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_7155630
_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_formula_moiety         'C16 H16 O2'
_chemical_formula_sum            'C16 H16 O2'
_chemical_formula_weight         240.29
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-03-23
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.16 svn.r3265 for OlexSys, GUI svn.r5155)
;
_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                90
_cell_formula_units_Z            4
_cell_length_a                   15.81826(15)
_cell_length_b                   9.23296(10)
_cell_length_c                   8.32936(9)
_cell_measurement_reflns_used    5956
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      77.9170
_cell_measurement_theta_min      5.3140
_cell_volume                     1216.50(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2833
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -116.00 -17.00   1.00    1.00    --  -41.71 -38.00   0.00   99
  2  \w     18.00  98.00   1.00    1.00    --   41.71-125.00  60.00   80
  3  \w    100.00 178.00   1.00    4.00    --  114.00 111.00 -60.00   78
  4  \w    100.00 178.00   1.00    4.00    --  114.00 111.00   0.00   78
  5  \w     85.00 178.00   1.00    4.00    --  114.00  61.00 120.00   93
  6  \w     32.00 109.00   1.00    4.00    --  114.00 -95.00 120.00   77
  7  \w     38.00 116.00   1.00    4.00    --  114.00-111.00-120.00   78
  8  \w     86.00 178.00   1.00    4.00    --  114.00  30.00-180.00   92
  9  \w   -115.00 -14.00   1.00    1.00    --  -41.71 -57.00 -90.00  101
 10  \w   -118.00  -9.00   1.00    1.00    --  -41.71 -77.00 150.00  109
 11  \w     -4.00  83.00   1.00    1.00    --   41.71 -99.00 150.00   87
 12  \w     38.00 147.00   1.00    4.00    --  114.00 -77.00 -60.00  109
 13  \w     81.00 178.00   1.00    4.00    --  114.00  77.00  60.00   97
 14  \w     86.00 178.00   1.00    4.00    --  114.00  30.00   0.00   92
 15  \w     85.00 178.00   1.00    4.00    --  114.00  61.00 -60.00   93
 16  \w     85.00 110.00   1.00    4.00    --  114.00  61.00-150.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0728392000
_diffrn_orient_matrix_UB_12      -0.1051419000
_diffrn_orient_matrix_UB_13      -0.0386359000
_diffrn_orient_matrix_UB_21      0.0491588000
_diffrn_orient_matrix_UB_22      -0.1241992000
_diffrn_orient_matrix_UB_23      0.0807608000
_diffrn_orient_matrix_UB_31      -0.0419259000
_diffrn_orient_matrix_UB_32      0.0368569000
_diffrn_orient_matrix_UB_33      0.1619084000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0147
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            9414
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.260
_diffrn_reflns_theta_min         5.548
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.676
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68388
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
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    1.312
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.0072(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     83
_refine_ls_number_reflns         1299
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0370
_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^)+(0.0591P)^2^+0.2644P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1057
_refine_ls_wR_factor_ref         0.1068
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1242
_reflns_number_total             1299
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob00991g2.cif
_cod_data_source_block           mw9
_cod_database_code               7155630
_chemical_oxdiff_formula         'C20 H20 O2'
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C2(H2), C4(H4), C3(H3)
;
_shelx_res_checksum              20944
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.275
_oxdiff_exptl_absorpt_empirical_full_min 0.833