Crystal structure of 3-methyl-1-phenyl-5-(1H-pyrrol-1-yl)-1H-pyrazole-4-carbaldehyde

Mague, J.T.; Mohamed, S.K.; Akkurt, M.; El-Emary, T.I.; Albayati, M.R.

doi:10.1107/S1600536814020984

organic compounds

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ISSN: 2056-9890

Volume 70| Part 10| October 2014| Pages o1131-o1132

doi:10.1107/S1600536814020984

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Crystal structure of 3-methyl-1-phenyl-5-(1H-pyrrol-1-yl)-1H-pyrazole-4-carbaldehyde

Joel T. Mague,^a Shaaban K. Mohamed,^b,^c Mehmet Akkurt,^d Talaat I. El-Emary ^e and Mustafa R. Albayati ^f ^*

^aDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA, ^bChemistry and Environmental Division, Manchester Metropolitan University, Manchester, M1 5GD, England, ^cChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, ^dDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^eDepartment of Chemistry, Faculty of Science, Assiut University, 71515 Assiut, Egypt, and ^fKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
^*Correspondence e-mail: shaabankamel@yahoo.com

Edited by J. Simpson, University of Otago, New Zealand (Received 19 September 2014; accepted 20 September 2014; online 27 September 2014)

In the title compound, C₁₅H₁₃N₃O, the pyrrolyl and phenyl rings make dihedral angles of 58.99 (5) and 34.95 (5)°, respectively, with the central pyrazole ring. In the crystal, weak, pairwise C—H⋯O interactions across centers of symmetry form dimers, which are further associated into corrugated sheets running approximately parallel to (100) via weak C—H⋯N interactions.

Keywords: crystal structure; pyrazole ring; pyrrolyl ring; dimers.

CCDC reference: 1025251

1. Related literature

For the biological activity of pyrazoline-containing compounds see: Nauduri & Reddy (1998 ); Korgaokar et al. (1996 ); Taylor & Patel (1992 ); Ozdemir et al. (2007 ); Ruhoğlu et al. (2005 ); Palaska et al. (2001 ); Rajendra Prasad et al. (2005 ); Udupi et al. (1998 ). For synthetic and industrial applications of pyrazolo[3,4-b]pyrazines see: Rangnekar & Dhamnaskar (1990 ); Kopp et al. (2001 ); Farghaly & El-Kashef (2005 ).

2. Experimental

2.1. Crystal data

C₁₅H₁₃N₃O
M_r = 251.28
Monoclinic, P 2₁ /c
a = 9.5807 (8) Å
b = 15.1720 (13) Å
c = 8.7370 (8) Å
β = 93.6180 (11)°
V = 1267.46 (19) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 150 K
0.29 × 0.17 × 0.04 mm

2.2. Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2014 ) T_min = 0.98, T_max = 1.00
26282 measured reflections
3321 independent reflections
2527 reflections with I > 2σ(I)
R_int = 0.053

2.3. Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.114
S = 1.07
3321 reflections
173 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15⋯N1ⁱ	0.95	2.48	3.3931 (17)	161
C12—H12⋯O1ⁱⁱ	0.95	2.52	3.4255 (17)	159
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) -x+1, -y+1, -z+2.

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT; program(s) used to solve structure: SHELXT (Bruker, 2014); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2008 ); molecular graphics: DIAMOND (Brandenburg & Putz, 2012 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

CCDC reference: 1025251

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814020984/sj5428sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814020984/sj5428Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814020984/sj5428Isup3.cml

checkCIF report

Comment top

Pyrazolines and substituted pyrazolines exhibit a variety of biological activities displaying anti-bacterial (Nauduri & Reddy, 1998), anti-fungal (Korgaokar et al., 1996), anti-tumor (Taylor & Patel, 1992), anticonvulsant (Ozdemir et al., 2007; Ruhoğlu et al., 2005), anti-depressant (Palaska et al., 2001; Rajendra Prasad et al., 2005) and anti-inflammatory (Udupi et al., 1998) properties. Moreover, pyrazolo[3,4-b]pyrazines are also used as fluorescent and disperse dyes in dye chemistry (Rangnekar & Dhamnaskar, 1990; Kopp et al., 2001). In addition the title compound and its analogs have proved to be versatile compounds for use in the synthesis of several heterocycles (Farghaly & El-Kashef, 2005). Based on these findings and as part of our on-going study of the synthesis of bio-heterocyclic molecules, we report in this study the crystal structure of the title compound.

In the title compound (Fig. 1), the central pyrazole ring makes dihedral angles of 58.99 (5) and 34.95 (5)°, respectively, with the the pyrrolyl and phenyl rings. Weak, pairwise C12—H12···O1 interactions across centers of symmetry form dimers which are further associated into corrugated sheets running approximately parallel to (100) via weak C15—H15···N1 interactions (Table 1, Fig. 2 and Fig. 3).

Related literature top

For the biological activity of pyrazoline-containing compounds see: Nauduri & Reddy (1998); Korgaokar et al. (1996); Taylor & Patel (1992); Ozdemir et al. (2007); Ruhoğlu et al. (2005); Palaska et al. (2001); Rajendra Prasad et al. (2005); Udupi et al. (1998). For synthetic and industrial applications of pyrazolo[3,4-b]pyrazines see: Rangnekar & Dhamnaskar (1990); Kopp et al. (2001); Farghaly & El-Kashef (2005).

Experimental top

A mixture of 2.01 g (0.01 mol) 5-amino-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde and 1.32 g (0.01 mol) of 2,5-dimethoxytetrahydrofuran in acetic acid (15 ml) was heated under reflux for 2 h. After cooling the mixture was poured into cold water (50 ml) and the precipitate was filtered off, washed with water, dried under vacuum and crystallized from dioxane-water (3:1vv) to afford the product in 85% yield. Colourless plate-like crystals for X-ray diffraction were obtained by further crystallization of the product from acetic acid. M.p. 409 – 411 K.

Computing details top

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXT (Bruker, 2014); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Perspective view of the title molecule with labeling scheme and 50% probability ellipsoids for non-H atoms.
	Fig. 2. Packing viewed down the c axis showing an edge view of one corrugated sheet with hydrogen bonds drawn as red and blue dashed lines.
	Fig. 3. Packing viewed down the a axis showing the C—H···O and C—H···N interactions as red and blue dashed lines, respectively.

3-Methyl-1-phenyl-5-(1H-pyrrol-1-yl)-1H-pyrazole-4-carbaldehyde top

Crystal data top

C₁₅H₁₃N₃O	F(000) = 528
M_r = 251.28	D_x = 1.317 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.5807 (8) Å	Cell parameters from 6992 reflections
b = 15.1720 (13) Å	θ = 2.5–29.1°
c = 8.7370 (8) Å	µ = 0.09 mm⁻¹
β = 93.6180 (11)°	T = 150 K
V = 1267.46 (19) Å³	Plate, colourless
Z = 4	0.29 × 0.17 × 0.04 mm

Data collection top

Bruker SMART APEX CCD diffractometer	3321 independent reflections
Radiation source: fine-focus sealed tube	2527 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.053
Detector resolution: 8.3660 pixels mm^-1	θ_max = 29.2°, θ_min = 2.1°
ϕ and ω scans	h = −13→13
Absorption correction: multi-scan (SADABS; Bruker, 2014)	k = −20→20
T_min = 0.98, T_max = 1.00	l = −11→11
26282 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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.114	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0533P)² + 0.2193P] where P = (F_o² + 2F_c²)/3
3321 reflections	(Δ/σ)_max < 0.001
173 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₅H₁₃N₃O	V = 1267.46 (19) Å³
M_r = 251.28	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.5807 (8) Å	µ = 0.09 mm⁻¹
b = 15.1720 (13) Å	T = 150 K
c = 8.7370 (8) Å	0.29 × 0.17 × 0.04 mm
β = 93.6180 (11)°

Data collection top

Bruker SMART APEX CCD diffractometer	3321 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2014)	2527 reflections with I > 2σ(I)
T_min = 0.98, T_max = 1.00	R_int = 0.053
26282 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.114	H-atom parameters constrained
S = 1.07	Δρ_max = 0.31 e Å⁻³
3321 reflections	Δρ_min = −0.25 e Å⁻³
173 parameters

Special details top

Experimental. The diffraction data were collected in three sets of

400 frames (0.5° width in ω) at ϕ = 0, 120

and 240°. A scan time of 80 sec/frame was used.

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. H-atoms attached to carbon

were placed in calculated positions (C—H = 0.95 - 0.98 Å). All were

included as riding contributions with isotropic displacement parameters

1.2 - 1.5 times those of the attached atoms.

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

	x	y	z	U_iso*/U_eq
O1	0.33317 (10)	0.54403 (7)	0.91467 (11)	0.0336 (2)
N1	0.59037 (11)	0.76421 (7)	0.80193 (12)	0.0234 (2)
N2	0.67710 (11)	0.71108 (7)	0.72255 (12)	0.0211 (2)
N3	0.70035 (11)	0.55911 (6)	0.64732 (12)	0.0210 (2)
C1	0.63304 (13)	0.62637 (8)	0.72276 (14)	0.0208 (3)
C2	0.51547 (13)	0.62272 (8)	0.80704 (14)	0.0217 (3)
C3	0.49451 (13)	0.71148 (8)	0.85367 (14)	0.0230 (3)
C4	0.38179 (14)	0.74728 (10)	0.94605 (16)	0.0306 (3)
H4A	0.3977	0.8103	0.9644	0.046*
H4B	0.3827	0.7162	1.0445	0.046*
H4C	0.2909	0.7388	0.8901	0.046*
C5	0.43357 (14)	0.54534 (9)	0.83563 (15)	0.0253 (3)
H5	0.4597	0.4916	0.7896	0.030*
C6	0.79899 (13)	0.74965 (8)	0.66330 (14)	0.0206 (3)
C7	0.92330 (13)	0.70303 (8)	0.66282 (14)	0.0242 (3)
H7	0.9285	0.6441	0.6997	0.029*
C8	1.03977 (14)	0.74327 (9)	0.60798 (15)	0.0269 (3)
H8	1.1251	0.7115	0.6063	0.032*
C9	1.03304 (14)	0.82956 (9)	0.55550 (15)	0.0276 (3)
H9	1.1131	0.8567	0.5172	0.033*
C10	0.90846 (15)	0.87586 (9)	0.55948 (15)	0.0276 (3)
H10	0.9040	0.9354	0.5256	0.033*
C11	0.79111 (13)	0.83644 (8)	0.61199 (15)	0.0240 (3)
H11	0.7057	0.8682	0.6132	0.029*
C12	0.76608 (14)	0.48753 (8)	0.71948 (15)	0.0250 (3)
H12	0.7625	0.4720	0.8245	0.030*
C13	0.83647 (15)	0.44366 (9)	0.61277 (15)	0.0288 (3)
H13	0.8913	0.3920	0.6299	0.035*
C14	0.81336 (14)	0.48874 (9)	0.47146 (15)	0.0276 (3)
H14	0.8493	0.4722	0.3767	0.033*
C15	0.73103 (14)	0.55959 (8)	0.49470 (14)	0.0240 (3)
H15	0.7001	0.6018	0.4198	0.029*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0322 (5)	0.0361 (6)	0.0335 (5)	−0.0085 (4)	0.0099 (4)	0.0015 (4)
N1	0.0209 (5)	0.0216 (5)	0.0282 (6)	0.0022 (4)	0.0048 (4)	−0.0046 (4)
N2	0.0209 (5)	0.0177 (5)	0.0251 (5)	0.0001 (4)	0.0044 (4)	−0.0023 (4)
N3	0.0249 (5)	0.0171 (5)	0.0214 (5)	0.0011 (4)	0.0038 (4)	−0.0007 (4)
C1	0.0233 (6)	0.0172 (6)	0.0216 (6)	−0.0004 (5)	0.0002 (5)	−0.0002 (4)
C2	0.0217 (6)	0.0222 (6)	0.0211 (6)	−0.0005 (5)	0.0012 (5)	−0.0007 (5)
C3	0.0214 (6)	0.0242 (6)	0.0232 (6)	0.0006 (5)	0.0007 (5)	−0.0024 (5)
C4	0.0258 (7)	0.0327 (7)	0.0341 (7)	0.0010 (6)	0.0071 (6)	−0.0065 (6)
C5	0.0274 (6)	0.0254 (6)	0.0229 (6)	−0.0033 (5)	0.0008 (5)	0.0006 (5)
C6	0.0218 (6)	0.0197 (6)	0.0204 (6)	−0.0025 (5)	0.0033 (5)	−0.0022 (5)
C7	0.0249 (6)	0.0208 (6)	0.0270 (6)	0.0007 (5)	0.0028 (5)	−0.0009 (5)
C8	0.0234 (6)	0.0277 (7)	0.0299 (7)	−0.0003 (5)	0.0044 (5)	−0.0049 (5)
C9	0.0279 (7)	0.0279 (7)	0.0275 (7)	−0.0077 (5)	0.0067 (5)	−0.0042 (5)
C10	0.0331 (7)	0.0214 (6)	0.0284 (7)	−0.0041 (5)	0.0026 (5)	0.0005 (5)
C11	0.0253 (6)	0.0192 (6)	0.0272 (6)	0.0010 (5)	0.0005 (5)	−0.0011 (5)
C12	0.0315 (7)	0.0184 (6)	0.0250 (6)	0.0016 (5)	0.0002 (5)	0.0021 (5)
C13	0.0342 (7)	0.0209 (6)	0.0313 (7)	0.0062 (5)	0.0012 (6)	−0.0015 (5)
C14	0.0318 (7)	0.0276 (7)	0.0238 (6)	0.0024 (5)	0.0043 (5)	−0.0041 (5)
C15	0.0294 (7)	0.0234 (6)	0.0195 (6)	0.0012 (5)	0.0028 (5)	0.0002 (5)

Geometric parameters (Å, º) top

O1—C5	1.2191 (16)	C6—C11	1.3915 (17)
N1—C3	1.3191 (16)	C7—C8	1.3838 (18)
N1—N2	1.3762 (14)	C7—H7	0.9500
N2—C1	1.3529 (15)	C8—C9	1.3873 (19)
N2—C6	1.4319 (15)	C8—H8	0.9500
N3—C15	1.3835 (16)	C9—C10	1.3873 (19)
N3—C12	1.3869 (16)	C9—H9	0.9500
N3—C1	1.3946 (15)	C10—C11	1.3775 (18)
C1—C2	1.3852 (17)	C10—H10	0.9500
C2—C3	1.4248 (17)	C11—H11	0.9500
C2—C5	1.4427 (17)	C12—C13	1.3589 (19)
C3—C4	1.4909 (17)	C12—H12	0.9500
C4—H4A	0.9800	C13—C14	1.4165 (19)
C4—H4B	0.9800	C13—H13	0.9500
C4—H4C	0.9800	C14—C15	1.3562 (18)
C5—H5	0.9500	C14—H14	0.9500
C6—C7	1.3854 (17)	C15—H15	0.9500

C3—N1—N2	105.85 (10)	C8—C7—C6	119.21 (12)
C1—N2—N1	110.94 (10)	C8—C7—H7	120.4
C1—N2—C6	130.57 (10)	C6—C7—H7	120.4
N1—N2—C6	118.36 (10)	C7—C8—C9	120.60 (12)
C15—N3—C12	108.92 (10)	C7—C8—H8	119.7
C15—N3—C1	125.76 (10)	C9—C8—H8	119.7
C12—N3—C1	124.63 (10)	C10—C9—C8	119.45 (12)
N2—C1—C2	107.63 (10)	C10—C9—H9	120.3
N2—C1—N3	122.74 (11)	C8—C9—H9	120.3
C2—C1—N3	129.63 (11)	C11—C10—C9	120.67 (12)
C1—C2—C3	104.38 (11)	C11—C10—H10	119.7
C1—C2—C5	126.44 (11)	C9—C10—H10	119.7
C3—C2—C5	129.17 (12)	C10—C11—C6	119.30 (12)
N1—C3—C2	111.19 (11)	C10—C11—H11	120.4
N1—C3—C4	120.56 (11)	C6—C11—H11	120.4
C2—C3—C4	128.25 (12)	C13—C12—N3	107.60 (11)
C3—C4—H4A	109.5	C13—C12—H12	126.2
C3—C4—H4B	109.5	N3—C12—H12	126.2
H4A—C4—H4B	109.5	C12—C13—C14	107.73 (12)
C3—C4—H4C	109.5	C12—C13—H13	126.1
H4A—C4—H4C	109.5	C14—C13—H13	126.1
H4B—C4—H4C	109.5	C15—C14—C13	108.21 (12)
O1—C5—C2	124.65 (12)	C15—C14—H14	125.9
O1—C5—H5	117.7	C13—C14—H14	125.9
C2—C5—H5	117.7	C14—C15—N3	107.53 (11)
C7—C6—C11	120.75 (11)	C14—C15—H15	126.2
C7—C6—N2	120.88 (11)	N3—C15—H15	126.2
C11—C6—N2	118.31 (11)

C3—N1—N2—C1	1.28 (13)	C3—C2—C5—O1	−4.1 (2)
C3—N1—N2—C6	−174.98 (10)	C1—N2—C6—C7	−32.38 (19)
N1—N2—C1—C2	−1.18 (13)	N1—N2—C6—C7	143.01 (12)
C6—N2—C1—C2	174.49 (11)	C1—N2—C6—C11	150.22 (13)
N1—N2—C1—N3	178.45 (10)	N1—N2—C6—C11	−34.39 (16)
C6—N2—C1—N3	−5.88 (19)	C11—C6—C7—C8	−1.13 (19)
C15—N3—C1—N2	−53.33 (18)	N2—C6—C7—C8	−178.47 (11)
C12—N3—C1—N2	116.10 (14)	C6—C7—C8—C9	0.68 (19)
C15—N3—C1—C2	126.21 (14)	C7—C8—C9—C10	0.54 (19)
C12—N3—C1—C2	−64.36 (19)	C8—C9—C10—C11	−1.3 (2)
N2—C1—C2—C3	0.59 (13)	C9—C10—C11—C6	0.87 (19)
N3—C1—C2—C3	−179.00 (12)	C7—C6—C11—C10	0.37 (19)
N2—C1—C2—C5	179.33 (11)	N2—C6—C11—C10	177.77 (11)
N3—C1—C2—C5	−0.3 (2)	C15—N3—C12—C13	−0.26 (15)
N2—N1—C3—C2	−0.88 (14)	C1—N3—C12—C13	−171.20 (11)
N2—N1—C3—C4	−179.99 (11)	N3—C12—C13—C14	−0.27 (15)
C1—C2—C3—N1	0.20 (14)	C12—C13—C14—C15	0.71 (16)
C5—C2—C3—N1	−178.50 (12)	C13—C14—C15—N3	−0.86 (15)
C1—C2—C3—C4	179.21 (12)	C12—N3—C15—C14	0.70 (15)
C5—C2—C3—C4	0.5 (2)	C1—N3—C15—C14	171.52 (12)
C1—C2—C5—O1	177.49 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···N1ⁱ	0.95	2.48	3.3931 (17)	161
C12—H12···O1ⁱⁱ	0.95	2.52	3.4255 (17)	159

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···N1ⁱ	0.95	2.48	3.3931 (17)	161
C12—H12···O1ⁱⁱ	0.95	2.52	3.4255 (17)	159

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

Acknowledgements

The authors would like to thank Professor Hussein M. S. El-Kashef for his contribution to this study. JTM would like to express his thanks to Tulane University for support of the Tulane Crystallography Laboratory.

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ISSN: 2056-9890

Volume 70| Part 10| October 2014| Pages o1131-o1132

doi:10.1107/S1600536814020984

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

Crystal structure of 3-methyl-1-phenyl-5-(1H-pyrrol-1-yl)-1H-pyrazole-4-carbaldehyde

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds