Short Approach toward the Nonracemic A,B,E Tricyclic Core of Calyciphylline B-Type Alkaloids.
Boissarie, Patrick; Bélanger, Guillaume; Organic letters  (2017) –; doi:10.1021/acs.orglett.7b01566

data_1546439
_publ_section_title
;
 Short Approach toward the Nonracemic A,B,E Tricyclic Core of
 Calyciphylline B-Type Alkaloids.
;
_journal_name_full               'Organic letters'
_journal_paper_doi               10.1021/acs.orglett.7b01566
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C20 H20 N2 O7'
_chemical_formula_sum            'C20 H20 N2 O7'
_chemical_formula_weight         400.38
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2017-04-05T08:10:15-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 96.477(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.1034(8)
_cell_length_b                   6.1744(4)
_cell_length_c                   14.0512(10)
_cell_measurement_reflns_used    7188
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      70.7277
_cell_measurement_theta_min      3.1653
_cell_measurement_wavelength     1.54186
_cell_volume                     957.16(12)
_computing_cell_refinement       'SAINT V8.34A integration software'
_computing_data_collection       'Bruker APEX2 software'
_computing_data_reduction        'SORTAV (Blessing, 1995)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector                 'APEX-II CCD'
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       '\f or \w oscillation scans'
_diffrn_orient_matrix_type       'x-axis to radiation source'
_diffrn_orient_matrix_UB_11      0.845005E-1
_diffrn_orient_matrix_UB_12      -0.559319E-1
_diffrn_orient_matrix_UB_13      -0.143349E-3
_diffrn_orient_matrix_UB_21      -0.988957E-2
_diffrn_orient_matrix_UB_22      0.256926E-2
_diffrn_orient_matrix_UB_23      -0.716157E-1
_diffrn_orient_matrix_UB_31      0.312667E-1
_diffrn_orient_matrix_UB_32      0.151972
_diffrn_orient_matrix_UB_33      0.115798E-2
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54186
_diffrn_reflns_av_R_equivalents  0.0552
_diffrn_reflns_av_unetI/netI     0.0857
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5106
_diffrn_reflns_reduction_process
;
 Scaled and merged with Sortav
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
_diffrn_reflns_theta_full        70
_diffrn_reflns_theta_max         71.06
_diffrn_reflns_theta_min         4.82
_diffrn_source                   'sealed x-ray tube'
_exptl_absorpt_coefficient_mu    0.895
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_correction_T_min  0.489
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.06
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.958
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         3064
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.958
_refine_ls_R_factor_all          0.063
_refine_ls_R_factor_gt           0.0486
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0833P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1235
_refine_ls_wR_factor_ref         0.1365
_reflns_number_gt                2530
_reflns_number_total             3064
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            ol7b01566_si_002.cif
_cod_data_source_block           cu_belanger_pb6115f1_0m
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1546439