Hydrogen-bond-assisted topochemical synthesis of a multivalent zwitterionic tetramer via concomitant cross- and homo [2+2] photocycloadditions. Theoretical antiviral activity against SARS-CoV-2
Escalona, Ana; Heinemann, Frank W.; Briceño, Alexander; Alvarado, Ysaias J.; Paz, José Luis; Lossada, Carla; González-Paz, Lenin; Toro, Robert; Henao, José Antonio; New Journal of Chemistry 47 (2023) 19925–19932; doi:10.1039/D3NJ04041K

data_7062902
_publ_section_title
;
 Hydrogen-bond-assisted topochemical synthesis of a multivalent
 zwitterionic tetramer via concomitant cross- and homo [2+2]
 photocycloadditions. Theoretical antiviral activity against SARS-CoV-2
;
_journal_issue                   43
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              19925
_journal_page_last               19932
_journal_paper_doi               10.1039/D3NJ04041K
_journal_volume                  47
_journal_year                    2023
_chemical_formula_moiety         '6(C2 H6 O S), C30 H22 N2 O16'
_chemical_formula_sum            'C42 H58 N2 O22 S6'
_chemical_formula_weight         1135.26
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2023-03-30
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-03-30 deposited with the CCDC.	2023-09-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.710(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.0803(11)
_cell_length_b                   19.8625(19)
_cell_length_c                   14.0812(14)
_cell_measurement_reflns_used    9924
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.03
_cell_measurement_theta_min      2.39
_cell_volume                     2637.2(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'SHELXTL 6.12 (Bruker AXS, 2002)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXTL 6.12 (Bruker AXS, 2002)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 83.33
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker Kappa APEX II CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Quazar focussing montel optics'
_diffrn_radiation_source         'ImuS micro-focus tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0640
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            72015
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.155
_diffrn_reflns_theta_min         1.855
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.339
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.7138
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0974 before and 0.0531 after correction.
The Ratio of minimum to maximum transmission is 0.9575.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_description       needle
_exptl_crystal_F_000             1192
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.724
_refine_diff_density_min         -0.503
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         5843
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0402
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0334P)^2^+3.2483P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0888
_refine_ls_wR_factor_ref         0.0981
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4586
_reflns_number_total             5843
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3nj04041k2.cif
_cod_data_source_block           meb1505a
_cod_database_code               7062902
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.926
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All N(H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C8(H8), C9(H9), C13(H13)
2.b Me refined with riding coordinates:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,
 H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1A), C3(H3), C4(H4A), C5(H5)
;
_shelx_res_checksum              97893
_olex2_submission_special_instructions 'No special instructions were received'