Regiochemistry of the microwave-assisted reaction between aromatic amines and α-bromoketones to yield substituted 1H-indoles
Vara, Yosu; Aldaba, Eneko; Arrieta, Ana; Pizarro, José L.; Arriortua, María I.; Cossío, Fernando P.; Organic & Biomolecular Chemistry 6 (2008) 1763–1772; doi:10.1039/b719641e

data_7150872
_publ_section_title
;
 Regiochemistry of the microwave-assisted reaction between aromatic
 amines and \a-bromoketones to yield substituted 1H-indoles
;
_journal_issue                   10
_journal_name_full               'Organic &amp;  Biomolecular Chemistry'
_journal_page_first              1763
_journal_page_last               1772
_journal_paper_doi               10.1039/b719641e
_journal_volume                  6
_journal_year                    2008
_chemical_formula_sum            'C18 H19 N O4'
_chemical_formula_weight         313.34
_space_group_IT_number           14
_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_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             2005-03-30T17:09:05-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 100.855(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.5050(10)
_cell_length_b                   10.7366(7)
_cell_length_c                   10.6755(10)
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      31.8517
_cell_measurement_theta_min      3.134
_cell_volume                     1632.8(2)
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.24 beta (release 23.09.2004 CrysAlis171 .NET)
(compiled Sep 23 2004,08:58:26)
;
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.24 beta (release 23.09.2004 CrysAlis171 .NET)
(compiled Sep 23 2004,08:58:26)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.24 beta (release 23.09.2004 CrysAlis171 .NET)
(compiled Sep 23 2004,08:58:26)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.3504
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_orient_matrix_UB_11      -0.0226544536
_diffrn_orient_matrix_UB_12      0.0588227688
_diffrn_orient_matrix_UB_13      -0.0065694168
_diffrn_orient_matrix_UB_21      0.0443369295
_diffrn_orient_matrix_UB_22      0.0300453766
_diffrn_orient_matrix_UB_23      0.0102234536
_diffrn_orient_matrix_UB_31      -0.0004850723
_diffrn_orient_matrix_UB_32      -0.0011944617
_diffrn_orient_matrix_UB_33      -0.0665514037
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0449
_diffrn_reflns_av_unetI/netI     0.0478
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11596
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.43
_exptl_absorpt_coefficient_mu    0.09
_exptl_absorpt_correction_T_max  0.99431
_exptl_absorpt_correction_T_min  0.97472
_exptl_absorpt_correction_type   'numeric analytical'
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.24 beta (release 23.09.2004 CrysAlis171 .NET)
(compiled Sep 23 2004,08:58:26)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
;
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.20974
_exptl_crystal_size_mid          0.10778
_exptl_crystal_size_min          0.02684
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3308
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.134
_refine_ls_R_factor_all          0.1049
_refine_ls_R_factor_gt           0.0584
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0620P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1164
_refine_ls_wR_factor_ref         0.1363
_reflns_number_gt                2269
_reflns_number_total             3308
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b719641e.txt
_cod_data_source_block           fc9abs
_cod_depositor_comments
;

2018-03-14
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum        'C72 H76 N4 O16'
_cod_original_formula_units_Z    1
_cod_original_formula_weight     1253.37
_cod_database_code               7150872