# Electronic Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2009

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350
loop_
_publ_author_name
_publ_author_address
'Andrzej Katrusiak'
;
Faculty of Chemistry
Adam Mickiewicz University
Grunwaldzka 6
60-780 Poznań
Poland
;
'Jeanne Crassous'
;
Faculty of Chemistry
Adam Mickiewicz University
Grunwaldzka 6
60-780 Poznań
Poland
;
'Roman Gajda' ''

_publ_contact_author_name        'Andrzej Katrusiak'
_publ_contact_author_email       KATRAN@AMU.EDU.PL

_publ_section_title              
;
Pressure-controlled aggregation in carboxylic-acids
;
_publ_contact_author_address     
;
Andrzej Katrusiak
Faculty of Chemistry
Adam Mickiewicz University
Grunwaldzka 6
60-780 Poznań
Poland
;
_publ_contact_author_fax         +48(61)8291505
_publ_contact_author_phone       +48(61)8291443

# Attachment 'brclf_acid.cif'

data_bromochlorofluorocarboxylic_acid_1
_database_code_depnum_ccdc_archive 'CCDC 723999'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
bromochlorofluorocarboxylic acid
;
_chemical_name_common            'bromochlorofluorocarboxylic acid'
_chemical_melting_point          ?
_chemical_formula_moiety         'C2 H Br Cl F O2'
_chemical_formula_sum            'C2 H Br Cl F O2'
_chemical_formula_weight         191.39

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P bcn'

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'

_cell_length_a                   16.458(5)
_cell_length_b                   6.0708(4)
_cell_length_c                   21.0950(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2107.7(6)
_cell_formula_units_Z            16
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3367
_cell_measurement_theta_min      3.58
_cell_measurement_theta_max      25.00

_exptl_crystal_description       disc
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.085
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.413
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1440
_exptl_absorpt_coefficient_mu    8.212
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.33
_exptl_absorpt_correction_T_max  0.488
_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_special_details           
;
High-pressure measurement at 0.28 GPa.
;

_diffrn_ambient_temperature      293(2)
_diffrn_ambient_pressure         280000
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Kuma KM4CCD κ geometry'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6686
_diffrn_reflns_av_R_equivalents  0.0564
_diffrn_reflns_av_sigmaI/netI    0.0255
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.58
_diffrn_reflns_theta_max         25.00
_reflns_number_total             481
_reflns_number_gt                413
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis (Oxford Diffraction, 2004)'
_computing_cell_refinement       'CrysAlis (Oxford Diffraction, 2004)'
_computing_data_reduction        'CrysAlis (Oxford Diffraction, 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'X-seed 2.0'
_computing_publication_material  'X-seed 2.0'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0861P)²+12.5069P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         481
_refine_ls_number_parameters     92
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0684
_refine_ls_wR_factor_ref         0.1696
_refine_ls_wR_factor_gt          0.1611
_refine_ls_goodness_of_fit_ref   1.204
_refine_ls_restrained_S_all      1.204
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 1.157(4) -1.039(2) 0.7428(7) 0.034(4) Uiso 1 1 d . . .
C2 C 1.093(4) -0.961(3) 0.6850(7) 0.09(6) Uani 1 1 d . . .
O1 O 1.214(2) -0.9284(19) 0.7598(5) 0.058(3) Uiso 1 1 d . . .
H1 H 1.2372 -0.9903 0.7893 0.086 Uiso 1 1 calc R . .
O2 O 1.120(3) -1.1946(19) 0.7712(5) 0.060(4) Uiso 1 1 d . . .
Br1 Br 1.1778(8) -1.0102(5) 0.61676(11) 0.094(11) Uani 0.43 1 d P . .
Br2 Br 1.0851(6) -0.6657(5) 0.68829(13) 0.083(11) Uani 0.57 1 d P . .
Cl1 Cl 1.1778(8) -1.0102(5) 0.61676(11) 0.094(11) Uani 0.57 1 d P . .
Cl2 Cl 1.0851(6) -0.6657(5) 0.68829(13) 0.083(11) Uani 0.43 1 d P . .
F1 F 1.053(3) -1.084(3) 0.6676(7) 0.107(6) Uiso 1 1 d . . .
C3 C 1.330(4) -1.046(3) 0.8938(8) 0.039(6) Uiso 1 1 d . . .
C4 C 1.354(4) -1.158(3) 0.9599(8) 0.08(6) Uani 1 1 d . . .
O3 O 1.398(3) -0.912(2) 0.8818(6) 0.063(4) Uiso 1 1 d . . .
H3 H 1.3908 -0.8437 0.8487 0.094 Uiso 1 1 calc R . .
O4 O 1.276(3) -1.0773(18) 0.8651(5) 0.10(4) Uani 1 1 d . . .
Br3 Br 1.4207(5) -1.3935(3) 0.94379(11) 0.074(9) Uani 0.66 1 d P . .
Br4 Br 1.3895(8) -0.9826(5) 1.02085(12) 0.068(11) Uani 0.34 1 d P . .
Cl3 Cl 1.4207(5) -1.3935(3) 0.94379(11) 0.074(9) Uani 0.34 1 d P . .
Cl4 Cl 1.3895(8) -0.9826(5) 1.02085(12) 0.068(11) Uani 0.66 1 d P . .
F2 F 1.281(3) -1.2446(19) 0.9780(4) 0.063(4) Uiso 1 1 d . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 O1 1.21(5) . ?
C1 O2 1.27(4) . ?
C1 C2 1.68(6) . ?
C2 F1 1.05(5) . ?
C2 Cl2 1.800(18) . ?
C2 Br2 1.800(18) . ?
C2 Br1 2.03(5) . ?
C2 Cl1 2.03(5) . ?
C3 O4 1.10(7) . ?
C3 O3 1.40(6) . ?
C3 C4 1.60(3) . ?
C4 F2 1.37(7) . ?
C4 Cl4 1.77(3) . ?
C4 Br4 1.77(3) . ?
C4 Br3 1.83(4) . ?
C4 Cl3 1.83(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
O1 C1 O2 130(2) . . ?
O1 C1 C2 123.2(19) . . ?
O2 C1 C2 105(4) . . ?
F1 C2 C1 116(2) . . ?
F1 C2 Cl2 132(4) . . ?
C1 C2 Cl2 107(2) . . ?
F1 C2 Br2 132(4) . . ?
C1 C2 Br2 107(2) . . ?
Cl2 C2 Br2 0.0(7) . . ?
F1 C2 Br1 94(2) . . ?
C1 C2 Br1 92(3) . . ?
Cl2 C2 Br1 102.8(19) . . ?
Br2 C2 Br1 102.8(19) . . ?
F1 C2 Cl1 94(2) . . ?
C1 C2 Cl1 92(3) . . ?
Cl2 C2 Cl1 102.8(19) . . ?
Br2 C2 Cl1 102.8(19) . . ?
Br1 C2 Cl1 0.00(19) . . ?
O4 C3 O3 130(2) . . ?
O4 C3 C4 127(5) . . ?
O3 C3 C4 102(4) . . ?
F2 C4 C3 101(5) . . ?
F2 C4 Cl4 109(2) . . ?
C3 C4 Cl4 117.4(14) . . ?
F2 C4 Br4 109(2) . . ?
C3 C4 Br4 117.4(14) . . ?
Cl4 C4 Br4 0.00(11) . . ?
F2 C4 Br3 106.2(14) . . ?
C3 C4 Br3 108(2) . . ?
Cl4 C4 Br3 114(3) . . ?
Br4 C4 Br3 114(3) . . ?
F2 C4 Cl3 106.2(14) . . ?
C3 C4 Cl3 108(2) . . ?
Cl4 C4 Cl3 114(3) . . ?
Br4 C4 Cl3 114(3) . . ?
Br3 C4 Cl3 0.00(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
O1 C1 C2 F1 167(4) . . . . ?
O2 C1 C2 F1 -28(5) . . . . ?
O1 C1 C2 Cl2 -33(5) . . . . ?
O2 C1 C2 Cl2 132(2) . . . . ?
O1 C1 C2 Br2 -33(5) . . . . ?
O2 C1 C2 Br2 132(2) . . . . ?
O1 C1 C2 Br1 71(3) . . . . ?
O2 C1 C2 Br1 -124(2) . . . . ?
O1 C1 C2 Cl1 71(3) . . . . ?
O2 C1 C2 Cl1 -124(2) . . . . ?
O4 C3 C4 F2 -17(5) . . . . ?
O3 C3 C4 F2 166(2) . . . . ?
O4 C3 C4 Cl4 -134(4) . . . . ?
O3 C3 C4 Cl4 48(5) . . . . ?
O4 C3 C4 Br4 -134(4) . . . . ?
O3 C3 C4 Br4 48(5) . . . . ?
O4 C3 C4 Br3 95(6) . . . . ?
O3 C3 C4 Br3 -83(3) . . . . ?
O4 C3 C4 Cl3 95(6) . . . . ?
O3 C3 C4 Cl3 -83(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.259
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.259
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.081


# AND

data_bromochlorofluorocarboxylic_acid_2
_database_code_depnum_ccdc_archive 'CCDC 724000'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
bromochlorofluorocarboxylic acid
;
_chemical_name_common            'bromochlorofluorocarboxylic acid'
_chemical_melting_point          ?
_chemical_formula_moiety         'C2 H Br Cl F O2'
_chemical_formula_sum            'C2 H Br Cl F O2'
_chemical_formula_weight         191.39

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P bcn'

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'

_cell_length_a                   16.169(4)
_cell_length_b                   6.0038(16)
_cell_length_c                   20.971(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2035.7(9)
_cell_formula_units_Z            16
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3964
_cell_measurement_theta_min      3.62
_cell_measurement_theta_max      24.97

_exptl_crystal_description       disc
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.470
_exptl_crystal_size_mid          0.460
_exptl_crystal_size_min          0.085
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.498
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1440
_exptl_absorpt_coefficient_mu    8.503
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.32
_exptl_absorpt_correction_T_max  0.49
_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_special_details           
;
High-pressure measurement at 0.59 GPa.
;

_diffrn_ambient_temperature      293(2)
_diffrn_ambient_pressure         590000
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Kuma KM4CCD κ geometry'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7980
_diffrn_reflns_av_R_equivalents  0.0693
_diffrn_reflns_av_sigmaI/netI    0.0299
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.62
_diffrn_reflns_theta_max         24.97
_reflns_number_total             706
_reflns_number_gt                628
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis (Oxford Diffraction, 2004)'
_computing_cell_refinement       'CrysAlis (Oxford Diffraction, 2004)'
_computing_data_reduction        'CrysAlis (Oxford Diffraction, 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'X-seed 2.0'
_computing_publication_material  'X-seed 2.0'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0789P)²+20.2760P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         706
_refine_ls_number_parameters     122
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0694
_refine_ls_R_factor_gt           0.0616
_refine_ls_wR_factor_ref         0.1530
_refine_ls_wR_factor_gt          0.1475
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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_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_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) . . . . ?

_diffrn_measured_fraction_theta_max 0.396
_diffrn_reflns_theta_full        24.97
_diffrn_measured_fraction_theta_full 0.396
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.091


# AND

data_bromochlorofluorocarboxylic_acid_3
_database_code_depnum_ccdc_archive 'CCDC 724001'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
bromochlorofluorocarboxylic acid
;
_chemical_name_common            'bromochlorofluorocarboxylic acid'
_chemical_melting_point          ?
_chemical_formula_moiety         'C2 H Br Cl F O2'
_chemical_formula_sum            'C2 H Br Cl F O2'
_chemical_formula_weight         191.39

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.898(2)
_cell_length_b                   7.840(3)
_cell_length_c                   8.043(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.553(14)
_cell_angle_gamma                90.00
_cell_volume                     495.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1261
_cell_measurement_theta_min      3.64
_cell_measurement_theta_max      25.0

_exptl_crystal_description       disc
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.470
_exptl_crystal_size_mid          0.460
_exptl_crystal_size_min          0.085
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.565
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             360
_exptl_absorpt_coefficient_mu    8.731
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.33
_exptl_absorpt_correction_T_max  0.488
_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_special_details           
;
High-pressure measurement at 0.80 GPa.
;

_diffrn_ambient_temperature      293(2)
_diffrn_ambient_pressure         800000
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Kuma KM4CCD κ geometry'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2252
_diffrn_reflns_av_R_equivalents  0.0508
_diffrn_reflns_av_sigmaI/netI    0.0220
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.64
_diffrn_reflns_theta_max         25.00
_reflns_number_total             320
_reflns_number_gt                308
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis (Oxford Diffraction, 2004)'
_computing_cell_refinement       'CrysAlis (Oxford Diffraction, 2004)'
_computing_data_reduction        'CrysAlis (Oxford Diffraction, 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'X-seed 2.0'
_computing_publication_material  'X-seed 2.0'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0959P)²+4.4939P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         320
_refine_ls_number_parameters     55
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0575
_refine_ls_wR_factor_ref         0.1751
_refine_ls_wR_factor_gt          0.1732
_refine_ls_goodness_of_fit_ref   1.203
_refine_ls_restrained_S_all      1.203
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
Br1 Br 0.4764(4) 0.1409(4) -0.1938(3) 0.0499(13) Uani 0.451(9) 1 d P . .
Br2 Br 0.2447(3) -0.0256(3) -0.4786(2) 0.0462(11) Uani 0.549(9) 1 d P . .
Cl1 Cl 0.4764(4) 0.1409(4) -0.1938(3) 0.0499(13) Uani 0.549(9) 1 d P . .
Cl2 Cl 0.2447(3) -0.0256(3) -0.4786(2) 0.0462(11) Uani 0.451(9) 1 d P . .
F1 F 0.2103(14) 0.2788(14) -0.3476(11) 0.058(3) Uani 1 1 d . . .
C1 C 0.138(2) 0.057(2) -0.1712(17) 0.031(4) Uiso 1 1 d . . .
C2 C 0.2589(19) 0.1204(18) -0.2967(15) 0.027(3) Uiso 1 1 d . . .
O1 O 0.1882(15) -0.0742(14) -0.0870(12) 0.039(3) Uani 1 1 d . . .
O2 O 0.0064(16) 0.1356(16) -0.1606(12) 0.040(3) Uani 1 1 d . . .
H1 H 0.1234 -0.0926 -0.0153 0.058 Uiso 1 1 calc R . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
Br1 C2 1.840(16) . ?
Br2 C2 1.853(13) . ?
Cl1 C2 1.840(16) . ?
Cl2 C2 1.853(13) . ?
F1 C2 1.352(17) . ?
C1 O2 1.220(18) . ?
C1 O1 1.273(17) . ?
C1 C2 1.536(19) . ?

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 126.4(12) . . ?
O2 C1 C2 118.1(13) . . ?
O1 C1 C2 115.5(12) . . ?
F1 C2 C1 108.7(10) . . ?
F1 C2 Br1 106.3(9) . . ?
C1 C2 Br1 110.2(10) . . ?
F1 C2 Cl1 106.3(9) . . ?
C1 C2 Cl1 110.2(10) . . ?
Br1 C2 Cl1 0.0(2) . . ?
F1 C2 Br2 109.5(9) . . ?
C1 C2 Br2 109.0(10) . . ?
Br1 C2 Br2 113.1(7) . . ?
Cl1 C2 Br2 113.1(7) . . ?
F1 C2 Cl2 109.5(9) . . ?
C1 C2 Cl2 109.0(10) . . ?
Br1 C2 Cl2 113.1(7) . . ?
Cl1 C2 Cl2 113.1(7) . . ?
Br2 C2 Cl2 0.00(15) . . ?

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 13(2) . . . . ?
O1 C1 C2 F1 -166.1(14) . . . . ?
O2 C1 C2 Br1 129.6(16) . . . . ?
O1 C1 C2 Br1 -50.0(17) . . . . ?
O2 C1 C2 Cl1 129.6(16) . . . . ?
O1 C1 C2 Cl1 -50.0(17) . . . . ?
O2 C1 C2 Br2 -105.8(17) . . . . ?
O1 C1 C2 Br2 74.6(16) . . . . ?
O2 C1 C2 Cl2 -105.8(17) . . . . ?
O1 C1 C2 Cl2 74.6(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.366
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.366
_refine_diff_density_max         0.564
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.125


# AND

data_bromochlorofluorocarboxylic_acid_4
_database_code_depnum_ccdc_archive 'CCDC 724002'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
bromochlorofluorocarboxylic acid
;
_chemical_name_common            'bromochlorofluorocarboxylic acid'
_chemical_melting_point          ?
_chemical_formula_moiety         'C2 H Br Cl F O2'
_chemical_formula_sum            'C2 H Br Cl F O2'
_chemical_formula_weight         191.39

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.730(3)
_cell_length_b                   7.685(3)
_cell_length_c                   7.997(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.74(2)
_cell_angle_gamma                90.00
_cell_volume                     472.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1979
_cell_measurement_theta_min      3.69
_cell_measurement_theta_max      24.98

_exptl_crystal_description       disc
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.460
_exptl_crystal_size_mid          0.450
_exptl_crystal_size_min          0.085
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.689
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             360
_exptl_absorpt_coefficient_mu    9.154
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.333
_exptl_absorpt_correction_T_max  0.486
_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_special_details           
;
High-pressure measurement at 1.37 GPa.
;

_diffrn_ambient_temperature      293(2)
_diffrn_ambient_pressure         1370000
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Kuma KM4CCD κ geometry'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            1961
_diffrn_reflns_av_R_equivalents  0.0609
_diffrn_reflns_av_sigmaI/netI    0.0253
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.69
_diffrn_reflns_theta_max         24.98
_reflns_number_total             277
_reflns_number_gt                259
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis (Oxford Diffraction, 2004)'
_computing_cell_refinement       'CrysAlis (Oxford Diffraction, 2004)'
_computing_data_reduction        'CrysAlis (Oxford Diffraction, 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'X-seed 2.0'
_computing_publication_material  'X-seed 2.0'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0616P)²+3.4947P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         277
_refine_ls_number_parameters     55
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0443
_refine_ls_wR_factor_ref         0.1201
_refine_ls_wR_factor_gt          0.1173
_refine_ls_goodness_of_fit_ref   1.173
_refine_ls_restrained_S_all      1.173
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
Br1 Br 0.4833(3) 0.1425(3) -0.1935(2) 0.0363(9) Uani 0.458(8) 1 d P . .
Br2 Br 0.2454(2) -0.0206(2) -0.4835(2) 0.0363(8) Uani 0.542(8) 1 d P . .
Cl1 Cl 0.4833(3) 0.1425(3) -0.1935(2) 0.0363(9) Uani 0.542(8) 1 d P . .
Cl2 Cl 0.2454(2) -0.0206(2) -0.4835(2) 0.0363(8) Uani 0.458(8) 1 d P . .
F1 F 0.2084(10) 0.2856(11) -0.3491(8) 0.038(2) Uani 1 1 d . . .
C1 C 0.1358(17) 0.0576(17) -0.1724(15) 0.021(3) Uiso 1 1 d . . .
C2 C 0.2597(16) 0.1220(17) -0.2957(14) 0.027(3) Uiso 1 1 d . . .
O1 O 0.1906(12) -0.0754(13) -0.0893(10) 0.034(3) Uani 1 1 d . . .
O2 O 0.0002(12) 0.1393(12) -0.1635(10) 0.034(2) Uani 1 1 d . . .
H1 H 0.1263 -0.0957 -0.0161 0.050 Uiso 1 1 calc R . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
Br1 C2 1.844(14) . ?
Br2 C2 1.854(13) . ?
Cl1 C2 1.844(14) . ?
Cl2 C2 1.854(13) . ?
F1 C2 1.374(14) . ?
C1 O2 1.230(14) . ?
C1 O1 1.269(14) . ?
C1 C2 1.524(15) . ?

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 128.5(9) . . ?
O2 C1 C2 117.8(10) . . ?
O1 C1 C2 113.7(10) . . ?
F1 C2 C1 108.5(9) . . ?
F1 C2 Br1 106.8(8) . . ?
C1 C2 Br1 111.3(9) . . ?
F1 C2 Cl1 106.8(8) . . ?
C1 C2 Cl1 111.3(9) . . ?
Br1 C2 Cl1 0.00(19) . . ?
F1 C2 Br2 107.3(8) . . ?
C1 C2 Br2 110.0(10) . . ?
Br1 C2 Br2 112.7(6) . . ?
Cl1 C2 Br2 112.7(6) . . ?
F1 C2 Cl2 107.3(8) . . ?
C1 C2 Cl2 110.0(10) . . ?
Br1 C2 Cl2 112.7(6) . . ?
Cl1 C2 Cl2 112.7(6) . . ?
Br2 C2 Cl2 0.00(11) . . ?

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 12.7(18) . . . . ?
O1 C1 C2 F1 -166.3(13) . . . . ?
O2 C1 C2 Br1 129.8(13) . . . . ?
O1 C1 C2 Br1 -49.1(17) . . . . ?
O2 C1 C2 Cl1 129.8(13) . . . . ?
O1 C1 C2 Cl1 -49.1(17) . . . . ?
O2 C1 C2 Br2 -104.5(14) . . . . ?
O1 C1 C2 Br2 76.6(15) . . . . ?
O2 C1 C2 Cl2 -104.5(14) . . . . ?
O1 C1 C2 Cl2 76.6(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.335
_diffrn_reflns_theta_full        24.98
_diffrn_measured_fraction_theta_full 0.335
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.101

# AND

data_bromochlorofluorocarboxylic_acid_5
_database_code_depnum_ccdc_archive 'CCDC 724003'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
bromochlorofluorocarboxylic acid
;
_chemical_name_common            'bromochlorofluorocarboxylic acid'
_chemical_melting_point          ?
_chemical_formula_moiety         'C2 H Br Cl F O2'
_chemical_formula_sum            'C2 H Br Cl F O2'
_chemical_formula_weight         191.39

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P bcn'

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'

_cell_length_a                   15.274(4)
_cell_length_b                   5.8537(3)
_cell_length_c                   20.7562(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1855.9(5)
_cell_formula_units_Z            16
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5354
_cell_measurement_theta_min      3.73
_cell_measurement_theta_max      24.98

_exptl_crystal_description       disc
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.430
_exptl_crystal_size_min          0.085
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.740
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1440
_exptl_absorpt_coefficient_mu    9.327
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.33
_exptl_absorpt_correction_T_max  0.486
_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_special_details           
;
High-pressure measurement at 1.93 GPa.
;

_diffrn_ambient_temperature      293(2)
_diffrn_ambient_pressure         1930000
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Kuma KM4CCD κ geometry'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7353
_diffrn_reflns_av_R_equivalents  0.1088
_diffrn_reflns_av_sigmaI/netI    0.0348
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.73
_diffrn_reflns_theta_max         24.98
_reflns_number_total             439
_reflns_number_gt                407
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis (Oxford Diffraction, 2004)'
_computing_cell_refinement       'CrysAlis (Oxford Diffraction, 2004)'
_computing_data_reduction        'CrysAlis (Oxford Diffraction, 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'X-seed 2.0'
_computing_publication_material  'X-seed 2.0'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1475P)²+59.0716P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         439
_refine_ls_number_parameters     82
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1144
_refine_ls_R_factor_gt           0.1076
_refine_ls_wR_factor_ref         0.2815
_refine_ls_wR_factor_gt          0.2752
_refine_ls_goodness_of_fit_ref   1.241
_refine_ls_restrained_S_all      1.241
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 1.161(8) -1.035(5) 0.7428(14) 0.037(8) Uiso 1 1 d . . .
C2 C 1.084(6) -0.975(4) 0.6801(11) 0.026(7) Uiso 1 1 d . . .
O1 O 1.208(5) -0.918(4) 0.7599(11) 0.057(7) Uiso 1 1 d . . .
H1 H 1.2176 -0.9426 0.7982 0.086 Uiso 1 1 calc R . .
O2 O 1.110(5) -1.203(4) 0.7692(9) 0.11(6) Uani 1 1 d . . .
Br1 Br 1.1834(13) -1.0140(9) 0.6151(2) 0.058(16) Uani 0.34 1 d P . .
Br2 Br 1.0742(12) -0.6677(9) 0.6839(2) 0.070(15) Uani 0.66 1 d P . .
Cl1 Cl 1.1834(13) -1.0140(9) 0.6151(2) 0.058(16) Uani 0.66 1 d P . .
Cl2 Cl 1.0742(12) -0.6677(9) 0.6839(2) 0.070(15) Uani 0.34 1 d P . .
F1 F 1.045(7) -1.103(6) 0.6618(15) 0.125(12) Uiso 1 1 d . . .
C3 C 1.327(7) -1.036(4) 0.8992(11) 0.022(6) Uiso 1 1 d . . .
C4 C 1.353(7) -1.149(4) 0.9633(12) 0.027(7) Uiso 1 1 d . . .
O3 O 1.405(4) -0.900(3) 0.8848(8) 0.034(5) Uiso 1 1 d . . .
H3 H 1.3968 -0.8291 0.8513 0.051 Uiso 1 1 calc R . .
O4 O 1.271(4) -1.080(3) 0.8668(8) 0.031(5) Uiso 1 1 d . . .
Br3 Br 1.4203(9) -1.4099(6) 0.94708(16) 0.0376(14) Uiso 0.68 1 d P . .
Br4 Br 1.3926(12) -0.9829(7) 1.0272(2) 0.0323(15) Uiso 0.32 1 d P . .
Cl3 Cl 1.4203(9) -1.4099(6) 0.94708(16) 0.0376(14) Uiso 0.32 1 d P . .
Cl4 Cl 1.3926(12) -0.9829(7) 1.0272(2) 0.0323(15) Uiso 0.68 1 d P . .
F2 F 1.259(5) -1.232(3) 0.9826(8) 0.048(5) Uiso 1 1 d . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 O1 1.06(10) . ?
C1 O2 1.36(8) . ?
C1 C2 1.79(11) . ?
C2 F1 1.03(8) . ?
C2 Cl2 1.81(3) . ?
C2 Br2 1.81(3) . ?
C2 Cl1 2.04(7) . ?
C2 Br1 2.04(7) . ?
C3 O4 1.11(9) . ?
C3 O3 1.46(10) . ?
C3 C4 1.54(5) . ?
C4 F2 1.56(12) . ?
C4 Cl4 1.75(4) . ?
C4 Br4 1.75(4) . ?
C4 Br3 1.87(6) . ?
C4 Cl3 1.87(6) . ?

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
O1 C1 O2 136(3) . . ?
O1 C1 C2 124(3) . . ?
O2 C1 C2 94(7) . . ?
F1 C2 Cl2 134(8) . . ?
F1 C2 Br2 134(8) . . ?
Cl2 C2 Br2 0.0(3) . . ?
F1 C2 C1 120(4) . . ?
Cl2 C2 C1 103(3) . . ?
Br2 C2 C1 103(3) . . ?
F1 C2 Cl1 96(5) . . ?
Cl2 C2 Cl1 102(3) . . ?
Br2 C2 Cl1 102(3) . . ?
C1 C2 Cl1 88(5) . . ?
F1 C2 Br1 96(5) . . ?
Cl2 C2 Br1 102(3) . . ?
Br2 C2 Br1 102(3) . . ?
C1 C2 Br1 88(5) . . ?
Cl1 C2 Br1 0.00(17) . . ?
O4 C3 O3 128(3) . . ?
O4 C3 C4 129(6) . . ?
O3 C3 C4 101(7) . . ?
F2 C4 C3 97(7) . . ?
F2 C4 Cl4 107(3) . . ?
C3 C4 Cl4 120(2) . . ?
F2 C4 Br4 107(3) . . ?
C3 C4 Br4 120(2) . . ?
Cl4 C4 Br4 0.00(18) . . ?
F2 C4 Br3 107(2) . . ?
C3 C4 Br3 110(3) . . ?
Cl4 C4 Br3 114(5) . . ?
Br4 C4 Br3 114(5) . . ?
F2 C4 Cl3 107(2) . . ?
C3 C4 Cl3 110(3) . . ?
Cl4 C4 Cl3 114(5) . . ?
Br4 C4 Cl3 114(5) . . ?
Br3 C4 Cl3 0.0(2) . . ?

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
O1 C1 C2 F1 172(10) . . . . ?
O2 C1 C2 F1 -31(9) . . . . ?
O1 C1 C2 Cl2 -26(10) . . . . ?
O2 C1 C2 Cl2 131(4) . . . . ?
O1 C1 C2 Br2 -26(10) . . . . ?
O2 C1 C2 Br2 131(4) . . . . ?
O1 C1 C2 Cl1 76(8) . . . . ?
O2 C1 C2 Cl1 -128(3) . . . . ?
O1 C1 C2 Br1 76(8) . . . . ?
O2 C1 C2 Br1 -128(3) . . . . ?
O4 C3 C4 F2 -28(7) . . . . ?
O3 C3 C4 F2 166(3) . . . . ?
O4 C3 C4 Cl4 -142(6) . . . . ?
O3 C3 C4 Cl4 51(8) . . . . ?
O4 C3 C4 Br4 -142(6) . . . . ?
O3 C3 C4 Br4 51(8) . . . . ?
O4 C3 C4 Br3 83(10) . . . . ?
O3 C3 C4 Br3 -83(4) . . . . ?
O4 C3 C4 Cl3 83(10) . . . . ?
O3 C3 C4 Cl3 -83(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.269
_diffrn_reflns_theta_full        24.98
_diffrn_measured_fraction_theta_full 0.269
_refine_diff_density_max         0.685
_refine_diff_density_min         -0.679
_refine_diff_density_rms         0.179


# END


