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_1568280
_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         'C32 H27 N O3 S'
_chemical_formula_sum            'C32 H27 N O3 S'
_chemical_formula_weight         505.60
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2020-11-04
_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                 97.293(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.2549(3)
_cell_length_b                   11.5853(4)
_cell_length_c                   17.1735(4)
_cell_measurement_reflns_used    5266
_cell_measurement_temperature    294.93(10)
_cell_measurement_theta_max      71.5660
_cell_measurement_theta_min      3.8090
_cell_volume                     2615.86(12)
_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      294.93(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 0.977
_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    -53.00  31.00   1.00    1.00    --  -36.04  57.00 -90.00   84
  2  \w   -103.00 -19.00   1.00    1.00    --  -36.04 -57.00 150.00   84
  3  \w    -35.00  65.00   1.00    1.00    --   36.04 -19.00 -30.00  100
  4  \w      1.00  75.00   1.00    1.00    --   36.04 -99.00 -30.00   74
  5  \w     23.00  89.00   1.00    1.00    --   36.04-125.00 120.00   66
  6  \w     36.00 128.00   1.00    2.71    --  106.21 -30.00-180.00   92
  7  \w    100.00 176.00   1.00    2.71    --  106.21 111.00 -90.00   76
  8  \w     89.00 175.00   1.00    2.71    --  106.21  45.00   0.00   86
  9  \w     36.00 113.00   1.00    2.71    --  106.21-111.00 120.00   77
 10  \w     88.00 173.00   1.00    2.71    --  106.21  61.00 120.00   85
 11  \w     36.00 113.00   1.00    2.71    --  106.21-111.00  30.00   77
 12  \w     37.00 109.00   1.00    2.71    --  106.21 -94.00 -90.00   72
 13  \w     39.00 124.00   1.00    2.71    --  106.21 -61.00   0.00   85
 14  \w   -104.00  -9.00   1.00    1.00    --  -36.04 -77.00  60.00   95
 15  \w     19.00 103.00   1.00    1.00    --   36.04  57.00 -30.00   84
;
_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      -0.1040244000
_diffrn_orient_matrix_UB_12      -0.0609804000
_diffrn_orient_matrix_UB_13      -0.0064437000
_diffrn_orient_matrix_UB_21      0.0539454000
_diffrn_orient_matrix_UB_22      -0.1170062000
_diffrn_orient_matrix_UB_23      0.0157864000
_diffrn_orient_matrix_UB_31      -0.0020668000
_diffrn_orient_matrix_UB_32      0.0162096000
_diffrn_orient_matrix_UB_33      0.0888163000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14291
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.821
_diffrn_reflns_theta_min         3.978
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.368
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65750
_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    1.284
_exptl_crystal_description       block
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.451
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         5019
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0687
_refine_ls_R_factor_gt           0.0607
_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^)+(0.1151P)^2^+0.3217P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1639
_refine_ls_wR_factor_ref         0.1763
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4197
_reflns_number_total             5019
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc06813c2.cif
_cod_data_source_block           9
_cod_depositor_comments
'Adding full bibliography for 1568280--1568287.cif.'
_cod_database_code               1568280
_reflns_odcompleteness_completeness 99.96
_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:
 C00B(H00B), C00E(H00E)
2.b Secondary CH2 refined with riding coordinates:
 C00H(H00A,H00D)
2.c Aromatic/amide H refined with riding coordinates:
 C007(H007), C00C(H00C), C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L),
 C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P), C00R(H00R), C00S(H00S),
 C00T(H00T), C00U(H00U), C00V(H00V), C00W(H00W), C00X(H00X), C00Y(H00Y),
 C00Z(H00Z), C010(H010)
2.d Idealised Me refined as rotating group:
 C011(H01A,H01B,H01C)
;
_shelx_res_checksum              60995
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2020-11-04
_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 1.426
_oxdiff_exptl_absorpt_empirical_full_min 0.721