#------------------------------------------------------------------------------
#$Date: 2016-03-26 18:23:59 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180427 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/96/7209616.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_7209616
loop_
_publ_author_name
'Virdo, Jessica D.'
'Kawar, Yazan H.'
'Lough, Alan J.'
'Bender, Timothy P.'
_publ_section_title
;
 Halogen bonds can direct the solid state arrangement of phenoxy--boron
 subphthalocyanines
;
_journal_issue                   16
_journal_name_full               CrystEngComm
_journal_page_first              3187
_journal_paper_doi               10.1039/c3ce26711c
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C30 H12 B Br5 N6 O, 0.5(C6 H6)'
_chemical_formula_sum            'C33 H15 B Br5 N6 O'
_chemical_formula_weight         921.87
_chemical_name_common            (Pentabromophenolato)(subphthalocyaninato)boron
_chemical_name_systematic
;
(Pentabromophenolato)(subphthalocyaninato)boron
;
_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                115.1770(18)
_cell_angle_beta                 94.9400(19)
_cell_angle_gamma                93.6730(17)
_cell_formula_units_Z            2
_cell_length_a                   11.0395(3)
_cell_length_b                   11.7114(4)
_cell_length_c                   13.1600(4)
_cell_measurement_reflns_used    15993
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.7
_cell_volume                     1524.47(8)
_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 0.980
_diffrn_measured_fraction_theta_max 0.980
_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  0.0551
_diffrn_reflns_av_sigmaI/netI    0.0602
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15993
_diffrn_reflns_theta_full        27.58
_diffrn_reflns_theta_max         27.58
_diffrn_reflns_theta_min         2.69
_exptl_absorpt_coefficient_mu    6.631
_exptl_absorpt_correction_T_max  0.603
_exptl_absorpt_correction_T_min  0.439
_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    2.008
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             886
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.956
_refine_diff_density_min         -1.067
_refine_diff_density_rms         0.149
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     415
_refine_ls_number_reflns         6925
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0439
_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)+(0.0652P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1036
_refine_ls_wR_factor_ref         0.1132
_reflns_number_gt                5374
_reflns_number_total             6925
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c3ce26711c.txt
_cod_data_source_block           k1186
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_database_code               7209616
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
Br1 Br 1.04095(4) 0.33327(4) 0.43589(4) 0.02771(12) Uani 1 1 d .
Br2 Br 1.22751(3) 0.11126(4) 0.33914(4) 0.02868(12) Uani 1 1 d .
Br3 Br 1.13517(4) -0.18184(4) 0.29638(4) 0.03326(13) Uani 1 1 d .
Br4 Br 0.85031(4) -0.25323(4) 0.32678(3) 0.02562(12) Uani 1 1 d .
Br5 Br 0.66056(4) -0.03130(4) 0.39513(4) 0.02839(12) Uani 1 1 d .
O1 O 0.7812(2) 0.2162(2) 0.4085(2) 0.0216(6) Uani 1 1 d .
N1 N 0.6415(3) 0.3247(3) 0.3343(3) 0.0195(7) Uani 1 1 d .
N2 N 0.7773(3) 0.4726(3) 0.3077(3) 0.0213(7) Uani 1 1 d .
N3 N 0.8126(3) 0.2559(3) 0.2389(3) 0.0204(7) Uani 1 1 d .
N4 N 0.8028(3) 0.0439(3) 0.0953(3) 0.0239(8) Uani 1 1 d .
N5 N 0.6517(3) 0.1060(3) 0.2206(3) 0.0198(7) Uani 1 1 d .
N6 N 0.4614(3) 0.1769(3) 0.2760(3) 0.0230(7) Uani 1 1 d .
C1 C 0.5176(3) 0.2964(4) 0.3256(3) 0.0221(9) Uani 1 1 d .
C2 C 0.4664(3) 0.4158(4) 0.3520(3) 0.0211(8) Uani 1 1 d .
C3 C 0.3463(4) 0.4458(4) 0.3582(3) 0.0254(9) Uani 1 1 d .
H3A H 0.2804 0.3836 0.3469 0.030 Uiso 1 1 calc R
C4 C 0.3263(4) 0.5702(4) 0.3816(4) 0.0298(10) Uani 1 1 d .
H4A H 0.2452 0.5930 0.3853 0.036 Uiso 1 1 calc R
C5 C 0.4228(4) 0.6619(4) 0.3996(4) 0.0285(10) Uani 1 1 d .
H5A H 0.4062 0.7469 0.4192 0.034 Uiso 1 1 calc R
C6 C 0.5421(4) 0.6333(4) 0.3900(3) 0.0252(9) Uani 1 1 d .
H6A H 0.6067 0.6958 0.3991 0.030 Uiso 1 1 calc R
C7 C 0.5644(4) 0.5082(4) 0.3662(3) 0.0219(8) Uani 1 1 d .
C8 C 0.6745(3) 0.4434(3) 0.3436(3) 0.0197(8) Uani 1 1 d .
C9 C 0.8430(3) 0.3775(4) 0.2510(3) 0.0213(8) Uani 1 1 d .
C10 C 0.9322(3) 0.3680(4) 0.1743(3) 0.0232(9) Uani 1 1 d .
C11 C 0.9988(4) 0.4552(4) 0.1511(4) 0.0295(10) Uani 1 1 d .
H11A H 0.9946 0.5436 0.1934 0.035 Uiso 1 1 calc R
C12 C 1.0718(4) 0.4126(4) 0.0653(4) 0.0347(11) Uani 1 1 d .
H12A H 1.1183 0.4728 0.0493 0.042 Uiso 1 1 calc R
C13 C 1.0791(4) 0.2833(4) 0.0012(4) 0.0344(11) Uani 1 1 d .
H13A H 1.1301 0.2571 -0.0575 0.041 Uiso 1 1 calc R
C14 C 1.0134(4) 0.1940(4) 0.0221(4) 0.0302(10) Uani 1 1 d .
H14A H 1.0182 0.1061 -0.0217 0.036 Uiso 1 1 calc R
C15 C 0.9394(3) 0.2347(4) 0.1091(3) 0.0233(9) Uani 1 1 d .
C16 C 0.8558(3) 0.1656(4) 0.1471(3) 0.0216(8) Uani 1 1 d .
C17 C 0.6974(4) 0.0189(3) 0.1292(3) 0.0217(8) Uani 1 1 d .
C18 C 0.5972(4) -0.0808(4) 0.0703(3) 0.0240(9) Uani 1 1 d .
C19 C 0.5887(4) -0.1950(4) -0.0281(3) 0.0288(10) Uani 1 1 d .
H19A H 0.6574 -0.2209 -0.0678 0.035 Uiso 1 1 calc R
C20 C 0.4772(4) -0.2682(4) -0.0651(3) 0.0310(10) Uani 1 1 d .
H20A H 0.4695 -0.3468 -0.1307 0.037 Uiso 1 1 calc R
C21 C 0.3745(4) -0.2296(4) -0.0083(3) 0.0305(10) Uani 1 1 d .
H21A H 0.2995 -0.2834 -0.0356 0.037 Uiso 1 1 calc R
C22 C 0.3801(4) -0.1158(4) 0.0856(4) 0.0291(10) Uani 1 1 d .
H22A H 0.3095 -0.0888 0.1218 0.035 Uiso 1 1 calc R
C23 C 0.4921(4) -0.0412(4) 0.1264(3) 0.0249(9) Uani 1 1 d .
C24 C 0.5298(3) 0.0841(4) 0.2185(3) 0.0215(8) Uani 1 1 d .
C25 C 0.8618(3) 0.1280(4) 0.3910(3) 0.0214(8) Uani 1 1 d .
C26 C 0.9856(4) 0.1605(4) 0.3903(3) 0.0220(8) Uani 1 1 d .
C27 C 1.0667(3) 0.0676(4) 0.3591(3) 0.0237(9) Uani 1 1 d .
C28 C 1.0257(3) -0.0554(4) 0.3385(3) 0.0235(9) Uani 1 1 d .
C29 C 0.9049(3) -0.0876(4) 0.3488(3) 0.0223(8) Uani 1 1 d .
C30 C 0.8244(3) 0.0057(4) 0.3756(3) 0.0220(8) Uani 1 1 d .
B1 B 0.7268(4) 0.2248(4) 0.3065(4) 0.0223(10) Uani 1 1 d .
C1S C 0.5380(5) 0.5895(5) 0.1096(4) 0.0420(12) Uani 1 1 d .
H1S H 0.5644 0.6512 0.1849 0.050 Uiso 1 1 calc R
C2S C 0.6216(5) 0.5436(5) 0.0349(4) 0.0403(12) Uani 1 1 d .
H2SA H 0.7059 0.5736 0.0591 0.048 Uiso 1 1 calc R
C3S C 0.5853(5) 0.4545(5) -0.0752(4) 0.0444(13) Uani 1 1 d .
H3S H 0.6439 0.4237 -0.1266 0.053 Uiso 1 1 calc R
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'
O O 0.0106 0.0060 '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
C25 O1 B1 115.6(3) . .
C8 N1 C1 113.4(3) . .
C8 N1 B1 122.9(3) . .
C1 N1 B1 122.0(3) . .
C8 N2 C9 117.9(3) . .
C16 N3 C9 112.6(3) . .
C16 N3 B1 123.2(3) . .
C9 N3 B1 123.5(3) . .
C17 N4 C16 116.7(3) . .
C24 N5 C17 113.8(3) . .
C24 N5 B1 122.9(3) . .
C17 N5 B1 122.8(3) . .
C1 N6 C24 116.8(3) . .
N6 C1 N1 123.2(3) . .
N6 C1 C2 129.5(4) . .
N1 C1 C2 105.5(3) . .
C3 C2 C7 121.1(4) . .
C3 C2 C1 131.5(4) . .
C7 C2 C1 107.3(3) . .
C4 C3 C2 117.5(4) . .
C4 C3 H3A 121.2 . .
C2 C3 H3A 121.2 . .
C3 C4 C5 121.3(4) . .
C3 C4 H4A 119.3 . .
C5 C4 H4A 119.3 . .
C6 C5 C4 122.0(4) . .
C6 C5 H5A 119.0 . .
C4 C5 H5A 119.0 . .
C5 C6 C7 117.5(4) . .
C5 C6 H6A 121.2 . .
C7 C6 H6A 121.2 . .
C6 C7 C2 120.3(4) . .
C6 C7 C8 132.4(4) . .
C2 C7 C8 107.2(3) . .
N2 C8 N1 122.5(3) . .
N2 C8 C7 129.9(4) . .
N1 C8 C7 105.3(3) . .
N2 C9 N3 121.2(3) . .
N2 C9 C10 131.2(4) . .
N3 C9 C10 106.2(3) . .
C11 C10 C15 119.7(4) . .
C11 C10 C9 133.7(4) . .
C15 C10 C9 106.4(3) . .
C10 C11 C12 118.9(4) . .
C10 C11 H11A 120.5 . .
C12 C11 H11A 120.5 . .
C11 C12 C13 121.7(4) . .
C11 C12 H12A 119.1 . .
C13 C12 H12A 119.1 . .
C14 C13 C12 120.7(4) . .
C14 C13 H13A 119.7 . .
C12 C13 H13A 119.7 . .
C13 C14 C15 118.7(4) . .
C13 C14 H14A 120.6 . .
C15 C14 H14A 120.6 . .
C14 C15 C10 120.2(4) . .
C14 C15 C16 131.9(4) . .
C10 C15 C16 107.8(3) . .
N4 C16 N3 122.0(3) . .
N4 C16 C15 130.7(3) . .
N3 C16 C15 105.6(3) . .
N4 C17 N5 122.7(3) . .
N4 C17 C18 130.6(3) . .
N5 C17 C18 105.1(3) . .
C19 C18 C23 120.5(4) . .
C19 C18 C17 131.8(4) . .
C23 C18 C17 107.7(3) . .
C20 C19 C18 117.5(4) . .
C20 C19 H19A 121.2 . .
C18 C19 H19A 121.2 . .
C19 C20 C21 121.7(4) . .
C19 C20 H20A 119.1 . .
C21 C20 H20A 119.1 . .
C22 C21 C20 121.5(4) . .
C22 C21 H21A 119.3 . .
C20 C21 H21A 119.3 . .
C21 C22 C23 118.1(4) . .
C21 C22 H22A 121.0 . .
C23 C22 H22A 121.0 . .
C22 C23 C18 120.7(4) . .
C22 C23 C24 132.8(4) . .
C18 C23 C24 106.4(3) . .
N5 C24 N6 122.4(3) . .
N5 C24 C23 106.2(3) . .
N6 C24 C23 129.8(3) . .
O1 C25 C30 121.6(3) . .
O1 C25 C26 120.0(3) . .
C30 C25 C26 118.4(3) . .
C25 C26 C27 120.7(4) . .
C25 C26 Br1 118.3(3) . .
C27 C26 Br1 121.1(3) . .
C28 C27 C26 119.4(4) . .
C28 C27 Br2 121.4(3) . .
C26 C27 Br2 119.1(3) . .
C27 C28 C29 120.8(3) . .
C27 C28 Br3 119.7(3) . .
C29 C28 Br3 119.5(3) . .
C28 C29 C30 118.6(4) . .
C28 C29 Br4 121.0(3) . .
C30 C29 Br4 120.3(3) . .
C25 C30 C29 121.6(4) . .
C25 C30 Br5 118.0(3) . .
C29 C30 Br5 120.5(3) . .
O1 B1 N3 116.7(3) . .
O1 B1 N1 111.6(3) . .
N3 B1 N1 104.5(3) . .
O1 B1 N5 114.9(4) . .
N3 B1 N5 103.1(3) . .
N1 B1 N5 104.7(3) . .
C2S C1S C3S 119.9(4) . 2_665
C2S C1S H1S 120.0 . .
C3S C1S H1S 120.0 2_665 .
C1S C2S C3S 121.0(5) . .
C1S C2S H2SA 119.5 . .
C3S C2S H2SA 119.5 . .
C2S C3S C1S 119.0(5) . 2_665
C2S C3S H3S 120.5 . .
C1S C3S H3S 120.5 2_665 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C26 1.890(4) .
Br2 C27 1.887(4) .
Br3 C28 1.899(4) .
Br4 C29 1.884(4) .
Br5 C30 1.897(4) .
O1 C25 1.365(4) .
O1 B1 1.468(6) .
N1 C8 1.365(5) .
N1 C1 1.370(5) .
N1 B1 1.492(5) .
N2 C8 1.343(5) .
N2 C9 1.347(5) .
N3 C16 1.372(5) .
N3 C9 1.379(5) .
N3 B1 1.483(6) .
N4 C17 1.340(5) .
N4 C16 1.355(5) .
N5 C24 1.349(5) .
N5 C17 1.367(4) .
N5 B1 1.501(5) .
N6 C1 1.345(5) .
N6 C24 1.352(5) .
C1 C2 1.456(5) .
C2 C3 1.394(5) .
C2 C7 1.420(5) .
C3 C4 1.392(6) .
C3 H3A 0.9500 .
C4 C5 1.392(6) .
C4 H4A 0.9500 .
C5 C6 1.384(6) .
C5 H5A 0.9500 .
C6 C7 1.405(6) .
C6 H6A 0.9500 .
C7 C8 1.460(5) .
C9 C10 1.445(5) .
C10 C11 1.374(6) .
C10 C15 1.438(5) .
C11 C12 1.380(6) .
C11 H11A 0.9500 .
C12 C13 1.397(6) .
C12 H12A 0.9500 .
C13 C14 1.370(6) .
C13 H13A 0.9500 .
C14 C15 1.397(5) .
C14 H14A 0.9500 .
C15 C16 1.444(6) .
C17 C18 1.451(5) .
C18 C19 1.401(5) .
C18 C23 1.425(6) .
C19 C20 1.376(6) .
C19 H19A 0.9500 .
C20 C21 1.404(6) .
C20 H20A 0.9500 .
C21 C22 1.372(6) .
C21 H21A 0.9500 .
C22 C23 1.388(6) .
C22 H22A 0.9500 .
C23 C24 1.455(5) .
C25 C30 1.388(6) .
C25 C26 1.397(5) .
C26 C27 1.401(5) .
C27 C28 1.384(6) .
C28 C29 1.397(5) .
C29 C30 1.400(5) .
C1S C2S 1.371(7) .
C1S C3S 1.389(7) 2_665
C1S H1S 0.9500 .
C2S C3S 1.381(7) .
C2S H2SA 0.9500 .
C3S C1S 1.389(7) 2_665
C3S H3S 0.9500 .
