Evolution of Natural Product Scaffolds by Acyl- and Arylnitroso Hetero-Diels-Alder Reactions: New Chemistry on Piperine
Viktor Krchňák; Katherine R. Waring; Bruce C. Noll; Ute Moellmann; Hans-Martin Dahse; Marvin J. Miller; Journal of Organic Chemistry 73 (2008) 4559–4567; doi:10.1021/jo8004827

data_4023477
_publ_section_title
;
 Evolution of Natural Product Scaffolds by Acyl- and Arylnitroso
 Hetero-Diels-Alder Reactions: New Chemistry on Piperine
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4559
_journal_page_last               4567
_journal_paper_doi               10.1021/jo8004827
_journal_volume                  73
_journal_year                    2008
_chemical_compound_source        synthesized
_chemical_formula_moiety         'C23 H26 N3 O3, C2 F3 O2'
_chemical_formula_sum            'C25 H26 F3 N3 O5'
_chemical_formula_weight         505.49
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                79.199(3)
_cell_angle_beta                 70.316(3)
_cell_angle_gamma                77.971(3)
_cell_formula_units_Z            2
_cell_length_a                   9.7374(6)
_cell_length_b                   10.9885(7)
_cell_length_c                   11.9183(8)
_cell_measurement_reflns_used    9956
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.311
_cell_measurement_theta_min      2.420
_cell_volume                     1164.82(13)
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2007; Sheldrick, 2008)'
_computing_molecular_graphics    'XP (Sheldrick, 2008)'
_computing_publication_material  'XCIF (Sheldrick, 2008)/enCIFer (CCDC, 2005)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker X8-Apex II CCD diffractometer'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_sigmaI/netI    0.0259
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            34427
_diffrn_reflns_theta_full        27.85
_diffrn_reflns_theta_max         27.85
_diffrn_reflns_theta_min         1.83
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Siemens KFFMO2K-90'
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.96
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Sheldrick, G. M. (2007). SADABS. University of G\"ottingen, Germany.'
_exptl_crystal_colour            'clear colorless'
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             528
_exptl_crystal_recrystallization_method
'vapor diffusion of hexanes into CDCl~3~/CH~2~Cl~2~ solution'
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     330
_refine_ls_number_reflns         5440
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0480
_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^)+(0.0549P)^2^+0.9095P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1201
_refine_ls_wR_factor_ref         0.1361
_reflns_number_gt                3973
_reflns_number_total             5440
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8004827-File001.cif
_cod_data_source_block           bcn348_0m
_cod_database_code               4023477