Silver salts and DBU cooperatively catalyzed nucleophilic addition/cyclization of propargylic alcohols with trifluoromethyl ketones.
Wang, Jingjing; Kong, Wei-Guang; Li, Feng; Liu, Jie; Shen, Qin; Liu, Lantao; Zhao, Wen-Xian; Organic & biomolecular chemistry 13 (2015) 5399–5406; doi:10.1039/c5ob00438a

data_7154418
_publ_section_title
;
 Silver salts and DBU cooperatively catalyzed nucleophilic
 addition/cyclization of propargylic alcohols with trifluoromethyl
 ketones.
;
_journal_issue                   19
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5399
_journal_page_last               5406
_journal_paper_doi               10.1039/c5ob00438a
_journal_volume                  13
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H16 F4 O2'
_chemical_formula_sum            'C19 H16 F4 O2'
_chemical_formula_weight         352.32
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-01-07
_audit_creation_method
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Olex2 1.2
(compiled 2014.12.26 svn.r3119 for OlexSys, GUI svn.r4975)
;
_audit_update_record
;
2015-01-25 deposited with the CCDC.
2015-04-02 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.7578(4)
_cell_length_b                   10.8532(6)
_cell_length_c                   18.2457(9)
_cell_measurement_reflns_used    3765
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      71.8090
_cell_measurement_theta_min      4.7270
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_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
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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)'
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_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      291.15
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_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -66.00  -32.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000 -120.0000 34

  2 omega  -77.00  -52.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000 -150.0000 25

  3 omega  -77.00  -44.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000  120.0000 33

  4 omega  -77.00  -44.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000  -60.0000 33

  5 omega  -13.00   65.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -77.0000  150.0000 78

  6 omega   78.00  104.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  160.0000   30.0000 26

  7 omega   77.00  120.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   77.0000  150.0000 43

  8 omega   27.00   57.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   77.0000  150.0000 30

  9 omega   23.00  111.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000 -125.0000   30.0000 88

 10 omega   59.00   90.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000   30.0000 31

 11 omega   41.00   98.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  -90.0000 57

 12 omega   45.00   98.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000    0.0000 53

 13 omega   41.00  103.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000   30.0000 62

 14 omega   48.00   84.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000 -150.0000 36

 15 omega   51.00   88.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000 -150.0000 37

 16 omega   49.00   86.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000  -30.0000 37

 17 omega   39.00  152.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000    0.0000 -150.0000 113

 18 omega  -30.00   70.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000    0.0000 100

 19 omega  -69.00   21.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000 -120.0000 90

 20 omega  105.00  131.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -12.0000  120.0000 26

 21 omega   41.00   88.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -25.0000   60.0000 47

 22 omega   95.00  123.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -63.0000 -180.0000 28

 23 omega   52.00   86.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -37.0000  120.0000 34

 24 omega  125.00  164.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000  -90.0000 39

 25 omega   67.00   92.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -63.0000  -60.0000 25

 26 omega   44.00   72.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   12.0000  -60.0000 28

 27 omega   92.00  162.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   12.0000  -60.0000 70

 28 omega  105.00  131.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   50.0000   60.0000 26

 29 omega  152.00  178.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   50.0000   60.0000 26

 30 omega   51.00   77.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000  150.0000 26

 31 omega   85.00  110.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000  150.0000 25

 32 omega   40.00   65.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -37.0000   90.0000 25

 33 omega   51.00   77.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000 -120.0000 26

 34 omega   74.00  118.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -11.0000   87.7833 44
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0520060000
_diffrn_orient_matrix_UB_12      0.0080788000
_diffrn_orient_matrix_UB_13      -0.0805260000
_diffrn_orient_matrix_UB_21      -0.1310549000
_diffrn_orient_matrix_UB_22      -0.0866590000
_diffrn_orient_matrix_UB_23      -0.0225475000
_diffrn_orient_matrix_UB_31      -0.1050760000
_diffrn_orient_matrix_UB_32      0.1121908000
_diffrn_orient_matrix_UB_33      -0.0116898000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10669
_diffrn_reflns_theta_full        72.32
_diffrn_reflns_theta_max         72.32
_diffrn_reflns_theta_min         4.74
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.996
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88928
_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_density_diffrn    1.349
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.06(17)
_refine_ls_extinction_coef       0.0166(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3423
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0390
_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^)+(0.0433P)^2^+0.1340P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0970
_refine_ls_wR_factor_ref         0.1014
_reflns_number_gt                3067
_reflns_number_total             3423
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ob00438a2.cif
_cod_data_source_block           20150104
_cod_depositor_comments          'Adding full bibliography for 7154418.cif.'
_cod_original_cell_volume        1734.27(15)
_cod_database_code               7154418
_chemical_oxdiff_formula         C20H20N4O4F6
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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), C7(H7), C12(H12), C13(H13), C15(H15),
 C16(H16)
2.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_olex2_submission_special_instructions 'No special instructions were received'