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_7238947
_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_absolute_configuration rmad
_chemical_formula_moiety         '2(C27 H34 N O5 P)'
_chemical_formula_sum            'C54 H68 N2 O10 P2'
_chemical_formula_weight         967.0861
_chemical_melting_point          492(1)
_chemical_name_systematic
;
diethyl [(3S,4S)-4-(2-hydroxyphenyl)-2-oxo-1-((S)-1-
phenylethyl)-1,2,3,4,5,6,7,8-octahydroquinolin-3-yl]phosphonate
;
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21 1'
_cell_angle_alpha                90.00
_cell_angle_beta                 101.437(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   15.3297(2)
_cell_length_b                   9.0879(1)
_cell_length_c                   19.0093(3)
_cell_measurement_temperature    291(1)
_cell_volume                     2595.69(6)
_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 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0209
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            29421
_diffrn_reflns_theta_full        66.53
_diffrn_reflns_theta_max         66.53
_diffrn_reflns_theta_min         2.37
_exptl_absorpt_coefficient_mu    1.236
_exptl_absorpt_correction_T_max  0.7932
_exptl_absorpt_correction_T_min  0.6430
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_description       prism
_exptl_crystal_F_000             1032
_exptl_crystal_preparation
;
slow evaporation for benzene and n-heptane 3:1 mixture
;
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.002(13)
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_matrix_type           full
_refine_ls_number_parameters     681
_refine_ls_number_reflns         8887
_refine_ls_number_restraints     31
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0342
_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^)+(0.0625P)^2^+0.3497P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0957
_refine_ls_wR_factor_ref         0.0964
_reflns_number_gt                8719
_reflns_number_total             8887
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ra40184g.txt
_cod_data_source_block           44
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7238947