#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/91/2229193.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_2229193
loop_
_publ_author_name
'Maharramov, Abel M.'
'Ismiyev, Arif I.'
'Rashidov, Bahruz A.'
_publ_section_title
;
 Ethyl
 3,6-dihydroxy-6-methyl-4-phenyl-4,5,6,7-tetrahydro-1H-indazole-5-carboxylate
 monohydrate
;
_journal_coeditor_code           PV2374
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o480
_journal_paper_doi               10.1107/S160053681100242X
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C17 H20 N2 O4, H2 O'
_chemical_formula_moiety         'C17 H20 N2 O4, H2 O'
_chemical_formula_sum            'C17 H22 N2 O5'
_chemical_formula_weight         334.37
_chemical_name_systematic
;
Ethyl 3,6-dihydroxy-6-methyl-4-phenyl-4,5,6,7-tetrahydro-1H-indazole-5-
carboxylate monohydrate
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                99.363(6)
_cell_angle_beta                 95.281(6)
_cell_angle_gamma                112.271(4)
_cell_formula_units_Z            2
_cell_length_a                   6.9964(15)
_cell_length_b                   8.8647(19)
_cell_length_c                   15.124(4)
_cell_measurement_reflns_used    909
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      30.58
_cell_measurement_theta_min      2.54
_cell_volume                     844.2(3)
_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  'SHELXL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω'
_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  0.0652
_diffrn_reflns_av_sigmaI/netI    0.1183
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6332
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.54
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.9808
_exptl_absorpt_correction_T_min  0.9808
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.369
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         2889
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0870
_refine_ls_R_factor_gt           0.0768
_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)+(0.0611P)²+0.4352P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1863
_refine_ls_wR_factor_ref         0.1980
_reflns_number_gt                2327
_reflns_number_total             2889
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pv2374.cif
_cod_data_source_block           I
_cod_database_code               2229193
_cod_database_fobs_code          2229193
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
O O1 0.9685(3) 1.3998(2) 0.37394(14) 0.0463(5) Uani d . 1 . .
H H1B 0.9998 1.4897 0.4089 0.069 Uiso calc R 1 . .
O O2 0.7109(3) 0.6179(2) 0.15151(15) 0.0544(6) Uani d . 1 . .
O O3 0.4935(3) 0.7477(2) 0.14842(13) 0.0421(5) Uani d . 1 . .
O O4 0.3968(2) 0.8009(2) 0.33029(13) 0.0363(5) Uani d . 1 . .
H H4A 0.3737 0.7989 0.2759 0.054 Uiso calc R 1 . .
O O5 0.0528(4) 0.5446(3) 0.2177(2) 0.0637(7) Uani d . 1 . .
H H5B 0.009(6) 0.485(6) 0.264(3) 0.081(13) Uiso d . 1 . .
H H5C -0.051(6) 0.563(5) 0.198(3) 0.068(11) Uiso d . 1 . .
N N1 0.8141(3) 1.1503(2) 0.52847(16) 0.0340(5) Uani d . 1 . .
N N2 0.8884(3) 1.3042(2) 0.50553(16) 0.0373(6) Uani d . 1 . .
C C3 0.8995(4) 1.2791(3) 0.41766(18) 0.0326(6) Uani d . 1 . .
C C3A 0.8266(3) 1.1038(3) 0.38069(17) 0.0302(6) Uani d . 1 . .
C C4 0.7975(3) 1.0105(3) 0.28485(17) 0.0306(6) Uani d . 1 . .
H H4B 0.6826 1.0230 0.2490 0.037 Uiso calc R 1 . .
C C5 0.7311(3) 0.8213(3) 0.28392(18) 0.0312(6) Uani d . 1 . .
H H5A 0.8575 0.8062 0.3058 0.037 Uiso calc R 1 . .
C C6 0.5710(3) 0.7581(3) 0.34881(18) 0.0316(6) Uani d . 1 . .
C C7 0.6747(4) 0.8481(3) 0.44704(18) 0.0325(6) Uani d . 1 . .
H H7A 0.5710 0.8228 0.4869 0.039 Uiso calc R 1 . .
H H7B 0.7819 0.8107 0.4667 0.039 Uiso calc R 1 . .
C C7A 0.7705(3) 1.0317(3) 0.45193(17) 0.0307(6) Uani d . 1 . .
C C8 0.9887(4) 1.0726(3) 0.23964(18) 0.0327(6) Uani d . 1 . .
C C9 1.1870(4) 1.1056(3) 0.2856(2) 0.0430(7) Uani d . 1 . .
H H9A 1.2015 1.0902 0.3449 0.052 Uiso calc R 1 . .
C C10 1.3610(5) 1.1603(3) 0.2451(3) 0.0546(9) Uani d . 1 . .
H H10A 1.4921 1.1823 0.2771 0.066 Uiso calc R 1 . .
C C11 1.3422(5) 1.1827(4) 0.1572(3) 0.0635(10) Uani d . 1 . .
H H11A 1.4600 1.2185 0.1294 0.076 Uiso calc R 1 . .
C C12 1.1468(6) 1.1516(4) 0.1104(3) 0.0690(10) Uani d . 1 . .
H H12A 1.1332 1.1688 0.0515 0.083 Uiso calc R 1 . .
C C13 0.9724(5) 1.0950(4) 0.1516(2) 0.0519(8) Uani d . 1 . .
H H13A 0.8412 1.0715 0.1193 0.062 Uiso calc R 1 . .
C C14 0.6486(4) 0.7183(3) 0.18762(19) 0.0350(6) Uani d . 1 . .
C C15 0.3862(5) 0.6480(4) 0.0578(2) 0.0511(8) Uani d . 1 . .
H H15A 0.3097 0.5325 0.0606 0.061 Uiso calc R 1 . .
H H15B 0.4869 0.6527 0.0172 0.061 Uiso calc R 1 . .
C C16 0.2398(6) 0.7190(5) 0.0244(3) 0.0693(10) Uani d . 1 . .
H H16A 0.1663 0.6560 -0.0352 0.104 Uiso calc R 1 . .
H H16B 0.3173 0.8331 0.0217 0.104 Uiso calc R 1 . .
H H16C 0.1409 0.7137 0.0650 0.104 Uiso calc R 1 . .
C C17 0.4995(4) 0.5701(3) 0.3400(2) 0.0432(7) Uani d . 1 . .
H H17A 0.4114 0.5349 0.3842 0.065 Uiso calc R 1 . .
H H17B 0.6197 0.5438 0.3502 0.065 Uiso calc R 1 . .
H H17C 0.4224 0.5133 0.2800 0.065 Uiso calc R 1 . .
H H1A 0.760(4) 1.143(3) 0.582(2) 0.034(7) Uiso d . 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'
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
C3 O1 H1B . . 109.5 ?
C14 O3 C15 . . 117.9(2) ?
C6 O4 H4A . . 109.5 ?
H5B O5 H5C . . 105(4) ?
C7A N1 N2 . . 108.2(2) ?
C7A N1 H1A . . 130.0(17) ?
N2 N1 H1A . . 117.5(17) ?
C3 N2 N1 . . 107.5(2) ?
O1 C3 N2 . . 123.5(2) ?
O1 C3 C3A . . 126.8(2) ?
N2 C3 C3A . . 109.6(2) ?
C7A C3A C3 . . 104.3(2) ?
C7A C3A C4 . . 124.9(2) ?
C3 C3A C4 . . 130.6(2) ?
C3A C4 C8 . . 114.11(18) ?
C3A C4 C5 . . 109.1(2) ?
C8 C4 C5 . . 109.85(19) ?
C3A C4 H4B . . 107.8 ?
C8 C4 H4B . . 107.8 ?
C5 C4 H4B . . 107.8 ?
C14 C5 C4 . . 110.5(2) ?
C14 C5 C6 . . 111.47(18) ?
C4 C5 C6 . . 112.80(19) ?
C14 C5 H5A . . 107.2 ?
C4 C5 H5A . . 107.2 ?
C6 C5 H5A . . 107.2 ?
O4 C6 C17 . . 111.01(18) ?
O4 C6 C7 . . 106.04(18) ?
C17 C6 C7 . . 109.6(2) ?
O4 C6 C5 . . 110.4(2) ?
C17 C6 C5 . . 110.5(2) ?
C7 C6 C5 . . 109.18(18) ?
C7A C7 C6 . . 109.0(2) ?
C7A C7 H7A . . 109.9 ?
C6 C7 H7A . . 109.9 ?
C7A C7 H7B . . 109.9 ?
C6 C7 H7B . . 109.9 ?
H7A C7 H7B . . 108.3 ?
N1 C7A C3A . . 110.2(2) ?
N1 C7A C7 . . 124.8(2) ?
C3A C7A C7 . . 125.0(2) ?
C13 C8 C9 . . 117.9(3) ?
C13 C8 C4 . . 121.4(2) ?
C9 C8 C4 . . 120.6(2) ?
C10 C9 C8 . . 121.2(3) ?
C10 C9 H9A . . 119.4 ?
C8 C9 H9A . . 119.4 ?
C9 C10 C11 . . 120.2(3) ?
C9 C10 H10A . . 119.9 ?
C11 C10 H10A . . 119.9 ?
C10 C11 C12 . . 119.6(3) ?
C10 C11 H11A . . 120.2 ?
C12 C11 H11A . . 120.2 ?
C13 C12 C11 . . 119.6(4) ?
C13 C12 H12A . . 120.2 ?
C11 C12 H12A . . 120.2 ?
C8 C13 C12 . . 121.4(3) ?
C8 C13 H13A . . 119.3 ?
C12 C13 H13A . . 119.3 ?
O2 C14 O3 . . 123.6(2) ?
O2 C14 C5 . . 125.0(2) ?
O3 C14 C5 . . 111.4(2) ?
O3 C15 C16 . . 107.3(2) ?
O3 C15 H15A . . 110.3 ?
C16 C15 H15A . . 110.3 ?
O3 C15 H15B . . 110.3 ?
C16 C15 H15B . . 110.3 ?
H15A C15 H15B . . 108.5 ?
C15 C16 H16A . . 109.5 ?
C15 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C15 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
C6 C17 H17A . . 109.5 ?
C6 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C6 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
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 C3 . 1.308(3) ?
O1 H1B . 0.8200 ?
O2 C14 . 1.209(3) ?
O3 C14 . 1.321(3) ?
O3 C15 . 1.462(3) ?
O4 C6 . 1.425(3) ?
O4 H4A . 0.8200 ?
O5 H5B . 0.95(5) ?
O5 H5C . 0.85(4) ?
N1 C7A . 1.354(3) ?
N1 N2 . 1.379(3) ?
N1 H1A . 0.92(3) ?
N2 C3 . 1.326(4) ?
C3 C3A . 1.432(3) ?
C3A C7A . 1.355(4) ?
C3A C4 . 1.502(3) ?
C4 C8 . 1.514(3) ?
C4 C5 . 1.558(3) ?
C4 H4B . 0.9800 ?
C5 C14 . 1.517(3) ?
C5 C6 . 1.561(4) ?
C5 H5A . 0.9800 ?
C6 C17 . 1.526(3) ?
C6 C7 . 1.532(3) ?
C7 C7A . 1.493(3) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 C13 . 1.379(4) ?
C8 C9 . 1.394(4) ?
C9 C10 . 1.371(4) ?
C9 H9A . 0.9300 ?
C10 C11 . 1.378(5) ?
C10 H10A . 0.9300 ?
C11 C12 . 1.385(6) ?
C11 H11A . 0.9300 ?
C12 C13 . 1.381(5) ?
C12 H12A . 0.9300 ?
C13 H13A . 0.9300 ?
C15 C16 . 1.482(5) ?
C15 H15A . 0.9700 ?
C15 H15B . 0.9700 ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 0.9600 ?
C17 H17A . 0.9600 ?
C17 H17B . 0.9600 ?
C17 H17C . 0.9600 ?
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 H1B N2 8_655 0.82 1.89 2.705(2) 171 yes
O4 H4A O3 8_655 0.82 2.22 2.897(2) 141 yes
N1 H1A O4 5_665 0.93(3) 1.94 2.778(3) 155 yes
O5 H5B O1 8_655 0.95(5) 2.01 2.874(2) 165 yes
O5 H5C O2 5_665 0.84(4) 1.97 2.844(3) 179 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
C7A N1 N2 C3 . . . . -3.1(3) ?
N1 N2 C3 O1 . . . . -178.5(2) ?
N1 N2 C3 C3A . . . . 1.2(3) ?
O1 C3 C3A C7A . . . . -179.2(2) ?
N2 C3 C3A C7A . . . . 1.1(3) ?
O1 C3 C3A C4 . . . . -3.8(4) ?
N2 C3 C3A C4 . . . . 176.5(2) ?
C7A C3A C4 C8 . . . . -133.3(2) ?
C3 C3A C4 C8 . . . . 52.1(3) ?
C7A C3A C4 C5 . . . . -10.0(3) ?
C3 C3A C4 C5 . . . . 175.4(2) ?
C3A C4 C5 C14 . . . . 165.98(18) ?
C8 C4 C5 C14 . . . . -68.2(2) ?
C3A C4 C5 C6 . . . . 40.4(2) ?
C8 C4 C5 C6 . . . . 166.2(2) ?
C14 C5 C6 O4 . . . . -72.4(2) ?
C4 C5 C6 O4 . . . . 52.7(2) ?
C14 C5 C6 C17 . . . . 50.8(3) ?
C4 C5 C6 C17 . . . . 175.87(19) ?
C14 C5 C6 C7 . . . . 171.44(19) ?
C4 C5 C6 C7 . . . . -63.5(2) ?
O4 C6 C7 C7A . . . . -68.0(2) ?
C17 C6 C7 C7A . . . . 172.1(2) ?
C5 C6 C7 C7A . . . . 50.9(2) ?
N2 N1 C7A C3A . . . . 3.9(3) ?
N2 N1 C7A C7 . . . . -176.2(2) ?
C3 C3A C7A N1 . . . . -3.0(3) ?
C4 C3A C7A N1 . . . . -178.8(2) ?
C3 C3A C7A C7 . . . . 177.1(2) ?
C4 C3A C7A C7 . . . . 1.3(4) ?
C6 C7 C7A N1 . . . . 157.6(2) ?
C6 C7 C7A C3A . . . . -22.5(3) ?
C3A C4 C8 C13 . . . . -135.7(2) ?
C5 C4 C8 C13 . . . . 101.3(3) ?
C3A C4 C8 C9 . . . . 45.6(3) ?
C5 C4 C8 C9 . . . . -77.3(3) ?
C13 C8 C9 C10 . . . . 0.7(4) ?
C4 C8 C9 C10 . . . . 179.3(2) ?
C8 C9 C10 C11 . . . . -0.4(4) ?
C9 C10 C11 C12 . . . . 0.8(5) ?
C10 C11 C12 C13 . . . . -1.4(5) ?
C9 C8 C13 C12 . . . . -1.3(4) ?
C4 C8 C13 C12 . . . . -180.0(3) ?
C11 C12 C13 C8 . . . . 1.7(5) ?
C15 O3 C14 O2 . . . . 2.6(4) ?
C15 O3 C14 C5 . . . . -175.3(2) ?
C4 C5 C14 O2 . . . . 126.8(3) ?
C6 C5 C14 O2 . . . . -106.9(3) ?
C4 C5 C14 O3 . . . . -55.4(3) ?
C6 C5 C14 O3 . . . . 70.9(3) ?
C14 O3 C15 C16 . . . . -172.8(3) ?
