In Situ Generation of a Regio- and Diastereoselective Hydroaminoalkylation Catalyst Using Commercially Available Starting Materials.
Edwards, Peter M.; Schafer, Laurel L.; Organic letters 19 (2017) 5720–5723; doi:10.1021/acs.orglett.7b02149

data_1547727
_publ_section_title
;
 In Situ Generation of a Regio- and Diastereoselective
 Hydroaminoalkylation Catalyst Using Commercially Available Starting
 Materials.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              5720
_journal_page_last               5723
_journal_paper_doi               10.1021/acs.orglett.7b02149
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'Cl, C15 H24 N O'
_chemical_formula_sum            'C15 H24 Cl N O'
_chemical_formula_weight         269.80
_chemical_name_systematic
'1-(4-methoxyphenyl)-2,3,6-trimethylpiperidin-1-ium chloride'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-04-20
_audit_creation_method
;
Olex2 1.2
(compiled 2014.02.28 svn.r2899 for OlexSys, GUI svn.r4781)
;
_cell_angle_alpha                90.00(3)
_cell_angle_beta                 90.00(3)
_cell_angle_gamma                90.00(3)
_cell_formula_units_Z            8
_cell_length_a                   21.142(4)
_cell_length_b                   9.442(2)
_cell_length_c                   14.826(3)
_cell_measurement_reflns_used    873
_cell_measurement_temperature    100
_cell_measurement_theta_max      19.68
_cell_measurement_theta_min      2.37
_cell_volume                     2959.6(10)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    'ShelXT (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.525
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0597
_diffrn_reflns_av_unetI/netI     0.0703
_diffrn_reflns_Laue_measured_fraction_full 0.525
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5300
_diffrn_reflns_point_group_measured_fraction_full 0.425
_diffrn_reflns_point_group_measured_fraction_max 0.813
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         19.914
_diffrn_reflns_theta_min         2.362
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.248
_exptl_absorpt_correction_T_max  0.7444
_exptl_absorpt_correction_T_min  0.6625
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
? was used for absorption correction.
wR2(int) was 0.0759 before and 0.0610 after correction.
The Ratio of minimum to maximum transmission is 0.8900.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_description       prism
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.047
_exptl_crystal_size_min          0.035
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 601 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     333
_refine_ls_number_reflns         2220
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.981
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0354
_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^)+(0.0233P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0676
_refine_ls_wR_factor_ref         0.0730
_reflns_Friedel_coverage         0.555
_reflns_Friedel_fraction_full    0.317
_reflns_Friedel_fraction_max     0.612
_reflns_number_gt                1869
_reflns_number_total             2220
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b02149_si_001.cif
_cod_data_source_block           ls709_0m_a
_cod_depositor_comments
;
Adding full bibliography for 1547726--1547727.cif.

2019-03-26
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_cell_volume        2959.7(10)
_cod_original_formula_moiety     '8(Cl), 8(C15 H24 N O)'
_cod_original_formula_sum        'C120 H192 Cl8 N8 O8'
_cod_original_formula_units_Z    1
_cod_original_formula_weight     2158.40
_cod_database_code               1547727
_shelxl_version_number           2014-1
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.959
_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
 N2-H2 = N1-H1
 1 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 N1(H1), N2(H2), C22(H22), C28(H28), C26(H26), C8(H8), C13(H13), C11(H11)
3.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C24(H24A,H24B), C00V(H00A,H00B), C25(H25A,H25B)
3.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C20(H20), C18(H18), C3(H3), C17(H17), C19(H19), C6(H6)
3.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C29(H29A,H29B,H29C), C23(H23A,H23B,H23C), C27(H27A,H27B,
 H27C), C9(H9A,H9B,H9C), C14(H14A,H14B,H14C), C12(H12A,H12B,H12C), C1(H1A,H1B,
 H1C)
;
_olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2008)'
_olex2_submission_special_instructions 'No special instructions were received'