Synthesis of Highly Functionalized Decalins via Metallacycle-Mediated Cross-Coupling.
Mizoguchi, Haruki; Micalizio, Glenn C.; Journal of the American Chemical Society 137 (2015) 6624–6628; doi:10.1021/jacs.5b02107

data_4123592
_publ_section_title
;
 Synthesis of Highly Functionalized Decalins via Metallacycle-Mediated
 Cross-Coupling.
;
_journal_issue                   20
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6624
_journal_page_last               6628
_journal_paper_doi               10.1021/jacs.5b02107
_journal_volume                  137
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C27 H39 N O4 Si'
_chemical_formula_sum            'C27 H39 N O4 Si'
_chemical_formula_weight         469.68
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2015-01-16
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2015.01.16 svn.r3137 for OlexSys, GUI svn.r4992)
;
_cell_angle_alpha                90
_cell_angle_beta                 105.3750(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.4286(9)
_cell_length_b                   9.6835(6)
_cell_length_c                   21.6664(14)
_cell_measurement_reflns_used    9735
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.337
_cell_measurement_theta_min      2.318
_cell_volume                     2716.6(3)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'COSMO (BRUKER, V1.61, 2009)'
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 836.6
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            45415
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.375
_diffrn_reflns_theta_min         1.573
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0753 before and 0.0498 after correction. The Ratio of minimum to maximum transmission is 0.9341. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.148
_exptl_crystal_description       chunk
_exptl_crystal_F_000             1016
_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.307
_exptl_crystal_size_mid          0.218
_exptl_crystal_size_min          0.142
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
 Flack x determined using 3556 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     607
_refine_ls_number_reflns         9961
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0393
_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^)+(0.0498P)^2^+0.3639P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0910
_refine_ls_wR_factor_ref         0.0979
_reflns_Friedel_coverage         0.879
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                8457
_reflns_number_total             9961
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b02107_si_001.cif
_cod_data_source_block           gcm115a
_cod_depositor_comments          'Adding full bibliography for 4123592.cif.'
_cod_database_code               4123592
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.965
_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.a Ternary CH refined with riding coordinates:
 C12(H12), C21(H21), C26(H26), C27(H27), C28(H28), C29(H29), C32(H32),
 C37(H37), C38(H38), C51(H51), C55(H55), C56(H56)
2.b Secondary CH2 refined with riding coordinates:
 C34(H34A,H34B), C35(H35A,H35B), C40(H40A,H40B), C43(H43A,H43B), C44(H44A,
 H44B), C45(H45A,H45B), C46(H46A,H46B), C48(H48A,H48B), C54(H54A,H54B),
 C57(H57A,H57B)
2.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C16(H16), C18(H18), C20(H20), C30(H30), C31(H31), C33(H33),
 C39(H39), C42(H42), C53(H53)
2.d Idealised Me refined as rotating group:
 C49(H49A,H49B,H49C), C50(H50A,H50B,H50C), C52(H52A,H52B,H52C), C58(H58A,H58B,
 H58C), C59(H59A,H59B,H59C), C61(H61A,H61B,H61C), C62(H62A,H62B,H62C), C63(H63A,
 H63B,H63C), C64(H64A,H64B,H64C), C65(H65A,H65B,H65C), C70(H70A,H70B,H70C),
 C71(H71A,H71B,H71C)
;
_contact_crystallographer_email  staples@chemistry.msu.com
_contact_crystallographer_name   'Richard Staples'
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_special_instructions 'No special instructions were received'