TfOH- and HBF<sub>4</sub>-Mediated Formal Cycloisomerizations and [4+3] Cycloadditions of Allene-alkynylbenzenes.
Xiang, Yu; Li, Zining; Wang, Lu-Ning; Yu, Zhi-Xiang; The Journal of organic chemistry 83 (2018) 7633–7647; doi:10.1021/acs.joc.8b00393

data_4035569
_publ_section_title
;
 TfOH- and HBF<sub>4</sub>-Mediated Formal Cycloisomerizations and [4+3]
 Cycloadditions of Allene-alkynylbenzenes.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7633
_journal_page_last               7647
_journal_paper_doi               10.1021/acs.joc.8b00393
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C22 H24 F N O2 S'
_chemical_formula_sum            'C22 H24 F N O2 S'
_chemical_formula_weight         385.48
_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
_audit_creation_date             2016-03-06
_audit_creation_method
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Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                72.602(9)
_cell_angle_beta                 87.821(10)
_cell_angle_gamma                87.697(10)
_cell_formula_units_Z            2
_cell_length_a                   6.2637(9)
_cell_length_b                   11.6536(11)
_cell_length_c                   13.7124(15)
_cell_measurement_reflns_used    1813
_cell_measurement_temperature    180.01(10)
_cell_measurement_theta_max      26.9080
_cell_measurement_theta_min      3.5880
_cell_volume                     954.0(2)
_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
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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_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)'
_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      180.01(10)
_diffrn_detector_area_resol_mean 5.1957
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details
;
  1 omega  -58.00   35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       10.8579  -57.0000   60.0000 93

  2 omega  -20.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       10.8579  -99.0000  -30.0000 73

  3 omega  -16.00   79.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       10.8579   57.0000 -150.0000 95
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0210731000
_diffrn_orient_matrix_UB_12      -0.0626458000
_diffrn_orient_matrix_UB_13      0.0099299000
_diffrn_orient_matrix_UB_21      -0.1077574000
_diffrn_orient_matrix_UB_22      -0.0077759000
_diffrn_orient_matrix_UB_23      -0.0102149000
_diffrn_orient_matrix_UB_31      0.0282420000
_diffrn_orient_matrix_UB_32      0.0093338000
_diffrn_orient_matrix_UB_33      -0.0523225000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0754
_diffrn_reflns_av_unetI/netI     0.1044
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5923
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_min         3.256
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.22458
_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
;
;
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.522
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3730
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.1100
_refine_ls_R_factor_gt           0.0727
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0763P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1574
_refine_ls_wR_factor_ref         0.1979
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2256
_reflns_number_total             3730
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00393_si_002.cif
_cod_data_source_block           exp_6671
_cod_original_cell_volume        954.01(19)
_cod_database_code               4035569
_shelxl_version_number           2014-3
_chemical_oxdiff_formula         'C21 N1 O2 S1 F1'
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.981
_reflns_odcompleteness_completeness 99.20
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.97
_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:
 C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C17(H17), C18(H18), C20(H20), C21(H21)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C22(H22A,H22B,H22C)
;
_olex2_submission_special_instructions 'No special instructions were received'