#------------------------------------------------------------------------------
#$Date: 2017-02-04 03:15:11 +0200 (Sat, 04 Feb 2017) $
#$Revision: 191285 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/08/69/4086978.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_4086978
loop_
_publ_author_name
'Wang, Zikuan'
'Fu, Xuefeng'
_publ_section_title
;
 Synthesis, Characterization, and Reactivity Studies of Subphthalocyanine
 Boron Triflate
;
_journal_issue                   2
_journal_name_full               Organometallics
_journal_page_first              285
_journal_paper_doi               10.1021/acs.organomet.6b00754
_journal_volume                  36
_journal_year                    2017
_chemical_formula_moiety         'C25 H15 B N6'
_chemical_formula_sum            'C25 H15 B N6'
_chemical_formula_weight         410.24
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_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
_audit_creation_date             2015-05-08
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.537(2)
_cell_length_b                   15.918(3)
_cell_length_c                   11.484(2)
_cell_measurement_reflns_used    6251
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4696
_cell_measurement_theta_min      1.2793
_cell_volume                     1926.2(6)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_structure_solution
;
'SHELXT (Sheldrick, 2014)'

;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
scan:
    Number of images: 360
               Slice: -110.0000 - 70.0000
         Image width: 0.5000
            Exp time: 3.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 180.0000
                 XTD: 45.2851
              2theta: -20.0759
scan:
    Number of images: 282
               Slice: -101.0000 - 40.0000
         Image width: 0.5000
            Exp time: 3.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 0.0000
                 XTD: 45.2851
              2theta: -20.0759
;
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0150
_diffrn_orient_matrix_UB_12      -0.0651
_diffrn_orient_matrix_UB_13      0.0674
_diffrn_orient_matrix_UB_21      0.0817
_diffrn_orient_matrix_UB_22      0.0285
_diffrn_orient_matrix_UB_23      0.0093
_diffrn_orient_matrix_UB_31      -0.0192
_diffrn_orient_matrix_UB_32      0.0408
_diffrn_orient_matrix_UB_33      0.0437
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13197
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.472
_diffrn_reflns_theta_min         2.559
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0000
_diffrn_source_power             1.2000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8518
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.605
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.164
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     152
_refine_ls_number_reflns         2278
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.164
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0575
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0540P)²+1.6004P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1403
_refine_ls_wR_factor_ref         0.1409
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2248
_reflns_number_total             2278
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            om6b00754_si_002.cif
_cod_data_source_block           (subPc)BMe
_cod_original_cell_volume        1926.1(7)
_cod_database_code               4086978
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_diffrn_number_total             2523
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H13A(0.5) H13B(0.5) H13C(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C12(H12)
3.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, 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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.5833(2) 0.2500 -0.01102(18) 0.0245(4) Uani 1 2 d S T P . .
N2 N 0.47858(13) 0.32394(9) 0.14135(12) 0.0220(3) Uani 1 1 d . . . . .
N3 N 0.47593(14) 0.39523(9) 0.32353(13) 0.0243(3) Uani 1 1 d . . . . .
N4 N 0.42167(19) 0.2500 0.31162(18) 0.0225(4) Uani 1 2 d S T P . .
C1 C 0.55314(16) 0.32181(11) 0.04403(14) 0.0229(4) Uani 1 1 d . . . . .
C2 C 0.61241(16) 0.40396(11) 0.03591(15) 0.0241(4) Uani 1 1 d . . . . .
C3 C 0.69538(17) 0.43898(12) -0.04573(16) 0.0291(4) Uani 1 1 d . . . . .
H3 H 0.7184 0.4092 -0.1121 0.035 Uiso 1 1 calc R . . . .
C4 C 0.74220(17) 0.51837(12) -0.02587(17) 0.0308(4) Uani 1 1 d . . . . .
H4 H 0.7956 0.5432 -0.0805 0.037 Uiso 1 1 calc R . . . .
C5 C 0.70996(18) 0.56267(12) 0.07679(18) 0.0338(4) Uani 1 1 d . . . . .
H5 H 0.7423 0.6164 0.0883 0.041 Uiso 1 1 calc R . . . .
C6 C 0.63104(17) 0.52772(11) 0.16073(16) 0.0280(4) Uani 1 1 d . . . . .
H6 H 0.6128 0.5563 0.2293 0.034 Uiso 1 1 calc R . . . .
C7 C 0.58017(16) 0.44870(11) 0.13909(15) 0.0243(4) Uani 1 1 d . . . . .
C8 C 0.50041(16) 0.39308(10) 0.20862(15) 0.0230(4) Uani 1 1 d . . . . .
C9 C 0.44484(16) 0.32158(11) 0.37365(15) 0.0237(4) Uani 1 1 d . . . . .
C10 C 0.46391(16) 0.29485(11) 0.49389(15) 0.0253(4) Uani 1 1 d . . . . .
C11 C 0.49405(17) 0.33942(12) 0.59394(15) 0.0276(4) Uani 1 1 d . . . . .
H11 H 0.4964 0.3978 0.5938 0.033 Uiso 1 1 calc R . . . .
C12 C 0.52065(19) 0.29392(13) 0.69439(16) 0.0333(4) Uani 1 1 d . . . . .
H12 H 0.5388 0.3225 0.7630 0.040 Uiso 1 1 calc R . . . .
C13 C 0.2548(2) 0.2500 0.1434(2) 0.0280(5) Uani 1 2 d S T P . .
H13A H 0.2116 0.2959 0.1803 0.042 Uiso 0.5 1 calc GR . . A -1
H13B H 0.2160 0.1980 0.1662 0.042 Uiso 0.5 1 calc GR . . A -1
H13C H 0.2495 0.2561 0.0604 0.042 Uiso 0.5 1 calc GR . . A -1
B1 B 0.3996(3) 0.2500 0.1819(2) 0.0219(5) Uani 1 2 d S T P . .
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'
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
C1 N1 C1 116.5(2) 7_565 .
C1 N2 B1 123.24(15) . .
C8 N2 C1 112.71(14) . .
C8 N2 B1 123.05(15) . .
C8 N3 C9 116.35(15) . .
C9 N4 C9 113.1(2) 7_565 .
C9 N4 B1 122.88(10) . .
C9 N4 B1 122.88(10) 7_565 .
N1 C1 N2 122.79(16) . .
N1 C1 C2 129.33(16) . .
N2 C1 C2 106.11(14) . .
C3 C2 C1 132.15(16) . .
C3 C2 C7 120.54(16) . .
C7 C2 C1 107.12(15) . .
C2 C3 H3 120.7 . .
C4 C3 C2 118.65(18) . .
C4 C3 H3 120.7 . .
C3 C4 H4 119.7 . .
C3 C4 C5 120.64(17) . .
C5 C4 H4 119.7 . .
C4 C5 H5 119.3 . .
C6 C5 C4 121.48(17) . .
C6 C5 H5 119.3 . .
C5 C6 H6 121.0 . .
C5 C6 C7 117.99(17) . .
C7 C6 H6 121.0 . .
C2 C7 C8 106.83(15) . .
C6 C7 C2 120.63(16) . .
C6 C7 C8 132.36(17) . .
N2 C8 C7 106.07(15) . .
N3 C8 N2 122.94(16) . .
N3 C8 C7 129.21(16) . .
N3 C9 N4 123.15(16) . .
N3 C9 C10 128.69(16) . .
N4 C9 C10 105.97(15) . .
C10 C10 C9 106.96(10) 7_565 .
C11 C10 C9 131.79(17) . .
C11 C10 C10 120.76(11) . 7_565
C10 C11 H11 121.1 . .
C10 C11 C12 117.83(18) . .
C12 C11 H11 121.1 . .
C11 C12 C12 121.39(11) . 7_565
C11 C12 H12 119.3 . .
C12 C12 H12 119.3 7_565 .
H13A C13 H13B 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
B1 C13 H13A 109.5 . .
B1 C13 H13B 109.5 . .
B1 C13 H13C 109.5 . .
N2 B1 N2 101.97(19) 7_565 .
N2 B1 C13 116.22(14) 7_565 .
N2 B1 C13 116.22(14) . .
N4 B1 N2 102.67(14) . 7_565
N4 B1 N2 102.67(14) . .
N4 B1 C13 115.0(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C1 1.344(2) 7_565
N1 C1 1.344(2) .
N2 C1 1.367(2) .
N2 C8 1.364(2) .
N2 B1 1.515(2) .
N3 C8 1.345(2) .
N3 C9 1.347(2) .
N4 C9 1.366(2) .
N4 C9 1.366(2) 7_565
N4 B1 1.507(3) .
C1 C2 1.452(2) .
C2 C3 1.398(2) .
C2 C7 1.424(2) .
C3 H3 0.9300 .
C3 C4 1.376(3) .
C4 H4 0.9300 .
C4 C5 1.415(3) .
C5 H5 0.9300 .
C5 C6 1.389(3) .
C6 H6 0.9300 .
C6 C7 1.390(2) .
C7 C8 1.459(2) .
C9 C10 1.459(2) .
C10 C10 1.428(4) 7_565
C10 C11 1.387(2) .
C11 H11 0.9300 .
C11 C12 1.391(3) .
C12 C12 1.398(4) 7_565
C12 H12 0.9300 .
C13 H13A 0.9600 .
C13 H13B 0.9600 .
C13 H13C 0.9600 .
C13 B1 1.589(4) .
B1 N2 1.515(2) 7_565
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
N1 C1 C2 C3 16.6(3) . .
N1 C1 C2 C7 -158.25(19) . .
N2 C1 C2 C3 -178.52(18) . .
N2 C1 C2 C7 6.65(18) . .
N3 C9 C10 C10 -157.22(15) . 7_565
N3 C9 C10 C11 14.5(3) . .
N4 C9 C10 C10 6.08(14) . 7_565
N4 C9 C10 C11 177.80(19) . .
C1 N1 C1 N2 -10.0(3) 7_565 .
C1 N1 C1 C2 152.65(14) 7_565 .
C1 N2 C8 N3 -155.30(16) . .
C1 N2 C8 C7 10.76(19) . .
C1 N2 B1 N2 31.1(3) . 7_565
C1 N2 B1 N4 137.25(16) . .
C1 N2 B1 C13 -96.3(2) . .
C1 C2 C3 C4 -176.10(18) . .
C1 C2 C7 C6 175.24(15) . .
C1 C2 C7 C8 -0.44(18) . .
C2 C3 C4 C5 1.8(3) . .
C2 C7 C8 N2 -5.93(18) . .
C2 C7 C8 N3 158.94(17) . .
C3 C2 C7 C6 -0.3(3) . .
C3 C2 C7 C8 -176.00(16) . .
C3 C4 C5 C6 0.3(3) . .
C4 C5 C6 C7 -2.4(3) . .
C5 C6 C7 C2 2.4(3) . .
C5 C6 C7 C8 176.81(18) . .
C6 C7 C8 N2 179.10(17) . .
C6 C7 C8 N3 -16.0(3) . .
C7 C2 C3 C4 -1.8(3) . .
C8 N2 C1 N1 155.08(18) . .
C8 N2 C1 C2 -11.04(19) . .
C8 N2 B1 N2 -136.55(14) . 7_565
C8 N2 B1 N4 -30.4(2) . .
C8 N2 B1 C13 96.0(2) . .
C8 N3 C9 N4 -8.8(2) . .
C8 N3 C9 C10 151.96(17) . .
C9 N3 C8 N2 9.0(2) . .
C9 N3 C8 C7 -153.61(17) . .
C9 N4 C9 N3 153.87(13) 7_565 .
C9 N4 C9 C10 -10.6(2) 7_565 .
C9 N4 B1 N2 -30.6(3) 7_565 7_565
C9 N4 B1 N2 30.6(3) . .
C9 N4 B1 N2 -136.21(17) 7_565 .
C9 N4 B1 N2 136.21(17) . 7_565
C9 N4 B1 C13 96.58(18) 7_565 .
C9 N4 B1 C13 -96.58(18) . .
C9 C10 C11 C12 -172.51(17) . .
C10 C10 C11 C12 -1.7(2) 7_565 .
C10 C11 C12 C12 1.7(2) . 7_565
B1 N2 C1 N1 -13.7(3) . .
B1 N2 C1 C2 -179.87(16) . .
B1 N2 C8 N3 13.6(3) . .
B1 N2 C8 C7 179.61(16) . .
B1 N4 C9 N3 -14.1(3) . .
B1 N4 C9 C10 -178.59(19) . .
