Synthesis and cycloaddition reactions of strained alkynes derived from 2,2'-dihydroxy-1,1'-biaryls.
Mistry, Anish; Knighton, Richard C.; Forshaw, Sam; Dualeh, Zakaria; Parker, Jeremy S.; Wills, Martin; Organic & biomolecular chemistry 16 (2018) 8965–8975; doi:10.1039/c8ob01768a

data_7156565
_publ_section_title
;
 Synthesis and cycloaddition reactions of strained alkynes derived from
 2,2'-dihydroxy-1,1'-biaryls.
;
_journal_issue                   46
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8965
_journal_page_last               8975
_journal_paper_doi               10.1039/c8ob01768a
_journal_volume                  16
_journal_year                    2018
_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     dual
_audit_creation_date             2018-01-28
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-06-28 deposited with the CCDC.
2018-10-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.5855(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.80656(8)
_cell_length_b                   17.94783(10)
_cell_length_c                   7.75427(6)
_cell_measurement_reflns_used    19058
_cell_measurement_temperature    150.04(10)
_cell_measurement_theta_max      73.2670
_cell_measurement_theta_min      4.3480
_cell_volume                     1407.943(19)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (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      150.04(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3046
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_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    -96.00  -2.00   1.00    1.00    --  -42.36 125.00  30.00   94
  2  \w   -115.00 -20.00   1.00    1.00    --  -42.36 -37.00  90.00   95
  3  \w   -115.00 -20.00   1.00    1.00    --  -42.36 -37.00 -90.00   95
  4  \w   -115.00 -20.00   1.00    1.00    --  -42.36 -37.00-180.00   95
  5  \w     23.00  97.00   1.00    1.00    --   42.36-125.00  90.00   74
  6  \w     23.00  97.00   1.00    1.00    --   42.36-125.00-180.00   74
  7  \w     94.00 178.00   1.00    1.00    --  106.00 125.00   0.00   84
  8  \w     31.00 130.00   1.00    1.00    --  106.00 -30.00  90.00   99
  9  \w     32.00 137.00   1.00    1.00    --  106.00 -77.00   0.00  105
 10  \w     34.00 121.00   1.00    1.00    --  106.00-125.00 120.00   87
 11  \w     94.00 178.00   1.00    1.00    --  106.00 125.00  90.00   84
 12  \w     34.00 121.00   1.00    1.00    --  106.00-125.00 -90.00   87
 13  \w     82.00 178.00   1.00    1.00    --  106.00  30.00 -30.00   96
 14  \w     25.00 109.00   1.00    1.00    --  106.00 -94.00 120.00   84
 15  \w     82.00 177.00   1.00    1.00    --  106.00  45.00  60.00   95
 16  \w     25.00 109.00   1.00    1.00    --  106.00 -94.00 -30.00   84
 17  \w     94.00 178.00   1.00    1.00    --  106.00 125.00 -30.00   84
 18  \w     34.00 121.00   1.00    1.00    --  106.00-125.00 -30.00   87
 19  \w     36.00 134.00   1.00    1.00    --  106.00 -61.00 -60.00   98
 20  \w     36.00 134.00   1.00    1.00    --  106.00 -61.00  90.00   98
 21  \w     82.00 178.00   1.00    1.00    --  106.00  30.00   0.00   96
 22  \w     34.00 121.00   1.00    1.00    --  106.00-125.00   0.00   87
 23  \w     94.00 178.00   1.00    1.00    --  106.00 125.00 120.00   84
 24  \w     35.00 130.00   1.00    1.00    --  106.00 -45.00-150.00   95
 25  \w   -116.00 -11.00   1.00    1.00    --  -42.36 -77.00-180.00  105
 26  \w   -116.00 -11.00   1.00    1.00    --  -42.36 -77.00  90.00  105
 27  \w   -113.00 -16.00   1.00    1.00    --  -42.36 -57.00  30.00   97
 28  \w   -116.00 -11.00   1.00    1.00    --  -42.36 -77.00 -90.00  105
 29  \w     11.00 116.00   1.00    1.00    --   42.36  77.00   0.00  105
 30  \w      1.00  82.00   1.00    1.00    --   42.36 -99.00 -90.00   81
 31  \w     82.00 178.00   1.00    1.00    --  106.00  30.00-120.00   96
 32  \w     78.00 176.00   1.00    1.00    --  106.00  61.00-180.00   98
 33  \w     78.00 176.00   1.00    1.00    --  106.00  61.00 -90.00   98
 34  \w     61.00 178.00   1.00    1.00    --  106.00  15.00-180.00  117
;
_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      -0.1277972000
_diffrn_orient_matrix_UB_12      -0.0458996000
_diffrn_orient_matrix_UB_13      -0.0429071000
_diffrn_orient_matrix_UB_21      -0.0826198000
_diffrn_orient_matrix_UB_22      0.0716983000
_diffrn_orient_matrix_UB_23      -0.0582116000
_diffrn_orient_matrix_UB_31      -0.0053316000
_diffrn_orient_matrix_UB_32      -0.0110458000
_diffrn_orient_matrix_UB_33      -0.1995004000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0957
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            27406
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.502
_diffrn_reflns_theta_min         4.370
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.808
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.27954
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (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    1.388
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2829
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0451
_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^)+(0.0727P)^2^+0.4940P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1204
_refine_ls_wR_factor_ref         0.1217
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2738
_reflns_number_total             2829
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob01768a2.cif
_cod_data_source_block           017rck17
_cod_depositor_comments
'Adding full bibliography for 7156565--7156567.cif.'
_cod_original_cell_volume        1407.942(18)
_cod_database_code               7156565
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         C18H14O4
_chemical_oxdiff_usercomment
'017RCK17 colourless block 0.4 0.4 0.12 EtOAc/hexane Cu150K 4x4'
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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:
 C14(H14A,H14B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C10(H10), C2(H2), C5(H5), C4(H4), C3(H3), C19(H19)
2.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_shelx_res_checksum              4609
_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 4.768
_oxdiff_exptl_absorpt_empirical_full_min 0.484