Addition of Trifluoroborates to Oxetanyl N,O-Acetals: Entry into Spiro and Fused Saturated Heterocycles.
Brady, Patrick B.; Carreira, Erick M.; Organic letters 17 (2015) 3350–3353; doi:10.1021/acs.orglett.5b01607

data_1520615
_publ_section_title
;
 Addition of Trifluoroborates to Oxetanyl N,O-Acetals: Entry into Spiro
 and Fused Saturated Heterocycles.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3350
_journal_page_last               3353
_journal_paper_doi               10.1021/acs.orglett.5b01607
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C18 H17 N O2'
_chemical_formula_sum            'C18 H17 N O2'
_chemical_formula_weight         279.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2015-03-27
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 98.788(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.0166(6)
_cell_length_b                   15.8594(12)
_cell_length_c                   11.2674(9)
_cell_measurement_reflns_used    8069
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      2.57
_cell_volume                     1415.70(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      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 1.000
_diffrn_measured_fraction_theta_max 0.999
_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  0.0373
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            29014
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.544
_diffrn_reflns_theta_min         2.235
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0494 before and 0.0450 after correction. The Ratio of minimum to maximum transmission is 0.9378. The \l/2 correction factor is 0.00150.'
_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    1.311
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.464
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3281
_refine_ls_number_restraints     300
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0434
_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^)+(0.0438P)^2^+0.7346P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1039
_refine_ls_wR_factor_ref         0.1090
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2763
_reflns_number_total             3281
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b01607_si_003.cif
_cod_data_source_block           mo_ca270315_1_1_0m
_cod_depositor_comments
'Adding full bibliography for 1520614--1520615.cif.'
_cod_database_code               1520615
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.982
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C18-C15 = C18A-C15
 1.585 with sigma of 0.002
 C16A-C15 \\sim C16-C15
 with sigma of 0.02
 C17-C16 \\sim C16A-C17A
 with sigma of 0.02
 O2-C17 \\sim O2A-C17A
 with sigma of 0.02
 O2-C18 \\sim O2A-C18A
 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. Uiso/Uaniso restraints and constraints
Uanis(C18A) \\sim Ueq: with sigma of 0.003 and sigma for terminal atoms of 0.006
5. 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
6. Others
 Sof(C18A)=Sof(H18C)=Sof(H18D)=Sof(C16A)=Sof(H16A)=Sof(C17A)=Sof(H17A)=
 Sof(O2A)=1-FVAR(1)
 Sof(O2)=Sof(C18)=Sof(H18A)=Sof(H18B)=Sof(C16)=Sof(H16)=Sof(C17)=Sof(H17)=
 FVAR(1)
7.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C14(H14A,H14B), C18(H18A,H18B), C18A(H18C,H18D)
7.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12), C3(H3), C7(H7), C5(H5), C6(H6), C4(H4),
 C16(H16), C17(H17), C16A(H16A), C17A(H17A)
;
_shelx_res_checksum              53883
_shelx_hkl_checksum              97372
_olex2_date_sample_data_collection 2015-03-26
_olex2_date_sample_submission    2015-03-26
_olex2_submission_original_sample_id ca270315_1_1
_olex2_submission_special_instructions 'No special instructions were received'