Palladium-catalyzed intramolecular transfer hydrogenation & cycloaddition of p-quinamine-tethered alkylidenecyclopropanes to synthesize perhydroindole scaffolds.
Cao, Bo; Wei, Yin; Shi, Min; Chemical communications (Cambridge, England) 54 (2018) 14085–14088; doi:10.1039/c8cc09041f

data_7122606
_publ_section_title
;
 Palladium-catalyzed intramolecular transfer hydrogenation &amp;
 cycloaddition of p-quinamine-tethered alkylidenecyclopropanes to
 synthesize perhydroindole scaffolds.
;
_journal_issue                   100
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              14085
_journal_page_last               14088
_journal_paper_doi               10.1039/c8cc09041f
_journal_volume                  54
_journal_year                    2018
_chemical_formula_sum            'C19 H23 N O3 S'
_chemical_formula_weight         345.44
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2018-04-03 deposited with the CCDC.
2018-11-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.424(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.0366(5)
_cell_length_b                   20.3622(13)
_cell_length_c                   12.3027(10)
_cell_measurement_reflns_used    4091
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      54.888
_cell_measurement_theta_min      5.207
_cell_volume                     1751.7(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8987
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.497
_diffrn_reflns_theta_min         3.080
_exptl_absorpt_coefficient_mu    0.201
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6464
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.854
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.066
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3215
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0860
_refine_ls_R_factor_gt           0.0725
_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^)+(0.1139P)^2^+2.3803P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2099
_refine_ls_wR_factor_ref         0.2223
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2565
_reflns_number_total             3215
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc09041f2.cif
_cod_data_source_block           mo_d8v18271_0m
_cod_depositor_comments
'Adding full bibliography for 7122605--7122606.cif.'
_cod_database_code               7122606
_shelx_estimated_absorpt_t_min   0.972
_shelx_estimated_absorpt_t_max   0.988
_shelxl_version_number           2013-4
_shelx_res_checksum              87583