#------------------------------------------------------------------------------
#$Date: 2019-11-10 06:56:10 +0200 (Sun, 10 Nov 2019) $
#$Revision: 225765 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/56/4515621.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_4515621
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            'C12 H16 B Cl O3'
_chemical_formula_weight         254.51
_space_group_crystal_system      tetragonal
_space_group_IT_number           82
_space_group_name_Hall           'I -4'
_space_group_name_H-M_alt        'I -4'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.7094(9)
_cell_length_b                   19.7094(9)
_cell_length_c                   6.8557(3)
_cell_measurement_reflns_used    233
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      15
_cell_volume                     2663.2(2)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0385
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            22426
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.248
_diffrn_reflns_theta_min         2.923
_exptl_absorpt_coefficient_mu    0.279
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6124
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_description       block
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.39(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2426
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0519
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0735P)²+2.8872P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1317
_refine_ls_wR_factor_ref         0.1392
_reflns_Friedel_coverage         0.834
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2142
_reflns_number_total             2426
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs8b00327_si_004.cif
_cod_data_source_block           XXD267
_cod_original_cell_volume        2663.2(3)
_cod_database_code               4515621
_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   0.896
_shelx_estimated_absorpt_t_max   0.946
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'y, -x, -z'
'-y, x, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'y+1/2, -x+1/2, -z+1/2'
'-y+1/2, x+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
Cl1 Cl 0.80041(7) 0.58269(7) 0.3027(2) 0.0660(4) Uani 1 1 d . . . . .
B1 B 0.7233(2) 0.5790(3) 0.7141(9) 0.0417(11) Uani 1 1 d . . . . .
O1 O 0.90375(16) 0.48251(16) 0.2846(6) 0.0553(9) Uani 1 1 d . . . . .
H1A H 0.9361 0.4564 0.2875 0.083 Uiso 1 1 calc R U . . .
O2 O 0.7022(4) 0.6313(3) 0.6172(9) 0.157(4) Uani 1 1 d . . . . .
O3 O 0.6860(3) 0.5705(3) 0.8702(10) 0.143(3) Uani 1 1 d . . . . .
C1 C 0.8182(2) 0.52677(19) 0.4909(7) 0.0374(9) Uani 1 1 d . . . . .
C2 C 0.8705(2) 0.4805(2) 0.4602(7) 0.0410(10) Uani 1 1 d . . . . .
C3 C 0.8859(2) 0.4345(2) 0.6036(8) 0.0505(12) Uani 1 1 d . . . . .
H3A H 0.9201 0.4028 0.5833 0.061 Uiso 1 1 calc R U . . .
C4 C 0.8510(2) 0.4351(3) 0.7774(9) 0.0569(13) Uani 1 1 d . . . . .
H4A H 0.8619 0.4042 0.8750 0.068 Uiso 1 1 calc R U . . .
C5 C 0.7996(2) 0.4819(2) 0.8065(8) 0.0487(10) Uani 1 1 d . . . . .
H5A H 0.7763 0.4820 0.9244 0.058 Uiso 1 1 calc R U . . .
C6 C 0.7822(2) 0.5287(2) 0.6632(7) 0.0395(10) Uani 1 1 d . . . . .
C7 C 0.6646(7) 0.6750(6) 0.770(2) 0.063(6) Uani 0.43(2) 1 d D . P A 1
C8 C 0.6198(14) 0.718(2) 0.632(4) 0.15(2) Uani 0.43(2) 1 d D . P A 1
H8A H 0.6449 0.7567 0.5879 0.231 Uiso 0.43(2) 1 calc R U P A 1
H8B H 0.6068 0.6908 0.5213 0.231 Uiso 0.43(2) 1 calc R U P A 1
H8C H 0.5799 0.7325 0.7001 0.231 Uiso 0.43(2) 1 calc R U P A 1
C9 C 0.7046(14) 0.7077(10) 0.938(4) 0.090(8) Uani 0.43(2) 1 d D . P A 1
H9A H 0.7296 0.7460 0.8900 0.135 Uiso 0.43(2) 1 calc R U P A 1
H9B H 0.6736 0.7225 1.0377 0.135 Uiso 0.43(2) 1 calc R U P A 1
H9C H 0.7355 0.6751 0.9923 0.135 Uiso 0.43(2) 1 calc R U P A 1
C10 C 0.6235(8) 0.6135(7) 0.837(3) 0.078(8) Uani 0.43(2) 1 d D . P A 1
C11 C 0.5972(17) 0.6215(18) 1.047(3) 0.090(9) Uani 0.43(2) 1 d D . P A 1
H11A H 0.5566 0.6485 1.0467 0.135 Uiso 0.43(2) 1 calc R U P A 1
H11B H 0.5874 0.5776 1.1010 0.135 Uiso 0.43(2) 1 calc R U P A 1
H11C H 0.6312 0.6435 1.1253 0.135 Uiso 0.43(2) 1 calc R U P A 1
C12 C 0.5708(11) 0.591(3) 0.685(6) 0.16(2) Uani 0.43(2) 1 d D . P A 1
H12A H 0.5343 0.6233 0.6811 0.247 Uiso 0.43(2) 1 calc R U P A 1
H12B H 0.5919 0.5885 0.5590 0.247 Uiso 0.43(2) 1 calc R U P A 1
H12C H 0.5532 0.5472 0.7199 0.247 Uiso 0.43(2) 1 calc R U P A 1
C7' C 0.6322(6) 0.6505(7) 0.6952(17) 0.068(4) Uani 0.57(2) 1 d D . P A 2
C8' C 0.6282(14) 0.7268(9) 0.645(4) 0.117(10) Uani 0.57(2) 1 d D . P A 2
H8'A H 0.5855 0.7447 0.6878 0.176 Uiso 0.57(2) 1 calc R U P A 2
H8'B H 0.6645 0.7504 0.7088 0.176 Uiso 0.57(2) 1 calc R U P A 2
H8'C H 0.6323 0.7326 0.5062 0.176 Uiso 0.57(2) 1 calc R U P A 2
C9' C 0.5675(14) 0.611(2) 0.644(6) 0.19(2) Uani 0.57(2) 1 d D . P A 2
H9'A H 0.5292 0.6311 0.7076 0.281 Uiso 0.57(2) 1 calc R U P A 2
H9'B H 0.5606 0.6117 0.5051 0.281 Uiso 0.57(2) 1 calc R U P A 2
H9'C H 0.5721 0.5646 0.6864 0.281 Uiso 0.57(2) 1 calc R U P A 2
C10' C 0.6521(8) 0.6393(9) 0.9085(18) 0.081(6) Uani 0.57(2) 1 d D . P A 2
C11' C 0.594(2) 0.6122(19) 1.035(7) 0.24(3) Uani 0.57(2) 1 d D . P A 2
H11D H 0.6091 0.6062 1.1662 0.362 Uiso 0.57(2) 1 calc R U P A 2
H11E H 0.5567 0.6439 1.0327 0.362 Uiso 0.57(2) 1 calc R U P A 2
H11F H 0.5785 0.5694 0.9836 0.362 Uiso 0.57(2) 1 calc R U P A 2
C12' C 0.6853(14) 0.7025(16) 0.999(6) 0.19(2) Uani 0.57(2) 1 d D . P A 2
H12D H 0.6970 0.6933 1.1323 0.291 Uiso 0.57(2) 1 calc R U P A 2
H12E H 0.7256 0.7137 0.9272 0.291 Uiso 0.57(2) 1 calc R U P A 2
H12F H 0.6541 0.7399 0.9936 0.291 Uiso 0.57(2) 1 calc R U P A 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'
B B 0.0013 0.0007 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O2 B1 O3 109.9(5)
O2 B1 C6 129.0(5)
O3 B1 C6 121.1(5)
B1 O2 C7' 108.0(6)
B1 O2 C7 104.5(7)
B1 O3 C10 105.3(7)
B1 O3 C10' 105.7(7)
C6 C1 C2 121.9(4)
C6 C1 Cl1 121.2(3)
C2 C1 Cl1 117.0(3)
O1 C2 C3 122.8(4)
O1 C2 C1 117.9(4)
C3 C2 C1 119.3(4)
C2 C3 C4 120.2(4)
C3 C4 C5 119.8(5)
C4 C5 C6 121.4(5)
C1 C6 C5 117.4(4)
C1 C6 B1 126.1(4)
C5 C6 B1 116.5(4)
C10 C7 C9 112.1(18)
C10 C7 O2 91.0(10)
C9 C7 O2 119.7(13)
C10 C7 C8 108(2)
C9 C7 C8 122(2)
O2 C7 C8 99.4(14)
O3 C10 C7 93.3(10)
O3 C10 C12 119(2)
C7 C10 C12 112(2)
O3 C10 C11 101(2)
C7 C10 C11 112.3(18)
C12 C10 C11 116(2)
O2 C7' C10' 93.9(9)
O2 C7' C9' 122.9(17)
C10' C7' C9' 111(2)
O2 C7' C8' 102.0(14)
C10' C7' C8' 111.5(16)
C9' C7' C8' 114(2)
C7' C10' O3 94.3(9)
C7' C10' C11' 113(2)
O3 C10' C11' 96.6(18)
C7' C10' C12' 112(2)
O3 C10' C12' 126.8(17)
C11' C10' C12' 112(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C1 1.732(4)
B1 O2 1.295(7)
B1 O3 1.310(7)
B1 C6 1.566(6)
O1 C2 1.371(6)
O2 C7' 1.527(12)
O2 C7 1.544(14)
O3 C10 1.513(17)
O3 C10' 1.534(14)
C1 C6 1.379(6)
C1 C2 1.393(6)
C2 C3 1.372(7)
C3 C4 1.376(7)
C4 C5 1.383(7)
C5 C6 1.390(6)
C7 C10 1.529(13)
C7 C9 1.540(14)
C7 C8 1.545(14)
C10 C12 1.538(14)
C10 C11 1.538(13)
C7' C10' 1.530(12)
C7' C9' 1.538(14)
C7' C8' 1.545(13)
C10' C11' 1.537(14)
C10' C12' 1.537(14)
