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_1520614
_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         'C25 H23 N O3'
_chemical_formula_sum            'C25 H23 N O3'
_chemical_formula_weight         385.44
_chemical_name_systematic
2-(benzyl(3-((4-methoxyphenyl)ethynyl)oxetan-3-yl)amino)phenol
_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     iterative
_audit_creation_date             2015-03-17
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 92.942(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4141(7)
_cell_length_b                   23.2930(14)
_cell_length_c                   9.0609(6)
_cell_measurement_reflns_used    9728
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      27.52
_cell_measurement_theta_min      2.41
_cell_volume                     1984.3(2)
_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    'olex2.solve (Bourhis et al., 2015)'
_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/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  0.0348
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            33820
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.534
_diffrn_reflns_theta_min         2.166
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7207
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0578 before and 0.0479 after correction.
The Ratio of minimum to maximum transmission is 0.9666.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         4567
_refine_ls_number_restraints     326
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0388
_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^)+(0.0465P)^2^+0.7647P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0926
_refine_ls_wR_factor_ref         0.0987
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3865
_reflns_number_total             4567
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b01607_si_002.cif
_cod_data_source_block           ca110315_1_1_0ma
_cod_depositor_comments
'Adding full bibliography for 1520614--1520615.cif.'
_cod_database_code               1520614
_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 C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O1-C2 \\sim O1A-C2 \\sim O1-C3 \\sim O1A-C3
 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(O1) \\sim Ueq, Uanis(O1A) \\sim Ueq: with sigma of 0.001 and sigma for
terminal atoms of 0.001
Uanis(O1) = Uanis(O1A)
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(H2BC)=Sof(H2BD)=Sof(H3BC)=Sof(H3BD)=Sof(O1A)=1-FVAR(1)
 Sof(H2AA)=Sof(H2AB)=Sof(H3AA)=Sof(H3AB)=Sof(O1)=FVAR(1)
7.a Secondary CH2 refined with riding coordinates:
 C2(H2AA,H2AB), C2(H2BC,H2BD), C13(H13A,H13B), C3(H3AA,H3AB), C3(H3BC,H3BD)
7.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C24(H24), C10(H10), C23(H23), C15(H15), C25(H25), C8(H8), C7(H7),
 C19(H19), C20(H20), C16(H16), C18(H18), C17(H17)
7.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
7.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_shelx_res_checksum              43386
_shelx_hkl_checksum              71371
_olex2_date_sample_data_collection 2015-03-11
_olex2_date_sample_submission    2015-03-11
_olex2_submission_original_sample_id ca110315_1_1
_olex2_submission_special_instructions 'No special instructions were received'