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_7156567
_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 O3'
_chemical_formula_sum            'C18 H14 O3'
_chemical_formula_weight         278.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-I 2ya'
_symmetry_space_group_name_H-M   'I 1 2/a 1'
_atom_sites_solution_primary     dual
_audit_creation_date             2018-01-16
_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                 105.284(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.8350(8)
_cell_length_b                   7.1072(3)
_cell_length_c                   21.7952(9)
_cell_measurement_reflns_used    6733
_cell_measurement_temperature    150.03(10)
_cell_measurement_theta_max      73.1460
_cell_measurement_theta_min      4.1240
_cell_volume                     2814.4(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.03(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3046
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.9947
_diffrn_measured_fraction_theta_max 0.9947
_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   -115.00 -20.00   1.00    2.79    --  -42.36 -37.00  30.00   95
  2  \w     23.00  97.00   1.00    2.79    --   42.36-125.00-120.00   74
  3  \w     23.00  97.00   1.00    2.79    --   42.36-125.00-180.00   74
  4  \w      1.00  82.00   1.00    2.79    --   42.36 -99.00   0.00   81
  5  \w     31.00 130.00   1.00   11.16    --  106.00 -30.00-120.00   99
  6  \w     31.00 130.00   1.00   11.16    --  106.00 -30.00  60.00   99
  7  \w     35.00 130.00   1.00   11.16    --  106.00 -45.00-120.00   95
  8  \w     94.00 178.00   1.00   11.16    --  106.00 125.00 -30.00   84
  9  \w     35.00 130.00   1.00   11.16    --  106.00 -45.00  90.00   95
 10  \w     36.00 134.00   1.00   11.16    --  106.00 -61.00-150.00   98
 11  \w     25.00 109.00   1.00   11.16    --  106.00 -94.00-120.00   84
 12  \w     94.00 178.00   1.00   11.16    --  106.00 125.00-180.00   84
 13  \w     19.00 178.00   1.00   11.16    --  106.00   0.00   0.00  159
 14  \w   -113.00 -16.00   1.00    2.79    --  -42.36 -57.00 150.00   97
 15  \w   -113.00 -16.00   1.00    2.79    --  -42.36 -57.00 -30.00   97
 16  \w   -116.00 -11.00   1.00    2.79    --  -42.36 -77.00  90.00  105
 17  \w   -116.00 -11.00   1.00    2.79    --  -42.36 -77.00 -90.00  105
 18  \w     61.00 178.00   1.00   11.16    --  106.00  15.00 120.00  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      -0.0681883000
_diffrn_orient_matrix_UB_12      -0.0626289000
_diffrn_orient_matrix_UB_13      -0.0522253000
_diffrn_orient_matrix_UB_21      -0.0450658000
_diffrn_orient_matrix_UB_22      0.1611378000
_diffrn_orient_matrix_UB_23      0.0186946000
_diffrn_orient_matrix_UB_31      0.0226424000
_diffrn_orient_matrix_UB_32      0.1308167000
_diffrn_orient_matrix_UB_33      -0.0478289000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0633
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            14083
_diffrn_reflns_theta_full        73.3840
_diffrn_reflns_theta_max         73.38
_diffrn_reflns_theta_min         4.21
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.722
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.24910
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (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    1.3135
_exptl_crystal_description       block
_exptl_crystal_F_000             1171.8899
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.3559
_refine_diff_density_min         -0.2452
_refine_diff_density_rms         0.0649
_refine_ls_d_res_high            0.8045
_refine_ls_d_res_low             10.5094
_refine_ls_goodness_of_fit_ref   1.0443
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    24
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2812
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0443
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0508
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0900P)^2^+1.1282P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1342
_refine_ls_wR_factor_ref         0.1432
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              23
_reflns_limit_h_min              0
_reflns_limit_k_max              8
_reflns_limit_k_min              0
_reflns_limit_l_max              25
_reflns_limit_l_min              -26
_reflns_number_gt                2478
_reflns_number_total             2812
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c8ob01768a2.cif
_cod_data_source_block           021RCK17
_cod_depositor_comments
'Adding full bibliography for 7156565--7156567.cif.'
_cod_database_code               7156567
_chemical_oxdiff_usercomment
'021RCK17 coliurless block 0.2 0.15 0.12 chcl3/hex Cu150K 4x4'
_reflns_odcompleteness_completeness 99.93
_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:
 C9(H9), C10(H10), C12(H12), C5(H5), C4(H4), C3(H3), C2(H2)
2.c Idealised Me refined as rotating group:
 C21(H21a,H21b,H21c)
;
_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 4.837
_oxdiff_exptl_absorpt_empirical_full_min 0.423