#------------------------------------------------------------------------------
#$Date: 2020-07-06 05:04:07 +0300 (Mon, 06 Jul 2020) $
#$Revision: 253820 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/65/7126590.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_7126590
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            'C22 H15 N9'
_chemical_formula_weight         405.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_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                 93.02(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.579(6)
_cell_length_b                   17.112(13)
_cell_length_c                   23.460(16)
_cell_measurement_reflns_used    2923
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.18
_cell_measurement_theta_min      4.58
_cell_volume                     1836(3)
_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 0.941
_diffrn_measured_fraction_theta_max 0.941
_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  0.0668
_diffrn_reflns_av_unetI/netI     0.0815
_diffrn_reflns_Laue_measured_fraction_full 0.941
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            11216
_diffrn_reflns_point_group_measured_fraction_full 0.941
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_theta_full        67.428
_diffrn_reflns_theta_max         67.428
_diffrn_reflns_theta_min         3.198
_exptl_absorpt_coefficient_mu    0.772
_exptl_absorpt_correction_T_max  0.7530
_exptl_absorpt_correction_T_min  0.5655
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.415
_exptl_crystal_size_mid          0.153
_exptl_crystal_size_min          0.079
_refine_diff_density_max         0.367
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         3125
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.1127
_refine_ls_R_factor_gt           0.0674
_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)+(0.1101P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1725
_refine_ls_wR_factor_ref         0.1976
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1977
_reflns_number_total             3125
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc03060k2.cif
_cod_data_source_block           H2BlzH
_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/n'
_cod_database_code               7126590
_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+1/2, y+1/2, -z+1/2'
'-x, -y, -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
C1 C 1.1566(9) 0.5560(2) 0.57847(17) 0.0433(11) Uani 1 1 d . . . . .
H1 H 1.296599 0.516436 0.572028 0.052 Uiso 1 1 calc R U . . .
C2 C 0.9976(9) 0.5962(2) 0.53614(17) 0.0378(10) Uani 1 1 d . . . . .
H2 H 1.006328 0.589502 0.496058 0.045 Uiso 1 1 calc R U . . .
C3 C 0.8225(8) 0.6483(2) 0.56433(17) 0.0356(9) Uani 1 1 d . . . . .
C4 C 0.4744(8) 0.7485(2) 0.56690(16) 0.0323(9) Uani 1 1 d . . . . .
C5 C 0.2702(8) 0.8049(2) 0.53915(15) 0.0318(9) Uani 1 1 d . . . . .
C6 C 0.1954(8) 0.8208(2) 0.48234(16) 0.0343(9) Uani 1 1 d . . . . .
H6 H 0.286021 0.794234 0.452420 0.041 Uiso 1 1 calc R U . . .
C7 C -0.0175(9) 0.8773(2) 0.47100(17) 0.0371(10) Uani 1 1 d . . . . .
H7 H -0.075917 0.889210 0.432524 0.045 Uiso 1 1 calc R U . . .
C8 C -0.1467(9) 0.9167(2) 0.51491(16) 0.0384(10) Uani 1 1 d . . . . .
H8 H -0.291287 0.955127 0.505782 0.046 Uiso 1 1 calc R U . . .
C9 C -0.0699(9) 0.9012(2) 0.57166(16) 0.0362(9) Uani 1 1 d . . . . .
H9 H -0.158121 0.928413 0.601588 0.043 Uiso 1 1 calc R U . . .
C10 C 0.1402(9) 0.8447(2) 0.58290(16) 0.0342(9) Uani 1 1 d . . . . .
C11 C 0.2633(8) 0.8121(2) 0.63654(16) 0.0338(9) Uani 1 1 d . . . . .
C12 C 0.2557(8) 0.8071(2) 0.73626(16) 0.0341(9) Uani 1 1 d . . . . .
C13 C 0.1385(8) 0.8357(2) 0.79004(16) 0.0339(9) Uani 1 1 d . . . . .
C14 C -0.0611(9) 0.8948(2) 0.79982(16) 0.0367(9) Uani 1 1 d . . . . .
H14 H -0.144770 0.925702 0.769533 0.044 Uiso 1 1 calc R U . . .
C15 C -0.1321(9) 0.9064(2) 0.85574(16) 0.0375(10) Uani 1 1 d . . . . .
H15 H -0.267977 0.946227 0.864194 0.045 Uiso 1 1 calc R U . . .
C16 C -0.0074(9) 0.8606(2) 0.90024(17) 0.0385(10) Uani 1 1 d . . . . .
H16 H -0.061355 0.869690 0.938228 0.046 Uiso 1 1 calc R U . . .
C17 C 0.1921(9) 0.8027(2) 0.88986(16) 0.0367(9) Uani 1 1 d . . . . .
H17 H 0.279263 0.772263 0.920072 0.044 Uiso 1 1 calc R U . . .
C18 C 0.2610(8) 0.7904(2) 0.83368(16) 0.0328(9) Uani 1 1 d . . . . .
C19 C 0.4609(8) 0.7333(2) 0.80766(15) 0.0311(9) Uani 1 1 d . . . . .
C20 C 0.7954(8) 0.6293(2) 0.81065(17) 0.0352(9) Uani 1 1 d . . . . .
C21 C 0.9477(9) 0.5701(2) 0.83992(17) 0.0360(9) Uani 1 1 d . . . . .
H21 H 0.945736 0.557918 0.879407 0.043 Uiso 1 1 calc R U . . .
C22 C 1.1027(9) 0.5328(2) 0.79876(16) 0.0383(10) Uani 1 1 d . . . . .
H22 H 1.229851 0.489431 0.805109 0.046 Uiso 1 1 calc R U . . .
N1 N 1.0838(7) 0.58121(18) 0.62999(14) 0.0385(8) Uani 1 1 d . . . . .
N2 N 0.8791(8) 0.63773(18) 0.62122(15) 0.0403(9) Uani 1 1 d . . . . .
H2A H 0.795435 0.663717 0.648314 0.048 Uiso 1 1 calc R U . . .
N3 N 0.6339(7) 0.70118(18) 0.53868(13) 0.0349(8) Uani 1 1 d . . . . .
N4 N 0.4626(7) 0.75628(17) 0.62709(13) 0.0323(7) Uani 1 1 d . . . . .
N5 N 0.1695(7) 0.83878(18) 0.68648(13) 0.0355(8) Uani 1 1 d . . . . .
N6 N 0.4434(7) 0.74796(17) 0.74809(13) 0.0350(8) Uani 1 1 d . . . . .
H6A H 0.540550 0.722275 0.722674 0.042 Uiso 1 1 calc R U . . .
N7 N 0.6087(7) 0.68198(17) 0.83568(13) 0.0350(8) Uani 1 1 d . . . . .
N8 N 0.8514(7) 0.62732(18) 0.75457(14) 0.0374(8) Uani 1 1 d . . . . .
N9 N 1.0437(7) 0.56785(19) 0.74869(14) 0.0408(9) Uani 1 1 d . . . . .
H9A H 1.118907 0.554323 0.716378 0.049 Uiso 1 1 calc R U . . .
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'
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 109.9(3) . . ?
N1 C1 H1 125.0 . . ?
C2 C1 H1 125.0 . . ?
C1 C2 C3 105.8(4) . . ?
C1 C2 H2 127.1 . . ?
C3 C2 H2 127.1 . . ?
N2 C3 N3 127.1(3) . . ?
N2 C3 C2 107.3(4) . . ?
N3 C3 C2 125.6(4) . . ?
N3 C4 N4 128.2(4) . . ?
N3 C4 C5 123.1(3) . . ?
N4 C4 C5 108.7(3) . . ?
C6 C5 C10 121.3(4) . . ?
C6 C5 C4 132.3(3) . . ?
C10 C5 C4 106.3(3) . . ?
C5 C6 C7 117.2(3) . . ?
C5 C6 H6 121.4 . . ?
C7 C6 H6 121.4 . . ?
C6 C7 C8 121.2(4) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
C9 C8 C7 121.6(4) . . ?
C9 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
C10 C9 C8 117.2(3) . . ?
C10 C9 H9 121.4 . . ?
C8 C9 H9 121.4 . . ?
C9 C10 C5 121.5(4) . . ?
C9 C10 C11 131.7(3) . . ?
C5 C10 C11 106.7(4) . . ?
N4 C11 N5 129.2(4) . . ?
N4 C11 C10 111.3(3) . . ?
N5 C11 C10 119.5(3) . . ?
N5 C12 N6 130.1(3) . . ?
N5 C12 C13 120.7(3) . . ?
N6 C12 C13 109.2(3) . . ?
C18 C13 C14 122.1(3) . . ?
C18 C13 C12 107.2(3) . . ?
C14 C13 C12 130.7(4) . . ?
C15 C14 C13 116.8(4) . . ?
C15 C14 H14 121.6 . . ?
C13 C14 H14 121.6 . . ?
C14 C15 C16 121.2(4) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C17 C16 C15 121.2(3) . . ?
C17 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C16 C17 C18 117.6(4) . . ?
C16 C17 H17 121.2 . . ?
C18 C17 H17 121.2 . . ?
C13 C18 C17 121.1(3) . . ?
C13 C18 C19 107.4(3) . . ?
C17 C18 C19 131.6(4) . . ?
N7 C19 N6 129.2(3) . . ?
N7 C19 C18 124.2(3) . . ?
N6 C19 C18 106.5(3) . . ?
N8 C20 C21 110.2(3) . . ?
N8 C20 N7 125.3(4) . . ?
C21 C20 N7 124.5(4) . . ?
C22 C21 C20 104.7(4) . . ?
C22 C21 H21 127.7 . . ?
C20 C21 H21 127.7 . . ?
N9 C22 C21 108.6(4) . . ?
N9 C22 H22 125.7 . . ?
C21 C22 H22 125.7 . . ?
C1 N1 N2 107.2(3) . . ?
N1 N2 C3 109.8(3) . . ?
N1 N2 H2A 125.1 . . ?
C3 N2 H2A 125.1 . . ?
C4 N3 C3 123.2(4) . . ?
C11 N4 C4 106.9(3) . . ?
C12 N5 C11 122.2(3) . . ?
C12 N6 C19 109.7(3) . . ?
C12 N6 H6A 125.1 . . ?
C19 N6 H6A 125.1 . . ?
C19 N7 C20 123.4(3) . . ?
C20 N8 N9 105.9(3) . . ?
C22 N9 N8 110.5(3) . . ?
C22 N9 H9A 124.8 . . ?
N8 N9 H9A 124.8 . . ?
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 1.342(5) . ?
C1 C2 1.383(6) . ?
C1 H1 0.9500 . ?
C2 C3 1.390(5) . ?
C2 H2 0.9500 . ?
C3 N2 1.358(5) . ?
C3 N3 1.368(5) . ?
C4 N3 1.295(5) . ?
C4 N4 1.422(5) . ?
C4 C5 1.472(5) . ?
C5 C6 1.385(6) . ?
C5 C10 1.392(5) . ?
C6 C7 1.388(6) . ?
C6 H6 0.9500 . ?
C7 C8 1.389(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.384(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.379(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.462(6) . ?
C11 N4 1.348(5) . ?
C11 N5 1.348(5) . ?
C12 N5 1.328(5) . ?
C12 N6 1.347(5) . ?
C12 C13 1.480(5) . ?
C13 C18 1.380(6) . ?
C13 C14 1.390(5) . ?
C14 C15 1.382(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.403(6) . ?
C15 H15 0.9500 . ?
C16 C17 1.379(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.387(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.491(5) . ?
C19 N7 1.271(5) . ?
C19 N6 1.418(5) . ?
C20 N8 1.354(5) . ?
C20 C21 1.391(6) . ?
C20 N7 1.393(5) . ?
C21 C22 1.384(5) . ?
C21 H21 0.9500 . ?
C22 N9 1.334(5) . ?
C22 H22 0.9500 . ?
N1 N2 1.355(5) . ?
N2 H2A 0.8800 . ?
N6 H6A 0.8800 . ?
N8 N9 1.357(4) . ?
N9 H9A 0.8800 . ?
