#------------------------------------------------------------------------------
#$Date: 2022-05-11 03:35:36 +0300 (Wed, 11 May 2022) $
#$Revision: 275316 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/86/7158691.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_7158691
loop_
_publ_author_name
'Zhaojiang, Shi'
'Li, Nan'
'Wang, Wei-Zhen'
'Lu, Hao-Kuan'
'Yuan, Yaofeng'
'Li, Zhen'
'Ye, Ke-Yin'
_publ_section_title
;
 Electrochemical 5-exo-dig aza-cyclization of 2-alkynylbenzamides toward
 3-hydroxyisoindolinone derivatives
;
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB00637E
_journal_year                    2022
_chemical_formula_moiety         'C15 H9 Br O2'
_chemical_formula_sum            'C15 H9 Br O2'
_chemical_formula_weight         301.13
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-10-01
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2021-10-13 deposited with the CCDC.	2022-05-09 downloaded from the CCDC.
;
_cell_angle_alpha                104.92(6)
_cell_angle_beta                 94.22(7)
_cell_angle_gamma                111.29(6)
_cell_formula_units_Z            2
_cell_length_a                   7.106(10)
_cell_length_b                   7.215(11)
_cell_length_c                   13.194(19)
_cell_measurement_reflns_used    4887
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      24.683
_cell_measurement_theta_min      3.099
_cell_volume                     598.5(16)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0749
_diffrn_reflns_av_unetI/netI     0.0472
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12879
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.109
_diffrn_reflns_theta_max         25.109
_diffrn_reflns_theta_min         3.100
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    3.423
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.4856
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1361 before and 0.0726 after correction.
The Ratio of minimum to maximum transmission is 0.6516.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.671
_exptl_crystal_description       plate
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.740
_refine_diff_density_min         -0.843
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2123
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0423
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0589P)²+0.1058P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0973
_refine_ls_wR_factor_ref         0.1036
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1749
_reflns_number_total             2123
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob00637e2.cif
_cod_data_source_block           ln22u2_0m
_cod_original_cell_volume        598.4(16)
_cod_database_code               7158691
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.726
_shelx_estimated_absorpt_t_min   0.548
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H008), C12(H009), C15(H00B), C14(H00C), C11(H00D), C6(H00E), C3(H00G),
 C5(H00H), C4(H00I)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
Br1 Br 0.68276(6) 0.35500(6) 0.93941(3) 0.0457(2) Uani 1 1 d . . . . .
O2 O 0.2426(3) 0.4558(3) 0.49367(19) 0.0271(5) Uani 1 1 d . . . . .
O1 O 0.1348(4) 0.6391(4) 0.4120(2) 0.0359(6) Uani 1 1 d . . . . .
C9 C 0.2548(5) 0.2709(5) 0.4992(3) 0.0245(7) Uani 1 1 d . . . . .
C10 C 0.3531(5) 0.2906(5) 0.6055(3) 0.0262(8) Uani 1 1 d . . . . .
C7 C 0.0851(5) 0.1045(5) 0.3151(3) 0.0257(8) Uani 1 1 d . . . . .
C2 C 0.0595(5) 0.2863(5) 0.3115(3) 0.0267(8) Uani 1 1 d . . . . .
C8 C 0.1816(5) 0.1012(5) 0.4135(3) 0.0258(7) Uani 1 1 d . . . . .
H008 H 0.193542 -0.020839 0.417785 0.031 Uiso 1 1 calc R U . . .
C12 C 0.5105(5) 0.4956(6) 0.7886(3) 0.0345(9) Uani 1 1 d . . . . .
H009 H 0.549618 0.619403 0.844112 0.041 Uiso 1 1 calc R U . . .
C13 C 0.5473(5) 0.3291(6) 0.8043(3) 0.0320(8) Uani 1 1 d . . . . .
C15 C 0.3898(5) 0.1234(5) 0.6243(3) 0.0289(8) Uani 1 1 d . . . . .
H00B H 0.348523 -0.001683 0.569439 0.035 Uiso 1 1 calc R U . . .
C14 C 0.4861(5) 0.1418(6) 0.7229(3) 0.0312(8) Uani 1 1 d . . . . .
H00C H 0.509789 0.029977 0.734942 0.037 Uiso 1 1 calc R U . . .
C11 C 0.4142(5) 0.4752(6) 0.6886(3) 0.0291(8) Uani 1 1 d . . . . .
H00D H 0.390149 0.587281 0.677065 0.035 Uiso 1 1 calc R U . . .
C6 C 0.0120(5) -0.0673(5) 0.2228(3) 0.0301(8) Uani 1 1 d . . . . .
H00E H 0.027766 -0.189341 0.223692 0.036 Uiso 1 1 calc R U . . .
C1 C 0.1430(5) 0.4723(6) 0.4050(3) 0.0274(8) Uani 1 1 d . . . . .
C3 C -0.0374(5) 0.2943(6) 0.2183(3) 0.0332(9) Uani 1 1 d . . . . .
H00G H -0.054104 0.415625 0.216715 0.040 Uiso 1 1 calc R U . . .
C5 C -0.0825(5) -0.0585(6) 0.1309(3) 0.0365(9) Uani 1 1 d . . . . .
H00H H -0.129303 -0.173975 0.069991 0.044 Uiso 1 1 calc R U . . .
C4 C -0.1089(5) 0.1222(6) 0.1280(3) 0.0396(9) Uani 1 1 d . . . . .
H00I H -0.174339 0.127112 0.065602 0.048 Uiso 1 1 calc R U . . .
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'
Br Br -0.2901 2.4595 '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
_geom_angle_publ_flag
C1 O2 C9 123.2(3) . . ?
O2 C9 C10 112.3(3) . . ?
C8 C9 O2 120.3(3) . . ?
C8 C9 C10 127.4(3) . . ?
C15 C10 C9 120.3(3) . . ?
C11 C10 C9 120.9(3) . . ?
C11 C10 C15 118.7(3) . . ?
C2 C7 C8 118.8(3) . . ?
C6 C7 C2 118.3(3) . . ?
C6 C7 C8 122.9(3) . . ?
C7 C2 C1 119.8(3) . . ?
C3 C2 C7 120.6(3) . . ?
C3 C2 C1 119.5(3) . . ?
C9 C8 C7 121.0(3) . . ?
C9 C8 H008 119.5 . . ?
C7 C8 H008 119.5 . . ?
C13 C12 H009 120.5 . . ?
C13 C12 C11 118.9(3) . . ?
C11 C12 H009 120.5 . . ?
C12 C13 Br1 119.6(3) . . ?
C12 C13 C14 121.3(4) . . ?
C14 C13 Br1 119.1(3) . . ?
C10 C15 H00B 119.6 . . ?
C14 C15 C10 120.8(3) . . ?
C14 C15 H00B 119.6 . . ?
C13 C14 H00C 120.4 . . ?
C15 C14 C13 119.2(3) . . ?
C15 C14 H00C 120.4 . . ?
C10 C11 C12 121.0(4) . . ?
C10 C11 H00D 119.5 . . ?
C12 C11 H00D 119.5 . . ?
C7 C6 H00E 119.5 . . ?
C5 C6 C7 120.9(3) . . ?
C5 C6 H00E 119.5 . . ?
O2 C1 C2 116.6(3) . . ?
O1 C1 O2 116.7(3) . . ?
O1 C1 C2 126.6(3) . . ?
C2 C3 H00G 120.0 . . ?
C4 C3 C2 120.1(4) . . ?
C4 C3 H00G 120.0 . . ?
C6 C5 H00H 119.8 . . ?
C6 C5 C4 120.5(3) . . ?
C4 C5 H00H 119.8 . . ?
C3 C4 C5 119.6(4) . . ?
C3 C4 H00I 120.2 . . ?
C5 C4 H00I 120.2 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C13 1.894(5) . ?
O2 C9 1.388(4) . ?
O2 C1 1.377(5) . ?
O1 C1 1.205(4) . ?
C9 C10 1.468(5) . ?
C9 C8 1.336(5) . ?
C10 C15 1.399(5) . ?
C10 C11 1.386(5) . ?
C7 C2 1.400(5) . ?
C7 C8 1.433(5) . ?
C7 C6 1.397(5) . ?
C2 C1 1.462(6) . ?
C2 C3 1.389(5) . ?
C8 H008 0.9300 . ?
C12 H009 0.9300 . ?
C12 C13 1.379(6) . ?
C12 C11 1.388(5) . ?
C13 C14 1.387(6) . ?
C15 H00B 0.9300 . ?
C15 C14 1.376(5) . ?
C14 H00C 0.9300 . ?
C11 H00D 0.9300 . ?
C6 H00E 0.9300 . ?
C6 C5 1.370(5) . ?
C3 H00G 0.9300 . ?
C3 C4 1.382(6) . ?
C5 H00H 0.9300 . ?
C5 C4 1.393(6) . ?
C4 H00I 0.9300 . ?
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C13 C14 C15 -179.2(2) . . . . ?
O2 C9 C10 C15 -176.2(3) . . . . ?
O2 C9 C10 C11 2.8(4) . . . . ?
O2 C9 C8 C7 -1.5(5) . . . . ?
C9 O2 C1 O1 176.5(3) . . . . ?
C9 O2 C1 C2 -4.0(4) . . . . ?
C9 C10 C15 C14 178.5(3) . . . . ?
C9 C10 C11 C12 -178.8(3) . . . . ?
C10 C9 C8 C7 178.6(3) . . . . ?
C10 C15 C14 C13 -0.1(5) . . . . ?
C7 C2 C1 O2 -0.7(4) . . . . ?
C7 C2 C1 O1 178.7(3) . . . . ?
C7 C2 C3 C4 -0.2(5) . . . . ?
C7 C6 C5 C4 -0.5(5) . . . . ?
C2 C7 C8 C9 -3.1(5) . . . . ?
C2 C7 C6 C5 0.0(5) . . . . ?
C2 C3 C4 C5 -0.3(5) . . . . ?
C8 C9 C10 C15 3.7(5) . . . . ?
C8 C9 C10 C11 -177.3(3) . . . . ?
C8 C7 C2 C1 4.1(4) . . . . ?
C8 C7 C2 C3 -178.6(3) . . . . ?
C8 C7 C6 C5 178.9(3) . . . . ?
C12 C13 C14 C15 1.1(5) . . . . ?
C13 C12 C11 C10 0.7(5) . . . . ?
C15 C10 C11 C12 0.2(5) . . . . ?
C11 C10 C15 C14 -0.5(5) . . . . ?
C11 C12 C13 Br1 178.9(2) . . . . ?
C11 C12 C13 C14 -1.4(5) . . . . ?
C6 C7 C2 C1 -177.0(3) . . . . ?
C6 C7 C2 C3 0.3(5) . . . . ?
C6 C7 C8 C9 178.1(3) . . . . ?
C6 C5 C4 C3 0.6(5) . . . . ?
C1 O2 C9 C10 -174.9(3) . . . . ?
C1 O2 C9 C8 5.2(4) . . . . ?
C1 C2 C3 C4 177.1(3) . . . . ?
C3 C2 C1 O2 -178.1(3) . . . . ?
C3 C2 C1 O1 1.4(5) . . . . ?
