Copper(I)-Catalyzed Cascade Sulfonimidate to Sulfonamide Rearrangement: Synthesis of Imidazo[1,2-a][1,4]diazepin-7(6H)-one
Muthupandi Nagaraj; Muthusamy Boominathan; Devanathan Perumal; Shanmugam Muthusubramanian; Nattamai Bhuvanesh; Journal of Organic Chemistry 77 (2012) 6319–6326; doi:10.1021/jo300855f

data_4027301
_publ_section_title
;
 Copper(I)-Catalyzed Cascade Sulfonimidate to Sulfonamide Rearrangement:
 Synthesis of Imidazo[1,2-a][1,4]diazepin-7(6H)-one
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6319
_journal_page_last               6326
_journal_paper_doi               10.1021/jo300855f
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C20 H19 N3 O3 S'
_chemical_formula_weight         381.44
_chemical_melting_point          470(1)
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 103.418(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.1261(8)
_cell_length_b                   28.654(4)
_cell_length_c                   10.7204(16)
_cell_measurement_reflns_used    982
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      62.34
_cell_measurement_theta_min      4.51
_cell_volume                     1830.5(4)
_computing_cell_refinement
;
CELL-NOW (Sheldrick, 2003) and SAINT (BRUKER-NONIUS, 2003)
;
_computing_data_collection       'FRAMBO (BRUKER-NONIUS, 2003)'
_computing_data_reduction        'Bruker APEX2'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'BRUKER GADDS D8 Discover'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1194
_diffrn_reflns_av_sigmaI/netI    0.0554
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            29169
_diffrn_reflns_theta_full        59.98
_diffrn_reflns_theta_max         59.98
_diffrn_reflns_theta_min         5.25
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.794
_exptl_absorpt_correction_T_max  0.8698
_exptl_absorpt_correction_T_min  0.6830
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; (Sheldrick, 2006)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.496
_refine_diff_density_min         -0.968
_refine_diff_density_rms         0.151
_refine_ls_extinction_coef       0.056(3)
_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   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         2682
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0731
_refine_ls_R_factor_gt           0.0677
_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^)+(0.1160P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1553
_refine_ls_wR_factor_ref         0.1595
_reflns_number_gt                2266
_reflns_number_total             2682
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo300855f_si_002_1.cif
_cod_data_source_block           mes
_cod_database_code               4027301