Crystal structure of 1-benzoyl-3-(4-fluoro-phen-yl)thio-urea.

The title compound, C14H11FN2OS, contains two mol-ecules (A and B) in the asymmetric unit, with different conformations. In mol-ecule A, the dihedral angles between the central thio-urea grouping and the phenyl and fluoro-benzene rings are 28.77 (8) and 41.82 (8)°, respectively, and the dihedral angle between the ring planes is 70.02 (9)°. Equivalent data for mol-ecule B are 8.46 (8), 47.78 (8) and 52.99 (9)°, respectively. Both mol-ecules feature an intra-molecular N-H⋯O hydrogen bond, which closes an S(6) ring. In the crystal, A+B dimers linked by pairs of N-H⋯S hydrogen bonds generate R 2 (2)(8) loops.

Related literature

For related structures, see: Othman et al. (2010 ▶); Rauf et al. (2012 ▶) Saeed & Flörke (2006a ▶, 2006b ▶); Saeed et al. (2011 ▶); Yamin & Yusof (2003a ▶,b ▶).

Experimental

Crystal data

C14H11FN2OS

M = 274.31

Triclinic,

a = 9.6265 (4) Å

b = 11.1329 (4) Å

c = 13.8252 (5) Å

α = 110.646 (3)°

β = 100.708 (3)°

γ = 102.762 (3)°

V = 1294.58 (9) Å3

Z = 4

Cu Kα radiation

μ = 2.28 mm−1

T = 296 K

0.36 × 0.28 × 0.22 mm

Data collection

Agilent SuperNova, Dual, Cu at zero, Atlas, CCD diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T min = 0.817, T max = 1.000

11636 measured reflections

5354 independent reflections

4757 reflections with I > 2σ(I)

R int = 0.015

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.102

S = 1.03

5354 reflections

346 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.35 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: WinGX (Farrugia, 2012 ▶) and X-SEED (Barbour, 2001 ▶).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536814018376/hb7271sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814018376/hb7271Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814018376/hb7271Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S1600536814018376/hb7271fig1.tif

The mol­ecular structure of (I) with 50% displacement ellipsoids.

Click here for additional data file.

. DOI: 10.1107/S1600536814018376/hb7271fig2.tif

The inter and intra­molecular hydrogen bonding shown using dashed lines.

CCDC reference: 1018979

Additional supporting information: crystallographic information; 3D view; checkCIF report

C14H11FN2OS	V = 1294.58 (9) Å3
Mr = 274.31	Z = 4
Triclinic, P1	F(000) = 568
Hall symbol: -P 1	Dx = 1.407 Mg m−3
a = 9.6265 (4) Å	Cu Kα radiation, λ = 1.54184 Å
b = 11.1329 (4) Å	µ = 2.28 mm−1
c = 13.8252 (5) Å	T = 296 K
α = 110.646 (3)°	Block, colorless
β = 100.708 (3)°	0.36 × 0.28 × 0.22 mm
γ = 102.762 (3)°

Agilent SuperNova, Dual, Cu at zero, Atlas, CCD diffractometer	5354 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	4757 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.015
ω scans	θmax = 76.5°, θmin = 4.4°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	h = −12→11
Tmin = 0.817, Tmax = 1.000	k = −13→12
11636 measured reflections	l = −11→17

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0538P)2 + 0.268P] where P = (Fo2 + 2Fc2)/3
5354 reflections	(Δ/σ)max = 0.001
346 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.35 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
S1	0.10971 (5)	0.71506 (4)	0.58605 (3)	0.05533 (12)
S2	0.99550 (5)	1.23786 (4)	0.68544 (4)	0.06368 (14)
F1	0.42593 (15)	0.61882 (14)	1.00154 (8)	0.0807 (3)
F2	1.30145 (16)	1.00061 (14)	1.00287 (10)	0.0960 (4)
O1	0.30327 (17)	0.41067 (15)	0.38650 (9)	0.0768 (4)
O2	0.67259 (14)	0.81808 (11)	0.48289 (10)	0.0626 (3)
N1	0.28430 (16)	0.55698 (14)	0.57813 (10)	0.0533 (3)
N2	0.17580 (15)	0.56414 (13)	0.41761 (9)	0.0483 (3)
N3	0.91440 (14)	0.97471 (12)	0.64274 (10)	0.0513 (3)
N4	0.78454 (14)	1.03902 (13)	0.52148 (10)	0.0504 (3)
C1	0.19583 (17)	0.60743 (14)	0.52881 (11)	0.0454 (3)
C2	0.31803 (16)	0.57760 (15)	0.68871 (11)	0.0456 (3)
C3	0.3556 (2)	0.70415 (16)	0.77249 (13)	0.0559 (4)
H3A	0.3568	0.7797	0.7578	0.067*
C4	0.39115 (19)	0.71680 (17)	0.87823 (12)	0.0586 (4)
H4A	0.4153	0.8006	0.9354	0.070*
C5	0.39026 (18)	0.60464 (18)	0.89724 (12)	0.0543 (4)
C6	0.3546 (2)	0.47939 (18)	0.81661 (14)	0.0583 (4)
H6	0.3548	0.4046	0.8321	0.070*
C7	0.31813 (18)	0.46637 (16)	0.71082 (12)	0.0526 (3)
H7	0.2935	0.3819	0.6544	0.063*
C8	0.22178 (18)	0.46495 (16)	0.35187 (12)	0.0505 (3)
C9	0.16680 (16)	0.42877 (14)	0.23398 (11)	0.0438 (3)
C10	0.02856 (17)	0.43219 (15)	0.18570 (12)	0.0475 (3)
H10	−0.0331	0.4603	0.2274	0.057*
C11	−0.01708 (19)	0.39336 (17)	0.07491 (13)	0.0549 (4)
H11	−0.1100	0.3949	0.0423	0.066*
C12	0.0745 (2)	0.35248 (17)	0.01270 (12)	0.0571 (4)
H12	0.0438	0.3275	−0.0614	0.069*
C13	0.2114 (2)	0.34884 (18)	0.06075 (13)	0.0585 (4)
H13	0.2733	0.3216	0.0189	0.070*
C14	0.25746 (18)	0.38540 (16)	0.17091 (12)	0.0524 (3)
H14	0.3491	0.3809	0.2027	0.063*
C15	0.89789 (16)	1.07566 (15)	0.61595 (12)	0.0466 (3)
C16	1.01650 (17)	0.98710 (14)	0.73730 (12)	0.0470 (3)
C17	1.16625 (18)	1.05699 (17)	0.76648 (13)	0.0541 (4)
H17	1.2019	1.1011	0.7259	0.065*
C18	1.2625 (2)	1.06121 (19)	0.85570 (15)	0.0637 (4)
H18	1.3633	1.1082	0.8761	0.076*
C19	1.2071 (2)	0.99480 (18)	0.91389 (14)	0.0635 (4)
C20	1.0604 (2)	0.92345 (18)	0.88583 (16)	0.0668 (5)
H20	1.0258	0.8785	0.9262	0.080*
C21	0.9641 (2)	0.91938 (16)	0.79610 (15)	0.0584 (4)
H21	0.8638	0.8708	0.7754	0.070*
C22	0.67355 (17)	0.91742 (15)	0.46324 (12)	0.0482 (3)
C23	0.55378 (16)	0.91245 (15)	0.37529 (12)	0.0475 (3)
C24	0.53131 (18)	1.02572 (19)	0.36376 (15)	0.0609 (4)
H24	0.5928	1.1114	0.4126	0.073*
C25	0.4163 (2)	1.0108 (2)	0.27875 (18)	0.0735 (5)
H25	0.4017	1.0869	0.2705	0.088*
C26	0.3241 (2)	0.8846 (2)	0.20673 (16)	0.0721 (5)
H26	0.2483	0.8755	0.1495	0.086*
C27	0.3438 (2)	0.7719 (2)	0.21907 (15)	0.0713 (5)
H27	0.2803	0.6866	0.1709	0.086*
C28	0.45776 (19)	0.78475 (18)	0.30293 (14)	0.0610 (4)
H28	0.4705	0.7082	0.3112	0.073*
H2	0.1172	0.6095	0.3842	0.073*
H4	0.7819	1.1067	0.4974	0.073*
H3	0.8390	0.8878	0.5964	0.073*
H1	0.316 (2)	0.497 (2)	0.5386 (17)	0.073*

	U11	U22	U33	U12	U13	U23
S1	0.0705 (3)	0.0524 (2)	0.0459 (2)	0.02927 (18)	0.02121 (17)	0.01513 (16)
S2	0.0710 (3)	0.0427 (2)	0.0561 (2)	0.00407 (18)	−0.00598 (19)	0.01671 (17)
F1	0.0990 (8)	0.1050 (9)	0.0398 (5)	0.0368 (7)	0.0174 (5)	0.0300 (5)
F2	0.1099 (10)	0.0882 (9)	0.0716 (7)	0.0323 (7)	−0.0158 (7)	0.0321 (7)
O1	0.1027 (10)	0.0990 (10)	0.0416 (6)	0.0699 (9)	0.0178 (6)	0.0220 (6)
O2	0.0697 (7)	0.0427 (6)	0.0563 (7)	0.0099 (5)	−0.0017 (5)	0.0133 (5)
N1	0.0669 (8)	0.0583 (8)	0.0355 (6)	0.0310 (7)	0.0137 (6)	0.0137 (5)
N2	0.0616 (7)	0.0484 (7)	0.0353 (6)	0.0238 (6)	0.0130 (5)	0.0140 (5)
N3	0.0537 (7)	0.0411 (6)	0.0465 (7)	0.0127 (5)	0.0024 (5)	0.0112 (5)
N4	0.0534 (7)	0.0444 (6)	0.0437 (6)	0.0091 (5)	0.0043 (5)	0.0158 (5)
C1	0.0529 (8)	0.0406 (7)	0.0372 (7)	0.0126 (6)	0.0117 (6)	0.0118 (5)
C2	0.0477 (7)	0.0486 (8)	0.0357 (7)	0.0153 (6)	0.0101 (6)	0.0125 (6)
C3	0.0672 (10)	0.0456 (8)	0.0446 (8)	0.0137 (7)	0.0086 (7)	0.0131 (6)
C4	0.0646 (10)	0.0559 (9)	0.0372 (7)	0.0166 (7)	0.0060 (7)	0.0045 (6)
C5	0.0535 (8)	0.0705 (10)	0.0363 (7)	0.0190 (7)	0.0121 (6)	0.0194 (7)
C6	0.0665 (10)	0.0565 (9)	0.0523 (9)	0.0174 (8)	0.0129 (7)	0.0260 (7)
C7	0.0610 (9)	0.0454 (8)	0.0419 (7)	0.0172 (7)	0.0091 (6)	0.0098 (6)
C8	0.0583 (9)	0.0552 (8)	0.0385 (7)	0.0255 (7)	0.0136 (6)	0.0152 (6)
C9	0.0513 (7)	0.0404 (7)	0.0373 (7)	0.0153 (6)	0.0124 (6)	0.0130 (5)
C10	0.0515 (8)	0.0466 (7)	0.0440 (7)	0.0179 (6)	0.0142 (6)	0.0163 (6)
C11	0.0580 (9)	0.0562 (9)	0.0472 (8)	0.0172 (7)	0.0067 (7)	0.0220 (7)
C12	0.0724 (10)	0.0552 (9)	0.0378 (7)	0.0145 (8)	0.0122 (7)	0.0174 (7)
C13	0.0662 (10)	0.0641 (10)	0.0443 (8)	0.0213 (8)	0.0246 (7)	0.0162 (7)
C14	0.0520 (8)	0.0582 (9)	0.0449 (8)	0.0206 (7)	0.0148 (6)	0.0164 (7)
C15	0.0488 (7)	0.0439 (7)	0.0411 (7)	0.0128 (6)	0.0100 (6)	0.0130 (6)
C16	0.0516 (8)	0.0388 (7)	0.0444 (7)	0.0181 (6)	0.0095 (6)	0.0100 (6)
C17	0.0512 (8)	0.0591 (9)	0.0493 (8)	0.0194 (7)	0.0151 (7)	0.0177 (7)
C18	0.0534 (9)	0.0623 (10)	0.0594 (10)	0.0188 (8)	0.0046 (7)	0.0125 (8)
C19	0.0767 (11)	0.0530 (9)	0.0506 (9)	0.0284 (8)	−0.0005 (8)	0.0143 (7)
C20	0.0863 (13)	0.0541 (9)	0.0666 (11)	0.0264 (9)	0.0169 (9)	0.0322 (8)
C21	0.0587 (9)	0.0454 (8)	0.0697 (10)	0.0152 (7)	0.0107 (8)	0.0268 (7)
C22	0.0510 (8)	0.0445 (7)	0.0404 (7)	0.0131 (6)	0.0115 (6)	0.0096 (6)
C23	0.0444 (7)	0.0531 (8)	0.0406 (7)	0.0131 (6)	0.0142 (6)	0.0143 (6)
C24	0.0480 (8)	0.0605 (10)	0.0698 (11)	0.0093 (7)	0.0105 (7)	0.0298 (8)
C25	0.0551 (10)	0.0889 (14)	0.0904 (14)	0.0205 (9)	0.0156 (9)	0.0564 (12)
C26	0.0524 (9)	0.1022 (15)	0.0569 (10)	0.0162 (10)	0.0074 (8)	0.0364 (10)
C27	0.0607 (10)	0.0747 (12)	0.0524 (10)	0.0125 (9)	0.0015 (8)	0.0093 (9)
C28	0.0578 (9)	0.0569 (9)	0.0507 (9)	0.0143 (7)	0.0055 (7)	0.0093 (7)

S1—C1	1.6623 (15)	C10—C11	1.388 (2)
S2—C15	1.6608 (15)	C10—H10	0.9300
F1—C5	1.3616 (17)	C11—C12	1.381 (2)
F2—C19	1.3585 (19)	C11—H11	0.9300
O1—C8	1.2181 (19)	C12—C13	1.377 (2)
O2—C22	1.2269 (19)	C12—H12	0.9300
N1—C1	1.3309 (19)	C13—C14	1.383 (2)
N1—C2	1.4250 (18)	C13—H13	0.9300
N1—H1	0.86 (2)	C14—H14	0.9300
N2—C8	1.3781 (19)	C16—C21	1.379 (2)
N2—C1	1.3998 (18)	C16—C17	1.383 (2)
N2—H2	0.9905	C17—C18	1.378 (2)
N3—C15	1.3327 (19)	C17—H17	0.9300
N3—C16	1.4246 (19)	C18—C19	1.372 (3)
N3—H3	0.9761	C18—H18	0.9300
N4—C22	1.3767 (19)	C19—C20	1.364 (3)
N4—C15	1.4004 (19)	C20—C21	1.384 (2)
N4—H4	0.9287	C20—H20	0.9300
C2—C7	1.376 (2)	C21—H21	0.9300
C2—C3	1.388 (2)	C22—C23	1.488 (2)
C3—C4	1.386 (2)	C23—C24	1.383 (2)
C3—H3A	0.9300	C23—C28	1.396 (2)
C4—C5	1.362 (2)	C24—C25	1.390 (3)
C4—H4A	0.9300	C24—H24	0.9300
C5—C6	1.362 (2)	C25—C26	1.374 (3)
C6—C7	1.386 (2)	C25—H25	0.9300
C6—H6	0.9300	C26—C27	1.372 (3)
C7—H7	0.9300	C26—H26	0.9300
C8—C9	1.4904 (19)	C27—C28	1.382 (2)
C9—C14	1.388 (2)	C27—H27	0.9300
C9—C10	1.389 (2)	C28—H28	0.9300
C1—N1—C2	127.39 (13)	C12—C13—C14	120.38 (15)
C1—N1—H1	117.5 (14)	C12—C13—H13	119.8
C2—N1—H1	114.6 (14)	C14—C13—H13	119.8
C8—N2—C1	127.90 (12)	C13—C14—C9	119.97 (15)
C8—N2—H2	118.4	C13—C14—H14	120.0
C1—N2—H2	113.6	C9—C14—H14	120.0
C15—N3—C16	126.08 (12)	N3—C15—N4	115.58 (13)
C15—N3—H3	114.0	N3—C15—S2	126.05 (11)
C16—N3—H3	119.4	N4—C15—S2	118.34 (11)
C22—N4—C15	127.94 (13)	C21—C16—C17	120.04 (15)
C22—N4—H4	116.5	C21—C16—N3	118.07 (14)
C15—N4—H4	115.5	C17—C16—N3	121.74 (14)
N1—C1—N2	115.29 (13)	C18—C17—C16	119.95 (16)
N1—C1—S1	126.60 (11)	C18—C17—H17	120.0
N2—C1—S1	118.10 (11)	C16—C17—H17	120.0
C7—C2—C3	120.12 (14)	C19—C18—C17	118.83 (17)
C7—C2—N1	117.19 (13)	C19—C18—H18	120.6
C3—C2—N1	122.63 (14)	C17—C18—H18	120.6
C4—C3—C2	119.32 (15)	F2—C19—C20	118.72 (18)
C4—C3—H3A	120.3	F2—C19—C18	118.92 (18)
C2—C3—H3A	120.3	C20—C19—C18	122.36 (16)
C5—C4—C3	119.02 (15)	C19—C20—C21	118.61 (17)
C5—C4—H4A	120.5	C19—C20—H20	120.7
C3—C4—H4A	120.5	C21—C20—H20	120.7
F1—C5—C6	118.81 (16)	C16—C21—C20	120.20 (17)
F1—C5—C4	118.31 (15)	C16—C21—H21	119.9
C6—C5—C4	122.88 (15)	C20—C21—H21	119.9
C5—C6—C7	118.19 (15)	O2—C22—N4	121.91 (14)
C5—C6—H6	120.9	O2—C22—C23	121.47 (14)
C7—C6—H6	120.9	N4—C22—C23	116.62 (13)
C2—C7—C6	120.45 (14)	C24—C23—C28	119.36 (15)
C2—C7—H7	119.8	C24—C23—C22	123.87 (14)
C6—C7—H7	119.8	C28—C23—C22	116.76 (14)
O1—C8—N2	123.06 (13)	C23—C24—C25	119.67 (17)
O1—C8—C9	121.47 (13)	C23—C24—H24	120.2
N2—C8—C9	115.47 (13)	C25—C24—H24	120.2
C14—C9—C10	119.75 (13)	C26—C25—C24	120.52 (19)
C14—C9—C8	117.40 (13)	C26—C25—H25	119.7
C10—C9—C8	122.81 (13)	C24—C25—H25	119.7
C11—C10—C9	119.64 (14)	C27—C26—C25	120.09 (18)
C11—C10—H10	120.2	C27—C26—H26	120.0
C9—C10—H10	120.2	C25—C26—H26	120.0
C12—C11—C10	120.43 (15)	C26—C27—C28	120.17 (18)
C12—C11—H11	119.8	C26—C27—H27	119.9
C10—C11—H11	119.8	C28—C27—H27	119.9
C13—C12—C11	119.81 (14)	C27—C28—C23	120.16 (18)
C13—C12—H12	120.1	C27—C28—H28	119.9
C11—C12—H12	120.1	C23—C28—H28	119.9
C2—N1—C1—N2	−176.44 (14)	C16—N3—C15—N4	−176.80 (14)
C2—N1—C1—S1	3.8 (2)	C16—N3—C15—S2	1.6 (2)
C8—N2—C1—N1	8.3 (2)	C22—N4—C15—N3	11.7 (2)
C8—N2—C1—S1	−171.98 (13)	C22—N4—C15—S2	−166.79 (13)
C1—N1—C2—C7	136.52 (17)	C15—N3—C16—C21	132.89 (17)
C1—N1—C2—C3	−46.1 (2)	C15—N3—C16—C17	−51.5 (2)
C7—C2—C3—C4	−0.8 (3)	C21—C16—C17—C18	−1.3 (2)
N1—C2—C3—C4	−178.15 (15)	N3—C16—C17—C18	−176.91 (14)
C2—C3—C4—C5	0.9 (3)	C16—C17—C18—C19	0.3 (3)
C3—C4—C5—F1	179.79 (15)	C17—C18—C19—F2	−178.97 (16)
C3—C4—C5—C6	−0.5 (3)	C17—C18—C19—C20	0.8 (3)
F1—C5—C6—C7	179.82 (15)	F2—C19—C20—C21	179.03 (16)
C4—C5—C6—C7	0.2 (3)	C18—C19—C20—C21	−0.7 (3)
C3—C2—C7—C6	0.4 (2)	C17—C16—C21—C20	1.4 (2)
N1—C2—C7—C6	177.91 (15)	N3—C16—C21—C20	177.13 (15)
C5—C6—C7—C2	−0.1 (3)	C19—C20—C21—C16	−0.4 (3)
C1—N2—C8—O1	−8.6 (3)	C15—N4—C22—O2	−8.8 (3)
C1—N2—C8—C9	172.24 (14)	C15—N4—C22—C23	170.92 (14)
O1—C8—C9—C14	−29.9 (2)	O2—C22—C23—C24	165.86 (16)
N2—C8—C9—C14	149.29 (15)	N4—C22—C23—C24	−13.8 (2)
O1—C8—C9—C10	147.74 (18)	O2—C22—C23—C28	−12.5 (2)
N2—C8—C9—C10	−33.1 (2)	N4—C22—C23—C28	167.86 (14)
C14—C9—C10—C11	−0.6 (2)	C28—C23—C24—C25	−1.8 (3)
C8—C9—C10—C11	−178.13 (14)	C22—C23—C24—C25	179.94 (16)
C9—C10—C11—C12	−0.5 (2)	C23—C24—C25—C26	0.6 (3)
C10—C11—C12—C13	0.7 (3)	C24—C25—C26—C27	0.8 (3)
C11—C12—C13—C14	0.3 (3)	C25—C26—C27—C28	−1.0 (3)
C12—C13—C14—C9	−1.4 (3)	C26—C27—C28—C23	−0.3 (3)
C10—C9—C14—C13	1.5 (2)	C24—C23—C28—C27	1.6 (3)
C8—C9—C14—C13	179.19 (15)	C22—C23—C28—C27	−179.96 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···S2i	0.99	2.56	3.5433 (13)	170
N4—H4···S1i	0.93	2.74	3.5976 (13)	154
N1—H1···O1	0.86 (2)	1.95 (2)	2.6408 (17)	137.5 (19)
N3—H3···O2	0.98	1.81	2.6307 (17)	139

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯S2i	0.99	2.56	3.5433 (13)	170
N4—H4⋯S1i	0.93	2.74	3.5976 (13)	154
N1—H1⋯O1	0.86 (2)	1.95 (2)	2.6408 (17)	137.5 (19)
N3—H3⋯O2	0.98	1.81	2.6307 (17)	139

Symmetry code: (i) .