#------------------------------------------------------------------------------
#$Date: 2020-07-06 05:04:07 +0300 (Mon, 06 Jul 2020) $
#$Revision: 253820 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/65/7126588.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_7126588
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            '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       'φ and ω 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/[σ²(Fo²)+(0.0934P)²+0.8496P] where P=(Fo²+2Fc²)/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 > 2σ(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_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, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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 0.76680(16) 0.85769(13) 0.07075(13) 0.0226(4) Uani 1 1 d . . . . .
H1 H 0.719414 0.901187 0.023598 0.027 Uiso 1 1 calc R U . . .
C2 C 0.72838(16) 0.81177(14) 0.15307(13) 0.0214(4) Uani 1 1 d . . . . .
H6 H 0.653535 0.817463 0.172593 0.026 Uiso 1 1 calc R U . . .
C3 C 0.82453(16) 0.75543(14) 0.20056(13) 0.0205(4) Uani 1 1 d . . . . .
C4 C 0.77270(15) 0.67100(13) 0.34068(12) 0.0181(4) Uani 1 1 d . . . . .
C5 C 0.79888(16) 0.62936(13) 0.44504(13) 0.0194(4) Uani 1 1 d . . . . .
C6 C 0.69198(15) 0.61578(13) 0.47692(12) 0.0191(4) Uani 1 1 d . . . . .
C7 C 0.68270(16) 0.57706(13) 0.57114(12) 0.0217(4) Uani 1 1 d . . . . .
H5 H 0.609177 0.569242 0.592743 0.026 Uiso 1 1 calc R U . . .
C8 C 0.78645(17) 0.55002(14) 0.63301(13) 0.0246(4) Uani 1 1 d . . . . .
H2 H 0.783604 0.521334 0.697605 0.030 Uiso 1 1 calc R U . . .
C9 C 0.60390(15) 0.64556(13) 0.38942(13) 0.0190(4) Uani 1 1 d . . . . .
C10 C 0.89356(16) 0.56428(14) 0.60185(13) 0.0252(5) Uani 1 1 d . . . . .
H3 H 0.962647 0.545717 0.645935 0.030 Uiso 1 1 calc R U . . .
C11 C 0.90248(16) 0.60532(13) 0.50711(13) 0.0221(4) Uani 1 1 d . . . . .
H4 H 0.975986 0.616206 0.486294 0.027 Uiso 1 1 calc R U . . .
N1 N 0.49084(13) 0.64267(11) 0.38802(11) 0.0213(4) Uani 1 1 d . . . . .
H1A H 0.443237 0.660593 0.333256 0.026 Uiso 1 1 calc R U . . .
H1B H 0.462530 0.622812 0.441838 0.026 Uiso 1 1 calc R U . . .
N2 N 0.65335(13) 0.67489(12) 0.31061(11) 0.0199(4) Uani 1 1 d . . . . .
N3 N 0.85311(13) 0.70120(11) 0.29102(11) 0.0199(4) Uani 1 1 d . . . . .
N4 N 0.91070(14) 0.77071(12) 0.14521(11) 0.0224(4) Uani 1 1 d . . . . .
N5 N 0.87724(14) 0.83409(12) 0.06514(11) 0.0237(4) Uani 1 1 d . . . . .
H7 H 0.992(2) 0.7460(19) 0.1592(17) 0.037(6) 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'
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
N5 C1 C2 112.64(16) . . ?
N5 C1 H1 123.7 . . ?
C2 C1 H1 123.7 . . ?
C1 C2 C3 104.36(17) . . ?
C1 C2 H6 127.8 . . ?
C3 C2 H6 127.8 . . ?
N4 C3 C2 106.32(16) . . ?
N4 C3 N3 117.31(15) . . ?
C2 C3 N3 135.91(18) . . ?
N3 C4 N2 127.68(15) . . ?
N3 C4 C5 122.66(15) . . ?
N2 C4 C5 109.62(15) . . ?
C6 C5 C11 121.25(17) . . ?
C6 C5 C4 106.14(14) . . ?
C11 C5 C4 132.61(18) . . ?
C7 C6 C5 122.18(16) . . ?
C7 C6 C9 132.68(17) . . ?
C5 C6 C9 105.06(15) . . ?
C6 C7 C8 116.87(17) . . ?
C6 C7 H5 121.6 . . ?
C8 C7 H5 121.6 . . ?
C10 C8 C7 121.17(17) . . ?
C10 C8 H2 119.4 . . ?
C7 C8 H2 119.4 . . ?
N1 C9 N2 123.42(15) . . ?
N1 C9 C6 124.58(16) . . ?
N2 C9 C6 111.99(15) . . ?
C8 C10 C11 121.67(16) . . ?
C8 C10 H3 119.2 . . ?
C11 C10 H3 119.2 . . ?
C5 C11 C10 116.83(17) . . ?
C5 C11 H4 121.6 . . ?
C10 C11 H4 121.6 . . ?
C9 N1 H1A 120.0 . . ?
C9 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C9 N2 C4 107.04(14) . . ?
C4 N3 C3 120.60(15) . . ?
C3 N4 N5 112.41(15) . . ?
C3 N4 H7 128.3(14) . . ?
N5 N4 H7 119.1(14) . . ?
C1 N5 N4 104.26(15) . . ?
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 N5 1.331(2) . ?
C1 C2 1.389(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.394(3) . ?
C2 H6 0.9500 . ?
C3 N4 1.354(3) . ?
C3 N3 1.395(2) . ?
C4 N3 1.291(2) . ?
C4 N2 1.382(2) . ?
C4 C5 1.490(2) . ?
C5 C6 1.387(3) . ?
C5 C11 1.387(2) . ?
C6 C7 1.383(2) . ?
C6 C9 1.484(2) . ?
C7 C8 1.396(3) . ?
C7 H5 0.9500 . ?
C8 C10 1.386(3) . ?
C8 H2 0.9500 . ?
C9 N1 1.311(2) . ?
C9 N2 1.339(2) . ?
C10 C11 1.399(3) . ?
C10 H3 0.9500 . ?
C11 H4 0.9500 . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
N4 N5 1.354(2) . ?
N4 H7 0.99(3) . ?
