#------------------------------------------------------------------------------
#$Date: 2019-11-10 06:54:30 +0200 (Sun, 10 Nov 2019) $
#$Revision: 225758 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/56/4515614.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_4515614
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 H7 Cl O2'
_chemical_formula_weight         170.59
_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   mixed
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 108.0691(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.7838(3)
_cell_length_b                   16.4432(8)
_cell_length_c                   7.2539(3)
_cell_measurement_reflns_used    323
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      15
_cell_volume                     769.25(6)
_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 0.988
_diffrn_measured_fraction_theta_max 0.988
_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  0.0191
_diffrn_reflns_av_unetI/netI     0.0102
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            13159
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.236
_diffrn_reflns_theta_min         2.477
_exptl_absorpt_coefficient_mu    0.436
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6550
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.400
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.111
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     104
_refine_ls_number_reflns         1375
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.129
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0376
_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)+(0.0768P)²+0.2732P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1228
_refine_ls_wR_factor_ref         0.1263
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1277
_reflns_number_total             1375
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs8b00327_si_003.cif
_cod_data_source_block           XXD287
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4515614
_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   0.845
_shelx_estimated_absorpt_t_max   0.918
_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
Cl1 Cl 0.16355(8) 0.66522(4) 0.83634(7) 0.0550(3) Uani 1 1 d . .
C1 C 0.0253(3) 0.62678(10) 0.9819(2) 0.0304(4) Uani 1 1 d . .
C2 C 0.1352(3) 0.60827(11) 1.1741(3) 0.0346(4) Uani 1 1 d . .
C3 C 0.0293(3) 0.57612(11) 1.2928(3) 0.0401(5) Uani 1 1 d . .
H3A H 0.1001 0.5650 1.4221 0.048 Uiso 1 1 calc R U
C4 C -0.1800(3) 0.56047(12) 1.2207(3) 0.0400(5) Uani 1 1 d . .
H4A H -0.2494 0.5387 1.3015 0.048 Uiso 1 1 calc R U
C5 C -0.2874(3) 0.57681(11) 1.0292(3) 0.0348(4) Uani 1 1 d . .
H5A H -0.4281 0.5649 0.9808 0.042 Uiso 1 1 calc R U
C6 C -0.1863(3) 0.61094(10) 0.9086(2) 0.0283(4) Uani 1 1 d . .
C7 C -0.3174(3) 0.63070(11) 0.7058(2) 0.0329(4) Uani 1 1 d . .
C8 C -0.3083(4) 0.71263(14) 0.6221(3) 0.0588(7) Uani 1 1 d . .
H8A H -0.2026 0.7444 0.7119 0.088 Uiso 1 1 calc R U
H8B H -0.2766 0.7072 0.5026 0.088 Uiso 1 1 calc R U
H8C H -0.4399 0.7392 0.5979 0.088 Uiso 1 1 calc R U
O1 O 0.3413(2) 0.62282(12) 1.2354(2) 0.0548(5) Uani 1 1 d . .
O2 O -0.4412(3) 0.58043(9) 0.6159(2) 0.0554(5) Uani 1 1 d . .
H1A H 0.387(5) 0.6060(18) 1.344(5) 0.077(9) 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C6 C1 C2 120.59(16)
C6 C1 Cl1 121.59(13)
C2 C1 Cl1 117.74(14)
O1 C2 C3 123.10(17)
O1 C2 C1 117.92(17)
C3 C2 C1 118.98(17)
C4 C3 C2 120.51(17)
C3 C4 C5 120.44(17)
C4 C5 C6 120.22(17)
C5 C6 C1 119.22(16)
C5 C6 C7 116.56(16)
C1 C6 C7 124.19(16)
O2 C7 C8 120.48(17)
O2 C7 C6 118.72(16)
C8 C7 C6 120.62(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C1 1.7345(17)
C1 C6 1.392(2)
C1 C2 1.396(2)
C2 O1 1.351(2)
C2 C3 1.386(3)
C3 C4 1.376(3)
C4 C5 1.380(3)
C5 C6 1.387(3)
C6 C7 1.500(2)
C7 O2 1.214(2)
C7 C8 1.487(3)
