 (3)
N1—C1—C6—C5	176.81 (15)	C19'—C20'—C21'—C16'	−0.2 (3)
C2—C1—C6—C7	−179.50 (16)	C17'—C16'—C21'—C20'	0.8 (2)
N1—C1—C6—C7	−0.91 (17)	S1'—C16'—C21'—C20'	177.51 (13)
C2'—C1'—C6'—C5'	2.1 (2)	C19—C20—C21—C16	0.2 (3)
N1'—C1'—C6'—C5'	−175.76 (14)	C17—C16—C21—C20	−0.9 (3)
C2'—C1'—C6'—C7'	179.13 (15)	S1—C16—C21—C20	−177.14 (14)
N1'—C1'—C6'—C7'	1.29 (17)	C2—C1—N1—C8	178.72 (17)
C4'—C5'—C6'—C1'	−1.4 (2)	C6—C1—N1—C8	0.33 (17)
C4'—C5'—C6'—C7'	−177.59 (17)	C2—C1—N1—S1	−11.4 (3)
C5—C6—C7—C8	−176.10 (18)	C6—C1—N1—S1	170.23 (11)
C1—C6—C7—C8	1.19 (19)	C7—C8—N1—C1	0.41 (18)
C1'—C6'—C7'—C8'	−1.27 (18)	C9—C8—N1—C1	−165.74 (14)
C5'—C6'—C7'—C8'	175.31 (17)	C7—C8—N1—S1	−169.71 (12)
C6'—C7'—C8'—N1'	0.73 (18)	C9—C8—N1—S1	24.1 (2)
C6'—C7'—C8'—C9'	−165.23 (15)	C6'—C1'—N1'—C8'	−0.86 (16)
C6—C7—C8—N1	−0.98 (18)	C2'—C1'—N1'—C8'	−178.39 (16)
C6—C7—C8—C9	164.52 (15)	C6'—C1'—N1'—S1'	−169.40 (11)
C7'—C8'—C9'—O3'	139.58 (18)	C2'—C1'—N1'—S1'	13.1 (2)
N1'—C8'—C9'—O3'	−24.5 (2)	C7'—C8'—N1'—C1'	0.08 (17)
C7'—C8'—C9'—C10'	−36.7 (2)	C9'—C8'—N1'—C1'	166.64 (14)
N1'—C8'—C9'—C10'	159.25 (14)	C7'—C8'—N1'—S1'	168.82 (12)
C7—C8—C9—O3	−135.37 (19)	C9'—C8'—N1'—S1'	−24.6 (2)
N1—C8—C9—O3	28.2 (2)	C1'—N1'—S1'—O2'	137.76 (13)
C7—C8—C9—C10	41.5 (2)	C8'—N1'—S1'—O2'	−28.89 (15)
N1—C8—C9—C10	−154.98 (15)	C1'—N1'—S1'—O1'	9.35 (15)
O3'—C9'—C10'—C11'	149.60 (16)	C8'—N1'—S1'—O1'	−157.30 (13)
C8'—C9'—C10'—C11'	−34.2 (2)	C1'—N1'—S1'—C16'	−104.39 (13)
O3'—C9'—C10'—C15'	−27.7 (2)	C8'—N1'—S1'—C16'	88.95 (14)
C8'—C9'—C10'—C15'	148.56 (14)	C17'—C16'—S1'—O2'	−8.10 (15)
O3—C9—C10—C11	27.8 (2)	C21'—C16'—S1'—O2'	175.18 (12)
C8—C9—C10—C11	−148.99 (15)	C17'—C16'—S1'—O1'	124.45 (13)
O3—C9—C10—C15	−148.71 (18)	C21'—C16'—S1'—O1'	−52.28 (14)
C8—C9—C10—C15	34.5 (2)	C17'—C16'—S1'—N1'	−123.95 (13)
C15—C10—C11—C12	−1.1 (3)	C21'—C16'—S1'—N1'	59.33 (13)
C9—C10—C11—C12	−177.72 (16)	C1—N1—S1—O2	−140.16 (13)
C15'—C10'—C11'—C12'	0.8 (2)	C8—N1—S1—O2	28.17 (15)
C9'—C10'—C11'—C12'	−176.44 (15)	C1—N1—S1—O1	−11.85 (15)
C10'—C11'—C12'—C13'	−2.4 (3)	C8—N1—S1—O1	156.48 (13)
C10—C11—C12—C13	2.1 (3)	C1—N1—S1—C16	102.62 (14)
C11—C12—C13—C14	−1.4 (3)	C8—N1—S1—C16	−89.06 (14)
C11'—C12'—C13'—C14'	1.2 (3)	C17—C16—S1—O2	13.85 (17)
C12'—C13'—C14'—C15'	1.6 (3)	C21—C16—S1—O2	−169.87 (14)
C12—C13—C14—C15	−0.4 (3)	C17—C16—S1—O1	−118.69 (15)
C13—C14—C15—C10	1.4 (3)	C21—C16—S1—O1	57.58 (15)
C11—C10—C15—C14	−0.6 (3)	C17—C16—S1—N1	129.16 (15)
C9—C10—C15—C14	175.87 (18)	C21—C16—S1—N1	−54.56 (15)