#------------------------------------------------------------------------------
#$Date: 2020-07-06 05:04:07 +0300 (Mon, 06 Jul 2020) $
#$Revision: 253820 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/65/7126591.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_7126591
loop_
_publ_author_name
'Schrage, Briana R.'
'Nemykin, Victor N.'
'Ziegler, Christopher J.'
_publ_section_title
;
 Biliazine: a ring open phthalocyanine analog with a meso hydrogen bond.
;
_journal_issue                   49
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              6628
_journal_page_last               6631
_journal_paper_doi               10.1039/d0cc03060k
_journal_volume                  56
_journal_year                    2020
_chemical_formula_sum            'C24 H21 Co N9 O2'
_chemical_formula_weight         526.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2020-03-06 deposited with the CCDC.	2020-05-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.251(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.8635(3)
_cell_length_b                   23.0498(13)
_cell_length_c                   14.1576(8)
_cell_measurement_reflns_used    6022
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.64
_cell_measurement_theta_min      3.73
_cell_volume                     2188.8(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 'ACTA 50'
_diffrn_measured_fraction_theta_max 0.860
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0529
_diffrn_reflns_av_unetI/netI     0.0539
_diffrn_reflns_Laue_measured_fraction_full 0.860
_diffrn_reflns_Laue_measured_fraction_max 0.860
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            11209
_diffrn_reflns_point_group_measured_fraction_full 0.860
_diffrn_reflns_point_group_measured_fraction_max 0.860
_diffrn_reflns_theta_full        'ACTA 50'
_diffrn_reflns_theta_max         66.631
_diffrn_reflns_theta_min         3.726
_exptl_absorpt_coefficient_mu    6.531
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5108
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.598
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1084
_exptl_crystal_size_max          0.587
_exptl_crystal_size_mid          0.122
_exptl_crystal_size_min          0.066
_refine_diff_density_max         0.532
_refine_diff_density_min         -0.486
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         3325
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0468
_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)+(0.0689P)²+0.9247P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1159
_refine_ls_wR_factor_ref         0.1228
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2784
_reflns_number_total             3325
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc03060k2.cif
_cod_data_source_block           Co(BlzH)(MeOH)2
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7126588--7126592.cif.
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7126591
_shelx_shelxl_version_number     2016/6
_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. 
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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_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
C1 C 0.7744(5) 0.21809(16) 0.4864(3) 0.0259(8) Uani 1 1 d . . . . .
H1 H 0.763332 0.189751 0.436797 0.031 Uiso 1 1 calc R U . . .
C2 C 0.9380(5) 0.22587(15) 0.5596(2) 0.0233(8) Uani 1 1 d . . . . .
H2 H 1.059385 0.204631 0.571445 0.028 Uiso 1 1 calc R U . . .
C3 C 0.8853(5) 0.27252(15) 0.6133(2) 0.0212(8) Uani 1 1 d . . . . .
C4 C 0.9461(5) 0.33657(15) 0.7436(2) 0.0191(8) Uani 1 1 d . . . . .
C5 C 1.0697(5) 0.36005(15) 0.8337(3) 0.0199(8) Uani 1 1 d . . . . .
C6 C 1.2620(5) 0.34904(14) 0.8851(2) 0.0216(8) Uani 1 1 d . . . . .
H6 H 1.345452 0.321856 0.862331 0.026 Uiso 1 1 calc R U . . .
C7 C 1.3280(5) 0.37909(15) 0.9707(3) 0.0239(8) Uani 1 1 d . . . . .
H7 H 1.459930 0.372796 1.006414 0.029 Uiso 1 1 calc R U . . .
C8 C 1.2056(5) 0.41838(16) 1.0057(2) 0.0242(8) Uani 1 1 d . . . . .
H8 H 1.253766 0.437604 1.065467 0.029 Uiso 1 1 calc R U . . .
C9 C 1.0139(5) 0.42952(15) 0.9538(2) 0.0219(8) Uani 1 1 d . . . . .
H9 H 0.929394 0.456289 0.976707 0.026 Uiso 1 1 calc R U . . .
C10 C 0.9506(5) 0.40046(14) 0.8680(2) 0.0192(8) Uani 1 1 d . . . . .
C11 C 0.7611(5) 0.40235(14) 0.7978(2) 0.0181(7) Uani 1 1 d . . . . .
C12 C 0.4455(5) 0.44127(14) 0.7488(2) 0.0197(7) Uani 1 1 d . . . . .
C13 C 0.2949(5) 0.48375(15) 0.7634(3) 0.0205(8) Uani 1 1 d . . . . .
C14 C 0.2983(5) 0.52702(15) 0.8315(3) 0.0235(8) Uani 1 1 d . . . . .
H14 H 0.411646 0.533057 0.882172 0.028 Uiso 1 1 calc R U . . .
C15 C 0.1278(5) 0.56144(16) 0.8225(3) 0.0249(8) Uani 1 1 d . . . . .
H15 H 0.125110 0.592027 0.867148 0.030 Uiso 1 1 calc R U . . .
C16 C -0.0388(5) 0.55133(15) 0.7483(3) 0.0244(8) Uani 1 1 d . . . . .
H16 H -0.153513 0.575049 0.744078 0.029 Uiso 1 1 calc R U . . .
C17 C -0.0410(5) 0.50785(15) 0.6813(3) 0.0236(8) Uani 1 1 d . . . . .
H17 H -0.155101 0.501074 0.631346 0.028 Uiso 1 1 calc R U . . .
C18 C 0.1306(5) 0.47419(14) 0.6895(2) 0.0192(7) Uani 1 1 d . . . . .
C19 C 0.1843(5) 0.42713(14) 0.6303(2) 0.0185(7) Uani 1 1 d . . . . .
C20 C 0.1199(5) 0.36464(15) 0.4980(2) 0.0197(7) Uani 1 1 d . . . . .
C21 C 0.0000(5) 0.34313(14) 0.4132(3) 0.0230(8) Uani 1 1 d . . . . .
H21 H -0.131898 0.354703 0.384171 0.028 Uiso 1 1 calc R U . . .
C22 C 0.1127(5) 0.30197(16) 0.3810(3) 0.0252(8) Uani 1 1 d . . . . .
H22 H 0.073056 0.279470 0.323956 0.030 Uiso 1 1 calc R U . . .
C23 C 0.5549(5) 0.43330(18) 0.4335(3) 0.0338(9) Uani 1 1 d . . . . .
H23A H 0.562381 0.399716 0.392016 0.051 Uiso 1 1 calc R U . . .
H23B H 0.622725 0.466407 0.411287 0.051 Uiso 1 1 calc R U . . .
H23C H 0.414858 0.443191 0.430534 0.051 Uiso 1 1 calc R U . . .
C24 C 0.4830(5) 0.21887(16) 0.7126(3) 0.0313(9) Uani 1 1 d . . . . .
H24A H 0.439550 0.203875 0.646686 0.047 Uiso 1 1 calc R U . . .
H24B H 0.421077 0.196079 0.756766 0.047 Uiso 1 1 calc R U . . .
H24C H 0.628357 0.215930 0.732375 0.047 Uiso 1 1 calc R U . . .
Co1 Co 0.53380(7) 0.34940(2) 0.61967(4) 0.0186(2) Uani 1 1 d . . . . .
N1 N 0.6314(4) 0.25653(13) 0.4950(2) 0.0251(7) Uani 1 1 d . . . . .
N2 N 0.6965(4) 0.29025(12) 0.5733(2) 0.0203(6) Uani 1 1 d . . . . .
N3 N 1.0051(4) 0.29564(12) 0.6942(2) 0.0209(6) Uani 1 1 d . . . . .
N4 N 0.7585(4) 0.36402(12) 0.7251(2) 0.0194(6) Uani 1 1 d . . . . .
N5 N 0.6209(4) 0.43936(12) 0.81168(19) 0.0200(6) Uani 1 1 d . . . . .
N6 N 0.3805(4) 0.40844(12) 0.6702(2) 0.0200(6) Uani 1 1 d . . . . .
N7 N 0.0648(4) 0.40789(12) 0.5541(2) 0.0198(6) Uani 1 1 d . . . . .
N8 N 0.2983(4) 0.33713(12) 0.5164(2) 0.0209(6) Uani 1 1 d . . . . .
N9 N 0.2884(4) 0.29856(12) 0.4432(2) 0.0224(7) Uani 1 1 d . . . . .
H9A H 0.384842 0.274524 0.437402 0.027 Uiso 1 1 calc R U . . .
O1 O 0.6487(4) 0.41969(11) 0.53024(17) 0.0249(6) Uani 1 1 d . . . . .
O2 O 0.4243(4) 0.27833(10) 0.71535(18) 0.0249(6) Uani 1 1 d . . . . .
H25 H 0.296(8) 0.280(2) 0.709(4) 0.072(17) Uiso 1 1 d . . . . .
H26 H 0.769(8) 0.417(2) 0.537(4) 0.072(18) Uiso 1 1 d . . . . .
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'
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'
Co Co -2.3653 3.6143 '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
_geom_angle_publ_flag
N1 C1 C2 110.0(3) . . ?
C1 C2 C3 104.2(3) . . ?
N2 C3 N3 125.5(3) . . ?
N2 C3 C2 109.6(3) . . ?
N3 C3 C2 124.9(3) . . ?
N3 C4 N4 127.4(3) . . ?
N3 C4 C5 123.2(3) . . ?
N4 C4 C5 109.4(3) . . ?
C6 C5 C10 120.2(3) . . ?
C6 C5 C4 133.9(3) . . ?
C10 C5 C4 105.9(3) . . ?
C7 C6 C5 117.7(3) . . ?
C6 C7 C8 121.7(3) . . ?
C9 C8 C7 120.4(3) . . ?
C10 C9 C8 117.7(3) . . ?
C9 C10 C5 122.3(3) . . ?
C9 C10 C11 130.9(3) . . ?
C5 C10 C11 106.7(3) . . ?
N5 C11 N4 129.6(3) . . ?
N5 C11 C10 119.1(3) . . ?
N4 C11 C10 111.3(3) . . ?
N5 C12 N6 128.9(3) . . ?
N5 C12 C13 119.3(3) . . ?
N6 C12 C13 111.9(3) . . ?
C14 C13 C18 122.2(3) . . ?
C14 C13 C12 132.1(3) . . ?
C18 C13 C12 105.8(3) . . ?
C13 C14 C15 117.1(3) . . ?
C14 C15 C16 120.7(3) . . ?
C17 C16 C15 121.7(3) . . ?
C16 C17 C18 117.5(3) . . ?
C13 C18 C17 120.9(3) . . ?
C13 C18 C19 106.7(3) . . ?
C17 C18 C19 132.4(3) . . ?
N7 C19 N6 127.9(3) . . ?
N7 C19 C18 122.8(3) . . ?
N6 C19 C18 109.4(3) . . ?
N8 C20 N7 125.2(3) . . ?
N8 C20 C21 110.1(3) . . ?
N7 C20 C21 124.7(3) . . ?
C22 C21 C20 105.2(3) . . ?
N9 C22 C21 108.5(3) . . ?
N4 Co1 N6 89.97(11) . . ?
N4 Co1 N8 177.07(12) . . ?
N6 Co1 N8 87.14(11) . . ?
N4 Co1 N2 87.81(11) . . ?
N6 Co1 N2 177.76(11) . . ?
N8 Co1 N2 95.07(11) . . ?
N4 Co1 O1 89.52(10) . . ?
N6 Co1 O1 89.13(11) . . ?
N8 Co1 O1 90.92(11) . . ?
N2 Co1 O1 91.12(10) . . ?
N4 Co1 O2 88.67(10) . . ?
N6 Co1 O2 90.68(10) . . ?
N8 Co1 O2 90.88(10) . . ?
N2 Co1 O2 89.00(10) . . ?
O1 Co1 O2 178.18(9) . . ?
C1 N1 N2 109.4(3) . . ?
N1 N2 C3 106.7(3) . . ?
N1 N2 Co1 124.2(2) . . ?
C3 N2 Co1 129.0(2) . . ?
C4 N3 C3 122.4(3) . . ?
C11 N4 C4 106.7(3) . . ?
C11 N4 Co1 125.4(2) . . ?
C4 N4 Co1 127.8(2) . . ?
C11 N5 C12 120.0(3) . . ?
C12 N6 C19 106.3(3) . . ?
C12 N6 Co1 126.1(2) . . ?
C19 N6 Co1 127.6(2) . . ?
C19 N7 C20 121.9(3) . . ?
C20 N8 N9 105.3(3) . . ?
C20 N8 Co1 130.2(2) . . ?
N9 N8 Co1 124.4(2) . . ?
C22 N9 N8 110.9(3) . . ?
C23 O1 Co1 123.3(2) . . ?
C24 O2 Co1 121.7(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.347(4) . ?
C1 C2 1.369(5) . ?
C2 C3 1.408(5) . ?
C3 N2 1.362(4) . ?
C3 N3 1.369(4) . ?
C4 N3 1.290(4) . ?
C4 N4 1.408(4) . ?
C4 C5 1.476(5) . ?
C5 C6 1.389(5) . ?
C5 C10 1.393(5) . ?
C6 C7 1.386(5) . ?
C7 C8 1.396(5) . ?
C8 C9 1.389(5) . ?
C9 C10 1.374(5) . ?
C10 C11 1.460(5) . ?
C11 N5 1.331(4) . ?
C11 N4 1.354(4) . ?
C12 N5 1.338(4) . ?
C12 N6 1.342(4) . ?
C12 C13 1.470(5) . ?
C13 C14 1.383(5) . ?
C13 C18 1.384(5) . ?
C14 C15 1.397(5) . ?
C15 C16 1.398(5) . ?
C16 C17 1.378(5) . ?
C17 C18 1.394(5) . ?
C18 C19 1.465(5) . ?
C19 N7 1.288(4) . ?
C19 N6 1.412(4) . ?
C20 N8 1.354(4) . ?
C20 N7 1.376(4) . ?
C20 C21 1.395(5) . ?
C21 C22 1.362(5) . ?
C22 N9 1.336(4) . ?
C23 O1 1.419(4) . ?
C24 O2 1.431(4) . ?
Co1 N4 1.935(3) . ?
Co1 N6 1.947(3) . ?
Co1 N8 1.956(3) . ?
Co1 N2 1.961(3) . ?
Co1 O1 2.296(3) . ?
Co1 O2 2.348(3) . ?
N1 N2 1.351(4) . ?
N8 N9 1.357(4) . ?
