Three-component reaction of 3-(diethoxyphosphoryl)coumarin, enolizable ketones and primary amines: Simple, stereoselective synthesis of benzo[1,3]oxazocine skeletons
Deredas, D.; Albrecht, Ł.; Maniukiewicz, W.; Wojciechowski, J.; Wolf, W. M.; Paluch, P.; Janecki, T.; Różalski, M.; Krajewska, U.; Janecka, A.; Krawczyk, H.; RSC Advances 3 (2013) 6821–; doi:10.1039/c3ra40184g

data_7238940
_publ_section_title
;
 Three-component reaction of 3-(diethoxyphosphoryl)coumarin, enolizable
 ketones and primary amines: Simple, stereoselective synthesis of
 benzo[1,3]oxazocine skeletons
;
_journal_issue                   19
_journal_name_full               'RSC Advances'
_journal_page_first              6821
_journal_paper_doi               10.1039/c3ra40184g
_journal_volume                  3
_journal_year                    2013
_chemical_formula_moiety         'C23 H28 N O5 P'
_chemical_formula_sum            'C23 H28 N O5 P'
_chemical_formula_weight         429.43
_chemical_melting_point          402(1)
_chemical_name_systematic
;
diethyl[(2S*,5S*,6S*)-3-benzyl-2-methyl-4-oxo-3,4,5,6-
tetrahydro-2H-2,6-methanobenzo[g][1,3]oxazocin-5-yl]phosphonate
;
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_audit_update_record
;
2012-11-23 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 94.728(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.1840(10)
_cell_length_b                   18.429(2)
_cell_length_c                   13.3004(15)
_cell_measurement_temperature    291(1)
_cell_volume                     2243.5(4)
_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      291(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0303
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            24377
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.89
_exptl_absorpt_coefficient_mu    0.156
_exptl_absorpt_correction_T_max  0.9426
_exptl_absorpt_correction_T_min  0.8810
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_description       prism
_exptl_crystal_F_000             912
_exptl_crystal_preparation
;
slow evaporation from acetone and n-heptane
;
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.045
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         3933
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0504
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0596P)^2^+1.6774P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1457
_refine_ls_wR_factor_ref         0.1496
_reflns_number_gt                3428
_reflns_number_total             3928
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ra40184g.txt
_cod_data_source_block           17
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7238940