#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/93/2229302.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2229302
loop_
_publ_author_name
'Paton, Andrew S.'
'Lough, Alan J.'
'Bender, Timothy P.'
_publ_section_title
;
 (4-Cyanophenolato)(subphthalocyaninato)boron
;
_journal_coeditor_code           ZL2323
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o505
_journal_page_last               o506
_journal_paper_doi               10.1107/S1600536811000869
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C31 H16 B N7 O'
_chemical_formula_moiety         'C31 H16 B N7 O'
_chemical_formula_sum            'C31 H16 B N7 O'
_chemical_formula_weight         513.32
_chemical_name_systematic
;
(4-cyanophenolato)(1,2,3,4,8,9,10,11,15,16,17,18-dodecafluoro-7,12:14,19-
diimino-21,5-nitrilo-5H-
tribenzo[c,h,m][1,6,11]triazacyclopentadecinato)boron
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 119.4050(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   16.2310(3)
_cell_length_b                   27.5129(7)
_cell_length_c                   13.4385(2)
_cell_measurement_reflns_used    21404
_cell_measurement_temperature    150.0(10)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.6
_cell_volume                     5228.00(19)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2002)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
'PLATON (Spek, 2009) and Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150.0(10)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_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  0.087
_diffrn_reflns_av_sigmaI/netI    0.045
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            21404
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         2.65
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.711
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SORTAV; Blessing, 1995)
;
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2112
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.263
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         5914
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0719
_refine_ls_R_factor_gt           0.0486
_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)+(0.0863P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1294
_refine_ls_wR_factor_ref         0.1412
_reflns_number_gt                4290
_reflns_number_total             5914
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            zl2323.cif
_cod_data_source_block           I
_cod_original_cell_volume        5228.00(18)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2229302
_cod_database_fobs_code          2229302
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.45381(6) 0.13599(4) 0.37150(8) 0.0282(3) Uani d . 1 . .
N N1 0.29842(7) 0.16745(5) 0.25275(9) 0.0239(3) Uani d . 1 . .
N N2 0.20587(8) 0.09502(5) 0.20043(10) 0.0279(3) Uani d . 1 . .
N N3 0.31564(8) 0.11128(5) 0.39600(10) 0.0250(3) Uani d . 1 . .
N N4 0.34779(8) 0.14317(5) 0.57623(10) 0.0269(3) Uani d . 1 . .
N N5 0.37213(7) 0.19169(5) 0.44565(9) 0.0234(3) Uani d . 1 . .
N N6 0.32295(8) 0.25170(5) 0.30000(10) 0.0256(3) Uani d . 1 . .
N N7 0.89695(9) 0.09629(6) 0.79845(12) 0.0423(4) Uani d . 1 . .
C C1 0.28553(9) 0.21531(6) 0.22298(12) 0.0244(3) Uani d . 1 . .
C C2 0.20815(9) 0.21704(6) 0.10579(11) 0.0246(3) Uani d . 1 . .
C C3 0.16247(10) 0.25605(6) 0.03201(12) 0.0276(3) Uani d . 1 . .
H H3A 0.1862 0.2883 0.0515 0.033 Uiso calc R 1 . .
C C4 0.08163(11) 0.24607(6) -0.07024(12) 0.0319(4) Uani d . 1 . .
H H4A 0.0503 0.2718 -0.1225 0.038 Uiso calc R 1 . .
C C5 0.04511(10) 0.19906(6) -0.09831(12) 0.0324(4) Uani d . 1 . .
H H5A -0.0114 0.1937 -0.1685 0.039 Uiso calc R 1 . .
C C6 0.08894(10) 0.16012(6) -0.02685(12) 0.0285(3) Uani d . 1 . .
H H6A 0.0637 0.1282 -0.0467 0.034 Uiso calc R 1 . .
C C7 0.17179(9) 0.16932(6) 0.07568(11) 0.0249(3) Uani d . 1 . .
C C8 0.22770(9) 0.13839(6) 0.17416(11) 0.0245(3) Uani d . 1 . .
C C9 0.24642(10) 0.08345(6) 0.31192(12) 0.0266(3) Uani d . 1 . .
C C10 0.21193(10) 0.05125(6) 0.36928(12) 0.0295(3) Uani d . 1 . .
C C11 0.14170(11) 0.01560(6) 0.32724(14) 0.0343(4) Uani d . 1 . .
H H11A 0.1111 0.0063 0.2491 0.041 Uiso calc R 1 . .
C C12 0.11801(12) -0.00584(6) 0.40292(15) 0.0401(4) Uani d . 1 . .
H H12A 0.0717 -0.0308 0.3765 0.048 Uiso calc R 1 . .
C C13 0.16061(13) 0.00841(7) 0.51697(15) 0.0411(4) Uani d . 1 . .
H H13A 0.1427 -0.0070 0.5667 0.049 Uiso calc R 1 . .
C C14 0.22856(12) 0.04466(6) 0.55934(14) 0.0371(4) Uani d . 1 . .
H H14A 0.2566 0.0546 0.6369 0.044 Uiso calc R 1 . .
C C15 0.25479(10) 0.06624(6) 0.48518(12) 0.0294(4) Uani d . 1 . .
C C16 0.31566(10) 0.10753(6) 0.49800(12) 0.0272(3) Uani d . 1 . .
C C17 0.36934(9) 0.18587(6) 0.54540(11) 0.0250(3) Uani d . 1 . .
C C18 0.37682(9) 0.23457(6) 0.59076(11) 0.0256(3) Uani d . 1 . .
C C19 0.38193(9) 0.25146(6) 0.69168(12) 0.0290(4) Uani d . 1 . .
H H19A 0.3810 0.2296 0.7459 0.035 Uiso calc R 1 . .
C C20 0.38842(10) 0.30100(6) 0.70979(13) 0.0320(4) Uani d . 1 . .
H H20A 0.3938 0.3133 0.7788 0.038 Uiso calc R 1 . .
C C21 0.38732(10) 0.33359(6) 0.62963(13) 0.0333(4) Uani d . 1 . .
H H21A 0.3933 0.3674 0.6459 0.040 Uiso calc R 1 . .
C C22 0.37760(9) 0.31749(6) 0.52658(13) 0.0309(4) Uani d . 1 . .
H H22A 0.3741 0.3398 0.4707 0.037 Uiso calc R 1 . .
C C23 0.37317(9) 0.26767(6) 0.50768(11) 0.0257(3) Uani d . 1 . .
C C24 0.36076(9) 0.23903(6) 0.41071(12) 0.0244(3) Uani d . 1 . .
C C25 0.54079(9) 0.12725(6) 0.46227(12) 0.0252(3) Uani d . 1 . .
C C26 0.61048(10) 0.11309(6) 0.43571(12) 0.0280(3) Uani d . 1 . .
H H26A 0.5952 0.1096 0.3582 0.034 Uiso calc R 1 . .
C C27 0.70191(10) 0.10419(6) 0.52242(12) 0.0286(3) Uani d . 1 . .
H H27A 0.7487 0.0937 0.5042 0.034 Uiso calc R 1 . .
C C28 0.72545(10) 0.11047(6) 0.63614(12) 0.0275(3) Uani d . 1 . .
C C29 0.65582(11) 0.12432(6) 0.66259(13) 0.0316(4) Uani d . 1 . .
H H29A 0.6715 0.1285 0.7401 0.038 Uiso calc R 1 . .
C C30 0.56400(10) 0.13197(6) 0.57646(12) 0.0306(4) Uani d . 1 . .
H H30A 0.5165 0.1405 0.5951 0.037 Uiso calc R 1 . .
C C31 0.82104(11) 0.10284(6) 0.72633(13) 0.0308(4) Uani d . 1 . .
B B1 0.36726(11) 0.15027(7) 0.37081(13) 0.0256(4) Uani d . 1 . .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C25 O1 B1 . . 128.89(11) ?
C1 N1 C8 . . 112.80(11) ?
C1 N1 B1 . . 122.86(12) ?
C8 N1 B1 . . 122.55(13) ?
C8 N2 C9 . . 117.12(12) ?
C9 N3 C16 . . 112.27(12) ?
C9 N3 B1 . . 122.45(12) ?
C16 N3 B1 . . 123.54(12) ?
C16 N4 C17 . . 117.12(13) ?
C24 N5 C17 . . 112.54(12) ?
C24 N5 B1 . . 122.79(12) ?
C17 N5 B1 . . 123.46(13) ?
C24 N6 C1 . . 116.35(13) ?
N6 C1 N1 . . 123.02(12) ?
N6 C1 C2 . . 129.00(14) ?
N1 C1 C2 . . 106.01(12) ?
C3 C2 C7 . . 120.47(13) ?
C3 C2 C1 . . 131.80(14) ?
C7 C2 C1 . . 107.24(13) ?
C4 C3 C2 . . 117.71(15) ?
C4 C3 H3A . . 121.1 ?
C2 C3 H3A . . 121.1 ?
C3 C4 C5 . . 121.48(15) ?
C3 C4 H4A . . 119.3 ?
C5 C4 H4A . . 119.3 ?
C6 C5 C4 . . 121.73(14) ?
C6 C5 H5A . . 119.1 ?
C4 C5 H5A . . 119.1 ?
C5 C6 C7 . . 117.60(15) ?
C5 C6 H6A . . 121.2 ?
C7 C6 H6A . . 121.2 ?
C6 C7 C2 . . 120.97(13) ?
C6 C7 C8 . . 131.24(15) ?
C2 C7 C8 . . 107.23(12) ?
N2 C8 N1 . . 123.06(13) ?
N2 C8 C7 . . 129.22(13) ?
N1 C8 C7 . . 105.76(13) ?
N2 C9 N3 . . 122.72(14) ?
N2 C9 C10 . . 128.97(13) ?
N3 C9 C10 . . 106.04(12) ?
C11 C10 C15 . . 120.73(14) ?
C11 C10 C9 . . 131.58(14) ?
C15 C10 C9 . . 107.20(13) ?
C12 C11 C10 . . 117.94(15) ?
C12 C11 H11A . . 121.0 ?
C10 C11 H11A . . 121.0 ?
C11 C12 C13 . . 121.46(16) ?
C11 C12 H12A . . 119.3 ?
C13 C12 H12A . . 119.3 ?
C14 C13 C12 . . 121.33(16) ?
C14 C13 H13A . . 119.3 ?
C12 C13 H13A . . 119.3 ?
C13 C14 C15 . . 118.27(15) ?
C13 C14 H14A . . 120.9 ?
C15 C14 H14A . . 120.9 ?
C14 C15 C10 . . 120.23(14) ?
C14 C15 C16 . . 132.36(15) ?
C10 C15 C16 . . 107.11(13) ?
N4 C16 N3 . . 122.43(14) ?
N4 C16 C15 . . 129.92(14) ?
N3 C16 C15 . . 105.78(13) ?
N4 C17 N5 . . 122.68(13) ?
N4 C17 C18 . . 130.99(13) ?
N5 C17 C18 . . 105.44(13) ?
C19 C18 C23 . . 120.65(15) ?
C19 C18 C17 . . 131.87(15) ?
C23 C18 C17 . . 107.41(12) ?
C20 C19 C18 . . 117.58(15) ?
C20 C19 H19A . . 121.2 ?
C18 C19 H19A . . 121.2 ?
C19 C20 C21 . . 121.86(14) ?
C19 C20 H20A . . 119.1 ?
C21 C20 H20A . . 119.1 ?
C22 C21 C20 . . 121.19(16) ?
C22 C21 H21A . . 119.4 ?
C20 C21 H21A . . 119.4 ?
C21 C22 C23 . . 117.89(15) ?
C21 C22 H22A . . 121.1 ?
C23 C22 H22A . . 121.1 ?
C22 C23 C18 . . 120.72(13) ?
C22 C23 C24 . . 132.25(14) ?
C18 C23 C24 . . 106.98(14) ?
N6 C24 N5 . . 122.53(13) ?
N6 C24 C23 . . 129.70(14) ?
N5 C24 C23 . . 105.88(12) ?
O1 C25 C30 . . 124.84(13) ?
O1 C25 C26 . . 115.73(12) ?
C30 C25 C26 . . 119.42(13) ?
C27 C26 C25 . . 120.06(13) ?
C27 C26 H26A . . 120.0 ?
C25 C26 H26A . . 120.0 ?
C26 C27 C28 . . 120.29(14) ?
C26 C27 H27A . . 119.9 ?
C28 C27 H27A . . 119.9 ?
C27 C28 C29 . . 119.60(13) ?
C27 C28 C31 . . 120.48(13) ?
C29 C28 C31 . . 119.91(14) ?
C30 C29 C28 . . 120.25(14) ?
C30 C29 H29A . . 119.9 ?
C28 C29 H29A . . 119.9 ?
C29 C30 C25 . . 120.32(14) ?
C29 C30 H30A . . 119.8 ?
C25 C30 H30A . . 119.8 ?
N7 C31 C28 . . 179.29(19) ?
O1 B1 N5 . . 117.99(12) ?
O1 B1 N3 . . 116.79(13) ?
N5 B1 N3 . . 104.14(12) ?
O1 B1 N1 . . 107.91(12) ?
N5 B1 N1 . . 103.72(12) ?
N3 B1 N1 . . 104.83(12) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C25 . 1.3593(16) ?
O1 B1 . 1.4544(18) ?
N1 C1 . 1.362(2) ?
N1 C8 . 1.3718(18) ?
N1 B1 . 1.4995(19) ?
N2 C8 . 1.340(2) ?
N2 C9 . 1.3458(18) ?
N3 C9 . 1.3706(18) ?
N3 C16 . 1.3744(18) ?
N3 B1 . 1.499(2) ?
N4 C16 . 1.342(2) ?
N4 C17 . 1.348(2) ?
N5 C24 . 1.3658(19) ?
N5 C17 . 1.3726(18) ?
N5 B1 . 1.496(2) ?
N6 C24 . 1.3473(18) ?
N6 C1 . 1.3510(19) ?
N7 C31 . 1.1476(19) ?
C1 C2 . 1.4553(18) ?
C2 C3 . 1.401(2) ?
C2 C7 . 1.415(2) ?
C3 C4 . 1.384(2) ?
C3 H3A . 0.9500 ?
C4 C5 . 1.395(2) ?
C4 H4A . 0.9500 ?
C5 C6 . 1.380(2) ?
C5 H5A . 0.9500 ?
C6 C7 . 1.3969(19) ?
C6 H6A . 0.9500 ?
C7 C8 . 1.456(2) ?
C9 C10 . 1.455(2) ?
C10 C11 . 1.396(2) ?
C10 C15 . 1.420(2) ?
C11 C12 . 1.384(2) ?
C11 H11A . 0.9500 ?
C12 C13 . 1.393(2) ?
C12 H12A . 0.9500 ?
C13 C14 . 1.385(2) ?
C13 H13A . 0.9500 ?
C14 C15 . 1.394(2) ?
C14 H14A . 0.9500 ?
C15 C16 . 1.459(2) ?
C17 C18 . 1.452(2) ?
C18 C19 . 1.397(2) ?
C18 C23 . 1.419(2) ?
C19 C20 . 1.379(2) ?
C19 H19A . 0.9500 ?
C20 C21 . 1.395(2) ?
C20 H20A . 0.9500 ?
C21 C22 . 1.387(2) ?
C21 H21A . 0.9500 ?
C22 C23 . 1.389(2) ?
C22 H22A . 0.9500 ?
C23 C24 . 1.450(2) ?
C25 C30 . 1.395(2) ?
C25 C26 . 1.398(2) ?
C26 C27 . 1.386(2) ?
C26 H26A . 0.9500 ?
C27 C28 . 1.392(2) ?
C27 H27A . 0.9500 ?
C28 C29 . 1.394(2) ?
C28 C31 . 1.440(2) ?
C29 C30 . 1.382(2) ?
C29 H29A . 0.9500 ?
C30 H30A . 0.9500 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C3 H3A Cg1 8_455 0.95 2.70 3.499(3) 143
C20 H20A Cg2 7_556 0.95 2.59 3.254(4) 127
C21 H21A Cg3 7_556 0.95 2.70 3.238(4) 116
