Diphosphine-catalyzed mixed double-Michael reaction: a unified synthesis of indolines, dihydropyrrolopyridines, benzimidazolines, tetrahydroquinolines, tetrahydroisoquinolines, dihydrobenzo-1,4-oxazines, and dihydrobenzo-3,1-oxazines.
Sriramurthy, Vardhineedi; Kwon, Ohyun; Organic letters 12 (2010) 1084–1087; doi:10.1021/ol100078w

data_1502849
_publ_section_title
;
 Diphosphine-catalyzed mixed double-Michael reaction: a unified synthesis
 of indolines, dihydropyrrolopyridines, benzimidazolines,
 tetrahydroquinolines, tetrahydroisoquinolines, dihydrobenzo-1,4-oxazines,
 and dihydrobenzo-3,1-oxazines.
;
_journal_issue                   5
_journal_name_full               'Organic letters'
_journal_page_first              1084
_journal_page_last               1087
_journal_paper_doi               10.1021/ol100078w
_journal_volume                  12
_journal_year                    2010
_chemical_formula_moiety         'C18 H18 Br N O4 S'
_chemical_formula_sum            'C18 H18 Br N O4 S'
_chemical_formula_weight         424.30
_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                 109.796(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.474(3)
_cell_length_b                   22.890(7)
_cell_length_c                   7.794(3)
_cell_measurement_reflns_used    2814
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.16
_cell_measurement_theta_min      4.08
_cell_volume                     1758.2(10)
_computing_cell_refinement       'Bruker SMART APEX2'
_computing_data_collection       'Bruker SMART APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_av_sigmaI/netI    0.0537
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            17089
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         30.62
_diffrn_reflns_theta_min         3.85
_exptl_absorpt_coefficient_mu    2.480
_exptl_absorpt_correction_T_max  0.7896
_exptl_absorpt_correction_T_min  0.6134
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Bruker)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.603
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.755
_refine_diff_density_min         -1.170
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         5062
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.117
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0402
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0346P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0817
_refine_ls_wR_factor_ref         0.0918
_reflns_number_gt                3456
_reflns_number_total             5062
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol100078w_si_002.cif
_cod_data_source_block           kw2208sa
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1758.3(10)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1502849