#------------------------------------------------------------------------------
#$Date: 2017-04-22 05:22:27 +0300 (Sat, 22 Apr 2017) $
#$Revision: 195684 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/57/1545790.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_1545790
loop_
_publ_author_name
'Pramanik, Titas'
'Srinivas, Pavan Mysore'
'Tayur, Guru Row N.'
_publ_section_title
;
 FDHALO17: Do halogen bonds dictate the packing preferences in solid
 solutions?
;
_journal_name_full               'Faraday Discuss.'
_journal_paper_doi               10.1039/C7FD00084G
_journal_year                    2017
_chemical_formula_moiety         'C7 H4 Br Cl O2'
_chemical_formula_sum            'C7 H4 Br Cl O2'
_chemical_formula_weight         235.46
_chemical_name_systematic
'4-bromo-2-chlobenzoic acid/ 2-bromo-4-chlorobenzoic acid'
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2017-04-18 deposited with the CCDC.
2017-04-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.036(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.2399(3)
_cell_length_b                   9.0087(2)
_cell_length_c                   12.0539(4)
_cell_measurement_reflns_used    3289
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.6800
_cell_measurement_theta_min      2.8680
_cell_volume                     759.26(5)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.870
_diffrn_measurement_device_type  'Xcalibur, Eos, Nova'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.870
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5835
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.870
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.408
_diffrn_reflns_theta_min         2.859
_exptl_absorpt_coefficient_mu    5.703
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    2.060
_exptl_crystal_description       Block
_exptl_crystal_F_000             456
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: methanol'
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.579
_refine_diff_density_rms         0.093
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     107
_refine_ls_number_reflns         2007
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0277
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0282P)²+0.3256P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0641
_refine_ls_wR_factor_ref         0.0667
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1791
_reflns_number_total             2007
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7fd00084g2.cif
_cod_data_source_block           shelx
_cod_database_code               1545790
_shelx_shelxl_version_number     2016/6
_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.
;
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.8842(4) 0.3789(4) 0.24397(12) 0.0201(2) Uani 0.6151(13) 1 d D . P A 1
Cl1 Cl 0.5793(12) 0.8164(5) -0.0552(10) 0.0195(4) Uani 0.6151(13) 1 d D . P A 1
Cl2 Cl 0.8911(19) 0.3812(15) 0.2314(5) 0.0201(2) Uani 0.3849(13) 1 d D . P A 2
Br2 Br 0.5881(7) 0.8387(3) -0.0550(6) 0.0195(4) Uani 0.3849(13) 1 d D . P A 2
O1 O 0.9151(2) 0.13848(17) -0.08990(13) 0.0244(4) Uani 1 1 d . . . . .
O2 O 0.9398(3) 0.13034(17) 0.09788(14) 0.0268(4) Uani 1 1 d . . . . .
H2 H 0.980465 0.046998 0.090405 0.040 Uiso 1 1 calc R U . . .
C1 C 0.8956(3) 0.1965(2) -0.00029(18) 0.0151(4) Uani 1 1 d . . . . .
C5 C 0.6754(3) 0.6398(2) -0.0355(2) 0.0174(4) Uani 1 1 d D . . . .
C2 C 0.8180(3) 0.3512(2) -0.00493(18) 0.0146(4) Uani 1 1 d . . . . .
C3 C 0.8077(3) 0.4390(2) 0.08912(16) 0.0154(4) Uani 1 1 d D . . . .
C6 C 0.6802(3) 0.5567(2) -0.13137(19) 0.0184(4) Uani 1 1 d . . . . .
H6 H 0.636494 0.595822 -0.204942 0.022 Uiso 1 1 calc R U . . .
C4 C 0.7379(3) 0.5837(2) 0.07440(19) 0.0169(4) Uani 1 1 d . . . . .
H4 H 0.733492 0.641589 0.137566 0.020 Uiso 1 1 calc R U . . .
C7 C 0.7521(3) 0.4137(2) -0.11431(18) 0.0175(4) Uani 1 1 d . . . . .
H7 H 0.756729 0.357059 -0.178029 0.021 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
O1 C1 O2 123.17(19)
O1 C1 C2 119.06(18)
O2 C1 C2 117.77(18)
C4 C5 C6 122.05(18)
C4 C5 Cl1 119.3(4)
C6 C5 Cl1 118.6(4)
C4 C5 Br2 118.8(3)
C6 C5 Br2 119.1(3)
C7 C2 C3 117.29(18)
C7 C2 C1 116.28(18)
C3 C2 C1 126.42(19)
C4 C3 C2 121.31(18)
C4 C3 Cl2 115.3(5)
C2 C3 Cl2 123.3(5)
C4 C3 Br1 113.52(18)
C2 C3 Br1 125.16(18)
C5 C6 C7 117.94(19)
C5 C4 C3 118.86(19)
C6 C7 C2 122.5(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C3 1.884(2)
Cl1 C5 1.728(4)
Cl2 C3 1.743(5)
Br2 C5 1.895(3)
O1 C1 1.241(2)
O2 C1 1.289(3)
C1 C2 1.498(3)
C5 C4 1.380(3)
C5 C6 1.385(3)
C2 C7 1.399(3)
C2 C3 1.400(3)
C3 C4 1.393(3)
C6 C7 1.385(3)
