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#$Date: 2025-08-22 01:24:23 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301857 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/75/7117533.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_7117533
loop_
_publ_author_name
'Anup Rana'
'Pradeepta K. Panda'
_publ_section_title
;
 Beta-Tetrachlorotetramethoxyporphycenes: positional effect of
 substituents on structure and photophysical properties
;
_journal_name_full               Chem.Commun.
_journal_page_first              12239
_journal_paper_doi               10.1039/C5cc03867G
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C12 H10 Cl2 N2 O4'
_chemical_formula_sum            'C12 H10 Cl2 N2 O4'
_chemical_formula_weight         317.12
_chemical_name_common            bipyrrole
_chemical_name_systematic
; 
 4,4'-dichloro-3,3'-dimethoxy-1H,1'H-[2,2'-bipyrrole]-5,5'-dialdehyde 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-04-28 deposited with the CCDC.
2015-06-11 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 97.600(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.4859(8)
_cell_length_b                   20.457(4)
_cell_length_c                   14.700(3)
_cell_measurement_reflns_used    2111
_cell_measurement_temperature    298(2)
_cell_volume                     1337.1(4)
_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-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0582
_diffrn_reflns_av_sigmaI/netI    0.0438
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13757
_diffrn_reflns_theta_full        26.04
_diffrn_reflns_theta_max         26.04
_diffrn_reflns_theta_min         1.72
_exptl_absorpt_coefficient_mu    0.499
_exptl_absorpt_correction_T_max  0.9383
_exptl_absorpt_correction_T_min  0.9201
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.575
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.512
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.507
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2644
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.507
_refine_ls_R_factor_all          0.1538
_refine_ls_R_factor_gt           0.1507
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0425P)²+6.1420P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2654
_refine_ls_wR_factor_ref         0.2669
_reflns_number_gt                2587
_reflns_number_total             2644
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc03867g2.cif
_cod_data_source_block           CMBPYDA
_cod_original_cell_volume        1337.2(4)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7117533
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl2 Cl 0.1610(6) 0.75993(10) 0.86608(16) 0.0621(7) Uani 1 1 d . . .
Cl1 Cl 0.8309(6) 1.11122(12) 0.60554(15) 0.0635(7) Uani 1 1 d . . .
N2 N 0.1536(13) 0.9483(3) 0.8815(4) 0.0343(14) Uani 1 1 d . . .
N1 N 0.5186(15) 1.0552(3) 0.8253(4) 0.0408(16) Uani 1 1 d . . .
O1 O 0.5155(11) 0.9679(3) 0.6190(3) 0.0447(14) Uani 1 1 d . . .
C9 C -0.1277(16) 0.8819(4) 0.9782(5) 0.0379(17) Uani 1 1 d . . .
H9 H -0.1922 0.8404 0.9925 0.045 Uiso 1 1 calc R . .
O4 O -0.2097(13) 0.9291(3) 1.0200(4) 0.0501(14) Uani 1 1 d . . .
O3 O 0.6702(17) 1.1852(3) 0.8853(4) 0.0690(19) Uani 1 1 d . . .
C4 C 0.4632(16) 0.9992(3) 0.7761(5) 0.0351(16) Uani 1 1 d . . .
C6 C 0.3494(16) 0.8757(4) 0.7952(5) 0.0388(17) Uani 1 1 d . . .
C5 C 0.3280(15) 0.9425(4) 0.8129(5) 0.0351(16) Uani 1 1 d . . .
O2 O 0.5242(12) 0.8485(3) 0.7361(4) 0.0484(14) Uani 1 1 d . . .
C3 C 0.5598(14) 1.0099(4) 0.6911(5) 0.0346(16) Uani 1 1 d . . .
C1 C 0.6504(18) 1.1016(4) 0.7763(5) 0.0438(18) Uani 1 1 d . . .
C7 C 0.1896(17) 0.8431(3) 0.8552(5) 0.0385(18) Uani 1 1 d . . .
C11 C 0.7811(19) 0.9453(5) 0.5862(7) 0.063(3) Uani 1 1 d . . .
H11A H 0.9056 0.9819 0.5755 0.094 Uiso 1 1 calc R . .
H11B H 0.7280 0.9217 0.5299 0.094 Uiso 1 1 calc R . .
H11C H 0.8889 0.9169 0.6310 0.094 Uiso 1 1 calc R . .
C8 C 0.0631(15) 0.8885(3) 0.9086(5) 0.0340(16) Uani 1 1 d . . .
C12 C 0.364(2) 0.8167(4) 0.6578(6) 0.059(2) Uani 1 1 d . . .
H12A H 0.2000 0.7920 0.6763 0.088 Uiso 1 1 calc R . .
H12B H 0.4974 0.7877 0.6313 0.088 Uiso 1 1 calc R . .
H12C H 0.2872 0.8488 0.6132 0.088 Uiso 1 1 calc R . .
C2 C 0.6829(15) 1.0720(4) 0.6937(5) 0.0397(18) Uani 1 1 d . . .
C10 C 0.726(2) 1.1644(4) 0.8126(6) 0.054(2) Uani 1 1 d . . .
H10 H 0.8288 1.1922 0.7773 0.065 Uiso 1 1 calc R . .
H2N H 0.126(13) 0.980(3) 0.919(4) 0.016(16) Uiso 1 1 d . . .
H1N H 0.450(14) 1.065(3) 0.871(5) 0.019(17) 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'
Cl Cl 0.1484 0.1585 '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
C5 N2 C8 111.1(6) . .
C4 N1 C1 111.4(6) . .
C3 O1 C11 115.4(6) . .
O4 C9 C8 122.3(7) . .
N1 C4 C3 106.7(6) . .
N1 C4 C5 122.2(6) . .
C3 C4 C5 131.1(7) . .
O2 C6 C7 127.0(7) . .
O2 C6 C5 125.3(7) . .
C7 C6 C5 107.4(7) . .
N2 C5 C6 106.5(6) . .
N2 C5 C4 121.2(6) . .
C6 C5 C4 132.2(7) . .
C6 O2 C12 115.3(6) . .
O1 C3 C2 128.2(6) . .
O1 C3 C4 124.7(7) . .
C2 C3 C4 106.9(6) . .
N1 C1 C2 105.1(7) . .
N1 C1 C10 122.0(7) . .
C2 C1 C10 133.0(8) . .
C6 C7 C8 109.0(6) . .
C6 C7 Cl2 126.2(6) . .
C8 C7 Cl2 124.9(6) . .
N2 C8 C7 106.0(6) . .
N2 C8 C9 121.6(6) . .
C7 C8 C9 132.3(7) . .
C1 C2 C3 109.8(7) . .
C1 C2 Cl1 123.4(6) . .
C3 C2 Cl1 126.6(6) . .
O3 C10 C1 125.8(8) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl2 C7 1.715(7) .
Cl1 C2 1.730(7) .
N2 C5 1.361(9) .
N2 C8 1.364(9) .
N1 C4 1.361(9) .
N1 C1 1.373(10) .
O1 C3 1.357(8) .
O1 C11 1.421(9) .
C9 O4 1.226(9) .
C9 C8 1.425(10) .
O3 C10 1.208(10) .
C4 C3 1.393(10) .
C4 C5 1.446(10) .
C6 O2 1.363(9) .
C6 C7 1.380(11) .
C6 C5 1.398(10) .
O2 C12 1.431(10) .
C3 C2 1.384(11) .
C1 C2 1.381(10) .
C1 C10 1.415(11) .
C7 C8 1.385(10) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 122379859
