#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:36:20 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180345 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/14/7201403.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_7201403
loop_
_publ_author_name
'Gajda, Roman'
'Katrusiak, Andrzej'
'Crassous, Jeanne'
_publ_section_title
;
 Pressure-controlled aggregation in carboxylic acids. A case study on
 the polymorphism of bromochlorofluoroacetic acid
;
_journal_issue                   12
_journal_name_full               CrystEngComm
_journal_page_first              2668
_journal_paper_doi               10.1039/b910409g
_journal_volume                  11
_journal_year                    2009
_chemical_formula_moiety         'C2 H Br Cl F O2'
_chemical_formula_sum            'C2 H Br Cl F O2'
_chemical_formula_weight         191.39
_chemical_name_common            'bromochlorofluorocarboxylic acid'
_chemical_name_systematic
;
bromochlorofluorocarboxylic acid
;
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   16.169(4)
_cell_length_b                   6.0038(16)
_cell_length_c                   20.971(4)
_cell_measurement_reflns_used    3964
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.97
_cell_measurement_theta_min      3.62
_cell_volume                     2035.8(8)
_computing_cell_refinement       'CrysAlis (Oxford Diffraction, 2004)'
_computing_data_collection       'CrysAlis (Oxford Diffraction, 2004)'
_computing_data_reduction        'CrysAlis (Oxford Diffraction, 2004)'
_computing_molecular_graphics    'X-seed 2.0'
_computing_publication_material  'X-seed 2.0'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_pressure         590000
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.396
_diffrn_measured_fraction_theta_max 0.396
_diffrn_measurement_device_type  'Kuma KM4CCD κ geometry'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0693
_diffrn_reflns_av_sigmaI/netI    0.0299
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            7980
_diffrn_reflns_theta_full        24.97
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_min         3.62
_exptl_absorpt_coefficient_mu    8.503
_exptl_absorpt_correction_T_max  0.49
_exptl_absorpt_correction_T_min  0.32
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
Katrusiak, A. (2003). REDSHADE - Program for correcting
reflections intensities for DAC absorption, gasket shadowing
and sample crystal absorption. Adam Mickiewicz University, Poznań.

Katrusiak, A. (2004). Z. Kristallogr. 219, 461-467
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.498
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       disc
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.470
_exptl_crystal_size_mid          0.460
_exptl_crystal_size_min          0.085
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     122
_refine_ls_number_reflns         706
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0694
_refine_ls_R_factor_gt           0.0616
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0789P)²+20.2760P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1475
_refine_ls_wR_factor_ref         0.1530
_reflns_number_gt                628
_reflns_number_total             706
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b910409g.txt
_cod_data_source_block           bromochlorofluorocarboxylic_acid_2
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_cell_volume        2035.7(9)
_cod_original_sg_symbol_H-M      'P bcn'
_cod_database_code               7201403
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.1474(12) -1.041(4) 0.7427(6) 0.047(5) Uani 1 1 d . . .
C2 C 1.1083(11) -0.963(3) 0.6818(6) 0.048(5) Uani 1 1 d . . .
O1 O 1.2118(10) -0.928(3) 0.7591(4) 0.065(5) Uani 1 1 d . . .
H1 H 1.2299 -0.9755 0.7929 0.097 Uiso 1 1 calc R . .
O2 O 1.1176(8) -1.196(2) 0.7701(4) 0.057(3) Uani 1 1 d . . .
Br1 Br 1.1807(2) -1.0096(6) 0.61609(9) 0.0703(10) Uani 0.34 1 d P . .
Br2 Br 1.08107(17) -0.6642(5) 0.68700(9) 0.0793(10) Uani 0.66 1 d P . .
Cl1 Cl 1.1807(2) -1.0096(6) 0.61609(9) 0.0703(10) Uani 0.66 1 d P . .
Cl2 Cl 1.08107(17) -0.6642(5) 0.68700(9) 0.0793(10) Uani 0.34 1 d P . .
F1 F 1.0430(9) -1.084(3) 0.6687(5) 0.108(6) Uani 1 1 d . . .
C3 C 1.3370(11) -1.037(3) 0.8960(6) 0.038(4) Uiso 1 1 d . . .
C4 C 1.3512(9) -1.164(3) 0.9601(5) 0.034(4) Uani 1 1 d . . .
O3 O 1.3973(7) -0.909(2) 0.8827(4) 0.054(3) Uani 1 1 d . . .
H3 H 1.3875 -0.8420 0.8495 0.082 Uiso 1 1 calc R . .
O4 O 1.2749(7) -1.0768(17) 0.8667(3) 0.050(3) Uani 1 1 d . . .
Br3 Br 1.42121(15) -1.4000(4) 0.94485(8) 0.0565(8) Uani 0.68 1 d P . .
Br4 Br 1.39044(16) -0.9837(5) 1.02307(9) 0.0474(8) Uani 0.32 1 d P . .
Cl3 Cl 1.42121(15) -1.4000(4) 0.94485(8) 0.0565(8) Uani 0.32 1 d P . .
Cl4 Cl 1.39044(16) -0.9837(5) 1.02307(9) 0.0474(8) Uani 0.68 1 d P . .
F2 F 1.2776(5) -1.2437(15) 0.9793(3) 0.049(3) 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'
F F 0.0171 0.0103 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 C1 O1 127.5(16) . . ?
O2 C1 C2 118.9(14) . . ?
O1 C1 C2 113.6(15) . . ?
F1 C2 C1 110.1(12) . . ?
F1 C2 Br1 105.8(13) . . ?
C1 C2 Br1 108.9(14) . . ?
F1 C2 Cl1 105.8(13) . . ?
C1 C2 Cl1 108.9(14) . . ?
Br1 C2 Cl1 0.0(2) . . ?
F1 C2 Br2 111.1(18) . . ?
C1 C2 Br2 110.7(12) . . ?
Br1 C2 Br2 110.2(7) . . ?
Cl1 C2 Br2 110.2(7) . . ?
F1 C2 Cl2 111.1(18) . . ?
C1 C2 Cl2 110.7(12) . . ?
Br1 C2 Cl2 110.2(7) . . ?
Cl1 C2 Cl2 110.2(7) . . ?
Br2 C2 Cl2 0.0(2) . . ?
O4 C3 O3 130.4(16) . . ?
O4 C3 C4 117.9(13) . . ?
O3 C3 C4 111.7(15) . . ?
F2 C4 C3 107.5(11) . . ?
F2 C4 Cl4 107.6(7) . . ?
C3 C4 Cl4 112.7(12) . . ?
F2 C4 Br4 107.6(7) . . ?
C3 C4 Br4 112.7(12) . . ?
Cl4 C4 Br4 0.00(8) . . ?
F2 C4 Br3 108.8(12) . . ?
C3 C4 Br3 108.4(10) . . ?
Cl4 C4 Br3 111.7(8) . . ?
Br4 C4 Br3 111.7(8) . . ?
F2 C4 Cl3 108.8(12) . . ?
C3 C4 Cl3 108.4(10) . . ?
Cl4 C4 Cl3 111.7(8) . . ?
Br4 C4 Cl3 111.7(8) . . ?
Br3 C4 Cl3 0.00(15) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O2 1.193(19) . ?
C1 O1 1.291(19) . ?
C1 C2 1.50(2) . ?
C2 F1 1.311(17) . ?
C2 Br1 1.829(17) . ?
C2 Cl1 1.829(17) . ?
C2 Br2 1.85(2) . ?
C2 Cl2 1.85(2) . ?
C3 O4 1.200(17) . ?
C3 O3 1.274(18) . ?
C3 C4 1.56(2) . ?
C4 F2 1.345(16) . ?
C4 Cl4 1.822(15) . ?
C4 Br4 1.822(15) . ?
C4 Br3 1.841(16) . ?
C4 Cl3 1.841(16) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C1 C2 F1 1(3) . . . . ?
O1 C1 C2 F1 -179(2) . . . . ?
O2 C1 C2 Br1 -115(2) . . . . ?
O1 C1 C2 Br1 65(2) . . . . ?
O2 C1 C2 Cl1 -115(2) . . . . ?
O1 C1 C2 Cl1 65(2) . . . . ?
O2 C1 C2 Br2 124(2) . . . . ?
O1 C1 C2 Br2 -56(2) . . . . ?
O2 C1 C2 Cl2 124(2) . . . . ?
O1 C1 C2 Cl2 -56(2) . . . . ?
O4 C3 C4 F2 -19(2) . . . . ?
O3 C3 C4 F2 163.0(16) . . . . ?
O4 C3 C4 Cl4 -137.2(14) . . . . ?
O3 C3 C4 Cl4 45(2) . . . . ?
O4 C3 C4 Br4 -137.2(14) . . . . ?
O3 C3 C4 Br4 45(2) . . . . ?
O4 C3 C4 Br3 98.6(17) . . . . ?
O3 C3 C4 Br3 -79.5(19) . . . . ?
O4 C3 C4 Cl3 98.6(17) . . . . ?
O3 C3 C4 Cl3 -79.5(19) . . . . ?
