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_4123109
_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         '2(C H Cl3), C16 H24 N O, Cl'
_chemical_formula_sum            'C18 H26 Cl7 N O'
_chemical_formula_weight         520.55
_chemical_name_systematic
'2-methyl-9-phenyl-4-oxa-1-azaspiro[5.5]undecane chloride'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-10-23
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_cell_angle_alpha                103.245(2)
_cell_angle_beta                 94.106(2)
_cell_angle_gamma                110.337(2)
_cell_formula_units_Z            2
_cell_length_a                   9.0230(8)
_cell_length_b                   10.7212(10)
_cell_length_c                   13.9030(13)
_cell_measurement_reflns_used    7245
_cell_measurement_temperature    223.2(2)
_cell_measurement_theta_max      30.15
_cell_measurement_theta_min      2.44
_cell_volume                     1210.59(19)
_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      223.2(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 0.997
_diffrn_measurement_device       'kappa-stage diffractometer'
_diffrn_measurement_device_type  'Bruker Kappa Apex2 Duo'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'focusing graphite'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            23944
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.593
_diffrn_reflns_theta_min         2.105
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.830
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.7097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0400 before and 0.0356 after correction.
The Ratio of minimum to maximum transmission is 0.9512.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_description       needle
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.871
_refine_diff_density_min         -0.734
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         7418
_refine_ls_number_restraints     279
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0487
_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^)+(0.0571P)^2^+0.7100P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1239
_refine_ls_wR_factor_ref         0.1347
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5740
_reflns_number_total             7418
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja511232b_si_003.cif
_cod_data_source_block           mo_jb221014_0m
_cod_database_code               4123109
_shelxl_version_number           2014/6
_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
 Cl2-C17 \\sim Cl3-C17 \\sim Cl1-C17 \\sim Cl2S-C1A \\sim Cl01-C1A \\sim
Cl3S-C1A
 with sigma of 0.02
3. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(Cl3)=Sof(H17A)=Sof(Cl1A)=Sof(Cl2A)=1-FVAR(1)
 Sof(Cl1)=Sof(Cl2)=Sof(H17)=Sof(Cl3A)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C4(H4), C15(H15), C17(H17), C17(H17A), C1A(H1A)
6.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C6(H6A,H6B), C8(H8A,H8B), C10(H10A,H10B), C12(H12A,H12B),
 C13(H13A,H13B), N14(H14A,H14B)
6.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C11(H11), C18(H18), C19(H19)
6.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_shelx_res_checksum              14003
_shelx_hkl_checksum              97354
_olex2_exptl_crystal_mounting_method
'Crystals burst at temperatures lower than 220K.'
_olex2_submission_original_sample_id jb221014
_olex2_submission_special_instructions 'No special instructions were received'