#------------------------------------------------------------------------------
#$Date: 2019-03-05 10:52:05 +0200 (Tue, 05 Mar 2019) $
#$Revision: 213973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/01/33/7013355.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_7013355
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            'C84 H92 N12 Zn2'
_chemical_formula_weight         1400.44
_chemical_name_common            2{Zn(OEP)}.TCNQ
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 90.31(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.241(8)
_cell_length_b                   14.168(7)
_cell_length_c                   21.651(12)
_cell_measurement_reflns_used    996
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      20
_cell_measurement_theta_min      2.35
_cell_volume                     3448(4)
_computing_cell_refinement       'SAINT 6.22 (Bruker, 2002)'
_computing_data_collection       'SMART 5.054 (Bruker, 2002)'
_computing_data_reduction        'SAINT 6.22 (Bruker, 2002)'
_computing_molecular_graphics    'SHELXTL 5.1, XP (Sheldrick, 1994)'
_computing_publication_material  'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      90(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_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  0.097
_diffrn_reflns_av_sigmaI/netI    0.0298
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            44485
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         0.94
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.753
_exptl_absorpt_correction_T_max  0.9251
_exptl_absorpt_correction_T_min  0.6542
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2.03 (Sheldrick, 2002)'
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             1480
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.460
_refine_diff_density_min         -0.719
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.138
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     451
_refine_ls_number_reflns         8404
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.138
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0324
_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)+(0.0451P)²+1.8093P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0832
_refine_ls_wR_factor_ref         0.0905
_reflns_number_gt                7871
_reflns_number_total             8404
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b306714a.txt
_cod_data_source_block           dp07
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7013355
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
Zn1 Zn 0.30604(2) 0.455031(15) 0.492239(12) 0.01032(6) Uani 1 1 d . . .
N1 N 0.21456(15) 0.33093(11) 0.49261(8) 0.0103(3) Uani 1 1 d . . .
N2 N 0.33256(17) 0.44372(12) 0.58469(8) 0.0107(4) Uani 1 1 d . . .
N3 N 0.38609(16) 0.58412(11) 0.49302(9) 0.0109(3) Uani 1 1 d . . .
N4 N 0.26270(17) 0.47319(12) 0.40141(9) 0.0105(4) Uani 1 1 d . . .
C1 C 0.1995(2) 0.27166(14) 0.54198(9) 0.0111(4) Uani 1 1 d . . .
C2 C 0.1409(2) 0.18588(15) 0.52252(10) 0.0122(4) Uani 1 1 d . . .
C3 C 0.1179(2) 0.19534(15) 0.46073(10) 0.0117(4) Uani 1 1 d . . .
C4 C 0.1639(2) 0.28662(15) 0.44265(10) 0.0117(4) Uani 1 1 d . . .
C5 C 0.15556(19) 0.32584(15) 0.38372(10) 0.0116(4) Uani 1 1 d . . .
H5A H 0.1150 0.2894 0.3534 0.014 Uiso 1 1 calc R . .
C6 C 0.2000(2) 0.41240(14) 0.36458(9) 0.0111(4) Uani 1 1 d . . .
C7 C 0.1885(2) 0.45016(15) 0.30265(9) 0.0131(4) Uani 1 1 d . . .
C8 C 0.2488(2) 0.53326(16) 0.30208(10) 0.0131(4) Uani 1 1 d . . .
C9 C 0.2934(2) 0.54792(14) 0.36459(9) 0.0117(4) Uani 1 1 d . . .
C10 C 0.3567(2) 0.62663(15) 0.38465(10) 0.0116(4) Uani 1 1 d . . .
H10A H 0.3729 0.6734 0.3544 0.014 Uiso 1 1 calc R . .
C11 C 0.3989(2) 0.64450(15) 0.44407(10) 0.0111(4) Uani 1 1 d . . .
C12 C 0.46266(19) 0.72790(16) 0.46337(10) 0.0114(4) Uani 1 1 d . . .
C13 C 0.4894(2) 0.71711(15) 0.52470(10) 0.0108(4) Uani 1 1 d . . .
C14 C 0.4398(2) 0.62634(15) 0.54239(10) 0.0115(4) Uani 1 1 d . . .
C15 C 0.4431(2) 0.59010(15) 0.60209(10) 0.0120(4) Uani 1 1 d . . .
H15A H 0.4860 0.6255 0.6321 0.014 Uiso 1 1 calc R . .
C16 C 0.3898(2) 0.50694(15) 0.62215(9) 0.0105(4) Uani 1 1 d . . .
C17 C 0.3854(2) 0.47649(16) 0.68607(10) 0.0132(4) Uani 1 1 d . . .
C18 C 0.3241(2) 0.39388(14) 0.68659(9) 0.0129(4) Uani 1 1 d . . .
C19 C 0.2929(2) 0.37343(14) 0.62271(9) 0.0109(4) Uani 1 1 d . . .
C20 C 0.23286(19) 0.29308(15) 0.60263(10) 0.0124(4) Uani 1 1 d . . .
H20A H 0.2125 0.2481 0.6334 0.015 Uiso 1 1 calc R . .
C21 C 0.1124(2) 0.10293(15) 0.56303(10) 0.0144(4) Uani 1 1 d . . .
H21A H 0.0501 0.0645 0.5426 0.017 Uiso 1 1 calc R . .
H21B H 0.0795 0.1264 0.6025 0.017 Uiso 1 1 calc R . .
C22 C 0.2194(2) 0.03996(16) 0.57710(11) 0.0185(5) Uani 1 1 d . . .
H22A H 0.1930 -0.0160 0.5998 0.028 Uiso 1 1 calc R . .
H22B H 0.2772 0.0750 0.6022 0.028 Uiso 1 1 calc R . .
H22C H 0.2566 0.0205 0.5383 0.028 Uiso 1 1 calc R . .
C23 C 0.0616(2) 0.12459(16) 0.41818(11) 0.0153(4) Uani 1 1 d . . .
H23A H 0.0288 0.1579 0.3817 0.018 Uiso 1 1 calc R . .
H23B H -0.0055 0.0937 0.4397 0.018 Uiso 1 1 calc R . .
C24 C 0.1486(3) 0.04913(18) 0.39656(13) 0.0234(5) Uani 1 1 d . . .
H24A H 0.1089 0.0074 0.3668 0.035 Uiso 1 1 calc R . .
H24B H 0.1760 0.0121 0.4321 0.035 Uiso 1 1 calc R . .
H24C H 0.2170 0.0794 0.3768 0.035 Uiso 1 1 calc R . .
C25 C 0.1180(2) 0.40586(16) 0.25111(10) 0.0159(4) Uani 1 1 d . . .
H25A H 0.1366 0.3376 0.2494 0.019 Uiso 1 1 calc R . .
H25B H 0.1426 0.4344 0.2114 0.019 Uiso 1 1 calc R . .
C26 C -0.0153(2) 0.41826(19) 0.25859(12) 0.0210(5) Uani 1 1 d . . .
H26A H -0.0567 0.3889 0.2236 0.031 Uiso 1 1 calc R . .
H26B H -0.0345 0.4857 0.2599 0.031 Uiso 1 1 calc R . .
H26C H -0.0407 0.3882 0.2971 0.031 Uiso 1 1 calc R . .
C27 C 0.2682(2) 0.59746(17) 0.24759(10) 0.0186(5) Uani 1 1 d . . .
H27A H 0.2938 0.5588 0.2120 0.022 Uiso 1 1 calc R . .
H27B H 0.3338 0.6416 0.2577 0.022 Uiso 1 1 calc R . .
C28 C 0.1598(3) 0.6544(2) 0.22865(12) 0.0294(6) Uani 1 1 d . . .
H28A H 0.1794 0.6940 0.1930 0.044 Uiso 1 1 calc R . .
H28B H 0.1351 0.6945 0.2631 0.044 Uiso 1 1 calc R . .
H28C H 0.0948 0.6114 0.2176 0.044 Uiso 1 1 calc R . .
C29 C 0.4887(2) 0.81216(16) 0.42398(10) 0.0135(4) Uani 1 1 d . . .
H29A H 0.5010 0.7912 0.3809 0.016 Uiso 1 1 calc R . .
H29B H 0.5633 0.8420 0.4386 0.016 Uiso 1 1 calc R . .
C30 C 0.3884(3) 0.88534(18) 0.42529(12) 0.0249(5) Uani 1 1 d . . .
H30A H 0.4104 0.9397 0.3999 0.037 Uiso 1 1 calc R . .
H30B H 0.3754 0.9060 0.4679 0.037 Uiso 1 1 calc R . .
H30C H 0.3151 0.8571 0.4089 0.037 Uiso 1 1 calc R . .
C31 C 0.5529(2) 0.78361(15) 0.56700(10) 0.0136(4) Uani 1 1 d . . .
H31A H 0.6046 0.8252 0.5420 0.016 Uiso 1 1 calc R . .
H31B H 0.6048 0.7467 0.5950 0.016 Uiso 1 1 calc R . .
C32 C 0.4705(2) 0.84514(17) 0.60593(12) 0.0200(5) Uani 1 1 d . . .
H32A H 0.5182 0.8890 0.6308 0.030 Uiso 1 1 calc R . .
H32B H 0.4233 0.8049 0.6333 0.030 Uiso 1 1 calc R . .
H32C H 0.4171 0.8809 0.5787 0.030 Uiso 1 1 calc R . .
C33 C 0.4337(2) 0.53233(16) 0.73945(10) 0.0154(4) Uani 1 1 d . . .
H33A H 0.5122 0.5588 0.7282 0.018 Uiso 1 1 calc R . .
H33B H 0.4454 0.4899 0.7753 0.018 Uiso 1 1 calc R . .
C34 C 0.3500(2) 0.61278(18) 0.75751(12) 0.0215(5) Uani 1 1 d . . .
H34A H 0.3850 0.6485 0.7919 0.032 Uiso 1 1 calc R . .
H34B H 0.2732 0.5866 0.7702 0.032 Uiso 1 1 calc R . .
H34C H 0.3381 0.6548 0.7221 0.032 Uiso 1 1 calc R . .
C35 C 0.2932(2) 0.33456(15) 0.74138(9) 0.0160(4) Uani 1 1 d . . .
H35A H 0.2104 0.3117 0.7366 0.019 Uiso 1 1 calc R . .
H35B H 0.2967 0.3743 0.7789 0.019 Uiso 1 1 calc R . .
C36 C 0.3753(2) 0.24984(19) 0.75020(11) 0.0186(4) Uani 1 1 d . . .
H36A H 0.3508 0.2143 0.7868 0.028 Uiso 1 1 calc R . .
H36B H 0.4574 0.2718 0.7557 0.028 Uiso 1 1 calc R . .
H36C H 0.3705 0.2090 0.7138 0.028 Uiso 1 1 calc R . .
N5 N 0.2020(2) 0.77169(16) 0.56378(12) 0.0316(5) Uani 1 1 d . . .
N6 N 0.0899(2) 0.75843(18) 0.37104(12) 0.0330(6) Uani 1 1 d . . .
C38 C 0.0083(2) 0.46298(17) 0.56010(11) 0.0171(5) Uani 1 1 d . . .
H38A H 0.0123 0.4373 0.6006 0.021 Uiso 1 1 calc R . .
C37 C 0.0589(2) 0.54675(17) 0.54885(11) 0.0174(5) Uani 1 1 d . . .
H37A H 0.0997 0.5788 0.5811 0.021 Uiso 1 1 calc R . .
C39 C 0.0522(2) 0.58898(16) 0.48799(12) 0.0171(4) Uani 1 1 d . . .
C40 C 0.1012(2) 0.67599(17) 0.47698(11) 0.0188(5) Uani 1 1 d . . .
C41 C 0.1582(2) 0.72919(18) 0.52490(12) 0.0218(5) Uani 1 1 d . . .
C42 C 0.0954(2) 0.72091(18) 0.41763(13) 0.0237(5) 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'
Zn Zn 0.2839 1.4301 '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 Zn1 N1 89.96(7) . . ?
N2 Zn1 N3 90.02(7) . . ?
N1 Zn1 N3 175.81(7) . . ?
N2 Zn1 N4 173.93(8) . . ?
N1 Zn1 N4 89.70(7) . . ?
N3 Zn1 N4 89.88(7) . . ?
C1 N1 C4 106.39(17) . . ?
C1 N1 Zn1 126.63(14) . . ?
C4 N1 Zn1 126.81(15) . . ?
C16 N2 C19 105.89(18) . . ?
C16 N2 Zn1 126.86(14) . . ?
C19 N2 Zn1 127.20(14) . . ?
C14 N3 C11 106.54(17) . . ?
C14 N3 Zn1 126.43(15) . . ?
C11 N3 Zn1 127.02(15) . . ?
C6 N4 C9 106.15(18) . . ?
C6 N4 Zn1 127.06(14) . . ?
C9 N4 Zn1 126.77(14) . . ?
N1 C1 C20 124.49(19) . . ?
N1 C1 C2 110.26(18) . . ?
C20 C1 C2 125.22(19) . . ?
C3 C2 C1 106.65(19) . . ?
C3 C2 C21 127.4(2) . . ?
C1 C2 C21 125.92(19) . . ?
C2 C3 C4 106.6(2) . . ?
C2 C3 C23 127.8(2) . . ?
C4 C3 C23 125.6(2) . . ?
N1 C4 C5 124.4(2) . . ?
N1 C4 C3 110.06(18) . . ?
C5 C4 C3 125.5(2) . . ?
C6 C5 C4 127.0(2) . . ?
N4 C6 C5 124.59(19) . . ?
N4 C6 C7 110.52(18) . . ?
C5 C6 C7 124.88(19) . . ?
C8 C7 C6 106.63(19) . . ?
C8 C7 C25 128.06(19) . . ?
C6 C7 C25 125.3(2) . . ?
C7 C8 C9 106.53(19) . . ?
C7 C8 C27 127.2(2) . . ?
C9 C8 C27 126.3(2) . . ?
N4 C9 C10 124.59(19) . . ?
N4 C9 C8 110.13(19) . . ?
C10 C9 C8 125.27(19) . . ?
C9 C10 C11 127.3(2) . . ?
N3 C11 C10 124.4(2) . . ?
N3 C11 C12 109.97(19) . . ?
C10 C11 C12 125.7(2) . . ?
C13 C12 C11 107.2(2) . . ?
C13 C12 C29 126.8(2) . . ?
C11 C12 C29 125.9(2) . . ?
C12 C13 C14 105.8(2) . . ?
C12 C13 C31 128.8(2) . . ?
C14 C13 C31 125.40(19) . . ?
N3 C14 C15 125.2(2) . . ?
N3 C14 C13 110.51(18) . . ?
C15 C14 C13 124.2(2) . . ?
C14 C15 C16 126.3(2) . . ?
N2 C16 C15 124.85(19) . . ?
N2 C16 C17 110.65(19) . . ?
C15 C16 C17 124.49(19) . . ?
C18 C17 C16 106.50(19) . . ?
C18 C17 C33 129.0(2) . . ?
C16 C17 C33 124.3(2) . . ?
C17 C18 C19 106.47(18) . . ?
C17 C18 C35 127.6(2) . . ?
C19 C18 C35 125.91(19) . . ?
N2 C19 C20 124.49(19) . . ?
N2 C19 C18 110.46(18) . . ?
C20 C19 C18 125.04(19) . . ?
C19 C20 C1 126.8(2) . . ?
C2 C21 C22 113.8(2) . . ?
C3 C23 C24 112.8(2) . . ?
C7 C25 C26 112.9(2) . . ?
C8 C27 C28 114.4(2) . . ?
C12 C29 C30 112.5(2) . . ?
C13 C31 C32 114.2(2) . . ?
C17 C33 C34 111.7(2) . . ?
C18 C35 C36 113.5(2) . . ?
C37 C38 C39 121.3(2) . 3_566 ?
C38 C37 C39 120.8(2) . . ?
C40 C39 C38 121.4(2) . 3_566 ?
C40 C39 C37 120.7(2) . . ?
C38 C39 C37 117.9(2) 3_566 . ?
C39 C40 C41 121.7(2) . . ?
C39 C40 C42 122.5(2) . . ?
C41 C40 C42 115.7(2) . . ?
N5 C41 C40 178.9(3) . . ?
N6 C42 C40 178.5(3) . . ?
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
Zn1 N2 2.028(2) . ?
Zn1 N1 2.0370(18) . ?
Zn1 N3 2.0384(19) . ?
Zn1 N4 2.040(2) . ?
N1 C1 1.370(3) . ?
N1 C4 1.372(3) . ?
N2 C16 1.367(3) . ?
N2 C19 1.368(3) . ?
N3 C14 1.363(3) . ?
N3 C11 1.370(3) . ?
N4 C6 1.367(3) . ?
N4 C9 1.371(3) . ?
C1 C20 1.397(3) . ?
C1 C2 1.444(3) . ?
C2 C3 1.368(3) . ?
C2 C21 1.502(3) . ?
C3 C4 1.448(3) . ?
C3 C23 1.499(3) . ?
C4 C5 1.394(3) . ?
C5 C6 1.388(3) . ?
C6 C7 1.449(3) . ?
C7 C8 1.359(3) . ?
C7 C25 1.502(3) . ?
C8 C9 1.455(3) . ?
C8 C27 1.506(3) . ?
C9 C10 1.391(3) . ?
C10 C11 1.392(3) . ?
C11 C12 1.443(3) . ?
C12 C13 1.368(3) . ?
C12 C29 1.497(3) . ?
C13 C14 1.454(3) . ?
C13 C31 1.493(3) . ?
C14 C15 1.391(3) . ?
C15 C16 1.392(3) . ?
C16 C17 1.451(3) . ?
C17 C18 1.358(3) . ?
C17 C33 1.500(3) . ?
C18 C19 1.454(3) . ?
C18 C35 1.496(3) . ?
C19 C20 1.392(3) . ?
C21 C22 1.526(3) . ?
C23 C24 1.525(4) . ?
C25 C26 1.518(4) . ?
C27 C28 1.516(4) . ?
C29 C30 1.532(3) . ?
C31 C32 1.529(3) . ?
C33 C34 1.530(4) . ?
C35 C36 1.526(3) . ?
N5 C41 1.144(4) . ?
N6 C42 1.142(4) . ?
C38 C37 1.339(4) . ?
C38 C39 1.443(3) 3_566 ?
C37 C39 1.449(3) . ?
C39 C40 1.372(3) . ?
C39 C38 1.443(3) 3_566 ?
C40 C41 1.431(3) . ?
C40 C42 1.435(4) . ?
