4-[(2-Benzoyl-4-chlorophenyl)diazenyl]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one

Bahreni, Z.; Rahmani, H.; Ng, S.W.

doi:10.1107/S1600536809004243

organic compounds

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ISSN: 2056-9890

Volume 65| Part 3| March 2009| Page o510

doi:10.1107/S1600536809004243

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4-[(2-Benzoyl-4-chlorophenyl)diazenyl]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one

Zaker Bahreni,^a Hossein Rahmani ^a and Seik Weng Ng ^b ^*

^aInstitute of Chemical Industries, Iranian Research Organization for Science and Technology, PO Box 15815-358, Tehran, Iran, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 3 February 2009; accepted 5 February 2009; online 11 February 2009)

In the title compound, C₂₃H₁₇ClN₄O₂, the amino H atom forms an intramolecular hydrogen bond to the exocyclic carbonyl O atom as well as to the O atom of the benzoyl group.

Related literature

For the crystal structure of 1-phenyl-3-methyl-4-(4′-chlorophenyazo)-pyrazol-5-one, whose amino H atom is intramolecularly hydrogen-bonded to the carbonyl O atom, see: Golinski et al. (1983 ).

Experimental

Crystal data

C₂₃H₁₇ClN₄O₂
M_r = 416.86
Monoclinic, C 2/c
a = 25.800 (3) Å
b = 12.124 (1) Å
c = 13.966 (1) Å
β = 119.179 (1)°
V = 3813.9 (7) Å³
Z = 8
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 120 (2) K
0.35 × 0.25 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.791, T_max = 0.862 (expected range = 0.897–0.977)
10753 measured reflections
4346 independent reflections
3309 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.105
S = 1.00
4346 reflections
276 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4⋯O1	0.89 (1)	2.06 (2)	2.755 (2)	135 (2)
N4—H4⋯O2	0.89 (1)	2.05 (2)	2.698 (2)	130 (2)

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); 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, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809004243/tk2371sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809004243/tk2371Isup2.hkl

checkCIF report

Related literature top

For the crystal structure of 1-phenyl-3-methyl-4-(-4'-chlorophenyazo)-pyrazol-5-one, whose amino H atom is intramolecularly hydrogen-bonded to the carbonyl O atom, see: Golinski et al. (1983).

Experimental top

2-Amino-5-chlorobenzophenone (2.32 g, 0.01 mol) was suspended in strong hydrochloric acid (20 ml, pH ca. 5) at 273 K. A solution of sodium nitrite (0.69 g in 15 ml water) was added. Following the diazotization, an aqueous solution of 3-methyl-1-phenyl-2-pyrazoline-5-one (1.75 g, 0.01 mol) was added. The compound that separated was collected and recrystallized from ethanol.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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, 2009).

Figures top

Fig. 1. Thermal displacement plot (Barbour, 2001) of C₂₃H₁₇ClN₄O₂; probability levels are set at 70% and H-atoms are drawn as spheres of arbitrary radius.

4-[(2-Benzoyl-4-chlorophenyl)diazenyl]-3-methyl-1-phenyl-1H-pyrazol- 5(4H)-one top

Crystal data top

C₂₃H₁₇ClN₄O₂	F(000) = 1728
M_r = 416.86	D_x = 1.452 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2643 reflections
a = 25.800 (3) Å	θ = 2.2–26.9°
b = 12.124 (1) Å	µ = 0.23 mm⁻¹
c = 13.966 (1) Å	T = 120 K
β = 119.179 (1)°	Block, orange
V = 3813.9 (7) Å³	0.35 × 0.25 × 0.10 mm
Z = 8

Data collection top

Bruker SMART APEX diffractometer	4346 independent reflections
Radiation source: fine-focus sealed tube	3309 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
ω scans	θ_max = 27.5°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −33→33
T_min = 0.791, T_max = 0.862	k = −15→12
10753 measured reflections	l = −18→17

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.05P)² + 2.1067P] where P = (F_o² + 2F_c²)/3
4346 reflections	(Δ/σ)_max = 0.001
276 parameters	Δρ_max = 0.30 e Å⁻³
1 restraint	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₂₃H₁₇ClN₄O₂	V = 3813.9 (7) Å³
M_r = 416.86	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 25.800 (3) Å	µ = 0.23 mm⁻¹
b = 12.124 (1) Å	T = 120 K
c = 13.966 (1) Å	0.35 × 0.25 × 0.10 mm
β = 119.179 (1)°

Data collection top

Bruker SMART APEX diffractometer	4346 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3309 reflections with I > 2σ(I)
T_min = 0.791, T_max = 0.862	R_int = 0.032
10753 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	1 restraint
wR(F²) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.30 e Å⁻³
4346 reflections	Δρ_min = −0.30 e Å⁻³
276 parameters

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

	x	y	z	U_iso*/U_eq
Cl1	0.176742 (18)	0.72052 (4)	0.10069 (4)	0.03104 (13)
O1	0.51920 (5)	0.65437 (10)	0.64529 (9)	0.0270 (3)
O2	0.42743 (6)	0.81878 (10)	0.49190 (10)	0.0301 (3)
N1	0.56804 (6)	0.48796 (11)	0.72365 (11)	0.0209 (3)
N2	0.55349 (6)	0.37433 (11)	0.70777 (11)	0.0208 (3)
N3	0.42128 (6)	0.49431 (11)	0.50462 (11)	0.0200 (3)
N4	0.40777 (6)	0.59936 (12)	0.47918 (11)	0.0204 (3)
H4	0.4336 (7)	0.6518 (13)	0.5167 (15)	0.037 (6)*
C1	0.62606 (7)	0.51899 (15)	0.80413 (13)	0.0214 (4)
C2	0.66295 (7)	0.44153 (15)	0.88027 (13)	0.0239 (4)
H2	0.6489	0.3691	0.8799	0.029*
C3	0.72042 (8)	0.47068 (16)	0.95664 (14)	0.0279 (4)
H3	0.7458	0.4175	1.0082	0.034*
C4	0.74136 (8)	0.57598 (16)	0.95878 (15)	0.0307 (4)
H4A	0.7810	0.5951	1.0108	0.037*
C5	0.70394 (8)	0.65311 (16)	0.88431 (15)	0.0310 (4)
H5	0.7179	0.7261	0.8866	0.037*
C6	0.64650 (8)	0.62588 (15)	0.80647 (14)	0.0270 (4)
H6	0.6213	0.6794	0.7552	0.032*
C7	0.52131 (7)	0.55349 (14)	0.65290 (13)	0.0204 (3)
C8	0.47428 (7)	0.47380 (14)	0.58702 (13)	0.0195 (3)
C9	0.49904 (7)	0.36666 (14)	0.62833 (13)	0.0201 (3)
C10	0.46871 (7)	0.25862 (14)	0.59029 (15)	0.0246 (4)
H10A	0.4962	0.1992	0.6323	0.037*
H10B	0.4559	0.2492	0.5122	0.037*
H10C	0.4340	0.2562	0.6012	0.037*
C11	0.35288 (7)	0.62787 (14)	0.38933 (13)	0.0198 (3)
C12	0.30754 (7)	0.55002 (14)	0.34178 (13)	0.0226 (4)
H12	0.3140	0.4770	0.3700	0.027*
C13	0.25322 (7)	0.57835 (15)	0.25382 (14)	0.0241 (4)
H13	0.2221	0.5255	0.2224	0.029*
C14	0.24456 (7)	0.68414 (15)	0.21197 (13)	0.0221 (4)
C15	0.28903 (7)	0.76156 (14)	0.25581 (13)	0.0213 (3)
H15	0.2822	0.8336	0.2252	0.026*
C16	0.34421 (7)	0.73499 (14)	0.34516 (13)	0.0200 (3)
C17	0.39169 (7)	0.82058 (14)	0.39359 (13)	0.0210 (3)
C18	0.39651 (7)	0.90830 (14)	0.32340 (13)	0.0205 (3)
C19	0.42522 (7)	1.00593 (14)	0.37423 (14)	0.0251 (4)
H19	0.4377	1.0172	0.4497	0.030*
C20	0.43574 (8)	1.08644 (15)	0.31600 (15)	0.0298 (4)
H20	0.4549	1.1531	0.3513	0.036*
C21	0.41840 (8)	1.07047 (15)	0.20623 (15)	0.0299 (4)
H21	0.4257	1.1259	0.1662	0.036*
C22	0.39037 (8)	0.97341 (15)	0.15512 (14)	0.0273 (4)
H22	0.3787	0.9623	0.0799	0.033*
C23	0.37924 (7)	0.89228 (14)	0.21274 (13)	0.0230 (4)
H23	0.3599	0.8259	0.1771	0.028*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0196 (2)	0.0284 (3)	0.0321 (2)	0.00060 (17)	0.00242 (17)	0.00243 (19)
O1	0.0295 (7)	0.0183 (7)	0.0261 (6)	−0.0014 (5)	0.0080 (5)	0.0012 (5)
O2	0.0339 (7)	0.0233 (7)	0.0217 (6)	−0.0045 (5)	0.0045 (5)	−0.0012 (5)
N1	0.0219 (7)	0.0173 (7)	0.0210 (7)	−0.0018 (6)	0.0086 (6)	0.0006 (5)
N2	0.0209 (7)	0.0177 (7)	0.0238 (7)	−0.0010 (6)	0.0109 (6)	0.0014 (6)
N3	0.0219 (7)	0.0200 (8)	0.0204 (7)	0.0008 (6)	0.0121 (6)	0.0028 (6)
N4	0.0210 (7)	0.0181 (8)	0.0195 (7)	−0.0015 (6)	0.0079 (6)	0.0013 (6)
C1	0.0192 (8)	0.0252 (9)	0.0193 (8)	−0.0022 (7)	0.0089 (7)	−0.0021 (7)
C2	0.0247 (9)	0.0248 (10)	0.0229 (8)	−0.0011 (7)	0.0121 (7)	−0.0003 (7)
C3	0.0263 (9)	0.0311 (10)	0.0233 (9)	0.0028 (8)	0.0097 (7)	0.0006 (8)
C4	0.0226 (9)	0.0373 (11)	0.0264 (9)	−0.0057 (8)	0.0073 (7)	−0.0078 (8)
C5	0.0309 (10)	0.0271 (10)	0.0325 (10)	−0.0085 (8)	0.0133 (8)	−0.0061 (8)
C6	0.0272 (9)	0.0239 (10)	0.0270 (9)	−0.0015 (7)	0.0109 (7)	0.0012 (7)
C7	0.0229 (8)	0.0209 (9)	0.0180 (8)	0.0010 (7)	0.0105 (7)	0.0024 (6)
C8	0.0209 (8)	0.0204 (9)	0.0184 (8)	−0.0010 (6)	0.0106 (7)	0.0017 (6)
C9	0.0193 (8)	0.0224 (9)	0.0205 (8)	0.0006 (7)	0.0111 (7)	0.0029 (7)
C10	0.0216 (8)	0.0198 (9)	0.0295 (9)	−0.0019 (7)	0.0102 (7)	−0.0006 (7)
C11	0.0184 (8)	0.0223 (9)	0.0185 (8)	0.0008 (6)	0.0090 (7)	−0.0007 (6)
C12	0.0245 (8)	0.0191 (9)	0.0251 (9)	−0.0001 (7)	0.0129 (7)	0.0036 (7)
C13	0.0211 (8)	0.0218 (9)	0.0276 (9)	−0.0047 (7)	0.0106 (7)	−0.0006 (7)
C14	0.0157 (8)	0.0261 (9)	0.0208 (8)	0.0021 (7)	0.0062 (6)	0.0000 (7)
C15	0.0214 (8)	0.0180 (9)	0.0233 (8)	0.0026 (6)	0.0100 (7)	0.0007 (7)
C16	0.0211 (8)	0.0193 (9)	0.0205 (8)	0.0003 (7)	0.0107 (7)	−0.0011 (6)
C17	0.0204 (8)	0.0178 (8)	0.0212 (8)	0.0024 (6)	0.0074 (7)	−0.0016 (7)
C18	0.0168 (7)	0.0180 (9)	0.0229 (8)	0.0016 (6)	0.0067 (6)	0.0008 (7)
C19	0.0231 (8)	0.0214 (9)	0.0248 (9)	−0.0009 (7)	0.0070 (7)	−0.0036 (7)
C20	0.0294 (9)	0.0188 (9)	0.0353 (10)	−0.0049 (7)	0.0110 (8)	−0.0018 (8)
C21	0.0300 (10)	0.0241 (10)	0.0348 (10)	−0.0013 (8)	0.0151 (8)	0.0053 (8)
C22	0.0266 (9)	0.0275 (10)	0.0247 (9)	0.0021 (7)	0.0099 (7)	0.0021 (7)
C23	0.0207 (8)	0.0192 (9)	0.0247 (9)	−0.0007 (7)	0.0076 (7)	−0.0019 (7)

Geometric parameters (Å, º) top

Cl1—C14	1.738 (2)	C10—H10A	0.9800
O1—C7	1.227 (2)	C10—H10B	0.9800
O2—C17	1.225 (2)	C10—H10C	0.9800
N1—C7	1.378 (2)	C11—C12	1.394 (2)
N1—C1	1.416 (2)	C11—C16	1.408 (2)
N1—N2	1.417 (2)	C12—C13	1.383 (2)
N2—C9	1.301 (2)	C12—H12	0.9500
N3—C8	1.312 (2)	C13—C14	1.382 (2)
N3—N4	1.323 (2)	C13—H13	0.9500
N4—C11	1.402 (2)	C14—C15	1.374 (2)
N4—H4	0.885 (9)	C15—C16	1.398 (2)
C1—C2	1.390 (2)	C15—H15	0.9500
C1—C6	1.393 (2)	C16—C17	1.492 (2)
C2—C3	1.385 (2)	C17—C18	1.492 (2)
C2—H2	0.9500	C18—C19	1.393 (2)
C3—C4	1.381 (3)	C18—C23	1.397 (2)
C3—H3	0.9500	C19—C20	1.380 (3)
C4—C5	1.382 (3)	C19—H19	0.9500
C4—H4A	0.9500	C20—C21	1.385 (3)
C5—C6	1.384 (3)	C20—H20	0.9500
C5—H5	0.9500	C21—C22	1.383 (3)
C6—H6	0.9500	C21—H21	0.9500
C7—C8	1.471 (2)	C22—C23	1.387 (2)
C8—C9	1.438 (2)	C22—H22	0.9500
C9—C10	1.485 (2)	C23—H23	0.9500

C7—N1—C1	129.3 (2)	H10B—C10—H10C	109.5
C7—N1—N2	112.1 (1)	C12—C11—N4	120.4 (2)
C1—N1—N2	118.7 (1)	C12—C11—C16	119.9 (2)
C9—N2—N1	107.2 (1)	N4—C11—C16	119.7 (1)
C8—N3—N4	116.3 (1)	C13—C12—C11	120.4 (2)
N3—N4—C11	119.8 (1)	C13—C12—H12	119.8
N3—N4—H4	121 (1)	C11—C12—H12	119.8
C11—N4—H4	120 (1)	C12—C13—C14	119.4 (2)
C2—C1—C6	120.0 (2)	C12—C13—H13	120.3
C2—C1—N1	119.5 (2)	C14—C13—H13	120.3
C6—C1—N1	120.5 (2)	C15—C14—C13	121.2 (2)
C3—C2—C1	119.6 (2)	C15—C14—Cl1	118.9 (1)
C3—C2—H2	120.2	C13—C14—Cl1	119.9 (1)
C1—C2—H2	120.2	C14—C15—C16	120.4 (2)
C4—C3—C2	120.9 (2)	C14—C15—H15	119.8
C4—C3—H3	119.6	C16—C15—H15	119.8
C2—C3—H3	119.6	C15—C16—C11	118.6 (2)
C3—C4—C5	119.2 (2)	C15—C16—C17	119.9 (2)
C3—C4—H4A	120.4	C11—C16—C17	121.5 (2)
C5—C4—H4A	120.4	O2—C17—C18	119.4 (2)
C4—C5—C6	121.2 (2)	O2—C17—C16	119.9 (2)
C4—C5—H5	119.4	C18—C17—C16	120.7 (1)
C6—C5—H5	119.4	C19—C18—C23	119.0 (2)
C5—C6—C1	119.2 (2)	C19—C18—C17	117.7 (2)
C5—C6—H6	120.4	C23—C18—C17	122.9 (2)
C1—C6—H6	120.4	C20—C19—C18	120.6 (2)
O1—C7—N1	128.6 (2)	C20—C19—H19	119.7
O1—C7—C8	127.8 (2)	C18—C19—H19	119.7
N1—C7—C8	103.7 (1)	C19—C20—C21	120.2 (2)
N3—C8—C9	126.3 (2)	C19—C20—H20	119.9
N3—C8—C7	127.8 (2)	C21—C20—H20	119.9
C9—C8—C7	105.8 (1)	C20—C21—C22	119.7 (2)
N2—C9—C8	111.2 (2)	C20—C21—H21	120.1
N2—C9—C10	122.0 (2)	C22—C21—H21	120.1
C8—C9—C10	126.8 (2)	C21—C22—C23	120.5 (2)
C9—C10—H10A	109.5	C21—C22—H22	119.7
C9—C10—H10B	109.5	C23—C22—H22	119.7
H10A—C10—H10B	109.5	C22—C23—C18	119.9 (2)
C9—C10—H10C	109.5	C22—C23—H23	120.0
H10A—C10—H10C	109.5	C18—C23—H23	120.0

C7—N1—N2—C9	0.5 (2)	N3—N4—C11—C12	14.3 (2)
C1—N1—N2—C9	−178.1 (1)	N3—N4—C11—C16	−164.0 (1)
C8—N3—N4—C11	177.4 (1)	N4—C11—C12—C13	179.4 (2)
C7—N1—C1—C2	168.3 (2)	C16—C11—C12—C13	−2.4 (2)
N2—N1—C1—C2	−13.4 (2)	C11—C12—C13—C14	1.2 (3)
C7—N1—C1—C6	−12.6 (3)	C12—C13—C14—C15	0.3 (3)
N2—N1—C1—C6	165.8 (2)	C12—C13—C14—Cl1	179.4 (1)
C6—C1—C2—C3	−1.4 (3)	C13—C14—C15—C16	−0.7 (3)
N1—C1—C2—C3	177.8 (2)	Cl1—C14—C15—C16	−179.8 (1)
C1—C2—C3—C4	0.6 (3)	C14—C15—C16—C11	−0.5 (2)
C2—C3—C4—C5	0.8 (3)	C14—C15—C16—C17	−178.6 (2)
C3—C4—C5—C6	−1.4 (3)	C12—C11—C16—C15	2.0 (2)
C4—C5—C6—C1	0.6 (3)	N4—C11—C16—C15	−179.8 (1)
C2—C1—C6—C5	0.8 (3)	C12—C11—C16—C17	−179.9 (2)
N1—C1—C6—C5	−178.4 (2)	N4—C11—C16—C17	−1.6 (2)
C1—N1—C7—O1	−1.6 (3)	C15—C16—C17—O2	148.1 (2)
N2—N1—C7—O1	180.0 (2)	C11—C16—C17—O2	−30.0 (2)
C1—N1—C7—C8	177.7 (2)	C15—C16—C17—C18	−32.3 (2)
N2—N1—C7—C8	−0.7 (2)	C11—C16—C17—C18	149.6 (2)
N4—N3—C8—C9	−179.0 (2)	O2—C17—C18—C19	−23.7 (2)
N4—N3—C8—C7	−1.8 (2)	C16—C17—C18—C19	156.7 (2)
O1—C7—C8—N3	2.3 (3)	O2—C17—C18—C23	149.5 (2)
N1—C7—C8—N3	−177.0 (2)	C16—C17—C18—C23	−30.1 (2)
O1—C7—C8—C9	180.0 (2)	C23—C18—C19—C20	0.9 (3)
N1—C7—C8—C9	0.6 (2)	C17—C18—C19—C20	174.4 (2)
N1—N2—C9—C8	−0.1 (2)	C18—C19—C20—C21	−0.7 (3)
N1—N2—C9—C10	−179.3 (1)	C19—C20—C21—C22	0.1 (3)
N3—C8—C9—N2	177.3 (2)	C20—C21—C22—C23	0.3 (3)
C7—C8—C9—N2	−0.4 (2)	C21—C22—C23—C18	−0.1 (3)
N3—C8—C9—C10	−3.5 (3)	C19—C18—C23—C22	−0.5 (2)
C7—C8—C9—C10	178.8 (2)	C17—C18—C23—C22	−173.6 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O1	0.89 (1)	2.06 (2)	2.755 (2)	135 (2)
N4—H4···O2	0.89 (1)	2.05 (2)	2.698 (2)	130 (2)

Experimental details

Crystal data
Chemical formula	C₂₃H₁₇ClN₄O₂
M_r	416.86
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	120
a, b, c (Å)	25.800 (3), 12.124 (1), 13.966 (1)
β (°)	119.179 (1)
V (Å³)	3813.9 (7)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.35 × 0.25 × 0.10

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.791, 0.862
No. of measured, independent and observed [I > 2σ(I)] reflections	10753, 4346, 3309
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.105, 1.00
No. of reflections	4346
No. of parameters	276
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.30

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O1	0.89 (1)	2.06 (2)	2.755 (2)	135 (2)
N4—H4···O2	0.89 (1)	2.05 (2)	2.698 (2)	130 (2)

Acknowledgements

We thank the Iranian Research Organization for Science and Technology and the University of Malaya for supporting this study.

References

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Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2009). publCIF. In preparation. Google Scholar