Metal-free cycloisomerizations of o-alkynylbiaryls.
Zhang, Jingyi; Li, Siqi; Qiao, Yan; Peng, Cheng; Wang, Xiao-Na; Chang, Junbiao; Chemical communications (Cambridge, England) 54 (2018) 12455–12458; doi:10.1039/c8cc05484c

data_7122450
_publ_section_title
;
 Metal-free cycloisomerizations of o-alkynylbiaryls.
;
_journal_issue                   88
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              12455
_journal_page_last               12458
_journal_paper_doi               10.1039/c8cc05484c
_journal_volume                  54
_journal_year                    2018
_chemical_formula_moiety         'C32 H25 N O2 S'
_chemical_formula_sum            'C32 H25 N O2 S'
_chemical_formula_weight         487.59
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-09-04
_audit_creation_method
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Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
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_audit_update_record
;
2018-06-05 deposited with the CCDC.
2018-10-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.558(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.6386(4)
_cell_length_b                   19.7299(5)
_cell_length_c                   12.6060(4)
_cell_measurement_reflns_used    2935
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.5430
_cell_measurement_theta_min      4.2620
_cell_volume                     2561.03(15)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega -108.00  -69.00   0.5000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000 -120.0000 78

  2 omega -102.00  -68.00   0.5000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000   60.0000 68

  3 omega  -65.00  -16.00   0.5000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000   60.0000 98

  4 omega   -1.00   33.00   0.5000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   19.0000  150.0000 68

  5 omega   42.00  102.00   0.5000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   19.0000  150.0000 120

  6 omega   57.00  109.00   0.5000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000    0.0000 104

  7 omega    3.00   76.00   0.5000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000   90.0000 146

  8 omega   63.00   88.00   0.5000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000   90.0000 50

  9 omega   51.00   97.00   0.5000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000  -90.0000 92

 10 omega   40.00   67.00   0.5000   27.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -60.0000 54

 11 omega   47.00   96.00   0.5000   27.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   60.0000 98

 12 omega   39.00   96.00   0.5000   27.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -60.0000 114

 13 omega   37.00   85.00   0.5000   27.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   30.0000 96

 14 omega   60.00   90.00   0.5000   27.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 60

 15 omega   59.00   85.00   0.5000   27.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000   30.0000 52

 16 omega   92.00  172.00   0.5000   27.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   30.0000 160

 17 omega   42.00   86.00   0.5000   27.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 88

 18 omega  119.00  144.00   0.5000   27.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000   30.0000 50

 19 omega  137.00  170.00   0.5000   27.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000    0.0000 66

 20 omega   51.00   98.00   0.5000   27.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -30.0000 94

 21 omega   90.00  161.00   0.5000   27.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   60.0000 142
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0936536000
_diffrn_orient_matrix_UB_12      0.0515716000
_diffrn_orient_matrix_UB_13      0.0305133000
_diffrn_orient_matrix_UB_21      -0.1085882000
_diffrn_orient_matrix_UB_22      -0.0537663000
_diffrn_orient_matrix_UB_23      -0.0229799000
_diffrn_orient_matrix_UB_31      0.0425565000
_diffrn_orient_matrix_UB_32      -0.0234304000
_diffrn_orient_matrix_UB_33      0.1203716000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10153
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.075
_diffrn_reflns_theta_max         67.075
_diffrn_reflns_theta_min         4.260
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.350
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80782
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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    1.265
_exptl_crystal_description       prism
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         4566
_refine_ls_number_restraints     19
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0829
_refine_ls_R_factor_gt           0.0615
_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^)+(0.1063P)^2^+0.2073P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1815
_refine_ls_wR_factor_ref         0.2051
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3127
_reflns_number_total             4566
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc05484c4.cif
_cod_data_source_block           201708150
_cod_depositor_comments          'Adding full bibliography for 7122450.cif.'
_cod_original_cell_volume        2561.03(14)
_cod_database_code               7122450
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C38H41N2O6S1
_shelx_estimated_absorpt_t_max   0.877
_shelx_estimated_absorpt_t_min   0.774
_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, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C25, C24
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3. Uiso/Uaniso restraints and constraints
Uanis(C24) \\sim Ueq, Uanis(C23) \\sim Ueq, Uanis(C22) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
4.a Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B)
4.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C7(H7), C8(H8), C12(H12), C15(H15), C16(H16),
 C17(H17), C18(H18), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25), C27(H27),
  C28(H28), C30(H30), C31(H31)
4.c Idealised Me refined as rotating group:
 C32(H32A,H32B,H32C)
;
_olex2_submission_special_instructions 'No special instructions were received'