6-(4-Chloro-phen-yl)-2-(4-meth-oxy-phen-yl)-6,7-dihydro-4H-pyrazolo-[5,1-c][1,4]oxazine.

In the title compound, C(19)H(17)ClN(2)O(2), the pyrazole ring is almost planar with a maximum deviation of 0.009 (3) Å and makes a dihedral angle of 8.96 (9)° with the oxazine ring. The dihedral angles between the pyrazole ring and the chlorine- and meth-oxy-substituted benzene rings are 50.95 (8) and 13.24 (9)°, respectively. An inter-molecular C-H⋯N hydrogen bond links the mol-ecules into infinite chains along the a axis. The crystal structure is further stabilized by C-H⋯π inter-actions.

Related literature

For the pharmacological activity of pyrazole fused-heterocycles, see: Liu et al. (2011 ▶); Kumar et al. (2011 ▶); Guerrini et al. (2010 ▶). For related structures, see: Wei et al. (2007 ▶); Xie et al. (2009 ▶); Shimizu et al. (1990 ▶).

Experimental

Crystal data

C19H17ClN2O2

M = 340.80

Monoclinic,

a = 6.0800 (8) Å

b = 34.224 (5) Å

c = 8.1217 (11) Å

β = 91.186 (3)°

V = 1689.6 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.24 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, 2007 ▶) T min = 0.965, T max = 0.977

8891 measured reflections

2995 independent reflections

1620 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.123

S = 1.02

2995 reflections

218 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: APEX2 (Bruker, 2007 ▶); 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 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811025906/ng5186sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811025906/ng5186Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811025906/ng5186Isup3.cml

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

C19H17ClN2O2	F(000) = 712
Mr = 340.80	Dx = 1.340 Mg m−3Dm = 1.340 Mg m−3Dm measured by not measured
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1213 reflections
a = 6.0800 (8) Å	θ = 3.4–19.3°
b = 34.224 (5) Å	µ = 0.24 mm−1
c = 8.1217 (11) Å	T = 298 K
β = 91.186 (3)°	Block, colourless
V = 1689.6 (4) Å3	0.15 × 0.12 × 0.10 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	2995 independent reflections
Radiation source: fine-focus sealed tube	1620 reflections with I > 2σ(I)
graphite	Rint = 0.043
φ and ω scans	θmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −7→7
Tmin = 0.965, Tmax = 0.977	k = −40→37
8891 measured reflections	l = −6→9

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0496P)2 + 0.0204P] where P = (Fo2 + 2Fc2)/3
2995 reflections	(Δ/σ)max < 0.001
218 parameters	Δρmax = 0.16 e Å−3
1 restraint	Δρmin = −0.24 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	0.30584 (16)	0.48228 (2)	0.68319 (12)	0.1196 (4)
O1	0.9536 (3)	0.04587 (5)	0.5717 (3)	0.0913 (6)
O2	0.1081 (3)	0.29880 (5)	0.4635 (2)	0.0731 (5)
N1	0.6176 (3)	0.22476 (6)	0.5415 (3)	0.0634 (6)
N2	0.4637 (3)	0.25198 (6)	0.4972 (2)	0.0616 (6)
C1	1.1487 (5)	0.04055 (9)	0.6669 (4)	0.1062 (11)
H1A	1.2629	0.0568	0.6243	0.159*
H1B	1.1932	0.0137	0.6617	0.159*
H1C	1.1224	0.0475	0.7792	0.159*
C2	0.8607 (4)	0.08212 (8)	0.5635 (3)	0.0664 (7)
C3	0.9452 (4)	0.11536 (8)	0.6365 (3)	0.0694 (8)
H3	1.0751	0.1142	0.6988	0.083*
C4	0.8355 (4)	0.15036 (8)	0.6166 (3)	0.0683 (7)
H4	0.8946	0.1727	0.6652	0.082*
C5	0.6404 (4)	0.15335 (7)	0.5267 (3)	0.0588 (7)
C6	0.5596 (5)	0.11944 (8)	0.4548 (4)	0.0826 (9)
H6	0.4298	0.1204	0.3924	0.099*
C7	0.6668 (5)	0.08457 (8)	0.4738 (4)	0.0857 (9)
H7	0.6078	0.0622	0.4254	0.103*
C8	0.5221 (4)	0.19052 (7)	0.5029 (3)	0.0576 (6)
C9	0.3076 (4)	0.19647 (8)	0.4394 (3)	0.0644 (7)
H9	0.2073	0.1774	0.4060	0.077*
C10	0.2768 (4)	0.23584 (8)	0.4367 (3)	0.0610 (7)
C11	0.0911 (4)	0.26170 (8)	0.3834 (4)	0.0729 (8)
H11A	0.0938	0.2653	0.2650	0.087*
H11B	−0.0476	0.2495	0.4104	0.087*
C12	0.3161 (4)	0.31656 (7)	0.4375 (3)	0.0659 (7)
H12	0.3449	0.3167	0.3192	0.079*
C13	0.4982 (4)	0.29340 (7)	0.5270 (3)	0.0661 (7)
H13A	0.6408	0.3012	0.4868	0.079*
H13B	0.4951	0.2987	0.6442	0.079*
C14	0.3092 (4)	0.35817 (8)	0.4984 (3)	0.0626 (7)
C15	0.4814 (5)	0.38322 (8)	0.4675 (3)	0.0739 (8)
H15	0.6001	0.3741	0.4082	0.089*
C16	0.4825 (5)	0.42145 (8)	0.5224 (4)	0.0818 (9)
H16	0.6003	0.4378	0.5005	0.098*
C17	0.3068 (5)	0.43484 (8)	0.6096 (4)	0.0790 (8)
C18	0.1343 (5)	0.41086 (9)	0.6415 (3)	0.0797 (8)
H18	0.0157	0.4203	0.7001	0.096*
C19	0.1340 (4)	0.37241 (8)	0.5870 (3)	0.0720 (8)
H19	0.0160	0.3562	0.6100	0.086*

	U11	U22	U33	U12	U13	U23
Cl1	0.1541 (9)	0.0772 (6)	0.1269 (8)	0.0344 (6)	−0.0109 (7)	−0.0143 (5)
O1	0.0986 (15)	0.0626 (13)	0.1113 (17)	0.0022 (11)	−0.0298 (13)	−0.0065 (11)
O2	0.0562 (11)	0.0821 (13)	0.0810 (14)	0.0034 (9)	0.0026 (9)	−0.0061 (10)
N1	0.0566 (12)	0.0586 (14)	0.0750 (15)	0.0020 (11)	0.0004 (11)	−0.0024 (11)
N2	0.0523 (12)	0.0614 (14)	0.0712 (15)	−0.0045 (11)	0.0034 (11)	−0.0028 (11)
C1	0.091 (2)	0.082 (2)	0.144 (3)	0.0093 (18)	−0.020 (2)	0.003 (2)
C2	0.0752 (19)	0.0569 (18)	0.0669 (19)	−0.0041 (14)	−0.0046 (15)	0.0004 (14)
C3	0.0641 (17)	0.0671 (19)	0.077 (2)	−0.0056 (14)	−0.0116 (14)	−0.0058 (15)
C4	0.0655 (17)	0.0610 (18)	0.078 (2)	−0.0139 (14)	−0.0026 (15)	−0.0078 (14)
C5	0.0616 (16)	0.0598 (17)	0.0548 (17)	−0.0096 (13)	0.0021 (13)	−0.0013 (13)
C6	0.083 (2)	0.070 (2)	0.094 (2)	−0.0036 (17)	−0.0283 (17)	−0.0106 (17)
C7	0.091 (2)	0.065 (2)	0.099 (2)	−0.0084 (16)	−0.0333 (19)	−0.0116 (16)
C8	0.0619 (17)	0.0588 (17)	0.0522 (16)	−0.0094 (13)	0.0047 (13)	−0.0021 (12)
C9	0.0611 (17)	0.074 (2)	0.0584 (18)	−0.0141 (14)	0.0027 (14)	−0.0028 (13)
C10	0.0566 (16)	0.0723 (19)	0.0544 (17)	−0.0065 (14)	0.0063 (13)	−0.0046 (13)
C11	0.0615 (16)	0.081 (2)	0.076 (2)	−0.0010 (15)	−0.0031 (14)	−0.0012 (16)
C12	0.0608 (16)	0.0746 (19)	0.0626 (18)	0.0013 (14)	0.0091 (14)	0.0027 (14)
C13	0.0558 (16)	0.0622 (17)	0.081 (2)	0.0028 (13)	0.0080 (14)	−0.0054 (14)
C14	0.0635 (16)	0.0686 (18)	0.0558 (17)	0.0132 (15)	0.0004 (13)	0.0026 (13)
C15	0.0754 (19)	0.072 (2)	0.075 (2)	0.0103 (16)	0.0104 (15)	0.0025 (15)
C16	0.085 (2)	0.067 (2)	0.094 (2)	0.0066 (16)	0.0010 (18)	0.0078 (16)
C17	0.091 (2)	0.074 (2)	0.071 (2)	0.0246 (14)	−0.0134 (17)	0.0015 (15)
C18	0.0781 (19)	0.085 (2)	0.075 (2)	0.0335 (13)	0.0018 (16)	−0.0026 (16)
C19	0.0664 (17)	0.083 (2)	0.0668 (19)	0.0155 (15)	0.0013 (15)	0.0057 (15)

Cl1—C17	1.730 (3)	C7—H7	0.9300
O1—C2	1.364 (3)	C8—C9	1.408 (3)
O1—C1	1.414 (3)	C9—C10	1.361 (3)
O2—C12	1.423 (3)	C9—H9	0.9300
O2—C11	1.429 (3)	C10—C11	1.491 (3)
N1—C8	1.342 (3)	C11—H11A	0.9700
N1—N2	1.363 (2)	C11—H11B	0.9700
N2—C10	1.347 (3)	C12—C14	1.508 (3)
N2—C13	1.452 (3)	C12—C13	1.533 (3)
C1—H1A	0.9600	C12—H12	0.9800
C1—H1B	0.9600	C13—H13A	0.9700
C1—H1C	0.9600	C13—H13B	0.9700
C2—C7	1.375 (3)	C14—C15	1.380 (3)
C2—C3	1.378 (3)	C14—C19	1.386 (3)
C3—C4	1.379 (3)	C15—C16	1.382 (3)
C3—H3	0.9300	C15—H15	0.9300
C4—C5	1.384 (3)	C16—C17	1.373 (4)
C4—H4	0.9300	C16—H16	0.9300
C5—C6	1.384 (3)	C17—C18	1.361 (4)
C5—C8	1.472 (3)	C18—C19	1.388 (4)
C6—C7	1.367 (3)	C18—H18	0.9300
C6—H6	0.9300	C19—H19	0.9300
C2—O1—C1	119.1 (2)	C9—C10—C11	134.1 (2)
C12—O2—C11	111.61 (19)	O2—C11—C10	110.4 (2)
C8—N1—N2	104.12 (19)	O2—C11—H11A	109.6
C10—N2—N1	112.7 (2)	C10—C11—H11A	109.6
C10—N2—C13	125.4 (2)	O2—C11—H11B	109.6
N1—N2—C13	121.79 (19)	C10—C11—H11B	109.6
O1—C1—H1A	109.5	H11A—C11—H11B	108.1
O1—C1—H1B	109.5	O2—C12—C14	108.9 (2)
H1A—C1—H1B	109.5	O2—C12—C13	110.1 (2)
O1—C1—H1C	109.5	C14—C12—C13	111.0 (2)
H1A—C1—H1C	109.5	O2—C12—H12	108.9
H1B—C1—H1C	109.5	C14—C12—H12	108.9
O1—C2—C7	115.5 (2)	C13—C12—H12	108.9
O1—C2—C3	125.4 (3)	N2—C13—C12	109.0 (2)
C7—C2—C3	119.1 (3)	N2—C13—H13A	109.9
C2—C3—C4	119.4 (2)	C12—C13—H13A	109.9
C2—C3—H3	120.3	N2—C13—H13B	109.9
C4—C3—H3	120.3	C12—C13—H13B	109.9
C3—C4—C5	122.2 (2)	H13A—C13—H13B	108.3
C3—C4—H4	118.9	C15—C14—C19	118.0 (3)
C5—C4—H4	118.9	C15—C14—C12	120.1 (2)
C4—C5—C6	117.0 (2)	C19—C14—C12	121.9 (3)
C4—C5—C8	123.0 (2)	C14—C15—C16	121.9 (3)
C6—C5—C8	120.1 (2)	C14—C15—H15	119.1
C7—C6—C5	121.3 (3)	C16—C15—H15	119.1
C7—C6—H6	119.3	C17—C16—C15	118.9 (3)
C5—C6—H6	119.3	C17—C16—H16	120.5
C6—C7—C2	121.0 (3)	C15—C16—H16	120.5
C6—C7—H7	119.5	C18—C17—C16	120.5 (3)
C2—C7—H7	119.5	C18—C17—Cl1	119.5 (2)
N1—C8—C9	110.6 (2)	C16—C17—Cl1	120.0 (3)
N1—C8—C5	121.1 (2)	C17—C18—C19	120.5 (3)
C9—C8—C5	128.3 (2)	C17—C18—H18	119.8
C10—C9—C8	106.0 (2)	C19—C18—H18	119.8
C10—C9—H9	127.0	C14—C19—C18	120.2 (3)
C8—C9—H9	127.0	C14—C19—H19	119.9
N2—C10—C9	106.6 (2)	C18—C19—H19	119.9
N2—C10—C11	119.4 (2)
C8—N1—N2—C10	1.4 (3)	C8—C9—C10—N2	−0.5 (3)
C8—N1—N2—C13	176.7 (2)	C8—C9—C10—C11	179.3 (3)
C1—O1—C2—C7	−177.6 (3)	C12—O2—C11—C10	54.9 (3)
C1—O1—C2—C3	2.4 (4)	N2—C10—C11—O2	−22.8 (3)
O1—C2—C3—C4	179.2 (2)	C9—C10—C11—O2	157.4 (3)
C7—C2—C3—C4	−0.8 (4)	C11—O2—C12—C14	170.0 (2)
C2—C3—C4—C5	0.8 (4)	C11—O2—C12—C13	−68.1 (3)
C3—C4—C5—C6	−0.7 (4)	C10—N2—C13—C12	−15.0 (3)
C3—C4—C5—C8	−179.5 (2)	N1—N2—C13—C12	170.3 (2)
C4—C5—C6—C7	0.8 (4)	O2—C12—C13—N2	44.8 (3)
C8—C5—C6—C7	179.5 (3)	C14—C12—C13—N2	165.4 (2)
C5—C6—C7—C2	−0.8 (5)	O2—C12—C14—C15	−171.6 (2)
O1—C2—C7—C6	−179.1 (3)	C13—C12—C14—C15	67.1 (3)
C3—C2—C7—C6	0.8 (5)	O2—C12—C14—C19	9.0 (3)
N2—N1—C8—C9	−1.7 (3)	C13—C12—C14—C19	−112.4 (3)
N2—N1—C8—C5	177.7 (2)	C19—C14—C15—C16	0.0 (4)
C4—C5—C8—N1	12.5 (4)	C12—C14—C15—C16	−179.4 (2)
C6—C5—C8—N1	−166.2 (2)	C14—C15—C16—C17	−0.2 (4)
C4—C5—C8—C9	−168.2 (2)	C15—C16—C17—C18	0.0 (4)
C6—C5—C8—C9	13.1 (4)	C15—C16—C17—Cl1	178.8 (2)
N1—C8—C9—C10	1.4 (3)	C16—C17—C18—C19	0.4 (4)
C5—C8—C9—C10	−177.9 (2)	Cl1—C17—C18—C19	−178.45 (19)
N1—N2—C10—C9	−0.6 (3)	C15—C14—C19—C18	0.3 (4)
C13—N2—C10—C9	−175.6 (2)	C12—C14—C19—C18	179.7 (2)
N1—N2—C10—C11	179.6 (2)	C17—C18—C19—C14	−0.5 (4)
C13—N2—C10—C11	4.5 (4)

Cg1 and Cg2 are the centroids of the N1,N2,C8–C10 and C14–C19 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11B···N1i	0.97	2.47	3.419 (3)	167
C13—H13B···Cg1ii	0.97	2.86	3.762 (3)	156
C6—H6···Cg2iii	0.93	2.89	3.608 (3)	135

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the N1,N2,C8–C10 and C14–C19 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11B⋯N1i	0.97	2.47	3.419 (3)	167
C13—H13B⋯Cg1ii	0.97	2.86	3.762 (3)	156
C6—H6⋯Cg2iii	0.93	2.89	3.608 (3)	135

Symmetry codes: (i) ; (ii) ; (iii) .