C-2/C-3 Annulation and C-2 Alkylation of Indoles with 2-Alkoxycyclopropanoate Esters
Barbora Bajtos; Ming Yu; Hongda Zhao; Brian L. Pagenkopf; Journal of the American Chemical Society 129 (2007) 9631–9634; doi:10.1021/ja067821+

data_4111333
_publ_section_title
;
 C-2/C-3 Annulation and C-2 Alkylation of Indoles with
 2-Alkoxycyclopropanoate Esters
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9631
_journal_page_last               9634
_journal_paper_doi               10.1021/ja067821+
_journal_volume                  129
_journal_year                    2007
_chemical_formula_sum            'C17 H20 I N O3'
_chemical_formula_weight         413.24
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 95.172(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.3471(5)
_cell_length_b                   5.4389(2)
_cell_length_c                   12.4747(5)
_cell_measurement_temperature    153(2)
_cell_volume                     834.32(6)
_computing_cell_refinement       'Collect software, Nonius B.V. 1998'
_computing_data_collection       'Collect software, Nonius B.V. 1998'
_computing_data_reduction
;
DENZO and Scalepack (Otwinoski and Minor, 1997)
;
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_structure_refinement  'XL SHELXTL/PC, Siemens Analytical'
_computing_structure_solution
;

SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., 
Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R.
;
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       \w-scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0440
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3673
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         3.28
_exptl_absorpt_coefficient_mu    1.931
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.52
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Scalepack
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.645
_exptl_crystal_description       lathes
_exptl_crystal_F_000             412
_exptl_crystal_size_max          1.07
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.439
_refine_diff_density_min         -1.171
_refine_diff_density_rms         0.133
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_extinction_coef       0.0144(19)
_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   1.156
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         3673
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.156
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0457
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0509P)^2^+1.4642P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1086
_refine_ls_wR_factor_ref         0.1138
_reflns_number_gt                3333
_reflns_number_total             3673
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja067821si20070529_084334.cif
_cod_data_source_block           ym1821
_cod_database_code               4111333