Broadly Applicable Stereoselective Syntheses of Serrulatane, Amphilectane Diterpenes, and Their Diastereoisomeric Congeners Using Asymmetric Hydrovinylation for Absolute Stereochemical Control.
Tenneti, Srinivasarao; Biswas, Souvagya; Cox, Glen Adam; Mans, Daniel J.; Lim, Hwan Jung; RajanBabu, T. V.; Journal of the American Chemical Society 140 (2018) 9868–9881; doi:10.1021/jacs.8b03549

data_4132379
_publ_section_title
;
 Broadly Applicable Stereoselective Syntheses of Serrulatane, Amphilectane
 Diterpenes, and Their Diastereoisomeric Congeners Using Asymmetric
 Hydrovinylation for Absolute Stereochemical Control.
;
_journal_issue                   31
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9868
_journal_page_last               9881
_journal_paper_doi               10.1021/jacs.8b03549
_journal_volume                  140
_journal_year                    2018
_chemical_absolute_configuration rmad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C31 H31 Br1 N1 Ni1 O2 P1'
_chemical_formula_sum            'C31 H31 Br N Ni O2 P'
_chemical_formula_weight         619.16
_chemical_name_common            'RajanBabu 1617'
_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_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             2010-08-09T16:14:06-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 110.383(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.2162(1)
_cell_length_b                   18.1432(2)
_cell_length_c                   9.8241(1)
_cell_measurement_reflns_used    3245
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      2.037
_cell_measurement_wavelength     0.71073
_cell_volume                     1372.76(4)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_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, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'phi and omega scans''
_diffrn_orient_matrix_type       'by Nonius Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      -0.115271
_diffrn_orient_matrix_UB_12      -0.195977E-1
_diffrn_orient_matrix_UB_13      -0.633239E-1
_diffrn_orient_matrix_UB_21      -0.115629E-1
_diffrn_orient_matrix_UB_22      0.416502E-1
_diffrn_orient_matrix_UB_23      -0.694171E-1
_diffrn_orient_matrix_UB_31      0.586298E-1
_diffrn_orient_matrix_UB_32      -0.303164E-1
_diffrn_orient_matrix_UB_33      -0.544338E-1
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.052
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            25363
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.21
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    2.25
_exptl_absorpt_correction_T_max  0.763
_exptl_absorpt_correction_T_min  0.623
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'HKL Scalepack (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'rectangular plate'
_exptl_crystal_F_000             636
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.565
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.004(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     356
_refine_ls_number_reflns         6207
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.028
_refine_ls_R_factor_gt           0.0237
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0258P)^2^+0.2329P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0523
_refine_ls_wR_factor_ref         0.0538
_reflns_number_gt                5766
_reflns_number_total             6207
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja8b03549_si_002.cif
_cod_data_source_block           shelxl
_cod_original_cell_volume        1372.76(3)
_cod_original_sg_symbol_H-M      P21
_cod_database_code               4132379