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

In the title compound, C26H19BrN2O5S, the carbazole tricycle is essentially planar, with the largest deviation being 0.126 (3) Å for the C atom connected to the nitro-phenyl group. The carbazole moiety is almost orthogonal to the benzene rings of the adjacent phenyl-sulfonyl and nitro-phenyl groups, making dihedral angles of 85.43 (15) and 88.62 (12)°, respectively. The mol-ecular conformation is stabilized by two C-H⋯O hydrogen bonds involving the sulfone group, which form similar six-membered rings. In the crystal, mol-ecules symmetrically related by a glide plane are linked in C(6) chains parallel to [001] by C-H⋯O hydrogen bonds formed with the participation of the nitro group. The chains are reinforced by additional C-H⋯π inter-actions.

Related literature

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

Experimental

Crystal data

C26H19BrN2O5S

M = 551.40

Monoclinic,

a = 10.3176 (4) Å

b = 14.4431 (6) Å

c = 15.4901 (6) Å

β = 92.329 (2)°

V = 2306.40 (16) Å3

Z = 4

Mo Kα radiation

μ = 1.92 mm−1

T = 296 K

0.35 × 0.30 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.901, T max = 0.905

28756 measured reflections

6652 independent reflections

3939 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.161

S = 1.03

6652 reflections

317 parameters

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.74 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/S160053681401143X/ld2127sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681401143X/ld2127Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S160053681401143X/ld2127Isup3.cml

CCDC reference: 1003645

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

C26H19BrN2O5S	F(000) = 1120
Mr = 551.40	Dx = 1.588 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6652 reflections
a = 10.3176 (4) Å	θ = 2.0–27.0°
b = 14.4431 (6) Å	µ = 1.92 mm−1
c = 15.4901 (6) Å	T = 296 K
β = 92.329 (2)°	Block, white
V = 2306.40 (16) Å3	0.35 × 0.30 × 0.25 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	6652 independent reflections
Radiation source: fine-focus sealed tube	3939 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
ω &φ scans	θmax = 30.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −14→13
Tmin = 0.901, Tmax = 0.905	k = −20→19
28756 measured reflections	l = −17→21

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.161	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0816P)2 + 0.8074P] where P = (Fo2 + 2Fc2)/3
6652 reflections	(Δ/σ)max = 0.001
317 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.74 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	0.5239 (3)	0.9609 (2)	0.16131 (19)	0.0406 (6)
C2	0.4792 (3)	1.0177 (2)	0.2262 (2)	0.0545 (8)
H2	0.4971	1.0808	0.2272	0.065*
C3	0.4077 (3)	0.9774 (3)	0.2886 (2)	0.0624 (9)
H3	0.3769	1.0139	0.3328	0.075*
C4	0.3802 (3)	0.8829 (3)	0.2873 (2)	0.0597 (9)
H4	0.3326	0.8573	0.3310	0.072*
C5	0.4221 (3)	0.8274 (2)	0.2225 (2)	0.0488 (7)
H5	0.4023	0.7645	0.2214	0.059*
C6	0.4952 (3)	0.8669 (2)	0.15814 (19)	0.0393 (6)
C7	0.5591 (3)	0.82841 (18)	0.08476 (18)	0.0363 (6)
C8	0.6265 (3)	0.89955 (18)	0.04518 (18)	0.0368 (6)
C9	0.7036 (3)	0.88394 (19)	−0.02381 (18)	0.0396 (6)
H9	0.7454	0.9326	−0.0505	0.048*
C10	0.7173 (3)	0.79316 (19)	−0.05237 (18)	0.0366 (6)
C11	0.6474 (3)	0.72050 (18)	−0.01624 (17)	0.0370 (6)
C12	0.5667 (3)	0.73930 (18)	0.05171 (18)	0.0363 (6)
C13	0.3650 (3)	0.6679 (3)	0.0589 (2)	0.0654 (10)
H13A	0.3240	0.7248	0.0748	0.098*
H13B	0.3216	0.6168	0.0848	0.098*
H13C	0.3600	0.6614	−0.0028	0.098*
C14	0.8317 (3)	1.0435 (2)	0.1570 (2)	0.0443 (7)
C15	0.9401 (3)	1.0058 (2)	0.1228 (2)	0.0546 (8)
H15	0.9433	0.9957	0.0636	0.065*
C16	1.0440 (4)	0.9831 (3)	0.1767 (3)	0.0678 (10)
H16	1.1179	0.9574	0.1541	0.081*
C17	1.0389 (4)	0.9983 (3)	0.2642 (3)	0.0755 (12)
H17	1.1099	0.9838	0.3006	0.091*
C18	0.9288 (4)	1.0349 (4)	0.2979 (3)	0.0779 (12)
H18	0.9251	1.0441	0.3572	0.093*
C19	0.8250 (4)	1.0576 (3)	0.2448 (2)	0.0641 (10)
H19	0.7505	1.0824	0.2675	0.077*
C20	0.8034 (3)	0.77497 (18)	−0.12588 (17)	0.0372 (6)
C21	0.7515 (3)	0.7773 (2)	−0.2098 (2)	0.0536 (8)
H21	0.6637	0.7901	−0.2192	0.064*
C22	0.8278 (4)	0.7609 (3)	−0.2803 (2)	0.0641 (10)
H22	0.7906	0.7626	−0.3360	0.077*
C23	0.9561 (4)	0.7425 (3)	−0.2683 (2)	0.0633 (10)
H23	1.0071	0.7328	−0.3157	0.076*
C24	1.0099 (3)	0.7381 (2)	−0.1871 (2)	0.0531 (8)
H24	1.0975	0.7240	−0.1786	0.064*
C25	0.9345 (3)	0.75469 (19)	−0.11715 (17)	0.0386 (6)
C26	0.6569 (3)	0.6230 (2)	−0.0488 (2)	0.0472 (7)
H26A	0.6094	0.5762	−0.0237	0.057*
H26B	0.7103	0.6095	−0.0940	0.057*
N1	0.6006 (2)	0.98366 (15)	0.08997 (16)	0.0407 (5)
N2	1.0011 (3)	0.7494 (2)	−0.03198 (18)	0.0520 (7)
O1	0.9650 (3)	0.7991 (2)	0.02487 (15)	0.0771 (8)
O2	1.0921 (3)	0.6960 (2)	−0.0230 (2)	0.0881 (9)
O3	0.6318 (3)	1.14928 (15)	0.12702 (17)	0.0634 (6)
O4	0.7410 (3)	1.08277 (15)	0.00314 (15)	0.0575 (6)
O5	0.4979 (2)	0.66924 (14)	0.08849 (14)	0.0482 (5)
S1	0.69953 (8)	1.07490 (5)	0.08859 (5)	0.0460 (2)
Br1	0.80182 (4)	0.55845 (2)	0.01227 (2)	0.06233 (16)

	U11	U22	U33	U12	U13	U23
C1	0.0317 (14)	0.0433 (15)	0.0466 (16)	0.0042 (11)	0.0016 (12)	−0.0051 (13)
C2	0.0420 (18)	0.0529 (19)	0.069 (2)	0.0071 (14)	0.0026 (16)	−0.0164 (17)
C3	0.0446 (19)	0.082 (3)	0.061 (2)	0.0042 (18)	0.0081 (16)	−0.021 (2)
C4	0.0427 (18)	0.085 (3)	0.0519 (19)	−0.0037 (17)	0.0084 (15)	−0.0034 (18)
C5	0.0413 (17)	0.0549 (18)	0.0504 (18)	−0.0038 (14)	0.0027 (14)	−0.0001 (15)
C6	0.0295 (14)	0.0421 (15)	0.0459 (15)	0.0027 (11)	−0.0025 (12)	−0.0004 (12)
C7	0.0283 (13)	0.0367 (14)	0.0434 (15)	0.0008 (10)	−0.0047 (11)	0.0007 (12)
C8	0.0345 (14)	0.0303 (13)	0.0452 (15)	0.0016 (11)	−0.0042 (12)	−0.0011 (11)
C9	0.0397 (15)	0.0339 (14)	0.0453 (16)	−0.0051 (11)	0.0034 (13)	0.0009 (12)
C10	0.0313 (14)	0.0369 (14)	0.0412 (15)	−0.0007 (11)	−0.0038 (11)	−0.0035 (12)
C11	0.0383 (14)	0.0300 (13)	0.0421 (15)	0.0004 (11)	−0.0063 (12)	−0.0038 (11)
C12	0.0344 (14)	0.0313 (13)	0.0427 (15)	−0.0041 (10)	−0.0042 (12)	0.0032 (11)
C13	0.055 (2)	0.077 (2)	0.064 (2)	−0.0356 (19)	0.0000 (18)	−0.0043 (19)
C14	0.0468 (17)	0.0392 (15)	0.0472 (17)	−0.0111 (12)	0.0052 (14)	−0.0028 (13)
C15	0.059 (2)	0.056 (2)	0.0495 (18)	−0.0072 (16)	0.0124 (16)	−0.0026 (15)
C16	0.054 (2)	0.070 (2)	0.080 (3)	0.0002 (18)	0.0105 (19)	0.001 (2)
C17	0.061 (3)	0.088 (3)	0.077 (3)	−0.011 (2)	−0.013 (2)	0.008 (2)
C18	0.068 (3)	0.119 (4)	0.046 (2)	−0.010 (2)	0.0014 (19)	−0.003 (2)
C19	0.052 (2)	0.091 (3)	0.050 (2)	−0.0078 (18)	0.0075 (17)	−0.0119 (18)
C20	0.0411 (15)	0.0327 (13)	0.0376 (14)	−0.0031 (11)	−0.0020 (12)	−0.0027 (11)
C21	0.0506 (18)	0.0586 (19)	0.0505 (18)	−0.0020 (15)	−0.0117 (15)	−0.0032 (15)
C22	0.083 (3)	0.074 (2)	0.0340 (17)	−0.007 (2)	−0.0107 (17)	−0.0052 (16)
C23	0.078 (3)	0.071 (2)	0.0413 (18)	−0.0043 (19)	0.0129 (18)	−0.0095 (16)
C24	0.0504 (19)	0.058 (2)	0.0514 (19)	0.0013 (15)	0.0104 (15)	−0.0059 (15)
C25	0.0405 (15)	0.0413 (15)	0.0337 (14)	−0.0024 (12)	−0.0018 (12)	0.0004 (11)
C26	0.0557 (18)	0.0365 (15)	0.0492 (17)	−0.0043 (13)	0.0000 (14)	−0.0066 (13)
N1	0.0402 (13)	0.0304 (11)	0.0515 (14)	0.0017 (10)	0.0030 (11)	−0.0057 (10)
N2	0.0368 (14)	0.0698 (18)	0.0488 (16)	−0.0042 (13)	−0.0049 (12)	0.0064 (14)
O1	0.0648 (17)	0.127 (3)	0.0389 (13)	0.0121 (16)	−0.0058 (12)	−0.0149 (15)
O2	0.0648 (18)	0.109 (2)	0.088 (2)	0.0272 (17)	−0.0267 (16)	0.0025 (17)
O3	0.0786 (17)	0.0319 (11)	0.0798 (17)	0.0056 (11)	0.0028 (13)	−0.0074 (11)
O4	0.0847 (17)	0.0381 (11)	0.0497 (13)	−0.0083 (11)	0.0030 (12)	0.0064 (9)
O5	0.0499 (12)	0.0393 (11)	0.0554 (12)	−0.0096 (9)	0.0016 (10)	0.0074 (9)
S1	0.0590 (5)	0.0277 (3)	0.0511 (4)	−0.0022 (3)	0.0013 (4)	−0.0011 (3)
Br1	0.0740 (3)	0.0455 (2)	0.0674 (3)	0.01137 (16)	0.00214 (19)	0.00155 (15)

C1—C2	1.390 (4)	C14—S1	1.752 (3)
C1—C6	1.391 (4)	C15—C16	1.371 (5)
C1—N1	1.423 (4)	C15—H15	0.9300
C2—C3	1.369 (5)	C16—C17	1.376 (6)
C2—H2	0.9300	C16—H16	0.9300
C3—C4	1.394 (6)	C17—C18	1.374 (6)
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.368 (5)	C18—C19	1.365 (6)
C4—H4	0.9300	C18—H18	0.9300
C5—C6	1.397 (4)	C19—H19	0.9300
C5—H5	0.9300	C20—C25	1.385 (4)
C6—C7	1.448 (4)	C20—C21	1.386 (4)
C7—C12	1.389 (4)	C21—C22	1.393 (5)
C7—C8	1.396 (4)	C21—H21	0.9300
C8—C9	1.377 (4)	C22—C23	1.355 (5)
C8—N1	1.429 (4)	C22—H22	0.9300
C9—C10	1.393 (4)	C23—C24	1.355 (5)
C9—H9	0.9300	C23—H23	0.9300
C10—C11	1.402 (4)	C24—C25	1.381 (4)
C10—C20	1.496 (4)	C24—H24	0.9300
C11—C12	1.395 (4)	C25—N2	1.465 (4)
C11—C26	1.500 (4)	C26—Br1	1.971 (3)
C12—O5	1.373 (3)	C26—H26A	0.9300
C13—O5	1.428 (4)	C26—H26B	0.9300
C13—H13A	0.9600	N1—S1	1.668 (2)
C13—H13B	0.9600	N2—O1	1.207 (4)
C13—H13C	0.9600	N2—O2	1.218 (4)
C14—C15	1.370 (5)	O3—S1	1.425 (2)
C14—C19	1.379 (5)	O4—S1	1.412 (2)
C2—C1—C6	121.7 (3)	C15—C16—H16	120.0
C2—C1—N1	129.6 (3)	C17—C16—H16	120.0
C6—C1—N1	108.8 (2)	C18—C17—C16	120.1 (4)
C3—C2—C1	117.6 (3)	C18—C17—H17	120.0
C3—C2—H2	121.2	C16—C17—H17	120.0
C1—C2—H2	121.2	C19—C18—C17	120.2 (4)
C2—C3—C4	121.4 (3)	C19—C18—H18	119.9
C2—C3—H3	119.3	C17—C18—H18	119.9
C4—C3—H3	119.3	C18—C19—C14	119.3 (4)
C5—C4—C3	121.0 (3)	C18—C19—H19	120.3
C5—C4—H4	119.5	C14—C19—H19	120.3
C3—C4—H4	119.5	C25—C20—C21	115.8 (3)
C4—C5—C6	118.7 (3)	C25—C20—C10	124.8 (2)
C4—C5—H5	120.7	C21—C20—C10	119.4 (3)
C6—C5—H5	120.7	C20—C21—C22	121.5 (3)
C1—C6—C5	119.6 (3)	C20—C21—H21	119.3
C1—C6—C7	107.4 (2)	C22—C21—H21	119.3
C5—C6—C7	132.9 (3)	C23—C22—C21	120.4 (3)
C12—C7—C8	118.9 (3)	C23—C22—H22	119.8
C12—C7—C6	132.8 (3)	C21—C22—H22	119.8
C8—C7—C6	108.3 (2)	C22—C23—C24	119.8 (3)
C9—C8—C7	122.3 (3)	C22—C23—H23	120.1
C9—C8—N1	129.9 (3)	C24—C23—H23	120.1
C7—C8—N1	107.8 (2)	C23—C24—C25	119.9 (3)
C8—C9—C10	118.0 (3)	C23—C24—H24	120.1
C8—C9—H9	121.0	C25—C24—H24	120.1
C10—C9—H9	121.0	C24—C25—C20	122.6 (3)
C9—C10—C11	121.2 (3)	C24—C25—N2	116.0 (3)
C9—C10—C20	118.6 (2)	C20—C25—N2	121.3 (3)
C11—C10—C20	120.2 (2)	C11—C26—Br1	110.0 (2)
C12—C11—C10	119.2 (2)	C11—C26—H26A	120.0
C12—C11—C26	119.0 (3)	Br1—C26—H26A	81.8
C10—C11—C26	121.8 (3)	C11—C26—H26B	120.0
O5—C12—C7	119.5 (3)	Br1—C26—H26B	78.5
O5—C12—C11	120.3 (2)	H26A—C26—H26B	120.0
C7—C12—C11	120.2 (2)	C1—N1—C8	107.6 (2)
O5—C13—H13A	109.5	C1—N1—S1	123.50 (19)
O5—C13—H13B	109.5	C8—N1—S1	122.6 (2)
H13A—C13—H13B	109.5	O1—N2—O2	123.5 (3)
O5—C13—H13C	109.5	O1—N2—C25	118.6 (3)
H13A—C13—H13C	109.5	O2—N2—C25	117.9 (3)
H13B—C13—H13C	109.5	C12—O5—C13	112.5 (2)
C15—C14—C19	121.0 (3)	O4—S1—O3	120.22 (15)
C15—C14—S1	119.8 (2)	O4—S1—N1	106.54 (14)
C19—C14—S1	119.3 (3)	O3—S1—N1	106.23 (14)
C14—C15—C16	119.3 (3)	O4—S1—C14	109.25 (16)
C14—C15—H15	120.3	O3—S1—C14	108.98 (15)
C16—C15—H15	120.3	N1—S1—C14	104.43 (13)
C15—C16—C17	120.1 (4)
C6—C1—C2—C3	1.5 (5)	C9—C10—C20—C25	90.5 (4)
N1—C1—C2—C3	−179.1 (3)	C11—C10—C20—C25	−92.5 (3)
C1—C2—C3—C4	−0.3 (5)	C9—C10—C20—C21	−90.0 (3)
C2—C3—C4—C5	−1.0 (5)	C11—C10—C20—C21	87.0 (4)
C3—C4—C5—C6	1.0 (5)	C25—C20—C21—C22	−0.5 (5)
C2—C1—C6—C5	−1.5 (4)	C10—C20—C21—C22	179.9 (3)
N1—C1—C6—C5	179.0 (3)	C20—C21—C22—C23	−0.3 (6)
C2—C1—C6—C7	−178.4 (3)	C21—C22—C23—C24	1.3 (6)
N1—C1—C6—C7	2.0 (3)	C22—C23—C24—C25	−1.6 (6)
C4—C5—C6—C1	0.2 (4)	C23—C24—C25—C20	0.7 (5)
C4—C5—C6—C7	176.2 (3)	C23—C24—C25—N2	−179.4 (3)
C1—C6—C7—C12	178.5 (3)	C21—C20—C25—C24	0.3 (4)
C5—C6—C7—C12	2.1 (5)	C10—C20—C25—C24	179.8 (3)
C1—C6—C7—C8	0.6 (3)	C21—C20—C25—N2	−179.5 (3)
C5—C6—C7—C8	−175.8 (3)	C10—C20—C25—N2	0.0 (4)
C12—C7—C8—C9	−2.1 (4)	C12—C11—C26—Br1	−92.0 (3)
C6—C7—C8—C9	176.1 (3)	C10—C11—C26—Br1	88.1 (3)
C12—C7—C8—N1	178.8 (2)	C2—C1—N1—C8	176.7 (3)
C6—C7—C8—N1	−2.9 (3)	C6—C1—N1—C8	−3.9 (3)
C7—C8—C9—C10	−2.2 (4)	C2—C1—N1—S1	24.2 (4)
N1—C8—C9—C10	176.6 (3)	C6—C1—N1—S1	−156.4 (2)
C8—C9—C10—C11	4.5 (4)	C9—C8—N1—C1	−174.8 (3)
C8—C9—C10—C20	−178.5 (2)	C7—C8—N1—C1	4.2 (3)
C9—C10—C11—C12	−2.5 (4)	C9—C8—N1—S1	−22.0 (4)
C20—C10—C11—C12	−179.4 (2)	C7—C8—N1—S1	157.0 (2)
C9—C10—C11—C26	177.4 (3)	C24—C25—N2—O1	147.7 (3)
C20—C10—C11—C26	0.5 (4)	C20—C25—N2—O1	−32.5 (4)
C8—C7—C12—O5	−178.1 (2)	C24—C25—N2—O2	−30.9 (4)
C6—C7—C12—O5	4.2 (5)	C20—C25—N2—O2	148.9 (3)
C8—C7—C12—C11	4.2 (4)	C7—C12—O5—C13	81.0 (3)
C6—C7—C12—C11	−173.5 (3)	C11—C12—O5—C13	−101.3 (3)
C10—C11—C12—O5	−179.6 (2)	C1—N1—S1—O4	−170.5 (2)
C26—C11—C12—O5	0.5 (4)	C8—N1—S1—O4	41.0 (3)
C10—C11—C12—C7	−2.0 (4)	C1—N1—S1—O3	−41.2 (3)
C26—C11—C12—C7	178.1 (3)	C8—N1—S1—O3	170.3 (2)
C19—C14—C15—C16	−0.9 (5)	C1—N1—S1—C14	73.9 (2)
S1—C14—C15—C16	178.7 (3)	C8—N1—S1—C14	−74.6 (2)
C14—C15—C16—C17	−0.1 (6)	C15—C14—S1—O4	−18.4 (3)
C15—C16—C17—C18	1.1 (7)	C19—C14—S1—O4	161.3 (3)
C16—C17—C18—C19	−1.0 (7)	C15—C14—S1—O3	−151.5 (3)
C17—C18—C19—C14	0.0 (7)	C19—C14—S1—O3	28.1 (3)
C15—C14—C19—C18	0.9 (5)	C15—C14—S1—N1	95.3 (3)
S1—C14—C19—C18	−178.7 (3)	C19—C14—S1—N1	−85.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O3	0.93	2.34	2.941 (4)	122
C9—H9···O4	0.93	2.32	2.925 (4)	122
C23—H23···O1i	0.93	2.53	3.264 (4)	136
C22—H22···Cg1ii	0.93	2.95	3.810 (4)	155

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C7–C12 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O3	0.93	2.34	2.941 (4)	122
C9—H9⋯O4	0.93	2.32	2.925 (4)	122
C23—H23⋯O1i	0.93	2.53	3.264 (4)	136
C22—H22⋯Cg1ii	0.93	2.95	3.810 (4)	155

Symmetry codes: (i) ; (ii) .