Enantioselective Intermolecular C-H Functionalization of Allylic and Benzylic sp(3) C-H Bonds Using N-Sulfonyl-1,2,3-triazoles.
Kubiak, 2nd, Robert W; Mighion, Jeffrey D.; Wilkerson-Hill, Sidney M; Alford, Joshua S.; Yoshidomi, Tetsushi; Davies, Huw M. L.; Organic letters 18 (2016) 3118–3121; doi:10.1021/acs.orglett.6b01298

data_1555585
_publ_section_title
;
 Enantioselective Intermolecular C-H Functionalization of Allylic and
 Benzylic sp(3) C-H Bonds Using N-Sulfonyl-1,2,3-triazoles.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3118
_journal_page_last               3121
_journal_paper_doi               10.1021/acs.orglett.6b01298
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H23 N O2 S'
_chemical_formula_sum            'C15 H23 N O2 S'
_chemical_formula_weight         281.40
_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'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2016-01-14
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2015.11.10 svn.r3248 for OlexSys, GUI svn.r5133)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.5067(4)
_cell_length_b                   10.2546(7)
_cell_length_c                   22.3875(14)
_cell_measurement_reflns_used    8512
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      30.907
_cell_measurement_theta_min      2.18
_cell_volume                     1493.77(17)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2014.1-1 (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  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      110(2)
_diffrn_detector_area_resol_mean 512
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_av_unetI/netI     0.0519
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            13470
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         31.058
_diffrn_reflns_theta_min         2.694
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.215
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.5490
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1779 before and 0.0715 after correction.
The Ratio of minimum to maximum transmission is 0.7357.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_description       needle
_exptl_crystal_F_000             608
_exptl_crystal_recrystallization_method 'Slow evaporation from hexanes'
_exptl_crystal_size_max          1.251
_exptl_crystal_size_mid          0.134
_exptl_crystal_size_min          0.102
_refine_diff_density_max         0.686
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.076
_refine_ls_abs_structure_details
;
 Flack x determined using 1617 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         4751
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0469
_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^)+(0.0681P)^2^+0.3052P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1122
_refine_ls_wR_factor_ref         0.1193
_reflns_Friedel_coverage         0.737
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                4250
_reflns_number_total             4751
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b01298_si_002.cif
_cod_data_source_block           a415
_cod_database_code               1555585
_shelx_estimated_absorpt_t_max   0.978
_shelx_estimated_absorpt_t_min   0.775
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N1-H1
 0.955 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C1(H009)
3.b Secondary CH2 refined with riding coordinates:
 C2(H00C,H00D)
3.c Aromatic/amide H refined with riding coordinates:
 C7(H006), C12(H007), C8(H00E), C13(H00F), C11(H00G), C15(H00H), C14(H00L)
3.d Idealised Me refined as rotating group:
 C6(H00I,H00J,H00K), C9(H00M,H00N,H00O), C3(H00P,H00Q,H00R), C5(H00S,H00T,H00U)
;
_shelx_res_checksum              35089
_shelx_hkl_checksum              14102
_shelx_shelxl_version_number     2014/7
_olex2_exptl_crystal_mounting_method 'Mounted on a loop with paratone oil'
_olex2_submission_original_sample_id rwk2-02-10
_olex2_submission_special_instructions 'No special instructions were received'