1-(3-Chloro­phen­yl)-3-pivaloylthio­urea

Shoukat, N.; Rauf, M.K.; Bolte, M.; Badshah, A.

doi:10.1107/S1600536807028280

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1-(3-Chlorophenyl)-3-pivaloylthiourea

N. Shoukat, M. K. Rauf, M. Bolte and A. Badshah

The crystal structure of the title compound, C₁₂H₁₅ClN₂OS, is composed of discrete molecules with bond lengths and angles typical for thiourea compounds of this class. The molecule exists in the solid state in its thione form with typical thiourea C—S and C—O bond lengths, as well as shortened C—N bonds. The plane containing the thiourea group and the two attached C atoms is almost perpendicular to the benzene ring, forming a dihedral angle of 88.1 (3)°. An intramolecular N—H

O hydrogen bond stabilizes the packing arrangement and the molecules form intermolecular N—H

S hydrogen bonds to generate a chain. The tert-butyl group is disordered equally over two sites.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807028280/ez2082sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807028280/ez2082Isup2.hkl Contains datablock I

CCDC reference: 654951

checkCIF report

Key indicators

Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.002 Å
Disorder in main residue
R factor = 0.023
wR factor = 0.062
Data-to-parameter ratio = 19.6

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.77 Ratio
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.15 Ratio

Alert level C
PLAT213_ALERT_2_C Atom C32     has ADP max/min Ratio .............       3.30 prola
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C3
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.11
PLAT301_ALERT_3_C Main Residue  Disorder .........................      15.00 Perc.
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      19.10 Deg.
              C32  -C3   -C32'    1.555   1.555   1.555

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           29.60
           From the CIF: _reflns_number_total               3742
           Count of symmetry unique reflns         2173
           Completeness (_total/calc)            172.20%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1569
           Fraction of Friedel pairs measured     0.722
           Are heavy atom types Z>Si present        yes
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         30

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

The background to this study has been set out in our previous work on the structural chemistry of N,N'-disubstituted thioureas (Shoukat et al., 2007). Herein, as a continuation of these studies, the structure of the title compound (I) is described. A depiction of the molecule is given in Fig. 1. Bond lengths and angles, see the table of selected geometric parameters, can be regarded as typical for N,N'-disubstituted thiourea compounds as found in the Cambridge Structural Database v5.28 (Allen, 2002; Khawar Rauf et al., 2006). The molecule exists in the thione form with typical thiourea C—S and C—O bonds, as well as shortened C—N bond lengths. The thiocarbonyl and carbonyl groups are almost coplanar (see selected geometric parameters table). The molecule features an intramolecular N—H···O hydrogen bond and in the crystal structure, molecules associate via N—H···S intermolecular hydrogen bonds to form a chain (see the table of hydrogen bond geometries; Fig 2).

Related literature top

For related literature, see: Shoukat et al. (2007); Khawar Rauf et al. (2006); Allen (2002).

Experimental top

Freshly prepared pivaloylisothiocyanate (1.43 g, 10 mmol) was stirred in acetone (30 ml) for 15 minutes. Neat 3-chloroaniline (1.3 g, 10 mmol) was then added and the resulting mixture was stirred for 1 h. The reaction mixture was then poured into acidified (pH 4) water and stirred well. The solid product was separated and washed with deionized water and purified by recrystallization from methanol/ 1,1-dichloromethane (1:10 v/v) to give fine crystals of (I), with an overall yield of 85%.

Structure description top

For related literature, see: Shoukat et al. (2007); Khawar Rauf et al. (2006); Allen (2002).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; 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.

Figures top

	Fig. 1. Molecular structure of (I) showing atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Packing diagram of (I) with view onto the bc plane. Hydrogen bonds are shown as dashed lines.

1-(3-Chlorophenyl)-3-pivaloylthiourea top

Crystal data top

C₁₂H₁₅ClN₂OS	F(000) = 568
M_r = 270.77	D_x = 1.350 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 34614 reflections
a = 6.1269 (2) Å	θ = 3.5–29.8°
b = 10.2848 (4) Å	µ = 0.43 mm⁻¹
c = 21.1360 (9) Å	T = 173 K
V = 1331.86 (9) Å³	Block, colourless
Z = 4	0.49 × 0.49 × 0.47 mm

Data collection top

Stoe IPDSII two-circle diffractometer	3742 independent reflections
Radiation source: fine-focus sealed tube	3700 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.052
ω scans	θ_max = 29.6°, θ_min = 3.5°
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995)	h = −8→8
T_min = 0.817, T_max = 0.824	k = −14→14
35409 measured reflections	l = −29→29

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.023	w = 1/[σ²(F_o²) + (0.0361P)² + 0.1922P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.062	(Δ/σ)_max = 0.002
S = 1.04	Δρ_max = 0.22 e Å⁻³
3742 reflections	Δρ_min = −0.18 e Å⁻³
191 parameters	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
30 restraints	Extinction coefficient: 0.028 (2)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack, (1983), 1573 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: −0.01 (4)

Crystal data top

C₁₂H₁₅ClN₂OS	V = 1331.86 (9) Å³
M_r = 270.77	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 6.1269 (2) Å	µ = 0.43 mm⁻¹
b = 10.2848 (4) Å	T = 173 K
c = 21.1360 (9) Å	0.49 × 0.49 × 0.47 mm

Data collection top

Stoe IPDSII two-circle diffractometer	3742 independent reflections
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995)	3700 reflections with I > 2σ(I)
T_min = 0.817, T_max = 0.824	R_int = 0.052
35409 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.023	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.062	Δρ_max = 0.22 e Å⁻³
S = 1.04	Δρ_min = −0.18 e Å⁻³
3742 reflections	Absolute structure: Flack, (1983), 1573 Friedel pairs
191 parameters	Absolute structure parameter: −0.01 (4)
30 restraints

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Cl1	0.56583 (5)	0.11877 (3)	0.622329 (14)	0.03278 (8)
S1	0.71872 (4)	0.66862 (3)	0.541901 (12)	0.02455 (7)
O1	0.53343 (17)	0.53031 (9)	0.34538 (4)	0.0357 (2)
N1	0.51185 (16)	0.50045 (9)	0.46671 (4)	0.02377 (17)
H1	0.471 (3)	0.4776 (19)	0.4264 (9)	0.052 (5)*
N2	0.72061 (15)	0.65585 (8)	0.41596 (4)	0.02134 (16)
H2	0.821 (3)	0.7168 (17)	0.4228 (8)	0.040 (4)*
C1	0.64372 (15)	0.60313 (9)	0.47266 (5)	0.01990 (17)
C2	0.66320 (17)	0.61904 (11)	0.35498 (5)	0.02307 (19)
C3	0.76111 (18)	0.69697 (11)	0.30021 (5)	0.0255 (2)
C11	0.41745 (17)	0.43202 (9)	0.51909 (5)	0.02176 (18)
C12	0.52851 (16)	0.32519 (10)	0.54368 (5)	0.02213 (18)
H12	0.6688	0.3019	0.5283	0.027*
C13	0.42847 (18)	0.25339 (10)	0.59147 (5)	0.02302 (19)
C14	0.2224 (2)	0.28558 (11)	0.61466 (5)	0.0260 (2)
H14	0.1563	0.2352	0.6471	0.031*
C15	0.11545 (18)	0.39324 (12)	0.58923 (5)	0.0283 (2)
H15	−0.0247	0.4166	0.6047	0.034*
C16	0.21162 (18)	0.46708 (10)	0.54130 (5)	0.02590 (19)
H16	0.1377	0.5402	0.5241	0.031*
C31	0.6919 (19)	0.8377 (6)	0.3090 (4)	0.075 (3)	0.501 (14)
H31A	0.7498	0.8706	0.3492	0.112*	0.501 (14)
H31B	0.5322	0.8431	0.3095	0.112*	0.501 (14)
H31C	0.7491	0.8903	0.2741	0.112*	0.501 (14)
C32	0.6826 (14)	0.6375 (10)	0.2402 (3)	0.072 (3)	0.501 (14)
H32A	0.7430	0.6855	0.2041	0.108*	0.501 (14)
H32B	0.5229	0.6411	0.2387	0.108*	0.501 (14)
H32C	0.7303	0.5466	0.2381	0.108*	0.501 (14)
C33	1.0128 (9)	0.6913 (7)	0.3023 (3)	0.0448 (12)	0.501 (14)
H33A	1.0646	0.7296	0.3420	0.067*	0.501 (14)
H33B	1.0729	0.7401	0.2665	0.067*	0.501 (14)
H33C	1.0606	0.6005	0.2998	0.067*	0.501 (14)
C31'	0.6110 (11)	0.8150 (7)	0.2875 (3)	0.0556 (14)	0.499 (14)
H31D	0.4607	0.7849	0.2814	0.083*	0.499 (14)
H31E	0.6605	0.8604	0.2493	0.083*	0.499 (14)
H31F	0.6168	0.8746	0.3236	0.083*	0.499 (14)
C32'	0.7525 (16)	0.6115 (6)	0.2407 (3)	0.058 (2)	0.499 (14)
H32D	0.6026	0.5814	0.2338	0.087*	0.499 (14)
H32E	0.8488	0.5363	0.2462	0.087*	0.499 (14)
H32F	0.8007	0.6622	0.2040	0.087*	0.499 (14)
C33'	0.9919 (10)	0.7433 (11)	0.3097 (3)	0.0562 (19)	0.499 (14)
H33D	1.0396	0.7918	0.2722	0.084*	0.499 (14)
H33E	1.0880	0.6682	0.3161	0.084*	0.499 (14)
H33F	0.9985	0.7999	0.3469	0.084*	0.499 (14)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.04062 (15)	0.02760 (12)	0.03014 (13)	0.00457 (11)	−0.00164 (11)	0.00577 (10)
S1	0.02621 (11)	0.02688 (12)	0.02055 (11)	−0.00204 (9)	−0.00021 (9)	−0.00280 (9)
O1	0.0454 (5)	0.0378 (5)	0.0238 (4)	−0.0202 (4)	−0.0028 (4)	0.0016 (3)
N1	0.0308 (4)	0.0221 (4)	0.0184 (4)	−0.0057 (3)	0.0028 (3)	−0.0004 (3)
N2	0.0240 (4)	0.0209 (3)	0.0191 (4)	−0.0036 (3)	0.0014 (3)	0.0001 (3)
C1	0.0200 (4)	0.0185 (4)	0.0212 (4)	0.0025 (3)	0.0025 (3)	0.0009 (3)
C2	0.0266 (4)	0.0229 (4)	0.0197 (4)	−0.0017 (4)	0.0002 (3)	0.0014 (4)
C3	0.0312 (5)	0.0255 (4)	0.0198 (4)	−0.0044 (4)	0.0005 (4)	0.0033 (4)
C11	0.0247 (4)	0.0215 (4)	0.0190 (4)	−0.0034 (4)	0.0031 (4)	−0.0006 (3)
C12	0.0220 (4)	0.0238 (4)	0.0207 (4)	−0.0019 (3)	0.0014 (3)	−0.0013 (4)
C13	0.0274 (5)	0.0214 (4)	0.0203 (4)	−0.0014 (4)	−0.0018 (4)	0.0002 (3)
C14	0.0296 (5)	0.0278 (5)	0.0205 (4)	−0.0051 (4)	0.0051 (4)	0.0003 (4)
C15	0.0261 (5)	0.0324 (5)	0.0264 (5)	0.0012 (4)	0.0074 (4)	−0.0012 (4)
C16	0.0276 (4)	0.0254 (4)	0.0247 (5)	0.0029 (4)	0.0025 (4)	0.0006 (4)
C31	0.118 (6)	0.039 (2)	0.068 (4)	0.031 (3)	0.045 (4)	0.032 (2)
C32	0.077 (4)	0.120 (6)	0.019 (2)	−0.063 (4)	−0.013 (2)	0.018 (3)
C33	0.0357 (15)	0.060 (3)	0.0384 (19)	−0.0093 (19)	0.0065 (13)	0.016 (2)
C31'	0.067 (3)	0.052 (3)	0.048 (3)	0.025 (2)	0.018 (2)	0.027 (2)
C32'	0.106 (6)	0.0388 (18)	0.029 (2)	−0.036 (3)	0.022 (3)	−0.0107 (15)
C33'	0.043 (2)	0.092 (5)	0.034 (2)	−0.034 (3)	−0.0109 (18)	0.030 (3)

Geometric parameters (Å, º) top

Cl1—C13	1.7466 (11)	C14—H14	0.9500
S1—C1	1.6753 (10)	C15—C16	1.3965 (15)
O1—C2	1.2272 (13)	C15—H15	0.9500
N1—C1	1.3356 (13)	C16—H16	0.9500
N1—C11	1.4337 (13)	C31—H31A	0.9800
N1—H1	0.918 (19)	C31—H31B	0.9800
N2—C2	1.3887 (13)	C31—H31C	0.9800
N2—C1	1.3972 (12)	C32—H32A	0.9800
N2—H2	0.889 (18)	C32—H32B	0.9800
C2—C3	1.5304 (14)	C32—H32C	0.9800
C3—C32	1.489 (6)	C33—H33A	0.9800
C3—C33'	1.506 (5)	C33—H33B	0.9800
C3—C31	1.520 (5)	C33—H33C	0.9800
C3—C32'	1.536 (5)	C31'—H31D	0.9800
C3—C33	1.544 (5)	C31'—H31E	0.9800
C3—C31'	1.547 (5)	C31'—H31F	0.9800
C11—C16	1.3931 (14)	C32'—H32D	0.9800
C11—C12	1.3930 (14)	C32'—H32E	0.9800
C12—C13	1.3932 (14)	C32'—H32F	0.9800
C12—H12	0.9500	C33'—H33D	0.9800
C13—C14	1.3940 (16)	C33'—H33E	0.9800
C14—C15	1.3945 (16)	C33'—H33F	0.9800

C1—N1—C11	124.02 (9)	C11—C16—C15	119.05 (10)
C1—N1—H1	117.0 (12)	C11—C16—H16	120.5
C11—N1—H1	118.8 (13)	C15—C16—H16	120.5
C2—N2—C1	127.23 (9)	C3—C31—H31A	109.5
C2—N2—H2	121.2 (11)	C3—C31—H31B	109.5
C1—N2—H2	111.5 (11)	H31A—C31—H31B	109.5
N1—C1—N2	115.47 (9)	C3—C31—H31C	109.5
N1—C1—S1	124.48 (8)	H31A—C31—H31C	109.5
N2—C1—S1	120.05 (7)	H31B—C31—H31C	109.5
O1—C2—N2	121.35 (9)	C3—C32—H32A	109.5
O1—C2—C3	121.22 (9)	C3—C32—H32B	109.5
N2—C2—C3	117.39 (9)	H32A—C32—H32B	109.5
C32—C3—C31	114.0 (4)	C3—C32—H32C	109.5
C32—C3—C2	107.6 (3)	H32A—C32—H32C	109.5
C33'—C3—C2	115.7 (2)	H32B—C32—H32C	109.5
C31—C3—C2	107.3 (2)	C3—C33—H33A	109.5
C32—C3—C32'	19.1 (5)	C3—C33—H33B	109.5
C33'—C3—C32'	108.8 (4)	H33A—C33—H33B	109.5
C2—C3—C32'	107.8 (3)	C3—C33—H33C	109.5
C32—C3—C33	109.4 (4)	H33A—C33—H33C	109.5
C31—C3—C33	108.1 (4)	H33B—C33—H33C	109.5
C2—C3—C33	110.5 (3)	C3—C31'—H31D	109.5
C33'—C3—C31'	109.5 (4)	C3—C31'—H31E	109.5
C2—C3—C31'	108.0 (2)	H31D—C31'—H31E	109.5
C32'—C3—C31'	106.6 (3)	C3—C31'—H31F	109.5
C16—C11—C12	121.37 (9)	H31D—C31'—H31F	109.5
C16—C11—N1	119.89 (9)	H31E—C31'—H31F	109.5
C12—C11—N1	118.57 (9)	C3—C32'—H32D	109.5
C11—C12—C13	118.27 (9)	C3—C32'—H32E	109.5
C11—C12—H12	120.9	H32D—C32'—H32E	109.5
C13—C12—H12	120.9	C3—C32'—H32F	109.5
C12—C13—C14	121.83 (10)	H32D—C32'—H32F	109.5
C12—C13—Cl1	118.61 (8)	H32E—C32'—H32F	109.5
C14—C13—Cl1	119.56 (8)	C3—C33'—H33D	109.5
C13—C14—C15	118.60 (10)	C3—C33'—H33E	109.5
C13—C14—H14	120.7	H33D—C33'—H33E	109.5
C15—C14—H14	120.7	C3—C33'—H33F	109.5
C14—C15—C16	120.87 (10)	H33D—C33'—H33F	109.5
C14—C15—H15	119.6	H33E—C33'—H33F	109.5
C16—C15—H15	119.6

C11—N1—C1—N2	179.50 (9)	N2—C2—C3—C33	58.8 (3)
C11—N1—C1—S1	−0.31 (15)	O1—C2—C3—C31'	90.7 (4)
C2—N2—C1—N1	4.83 (15)	N2—C2—C3—C31'	−87.0 (4)
C2—N2—C1—S1	−175.35 (8)	C1—N1—C11—C16	92.59 (13)
C1—N2—C2—O1	−0.89 (17)	C1—N1—C11—C12	−92.01 (13)
C1—N2—C2—C3	176.75 (9)	C16—C11—C12—C13	−0.02 (15)
O1—C2—C3—C32	−4.2 (5)	N1—C11—C12—C13	−175.36 (9)
N2—C2—C3—C32	178.2 (5)	C11—C12—C13—C14	0.19 (15)
O1—C2—C3—C33'	−146.3 (5)	C11—C12—C13—Cl1	179.68 (7)
N2—C2—C3—C33'	36.1 (5)	C12—C13—C14—C15	−0.34 (16)
O1—C2—C3—C31	118.8 (6)	Cl1—C13—C14—C15	−179.83 (9)
N2—C2—C3—C31	−58.8 (6)	C13—C14—C15—C16	0.33 (17)
O1—C2—C3—C32'	−24.3 (4)	C12—C11—C16—C15	0.02 (16)
N2—C2—C3—C32'	158.1 (4)	N1—C11—C16—C15	175.29 (10)
O1—C2—C3—C33	−123.5 (3)	C14—C15—C16—C11	−0.18 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.918 (19)	1.836 (19)	2.5863 (12)	137.2 (18)
N2—H2···S1ⁱ	0.889 (18)	2.808 (18)	3.6560 (9)	159.8 (14)

Symmetry code: (i) x+1/2, −y+3/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₅ClN₂OS
M_r	270.77
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	173
a, b, c (Å)	6.1269 (2), 10.2848 (4), 21.1360 (9)
V (Å³)	1331.86 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.43
Crystal size (mm)	0.49 × 0.49 × 0.47

Data collection
Diffractometer	Stoe IPDSII two-circle
Absorption correction	Multi-scan (MULABS; Spek, 2003; Blessing, 1995)
T_min, T_max	0.817, 0.824
No. of measured, independent and observed [I > 2σ(I)] reflections	35409, 3742, 3700
R_int	0.052
(sin θ/λ)_max (Å⁻¹)	0.695

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.023, 0.062, 1.04
No. of reflections	3742
No. of parameters	191
No. of restraints	30
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.18
Absolute structure	Flack, (1983), 1573 Friedel pairs
Absolute structure parameter	−0.01 (4)

Computer programs: X-AREA (Stoe & Cie, 2001), X-AREA, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), XP in SHELXTL-Plus (Sheldrick, 1991), SHELXL97.

Selected geometric parameters (Å, º) top

S1—C1	1.6753 (10)	N1—C11	1.4337 (13)
O1—C2	1.2272 (13)	N2—C2	1.3887 (13)
N1—C1	1.3356 (13)	N2—C1	1.3972 (12)

C2—N2—C1—N1	4.83 (15)	C1—N2—C2—O1	−0.89 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.918 (19)	1.836 (19)	2.5863 (12)	137.2 (18)
N2—H2···S1ⁱ	0.889 (18)	2.808 (18)	3.6560 (9)	159.8 (14)

Symmetry code: (i) x+1/2, −y+3/2, −z+1.

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