Crystal structure of 5-(4-meth­oxy­phen­yl)-3-(4-methyl­phen­yl)-4,5-di­hydro-1H-pyrazole-1-carbaldehyde

Adam, F.; Samshuddin, S.; Shruthi; Narayana, B.; Ameram, N.

doi:10.1107/S2056989015023658

organic compounds

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ISSN: 2056-9890

Volume 71| Part 12| December 2015| Pages o1093-o1094

https://doi.org/10.1107/S2056989015023658

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Crystal structure of 5-(4-methoxyphenyl)-3-(4-methylphenyl)-4,5-dihydro-1H-pyrazole-1-carbaldehyde

Farook Adam,^a ^* Seranthimata Samshuddin,^b Shruthi,^b Badiadka Narayana ^c and Nadiah Ameram ^a

^aSchool of Chemical Sciences, Universiti Sains Malaysia, 18000 Pulau Pinang, Malaysia, ^bDepartment of P.G. Studies in Chemistry, Alva's College, Moodbidri, Karnataka 574 227, India, and ^cDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, Karnataka 574 227, India
^*Correspondence e-mail: farook@usm.my

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 8 December 2015; accepted 9 December 2015; online 31 December 2015)

In the title compound, C₁₈H₁₈N₂O₂, the pyrazole ring has a twisted conformation on the CH—CH₂ bond. The tolyl ring and the 4-methoxyphenyl ring are inclined to the mean plane of the pyrazole ring by 4.40 (9) and 86.22 (9)°, respectively, while the two aromatic rings are inclined to one another by 88.75 (9)°. In the crystal, molecules are linked via bifurcated C—H⋯(O,O) hydrogen bonds and C—H⋯π interactions, forming sheets lying parallel to the ab plane.

Keywords: crystal structure; pyrazole; hydrogen bonding.

CCDC reference: 1441491

1. Related literature

For examples of the numerous pharmacological activities of pyrazoles, see: Samshuddin et al. (2012 ); Sarojini et al. (2010 ). For the use of 1,3,5-triaryl-2-pyrazolines as scintillation solutes, see: Wiley et al. (1958 ); and as fluorescent agents, see: Lu et al. (1999 ). For the crystal structures of pyrazoline-derived chalcones, see: Jasinski et al. (2012 ); Baktır et al. (2011 ).

2. Experimental

2.1. Crystal data

C₁₈H₁₈N₂O₂
M_r = 294.34
Monoclinic, C c
a = 12.0839 (9) Å
b = 6.4197 (5) Å
c = 19.7427 (18) Å
β = 104.8264 (12)°
V = 1480.5 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.41 × 0.23 × 0.11 mm

2.2. Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2010 ) T_min = 0.919, T_max = 0.965
14663 measured reflections
4301 independent reflections
4070 reflections with I > 2σ(I)
R_int = 0.023

2.3. Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.097
S = 1.05
4301 reflections
201 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯O2ⁱ	0.95	2.39	3.207 (2)	144
C14—H14A⋯O2ⁱⁱ	0.95	2.57	3.477 (2)	160
C15—H15A⋯Cg2ⁱⁱⁱ	0.95	2.78	3.661 (2)	154
Symmetry codes: (i) x, y+1, z; (ii) $[x+{\script{1\over 2}}, y+{\script{3\over 2}}, z]$ ; (iii) $[x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ .

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick 2008 ); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ); molecular graphics: SHELXTL (Sheldrick 2008); software used to prepare material for publication: SHELXTL.

Supporting information

CCDC reference: 1441491

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: https://doi.org/10.1107/S2056989015023658/su5259sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015023658/su5259Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015023658/su5259Isup3.cml

checkCIF report

Comment top

Pyrazoline derivatives exhibit numerous pharmacological activities including antioxidant, antiamoebic, anti-inflammatory, analgesic, antimicrobial, antidepressant and anticancer activities (Sarojini et al., 2010; Samshuddin et al., 2012). Many 1,3,5-triaryl-2-pyrazolines have also been used as scintillation solutes (Wiley et al., 1958) and as fluorescent agents (Lu et al., 1999).

The crystal structures of some pyrazolines containing an N-alkyl chain, viz. 3,5-bis(4-fluorophenyl)-4,5-dihydro-1H-pyrazole-1 carbaldehyde (Baktır et al., 2011), 3,5-bis(4-fluorophenyl)-4,5-dihydro- 1H-pyrazole-1-carboxamide and 3,5-bis(4-fluorophenyl)-4,5-dihydro- 1H-pyrazole-1-carbothioamide (Jasinski et al., 2012) have been reported. In view of the importance of pyrazolines, the title compound was synthesized and we report herein on its crystal structure.

The molecular structure of the title compound is illustrated in Fig. 1. The pyrazole ring has a twisted conformation on bond C7—C8. The toluyl ring and the 4-methoxyphenyl ring are inclined to the mean plane of the pyrazole ring by 4.40 (9) and 86.22 (9) °, respectively. The two aromatic rings are inclined to one another by 88.75 (9) °.

In the crystal, molecules are linked via C—H···O hydrogen bonds and C—H···π interactions forming sheets lying parallel to the ab plane (Table 1 and Fig. 2).

Synthesis and crystallization top

A mixture of (2E)-3-(4-methoxyphenyl)-1-(4-methylphenyl)prop-2-en-1-one (2.52 g, 0.01 mol) and hydrazine hydrate (1 ml) in 30 ml formic acid was refluxed for 6 h. The reaction mixture was cooled and poured into 50 ml ice-cold water. The precipitate was collected by filtration and purified by recrystallization from ethanol. Single crystals were grown from toluene by slow evaporation of the solvent (yield: 75 %; m.p. 479-482 K).

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 2. The hydrogen atoms were fixed geometrically (C—H = 0.95–1.00 Å) and allowed to ride on their parent atoms with U_iso(H) = 1.5U_eq(C-methyl) and 1.2U_eq(C) for other H atoms.

Related literature top

For examples of the numerous pharmacological activities of pyrazoles, see: Samshuddin et al. (2012); Sarojini et al. (2010). For the use of 1,3,5-triaryl-2-pyrazolines as scintillation solutes, see: Wiley et al. (1958); and as fluorescent agents, see: Lu et al. (1999). For the crystal structures of pyrazoline-derived chalcones, see: Jasinski et al. (2012); Baktır et al. (2011).

Structure description top

In the crystal, molecules are linked via C—H···O hydrogen bonds and C—H···π interactions forming sheets lying parallel to the ab plane (Table 1 and Fig. 2).

For examples of the numerous pharmacological activities of pyrazoles, see: Samshuddin et al. (2012); Sarojini et al. (2010). For the use of 1,3,5-triaryl-2-pyrazolines as scintillation solutes, see: Wiley et al. (1958); and as fluorescent agents, see: Lu et al. (1999). For the crystal structures of pyrazoline-derived chalcones, see: Jasinski et al. (2012); Baktır et al. (2011).

Synthesis and crystallization top

Refinement details top

Computing details top

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT (Bruker, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick 2008); software used to prepare material for publication: SHELXTL (Sheldrick 2008).

Figures top

	Fig. 1. A view of the molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 50 % probability level.
	Fig. 2. A view along the ab axis of the crystal packing of the title compound. Hydrogen bonds are shown as dashed lines (see Table 1).

5-(4-Methoxyphenyl)-3-(4-methylphenyl)-4,5-dihydro-1H-pyrazole-1-carbaldehyde top

Crystal data top

C₁₈H₁₈N₂O₂	F(000) = 624
M_r = 294.34	D_x = 1.321 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
a = 12.0839 (9) Å	Cell parameters from 6705 reflections
b = 6.4197 (5) Å	θ = 3.5–30.2°
c = 19.7427 (18) Å	µ = 0.09 mm⁻¹
β = 104.8264 (12)°	T = 100 K
V = 1480.5 (2) Å³	Block, colourless
Z = 4	0.41 × 0.23 × 0.11 mm

Data collection top

Bruker APEXII CCD diffractometer	4070 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.023
Absorption correction: multi-scan (SADABS; Bruker, 2010)	θ_max = 30.2°, θ_min = 2.1°
T_min = 0.919, T_max = 0.965	h = −17→17
14663 measured reflections	k = −9→9
4301 independent reflections	l = −27→27

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.097	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0604P)² + 0.3156P] where P = (F_o² + 2F_c²)/3
4301 reflections	(Δ/σ)_max < 0.001
201 parameters	Δρ_max = 0.28 e Å⁻³
2 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₁₈H₁₈N₂O₂	V = 1480.5 (2) Å³
M_r = 294.34	Z = 4
Monoclinic, Cc	Mo Kα radiation
a = 12.0839 (9) Å	µ = 0.09 mm⁻¹
b = 6.4197 (5) Å	T = 100 K
c = 19.7427 (18) Å	0.41 × 0.23 × 0.11 mm
β = 104.8264 (12)°

Data collection top

Bruker APEXII CCD diffractometer	4301 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2010)	4070 reflections with I > 2σ(I)
T_min = 0.919, T_max = 0.965	R_int = 0.023
14663 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	2 restraints
wR(F²) = 0.097	H-atom parameters constrained
S = 1.05	Δρ_max = 0.28 e Å⁻³
4301 reflections	Δρ_min = −0.19 e Å⁻³
201 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.

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

	x	y	z	U_iso*/U_eq
O1	0.20348 (12)	0.4331 (2)	0.35129 (8)	0.0248 (3)
O2	0.54286 (12)	−0.1313 (2)	0.56436 (8)	0.0229 (3)
N1	0.64240 (13)	0.1726 (2)	0.58103 (8)	0.0167 (3)
N2	0.68881 (12)	0.3318 (2)	0.62747 (8)	0.0164 (3)
C1	0.49214 (15)	0.4726 (3)	0.46209 (9)	0.0179 (3)
H1A	0.5393	0.5782	0.4884	0.022*
C2	0.38193 (16)	0.5207 (3)	0.42425 (9)	0.0189 (3)
H2A	0.3543	0.6591	0.4246	0.023*
C3	0.31110 (15)	0.3672 (3)	0.38556 (9)	0.0186 (3)
C4	0.35270 (16)	0.1650 (3)	0.38360 (9)	0.0199 (4)
H4A	0.3059	0.0603	0.3566	0.024*
C5	0.46443 (15)	0.1188 (3)	0.42203 (9)	0.0187 (3)
H5A	0.4930	−0.0187	0.4208	0.022*
C6	0.53452 (15)	0.2698 (3)	0.46190 (9)	0.0168 (3)
C7	0.65113 (15)	0.2100 (3)	0.50826 (9)	0.0171 (3)
H7A	0.6815	0.0838	0.4894	0.021*
C8	0.74108 (15)	0.3870 (3)	0.52205 (10)	0.0191 (3)
H8A	0.8174	0.3345	0.5204	0.023*
H8B	0.7182	0.5012	0.4876	0.023*
C9	0.74102 (14)	0.4580 (3)	0.59498 (9)	0.0153 (3)
C10	0.79896 (14)	0.6448 (2)	0.62925 (9)	0.0151 (3)
C11	0.79596 (15)	0.6957 (3)	0.69768 (9)	0.0178 (3)
H11A	0.7553	0.6091	0.7220	0.021*
C12	0.85202 (15)	0.8719 (3)	0.73026 (10)	0.0191 (3)
H12A	0.8487	0.9049	0.7766	0.023*
C13	0.91324 (14)	1.0015 (3)	0.69604 (10)	0.0181 (3)
C14	0.91505 (14)	0.9520 (3)	0.62759 (9)	0.0180 (3)
H14A	0.9554	1.0394	0.6033	0.022*
C15	0.85852 (14)	0.7760 (3)	0.59414 (9)	0.0171 (3)
H15A	0.8604	0.7451	0.5474	0.020*
C16	0.12863 (18)	0.2852 (4)	0.30873 (12)	0.0300 (4)
H16A	0.0551	0.3519	0.2871	0.045*
H16B	0.1163	0.1682	0.3378	0.045*
H16C	0.1631	0.2340	0.2720	0.045*
C17	0.58798 (15)	0.0120 (3)	0.60245 (10)	0.0191 (3)
H17A	0.5844	0.0099	0.6500	0.023*
C18	0.97566 (17)	1.1908 (3)	0.73207 (11)	0.0236 (4)
H18A	1.0484	1.2064	0.7192	0.035*
H18B	0.9906	1.1740	0.7829	0.035*
H18C	0.9285	1.3151	0.7174	0.035*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0198 (6)	0.0266 (7)	0.0257 (7)	0.0009 (5)	0.0014 (5)	−0.0011 (5)
O2	0.0226 (6)	0.0158 (6)	0.0292 (7)	−0.0031 (5)	0.0044 (5)	−0.0006 (5)
N1	0.0171 (7)	0.0156 (6)	0.0168 (7)	−0.0029 (5)	0.0032 (5)	−0.0016 (5)
N2	0.0152 (6)	0.0153 (6)	0.0171 (7)	−0.0010 (5)	0.0015 (5)	−0.0010 (5)
C1	0.0205 (8)	0.0170 (7)	0.0171 (8)	−0.0034 (6)	0.0063 (6)	−0.0027 (6)
C2	0.0227 (8)	0.0171 (7)	0.0177 (8)	0.0006 (6)	0.0068 (6)	−0.0008 (6)
C3	0.0182 (8)	0.0226 (8)	0.0154 (7)	−0.0009 (6)	0.0050 (6)	0.0007 (6)
C4	0.0205 (9)	0.0202 (8)	0.0177 (8)	−0.0050 (6)	0.0028 (7)	−0.0028 (6)
C5	0.0213 (8)	0.0164 (7)	0.0185 (8)	−0.0016 (6)	0.0051 (7)	−0.0024 (6)
C6	0.0183 (8)	0.0171 (7)	0.0154 (8)	−0.0030 (6)	0.0051 (6)	−0.0022 (6)
C7	0.0158 (7)	0.0180 (8)	0.0176 (8)	−0.0022 (6)	0.0045 (6)	−0.0028 (6)
C8	0.0166 (7)	0.0212 (8)	0.0202 (8)	−0.0049 (6)	0.0063 (6)	−0.0034 (6)
C9	0.0131 (7)	0.0156 (7)	0.0163 (8)	−0.0002 (6)	0.0022 (6)	−0.0016 (6)
C10	0.0120 (7)	0.0139 (7)	0.0182 (8)	0.0003 (5)	0.0019 (6)	−0.0005 (6)
C11	0.0187 (8)	0.0173 (7)	0.0180 (8)	−0.0017 (6)	0.0058 (6)	0.0006 (6)
C12	0.0193 (8)	0.0186 (8)	0.0189 (8)	−0.0005 (6)	0.0040 (7)	−0.0018 (6)
C13	0.0163 (8)	0.0148 (7)	0.0216 (8)	−0.0001 (6)	0.0017 (6)	−0.0016 (6)
C14	0.0164 (8)	0.0163 (7)	0.0217 (8)	−0.0016 (6)	0.0055 (7)	0.0005 (6)
C15	0.0165 (7)	0.0173 (7)	0.0180 (8)	−0.0009 (6)	0.0057 (6)	−0.0001 (6)
C16	0.0212 (9)	0.0341 (10)	0.0294 (11)	−0.0026 (8)	−0.0031 (8)	−0.0018 (8)
C17	0.0172 (8)	0.0163 (7)	0.0233 (9)	0.0007 (6)	0.0043 (7)	0.0036 (6)
C18	0.0242 (9)	0.0168 (8)	0.0280 (10)	−0.0041 (6)	0.0035 (7)	−0.0046 (7)

Geometric parameters (Å, º) top

O1—C3	1.370 (2)	C8—H8A	0.9900
O1—C16	1.427 (2)	C8—H8B	0.9900
O2—C17	1.225 (2)	C9—C10	1.464 (2)
N1—C17	1.348 (2)	C10—C11	1.399 (2)
N1—N2	1.3916 (19)	C10—C15	1.401 (2)
N1—C7	1.487 (2)	C11—C12	1.389 (2)
N2—C9	1.294 (2)	C11—H11A	0.9500
C1—C2	1.385 (3)	C12—C13	1.397 (2)
C1—C6	1.400 (2)	C12—H12A	0.9500
C1—H1A	0.9500	C13—C14	1.394 (3)
C2—C3	1.397 (2)	C13—C18	1.509 (2)
C2—H2A	0.9500	C14—C15	1.396 (2)
C3—C4	1.396 (2)	C14—H14A	0.9500
C4—C5	1.401 (3)	C15—H15A	0.9500
C4—H4A	0.9500	C16—H16A	0.9800
C5—C6	1.391 (2)	C16—H16B	0.9800
C5—H5A	0.9500	C16—H16C	0.9800
C6—C7	1.520 (2)	C17—H17A	0.9500
C7—C8	1.547 (2)	C18—H18A	0.9800
C7—H7A	1.0000	C18—H18B	0.9800
C8—C9	1.510 (2)	C18—H18C	0.9800

C3—O1—C16	117.61 (16)	N2—C9—C8	113.76 (14)
C17—N1—N2	120.11 (15)	C10—C9—C8	124.81 (15)
C17—N1—C7	126.02 (15)	C11—C10—C15	118.75 (15)
N2—N1—C7	113.67 (13)	C11—C10—C9	120.65 (15)
C9—N2—N1	107.38 (14)	C15—C10—C9	120.60 (16)
C2—C1—C6	120.53 (16)	C12—C11—C10	120.46 (16)
C2—C1—H1A	119.7	C12—C11—H11A	119.8
C6—C1—H1A	119.7	C10—C11—H11A	119.8
C1—C2—C3	120.51 (16)	C11—C12—C13	121.13 (16)
C1—C2—H2A	119.7	C11—C12—H12A	119.4
C3—C2—H2A	119.7	C13—C12—H12A	119.4
O1—C3—C4	125.21 (16)	C14—C13—C12	118.34 (16)
O1—C3—C2	115.02 (16)	C14—C13—C18	120.72 (16)
C4—C3—C2	119.76 (16)	C12—C13—C18	120.95 (17)
C3—C4—C5	119.09 (16)	C13—C14—C15	121.08 (16)
C3—C4—H4A	120.5	C13—C14—H14A	119.5
C5—C4—H4A	120.5	C15—C14—H14A	119.5
C6—C5—C4	121.44 (16)	C14—C15—C10	120.23 (16)
C6—C5—H5A	119.3	C14—C15—H15A	119.9
C4—C5—H5A	119.3	C10—C15—H15A	119.9
C5—C6—C1	118.65 (16)	O1—C16—H16A	109.5
C5—C6—C7	120.08 (15)	O1—C16—H16B	109.5
C1—C6—C7	121.11 (15)	H16A—C16—H16B	109.5
N1—C7—C6	109.79 (14)	O1—C16—H16C	109.5
N1—C7—C8	99.73 (14)	H16A—C16—H16C	109.5
C6—C7—C8	114.96 (15)	H16B—C16—H16C	109.5
N1—C7—H7A	110.6	O2—C17—N1	123.94 (18)
C6—C7—H7A	110.6	O2—C17—H17A	118.0
C8—C7—H7A	110.6	N1—C17—H17A	118.0
C9—C8—C7	102.57 (14)	C13—C18—H18A	109.5
C9—C8—H8A	111.3	C13—C18—H18B	109.5
C7—C8—H8A	111.3	H18A—C18—H18B	109.5
C9—C8—H8B	111.3	C13—C18—H18C	109.5
C7—C8—H8B	111.3	H18A—C18—H18C	109.5
H8A—C8—H8B	109.2	H18B—C18—H18C	109.5
N2—C9—C10	121.34 (15)

C17—N1—N2—C9	176.47 (16)	N1—C7—C8—C9	−15.61 (17)
C7—N1—N2—C9	−8.36 (18)	C6—C7—C8—C9	101.70 (17)
C6—C1—C2—C3	0.3 (3)	N1—N2—C9—C10	179.55 (14)
C16—O1—C3—C4	−1.7 (3)	N1—N2—C9—C8	−3.61 (19)
C16—O1—C3—C2	177.67 (17)	C7—C8—C9—N2	13.1 (2)
C1—C2—C3—O1	179.00 (16)	C7—C8—C9—C10	−170.18 (15)
C1—C2—C3—C4	−1.6 (3)	N2—C9—C10—C11	−2.2 (2)
O1—C3—C4—C5	−179.20 (17)	C8—C9—C10—C11	−178.69 (17)
C2—C3—C4—C5	1.5 (3)	N2—C9—C10—C15	177.74 (16)
C3—C4—C5—C6	−0.1 (3)	C8—C9—C10—C15	1.3 (2)
C4—C5—C6—C1	−1.2 (3)	C15—C10—C11—C12	−0.6 (2)
C4—C5—C6—C7	174.34 (16)	C9—C10—C11—C12	179.34 (16)
C2—C1—C6—C5	1.1 (3)	C10—C11—C12—C13	−0.5 (3)
C2—C1—C6—C7	−174.42 (16)	C11—C12—C13—C14	1.2 (3)
C17—N1—C7—C6	69.3 (2)	C11—C12—C13—C18	−178.97 (17)
N2—N1—C7—C6	−105.52 (16)	C12—C13—C14—C15	−0.8 (3)
C17—N1—C7—C8	−169.58 (16)	C18—C13—C14—C15	179.34 (16)
N2—N1—C7—C8	15.59 (18)	C13—C14—C15—C10	−0.3 (3)
C5—C6—C7—N1	−95.70 (18)	C11—C10—C15—C14	1.0 (2)
C1—C6—C7—N1	79.7 (2)	C9—C10—C15—C14	−178.97 (15)
C5—C6—C7—C8	152.86 (16)	N2—N1—C17—O2	178.37 (16)
C1—C6—C7—C8	−31.7 (2)	C7—N1—C17—O2	3.8 (3)

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O2ⁱ	0.95	2.39	3.207 (2)	144
C14—H14A···O2ⁱⁱ	0.95	2.57	3.477 (2)	160
C15—H15A···Cg2ⁱⁱⁱ	0.95	2.78	3.661 (2)	154

Symmetry codes: (i) x, y+1, z; (ii) x+1/2, y+3/2, z; (iii) x+1/2, y+1/2, z.

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O2ⁱ	0.95	2.39	3.207 (2)	144
C14—H14A···O2ⁱⁱ	0.95	2.57	3.477 (2)	160
C15—H15A···Cg2ⁱⁱⁱ	0.95	2.78	3.661 (2)	154

Symmetry codes: (i) x, y+1, z; (ii) x+1/2, y+3/2, z; (iii) x+1/2, y+1/2, z.

Acknowledgements

SS thanks Alva's Education Foundation, Moodbidri, for providing research facilities. FA is grateful for USM research grants 1001/PKIMIA/846017 and 1001/PKIMIA/811269, which partially supported this research.

References

Baktır, Z., Akkurt, M., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2011). Acta Cryst. E67, o1292–o1293. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bruker (2010). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Jasinski, J. P., Golen, J. A., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2012). Crystals, 2, 1108–1115. Web of Science CrossRef CAS Google Scholar
Lu, Z.-Y., Zhu, W.-G., Jiang, Q. & Xie, M.-G. (1999). Chin. Chem. Lett. 10, 679–682. CAS Google Scholar
Samshuddin, S., Narayana, B., Sarojini, B. K., Khan, M. T. H., Yathirajan, H. S., Raj, C. G. D. & Raghavendra, R. (2012). Med. Chem. Res. 21, 2012–2022. Web of Science CSD CrossRef CAS Google Scholar
Sarojini, B. K., Vidyagayatri, M., Darshanraj, C. G., Bharath, B. R. & Manjunatha, H. (2010). Lett. Drug. Des. Discov. 7, 214–224. CrossRef Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Wiley, R. H., Jarboe, C. H., Hayes, F. N., Hansbury, E., Nielsen, J. T., Callahan, P. X. & Sellars, M. (1958). J. Org. Chem. 23, 732–738. CrossRef CAS Web of Science Google Scholar

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Volume 71| Part 12| December 2015| Pages o1093-o1094

https://doi.org/10.1107/S2056989015023658

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

Crystal structure of 5-(4-meth­­oxy­phen­yl)-3-(4-methyl­phen­yl)-4,5-di­hydro-1H-pyrazole-1-carbaldehyde

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of 5-(4-methoxyphenyl)-3-(4-methylphenyl)-4,5-dihydro-1H-pyrazole-1-carbaldehyde