3,4-Dimethyl-1-phenyl-pyrano[2,3-c]pyrazol-6(1H)-one.

In the title compound, C(14)H(12)N(2)O(2), the dihedral angle between the phenyl ring and the 3,4-dimethyl-pyrano[2,3-c]pyrazol-6(1H)-one system is 7.28 (6)°. An intra-molecular C-H⋯O inter-action generates an S(6) ring. In the crystal, the mol-ecules are linked by C-H⋯O hydrogen bonds, forming C(8) chains. C-H⋯π and π-π inter-actions [centroid-centroid separation = 3.6374 (12) Å] further consolidate the packing.

Related literature

For a related structure, see: Ramsay & Steel (1985) ▶. For background to the pyrano[2,3-c]pyrazol-6-one ring system, see: Abdallah & Zaki (1999 ▶); Huang et al. (1992 ▶); Khan et al. (1982 ▶); Kuo et al. (1984 ▶); Ramsay & Steel (1985) ▶; Samaritoni et al. (2007 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C14H12N2O2

M = 240.26

Monoclinic,

a = 15.1231 (9) Å

b = 13.3558 (8) Å

c = 13.8684 (8) Å

β = 120.965 (2)°

V = 2401.9 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.35 × 0.25 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.975, T max = 0.982

9214 measured reflections

2171 independent reflections

1382 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.140

S = 1.02

2171 reflections

165 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.19 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, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811011317/hb5827sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811011317/hb5827Isup2.hkl

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

C14H12N2O2	F(000) = 1008
Mr = 240.26	Dx = 1.329 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1382 reflections
a = 15.1231 (9) Å	θ = 2.2–25.3°
b = 13.3558 (8) Å	µ = 0.09 mm−1
c = 13.8684 (8) Å	T = 296 K
β = 120.965 (2)°	Rod, light brown
V = 2401.9 (3) Å3	0.35 × 0.25 × 0.25 mm
Z = 8

Bruker Kappa APEXII CCD diffractometer	2171 independent reflections
Radiation source: fine-focus sealed tube	1382 reflections with I > 2σ(I)
graphite	Rint = 0.032
Detector resolution: 8.10 pixels mm-1	θmax = 25.3°, θmin = 2.2°
ω scans	h = −18→14
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −15→16
Tmin = 0.975, Tmax = 0.982	l = −9→16
9214 measured reflections

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) = 0.140	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0723P)2 + 0.5405P] where P = (Fo2 + 2Fc2)/3
2171 reflections	(Δ/σ)max < 0.001
165 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
O1	0.01582 (9)	0.63464 (9)	0.13521 (10)	0.0584 (5)
O2	−0.07464 (12)	0.77525 (12)	0.09062 (16)	0.0994 (7)
N1	0.09619 (12)	0.47598 (11)	0.16813 (13)	0.0526 (6)
N2	0.06513 (14)	0.37672 (12)	0.14972 (16)	0.0689 (7)
C1	0.20381 (14)	0.49922 (15)	0.22105 (15)	0.0526 (7)
C2	0.27219 (16)	0.42241 (17)	0.24254 (18)	0.0661 (8)
C3	0.37688 (16)	0.44318 (19)	0.2968 (2)	0.0794 (9)
C4	0.41168 (17)	0.5391 (2)	0.3279 (2)	0.0825 (9)
C5	0.34341 (16)	0.61512 (19)	0.30539 (19)	0.0770 (9)
C6	0.23861 (15)	0.59574 (16)	0.25142 (17)	0.0613 (8)
C7	0.01255 (14)	0.53448 (14)	0.13093 (15)	0.0484 (7)
C8	−0.08080 (15)	0.68528 (17)	0.08827 (18)	0.0659 (8)
C9	−0.17132 (15)	0.62522 (17)	0.04570 (17)	0.0638 (8)
C10	−0.17218 (14)	0.52456 (16)	0.04351 (15)	0.0537 (7)
C11	−0.07438 (14)	0.47628 (14)	0.08801 (16)	0.0519 (7)
C12	−0.03607 (17)	0.37748 (16)	0.10228 (19)	0.0657 (8)
C13	−0.0944 (2)	0.28099 (17)	0.0706 (3)	0.1025 (13)
C14	−0.27056 (15)	0.46714 (18)	−0.00325 (19)	0.0709 (8)
H2	0.24847	0.35727	0.22090	0.0793*
H3	0.42364	0.39162	0.31212	0.0953*
H4	0.48198	0.55248	0.36445	0.0990*
H5	0.36739	0.68028	0.32639	0.0924*
H6	0.19215	0.64766	0.23586	0.0736*
H9	−0.23416	0.65797	0.01749	0.0766*
H13A	−0.04834	0.22680	0.08183	0.1536*
H13B	−0.14832	0.28336	−0.00699	0.1536*
H13C	−0.12397	0.27081	0.11674	0.1536*
H14A	−0.32644	0.51265	−0.02276	0.1064*
H14B	−0.26542	0.42052	0.05210	0.1064*
H14C	−0.28305	0.43135	−0.06914	0.1064*

	U11	U22	U33	U12	U13	U23
O1	0.0380 (8)	0.0474 (9)	0.0769 (9)	0.0008 (6)	0.0203 (7)	−0.0016 (6)
O2	0.0515 (10)	0.0514 (11)	0.1565 (16)	0.0033 (8)	0.0259 (10)	−0.0053 (10)
N1	0.0409 (9)	0.0431 (10)	0.0687 (10)	0.0025 (8)	0.0245 (8)	0.0023 (7)
N2	0.0509 (12)	0.0454 (11)	0.1012 (13)	−0.0024 (8)	0.0325 (10)	0.0020 (9)
C1	0.0375 (11)	0.0555 (13)	0.0584 (11)	0.0036 (9)	0.0201 (9)	0.0015 (9)
C2	0.0503 (13)	0.0581 (14)	0.0807 (14)	0.0098 (11)	0.0272 (11)	0.0040 (10)
C3	0.0478 (14)	0.0753 (17)	0.1009 (17)	0.0200 (13)	0.0282 (13)	0.0069 (13)
C4	0.0374 (12)	0.0844 (18)	0.1021 (18)	0.0021 (13)	0.0191 (12)	−0.0092 (14)
C5	0.0428 (13)	0.0728 (16)	0.0992 (17)	−0.0039 (12)	0.0249 (12)	−0.0147 (13)
C6	0.0401 (12)	0.0550 (14)	0.0797 (13)	0.0014 (10)	0.0243 (10)	−0.0064 (10)
C7	0.0422 (11)	0.0434 (12)	0.0572 (11)	0.0013 (9)	0.0238 (9)	0.0009 (9)
C8	0.0431 (12)	0.0519 (14)	0.0856 (14)	0.0050 (11)	0.0208 (11)	−0.0010 (11)
C9	0.0357 (11)	0.0631 (15)	0.0793 (14)	0.0022 (10)	0.0201 (10)	−0.0039 (11)
C10	0.0411 (11)	0.0572 (13)	0.0587 (11)	−0.0032 (9)	0.0228 (9)	−0.0021 (9)
C11	0.0410 (11)	0.0496 (12)	0.0620 (12)	−0.0029 (9)	0.0244 (9)	−0.0002 (9)
C12	0.0525 (13)	0.0489 (14)	0.0905 (15)	−0.0057 (10)	0.0331 (12)	0.0013 (10)
C13	0.0688 (17)	0.0521 (16)	0.166 (3)	−0.0132 (13)	0.0457 (17)	−0.0009 (15)
C14	0.0444 (12)	0.0789 (16)	0.0838 (14)	−0.0161 (11)	0.0289 (11)	−0.0101 (12)

O1—C7	1.339 (2)	C10—C11	1.430 (3)
O1—C8	1.427 (3)	C10—C14	1.493 (3)
O2—C8	1.204 (3)	C11—C12	1.414 (3)
N1—N2	1.386 (2)	C12—C13	1.494 (4)
N1—C1	1.433 (3)	C2—H2	0.9300
N1—C7	1.344 (3)	C3—H3	0.9300
N2—C12	1.319 (4)	C4—H4	0.9300
C1—C2	1.376 (3)	C5—H5	0.9300
C1—C6	1.374 (3)	C6—H6	0.9300
C2—C3	1.387 (4)	C9—H9	0.9300
C3—C4	1.368 (4)	C13—H13A	0.9600
C4—C5	1.365 (4)	C13—H13B	0.9600
C5—C6	1.385 (4)	C13—H13C	0.9600
C7—C11	1.372 (3)	C14—H14A	0.9600
C8—C9	1.426 (3)	C14—H14B	0.9600
C9—C10	1.345 (3)	C14—H14C	0.9600
C7—O1—C8	116.58 (17)	N2—C12—C13	119.9 (2)
N2—N1—C1	119.31 (17)	C11—C12—C13	128.8 (3)
N2—N1—C7	108.83 (18)	C1—C2—H2	120.00
C1—N1—C7	131.86 (16)	C3—C2—H2	120.00
N1—N2—C12	106.32 (18)	C2—C3—H3	120.00
N1—C1—C2	118.57 (18)	C4—C3—H3	120.00
N1—C1—C6	121.0 (2)	C3—C4—H4	120.00
C2—C1—C6	120.4 (2)	C5—C4—H4	120.00
C1—C2—C3	119.3 (2)	C4—C5—H5	120.00
C2—C3—C4	120.3 (2)	C6—C5—H5	120.00
C3—C4—C5	120.1 (3)	C1—C6—H6	120.00
C4—C5—C6	120.4 (2)	C5—C6—H6	120.00
C1—C6—C5	119.5 (2)	C8—C9—H9	118.00
O1—C7—N1	123.92 (19)	C10—C9—H9	118.00
O1—C7—C11	126.2 (2)	C12—C13—H13A	109.00
N1—C7—C11	109.87 (17)	C12—C13—H13B	109.00
O1—C8—O2	114.4 (2)	C12—C13—H13C	109.00
O1—C8—C9	117.49 (19)	H13A—C13—H13B	109.00
O2—C8—C9	128.1 (2)	H13A—C13—H13C	109.00
C8—C9—C10	124.6 (2)	H13B—C13—H13C	109.00
C9—C10—C11	116.4 (2)	C10—C14—H14A	109.00
C9—C10—C14	121.3 (2)	C10—C14—H14B	109.00
C11—C10—C14	122.28 (19)	C10—C14—H14C	109.00
C7—C11—C10	118.64 (18)	H14A—C14—H14B	109.00
C7—C11—C12	103.7 (2)	H14A—C14—H14C	109.00
C10—C11—C12	137.7 (2)	H14B—C14—H14C	109.00
N2—C12—C11	111.3 (2)
C8—O1—C7—N1	177.83 (18)	C1—C2—C3—C4	−0.5 (4)
C8—O1—C7—C11	−1.5 (3)	C2—C3—C4—C5	−0.2 (4)
C7—O1—C8—O2	−177.76 (19)	C3—C4—C5—C6	0.3 (4)
C7—O1—C8—C9	2.7 (3)	C4—C5—C6—C1	0.3 (3)
C1—N1—N2—C12	179.03 (18)	O1—C7—C11—C10	−0.4 (3)
C7—N1—N2—C12	−0.1 (2)	O1—C7—C11—C12	179.28 (19)
N2—N1—C1—C2	5.9 (3)	N1—C7—C11—C10	−179.82 (17)
N2—N1—C1—C6	−173.10 (19)	N1—C7—C11—C12	−0.1 (2)
C7—N1—C1—C2	−175.1 (2)	O1—C8—C9—C10	−2.2 (3)
C7—N1—C1—C6	5.8 (3)	O2—C8—C9—C10	178.3 (2)
N2—N1—C7—O1	−179.24 (17)	C8—C9—C10—C11	0.3 (3)
N2—N1—C7—C11	0.2 (2)	C8—C9—C10—C14	−179.6 (2)
C1—N1—C7—O1	1.7 (3)	C9—C10—C11—C7	1.0 (3)
C1—N1—C7—C11	−178.87 (19)	C9—C10—C11—C12	−178.6 (2)
N1—N2—C12—C11	0.1 (2)	C14—C10—C11—C7	−179.04 (19)
N1—N2—C12—C13	179.6 (2)	C14—C10—C11—C12	1.4 (4)
N1—C1—C2—C3	−178.0 (2)	C7—C11—C12—N2	0.0 (3)
C6—C1—C2—C3	1.0 (3)	C7—C11—C12—C13	−179.5 (3)
N1—C1—C6—C5	178.11 (19)	C10—C11—C12—N2	179.6 (2)
C2—C1—C6—C5	−0.9 (3)	C10—C11—C12—C13	0.1 (5)

Cg3 is the centroid of the C1–C6 phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O2i	0.93	2.51	3.407 (3)	163
C6—H6···O1	0.93	2.29	2.938 (3)	126
C14—H14C···Cg3ii	0.96	2.75	3.506 (2)	136

Table 1

Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C1–C6 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O2i	0.93	2.51	3.407 (3)	163
C6—H6⋯O1	0.93	2.29	2.938 (3)	126
C14—H14C⋯Cg3ii	0.96	2.75	3.506 (2)	136

Symmetry codes: (i) ; (ii) .