Crystal structure and Hirshfeld surface analysis of 3-(bromo­meth­yl)-2-[1,2-di­bromo-2-(6-nitro­benzo[d][1,3]dioxol-5-yl)eth­yl]-1-(phenyl­sulfon­yl)-1H-indole chloro­form 0.585-solvate

The title indole derivative crystallizes with a partial occupancy [0.585 (4)] CHCl₃ solvent mol­ecule. The dihedral angles between the indole ring system and pendant nitro­benzodioxolane rings system and phenyl­sulfonyl ring are 4.81 (14) and 72.24 (19)°, respectively. In the crystal, the indole mol­ecules are linked to each other and to the chloro­form mol­ecule by weak C—H...O, C—H...Cl, C—H...π, C—Br...π and C—Cl...π and aromatic π–π stacking inter­actions.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.007 Å
• Disorder in solvent or counterion
• R factor = 0.044
• wR factor = 0.134
• Data-to-parameter ratio = 16.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT041_ALERT_1_C Calc. and Reported SumFormula    Strings  Differ     Please Check
PLAT077_ALERT_4_C Unitcell Contains Non-integer Number of Atoms ..     Please Check
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.07 Report
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.2 Note
PLAT341_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00696 Ang.
PLAT971_ALERT_2_C Check Calcd Resid. Dens.  2.03Ang From C1A             2.50 eA-3

Alert level G
PLAT068_ALERT_1_G Reported F000 Differs from Calcd (or Missing)...     Please Check
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.003 Degree
PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records          1 Report
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd  2  )       100% Note
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ..... (Resd  2  )       2.92 Check
PLAT398_ALERT_2_G Deviating  C-O-C   Angle From 120 for O3       .      105.4 Degree
PLAT398_ALERT_2_G Deviating  C-O-C   Angle From 120 for O4       .      105.6 Degree
PLAT432_ALERT_2_G Short Inter X...Y Contact  Cl3      ..C13      .       3.24 Ang.
                                                   -x,-y,-z  =      2_555 Check
PLAT434_ALERT_2_G Short Inter HL..HL Contact Br1      ..Br1      .       3.46 Ang.
                                                1-x,1-y,1-z  =      2_666 Check
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         15 Note
PLAT883_ALERT_1_G No Info/Value for _atom_sites_solution_primary .     Please Do !
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         99 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          0 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   6 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  13 ALERT level G = General information/check it is not something unexpected

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   8 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   5 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: CrysAlis PRO 1.171.42.36a (Rigaku OD, 2021); cell refinement: CrysAlis PRO 1.171.42.36a (Rigaku OD, 2021); data reduction: CrysAlis PRO 1.171.42.36a (Rigaku OD, 2021); program(s) used to solve structure: SHELXT2018/2 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: Olex2 1.5 (Dolomanov et al., 2009); software used to prepare material for publication: Olex2 1.5 (Dolomanov et al., 2009).

3-(Bromomethyl)-2-[1,2-dibromo-2-(6-nitrobenzo[d][1,3]dioxol-5-yl)ethyl]-1-(phenylsulfonyl)-1H-indole chloroform 0.585-solvate

Crystal data

C24H17Br3N2O6S·0.585CHCl3	Z = 2
Mr = 771.02	F(000) = 756
Triclinic, P1	Dx = 1.859 Mg m^−3
a = 10.0987 (3) Å	Cu Kα radiation, λ = 1.54184 Å
b = 12.2744 (4) Å	Cell parameters from 10304 reflections
c = 12.4842 (5) Å	θ = 3.8–77.3°
α = 99.448 (3)°	µ = 8.09 mm^−1
β = 110.701 (3)°	T = 100 K
γ = 100.696 (3)°	Block, yellow
V = 1377.27 (9) Å^3	0.09 × 0.07 × 0.04 mm

Data collection

SuperNova, Dual, Cu at home/near, HyPix diffractometer	5783 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source	5068 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.058
Detector resolution: 10.0000 pixels mm^-1	θmax = 77.8°, θmin = 3.8°
ω scans	h = −12→12
Absorption correction: gaussian (CrysAlisPro; Rigaku OD, 2021)	k = −15→15
Tmin = 0.679, Tmax = 0.918	l = −15→15
32306 measured reflections

Refinement

Refinement on F^2	15 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.044	H-atom parameters constrained
wR(F^2) = 0.134	w = 1/[σ^2(Fo^2) + (0.0756P)^2 + 3.2347P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max = 0.001
5783 reflections	Δρmax = 2.45 e Å^−3
362 parameters	Δρmin = −1.18 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)
Br1	0.58451 (5)	0.42132 (3)	0.59315 (4)	0.02570 (13)
Br2	0.73154 (5)	0.14955 (4)	0.79206 (4)	0.02939 (13)
Br3	1.00762 (5)	0.56830 (4)	0.86622 (4)	0.02920 (13)
S1	0.68128 (11)	0.12626 (8)	0.41364 (8)	0.0223 (2)
O2	0.6345 (3)	0.0430 (2)	0.4695 (3)	0.0253 (6)
O4	0.1132 (3)	0.1454 (3)	0.7754 (3)	0.0330 (7)
O1	0.7479 (3)	0.0973 (2)	0.3329 (3)	0.0262 (6)
O3	0.1207 (3)	0.0964 (3)	0.5903 (3)	0.0274 (6)
O6	0.6713 (3)	0.4960 (3)	0.9228 (3)	0.0280 (6)
O5	0.6049 (4)	0.4185 (3)	1.0457 (3)	0.0343 (7)
N1	0.8057 (4)	0.2367 (3)	0.5219 (3)	0.0218 (7)
N2	0.5943 (4)	0.4196 (3)	0.9449 (3)	0.0252 (7)
C20	0.2451 (5)	0.2022 (4)	0.7782 (4)	0.0257 (8)
C19	0.2496 (4)	0.1717 (3)	0.6678 (4)	0.0231 (8)
C2	0.9429 (5)	0.3497 (3)	0.7066 (4)	0.0229 (8)
C9	0.5355 (5)	0.1832 (3)	0.3452 (4)	0.0242 (8)
C8	1.1596 (5)	0.4418 (4)	0.6586 (4)	0.0243 (8)
H8	1.219006	0.487579	0.736352	0.029*
C10	0.5593 (5)	0.2662 (4)	0.2858 (4)	0.0272 (8)
H10	0.651715	0.290181	0.281265	0.033*
C24	1.0022 (5)	0.4044 (4)	0.8361 (4)	0.0259 (8)
H24A	1.102550	0.395934	0.874397	0.031*
H24B	0.939908	0.364847	0.871497	0.031*
C16	0.6285 (4)	0.3342 (3)	0.7156 (3)	0.0215 (7)
H16	0.708992	0.384543	0.790336	0.026*
C15	0.6810 (5)	0.2339 (3)	0.6679 (4)	0.0221 (8)
H15	0.598316	0.182040	0.595478	0.027*
C21	0.3578 (5)	0.2820 (4)	0.8701 (4)	0.0275 (9)
H21	0.354011	0.304239	0.945258	0.033*
C7	1.2061 (5)	0.4458 (4)	0.5668 (4)	0.0277 (9)
H7	1.298673	0.494833	0.581795	0.033*
C4	0.9377 (4)	0.3002 (3)	0.5193 (4)	0.0227 (8)
C3	1.0226 (4)	0.3683 (3)	0.6332 (4)	0.0228 (8)
C17	0.4909 (5)	0.2960 (3)	0.7380 (4)	0.0224 (8)
C22	0.4805 (5)	0.3296 (3)	0.8468 (4)	0.0232 (8)
C18	0.3703 (5)	0.2154 (3)	0.6456 (4)	0.0232 (8)
H18	0.372040	0.191755	0.569903	0.028*
C23	0.0388 (5)	0.0681 (4)	0.6607 (4)	0.0278 (8)
H23A	−0.062233	0.075806	0.623430	0.033*
H23B	0.032817	−0.011831	0.667024	0.033*
C6	1.1179 (5)	0.3783 (4)	0.4524 (4)	0.0272 (9)
H6	1.151707	0.383937	0.390962	0.033*
C1	0.8102 (5)	0.2724 (3)	0.6378 (4)	0.0228 (8)
C5	0.9823 (5)	0.3031 (4)	0.4253 (4)	0.0261 (8)
H5	0.923686	0.256456	0.347776	0.031*
C11	0.4463 (6)	0.3134 (4)	0.2336 (4)	0.0345 (10)
H11	0.460782	0.370752	0.193161	0.041*
C14	0.4009 (5)	0.1455 (4)	0.3522 (4)	0.0296 (9)
H14	0.386714	0.088451	0.393030	0.036*
C12	0.3110 (6)	0.2768 (4)	0.2402 (5)	0.0390 (11)
H12	0.233581	0.309611	0.204504	0.047*
C13	0.2885 (6)	0.1925 (4)	0.2988 (5)	0.0397 (11)
H13	0.195483	0.167228	0.302029	0.048*
Cl2	0.3028 (5)	0.0547 (3)	0.0343 (3)	0.0840 (13)	0.585 (4)
Cl3	0.0526 (5)	−0.1122 (4)	−0.1145 (5)	0.1007 (15)	0.585 (4)
Cl1	0.3205 (5)	−0.1710 (3)	−0.0639 (3)	0.0828 (13)	0.585 (4)
C1A	0.247 (2)	−0.0539 (11)	−0.0772 (11)	0.079 (4)	0.585 (4)
H1A	0.257878	−0.026390	−0.145381	0.094*	0.585 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0364 (2)	0.0205 (2)	0.0333 (2)	0.00951 (17)	0.02579 (19)	0.01161 (17)
Br2	0.0408 (3)	0.0259 (2)	0.0337 (2)	0.01040 (18)	0.0248 (2)	0.01486 (19)
Br3	0.0391 (3)	0.0254 (2)	0.0270 (2)	0.00873 (18)	0.01907 (19)	0.00274 (17)
S1	0.0331 (5)	0.0168 (4)	0.0233 (4)	0.0063 (4)	0.0191 (4)	0.0041 (4)
O2	0.0382 (16)	0.0165 (13)	0.0269 (14)	0.0053 (11)	0.0206 (12)	0.0053 (11)
O4	0.0318 (16)	0.0381 (18)	0.0357 (17)	0.0024 (13)	0.0237 (14)	0.0115 (14)
O1	0.0374 (16)	0.0212 (14)	0.0280 (14)	0.0086 (12)	0.0232 (13)	0.0034 (12)
O3	0.0298 (14)	0.0230 (14)	0.0316 (15)	0.0018 (11)	0.0181 (12)	0.0050 (12)
O6	0.0329 (15)	0.0240 (14)	0.0307 (15)	0.0037 (12)	0.0210 (13)	0.0015 (12)
O5	0.0376 (17)	0.0455 (19)	0.0226 (15)	0.0078 (14)	0.0183 (13)	0.0051 (14)
N1	0.0297 (17)	0.0204 (16)	0.0213 (16)	0.0050 (13)	0.0182 (13)	0.0047 (13)
N2	0.0299 (17)	0.0273 (18)	0.0249 (17)	0.0086 (14)	0.0183 (14)	0.0049 (14)
C20	0.028 (2)	0.027 (2)	0.034 (2)	0.0084 (16)	0.0218 (17)	0.0130 (17)
C19	0.030 (2)	0.0172 (18)	0.0255 (19)	0.0051 (15)	0.0158 (16)	0.0057 (15)
C2	0.031 (2)	0.0206 (18)	0.027 (2)	0.0091 (15)	0.0207 (17)	0.0091 (16)
C9	0.035 (2)	0.0190 (18)	0.0243 (19)	0.0096 (16)	0.0176 (16)	0.0032 (15)
C8	0.0286 (19)	0.0233 (19)	0.027 (2)	0.0075 (16)	0.0183 (16)	0.0058 (16)
C10	0.039 (2)	0.0204 (19)	0.030 (2)	0.0084 (17)	0.0221 (18)	0.0064 (17)
C24	0.035 (2)	0.023 (2)	0.026 (2)	0.0053 (16)	0.0196 (17)	0.0060 (16)
C16	0.033 (2)	0.0178 (17)	0.0229 (18)	0.0071 (15)	0.0210 (16)	0.0050 (15)
C15	0.033 (2)	0.0175 (18)	0.0235 (18)	0.0068 (15)	0.0199 (16)	0.0058 (15)
C21	0.036 (2)	0.031 (2)	0.026 (2)	0.0092 (18)	0.0232 (18)	0.0101 (17)
C7	0.029 (2)	0.024 (2)	0.038 (2)	0.0053 (16)	0.0234 (18)	0.0085 (18)
C4	0.030 (2)	0.0198 (18)	0.0259 (19)	0.0078 (15)	0.0186 (16)	0.0075 (15)
C3	0.0298 (19)	0.0206 (18)	0.027 (2)	0.0096 (15)	0.0193 (16)	0.0093 (16)
C17	0.033 (2)	0.0176 (17)	0.0259 (19)	0.0069 (15)	0.0220 (17)	0.0077 (15)
C22	0.030 (2)	0.0206 (18)	0.0259 (19)	0.0059 (15)	0.0193 (16)	0.0066 (16)
C18	0.031 (2)	0.0198 (18)	0.0241 (19)	0.0069 (15)	0.0184 (16)	0.0038 (15)
C23	0.030 (2)	0.023 (2)	0.035 (2)	0.0029 (16)	0.0195 (18)	0.0078 (17)
C6	0.038 (2)	0.026 (2)	0.031 (2)	0.0103 (17)	0.0270 (18)	0.0110 (17)
C1	0.033 (2)	0.0214 (18)	0.0226 (19)	0.0074 (16)	0.0202 (16)	0.0074 (15)
C5	0.037 (2)	0.025 (2)	0.0251 (19)	0.0087 (17)	0.0216 (17)	0.0070 (16)
C11	0.052 (3)	0.025 (2)	0.036 (2)	0.015 (2)	0.026 (2)	0.0113 (19)
C14	0.041 (2)	0.0208 (19)	0.035 (2)	0.0069 (17)	0.026 (2)	0.0049 (17)
C12	0.047 (3)	0.032 (2)	0.047 (3)	0.019 (2)	0.024 (2)	0.011 (2)
C13	0.038 (2)	0.036 (3)	0.057 (3)	0.013 (2)	0.030 (2)	0.013 (2)
Cl2	0.154 (4)	0.0441 (15)	0.0602 (18)	0.0185 (18)	0.049 (2)	0.0213 (13)
Cl3	0.079 (2)	0.103 (3)	0.124 (4)	0.015 (2)	0.039 (2)	0.051 (3)
Cl1	0.175 (4)	0.082 (2)	0.0621 (17)	0.085 (2)	0.091 (2)	0.0492 (16)
C1A	0.152 (14)	0.051 (6)	0.044 (6)	0.021 (8)	0.054 (8)	0.014 (5)

Geometric parameters (Å, º)

Br1—C16	1.978 (4)	C16—H16	1.0000
Br2—C15	1.974 (4)	C16—C15	1.542 (5)
Br3—C24	1.971 (4)	C16—C17	1.519 (5)
S1—O2	1.429 (3)	C15—H15	1.0000
S1—O1	1.430 (3)	C15—C1	1.498 (5)
S1—N1	1.676 (3)	C21—H21	0.9500
S1—C9	1.754 (4)	C21—C22	1.415 (5)
O4—C20	1.369 (5)	C7—H7	0.9500
O4—C23	1.429 (6)	C7—C6	1.399 (6)
O3—C19	1.362 (5)	C4—C3	1.392 (6)
O3—C23	1.443 (5)	C4—C5	1.401 (5)
O6—N2	1.236 (5)	C17—C22	1.399 (5)
O5—N2	1.227 (5)	C17—C18	1.406 (6)
N1—C4	1.427 (5)	C18—H18	0.9500
N1—C1	1.423 (5)	C23—H23A	0.9900
N2—C22	1.459 (5)	C23—H23B	0.9900
C20—C19	1.387 (6)	C6—H6	0.9500
C20—C21	1.365 (6)	C6—C5	1.394 (6)
C19—C18	1.376 (5)	C5—H5	0.9500
C2—C24	1.494 (6)	C11—H11	0.9500
C2—C3	1.436 (5)	C11—C12	1.392 (7)
C2—C1	1.371 (6)	C14—H14	0.9500
C9—C10	1.389 (6)	C14—C13	1.378 (7)
C9—C14	1.390 (6)	C12—H12	0.9500
C8—H8	0.9500	C12—C13	1.392 (7)
C8—C7	1.388 (6)	C13—H13	0.9500
C8—C3	1.400 (6)	Cl2—C1A	1.609 (12)
C10—H10	0.9500	Cl3—C1A	1.815 (18)
C10—C11	1.380 (7)	Cl1—C1A	1.742 (15)
C24—H24A	0.9900	C1A—H1A	1.0000
C24—H24B	0.9900
O2—S1—O1	120.07 (17)	C22—C21—H21	121.9
O2—S1—N1	106.78 (17)	C8—C7—H7	119.7
O2—S1—C9	109.47 (19)	C8—C7—C6	120.7 (4)
O1—S1—N1	105.88 (17)	C6—C7—H7	119.7
O1—S1—C9	109.04 (19)	C3—C4—N1	107.0 (3)
N1—S1—C9	104.44 (18)	C3—C4—C5	122.4 (4)
C20—O4—C23	105.7 (3)	C5—C4—N1	130.5 (4)
C19—O3—C23	105.4 (3)	C8—C3—C2	131.0 (4)
C4—N1—S1	125.3 (3)	C4—C3—C2	108.6 (4)
C1—N1—S1	126.2 (3)	C4—C3—C8	120.4 (4)
C1—N1—C4	107.8 (3)	C22—C17—C16	124.1 (4)
O6—N2—C22	118.8 (3)	C22—C17—C18	118.3 (4)
O5—N2—O6	122.9 (4)	C18—C17—C16	117.4 (3)
O5—N2—C22	118.2 (3)	C21—C22—N2	114.4 (3)
O4—C20—C19	109.9 (4)	C17—C22—N2	122.5 (3)
C21—C20—O4	128.3 (4)	C17—C22—C21	123.1 (4)
C21—C20—C19	121.7 (4)	C19—C18—C17	118.2 (4)
O3—C19—C20	110.1 (3)	C19—C18—H18	120.9
O3—C19—C18	127.6 (4)	C17—C18—H18	120.9
C18—C19—C20	122.3 (4)	O4—C23—O3	107.8 (3)
C3—C2—C24	123.9 (4)	O4—C23—H23A	110.1
C1—C2—C24	128.1 (3)	O4—C23—H23B	110.1
C1—C2—C3	108.0 (4)	O3—C23—H23A	110.1
C10—C9—S1	118.3 (3)	O3—C23—H23B	110.1
C10—C9—C14	121.9 (4)	H23A—C23—H23B	108.5
C14—C9—S1	119.8 (3)	C7—C6—H6	118.8
C7—C8—H8	121.0	C5—C6—C7	122.3 (4)
C7—C8—C3	118.1 (4)	C5—C6—H6	118.8
C3—C8—H8	121.0	N1—C1—C15	122.1 (4)
C9—C10—H10	120.6	C2—C1—N1	108.5 (3)
C11—C10—C9	118.8 (4)	C2—C1—C15	129.2 (4)
C11—C10—H10	120.6	C4—C5—H5	122.0
Br3—C24—H24A	109.3	C6—C5—C4	116.0 (4)
Br3—C24—H24B	109.3	C6—C5—H5	122.0
C2—C24—Br3	111.4 (3)	C10—C11—H11	120.0
C2—C24—H24A	109.3	C10—C11—C12	119.9 (4)
C2—C24—H24B	109.3	C12—C11—H11	120.0
H24A—C24—H24B	108.0	C9—C14—H14	120.6
Br1—C16—H16	109.5	C13—C14—C9	118.8 (4)
C15—C16—Br1	106.4 (2)	C13—C14—H14	120.6
C15—C16—H16	109.5	C11—C12—H12	119.8
C17—C16—Br1	108.4 (3)	C13—C12—C11	120.5 (5)
C17—C16—H16	109.5	C13—C12—H12	119.8
C17—C16—C15	113.4 (3)	C14—C13—C12	120.1 (5)
Br2—C15—H15	108.9	C14—C13—H13	120.0
C16—C15—Br2	106.6 (3)	C12—C13—H13	120.0
C16—C15—H15	108.9	Cl2—C1A—Cl3	106.5 (9)
C1—C15—Br2	110.4 (3)	Cl2—C1A—Cl1	120.0 (9)
C1—C15—C16	112.9 (3)	Cl2—C1A—H1A	108.5
C1—C15—H15	108.9	Cl3—C1A—H1A	108.5
C20—C21—H21	121.9	Cl1—C1A—Cl3	104.4 (7)
C20—C21—C22	116.2 (4)	Cl1—C1A—H1A	108.5
Br1—C16—C15—Br2	178.14 (17)	C10—C9—C14—C13	−0.2 (7)
Br1—C16—C15—C1	56.7 (4)	C10—C11—C12—C13	−0.3 (8)
Br1—C16—C17—C22	−118.0 (4)	C24—C2—C3—C8	−4.9 (7)
Br1—C16—C17—C18	66.7 (4)	C24—C2—C3—C4	177.2 (4)
Br2—C15—C1—N1	119.7 (4)	C24—C2—C1—N1	−175.3 (4)
Br2—C15—C1—C2	−65.5 (5)	C24—C2—C1—C15	9.4 (7)
S1—N1—C4—C3	−168.6 (3)	C16—C15—C1—N1	−121.0 (4)
S1—N1—C4—C5	13.3 (6)	C16—C15—C1—C2	53.7 (6)
S1—N1—C1—C2	168.0 (3)	C16—C17—C22—N2	10.0 (6)
S1—N1—C1—C15	−16.3 (6)	C16—C17—C22—C21	−171.8 (4)
S1—C9—C10—C11	−178.7 (3)	C16—C17—C18—C19	174.1 (4)
S1—C9—C14—C13	179.3 (4)	C15—C16—C17—C22	124.1 (4)
O2—S1—N1—C4	139.8 (3)	C15—C16—C17—C18	−51.3 (5)
O2—S1—N1—C1	−30.3 (4)	C21—C20—C19—O3	−176.2 (4)
O2—S1—C9—C10	179.9 (3)	C21—C20—C19—C18	3.4 (7)
O2—S1—C9—C14	0.4 (4)	C7—C8—C3—C2	−176.6 (4)
O4—C20—C19—O3	1.0 (5)	C7—C8—C3—C4	1.1 (6)
O4—C20—C19—C18	−179.4 (4)	C7—C6—C5—C4	1.1 (6)
O4—C20—C21—C22	−178.1 (4)	C4—N1—C1—C2	−3.5 (4)
O1—S1—N1—C4	10.7 (4)	C4—N1—C1—C15	172.2 (4)
O1—S1—N1—C1	−159.3 (3)	C3—C2—C24—Br3	73.2 (5)
O1—S1—C9—C10	−47.0 (4)	C3—C2—C1—N1	2.6 (5)
O1—S1—C9—C14	133.6 (3)	C3—C2—C1—C15	−172.7 (4)
O3—C19—C18—C17	177.7 (4)	C3—C8—C7—C6	0.1 (6)
O6—N2—C22—C21	−150.6 (4)	C3—C4—C5—C6	0.1 (6)
O6—N2—C22—C17	27.7 (6)	C17—C16—C15—Br2	−62.8 (4)
O5—N2—C22—C21	26.3 (5)	C17—C16—C15—C1	175.8 (3)
O5—N2—C22—C17	−155.4 (4)	C22—C17—C18—C19	−1.5 (6)
N1—S1—C9—C10	65.9 (4)	C18—C17—C22—N2	−174.7 (4)
N1—S1—C9—C14	−113.6 (3)	C18—C17—C22—C21	3.5 (6)
N1—C4—C3—C2	−1.4 (4)	C23—O4—C20—C19	5.7 (5)
N1—C4—C3—C8	−179.5 (4)	C23—O4—C20—C21	−177.4 (4)
N1—C4—C5—C6	178.0 (4)	C23—O3—C19—C20	−7.1 (4)
C20—O4—C23—O3	−10.0 (4)	C23—O3—C19—C18	173.3 (4)
C20—C19—C18—C17	−1.8 (6)	C1—N1—C4—C3	2.9 (4)
C20—C21—C22—N2	176.4 (4)	C1—N1—C4—C5	−175.1 (4)
C20—C21—C22—C17	−1.9 (6)	C1—C2—C24—Br3	−109.2 (4)
C19—O3—C23—O4	10.5 (4)	C1—C2—C3—C8	177.1 (4)
C19—C20—C21—C22	−1.5 (6)	C1—C2—C3—C4	−0.8 (5)
C9—S1—N1—C4	−104.3 (3)	C5—C4—C3—C2	176.9 (4)
C9—S1—N1—C1	85.7 (4)	C5—C4—C3—C8	−1.3 (6)
C9—C10—C11—C12	−0.5 (7)	C11—C12—C13—C14	0.9 (8)
C9—C14—C13—C12	−0.6 (7)	C14—C9—C10—C11	0.8 (6)
C8—C7—C6—C5	−1.3 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O5^i	0.95	2.58	3.525 (6)	170
C13—H13···Cl13^ii	0.95	2.63	3.244 (8)	123
C14—H14···O2^iii	0.95	2.57	3.518 (6)	172
C1A—H1A···O1^iv	1.00	2.34	3.169 (15)	140
C5—H5···O1	0.95	2.32	2.865 (6)	116
C15—H15···O2	1.00	2.30	2.950 (5)	122
C16—H16···O6	1.00	2.16	2.832 (5)	123
C24—H24B···Br2	0.99	2.83	3.572 (4)	132

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