1-[(6-Chloro-3-pyrid-yl)meth-yl]-N-(4-ethoxy-phen-yl)-3-phenyl-1H-pyrazole-5-carboxamide.

In the title compound, C(24)H(21)ClN(4)O(2), the pyrazole ring makes dihedral angles of 7.70 (11), 89.17 (11) and 40.68 (11)° with the phenyl, pyridine and ethoxy-phenyl rings, respectively. There are some intra-molecular C-H⋯O and C-H⋯π bonds giving rigidity to the mol-ecule, while weak inter-molecular N-H⋯N and C-H⋯π hydrogen bonds link the mol-ecules into a two-dimensional structure.

Related literature

For the biological properties of pyrazole derivatives, see: Jia et al. (2004 ▶); Wei et al. (2006 ▶); Xia et al. (2007 ▶). For the synthesis and bioactivity evaluation of pyrazole derivatives, see: Zhang et al. (2008 ▶); Zhao et al. (2008 ▶); Tang et al. (2007 ▶).

Experimental

Crystal data

C24H21ClN4O2

M = 432.90

Monoclinic,

a = 10.0697 (12) Å

b = 5.1399 (6) Å

c = 40.990 (5) Å

β = 96.446 (2)°

V = 2108.1 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.21 mm−1

T = 298 K

0.15 × 0.12 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.96, T max = 0.98

10472 measured reflections

3699 independent reflections

2571 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.104

S = 1.03

3699 reflections

280 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.23 e Å−3

Data collection: SMART (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809010290/bg2246sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809010290/bg2246Isup2.hkl

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

C24H21ClN4O2	F(000) = 904
Mr = 432.90	Dx = 1.364 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2064 reflections
a = 10.0697 (12) Å	θ = 2.7–22.1°
b = 5.1399 (6) Å	µ = 0.21 mm−1
c = 40.990 (5) Å	T = 298 K
β = 96.446 (2)°	Block, colourless
V = 2108.1 (4) Å3	0.15 × 0.12 × 0.10 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3699 independent reflections
Radiation source: fine-focus sealed tube	2571 reflections with I > 2σ(I)
graphite	Rint = 0.031
φ and ω scans	θmax = 25.0°, θmin = 1.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −9→11
Tmin = 0.96, Tmax = 0.98	k = −6→6
10472 measured reflections	l = −46→48

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0455P)2 + 0.3478P] where P = (Fo2 + 2Fc2)/3
3699 reflections	(Δ/σ)max < 0.001
280 parameters	Δρmax = 0.14 e Å−3
0 restraints	Δρmin = −0.22 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
Cl1	0.71782 (6)	−0.22109 (13)	0.164051 (17)	0.0697 (2)
O1	0.10720 (14)	0.0159 (3)	0.08714 (4)	0.0596 (4)
O2	−0.32793 (14)	−0.7133 (3)	0.00202 (4)	0.0592 (4)
N1	0.15163 (15)	0.5760 (3)	0.16155 (4)	0.0401 (4)
N2	0.14531 (15)	0.4370 (3)	0.13344 (4)	0.0382 (4)
N3	0.60325 (16)	0.1539 (4)	0.12864 (4)	0.0478 (5)
N4	−0.10977 (15)	−0.0112 (3)	0.09696 (4)	0.0453 (4)
H4	−0.1670	0.0486	0.1091	0.054*
C1	0.04487 (18)	0.5012 (4)	0.17605 (5)	0.0384 (5)
C2	−0.02871 (19)	0.3133 (4)	0.15696 (5)	0.0420 (5)
H2	−0.1070	0.2322	0.1616	0.050*
C3	0.03779 (18)	0.2730 (4)	0.13003 (5)	0.0381 (5)
C4	0.02032 (19)	0.6110 (4)	0.20807 (5)	0.0395 (5)
C5	−0.0794 (2)	0.5097 (4)	0.22505 (5)	0.0509 (6)
H5	−0.1304	0.3704	0.2162	0.061*
C6	−0.1040 (2)	0.6129 (5)	0.25494 (6)	0.0621 (7)
H6	−0.1718	0.5436	0.2659	0.075*
C7	−0.0295 (3)	0.8158 (5)	0.26846 (6)	0.0660 (7)
H7	−0.0462	0.8846	0.2886	0.079*
C8	0.0708 (3)	0.9179 (5)	0.25205 (6)	0.0695 (7)
H8	0.1224	1.0551	0.2612	0.083*
C9	0.0951 (2)	0.8179 (4)	0.22210 (5)	0.0545 (6)
H9	0.1624	0.8897	0.2111	0.065*
C10	0.25901 (18)	0.4539 (4)	0.11441 (5)	0.0409 (5)
H10A	0.2898	0.6327	0.1143	0.049*
H10B	0.2309	0.4033	0.0919	0.049*
C11	0.37272 (18)	0.2810 (4)	0.12835 (4)	0.0354 (5)
C12	0.3565 (2)	0.0878 (4)	0.15098 (5)	0.0452 (5)
H12	0.2738	0.0643	0.1586	0.054*
C13	0.4616 (2)	−0.0693 (4)	0.16222 (5)	0.0499 (6)
H13	0.4518	−0.2001	0.1774	0.060*
C14	0.58170 (19)	−0.0273 (4)	0.15031 (5)	0.0435 (5)
C15	0.4985 (2)	0.3043 (4)	0.11817 (5)	0.0457 (5)
H15	0.5112	0.4336	0.1030	0.055*
C16	0.01583 (19)	0.0825 (4)	0.10273 (5)	0.0413 (5)
C17	−0.15751 (19)	−0.1981 (4)	0.07291 (5)	0.0417 (5)
C18	−0.0756 (2)	−0.3663 (4)	0.05794 (5)	0.0464 (5)
H18	0.0164	−0.3612	0.0637	0.056*
C19	−0.1289 (2)	−0.5423 (4)	0.03440 (5)	0.0486 (5)
H19	−0.0725	−0.6532	0.0245	0.058*
C20	−0.2651 (2)	−0.5540 (4)	0.02558 (5)	0.0462 (5)
C21	−0.3474 (2)	−0.3877 (5)	0.04087 (5)	0.0540 (6)
H21	−0.4395	−0.3950	0.0353	0.065*
C22	−0.2944 (2)	−0.2126 (4)	0.06405 (5)	0.0521 (6)
H22	−0.3511	−0.1021	0.0740	0.062*
C23	−0.2494 (2)	−0.8951 (5)	−0.01383 (6)	0.0588 (6)
H23A	−0.2020	−1.0104	0.0022	0.071*
H23B	−0.1844	−0.8044	−0.0254	0.071*
C24	−0.3440 (3)	−1.0481 (6)	−0.03759 (6)	0.0780 (8)
H24A	−0.4154	−1.1156	−0.0264	0.117*
H24B	−0.2969	−1.1896	−0.0463	0.117*
H24C	−0.3802	−0.9367	−0.0552	0.117*

	U11	U22	U33	U12	U13	U23
Cl1	0.0448 (3)	0.0661 (4)	0.0967 (5)	0.0083 (3)	0.0017 (3)	0.0136 (4)
O1	0.0435 (9)	0.0673 (11)	0.0702 (11)	−0.0103 (8)	0.0162 (8)	−0.0280 (9)
O2	0.0513 (9)	0.0624 (10)	0.0624 (10)	−0.0076 (8)	0.0004 (7)	−0.0262 (8)
N1	0.0388 (9)	0.0392 (10)	0.0424 (10)	−0.0022 (8)	0.0045 (7)	−0.0058 (8)
N2	0.0367 (9)	0.0396 (10)	0.0387 (9)	−0.0042 (8)	0.0063 (7)	−0.0059 (8)
N3	0.0407 (10)	0.0492 (11)	0.0549 (11)	−0.0024 (9)	0.0119 (8)	−0.0025 (9)
N4	0.0378 (9)	0.0557 (11)	0.0430 (10)	−0.0096 (8)	0.0068 (7)	−0.0140 (9)
C1	0.0320 (10)	0.0398 (12)	0.0431 (12)	0.0012 (9)	0.0028 (9)	−0.0005 (10)
C2	0.0333 (11)	0.0481 (13)	0.0446 (12)	−0.0057 (10)	0.0043 (9)	−0.0059 (10)
C3	0.0320 (10)	0.0415 (12)	0.0403 (11)	−0.0030 (9)	0.0013 (9)	−0.0033 (9)
C4	0.0369 (11)	0.0400 (12)	0.0408 (11)	0.0063 (9)	0.0011 (9)	−0.0026 (9)
C5	0.0520 (13)	0.0550 (14)	0.0461 (13)	−0.0029 (11)	0.0076 (10)	−0.0045 (11)
C6	0.0677 (16)	0.0717 (17)	0.0502 (14)	0.0057 (14)	0.0210 (12)	0.0006 (13)
C7	0.0872 (19)	0.0653 (17)	0.0466 (14)	0.0106 (15)	0.0123 (13)	−0.0111 (13)
C8	0.0876 (19)	0.0611 (17)	0.0595 (16)	−0.0088 (15)	0.0065 (14)	−0.0214 (13)
C9	0.0589 (14)	0.0545 (15)	0.0510 (14)	−0.0081 (12)	0.0104 (11)	−0.0106 (12)
C10	0.0406 (11)	0.0427 (12)	0.0406 (12)	−0.0054 (10)	0.0101 (9)	−0.0014 (10)
C11	0.0357 (11)	0.0351 (11)	0.0359 (11)	−0.0049 (9)	0.0057 (8)	−0.0059 (9)
C12	0.0369 (12)	0.0518 (14)	0.0479 (12)	−0.0053 (10)	0.0095 (9)	0.0053 (11)
C13	0.0469 (13)	0.0509 (14)	0.0517 (13)	−0.0037 (11)	0.0048 (10)	0.0130 (11)
C14	0.0351 (11)	0.0435 (13)	0.0508 (13)	−0.0016 (9)	0.0006 (9)	−0.0057 (11)
C15	0.0461 (13)	0.0454 (13)	0.0471 (13)	−0.0039 (10)	0.0129 (10)	0.0043 (10)
C16	0.0391 (12)	0.0418 (12)	0.0427 (12)	−0.0047 (10)	0.0032 (9)	−0.0041 (10)
C17	0.0436 (12)	0.0447 (13)	0.0366 (11)	−0.0090 (10)	0.0032 (9)	−0.0046 (10)
C18	0.0388 (12)	0.0456 (13)	0.0528 (13)	−0.0020 (10)	−0.0040 (10)	−0.0053 (11)
C19	0.0488 (13)	0.0446 (13)	0.0520 (13)	0.0016 (11)	0.0034 (10)	−0.0096 (11)
C20	0.0485 (13)	0.0457 (13)	0.0437 (12)	−0.0117 (11)	0.0019 (10)	−0.0092 (10)
C21	0.0366 (12)	0.0693 (16)	0.0562 (14)	−0.0104 (11)	0.0048 (10)	−0.0195 (12)
C22	0.0412 (12)	0.0626 (15)	0.0536 (14)	−0.0070 (11)	0.0105 (10)	−0.0195 (12)
C23	0.0591 (14)	0.0627 (16)	0.0562 (14)	−0.0098 (13)	0.0135 (11)	−0.0187 (12)
C24	0.0737 (17)	0.092 (2)	0.0695 (17)	−0.0161 (16)	0.0130 (13)	−0.0413 (16)

Cl1—C14	1.736 (2)	C9—H9	0.9300
O1—C16	1.226 (2)	C10—C11	1.510 (3)
O2—C20	1.366 (2)	C10—H10A	0.9700
O2—C23	1.427 (2)	C10—H10B	0.9700
N1—C1	1.342 (2)	C11—C12	1.381 (3)
N1—N2	1.351 (2)	C11—C15	1.382 (3)
N2—C3	1.367 (2)	C12—C13	1.369 (3)
N2—C10	1.458 (2)	C12—H12	0.9300
N3—C14	1.322 (3)	C13—C14	1.371 (3)
N3—C15	1.339 (3)	C13—H13	0.9300
N4—C16	1.349 (2)	C15—H15	0.9300
N4—C17	1.421 (2)	C17—C18	1.385 (3)
N4—H4	0.8600	C17—C22	1.388 (3)
C1—C2	1.401 (3)	C18—C19	1.386 (3)
C1—C4	1.475 (3)	C18—H18	0.9300
C2—C3	1.370 (3)	C19—C20	1.379 (3)
C2—H2	0.9300	C19—H19	0.9300
C3—C16	1.485 (3)	C20—C21	1.388 (3)
C4—C5	1.386 (3)	C21—C22	1.372 (3)
C4—C9	1.390 (3)	C21—H21	0.9300
C5—C6	1.383 (3)	C22—H22	0.9300
C5—H5	0.9300	C23—C24	1.506 (3)
C6—C7	1.365 (3)	C23—H23A	0.9700
C6—H6	0.9300	C23—H23B	0.9700
C7—C8	1.379 (3)	C24—H24A	0.9600
C7—H7	0.9300	C24—H24B	0.9600
C8—C9	1.378 (3)	C24—H24C	0.9600
C8—H8	0.9300
C20—O2—C23	118.55 (17)	C13—C12—C11	120.33 (18)
C1—N1—N2	105.24 (15)	C13—C12—H12	119.8
N1—N2—C3	111.98 (14)	C11—C12—H12	119.8
N1—N2—C10	117.37 (15)	C12—C13—C14	117.8 (2)
C3—N2—C10	129.97 (16)	C12—C13—H13	121.1
C14—N3—C15	116.06 (17)	C14—C13—H13	121.1
C16—N4—C17	126.88 (17)	N3—C14—C13	124.61 (19)
C16—N4—H4	116.6	N3—C14—Cl1	116.05 (15)
C17—N4—H4	116.6	C13—C14—Cl1	119.34 (17)
N1—C1—C2	110.48 (17)	N3—C15—C11	124.67 (19)
N1—C1—C4	120.47 (17)	N3—C15—H15	117.7
C2—C1—C4	129.03 (17)	C11—C15—H15	117.7
C3—C2—C1	106.18 (17)	O1—C16—N4	123.54 (18)
C3—C2—H2	126.9	O1—C16—C3	121.32 (17)
C1—C2—H2	126.9	N4—C16—C3	115.13 (17)
N2—C3—C2	106.11 (16)	C18—C17—C22	118.31 (19)
N2—C3—C16	122.22 (16)	C18—C17—N4	123.88 (18)
C2—C3—C16	131.48 (17)	C22—C17—N4	117.81 (18)
C5—C4—C9	117.98 (19)	C17—C18—C19	120.80 (19)
C5—C4—C1	120.42 (18)	C17—C18—H18	119.6
C9—C4—C1	121.61 (18)	C19—C18—H18	119.6
C6—C5—C4	120.8 (2)	C20—C19—C18	120.46 (19)
C6—C5—H5	119.6	C20—C19—H19	119.8
C4—C5—H5	119.6	C18—C19—H19	119.8
C7—C6—C5	120.5 (2)	O2—C20—C19	125.40 (19)
C7—C6—H6	119.7	O2—C20—C21	115.80 (18)
C5—C6—H6	119.7	C19—C20—C21	118.78 (19)
C6—C7—C8	119.5 (2)	C22—C21—C20	120.72 (19)
C6—C7—H7	120.3	C22—C21—H21	119.6
C8—C7—H7	120.3	C20—C21—H21	119.6
C9—C8—C7	120.4 (2)	C21—C22—C17	120.9 (2)
C9—C8—H8	119.8	C21—C22—H22	119.5
C7—C8—H8	119.8	C17—C22—H22	119.5
C8—C9—C4	120.8 (2)	O2—C23—C24	107.08 (19)
C8—C9—H9	119.6	O2—C23—H23A	110.3
C4—C9—H9	119.6	C24—C23—H23A	110.3
N2—C10—C11	111.72 (16)	O2—C23—H23B	110.3
N2—C10—H10A	109.3	C24—C23—H23B	110.3
C11—C10—H10A	109.3	H23A—C23—H23B	108.6
N2—C10—H10B	109.3	C23—C24—H24A	109.5
C11—C10—H10B	109.3	C23—C24—H24B	109.5
H10A—C10—H10B	107.9	H24A—C24—H24B	109.5
C12—C11—C15	116.50 (18)	C23—C24—H24C	109.5
C12—C11—C10	122.38 (16)	H24A—C24—H24C	109.5
C15—C11—C10	121.09 (18)	H24B—C24—H24C	109.5
C1—N1—N2—C3	−0.8 (2)	C11—C12—C13—C14	0.1 (3)
C1—N1—N2—C10	−172.37 (16)	C15—N3—C14—C13	0.2 (3)
N2—N1—C1—C2	0.2 (2)	C15—N3—C14—Cl1	−179.67 (15)
N2—N1—C1—C4	178.97 (16)	C12—C13—C14—N3	−0.2 (3)
N1—C1—C2—C3	0.5 (2)	C12—C13—C14—Cl1	179.70 (16)
C4—C1—C2—C3	−178.14 (19)	C14—N3—C15—C11	−0.2 (3)
N1—N2—C3—C2	1.2 (2)	C12—C11—C15—N3	0.1 (3)
C10—N2—C3—C2	171.32 (18)	C10—C11—C15—N3	−178.05 (18)
N1—N2—C3—C16	−174.30 (17)	C17—N4—C16—O1	0.5 (3)
C10—N2—C3—C16	−4.1 (3)	C17—N4—C16—C3	−178.72 (18)
C1—C2—C3—N2	−1.0 (2)	N2—C3—C16—O1	18.9 (3)
C1—C2—C3—C16	173.9 (2)	C2—C3—C16—O1	−155.2 (2)
N1—C1—C4—C5	−171.48 (18)	N2—C3—C16—N4	−161.82 (18)
C2—C1—C4—C5	7.0 (3)	C2—C3—C16—N4	24.0 (3)
N1—C1—C4—C9	8.7 (3)	C16—N4—C17—C18	19.0 (3)
C2—C1—C4—C9	−172.8 (2)	C16—N4—C17—C22	−161.1 (2)
C9—C4—C5—C6	0.4 (3)	C22—C17—C18—C19	0.8 (3)
C1—C4—C5—C6	−179.4 (2)	N4—C17—C18—C19	−179.33 (19)
C4—C5—C6—C7	−0.6 (4)	C17—C18—C19—C20	−0.4 (3)
C5—C6—C7—C8	0.1 (4)	C23—O2—C20—C19	3.9 (3)
C6—C7—C8—C9	0.6 (4)	C23—O2—C20—C21	−177.9 (2)
C7—C8—C9—C4	−0.7 (4)	C18—C19—C20—O2	177.8 (2)
C5—C4—C9—C8	0.2 (3)	C18—C19—C20—C21	−0.4 (3)
C1—C4—C9—C8	−180.0 (2)	O2—C20—C21—C22	−177.6 (2)
N1—N2—C10—C11	80.0 (2)	C19—C20—C21—C22	0.8 (3)
C3—N2—C10—C11	−89.7 (2)	C20—C21—C22—C17	−0.3 (4)
N2—C10—C11—C12	14.6 (3)	C18—C17—C22—C21	−0.5 (3)
N2—C10—C11—C15	−167.36 (17)	N4—C17—C22—C21	179.7 (2)
C15—C11—C12—C13	0.0 (3)	C20—O2—C23—C24	178.38 (19)
C10—C11—C12—C13	178.07 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10B···O1	0.97	2.35	2.876 (3)	114
C18—H18···O1	0.93	2.31	2.861 (3)	118
C12—H12···Cg1	0.93	2.74	3.354 (2)	125
N4—H4···N3i	0.86	2.59	3.406 (2)	159
C23—H23A···Cg2ii	0.97	2.71	3.571 (3)	149

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10B⋯O1	0.97	2.35	2.876 (3)	114
C18—H18⋯O1	0.93	2.31	2.861 (3)	118
C12—H12⋯Cg1	0.93	2.74	3.354 (2)	125
N4—H4⋯N3i	0.86	2.59	3.406 (2)	159
C23—H23A⋯Cg2ii	0.97	2.71	3.571 (3)	149

Symmetry codes: (i) ; (ii) . Cg1 and Cg2 are the centroids of the N1/N2/C1–C3 and C17–C22 rings, respectively.