4-[(5R*,10bR*)-2-Methyl-1,10b-dihydro­pyrazolo[1,5-c][1,3]benzoxazin-5-yl]benzoic acid

Kettmann, V.; Světlík, J.

doi:10.1107/S1600536808003607

organic compounds

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Volume 64| Part 3| March 2008| Page o563

doi:10.1107/S1600536808003607

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4-[(5R,10bR)-2-Methyl-1,10b-dihydropyrazolo[1,5-c][1,3]benzoxazin-5-yl]benzoic acid

Viktor Kettmann ^a ^* and Jan Světlík ^a

^aFaculty of Pharmacy, Comenius University, Odbojarov 10, SK-83232 Bratislava, Slovakia
^*Correspondence e-mail: kettmann@fpharm.uniba.sk

(Received 25 January 2008; accepted 1 February 2008; online 6 February 2008)

In the title compound, C₁₈H₁₆N₂O₃, a potential inhibitor of the cyclooxygenase-2 isoenzyme, the pyrazoline ring exists in a flattened envelope conformation with one C atom deviating by 0.463 Å from the mean plane of the remaining four atoms. The puckering of the central oxazine ring is more severe, with one N atom and one C atom displaced by 0.235 (6) and 0.370 (2) Å, respectively, on opposite sides of the mean plane defined by the other four atoms; the conformation is that of a half-chair. As a result, the molecule as a whole is not planar. The carboxyl group is involved in an intermolecular O—H⋯N hydrogen bond, which links the molecules into centrosymmetric dimers.

Related literature

For related literature, see: Palomer et al. (2002 ); Subbaramaiah et al. (2002 ); Světlík et al. (2005 ).

Experimental

Crystal data

C₁₈H₁₆N₂O₃
M_r = 308.33
Triclinic, $[P \overline 1]$
a = 6.638 (2) Å
b = 10.997 (3) Å
c = 11.141 (3) Å
α = 70.78 (2)°
β = 80.85 (3)°
γ = 79.15 (2)°
V = 750.1 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 (2) K
0.30 × 0.20 × 0.15 mm

Data collection

Siemens P4 diffractometer
Absorption correction: none
5341 measured reflections
4312 independent reflections
3216 reflections with I > 2σ(I)
R_int = 0.019
3 standard reflections every 97 reflections intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.152
S = 1.01
4312 reflections
210 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O8—H8A⋯N3ⁱ	0.82	1.93	2.7356 (17)	168
Symmetry code: (i) -x-1, -y+1, -z+1.

Data collection: XSCANS (Siemens, 1991 ); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808003607/bi2280sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808003607/bi2280Isup2.hkl

checkCIF report

Comment top

Recently, based on a pharmacophoric model of the cyclooxygenase-2 (COX-2) inhibitors (Palomer et al., 2002) as novel anticancer drugs (Subbaramaiah et al., 2002), we designed and prepared a series of 2- and 5-substituted derivatives containing the tricyclic system shown in Fig. 1. In order to recognize enzyme binding requirements for this fused heterocycle, we selected the 2-methyl-5-carboxyphenyl derivative, for single-crystal X-ray analysis. The compound was obtained as a 1:1 mixture of the cis (1a) and trans (1 b) diastereomers and we report here the structure of the cis isomer.

The molecular structure and atom-numbering scheme is shown in Fig. 2. Bond distances and angles are close to those generally expected. The atom O6 is essentially sp²-hybridized and involved in conjugation with the benzo ring as indicated by the valence angle at this atom and a non-equivalency of the O6—C5 and O6—C7 bonds.

The most interesting feature of the structure—the spatial relationship between the pharmacophoric elements (hydrophobic groups and H-bond donors/acceptors)—is given by conformation of the (partially) saturated rings. Thus, the pyrazoline ring adopts a flat-envelope conformation with atom C13 (at the flap) deviating by 0.463 Å from the mean plane of the remaining atoms. The central oxazine ring is also non-planar and is puckered in such a manner that the four atoms O6, C7, C12 and C13 are planar to within 0.006 (2) Å, while atoms N4 and C5 are displaced by 0.235 (6) and 0.370 (2) Å, respectively, on opposite sides of the plane. As a result of the relatively severe puckering of the central ring, the molecule as a whole is non-planar but consists of two approximately planar segments, C5/O6/C7–C13 and C13/C1/C2/N3/N4/C5, folded about the C5···C13 line [dihedral angle 71.7 (1)°]. The carboxyphenyl substituent is rotated by 39.8 (1)° from the mean plane of the oxazine ring.

The crystal packing is dominated by a hydrogen bond between centrosymmetrically related molecules (Table 1) which result in formation of hydrogen-bonded dimers.

Related literature top

For related literature, see: Palomer et al. (2002); Subbaramaiah et al. (2002); Světlík et al. (2005).

Experimental top

Synthesis of the title compound has been described previously (Světlík et al., 2005). In short, a solution of 4-carboxybenzaldehyde (0.30 g, 2 mmol) and pyrazoline (0.35 g, 2 mmol) in ethyl acetate (14 ml) and methanol (1 ml) was left to react at room temperature for 1 h. The resulting precipitate was filtered off and crystallized from ethanol to obtain (1a) (70% yield; m.p. 474–480 K) as colourless crystals. Crystals suitable for the X-ray analysis were obtained by slow crystallization from acetone.

Computing details top

Data collection: XSCANS (Siemens, 1991); cell refinement: XSCANS (Siemens, 1991); data reduction: XSCANS (Siemens, 1991); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The cis title compound (1a) and its trans isomer (1 b).
	Fig. 2. Molecular structure with displacement ellipsoids drawn at 35% probability for non-H atoms.

4-[(5R*,10bR*)-2-Methyl-1,10b-dihydropyrazolo[1,5-c][1,3]benzoxazin-5-yl]benzoic acid top

Crystal data top

C₁₈H₁₆N₂O₃	Z = 2
M_r = 308.33	F(000) = 324
Triclinic, P1	D_x = 1.365 Mg m⁻³
Hall symbol: -P 1	Melting point: 477 K
a = 6.638 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.997 (3) Å	Cell parameters from 20 reflections
c = 11.141 (3) Å	θ = 7–18°
α = 70.78 (2)°	µ = 0.09 mm⁻¹
β = 80.85 (3)°	T = 296 K
γ = 79.15 (2)°	Prism, colourless
V = 750.1 (4) Å³	0.30 × 0.20 × 0.15 mm

Data collection top

Siemens P4 diffractometer	R_int = 0.019
Radiation source: fine-focus sealed tube	θ_max = 30.0°, θ_min = 2.0°
Graphite monochromator	h = −1→9
ω/2θ scans	k = −14→14
5341 measured reflections	l = −15→15
4312 independent reflections	3 standard reflections every 97 reflections
3216 reflections with I > 2σ(I)	intensity decay: none

Refinement top

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.152	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0853P)² + 0.0987P] where P = (F_o² + 2F_c²)/3
4312 reflections	(Δ/σ)_max = 0.001
210 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₈H₁₆N₂O₃	γ = 79.15 (2)°
M_r = 308.33	V = 750.1 (4) Å³
Triclinic, P1	Z = 2
a = 6.638 (2) Å	Mo Kα radiation
b = 10.997 (3) Å	µ = 0.09 mm⁻¹
c = 11.141 (3) Å	T = 296 K
α = 70.78 (2)°	0.30 × 0.20 × 0.15 mm
β = 80.85 (3)°

Data collection top

Siemens P4 diffractometer	R_int = 0.019
5341 measured reflections	3 standard reflections every 97 reflections
4312 independent reflections	intensity decay: none
3216 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.152	H-atom parameters constrained
S = 1.01	Δρ_max = 0.29 e Å⁻³
4312 reflections	Δρ_min = −0.22 e Å⁻³
210 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.3065 (2)	0.63515 (13)	0.03856 (13)	0.0364 (3)
H1A	0.3369	0.6320	−0.0485	0.044*
H1B	0.4338	0.6149	0.0780	0.044*
C2	0.1553 (2)	0.54630 (12)	0.11427 (12)	0.0324 (3)
N3	0.01255 (17)	0.59887 (10)	0.18002 (10)	0.0314 (2)
N4	0.05040 (17)	0.72620 (10)	0.16410 (10)	0.0304 (2)
C5	−0.1328 (2)	0.81721 (13)	0.17228 (12)	0.0342 (3)
H5	−0.0911	0.8976	0.1736	0.041*
O6	−0.25382 (16)	0.84950 (11)	0.06661 (9)	0.0440 (3)
C7	−0.1451 (2)	0.87381 (13)	−0.05137 (12)	0.0371 (3)
C8	−0.2589 (3)	0.93655 (15)	−0.15442 (14)	0.0479 (4)
H8	−0.3999	0.9630	−0.1409	0.057*
C9	−0.1623 (3)	0.95933 (18)	−0.27641 (16)	0.0586 (5)
H9	−0.2381	1.0010	−0.3458	0.070*
C10	0.0466 (3)	0.92058 (17)	−0.29635 (15)	0.0560 (5)
H10	0.1116	0.9354	−0.3792	0.067*
C11	0.1589 (3)	0.86000 (14)	−0.19372 (13)	0.0449 (4)
H11	0.3003	0.8352	−0.2079	0.054*
C12	0.0646 (2)	0.83525 (12)	−0.06896 (12)	0.0347 (3)
C13	0.1871 (2)	0.76641 (13)	0.04385 (12)	0.0330 (3)
H13	0.2808	0.8222	0.0510	0.040*
C14	0.1724 (2)	0.40903 (14)	0.11858 (15)	0.0418 (3)
H14A	0.2925	0.3598	0.1589	0.063*
H14B	0.1840	0.4044	0.0332	0.063*
H14C	0.0517	0.3737	0.1665	0.063*
C15	−0.2727 (2)	0.76809 (12)	0.29245 (12)	0.0329 (3)
C16	−0.2086 (2)	0.75161 (17)	0.40981 (14)	0.0448 (4)
H16	−0.0830	0.7752	0.4137	0.054*
C17	−0.3307 (3)	0.70033 (17)	0.52093 (14)	0.0462 (4)
H17	−0.2865	0.6890	0.5995	0.055*
C18	−0.5184 (2)	0.66557 (13)	0.51636 (12)	0.0342 (3)
C19	−0.5837 (2)	0.68431 (14)	0.39930 (13)	0.0374 (3)
H19	−0.7103	0.6621	0.3952	0.045*
C20	−0.4614 (2)	0.73595 (14)	0.28820 (13)	0.0381 (3)
H20	−0.5070	0.7492	0.2096	0.046*
C21	−0.6403 (2)	0.60087 (13)	0.63696 (13)	0.0361 (3)
O7	−0.5895 (2)	0.58142 (13)	0.74163 (10)	0.0520 (3)
O8	−0.80628 (16)	0.56450 (11)	0.61698 (10)	0.0454 (3)
H8A	−0.8571	0.5179	0.6845	0.068*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0382 (7)	0.0364 (7)	0.0318 (6)	−0.0088 (5)	0.0038 (5)	−0.0084 (5)
C2	0.0362 (6)	0.0317 (6)	0.0286 (6)	−0.0074 (5)	−0.0017 (5)	−0.0077 (5)
N3	0.0364 (6)	0.0285 (5)	0.0281 (5)	−0.0088 (4)	−0.0002 (4)	−0.0065 (4)
N4	0.0362 (5)	0.0290 (5)	0.0256 (5)	−0.0104 (4)	0.0017 (4)	−0.0072 (4)
C5	0.0423 (7)	0.0310 (6)	0.0282 (6)	−0.0086 (5)	0.0016 (5)	−0.0082 (5)
O6	0.0434 (5)	0.0498 (6)	0.0273 (5)	−0.0018 (5)	−0.0005 (4)	−0.0009 (4)
C7	0.0514 (8)	0.0290 (6)	0.0273 (6)	−0.0098 (6)	−0.0004 (5)	−0.0034 (5)
C8	0.0585 (9)	0.0417 (8)	0.0359 (7)	−0.0042 (7)	−0.0097 (7)	−0.0015 (6)
C9	0.0890 (14)	0.0478 (9)	0.0316 (7)	−0.0059 (9)	−0.0143 (8)	−0.0009 (6)
C10	0.0856 (13)	0.0474 (9)	0.0279 (7)	−0.0115 (9)	0.0037 (8)	−0.0058 (6)
C11	0.0624 (9)	0.0362 (7)	0.0313 (7)	−0.0126 (7)	0.0087 (6)	−0.0072 (5)
C12	0.0507 (8)	0.0253 (6)	0.0270 (6)	−0.0126 (5)	0.0018 (5)	−0.0055 (4)
C13	0.0368 (6)	0.0331 (6)	0.0288 (6)	−0.0134 (5)	0.0036 (5)	−0.0079 (5)
C14	0.0464 (8)	0.0351 (7)	0.0449 (8)	−0.0074 (6)	−0.0004 (6)	−0.0149 (6)
C15	0.0403 (7)	0.0287 (6)	0.0276 (6)	−0.0059 (5)	0.0024 (5)	−0.0081 (5)
C16	0.0447 (8)	0.0600 (9)	0.0340 (7)	−0.0227 (7)	0.0018 (6)	−0.0147 (6)
C17	0.0524 (9)	0.0628 (10)	0.0270 (6)	−0.0203 (7)	−0.0002 (6)	−0.0139 (6)
C18	0.0396 (7)	0.0322 (6)	0.0289 (6)	−0.0055 (5)	0.0031 (5)	−0.0098 (5)
C19	0.0359 (7)	0.0410 (7)	0.0329 (6)	−0.0087 (5)	−0.0014 (5)	−0.0076 (5)
C20	0.0426 (7)	0.0417 (7)	0.0277 (6)	−0.0085 (6)	−0.0042 (5)	−0.0063 (5)
C21	0.0405 (7)	0.0337 (6)	0.0311 (6)	−0.0055 (5)	0.0038 (5)	−0.0097 (5)
O7	0.0637 (7)	0.0646 (7)	0.0285 (5)	−0.0204 (6)	0.0024 (5)	−0.0126 (5)
O8	0.0457 (6)	0.0506 (6)	0.0336 (5)	−0.0165 (5)	0.0032 (4)	−0.0029 (4)

Geometric parameters (Å, º) top

C1—C2	1.4934 (19)	C11—C12	1.3915 (19)
C1—C13	1.5249 (19)	C11—H11	0.930
C1—H1A	0.970	C12—C13	1.5101 (19)
C1—H1B	0.970	C13—H13	0.980
C2—N3	1.2730 (17)	C14—H14A	0.960
C2—C14	1.4776 (19)	C14—H14B	0.960
N3—N4	1.4178 (15)	C14—H14C	0.960
N4—C5	1.4335 (18)	C15—C20	1.376 (2)
N4—C13	1.4793 (17)	C15—C16	1.3839 (19)
C5—O6	1.4409 (17)	C16—C17	1.379 (2)
C5—C15	1.5047 (18)	C16—H16	0.930
C5—H5	0.980	C17—C18	1.384 (2)
O6—C7	1.3637 (17)	C17—H17	0.930
C7—C12	1.379 (2)	C18—C19	1.3783 (19)
C7—C8	1.387 (2)	C18—C21	1.4856 (19)
C8—C9	1.371 (2)	C19—C20	1.380 (2)
C8—H8	0.930	C19—H19	0.930
C9—C10	1.377 (3)	C20—H20	0.930
C9—H9	0.930	C21—O7	1.2053 (17)
C10—C11	1.375 (2)	C21—O8	1.3140 (18)
C10—H10	0.930	O8—H8A	0.820

C2—C1—C13	100.79 (11)	C7—C12—C13	120.90 (12)
C2—C1—H1A	111.6	C11—C12—C13	121.16 (14)
C13—C1—H1A	111.6	N4—C13—C12	111.46 (11)
C2—C1—H1B	111.6	N4—C13—C1	100.98 (10)
C13—C1—H1B	111.6	C12—C13—C1	112.93 (11)
H1A—C1—H1B	109.4	N4—C13—H13	110.4
N3—C2—C14	122.55 (13)	C12—C13—H13	110.4
N3—C2—C1	113.23 (12)	C1—C13—H13	110.4
C14—C2—C1	124.16 (12)	C2—C14—H14A	109.5
C2—N3—N4	108.71 (11)	C2—C14—H14B	109.5
N3—N4—C5	114.05 (10)	H14A—C14—H14B	109.5
N3—N4—C13	107.26 (9)	C2—C14—H14C	109.5
C5—N4—C13	114.20 (10)	H14A—C14—H14C	109.5
N4—C5—O6	113.73 (11)	H14B—C14—H14C	109.5
N4—C5—C15	112.11 (11)	C20—C15—C16	119.21 (13)
O6—C5—C15	106.99 (11)	C20—C15—C5	121.22 (12)
N4—C5—H5	107.9	C16—C15—C5	119.55 (13)
O6—C5—H5	107.9	C17—C16—C15	120.12 (14)
C15—C5—H5	107.9	C17—C16—H16	119.9
C7—O6—C5	115.49 (11)	C15—C16—H16	119.9
O6—C7—C12	122.64 (12)	C16—C17—C18	120.50 (13)
O6—C7—C8	116.04 (14)	C16—C17—H17	119.8
C12—C7—C8	121.29 (14)	C18—C17—H17	119.8
C9—C8—C7	119.60 (17)	C19—C18—C17	119.28 (13)
C9—C8—H8	120.2	C19—C18—C21	120.86 (13)
C7—C8—H8	120.2	C17—C18—C21	119.74 (13)
C8—C9—C10	120.15 (16)	C18—C19—C20	120.10 (13)
C8—C9—H9	119.9	C18—C19—H19	119.9
C10—C9—H9	119.9	C20—C19—H19	119.9
C11—C10—C9	119.92 (15)	C15—C20—C19	120.77 (13)
C11—C10—H10	120.0	C15—C20—H20	119.6
C9—C10—H10	120.0	C19—C20—H20	119.6
C10—C11—C12	121.10 (16)	O7—C21—O8	123.78 (13)
C10—C11—H11	119.4	O7—C21—C18	123.50 (14)
C12—C11—H11	119.4	O8—C21—C18	112.71 (12)
C7—C12—C11	117.93 (14)	C21—O8—H8A	109.5

C13—C1—C2—N3	−15.79 (15)	N3—N4—C13—C1	−29.67 (12)
C13—C1—C2—C14	166.98 (12)	C5—N4—C13—C1	−157.08 (11)
C14—C2—N3—N4	174.46 (11)	C7—C12—C13—N4	11.07 (17)
C1—C2—N3—N4	−2.82 (15)	C11—C12—C13—N4	−167.94 (12)
C2—N3—N4—C5	148.89 (11)	C7—C12—C13—C1	123.94 (13)
C2—N3—N4—C13	21.40 (13)	C11—C12—C13—C1	−55.08 (17)
N3—N4—C5—O6	−68.94 (13)	C2—C1—C13—N4	26.12 (12)
C13—N4—C5—O6	54.89 (15)	C2—C1—C13—C12	−93.01 (13)
N3—N4—C5—C15	52.60 (14)	N4—C5—C15—C20	−112.18 (15)
C13—N4—C5—C15	176.43 (10)	O6—C5—C15—C20	13.15 (17)
N4—C5—O6—C7	−44.40 (16)	N4—C5—C15—C16	66.12 (17)
C15—C5—O6—C7	−168.75 (11)	O6—C5—C15—C16	−168.55 (12)
C5—O6—C7—C12	17.97 (19)	C20—C15—C16—C17	1.7 (2)
C5—O6—C7—C8	−164.03 (12)	C5—C15—C16—C17	−176.64 (14)
O6—C7—C8—C9	−177.12 (14)	C15—C16—C17—C18	−0.4 (3)
C12—C7—C8—C9	0.9 (2)	C16—C17—C18—C19	−0.8 (2)
C7—C8—C9—C10	−0.3 (3)	C16—C17—C18—C21	175.18 (15)
C8—C9—C10—C11	−0.6 (3)	C17—C18—C19—C20	0.7 (2)
C9—C10—C11—C12	0.9 (3)	C21—C18—C19—C20	−175.28 (13)
O6—C7—C12—C11	177.24 (13)	C16—C15—C20—C19	−1.9 (2)
C8—C7—C12—C11	−0.7 (2)	C5—C15—C20—C19	176.45 (13)
O6—C7—C12—C13	−1.8 (2)	C18—C19—C20—C15	0.7 (2)
C8—C7—C12—C13	−179.70 (13)	C19—C18—C21—O7	179.54 (14)
C10—C11—C12—C7	−0.2 (2)	C17—C18—C21—O7	3.6 (2)
C10—C11—C12—C13	178.82 (14)	C19—C18—C21—O8	1.05 (19)
N3—N4—C13—C12	90.51 (12)	C17—C18—C21—O8	−174.89 (13)
C5—N4—C13—C12	−36.89 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O8—H8A···N3ⁱ	0.82	1.93	2.7356 (17)	168

Symmetry code: (i) −x−1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₆N₂O₃
M_r	308.33
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	6.638 (2), 10.997 (3), 11.141 (3)
α, β, γ (°)	70.78 (2), 80.85 (3), 79.15 (2)
V (Å³)	750.1 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.20 × 0.15

Data collection
Diffractometer	Siemens P4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	5341, 4312, 3216
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.152, 1.01
No. of reflections	4312
No. of parameters	210
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.22

Computer programs: XSCANS (Siemens, 1991), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O8—H8A···N3ⁱ	0.82	1.93	2.7356 (17)	167.7

Symmetry code: (i) −x−1, −y+1, −z+1.

Acknowledgements

This work was supported by the Grant Agency of the Slovak Republic, project Nos. 1/4298/07 and 1/4299/07.

References

Palomer, A., Cabré, F., Pascual, J., Campos, J., Trujillo, M. A., Entrena, A., Gallo, M. A., Garcia, L., Mauleón, D. & Espinosa, A. (2002). J. Med. Chem. 45, 1402–1411. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1991). XSCANS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Subbaramaiah, K., Norton, L., Gerald, W. & Dannenberg, A. J. (2002). J. Biol. Chem. 277, 18649–18659. Web of Science CrossRef PubMed CAS Google Scholar
Světlík, J., Pronayova, N. & Kubista, J. (2005). J. Heterocycl. Chem. 42, 1143–1147. Google Scholar

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Volume 64| Part 3| March 2008| Page o563

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

4-[(5R*,10bR*)-2-Methyl-1,10b-di­hydro­pyrazolo[1,5-c][1,3]benzoxazin-5-yl]benzoic acid

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

4-[(5R,10bR)-2-Methyl-1,10b-dihydropyrazolo[1,5-c][1,3]benzoxazin-5-yl]benzoic acid