#------------------------------------------------------------------------------
#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/24/7122492.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_7122492
loop_
_publ_author_name
'Kishore, M. V. Nanda'
'Panda, Pradeepta K.'
_publ_section_title
;
 Revisiting the intense NIR active bronzaphyrin, a 26-π aromatic expanded
 porphyrin: synthesis and structural analysis.
;
_journal_issue                   93
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              13135
_journal_page_last               13138
_journal_paper_doi               10.1039/c8cc07752e
_journal_volume                  54
_journal_year                    2018
_chemical_formula_moiety         'C24 H32 N2 O4'
_chemical_formula_sum            'C24 H32 N2 O4'
_chemical_formula_weight         412.51
_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'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_block_doi                 10.5517/ccdc.csd.cc1mcpf3
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-08-24 deposited with the CCDC.
2018-10-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.48(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.470(3)
_cell_length_b                   15.343(3)
_cell_length_c                   12.671(3)
_cell_measurement_reflns_used    4854
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.85
_cell_measurement_theta_min      2.65
_cell_volume                     2401.9(11)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9605
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.013
_diffrn_reflns_theta_min         2.116
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.141
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   0.994
_exptl_transmission_factor_min   0.989
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     143
_refine_ls_number_reflns         2375
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0740
_refine_ls_R_factor_gt           0.0618
_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)+(0.1087P)²+0.7651P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1724
_refine_ls_wR_factor_ref         0.1844
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1874
_reflns_number_total             2375
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8cc07752e2.cif
_cod_data_source_block           MA
_cod_depositor_comments
'Adding full bibliography for 7122492--7122493.cif.'
_cod_original_cell_volume        2401.9(10)
_cod_database_code               7122492
_shelx_shelxl_version_number     2014/7
_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
N1 N 0.16770(12) 0.37879(10) -0.02280(13) 0.0603(4) Uani 1 1 d . .
O1 O 0.35369(12) 0.37657(9) 0.27118(11) 0.0789(5) Uani 1 1 d . .
O2 O 0.30276(16) 0.26794(10) 0.14552(12) 0.0983(6) Uani 1 1 d . .
C1 C 0.10613(13) 0.44560(11) -0.08519(15) 0.0569(5) Uani 1 1 d . .
C2 C 0.03291(13) 0.43834(10) -0.20099(15) 0.0585(5) Uani 1 1 d . .
C3 C 0.20138(14) 0.49353(11) 0.09547(15) 0.0591(5) Uani 1 1 d . .
C4 C 0.22704(14) 0.40642(11) 0.08641(14) 0.0588(5) Uani 1 1 d . .
C5 C 0.12521(14) 0.51788(11) -0.01338(16) 0.0594(5) Uani 1 1 d . .
C6 C 0.29633(16) 0.34338(13) 0.16774(16) 0.0675(5) Uani 1 1 d . .
C7 C 0.24597(17) 0.55170(13) 0.19966(17) 0.0733(6) Uani 1 1 d . .
H7A H 0.1927 0.5959 0.1943 0.088 Uiso 1 1 calc R U
H7B H 0.2588 0.5173 0.2681 0.088 Uiso 1 1 calc R U
C8 C 0.07216(18) 0.60494(12) -0.05138(19) 0.0746(6) Uani 1 1 d . .
H8A H -0.0020 0.5960 -0.1054 0.090 Uiso 1 1 calc R U
H8B H 0.0704 0.6355 0.0149 0.090 Uiso 1 1 calc R U
C9 C 0.4209(2) 0.31670(17) 0.35833(18) 0.0991(8) Uani 1 1 d . .
H9A H 0.4653 0.2828 0.3291 0.119 Uiso 1 1 calc R U
H9B H 0.3761 0.2769 0.3796 0.119 Uiso 1 1 calc R U
C10 C 0.4897(3) 0.3673(2) 0.4586(2) 0.1368(13) Uani 1 1 d . .
H10A H 0.5340 0.4063 0.4369 0.205 Uiso 1 1 calc R U
H10B H 0.5351 0.3285 0.5175 0.205 Uiso 1 1 calc R U
H10C H 0.4451 0.4003 0.4872 0.205 Uiso 1 1 calc R U
C11 C 0.1290(2) 0.66058(17) -0.1069(2) 0.1066(9) Uani 1 1 d . .
H11A H 0.2004 0.6742 -0.0517 0.160 Uiso 1 1 calc R U
H11B H 0.0890 0.7135 -0.1342 0.160 Uiso 1 1 calc R U
H11C H 0.1340 0.6297 -0.1705 0.160 Uiso 1 1 calc R U
C12 C 0.3489(2) 0.5950(2) 0.2110(2) 0.1218(11) Uani 1 1 d . .
H12A H 0.4040 0.5517 0.2241 0.183 Uiso 1 1 calc R U
H12B H 0.3712 0.6349 0.2747 0.183 Uiso 1 1 calc R U
H12C H 0.3376 0.6263 0.1416 0.183 Uiso 1 1 calc R U
H1A H 0.1701(15) 0.3272(14) -0.0474(16) 0.065(5) 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 0.0033 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1002/ejoc.201700891 2017
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
C1 N1 C4 109.40(15) .
C6 O1 C9 116.82(17) .
N1 C1 C5 108.07(16) .
N1 C1 C2 123.98(15) .
C5 C1 C2 127.89(16) .
C2 C2 C1 174.89(14) 2_554
C4 C3 C5 106.38(15) .
C4 C3 C7 127.87(16) .
C5 C3 C7 125.75(16) .
N1 C4 C3 108.51(15) .
N1 C4 C6 117.77(16) .
C3 C4 C6 133.65(16) .
C1 C5 C3 107.63(15) .
C1 C5 C8 123.99(17) .
C3 C5 C8 128.38(17) .
O2 C6 O1 122.13(18) .
O2 C6 C4 124.17(18) .
O1 C6 C4 113.70(17) .
C12 C7 C3 112.3(2) .
C11 C8 C5 113.03(19) .
O1 C9 C10 108.3(2) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C1 1.357(2) .
N1 C4 1.361(2) .
O1 C6 1.329(2) .
O1 C9 1.445(3) .
O2 C6 1.203(2) .
C1 C5 1.392(2) .
C1 C2 1.409(3) .
C2 C2 1.205(3) 2_554
C3 C4 1.397(2) .
C3 C5 1.402(3) .
C3 C7 1.506(2) .
C4 C6 1.450(3) .
C5 C8 1.501(3) .
C7 C12 1.492(3) .
C8 C11 1.496(3) .
C9 C10 1.461(4) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139189234
