#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/65/2226571.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2226571
loop_
_publ_author_name
'Maharramov, Abel M.'
'Ismiyev, Arif I.'
'Rashidov, Bahruz A.'
'Askerov, Rizvan K.'
'Khrustalev, Victor N.'
_publ_section_title
;
 rac-5-Acetyl-6-hydroxy-3,6-dimethyl-4-phenyl-2H-4,5,6,7-tetrahydroindazol-1-ium
 chloride
;
_journal_coeditor_code           KP2265
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1848
_journal_paper_doi               10.1107/S1600536810024281
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C17 H21 N2 O2 +, Cl -'
_chemical_formula_moiety         'C17 H21 N2 O2 +, Cl -'
_chemical_formula_sum            'C17 H21 Cl N2 O2'
_chemical_formula_weight         320.81
_chemical_name_systematic
;
rac-5-Acetyl-6-hydroxy-3,6-dimethyl-4-phenyl-2H-4,5,6,7-
tetrahydroindazol-1-ium chloride
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                88.1450(10)
_cell_angle_beta                 87.3850(10)
_cell_angle_gamma                67.8820(10)
_cell_formula_units_Z            2
_cell_length_a                   6.9661(3)
_cell_length_b                   8.3527(4)
_cell_length_c                   15.6739(7)
_cell_measurement_reflns_used    4494
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.296
_cell_measurement_theta_min      2.602
_cell_volume                     843.89(7)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2001)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0151
_diffrn_reflns_av_sigmaI/netI    0.0182
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9861
_diffrn_reflns_theta_full        28.39
_diffrn_reflns_theta_max         28.39
_diffrn_reflns_theta_min         2.60
_exptl_absorpt_coefficient_mu    0.235
_exptl_absorpt_correction_T_max  0.9545
_exptl_absorpt_correction_T_min  0.9329
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.228
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         4188
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0434
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0702P)²+0.1788P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1186
_refine_ls_wR_factor_ref         0.1303
_reflns_number_gt                3279
_reflns_number_total             4188
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            kp2265.cif
_cod_data_source_block           I
_cod_database_code               2226571
_cod_database_fobs_code          2226571
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl 0.79637(7) 0.21601(6) 0.42366(3) 0.06850(18) Uani d . 1 . .
O O1 0.82690(19) 0.50419(14) 0.28900(7) 0.0544(3) Uani d . 1 . .
H H1A 0.8256 0.4295 0.3240 0.082 Uiso calc R 1 . .
C C2 0.6910(2) 0.84494(17) 0.21715(8) 0.0370(3) Uani d . 1 . .
H H2A 0.6654 0.7634 0.1801 0.044 Uiso calc R 1 . .
C C7 0.6848(2) 1.00157(18) 0.16319(9) 0.0403(3) Uani d . 1 . .
C C3 0.9075(2) 0.75279(17) 0.25585(9) 0.0407(3) Uani d . 1 . .
H H3A 0.9415 0.8418 0.2835 0.049 Uiso calc R 1 . .
C C1A 0.5285(2) 0.89218(18) 0.28808(9) 0.0408(3) Uani d . 1 . .
O O2 1.2259(2) 0.71271(18) 0.18122(10) 0.0707(4) Uani d . 1 . .
N N2 0.2393(2) 0.9911(2) 0.36527(10) 0.0608(4) Uani d . 1 . .
H H2B 0.1114 1.0441 0.3808 0.073 Uiso calc R 1 . .
C C1 0.3197(2) 0.99656(19) 0.28640(10) 0.0469(3) Uani d . 1 . .
C C13 1.0750(2) 0.67523(19) 0.18596(10) 0.0475(3) Uani d . 1 . .
C C8 0.6566(2) 1.1566(2) 0.20107(11) 0.0484(3) Uani d . 1 . .
H H8A 0.6442 1.1642 0.2603 0.058 Uiso calc R 1 . .
C C5A 0.5664(3) 0.8269(2) 0.37032(9) 0.0497(4) Uani d . 1 . .
N N1 0.3884(3) 0.8905(2) 0.41623(9) 0.0626(4) Uani d . 1 . .
H H1B 0.3722 0.8703 0.4697 0.075 Uiso calc R 1 . .
C C6 0.1911(2) 1.0995(2) 0.21689(12) 0.0557(4) Uani d . 1 . .
H H6A 0.0508 1.1562 0.2381 0.084 Uiso calc R 1 . .
H H6B 0.1942 1.0247 0.1712 0.084 Uiso calc R 1 . .
H H6C 0.2445 1.1845 0.1962 0.084 Uiso calc R 1 . .
C C4 0.9097(3) 0.6160(2) 0.32611(9) 0.0483(3) Uani d . 1 . .
C C12 0.7041(3) 0.9940(3) 0.07526(11) 0.0643(5) Uani d . 1 . .
H H12A 0.7216 0.8916 0.0483 0.077 Uiso calc R 1 . .
C C9 0.6467(3) 1.3007(2) 0.15225(14) 0.0623(5) Uani d . 1 . .
H H9A 0.6254 1.4045 0.1787 0.075 Uiso calc R 1 . .
C C14 1.0503(3) 0.5535(2) 0.12344(12) 0.0611(4) Uani d . 1 . .
H H14A 1.1675 0.5174 0.0839 0.092 Uiso calc R 1 . .
H H14B 0.9259 0.6107 0.0928 0.092 Uiso calc R 1 . .
H H14C 1.0416 0.4543 0.1535 0.092 Uiso calc R 1 . .
C C5 0.7689(3) 0.7091(2) 0.40209(10) 0.0577(4) Uani d . 1 . .
H H5A 0.7487 0.6250 0.4419 0.069 Uiso calc R 1 . .
H H5B 0.8335 0.7746 0.4318 0.069 Uiso calc R 1 . .
C C15 1.1284(3) 0.5161(3) 0.35650(13) 0.0697(5) Uani d . 1 . .
H H15A 1.1245 0.4336 0.3999 0.104 Uiso calc R 1 . .
H H15B 1.1824 0.5952 0.3795 0.104 Uiso calc R 1 . .
H H15C 1.2160 0.4568 0.3092 0.104 Uiso calc R 1 . .
C C11 0.6976(4) 1.1385(3) 0.02648(13) 0.0857(7) Uani d . 1 . .
H H11A 0.7135 1.1313 -0.0327 0.103 Uiso calc R 1 . .
C C10 0.6680(3) 1.2903(3) 0.06526(15) 0.0771(6) Uani d . 1 . .
H H10A 0.6624 1.3867 0.0325 0.092 Uiso calc R 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C4 O1 H1A . . 109.5 ?
C1A C2 C7 . . 112.15(11) ?
C1A C2 C3 . . 109.00(11) ?
C7 C2 C3 . . 110.88(11) ?
C1A C2 H2A . . 108.2 ?
C7 C2 H2A . . 108.2 ?
C3 C2 H2A . . 108.2 ?
C12 C7 C8 . . 118.09(14) ?
C12 C7 C2 . . 121.10(14) ?
C8 C7 C2 . . 120.80(12) ?
C13 C3 C2 . . 111.19(11) ?
C13 C3 C4 . . 111.65(11) ?
C2 C3 C4 . . 112.95(12) ?
C13 C3 H3A . . 106.9 ?
C2 C3 H3A . . 106.9 ?
C4 C3 H3A . . 106.9 ?
C5A C1A C1 . . 106.91(13) ?
C5A C1A C2 . . 123.23(14) ?
C1 C1A C2 . . 129.81(13) ?
C1 N2 N1 . . 109.73(14) ?
C1 N2 H2B . . 125.1 ?
N1 N2 H2B . . 125.1 ?
N2 C1 C1A . . 106.79(14) ?
N2 C1 C6 . . 121.61(14) ?
C1A C1 C6 . . 131.60(13) ?
O2 C13 C14 . . 120.14(15) ?
O2 C13 C3 . . 120.00(15) ?
C14 C13 C3 . . 119.86(14) ?
C7 C8 C9 . . 121.12(16) ?
C7 C8 H8A . . 119.4 ?
C9 C8 H8A . . 119.4 ?
N1 C5A C1A . . 107.79(15) ?
N1 C5A C5 . . 126.19(14) ?
C1A C5A C5 . . 126.01(14) ?
C5A N1 N2 . . 108.77(13) ?
C5A N1 H1B . . 125.6 ?
N2 N1 H1B . . 125.6 ?
C1 C6 H6A . . 109.5 ?
C1 C6 H6B . . 109.5 ?
H6A C6 H6B . . 109.5 ?
C1 C6 H6C . . 109.5 ?
H6A C6 H6C . . 109.5 ?
H6B C6 H6C . . 109.5 ?
O1 C4 C15 . . 111.19(14) ?
O1 C4 C5 . . 109.66(14) ?
C15 C4 C5 . . 109.42(14) ?
O1 C4 C3 . . 106.27(11) ?
C15 C4 C3 . . 111.47(14) ?
C5 C4 C3 . . 108.75(12) ?
C7 C12 C11 . . 120.6(2) ?
C7 C12 H12A . . 119.7 ?
C11 C12 H12A . . 119.7 ?
C10 C9 C8 . . 119.94(19) ?
C10 C9 H9A . . 120.0 ?
C8 C9 H9A . . 120.0 ?
C13 C14 H14A . . 109.5 ?
C13 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C13 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C5A C5 C4 . . 109.23(12) ?
C5A C5 H5A . . 109.8 ?
C4 C5 H5A . . 109.8 ?
C5A C5 H5B . . 109.8 ?
C4 C5 H5B . . 109.8 ?
H5A C5 H5B . . 108.3 ?
C4 C15 H15A . . 109.5 ?
C4 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C4 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C10 C11 C12 . . 120.22(19) ?
C10 C11 H11A . . 119.9 ?
C12 C11 H11A . . 119.9 ?
C11 C10 C9 . . 120.03(17) ?
C11 C10 H10A . . 120.0 ?
C9 C10 H10A . . 120.0 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C4 . 1.419(2) ?
O1 H1A . 0.8200 ?
C2 C1A . 1.5001(18) ?
C2 C7 . 1.5224(18) ?
C2 C3 . 1.5535(19) ?
C2 H2A . 0.9800 ?
C7 C12 . 1.380(2) ?
C7 C8 . 1.384(2) ?
C3 C13 . 1.530(2) ?
C3 C4 . 1.5573(19) ?
C3 H3A . 0.9800 ?
C1A C5A . 1.380(2) ?
C1A C1 . 1.387(2) ?
O2 C13 . 1.203(2) ?
N2 C1 . 1.3404(19) ?
N2 N1 . 1.341(2) ?
N2 H2B . 0.8600 ?
C1 C6 . 1.476(2) ?
C13 C14 . 1.495(2) ?
C8 C9 . 1.386(2) ?
C8 H8A . 0.9300 ?
C5A N1 . 1.336(2) ?
C5A C5 . 1.481(3) ?
N1 H1B . 0.8600 ?
C6 H6A . 0.9600 ?
C6 H6B . 0.9600 ?
C6 H6C . 0.9600 ?
C4 C15 . 1.526(2) ?
C4 C5 . 1.537(2) ?
C12 C11 . 1.395(3) ?
C12 H12A . 0.9300 ?
C9 C10 . 1.367(3) ?
C9 H9A . 0.9300 ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
C11 C10 . 1.364(4) ?
C11 H11A . 0.9300 ?
C10 H10A . 0.9300 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1 H1A Cl 8_655 0.82 2.39 3.2110(14) 176 yes
N2 H2B Cl 8_655 0.86 2.21 3.0620(14) 171 yes
N1 H1B Cl 5_665 0.86 2.25 3.0280(15) 150 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C1A C2 C7 C12 . . . . -137.04(15) ?
C3 C2 C7 C12 . . . . 100.85(16) ?
C1A C2 C7 C8 . . . . 42.07(18) ?
C3 C2 C7 C8 . . . . -80.04(15) ?
C1A C2 C3 C13 . . . . 170.59(11) ?
C7 C2 C3 C13 . . . . -65.48(14) ?
C1A C2 C3 C4 . . . . 44.16(15) ?
C7 C2 C3 C4 . . . . 168.09(11) ?
C7 C2 C1A C5A . . . . -136.73(14) ?
C3 C2 C1A C5A . . . . -13.55(19) ?
C7 C2 C1A C1 . . . . 46.4(2) ?
C3 C2 C1A C1 . . . . 169.55(14) ?
N1 N2 C1 C1A . . . . 0.90(18) ?
N1 N2 C1 C6 . . . . -179.36(15) ?
C5A C1A C1 N2 . . . . -0.21(17) ?
C2 C1A C1 N2 . . . . 177.07(14) ?
C5A C1A C1 C6 . . . . -179.92(16) ?
C2 C1A C1 C6 . . . . -2.6(3) ?
C2 C3 C13 O2 . . . . 125.03(16) ?
C4 C3 C13 O2 . . . . -107.83(16) ?
C2 C3 C13 C14 . . . . -54.72(17) ?
C4 C3 C13 C14 . . . . 72.43(18) ?
C12 C7 C8 C9 . . . . 0.4(2) ?
C2 C7 C8 C9 . . . . -178.70(14) ?
C1 C1A C5A N1 . . . . -0.54(17) ?
C2 C1A C5A N1 . . . . -178.05(13) ?
C1 C1A C5A C5 . . . . -179.78(15) ?
C2 C1A C5A C5 . . . . 2.7(2) ?
C1A C5A N1 N2 . . . . 1.10(19) ?
C5 C5A N1 N2 . . . . -179.66(16) ?
C1 N2 N1 C5A . . . . -1.26(19) ?
C13 C3 C4 O1 . . . . -72.98(16) ?
C2 C3 C4 O1 . . . . 53.21(15) ?
C13 C3 C4 C15 . . . . 48.32(18) ?
C2 C3 C4 C15 . . . . 174.51(13) ?
C13 C3 C4 C5 . . . . 169.05(13) ?
C2 C3 C4 C5 . . . . -64.77(16) ?
C8 C7 C12 C11 . . . . 0.7(3) ?
C2 C7 C12 C11 . . . . 179.84(18) ?
C7 C8 C9 C10 . . . . -1.0(2) ?
N1 C5A C5 C4 . . . . 159.56(16) ?
C1A C5A C5 C4 . . . . -21.3(2) ?
O1 C4 C5 C5A . . . . -66.44(16) ?
C15 C4 C5 C5A . . . . 171.35(15) ?
C3 C4 C5 C5A . . . . 49.37(18) ?
C7 C12 C11 C10 . . . . -1.3(3) ?
C12 C11 C10 C9 . . . . 0.7(4) ?
C8 C9 C10 C11 . . . . 0.5(3) ?
