#------------------------------------------------------------------------------
#$Date: 2019-11-10 06:55:26 +0200 (Sun, 10 Nov 2019) $
#$Revision: 225762 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/56/4515618.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_4515618
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            'C7 H4 Br Cl O2'
_chemical_formula_weight         235.46
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 101.499(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.7896(3)
_cell_length_b                   13.5178(6)
_cell_length_c                   15.0171(6)
_cell_measurement_reflns_used    124
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      15
_cell_volume                     1549.54(11)
_computing_cell_refinement       'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_data_collection       'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_data_reduction        'BRUKER KAPPA APEXII DUO 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 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_diffrn_measurement_method       'PHI & OMEGA SCAN'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12270
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.249
_diffrn_reflns_theta_min         2.046
_exptl_absorpt_coefficient_mu    5.589
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4653
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.019
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.623
_refine_diff_density_min         -0.681
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         2805
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0330
_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)+(0.0524P)²+1.1609P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0887
_refine_ls_wR_factor_ref         0.0983
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2214
_reflns_number_total             2805
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs8b00327_si_013.cif
_cod_data_source_block           xxd271
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4515618
_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   0.167
_shelx_estimated_absorpt_t_max   0.285
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
Br1' Br 0.12459(6) 0.10224(3) 0.07083(3) 0.05117(17) Uani 1 1 d . .
Cl1' Cl 0.44069(14) 0.34852(8) 0.34521(6) 0.0434(3) Uani 1 1 d . .
Br1 Br 0.98714(7) 0.42119(4) 0.40828(3) 0.05938(18) Uani 1 1 d . .
Cl1 Cl 0.70814(13) 0.15607(7) 0.14406(6) 0.0422(3) Uani 1 1 d . .
C1 C 0.9340(5) 0.3856(3) 0.2848(2) 0.0362(9) Uani 1 1 d . .
C2 C 0.8603(5) 0.2932(3) 0.2626(2) 0.0341(9) Uani 1 1 d . .
C3 C 0.8122(5) 0.2697(3) 0.1710(2) 0.0333(8) Uani 1 1 d . .
C4 C 0.8457(5) 0.3349(3) 0.1030(2) 0.0345(8) Uani 1 1 d . .
C5 C 0.9260(5) 0.4245(3) 0.1291(3) 0.0412(9) Uani 1 1 d . .
H5A H 0.9515 0.4673 0.0850 0.049 Uiso 1 1 calc R U
C6 C 0.9689(5) 0.4513(3) 0.2197(3) 0.0401(9) Uani 1 1 d . .
H6A H 1.0203 0.5124 0.2367 0.048 Uiso 1 1 calc R U
C7 C 0.7991(5) 0.3081(4) 0.0056(3) 0.0471(11) Uani 1 1 d . .
H7A H 0.7352 0.2506 -0.0107 0.057 Uiso 1 1 calc R U
O1' O 0.2507(4) 0.1695(2) 0.2595(2) 0.0448(8) Uani 1 1 d . .
O2' O 0.5548(4) 0.5459(2) 0.1444(2) 0.0545(8) Uani 1 1 d . .
C1' C 0.2426(5) 0.2214(3) 0.1094(2) 0.0338(8) Uani 1 1 d . .
C2' C 0.2907(5) 0.2391(3) 0.2024(2) 0.0323(8) Uani 1 1 d . .
C3' C 0.3770(4) 0.3270(3) 0.2290(2) 0.0325(8) Uani 1 1 d . .
C4' C 0.4151(5) 0.3956(3) 0.1658(2) 0.0342(8) Uani 1 1 d . .
C5' C 0.3649(5) 0.3739(3) 0.0736(3) 0.0380(9) Uani 1 1 d . .
H5'A H 0.3900 0.4185 0.0308 0.046 Uiso 1 1 calc R U
C6' C 0.2784(5) 0.2872(3) 0.0452(2) 0.0384(9) Uani 1 1 d . .
H6'A H 0.2444 0.2732 -0.0164 0.046 Uiso 1 1 calc R U
C7' C 0.5056(5) 0.4894(3) 0.1945(3) 0.0437(10) Uani 1 1 d . .
H7'A H 0.5255 0.5055 0.2560 0.052 Uiso 1 1 calc R U
O1 O 0.8315(5) 0.2336(3) 0.3299(2) 0.0533(9) Uani 1 1 d . .
O2 O 0.8402(5) 0.3573(3) -0.05317(19) 0.0601(9) Uani 1 1 d . .
H1A H 0.841(5) 0.184(3) 0.318(3) 0.038(14) Uiso 1 1 d . .
H1A' H 0.267(6) 0.181(4) 0.307(3) 0.054(15) Uiso 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'
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
C2 C1 C6 122.5(3)
C2 C1 Br1 117.8(3)
C6 C1 Br1 119.7(3)
O1 C2 C1 118.7(3)
O1 C2 C3 123.7(4)
C1 C2 C3 117.5(3)
C2 C3 C4 121.4(4)
C2 C3 Cl1 116.9(3)
C4 C3 Cl1 121.7(3)
C5 C4 C3 118.7(3)
C5 C4 C7 120.0(4)
C3 C4 C7 121.2(4)
C6 C5 C4 121.0(4)
C5 C6 C1 118.8(4)
O2 C7 C4 123.0(4)
C6' C1' C2' 122.5(4)
C6' C1' Br1' 119.3(3)
C2' C1' Br1' 118.2(3)
O1' C2' C3' 125.1(3)
O1' C2' C1' 117.8(3)
C3' C2' C1' 117.1(3)
C2' C3' C4' 122.0(3)
C2' C3' Cl1' 117.2(3)
C4' C3' Cl1' 120.8(3)
C5' C4' C3' 118.6(4)
C5' C4' C7' 119.7(4)
C3' C4' C7' 121.7(3)
C6' C5' C4' 120.7(4)
C5' C6' C1' 119.2(3)
O2' C7' C4' 124.3(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1' C1' 1.887(4)
Cl1' C3' 1.741(3)
Br1 C1 1.881(4)
Cl1 C3 1.746(4)
C1 C2 1.387(6)
C1 C6 1.388(6)
C2 O1 1.346(5)
C2 C3 1.388(5)
C3 C4 1.411(5)
C4 C5 1.384(6)
C4 C7 1.480(5)
C5 C6 1.383(5)
C7 O2 1.198(5)
O1' C2' 1.351(4)
O2' C7' 1.188(5)
C1' C6' 1.381(5)
C1' C2' 1.393(5)
C2' C3' 1.384(5)
C3' C4' 1.401(5)
C4' C5' 1.392(5)
C4' C7' 1.473(6)
C5' C6' 1.376(6)
