#------------------------------------------------------------------------------
#$Date: 2016-03-26 18:23:59 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180427 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/96/7209614.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_7209614
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 H16 B I N6 O'
_chemical_formula_sum            'C30 H16 B I N6 O'
_chemical_formula_weight         614.20
_chemical_name_common            (2-Iodophenolato)(subphthalocyaninato)boron
_chemical_name_systematic
;
(2-Iodophenolato)(subphthalocyaninato)boron
;
_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                 112.710(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.0324(5)
_cell_length_b                   20.5587(8)
_cell_length_c                   11.6778(6)
_cell_measurement_reflns_used    15379
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      2.7
_cell_volume                     2443.3(2)
_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 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0920
_diffrn_reflns_av_sigmaI/netI    0.0867
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            15379
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.74
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.349
_exptl_absorpt_correction_T_max  0.900
_exptl_absorpt_correction_T_min  0.607
_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    1.670
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.627
_refine_diff_density_min         -1.298
_refine_diff_density_rms         0.147
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         4282
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.1609
_refine_ls_R_factor_gt           0.0914
_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)+(0.1655P)²+8.8640P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2426
_refine_ls_wR_factor_ref         0.3026
_reflns_number_gt                2315
_reflns_number_total             4282
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c3ce26711c.txt
_cod_data_source_block           k11175
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        2443.31(19)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7209614
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_group
I1 I -0.0014(5) 0.0741(3) 0.0322(4) 0.0719(13) Uani 0.432(10) 1 d PD 1
I1A I -0.0116(4) 0.1052(4) 0.0111(6) 0.1098(19) Uani 0.568(10) 1 d PD 2
O1 O 0.2603(5) 0.1320(2) 0.2413(5) 0.0388(13) Uani 1 1 d D .
N1 N 0.4890(6) 0.0963(3) 0.3202(6) 0.0301(15) Uani 1 1 d . .
N2 N 0.4653(6) -0.0158(3) 0.2664(6) 0.0332(15) Uani 1 1 d . .
N3 N 0.3538(6) 0.0658(3) 0.1180(6) 0.0335(15) Uani 1 1 d . .
N4 N 0.3285(6) 0.1370(3) -0.0497(6) 0.0334(15) Uani 1 1 d . .
N5 N 0.4213(6) 0.1747(3) 0.1588(5) 0.0298(15) Uani 1 1 d . .
N6 N 0.6041(6) 0.1974(3) 0.3475(6) 0.0345(16) Uani 1 1 d . .
C1 C 0.5893(8) 0.1381(4) 0.3876(7) 0.0318(18) Uani 1 1 d . .
C2 C 0.6821(8) 0.0972(4) 0.4855(7) 0.0323(18) Uani 1 1 d . .
C3 C 0.8004(8) 0.1122(4) 0.5811(7) 0.0351(19) Uani 1 1 d . .
H3A H 0.8312 0.1558 0.5959 0.042 Uiso 1 1 calc R .
C4 C 0.8725(8) 0.0618(4) 0.6546(8) 0.044(2) Uani 1 1 d . .
H4A H 0.9543 0.0708 0.7202 0.053 Uiso 1 1 calc R .
C5 C 0.8261(9) -0.0028(4) 0.6333(8) 0.042(2) Uani 1 1 d . .
H5A H 0.8752 -0.0364 0.6870 0.051 Uiso 1 1 calc R .
C6 C 0.7108(8) -0.0178(4) 0.5359(8) 0.038(2) Uani 1 1 d . .
H6A H 0.6812 -0.0616 0.5204 0.046 Uiso 1 1 calc R .
C7 C 0.6389(8) 0.0321(4) 0.4609(7) 0.0323(18) Uani 1 1 d . .
C8 C 0.5199(8) 0.0322(4) 0.3466(7) 0.0357(19) Uani 1 1 d . .
C9 C 0.3887(8) 0.0023(4) 0.1504(7) 0.0332(19) Uani 1 1 d . .
C10 C 0.3485(8) -0.0327(4) 0.0321(7) 0.0339(18) Uani 1 1 d . .
C11 C 0.3512(9) -0.0985(4) 0.0037(9) 0.043(2) Uani 1 1 d . .
H11A H 0.3868 -0.1299 0.0676 0.052 Uiso 1 1 calc R .
C12 C 0.3009(8) -0.1167(4) -0.1193(8) 0.043(2) Uani 1 1 d . .
H12A H 0.2988 -0.1615 -0.1398 0.052 Uiso 1 1 calc R .
C13 C 0.2525(8) -0.0704(4) -0.2156(8) 0.045(2) Uani 1 1 d . .
H13A H 0.2168 -0.0846 -0.2995 0.054 Uiso 1 1 calc R .
C14 C 0.2566(9) -0.0045(4) -0.1890(8) 0.042(2) Uani 1 1 d . .
H14A H 0.2289 0.0269 -0.2538 0.051 Uiso 1 1 calc R .
C15 C 0.3026(7) 0.0146(4) -0.0647(8) 0.0360(19) Uani 1 1 d . .
C16 C 0.3203(7) 0.0780(4) -0.0060(7) 0.0328(18) Uani 1 1 d . .
C17 C 0.3869(7) 0.1836(4) 0.0337(7) 0.0336(19) Uani 1 1 d . .
C18 C 0.4580(7) 0.2426(4) 0.0216(7) 0.0312(17) Uani 1 1 d . .
C19 C 0.4581(8) 0.2756(4) -0.0796(7) 0.0362(19) Uani 1 1 d . .
H19A H 0.4025 0.2629 -0.1612 0.043 Uiso 1 1 calc R .
C20 C 0.5424(9) 0.3285(4) -0.0592(8) 0.045(2) Uani 1 1 d . .
H20A H 0.5432 0.3528 -0.1280 0.055 Uiso 1 1 calc R .
C21 C 0.6260(8) 0.3465(4) 0.0611(8) 0.041(2) Uani 1 1 d . .
H21A H 0.6827 0.3828 0.0720 0.049 Uiso 1 1 calc R .
C22 C 0.6284(8) 0.3128(4) 0.1646(7) 0.0349(19) Uani 1 1 d . .
H22A H 0.6867 0.3245 0.2459 0.042 Uiso 1 1 calc R .
C23 C 0.5414(7) 0.2610(3) 0.1440(7) 0.0316(18) Uani 1 1 d . .
C24 C 0.5248(8) 0.2139(3) 0.2312(7) 0.0321(18) Uani 1 1 d . .
C25 C 0.1685(11) 0.1808(4) 0.1945(16) 0.0526(14) Uani 0.432(10) 1 d PGD 1
C26 C 0.0435(10) 0.1648(5) 0.1101(13) 0.0526(14) Uani 0.432(10) 1 d PGD 1
C27 C -0.0522(9) 0.2128(6) 0.0657(13) 0.0526(14) Uani 0.432(10) 1 d PGD 1
H27A H -0.1377 0.2018 0.0080 0.063 Uiso 0.432(10) 1 calc PR 1
C28 C -0.0228(11) 0.2767(5) 0.1055(14) 0.0526(14) Uani 0.432(10) 1 d PG 1
H28A H -0.0882 0.3095 0.0751 0.063 Uiso 0.432(10) 1 calc PR 1
C29 C 0.1023(13) 0.2927(4) 0.1898(14) 0.0526(14) Uani 0.432(10) 1 d PG 1
H29A H 0.1223 0.3364 0.2170 0.063 Uiso 0.432(10) 1 calc PR 1
C30 C 0.1979(11) 0.2447(4) 0.2343(15) 0.0526(14) Uani 0.432(10) 1 d PG 1
H30A H 0.2834 0.2556 0.2919 0.063 Uiso 0.432(10) 1 calc PR 1
C25A C 0.1910(9) 0.1892(3) 0.2042(12) 0.0526(14) Uani 0.568(10) 1 d PGD 2
C26A C 0.0620(8) 0.1861(4) 0.1183(10) 0.0526(14) Uani 0.568(10) 1 d PGD 2
C27A C -0.0175(8) 0.2410(5) 0.0936(10) 0.0526(14) Uani 0.568(10) 1 d PGD 2
H27B H -0.1056 0.2389 0.0349 0.063 Uiso 0.568(10) 1 calc PR 2
C28A C 0.0320(10) 0.2990(4) 0.1549(11) 0.0526(14) Uani 0.568(10) 1 d PG 2
H28B H -0.0224 0.3366 0.1380 0.063 Uiso 0.568(10) 1 calc PR 2
C29A C 0.1609(11) 0.3022(3) 0.2408(11) 0.0526(14) Uani 0.568(10) 1 d PG 2
H29B H 0.1947 0.3419 0.2827 0.063 Uiso 0.568(10) 1 calc PR 2
C30A C 0.2404(9) 0.2473(4) 0.2655(12) 0.0526(14) Uani 0.568(10) 1 d PG 2
H30B H 0.3285 0.2494 0.3242 0.063 Uiso 0.568(10) 1 calc PR 2
B1 B 0.3726(9) 0.1182(4) 0.2110(8) 0.033(2) 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'
I I -0.4742 1.8119 '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'
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_3
C26 I1 I1 164.9(3) 3
C25A O1 C25 12.0(6) .
C25A O1 B1 121.1(8) .
C25 O1 B1 127.9(11) .
C8 N1 C1 113.3(6) .
C8 N1 B1 122.9(6) .
C1 N1 B1 122.5(6) .
C8 N2 C9 116.1(6) .
C16 N3 C9 113.4(6) .
C16 N3 B1 122.9(6) .
C9 N3 B1 122.9(7) .
C16 N4 C17 117.2(6) .
C17 N5 C24 113.3(6) .
C17 N5 B1 122.6(6) .
C24 N5 B1 122.7(6) .
C1 N6 C24 117.5(6) .
N6 C1 N1 123.1(6) .
N6 C1 C2 130.6(7) .
N1 C1 C2 104.6(6) .
C3 C2 C7 120.9(7) .
C3 C2 C1 131.1(7) .
C7 C2 C1 107.8(7) .
C4 C3 C2 118.1(7) .
C4 C3 H3A 121.0 .
C2 C3 H3A 121.0 .
C3 C4 C5 120.9(8) .
C3 C4 H4A 119.6 .
C5 C4 H4A 119.6 .
C6 C5 C4 121.0(8) .
C6 C5 H5A 119.5 .
C4 C5 H5A 119.5 .
C5 C6 C7 118.5(8) .
C5 C6 H6A 120.7 .
C7 C6 H6A 120.7 .
C6 C7 C2 120.6(7) .
C6 C7 C8 132.0(7) .
C2 C7 C8 107.3(7) .
N2 C8 N1 123.4(7) .
N2 C8 C7 129.8(7) .
N1 C8 C7 105.3(7) .
N2 C9 N3 122.8(7) .
N2 C9 C10 131.1(7) .
N3 C9 C10 104.9(7) .
C11 C10 C15 120.4(8) .
C11 C10 C9 132.3(8) .
C15 C10 C9 107.2(6) .
C12 C11 C10 118.3(8) .
C12 C11 H11A 120.8 .
C10 C11 H11A 120.8 .
C11 C12 C13 121.6(8) .
C11 C12 H12A 119.2 .
C13 C12 H12A 119.2 .
C14 C13 C12 120.8(8) .
C14 C13 H13A 119.6 .
C12 C13 H13A 119.6 .
C13 C14 C15 118.3(8) .
C13 C14 H14A 120.8 .
C15 C14 H14A 120.8 .
C14 C15 C10 120.4(7) .
C14 C15 C16 132.3(8) .
C10 C15 C16 107.3(7) .
N4 C16 N3 122.6(7) .
N4 C16 C15 130.8(7) .
N3 C16 C15 105.5(6) .
N4 C17 N5 122.4(7) .
N4 C17 C18 129.8(7) .
N5 C17 C18 105.7(6) .
C19 C18 C23 121.5(7) .
C19 C18 C17 132.0(7) .
C23 C18 C17 106.5(7) .
C18 C19 C20 117.8(7) .
C18 C19 H19A 121.1 .
C20 C19 H19A 121.1 .
C19 C20 C21 121.1(8) .
C19 C20 H20A 119.4 .
C21 C20 H20A 119.4 .
C22 C21 C20 121.8(8) .
C22 C21 H21A 119.1 .
C20 C21 H21A 119.1 .
C21 C22 C23 116.9(7) .
C21 C22 H22A 121.5 .
C23 C22 H22A 121.5 .
C22 C23 C18 120.9(7) .
C22 C23 C24 130.4(7) .
C18 C23 C24 108.4(6) .
N6 C24 N5 122.1(7) .
N6 C24 C23 131.3(7) .
N5 C24 C23 104.8(6) .
O1 C25 C26 119.0(6) .
O1 C25 C30 120.9(6) .
C26 C25 C30 120.0 .
C25 C26 C27 120.0 .
C25 C26 I1 122.2(4) .
C27 C26 I1 117.5(4) .
C26 C27 C28 120.0 .
C26 C27 H27A 120.0 .
C28 C27 H27A 120.0 .
C29 C28 C27 120.0 .
C29 C28 H28A 120.0 .
C27 C28 H28A 120.0 .
C28 C29 C30 120.0 .
C28 C29 H29A 120.0 .
C30 C29 H29A 120.0 .
C29 C30 C25 120.0 .
C29 C30 H30A 120.0 .
C25 C30 H30A 120.0 .
O1 C25A C26A 118.5(6) .
O1 C25A C30A 120.7(6) .
C26A C25A C30A 120.0 .
C25A C26A C27A 120.0 .
C25A C26A I1A 122.1(4) .
C27A C26A I1A 117.5(4) .
C26A C27A C28A 120.0 .
C26A C27A H27B 120.0 .
C28A C27A H27B 120.0 .
C29A C28A C27A 120.0 .
C29A C28A H28B 120.0 .
C27A C28A H28B 120.0 .
C30A C29A C28A 120.0 .
C30A C29A H29B 120.0 .
C28A C29A H29B 120.0 .
C29A C30A C25A 120.0 .
C29A C30A H30B 120.0 .
C25A C30A H30B 120.0 .
O1 B1 N3 115.5(7) .
O1 B1 N1 112.8(7) .
N3 B1 N1 103.7(6) .
O1 B1 N5 115.0(7) .
N3 B1 N5 103.6(7) .
N1 B1 N5 104.8(6) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1 C26 2.051(7) .
I1 I1 3.141(13) 3
I1A C26A 2.050(7) .
O1 C25A 1.378(7) .
O1 C25 1.379(7) .
O1 B1 1.442(11) .
N1 C8 1.366(10) .
N1 C1 1.381(10) .
N1 B1 1.488(11) .
N2 C8 1.334(10) .
N2 C9 1.343(10) .
N3 C16 1.372(10) .
N3 C9 1.372(10) .
N3 B1 1.487(11) .
N4 C16 1.333(10) .
N4 C17 1.339(10) .
N5 C17 1.373(10) .
N5 C24 1.386(10) .
N5 B1 1.503(11) .
N6 C1 1.339(9) .
N6 C24 1.344(9) .
C1 C2 1.469(10) .
C2 C3 1.386(11) .
C2 C7 1.412(11) .
C3 C4 1.384(11) .
C3 H3A 0.9500 .
C4 C5 1.409(12) .
C4 H4A 0.9500 .
C5 C6 1.375(12) .
C5 H5A 0.9500 .
C6 C7 1.384(11) .
C6 H6A 0.9500 .
C7 C8 1.467(11) .
C9 C10 1.467(11) .
C10 C11 1.395(11) .
C10 C15 1.429(12) .
C11 C12 1.377(12) .
C11 H11A 0.9500 .
C12 C13 1.411(13) .
C12 H12A 0.9500 .
C13 C14 1.388(12) .
C13 H13A 0.9500 .
C14 C15 1.397(12) .
C14 H14A 0.9500 .
C15 C16 1.449(11) .
C17 C18 1.481(11) .
C18 C19 1.363(11) .
C18 C23 1.421(10) .
C19 C20 1.390(12) .
C19 H19A 0.9500 .
C20 C21 1.401(12) .
C20 H20A 0.9500 .
C21 C22 1.384(11) .
C21 H21A 0.9500 .
C22 C23 1.391(11) .
C22 H22A 0.9500 .
C23 C24 1.468(11) .
C25 C26 1.3900 .
C25 C30 1.3900 .
C26 C27 1.3900 .
C27 C28 1.3900 .
C27 H27A 0.9500 .
C28 C29 1.3900 .
C28 H28A 0.9500 .
C29 C30 1.3900 .
C29 H29A 0.9500 .
C30 H30A 0.9500 .
C25A C26A 1.3900 .
C25A C30A 1.3900 .
C26A C27A 1.3900 .
C27A C28A 1.3900 .
C27A H27B 0.9500 .
C28A C29A 1.3900 .
C28A H28B 0.9500 .
C29A C30A 1.3900 .
C29A H29B 0.9500 .
C30A H30B 0.9500 .
