#------------------------------------------------------------------------------
#$Date: 2025-04-03 08:32:21 +0300 (Thu, 03 Apr 2025) $
#$Revision: 298703 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/39/7233928.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_7233928
loop_
_publ_author_name
'Benjamin D. Lindner'
'Fabian Paulus'
'Anthony L. Appleton'
'Manuel Schaffroth'
'Jens U. Engelhart'
'Korwin M. Schelkle'
'Olena Tverskoy'
'Frank Rominger'
'Manuel Hamburger'
'Uwe H. F. Bunz'
_publ_section_title
;
 Electron-transporting phenazinothiadiazoles with engineered
 microstructure
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              9609
_journal_page_last               9612
_journal_paper_doi               10.1039/C4TC01992J
_journal_volume                  2
_journal_year                    2014
_chemical_formula_sum            'C18 H12 Cu N2 O2'
_chemical_formula_weight         351.83
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 102.317(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.6258(12)
_cell_length_b                   8.5953(10)
_cell_length_c                   15.2192(17)
_cell_measurement_temperature    293(2)
_cell_volume                     1358.0(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0658
_diffrn_reflns_av_sigmaI/netI    0.0520
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7026
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.96
_exptl_absorpt_coefficient_mu    1.620
_exptl_crystal_density_diffrn    1.721
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             716
_refine_diff_density_max         0.574
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.144
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2664
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.144
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0485
_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)+(0.0475P)²+0.8035P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1119
_refine_ls_wR_factor_ref         0.1152
_reflns_number_gt                2374
_reflns_number_total             2664
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1000003.cif
_cod_data_source_block           PCOD1000003
_cod_depositor_comments
;

2025-04-01
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C36 H24 Cu2 N4 O4'
_cod_original_formula_weight         703.67
_cod_original_formula_units_Z            2
_cod_database_code               7233928
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
Cu1 Cu 0.62317(4) 0.87915(5) 0.05070(3) 0.02941(17) Uani 1 1 d . . .
N1 N 0.7454(2) 0.9971(3) -0.00453(17) 0.0271(6) Uani 1 1 d . . .
N2 N 0.5117(2) 0.7390(3) 0.10334(17) 0.0277(6) Uani 1 1 d . . .
O1 O 0.7425(2) 0.9216(3) 0.16208(15) 0.0334(6) Uani 1 1 d . . .
O2 O 0.5053(2) 0.8345(3) -0.06175(16) 0.0370(6) Uani 1 1 d . . .
C1 C 0.8317(3) 1.0212(4) 0.1510(2) 0.0276(7) Uani 1 1 d . . .
C2 C 0.9226(3) 1.0866(4) 0.2194(2) 0.0357(8) Uani 1 1 d . . .
H2 H 0.9240 1.0603 0.2789 0.043 Uiso 1 1 calc R . .
C3 C 1.0124(3) 1.1922(4) 0.1995(3) 0.0393(9) Uani 1 1 d . . .
H3 H 1.0723 1.2352 0.2469 0.047 Uiso 1 1 calc R . .
C4 C 1.0165(3) 1.2350(5) 0.1150(3) 0.0403(9) Uani 1 1 d . . .
H4 H 1.0768 1.3074 0.1049 0.048 Uiso 1 1 calc R . .
C5 C 0.9282(3) 1.1688(4) 0.0416(2) 0.0325(8) Uani 1 1 d . . .
C6 C 0.9230(3) 1.1996(5) -0.0499(2) 0.0392(9) Uani 1 1 d . . .
H6 H 0.9813 1.2688 -0.0662 0.047 Uiso 1 1 calc R . .
C7 C 0.8335(4) 1.1289(4) -0.1148(3) 0.0386(9) Uani 1 1 d . . .
H7 H 0.8314 1.1473 -0.1753 0.046 Uiso 1 1 calc R . .
C8 C 0.7445(3) 1.0280(4) -0.0892(2) 0.0328(8) Uani 1 1 d . . .
H8 H 0.6825 0.9810 -0.1337 0.039 Uiso 1 1 calc R . .
C9 C 0.8371(3) 1.0642(4) 0.0607(2) 0.0271(7) Uani 1 1 d . . .
C10 C 0.4266(3) 0.7202(4) -0.0529(2) 0.0285(7) Uani 1 1 d . . .
C11 C 0.3434(3) 0.6477(4) -0.1223(2) 0.0346(8) Uani 1 1 d . . .
H11 H 0.3414 0.6784 -0.1812 0.042 Uiso 1 1 calc R . .
C12 C 0.2614(3) 0.5279(4) -0.1059(3) 0.0378(9) Uani 1 1 d . . .
H12 H 0.2062 0.4808 -0.1542 0.045 Uiso 1 1 calc R . .
C13 C 0.2610(3) 0.4794(4) -0.0211(2) 0.0357(8) Uani 1 1 d . . .
H13 H 0.2061 0.3996 -0.0121 0.043 Uiso 1 1 calc R . .
C14 C 0.3425(3) 0.5485(4) 0.0527(2) 0.0295(7) Uani 1 1 d . . .
C15 C 0.3492(3) 0.5115(4) 0.1442(2) 0.0345(8) Uani 1 1 d . . .
H15 H 0.2958 0.4348 0.1592 0.041 Uiso 1 1 calc R . .
C16 C 0.4336(3) 0.5876(4) 0.2107(2) 0.0348(8) Uani 1 1 d . . .
H16 H 0.4364 0.5652 0.2708 0.042 Uiso 1 1 calc R . .
C17 C 0.5155(3) 0.6993(4) 0.1867(2) 0.0331(8) Uani 1 1 d . . .
H17 H 0.5753 0.7475 0.2320 0.040 Uiso 1 1 calc R . .
C18 C 0.4264(3) 0.6669(4) 0.0362(2) 0.0265(7) 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
O1 Cu1 O2 179.11(11) . .
O1 Cu1 N1 84.72(10) . .
O2 Cu1 N1 94.95(10) . .
O1 Cu1 N2 95.60(10) . .
O2 Cu1 N2 84.64(10) . .
N1 Cu1 N2 173.32(11) . .
C8 N1 C9 119.0(3) . .
C8 N1 Cu1 130.8(2) . .
C9 N1 Cu1 109.9(2) . .
C17 N2 C18 119.2(3) . .
C17 N2 Cu1 131.1(2) . .
C18 N2 Cu1 109.5(2) . .
C1 O1 Cu1 111.6(2) . .
C10 O2 Cu1 111.3(2) . .
O1 C1 C2 125.2(3) . .
O1 C1 C9 117.9(3) . .
C2 C1 C9 117.0(3) . .
C1 C2 C3 120.1(3) . .
C1 C2 H2 120.0 . .
C3 C2 H2 120.0 . .
C4 C3 C2 123.2(3) . .
C4 C3 H3 118.4 . .
C2 C3 H3 118.4 . .
C3 C4 C5 119.6(3) . .
C3 C4 H4 120.2 . .
C5 C4 H4 120.2 . .
C9 C5 C6 116.4(3) . .
C9 C5 C4 117.7(3) . .
C6 C5 C4 125.8(3) . .
C7 C6 C5 120.6(3) . .
C7 C6 H6 119.7 . .
C5 C6 H6 119.7 . .
C6 C7 C8 119.0(3) . .
C6 C7 H7 120.5 . .
C8 C7 H7 120.5 . .
N1 C8 C7 122.3(3) . .
N1 C8 H8 118.9 . .
C7 C8 H8 118.9 . .
N1 C9 C5 122.7(3) . .
N1 C9 C1 114.9(3) . .
C5 C9 C1 122.4(3) . .
O2 C10 C11 125.4(3) . .
O2 C10 C18 117.7(3) . .
C11 C10 C18 116.9(3) . .
C10 C11 C12 121.2(3) . .
C10 C11 H11 119.4 . .
C12 C11 H11 119.4 . .
C13 C12 C11 121.5(3) . .
C13 C12 H12 119.3 . .
C11 C12 H12 119.3 . .
C12 C13 C14 120.4(3) . .
C12 C13 H13 119.8 . .
C14 C13 H13 119.8 . .
C13 C14 C18 118.1(3) . .
C13 C14 C15 126.0(3) . .
C18 C14 C15 115.9(3) . .
C16 C15 C14 120.5(3) . .
C16 C15 H15 119.7 . .
C14 C15 H15 119.7 . .
C15 C16 C17 118.9(3) . .
C15 C16 H16 120.6 . .
C17 C16 H16 120.6 . .
N2 C17 C16 122.8(3) . .
N2 C17 H17 118.6 . .
C16 C17 H17 118.6 . .
N2 C18 C14 122.7(3) . .
N2 C18 C10 115.5(3) . .
C14 C18 C10 121.9(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O1 1.922(2) .
Cu1 O2 1.932(2) .
Cu1 N1 1.972(3) .
Cu1 N2 1.975(3) .
N1 C8 1.314(4) .
N1 C9 1.362(4) .
N2 C17 1.306(4) .
N2 C18 1.362(4) .
O1 C1 1.315(4) .
O2 C10 1.315(4) .
C1 C2 1.380(5) .
C1 C9 1.435(5) .
C2 C3 1.397(5) .
C2 H2 0.9300 .
C3 C4 1.348(5) .
C3 H3 0.9300 .
C4 C5 1.415(5) .
C4 H4 0.9300 .
C5 C9 1.398(5) .
C5 C6 1.407(5) .
C6 C7 1.359(5) .
C6 H6 0.9300 .
C7 C8 1.398(5) .
C7 H7 0.9300 .
C8 H8 0.9300 .
C10 C11 1.374(5) .
C10 C18 1.432(5) .
C11 C12 1.405(5) .
C11 H11 0.9300 .
C12 C13 1.357(5) .
C12 H12 0.9300 .
C13 C14 1.396(5) .
C13 H13 0.9300 .
C14 C18 1.410(5) .
C14 C15 1.415(5) .
C15 C16 1.367(5) .
C15 H15 0.9300 .
C16 C17 1.396(5) .
C16 H16 0.9300 .
C17 H17 0.9300 .
