Ethyl 3-[2-(3,4-dimeth-oxy-benz-yl)-1-phenyl-sulfonyl-1H-indol-3-yl]acrylate chloro-form hemisolvate.

In the title compound, C(28)H(27)NO(6)S·0.5CHCl(3), the ethyl acrylate substituent adopts an extented conformation with all torsion angles close to 180°. The chloro-form solvent mol-ecule is disordered across an inversion centre and is therefore half occupied. The mol-ecular packing is controlled by inter-molecular C-H⋯O inter-actions.

Related literature

For general background to indoles, see: Hu et al. (2005 ▶); Nieto et al. (2005 ▶); Mathiesen et al. (2005 ▶); Olgen & Nebioglu (2002 ▶). For the sulfonyl moiety, see: Bassindale (1984 ▶). For hybridization, see: Beddoes et al. (1986 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C28H27NO6S·0.5CHCl3

M = 565.25

Triclinic,

a = 10.2154 (3) Å

b = 12.0504 (4) Å

c = 12.6310 (4) Å

α = 70.602 (2)°

β = 69.613 (1)°

γ = 77.056 (2)°

V = 1364.39 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.31 mm−1

T = 293 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ▶) T min = 0.913, T max = 0.941

38797 measured reflections

10612 independent reflections

7709 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.189

S = 1.04

10612 reflections

364 parameters

27 restraints

H-atom parameters constrained

Δρmax = 0.73 e Å−3

Δρmin = −0.46 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXS97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811017740/bt5508sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811017740/bt5508Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811017740/bt5508Isup3.cml

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

C28H27NO6S·0.5CHCl3	Z = 2
Mr = 565.25	F(000) = 590
Triclinic, P1	Dx = 1.376 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.2154 (3) Å	Cell parameters from 10612 reflections
b = 12.0504 (4) Å	θ = 1.8–34.4°
c = 12.6310 (4) Å	µ = 0.31 mm−1
α = 70.602 (2)°	T = 293 K
β = 69.613 (1)°	Block, yellow
γ = 77.056 (2)°	0.30 × 0.25 × 0.20 mm
V = 1364.39 (7) Å3

Bruker Kappa APEXII area-detector diffractometer	10612 independent reflections
Radiation source: fine-focus sealed tube	7709 reflections with I > 2σ(I)
graphite	Rint = 0.026
ω and φ scans	θmax = 34.4°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −15→16
Tmin = 0.913, Tmax = 0.941	k = −18→18
38797 measured reflections	l = −18→19

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.189	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.1059P)2 + 0.3616P] where P = (Fo2 + 2Fc2)/3
10612 reflections	(Δ/σ)max = 0.005
364 parameters	Δρmax = 0.73 e Å−3
27 restraints	Δρmin = −0.46 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	Occ. (<1)
C2	0.72857 (13)	0.61852 (12)	0.05863 (12)	0.0264 (2)
C3	0.81718 (13)	0.63351 (12)	−0.05351 (12)	0.0274 (2)
C4	0.95289 (13)	0.65050 (12)	−0.05427 (12)	0.0263 (2)
C5	1.07996 (14)	0.66763 (13)	−0.14331 (13)	0.0315 (3)
H5	1.0889	0.6670	−0.2189	0.038*
C6	1.19275 (15)	0.68563 (15)	−0.11662 (15)	0.0364 (3)
H6	1.2784	0.6974	−0.1750	0.044*
C7	1.17913 (15)	0.68629 (15)	−0.00368 (16)	0.0379 (3)
H7	1.2559	0.7000	0.0116	0.045*
C8	1.05530 (15)	0.66722 (15)	0.08678 (14)	0.0356 (3)
H8	1.0476	0.6666	0.1625	0.043*
C9	0.94241 (13)	0.64898 (12)	0.05935 (12)	0.0279 (2)
C10	0.70544 (17)	0.78432 (16)	0.26272 (14)	0.0377 (3)
C11	0.5742 (2)	0.84292 (17)	0.25639 (15)	0.0432 (4)
H11	0.5084	0.8035	0.2523	0.052*
C12	0.5421 (3)	0.9606 (2)	0.2561 (2)	0.0574 (5)
H12	0.4541	1.0006	0.2523	0.069*
C13	0.6404 (3)	1.0186 (2)	0.2616 (3)	0.0744 (8)
H13	0.6187	1.0980	0.2609	0.089*
C14	0.7695 (3)	0.9599 (3)	0.2680 (3)	0.0806 (9)
H14	0.8348	0.9999	0.2720	0.097*
C15	0.8049 (2)	0.8418 (2)	0.2685 (2)	0.0587 (6)
H15	0.8931	0.8022	0.2727	0.070*
C16	0.58220 (13)	0.58587 (12)	0.10469 (13)	0.0292 (3)
H16A	0.5727	0.5253	0.1792	0.035*
H16B	0.5688	0.5514	0.0504	0.035*
C17	0.46644 (13)	0.68702 (12)	0.12265 (12)	0.0269 (2)
C18	0.47327 (14)	0.79830 (13)	0.04363 (13)	0.0312 (3)
H18	0.5530	0.8133	−0.0208	0.037*
C19	0.36222 (16)	0.88845 (13)	0.05909 (14)	0.0347 (3)
H19	0.3682	0.9628	0.0047	0.042*
C20	0.24365 (15)	0.86818 (14)	0.15431 (15)	0.0350 (3)
C21	0.23710 (14)	0.75648 (14)	0.23783 (13)	0.0326 (3)
C22	0.34699 (14)	0.66710 (13)	0.22105 (12)	0.0296 (3)
H22	0.3417	0.5928	0.2756	0.036*
C23	0.1240 (3)	1.0559 (2)	0.0848 (3)	0.0857 (10)
H23A	0.1932	1.1019	0.0787	0.129*
H23B	0.0323	1.1002	0.1029	0.129*
H23C	0.1440	1.0385	0.0115	0.129*
C24	0.1089 (2)	0.6366 (2)	0.42176 (19)	0.0577 (5)
H24A	0.1140	0.5729	0.3903	0.087*
H24B	0.0213	0.6415	0.4826	0.087*
H24C	0.1855	0.6224	0.4539	0.087*
C25	0.79102 (15)	0.63214 (13)	−0.15877 (13)	0.0311 (3)
H25	0.8700	0.6102	−0.2158	0.037*
C26	0.67095 (15)	0.65761 (15)	−0.18607 (13)	0.0342 (3)
H26	0.5864	0.6751	−0.1316	0.041*
C27	0.67332 (16)	0.65776 (16)	−0.30294 (13)	0.0358 (3)
C28	0.5395 (2)	0.6890 (3)	−0.43115 (17)	0.0634 (6)
H28A	0.5753	0.6117	−0.4448	0.076*
H28B	0.5976	0.7465	−0.4927	0.076*
C29	0.3931 (3)	0.7211 (3)	−0.4337 (2)	0.0673 (7)
H29A	0.3356	0.6655	−0.3710	0.101*
H29B	0.3881	0.7196	−0.5077	0.101*
H29C	0.3599	0.7993	−0.4242	0.101*
N1	0.80387 (12)	0.62707 (11)	0.13020 (10)	0.0292 (2)
O1	0.61261 (13)	0.58330 (11)	0.31986 (10)	0.0420 (3)
O2	0.85541 (15)	0.58180 (14)	0.31850 (11)	0.0509 (3)
O3	0.12766 (14)	0.94873 (12)	0.17533 (14)	0.0550 (4)
O4	0.11775 (12)	0.74569 (12)	0.33019 (12)	0.0468 (3)
O7	0.77576 (14)	0.63380 (17)	−0.37800 (13)	0.0608 (4)
O8	0.54527 (12)	0.68657 (14)	−0.31723 (10)	0.0482 (3)
S1	0.74189 (4)	0.63276 (4)	0.26998 (3)	0.03379 (10)
C30	1.0269 (8)	−0.0254 (6)	0.4558 (6)	0.113 (3)	0.50
H30A	1.0428	−0.0660	0.3979	0.136*	0.50
Cl1	0.9317 (6)	0.1115 (4)	0.4302 (5)	0.199 (2)	0.50
Cl2	0.9683 (8)	−0.1068 (4)	0.5950 (4)	0.223 (3)	0.50
Cl3	1.1858 (5)	0.0222 (6)	0.4566 (6)	0.241 (2)	0.50

	U11	U22	U33	U12	U13	U23
C2	0.0239 (5)	0.0266 (6)	0.0284 (6)	−0.0029 (4)	−0.0068 (4)	−0.0083 (5)
C3	0.0237 (5)	0.0287 (6)	0.0294 (6)	−0.0024 (4)	−0.0067 (4)	−0.0093 (5)
C4	0.0233 (5)	0.0246 (6)	0.0297 (6)	−0.0015 (4)	−0.0063 (4)	−0.0084 (5)
C5	0.0256 (6)	0.0342 (7)	0.0311 (6)	−0.0035 (5)	−0.0032 (5)	−0.0102 (5)
C6	0.0237 (6)	0.0394 (8)	0.0433 (8)	−0.0042 (5)	−0.0032 (5)	−0.0149 (6)
C7	0.0250 (6)	0.0452 (8)	0.0483 (9)	−0.0049 (5)	−0.0097 (6)	−0.0199 (7)
C8	0.0286 (6)	0.0450 (8)	0.0383 (8)	−0.0033 (5)	−0.0102 (5)	−0.0186 (6)
C9	0.0242 (5)	0.0283 (6)	0.0311 (6)	−0.0017 (4)	−0.0072 (4)	−0.0102 (5)
C10	0.0395 (7)	0.0459 (8)	0.0285 (7)	−0.0127 (6)	−0.0010 (5)	−0.0162 (6)
C11	0.0526 (9)	0.0454 (9)	0.0356 (8)	−0.0058 (7)	−0.0139 (7)	−0.0158 (7)
C12	0.0707 (13)	0.0472 (11)	0.0538 (12)	−0.0002 (9)	−0.0168 (10)	−0.0197 (9)
C13	0.0876 (18)	0.0528 (13)	0.0797 (18)	−0.0212 (12)	0.0009 (14)	−0.0335 (12)
C14	0.0689 (15)	0.0828 (18)	0.102 (2)	−0.0386 (14)	0.0080 (14)	−0.0570 (17)
C15	0.0406 (9)	0.0773 (15)	0.0694 (14)	−0.0203 (9)	0.0008 (8)	−0.0441 (12)
C16	0.0246 (5)	0.0294 (6)	0.0327 (6)	−0.0057 (4)	−0.0051 (5)	−0.0095 (5)
C17	0.0223 (5)	0.0303 (6)	0.0278 (6)	−0.0055 (4)	−0.0055 (4)	−0.0081 (5)
C18	0.0268 (6)	0.0339 (7)	0.0293 (6)	−0.0069 (5)	−0.0041 (5)	−0.0066 (5)
C19	0.0325 (6)	0.0293 (7)	0.0364 (7)	−0.0056 (5)	−0.0072 (5)	−0.0038 (5)
C20	0.0287 (6)	0.0310 (7)	0.0409 (8)	−0.0015 (5)	−0.0059 (5)	−0.0104 (6)
C21	0.0250 (6)	0.0362 (7)	0.0332 (7)	−0.0061 (5)	−0.0021 (5)	−0.0104 (6)
C22	0.0260 (5)	0.0300 (6)	0.0296 (6)	−0.0064 (4)	−0.0052 (5)	−0.0055 (5)
C23	0.0520 (12)	0.0391 (11)	0.113 (2)	0.0090 (9)	0.0024 (13)	0.0079 (12)
C24	0.0444 (9)	0.0549 (11)	0.0452 (10)	−0.0098 (8)	0.0117 (8)	−0.0017 (8)
C25	0.0298 (6)	0.0364 (7)	0.0278 (6)	−0.0047 (5)	−0.0068 (5)	−0.0110 (5)
C26	0.0302 (6)	0.0446 (8)	0.0295 (6)	−0.0017 (5)	−0.0078 (5)	−0.0156 (6)
C27	0.0322 (6)	0.0477 (8)	0.0293 (7)	−0.0073 (6)	−0.0066 (5)	−0.0141 (6)
C28	0.0493 (10)	0.116 (2)	0.0294 (8)	−0.0157 (11)	−0.0110 (7)	−0.0228 (10)
C29	0.0630 (13)	0.103 (2)	0.0438 (11)	−0.0165 (13)	−0.0262 (10)	−0.0151 (12)
N1	0.0253 (5)	0.0349 (6)	0.0271 (5)	−0.0041 (4)	−0.0054 (4)	−0.0106 (4)
O1	0.0429 (6)	0.0477 (7)	0.0297 (5)	−0.0165 (5)	−0.0017 (4)	−0.0060 (5)
O2	0.0485 (7)	0.0687 (9)	0.0352 (6)	−0.0030 (6)	−0.0203 (5)	−0.0084 (6)
O3	0.0369 (6)	0.0367 (6)	0.0681 (9)	0.0056 (5)	0.0009 (6)	−0.0092 (6)
O4	0.0319 (5)	0.0444 (7)	0.0440 (7)	−0.0035 (5)	0.0078 (5)	−0.0077 (5)
O7	0.0395 (7)	0.1053 (13)	0.0413 (7)	−0.0004 (7)	−0.0046 (5)	−0.0383 (8)
O8	0.0346 (6)	0.0831 (10)	0.0283 (5)	−0.0080 (6)	−0.0089 (4)	−0.0174 (6)
S1	0.03402 (18)	0.0409 (2)	0.02481 (17)	−0.00679 (14)	−0.00670 (12)	−0.00787 (14)
C30	0.145 (6)	0.099 (5)	0.098 (5)	0.038 (4)	−0.053 (4)	−0.047 (4)
Cl1	0.273 (5)	0.147 (3)	0.235 (5)	0.091 (3)	−0.201 (5)	−0.071 (3)
Cl2	0.327 (6)	0.129 (3)	0.147 (3)	−0.070 (4)	0.001 (4)	−0.003 (2)
Cl3	0.162 (3)	0.292 (6)	0.246 (5)	0.010 (4)	−0.066 (3)	−0.065 (4)

C2—C3	1.3669 (19)	C23—O3	1.416 (3)
C2—N1	1.4146 (17)	C23—H23A	0.9600
C2—C16	1.4948 (17)	C23—H23B	0.9600
C3—C4	1.4424 (17)	C23—H23C	0.9600
C3—C25	1.4503 (19)	C24—O4	1.430 (2)
C4—C5	1.3932 (18)	C24—H24A	0.9600
C4—C9	1.3956 (19)	C24—H24B	0.9600
C5—C6	1.385 (2)	C24—H24C	0.9600
C5—H5	0.9300	C25—C26	1.332 (2)
C6—C7	1.387 (2)	C25—H25	0.9300
C6—H6	0.9300	C26—C27	1.467 (2)
C7—C8	1.381 (2)	C26—H26	0.9300
C7—H7	0.9300	C27—O7	1.1969 (19)
C8—C9	1.3931 (19)	C27—O8	1.3355 (19)
C8—H8	0.9300	C28—O8	1.451 (2)
C9—N1	1.4148 (17)	C28—C29	1.467 (3)
C10—C11	1.384 (3)	C28—H28A	0.9700
C10—C15	1.385 (2)	C28—H28B	0.9700
C10—S1	1.7581 (18)	C29—H29A	0.9600
C11—C12	1.381 (3)	C29—H29B	0.9600
C11—H11	0.9300	C29—H29C	0.9600
C12—C13	1.377 (4)	N1—S1	1.6749 (12)
C12—H12	0.9300	O1—S1	1.4211 (12)
C13—C14	1.366 (4)	O2—S1	1.4225 (13)
C13—H13	0.9300	C30—C30i	1.341 (14)
C14—C15	1.387 (4)	C30—Cl2i	1.512 (8)
C14—H14	0.9300	C30—Cl1i	1.601 (8)
C15—H15	0.9300	C30—Cl2	1.673 (7)
C16—C17	1.5121 (19)	C30—Cl1	1.708 (6)
C16—H16A	0.9700	C30—Cl3	1.842 (8)
C16—H16B	0.9700	C30—Cl3i	2.065 (10)
C17—C18	1.380 (2)	C30—H30A	0.9600
C17—C22	1.4028 (18)	Cl1—Cl2i	0.952 (7)
C18—C19	1.393 (2)	Cl1—C30i	1.601 (8)
C18—H18	0.9300	Cl1—Cl3i	2.054 (8)
C19—C20	1.377 (2)	Cl2—Cl1i	0.952 (7)
C19—H19	0.9300	Cl2—C30i	1.512 (8)
C20—O3	1.3613 (19)	Cl2—Cl3i	1.871 (8)
C20—C21	1.406 (2)	Cl3—Cl2i	1.871 (8)
C21—O4	1.3577 (17)	Cl3—Cl1i	2.054 (8)
C21—C22	1.382 (2)	Cl3—C30i	2.065 (10)
C22—H22	0.9300
C3—C2—N1	108.14 (11)	C26—C25—H25	115.1
C3—C2—C16	127.64 (12)	C3—C25—H25	115.1
N1—C2—C16	123.93 (12)	C25—C26—C27	119.37 (13)
C2—C3—C4	108.30 (12)	C25—C26—H26	120.3
C2—C3—C25	129.64 (12)	C27—C26—H26	120.3
C4—C3—C25	122.05 (12)	O7—C27—O8	122.46 (15)
C5—C4—C9	119.96 (12)	O7—C27—C26	125.42 (15)
C5—C4—C3	132.26 (13)	O8—C27—C26	112.11 (13)
C9—C4—C3	107.78 (11)	O8—C28—C29	109.08 (17)
C6—C5—C4	118.49 (14)	O8—C28—H28A	109.9
C6—C5—H5	120.8	C29—C28—H28A	109.9
C4—C5—H5	120.8	O8—C28—H28B	109.9
C5—C6—C7	120.58 (13)	C29—C28—H28B	109.9
C5—C6—H6	119.7	H28A—C28—H28B	108.3
C7—C6—H6	119.7	C28—C29—H29A	109.5
C8—C7—C6	122.15 (14)	C28—C29—H29B	109.5
C8—C7—H7	118.9	H29A—C29—H29B	109.5
C6—C7—H7	118.9	C28—C29—H29C	109.5
C7—C8—C9	116.95 (14)	H29A—C29—H29C	109.5
C7—C8—H8	121.5	H29B—C29—H29C	109.5
C9—C8—H8	121.5	C2—N1—C9	108.64 (11)
C8—C9—C4	121.85 (13)	C2—N1—S1	128.29 (9)
C8—C9—N1	131.06 (13)	C9—N1—S1	122.44 (10)
C4—C9—N1	107.10 (11)	C20—O3—C23	116.43 (16)
C11—C10—C15	121.11 (18)	C21—O4—C24	117.78 (14)
C11—C10—S1	118.80 (13)	C27—O8—C28	115.21 (14)
C15—C10—S1	120.02 (16)	O1—S1—O2	120.63 (8)
C12—C11—C10	119.32 (19)	O1—S1—N1	106.73 (7)
C12—C11—H11	120.3	O2—S1—N1	105.65 (7)
C10—C11—H11	120.3	O1—S1—C10	108.29 (8)
C13—C12—C11	120.1 (2)	O2—S1—C10	108.90 (9)
C13—C12—H12	120.0	N1—S1—C10	105.65 (7)
C11—C12—H12	120.0	C30i—C30—Cl2i	71.5 (6)
C14—C13—C12	120.2 (2)	C30i—C30—Cl1i	70.3 (6)
C14—C13—H13	119.9	Cl2i—C30—Cl1i	128.4 (6)
C12—C13—H13	119.9	C30i—C30—Cl2	59.0 (5)
C13—C14—C15	121.2 (2)	Cl2i—C30—Cl2	130.5 (5)
C13—C14—H14	119.4	Cl1i—C30—Cl2	33.7 (3)
C15—C14—H14	119.4	C30i—C30—Cl1	62.0 (5)
C10—C15—C14	118.2 (2)	Cl2i—C30—Cl1	33.7 (3)
C10—C15—H15	120.9	Cl1i—C30—Cl1	132.3 (4)
C14—C15—H15	120.9	Cl2—C30—Cl1	112.0 (4)
C2—C16—C17	115.26 (11)	C30i—C30—Cl3	79.2 (7)
C2—C16—H16A	108.5	Cl2i—C30—Cl3	67.0 (4)
C17—C16—H16A	108.5	Cl1i—C30—Cl3	72.9 (4)
C2—C16—H16B	108.5	Cl2—C30—Cl3	101.7 (5)
C17—C16—H16B	108.5	Cl1—C30—Cl3	97.4 (4)
H16A—C16—H16B	107.5	C30i—C30—Cl3i	61.2 (6)
C18—C17—C22	118.73 (13)	Cl2i—C30—Cl3i	98.2 (4)
C18—C17—C16	121.92 (12)	Cl1i—C30—Cl3i	92.5 (4)
C22—C17—C16	119.34 (12)	Cl2—C30—Cl3i	59.0 (4)
C17—C18—C19	120.84 (13)	Cl1—C30—Cl3i	65.2 (3)
C17—C18—H18	119.6	Cl3—C30—Cl3i	140.4 (4)
C19—C18—H18	119.6	C30i—C30—H30A	166.2
C20—C19—C18	120.44 (14)	Cl2i—C30—H30A	113.6
C20—C19—H19	119.8	Cl1i—C30—H30A	111.7
C18—C19—H19	119.8	Cl2—C30—H30A	114.6
O3—C20—C19	125.06 (15)	Cl1—C30—H30A	114.5
O3—C20—C21	115.52 (13)	Cl3—C30—H30A	114.6
C19—C20—C21	119.42 (13)	Cl3i—C30—H30A	105.0
O4—C21—C22	125.01 (14)	Cl2i—Cl1—C30i	77.3 (4)
O4—C21—C20	115.26 (13)	Cl2i—Cl1—C30	61.8 (5)
C22—C21—C20	119.73 (13)	C30i—Cl1—C30	47.7 (4)
C21—C22—C17	120.79 (13)	Cl2i—Cl1—Cl3i	126.3 (5)
C21—C22—H22	119.6	C30i—Cl1—Cl3i	59.0 (4)
C17—C22—H22	119.6	C30—Cl1—Cl3i	65.8 (3)
O3—C23—H23A	109.5	Cl1i—Cl2—C30i	84.5 (6)
O3—C23—H23B	109.5	Cl1i—Cl2—C30	69.0 (5)
H23A—C23—H23B	109.5	C30i—Cl2—C30	49.5 (5)
O3—C23—H23C	109.5	Cl1i—Cl2—Cl3i	139.6 (5)
H23A—C23—H23C	109.5	C30i—Cl2—Cl3i	65.0 (4)
H23B—C23—H23C	109.5	C30—Cl2—Cl3i	71.0 (4)
O4—C24—H24A	109.5	C30—Cl3—Cl2i	48.0 (3)
O4—C24—H24B	109.5	C30—Cl3—Cl1i	48.2 (3)
H24A—C24—H24B	109.5	Cl2i—Cl3—Cl1i	91.0 (3)
O4—C24—H24C	109.5	C30—Cl3—C30i	39.6 (4)
H24A—C24—H24C	109.5	Cl2i—Cl3—C30i	50.0 (2)
H24B—C24—H24C	109.5	Cl1i—Cl3—C30i	49.0 (2)
C26—C25—C3	129.71 (14)
N1—C2—C3—C4	0.77 (15)	O7—C27—O8—C28	−1.2 (3)
C16—C2—C3—C4	−173.17 (13)	C26—C27—O8—C28	179.76 (18)
N1—C2—C3—C25	179.76 (14)	C29—C28—O8—C27	179.7 (2)
C16—C2—C3—C25	5.8 (2)	C2—N1—S1—O1	21.70 (15)
C2—C3—C4—C5	178.86 (15)	C9—N1—S1—O1	−168.44 (11)
C25—C3—C4—C5	−0.2 (2)	C2—N1—S1—O2	151.24 (13)
C2—C3—C4—C9	−1.78 (15)	C9—N1—S1—O2	−38.90 (14)
C25—C3—C4—C9	179.13 (13)	C2—N1—S1—C10	−93.43 (13)
C9—C4—C5—C6	−1.5 (2)	C9—N1—S1—C10	76.43 (13)
C3—C4—C5—C6	177.80 (15)	C11—C10—S1—O1	−25.83 (15)
C4—C5—C6—C7	0.1 (2)	C15—C10—S1—O1	151.37 (15)
C5—C6—C7—C8	1.2 (3)	C11—C10—S1—O2	−158.70 (13)
C6—C7—C8—C9	−1.0 (2)	C15—C10—S1—O2	18.50 (18)
C7—C8—C9—C4	−0.4 (2)	C11—C10—S1—N1	88.22 (14)
C7—C8—C9—N1	179.80 (15)	C15—C10—S1—N1	−94.58 (16)
C5—C4—C9—C8	1.7 (2)	C30i—C30—Cl1—Cl2i	98.6 (8)
C3—C4—C9—C8	−177.79 (13)	Cl1i—C30—Cl1—Cl2i	98.6 (8)
C5—C4—C9—N1	−178.49 (12)	Cl2—C30—Cl1—Cl2i	131.0 (6)
C3—C4—C9—N1	2.06 (15)	Cl3—C30—Cl1—Cl2i	25.1 (6)
C15—C10—C11—C12	−0.1 (3)	Cl3i—C30—Cl1—Cl2i	167.8 (7)
S1—C10—C11—C12	177.03 (15)	Cl2i—C30—Cl1—C30i	−98.6 (8)
C10—C11—C12—C13	0.3 (3)	Cl1i—C30—Cl1—C30i	0.0
C11—C12—C13—C14	−0.4 (4)	Cl2—C30—Cl1—C30i	32.3 (5)
C12—C13—C14—C15	0.3 (5)	Cl3—C30—Cl1—C30i	−73.5 (6)
C11—C10—C15—C14	0.1 (3)	Cl3i—C30—Cl1—C30i	69.2 (6)
S1—C10—C15—C14	−177.1 (2)	C30i—C30—Cl1—Cl3i	−69.2 (6)
C13—C14—C15—C10	−0.2 (4)	Cl2i—C30—Cl1—Cl3i	−167.8 (7)
C3—C2—C16—C17	−103.22 (16)	Cl1i—C30—Cl1—Cl3i	−69.2 (6)
N1—C2—C16—C17	83.73 (16)	Cl2—C30—Cl1—Cl3i	−36.8 (5)
C2—C16—C17—C18	40.18 (19)	Cl3—C30—Cl1—Cl3i	−142.7 (4)
C2—C16—C17—C22	−141.19 (13)	C30i—C30—Cl2—Cl1i	−101.1 (8)
C22—C17—C18—C19	−1.8 (2)	Cl2i—C30—Cl2—Cl1i	−101.1 (8)
C16—C17—C18—C19	176.82 (13)	Cl1—C30—Cl2—Cl1i	−134.6 (6)
C17—C18—C19—C20	0.4 (2)	Cl3—C30—Cl2—Cl1i	−31.5 (6)
C18—C19—C20—O3	−177.63 (16)	Cl3i—C30—Cl2—Cl1i	−174.0 (7)
C18—C19—C20—C21	1.8 (2)	Cl2i—C30—Cl2—C30i	0.0
O3—C20—C21—O4	−2.2 (2)	Cl1i—C30—Cl2—C30i	101.1 (8)
C19—C20—C21—O4	178.36 (15)	Cl1—C30—Cl2—C30i	−33.4 (4)
O3—C20—C21—C22	176.88 (15)	Cl3—C30—Cl2—C30i	69.6 (6)
C19—C20—C21—C22	−2.6 (2)	Cl3i—C30—Cl2—C30i	−72.9 (6)
O4—C21—C22—C17	−179.85 (14)	C30i—C30—Cl2—Cl3i	72.9 (6)
C20—C21—C22—C17	1.2 (2)	Cl2i—C30—Cl2—Cl3i	72.9 (6)
C18—C17—C22—C21	1.0 (2)	Cl1i—C30—Cl2—Cl3i	174.0 (7)
C16—C17—C22—C21	−177.68 (13)	Cl1—C30—Cl2—Cl3i	39.4 (5)
C2—C3—C25—C26	26.6 (3)	Cl3—C30—Cl2—Cl3i	142.5 (4)
C4—C3—C25—C26	−154.55 (16)	C30i—C30—Cl3—Cl2i	−74.4 (5)
C3—C25—C26—C27	175.66 (15)	Cl1i—C30—Cl3—Cl2i	−146.9 (5)
C25—C26—C27—O7	1.8 (3)	Cl2—C30—Cl3—Cl2i	−129.3 (5)
C25—C26—C27—O8	−179.10 (16)	Cl1—C30—Cl3—Cl2i	−14.8 (3)
C3—C2—N1—C9	0.52 (15)	Cl3i—C30—Cl3—Cl2i	−74.4 (5)
C16—C2—N1—C9	174.73 (12)	C30i—C30—Cl3—Cl1i	72.6 (5)
C3—C2—N1—S1	171.49 (10)	Cl2i—C30—Cl3—Cl1i	146.9 (5)
C16—C2—N1—S1	−14.3 (2)	Cl2—C30—Cl3—Cl1i	17.7 (3)
C8—C9—N1—C2	178.21 (15)	Cl1—C30—Cl3—Cl1i	132.1 (4)
C4—C9—N1—C2	−1.62 (15)	Cl3i—C30—Cl3—Cl1i	72.6 (5)
C8—C9—N1—S1	6.6 (2)	Cl2i—C30—Cl3—C30i	74.4 (5)
C4—C9—N1—S1	−173.23 (10)	Cl1i—C30—Cl3—C30i	−72.6 (5)
C19—C20—O3—C23	7.7 (3)	Cl2—C30—Cl3—C30i	−54.9 (5)
C21—C20—O3—C23	−171.8 (2)	Cl1—C30—Cl3—C30i	59.5 (5)
C22—C21—O4—C24	4.9 (3)	Cl3i—C30—Cl3—C30i	0.000 (1)
C20—C21—O4—C24	−176.06 (18)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O2	0.93	2.38	2.928 (2)	118
C15—H15···O4ii	0.93	2.53	3.411 (3)	159
C16—H16A···O1	0.97	2.30	2.831 (2)	114
C24—H24B···O7iii	0.96	2.51	3.461 (2)	169
C24—H24A···O7iv	0.96	2.52	3.367 (3)	147
C25—H25···O7	0.93	2.46	2.821 (2)	103
C30—H30A···O3v	0.96	2.59	3.429 (7)	146
C30—H30A···O4v	0.96	2.55	3.424 (7)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15⋯O4i	0.93	2.53	3.411 (3)	159
C24—H24B⋯O7ii	0.96	2.51	3.461 (2)	169
C24—H24A⋯O7iii	0.96	2.52	3.367 (3)	147
C30—H30A⋯O3iv	0.96	2.59	3.429 (7)	146
C30—H30A⋯O4iv	0.96	2.55	3.424 (7)	151

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .