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_7155629
_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         'C18 H14 O4'
_chemical_formula_sum            'C18 H14 O4'
_chemical_formula_weight         294.29
_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             2016-07-03
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 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                 106.1392(19)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.9896(4)
_cell_length_b                   7.31234(10)
_cell_length_c                   20.2663(4)
_cell_measurement_reflns_used    25466
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      73.6080
_cell_measurement_theta_min      4.4400
_cell_volume                     2845.59(9)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43d (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 5.3046
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_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    -66.00  33.00   1.00    1.00    --  -41.82  37.00 -30.00   99
  2  \w   -130.00  46.00   1.00    1.00    --  -41.82   0.00 150.00  176
  3  \w     23.00  98.00   1.00    1.00    --   41.82-125.00  60.00   75
  4  \w     23.00  98.00   1.00    1.00    --   41.82-125.00 -60.00   75
  5  \w     34.00 133.00   1.00    4.00    --  107.00 -45.00-180.00   99
  6  \w     33.00 131.00   1.00    4.00    --  107.00 -37.00  73.00   98
  7  \w     31.00 140.00   1.00    4.00    --  107.00 -77.00   0.00  109
  8  \w     24.00 109.00   1.00    4.00    --  107.00 -94.00  90.00   85
  9  \w     34.00 121.00   1.00    4.00    --  107.00-125.00   0.00   87
 10  \w     54.00 178.00   1.00    4.00    --  107.00  15.00  90.00  124
 11  \w     74.00 178.00   1.00    4.00    --  107.00  77.00-120.00  104
 12  \w     31.00 135.00   1.00    4.00    --  107.00 -30.00 -90.00  104
 13  \w     27.00 111.00   1.00    4.00    --  107.00-100.00-133.00   84
 14  \w   -118.00  -9.00   1.00    1.00    --  -41.82 -77.00 120.00  109
 15  \w   -114.00 -14.00   1.00    1.00    --  -41.82 -57.00-180.00  100
 16  \w   -114.00 -14.00   1.00    1.00    --  -41.82 -57.00   0.00  100
 17  \w   -118.00  -9.00   1.00    1.00    --  -41.82 -77.00 -90.00  109
 18  \w     74.00 178.00   1.00    4.00    --  107.00  77.00 -90.00  104
 19  \w     78.00 178.00   1.00    4.00    --  107.00  61.00-150.00  100
 20  \w     79.00 178.00   1.00    4.00    --  107.00  30.00-180.00   99
 21  \w     74.00 178.00   1.00    4.00    --  107.00  77.00  30.00  104
 22  \w     79.00 178.00   1.00    4.00    --  107.00  30.00 -30.00   99
 23  \w     78.00 178.00   1.00    4.00    --  107.00  61.00-180.00  100
 24  \w     74.00 178.00   1.00    4.00    --  107.00  77.00 -30.00  104
 25  \w     74.00 178.00   1.00    4.00    --  107.00  77.00  90.00  104
 26  \w    -70.00  31.00   1.00    1.00    --  -41.82  57.00-150.00  101
 27  \w   -118.00  -9.00   1.00    1.00    --  -41.82 -77.00  60.00  109
 28  \w   -118.00  -9.00   1.00    1.00    --  -41.82 -77.00-180.00  109
 29  \w   -118.00  -9.00   1.00    1.00    --  -41.82 -77.00   0.00  109
 30  \w     74.00 178.00   1.00    4.00    --  107.00  77.00  60.00  104
 31  \w     74.00 178.00   1.00    4.00    --  107.00  77.00 120.00  104
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0590079000
_diffrn_orient_matrix_UB_12      0.0348393000
_diffrn_orient_matrix_UB_13      0.0337667000
_diffrn_orient_matrix_UB_21      -0.0260237000
_diffrn_orient_matrix_UB_22      -0.1975675000
_diffrn_orient_matrix_UB_23      -0.0166970000
_diffrn_orient_matrix_UB_31      0.0477289000
_diffrn_orient_matrix_UB_32      -0.0643491000
_diffrn_orient_matrix_UB_33      0.0695839000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1165
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            51643
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.674
_diffrn_reflns_theta_min         4.486
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.799
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43944
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43d (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    1.374
_exptl_crystal_description       block
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     399
_refine_ls_number_reflns         5691
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.125
_refine_ls_R_factor_all          0.0697
_refine_ls_R_factor_gt           0.0670
_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^)+(0.0417P)^2^+8.7778P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1826
_refine_ls_wR_factor_ref         0.1841
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5302
_reflns_number_total             5691
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob00991g2.cif
_cod_data_source_block           mw10
_cod_original_cell_volume        2845.58(9)
_cod_database_code               7155629
_chemical_oxdiff_formula         'C20 H20 O4'
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_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 Secondary CH2 refined with riding coordinates:
 C209(H20D,H20E), C212(H21A,H21B), C109(H10D,H10E), C112(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C205(H205), C206(H206), C215(H215), C216(H216), C217(H217), C218(H218),
 C221(H221), C105(H105), C106(H106), C115(H115), C116(H116), C117(H117),
 C118(H118), C121(H121)
2.c Idealised Me refined as rotating group:
 C201(H20A,H20B,H20C), C101(H10A,H10B,H10C)
;
_shelx_res_checksum              1642
_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 3.410
_oxdiff_exptl_absorpt_empirical_full_min 0.365