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_1568283
_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_absolute_configuration ad
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2020-11-30
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2020-12-17 deposited with the CCDC.	2023-01-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.0546(3)
_cell_length_b                   11.54205(18)
_cell_length_c                   18.2492(4)
_cell_measurement_reflns_used    5009
_cell_measurement_temperature    292.90(10)
_cell_measurement_theta_max      71.2530
_cell_measurement_theta_min      3.8010
_cell_volume                     2328.47(9)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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_environment      air
_diffrn_ambient_temperature      292.90(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -73.00  37.00   1.00    1.47    --  -34.98  19.00  90.00  110
  2  \w      1.00  75.00   1.00    1.47    --   34.98 -99.00 -60.00   74
  3  \w     23.00  90.00   1.00    1.47    --   34.98-125.00-150.00   67
  4  \w    -33.00  53.00   1.00    1.47    --   34.98 -57.00-150.00   86
  5  \w     23.00  90.00   1.00    1.47    --   34.98-125.00  90.00   67
  6  \w      1.00  75.00   1.00    1.47    --   34.98 -99.00  90.00   74
  7  \w     23.00  90.00   1.00    1.47    --   34.98-125.00-180.00   67
  8  \w     78.00 176.00   1.00    5.86    --  106.90  77.00 -30.00   98
  9  \w     78.00 176.00   1.00    5.86    --  106.90  77.00   0.00   98
 10  \w     37.00 127.00   1.00    5.86    --  106.90 -45.00 -60.00   90
 11  \w     36.00 113.00   1.00    5.86    --  106.90-111.00 150.00   77
 12  \w    100.00 178.00   1.00    5.86    --  106.90 111.00  30.00   78
 13  \w     37.00 110.00   1.00    5.86    --  106.90 -94.00  60.00   73
 14  \w     79.00 176.00   1.00    5.86    --  106.90  75.00  83.00   97
 15  \w    100.00 178.00   1.00    5.86    --  106.90 111.00   0.00   78
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0886218000
_diffrn_orient_matrix_UB_12      0.1027709000
_diffrn_orient_matrix_UB_13      0.0039665000
_diffrn_orient_matrix_UB_21      0.0419617000
_diffrn_orient_matrix_UB_22      0.0405116000
_diffrn_orient_matrix_UB_23      -0.0763186000
_diffrn_orient_matrix_UB_31      -0.0990380000
_diffrn_orient_matrix_UB_32      -0.0749523000
_diffrn_orient_matrix_UB_33      -0.0358208000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12665
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.424
_diffrn_reflns_theta_min         4.533
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.475
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71566
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.299
_exptl_crystal_description       plate
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Flack x determined using 1604 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.011(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4476
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0564
_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^)+(0.1138P)^2^+0.0354P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1522
_refine_ls_wR_factor_ref         0.1590
_reflns_Friedel_coverage         0.746
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.976
_reflns_number_gt                4118
_reflns_number_total             4476
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc06813c2.cif
_cod_data_source_block           13
_cod_depositor_comments
'Adding full bibliography for 1568280--1568287.cif.'
_cod_original_cell_volume        2328.47(8)
_cod_database_code               1568283
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C006(H006), C007(H007), C00B(H00B)
2.b Secondary CH2 refined with riding coordinates:
 C00I(H00A,H00C), C00S(H00D,H00E)
2.c Aromatic/amide H refined with riding coordinates:
 C00F(H00F), C00H(H00H), C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M),
 C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R), C00T(H00T),
 C00U(H00U), C00V(H00V), C00W(H00W)
2.d Idealised Me refined as rotating group:
 C00X(H00G,H00I,H00S)
;
_shelx_res_checksum              36971
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2020-11-30
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.490
_oxdiff_exptl_absorpt_empirical_full_min 0.777