Iodo-nitroarenesulfonamides: interplay of hard and soft hydrogen bonds, I...O interactions and aromatic π...π stacking interactions

Molecules of N-(4′-iodophenylsulfonyl)-4-nitroaniline, 4-O₂NC₆H₄NHSO₂C₆H₄I-4′ (1), are linked by three-centre I...O₂N interactions into chains and these chains are linked into a three-dimensional framework by C—H...O hydrogen bonds. In the isomeric N-(4′-nitrophenylsulfonyl)-4-iodoaniline, 4-IC₆H₄NHSO₂C₆H₄NO₂-4′ (2), the chains generated by the I...O₂N interactions are again linked into a three-dimensional framework by C—H...O hydrogen bonds. Molecules of N,N-bis(3′-nitrophenylsulfonyl)-4-iodoaniline, 4-IC₆H₄N(SO₂C₆H₄NO₂-3′)₂ (3), lie across twofold rotation axes in space group C2/c and they are linked into chains by paired I...O=S interactions: these chains are linked into sheets by a C—H...O hydrogen bond, and the sheets are linked into a three-dimensional framework by aromatic π...π stacking interactions. In N-(4′-iodophenylsulfonyl)-3-nitroaniline, 3-O₂NC₆H₄NHSO₂C₆H₄I-4′ (4), there are rings formed by hard N—H...O=S hydrogen bonds and rings formed by two-centre I...nitro interactions, which together generate a chain of fused rings: the combination of a C—H...O hydrogen bond and aromatic π...π stacking interactions links the chains into sheets. Molecules of N-(4′-iodophenylsulfonyl)-4-methyl-2-nitroaniline, 4-CH₃-2-O₂NC₆H₃NHSO₂C₆H₄I-4′ (5), are linked by N—H...O=S and C—H...O(nitro) hydrogen bonds into a chain containing alternating and rings, but there are no I...O interactions of either type. There are two molecules in the asymmetric unit of N-(4′-iodophenylsulfonyl)-2-nitroaniline, 2-O₂NC₆H₄NHSO₂C₆H₄I-4′ (6), and the combination of an I...O=S interaction and a hard N—H...O(nitro) hydrogen bond links the two types of molecule to form a cyclic, centrosymmetric four-component aggregate. C—H...O hydrogen bonds link these four-molecule aggregates to form a molecular ladder. Comparisons are made with structures retrieved from the Cambridge Structural Database.

Computing details

For all compounds, data collection: Kappa-CCD server software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997b); molecular graphics: PLATON (Spek, 2001); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997b) and PRPKAPPA (Ferguson, 1999).

(I) N-(4'-Iodophenylsulfonyl)-4-nitroaniline

Crystal data

C12H9IN2O4S	F(000) = 784
Mr = 404.17	Dx = 1.971 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 5.0825 (1) Å	Cell parameters from 3088 reflections
b = 13.0448 (3) Å	θ = 3.1–27.5°
c = 20.5648 (6) Å	µ = 2.52 mm^−1
β = 92.7786 (9)°	T = 150 K
V = 1361.85 (6) Å^3	Plate, colourless
Z = 4	0.30 × 0.18 × 0.08 mm

Data collection

Kappa-CCD diffractometer	3088 independent reflections
Radiation source: fine-focus sealed X-ray tube	2691 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.066
φ scans, and ω scans with κ offsets	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = −6→6
Tmin = 0.519, Tmax = 0.824	k = −16→16
12123 measured reflections	l = −26→26

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.096	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0562P)^2 + 0.6779P] where P = (Fo^2 + 2Fc^2)/3
3088 reflections	(Δ/σ)max < 0.001
181 parameters	Δρmax = 0.96 e Å^−3
0 restraints	Δρmin = −1.33 e Å^−3

Special details

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.33544 (12)	0.25798 (5)	0.23238 (4)	0.01846 (17)
O11	0.4056 (4)	0.16297 (16)	0.20329 (12)	0.0253 (5)
O12	0.0713 (4)	0.27424 (16)	0.25234 (11)	0.0257 (5)
N1	0.5314 (4)	0.27071 (18)	0.29794 (12)	0.0188 (5)
C11	0.4989 (6)	0.35990 (19)	0.33739 (16)	0.0184 (6)
C12	0.6624 (5)	0.4451 (2)	0.33071 (15)	0.0229 (6)
C13	0.6240 (6)	0.5318 (2)	0.36729 (16)	0.0235 (6)
C14	0.4212 (6)	0.5326 (2)	0.40963 (15)	0.0206 (6)
N2	0.3676 (6)	0.6263 (2)	0.44585 (15)	0.0270 (6)
O21	0.1784 (6)	0.62793 (19)	0.48041 (16)	0.0451 (7)
O22	0.5151 (5)	0.69990 (19)	0.44074 (14)	0.0441 (7)
C15	0.2609 (6)	0.4483 (2)	0.41836 (15)	0.0230 (6)
C16	0.3024 (6)	0.3611 (2)	0.38185 (17)	0.0228 (7)
C21	0.4173 (6)	0.3591 (2)	0.18035 (16)	0.0188 (6)
C22	0.6164 (6)	0.3432 (2)	0.13800 (16)	0.0235 (6)
C23	0.7014 (6)	0.4246 (2)	0.10049 (16)	0.0249 (6)
C24	0.5853 (6)	0.5199 (2)	0.10668 (14)	0.0220 (6)
I1	0.71053 (4)	0.641812 (15)	0.049127 (10)	0.02947 (11)
C25	0.3862 (6)	0.5355 (2)	0.14893 (17)	0.0271 (7)
C26	0.3009 (6)	0.4553 (2)	0.18641 (16)	0.0259 (6)
H1	0.6520	0.2244	0.3084	0.023*
H12	0.7996	0.4432	0.3010	0.028*
H13	0.7348	0.5899	0.3635	0.028*
H15	0.1257	0.4503	0.4487	0.028*
H16	0.1963	0.3020	0.3873	0.027*
H22	0.6946	0.2774	0.1345	0.028*
H23	0.8374	0.4148	0.0710	0.030*
H25	0.3079	0.6013	0.1522	0.032*
H26	0.1650	0.4655	0.2159	0.031*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0142 (3)	0.0159 (3)	0.0255 (4)	−0.0009 (3)	0.0042 (3)	−0.0014 (3)
O11	0.0266 (11)	0.0175 (10)	0.0322 (13)	−0.0023 (9)	0.0065 (9)	−0.0035 (9)
O12	0.0126 (9)	0.0271 (11)	0.0378 (13)	−0.0010 (8)	0.0061 (8)	−0.0006 (9)
N1	0.0156 (10)	0.0156 (11)	0.0256 (14)	0.0044 (9)	0.0034 (9)	0.0000 (9)
C11	0.0181 (13)	0.0156 (14)	0.0217 (16)	0.0024 (10)	0.0017 (12)	0.0030 (10)
C12	0.0175 (12)	0.0242 (15)	0.0279 (17)	−0.0025 (12)	0.0096 (11)	−0.0014 (12)
C13	0.0203 (13)	0.0174 (14)	0.0334 (17)	−0.0058 (11)	0.0085 (12)	0.0022 (12)
C14	0.0229 (13)	0.0169 (13)	0.0222 (15)	0.0011 (11)	0.0038 (11)	−0.0001 (11)
N2	0.0304 (13)	0.0197 (13)	0.0317 (17)	−0.0002 (11)	0.0093 (12)	−0.0003 (11)
O21	0.0503 (16)	0.0301 (14)	0.058 (2)	−0.0075 (11)	0.0350 (14)	−0.0135 (12)
O22	0.0542 (15)	0.0237 (12)	0.0569 (17)	−0.0182 (12)	0.0287 (13)	−0.0107 (11)
C15	0.0211 (13)	0.0239 (15)	0.0248 (17)	−0.0037 (12)	0.0096 (12)	0.0013 (12)
C16	0.0219 (14)	0.0204 (16)	0.0267 (18)	−0.0046 (11)	0.0069 (13)	0.0028 (11)
C21	0.0181 (13)	0.0177 (15)	0.0208 (16)	−0.0008 (10)	0.0024 (12)	−0.0002 (10)
C22	0.0256 (15)	0.0183 (14)	0.0274 (18)	0.0048 (12)	0.0080 (13)	−0.0009 (12)
C23	0.0264 (14)	0.0220 (15)	0.0266 (17)	0.0019 (12)	0.0063 (12)	0.0015 (12)
C24	0.0270 (14)	0.0209 (14)	0.0180 (15)	−0.0051 (12)	0.0005 (11)	0.0004 (11)
I1	0.04171 (17)	0.02133 (16)	0.02538 (17)	−0.00558 (8)	0.00187 (11)	0.00356 (7)
C25	0.0299 (15)	0.0193 (14)	0.0321 (18)	0.0067 (12)	0.0025 (13)	0.0006 (12)
C26	0.0256 (14)	0.0218 (15)	0.0309 (18)	0.0047 (12)	0.0077 (12)	−0.0016 (13)

Geometric parameters (Å, º)

S1—O11	1.429 (2)	N2—O22	1.226 (4)
S1—O12	1.438 (2)	C15—C16	1.385 (4)
S1—N1	1.645 (3)	C15—H15	0.9500
S1—C21	1.760 (3)	C16—H16	0.9500
N1—C11	1.433 (4)	C21—C22	1.382 (4)
N1—H1	0.8800	C21—C26	1.396 (4)
C11—C16	1.386 (4)	C22—C23	1.393 (4)
C11—C12	1.398 (4)	C22—H22	0.9500
C12—C13	1.378 (4)	C23—C24	1.384 (4)
C12—H12	0.9500	C23—H23	0.9500
C13—C14	1.381 (4)	C24—C25	1.381 (4)
C13—H13	0.9500	C24—I1	2.100 (3)
C14—C15	1.385 (4)	C25—C26	1.382 (4)
C14—N2	1.464 (4)	C25—H25	0.9500
N2—O21	1.223 (4)	C26—H26	0.9500
O11—S1—O12	120.17 (13)	C16—C15—C14	118.4 (3)
O11—S1—N1	106.09 (13)	C16—C15—H15	120.8
O12—S1—N1	106.71 (13)	C14—C15—H15	120.8
O11—S1—C21	108.92 (14)	C15—C16—C11	120.0 (3)
O12—S1—C21	108.31 (13)	C15—C16—H16	120.0
N1—S1—C21	105.72 (13)	C11—C16—H16	120.0
C11—N1—S1	117.65 (18)	C22—C21—C26	121.1 (3)
C11—N1—H1	121.2	C22—C21—S1	118.2 (2)
S1—N1—H1	121.2	C26—C21—S1	120.4 (2)
C16—C11—C12	120.4 (3)	C21—C22—C23	119.4 (3)
C16—C11—N1	119.3 (2)	C21—C22—H22	120.3
C12—C11—N1	120.3 (3)	C23—C22—H22	120.3
C13—C12—C11	119.9 (3)	C24—C23—C22	119.2 (3)
C13—C12—H12	120.1	C24—C23—H23	120.4
C11—C12—H12	120.1	C22—C23—H23	120.4
C12—C13—C14	118.7 (3)	C25—C24—C23	121.3 (3)
C12—C13—H13	120.7	C25—C24—I1	119.6 (2)
C14—C13—H13	120.7	C23—C24—I1	119.1 (2)
C13—C14—C15	122.5 (3)	C24—C25—C26	119.9 (3)
C13—C14—N2	119.3 (3)	C24—C25—H25	120.1
C15—C14—N2	118.1 (3)	C26—C25—H25	120.1
O21—N2—O22	122.5 (3)	C25—C26—C21	119.0 (3)
O21—N2—C14	118.7 (3)	C25—C26—H26	120.5
O22—N2—C14	118.7 (3)	C21—C26—H26	120.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O11^i	0.95	2.53	3.330 (4)	143
C15—H15···O21^ii	0.95	2.40	3.280 (4)	153
C22—H22···O22^iii	0.95	2.41	3.149 (4)	134

Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2; (ii) −x, −y+1, −z+1; (iii) −x+3/2, y−1/2, −z+1/2.

(II) N-(4'-Nitrophenylsulfonyl)-4-iodoaniline

Crystal data

C12H9IN2O4S	F(000) = 784
Mr = 404.17	Dx = 1.971 Mg m^−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
a = 5.0246 (1) Å	Cell parameters from 2659 reflections
b = 13.0735 (4) Å	θ = 2.0–28.3°
c = 20.8840 (6) Å	µ = 2.52 mm^−1
β = 96.8350 (13)°	T = 150 K
V = 1362.10 (6) Å^3	Block, colourless
Z = 4	0.30 × 0.20 × 0.10 mm

Data collection

Kappa-CCD diffractometer	2659 independent reflections
Radiation source: fine-focus sealed X-ray tube	2610 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.061
φ scans, and ω scans with κ offsets	θmax = 28.3°, θmin = 2.0°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = −6→5
Tmin = 0.519, Tmax = 0.787	k = −16→16
7110 measured reflections	l = −27→26

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.028	w = 1/[σ^2(Fo^2) + (0.0535P)^2 + 0.5195P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.084	(Δ/σ)max < 0.001
S = 1.12	Δρmax = 0.73 e Å^−3
2659 reflections	Δρmin = −0.99 e Å^−3
182 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
2 restraints	Extinction coefficient: 0.0083 (6)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 948 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.00 (2)

Special details

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
I4	1.00189 (6)	0.165320 (18)	0.50040 (3)	0.02354 (13)
C11	0.7962 (9)	−0.1346 (4)	0.6261 (2)	0.0163 (8)
C12	0.6522 (9)	−0.0447 (4)	0.6337 (2)	0.0213 (9)
C13	0.7072 (10)	0.0412 (4)	0.5972 (2)	0.0241 (10)
C14	0.9056 (10)	0.0361 (3)	0.5541 (2)	0.0200 (9)
C15	1.0498 (10)	−0.0543 (4)	0.5463 (2)	0.0221 (9)
C16	0.9911 (10)	−0.1390 (4)	0.5826 (2)	0.0222 (9)
N1	0.7456 (7)	−0.2241 (3)	0.66379 (18)	0.0167 (7)
S1	0.93999 (18)	−0.24372 (7)	0.72887 (5)	0.0146 (2)
O11	0.8585 (7)	−0.3395 (2)	0.75508 (19)	0.0197 (7)
O12	1.2101 (6)	−0.2303 (3)	0.71241 (16)	0.0209 (6)
C21	0.8647 (9)	−0.1437 (4)	0.7818 (2)	0.0155 (8)
C22	0.6656 (10)	−0.1589 (3)	0.8240 (2)	0.0167 (9)
C23	0.5855 (9)	−0.0775 (4)	0.8606 (2)	0.0179 (8)
C24	0.7111 (9)	0.0156 (3)	0.8544 (2)	0.0176 (8)
C25	0.9115 (9)	0.0317 (4)	0.8136 (2)	0.0213 (9)
C26	0.9925 (9)	−0.0499 (3)	0.7769 (2)	0.0190 (9)
N2	0.6249 (8)	0.1034 (3)	0.89235 (19)	0.0221 (8)
O21	0.4278 (9)	0.0929 (3)	0.9229 (2)	0.0411 (10)
O22	0.7493 (10)	0.1840 (3)	0.8900 (2)	0.0349 (10)
H12	0.5209	−0.0419	0.6629	0.026*
H13	0.6113	0.1030	0.6012	0.029*
H15	1.1821	−0.0575	0.5175	0.027*
H16	1.0844	−0.2013	0.5781	0.027*
H1	0.6127	−0.2661	0.6513	0.020*
H22	0.5871	−0.2245	0.8273	0.020*
H23	0.4509	−0.0856	0.8885	0.021*
H25	0.9909	0.0973	0.8109	0.026*
H26	1.1297	−0.0416	0.7497	0.023*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I4	0.03314 (19)	0.02021 (16)	0.01701 (16)	−0.00546 (12)	0.00193 (10)	0.00258 (11)
C11	0.016 (2)	0.019 (2)	0.014 (2)	−0.0039 (17)	0.0027 (16)	−0.0017 (17)
C12	0.022 (2)	0.021 (2)	0.022 (2)	0.0035 (17)	0.0099 (17)	0.0020 (17)
C13	0.026 (2)	0.022 (2)	0.025 (2)	0.0036 (18)	0.0069 (18)	0.0033 (19)
C14	0.028 (2)	0.016 (2)	0.0151 (19)	−0.0034 (17)	−0.0005 (16)	0.0001 (15)
C15	0.026 (2)	0.021 (2)	0.021 (2)	−0.0028 (18)	0.0094 (18)	0.0007 (17)
C16	0.027 (3)	0.019 (2)	0.022 (2)	−0.0003 (19)	0.0104 (19)	−0.0019 (18)
N1	0.0127 (16)	0.0191 (18)	0.0181 (17)	−0.0040 (14)	0.0017 (13)	0.0008 (14)
S1	0.0122 (4)	0.0136 (4)	0.0186 (4)	0.0001 (3)	0.0040 (3)	0.0001 (4)
O11	0.0198 (19)	0.0151 (18)	0.0246 (19)	0.0014 (10)	0.0045 (14)	0.0020 (11)
O12	0.0145 (15)	0.0227 (16)	0.0264 (16)	0.0021 (12)	0.0059 (12)	−0.0003 (13)
C21	0.013 (2)	0.0188 (18)	0.014 (2)	0.0011 (16)	0.0000 (16)	−0.0003 (16)
C22	0.020 (2)	0.014 (2)	0.016 (2)	−0.0029 (15)	0.0058 (18)	0.0029 (14)
C23	0.018 (2)	0.022 (2)	0.0145 (18)	0.0001 (17)	0.0060 (15)	0.0020 (16)
C24	0.025 (2)	0.015 (2)	0.0137 (18)	0.0007 (17)	0.0035 (16)	−0.0016 (15)
C25	0.022 (2)	0.017 (2)	0.026 (2)	−0.0033 (17)	0.0057 (18)	−0.0034 (17)
C26	0.019 (2)	0.017 (2)	0.023 (2)	−0.0023 (16)	0.0102 (17)	0.0012 (17)
N2	0.030 (2)	0.0188 (19)	0.0183 (17)	−0.0002 (15)	0.0077 (15)	−0.0019 (14)
O21	0.053 (3)	0.033 (2)	0.044 (2)	−0.0058 (19)	0.034 (2)	−0.0089 (19)
O22	0.044 (3)	0.0237 (18)	0.041 (3)	−0.0085 (17)	0.018 (2)	−0.0114 (17)

Geometric parameters (Å, º)

I4—C14	2.115 (4)	S1—O12	1.450 (3)
C11—C12	1.399 (7)	S1—C21	1.782 (5)
C11—C16	1.414 (6)	C21—C26	1.394 (6)
C11—N1	1.449 (6)	C21—C22	1.424 (6)
C12—C13	1.404 (7)	C22—C23	1.397 (6)
C12—H12	0.9500	C22—H22	0.9500
C13—C14	1.422 (6)	C23—C24	1.384 (6)
C13—H13	0.9500	C23—H23	0.9500
C14—C15	1.406 (7)	C24—C25	1.410 (6)
C15—C16	1.393 (7)	C24—N2	1.489 (6)
C15—H15	0.9500	C25—C26	1.401 (6)
C16—H16	0.9500	C25—H25	0.9500
N1—S1	1.597 (4)	C26—H26	0.9500
N1—H1	0.8800	N2—O22	1.229 (6)
S1—O11	1.445 (3)	N2—O21	1.248 (6)
C12—C11—C16	120.9 (4)	O11—S1—C21	108.1 (2)
C12—C11—N1	119.4 (4)	O12—S1—C21	109.4 (2)
C16—C11—N1	119.7 (4)	N1—S1—C21	104.8 (2)
C11—C12—C13	118.2 (4)	C26—C21—C22	122.1 (4)
C11—C12—H12	120.9	C26—C21—S1	117.8 (3)
C13—C12—H12	120.9	C22—C21—S1	119.9 (3)
C12—C13—C14	120.4 (5)	C23—C22—C21	120.1 (4)
C12—C13—H13	119.8	C23—C22—H22	119.9
C14—C13—H13	119.8	C21—C22—H22	119.9
C15—C14—C13	121.4 (4)	C24—C23—C22	117.0 (4)
C15—C14—I4	117.2 (3)	C24—C23—H23	121.5
C13—C14—I4	121.3 (4)	C22—C23—H23	121.5
C16—C15—C14	117.4 (4)	C23—C24—C25	123.7 (4)
C16—C15—H15	121.3	C23—C24—N2	117.6 (4)
C14—C15—H15	121.3	C25—C24—N2	118.7 (4)
C15—C16—C11	121.7 (5)	C26—C25—C24	119.4 (4)
C15—C16—H16	119.2	C26—C25—H25	120.3
C11—C16—H16	119.2	C24—C25—H25	120.3
C11—N1—S1	117.6 (3)	C21—C26—C25	117.6 (4)
C11—N1—H1	121.2	C21—C26—H26	121.2
S1—N1—H1	121.2	C25—C26—H26	121.2
O11—S1—O12	120.7 (2)	O22—N2—O21	123.7 (4)
O11—S1—N1	106.8 (2)	O22—N2—C24	117.2 (4)
O12—S1—N1	105.88 (19)	O21—N2—C24	119.1 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···O21^i	0.95	2.49	3.416 (6)	164
C25—H25···O11^ii	0.95	2.44	3.167 (6)	133

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

(III) N,N-Bis(3'-nitrophenylsulfonyl)-4-iodoaniline

Crystal data

C18H12IN3O8S2	F(000) = 1160
Mr = 589.33	Dx = 1.862 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 18.1057 (4) Å	Cell parameters from 2378 reflections
b = 11.3671 (3) Å	θ = 3.3–27.5°
c = 11.1174 (3) Å	µ = 1.78 mm^−1
β = 113.2717 (16)°	T = 150 K
V = 2101.91 (9) Å^3	Plate, colourless
Z = 4	0.10 × 0.09 × 0.07 mm

Data collection

Kappa-CCD diffractometer	2378 independent reflections
Radiation source: fine-focus sealed X-ray tube	2154 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
φ scans, and ω scans with κ offsets	θmax = 27.5°, θmin = 3.3°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = −23→23
Tmin = 0.843, Tmax = 0.886	k = −13→14
6830 measured reflections	l = −14→14

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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.065	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0238P)^2 + 2.5253P] where P = (Fo^2 + 2Fc^2)/3
2378 reflections	(Δ/σ)max < 0.001
147 parameters	Δρmax = 0.44 e Å^−3
0 restraints	Δρmin = −0.60 e Å^−3

Special details

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
I4	0.0000	1.034511 (17)	0.7500	0.03694 (10)
C14	0.0000	0.8499 (2)	0.7500	0.0203 (6)
C13	−0.03212 (13)	0.79050 (19)	0.6317 (2)	0.0222 (4)
C12	−0.03245 (12)	0.66814 (18)	0.63154 (19)	0.0186 (4)
C11	0.0000	0.60872)	0.7500	0.0138 (5)
N1	0.0000	0.48100 (19)	0.7500	0.0129 (5)
S1	0.07764 (3)	0.41170 (4)	0.73402 (4)	0.01294 (12)
O11	0.05182 (8)	0.29598 (12)	0.68591 (13)	0.0167 (3)
O12	0.10607 (9)	0.49075 (13)	0.66201 (14)	0.0185 (3)
C21	0.15084 (11)	0.40360 (17)	0.89520 (19)	0.0147 (4)
C22	0.14594 (12)	0.31489 (17)	0.97801 (19)	0.0161 (4)
C23	0.20415 (12)	0.31499 (18)	1.10426 (19)	0.0173 (4)
C24	0.26592 (13)	0.3965 (2)	1.1489 (2)	0.0209 (4)
C25	0.26907 (13)	0.4834 (2)	1.0637 (2)	0.0215 (4)
C26	0.21133 (12)	0.48820 (19)	0.9370 (2)	0.0185 (4)
N2	0.19919 (12)	0.22469 (17)	1.19610 (17)	0.0239 (4)
O21	0.24218 (13)	0.23785 (17)	1.31267 (16)	0.0436 (5)
O22	0.15254 (10)	0.14245 (15)	1.15197 (16)	0.0297 (4)
H13	−0.0537	0.8329	0.5516	0.027*
H12	−0.0546	0.6259	0.5514	0.022*
H22	0.1047	0.2571	0.9492	0.019*
H24	0.3053	0.3929	1.2361	0.025*
H25	0.3111	0.5400	1.0924	0.026*
H26	0.2130	0.5487	0.8791	0.022*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I4	0.02060 (13)	0.00679 (12)	0.06531 (18)	0.000	−0.00240 (11)	0.000
C14	0.0153 (14)	0.0075 (13)	0.0368 (17)	0.000	0.0088 (13)	0.000
C13	0.0254 (11)	0.0127 (10)	0.0261 (11)	0.0017 (8)	0.0074 (9)	0.0079 (8)
C12	0.0228 (10)	0.0135 (10)	0.0177 (9)	−0.0004 (8)	0.0059 (8)	0.0000 (8)
C11	0.0172 (13)	0.0071 (12)	0.0173 (13)	0.000	0.0071 (11)	0.000
N1	0.0157 (11)	0.0068 (11)	0.0182 (11)	0.000	0.0089 (9)	0.000
S1	0.0162 (2)	0.0092 (2)	0.0155 (2)	−0.00028 (17)	0.00847 (19)	−0.00088 (17)
O11	0.0219 (7)	0.0096 (7)	0.0201 (7)	0.0000 (6)	0.0099 (6)	−0.0032 (5)
O12	0.0233 (8)	0.0160 (7)	0.0210 (7)	−0.0018 (6)	0.0138 (6)	0.0018 (6)
C21	0.0155 (9)	0.0114 (9)	0.0185 (9)	0.0031 (7)	0.0080 (8)	−0.0026 (7)
C22	0.0171 (9)	0.0124 (9)	0.0208 (10)	0.0031 (8)	0.0096 (8)	−0.0014 (8)
C23	0.0210 (10)	0.0157 (10)	0.0187 (9)	0.0070 (8)	0.0115 (8)	0.0008 (8)
C24	0.0176 (10)	0.0234 (11)	0.0193 (10)	0.0056 (9)	0.0049 (8)	−0.0041 (8)
C25	0.0165 (10)	0.0195 (11)	0.0279 (11)	−0.0015 (8)	0.0081 (9)	−0.0072 (9)
C26	0.0184 (10)	0.0126 (9)	0.0253 (10)	0.0015 (8)	0.0096 (9)	−0.0006 (8)
N2	0.0281 (10)	0.0224 (10)	0.0222 (9)	0.0092 (8)	0.0110 (8)	0.0049 (8)
O21	0.0622 (14)	0.0390 (11)	0.0194 (8)	−0.0011 (10)	0.0052 (8)	0.0075 (8)
O22	0.0303 (9)	0.0278 (9)	0.0315 (9)	0.0001 (7)	0.0128 (7)	0.0094 (7)

Geometric parameters (Å, º)

I4—C14	2.099 (3)	C21—C22	1.392 (3)
C14—C13	1.385 (3)	C21—C26	1.392 (3)
C14—C13^i	1.385 (3)	C22—C23	1.383 (3)
C13—C12	1.391 (3)	C22—H22	0.9500
C13—H13	0.9500	C23—C24	1.384 (3)
C12—C11	1.387 (2)	C23—N2	1.475 (3)
C12—H12	0.9500	C24—C25	1.386 (3)
C11—C12^i	1.387 (2)	C24—H24	0.9500
C11—N1	1.451 (4)	C25—C26	1.385 (3)
N1—S1	1.6810 (11)	C25—H25	0.9500
N1—S1^i	1.6810 (11)	C26—H26	0.9500
S1—O11	1.4274 (14)	N2—O22	1.225 (3)
S1—O12	1.4279 (15)	N2—O21	1.229 (2)
S1—C21	1.761 (2)
C13—C14—C13^i	121.7 (3)	C22—C21—C26	121.80 (19)
C13—C14—I4	119.15 (13)	C22—C21—S1	119.48 (15)
C13^i—C14—I4	119.15 (13)	C26—C21—S1	118.70 (15)
C14—C13—C12	119.2 (2)	C23—C22—C21	116.66 (19)
C14—C13—H13	120.4	C23—C22—H22	121.7
C12—C13—H13	120.4	C21—C22—H22	121.7
C11—C12—C13	119.1 (2)	C22—C23—C24	123.27 (19)
C11—C12—H12	120.5	C22—C23—N2	118.13 (19)
C13—C12—H12	120.5	C24—C23—N2	118.59 (18)
C12^i—C11—C12	121.7 (3)	C23—C24—C25	118.5 (2)
C12^i—C11—N1	119.15 (13)	C23—C24—H24	120.7
C12—C11—N1	119.15 (13)	C25—C24—H24	120.7
C11—N1—S1	117.94 (7)	C26—C25—C24	120.4 (2)
C11—N1—S1^i	117.95 (7)	C26—C25—H25	119.8
S1—N1—S1^i	124.11 (14)	C24—C25—H25	119.8
O11—S1—O12	120.48 (9)	C25—C26—C21	119.4 (2)
O11—S1—N1	107.92 (9)	C25—C26—H26	120.3
O12—S1—N1	105.43 (9)	C21—C26—H26	120.3
O11—S1—C21	109.67 (9)	O22—N2—O21	124.37 (19)
O12—S1—C21	108.09 (9)	O22—N2—C23	118.34 (17)
N1—S1—C21	103.98 (6)	O21—N2—C23	117.3 (2)

Symmetry code: (i) −x, y, −z+3/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O12^ii	0.95	2.55	3.500 (2)	177

Symmetry code: (ii) −x, −y+1, −z+1.

(IV) N-(4'-Iodophenylsulfonyl)-3-nitroaniline

Crystal data

C12H9IN2O4S	Z = 2
Mr = 404.17	F(000) = 392
Triclinic, P1	Dx = 1.987 Mg m^−3
a = 7.6482 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.4274 (3) Å	Cell parameters from 3037 reflections
c = 10.8790 (3) Å	θ = 3.0–27.5°
α = 88.8029 (12)°	µ = 2.54 mm^−1
β = 75.8302 (12)°	T = 150 K
γ = 83.5777 (11)°	Plate, colourless
V = 675.58 (4) Å^3	0.20 × 0.20 × 0.10 mm

Data collection

Kappa-CCD diffractometer	3037 independent reflections
Radiation source: fine-focus sealed X-ray tube	2687 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.070
φ scans, and ω scans with κ offsets	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = −9→9
Tmin = 0.631, Tmax = 0.785	k = −10→10
10353 measured reflections	l = −13→14

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.080	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0415P)^2] where P = (Fo^2 + 2Fc^2)/3
3037 reflections	(Δ/σ)max = 0.001
181 parameters	Δρmax = 0.78 e Å^−3
0 restraints	Δρmin = −1.05 e Å^−3

Special details

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.27750 (10)	0.10143 (8)	0.17566 (7)	0.01817 (16)
O11	0.3322 (3)	−0.0602 (2)	0.13082 (19)	0.0226 (5)
O12	0.0900 (3)	0.1555 (2)	0.2265 (2)	0.0229 (5)
N1	0.3571 (3)	0.2100 (3)	0.0539 (2)	0.0209 (5)
C11	0.2991 (4)	0.3680 (3)	0.0245 (3)	0.0176 (6)
C12	0.1784 (4)	0.4730 (3)	0.1123 (3)	0.0178 (6)
C13	0.1276 (4)	0.6233 (3)	0.0699 (3)	0.0198 (6)
N2	−0.0049 (3)	0.7306 (3)	0.1592 (3)	0.0251 (6)
O21	−0.0485 (3)	0.6909 (3)	0.2712 (2)	0.0347 (6)
O22	−0.0688 (3)	0.8536 (3)	0.1178 (2)	0.0342 (6)
C14	0.1906 (4)	0.6751 (3)	−0.0520 (3)	0.0232 (6)
C15	0.3137 (4)	0.5689 (3)	−0.1371 (3)	0.0237 (6)
C16	0.3663 (4)	0.4182 (3)	−0.0983 (3)	0.0199 (6)
C21	0.3988 (4)	0.1360 (3)	0.2895 (3)	0.0192 (6)
C22	0.5732 (4)	0.0579 (3)	0.2748 (3)	0.0204 (6)
C23	0.6775 (4)	0.0921 (3)	0.3552 (3)	0.0220 (6)
C24	0.6043 (4)	0.2050 (3)	0.4523 (3)	0.0203 (6)
I1	0.77070 (3)	0.26547 (2)	0.567313 (17)	0.02795 (10)
C25	0.4291 (4)	0.2799 (4)	0.4690 (3)	0.0251 (7)
C26	0.3243 (4)	0.2443 (3)	0.3881 (3)	0.0228 (6)
H1	0.4506	0.1631	−0.0024	0.025*
H12	0.1331	0.4421	0.1976	0.021*
H14	0.1520	0.7790	−0.0776	0.028*
H15	0.3612	0.6009	−0.2218	0.028*
H16	0.4501	0.3474	−0.1568	0.024*
H22	0.6201	−0.0192	0.2091	0.025*
H23	0.7970	0.0402	0.3451	0.026*
H25	0.3811	0.3553	0.5357	0.030*
H26	0.2033	0.2931	0.3998	0.027*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0164 (4)	0.0189 (3)	0.0183 (4)	−0.0010 (3)	−0.0030 (3)	−0.0006 (3)
O11	0.0244 (11)	0.0203 (10)	0.0227 (11)	−0.0027 (9)	−0.0048 (9)	−0.0015 (8)
O12	0.0150 (10)	0.0271 (11)	0.0253 (11)	−0.0005 (8)	−0.0031 (9)	−0.0006 (9)
N1	0.0190 (13)	0.0225 (12)	0.0175 (12)	0.0024 (10)	0.0004 (10)	0.0009 (10)
C11	0.0143 (14)	0.0199 (13)	0.0201 (15)	−0.0033 (11)	−0.0067 (12)	0.0011 (11)
C12	0.0163 (14)	0.0227 (14)	0.0153 (14)	−0.0017 (11)	−0.0052 (11)	−0.0035 (11)
C13	0.0154 (14)	0.0211 (14)	0.0229 (15)	0.0004 (11)	−0.0052 (12)	−0.0071 (12)
N2	0.0192 (13)	0.0252 (13)	0.0327 (16)	−0.0016 (11)	−0.0094 (12)	−0.0096 (11)
O21	0.0320 (14)	0.0440 (14)	0.0251 (13)	0.0055 (11)	−0.0045 (11)	−0.0137 (11)
O22	0.0286 (13)	0.0245 (12)	0.0480 (15)	0.0096 (10)	−0.0113 (11)	−0.0077 (11)
C14	0.0220 (16)	0.0208 (14)	0.0293 (17)	−0.0041 (12)	−0.0101 (13)	0.0015 (12)
C15	0.0223 (16)	0.0261 (15)	0.0214 (15)	−0.0041 (12)	−0.0022 (13)	0.0016 (12)
C16	0.0181 (15)	0.0196 (14)	0.0202 (15)	−0.0022 (11)	−0.0008 (12)	−0.0053 (11)
C21	0.0185 (14)	0.0210 (14)	0.0170 (14)	−0.0040 (11)	−0.0017 (11)	0.0003 (11)
C22	0.0189 (15)	0.0183 (13)	0.0225 (15)	0.0008 (11)	−0.0030 (12)	−0.0026 (11)
C23	0.0172 (15)	0.0212 (14)	0.0256 (16)	0.0001 (12)	−0.0027 (12)	0.0020 (12)
C24	0.0224 (16)	0.0220 (14)	0.0188 (14)	−0.0067 (12)	−0.0076 (12)	0.0037 (12)
I1	0.02986 (15)	0.03481 (15)	0.02174 (14)	−0.00713 (10)	−0.00962 (10)	0.00067 (9)
C25	0.0274 (17)	0.0280 (15)	0.0173 (15)	−0.0012 (13)	−0.0011 (13)	−0.0041 (12)
C26	0.0200 (16)	0.0254 (15)	0.0207 (15)	0.0029 (12)	−0.0033 (12)	0.0006 (12)

Geometric parameters (Å, º)

S1—O12	1.431 (2)	C14—H14	0.9500
S1—O11	1.438 (2)	C15—C16	1.379 (4)
S1—N1	1.626 (3)	C15—H15	0.9500
S1—C21	1.766 (3)	C16—H16	0.9500
N1—C11	1.411 (4)	C21—C26	1.390 (4)
N1—H1	0.8800	C21—C22	1.393 (4)
C11—C16	1.384 (4)	C22—C23	1.373 (4)
C11—C12	1.403 (4)	C22—H22	0.9500
C12—C13	1.386 (4)	C23—C24	1.403 (4)
C12—H12	0.9500	C23—H23	0.9500
C13—C14	1.375 (4)	C24—C25	1.387 (4)
C13—N2	1.462 (4)	C24—I1	2.097 (3)
N2—O22	1.221 (3)	C25—C26	1.384 (4)
N2—O21	1.231 (4)	C25—H25	0.9500
C14—C15	1.401 (4)	C26—H26	0.9500
O12—S1—O11	120.49 (13)	C16—C15—C14	120.3 (3)
O12—S1—N1	109.04 (13)	C16—C15—H15	119.9
O11—S1—N1	104.24 (13)	C14—C15—H15	119.9
O12—S1—C21	108.61 (13)	C15—C16—C11	121.2 (3)
O11—S1—C21	107.47 (13)	C15—C16—H16	119.4
N1—S1—C21	106.09 (13)	C11—C16—H16	119.4
C11—N1—S1	129.9 (2)	C26—C21—C22	121.1 (3)
C11—N1—H1	115.1	C26—C21—S1	120.4 (2)
S1—N1—H1	115.1	C22—C21—S1	118.5 (2)
C16—C11—C12	119.8 (3)	C23—C22—C21	120.1 (3)
C16—C11—N1	116.9 (2)	C23—C22—H22	120.0
C12—C11—N1	123.4 (3)	C21—C22—H22	120.0
C13—C12—C11	117.5 (3)	C22—C23—C24	118.8 (3)
C13—C12—H12	121.2	C22—C23—H23	120.6
C11—C12—H12	121.2	C24—C23—H23	120.6
C14—C13—C12	123.8 (3)	C25—C24—C23	121.1 (3)
C14—C13—N2	118.3 (3)	C25—C24—I1	120.6 (2)
C12—C13—N2	117.9 (3)	C23—C24—I1	118.3 (2)
O22—N2—O21	123.6 (3)	C26—C25—C24	119.8 (3)
O22—N2—C13	117.9 (3)	C26—C25—H25	120.1
O21—N2—C13	118.5 (2)	C24—C25—H25	120.1
C13—C14—C15	117.5 (3)	C25—C26—C21	119.1 (3)
C13—C14—H14	121.3	C25—C26—H26	120.5
C15—C14—H14	121.3	C21—C26—H26	120.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O11^i	0.88	2.01	2.894 (3)	179
C22—H22···O22^ii	0.95	2.47	3.187 (4)	132

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

(V) N-(4'-Iodophenylsulfonyl)-4-methyl-2-nitroaniline

Crystal data

C13H11IN2O4S	Z = 2
Mr = 418.20	F(000) = 408
Triclinic, P1	Dx = 1.912 Mg m^−3
a = 5.4333 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.9336 (5) Å	Cell parameters from 3174 reflections
c = 12.5713 (7) Å	θ = 1.6–27.4°
α = 95.5668 (18)°	µ = 2.36 mm^−1
β = 93.0809 (17)°	T = 150 K
γ = 101.4226 (17)°	Plate, colourless
V = 726.52 (6) Å^3	0.15 × 0.10 × 0.04 mm

Data collection

Kappa-CCD diffractometer	3174 independent reflections
Radiation source: fine-focus sealed X-ray tube	2802 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.055
φ scans, and ω scans with κ offsets	θmax = 27.4°, θmin = 1.6°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = −7→7
Tmin = 0.718, Tmax = 0.911	k = −13→13
9313 measured reflections	l = −16→16

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.082	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0314P)^2 + 0.8392P] where P = (Fo^2 + 2Fc^2)/3
3174 reflections	(Δ/σ)max = 0.001
191 parameters	Δρmax = 0.71 e Å^−3
0 restraints	Δρmin = −1.02 e Å^−3

Special details

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	−0.13829 (14)	0.08208 (7)	−0.14650 (6)	0.02314 (16)
O11	−0.3000 (4)	0.1451 (2)	−0.20449 (18)	0.0305 (5)
O12	−0.2356 (4)	0.0114 (2)	−0.06257 (17)	0.0299 (5)
N1	0.1039 (5)	0.1837 (2)	−0.08796 (19)	0.0246 (5)
C11	0.2583 (6)	0.2804 (3)	−0.1337 (2)	0.0217 (6)
C12	0.4890 (6)	0.3475 (3)	−0.0818 (2)	0.0223 (6)
N2	0.5808 (5)	0.3208 (2)	0.0231 (2)	0.0278 (6)
O21	0.7976 (5)	0.3682 (3)	0.0565 (2)	0.0457 (7)
O22	0.4377 (5)	0.2522 (2)	0.07556 (18)	0.0384 (6)
C13	0.6461 (6)	0.4403 (3)	−0.1286 (2)	0.0257 (6)
C14	0.5801 (6)	0.4736 (3)	−0.2280 (2)	0.0266 (6)
C17	0.7501 (7)	0.5743 (3)	−0.2778 (3)	0.0327 (7)
C15	0.3506 (6)	0.4090 (3)	−0.2792 (2)	0.0277 (7)
C16	0.1926 (6)	0.3151 (3)	−0.2340 (2)	0.0260 (6)
C21	−0.0198 (5)	−0.0176 (3)	−0.2413 (2)	0.0205 (6)
C22	0.1676 (6)	−0.0801 (3)	−0.2080 (2)	0.0240 (6)
C23	0.2508 (6)	−0.1611 (3)	−0.2824 (2)	0.0250 (6)
C24	0.1465 (6)	−0.1787 (3)	−0.3876 (2)	0.0236 (6)
I1	0.27317 (4)	−0.30021 (2)	−0.502453 (16)	0.03746 (10)
C25	−0.0390 (6)	−0.1179 (3)	−0.4204 (2)	0.0267 (6)
C26	−0.1238 (6)	−0.0358 (3)	−0.3459 (2)	0.0256 (6)
H1	0.1419	0.1771	−0.0201	0.029*
H13	0.8019	0.4816	−0.0916	0.031*
H17A	0.7429	0.6566	−0.2410	0.049*
H17B	0.6952	0.5709	−0.3538	0.049*
H17C	0.9233	0.5612	−0.2711	0.049*
H15	0.3004	0.4299	−0.3476	0.033*
H16	0.0376	0.2738	−0.2717	0.031*
H22	0.2361	−0.0670	−0.1357	0.029*
H23	0.3781	−0.2043	−0.2620	0.030*
H25	−0.1080	−0.1318	−0.4927	0.032*
H26	−0.2514	0.0072	−0.3667	0.031*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0221 (4)	0.0224 (4)	0.0233 (3)	0.0023 (3)	0.0027 (3)	−0.0016 (3)
O11	0.0254 (12)	0.0287 (12)	0.0371 (12)	0.0083 (9)	−0.0019 (9)	−0.0014 (9)
O12	0.0286 (12)	0.0332 (13)	0.0253 (11)	−0.0009 (9)	0.0085 (9)	0.0015 (9)
N1	0.0278 (13)	0.0235 (13)	0.0189 (12)	−0.0010 (10)	−0.0006 (10)	−0.0007 (9)
C11	0.0231 (14)	0.0186 (14)	0.0228 (14)	0.0050 (11)	0.0022 (11)	−0.0028 (10)
C12	0.0276 (16)	0.0197 (15)	0.0198 (13)	0.0082 (11)	−0.0014 (11)	−0.0020 (10)
N2	0.0330 (15)	0.0214 (14)	0.0263 (13)	0.0035 (11)	−0.0052 (11)	−0.0022 (10)
O21	0.0337 (14)	0.0547 (18)	0.0417 (14)	−0.0059 (12)	−0.0164 (11)	0.0111 (12)
O22	0.0471 (15)	0.0347 (14)	0.0266 (12)	−0.0060 (11)	−0.0082 (10)	0.0059 (10)
C13	0.0253 (16)	0.0235 (16)	0.0264 (15)	0.0035 (12)	−0.0021 (12)	−0.0017 (11)
C14	0.0280 (16)	0.0241 (16)	0.0280 (15)	0.0065 (12)	0.0033 (12)	0.0004 (12)
C17	0.0335 (18)	0.0285 (18)	0.0344 (17)	0.0016 (14)	0.0040 (14)	0.0040 (13)
C15	0.0319 (17)	0.0274 (17)	0.0240 (15)	0.0073 (13)	0.0015 (12)	0.0020 (12)
C16	0.0265 (16)	0.0260 (16)	0.0235 (15)	0.0028 (12)	−0.0025 (12)	0.0000 (11)
C21	0.0215 (14)	0.0175 (14)	0.0208 (13)	0.0005 (11)	0.0018 (11)	0.0010 (10)
C22	0.0261 (15)	0.0272 (16)	0.0180 (13)	0.0041 (12)	−0.0008 (11)	0.0021 (11)
C23	0.0267 (16)	0.0260 (16)	0.0226 (14)	0.0076 (12)	−0.0007 (12)	0.0005 (11)
C24	0.0266 (15)	0.0239 (16)	0.0191 (13)	0.0032 (12)	0.0016 (11)	0.0007 (11)
I1	0.04258 (16)	0.04400 (17)	0.02540 (13)	0.01622 (11)	−0.00247 (9)	−0.01065 (9)
C25	0.0318 (17)	0.0291 (17)	0.0180 (14)	0.0042 (13)	−0.0015 (12)	0.0031 (11)
C26	0.0288 (16)	0.0252 (16)	0.0236 (14)	0.0071 (12)	−0.0014 (12)	0.0049 (11)

Geometric parameters (Å, º)

S1—O12	1.431 (2)	C17—H17B	0.9800
S1—O11	1.431 (2)	C17—H17C	0.9800
S1—N1	1.633 (3)	C15—C16	1.390 (4)
S1—C21	1.769 (3)	C15—H15	0.9500
N1—C11	1.404 (4)	C16—H16	0.9500
N1—H1	0.8800	C21—C26	1.383 (4)
C11—C16	1.400 (4)	C21—C22	1.402 (4)
C11—C12	1.411 (4)	C22—C23	1.381 (4)
C12—C13	1.389 (4)	C22—H22	0.9500
C12—N2	1.462 (4)	C23—C24	1.390 (4)
N2—O21	1.222 (4)	C23—H23	0.9500
N2—O22	1.234 (4)	C24—C25	1.380 (4)
C13—C14	1.385 (4)	C24—I1	2.102 (3)
C13—H13	0.9500	C25—C26	1.394 (4)
C14—C15	1.395 (4)	C25—H25	0.9500
C14—C17	1.500 (4)	C26—H26	0.9500
C17—H17A	0.9800
O12—S1—O11	119.11 (14)	C14—C17—H17C	109.5
O12—S1—N1	104.18 (13)	H17A—C17—H17C	109.5
O11—S1—N1	109.97 (14)	H17B—C17—H17C	109.5
O12—S1—C21	108.90 (14)	C16—C15—C14	122.4 (3)
O11—S1—C21	107.32 (13)	C16—C15—H15	118.8
N1—S1—C21	106.77 (14)	C14—C15—H15	118.8
C11—N1—S1	127.3 (2)	C15—C16—C11	121.0 (3)
C11—N1—H1	116.3	C15—C16—H16	119.5
S1—N1—H1	116.3	C11—C16—H16	119.5
C16—C11—N1	121.8 (3)	C26—C21—C22	121.8 (3)
C16—C11—C12	116.1 (3)	C26—C21—S1	118.6 (2)
N1—C11—C12	122.1 (3)	C22—C21—S1	119.6 (2)
C13—C12—C11	122.2 (3)	C23—C22—C21	118.7 (3)
C13—C12—N2	115.9 (3)	C23—C22—H22	120.7
C11—C12—N2	121.9 (3)	C21—C22—H22	120.7
O21—N2—O22	122.0 (3)	C22—C23—C24	119.4 (3)
O21—N2—C12	118.7 (3)	C22—C23—H23	120.3
O22—N2—C12	119.3 (3)	C24—C23—H23	120.3
C14—C13—C12	121.3 (3)	C25—C24—C23	122.0 (3)
C14—C13—H13	119.4	C25—C24—I1	118.0 (2)
C12—C13—H13	119.4	C23—C24—I1	120.0 (2)
C13—C14—C15	116.9 (3)	C24—C25—C26	118.9 (3)
C13—C14—C17	121.0 (3)	C24—C25—H25	120.5
C15—C14—C17	122.1 (3)	C26—C25—H25	120.5
C14—C17—H17A	109.5	C21—C26—C25	119.2 (3)
C14—C17—H17B	109.5	C21—C26—H26	120.4
H17A—C17—H17B	109.5	C25—C26—H26	120.4

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O22	0.88	1.94	2.615 (3)	132
N1—H1···O12^i	0.88	2.52	3.144 (3)	128
C13—H13···O21^ii	0.95	2.44	3.342 (4)	158

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

(VI) N-(4'-Iodophenylsulfonyl)-2-nitroaniline

Crystal data

C12H9IN2O4S	Z = 4
Mr = 404.17	F(000) = 784
Triclinic, P1	Dx = 1.989 Mg m^−3
a = 8.1228 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.0723 (2) Å	Cell parameters from 5161 reflections
c = 14.4738 (3) Å	θ = 3.1–26.0°
α = 113.4712 (11)°	µ = 2.54 mm^−1
β = 100.7181 (9)°	T = 150 K
γ = 97.3706 (10)°	Plate, colourless
V = 1349.76 (5) Å^3	0.20 × 0.15 × 0.10 mm

Data collection

Kappa-CCD diffractometer	5161 independent reflections
Radiation source: fine-focus sealed X-ray tube	4442 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.092
φ scans, and ω scans with κ offsets	θmax = 26.0°, θmin = 3.1°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = −10→9
Tmin = 0.630, Tmax = 0.785	k = −16→16
13324 measured reflections	l = −17→17

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.120	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0722P)^2] where P = (Fo^2 + 2Fc^2)/3
5161 reflections	(Δ/σ)max = 0.001
361 parameters	Δρmax = 1.10 e Å^−3
0 restraints	Δρmin = −2.49 e Å^−3

Special details

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.84857 (13)	0.44387 (9)	0.24485 (8)	0.0226 (2)
O11	0.8201 (4)	0.3253 (2)	0.1747 (2)	0.0287 (7)
O12	1.0105 (4)	0.5187 (3)	0.2675 (2)	0.0303 (7)
N1	0.8150 (4)	0.4423 (3)	0.3524 (2)	0.0229 (7)
C11	0.8160 (5)	0.5373 (3)	0.4423 (3)	0.0191 (8)
C12	0.7590 (5)	0.5267 (3)	0.5252 (3)	0.0224 (8)
N2	0.6923 (4)	0.4150 (3)	0.5200 (3)	0.0255 (8)
O21	0.7378 (4)	0.3304 (2)	0.4626 (2)	0.0311 (7)
O22	0.5953 (4)	0.4094 (3)	0.5747 (2)	0.0366 (8)
C13	0.7644 (6)	0.6212 (4)	0.6156 (3)	0.0288 (9)
C14	0.8239 (6)	0.7295 (4)	0.6267 (3)	0.0324 (10)
C15	0.8745 (6)	0.7427 (3)	0.5453 (3)	0.0291 (10)
C16	0.8715 (5)	0.6498 (3)	0.4549 (3)	0.0265 (9)
C21	0.6847 (5)	0.5040 (3)	0.2024 (3)	0.0233 (9)
C22	0.5172 (5)	0.4667 (3)	0.2037 (3)	0.0243 (9)
C23	0.3879 (6)	0.5125 (3)	0.1709 (3)	0.0267 (9)
C24	0.4255 (6)	0.5921 (3)	0.1326 (3)	0.0251 (9)
I1	0.22489 (4)	0.65677 (2)	0.07762 (2)	0.03109 (13)
C25	0.5917 (6)	0.6297 (4)	0.1316 (3)	0.0311 (10)
C26	0.7233 (6)	0.5861 (3)	0.1662 (3)	0.0297 (10)
S2	0.45171 (13)	0.10296 (8)	0.22612 (8)	0.0208 (2)
O31	0.5202 (4)	0.2203 (2)	0.2508 (2)	0.0261 (6)
O32	0.2746 (4)	0.0516 (2)	0.1746 (2)	0.0267 (6)
N3	0.4919 (4)	0.0963 (3)	0.3391 (2)	0.0239 (7)
C31	0.4299 (5)	−0.0059 (3)	0.3476 (3)	0.0229 (9)
C32	0.5372 (5)	−0.0731 (3)	0.3702 (3)	0.0253 (9)
N4	0.7211 (5)	−0.0467 (3)	0.3836 (3)	0.0352 (9)
O41	0.7971 (5)	−0.1236 (3)	0.3745 (4)	0.0686 (13)
O42	0.7951 (4)	0.0507 (3)	0.4049 (3)	0.0418 (8)
C33	0.4697 (6)	−0.1714 (4)	0.3809 (3)	0.0305 (10)
C34	0.2964 (6)	−0.2017 (4)	0.3684 (3)	0.0323 (10)
C35	0.1892 (6)	−0.1363 (4)	0.3449 (3)	0.0292 (9)
C36	0.2558 (5)	−0.0395 (3)	0.3347 (3)	0.0251 (9)
C41	0.5742 (5)	0.0174 (3)	0.1514 (3)	0.0192 (8)
C42	0.7514 (6)	0.0570 (4)	0.1783 (3)	0.0288 (10)
C43	0.8486 (5)	−0.0102 (4)	0.1222 (3)	0.0280 (9)
C44	0.7654 (5)	−0.1162 (3)	0.0375 (3)	0.0212 (8)
I2	0.91695 (4)	−0.21363 (2)	−0.04833 (2)	0.02809 (12)
C45	0.5891 (5)	−0.1534 (3)	0.0099 (3)	0.0253 (9)
C46	0.4919 (5)	−0.0866 (3)	0.0682 (3)	0.0236 (8)
H1	0.7944	0.3751	0.3536	0.028*
H13	0.7266	0.6109	0.6703	0.035*
H14	0.8303	0.7944	0.6893	0.039*
H15	0.9122	0.8177	0.5518	0.035*
H16	0.9074	0.6618	0.4005	0.032*
H22	0.4923	0.4097	0.2273	0.029*
H23	0.2742	0.4899	0.1745	0.032*
H25	0.6156	0.6860	0.1070	0.037*
H26	0.8377	0.6114	0.1653	0.036*
H3	0.5528	0.1571	0.3955	0.029*
H33	0.5437	−0.2162	0.3968	0.037*
H34	0.2497	−0.2677	0.3757	0.039*
H35	0.0690	−0.1580	0.3357	0.035*
H36	0.1805	0.0045	0.3186	0.030*
H42	0.8051	0.1296	0.2348	0.035*
H43	0.9701	0.0148	0.1405	0.034*
H45	0.5343	−0.2242	−0.0486	0.030*
H46	0.3706	−0.1120	0.0509	0.028*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0253 (5)	0.0230 (5)	0.0250 (5)	0.0099 (4)	0.0117 (4)	0.0125 (4)
O11	0.0391 (18)	0.0252 (15)	0.0271 (15)	0.0164 (13)	0.0168 (13)	0.0104 (13)
O12	0.0228 (16)	0.0361 (17)	0.0404 (17)	0.0075 (13)	0.0130 (14)	0.0226 (15)
N1	0.0304 (19)	0.0177 (16)	0.0230 (17)	0.0081 (15)	0.0094 (15)	0.0091 (14)
C11	0.0169 (19)	0.0189 (18)	0.0227 (19)	0.0066 (15)	0.0043 (16)	0.0099 (16)
C12	0.019 (2)	0.023 (2)	0.025 (2)	0.0049 (16)	0.0027 (16)	0.0119 (17)
N2	0.0258 (19)	0.0278 (19)	0.0262 (18)	0.0052 (15)	0.0049 (15)	0.0160 (16)
O21	0.0427 (19)	0.0214 (15)	0.0290 (15)	0.0056 (13)	0.0092 (14)	0.0112 (13)
O22	0.0343 (18)	0.0440 (19)	0.0441 (19)	0.0101 (15)	0.0205 (16)	0.0267 (16)
C13	0.029 (2)	0.031 (2)	0.026 (2)	0.0101 (19)	0.0080 (18)	0.0106 (19)
C14	0.030 (2)	0.025 (2)	0.029 (2)	0.0098 (19)	0.0057 (19)	−0.0006 (19)
C15	0.028 (2)	0.019 (2)	0.036 (2)	0.0053 (18)	0.0068 (19)	0.0088 (19)
C16	0.026 (2)	0.024 (2)	0.029 (2)	0.0012 (18)	0.0076 (18)	0.0112 (18)
C21	0.027 (2)	0.023 (2)	0.0226 (19)	0.0084 (17)	0.0079 (17)	0.0112 (17)
C22	0.025 (2)	0.022 (2)	0.030 (2)	0.0039 (17)	0.0112 (18)	0.0149 (18)
C23	0.028 (2)	0.024 (2)	0.034 (2)	0.0084 (18)	0.0127 (19)	0.0160 (19)
C24	0.028 (2)	0.024 (2)	0.023 (2)	0.0101 (18)	0.0076 (17)	0.0081 (17)
I1	0.0344 (2)	0.03262 (19)	0.03155 (19)	0.01418 (14)	0.00807 (14)	0.01735 (15)
C25	0.035 (3)	0.031 (2)	0.037 (2)	0.010 (2)	0.009 (2)	0.024 (2)
C26	0.030 (2)	0.026 (2)	0.038 (2)	0.0019 (18)	0.015 (2)	0.018 (2)
S2	0.0218 (5)	0.0180 (5)	0.0257 (5)	0.0064 (4)	0.0084 (4)	0.0109 (4)
O31	0.0333 (17)	0.0179 (13)	0.0318 (15)	0.0056 (12)	0.0124 (13)	0.0137 (12)
O32	0.0217 (15)	0.0242 (14)	0.0330 (16)	0.0067 (12)	0.0058 (13)	0.0112 (13)
N3	0.0311 (19)	0.0130 (15)	0.0248 (17)	0.0017 (14)	0.0082 (15)	0.0060 (14)
C31	0.032 (2)	0.0164 (18)	0.0199 (19)	0.0062 (17)	0.0084 (17)	0.0061 (16)
C32	0.027 (2)	0.026 (2)	0.023 (2)	0.0060 (18)	0.0074 (17)	0.0104 (17)
N4	0.028 (2)	0.041 (2)	0.043 (2)	0.0102 (18)	0.0086 (18)	0.024 (2)
O41	0.037 (2)	0.058 (2)	0.125 (4)	0.0278 (19)	0.030 (2)	0.044 (3)
O42	0.0268 (17)	0.048 (2)	0.053 (2)	0.0004 (15)	0.0056 (16)	0.0297 (18)
C33	0.036 (3)	0.030 (2)	0.030 (2)	0.010 (2)	0.0079 (19)	0.0170 (19)
C34	0.039 (3)	0.026 (2)	0.036 (2)	0.0016 (19)	0.008 (2)	0.021 (2)
C35	0.022 (2)	0.032 (2)	0.040 (2)	0.0039 (18)	0.0139 (19)	0.019 (2)
C36	0.027 (2)	0.024 (2)	0.032 (2)	0.0107 (17)	0.0135 (18)	0.0157 (18)
C41	0.019 (2)	0.0196 (19)	0.0216 (19)	0.0072 (16)	0.0074 (16)	0.0097 (16)
C42	0.024 (2)	0.022 (2)	0.032 (2)	−0.0011 (17)	0.0056 (18)	0.0071 (18)
C43	0.019 (2)	0.029 (2)	0.034 (2)	0.0043 (17)	0.0073 (18)	0.0118 (19)
C44	0.026 (2)	0.0194 (19)	0.0242 (19)	0.0089 (16)	0.0107 (17)	0.0126 (17)
I2	0.0282 (2)	0.02805 (18)	0.03217 (19)	0.01372 (13)	0.01172 (13)	0.01323 (14)
C45	0.026 (2)	0.023 (2)	0.027 (2)	0.0063 (17)	0.0070 (18)	0.0101 (18)
C46	0.019 (2)	0.023 (2)	0.029 (2)	0.0033 (16)	0.0069 (17)	0.0107 (18)

Geometric parameters (Å, º)

S1—O12	1.431 (3)	S2—O32	1.425 (3)
S1—O11	1.433 (3)	S2—O31	1.436 (3)
S1—N1	1.638 (3)	S2—N3	1.646 (3)
S1—C21	1.765 (4)	S2—C41	1.770 (4)
N1—C11	1.393 (5)	N3—C31	1.426 (5)
N1—H1	0.8800	N3—H3	0.8800
C11—C16	1.409 (5)	C31—C36	1.381 (6)
C11—C12	1.413 (5)	C31—C32	1.399 (6)
C12—C13	1.385 (6)	C32—C33	1.409 (6)
C12—N2	1.458 (5)	C32—N4	1.448 (5)
N2—O22	1.232 (5)	N4—O41	1.222 (5)
N2—O21	1.239 (4)	N4—O42	1.224 (5)
C13—C14	1.371 (6)	C33—C34	1.370 (6)
C13—H13	0.9500	C33—H33	0.9500
C14—C15	1.382 (6)	C34—C35	1.385 (6)
C14—H14	0.9500	C34—H34	0.9500
C15—C16	1.380 (6)	C35—C36	1.385 (6)
C15—H15	0.9500	C35—H35	0.9500
C16—H16	0.9500	C36—H36	0.9500
C21—C22	1.391 (6)	C41—C46	1.381 (5)
C21—C26	1.396 (5)	C41—C42	1.390 (6)
C22—C23	1.374 (6)	C42—C43	1.379 (6)
C22—H22	0.9500	C42—H42	0.9500
C23—C24	1.388 (6)	C43—C44	1.406 (6)
C23—H23	0.9500	C43—H43	0.9500
C24—C25	1.381 (6)	C44—C45	1.379 (6)
C24—I1	2.099 (4)	C44—I2	2.096 (4)
C25—C26	1.379 (6)	C45—C46	1.391 (5)
C25—H25	0.9500	C45—H45	0.9500
C26—H26	0.9500	C46—H46	0.9500
O12—S1—O11	119.28 (18)	O32—S2—O31	120.61 (18)
O12—S1—N1	109.93 (18)	O32—S2—N3	107.96 (18)
O11—S1—N1	104.09 (17)	O31—S2—N3	104.81 (17)
O12—S1—C21	108.00 (18)	O32—S2—C41	107.73 (18)
O11—S1—C21	110.03 (19)	O31—S2—C41	108.33 (17)
N1—S1—C21	104.53 (18)	N3—S2—C41	106.63 (17)
C11—N1—S1	126.1 (3)	C31—N3—S2	121.4 (3)
C11—N1—H1	117.0	C31—N3—H3	119.3
S1—N1—H1	117.0	S2—N3—H3	119.3
N1—C11—C16	121.8 (4)	C36—C31—C32	118.1 (4)
N1—C11—C12	122.1 (4)	C36—C31—N3	118.6 (4)
C16—C11—C12	116.1 (3)	C32—C31—N3	123.3 (4)
C13—C12—C11	122.1 (4)	C31—C32—C33	121.0 (4)
C13—C12—N2	116.5 (3)	C31—C32—N4	122.6 (4)
C11—C12—N2	121.4 (3)	C33—C32—N4	116.4 (4)
O22—N2—O21	122.9 (3)	O41—N4—O42	122.5 (4)
O22—N2—C12	118.2 (3)	O41—N4—C32	117.8 (4)
O21—N2—C12	118.9 (3)	O42—N4—C32	119.7 (4)
C14—C13—C12	120.3 (4)	C34—C33—C32	119.4 (4)
C14—C13—H13	119.8	C34—C33—H33	120.3
C12—C13—H13	119.8	C32—C33—H33	120.3
C13—C14—C15	119.0 (4)	C33—C34—C35	120.0 (4)
C13—C14—H14	120.5	C33—C34—H34	120.0
C15—C14—H14	120.5	C35—C34—H34	120.0
C16—C15—C14	121.6 (4)	C34—C35—C36	120.6 (4)
C16—C15—H15	119.2	C34—C35—H35	119.7
C14—C15—H15	119.2	C36—C35—H35	119.7
C15—C16—C11	120.8 (4)	C31—C36—C35	121.0 (4)
C15—C16—H16	119.6	C31—C36—H36	119.5
C11—C16—H16	119.6	C35—C36—H36	119.5
C22—C21—C26	120.8 (4)	C46—C41—C42	121.7 (4)
C22—C21—S1	119.1 (3)	C46—C41—S2	119.4 (3)
C26—C21—S1	120.0 (3)	C42—C41—S2	118.8 (3)
C23—C22—C21	120.0 (4)	C43—C42—C41	119.3 (4)
C23—C22—H22	120.0	C43—C42—H42	120.3
C21—C22—H22	120.0	C41—C42—H42	120.3
C22—C23—C24	119.2 (4)	C42—C43—C44	119.1 (4)
C22—C23—H23	120.4	C42—C43—H43	120.4
C24—C23—H23	120.4	C44—C43—H43	120.4
C25—C24—C23	121.0 (4)	C45—C44—C43	121.0 (4)
C25—C24—I1	120.3 (3)	C45—C44—I2	121.0 (3)
C23—C24—I1	118.8 (3)	C43—C44—I2	118.0 (3)
C26—C25—C24	120.4 (4)	C44—C45—C46	119.6 (4)
C26—C25—H25	119.8	C44—C45—H45	120.2
C24—C25—H25	119.8	C46—C45—H45	120.2
C25—C26—C21	118.6 (4)	C41—C46—C45	119.1 (4)
C25—C26—H26	120.7	C41—C46—H46	120.5
C21—C26—H26	120.7	C45—C46—H46	120.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O21	0.88	1.99	2.659 (5)	131
N3—H3···O21	0.88	2.27	3.049 (5)	147
C35—H35···O41^i	0.95	2.43	3.308 (7)	153
C43—H43···O32^ii	0.95	2.38	3.320 (5)	172

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