#------------------------------------------------------------------------------
#$Date: 2024-05-05 03:42:13 +0200 (Sun 05 de May de 2024) $
#$Revision: 291571 $
#$URL: svn://www.crystallography.net/cod/cif/1/57/12/1571213.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_1571213
loop_
_publ_author_name
'Shukla, Pragati'
'Ambhore, Madan D.'
'Anand, Venkataramanarao G.'
_publ_section_title
;
 Open shell (4n + 2)π and closed shell 4nπ
 planar core-modified decaphyrins.
;
_journal_issue                   16
_journal_name_full               'Chemical science'
_journal_page_first              6022
_journal_page_last               6027
_journal_paper_doi               10.1039/d3sc05251f
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C68 H20 F20 O4 S6'
_chemical_formula_sum            'C68 H20 F20 O4 S6'
_chemical_formula_weight         1473.20
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2023-09-07 deposited with the CCDC.	2024-03-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.813(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   18.288(4)
_cell_length_b                   24.723(5)
_cell_length_c                   6.9501(15)
_cell_measurement_reflns_used    8780
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      2.23
_cell_volume                     3138.6(12)
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_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  0.1238
_diffrn_reflns_av_unetI/netI     0.0676
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            67097
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.796
_diffrn_reflns_theta_min         2.230
_exptl_absorpt_coefficient_mu    0.328
_exptl_crystal_colour            Green
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_description       Hexagonal
_exptl_crystal_F_000             1472
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.094
_refine_ls_extinction_coef       0.0092(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   0.915
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     443
_refine_ls_number_reflns         6679
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.915
_refine_ls_R_factor_all          0.1012
_refine_ls_R_factor_gt           0.0649
_refine_ls_shift/su_max          0.028
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0981P)²+6.1779P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1527
_refine_ls_wR_factor_ref         0.1754
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4773
_reflns_number_total             6679
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sc05251f3.cif
_cod_data_source_block           platon_sq
_cod_depositor_comments
'Adding full bibliography for 1571213--1571216.cif.'
_cod_original_cell_volume        3138.6(11)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1571213
_shelx_shelxl_version_number     2017/1
_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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.67614(5) 0.58061(4) 0.32628(13) 0.0239(2) Uani 1 1 d . . . . .
S3 S 0.35756(5) 0.59450(4) 0.56977(13) 0.0253(2) Uani 1 1 d . . . . .
S2 S 0.32375(5) 0.51391(4) 0.02162(13) 0.0261(2) Uani 1 1 d . . . . .
F1 F 0.73906(13) 0.70627(9) 0.3646(3) 0.0337(5) Uani 1 1 d . . . . .
F5 F 0.75657(13) 0.60000(10) 0.9301(3) 0.0400(6) Uani 1 1 d . . . . .
F6 F 0.17326(13) 0.57091(10) 0.9270(4) 0.0378(6) Uani 1 1 d . . . . .
F10 F 0.21867(13) 0.75907(10) 0.8934(3) 0.0374(6) Uani 1 1 d . . . . .
O2 O 0.54765(13) 0.66563(10) 0.7848(3) 0.0225(6) Uani 1 1 d . . . . .
O1 O 0.40375(13) 0.66604(10) 0.8592(3) 0.0235(6) Uani 1 1 d . . . . .
F9 F 0.08877(14) 0.77883(11) 1.0311(4) 0.0474(7) Uani 1 1 d . . . . .
F2 F 0.88388(14) 0.71784(12) 0.3826(4) 0.0544(8) Uani 1 1 d . . . . .
F8 F 0.00067(13) 0.69550(13) 1.1299(4) 0.0567(8) Uani 1 1 d . . . . .
F7 F 0.04546(14) 0.59103(13) 1.0775(5) 0.0601(8) Uani 1 1 d . . . . .
F4 F 0.90061(15) 0.61189(15) 0.9450(5) 0.0692(10) Uani 1 1 d . . . . .
F3 F 0.96604(14) 0.67127(17) 0.6742(5) 0.0802(12) Uani 1 1 d . . . . .
C19 C 0.62438(19) 0.62029(14) 0.4745(5) 0.0213(7) Uani 1 1 d . . . . .
C14 C 0.5259(2) 0.68876(14) 0.9549(5) 0.0227(8) Uani 1 1 d . . . . .
C2 C 0.4378(2) 0.46474(15) 0.1598(5) 0.0240(8) Uani 1 1 d . . . . .
H2 H 0.480078 0.442443 0.171924 0.029 Uiso 1 1 calc R U . . .
C18 C 0.65957(19) 0.64746(14) 0.6390(5) 0.0220(8) Uani 1 1 d . . . . .
C4 C 0.3515(2) 0.52603(15) 0.2593(5) 0.0231(8) Uani 1 1 d . . . . .
C20 C 0.5518(2) 0.61943(15) 0.4108(5) 0.0239(8) Uani 1 1 d . . . . .
H20 H 0.514351 0.638388 0.472631 0.029 Uiso 1 1 calc R U . . .
C1 C 0.3939(2) 0.46855(15) -0.0072(5) 0.0234(8) Uani 1 1 d . . . . .
C22 C 0.6001(2) 0.56355(15) 0.1804(5) 0.0227(8) Uani 1 1 d . . . . .
C13 C 0.4533(2) 0.68850(15) 0.9925(5) 0.0243(8) Uani 1 1 d . . . . .
C21 C 0.5389(2) 0.58760(14) 0.2448(5) 0.0222(8) Uani 1 1 d . . . . .
H21 H 0.491730 0.583278 0.183177 0.027 Uiso 1 1 calc R U . . .
C23 C 0.74144(19) 0.65279(15) 0.6466(5) 0.0224(8) Uani 1 1 d . . . . .
C3 C 0.4137(2) 0.49706(15) 0.3093(5) 0.0237(8) Uani 1 1 d . . . . .
H3 H 0.437886 0.498803 0.433222 0.028 Uiso 1 1 calc R U . . .
C28 C 0.7779(2) 0.68196(15) 0.5104(5) 0.0268(8) Uani 1 1 d . . . . .
C8 C 0.2774(2) 0.62222(16) 0.6498(5) 0.0255(8) Uani 1 1 d . . . . .
C17 C 0.62330(19) 0.66836(14) 0.7889(5) 0.0223(8) Uani 1 1 d . . . . .
C16 C 0.6479(2) 0.69472(15) 0.9619(5) 0.0240(8) Uani 1 1 d . . . . .
H16 H 0.697359 0.702550 1.000230 0.029 Uiso 1 1 calc R U . . .
C24 C 0.7861(2) 0.62943(17) 0.7920(6) 0.0307(9) Uani 1 1 d . . . . .
C5 C 0.3114(2) 0.56213(16) 0.3806(5) 0.0258(8) Uani 1 1 d . . . . .
C30 C 0.1772(2) 0.71601(17) 0.9362(5) 0.0296(9) Uani 1 1 d . . . . .
C9 C 0.2751(2) 0.65290(16) 0.8275(5) 0.0260(8) Uani 1 1 d . . . . .
C29 C 0.2019(2) 0.66395(17) 0.9034(5) 0.0275(9) Uani 1 1 d . . . . .
C11 C 0.3438(2) 0.69734(16) 1.1150(5) 0.0283(9) Uani 1 1 d . . . . .
H11 H 0.305550 0.706248 1.196949 0.034 Uiso 1 1 calc R U . . .
C15 C 0.5886(2) 0.70669(14) 1.0623(5) 0.0243(8) Uani 1 1 d . . . . .
H15 H 0.589142 0.724146 1.184138 0.029 Uiso 1 1 calc R U . . .
C10 C 0.3349(2) 0.67130(15) 0.9314(5) 0.0251(8) Uani 1 1 d . . . . .
C6 C 0.2381(2) 0.57380(17) 0.3753(5) 0.0314(9) Uani 1 1 d . . . . .
H6 H 0.203856 0.560541 0.279327 0.038 Uiso 1 1 calc R U . . .
C12 C 0.4157(2) 0.70710(16) 1.1522(6) 0.0288(9) Uani 1 1 d . . . . .
H12 H 0.437023 0.723476 1.265186 0.035 Uiso 1 1 calc R U . . .
C7 C 0.2191(2) 0.60769(18) 0.5282(5) 0.0326(9) Uani 1 1 d . . . . .
H7 H 0.170441 0.619438 0.545647 0.039 Uiso 1 1 calc R U . . .
C27 C 0.8520(2) 0.68810(18) 0.5176(6) 0.0361(10) Uani 1 1 d . . . . .
C34 C 0.1543(2) 0.62308(18) 0.9511(6) 0.0321(9) Uani 1 1 d . . . . .
C31 C 0.1099(2) 0.72685(18) 1.0094(6) 0.0337(10) Uani 1 1 d . . . . .
C25 C 0.8608(2) 0.6353(2) 0.8020(7) 0.0418(11) Uani 1 1 d . . . . .
C26 C 0.8934(2) 0.6647(2) 0.6635(7) 0.0455(12) Uani 1 1 d . . . . .
C33 C 0.0876(2) 0.6324(2) 1.0273(6) 0.0393(10) Uani 1 1 d . . . . .
C32 C 0.0648(2) 0.6855(2) 1.0568(6) 0.0400(11) 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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'
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
C22 S1 C19 92.24(17) . . ?
C5 S3 C8 92.16(18) . . ?
C1 S2 C4 92.21(18) . . ?
C17 O2 C14 106.9(3) . . ?
C13 O1 C10 107.3(3) . . ?
C20 C19 C18 130.1(3) . . ?
C20 C19 S1 110.2(3) . . ?
C18 C19 S1 119.7(3) . . ?
C13 C14 O2 118.9(3) . . ?
C13 C14 C15 132.4(3) . . ?
O2 C14 C15 108.7(3) . . ?
C1 C2 C3 113.2(3) . . ?
C1 C2 H2 123.4 . . ?
C3 C2 H2 123.4 . . ?
C17 C18 C19 124.4(3) . . ?
C17 C18 C23 117.5(3) . . ?
C19 C18 C23 118.2(3) . . ?
C3 C4 C5 127.5(3) . . ?
C3 C4 S2 110.6(3) . . ?
C5 C4 S2 121.9(3) . . ?
C19 C20 C21 113.1(3) . . ?
C19 C20 H20 123.4 . . ?
C21 C20 H20 123.4 . . ?
C2 C1 C22 126.5(3) . 3_665 ?
C2 C1 S2 110.6(3) . . ?
C22 C1 S2 122.7(3) 3_665 . ?
C21 C22 C1 127.5(3) . 3_665 ?
C21 C22 S1 110.5(3) . . ?
C1 C22 S1 121.8(3) 3_665 . ?
C14 C13 O1 119.1(3) . . ?
C14 C13 C12 131.7(4) . . ?
O1 C13 C12 109.2(3) . . ?
C22 C21 C20 114.0(3) . . ?
C22 C21 H21 123.0 . . ?
C20 C21 H21 123.0 . . ?
C28 C23 C24 115.3(3) . . ?
C28 C23 C18 122.2(3) . . ?
C24 C23 C18 122.5(3) . . ?
C4 C3 C2 113.4(3) . . ?
C4 C3 H3 123.3 . . ?
C2 C3 H3 123.3 . . ?
F1 C28 C27 117.6(3) . . ?
F1 C28 C23 119.5(3) . . ?
C27 C28 C23 122.9(4) . . ?
C7 C8 C9 127.3(3) . . ?
C7 C8 S3 110.0(3) . . ?
C9 C8 S3 122.6(3) . . ?
C18 C17 O2 119.3(3) . . ?
C18 C17 C16 132.4(3) . . ?
O2 C17 C16 108.3(3) . . ?
C15 C16 C17 108.0(3) . . ?
C15 C16 H16 126.0 . . ?
C17 C16 H16 126.0 . . ?
F5 C24 C25 117.2(4) . . ?
F5 C24 C23 120.2(3) . . ?
C25 C24 C23 122.7(4) . . ?
C6 C5 C4 129.5(4) . . ?
C6 C5 S3 111.4(3) . . ?
C4 C5 S3 119.0(3) . . ?
F10 C30 C31 116.7(4) . . ?
F10 C30 C29 120.3(3) . . ?
C31 C30 C29 123.0(4) . . ?
C10 C9 C8 124.8(3) . . ?
C10 C9 C29 117.7(3) . . ?
C8 C9 C29 117.5(3) . . ?
C34 C29 C30 115.1(3) . . ?
C34 C29 C9 122.6(4) . . ?
C30 C29 C9 122.4(4) . . ?
C12 C11 C10 108.6(3) . . ?
C12 C11 H11 125.7 . . ?
C10 C11 H11 125.7 . . ?
C16 C15 C14 108.1(3) . . ?
C16 C15 H15 125.9 . . ?
C14 C15 H15 125.9 . . ?
C9 C10 O1 119.9(3) . . ?
C9 C10 C11 132.7(3) . . ?
O1 C10 C11 107.4(3) . . ?
C5 C6 C7 112.4(4) . . ?
C5 C6 H6 123.8 . . ?
C7 C6 H6 123.8 . . ?
C11 C12 C13 107.4(3) . . ?
C11 C12 H12 126.3 . . ?
C13 C12 H12 126.3 . . ?
C8 C7 C6 114.0(4) . . ?
C8 C7 H7 123.0 . . ?
C6 C7 H7 123.0 . . ?
F2 C27 C28 119.9(4) . . ?
F2 C27 C26 120.4(4) . . ?
C28 C27 C26 119.7(4) . . ?
F6 C34 C33 116.6(4) . . ?
F6 C34 C29 120.0(3) . . ?
C33 C34 C29 123.4(4) . . ?
F9 C31 C32 120.3(4) . . ?
F9 C31 C30 119.4(4) . . ?
C32 C31 C30 120.3(4) . . ?
F4 C25 C26 121.0(4) . . ?
F4 C25 C24 119.8(4) . . ?
C26 C25 C24 119.2(4) . . ?
F3 C26 C25 119.5(4) . . ?
F3 C26 C27 120.3(4) . . ?
C25 C26 C27 120.2(4) . . ?
F7 C33 C34 120.4(4) . . ?
F7 C33 C32 120.0(4) . . ?
C34 C33 C32 119.5(4) . . ?
F8 C32 C31 120.7(4) . . ?
F8 C32 C33 120.6(4) . . ?
C31 C32 C33 118.7(4) . . ?
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
S1 C22 1.733(4) . ?
S1 C19 1.737(4) . ?
S3 C5 1.724(4) . ?
S3 C8 1.735(4) . ?
S2 C1 1.723(4) . ?
S2 C4 1.730(4) . ?
F1 C28 1.349(4) . ?
F5 C24 1.339(4) . ?
F6 C34 1.348(5) . ?
F10 C30 1.349(5) . ?
O2 C17 1.384(4) . ?
O2 C14 1.389(4) . ?
O1 C13 1.381(4) . ?
O1 C10 1.384(4) . ?
F9 C31 1.353(5) . ?
F2 C27 1.347(5) . ?
F8 C32 1.325(5) . ?
F7 C33 1.338(5) . ?
F4 C25 1.335(5) . ?
F3 C26 1.336(5) . ?
C19 C20 1.379(5) . ?
C19 C18 1.449(5) . ?
C14 C13 1.364(5) . ?
C14 C15 1.410(5) . ?
C2 C1 1.382(5) . ?
C2 C3 1.399(5) . ?
C2 H2 0.9500 . ?
C18 C17 1.364(5) . ?
C18 C23 1.501(5) . ?
C4 C3 1.373(5) . ?
C4 C5 1.452(5) . ?
C20 C21 1.407(5) . ?
C20 H20 0.9500 . ?
C1 C22 1.450(5) 3_665 ?
C22 C21 1.362(5) . ?
C13 C12 1.412(5) . ?
C21 H21 0.9500 . ?
C23 C28 1.386(5) . ?
C23 C24 1.393(5) . ?
C3 H3 0.9500 . ?
C28 C27 1.363(6) . ?
C8 C7 1.375(5) . ?
C8 C9 1.452(5) . ?
C17 C16 1.421(5) . ?
C16 C15 1.350(5) . ?
C16 H16 0.9500 . ?
C24 C25 1.373(6) . ?
C5 C6 1.370(5) . ?
C30 C31 1.381(5) . ?
C30 C29 1.387(6) . ?
C9 C10 1.359(5) . ?
C9 C29 1.487(5) . ?
C29 C34 1.385(6) . ?
C11 C12 1.348(5) . ?
C11 C10 1.431(5) . ?
C11 H11 0.9500 . ?
C15 H15 0.9500 . ?
C6 C7 1.410(5) . ?
C6 H6 0.9500 . ?
C12 H12 0.9500 . ?
C7 H7 0.9500 . ?
C27 C26 1.364(6) . ?
C34 C33 1.372(6) . ?
C31 C32 1.364(6) . ?
C25 C26 1.367(6) . ?
C33 C32 1.396(7) . ?
