Solvent- and Catalyst-Free Synthesis of Nitrogen-Containing Bicycles through Hemiaminal Formation/Diastereoselective Hetero-Diels-Alder Reaction with Diazenes.
Crouillebois, Laurence; Pantaine, Loïc; Marrot, Jérôme; Coeffard, Vincent; Moreau, Xavier; Greck, Christine; The Journal of organic chemistry 80 (2014) 595–; doi:10.1021/jo502087a

data_4030323
_publ_section_title
;
 Solvent- and Catalyst-Free Synthesis of Nitrogen-Containing Bicycles
 through Hemiaminal Formation/Diastereoselective Hetero-Diels-Alder
 Reaction with Diazenes.
;
_journal_issue                   1
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              595
_journal_paper_doi               10.1021/jo502087a
_journal_volume                  80
_journal_year                    2014
_chemical_formula_sum            'C19 H25 N3 O4'
_chemical_formula_weight         359.42
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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            4
_cell_length_a                   6.9301(5)
_cell_length_b                   15.6506(12)
_cell_length_c                   22.8010(18)
_cell_measurement_reflns_used    9860
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      22.12
_cell_measurement_theta_min      2.21
_cell_volume                     2473.0(3)
_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      297(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0852
_diffrn_reflns_av_sigmaI/netI    0.0516
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            107991
_diffrn_reflns_theta_full        30.05
_diffrn_reflns_theta_max         30.05
_diffrn_reflns_theta_min         1.58
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  0.9945
_exptl_absorpt_correction_T_min  0.9798
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, V2.10)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    0.965
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         7213
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.1195
_refine_ls_R_factor_gt           0.0872
_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^)+(0.1606P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2445
_refine_ls_wR_factor_ref         0.2656
_reflns_number_gt                4661
_reflns_number_total             7213
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo502087a_si_002.cif
_cod_data_source_block           1
_cod_depositor_comments
;
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 4030323.cif.
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               4030323