Co(III)-Catalyzed Z-Selective Oxidative C–H/C–H Cross-Coupling of Alkenes with Triisopropylsilylacetylene
Zhao, Tingxing; Qin, Dekun; Han, Weiguo; Yang, Shiping; Feng, Boya; Gao, Ge; You, Jingsong; Chemical Communications  (2019) –; doi:10.1039/C9CC02347J

data_7123382
_publ_section_title
;
 Co(III)-Catalyzed Z-Selective Oxidative C--H/C--H Cross-Coupling of
 Alkenes with Triisopropylsilylacetylene
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC02347J
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C41 H53 N3 O Si'
_chemical_formula_sum            'C41 H53 N3 O Si'
_chemical_formula_weight         631.95
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2018-12-03
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-01-04 deposited with the CCDC.    2019-05-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.7365(17)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.7444(2)
_cell_length_b                   12.6901(2)
_cell_length_c                   24.3021(5)
_cell_measurement_reflns_used    9198
_cell_measurement_temperature    150
_cell_measurement_theta_max      72.5480
_cell_measurement_theta_min      5.1420
_cell_volume                     3621.63(11)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details
;
  1 omega  -31.00   53.00   1.0000    1.6100
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -57.0000  -30.0000 84

  2 omega    1.00   27.00   1.0000    1.6100
omega____ theta____ kappa____ phi______ frames
    -       36.2921   93.0000  -17.9619 26

  3 omega    1.00   75.00   1.0000    1.6100
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -99.0000  -90.0000 74

  4 omega   10.00  104.00   1.0000    1.6100
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000  -60.0000 94

  5 omega   10.00  104.00   1.0000    1.6100
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000  -90.0000 94

  6 omega   17.00  105.00   1.0000    1.6100
omega____ theta____ kappa____ phi______ frames
    -       36.2921   38.0000   90.0000 88

  7 omega   90.00  175.00   1.0000    6.4300
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  120.0000 85

  8 omega   91.00  176.00   1.0000    6.4300
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -120.0000 85

  9 omega   39.00  109.00   1.0000    6.4300
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -150.0000 70

 10 omega   40.00   98.00   1.0000    6.4300
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -120.0000 58

 11 omega   40.00   98.00   1.0000    6.4300
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 58

 12 omega   38.00   91.00   1.0000    6.4300
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 53

 13 omega   38.00   91.00   1.0000    6.4300
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 53

 14 omega   38.00   91.00   1.0000    6.4300
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -60.0000 53

 15 omega   39.00  109.00   1.0000    6.4300
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -90.0000 70

 16 omega   37.00  146.00   1.0000    6.4300
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000  120.0000 109

 17 omega   20.00  104.00   1.0000    1.6100
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000 -180.0000 84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1282673000
_diffrn_orient_matrix_UB_12      0.0246959000
_diffrn_orient_matrix_UB_13      0.0026426000
_diffrn_orient_matrix_UB_21      -0.0025082000
_diffrn_orient_matrix_UB_22      0.0205665000
_diffrn_orient_matrix_UB_23      -0.0624447000
_diffrn_orient_matrix_UB_31      -0.0277433000
_diffrn_orient_matrix_UB_32      -0.1170358000
_diffrn_orient_matrix_UB_33      -0.0105495000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            21329
_diffrn_reflns_point_group_measured_fraction_full 0.789
_diffrn_reflns_point_group_measured_fraction_max 0.764
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.883
_diffrn_reflns_theta_min         5.132
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.830
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61390
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.159
_exptl_crystal_description       plate
_exptl_crystal_F_000             1368
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.877
_refine_diff_density_min         -0.653
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details
;
 Flack x determined using 3098 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.000(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     845
_refine_ls_number_reflns         11042
_refine_ls_number_restraints     40
_refine_ls_restrained_S_all      1.117
_refine_ls_R_factor_all          0.0779
_refine_ls_R_factor_gt           0.0742
_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^)+(0.1361P)^2^+1.7440P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2000
_refine_ls_wR_factor_ref         0.2066
_reflns_Friedel_coverage         0.482
_reflns_Friedel_fraction_full    0.557
_reflns_Friedel_fraction_max     0.522
_reflns_number_gt                10324
_reflns_number_total             11042
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc02347j2.cif
_cod_data_source_block           zyx-150k
_cod_original_cell_volume        3621.63(12)
_cod_database_code               7123382
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C2-C1
 1.52 with sigma of 0.01
3. Rigid bond restraints
 C2, C4
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C1, C02B
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C2, C02C
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C02C, C4
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C1, C2
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C023, C026
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C1, C4
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 Si01, C1
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Uiso/Uaniso restraints and constraints
C023 \\sim C026: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02
Uanis(C1) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(Si01)
\\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
5.a Ternary CH refined with riding coordinates:
 C00G(H00G), C00H(H00H), C00I(H00I), C00M(H00M), C00V(H00V), C011(H011),
 C017(H017), C01J(H2AA), C01O(H01O), C01P(H01P), C023(H023), C02B(H02C),
 C02D(H02P), C1(H1)
5.b Secondary CH2 refined with riding coordinates:
 C00J(H00J,H00K), C00N(H00L,H00N), C00P(H00O,H00P), C00X(H00D,H00E), C010(H01A,
 H01B), C013(H01X,H01Y), C014(H01Z,H), C01B(H01C,H01D), C01I(H1AA,HC),
 C01K(H3AA,HD), C01N(H01K,H01L), C01U(H01R,H01U), C01X(H01V,H01W), C02A(H02A,
 H02B)
5.c Aromatic/amide H refined with riding coordinates:
 N006(H006), N007(H007), C00B(H00F), C018(H018), C01E(H0AA), C01S(H01S),
 C01T(H01T), C01W(H5AA), C01Z(H6AA), C021(H021), C022(H022), C024(H024),
 C025(H025), C027(H027), C028(H028), C029(H029)
5.d Idealised Me refined as rotating group:
 C00S(H00A,H00B,H00C), C00Y(H00Q,H00R,H00S), C015(H01,HA,HB), C01D(H01E,H01F,
 H01G), C01H(H01H,H01I,H01J), C01Q(H01M,H01N,H01Q), C01R(H4AA,HE,HF), C020(H02J,
 H02K,H02L), C026(H02M,H02N,H02O), C02C(H02D,H02E,H02F), C02F(H02Q,H02R,H02S),
 C02G(H02T,H02U,H02V), C02H(H02W,H02X,H02Y), C02I(H02G,H02H,H02I), C2(H2A,H2B,
 H2C), C4(H4A,H4B,H4C)
;
_shelx_res_checksum              87197
_olex2_submission_special_instructions 'No special instructions were received'