Bromidobis(N,N'-diphenyl-thio-urea-κS)copper(I) monohydrate.

In the title compound, [CuBr(C(13)H(12)N(2)S)(2)]·H(2)O, the Cu(I) atom adopts a slightly distorted trigonal-planar coordination arising from two S atoms of two diphenyl-thio-urea ligands and a bromide ion. There are two intra-molecular N-H⋯Br hydrogen bonds completing twisted six-membered rings with R(6) motifs. The dihedral angles between the aromatic rings in the ligands are 62.11 (13) and 85.73 (13)°. In the crystal, components are linked by N-H⋯O, O-H⋯S and O-H⋯π inter-actions. There also exist π-π inter-actions with a distance of 3.876 (2) Å between the centroids of benzene rings of two different ligands. Together, the inter-molecular inter-actions lead to a three-dimensional network.

Related literature

For related structures, see: Khan et al. (2007 ▶); Mufakkar et al. (2007 ▶); Zoufalá et al. (2007 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

[CuBr(C13H12N2S)2]·H2O

M = 618.08

Triclinic,

a = 9.6195 (5) Å

b = 12.1937 (6) Å

c = 12.7969 (6) Å

α = 89.345 (2)°

β = 73.154 (1)°

γ = 69.225 (2)°

V = 1336.20 (11) Å3

Z = 2

Mo Kα radiation

μ = 2.50 mm−1

T = 296 K

0.28 × 0.23 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.509, T max = 0.606

27804 measured reflections

6568 independent reflections

5426 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.122

S = 1.04

6568 reflections

316 parameters

H-atom parameters constrained

Δρmax = 0.47 e Å−3

Δρmin = −1.27 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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/S1600536809026038/hb5021sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809026038/hb5021Isup2.hkl

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

[CuBr(C13H12N2S)2]·H2O	Z = 2
Mr = 618.08	F(000) = 628
Triclinic, P1	Dx = 1.536 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.6195 (5) Å	Cell parameters from 6568 reflections
b = 12.1937 (6) Å	θ = 2.3–28.3°
c = 12.7969 (6) Å	µ = 2.50 mm−1
α = 89.345 (2)°	T = 296 K
β = 73.154 (1)°	Prismatic, colourless
γ = 69.225 (2)°	0.28 × 0.23 × 0.20 mm
V = 1336.20 (11) Å3

Bruker Kappa APEXII CCD diffractometer	6568 independent reflections
Radiation source: fine-focus sealed tube	5426 reflections with I > 2σ(I)
graphite	Rint = 0.024
Detector resolution: 7.40 pixels mm-1	θmax = 28.3°, θmin = 2.3°
ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −16→16
Tmin = 0.509, Tmax = 0.606	l = −17→15
27804 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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0609P)2 + 1.6374P] where P = (Fo2 + 2Fc2)/3
6568 reflections	(Δ/σ)max < 0.001
316 parameters	Δρmax = 0.47 e Å−3
0 restraints	Δρmin = −1.27 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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
Br1	0.33324 (5)	0.31120 (3)	0.30610 (3)	0.0533 (1)
Cu1	0.44586 (4)	0.10611 (3)	0.26717 (3)	0.0365 (1)
S1	0.38543 (9)	−0.02233 (6)	0.37916 (6)	0.0371 (2)
S2	0.62984 (9)	0.00799 (6)	0.11533 (5)	0.0363 (2)
N1	0.1849 (3)	−0.0049 (2)	0.57745 (18)	0.0329 (6)
N2	0.2381 (3)	0.1621 (2)	0.52856 (18)	0.0332 (7)
N3	0.7569 (3)	0.0539 (2)	−0.08459 (18)	0.0333 (6)
N4	0.5479 (3)	0.2083 (2)	0.02461 (19)	0.0340 (7)
C1	0.2624 (3)	0.0486 (2)	0.5043 (2)	0.0285 (7)
C2	0.2046 (3)	−0.1261 (2)	0.5679 (2)	0.0296 (7)
C3	0.0747 (4)	−0.1555 (3)	0.5850 (3)	0.0389 (9)
C4	0.0924 (5)	−0.2732 (3)	0.5780 (3)	0.0513 (11)
C5	0.2378 (5)	−0.3602 (3)	0.5535 (4)	0.0632 (13)
C6	0.3667 (5)	−0.3298 (3)	0.5391 (4)	0.0621 (13)
C7	0.3512 (4)	−0.2133 (3)	0.5473 (3)	0.0448 (10)
C8	0.1611 (3)	0.2336 (2)	0.6302 (2)	0.0312 (8)
C9	0.0889 (4)	0.3536 (3)	0.6266 (3)	0.0481 (10)
C10	0.0182 (5)	0.4277 (3)	0.7237 (3)	0.0619 (13)
C11	0.0184 (5)	0.3834 (3)	0.8227 (3)	0.0564 (11)
C12	0.0909 (4)	0.2642 (3)	0.8259 (3)	0.0449 (10)
C13	0.1640 (4)	0.1892 (3)	0.7301 (2)	0.0376 (8)
C14	0.6462 (3)	0.0959 (2)	0.0114 (2)	0.0284 (7)
C15	0.8697 (3)	−0.0636 (3)	−0.1082 (2)	0.0321 (7)
C16	0.8232 (4)	−0.1582 (3)	−0.1121 (3)	0.0410 (9)
C17	0.9331 (5)	−0.2719 (3)	−0.1320 (3)	0.0536 (11)
C18	1.0894 (4)	−0.2896 (3)	−0.1513 (3)	0.0552 (11)
C19	1.1351 (4)	−0.1968 (3)	−0.1499 (3)	0.0533 (10)
C20	1.0255 (3)	−0.0819 (3)	−0.1277 (3)	0.0413 (9)
C21	0.5400 (3)	0.2845 (2)	−0.0615 (2)	0.0337 (8)
C22	0.4526 (4)	0.2811 (3)	−0.1278 (3)	0.0557 (12)
C23	0.4443 (5)	0.3550 (4)	−0.2108 (4)	0.0703 (17)
C24	0.5207 (5)	0.4323 (3)	−0.2251 (3)	0.0628 (14)
C25	0.6103 (5)	0.4334 (4)	−0.1598 (4)	0.0647 (14)
C26	0.6218 (5)	0.3594 (3)	−0.0775 (3)	0.0514 (11)
O1	0.1532 (3)	0.8554 (2)	0.29920 (19)	0.0501 (8)
H1N	0.11673	0.03785	0.63566	0.0395*
H2N	0.27483	0.19654	0.47431	0.0399*
H3	−0.02407	−0.09678	0.60112	0.0466*
H3N	0.76077	0.10051	−0.13542	0.0399*
H4	0.00491	−0.29344	0.59005	0.0615*
H4N	0.48508	0.23679	0.08933	0.0408*
H5	0.24930	−0.43899	0.54660	0.0755*
H6	0.46526	−0.38872	0.52367	0.0746*
H7	0.43836	−0.19341	0.53904	0.0537*
H9	0.08789	0.38413	0.55980	0.0576*
H10	−0.02992	0.50831	0.72171	0.0742*
H11	−0.03026	0.43368	0.88744	0.0678*
H12	0.09072	0.23412	0.89305	0.0539*
H13	0.21504	0.10909	0.73246	0.0452*
H16	0.71862	−0.14548	−0.10142	0.0492*
H17	0.90225	−0.33603	−0.13232	0.0645*
H18	1.16340	−0.36590	−0.16526	0.0663*
H19	1.24041	−0.20984	−0.16395	0.0639*
H20	1.05705	−0.01834	−0.12595	0.0495*
H22	0.39907	0.22959	−0.11736	0.0667*
H23	0.38646	0.35207	−0.25697	0.0844*
H24	0.51177	0.48381	−0.27901	0.0757*
H25	0.66422	0.48465	−0.17083	0.0781*
H26	0.68364	0.36004	−0.03368	0.0618*
H1O	0.22282	0.86957	0.31621	0.0601*
H2O	0.19151	0.78537	0.29707	0.0601*

	U11	U22	U33	U12	U13	U23
Br1	0.0631 (2)	0.0397 (2)	0.0533 (2)	−0.0185 (2)	−0.0129 (2)	0.0145 (2)
Cu1	0.0378 (2)	0.0381 (2)	0.0288 (2)	−0.0137 (2)	−0.0038 (1)	0.0081 (1)
S1	0.0439 (4)	0.0281 (3)	0.0275 (3)	−0.0113 (3)	0.0041 (3)	0.0020 (2)
S2	0.0398 (4)	0.0300 (3)	0.0285 (3)	−0.0075 (3)	−0.0020 (3)	0.0107 (3)
N1	0.0369 (12)	0.0270 (11)	0.0266 (10)	−0.0108 (10)	0.0011 (9)	0.0016 (8)
N2	0.0428 (13)	0.0266 (11)	0.0262 (10)	−0.0131 (10)	−0.0043 (9)	0.0043 (8)
N3	0.0330 (11)	0.0321 (12)	0.0272 (10)	−0.0096 (10)	−0.0013 (9)	0.0078 (9)
N4	0.0356 (12)	0.0284 (11)	0.0280 (11)	−0.0072 (10)	−0.0010 (9)	0.0072 (9)
C1	0.0285 (12)	0.0262 (12)	0.0266 (12)	−0.0073 (10)	−0.0060 (9)	0.0046 (9)
C2	0.0346 (13)	0.0298 (13)	0.0237 (11)	−0.0129 (11)	−0.0065 (10)	0.0062 (9)
C3	0.0377 (15)	0.0432 (16)	0.0379 (15)	−0.0174 (13)	−0.0118 (12)	0.0095 (12)
C4	0.061 (2)	0.055 (2)	0.0535 (19)	−0.0380 (18)	−0.0198 (16)	0.0120 (16)
C5	0.081 (3)	0.0372 (18)	0.070 (2)	−0.0297 (19)	−0.011 (2)	0.0072 (17)
C6	0.052 (2)	0.0324 (17)	0.082 (3)	−0.0068 (15)	−0.0023 (19)	0.0101 (17)
C7	0.0370 (15)	0.0352 (16)	0.0577 (19)	−0.0126 (13)	−0.0093 (14)	0.0148 (14)
C8	0.0323 (13)	0.0262 (13)	0.0332 (13)	−0.0089 (10)	−0.0093 (10)	0.0003 (10)
C9	0.066 (2)	0.0290 (15)	0.0455 (17)	−0.0106 (14)	−0.0203 (16)	0.0045 (12)
C10	0.079 (3)	0.0293 (16)	0.061 (2)	0.0008 (17)	−0.023 (2)	−0.0063 (15)
C11	0.063 (2)	0.0451 (19)	0.0463 (19)	−0.0051 (17)	−0.0126 (16)	−0.0163 (15)
C12	0.0524 (18)	0.0476 (18)	0.0328 (14)	−0.0154 (15)	−0.0138 (13)	0.0001 (13)
C13	0.0428 (16)	0.0317 (14)	0.0340 (14)	−0.0082 (12)	−0.0122 (12)	0.0029 (11)
C14	0.0277 (12)	0.0293 (13)	0.0276 (12)	−0.0115 (10)	−0.0064 (9)	0.0066 (10)
C15	0.0318 (13)	0.0350 (14)	0.0234 (11)	−0.0086 (11)	−0.0040 (10)	0.0025 (10)
C16	0.0389 (15)	0.0413 (16)	0.0409 (16)	−0.0144 (13)	−0.0095 (12)	−0.0046 (12)
C17	0.070 (2)	0.0355 (17)	0.0500 (19)	−0.0156 (16)	−0.0150 (17)	−0.0070 (14)
C18	0.057 (2)	0.0422 (19)	0.0456 (18)	0.0061 (16)	−0.0153 (16)	−0.0076 (14)
C19	0.0344 (16)	0.065 (2)	0.0468 (18)	−0.0018 (15)	−0.0127 (14)	−0.0062 (16)
C20	0.0356 (15)	0.0489 (18)	0.0384 (15)	−0.0164 (13)	−0.0087 (12)	−0.0002 (13)
C21	0.0342 (14)	0.0269 (13)	0.0326 (13)	−0.0080 (11)	−0.0036 (11)	0.0095 (10)
C22	0.060 (2)	0.061 (2)	0.066 (2)	−0.0357 (19)	−0.0326 (19)	0.0340 (19)
C23	0.078 (3)	0.085 (3)	0.071 (3)	−0.041 (3)	−0.044 (2)	0.044 (2)
C24	0.073 (3)	0.051 (2)	0.054 (2)	−0.0160 (19)	−0.0136 (19)	0.0303 (17)
C25	0.087 (3)	0.051 (2)	0.068 (2)	−0.042 (2)	−0.021 (2)	0.0278 (19)
C26	0.067 (2)	0.0484 (19)	0.0520 (19)	−0.0341 (18)	−0.0217 (17)	0.0159 (15)
O1	0.0479 (13)	0.0506 (14)	0.0404 (12)	−0.0115 (11)	−0.0050 (10)	0.0059 (10)

Cu1—Br1	2.3387 (5)	C15—C20	1.380 (5)
Cu1—S1	2.2263 (8)	C16—C17	1.385 (5)
Cu1—S2	2.2129 (8)	C17—C18	1.387 (7)
S1—C1	1.709 (3)	C18—C19	1.354 (5)
S2—C14	1.705 (2)	C19—C20	1.394 (5)
O1—H1O	0.8300	C21—C22	1.367 (5)
O1—H2O	0.8000	C21—C26	1.381 (5)
N1—C1	1.336 (4)	C22—C23	1.387 (6)
N1—C2	1.424 (3)	C23—C24	1.368 (7)
N2—C1	1.343 (3)	C24—C25	1.367 (7)
N2—C8	1.418 (3)	C25—C26	1.382 (6)
N3—C15	1.428 (4)	C3—H3	0.9300
N3—C14	1.332 (3)	C4—H4	0.9300
N4—C14	1.340 (3)	C5—H5	0.9300
N4—C21	1.435 (3)	C6—H6	0.9300
N1—H1N	0.8600	C7—H7	0.9300
N2—H2N	0.8600	C9—H9	0.9300
N3—H3N	0.8600	C10—H10	0.9300
N4—H4N	0.8600	C11—H11	0.9300
C2—C3	1.377 (5)	C12—H12	0.9300
C2—C7	1.384 (5)	C13—H13	0.9300
C3—C4	1.385 (5)	C16—H16	0.9300
C4—C5	1.371 (6)	C17—H17	0.9300
C5—C6	1.379 (7)	C18—H18	0.9300
C6—C7	1.377 (5)	C19—H19	0.9300
C8—C13	1.387 (4)	C20—H20	0.9300
C8—C9	1.386 (4)	C22—H22	0.9300
C9—C10	1.387 (5)	C23—H23	0.9300
C10—C11	1.372 (5)	C24—H24	0.9300
C11—C12	1.377 (5)	C25—H25	0.9300
C12—C13	1.380 (5)	C26—H26	0.9300
C15—C16	1.383 (5)
Br1—Cu1—S1	125.03 (3)	C22—C21—C26	120.7 (3)
Br1—Cu1—S2	126.04 (3)	N4—C21—C26	119.9 (3)
S1—Cu1—S2	108.93 (3)	N4—C21—C22	119.4 (3)
Cu1—S1—C1	110.49 (9)	C21—C22—C23	119.5 (4)
Cu1—S2—C14	111.94 (9)	C22—C23—C24	120.3 (4)
H1O—O1—H2O	96.00	C23—C24—C25	119.7 (4)
C1—N1—C2	126.0 (2)	C24—C25—C26	120.9 (4)
C1—N2—C8	129.7 (2)	C21—C26—C25	118.9 (4)
C14—N3—C15	124.0 (2)	C2—C3—H3	120.00
C14—N4—C21	124.7 (2)	C4—C3—H3	120.00
C1—N1—H1N	117.00	C5—C4—H4	120.00
C2—N1—H1N	117.00	C3—C4—H4	120.00
C8—N2—H2N	115.00	C4—C5—H5	120.00
C1—N2—H2N	115.00	C6—C5—H5	120.00
C14—N3—H3N	118.00	C7—C6—H6	120.00
C15—N3—H3N	118.00	C5—C6—H6	120.00
C21—N4—H4N	118.00	C2—C7—H7	120.00
C14—N4—H4N	118.00	C6—C7—H7	120.00
S1—C1—N2	119.5 (2)	C10—C9—H9	120.00
N1—C1—N2	118.9 (2)	C8—C9—H9	120.00
S1—C1—N1	121.50 (19)	C11—C10—H10	120.00
C3—C2—C7	120.4 (3)	C9—C10—H10	120.00
N1—C2—C3	119.0 (3)	C10—C11—H11	120.00
N1—C2—C7	120.6 (3)	C12—C11—H11	120.00
C2—C3—C4	119.4 (4)	C11—C12—H12	120.00
C3—C4—C5	120.6 (4)	C13—C12—H12	120.00
C4—C5—C6	119.5 (4)	C12—C13—H13	120.00
C5—C6—C7	120.8 (4)	C8—C13—H13	120.00
C2—C7—C6	119.3 (4)	C15—C16—H16	120.00
N2—C8—C9	117.3 (2)	C17—C16—H16	120.00
C9—C8—C13	119.9 (3)	C18—C17—H17	120.00
N2—C8—C13	122.7 (2)	C16—C17—H17	120.00
C8—C9—C10	119.3 (3)	C17—C18—H18	120.00
C9—C10—C11	120.7 (3)	C19—C18—H18	120.00
C10—C11—C12	119.8 (3)	C20—C19—H19	120.00
C11—C12—C13	120.4 (3)	C18—C19—H19	120.00
C8—C13—C12	119.8 (3)	C15—C20—H20	120.00
S2—C14—N3	120.56 (19)	C19—C20—H20	120.00
S2—C14—N4	120.7 (2)	C23—C22—H22	120.00
N3—C14—N4	118.8 (2)	C21—C22—H22	120.00
N3—C15—C16	120.2 (3)	C22—C23—H23	120.00
C16—C15—C20	120.3 (3)	C24—C23—H23	120.00
N3—C15—C20	119.5 (3)	C25—C24—H24	120.00
C15—C16—C17	119.7 (4)	C23—C24—H24	120.00
C16—C17—C18	119.6 (4)	C24—C25—H25	120.00
C17—C18—C19	120.6 (3)	C26—C25—H25	120.00
C18—C19—C20	120.5 (4)	C21—C26—H26	121.00
C15—C20—C19	119.3 (3)	C25—C26—H26	121.00
Br1—Cu1—S1—C1	−7.29 (13)	C2—C3—C4—C5	−0.5 (6)
S2—Cu1—S1—C1	172.19 (12)	C3—C4—C5—C6	2.0 (7)
Br1—Cu1—S2—C14	−17.05 (13)	C4—C5—C6—C7	−1.1 (7)
S1—Cu1—S2—C14	163.48 (12)	C5—C6—C7—C2	−1.4 (6)
Cu1—S1—C1—N1	166.2 (2)	N2—C8—C9—C10	−177.1 (4)
Cu1—S1—C1—N2	−11.3 (3)	C13—C8—C9—C10	−1.0 (6)
Cu1—S2—C14—N3	176.2 (2)	N2—C8—C13—C12	177.9 (3)
Cu1—S2—C14—N4	−4.0 (3)	C9—C8—C13—C12	2.0 (6)
C2—N1—C1—S1	7.0 (4)	C8—C9—C10—C11	−0.4 (7)
C2—N1—C1—N2	−175.5 (3)	C9—C10—C11—C12	0.7 (7)
C1—N1—C2—C3	−130.1 (3)	C10—C11—C12—C13	0.3 (7)
C1—N1—C2—C7	53.2 (4)	C11—C12—C13—C8	−1.6 (6)
C8—N2—C1—S1	−169.9 (3)	N3—C15—C16—C17	−178.2 (3)
C8—N2—C1—N1	12.6 (5)	C20—C15—C16—C17	2.2 (5)
C1—N2—C8—C9	−150.7 (4)	N3—C15—C20—C19	179.5 (3)
C1—N2—C8—C13	33.2 (5)	C16—C15—C20—C19	−0.9 (5)
C15—N3—C14—S2	−1.0 (4)	C15—C16—C17—C18	−2.1 (5)
C15—N3—C14—N4	179.1 (3)	C16—C17—C18—C19	0.6 (6)
C14—N3—C15—C16	66.0 (4)	C17—C18—C19—C20	0.8 (6)
C14—N3—C15—C20	−114.4 (4)	C18—C19—C20—C15	−0.7 (5)
C21—N4—C14—S2	−172.0 (2)	N4—C21—C22—C23	179.8 (3)
C21—N4—C14—N3	7.9 (5)	C26—C21—C22—C23	−1.0 (5)
C14—N4—C21—C22	84.2 (4)	N4—C21—C26—C25	−178.9 (3)
C14—N4—C21—C26	−95.1 (4)	C22—C21—C26—C25	1.8 (5)
N1—C2—C3—C4	−178.8 (3)	C21—C22—C23—C24	−1.2 (6)
C7—C2—C3—C4	−2.0 (5)	C22—C23—C24—C25	2.5 (7)
N1—C2—C7—C6	179.6 (3)	C23—C24—C25—C26	−1.6 (7)
C3—C2—C7—C6	3.0 (5)	C24—C25—C26—C21	−0.5 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.86	2.35	3.046 (4)	139
O1—H1O···S1ii	0.83	2.66	3.462 (3)	163
N2—H2N···Br1	0.86	2.59	3.435 (2)	169
N3—H3N···O1iii	0.86	2.16	2.957 (3)	155
N4—H4N···Br1	0.86	2.72	3.573 (2)	170
C13—H13···N1	0.93	2.58	3.000 (4)	108
C13—H13···S2iv	0.93	2.86	3.523 (3)	129
O1—H2O···CgDiii	0.80	2.78	3.306 (3)	125

Cu1—Br1	2.3387 (5)
Cu1—S1	2.2263 (8)
Cu1—S2	2.2129 (8)

Br1—Cu1—S1	125.03 (3)
Br1—Cu1—S2	126.04 (3)
S1—Cu1—S2	108.93 (3)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.86	2.35	3.046 (4)	139
O1—H1O⋯S1ii	0.83	2.66	3.462 (3)	163
N2—H2N⋯Br1	0.86	2.59	3.435 (2)	169
N3—H3N⋯O1iii	0.86	2.16	2.957 (3)	155
N4—H4N⋯Br1	0.86	2.72	3.573 (2)	170
C13—H13⋯N1	0.93	2.58	3.000 (4)	108
C13—H13⋯S2iv	0.93	2.86	3.523 (3)	129
O1—H2O⋯CgDiii	0.80	2.78	3.306 (3)	125

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) . CgD is the centroid of the C21–C26 benzene ring.