#------------------------------------------------------------------------------
#$Date: 2016-03-24 03:15:55 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179621 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/85/4508531.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_4508531
loop_
_publ_author_name
'Paton, Andrew S.'
'Morse, Graham E.'
'Lough, Alan J.'
'Bender, Timothy P.'
_publ_section_title
;
 Utilizing the π-Acidity of Boron Subphthalocyanine To Achieve Novel
 Solid-State Arrangements
;
_journal_issue                   12
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              5368
_journal_paper_doi               10.1021/cg4012795
_journal_volume                  13
_journal_year                    2013
_chemical_formula_moiety         'C34 H7 B F12 N6 O, 0.5(C6 H6)'
_chemical_formula_sum            'C37 H10 B F12 N6 O'
_chemical_formula_weight         793.32
_chemical_name_common            ' β-naphthoxy-dodecafluorosubphthalocyanine'
_chemical_name_systematic
' (2-naphthoxy)(dodecafluorosubphthalocyaninato)boron'
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.5833(4)
_cell_length_b                   12.7133(3)
_cell_length_c                   41.9519(16)
_cell_measurement_reflns_used    16359
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      2.6
_cell_volume                     6177.9(3)
_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 0.991
_diffrn_measured_fraction_theta_max 0.991
_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  0.1246
_diffrn_reflns_av_sigmaI/netI    0.0910
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       49
_diffrn_reflns_limit_l_min       -49
_diffrn_reflns_number            23743
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.57
_exptl_absorpt_coefficient_mu    0.156
_exptl_absorpt_correction_T_max  1.102
_exptl_absorpt_correction_T_min  0.382
_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    1.706
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             3160
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.400
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     514
_refine_ls_number_reflns         5392
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.1439
_refine_ls_R_factor_gt           0.0646
_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)+(0.1044P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1520
_refine_ls_wR_factor_ref         0.2045
_reflns_number_gt                2749
_reflns_number_total             5392
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cg4012795_si_006.cif
_cod_data_source_block           k1113
_cod_database_code               4508531
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -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
F1 F 0.2692(2) 0.44124(17) 0.07376(6) 0.0472(7) Uani 1 1 d .
F2 F 0.07851(19) 0.45434(17) 0.11041(7) 0.0516(7) Uani 1 1 d .
F3 F 0.0927(2) 0.44883(18) 0.17433(7) 0.0571(8) Uani 1 1 d .
F4 F 0.2992(2) 0.43206(19) 0.20407(7) 0.0547(7) Uani 1 1 d .
F5 F 0.6364(3) 0.5564(2) 0.25395(6) 0.0667(8) Uani 1 1 d .
F6 F 0.7868(3) 0.6998(2) 0.27760(7) 0.0805(10) Uani 1 1 d .
F7 F 0.9743(2) 0.7584(2) 0.24455(7) 0.0721(9) Uani 1 1 d .
F8 F 1.0135(2) 0.68505(18) 0.18486(6) 0.0541(7) Uani 1 1 d .
F9 F 0.9811(2) 0.70275(18) 0.07291(6) 0.0509(7) Uani 1 1 d .
F10 F 0.9170(2) 0.78387(19) 0.01560(7) 0.0632(8) Uani 1 1 d .
F11 F 0.7256(2) 0.7185(2) -0.01392(6) 0.0614(8) Uani 1 1 d .
F12 F 0.5863(2) 0.57079(18) 0.01260(6) 0.0546(7) Uani 1 1 d .
O1 O 0.7311(2) 0.2923(2) 0.12910(7) 0.0436(8) Uani 1 1 d .
N1 N 0.5719(3) 0.4111(2) 0.13339(8) 0.0358(9) Uani 1 1 d .
N2 N 0.5690(3) 0.4478(3) 0.18920(9) 0.0437(10) Uani 1 1 d .
N3 N 0.7435(3) 0.4630(2) 0.15902(8) 0.0370(9) Uani 1 1 d .
N4 N 0.8783(3) 0.5658(2) 0.12964(9) 0.0357(9) Uani 1 1 d .
N5 N 0.7302(3) 0.4699(2) 0.10292(8) 0.0328(8) Uani 1 1 d .
N6 N 0.5438(3) 0.4576(2) 0.07909(8) 0.0358(9) Uani 1 1 d .
C1 C 0.5026(3) 0.4264(3) 0.10767(10) 0.0357(10) Uani 1 1 d .
C2 C 0.3859(4) 0.4271(3) 0.12004(11) 0.0366(11) Uani 1 1 d .
C3 C 0.2790(4) 0.4364(3) 0.10548(11) 0.0385(11) Uani 1 1 d .
C4 C 0.1814(4) 0.4431(3) 0.12421(12) 0.0396(11) Uani 1 1 d .
C5 C 0.1892(4) 0.4406(3) 0.15707(12) 0.0408(11) Uani 1 1 d .
C6 C 0.2947(4) 0.4321(3) 0.17189(12) 0.0431(12) Uani 1 1 d .
C7 C 0.3939(4) 0.4237(3) 0.15369(11) 0.0384(11) Uani 1 1 d .
C8 C 0.5152(4) 0.4218(3) 0.16185(11) 0.0379(11) Uani 1 1 d .
C9 C 0.6812(4) 0.4745(3) 0.18640(11) 0.0403(11) Uani 1 1 d .
C10 C 0.7494(4) 0.5425(3) 0.20677(11) 0.0412(11) Uani 1 1 d .
C11 C 0.7287(4) 0.5845(4) 0.23701(12) 0.0516(13) Uani 1 1 d .
C12 C 0.8042(5) 0.6583(4) 0.24889(12) 0.0597(14) Uani 1 1 d .
C13 C 0.9006(4) 0.6901(4) 0.23129(12) 0.0522(13) Uani 1 1 d .
C14 C 0.9208(4) 0.6507(3) 0.20121(11) 0.0452(12) Uani 1 1 d .
C15 C 0.8457(4) 0.5780(3) 0.18844(10) 0.0363(11) Uani 1 1 d .
C16 C 0.8349(4) 0.5322(3) 0.15734(11) 0.0359(10) Uani 1 1 d .
C17 C 0.8202(3) 0.5401(3) 0.10309(11) 0.0351(10) Uani 1 1 d .
C18 C 0.8155(3) 0.5924(3) 0.07233(10) 0.0355(10) Uani 1 1 d .
C19 C 0.8841(4) 0.6688(3) 0.05895(11) 0.0429(11) Uani 1 1 d .
C20 C 0.8512(4) 0.7114(3) 0.02989(12) 0.0484(12) Uani 1 1 d .
C21 C 0.7522(4) 0.6772(3) 0.01461(11) 0.0458(12) Uani 1 1 d .
C22 C 0.6817(4) 0.6022(3) 0.02814(11) 0.0434(12) Uani 1 1 d .
C23 C 0.7136(4) 0.5578(3) 0.05700(10) 0.0356(10) Uani 1 1 d .
C24 C 0.6554(4) 0.4857(3) 0.07816(10) 0.0373(11) Uani 1 1 d .
C25 C 0.8445(4) 0.2622(3) 0.13178(11) 0.0378(11) Uani 1 1 d .
C26 C 0.8899(4) 0.2429(3) 0.16208(12) 0.0444(12) Uani 1 1 d .
H26A H 0.8415 0.2499 0.1802 0.053 Uiso 1 1 calc R
C27 C 1.0027(4) 0.2142(3) 0.16603(11) 0.0439(12) Uani 1 1 d .
H27A H 1.0316 0.2016 0.1869 0.053 Uiso 1 1 calc R
C28 C 1.0770(4) 0.2032(3) 0.13947(11) 0.0391(11) Uani 1 1 d .
C29 C 1.1980(4) 0.1842(3) 0.14289(12) 0.0427(12) Uani 1 1 d .
H29A H 1.2299 0.1739 0.1635 0.051 Uiso 1 1 calc R
C30 C 1.2679(4) 0.1806(3) 0.11690(12) 0.0446(12) Uani 1 1 d .
H30A H 1.3488 0.1713 0.1194 0.053 Uiso 1 1 calc R
C31 C 1.2195(4) 0.1908(3) 0.08625(12) 0.0465(12) Uani 1 1 d .
H31A H 1.2679 0.1849 0.0680 0.056 Uiso 1 1 calc R
C32 C 1.1053(4) 0.2087(3) 0.08231(12) 0.0501(13) Uani 1 1 d .
H32A H 1.0751 0.2146 0.0613 0.060 Uiso 1 1 calc R
C33 C 1.0304(4) 0.2189(3) 0.10830(11) 0.0391(11) Uani 1 1 d .
C34 C 0.9120(4) 0.2477(3) 0.10507(12) 0.0429(12) Uani 1 1 d .
H34A H 0.8795 0.2569 0.0845 0.051 Uiso 1 1 calc R
B1 B 0.6997(4) 0.4017(4) 0.13099(12) 0.0378(13) Uani 1 1 d .
C1S C 0.0356(4) 0.4561(4) 0.02866(12) 0.0543(13) Uani 1 1 d .
H1S H 0.0598 0.4256 0.0482 0.065 Uiso 1 1 calc R
C2S C -0.0668(4) 0.4245(3) 0.01446(13) 0.0530(13) Uani 1 1 d .
H2S H -0.1132 0.3725 0.0245 0.064 Uiso 1 1 calc R
C3S C -0.1020(4) 0.4678(4) -0.01403(12) 0.0532(13) Uani 1 1 d .
H3S H -0.1720 0.4452 -0.0236 0.064 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'
F F 0.0171 0.0103 '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 120.5(3) . .
C1 N1 C8 113.3(4) . .
C1 N1 B1 123.0(4) . .
C8 N1 B1 123.0(4) . .
C8 N2 C9 115.7(4) . .
C9 N3 C16 112.4(4) . .
C9 N3 B1 122.4(4) . .
C16 N3 B1 123.5(4) . .
C16 N4 C17 117.1(4) . .
C24 N5 C17 112.9(3) . .
C24 N5 B1 122.0(4) . .
C17 N5 B1 123.3(4) . .
C24 N6 C1 116.4(4) . .
N6 C1 N1 122.6(4) . .
N6 C1 C2 130.3(4) . .
N1 C1 C2 105.5(4) . .
C3 C2 C7 120.0(4) . .
C3 C2 C1 132.6(4) . .
C7 C2 C1 107.3(4) . .
F1 C3 C4 119.6(4) . .
F1 C3 C2 121.3(4) . .
C4 C3 C2 119.1(4) . .
F2 C4 C3 119.5(4) . .
F2 C4 C5 119.6(4) . .
C3 C4 C5 120.8(4) . .
F3 C5 C6 120.3(5) . .
F3 C5 C4 118.9(4) . .
C6 C5 C4 120.8(4) . .
F4 C6 C5 119.1(4) . .
F4 C6 C7 121.3(4) . .
C5 C6 C7 119.6(5) . .
C6 C7 C2 119.6(4) . .
C6 C7 C8 132.6(5) . .
C2 C7 C8 107.4(4) . .
N2 C8 N1 123.0(4) . .
N2 C8 C7 130.3(4) . .
N1 C8 C7 105.1(4) . .
N2 C9 N3 123.8(4) . .
N2 C9 C10 128.6(4) . .
N3 C9 C10 105.7(4) . .
C11 C10 C15 120.1(4) . .
C11 C10 C9 132.1(4) . .
C15 C10 C9 107.3(4) . .
F5 C11 C12 120.0(5) . .
F5 C11 C10 121.2(5) . .
C12 C11 C10 118.8(5) . .
F6 C12 C11 120.2(5) . .
F6 C12 C13 119.0(5) . .
C11 C12 C13 120.9(5) . .
F7 C13 C14 120.5(5) . .
F7 C13 C12 118.5(5) . .
C14 C13 C12 120.9(4) . .
F8 C14 C15 121.5(4) . .
F8 C14 C13 119.0(4) . .
C15 C14 C13 119.5(4) . .
C14 C15 C10 119.7(4) . .
C14 C15 C16 133.0(4) . .
C10 C15 C16 107.0(4) . .
N4 C16 N3 122.6(4) . .
N4 C16 C15 128.9(4) . .
N3 C16 C15 106.2(4) . .
N4 C17 N5 122.9(4) . .
N4 C17 C18 130.2(4) . .
N5 C17 C18 105.3(4) . .
C19 C18 C23 121.1(4) . .
C19 C18 C17 131.6(4) . .
C23 C18 C17 107.1(3) . .
F9 C19 C18 122.3(4) . .
F9 C19 C20 119.3(4) . .
C18 C19 C20 118.4(4) . .
F10 C20 C21 118.7(4) . .
F10 C20 C19 120.4(5) . .
C21 C20 C19 120.8(4) . .
F11 C21 C22 120.1(4) . .
F11 C21 C20 118.7(4) . .
C22 C21 C20 121.2(4) . .
F12 C22 C21 119.6(4) . .
F12 C22 C23 121.5(4) . .
C21 C22 C23 118.9(4) . .
C22 C23 C18 119.5(4) . .
C22 C23 C24 132.2(4) . .
C18 C23 C24 107.9(4) . .
N6 C24 N5 123.3(4) . .
N6 C24 C23 129.6(4) . .
N5 C24 C23 105.3(4) . .
O1 C25 C34 120.9(4) . .
O1 C25 C26 118.9(4) . .
C34 C25 C26 120.2(4) . .
C27 C26 C25 121.1(4) . .
C27 C26 H26A 119.4 . .
C25 C26 H26A 119.4 . .
C26 C27 C28 120.8(4) . .
C26 C27 H27A 119.6 . .
C28 C27 H27A 119.6 . .
C27 C28 C33 118.5(4) . .
C27 C28 C29 122.3(4) . .
C33 C28 C29 119.1(4) . .
C30 C29 C28 120.6(4) . .
C30 C29 H29A 119.7 . .
C28 C29 H29A 119.7 . .
C29 C30 C31 119.5(4) . .
C29 C30 H30A 120.3 . .
C31 C30 H30A 120.3 . .
C32 C31 C30 121.1(4) . .
C32 C31 H31A 119.5 . .
C30 C31 H31A 119.5 . .
C31 C32 C33 121.8(5) . .
C31 C32 H32A 119.1 . .
C33 C32 H32A 119.1 . .
C32 C33 C34 123.1(4) . .
C32 C33 C28 117.8(4) . .
C34 C33 C28 119.1(4) . .
C25 C34 C33 120.2(4) . .
C25 C34 H34A 119.9 . .
C33 C34 H34A 119.9 . .
O1 B1 N1 109.4(4) . .
O1 B1 N3 117.4(4) . .
N1 B1 N3 104.0(4) . .
O1 B1 N5 117.0(4) . .
N1 B1 N5 103.9(3) . .
N3 B1 N5 103.6(4) . .
C3S C1S C2S 119.2(5) 5_565 .
C3S C1S H1S 120.4 5_565 .
C2S C1S H1S 120.4 . .
C3S C2S C1S 120.7(5) . .
C3S C2S H2S 119.6 . .
C1S C2S H2S 119.6 . .
C2S C3S C1S 120.1(5) . 5_565
C2S C3S H3S 120.0 . .
C1S C3S H3S 120.0 5_565 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C3 1.337(5) .
F2 C4 1.333(5) .
F3 C5 1.336(5) .
F4 C6 1.351(5) .
F5 C11 1.333(5) .
F6 C12 1.330(5) .
F7 C13 1.339(5) .
F8 C14 1.346(5) .
F9 C19 1.338(5) .
F10 C20 1.338(5) .
F11 C21 1.343(5) .
F12 C22 1.343(5) .
O1 C25 1.373(5) .
O1 B1 1.439(6) .
N1 C1 1.359(5) .
N1 C8 1.369(5) .
N1 B1 1.489(6) .
N2 C8 1.347(5) .
N2 C9 1.348(5) .
N3 C9 1.365(5) .
N3 C16 1.377(5) .
N3 B1 1.500(6) .
N4 C16 1.337(5) .
N4 C17 1.341(5) .
N5 C24 1.368(5) .
N5 C17 1.373(5) .
N5 B1 1.505(6) .
N6 C24 1.342(5) .
N6 C1 1.350(5) .
C1 C2 1.448(6) .
C2 C3 1.386(6) .
C2 C7 1.415(6) .
C3 C4 1.380(6) .
C4 C5 1.382(6) .
C5 C6 1.375(6) .
C6 C7 1.384(6) .
C7 C8 1.447(6) .
C9 C10 1.449(6) .
C10 C11 1.397(6) .
C10 C15 1.429(6) .
C11 C12 1.376(7) .
C12 C13 1.398(7) .
C13 C14 1.378(6) .
C14 C15 1.378(6) .
C15 C16 1.435(6) .
C17 C18 1.453(6) .
C18 C19 1.375(6) .
C18 C23 1.414(6) .
C19 C20 1.387(6) .
C20 C21 1.383(6) .
C21 C22 1.378(6) .
C22 C23 1.386(6) .
C23 C24 1.443(6) .
C25 C34 1.379(6) .
C25 C26 1.397(6) .
C26 C27 1.367(6) .
C26 H26A 0.9500 .
C27 C28 1.415(6) .
C27 H27A 0.9500 .
C28 C33 1.429(6) .
C28 C29 1.429(6) .
C29 C30 1.359(6) .
C29 H29A 0.9500 .
C30 C31 1.409(6) .
C30 H30A 0.9500 .
C31 C32 1.352(6) .
C31 H31A 0.9500 .
C32 C33 1.399(6) .
C32 H32A 0.9500 .
C33 C34 1.427(6) .
C34 H34A 0.9500 .
C1S C3S 1.381(6) 5_565
C1S C2S 1.386(6) .
C1S H1S 0.9500 .
C2S C3S 1.377(7) .
C2S H2S 0.9500 .
C3S C1S 1.381(6) 5_565
C3S H3S 0.9500 .
