One-Step Synthesis of Saturated Spirocyclic N-Heterocycles with Stannyl Amine Protocol (SnAP) Reagents and Ketones.
Siau, Woon-Yew; Bode, Jeffrey W.; Journal of the American Chemical Society  (2014) 141209160958008–; doi:10.1021/ja511232b

data_4123110
_publ_section_title
;
 One-Step Synthesis of Saturated Spirocyclic N-Heterocycles with Stannyl
 Amine Protocol (SnAP) Reagents and Ketones.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              141209160958008
_journal_paper_doi               10.1021/ja511232b
_journal_year                    2014
_chemical_formula_moiety         'C14 H23 N O'
_chemical_formula_sum            'C14 H23 N O'
_chemical_formula_weight         221.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2014-07-31
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_cell_angle_alpha                90
_cell_angle_beta                 123.760(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.9447(18)
_cell_length_b                   20.027(2)
_cell_length_c                   10.2082(13)
_cell_measurement_reflns_used    8538
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      30.53
_cell_measurement_theta_min      3.15
_cell_volume                     2370.1(5)
_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 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'kappa-stage diffractometer'
_diffrn_measurement_device_type  'Bruker/Nonius Kappa Apex2'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            26374
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.582
_diffrn_reflns_theta_min         2.030
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.7176
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0928 before and 0.0421 after correction.
The Ratio of minimum to maximum transmission is 0.9618.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_description       plate
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.427
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         3625
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0382
_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^)+(0.0570P)^2^+1.1243P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1026
_refine_ls_wR_factor_ref         0.1109
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3012
_reflns_number_total             3625
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja511232b_si_002.cif
_cod_data_source_block           jb290714_0m
_cod_database_code               4123110
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.971
_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
 N1-H1
 0.91 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C2(H2), C4(H4), C6(H6), C11(H11), C13(H13)
3.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C5(H5A,H5B), C7(H7A,H7B), C8(H8A,H8B), C10(H10A,H10B), C12(H12A,
 H12B), C14(H14A,H14B)
3.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_olex2_submission_original_sample_id jb290714
_olex2_submission_special_instructions 'No special instructions were received'