Synthesis of Azepines via a [6 + 1] Annulation of Ynenitriles with Reformatsky Reagents.
Yoshimatsu, Mitsuhiro; Tanaka, Miki; Fujimura, Yu; Ito, Yukiteru; Goto, Yusuke; Kobayashi, Yuka; Wasada, Hiroaki; Hatae, Noriyuki; Tanabe, Genzoh; Muraoka, Osamu; The Journal of organic chemistry 80 (2015) 9480–9494; doi:10.1021/acs.joc.5b01397

data_4036280
_publ_section_title
;
 Synthesis of Azepines via a [6 + 1] Annulation of Ynenitriles with
 Reformatsky Reagents.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9480
_journal_page_last               9494
_journal_paper_doi               10.1021/acs.joc.5b01397
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C22 H24 N2 O4 S2 '
_chemical_formula_sum            'C22 H24 N2 O4 S2'
_chemical_formula_weight         444.56
_chemical_melting_point          460.6(5)
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      61
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_audit_creation_date             2003-12-07
_audit_creation_method           'by CrystalStructure 3.8'
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            8
_cell_length_a                   8.0665(5)
_cell_length_b                   16.2776(8)
_cell_length_c                   32.7774(16)
_cell_measurement_reflns_used    23053
_cell_measurement_temperature    296.1
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_cell_volume                     4303.8(4)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.8'
_computing_structure_refinement  SHELXL
_computing_structure_solution    SIR97
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.094
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            38784
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_exptl_absorpt_coefficient_mu    0.279
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_correction_T_min  0.643
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1872.00
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.89
_refine_diff_density_min         -0.44
_refine_ls_extinction_coef       0.0018(4)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4935
_refine_ls_R_factor_gt           0.0680
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0768P)^2^+6.2912P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1880
_reflns_number_gt                3597
_reflns_number_total             4935
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            jo5b01397_si_002.cif
_cod_data_source_block           General
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '187-188 degree' was
changed to '460.6(5)' -- it was converted from degrees Celsius(C) to
Kelvins(K), the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_formula_sum        'C22 H24 N2 O4 S2 '
_cod_database_code               4036280