Electroreductive intermolecular coupling of 3-methoxycarbonylindoles with ketones.
Kise, Naoki; Sueyoshi, Akinori; Takeuchi, Shin-Ichirou; Sakurai, Toshihiko; Organic letters 15 (2013) 2746–2749; doi:10.1021/ol4010799

data_1512092
_publ_section_title
;
 Electroreductive intermolecular coupling of 3-methoxycarbonylindoles with
 ketones.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2746
_journal_page_last               2749
_journal_paper_doi               10.1021/ol4010799
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C16 H21 N O3'
_chemical_formula_sum            'C16 H21 N O3'
_chemical_formula_weight         275.34
_chemical_melting_point          367.5(5)
_chemical_name_systematic
; 
(2R*,3R*)-methyl 2-(1-hydroxycyclopentyl)-1-methylindoline-3-carboxylate 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.808(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.696(3)
_cell_length_b                   15.927(6)
_cell_length_c                   17.750(7)
_cell_measurement_temperature    298(2)
_cell_volume                     3022.3(19)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        PROCESS-AUTO
_computing_publication_material  yadokari-XG
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0684
_diffrn_reflns_av_sigmaI/netI    0.0592
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            23450
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.94
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9836
_exptl_absorpt_correction_T_min  0.9596
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     367
_refine_ls_number_reflns         6651
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.989
_refine_ls_R_factor_all          0.0976
_refine_ls_R_factor_gt           0.0590
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1017P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1563
_refine_ls_wR_factor_ref         0.1740
_reflns_number_gt                4051
_reflns_number_total             6651
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol4010799_si_004.cif
_cod_data_source_block           trans-6b
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '367-368' was changed to '367.5(5)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        3022.3(18)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1512092