#------------------------------------------------------------------------------
#$Date: 2019-11-17 15:31:42 +0200 (Sun, 17 Nov 2019) $
#$Revision: 230901 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/15/7231531.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_7231531
loop_
_publ_author_name
'Nikolaou, Vasilis'
'Plass, Fabian'
'Planchat, Aurélien'
'Charisiadis, Asterios'
'Charalambidis, Georgios'
'Angaridis, Panagiotis A.'
'Kahnt, Axel'
'Odobel, Fabrice'
'Coutsolelos, Athanassios G.'
_publ_section_title
;
 Effect of the triazole ring in zinc porphyrin-fullerene dyads on the
 charge transfer processes in NiO-based devices.
;
_journal_issue                   37
_journal_name_full               'Physical chemistry chemical physics : PCCP'
_journal_page_first              24477
_journal_page_last               24489
_journal_paper_doi               10.1039/c8cp04060e
_journal_volume                  20
_journal_year                    2018
_chemical_formula_sum            'C38 H34 N4'
_chemical_formula_weight         546.69
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-05-07 deposited with the CCDC.
2018-09-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.54(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.658(3)
_cell_length_b                   13.839(3)
_cell_length_c                   8.1732(16)
_cell_measurement_reflns_used    5662
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.242
_cell_measurement_theta_min      1.517
_cell_volume                     1518.8(6)
_computing_cell_refinement       'STOE X-Area'
_computing_data_collection       'STOE X-Area'
_computing_data_reduction        'STOE X-RED'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  STOE
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0
_diffrn_reflns_av_unetI/netI     0.0509
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_number            5662
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.274
_diffrn_reflns_theta_min         2.931
_exptl_absorpt_coefficient_mu    0.071
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             580
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.159
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3754
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.159
_refine_ls_R_factor_all          0.0946
_refine_ls_R_factor_gt           0.0571
_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)+(0.0560P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1309
_refine_ls_wR_factor_ref         0.1372
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2154
_reflns_number_total             3754
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8cp04060e2.cif
_cod_data_source_block           vn075
_cod_depositor_comments          'Adding full bibliography for 7231531.cif.'
_cod_original_cell_volume        1518.7(5)
_cod_database_code               7231531
_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+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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
N1 N 0.95355(10) 0.38772(11) 0.14091(18) 0.0420(4) Uani 1 1 d . .
H1A H 0.9715 0.4366 0.0885 0.050 Uiso 1 1 calc R U
N2 N 0.87307(10) 0.56997(11) 0.02575(18) 0.0420(4) Uani 1 1 d . .
C1 C 1.00728(13) 0.30399(13) 0.1738(2) 0.0435(4) Uani 1 1 d . .
C2 C 0.95039(14) 0.24169(14) 0.2587(2) 0.0502(5) Uani 1 1 d . .
H2A H 0.9680 0.1794 0.2952 0.060 Uiso 1 1 calc R U
C3 C 0.86578(14) 0.28898(15) 0.2772(2) 0.0507(5) Uani 1 1 d . .
H3A H 0.8158 0.2646 0.3289 0.061 Uiso 1 1 calc R U
C4 C 0.86698(12) 0.38263(14) 0.2035(2) 0.0436(4) Uani 1 1 d . .
C5 C 0.79568(12) 0.45581(14) 0.1958(2) 0.0431(4) Uani 1 1 d . .
C6 C 0.79835(12) 0.54292(13) 0.1092(2) 0.0421(4) Uani 1 1 d . .
C7 C 0.72192(13) 0.61750(15) 0.0922(3) 0.0516(5) Uani 1 1 d . .
H7A H 0.6643 0.6166 0.1378 0.062 Uiso 1 1 calc R U
C8 C 0.75061(14) 0.68779(15) -0.0020(3) 0.0540(5) Uani 1 1 d . .
H8A H 0.7163 0.7446 -0.0352 0.065 Uiso 1 1 calc R U
C9 C 0.84545(13) 0.65802(13) -0.0419(2) 0.0439(4) Uani 1 1 d . .
C10 C 0.90087(13) 0.71567(14) -0.1313(2) 0.0482(5) Uani 1 1 d . .
H10A H 0.8727 0.7749 -0.1670 0.058 Uiso 1 1 calc R U
C11 C 0.71141(13) 0.43598(14) 0.2865(2) 0.0451(4) Uani 1 1 d . .
C12 C 0.72688(14) 0.44740(15) 0.4608(2) 0.0518(5) Uani 1 1 d . .
C13 C 0.65117(17) 0.42163(16) 0.5445(3) 0.0604(6) Uani 1 1 d . .
H13A H 0.6621 0.4277 0.6598 0.072 Uiso 1 1 calc R U
C14 C 0.56016(16) 0.38727(16) 0.4633(3) 0.0597(5) Uani 1 1 d . .
C15 C 0.54507(14) 0.37988(15) 0.2911(3) 0.0576(5) Uani 1 1 d . .
H15A H 0.4833 0.3594 0.2342 0.069 Uiso 1 1 calc R U
C16 C 0.61922(13) 0.40206(14) 0.2003(2) 0.0499(5) Uani 1 1 d . .
C17 C 0.82366(17) 0.4885(2) 0.5566(3) 0.0751(7) Uani 1 1 d . .
H17A H 0.8679 0.5025 0.4809 0.113 Uiso 1 1 calc R U
H17B H 0.8101 0.5468 0.6120 0.113 Uiso 1 1 calc R U
H17C H 0.8542 0.4422 0.6376 0.113 Uiso 1 1 calc R U
C18 C 0.47873(19) 0.35889(19) 0.5578(4) 0.0840(8) Uani 1 1 d . .
H18A H 0.4214 0.3369 0.4807 0.126 Uiso 1 1 calc R U
H18B H 0.5024 0.3080 0.6347 0.126 Uiso 1 1 calc R U
H18C H 0.4609 0.4138 0.6177 0.126 Uiso 1 1 calc R U
C19 C 0.60111(16) 0.38884(19) 0.0142(3) 0.0706(7) Uani 1 1 d . .
H19A H 0.6596 0.4074 -0.0277 0.106 Uiso 1 1 calc R U
H19B H 0.5862 0.3223 -0.0123 0.106 Uiso 1 1 calc R U
H19C H 0.5460 0.4284 -0.0360 0.106 Uiso 1 1 calc R U
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'
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
C1 N1 C4 110.48(15) . .
C9 N2 C6 105.59(14) . .
N1 C1 C10 126.31(17) . 3_765
N1 C1 C2 106.67(15) . .
C10 C1 C2 127.01(17) 3_765 .
C3 C2 C1 108.28(17) . .
C2 C3 C4 108.27(16) . .
N1 C4 C5 125.87(17) . .
N1 C4 C3 106.28(15) . .
C5 C4 C3 127.85(17) . .
C4 C5 C6 124.29(16) . .
C4 C5 C11 115.79(16) . .
C6 C5 C11 119.92(16) . .
N2 C6 C5 124.97(15) . .
N2 C6 C7 110.04(16) . .
C5 C6 C7 124.98(17) . .
C8 C7 C6 106.80(17) . .
C7 C8 C9 106.81(17) . .
N2 C9 C10 126.00(16) . .
N2 C9 C8 110.75(16) . .
C10 C9 C8 123.19(17) . .
C1 C10 C9 128.36(17) 3_765 .
C16 C11 C12 119.92(17) . .
C16 C11 C5 120.63(17) . .
C12 C11 C5 119.39(16) . .
C13 C12 C11 118.83(18) . .
C13 C12 C17 119.91(19) . .
C11 C12 C17 121.25(18) . .
C14 C13 C12 122.5(2) . .
C13 C14 C15 117.77(18) . .
C13 C14 C18 121.6(2) . .
C15 C14 C18 120.7(2) . .
C14 C15 C16 122.39(19) . .
C15 C16 C11 118.51(18) . .
C15 C16 C19 120.62(18) . .
C11 C16 C19 120.87(17) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C1 1.372(2) .
N1 C4 1.373(2) .
N2 C9 1.363(2) .
N2 C6 1.379(2) .
C1 C10 1.388(2) 3_765
C1 C2 1.423(3) .
C2 C3 1.360(3) .
C3 C4 1.430(3) .
C4 C5 1.398(2) .
C5 C6 1.402(3) .
C5 C11 1.504(2) .
C6 C7 1.456(2) .
C7 C8 1.343(3) .
C8 C9 1.452(3) .
C9 C10 1.395(3) .
C10 C1 1.388(2) 3_765
C11 C16 1.406(3) .
C11 C12 1.410(3) .
C12 C13 1.387(3) .
C12 C17 1.518(3) .
C13 C14 1.382(3) .
C14 C15 1.389(3) .
C14 C18 1.517(3) .
C15 C16 1.395(3) .
C16 C19 1.507(3) .
