SmCp<sup>R</sup><sub>2</sub>-mediated cross-coupling of allyl and propargyl ethers with ketoesters and a telescoped approach to complex cycloheptanols.
Plesniak, Mateusz P.; Just-Baringo, Xavier; Ortu, Fabrizio; Mills, David P.; Procter, David J.; Chemical communications (Cambridge, England) 52 (2016) 13503–13506; doi:10.1039/c6cc07318b

data_7125178
_publ_section_title
;
 SmCp<sup>R</sup><sub>2</sub>-mediated cross-coupling of allyl and
 propargyl ethers with ketoesters and a telescoped approach to complex
 cycloheptanols.
;
_journal_issue                   92
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              13503
_journal_page_last               13506
_journal_paper_doi               10.1039/c6cc07318b
_journal_volume                  52
_journal_year                    2016
_chemical_formula_moiety         'C32 H66 O Si6 Sm'
_chemical_formula_sum            'C32 H66 O Si6 Sm'
_chemical_formula_weight         785.73
_chemical_properties_physical    ', Air-sensitive,Moisture-sensitive'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-07-09
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2016-08-29 deposited with the CCDC.
2016-10-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.974(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.2870(3)
_cell_length_b                   22.3415(7)
_cell_length_c                   16.9210(5)
_cell_measurement_reflns_used    6323
_cell_measurement_temperature    150.01(13)
_cell_measurement_theta_max      27.8930
_cell_measurement_theta_min      3.6510
_cell_volume                     4225.7(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      150.01(13)
_diffrn_detector_area_resol_mean 8.0714
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -16.00   88.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -       19.4509    0.0000  120.0000 104

  2 omega   63.00   96.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -       19.4509 -178.0000    0.0000 33

  3 omega  -90.00  -39.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.3571 -178.0000 -150.0000 51

  4 omega   39.00   89.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -       19.4509  178.0000 -180.0000 50
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0616355000
_diffrn_orient_matrix_UB_12      0.0044240000
_diffrn_orient_matrix_UB_13      0.0023498000
_diffrn_orient_matrix_UB_21      -0.0129250000
_diffrn_orient_matrix_UB_22      -0.0287082000
_diffrn_orient_matrix_UB_23      -0.0170093000
_diffrn_orient_matrix_UB_31      0.0076754000
_diffrn_orient_matrix_UB_32      -0.0128605000
_diffrn_orient_matrix_UB_33      0.0386696000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_unetI/netI     0.0649
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17017
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_min         3.361
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.581
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.833
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_description       block
_exptl_crystal_F_000             1648
_exptl_crystal_size_max          0.2346
_exptl_crystal_size_mid          0.1304
_exptl_crystal_size_min          0.0846
_refine_diff_density_max         1.196
_refine_diff_density_min         -0.509
_refine_diff_density_rms         0.102
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         7723
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0438
_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^)+(0.0284P)^2^+5.0623P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0846
_refine_ls_wR_factor_ref         0.0918
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6037
_reflns_number_total             7723
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc07318b2.cif
_cod_data_source_block           5c
_cod_database_code               7125178
_manchester_internal_coll_name   adpm109
_manchester_internal_coll_client MP/DP/DPM
_manchester_internal_coll_type   custom
_manchester_internal_coll_frame_time 11s
_manchester_internal_coll_frame_width 1
_manchester_internal_coll_frame_method '\w scans'
_manchester_internal_coll_user   MP
_manchester_internal_coll_date   28/11/2014
_manchester_internal_process_user MP
_manchester_internal_process_date 02/12/2014
_manchester_internal_solution_user MP
_manchester_internal_solution_date 02/12/2014
_manchester_internal_refinement_user FO
_manchester_internal_refinement_date 21/07/2015
_manchester_internal_validation_user FO
_manchester_internal_validation_date 21/07/2015
_manchester_internal_archive_date 21/07/2015
_chemical_oxdiff_formula         Sm(C5H2(SiC3H9)3)2OC4H8
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 Secondary CH2 refined with riding coordinates:
 C29(H29A,H29B), C30(H30A,H30B), C31(H31A,H31B), C32(H32A,H32B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C17(H17), C19(H19)
2.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,
 H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C),
 C14(H14A,H14B,H14C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,
 H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C26(H26A,
 H26B,H26C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C)
;
_shelx_res_checksum              27567
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'