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_7125176
_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         'C17 H22 O2'
_chemical_formula_sum            'C17 H22 O2'
_chemical_formula_weight         258.34
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-07-21
_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                91.758(11)
_cell_angle_beta                 94.311(12)
_cell_angle_gamma                110.931(13)
_cell_formula_units_Z            4
_cell_length_a                   8.9679(13)
_cell_length_b                   11.9038(16)
_cell_length_c                   14.801(2)
_cell_measurement_reflns_used    1237
_cell_measurement_temperature    150.01(11)
_cell_measurement_theta_max      20.8510
_cell_measurement_theta_min      3.6780
_cell_volume                     1468.8(4)
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.01(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0714
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -86.00    9.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.7663  -19.0000  -60.0000 95

  2 omega  -83.00   12.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.7663  -77.0000  120.0000 95

  3 omega  -26.00   -1.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.7663  -57.0000 -120.0000 25

  4 omega  -45.00   50.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.7663   77.0000 -120.0000 95

  5 omega   19.00   61.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8601  -99.0000   30.0000 42
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0148640000
_diffrn_orient_matrix_UB_12      -0.0547417000
_diffrn_orient_matrix_UB_13      0.0217316000
_diffrn_orient_matrix_UB_21      -0.0819040000
_diffrn_orient_matrix_UB_22      -0.0071577000
_diffrn_orient_matrix_UB_23      0.0005780000
_diffrn_orient_matrix_UB_31      -0.0174143000
_diffrn_orient_matrix_UB_32      -0.0322117000
_diffrn_orient_matrix_UB_33      -0.0429621000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0602
_diffrn_reflns_av_unetI/netI     0.1702
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9199
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.348
_diffrn_reflns_theta_min         3.413
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65849
_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.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.168
_exptl_crystal_description       needle
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.3016
_exptl_crystal_size_mid          0.0733
_exptl_crystal_size_min          0.0455
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     366
_refine_ls_number_reflns         5365
_refine_ls_number_restraints     315
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.1904
_refine_ls_R_factor_gt           0.0816
_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^)+(0.0620P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1566
_refine_ls_wR_factor_ref         0.2048
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2450
_reflns_number_total             5365
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc07318b2.cif
_cod_data_source_block           1a
_cod_database_code               7125176
_manchester_internal_coll_name   adpm149
_manchester_internal_coll_client MP/DJP/DPM
_manchester_internal_coll_type   custom
_manchester_internal_coll_frame_time 4.675s
_manchester_internal_coll_frame_width 1
_manchester_internal_coll_frame_method '\w scans'
_manchester_internal_coll_user   MP
_manchester_internal_coll_date   23/05/2015
_manchester_internal_process_user FO
_manchester_internal_process_date 20/07/2015
_manchester_internal_solution_user FO
_manchester_internal_solution_date 20/07/2015
_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         C17H22O2
_reflns_odcompleteness_completeness 99.77
_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, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C4-C5 \\sim C4A-C5
 with sigma of 0.02
 C4A-C3A \\sim C4-C3
 with sigma of 0.02
 C2-C3A \\sim C3-C2
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(H2BC)=Sof(H2BD)=Sof(C3)=Sof(H3A)=Sof(H3B)=Sof(C4)=Sof(H4A)=Sof(H4B)=1-
 FVAR(1)
 Sof(H2AA)=Sof(H2AB)=Sof(C3A)=Sof(H3AA)=Sof(H3AB)=Sof(C4A)=Sof(H4AA)=Sof(H4AB)=
 FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C6(H6), C9(H9), C23(H23), C26(H26)
5.b Secondary CH2 refined with riding coordinates:
 C2(H2AA,H2AB), C2(H2BC,H2BD), C3A(H3AA,H3AB), C4A(H4AA,H4AB), C3(H3A,H3B),
 C4(H4A,H4B), C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B)
5.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17), C24(H24), C30(H30),
 C31(H31), C32(H32), C33(H33), C34(H34)
5.d X=CH2 refined with riding coordinates:
 C8(H8A,H8B), C25(H25A,H25B)
5.e Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C27(H27A,H27B,H27C), C28(H28A,H28B,
 H28C)
;
_shelx_res_checksum              72100
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'