Bespoke SnAP reagents for the synthesis of C-substituted spirocyclic and bicyclic saturated N-heterocycles.
Geoghegan, Kimberly; Bode, Jeffrey W.; Organic letters 17 (2015) 1934–1937; doi:10.1021/acs.orglett.5b00618

data_1554917
_publ_section_title
;
 Bespoke SnAP reagents for the synthesis of C-substituted spirocyclic and
 bicyclic saturated N-heterocycles.
;
_journal_issue                   8
_journal_name_full               'Organic letters'
_journal_page_first              1934
_journal_page_last               1937
_journal_paper_doi               10.1021/acs.orglett.5b00618
_journal_volume                  17
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H16 F3 N O'
_chemical_formula_sum            'C18 H16 F3 N O'
_chemical_formula_weight         319.32
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2014-08-22
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   5.8836(4)
_cell_length_b                   19.2027(12)
_cell_length_c                   26.5181(16)
_cell_measurement_reflns_used    4030
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      50.43
_cell_measurement_theta_min      2.84
_cell_volume                     2996.0(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 0.594
_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  'double mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0586
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_Laue_measured_fraction_full 0.594
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            17512
_diffrn_reflns_point_group_measured_fraction_full 0.578
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         50.495
_diffrn_reflns_theta_min         2.841
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.961
_exptl_absorpt_correction_T_max  0.7500
_exptl_absorpt_correction_T_min  0.6665
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0744 before and 0.0492 after correction. The Ratio of minimum to maximum transmission is 0.8887. 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    1.416
_exptl_crystal_description       needle
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.035
_exptl_crystal_size_min          0.015
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 1042 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     421
_refine_ls_number_reflns         3122
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0355
_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^)+(0.0536P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0773
_refine_ls_wR_factor_ref         0.0821
_reflns_Friedel_coverage         0.684
_reflns_Friedel_fraction_full    0.557
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                2727
_reflns_number_total             3122
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b00618_si_004.cif
_cod_data_source_block           cu_w210814_0m
_cod_database_code               1554917
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.986
_shelx_estimated_absorpt_t_min   0.893
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H14A,H14B} of C14, {H16A,H16B} of C16, {H34A,H34B} of C34,
   {H36A,H36B} of C36
 At 1.5 times of:
  {H1,H2A} of C36
2. Restrained distances
 N1-H1
 0.91 with sigma of 0.02
 N2-H2A
 0.91 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C5(H5), C6(H6), C15(H15), C24(H24), C25(H25), C35(H35)
3.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C16(H16A,H16B), C34(H34A,H34B), C36(H36A,H36B)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2), C3(H3), C8(H8), C9(H9), C12(H12), C17(H17), C18(H18),
 C21(H21), C22(H22), C27(H27), C28(H28), C29(H29), C30(H30), C31(H31), C32(H32)
;
_shelx_res_checksum              98086
_shelx_hkl_checksum              37968
_olex2_submission_original_sample_id jb210814
_olex2_submission_special_instructions 'No special instructions were received'