Biliazine: a ring open phthalocyanine analog with a meso hydrogen bond.
Schrage, Briana R.; Nemykin, Victor N.; Ziegler, Christopher J.; Chemical communications (Cambridge, England) 56 (2020) 6628–6631; doi:10.1039/d0cc03060k

data_7126588
_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            'C11 H9 N5'
_chemical_formula_weight         211.23
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/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                 99.080(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.6141(5)
_cell_length_b                   12.7038(5)
_cell_length_c                   13.4922(6)
_cell_measurement_reflns_used    3911
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.19
_cell_measurement_theta_min      5.20
_cell_volume                     1965.74(15)
_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 0.951
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_Laue_measured_fraction_full 0.951
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6403
_diffrn_reflns_point_group_measured_fraction_full 0.951
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        67.330
_diffrn_reflns_theta_max         67.330
_diffrn_reflns_theta_min         5.196
_exptl_absorpt_coefficient_mu    0.757
_exptl_absorpt_correction_T_max  0.7529
_exptl_absorpt_correction_T_min  0.6255
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.244
_exptl_crystal_size_mid          0.105
_exptl_crystal_size_min          0.046
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         1687
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0461
_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/[\s^2^(Fo^2^)+(0.0934P)^2^+0.8496P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1266
_refine_ls_wR_factor_ref         0.1336
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1462
_reflns_number_total             1687
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc03060k2.cif
_cod_data_source_block           1
_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      'C 2/c'
_cod_database_code               7126588
_shelx_shelxl_version_number     2016/6
_shelx_res_checksum              63978