Palladium-catalysed 5-endo-trig allylic (hetero)arylation
Singh, Bara; Bankar, Siddheshwar K.; Kumar, Ketan; Ramasastry, S. S. V.; Chemical Science 11 (2020) 4948–4953; doi:10.1039/D0SC01932A

data_1557973
_publ_section_title
;
 Palladium-catalysed 5-endo-trig allylic (hetero)arylation
;
_journal_issue                   19
_journal_name_full               'Chemical Science'
_journal_page_first              4948
_journal_page_last               4953
_journal_paper_doi               10.1039/D0SC01932A
_journal_volume                  11
_journal_year                    2020
_chemical_formula_moiety         'C18 H20 S'
_chemical_formula_sum            'C18 H20 S'
_chemical_formula_weight         268.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-11-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-11-13 deposited with the CCDC.	2020-04-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.646(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.0379(13)
_cell_length_b                   9.5393(9)
_cell_length_c                   16.2242(19)
_cell_measurement_reflns_used    1209
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.8790
_cell_measurement_theta_min      2.8670
_cell_volume                     1503.1(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_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      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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     55.00  82.00   0.50   20.00    --   29.89  54.00-150.00   54
  2  \w     35.00  62.00   0.50   20.00    --   29.89  54.00 150.00   54
  3  \w    -65.00 119.00   0.50   20.00    --   29.89  54.00  30.00  368
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0174177000
_diffrn_orient_matrix_UB_12      -0.0699828000
_diffrn_orient_matrix_UB_13      -0.0132301000
_diffrn_orient_matrix_UB_21      -0.0636976000
_diffrn_orient_matrix_UB_22      0.0071290000
_diffrn_orient_matrix_UB_23      0.0110870000
_diffrn_orient_matrix_UB_31      -0.0315146000
_diffrn_orient_matrix_UB_32      0.0238313000
_diffrn_orient_matrix_UB_33      -0.0417411000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_av_unetI/netI     0.0719
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5289
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         2.498
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.200
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.28278
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.186
_exptl_crystal_F_000             576
_refine_diff_density_max         1.078
_refine_diff_density_min         -0.505
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2636
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.1534
_refine_ls_R_factor_gt           0.1084
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2911
_refine_ls_wR_factor_ref         0.3453
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1545
_reflns_number_total             2636
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc01932a2.cif
_cod_data_source_block           sb08sbc
_cod_depositor_comments
;Adding full bibliography for 1557972--1557973.cif.

 Adding full bibliography for 1557972--1557973.cif.
;
_cod_database_code               1557973
_shelx_shelxl_version_number     2017/1
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.97
_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 Secondary CH2 refined with riding coordinates:
 C00D(H00E,H00F), C00G(H00I,H00J), C00J(H00Q,H00R)
2.b Aromatic/amide H refined with riding coordinates:
 C008(H008), C009(H009), C00C(H00D), C00E(H00G), C00F(H00H)
2.c Idealised Me refined as rotating group:
 C00A(H00A,H00B,H00C), C00H(H00K,H00L,H00M), C00I(H00N,H00O,H00P)
;
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 2.440
_oxdiff_exptl_absorpt_empirical_full_min 0.539