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_1557972
_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_absolute_configuration S
_chemical_formula_moiety         'C26 H19 N O S'
_chemical_formula_sum            'C26 H19 N O S'
_chemical_formula_weight         393.48
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 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                 114.722(18)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.8666(13)
_cell_length_b                   9.9949(9)
_cell_length_c                   11.3565(17)
_cell_measurement_reflns_used    2284
_cell_measurement_temperature    298.0(2)
_cell_measurement_theta_max      31.9130
_cell_measurement_theta_min      3.0430
_cell_volume                     1017.3(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.7f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.7f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7f (Rigaku OD, 2015)'
_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      298.0(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.950
_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    -69.00 119.00   0.50   25.00    --   29.89  54.00-180.00  376
  2  \w    -69.00 119.00   0.50   25.00    --   29.89  54.00 -60.00  376
  3  \w    -69.00  23.00   0.50   25.00    --   29.89  54.00  60.00  184
;
_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      -0.0610215000
_diffrn_orient_matrix_UB_12      -0.0155063000
_diffrn_orient_matrix_UB_13      0.0152118000
_diffrn_orient_matrix_UB_21      -0.0379952000
_diffrn_orient_matrix_UB_22      -0.0297055000
_diffrn_orient_matrix_UB_23      -0.0619661000
_diffrn_orient_matrix_UB_31      0.0331403000
_diffrn_orient_matrix_UB_32      -0.0625346000
_diffrn_orient_matrix_UB_33      0.0256377000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_av_unetI/netI     0.0855
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12440
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.882
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.064
_diffrn_reflns_theta_min         2.838
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.176
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98321
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.7f (Rigaku Oxford Diffraction, 2015)
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    1.285
_exptl_crystal_description       plate
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 970 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         6810
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.1435
_refine_ls_R_factor_gt           0.0593
_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^)+(0.0389P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1060
_refine_ls_wR_factor_ref         0.1470
_reflns_Friedel_coverage         0.771
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.807
_reflns_number_gt                3217
_reflns_number_total             6810
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc01932a2.cif
_cod_data_source_block           sam_03_81_rt
_cod_depositor_comments
;Adding full bibliography for 1557972--1557973.cif.

 Adding full bibliography for 1557972--1557973.cif.
;
_cod_database_code               1557972
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C26 H14 N1 O1 S1'
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_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:
 C20(H20a,H20b)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C16(H16), C17(H17), C9(H9), C2(H2), C18(H18), C4(H4), C19(H19),
 C26(H26), C3(H3), C22(H22), C25(H25), C24(H24), C23(H23)
2.c Idealised Me refined as rotating group:
 C15(H15a,H15b,H15c)
;
_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 1.032
_oxdiff_exptl_absorpt_empirical_full_min 0.969