2-(8-Bromo-imidazo[1,2-a]pyridin-2-yl)-N'-[(E)-4-diethyl-amino-2-hy-droxy-benzyl-idene]acetohydrazide dihydrate.

In the title compound, C(20)H(22)BrN(5)O(2)·2H(2)O, the Schiff base mol-ecule exists in an E conformation with respect to the acyclic C=N bond. An S(6) ring motif is formed via an intra-molecular O-H⋯N hydrogen bond. The dihedral angle between the imidazo[1,2-a]pyridine system and the benzene ring is 84.62 (5)°. In the crystal, N-H⋯O, O-H⋯O, O-H⋯N, C-H⋯O and C-H⋯Br hydrogen bonds link the mol-ecules into a three-dimensional network. The crystal packing is further stabilized by C-H⋯π and π-π inter-actions [centroid-centroid distance = 3.5365 (7) Å].

Related literature

For background to and applications of hydrazones, see: Seleem et al. (2011 ▶); Rollas & Küçükgüzel (2007 ▶). For background to and applications of n class="Chemical">imidazopyridine, see: Ertepinarl et al. (1995 ▶); Liang et al. (2007 ▶); Hamdouchi et al. (1999 ▶); Gudmundsson & Johns (2007 ▶); Biftu et al. (2006 ▶); Fisher & Lusi (1972 ▶); Bochis et al. (1981 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C20H22BrN5O2·2H2O

M = 480.37

Triclinic,

a = 8.4370 (4) Å

b = 10.6711 (5) Å

c = 11.7559 (5) Å

α = 92.914 (1)°

β = 96.949 (1)°

γ = 93.978 (1)°

V = 1046.23 (8) Å3

Z = 2

Mo Kα radiation

μ = 2.00 mm−1

T = 100 K

0.37 × 0.20 × 0.07 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.529, T max = 0.869

22937 measured reflections

6491 independent reflections

5841 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.077

S = 1.05

6491 reflections

297 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.63 e Å−3

Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681200685X/bq2340sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681200685X/bq2340Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681200685X/bq2340Isup3.cml

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

C20H22BrN5O2·2H2O	Z = 2
Mr = 480.37	F(000) = 496
Triclinic, P1	Dx = 1.525 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.4370 (4) Å	Cell parameters from 9983 reflections
b = 10.6711 (5) Å	θ = 2.4–30.9°
c = 11.7559 (5) Å	µ = 2.00 mm−1
α = 92.914 (1)°	T = 100 K
β = 96.949 (1)°	Plate, orange
γ = 93.978 (1)°	0.37 × 0.20 × 0.07 mm
V = 1046.23 (8) Å3

Bruker SMART APEXII CCD diffractometer	6491 independent reflections
Radiation source: fine-focus sealed tube	5841 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
φ and ω scans	θmax = 30.9°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −12→12
Tmin = 0.529, Tmax = 0.869	k = −15→15
22937 measured reflections	l = −16→16

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.077	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0455P)2 + 0.2952P] where P = (Fo2 + 2Fc2)/3
6491 reflections	(Δ/σ)max = 0.002
297 parameters	Δρmax = 0.63 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
Br1	0.789019 (15)	0.424051 (13)	0.748329 (12)	0.02141 (5)
O1	−0.05933 (11)	0.23815 (10)	0.52050 (9)	0.02047 (19)
O2	−0.26058 (13)	0.04472 (10)	0.79255 (9)	0.0227 (2)
N1	0.44340 (12)	0.35221 (10)	0.59413 (9)	0.01348 (19)
N2	0.35279 (12)	0.54369 (10)	0.61740 (9)	0.01344 (19)
N3	0.10753 (13)	0.09994 (10)	0.60467 (9)	0.01444 (19)
N4	−0.00110 (13)	0.05569 (10)	0.67606 (9)	0.0150 (2)
N5	−0.25929 (13)	−0.22618 (11)	1.10154 (9)	0.0164 (2)
C1	0.47756 (14)	0.46769 (11)	0.64404 (10)	0.0127 (2)
C2	0.61422 (15)	0.52232 (12)	0.71616 (11)	0.0147 (2)
C3	0.62011 (16)	0.64472 (13)	0.75761 (11)	0.0174 (2)
H3A	0.7093	0.6799	0.8059	0.021*
C4	0.48898 (17)	0.71799 (12)	0.72639 (11)	0.0182 (2)
H4A	0.4935	0.8015	0.7542	0.022*
C5	0.35760 (16)	0.66812 (12)	0.65681 (11)	0.0175 (2)
H5A	0.2725	0.7167	0.6361	0.021*
C6	0.23518 (14)	0.47094 (12)	0.54616 (11)	0.0153 (2)
H6A	0.1371	0.4957	0.5135	0.018*
C7	0.29303 (14)	0.35486 (12)	0.53359 (10)	0.0134 (2)
C8	0.20850 (15)	0.23836 (12)	0.46996 (11)	0.0155 (2)
H8A	0.2831	0.1737	0.4649	0.019*
H8B	0.1674	0.2574	0.3926	0.019*
C9	0.07088 (14)	0.19108 (12)	0.53330 (11)	0.0143 (2)
C10	0.05212 (15)	−0.02976 (12)	0.74143 (11)	0.0158 (2)
H10A	0.1519	−0.0582	0.7326	0.019*
C11	−0.03602 (15)	−0.08324 (12)	0.82756 (11)	0.0146 (2)
C12	0.03051 (15)	−0.17581 (13)	0.89465 (12)	0.0175 (2)
H12A	0.1274	−0.2048	0.8788	0.021*
C13	−0.04169 (15)	−0.22574 (12)	0.98328 (11)	0.0173 (2)
H13A	0.0055	−0.2883	1.0247	0.021*
C14	−0.18834 (15)	−0.18158 (12)	1.01136 (10)	0.0144 (2)
C15	−0.25764 (15)	−0.08989 (12)	0.94303 (11)	0.0156 (2)
H15A	−0.3549	−0.0610	0.9582	0.019*
C16	−0.18382 (15)	−0.04205 (12)	0.85370 (11)	0.0147 (2)
C17	−0.19118 (17)	−0.32564 (13)	1.16815 (12)	0.0196 (2)
H17A	−0.2326	−0.3243	1.2416	0.024*
H17B	−0.0760	−0.3076	1.1831	0.024*
C18	−0.2262 (2)	−0.45760 (14)	1.11027 (14)	0.0265 (3)
H18A	−0.1691	−0.5164	1.1555	0.040*
H18B	−0.1926	−0.4586	1.0351	0.040*
H18C	−0.3391	−0.4808	1.1038	0.040*
C19	−0.41481 (16)	−0.18615 (13)	1.12605 (11)	0.0186 (2)
H19A	−0.4149	−0.0958	1.1202	0.022*
H19B	−0.4286	−0.2039	1.2045	0.022*
C20	−0.55683 (17)	−0.25000 (16)	1.04598 (13)	0.0252 (3)
H20A	−0.6542	−0.2176	1.0652	0.038*
H20B	−0.5615	−0.3391	1.0544	0.038*
H20C	−0.5440	−0.2334	0.9680	0.038*
O1W	0.64543 (12)	0.15365 (9)	0.57170 (9)	0.01893 (19)
O2W	0.60246 (12)	0.01353 (10)	0.36855 (10)	0.01989 (19)
H1N3	0.205 (2)	0.0710 (17)	0.6120 (15)	0.018 (4)*
H1O2	−0.209 (3)	0.069 (3)	0.737 (2)	0.058 (8)*
H1W1	0.587 (3)	0.215 (2)	0.582 (2)	0.041 (6)*
H2W1	0.742 (3)	0.181 (2)	0.5720 (18)	0.031 (5)*
H1W2	0.518 (3)	−0.026 (2)	0.369 (2)	0.041 (6)*
H2W2	0.608 (2)	0.060 (2)	0.4315 (18)	0.026 (5)*

	U11	U22	U33	U12	U13	U23
Br1	0.01455 (7)	0.02522 (8)	0.02311 (8)	0.00475 (5)	−0.00432 (5)	−0.00016 (5)
O1	0.0123 (4)	0.0243 (5)	0.0255 (5)	0.0016 (3)	0.0027 (4)	0.0083 (4)
O2	0.0220 (5)	0.0254 (5)	0.0236 (5)	0.0075 (4)	0.0069 (4)	0.0106 (4)
N1	0.0117 (4)	0.0156 (5)	0.0132 (5)	0.0004 (4)	0.0019 (4)	0.0016 (4)
N2	0.0121 (4)	0.0152 (5)	0.0133 (5)	0.0009 (3)	0.0018 (4)	0.0027 (4)
N3	0.0107 (4)	0.0166 (5)	0.0165 (5)	−0.0009 (4)	0.0041 (4)	0.0021 (4)
N4	0.0126 (4)	0.0178 (5)	0.0147 (5)	−0.0017 (4)	0.0037 (4)	0.0009 (4)
N5	0.0165 (5)	0.0194 (5)	0.0136 (5)	0.0012 (4)	0.0030 (4)	0.0031 (4)
C1	0.0115 (5)	0.0154 (5)	0.0115 (5)	0.0013 (4)	0.0022 (4)	0.0031 (4)
C2	0.0130 (5)	0.0177 (6)	0.0131 (5)	0.0007 (4)	0.0007 (4)	0.0020 (4)
C3	0.0179 (6)	0.0194 (6)	0.0138 (5)	−0.0021 (4)	0.0005 (4)	0.0001 (4)
C4	0.0229 (6)	0.0151 (5)	0.0167 (6)	0.0017 (4)	0.0036 (5)	0.0013 (4)
C5	0.0199 (6)	0.0156 (6)	0.0178 (6)	0.0040 (4)	0.0036 (5)	0.0036 (4)
C6	0.0109 (5)	0.0197 (6)	0.0148 (5)	0.0000 (4)	−0.0001 (4)	0.0026 (4)
C7	0.0118 (5)	0.0171 (5)	0.0115 (5)	−0.0009 (4)	0.0030 (4)	0.0024 (4)
C8	0.0136 (5)	0.0188 (6)	0.0140 (5)	−0.0030 (4)	0.0039 (4)	0.0004 (4)
C9	0.0122 (5)	0.0160 (5)	0.0141 (5)	−0.0030 (4)	0.0017 (4)	0.0001 (4)
C10	0.0129 (5)	0.0173 (6)	0.0169 (6)	−0.0007 (4)	0.0024 (4)	0.0003 (4)
C11	0.0131 (5)	0.0164 (5)	0.0139 (5)	−0.0013 (4)	0.0010 (4)	0.0009 (4)
C12	0.0132 (5)	0.0200 (6)	0.0193 (6)	0.0014 (4)	0.0017 (4)	0.0029 (5)
C13	0.0154 (5)	0.0187 (6)	0.0176 (6)	0.0012 (4)	0.0004 (4)	0.0041 (4)
C14	0.0155 (5)	0.0152 (5)	0.0113 (5)	−0.0022 (4)	−0.0003 (4)	−0.0002 (4)
C15	0.0145 (5)	0.0173 (6)	0.0152 (6)	0.0010 (4)	0.0023 (4)	0.0007 (4)
C16	0.0144 (5)	0.0150 (5)	0.0144 (5)	−0.0004 (4)	0.0008 (4)	0.0007 (4)
C17	0.0227 (6)	0.0207 (6)	0.0158 (6)	0.0017 (5)	0.0024 (5)	0.0040 (5)
C18	0.0312 (8)	0.0201 (7)	0.0288 (8)	0.0007 (5)	0.0058 (6)	0.0029 (5)
C19	0.0193 (6)	0.0230 (6)	0.0145 (6)	0.0023 (5)	0.0055 (5)	0.0016 (5)
C20	0.0177 (6)	0.0342 (8)	0.0235 (7)	−0.0006 (5)	0.0040 (5)	−0.0005 (6)
O1W	0.0137 (4)	0.0173 (4)	0.0263 (5)	0.0007 (3)	0.0043 (4)	0.0026 (4)
O2W	0.0150 (4)	0.0182 (4)	0.0270 (5)	0.0005 (3)	0.0057 (4)	0.0000 (4)

Br1—C2	1.8809 (13)	C8—H8B	0.9700
O1—C9	1.2354 (16)	C10—C11	1.4444 (17)
O2—C16	1.3534 (16)	C10—H10A	0.9300
O2—H1O2	0.87 (3)	C11—C12	1.4007 (18)
N1—C1	1.3350 (16)	C11—C16	1.4134 (17)
N1—C7	1.3804 (16)	C12—C13	1.3804 (18)
N2—C5	1.3802 (16)	C12—H12A	0.9300
N2—C6	1.3837 (16)	C13—C14	1.4232 (18)
N2—C1	1.3887 (15)	C13—H13A	0.9300
N3—C9	1.3443 (17)	C14—C15	1.4108 (17)
N3—N4	1.3906 (14)	C15—C16	1.3856 (18)
N3—H1N3	0.896 (19)	C15—H15A	0.9300
N4—C10	1.2915 (17)	C17—C18	1.526 (2)
N5—C14	1.3690 (16)	C17—H17A	0.9700
N5—C17	1.4594 (17)	C17—H17B	0.9700
N5—C19	1.4642 (17)	C18—H18A	0.9600
C1—C2	1.4170 (17)	C18—H18B	0.9600
C2—C3	1.3662 (18)	C18—H18C	0.9600
C3—C4	1.4216 (19)	C19—C20	1.528 (2)
C3—H3A	0.9300	C19—H19A	0.9700
C4—C5	1.3548 (19)	C19—H19B	0.9700
C4—H4A	0.9300	C20—H20A	0.9600
C5—H5A	0.9300	C20—H20B	0.9600
C6—C7	1.3701 (17)	C20—H20C	0.9600
C6—H6A	0.9300	O1W—H1W1	0.86 (3)
C7—C8	1.5057 (17)	O1W—H2W1	0.84 (2)
C8—C9	1.5242 (17)	O2W—H1W2	0.80 (3)
C8—H8A	0.9700	O2W—H2W2	0.86 (2)
C16—O2—H1O2	111.7 (18)	C12—C11—C16	116.99 (11)
C1—N1—C7	105.16 (10)	C12—C11—C10	119.37 (11)
C5—N2—C6	130.13 (11)	C16—C11—C10	123.53 (12)
C5—N2—C1	123.09 (11)	C13—C12—C11	122.76 (12)
C6—N2—C1	106.77 (10)	C13—C12—H12A	118.6
C9—N3—N4	120.60 (10)	C11—C12—H12A	118.6
C9—N3—H1N3	121.0 (12)	C12—C13—C14	120.09 (12)
N4—N3—H1N3	118.2 (12)	C12—C13—H13A	120.0
C10—N4—N3	113.55 (10)	C14—C13—H13A	120.0
C14—N5—C17	120.87 (11)	N5—C14—C15	121.23 (11)
C14—N5—C19	121.09 (11)	N5—C14—C13	121.24 (12)
C17—N5—C19	117.68 (11)	C15—C14—C13	117.54 (11)
N1—C1—N2	111.09 (10)	C16—C15—C14	121.34 (12)
N1—C1—C2	131.60 (11)	C16—C15—H15A	119.3
N2—C1—C2	117.31 (11)	C14—C15—H15A	119.3
C3—C2—C1	120.47 (12)	O2—C16—C15	116.85 (11)
C3—C2—Br1	121.18 (10)	O2—C16—C11	121.89 (12)
C1—C2—Br1	118.31 (9)	C15—C16—C11	121.25 (12)
C2—C3—C4	119.53 (12)	N5—C17—C18	114.42 (12)
C2—C3—H3A	120.2	N5—C17—H17A	108.7
C4—C3—H3A	120.2	C18—C17—H17A	108.7
C5—C4—C3	121.06 (12)	N5—C17—H17B	108.7
C5—C4—H4A	119.5	C18—C17—H17B	108.7
C3—C4—H4A	119.5	H17A—C17—H17B	107.6
C4—C5—N2	118.52 (12)	C17—C18—H18A	109.5
C4—C5—H5A	120.7	C17—C18—H18B	109.5
N2—C5—H5A	120.7	H18A—C18—H18B	109.5
C7—C6—N2	105.77 (11)	C17—C18—H18C	109.5
C7—C6—H6A	127.1	H18A—C18—H18C	109.5
N2—C6—H6A	127.1	H18B—C18—H18C	109.5
C6—C7—N1	111.22 (11)	N5—C19—C20	113.89 (11)
C6—C7—C8	127.58 (11)	N5—C19—H19A	108.8
N1—C7—C8	121.11 (11)	C20—C19—H19A	108.8
C7—C8—C9	109.35 (10)	N5—C19—H19B	108.8
C7—C8—H8A	109.8	C20—C19—H19B	108.8
C9—C8—H8A	109.8	H19A—C19—H19B	107.7
C7—C8—H8B	109.8	C19—C20—H20A	109.5
C9—C8—H8B	109.8	C19—C20—H20B	109.5
H8A—C8—H8B	108.3	H20A—C20—H20B	109.5
O1—C9—N3	124.94 (11)	C19—C20—H20C	109.5
O1—C9—C8	120.90 (12)	H20A—C20—H20C	109.5
N3—C9—C8	114.12 (11)	H20B—C20—H20C	109.5
N4—C10—C11	123.10 (12)	H1W1—O1W—H2W1	110 (2)
N4—C10—H10A	118.5	H1W2—O2W—H2W2	101 (2)
C11—C10—H10A	118.5
C9—N3—N4—C10	−178.57 (11)	C7—C8—C9—O1	81.70 (15)
C7—N1—C1—N2	0.28 (13)	C7—C8—C9—N3	−95.99 (13)
C7—N1—C1—C2	−179.63 (13)	N3—N4—C10—C11	175.89 (11)
C5—N2—C1—N1	−179.26 (11)	N4—C10—C11—C12	179.87 (12)
C6—N2—C1—N1	−0.44 (13)	N4—C10—C11—C16	−4.1 (2)
C5—N2—C1—C2	0.66 (17)	C16—C11—C12—C13	−0.39 (19)
C6—N2—C1—C2	179.48 (11)	C10—C11—C12—C13	175.88 (12)
N1—C1—C2—C3	−179.62 (13)	C11—C12—C13—C14	−1.3 (2)
N2—C1—C2—C3	0.47 (18)	C17—N5—C14—C15	176.84 (12)
N1—C1—C2—Br1	2.65 (19)	C19—N5—C14—C15	3.84 (18)
N2—C1—C2—Br1	−177.26 (8)	C17—N5—C14—C13	−3.34 (18)
C1—C2—C3—C4	−1.02 (19)	C19—N5—C14—C13	−176.34 (12)
Br1—C2—C3—C4	176.64 (10)	C12—C13—C14—N5	−177.55 (12)
C2—C3—C4—C5	0.5 (2)	C12—C13—C14—C15	2.28 (19)
C3—C4—C5—N2	0.6 (2)	N5—C14—C15—C16	178.18 (12)
C6—N2—C5—C4	−179.72 (12)	C13—C14—C15—C16	−1.64 (18)
C1—N2—C5—C4	−1.20 (19)	C14—C15—C16—O2	179.42 (11)
C5—N2—C6—C7	179.12 (12)	C14—C15—C16—C11	−0.03 (19)
C1—N2—C6—C7	0.41 (13)	C12—C11—C16—O2	−178.35 (12)
N2—C6—C7—N1	−0.25 (14)	C10—C11—C16—O2	5.54 (19)
N2—C6—C7—C8	176.21 (11)	C12—C11—C16—C15	1.06 (18)
C1—N1—C7—C6	−0.01 (14)	C10—C11—C16—C15	−175.04 (12)
C1—N1—C7—C8	−176.73 (11)	C14—N5—C17—C18	−78.07 (16)
C6—C7—C8—C9	−68.28 (16)	C19—N5—C17—C18	95.16 (14)
N1—C7—C8—C9	107.87 (13)	C14—N5—C19—C20	77.22 (16)
N4—N3—C9—O1	−3.51 (19)	C17—N5—C19—C20	−96.00 (14)
N4—N3—C9—C8	174.06 (10)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1N3···O2Wi	0.894 (17)	1.908 (17)	2.7956 (15)	171.7 (17)
O2—H1O2···O1Wii	0.87 (3)	2.42 (3)	2.9423 (15)	119 (2)
O2—H1O2···N4	0.87 (3)	1.99 (3)	2.7181 (16)	142 (2)
O1W—H1W1···N1	0.86 (2)	1.98 (2)	2.8315 (14)	176 (2)
O1W—H2W1···O1iii	0.85 (3)	1.92 (2)	2.7361 (14)	162 (2)
O2W—H1W2···O1Wi	0.80 (2)	2.08 (2)	2.8311 (15)	157 (2)
O2W—H2W2···O1W	0.86 (2)	1.87 (2)	2.7245 (15)	172.9 (17)
C5—H5A···O1iv	0.93	2.50	3.3121 (17)	146
C10—H10A···O2Wi	0.93	2.54	3.3256 (17)	142
C17—H17B···Br1v	0.97	2.85	3.6569 (15)	142
C3—H3A···Cg3vi	0.93	2.61	3.4734 (15)	154
C17—H17A···Cg1vii	0.97	2.70	3.5863 (15)	152

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N1/C1/N2/C6/C7 ring and Cg3 is the centroid of the C11–C16 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H1N3⋯O2Wi	0.894 (17)	1.908 (17)	2.7956 (15)	171.7 (17)
O2—H1O2⋯O1Wii	0.87 (3)	2.42 (3)	2.9423 (15)	119 (2)
O2—H1O2⋯N4	0.87 (3)	1.99 (3)	2.7181 (16)	142 (2)
O1W—H1W1⋯N1	0.86 (2)	1.98 (2)	2.8315 (14)	176 (2)
O1W—H2W1⋯O1iii	0.85 (3)	1.92 (2)	2.7361 (14)	162 (2)
O2W—H1W2⋯O1Wi	0.80 (2)	2.08 (2)	2.8311 (15)	157 (2)
O2W—H2W2⋯O1W	0.86 (2)	1.87 (2)	2.7245 (15)	172.9 (17)
C5—H5A⋯O1iv	0.93	2.50	3.3121 (17)	146
C10—H10A⋯O2Wi	0.93	2.54	3.3256 (17)	142
C17—H17B⋯Br1v	0.97	2.85	3.6569 (15)	142
C3—H3A⋯Cg3vi	0.93	2.61	3.4734 (15)	154
C17—H17A⋯Cg1vii	0.97	2.70	3.5863 (15)	152

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) .