#------------------------------------------------------------------------------
#$Date: 2016-02-20 01:53:41 +0100 (Sat 20 de Feb de 2016) $
#$Revision: 176768 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/57/2105703.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2105703
loop_
_publ_author_name
'Day, Graeme M.'
'Cooper, Timothy G.'
'Cruz-Cabeza, Aurora J.'
'Hejczyk, Katarzyna E.'
'Ammon, Herman L.'
'Boerrigter, Stephan X. M.'
'Tan, Jeffrey S.'
'Della Valle, Raffaele G.'
'Venuti, Elisabetta'
'Jose, Jovan'
'Gadre, Shridhar R.'
'Desiraju, Gautam R.'
'Thakur, Tejender S.'
'van Eijck, Bouke P.'
'Facelli, Julio C.'
'Bazterra, Victor E.'
'Ferraro, Marta B.'
'Hofmann, Detlef W. M.'
'Neumann, Marcus A.'
'Leusen, Frank J. J.'
'Kendrick, John'
'Price, Sarah L.'
'Misquitta, Alston J.'
'Karamertzanis, Panagiotis G.'
'Welch, Gareth W. A.'
'Scheraga, Harold A.'
'Arnautova, Yelena A.'
'Schmidt, Martin U.'
'van de Streek, Jacco'
'Wolf, Alexandra K.'
'Schweizer, Bernd'
_publ_section_title
;
 Significant progress in predicting the crystal structures of small
 organic molecules -- a report on the fourth blind test
;
_journal_issue                   2
_journal_name_full
'Acta Crystallographica Section B Structural Science'
_journal_page_first              107
_journal_page_last               125
_journal_paper_doi               10.1107/S0108768109004066
_journal_volume                  65
_journal_year                    2009
_chemical_formula_sum            'C6 H2 Br2 Cl F'
_chemical_formula_weight         288.35
_chemical_name_systematic
;
2,6-dibromo-1-chloro-4-fluorobenzene
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXTL
_cell_angle_alpha                90.00
_cell_angle_beta                 93.636(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   3.8943(5)
_cell_length_b                   13.5109(17)
_cell_length_c                   14.4296(17)
_cell_measurement_reflns_used    2210
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      23.3
_cell_measurement_theta_min      2.8
_cell_volume                     757.69(16)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
;
Bruker SMART area detector diffractometer
;
_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  0.040
_diffrn_reflns_av_sigmaI/netI    0.029
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -2
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3351
_diffrn_reflns_theta_full        23.26
_diffrn_reflns_theta_max         23.26
_diffrn_reflns_theta_min         2.07
_diffrn_standards_decay_%        'less than 1'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    10.981
_exptl_absorpt_correction_T_max  0.33
_exptl_absorpt_correction_T_min  0.16
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS; Shekdrick, 1996; Blessing, 1995
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.528
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.635
_refine_diff_density_min         -1.006
_refine_diff_density_rms         0.164
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.08
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     92
_refine_ls_number_reflns         1091
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.08
_refine_ls_R_factor_all          0.039
_refine_ls_R_factor_gt           0.036
_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)+(0.062P)²+0.024P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.088
_refine_ls_wR_factor_ref         0.089
_reflns_number_gt                1011
_reflns_number_total             1091
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            bk5081sup1.cif
_cod_data_source_block           expt_XIII
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               2105703
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'
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
Br2 Br 1.01129(14) 0.14882(3) 0.90258(3) 0.0244(2) Uani 1 1 d .
Br6 Br 0.39102(13) 0.40777(4) 0.62652(3) 0.0249(2) Uani 1 1 d .
Cl1 Cl 0.6619(4) 0.35899(9) 0.83886(9) 0.0288(5) Uani 1.000(5) 1 d .
F4 F 0.7773(10) 0.0514(2) 0.5594(2) 0.0455(10) Uani 1 1 d .
C1 C 0.6950(12) 0.2676(3) 0.7563(3) 0.0189(11) Uani 1 1 d .
C2 C 0.8441(12) 0.1773(3) 0.7801(3) 0.0193(10) Uani 1 1 d .
C3 C 0.8718(13) 0.1031(3) 0.7138(4) 0.0240(12) Uani 1 1 d .
H3 H 0.9706 0.0407 0.7300 0.029 Uiso 1 1 calc R
C4 C 0.7523(15) 0.1231(4) 0.6244(3) 0.0264(12) Uani 1 1 d .
C5 C 0.6035(14) 0.2116(4) 0.5968(3) 0.0258(12) Uani 1 1 d .
H5 H 0.5198 0.2226 0.5344 0.031 Uiso 1 1 calc R
C6 C 0.5814(13) 0.2838(3) 0.6641(3) 0.0206(11) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br2 0.0240(4) 0.0266(4) 0.0223(4) 0.00311(19) -0.0006(2) -0.0001(2)
Br6 0.0253(4) 0.0228(4) 0.0265(4) 0.0032(2) 0.0022(2) 0.0040(2)
Cl1 0.0403(9) 0.0230(8) 0.0232(8) -0.0046(5) 0.0036(6) 0.0015(5)
F4 0.080(3) 0.0305(18) 0.0273(18) -0.0075(14) 0.0117(17) 0.0153(18)
C1 0.020(3) 0.019(2) 0.018(3) 0.001(2) 0.009(2) -0.001(2)
C2 0.011(2) 0.027(3) 0.020(3) 0.004(2) 0.003(2) -0.002(2)
C3 0.026(3) 0.019(3) 0.028(3) -0.001(2) 0.014(2) 0.006(2)
C4 0.037(3) 0.020(3) 0.024(3) -0.006(2) 0.008(2) 0.001(2)
C5 0.029(3) 0.031(3) 0.017(3) -0.001(2) 0.003(2) 0.000(2)
C6 0.016(3) 0.022(3) 0.025(3) 0.005(2) 0.006(2) -0.002(2)
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'
F F 0.0171 0.0103 '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'
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
C2 C1 C6 118.6(4)
C2 C1 Cl1 120.5(4)
C6 C1 Cl1 120.9(4)
C1 C2 C3 120.8(5)
C1 C2 Br2 121.8(4)
C3 C2 Br2 117.4(4)
C4 C3 C2 117.9(5)
C4 C3 H3 121.1
C2 C3 H3 121.1
F4 C4 C3 118.4(5)
F4 C4 C5 117.9(5)
C3 C4 C5 123.7(5)
C4 C5 C6 117.0(5)
C4 C5 H5 121.5
C6 C5 H5 121.5
C5 C6 C1 122.0(5)
C5 C6 Br6 117.6(4)
C1 C6 Br6 120.4(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br2 C2 1.884(5)
Br6 C6 1.897(5)
Cl1 C1 1.727(5)
F4 C4 1.355(6)
C1 C2 1.385(6)
C1 C6 1.393(7)
C2 C3 1.395(7)
C3 C4 1.370(8)
C3 H3 0.9500
C4 C5 1.377(7)
C5 C6 1.382(7)
C5 H5 0.9500
