Diethyl 2,2'-[(5-dimethyl-amino-1-naphth-yl)sulfonyl-imino]diacetate.

In the title compound, C(20)H(26)N(2)O(6)S, the N atom of the dimethyl-amino group is displaced by 0.113 (2) Å from the plane of the naphthalene ring system. The two eth-oxy groups adopt zigzag conformations. In the crystal structure, weak inter-molecular C-H⋯O hydrogen bonds link the mol-ecules, forming a three-dimensional network. Both ethyl groups are disordered over two sites with the ratios of refined occupancies being 0.857 (16):0.143 (16) and 0.517 (14):0.483 (14).

Related literature

For applications of ligands containing the 5-(dimethyl­amino) naphthalene-1-sulfonyl (dans­yl) group, see: Corradini et al. (1997 ▶); Christoforou et al. (2006 ▶); Zhang et al. (2009 ▶).

Experimental

Crystal data

C20H26N2O6S

M = 422.49

Monoclinic,

a = 13.1266 (9) Å

b = 8.4592 (5) Å

c = 19.3206 (12) Å

β = 93.530 (1)°

V = 2141.3 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.19 mm−1

T = 298 K

0.20 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.970, T max = 0.981

16359 measured reflections

4201 independent reflections

3705 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.145

S = 1.05

4201 reflections

306 parameters

12 restraints

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.27 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT-Plus (Bruker, 2007 ▶); data reduction: SAIn class="Chemical">NT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809041476/lh2912sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809041476/lh2912Isup2.hkl

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

C20H26N2O6S	F(000) = 896
Mr = 422.49	Dx = 1.311 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7099 reflections
a = 13.1266 (9) Å	θ = 2.4–27.8°
b = 8.4592 (5) Å	µ = 0.19 mm−1
c = 19.3206 (12) Å	T = 298 K
β = 93.530 (1)°	Block, yellow
V = 2141.3 (2) Å3	0.20 × 0.20 × 0.20 mm
Z = 4

Bruker SMART CCD diffractometer	4201 independent reflections
Radiation source: fine-focus sealed tube	3705 reflections with I > 2σ(I)
graphite	Rint = 0.040
φ and ω scans	θmax = 26.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→16
Tmin = 0.970, Tmax = 0.981	k = −10→10
16359 measured reflections	l = −23→23

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0753P)2 + 0.7093P] where P = (Fo2 + 2Fc2)/3
4201 reflections	(Δ/σ)max < 0.001
306 parameters	Δρmax = 0.35 e Å−3
12 restraints	Δρmin = −0.27 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	Occ. (<1)
C1	0.95264 (17)	0.5912 (3)	0.37909 (11)	0.0578 (5)
C2	1.02352 (18)	0.4871 (3)	0.35796 (14)	0.0715 (7)
H2	1.0911	0.4969	0.3750	0.086*
C3	0.99669 (18)	0.3659 (3)	0.31122 (15)	0.0737 (7)
H3	1.0466	0.2959	0.2981	0.088*
C4	0.89929 (16)	0.3482 (3)	0.28453 (13)	0.0622 (6)
H4	0.8836	0.2689	0.2523	0.075*
C5	0.82149 (15)	0.4499 (2)	0.30558 (10)	0.0466 (4)
C6	0.71621 (15)	0.4373 (2)	0.28232 (10)	0.0446 (4)
C7	0.64297 (16)	0.5326 (2)	0.30780 (11)	0.0522 (5)
H7	0.5752	0.5227	0.2912	0.063*
C8	0.67007 (17)	0.6443 (3)	0.35867 (12)	0.0588 (5)
H8	0.6200	0.7065	0.3771	0.071*
C9	0.76932 (17)	0.6628 (3)	0.38138 (12)	0.0575 (5)
H9	0.7861	0.7382	0.4153	0.069*
C10	0.84776 (15)	0.5708 (2)	0.35492 (10)	0.0490 (5)
C11	0.9684 (3)	0.8725 (4)	0.39713 (18)	0.0941 (10)
H11A	1.0269	0.8936	0.3712	0.141*
H11B	0.9651	0.9487	0.4337	0.141*
H11C	0.9076	0.8794	0.3669	0.141*
C12	1.0732 (2)	0.6972 (5)	0.46859 (16)	0.0957 (10)
H12A	1.0791	0.5906	0.4854	0.144*
H12B	1.0742	0.7688	0.5072	0.144*
H12C	1.1293	0.7203	0.4406	0.144*
C13	0.59995 (17)	0.1130 (3)	0.32052 (11)	0.0548 (5)
H13A	0.5668	0.0108	0.3159	0.066*
H13B	0.5478	0.1937	0.3136	0.066*
C14	0.64919 (19)	0.1283 (3)	0.39272 (12)	0.0588 (5)
C15	0.6061 (8)	0.1733 (7)	0.5102 (2)	0.0874 (19)	0.857 (16)
H15A	0.6740	0.1337	0.5230	0.105*	0.857 (16)
H15B	0.5583	0.1241	0.5399	0.105*	0.857 (16)
C16	0.6032 (10)	0.3472 (8)	0.5176 (3)	0.149 (4)	0.857 (16)
H16A	0.6565	0.3935	0.4925	0.223*	0.857 (16)
H16B	0.6128	0.3748	0.5658	0.223*	0.857 (16)
H16C	0.5383	0.3861	0.4994	0.223*	0.857 (16)
C17	0.73411 (17)	−0.0060 (3)	0.24933 (12)	0.0552 (5)
H17A	0.7484	−0.0699	0.2905	0.066*
H17B	0.7988	0.0315	0.2339	0.066*
C18	0.68302 (16)	−0.1075 (2)	0.19336 (11)	0.0520 (5)
C19	0.7087 (7)	−0.2942 (12)	0.1072 (5)	0.073 (3)	0.517 (14)
H19A	0.6722	−0.2204	0.0762	0.088*	0.517 (14)
H19B	0.6624	−0.3784	0.1185	0.088*	0.517 (14)
C20	0.8001 (6)	−0.3609 (15)	0.0734 (5)	0.100 (3)	0.517 (14)
H20A	0.8432	−0.2759	0.0600	0.150*	0.517 (14)
H20B	0.7776	−0.4207	0.0331	0.150*	0.517 (14)
H20C	0.8378	−0.4285	0.1057	0.150*	0.517 (14)
C15'	0.626 (2)	0.223 (5)	0.4978 (12)	0.069 (9)	0.143 (16)
H15C	0.6659	0.3117	0.4825	0.083*	0.143 (16)
H15D	0.6711	0.1531	0.5253	0.083*	0.143 (16)
C16'	0.539 (3)	0.281 (6)	0.5403 (16)	0.122 (14)	0.143 (16)
H16D	0.5088	0.3735	0.5189	0.182*	0.143 (16)
H16E	0.5652	0.3060	0.5864	0.182*	0.143 (16)
H16F	0.4883	0.1993	0.5421	0.182*	0.143 (16)
C19'	0.7221 (11)	−0.3420 (9)	0.1268 (4)	0.069 (3)	0.483 (14)
H19C	0.6507	−0.3697	0.1290	0.083*	0.483 (14)
H19D	0.7638	−0.4342	0.1382	0.083*	0.483 (14)
C20'	0.7438 (12)	−0.2768 (12)	0.0564 (4)	0.101 (4)	0.483 (14)
H20D	0.7039	−0.1831	0.0474	0.152*	0.483 (14)
H20E	0.7263	−0.3544	0.0215	0.152*	0.483 (14)
H20F	0.8150	−0.2515	0.0556	0.152*	0.483 (14)
N1	0.97658 (16)	0.7153 (3)	0.42652 (11)	0.0706 (6)
N2	0.67264 (13)	0.1287 (2)	0.26716 (9)	0.0524 (4)
O1	0.74296 (13)	0.2660 (2)	0.16995 (8)	0.0631 (4)
O2	0.56924 (12)	0.3303 (2)	0.20057 (8)	0.0635 (4)
O3	0.73809 (15)	0.1308 (3)	0.40732 (10)	0.0988 (7)
O4	0.57813 (15)	0.1376 (3)	0.43757 (9)	0.0934 (7)
O5	0.59653 (12)	−0.0973 (2)	0.17180 (10)	0.0751 (5)
O6	0.74949 (13)	−0.2111 (2)	0.17216 (11)	0.0783 (6)
S1	0.67202 (4)	0.28980 (6)	0.22222 (3)	0.04759 (18)

	U11	U22	U33	U12	U13	U23
C1	0.0469 (12)	0.0728 (14)	0.0531 (12)	−0.0099 (10)	−0.0019 (9)	0.0004 (10)
C2	0.0377 (12)	0.0952 (19)	0.0807 (17)	−0.0057 (12)	−0.0047 (11)	−0.0049 (14)
C3	0.0409 (12)	0.0834 (18)	0.0969 (19)	0.0088 (12)	0.0039 (12)	−0.0136 (15)
C4	0.0439 (12)	0.0645 (13)	0.0783 (15)	0.0032 (10)	0.0028 (10)	−0.0126 (12)
C5	0.0390 (10)	0.0492 (10)	0.0516 (11)	−0.0017 (8)	0.0024 (8)	0.0026 (9)
C6	0.0416 (10)	0.0439 (10)	0.0479 (10)	−0.0013 (8)	−0.0012 (8)	0.0002 (8)
C7	0.0409 (11)	0.0525 (11)	0.0625 (12)	0.0024 (9)	−0.0020 (9)	−0.0013 (10)
C8	0.0492 (12)	0.0585 (12)	0.0691 (14)	0.0070 (10)	0.0073 (10)	−0.0115 (11)
C9	0.0574 (13)	0.0585 (12)	0.0567 (12)	−0.0042 (10)	0.0027 (10)	−0.0115 (10)
C10	0.0433 (11)	0.0553 (11)	0.0481 (11)	−0.0033 (9)	−0.0003 (8)	0.0032 (9)
C11	0.094 (2)	0.086 (2)	0.100 (2)	−0.0227 (17)	−0.0109 (18)	−0.0207 (18)
C12	0.0681 (18)	0.139 (3)	0.0770 (18)	−0.0235 (18)	−0.0197 (14)	−0.0136 (18)
C13	0.0504 (12)	0.0551 (12)	0.0586 (12)	−0.0068 (9)	0.0010 (9)	−0.0018 (10)
C14	0.0591 (14)	0.0581 (13)	0.0587 (13)	0.0007 (11)	0.0002 (11)	−0.0021 (10)
C15	0.106 (4)	0.108 (4)	0.048 (2)	0.013 (3)	0.008 (2)	0.010 (2)
C16	0.252 (12)	0.115 (4)	0.075 (3)	0.068 (5)	−0.026 (4)	−0.014 (3)
C17	0.0509 (12)	0.0492 (11)	0.0642 (13)	0.0078 (9)	−0.0064 (10)	−0.0050 (9)
C18	0.0450 (12)	0.0507 (11)	0.0612 (12)	−0.0067 (9)	0.0104 (9)	−0.0046 (9)
C19	0.070 (4)	0.055 (5)	0.093 (7)	0.002 (4)	−0.003 (5)	−0.027 (5)
C20	0.091 (5)	0.108 (7)	0.103 (5)	0.003 (4)	0.019 (4)	−0.038 (5)
C15'	0.078 (16)	0.09 (2)	0.044 (12)	0.002 (13)	0.007 (11)	0.002 (13)
C16'	0.11 (3)	0.13 (3)	0.12 (2)	0.04 (2)	−0.006 (19)	0.01 (2)
C19'	0.092 (7)	0.044 (4)	0.074 (4)	−0.011 (4)	0.018 (4)	−0.005 (3)
C20'	0.153 (11)	0.085 (6)	0.067 (4)	−0.032 (6)	0.025 (5)	−0.010 (4)
N1	0.0575 (12)	0.0899 (16)	0.0630 (12)	−0.0152 (11)	−0.0086 (9)	−0.0105 (11)
N2	0.0545 (10)	0.0458 (9)	0.0570 (10)	0.0032 (8)	0.0041 (8)	−0.0042 (8)
O1	0.0666 (10)	0.0730 (10)	0.0499 (8)	0.0011 (8)	0.0046 (7)	−0.0043 (7)
O2	0.0521 (9)	0.0667 (9)	0.0688 (10)	0.0086 (7)	−0.0194 (7)	−0.0052 (8)
O3	0.0622 (12)	0.161 (2)	0.0711 (12)	0.0146 (13)	−0.0128 (9)	−0.0102 (13)
O4	0.0767 (13)	0.1434 (19)	0.0607 (11)	−0.0036 (13)	0.0095 (9)	−0.0127 (12)
O5	0.0455 (9)	0.0878 (12)	0.0910 (12)	−0.0035 (8)	−0.0051 (8)	−0.0257 (10)
O6	0.0566 (10)	0.0703 (11)	0.1090 (14)	−0.0017 (8)	0.0126 (9)	−0.0396 (10)
S1	0.0445 (3)	0.0501 (3)	0.0474 (3)	0.0023 (2)	−0.0045 (2)	−0.0020 (2)

C1—C2	1.362 (4)	C15—H15A	0.9700
C1—N1	1.416 (3)	C15—H15B	0.9700
C1—C10	1.437 (3)	C16—H16A	0.9600
C2—C3	1.397 (4)	C16—H16B	0.9600
C2—H2	0.9300	C16—H16C	0.9600
C3—C4	1.357 (3)	C17—N2	1.450 (3)
C3—H3	0.9300	C17—C18	1.506 (3)
C4—C5	1.414 (3)	C17—H17A	0.9700
C4—H4	0.9300	C17—H17B	0.9700
C5—C10	1.426 (3)	C18—O5	1.188 (3)
C5—C6	1.431 (3)	C18—O6	1.319 (3)
C6—C7	1.369 (3)	C19—O6	1.509 (7)
C6—S1	1.777 (2)	C19—C20	1.510 (8)
C7—C8	1.394 (3)	C19—H19A	0.9700
C7—H7	0.9300	C19—H19B	0.9700
C8—C9	1.358 (3)	C20—H20A	0.9600
C8—H8	0.9300	C20—H20B	0.9600
C9—C10	1.412 (3)	C20—H20C	0.9600
C9—H9	0.9300	C15'—O4	1.477 (10)
C11—N1	1.447 (4)	C15'—C16'	1.529 (10)
C11—H11A	0.9600	C15'—H15C	0.9700
C11—H11B	0.9600	C15'—H15D	0.9700
C11—H11C	0.9600	C16'—H16D	0.9600
C12—N1	1.472 (3)	C16'—H16E	0.9600
C12—H12A	0.9600	C16'—H16F	0.9600
C12—H12B	0.9600	C19'—O6	1.444 (8)
C12—H12C	0.9600	C19'—C20'	1.511 (8)
C13—N2	1.453 (3)	C19'—H19C	0.9700
C13—C14	1.506 (3)	C19'—H19D	0.9700
C13—H13A	0.9700	C20'—H20D	0.9600
C13—H13B	0.9700	C20'—H20E	0.9600
C14—O3	1.184 (3)	C20'—H20F	0.9600
C14—O4	1.314 (3)	N2—S1	1.6160 (18)
C15—O4	1.460 (5)	O1—S1	1.4295 (17)
C15—C16	1.478 (7)	O2—S1	1.4292 (15)
C2—C1—N1	123.0 (2)	H15A—C15—H15B	108.6
C2—C1—C10	118.9 (2)	N2—C17—C18	112.89 (18)
N1—C1—C10	118.0 (2)	N2—C17—H17A	109.0
C1—C2—C3	121.2 (2)	C18—C17—H17A	109.0
C1—C2—H2	119.4	N2—C17—H17B	109.0
C3—C2—H2	119.4	C18—C17—H17B	109.0
C4—C3—C2	121.4 (2)	H17A—C17—H17B	107.8
C4—C3—H3	119.3	O5—C18—O6	125.1 (2)
C2—C3—H3	119.3	O5—C18—C17	125.7 (2)
C3—C4—C5	120.2 (2)	O6—C18—C17	109.14 (19)
C3—C4—H4	119.9	O6—C19—C20	106.4 (6)
C5—C4—H4	119.9	O6—C19—H19A	110.4
C4—C5—C10	118.66 (19)	C20—C19—H19A	110.4
C4—C5—C6	124.39 (19)	O6—C19—H19B	110.4
C10—C5—C6	116.92 (18)	C20—C19—H19B	110.4
C7—C6—C5	121.96 (18)	H19A—C19—H19B	108.6
C7—C6—S1	116.10 (15)	O4—C15'—C16'	106.3 (13)
C5—C6—S1	121.85 (15)	O4—C15'—H15C	110.5
C6—C7—C8	119.89 (19)	C16'—C15'—H15C	110.5
C6—C7—H7	120.1	O4—C15'—H15D	110.5
C8—C7—H7	120.1	C16'—C15'—H15D	110.5
C9—C8—C7	120.3 (2)	H15C—C15'—H15D	108.7
C9—C8—H8	119.9	C15'—C16'—H16D	109.5
C7—C8—H8	119.9	C15'—C16'—H16E	109.5
C8—C9—C10	121.7 (2)	H16D—C16'—H16E	109.5
C8—C9—H9	119.1	C15'—C16'—H16F	109.5
C10—C9—H9	119.1	H16D—C16'—H16F	109.5
C9—C10—C5	119.07 (18)	H16E—C16'—H16F	109.5
C9—C10—C1	121.5 (2)	O6—C19'—C20'	102.3 (6)
C5—C10—C1	119.39 (19)	O6—C19'—H19C	111.3
N1—C11—H11A	109.5	C20'—C19'—H19C	111.3
N1—C11—H11B	109.5	O6—C19'—H19D	111.3
H11A—C11—H11B	109.5	C20'—C19'—H19D	111.3
N1—C11—H11C	109.5	H19C—C19'—H19D	109.2
H11A—C11—H11C	109.5	C19'—C20'—H20D	109.5
H11B—C11—H11C	109.5	C19'—C20'—H20E	109.5
N1—C12—H12A	109.5	H20D—C20'—H20E	109.5
N1—C12—H12B	109.5	C19'—C20'—H20F	109.5
H12A—C12—H12B	109.5	H20D—C20'—H20F	109.5
N1—C12—H12C	109.5	H20E—C20'—H20F	109.5
H12A—C12—H12C	109.5	C1—N1—C11	114.8 (2)
H12B—C12—H12C	109.5	C1—N1—C12	115.4 (2)
N2—C13—C14	112.71 (18)	C11—N1—C12	110.7 (2)
N2—C13—H13A	109.0	C17—N2—C13	119.76 (18)
C14—C13—H13A	109.0	C17—N2—S1	121.31 (15)
N2—C13—H13B	109.0	C13—N2—S1	118.44 (14)
C14—C13—H13B	109.0	C14—O4—C15	120.0 (4)
H13A—C13—H13B	107.8	C14—O4—C15'	105.2 (9)
O3—C14—O4	124.8 (2)	C18—O6—C19'	123.6 (6)
O3—C14—C13	125.6 (2)	C18—O6—C19	111.1 (4)
O4—C14—C13	109.5 (2)	O2—S1—O1	118.12 (10)
O4—C15—C16	107.0 (4)	O2—S1—N2	109.44 (10)
O4—C15—H15A	110.3	O1—S1—N2	106.18 (9)
C16—C15—H15A	110.3	O2—S1—C6	106.70 (9)
O4—C15—H15B	110.3	O1—S1—C6	111.09 (10)
C16—C15—H15B	110.3	N2—S1—C6	104.51 (9)
N1—C1—C2—C3	179.8 (2)	C18—C17—N2—C13	88.7 (2)
C10—C1—C2—C3	2.7 (4)	C18—C17—N2—S1	−83.1 (2)
C1—C2—C3—C4	0.7 (4)	C14—C13—N2—C17	81.6 (2)
C2—C3—C4—C5	−2.2 (4)	C14—C13—N2—S1	−106.41 (19)
C3—C4—C5—C10	0.2 (4)	O3—C14—O4—C15	8.1 (5)
C3—C4—C5—C6	−177.7 (2)	C13—C14—O4—C15	−172.2 (3)
C4—C5—C6—C7	175.7 (2)	O3—C14—O4—C15'	26 (2)
C10—C5—C6—C7	−2.3 (3)	C13—C14—O4—C15'	−155 (2)
C4—C5—C6—S1	−0.8 (3)	C16—C15—O4—C14	90.1 (10)
C10—C5—C6—S1	−178.75 (15)	C16—C15—O4—C15'	39 (4)
C5—C6—C7—C8	−1.0 (3)	C16'—C15'—O4—C14	163 (3)
S1—C6—C7—C8	175.69 (17)	C16'—C15'—O4—C15	−62 (3)
C6—C7—C8—C9	2.2 (3)	O5—C18—O6—C19'	−9.6 (5)
C7—C8—C9—C10	−0.2 (4)	C17—C18—O6—C19'	170.0 (4)
C8—C9—C10—C5	−3.2 (3)	O5—C18—O6—C19	11.4 (6)
C8—C9—C10—C1	179.9 (2)	C17—C18—O6—C19	−169.0 (6)
C4—C5—C10—C9	−173.8 (2)	C20'—C19'—O6—C18	95.9 (12)
C6—C5—C10—C9	4.3 (3)	C20'—C19'—O6—C19	34.6 (15)
C4—C5—C10—C1	3.2 (3)	C20—C19—O6—C18	159.6 (9)
C6—C5—C10—C1	−178.75 (18)	C20—C19—O6—C19'	−72.0 (19)
C2—C1—C10—C9	172.3 (2)	C17—N2—S1—O2	126.11 (17)
N1—C1—C10—C9	−4.9 (3)	C13—N2—S1—O2	−45.80 (18)
C2—C1—C10—C5	−4.6 (3)	C17—N2—S1—O1	−2.41 (19)
N1—C1—C10—C5	178.17 (19)	C13—N2—S1—O1	−174.32 (15)
N2—C13—C14—O3	−10.0 (4)	C17—N2—S1—C6	−119.93 (17)
N2—C13—C14—O4	170.3 (2)	C13—N2—S1—C6	68.16 (17)
N2—C17—C18—O5	−10.7 (3)	C7—C6—S1—O2	14.37 (19)
N2—C17—C18—O6	169.75 (19)	C5—C6—S1—O2	−168.98 (16)
C2—C1—N1—C11	111.9 (3)	C7—C6—S1—O1	144.39 (16)
C10—C1—N1—C11	−71.0 (3)	C5—C6—S1—O1	−38.95 (19)
C2—C1—N1—C12	−18.7 (4)	C7—C6—S1—N2	−101.51 (17)
C10—C1—N1—C12	158.4 (2)	C5—C6—S1—N2	75.14 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O1	0.93	2.36	3.006 (3)	126
C13—H13A···O2i	0.97	2.36	3.272 (3)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O1	0.93	2.36	3.006 (3)	126
C13—H13A⋯O2i	0.97	2.36	3.272 (3)	157

Symmetry code: (i) .