Fluorinated Amine Stereotriads via Allene Amination
Liu, Lu; Gerstner, Nels C.; Oxtoby, Lucas J.; Guzei, Ilia A.; Schomaker, Jennifer M.; Organic Letters  (2017) –; doi:10.1021/acs.orglett.7b01342

data_1546196
_publ_section_title
;
 Fluorinated Amine Stereotriads via Allene Amination
;
_journal_name_full               'Organic Letters'
_journal_paper_doi               10.1021/acs.orglett.7b01342
_journal_year                    2017
_chemical_formula_moiety         '1(C16 H34 F N O4 S Si)'
_chemical_formula_sum            'C16 H34 F N O4 S Si'
_chemical_formula_weight         383.59
_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   mixed
_audit_creation_date             2015-10-05
_audit_creation_method
;
Olex2 1.2-dev
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                96.478(14)
_cell_angle_beta                 90.043(10)
_cell_angle_gamma                90.052(18)
_cell_formula_units_Z            8
_cell_length_a                   14.494(5)
_cell_length_b                   15.866(5)
_cell_length_c                   18.793(9)
_cell_measurement_reflns_used    9724
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.506
_cell_measurement_theta_min      2.182
_cell_volume                     4294(3)
_computing_cell_refinement       'SAINT+ Ver. 8.34A (Bruker-AXS, 2014)'
_computing_data_collection       'APEX2 Ver. 2014.11-0 (Bruker-AXS, 2014)'
_computing_data_reduction        'SAINT+ Ver. 8.34A (Bruker-AXS, 2014)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  'OLEX2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2015b)'
_computing_structure_solution    'XT (Sheldrick, 2015a)'
_diffrn_ambient_temperature      100.01
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '0.5\% \w and 0.5\% \f scans'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0584
_diffrn_reflns_av_unetI/netI     0.0680
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            60494
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         26.606
_diffrn_reflns_theta_min         1.090
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_exptl_absorpt_coefficient_mu    0.233
_exptl_absorpt_correction_T_max  0.8620
_exptl_absorpt_correction_T_min  0.6611
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Krause et al., 2015) was used for absorption correction.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.187
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1664
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.467
_refine_diff_density_min         -0.651
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1061
_refine_ls_number_reflns         17804
_refine_ls_number_restraints     278
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0690
_refine_ls_R_factor_gt           0.0498
_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^)+(0.0597P)^2^+0.8242P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1246
_refine_ls_wR_factor_ref         0.1337
_reflns_Friedel_coverage         0.000
_reflns_number_gt                13846
_reflns_number_total             17804
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b01342_si_002.cif
_cod_data_source_block           schomaker61
_cod_database_code               1546196
_shelx_estimated_absorpt_t_max   0.955
_shelx_estimated_absorpt_t_min   0.913
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.5832(9) 0.4168(9)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All N(H) groups
3. Restrained distances
 N1-H1 = N1A-H1AA = N1B-H1BA = N1C-H1C
 0.88 with sigma of 0.01
 C13C-C12C \\sim C13D-C12C
 with sigma of 0.02
 C14C-C13C \\sim C14D-C13D \\sim C15D-C14D \\sim C15C-C14C \\sim C16D-C15D
\\sim C16D-C15D
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uanis(Si1C) = Uanis(Si1D) = Uanis(Si1E)
Uanis(C2E) = Uanis(C5E)
5. Rigid body (RIGU) restrains
 C12C, C13C, C13D, C14C, C14D, C15C, C15D, C16C, C16D
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 Si1C, C1C, C2C, C3C, C4C, C5C, C6C
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 Si1D, C1D, C2D, C3D, C4D, C5D, C6D
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 Si1E, C1E, C2E, C3E, C4E, C5E, C6E
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
6. Same fragment restrains
{Si1C, O1C, C1C, C2C, C3C, C4C, C5C, C6C, C7C} sigma for 1-2: 0.01, 1-3: 0.02
{Si1D, O1C, C1D, C2D, C3D, C4D, C5D, C6D, C7C} sigma for 1-2: 0.01, 1-3: 0.02
{Si1E, O1C, C1E, C2E, C3E, C4E, C5E, C6E, C7C} sigma for 1-2: 0.005, 1-3: 0.01
as
{Si1, O1, C1, C2, C3, C4, C5, C6, C7}
7. Others
 1*[Sof(Si1C)+Sof(C1C)+Sof(H1CA)+Sof(H1CB)+Sof(H1CC)+Sof(C2C)+Sof(H2CA)+
 Sof(H2CB)+Sof(H2CC)+Sof(C3C)+Sof(H3CA)+Sof(H3CB)+Sof(H3CC)+Sof(C4C)+Sof(C5C)+
 Sof(H5CA)+Sof(H5CB)+Sof(H5CC)+Sof(C6C)+Sof(H6CA)+Sof(H6CB)+Sof(H6CC)]+1*
 [Sof(Si1D)+Sof(C1D)+Sof(H1DA)+Sof(H1DB)+Sof(H1DC)+Sof(C2D)+Sof(H2DA)+Sof(H2DB)+
 Sof(H2DC)+Sof(C3D)+Sof(H3DA)+Sof(H3DB)+Sof(H3DC)+Sof(C4D)+Sof(C5D)+Sof(H5DA)+
 Sof(H5DB)+Sof(H5DC)+Sof(C6D)+Sof(H6DA)+Sof(H6DB)+Sof(H6DC)]+1*[Sof(Si1E)+
 Sof(C1E)+Sof(H1EA)+Sof(H1EB)+Sof(H1EC)+Sof(C2E)+Sof(H2EA)+Sof(H2EB)+Sof(H2EC)+
 Sof(C3E)+Sof(H3EA)+Sof(H3EB)+Sof(H3EC)+Sof(C4E)+Sof(C5E)+Sof(H5EA)+Sof(H5EB)+
 Sof(H5EC)+Sof(C6E)+Sof(H6EA)+Sof(H6EB)+Sof(H6EC)]=1 with esd of 0
 Sof(Si1C)=Sof(C1C)=Sof(H1CA)=Sof(H1CB)=Sof(H1CC)=Sof(C2C)=Sof(H2CA)=Sof(H2CB)=
 Sof(H2CC)=Sof(C3C)=Sof(H3CA)=Sof(H3CB)=Sof(H3CC)=Sof(C4C)=Sof(C5C)=Sof(H5CA)=
 Sof(H5CB)=Sof(H5CC)=Sof(C6C)=Sof(H6CA)=Sof(H6CB)=Sof(H6CC)=FVAR(1)
 Sof(Si1D)=Sof(C1D)=Sof(H1DA)=Sof(H1DB)=Sof(H1DC)=Sof(C2D)=Sof(H2DA)=Sof(H2DB)=
 Sof(H2DC)=Sof(C3D)=Sof(H3DA)=Sof(H3DB)=Sof(H3DC)=Sof(C4D)=Sof(C5D)=Sof(H5DA)=
 Sof(H5DB)=Sof(H5DC)=Sof(C6D)=Sof(H6DA)=Sof(H6DB)=Sof(H6DC)=FVAR(2)
 Sof(Si1E)=Sof(C1E)=Sof(H1EA)=Sof(H1EB)=Sof(H1EC)=Sof(C2E)=Sof(H2EA)=Sof(H2EB)=
 Sof(H2EC)=Sof(C3E)=Sof(H3EA)=Sof(H3EB)=Sof(H3EC)=Sof(C4E)=Sof(C5E)=Sof(H5EA)=
 Sof(H5EB)=Sof(H5EC)=Sof(C6E)=Sof(H6EA)=Sof(H6EB)=Sof(H6EC)=FVAR(3)
 Sof(H12C)=Sof(H12D)=Sof(C13D)=Sof(H13C)=Sof(H13D)=Sof(C14D)=Sof(H14C)=
 Sof(H14D)=Sof(C15D)=Sof(H15C)=Sof(H15D)=Sof(C16D)=Sof(H16D)=Sof(H16E)=
 Sof(H16F)=1-FVAR(4)
 Sof(H12A)=Sof(H12B)=Sof(C13C)=Sof(H13A)=Sof(H13B)=Sof(C14C)=Sof(H14A)=
 Sof(H14B)=Sof(C15C)=Sof(H15A)=Sof(H15B)=Sof(C16C)=Sof(H16A)=Sof(H16B)=
 Sof(H16C)=FVAR(4)
8.a Ternary CH refined with riding coordinates:
 C7(H7), C10(H10), C11(H11), C7A(H7A), C10A(H10A), C11A(H11A), C7B(H7B),
 C10B(H10B), C11B(H11B), C7C(H7C), C10C(H10C), C11C(H11C)
8.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C12(H12E,H12F), C13(H13E,H13F), C14(H14E,H14F),
 C15(H15E,H15F), C8A(H8AA,H8AB), C9A(H9AA,H9AB), C12A(H12G,H12H), C13A(H13G,
 H13H), C14A(H14G,H14H), C15A(H15G,H15H), C8B(H8BA,H8BB), C9B(H9BA,H9BB),
 C12B(H12I,H12J), C13B(H13I,H13J), C14B(H14I,H14J), C15B(H15I,H15J), C8C(H8CA,
 H8CB), C9C(H9CA,H9CB), C12C(H12A,H12B), C12C(H12C,H12D), C13C(H13A,H13B),
 C14C(H14A,H14B), C15C(H15A,H15B), C13D(H13C,H13D), C14D(H14C,H14D), C15D(H15C,
 H15D)
8.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1D), C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C5(H5A,H5B,H5C), C6(H6A,
 H6B,H6C), C16(H16G,H16H,H16I), C1A(H1AB,H1AC,H1AD), C2A(H2AA,H2AB,H2AC),
 C3A(H3AA,H3AB,H3AC), C5A(H5AA,H5AB,H5AC), C6A(H6AA,H6AB,H6AC), C16A(H16J,H16K,
 H16L), C1B(H1BB,H1BC,H1BD), C2B(H2BA,H2BB,H2BC), C3B(H3BA,H3BB,H3BC), C5B(H5BA,
 H5BB,H5BC), C6B(H6BA,H6BB,H6BC), C16B(H16M,H16N,H16O), C1C(H1CA,H1CB,H1CC),
 C2C(H2CA,H2CB,H2CC), C3C(H3CA,H3CB,H3CC), C5C(H5CA,H5CB,H5CC), C6C(H6CA,H6CB,
 H6CC), C1E(H1EA,H1EB,H1EC), C2E(H2EA,H2EB,H2EC), C3E(H3EA,H3EB,H3EC), C5E(H5EA,
 H5EB,H5EC), C6E(H6EA,H6EB,H6EC), C1D(H1DA,H1DB,H1DC), C2D(H2DA,H2DB,H2DC),
 C3D(H3DA,H3DB,H3DC), C5D(H5DA,H5DB,H5DC), C6D(H6DA,H6DB,H6DC), C16C(H16A,H16B,
 H16C), C16D(H16D,H16E,H16F)
;
_shelx_res_checksum              39681
_shelx_hkl_checksum              36968
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'