Development and Application of O-(Trimethylsilyl)aryl Fluorosulfates for the Synthesis of Arynes.
Chen, Qiao; Yu, Hongmei; Xu, Zhaoqing; Lin, Li; Jiang, Xianxing; Wang, Rui; The Journal of organic chemistry 80 (2015) 6890–6896; doi:10.1021/acs.joc.5b00923

data_4031134
_publ_section_title
;
 Development and Application of O-(Trimethylsilyl)aryl Fluorosulfates for
 the Synthesis of Arynes.
;
_journal_issue                   13
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6890
_journal_page_last               6896
_journal_paper_doi               10.1021/acs.joc.5b00923
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C22 H23 F O3 S Si'
_chemical_formula_sum            'C22 H23 F O3 S Si'
_chemical_formula_weight         414.55
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-03-11
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                91.882(6)
_cell_angle_beta                 95.119(5)
_cell_angle_gamma                93.892(5)
_cell_formula_units_Z            4
_cell_length_a                   9.5146(5)
_cell_length_b                   10.4175(8)
_cell_length_c                   22.0011(16)
_cell_measurement_reflns_used    2642
_cell_measurement_temperature    293
_cell_measurement_theta_max      22.3580
_cell_measurement_theta_min      3.8640
_cell_volume                     2165.3(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega   -3.00   82.20   1.2000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854   38.0000   60.0000 71

  2 omega   -5.00   22.60   1.2000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1479  -99.0000 -120.0000 23

  3 omega  -17.00   10.60   1.2000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1479  -99.0000   30.0000 23

  4 omega  -18.00   49.20   1.2000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -77.0000  120.0000 56

  5 omega  -20.00   14.80   1.2000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1479  -99.0000 -150.0000 29

  6 omega  -43.00   65.00   1.2000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -19.0000 -150.0000 90

  7 omega   36.00   85.20   1.2000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  178.0000  -90.0000 41
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0138848000
_diffrn_orient_matrix_UB_12      -0.0347516000
_diffrn_orient_matrix_UB_13      0.0262573000
_diffrn_orient_matrix_UB_21      0.0326886000
_diffrn_orient_matrix_UB_22      -0.0533918000
_diffrn_orient_matrix_UB_23      -0.0119005000
_diffrn_orient_matrix_UB_31      0.0661002000
_diffrn_orient_matrix_UB_32      0.0246191000
_diffrn_orient_matrix_UB_33      0.0147734000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0496
_diffrn_reflns_av_unetI/netI     0.1021
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            15468
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.35
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.232
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76390
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
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    1.272
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     511
_refine_ls_number_reflns         8506
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.1422
_refine_ls_R_factor_gt           0.0732
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0769P)^2^+0.3814P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1572
_refine_ls_wR_factor_ref         0.2154
_reflns_number_gt                4379
_reflns_number_total             8506
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b00923_si_001.cif
_cod_data_source_block           chenqiao0309
_cod_depositor_comments          'Adding full bibliography for 4031134.cif.'
_cod_original_cell_volume        2165.4(3)
_cod_database_code               4031134
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11),
 C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C24(H24), C25(H25), C26(H26),
  C27(H27), C28(H28), C30(H30), C31(H31), C32(H32), C33(H33), C34(H34),
 C36(H36), C37(H37), C38(H38), C39(H39)
2.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C42(H42A,H42B,
 H42C), C43(H43A,H43B,H43C), C44(H44A,H44B,H44C)
;
_olex2_date_sample_data_collection 2015-03-11
_olex2_submission_special_instructions 'No special instructions were received'