4-(4-Meth-oxy-benzene-sulfonamido)-benzoic acid.

The asymmetric unit of the title compound, C(14)H(13)NO(5)S, contains two independent mol-ecules in which the dihedral angles between the aromatic rings are 83.45 (11) and 86.65 (9)°. In the crystal, the independent mol-ecules are connected by N-H⋯O and O-H⋯O hydrogen bonds, forming a double-chain structure along [401]. A weak π-π stacking inter-action with a centroid-centroid distance of 3.7509 (13) Å and C-H⋯O hydrogen bonds are also observed.

Related literature

For background to the biological activity of sulfonamides, see: Hanson et al. (1999 ▶). For related structures, see: Mustafa et al. (2010 ▶, 2011 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C14H13NO5S

M = 307.32

Monoclinic,

a = 8.6980 (3) Å

b = 21.7471 (8) Å

c = 14.5824 (6) Å

β = 95.153 (2)°

V = 2747.21 (18) Å3

Z = 8

Mo Kα radiation

μ = 0.26 mm−1

T = 296 K

0.38 × 0.31 × 0.28 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker 2007 ▶) T min = 0.909, T max = 0.931

25188 measured reflections

6806 independent reflections

5475 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.120

S = 1.04

6806 reflections

394 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.45 e Å−3

Δρmin = −0.30 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811025098/is2741sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811025098/is2741Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811025098/is2741Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C14H13NO5S	F(000) = 1280
Mr = 307.32	Dx = 1.486 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9988 reflections
a = 8.6980 (3) Å	θ = 2.4–28.4°
b = 21.7471 (8) Å	µ = 0.26 mm−1
c = 14.5824 (6) Å	T = 296 K
β = 95.153 (2)°	Block, light brown
V = 2747.21 (18) Å3	0.38 × 0.31 × 0.28 mm
Z = 8

Bruker APEXII CCD diffractometer	6806 independent reflections
Radiation source: sealed tube	5475 reflections with I > 2σ(I)
graphite	Rint = 0.018
φ and ω scans	θmax = 28.4°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker 2007)	h = −11→11
Tmin = 0.909, Tmax = 0.931	k = −24→28
25188 measured reflections	l = −14→19

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0499P)2 + 1.497P] where P = (Fo2 + 2Fc2)/3
6806 reflections	(Δ/σ)max = 0.001
394 parameters	Δρmax = 0.45 e Å−3
4 restraints	Δρmin = −0.30 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
S1	−0.24733 (5)	0.16859 (2)	0.57376 (4)	0.0419 (1)
O1	0.53350 (14)	0.11383 (6)	0.80744 (9)	0.0418 (4)
O2	0.57070 (16)	0.21434 (6)	0.79480 (13)	0.0606 (5)
O3	−0.36648 (15)	0.20947 (6)	0.53547 (12)	0.0562 (5)
O4	−0.28249 (17)	0.12512 (7)	0.64187 (11)	0.0564 (5)
O5	−0.0035 (3)	0.02617 (9)	0.27559 (14)	0.0870 (8)
N1	−0.11308 (18)	0.21531 (7)	0.61562 (13)	0.0469 (5)
C1	0.4873 (2)	0.16478 (8)	0.78203 (12)	0.0373 (5)
C2	0.33184 (19)	0.17603 (8)	0.73538 (12)	0.0349 (5)
C3	0.2252 (2)	0.12892 (8)	0.72183 (12)	0.0371 (5)
C4	0.0773 (2)	0.14010 (8)	0.68239 (13)	0.0407 (5)
C5	0.03454 (19)	0.19958 (8)	0.65561 (12)	0.0361 (5)
C6	0.1406 (2)	0.24698 (8)	0.66846 (13)	0.0417 (5)
C7	0.2870 (2)	0.23542 (9)	0.70806 (14)	0.0444 (6)
C8	−0.1707 (2)	0.12793 (8)	0.48507 (13)	0.0396 (5)
C9	−0.1128 (2)	0.15868 (9)	0.41275 (16)	0.0511 (7)
C10	−0.0545 (3)	0.12605 (11)	0.34123 (16)	0.0567 (7)
C11	−0.0575 (3)	0.06309 (11)	0.34217 (17)	0.0599 (8)
C12	−0.1172 (4)	0.03327 (11)	0.4127 (2)	0.0762 (10)
C13	−0.1732 (3)	0.06474 (10)	0.48410 (17)	0.0612 (8)
C14	0.0691 (3)	0.05350 (15)	0.20391 (19)	0.0827 (10)
S2	0.65408 (5)	0.38949 (2)	0.58411 (3)	0.0410 (1)
O6	−0.15326 (16)	0.40548 (7)	0.37226 (11)	0.0520 (5)
O7	−0.15559 (17)	0.30391 (7)	0.37416 (16)	0.0794 (7)
O8	0.79224 (15)	0.35378 (7)	0.60408 (11)	0.0537 (5)
O9	0.65854 (17)	0.44420 (7)	0.53070 (11)	0.0550 (5)
O10	0.3728 (2)	0.45077 (9)	0.92259 (12)	0.0764 (7)
N2	0.53708 (18)	0.34000 (7)	0.53111 (12)	0.0440 (5)
C15	−0.0880 (2)	0.35269 (9)	0.38936 (14)	0.0433 (5)
C16	0.07422 (19)	0.35329 (8)	0.42858 (12)	0.0369 (5)
C17	0.1530 (2)	0.40609 (8)	0.45785 (13)	0.0419 (5)
C18	0.3058 (2)	0.40391 (8)	0.49278 (14)	0.0435 (6)
C19	0.38196 (19)	0.34749 (8)	0.49887 (11)	0.0347 (5)
C20	0.3038 (2)	0.29444 (8)	0.46977 (13)	0.0395 (5)
C21	0.1526 (2)	0.29756 (8)	0.43499 (14)	0.0429 (5)
C22	0.57550 (19)	0.40798 (8)	0.68678 (13)	0.0375 (5)
C23	0.5632 (2)	0.36265 (8)	0.75171 (14)	0.0430 (5)
C24	0.4966 (2)	0.37489 (9)	0.83181 (14)	0.0468 (6)
C25	0.4431 (2)	0.43392 (10)	0.84718 (14)	0.0496 (6)
C26	0.4594 (3)	0.48007 (9)	0.78309 (15)	0.0513 (7)
C27	0.5238 (2)	0.46746 (8)	0.70259 (14)	0.0444 (6)
C28	0.3489 (4)	0.40625 (16)	0.9901 (2)	0.1000 (14)
HN1	−0.129 (3)	0.2526 (7)	0.6033 (15)	0.0500*
HO1	0.654 (2)	0.2050 (11)	0.8197 (16)	0.0630*
H3	0.25340	0.08910	0.73950	0.0450*
H4	0.00680	0.10800	0.67380	0.0490*
H6	0.11270	0.28670	0.65020	0.0500*
H7	0.35730	0.26760	0.71680	0.0530*
H9	−0.11280	0.20140	0.41180	0.0610*
H10	−0.01380	0.14690	0.29320	0.0680*
H12	−0.12010	−0.00950	0.41260	0.0910*
H13	−0.21280	0.04330	0.53190	0.0730*
H14A	−0.00400	0.07850	0.16740	0.1240*
H14B	0.10790	0.02210	0.16600	0.1240*
H14C	0.15310	0.07870	0.22920	0.1240*
HN2	0.571 (2)	0.3049 (8)	0.5344 (15)	0.0490*
HO2	−0.245 (2)	0.3998 (11)	0.3583 (17)	0.0610*
H17	0.10200	0.44370	0.45390	0.0500*
H18	0.35740	0.43970	0.51200	0.0520*
H20	0.35420	0.25670	0.47390	0.0470*
H21	0.10130	0.26170	0.41530	0.0520*
H23	0.60040	0.32340	0.74130	0.0520*
H24	0.48740	0.34410	0.87520	0.0560*
H26	0.42660	0.51980	0.79470	0.0620*
H27	0.53290	0.49820	0.65910	0.0530*
H28A	0.28250	0.37450	0.96350	0.1500*
H28B	0.30170	0.42530	1.04000	0.1500*
H28C	0.44620	0.38870	1.01290	0.1500*

	U11	U22	U33	U12	U13	U23
S1	0.0310 (2)	0.0358 (2)	0.0574 (3)	0.0010 (2)	−0.0046 (2)	−0.0053 (2)
O1	0.0374 (6)	0.0350 (6)	0.0519 (8)	0.0030 (5)	−0.0018 (5)	−0.0010 (5)
O2	0.0371 (7)	0.0354 (7)	0.1042 (13)	−0.0012 (6)	−0.0225 (8)	0.0033 (8)
O3	0.0364 (7)	0.0425 (7)	0.0860 (11)	0.0076 (6)	−0.0154 (7)	−0.0127 (7)
O4	0.0517 (8)	0.0546 (9)	0.0638 (9)	−0.0061 (7)	0.0110 (7)	0.0009 (7)
O5	0.1154 (16)	0.0666 (11)	0.0801 (13)	0.0167 (11)	0.0143 (12)	−0.0180 (10)
N1	0.0376 (8)	0.0318 (7)	0.0680 (11)	0.0034 (6)	−0.0133 (7)	−0.0069 (7)
C1	0.0345 (8)	0.0343 (8)	0.0424 (9)	0.0017 (7)	−0.0001 (7)	−0.0041 (7)
C2	0.0330 (8)	0.0352 (8)	0.0358 (8)	0.0011 (6)	−0.0003 (6)	−0.0031 (7)
C3	0.0395 (9)	0.0312 (8)	0.0399 (9)	0.0027 (7)	−0.0009 (7)	−0.0030 (7)
C4	0.0392 (9)	0.0318 (8)	0.0499 (10)	−0.0025 (7)	−0.0032 (7)	−0.0062 (7)
C5	0.0335 (8)	0.0373 (9)	0.0365 (8)	0.0020 (7)	−0.0022 (6)	−0.0059 (7)
C6	0.0423 (9)	0.0312 (8)	0.0500 (10)	0.0009 (7)	−0.0052 (8)	0.0028 (7)
C7	0.0391 (9)	0.0354 (9)	0.0568 (11)	−0.0057 (7)	−0.0061 (8)	0.0014 (8)
C8	0.0355 (8)	0.0331 (8)	0.0481 (10)	0.0000 (7)	−0.0082 (7)	−0.0018 (7)
C9	0.0476 (11)	0.0381 (10)	0.0661 (13)	−0.0008 (8)	−0.0028 (9)	0.0036 (9)
C10	0.0500 (11)	0.0632 (14)	0.0565 (13)	0.0019 (10)	0.0026 (9)	0.0046 (11)
C11	0.0631 (13)	0.0512 (12)	0.0633 (14)	0.0103 (10)	−0.0055 (11)	−0.0105 (11)
C12	0.112 (2)	0.0380 (12)	0.0800 (18)	0.0057 (13)	0.0163 (16)	−0.0088 (11)
C13	0.0842 (16)	0.0351 (10)	0.0653 (14)	0.0013 (10)	0.0117 (12)	0.0018 (10)
C14	0.0737 (17)	0.108 (2)	0.0657 (17)	0.0365 (17)	0.0026 (13)	−0.0108 (16)
S2	0.0325 (2)	0.0355 (2)	0.0537 (3)	−0.0009 (2)	−0.0035 (2)	−0.0059 (2)
O6	0.0353 (7)	0.0463 (8)	0.0725 (10)	0.0065 (6)	−0.0051 (6)	0.0095 (7)
O7	0.0405 (8)	0.0438 (8)	0.1466 (18)	−0.0054 (6)	−0.0317 (9)	0.0155 (10)
O8	0.0321 (6)	0.0509 (8)	0.0756 (10)	0.0035 (6)	−0.0081 (6)	−0.0153 (7)
O9	0.0607 (9)	0.0432 (8)	0.0621 (9)	−0.0048 (7)	0.0111 (7)	0.0019 (7)
O10	0.1012 (14)	0.0737 (11)	0.0574 (10)	0.0305 (10)	0.0240 (9)	0.0128 (9)
N2	0.0356 (8)	0.0331 (8)	0.0602 (10)	0.0064 (6)	−0.0130 (7)	−0.0107 (7)
C15	0.0335 (8)	0.0392 (9)	0.0564 (11)	0.0020 (7)	−0.0007 (8)	0.0085 (8)
C16	0.0310 (8)	0.0389 (9)	0.0403 (9)	0.0020 (7)	0.0004 (7)	0.0061 (7)
C17	0.0392 (9)	0.0365 (9)	0.0489 (10)	0.0081 (7)	−0.0027 (8)	−0.0012 (8)
C18	0.0419 (9)	0.0331 (9)	0.0532 (11)	0.0028 (7)	−0.0077 (8)	−0.0069 (8)
C19	0.0319 (8)	0.0375 (9)	0.0338 (8)	0.0014 (6)	−0.0020 (6)	−0.0020 (7)
C20	0.0347 (8)	0.0300 (8)	0.0527 (10)	0.0043 (6)	−0.0024 (7)	0.0009 (7)
C21	0.0345 (8)	0.0345 (9)	0.0583 (11)	−0.0032 (7)	−0.0043 (8)	0.0023 (8)
C22	0.0338 (8)	0.0303 (8)	0.0464 (10)	−0.0015 (6)	−0.0078 (7)	−0.0021 (7)
C23	0.0412 (9)	0.0286 (8)	0.0571 (11)	0.0022 (7)	−0.0072 (8)	0.0017 (8)
C24	0.0454 (10)	0.0399 (10)	0.0534 (11)	0.0013 (8)	−0.0046 (8)	0.0109 (8)
C25	0.0498 (11)	0.0488 (11)	0.0490 (11)	0.0076 (9)	−0.0020 (9)	0.0021 (9)
C26	0.0661 (13)	0.0323 (9)	0.0548 (12)	0.0104 (9)	0.0021 (10)	−0.0009 (8)
C27	0.0541 (11)	0.0288 (8)	0.0494 (11)	0.0010 (7)	−0.0010 (8)	0.0017 (7)
C28	0.110 (2)	0.119 (3)	0.0770 (19)	0.058 (2)	0.0408 (18)	0.0445 (19)

S1—O3	1.4395 (15)	C3—H3	0.9300
S1—O4	1.4242 (16)	C4—H4	0.9300
S1—N1	1.6249 (17)	C6—H6	0.9300
S1—C8	1.7475 (19)	C7—H7	0.9300
S2—O8	1.4385 (15)	C9—H9	0.9300
S2—O9	1.4245 (16)	C10—H10	0.9300
S2—N2	1.6279 (17)	C12—H12	0.9300
S2—C22	1.7476 (19)	C13—H13	0.9300
O1—C1	1.225 (2)	C14—H14A	0.9600
O2—C1	1.303 (2)	C14—H14B	0.9600
O5—C11	1.375 (3)	C14—H14C	0.9600
O5—C14	1.401 (4)	C15—C16	1.474 (2)
O2—HO1	0.807 (19)	C16—C21	1.390 (2)
O6—C15	1.295 (2)	C16—C17	1.385 (2)
O7—C15	1.223 (2)	C17—C18	1.381 (3)
O10—C25	1.356 (3)	C18—C19	1.393 (2)
O10—C28	1.409 (4)	C19—C20	1.386 (2)
O6—HO2	0.815 (18)	C20—C21	1.368 (3)
N1—C5	1.404 (2)	C22—C27	1.395 (2)
N1—HN1	0.839 (16)	C22—C23	1.378 (3)
N2—C19	1.398 (2)	C23—C24	1.376 (3)
N2—HN2	0.818 (18)	C24—C25	1.391 (3)
C1—C2	1.478 (2)	C25—C26	1.387 (3)
C2—C7	1.397 (3)	C26—C27	1.373 (3)
C2—C3	1.384 (2)	C17—H17	0.9300
C3—C4	1.383 (2)	C18—H18	0.9300
C4—C5	1.392 (2)	C20—H20	0.9300
C5—C6	1.385 (2)	C21—H21	0.9300
C6—C7	1.373 (3)	C23—H23	0.9300
C8—C9	1.382 (3)	C24—H24	0.9300
C8—C13	1.374 (3)	C26—H26	0.9300
C9—C10	1.394 (3)	C27—H27	0.9300
C10—C11	1.370 (3)	C28—H28A	0.9600
C11—C12	1.358 (4)	C28—H28B	0.9600
C12—C13	1.371 (4)	C28—H28C	0.9600
O3—S1—O4	119.23 (9)	C11—C10—H10	120.00
O3—S1—N1	103.16 (8)	C11—C12—H12	119.00
O3—S1—C8	109.55 (10)	C13—C12—H12	119.00
O4—S1—N1	110.19 (10)	C12—C13—H13	120.00
O4—S1—C8	107.48 (9)	C8—C13—H13	120.00
N1—S1—C8	106.58 (9)	H14A—C14—H14C	109.00
O9—S2—N2	109.83 (9)	H14B—C14—H14C	109.00
O9—S2—C22	107.95 (9)	O5—C14—H14A	109.00
N2—S2—C22	106.44 (8)	H14A—C14—H14B	109.00
O8—S2—C22	109.55 (9)	O5—C14—H14B	109.00
O8—S2—O9	119.89 (9)	O5—C14—H14C	110.00
O8—S2—N2	102.38 (8)	O6—C15—O7	122.59 (17)
C11—O5—C14	119.0 (2)	O6—C15—C16	117.04 (16)
C1—O2—HO1	108.8 (17)	O7—C15—C16	120.37 (17)
C25—O10—C28	119.1 (2)	C15—C16—C21	117.72 (16)
C15—O6—HO2	108.4 (17)	C15—C16—C17	123.83 (16)
S1—N1—C5	127.10 (13)	C17—C16—C21	118.44 (16)
C5—N1—HN1	116.8 (17)	C16—C17—C18	121.23 (16)
S1—N1—HN1	115.1 (17)	C17—C18—C19	119.35 (16)
S2—N2—C19	128.76 (13)	C18—C19—C20	119.74 (16)
C19—N2—HN2	117.4 (13)	N2—C19—C18	124.27 (16)
S2—N2—HN2	112.5 (13)	N2—C19—C20	115.98 (15)
O1—C1—O2	122.80 (16)	C19—C20—C21	120.06 (16)
O1—C1—C2	123.41 (16)	C16—C21—C20	121.18 (16)
O2—C1—C2	113.78 (15)	S2—C22—C23	118.99 (14)
C3—C2—C7	118.51 (16)	S2—C22—C27	120.76 (14)
C1—C2—C7	120.31 (16)	C23—C22—C27	120.24 (17)
C1—C2—C3	121.11 (16)	C22—C23—C24	120.65 (17)
C2—C3—C4	121.04 (16)	C23—C24—C25	119.21 (18)
C3—C4—C5	119.68 (16)	O10—C25—C26	115.58 (19)
N1—C5—C6	116.62 (15)	O10—C25—C24	124.20 (19)
N1—C5—C4	123.66 (16)	C24—C25—C26	120.22 (19)
C4—C5—C6	119.72 (16)	C25—C26—C27	120.38 (18)
C5—C6—C7	120.13 (17)	C22—C27—C26	119.25 (18)
C2—C7—C6	120.92 (17)	C16—C17—H17	119.00
C9—C8—C13	118.86 (19)	C18—C17—H17	119.00
S1—C8—C13	120.45 (16)	C17—C18—H18	120.00
S1—C8—C9	120.63 (14)	C19—C18—H18	120.00
C8—C9—C10	120.45 (19)	C19—C20—H20	120.00
C9—C10—C11	119.5 (2)	C21—C20—H20	120.00
O5—C11—C10	124.7 (2)	C16—C21—H21	119.00
C10—C11—C12	119.6 (2)	C20—C21—H21	119.00
O5—C11—C12	115.7 (2)	C22—C23—H23	120.00
C11—C12—C13	121.5 (2)	C24—C23—H23	120.00
C8—C13—C12	120.0 (2)	C23—C24—H24	120.00
C4—C3—H3	119.00	C25—C24—H24	120.00
C2—C3—H3	120.00	C25—C26—H26	120.00
C3—C4—H4	120.00	C27—C26—H26	120.00
C5—C4—H4	120.00	C22—C27—H27	120.00
C7—C6—H6	120.00	C26—C27—H27	120.00
C5—C6—H6	120.00	O10—C28—H28A	109.00
C2—C7—H7	120.00	O10—C28—H28B	109.00
C6—C7—H7	120.00	O10—C28—H28C	110.00
C10—C9—H9	120.00	H28A—C28—H28B	110.00
C8—C9—H9	120.00	H28A—C28—H28C	109.00
C9—C10—H10	120.00	H28B—C28—H28C	109.00
O3—S1—N1—C5	−175.24 (17)	N1—C5—C6—C7	179.32 (18)
O4—S1—N1—C5	56.43 (19)	C4—C5—C6—C7	−0.5 (3)
C8—S1—N1—C5	−59.89 (19)	C5—C6—C7—C2	0.4 (3)
N1—S1—C8—C9	−56.08 (18)	S1—C8—C9—C10	−178.76 (17)
O3—S1—C8—C9	54.89 (17)	C13—C8—C9—C10	−1.6 (3)
O4—S1—C8—C9	−174.20 (15)	S1—C8—C13—C12	178.0 (2)
N1—S1—C8—C13	126.77 (18)	C9—C8—C13—C12	0.7 (4)
O3—S1—C8—C13	−122.27 (18)	C8—C9—C10—C11	1.2 (3)
O4—S1—C8—C13	8.7 (2)	C9—C10—C11—O5	180.0 (2)
O8—S2—C22—C23	−46.00 (17)	C9—C10—C11—C12	0.0 (4)
O8—S2—C22—C27	134.90 (15)	C10—C11—C12—C13	−0.8 (5)
O9—S2—C22—C23	−178.14 (14)	O5—C11—C12—C13	179.2 (3)
N2—S2—C22—C23	64.00 (16)	C11—C12—C13—C8	0.5 (4)
C22—S2—N2—C19	61.60 (18)	O7—C15—C16—C17	−172.0 (2)
O9—S2—C22—C27	2.76 (17)	O6—C15—C16—C17	8.0 (3)
N2—S2—C22—C27	−115.10 (15)	O6—C15—C16—C21	−170.94 (18)
O9—S2—N2—C19	−55.01 (19)	O7—C15—C16—C21	9.0 (3)
O8—S2—N2—C19	176.56 (16)	C21—C16—C17—C18	−0.1 (3)
C14—O5—C11—C10	4.3 (4)	C17—C16—C21—C20	0.4 (3)
C14—O5—C11—C12	−175.8 (3)	C15—C16—C17—C18	−179.01 (18)
C28—O10—C25—C24	−1.0 (3)	C15—C16—C21—C20	179.36 (18)
C28—O10—C25—C26	178.7 (2)	C16—C17—C18—C19	−0.2 (3)
S1—N1—C5—C4	−13.7 (3)	C17—C18—C19—C20	0.1 (3)
S1—N1—C5—C6	166.56 (15)	C17—C18—C19—N2	178.53 (17)
S2—N2—C19—C20	−169.78 (14)	N2—C19—C20—C21	−178.38 (17)
S2—N2—C19—C18	11.7 (3)	C18—C19—C20—C21	0.2 (3)
O1—C1—C2—C7	−179.84 (17)	C19—C20—C21—C16	−0.4 (3)
O2—C1—C2—C3	−175.85 (17)	S2—C22—C27—C26	178.50 (16)
O2—C1—C2—C7	1.0 (3)	C23—C22—C27—C26	−0.6 (3)
O1—C1—C2—C3	3.4 (3)	S2—C22—C23—C24	−177.51 (14)
C3—C2—C7—C6	−0.1 (3)	C27—C22—C23—C24	1.6 (3)
C1—C2—C3—C4	176.70 (17)	C22—C23—C24—C25	−0.7 (3)
C7—C2—C3—C4	−0.2 (3)	C23—C24—C25—C26	−1.1 (3)
C1—C2—C7—C6	−177.01 (17)	C23—C24—C25—O10	178.56 (18)
C2—C3—C4—C5	0.1 (3)	O10—C25—C26—C27	−177.6 (2)
C3—C4—C5—C6	0.2 (3)	C24—C25—C26—C27	2.2 (3)
C3—C4—C5—N1	−179.58 (17)	C25—C26—C27—C22	−1.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—HN1···O8i	0.84 (2)	2.31 (2)	3.122 (2)	165 (2)
O2—HO1···O7ii	0.81 (2)	1.78 (2)	2.583 (2)	172 (2)
N2—HN2···O3iii	0.82 (2)	2.15 (2)	2.959 (2)	173.(2)
O6—HO2···O1iv	0.82 (2)	2.02 (2)	2.8338 (19)	173 (2)
C4—H4···O4	0.93	2.54	3.149 (2)	123
C7—H7···O2	0.93	2.39	2.709 (2)	100
C9—H9···O7	0.93	2.32	3.224 (3)	165
C13—H13···O4	0.93	2.51	2.883 (3)	105
C13—H13···O10v	0.93	2.57	3.381 (3)	146
C14—H14A···O8iv	0.96	2.42	3.370 (3)	169
C23—H23···O2	0.93	2.52	3.286 (2)	140
C26—H26···O1vi	0.93	2.57	3.197 (2)	125
C27—H27···O9	0.93	2.54	2.905 (3)	104

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—HN1⋯O8i	0.84 (2)	2.31 (2)	3.122 (2)	165 (2)
O2—HO1⋯O7ii	0.81 (2)	1.78 (2)	2.583 (2)	172 (2)
N2—HN2⋯O3iii	0.82 (2)	2.15 (2)	2.959 (2)	173 (2)
O6—HO2⋯O1iv	0.82 (2)	2.02 (2)	2.8338 (19)	173 (2)
C4—H4⋯O4	0.93	2.54	3.149 (2)	123
C9—H9⋯O7	0.93	2.32	3.224 (3)	165
C13—H13⋯O10v	0.93	2.57	3.381 (3)	146
C14—H14A⋯O8iv	0.96	2.42	3.370 (3)	169
C23—H23⋯O2	0.93	2.52	3.286 (2)	140
C26—H26⋯O1vi	0.93	2.57	3.197 (2)	125

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