5-Methyl-N′-[(Z)-4-methyl­benzyl­idene]-1H-pyrazole-3-carbohydrazide

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

doi:10.1107/S2414314616007938

organic compounds

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ISSN: 2414-3146

Volume 1| Part 5| May 2016| x160793

doi:10.1107/S2414314616007938

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5-Methyl-N′-[(Z)-4-methylbenzylidene]-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 14 May 2016; online 20 May 2016)

The title 1-H-pyrazole-3-carbohydrazide molecule, C₁₃H₁₄N₄O, shows a slight twist from end to end. The packing features N—H⋯N and bifurcated N—H⋯(N,O) hydrogen bonds, which generate (010) sheets.

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

CCDC reference: 1479830

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Chemical scheme

Structure description

As a continuation of our research work devoted to the development of pyrazole carbohydrazides (Karrouchi et al., 2015 ), the title compound was prepared and characterized by single-crystal X-ray diffraction.

The title molecule Fig. 1 is slightly bowed, as well as slightly twisted, from end to end. This can be seen from the dihedral angle of 8.32 (7)° between the five- and six-membered rings. The packing is directed by N—H⋯N and bifurcated N—H⋯(N,O) hydrogen bonds (Table 1 and Figs. 2 and 3), which generate (010) sheets.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1ⁱ	0.905 (18)	2.191 (18)	2.8655 (13)	130.8 (14)
N1—H1N⋯N4ⁱ	0.905 (18)	2.395 (18)	3.2419 (14)	155.9 (15)
N3—H3N⋯O1ⁱⁱ	0.885 (18)	2.232 (18)	2.9971 (13)	144.4 (15)
Symmetry codes: (i) $[x-1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Figure 1
The title molecule shown with 50% probability displacement ellipsoids.

Figure 2
Packing viewed along the a axis, with intermolecular N—H⋯N and N—H⋯O hydrogen bonds shown as dotted lines.

Figure 3
Packing viewed along the c axis, with intermolecular N—H⋯N and N—H⋯O hydrogen bonds shown as dotted lines.

Synthesis and crystallization

To a solution of 5-methyl-1H-pyrazole-3-carbohydrazide (1 mmol, 250 mg) in 10 ml of ethanol was added an equimolar amount of 4-bromobenzaldehyde in the presence of acetic acid. The mixture was maintained under reflux for 2 h, until thin-layer chromatography (TLC) indicated the end of the reaction. The mixture was then poured into cold water and the precipitate which formed was filtered off washed with ethanol. Single crystals of the title compound were obtained on slow evaporation of a DMF solution [yield 59%; m.p. 565–567 K (methanol/DMF)].

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The methyl group on the phenyl ring is rotationally disordered and refined with a SHELX AFIX 123 instruction.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₃H₁₄N₄O
M_r	242.28
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	150
a, b, c (Å)	6.3283 (1), 19.6204 (4), 10.1245 (2)
β (°)	105.746 (1)
V (Å³)	1209.92 (4)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	0.72
Crystal size (mm)	0.18 × 0.11 × 0.05

Data collection
Diffractometer	Bruker D8 VENTURE PHOTON 100 CMOS
Absorption correction	Multi-scan (SADABS; Bruker, 2016 )
T_min, T_max	0.88, 0.96
No. of measured, independent and observed [I > 2σ(I)] reflections	13389, 2396, 2144
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.618

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.091, 1.05
No. of reflections	2396
No. of parameters	174
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.22
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: 1479830

Crystal structure: contains datablocks global, I. DOI: 10.1107/S2414314616007938/hb4045sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2414314616007938/hb4045Isup2.hkl

Supporting information file. DOI: 10.1107/S2414314616007938/hb4045Isup3.cml

checkCIF report

Experimental top

To a solution of 5-methyl-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 thin-layer chromatography (TLC) indicated the end of reaction. The mixture as then poured into cold water and the precipitate formed was filtered off washed with ethanol. Single crystals of the title compound were obtained on slow evaporation of a DMF solution [yield 59%; m.p. 565–567 K (methanol/DMF)].

Structure description top

As a continuation of our research work devoted to the development of pyrazole carbohydrazide (Karrouchi et al., 2015), the title compound was prepared and characterized by single-crystal X-ray diffraction.

The title molecule is slightly bowed as well as slightly twisted from end to end. This can be seen from the dihedral angle of 8.32 (7)° between the five- and six-membered rings. The packing is directed by N—H···N and bifurcated N—H···(N,O) hydrogen bonds (Table 1 and Figs. 2 and 3), which generate (010) sheets.

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 shown with 50% probability displacement ellipsoids.
	Fig. 2. Packing viewed along the a axis with intermolecular N—H···N and N—H···O hydrogen bonds shown as dotted lines.
	Fig. 3. Packing viewed along the c axis with intermolecular N—H···N and N—H···O hydrogen bonds shown as dotted lines.

5-Methyl-N'-[(Z)-4-methylbenzylidene]-1H-pyrazole-3-carbohydrazide top

Crystal data top

C₁₃H₁₄N₄O	F(000) = 512
M_r = 242.28	D_x = 1.330 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54178 Å
a = 6.3283 (1) Å	Cell parameters from 9985 reflections
b = 19.6204 (4) Å	θ = 4.5–72.4°
c = 10.1245 (2) Å	µ = 0.72 mm⁻¹
β = 105.746 (1)°	T = 150 K
V = 1209.92 (4) Å³	Slab, colourless
Z = 4	0.18 × 0.11 × 0.05 mm

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	2396 independent reflections
Radiation source: INCOATEC IµS micro–focus source	2144 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.036
Detector resolution: 10.4167 pixels mm^-1	θ_max = 72.4°, θ_min = 4.5°
ω scans	h = −7→7
Absorption correction: multi-scan (SADABS; Bruker, 2016)	k = −22→24
T_min = 0.88, T_max = 0.96	l = −12→12
13389 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.091	w = 1/[σ²(F_o²) + (0.0415P)² + 0.4538P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
2396 reflections	Δρ_max = 0.24 e Å⁻³
174 parameters	Δρ_min = −0.22 e Å⁻³
0 restraints	Extinction correction: SHELXL2014 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0028 (4)

Crystal data top

C₁₃H₁₄N₄O	V = 1209.92 (4) Å³
M_r = 242.28	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 6.3283 (1) Å	µ = 0.72 mm⁻¹
b = 19.6204 (4) Å	T = 150 K
c = 10.1245 (2) Å	0.18 × 0.11 × 0.05 mm
β = 105.746 (1)°

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	2396 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2016)	2144 reflections with I > 2σ(I)
T_min = 0.88, T_max = 0.96	R_int = 0.036
13389 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.091	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.24 e Å⁻³
2396 reflections	Δρ_min = −0.22 e Å⁻³
174 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 on the phenyl ring is rotationally disordered and refined with a SHELX AFIX 123 instruction.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.13164 (14)	0.25617 (5)	0.45005 (8)	0.0234 (2)
N1	−0.45027 (16)	0.19423 (5)	0.10816 (10)	0.0219 (2)
H1N	−0.548 (3)	0.1943 (9)	0.0242 (18)	0.041 (5)*
N2	−0.26056 (16)	0.22876 (5)	0.12750 (10)	0.0230 (2)
N3	0.13616 (16)	0.28777 (5)	0.23431 (10)	0.0199 (2)
H3N	0.075 (3)	0.2822 (9)	0.1453 (19)	0.040 (5)*
N4	0.33063 (16)	0.32301 (5)	0.28110 (10)	0.0197 (2)
C1	−0.6798 (2)	0.12747 (7)	0.22526 (13)	0.0257 (3)
H1A	−0.7097	0.1311	0.3150	0.038*
H1B	−0.6543	0.0796	0.2064	0.038*
H1C	−0.8061	0.1448	0.1541	0.038*
C2	−0.48123 (19)	0.16845 (6)	0.22564 (12)	0.0194 (3)
C3	−0.29917 (19)	0.18685 (6)	0.32884 (12)	0.0202 (3)
H3A	−0.2692	0.1768	0.4239	0.024*
C4	−0.16778 (18)	0.22376 (6)	0.26275 (11)	0.0181 (2)
C5	0.04539 (18)	0.25684 (6)	0.32520 (11)	0.0183 (2)
C6	0.3987 (2)	0.35207 (6)	0.18704 (12)	0.0215 (3)
H6	0.3148	0.3475	0.0942	0.026*
C7	0.60155 (19)	0.39211 (6)	0.21779 (12)	0.0208 (3)
C8	0.7525 (2)	0.39328 (6)	0.34711 (13)	0.0254 (3)
H8	0.7255	0.3672	0.4199	0.031*
C9	0.9410 (2)	0.43211 (7)	0.36968 (13)	0.0274 (3)
H9	1.0421	0.4322	0.4583	0.033*
C10	0.9870 (2)	0.47127 (6)	0.26588 (13)	0.0251 (3)
C11	0.8371 (2)	0.46969 (7)	0.13747 (13)	0.0274 (3)
H11	0.8646	0.4958	0.0648	0.033*
C12	0.6474 (2)	0.43060 (6)	0.11315 (12)	0.0249 (3)
H12	0.5476	0.4301	0.0241	0.030*
C13	1.1923 (2)	0.51398 (8)	0.29335 (16)	0.0362 (3)
H13A	1.2769	0.5084	0.3893	0.054*	0.514 (19)
H13B	1.2813	0.4993	0.2330	0.054*	0.514 (19)
H13C	1.1521	0.5620	0.2756	0.054*	0.514 (19)
H13E	1.1966	0.5380	0.2093	0.054*	0.486 (19)
H13D	1.1923	0.5472	0.3656	0.054*	0.486 (19)
H13F	1.3214	0.4845	0.3230	0.054*	0.486 (19)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0202 (4)	0.0333 (5)	0.0147 (4)	−0.0029 (3)	0.0013 (3)	0.0003 (3)
N1	0.0180 (5)	0.0285 (5)	0.0162 (5)	−0.0025 (4)	−0.0004 (4)	0.0007 (4)
N2	0.0190 (5)	0.0311 (6)	0.0169 (5)	−0.0040 (4)	0.0016 (4)	0.0023 (4)
N3	0.0182 (5)	0.0250 (5)	0.0150 (5)	−0.0042 (4)	0.0020 (4)	−0.0008 (4)
N4	0.0171 (5)	0.0214 (5)	0.0201 (5)	−0.0015 (4)	0.0039 (4)	−0.0016 (4)
C1	0.0216 (6)	0.0269 (6)	0.0273 (6)	−0.0040 (5)	0.0046 (5)	−0.0006 (5)
C2	0.0190 (6)	0.0190 (5)	0.0199 (6)	0.0012 (4)	0.0049 (4)	−0.0002 (4)
C3	0.0211 (6)	0.0226 (6)	0.0164 (5)	−0.0008 (4)	0.0040 (4)	0.0004 (4)
C4	0.0174 (5)	0.0202 (5)	0.0155 (5)	0.0013 (4)	0.0023 (4)	−0.0001 (4)
C5	0.0172 (5)	0.0202 (5)	0.0167 (5)	0.0019 (4)	0.0035 (4)	−0.0003 (4)
C6	0.0223 (6)	0.0231 (6)	0.0184 (5)	−0.0008 (5)	0.0044 (4)	−0.0013 (4)
C7	0.0210 (6)	0.0194 (6)	0.0228 (6)	0.0007 (4)	0.0075 (5)	−0.0013 (4)
C8	0.0267 (6)	0.0260 (6)	0.0230 (6)	−0.0025 (5)	0.0056 (5)	0.0038 (5)
C9	0.0246 (6)	0.0277 (6)	0.0265 (6)	−0.0015 (5)	0.0011 (5)	0.0015 (5)
C10	0.0232 (6)	0.0204 (6)	0.0341 (7)	−0.0004 (5)	0.0119 (5)	−0.0029 (5)
C11	0.0325 (7)	0.0265 (6)	0.0273 (6)	−0.0033 (5)	0.0150 (5)	0.0014 (5)
C12	0.0273 (6)	0.0278 (6)	0.0199 (6)	−0.0011 (5)	0.0069 (5)	−0.0004 (5)
C13	0.0303 (7)	0.0333 (7)	0.0474 (9)	−0.0089 (6)	0.0144 (6)	−0.0041 (6)

Geometric parameters (Å, º) top

O1—C5	1.2335 (14)	C6—H6	0.9500
N1—N2	1.3457 (14)	C7—C12	1.3941 (17)
N1—C2	1.3547 (15)	C7—C8	1.3960 (17)
N1—H1N	0.905 (18)	C8—C9	1.3813 (18)
N2—C4	1.3390 (14)	C8—H8	0.9500
N3—C5	1.3535 (15)	C9—C10	1.3949 (18)
N3—N4	1.3786 (13)	C9—H9	0.9500
N3—H3N	0.885 (18)	C10—C11	1.3863 (18)
N4—C6	1.2808 (15)	C10—C13	1.5068 (17)
C1—C2	1.4911 (16)	C11—C12	1.3893 (18)
C1—H1A	0.9800	C11—H11	0.9500
C1—H1B	0.9800	C12—H12	0.9500
C1—H1C	0.9800	C13—H13A	0.9800
C2—C3	1.3770 (16)	C13—H13B	0.9800
C3—C4	1.4020 (16)	C13—H13C	0.9800
C3—H3A	0.9500	C13—H13E	0.9800
C4—C5	1.4757 (15)	C13—H13D	0.9800
C6—C7	1.4643 (16)	C13—H13F	0.9800

N2—N1—C2	113.34 (9)	C7—C8—H8	119.8
N2—N1—H1N	119.3 (11)	C8—C9—C10	121.78 (12)
C2—N1—H1N	127.0 (11)	C8—C9—H9	119.1
C4—N2—N1	103.78 (9)	C10—C9—H9	119.1
C5—N3—N4	119.69 (9)	C11—C10—C9	117.68 (12)
C5—N3—H3N	119.3 (11)	C11—C10—C13	121.46 (12)
N4—N3—H3N	120.9 (11)	C9—C10—C13	120.86 (12)
C6—N4—N3	114.64 (10)	C10—C11—C12	121.14 (12)
C2—C1—H1A	109.5	C10—C11—H11	119.4
C2—C1—H1B	109.5	C12—C11—H11	119.4
H1A—C1—H1B	109.5	C11—C12—C7	120.82 (11)
C2—C1—H1C	109.5	C11—C12—H12	119.6
H1A—C1—H1C	109.5	C7—C12—H12	119.6
H1B—C1—H1C	109.5	C10—C13—H13A	109.5
N1—C2—C3	106.12 (10)	C10—C13—H13B	109.5
N1—C2—C1	121.44 (10)	H13A—C13—H13B	109.5
C3—C2—C1	132.41 (11)	C10—C13—H13C	109.5
C2—C3—C4	104.82 (10)	H13A—C13—H13C	109.5
C2—C3—H3A	127.6	H13B—C13—H13C	109.5
C4—C3—H3A	127.6	C10—C13—H13E	109.5
N2—C4—C3	111.94 (10)	H13A—C13—H13E	141.1
N2—C4—C5	120.14 (10)	H13B—C13—H13E	56.3
C3—C4—C5	127.90 (10)	H13C—C13—H13E	56.3
O1—C5—N3	123.37 (11)	C10—C13—H13D	109.5
O1—C5—C4	122.23 (10)	H13A—C13—H13D	56.3
N3—C5—C4	114.40 (10)	H13B—C13—H13D	141.1
N4—C6—C7	122.21 (11)	H13C—C13—H13D	56.3
N4—C6—H6	118.9	H13E—C13—H13D	109.5
C7—C6—H6	118.9	C10—C13—H13F	109.5
C12—C7—C8	118.25 (11)	H13A—C13—H13F	56.3
C12—C7—C6	118.69 (11)	H13B—C13—H13F	56.3
C8—C7—C6	123.06 (11)	H13C—C13—H13F	141.1
C9—C8—C7	120.32 (12)	H13E—C13—H13F	109.5
C9—C8—H8	119.8	H13D—C13—H13F	109.5

C2—N1—N2—C4	0.65 (13)	C3—C4—C5—N3	178.69 (11)
C5—N3—N4—C6	−177.96 (10)	N3—N4—C6—C7	179.59 (10)
N2—N1—C2—C3	−0.43 (14)	N4—C6—C7—C12	−170.31 (11)
N2—N1—C2—C1	−178.88 (10)	N4—C6—C7—C8	10.09 (19)
N1—C2—C3—C4	0.03 (13)	C12—C7—C8—C9	0.41 (19)
C1—C2—C3—C4	178.23 (12)	C6—C7—C8—C9	−179.99 (11)
N1—N2—C4—C3	−0.62 (13)	C7—C8—C9—C10	0.2 (2)
N1—N2—C4—C5	−178.99 (10)	C8—C9—C10—C11	−0.47 (19)
C2—C3—C4—N2	0.38 (14)	C8—C9—C10—C13	179.18 (12)
C2—C3—C4—C5	178.60 (11)	C9—C10—C11—C12	0.15 (19)
N4—N3—C5—O1	−2.66 (17)	C13—C10—C11—C12	−179.50 (12)
N4—N3—C5—C4	177.13 (9)	C10—C11—C12—C7	0.45 (19)
N2—C4—C5—O1	176.57 (11)	C8—C7—C12—C11	−0.73 (18)
C3—C4—C5—O1	−1.52 (19)	C6—C7—C12—C11	179.65 (11)
N2—C4—C5—N3	−3.22 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.905 (18)	2.191 (18)	2.8655 (13)	130.8 (14)
N1—H1N···N4ⁱ	0.905 (18)	2.395 (18)	3.2419 (14)	155.9 (15)
N3—H3N···O1ⁱⁱ	0.885 (18)	2.232 (18)	2.9971 (13)	144.4 (15)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.905 (18)	2.191 (18)	2.8655 (13)	130.8 (14)
N1—H1N···N4ⁱ	0.905 (18)	2.395 (18)	3.2419 (14)	155.9 (15)
N3—H3N···O1ⁱⁱ	0.885 (18)	2.232 (18)	2.9971 (13)	144.4 (15)

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

Experimental details

Crystal data
Chemical formula	C₁₃H₁₄N₄O
M_r	242.28
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	150
a, b, c (Å)	6.3283 (1), 19.6204 (4), 10.1245 (2)
β (°)	105.746 (1)
V (Å³)	1209.92 (4)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.72
Crystal size (mm)	0.18 × 0.11 × 0.05

Data collection
Diffractometer	Bruker D8 VENTURE PHOTON 100 CMOS
Absorption correction	Multi-scan (SADABS; Bruker, 2016)
T_min, T_max	0.88, 0.96
No. of measured, independent and observed [I > 2σ(I)] reflections	13389, 2396, 2144
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.618

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.091, 1.05
No. of reflections	2396
No. of parameters	174
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.22

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 #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. (2015a). Acta Cryst. A71, 3–8. Web of Science 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. (2015b). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar

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