#------------------------------------------------------------------------------
#$Date: 2016-03-26 18:23:59 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180427 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/96/7209613.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_7209613
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, 0.5(C6 H6)'
_chemical_formula_sum            'C33 H19 B I N6 O'
_chemical_formula_weight         653.25
_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                 97.6040(16)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.1641(3)
_cell_length_b                   13.8900(4)
_cell_length_c                   19.3994(6)
_cell_measurement_reflns_used    18456
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.6
_cell_volume                     2714.71(14)
_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 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0488
_diffrn_reflns_av_sigmaI/netI    0.0618
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            18456
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.58
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.220
_exptl_absorpt_correction_T_max  0.890
_exptl_absorpt_correction_T_min  0.789
_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    1.598
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1300
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.477
_refine_diff_density_min         -1.098
_refine_diff_density_rms         0.123
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         6189
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0840
_refine_ls_R_factor_gt           0.0479
_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)+(0.0537P)²+6.6201P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1127
_refine_ls_wR_factor_ref         0.1317
_reflns_number_gt                4276
_reflns_number_total             6189
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c3ce26711c.txt
_cod_data_source_block           k11197
_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_sg_symbol_H-M      'P 21/n'
_cod_database_code               7209613
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
I1 I 0.46821(3) 0.12654(2) 0.089835(16) 0.03212(12) Uani 1 1 d .
O1 O 0.7599(3) 0.0968(2) 0.17622(14) 0.0211(6) Uani 1 1 d .
N1 N 0.6921(3) -0.1205(2) 0.06693(17) 0.0190(7) Uani 1 1 d .
N2 N 0.8723(3) -0.0388(2) 0.13195(17) 0.0186(7) Uani 1 1 d .
N3 N 1.0803(4) -0.0335(2) 0.20476(18) 0.0228(8) Uani 1 1 d .
N4 N 0.8768(3) -0.0297(2) 0.25327(17) 0.0194(7) Uani 1 1 d .
N5 N 0.7030(4) -0.1023(3) 0.30590(17) 0.0223(8) Uani 1 1 d .
N6 N 0.6789(3) -0.0717(2) 0.18359(17) 0.0194(7) Uani 1 1 d .
C1 C 0.8159(4) -0.0867(3) 0.0732(2) 0.0198(9) Uani 1 1 d .
C2 C 0.9264(4) -0.1093(3) 0.0353(2) 0.0218(9) Uani 1 1 d .
C3 C 0.9326(5) -0.1536(3) -0.0287(2) 0.0246(9) Uani 1 1 d .
H3A H 0.8541 -0.1745 -0.0569 0.030 Uiso 1 1 calc R
C4 C 1.0560(5) -0.1663(3) -0.0502(2) 0.0297(11) Uani 1 1 d .
H4A H 1.0614 -0.1945 -0.0943 0.036 Uiso 1 1 calc R
C5 C 1.1723(5) -0.1389(3) -0.0088(2) 0.0277(10) Uani 1 1 d .
H5A H 1.2552 -0.1483 -0.0254 0.033 Uiso 1 1 calc R
C6 C 1.1695(5) -0.0982(3) 0.0560(2) 0.0256(10) Uani 1 1 d .
H6A H 1.2492 -0.0824 0.0851 0.031 Uiso 1 1 calc R
C7 C 1.0449(4) -0.0811(3) 0.0775(2) 0.0224(9) Uani 1 1 d .
C8 C 1.0074(4) -0.0428(3) 0.1417(2) 0.0207(9) Uani 1 1 d .
C9 C 1.0129(4) -0.0330(3) 0.2597(2) 0.0216(9) Uani 1 1 d .
C10 C 1.0567(4) -0.0571(3) 0.3325(2) 0.0220(9) Uani 1 1 d .
C11 C 1.1821(5) -0.0678(3) 0.3693(2) 0.0297(10) Uani 1 1 d .
H11A H 1.2595 -0.0581 0.3475 0.036 Uiso 1 1 calc R
C12 C 1.1913(5) -0.0931(4) 0.4387(3) 0.0364(12) Uani 1 1 d .
H12A H 1.2762 -0.0989 0.4655 0.044 Uiso 1 1 calc R
C13 C 1.0774(5) -0.1102(4) 0.4699(2) 0.0357(12) Uani 1 1 d .
H13A H 1.0871 -0.1268 0.5178 0.043 Uiso 1 1 calc R
C14 C 0.9512(5) -0.1039(3) 0.4337(2) 0.0303(11) Uani 1 1 d .
H14A H 0.8747 -0.1178 0.4552 0.036 Uiso 1 1 calc R
C15 C 0.9410(4) -0.0764(3) 0.3639(2) 0.0229(9) Uani 1 1 d .
C16 C 0.8265(4) -0.0667(3) 0.3099(2) 0.0228(9) Uani 1 1 d .
C17 C 0.6348(4) -0.1102(3) 0.2418(2) 0.0200(9) Uani 1 1 d .
C18 C 0.5281(4) -0.1756(3) 0.2159(2) 0.0214(9) Uani 1 1 d .
C19 C 0.4484(5) -0.2363(3) 0.2497(2) 0.0291(10) Uani 1 1 d .
H19A H 0.4500 -0.2334 0.2987 0.035 Uiso 1 1 calc R
C20 C 0.3666(5) -0.3011(3) 0.2101(3) 0.0330(11) Uani 1 1 d .
H20A H 0.3119 -0.3431 0.2326 0.040 Uiso 1 1 calc R
C21 C 0.3628(4) -0.3062(3) 0.1382(3) 0.0315(11) Uani 1 1 d .
H21A H 0.3054 -0.3512 0.1125 0.038 Uiso 1 1 calc R
C22 C 0.4418(4) -0.2463(3) 0.1034(2) 0.0258(10) Uani 1 1 d .
H22A H 0.4390 -0.2501 0.0544 0.031 Uiso 1 1 calc R
C23 C 0.5249(4) -0.1807(3) 0.1420(2) 0.0212(9) Uani 1 1 d .
C24 C 0.6289(4) -0.1190(3) 0.1239(2) 0.0188(8) Uani 1 1 d .
C25 C 0.6780(4) 0.1380(3) 0.2179(2) 0.0196(9) Uani 1 1 d .
C26 C 0.5462(4) 0.1606(3) 0.1920(2) 0.0241(9) Uani 1 1 d .
C27 C 0.4643(5) 0.2057(3) 0.2345(3) 0.0305(11) Uani 1 1 d .
H27A H 0.3756 0.2219 0.2162 0.037 Uiso 1 1 calc R
C28 C 0.5111(5) 0.2271(3) 0.3028(3) 0.0359(12) Uani 1 1 d .
H28A H 0.4546 0.2568 0.3318 0.043 Uiso 1 1 calc R
C29 C 0.6400(5) 0.2051(3) 0.3285(2) 0.0330(11) Uani 1 1 d .
H29A H 0.6722 0.2199 0.3755 0.040 Uiso 1 1 calc R
C30 C 0.7245(5) 0.1614(3) 0.2869(2) 0.0262(10) Uani 1 1 d .
H30A H 0.8137 0.1476 0.3054 0.031 Uiso 1 1 calc R
B1 B 0.7935(5) -0.0035(3) 0.1865(2) 0.0192(10) Uani 1 1 d .
C1S C 0.5576(5) -0.0693(4) 0.4626(3) 0.0329(11) Uani 1 1 d .
H1S H 0.5984 -0.1166 0.4370 0.039 Uiso 1 1 calc R
C2S C 0.5201(5) 0.0179(4) 0.4321(2) 0.0311(11) Uani 1 1 d .
H2S H 0.5327 0.0298 0.3852 0.037 Uiso 1 1 calc R
C3S C 0.4640(5) 0.0881(4) 0.4696(2) 0.0312(11) Uani 1 1 d .
H3S H 0.4405 0.1488 0.4490 0.037 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'
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_1
_geom_angle_site_symmetry_3
C25 O1 B1 118.5(3) . .
C1 N1 C24 117.7(3) . .
C8 N2 C1 113.3(3) . .
C8 N2 B1 122.7(3) . .
C1 N2 B1 122.8(4) . .
C9 N3 C8 116.3(4) . .
C16 N4 C9 113.1(3) . .
C16 N4 B1 123.8(4) . .
C9 N4 B1 122.3(3) . .
C16 N5 C17 116.5(3) . .
C24 N6 C17 112.5(3) . .
C24 N6 B1 122.3(3) . .
C17 N6 B1 123.5(3) . .
N1 C1 N2 122.0(4) . .
N1 C1 C2 131.2(4) . .
N2 C1 C2 105.0(4) . .
C3 C2 C7 120.1(4) . .
C3 C2 C1 132.4(4) . .
C7 C2 C1 107.5(4) . .
C4 C3 C2 118.2(4) . .
C4 C3 H3A 120.9 . .
C2 C3 H3A 120.9 . .
C3 C4 C5 121.8(4) . .
C3 C4 H4A 119.1 . .
C5 C4 H4A 119.1 . .
C6 C5 C4 121.2(4) . .
C6 C5 H5A 119.4 . .
C4 C5 H5A 119.4 . .
C5 C6 C7 117.9(4) . .
C5 C6 H6A 121.1 . .
C7 C6 H6A 121.1 . .
C6 C7 C2 120.8(4) . .
C6 C7 C8 131.8(4) . .
C2 C7 C8 107.3(4) . .
N3 C8 N2 122.9(4) . .
N3 C8 C7 129.6(4) . .
N2 C8 C7 105.7(4) . .
N3 C9 N4 122.9(4) . .
N3 C9 C10 130.1(4) . .
N4 C9 C10 105.6(4) . .
C11 C10 C15 121.1(4) . .
C11 C10 C9 131.6(4) . .
C15 C10 C9 107.1(4) . .
C12 C11 C10 117.9(5) . .
C12 C11 H11A 121.0 . .
C10 C11 H11A 121.0 . .
C11 C12 C13 120.9(4) . .
C11 C12 H12A 119.6 . .
C13 C12 H12A 119.6 . .
C14 C13 C12 122.4(4) . .
C14 C13 H13A 118.8 . .
C12 C13 H13A 118.8 . .
C13 C14 C15 117.1(5) . .
C13 C14 H14A 121.5 . .
C15 C14 H14A 121.5 . .
C14 C15 C10 120.6(4) . .
C14 C15 C16 131.9(4) . .
C10 C15 C16 107.5(4) . .
N5 C16 N4 122.5(4) . .
N5 C16 C15 131.0(4) . .
N4 C16 C15 105.2(4) . .
N5 C17 N6 122.8(4) . .
N5 C17 C18 129.8(4) . .
N6 C17 C18 105.6(3) . .
C19 C18 C23 120.2(4) . .
C19 C18 C17 132.1(4) . .
C23 C18 C17 107.1(4) . .
C20 C19 C18 118.5(4) . .
C20 C19 H19A 120.8 . .
C18 C19 H19A 120.8 . .
C19 C20 C21 121.5(4) . .
C19 C20 H20A 119.3 . .
C21 C20 H20A 119.3 . .
C22 C21 C20 121.0(4) . .
C22 C21 H21A 119.5 . .
C20 C21 H21A 119.5 . .
C23 C22 C21 118.6(4) . .
C23 C22 H22A 120.7 . .
C21 C22 H22A 120.7 . .
C22 C23 C18 120.2(4) . .
C22 C23 C24 132.2(4) . .
C18 C23 C24 107.1(4) . .
N1 C24 N6 122.5(4) . .
N1 C24 C23 129.3(4) . .
N6 C24 C23 106.4(3) . .
O1 C25 C30 120.8(4) . .
O1 C25 C26 120.8(4) . .
C30 C25 C26 118.4(4) . .
C27 C26 C25 120.4(4) . .
C27 C26 I1 118.7(3) . .
C25 C26 I1 120.9(3) . .
C28 C27 C26 120.4(4) . .
C28 C27 H27A 119.8 . .
C26 C27 H27A 119.8 . .
C29 C28 C27 119.5(4) . .
C29 C28 H28A 120.2 . .
C27 C28 H28A 120.2 . .
C28 C29 C30 121.2(5) . .
C28 C29 H29A 119.4 . .
C30 C29 H29A 119.4 . .
C29 C30 C25 120.0(4) . .
C29 C30 H30A 120.0 . .
C25 C30 H30A 120.0 . .
O1 B1 N2 111.1(3) . .
O1 B1 N4 116.8(4) . .
N2 B1 N4 103.9(3) . .
O1 B1 N6 115.9(4) . .
N2 B1 N6 104.7(3) . .
N4 B1 N6 103.1(3) . .
C2S C1S C3S 120.1(5) . 3_656
C2S C1S H1S 119.9 . .
C3S C1S H1S 119.9 3_656 .
C1S C2S C3S 120.2(4) . .
C1S C2S H2S 119.9 . .
C3S C2S H2S 119.9 . .
C2S C3S C1S 119.7(5) . 3_656
C2S C3S H3S 120.2 . .
C1S C3S H3S 120.2 3_656 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1 C26 2.090(4) .
O1 C25 1.361(5) .
O1 B1 1.442(6) .
N1 C1 1.334(5) .
N1 C24 1.351(5) .
N2 C8 1.363(5) .
N2 C1 1.377(5) .
N2 B1 1.491(6) .
N3 C9 1.340(6) .
N3 C8 1.350(5) .
N4 C16 1.371(5) .
N4 C9 1.373(5) .
N4 B1 1.496(6) .
N5 C16 1.342(6) .
N5 C17 1.346(5) .
N6 C24 1.368(5) .
N6 C17 1.376(5) .
N6 B1 1.497(6) .
C1 C2 1.456(6) .
C2 C3 1.394(6) .
C2 C7 1.419(6) .
C3 C4 1.384(6) .
C3 H3A 0.9500 .
C4 C5 1.391(7) .
C4 H4A 0.9500 .
C5 C6 1.382(6) .
C5 H5A 0.9500 .
C6 C7 1.404(6) .
C6 H6A 0.9500 .
C7 C8 1.451(6) .
C9 C10 1.462(6) .
C10 C11 1.384(6) .
C10 C15 1.420(6) .
C11 C12 1.383(7) .
C11 H11A 0.9500 .
C12 C13 1.396(8) .
C12 H12A 0.9500 .
C13 C14 1.382(7) .
C13 H13A 0.9500 .
C14 C15 1.397(6) .
C14 H14A 0.9500 .
C15 C16 1.466(6) .
C17 C18 1.452(6) .
C18 C19 1.392(6) .
C18 C23 1.432(6) .
C19 C20 1.386(7) .
C19 H19A 0.9500 .
C20 C21 1.393(7) .
C20 H20A 0.9500 .
C21 C22 1.391(7) .
C21 H21A 0.9500 .
C22 C23 1.391(6) .
C22 H22A 0.9500 .
C23 C24 1.440(6) .
C25 C30 1.398(6) .
C25 C26 1.403(6) .
C26 C27 1.395(6) .
C27 C28 1.380(7) .
C27 H27A 0.9500 .
C28 C29 1.373(7) .
C28 H28A 0.9500 .
C29 C30 1.392(7) .
C29 H29A 0.9500 .
C30 H30A 0.9500 .
C1S C2S 1.380(7) .
C1S C3S 1.388(7) 3_656
C1S H1S 0.9500 .
C2S C3S 1.384(7) .
C2S H2S 0.9500 .
C3S C1S 1.388(7) 3_656
C3S H3S 0.9500 .
