N-[4-(Ethyl-sulfamo-yl)phen-yl]acetamide.

The title compound, C(10)H(14)N(2)O(3)S, crystallized with two mol-ecules (A and B) in the asymmetric unit. The terminal methyl group of the ethyl-sulfonamide moiety in mol-ecule B is disordered over two sets of sites with an occupancy ratio of 0.61 (1):0.39 (1). Both mol-ecules have L-shaped conformations. In mol-ecule A, the dihedral angles between the benzene ring and its ethyl-sulfonamide and methyl-amide substituents are 83.5 (3) and 13.34 (18)°, respectively. Equivalent values for mol-ecule B are 87.9 (3) and 6.32 (16)°, respectively. The C-S-N-C torsion angles are 66.5 (3)° for A and -64.4 (3)° for B, indicating similar twists about the S-N bonds, but in opposite senses. In the crystal, the A mol-ecules are linked by pairs of N(s)-H⋯O (s = sulfonamide) hydrogen bonds, generating inversion dimers containing R(2) (2)(8) rings, while the B mol-ecules are linked by N(s)-H⋯O hydrogen bonds into C(10) [100] chains. Finally, N(a)-H⋯O (a = amide) hydrogen bonds link the A-mol-ecule dimers and B-mol-ecule chains into a three-dimensional network.

Related literature

For related structures, see: Hou et al. (2009 ▶); Khan et al. (2011 ▶); Rehman et al. (2011 ▶).

Experimental

Crystal data

C10H14N2O3S

M = 242.29

Triclinic,

a = 8.2766 (3) Å

b = 12.1728 (4) Å

c = 13.5041 (4) Å

α = 70.130 (2)°

β = 73.935 (2)°

γ = 71.517 (2)°

V = 1191.56 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.27 mm−1

T = 296 K

0.40 × 0.35 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.901, T max = 0.949

18017 measured reflections

4310 independent reflections

2701 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.117

S = 1.04

4310 reflections

317 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.29 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811033472/su2301sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811033472/su2301Isup2.hkl

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

C10H14N2O3S	Z = 4
Mr = 242.29	F(000) = 512
Triclinic, P1	Dx = 1.351 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.2766 (3) Å	Cell parameters from 2513 reflections
b = 12.1728 (4) Å	θ = 2.6–23.2°
c = 13.5041 (4) Å	µ = 0.27 mm−1
α = 70.130 (2)°	T = 296 K
β = 73.935 (2)°	Block, colourless
γ = 71.517 (2)°	0.40 × 0.35 × 0.20 mm
V = 1191.56 (7) Å3

Bruker APEXII CCD diffractometer	4310 independent reflections
Radiation source: fine-focus sealed tube	2701 reflections with I > 2σ(I)
graphite	Rint = 0.049
ω scans	θmax = 25.3°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→9
Tmin = 0.901, Tmax = 0.949	k = −14→14
18017 measured reflections	l = −16→16

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0542P)2] where P = (Fo2 + 2Fc2)/3
4310 reflections	(Δ/σ)max = 0.001
317 parameters	Δρmax = 0.23 e Å−3
4 restraints	Δρmin = −0.29 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	Occ. (<1)
C1	0.2008 (3)	0.0487 (2)	0.95681 (17)	0.0464 (6)
C2	0.1609 (3)	0.1059 (2)	0.85534 (17)	0.0505 (7)
H2	0.1827	0.0615	0.8069	0.061*
C3	0.0899 (4)	0.2270 (2)	0.82678 (18)	0.0525 (7)
H3	0.0648	0.2649	0.7584	0.063*
C4	0.0548 (4)	0.2939 (2)	0.89748 (18)	0.0520 (7)
C5	0.0892 (5)	0.2362 (3)	1.0001 (2)	0.0727 (10)
H5	0.0637	0.2801	1.0494	0.087*
C6	0.1599 (4)	0.1162 (3)	1.02838 (19)	0.0704 (9)
H6	0.1816	0.0782	1.0976	0.084*
C7	0.3582 (4)	−0.1539 (2)	0.9343 (2)	0.0515 (7)
C8	0.4335 (4)	−0.2783 (3)	0.9973 (2)	0.0711 (9)
H8A	0.4104	−0.2813	1.0717	0.107*	0.50
H8B	0.5566	−0.2995	0.9720	0.107*	0.50
H8C	0.3820	−0.3341	0.9887	0.107*	0.50
H8D	0.4889	−0.3286	0.9499	0.107*	0.50
H8E	0.3428	−0.3104	1.0496	0.107*	0.50
H8F	0.5173	−0.2758	1.0329	0.107*	0.50
C9	0.2775 (5)	0.5052 (4)	0.7663 (3)	0.1020 (13)
H9A	0.2468	0.5355	0.6958	0.122*
H9B	0.3408	0.4214	0.7761	0.122*
C10	0.3891 (6)	0.5758 (4)	0.7731 (3)	0.1241 (16)
H10A	0.3247	0.6580	0.7662	0.186*
H10B	0.4890	0.5726	0.7164	0.186*
H10C	0.4257	0.5423	0.8410	0.186*
S1	−0.02930 (11)	0.45083 (7)	0.85864 (5)	0.0632 (3)
O1	−0.0688 (3)	0.48292 (18)	0.75523 (15)	0.0899 (8)
O2	−0.1616 (3)	0.48336 (18)	0.94495 (15)	0.0701 (6)
O3	0.3705 (3)	−0.12737 (18)	0.83768 (13)	0.0745 (6)
N1	0.1197 (4)	0.5143 (2)	0.8485 (2)	0.0677 (8)
H1N	0.132 (4)	0.509 (3)	0.906 (2)	0.084 (12)*
N2	0.2774 (3)	−0.0745 (2)	0.99202 (17)	0.0509 (6)
H2N	0.273 (3)	−0.098 (2)	1.0556 (19)	0.057 (8)*
C11	0.5045 (3)	0.8474 (2)	0.55157 (16)	0.0400 (6)
C12	0.3254 (3)	0.8783 (2)	0.57472 (17)	0.0464 (7)
H12	0.2680	0.8955	0.6394	0.056*
C13	0.2316 (3)	0.8836 (2)	0.50377 (17)	0.0462 (6)
H13	0.1110	0.9035	0.5205	0.055*
C14	0.3162 (3)	0.8595 (2)	0.40685 (16)	0.0429 (6)
C15	0.4946 (4)	0.8336 (2)	0.38109 (18)	0.0530 (7)
H15	0.5516	0.8194	0.3152	0.064*
C16	0.5891 (4)	0.8287 (2)	0.45299 (18)	0.0542 (7)
H16	0.7095	0.8127	0.4350	0.065*
C17	0.7625 (4)	0.8011 (2)	0.63274 (19)	0.0471 (6)
C18	0.8106 (4)	0.7976 (3)	0.7326 (2)	0.0613 (8)
H18A	0.7076	0.8236	0.7814	0.092*	0.50
H18B	0.8859	0.8502	0.7151	0.092*	0.50
H18C	0.8694	0.7167	0.7655	0.092*	0.50
H18D	0.9343	0.7701	0.7266	0.092*	0.50
H18E	0.7560	0.7435	0.7929	0.092*	0.50
H18F	0.7725	0.8769	0.7425	0.092*	0.50
C19	0.2575 (5)	0.6154 (3)	0.3897 (3)	0.0936 (11)
H19A	0.3533	0.6220	0.4139	0.112*	0.61
H19B	0.3027	0.6012	0.3196	0.112*	0.61
H19C	0.2166	0.5623	0.3680	0.112*	0.39
H19D	0.3637	0.6287	0.3398	0.112*	0.39
C20A	0.1990 (9)	0.5089 (5)	0.4637 (5)	0.109 (2)	0.61
H20A	0.2979	0.4448	0.4832	0.131*	0.61
H20B	0.1359	0.4833	0.4293	0.131*	0.61
H20C	0.1251	0.5289	0.5270	0.131*	0.61
C20B	0.2956 (10)	0.5581 (9)	0.4878 (7)	0.097 (3)	0.39
H20D	0.3904	0.4885	0.4843	0.116*	0.39
H20E	0.1959	0.5334	0.5361	0.116*	0.39
H20F	0.3276	0.6115	0.5133	0.116*	0.39
S2	0.19472 (9)	0.85254 (7)	0.32215 (5)	0.0510 (2)
O4	0.3107 (3)	0.84047 (18)	0.22380 (12)	0.0666 (6)
O5	0.0430 (3)	0.94944 (18)	0.31922 (14)	0.0715 (6)
O6	0.8709 (2)	0.7722 (2)	0.55920 (14)	0.0725 (6)
N3	0.1303 (3)	0.7306 (2)	0.37712 (18)	0.0558 (7)
H3N	0.054 (4)	0.737 (3)	0.431 (2)	0.074 (10)*
N4	0.5909 (3)	0.8385 (2)	0.63127 (17)	0.0464 (6)
H4N	0.531 (3)	0.852 (2)	0.6812 (19)	0.048 (9)*

	U11	U22	U33	U12	U13	U23
C1	0.0546 (17)	0.0509 (17)	0.0336 (12)	−0.0121 (14)	−0.0065 (12)	−0.0141 (11)
C2	0.0633 (19)	0.0566 (18)	0.0351 (13)	−0.0090 (15)	−0.0115 (12)	−0.0208 (12)
C3	0.0663 (19)	0.0571 (19)	0.0360 (13)	−0.0076 (16)	−0.0162 (13)	−0.0170 (12)
C4	0.0681 (19)	0.0490 (16)	0.0412 (13)	−0.0069 (15)	−0.0184 (13)	−0.0159 (12)
C5	0.121 (3)	0.058 (2)	0.0444 (15)	−0.0006 (19)	−0.0344 (17)	−0.0244 (13)
C6	0.118 (3)	0.0550 (19)	0.0365 (14)	0.0003 (19)	−0.0320 (16)	−0.0167 (13)
C7	0.0550 (18)	0.0552 (18)	0.0432 (15)	−0.0082 (15)	−0.0049 (13)	−0.0207 (13)
C8	0.085 (2)	0.060 (2)	0.0606 (17)	−0.0049 (18)	−0.0142 (17)	−0.0184 (15)
C9	0.124 (3)	0.106 (3)	0.073 (2)	−0.041 (3)	0.021 (2)	−0.040 (2)
C10	0.134 (4)	0.087 (3)	0.138 (3)	−0.053 (3)	0.030 (3)	−0.034 (2)
S1	0.0857 (6)	0.0535 (5)	0.0532 (4)	−0.0020 (4)	−0.0284 (4)	−0.0203 (3)
O1	0.148 (2)	0.0633 (14)	0.0648 (12)	0.0019 (14)	−0.0616 (14)	−0.0176 (10)
O2	0.0702 (14)	0.0692 (14)	0.0750 (12)	0.0001 (11)	−0.0216 (11)	−0.0347 (10)
O3	0.0948 (16)	0.0751 (14)	0.0430 (11)	0.0051 (12)	−0.0103 (10)	−0.0294 (9)
N1	0.093 (2)	0.0600 (17)	0.0555 (16)	−0.0215 (15)	−0.0127 (16)	−0.0210 (13)
N2	0.0678 (16)	0.0517 (15)	0.0290 (11)	−0.0086 (12)	−0.0089 (11)	−0.0119 (10)
C11	0.0441 (16)	0.0447 (15)	0.0336 (12)	−0.0111 (13)	−0.0067 (11)	−0.0144 (10)
C12	0.0491 (17)	0.0536 (17)	0.0358 (13)	−0.0067 (14)	−0.0049 (12)	−0.0194 (11)
C13	0.0398 (15)	0.0555 (17)	0.0418 (13)	−0.0039 (13)	−0.0085 (12)	−0.0184 (12)
C14	0.0486 (17)	0.0481 (16)	0.0323 (12)	−0.0096 (13)	−0.0108 (11)	−0.0110 (11)
C15	0.0506 (17)	0.075 (2)	0.0350 (13)	−0.0133 (15)	−0.0029 (12)	−0.0230 (12)
C16	0.0415 (16)	0.080 (2)	0.0440 (14)	−0.0141 (15)	−0.0045 (12)	−0.0249 (13)
C17	0.0523 (18)	0.0467 (16)	0.0437 (14)	−0.0129 (14)	−0.0150 (13)	−0.0088 (12)
C18	0.0623 (19)	0.068 (2)	0.0596 (16)	−0.0101 (16)	−0.0260 (15)	−0.0193 (14)
C19	0.095 (3)	0.063 (2)	0.115 (3)	−0.013 (2)	−0.005 (2)	−0.034 (2)
C20A	0.187 (8)	0.071 (4)	0.080 (4)	−0.046 (5)	−0.037 (4)	−0.011 (3)
C20B	0.107 (8)	0.092 (8)	0.089 (7)	−0.002 (6)	−0.035 (6)	−0.030 (6)
S2	0.0567 (5)	0.0621 (5)	0.0360 (3)	−0.0101 (4)	−0.0169 (3)	−0.0136 (3)
O4	0.0735 (14)	0.1001 (16)	0.0299 (9)	−0.0264 (12)	−0.0085 (9)	−0.0191 (9)
O5	0.0702 (14)	0.0710 (14)	0.0708 (12)	0.0101 (12)	−0.0408 (11)	−0.0199 (10)
O6	0.0473 (12)	0.1133 (18)	0.0551 (11)	−0.0118 (12)	−0.0038 (10)	−0.0331 (11)
N3	0.0559 (16)	0.0708 (18)	0.0482 (13)	−0.0185 (14)	−0.0073 (12)	−0.0253 (12)
N4	0.0441 (15)	0.0603 (15)	0.0364 (12)	−0.0083 (12)	−0.0064 (11)	−0.0206 (11)

C1—C6	1.381 (3)	C12—H12	0.9300
C1—C2	1.388 (3)	C13—C14	1.383 (3)
C1—N2	1.399 (3)	C13—H13	0.9300
C2—C3	1.363 (3)	C14—C15	1.377 (3)
C2—H2	0.9300	C14—S2	1.756 (2)
C3—C4	1.373 (3)	C15—C16	1.381 (3)
C3—H3	0.9300	C15—H15	0.9300
C4—C5	1.388 (3)	C16—H16	0.9300
C4—S1	1.756 (3)	C17—O6	1.208 (3)
C5—C6	1.351 (4)	C17—N4	1.351 (3)
C5—H5	0.9300	C17—C18	1.492 (3)
C6—H6	0.9300	C18—H18A	0.9600
C7—O3	1.215 (3)	C18—H18B	0.9600
C7—N2	1.343 (3)	C18—H18C	0.9600
C7—C8	1.491 (4)	C18—H18D	0.9600
C8—H8A	0.9600	C18—H18E	0.9600
C8—H8B	0.9600	C18—H18F	0.9600
C8—H8C	0.9600	C19—C20B	1.343 (8)
C8—H8D	0.9600	C19—N3	1.451 (4)
C8—H8E	0.9600	C19—C20A	1.471 (6)
C8—H8F	0.9600	C19—H19A	0.9700
C9—N1	1.463 (4)	C19—H19B	0.9700
C9—C10	1.484 (5)	C19—H19C	0.9700
C9—H9A	0.9700	C19—H19D	0.9700
C9—H9B	0.9700	C20A—H19C	1.2249
C10—H10A	0.9600	C20A—H20A	0.9600
C10—H10B	0.9600	C20A—H20B	0.9600
C10—H10C	0.9600	C20A—H20C	0.9600
S1—O1	1.4180 (19)	C20B—H20D	0.9600
S1—O2	1.431 (2)	C20B—H20E	0.9600
S1—N1	1.605 (3)	C20B—H20F	0.9600
N1—H1N	0.79 (3)	S2—O5	1.424 (2)
N2—H2N	0.80 (2)	S2—O4	1.4298 (17)
C11—C16	1.380 (3)	S2—N3	1.604 (2)
C11—C12	1.381 (3)	N3—H3N	0.83 (3)
C11—N4	1.407 (3)	N4—H4N	0.75 (2)
C12—C13	1.364 (3)
C6—C1—C2	118.5 (2)	C13—C14—S2	119.3 (2)
C6—C1—N2	117.6 (2)	C14—C15—C16	120.1 (2)
C2—C1—N2	123.8 (2)	C14—C15—H15	120.0
C3—C2—C1	119.9 (2)	C16—C15—H15	120.0
C3—C2—H2	120.0	C11—C16—C15	119.9 (2)
C1—C2—H2	120.0	C11—C16—H16	120.1
C2—C3—C4	121.0 (2)	C15—C16—H16	120.1
C2—C3—H3	119.5	O6—C17—N4	123.2 (2)
C4—C3—H3	119.5	O6—C17—C18	121.6 (3)
C3—C4—C5	119.1 (2)	N4—C17—C18	115.2 (2)
C3—C4—S1	120.80 (19)	C17—C18—H18A	109.5
C5—C4—S1	120.1 (2)	C17—C18—H18B	109.5
C6—C5—C4	119.9 (2)	H18A—C18—H18B	109.5
C6—C5—H5	120.0	C17—C18—H18C	109.5
C4—C5—H5	120.0	H18A—C18—H18C	109.5
C5—C6—C1	121.5 (2)	H18B—C18—H18C	109.5
C5—C6—H6	119.3	C17—C18—H18D	109.5
C1—C6—H6	119.3	H18A—C18—H18D	141.1
O3—C7—N2	123.0 (3)	H18B—C18—H18D	56.3
O3—C7—C8	121.9 (2)	H18C—C18—H18D	56.3
N2—C7—C8	115.1 (2)	C17—C18—H18E	109.5
C7—C8—H8A	109.5	H18A—C18—H18E	56.3
C7—C8—H8B	109.5	H18B—C18—H18E	141.1
H8A—C8—H8B	109.5	H18C—C18—H18E	56.3
C7—C8—H8C	109.5	H18D—C18—H18E	109.5
H8A—C8—H8C	109.5	C17—C18—H18F	109.5
H8B—C8—H8C	109.5	H18A—C18—H18F	56.3
C7—C8—H8D	109.5	H18B—C18—H18F	56.3
H8A—C8—H8D	141.1	H18C—C18—H18F	141.1
H8B—C8—H8D	56.3	H18D—C18—H18F	109.5
H8C—C8—H8D	56.3	H18E—C18—H18F	109.5
C7—C8—H8E	109.5	C20B—C19—N3	117.2 (5)
H8A—C8—H8E	56.3	C20B—C19—C20A	54.7 (4)
H8B—C8—H8E	141.1	N3—C19—C20A	117.3 (4)
H8C—C8—H8E	56.3	C20B—C19—H19A	55.6
H8D—C8—H8E	109.5	N3—C19—H19A	108.0
C7—C8—H8F	109.5	C20A—C19—H19A	108.0
H8A—C8—H8F	56.3	C20B—C19—H19B	134.6
H8B—C8—H8F	56.3	N3—C19—H19B	108.0
H8C—C8—H8F	141.1	C20A—C19—H19B	108.0
H8D—C8—H8F	109.5	H19A—C19—H19B	107.2
H8E—C8—H8F	109.5	C20B—C19—H19C	108.1
N1—C9—C10	110.3 (3)	N3—C19—H19C	108.0
N1—C9—H9A	109.6	C20A—C19—H19C	55.8
C10—C9—H9A	109.6	H19A—C19—H19C	143.9
N1—C9—H9B	109.6	H19B—C19—H19C	58.7
C10—C9—H9B	109.6	C20B—C19—H19D	108.4
H9A—C9—H9B	108.1	N3—C19—H19D	107.5
C9—C10—H10A	109.5	C20A—C19—H19D	135.0
C9—C10—H10B	109.5	H19A—C19—H19D	59.1
H10A—C10—H10B	109.5	H19B—C19—H19D	50.6
C9—C10—H10C	109.5	H19C—C19—H19D	107.2
H10A—C10—H10C	109.5	C19—C20A—H19C	40.9
H10B—C10—H10C	109.5	C19—C20A—H20A	109.5
O1—S1—O2	119.76 (14)	H19C—C20A—H20A	113.9
O1—S1—N1	107.58 (15)	C19—C20A—H20B	109.5
O2—S1—N1	104.88 (13)	H19C—C20A—H20B	70.0
O1—S1—C4	107.82 (12)	C19—C20A—H20C	109.5
O2—S1—C4	108.01 (12)	H19C—C20A—H20C	133.9
N1—S1—C4	108.34 (14)	C19—C20B—H20D	109.5
C9—N1—S1	121.8 (2)	C19—C20B—H20E	109.5
C9—N1—H1N	116 (3)	H20D—C20B—H20E	109.5
S1—N1—H1N	110 (2)	C19—C20B—H20F	109.5
C7—N2—C1	129.0 (2)	H20D—C20B—H20F	109.5
C7—N2—H2N	117.9 (19)	H20E—C20B—H20F	109.5
C1—N2—H2N	113.0 (19)	O5—S2—O4	119.04 (11)
C16—C11—C12	119.4 (2)	O5—S2—N3	106.63 (14)
C16—C11—N4	123.5 (2)	O4—S2—N3	107.26 (13)
C12—C11—N4	117.0 (2)	O5—S2—C14	109.07 (12)
C13—C12—C11	120.7 (2)	O4—S2—C14	107.35 (12)
C13—C12—H12	119.6	N3—S2—C14	106.90 (11)
C11—C12—H12	119.6	C19—N3—S2	119.3 (2)
C12—C13—C14	119.9 (2)	C19—N3—H3N	115 (2)
C12—C13—H13	120.1	S2—N3—H3N	110 (2)
C14—C13—H13	120.1	C17—N4—C11	128.9 (2)
C15—C14—C13	119.8 (2)	C17—N4—H4N	117 (2)
C15—C14—S2	120.78 (18)	C11—N4—H4N	114 (2)
C6—C1—C2—C3	2.8 (4)	N4—C11—C12—C13	−177.1 (2)
N2—C1—C2—C3	−178.5 (2)	C11—C12—C13—C14	−0.8 (4)
C1—C2—C3—C4	−0.8 (4)	C12—C13—C14—C15	−1.9 (4)
C2—C3—C4—C5	−1.3 (4)	C12—C13—C14—S2	173.90 (19)
C2—C3—C4—S1	177.6 (2)	C13—C14—C15—C16	1.7 (4)
C3—C4—C5—C6	1.5 (5)	S2—C14—C15—C16	−174.1 (2)
S1—C4—C5—C6	−177.5 (3)	C12—C11—C16—C15	−3.9 (4)
C4—C5—C6—C1	0.6 (5)	N4—C11—C16—C15	176.9 (2)
C2—C1—C6—C5	−2.7 (5)	C14—C15—C16—C11	1.3 (4)
N2—C1—C6—C5	178.5 (3)	C15—C14—S2—O5	−141.0 (2)
C3—C4—S1—O1	7.2 (3)	C13—C14—S2—O5	43.2 (2)
C5—C4—S1—O1	−173.8 (3)	C15—C14—S2—O4	−10.8 (3)
C3—C4—S1—O2	138.0 (2)	C13—C14—S2—O4	173.46 (19)
C5—C4—S1—O2	−43.1 (3)	C15—C14—S2—N3	104.0 (2)
C3—C4—S1—N1	−108.9 (3)	C13—C14—S2—N3	−71.7 (2)
C5—C4—S1—N1	70.0 (3)	C20B—C19—N3—S2	102.6 (6)
C10—C9—N1—S1	178.0 (3)	C20A—C19—N3—S2	164.8 (4)
O1—S1—N1—C9	−49.8 (3)	O5—S2—N3—C19	179.1 (2)
O2—S1—N1—C9	−178.3 (3)	O4—S2—N3—C19	50.5 (3)
C4—S1—N1—C9	66.5 (3)	C14—S2—N3—C19	−64.4 (3)
O3—C7—N2—C1	−2.7 (5)	O6—C17—N4—C11	2.5 (4)
C8—C7—N2—C1	177.0 (3)	C18—C17—N4—C11	−177.5 (2)
C6—C1—N2—C7	−166.0 (3)	C16—C11—N4—C17	−6.6 (4)
C2—C1—N2—C7	15.2 (4)	C12—C11—N4—C17	174.2 (3)
C16—C11—C12—C13	3.7 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.79 (3)	2.13 (3)	2.914 (3)	173 (3)
N2—H2N···O4ii	0.80 (2)	2.21 (2)	3.006 (3)	169 (3)
N3—H3N···O6iii	0.83 (3)	2.03 (3)	2.854 (3)	173 (3)
N4—H4N···O3iv	0.75 (2)	2.21 (2)	2.960 (3)	174 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.79 (3)	2.13 (3)	2.914 (3)	173 (3)
N2—H2N⋯O4ii	0.80 (2)	2.21 (2)	3.006 (3)	169 (3)
N3—H3N⋯O6iii	0.83 (3)	2.03 (3)	2.854 (3)	173 (3)
N4—H4N⋯O3iv	0.75 (2)	2.21 (2)	2.960 (3)	174 (3)

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