#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/09/2210991.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_2210991
loop_
_publ_author_name
'Brito-Arias, Marco'
'Castillo-Juárez, Karla'
'Molins, Elies'
_publ_section_title
;
 3-Benzoyl-4-hydroxyisoquinolin-1(2H)-one
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o5261
_journal_page_last               o5262
_journal_paper_doi               10.1107/S1600536806043571
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C16 H11 N1 O3'
_chemical_formula_moiety         'C16 H11 N1 O3'
_chemical_formula_sum            'C16 H11 N O3'
_chemical_formula_weight         265.26
_chemical_name_systematic
;
3-Benzoyl-4-hydroxy-2H-isoquinolin-1-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.2
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 102.39(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.951(3)
_cell_length_b                   17.803(6)
_cell_length_c                   12.018(2)
_cell_measurement_reflns_used    15
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      9.3
_cell_measurement_theta_min      5.7
_cell_volume                     1243.6(8)
_computing_cell_refinement       'CAD-4 Express'
_computing_data_collection       'CAD-4 Express (Enraf--Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       'Non-profiled omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.031
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2278
_diffrn_reflns_theta_full        24.97
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_min         2.08
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         1
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_correction_T_min  0.948
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details
;
(Walker & Stuart (1983) Acta Cryst. A39, 158-166)
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.118
_refine_diff_density_min         -0.179
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2175
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0888
_refine_ls_R_factor_gt           0.0415
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0539P)²+0.1111P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.102
_refine_ls_wR_factor_ref         0.1174
_reflns_number_gt                1406
_reflns_number_total             2175
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            fl2049.cif
_cod_data_source_block           I
_cod_original_cell_volume        1243.7(8)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2210991
_cod_database_fobs_code          2210991
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
C C1 0.0041(3) 1.01551(12) 0.33471(17) 0.0478(5) Uani d . 1
C C3 0.3364(3) 0.93458(12) 0.33495(17) 0.0473(5) Uani d . 1
C C4 0.3626(4) 0.96322(13) 0.23213(18) 0.0522(6) Uani d . 1
C C5 0.2360(4) 1.05180(14) 0.07116(19) 0.0640(7) Uani d . 1
H H5 0.3571 1.0369 0.0385 0.077 Uiso calc R 1
C C6 0.0831(5) 1.10457(15) 0.0188(2) 0.0725(8) Uani d . 1
H H6 0.1019 1.1258 -0.0493 0.087 Uiso calc R 1
C C7 -0.0996(5) 1.12699(14) 0.0655(2) 0.0714(7) Uani d . 1
H H7 -0.2039 1.1623 0.0277 0.086 Uiso calc R 1
C C8 -0.1278(4) 1.09722(13) 0.16755(19) 0.0586(6) Uani d . 1
H H8 -0.2493 1.1129 0.1994 0.07 Uiso calc R 1
C C9 0.0279(4) 1.04331(11) 0.22280(17) 0.0474(5) Uani d . 1
C C10 0.2098(4) 1.02001(13) 0.17454(17) 0.0506(5) Uani d . 1
C C11 0.4875(3) 0.87651(13) 0.39250(18) 0.0527(6) Uani d . 1
C C12 0.4498(3) 0.83840(12) 0.49665(18) 0.0465(5) Uani d . 1
C C13 0.6372(4) 0.82842(13) 0.5867(2) 0.0577(6) Uani d . 1
H H13 0.7796 0.8482 0.5822 0.069 Uiso calc R 1
C C14 0.6143(4) 0.78963(14) 0.6826(2) 0.0661(7) Uani d . 1
H H14 0.74 0.7842 0.7432 0.079 Uiso calc R 1
C C15 0.4063(4) 0.75893(13) 0.6888(2) 0.0637(7) Uani d . 1
H H15 0.3916 0.7322 0.7534 0.076 Uiso calc R 1
C C16 0.2195(4) 0.76744(13) 0.6004(2) 0.0601(6) Uani d . 1
H H16 0.0793 0.7458 0.6046 0.072 Uiso calc R 1
C C17 0.2392(3) 0.80809(12) 0.50510(19) 0.0528(6) Uani d . 1
H H17 0.111 0.8152 0.4464 0.063 Uiso calc R 1
N N2 0.1612(3) 0.96390(10) 0.38404(14) 0.0484(5) Uani d . 1
H H2 0.1532 0.9478 0.4506 0.058 Uiso calc R 1
O O1 -0.1460(3) 1.03900(8) 0.38354(12) 0.0601(4) Uani d . 1
O O4 0.5270(3) 0.93872(11) 0.18061(13) 0.0712(5) Uani d . 1
H H4 0.617 0.9119 0.2245 0.107 Uiso calc R 1
O O11 0.6576(3) 0.85705(10) 0.35400(15) 0.0759(5) Uani 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
2 -7 2
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
O1 C1 N2 121.40(19) y
O1 C1 C9 122.67(19) ?
N2 C1 C9 115.90(18) ?
C4 C3 N2 118.48(19) y
C4 C3 C11 121.07(19) ?
N2 C3 C11 120.44(19) y
O4 C4 C3 122.0(2) y
O4 C4 C10 117.20(19) ?
C3 C4 C10 120.81(19) ?
C6 C5 C10 119.7(2) ?
C6 C5 H5 120.1 ?
C10 C5 H5 120.1 ?
C5 C6 C7 121.1(2) ?
C5 C6 H6 119.5 ?
C7 C6 H6 119.5 ?
C8 C7 C6 120.3(2) ?
C8 C7 H7 119.8 ?
C6 C7 H7 119.8 ?
C7 C8 C9 119.4(2) ?
C7 C8 H8 120.3 ?
C9 C8 H8 120.3 ?
C10 C9 C8 120.0(2) ?
C10 C9 C1 121.1(2) ?
C8 C9 C1 118.8(2) ?
C9 C10 C5 119.4(2) ?
C9 C10 C4 118.47(19) ?
C5 C10 C4 122.1(2) ?
O11 C11 C3 119.4(2) y
O11 C11 C12 117.9(2) y
C3 C11 C12 122.69(18) y
C17 C12 C13 118.7(2) ?
C17 C12 C11 122.8(2) ?
C13 C12 C11 118.36(18) ?
C14 C13 C12 120.7(2) ?
C14 C13 H13 119.7 ?
C12 C13 H13 119.7 ?
C15 C14 C13 119.9(2) ?
C15 C14 H14 120.0 ?
C13 C14 H14 120.0 ?
C14 C15 C16 120.4(2) ?
C14 C15 H15 119.8 ?
C16 C15 H15 119.8 ?
C15 C16 C17 120.1(2) ?
C15 C16 H16 120.0 ?
C17 C16 H16 119.9 ?
C16 C17 C12 120.2(2) ?
C16 C17 H17 119.9 ?
C12 C17 H17 119.9 ?
C1 N2 C3 125.02(18) y
C1 N2 H2 117.5 ?
C3 N2 H2 117.5 ?
C4 O4 H4 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O1 1.242(2) y
C1 N2 1.353(2) y
C1 C9 1.468(3) ?
C3 C4 1.376(3) y
C3 N2 1.404(2) y
C3 C11 1.445(3) y
C4 O4 1.338(2) y
C4 C10 1.434(3) ?
C5 C6 1.364(3) ?
C5 C10 1.404(3) ?
C5 H5 0.9300 ?
C6 C7 1.385(3) ?
C6 H6 0.9300 ?
C7 C8 1.379(3) ?
C7 H7 0.9300 ?
C8 C9 1.399(3) ?
C8 H8 0.9300 ?
C9 C10 1.396(3) ?
C11 O11 1.249(2) y
C11 C12 1.483(3) y
C12 C17 1.388(3) ?
C12 C13 1.389(3) ?
C13 C14 1.375(3) ?
C13 H13 0.9300 ?
C14 C15 1.370(3) ?
C14 H14 0.9300 ?
C15 C16 1.372(3) ?
C15 H15 0.9300 ?
C16 C17 1.381(3) ?
C16 H16 0.9300 ?
C17 H17 0.9300 ?
N2 H2 0.8600 ?
O4 H4 0.8200 ?
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
N2 H2 O1 3_576 0.86 2.02 2.815(2) 153.8
O4 H4 O11 . 0.82 1.81 2.523(2) 144.8
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
N2 C3 C4 O4 179.29(19)
C11 C3 C4 O4 0.3(3)
N2 C3 C4 C10 -2.0(3)
C11 C3 C4 C10 179.00(19)
C10 C5 C6 C7 -0.6(4)
C5 C6 C7 C8 1.3(4)
C6 C7 C8 C9 -1.0(4)
C7 C8 C9 C10 -0.1(3)
C7 C8 C9 C1 176.3(2)
O1 C1 C9 C10 174.85(19)
N2 C1 C9 C10 -3.1(3)
O1 C1 C9 C8 -1.5(3)
N2 C1 C9 C8 -179.47(18)
C8 C9 C10 C5 0.7(3)
C1 C9 C10 C5 -175.56(19)
C8 C9 C10 C4 -178.4(2)
C1 C9 C10 C4 5.3(3)
C6 C5 C10 C9 -0.4(3)
C6 C5 C10 C4 178.7(2)
O4 C4 C10 C9 176.09(18)
C3 C4 C10 C9 -2.7(3)
O4 C4 C10 C5 -3.0(3)
C3 C4 C10 C5 178.2(2)
C4 C3 C11 O11 6.9(3)
N2 C3 C11 O11 -172.09(19)
C4 C3 C11 C12 -173.2(2)
N2 C3 C11 C12 7.9(3)
O11 C11 C12 C17 -130.5(2)
C3 C11 C12 C17 49.6(3)
O11 C11 C12 C13 45.2(3)
C3 C11 C12 C13 -134.7(2)
C17 C12 C13 C14 -0.3(3)
C11 C12 C13 C14 -176.2(2)
C12 C13 C14 C15 1.5(4)
C13 C14 C15 C16 -0.8(4)
C14 C15 C16 C17 -1.0(4)
C15 C16 C17 C12 2.1(3)
C13 C12 C17 C16 -1.5(3)
C11 C12 C17 C16 174.2(2)
O1 C1 N2 C3 -179.86(19)
C9 C1 N2 C3 -1.9(3)
C4 C3 N2 C1 4.4(3)
C11 C3 N2 C1 -176.56(19)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21126213
