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#$Date: 2016-03-26 14:27:39 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180263 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/49/7114977.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_7114977
loop_
_publ_author_name
'Bond, Andrew D.'
'Griffiths, Joanna'
'Rawson, Jeremy M.'
'Hulliger, Jürg'
_publ_section_title
;
 Inducing structural polarity using fluorinated organics: X-ray crystal
 structures of p-XC6F4CN (X = Cl, Br, I)Electronic supplementary data
 (ESI) available: the crystal structure of p-BrC6F4CN in .pdb format. See
 http://www.rsc.org/suppdata/cc/b1/b107665p/
;
_journal_issue                   23
_journal_name_full               'Chemical Communications'
_journal_page_first              2488
_journal_paper_doi               10.1039/b107665p
_journal_year                    2001
_chemical_formula_moiety         'C7 Br F4 N'
_chemical_formula_sum            'C7 Br F4 N'
_chemical_formula_weight         253.99
_chemical_name_systematic
; 
4-bromo-2,3,5,6-fluorobenzonitrile 
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_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            4
_cell_length_a                   14.6736(12)
_cell_length_b                   8.2804(5)
_cell_length_c                   6.1368(5)
_cell_measurement_reflns_used    3220
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     745.64(10)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_data_reduction
;
HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_publication_material  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_solution    'SIR-92 (Altomare et al. 1994)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice ω and φ 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  0.0679
_diffrn_reflns_av_sigmaI/netI    0.0743
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            4047
_diffrn_reflns_theta_full        27.45
_diffrn_reflns_theta_max         27.45
_diffrn_reflns_theta_min         3.71
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.529
_exptl_absorpt_correction_T_max  0.924
_exptl_absorpt_correction_T_min  0.505
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sortav Blessing (1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.263
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.695
_refine_diff_density_min         -0.705
_refine_diff_density_rms         0.121
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1647
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0673
_refine_ls_R_factor_gt           0.0447
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0420P)²+0.0744P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0908
_refine_ls_wR_factor_ref         0.1002
_reflns_number_gt                1267
_reflns_number_total             1647
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b107665p.txt
_cod_data_source_block           jr0041a
_cod_original_sg_symbol_H-M      Pna2(1)
_cod_database_code               7114977
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, 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
Br1 Br 0.10505(3) 0.60254(6) 1.16783(17) 0.03311(19) Uani 1 1 d
F3 F 0.0608(2) -0.0055(4) 1.0020(6) 0.0378(9) Uani 1 1 d
F4 F 0.0383(2) 0.2583(4) 1.2505(5) 0.0365(9) Uani 1 1 d
F6 F 0.1884(2) 0.5711(3) 0.7166(5) 0.0351(10) Uani 1 1 d
F7 F 0.2082(2) 0.3088(4) 0.4671(5) 0.0334(8) Uani 1 1 d
N1 N 0.1477(4) -0.1043(5) 0.4800(10) 0.0396(13) Uani 1 1 d
C1 C 0.1422(4) 0.0056(7) 0.5911(10) 0.0294(14) Uani 1 1 d
C2 C 0.1334(4) 0.1452(7) 0.7275(10) 0.0270(14) Uani 1 1 d
C3 C 0.0912(4) 0.1378(7) 0.9313(10) 0.0274(14) Uani 1 1 d
C4 C 0.0790(4) 0.2720(8) 1.0563(10) 0.0276(14) Uani 1 1 d
C5 C 0.1136(3) 0.4206(7) 0.9867(11) 0.0274(13) Uani 1 1 d
C6 C 0.1548(4) 0.4306(6) 0.7867(10) 0.0267(14) Uani 1 1 d
C7 C 0.1652(3) 0.2962(6) 0.6576(15) 0.0274(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
Br1 0.0416(3) 0.0266(3) 0.0312(3) -0.0087(3) 0.0007(4) 0.0018(2)
F3 0.049(2) 0.0239(17) 0.041(2) 0.0030(17) 0.0011(17) -0.0113(16)
F4 0.049(2) 0.0345(18) 0.026(2) -0.0040(15) 0.0098(16) -0.0094(17)
F6 0.055(2) 0.0224(14) 0.028(3) -0.0019(13) 0.0036(16) -0.0075(15)
F7 0.043(2) 0.0345(17) 0.023(2) -0.0036(14) 0.0071(15) -0.0017(17)
N1 0.050(3) 0.028(3) 0.040(4) -0.007(2) 0.002(3) 0.003(2)
C1 0.033(3) 0.023(3) 0.032(4) 0.001(2) 0.002(3) 0.001(3)
C2 0.024(3) 0.023(2) 0.034(4) -0.004(2) -0.003(2) 0.002(2)
C3 0.030(3) 0.022(3) 0.031(4) 0.001(2) -0.003(3) -0.005(2)
C4 0.028(3) 0.035(3) 0.020(3) 0.003(3) -0.001(3) -0.007(3)
C5 0.026(3) 0.024(3) 0.032(4) -0.007(2) -0.007(2) 0.002(3)
C6 0.032(3) 0.020(3) 0.028(3) 0.004(2) -0.001(3) -0.007(3)
C7 0.026(3) 0.032(2) 0.023(3) -0.003(3) -0.006(4) 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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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
N1 C1 C2 178.6(7)
C3 C2 C7 117.4(5)
C3 C2 C1 121.8(5)
C7 C2 C1 120.7(6)
F3 C3 C4 119.8(6)
F3 C3 C2 118.5(5)
C4 C3 C2 121.8(6)
F4 C4 C3 119.4(6)
F4 C4 C5 120.6(6)
C3 C4 C5 119.9(6)
C6 C5 C4 119.2(5)
C6 C5 Br1 120.7(4)
C4 C5 Br1 120.1(5)
F6 C6 C5 120.3(5)
F6 C6 C7 118.6(5)
C5 C6 C7 121.1(6)
F7 C7 C6 119.7(5)
F7 C7 C2 119.8(5)
C6 C7 C2 120.6(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C5 1.877(6)
F3 C3 1.340(6)
F4 C4 1.338(6)
F6 C6 1.335(6)
F7 C7 1.332(9)
N1 C1 1.140(7)
C1 C2 1.433(8)
C2 C3 1.397(9)
C2 C7 1.401(8)
C3 C4 1.362(9)
C4 C5 1.397(8)
C5 C6 1.371(9)
C6 C7 1.375(8)
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
N1 C1 C2 C3 102(28)
N1 C1 C2 C7 -77(28)
C7 C2 C3 F3 -179.6(5)
C1 C2 C3 F3 2.0(8)
C7 C2 C3 C4 1.6(8)
C1 C2 C3 C4 -176.8(5)
F3 C3 C4 F4 1.3(8)
C2 C3 C4 F4 -179.9(5)
F3 C3 C4 C5 177.6(5)
C2 C3 C4 C5 -3.6(9)
F4 C4 C5 C6 -179.9(5)
C3 C4 C5 C6 3.8(9)
F4 C4 C5 Br1 1.0(8)
C3 C4 C5 Br1 -175.3(4)
C4 C5 C6 F6 -180.0(5)
Br1 C5 C6 F6 -0.9(8)
C4 C5 C6 C7 -2.2(9)
Br1 C5 C6 C7 176.9(5)
F6 C6 C7 F7 0.0(9)
C5 C6 C7 F7 -177.8(5)
F6 C6 C7 C2 178.1(5)
C5 C6 C7 C2 0.3(9)
C3 C2 C7 F7 178.2(5)
C1 C2 C7 F7 -3.4(8)
C3 C2 C7 C6 0.1(8)
C1 C2 C7 C6 178.5(6)
