4-(3-Methyl-4,5-dihydro-1H-benzo[g]indazol-1-yl)benzene­sulfonamide

Asiri, A.M.; Faidallah, H.M.; Al-Youbi, A.O.; Makki, M.S.I.T.; Ng, S.W.

doi:10.1107/S1600536811033186

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2441

doi:10.1107/S1600536811033186

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4-(3-Methyl-4,5-dihydro-1H-benzo[g]indazol-1-yl)benzenesulfonamide

Abdullah M. Asiri,^a,^b Hassan M. Faidallah,^a Abdulrahman O. Al-Youbi,^a Mohamad S. I. T. Makki ^a and Seik Weng Ng ^c,^a ^*

^aChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia, ^bCenter of Excellence for Advanced Materials Research, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia, and ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 15 August 2011; accepted 16 August 2011; online 27 August 2011)

In the title compound, C₁₈H₁₇N₃O₂S, the aromatic ring bearing the sulfamide unit is aligned at 61.65 (1)° with respect to the pyrrole ring; its amino group forms N—H⋯N and N—H⋯O hydrogen bonds to neighboring molecules, generating sheets in the ac plane.

Related literature

For the crystal structure of a pyrrole synthesized using 2-acetyltetralone as a reactant, see: Portilla et al. (2007 ).

Experimental

Crystal data

C₁₈H₁₇N₃O₂S
M_r = 339.41
Monoclinic, P 2₁ /n
a = 4.8838 (1) Å
b = 27.3894 (4) Å
c = 12.2399 (2) Å
β = 94.738 (1)°
V = 1631.67 (5) Å³
Z = 4
Cu Kα radiation
μ = 1.89 mm⁻¹
T = 100 K
0.30 × 0.25 × 0.20 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ) T_min = 0.600, T_max = 0.703
11808 measured reflections
3255 independent reflections
3166 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.068
wR(F²) = 0.184
S = 1.11
3255 reflections
226 parameters
14 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.70 e Å⁻³
Δρ_min = −0.65 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N3ⁱ	0.88 (1)	2.05 (1)	2.925 (4)	173 (5)
N1—H2⋯O2ⁱⁱ	0.88 (1)	1.95 (2)	2.806 (4)	165 (4)
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) x-1, y, z.

Data collection: CrysAlis PRO (Agilent, 2010); 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: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811033186/bt5614sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811033186/bt5614Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811033186/bt5614Isup3.cml

checkCIF report

Comment top

Among the wide range of compounds tested for medicinal properties, the compounds having the benzenesulfonamide unit that is grafted to pyrazoles, a class of chemotherapeutically active heterocycles, are expected to exhibit enhanced activity. The ketone, 2-acetyl-tetralone, condenses with a variety of primary amines such as 5-amino-3-methyl-1H-pyrazole and 5-amino-3-tert-butyl-1H-pyrazole (Portilla et al., 2007). However, with 4-hydrazinobenzenesulfamide, the ketone yields a conventional Schiff base that cyclizes to form a pyrazole in a one-pot synthesis. In C₁₈H₁₇N₃O₂S (Scheme I), the benzene and pyrrole rings that are fused to a central cyclohexadiene ring are somewhat twisted owing to the –CH₂CH₂– fragment of the cyclohexadiene ring (dihedral angle between benzene and pyrrole rings is 17.3 (2) °. The benzene ring bearing the sulfamide unit is aligned at 61.6 (1) ° with respect to the pyrrole ring; its amino group is hydrogen-bond donor to the acceptor sites of neighboring molecules to generating sheets in the ac-plane (Table 1).

Related literature top

For the crystal structure of a pyrrole synthesized using 2-acetyltetralone as a reactant, see: Portilla et al. (2007).

Experimental top

2-Acetyl-1-tetralone (1.88 g, 10 mmol) in ethanol (50 ml) condensed with 4-hydrazinobenzenesulfonamide hydrochloride (2.2 g,10 mmol) by heating the reactants for 2 h. The mixture was allowed to cool, and the solid material was collected and recrystallized from ethanol.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); 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 C₁₈H₁₇N₃O₂S at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

4-(3-Methyl-4,5-dihydro-1H-benzo[g]indazol-1-yl)benzenesulfonamide top

Crystal data top

C₁₈H₁₇N₃O₂S	F(000) = 712
M_r = 339.41	D_x = 1.382 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2yn	Cell parameters from 7385 reflections
a = 4.8838 (1) Å	θ = 3.2–74.2°
b = 27.3894 (4) Å	µ = 1.89 mm⁻¹
c = 12.2399 (2) Å	T = 100 K
β = 94.738 (1)°	Prism, orange brown
V = 1631.67 (5) Å³	0.30 × 0.25 × 0.20 mm
Z = 4

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	3255 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	3166 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.018
Detector resolution: 10.4041 pixels mm^-1	θ_max = 74.4°, θ_min = 3.2°
ω scans	h = −3→6
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −34→33
T_min = 0.600, T_max = 0.703	l = −14→15
11808 measured reflections

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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.184	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ²(F_o²) + (0.0755P)² + 3.2939P] where P = (F_o² + 2F_c²)/3
3255 reflections	(Δ/σ)_max = 0.001
226 parameters	Δρ_max = 0.70 e Å⁻³
14 restraints	Δρ_min = −0.65 e Å⁻³

Crystal data top

C₁₈H₁₇N₃O₂S	V = 1631.67 (5) Å³
M_r = 339.41	Z = 4
Monoclinic, P2₁/n	Cu Kα radiation
a = 4.8838 (1) Å	µ = 1.89 mm⁻¹
b = 27.3894 (4) Å	T = 100 K
c = 12.2399 (2) Å	0.30 × 0.25 × 0.20 mm
β = 94.738 (1)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	3255 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	3166 reflections with I > 2σ(I)
T_min = 0.600, T_max = 0.703	R_int = 0.018
11808 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.068	14 restraints
wR(F²) = 0.184	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	Δρ_max = 0.70 e Å⁻³
3255 reflections	Δρ_min = −0.65 e Å⁻³
226 parameters

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

	x	y	z	U_iso*/U_eq
S1	0.89421 (18)	0.67458 (3)	0.78209 (7)	0.0424 (3)
O1	0.8478 (8)	0.63001 (10)	0.8387 (2)	0.0718 (11)
O2	1.1649 (6)	0.69481 (19)	0.7792 (3)	0.0936 (15)
N1	0.7213 (6)	0.71611 (10)	0.8343 (2)	0.0316 (6)
N2	0.4538 (6)	0.64587 (9)	0.3184 (2)	0.0325 (6)
N3	0.2861 (7)	0.68173 (10)	0.2717 (2)	0.0430 (8)
C1	0.4586 (7)	0.60588 (11)	0.2510 (2)	0.0286 (6)
C2	0.6045 (6)	0.55949 (10)	0.2675 (2)	0.0260 (6)
C3	0.8268 (6)	0.55121 (11)	0.3446 (2)	0.0287 (6)
H3	0.8945	0.5771	0.3909	0.034*
C4	0.9494 (7)	0.50567 (12)	0.3544 (2)	0.0338 (7)
H4	1.1012	0.5004	0.4068	0.041*
C5	0.8501 (7)	0.46774 (12)	0.2875 (3)	0.0348 (7)
H5	0.9295	0.4361	0.2957	0.042*
C6	0.6338 (7)	0.47599 (11)	0.2082 (2)	0.0305 (7)
H6	0.5698	0.4500	0.1616	0.037*
C7	0.5095 (6)	0.52151 (11)	0.1959 (2)	0.0260 (6)
C8	0.2724 (7)	0.53032 (12)	0.1096 (2)	0.0312 (7)
H8A	0.0975	0.5235	0.1423	0.037*
H8B	0.2875	0.5070	0.0486	0.037*
C9	0.2622 (8)	0.58217 (12)	0.0634 (2)	0.0373 (8)
H9A	0.4125	0.5870	0.0149	0.045*
H9B	0.0850	0.5878	0.0199	0.045*
C10	0.2932 (7)	0.61727 (12)	0.1578 (2)	0.0340 (7)
C11	0.1879 (8)	0.66404 (13)	0.1747 (3)	0.0407 (8)
C12	−0.0164 (11)	0.69262 (15)	0.1018 (4)	0.0586 (12)
H12A	−0.0683	0.7222	0.1399	0.088*
H12B	−0.1802	0.6726	0.0836	0.088*
H12C	0.0660	0.7016	0.0343	0.088*
C13	0.5657 (7)	0.65231 (11)	0.4290 (2)	0.0293 (7)
C14	0.7437 (8)	0.69042 (14)	0.4540 (3)	0.0435 (9)
H14	0.7941	0.7118	0.3979	0.052*
C15	0.8491 (8)	0.69741 (14)	0.5616 (3)	0.0462 (9)
H15	0.9728	0.7235	0.5798	0.055*
C16	0.7714 (7)	0.66571 (12)	0.6426 (3)	0.0316 (7)
C17	0.5945 (7)	0.62796 (12)	0.6171 (3)	0.0344 (7)
H17	0.5436	0.6065	0.6729	0.041*
C18	0.4900 (7)	0.62110 (12)	0.5098 (3)	0.0333 (7)
H18	0.3664	0.5950	0.4917	0.040*
H1	0.756 (10)	0.7464 (7)	0.815 (4)	0.061 (14)*
H2	0.547 (3)	0.7076 (14)	0.829 (3)	0.041 (11)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0376 (5)	0.0539 (6)	0.0321 (5)	0.0161 (4)	−0.0181 (3)	−0.0213 (4)
O1	0.134 (3)	0.0376 (14)	0.0361 (14)	0.0337 (17)	−0.0418 (17)	−0.0086 (11)
O2	0.0354 (16)	0.172 (4)	0.072 (2)	0.001 (2)	−0.0045 (15)	−0.070 (3)
N1	0.0401 (16)	0.0257 (13)	0.0280 (13)	−0.0022 (11)	−0.0041 (11)	−0.0051 (10)
N2	0.0532 (17)	0.0240 (12)	0.0185 (12)	0.0055 (11)	−0.0070 (11)	0.0000 (9)
N3	0.069 (2)	0.0290 (14)	0.0290 (15)	0.0111 (14)	−0.0105 (14)	0.0018 (11)
C1	0.0418 (17)	0.0252 (14)	0.0182 (13)	−0.0001 (12)	−0.0021 (12)	0.0003 (11)
C2	0.0346 (16)	0.0257 (14)	0.0173 (13)	−0.0009 (12)	−0.0006 (11)	−0.0018 (11)
C3	0.0326 (16)	0.0316 (15)	0.0210 (14)	0.0013 (12)	−0.0039 (11)	−0.0035 (11)
C4	0.0394 (18)	0.0405 (17)	0.0208 (14)	0.0080 (14)	−0.0018 (12)	−0.0006 (12)
C5	0.0451 (19)	0.0299 (15)	0.0296 (16)	0.0081 (14)	0.0041 (14)	0.0006 (12)
C6	0.0451 (18)	0.0264 (14)	0.0203 (14)	−0.0047 (13)	0.0041 (12)	−0.0035 (11)
C7	0.0313 (15)	0.0293 (14)	0.0175 (13)	−0.0038 (12)	0.0024 (11)	−0.0023 (11)
C8	0.0371 (17)	0.0366 (16)	0.0189 (14)	−0.0040 (13)	−0.0039 (12)	−0.0048 (12)
C9	0.051 (2)	0.0397 (18)	0.0191 (14)	0.0002 (15)	−0.0066 (13)	−0.0019 (13)
C10	0.0474 (19)	0.0321 (16)	0.0211 (14)	−0.0003 (14)	−0.0058 (13)	0.0024 (12)
C11	0.059 (2)	0.0350 (17)	0.0256 (16)	0.0056 (16)	−0.0105 (15)	0.0034 (13)
C12	0.083 (3)	0.043 (2)	0.044 (2)	0.016 (2)	−0.026 (2)	0.0050 (17)
C13	0.0408 (17)	0.0245 (14)	0.0211 (14)	0.0039 (12)	−0.0056 (12)	−0.0041 (11)
C14	0.057 (2)	0.0407 (19)	0.0329 (18)	−0.0142 (17)	0.0063 (16)	−0.0043 (15)
C15	0.046 (2)	0.049 (2)	0.044 (2)	−0.0169 (17)	0.0021 (16)	−0.0193 (17)
C16	0.0301 (16)	0.0381 (16)	0.0248 (15)	0.0071 (13)	−0.0074 (12)	−0.0104 (12)
C17	0.0456 (19)	0.0330 (16)	0.0227 (15)	0.0008 (14)	−0.0085 (13)	−0.0001 (12)
C18	0.0418 (18)	0.0312 (15)	0.0247 (15)	−0.0050 (13)	−0.0098 (13)	−0.0008 (12)

Geometric parameters (Å, º) top

S1—O1	1.431 (3)	C7—C8	1.521 (4)
S1—O2	1.437 (4)	C8—C9	1.528 (5)
S1—N1	1.582 (3)	C8—H8A	0.9900
S1—C16	1.778 (3)	C8—H8B	0.9900
N1—H1	0.882 (11)	C9—C10	1.502 (4)
N1—H2	0.880 (11)	C9—H9A	0.9900
N2—N3	1.373 (4)	C9—H9B	0.9900
N2—C1	1.372 (4)	C10—C11	1.402 (5)
N2—C13	1.428 (4)	C11—C12	1.503 (5)
N3—C11	1.334 (5)	C12—H12A	0.9800
C1—C10	1.377 (4)	C12—H12B	0.9800
C1—C2	1.463 (4)	C12—H12C	0.9800
C2—C7	1.413 (4)	C13—C14	1.377 (5)
C2—C3	1.398 (4)	C13—C18	1.381 (4)
C3—C4	1.385 (4)	C14—C15	1.387 (5)
C3—H3	0.9500	C14—H14	0.9500
C4—C5	1.385 (5)	C15—C16	1.395 (5)
C4—H4	0.9500	C15—H15	0.9500
C5—C6	1.392 (5)	C16—C17	1.367 (5)
C5—H5	0.9500	C17—C18	1.382 (4)
C6—C7	1.390 (4)	C17—H17	0.9500
C6—H6	0.9500	C18—H18	0.9500

O1—S1—O2	121.6 (3)	C9—C8—H8B	108.8
O1—S1—N1	107.85 (18)	H8A—C8—H8B	107.7
O2—S1—N1	104.8 (2)	C10—C9—C8	108.2 (2)
O1—S1—C16	107.07 (16)	C10—C9—H9A	110.1
O2—S1—C16	105.50 (19)	C8—C9—H9A	110.1
N1—S1—C16	109.67 (15)	C10—C9—H9B	110.1
S1—N1—H1	116 (3)	C8—C9—H9B	110.1
S1—N1—H2	109 (3)	H9A—C9—H9B	108.4
H1—N1—H2	116 (4)	C1—C10—C11	106.4 (3)
N3—N2—C1	111.1 (2)	C1—C10—C9	120.5 (3)
N3—N2—C13	118.3 (2)	C11—C10—C9	133.1 (3)
C1—N2—C13	130.1 (3)	N3—C11—C10	110.7 (3)
C11—N3—N2	105.6 (3)	N3—C11—C12	120.8 (3)
N2—C1—C10	106.2 (3)	C10—C11—C12	128.5 (3)
N2—C1—C2	130.0 (3)	C11—C12—H12A	109.5
C10—C1—C2	123.8 (3)	C11—C12—H12B	109.5
C7—C2—C3	119.8 (3)	H12A—C12—H12B	109.5
C7—C2—C1	115.0 (3)	C11—C12—H12C	109.5
C3—C2—C1	125.2 (3)	H12A—C12—H12C	109.5
C4—C3—C2	120.7 (3)	H12B—C12—H12C	109.5
C4—C3—H3	119.6	C14—C13—C18	120.8 (3)
C2—C3—H3	119.6	C14—C13—N2	119.3 (3)
C5—C4—C3	119.8 (3)	C18—C13—N2	119.9 (3)
C5—C4—H4	120.1	C13—C14—C15	119.6 (3)
C3—C4—H4	120.1	C13—C14—H14	120.2
C4—C5—C6	119.9 (3)	C15—C14—H14	120.2
C4—C5—H5	120.1	C14—C15—C16	119.2 (3)
C6—C5—H5	120.1	C14—C15—H15	120.4
C7—C6—C5	121.4 (3)	C16—C15—H15	120.4
C7—C6—H6	119.3	C17—C16—C15	120.8 (3)
C5—C6—H6	119.3	C17—C16—S1	118.7 (3)
C6—C7—C2	118.4 (3)	C15—C16—S1	120.5 (3)
C6—C7—C8	121.2 (3)	C16—C17—C18	119.8 (3)
C2—C7—C8	120.4 (3)	C16—C17—H17	120.1
C7—C8—C9	113.8 (3)	C18—C17—H17	120.1
C7—C8—H8A	108.8	C17—C18—C13	119.8 (3)
C9—C8—H8A	108.8	C17—C18—H18	120.1
C7—C8—H8B	108.8	C13—C18—H18	120.1

C1—N2—N3—C11	−0.4 (4)	C8—C9—C10—C1	34.6 (4)
C13—N2—N3—C11	−173.2 (3)	C8—C9—C10—C11	−147.1 (4)
N3—N2—C1—C10	1.3 (4)	N2—N3—C11—C10	−0.7 (4)
C13—N2—C1—C10	173.0 (3)	N2—N3—C11—C12	177.0 (4)
N3—N2—C1—C2	−179.2 (3)	C1—C10—C11—N3	1.5 (4)
C13—N2—C1—C2	−7.5 (6)	C9—C10—C11—N3	−177.0 (4)
N2—C1—C2—C7	163.9 (3)	C1—C10—C11—C12	−176.0 (4)
C10—C1—C2—C7	−16.6 (5)	C9—C10—C11—C12	5.5 (7)
N2—C1—C2—C3	−17.6 (5)	N3—N2—C13—C14	−63.9 (5)
C10—C1—C2—C3	161.8 (3)	C1—N2—C13—C14	124.9 (4)
C7—C2—C3—C4	−2.2 (5)	N3—N2—C13—C18	114.7 (4)
C1—C2—C3—C4	179.4 (3)	C1—N2—C13—C18	−56.5 (5)
C2—C3—C4—C5	−0.4 (5)	C18—C13—C14—C15	0.2 (6)
C3—C4—C5—C6	2.2 (5)	N2—C13—C14—C15	178.8 (3)
C4—C5—C6—C7	−1.5 (5)	C13—C14—C15—C16	−0.3 (6)
C5—C6—C7—C2	−1.1 (5)	C14—C15—C16—C17	0.3 (6)
C5—C6—C7—C8	−179.7 (3)	C14—C15—C16—S1	−178.1 (3)
C3—C2—C7—C6	2.9 (4)	O1—S1—C16—C17	18.0 (3)
C1—C2—C7—C6	−178.5 (3)	O2—S1—C16—C17	148.8 (3)
C3—C2—C7—C8	−178.5 (3)	N1—S1—C16—C17	−98.8 (3)
C1—C2—C7—C8	0.1 (4)	O1—S1—C16—C15	−163.6 (3)
C6—C7—C8—C9	−148.2 (3)	O2—S1—C16—C15	−32.7 (4)
C2—C7—C8—C9	33.2 (4)	N1—S1—C16—C15	79.7 (3)
C7—C8—C9—C10	−48.0 (4)	C15—C16—C17—C18	−0.3 (5)
N2—C1—C10—C11	−1.6 (4)	S1—C16—C17—C18	178.2 (3)
C2—C1—C10—C11	178.8 (3)	C16—C17—C18—C13	0.2 (5)
N2—C1—C10—C9	177.1 (3)	C14—C13—C18—C17	−0.2 (5)
C2—C1—C10—C9	−2.5 (5)	N2—C13—C18—C17	−178.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N3ⁱ	0.88 (1)	2.05 (1)	2.925 (4)	173 (5)
N1—H2···O2ⁱⁱ	0.88 (1)	1.95 (2)	2.806 (4)	165 (4)

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₇N₃O₂S
M_r	339.41
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	4.8838 (1), 27.3894 (4), 12.2399 (2)
β (°)	94.738 (1)
V (Å³)	1631.67 (5)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	1.89
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.600, 0.703
No. of measured, independent and observed [I > 2σ(I)] reflections	11808, 3255, 3166
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.068, 0.184, 1.11
No. of reflections	3255
No. of parameters	226
No. of restraints	14
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.70, −0.65

Computer programs: CrysAlis PRO (Agilent, 2010), 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
N1—H1···N3ⁱ	0.88 (1)	2.05 (1)	2.925 (4)	173 (5)
N1—H2···O2ⁱⁱ	0.88 (1)	1.95 (2)	2.806 (4)	165 (4)

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

Acknowledgements

We thank King Abdulaziz University and the University of Malaya for supporting this study.

References

Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Portilla, J., Quiroga, J., Cobo, J., Low, J. N. & Glidewell, C. (2007). Acta Cryst. C63, o458–o461. CrossRef IUCr Journals 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