Synthesis of Amino-Substituted Indanes and Tetralins via Consecutive Multibond-Forming Tandem Processes
Mark W. Grafton; Louis J. Farrugia; Andrew Sutherland; Journal of Organic Chemistry 78 (2013) 7199–7207; doi:10.1021/jo401182r

data_4028442
_publ_section_title
;
 Synthesis of Amino-Substituted Indanes and Tetralins via Consecutive
 Multibond-Forming Tandem Processes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7199
_journal_page_last               7207
_journal_paper_doi               10.1021/jo401182r
_journal_volume                  78
_journal_year                    2013
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C20 H20 Cl3 N O3'
_chemical_formula_sum            'C20 H20 Cl3 N O3'
_chemical_formula_weight         428.72
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.2
_audit_creation_date             2013-03-04T10:09:28-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                73.870(2)
_cell_angle_beta                 78.263(2)
_cell_angle_gamma                77.712(2)
_cell_formula_units_Z            4
_cell_length_a                   9.5784(4)
_cell_length_b                   12.4773(5)
_cell_length_c                   17.9818(8)
_cell_measurement_reflns_used    9715
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.95
_cell_measurement_theta_min      2.32
_cell_measurement_wavelength     0.71073
_cell_volume                     1993.18(15)
_computing_cell_refinement       'SAINT V8.27B integration software'
_computing_data_collection       'Bruker APEX2 software'
_computing_data_reduction        'SORTAV (Blessing, 1995)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'APEX-II CCD'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       '\f or \w oscillation scans'
_diffrn_orient_matrix_UB_11      0.020632
_diffrn_orient_matrix_UB_12      -0.040889
_diffrn_orient_matrix_UB_13      0.053932
_diffrn_orient_matrix_UB_21      -0.061177
_diffrn_orient_matrix_UB_22      -0.056631
_diffrn_orient_matrix_UB_23      0.001753
_diffrn_orient_matrix_UB_31      0.086746
_diffrn_orient_matrix_UB_32      -0.047741
_diffrn_orient_matrix_UB_33      -0.022818
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.066
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            100988
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_reduction_process
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.998
_diffrn_reflns_theta_min         1.193
_diffrn_source                   'sealed x-ray tube'
_exptl_absorpt_coefficient_mu    0.48
_exptl_absorpt_correction_T_max  0.744
_exptl_absorpt_correction_T_min  0.68
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_description       irregular
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         1.35
_refine_diff_density_min         -0.632
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    refU
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     539
_refine_ls_number_reflns         11347
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0697
_refine_ls_R_factor_gt           0.0544
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0854P)^2^+1.2806P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.146
_refine_ls_wR_factor_ref         0.1541
_reflns_number_gt                9088
_reflns_number_total             11347
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo401182r_si_002.cif
_cod_data_source_block           shelx
_cod_database_code               4028442