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_4035568
_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 H23 Cl F N O2 S'
_chemical_formula_sum            'C22 H23 Cl F N O2 S'
_chemical_formula_weight         419.92
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-02-18
_audit_creation_method
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Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
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_cell_angle_alpha                90
_cell_angle_beta                 91.811(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.142(3)
_cell_length_b                   8.359(2)
_cell_length_c                   12.4889(17)
_cell_measurement_reflns_used    1026
_cell_measurement_temperature    180.00(10)
_cell_measurement_theta_max      21.1750
_cell_measurement_theta_min      3.4480
_cell_volume                     2101.7(7)
_computing_cell_refinement
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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_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      180.00(10)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
  1 omega  -68.00   43.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       10.7017  -77.0000 -120.0000 111

  2 omega  -38.00   22.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.7954   38.0000 -180.0000 60
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0107427000
_diffrn_orient_matrix_UB_12      0.0760503000
_diffrn_orient_matrix_UB_13      -0.0189709000
_diffrn_orient_matrix_UB_21      0.0075936000
_diffrn_orient_matrix_UB_22      0.0336298000
_diffrn_orient_matrix_UB_23      0.0510658000
_diffrn_orient_matrix_UB_31      0.0326682000
_diffrn_orient_matrix_UB_32      0.0170068000
_diffrn_orient_matrix_UB_33      -0.0161891000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0723
_diffrn_reflns_av_unetI/netI     0.1389
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8145
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.020
_diffrn_reflns_theta_min         3.036
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.307
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54223
_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    1.327
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.436
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         4133
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.1448
_refine_ls_R_factor_gt           0.0626
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0158P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0905
_refine_ls_wR_factor_ref         0.1249
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2063
_reflns_number_total             4133
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00393_si_001.cif
_cod_data_source_block           exp_6623
_cod_original_cell_volume        2101.8(7)
_cod_database_code               4035568
_shelxl_version_number           2014-3
_chemical_oxdiff_formula         'C20 H18 N2 O1'
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.970
_reflns_odcompleteness_completeness 99.22
_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:
 C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C10(H10), C11(H11), C12(H12), 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'