An I<sub>2</sub>-DMSO catalytic manifold enabled aromatization for C-ring editing of podophyllotoxone.
Yuan, Peng; Liu, Rui; Zhu, Hui-Min; Liao, Zhixin; Xiang, Jia-Chen; Wu, An-Xin; Organic & biomolecular chemistry 21 (2023) 6468–6473; doi:10.1039/d3ob00927k

data_7159495
_publ_section_title
;
 An I<sub>2</sub>-DMSO catalytic manifold enabled aromatization for C-ring
 editing of podophyllotoxone.
;
_journal_issue                   32
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6468
_journal_page_last               6473
_journal_paper_doi               10.1039/d3ob00927k
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C28 H22 Cl N O7, C H Cl3'
_chemical_formula_sum            'C29 H23 Cl4 N O7'
_chemical_formula_weight         639.28
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-04-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-05-11 deposited with the CCDC.	2023-07-28 downloaded from the CCDC.
;
_cell_angle_alpha                110.796(2)
_cell_angle_beta                 90.433(2)
_cell_angle_gamma                91.711(2)
_cell_formula_units_Z            1
_cell_length_a                   5.7924(3)
_cell_length_b                   11.1413(5)
_cell_length_c                   12.0240(6)
_cell_measurement_reflns_used    7438
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.54
_cell_measurement_theta_min      3.10
_cell_volume                     724.95(6)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0490
_diffrn_reflns_av_unetI/netI     0.0444
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            18929
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.003
_diffrn_reflns_theta_max         25.003
_diffrn_reflns_theta_min         2.143
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.456
_exptl_absorpt_correction_T_max  0.0277
_exptl_absorpt_correction_T_min  0.0110
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0780 before and 0.0643 after correction.
The Ratio of minimum to maximum transmission is 0.3971.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.592
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details
;
 Flack x determined using 1904 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     373
_refine_ls_number_reflns         5060
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.112
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0526
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0894P)^2^+0.0290P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1352
_refine_ls_wR_factor_ref         0.1408
_reflns_Friedel_coverage         0.995
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                4393
_reflns_number_total             5060
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00927k2.cif
_cod_data_source_block           mo_0428_2_0m
_cod_depositor_comments
'Adding full bibliography for 7159495--7159496.cif.'
_cod_database_code               7159495
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.969
_shelx_estimated_absorpt_t_min   0.952
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C29(H29)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C2(H2), C4(H4), C5(H5), C14(H14), C18(H18), C21(H21), C25(H25)
2.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C)
;
_shelx_res_checksum              27818
_olex2_submission_special_instructions 'No special instructions were received'