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_7238944
_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         '4(C23 H23 N O2), C4 H10 O'
_chemical_formula_sum            'C96 H102 N4 O9'
_chemical_formula_weight         1455.88
_chemical_melting_point          387(1)
_chemical_name_systematic
;
(3aS,9S,9aS)-10-methylene-12-[(R)-1-phenylethyl]-2,3,9,9a-tetrahydro-1H-3a,9-
-(epiminoethano)cyclopenta[b]chromen-11-one
;
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_cell_angle_alpha                99.392(1)
_cell_angle_beta                 91.714(1)
_cell_angle_gamma                90.912(1)
_cell_formula_units_Z            1
_cell_length_a                   9.2805(1)
_cell_length_b                   12.9476(2)
_cell_length_c                   16.1252(2)
_cell_measurement_temperature    100(1)
_cell_volume                     1910.35(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      100(2)
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_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  0.0232
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            62988
_diffrn_reflns_theta_full        68.00
_diffrn_reflns_theta_max         70.41
_diffrn_reflns_theta_min         2.78
_exptl_absorpt_coefficient_mu    0.635
_exptl_absorpt_correction_T_max  0.9392
_exptl_absorpt_correction_T_min  0.8324
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_description       plate
_exptl_crystal_F_000             778
_exptl_crystal_preparation
;
slow evaporation from diethyl ether solution
;
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.134
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881 for 6958 Fridel pairs'
_refine_ls_abs_structure_Flack   -0.07(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_matrix_type           full
_refine_ls_number_parameters     989
_refine_ls_number_reflns         12999
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0257
_refine_ls_R_factor_gt           0.0256
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0465P)^2^+0.3153P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0741
_refine_ls_wR_factor_ref         0.0755
_reflns_number_gt                12996
_reflns_number_total             12999
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ra40184g.txt
_cod_data_source_block           33
_cod_database_code               7238944