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#$Date: 2019-11-10 06:54:16 +0200 (Sun, 10 Nov 2019) $
#$Revision: 225757 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/56/4515613.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_4515613
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 H8 Cl2 O2'
_chemical_formula_weight         255.08
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_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                   6.3191(3)
_cell_length_b                   15.8114(8)
_cell_length_c                   21.7404(11)
_cell_measurement_reflns_used    512
_cell_measurement_temperature    302(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      15
_cell_volume                     2172.17(19)
_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      302(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.0282
_diffrn_reflns_av_unetI/netI     0.0100
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            39635
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.249
_diffrn_reflns_theta_min         3.186
_exptl_absorpt_coefficient_mu    0.576
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6121
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.560
_exptl_crystal_description       block
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1966
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0389
_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)+(0.0605P)²+1.1380P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1118
_refine_ls_wR_factor_ref         0.1180
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1737
_reflns_number_total             1966
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs8b00327_si_008.cif
_cod_data_source_block           xxd230
_cod_database_code               4515613
_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   0.802
_shelx_estimated_absorpt_t_max   0.894
_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+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, 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
Cl1' Cl 0.76105(12) 0.85111(5) 0.05764(3) 0.0678(3) Uani 1 1 d . .
O1' O 0.8007(2) 0.86489(10) 0.19225(7) 0.0465(4) Uani 1 1 d . .
H1'A H 0.7755 0.8927 0.2232 0.070 Uiso 1 1 calc R U
Cl1 Cl 0.18342(11) -0.01433(4) 0.06579(3) 0.0609(2) Uani 1 1 d . .
O1 O 0.1825(2) -0.02524(10) 0.19914(7) 0.0451(4) Uani 1 1 d . .
H1A H 0.2145 -0.0533 0.2295 0.068 Uiso 1 1 calc R U
C1 C 0.3815(3) 0.02332(12) 0.11352(10) 0.0420(5) Uani 1 1 d . .
C2 C 0.5581(4) 0.06110(14) 0.08871(11) 0.0495(6) Uani 1 1 d . .
H2A H 0.5712 0.0666 0.0463 0.059 Uiso 1 1 calc R U
C3 C 0.7153(4) 0.09081(14) 0.12681(11) 0.0512(6) Uani 1 1 d . .
H3A H 0.8361 0.1156 0.1102 0.061 Uiso 1 1 calc R U
C4 C 0.6929(3) 0.08365(13) 0.18957(11) 0.0454(5) Uani 1 1 d . .
H4A H 0.7995 0.1042 0.2150 0.054 Uiso 1 1 calc R U
C5 C 0.5141(3) 0.04633(12) 0.21611(9) 0.0371(4) Uani 1 1 d . .
C6 C 0.3577(3) 0.01405(12) 0.17685(9) 0.0374(5) Uani 1 1 d . .
C1' C 0.5791(4) 0.81473(13) 0.11093(10) 0.0454(5) Uani 1 1 d . .
C2' C 0.3942(4) 0.77687(14) 0.09110(12) 0.0565(6) Uani 1 1 d . .
H2'A H 0.3681 0.7707 0.0492 0.068 Uiso 1 1 calc R U
C3' C 0.2491(4) 0.74846(15) 0.13328(12) 0.0560(6) Uani 1 1 d . .
H3'A H 0.1235 0.7238 0.1201 0.067 Uiso 1 1 calc R U
C4' C 0.2898(3) 0.75658(13) 0.19531(11) 0.0480(5) Uani 1 1 d . .
H4'A H 0.1910 0.7369 0.2236 0.058 Uiso 1 1 calc R U
C5' C 0.4763(3) 0.79378(11) 0.21655(9) 0.0385(5) Uani 1 1 d . .
C6' C 0.6209(3) 0.82503(12) 0.17340(10) 0.0386(5) 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'
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
_geom_angle_site_symmetry_3
C2 C1 C6 121.4(2) .
C2 C1 Cl1 120.05(17) .
C6 C1 Cl1 118.56(16) .
C1 C2 C3 119.9(2) .
C2 C3 C4 119.6(2) .
C3 C4 C5 121.8(2) .
C4 C5 C6 118.15(19) .
C4 C5 C5 120.4(2) 3_655
C6 C5 C5 121.3(2) 3_655
O1 C6 C1 119.27(19) .
O1 C6 C5 121.57(18) .
C1 C6 C5 119.16(18) .
C2' C1' C6' 121.0(2) .
C2' C1' Cl1' 119.80(18) .
C6' C1' Cl1' 119.19(17) .
C3' C2' C1' 119.9(2) .
C2' C3' C4' 119.9(2) .
C3' C4' C5' 121.4(2) .
C4' C5' C6' 118.57(19) .
C4' C5' C5' 119.6(2) 3_655
C6' C5' C5' 121.6(2) 3_655
O1' C6' C1' 120.36(19) .
O1' C6' C5' 120.41(18) .
C1' C6' C5' 119.23(18) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1' C1' 1.730(2) .
O1' C6' 1.362(2) .
Cl1 C1 1.731(2) .
O1 C6 1.359(2) .
C1 C2 1.376(3) .
C1 C6 1.393(3) .
C2 C3 1.376(3) .
C3 C4 1.376(3) .
C4 C5 1.399(3) .
C5 C6 1.402(3) .
C5 C5 1.484(4) 3_655
C1' C2' 1.382(3) .
C1' C6' 1.393(3) .
C2' C3' 1.372(4) .
C3' C4' 1.379(3) .
C4' C5' 1.396(3) .
C5' C6' 1.400(3) .
C5' C5' 1.485(4) 3_655
