#------------------------------------------------------------------------------
#$Date: 2019-11-26 05:41:54 +0200 (Tue, 26 Nov 2019) $
#$Revision: 242740 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/28/4132848.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_4132848
loop_
_publ_author_name
'Sarma, Tridib'
'Kim, Gakhyun'
'Sen, Sajal'
'Cha, Won-Young'
'Duan, Zhiming'
'Moore, Matthew D.'
'Lynch, Vincent M.'
'Zhang, Zhan'
'Kim, Dongho'
'Sessler, Jonathan L.'
_publ_section_title
;
 Proton-Coupled Redox Switching in an Annulated π-Extended Core-Modified
 Octaphyrin.
;
_journal_issue                   38
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12111
_journal_page_last               12119
_journal_paper_doi               10.1021/jacs.8b06938
_journal_volume                  140
_journal_year                    2018
_chemical_formula_sum            'C42 H30 N2 S3'
_chemical_formula_weight         658.86
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-06-03 deposited with the CCDC.
2018-06-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 115.79(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.511(3)
_cell_length_b                   27.674(6)
_cell_length_c                   14.945(3)
_cell_measurement_reflns_used    65842
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.55
_cell_measurement_theta_min      1.55
_cell_volume                     5031(2)
_computing_cell_refinement       HKL3000
_computing_data_collection
;
marccd, control software for MarCCD-300 detector
;
_computing_data_reduction        HKL3000
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type
;
Shanghai Synchrotron Radiation Facility, beam line station 
BL17B equipped with a MarCCD-300 detector
;
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.6525
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            23820
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        23.048
_diffrn_reflns_theta_max         26.554
_diffrn_reflns_theta_min         1.545
_diffrn_source                   synchrotron
_exptl_absorpt_coefficient_mu    0.135
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements
Sortav (Blessing 1995, 1997)
;
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    0.870
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.065
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.967
_refine_diff_density_min         -0.651
_refine_diff_density_rms         0.140
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     430
_refine_ls_number_reflns         13193
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.1368
_refine_ls_R_factor_gt           0.1272
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1301P)²+42.1761P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3594
_refine_ls_wR_factor_ref         0.3649
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11373
_reflns_number_total             13193
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja8b06938_si_004.cif
_cod_data_source_block           a_sq
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4132848
_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.
;
_shelx_estimated_absorpt_t_min   0.991
_shelx_estimated_absorpt_t_max   0.997
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
S1 S -0.01436(11) 0.89496(5) 0.86432(10) 0.0289(3) Uani 1 1 d . .
S2 S 0.18899(13) 0.88619(5) 0.71780(12) 0.0375(3) Uani 1 1 d . .
S3 S 0.17300(11) 1.00814(5) 0.87827(10) 0.0286(3) Uani 1 1 d . .
N1 N 0.2518(4) 1.10964(17) 0.9357(4) 0.0329(10) Uani 1 1 d . .
N2 N 0.1736(4) 1.16116(17) 1.0796(4) 0.0316(9) Uani 1 1 d . .
C1 C -0.0368(5) 0.83928(19) 0.8039(4) 0.0302(10) Uani 1 1 d . .
C2 C 0.0294(5) 0.8330(2) 0.7537(4) 0.0314(11) Uani 1 1 d . .
H2 H 0.0296 0.8049 0.7173 0.038 Uiso 1 1 calc R U
C3 C 0.0937(5) 0.8729(2) 0.7645(4) 0.0320(11) Uani 1 1 d . .
C4 C 0.0815(4) 0.91036(19) 0.8211(4) 0.0287(10) Uani 1 1 d . .
C5 C 0.1481(5) 0.95074(19) 0.8261(4) 0.0293(10) Uani 1 1 d . .
C6 C 0.2110(5) 0.9421(2) 0.7742(5) 0.0334(11) Uani 1 1 d . .
C7 C 0.2750(5) 0.9813(2) 0.7722(4) 0.0330(11) Uani 1 1 d . .
H7 H 0.3217 0.9809 0.7396 0.040 Uiso 1 1 calc R U
C8 C 0.2625(4) 1.02093(19) 0.8234(4) 0.0273(10) Uani 1 1 d . .
C9 C 0.3138(5) 1.10646(19) 0.8813(4) 0.0304(10) Uani 1 1 d . .
C10 C 0.3757(5) 1.1500(2) 0.8882(4) 0.0338(11) Uani 1 1 d . .
H10 H 0.4220 1.1563 0.8566 0.041 Uiso 1 1 calc R U
C11 C 0.3541(5) 1.18041(19) 0.9496(4) 0.0298(10) Uani 1 1 d . .
C12 C 0.3932(4) 1.2292(2) 0.9855(4) 0.0308(10) Uani 1 1 d . .
C13 C 0.4648(5) 1.2536(2) 0.9541(4) 0.0339(11) Uani 1 1 d . .
H13 H 0.4900 1.2382 0.9110 0.041 Uiso 1 1 calc R U
C14 C 0.4976(5) 1.3003(2) 0.9869(5) 0.0371(12) Uani 1 1 d . .
H14 H 0.5499 1.3160 0.9702 0.044 Uiso 1 1 calc R U
C15 C 0.4552(5) 1.3246(2) 1.0436(5) 0.0383(12) Uani 1 1 d . .
H15 H 0.4721 1.3577 1.0600 0.046 Uiso 1 1 calc R U
C16 C 0.3869(5) 1.2994(2) 1.0766(5) 0.0365(12) Uani 1 1 d . .
H16 H 0.3607 1.3150 1.1188 0.044 Uiso 1 1 calc R U
C17 C 0.3576(5) 1.2522(2) 1.0481(4) 0.0326(11) Uani 1 1 d . .
C18 C 0.2850(4) 1.22511(19) 1.0806(4) 0.0292(10) Uani 1 1 d . .
C19 C 0.2458(5) 1.23717(19) 1.1485(4) 0.0311(10) Uani 1 1 d . .
H19 H 0.2624 1.2655 1.1882 0.037 Uiso 1 1 calc R U
C20 C 0.1745(5) 1.1982(2) 1.1472(4) 0.0308(10) Uani 1 1 d . .
C21 C 0.2396(5) 1.1778(2) 1.0426(4) 0.0325(11) Uani 1 1 d . .
C22 C 0.2785(5) 1.15399(19) 0.9771(4) 0.0302(10) Uani 1 1 d . .
C23 C 0.3172(5) 1.0661(2) 0.8295(4) 0.0309(10) Uani 1 1 d . .
C24 C -0.1147(4) 0.80325(19) 0.8001(4) 0.0277(10) Uani 1 1 d . .
C25 C 0.3820(5) 1.06786(19) 0.7711(4) 0.0308(10) Uani 1 1 d . .
C26 C 0.4907(5) 1.05193(19) 0.8103(4) 0.0300(10) Uani 1 1 d . .
C27 C 0.5447(5) 1.0514(2) 0.7482(5) 0.0367(12) Uani 1 1 d . .
H27 H 0.6188 1.0407 0.7747 0.044 Uiso 1 1 calc R U
C28 C 0.4945(5) 1.0656(2) 0.6519(5) 0.0376(12) Uani 1 1 d . .
C29 C 0.3850(5) 1.0825(2) 0.6123(4) 0.0364(12) Uani 1 1 d . .
H29 H 0.3487 1.0926 0.5450 0.044 Uiso 1 1 calc R U
C30 C 0.3303(6) 1.0843(2) 0.6732(5) 0.0431(15) Uani 1 1 d . .
C31 C 0.5468(5) 1.0334(2) 0.9154(4) 0.0379(12) Uani 1 1 d . .
H31A H 0.5252 0.9998 0.9174 0.057 Uiso 1 1 calc R U
H31B H 0.5250 1.0532 0.9582 0.057 Uiso 1 1 calc R U
H31C H 0.6267 1.0352 0.9390 0.057 Uiso 1 1 calc R U
C32 C 0.5552(8) 1.0657(3) 0.5856(7) 0.062(2) Uani 1 1 d . .
H32A H 0.6009 1.0948 0.5992 0.094 Uiso 1 1 calc R U
H32B H 0.5015 1.0655 0.5156 0.094 Uiso 1 1 calc R U
H32C H 0.6019 1.0370 0.5998 0.094 Uiso 1 1 calc R U
C33 C 0.2118(6) 1.1029(3) 0.6283(5) 0.0457(15) Uani 1 1 d . .
H33A H 0.1718 1.0873 0.6617 0.069 Uiso 1 1 calc R U
H33B H 0.1758 1.0952 0.5573 0.069 Uiso 1 1 calc R U
H33C H 0.2119 1.1379 0.6373 0.069 Uiso 1 1 calc R U
C34 C -0.1333(4) 0.7628(2) 0.7270(4) 0.0291(10) Uani 1 1 d . .
C35 C -0.2056(5) 0.7709(2) 0.6264(4) 0.0324(11) Uani 1 1 d . .
C36 C -0.2215(5) 0.7328(2) 0.5604(4) 0.0345(11) Uani 1 1 d . .
H36 H -0.2692 0.7377 0.4922 0.041 Uiso 1 1 calc R U
C37 C -0.1714(5) 0.6882(2) 0.5890(4) 0.0326(11) Uani 1 1 d . .
C38 C -0.1007(5) 0.6812(2) 0.6895(4) 0.0301(10) Uani 1 1 d . .
H38 H -0.0651 0.6509 0.7111 0.036 Uiso 1 1 calc R U
C39 C -0.0820(5) 0.7179(2) 0.7575(4) 0.0306(10) Uani 1 1 d . .
C40 C -0.2622(6) 0.8187(2) 0.5921(5) 0.0442(14) Uani 1 1 d . .
H40A H -0.2976 0.8196 0.5193 0.066 Uiso 1 1 calc R U
H40B H -0.2080 0.8448 0.6175 0.066 Uiso 1 1 calc R U
H40C H -0.3178 0.8228 0.6170 0.066 Uiso 1 1 calc R U
C41 C -0.1905(6) 0.6493(3) 0.5158(5) 0.0452(15) Uani 1 1 d . .
H41A H -0.2145 0.6200 0.5375 0.068 Uiso 1 1 calc R U
H41B H -0.1222 0.6427 0.5101 0.068 Uiso 1 1 calc R U
H41C H -0.2475 0.6594 0.4509 0.068 Uiso 1 1 calc R U
C42 C -0.0048(6) 0.7096(2) 0.8632(5) 0.0430(14) Uani 1 1 d . .
H42A H -0.0451 0.6965 0.8986 0.065 Uiso 1 1 calc R U
H42B H 0.0298 0.7403 0.8936 0.065 Uiso 1 1 calc R U
H42C H 0.0521 0.6866 0.8670 0.065 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 0.0030 0.0010 '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 0.0050 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1080 0.1050 '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
C4 S1 C1 90.8(3) .
C6 S2 C3 89.6(2) .
C5 S3 C8 90.7(2) .
C9 N1 C22 102.4(4) .
C21 N2 C20 104.2(4) .
C24 C1 C2 121.3(5) .
C24 C1 S1 126.4(4) .
C2 C1 S1 112.3(4) .
C3 C2 C1 110.7(5) .
C2 C3 C4 115.8(5) .
C2 C3 S2 131.3(4) .
C4 C3 S2 112.9(4) .
C3 C4 C5 112.3(4) .
C3 C4 S1 110.4(4) .
C5 C4 S1 137.3(4) .
C6 C5 C4 111.2(5) .
C6 C5 S3 111.1(4) .
C4 C5 S3 137.8(4) .
C5 C6 C7 114.3(5) .
C5 C6 S2 114.0(4) .
C7 C6 S2 131.5(4) .
C8 C7 C6 112.1(5) .
C7 C8 C23 122.7(4) .
C7 C8 S3 111.7(4) .
C23 C8 S3 125.6(4) .
C23 C9 N1 123.6(5) .
C23 C9 C10 124.1(5) .
N1 C9 C10 112.3(5) .
C11 C10 C9 106.0(5) .
C10 C11 C22 105.2(5) .
C10 C11 C12 131.6(5) .
C22 C11 C12 123.2(5) .
C17 C12 C13 119.7(5) .
C17 C12 C11 119.7(5) .
C13 C12 C11 120.6(5) .
C14 C13 C12 119.1(5) .
C13 C14 C15 121.0(5) .
C16 C15 C14 118.9(6) .
C17 C16 C15 120.3(5) .
C12 C17 C16 120.6(5) .
C12 C17 C18 118.0(5) .
C16 C17 C18 121.4(5) .
C19 C18 C21 105.9(5) .
C19 C18 C17 130.2(5) .
C21 C18 C17 123.8(5) .
C18 C19 C20 106.2(5) .
C24 C20 C19 125.4(5) 3_577
C24 C20 N2 124.4(5) 3_577
C19 C20 N2 110.2(4) .
N2 C21 C22 129.3(5) .
N2 C21 C18 113.4(5) .
C22 C21 C18 117.1(5) .
N1 C22 C21 128.1(5) .
N1 C22 C11 114.1(4) .
C21 C22 C11 117.9(5) .
C9 C23 C8 127.1(5) .
C9 C23 C25 118.6(5) .
C8 C23 C25 114.3(4) .
C20 C24 C1 127.8(5) 3_577
C20 C24 C34 116.6(5) 3_577
C1 C24 C34 115.7(4) .
C30 C25 C26 119.9(5) .
C30 C25 C23 118.2(5) .
C26 C25 C23 121.8(5) .
C27 C26 C25 118.7(5) .
C27 C26 C31 120.9(5) .
C25 C26 C31 120.3(5) .
C28 C27 C26 122.2(6) .
C27 C28 C29 119.3(5) .
C27 C28 C32 121.6(6) .
C29 C28 C32 119.0(6) .
C30 C29 C28 119.5(6) .
C25 C30 C29 120.3(6) .
C25 C30 C33 121.3(5) .
C29 C30 C33 118.3(6) .
C39 C34 C35 120.2(5) .
C39 C34 C24 121.4(5) .
C35 C34 C24 118.4(5) .
C36 C35 C34 117.2(5) .
C36 C35 C40 121.7(5) .
C34 C35 C40 121.1(5) .
C35 C36 C37 123.5(5) .
C36 C37 C38 118.0(5) .
C36 C37 C41 121.2(5) .
C38 C37 C41 120.8(5) .
C39 C38 C37 120.6(5) .
C38 C39 C34 120.5(5) .
C38 C39 C42 119.3(5) .
C34 C39 C42 120.2(5) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C4 1.734(5) .
S1 C1 1.745(5) .
S2 C6 1.726(6) .
S2 C3 1.750(5) .
S3 C5 1.736(5) .
S3 C8 1.767(5) .
N1 C9 1.401(6) .
N1 C22 1.351(7) .
N2 C21 1.319(7) .
N2 C20 1.435(7) .
C1 C24 1.433(7) .
C1 C2 1.405(7) .
C2 C3 1.372(7) .
C3 C4 1.391(7) .
C4 C5 1.416(7) .
C5 C6 1.397(7) .
C6 C7 1.395(8) .
C7 C8 1.389(7) .
C8 C23 1.435(8) .
C9 C23 1.371(7) .
C9 C10 1.444(8) .
C10 C11 1.366(7) .
C11 C22 1.452(7) .
C11 C12 1.465(7) .
C12 C17 1.379(8) .
C12 C13 1.416(7) .
C13 C14 1.385(8) .
C14 C15 1.386(8) .
C15 C16 1.407(8) .
C16 C17 1.379(8) .
C17 C18 1.475(7) .
C18 C19 1.373(7) .
C18 C21 1.454(8) .
C19 C20 1.441(7) .
C20 C24 1.353(7) 3_577
C21 C22 1.455(7) .
C23 C25 1.482(7) .
C24 C20 1.353(7) 3_577
C24 C34 1.506(7) .
C25 C30 1.395(9) .
C25 C26 1.395(8) .
C26 C27 1.408(7) .
C26 C31 1.506(8) .
C27 C28 1.356(9) .
C28 C29 1.413(9) .
C28 C32 1.537(8) .
C29 C30 1.400(7) .
C30 C33 1.531(10) .
C34 C39 1.400(8) .
C34 C35 1.409(8) .
C35 C36 1.395(8) .
C35 C40 1.502(8) .
C36 C37 1.382(8) .
C37 C38 1.399(8) .
C37 C41 1.476(8) .
C38 C39 1.380(7) .
C39 C42 1.483(8) .
