Remarkable effect of N-substituent on enantioselective ruthenium-catalyzed propargylation of indoles with propargylic alcohols.
Matsuzawa, Hiroshi; Kanao, Keiichiro; Miyake, Yoshihiro; Nishibayashi, Yoshiaki; Organic letters 9 (2007) 5561–5564; doi:10.1021/ol7025203

data_1505661
_publ_section_title
;
 Remarkable effect of N-substituent on enantioselective
 ruthenium-catalyzed propargylation of indoles with propargylic alcohols.
;
_journal_issue                   26
_journal_name_full               'Organic letters'
_journal_page_first              5561
_journal_page_last               5564
_journal_paper_doi               10.1021/ol7025203
_journal_volume                  9
_journal_year                    2007
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C27 H18 Cl N '
_chemical_formula_sum            'C27 H18 Cl N'
_chemical_formula_weight         391.90
_chemical_melting_point          143.9(4)
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   5.8810(9)
_cell_length_b                   9.0184(15)
_cell_length_c                   36.938(9)
_cell_measurement_reflns_used    4484
_cell_measurement_temperature    103.1
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.2
_cell_volume                     1959.1(7)
_computing_cell_refinement       CrystalClear
_computing_data_collection       CrystalClear
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.8'
_computing_structure_refinement  CRYSTALS
_computing_structure_solution    SIR97
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.040
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            11326
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_exptl_absorpt_coefficient_mu    0.208
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_correction_T_min  0.846
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            pale_Yellow
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             816.00
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.56
_refine_diff_density_min         -0.66
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  1844 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.00(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     284
_refine_ls_number_reflns         4460
_refine_ls_R_factor_gt           0.0503
_refine_ls_shift/su_max          0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w = 1/[1.3600\s(Fo^2^)]/(4Fo^2^)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0892
_reflns_number_gt                3211
_reflns_number_total             4460
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ol7025203-file003.cif
_cod_data_source_block           '_C27H18NCl'
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '143.5-144.3' was changed to
'143.9(4)' - the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_formula_sum        'C27 H18 Cl N '
_cod_database_code               1505661