2,3,9,10,15,16-Hexaaza­tetra­cyclo­[6.6.2.04,16.011,15]hexa­decane dihydrate

How, F.N.-F.; Rahima, Z.A.; Tan, Y.S.; Abdul Halim, S.N.; Ng, S.W.

doi:10.1107/S1600536812030735

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 8| August 2012| Page o2545

https://doi.org/10.1107/S1600536812030735

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2,3,9,10,15,16-Hexaazatetracyclo[6.6.2.0^4,16.0^11,15]hexadecane dihydrate

Fiona N.-F. How,^a Z. A. Rahima,^a Yee Seng Tan,^b S. Nadiah Abdul Halim ^b ^* and Seik Weng Ng ^b,^c

^aDepartment of Biotechnology, Kulliyyah of Science, International Islamic University Malaysia, 25200 Kuantan, Pahang Darul Makmur, Malaysia, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: nadiahhalim@@um.edu.my

(Received 5 July 2012; accepted 5 July 2012; online 25 July 2012)

The four six-membered fused rings in the title compound, C₁₀H₂₀N₆·2H₂O, adopt chair conformations; the H atoms of the four secondary N atoms occupy axial positions. Hydrogen bonds of the types N—H⋯N, N—H⋯O and O—H⋯N link the organic and water molecules into a three-dimensional network.

Related literature

For background to the reaction of glutaraldehyde and monosubstituted hydrazines, see: Katritzky & Fan (1990 ).

Experimental

Crystal data

C₁₀H₂₀N₆·2H₂O
M_r = 260.35
Monoclinic, P 2₁ /c
a = 9.5154 (10) Å
b = 16.0667 (17) Å
c = 9.1097 (10) Å
β = 114.916 (1)°
V = 1263.1 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 K
0.20 × 0.20 × 0.05 mm

Data collection

Bruker SMART APEX diffractometer
14226 measured reflections
2896 independent reflections
2138 reflections with I > 2σ(I)
R_int = 0.048

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.116
S = 1.02
2896 reflections
195 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H11⋯N3ⁱ	0.93 (3)	1.99 (3)	2.922 (2)	174 (2)
O1W—H12⋯N5ⁱⁱ	0.92 (3)	2.05 (3)	2.960 (2)	178 (2)
O2W—H21⋯N2	0.88 (3)	2.05 (3)	2.925 (2)	172 (2)
O2W—H22⋯N4ⁱⁱ	0.86 (3)	2.02 (3)	2.863 (2)	167 (2)
N1—H1⋯O1W	0.88 (2)	2.08 (2)	2.964 (2)	175 (2)
N2—H2⋯O2Wⁱⁱⁱ	0.91 (2)	2.18 (2)	3.071 (2)	166 (2)
N4—H4⋯N5^iv	0.87 (2)	2.57 (2)	3.354 (2)	150.1 (15)
N5—H5⋯N1ⁱⁱⁱ	0.96 (2)	2.25 (2)	3.163 (2)	159 (2)
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x, y, z+1; (iii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iv) -x+1, -y+1, -z.

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812030735/bt5969sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812030735/bt5969Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812030735/bt5969Isup3.cml

checkCIF report

Comment top

Glutaraldehyde, CH═O(CH₂)₃CH═O, condenses with mono-substituted hydrazines to yield N-substituted piperidines; for example, it reacts with phenylhydrazine to yield N-phenylpiperidin-1-amine (Katritzky & Fan, 1990). The direct reaction of the di-aldehyde with hydrazine itself does not lead to the formation of a polymeric Schiff-base product; the compound is, in fact, 2,3,9,10,15,16-hexaazatetracyclo[6,2,0^4,16.0^11,15]hexadecane, which crystallizes as a dihydrate (Scheme I). The four six-membered fused rings adopt chair conformations (Fig. 1). Hydrogen bonds of the type N–H···N, N–H···O and O–H···N link the organic and water molecules into a three dimensional network (Table 1).

There is no precedent for the fused-ring system in the crystallographic literature.

Related literature top

For background to the reaction of glutaraldehyde and monosubstituted hydrazines, see: Katritzky & Fan (1990).

Experimental top

Hydrazine hydrate (0.08 mol, 2.7 ml) was added to glutaraldehyde (0.08 g, 8.1 ml) to give a white solid. and stirred at room temperature to yield a white solid. This was recrystallized from ethanol; several drops of DMSO was added to aid crystallization.

Structure description top

There is no precedent for the fused-ring system in the crystallographic literature.

For background to the reaction of glutaraldehyde and monosubstituted hydrazines, see: Katritzky & Fan (1990).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) of C₁₀H₂₀N₆^.2H₂O at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

2,3,9,10,15,16-Hexaazatetracyclo[6.6.2.0^4,16.0^11,15]hexadecane dihydrate top

Crystal data top

C₁₀H₂₀N₆·2H₂O	F(000) = 568
M_r = 260.35	D_x = 1.369 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2285 reflections
a = 9.5154 (10) Å	θ = 2.3–30.0°
b = 16.0667 (17) Å	µ = 0.10 mm⁻¹
c = 9.1097 (10) Å	T = 100 K
β = 114.916 (1)°	Prism, colorless
V = 1263.1 (2) Å³	0.20 × 0.20 × 0.05 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	2138 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.048
Graphite monochromator	θ_max = 27.5°, θ_min = 2.5°
ω scans	h = −12→12
14226 measured reflections	k = −20→20
2896 independent reflections	l = −11→11

Refinement top

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0493P)² + 0.6276P] where P = (F_o² + 2F_c²)/3
2896 reflections	(Δ/σ)_max = 0.001
195 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₀H₂₀N₆·2H₂O	V = 1263.1 (2) Å³
M_r = 260.35	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.5154 (10) Å	µ = 0.10 mm⁻¹
b = 16.0667 (17) Å	T = 100 K
c = 9.1097 (10) Å	0.20 × 0.20 × 0.05 mm
β = 114.916 (1)°

Data collection top

Bruker SMART APEX diffractometer	2138 reflections with I > 2σ(I)
14226 measured reflections	R_int = 0.048
2896 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.31 e Å⁻³
2896 reflections	Δρ_min = −0.23 e Å⁻³
195 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1W	0.34037 (14)	0.59785 (8)	0.67888 (15)	0.0195 (3)
O2W	0.75367 (14)	0.67859 (7)	0.93500 (16)	0.0182 (3)
N1	0.47258 (15)	0.70228 (8)	0.49990 (16)	0.0129 (3)
N2	0.63553 (16)	0.68083 (8)	0.58207 (16)	0.0134 (3)
N3	0.60274 (15)	0.57645 (8)	0.36983 (15)	0.0115 (3)
N4	0.61057 (16)	0.59177 (9)	0.11065 (16)	0.0138 (3)
N5	0.44386 (15)	0.60328 (8)	0.03409 (16)	0.0136 (3)
N6	0.43683 (15)	0.59445 (8)	0.30232 (15)	0.0111 (3)
C1	0.66679 (19)	0.59553 (9)	0.54388 (18)	0.0132 (3)
H1A	0.6175	0.5564	0.5937	0.016*
C2	0.84013 (19)	0.57828 (10)	0.6218 (2)	0.0170 (4)
H2A	0.8576	0.5176	0.6203	0.020*
H2B	0.8837	0.5965	0.7362	0.020*
C3	0.92503 (19)	0.62308 (10)	0.5346 (2)	0.0177 (4)
H3A	0.9182	0.6840	0.5462	0.021*
H3B	1.0358	0.6071	0.5839	0.021*
C4	0.85215 (18)	0.59957 (10)	0.3555 (2)	0.0166 (3)
H4A	0.9039	0.6307	0.2984	0.020*
H4B	0.8673	0.5394	0.3439	0.020*
C5	0.68021 (18)	0.61943 (9)	0.27960 (18)	0.0128 (3)
H5A	0.6657	0.6809	0.2837	0.015*
C6	0.36997 (18)	0.56712 (10)	0.13338 (19)	0.0130 (3)
H6	0.3851	0.5055	0.1344	0.016*
C7	0.19610 (19)	0.58261 (10)	0.0546 (2)	0.0168 (4)
H7A	0.1451	0.5442	0.1021	0.020*
H7B	0.1556	0.5703	−0.0626	0.020*
C8	0.15525 (19)	0.67222 (10)	0.0773 (2)	0.0170 (4)
H8A	0.1920	0.7104	0.0157	0.020*
H8B	0.0414	0.6781	0.0353	0.020*
C9	0.23099 (19)	0.69524 (10)	0.25679 (19)	0.0156 (3)
H9A	0.2083	0.7542	0.2700	0.019*
H9B	0.1867	0.6604	0.3165	0.019*
C10	0.40528 (18)	0.68252 (9)	0.32748 (18)	0.0125 (3)
H10A	0.4508	0.7199	0.2711	0.015*
H1	0.427 (2)	0.6716 (12)	0.548 (2)	0.018 (5)*
H2	0.687 (2)	0.7182 (13)	0.547 (2)	0.023 (5)*
H4	0.629 (2)	0.5389 (14)	0.108 (2)	0.027 (5)*
H5	0.427 (2)	0.6621 (13)	0.024 (2)	0.024 (5)*
H11	0.364 (3)	0.5434 (17)	0.661 (3)	0.053 (7)*
H12	0.371 (3)	0.5987 (15)	0.789 (3)	0.051 (7)*
H21	0.711 (3)	0.6761 (14)	0.829 (3)	0.039 (7)*
H22	0.704 (3)	0.6475 (15)	0.974 (3)	0.045 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1W	0.0256 (7)	0.0162 (6)	0.0178 (6)	0.0021 (5)	0.0100 (5)	0.0008 (5)
O2W	0.0192 (7)	0.0204 (6)	0.0158 (6)	−0.0034 (5)	0.0083 (5)	−0.0005 (5)
N1	0.0130 (7)	0.0144 (7)	0.0120 (6)	0.0006 (5)	0.0060 (6)	−0.0009 (5)
N2	0.0135 (7)	0.0115 (6)	0.0147 (7)	−0.0002 (5)	0.0054 (6)	−0.0009 (5)
N3	0.0114 (7)	0.0122 (6)	0.0118 (6)	0.0001 (5)	0.0057 (5)	0.0003 (5)
N4	0.0162 (7)	0.0121 (7)	0.0137 (7)	0.0023 (5)	0.0070 (6)	−0.0006 (5)
N5	0.0149 (7)	0.0134 (7)	0.0128 (7)	0.0014 (5)	0.0060 (6)	0.0006 (5)
N6	0.0106 (6)	0.0101 (6)	0.0117 (6)	0.0007 (5)	0.0040 (5)	−0.0005 (5)
C1	0.0166 (8)	0.0111 (7)	0.0119 (7)	−0.0001 (6)	0.0060 (6)	−0.0002 (6)
C2	0.0162 (8)	0.0156 (8)	0.0163 (8)	0.0016 (6)	0.0041 (7)	−0.0002 (6)
C3	0.0121 (8)	0.0171 (8)	0.0220 (9)	0.0017 (6)	0.0055 (7)	0.0011 (6)
C4	0.0142 (8)	0.0171 (8)	0.0199 (8)	0.0012 (6)	0.0084 (7)	0.0005 (6)
C5	0.0137 (8)	0.0121 (7)	0.0145 (8)	0.0007 (6)	0.0076 (6)	0.0004 (6)
C6	0.0159 (8)	0.0112 (7)	0.0122 (7)	−0.0010 (6)	0.0061 (6)	−0.0006 (6)
C7	0.0147 (8)	0.0191 (8)	0.0147 (8)	−0.0030 (6)	0.0044 (7)	−0.0020 (6)
C8	0.0120 (8)	0.0194 (8)	0.0177 (8)	0.0020 (6)	0.0043 (7)	−0.0005 (6)
C9	0.0153 (8)	0.0161 (8)	0.0160 (8)	0.0023 (6)	0.0073 (7)	0.0003 (6)
C10	0.0149 (8)	0.0108 (7)	0.0127 (8)	0.0005 (6)	0.0066 (6)	−0.0003 (6)

Geometric parameters (Å, º) top

O1W—H11	0.93 (3)	C2—H2A	0.9900
O1W—H12	0.92 (3)	C2—H2B	0.9900
O2W—H21	0.88 (3)	C3—C4	1.528 (2)
O2W—H22	0.86 (3)	C3—H3A	0.9900
N1—N2	1.4509 (19)	C3—H3B	0.9900
N1—C10	1.460 (2)	C4—C5	1.518 (2)
N1—H1	0.88 (2)	C4—H4A	0.9900
N2—C1	1.4748 (19)	C4—H4B	0.9900
N2—H2	0.91 (2)	C5—H5A	1.0000
N3—N6	1.4615 (17)	C6—C7	1.521 (2)
N3—C1	1.4715 (19)	C6—H6	1.0000
N3—C5	1.4853 (19)	C7—C8	1.528 (2)
N4—N5	1.4508 (19)	C7—H7A	0.9900
N4—C5	1.465 (2)	C7—H7B	0.9900
N4—H4	0.87 (2)	C8—C9	1.528 (2)
N5—C6	1.479 (2)	C8—H8A	0.9900
N5—H5	0.96 (2)	C8—H8B	0.9900
N6—C6	1.4633 (19)	C9—C10	1.519 (2)
N6—C10	1.4843 (19)	C9—H9A	0.9900
C1—C2	1.521 (2)	C9—H9B	0.9900
C1—H1A	1.0000	C10—H10A	1.0000
C2—C3	1.530 (2)

H11—O1W—H12	103 (2)	C3—C4—H4A	109.5
H21—O2W—H22	110 (2)	C5—C4—H4B	109.5
N2—N1—C10	113.12 (12)	C3—C4—H4B	109.5
N2—N1—H1	104.6 (12)	H4A—C4—H4B	108.1
C10—N1—H1	109.1 (13)	N4—C5—N3	109.28 (12)
N1—N2—C1	112.14 (12)	N4—C5—C4	109.79 (13)
N1—N2—H2	106.1 (12)	N3—C5—C4	109.95 (13)
C1—N2—H2	109.9 (13)	N4—C5—H5A	109.3
N6—N3—C1	107.21 (11)	N3—C5—H5A	109.3
N6—N3—C5	112.03 (11)	C4—C5—H5A	109.3
C1—N3—C5	115.01 (12)	N6—C6—N5	114.67 (12)
N5—N4—C5	112.67 (12)	N6—C6—C7	110.60 (13)
N5—N4—H4	107.5 (13)	N5—C6—C7	110.49 (13)
C5—N4—H4	108.6 (13)	N6—C6—H6	106.9
N4—N5—C6	111.18 (12)	N5—C6—H6	106.9
N4—N5—H5	106.0 (12)	C7—C6—H6	106.9
C6—N5—H5	110.3 (12)	C6—C7—C8	112.24 (13)
N3—N6—C6	107.29 (11)	C6—C7—H7A	109.2
N3—N6—C10	112.12 (11)	C8—C7—H7A	109.2
C6—N6—C10	114.95 (12)	C6—C7—H7B	109.2
N3—C1—N2	114.49 (12)	C8—C7—H7B	109.2
N3—C1—C2	109.88 (13)	H7A—C7—H7B	107.9
N2—C1—C2	110.24 (13)	C9—C8—C7	109.92 (13)
N3—C1—H1A	107.3	C9—C8—H8A	109.7
N2—C1—H1A	107.3	C7—C8—H8A	109.7
C2—C1—H1A	107.3	C9—C8—H8B	109.7
C1—C2—C3	112.22 (13)	C7—C8—H8B	109.7
C1—C2—H2A	109.2	H8A—C8—H8B	108.2
C3—C2—H2A	109.2	C10—C9—C8	111.07 (13)
C1—C2—H2B	109.2	C10—C9—H9A	109.4
C3—C2—H2B	109.2	C8—C9—H9A	109.4
H2A—C2—H2B	107.9	C10—C9—H9B	109.4
C4—C3—C2	109.67 (14)	C8—C9—H9B	109.4
C4—C3—H3A	109.7	H9A—C9—H9B	108.0
C2—C3—H3A	109.7	N1—C10—N6	110.36 (12)
C4—C3—H3B	109.7	N1—C10—C9	109.43 (13)
C2—C3—H3B	109.7	N6—C10—C9	108.58 (12)
H3A—C3—H3B	108.2	N1—C10—H10A	109.5
C5—C4—C3	110.60 (13)	N6—C10—H10A	109.5
C5—C4—H4A	109.5	C9—C10—H10A	109.5

C10—N1—N2—C1	−48.61 (17)	C1—N3—C5—C4	56.60 (16)
C5—N4—N5—C6	−50.99 (16)	C3—C4—C5—N4	−176.52 (13)
C1—N3—N6—C6	−174.01 (11)	C3—C4—C5—N3	−56.27 (17)
C5—N3—N6—C6	58.93 (14)	N3—N6—C6—N5	−55.08 (16)
C1—N3—N6—C10	58.87 (15)	C10—N6—C6—N5	70.36 (17)
C5—N3—N6—C10	−68.19 (15)	N3—N6—C6—C7	179.18 (12)
N6—N3—C1—N2	−55.16 (16)	C10—N6—C6—C7	−55.38 (17)
C5—N3—C1—N2	70.13 (17)	N4—N5—C6—N6	52.05 (17)
N6—N3—C1—C2	−179.84 (12)	N4—N5—C6—C7	177.85 (12)
C5—N3—C1—C2	−54.55 (16)	N6—C6—C7—C8	51.81 (18)
N1—N2—C1—N3	51.03 (17)	N5—C6—C7—C8	−76.24 (17)
N1—N2—C1—C2	175.52 (12)	C6—C7—C8—C9	−53.06 (18)
N3—C1—C2—C3	53.32 (17)	C7—C8—C9—C10	56.33 (18)
N2—C1—C2—C3	−73.78 (17)	N2—N1—C10—N6	52.49 (17)
C1—C2—C3—C4	−55.36 (17)	N2—N1—C10—C9	171.91 (12)
C2—C3—C4—C5	56.48 (17)	N3—N6—C10—N1	−59.00 (16)
N5—N4—C5—N3	55.05 (16)	C6—N6—C10—N1	178.11 (12)
N5—N4—C5—C4	175.72 (12)	N3—N6—C10—C9	−178.95 (11)
N6—N3—C5—N4	−60.10 (15)	C6—N6—C10—C9	58.17 (16)
C1—N3—C5—N4	177.16 (12)	C8—C9—C10—N1	−178.00 (13)
N6—N3—C5—C4	179.34 (12)	C8—C9—C10—N6	−57.48 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H11···N3ⁱ	0.93 (3)	1.99 (3)	2.922 (2)	174 (2)
O1W—H12···N5ⁱⁱ	0.92 (3)	2.05 (3)	2.960 (2)	178 (2)
O2W—H21···N2	0.88 (3)	2.05 (3)	2.925 (2)	172 (2)
O2W—H22···N4ⁱⁱ	0.86 (3)	2.02 (3)	2.863 (2)	167 (2)
N1—H1···O1W	0.88 (2)	2.08 (2)	2.964 (2)	175 (2)
N2—H2···O2Wⁱⁱⁱ	0.91 (2)	2.18 (2)	3.071 (2)	166 (2)
N4—H4···N5^iv	0.87 (2)	2.57 (2)	3.354 (2)	150.1 (15)
N5—H5···N1ⁱⁱⁱ	0.96 (2)	2.25 (2)	3.163 (2)	159 (2)

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

Experimental details

Crystal data
Chemical formula	C₁₀H₂₀N₆·2H₂O
M_r	260.35
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	9.5154 (10), 16.0667 (17), 9.1097 (10)
β (°)	114.916 (1)
V (Å³)	1263.1 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.20 × 0.20 × 0.05

Data collection
Diffractometer	Bruker SMART APEX
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	14226, 2896, 2138
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.116, 1.02
No. of reflections	2896
No. of parameters	195
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.23

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H11···N3ⁱ	0.93 (3)	1.99 (3)	2.922 (2)	174 (2)
O1W—H12···N5ⁱⁱ	0.92 (3)	2.05 (3)	2.960 (2)	178 (2)
O2W—H21···N2	0.88 (3)	2.05 (3)	2.925 (2)	172 (2)
O2W—H22···N4ⁱⁱ	0.86 (3)	2.02 (3)	2.863 (2)	167 (2)
N1—H1···O1W	0.88 (2)	2.08 (2)	2.964 (2)	175 (2)
N2—H2···O2Wⁱⁱⁱ	0.91 (2)	2.18 (2)	3.071 (2)	166 (2)
N4—H4···N5^iv	0.87 (2)	2.57 (2)	3.354 (2)	150.1 (15)
N5—H5···N1ⁱⁱⁱ	0.96 (2)	2.25 (2)	3.163 (2)	159 (2)

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

Acknowledgements

We thank the Ministry of Higher Education of Malaysia (grant No. UM.C/HIR/MOHE/SC/12) for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Katritzky, A. R. & Fan, W.-Q. (1990). J. Org. Chem. 55, 3205–3209. CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar