1-(4-Methoxy-phen-yl)-3-phenyl-1H-pyrazol-5-amine.

The synthesis of the title compound, C(16)H(15)N(3)O, is regiospecific and single-crystal X-ray diffraction provides the only means of unambiguous structural analysis, with the benzene ring bonded to the imine C atom. The phenyl ring and the essentially planar (r.m.s. deviation 0.0354 Å) methoxy-benzene group are rotated by 29.41 (5) and 37.01 (5)°, respectively, from the central pyrazole ring. An inter-molecular N-H⋯N hydrogen bond links symmetry-related mol-ecules into a C(5) chain, which runs parallel to the b axis.

Related literature

For background to this study, see: Gavrin et al. (2007 ▶); Joshi et al. (1979 ▶); Michaux & Charlier (2004 ▶); Ossipov et al. (2004 ▶); Raffa (2001 ▶).

Experimental

Crystal data

C16H15N3O

M = 265.31

Orthorhombic,

a = 14.9638 (6) Å

b = 6.3639 (2) Å

c = 28.2466 (12) Å

V = 2689.87 (18) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.35 × 0.35 × 0.05 mm

Data collection

Bruker Kappa APEXII diffractometer

Absorption correction: none

11632 measured reflections

3019 independent reflections

2256 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.111

S = 1.02

3019 reflections

190 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.15 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXTL and local programs.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809015463/lh2810sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809015463/lh2810Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Enhanced figure: interactive version of Fig. 1

C16H15N3O	F(000) = 1120
Mr = 265.31	Dx = 1.310 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2475 reflections
a = 14.9638 (6) Å	θ = 2.7–28.6°
b = 6.3639 (2) Å	µ = 0.09 mm−1
c = 28.2466 (12) Å	T = 296 K
V = 2689.87 (18) Å3	Plate, colourless
Z = 8	0.35 × 0.35 × 0.05 mm

Bruker Kappa APEXII diffractometer	2256 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.031
graphite	θmax = 28.3°, θmin = 2.0°
φ and ω scans	h = −19→16
11632 measured reflections	k = −7→6
3019 independent reflections	l = −36→37

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: difference Fourier map
wR(F2) = 0.111	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.048P)2 + 0.671P] where P = (Fo2 + 2Fc2)/3
3019 reflections	(Δ/σ)max = 0.001
190 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.15 e Å−3

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.

	x	y	z	Uiso*/Ueq
O	0.37170 (8)	0.3584 (2)	0.56552 (3)	0.0537 (3)
N1	0.38199 (8)	0.10523 (19)	0.75399 (4)	0.0327 (3)
N2	0.37654 (8)	0.2595 (2)	0.78830 (4)	0.0357 (3)
N3	0.39632 (11)	−0.2693 (2)	0.74725 (6)	0.0506 (4)
H3NA	0.3945 (12)	−0.386 (3)	0.7646 (6)	0.057 (6)*
H3NB	0.3982 (15)	−0.264 (4)	0.7192 (8)	0.083 (8)*
C1	0.38472 (9)	0.1542 (2)	0.82878 (5)	0.0334 (3)
C2	0.39560 (10)	−0.0607 (3)	0.82140 (5)	0.0401 (4)
H2	0.4031	−0.1639	0.8444	0.048*
C3	0.39302 (9)	−0.0890 (2)	0.77325 (5)	0.0359 (3)
C4	0.37681 (9)	0.1656 (2)	0.70563 (4)	0.0317 (3)
C5	0.42957 (9)	0.0699 (3)	0.67137 (5)	0.0391 (4)
H5	0.4681	−0.0386	0.6797	0.047*
C6	0.42468 (10)	0.1361 (3)	0.62484 (5)	0.0414 (4)
H6	0.4586	0.0688	0.6018	0.050*
C7	0.36981 (9)	0.3015 (3)	0.61242 (5)	0.0379 (4)
C8	0.31728 (9)	0.3982 (2)	0.64632 (5)	0.0374 (3)
H8	0.2803	0.5097	0.6381	0.045*
C9	0.32044 (9)	0.3268 (2)	0.69274 (4)	0.0347 (3)
H9	0.2840	0.3887	0.7155	0.042*
C10	0.32253 (15)	0.5386 (4)	0.55199 (6)	0.0687 (6)
H10A	0.2604	0.5175	0.5591	0.103*
H10B	0.3296	0.5620	0.5186	0.103*
H10C	0.3442	0.6587	0.5691	0.103*
C11	0.38252 (9)	0.2644 (3)	0.87483 (5)	0.0354 (3)
C12	0.33514 (10)	0.4489 (3)	0.88095 (5)	0.0421 (4)
H12	0.3041	0.5073	0.8556	0.050*
C13	0.33371 (12)	0.5473 (3)	0.92489 (6)	0.0534 (4)
H13	0.3018	0.6714	0.9289	0.064*
C14	0.37933 (12)	0.4620 (3)	0.96249 (6)	0.0567 (5)
H14	0.3784	0.5285	0.9918	0.068*
C15	0.42634 (12)	0.2785 (3)	0.95670 (5)	0.0550 (5)
H15	0.4571	0.2207	0.9822	0.066*
C16	0.42822 (11)	0.1790 (3)	0.91320 (5)	0.0448 (4)
H16	0.4601	0.0546	0.9096	0.054*

	U11	U22	U33	U12	U13	U23
O	0.0695 (8)	0.0595 (9)	0.0320 (5)	0.0105 (6)	0.0029 (5)	0.0047 (5)
N1	0.0413 (6)	0.0248 (8)	0.0320 (5)	−0.0005 (5)	−0.0026 (4)	−0.0017 (4)
N2	0.0451 (7)	0.0306 (8)	0.0315 (5)	−0.0003 (5)	−0.0004 (5)	−0.0021 (5)
N3	0.0764 (10)	0.0275 (9)	0.0478 (8)	−0.0004 (7)	−0.0067 (7)	−0.0014 (7)
C1	0.0349 (7)	0.0311 (9)	0.0342 (6)	−0.0036 (6)	0.0004 (5)	0.0033 (6)
C2	0.0495 (8)	0.0308 (10)	0.0399 (7)	−0.0004 (7)	−0.0037 (6)	0.0071 (6)
C3	0.0386 (7)	0.0260 (9)	0.0430 (7)	−0.0005 (6)	−0.0046 (5)	0.0011 (6)
C4	0.0347 (7)	0.0290 (9)	0.0315 (6)	−0.0037 (6)	−0.0026 (5)	0.0003 (5)
C5	0.0389 (7)	0.0379 (10)	0.0406 (7)	0.0068 (6)	−0.0009 (6)	−0.0013 (6)
C6	0.0425 (8)	0.0448 (11)	0.0370 (7)	0.0064 (7)	0.0045 (6)	−0.0061 (6)
C7	0.0418 (7)	0.0405 (10)	0.0315 (6)	−0.0032 (6)	−0.0007 (5)	−0.0002 (6)
C8	0.0427 (8)	0.0324 (9)	0.0370 (7)	0.0053 (6)	−0.0031 (5)	−0.0006 (6)
C9	0.0373 (7)	0.0327 (9)	0.0342 (6)	0.0017 (6)	0.0012 (5)	−0.0048 (6)
C10	0.0913 (15)	0.0668 (16)	0.0481 (10)	0.0174 (12)	−0.0012 (9)	0.0197 (9)
C11	0.0380 (7)	0.0355 (10)	0.0328 (6)	−0.0062 (6)	0.0033 (5)	0.0032 (6)
C12	0.0463 (8)	0.0394 (10)	0.0406 (7)	0.0001 (7)	0.0015 (6)	0.0012 (7)
C13	0.0587 (10)	0.0483 (12)	0.0532 (9)	0.0046 (8)	0.0083 (7)	−0.0089 (8)
C14	0.0659 (11)	0.0678 (15)	0.0363 (8)	−0.0051 (10)	0.0071 (7)	−0.0104 (8)
C15	0.0639 (11)	0.0683 (15)	0.0329 (7)	−0.0030 (9)	−0.0023 (7)	0.0052 (8)
C16	0.0525 (9)	0.0436 (11)	0.0382 (7)	0.0026 (8)	0.0003 (6)	0.0046 (7)

O—C7	1.3736 (16)	C7—C8	1.3834 (19)
O—C10	1.415 (2)	C8—H8	0.9300
N1—N2	1.3820 (16)	C8—C9	1.3885 (18)
N1—C3	1.3607 (19)	C9—H9	0.9300
N1—C4	1.4211 (16)	C10—H10A	0.9600
N2—C1	1.3307 (17)	C10—H10B	0.9600
N3—H3NA	0.89 (2)	C10—H10C	0.9600
N3—H3NB	0.79 (2)	C11—C12	1.382 (2)
N3—C3	1.363 (2)	C11—C16	1.392 (2)
C1—C2	1.393 (2)	C12—H12	0.9300
C1—C11	1.4782 (19)	C12—C13	1.391 (2)
C2—H2	0.9300	C13—H13	0.9300
C2—C3	1.373 (2)	C13—C14	1.374 (2)
C4—C5	1.3896 (19)	C14—H14	0.9300
C4—C9	1.377 (2)	C14—C15	1.373 (3)
C5—H5	0.9300	C15—H15	0.9300
C5—C6	1.3823 (19)	C15—C16	1.383 (2)
C6—H6	0.9300	C16—H16	0.9300
C6—C7	1.380 (2)
C7—O—C10	117.63 (13)	C7—C8—C9	119.26 (14)
N2—N1—C3	111.85 (11)	H8—C8—C9	120.4
N2—N1—C4	118.61 (12)	C4—C9—C8	120.95 (13)
C3—N1—C4	129.54 (12)	C4—C9—H9	119.5
N1—N2—C1	103.86 (12)	C8—C9—H9	119.5
H3NA—N3—H3NB	126 (2)	O—C10—H10A	109.5
H3NA—N3—C3	113.9 (12)	O—C10—H10B	109.5
H3NB—N3—C3	120.3 (18)	O—C10—H10C	109.5
N2—C1—C2	112.11 (12)	H10A—C10—H10B	109.5
N2—C1—C11	121.01 (14)	H10A—C10—H10C	109.5
C2—C1—C11	126.87 (13)	H10B—C10—H10C	109.5
C1—C2—H2	127.1	C1—C11—C12	121.62 (13)
C1—C2—C3	105.89 (13)	C1—C11—C16	119.26 (14)
H2—C2—C3	127.1	C12—C11—C16	119.10 (14)
N1—C3—N3	123.63 (13)	C11—C12—H12	119.9
N1—C3—C2	106.28 (13)	C11—C12—C13	120.14 (15)
N3—C3—C2	130.03 (15)	H12—C12—C13	119.9
N1—C4—C5	121.32 (13)	C12—C13—H13	119.9
N1—C4—C9	119.27 (12)	C12—C13—C14	120.28 (17)
C5—C4—C9	119.38 (12)	H13—C13—C14	119.9
C4—C5—H5	120.1	C13—C14—H14	120.1
C4—C5—C6	119.90 (14)	C13—C14—C15	119.89 (15)
H5—C5—C6	120.1	H14—C14—C15	120.1
C5—C6—H6	119.8	C14—C15—H15	119.8
C5—C6—C7	120.38 (13)	C14—C15—C16	120.38 (15)
H6—C6—C7	119.8	H15—C15—C16	119.8
O—C7—C6	115.73 (13)	C11—C16—C15	120.20 (16)
O—C7—C8	124.18 (14)	C11—C16—H16	119.9
C6—C7—C8	120.09 (13)	C15—C16—H16	119.9
C7—C8—H8	120.4
C3—N1—N2—C1	0.13 (14)	C10—O—C7—C8	5.6 (2)
C4—N1—N2—C1	−179.13 (11)	C5—C6—C7—O	178.30 (14)
N1—N2—C1—C2	0.31 (15)	C5—C6—C7—C8	−1.9 (2)
N1—N2—C1—C11	179.87 (11)	O—C7—C8—C9	179.71 (14)
N2—C1—C2—C3	−0.62 (17)	C6—C7—C8—C9	−0.1 (2)
C11—C1—C2—C3	179.85 (13)	N1—C4—C9—C8	176.33 (13)
N2—N1—C3—N3	176.99 (14)	C5—C4—C9—C8	−1.6 (2)
N2—N1—C3—C2	−0.51 (16)	C7—C8—C9—C4	1.8 (2)
C4—N1—C3—N3	−3.9 (2)	N2—C1—C11—C12	29.1 (2)
C4—N1—C3—C2	178.65 (12)	N2—C1—C11—C16	−151.79 (14)
C1—C2—C3—N1	0.65 (16)	C2—C1—C11—C12	−151.35 (15)
C1—C2—C3—N3	−176.62 (16)	C2—C1—C11—C16	27.7 (2)
N2—N1—C4—C5	141.21 (14)	C1—C11—C12—C13	179.32 (14)
N2—N1—C4—C9	−36.72 (18)	C16—C11—C12—C13	0.3 (2)
C3—N1—C4—C5	−37.9 (2)	C11—C12—C13—C14	0.0 (3)
C3—N1—C4—C9	144.17 (15)	C12—C13—C14—C15	−0.2 (3)
N1—C4—C5—C6	−178.27 (13)	C13—C14—C15—C16	0.1 (3)
C9—C4—C5—C6	−0.3 (2)	C14—C15—C16—C11	0.1 (3)
C4—C5—C6—C7	2.1 (2)	C1—C11—C16—C15	−179.39 (15)
C10—O—C7—C6	−174.60 (16)	C12—C11—C16—C15	−0.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3NA···N2i	0.89 (2)	2.37 (2)	3.228 (2)	162.5 (16)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3NA⋯N2i	0.89 (2)	2.37 (2)	3.228 (2)	162.5 (16)

Symmetry code: (i) .