#------------------------------------------------------------------------------
#$Date: 2024-09-06 01:57:50 +0200 (Fri 06 de Sep de 2024) $
#$Revision: 294493 $
#$URL: svn://www.crystallography.net/cod/cif/1/57/22/1572216.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_1572216
loop_
_publ_author_name
'Zhu, Mengliang'
'Zhang, Hang'
'Yao, Yuhang'
'Wen, Mingpu'
'Ran, Guangliu'
'Yu, Yi'
'Zhang, Ruijing'
'Liang, Xing-Jie'
'Zhang, Jing'
'Zhang, Wenkai'
'Zhang, Jun-Long'
_publ_section_title
;
 More is different: progressive β-thiolation induced-porphyrin
 aggregation switches singlet oxygen photosensitization.
;
_journal_issue                   34
_journal_name_full               'Chemical science'
_journal_page_first              13841
_journal_page_last               13852
_journal_paper_doi               10.1039/d4sc03642e
_journal_volume                  15
_journal_year                    2024
_chemical_formula_sum            'C42 H6 F20 N4 O3 S'
_chemical_formula_weight         1026.57
_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
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2023-05-09 deposited with the CCDC.	2024-07-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.055(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   15.4250(6)
_cell_length_b                   7.9625(3)
_cell_length_c                   17.8492(8)
_cell_measurement_reflns_used    5103
_cell_measurement_temperature    180.00(10)
_cell_measurement_theta_max      27.0060
_cell_measurement_theta_min      1.5050
_cell_volume                     2072.14(15)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      180.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.859
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0417
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.859
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            14989
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.859
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.514
_diffrn_reflns_theta_min         1.519
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.215
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75384
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.72a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.645
_exptl_crystal_description       plate-like
_exptl_crystal_F_000             1012
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.050
_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     319
_refine_ls_number_reflns         5435
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0845
_refine_ls_R_factor_gt           0.0534
_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)+(0.0402P)²+1.8385P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1191
_refine_ls_wR_factor_ref         0.1299
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3653
_reflns_number_total             5435
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc03642e2.cif
_cod_data_source_block           3_sq_CCDC1
_cod_depositor_comments
'Adding full bibliography for 1572215--1572218.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1572216
_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.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.595
_oxdiff_exptl_absorpt_empirical_full_max 1.320
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.51406(10) 0.5363(2) 0.25529(8) 0.0361(3) Uani 0.5 1 d . . P A 1
F1 F 0.18745(11) 0.6207(2) 0.42149(10) 0.0617(5) Uani 1 1 d . . . . .
F2 F 0.02724(11) 0.5005(2) 0.32684(13) 0.0756(6) Uani 1 1 d . . . . .
F3 F -0.03484(10) 0.5884(2) 0.17100(11) 0.0720(6) Uani 1 1 d . . . . .
F4 F 0.07252(12) 0.7766(3) 0.10956(9) 0.0697(5) Uani 1 1 d . . . . .
F5 F 0.23952(10) 0.8772(2) 0.20269(9) 0.0496(4) Uani 1 1 d . . . . .
F6 F 0.63132(10) 0.38122(18) 0.45333(9) 0.0481(4) Uani 1 1 d . . . . .
F7 F 0.73736(12) 0.16707(19) 0.40478(10) 0.0615(5) Uani 1 1 d . . . . .
F8 F 0.84342(12) 0.2824(2) 0.32107(11) 0.0683(5) Uani 1 1 d . . . . .
F9 F 0.84375(12) 0.6162(2) 0.28697(11) 0.0647(5) Uani 1 1 d . . . . .
F10 F 0.74364(10) 0.83114(18) 0.34066(9) 0.0482(4) Uani 1 1 d . . . . .
O1 O 0.39072(10) 0.6608(2) 0.31231(9) 0.0362(4) Uani 1 1 d . . . . .
O2 O 0.5015(3) 0.5243(6) 0.2818(2) 0.0361(3) Uani 0.5 1 d D . P A 2
N1 N 0.47207(12) 0.8193(2) 0.41714(11) 0.0301(4) Uani 1 1 d . . . . .
N2 N 0.64061(11) 0.9649(2) 0.52057(11) 0.0301(4) Uani 1 1 d . . . . .
H2 H 0.5823 0.9936 0.5050 0.036 Uiso 1 1 calc R U . . .
C1 C 0.30322(14) 0.8311(3) 0.36991(13) 0.0321(5) Uani 1 1 d . . . . .
C2 C 0.38927(15) 0.7755(3) 0.36972(13) 0.0309(5) Uani 1 1 d . . . . .
C3 C 0.48234(15) 0.6310(3) 0.32235(13) 0.0337(5) Uani 1 1 d D . . . .
C4 C 0.53255(14) 0.7302(3) 0.39188(13) 0.0296(5) Uani 1 1 d . . . . .
C5 C 0.62781(14) 0.7317(3) 0.42670(13) 0.0302(5) Uani 1 1 d . . . . .
C6 C 0.67647(14) 0.8375(3) 0.48851(13) 0.0304(5) Uani 1 1 d . . . . .
C7 C 0.77262(15) 0.8337(3) 0.53144(14) 0.0360(5) Uani 1 1 d . . . . .
H7 H 0.8156 0.7570 0.5228 0.043 Uiso 1 1 calc R U . . .
C8 C 0.79195(15) 0.9570(3) 0.58615(15) 0.0373(5) Uani 1 1 d . . . . .
H8 H 0.8509 0.9834 0.6222 0.045 Uiso 1 1 calc R U . . .
C9 C 0.70806(14) 1.0412(3) 0.58025(13) 0.0313(5) Uani 1 1 d . . . . .
C10 C 0.21797(14) 0.7548(3) 0.31494(14) 0.0340(5) Uani 1 1 d . . . . .
C11 C 0.16143(16) 0.6588(3) 0.34427(15) 0.0416(6) Uani 1 1 d . . . . .
C12 C 0.07823(16) 0.5965(3) 0.29598(19) 0.0492(7) Uani 1 1 d . . . . .
C13 C 0.04836(16) 0.6369(3) 0.21708(17) 0.0484(7) Uani 1 1 d . . . . .
C14 C 0.10299(18) 0.7306(4) 0.18625(15) 0.0470(7) Uani 1 1 d . . . . .
C15 C 0.18754(16) 0.7859(3) 0.23457(14) 0.0365(5) Uani 1 1 d . . . . .
C16 C 0.68431(14) 0.6121(3) 0.39809(13) 0.0319(5) Uani 1 1 d . . . . .
C17 C 0.68427(15) 0.4412(3) 0.41290(14) 0.0368(5) Uani 1 1 d . . . . .
C18 C 0.73738(18) 0.3309(3) 0.38778(16) 0.0435(6) Uani 1 1 d . . . . .
C19 C 0.79125(18) 0.3897(4) 0.34533(16) 0.0473(6) Uani 1 1 d . . . . .
C20 C 0.79242(17) 0.5577(4) 0.32875(16) 0.0450(6) Uani 1 1 d . . . . .
C21 C 0.74015(16) 0.6668(3) 0.35575(15) 0.0375(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'
F F 0.0171 0.0103 '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'
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
C2 O1 C3 106.31(17) . . ?
C2 N1 C4 105.80(18) . . ?
C9 N2 C6 110.34(17) . . ?
C9 N2 H2 124.8 . . ?
C6 N2 H2 124.8 . . ?
C9 C1 C2 123.1(2) 3_676 . ?
C9 C1 C10 116.68(19) 3_676 . ?
C2 C1 C10 120.2(2) . . ?
N1 C2 O1 113.73(18) . . ?
N1 C2 C1 129.1(2) . . ?
O1 C2 C1 117.19(19) . . ?
O2 C3 O1 118.6(3) . . ?
O2 C3 C4 136.1(3) . . ?
O1 C3 C4 104.64(18) . . ?
O1 C3 S1 121.70(17) . . ?
C4 C3 S1 132.45(18) . . ?
N1 C4 C5 125.7(2) . . ?
N1 C4 C3 109.43(18) . . ?
C5 C4 C3 124.9(2) . . ?
C4 C5 C6 125.0(2) . . ?
C4 C5 C16 119.4(2) . . ?
C6 C5 C16 115.66(18) . . ?
N2 C6 C5 126.28(19) . . ?
N2 C6 C7 106.38(19) . . ?
C5 C6 C7 127.3(2) . . ?
C8 C7 C6 108.5(2) . . ?
C8 C7 H7 125.7 . . ?
C6 C7 H7 125.7 . . ?
C7 C8 C9 107.9(2) . . ?
C7 C8 H8 126.1 . . ?
C9 C8 H8 126.1 . . ?
N2 C9 C1 126.77(19) . 3_676 ?
N2 C9 C8 106.8(2) . . ?
C1 C9 C8 126.2(2) 3_676 . ?
C15 C10 C11 116.7(2) . . ?
C15 C10 C1 122.7(2) . . ?
C11 C10 C1 120.4(2) . . ?
F1 C11 C12 117.7(2) . . ?
F1 C11 C10 120.0(2) . . ?
C12 C11 C10 122.2(2) . . ?
F2 C12 C13 120.8(2) . . ?
F2 C12 C11 119.9(3) . . ?
C13 C12 C11 119.3(3) . . ?
F3 C13 C14 120.3(3) . . ?
F3 C13 C12 119.9(3) . . ?
C14 C13 C12 119.8(2) . . ?
F4 C14 C13 120.1(2) . . ?
F4 C14 C15 119.6(3) . . ?
C13 C14 C15 120.2(2) . . ?
F5 C15 C10 119.5(2) . . ?
F5 C15 C14 118.9(2) . . ?
C10 C15 C14 121.6(2) . . ?
C17 C16 C21 116.8(2) . . ?
C17 C16 C5 121.7(2) . . ?
C21 C16 C5 121.5(2) . . ?
F6 C17 C18 118.8(2) . . ?
F6 C17 C16 119.3(2) . . ?
C18 C17 C16 121.9(2) . . ?
F7 C18 C17 120.3(2) . . ?
F7 C18 C19 120.0(2) . . ?
C17 C18 C19 119.7(2) . . ?
F8 C19 C20 120.1(3) . . ?
F8 C19 C18 119.7(3) . . ?
C20 C19 C18 120.2(2) . . ?
F9 C20 C19 120.8(2) . . ?
F9 C20 C21 119.8(2) . . ?
C19 C20 C21 119.3(2) . . ?
F10 C21 C20 118.7(2) . . ?
F10 C21 C16 119.2(2) . . ?
C20 C21 C16 122.1(2) . . ?
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 C3 1.620(3) . ?
F1 C11 1.339(3) . ?
F2 C12 1.338(3) . ?
F3 C13 1.335(3) . ?
F4 C14 1.345(3) . ?
F5 C15 1.339(3) . ?
F6 C17 1.342(3) . ?
F7 C18 1.340(3) . ?
F8 C19 1.339(3) . ?
F9 C20 1.336(3) . ?
F10 C21 1.340(3) . ?
O1 C2 1.378(3) . ?
O1 C3 1.386(3) . ?
O2 C3 1.214(5) . ?
N1 C2 1.328(3) . ?
N1 C4 1.361(3) . ?
N2 C9 1.365(3) . ?
N2 C6 1.367(3) . ?
N2 H2 0.8800 . ?
C1 C9 1.398(3) 3_676 ?
C1 C2 1.400(3) . ?
C1 C10 1.490(3) . ?
C3 C4 1.461(3) . ?
C4 C5 1.396(3) . ?
C5 C6 1.396(3) . ?
C5 C16 1.489(3) . ?
C6 C7 1.430(3) . ?
C7 C8 1.348(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.430(3) . ?
C8 H8 0.9500 . ?
C9 C1 1.398(3) 3_676 ?
C10 C15 1.378(3) . ?
C10 C11 1.385(3) . ?
C11 C12 1.383(3) . ?
C12 C13 1.369(4) . ?
C13 C14 1.368(4) . ?
C14 C15 1.380(3) . ?
C16 C17 1.387(3) . ?
C16 C21 1.389(3) . ?
C17 C18 1.372(3) . ?
C18 C19 1.376(4) . ?
C19 C20 1.372(4) . ?
C20 C21 1.375(3) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N1 C2 O1 -0.6(2) . . . . ?
C4 N1 C2 C1 -179.6(2) . . . . ?
C3 O1 C2 N1 -1.5(2) . . . . ?
C3 O1 C2 C1 177.6(2) . . . . ?
C9 C1 C2 N1 5.3(4) 3_676 . . . ?
C10 C1 C2 N1 -175.1(2) . . . . ?
C9 C1 C2 O1 -173.7(2) 3_676 . . . ?
C10 C1 C2 O1 5.9(3) . . . . ?
C2 O1 C3 O2 174.9(3) . . . . ?
C2 O1 C3 C4 2.8(2) . . . . ?
C2 O1 C3 S1 -166.11(18) . . . . ?
C2 N1 C4 C5 -177.3(2) . . . . ?
C2 N1 C4 C3 2.4(2) . . . . ?
O2 C3 C4 N1 -173.3(4) . . . . ?
O1 C3 C4 N1 -3.3(2) . . . . ?
S1 C3 C4 N1 163.8(2) . . . . ?
O2 C3 C4 C5 6.4(5) . . . . ?
O1 C3 C4 C5 176.4(2) . . . . ?
S1 C3 C4 C5 -16.4(4) . . . . ?
N1 C4 C5 C6 -6.4(4) . . . . ?
C3 C4 C5 C6 173.8(2) . . . . ?
N1 C4 C5 C16 172.8(2) . . . . ?
C3 C4 C5 C16 -6.9(3) . . . . ?
C9 N2 C6 C5 179.7(2) . . . . ?
C9 N2 C6 C7 0.4(2) . . . . ?
C4 C5 C6 N2 -5.7(4) . . . . ?
C16 C5 C6 N2 175.0(2) . . . . ?
C4 C5 C6 C7 173.4(2) . . . . ?
C16 C5 C6 C7 -5.9(3) . . . . ?
N2 C6 C7 C8 -0.8(3) . . . . ?
C5 C6 C7 C8 179.9(2) . . . . ?
C6 C7 C8 C9 0.9(3) . . . . ?
C6 N2 C9 C1 -175.5(2) . . . 3_676 ?
C6 N2 C9 C8 0.2(3) . . . . ?
C7 C8 C9 N2 -0.7(3) . . . . ?
C7 C8 C9 C1 175.1(2) . . . 3_676 ?
C9 C1 C10 C15 106.9(3) 3_676 . . . ?
C2 C1 C10 C15 -72.7(3) . . . . ?
C9 C1 C10 C11 -67.8(3) 3_676 . . . ?
C2 C1 C10 C11 112.6(3) . . . . ?
C15 C10 C11 F1 178.6(2) . . . . ?
C1 C10 C11 F1 -6.4(4) . . . . ?
C15 C10 C11 C12 -0.1(4) . . . . ?
C1 C10 C11 C12 174.9(2) . . . . ?
F1 C11 C12 F2 -0.6(4) . . . . ?
C10 C11 C12 F2 178.2(2) . . . . ?
F1 C11 C12 C13 178.3(2) . . . . ?
C10 C11 C12 C13 -3.0(4) . . . . ?
F2 C12 C13 F3 3.9(4) . . . . ?
C11 C12 C13 F3 -174.9(2) . . . . ?
F2 C12 C13 C14 -177.8(2) . . . . ?
C11 C12 C13 C14 3.4(4) . . . . ?
F3 C13 C14 F4 1.0(4) . . . . ?
C12 C13 C14 F4 -177.2(2) . . . . ?
F3 C13 C14 C15 177.6(2) . . . . ?
C12 C13 C14 C15 -0.7(4) . . . . ?
C11 C10 C15 F5 -179.6(2) . . . . ?
C1 C10 C15 F5 5.5(3) . . . . ?
C11 C10 C15 C14 2.9(3) . . . . ?
C1 C10 C15 C14 -172.0(2) . . . . ?
F4 C14 C15 F5 -3.5(3) . . . . ?
C13 C14 C15 F5 179.9(2) . . . . ?
F4 C14 C15 C10 174.0(2) . . . . ?
C13 C14 C15 C10 -2.6(4) . . . . ?
C4 C5 C16 C17 -70.5(3) . . . . ?
C6 C5 C16 C17 108.8(3) . . . . ?
C4 C5 C16 C21 110.0(3) . . . . ?
C6 C5 C16 C21 -70.7(3) . . . . ?
C21 C16 C17 F6 -179.8(2) . . . . ?
C5 C16 C17 F6 0.7(3) . . . . ?
C21 C16 C17 C18 0.6(4) . . . . ?
C5 C16 C17 C18 -178.9(2) . . . . ?
F6 C17 C18 F7 -1.2(4) . . . . ?
C16 C17 C18 F7 178.4(2) . . . . ?
F6 C17 C18 C19 179.2(2) . . . . ?
C16 C17 C18 C19 -1.2(4) . . . . ?
F7 C18 C19 F8 0.1(4) . . . . ?
C17 C18 C19 F8 179.7(2) . . . . ?
F7 C18 C19 C20 -179.1(2) . . . . ?
C17 C18 C19 C20 0.5(4) . . . . ?
F8 C19 C20 F9 1.4(4) . . . . ?
C18 C19 C20 F9 -179.4(2) . . . . ?
F8 C19 C20 C21 -178.4(2) . . . . ?
C18 C19 C20 C21 0.8(4) . . . . ?
F9 C20 C21 F10 -1.4(4) . . . . ?
C19 C20 C21 F10 178.5(2) . . . . ?
F9 C20 C21 C16 178.7(2) . . . . ?
C19 C20 C21 C16 -1.4(4) . . . . ?
C17 C16 C21 F10 -179.2(2) . . . . ?
C5 C16 C21 F10 0.4(3) . . . . ?
C17 C16 C21 C20 0.7(4) . . . . ?
C5 C16 C21 C20 -179.8(2) . . . . ?
