#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:20:13 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180388 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/57/7205791.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_7205791
loop_
_publ_author_name
'Paton, Andrew S.'
'Lough, Alan J.'
'Bender, Timothy P.'
_publ_section_title
;
 A role for π--Br interactions in the solid-state molecular packing of
 para-halo-phenoxy-boronsubphthalocyanines
;
_journal_issue                   11
_journal_name_full               CrystEngComm
_journal_page_first              3653
_journal_paper_doi               10.1039/c0ce00796j
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C30 H16 B Br N6 O'
_chemical_formula_sum            'C30 H16 B Br N6 O'
_chemical_formula_weight         567.21
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 113.281(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.7312(12)
_cell_length_b                   10.2246(9)
_cell_length_c                   16.4141(13)
_cell_measurement_reflns_used    14248
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.7
_cell_volume                     2425.2(4)
_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(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.976
_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  0.0961
_diffrn_reflns_av_sigmaI/netI    0.1085
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            14248
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         2.70
_exptl_absorpt_coefficient_mu    1.734
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.311
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements
Sortav (Blessing 1995)
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1144
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.732
_refine_diff_density_min         -1.060
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         5448
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.1368
_refine_ls_R_factor_gt           0.0638
_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)+(0.0645P)²+0.8837P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1388
_refine_ls_wR_factor_ref         0.1690
_reflns_number_gt                2951
_reflns_number_total             5448
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c0ce00796j.txt
_cod_data_source_block           aBrPhO-BsubPc
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_cell_volume        2425.2(3)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7205791
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.13969(4) 0.02039(5) 0.09895(4) 0.0636(2) Uani 1 1 d . . .
O1 O 0.1731(2) 0.0479(3) 0.4599(2) 0.0434(8) Uani 1 1 d . . .
N1 N 0.2374(2) 0.1880(3) 0.5891(2) 0.0327(8) Uani 1 1 d . . .
N2 N 0.3907(2) 0.1093(3) 0.6605(2) 0.0365(8) Uani 1 1 d . . .
N3 N 0.3278(2) 0.1562(3) 0.5051(2) 0.0341(8) Uani 1 1 d . . .
N4 N 0.3088(2) 0.3053(3) 0.3883(2) 0.0365(8) Uani 1 1 d . . .
N5 N 0.1939(2) 0.2885(3) 0.4486(2) 0.0325(8) Uani 1 1 d . . .
N6 N 0.1247(2) 0.3579(3) 0.5467(2) 0.0370(8) Uani 1 1 d . . .
C1 C 0.1796(3) 0.2736(4) 0.6069(3) 0.0352(10) Uani 1 1 d . . .
C2 C 0.2114(3) 0.2737(4) 0.7035(3) 0.0360(10) Uani 1 1 d . . .
C3 C 0.1813(3) 0.3430(4) 0.7605(3) 0.0428(11) Uani 1 1 d . . .
H3A H 0.1276 0.3963 0.7380 0.051 Uiso 1 1 calc R . .
C4 C 0.2323(4) 0.3315(4) 0.8508(3) 0.0490(13) Uani 1 1 d . . .
H4A H 0.2121 0.3765 0.8906 0.059 Uiso 1 1 calc R . .
C5 C 0.3124(4) 0.2560(4) 0.8852(3) 0.0521(13) Uani 1 1 d . . .
H5A H 0.3461 0.2513 0.9476 0.063 Uiso 1 1 calc R . .
C6 C 0.3438(3) 0.1871(4) 0.8288(3) 0.0461(12) Uani 1 1 d . . .
H6A H 0.3982 0.1351 0.8518 0.055 Uiso 1 1 calc R . .
C7 C 0.2927(3) 0.1973(4) 0.7385(3) 0.0364(10) Uani 1 1 d . . .
C8 C 0.3109(3) 0.1519(4) 0.6631(3) 0.0341(10) Uani 1 1 d . . .
C9 C 0.4000(3) 0.1207(4) 0.5828(3) 0.0360(10) Uani 1 1 d . . .
C10 C 0.4832(3) 0.1363(4) 0.5668(3) 0.0380(10) Uani 1 1 d . . .
C11 C 0.5760(3) 0.1145(4) 0.6227(3) 0.0452(12) Uani 1 1 d . . .
H11A H 0.5926 0.0762 0.6797 0.054 Uiso 1 1 calc R . .
C12 C 0.6425(3) 0.1510(5) 0.5915(3) 0.0512(13) Uani 1 1 d . . .
H12A H 0.7058 0.1345 0.6270 0.061 Uiso 1 1 calc R . .
C13 C 0.6190(4) 0.2108(5) 0.5101(4) 0.0520(13) Uani 1 1 d . . .
H13A H 0.6667 0.2358 0.4916 0.062 Uiso 1 1 calc R . .
C14 C 0.5270(3) 0.2356(4) 0.4542(3) 0.0450(12) Uani 1 1 d . . .
H14A H 0.5117 0.2781 0.3988 0.054 Uiso 1 1 calc R . .
C15 C 0.4582(3) 0.1957(4) 0.4826(3) 0.0381(10) Uani 1 1 d . . .
C16 C 0.3586(3) 0.2179(4) 0.4477(3) 0.0362(10) Uani 1 1 d . . .
C17 C 0.2297(3) 0.3466(4) 0.3937(3) 0.0344(10) Uani 1 1 d . . .
C18 C 0.1807(3) 0.4696(4) 0.3661(3) 0.0363(10) Uani 1 1 d . . .
C19 C 0.1887(3) 0.5698(4) 0.3120(3) 0.0398(11) Uani 1 1 d . . .
H19A H 0.2308 0.5628 0.2837 0.048 Uiso 1 1 calc R . .
C20 C 0.1340(3) 0.6792(4) 0.3006(3) 0.0429(11) Uani 1 1 d . . .
H20A H 0.1375 0.7481 0.2633 0.052 Uiso 1 1 calc R . .
C21 C 0.0734(3) 0.6895(4) 0.3437(3) 0.0460(12) Uani 1 1 d . . .
H21A H 0.0353 0.7649 0.3336 0.055 Uiso 1 1 calc R . .
C22 C 0.0670(3) 0.5943(4) 0.4001(3) 0.0412(11) Uani 1 1 d . . .
H22A H 0.0270 0.6045 0.4304 0.049 Uiso 1 1 calc R . .
C23 C 0.1214(3) 0.4818(4) 0.4116(3) 0.0347(10) Uani 1 1 d . . .
C24 C 0.1374(3) 0.3704(4) 0.4699(3) 0.0336(10) Uani 1 1 d . . .
C25 C 0.1032(3) 0.0462(4) 0.3778(3) 0.0345(10) Uani 1 1 d . . .
C26 C 0.0134(3) 0.0284(4) 0.3705(3) 0.0428(11) Uani 1 1 d . . .
H26A H 0.0012 0.0216 0.4226 0.051 Uiso 1 1 calc R . .
C27 C -0.0591(3) 0.0205(4) 0.2880(3) 0.0437(11) Uani 1 1 d . . .
H27A H -0.1207 0.0075 0.2830 0.052 Uiso 1 1 calc R . .
C28 C -0.0401(3) 0.0317(4) 0.2139(3) 0.0428(12) Uani 1 1 d . . .
C29 C 0.0474(3) 0.0517(4) 0.2188(3) 0.0439(11) Uani 1 1 d . . .
H29A H 0.0587 0.0602 0.1663 0.053 Uiso 1 1 calc R . .
C30 C 0.1196(3) 0.0595(5) 0.3013(3) 0.0437(11) Uani 1 1 d . . .
H30A H 0.1808 0.0741 0.3055 0.052 Uiso 1 1 calc R . .
B1 B 0.2294(3) 0.1629(5) 0.4962(3) 0.0353(11) Uani 1 1 d . . .
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
_geom_angle_publ_flag
C25 O1 B1 122.6(3) . . ?
C8 N1 C1 112.7(3) . . ?
C8 N1 B1 124.2(3) . . ?
C1 N1 B1 121.9(4) . . ?
C9 N2 C8 117.0(4) . . ?
C16 N3 C9 111.8(3) . . ?
C16 N3 B1 123.0(4) . . ?
C9 N3 B1 122.9(3) . . ?
C16 N4 C17 117.1(4) . . ?
C24 N5 C17 112.4(3) . . ?
C24 N5 B1 122.8(3) . . ?
C17 N5 B1 123.4(3) . . ?
C1 N6 C24 117.2(3) . . ?
N6 C1 N1 122.8(4) . . ?
N6 C1 C2 130.1(4) . . ?
N1 C1 C2 105.0(4) . . ?
C3 C2 C7 120.0(4) . . ?
C3 C2 C1 131.7(4) . . ?
C7 C2 C1 107.9(4) . . ?
C4 C3 C2 117.9(4) . . ?
C3 C4 C5 122.0(4) . . ?
C4 C5 C6 120.7(5) . . ?
C7 C6 C5 117.6(4) . . ?
C6 C7 C2 121.8(4) . . ?
C6 C7 C8 131.5(4) . . ?
C2 C7 C8 106.4(4) . . ?
N2 C8 N1 122.5(4) . . ?
N2 C8 C7 129.1(4) . . ?
N1 C8 C7 106.9(3) . . ?
N2 C9 N3 122.8(4) . . ?
N2 C9 C10 129.0(4) . . ?
N3 C9 C10 106.1(3) . . ?
C11 C10 C15 121.6(4) . . ?
C11 C10 C9 130.4(4) . . ?
C15 C10 C9 107.6(4) . . ?
C12 C11 C10 117.3(4) . . ?
C13 C12 C11 121.6(5) . . ?
C12 C13 C14 121.9(5) . . ?
C13 C14 C15 117.8(4) . . ?
C14 C15 C10 119.8(4) . . ?
C14 C15 C16 132.6(4) . . ?
C10 C15 C16 107.0(4) . . ?
N4 C16 N3 123.2(4) . . ?
N4 C16 C15 128.7(4) . . ?
N3 C16 C15 106.0(4) . . ?
N4 C17 N5 122.4(4) . . ?
N4 C17 C18 129.9(4) . . ?
N5 C17 C18 106.0(3) . . ?
C19 C18 C23 121.1(4) . . ?
C19 C18 C17 131.7(4) . . ?
C23 C18 C17 107.0(4) . . ?
C20 C19 C18 118.3(4) . . ?
C19 C20 C21 120.4(4) . . ?
C22 C21 C20 122.3(4) . . ?
C21 C22 C23 118.0(4) . . ?
C22 C23 C18 119.8(4) . . ?
C22 C23 C24 132.4(4) . . ?
C18 C23 C24 107.6(3) . . ?
N6 C24 N5 122.1(4) . . ?
N6 C24 C23 129.7(4) . . ?
N5 C24 C23 105.9(3) . . ?
O1 C25 C26 119.0(4) . . ?
O1 C25 C30 122.0(4) . . ?
C26 C25 C30 119.0(4) . . ?
C25 C26 C27 120.7(4) . . ?
C28 C27 C26 118.7(4) . . ?
C29 C28 C27 122.1(4) . . ?
C29 C28 Br1 118.7(4) . . ?
C27 C28 Br1 119.3(3) . . ?
C28 C29 C30 119.1(4) . . ?
C29 C30 C25 120.4(4) . . ?
O1 B1 N5 116.2(4) . . ?
O1 B1 N3 116.3(4) . . ?
N5 B1 N3 104.4(3) . . ?
O1 B1 N1 110.3(4) . . ?
N5 B1 N1 104.4(3) . . ?
N3 B1 N1 103.9(4) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C28 1.922(4) . ?
O1 C25 1.362(5) . ?
O1 B1 1.451(6) . ?
N1 C8 1.356(5) . ?
N1 C1 1.375(5) . ?
N1 B1 1.503(6) . ?
N2 C9 1.345(5) . ?
N2 C8 1.345(5) . ?
N3 C16 1.371(5) . ?
N3 C9 1.380(5) . ?
N3 B1 1.497(6) . ?
N4 C16 1.327(5) . ?
N4 C17 1.349(5) . ?
N5 C24 1.364(5) . ?
N5 C17 1.372(5) . ?
N5 B1 1.492(6) . ?
N6 C1 1.338(5) . ?
N6 C24 1.359(5) . ?
C1 C2 1.462(6) . ?
C2 C3 1.396(6) . ?
C2 C7 1.413(6) . ?
C3 C4 1.384(6) . ?
C4 C5 1.393(7) . ?
C5 C6 1.399(6) . ?
C6 C7 1.383(6) . ?
C7 C8 1.453(6) . ?
C9 C10 1.442(6) . ?
C10 C11 1.401(6) . ?
C10 C15 1.415(6) . ?
C11 C12 1.385(6) . ?
C12 C13 1.380(7) . ?
C13 C14 1.396(7) . ?
C14 C15 1.399(6) . ?
C15 C16 1.457(6) . ?
C17 C18 1.450(6) . ?
C18 C19 1.394(6) . ?
C18 C23 1.412(6) . ?
C19 C20 1.379(6) . ?
C20 C21 1.396(6) . ?
C21 C22 1.374(6) . ?
C22 C23 1.401(6) . ?
C23 C24 1.445(6) . ?
C25 C26 1.382(6) . ?
C25 C30 1.384(6) . ?
C26 C27 1.386(6) . ?
C27 C28 1.366(6) . ?
C28 C29 1.362(6) . ?
C29 C30 1.384(6) . ?
