Cycloalkene Carbonitriles in Rhodium-Catalyzed 1,4-Addition and Formal Synthesis of Vabicaserin.
Dziechciejewski, Wojciech J.; Weber, Regina; Sowada, Oliver; Boysen, Mike M. K.; Organic letters 17 (2015) 4132–4135; doi:10.1021/acs.orglett.5b01849

data_1529402
_publ_section_title
;
 Cycloalkene Carbonitriles in Rhodium-Catalyzed 1,4-Addition and Formal
 Synthesis of Vabicaserin.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              4132
_journal_page_last               4135
_journal_paper_doi               10.1021/acs.orglett.5b01849
_journal_volume                  17
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_sum            'C19 H20 Br N O'
_chemical_formula_weight         358.27
_chemical_name_common            wd154
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 90.133(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.2250(4)
_cell_length_b                   13.4400(11)
_cell_length_c                   11.8487(10)
_cell_measurement_reflns_used    9709
_cell_measurement_temperature    200.(2)
_cell_measurement_theta_max      27.5051
_cell_measurement_theta_min      2.2869
_cell_volume                     832.06(12)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      200.(2)
_diffrn_detector_area_resol_mean 8.3330
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART X2S'
_diffrn_measurement_method       '\f and \w scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0574
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15539
_diffrn_reflns_theta_full        25.06
_diffrn_reflns_theta_max         25.06
_diffrn_reflns_theta_min         2.29
_exptl_absorpt_coefficient_mu    2.472
_exptl_absorpt_correction_T_max  0.64
_exptl_absorpt_correction_T_min  0.35
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/2 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.550
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.572
_refine_diff_density_min         -0.342
_refine_ls_abs_structure_details
'Classical Flack method preferred over Parsons because s.u. lower.'
_refine_ls_abs_structure_Flack   0.001(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2948
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0464
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0962P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1197
_refine_ls_wR_factor_ref         0.1215
_reflns_number_gt                2801
_reflns_number_total             2948
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b01849_si_002.cif
_cod_data_source_block           I
_cod_depositor_comments          'Adding full bibliography for 1529402.cif.'
_cod_database_code               1529402