N′-[(1E)-4-Bromo­benzyl­idene]-5-phenyl-1H-pyrazole-3-carbohydrazide

Karrouchi, K.; Ramli, Y.; Taoufik, J.; Radi, S.; Ansar, M.; Mague, J.T.

doi:10.1107/S2414314616008300

organic compounds

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ISSN: 2414-3146

Volume 1| Part 5| May 2016| x160830

doi:10.1107/S2414314616008300

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N′-[(1E)-4-Bromobenzylidene]-5-phenyl-1H-pyrazole-3-carbohydrazide

Khalid Karrouchi,^a Youssef Ramli,^a ^* Jamal Taoufik,^a Smaail Radi,^b Mhammed Ansar ^a and Joel T. Mague ^c

^aMedicinal Chemistry Laboratory, Faculty of Medicine and Pharmacy, Mohammed V University, Rabat, Morocco, ^bLCAE, Department of Chemistry, Faculty of Sciences, University Mohamed I, Oujda, Morocco, and ^cDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA
^*Correspondence e-mail: yramli76@yahoo.fr

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 8 May 2016; accepted 20 May 2016; online 24 May 2016)

In the title compound, C₁₇H₁₃BrN₄O, the dihedral angles between the pyrazole ring and the pedant phenyl and bromobenzene rings are 21.61 (11) and 28.09 (11)°, respectively. In the crystal, N—H⋯O hydrogen bonds link the molecules into [010] chains, which are reinforced by C—H⋯O interactions.

Keywords: crystal structure; pyrazole derivatives; C—H ⋯O hydrogen bonds.

CCDC reference: 1481143

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Chemical scheme

Structure description

As a continuation of our studies of pyrazole carbohydrazides (Karrouchi et al., 2015 ), we have studied the action of 4-bromobenzaldehyde towards 5-phenyl-1H-pyrazole-3-carbohydrazide. This readily leads to the title compound (Fig. 1) in good yield. The molecule is distinctly twisted from end to end as indicated by the dihedral angle of 21.61 (7)° between the pendant C1–C6 phenyl ring and the pyrazole ring, and the angle of 28.10 (7)° between the latter and the C12–C17 benzene ring.

Figure 1
The title molecule with labeling scheme and 50% probability ellipsoids.

In the crystal, a N1—H1A⋯O1 hydrogen bond links the molecules into chains running parallel to [010] (Table 1 and Fig. 2) with the chains stacking along the c axis direction (Fig. 3). The chain linkage is reinfoced by a weak C—H⋯O interaction.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯N2	0.90 (3)	2.45 (3)	2.787 (2)	103 (2)
N1—H1A⋯O1ⁱ	0.90 (3)	1.91 (3)	2.783 (2)	163 (3)
C6—H6⋯O1ⁱ	0.95	2.46	3.151 (3)	130
Symmetry code: (i) x, y-1, z.

Figure 2
A portion of one chain viewed along the c axis with the N—H⋯O hydrogen bonds shown as dotted lines.

Figure 3
Packing viewed along the b axis showing a stack of hydrogen-bonded chains.

Synthesis and crystallization

To a solution of 5-phenyl-1H-pyrazole-3-carbohydrazide (1 mmol, 250 mg) in 10 ml of ethanol, was added an equimolar amount of the 4-bromobenzaldehyde in the presence of acetic acid. The mixture was maintained under reflux for 2 h, until TLC indicated the end of reaction. Then, the mixture as poured into cold water, and the precipitate formed was filtered out washed with ethanol. Single crystals of the title compound were obtained on slow evaporation of the solvent (DMF). Yield 85%; m.p. 294–296°C

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The methyl group is rotationally disordered over two distinct sites. The two orientations were restrained to have comparable geometries.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₇H₁₃BrN₄O
M_r	369.22
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	150
a, b, c (Å)	15.5151 (3), 7.1752 (1), 14.4593 (3)
β (°)	110.072 (1)
V (Å³)	1511.90 (5)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	3.79
Crystal size (mm)	0.20 × 0.08 × 0.02

Data collection
Diffractometer	Bruker D8 VENTURE PHOTON 100 CMOS
Absorption correction	Multi-scan (SADABS; Bruker, 2016 )
T_min, T_max	0.74, 0.93
No. of measured, independent and observed [I > 2σ(I)] reflections	19026, 2958, 2704
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.076, 1.04
No. of reflections	2958
No. of parameters	216
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.63, −0.42
Computer programs: APEX3 and SAINT (Bruker, 2016), SHELXT (Sheldrick, 2015a ), SHELXL2014 (Sheldrick, 2015b ), DIAMOND (Brandenburg & Putz, 2012 ) and SHELXTL (Sheldrick, 2008 ).

Structural data

CCDC reference: 1481143

Crystal structure: contains datablocks global, I. DOI: 10.1107/S2414314616008300/hb4044sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2414314616008300/hb4044Isup2.hkl

checkCIF report

Experimental top

Structure description top

As a continuation of our studies of pyrazole carbohydrazides (Karrouchi et al., 2015), we have studied the action of 4-bromobenzaldehyde towards 5-phenyl-1H-pyrazole-3-carbohydrazide. This readily leads to the title compound (Fig. 1) in good yield. The molecule is distinctly twisted from end to end as indicated by the dihedral angle of 21.61 (7)° between the C1–C6 benzene ring and the pyrazole ring, and the angle of 28.10 (7)° between the latter and the C12–C17 benzene ring.

In the crystal, a N1—H1A···O1 hydrogen bond links the molecules into chains running parallel to [010] (Table 1 and Fig. 2) with the chains stacking along the c axis direction (Fig. 3). The chain linkage is reinfoced by a weak C—H···O interaction.

Computing details top

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The title molecule with labeling scheme and 50% probability ellipsoids.
	Fig. 2. A portion of one chain viewed along the c axis with the N—H···O hydrogen bonds shown as dotted lines.
	Fig. 3. Packing viewed along the b axis showing a stack of hydrogen-bonded chains.

N'-[(1E)-4-Bromobenzylidene]-5-phenyl-1H-pyrazole-3-carbohydrazide top

Crystal data top

C₁₇H₁₃BrN₄O	F(000) = 744
M_r = 369.22	D_x = 1.622 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54178 Å
a = 15.5151 (3) Å	Cell parameters from 9982 reflections
b = 7.1752 (1) Å	θ = 3.0–72.1°
c = 14.4593 (3) Å	µ = 3.79 mm⁻¹
β = 110.072 (1)°	T = 150 K
V = 1511.90 (5) Å³	Plate, colourless
Z = 4	0.20 × 0.08 × 0.02 mm

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	2958 independent reflections
Radiation source: INCOATEC IµS micro–focus source	2704 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.040
Detector resolution: 10.4167 pixels mm^-1	θ_max = 72.1°, θ_min = 3.0°
ω scans	h = −19→19
Absorption correction: multi-scan (SADABS; Bruker, 2016)	k = −8→8
T_min = 0.74, T_max = 0.93	l = −17→16
19026 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)] = 0.030	Hydrogen site location: mixed
wR(F²) = 0.076	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0406P)² + 1.1336P] where P = (F_o² + 2F_c²)/3
2958 reflections	(Δ/σ)_max = 0.001
216 parameters	Δρ_max = 0.63 e Å⁻³
0 restraints	Δρ_min = −0.42 e Å⁻³

Crystal data top

C₁₇H₁₃BrN₄O	V = 1511.90 (5) Å³
M_r = 369.22	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 15.5151 (3) Å	µ = 3.79 mm⁻¹
b = 7.1752 (1) Å	T = 150 K
c = 14.4593 (3) Å	0.20 × 0.08 × 0.02 mm
β = 110.072 (1)°

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	2958 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2016)	2704 reflections with I > 2σ(I)
T_min = 0.74, T_max = 0.93	R_int = 0.040
19026 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	0 restraints
wR(F²) = 0.076	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.63 e Å⁻³
2958 reflections	Δρ_min = −0.42 e Å⁻³
216 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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. H-atoms attached to carbon were placed in calculated positions (C—H = 0.95 - 0.98 Å) and included as riding contributions with isotropic displacement parameters 1.2 - 1.5 times those of the attached atoms. The methyl group is rotationally disordered over two distinct sites. The two orientations were restrained to have comparable geometries and included as riding contributions.

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

	x	y	z	U_iso*/U_eq
Br1	0.08242 (2)	1.44181 (3)	0.40787 (2)	0.03152 (10)
O1	0.55572 (10)	0.7240 (2)	0.39651 (12)	0.0274 (3)
N1	0.56205 (12)	0.1066 (2)	0.36792 (13)	0.0209 (3)
H1A	0.548 (2)	−0.014 (4)	0.372 (2)	0.037 (7)*
N2	0.50212 (11)	0.2396 (2)	0.37161 (12)	0.0207 (3)
N3	0.41822 (12)	0.5828 (2)	0.37237 (13)	0.0208 (3)
H3A	0.3856 (19)	0.477 (4)	0.3598 (19)	0.029 (7)*
N4	0.37729 (12)	0.7495 (2)	0.37822 (12)	0.0216 (3)
C1	0.72343 (14)	0.0664 (3)	0.36873 (14)	0.0201 (4)
C2	0.81039 (14)	0.1483 (3)	0.40431 (15)	0.0248 (4)
H2	0.8169	0.2714	0.4300	0.030*
C3	0.88713 (15)	0.0518 (3)	0.40256 (17)	0.0300 (5)
H3	0.9459	0.1090	0.4271	0.036*
C4	0.87849 (15)	−0.1286 (3)	0.36503 (16)	0.0289 (5)
H4	0.9311	−0.1948	0.3637	0.035*
C5	0.79246 (15)	−0.2107 (3)	0.32966 (15)	0.0254 (4)
H5	0.7863	−0.3337	0.3039	0.030*
C6	0.71507 (14)	−0.1153 (3)	0.33133 (15)	0.0219 (4)
H6	0.6565	−0.1733	0.3071	0.026*
C7	0.64455 (13)	0.1770 (3)	0.37096 (14)	0.0196 (4)
C8	0.63687 (14)	0.3686 (3)	0.37568 (15)	0.0208 (4)
H8	0.6821	0.4596	0.3781	0.025*
C9	0.54810 (14)	0.3990 (3)	0.37609 (15)	0.0194 (4)
C10	0.50863 (14)	0.5828 (3)	0.38258 (14)	0.0198 (4)
C11	0.28977 (14)	0.7463 (3)	0.35493 (15)	0.0218 (4)
H11	0.2566	0.6344	0.3322	0.026*
C12	0.24174 (14)	0.9165 (3)	0.36375 (14)	0.0207 (4)
C13	0.14574 (14)	0.9207 (3)	0.32523 (15)	0.0226 (4)
H13	0.1129	0.8155	0.2910	0.027*
C14	0.09828 (14)	1.0785 (3)	0.33688 (15)	0.0234 (4)
H14	0.0332	1.0824	0.3103	0.028*
C15	0.14737 (14)	1.2290 (3)	0.38761 (15)	0.0223 (4)
C16	0.24238 (14)	1.2301 (3)	0.42531 (15)	0.0234 (4)
H16	0.2746	1.3359	0.4596	0.028*
C17	0.28952 (14)	1.0742 (3)	0.41216 (15)	0.0223 (4)
H17	0.3547	1.0742	0.4361	0.027*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.03319 (15)	0.02154 (14)	0.03802 (15)	0.00873 (9)	0.00988 (10)	−0.00237 (9)
O1	0.0251 (7)	0.0134 (7)	0.0448 (9)	−0.0016 (6)	0.0134 (7)	−0.0016 (6)
N1	0.0225 (8)	0.0126 (8)	0.0281 (9)	0.0014 (6)	0.0093 (7)	0.0000 (7)
N2	0.0210 (8)	0.0128 (8)	0.0276 (9)	0.0022 (6)	0.0074 (7)	−0.0008 (6)
N3	0.0209 (8)	0.0136 (8)	0.0283 (9)	0.0006 (6)	0.0092 (7)	−0.0029 (7)
N4	0.0251 (9)	0.0160 (8)	0.0238 (8)	0.0044 (6)	0.0084 (7)	−0.0005 (6)
C1	0.0222 (10)	0.0191 (10)	0.0199 (9)	0.0035 (7)	0.0084 (8)	0.0012 (7)
C2	0.0264 (10)	0.0211 (10)	0.0264 (11)	−0.0006 (8)	0.0082 (8)	−0.0053 (8)
C3	0.0214 (10)	0.0364 (13)	0.0319 (11)	0.0007 (9)	0.0088 (9)	−0.0039 (9)
C4	0.0273 (11)	0.0324 (12)	0.0294 (11)	0.0088 (9)	0.0127 (9)	0.0007 (9)
C5	0.0320 (11)	0.0218 (10)	0.0247 (10)	0.0056 (8)	0.0128 (9)	0.0006 (8)
C6	0.0267 (10)	0.0183 (9)	0.0217 (10)	0.0008 (8)	0.0097 (8)	0.0009 (8)
C7	0.0216 (9)	0.0166 (9)	0.0208 (9)	0.0018 (7)	0.0077 (7)	0.0002 (7)
C8	0.0230 (10)	0.0136 (9)	0.0271 (10)	0.0000 (7)	0.0103 (8)	0.0011 (7)
C9	0.0227 (9)	0.0127 (9)	0.0227 (9)	0.0007 (7)	0.0076 (8)	0.0000 (7)
C10	0.0214 (9)	0.0163 (9)	0.0221 (9)	0.0012 (7)	0.0079 (8)	0.0009 (7)
C11	0.0235 (10)	0.0188 (10)	0.0234 (10)	−0.0002 (8)	0.0085 (8)	−0.0009 (8)
C12	0.0231 (10)	0.0200 (10)	0.0206 (9)	0.0032 (7)	0.0096 (8)	0.0024 (7)
C13	0.0216 (10)	0.0202 (10)	0.0264 (10)	−0.0028 (7)	0.0086 (8)	−0.0024 (8)
C14	0.0202 (9)	0.0248 (10)	0.0258 (10)	0.0020 (8)	0.0086 (8)	0.0014 (8)
C15	0.0265 (10)	0.0189 (10)	0.0224 (10)	0.0033 (8)	0.0094 (8)	0.0024 (8)
C16	0.0258 (10)	0.0197 (10)	0.0228 (10)	−0.0012 (8)	0.0059 (8)	0.0005 (8)
C17	0.0209 (9)	0.0235 (10)	0.0213 (9)	0.0012 (8)	0.0055 (8)	0.0010 (8)

Geometric parameters (Å, º) top

Br1—C15	1.907 (2)	C5—C6	1.389 (3)
O1—C10	1.225 (2)	C5—H5	0.9500
N1—N2	1.346 (2)	C6—H6	0.9500
N1—C7	1.362 (3)	C7—C8	1.384 (3)
N1—H1A	0.90 (3)	C8—C9	1.397 (3)
N2—C9	1.338 (3)	C8—H8	0.9500
N3—C10	1.359 (3)	C9—C10	1.470 (3)
N3—N4	1.370 (2)	C11—C12	1.459 (3)
N3—H3A	0.90 (3)	C11—H11	0.9500
N4—C11	1.282 (3)	C12—C13	1.400 (3)
C1—C2	1.398 (3)	C12—C17	1.401 (3)
C1—C6	1.400 (3)	C13—C14	1.392 (3)
C1—C7	1.468 (3)	C13—H13	0.9500
C2—C3	1.385 (3)	C14—C15	1.379 (3)
C2—H2	0.9500	C14—H14	0.9500
C3—C4	1.392 (3)	C15—C16	1.385 (3)
C3—H3	0.9500	C16—C17	1.385 (3)
C4—C5	1.386 (3)	C16—H16	0.9500
C4—H4	0.9500	C17—H17	0.9500

N2—N1—C7	112.98 (16)	C7—C8—H8	127.5
N2—N1—H1A	119.1 (19)	C9—C8—H8	127.5
C7—N1—H1A	127.4 (19)	N2—C9—C8	112.11 (17)
C9—N2—N1	104.11 (15)	N2—C9—C10	122.89 (18)
C10—N3—N4	118.45 (16)	C8—C9—C10	125.00 (18)
C10—N3—H3A	120.8 (17)	O1—C10—N3	123.57 (18)
N4—N3—H3A	120.7 (17)	O1—C10—C9	120.95 (18)
C11—N4—N3	116.10 (17)	N3—C10—C9	115.48 (17)
C2—C1—C6	118.90 (18)	N4—C11—C12	119.27 (19)
C2—C1—C7	118.12 (18)	N4—C11—H11	120.4
C6—C1—C7	122.97 (19)	C12—C11—H11	120.4
C3—C2—C1	120.7 (2)	C13—C12—C17	119.30 (18)
C3—C2—H2	119.6	C13—C12—C11	119.27 (18)
C1—C2—H2	119.7	C17—C12—C11	121.41 (18)
C2—C3—C4	120.2 (2)	C14—C13—C12	120.29 (19)
C2—C3—H3	119.9	C14—C13—H13	119.9
C4—C3—H3	119.9	C12—C13—H13	119.9
C5—C4—C3	119.4 (2)	C15—C14—C13	118.87 (19)
C5—C4—H4	120.3	C15—C14—H14	120.6
C3—C4—H4	120.3	C13—C14—H14	120.6
C4—C5—C6	120.8 (2)	C14—C15—C16	122.17 (19)
C4—C5—H5	119.6	C14—C15—Br1	118.98 (15)
C6—C5—H5	119.6	C16—C15—Br1	118.84 (16)
C5—C6—C1	119.9 (2)	C17—C16—C15	118.86 (19)
C5—C6—H6	120.0	C17—C16—H16	120.6
C1—C6—H6	120.0	C15—C16—H16	120.6
N1—C7—C8	105.89 (17)	C16—C17—C12	120.46 (19)
N1—C7—C1	125.45 (18)	C16—C17—H17	119.8
C8—C7—C1	128.65 (19)	C12—C17—H17	119.8
C7—C8—C9	104.91 (17)

C7—N1—N2—C9	0.6 (2)	C7—C8—C9—C10	178.65 (19)
C10—N3—N4—C11	170.82 (18)	N4—N3—C10—O1	−0.2 (3)
C6—C1—C2—C3	0.1 (3)	N4—N3—C10—C9	179.64 (17)
C7—C1—C2—C3	−178.9 (2)	N2—C9—C10—O1	172.58 (19)
C1—C2—C3—C4	0.1 (3)	C8—C9—C10—O1	−6.2 (3)
C2—C3—C4—C5	−0.1 (3)	N2—C9—C10—N3	−7.3 (3)
C3—C4—C5—C6	−0.1 (3)	C8—C9—C10—N3	173.97 (19)
C4—C5—C6—C1	0.3 (3)	N3—N4—C11—C12	177.16 (17)
C2—C1—C6—C5	−0.3 (3)	N4—C11—C12—C13	170.84 (19)
C7—C1—C6—C5	178.70 (18)	N4—C11—C12—C17	−10.8 (3)
N2—N1—C7—C8	−0.8 (2)	C17—C12—C13—C14	−1.4 (3)
N2—N1—C7—C1	179.63 (18)	C11—C12—C13—C14	176.94 (18)
C2—C1—C7—N1	−159.20 (19)	C12—C13—C14—C15	−0.6 (3)
C6—C1—C7—N1	21.8 (3)	C13—C14—C15—C16	1.6 (3)
C2—C1—C7—C8	21.3 (3)	C13—C14—C15—Br1	−177.73 (15)
C6—C1—C7—C8	−157.7 (2)	C14—C15—C16—C17	−0.5 (3)
N1—C7—C8—C9	0.6 (2)	Br1—C15—C16—C17	178.84 (15)
C1—C7—C8—C9	−179.86 (19)	C15—C16—C17—C12	−1.6 (3)
N1—N2—C9—C8	−0.2 (2)	C13—C12—C17—C16	2.6 (3)
N1—N2—C9—C10	−179.13 (18)	C11—C12—C17—C16	−175.78 (18)
C7—C8—C9—N2	−0.2 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···N2	0.90 (3)	2.45 (3)	2.787 (2)	103 (2)
N1—H1A···O1ⁱ	0.90 (3)	1.91 (3)	2.783 (2)	163 (3)
C6—H6···O1ⁱ	0.95	2.46	3.151 (3)	130

Symmetry code: (i) x, y−1, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···N2	0.90 (3)	2.45 (3)	2.787 (2)	103 (2)
N1—H1A···O1ⁱ	0.90 (3)	1.91 (3)	2.783 (2)	163 (3)
C6—H6···O1ⁱ	0.95	2.46	3.151 (3)	130

Symmetry code: (i) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₃BrN₄O
M_r	369.22
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	150
a, b, c (Å)	15.5151 (3), 7.1752 (1), 14.4593 (3)
β (°)	110.072 (1)
V (Å³)	1511.90 (5)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	3.79
Crystal size (mm)	0.20 × 0.08 × 0.02

Data collection
Diffractometer	Bruker D8 VENTURE PHOTON 100 CMOS
Absorption correction	Multi-scan (SADABS; Bruker, 2016)
T_min, T_max	0.74, 0.93
No. of measured, independent and observed [I > 2σ(I)] reflections	19026, 2958, 2704
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.076, 1.04
No. of reflections	2958
No. of parameters	216
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.63, −0.42

Computer programs: APEX3 (Bruker, 2016), SAINT (Bruker, 2016), SAINT (Bruker, 2016), SHELXT (Sheldrick, 2015a), SHELXL2014 (Sheldrick, 2015b), DIAMOND (Brandenburg & Putz, 2012), SHELXTL (Sheldrick, 2008).

Acknowledgements

The support of NSF–MRI Grant No. 1228232 for the purchase of the diffractometer and Tulane University for support of the Tulane Crystallography Laboratory are gratefully acknowledged.

References

Brandenburg, K. & Putz, H. (2012). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2016). APEX3, SAINT and SADABS. Bruker AXS, Inc., Madison, Wisconsin, USA. Google Scholar
Karrouchi, K., Ansar, M., Radi, S., Saadi, M. & El Ammari, L. (2015). Acta Cryst. E71, o890–o891. CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar

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