Catalytic enantioselective cyclization/cross-coupling with alkyl electrophiles.
Cong, Huan; Fu, Gregory C.; Journal of the American Chemical Society 136 (2014) 3788–3791; doi:10.1021/ja500706v

data_4121455
_publ_section_title
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 Catalytic enantioselective cyclization/cross-coupling with alkyl
 electrophiles.
;
_journal_issue                   10
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3788
_journal_page_last               3791
_journal_paper_doi               10.1021/ja500706v
_journal_volume                  136
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H23 N O3'
_chemical_formula_sum            'C22 H23 N O3'
_chemical_formula_weight         349.41
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-01-21
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.95310(10)
_cell_length_b                   12.3326(3)
_cell_length_c                   29.4659(7)
_cell_measurement_reflns_used    9941
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      71.496
_cell_measurement_theta_min      2.999
_cell_volume                     1799.91(7)
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      120.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_unetI/netI     0.0118
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            31273
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         71.513
_diffrn_reflns_theta_min         2.999
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.684
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9407
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0451 before and 0.0347 after correction.
The Ratio of minimum to maximum transmission is 0.9407.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.147
_exptl_crystal_size_mid          0.142
_exptl_crystal_size_min          0.071
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.128
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details
;
 Flack x determined using 1391 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.04(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3492
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0249
_refine_ls_R_factor_gt           0.0244
_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^)+(0.0327P)^2^+0.2965P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0617
_refine_ls_wR_factor_ref         0.0627
_reflns_Friedel_coverage         0.683
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                3442
_reflns_number_total             3492
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja500706v_si_001.cif
_cod_data_source_block           crystal001
_cod_database_code               4121455
_shelxl_version_number           2013-2
_shelx_estimated_absorpt_t_max   0.953
_shelx_estimated_absorpt_t_min   0.906
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C17(H17), C18(H18), C19(H19), C20(H20)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;