rac-1-[6-Hy­droxy-4-(4-meth­oxy­phen­yl)-3,6-dimethyl-4,5,6,7-tetra­hydro-2H-indazol-5-yl]ethanone

Potekhin, K.A.; Askerov, R.K.; Hajiyeva, K.E.; Gadirova, N.A.; Nazarov, S.I.

doi:10.1107/S1600536813000937

organic compounds

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ISSN: 2056-9890

Volume 69| Part 2| February 2013| Page o243

doi:10.1107/S1600536813000937

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rac-1-[6-Hydroxy-4-(4-methoxyphenyl)-3,6-dimethyl-4,5,6,7-tetrahydro-2H-indazol-5-yl]ethanone

Konstantin A. Potekhin,^a Rizvan K. Askerov,^b Kushvar E. Hajiyeva,^b Narmina A. Gadirova ^b ^* and Shahkaram I. Nazarov ^b

^aVladimir State University, Qor'ky St 87, 600000 Vladimir, Russian Federation, and ^bBaku State University, Z. Khalilov St 23, AZ-1148 Baku, Azerbaijan
^*Correspondence e-mail: Naralab7@gmail.com

(Received 30 November 2012; accepted 10 January 2013; online 16 January 2013)

The title compound, C₁₈H₂₂N₂O₃, represents a (4S,5R,6S)-stereoisomer, crystallizing as a racemate in a centrosymmetric space group. The six-membered aliphatic ring adopts a half-chair conformation, with the hydroxy- and acetyl-substituted C atoms deviating by 0.458 (2) and −0.366 (2) Å, respectively, from the plane defined by other four ring atoms. The pyrazole ring is essentially planar [r.m.s deviation = 0.004 (2) Å]. In the crystal, the molecules are linked into chains along the b axis by N—H⋯N hydrogen bonds. The chains are linked by O—H⋯N hydrogen bonds into layers parallel to the bc plane.

Related literature

For background to the use of β-cycloketols as synthons in the synthesis of pyrazoles, see: Pramula et al. (1985 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For ring conformations, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₁₈H₂₂N₂O₃
M_r = 314.38
Monoclinic, P 2₁ /c
a = 18.3693 (14) Å
b = 5.6971 (4) Å
c = 16.3049 (12) Å
β = 109.526 (1)°
V = 1608.2 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.974, T_max = 0.982
17994 measured reflections
4015 independent reflections
2740 reflections with I > 2σ(I)
R_int = 0.053

Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.151
S = 1.00
4015 reflections
220 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯N2ⁱ	0.81 (3)	2.15 (3)	2.948 (2)	168 (2)
N1—H1N⋯N2ⁱⁱ	0.87 (2)	2.27 (2)	3.093 (2)	157 (2)
Symmetry codes: (i) -x+1, -y, -z+1; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT-Plus (Bruker, 2001 ); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813000937/ld2089sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813000937/ld2089Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813000937/ld2089Isup3.cml

checkCIF report

Comment top

We explore the use of simple molecules with different functionalities for synthesis of heterocycles. Particularly, the β-cycloketols have been used as an effective synthon in syntheses of pyrazoles (Pramula et al. 1985).

Fig. 1 shows the molecular structure of title compound (I), C₁₈H₂₂N₂O₃. The six-membered ring C₁, C₂, C₃, C₄, C₅, C₆ has a half-chair conformation. Four atoms of a six-membered ring C₁,C₂, C₅, C₆ are located on the same plane within 0.004 (2) Å while C₃ (+ 0.458 (2) Å) and C₄ (- 0.366 (2) Å) atoms are deviating to the opposite sides of the plane. The pyrazole ring is essentially planar (r.m.s deviation is 0.004 (2) Å). Hydrogen bonds N—H ··· N combine molecules into chains oriented along the axis b (Fig.2). H-bonds O—H ··· N form centrosymmetric cycles. Through these cycles, the above chains are combined into two-dimensional layers parallel to the plane bc.

Related literature top

For background to the use of β-cycloketols as synthons in the synthesis of pyrazoles, see: Pramula et al. (1985). For hydrogen-bond motifs, see: Bernstein et al. (1995). For ring conformations, see: Cremer & Pople (1975).

Experimental top

2,4-Diacetyl-5-hydroxy-5-metyl-3(4-methoxyphenyl)cyclohexanone (20 mmol) and hydrazine hydrate (20 mmol) were dissolved in 20 ml of ethanol. The mixture was stirred at 335–340 K for 10 h. After cooling to the room temperature, white crystals were obtained. The crystals were filtered off and washed with cold ethanol. Then they were dissolved in ethanol (50 ml) and recrystallized to yield colourless block-shaped crystals suitable for data collection.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with the atomic numbering scheme. Non-essential H-atoms were removed for clarity. Displacement ellipsoids were drawn at 50% probability.
	Fig. 2. The projection of the crystal structure (I) along the b axis. H bonds are shown as a dashed lines. H atoms not involved in the formation of the hydrogen bonds are not shown.

rac-1-[6-Hydroxy-4-(4-methoxyphenyl)-3,6-dimethyl-4,5,6,7- tetrahydro-2H-indazol-5-yl]ethanone top

Crystal data top

C₁₈H₂₂N₂O₃	F(000) = 672
M_r = 314.38	D_x = 1.298 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2645 reflections
a = 18.3693 (14) Å	θ = 2.4–27.8°
b = 5.6971 (4) Å	µ = 0.09 mm⁻¹
c = 16.3049 (12) Å	T = 296 K
β = 109.526 (1)°	Prism, yellow
V = 1608.2 (2) Å³	0.30 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	4015 independent reflections
Radiation source: fine-focus sealed tube	2740 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.053
ϕ and ω scans	θ_max = 28.4°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −24→24
T_min = 0.974, T_max = 0.982	k = −7→7
17994 measured reflections	l = −21→21

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)] = 0.057	Hydrogen site location: difference Fourier map
wR(F²) = 0.151	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.0775P)² + 0.4526P] where P = (F_o² + 2F_c²)/3
4015 reflections	(Δ/σ)_max < 0.001
220 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₈H₂₂N₂O₃	V = 1608.2 (2) Å³
M_r = 314.38	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 18.3693 (14) Å	µ = 0.09 mm⁻¹
b = 5.6971 (4) Å	T = 296 K
c = 16.3049 (12) Å	0.30 × 0.20 × 0.20 mm
β = 109.526 (1)°

Data collection top

Bruker APEXII CCD diffractometer	4015 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	2740 reflections with I > 2σ(I)
T_min = 0.974, T_max = 0.982	R_int = 0.053
17994 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	0 restraints
wR(F²) = 0.151	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.28 e Å⁻³
4015 reflections	Δρ_min = −0.26 e Å⁻³
220 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
O1	0.37902 (8)	0.0325 (2)	0.39112 (9)	0.0292 (3)
H1O	0.4175 (15)	0.014 (4)	0.3782 (15)	0.042 (7)*
O2	0.17526 (9)	−0.3321 (3)	0.33143 (10)	0.0509 (5)
O3	0.02786 (9)	0.2338 (3)	0.60541 (12)	0.0581 (5)
N1	0.44992 (10)	0.1360 (3)	0.68991 (11)	0.0323 (4)
H1N	0.4757 (13)	0.189 (4)	0.7417 (15)	0.036 (6)*
N2	0.47720 (9)	−0.0401 (3)	0.65158 (10)	0.0317 (4)
C1	0.41943 (10)	−0.0765 (3)	0.57672 (11)	0.0250 (4)
C2	0.42242 (11)	−0.2495 (3)	0.50915 (12)	0.0291 (4)
H2B	0.4132	−0.4062	0.5267	0.035*
H2C	0.4732	−0.2469	0.5033	0.035*
C3	0.36087 (10)	−0.1881 (3)	0.42137 (11)	0.0240 (4)
C4	0.28224 (10)	−0.1512 (3)	0.43618 (11)	0.0233 (4)
H4A	0.2756	−0.2845	0.4710	0.028*
C5	0.28328 (10)	0.0725 (3)	0.49055 (11)	0.0224 (4)
H5A	0.2854	0.2083	0.4545	0.027*
C6	0.35664 (10)	0.0713 (3)	0.56806 (11)	0.0236 (4)
C7	0.37853 (10)	0.2084 (3)	0.64195 (12)	0.0274 (4)
C8	0.35771 (13)	−0.3796 (4)	0.35532 (13)	0.0359 (5)
H8A	0.4077	−0.3967	0.3494	0.054*
H8B	0.3206	−0.3377	0.3001	0.054*
H8C	0.3428	−0.5252	0.3748	0.054*
C9	0.21385 (11)	−0.1556 (4)	0.35177 (12)	0.0296 (4)
C10	0.19493 (14)	0.0554 (4)	0.29457 (13)	0.0429 (5)
H10A	0.1628	0.0102	0.2372	0.064*
H10B	0.2418	0.1242	0.2919	0.064*
H10C	0.1681	0.1676	0.3178	0.064*
C11	0.21160 (10)	0.0998 (3)	0.51714 (11)	0.0241 (4)
C12	0.16362 (11)	0.2925 (4)	0.49013 (13)	0.0327 (4)
H12A	0.1726	0.3980	0.4511	0.039*
C13	0.10256 (12)	0.3313 (4)	0.52006 (15)	0.0404 (5)
H13A	0.0713	0.4625	0.5014	0.048*
C14	0.08796 (11)	0.1756 (4)	0.57763 (14)	0.0366 (5)
C15	0.13375 (13)	−0.0199 (4)	0.60398 (15)	0.0406 (5)
H15A	0.1237	−0.1274	0.6418	0.049*
C16	0.19500 (12)	−0.0552 (4)	0.57368 (14)	0.0368 (5)
H16A	0.2259	−0.1873	0.5920	0.044*
C17	0.00859 (16)	0.0772 (6)	0.66259 (19)	0.0634 (8)
H17A	−0.0343	0.1391	0.6768	0.095*
H17B	0.0522	0.0593	0.7149	0.095*
H17C	−0.0051	−0.0727	0.6348	0.095*
C18	0.33930 (13)	0.4034 (4)	0.67129 (14)	0.0416 (5)
H18A	0.3487	0.3891	0.7326	0.062*
H18B	0.2847	0.3962	0.6406	0.062*
H18C	0.3591	0.5510	0.6596	0.062*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0287 (7)	0.0281 (7)	0.0358 (7)	0.0006 (6)	0.0173 (6)	0.0041 (6)
O2	0.0481 (10)	0.0498 (10)	0.0436 (9)	−0.0213 (8)	0.0006 (7)	−0.0046 (8)
O3	0.0388 (9)	0.0800 (13)	0.0677 (11)	0.0212 (9)	0.0342 (8)	0.0121 (10)
N1	0.0282 (9)	0.0422 (10)	0.0218 (8)	0.0005 (7)	0.0023 (7)	−0.0050 (7)
N2	0.0244 (8)	0.0415 (10)	0.0266 (8)	0.0043 (7)	0.0049 (7)	0.0006 (7)
C1	0.0211 (9)	0.0299 (10)	0.0240 (9)	0.0020 (7)	0.0074 (7)	0.0029 (7)
C2	0.0266 (9)	0.0295 (10)	0.0316 (10)	0.0059 (8)	0.0101 (8)	0.0004 (8)
C3	0.0249 (9)	0.0237 (9)	0.0245 (9)	0.0008 (7)	0.0096 (7)	−0.0002 (7)
C4	0.0229 (9)	0.0255 (9)	0.0217 (8)	−0.0025 (7)	0.0074 (7)	0.0017 (7)
C5	0.0199 (8)	0.0247 (9)	0.0220 (8)	0.0016 (7)	0.0063 (7)	0.0022 (7)
C6	0.0225 (9)	0.0277 (9)	0.0218 (8)	0.0003 (7)	0.0087 (7)	0.0003 (7)
C7	0.0255 (9)	0.0339 (10)	0.0218 (9)	0.0008 (8)	0.0067 (7)	0.0001 (8)
C8	0.0416 (12)	0.0330 (11)	0.0361 (11)	−0.0005 (9)	0.0169 (9)	−0.0083 (9)
C9	0.0264 (9)	0.0381 (11)	0.0257 (9)	−0.0038 (8)	0.0106 (8)	−0.0045 (8)
C10	0.0413 (12)	0.0506 (14)	0.0284 (10)	−0.0003 (10)	0.0006 (9)	0.0047 (10)
C11	0.0196 (8)	0.0281 (9)	0.0227 (8)	0.0012 (7)	0.0045 (7)	−0.0006 (7)
C12	0.0287 (10)	0.0326 (11)	0.0360 (10)	0.0038 (8)	0.0098 (8)	0.0062 (9)
C13	0.0284 (10)	0.0418 (12)	0.0500 (13)	0.0158 (9)	0.0120 (9)	0.0071 (10)
C14	0.0247 (10)	0.0484 (13)	0.0388 (11)	0.0053 (9)	0.0133 (9)	−0.0028 (10)
C15	0.0384 (12)	0.0461 (13)	0.0440 (12)	0.0059 (9)	0.0227 (10)	0.0142 (10)
C16	0.0358 (11)	0.0355 (11)	0.0439 (12)	0.0133 (9)	0.0198 (9)	0.0129 (9)
C17	0.0423 (14)	0.094 (2)	0.0652 (17)	−0.0028 (14)	0.0330 (13)	−0.0015 (16)
C18	0.0427 (12)	0.0475 (13)	0.0321 (11)	0.0069 (10)	0.0091 (9)	−0.0116 (10)

Geometric parameters (Å, º) top

O1—C3	1.430 (2)	C8—H8A	0.9600
O1—H1O	0.81 (3)	C8—H8B	0.9600
O2—C9	1.211 (2)	C8—H8C	0.9600
O3—C14	1.367 (2)	C9—C10	1.489 (3)
O3—C17	1.418 (3)	C10—H10A	0.9600
N1—C7	1.348 (2)	C10—H10B	0.9600
N1—N2	1.363 (2)	C10—H10C	0.9600
N1—H1N	0.87 (2)	C11—C16	1.382 (3)
N2—C1	1.339 (2)	C11—C12	1.385 (3)
C1—C6	1.397 (2)	C12—C13	1.382 (3)
C1—C2	1.493 (3)	C12—H12A	0.9300
C2—C3	1.539 (3)	C13—C14	1.382 (3)
C2—H2B	0.9700	C13—H13A	0.9300
C2—H2C	0.9700	C14—C15	1.375 (3)
C3—C8	1.520 (3)	C15—C16	1.386 (3)
C3—C4	1.556 (2)	C15—H15A	0.9300
C4—C9	1.522 (2)	C16—H16A	0.9300
C4—C5	1.549 (2)	C17—H17A	0.9600
C4—H4A	0.9800	C17—H17B	0.9600
C5—C6	1.508 (2)	C17—H17C	0.9600
C5—C11	1.525 (2)	C18—H18A	0.9600
C5—H5A	0.9800	C18—H18B	0.9600
C6—C7	1.378 (3)	C18—H18C	0.9600
C7—C18	1.488 (3)

C3—O1—H1O	107.3 (17)	C3—C8—H8C	109.5
C14—O3—C17	118.17 (19)	H8A—C8—H8C	109.5
C7—N1—N2	113.26 (16)	H8B—C8—H8C	109.5
C7—N1—H1N	124.4 (15)	O2—C9—C10	120.39 (18)
N2—N1—H1N	122.3 (15)	O2—C9—C4	119.46 (18)
C1—N2—N1	103.36 (15)	C10—C9—C4	120.14 (17)
N2—C1—C6	112.02 (16)	C9—C10—H10A	109.5
N2—C1—C2	124.16 (16)	C9—C10—H10B	109.5
C6—C1—C2	123.80 (16)	H10A—C10—H10B	109.5
C1—C2—C3	109.87 (14)	C9—C10—H10C	109.5
C1—C2—H2B	109.7	H10A—C10—H10C	109.5
C3—C2—H2B	109.7	H10B—C10—H10C	109.5
C1—C2—H2C	109.7	C16—C11—C12	117.36 (17)
C3—C2—H2C	109.7	C16—C11—C5	121.89 (16)
H2B—C2—H2C	108.2	C12—C11—C5	120.58 (17)
O1—C3—C8	110.14 (14)	C13—C12—C11	121.33 (19)
O1—C3—C2	109.69 (15)	C13—C12—H12A	119.3
C8—C3—C2	109.78 (15)	C11—C12—H12A	119.3
O1—C3—C4	105.66 (14)	C12—C13—C14	120.12 (19)
C8—C3—C4	112.92 (15)	C12—C13—H13A	119.9
C2—C3—C4	108.54 (14)	C14—C13—H13A	119.9
C9—C4—C5	112.31 (15)	O3—C14—C15	124.8 (2)
C9—C4—C3	112.70 (14)	O3—C14—C13	115.54 (19)
C5—C4—C3	111.46 (14)	C15—C14—C13	119.67 (18)
C9—C4—H4A	106.6	C14—C15—C16	119.4 (2)
C5—C4—H4A	106.6	C14—C15—H15A	120.3
C3—C4—H4A	106.6	C16—C15—H15A	120.3
C6—C5—C11	112.13 (14)	C11—C16—C15	122.11 (18)
C6—C5—C4	108.23 (14)	C11—C16—H16A	118.9
C11—C5—C4	113.58 (14)	C15—C16—H16A	118.9
C6—C5—H5A	107.5	O3—C17—H17A	109.5
C11—C5—H5A	107.5	O3—C17—H17B	109.5
C4—C5—H5A	107.5	H17A—C17—H17B	109.5
C7—C6—C1	105.28 (16)	O3—C17—H17C	109.5
C7—C6—C5	130.39 (16)	H17A—C17—H17C	109.5
C1—C6—C5	124.31 (16)	H17B—C17—H17C	109.5
N1—C7—C6	106.07 (16)	C7—C18—H18A	109.5
N1—C7—C18	121.61 (17)	C7—C18—H18B	109.5
C6—C7—C18	132.32 (17)	H18A—C18—H18B	109.5
C3—C8—H8A	109.5	C7—C18—H18C	109.5
C3—C8—H8B	109.5	H18A—C18—H18C	109.5
H8A—C8—H8B	109.5	H18B—C18—H18C	109.5

C7—N1—N2—C1	−0.1 (2)	N2—N1—C7—C6	0.7 (2)
N1—N2—C1—C6	−0.6 (2)	N2—N1—C7—C18	−178.36 (18)
N1—N2—C1—C2	177.76 (17)	C1—C6—C7—N1	−1.0 (2)
N2—C1—C2—C3	−160.60 (17)	C5—C6—C7—N1	−179.50 (18)
C6—C1—C2—C3	17.5 (2)	C1—C6—C7—C18	178.0 (2)
C1—C2—C3—O1	65.31 (18)	C5—C6—C7—C18	−0.6 (4)
C1—C2—C3—C8	−173.54 (15)	C5—C4—C9—O2	−132.80 (19)
C1—C2—C3—C4	−49.68 (19)	C3—C4—C9—O2	100.3 (2)
O1—C3—C4—C9	78.02 (18)	C5—C4—C9—C10	47.5 (2)
C8—C3—C4—C9	−42.4 (2)	C3—C4—C9—C10	−79.4 (2)
C2—C3—C4—C9	−164.39 (15)	C6—C5—C11—C16	−57.2 (2)
O1—C3—C4—C5	−49.32 (17)	C4—C5—C11—C16	65.9 (2)
C8—C3—C4—C5	−169.78 (15)	C6—C5—C11—C12	117.95 (19)
C2—C3—C4—C5	68.27 (18)	C4—C5—C11—C12	−118.97 (19)
C9—C4—C5—C6	−174.75 (14)	C16—C11—C12—C13	1.4 (3)
C3—C4—C5—C6	−47.19 (18)	C5—C11—C12—C13	−173.94 (19)
C9—C4—C5—C11	60.06 (19)	C11—C12—C13—C14	−0.4 (3)
C3—C4—C5—C11	−172.39 (14)	C17—O3—C14—C15	−3.0 (4)
N2—C1—C6—C7	1.0 (2)	C17—O3—C14—C13	178.2 (2)
C2—C1—C6—C7	−177.33 (17)	C12—C13—C14—O3	178.0 (2)
N2—C1—C6—C5	179.63 (16)	C12—C13—C14—C15	−1.0 (3)
C2—C1—C6—C5	1.3 (3)	O3—C14—C15—C16	−177.5 (2)
C11—C5—C6—C7	−42.2 (3)	C13—C14—C15—C16	1.3 (4)
C4—C5—C6—C7	−168.21 (18)	C12—C11—C16—C15	−1.0 (3)
C11—C5—C6—C1	139.57 (18)	C5—C11—C16—C15	174.3 (2)
C4—C5—C6—C1	13.5 (2)	C14—C15—C16—C11	−0.3 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···N2ⁱ	0.81 (3)	2.15 (3)	2.948 (2)	168 (2)
N1—H1N···N2ⁱⁱ	0.87 (2)	2.27 (2)	3.093 (2)	157 (2)

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₈H₂₂N₂O₃
M_r	314.38
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	18.3693 (14), 5.6971 (4), 16.3049 (12)
β (°)	109.526 (1)
V (Å³)	1608.2 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.974, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	17994, 4015, 2740
R_int	0.053
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.151, 1.00
No. of reflections	4015
No. of parameters	220
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.26

Computer programs: APEX2 (Bruker, 2005), SAINT-Plus (Bruker, 2001), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···N2ⁱ	0.81 (3)	2.15 (3)	2.948 (2)	168 (2)
N1—H1N···N2ⁱⁱ	0.87 (2)	2.27 (2)	3.093 (2)	157 (2)

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1, y+1/2, −z+3/2.

Acknowledgements

We thank Baku State University and Vladimir State University for supporting this study.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2001). SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Pramula, B., Rajanarender, E., Shoolery, J. N. & Krishna, M. (1985). Indian J. Chem. Sect. B, 24, 1255–1258. Google Scholar
Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 69| Part 2| February 2013| Page o243

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

rac-1-[6-Hy­dr­oxy-4-(4-meth­­oxy­phen­yl)-3,6-di­methyl-4,5,6,7-tetra­hydro-2H-indazol-5-yl]ethanone

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

rac-1-[6-Hydroxy-4-(4-methoxyphenyl)-3,6-dimethyl-4,5,6,7-tetrahydro-2H-indazol-5-yl]ethanone