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

In the title compound, C28H22N2O8S, the carbazole ring system is roughly planar, with a maximum deviation of 0.084 (3) Å for the C atom connected to the 4,5-dimeth-oxy-2-nitro-phenyl ring. The dihedral angle between the carbazole system and the dimeth-oxy-substituted nitro-phenyl ring is 57.05 (10)°. The aldehyde C atom deviates by 0.164 (5) Å from its attached carbazole ring system. The mol-ecular structure is stabilized by C-H⋯O inter-actions which generate two S(6) and one S(7) ring motif. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds, forming R 3 (3)(15) ring motifs, which are further crosslinked by R 3 (2)(19) ring motifs, resulting in (002) layers. The crystal packing also features C-H⋯π inter-actions.

Related literature

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

Experimental

Crystal data

C28H22N2O8S

M = 546.55

Orthorhombic,

a = 8.3976 (6) Å

b = 13.7584 (9) Å

c = 21.7971 (12) Å

V = 2518.4 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.19 mm−1

T = 295 K

0.25 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.949, T max = 0.971

16717 measured reflections

5538 independent reflections

4047 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.115

S = 1.01

5538 reflections

355 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.35 e Å−3

Absolute structure: Flack (1983 ▶)

Absolute structure parameter: 0.02 (8)

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2008 ▶); 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/S1600536814005133/rk2423sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814005133/rk2423Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814005133/rk2423Isup3.cml

CCDC reference: 990378

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

C28H22N2O8S	Dx = 1.441 Mg m−3
Mr = 546.55	Melting point = 471–473 K
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 4047 reflections
a = 8.3976 (6) Å	θ = 2.4–29.9°
b = 13.7584 (9) Å	µ = 0.19 mm−1
c = 21.7971 (12) Å	T = 295 K
V = 2518.4 (3) Å3	Block, colourless
Z = 4	0.25 × 0.25 × 0.20 mm
F(000) = 1136

Bruker Kappa APEX–II CCD diffractometer	5538 independent reflections
Radiation source: fine–focus sealed tube	4047 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
ω– & φ–scans	θmax = 29.9°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −11→11
Tmin = 0.949, Tmax = 0.971	k = −19→12
16717 measured reflections	l = −16→30

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043	H-atom parameters constrained
wR(F2) = 0.115	w = 1/[σ2(Fo2) + (0.059P)2 + 0.2808P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
5538 reflections	Δρmax = 0.37 e Å−3
355 parameters	Δρmin = −0.35 e Å−3
2 restraints	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.02 (8)

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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	0.8650 (3)	0.1054 (2)	0.40810 (13)	0.0448 (6)
C2	0.9302 (4)	0.0894 (3)	0.35094 (14)	0.0615 (8)
H2	0.9377	0.1391	0.3221	0.074*
C3	0.9838 (4)	−0.0031 (3)	0.33812 (16)	0.0708 (10)
H3	1.0298	−0.0156	0.3001	0.085*
C4	0.9712 (4)	−0.0772 (3)	0.37992 (15)	0.0598 (8)
H4	1.0067	−0.1391	0.3694	0.072*
C5	0.9070 (3)	−0.0617 (2)	0.43698 (14)	0.0511 (7)
H5	0.8994	−0.1121	0.4652	0.061*
C6	0.8536 (3)	0.0312 (2)	0.45165 (12)	0.0396 (6)
C7	0.7830 (3)	0.07281 (18)	0.50642 (12)	0.0366 (5)
C8	0.7490 (3)	0.03425 (17)	0.56383 (12)	0.0371 (5)
C9	0.6929 (3)	0.09573 (19)	0.61001 (12)	0.0434 (6)
C10	0.6676 (3)	0.19546 (18)	0.59770 (12)	0.0382 (5)
C11	0.6948 (3)	0.23323 (19)	0.53996 (12)	0.0391 (6)
H11	0.6732	0.2981	0.5313	0.047*
C12	0.7553 (3)	0.17175 (18)	0.49529 (11)	0.0365 (5)
C13	0.6053 (3)	0.26215 (18)	0.64630 (12)	0.0387 (5)
C14	0.4585 (3)	0.24500 (19)	0.67360 (12)	0.0419 (6)
H14	0.4016	0.1895	0.6630	0.050*
C15	0.3949 (3)	0.30877 (18)	0.71640 (13)	0.0417 (6)
C16	0.4779 (3)	0.39378 (19)	0.73222 (11)	0.0393 (5)
C17	0.6221 (3)	0.41252 (19)	0.70510 (12)	0.0408 (6)
H17	0.6778	0.4690	0.7146	0.049*
C18	0.6841 (3)	0.34688 (19)	0.66353 (12)	0.0401 (6)
C19	1.0216 (3)	0.3359 (2)	0.43564 (14)	0.0496 (7)
C20	1.1564 (4)	0.3137 (2)	0.4026 (2)	0.0661 (9)
H20	1.1486	0.2835	0.3646	0.079*
C21	1.3031 (4)	0.3368 (3)	0.4268 (2)	0.0798 (12)
H21	1.3949	0.3226	0.4047	0.096*
C22	1.3149 (4)	0.3804 (3)	0.4830 (2)	0.0792 (12)
H22	1.4146	0.3946	0.4993	0.095*
C23	1.1808 (5)	0.4032 (3)	0.5151 (2)	0.0798 (11)
H23	1.1896	0.4341	0.5529	0.096*
C24	1.0324 (4)	0.3809 (2)	0.49226 (17)	0.0599 (8)
H24	0.9410	0.3957	0.5145	0.072*
C25	0.6625 (4)	−0.1291 (2)	0.55932 (18)	0.0603 (8)
H25A	0.6311	−0.1181	0.5176	0.090*
H25B	0.5721	−0.1210	0.5858	0.090*
H25C	0.7031	−0.1940	0.5634	0.090*
C26	0.6670 (6)	0.0594 (3)	0.67271 (17)	0.0833 (12)
H26	0.7082	0.0952	0.7052	0.100*
C27	0.1723 (4)	0.2068 (2)	0.73733 (17)	0.0636 (9)
H27A	0.2407	0.1538	0.7485	0.095*
H27B	0.1418	0.2005	0.6951	0.095*
H27C	0.0788	0.2058	0.7627	0.095*
C28	0.4937 (4)	0.5310 (2)	0.79770 (17)	0.0663 (9)
H28A	0.5144	0.5765	0.7653	0.099*
H28B	0.5928	0.5081	0.8142	0.099*
H28C	0.4335	0.5623	0.8295	0.099*
N1	0.8002 (3)	0.19235 (16)	0.43400 (11)	0.0443 (5)
N2	0.8427 (3)	0.3687 (2)	0.63994 (11)	0.0508 (6)
O1	0.8401 (3)	0.2956 (2)	0.34239 (11)	0.0744 (7)
O2	0.7169 (2)	0.36484 (15)	0.43482 (11)	0.0597 (5)
O3	0.9392 (3)	0.30255 (18)	0.63549 (13)	0.0732 (7)
O4	0.8724 (3)	0.45314 (18)	0.62628 (12)	0.0744 (7)
O5	0.7846 (2)	−0.06046 (13)	0.57617 (9)	0.0473 (5)
O6	0.2548 (3)	0.29660 (14)	0.74591 (10)	0.0550 (5)
O7	0.4055 (2)	0.45109 (14)	0.77418 (9)	0.0497 (5)
O8	0.5939 (8)	−0.0159 (2)	0.68447 (18)	0.168 (2)
S1	0.83364 (8)	0.30432 (5)	0.40724 (4)	0.05068 (19)

	U11	U22	U33	U12	U13	U23
C1	0.0412 (13)	0.0577 (17)	0.0356 (13)	−0.0009 (12)	−0.0036 (11)	−0.0048 (13)
C2	0.0640 (19)	0.079 (2)	0.0416 (17)	−0.0063 (17)	0.0054 (14)	−0.0041 (15)
C3	0.063 (2)	0.102 (3)	0.0476 (19)	0.0011 (19)	0.0092 (15)	−0.0243 (19)
C4	0.0575 (18)	0.069 (2)	0.0532 (19)	0.0106 (15)	−0.0038 (14)	−0.0212 (16)
C5	0.0435 (14)	0.0604 (18)	0.0495 (17)	0.0090 (13)	−0.0059 (12)	−0.0139 (14)
C6	0.0319 (12)	0.0496 (16)	0.0372 (14)	0.0014 (11)	−0.0048 (9)	−0.0059 (11)
C7	0.0321 (11)	0.0412 (13)	0.0367 (13)	0.0015 (10)	−0.0052 (9)	−0.0046 (10)
C8	0.0418 (13)	0.0336 (13)	0.0358 (13)	0.0038 (11)	−0.0059 (10)	−0.0001 (10)
C9	0.0535 (15)	0.0396 (14)	0.0369 (14)	0.0042 (12)	−0.0008 (11)	0.0023 (11)
C10	0.0444 (13)	0.0344 (13)	0.0358 (14)	0.0015 (11)	0.0004 (10)	−0.0023 (10)
C11	0.0442 (13)	0.0333 (13)	0.0397 (14)	0.0042 (11)	−0.0053 (11)	0.0003 (11)
C12	0.0371 (11)	0.0414 (14)	0.0311 (13)	−0.0015 (11)	−0.0049 (9)	0.0038 (10)
C13	0.0473 (14)	0.0354 (13)	0.0334 (13)	0.0037 (11)	−0.0032 (10)	0.0016 (10)
C14	0.0547 (15)	0.0324 (13)	0.0387 (14)	−0.0034 (11)	−0.0003 (11)	−0.0033 (10)
C15	0.0460 (13)	0.0398 (14)	0.0395 (14)	0.0009 (11)	0.0019 (11)	0.0026 (11)
C16	0.0452 (13)	0.0356 (13)	0.0370 (14)	0.0048 (11)	−0.0026 (10)	−0.0033 (10)
C17	0.0459 (13)	0.0328 (12)	0.0437 (15)	0.0005 (11)	−0.0039 (11)	−0.0010 (11)
C18	0.0422 (13)	0.0408 (15)	0.0372 (14)	0.0006 (11)	−0.0010 (10)	−0.0009 (11)
C19	0.0480 (14)	0.0421 (15)	0.0588 (19)	0.0000 (12)	0.0029 (13)	0.0186 (14)
C20	0.0587 (18)	0.068 (2)	0.072 (2)	0.0017 (16)	0.0180 (16)	0.0060 (18)
C21	0.0464 (18)	0.070 (2)	0.123 (4)	−0.0021 (17)	0.020 (2)	0.011 (2)
C22	0.0528 (19)	0.056 (2)	0.129 (4)	−0.0050 (16)	−0.009 (2)	0.013 (2)
C23	0.073 (2)	0.062 (2)	0.104 (3)	−0.0222 (19)	−0.012 (2)	−0.004 (2)
C24	0.0561 (17)	0.0543 (18)	0.069 (2)	−0.0086 (14)	0.0060 (15)	0.0004 (16)
C25	0.0645 (19)	0.0419 (16)	0.075 (2)	−0.0013 (14)	−0.0089 (16)	0.0048 (15)
C26	0.157 (4)	0.0522 (18)	0.0410 (18)	0.0338 (19)	0.011 (2)	0.0073 (16)
C27	0.0669 (19)	0.058 (2)	0.065 (2)	−0.0191 (16)	0.0083 (15)	0.0023 (15)
C28	0.0626 (19)	0.0521 (19)	0.084 (3)	−0.0076 (15)	0.0101 (16)	−0.0333 (17)
N1	0.0502 (12)	0.0490 (13)	0.0336 (12)	−0.0035 (10)	0.0008 (9)	0.0015 (10)
N2	0.0500 (14)	0.0579 (16)	0.0446 (14)	−0.0007 (12)	0.0018 (10)	−0.0125 (11)
O1	0.0811 (17)	0.0983 (19)	0.0439 (14)	−0.0043 (13)	−0.0030 (11)	0.0244 (12)
O2	0.0505 (11)	0.0575 (12)	0.0710 (14)	0.0094 (9)	−0.0002 (10)	0.0204 (11)
O3	0.0489 (12)	0.0819 (17)	0.0890 (19)	0.0147 (12)	0.0014 (12)	−0.0089 (13)
O4	0.0733 (15)	0.0623 (15)	0.0878 (19)	−0.0204 (12)	0.0230 (13)	−0.0121 (13)
O5	0.0556 (11)	0.0359 (10)	0.0504 (12)	0.0089 (8)	−0.0117 (8)	−0.0006 (8)
O6	0.0559 (11)	0.0523 (12)	0.0570 (13)	−0.0130 (10)	0.0151 (9)	−0.0105 (9)
O7	0.0508 (10)	0.0424 (11)	0.0559 (12)	0.0031 (9)	0.0052 (9)	−0.0143 (9)
O8	0.346 (7)	0.068 (2)	0.090 (3)	−0.015 (3)	0.072 (3)	0.0203 (17)
S1	0.0495 (4)	0.0595 (5)	0.0431 (4)	0.0009 (3)	−0.0010 (3)	0.0174 (3)

C1—C2	1.379 (4)	C18—N2	1.459 (4)
C1—C6	1.398 (4)	C19—C20	1.376 (4)
C1—N1	1.430 (3)	C19—C24	1.383 (5)
C2—C3	1.379 (5)	C19—S1	1.751 (3)
C2—H2	0.9300	C20—C21	1.377 (5)
C3—C4	1.371 (5)	C20—H20	0.9300
C3—H3	0.9300	C21—C22	1.368 (7)
C4—C5	1.372 (4)	C21—H21	0.9300
C4—H4	0.9300	C22—C23	1.363 (6)
C5—C6	1.391 (4)	C22—H22	0.9300
C5—H5	0.9300	C23—C24	1.377 (5)
C6—C7	1.451 (3)	C23—H23	0.9300
C7—C8	1.389 (4)	C24—H24	0.9300
C7—C12	1.402 (3)	C25—O5	1.442 (4)
C8—O5	1.364 (3)	C25—H25A	0.9600
C8—C9	1.397 (4)	C25—H25B	0.9600
C9—C10	1.414 (3)	C25—H25C	0.9600
C9—C26	1.471 (4)	C26—O8	1.231 (5)
C10—C11	1.381 (4)	C26—H26	0.9300
C10—C13	1.496 (4)	C27—O6	1.429 (3)
C11—C12	1.386 (4)	C27—H27A	0.9600
C11—H11	0.9300	C27—H27B	0.9600
C12—N1	1.417 (3)	C27—H27C	0.9600
C13—C14	1.388 (4)	C28—O7	1.422 (3)
C13—C18	1.392 (4)	C28—H28A	0.9600
C14—C15	1.388 (4)	C28—H28B	0.9600
C14—H14	0.9300	C28—H28C	0.9600
C15—O6	1.351 (3)	N1—S1	1.671 (2)
C15—C16	1.404 (4)	N2—O3	1.223 (3)
C16—O7	1.352 (3)	N2—O4	1.225 (3)
C16—C17	1.372 (4)	O1—S1	1.420 (2)
C17—C18	1.381 (4)	O2—S1	1.420 (2)
C17—H17	0.9300
C2—C1—C6	121.6 (3)	C20—C19—C24	120.8 (3)
C2—C1—N1	129.9 (3)	C20—C19—S1	120.1 (3)
C6—C1—N1	108.5 (2)	C24—C19—S1	119.0 (2)
C1—C2—C3	117.4 (3)	C19—C20—C21	119.0 (4)
C1—C2—H2	121.3	C19—C20—H20	120.5
C3—C2—H2	121.3	C21—C20—H20	120.5
C4—C3—C2	121.8 (3)	C22—C21—C20	120.6 (4)
C4—C3—H3	119.1	C22—C21—H21	119.7
C2—C3—H3	119.1	C20—C21—H21	119.7
C3—C4—C5	121.1 (3)	C23—C22—C21	120.1 (4)
C3—C4—H4	119.4	C23—C22—H22	120.0
C5—C4—H4	119.4	C21—C22—H22	120.0
C4—C5—C6	118.6 (3)	C22—C23—C24	120.7 (4)
C4—C5—H5	120.7	C22—C23—H23	119.6
C6—C5—H5	120.7	C24—C23—H23	119.6
C5—C6—C1	119.5 (2)	C23—C24—C19	118.8 (3)
C5—C6—C7	133.1 (3)	C23—C24—H24	120.6
C1—C6—C7	107.4 (2)	C19—C24—H24	120.6
C8—C7—C12	119.5 (2)	O5—C25—H25A	109.5
C8—C7—C6	132.4 (2)	O5—C25—H25B	109.5
C12—C7—C6	108.0 (2)	H25A—C25—H25B	109.5
O5—C8—C7	119.9 (2)	O5—C25—H25C	109.5
O5—C8—C9	120.7 (2)	H25A—C25—H25C	109.5
C7—C8—C9	119.2 (2)	H25B—C25—H25C	109.5
C8—C9—C10	120.1 (2)	O8—C26—C9	123.6 (4)
C8—C9—C26	120.9 (2)	O8—C26—H26	118.2
C10—C9—C26	118.9 (2)	C9—C26—H26	118.2
C11—C10—C9	120.9 (2)	O6—C27—H27A	109.5
C11—C10—C13	118.2 (2)	O6—C27—H27B	109.5
C9—C10—C13	120.9 (2)	H27A—C27—H27B	109.5
C10—C11—C12	118.1 (2)	O6—C27—H27C	109.5
C10—C11—H11	120.9	H27A—C27—H27C	109.5
C12—C11—H11	120.9	H27B—C27—H27C	109.5
C11—C12—C7	122.1 (2)	O7—C28—H28A	109.5
C11—C12—N1	129.6 (2)	O7—C28—H28B	109.5
C7—C12—N1	108.3 (2)	H28A—C28—H28B	109.5
C14—C13—C18	116.7 (2)	O7—C28—H28C	109.5
C14—C13—C10	120.6 (2)	H28A—C28—H28C	109.5
C18—C13—C10	122.6 (2)	H28B—C28—H28C	109.5
C15—C14—C13	121.5 (2)	C12—N1—C1	107.8 (2)
C15—C14—H14	119.3	C12—N1—S1	123.94 (18)
C13—C14—H14	119.3	C1—N1—S1	124.68 (19)
O6—C15—C14	125.2 (2)	O3—N2—O4	123.5 (3)
O6—C15—C16	114.7 (2)	O3—N2—C18	118.7 (3)
C14—C15—C16	120.0 (2)	O4—N2—C18	117.9 (2)
O7—C16—C17	125.4 (2)	C8—O5—C25	114.8 (2)
O7—C16—C15	115.4 (2)	C15—O6—C27	117.9 (2)
C17—C16—C15	119.2 (2)	C16—O7—C28	117.4 (2)
C16—C17—C18	119.5 (2)	O1—S1—O2	119.83 (15)
C16—C17—H17	120.3	O1—S1—N1	106.05 (14)
C18—C17—H17	120.3	O2—S1—N1	106.06 (12)
C17—C18—C13	123.1 (2)	O1—S1—C19	109.79 (15)
C17—C18—N2	116.1 (2)	O2—S1—C19	109.09 (15)
C13—C18—N2	120.8 (2)	N1—S1—C19	104.91 (12)
C6—C1—C2—C3	0.1 (4)	C15—C16—C17—C18	−1.0 (4)
N1—C1—C2—C3	−179.8 (3)	C16—C17—C18—C13	1.4 (4)
C1—C2—C3—C4	1.0 (5)	C16—C17—C18—N2	−175.9 (2)
C2—C3—C4—C5	−1.3 (5)	C14—C13—C18—C17	−0.6 (4)
C3—C4—C5—C6	0.4 (4)	C10—C13—C18—C17	175.2 (2)
C4—C5—C6—C1	0.6 (4)	C14—C13—C18—N2	176.7 (2)
C4—C5—C6—C7	−179.2 (3)	C10—C13—C18—N2	−7.6 (4)
C2—C1—C6—C5	−0.9 (4)	C24—C19—C20—C21	0.0 (5)
N1—C1—C6—C5	179.0 (2)	S1—C19—C20—C21	−178.1 (3)
C2—C1—C6—C7	178.9 (2)	C19—C20—C21—C22	0.6 (5)
N1—C1—C6—C7	−1.1 (3)	C20—C21—C22—C23	−1.3 (6)
C5—C6—C7—C8	2.3 (4)	C21—C22—C23—C24	1.4 (6)
C1—C6—C7—C8	−177.5 (2)	C22—C23—C24—C19	−0.8 (6)
C5—C6—C7—C12	178.9 (3)	C20—C19—C24—C23	0.1 (5)
C1—C6—C7—C12	−0.9 (3)	S1—C19—C24—C23	178.2 (3)
C12—C7—C8—O5	−176.0 (2)	C8—C9—C26—O8	−48.4 (6)
C6—C7—C8—O5	0.3 (4)	C10—C9—C26—O8	134.7 (4)
C12—C7—C8—C9	−2.1 (3)	C11—C12—N1—C1	176.3 (2)
C6—C7—C8—C9	174.2 (2)	C7—C12—N1—C1	−3.2 (3)
O5—C8—C9—C10	175.3 (2)	C11—C12—N1—S1	16.8 (4)
C7—C8—C9—C10	1.5 (4)	C7—C12—N1—S1	−162.79 (18)
O5—C8—C9—C26	−1.5 (4)	C2—C1—N1—C12	−177.3 (3)
C7—C8—C9—C26	−175.3 (3)	C6—C1—N1—C12	2.7 (3)
C8—C9—C10—C11	1.2 (4)	C2—C1—N1—S1	−18.0 (4)
C26—C9—C10—C11	178.1 (3)	C6—C1—N1—S1	162.05 (18)
C8—C9—C10—C13	179.1 (2)	C17—C18—N2—O3	137.1 (3)
C26—C9—C10—C13	−4.0 (4)	C13—C18—N2—O3	−40.3 (4)
C9—C10—C11—C12	−3.2 (4)	C17—C18—N2—O4	−42.0 (3)
C13—C10—C11—C12	178.8 (2)	C13—C18—N2—O4	140.5 (3)
C10—C11—C12—C7	2.6 (3)	C7—C8—O5—C25	−86.9 (3)
C10—C11—C12—N1	−176.9 (2)	C9—C8—O5—C25	99.3 (3)
C8—C7—C12—C11	0.1 (4)	C14—C15—O6—C27	6.6 (4)
C6—C7—C12—C11	−177.0 (2)	C16—C15—O6—C27	−173.2 (3)
C8—C7—C12—N1	179.7 (2)	C17—C16—O7—C28	−8.0 (4)
C6—C7—C12—N1	2.6 (3)	C15—C16—O7—C28	171.9 (3)
C11—C10—C13—C14	118.4 (3)	C12—N1—S1—O1	−167.4 (2)
C9—C10—C13—C14	−59.5 (3)	C1—N1—S1—O1	36.5 (3)
C11—C10—C13—C18	−57.2 (3)	C12—N1—S1—O2	−38.9 (2)
C9—C10—C13—C18	124.9 (3)	C1—N1—S1—O2	164.9 (2)
C18—C13—C14—C15	−0.7 (4)	C12—N1—S1—C19	76.5 (2)
C10—C13—C14—C15	−176.5 (2)	C1—N1—S1—C19	−79.7 (2)
C13—C14—C15—O6	−178.7 (2)	C20—C19—S1—O1	−24.5 (3)
C13—C14—C15—C16	1.1 (4)	C24—C19—S1—O1	157.3 (2)
O6—C15—C16—O7	−0.4 (3)	C20—C19—S1—O2	−157.6 (2)
C14—C15—C16—O7	179.8 (2)	C24—C19—S1—O2	24.2 (3)
O6—C15—C16—C17	179.5 (2)	C20—C19—S1—N1	89.1 (3)
C14—C15—C16—C17	−0.3 (4)	C24—C19—S1—N1	−89.1 (3)
O7—C16—C17—C18	178.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1	0.93	2.35	2.942 (5)	122
C11—H11···O2	0.93	2.32	2.927 (3)	122
C25—H25B···O8	0.96	2.60	3.194 (5)	120
C17—H17···O7i	0.93	2.56	3.384 (3)	148
C27—H27B···O3ii	0.96	2.56	3.239 (5)	128
C27—H27B···O8iii	0.96	2.58	2.943 (5)	103
C25—H25A···Cg1iv	0.96	2.97	3.675 (4)	131

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1	0.93	2.35	2.942 (5)	122
C11—H11⋯O2	0.93	2.32	2.927 (3)	122
C25—H25B⋯O8	0.96	2.60	3.194 (5)	120
C17—H17⋯O7i	0.93	2.56	3.384 (3)	148
C27—H27B⋯O3ii	0.96	2.56	3.239 (5)	128
C27—H27B⋯O8iii	0.96	2.58	2.943 (5)	103
C25—H25A⋯Cg1iv	0.96	2.97	3.675 (4)	131

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