Ruthenium(II)-Catalyzed Regioselective-Controlled Allenylation/Cyclization of Benzimides with Propargyl Alcohols.
Anukumar, Adapa; Tamizmani, Masilamani; Jeganmohan, Masilamani; The Journal of organic chemistry 83 (2018) 8567–8580; doi:10.1021/acs.joc.8b01123

data_4035611
_publ_section_title
;
 Ruthenium(II)-Catalyzed Regioselective-Controlled
 Allenylation/Cyclization of Benzimides with Propargyl Alcohols.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8567
_journal_page_last               8580
_journal_paper_doi               10.1021/acs.joc.8b01123
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C21 H23 N O'
_chemical_formula_sum            'C21 H23 N O'
_chemical_formula_weight         305.42
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_atom_sites_solution_primary     direct
_audit_creation_date             2018-01-22
_audit_creation_method
;
Olex2 1.2
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370)
;
_cell_angle_alpha                90.661(2)
_cell_angle_beta                 93.685(2)
_cell_angle_gamma                98.549(2)
_cell_formula_units_Z            2
_cell_length_a                   7.8808(4)
_cell_length_b                   10.2314(5)
_cell_length_c                   11.1564(5)
_cell_measurement_reflns_used    5462
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.53
_cell_measurement_theta_min      2.62
_cell_volume                     887.52(7)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.9975
_diffrn_measured_fraction_theta_max 0.9975
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1527
_diffrn_reflns_av_unetI/netI     0.0733
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            14398
_diffrn_reflns_theta_full        24.9985
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.01
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.1428
_exptl_crystal_description       Rectangular
_exptl_crystal_F_000             328.1341
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.3328
_refine_diff_density_min         -0.3032
_refine_diff_density_rms         0.0589
_refine_ls_d_res_high            0.8409
_refine_ls_d_res_low             10.1154
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0955
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    37
_refine_ls_number_parameters     213
_refine_ls_number_reflns         3132
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0955
_refine_ls_R_factor_all          0.0805
_refine_ls_R_factor_gt           0.0647
_refine_ls_shift/su_max          0.0029
_refine_ls_shift/su_mean         0.0005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1092P)^2^+0.0521P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1737
_refine_ls_wR_factor_ref         0.1974
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              12
_reflns_limit_k_min              -12
_reflns_limit_l_max              13
_reflns_limit_l_min              0
_reflns_number_gt                2314
_reflns_number_total             3132
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            jo8b01123_si_002.cif
_cod_data_source_block           127
_cod_database_code               4035611
_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:
 C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C20(H20a,H20b)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16)
2.d Idealised Me refined as rotating group:
 C10(H10a,H10b,H10c), C18(H18a,H18b,H18c), C19(H19a,H19b,H19c), C21(H21a,H21b,
 H21c)
;
_olex2_submission_special_instructions 'No special instructions were received'