Synthesis of 2,3-Dihydro-1H-2-benzazepin-1-ones and 3H-2-Benzoxepin-1-ones by Isocyanide-Based Multicomponent Reaction/Wittig Sequence Starting from Phosphonium Salt Precursors.
Wang, Long; Ren, Zhi-Lin; Ding, Ming-Wu; The Journal of organic chemistry 80 (2014) 641–; doi:10.1021/jo502275f

data_4030330
_publ_section_title
;
 Synthesis of 2,3-Dihydro-1H-2-benzazepin-1-ones and
 3H-2-Benzoxepin-1-ones by Isocyanide-Based Multicomponent Reaction/Wittig
 Sequence Starting from Phosphonium Salt Precursors.
;
_journal_issue                   1
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              641
_journal_paper_doi               10.1021/jo502275f
_journal_volume                  80
_journal_year                    2014
_chemical_formula_moiety         'C21 H20 Cl N O3'
_chemical_formula_sum            'C21 H20 Cl N O3'
_chemical_formula_weight         369.83
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   20.8235(4)
_cell_length_b                   7.24050(10)
_cell_length_c                   24.6478(4)
_cell_measurement_reflns_used    6212
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      52.66
_cell_measurement_theta_min      3.59
_cell_volume                     3716.21(11)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker 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      296(2)
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w 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  0.0227
_diffrn_reflns_av_sigmaI/netI    0.0211
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            11864
_diffrn_reflns_theta_full        52.81
_diffrn_reflns_theta_max         52.81
_diffrn_reflns_theta_min         3.59
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.986
_exptl_absorpt_correction_T_max  0.9072
_exptl_absorpt_correction_T_min  0.8161
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Sheldrick,1997'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1552
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         2090
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.119
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0341
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0445P)^2^+1.3472P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0897
_refine_ls_wR_factor_ref         0.0913
_reflns_number_gt                1977
_reflns_number_total             2090
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo502275f_si_001.cif
_cod_data_source_block           t
_cod_depositor_comments
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The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/COD-crude-data--automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2935 2014-11-11 08:27:57Z andrius 

 Adding full bibliography for 4030330.cif.
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_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               4030330