#------------------------------------------------------------------------------
#$Date: 2019-11-08 03:28:57 +0200 (Fri, 08 Nov 2019) $
#$Revision: 225076 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/69/7156985.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7156985
loop_
_publ_author_name
'Yuan, Yu-Chao'
'Bruneau, Christian'
'Roisnel, Thierry'
'Gramage-Doria, Rafael'
_publ_section_title
;
 Ruthenium(ii)-catalysed selective C(sp²)-H bond benzoxylation
 of biologically appealing N-arylisoindolinones.
;
_journal_issue                   32
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              7517
_journal_page_last               7525
_journal_paper_doi               10.1039/c9ob01122f
_journal_volume                  17
_journal_year                    2019
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C21 H15 N O3'
_chemical_formula_sum            'C21 H15 N O3'
_chemical_formula_weight         329.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_update_record
;
2019-04-15 deposited with the CCDC.    2019-07-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.487(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.076(4)
_cell_length_b                   8.828(3)
_cell_length_c                   11.834(3)
_cell_measurement_reflns_used    2248
_cell_measurement_temperature    150
_cell_measurement_theta_max      27.6383
_cell_measurement_theta_min      2.6058
_cell_measurement_wavelength     0.71073
_cell_volume                     1633.2(8)
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_collection       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics
'SXGRAPH (Farrugia, 1999), Mercury (CSD, 2016)'
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2019)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0909
_diffrn_reflns_av_unetI/netI     0.0769
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8256
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.751
_diffrn_reflns_theta_min         2.606
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.746
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_description       plate
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.008(2)
_refine_ls_extinction_method     'SHELXL-2018_3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     113
_refine_ls_number_reflns         1874
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.1441
_refine_ls_R_factor_gt           0.0841
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0915P)²+2.5744P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2021
_refine_ls_wR_factor_ref         0.2340
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1082
_reflns_number_total             1874
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9ob01122f2.cif
_cod_data_source_block           RGYYC477
_cod_depositor_comments
'Adding full bibliography for 7156985--7156989.cif.'
_cod_database_code               7156985
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1A O 0.63680(16) 0.6415(3) 0.2133(2) 0.0667(9) Uani 0.5 1 d . . P A 1
C2A C 0.6186(2) 0.6704(5) 0.3050(3) 0.0560(10) Uani 0.5 1 d . . P A 1
C3A C 0.64952(14) 0.7977(3) 0.38144(17) 0.0546(10) Uani 0.5 1 d G . P A 1
C4A C 0.71011(13) 0.9017(3) 0.36355(16) 0.0594(11) Uani 0.5 1 d G . P A 1
H4A H 0.734309 0.891961 0.297938 0.071 Uiso 0.5 1 calc R U P A 1
C5A C 0.73530(14) 1.0198(3) 0.44166(19) 0.0654(13) Uani 0.5 1 d G . P A 1
H5A H 0.776711 1.090890 0.429430 0.079 Uiso 0.5 1 calc R U P A 1
C6A C 0.69989(17) 1.0341(3) 0.53766(19) 0.0744(14) Uani 0.5 1 d G . P A 1
H6A H 0.717108 1.114823 0.591045 0.089 Uiso 0.5 1 calc R U P A 1
C7A C 0.63930(16) 0.9301(4) 0.55556(17) 0.0841(16) Uani 0.5 1 d G . P A 1
H7A H 0.615103 0.939829 0.621170 0.101 Uiso 0.5 1 calc R U P A 1
C8A C 0.61411(14) 0.8119(3) 0.47745(19) 0.0728(14) Uani 0.5 1 d G . P A 1
C9A C 0.5646(4) 0.6543(9) 0.4584(5) 0.0508(18) Uani 0.5 1 d . . P A 1
H9A H 0.591252 0.584974 0.522458 0.061 Uiso 0.5 1 calc R U P A 1
H9B H 0.504708 0.671320 0.463286 0.061 Uiso 0.5 1 calc R U P A 1
N10A N 0.56438(16) 0.5846(3) 0.3542(2) 0.0530(8) Uani 0.5 1 d . . P A 1
C11A C 0.53228(18) 0.4492(4) 0.3010(2) 0.0435(9) Uani 0.5 1 d . . P A 1
C12A C 0.56281(19) 0.3143(5) 0.3515(3) 0.0561(10) Uani 0.5 1 d . . P A 1
H12A H 0.606123 0.314084 0.421492 0.067 Uiso 0.5 1 calc R U P A 1
C13A C 0.5313(2) 0.1798(5) 0.3016(4) 0.0669(12) Uani 0.5 1 d . . P A 1
H13A H 0.552(3) 0.091(5) 0.336(4) 0.080 Uiso 0.5 1 d . U P B 1
O1B O 0.63680(16) 0.6415(3) 0.2133(2) 0.0667(9) Uani 0.5 1 d . . P C 2
C2B C 0.6186(2) 0.6704(5) 0.3050(3) 0.0560(10) Uani 0.5 1 d . . P C 2
C3B C 0.64952(14) 0.7977(3) 0.38144(17) 0.0546(10) Uani 0.5 1 d G . P C 2
C4B C 0.71011(13) 0.9017(3) 0.36355(16) 0.0594(11) Uani 0.5 1 d G . P C 2
H4B H 0.734309 0.891961 0.297938 0.071 Uiso 0.5 1 calc R U P C 2
C5B C 0.73530(14) 1.0198(3) 0.44166(19) 0.0654(13) Uani 0.5 1 d G . P C 2
H5B H 0.776711 1.090890 0.429430 0.079 Uiso 0.5 1 calc R U P C 2
C6B C 0.69989(17) 1.0341(3) 0.53766(19) 0.0744(14) Uani 0.5 1 d G . P C 2
H6B H 0.717108 1.114823 0.591045 0.089 Uiso 0.5 1 calc R U P C 2
C7B C 0.63930(16) 0.9301(4) 0.55556(17) 0.0841(16) Uani 0.5 1 d G . P C 2
H7B H 0.615103 0.939829 0.621170 0.101 Uiso 0.5 1 calc R U P C 2
C8B C 0.61411(14) 0.8119(3) 0.47745(19) 0.0728(14) Uani 0.5 1 d G . P C 2
H8B H 0.572700 0.740898 0.489680 0.087 Uiso 0.5 1 calc R U P C 2
O10B O 0.56438(16) 0.5846(3) 0.3542(2) 0.0530(8) Uani 0.5 1 d . . P C 2
C11B C 0.53228(18) 0.4492(4) 0.3010(2) 0.0435(9) Uani 0.5 1 d . . P C 2
C12B C 0.56281(19) 0.3143(5) 0.3515(3) 0.0561(10) Uani 0.5 1 d . . P C 2
H12B H 0.606123 0.314084 0.421492 0.067 Uiso 0.5 1 calc R U P C 2
C13B C 0.5313(2) 0.1798(5) 0.3016(4) 0.0669(12) Uani 0.5 1 d . . P C 2
H13B H 0.552(3) 0.091(5) 0.336(4) 0.080 Uiso 0.5 1 d . U P D 2
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O1A C2A N10A 124.6(4) . .
O1A C2A C3A 126.8(3) . .
N10A C2A C3A 108.6(3) . .
C4A C3A C8A 120.0 . .
C4A C3A C2A 124.4(2) . .
C8A C3A C2A 115.6(2) . .
C5A C4A C3A 120.0 . .
C5A C4A H4A 120.0 . .
C3A C4A H4A 120.0 . .
C4A C5A C6A 120.0 . .
C4A C5A H5A 120.0 . .
C6A C5A H5A 120.0 . .
C7A C6A C5A 120.0 . .
C7A C6A H6A 120.0 . .
C5A C6A H6A 120.0 . .
C6A C7A C8A 120.0 . .
C6A C7A H7A 120.0 . .
C8A C7A H7A 120.0 . .
C7A C8A C3A 120.0 . .
C7A C8A C9A 143.9(3) . .
C3A C8A C9A 95.3(3) . .
N10A C9A C8A 114.4(4) . .
N10A C9A H9A 108.6 . .
C8A C9A H9A 108.6 . .
N10A C9A H9B 108.6 . .
C8A C9A H9B 108.6 . .
H9A C9A H9B 107.6 . .
C9A N10A C2A 105.1(4) . .
C9A N10A C11A 135.3(4) . .
C2A N10A C11A 119.0(3) . .
C12A C11A N10A 119.4(3) . .
C12A C11A C11A 119.68(19) . 2_655
N10A C11A C11A 120.86(16) . 2_655
C13A C12A C11A 120.4(3) . .
C13A C12A H12A 119.8 . .
C11A C12A H12A 119.8 . .
C12A C13A C13A 119.9(2) . 2_655
C12A C13A H13A 119(3) . .
C13A C13A H13A 121(3) 2_655 .
O1B C2B O10B 124.6(4) . .
O1B C2B C3B 126.8(3) . .
O10B C2B C3B 108.6(3) . .
C4B C3B C8B 120.0 . .
C4B C3B C2B 124.4(2) . .
C8B C3B C2B 115.6(2) . .
C5B C4B C3B 120.0 . .
C5B C4B H4B 120.0 . .
C3B C4B H4B 120.0 . .
C4B C5B C6B 120.0 . .
C4B C5B H5B 120.0 . .
C6B C5B H5B 120.0 . .
C7B C6B C5B 120.0 . .
C7B C6B H6B 120.0 . .
C5B C6B H6B 120.0 . .
C6B C7B C8B 120.0 . .
C6B C7B H7B 120.0 . .
C8B C7B H7B 120.0 . .
C7B C8B C3B 120.0 . .
C7B C8B H8B 120.0 . .
C3B C8B H8B 120.0 . .
C2B O10B C11B 119.0(3) . .
C12B C11B O10B 119.4(3) . .
C13B C12B C11B 120.4(3) . .
C13B C12B H12B 119.8 . .
C11B C12B H12B 119.8 . .
C12B C13B H13B 119(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1A C2A 1.216(4) .
C2A N10A 1.382(5) .
C2A C3A 1.455(4) .
C3A C4A 1.3900 .
C3A C8A 1.3900 .
C4A C5A 1.3900 .
C4A H4A 0.9500 .
C5A C6A 1.3900 .
C5A H5A 0.9500 .
C6A C7A 1.3900 .
C6A H6A 0.9500 .
C7A C8A 1.3900 .
C7A H7A 0.9500 .
C8A C9A 1.593(7) .
C9A N10A 1.378(7) .
C9A H9A 0.9900 .
C9A H9B 0.9900 .
N10A C11A 1.393(4) .
C11A C12A 1.371(5) .
C11A C11A 1.396(5) 2_655
C12A C13A 1.370(6) .
C12A H12A 0.9500 .
C13A C13A 1.389(7) 2_655
C13A H13A 0.91(5) .
O1B C2B 1.216(4) .
C2B O10B 1.382(5) .
C2B C3B 1.455(4) .
C3B C4B 1.3900 .
C3B C8B 1.3900 .
C4B C5B 1.3900 .
C4B H4B 0.9500 .
C5B C6B 1.3900 .
C5B H5B 0.9500 .
C6B C7B 1.3900 .
C6B H6B 0.9500 .
C7B C8B 1.3900 .
C7B H7B 0.9500 .
C8B H8B 0.9500 .
O10B C11B 1.393(4) .
C11B C12B 1.371(5) .
C12B C13B 1.370(6) .
C12B H12B 0.9500 .
C13B H13B 0.91(5) .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
O1A C2A C3A C4A -4.5(5) . .
N10A C2A C3A C4A 175.22(19) . .
O1A C2A C3A C8A 175.4(3) . .
N10A C2A C3A C8A -4.9(3) . .
C8A C3A C4A C5A 0.0 . .
C2A C3A C4A C5A 179.9(3) . .
C3A C4A C5A C6A 0.0 . .
C4A C5A C6A C7A 0.0 . .
C5A C6A C7A C8A 0.0 . .
C6A C7A C8A C3A 0.0 . .
C6A C7A C8A C9A 166.5(5) . .
C4A C3A C8A C7A 0.0 . .
C2A C3A C8A C7A -179.9(2) . .
C4A C3A C8A C9A -172.1(3) . .
C2A C3A C8A C9A 8.1(3) . .
C7A C8A C9A N10A -177.8(2) . .
C3A C8A C9A N10A -9.6(5) . .
C8A C9A N10A C2A 7.4(6) . .
C8A C9A N10A C11A 178.5(3) . .
O1A C2A N10A C9A 177.8(4) . .
C3A C2A N10A C9A -1.9(4) . .
O1A C2A N10A C11A 4.9(5) . .
C3A C2A N10A C11A -174.8(2) . .
C9A N10A C11A C12A -63.0(6) . .
C2A N10A C11A C12A 107.1(3) . .
C9A N10A C11A C11A 115.1(6) . 2_655
C2A N10A C11A C11A -74.8(4) . 2_655
N10A C11A C12A C13A 179.1(3) . .
C11A C11A C12A C13A 1.0(6) 2_655 .
C11A C12A C13A C13A 0.8(8) . 2_655
O1B C2B C3B C4B -4.5(5) . .
O10B C2B C3B C4B 175.22(19) . .
O1B C2B C3B C8B 175.4(3) . .
O10B C2B C3B C8B -4.9(3) . .
C8B C3B C4B C5B 0.0 . .
C2B C3B C4B C5B 179.9(3) . .
C3B C4B C5B C6B 0.0 . .
C4B C5B C6B C7B 0.0 . .
C5B C6B C7B C8B 0.0 . .
C6B C7B C8B C3B 0.0 . .
C4B C3B C8B C7B 0.0 . .
C2B C3B C8B C7B -179.9(2) . .
O1B C2B O10B C11B 4.9(5) . .
C3B C2B O10B C11B -174.8(2) . .
C2B O10B C11B C12B 107.1(3) . .
O10B C11B C12B C13B 179.1(3) . .
