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

The title compound, C(14)H(12)N(2)O(2), is almost planar with an r.m.s. deviation for all non-H atoms of 0.038 Å. The observed planarity is rationalized in terms of a close intra-molecular C-H⋯O inter-action. Supra-molecular layers, two mol-ecules thick and with a step topology, are formed in the crystal packing via C-H⋯O contacts involving the carbonyl O atom, which accepts two such bonds, and π-π inter-actions between the components of the fused ring system and the phenyl ring of inversion-related mol-ecules [centroid-centroid distances = 3.6819 (13) and 3.6759 (12) Å].

Related literature

For the analgesic and anti-inflammatory activities of pyrano[2,3-c]pyrazole derivatives, see: Kuo et al. (1984 ▶). For the synthesis, see: Gelin et al. (1983 ▶).

Experimental

Crystal data

C14H12N2O2

M = 240.26

Triclinic,

a = 6.7200 (6) Å

b = 8.2201 (8) Å

c = 11.2616 (7) Å

α = 93.914 (6)°

β = 95.162 (6)°

γ = 108.721 (8)°

V = 583.66 (9) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.40 × 0.30 × 0.20 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.964, T max = 0.982

4356 measured reflections

2676 independent reflections

1946 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.158

S = 1.05

2676 reflections

165 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.38 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812011348/su2391sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812011348/su2391Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812011348/su2391Isup3.cml

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

C14H12N2O2	Z = 2
Mr = 240.26	F(000) = 252
Triclinic, P1	Dx = 1.367 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.7200 (6) Å	Cell parameters from 1310 reflections
b = 8.2201 (8) Å	θ = 2.6–27.5°
c = 11.2616 (7) Å	µ = 0.09 mm−1
α = 93.914 (6)°	T = 100 K
β = 95.162 (6)°	Prism, orange
γ = 108.721 (8)°	0.40 × 0.30 × 0.20 mm
V = 583.66 (9) Å3

Agilent SuperNova Dual diffractometer with an Atlas detector	2676 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	1946 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.031
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 2.6°
ω scan	h = −8→8
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −10→9
Tmin = 0.964, Tmax = 0.982	l = −14→14
4356 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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.158	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0761P)2 + 0.084P] where P = (Fo2 + 2Fc2)/3
2676 reflections	(Δ/σ)max = 0.001
165 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.38 e Å−3

	x	y	z	Uiso*/Ueq
O1	0.6182 (2)	0.25349 (16)	0.35598 (11)	0.0238 (3)
O2	0.6446 (2)	0.28672 (19)	−0.00902 (12)	0.0349 (4)
N1	0.7795 (2)	0.55863 (19)	0.37569 (13)	0.0216 (4)
N2	0.8481 (3)	0.6876 (2)	0.30000 (14)	0.0257 (4)
C1	0.4637 (3)	−0.0519 (3)	0.33142 (18)	0.0336 (5)
H1A	0.4058	−0.1514	0.2706	0.050*
H1B	0.3523	−0.0428	0.3793	0.050*
H1C	0.5797	−0.0671	0.3838	0.050*
C2	0.5447 (3)	0.1084 (2)	0.27152 (17)	0.0266 (4)
C3	0.5520 (3)	0.1187 (3)	0.15402 (17)	0.0284 (5)
H3	0.4976	0.0145	0.1020	0.034*
C4	0.6380 (3)	0.2797 (3)	0.10026 (17)	0.0276 (5)
C5	0.7110 (3)	0.4278 (2)	0.18953 (16)	0.0245 (4)
C6	0.6979 (3)	0.4044 (2)	0.30916 (16)	0.0221 (4)
C7	0.8072 (3)	0.6086 (3)	0.18951 (17)	0.0266 (4)
C8	0.8643 (4)	0.7086 (3)	0.08486 (18)	0.0339 (5)
H8A	0.9106	0.8324	0.1112	0.051*
H8B	0.7406	0.6789	0.0243	0.051*
H8C	0.9792	0.6801	0.0502	0.051*
C9	0.8063 (3)	0.6061 (2)	0.50196 (16)	0.0221 (4)
C10	0.7333 (3)	0.4863 (2)	0.58291 (17)	0.0262 (4)
H10	0.6643	0.3678	0.5554	0.031*
C11	0.7627 (3)	0.5423 (3)	0.70503 (17)	0.0261 (4)
H11	0.7132	0.4613	0.7609	0.031*
C12	0.8638 (3)	0.7155 (3)	0.74549 (17)	0.0262 (4)
H12	0.8826	0.7529	0.8287	0.031*
C13	0.9367 (3)	0.8327 (3)	0.66445 (17)	0.0269 (4)
H13	1.0062	0.9511	0.6922	0.032*
C14	0.9096 (3)	0.7798 (2)	0.54306 (17)	0.0259 (4)
H14	0.9611	0.8613	0.4878	0.031*

	U11	U22	U33	U12	U13	U23
O1	0.0281 (7)	0.0183 (7)	0.0214 (7)	0.0041 (5)	0.0027 (5)	−0.0041 (5)
O2	0.0417 (9)	0.0379 (9)	0.0209 (7)	0.0093 (7)	0.0037 (6)	−0.0068 (6)
N1	0.0251 (8)	0.0193 (8)	0.0177 (8)	0.0049 (6)	0.0014 (6)	−0.0039 (6)
N2	0.0310 (9)	0.0230 (8)	0.0214 (8)	0.0064 (7)	0.0042 (6)	0.0004 (7)
C1	0.0416 (13)	0.0218 (11)	0.0314 (11)	0.0035 (9)	0.0046 (9)	−0.0050 (9)
C2	0.0272 (10)	0.0194 (10)	0.0277 (10)	0.0035 (8)	0.0003 (8)	−0.0092 (8)
C3	0.0299 (11)	0.0264 (11)	0.0255 (10)	0.0075 (8)	0.0007 (8)	−0.0086 (8)
C4	0.0263 (10)	0.0290 (11)	0.0241 (10)	0.0074 (8)	−0.0002 (8)	−0.0073 (8)
C5	0.0253 (10)	0.0253 (10)	0.0214 (10)	0.0079 (8)	0.0019 (7)	−0.0033 (8)
C6	0.0213 (9)	0.0201 (9)	0.0232 (9)	0.0061 (7)	0.0014 (7)	−0.0036 (7)
C7	0.0280 (10)	0.0278 (10)	0.0227 (10)	0.0083 (8)	0.0037 (7)	−0.0023 (8)
C8	0.0439 (13)	0.0326 (12)	0.0229 (10)	0.0091 (10)	0.0066 (9)	0.0014 (9)
C9	0.0229 (9)	0.0237 (10)	0.0183 (9)	0.0079 (8)	−0.0005 (7)	−0.0049 (7)
C10	0.0295 (10)	0.0215 (10)	0.0243 (10)	0.0057 (8)	0.0018 (8)	−0.0048 (8)
C11	0.0309 (11)	0.0252 (10)	0.0220 (10)	0.0089 (8)	0.0042 (8)	0.0007 (8)
C12	0.0291 (10)	0.0283 (11)	0.0194 (9)	0.0092 (8)	0.0003 (7)	−0.0060 (8)
C13	0.0302 (10)	0.0216 (10)	0.0241 (10)	0.0047 (8)	−0.0014 (8)	−0.0069 (8)
C14	0.0306 (11)	0.0227 (10)	0.0215 (10)	0.0055 (8)	0.0033 (8)	−0.0019 (8)

O1—C6	1.348 (2)	C5—C7	1.418 (3)
O1—C2	1.397 (2)	C7—C8	1.491 (3)
O2—C4	1.240 (2)	C8—H8A	0.9800
N1—C6	1.349 (2)	C8—H8B	0.9800
N1—N2	1.394 (2)	C8—H8C	0.9800
N1—C9	1.428 (2)	C9—C10	1.391 (3)
N2—C7	1.326 (2)	C9—C14	1.396 (3)
C1—C2	1.489 (3)	C10—C11	1.396 (3)
C1—H1A	0.9800	C10—H10	0.9500
C1—H1B	0.9800	C11—C12	1.390 (3)
C1—H1C	0.9800	C11—H11	0.9500
C2—C3	1.336 (3)	C12—C13	1.378 (3)
C3—C4	1.460 (3)	C12—H12	0.9500
C3—H3	0.9500	C13—C14	1.384 (2)
C4—C5	1.447 (3)	C13—H13	0.9500
C5—C6	1.380 (3)	C14—H14	0.9500
C6—O1—C2	114.47 (15)	N2—C7—C8	120.75 (18)
C6—N1—N2	109.07 (14)	C5—C7—C8	128.11 (17)
C6—N1—C9	132.12 (16)	C7—C8—H8A	109.5
N2—N1—C9	118.81 (14)	C7—C8—H8B	109.5
C7—N2—N1	106.27 (15)	H8A—C8—H8B	109.5
C2—C1—H1A	109.5	C7—C8—H8C	109.5
C2—C1—H1B	109.5	H8A—C8—H8C	109.5
H1A—C1—H1B	109.5	H8B—C8—H8C	109.5
C2—C1—H1C	109.5	C10—C9—C14	120.13 (17)
H1A—C1—H1C	109.5	C10—C9—N1	122.27 (16)
H1B—C1—H1C	109.5	C14—C9—N1	117.61 (17)
C3—C2—O1	122.72 (18)	C9—C10—C11	119.17 (18)
C3—C2—C1	126.60 (18)	C9—C10—H10	120.4
O1—C2—C1	110.67 (17)	C11—C10—H10	120.4
C2—C3—C4	124.29 (18)	C12—C11—C10	120.53 (19)
C2—C3—H3	117.9	C12—C11—H11	119.7
C4—C3—H3	117.9	C10—C11—H11	119.7
O2—C4—C5	124.75 (19)	C13—C12—C11	119.72 (18)
O2—C4—C3	123.43 (18)	C13—C12—H12	120.1
C5—C4—C3	111.82 (17)	C11—C12—H12	120.1
C6—C5—C7	104.07 (16)	C12—C13—C14	120.65 (18)
C6—C5—C4	119.77 (18)	C12—C13—H13	119.7
C7—C5—C4	136.14 (18)	C14—C13—H13	119.7
N1—C6—O1	123.63 (16)	C13—C14—C9	119.81 (18)
N1—C6—C5	109.45 (17)	C13—C14—H14	120.1
O1—C6—C5	126.92 (17)	C9—C14—H14	120.1
N2—C7—C5	111.14 (17)
C6—N1—N2—C7	−0.21 (19)	C7—C5—C6—O1	−179.70 (17)
C9—N1—N2—C7	179.19 (15)	C4—C5—C6—O1	−1.3 (3)
C6—O1—C2—C3	−0.3 (3)	N1—N2—C7—C5	0.2 (2)
C6—O1—C2—C1	178.93 (15)	N1—N2—C7—C8	−178.94 (17)
O1—C2—C3—C4	0.7 (3)	C6—C5—C7—N2	−0.2 (2)
C1—C2—C3—C4	−178.48 (18)	C4—C5—C7—N2	−178.2 (2)
C2—C3—C4—O2	179.56 (19)	C6—C5—C7—C8	178.93 (19)
C2—C3—C4—C5	−1.1 (3)	C4—C5—C7—C8	0.9 (4)
O2—C4—C5—C6	−179.34 (18)	C6—N1—C9—C10	−3.8 (3)
C3—C4—C5—C6	1.4 (2)	N2—N1—C9—C10	176.97 (16)
O2—C4—C5—C7	−1.6 (4)	C6—N1—C9—C14	176.32 (19)
C3—C4—C5—C7	179.1 (2)	N2—N1—C9—C14	−2.9 (2)
N2—N1—C6—O1	179.85 (15)	C14—C9—C10—C11	0.7 (3)
C9—N1—C6—O1	0.6 (3)	N1—C9—C10—C11	−179.21 (16)
N2—N1—C6—C5	0.1 (2)	C9—C10—C11—C12	−0.1 (3)
C9—N1—C6—C5	−179.18 (17)	C10—C11—C12—C13	−0.4 (3)
C2—O1—C6—N1	−179.01 (16)	C11—C12—C13—C14	0.2 (3)
C2—O1—C6—C5	0.7 (3)	C12—C13—C14—C9	0.4 (3)
C7—C5—C6—N1	0.0 (2)	C10—C9—C14—C13	−0.8 (3)
C4—C5—C6—N1	178.43 (16)	N1—C9—C14—C13	179.05 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O1	0.95	2.33	2.970 (2)	124
C14—H14···N2	0.95	2.39	2.748 (2)	102
C3—H3···O2i	0.95	2.47	3.400 (3)	167
C8—H8C···O2ii	0.98	2.54	3.472 (3)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯O1	0.95	2.33	2.970 (2)	124
C3—H3⋯O2i	0.95	2.47	3.400 (3)	167
C8—H8C⋯O2ii	0.98	2.54	3.472 (3)	158

Symmetry codes: (i) ; (ii) .