Diastereoselective Synthesis of Structurally and Stereochemically Diversified 2-Oxa-7-azabicyclo[4.1.0]hept-3-enyl Carboxylates and Their Potential Application toward the Synthesis of Functionalized Pyranooxazolone and Pyrrole Derivatives through Skeletal Transformations.
Mukherjee, Prasun; Das, Asish R.; The Journal of organic chemistry 81 (2016) 5513–5524; doi:10.1021/acs.joc.6b00849

data_4032002
_publ_section_title
;
 Diastereoselective Synthesis of Structurally and Stereochemically
 Diversified 2-Oxa-7-azabicyclo[4.1.0]hept-3-enyl Carboxylates and Their
 Potential Application toward the Synthesis of Functionalized
 Pyranooxazolone and Pyrrole Derivatives through Skeletal Transformations.
;
_journal_issue                   13
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5513
_journal_page_last               5524
_journal_paper_doi               10.1021/acs.joc.6b00849
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C17 H16 N2 O3'
_chemical_formula_sum            'C17 H16 N2 O3'
_chemical_formula_weight         297.33
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 104.558(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.3945(6)
_cell_length_b                   14.2510(8)
_cell_length_c                   10.8994(5)
_cell_measurement_reflns_used    7597
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      31.00
_cell_measurement_theta_min      2.40
_cell_volume                     1562.71(15)
_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, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_sigmaI/netI    0.0369
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            28361
_diffrn_reflns_theta_full        37.99
_diffrn_reflns_theta_max         37.99
_diffrn_reflns_theta_min         1.93
_exptl_absorpt_coefficient_mu    0.088
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       granular
_exptl_crystal_F_000             628
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.4(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.830
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     399
_refine_ls_number_reflns         12513
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.830
_refine_ls_R_factor_all          0.0905
_refine_ls_R_factor_gt           0.0538
_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^)+(0.1646P)^2^+0.0154P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1613
_refine_ls_wR_factor_ref         0.2075
_reflns_number_gt                7884
_reflns_number_total             12513
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b00849_si_004.cif
_cod_data_source_block           ardpmptsa_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/current/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 4268 2015-11-12 08:31:59Z antanas 
;
_cod_original_cell_volume        1562.71(14)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4032002