4-(Dimethyl­amino)­pyridinium tetra­chlorido(quinoline-2-carboxyl­ato-κ2N,O)stannate(IV)

Najafi, E.; Amini, M.M.; Ng, S.W.

doi:10.1107/S1600536811031473

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page m1224

doi:10.1107/S1600536811031473

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4-(Dimethylamino)pyridinium tetrachlorido(quinoline-2-carboxylato-κ²N,O)stannate(IV)

Ezzatollah Najafi,^a Mostafa M. Amini ^a and Seik Weng Ng ^b,^c ^*

^aDepartment of Chemistry, General Campus, Shahid Beheshti University, Tehran 1983963113, Iran, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 1 August 2011; accepted 4 August 2011; online 11 August 2011)

In the title salt, (C₇H₁₁N₂)[SnCl₄(C₁₀H₆NO₂)], the Sn^IV atom is chelated by the N,O-bidentate carboxylate ions and four chloride ions, showing a distorted octahedral SnNOCl₄ coordination. In the crystal, the cation and anion are linked by a pyridinium–carboxylate N—H⋯O hydrogen bond.

Related literature

For a related ammonium tetrachlorido(pyridine-2-carboxylato)stannate(IV), see: Najafi et al. (2011 ).

Experimental

Crystal data

(C₇H₁₁N₂)[SnCl₄(C₁₀H₆NO₂)]
M_r = 555.83
Triclinic, $[P \overline 1]$
a = 8.6681 (3) Å
b = 8.8407 (4) Å
c = 14.4447 (5) Å
α = 96.721 (3)°
β = 91.924 (3)°
γ = 108.038 (4)°
V = 1042.43 (7) Å³
Z = 2
Mo Kα radiation
μ = 1.76 mm⁻¹
T = 100 K
0.30 × 0.20 × 0.10 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ) T_min = 0.621, T_max = 0.844
8056 measured reflections
4610 independent reflections
4202 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.021
wR(F²) = 0.047
S = 1.06
4610 reflections
250 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.52 e Å⁻³
Δρ_min = −0.49 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O1	0.87 (1)	1.98 (1)	2.816 (2)	160 (2)

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/S1600536811031473/xu5284sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811031473/xu5284Isup2.hkl

checkCIF report

Comment top

We have recently synthesized some ammonium tetrachlorido(carboxylato)stannates; in a recent study, we reacted stannic chloride with pyridine-2-carboxylic acid and triethylamine to yield the chelated stannate salt (Najafi et al., 2011). The use of quinoline-2-carboxylic acid and 4-dimethyaminopyridine yielded the expected dimethylaminopyridinium stannate in which the amine is protonated on the aromatic nitrogen atom (Scheme I, Fig. 1). The Sn^IV atom is chelated by the N,O-bidentate carboxylate ligand and four chloride ions, and shows octahedral SnNOCl₄ coordination at the metal atom. The cation and anion are linked an N–H_pyridinium···O hydrogen bond (Table 1).

Related literature top

For a related ammonium tetrachlorido(pyridine-2-carboxylato)stannate(IV), see: Najafi et al. (2011).

Experimental top

Stannic chloride pentahydrate (1 mmol), quinoline-2-carboxylic acid (1 mmol) and 4-dimethylaminopyridine (1 mmol) were loaded into a convection tube and the tube was filled with dry methanol and kept at 333 K. Colorless crystals were collected from the side arm after several days.

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. Thermal ellipsoid plot (Barbour, 2001) of (C₇H₁₁N₂)[SnCl₄(C₁₀H₆NO₂)] at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

4-(Dimethylamino)pyridinium tetrachlorido(quinoline-2-carboxylato-κ²N,O)stannate(IV) top

Crystal data top

(C₇H₁₁N₂)[SnCl₄(C₁₀H₆NO₂)]	Z = 2
M_r = 555.83	F(000) = 548
Triclinic, P1	D_x = 1.771 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.6681 (3) Å	Cell parameters from 5833 reflections
b = 8.8407 (4) Å	θ = 2.4–29.2°
c = 14.4447 (5) Å	µ = 1.76 mm⁻¹
α = 96.721 (3)°	T = 100 K
β = 91.924 (3)°	Block, colorless
γ = 108.038 (4)°	0.30 × 0.20 × 0.10 mm
V = 1042.43 (7) Å³

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	4610 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	4202 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.022
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.5°, θ_min = 2.5°
ω scans	h = −8→11
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −11→11
T_min = 0.621, T_max = 0.844	l = −18→18
8056 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)] = 0.021	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.047	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0181P)² + 0.127P] where P = (F_o² + 2F_c²)/3
4610 reflections	(Δ/σ)_max = 0.001
250 parameters	Δρ_max = 0.52 e Å⁻³
1 restraint	Δρ_min = −0.49 e Å⁻³

Crystal data top

(C₇H₁₁N₂)[SnCl₄(C₁₀H₆NO₂)]	γ = 108.038 (4)°
M_r = 555.83	V = 1042.43 (7) Å³
Triclinic, P1	Z = 2
a = 8.6681 (3) Å	Mo Kα radiation
b = 8.8407 (4) Å	µ = 1.76 mm⁻¹
c = 14.4447 (5) Å	T = 100 K
α = 96.721 (3)°	0.30 × 0.20 × 0.10 mm
β = 91.924 (3)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	4610 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	4202 reflections with I > 2σ(I)
T_min = 0.621, T_max = 0.844	R_int = 0.022
8056 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.021	1 restraint
wR(F²) = 0.047	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.52 e Å⁻³
4610 reflections	Δρ_min = −0.49 e Å⁻³
250 parameters

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

	x	y	z	U_iso*/U_eq
Sn1	0.361135 (16)	0.258730 (15)	0.271428 (9)	0.01232 (5)
Cl1	0.16903 (6)	0.37830 (6)	0.33361 (4)	0.02211 (12)
Cl2	0.13953 (6)	0.04597 (6)	0.18599 (3)	0.01824 (11)
Cl3	0.41373 (6)	0.41174 (6)	0.14341 (4)	0.02133 (11)
Cl4	0.58090 (6)	0.44245 (6)	0.37084 (4)	0.02246 (12)
O1	0.51697 (17)	0.14313 (16)	0.21142 (9)	0.0165 (3)
O2	0.57573 (18)	−0.08559 (17)	0.19327 (10)	0.0207 (3)
N1	0.36250 (19)	0.06808 (18)	0.36458 (10)	0.0124 (3)
N2	1.0685 (2)	0.3405 (2)	−0.12106 (11)	0.0173 (4)
N3	0.7058 (2)	0.2281 (2)	0.05939 (12)	0.0203 (4)
H3	0.629 (2)	0.206 (3)	0.0979 (13)	0.024 (6)*
C1	0.2921 (2)	0.0400 (2)	0.44784 (13)	0.0134 (4)
C2	0.2404 (2)	0.1582 (2)	0.49972 (13)	0.0173 (4)
H2	0.2535	0.2582	0.4777	0.021*
C3	0.1712 (3)	0.1279 (3)	0.58221 (14)	0.0203 (5)
H3A	0.1369	0.2080	0.6172	0.024*
C4	0.1499 (3)	−0.0194 (3)	0.61614 (14)	0.0219 (5)
H4	0.0987	−0.0389	0.6726	0.026*
C5	0.2022 (2)	−0.1341 (3)	0.56843 (14)	0.0194 (5)
H5	0.1888	−0.2327	0.5923	0.023*
C6	0.2768 (2)	−0.1071 (2)	0.48305 (13)	0.0158 (4)
C7	0.3379 (2)	−0.2201 (2)	0.43302 (14)	0.0172 (4)
H7	0.3269	−0.3199	0.4550	0.021*
C8	0.4130 (2)	−0.1860 (2)	0.35297 (13)	0.0164 (4)
H8	0.4577	−0.2598	0.3196	0.020*
C9	0.4230 (2)	−0.0400 (2)	0.32101 (13)	0.0133 (4)
C10	0.5114 (2)	0.0037 (2)	0.23433 (13)	0.0145 (4)
C11	0.9504 (2)	0.3054 (2)	−0.06169 (13)	0.0143 (4)
C12	0.9714 (3)	0.2416 (2)	0.02178 (14)	0.0184 (4)
H12	1.0717	0.2248	0.0375	0.022*
C13	0.8486 (3)	0.2047 (2)	0.07897 (14)	0.0205 (5)
H13	0.8638	0.1612	0.1344	0.025*
C14	0.6811 (3)	0.2898 (2)	−0.01880 (14)	0.0199 (5)
H14	0.5797	0.3062	−0.0316	0.024*
C15	0.7983 (2)	0.3288 (2)	−0.07943 (14)	0.0166 (4)
H15	0.7784	0.3720	−0.1341	0.020*
C16	1.2127 (3)	0.2906 (3)	−0.10898 (16)	0.0242 (5)
H16A	1.2761	0.3488	−0.0511	0.036*
H16B	1.2794	0.3146	−0.1621	0.036*
H16C	1.1793	0.1750	−0.1057	0.036*
C17	1.0413 (3)	0.3978 (3)	−0.20898 (14)	0.0258 (5)
H17A	0.9928	0.4840	−0.1971	0.039*
H17B	0.9676	0.3091	−0.2522	0.039*
H17C	1.1454	0.4388	−0.2367	0.039*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.01240 (7)	0.01035 (8)	0.01461 (8)	0.00357 (6)	0.00258 (5)	0.00280 (5)
Cl1	0.0238 (3)	0.0179 (3)	0.0275 (3)	0.0104 (2)	0.0071 (2)	0.0023 (2)
Cl2	0.0183 (3)	0.0146 (2)	0.0197 (2)	0.0034 (2)	−0.0038 (2)	0.00033 (19)
Cl3	0.0229 (3)	0.0214 (3)	0.0235 (3)	0.0086 (2)	0.0061 (2)	0.0125 (2)
Cl4	0.0208 (3)	0.0168 (3)	0.0243 (3)	−0.0010 (2)	−0.0032 (2)	0.0012 (2)
O1	0.0185 (7)	0.0168 (7)	0.0173 (7)	0.0084 (6)	0.0074 (6)	0.0045 (6)
O2	0.0244 (8)	0.0229 (8)	0.0197 (8)	0.0145 (7)	0.0054 (6)	0.0025 (6)
N1	0.0110 (8)	0.0117 (8)	0.0134 (8)	0.0021 (7)	0.0000 (7)	0.0015 (6)
N2	0.0155 (9)	0.0163 (9)	0.0181 (9)	0.0026 (7)	0.0042 (7)	0.0005 (7)
N3	0.0200 (10)	0.0245 (10)	0.0175 (9)	0.0072 (8)	0.0089 (8)	0.0042 (7)
C1	0.0110 (9)	0.0149 (10)	0.0122 (9)	0.0010 (8)	−0.0007 (8)	0.0027 (8)
C2	0.0167 (10)	0.0170 (11)	0.0171 (10)	0.0039 (9)	−0.0004 (8)	0.0024 (8)
C3	0.0164 (11)	0.0256 (12)	0.0177 (10)	0.0062 (9)	0.0013 (9)	−0.0013 (9)
C4	0.0159 (11)	0.0329 (13)	0.0134 (10)	0.0027 (10)	0.0022 (8)	0.0030 (9)
C5	0.0159 (10)	0.0194 (11)	0.0183 (10)	−0.0027 (9)	−0.0010 (9)	0.0075 (9)
C6	0.0126 (10)	0.0164 (10)	0.0155 (10)	0.0006 (8)	−0.0029 (8)	0.0032 (8)
C7	0.0187 (11)	0.0117 (10)	0.0187 (10)	0.0012 (9)	−0.0048 (9)	0.0034 (8)
C8	0.0166 (10)	0.0146 (10)	0.0169 (10)	0.0052 (9)	−0.0034 (8)	−0.0013 (8)
C9	0.0113 (9)	0.0139 (10)	0.0136 (10)	0.0033 (8)	−0.0012 (8)	0.0003 (8)
C10	0.0120 (10)	0.0171 (10)	0.0136 (10)	0.0039 (8)	−0.0016 (8)	0.0019 (8)
C11	0.0157 (10)	0.0098 (9)	0.0154 (10)	0.0021 (8)	0.0023 (8)	−0.0022 (7)
C12	0.0170 (10)	0.0204 (11)	0.0193 (10)	0.0084 (9)	0.0006 (9)	0.0020 (8)
C13	0.0245 (12)	0.0204 (11)	0.0179 (10)	0.0077 (10)	0.0017 (9)	0.0062 (8)
C14	0.0178 (11)	0.0230 (12)	0.0198 (11)	0.0096 (9)	0.0000 (9)	−0.0020 (9)
C15	0.0195 (11)	0.0174 (10)	0.0143 (10)	0.0086 (9)	−0.0002 (8)	0.0002 (8)
C16	0.0132 (10)	0.0261 (12)	0.0317 (12)	0.0054 (9)	0.0070 (9)	−0.0015 (10)
C17	0.0333 (13)	0.0236 (12)	0.0204 (11)	0.0065 (10)	0.0118 (10)	0.0068 (9)

Geometric parameters (Å, º) top

Sn1—O1	2.0848 (13)	C4—H4	0.9500
Sn1—N1	2.2790 (16)	C5—C6	1.422 (3)
Sn1—Cl1	2.3802 (5)	C5—H5	0.9500
Sn1—Cl4	2.3840 (5)	C6—C7	1.409 (3)
Sn1—Cl3	2.3912 (5)	C7—C8	1.365 (3)
Sn1—Cl2	2.4106 (5)	C7—H7	0.9500
O1—C10	1.301 (2)	C8—C9	1.400 (3)
O2—C10	1.213 (2)	C8—H8	0.9500
N1—C9	1.333 (2)	C9—C10	1.516 (3)
N1—C1	1.381 (2)	C11—C15	1.416 (3)
N2—C11	1.343 (2)	C11—C12	1.419 (3)
N2—C17	1.459 (3)	C12—C13	1.353 (3)
N2—C16	1.460 (3)	C12—H12	0.9500
N3—C13	1.343 (3)	C13—H13	0.9500
N3—C14	1.348 (3)	C14—C15	1.353 (3)
N3—H3	0.869 (9)	C14—H14	0.9500
C1—C2	1.408 (3)	C15—H15	0.9500
C1—C6	1.421 (3)	C16—H16A	0.9800
C2—C3	1.369 (3)	C16—H16B	0.9800
C2—H2	0.9500	C16—H16C	0.9800
C3—C4	1.406 (3)	C17—H17A	0.9800
C3—H3A	0.9500	C17—H17B	0.9800
C4—C5	1.360 (3)	C17—H17C	0.9800

O1—Sn1—N1	75.24 (5)	C7—C6—C5	122.27 (19)
O1—Sn1—Cl1	176.27 (4)	C1—C6—C5	118.72 (19)
N1—Sn1—Cl1	104.74 (4)	C8—C7—C6	119.87 (18)
O1—Sn1—Cl4	90.93 (4)	C8—C7—H7	120.1
N1—Sn1—Cl4	88.46 (4)	C6—C7—H7	120.1
Cl1—Sn1—Cl4	92.797 (19)	C7—C8—C9	118.64 (19)
O1—Sn1—Cl3	85.08 (4)	C7—C8—H8	120.7
N1—Sn1—Cl3	160.21 (4)	C9—C8—H8	120.7
Cl1—Sn1—Cl3	94.762 (18)	N1—C9—C8	123.44 (17)
Cl4—Sn1—Cl3	93.991 (19)	N1—C9—C10	116.83 (17)
O1—Sn1—Cl2	87.29 (4)	C8—C9—C10	119.70 (17)
N1—Sn1—Cl2	83.40 (4)	O2—C10—O1	124.30 (18)
Cl1—Sn1—Cl2	89.002 (18)	O2—C10—C9	120.59 (18)
Cl4—Sn1—Cl2	171.852 (17)	O1—C10—C9	115.05 (17)
Cl3—Sn1—Cl2	93.779 (18)	N2—C11—C15	121.88 (18)
C10—O1—Sn1	118.81 (12)	N2—C11—C12	121.52 (19)
C9—N1—C1	119.22 (16)	C15—C11—C12	116.60 (18)
C9—N1—Sn1	110.22 (12)	C13—C12—C11	119.88 (19)
C1—N1—Sn1	129.82 (13)	C13—C12—H12	120.1
C11—N2—C17	120.69 (18)	C11—C12—H12	120.1
C11—N2—C16	120.42 (17)	N3—C13—C12	121.67 (19)
C17—N2—C16	117.65 (17)	N3—C13—H13	119.2
C13—N3—C14	120.35 (18)	C12—C13—H13	119.2
C13—N3—H3	120.3 (15)	N3—C14—C15	121.2 (2)
C14—N3—H3	119.4 (15)	N3—C14—H14	119.4
N1—C1—C2	120.50 (17)	C15—C14—H14	119.4
N1—C1—C6	119.72 (17)	C14—C15—C11	120.29 (19)
C2—C1—C6	119.74 (17)	C14—C15—H15	119.9
C3—C2—C1	119.50 (19)	C11—C15—H15	119.9
C3—C2—H2	120.2	N2—C16—H16A	109.5
C1—C2—H2	120.2	N2—C16—H16B	109.5
C2—C3—C4	121.3 (2)	H16A—C16—H16B	109.5
C2—C3—H3A	119.3	N2—C16—H16C	109.5
C4—C3—H3A	119.3	H16A—C16—H16C	109.5
C5—C4—C3	120.29 (19)	H16B—C16—H16C	109.5
C5—C4—H4	119.9	N2—C17—H17A	109.5
C3—C4—H4	119.9	N2—C17—H17B	109.5
C4—C5—C6	120.34 (19)	H17A—C17—H17B	109.5
C4—C5—H5	119.8	N2—C17—H17C	109.5
C6—C5—H5	119.8	H17A—C17—H17C	109.5
C7—C6—C1	119.00 (17)	H17B—C17—H17C	109.5

N1—Sn1—O1—C10	17.16 (14)	C4—C5—C6—C1	−1.4 (3)
Cl4—Sn1—O1—C10	105.32 (14)	C1—C6—C7—C8	1.2 (3)
Cl3—Sn1—O1—C10	−160.75 (14)	C5—C6—C7—C8	−177.90 (19)
Cl2—Sn1—O1—C10	−66.72 (14)	C6—C7—C8—C9	−1.9 (3)
O1—Sn1—N1—C9	−16.03 (12)	C1—N1—C9—C8	2.9 (3)
Cl1—Sn1—N1—C9	160.11 (12)	Sn1—N1—C9—C8	−168.24 (16)
Cl4—Sn1—N1—C9	−107.40 (12)	C1—N1—C9—C10	−174.97 (16)
Cl3—Sn1—N1—C9	−9.9 (2)	Sn1—N1—C9—C10	13.9 (2)
Cl2—Sn1—N1—C9	72.90 (12)	C7—C8—C9—N1	−0.2 (3)
O1—Sn1—N1—C1	174.03 (17)	C7—C8—C9—C10	177.68 (17)
Cl1—Sn1—N1—C1	−9.83 (16)	Sn1—O1—C10—O2	167.37 (15)
Cl4—Sn1—N1—C1	82.65 (16)	Sn1—O1—C10—C9	−15.3 (2)
Cl3—Sn1—N1—C1	−179.84 (11)	N1—C9—C10—O2	176.83 (18)
Cl2—Sn1—N1—C1	−97.05 (16)	C8—C9—C10—O2	−1.1 (3)
C9—N1—C1—C2	174.22 (18)	N1—C9—C10—O1	−0.6 (3)
Sn1—N1—C1—C2	−16.6 (3)	C8—C9—C10—O1	−178.61 (17)
C9—N1—C1—C6	−3.6 (3)	C17—N2—C11—C15	−2.8 (3)
Sn1—N1—C1—C6	165.62 (14)	C16—N2—C11—C15	−169.76 (18)
N1—C1—C2—C3	−179.86 (18)	C17—N2—C11—C12	176.65 (18)
C6—C1—C2—C3	−2.1 (3)	C16—N2—C11—C12	9.6 (3)
C1—C2—C3—C4	−0.3 (3)	N2—C11—C12—C13	−178.67 (19)
C2—C3—C4—C5	1.8 (3)	C15—C11—C12—C13	0.8 (3)
C3—C4—C5—C6	−0.9 (3)	C14—N3—C13—C12	0.0 (3)
N1—C1—C6—C7	1.6 (3)	C11—C12—C13—N3	−0.5 (3)
C2—C1—C6—C7	−176.23 (18)	C13—N3—C14—C15	0.3 (3)
N1—C1—C6—C5	−179.32 (17)	N3—C14—C15—C11	−0.1 (3)
C2—C1—C6—C5	2.9 (3)	N2—C11—C15—C14	178.95 (19)
C4—C5—C6—C7	177.70 (19)	C12—C11—C15—C14	−0.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O1	0.87 (1)	1.98 (1)	2.816 (2)	160 (2)

Experimental details

Crystal data
Chemical formula	(C₇H₁₁N₂)[SnCl₄(C₁₀H₆NO₂)]
M_r	555.83
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	8.6681 (3), 8.8407 (4), 14.4447 (5)
α, β, γ (°)	96.721 (3), 91.924 (3), 108.038 (4)
V (Å³)	1042.43 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.76
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.621, 0.844
No. of measured, independent and observed [I > 2σ(I)] reflections	8056, 4610, 4202
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.021, 0.047, 1.06
No. of reflections	4610
No. of parameters	250
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)	0.52, −0.49

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
N3—H3···O1	0.87 (1)	1.98 (1)	2.816 (2)	160 (2)

Acknowledgements

We thank Shahid Beheshti 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
Najafi, E., Amini, M. M. & Ng, S. W. (2011). Acta Cryst. E67, m351. Web of Science CSD 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

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