Crystal structure of 1-(4-fluoro­phen­yl)-4-(4-meth­oxy­phen­yl)-1H-1,2,3-triazole

Kumar, B.; Bhardwaj, M.; Paul, S.; Kant, R.; Gupta, V.K.

doi:10.1107/S2056989015012153

organic compounds

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Volume 71| Part 8| August 2015| Pages o534-o535

https://doi.org/10.1107/S2056989015012153

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Crystal structure of 1-(4-fluorophenyl)-4-(4-methoxyphenyl)-1H-1,2,3-triazole

Balbir Kumar,^a Madhvi Bhardwaj,^b Satya Paul,^b Rajni Kant ^a and Vivek K. Gupta ^a ^*

^aPost-Graduate Department of Physics & Electronics, University of Jammu, Jammu Tawi 180 006, India, and ^bDepartment of Chemistry, University of Jammu, Jammu Tawi 180 006, India
^*Correspondence e-mail: vivek_gupta2k2@hotmail.com

Edited by A. J. Lough, University of Toronto, Canada (Received 11 June 2015; accepted 24 June 2015; online 4 July 2015)

In the title compound, C₁₅H₁₂FN₃O, the triazole ring forms dihedral angles of 30.57 (8) and 21.81 (9)° with the fluoro-substituted and methoxy-substituted benzene rings, respectively. The dihedral angle between the benzene rings is 51.53 (7)°. In the crystal, π–π interactions between the triazole rings [centroid–centroid seperations = 3.774 (2) and 3.841 (2) Å] form chains along [010].

Keywords: crystal structure; 1,2,3-triazole; π–π interactions.

CCDC reference: 1408544

1. Related literature

For related literature on 1,2,3-triazoles, see: Aher et al. (2009 ); Jordao et al. (2009 ); Vijaya Raghava Reddy et al. (2010 ); Soltis et al. (1996 ). For applications of 1,2,3-triazoles, see: Pérez-Balderas et al. (2003 ); Wu et al. (2004 ); Kumar & Pandey (2008 ); Haridas et al. (2008 ); Turner et al., (2007 ); Angell & Burgess (2007 ); For the synthesis of 1,2,3-triazoles, see: Huisgen et al. (1965 ); Wang et al. (2010 ). For related structures, see: Abdel-Wahab et al. (2012 ); Zhang et al. (2004 ).

2. Experimental

2.1. Crystal data

C₁₅H₁₂FN₃O
M_r = 269.28
Triclinic, $[P \overline 1]$
a = 5.6572 (5) Å
b = 7.3692 (8) Å
c = 15.5711 (15) Å
α = 79.202 (9)°
β = 81.159 (8)°
γ = 89.442 (8)°
V = 629.95 (11) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.20 mm

2.2. Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.806, T_max = 1.000
4369 measured reflections
2461 independent reflections
1575 reflections with I > 2σ(I)
R_int = 0.034

2.3. Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.179
S = 1.04
2461 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 1408544

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: https://doi.org/10.1107/S2056989015012153/lh5772sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015012153/lh5772Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015012153/lh5772Isup3.cml

checkCIF report

Comment top

1,2,3-Triazoles are an important class of organic compounds which have become prominent in recent years as superbly versatile five membered nitrogen heterocycles. The 1,2,3-triazole family exhibit a broad spectrum of bioactivities such as antifungal (Aher et al., 2009) antiviral (Jordao et al., 2009), antibacterial (Vijaya Raghava Reddy et al., 2010) and anticancer (Soltis et al., 1996) activities. Furthermore 1,4-disubstituted 1,2,3-triazoles have also been used as a ligation tool for the synthesis of neoglyco-conjugates (Perez-Balderas et al., 2003), multivalent dendrimeric peptides (Wu et al., 2004), ionic receptors (Kumar et al., 2008), triazolophanes (Haridas et al., 2008), cyclic peptides (Turner et al., 2007) and peptidomimetics (Angell et al., 2007). 1,2,3-Triazoles are traditionally obtained using the thermal 1,3-dipolar cycloaddition of organic azides with alkynes (Huisgen et al., 1965) that has been known for nearly five decades. Recently, copper based catalysis was found to dramatically accelerate the reaction under mild conditions while achieving a high regioselectivity towards the 1,4-regioisomer of the triazole product (Wang et al., 2010). This powerful, highly reliable, and selective reaction is the paradigm of a click reaction, which placed it in a class of its own and has enabled many novel applications.

The molecular structure of the title compound is shown in Fig. 1. The triazole ring forms dihedral angles of 30.57 (8)° and 21.81 (9)° with the fluoro-substituted and methoxy-substituted benzen rings, respectively. The dihedral angle between the benzene rings is 51.53 (7)°. All bond lengths and angles are normal and correspond to those observed in the related structures (Zhang et al., 2004; Abdel-Wahab et al., 2012). The C15—F1 bond length [1.357 (4) Å] agrees well with the accepted value of 1.340 Å for the F-C_aromatic length and is in good agreement with a structure of this type (Abdel-Wahab et al., 2012). In the crystal, π–π interactions observed between the triazole rings [centroid–centroid seperations = 3.774 (2) and 3.841 (2) Å] form chains along [010] (Fig. 2).

Related literature top

For related literature on 1,2,3-triazoles, see: Aher et al. (2009); Jordao et al. (2009); Vijaya Raghava Reddy et al. (2010); Soltis et al. (1996). For applications of 1,2,3-triazoles, see: Pérez-Balderas et al. (2003); Wu et al. (2004); Kumar & Pandey (2008); Haridas et al. (2008); Turner et al., (2007); Angell & Burgess (2007); For the synthesis of 1,2,3-triazoles, see: Huisgen et al. (1965); Wang et al. (2010). For related structures, see: Abdel-Wahab et al. (2012); Zhang et al. (2004).

Experimental top

Synthesis of 1-(4-flourophenyl)-4-(4-methoxyphenyl) -1H-1,2,3-triazole: To 4-fluoroaniline (0.22 g, 2 mmol) in a round bottomed flask maintained at 273-278 K, mixture of conc. HCl: H₂O (1.5 ml, 1:1) was added and stirred for 5 min. Then solution of NaNO₂ (0.17 g, 2.5 mmol in 1 ml water) was added dropwise over a period of 5 min. After stirring for another 5 min, sodium azide (0.19 g, 3 mmol) was added and the reaction mixture was further stirred for another 10 min. Finally, 4-methoxyphenylacetylene (0.19 g, 1.5 mmol) and catalyst [Cu(0)-Fe₃O₄@SiO₂/NH₂Cel] (0.05 g) were added to the reaction mixture followed by stirring at room temperature for 6 h. The reaction was then stopped and the catalyst was separated using an external magnet. The reaction mixture was extracted with EtOAc, washed with water and dried over Na₂SO₄. Finally, the product was obtained after removal of the solvent under reduced pressure followed by crystallization with EtOAc: pet ether. The product, 1-(4-flourophenyl)-4-(4-methoxyphenyl) -1H-1,2,3-triazole was obtained as shiny white crystals.

Structure description top

For related literature on 1,2,3-triazoles, see: Aher et al. (2009); Jordao et al. (2009); Vijaya Raghava Reddy et al. (2010); Soltis et al. (1996). For applications of 1,2,3-triazoles, see: Pérez-Balderas et al. (2003); Wu et al. (2004); Kumar & Pandey (2008); Haridas et al. (2008); Turner et al., (2007); Angell & Burgess (2007); For the synthesis of 1,2,3-triazoles, see: Huisgen et al. (1965); Wang et al. (2010). For related structures, see: Abdel-Wahab et al. (2012); Zhang et al. (2004).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 40% probability level. H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. The packing arrangement of molecules viewed along the a axis.

1-(4-Fluorophenyl)-4-(4-methoxyphenyl)-1H-1,2,3-triazole top

Crystal data top

C₁₅H₁₂FN₃O	Z = 2
M_r = 269.28	F(000) = 280
Triclinic, P1	D_x = 1.420 Mg m⁻³ D_m = 1.42 Mg m⁻³ D_m measured by not measured
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.6572 (5) Å	Cell parameters from 1205 reflections
b = 7.3692 (8) Å	θ = 4.0–28.0°
c = 15.5711 (15) Å	µ = 0.10 mm⁻¹
α = 79.202 (9)°	T = 293 K
β = 81.159 (8)°	Block, white
γ = 89.442 (8)°	0.30 × 0.20 × 0.20 mm
V = 629.95 (11) Å³

Data collection top

Oxford Diffraction Xcalibur Sapphire3 diffractometer	2461 independent reflections
Radiation source: fine-focus sealed tube	1575 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
Detector resolution: 16.1049 pixels mm^-1	θ_max = 26.0°, θ_min = 3.7°
ω scans	h = −4→6
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −7→9
T_min = 0.806, T_max = 1.000	l = −18→19
4369 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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.179	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0744P)² + 0.0652P] where P = (F_o² + 2F_c²)/3
2461 reflections	(Δ/σ)_max < 0.001
182 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₅H₁₂FN₃O	γ = 89.442 (8)°
M_r = 269.28	V = 629.95 (11) Å³
Triclinic, P1	Z = 2
a = 5.6572 (5) Å	Mo Kα radiation
b = 7.3692 (8) Å	µ = 0.10 mm⁻¹
c = 15.5711 (15) Å	T = 293 K
α = 79.202 (9)°	0.30 × 0.20 × 0.20 mm
β = 81.159 (8)°

Data collection top

Oxford Diffraction Xcalibur Sapphire3 diffractometer	2461 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	1575 reflections with I > 2σ(I)
T_min = 0.806, T_max = 1.000	R_int = 0.034
4369 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	0 restraints
wR(F²) = 0.179	H-atom parameters constrained
S = 1.04	Δρ_max = 0.26 e Å⁻³
2461 reflections	Δρ_min = −0.22 e Å⁻³
182 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
F1	0.2052 (4)	−0.1487 (2)	0.41281 (12)	0.0782 (6)
N1	0.1232 (4)	0.1852 (3)	0.07275 (13)	0.0404 (5)
N2	−0.0970 (4)	0.1982 (3)	0.04842 (15)	0.0505 (6)
N3	−0.0714 (4)	0.2743 (3)	−0.03467 (15)	0.0489 (6)
C4	0.1657 (4)	0.3132 (3)	−0.06593 (16)	0.0367 (6)
C5	0.2893 (4)	0.2552 (3)	0.00235 (15)	0.0395 (6)
H5	0.4540	0.2623	0.0009	0.047*
C6	0.2436 (4)	0.3971 (3)	−0.15737 (16)	0.0371 (6)
C7	0.1015 (5)	0.3849 (3)	−0.22101 (17)	0.0426 (6)
H7	−0.0454	0.3228	−0.2040	0.051*
C8	0.1707 (5)	0.4613 (4)	−0.30769 (18)	0.0483 (7)
H8	0.0717	0.4501	−0.3490	0.058*
C9	0.3880 (5)	0.5558 (3)	−0.33479 (17)	0.0457 (7)
O9	0.4360 (4)	0.6328 (3)	−0.42195 (14)	0.0718 (7)
C10	0.5341 (5)	0.5698 (3)	−0.27319 (17)	0.0452 (6)
H10	0.6804	0.6327	−0.2906	0.054*
C11	0.4626 (5)	0.4900 (3)	−0.18530 (16)	0.0414 (6)
H11	0.5629	0.4987	−0.1441	0.050*
C12	0.1484 (4)	0.1035 (3)	0.16056 (16)	0.0371 (6)
C13	−0.0340 (5)	0.1177 (3)	0.22842 (16)	0.0430 (6)
H13	−0.1694	0.1844	0.2166	0.052*
C14	−0.0162 (5)	0.0338 (4)	0.31322 (18)	0.0518 (7)
H14	−0.1391	0.0417	0.3594	0.062*
C15	0.1878 (5)	−0.0630 (3)	0.32897 (18)	0.0500 (7)
C16	0.3719 (5)	−0.0751 (3)	0.26282 (19)	0.0503 (7)
H16	0.5088	−0.1392	0.2752	0.060*
C17	0.3531 (5)	0.0081 (3)	0.17797 (17)	0.0425 (6)
H17	0.4773	0.0007	0.1322	0.051*
C18	0.6617 (8)	0.6997 (5)	−0.4596 (2)	0.0918 (12)
H18A	0.7031	0.7988	−0.4321	0.138*
H18B	0.6648	0.7446	−0.5218	0.138*
H18C	0.7749	0.6025	−0.4512	0.138*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0830 (15)	0.0859 (12)	0.0607 (12)	0.0042 (11)	−0.0198 (10)	0.0062 (9)
N1	0.0268 (11)	0.0459 (12)	0.0481 (13)	0.0005 (9)	−0.0039 (9)	−0.0096 (9)
N2	0.0252 (11)	0.0691 (14)	0.0558 (15)	−0.0006 (10)	−0.0048 (10)	−0.0098 (11)
N3	0.0260 (12)	0.0675 (15)	0.0508 (14)	−0.0006 (11)	−0.0033 (10)	−0.0069 (11)
C4	0.0268 (13)	0.0389 (12)	0.0455 (15)	0.0003 (10)	−0.0056 (10)	−0.0105 (10)
C5	0.0224 (12)	0.0470 (14)	0.0483 (15)	−0.0018 (11)	−0.0025 (10)	−0.0090 (11)
C6	0.0279 (13)	0.0391 (12)	0.0458 (15)	0.0054 (10)	−0.0075 (11)	−0.0108 (10)
C7	0.0303 (13)	0.0450 (13)	0.0536 (16)	−0.0001 (11)	−0.0086 (11)	−0.0107 (11)
C8	0.0393 (15)	0.0583 (16)	0.0513 (17)	0.0049 (13)	−0.0158 (13)	−0.0136 (12)
C9	0.0450 (16)	0.0499 (14)	0.0404 (15)	0.0101 (13)	−0.0063 (12)	−0.0049 (11)
O9	0.0608 (14)	0.0911 (15)	0.0542 (13)	−0.0043 (12)	−0.0021 (11)	0.0045 (11)
C10	0.0321 (14)	0.0458 (14)	0.0553 (17)	−0.0029 (12)	0.0001 (12)	−0.0083 (12)
C11	0.0331 (14)	0.0447 (13)	0.0484 (15)	0.0003 (11)	−0.0088 (11)	−0.0120 (11)
C12	0.0293 (13)	0.0358 (12)	0.0458 (15)	−0.0034 (10)	−0.0048 (11)	−0.0070 (10)
C13	0.0316 (13)	0.0452 (14)	0.0497 (16)	0.0032 (11)	−0.0020 (11)	−0.0063 (11)
C14	0.0441 (16)	0.0556 (16)	0.0522 (18)	0.0000 (14)	0.0027 (13)	−0.0092 (12)
C15	0.0532 (18)	0.0471 (15)	0.0493 (17)	−0.0049 (13)	−0.0165 (14)	−0.0011 (12)
C16	0.0401 (15)	0.0457 (14)	0.0657 (19)	0.0059 (12)	−0.0131 (14)	−0.0079 (13)
C17	0.0317 (13)	0.0425 (13)	0.0535 (16)	0.0001 (11)	−0.0038 (11)	−0.0121 (11)
C18	0.091 (3)	0.109 (3)	0.068 (2)	−0.032 (2)	0.000 (2)	−0.0060 (19)

Geometric parameters (Å, º) top

F1—C15	1.357 (3)	O9—C18	1.376 (4)
N1—C5	1.354 (3)	C10—C11	1.384 (3)
N1—N2	1.354 (3)	C10—H10	0.9300
N1—C12	1.415 (3)	C11—H11	0.9300
N2—N3	1.297 (3)	C12—C13	1.377 (3)
N3—C4	1.368 (3)	C12—C17	1.385 (3)
C4—C5	1.362 (3)	C13—C14	1.367 (3)
C4—C6	1.444 (3)	C13—H13	0.9300
C5—H5	0.9300	C14—C15	1.381 (4)
C6—C7	1.384 (3)	C14—H14	0.9300
C6—C11	1.390 (3)	C15—C16	1.363 (4)
C7—C8	1.360 (3)	C16—C17	1.368 (3)
C7—H7	0.9300	C16—H16	0.9300
C8—C9	1.387 (4)	C17—H17	0.9300
C8—H8	0.9300	C18—H18A	0.9600
C9—O9	1.356 (3)	C18—H18B	0.9600
C9—C10	1.377 (4)	C18—H18C	0.9600

C5—N1—N2	109.5 (2)	C10—C11—C6	121.3 (2)
C5—N1—C12	130.8 (2)	C10—C11—H11	119.4
N2—N1—C12	119.7 (2)	C6—C11—H11	119.4
N3—N2—N1	107.7 (2)	C13—C12—C17	120.3 (2)
N2—N3—C4	109.6 (2)	C13—C12—N1	119.3 (2)
C5—C4—N3	107.4 (2)	C17—C12—N1	120.4 (2)
C5—C4—C6	131.8 (2)	C14—C13—C12	120.1 (2)
N3—C4—C6	120.8 (2)	C14—C13—H13	120.0
N1—C5—C4	105.8 (2)	C12—C13—H13	120.0
N1—C5—H5	127.1	C13—C14—C15	118.7 (2)
C4—C5—H5	127.1	C13—C14—H14	120.7
C7—C6—C11	117.5 (2)	C15—C14—H14	120.7
C7—C6—C4	120.5 (2)	F1—C15—C16	119.1 (2)
C11—C6—C4	122.0 (2)	F1—C15—C14	119.0 (3)
C8—C7—C6	121.9 (3)	C16—C15—C14	121.9 (3)
C8—C7—H7	119.1	C15—C16—C17	119.2 (2)
C6—C7—H7	119.1	C15—C16—H16	120.4
C7—C8—C9	120.3 (2)	C17—C16—H16	120.4
C7—C8—H8	119.9	C16—C17—C12	119.7 (2)
C9—C8—H8	119.9	C16—C17—H17	120.1
O9—C9—C10	125.0 (3)	C12—C17—H17	120.1
O9—C9—C8	115.6 (3)	O9—C18—H18A	109.5
C10—C9—C8	119.3 (2)	O9—C18—H18B	109.5
C9—O9—C18	120.7 (3)	H18A—C18—H18B	109.5
C9—C10—C11	119.8 (3)	O9—C18—H18C	109.5
C9—C10—H10	120.1	H18A—C18—H18C	109.5
C11—C10—H10	120.1	H18B—C18—H18C	109.5

C5—N1—N2—N3	−0.1 (3)	O9—C9—C10—C11	178.0 (2)
C12—N1—N2—N3	−178.86 (19)	C8—C9—C10—C11	−0.1 (4)
N1—N2—N3—C4	−0.3 (3)	C9—C10—C11—C6	−0.7 (4)
N2—N3—C4—C5	0.6 (3)	C7—C6—C11—C10	1.0 (3)
N2—N3—C4—C6	179.3 (2)	C4—C6—C11—C10	−179.9 (2)
N2—N1—C5—C4	0.5 (2)	C5—N1—C12—C13	150.9 (2)
C12—N1—C5—C4	179.1 (2)	N2—N1—C12—C13	−30.7 (3)
N3—C4—C5—N1	−0.7 (2)	C5—N1—C12—C17	−30.0 (3)
C6—C4—C5—N1	−179.1 (2)	N2—N1—C12—C17	148.5 (2)
C5—C4—C6—C7	156.9 (2)	C17—C12—C13—C14	−1.6 (4)
N3—C4—C6—C7	−21.4 (3)	N1—C12—C13—C14	177.6 (2)
C5—C4—C6—C11	−22.2 (4)	C12—C13—C14—C15	0.6 (4)
N3—C4—C6—C11	159.5 (2)	C13—C14—C15—F1	−179.1 (2)
C11—C6—C7—C8	−0.4 (3)	C13—C14—C15—C16	0.8 (4)
C4—C6—C7—C8	−179.5 (2)	F1—C15—C16—C17	178.8 (2)
C6—C7—C8—C9	−0.4 (4)	C14—C15—C16—C17	−1.2 (4)
C7—C8—C9—O9	−177.6 (2)	C15—C16—C17—C12	0.1 (4)
C7—C8—C9—C10	0.7 (4)	C13—C12—C17—C16	1.2 (4)
C10—C9—O9—C18	14.0 (4)	N1—C12—C17—C16	−177.9 (2)
C8—C9—O9—C18	−167.9 (3)

Experimental details

Crystal data
Chemical formula	C₁₅H₁₂FN₃O
M_r	269.28
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	5.6572 (5), 7.3692 (8), 15.5711 (15)
α, β, γ (°)	79.202 (9), 81.159 (8), 89.442 (8)
V (Å³)	629.95 (11)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Oxford Diffraction Xcalibur Sapphire3
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)
T_min, T_max	0.806, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	4369, 2461, 1575
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.179, 1.04
No. of reflections	2461
No. of parameters	182
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.22

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), PLATON (Spek, 2009).

Acknowledgements

RK acknowledges the Department of Science & Technology for the single-crystal X-ray diffractometer sanctioned as a National Facility under Project No. SR/S2/CMP-47/2003.

References

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