organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoIUCrDATA
ISSN: 2414-3146

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

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.

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

As a continuation of our studies of pyrazole carbohydrazides (Karrouchi et al., 2015[Karrouchi, K., Ansar, M., Radi, S., Saadi, M. & El Ammari, L. (2015). Acta Cryst. E71, o890-o891.]), we have studied the action of 4-bromo­benzaldehyde towards 5-phenyl-1H-pyrazole-3-carbohydrazide. This readily leads to the title compound (Fig. 1[link]) 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]
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[link] and Fig. 2[link]) with the chains stacking along the c axis direction (Fig. 3[link]). 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 DA 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]
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]
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[link]. 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
Mr 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)
V3) 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[Bruker (2016). APEX3, SAINT and SADABS. Bruker AXS, Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.74, 0.93
No. of measured, independent and observed [I > 2σ(I)] reflections 19026, 2958, 2704
Rint 0.040
(sin θ/λ)max−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
Δρmax, Δρmin (e Å−3) 0.63, −0.42
Computer programs: APEX3 and SAINT (Bruker, 2016[Bruker (2016). APEX3, SAINT and SADABS. Bruker AXS, Inc., Madison, Wisconsin, USA.]), SHELXT (Sheldrick, 2015a[Sheldrick, G. M. (2015a). Acta Cryst. A71, 3-8.]), SHELXL2014 (Sheldrick, 2015b[Sheldrick, G. M. (2015b). Acta Cryst. C71, 3-8.]), DIAMOND (Brandenburg & Putz, 2012[Brandenburg, K. & Putz, H. (2012). DIAMOND. Crystal Impact GbR, Bonn, Germany.]) and SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Structural data


Experimental top

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 top

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.

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
[Figure 1] Fig. 1. The title molecule with labeling scheme and 50% probability ellipsoids.
[Figure 2] Fig. 2. A portion of one chain viewed along the c axis with the N—H···O hydrogen bonds shown as dotted lines.
[Figure 3] 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
C17H13BrN4OF(000) = 744
Mr = 369.22Dx = 1.622 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54178 Å
a = 15.5151 (3) ÅCell parameters from 9982 reflections
b = 7.1752 (1) Åθ = 3.0–72.1°
c = 14.4593 (3) ŵ = 3.79 mm1
β = 110.072 (1)°T = 150 K
V = 1511.90 (5) Å3Plate, colourless
Z = 40.20 × 0.08 × 0.02 mm
Data collection top
Bruker D8 VENTURE PHOTON 100 CMOS
diffractometer
2958 independent reflections
Radiation source: INCOATEC IµS micro–focus source2704 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.040
Detector resolution: 10.4167 pixels mm-1θmax = 72.1°, θmin = 3.0°
ω scansh = 1919
Absorption correction: multi-scan
(SADABS; Bruker, 2016)
k = 88
Tmin = 0.74, Tmax = 0.93l = 1716
19026 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.030Hydrogen site location: mixed
wR(F2) = 0.076H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0406P)2 + 1.1336P]
where P = (Fo2 + 2Fc2)/3
2958 reflections(Δ/σ)max = 0.001
216 parametersΔρmax = 0.63 e Å3
0 restraintsΔρmin = 0.42 e Å3
Crystal data top
C17H13BrN4OV = 1511.90 (5) Å3
Mr = 369.22Z = 4
Monoclinic, P21/cCu Kα radiation
a = 15.5151 (3) ŵ = 3.79 mm1
b = 7.1752 (1) ÅT = 150 K
c = 14.4593 (3) Å0.20 × 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)
Tmin = 0.74, Tmax = 0.93Rint = 0.040
19026 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0300 restraints
wR(F2) = 0.076H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.63 e Å3
2958 reflectionsΔρmin = 0.42 e Å3
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
xyzUiso*/Ueq
Br10.08242 (2)1.44181 (3)0.40787 (2)0.03152 (10)
O10.55572 (10)0.7240 (2)0.39651 (12)0.0274 (3)
N10.56205 (12)0.1066 (2)0.36792 (13)0.0209 (3)
H1A0.548 (2)0.014 (4)0.372 (2)0.037 (7)*
N20.50212 (11)0.2396 (2)0.37161 (12)0.0207 (3)
N30.41822 (12)0.5828 (2)0.37237 (13)0.0208 (3)
H3A0.3856 (19)0.477 (4)0.3598 (19)0.029 (7)*
N40.37729 (12)0.7495 (2)0.37822 (12)0.0216 (3)
C10.72343 (14)0.0664 (3)0.36873 (14)0.0201 (4)
C20.81039 (14)0.1483 (3)0.40431 (15)0.0248 (4)
H20.81690.27140.43000.030*
C30.88713 (15)0.0518 (3)0.40256 (17)0.0300 (5)
H30.94590.10900.42710.036*
C40.87849 (15)0.1286 (3)0.36503 (16)0.0289 (5)
H40.93110.19480.36370.035*
C50.79246 (15)0.2107 (3)0.32966 (15)0.0254 (4)
H50.78630.33370.30390.030*
C60.71507 (14)0.1153 (3)0.33133 (15)0.0219 (4)
H60.65650.17330.30710.026*
C70.64455 (13)0.1770 (3)0.37096 (14)0.0196 (4)
C80.63687 (14)0.3686 (3)0.37568 (15)0.0208 (4)
H80.68210.45960.37810.025*
C90.54810 (14)0.3990 (3)0.37609 (15)0.0194 (4)
C100.50863 (14)0.5828 (3)0.38258 (14)0.0198 (4)
C110.28977 (14)0.7463 (3)0.35493 (15)0.0218 (4)
H110.25660.63440.33220.026*
C120.24174 (14)0.9165 (3)0.36375 (14)0.0207 (4)
C130.14574 (14)0.9207 (3)0.32523 (15)0.0226 (4)
H130.11290.81550.29100.027*
C140.09828 (14)1.0785 (3)0.33688 (15)0.0234 (4)
H140.03321.08240.31030.028*
C150.14737 (14)1.2290 (3)0.38761 (15)0.0223 (4)
C160.24238 (14)1.2301 (3)0.42531 (15)0.0234 (4)
H160.27461.33590.45960.028*
C170.28952 (14)1.0742 (3)0.41216 (15)0.0223 (4)
H170.35471.07420.43610.027*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.03319 (15)0.02154 (14)0.03802 (15)0.00873 (9)0.00988 (10)0.00237 (9)
O10.0251 (7)0.0134 (7)0.0448 (9)0.0016 (6)0.0134 (7)0.0016 (6)
N10.0225 (8)0.0126 (8)0.0281 (9)0.0014 (6)0.0093 (7)0.0000 (7)
N20.0210 (8)0.0128 (8)0.0276 (9)0.0022 (6)0.0074 (7)0.0008 (6)
N30.0209 (8)0.0136 (8)0.0283 (9)0.0006 (6)0.0092 (7)0.0029 (7)
N40.0251 (9)0.0160 (8)0.0238 (8)0.0044 (6)0.0084 (7)0.0005 (6)
C10.0222 (10)0.0191 (10)0.0199 (9)0.0035 (7)0.0084 (8)0.0012 (7)
C20.0264 (10)0.0211 (10)0.0264 (11)0.0006 (8)0.0082 (8)0.0053 (8)
C30.0214 (10)0.0364 (13)0.0319 (11)0.0007 (9)0.0088 (9)0.0039 (9)
C40.0273 (11)0.0324 (12)0.0294 (11)0.0088 (9)0.0127 (9)0.0007 (9)
C50.0320 (11)0.0218 (10)0.0247 (10)0.0056 (8)0.0128 (9)0.0006 (8)
C60.0267 (10)0.0183 (9)0.0217 (10)0.0008 (8)0.0097 (8)0.0009 (8)
C70.0216 (9)0.0166 (9)0.0208 (9)0.0018 (7)0.0077 (7)0.0002 (7)
C80.0230 (10)0.0136 (9)0.0271 (10)0.0000 (7)0.0103 (8)0.0011 (7)
C90.0227 (9)0.0127 (9)0.0227 (9)0.0007 (7)0.0076 (8)0.0000 (7)
C100.0214 (9)0.0163 (9)0.0221 (9)0.0012 (7)0.0079 (8)0.0009 (7)
C110.0235 (10)0.0188 (10)0.0234 (10)0.0002 (8)0.0085 (8)0.0009 (8)
C120.0231 (10)0.0200 (10)0.0206 (9)0.0032 (7)0.0096 (8)0.0024 (7)
C130.0216 (10)0.0202 (10)0.0264 (10)0.0028 (7)0.0086 (8)0.0024 (8)
C140.0202 (9)0.0248 (10)0.0258 (10)0.0020 (8)0.0086 (8)0.0014 (8)
C150.0265 (10)0.0189 (10)0.0224 (10)0.0033 (8)0.0094 (8)0.0024 (8)
C160.0258 (10)0.0197 (10)0.0228 (10)0.0012 (8)0.0059 (8)0.0005 (8)
C170.0209 (9)0.0235 (10)0.0213 (9)0.0012 (8)0.0055 (8)0.0010 (8)
Geometric parameters (Å, º) top
Br1—C151.907 (2)C5—C61.389 (3)
O1—C101.225 (2)C5—H50.9500
N1—N21.346 (2)C6—H60.9500
N1—C71.362 (3)C7—C81.384 (3)
N1—H1A0.90 (3)C8—C91.397 (3)
N2—C91.338 (3)C8—H80.9500
N3—C101.359 (3)C9—C101.470 (3)
N3—N41.370 (2)C11—C121.459 (3)
N3—H3A0.90 (3)C11—H110.9500
N4—C111.282 (3)C12—C131.400 (3)
C1—C21.398 (3)C12—C171.401 (3)
C1—C61.400 (3)C13—C141.392 (3)
C1—C71.468 (3)C13—H130.9500
C2—C31.385 (3)C14—C151.379 (3)
C2—H20.9500C14—H140.9500
C3—C41.392 (3)C15—C161.385 (3)
C3—H30.9500C16—C171.385 (3)
C4—C51.386 (3)C16—H160.9500
C4—H40.9500C17—H170.9500
N2—N1—C7112.98 (16)C7—C8—H8127.5
N2—N1—H1A119.1 (19)C9—C8—H8127.5
C7—N1—H1A127.4 (19)N2—C9—C8112.11 (17)
C9—N2—N1104.11 (15)N2—C9—C10122.89 (18)
C10—N3—N4118.45 (16)C8—C9—C10125.00 (18)
C10—N3—H3A120.8 (17)O1—C10—N3123.57 (18)
N4—N3—H3A120.7 (17)O1—C10—C9120.95 (18)
C11—N4—N3116.10 (17)N3—C10—C9115.48 (17)
C2—C1—C6118.90 (18)N4—C11—C12119.27 (19)
C2—C1—C7118.12 (18)N4—C11—H11120.4
C6—C1—C7122.97 (19)C12—C11—H11120.4
C3—C2—C1120.7 (2)C13—C12—C17119.30 (18)
C3—C2—H2119.6C13—C12—C11119.27 (18)
C1—C2—H2119.7C17—C12—C11121.41 (18)
C2—C3—C4120.2 (2)C14—C13—C12120.29 (19)
C2—C3—H3119.9C14—C13—H13119.9
C4—C3—H3119.9C12—C13—H13119.9
C5—C4—C3119.4 (2)C15—C14—C13118.87 (19)
C5—C4—H4120.3C15—C14—H14120.6
C3—C4—H4120.3C13—C14—H14120.6
C4—C5—C6120.8 (2)C14—C15—C16122.17 (19)
C4—C5—H5119.6C14—C15—Br1118.98 (15)
C6—C5—H5119.6C16—C15—Br1118.84 (16)
C5—C6—C1119.9 (2)C17—C16—C15118.86 (19)
C5—C6—H6120.0C17—C16—H16120.6
C1—C6—H6120.0C15—C16—H16120.6
N1—C7—C8105.89 (17)C16—C17—C12120.46 (19)
N1—C7—C1125.45 (18)C16—C17—H17119.8
C8—C7—C1128.65 (19)C12—C17—H17119.8
C7—C8—C9104.91 (17)
C7—N1—N2—C90.6 (2)C7—C8—C9—C10178.65 (19)
C10—N3—N4—C11170.82 (18)N4—N3—C10—O10.2 (3)
C6—C1—C2—C30.1 (3)N4—N3—C10—C9179.64 (17)
C7—C1—C2—C3178.9 (2)N2—C9—C10—O1172.58 (19)
C1—C2—C3—C40.1 (3)C8—C9—C10—O16.2 (3)
C2—C3—C4—C50.1 (3)N2—C9—C10—N37.3 (3)
C3—C4—C5—C60.1 (3)C8—C9—C10—N3173.97 (19)
C4—C5—C6—C10.3 (3)N3—N4—C11—C12177.16 (17)
C2—C1—C6—C50.3 (3)N4—C11—C12—C13170.84 (19)
C7—C1—C6—C5178.70 (18)N4—C11—C12—C1710.8 (3)
N2—N1—C7—C80.8 (2)C17—C12—C13—C141.4 (3)
N2—N1—C7—C1179.63 (18)C11—C12—C13—C14176.94 (18)
C2—C1—C7—N1159.20 (19)C12—C13—C14—C150.6 (3)
C6—C1—C7—N121.8 (3)C13—C14—C15—C161.6 (3)
C2—C1—C7—C821.3 (3)C13—C14—C15—Br1177.73 (15)
C6—C1—C7—C8157.7 (2)C14—C15—C16—C170.5 (3)
N1—C7—C8—C90.6 (2)Br1—C15—C16—C17178.84 (15)
C1—C7—C8—C9179.86 (19)C15—C16—C17—C121.6 (3)
N1—N2—C9—C80.2 (2)C13—C12—C17—C162.6 (3)
N1—N2—C9—C10179.13 (18)C11—C12—C17—C16175.78 (18)
C7—C8—C9—N20.2 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···N20.90 (3)2.45 (3)2.787 (2)103 (2)
N1—H1A···O1i0.90 (3)1.91 (3)2.783 (2)163 (3)
C6—H6···O1i0.952.463.151 (3)130
Symmetry code: (i) x, y1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···N20.90 (3)2.45 (3)2.787 (2)103 (2)
N1—H1A···O1i0.90 (3)1.91 (3)2.783 (2)163 (3)
C6—H6···O1i0.952.463.151 (3)130
Symmetry code: (i) x, y1, z.

Experimental details

Crystal data
Chemical formulaC17H13BrN4O
Mr369.22
Crystal system, space groupMonoclinic, P21/c
Temperature (K)150
a, b, c (Å)15.5151 (3), 7.1752 (1), 14.4593 (3)
β (°) 110.072 (1)
V3)1511.90 (5)
Z4
Radiation typeCu Kα
µ (mm1)3.79
Crystal size (mm)0.20 × 0.08 × 0.02
Data collection
DiffractometerBruker D8 VENTURE PHOTON 100 CMOS
Absorption correctionMulti-scan
(SADABS; Bruker, 2016)
Tmin, Tmax0.74, 0.93
No. of measured, independent and
observed [I > 2σ(I)] reflections
19026, 2958, 2704
Rint0.040
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.030, 0.076, 1.04
No. of reflections2958
No. of parameters216
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)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

First citationBrandenburg, K. & Putz, H. (2012). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
First citationBruker (2016). APEX3, SAINT and SADABS. Bruker AXS, Inc., Madison, Wisconsin, USA.  Google Scholar
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