Construction of Multiple, Contiguous Quaternary Stereocenters in Acyclic Molecules by Lithiation-Borylation.
Watson, Charlotte G.; Balanta, Angelica; Elford, Tim G.; Essafi, Stéphanie; Harvey, Jeremy N.; Aggarwal, Varinder K.; Journal of the American Chemical Society  (2014) 141203101453003–; doi:10.1021/ja509029h

data_4123025
_publ_section_title
;
 Construction of Multiple, Contiguous Quaternary Stereocenters in Acyclic
 Molecules by Lithiation-Borylation.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              141203101453003
_journal_paper_doi               10.1021/ja509029h
_journal_year                    2014
_chemical_formula_moiety         'C21 H24 F3 N O'
_chemical_formula_sum            'C21 H24 F3 N O'
_chemical_formula_weight         363.41
_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
_atom_sites_solution_primary     iterative
_audit_creation_date             2014-06-25
_audit_creation_method
;
Olex2 1.2
(compiled 2014.06.23 svn.r2946 for OlexSys, GUI svn.r4855)
;
_cell_angle_alpha                90
_cell_angle_beta                 107.126(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.6822(2)
_cell_length_b                   13.2450(4)
_cell_length_c                   9.5272(3)
_cell_measurement_reflns_used    2603
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      26.62
_cell_measurement_theta_min      2.24
_cell_volume                     926.42(5)
_computing_cell_refinement       'SAINT v8.27A (Bruker, 2012)'
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2013)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Bruker Apex II kappa CCDC area detector'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7490
_diffrn_reflns_point_group_measured_fraction_full 0.926
_diffrn_reflns_point_group_measured_fraction_max 0.919
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.806
_diffrn_reflns_theta_min         2.237
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8804
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0618 before and 0.0400 after correction.
The Ratio of minimum to maximum transmission is 0.8804.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_description       plate
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 1295 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.1(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3643
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0349
_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^)+(0.0400P)^2^+0.1004P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0780
_refine_ls_wR_factor_ref         0.0817
_reflns_Friedel_coverage         0.760
_reflns_Friedel_fraction_full    0.846
_reflns_Friedel_fraction_max     0.830
_reflns_number_gt                3257
_reflns_number_total             3643
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja509029h_si_005.cif
_cod_data_source_block           testm1
_cod_database_code               4123025
_shelxl_version_number           2013-4
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C19(H19)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C18(H18A,H18B,H18C), C20(H20A,H20B,H20C), C21(H21A,H21B,
 H21C)
;
_shelx_res_checksum              76313
_shelx_hkl_checksum              77382
_olex2_submission_special_instructions 'No special instructions were received'