SnAP-eX Reagents for the Synthesis of Exocyclic 3-Amino- and 3-Alkoxypyrrolidines and Piperidines from Aldehydes.
Luescher, Michael U.; Bode, Jeffrey W.; Organic letters 18 (2016) 2652–2655; doi:10.1021/acs.orglett.6b01099

data_1555569
_publ_section_title
;
 SnAP-eX Reagents for the Synthesis of Exocyclic 3-Amino- and
 3-Alkoxypyrrolidines and Piperidines from Aldehydes.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2652
_journal_page_last               2655
_journal_paper_doi               10.1021/acs.orglett.6b01099
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C13 H15 F5 N O2, Cl'
_chemical_formula_sum            'C13 H15 Cl F5 N O2'
_chemical_formula_weight         347.71
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2016-03-30
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 109.128(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.8400(17)
_cell_length_b                   6.9273(7)
_cell_length_c                   15.2459(18)
_cell_measurement_reflns_used    6003
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      2.34
_cell_volume                     1480.8(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 8.33
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'kappa-stage diffractometer'
_diffrn_measurement_device_type  'Bruker/Nonius Kappa Apex2'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'double mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            19547
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.528
_diffrn_reflns_theta_min         2.828
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms high brilliance'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.318
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6515
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0757 before and 0.0469 after correction.
The Ratio of minimum to maximum transmission is 0.8738.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.560
_exptl_crystal_description       plate
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         3395
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0345
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0401P)^2^+0.7730P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0805
_refine_ls_wR_factor_ref         0.0890
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2737
_reflns_number_total             3395
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b01099_si_003.cif
_cod_data_source_block           jb240316_1_1_0m
_cod_database_code               1555569
_shelx_estimated_absorpt_t_max   0.987
_shelx_estimated_absorpt_t_min   0.948
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N1-H1B = N1-H1A
 0.91 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C3(H3), C7(H7)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B)
3.c Idealised Me refined as rotating group:
 C1(H1C,H1D,H1E)
;
_shelx_res_checksum              60013
_shelx_hkl_checksum              26325
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-03-24
_olex2_date_sample_submission    2016-03-22
_olex2_submission_original_sample_id jb240316_1_1
_olex2_submission_special_instructions 'No special instructions were received'