N-(5-Phenyl-1H-pyrazol-3-yl)benzene-1,2-diamine.

In the title compound, C(15)H(14)N(4), the phenyl and pyrazole rings are essentially coplanar, being twisted relative to each other by a dihedral of only 3.68 (11)°. The benzene ring makes a dihedral angle of 64.47 (11)° with the pyrazole ring. The crystal structure is stabilized by two inter-molecular N-H⋯N hydrogen-bonds, which build a two-dimensional network developing parallel to (100). An intra-molecular N-H⋯N hydrogen bond also occurs.

Related literature

For the pharmacological applications of N-(3-phenyl-1H-pyrazol-5-yl)benzene-1, 2-diamine, see: Sharon et al. (2005 ▶); Barsoum et al. (2006 ▶); Cunico et al. (2006 ▶). For the use of pyrazole derivatives as chelating agents, see: Onishi et al. (2006 ▶) and as corrosion inibitors, see: Tebbji et al. (2005 ▶).

Experimental

Crystal data

C15H14N4

M = 250.30

Monoclinic,

a = 13.2357 (8) Å

b = 5.8473 (4) Å

c = 16.4039 (10) Å

β = 92.074 (4)°

V = 1268.72 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 298 K

0.32 × 0.27 × 0.19 mm

Data collection

Bruker X8 APEXII CCD area-detector diffractometer

11640 measured reflections

2333 independent reflections

1527 reflections with I > 2σ(I)

R int = 0.056

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.127

S = 1.02

2333 reflections

228 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.15 e Å−3

Δρmin = −0.15 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT (Bruker, 2005 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810009104/dn2548sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810009104/dn2548Isup2.hkl

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

C15H14N4	F(000) = 528
Mr = 250.30	Dx = 1.310 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -p 2ybc	Cell parameters from 12462 reflections
a = 13.2357 (8) Å	θ = 25.4–2.5°
b = 5.8473 (4) Å	µ = 0.08 mm−1
c = 16.4039 (10) Å	T = 298 K
β = 92.074 (4)°	Parallelepiped, clear pale yellow
V = 1268.72 (14) Å3	0.32 × 0.27 × 0.19 mm
Z = 4

Bruker X8 APEX CCD area-detector diffractometer	1527 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.056
graphite	θmax = 25.4°, θmin = 2.5°
φ and ω scans	h = −15→15
11640 measured reflections	k = −7→6
2333 independent reflections	l = −19→19

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0719P)2] where P = (Fo2 + 2Fc2)/3
2333 reflections	(Δ/σ)max < 0.001
228 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.15 e Å−3

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 > 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
N1	0.92397 (12)	0.5307 (3)	0.69736 (9)	0.0414 (4)
N2	1.00286 (12)	0.6719 (3)	0.67931 (9)	0.0423 (4)
N3	1.01564 (13)	1.0130 (3)	0.60311 (9)	0.0426 (4)
N4	1.10392 (16)	0.6520 (3)	0.51288 (11)	0.0507 (5)
C1	0.95922 (14)	0.8361 (3)	0.63347 (10)	0.0369 (5)
C2	0.85506 (15)	0.8033 (4)	0.62309 (11)	0.0416 (5)
C3	0.83439 (14)	0.6054 (3)	0.66539 (10)	0.0385 (5)
C4	0.73944 (15)	0.4805 (4)	0.67390 (11)	0.0421 (5)
C5	0.73429 (19)	0.2767 (4)	0.71726 (13)	0.0541 (6)
C6	0.6440 (2)	0.1608 (5)	0.72155 (16)	0.0669 (7)
C7	0.55732 (19)	0.2441 (5)	0.68386 (16)	0.0684 (7)
C8	0.56061 (19)	0.4460 (5)	0.64097 (17)	0.0695 (7)
C9	0.65081 (17)	0.5631 (5)	0.63635 (14)	0.0576 (6)
C10	1.12135 (15)	1.0028 (3)	0.59179 (10)	0.0396 (5)
C11	1.16551 (15)	0.8230 (3)	0.54840 (11)	0.0424 (5)
C12	1.26837 (18)	0.8308 (5)	0.53560 (13)	0.0561 (6)
C13	1.32666 (19)	1.0142 (5)	0.56121 (15)	0.0662 (7)
C14	1.2833 (2)	1.1923 (5)	0.60222 (14)	0.0619 (7)
C15	1.18167 (18)	1.1845 (4)	0.61841 (12)	0.0498 (6)
H15	1.1477 (16)	1.308 (4)	0.6454 (13)	0.056 (6)*
H1	0.9384 (19)	0.389 (4)	0.7256 (16)	0.083 (8)*
H2	0.8072 (16)	0.894 (4)	0.5930 (13)	0.054 (6)*
H3	0.9810 (18)	1.130 (4)	0.5814 (15)	0.070 (8)*
H4A	1.1389 (18)	0.521 (5)	0.4963 (15)	0.073 (8)*
H4B	1.052 (2)	0.591 (5)	0.5453 (18)	0.092 (9)*
H5	0.7973 (19)	0.217 (4)	0.7414 (15)	0.075 (7)*
H6	0.6439 (18)	0.011 (5)	0.7494 (16)	0.082 (8)*
H7	0.4918 (19)	0.165 (4)	0.6883 (15)	0.074 (7)*
H8	0.498 (2)	0.513 (4)	0.6133 (16)	0.089 (8)*
H9	0.6532 (19)	0.707 (5)	0.6077 (16)	0.082 (8)*
H12	1.2969 (19)	0.700 (4)	0.5093 (15)	0.074 (8)*
H13	1.4002 (19)	1.025 (4)	0.5512 (15)	0.074 (7)*
H14	1.3233 (18)	1.322 (4)	0.6203 (14)	0.067 (7)*

	U11	U22	U33	U12	U13	U23
N1	0.0454 (10)	0.0454 (11)	0.0333 (8)	−0.0028 (8)	−0.0006 (7)	0.0066 (8)
N2	0.0474 (10)	0.0455 (11)	0.0338 (8)	−0.0027 (8)	−0.0025 (7)	0.0044 (7)
N3	0.0481 (11)	0.0403 (11)	0.0392 (9)	0.0005 (9)	0.0011 (7)	0.0042 (8)
N4	0.0659 (13)	0.0445 (12)	0.0418 (10)	−0.0001 (11)	0.0015 (9)	−0.0055 (8)
C1	0.0472 (12)	0.0379 (12)	0.0255 (9)	−0.0001 (9)	0.0006 (7)	−0.0004 (8)
C2	0.0474 (13)	0.0451 (13)	0.0320 (9)	0.0064 (10)	−0.0016 (8)	0.0016 (9)
C3	0.0431 (11)	0.0461 (13)	0.0261 (9)	0.0016 (9)	−0.0008 (8)	−0.0016 (8)
C4	0.0469 (12)	0.0469 (14)	0.0326 (9)	−0.0004 (10)	0.0021 (8)	−0.0056 (9)
C5	0.0567 (15)	0.0555 (16)	0.0498 (12)	−0.0048 (12)	−0.0028 (10)	0.0050 (11)
C6	0.0655 (17)	0.0678 (19)	0.0673 (16)	−0.0164 (14)	0.0007 (13)	0.0101 (14)
C7	0.0525 (16)	0.082 (2)	0.0707 (16)	−0.0185 (15)	0.0025 (12)	0.0020 (14)
C8	0.0454 (15)	0.088 (2)	0.0750 (17)	−0.0034 (14)	−0.0012 (12)	0.0110 (15)
C9	0.0491 (14)	0.0641 (17)	0.0593 (14)	0.0001 (12)	−0.0010 (10)	0.0074 (13)
C10	0.0480 (12)	0.0425 (13)	0.0280 (9)	−0.0022 (10)	−0.0028 (8)	0.0044 (8)
C11	0.0518 (13)	0.0447 (13)	0.0305 (9)	−0.0017 (10)	−0.0018 (8)	0.0053 (9)
C12	0.0562 (15)	0.0675 (17)	0.0447 (12)	0.0069 (14)	0.0018 (10)	0.0055 (12)
C13	0.0498 (15)	0.090 (2)	0.0590 (15)	−0.0070 (15)	−0.0007 (12)	0.0108 (14)
C14	0.0614 (16)	0.0685 (19)	0.0551 (14)	−0.0175 (15)	−0.0079 (12)	0.0046 (13)
C15	0.0586 (15)	0.0505 (15)	0.0400 (11)	−0.0076 (12)	−0.0035 (10)	0.0028 (10)

N1—C3	1.352 (2)	C6—C7	1.372 (4)
N1—N2	1.372 (2)	C6—H6	0.99 (3)
N1—H1	0.96 (3)	C7—C8	1.376 (4)
N2—C1	1.338 (2)	C7—H7	0.99 (2)
N3—C1	1.379 (2)	C8—C9	1.381 (3)
N3—C10	1.419 (2)	C8—H8	1.01 (3)
N3—H3	0.89 (2)	C9—H9	0.96 (3)
N4—C11	1.404 (3)	C10—C15	1.390 (3)
N4—H4A	0.94 (3)	C10—C11	1.408 (3)
N4—H4B	0.96 (3)	C11—C12	1.386 (3)
C1—C2	1.396 (3)	C12—C13	1.378 (4)
C2—C3	1.382 (3)	C12—H12	0.96 (2)
C2—H2	0.95 (2)	C13—C14	1.376 (4)
C3—C4	1.465 (3)	C13—H13	1.00 (2)
C4—C5	1.391 (3)	C14—C15	1.382 (3)
C4—C9	1.392 (3)	C14—H14	0.97 (3)
C5—C6	1.378 (3)	C15—H15	0.96 (2)
C5—H5	0.97 (3)
C3—N1—N2	112.68 (17)	C6—C7—C8	119.6 (3)
C3—N1—H1	128.2 (16)	C6—C7—H7	121.5 (14)
N2—N1—H1	118.8 (15)	C8—C7—H7	118.9 (14)
C1—N2—N1	103.70 (15)	C7—C8—C9	119.8 (2)
C1—N3—C10	124.40 (17)	C7—C8—H8	121.6 (15)
C1—N3—H3	116.4 (15)	C9—C8—H8	118.6 (15)
C10—N3—H3	118.3 (15)	C8—C9—C4	121.3 (2)
C11—N4—H4A	114.5 (15)	C8—C9—H9	120.2 (15)
C11—N4—H4B	117.1 (16)	C4—C9—H9	118.4 (15)
H4A—N4—H4B	103 (2)	C15—C10—C11	119.0 (2)
N2—C1—N3	120.85 (17)	C15—C10—N3	118.98 (19)
N2—C1—C2	111.97 (17)	C11—C10—N3	121.78 (17)
N3—C1—C2	127.18 (18)	C12—C11—N4	121.3 (2)
C3—C2—C1	105.46 (17)	C12—C11—C10	118.7 (2)
C3—C2—H2	125.9 (13)	N4—C11—C10	119.76 (19)
C1—C2—H2	128.6 (13)	C13—C12—C11	121.5 (2)
N1—C3—C2	106.18 (18)	C13—C12—H12	122.1 (15)
N1—C3—C4	123.06 (18)	C11—C12—H12	116.4 (15)
C2—C3—C4	130.67 (18)	C14—C13—C12	120.0 (2)
C5—C4—C9	117.9 (2)	C14—C13—H13	117.3 (14)
C5—C4—C3	122.29 (19)	C12—C13—H13	122.7 (14)
C9—C4—C3	119.8 (2)	C13—C14—C15	119.7 (3)
C6—C5—C4	120.4 (2)	C13—C14—H14	120.9 (14)
C6—C5—H5	122.4 (15)	C15—C14—H14	119.5 (14)
C4—C5—H5	117.2 (15)	C14—C15—C10	121.1 (2)
C7—C6—C5	121.0 (3)	C14—C15—H15	122.5 (13)
C7—C6—H6	120.6 (15)	C10—C15—H15	116.3 (13)
C5—C6—H6	118.3 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N2i	0.97 (2)	2.14 (3)	3.048 (2)	157 (2)
N3—H3···N4ii	0.89 (2)	2.27 (2)	3.122 (2)	160 (2)
N4—H4B···N2	0.95 (3)	2.36 (3)	3.086 (2)	132 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N2i	0.97 (2)	2.14 (3)	3.048 (2)	157 (2)
N3—H3⋯N4ii	0.89 (2)	2.27 (2)	3.122 (2)	160 (2)
N4—H4B⋯N2	0.95 (3)	2.36 (3)	3.086 (2)	132 (2)

Symmetry codes: (i) ; (ii) .