rac-5-Acetyl-6-hy­droxy-3,6-dimethyl-4-phenyl-2H-4,5,6,7-tetra­hydro­indazol-1-ium chloride

Maharramov, A.M.; Ismiyev, A.I.; Rashidov, B.A.; Askerov, R.K.; Khrustalev, V.N.

doi:10.1107/S1600536810024281

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1848

doi:10.1107/S1600536810024281

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rac-5-Acetyl-6-hydroxy-3,6-dimethyl-4-phenyl-2H-4,5,6,7-tetrahydroindazol-1-ium chloride

Abel M. Maharramov,^a Arif I. Ismiyev,^a Bahruz A. Rashidov,^a ^* Rizvan K. Askerov ^a and Victor N. Khrustalev ^b

^aBaku State University, Z. Khalilov St. 23, Baku, AZ-1148, Azerbaijan, and ^bX-Ray Structural Centre, A.N.Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov St., B-334, Moscow 119991, Russian Federation
^*Correspondence e-mail: Bahruz_81@mail.ru

(Received 10 June 2010; accepted 22 June 2010; online 26 June 2010)

The structure of the title compound, C₁₇H₂₁N₂O₂⁺·Cl⁻, is of interest with respect to its biological activity. The title compound comprises an organic cation and a chloride anion in the asymmetric unit. The positive charge is localized in a pyrazole moiety forming a pyrazolium cation. The structure displays intermolecular O—H⋯Cl and N—H⋯Cl hydrogen bonding.

Related literature

For general background, see: Raptis et al. (1993 ); Rabe (1904 ).

Experimental

Crystal data

C₁₇H₂₁N₂O₂⁺·Cl⁻
M_r = 320.81
Triclinic, $[P \overline 1]$
a = 6.9661 (3) Å
b = 8.3527 (4) Å
c = 15.6739 (7) Å
α = 88.145 (1)°
β = 87.385 (1)°
γ = 67.882 (1)°
V = 843.89 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 296 K
0.30 × 0.30 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.933, T_max = 0.955
9861 measured reflections
4188 independent reflections
3279 reflections with I > 2σ(I)
R_int = 0.015

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.130
S = 1.00
4188 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯Cl	0.82	2.39	3.2110 (14)	176
N2—H2B⋯Cl	0.86	2.21	3.0620 (14)	171
N1—H1B⋯Cl	0.86	2.25	3.0280 (15)	150

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/S1600536810024281/kp2265sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810024281/kp2265Isup2.hkl

checkCIF report

Comment top

(rac)-5-Acetyl-6-hydroxy-3,6-dimethyl-4-phenyl-2H-4,5,6,7- tetrahyroindazolium chloride (I) have good antibacterial and biological properties. We have synthesised the title compound, (I), and its structure is reported here (Fig. 1). The two [(C2(R),C4(R)] of three stereogenic centres of tetrahydroindazole moiety are of the same chirality. As the crystal crystallises in the centrosymmetric space group, the racemate (1:1) is present. The crystal structure involves O—H···Cl, and N—H···C intermolecular hydrogen bonds (Table 1 and Fig. 2).

Related literature top

For general background [to what?], see: Raptis et al. (1993); Rabe (1904).

Experimental top

2,4-Diacetyl-5-hydroxy-5-methyl-3-phenylcyclohexanon (20 mmol)and hydrazine hydrate (20 mmol) were dissolved in 20 ml ethanol. The mixture was stirred at 340 K within 10 h. Through suspension in absolute toluene a flow of dry gaseous hydrogen chloride was used at 278-283 K. From a solution a white solid was obtained. A crude product was filtered and washed with ethanol. Then, the crude product was dissolved in ethanol (50 ml) and recrystallised to yield colourless block-shaped crystals of (I).

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. Displacement ellipsoids were drawn at the 30% probability level.
	Fig. 2. A hydrogen-bonded (dashed lines) ribbon in the title compound. H atoms not involved in hydrogen bonding have been omitted for clarity.

rac-5-Acetyl-6-hydroxy-3,6-dimethyl-4-phenyl-2H-4,5,6,7- tetrahydroindazol-1-ium chloride top

Crystal data top

C₁₇H₂₁N₂O₂⁺·Cl⁻	Z = 2
M_r = 320.81	F(000) = 340
Triclinic, P1	D_x = 1.263 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.9661 (3) Å	Cell parameters from 4494 reflections
b = 8.3527 (4) Å	θ = 2.6–28.3°
c = 15.6739 (7) Å	µ = 0.24 mm⁻¹
α = 88.145 (1)°	T = 296 K
β = 87.385 (1)°	Prism, colourless
γ = 67.882 (1)°	0.30 × 0.30 × 0.20 mm
V = 843.89 (7) Å³

Data collection top

Bruker APEXII CCD diffractometer	4188 independent reflections
Radiation source: fine-focus sealed tube	3279 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.015
ϕ and ω scans	θ_max = 28.4°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −9→9
T_min = 0.933, T_max = 0.955	k = −11→11
9861 measured reflections	l = −20→20

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)] = 0.043	Hydrogen site location: difference Fourier map
wR(F²) = 0.130	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0702P)² + 0.1788P] where P = (F_o² + 2F_c²)/3
4188 reflections	(Δ/σ)_max < 0.001
199 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₇H₂₁N₂O₂⁺·Cl⁻	γ = 67.882 (1)°
M_r = 320.81	V = 843.89 (7) Å³
Triclinic, P1	Z = 2
a = 6.9661 (3) Å	Mo Kα radiation
b = 8.3527 (4) Å	µ = 0.24 mm⁻¹
c = 15.6739 (7) Å	T = 296 K
α = 88.145 (1)°	0.30 × 0.30 × 0.20 mm
β = 87.385 (1)°

Data collection top

Bruker APEXII CCD diffractometer	4188 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	3279 reflections with I > 2σ(I)
T_min = 0.933, T_max = 0.955	R_int = 0.015
9861 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.130	H-atom parameters constrained
S = 1.00	Δρ_max = 0.31 e Å⁻³
4188 reflections	Δρ_min = −0.23 e Å⁻³
199 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
Cl	0.79637 (7)	0.21601 (6)	0.42366 (3)	0.06850 (18)
O1	0.82690 (19)	0.50419 (14)	0.28900 (7)	0.0544 (3)
H1A	0.8256	0.4295	0.3240	0.082*
C2	0.6910 (2)	0.84494 (17)	0.21715 (8)	0.0370 (3)
H2A	0.6654	0.7634	0.1801	0.044*
C7	0.6848 (2)	1.00157 (18)	0.16319 (9)	0.0403 (3)
C3	0.9075 (2)	0.75279 (17)	0.25585 (9)	0.0407 (3)
H3A	0.9415	0.8418	0.2835	0.049*
C1A	0.5285 (2)	0.89218 (18)	0.28808 (9)	0.0408 (3)
O2	1.2259 (2)	0.71271 (18)	0.18122 (10)	0.0707 (4)
N2	0.2393 (2)	0.9911 (2)	0.36527 (10)	0.0608 (4)
H2B	0.1114	1.0441	0.3808	0.073*
C1	0.3197 (2)	0.99656 (19)	0.28640 (10)	0.0469 (3)
C13	1.0750 (2)	0.67523 (19)	0.18596 (10)	0.0475 (3)
C8	0.6566 (2)	1.1566 (2)	0.20107 (11)	0.0484 (3)
H8A	0.6442	1.1642	0.2603	0.058*
C5A	0.5664 (3)	0.8269 (2)	0.37032 (9)	0.0497 (4)
N1	0.3884 (3)	0.8905 (2)	0.41623 (9)	0.0626 (4)
H1B	0.3722	0.8703	0.4697	0.075*
C6	0.1911 (2)	1.0995 (2)	0.21689 (12)	0.0557 (4)
H6A	0.0508	1.1562	0.2381	0.084*
H6B	0.1942	1.0247	0.1712	0.084*
H6C	0.2445	1.1845	0.1962	0.084*
C4	0.9097 (3)	0.6160 (2)	0.32611 (9)	0.0483 (3)
C12	0.7041 (3)	0.9940 (3)	0.07526 (11)	0.0643 (5)
H12A	0.7216	0.8916	0.0483	0.077*
C9	0.6467 (3)	1.3007 (2)	0.15225 (14)	0.0623 (5)
H9A	0.6254	1.4045	0.1787	0.075*
C14	1.0503 (3)	0.5535 (2)	0.12344 (12)	0.0611 (4)
H14A	1.1675	0.5174	0.0839	0.092*
H14B	0.9259	0.6107	0.0928	0.092*
H14C	1.0416	0.4543	0.1535	0.092*
C5	0.7689 (3)	0.7091 (2)	0.40209 (10)	0.0577 (4)
H5A	0.7487	0.6250	0.4419	0.069*
H5B	0.8335	0.7746	0.4318	0.069*
C15	1.1284 (3)	0.5161 (3)	0.35650 (13)	0.0697 (5)
H15A	1.1245	0.4336	0.3999	0.104*
H15B	1.1824	0.5952	0.3795	0.104*
H15C	1.2160	0.4568	0.3092	0.104*
C11	0.6976 (4)	1.1385 (3)	0.02648 (13)	0.0857 (7)
H11A	0.7135	1.1313	−0.0327	0.103*
C10	0.6680 (3)	1.2903 (3)	0.06526 (15)	0.0771 (6)
H10A	0.6624	1.3867	0.0325	0.092*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl	0.0681 (3)	0.0699 (3)	0.0529 (2)	−0.0135 (2)	0.0232 (2)	0.0174 (2)
O1	0.0784 (8)	0.0446 (6)	0.0443 (6)	−0.0286 (6)	−0.0005 (5)	0.0089 (4)
C2	0.0406 (7)	0.0392 (6)	0.0305 (6)	−0.0150 (5)	0.0049 (5)	0.0008 (5)
C7	0.0331 (6)	0.0466 (7)	0.0376 (6)	−0.0120 (5)	0.0024 (5)	0.0094 (5)
C3	0.0458 (7)	0.0372 (6)	0.0379 (6)	−0.0148 (6)	0.0001 (5)	0.0027 (5)
C1A	0.0477 (7)	0.0400 (7)	0.0371 (6)	−0.0202 (6)	0.0090 (5)	−0.0008 (5)
O2	0.0494 (7)	0.0660 (8)	0.0957 (10)	−0.0224 (6)	0.0128 (6)	0.0015 (7)
N2	0.0598 (8)	0.0617 (8)	0.0610 (8)	−0.0257 (7)	0.0290 (7)	−0.0075 (7)
C1	0.0488 (8)	0.0423 (7)	0.0520 (8)	−0.0216 (6)	0.0165 (6)	−0.0059 (6)
C13	0.0442 (7)	0.0380 (7)	0.0539 (8)	−0.0096 (6)	0.0047 (6)	0.0090 (6)
C8	0.0455 (8)	0.0493 (8)	0.0530 (8)	−0.0212 (6)	−0.0043 (6)	0.0093 (6)
C5A	0.0667 (10)	0.0497 (8)	0.0354 (7)	−0.0265 (7)	0.0129 (6)	−0.0014 (6)
N1	0.0789 (10)	0.0658 (9)	0.0437 (7)	−0.0307 (8)	0.0246 (7)	−0.0027 (6)
C6	0.0420 (8)	0.0487 (8)	0.0718 (11)	−0.0128 (7)	0.0071 (7)	0.0005 (7)
C4	0.0620 (9)	0.0437 (7)	0.0372 (7)	−0.0179 (7)	−0.0044 (6)	0.0075 (6)
C12	0.0766 (12)	0.0636 (10)	0.0398 (8)	−0.0138 (9)	0.0079 (8)	0.0095 (7)
C9	0.0492 (9)	0.0508 (9)	0.0895 (13)	−0.0225 (7)	−0.0095 (8)	0.0199 (9)
C14	0.0675 (11)	0.0518 (9)	0.0554 (9)	−0.0145 (8)	0.0176 (8)	−0.0058 (7)
C5	0.0796 (11)	0.0598 (10)	0.0326 (7)	−0.0256 (9)	0.0001 (7)	0.0065 (6)
C15	0.0735 (12)	0.0644 (11)	0.0615 (11)	−0.0147 (9)	−0.0182 (9)	0.0181 (9)
C11	0.0979 (16)	0.0927 (16)	0.0494 (10)	−0.0205 (13)	0.0106 (10)	0.0316 (11)
C10	0.0620 (11)	0.0730 (13)	0.0880 (14)	−0.0198 (10)	−0.0012 (10)	0.0454 (12)

Geometric parameters (Å, º) top

O1—C4	1.419 (2)	C5A—C5	1.481 (3)
O1—H1A	0.8200	N1—H1B	0.8600
C2—C1A	1.5001 (18)	C6—H6A	0.9600
C2—C7	1.5224 (18)	C6—H6B	0.9600
C2—C3	1.5535 (19)	C6—H6C	0.9600
C2—H2A	0.9800	C4—C15	1.526 (2)
C7—C12	1.380 (2)	C4—C5	1.537 (2)
C7—C8	1.384 (2)	C12—C11	1.395 (3)
C3—C13	1.530 (2)	C12—H12A	0.9300
C3—C4	1.5573 (19)	C9—C10	1.367 (3)
C3—H3A	0.9800	C9—H9A	0.9300
C1A—C5A	1.380 (2)	C14—H14A	0.9600
C1A—C1	1.387 (2)	C14—H14B	0.9600
O2—C13	1.203 (2)	C14—H14C	0.9600
N2—C1	1.3404 (19)	C5—H5A	0.9700
N2—N1	1.341 (2)	C5—H5B	0.9700
N2—H2B	0.8600	C15—H15A	0.9600
C1—C6	1.476 (2)	C15—H15B	0.9600
C13—C14	1.495 (2)	C15—H15C	0.9600
C8—C9	1.386 (2)	C11—C10	1.364 (4)
C8—H8A	0.9300	C11—H11A	0.9300
C5A—N1	1.336 (2)	C10—H10A	0.9300

C4—O1—H1A	109.5	C1—C6—H6C	109.5
C1A—C2—C7	112.15 (11)	H6A—C6—H6C	109.5
C1A—C2—C3	109.00 (11)	H6B—C6—H6C	109.5
C7—C2—C3	110.88 (11)	O1—C4—C15	111.19 (14)
C1A—C2—H2A	108.2	O1—C4—C5	109.66 (14)
C7—C2—H2A	108.2	C15—C4—C5	109.42 (14)
C3—C2—H2A	108.2	O1—C4—C3	106.27 (11)
C12—C7—C8	118.09 (14)	C15—C4—C3	111.47 (14)
C12—C7—C2	121.10 (14)	C5—C4—C3	108.75 (12)
C8—C7—C2	120.80 (12)	C7—C12—C11	120.6 (2)
C13—C3—C2	111.19 (11)	C7—C12—H12A	119.7
C13—C3—C4	111.65 (11)	C11—C12—H12A	119.7
C2—C3—C4	112.95 (12)	C10—C9—C8	119.94 (19)
C13—C3—H3A	106.9	C10—C9—H9A	120.0
C2—C3—H3A	106.9	C8—C9—H9A	120.0
C4—C3—H3A	106.9	C13—C14—H14A	109.5
C5A—C1A—C1	106.91 (13)	C13—C14—H14B	109.5
C5A—C1A—C2	123.23 (14)	H14A—C14—H14B	109.5
C1—C1A—C2	129.81 (13)	C13—C14—H14C	109.5
C1—N2—N1	109.73 (14)	H14A—C14—H14C	109.5
C1—N2—H2B	125.1	H14B—C14—H14C	109.5
N1—N2—H2B	125.1	C5A—C5—C4	109.23 (12)
N2—C1—C1A	106.79 (14)	C5A—C5—H5A	109.8
N2—C1—C6	121.61 (14)	C4—C5—H5A	109.8
C1A—C1—C6	131.60 (13)	C5A—C5—H5B	109.8
O2—C13—C14	120.14 (15)	C4—C5—H5B	109.8
O2—C13—C3	120.00 (15)	H5A—C5—H5B	108.3
C14—C13—C3	119.86 (14)	C4—C15—H15A	109.5
C7—C8—C9	121.12 (16)	C4—C15—H15B	109.5
C7—C8—H8A	119.4	H15A—C15—H15B	109.5
C9—C8—H8A	119.4	C4—C15—H15C	109.5
N1—C5A—C1A	107.79 (15)	H15A—C15—H15C	109.5
N1—C5A—C5	126.19 (14)	H15B—C15—H15C	109.5
C1A—C5A—C5	126.01 (14)	C10—C11—C12	120.22 (19)
C5A—N1—N2	108.77 (13)	C10—C11—H11A	119.9
C5A—N1—H1B	125.6	C12—C11—H11A	119.9
N2—N1—H1B	125.6	C11—C10—C9	120.03 (17)
C1—C6—H6A	109.5	C11—C10—H10A	120.0
C1—C6—H6B	109.5	C9—C10—H10A	120.0
H6A—C6—H6B	109.5

C1A—C2—C7—C12	−137.04 (15)	C1—C1A—C5A—N1	−0.54 (17)
C3—C2—C7—C12	100.85 (16)	C2—C1A—C5A—N1	−178.05 (13)
C1A—C2—C7—C8	42.07 (18)	C1—C1A—C5A—C5	−179.78 (15)
C3—C2—C7—C8	−80.04 (15)	C2—C1A—C5A—C5	2.7 (2)
C1A—C2—C3—C13	170.59 (11)	C1A—C5A—N1—N2	1.10 (19)
C7—C2—C3—C13	−65.48 (14)	C5—C5A—N1—N2	−179.66 (16)
C1A—C2—C3—C4	44.16 (15)	C1—N2—N1—C5A	−1.26 (19)
C7—C2—C3—C4	168.09 (11)	C13—C3—C4—O1	−72.98 (16)
C7—C2—C1A—C5A	−136.73 (14)	C2—C3—C4—O1	53.21 (15)
C3—C2—C1A—C5A	−13.55 (19)	C13—C3—C4—C15	48.32 (18)
C7—C2—C1A—C1	46.4 (2)	C2—C3—C4—C15	174.51 (13)
C3—C2—C1A—C1	169.55 (14)	C13—C3—C4—C5	169.05 (13)
N1—N2—C1—C1A	0.90 (18)	C2—C3—C4—C5	−64.77 (16)
N1—N2—C1—C6	−179.36 (15)	C8—C7—C12—C11	0.7 (3)
C5A—C1A—C1—N2	−0.21 (17)	C2—C7—C12—C11	179.84 (18)
C2—C1A—C1—N2	177.07 (14)	C7—C8—C9—C10	−1.0 (2)
C5A—C1A—C1—C6	−179.92 (16)	N1—C5A—C5—C4	159.56 (16)
C2—C1A—C1—C6	−2.6 (3)	C1A—C5A—C5—C4	−21.3 (2)
C2—C3—C13—O2	125.03 (16)	O1—C4—C5—C5A	−66.44 (16)
C4—C3—C13—O2	−107.83 (16)	C15—C4—C5—C5A	171.35 (15)
C2—C3—C13—C14	−54.72 (17)	C3—C4—C5—C5A	49.37 (18)
C4—C3—C13—C14	72.43 (18)	C7—C12—C11—C10	−1.3 (3)
C12—C7—C8—C9	0.4 (2)	C12—C11—C10—C9	0.7 (4)
C2—C7—C8—C9	−178.70 (14)	C8—C9—C10—C11	0.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···Cl	0.82	2.39	3.2110 (14)	176
N2—H2B···Cl	0.86	2.21	3.0620 (14)	171
N1—H1B···Cl	0.86	2.25	3.0280 (15)	150

Experimental details

Crystal data
Chemical formula	C₁₇H₂₁N₂O₂⁺·Cl⁻
M_r	320.81
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	6.9661 (3), 8.3527 (4), 15.6739 (7)
α, β, γ (°)	88.145 (1), 87.385 (1), 67.882 (1)
V (Å³)	843.89 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.30 × 0.30 × 0.20

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.933, 0.955
No. of measured, independent and observed [I > 2σ(I)] reflections	9861, 4188, 3279
R_int	0.015
(sin θ/λ)_max (Å⁻¹)	0.669

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.130, 1.00
No. of reflections	4188
No. of parameters	199
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.23

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—H1A···Cl	0.82	2.39	3.2110 (14)	176
N2—H2B···Cl	0.86	2.21	3.0620 (14)	171
N1—H1B···Cl	0.86	2.25	3.0280 (15)	150

Acknowledgements

We thank Professor Abel M. Maharramov for fruitful discussions and help with this work.

References

Bruker (2001). SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Rabe, P. (1904). Lieb. Ann. Bd. 332, 18–22. Google Scholar
Raptis, R. G., Staples, R. J., King, C. & Fackler, J. P. (1993). Acta Cryst. C49, 1716–1719. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Sheldrick, G. M. (2003). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. 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 66| Part 7| July 2010| Page o1848

doi:10.1107/S1600536810024281

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

rac-5-Acetyl-6-hy­dr­oxy-3,6-di­methyl-4-phenyl-2H-4,5,6,7-tetra­hydro­indazol-1-ium chloride

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

rac-5-Acetyl-6-hydroxy-3,6-dimethyl-4-phenyl-2H-4,5,6,7-tetrahydroindazol-1-ium chloride