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_4128286
_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         '2(C34 H54 N2), C5 H12'
_chemical_formula_sum            'C73 H120 N4'
_chemical_formula_weight         1053.72
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 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                79.515(5)
_cell_angle_beta                 87.442(5)
_cell_angle_gamma                85.632(5)
_cell_formula_units_Z            1
_cell_length_a                   9.4457(8)
_cell_length_b                   9.7034(10)
_cell_length_c                   18.412(2)
_cell_measurement_reflns_used    9988
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      25.41
_cell_measurement_theta_min      2.25
_cell_volume                     1653.7(3)
_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)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.0
_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 0.996
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_av_unetI/netI     0.0548
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            31865
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.418
_diffrn_reflns_theta_min         2.140
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.060
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1046 before and 0.0532 after correction. The Ratio of minimum to maximum transmission is 0.9389. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.058
_exptl_crystal_description       block
_exptl_crystal_F_000             586
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.023
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 3847 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.4(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     797
_refine_ls_number_reflns         12106
_refine_ls_number_restraints     48
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0461
_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^)+(0.0459P)^2^+0.3491P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1038
_refine_ls_wR_factor_ref         0.1140
_reflns_Friedel_coverage         0.990
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                9686
_reflns_number_total             12106
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            7_MenthCAACCNCy.cif
_cod_data_source_block           7_menthcaaccncy
_cod_original_cell_volume        1653.8(3)
_cod_database_code               4128286
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.999
_shelx_estimated_absorpt_t_min   0.986
_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, All C(H,H,H,H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C71A) = Uanis(C71B)
Uanis(C72B) = Uanis(C72A)
Uanis(C73A) = Uanis(C73B)
Uanis(C34A) = Uanis(C1D)
Uanis(C31A) = Uanis(C1I)
3. Rigid body (RIGU) restrains
 C70B, C71B, C72B, C73B, C74B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C71A, C72A, C73A, C70B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C1B, C1C, C1D
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(C71A)=Sof(H71A)=Sof(H71B)=Sof(C72A)=Sof(H72A)=Sof(H72B)=Sof(C73A)=
 Sof(H73A)=Sof(H73B)=Sof(H70D)=Sof(H70E)=Sof(H70F)=Sof(H74D)=Sof(H74E)=
 Sof(H74F)=1-FVAR(1)
 Sof(H70A)=Sof(H70B)=Sof(H70C)=Sof(C71B)=Sof(H71C)=Sof(H71D)=Sof(C72B)=
 Sof(H72C)=Sof(H72D)=Sof(C73B)=Sof(H73C)=Sof(H73D)=Sof(H74A)=Sof(H74B)=
 Sof(H74C)=FVAR(1)
 Sof(C1B)=Sof(H1BA)=Sof(H1BB)=Sof(H1BC)=Sof(C1C)=Sof(H1C)=Sof(C1D)=Sof(H1DA)=
 Sof(H1DB)=Sof(H1DC)=Sof(C1E)=Sof(H1E)=Sof(C1F)=Sof(H1FA)=Sof(H1FB)=Sof(C1G)=
 Sof(H1GA)=Sof(H1GB)=Sof(C1H)=Sof(H1H)=Sof(C1I)=Sof(H1IA)=Sof(H1IB)=Sof(C1J)=
 Sof(H1JA)=Sof(H1JB)=Sof(H1JC)=1-FVAR(2)
 Sof(C26A)=Sof(H26A)=Sof(H26B)=Sof(C27A)=Sof(H27A)=Sof(C28A)=Sof(H28A)=
 Sof(H28B)=Sof(C29A)=Sof(H29A)=Sof(H29B)=Sof(C30A)=Sof(H30A)=Sof(C31A)=
 Sof(H31A)=Sof(C32A)=Sof(H32A)=Sof(H32B)=Sof(H32C)=Sof(C33A)=Sof(H33A)=
 Sof(H33B)=Sof(H33C)=Sof(C34A)=Sof(H34A)=Sof(H34B)=Sof(H34C)=FVAR(2)
5.a Ternary CH refined with riding coordinates:
 C3(H3), C20(H20), C23(H23), C27(H27), C30(H30), C31(H31), C3A(H3A),
 C20A(H20A), C23A(H23A), C27A(H27A), C30A(H30A), C31A(H31A), C1C(H1C), C1E(H1E),
  C1H(H1H)
5.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C10(H10C,
 H10D), C26(H26C,H26D), C28(H28C,H28D), C29(H29C,H29D), C4A(H4AA,H4AB),
 C5A(H5AA,H5AB), C6A(H6AA,H6AB), C7A(H7AA,H7AB), C8A(H8AA,H8AB), C10A(H10A,
 H10B), C26A(H26A,H26B), C28A(H28A,H28B), C29A(H29A,H29B), C71A(H71A,H71B),
 C72A(H72A,H72B), C73A(H73A,H73B), C71B(H71C,H71D), C72B(H72C,H72D), C73B(H73C,
 H73D), C1F(H1FA,H1FB), C1G(H1GA,H1GB), C1I(H1IA,H1IB)
5.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C17(H17), C18(H18), C16A(H16A), C17A(H17A), C18A(H18A)
5.d Idealised Me refined as rotating group:
 C12(H12D,H12E,H12F), C13(H13D,H13E,H13F), C21(H21D,H21E,H21F), C22(H22D,H22E,
 H22F), C24(H24D,H24E,H24F), C25(H25D,H25E,H25F), C32(H32D,H32E,H32F), C33(H33D,
 H33E,H33F), C34(H34D,H34E,H34F), C12A(H12A,H12B,H12C), C13A(H13A,H13B,H13C),
 C21A(H21A,H21B,H21C), C22A(H22A,H22B,H22C), C24A(H24A,H24B,H24C), C25A(H25A,
 H25B,H25C), C32A(H32A,H32B,H32C), C33A(H33A,H33B,H33C), C34A(H34A,H34B,H34C),
 C1B(H1BA,H1BB,H1BC), C70B(H70A,H70B,H70C), C70B(H70D,H70E,H70F), C74B(H74A,
 H74B,H74C), C74B(H74D,H74E,H74F), C1D(H1DA,H1DB,H1DC), C1J(H1JA,H1JB,H1JC)
;
_shelx_res_checksum              26107
_shelx_hkl_checksum              46775
_olex2_submission_special_instructions 'No special instructions were received'