Stereoselective construction of sterically hindered oxaspirocycles <i>via</i> chiral bidentate directing group-mediated C(sp<sup>3</sup>)-O bond formation.
Kim, Yechan; Kim, Seoung-Tae; Kang, Dahye; Sohn, Te-Ik; Jang, Eunyoung; Baik, Mu-Hyun; Hong, Sungwoo; Chemical science 9 (2018) 1473–1480; doi:10.1039/c7sc04691j

data_1548241
_publ_section_title
;
 Stereoselective construction of sterically hindered oxaspirocycles
 <i>via</i> chiral bidentate directing group-mediated C(sp<sup>3</sup>)-O
 bond formation.
;
_journal_issue                   6
_journal_name_full               'Chemical science'
_journal_page_first              1473
_journal_page_last               1480
_journal_paper_doi               10.1039/c7sc04691j
_journal_volume                  9
_journal_year                    2018
_chemical_formula_sum            'C16 H23 N2 O2'
_chemical_formula_weight         275.36
_chemical_name_systematic
N-((S)-2,2-dimethyl-1-(pyridin-2-yl)propyl)-2-((S)-tetrahydrofuran-2-yl)acetamide
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-10-25 deposited with the CCDC.
2017-11-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.8237(4)
_cell_length_b                   9.6779(6)
_cell_length_c                   23.2090(13)
_cell_measurement_reflns_used    9325
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      33.139
_cell_measurement_theta_min      3.372
_cell_volume                     1532.70(16)
_computing_cell_refinement       'Bruker SMART APEXll'
_computing_data_collection       'Bruker SMART APEXll'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    SHELXTL
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega phi scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_unetI/netI     0.0098
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            90932
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.198
_diffrn_reflns_theta_min         3.371
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6249
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_description       block
_exptl_crystal_F_000             596
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.240
_refine_diff_density_max         0.607
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 2400 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.09(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         5861
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0338
_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^)+(0.0609P)^2^+0.2023P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0981
_refine_ls_wR_factor_ref         0.0995
_reflns_Friedel_coverage         0.758
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                5677
_reflns_number_total             5861
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7sc04691j2.cif
_cod_data_source_block           p212121_a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'MULTI-SCAN' changed to
'multi-scan' according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 1548241.cif.
;
_cod_database_code               1548241
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.971
_shelx_estimated_absorpt_t_max   0.981
_shelx_res_checksum              92914