#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/16/7111665.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_7111665
loop_
_publ_author_name
'Mansell, Stephen M.'
'Adams, Christopher J.'
'Bramham, George'
'Haddow, Mairi F.'
'Kaim, Wolfgang'
'Norman, Nicholas C.'
'McGrady, John E.'
'Russell, Christopher A.'
'Udeen, Sally J.'
_publ_section_title
;
 Synthesis and characterisation of the persistent radical
 [BCl2(bipy)]˙
;
_journal_issue                   28
_journal_name_full               'Chemical Communications'
_journal_page_first              5070
_journal_page_last               5072
_journal_paper_doi               10.1039/c0cc00187b
_journal_volume                  46
_journal_year                    2010
_chemical_formula_moiety         'C10 H8 B Cl2 N2'
_chemical_formula_sum            'C10 H8 B Cl2 N2'
_chemical_formula_weight         237.89
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                68.821(4)
_cell_angle_beta                 80.171(4)
_cell_angle_gamma                88.519(4)
_cell_formula_units_Z            2
_cell_length_a                   6.8993(5)
_cell_length_b                   8.7488(6)
_cell_length_c                   9.2777(7)
_cell_measurement_reflns_used    1777
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      3.50
_cell_volume                     514.13(7)
_computing_cell_refinement       'Bruker Apex II'
_computing_data_collection       'Bruker Apex II'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker ShelXTL'
_computing_publication_material  'Bruker ShelXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0224
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2347
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         2.76
_exptl_absorpt_coefficient_mu    0.592
_exptl_absorpt_correction_T_max  0.965
_exptl_absorpt_correction_T_min  0.858
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'TWINABS V2008/1'
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.537
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             242
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2347
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.142
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0303
_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)+(0.0427P)²+0.3221P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0750
_refine_ls_wR_factor_ref         0.0895
_reflns_number_gt                2099
_reflns_number_total             2347
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            C0CC00187Bsup1.cif
_cod_data_source_block           3
_cod_original_sg_symbol_Hall     -P1
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7111665
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
Cl1 Cl 0.08403(8) 0.26014(7) 0.24910(7) 0.01804(15) Uani 1 1 d .
Cl2 Cl 0.51468(8) 0.23490(7) 0.27498(7) 0.01700(14) Uani 1 1 d .
N1 N 0.2280(3) 0.2787(2) 0.5110(2) 0.0141(4) Uani 1 1 d .
N2 N 0.2982(3) 0.5110(2) 0.2860(2) 0.0133(4) Uani 1 1 d .
B1 B 0.2783(4) 0.3252(3) 0.3339(3) 0.0138(5) Uani 1 1 d .
C1 C 0.1863(4) 0.1272(3) 0.6224(3) 0.0165(5) Uani 1 1 d .
H1 H 0.1819 0.0370 0.5923 0.020 Uiso 1 1 calc R
C2 C 0.1507(4) 0.1051(3) 0.7776(3) 0.0181(5) Uani 1 1 d .
H2 H 0.1211 0.0007 0.8529 0.022 Uiso 1 1 calc R
C3 C 0.1592(4) 0.2424(3) 0.8239(3) 0.0181(5) Uani 1 1 d .
H3 H 0.1365 0.2278 0.9298 0.022 Uiso 1 1 calc R
C4 C 0.2006(4) 0.3963(3) 0.7124(3) 0.0159(5) Uani 1 1 d .
H4 H 0.2061 0.4869 0.7418 0.019 Uiso 1 1 calc R
C5 C 0.2346(4) 0.4154(3) 0.5537(3) 0.0135(5) Uani 1 1 d .
C6 C 0.2760(3) 0.5570(3) 0.4161(3) 0.0130(5) Uani 1 1 d .
C7 C 0.2916(4) 0.7233(3) 0.3956(3) 0.0153(5) Uani 1 1 d .
H7 H 0.2761 0.7550 0.4823 0.018 Uiso 1 1 calc R
C8 C 0.3301(3) 0.8387(3) 0.2466(3) 0.0167(5) Uani 1 1 d .
H8 H 0.3403 0.9494 0.2314 0.020 Uiso 1 1 calc R
C9 C 0.3541(4) 0.7880(3) 0.1157(3) 0.0172(5) Uani 1 1 d .
H9 H 0.3817 0.8656 0.0144 0.021 Uiso 1 1 calc R
C10 C 0.3369(4) 0.6257(3) 0.1386(3) 0.0158(5) Uani 1 1 d .
H10 H 0.3517 0.5932 0.0525 0.019 Uiso 1 1 calc R
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
Cl1 0.0191(3) 0.0183(3) 0.0203(3) -0.0102(2) -0.0055(2) -0.0009(2)
Cl2 0.0174(3) 0.0166(3) 0.0185(3) -0.0089(2) -0.0020(2) 0.0033(2)
N1 0.0144(10) 0.0128(9) 0.0162(10) -0.0064(8) -0.0026(8) 0.0013(8)
N2 0.0142(10) 0.0123(9) 0.0149(10) -0.0065(8) -0.0028(8) 0.0002(8)
B1 0.0164(12) 0.0115(12) 0.0152(13) -0.0068(9) -0.0033(10) 0.0003(9)
C1 0.0173(11) 0.0117(10) 0.0194(12) -0.0040(9) -0.0036(9) 0.0001(9)
C2 0.0181(12) 0.0147(11) 0.0184(12) -0.0020(10) -0.0036(10) -0.0005(9)
C3 0.0144(12) 0.0250(13) 0.0139(11) -0.0066(10) -0.0006(9) 0.0014(9)
C4 0.0148(11) 0.0176(12) 0.0183(12) -0.0100(10) -0.0036(9) 0.0013(9)
C5 0.0113(11) 0.0132(11) 0.0177(12) -0.0073(9) -0.0035(9) 0.0022(8)
C6 0.0101(10) 0.0151(11) 0.0150(11) -0.0072(9) -0.0013(8) 0.0015(8)
C7 0.0134(11) 0.0153(11) 0.0204(13) -0.0095(10) -0.0046(10) 0.0008(9)
C8 0.0144(12) 0.0136(11) 0.0236(13) -0.0081(10) -0.0040(10) 0.0004(9)
C9 0.0172(12) 0.0134(11) 0.0180(12) -0.0020(9) -0.0029(9) -0.0003(9)
C10 0.0170(12) 0.0158(11) 0.0150(11) -0.0059(9) -0.0034(9) 0.0007(9)
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'
B B 0.0013 0.0007 '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'
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
C1 N1 C5 120.4(2)
C1 N1 B1 128.1(2)
C5 N1 B1 111.52(19)
C10 N2 C6 120.6(2)
C10 N2 B1 127.9(2)
C6 N2 B1 111.50(19)
N2 B1 N1 98.92(16)
N2 B1 Cl1 112.94(18)
N1 B1 Cl1 113.49(18)
N2 B1 Cl2 112.21(18)
N1 B1 Cl2 111.58(18)
Cl1 B1 Cl2 107.65(11)
N1 C1 C2 121.0(2)
N1 C1 H1 119.5
C2 C1 H1 119.5
C1 C2 C3 119.6(2)
C1 C2 H2 120.2
C3 C2 H2 120.2
C4 C3 C2 120.0(2)
C4 C3 H3 120.0
C2 C3 H3 120.0
C3 C4 C5 119.1(2)
C3 C4 H4 120.5
C5 C4 H4 120.5
N1 C5 C4 119.9(2)
N1 C5 C6 108.8(2)
C4 C5 C6 131.3(2)
N2 C6 C7 119.9(2)
N2 C6 C5 109.1(2)
C7 C6 C5 131.0(2)
C8 C7 C6 119.4(2)
C8 C7 H7 120.3
C6 C7 H7 120.3
C7 C8 C9 119.6(2)
C7 C8 H8 120.2
C9 C8 H8 120.2
C10 C9 C8 120.0(2)
C10 C9 H9 120.0
C8 C9 H9 120.0
N2 C10 C9 120.7(2)
N2 C10 H10 119.7
C9 C10 H10 119.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 B1 1.861(3)
Cl2 B1 1.878(3)
N1 C1 1.355(3)
N1 C5 1.393(3)
N1 B1 1.522(3)
N2 C10 1.359(3)
N2 C6 1.388(3)
N2 B1 1.525(3)
C1 C2 1.361(4)
C1 H1 0.9300
C2 C3 1.419(4)
C2 H2 0.9300
C3 C4 1.371(3)
C3 H3 0.9300
C4 C5 1.399(3)
C4 H4 0.9300
C5 C6 1.413(3)
C6 C7 1.402(3)
C7 C8 1.372(3)
C7 H7 0.9300
C8 C9 1.419(4)
C8 H8 0.9300
C9 C10 1.363(3)
C9 H9 0.9300
C10 H10 0.9300
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
C10 N2 B1 N1 -177.8(2)
C6 N2 B1 N1 3.6(3)
C10 N2 B1 Cl1 -57.5(3)
C6 N2 B1 Cl1 123.90(19)
C10 N2 B1 Cl2 64.4(3)
C6 N2 B1 Cl2 -114.20(19)
C1 N1 B1 N2 177.9(2)
C5 N1 B1 N2 -4.0(3)
C1 N1 B1 Cl1 58.0(3)
C5 N1 B1 Cl1 -123.94(18)
C1 N1 B1 Cl2 -63.8(3)
C5 N1 B1 Cl2 114.22(19)
C5 N1 C1 C2 -0.2(4)
B1 N1 C1 C2 177.7(2)
N1 C1 C2 C3 -0.6(4)
C1 C2 C3 C4 0.8(4)
C2 C3 C4 C5 -0.1(4)
C1 N1 C5 C4 0.9(3)
B1 N1 C5 C4 -177.3(2)
C1 N1 C5 C6 -178.6(2)
B1 N1 C5 C6 3.2(3)
C3 C4 C5 N1 -0.7(4)
C3 C4 C5 C6 178.6(2)
C10 N2 C6 C7 0.6(3)
B1 N2 C6 C7 179.3(2)
C10 N2 C6 C5 179.3(2)
B1 N2 C6 C5 -2.0(3)
N1 C5 C6 N2 -0.7(2)
C4 C5 C6 N2 179.9(3)
N1 C5 C6 C7 177.7(3)
C4 C5 C6 C7 -1.6(4)
N2 C6 C7 C8 -0.4(3)
C5 C6 C7 C8 -178.7(2)
C6 C7 C8 C9 -0.3(3)
C7 C8 C9 C10 0.7(4)
C6 N2 C10 C9 -0.2(4)
B1 N2 C10 C9 -178.6(2)
C8 C9 C10 N2 -0.5(4)
