#------------------------------------------------------------------------------
#$Date: 2020-07-06 05:04:07 +0300 (Mon, 06 Jul 2020) $
#$Revision: 253820 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/65/7126589.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_7126589
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 N9 O2 Zn'
_chemical_formula_weight         532.87
_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                 102.434(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.8862(4)
_cell_length_b                   23.1744(14)
_cell_length_c                   14.2313(8)
_cell_measurement_reflns_used    7133
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.19
_cell_measurement_theta_min      3.02
_cell_volume                     2217.8(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 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0617
_diffrn_reflns_av_unetI/netI     0.0772
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            21335
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.344
_diffrn_reflns_theta_min         1.709
_exptl_absorpt_coefficient_mu    1.153
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6892
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.596
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.288
_exptl_crystal_size_mid          0.086
_exptl_crystal_size_min          0.060
_refine_diff_density_max         1.555
_refine_diff_density_min         -0.678
_refine_diff_density_rms         0.100
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         5523
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0910
_refine_ls_R_factor_gt           0.0511
_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)+(0.0495P)²+1.3705P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1083
_refine_ls_wR_factor_ref         0.1229
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3745
_reflns_number_total             5523
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc03060k2.cif
_cod_data_source_block           Zn(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               7126589
_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 0.9124(5) 0.30214(15) 0.6216(2) 0.0241(8) Uani 1 1 d . . . . .
H1 H 0.957133 0.279347 0.677596 0.029 Uiso 1 1 calc R U . . .
C2 C 1.0189(5) 0.34415(15) 0.5872(2) 0.0219(7) Uani 1 1 d . . . . .
H2 H 1.150965 0.356255 0.614250 0.026 Uiso 1 1 calc R U . . .
C3 C 0.8932(4) 0.36539(14) 0.5044(2) 0.0161(7) Uani 1 1 d . . . . .
C4 C 0.8201(4) 0.42838(14) 0.3696(2) 0.0146(6) Uani 1 1 d . . . . .
C5 C 0.8723(4) 0.47536(13) 0.3102(2) 0.0151(6) Uani 1 1 d . . . . .
C6 C 1.0415(5) 0.50873(14) 0.3185(2) 0.0190(7) Uani 1 1 d . . . . .
H6 H 1.155069 0.502502 0.368699 0.023 Uiso 1 1 calc R U . . .
C7 C 1.0380(5) 0.55184(15) 0.2501(2) 0.0231(7) Uani 1 1 d . . . . .
H7 H 1.152349 0.575356 0.253645 0.028 Uiso 1 1 calc R U . . .
C8 C 0.8718(5) 0.56148(15) 0.1768(2) 0.0220(7) Uani 1 1 d . . . . .
H8 H 0.873202 0.591835 0.132092 0.026 Uiso 1 1 calc R U . . .
C9 C 0.7028(5) 0.52692(14) 0.1684(2) 0.0203(7) Uani 1 1 d . . . . .
H9 H 0.589618 0.532450 0.117660 0.024 Uiso 1 1 calc R U . . .
C10 C 0.7068(4) 0.48436(13) 0.2367(2) 0.0141(6) Uani 1 1 d . . . . .
C11 C 0.5551(4) 0.44205(13) 0.2513(2) 0.0141(6) Uani 1 1 d . . . . .
C12 C 0.2347(4) 0.40332(13) 0.2026(2) 0.0136(6) Uani 1 1 d . . . . .
C13 C 0.0444(4) 0.40171(13) 0.1321(2) 0.0156(7) Uani 1 1 d . . . . .
C14 C -0.0165(5) 0.43021(14) 0.0465(2) 0.0191(7) Uani 1 1 d . . . . .
H14 H 0.068460 0.456653 0.023871 0.023 Uiso 1 1 calc R U . . .
C15 C -0.2075(5) 0.41896(15) -0.0060(2) 0.0211(7) Uani 1 1 d . . . . .
H15 H -0.254920 0.438345 -0.065318 0.025 Uiso 1 1 calc R U . . .
C16 C -0.3298(5) 0.37987(14) 0.0270(2) 0.0207(7) Uani 1 1 d . . . . .
H16 H -0.460106 0.373181 -0.009909 0.025 Uiso 1 1 calc R U . . .
C17 C -0.2654(5) 0.35023(14) 0.1130(2) 0.0182(7) Uani 1 1 d . . . . .
H17 H -0.349107 0.323337 0.135478 0.022 Uiso 1 1 calc R U . . .
C18 C -0.0747(4) 0.36141(13) 0.1647(2) 0.0144(6) Uani 1 1 d . . . . .
C19 C 0.0481(4) 0.33739(13) 0.2548(2) 0.0135(6) Uani 1 1 d . . . . .
C20 C 0.1083(5) 0.27063(13) 0.3860(2) 0.0163(7) Uani 1 1 d . . . . .
C21 C 0.0533(5) 0.22381(15) 0.4349(2) 0.0239(8) Uani 1 1 d . . . . .
H21 H -0.068615 0.203103 0.420640 0.029 Uiso 1 1 calc R U . . .
C22 C 0.2144(5) 0.21410(15) 0.5086(2) 0.0240(8) Uani 1 1 d . . . . .
H22 H 0.221511 0.184377 0.555161 0.029 Uiso 1 1 calc R U . . .
C23 C 0.5155(6) 0.22070(15) 0.2833(3) 0.0308(9) Uani 1 1 d . . . . .
H23A H 0.543122 0.203557 0.347715 0.046 Uiso 1 1 calc R U . . .
H23B H 0.587099 0.199219 0.242008 0.046 Uiso 1 1 calc R U . . .
H23C H 0.372315 0.219010 0.255772 0.046 Uiso 1 1 calc R U . . .
C24 C 0.4473(5) 0.43556(18) 0.5673(2) 0.0338(9) Uani 1 1 d . . . . .
H24A H 0.418269 0.407112 0.613373 0.051 Uiso 1 1 calc R U . . .
H24B H 0.397072 0.473433 0.581477 0.051 Uiso 1 1 calc R U . . .
H24C H 0.591379 0.437796 0.572607 0.051 Uiso 1 1 calc R U . . .
H25 H 0.232(6) 0.4183(16) 0.472(2) 0.027(11) Uiso 1 1 d . . . . .
H26 H 0.704(6) 0.2798(17) 0.295(3) 0.035(12) Uiso 1 1 d . . . . .
N1 N 0.7336(4) 0.29918(12) 0.56172(18) 0.0208(6) Uani 1 1 d . . . . .
H1A H 0.638428 0.275291 0.568819 0.025 Uiso 1 1 calc R U . . .
N2 N 0.7181(4) 0.33730(12) 0.48956(17) 0.0176(6) Uani 1 1 d . . . . .
N3 N 0.9414(4) 0.40936(11) 0.44637(17) 0.0162(6) Uani 1 1 d . . . . .
N4 N 0.6267(4) 0.40999(11) 0.33017(17) 0.0138(5) Uani 1 1 d . . . . .
N5 N 0.3789(4) 0.43988(11) 0.19098(17) 0.0153(6) Uani 1 1 d . . . . .
N6 N 0.2326(4) 0.36546(11) 0.27307(17) 0.0148(5) Uani 1 1 d . . . . .
N7 N -0.0096(4) 0.29606(11) 0.30426(17) 0.0154(6) Uani 1 1 d . . . . .
N8 N 0.2952(4) 0.28753(11) 0.42934(17) 0.0170(6) Uani 1 1 d . . . . .
N9 N 0.3612(4) 0.25211(12) 0.50639(18) 0.0226(6) Uani 1 1 d . . . . .
O1 O 0.5785(4) 0.27858(10) 0.28940(17) 0.0248(6) Uani 1 1 d . . . . .
O2 O 0.3537(4) 0.41873(11) 0.47277(16) 0.0224(5) Uani 1 1 d . . . . .
Zn1 Zn 0.46519(5) 0.34834(2) 0.38473(3) 0.01848(12) Uani 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 0.0033 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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 '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
_geom_angle_publ_flag
N1 C1 C2 107.3(3) . . ?
N1 C1 H1 126.3 . . ?
C2 C1 H1 126.3 . . ?
C1 C2 C3 105.7(3) . . ?
C1 C2 H2 127.2 . . ?
C3 C2 H2 127.2 . . ?
N2 C3 C2 109.5(3) . . ?
N2 C3 N3 125.4(3) . . ?
C2 C3 N3 125.1(3) . . ?
N3 C4 N4 128.2(3) . . ?
N3 C4 C5 122.8(3) . . ?
N4 C4 C5 109.0(2) . . ?
C6 C5 C10 121.4(3) . . ?
C6 C5 C4 132.2(3) . . ?
C10 C5 C4 106.4(3) . . ?
C5 C6 C7 117.0(3) . . ?
C5 C6 H6 121.5 . . ?
C7 C6 H6 121.5 . . ?
C8 C7 C6 121.8(3) . . ?
C8 C7 H7 119.1 . . ?
C6 C7 H7 119.1 . . ?
C7 C8 C9 120.5(3) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C10 C9 C8 117.3(3) . . ?
C10 C9 H9 121.3 . . ?
C8 C9 H9 121.3 . . ?
C9 C10 C5 121.8(3) . . ?
C9 C10 C11 131.6(3) . . ?
C5 C10 C11 106.6(3) . . ?
N5 C11 N4 129.6(3) . . ?
N5 C11 C10 120.6(3) . . ?
N4 C11 C10 109.9(2) . . ?
N6 C12 N5 129.4(3) . . ?
N6 C12 C13 110.2(3) . . ?
N5 C12 C13 120.4(3) . . ?
C14 C13 C18 122.2(3) . . ?
C14 C13 C12 130.8(3) . . ?
C18 C13 C12 107.0(3) . . ?
C13 C14 C15 117.4(3) . . ?
C13 C14 H14 121.3 . . ?
C15 C14 H14 121.3 . . ?
C16 C15 C14 120.9(3) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C15 C16 C17 121.3(3) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
C18 C17 C16 117.5(3) . . ?
C18 C17 H17 121.3 . . ?
C16 C17 H17 121.3 . . ?
C17 C18 C13 120.6(3) . . ?
C17 C18 C19 133.5(3) . . ?
C13 C18 C19 105.9(3) . . ?
N7 C19 N6 127.7(3) . . ?
N7 C19 C18 124.1(3) . . ?
N6 C19 C18 108.1(3) . . ?
N8 C20 C21 109.4(3) . . ?
N8 C20 N7 125.4(3) . . ?
C21 C20 N7 125.2(3) . . ?
C22 C21 C20 104.4(3) . . ?
C22 C21 H21 127.8 . . ?
C20 C21 H21 127.8 . . ?
N9 C22 C21 111.3(3) . . ?
N9 C22 H22 124.4 . . ?
C21 C22 H22 124.4 . . ?
O1 C23 H23A 109.5 . . ?
O1 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O1 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O2 C24 H24A 109.5 . . ?
O2 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O2 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C1 N1 N2 111.3(3) . . ?
C1 N1 H1A 124.3 . . ?
N2 N1 H1A 124.3 . . ?
N1 N2 C3 106.1(2) . . ?
N1 N2 Zn1 123.6(2) . . ?
C3 N2 Zn1 130.2(2) . . ?
C4 N3 C3 123.5(3) . . ?
C11 N4 C4 108.2(2) . . ?
C11 N4 Zn1 124.4(2) . . ?
C4 N4 Zn1 127.25(19) . . ?
C11 N5 C12 122.8(3) . . ?
C12 N6 C19 108.8(2) . . ?
C12 N6 Zn1 125.5(2) . . ?
C19 N6 Zn1 125.7(2) . . ?
C19 N7 C20 124.8(3) . . ?
C20 N8 N9 108.0(2) . . ?
C20 N8 Zn1 127.9(2) . . ?
N9 N8 Zn1 123.8(2) . . ?
C22 N9 N8 106.9(3) . . ?
C23 O1 Zn1 123.8(2) . . ?
C23 O1 H26 109(3) . . ?
Zn1 O1 H26 112(3) . . ?
C24 O2 Zn1 125.4(2) . . ?
C24 O2 H25 105(2) . . ?
Zn1 O2 H25 116(3) . . ?
N8 Zn1 N6 88.26(10) . . ?
N8 Zn1 N2 98.23(10) . . ?
N6 Zn1 N2 173.44(10) . . ?
N8 Zn1 N4 176.19(10) . . ?
N6 Zn1 N4 88.19(10) . . ?
N2 Zn1 N4 85.29(10) . . ?
N8 Zn1 O2 92.29(10) . . ?
N6 Zn1 O2 89.32(9) . . ?
N2 Zn1 O2 91.32(9) . . ?
N4 Zn1 O2 89.08(9) . . ?
N8 Zn1 O1 89.34(10) . . ?
N6 Zn1 O1 89.24(9) . . ?
N2 Zn1 O1 89.92(10) . . ?
N4 Zn1 O1 89.21(9) . . ?
O2 Zn1 O1 177.80(8) . . ?
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 1.340(4) . ?
C1 C2 1.371(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.394(4) . ?
C2 H2 0.9500 . ?
C3 N2 1.346(4) . ?
C3 N3 1.396(4) . ?
C4 N3 1.301(4) . ?
C4 N4 1.396(4) . ?
C4 C5 1.470(4) . ?
C5 C6 1.382(4) . ?
C5 C10 1.386(4) . ?
C6 C7 1.391(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.391(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.396(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.381(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.479(4) . ?
C11 N5 1.328(4) . ?
C11 N4 1.348(4) . ?
C12 N6 1.335(4) . ?
C12 N5 1.343(4) . ?
C12 C13 1.469(4) . ?
C13 C14 1.369(4) . ?
C13 C18 1.388(4) . ?
C14 C15 1.391(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.385(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.391(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.384(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.484(4) . ?
C19 N7 1.300(4) . ?
C19 N6 1.401(4) . ?
C20 N8 1.360(4) . ?
C20 C21 1.386(4) . ?
C20 N7 1.397(4) . ?
C21 C22 1.371(5) . ?
C21 H21 0.9500 . ?
C22 N9 1.346(4) . ?
C22 H22 0.9500 . ?
C23 O1 1.407(4) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 O2 1.416(4) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
N1 N2 1.341(3) . ?
N1 H1A 0.8800 . ?
N2 Zn1 2.051(2) . ?
N4 Zn1 2.062(3) . ?
N6 Zn1 2.037(2) . ?
N8 N9 1.367(3) . ?
N8 Zn1 2.020(3) . ?
O1 Zn1 2.349(2) . ?
O1 H26 0.85(4) . ?
O2 Zn1 2.288(2) . ?
O2 H25 0.84(4) . ?
