Formal nucleophilic pyrrolylmethylation via palladium-based auto-tandem catalysis: switchable regiodivergent synthesis and remote chirality transfer
Chen, Zhi; Li, Yu-Fan; Tan, Shun-Zhong; Ouyang, Qin; Chen, Zhi-Chao; Du, Wei; Chen, Ying-Chun; Chemical Science 13 (2022) 12433–12439; doi:10.1039/D2SC05210E

data_1567733
_publ_section_title
;
 Formal nucleophilic pyrrolylmethylation via palladium-based auto-tandem
 catalysis: switchable regiodivergent synthesis and remote chirality
 transfer
;
_journal_issue                   42
_journal_name_full               'Chemical Science'
_journal_page_first              12433
_journal_page_last               12439
_journal_paper_doi               10.1039/D2SC05210E
_journal_volume                  13
_journal_year                    2022
_chemical_formula_moiety         'C31 H30 N2 O4 S3'
_chemical_formula_sum            'C31 H30 N2 O4 S3'
_chemical_formula_weight         590.75
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-12-06
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-07-07 deposited with the CCDC.	2022-10-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 122.932(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   29.5374(19)
_cell_length_b                   9.7700(5)
_cell_length_c                   24.882(3)
_cell_measurement_reflns_used    7495
_cell_measurement_temperature    302.0
_cell_measurement_theta_max      23.087
_cell_measurement_theta_min      2.763
_cell_volume                     6026.7(9)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      302.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_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  0.0619
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            37923
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.496
_diffrn_reflns_theta_min         1.950
_diffrn_source_current           1.41
_diffrn_source_power             0.0705
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.284
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1059 before and 0.0593 after correction.
The Ratio of minimum to maximum transmission is 0.9375.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_description       block
_exptl_crystal_F_000             2480
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     378
_refine_ls_number_reflns         6899
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0920
_refine_ls_R_factor_gt           0.0497
_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/[\s^2^(Fo^2^)+(0.0568P)^2^+4.1428P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1164
_refine_ls_wR_factor_ref         0.1404
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4334
_reflns_number_total             6899
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc05210e2.cif
_cod_data_source_block           7o
_cod_depositor_comments
'Adding full bibliography for 1567732--1567733.cif.'
_cod_original_cell_volume        6026.6(8)
_cod_database_code               1567733
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.961
_shelx_estimated_absorpt_t_min   0.907
_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. Uiso/Uaniso restraints and constraints
Uanis(C2A) = Uanis(C2)
3. Others
 Sof(H01A)=Sof(S1A)=1-FVAR(1)
 Sof(H00Y)=Sof(S1)=FVAR(1)
 Sof(H00F)=Sof(C2A)=Sof(H2A)=1-FVAR(2)
 Sof(H012)=Sof(C2)=Sof(H2)=FVAR(2)
4.a Ternary CH refined with riding coordinates:
 C00G(H00G)
4.b Secondary CH2 refined with riding coordinates:
 C00O(H00A,H00B)
4.c Aromatic/amide H refined with riding coordinates:
 N008(H008), C00H(H00H), C00J(H00J), C00M(H00M), C00N(H00N), C00P(H00P),
 C00Q(H00Q), C00R(H00R), C00S(H00S), C00T(H00T), C00W(H00W), C00X(H00X),
 C00Y(H00Y), C00Y(H00F), C010(H010), C011(H011), C012(H012), C012(H01A),
 C013(H013), C2(H2), C2A(H2A)
4.d Idealised Me refined as rotating group:
 C00V(H00C,H00D,H00E), C00Z(H00I,H00K,H00L), C014(H01B,H01C,H01D)
;
_shelx_res_checksum              57797
_shelx_hkl_checksum              15891
_olex2_submission_special_instructions 'No special instructions were received'