Strained alkynes derived from 2,2′-dihydroxy-1,1′-biaryls; synthesis and copper-free cycloaddition with azides
Del Grosso, Alessandro; Galanopoulos, Lavrentis-Dimitrios; Chiu, Cookson K. C.; Clarkson, Guy J.; O′ Connor, Peter B.; Wills, Martin; Org. Biomol. Chem.  (2017) –; doi:10.1039/C7OB00991G

data_7155635
_publ_section_title
;
 Strained alkynes derived from 2,2&#x2032;-dihydroxy-1,1&#x2032;-biaryls;
 synthesis and copper-free cycloaddition with azides
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB00991G
_journal_year                    2017
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C24 H16 O2'
_chemical_formula_sum            'C24 H16 O2'
_chemical_formula_weight         336.37
_space_group_crystal_system      hexagonal
_space_group_IT_number           169
_space_group_name_Hall           'P 61'
_space_group_name_H-M_alt        'P 61'
_symmetry_space_group_name_Hall  'P 61'
_symmetry_space_group_name_H-M   'P 61'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-07-22
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3151 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2016-11-04 deposited with the CCDC.
2017-05-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            18
_cell_length_a                   13.54378(8)
_cell_length_b                   13.54378(8)
_cell_length_c                   48.3660(3)
_cell_measurement_reflns_used    28020
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      77.7950
_cell_measurement_theta_min      3.6410
_cell_volume                     7683.35(8)
_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
'CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01)'
_computing_data_reduction
'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, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1417
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -49.00   32.00   0.7500   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.7109   38.0000   60.0000 108

  2 omega  -96.00    3.00   0.7500   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.7109  125.0000 -150.0000 132

  3 omega -111.00  -81.75   0.7500   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.7109  -57.0000  -30.0000 39

  4 omega  -38.00   26.50   0.7500   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.7109   38.0000    0.0000 86

  5 omega -115.00  -16.00   0.7500   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.7109  -57.0000  -90.0000 132

  6 omega  -70.00  -16.00   0.7500   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.7109  -57.0000  -30.0000 72

  7 omega   38.00   82.25   0.7500   80.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -30.0000 -150.0000 59

  8 omega   41.00   96.50   0.7500   80.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -45.0000  120.0000 74

  9 omega   89.00  146.00   0.7500   80.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -77.0000  -60.0000 76

 10 omega   39.50  116.00   0.7500   80.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000 -111.0000  120.0000 102

 11 omega   41.00   90.50   0.7500   80.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -30.0000   60.0000 66

 12 omega   87.00  167.25   0.7500   80.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000   61.0000 -120.0000 107

 13 omega   94.00  178.00   0.7500   80.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000   45.0000   30.0000 112

 14 omega  112.00  166.00   0.7500   80.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  111.0000   90.0000 72

 15 omega   54.50   92.00   0.7500   80.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000 -111.0000  -60.0000 50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0618576000
_diffrn_orient_matrix_UB_12      0.0213464000
_diffrn_orient_matrix_UB_13      -0.0239960000
_diffrn_orient_matrix_UB_21      0.0452656000
_diffrn_orient_matrix_UB_22      -0.0558343000
_diffrn_orient_matrix_UB_23      -0.0202768000
_diffrn_orient_matrix_UB_31      -0.1066615000
_diffrn_orient_matrix_UB_32      -0.1169032000
_diffrn_orient_matrix_UB_33      0.0053029000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       60
_diffrn_reflns_limit_l_min       -59
_diffrn_reflns_number            42875
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.962
_diffrn_reflns_theta_min         3.655
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.650
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.35792
_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. 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    1.309
_exptl_crystal_description       block
_exptl_crystal_F_000             3168
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 4938 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     704
_refine_ls_number_reflns         10592
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0318
_refine_ls_R_factor_gt           0.0315
_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^)+(0.0636P)^2^+0.1283P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0829
_refine_ls_wR_factor_ref         0.0830
_reflns_Friedel_coverage         0.970
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                10491
_reflns_number_total             10592
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob00991g2.cif
_cod_data_source_block           adg1
_cod_original_cell_volume        7683.33(10)
_cod_database_code               7155635
_chemical_oxdiff_formula         'C20 H20 O2'
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.3330(14) 0.6670(14)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3.a Secondary CH2 refined with riding coordinates:
 C302(H30A,H30B), C305(H30C,H30D), C202(H20A,H20B), C205(H20C,H20D), C102(H10A,
 H10B), C105(H10C,H10D)
3.b Aromatic/amide H refined with riding coordinates:
 C308(H308), C309(H309), C311(H311), C312(H312), C313(H313), C314(H314),
 C319(H319), C320(H320), C321(H321), C322(H322), C324(H324), C325(H325),
 C208(H208), C209(H209), C211(H211), C212(H212), C213(H213), C214(H214),
 C219(H219), C220(H220), C221(H221), C222(H222), C224(H224), C225(H225),
 C108(H108), C109(H109), C111(H111), C112(H112), C113(H113), C114(H114),
 C119(H119), C120(H120), C121(H121), C122(H122), C124(H124), C125(H125)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'