Diastereodivergent <i>cis</i>- and <i>trans</i>-fused [4 + 2] annulations of cyclic 1,3-dienes and 1-azadienes <i>via</i> ligand-controlled palladium catalysis.
Hu, Yuan; Huang, Jin-Yu; Yan, Ru-Jie; Chen, Zhi-Chao; Ouyang, Qin; Du, Wei; Chen, Ying-Chun; Chemical science 14 (2023) 1896–1901; doi:10.1039/d2sc06813c

data_1568287
_publ_section_title
;
 Diastereodivergent <i>cis</i>- and <i>trans</i>-fused [4 + 2] annulations
 of cyclic 1,3-dienes and 1-azadienes <i>via</i> ligand-controlled
 palladium catalysis.
;
_journal_issue                   7
_journal_name_full               'Chemical science'
_journal_page_first              1896
_journal_page_last               1901
_journal_paper_doi               10.1039/d2sc06813c
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C28 H25 N O3 S'
_chemical_formula_sum            'C28 H25 N O3 S'
_chemical_formula_weight         455.55
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_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             2020-11-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-12-17 deposited with the CCDC.	2023-01-16 downloaded from the CCDC.
;
_cell_angle_alpha                92.051(3)
_cell_angle_beta                 93.362(3)
_cell_angle_gamma                94.406(3)
_cell_formula_units_Z            4
_cell_length_a                   11.6139(7)
_cell_length_b                   13.4764(10)
_cell_length_c                   14.9925(10)
_cell_measurement_reflns_used    8699
_cell_measurement_temperature    290
_cell_measurement_theta_max      20.565
_cell_measurement_theta_min      2.414
_cell_volume                     2333.7(3)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 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      290.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_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  0.1297
_diffrn_reflns_av_unetI/netI     0.1036
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            85300
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.549
_diffrn_reflns_theta_min         1.997
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.169
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6927
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0942 before and 0.0658 after correction. The Ratio of minimum to maximum transmission is 0.9291. 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    1.297
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     597
_refine_ls_number_reflns         10757
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.1390
_refine_ls_R_factor_gt           0.0603
_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^)+(0.0288P)^2^+0.8674P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1328
_refine_ls_wR_factor_ref         0.1605
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5467
_reflns_number_total             10757
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc06813c2.cif
_cod_data_source_block           12
_cod_depositor_comments
'Adding full bibliography for 1568280--1568287.cif.'
_cod_database_code               1568287
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.967
_shelx_estimated_absorpt_t_min   0.951
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00A(H00A), C00F(H00F), C00L(H00L), C00N(H00N), C00X(H00X), C00Y(H00Y)
2.b Secondary CH2 refined with riding coordinates:
 C014(H01J,H01K), C01B(H01M,H01O), C01C(H01A,H01B), C01I(H01C,H01D)
2.c Aromatic/amide H refined with riding coordinates:
 C00Q(H00Q), C00R(H00R), C00S(H00S), C00U(H00U), C00V(H00V), C00W(H00W),
 C00Z(H00Z), C010(H010), C011(H011), C012(H012), C013(H013), C015(H015),
 C016(H016), C017(H017), C018(H018), C019(H019), C01A(H01L), C01D(H01P),
 C01F(H01Q), C01G(H01G), C01H(H01H), C01J(H01T), C01K(H01U), C01L(H01V),
 C01M(H01W), C01N(H01N), C01O(H01X), C01P(H01Y), C01R(H01R), C01S(H01S)
2.d Idealised Me refined as rotating group:
 C01T(H01E,H01F,H01I), C01U(H01Z,H,HA)
;
_olex2_submission_special_instructions 'No special instructions were received'