N-(2-Bromo-4-methyl-phen-yl)-2-(5-methyl-2-phenyl-pyrazolo-[1,5-a]pyrimidin-7-yl)acetamide.

The fused pyrazole and pyrimidine rings in the title compound, C22H19BrN4O, are almost coplanar, their planes being inclined to one another by 2.08 (13)°. The dihedral angles formed by the mean plane of the fused ring system and the phenyl and benzene rings are 16.21 (4) and 82.84 (4)°, respectively. An intra-molecular N-H⋯N hydrogen bond is observed. In the crystal, mol-ecules form inversion dimers via pairs of C-H⋯O hydrogen bonds. π-π inter-actions, with centroid-centroid distances of 3.4916 (9) Å, connect the dimers into a three-dimensional network.

Related literature

For pharmacological and biochemical properties of pyrazolo­[1,5-a]pyrimidine derivatives, see: Selleri et al. (2005 ▶); Almansa et al. (2001 ▶); Suzuki et al. (2001 ▶); Chen et al. (2004 ▶). For related structures, see: Bassoude et al. (2013a ▶,b ▶).

Experimental

Crystal data

C22H19BrN4O

M = 435.32

Monoclinic,

a = 9.8102 (6) Å

b = 7.2915 (4) Å

c = 27.0162 (14) Å

β = 92.942 (3)°

V = 1929.95 (19) Å3

Z = 4

Mo Kα radiation

μ = 2.15 mm−1

T = 296 K

0.42 × 0.33 × 0.25 mm

Data collection

Bruker X8 APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.739, T max = 0.867

29996 measured reflections

6371 independent reflections

3830 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.107

S = 1.02

6371 reflections

253 parameters

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.62 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; 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, 2012 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813011811/rz5060sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813011811/rz5060Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813011811/rz5060Isup3.cml

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

C22H19BrN4O	F(000) = 888
Mr = 435.32	Dx = 1.498 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6371 reflections
a = 9.8102 (6) Å	θ = 2.5–31.4°
b = 7.2915 (4) Å	µ = 2.15 mm−1
c = 27.0162 (14) Å	T = 296 K
β = 92.942 (3)°	Block, colourless
V = 1929.95 (19) Å3	0.42 × 0.33 × 0.25 mm
Z = 4

Bruker X8 APEXII area-detector diffractometer	6371 independent reflections
Radiation source: fine-focus sealed tube	3830 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.044
φ and ω scans	θmax = 31.4°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −14→14
Tmin = 0.739, Tmax = 0.867	k = −10→10
29996 measured reflections	l = −39→39

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)] = 0.041	Hydrogen site location: difference Fourier map
wR(F2) = 0.107	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0467P)2 + 0.2795P] where P = (Fo2 + 2Fc2)/3
6371 reflections	(Δ/σ)max = 0.001
253 parameters	Δρmax = 0.41 e Å−3
0 restraints	Δρmin = −0.62 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
C1	0.6173 (2)	0.8274 (2)	−0.03898 (7)	0.0377 (4)
H1	0.6836	0.8688	−0.0597	0.045*
C2	0.4907 (2)	0.7594 (2)	−0.05997 (7)	0.0389 (4)
C3	0.41574 (19)	0.7044 (2)	0.01713 (7)	0.0363 (4)
C4	0.3365 (2)	0.6608 (2)	0.05592 (7)	0.0389 (4)
H4	0.2478	0.6155	0.0539	0.047*
C5	0.41646 (19)	0.6987 (2)	0.09908 (7)	0.0345 (4)
C6	0.64217 (19)	0.8324 (2)	0.01096 (7)	0.0329 (4)
C7	0.76984 (19)	0.9055 (2)	0.03730 (7)	0.0366 (4)
H7A	0.7446	0.9745	0.0661	0.044*
H7B	0.8141	0.9894	0.0154	0.044*
C8	0.87117 (19)	0.7571 (2)	0.05392 (7)	0.0330 (4)
C9	0.89437 (18)	0.4831 (2)	0.10641 (7)	0.0332 (4)
C10	0.89659 (19)	0.4341 (2)	0.15591 (7)	0.0361 (4)
C11	0.9568 (2)	0.2718 (3)	0.17291 (8)	0.0422 (5)
H11	0.9557	0.2416	0.2063	0.051*
C12	1.0184 (2)	0.1551 (3)	0.14043 (8)	0.0436 (5)
C13	1.0160 (2)	0.2037 (3)	0.09087 (8)	0.0432 (5)
H13	1.0567	0.1265	0.0685	0.052*
C14	0.9547 (2)	0.3641 (3)	0.07366 (8)	0.0397 (4)
H14	0.9538	0.3925	0.0401	0.048*
C15	1.0869 (3)	−0.0203 (3)	0.15829 (10)	0.0691 (7)
H15A	1.1706	0.0085	0.1766	0.104*
H15B	1.1060	−0.0955	0.1303	0.104*
H15C	1.0274	−0.0854	0.1793	0.104*
C16	0.4645 (2)	0.7598 (3)	−0.11515 (8)	0.0512 (5)
H16C	0.4995	0.8709	−0.1287	0.077*
H16A	0.3680	0.7523	−0.1229	0.077*
H16B	0.5091	0.6563	−0.1292	0.077*
C17	0.38277 (19)	0.6745 (2)	0.15115 (7)	0.0361 (4)
C18	0.2742 (2)	0.5647 (3)	0.16391 (9)	0.0470 (5)
H18	0.2209	0.5064	0.1392	0.056*
C19	0.2447 (2)	0.5415 (3)	0.21290 (9)	0.0541 (6)
H19	0.1721	0.4670	0.2209	0.065*
C20	0.3217 (2)	0.6275 (3)	0.25011 (9)	0.0533 (6)
H20	0.3013	0.6116	0.2831	0.064*
C21	0.4294 (2)	0.7376 (3)	0.23797 (9)	0.0518 (5)
H21	0.4818	0.7966	0.2628	0.062*
C22	0.4595 (2)	0.7604 (3)	0.18897 (8)	0.0452 (5)
H22	0.5326	0.8345	0.1812	0.054*
N1	0.39309 (17)	0.6994 (2)	−0.03282 (6)	0.0405 (4)
N2	0.54163 (15)	0.7640 (2)	0.08894 (6)	0.0338 (3)
N3	0.53930 (15)	0.76798 (18)	0.03862 (6)	0.0317 (3)
N4	0.82608 (16)	0.6428 (2)	0.08896 (6)	0.0370 (4)
H4A	0.7499	0.6695	0.1016	0.044*
O1	0.98349 (14)	0.74725 (19)	0.03713 (5)	0.0453 (3)
Br1	0.81300 (3)	0.58958 (3)	0.201758 (8)	0.05961 (10)

	U11	U22	U33	U12	U13	U23
C1	0.0391 (11)	0.0356 (9)	0.0378 (10)	0.0071 (8)	−0.0030 (9)	0.0039 (8)
C2	0.0459 (12)	0.0288 (8)	0.0409 (11)	0.0120 (8)	−0.0089 (9)	−0.0027 (7)
C3	0.0315 (10)	0.0304 (8)	0.0458 (12)	0.0060 (7)	−0.0103 (9)	−0.0036 (7)
C4	0.0268 (10)	0.0370 (9)	0.0523 (12)	0.0007 (8)	−0.0044 (9)	−0.0031 (8)
C5	0.0282 (10)	0.0278 (8)	0.0473 (11)	0.0048 (7)	−0.0008 (8)	−0.0028 (7)
C6	0.0303 (10)	0.0275 (8)	0.0405 (10)	0.0056 (7)	−0.0035 (8)	0.0011 (7)
C7	0.0330 (10)	0.0341 (9)	0.0420 (11)	0.0014 (8)	−0.0036 (8)	0.0021 (7)
C8	0.0294 (10)	0.0381 (9)	0.0309 (9)	0.0008 (7)	−0.0032 (8)	−0.0041 (7)
C9	0.0223 (9)	0.0400 (9)	0.0371 (10)	0.0042 (7)	−0.0009 (8)	0.0022 (7)
C10	0.0291 (10)	0.0442 (10)	0.0350 (10)	0.0004 (8)	0.0005 (8)	0.0002 (8)
C11	0.0409 (12)	0.0462 (10)	0.0387 (11)	−0.0011 (9)	−0.0055 (9)	0.0086 (8)
C12	0.0366 (11)	0.0381 (9)	0.0549 (13)	0.0032 (8)	−0.0102 (10)	0.0024 (9)
C13	0.0359 (11)	0.0409 (10)	0.0522 (13)	0.0050 (8)	−0.0026 (9)	−0.0077 (9)
C14	0.0345 (11)	0.0466 (10)	0.0377 (11)	0.0048 (8)	−0.0027 (9)	−0.0010 (8)
C15	0.0758 (19)	0.0495 (12)	0.0796 (18)	0.0205 (13)	−0.0183 (15)	0.0084 (12)
C16	0.0619 (15)	0.0482 (11)	0.0422 (12)	0.0110 (10)	−0.0118 (11)	−0.0065 (9)
C17	0.0277 (10)	0.0335 (9)	0.0470 (12)	0.0077 (7)	0.0010 (8)	−0.0020 (8)
C18	0.0373 (12)	0.0483 (11)	0.0551 (13)	−0.0024 (9)	0.0001 (10)	−0.0032 (9)
C19	0.0418 (13)	0.0624 (13)	0.0588 (15)	−0.0058 (11)	0.0085 (11)	0.0066 (11)
C20	0.0467 (14)	0.0681 (14)	0.0455 (13)	0.0084 (11)	0.0074 (11)	0.0030 (10)
C21	0.0453 (13)	0.0632 (13)	0.0466 (13)	−0.0024 (11)	0.0013 (10)	−0.0085 (10)
C22	0.0366 (11)	0.0490 (11)	0.0501 (13)	−0.0034 (9)	0.0015 (10)	−0.0048 (9)
N1	0.0393 (10)	0.0358 (8)	0.0451 (10)	0.0055 (7)	−0.0107 (8)	−0.0041 (7)
N2	0.0292 (8)	0.0355 (7)	0.0362 (9)	0.0033 (6)	−0.0027 (7)	−0.0015 (6)
N3	0.0276 (8)	0.0296 (7)	0.0371 (9)	0.0048 (6)	−0.0056 (7)	−0.0012 (6)
N4	0.0279 (9)	0.0454 (8)	0.0379 (9)	0.0098 (7)	0.0046 (7)	0.0059 (7)
O1	0.0352 (8)	0.0541 (8)	0.0474 (8)	0.0065 (6)	0.0094 (7)	0.0049 (6)
Br1	0.0728 (2)	0.06541 (16)	0.04192 (14)	0.01753 (12)	0.01561 (12)	0.00091 (10)

C1—C6	1.359 (3)	C11—H11	0.9300
C1—C2	1.428 (3)	C12—C13	1.384 (3)
C1—H1	0.9300	C12—C15	1.512 (3)
C2—N1	1.311 (3)	C13—C14	1.385 (3)
C2—C16	1.500 (3)	C13—H13	0.9300
C3—N1	1.357 (2)	C14—H14	0.9300
C3—C4	1.374 (3)	C15—H15A	0.9600
C3—N3	1.396 (2)	C15—H15B	0.9600
C4—C5	1.399 (3)	C15—H15C	0.9600
C4—H4	0.9300	C16—H16C	0.9600
C5—N2	1.358 (2)	C16—H16A	0.9600
C5—C17	1.472 (3)	C16—H16B	0.9600
C6—N3	1.369 (2)	C17—C22	1.387 (3)
C6—C7	1.506 (3)	C17—C18	1.390 (3)
C7—C8	1.521 (2)	C18—C19	1.380 (3)
C7—H7A	0.9700	C18—H18	0.9300
C7—H7B	0.9700	C19—C20	1.377 (3)
C8—O1	1.215 (2)	C19—H19	0.9300
C8—N4	1.353 (2)	C20—C21	1.380 (3)
C9—C10	1.383 (3)	C20—H20	0.9300
C9—C14	1.393 (3)	C21—C22	1.381 (3)
C9—N4	1.412 (2)	C21—H21	0.9300
C10—C11	1.390 (3)	C22—H22	0.9300
C10—Br1	1.8962 (19)	N2—N3	1.359 (2)
C11—C12	1.384 (3)	N4—H4A	0.8600
C6—C1—C2	120.76 (19)	C13—C14—C9	120.30 (19)
C6—C1—H1	119.6	C13—C14—H14	119.8
C2—C1—H1	119.6	C9—C14—H14	119.8
N1—C2—C1	122.65 (18)	C12—C15—H15A	109.5
N1—C2—C16	117.63 (19)	C12—C15—H15B	109.5
C1—C2—C16	119.7 (2)	H15A—C15—H15B	109.5
N1—C3—C4	133.01 (18)	C12—C15—H15C	109.5
N1—C3—N3	121.12 (18)	H15A—C15—H15C	109.5
C4—C3—N3	105.85 (16)	H15B—C15—H15C	109.5
C3—C4—C5	105.95 (17)	C2—C16—H16C	109.5
C3—C4—H4	127.0	C2—C16—H16A	109.5
C5—C4—H4	127.0	H16C—C16—H16A	109.5
N2—C5—C4	112.04 (17)	C2—C16—H16B	109.5
N2—C5—C17	118.99 (17)	H16C—C16—H16B	109.5
C4—C5—C17	128.97 (18)	H16A—C16—H16B	109.5
C1—C6—N3	115.66 (17)	C22—C17—C18	118.12 (19)
C1—C6—C7	125.52 (18)	C22—C17—C5	120.65 (18)
N3—C6—C7	118.81 (16)	C18—C17—C5	121.24 (18)
C6—C7—C8	113.78 (14)	C19—C18—C17	120.7 (2)
C6—C7—H7A	108.8	C19—C18—H18	119.7
C8—C7—H7A	108.8	C17—C18—H18	119.7
C6—C7—H7B	108.8	C20—C19—C18	120.7 (2)
C8—C7—H7B	108.8	C20—C19—H19	119.7
H7A—C7—H7B	107.7	C18—C19—H19	119.7
O1—C8—N4	124.06 (17)	C19—C20—C21	119.3 (2)
O1—C8—C7	121.57 (17)	C19—C20—H20	120.4
N4—C8—C7	114.36 (16)	C21—C20—H20	120.4
C10—C9—C14	117.85 (17)	C20—C21—C22	120.1 (2)
C10—C9—N4	121.28 (16)	C20—C21—H21	119.9
C14—C9—N4	120.76 (17)	C22—C21—H21	119.9
C9—C10—C11	121.64 (18)	C21—C22—C17	121.1 (2)
C9—C10—Br1	119.42 (14)	C21—C22—H22	119.4
C11—C10—Br1	118.93 (15)	C17—C22—H22	119.4
C12—C11—C10	120.42 (19)	C2—N1—C3	117.42 (17)
C12—C11—H11	119.8	C5—N2—N3	103.92 (14)
C10—C11—H11	119.8	N2—N3—C6	125.34 (15)
C11—C12—C13	118.01 (18)	N2—N3—C3	112.24 (15)
C11—C12—C15	121.3 (2)	C6—N3—C3	122.38 (16)
C13—C12—C15	120.7 (2)	C8—N4—C9	125.11 (15)
C12—C13—C14	121.77 (19)	C8—N4—H4A	117.4
C12—C13—H13	119.1	C9—N4—H4A	117.4
C14—C13—H13	119.1

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···N2	0.86	2.17	2.927 (2)	147
C14—H14···O1i	0.93	2.43	3.189 (2)	139

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4A⋯N2	0.86	2.17	2.927 (2)	147
C14—H14⋯O1i	0.93	2.43	3.189 (2)	139

Symmetry code: (i) .