Strain-Release Heteroatom Functionalization: Development, Scope, and Stereospecificity.
Lopchuk, Justin M.; Fjelbye, Kasper; Kawamata, Yu; Malins, Lara R.; Pan, Chung-Mao; Gianatassio, Ryan; Wang, Jie; Prieto, Liher; Bradow, James; Brandt, Thomas A.; Collins, Michael R.; Elleraas, Jeff; Ewanicki, Jason; Farrell, William; Fadeyi, Olugbeminiyi O.; Gallego, Gary M.; Mousseau, James J.; Oliver, Robert; Sach, Neal W.; Smith, Jason K.; Spangler, Jillian E.; Zhu, Huichin; Zhu, Jinjiang; Baran, Phil S.; Journal of the American Chemical Society 139 (2017) 3209–3226; doi:10.1021/jacs.6b13229

data_4125687
_publ_section_title
;
 Strain-Release Heteroatom Functionalization: Development, Scope, and
 Stereospecificity.
;
_journal_issue                   8
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3209
_journal_page_last               3226
_journal_paper_doi               10.1021/jacs.6b13229
_journal_volume                  139
_journal_year                    2017
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C22 H26 F2 N2 O2 S'
_chemical_formula_sum            'C22 H26 F2 N2 O2 S'
_chemical_formula_weight         420.53
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_primary     direct
_audit_creation_date             2016-07-15
_audit_creation_method
;
Olex2 1.2
(compiled Feb 16 2016 13:09:46 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.349(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5438(2)
_cell_length_b                   5.9781(1)
_cell_length_c                   35.8879(7)
_cell_measurement_reflns_used    9889
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      68.087
_cell_measurement_theta_min      3.695
_cell_volume                     2047.50(7)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2014.11-0 (Bruker, 2014)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.9295
_diffrn_measured_fraction_theta_max 0.9237
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker X8 APEX II'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            37183
_diffrn_reflns_theta_full        67.5000
_diffrn_reflns_theta_max         68.23
_diffrn_reflns_theta_min         2.46
_exptl_absorpt_coefficient_mu    1.742
_exptl_absorpt_correction_T_max  0.3200
_exptl_absorpt_correction_T_min  0.2232
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1025 before and 0.0549 after correction.
The Ratio of minimum to maximum transmission is 0.6975.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            Colorless
_exptl_crystal_colour_primary    Colorless
_exptl_crystal_density_diffrn    1.3641
_exptl_crystal_description       Needle
_exptl_crystal_F_000             892.1926
_exptl_crystal_size_max          0.261
_exptl_crystal_size_mid          0.149
_exptl_crystal_size_min          0.138
_refine_diff_density_max         0.2026
_refine_diff_density_min         -0.2726
_refine_diff_density_rms         0.0380
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.009(14)
_refine_ls_d_res_high            0.8301
_refine_ls_d_res_low             17.9436
_refine_ls_goodness_of_fit_ref   1.1535
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    88
_refine_ls_number_parameters     522
_refine_ls_number_reflns         6948
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.1535
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0335
_refine_ls_shift/su_max          0.0727
_refine_ls_shift/su_mean         0.0098
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0517P)^2^+0.4448P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0872
_refine_ls_wR_factor_ref         0.0973
_reflns_Friedel_coverage         0.884
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              6
_reflns_limit_k_min              -6
_reflns_limit_l_max              43
_reflns_limit_l_min              -42
_reflns_number_gt                6505
_reflns_number_total             6948
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            ja6b13229_si_015.cif
_cod_data_source_block           Baran594
_cod_original_sg_symbol_Hall     ' P 2yb'
_cod_database_code               4125687
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C4(H4), C1'(H1'), C4'(H4')
2.b Secondary CH2 refined with riding coordinates:
 C2(H2a,H2b), C3(H3a,H3b), C5(H5a,H5b), C6(H6a,H6b), C7(H7a,H7b), C8(H8a,H8b),
 C9(H9a,H9b), C10(H10a,H10b), C2'(H2'a,H2'b), C3'(H3'a,H3'b), C5'(H5'a,H5'b),
 C6'(H6'a,H6'b), C7'(H7'a,H7'b), C8'(H8'a,H8'b), C9'(H9'a,H9'b), C10'(H10c,H10d)
2.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C18(H18), C20(H20),
 C22(H22), C12'(H12'), C13'(H13'), C14'(H14'), C15'(H15'), C16'(H16'),
 C18'(H18'), C20'(H20'), C22'(H22')
;
_olex2_submission_special_instructions 'No special instructions were received'