#------------------------------------------------------------------------------
#$Date: 2019-03-05 10:52:05 +0200 (Tue, 05 Mar 2019) $
#$Revision: 213973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/01/33/7013352.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_7013352
loop_
_publ_author_name
'Marilyn M. Olmstead'
'Ana de Bettencourt-Dias'
'Hon Man Lee'
'David Pham'
'Alan L. Balch'
_publ_section_title
;
 Interactions of metalloporphyrins as donors with the electron
 acceptors C60, tetracyanoquinomethane (TCNQ) and
 trinitrofluorenylidenemalonitrile
;
_journal_issue                   16
_journal_name_full               'Dalton Trans.'
_journal_page_first              3227
_journal_page_last               3232
_journal_paper_doi               10.1039/b306714a
_journal_year                    2003
_chemical_formula_sum            'C48 H48 Cu N8'
_chemical_formula_weight         800.48
_chemical_name_common            TCNQ$.!Cu(OEP)
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 94.018(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.0673(6)
_cell_length_b                   25.567(2)
_cell_length_c                   11.0938(9)
_cell_measurement_reflns_used    6327
_cell_measurement_temperature    89(2)
_cell_measurement_theta_max      31.5
_cell_measurement_theta_min      3.0
_cell_volume                     1999.6(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'SHELXTL 5.03, XP (Sheldrick, 1994)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      89(2)
_diffrn_measured_fraction_theta_full 0.958
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_device_type  'Bruker Smart 1000'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_sigmaI/netI    0.0200
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            27755
_diffrn_reflns_theta_full        31.50
_diffrn_reflns_theta_max         31.50
_diffrn_reflns_theta_min         2.01
_diffrn_standards_decay_%        <0.1
_diffrn_standards_number         '50 frames remeasured'
_exptl_absorpt_coefficient_mu    0.592
_exptl_absorpt_correction_T_max  0.9164
_exptl_absorpt_correction_T_min  0.7290
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2.0'
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             842
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.522
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         6376
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0325
_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)+(0.0523P)²+0.6200P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0873
_refine_ls_wR_factor_ref         0.0912
_reflns_number_gt                5514
_reflns_number_total             6376
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b306714a.txt
_cod_data_source_block           ab011
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7013352
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
Cu1 Cu 0.5000 0.0000 0.5000 0.01114(6) Uani 1 2 d S . .
N1 N 0.56122(13) 0.06699(3) 0.58755(8) 0.01296(17) Uani 1 1 d . . .
N2 N 0.39552(13) 0.03965(3) 0.35416(8) 0.01287(17) Uani 1 1 d . . .
N3 N -0.04579(18) 0.18174(5) 0.42378(12) 0.0305(3) Uani 1 1 d . . .
N4 N -0.24400(16) 0.07326(5) 0.13495(11) 0.0272(2) Uani 1 1 d . . .
C1 C 0.64646(15) 0.07347(4) 0.70217(10) 0.01408(19) Uani 1 1 d . . .
C2 C 0.66576(16) 0.12866(4) 0.73127(10) 0.0155(2) Uani 1 1 d . . .
C3 C 0.58986(16) 0.15536(4) 0.63297(10) 0.0155(2) Uani 1 1 d . . .
C4 C 0.52589(15) 0.11664(4) 0.54457(10) 0.01375(19) Uani 1 1 d . . .
C5 C 0.44446(15) 0.12879(4) 0.43049(10) 0.01462(19) Uani 1 1 d . . .
H5 H 0.4273 0.1648 0.4117 0.018 Uiso 1 1 calc R . .
C6 C 0.38603(15) 0.09314(4) 0.34178(10) 0.01340(19) Uani 1 1 d . . .
C7 C 0.30500(15) 0.10746(4) 0.22313(10) 0.01454(19) Uani 1 1 d . . .
C8 C 0.26490(15) 0.06168(4) 0.16282(10) 0.01473(19) Uani 1 1 d . . .
C9 C 0.32012(15) 0.01981(4) 0.24579(10) 0.01348(18) Uani 1 1 d . . .
C10 C 0.29819(15) -0.03317(4) 0.22005(10) 0.01471(19) Uani 1 1 d . . .
H10 H 0.2407 -0.0424 0.1430 0.018 Uiso 1 1 calc R . .
C11 C 0.76055(19) 0.15168(5) 0.84454(11) 0.0208(2) Uani 1 1 d . . .
H11A H 0.7569 0.1260 0.9111 0.025 Uiso 1 1 calc R . .
H11B H 0.6900 0.1832 0.8675 0.025 Uiso 1 1 calc R . .
C12 C 0.9673(2) 0.16659(6) 0.82772(13) 0.0287(3) Uani 1 1 d . . .
H12A H 1.0391 0.1352 0.8092 0.043 Uiso 1 1 calc R . .
H12B H 1.0234 0.1825 0.9022 0.043 Uiso 1 1 calc R . .
H12C H 0.9714 0.1916 0.7610 0.043 Uiso 1 1 calc R . .
C13 C 0.57214(17) 0.21347(4) 0.61686(11) 0.0187(2) Uani 1 1 d . . .
H13A H 0.6055 0.2227 0.5343 0.022 Uiso 1 1 calc R . .
H13B H 0.6644 0.2309 0.6749 0.022 Uiso 1 1 calc R . .
C14 C 0.3733(2) 0.23425(5) 0.63570(15) 0.0290(3) Uani 1 1 d . . .
H14A H 0.2809 0.2170 0.5789 0.044 Uiso 1 1 calc R . .
H14B H 0.3699 0.2721 0.6216 0.044 Uiso 1 1 calc R . .
H14C H 0.3418 0.2269 0.7187 0.044 Uiso 1 1 calc R . .
C15 C 0.28003(16) 0.16236(4) 0.17737(11) 0.0174(2) Uani 1 1 d . . .
H15A H 0.2250 0.1839 0.2403 0.021 Uiso 1 1 calc R . .
H15B H 0.1890 0.1622 0.1054 0.021 Uiso 1 1 calc R . .
C16 C 0.46680(18) 0.18752(5) 0.14362(12) 0.0221(2) Uani 1 1 d . . .
H16A H 0.5532 0.1910 0.2162 0.033 Uiso 1 1 calc R . .
H16B H 0.4406 0.2222 0.1087 0.033 Uiso 1 1 calc R . .
H16C H 0.5256 0.1654 0.0844 0.033 Uiso 1 1 calc R . .
C17 C 0.18696(17) 0.05551(5) 0.03418(10) 0.0184(2) Uani 1 1 d . . .
H17A H 0.0796 0.0800 0.0185 0.022 Uiso 1 1 calc R . .
H17B H 0.1375 0.0195 0.0223 0.022 Uiso 1 1 calc R . .
C18 C 0.33495(19) 0.06591(6) -0.05635(12) 0.0278(3) Uani 1 1 d . . .
H18A H 0.3816 0.1019 -0.0467 0.042 Uiso 1 1 calc R . .
H18B H 0.2775 0.0611 -0.1386 0.042 Uiso 1 1 calc R . .
H18C H 0.4409 0.0415 -0.0420 0.042 Uiso 1 1 calc R . .
C19 C 0.08527(17) 0.00895(5) 0.61650(11) 0.0185(2) Uani 1 1 d . . .
H19 H 0.1436 0.0143 0.6953 0.022 Uiso 1 1 calc R . .
C20 C 0.03569(17) 0.05075(5) 0.54712(11) 0.0187(2) Uani 1 1 d . . .
H20 H 0.0583 0.0850 0.5779 0.022 Uiso 1 1 calc R . .
C21 C -0.05149(16) 0.04387(5) 0.42645(10) 0.0170(2) Uani 1 1 d . . .
C22 C -0.10044(16) 0.08625(5) 0.35385(11) 0.0191(2) Uani 1 1 d . . .
C23 C -0.07015(18) 0.13916(5) 0.39346(12) 0.0225(2) Uani 1 1 d . . .
C24 C -0.18197(17) 0.07936(5) 0.23229(11) 0.0215(2) 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'
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
N1 Cu1 N1 180.00(3) . 3_656 ?
N1 Cu1 N2 89.21(4) . 3_656 ?
N1 Cu1 N2 90.79(4) 3_656 3_656 ?
N1 Cu1 N2 90.79(4) . . ?
N1 Cu1 N2 89.21(4) 3_656 . ?
N2 Cu1 N2 180.0 3_656 . ?
C4 N1 C1 105.45(9) . . ?
C4 N1 Cu1 126.51(7) . . ?
C1 N1 Cu1 128.04(7) . . ?
C6 N2 C9 105.41(9) . . ?
C6 N2 Cu1 126.56(7) . . ?
C9 N2 Cu1 128.02(7) . . ?
N1 C1 C10 124.91(10) . 3_656 ?
N1 C1 C2 110.50(9) . . ?
C10 C1 C2 124.57(10) 3_656 . ?
C3 C2 C1 106.44(9) . . ?
C3 C2 C11 126.86(10) . . ?
C1 C2 C11 126.61(10) . . ?
C2 C3 C4 106.66(9) . . ?
C2 C3 C13 127.99(10) . . ?
C4 C3 C13 125.35(10) . . ?
N1 C4 C5 125.26(10) . . ?
N1 C4 C3 110.95(10) . . ?
C5 C4 C3 123.77(10) . . ?
C6 C5 C4 125.83(10) . . ?
N2 C6 C5 125.02(10) . . ?
N2 C6 C7 110.86(9) . . ?
C5 C6 C7 124.11(10) . . ?
C8 C7 C6 106.50(9) . . ?
C8 C7 C15 128.33(10) . . ?
C6 C7 C15 125.12(10) . . ?
C7 C8 C9 106.52(9) . . ?
C7 C8 C17 127.17(10) . . ?
C9 C8 C17 126.26(10) . . ?
N2 C9 C10 124.66(10) . . ?
N2 C9 C8 110.69(9) . . ?
C10 C9 C8 124.65(10) . . ?
C1 C10 C9 125.11(10) 3_656 . ?
C2 C11 C12 111.62(10) . . ?
C3 C13 C14 113.41(10) . . ?
C7 C15 C16 113.04(9) . . ?
C8 C17 C18 112.65(10) . . ?
C20 C19 C21 121.43(11) . 3_556 ?
C19 C20 C21 120.61(11) . . ?
C22 C21 C20 121.23(11) . . ?
C22 C21 C19 120.81(11) . 3_556 ?
C20 C21 C19 117.96(10) . 3_556 ?
C21 C22 C23 122.42(11) . . ?
C21 C22 C24 121.21(12) . . ?
C23 C22 C24 116.35(11) . . ?
N3 C23 C22 179.18(14) . . ?
N4 C24 C22 178.67(14) . . ?
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
Cu1 N1 2.0013(9) . ?
Cu1 N1 2.0013(9) 3_656 ?
Cu1 N2 2.0058(9) 3_656 ?
Cu1 N2 2.0058(9) . ?
N1 C4 1.3725(13) . ?
N1 C1 1.3784(14) . ?
N2 C6 1.3757(13) . ?
N2 C9 1.3773(14) . ?
N3 C23 1.1489(18) . ?
N4 C24 1.1473(17) . ?
C1 C10 1.3827(15) 3_656 ?
C1 C2 1.4516(15) . ?
C2 C3 1.3643(16) . ?
C2 C11 1.5022(16) . ?
C3 C4 1.4436(15) . ?
C3 C13 1.5006(15) . ?
C4 C5 1.3883(15) . ?
C5 C6 1.3829(15) . ?
C6 C7 1.4452(15) . ?
C7 C8 1.3680(15) . ?
C7 C15 1.4989(15) . ?
C8 C9 1.4473(15) . ?
C8 C17 1.5016(15) . ?
C9 C10 1.3907(15) . ?
C10 C1 1.3827(15) 3_656 ?
C11 C12 1.5339(19) . ?
C13 C14 1.5304(18) . ?
C15 C16 1.5381(17) . ?
C17 C18 1.5233(17) . ?
C19 C20 1.3488(17) . ?
C19 C21 1.4463(16) 3_556 ?
C20 C21 1.4447(16) . ?
C21 C22 1.3797(17) . ?
C21 C19 1.4463(16) 3_556 ?
C22 C23 1.4337(18) . ?
C22 C24 1.4396(17) . ?
