N-[(2-Chloro-phen-yl)sulfon-yl]-2-meth-oxy-benzamide.

The title compound, C14H12ClNO4S, crystallizes with two mol-ecules in the asymmetric unit. The dihedral angles between the benzene rings are 89.68 (1) (mol-ecule 1) and 82.9 (1)° (mol-ecule 2). In each mol-ecule, intra-molecular N-H⋯O hydrogen bonds between the amide H atom and the meth-oxy O atom generate S(6) loops. In the crystal, mol-ecule 2 is linked into inversion dimers through pairs of C-H⋯O inter-actions, forming an R 2 (2)(8) ring motif. Mol-ecules 1 and 2 are further linked along the b-axis direction through C-H⋯π inter-actions. The crystal structure is further stabilized by several π-π stacking inter-actions [centroid-centroid separations = 3.7793 (1), 3.6697 (1) and 3.6958 (1) Å], thus generating a three-dimensional architecture.

Related literature

For similar structures, see: Gowda et al. (2010 ▶); Suchetan et al. (2010a ▶,b ▶, 2013 ▶). For n class="Chemical">hydrogen-bond motifs see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C14H12ClNO4S

M = 325.76

Triclinic,

a = 8.0508 (3) Å

b = 12.9487 (4) Å

c = 14.1915 (5) Å

α = 83.897 (2)°

β = 89.368 (2)°

γ = 89.704 (2)°

V = 1470.94 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.42 mm−1

T = 293 K

0.36 × 0.29 × 0.23 mm

Data collection

Bruker APEXII CCD diffractometer

34023 measured reflections

9760 independent reflections

6518 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.163

S = 0.90

9760 reflections

389 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.68 e Å−3

Δρmin = −0.59 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: n class="Gene">APEX2 and SAINT-Plus (Bruker, 2009 ▶); data reduction: SAINT-Plus and XPREP (Bruker, 2009 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536813029012/sj5359sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813029012/sj5359Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813029012/sj5359Isup3.cml

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

C14H12ClNO4S	F(000) = 672
Mr = 325.76	Prism
Triclinic, P1	Dx = 1.471 Mg m−3
Hall symbol: -P 1	Melting point: 429 K
a = 8.0508 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.9487 (4) Å	Cell parameters from 1234 reflections
c = 14.1915 (5) Å	θ = 1.6–31.8°
α = 83.897 (2)°	µ = 0.42 mm−1
β = 89.368 (2)°	T = 293 K
γ = 89.704 (2)°	Prism, colourless
V = 1470.94 (9) Å3	0.36 × 0.29 × 0.23 mm
Z = 4

Bruker APEXII CCD diffractometer	6518 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.028
Graphite monochromator	θmax = 31.8°, θmin = 1.6°
φ and ω scans	h = −11→11
34023 measured reflections	k = −17→19
9760 independent reflections	l = −20→20

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.163	H atoms treated by a mixture of independent and constrained refinement
S = 0.90	w = 1/[σ2(Fo2) + (0.0876P)2 + 0.587P] where P = (Fo2 + 2Fc2)/3
9760 reflections	(Δ/σ)max = 0.002
389 parameters	Δρmax = 0.68 e Å−3
0 restraints	Δρmin = −0.59 e Å−3

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 > 2σ(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
C28	−0.6577 (5)	1.3256 (3)	0.3153 (3)	0.1291 (16)
H28A	−0.6248	1.2553	0.3352	0.194*
H28B	−0.6856	1.3319	0.2494	0.194*
H28C	−0.7526	1.3435	0.3519	0.194*
HN2	−0.408 (3)	1.5138 (18)	0.2590 (15)	0.057 (6)*
HN1	0.080 (3)	1.0299 (18)	0.2691 (15)	0.056 (6)*
C1	0.4099 (2)	1.01693 (13)	0.14113 (11)	0.0413 (3)
C2	0.3854 (3)	1.11730 (15)	0.09867 (13)	0.0526 (4)
C3	0.5167 (3)	1.17506 (18)	0.05849 (16)	0.0692 (6)
H3	0.4993	1.2427	0.0311	0.083*
C4	0.6705 (4)	1.1329 (2)	0.05921 (16)	0.0732 (7)
H4	0.7584	1.1720	0.0317	0.088*
C5	0.7001 (3)	1.0329 (2)	0.09992 (17)	0.0696 (7)
H5	0.8066	1.0047	0.0995	0.084*
C6	0.5675 (2)	0.97436 (17)	0.14195 (14)	0.0533 (4)
H6	0.5857	0.9072	0.1702	0.064*
C7	0.2633 (3)	1.02032 (16)	0.35657 (13)	0.0504 (4)
C8	0.1764 (2)	1.07678 (14)	0.42977 (12)	0.0476 (4)
C9	0.0234 (3)	1.12861 (14)	0.41869 (13)	0.0520 (4)
C10	−0.0391 (3)	1.18159 (17)	0.49168 (16)	0.0654 (6)
H10	−0.1393	1.2174	0.4840	0.078*
C11	0.0456 (3)	1.18137 (18)	0.57482 (17)	0.0701 (6)
H11	0.0022	1.2170	0.6231	0.084*
C12	0.1934 (3)	1.1294 (2)	0.58768 (16)	0.0699 (6)
H12	0.2495	1.1285	0.6447	0.084*
C13	0.2585 (3)	1.07799 (18)	0.51452 (14)	0.0593 (5)
H13	0.3598	1.0436	0.5228	0.071*
C14	−0.2212 (4)	1.1690 (3)	0.3257 (2)	0.0902 (9)
H14A	−0.2893	1.1400	0.3777	0.135*
H14B	−0.2682	1.1528	0.2671	0.135*
H14C	−0.2159	1.2430	0.3260	0.135*
C15	−0.0676 (2)	1.58600 (13)	0.15496 (11)	0.0407 (3)
C16	−0.0377 (3)	1.48635 (14)	0.13150 (13)	0.0529 (4)
C17	0.1220 (3)	1.45853 (18)	0.10457 (17)	0.0687 (6)
H17	0.1427	1.3924	0.0872	0.082*
C18	0.2491 (3)	1.5294 (2)	0.10383 (17)	0.0691 (6)
H18	0.3555	1.5105	0.0859	0.083*
C19	0.2212 (3)	1.62651 (19)	0.12890 (15)	0.0601 (5)
H19	0.3083	1.6733	0.1291	0.072*
C20	0.0624 (2)	1.65527 (15)	0.15405 (13)	0.0485 (4)
H20	0.0429	1.7219	0.1705	0.058*
C21	−0.2474 (2)	1.53203 (16)	0.35569 (13)	0.0500 (4)
C22	−0.3193 (2)	1.45265 (15)	0.42864 (12)	0.0483 (4)
C23	−0.4520 (3)	1.38669 (16)	0.41651 (13)	0.0527 (4)
C24	−0.5045 (3)	1.31545 (18)	0.49100 (16)	0.0670 (6)
H24	−0.5931	1.2716	0.4825	0.080*
C25	−0.4266 (3)	1.3094 (2)	0.57675 (16)	0.0727 (7)
H25	−0.4626	1.2614	0.6260	0.087*
C26	−0.2968 (3)	1.3730 (2)	0.59061 (15)	0.0703 (7)
H26	−0.2450	1.3690	0.6492	0.084*
C27	−0.2425 (3)	1.44394 (18)	0.51671 (14)	0.0600 (5)
H27	−0.1529	1.4866	0.5261	0.072*
N1	0.1728 (2)	1.00103 (13)	0.27880 (11)	0.0495 (4)
N2	−0.3337 (2)	1.55288 (14)	0.27293 (11)	0.0526 (4)
O1	0.11150 (18)	0.93899 (12)	0.12765 (10)	0.0612 (4)
O2	0.3149 (2)	0.84221 (11)	0.22865 (11)	0.0659 (4)
O3	0.4060 (2)	0.99214 (16)	0.36392 (12)	0.0797 (5)
O4	−0.0573 (2)	1.12592 (13)	0.33491 (10)	0.0666 (4)
O5	−0.37606 (18)	1.61675 (14)	0.10764 (11)	0.0721 (5)
O6	−0.2480 (2)	1.73358 (11)	0.21074 (12)	0.0707 (4)
O7	−0.1198 (2)	1.57723 (14)	0.36765 (11)	0.0716 (4)
O8	−0.5245 (2)	1.39365 (13)	0.32949 (11)	0.0713 (5)
S1	0.24534 (6)	0.93882 (3)	0.19164 (3)	0.04506 (12)
S2	−0.26639 (6)	1.63258 (4)	0.18268 (3)	0.04893 (13)
Cl1	0.19015 (10)	1.17448 (5)	0.09374 (6)	0.0900 (2)
Cl2	−0.19141 (10)	1.39327 (5)	0.13476 (5)	0.0854 (2)

	U11	U22	U33	U12	U13	U23
C28	0.132 (3)	0.133 (3)	0.112 (2)	−0.091 (3)	−0.049 (2)	0.042 (2)
C1	0.0459 (9)	0.0403 (8)	0.0384 (8)	−0.0003 (7)	0.0031 (7)	−0.0087 (6)
C2	0.0644 (12)	0.0439 (9)	0.0494 (10)	−0.0006 (9)	0.0024 (9)	−0.0045 (7)
C3	0.0948 (18)	0.0555 (12)	0.0565 (12)	−0.0177 (12)	0.0091 (12)	−0.0021 (9)
C4	0.0816 (17)	0.0851 (17)	0.0549 (12)	−0.0299 (14)	0.0139 (11)	−0.0172 (11)
C5	0.0465 (11)	0.105 (2)	0.0630 (13)	−0.0006 (12)	0.0042 (10)	−0.0339 (13)
C6	0.0512 (11)	0.0604 (12)	0.0502 (10)	0.0086 (9)	−0.0004 (8)	−0.0147 (8)
C7	0.0534 (11)	0.0536 (10)	0.0443 (9)	−0.0040 (8)	0.0056 (8)	−0.0057 (7)
C8	0.0552 (11)	0.0433 (9)	0.0447 (9)	−0.0114 (8)	0.0098 (8)	−0.0071 (7)
C9	0.0661 (12)	0.0423 (9)	0.0476 (9)	−0.0038 (8)	0.0121 (9)	−0.0061 (7)
C10	0.0828 (16)	0.0524 (12)	0.0623 (12)	0.0013 (11)	0.0169 (11)	−0.0141 (9)
C11	0.0926 (18)	0.0607 (13)	0.0605 (12)	−0.0164 (13)	0.0222 (12)	−0.0239 (10)
C12	0.0870 (17)	0.0763 (15)	0.0491 (11)	−0.0278 (13)	0.0061 (11)	−0.0179 (10)
C13	0.0635 (13)	0.0647 (13)	0.0506 (10)	−0.0142 (10)	0.0051 (9)	−0.0105 (9)
C14	0.0921 (19)	0.103 (2)	0.0768 (16)	0.0482 (17)	−0.0087 (14)	−0.0173 (15)
C15	0.0437 (9)	0.0381 (8)	0.0395 (8)	−0.0020 (7)	0.0014 (6)	−0.0001 (6)
C16	0.0707 (13)	0.0398 (9)	0.0477 (9)	−0.0062 (9)	−0.0028 (9)	−0.0021 (7)
C17	0.0887 (17)	0.0498 (12)	0.0686 (13)	0.0219 (12)	−0.0008 (12)	−0.0119 (10)
C18	0.0566 (13)	0.0793 (16)	0.0706 (14)	0.0147 (12)	0.0058 (11)	−0.0057 (12)
C19	0.0480 (11)	0.0692 (14)	0.0620 (12)	−0.0037 (10)	0.0064 (9)	−0.0027 (10)
C20	0.0475 (10)	0.0454 (9)	0.0525 (10)	−0.0065 (8)	0.0059 (8)	−0.0049 (7)
C21	0.0490 (10)	0.0550 (11)	0.0457 (9)	−0.0053 (8)	0.0039 (8)	−0.0046 (8)
C22	0.0474 (10)	0.0529 (10)	0.0431 (9)	0.0055 (8)	0.0058 (7)	0.0007 (7)
C23	0.0539 (11)	0.0528 (10)	0.0489 (10)	0.0000 (9)	0.0040 (8)	0.0058 (8)
C24	0.0699 (14)	0.0591 (12)	0.0669 (13)	−0.0036 (10)	0.0124 (11)	0.0152 (10)
C25	0.0782 (16)	0.0750 (15)	0.0577 (12)	0.0167 (13)	0.0154 (11)	0.0230 (11)
C26	0.0752 (15)	0.0866 (17)	0.0457 (10)	0.0259 (13)	0.0012 (10)	0.0070 (10)
C27	0.0569 (12)	0.0752 (14)	0.0471 (10)	0.0115 (10)	−0.0006 (9)	−0.0029 (9)
N1	0.0474 (9)	0.0572 (10)	0.0453 (8)	0.0030 (8)	0.0056 (7)	−0.0122 (7)
N2	0.0454 (9)	0.0626 (10)	0.0471 (8)	−0.0139 (8)	0.0024 (7)	0.0072 (7)
O1	0.0529 (8)	0.0724 (10)	0.0619 (8)	−0.0076 (7)	0.0000 (7)	−0.0233 (7)
O2	0.0877 (11)	0.0367 (7)	0.0720 (9)	0.0038 (7)	0.0076 (8)	0.0002 (6)
O3	0.0606 (10)	0.1193 (15)	0.0633 (9)	0.0189 (10)	−0.0076 (8)	−0.0295 (9)
O4	0.0737 (10)	0.0727 (10)	0.0544 (8)	0.0239 (8)	0.0005 (7)	−0.0131 (7)
O5	0.0499 (8)	0.0969 (12)	0.0621 (9)	−0.0079 (8)	−0.0072 (7)	0.0262 (8)
O6	0.0714 (10)	0.0454 (8)	0.0932 (11)	0.0081 (7)	0.0246 (9)	−0.0007 (7)
O7	0.0663 (10)	0.0863 (11)	0.0612 (9)	−0.0286 (9)	−0.0060 (7)	−0.0011 (8)
O8	0.0776 (11)	0.0732 (10)	0.0592 (8)	−0.0338 (8)	−0.0117 (7)	0.0142 (7)
S1	0.0499 (3)	0.0389 (2)	0.0469 (2)	−0.00208 (18)	0.00520 (18)	−0.00783 (16)
S2	0.0410 (2)	0.0494 (3)	0.0531 (2)	−0.00109 (18)	0.00462 (18)	0.00939 (18)
Cl1	0.0898 (5)	0.0554 (3)	0.1200 (6)	0.0259 (3)	−0.0007 (4)	0.0116 (3)
Cl2	0.1187 (6)	0.0528 (3)	0.0861 (4)	−0.0362 (3)	0.0009 (4)	−0.0118 (3)

C28—O8	1.421 (3)	C15—C20	1.381 (2)
C28—H28A	0.9600	C15—C16	1.386 (3)
C28—H28B	0.9600	C15—S2	1.7626 (18)
C28—H28C	0.9600	C16—C17	1.394 (3)
C1—C6	1.381 (3)	C16—Cl2	1.729 (2)
C1—C2	1.387 (3)	C17—C18	1.377 (4)
C1—S1	1.7692 (18)	C17—H17	0.9300
C2—C3	1.381 (3)	C18—C19	1.360 (3)
C2—Cl1	1.733 (2)	C18—H18	0.9300
C3—C4	1.350 (4)	C19—C20	1.383 (3)
C3—H3	0.9300	C19—H19	0.9300
C4—C5	1.381 (4)	C20—H20	0.9300
C4—H4	0.9300	C21—O7	1.208 (2)
C5—C6	1.403 (3)	C21—N2	1.372 (2)
C5—H5	0.9300	C21—C22	1.493 (3)
C6—H6	0.9300	C22—C27	1.394 (3)
C7—O3	1.206 (2)	C22—C23	1.394 (3)
C7—N1	1.375 (3)	C23—O8	1.366 (2)
C7—C8	1.498 (3)	C23—C24	1.391 (3)
C8—C13	1.380 (3)	C24—C25	1.370 (3)
C8—C9	1.402 (3)	C24—H24	0.9300
C9—O4	1.365 (2)	C25—C26	1.363 (4)
C9—C10	1.390 (3)	C25—H25	0.9300
C10—C11	1.369 (3)	C26—C27	1.387 (3)
C10—H10	0.9300	C26—H26	0.9300
C11—C12	1.368 (4)	C27—H27	0.9300
C11—H11	0.9300	N1—S1	1.6464 (16)
C12—C13	1.388 (3)	N1—HN1	0.84 (2)
C12—H12	0.9300	N2—S2	1.6456 (16)
C13—H13	0.9300	N2—HN2	0.83 (2)
C14—O4	1.431 (3)	O1—S1	1.4167 (15)
C14—H14A	0.9600	O2—S1	1.4193 (15)
C14—H14B	0.9600	O5—S2	1.4229 (16)
C14—H14C	0.9600	O6—S2	1.4159 (17)
O8—C28—H28A	109.5	C15—C16—Cl2	122.57 (17)
O8—C28—H28B	109.5	C17—C16—Cl2	117.90 (16)
H28A—C28—H28B	109.5	C18—C17—C16	119.7 (2)
O8—C28—H28C	109.5	C18—C17—H17	120.1
H28A—C28—H28C	109.5	C16—C17—H17	120.1
H28B—C28—H28C	109.5	C19—C18—C17	121.0 (2)
C6—C1—C2	119.26 (18)	C19—C18—H18	119.5
C6—C1—S1	118.13 (14)	C17—C18—H18	119.5
C2—C1—S1	122.58 (14)	C18—C19—C20	119.6 (2)
C3—C2—C1	120.8 (2)	C18—C19—H19	120.2
C3—C2—Cl1	117.68 (17)	C20—C19—H19	120.2
C1—C2—Cl1	121.52 (15)	C15—C20—C19	120.67 (19)
C4—C3—C2	119.7 (2)	C15—C20—H20	119.7
C4—C3—H3	120.2	C19—C20—H20	119.7
C2—C3—H3	120.2	O7—C21—N2	120.38 (18)
C3—C4—C5	121.4 (2)	O7—C21—C22	122.59 (18)
C3—C4—H4	119.3	N2—C21—C22	117.03 (17)
C5—C4—H4	119.3	C27—C22—C23	117.87 (18)
C4—C5—C6	119.1 (2)	C27—C22—C21	115.59 (18)
C4—C5—H5	120.4	C23—C22—C21	126.54 (17)
C6—C5—H5	120.4	O8—C23—C24	122.1 (2)
C1—C6—C5	119.7 (2)	O8—C23—C22	117.77 (16)
C1—C6—H6	120.1	C24—C23—C22	120.1 (2)
C5—C6—H6	120.1	C25—C24—C23	120.4 (2)
O3—C7—N1	120.28 (18)	C25—C24—H24	119.8
O3—C7—C8	122.73 (18)	C23—C24—H24	119.8
N1—C7—C8	116.99 (17)	C26—C25—C24	120.7 (2)
C13—C8—C9	118.47 (18)	C26—C25—H25	119.7
C13—C8—C7	115.62 (18)	C24—C25—H25	119.7
C9—C8—C7	125.90 (17)	C25—C26—C27	119.5 (2)
O4—C9—C10	122.6 (2)	C25—C26—H26	120.3
O4—C9—C8	117.88 (16)	C27—C26—H26	120.3
C10—C9—C8	119.5 (2)	C26—C27—C22	121.4 (2)
C11—C10—C9	120.5 (2)	C26—C27—H27	119.3
C11—C10—H10	119.8	C22—C27—H27	119.3
C9—C10—H10	119.8	C7—N1—S1	124.23 (14)
C12—C11—C10	120.8 (2)	C7—N1—HN1	119.7 (15)
C12—C11—H11	119.6	S1—N1—HN1	115.3 (15)
C10—C11—H11	119.6	C21—N2—S2	123.34 (14)
C11—C12—C13	119.1 (2)	C21—N2—HN2	120.8 (15)
C11—C12—H12	120.4	S2—N2—HN2	113.6 (15)
C13—C12—H12	120.4	C9—O4—C14	118.77 (17)
C8—C13—C12	121.5 (2)	C23—O8—C28	118.52 (18)
C8—C13—H13	119.2	O1—S1—O2	118.75 (10)
C12—C13—H13	119.2	O1—S1—N1	104.48 (9)
O4—C14—H14A	109.5	O2—S1—N1	109.88 (9)
O4—C14—H14B	109.5	O1—S1—C1	110.61 (9)
H14A—C14—H14B	109.5	O2—S1—C1	107.38 (9)
O4—C14—H14C	109.5	N1—S1—C1	104.90 (8)
H14A—C14—H14C	109.5	O6—S2—O5	119.47 (11)
H14B—C14—H14C	109.5	O6—S2—N2	109.83 (10)
C20—C15—C16	119.46 (17)	O5—S2—N2	104.50 (9)
C20—C15—S2	116.91 (14)	O6—S2—C15	108.02 (9)
C16—C15—S2	123.60 (14)	O5—S2—C15	108.78 (9)
C15—C16—C17	119.53 (19)	N2—S2—C15	105.37 (8)
C6—C1—C2—C3	−0.8 (3)	O7—C21—C22—C23	−170.5 (2)
S1—C1—C2—C3	−178.80 (16)	N2—C21—C22—C23	9.9 (3)
C6—C1—C2—Cl1	179.04 (14)	C27—C22—C23—O8	−178.48 (18)
S1—C1—C2—Cl1	1.0 (2)	C21—C22—C23—O8	0.5 (3)
C1—C2—C3—C4	1.0 (3)	C27—C22—C23—C24	0.3 (3)
Cl1—C2—C3—C4	−178.82 (18)	C21—C22—C23—C24	179.3 (2)
C2—C3—C4—C5	−0.4 (4)	O8—C23—C24—C25	178.7 (2)
C3—C4—C5—C6	−0.5 (3)	C22—C23—C24—C25	0.0 (3)
C2—C1—C6—C5	−0.1 (3)	C23—C24—C25—C26	0.1 (4)
S1—C1—C6—C5	178.03 (15)	C24—C25—C26—C27	−0.5 (4)
C4—C5—C6—C1	0.7 (3)	C25—C26—C27—C22	0.9 (3)
O3—C7—C8—C13	−11.6 (3)	C23—C22—C27—C26	−0.8 (3)
N1—C7—C8—C13	168.32 (17)	C21—C22—C27—C26	−179.84 (19)
O3—C7—C8—C9	167.3 (2)	O3—C7—N1—S1	0.8 (3)
N1—C7—C8—C9	−12.8 (3)	C8—C7—N1—S1	−179.16 (13)
C13—C8—C9—O4	−179.34 (17)	O7—C21—N2—S2	4.3 (3)
C7—C8—C9—O4	1.8 (3)	C22—C21—N2—S2	−176.06 (14)
C13—C8—C9—C10	1.6 (3)	C10—C9—O4—C14	−7.3 (3)
C7—C8—C9—C10	−177.29 (18)	C8—C9—O4—C14	173.6 (2)
O4—C9—C10—C11	179.4 (2)	C24—C23—O8—C28	0.0 (4)
C8—C9—C10—C11	−1.5 (3)	C22—C23—O8—C28	178.8 (3)
C9—C10—C11—C12	0.2 (3)	C7—N1—S1—O1	−179.03 (16)
C10—C11—C12—C13	1.1 (4)	C7—N1—S1—O2	52.54 (18)
C9—C8—C13—C12	−0.3 (3)	C7—N1—S1—C1	−62.61 (17)
C7—C8—C13—C12	178.66 (19)	C6—C1—S1—O1	−128.77 (15)
C11—C12—C13—C8	−1.0 (3)	C2—C1—S1—O1	49.27 (17)
C20—C15—C16—C17	−1.9 (3)	C6—C1—S1—O2	2.24 (17)
S2—C15—C16—C17	175.80 (15)	C2—C1—S1—O2	−179.72 (15)
C20—C15—C16—Cl2	177.69 (14)	C6—C1—S1—N1	119.12 (15)
S2—C15—C16—Cl2	−4.6 (2)	C2—C1—S1—N1	−62.85 (17)
C15—C16—C17—C18	1.6 (3)	C21—N2—S2—O6	−61.0 (2)
Cl2—C16—C17—C18	−178.03 (18)	C21—N2—S2—O5	169.72 (18)
C16—C17—C18—C19	−0.1 (4)	C21—N2—S2—C15	55.13 (19)
C17—C18—C19—C20	−1.1 (3)	C20—C15—S2—O6	−7.14 (17)
C16—C15—C20—C19	0.8 (3)	C16—C15—S2—O6	175.07 (15)
S2—C15—C20—C19	−177.10 (15)	C20—C15—S2—O5	123.94 (15)
C18—C19—C20—C15	0.7 (3)	C16—C15—S2—O5	−53.85 (17)
O7—C21—C22—C27	8.5 (3)	C20—C15—S2—N2	−124.48 (15)
N2—C21—C22—C27	−171.13 (18)	C16—C15—S2—N2	57.73 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N1—HN1···O4	0.84 (2)	1.97 (2)	2.625 (2)	135 (2)
N2—HN2···O8	0.83 (2)	1.99 (2)	2.629 (3)	133 (2)
C13—H13···O3i	0.93	2.50	3.292 (3)	143
C10—H10···Cg	0.93	2.85	3.729 (3)	157

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C22–C27 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—HN1⋯O4	0.84 (2)	1.97 (2)	2.625 (2)	135 (2)
N2—HN2⋯O8	0.83 (2)	1.99 (2)	2.629 (3)	133 (2)
C13—H13⋯O3i	0.93	2.50	3.292 (3)	143
C10—H10⋯Cg	0.93	2.85	3.729 (3)	157

Symmetry code: (i) .