(1Z)-1-(4-Methoxy­phen­yl)ethan-1-one thio­semicarbazone

Geometric parameters of the title compound, C₁₀H₁₃N₃OS, are in the usual ranges. There are two similar mol­ecules (r.m.s. deviation 0.131 Å for all non-H atoms) in the asymmetric unit. The crystal packing is characterized by sheets in the (202) plane. The mol­ecules in the sheets are connected by N—H...O and N—H...S hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.008 Å
• R factor = 0.079
• wR factor = 0.240
• Data-to-parameter ratio = 15.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.24 Ratio

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.55 Ratio
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          8
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          5

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

Thiourea and its derivatives have been the focus of attention in recent years in view of their interesting physicochemical properties and broad range of applications in several chemical disciplines. Certain thiourea molecules have antiviral activity and might be characterized as prospective inhibitors of many enzymes, particularly, HIV-1 reverse transcriptase (Ren et al., 2000; Onderwater et al., 2004). As antibacterial and antifungal agents, they have been used in agriculture (Rodriguez-Fernandez et al., 2005). In technical applications, dithioamide compounds are known to be prospective nonlinear optical materials (Zhou et al., 2003), corrosion inhibitors for copper and iron in acidic media (Stankovic & Vukovic 1996) and functionalization agents for production of chemically modified resins (Trochimczuk & Kolarz 2000). Thiourea derivatives have been also reported as potential receptors and ionophores for heavy metal cations (Castro et al., 2003), building blocks in the synthesis of heterocyclic compounds (Kearney et al., 1998). Finally, the strong hydrogen-bonding donor capability of the –N(H)—C(=S)—N(H)- group has been widely exploited in supramolecular chemistry, where it has been used as a building block for anion receptors (Nie et al., 2004). The crystal structures of 1-(2-bromo-5-methoxybenzoyl)thiosemicarbazide, (Sarojini et al., 2007), salicylaldehyde thiosemicarbazone (Chattopadhyay et al., 1988), 4-(methylsulfanyl)benzaldehyde thiosemicarbazone (Yathirajan et al., 2006) and benzoin thiosemicarbazone (Dinçer et al., 2005) A new carbothioamide, (I), C₁₀H₁₃N₃OS, has been synthesized and its crystal structure is reported.

Geometric parameters of the title compound are in the usual ranges. There are two similar (r.m.s. deviation 0.131 Å for all non-H atoms) molecules in the asymmetric unit. The crystal packing is characterized by sheets in the (202) plane. The molecules in a sheet are connected by N—H···O and N—H···S hydrogen bonds.

Related literature

For related literature, see: Castro et al. (2003); Chattopadhyay et al. (1988); Dinçer et al. (2005); Kearney et al. (1998); Nie et al. (2004); Onderwater et al. (2004); Ren et al. (2000); Rodriguez-Fernandez et al. (2005); Sarojini et al. (2007); Stankovic & Vukovic (1996); Trochimczuk & Kolarz (2000); Yathirajan et al. (2006); Zhou et al. (2003).

S2. Experimental

A mixture of 1-(4-methoxyphenyl)ethanone (1.5 g, 0.01 mol) and hydrazinecarbothioamide (0.91 g, 0.01 mol) in 15 ml of absolute ethanol containing 2 drops of 4 M sulfuric acid was refluxed for about 3 h. On cooling, the solid separated was filtered and recrystallized from ethyl acetate (m.p.: 448–450 K). Analysis found: C 53.70, H 5.83, N 18.76, S 14.31%; C₁₀H₁₃N₃OS requires: C 53.79, H 5.87, N 18.82, S 14.36%.

S3. Refinement

H atoms were found in a difference map, but they were geometrically positioned and refined with fixed individual displacement parameters [U(H) = 1.2 U_eq(C) or U(H) = 1.5 U_eq(C_methyl)] using a riding model with C_aromatic—H = 0.95 Å, C_methyl—H = 0.98 Å and N—H = 0.88 Å The methyl groups were allowed to rotate but not to tip. The crystal was a non-merohedral twin (twin law -1 0 0/0 - 1 0/0.85 0 1) with a contribution of 66.3 (3)% of the main component.

Computing details

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures

	Fig. 1. Perspective view of the title compound with the atom numbering; displacement ellipsoids are at the 50% probability level.
	Fig. 2. Partial packing diagram of the title compound. View onto the (202) plane. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding are omitted.

(1Z)-1-(4-Methoxyphenyl)ethan-1-one thiosemicarbazone

Crystal data

C10H13N3OS	F(000) = 944
Mr = 223.29	Dx = 1.315 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.3548 (9) Å	Cell parameters from 30258 reflections
b = 8.4141 (5) Å	θ = 2.8–26.2°
c = 19.6562 (13) Å	µ = 0.27 mm^−1
β = 108.123 (5)°	T = 173 K
V = 2256.4 (3) Å^3	Plate, yellow
Z = 8	0.31 × 0.25 × 0.18 mm

Data collection

Stoe IPDSII two-circle diffractometer	4478 independent reflections
Radiation source: fine-focus sealed tube	3571 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.082
ω scans	θmax = 26.3°, θmin = 2.7°
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995)	h = −17→16
Tmin = 0.923, Tmax = 0.954	k = −10→10
42568 measured reflections	l = −12→24

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.079	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.240	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.1562P)^2 + 4.346P] where P = (Fo^2 + 2Fc^2)/3
4478 reflections	(Δ/σ)max = 0.001
282 parameters	Δρmax = 0.79 e Å^−3
0 restraints	Δρmin = −0.48 e Å^−3

Special details

Experimental. ;

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.48440 (11)	0.23608 (16)	0.76976 (8)	0.0341 (4)
O1	0.8050 (3)	0.0042 (5)	0.38379 (19)	0.0334 (9)
N1	0.6287 (3)	0.1143 (5)	0.6373 (2)	0.0310 (10)
N2	0.5907 (3)	0.1107 (5)	0.6946 (2)	0.0297 (10)
H2	0.5967	0.0253	0.7215	0.036*
N3	0.5500 (3)	0.3732 (5)	0.6715 (2)	0.0304 (10)
H3A	0.5826	0.3733	0.6403	0.036*
H3B	0.5206	0.4603	0.6789	0.036*
C1	0.6949 (4)	0.0096 (6)	0.6359 (3)	0.0247 (10)
C2	0.7407 (4)	−0.1069 (8)	0.6946 (3)	0.0395 (13)
H2A	0.7371	−0.0650	0.7402	0.06 (2)*
H2B	0.8095	−0.1235	0.6977	0.07 (2)*
H2C	0.7055	−0.2082	0.6842	0.14 (5)*
C3	0.5450 (4)	0.2403 (6)	0.7077 (3)	0.0266 (10)
C11	0.7240 (4)	0.0096 (6)	0.5701 (3)	0.0258 (10)
C12	0.6569 (4)	0.0578 (6)	0.5050 (3)	0.0274 (10)
H12	0.5933	0.0912	0.5041	0.033*
C13	0.6808 (4)	0.0583 (6)	0.4416 (3)	0.0290 (11)
H13	0.6342	0.0910	0.3980	0.035*
C14	0.7742 (4)	0.0099 (6)	0.4433 (3)	0.0277 (11)
C15	0.8419 (4)	−0.0382 (7)	0.5070 (3)	0.0302 (11)
H15	0.9055	−0.0709	0.5077	0.036*
C16	0.8172 (4)	−0.0388 (7)	0.5697 (3)	0.0279 (11)
H16	0.8641	−0.0724	0.6131	0.033*
C17	0.7387 (4)	0.0625 (8)	0.3175 (3)	0.0409 (14)
H17A	0.6813	−0.0074	0.3019	0.061*
H17B	0.7720	0.0642	0.2809	0.061*
H17C	0.7176	0.1703	0.3246	0.061*
S1A	−0.04879 (11)	0.28900 (16)	0.75014 (8)	0.0352 (4)
O1A	0.3755 (3)	0.4380 (5)	0.42642 (19)	0.0332 (9)
N1A	0.1031 (3)	0.4094 (5)	0.6234 (2)	0.0281 (9)
N2A	0.0390 (3)	0.4199 (5)	0.6636 (2)	0.0260 (9)
H2N	0.0117	0.5106	0.6690	0.031*
N3A	0.0556 (4)	0.1494 (5)	0.6767 (2)	0.0339 (10)
H3A1	0.0897	0.1504	0.6464	0.041*
H3A2	0.0448	0.0590	0.6955	0.041*
C1A	0.1091 (4)	0.5312 (6)	0.5826 (3)	0.0264 (10)
C2A	0.0463 (4)	0.6765 (6)	0.5725 (3)	0.0310 (11)
H2A1	−0.0167	0.6492	0.5790	0.07 (2)*
H2A2	0.0351	0.7183	0.5240	0.07 (2)*
H2A3	0.0794	0.7572	0.6076	0.11 (4)*
C3A	0.0204 (4)	0.2839 (6)	0.6939 (2)	0.0247 (10)
C11A	0.1823 (4)	0.5119 (6)	0.5444 (3)	0.0254 (10)
C12A	0.2609 (4)	0.4073 (6)	0.5702 (3)	0.0292 (11)
H12A	0.2697	0.3540	0.6143	0.035*
C13A	0.3268 (4)	0.3796 (6)	0.5323 (3)	0.0294 (11)
H13A	0.3799	0.3081	0.5505	0.035*
C14A	0.3143 (4)	0.4573 (6)	0.4679 (3)	0.0266 (10)
C15A	0.2370 (4)	0.5645 (7)	0.4413 (3)	0.0297 (11)
H15A	0.2290	0.6181	0.3973	0.036*
C16A	0.1721 (4)	0.5919 (7)	0.4799 (3)	0.0296 (11)
H16A	0.1201	0.6658	0.4623	0.036*
C17A	0.4539 (4)	0.3252 (6)	0.4501 (3)	0.0322 (12)
H17D	0.4976	0.3570	0.4972	0.048*
H17E	0.4909	0.3221	0.4158	0.048*
H17F	0.4268	0.2197	0.4535	0.048*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0511 (8)	0.0239 (6)	0.0392 (7)	−0.0035 (6)	0.0314 (6)	−0.0025 (5)
O1	0.034 (2)	0.041 (2)	0.0301 (18)	0.0052 (16)	0.0170 (16)	0.0016 (16)
N1	0.039 (2)	0.028 (2)	0.032 (2)	−0.0009 (19)	0.020 (2)	−0.0008 (18)
N2	0.045 (3)	0.022 (2)	0.030 (2)	0.0007 (19)	0.023 (2)	0.0026 (17)
N3	0.043 (3)	0.028 (2)	0.027 (2)	0.001 (2)	0.022 (2)	−0.0018 (18)
C1	0.023 (2)	0.024 (2)	0.027 (2)	−0.0009 (19)	0.0091 (19)	0.0019 (19)
C2	0.042 (3)	0.049 (3)	0.029 (3)	0.014 (3)	0.012 (2)	0.009 (3)
C3	0.033 (3)	0.024 (2)	0.025 (2)	−0.006 (2)	0.013 (2)	−0.0031 (19)
C11	0.031 (3)	0.019 (2)	0.029 (2)	0.0030 (19)	0.012 (2)	0.0005 (19)
C12	0.025 (2)	0.029 (3)	0.029 (2)	0.005 (2)	0.010 (2)	0.002 (2)
C13	0.030 (3)	0.030 (3)	0.027 (2)	0.004 (2)	0.009 (2)	0.002 (2)
C14	0.034 (3)	0.025 (3)	0.029 (2)	0.000 (2)	0.016 (2)	0.000 (2)
C15	0.026 (3)	0.033 (3)	0.034 (3)	0.002 (2)	0.012 (2)	0.000 (2)
C16	0.023 (2)	0.033 (3)	0.027 (2)	0.006 (2)	0.007 (2)	0.004 (2)
C17	0.041 (3)	0.055 (4)	0.028 (3)	0.005 (3)	0.013 (2)	0.007 (3)
S1A	0.0495 (8)	0.0254 (6)	0.0436 (8)	−0.0024 (6)	0.0331 (7)	−0.0012 (5)
O1A	0.036 (2)	0.037 (2)	0.0314 (18)	0.0035 (17)	0.0180 (17)	0.0046 (16)
N1A	0.033 (2)	0.027 (2)	0.030 (2)	0.0015 (18)	0.0175 (19)	0.0035 (17)
N2A	0.035 (2)	0.0195 (19)	0.029 (2)	0.0019 (17)	0.0177 (19)	0.0037 (16)
N3A	0.051 (3)	0.023 (2)	0.037 (2)	−0.005 (2)	0.027 (2)	−0.0012 (19)
C1A	0.030 (3)	0.024 (2)	0.024 (2)	−0.001 (2)	0.007 (2)	−0.0010 (19)
C2A	0.040 (3)	0.025 (3)	0.035 (3)	0.005 (2)	0.021 (2)	0.003 (2)
C3A	0.029 (2)	0.022 (2)	0.024 (2)	−0.004 (2)	0.010 (2)	−0.0012 (18)
C11A	0.030 (3)	0.021 (2)	0.026 (2)	−0.0071 (19)	0.011 (2)	−0.0039 (18)
C12A	0.034 (3)	0.030 (3)	0.024 (2)	0.000 (2)	0.009 (2)	0.004 (2)
C13A	0.031 (3)	0.031 (3)	0.030 (2)	0.004 (2)	0.014 (2)	0.005 (2)
C14A	0.030 (3)	0.024 (2)	0.028 (2)	−0.003 (2)	0.013 (2)	−0.003 (2)
C15A	0.030 (3)	0.035 (3)	0.026 (2)	−0.004 (2)	0.012 (2)	0.001 (2)
C16A	0.031 (3)	0.030 (3)	0.029 (3)	−0.002 (2)	0.012 (2)	0.000 (2)
C17A	0.032 (3)	0.028 (3)	0.040 (3)	0.001 (2)	0.016 (2)	−0.001 (2)

Geometric parameters (Å, º)

S1—C3	1.704 (5)	S1A—C3A	1.701 (5)
O1—C14	1.374 (6)	O1A—C14A	1.381 (6)
O1—C17	1.439 (7)	O1A—C17A	1.434 (6)
N1—C1	1.302 (6)	N1A—C1A	1.320 (7)
N1—N2	1.398 (6)	N1A—N2A	1.389 (6)
N2—C3	1.338 (6)	N2A—C3A	1.354 (6)
N2—H2	0.8800	N2A—H2N	0.8800
N3—C3	1.339 (7)	N3A—C3A	1.326 (7)
N3—H3A	0.8800	N3A—H3A1	0.8800
N3—H3B	0.8800	N3A—H3A2	0.8800
C1—C11	1.478 (7)	C1A—C11A	1.478 (7)
C1—C2	1.500 (7)	C1A—C2A	1.495 (7)
C2—H2A	0.9800	C2A—H2A1	0.9800
C2—H2B	0.9800	C2A—H2A2	0.9800
C2—H2C	0.9800	C2A—H2A3	0.9800
C11—C12	1.401 (7)	C11A—C12A	1.397 (7)
C11—C16	1.401 (7)	C11A—C16A	1.402 (7)
C12—C13	1.391 (7)	C12A—C13A	1.393 (7)
C12—H12	0.9500	C12A—H12A	0.9500
C13—C14	1.391 (7)	C13A—C14A	1.387 (7)
C13—H13	0.9500	C13A—H13A	0.9500
C14—C15	1.386 (8)	C14A—C15A	1.398 (8)
C15—C16	1.384 (7)	C15A—C16A	1.393 (7)
C15—H15	0.9500	C15A—H15A	0.9500
C16—H16	0.9500	C16A—H16A	0.9500
C17—H17A	0.9800	C17A—H17D	0.9800
C17—H17B	0.9800	C17A—H17E	0.9800
C17—H17C	0.9800	C17A—H17F	0.9800
C14—O1—C17	117.4 (4)	C14A—O1A—C17A	117.7 (4)
C1—N1—N2	118.2 (4)	C1A—N1A—N2A	118.4 (4)
C3—N2—N1	118.4 (4)	C3A—N2A—N1A	116.9 (4)
C3—N2—H2	120.8	C3A—N2A—H2N	121.6
N1—N2—H2	120.8	N1A—N2A—H2N	121.6
C3—N3—H3A	120.0	C3A—N3A—H3A1	120.0
C3—N3—H3B	120.0	C3A—N3A—H3A2	120.0
H3A—N3—H3B	120.0	H3A1—N3A—H3A2	120.0
N1—C1—C11	115.1 (4)	N1A—C1A—C11A	114.5 (4)
N1—C1—C2	125.1 (5)	N1A—C1A—C2A	124.4 (5)
C11—C1—C2	119.8 (4)	C11A—C1A—C2A	121.1 (4)
C1—C2—H2A	109.5	C1A—C2A—H2A1	109.5
C1—C2—H2B	109.5	C1A—C2A—H2A2	109.5
H2A—C2—H2B	109.5	H2A1—C2A—H2A2	109.5
C1—C2—H2C	109.5	C1A—C2A—H2A3	109.5
H2A—C2—H2C	109.5	H2A1—C2A—H2A3	109.5
H2B—C2—H2C	109.5	H2A2—C2A—H2A3	109.5
N2—C3—N3	117.9 (4)	N3A—C3A—N2A	117.8 (4)
N2—C3—S1	120.7 (4)	N3A—C3A—S1A	122.2 (4)
N3—C3—S1	121.4 (4)	N2A—C3A—S1A	120.0 (4)
C12—C11—C16	117.7 (5)	C12A—C11A—C16A	118.4 (5)
C12—C11—C1	119.9 (5)	C12A—C11A—C1A	120.5 (4)
C16—C11—C1	122.4 (5)	C16A—C11A—C1A	121.1 (5)
C13—C12—C11	121.9 (5)	C13A—C12A—C11A	121.2 (5)
C13—C12—H12	119.1	C13A—C12A—H12A	119.4
C11—C12—H12	119.1	C11A—C12A—H12A	119.4
C12—C13—C14	118.8 (5)	C14A—C13A—C12A	119.5 (5)
C12—C13—H13	120.6	C14A—C13A—H13A	120.2
C14—C13—H13	120.6	C12A—C13A—H13A	120.2
O1—C14—C15	116.0 (5)	O1A—C14A—C13A	123.9 (5)
O1—C14—C13	123.6 (5)	O1A—C14A—C15A	115.6 (4)
C15—C14—C13	120.4 (5)	C13A—C14A—C15A	120.5 (5)
C16—C15—C14	120.3 (5)	C16A—C15A—C14A	119.4 (5)
C16—C15—H15	119.9	C16A—C15A—H15A	120.3
C14—C15—H15	119.9	C14A—C15A—H15A	120.3
C15—C16—C11	120.9 (5)	C15A—C16A—C11A	120.9 (5)
C15—C16—H16	119.6	C15A—C16A—H16A	119.5
C11—C16—H16	119.6	C11A—C16A—H16A	119.5
O1—C17—H17A	109.5	O1A—C17A—H17D	109.5
O1—C17—H17B	109.5	O1A—C17A—H17E	109.5
H17A—C17—H17B	109.5	H17D—C17A—H17E	109.5
O1—C17—H17C	109.5	O1A—C17A—H17F	109.5
H17A—C17—H17C	109.5	H17D—C17A—H17F	109.5
H17B—C17—H17C	109.5	H17E—C17A—H17F	109.5
C1—N1—N2—C3	161.5 (5)	C1A—N1A—N2A—C3A	167.8 (5)
N2—N1—C1—C11	173.8 (4)	N2A—N1A—C1A—C11A	177.5 (4)
N2—N1—C1—C2	−5.8 (8)	N2A—N1A—C1A—C2A	−4.4 (7)
N1—N2—C3—N3	−9.0 (7)	N1A—N2A—C3A—N3A	−7.4 (7)
N1—N2—C3—S1	172.2 (4)	N1A—N2A—C3A—S1A	174.4 (3)
N1—C1—C11—C12	−28.9 (7)	N1A—C1A—C11A—C12A	−23.1 (7)
C2—C1—C11—C12	150.7 (5)	C2A—C1A—C11A—C12A	158.7 (5)
N1—C1—C11—C16	151.7 (5)	N1A—C1A—C11A—C16A	153.8 (5)
C2—C1—C11—C16	−28.7 (8)	C2A—C1A—C11A—C16A	−24.3 (7)
C16—C11—C12—C13	0.1 (8)	C16A—C11A—C12A—C13A	−1.4 (8)
C1—C11—C12—C13	−179.3 (5)	C1A—C11A—C12A—C13A	175.6 (5)
C11—C12—C13—C14	−0.3 (8)	C11A—C12A—C13A—C14A	0.0 (8)
C17—O1—C14—C15	−176.3 (5)	C17A—O1A—C14A—C13A	2.9 (7)
C17—O1—C14—C13	4.6 (8)	C17A—O1A—C14A—C15A	−177.9 (5)
C12—C13—C14—O1	179.3 (5)	C12A—C13A—C14A—O1A	−180.0 (5)
C12—C13—C14—C15	0.2 (8)	C12A—C13A—C14A—C15A	0.9 (8)
O1—C14—C15—C16	−179.1 (5)	O1A—C14A—C15A—C16A	−179.7 (5)
C13—C14—C15—C16	0.1 (8)	C13A—C14A—C15A—C16A	−0.5 (8)
C14—C15—C16—C11	−0.3 (8)	C14A—C15A—C16A—C11A	−0.9 (8)
C12—C11—C16—C15	0.2 (8)	C12A—C11A—C16A—C15A	1.8 (8)
C1—C11—C16—C15	179.6 (5)	C1A—C11A—C16A—C15A	−175.2 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···S1^i	0.88	2.73	3.472 (4)	143
N3—H3A···O1A^ii	0.88	2.26	2.942 (5)	135
N3—H3B···S1^iii	0.88	2.54	3.355 (5)	154
N2A—H2N···S1A^iv	0.88	2.79	3.521 (4)	142
N3A—H3A1···O1^v	0.88	2.21	2.927 (6)	138
N3A—H3A2···S1A^vi	0.88	2.50	3.370 (5)	169

Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) −x+1, −y+1, −z+1; (iii) −x+1, y+1/2, −z+3/2; (iv) −x, y+1/2, −z+3/2; (v) −x+1, −y, −z+1; (vi) −x, y−1/2, −z+3/2.