#------------------------------------------------------------------------------
#$Date: 2024-09-04 05:04:42 +0300 (Wed, 04 Sep 2024) $
#$Revision: 294359 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/26/2312601.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_2312601
loop_
_publ_author_name
'Zigelstein, Rachel'
'Lough, Alan J.'
'Bender, Timothy P.'
_publ_section_title
;
 The influence of the axial group on the crystal structures of boron
 subphthalocyanines.
;
_journal_coeditor_code           DG3059
_journal_issue                   10
_journal_name_full
'Acta crystallographica. Section C, Structural chemistry'
_journal_paper_doi               10.1107/S2053229624006934
_journal_volume                  80
_journal_year                    2024
_chemical_formula_iupac          'C25 H15 B N6 O'
_chemical_formula_moiety         'C25 H15 B N6 O'
_chemical_formula_sum            'C25 H15 B N6 O'
_chemical_formula_weight         426.24
_chemical_name_systematic
;
(Methanolato)(subphthalocyaninato)boron
;
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2019/1
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.3162(11)
_cell_length_b                   15.2325(19)
_cell_length_c                   10.4151(10)
_cell_measurement_reflns_used    8333
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      65.51
_cell_measurement_theta_min      5.14
_cell_volume                     1953.9(4)
_computing_cell_refinement
;
APEX4 (Bruker, 2021)
;
_computing_data_collection
;
APEX4 (Bruker, 2021)
;
_computing_data_reduction
;
APEX4 (Bruker, 2021)
;
_computing_molecular_graphics
;
PLATON (Spek, 2020)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2019 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2018 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CMOs PHOTON II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0570
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            27808
_diffrn_reflns_theta_full        65.987
_diffrn_reflns_theta_max         65.987
_diffrn_reflns_theta_min         5.144
_diffrn_source                   'Icoatec ImuS with multi-layer optics'
_exptl_absorpt_coefficient_mu    0.745
_exptl_absorpt_correction_T_max  0.7527
_exptl_absorpt_correction_T_min  0.6589
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            pink
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_description       Shard
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.186
_refine_ls_extinction_coef       0.0026(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2019 (Sheldrick, 2015b)
;
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         1762
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0321
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0301P)²+0.6842P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0749
_refine_ls_wR_factor_ref         0.0778
_reflns_number_gt                1570
_reflns_number_total             1762
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            dg3059.cif
_cod_data_source_block           d2368_a
_cod_database_code               2312601
_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.
;
_shelx_estimated_absorpt_t_min   0.929
_shelx_estimated_absorpt_t_max   0.985
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_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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.74991(10) 0.750000 0.29681(12) 0.0284(3) Uani d 1 . .
N N1 0.96403(12) 0.750000 0.56717(14) 0.0249(3) Uani d 1 . .
N N2 0.80691(8) 0.67267(7) 0.49738(10) 0.0235(3) Uani d 1 . .
N N3 0.64054(8) 0.59780(7) 0.53777(10) 0.0266(3) Uani d 1 . .
N N4 0.64148(12) 0.750000 0.48741(14) 0.0248(3) Uani d 1 . .
C C1 0.90890(10) 0.67473(8) 0.54862(12) 0.0235(3) Uani d 1 . .
C C2 0.92753(10) 0.58766(8) 0.60186(12) 0.0240(3) Uani d 1 . .
C C3 1.01583(10) 0.55147(8) 0.66539(13) 0.0281(3) Uani d 1 . .
H H3A 1.081703 0.583335 0.674325 0.034 Uiso calc 1 . .
C C4 1.00543(11) 0.46789(9) 0.71533(13) 0.0316(3) Uani d 1 . .
H H4A 1.065143 0.442124 0.759076 0.038 Uiso calc 1 . .
C C5 0.90876(11) 0.42036(9) 0.70283(13) 0.0306(3) Uani d 1 . .
H H5A 0.904612 0.362429 0.736277 0.037 Uiso calc 1 . .
C C6 0.81926(10) 0.45637(8) 0.64260(13) 0.0276(3) Uani d 1 . .
H H6A 0.753201 0.424472 0.636119 0.033 Uiso calc 1 . .
C C7 0.82830(10) 0.54053(8) 0.59167(12) 0.0245(3) Uani d 1 . .
C C8 0.74954(10) 0.59952(8) 0.53308(12) 0.0246(3) Uani d 1 . .
C C9 0.58841(10) 0.67493(8) 0.52199(12) 0.0251(3) Uani d 1 . .
C C10 0.48053(10) 0.70324(9) 0.56126(12) 0.0274(3) Uani d 1 . .
C C11 0.38841(10) 0.65651(10) 0.59870(13) 0.0332(3) Uani d 1 . .
H H11 0.388003 0.594147 0.599794 0.040 Uiso calc 1 . .
C C12 0.29788(11) 0.70410(11) 0.63409(15) 0.0406(4) Uani d 1 . .
H H12 0.233924 0.673711 0.659092 0.049 Uiso calc 1 . .
C C13 0.84839(16) 0.750000 0.23075(18) 0.0316(4) Uani d 1 . .
H H13A 0.836530 0.729920 0.142465 0.047 Uiso calc 0.5 . .
H H13B 0.899536 0.710471 0.273802 0.047 Uiso calc 0.5 . .
H H13C 0.878312 0.809608 0.229560 0.047 Uiso calc 0.5 . .
B B1 0.75398(16) 0.750000 0.43343(19) 0.0240(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 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C13 O1 B1 . . 117.55(15) ?
C1 N1 C1 7_575 . 116.76(15) ?
C1 N2 C8 . . 112.76(10) ?
C1 N2 B1 . . 123.69(11) ?
C8 N2 B1 . . 122.28(11) ?
C8 N3 C9 . . 117.01(11) ?
C9 N4 C9 . 7_575 113.74(15) ?
C9 N4 B1 . . 122.87(7) ?
C9 N4 B1 7_575 . 122.87(7) ?
N1 C1 N2 . . 122.66(11) ?
N1 C1 C2 . . 129.92(12) ?
N2 C1 C2 . . 105.85(10) ?
C3 C2 C7 . . 120.59(11) ?
C3 C2 C1 . . 131.86(12) ?
C7 C2 C1 . . 107.23(11) ?
C4 C3 C2 . . 118.24(12) ?
C4 C3 H3A . . 120.9 ?
C2 C3 H3A . . 120.9 ?
C3 C4 C5 . . 121.38(12) ?
C3 C4 H4A . . 119.3 ?
C5 C4 H4A . . 119.3 ?
C6 C5 C4 . . 121.03(12) ?
C6 C5 H5A . . 119.5 ?
C4 C5 H5A . . 119.5 ?
C5 C6 C7 . . 118.34(12) ?
C5 C6 H6A . . 120.8 ?
C7 C6 H6A . . 120.8 ?
C6 C7 C2 . . 120.37(12) ?
C6 C7 C8 . . 132.43(12) ?
C2 C7 C8 . . 107.00(11) ?
N3 C8 N2 . . 122.73(11) ?
N3 C8 C7 . . 129.67(11) ?
N2 C8 C7 . . 105.77(10) ?
N3 C9 N4 . . 122.25(11) ?
N3 C9 C10 . . 131.17(12) ?
N4 C9 C10 . . 105.25(11) ?
C11 C10 C10 . 7_575 120.68(8) ?
C11 C10 C9 . . 132.06(13) ?
C10 C10 C9 7_575 . 107.23(7) ?
C12 C11 C10 . . 117.63(14) ?
C12 C11 H11 . . 121.2 ?
C10 C11 H11 . . 121.2 ?
C11 C12 C12 . 7_575 121.69(9) ?
C11 C12 H12 . . 119.2 ?
C12 C12 H12 7_575 . 119.2 ?
O1 C13 H13A . . 109.5 ?
O1 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
O1 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
O1 C13 H13A . 7_575 109.5(2) ?
H13A C13 H13A . 7_575 36.4 ?
H13B C13 H13A . 7_575 135.8 ?
H13C C13 H13A . 7_575 75.8 ?
O1 C13 H13B . 7_575 109.5(3) ?
H13A C13 H13B . 7_575 135.8 ?
H13B C13 H13B . 7_575 75.8 ?
H13C C13 H13B . 7_575 36.4 ?
H13A C13 H13B 7_575 7_575 109.5 ?
O1 C13 H13C . 7_575 109.47(12) ?
H13A C13 H13C . 7_575 75.8 ?
H13B C13 H13C . 7_575 36.4 ?
H13C C13 H13C . 7_575 135.8 ?
H13A C13 H13C 7_575 7_575 109.5 ?
H13B C13 H13C 7_575 7_575 109.5 ?
O1 B1 N4 . . 110.07(15) ?
O1 B1 N2 . . 117.29(10) ?
N4 B1 N2 . . 103.62(11) ?
O1 B1 N2 . 7_575 117.28(10) ?
N4 B1 N2 . 7_575 103.62(11) ?
N2 B1 N2 . 7_575 103.30(14) ?
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 C13 . 1.394(2) ?
O1 B1 . 1.424(2) ?
N1 C1 7_575 1.3465(14) ?
N1 C1 . 1.3466(14) ?
N2 C1 . 1.3651(16) ?
N2 C8 . 1.3708(16) ?
N2 B1 . 1.5020(16) ?
N3 C8 . 1.3435(16) ?
N3 C9 . 1.3489(17) ?
N4 C9 . 1.3655(15) ?
N4 C9 7_575 1.3656(15) ?
N4 B1 . 1.495(2) ?
C1 C2 . 1.4556(17) ?
C2 C3 . 1.3872(18) ?
C2 C7 . 1.4213(17) ?
C3 C4 . 1.3813(19) ?
C3 H3A . 0.9500 ?
C4 C5 . 1.3995(19) ?
C4 H4A . 0.9500 ?
C5 C6 . 1.3819(19) ?
C5 H5A . 0.9500 ?
C6 C7 . 1.3920(18) ?
C6 H6A . 0.9500 ?
C7 C8 . 1.4563(18) ?
C9 C10 . 1.4555(18) ?
C10 C11 . 1.3950(18) ?
C10 C10 7_575 1.425(3) ?
C11 C12 . 1.380(2) ?
C11 H11 . 0.9500 ?
C12 C12 7_575 1.398(3) ?
C12 H12 . 0.9500 ?
C13 H13A . 0.9800 ?
C13 H13B . 0.9800 ?
C13 H13C . 0.9800 ?
C13 H13A 7_575 0.980(9) ?
C13 H13B 7_575 0.980(15) ?
C13 H13C 7_575 0.980(5) ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C1 N1 C1 N2 7_575 . . . 8.5(2) ?
C1 N1 C1 C2 7_575 . . . -155.07(10) ?
C8 N2 C1 N1 . . . . -155.14(13) ?
B1 N2 C1 N1 . . . . 12.2(2) ?
C8 N2 C1 C2 . . . . 11.82(13) ?
B1 N2 C1 C2 . . . . 179.17(12) ?
N1 C1 C2 C3 . . . . -14.3(2) ?
N2 C1 C2 C3 . . . . -179.94(13) ?
N1 C1 C2 C7 . . . . 159.10(13) ?
N2 C1 C2 C7 . . . . -6.56(13) ?
C7 C2 C3 C4 . . . . 1.61(18) ?
C1 C2 C3 C4 . . . . 174.26(13) ?
C2 C3 C4 C5 . . . . -0.04(19) ?
C3 C4 C5 C6 . . . . -1.6(2) ?
C4 C5 C6 C7 . . . . 1.55(19) ?
C5 C6 C7 C2 . . . . 0.02(18) ?
C5 C6 C7 C8 . . . . -174.12(13) ?
C3 C2 C7 C6 . . . . -1.63(18) ?
C1 C2 C7 C6 . . . . -175.90(11) ?
C3 C2 C7 C8 . . . . 173.85(11) ?
C1 C2 C7 C8 . . . . -0.42(13) ?
C9 N3 C8 N2 . . . . -8.48(17) ?
C9 N3 C8 C7 . . . . 153.85(13) ?
C1 N2 C8 N3 . . . . 153.87(11) ?
B1 N2 C8 N3 . . . . -13.69(18) ?
C1 N2 C8 C7 . . . . -12.08(13) ?
B1 N2 C8 C7 . . . . -179.64(12) ?
C6 C7 C8 N3 . . . . 17.3(2) ?
C2 C7 C8 N3 . . . . -157.40(13) ?
C6 C7 C8 N2 . . . . -178.07(13) ?
C2 C7 C8 N2 . . . . 7.22(13) ?
C8 N3 C9 N4 . . . . 7.75(18) ?
C8 N3 C9 C10 . . . . -157.04(13) ?
C9 N4 C9 N3 7_575 . . . -156.56(9) ?
B1 N4 C9 N3 . . . . 15.4(2) ?
C9 N4 C9 C10 7_575 . . . 11.64(19) ?
B1 N4 C9 C10 . . . . -176.44(14) ?
N3 C9 C10 C11 . . . . -17.8(2) ?
N4 C9 C10 C11 . . . . 175.53(14) ?
N3 C9 C10 C10 . . . 7_575 160.09(12) ?
N4 C9 C10 C10 . . . 7_575 -6.63(11) ?
C10 C10 C11 C12 7_575 . . . 0.65(15) ?
C9 C10 C11 C12 . . . . 178.25(13) ?
C10 C11 C12 C12 . . . 7_575 -0.66(15) ?
C13 O1 B1 N4 . . . . 180.000000 ?
C13 O1 B1 N2 . . . . -61.93(13) ?
C13 O1 B1 N2 . . . 7_575 61.93(13) ?
C9 N4 B1 O1 . . . . 94.40(13) ?
C9 N4 B1 O1 7_575 . . . -94.40(13) ?
C9 N4 B1 N2 . . . . -31.80(19) ?
C9 N4 B1 N2 7_575 . . . 139.39(12) ?
C9 N4 B1 N2 . . . 7_575 -139.39(12) ?
C9 N4 B1 N2 7_575 . . 7_575 31.80(19) ?
C1 N2 B1 O1 . . . . 103.19(15) ?
C8 N2 B1 O1 . . . . -90.62(17) ?
C1 N2 B1 N4 . . . . -135.32(12) ?
C8 N2 B1 N4 . . . . 30.86(16) ?
C1 N2 B1 N2 . . . 7_575 -27.49(19) ?
C8 N2 B1 N2 . . . 7_575 138.69(10) ?
