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_4123027
_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         'C29 H32 F3 N O2'
_chemical_formula_sum            'C29 H32 F3 N O2'
_chemical_formula_weight         483.55
_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             2014-07-16
_audit_creation_method
;
Olex2 1.2
(compiled 2014.06.27 svn.r2953 for OlexSys, GUI svn.r4855)
;
_cell_angle_alpha                90
_cell_angle_beta                 101.604(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.9876(3)
_cell_length_b                   10.1713(3)
_cell_length_c                   12.4643(4)
_cell_measurement_reflns_used    3789
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      26.74
_cell_measurement_theta_min      2.39
_cell_volume                     1240.33(7)
_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 0.998
_diffrn_measurement_device       'Bruker Apex II kappa CCDC area detector'
_diffrn_measurement_device_type  'Bruker Apex II kappa CCDC area detector'
_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  0.0233
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10235
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.851
_diffrn_reflns_theta_min         1.668
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6484
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0480 before and 0.0393 after correction.
The Ratio of minimum to maximum transmission is 0.8699.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_description       plate
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 1950 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.3(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     348
_refine_ls_number_reflns         5193
_refine_ls_number_restraints     34
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0343
_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^)+(0.0353P)^2^+0.1749P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0737
_refine_ls_wR_factor_ref         0.0773
_reflns_Friedel_coverage         0.841
_reflns_Friedel_fraction_full    0.959
_reflns_Friedel_fraction_max     0.942
_reflns_number_gt                4650
_reflns_number_total             5193
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja509029h_si_007.cif
_cod_data_source_block           testm1
_cod_database_code               4123027
_shelxl_version_number           2013-4
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 F1-C10 \\sim F1A-C10 \\sim F2-C10 \\sim F2A-C10 \\sim F3-C10 \\sim F3A-C10
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
F1 \\sim F1A \\sim F2 \\sim F2A \\sim F3 \\sim F3A: within 1.7A with sigma of
0.003 and sigma for terminal atoms of 0.006
4. Others
 Fixed Sof: F1(0.5737) F2(0.5737) F3(0.5737) F3A(0.4263) F1A(0.4263) F2A(0.4263)
5.a Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B)
5.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C28(H28), C18(H18), C27(H27), C25(H25), C3(H3), C14(H14), C2(H2),
 C24(H24), C16(H16), C6(H6), C5(H5), C4(H4), C15(H15), C17(H17)
5.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C12(H12A,H12B,H12C), C20(H20A,H20B,H20C), C29(H29A,H29B,
 H29C), C8(H8A,H8B,H8C)
;
_shelx_res_checksum              15318
_shelx_hkl_checksum              87513
_olex2_submission_special_instructions 'No special instructions were received'