(±)-3-(5-Amino-3-methyl-1-phenyl-1H-pyrazol-4-yl)-2-benzo-furan-1(3H)-one.

In the title compound, C18H15N3O2, the benzo-furan ring system is essentially planar, the rings making a dihedral angle of 0.57 (9)°. The phenyl, furan and benzene rings subtend dihedral angles of 47.07 (10), 85.76 (7) and 86.04 (7)°, respectively, with the pyrazole ring. In the crystal, mol-ecules are linked by weak N-H⋯N, N-H⋯O and C-H⋯O inter-actions, generating edge-fused R 4 (4)(20), and R 1 (2)(7) rings linked into sheets which are parallel to (010).

Related literature

For biological and pharmacological properties of benzo­furan­ones, see: Yogan class="Gene">nathan et al. (2003 ▶); Shode et al. (2002 ▶); Anderson et al. (2005 ▶); Puder et al. (2000 ▶); Nannei et al. (2006 ▶); Brady et al. (2000 ▶); Malpani et al. (2013 ▶). For the synthesis of diverse pyrazole derivatives, see: Abonia et al. (2010 ▶); Insuasty et al. (2012 ▶, 2013 ▶). For hydrogen bonding, see: Nardelli (1995 ▶) and for hydrogen-bond graph-set motifs, see: Etter (1990 ▶); Bernstein et al. (1995 ▶).

Experimental

Crystal data

C18H15N3O2

M = 305.33

Monoclinic,

a = 10.0451 (2) Å

b = 15.0631 (5) Å

c = 12.2008 (4) Å

β = 123.257 (2)°

V = 1543.75 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 295 K

0.32 × 0.22 × 0.15 mm

Data collection

Nonius KappaCCD diffractometer

15125 measured reflections

3449 independent reflections

2264 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.173

S = 1.03

3449 reflections

212 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.29 e Å−3

Δρmin = −0.31 e Å−3

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; 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 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813017479/gg2119sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813017479/gg2119Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813017479/gg2119Isup3.cml

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

C18H15N3O2	F(000) = 640
Mr = 305.33	Dx = 1.314 Mg m−3
Monoclinic, P21/c	Melting point: 464(1) K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 10.0451 (2) Å	Cell parameters from 14996 reflections
b = 15.0631 (5) Å	θ = 2.6–27.5°
c = 12.2008 (4) Å	µ = 0.09 mm−1
β = 123.257 (2)°	T = 295 K
V = 1543.75 (8) Å3	Block, white
Z = 4	0.32 × 0.22 × 0.15 mm

Nonius KappaCCD diffractometer	2264 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.043
Graphite monochromator	θmax = 27.5°, θmin = 3.4°
CCD rotation images, thick slices scans	h = −13→12
15125 measured reflections	k = −19→19
3449 independent reflections	l = −15→12

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.173	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.1038P)2 + 0.1468P] where P = (Fo2 + 2Fc2)/3
3449 reflections	(Δ/σ)max < 0.001
212 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.31 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
O2	−0.07121 (16)	0.81568 (8)	0.27256 (14)	0.0549 (4)
N2	0.36978 (18)	0.72091 (10)	0.28921 (14)	0.0438 (4)
N3	0.27961 (18)	0.77174 (10)	0.17675 (13)	0.0455 (4)
C13	0.4909 (2)	0.66591 (12)	0.29898 (16)	0.0413 (4)
O1	−0.28573 (17)	0.90333 (11)	0.17908 (17)	0.0733 (5)
C11	0.1725 (2)	0.81116 (11)	0.19068 (17)	0.0433 (4)
N1	0.38101 (19)	0.68232 (11)	0.48354 (14)	0.0532 (5)
H1A	0.4582	0.6461	0.5063	0.064*
H1B	0.3447	0.6890	0.5325	0.064*
C7	0.1242 (2)	0.92069 (12)	0.39955 (16)	0.0426 (4)
C10	0.3162 (2)	0.72929 (11)	0.36959 (16)	0.0402 (4)
C14	0.5007 (2)	0.57697 (13)	0.33054 (18)	0.0500 (5)
H14	0.4357	0.5534	0.3556	0.060*
C9	0.1904 (2)	0.78783 (11)	0.31016 (16)	0.0411 (4)
C2	−0.0212 (2)	0.96295 (12)	0.33066 (17)	0.0465 (5)
C6	0.2622 (2)	0.96761 (14)	0.48389 (18)	0.0527 (5)
H6	0.3608	0.9395	0.5306	0.063*
C8	0.1023 (2)	0.82334 (12)	0.36679 (18)	0.0446 (4)
C18	0.5921 (2)	0.70181 (13)	0.26633 (18)	0.0500 (5)
H18	0.5900	0.7624	0.2506	0.060*
C12	0.0453 (2)	0.86596 (14)	0.08062 (18)	0.0559 (5)
H12A	0.0652	0.8701	0.0123	0.084*
H12B	0.0454	0.9244	0.1122	0.084*
H12C	−0.0564	0.8386	0.0467	0.084*
C17	0.6953 (2)	0.64713 (15)	0.2575 (2)	0.0588 (5)
H17	0.7606	0.6705	0.2326	0.071*
C1	−0.1431 (2)	0.89583 (13)	0.2522 (2)	0.0528 (5)
C16	0.7027 (3)	0.55779 (16)	0.2851 (2)	0.0637 (6)
H16	0.7713	0.5210	0.2772	0.076*
C15	0.6087 (3)	0.52322 (14)	0.3245 (2)	0.0603 (5)
H15	0.6175	0.4636	0.3471	0.072*
C3	−0.0347 (3)	1.05330 (14)	0.3422 (2)	0.0609 (6)
H3	−0.1330	1.0816	0.2950	0.073*
C5	0.2482 (3)	1.05762 (15)	0.4961 (2)	0.0646 (6)
H5	0.3388	1.0907	0.5529	0.077*
C4	0.1022 (3)	1.09962 (15)	0.4257 (2)	0.0676 (6)
H4	0.0966	1.1605	0.4351	0.081*
H8	0.130 (2)	0.7852 (12)	0.4451 (19)	0.049 (5)*

	U11	U22	U33	U12	U13	U23
O2	0.0481 (8)	0.0467 (8)	0.0721 (9)	−0.0027 (6)	0.0345 (7)	−0.0020 (6)
N2	0.0513 (9)	0.0464 (8)	0.0380 (7)	0.0083 (7)	0.0272 (7)	0.0052 (6)
N3	0.0530 (10)	0.0484 (9)	0.0372 (8)	0.0065 (7)	0.0262 (7)	0.0059 (6)
C13	0.0418 (10)	0.0467 (10)	0.0363 (8)	0.0021 (8)	0.0219 (8)	−0.0011 (7)
O1	0.0421 (9)	0.0777 (11)	0.0866 (11)	0.0030 (7)	0.0267 (8)	−0.0077 (8)
C11	0.0482 (11)	0.0401 (10)	0.0405 (9)	−0.0007 (8)	0.0237 (8)	0.0005 (7)
N1	0.0624 (11)	0.0635 (10)	0.0424 (9)	0.0210 (8)	0.0344 (8)	0.0143 (7)
C7	0.0471 (11)	0.0470 (10)	0.0400 (9)	0.0025 (8)	0.0280 (8)	0.0023 (7)
C10	0.0456 (10)	0.0407 (10)	0.0363 (9)	−0.0006 (8)	0.0237 (8)	0.0002 (7)
C14	0.0509 (12)	0.0484 (11)	0.0542 (11)	0.0019 (9)	0.0310 (10)	0.0035 (8)
C9	0.0461 (11)	0.0398 (9)	0.0401 (9)	0.0003 (8)	0.0253 (8)	−0.0008 (7)
C2	0.0458 (11)	0.0464 (11)	0.0514 (10)	0.0035 (8)	0.0292 (9)	0.0017 (8)
C6	0.0486 (12)	0.0621 (13)	0.0449 (10)	0.0009 (10)	0.0241 (9)	−0.0054 (9)
C8	0.0450 (11)	0.0462 (10)	0.0458 (10)	0.0033 (8)	0.0270 (9)	0.0059 (8)
C18	0.0513 (12)	0.0520 (11)	0.0476 (10)	−0.0024 (9)	0.0278 (9)	0.0015 (8)
C12	0.0569 (13)	0.0578 (12)	0.0462 (10)	0.0067 (10)	0.0239 (10)	0.0087 (9)
C17	0.0508 (12)	0.0746 (15)	0.0594 (12)	0.0038 (11)	0.0355 (10)	0.0053 (10)
C1	0.0454 (12)	0.0571 (12)	0.0591 (11)	0.0042 (10)	0.0306 (10)	0.0026 (9)
C16	0.0555 (13)	0.0760 (16)	0.0649 (13)	0.0159 (11)	0.0365 (11)	0.0022 (11)
C15	0.0642 (14)	0.0516 (12)	0.0645 (13)	0.0115 (10)	0.0349 (11)	0.0059 (10)
C3	0.0590 (14)	0.0527 (13)	0.0714 (13)	0.0126 (10)	0.0360 (12)	0.0047 (10)
C5	0.0663 (14)	0.0635 (14)	0.0643 (13)	−0.0121 (12)	0.0360 (12)	−0.0164 (11)
C4	0.0804 (17)	0.0472 (12)	0.0795 (15)	0.0007 (12)	0.0465 (14)	−0.0080 (11)

O2—C1	1.358 (2)	C2—C3	1.383 (3)
O2—C8	1.475 (2)	C2—C1	1.467 (3)
N2—C10	1.359 (2)	C6—C5	1.380 (3)
N2—N3	1.388 (2)	C6—H6	0.9300
N2—C13	1.422 (2)	C8—H8	1.013 (19)
N3—C11	1.319 (2)	C18—C17	1.375 (3)
C13—C14	1.382 (3)	C18—H18	0.9300
C13—C18	1.389 (2)	C12—H12A	0.9600
O1—C1	1.208 (2)	C12—H12B	0.9600
C11—C9	1.412 (2)	C12—H12C	0.9600
C11—C12	1.495 (3)	C17—C16	1.379 (3)
N1—C10	1.365 (2)	C17—H17	0.9300
N1—H1A	0.8600	C16—C15	1.375 (3)
N1—H1B	0.8600	C16—H16	0.9300
C7—C2	1.377 (3)	C15—H15	0.9300
C7—C6	1.384 (3)	C3—C4	1.371 (3)
C7—C8	1.504 (3)	C3—H3	0.9300
C10—C9	1.376 (2)	C5—C4	1.381 (3)
C14—C15	1.388 (3)	C5—H5	0.9300
C14—H14	0.9300	C4—H4	0.9300
C9—C8	1.489 (2)
C1—O2—C8	110.83 (14)	C9—C8—C7	115.86 (15)
C10—N2—N3	111.11 (13)	O2—C8—H8	106.9 (11)
C10—N2—C13	130.77 (14)	C9—C8—H8	107.7 (10)
N3—N2—C13	117.96 (13)	C7—C8—H8	112.2 (11)
C11—N3—N2	104.90 (13)	C17—C18—C13	119.47 (18)
C14—C13—C18	120.37 (17)	C17—C18—H18	120.3
C14—C13—N2	121.01 (16)	C13—C18—H18	120.3
C18—C13—N2	118.44 (16)	C11—C12—H12A	109.5
N3—C11—C9	111.71 (16)	C11—C12—H12B	109.5
N3—C11—C12	119.26 (15)	H12A—C12—H12B	109.5
C9—C11—C12	128.82 (17)	C11—C12—H12C	109.5
C10—N1—H1A	120.0	H12A—C12—H12C	109.5
C10—N1—H1B	120.0	H12B—C12—H12C	109.5
H1A—N1—H1B	120.0	C18—C17—C16	120.47 (18)
C2—C7—C6	120.81 (18)	C18—C17—H17	119.8
C2—C7—C8	109.70 (16)	C16—C17—H17	119.8
C6—C7—C8	129.49 (17)	O1—C1—O2	120.95 (19)
N2—C10—N1	122.01 (15)	O1—C1—C2	130.16 (19)
N2—C10—C9	106.96 (14)	O2—C1—C2	108.88 (16)
N1—C10—C9	130.99 (15)	C15—C16—C17	119.97 (19)
C13—C14—C15	119.29 (18)	C15—C16—H16	120.0
C13—C14—H14	120.4	C17—C16—H16	120.0
C15—C14—H14	120.4	C16—C15—C14	120.29 (19)
C10—C9—C11	105.30 (15)	C16—C15—H15	119.9
C10—C9—C8	126.36 (15)	C14—C15—H15	119.9
C11—C9—C8	128.18 (16)	C4—C3—C2	117.51 (19)
C7—C2—C3	121.57 (18)	C4—C3—H3	121.2
C7—C2—C1	107.81 (16)	C2—C3—H3	121.2
C3—C2—C1	130.63 (18)	C6—C5—C4	121.3 (2)
C5—C6—C7	117.50 (19)	C6—C5—H5	119.3
C5—C6—H6	121.2	C4—C5—H5	119.3
C7—C6—H6	121.2	C3—C4—C5	121.3 (2)
O2—C8—C9	111.06 (14)	C3—C4—H4	119.4
O2—C8—C7	102.78 (14)	C5—C4—H4	119.4
C10—N2—N3—C11	0.49 (19)	C1—O2—C8—C9	−124.84 (16)
C13—N2—N3—C11	176.40 (15)	C1—O2—C8—C7	−0.32 (18)
C10—N2—C13—C14	45.9 (3)	C10—C9—C8—O2	−131.54 (18)
N3—N2—C13—C14	−129.02 (17)	C11—C9—C8—O2	53.7 (2)
C10—N2—C13—C18	−138.91 (19)	C10—C9—C8—C7	111.7 (2)
N3—N2—C13—C18	46.1 (2)	C11—C9—C8—C7	−63.1 (2)
N2—N3—C11—C9	0.29 (19)	C2—C7—C8—O2	−0.28 (17)
N2—N3—C11—C12	−174.89 (15)	C6—C7—C8—O2	179.67 (16)
N3—N2—C10—N1	176.82 (16)	C2—C7—C8—C9	121.01 (17)
C13—N2—C10—N1	1.6 (3)	C6—C7—C8—C9	−59.0 (2)
N3—N2—C10—C9	−1.07 (19)	C14—C13—C18—C17	4.1 (3)
C13—N2—C10—C9	−176.30 (17)	N2—C13—C18—C17	−171.06 (16)
C18—C13—C14—C15	−2.4 (3)	C13—C18—C17—C16	−2.3 (3)
N2—C13—C14—C15	172.66 (17)	C8—O2—C1—O1	−179.17 (17)
N2—C10—C9—C11	1.17 (19)	C8—O2—C1—C2	0.8 (2)
N1—C10—C9—C11	−176.46 (18)	C7—C2—C1—O1	179.0 (2)
N2—C10—C9—C8	−174.57 (16)	C3—C2—C1—O1	−0.7 (4)
N1—C10—C9—C8	7.8 (3)	C7—C2—C1—O2	−0.9 (2)
N3—C11—C9—C10	−0.9 (2)	C3—C2—C1—O2	179.40 (18)
C12—C11—C9—C10	173.66 (17)	C18—C17—C16—C15	−1.3 (3)
N3—C11—C9—C8	174.71 (17)	C17—C16—C15—C14	3.1 (3)
C12—C11—C9—C8	−10.7 (3)	C13—C14—C15—C16	−1.2 (3)
C6—C7—C2—C3	0.5 (3)	C7—C2—C3—C4	−0.4 (3)
C8—C7—C2—C3	−179.57 (16)	C1—C2—C3—C4	179.19 (19)
C6—C7—C2—C1	−179.22 (16)	C7—C6—C5—C4	−0.8 (3)
C8—C7—C2—C1	0.73 (19)	C2—C3—C4—C5	−0.2 (3)
C2—C7—C6—C5	0.1 (3)	C6—C5—C4—C3	0.8 (3)
C8—C7—C6—C5	−179.82 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1i	0.86	2.38	3.131 (2)	146
N1—H1B···N3ii	0.86	2.27	3.116 (2)	169
C8—H8···N3ii	1.013 (19)	2.51 (2)	3.484 (2)	159.9 (15)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.86	2.38	3.131 (2)	146
N1—H1B⋯N3ii	0.86	2.27	3.116 (2)	169
C8—H8⋯N3ii	1.013 (19)	2.51 (2)	3.484 (2)	159.9 (15)

Symmetry codes: (i) ; (ii) .