#------------------------------------------------------------------------------
#$Date: 2016-03-24 03:15:55 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179621 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/85/4508527.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_4508527
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 H19 B N6 O'
_chemical_formula_sum            'C34 H19 B N6 O'
_chemical_formula_weight         538.36
_chemical_name_common            ' α-naphthoxy-boronsubphthalocyanine'
_chemical_name_systematic        ' (1-naphthoxy)(subphthalocyaninato)boron'
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2013-01-24 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.4536(2)
_cell_length_b                   14.0050(4)
_cell_length_c                   10.2555(5)
_cell_measurement_reflns_used    14182
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.7
_cell_volume                     2506.83(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 0.995
_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  0.0581
_diffrn_reflns_av_sigmaI/netI    0.0460
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14182
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.72
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.740
_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    1.426
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       0.0108(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.155
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2979
_refine_ls_number_restraints     25
_refine_ls_restrained_S_all      1.150
_refine_ls_R_factor_all          0.1298
_refine_ls_R_factor_gt           0.0957
_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)+(0.0000P)²+8.7215P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2025
_refine_ls_wR_factor_ref         0.2156
_reflns_number_gt                2097
_reflns_number_total             2979
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cg4012795_si_002.cif
_cod_data_source_block           k09263a
_cod_database_code               4508527
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'
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
O1 O 0.9383(2) 0.2500 0.0575(4) 0.0399(10) Uani 1 2 d S . .
N1 N 0.9369(2) 0.2500 0.3015(4) 0.0375(11) Uani 1 2 d S . .
N2 N 0.91571(17) 0.4148(3) 0.3495(3) 0.0398(8) Uani 1 1 d . . .
N3 N 0.84035(18) 0.3335(3) 0.1889(3) 0.0424(9) Uani 1 1 d . . .
N4 N 0.7283(3) 0.2500 0.1213(5) 0.0484(14) Uani 1 2 d S . .
C1 C 1.0550(2) 0.2995(3) 0.6946(4) 0.0391(9) Uani 1 1 d . . .
H1 H 1.0759 0.3326 0.7672 0.047 Uiso 1 1 calc R . .
C2 C 1.0252(2) 0.3515(3) 0.5913(4) 0.0362(9) Uani 1 1 d . A .
H2 H 1.0259 0.4193 0.5915 0.043 Uiso 1 1 calc R . .
C3 C 0.9940(2) 0.3006(3) 0.4867(3) 0.0342(9) Uani 1 1 d . . .
C4 C 0.9519(2) 0.3315(3) 0.3714(4) 0.0368(9) Uani 1 1 d . A .
C5 C 0.8566(2) 0.4123(3) 0.2641(4) 0.0405(10) Uani 1 1 d . A .
C6 C 0.7905(2) 0.4748(3) 0.2554(4) 0.0441(11) Uani 1 1 d . . .
C7 C 0.7743(2) 0.5624(3) 0.3121(4) 0.0487(11) Uani 1 1 d . A .
H7 H 0.8115 0.5943 0.3637 0.058 Uiso 1 1 calc R . .
C8 C 0.7027(3) 0.6020(3) 0.2916(5) 0.0583(13) Uani 1 1 d . . .
H8 H 0.6909 0.6627 0.3277 0.070 Uiso 1 1 calc R A .
C9 C 0.6476(3) 0.5535(4) 0.2180(5) 0.0642(15) Uani 1 1 d . A .
H9 H 0.5989 0.5821 0.2053 0.077 Uiso 1 1 calc R . .
C10 C 0.6618(2) 0.4659(4) 0.1637(4) 0.0544(13) Uani 1 1 d . . .
H10 H 0.6235 0.4339 0.1145 0.065 Uiso 1 1 calc R A .
C11 C 0.7338(2) 0.4248(4) 0.1823(4) 0.0468(11) Uani 1 1 d . A .
C12 C 0.7648(2) 0.3317(4) 0.1507(4) 0.0444(11) Uani 1 1 d . A .
C13 C 1.00408(17) 0.3089(3) 0.0446(4) 0.0397(14) Uani 0.50 1 d PGU A -1
C14 C 0.9952(2) 0.4072(3) 0.0344(4) 0.0505(18) Uani 0.50 1 d PGU A -1
H14 H 0.9456 0.4348 0.0404 0.061 Uiso 0.50 1 calc PR A -1
C15 C 1.0589(3) 0.4652(2) 0.0153(5) 0.058(2) Uani 0.50 1 d PGU A -1
H15 H 1.0528 0.5324 0.0083 0.069 Uiso 0.50 1 calc PR A -1
C16 C 1.1314(3) 0.4248(3) 0.0064(5) 0.0516(18) Uani 0.50 1 d PGU A -1
H16 H 1.1749 0.4644 -0.0067 0.062 Uiso 0.50 1 calc PR A -1
C17 C 1.14031(18) 0.3264(3) 0.0166(3) 0.0416(15) Uani 0.50 1 d PGU A -1
C18 C 1.07664(18) 0.2685(2) 0.0357(2) 0.0378(14) Uani 0.50 1 d PGU A -1
C19 C 1.0855(3) 0.1701(2) 0.0459(4) 0.0471(17) Uani 0.50 1 d PGU A -1
H19 H 1.0420 0.1305 0.0590 0.057 Uiso 0.50 1 calc PR A -1
C20 C 1.1581(3) 0.1297(3) 0.0370(4) 0.057(2) Uani 0.50 1 d PGU A -1
H20 H 1.1641 0.0625 0.0440 0.069 Uiso 0.50 1 calc PR A -1
C21 C 1.2218(2) 0.1877(4) 0.0179(4) 0.069(3) Uani 0.50 1 d PGU A -1
H21 H 1.2713 0.1601 0.0119 0.083 Uiso 0.50 1 calc PR A -1
C22 C 1.21287(17) 0.2860(4) 0.0077(4) 0.058(2) Uani 0.50 1 d PGU A -1
H22 H 1.2564 0.3256 -0.0053 0.070 Uiso 0.50 1 calc PR A -1
B1 B 0.8929(4) 0.2500 0.1765(6) 0.0418(16) Uani 1 2 d S . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C13 O1 C13 71.0(3) . 8_565
C13 O1 B1 121.3(3) . .
C13 O1 B1 121.3(3) 8_565 .
C4 N1 C4 112.5(4) . 8_565
C4 N1 B1 123.1(2) . .
C4 N1 B1 123.1(2) 8_565 .
C4 N2 C5 116.3(4) . .
C12 N3 C5 111.9(4) . .
C12 N3 B1 123.3(4) . .
C5 N3 B1 123.4(3) . .
C12 N4 C12 116.7(5) . 8_565
C1 C1 C2 121.7(2) 8_565 .
C1 C2 C3 117.7(4) . .
C2 C3 C3 120.7(2) . 8_565
C2 C3 C4 131.8(4) . .
C3 C3 C4 107.2(2) 8_565 .
N2 C4 N1 123.0(3) . .
N2 C4 C3 129.0(4) . .
N1 C4 C3 105.8(4) . .
N2 C5 N3 122.7(4) . .
N2 C5 C6 129.1(4) . .
N3 C5 C6 106.6(3) . .
C7 C6 C11 121.0(4) . .
C7 C6 C5 132.0(4) . .
C11 C6 C5 106.7(4) . .
C8 C7 C6 118.4(4) . .
C7 C8 C9 120.5(5) . .
C10 C9 C8 122.1(5) . .
C9 C10 C11 118.5(5) . .
C10 C11 C6 119.6(5) . .
C10 C11 C12 132.6(4) . .
C6 C11 C12 107.5(4) . .
N4 C12 N3 122.3(4) . .
N4 C12 C11 129.8(4) . .
N3 C12 C11 106.1(4) . .
C14 C13 C18 120.0 . .
C14 C13 O1 119.5(2) . .
C18 C13 O1 120.4(2) . .
C13 C14 C15 120.0 . .
C16 C15 C14 120.0 . .
C15 C16 C17 120.0 . .
C16 C17 C18 120.0 . .
C16 C17 C22 120.0 . .
C18 C17 C22 120.0 . .
C19 C18 C17 120.0 . .
C19 C18 C13 120.0 . .
C17 C18 C13 120.0 . .
C18 C19 C20 120.0 . .
C19 C20 C21 120.0 . .
C22 C21 C20 120.0 . .
C21 C22 C17 120.0 . .
O1 B1 N3 114.0(3) . 8_565
O1 B1 N3 114.0(3) . .
N3 B1 N3 103.3(5) 8_565 .
O1 B1 N1 116.0(5) . .
N3 B1 N1 104.0(3) 8_565 .
N3 B1 N1 104.0(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C13 1.420(5) .
O1 C13 1.420(5) 8_565
O1 B1 1.456(7) .
N1 C4 1.373(5) .
N1 C4 1.373(5) 8_565
N1 B1 1.494(7) .
N2 C4 1.346(5) .
N2 C5 1.353(5) .
N3 C12 1.375(5) .
N3 C5 1.375(5) .
N3 B1 1.492(5) .
N4 C12 1.343(5) .
N4 C12 1.343(5) 8_565
C1 C1 1.387(8) 8_565
C1 C2 1.387(5) .
C2 C3 1.398(5) .
C3 C3 1.417(8) 8_565
C3 C4 1.458(5) .
C5 C6 1.451(5) .
C6 C7 1.386(6) .
C6 C11 1.425(6) .
C7 C8 1.385(6) .
C8 C9 1.398(7) .
C9 C10 1.370(7) .
C10 C11 1.396(6) .
C11 C12 1.448(6) .
C13 C14 1.3900 .
C13 C18 1.3900 .
C14 C15 1.3900 .
C15 C16 1.3900 .
C16 C17 1.3900 .
C17 C18 1.3900 .
C17 C22 1.3900 .
C18 C19 1.3900 .
C19 C20 1.3900 .
C20 C21 1.3900 .
C21 C22 1.3900 .
B1 N3 1.492(5) 8_565
