#------------------------------------------------------------------------------
#$Date: 2025-08-21 00:21:57 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301837 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/31/06/4310633.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_4310633
loop_
_publ_author_name
'Sara R. Halper'
'Mitchell R. Malachowski'
'Heather M. Delaney'
'Seth M. Cohen'
_publ_section_title
;
 Heteroleptic Copper Dipyrromethene Complexes: Synthesis, Structure, and
 Coordination Polymers
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              1242
_journal_page_last               1249
_journal_paper_doi               10.1021/ic0352295
_journal_volume                  43
_journal_year                    2004
_chemical_formula_sum            'C21 H17 Cu N3 O2'
_chemical_formula_weight         406.92
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.165(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.9543(10)
_cell_length_b                   20.6386(18)
_cell_length_c                   7.6606(7)
_cell_measurement_temperature    218(2)
_cell_volume                     1840.4(3)
_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      218(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_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  0.0285
_diffrn_reflns_av_sigmaI/netI    0.0207
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6593
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         1.97
_exptl_absorpt_coefficient_mu    1.208
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             836
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.433
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         2109
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0372
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0552P)²+1.3333P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0995
_refine_ls_wR_factor_ref         0.1010
_reflns_number_gt                1982
_reflns_number_total             2109
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic0352295si20031125_115511_6.cif
_cod_data_source_block           '[Cu(4-cydpm)(acac)]'
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_cell_volume        1840.3(3)
_cod_database_code               4310633
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5000 0.97130(13) 0.7500 0.0429(7) Uani 1 2 d S . .
C2 C 0.5000 0.90152(13) 0.7500 0.0354(5) Uani 1 2 d S . .
C3 C 0.52662(19) 0.86846(10) 0.9106(3) 0.0407(4) Uani 1 1 d . . .
H3 H 0.5449 0.8912 1.0198 0.049 Uiso 1 1 calc R . .
C4 C 0.52605(18) 0.80169(9) 0.9091(3) 0.0394(4) Uani 1 1 d . . .
H4 H 0.5437 0.7789 1.0182 0.047 Uiso 1 1 calc R . .
C5 C 0.5000 0.76774(12) 0.7500 0.0324(5) Uani 1 2 d S . .
C6 C 0.5000 0.69528(12) 0.7500 0.0309(5) Uani 1 2 d S . .
C7 C 0.40620(16) 0.66493(9) 0.7923(2) 0.0320(4) Uani 1 1 d . . .
C8 C 0.30745(17) 0.69424(10) 0.8305(3) 0.0375(4) Uani 1 1 d . . .
H8 H 0.2939 0.7389 0.8374 0.045 Uiso 1 1 calc R . .
C9 C 0.23567(18) 0.64549(10) 0.8554(3) 0.0423(5) Uani 1 1 d . . .
H9 H 0.1630 0.6500 0.8817 0.051 Uiso 1 1 calc R . .
C10 C 0.29162(17) 0.58736(10) 0.8340(3) 0.0384(4) Uani 1 1 d . . .
H10 H 0.2610 0.5460 0.8450 0.046 Uiso 1 1 calc R . .
C11 C 0.40899(18) 0.40627(9) 0.7965(3) 0.0372(4) Uani 1 1 d . . .
C12 C 0.3117(2) 0.36868(10) 0.8378(3) 0.0464(5) Uani 1 1 d . . .
H12A H 0.2970 0.3836 0.9506 0.070 Uiso 1 1 calc R . .
H12B H 0.3314 0.3230 0.8470 0.070 Uiso 1 1 calc R . .
H12C H 0.2436 0.3750 0.7428 0.070 Uiso 1 1 calc R . .
C13 C 0.5000 0.37526(13) 0.7500 0.0392(6) Uani 1 2 d S . .
H13 H 0.5000 0.3297 0.7500 0.047 Uiso 1 2 calc SR . .
Cu1 Cu 0.5000 0.532101(14) 0.7500 0.03700(14) Uani 1 2 d S . .
N1 N 0.39343(13) 0.59787(8) 0.7963(2) 0.0330(3) Uani 1 1 d . . .
N2 N 0.5000 1.02609(12) 0.7500 0.0570(8) Uani 1 2 d S . .
O1 O 0.40003(15) 0.46703(6) 0.8080(3) 0.0503(4) Uani 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'
Cu Cu 0.3201 1.2651 '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
N2 C1 C2 180.000(1) . . ?
C3 C2 C3 120.7(3) . 2_656 ?
C3 C2 C1 119.65(13) . . ?
C3 C2 C1 119.65(13) 2_656 . ?
C4 C3 C2 119.17(19) . . ?
C3 C4 C5 121.03(19) . . ?
C4 C5 C4 118.9(2) . 2_656 ?
C4 C5 C6 120.55(12) . . ?
C4 C5 C6 120.55(12) 2_656 . ?
C7 C6 C7 126.2(2) . 2_656 ?
C7 C6 C5 116.88(12) . . ?
C7 C6 C5 116.88(12) 2_656 . ?
C6 C7 N1 123.56(18) . . ?
C6 C7 C8 127.79(19) . . ?
N1 C7 C8 108.61(16) . . ?
C9 C8 C7 107.15(17) . . ?
C8 C9 C10 106.43(18) . . ?
N1 C10 C9 111.74(18) . . ?
O1 C11 C13 124.3(2) . . ?
O1 C11 C12 114.8(2) . . ?
C13 C11 C12 120.89(19) . . ?
C11 C13 C11 124.6(3) 2_656 . ?
O1 Cu1 O1 90.99(9) . 2_656 ?
O1 Cu1 N1 177.01(7) . 2_656 ?
O1 Cu1 N1 88.73(7) 2_656 2_656 ?
O1 Cu1 N1 88.73(7) . . ?
O1 Cu1 N1 177.01(7) 2_656 . ?
N1 Cu1 N1 91.70(9) 2_656 . ?
C10 N1 C7 106.07(16) . . ?
C10 N1 Cu1 126.45(14) . . ?
C7 N1 Cu1 127.47(13) . . ?
C11 O1 Cu1 127.76(16) . . ?
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 N2 1.131(4) . ?
C1 C2 1.440(4) . ?
C2 C3 1.379(2) . ?
C2 C3 1.379(2) 2_656 ?
C3 C4 1.378(3) . ?
C4 C5 1.379(2) . ?
C5 C4 1.379(2) 2_656 ?
C5 C6 1.495(3) . ?
C6 C7 1.386(2) . ?
C6 C7 1.386(2) 2_656 ?
C7 N1 1.394(2) . ?
C7 C8 1.415(3) . ?
C8 C9 1.364(3) . ?
C9 C10 1.401(3) . ?
C10 N1 1.331(3) . ?
C11 O1 1.263(2) . ?
C11 C13 1.377(3) . ?
C11 C12 1.490(3) . ?
C13 C11 1.377(3) 2_656 ?
Cu1 O1 1.9160(16) . ?
Cu1 O1 1.9160(16) 2_656 ?
Cu1 N1 1.9486(16) 2_656 ?
Cu1 N1 1.9486(16) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139130097
