Ru(II)-catalyzed allenylation and sequential annulation of <i>N</i>-tosylbenzamides with propargyl alcohols.
Kumar, Shreemoyee; Nair, Akshay M.; Volla, Chandra M. R.; Chemical communications (Cambridge, England) 57 (2021) 6280–6283; doi:10.1039/d1cc01768c

data_7128390
_publ_section_title
;
 Ru(II)-catalyzed allenylation and sequential annulation of
 <i>N</i>-tosylbenzamides with propargyl alcohols.
;
_journal_issue                   51
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              6280
_journal_page_last               6283
_journal_paper_doi               10.1039/d1cc01768c
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C31 H27 N O4 S'
_chemical_formula_sum            'C31 H27 N O4 S'
_chemical_formula_weight         509.59
_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
_audit_creation_date             2020-08-25
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2021-03-23 deposited with the CCDC.	2021-05-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.367(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.2727(6)
_cell_length_b                   9.0999(4)
_cell_length_c                   20.3049(10)
_cell_measurement_reflns_used    10696
_cell_measurement_temperature    150
_cell_measurement_theta_max      30.6240
_cell_measurement_theta_min      2.0560
_cell_volume                     2585.5(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (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_temperature      150.0
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -78.00  25.00   1.00    8.00    --  -20.00   0.00 -36.00  103
  2  \w    -50.00  70.00   1.00    8.00    --  -20.00  72.00 -36.00  120
  3  \w    -54.00  -4.00   1.00    8.00    --  -20.00  72.00-108.00   50
  4  \w    -60.00 -30.00   1.00    8.00    --  -20.00 -72.00-180.00   30
  5  \w   -110.00  70.00   1.00    8.00    --  -20.00   0.00-108.00  180
  6  \w    -72.00 -18.00   1.00    8.00    --  -20.00 -72.00-108.00   54
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0259304000
_diffrn_orient_matrix_UB_12      -0.0254447000
_diffrn_orient_matrix_UB_13      0.0241704000
_diffrn_orient_matrix_UB_21      -0.0066461000
_diffrn_orient_matrix_UB_22      -0.0689520000
_diffrn_orient_matrix_UB_23      -0.0165439000
_diffrn_orient_matrix_UB_31      0.0430645000
_diffrn_orient_matrix_UB_32      -0.0259786000
_diffrn_orient_matrix_UB_33      0.0202653000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0893
_diffrn_reflns_av_unetI/netI     0.0587
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            25583
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.265
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.163
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46253
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_description       block
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.205
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.041
_refine_diff_density_max         0.422
_refine_diff_density_min         -0.493
_refine_diff_density_rms         0.094
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         4557
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0731
_refine_ls_R_factor_gt           0.0498
_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^)+(0.0505P)^2^+1.6822P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1114
_refine_ls_wR_factor_ref         0.1313
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3497
_reflns_number_total             4557
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc01768c2.cif
_cod_data_source_block           cmrv-sh-ph_mo
_cod_depositor_comments          'Adding full bibliography for 7128390.cif.'
_cod_database_code               7128390
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.967
_reflns_odcompleteness_completeness 92.43
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.11
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C13(H13), C4(H4), C3(H3), C17(H17), C7(H7), C30(H30), C12(H12),
 C11(H11), C6(H6), C31(H31), C29(H29), C27(H27), C18(H18), C20(H20), C21(H21),
 C28(H28), C19(H19)
2.b Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C24(H24A,H24B,H24C), C1(H1A,H1B,H1C)
;
_shelx_res_checksum              23454
_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 1.427
_oxdiff_exptl_absorpt_empirical_full_min 0.744