Crystal structure of (E)-N-{[3-methyl-1-phenyl-5-(1H-pyrrol-1-yl)-1H-pyrazol-4-yl]methyl­idene}hydroxyl­amine

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

doi:10.1107/S1600536814023514

organic compounds

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ISSN: 2056-9890

Volume 70| Part 11| November 2014| Pages o1216-o1217

doi:10.1107/S1600536814023514

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Crystal structure of (E)-N-{[3-methyl-1-phenyl-5-(1H-pyrrol-1-yl)-1H-pyrazol-4-yl]methylidene}hydroxylamine

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 W. T. A. Harrison, University of Aberdeen, Scotland (Received 25 October 2014; accepted 25 October 2014; online 31 October 2014)

The title compound, C₁₅H₁₄N₄O, crystallizes with two molecules in the asymmetric unit with similar conformations (r.m.s. overlay fit for the 20 non-H atoms = 0.175 Å). In the first molecule, the dihedral angles between the planes of the central pyrazole ring and the pendant phenyl and pyrrole rings are 42.69 (8) and 51.88 (6)°, respectively, with corresponding angles of 54.49 (7) and 49.61 (9)°, respectively, in the second molecule. In the crystal, the two molecules, together with their inversion-symmetry counterparts, are linked into tetramers by O—H⋯N hydrogen bonds. The tetramers form layers parallel to (211) through pairwise C—H⋯π interactions.

Keywords: crystal structure; pyrrole ring; hydrogen bonding; hydroxylamine.

CCDC reference: 1031015

1. Related literature

For use of pyrazoles in synthesis of polyfunctionally substituted heterocycles, see: Elnagdi et al. (1987 ); Quiroga et al. (2007 , 2008a ,b ); Aly et al. (1994 ). For pharmaceutical properties of pyrazole-containing compounds, see: Bazgir et al. (2008 ); Dias et al. (1994 ); El-Kashef et al. (2000 ); El-Emary et al. (2002 ).

2. Experimental

2.1. Crystal data

C₁₅H₁₄N₄O
M_r = 266.30
Triclinic, $[P \overline 1]$
a = 9.1497 (2) Å
b = 12.3932 (3) Å
c = 12.7294 (3) Å
α = 87.4070 (11)°
β = 82.6740 (12)°
γ = 75.0190 (12)°
V = 1382.88 (6) Å³
Z = 4
Cu Kα radiation
μ = 0.68 mm⁻¹
T = 150 K
0.22 × 0.15 × 0.05 mm

2.2. Data collection

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2014 ) T_min = 0.92, T_max = 0.97
15570 measured reflections
5370 independent reflections
4088 reflections with I > 2σ(I)
R_int = 0.036

2.3. Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.108
S = 1.04
5370 reflections
363 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is centroid of C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯N2ⁱ	0.84	1.95	2.7835 (19)	174
O1—H1A⋯N6ⁱⁱ	0.84	1.99	2.8277 (19)	172
C11—H11⋯Cgⁱⁱ	0.95	3.45	?	170
Symmetry codes: (i) x, y+1, z; (ii) -x+1, -y, -z+2.

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT; program(s) used to solve structure: SHELXT (Sheldrick, 2008 ); 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: 1031015

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536814023514/hb7307sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814023514/hb7307Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814023514/hb7307Isup3.cml

checkCIF report

Comment top

Pyrazoles are interested class of heterocyclic compounds for chemists and pharmacists due to their diverse synthetic and biological applications. Pyrazoles are excellent precursors for the synthesis of condensed polyfunctionally substituted heterocycles (Elnagdi et al., 1987; Quiroga et al., 2007; Quiroga et al., 2008a,b; Aly et al., 1994). Moreover, pyrazole containing compounds exhibit a broad spectrum of pharmaceutical properties such as anti-hyperglycemic and analgesic (Bazgir, et al., 2008), anti-parasitic (Dias et al., 1994) anti-microbial (El-Kashef et al., 2000) and anti-schistosomal activities (El-Emary et al., 2002). Following our on-going study in the synthesis and characterization of new bio-active heterocyclic compounds, we report here the crystal structure determination of the title compound.

There are two independent molecules of the title compound in the asymmetric unit which differ primarily in the orientation of the pendant phenyl and pyrrolyl rings. Thus the dihedral angles between these rings, respectively, and the central heterocyclic ring are 42.69 (8) and 51.88 (6)° in molecule 1 but 54.49 (7) and 49.61 (9)° in molecule 2. Molecules 1 at x, y, z and 1 - x, -1 - y, 2 - z and molecules 2 at x, -1 + y, z and 1 - x, -y, 2 - z are associated into a cyclic tetramer via O—H···N(2 or 6) hydrogen bonds (Table 1 and Fig. 2). These units form sheets approximately parallel to (100) (Fig. 2) in which the major inter-tetramer interaction within the sheet appears to be pairwise C—H···π (C11—H11···Cg: H···Cg = 3.45 Å, C—H···Cg = 170° (Cg is centroid of C1–C6 ring at 1 - x, -y, 2 - z).

Related literature top

For use of pyrazoles in synthesis of polyfunctionally substituted heterocycles, see: Elnagdi et al. (1987); Quiroga et al. (2007, 2008a,b); Aly et al. (1994). For pharmaceutical properties of pyrazole-containing compounds, see: Bazgir et al. (2008); Dias et al. (1994); El-Kashef et al. (2000); El-Emary et al. (2002).

Experimental top

A mixture of 760 mg (3 mmol) 3-methyl-1-phenyl-5-(1H-pyrrol-1-yl)-4,5-dihydro-1H-pyrazole-4-carbaldehyde and 208.5 mg (3 mmol) of hydroxylamine hydrochloride in 15 ml pyridine was heated under reflux for 3 h. After cooling, the reaction mixture was poured into cold water. The resulting solid product was filtered, washed with water, dried under vacuum and crystallized from dioxane to give colourless plates Yield 76%, m.p. 463–465 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 (Sheldrick, 2008); 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

The asymmetric unit of the title compound with 50% probability ellipsoids.

Packing of three H-bonded tetramers viewed down the a axis. O—H···N hydrogen bonds are shown by dotted lines.

Elevation view of the layers of H-bonded tetramers.

(E)-N-{[3-Methyl-1-phenyl-5-(1H-pyrrol-1-yl)-1H-pyrazol-4-yl]methylidene}hydroxylamine top

Crystal data top

C₁₅H₁₄N₄O	Z = 4
M_r = 266.30	F(000) = 560
Triclinic, P1	D_x = 1.279 Mg m⁻³
a = 9.1497 (2) Å	Cu Kα radiation, λ = 1.54178 Å
b = 12.3932 (3) Å	Cell parameters from 8765 reflections
c = 12.7294 (3) Å	θ = 3.5–72.2°
α = 87.4070 (11)°	µ = 0.68 mm⁻¹
β = 82.6740 (12)°	T = 150 K
γ = 75.0190 (12)°	Plate, colourless
V = 1382.88 (6) Å³	0.22 × 0.15 × 0.05 mm

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	5370 independent reflections
Radiation source: INCOATEC IµS micro-focus source	4088 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.036
Detector resolution: 10.4167 pixels mm^-1	θ_max = 72.4°, θ_min = 3.5°
ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2014)	k = −15→15
T_min = 0.92, T_max = 0.97	l = −15→15
15570 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)] = 0.042	Hydrogen site location: mixed
wR(F²) = 0.108	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0468P)² + 0.401P] where P = (F_o² + 2F_c²)/3
5370 reflections	(Δ/σ)_max = 0.001
363 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₅H₁₄N₄O	γ = 75.0190 (12)°
M_r = 266.30	V = 1382.88 (6) Å³
Triclinic, P1	Z = 4
a = 9.1497 (2) Å	Cu Kα radiation
b = 12.3932 (3) Å	µ = 0.68 mm⁻¹
c = 12.7294 (3) Å	T = 150 K
α = 87.4070 (11)°	0.22 × 0.15 × 0.05 mm
β = 82.6740 (12)°

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	5370 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2014)	4088 reflections with I > 2σ(I)
T_min = 0.92, T_max = 0.97	R_int = 0.036
15570 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.108	H-atom parameters constrained
S = 1.04	Δρ_max = 0.32 e Å⁻³
5370 reflections	Δρ_min = −0.18 e Å⁻³
363 parameters

Special details top

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) while those

attached to oxygen were placed in locations derived from a difference

map and their parameters adjusted to give O—H = 0.84 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	0.01620 (14)	−0.14968 (11)	1.23494 (9)	0.0350 (3)
H1A	0.0512	−0.2083	1.2691	0.042*
N1	0.32895 (16)	0.00206 (11)	0.85512 (11)	0.0253 (3)
N2	0.33432 (17)	−0.10531 (12)	0.83004 (11)	0.0283 (3)
N3	0.23015 (16)	0.13164 (11)	0.99916 (11)	0.0265 (3)
N4	0.11882 (17)	−0.16601 (13)	1.14130 (11)	0.0305 (3)
N5	0.86241 (16)	0.34350 (11)	0.53889 (10)	0.0260 (3)
C1	0.40366 (18)	0.06699 (13)	0.78205 (13)	0.0252 (3)
C2	0.39036 (19)	0.06265 (14)	0.67514 (13)	0.0281 (4)
H2	0.3287	0.0198	0.6516	0.034*
C3	0.4681 (2)	0.12150 (15)	0.60299 (14)	0.0318 (4)
H3	0.4610	0.1181	0.5295	0.038*
C4	0.5558 (2)	0.18502 (15)	0.63761 (15)	0.0332 (4)
H4	0.6089	0.2251	0.5878	0.040*
C5	0.5667 (2)	0.19049 (15)	0.74439 (15)	0.0323 (4)
H5	0.6256	0.2356	0.7678	0.039*
C6	0.49199 (19)	0.13047 (14)	0.81776 (14)	0.0294 (4)
H6	0.5011	0.1328	0.8911	0.035*
C7	0.25257 (19)	0.02755 (14)	0.95310 (13)	0.0248 (3)
C8	0.20937 (19)	−0.06590 (14)	0.99446 (13)	0.0256 (3)
C9	0.2641 (2)	−0.14714 (14)	0.91388 (13)	0.0282 (4)
C10	0.2486 (3)	−0.26404 (15)	0.91273 (16)	0.0423 (5)
H10A	0.2917	−0.2969	0.8434	0.063*
H10B	0.1406	−0.2636	0.9260	0.063*
H10C	0.3034	−0.3084	0.9680	0.063*
C11	0.2741 (3)	0.14651 (16)	1.09638 (15)	0.0413 (5)
H11	0.3152	0.0889	1.1443	0.050*
C12	0.2485 (3)	0.25693 (18)	1.11112 (17)	0.0558 (6)
H12	0.2681	0.2911	1.1713	0.067*
C13	0.1869 (3)	0.31322 (15)	1.02105 (16)	0.0416 (5)
H13	0.1580	0.3918	1.0101	0.050*
C14	0.1765 (2)	0.23523 (14)	0.95337 (14)	0.0295 (4)
H14	0.1392	0.2492	0.8865	0.035*
C15	0.1185 (2)	−0.07129 (14)	1.09604 (13)	0.0273 (4)
H15	0.0587	−0.0044	1.1291	0.033*
O2	0.49919 (16)	0.78935 (10)	0.64738 (10)	0.0386 (3)
H2A	0.4532	0.8172	0.7052	0.046*
N6	0.84165 (17)	0.33808 (12)	0.64741 (11)	0.0284 (3)
N7	0.79776 (16)	0.47398 (11)	0.39594 (11)	0.0261 (3)
N8	0.56651 (17)	0.67789 (12)	0.67161 (12)	0.0315 (3)
C16	0.94172 (19)	0.24537 (13)	0.47988 (13)	0.0257 (4)
C17	1.0867 (2)	0.18970 (15)	0.50007 (14)	0.0334 (4)
H17	1.1349	0.2169	0.5513	0.040*
C18	1.1611 (2)	0.09363 (17)	0.44459 (15)	0.0391 (5)
H18	1.2611	0.0546	0.4578	0.047*
C19	1.0912 (2)	0.05402 (16)	0.37017 (15)	0.0362 (4)
H19	1.1428	−0.0123	0.3327	0.043*
C20	0.9459 (2)	0.11116 (16)	0.35027 (14)	0.0340 (4)
H20	0.8981	0.0843	0.2987	0.041*
C21	0.8700 (2)	0.20730 (15)	0.40525 (13)	0.0302 (4)
H21	0.7702	0.2466	0.3919	0.036*
C22	0.78947 (19)	0.44542 (14)	0.50370 (13)	0.0255 (3)
C23	0.7165 (2)	0.50922 (14)	0.59080 (13)	0.0266 (4)
C24	0.7529 (2)	0.43701 (14)	0.67857 (13)	0.0284 (4)
C25	0.7069 (2)	0.45931 (16)	0.79421 (14)	0.0374 (4)
H25A	0.7502	0.3924	0.8352	0.056*
H25B	0.5955	0.4784	0.8089	0.056*
H25C	0.7447	0.5216	0.8142	0.056*
C26	0.6762 (2)	0.52578 (16)	0.34263 (14)	0.0352 (4)
H26	0.5721	0.5447	0.3718	0.042*
C27	0.7302 (2)	0.54509 (17)	0.24161 (15)	0.0400 (5)
H27	0.6712	0.5800	0.1874	0.048*
C28	0.8895 (2)	0.5042 (2)	0.23135 (16)	0.0507 (6)
H28	0.9576	0.5067	0.1689	0.061*
C29	0.9289 (2)	0.46064 (19)	0.32625 (16)	0.0435 (5)
H29	1.0294	0.4268	0.3420	0.052*
C30	0.6353 (2)	0.62612 (14)	0.58742 (14)	0.0304 (4)
H30	0.6330	0.6651	0.5214	0.036*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0406 (7)	0.0345 (7)	0.0262 (6)	−0.0060 (6)	0.0012 (5)	0.0040 (5)
N1	0.0317 (8)	0.0214 (7)	0.0232 (7)	−0.0070 (6)	−0.0033 (6)	−0.0022 (5)
N2	0.0361 (8)	0.0216 (7)	0.0272 (7)	−0.0071 (6)	−0.0033 (6)	−0.0031 (6)
N3	0.0352 (8)	0.0225 (7)	0.0221 (7)	−0.0070 (6)	−0.0049 (6)	−0.0021 (5)
N4	0.0335 (8)	0.0375 (9)	0.0211 (7)	−0.0105 (7)	−0.0022 (6)	−0.0008 (6)
N5	0.0319 (8)	0.0248 (7)	0.0210 (7)	−0.0067 (6)	−0.0034 (6)	0.0009 (5)
C1	0.0248 (8)	0.0224 (8)	0.0262 (8)	−0.0032 (7)	−0.0008 (7)	0.0002 (6)
C2	0.0308 (9)	0.0255 (9)	0.0271 (9)	−0.0056 (7)	−0.0036 (7)	−0.0011 (7)
C3	0.0325 (10)	0.0320 (10)	0.0266 (9)	−0.0020 (8)	−0.0007 (7)	0.0019 (7)
C4	0.0292 (9)	0.0271 (9)	0.0389 (10)	−0.0035 (7)	0.0020 (8)	0.0066 (8)
C5	0.0253 (9)	0.0273 (9)	0.0446 (11)	−0.0074 (7)	−0.0051 (8)	0.0026 (8)
C6	0.0285 (9)	0.0275 (9)	0.0316 (9)	−0.0044 (7)	−0.0063 (7)	−0.0008 (7)
C7	0.0286 (9)	0.0231 (8)	0.0221 (8)	−0.0038 (7)	−0.0059 (6)	−0.0010 (6)
C8	0.0298 (9)	0.0232 (8)	0.0239 (8)	−0.0057 (7)	−0.0063 (7)	0.0008 (6)
C9	0.0351 (9)	0.0237 (9)	0.0260 (9)	−0.0076 (7)	−0.0045 (7)	0.0001 (7)
C10	0.0643 (14)	0.0278 (10)	0.0358 (11)	−0.0178 (9)	0.0049 (9)	−0.0050 (8)
C11	0.0660 (14)	0.0312 (10)	0.0289 (10)	−0.0105 (9)	−0.0182 (9)	−0.0006 (8)
C12	0.100 (2)	0.0328 (11)	0.0399 (12)	−0.0157 (12)	−0.0292 (12)	−0.0059 (9)
C13	0.0635 (14)	0.0210 (9)	0.0393 (11)	−0.0074 (9)	−0.0091 (9)	−0.0023 (8)
C14	0.0363 (10)	0.0240 (9)	0.0266 (9)	−0.0051 (7)	−0.0037 (7)	0.0013 (7)
C15	0.0331 (9)	0.0254 (9)	0.0236 (8)	−0.0060 (7)	−0.0069 (7)	0.0003 (7)
O2	0.0537 (8)	0.0263 (7)	0.0283 (7)	−0.0002 (6)	0.0026 (6)	−0.0024 (5)
N6	0.0396 (8)	0.0255 (7)	0.0213 (7)	−0.0102 (6)	−0.0049 (6)	0.0012 (6)
N7	0.0287 (8)	0.0253 (7)	0.0227 (7)	−0.0046 (6)	−0.0028 (6)	0.0021 (5)
N8	0.0392 (9)	0.0228 (7)	0.0317 (8)	−0.0064 (6)	−0.0045 (6)	−0.0008 (6)
C16	0.0295 (9)	0.0224 (8)	0.0238 (8)	−0.0054 (7)	−0.0012 (7)	0.0010 (6)
C17	0.0337 (10)	0.0336 (10)	0.0328 (10)	−0.0055 (8)	−0.0095 (8)	−0.0031 (8)
C18	0.0331 (10)	0.0384 (11)	0.0403 (11)	0.0039 (8)	−0.0095 (8)	−0.0042 (8)
C19	0.0395 (11)	0.0302 (10)	0.0338 (10)	−0.0001 (8)	−0.0011 (8)	−0.0070 (8)
C20	0.0373 (10)	0.0365 (10)	0.0281 (9)	−0.0086 (8)	−0.0033 (8)	−0.0079 (8)
C21	0.0270 (9)	0.0333 (10)	0.0294 (9)	−0.0048 (8)	−0.0049 (7)	−0.0028 (7)
C22	0.0273 (9)	0.0241 (8)	0.0249 (8)	−0.0067 (7)	−0.0033 (7)	0.0021 (6)
C23	0.0318 (9)	0.0236 (8)	0.0254 (8)	−0.0091 (7)	−0.0027 (7)	−0.0010 (7)
C24	0.0377 (10)	0.0235 (8)	0.0255 (9)	−0.0108 (7)	−0.0037 (7)	−0.0010 (7)
C25	0.0563 (13)	0.0294 (10)	0.0258 (9)	−0.0107 (9)	−0.0026 (8)	−0.0015 (7)
C26	0.0284 (9)	0.0405 (11)	0.0315 (10)	−0.0001 (8)	−0.0042 (7)	0.0047 (8)
C27	0.0421 (11)	0.0460 (12)	0.0281 (10)	−0.0041 (9)	−0.0072 (8)	0.0061 (8)
C28	0.0393 (12)	0.0726 (16)	0.0317 (11)	−0.0056 (11)	0.0043 (9)	0.0150 (10)
C29	0.0269 (10)	0.0621 (14)	0.0364 (11)	−0.0069 (9)	−0.0001 (8)	0.0143 (9)
C30	0.0385 (10)	0.0261 (9)	0.0256 (9)	−0.0068 (8)	−0.0029 (7)	−0.0004 (7)

Geometric parameters (Å, º) top

O1—N4	1.4078 (18)	C13—H13	0.9500
O1—H1A	0.8403	C14—H14	0.9500
N1—C7	1.358 (2)	C15—H15	0.9500
N1—N2	1.3695 (18)	O2—N8	1.3973 (18)
N1—C1	1.426 (2)	O2—H2A	0.8402
N2—C9	1.330 (2)	N6—C24	1.329 (2)
N3—C14	1.381 (2)	N7—C29	1.376 (2)
N3—C11	1.383 (2)	N7—C26	1.376 (2)
N3—C7	1.397 (2)	N7—C22	1.399 (2)
N4—C15	1.284 (2)	N8—C30	1.280 (2)
N5—C22	1.353 (2)	C16—C17	1.378 (2)
N5—N6	1.3713 (18)	C16—C21	1.384 (2)
N5—C16	1.434 (2)	C17—C18	1.383 (3)
C1—C2	1.386 (2)	C17—H17	0.9500
C1—C6	1.391 (2)	C18—C19	1.380 (3)
C2—C3	1.387 (2)	C18—H18	0.9500
C2—H2	0.9500	C19—C20	1.385 (3)
C3—C4	1.380 (3)	C19—H19	0.9500
C3—H3	0.9500	C20—C21	1.384 (2)
C4—C5	1.382 (3)	C20—H20	0.9500
C4—H4	0.9500	C21—H21	0.9500
C5—C6	1.389 (2)	C22—C23	1.385 (2)
C5—H5	0.9500	C23—C24	1.418 (2)
C6—H6	0.9500	C23—C30	1.449 (2)
C7—C8	1.379 (2)	C24—C25	1.496 (2)
C8—C9	1.421 (2)	C25—H25A	0.9800
C8—C15	1.454 (2)	C25—H25B	0.9800
C9—C10	1.493 (2)	C25—H25C	0.9800
C10—H10A	0.9800	C26—C27	1.351 (3)
C10—H10B	0.9800	C26—H26	0.9500
C10—H10C	0.9800	C27—C28	1.405 (3)
C11—C12	1.345 (3)	C27—H27	0.9500
C11—H11	0.9500	C28—C29	1.353 (3)
C12—C13	1.417 (3)	C28—H28	0.9500
C12—H12	0.9500	C29—H29	0.9500
C13—C14	1.352 (2)	C30—H30	0.9500

N4—O1—H1A	101.0	N4—C15—C8	120.32 (16)
C7—N1—N2	110.52 (13)	N4—C15—H15	119.8
C7—N1—C1	130.19 (14)	C8—C15—H15	119.8
N2—N1—C1	119.25 (13)	N8—O2—H2A	105.0
C9—N2—N1	106.20 (13)	C24—N6—N5	105.80 (13)
C14—N3—C11	108.69 (14)	C29—N7—C26	108.17 (15)
C14—N3—C7	127.03 (14)	C29—N7—C22	126.09 (15)
C11—N3—C7	123.98 (15)	C26—N7—C22	125.65 (15)
C15—N4—O1	109.56 (14)	C30—N8—O2	110.12 (14)
C22—N5—N6	110.63 (13)	C17—C16—C21	121.33 (16)
C22—N5—C16	129.45 (14)	C17—C16—N5	119.32 (15)
N6—N5—C16	119.70 (13)	C21—C16—N5	119.33 (15)
C2—C1—C6	120.97 (15)	C16—C17—C18	118.98 (17)
C2—C1—N1	118.81 (15)	C16—C17—H17	120.5
C6—C1—N1	120.18 (15)	C18—C17—H17	120.5
C1—C2—C3	119.25 (16)	C19—C18—C17	120.55 (18)
C1—C2—H2	120.4	C19—C18—H18	119.7
C3—C2—H2	120.4	C17—C18—H18	119.7
C4—C3—C2	120.24 (17)	C18—C19—C20	119.84 (17)
C4—C3—H3	119.9	C18—C19—H19	120.1
C2—C3—H3	119.9	C20—C19—H19	120.1
C3—C4—C5	120.27 (16)	C21—C20—C19	120.25 (17)
C3—C4—H4	119.9	C21—C20—H20	119.9
C5—C4—H4	119.9	C19—C20—H20	119.9
C4—C5—C6	120.36 (17)	C16—C21—C20	119.05 (16)
C4—C5—H5	119.8	C16—C21—H21	120.5
C6—C5—H5	119.8	C20—C21—H21	120.5
C5—C6—C1	118.88 (16)	N5—C22—C23	108.17 (14)
C5—C6—H6	120.6	N5—C22—N7	121.95 (15)
C1—C6—H6	120.6	C23—C22—N7	129.85 (15)
N1—C7—C8	107.93 (14)	C22—C23—C24	104.11 (15)
N1—C7—N3	122.85 (15)	C22—C23—C30	125.38 (15)
C8—C7—N3	129.20 (15)	C24—C23—C30	130.28 (16)
C7—C8—C9	104.66 (15)	N6—C24—C23	111.28 (15)
C7—C8—C15	125.06 (15)	N6—C24—C25	119.72 (15)
C9—C8—C15	130.16 (15)	C23—C24—C25	129.00 (16)
N2—C9—C8	110.67 (15)	C24—C25—H25A	109.5
N2—C9—C10	120.20 (15)	C24—C25—H25B	109.5
C8—C9—C10	129.11 (16)	H25A—C25—H25B	109.5
C9—C10—H10A	109.5	C24—C25—H25C	109.5
C9—C10—H10B	109.5	H25A—C25—H25C	109.5
H10A—C10—H10B	109.5	H25B—C25—H25C	109.5
C9—C10—H10C	109.5	C27—C26—N7	108.32 (16)
H10A—C10—H10C	109.5	C27—C26—H26	125.8
H10B—C10—H10C	109.5	N7—C26—H26	125.8
C12—C11—N3	107.90 (17)	C26—C27—C28	107.58 (17)
C12—C11—H11	126.1	C26—C27—H27	126.2
N3—C11—H11	126.1	C28—C27—H27	126.2
C11—C12—C13	107.91 (17)	C29—C28—C27	107.87 (18)
C11—C12—H12	126.0	C29—C28—H28	126.1
C13—C12—H12	126.0	C27—C28—H28	126.1
C14—C13—C12	107.91 (17)	C28—C29—N7	108.05 (17)
C14—C13—H13	126.0	C28—C29—H29	126.0
C12—C13—H13	126.0	N7—C29—H29	126.0
C13—C14—N3	107.60 (16)	N8—C30—C23	121.29 (16)
C13—C14—H14	126.2	N8—C30—H30	119.4
N3—C14—H14	126.2	C23—C30—H30	119.4

C7—N1—N2—C9	−1.45 (18)	C22—N5—N6—C24	1.11 (18)
C1—N1—N2—C9	176.40 (14)	C16—N5—N6—C24	−173.96 (14)
C7—N1—C1—C2	−139.98 (18)	C22—N5—C16—C17	130.07 (19)
N2—N1—C1—C2	42.7 (2)	N6—N5—C16—C17	−55.9 (2)
C7—N1—C1—C6	42.0 (3)	C22—N5—C16—C21	−51.1 (2)
N2—N1—C1—C6	−135.32 (16)	N6—N5—C16—C21	122.89 (17)
C6—C1—C2—C3	0.8 (3)	C21—C16—C17—C18	−0.3 (3)
N1—C1—C2—C3	−177.12 (15)	N5—C16—C17—C18	178.50 (16)
C1—C2—C3—C4	−1.0 (3)	C16—C17—C18—C19	0.0 (3)
C2—C3—C4—C5	0.0 (3)	C17—C18—C19—C20	0.4 (3)
C3—C4—C5—C6	1.2 (3)	C18—C19—C20—C21	−0.5 (3)
C4—C5—C6—C1	−1.4 (3)	C17—C16—C21—C20	0.2 (3)
C2—C1—C6—C5	0.4 (3)	N5—C16—C21—C20	−178.57 (16)
N1—C1—C6—C5	178.29 (15)	C19—C20—C21—C16	0.2 (3)
N2—N1—C7—C8	1.27 (19)	N6—N5—C22—C23	−0.78 (19)
C1—N1—C7—C8	−176.28 (16)	C16—N5—C22—C23	173.68 (16)
N2—N1—C7—N3	179.80 (14)	N6—N5—C22—N7	177.44 (14)
C1—N1—C7—N3	2.3 (3)	C16—N5—C22—N7	−8.1 (3)
C14—N3—C7—N1	49.0 (2)	C29—N7—C22—N5	−50.5 (3)
C11—N3—C7—N1	−124.05 (19)	C26—N7—C22—N5	133.17 (18)
C14—N3—C7—C8	−132.8 (2)	C29—N7—C22—C23	127.3 (2)
C11—N3—C7—C8	54.1 (3)	C26—N7—C22—C23	−49.0 (3)
N1—C7—C8—C9	−0.57 (18)	N5—C22—C23—C24	0.14 (19)
N3—C7—C8—C9	−178.98 (16)	N7—C22—C23—C24	−177.89 (17)
N1—C7—C8—C15	−176.83 (15)	N5—C22—C23—C30	175.12 (16)
N3—C7—C8—C15	4.8 (3)	N7—C22—C23—C30	−2.9 (3)
N1—N2—C9—C8	1.07 (19)	N5—N6—C24—C23	−1.01 (19)
N1—N2—C9—C10	179.60 (16)	N5—N6—C24—C25	179.69 (15)
C7—C8—C9—N2	−0.32 (19)	C22—C23—C24—N6	0.6 (2)
C15—C8—C9—N2	175.67 (16)	C30—C23—C24—N6	−174.07 (17)
C7—C8—C9—C10	−178.69 (19)	C22—C23—C24—C25	179.77 (18)
C15—C8—C9—C10	−2.7 (3)	C30—C23—C24—C25	5.1 (3)
C14—N3—C11—C12	0.1 (2)	C29—N7—C26—C27	−0.3 (2)
C7—N3—C11—C12	174.20 (19)	C22—N7—C26—C27	176.57 (17)
N3—C11—C12—C13	0.0 (3)	N7—C26—C27—C28	0.1 (2)
C11—C12—C13—C14	0.0 (3)	C26—C27—C28—C29	0.2 (3)
C12—C13—C14—N3	0.0 (2)	C27—C28—C29—N7	−0.4 (3)
C11—N3—C14—C13	−0.1 (2)	C26—N7—C29—C28	0.5 (2)
C7—N3—C14—C13	−173.97 (17)	C22—N7—C29—C28	−176.44 (18)
O1—N4—C15—C8	−176.70 (14)	O2—N8—C30—C23	179.19 (15)
C7—C8—C15—N4	−160.65 (17)	C22—C23—C30—N8	177.58 (17)
C9—C8—C15—N4	24.1 (3)	C24—C23—C30—N8	−8.8 (3)

Hydrogen-bond geometry (Å, º) top

Cg is centroid of C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···N2ⁱ	0.84	1.95	2.7835 (19)	174
O1—H1A···N6ⁱⁱ	0.84	1.99	2.8277 (19)	172
C11—H11···Cgⁱⁱ	0.95	3.45	?	170

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

Hydrogen-bond geometry (Å, º) top

Cg is centroid of C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···N2ⁱ	0.84	1.95	2.7835 (19)	174
O1—H1A···N6ⁱⁱ	0.84	1.99	2.8277 (19)	172
C11—H11···Cgⁱⁱ	0.95	3.45	?	170

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

Acknowledgements

The support of NSF–MRI grant No. 1228232 for the purchase of the diffractometer is gratefully acknowledged. In addition, SKM and TIE would like to thank Professor H. M. S. El-Kashef for his contribution to this study.

References

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Volume 70| Part 11| November 2014| Pages o1216-o1217

doi:10.1107/S1600536814023514

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

Crystal structure of (E)-N-{[3-methyl-1-phenyl-5-(1H-pyrrol-1-yl)-1H-pyrazol-4-yl]methyl­­idene}hydroxyl­amine

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 (E)-N-{[3-methyl-1-phenyl-5-(1H-pyrrol-1-yl)-1H-pyrazol-4-yl]methylidene}hydroxylamine