Total synthesis of conosilane A via a site-selective C-H functionalization strategy.
Yuan, Ziyun; Hu, Xiaojun; Zhang, Hao; Liu, Lin; Chen, Peng; He, Min; Xie, Xingang; Wang, Xiaolei; She, Xuegong; Chemical communications (Cambridge, England) 54 (2018) 912–915; doi:10.1039/c7cc09367e

data_7121065
_publ_section_title
;
 Total synthesis of conosilane A via a site-selective C-H
 functionalization strategy.
;
_journal_issue                   8
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              912
_journal_page_last               915
_journal_paper_doi               10.1039/c7cc09367e
_journal_volume                  54
_journal_year                    2018
_chemical_formula_moiety         'C15 H16 O5'
_chemical_formula_sum            'C15 H16 O5'
_chemical_formula_weight         276.28
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2017-11-15
_audit_creation_method
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Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
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_audit_update_record
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2017-11-23 deposited with the CCDC.
2018-01-02 downloaded from the CCDC.
;
_cell_angle_alpha                87.520(11)
_cell_angle_beta                 68.565(15)
_cell_angle_gamma                88.715(16)
_cell_formula_units_Z            4
_cell_length_a                   10.057(2)
_cell_length_b                   11.4810(18)
_cell_length_c                   12.6213(12)
_cell_measurement_reflns_used    614
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      19.9200
_cell_measurement_theta_min      3.6630
_cell_volume                     1355.2(4)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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_temperature      173.00(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -18.00   25.50   1.5000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  -99.0000 -120.0000 29

  2 omega   47.00  102.50   1.5000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  178.0000 -120.0000 37

  3 omega   17.00   47.00   1.5000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   57.0000    0.0000 20

  4 omega  -20.00   61.00   1.5000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -99.0000   60.0000 54

  5 omega  -51.00   88.50   1.5000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -19.0000 -120.0000 93

  6 omega    3.00   69.00   1.5000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   38.0000  -90.0000 44
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0741171000
_diffrn_orient_matrix_UB_12      0.0132614000
_diffrn_orient_matrix_UB_13      0.0213737000
_diffrn_orient_matrix_UB_21      -0.0151295000
_diffrn_orient_matrix_UB_22      -0.0576333000
_diffrn_orient_matrix_UB_23      -0.0100764000
_diffrn_orient_matrix_UB_31      -0.0042936000
_diffrn_orient_matrix_UB_32      -0.0180741000
_diffrn_orient_matrix_UB_33      0.0556052000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1009
_diffrn_reflns_av_unetI/netI     0.2350
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9272
_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         26.021
_diffrn_reflns_theta_min         3.357
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.32737
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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    1.354
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         5320
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.979
_refine_ls_R_factor_all          0.2400
_refine_ls_R_factor_gt           0.0862
_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^)+(0.0318P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1365
_refine_ls_wR_factor_ref         0.2114
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1757
_reflns_number_total             5320
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc09367e2.cif
_cod_data_source_block           yuanzy_1113
_cod_depositor_comments          'Adding full bibliography for 7121065.cif.'
_cod_original_cell_volume        1355.3(4)
_cod_database_code               7121065
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.78
_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 Ternary CH refined with riding coordinates:
 C2(H2), C4(H4), C17(H17), C19(H19)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C8(H8A,H8B), C10(H10A,H10B), C12(H12A,H12B), C18(H18A,H18B),
 C21(H21A,H21B), C25(H25A,H25B), C27(H27A,H27B)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C29(H29A,H29B,H29C), C30(H30A,H30B,
 H30C)
;
_shelx_res_checksum              70763
_olex2_date_sample_data_collection 2017-11-13
_olex2_submission_special_instructions 'No special instructions were received'