#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:04:12 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179650 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/03/4510399.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_4510399
loop_
_publ_author_name
'Morse, Graham E.'
'Gong, Ivan'
'Kawar, Yazan'
'Lough, Alan J.'
'Bender, Timothy P.'
_publ_section_title
;
 Crystal and Solid-State Arrangement Trends of Halogenated Boron
 Subphthalocyanines
;
_journal_issue                   5
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2138
_journal_paper_doi               10.1021/cg401475b
_journal_volume                  14
_journal_year                    2014
_chemical_formula_moiety         'C24 B Br Cl12 N6, C6 H6'
_chemical_formula_sum            'C30 H6 B Br Cl12 N6'
_chemical_formula_weight         966.53
_chemical_name_common            'Br-Cl12BsubPc benzene solvate'
_chemical_name_systematic
Bromido(dodecachlorosubphthalocyaninato)boron(III)(benzene)
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 1'
_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                 107.670(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.6087(6)
_cell_length_b                   17.1155(17)
_cell_length_c                   12.3063(12)
_cell_measurement_reflns_used    9690
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.6
_cell_volume                     1727.7(3)
_computing_cell_refinement       'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius B.V., 1997-2002)'
_computing_data_reduction        Denzo-SMN
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL V6.1'
_computing_structure_refinement  'SHELXTL V6.1 (Sheldrick, 2008)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150(1)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ scans and ω scans with κ offsets'
_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  0.0641
_diffrn_reflns_av_sigmaI/netI    0.0897
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9690
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         2.56
_exptl_absorpt_coefficient_mu    2.154
_exptl_absorpt_correction_T_max  0.962
_exptl_absorpt_correction_T_min  0.838
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.858
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.487
_refine_diff_density_min         -0.717
_refine_diff_density_rms         0.097
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3849
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.1152
_refine_ls_R_factor_gt           0.0520
_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^)+(0.0518P)2^] where P=(Fo2+2Fc2)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1017
_refine_ls_wR_factor_ref         0.1234
_reflns_number_gt                2249
_reflns_number_total             3849
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cg401475b_si_007.cif
_cod_data_source_block           Br-Cl12BsubPc[benzene][k09259]
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 4510399--4510406.cif.
;
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               4510399
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -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
Br1 Br 0.50547(7) 0.2500 0.42157(6) 0.0370(2) Uani 1 2 d S
Cl1 Cl 0.82884(14) -0.05745(7) 0.76586(11) 0.0471(3) Uani 1 1 d .
Cl2 Cl 1.14283(15) -0.13602(7) 0.73705(12) 0.0532(4) Uani 1 1 d .
Cl3 Cl 1.36810(13) -0.04422(7) 0.62711(11) 0.0434(3) Uani 1 1 d .
Cl4 Cl 1.27021(12) 0.12435(6) 0.52866(10) 0.0390(3) Uani 1 1 d .
Cl5 Cl 0.42737(15) 0.15946(9) 1.10824(11) 0.0567(4) Uani 1 1 d .
Cl6 Cl 0.50381(16) 0.06738(7) 0.90965(11) 0.0544(4) Uani 1 1 d .
N1 N 0.6702(4) 0.1154(2) 0.7180(3) 0.0321(8) Uani 1 1 d .
N2 N 0.7886(4) 0.18119(19) 0.5927(3) 0.0300(8) Uani 1 1 d .
N3 N 0.6170(5) 0.2500 0.6752(4) 0.0274(11) Uani 1 2 d S
N4 N 1.0043(6) 0.2500 0.5505(4) 0.0312(12) Uani 1 2 d S
C1 C 0.7704(5) 0.1169(2) 0.6528(4) 0.0307(10) Uani 1 1 d .
C2 C 0.9038(5) 0.0646(2) 0.6523(4) 0.0322(10) Uani 1 1 d .
C3 C 0.9489(5) -0.0086(3) 0.6986(4) 0.0362(11) Uani 1 1 d .
C4 C 1.0910(5) -0.0428(2) 0.6885(4) 0.0379(11) Uani 1 1 d .
C5 C 1.1921(5) -0.0014(3) 0.6372(4) 0.0339(11) Uani 1 1 d .
C6 C 1.1509(5) 0.0727(2) 0.5942(4) 0.0330(10) Uani 1 1 d .
C7 C 1.0056(5) 0.1066(2) 0.5996(4) 0.0320(10) Uani 1 1 d .
C8 C 0.9358(5) 0.1833(3) 0.5701(3) 0.0307(10) Uani 1 1 d .
C9 C 0.6020(5) 0.1832(3) 0.7319(4) 0.0309(10) Uani 1 1 d .
C10 C 0.5426(5) 0.2089(2) 0.8262(4) 0.0340(11) Uani 1 1 d .
C11 C 0.5065(5) 0.1674(3) 0.9134(4) 0.0392(11) Uani 1 1 d .
C12 C 0.4722(5) 0.2095(3) 1.0001(4) 0.0422(12) Uani 1 1 d .
B1 B 0.6787(8) 0.2500 0.5752(6) 0.0316(17) Uani 1 2 d S
C1S C -0.0738(11) 0.2500 1.0059(9) 0.087(3) Uani 1 2 d S
H1S H -0.1291 0.2500 1.0620 0.104 Uiso 1 2 calc SR
C2S C -0.0353(8) 0.1810(5) 0.9668(7) 0.104(3) Uani 1 1 d .
H2S H -0.0674 0.1331 0.9926 0.124 Uiso 1 1 calc R
C3S C 0.0510(9) 0.1810(6) 0.8891(7) 0.111(3) Uani 1 1 d .
H3S H 0.0828 0.1330 0.8635 0.134 Uiso 1 1 calc R
C4S C 0.0907(13) 0.2500 0.8490(9) 0.107(5) Uani 1 2 d S
H4S H 0.1462 0.2500 0.7930 0.128 Uiso 1 2 calc SR
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'
N N 0.0061 0.0033 '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'
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
C9 N1 C1 116.5(3) . .
C1 N2 C8 113.3(3) . .
C1 N2 B1 123.1(4) . .
C8 N2 B1 122.3(4) . .
C9 N3 C9 113.7(5) 4_565 .
C9 N3 B1 122.5(2) 4_565 .
C9 N3 B1 122.5(2) . .
C8 N4 C8 116.9(5) . 4_565
N1 C1 N2 122.7(4) . .
N1 C1 C2 129.8(4) . .
N2 C1 C2 105.8(3) . .
C3 C2 C7 120.5(4) . .
C3 C2 C1 132.6(4) . .
C7 C2 C1 106.6(4) . .
C2 C3 C4 119.2(4) . .
C2 C3 Cl1 120.2(3) . .
C4 C3 Cl1 120.6(3) . .
C3 C4 C5 120.4(4) . .
C3 C4 Cl2 120.1(3) . .
C5 C4 Cl2 119.5(3) . .
C6 C5 C4 120.8(4) . .
C6 C5 Cl3 119.6(3) . .
C4 C5 Cl3 119.6(3) . .
C5 C6 C7 119.5(4) . .
C5 C6 Cl4 122.0(3) . .
C7 C6 Cl4 118.5(3) . .
C6 C7 C2 119.6(4) . .
C6 C7 C8 132.4(4) . .
C2 C7 C8 107.7(3) . .
N4 C8 N2 122.7(4) . .
N4 C8 C7 130.4(4) . .
N2 C8 C7 105.3(3) . .
N1 C9 N3 123.2(4) . .
N1 C9 C10 129.3(4) . .
N3 C9 C10 105.2(4) . .
C11 C10 C10 120.5(3) . 4_565
C11 C10 C9 131.7(4) . .
C10 C10 C9 107.4(2) 4_565 .
C12 C11 C10 118.3(4) . .
C12 C11 Cl6 122.3(3) . .
C10 C11 Cl6 119.4(3) . .
C12 C12 C11 121.2(3) 4_565 .
C12 C12 Cl5 119.82(16) 4_565 .
C11 C12 Cl5 119.0(4) . .
N3 B1 N2 104.7(4) . 4_565
N3 B1 N2 104.7(4) . .
N2 B1 N2 104.9(5) 4_565 .
N3 B1 Br1 115.4(4) . .
N2 B1 Br1 113.1(3) 4_565 .
N2 B1 Br1 113.1(3) . .
C2S C1S C2S 121.4(11) . 4_565
C1S C2S C3S 119.2(9) . .
C4S C3S C2S 119.9(10) . .
C3S C4S C3S 120.1(12) 4_565 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 B1 2.022(7) .
Cl1 C3 1.724(4) .
Cl2 C4 1.715(4) .
Cl3 C5 1.721(4) .
Cl4 C6 1.729(4) .
Cl5 C12 1.721(4) .
Cl6 C11 1.713(5) .
N1 C9 1.335(5) .
N1 C1 1.344(5) .
N2 C1 1.362(5) .
N2 C8 1.378(5) .
N2 B1 1.485(5) .
N3 C9 1.367(5) 4_565
N3 C9 1.367(5) .
N3 B1 1.480(8) .
N4 C8 1.340(5) .
N4 C8 1.340(5) 4_565
C1 C2 1.457(6) .
C2 C3 1.382(6) .
C2 C7 1.432(6) .
C3 C4 1.396(6) .
C4 C5 1.411(6) .
C5 C6 1.379(6) .
C6 C7 1.399(5) .
C7 C8 1.444(6) .
C9 C10 1.470(6) .
C10 C11 1.398(6) .
C10 C10 1.407(8) 4_565
C11 C12 1.391(6) .
C12 C12 1.387(9) 4_565
B1 N2 1.485(5) 4_565
C1S C2S 1.354(10) .
C1S C2S 1.354(10) 4_565
C2S C3S 1.378(11) .
C3S C4S 1.362(10) .
C4S C3S 1.362(10) 4_565
