Catalytic Direct Acetoxylation of Indoles
Ilga Mutule; Edgars Suna; Kristofer Olofsson; Benjamin Pelcman; Journal of Organic Chemistry 74 (2009) 7195–7198; doi:10.1021/jo901321b

data_4024849
_publ_contact_author_name        I.Mutule
_publ_section_title
;
Catalytic Direct Acetoxylation of Indoles
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7195
_journal_page_last               7198
_journal_paper_doi               10.1021/jo901321b
_journal_volume                  74
_journal_year                    2009
_chemical_compound_source        'Local laboratory'
_chemical_formula_moiety         'C22 H18 Br2 N2 O5 '
_chemical_formula_sum            'C22 H18 Br2 N2 O5'
_chemical_formula_weight         550.203
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           maXus
_cell_angle_alpha                90.00
_cell_angle_beta                 117.4887(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.5637(2)
_cell_length_b                   19.8815(6)
_cell_length_c                   11.3971(3)
_cell_measurement_reflns_used    11367
_cell_measurement_temperature    293
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     2123.41(9)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       KappaCCD
_computing_data_reduction        'Denzo and Scalepak (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'Ortep (Johnson, 1976)'
_computing_publication_material  'maXus(Mackay et al., 1999)'
_computing_structure_refinement  'maXus(Mackay et al., 1999)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       KappaCCD
_diffrn_measurement_method       CCD
_diffrn_orient_matrix_type       X=UH
_diffrn_orient_matrix_UB_11      -0.07984
_diffrn_orient_matrix_UB_12      0.03141
_diffrn_orient_matrix_UB_13      -0.06346
_diffrn_orient_matrix_UB_21      0.03336
_diffrn_orient_matrix_UB_22      0.01555
_diffrn_orient_matrix_UB_23      -0.03428
_diffrn_orient_matrix_UB_31      -0.03563
_diffrn_orient_matrix_UB_32      -0.06591
_diffrn_orient_matrix_UB_33      -0.06457
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           ' MoK\a'
_diffrn_radiation_wavelength_id  all
_diffrn_reflns_av_R_equivalents  0.031
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8023
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.02
_exptl_absorpt_coefficient_mu    3.85
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Brown
_exptl_crystal_density_diffrn    1.721
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Prism (0.11x0.12x0.16 mm)'
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.54
_refine_diff_density_min         -0.52
_refine_diff_density_rms         0.20
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.924
_refine_ls_goodness_of_fit_gt    1.706
_refine_ls_goodness_of_fit_ref   1.693
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    18
_refine_ls_number_parameters     289
_refine_ls_number_reflns         3015
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.091
_refine_ls_R_factor_gt           0.042
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef F^2^
_refine_ls_weighting_details     ' w = 1 / ( s^2^(Fo^2^) + 0.10000 * Fo^2^)'
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_all         0.117
_refine_ls_wR_factor_gt          0.071
_refine_ls_wR_factor_ref         0.071
_reflns_d_resolution_high        0.62
_reflns_d_resolution_low         2.16
_reflns_limit_h_max              13
_reflns_limit_h_min              0
_reflns_limit_k_max              25
_reflns_limit_k_min              0
_reflns_limit_l_max              13
_reflns_limit_l_min              -14
_reflns_number_gt                3025
_reflns_number_total             4868
_reflns_threshold_expression     'I> 3.00 sigma(I)'
_cod_data_source_file            jo901321b_si_002.cif
_cod_data_source_block           global
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_atom_site_adp_type' tag value 'Uij' was replaced with 'Uani' value
31 time.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_atom_sites_solution_hydrogens' value 'geom, diff' was changed to
'mixed'.

Automatic conversion script
Id: cif_fix_values 6452 2018-10-05 10:23:21Z andrius 
;
_cod_original_sg_symbol_H-M      'P 21/c        '
_cod_original_formula_sum        'C22 H18 Br2 N2 O5 '
_cod_database_code               4024849