#------------------------------------------------------------------------------
#$Date: 2019-05-14 03:34:26 +0300 (Tue, 14 May 2019) $
#$Revision: 215118 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/34/7123427.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_7123427
loop_
_publ_author_name
'Ambhore, Madan'
'Basavarajappa, Ashokkumar'
'Anand, Venkataramanarao Govindan'
_publ_section_title
;
 Wide-Range Redox States of Core-Modified Expanded Porphyrinoids
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC02326G
_journal_year                    2019
_chemical_formula_moiety         'C66 H22 F20 N2 S4, 2(Cl6 Sb)'
_chemical_formula_sum            'C66 H22 Cl12 F20 N2 S4 Sb2'
_chemical_formula_weight         2020.02
_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
;
2019-02-16 deposited with the CCDC.    2019-05-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.478(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.5683(14)
_cell_length_b                   16.3145(19)
_cell_length_c                   22.437(3)
_cell_measurement_reflns_used    9986
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      23.74
_cell_measurement_theta_min      2.18
_cell_volume                     4163.9(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0615
_diffrn_reflns_av_unetI/netI     0.0610
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            64464
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.329
_diffrn_reflns_theta_min         1.552
_exptl_absorpt_coefficient_mu    1.217
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.611
_exptl_crystal_description       cube
_exptl_crystal_F_000             1964
_refine_diff_density_max         1.403
_refine_diff_density_min         -1.220
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     478
_refine_ls_number_reflns         10334
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0920
_refine_ls_R_factor_gt           0.0547
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0767P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1435
_refine_ls_wR_factor_ref         0.1551
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6094
_reflns_number_total             10379
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9cc02326g2.cif
_cod_data_source_block           4a
_cod_database_code               7123427
_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.
;
_platon_squeeze_void_probe_radius 1.20
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
Sb1 Sb 0.11704(3) 0.73419(2) 0.42589(2) 0.04633(12) Uani 1 1 d . .
S1 S 1.19517(9) 0.60825(7) 0.63488(4) 0.0332(2) Uani 1 1 d . .
S2 S 0.69661(9) 0.53618(7) 0.41506(4) 0.0385(3) Uani 1 1 d . .
Cl4 Cl 0.26105(12) 0.66244(8) 0.49548(5) 0.0563(3) Uani 1 1 d . .
Cl6 Cl 0.15010(13) 0.64308(9) 0.34873(5) 0.0624(4) Uani 1 1 d . .
Cl5 Cl 0.26819(18) 0.81655(13) 0.40038(6) 0.1116(8) Uani 1 1 d . .
Cl2 Cl -0.01975(18) 0.80777(14) 0.35605(8) 0.1082(7) Uani 1 1 d . .
Cl3 Cl -0.02521(17) 0.64211(16) 0.44942(10) 0.1141(8) Uani 1 1 d . .
Cl1 Cl 0.0945(3) 0.82154(16) 0.50535(9) 0.1527(12) Uani 1 1 d . .
F1 F 0.5559(3) 0.65932(17) 0.60782(11) 0.0539(7) Uani 1 1 d . .
F10 F 0.7984(3) 0.70442(19) 0.71126(12) 0.0573(7) Uani 1 1 d . .
F6 F 1.1242(3) 0.84435(17) 0.66003(13) 0.0582(8) Uani 1 1 d . .
F5 F 0.6150(3) 0.7873(2) 0.42821(12) 0.0657(9) Uani 1 1 d . .
F3 F 0.3982(3) 0.91948(19) 0.55656(16) 0.0765(10) Uani 1 1 d . .
N1 N 0.8207(3) 0.6851(2) 0.58151(13) 0.0315(8) Uani 1 1 d . .
F4 F 0.4952(3) 0.91877(19) 0.45560(15) 0.0757(10) Uani 1 1 d . .
F2 F 0.4317(3) 0.7893(2) 0.63394(14) 0.0754(10) Uani 1 1 d . .
F7 F 1.0609(4) 0.98015(19) 0.71405(18) 0.0938(12) Uani 1 1 d . .
F9 F 0.7377(3) 0.8404(2) 0.76529(17) 0.0946(12) Uani 1 1 d . .
F8 F 0.8703(4) 0.9781(2) 0.76894(19) 0.1097(15) Uani 1 1 d . .
C25 C 0.9651(4) 0.7695(3) 0.68403(17) 0.0336(9) Uani 1 1 d . .
C24 C 1.0023(4) 0.6936(2) 0.65728(16) 0.0300(9) Uani 1 1 d . .
C23 C 0.9239(4) 0.6516(2) 0.61306(16) 0.0309(9) Uani 1 1 d . .
C62 C 0.9260(4) 0.5682(3) 0.59344(17) 0.0353(9) Uani 1 1 d . .
H22 H 0.9840 0.5300 0.6079 0.042 Uiso 1 1 calc R U
C13 C 0.6570(4) 0.6463(3) 0.50248(16) 0.0324(9) Uani 1 1 d . .
C2 C 0.5861(4) 0.4537(3) 0.31104(16) 0.0321(9) Uani 1 1 d . .
C60 C 0.6854(4) 0.4045(3) 0.30642(15) 0.0314(9) Uani 1 1 d . .
C3 C 0.4828(3) 0.4489(3) 0.26002(16) 0.0360(10) Uani 1 1 d . .
C31 C 1.1864(4) 0.6782(3) 0.73669(17) 0.0377(10) Uani 1 1 d . .
H31 H 1.1619 0.7101 0.7664 0.045 Uiso 1 1 calc R U
C9 C 0.5772(3) 0.5084(3) 0.35853(16) 0.0329(9) Uani 1 1 d . .
C14 C 0.5881(4) 0.7186(2) 0.51707(16) 0.0331(9) Uani 1 1 d . .
C15 C 0.5415(4) 0.7229(3) 0.56938(18) 0.0381(10) Uani 1 1 d . .
C32 C 1.2937(4) 0.6390(3) 0.74454(16) 0.0373(10) Uani 1 1 d . .
H32 H 1.3479 0.6412 0.7806 0.045 Uiso 1 1 calc R U
C20 C 0.7632(4) 0.6295(3) 0.54119(16) 0.0328(9) Uani 1 1 d . .
C30 C 1.1181(4) 0.6649(2) 0.67924(15) 0.0304(9) Uani 1 1 d . .
C19 C 0.5700(4) 0.7863(3) 0.47912(19) 0.0409(11) Uani 1 1 d . .
C12 C 0.6117(4) 0.6003(3) 0.45006(17) 0.0354(10) Uani 1 1 d . .
C21 C 0.8295(4) 0.5539(3) 0.55014(17) 0.0364(10) Uani 1 1 d . .
H21 H 0.8097 0.5046 0.5300 0.044 Uiso 1 1 calc R U
C015 C 0.8643(4) 0.7714(3) 0.7112(2) 0.0451(11) Uani 1 1 d . .
C4 C 0.4310(4) 0.3739(3) 0.24222(17) 0.0395(10) Uani 1 1 d . .
H4 H 0.4596 0.3263 0.2624 0.047 Uiso 1 1 calc R U
C8 C 0.4395(4) 0.5194(3) 0.22966(19) 0.0464(12) Uani 1 1 d . .
H8 H 0.4737 0.5698 0.2414 0.056 Uiso 1 1 calc R U
C10 C 0.4779(4) 0.5515(3) 0.36838(19) 0.0488(13) Uani 1 1 d . .
H10 H 0.4051 0.5457 0.3432 0.059 Uiso 1 1 calc R U
C18 C 0.5088(4) 0.8535(3) 0.4924(2) 0.0481(12) Uani 1 1 d . .
C26 C 1.0286(4) 0.8414(3) 0.68607(19) 0.0436(11) Uani 1 1 d . .
C17 C 0.4621(5) 0.8549(3) 0.5444(2) 0.0499(12) Uani 1 1 d . .
C16 C 0.4777(5) 0.7893(3) 0.5831(2) 0.0494(12) Uani 1 1 d . .
C27 C 0.9981(5) 0.9115(3) 0.7132(2) 0.0562(13) Uani 1 1 d . .
C11 C 0.4949(4) 0.6027(3) 0.4174(2) 0.0501(13) Uani 1 1 d . .
H11 H 0.4361 0.6355 0.4280 0.060 Uiso 1 1 calc R U
C6 C 0.2934(4) 0.4414(4) 0.1641(2) 0.0600(16) Uani 1 1 d . .
H6 H 0.2298 0.4387 0.1322 0.072 Uiso 1 1 calc R U
C7 C 0.3441(4) 0.5151(4) 0.1812(2) 0.0572(14) Uani 1 1 d . .
H7 H 0.3155 0.5626 0.1608 0.069 Uiso 1 1 calc R U
C5 C 0.3368(4) 0.3702(4) 0.1943(2) 0.0537(14) Uani 1 1 d . .
H5 H 0.3024 0.3199 0.1823 0.064 Uiso 1 1 calc R U
C28 C 0.9033(6) 0.9111(3) 0.7395(3) 0.0695(17) Uani 1 1 d . .
C29 C 0.8329(5) 0.8413(4) 0.7393(2) 0.0626(15) 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'
B B 0.0013 0.0007 '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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sb Sb -0.5866 1.5461 '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
Cl1 Sb1 Cl2 92.43(7) . .
Cl1 Sb1 Cl5 91.62(11) . .
Cl2 Sb1 Cl5 89.21(8) . .
Cl1 Sb1 Cl3 92.20(11) . .
Cl2 Sb1 Cl3 93.57(9) . .
Cl5 Sb1 Cl3 175.18(9) . .
Cl1 Sb1 Cl6 176.72(7) . .
Cl2 Sb1 Cl6 90.68(6) . .
Cl5 Sb1 Cl6 87.40(7) . .
Cl3 Sb1 Cl6 88.62(7) . .
Cl1 Sb1 Cl4 87.77(7) . .
Cl2 Sb1 Cl4 177.94(7) . .
Cl5 Sb1 Cl4 88.73(6) . .
Cl3 Sb1 Cl4 88.48(7) . .
Cl6 Sb1 Cl4 89.08(5) . .
C30 S1 C60 92.86(19) . 3_766
C12 S2 C9 92.7(2) . .
C20 N1 C23 110.3(3) . .
C26 C25 C015 116.3(4) . .
C26 C25 C24 122.3(4) . .
C015 C25 C24 121.4(4) . .
C23 C24 C30 122.3(4) . .
C23 C24 C25 120.1(4) . .
C30 C24 C25 117.6(3) . .
N1 C23 C24 123.9(4) . .
N1 C23 C62 106.2(3) . .
C24 C23 C62 129.8(4) . .
C21 C62 C23 109.0(4) . .
C21 C62 H22 125.5 . .
C23 C62 H22 125.5 . .
C20 C13 C12 124.4(4) . .
C20 C13 C14 117.6(3) . .
C12 C13 C14 118.0(4) . .
C9 C2 C60 125.8(4) . .
C9 C2 C3 116.9(4) . .
C60 C2 C3 117.2(3) . .
C32 C60 C2 127.3(4) 3_766 .
C32 C60 S1 109.0(3) 3_766 3_766
C2 C60 S1 123.6(3) . 3_766
C8 C3 C4 119.5(4) . .
C8 C3 C2 119.9(4) . .
C4 C3 C2 120.6(4) . .
C32 C31 C30 112.9(4) . .
C32 C31 H31 123.5 . .
C30 C31 H31 123.5 . .
C10 C9 C2 127.9(4) . .
C10 C9 S2 108.5(3) . .
C2 C9 S2 123.6(3) . .
C15 C14 C19 116.3(4) . .
C15 C14 C13 122.3(4) . .
C19 C14 C13 121.5(4) . .
F1 C15 C16 118.3(4) . .
F1 C15 C14 119.1(4) . .
C16 C15 C14 122.6(4) . .
C31 C32 C60 114.5(4) . 3_766
C31 C32 H32 122.8 . .
C60 C32 H32 122.8 3_766 .
N1 C20 C13 123.3(4) . .
N1 C20 C21 107.0(3) . .
C13 C20 C21 129.6(4) . .
C31 C30 C24 127.3(4) . .
C31 C30 S1 110.6(3) . .
C24 C30 S1 122.1(3) . .
F5 C19 C18 118.3(4) . .
F5 C19 C14 119.6(4) . .
C18 C19 C14 122.1(4) . .
C13 C12 C11 126.3(4) . .
C13 C12 S2 123.1(3) . .
C11 C12 S2 110.5(3) . .
C62 C21 C20 107.3(4) . .
C62 C21 H21 126.3 . .
C20 C21 H21 126.3 . .
F10 C015 C29 118.6(5) . .
F10 C015 C25 119.9(4) . .
C29 C015 C25 121.5(5) . .
C5 C4 C3 119.9(5) . .
C5 C4 H4 120.0 . .
C3 C4 H4 120.0 . .
C3 C8 C7 120.2(5) . .
C3 C8 H8 119.9 . .
C7 C8 H8 119.9 . .
C11 C10 C9 115.7(4) . .
C11 C10 H10 122.2 . .
C9 C10 H10 122.2 . .
F4 C18 C19 120.7(5) . .
F4 C18 C17 119.4(4) . .
C19 C18 C17 119.9(4) . .
F6 C26 C27 117.5(4) . .
F6 C26 C25 119.4(4) . .
C27 C26 C25 123.1(5) . .
F3 C17 C16 119.9(5) . .
F3 C17 C18 120.1(5) . .
C16 C17 C18 119.9(4) . .
F2 C16 C17 120.7(4) . .
F2 C16 C15 120.1(4) . .
C17 C16 C15 119.2(4) . .
F7 C27 C28 119.1(5) . .
F7 C27 C26 121.6(5) . .
C28 C27 C26 119.3(5) . .
C10 C11 C12 112.6(4) . .
C10 C11 H11 123.7 . .
C12 C11 H11 123.7 . .
C7 C6 C5 120.1(4) . .
C7 C6 H6 120.0 . .
C5 C6 H6 120.0 . .
C6 C7 C8 120.0(5) . .
C6 C7 H7 120.0 . .
C8 C7 H7 120.0 . .
C4 C5 C6 120.3(5) . .
C4 C5 H5 119.9 . .
C6 C5 H5 119.9 . .
C27 C28 F8 122.2(6) . .
C27 C28 C29 121.8(5) . .
F8 C28 C29 115.9(6) . .
F9 C29 C015 119.6(6) . .
F9 C29 C28 122.3(5) . .
C015 C29 C28 118.1(5) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Sb1 Cl1 2.3338(17) .
Sb1 Cl2 2.3449(16) .
Sb1 Cl5 2.3568(16) .
Sb1 Cl3 2.3579(19) .
Sb1 Cl6 2.3650(13) .
Sb1 Cl4 2.3744(13) .
S1 C30 1.721(4) .
S1 C60 1.739(4) 3_766
S2 C12 1.720(4) .
S2 C9 1.757(4) .
F1 C15 1.340(5) .
F10 C015 1.333(6) .
F6 C26 1.342(6) .
F5 C19 1.339(5) .
F3 C17 1.343(5) .
N1 C20 1.365(5) .
N1 C23 1.385(5) .
F4 C18 1.339(5) .
F2 C16 1.345(5) .
F7 C27 1.332(6) .
F9 C29 1.336(6) .
F8 C28 1.368(6) .
C25 C26 1.381(6) .
C25 C015 1.411(6) .
C25 C24 1.474(6) .
C24 C23 1.396(5) .
C24 C30 1.421(6) .
C23 C62 1.433(6) .
C62 C21 1.360(6) .
C62 H22 0.9300 .
C13 C20 1.397(6) .
C13 C12 1.413(5) .
C13 C14 1.492(6) .
C2 C9 1.408(5) .
C2 C60 1.420(6) .
C2 C3 1.500(5) .
C60 C32 1.403(5) 3_766
C60 S1 1.739(4) 3_766
C3 C8 1.384(7) .
C3 C4 1.387(6) .
C31 C32 1.380(6) .
C31 C30 1.401(5) .
C31 H31 0.9300 .
C9 C10 1.398(6) .
C14 C15 1.379(6) .
C14 C19 1.388(6) .
C15 C16 1.377(6) .
C32 C60 1.403(5) 3_766
C32 H32 0.9300 .
C20 C21 1.447(6) .
C19 C18 1.367(6) .
C12 C11 1.416(6) .
C21 H21 0.9300 .
C015 C29 1.383(7) .
C4 C5 1.387(6) .
C4 H4 0.9300 .
C8 C7 1.402(6) .
C8 H8 0.9300 .
C10 C11 1.365(6) .
C10 H10 0.9300 .
C18 C17 1.372(7) .
C26 C27 1.371(7) .
C17 C16 1.369(7) .
C27 C28 1.337(8) .
C11 H11 0.9300 .
C6 C7 1.363(8) .
C6 C5 1.391(8) .
C6 H6 0.9300 .
C7 H7 0.9300 .
C5 H5 0.9300 .
C28 C29 1.400(9) .
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 0.500 256 68 ' '
2 0.000 0.500 1.000 256 68 ' '
3 0.223 0.032 0.811 9 0 ' '
4 0.223 0.468 0.311 9 0 ' '
5 0.427 0.702 0.296 28 0 ' '
6 0.427 0.798 0.796 28 0 ' '
7 0.573 0.202 0.204 29 0 ' '
8 0.573 0.298 0.704 28 0 ' '
9 0.776 0.532 0.689 9 0 ' '
10 0.776 0.968 0.189 9 0 ' '
