1-(2-Oxoindolin-3-yl-idene)-4-[2-(trifluoro-meth-oxy)phen-yl]thio-semi-carbazide.

The crystal structure of the title compound, C(16)H(11)F(3)N(4)O(2)S, is stabilized in the form of polymeric chains by N-H⋯O inter-actions. In the mol-ecular structure, two S(5) ring motifs are formed by intra-molecular N-H⋯N and N-H⋯O hydrogen bonding and two S(6) rings are present due to N-H⋯O and C-H⋯S inter-actions. π-π inter-actions are present with distances of 3.2735 (17), 3.563 (2) and 3.664 (4)/3.688 (3) Å between the centroids of the heterocyclic rings, between the centroids of the heterocyclic ring and trifluoro-meth-oxy-substituted phenyl ring, and between the centroids of the trifluoro-meth-oxy-substituted phenyl rings, respectively. The trifluoro-meth-oxy-phenyl group is disordered over two sites with an occupancy ratio of 0.642 (10):0.358 (10).

Related literature

For our work on the synthesis of biologically important isatin (systematic name 1H-indole-2,3-dione) derivatives, see: Pervez et al. (2007 ▶, 2008 ▶, 2009 ▶). For a related structure, see: Pervez et al. (2010 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C16H11F3N4O2S

M = 380.35

Tetragonal,

a = 13.4746 (8) Å

c = 18.1073 (10) Å

V = 3287.7 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.25 mm−1

T = 296 K

0.32 × 0.24 × 0.22 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.937, T max = 0.951

15673 measured reflections

4051 independent reflections

2321 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.069

wR(F 2) = 0.202

S = 1.04

4051 reflections

242 parameters

46 restraints

H-atom parameters constrained

Δρmax = 0.62 e Å−3

Δρmin = −0.39 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810034148/bq2229sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810034148/bq2229Isup2.hkl

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

C16H11F3N4O2S	Dx = 1.537 Mg m−3
Mr = 380.35	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P42/n	Cell parameters from 2321 reflections
Hall symbol: -P 4bc	θ = 3.1–28.3°
a = 13.4746 (8) Å	µ = 0.25 mm−1
c = 18.1073 (10) Å	T = 296 K
V = 3287.7 (3) Å3	Prism, yellow
Z = 8	0.32 × 0.24 × 0.22 mm
F(000) = 1552

Bruker Kappa APEXII CCD diffractometer	4051 independent reflections
Radiation source: fine-focus sealed tube	2321 reflections with I > 2σ(I)
graphite	Rint = 0.030
Detector resolution: 7.50 pixels mm-1	θmax = 28.3°, θmin = 3.1°
ω scans	h = −17→16
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −16→13
Tmin = 0.937, Tmax = 0.951	l = −24→18
15673 measured reflections

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)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.202	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0768P)2 + 2.277P] where P = (Fo2 + 2Fc2)/3
4051 reflections	(Δ/σ)max < 0.001
242 parameters	Δρmax = 0.62 e Å−3
46 restraints	Δρmin = −0.39 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)
S1	0.12312 (12)	−0.17880 (9)	−0.07998 (6)	0.1023 (5)
O1	0.13028 (17)	0.12230 (19)	−0.19341 (11)	0.0617 (6)
O2A	0.1645 (8)	−0.0082 (5)	0.1781 (4)	0.098 (3)	0.642 (10)
C16A	0.1209 (8)	0.0557 (10)	0.2175 (6)	0.110 (3)	0.642 (10)
F1A	0.1590 (10)	0.1485 (9)	0.2063 (6)	0.142 (4)	0.642 (10)
F2A	0.0226 (6)	0.0520 (8)	0.2108 (9)	0.256 (8)	0.642 (10)
F3A	0.1494 (6)	0.0461 (6)	0.2903 (2)	0.143 (3)	0.642 (10)
O2B	0.1302 (18)	0.0168 (10)	0.1743 (8)	0.146 (9)	0.358 (10)
C16B	0.1390 (16)	0.0527 (18)	0.2389 (9)	0.110 (3)	0.358 (10)
F1B	0.1175 (18)	0.1457 (16)	0.2154 (13)	0.155 (9)	0.358 (10)
F2B	0.230 (2)	0.0142 (14)	0.246 (2)	0.42 (2)	0.358 (10)
F3B	0.0538 (17)	0.0320 (11)	0.2705 (9)	0.184 (9)	0.358 (10)
C1	0.1288 (2)	0.1907 (3)	−0.14785 (15)	0.0506 (7)
C2	0.1252 (2)	0.1801 (2)	−0.06543 (13)	0.0452 (7)
C3	0.1269 (2)	0.2802 (2)	−0.03581 (15)	0.0471 (7)
C4	0.1262 (2)	0.3187 (3)	0.03511 (17)	0.0596 (8)
H4	0.1239	0.2771	0.0761	0.071*
C5	0.1289 (3)	0.4203 (3)	0.0433 (2)	0.0715 (10)
H5	0.1288	0.4474	0.0905	0.086*
C6	0.1319 (3)	0.4826 (3)	−0.0170 (2)	0.0729 (10)
H6	0.1332	0.5509	−0.0095	0.087*
C7	0.1330 (3)	0.4460 (3)	−0.0883 (2)	0.0639 (9)
H7	0.1351	0.4881	−0.1290	0.077*
C8	0.1307 (2)	0.3447 (3)	−0.09654 (16)	0.0516 (7)
C9	0.1229 (2)	−0.0776 (2)	−0.02940 (17)	0.0537 (7)
C10A	0.1224 (4)	−0.1399 (3)	0.0985 (2)	0.0673 (11)	0.642 (10)
C11A	0.1162 (5)	−0.2412 (3)	0.0844 (2)	0.0673 (11)	0.642 (10)
H11A	0.1136	−0.2640	0.0360	0.081*	0.642 (10)
C12A	0.1139 (4)	−0.3082 (3)	0.1428 (3)	0.0673 (11)	0.642 (10)
H12A	0.1098	−0.3759	0.1333	0.081*	0.642 (10)
C13A	0.1178 (3)	−0.2740 (4)	0.2151 (2)	0.0673 (11)	0.642 (10)
H13A	0.1163	−0.3189	0.2541	0.081*	0.642 (10)
C14A	0.1240 (4)	−0.1728 (4)	0.22919 (19)	0.0673 (11)	0.642 (10)
H14A	0.1266	−0.1500	0.2776	0.081*	0.642 (10)
C15A	0.1263 (4)	−0.1058 (3)	0.1709 (3)	0.0673 (11)	0.642 (10)
C10B	0.1284 (4)	−0.1331 (4)	0.1078 (3)	0.0557 (16)	0.358 (10)
C11B	0.1090 (6)	−0.2343 (4)	0.1039 (4)	0.0557 (16)	0.358 (10)
H11B	0.0957	−0.2637	0.0585	0.067*	0.358 (10)
C12B	0.1096 (6)	−0.2914 (5)	0.1678 (5)	0.0557 (16)	0.358 (10)
H12B	0.0967	−0.3591	0.1652	0.067*	0.358 (10)
C13B	0.1296 (5)	−0.2474 (6)	0.2356 (4)	0.0557 (16)	0.358 (10)
H13B	0.1300	−0.2856	0.2784	0.067*	0.358 (10)
C14B	0.1490 (6)	−0.1462 (6)	0.2395 (3)	0.0557 (16)	0.358 (10)
H14B	0.1623	−0.1167	0.2849	0.067*	0.358 (10)
C15B	0.1484 (5)	−0.0890 (5)	0.1756 (3)	0.0557 (16)	0.358 (10)
N1	0.13202 (18)	0.2883 (2)	−0.16207 (12)	0.0553 (7)
H1	0.1345	0.3134	−0.2057	0.066*
N2	0.12204 (17)	0.09849 (19)	−0.02780 (12)	0.0475 (6)
N3	0.12066 (19)	0.0127 (2)	−0.06555 (13)	0.0528 (7)
H3	0.1184	0.0140	−0.1130	0.063*
N4	0.12473 (19)	−0.0670 (2)	0.04415 (13)	0.0553 (7)
H4A	0.1278	−0.0069	0.0599	0.066*

	U11	U22	U33	U12	U13	U23
S1	0.1630 (13)	0.0717 (7)	0.0722 (7)	−0.0081 (7)	0.0368 (7)	−0.0177 (5)
O1	0.0676 (15)	0.0853 (16)	0.0323 (10)	−0.0031 (12)	0.0074 (9)	−0.0023 (10)
O2A	0.190 (8)	0.054 (4)	0.051 (3)	0.024 (4)	0.019 (4)	0.005 (3)
C16A	0.151 (8)	0.120 (6)	0.060 (6)	−0.030 (5)	−0.059 (5)	−0.016 (5)
F1A	0.180 (11)	0.123 (6)	0.123 (7)	−0.011 (6)	−0.038 (7)	−0.019 (4)
F2A	0.109 (5)	0.203 (10)	0.457 (19)	0.043 (5)	−0.092 (9)	−0.163 (12)
F3A	0.179 (7)	0.215 (7)	0.034 (2)	−0.028 (6)	−0.003 (3)	−0.027 (3)
O2B	0.33 (2)	0.069 (7)	0.044 (5)	0.121 (10)	0.026 (8)	0.004 (4)
C16B	0.151 (8)	0.120 (6)	0.060 (6)	−0.030 (5)	−0.059 (5)	−0.016 (5)
F1B	0.19 (2)	0.112 (10)	0.159 (12)	−0.054 (10)	0.060 (12)	−0.080 (9)
F2B	0.42 (4)	0.170 (16)	0.69 (5)	−0.075 (19)	−0.42 (4)	0.02 (2)
F3B	0.25 (2)	0.151 (10)	0.152 (13)	0.005 (14)	0.136 (15)	−0.024 (10)
C1	0.0423 (16)	0.078 (2)	0.0314 (13)	0.0001 (14)	0.0041 (11)	0.0070 (14)
C2	0.0400 (15)	0.0660 (19)	0.0296 (12)	−0.0008 (13)	0.0025 (10)	0.0047 (12)
C3	0.0425 (15)	0.0615 (18)	0.0374 (14)	0.0019 (13)	0.0042 (11)	0.0062 (12)
C4	0.068 (2)	0.069 (2)	0.0415 (16)	0.0017 (17)	0.0063 (14)	0.0006 (14)
C5	0.085 (3)	0.071 (2)	0.059 (2)	0.0015 (19)	0.0102 (18)	−0.0106 (17)
C6	0.073 (2)	0.064 (2)	0.082 (3)	0.0055 (18)	0.0098 (19)	−0.0010 (19)
C7	0.059 (2)	0.063 (2)	0.070 (2)	0.0048 (16)	0.0044 (16)	0.0183 (17)
C8	0.0412 (16)	0.071 (2)	0.0429 (15)	0.0018 (14)	0.0043 (12)	0.0121 (13)
C9	0.0481 (17)	0.064 (2)	0.0486 (16)	−0.0024 (14)	0.0112 (13)	−0.0015 (14)
C10A	0.0693 (19)	0.073 (2)	0.0594 (17)	−0.0060 (14)	0.0037 (13)	0.0070 (12)
C11A	0.0693 (19)	0.073 (2)	0.0594 (17)	−0.0060 (14)	0.0037 (13)	0.0070 (12)
C12A	0.0693 (19)	0.073 (2)	0.0594 (17)	−0.0060 (14)	0.0037 (13)	0.0070 (12)
C13A	0.0693 (19)	0.073 (2)	0.0594 (17)	−0.0060 (14)	0.0037 (13)	0.0070 (12)
C14A	0.0693 (19)	0.073 (2)	0.0594 (17)	−0.0060 (14)	0.0037 (13)	0.0070 (12)
C15A	0.0693 (19)	0.073 (2)	0.0594 (17)	−0.0060 (14)	0.0037 (13)	0.0070 (12)
C10B	0.050 (3)	0.072 (3)	0.045 (2)	0.003 (2)	0.0068 (18)	0.020 (2)
C11B	0.050 (3)	0.072 (3)	0.045 (2)	0.003 (2)	0.0068 (18)	0.020 (2)
C12B	0.050 (3)	0.072 (3)	0.045 (2)	0.003 (2)	0.0068 (18)	0.020 (2)
C13B	0.050 (3)	0.072 (3)	0.045 (2)	0.003 (2)	0.0068 (18)	0.020 (2)
C14B	0.050 (3)	0.072 (3)	0.045 (2)	0.003 (2)	0.0068 (18)	0.020 (2)
C15B	0.050 (3)	0.072 (3)	0.045 (2)	0.003 (2)	0.0068 (18)	0.020 (2)
N1	0.0531 (15)	0.0783 (19)	0.0344 (12)	0.0027 (13)	0.0047 (10)	0.0154 (12)
N2	0.0452 (13)	0.0629 (16)	0.0345 (12)	−0.0010 (11)	0.0049 (9)	0.0009 (11)
N3	0.0606 (16)	0.0635 (17)	0.0342 (12)	−0.0020 (12)	0.0057 (10)	−0.0019 (11)
N4	0.0656 (17)	0.0577 (16)	0.0427 (13)	−0.0005 (13)	0.0059 (11)	0.0042 (11)

S1—C9	1.643 (3)	C9—N3	1.382 (4)
O1—C1	1.237 (4)	C10A—C11A	1.3900
O2A—C16A	1.263 (12)	C10A—C15A	1.3900
O2A—C15A	1.418 (8)	C10A—N4	1.391 (4)
C16A—F2A	1.331 (12)	C11A—C12A	1.3900
C16A—F1A	1.367 (13)	C11A—H11A	0.9300
C16A—F3A	1.380 (9)	C12A—C13A	1.3900
O2B—C16B	1.271 (17)	C12A—H12A	0.9300
O2B—C15B	1.448 (11)	C13A—C14A	1.3900
C16B—F3B	1.314 (19)	C13A—H13A	0.9300
C16B—F2B	1.337 (19)	C14A—C15A	1.3900
C16B—F1B	1.35 (2)	C14A—H14A	0.9300
C1—N1	1.342 (4)	C10B—C11B	1.3900
C1—C2	1.500 (4)	C10B—C15B	1.3900
C2—N2	1.295 (4)	C10B—N4	1.457 (4)
C2—C3	1.452 (4)	C11B—C12B	1.3900
C3—C4	1.385 (4)	C11B—H11B	0.9300
C3—C8	1.403 (4)	C12B—C13B	1.3900
C4—C5	1.377 (5)	C12B—H12B	0.9300
C4—H4	0.9300	C13B—C14B	1.3900
C5—C6	1.378 (5)	C13B—H13B	0.9300
C5—H5	0.9300	C14B—C15B	1.3900
C6—C7	1.383 (5)	C14B—H14B	0.9300
C6—H6	0.9300	N1—H1	0.8600
C7—C8	1.373 (5)	N2—N3	1.342 (3)
C7—H7	0.9300	N3—H3	0.8600
C8—N1	1.409 (4)	N4—H4A	0.8600
C9—N4	1.340 (4)
C16A—O2A—C15A	121.0 (9)	C10A—C11A—H11A	120.0
O2A—C16A—F2A	112.7 (9)	C12A—C11A—H11A	120.0
O2A—C16A—F1A	111.4 (11)	C13A—C12A—C11A	120.0
F2A—C16A—F1A	113.3 (11)	C13A—C12A—H12A	120.0
O2A—C16A—F3A	110.2 (10)	C11A—C12A—H12A	120.0
F2A—C16A—F3A	111.1 (10)	C12A—C13A—C14A	120.0
F1A—C16A—F3A	97.1 (9)	C12A—C13A—H13A	120.0
C16B—O2B—C15B	110.1 (16)	C14A—C13A—H13A	120.0
O2B—C16B—F3B	103.8 (18)	C13A—C14A—C15A	120.0
O2B—C16B—F2B	91.6 (18)	C13A—C14A—H14A	120.0
F3B—C16B—F2B	133 (3)	C15A—C14A—H14A	120.0
O2B—C16B—F1B	92.5 (15)	C14A—C15A—C10A	120.0
F3B—C16B—F1B	98 (2)	C14A—C15A—O2A	122.7 (4)
F2B—C16B—F1B	126 (2)	C10A—C15A—O2A	114.1 (5)
O1—C1—N1	127.0 (3)	C11B—C10B—C15B	120.0
O1—C1—C2	126.4 (3)	C11B—C10B—N4	123.6 (3)
N1—C1—C2	106.5 (3)	C15B—C10B—N4	116.4 (3)
N2—C2—C3	126.5 (2)	C12B—C11B—C10B	120.0
N2—C2—C1	127.2 (3)	C12B—C11B—H11B	120.0
C3—C2—C1	106.2 (2)	C10B—C11B—H11B	120.0
C4—C3—C8	119.7 (3)	C13B—C12B—C11B	120.0
C4—C3—C2	133.7 (3)	C13B—C12B—H12B	120.0
C8—C3—C2	106.6 (2)	C11B—C12B—H12B	120.0
C5—C4—C3	118.2 (3)	C12B—C13B—C14B	120.0
C5—C4—H4	120.9	C12B—C13B—H13B	120.0
C3—C4—H4	120.9	C14B—C13B—H13B	120.0
C4—C5—C6	121.4 (3)	C13B—C14B—C15B	120.0
C4—C5—H5	119.3	C13B—C14B—H14B	120.0
C6—C5—H5	119.3	C15B—C14B—H14B	120.0
C5—C6—C7	121.6 (4)	C14B—C15B—C10B	120.0
C5—C6—H6	119.2	C14B—C15B—O2B	124.1 (6)
C7—C6—H6	119.2	C10B—C15B—O2B	111.9 (7)
C8—C7—C6	117.1 (3)	C1—N1—C8	111.5 (2)
C8—C7—H7	121.5	C1—N1—H1	124.2
C6—C7—H7	121.5	C8—N1—H1	124.2
C7—C8—C3	122.1 (3)	C2—N2—N3	117.6 (2)
C7—C8—N1	128.8 (3)	N2—N3—C9	121.1 (2)
C3—C8—N1	109.1 (3)	N2—N3—H3	119.5
N4—C9—N3	112.2 (3)	C9—N3—H3	119.5
N4—C9—S1	130.0 (3)	C9—N4—C10A	128.9 (3)
N3—C9—S1	117.8 (2)	C9—N4—C10B	136.2 (4)
C11A—C10A—C15A	120.0	C10A—N4—C10B	8.0 (4)
C11A—C10A—N4	124.4 (3)	C9—N4—H4A	115.6
C15A—C10A—N4	115.6 (3)	C10A—N4—H4A	115.6
C10A—C11A—C12A	120.0	C10B—N4—H4A	108.1
C15A—O2A—C16A—F2A	−40.2 (14)	C16A—O2A—C15A—C14A	−67.6 (12)
C15A—O2A—C16A—F1A	−168.9 (7)	C16A—O2A—C15A—C10A	132.6 (8)
C15A—O2A—C16A—F3A	84.6 (12)	C15B—C10B—C11B—C12B	0.0
C15B—O2B—C16B—F3B	−80 (2)	N4—C10B—C11B—C12B	−177.1 (2)
C15B—O2B—C16B—F2B	54 (2)	C10B—C11B—C12B—C13B	0.0
C15B—O2B—C16B—F1B	−179.8 (18)	C11B—C12B—C13B—C14B	0.0
O1—C1—C2—N2	−0.7 (5)	C12B—C13B—C14B—C15B	0.0
N1—C1—C2—N2	−179.6 (3)	C13B—C14B—C15B—C10B	0.0
O1—C1—C2—C3	178.8 (3)	C13B—C14B—C15B—O2B	155.7 (14)
N1—C1—C2—C3	−0.1 (3)	C11B—C10B—C15B—C14B	0.0
N2—C2—C3—C4	0.4 (5)	N4—C10B—C15B—C14B	177.3 (2)
C1—C2—C3—C4	−179.2 (3)	C11B—C10B—C15B—O2B	−158.5 (12)
N2—C2—C3—C8	179.8 (3)	N4—C10B—C15B—O2B	18.8 (12)
C1—C2—C3—C8	0.2 (3)	C16B—O2B—C15B—C14B	16 (3)
C8—C3—C4—C5	0.3 (5)	C16B—O2B—C15B—C10B	173.1 (16)
C2—C3—C4—C5	179.6 (3)	O1—C1—N1—C8	−179.0 (3)
C3—C4—C5—C6	0.3 (5)	C2—C1—N1—C8	−0.1 (3)
C4—C5—C6—C7	−0.5 (6)	C7—C8—N1—C1	−179.9 (3)
C5—C6—C7—C8	0.2 (5)	C3—C8—N1—C1	0.3 (3)
C6—C7—C8—C3	0.4 (5)	C3—C2—N2—N3	179.8 (3)
C6—C7—C8—N1	−179.4 (3)	C1—C2—N2—N3	−0.8 (4)
C4—C3—C8—C7	−0.6 (4)	C2—N2—N3—C9	176.3 (3)
C2—C3—C8—C7	179.9 (3)	N4—C9—N3—N2	1.1 (4)
C4—C3—C8—N1	179.2 (3)	S1—C9—N3—N2	−178.9 (2)
C2—C3—C8—N1	−0.3 (3)	N3—C9—N4—C10A	176.6 (3)
C15A—C10A—C11A—C12A	0.0	S1—C9—N4—C10A	−3.5 (5)
N4—C10A—C11A—C12A	−179.7 (4)	N3—C9—N4—C10B	−179.2 (4)
C10A—C11A—C12A—C13A	0.0	S1—C9—N4—C10B	0.7 (6)
C11A—C12A—C13A—C14A	0.0	C11A—C10A—N4—C9	−0.9 (5)
C12A—C13A—C14A—C15A	0.0	C15A—C10A—N4—C9	179.4 (3)
C13A—C14A—C15A—C10A	0.0	C11A—C10A—N4—C10B	−159 (3)
C13A—C14A—C15A—O2A	−158.6 (7)	C15A—C10A—N4—C10B	21 (2)
C11A—C10A—C15A—C14A	0.0	C11B—C10B—N4—C9	−14.8 (5)
N4—C10A—C15A—C14A	179.8 (4)	C15B—C10B—N4—C9	168.0 (4)
C11A—C10A—C15A—O2A	160.3 (6)	C11B—C10B—N4—C10A	10 (2)
N4—C10A—C15A—O2A	−19.9 (6)	C15B—C10B—N4—C10A	−168 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.86	1.99	2.841 (3)	173
N3—H3···O1	0.86	2.07	2.748 (3)	136
N4—H4A···O2A	0.86	2.20	2.607 (8)	109
N4—H4A···N2	0.86	2.13	2.583 (4)	112
C11A—H11A···S1	0.93	2.40	3.096 (4)	132

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.86	1.99	2.841 (3)	173
N3—H3⋯O1	0.86	2.07	2.748 (3)	136
N4—H4A⋯O2A	0.86	2.20	2.607 (8)	109
N4—H4A⋯N2	0.86	2.13	2.583 (4)	112
C11A—H11A⋯S1	0.93	2.40	3.096 (4)	132

Symmetry code: (i) .