#------------------------------------------------------------------------------
#$Date: 2019-11-10 06:54:59 +0200 (Sun, 10 Nov 2019) $
#$Revision: 225760 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/56/4515616.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_4515616
loop_
_publ_author_name
'Xiong, Xiaodong'
'Yeung, Ying-Yeung'
_publ_section_title
;
 Ammonium Salt-Catalyzed Highly Practical Ortho-Selective Monohalogenation
 and Phenylselenation of Phenols: Scope and Applications
;
_journal_issue                   5
_journal_name_full               'ACS Catalysis'
_journal_page_first              4033
_journal_paper_doi               10.1021/acscatal.8b00327
_journal_volume                  8
_journal_year                    2018
_chemical_formula_sum            'C8 H6 Br Cl O3'
_chemical_formula_weight         265.49
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 93.138(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.1058(4)
_cell_length_b                   17.9301(19)
_cell_length_c                   12.4296(15)
_cell_measurement_reflns_used    395
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      15
_cell_volume                     913.66(17)
_computing_cell_refinement       'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_data_collection       'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_data_reduction        'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_molecular_graphics    'BRUKER SHELXTL'
_computing_publication_material  'BRUKER SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'BRUKER D8VENTURE DIFFRACTOMETER'
_diffrn_measurement_method       'PHI & OMEGA SCAN'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16577
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.880
_diffrn_reflns_theta_min         2.272
_exptl_absorpt_coefficient_mu    4.759
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.2931
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.930
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.789
_refine_diff_density_min         -0.765
_refine_diff_density_rms         0.160
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.279
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         2170
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.279
_refine_ls_R_factor_all          0.0752
_refine_ls_R_factor_gt           0.0600
_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)+(0.0500P)²+5.7653P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1801
_refine_ls_wR_factor_ref         0.1859
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1742
_reflns_number_total             2170
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs8b00327_si_012.cif
_cod_data_source_block           xxd268
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4515616
_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_min   0.252
_shelx_estimated_absorpt_t_max   0.449
_shelxl_version_number           2014/6
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 0.5265(2) 0.48078(4) 0.77804(7) 0.0548(3) Uani 1 1 d . .
Cl1 Cl 0.5394(5) 0.78497(9) 0.74697(14) 0.0425(4) Uani 1 1 d . .
O1 O 0.6673(13) 0.6299(3) 0.6888(4) 0.0444(12) Uani 1 1 d . .
H1 H 0.7056 0.6711 0.6637 0.067 Uiso 1 1 calc R U
O2 O -0.0434(17) 0.7786(3) 1.0419(5) 0.0626(17) Uani 1 1 d . .
O3 O 0.2348(13) 0.8447(3) 0.9279(4) 0.0476(13) Uani 1 1 d . .
C1 C 0.5054(15) 0.6381(4) 0.7795(5) 0.0312(13) Uani 1 1 d . .
C2 C 0.4200(16) 0.5745(3) 0.8331(5) 0.0331(13) Uani 1 1 d . .
C3 C 0.2599(17) 0.5785(4) 0.9274(6) 0.0399(15) Uani 1 1 d . .
H3A H 0.2070 0.5349 0.9631 0.048 Uiso 1 1 calc R U
C4 C 0.1784(17) 0.6463(4) 0.9688(6) 0.0392(15) Uani 1 1 d . .
H4A H 0.0722 0.6483 1.0329 0.047 Uiso 1 1 calc R U
C5 C 0.2518(15) 0.7123(3) 0.9165(5) 0.0313(13) Uani 1 1 d . .
C6 C 0.4198(15) 0.7077(3) 0.8209(5) 0.0306(12) Uani 1 1 d . .
C7 C 0.1333(17) 0.7819(4) 0.9682(5) 0.0371(14) Uani 1 1 d . .
C8 C 0.110(2) 0.9126(4) 0.9748(7) 0.054(2) Uani 1 1 d . .
H8A H 0.1987 0.9552 0.9398 0.082 Uiso 1 1 calc R U
H8B H -0.1236 0.9134 0.9652 0.082 Uiso 1 1 calc R U
H8C H 0.1726 0.9141 1.0504 0.082 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
C7 O3 C8 116.1(6)
O1 C1 C6 123.4(6)
O1 C1 C2 117.7(6)
C6 C1 C2 119.0(5)
C1 C2 C3 121.0(6)
C1 C2 Br1 119.7(5)
C3 C2 Br1 119.3(5)
C4 C3 C2 120.3(6)
C3 C4 C5 121.1(6)
C4 C5 C6 118.2(6)
C4 C5 C7 115.1(5)
C6 C5 C7 126.6(6)
C1 C6 C5 120.4(6)
C1 C6 Cl1 115.4(5)
C5 C6 Cl1 124.2(5)
O2 C7 O3 123.5(6)
O2 C7 C5 120.7(6)
O3 C7 C5 115.8(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C2 1.875(6)
Cl1 C6 1.748(6)
O1 C1 1.348(7)
O2 C7 1.201(8)
O3 C7 1.309(8)
O3 C8 1.456(8)
C1 C6 1.401(8)
C1 C2 1.376(9)
C2 C3 1.377(9)
C3 C4 1.369(9)
C4 C5 1.391(9)
C5 C6 1.408(8)
C5 C7 1.496(9)
