Reductive Elimination at Carbon under Steric Control.
Tolentino, Daniel R.; Neale, Samuel E.; Isaac, Connie J.; Macgregor, Stuart A.; Whittlesey, Michael K.; Jazzar, Rodolphe; Bertrand, Guy; Journal of the American Chemical Society 141 (2019) 9823–9826; doi:10.1021/jacs.9b04957

data_4128284
_publ_section_title
;
 Reductive Elimination at Carbon under Steric Control.
;
_journal_issue                   25
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9823
_journal_page_last               9826
_journal_paper_doi               10.1021/jacs.9b04957
_journal_volume                  141
_journal_year                    2019
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C27 H43 N S'
_chemical_formula_sum            'C27 H43 N S'
_chemical_formula_weight         413.68
_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_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-05-07
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 102.399(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.6679(4)
_cell_length_b                   18.7513(7)
_cell_length_c                   13.8244(5)
_cell_measurement_reflns_used    4778
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      68.73
_cell_measurement_theta_min      4.68
_cell_volume                     2447.71(16)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.15
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            36974
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.614
_diffrn_reflns_theta_min         3.273
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.242
_exptl_absorpt_correction_T_max  0.7491
_exptl_absorpt_correction_T_min  0.6714
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0751 before and 0.0684 after correction. The Ratio of minimum to maximum transmission is 0.8963. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.123
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 4134 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.076(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     623
_refine_ls_number_reflns         9584
_refine_ls_number_restraints     105
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0350
_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^)+(0.0392P)^2^+0.5990P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0859
_refine_ls_wR_factor_ref         0.0871
_reflns_Friedel_coverage         0.923
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.979
_reflns_number_gt                9164
_reflns_number_total             9584
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            4_MenthCAACS.cif
_cod_data_source_block           4_menthcaacs
_cod_database_code               4128284
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.941
_shelx_estimated_absorpt_t_min   0.941
_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
 C2-C11A = C7A-C2
 1.55 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C7A) = Uanis(C13)
Uanis(C3A) = Uanis(C3)
4. Rigid body (RIGU) restrains
 C7, C8, C9, C10, C11, C12, C13, C14, C15
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C7A, C8A, C9A, C10A, C11A, C12A, C13A, C14A, C15A
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
5. Others
 Sof(C3)=Sof(H3A)=Sof(H3B)=Sof(C7)=Sof(H7A)=Sof(H7B)=Sof(C8)=Sof(H8)=Sof(C9)=
 Sof(H9A)=Sof(H9B)=Sof(C10)=Sof(H10A)=Sof(H10B)=Sof(C11)=Sof(H11)=Sof(C12)=
 Sof(H12A)=Sof(H12B)=Sof(H12C)=Sof(C13)=Sof(H13)=Sof(C14)=Sof(H14A)=Sof(H14B)=
 Sof(H14C)=Sof(C15)=Sof(H15A)=Sof(H15B)=Sof(H15C)=1-FVAR(1)
 Sof(C3A)=Sof(H3AA)=Sof(H3AB)=Sof(C7A)=Sof(H7AA)=Sof(H7AB)=Sof(C8A)=Sof(H8A)=
 Sof(C9A)=Sof(H9AA)=Sof(H9AB)=Sof(C10A)=Sof(H10C)=Sof(H10D)=Sof(C11A)=Sof(H11A)=
 Sof(C12A)=Sof(H12D)=Sof(H12E)=Sof(H12F)=Sof(C13A)=Sof(H13A)=Sof(C14A)=
 Sof(H14D)=Sof(H14E)=Sof(H14F)=Sof(C15A)=Sof(H15D)=Sof(H15E)=Sof(H15F)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C8(H8), C8A(H8A), C11(H11), C11A(H11A), C13(H13), C13A(H13A), C22(H22),
 C25(H25), C35(H35), C38(H38), C40(H40), C49(H49), C52(H52)
6.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C3A(H3AA,H3AB), C7(H7A,H7B), C7A(H7AA,H7AB), C9(H9A,H9B),
 C9A(H9AA,H9AB), C10(H10A,H10B), C10A(H10C,H10D), C30(H30A,H30B), C34(H34A,
 H34B), C36(H36A,H36B), C37(H37A,H37B)
6.c Aromatic/amide H refined with riding coordinates:
 C18(H18), C19(H19), C20(H20), C45(H45), C46(H46), C47(H47)
6.d Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C12(H12A,H12B,H12C), C12A(H12D,H12E,H12F),
 C14(H14A,H14B,H14C), C14A(H14D,H14E,H14F), C15(H15A,H15B,H15C), C15A(H15D,H15E,
 H15F), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C26(H26A,H26B,H26C), C27(H27A,
 H27B,H27C), C32(H32A,H32B,H32C), C33(H33A,H33B,H33C), C39(H39A,H39B,H39C),
 C41(H41A,H41B,H41C), C42(H42A,H42B,H42C), C50(H50A,H50B,H50C), C51(H51A,H51B,
 H51C), C53(H53A,H53B,H53C), C54(H54A,H54B,H54C)
;
_shelx_res_checksum              80631
_shelx_hkl_checksum              67300
_olex2_submission_special_instructions 'No special instructions were received'