A solid acetylene reagent with enhanced reactivity: fluoride-mediated functionalization of alcohols and phenols
Werner, Georg; Rodygin, Konstantin S.; Kostin, Anton A.; Gordeev, Evgeniy G.; Kashin, Alexey S.; Ananikov, Valentine P.; Green Chem.  (2017) –; doi:10.1039/C7GC00724H

data_7228289
_publ_section_title
;
 A solid acetylene reagent with enhanced reactivity: fluoride-mediated
 functionalization of alcohols and phenols
;
_journal_name_full               'Green Chem.'
_journal_paper_doi               10.1039/C7GC00724H
_journal_year                    2017
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C29 H48 O'
_chemical_formula_sum            'C29 H48 O'
_chemical_formula_weight         412.67
_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
_audit_creation_date             2015-12-28
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2015-12-28 deposited with the CCDC.
2017-05-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 117.576(8)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.6051(8)
_cell_length_b                   8.5936(3)
_cell_length_c                   13.0034(8)
_cell_measurement_reflns_used    3089
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.6130
_cell_measurement_theta_min      3.6130
_cell_volume                     1248.55(15)
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -23.00   16.00   1.0000   22.3500
omega____ theta____ kappa____ phi______ frames
    -      -20.4081  -99.0000 -150.0000 39

  2 omega    0.00   89.00   1.0000   22.3500
omega____ theta____ kappa____ phi______ frames
    -       21.3456   57.0000   60.0000 89

  3 omega  -51.00   47.00   1.0000   22.3500
omega____ theta____ kappa____ phi______ frames
    -       21.3456  -38.0000   90.0000 98

  4 omega   22.00   50.00   1.0000   22.3500
omega____ theta____ kappa____ phi______ frames
    -      -20.4081   77.0000  150.0000 28

  5 omega  -13.00   59.00   1.0000   22.3500
omega____ theta____ kappa____ phi______ frames
    -       21.3456  -99.0000 -120.0000 72

  6 omega   13.00   65.00   1.0000   22.3500
omega____ theta____ kappa____ phi______ frames
    -       21.3456   57.0000 -180.0000 52

  7 omega   27.00   53.00   1.0000   22.3500
omega____ theta____ kappa____ phi______ frames
    -       21.3456   57.0000  -60.0000 26
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0623932000
_diffrn_orient_matrix_UB_12      0.0122391000
_diffrn_orient_matrix_UB_13      0.0215627000
_diffrn_orient_matrix_UB_21      0.0066400000
_diffrn_orient_matrix_UB_22      0.0074469000
_diffrn_orient_matrix_UB_23      0.0569651000
_diffrn_orient_matrix_UB_31      0.0099864000
_diffrn_orient_matrix_UB_32      -0.0812655000
_diffrn_orient_matrix_UB_33      0.0084828000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_unetI/netI     0.0568
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_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       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10184
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.491
_diffrn_reflns_theta_min         2.957
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.063
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94926
_exptl_absorpt_correction_type   multi-scan
_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)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.098
_exptl_crystal_description       needle
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Refined as a perfect inversion twin.
;
_refine_ls_abs_structure_Flack   0.5
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         5695
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0426
_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^)+(0.0428P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0855
_refine_ls_wR_factor_ref         0.0929
_reflns_Friedel_coverage         0.875
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                4853
_reflns_number_total             5695
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7gc00724h2.cif
_cod_data_source_block           rks-1
_cod_original_cell_volume        1248.56(14)
_cod_database_code               7228289
_chemical_oxdiff_formula         'C29 H48 O'
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.50
_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:
 C3(H3), C8(H8), C9(H9), C14(H14), C17(H17), C20(H20), C25(H25)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C4(H4A,H4B), C7(H7A,H7B), C11(H11A,H11B), C12(H12A,
 H12B), C15(H15A,H15B), C16(H16A,H16B), C22(H22A,H22B), C23(H23A,H23B),
 C24(H24A,H24B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C28(H28)
2.d X=CH2 refined with riding coordinates:
 C29(H29A,H29B)
2.e Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C21(H21A,H21B,H21C), C26(H26A,H26B,
 H26C), C27(H27A,H27B,H27C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'