2-(4,5-Dimeth-oxy-2-nitro-phen-yl)-4-meth-oxy-3-methyl-9-phenyl-sulfonyl-9H-carbazole.

In the title compound, C28H24N2O7S, the carbazole system is essentially planar, with a maximum deviation of 0.0644 (19) Å for the C atom connected to the 4,5-dimeth-oxy-2-nitro-phenyl group. The dihedral angle between the carbazole moiety and the dimethoxy-substituted nitrophenyl ring is 58.55 (7)°. The sulfonyl group forms two intra-molecular C-H⋯O bonds with the adjacent carbazole system, forming two cyclic S(6) motifs. In the crystal, mol-ecules are linked along the a axis in bands consisting of cyclic R 3 (3)(15) motifs through two further C-H⋯O hydrogen bonds.

Related literature

For the biological activity and uses of carbazole derivatives, see: Itoigawa et al. (2000 ▶); Ramsewak et al. (1999 ▶). For their electronic properties and applications, see: Friend et al. (1999 ▶); Zhang et al. (2004 ▶). For related structures, see: Gopinath et al. (2013 ▶); Narayanan et al. (2014a ▶,b ▶). For the Thorpe–Ingold effect, see: Bassindale et al. (1984 ▶). For bond-length distortions, see: Allen et al. (1987 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C28H24N2O7S

M = 532.56

Orthorhombic,

a = 8.4543 (3) Å

b = 13.6605 (5) Å

c = 21.6359 (9) Å

V = 2498.73 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.18 mm−1

T = 296 K

0.25 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.956, T max = 0.964

14161 measured reflections

5152 independent reflections

4175 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.085

S = 1.00

5152 reflections

347 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814003535/ld2120sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814003535/ld2120Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814003535/ld2120Isup3.cml

CCDC reference: 987381

Additional supporting information: crystallographic information; 3D view; checkCIF report

C28H24N2O7S	F(000) = 1112
Mr = 532.56	Dx = 1.416 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 4175 reflections
a = 8.4543 (3) Å	θ = 2.4–27.2°
b = 13.6605 (5) Å	µ = 0.18 mm−1
c = 21.6359 (9) Å	T = 296 K
V = 2498.73 (16) Å3	Block, colourless
Z = 4	0.25 × 0.25 × 0.20 mm

Bruker Kappa APEXII CCD diffractometer	5152 independent reflections
Radiation source: fine-focus sealed tube	4175 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
ω and φ scans	θmax = 27.2°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −10→10
Tmin = 0.956, Tmax = 0.964	k = −10→17
14161 measured reflections	l = −27→27

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.085	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0466P)2 + 0.0209P] where P = (Fo2 + 2Fc2)/3
5152 reflections	(Δ/σ)max < 0.001
347 parameters	Δρmax = 0.15 e Å−3
1 restraint	Δρmin = −0.20 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
C1	0.1268 (2)	0.39477 (15)	0.48958 (10)	0.0410 (5)
C2	0.0620 (3)	0.41019 (19)	0.43157 (11)	0.0551 (6)
H2	0.0564	0.3601	0.4026	0.066*
C3	0.0063 (3)	0.5026 (2)	0.41856 (12)	0.0605 (7)
H3	−0.0398	0.5146	0.3803	0.073*
C4	0.0172 (3)	0.57813 (19)	0.46105 (12)	0.0550 (6)
H4	−0.0196	0.6401	0.4505	0.066*
C5	0.0817 (2)	0.56294 (17)	0.51863 (11)	0.0464 (5)
H5	0.0879	0.6137	0.5472	0.056*
C6	0.1375 (2)	0.46967 (16)	0.53321 (9)	0.0368 (5)
C7	0.2083 (2)	0.42888 (14)	0.58853 (9)	0.0335 (4)
C8	0.2422 (2)	0.46675 (13)	0.64640 (10)	0.0340 (4)
C9	0.2998 (2)	0.40758 (15)	0.69354 (9)	0.0377 (5)
C10	0.3300 (2)	0.30846 (14)	0.68049 (9)	0.0348 (4)
C11	0.3021 (2)	0.26937 (15)	0.62219 (9)	0.0363 (4)
H11	0.3258	0.2043	0.6136	0.044*
C12	0.2382 (2)	0.32938 (14)	0.57735 (9)	0.0340 (4)
C13	0.3936 (2)	0.24103 (14)	0.72890 (9)	0.0352 (4)
C14	0.5425 (2)	0.25771 (15)	0.75502 (9)	0.0383 (5)
H14	0.5989	0.3134	0.7438	0.046*
C15	0.6080 (2)	0.19307 (14)	0.79735 (10)	0.0372 (4)
C16	0.5267 (2)	0.10765 (14)	0.81391 (9)	0.0356 (4)
C17	0.3815 (2)	0.08873 (15)	0.78787 (10)	0.0380 (4)
H17	0.3271	0.0316	0.7976	0.046*
C18	0.3174 (2)	0.15556 (15)	0.74717 (9)	0.0365 (4)
C19	−0.0262 (2)	0.16388 (16)	0.51846 (11)	0.0460 (5)
C20	−0.1607 (3)	0.18574 (18)	0.48542 (16)	0.0630 (7)
H20	−0.1538	0.2158	0.4470	0.076*
C21	−0.3066 (3)	0.1621 (2)	0.51058 (19)	0.0755 (9)
H21	−0.3986	0.1764	0.4889	0.091*
C22	−0.3159 (3)	0.1178 (2)	0.5671 (2)	0.0778 (9)
H22	−0.4144	0.1019	0.5834	0.093*
C23	−0.1818 (3)	0.0967 (2)	0.59984 (16)	0.0728 (8)
H23	−0.1896	0.0675	0.6385	0.087*
C24	−0.0346 (3)	0.11877 (18)	0.57567 (13)	0.0558 (6)
H24	0.0570	0.1036	0.5974	0.067*
C25	0.3301 (3)	0.63070 (16)	0.63949 (13)	0.0551 (6)
H25A	0.4234	0.6198	0.6638	0.083*
H25B	0.2946	0.6969	0.6451	0.083*
H25C	0.3539	0.6198	0.5967	0.083*
C26	0.3229 (3)	0.44965 (18)	0.75693 (11)	0.0550 (6)
H26A	0.4304	0.4713	0.7614	0.082*
H26B	0.3004	0.4005	0.7874	0.082*
H26C	0.2528	0.5042	0.7626	0.082*
C27	0.8274 (3)	0.29669 (17)	0.81872 (13)	0.0578 (7)
H27A	0.8500	0.3075	0.7758	0.087*
H27B	0.9244	0.2960	0.8417	0.087*
H27C	0.7607	0.3483	0.8338	0.087*
C28	0.5132 (3)	−0.03112 (18)	0.87996 (12)	0.0595 (7)
H28A	0.4161	−0.0079	0.8976	0.089*
H28B	0.5748	−0.0632	0.9113	0.089*
H28C	0.4903	−0.0766	0.8473	0.089*
N1	0.1942 (2)	0.30801 (12)	0.51522 (8)	0.0408 (4)
N2	0.1579 (2)	0.13389 (15)	0.72451 (9)	0.0471 (5)
O1	0.1521 (2)	0.20292 (13)	0.42413 (8)	0.0671 (5)
O2	0.27674 (18)	0.13467 (11)	0.51672 (8)	0.0541 (4)
O3	0.06190 (19)	0.20056 (13)	0.72205 (10)	0.0683 (5)
O4	0.1284 (2)	0.04933 (13)	0.70995 (10)	0.0692 (5)
O5	0.20795 (17)	0.56420 (10)	0.65879 (7)	0.0428 (4)
O6	0.74881 (19)	0.20527 (10)	0.82589 (8)	0.0504 (4)
O7	0.60017 (16)	0.04943 (10)	0.85569 (7)	0.0455 (4)
S1	0.16035 (6)	0.19526 (4)	0.48928 (3)	0.04579 (14)

	U11	U22	U33	U12	U13	U23
C1	0.0372 (10)	0.0503 (12)	0.0357 (10)	−0.0021 (9)	0.0023 (10)	0.0052 (11)
C2	0.0557 (14)	0.0690 (17)	0.0406 (12)	−0.0028 (12)	−0.0034 (11)	0.0012 (12)
C3	0.0546 (15)	0.083 (2)	0.0439 (14)	0.0040 (12)	−0.0075 (11)	0.0171 (14)
C4	0.0493 (13)	0.0633 (15)	0.0525 (14)	0.0125 (11)	0.0033 (11)	0.0211 (13)
C5	0.0378 (11)	0.0542 (14)	0.0471 (12)	0.0084 (10)	0.0046 (10)	0.0099 (11)
C6	0.0289 (9)	0.0470 (13)	0.0345 (10)	0.0009 (8)	0.0033 (8)	0.0066 (9)
C7	0.0293 (9)	0.0342 (10)	0.0371 (10)	0.0004 (7)	0.0046 (8)	0.0038 (9)
C8	0.0322 (9)	0.0318 (10)	0.0378 (10)	0.0031 (8)	0.0068 (8)	−0.0018 (9)
C9	0.0407 (11)	0.0367 (12)	0.0357 (11)	0.0023 (8)	0.0015 (9)	−0.0015 (9)
C10	0.0359 (10)	0.0343 (11)	0.0342 (11)	0.0013 (8)	−0.0005 (8)	0.0014 (8)
C11	0.0399 (10)	0.0294 (10)	0.0395 (11)	0.0014 (8)	0.0030 (9)	−0.0018 (9)
C12	0.0330 (9)	0.0391 (11)	0.0297 (10)	−0.0012 (8)	0.0014 (8)	−0.0022 (9)
C13	0.0400 (10)	0.0325 (10)	0.0330 (10)	0.0026 (8)	0.0014 (8)	0.0006 (9)
C14	0.0471 (11)	0.0310 (11)	0.0368 (10)	−0.0018 (8)	0.0006 (9)	0.0035 (9)
C15	0.0360 (10)	0.0370 (11)	0.0386 (11)	0.0020 (8)	−0.0013 (9)	−0.0010 (9)
C16	0.0411 (10)	0.0308 (10)	0.0350 (11)	0.0065 (8)	0.0029 (9)	0.0049 (8)
C17	0.0417 (11)	0.0323 (10)	0.0400 (11)	0.0004 (8)	0.0051 (9)	0.0034 (9)
C18	0.0373 (10)	0.0363 (11)	0.0359 (11)	0.0014 (8)	0.0028 (8)	0.0000 (9)
C19	0.0444 (11)	0.0399 (12)	0.0537 (14)	−0.0001 (9)	−0.0046 (10)	−0.0154 (11)
C20	0.0592 (14)	0.0596 (15)	0.0703 (17)	0.0035 (12)	−0.0182 (14)	−0.0069 (14)
C21	0.0431 (14)	0.0681 (18)	0.115 (3)	−0.0007 (12)	−0.0155 (16)	−0.0148 (19)
C22	0.0527 (15)	0.0513 (16)	0.129 (3)	−0.0095 (12)	0.0142 (17)	−0.0140 (19)
C23	0.0725 (19)	0.0544 (16)	0.092 (2)	−0.0164 (14)	0.0137 (17)	0.0051 (15)
C24	0.0554 (13)	0.0466 (13)	0.0656 (16)	−0.0056 (11)	−0.0042 (12)	−0.0011 (12)
C25	0.0567 (14)	0.0394 (13)	0.0694 (17)	−0.0036 (10)	0.0125 (12)	−0.0006 (12)
C26	0.0780 (16)	0.0458 (14)	0.0410 (12)	0.0101 (11)	−0.0101 (12)	−0.0104 (11)
C27	0.0565 (14)	0.0532 (15)	0.0638 (16)	−0.0152 (11)	−0.0083 (12)	0.0003 (12)
C28	0.0570 (14)	0.0509 (14)	0.0706 (18)	0.0004 (11)	−0.0063 (12)	0.0275 (13)
N1	0.0461 (10)	0.0447 (10)	0.0317 (8)	−0.0019 (7)	−0.0011 (7)	−0.0021 (8)
N2	0.0430 (11)	0.0565 (13)	0.0418 (10)	−0.0035 (9)	0.0000 (8)	0.0088 (9)
O1	0.0784 (13)	0.0811 (13)	0.0417 (9)	−0.0006 (9)	0.0010 (9)	−0.0197 (9)
O2	0.0481 (8)	0.0516 (9)	0.0628 (10)	0.0097 (7)	−0.0031 (8)	−0.0177 (8)
O3	0.0396 (9)	0.0782 (13)	0.0870 (14)	0.0143 (8)	0.0000 (9)	0.0079 (11)
O4	0.0657 (11)	0.0574 (11)	0.0844 (14)	−0.0209 (9)	−0.0219 (10)	0.0096 (10)
O5	0.0463 (8)	0.0325 (8)	0.0497 (9)	0.0076 (6)	0.0090 (7)	−0.0014 (7)
O6	0.0490 (8)	0.0470 (9)	0.0553 (9)	−0.0077 (7)	−0.0142 (7)	0.0117 (7)
O7	0.0442 (8)	0.0384 (8)	0.0539 (9)	0.0018 (6)	−0.0056 (7)	0.0142 (7)
S1	0.0466 (3)	0.0508 (3)	0.0399 (3)	0.0019 (2)	−0.0005 (3)	−0.0144 (3)

C1—C2	1.385 (3)	C18—N2	1.465 (3)
C1—C6	1.395 (3)	C19—C20	1.376 (3)
C1—N1	1.427 (3)	C19—C24	1.385 (3)
C2—C3	1.376 (4)	C19—S1	1.752 (2)
C2—H2	0.9300	C20—C21	1.386 (4)
C3—C4	1.385 (4)	C20—H20	0.9300
C3—H3	0.9300	C21—C22	1.366 (5)
C4—C5	1.376 (3)	C21—H21	0.9300
C4—H4	0.9300	C22—C23	1.368 (4)
C5—C6	1.395 (3)	C22—H22	0.9300
C5—H5	0.9300	C23—C24	1.383 (4)
C6—C7	1.449 (3)	C23—H23	0.9300
C7—C8	1.385 (3)	C24—H24	0.9300
C7—C12	1.404 (3)	C25—O5	1.437 (3)
C8—O5	1.389 (2)	C25—H25A	0.9600
C8—C9	1.389 (3)	C25—H25B	0.9600
C9—C10	1.407 (3)	C25—H25C	0.9600
C9—C26	1.500 (3)	C26—H26A	0.9600
C10—C11	1.390 (3)	C26—H26B	0.9600
C10—C13	1.495 (3)	C26—H26C	0.9600
C11—C12	1.380 (3)	C27—O6	1.423 (3)
C11—H11	0.9300	C27—H27A	0.9600
C12—N1	1.425 (3)	C27—H27B	0.9600
C13—C18	1.391 (3)	C27—H27C	0.9600
C13—C14	1.399 (3)	C28—O7	1.424 (3)
C14—C15	1.388 (3)	C28—H28A	0.9600
C14—H14	0.9300	C28—H28B	0.9600
C15—O6	1.351 (3)	C28—H28C	0.9600
C15—C16	1.401 (3)	N1—S1	1.6641 (18)
C16—O7	1.355 (2)	N2—O3	1.221 (2)
C16—C17	1.375 (3)	N2—O4	1.223 (2)
C17—C18	1.379 (3)	O1—S1	1.4152 (18)
C17—H17	0.9300	O2—S1	1.4163 (16)
C2—C1—C6	121.8 (2)	C24—C19—S1	118.54 (18)
C2—C1—N1	129.5 (2)	C19—C20—C21	118.7 (3)
C6—C1—N1	108.66 (18)	C19—C20—H20	120.6
C3—C2—C1	117.4 (2)	C21—C20—H20	120.6
C3—C2—H2	121.3	C22—C21—C20	120.4 (3)
C1—C2—H2	121.3	C22—C21—H21	119.8
C2—C3—C4	121.7 (2)	C20—C21—H21	119.8
C2—C3—H3	119.2	C21—C22—C23	120.6 (3)
C4—C3—H3	119.2	C21—C22—H22	119.7
C5—C4—C3	121.0 (2)	C23—C22—H22	119.7
C5—C4—H4	119.5	C22—C23—C24	120.3 (3)
C3—C4—H4	119.5	C22—C23—H23	119.9
C4—C5—C6	118.5 (2)	C24—C23—H23	119.9
C4—C5—H5	120.8	C23—C24—C19	118.8 (3)
C6—C5—H5	120.8	C23—C24—H24	120.6
C5—C6—C1	119.66 (19)	C19—C24—H24	120.6
C5—C6—C7	132.7 (2)	O5—C25—H25A	109.5
C1—C6—C7	107.68 (18)	O5—C25—H25B	109.5
C8—C7—C12	118.70 (17)	H25A—C25—H25B	109.5
C8—C7—C6	133.51 (18)	O5—C25—H25C	109.5
C12—C7—C6	107.72 (18)	H25A—C25—H25C	109.5
C7—C8—O5	119.31 (17)	H25B—C25—H25C	109.5
C7—C8—C9	121.26 (17)	C9—C26—H26A	109.5
O5—C8—C9	119.29 (18)	C9—C26—H26B	109.5
C8—C9—C10	118.44 (18)	H26A—C26—H26B	109.5
C8—C9—C26	119.60 (18)	C9—C26—H26C	109.5
C10—C9—C26	121.93 (19)	H26A—C26—H26C	109.5
C11—C10—C9	121.41 (18)	H26B—C26—H26C	109.5
C11—C10—C13	117.40 (17)	O6—C27—H27A	109.5
C9—C10—C13	121.19 (18)	O6—C27—H27B	109.5
C12—C11—C10	118.44 (18)	H27A—C27—H27B	109.5
C12—C11—H11	120.8	O6—C27—H27C	109.5
C10—C11—H11	120.8	H27A—C27—H27C	109.5
C11—C12—C7	121.64 (18)	H27B—C27—H27C	109.5
C11—C12—N1	130.06 (18)	O7—C28—H28A	109.5
C7—C12—N1	108.29 (16)	O7—C28—H28B	109.5
C18—C13—C14	116.04 (18)	H28A—C28—H28B	109.5
C18—C13—C10	123.34 (17)	O7—C28—H28C	109.5
C14—C13—C10	120.43 (17)	H28A—C28—H28C	109.5
C15—C14—C13	121.47 (18)	H28B—C28—H28C	109.5
C15—C14—H14	119.3	C12—N1—C1	107.51 (16)
C13—C14—H14	119.3	C12—N1—S1	123.55 (14)
O6—C15—C14	125.07 (18)	C1—N1—S1	124.66 (15)
O6—C15—C16	114.73 (17)	O3—N2—O4	123.89 (19)
C14—C15—C16	120.20 (19)	O3—N2—C18	118.41 (19)
O7—C16—C17	124.92 (18)	O4—N2—C18	117.69 (18)
O7—C16—C15	115.74 (17)	C8—O5—C25	113.57 (15)
C17—C16—C15	119.34 (18)	C15—O6—C27	118.00 (16)
C16—C17—C18	119.19 (19)	C16—O7—C28	117.58 (16)
C16—C17—H17	120.4	O1—S1—O2	119.67 (11)
C18—C17—H17	120.4	O1—S1—N1	106.02 (10)
C17—C18—C13	123.73 (19)	O2—S1—N1	106.26 (9)
C17—C18—N2	116.19 (19)	O1—S1—C19	109.43 (11)
C13—C18—N2	120.06 (17)	O2—S1—C19	109.35 (11)
C20—C19—C24	121.2 (2)	N1—S1—C19	105.07 (10)
C20—C19—S1	120.2 (2)
C6—C1—C2—C3	−0.8 (3)	O7—C16—C17—C18	178.08 (18)
N1—C1—C2—C3	−179.3 (2)	C15—C16—C17—C18	−1.6 (3)
C1—C2—C3—C4	1.4 (3)	C16—C17—C18—C13	2.1 (3)
C2—C3—C4—C5	−1.3 (4)	C16—C17—C18—N2	−175.98 (17)
C3—C4—C5—C6	0.6 (3)	C14—C13—C18—C17	−0.8 (3)
C4—C5—C6—C1	−0.1 (3)	C10—C13—C18—C17	174.25 (19)
C4—C5—C6—C7	−178.9 (2)	C14—C13—C18—N2	177.23 (18)
C2—C1—C6—C5	0.1 (3)	C10—C13—C18—N2	−7.7 (3)
N1—C1—C6—C5	178.92 (17)	C24—C19—C20—C21	0.3 (4)
C2—C1—C6—C7	179.23 (18)	S1—C19—C20—C21	−178.4 (2)
N1—C1—C6—C7	−2.0 (2)	C19—C20—C21—C22	−0.1 (4)
C5—C6—C7—C8	1.7 (4)	C20—C21—C22—C23	0.4 (5)
C1—C6—C7—C8	−177.3 (2)	C21—C22—C23—C24	−1.0 (4)
C5—C6—C7—C12	178.6 (2)	C22—C23—C24—C19	1.1 (4)
C1—C6—C7—C12	−0.4 (2)	C20—C19—C24—C23	−0.8 (4)
C12—C7—C8—O5	−177.72 (16)	S1—C19—C24—C23	177.9 (2)
C6—C7—C8—O5	−1.1 (3)	C11—C12—N1—C1	177.16 (19)
C12—C7—C8—C9	−2.1 (3)	C7—C12—N1—C1	−3.8 (2)
C6—C7—C8—C9	174.50 (19)	C11—C12—N1—S1	19.6 (3)
C7—C8—C9—C10	2.8 (3)	C7—C12—N1—S1	−161.39 (14)
O5—C8—C9—C10	178.40 (17)	C2—C1—N1—C12	−177.8 (2)
C7—C8—C9—C26	−175.18 (19)	C6—C1—N1—C12	3.6 (2)
O5—C8—C9—C26	0.4 (3)	C2—C1—N1—S1	−20.5 (3)
C8—C9—C10—C11	−0.6 (3)	C6—C1—N1—S1	160.86 (15)
C26—C9—C10—C11	177.4 (2)	C17—C18—N2—O3	136.5 (2)
C8—C9—C10—C13	179.35 (18)	C13—C18—N2—O3	−41.7 (3)
C26—C9—C10—C13	−2.7 (3)	C17—C18—N2—O4	−42.5 (3)
C9—C10—C11—C12	−2.3 (3)	C13—C18—N2—O4	139.3 (2)
C13—C10—C11—C12	177.81 (17)	C7—C8—O5—C25	−84.7 (2)
C10—C11—C12—C7	3.0 (3)	C9—C8—O5—C25	99.6 (2)
C10—C11—C12—N1	−178.07 (19)	C14—C15—O6—C27	8.8 (3)
C8—C7—C12—C11	−0.8 (3)	C16—C15—O6—C27	−170.76 (19)
C6—C7—C12—C11	−178.28 (16)	C17—C16—O7—C28	−7.8 (3)
C8—C7—C12—N1	−179.98 (16)	C15—C16—O7—C28	171.89 (19)
C6—C7—C12—N1	2.6 (2)	C12—N1—S1—O1	−168.45 (17)
C11—C10—C13—C18	−57.7 (3)	C1—N1—S1—O1	37.77 (19)
C9—C10—C13—C18	122.3 (2)	C12—N1—S1—O2	−40.13 (18)
C11—C10—C13—C14	117.1 (2)	C1—N1—S1—O2	166.09 (17)
C9—C10—C13—C14	−62.8 (3)	C12—N1—S1—C19	75.72 (18)
C18—C13—C14—C15	−1.0 (3)	C1—N1—S1—C19	−78.07 (19)
C10—C13—C14—C15	−176.19 (19)	C20—C19—S1—O1	−24.4 (2)
C13—C14—C15—O6	−178.05 (19)	C24—C19—S1—O1	156.87 (19)
C13—C14—C15—C16	1.4 (3)	C20—C19—S1—O2	−157.29 (18)
O6—C15—C16—O7	−0.3 (3)	C24—C19—S1—O2	24.0 (2)
C14—C15—C16—O7	−179.81 (18)	C20—C19—S1—N1	89.0 (2)
O6—C15—C16—C17	179.45 (18)	C24—C19—S1—N1	−89.7 (2)
C14—C15—C16—C17	−0.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1	0.93	2.34	2.937 (3)	122
C11—H11···O2	0.93	2.34	2.939 (2)	122
C17—H17···O7i	0.93	2.55	3.372 (2)	148
C27—H27A···O3ii	0.96	2.59	3.167 (3)	119

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1	0.93	2.34	2.937 (3)	122
C11—H11⋯O2	0.93	2.34	2.939 (2)	122
C17—H17⋯O7i	0.93	2.55	3.372 (2)	148
C27—H27A⋯O3ii	0.96	2.59	3.167 (3)	119

Symmetry codes: (i) ; (ii) .