#------------------------------------------------------------------------------
#$Date: 2019-11-17 14:50:27 +0200 (Sun, 17 Nov 2019) $
#$Revision: 230627 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/64/7156468.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_7156468
loop_
_publ_author_name
'Huang, Songhai'
'Niu, Pengfei'
'Su, Yingpeng'
'Hu, Dongcheng'
'Huo, Congde'
_publ_section_title
;
 Tandem radical cyclization of N-methacryloyl benzamides with
 CBr₄ to construct brominated isoquinolinediones.
;
_journal_issue                   41
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              7748
_journal_page_last               7752
_journal_paper_doi               10.1039/c8ob01964a
_journal_volume                  16
_journal_year                    2018
_chemical_formula_sum            'C12 H12 Br N O2'
_chemical_formula_weight         282.14
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-03-15 deposited with the CCDC.
2018-10-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.553(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.8559(6)
_cell_length_b                   13.8455(12)
_cell_length_c                   12.3109(11)
_cell_measurement_reflns_used    7819
_cell_measurement_temperature    571(2)
_cell_measurement_theta_max      28.25
_cell_measurement_theta_min      2.94
_cell_volume                     1158.45(18)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      571(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0583
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12516
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         2.942
_exptl_absorpt_coefficient_mu    3.532
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.618
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.506
_refine_diff_density_min         -0.701
_refine_diff_density_rms         0.097
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2244
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0715
_refine_ls_R_factor_gt           0.0573
_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)+(0.0555P)²+3.3909P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1340
_refine_ls_wR_factor_ref         0.1412
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1898
_reflns_number_total             2244
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8ob01964a2.cif
_cod_data_source_block           mo_20180126C_0m_a
_cod_depositor_comments          'Adding full bibliography for 7156468.cif.'
_cod_database_code               7156468
_shelx_shelxl_version_number     2014/7
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
Br1 Br 0.71433(8) 0.83576(4) 0.29013(5) 0.0580(2) Uani 1 1 d . .
C1 C 0.2075(7) 0.7160(3) 0.2487(4) 0.0394(11) Uani 1 1 d . .
H1 H 0.1703 0.7600 0.2992 0.047 Uiso 1 1 calc R U
C2 C 0.0877(7) 0.7013(4) 0.1517(4) 0.0463(12) Uani 1 1 d . .
H2 H -0.0280 0.7367 0.1362 0.056 Uiso 1 1 calc R U
C3 C 0.1379(7) 0.6349(4) 0.0774(4) 0.0426(11) Uani 1 1 d . .
H3 H 0.0544 0.6238 0.0128 0.051 Uiso 1 1 calc R U
C4 C 0.3111(6) 0.5850(3) 0.0987(3) 0.0339(9) Uani 1 1 d . .
H4 H 0.3460 0.5405 0.0481 0.041 Uiso 1 1 calc R U
C5 C 0.4352(5) 0.6008(3) 0.1964(3) 0.0237(8) Uani 1 1 d . .
C6 C 0.3833(6) 0.6659(3) 0.2726(3) 0.0275(8) Uani 1 1 d . .
C7 C 0.5098(6) 0.6796(3) 0.3811(3) 0.0312(9) Uani 1 1 d . .
C8 C 0.7035(7) 0.6225(3) 0.3931(4) 0.0368(10) Uani 1 1 d . .
C9 C 0.6214(6) 0.5463(3) 0.2142(3) 0.0272(8) Uani 1 1 d . .
C10 C 0.9225(7) 0.5019(4) 0.3314(4) 0.0466(12) Uani 1 1 d . .
H10A H 1.0081 0.5290 0.3917 0.070 Uiso 1 1 calc R U
H10B H 0.9863 0.5038 0.2665 0.070 Uiso 1 1 calc R U
H10C H 0.8930 0.4361 0.3477 0.070 Uiso 1 1 calc R U
C11 C 0.3971(8) 0.6434(4) 0.4779(4) 0.0486(12) Uani 1 1 d . .
H11A H 0.2725 0.6757 0.4740 0.073 Uiso 1 1 calc R U
H11B H 0.4744 0.6576 0.5468 0.073 Uiso 1 1 calc R U
H11C H 0.3762 0.5750 0.4715 0.073 Uiso 1 1 calc R U
C12 C 0.5648(7) 0.7856(3) 0.4015(4) 0.0397(11) Uani 1 1 d . .
H12A H 0.6422 0.7919 0.4729 0.048 Uiso 1 1 calc R U
H12B H 0.4458 0.8234 0.4017 0.048 Uiso 1 1 calc R U
N1 N 0.7395(5) 0.5579(2) 0.3134(3) 0.0286(7) Uani 1 1 d . .
O1 O 0.8195(6) 0.6317(3) 0.4756(3) 0.0684(13) Uani 1 1 d . .
O2 O 0.6725(5) 0.4917(3) 0.1473(3) 0.0497(9) Uani 1 1 d . .
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'
Br Br -0.2901 2.4595 '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
C2 C1 C6 120.9(4)
C2 C1 H1 119.5
C6 C1 H1 119.5
C1 C2 C3 120.3(4)
C1 C2 H2 119.8
C3 C2 H2 119.8
C4 C3 C2 119.9(4)
C4 C3 H3 120.1
C2 C3 H3 120.1
C3 C4 C5 120.0(4)
C3 C4 H4 120.0
C5 C4 H4 120.0
C6 C5 C4 120.3(4)
C6 C5 C9 122.0(3)
C4 C5 C9 117.7(4)
C5 C6 C1 118.5(4)
C5 C6 C7 121.0(4)
C1 C6 C7 120.5(4)
C6 C7 C12 111.6(3)
C6 C7 C8 114.2(3)
C12 C7 C8 106.7(4)
C6 C7 C11 110.3(4)
C12 C7 C11 108.3(4)
C8 C7 C11 105.4(4)
O1 C8 N1 120.5(4)
O1 C8 C7 119.4(4)
N1 C8 C7 120.1(3)
O2 C9 N1 119.2(4)
O2 C9 C5 123.0(4)
N1 C9 C5 117.8(3)
N1 C10 H10A 109.5
N1 C10 H10B 109.5
H10A C10 H10B 109.5
N1 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C7 C11 H11A 109.5
C7 C11 H11B 109.5
H11A C11 H11B 109.5
C7 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
C7 C12 Br1 111.7(3)
C7 C12 H12A 109.3
Br1 C12 H12A 109.3
C7 C12 H12B 109.3
Br1 C12 H12B 109.3
H12A C12 H12B 107.9
C8 N1 C9 124.5(3)
C8 N1 C10 117.8(3)
C9 N1 C10 117.5(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C12 1.945(5)
C1 C2 1.373(7)
C1 C6 1.388(6)
C1 H1 0.9300
C2 C3 1.372(8)
C2 H2 0.9300
C3 C4 1.369(7)
C3 H3 0.9300
C4 C5 1.397(5)
C4 H4 0.9300
C5 C6 1.380(5)
C5 C9 1.475(5)
C6 C7 1.506(6)
C7 C12 1.527(6)
C7 C8 1.536(6)
C7 C11 1.584(7)
C8 O1 1.212(5)
C8 N1 1.374(5)
C9 O2 1.203(5)
C9 N1 1.383(5)
C10 N1 1.467(5)
C10 H10A 0.9600
C10 H10B 0.9600
C10 H10C 0.9600
C11 H11A 0.9600
C11 H11B 0.9600
C11 H11C 0.9600
C12 H12A 0.9700
C12 H12B 0.9700
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C12 H12B O2 0.97 2.51 3.300(6) 138.2 2_655
C12 H12B O2 0.97 2.51 3.300(6) 138.2 2_655
C12 H12B O2 0.97 2.51 3.300(6) 138.2 2_655
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
C6 C1 C2 C3 1.6(8)
C1 C2 C3 C4 -2.0(8)
C2 C3 C4 C5 0.8(7)
C3 C4 C5 C6 0.8(6)
C3 C4 C5 C9 -179.0(4)
C4 C5 C6 C1 -1.1(6)
C9 C5 C6 C1 178.6(4)
C4 C5 C6 C7 176.5(4)
C9 C5 C6 C7 -3.8(6)
C2 C1 C6 C5 -0.1(7)
C2 C1 C6 C7 -177.7(4)
C5 C6 C7 C12 126.1(4)
C1 C6 C7 C12 -56.4(5)
C5 C6 C7 C8 5.0(6)
C1 C6 C7 C8 -177.5(4)
C5 C6 C7 C11 -113.5(4)
C1 C6 C7 C11 64.0(5)
C6 C7 C8 O1 177.0(5)
C12 C7 C8 O1 53.2(6)
C11 C7 C8 O1 -61.8(6)
C6 C7 C8 N1 -6.5(6)
C12 C7 C8 N1 -130.2(4)
C11 C7 C8 N1 114.7(5)
C6 C5 C9 O2 -177.4(4)
C4 C5 C9 O2 2.3(6)
C6 C5 C9 N1 3.7(6)
C4 C5 C9 N1 -176.6(4)
C6 C7 C12 Br1 -60.9(4)
C8 C7 C12 Br1 64.5(4)
C11 C7 C12 Br1 177.5(3)
O1 C8 N1 C9 -176.3(5)
C7 C8 N1 C9 7.2(7)
O1 C8 N1 C10 -0.6(7)
C7 C8 N1 C10 -177.1(4)
O2 C9 N1 C8 175.5(4)
C5 C9 N1 C8 -5.5(6)
O2 C9 N1 C10 -0.2(6)
C5 C9 N1 C10 178.7(4)
