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_7156566
_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         'C26 H19 B F2 N2 O3'
_chemical_formula_sum            'C26 H19 B F2 N2 O3'
_chemical_formula_weight         456.24
_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             2018-03-13
_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                 104.5629(17)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.4282(2)
_cell_length_b                   25.2193(4)
_cell_length_c                   7.59768(13)
_cell_measurement_reflns_used    8515
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      78.0940
_cell_measurement_theta_min      4.3620
_cell_volume                     2119.39(6)
_computing_cell_refinement       'CrysAlisPro 1.171.39.44a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.44a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.44a (Rigaku OD, 2018)'
_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      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1417
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.984
_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 -18.00   1.00    8.22    --  -42.09 -38.00  90.00   98
  2  \w    -67.00  32.00   1.00    8.22    --  -42.09  38.00  90.00   99
  3  \w     18.00  98.00   1.00    8.22    --   42.09-125.00-180.00   80
  4  \w     86.00 178.00   1.00   32.90    --  114.00  30.00   0.00   92
  5  \w     38.00 116.00   1.00   32.90    --  114.00-111.00 120.00   78
  6  \w     32.00 109.00   1.00   32.90    --  114.00 -95.00 150.00   77
  7  \w     88.00 178.00   1.00   32.90    --  114.00  45.00-120.00   90
  8  \w     86.00 178.00   1.00   32.90    --  114.00  30.00 -90.00   92
  9  \w     32.00 109.00   1.00   32.90    --  114.00 -95.00-180.00   77
 10  \w    100.00 178.00   1.00   32.90    --  114.00 111.00-120.00   78
 11  \w     41.00 140.00   1.00   32.90    --  114.00 -45.00 -60.00   99
 12  \w   -118.00 -56.00   1.00    8.22    --  -42.09 -77.00 -30.00   62
;
_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      0.0824372000
_diffrn_orient_matrix_UB_12      -0.0008890000
_diffrn_orient_matrix_UB_13      -0.1323021000
_diffrn_orient_matrix_UB_21      -0.1101447000
_diffrn_orient_matrix_UB_22      0.0110579000
_diffrn_orient_matrix_UB_23      -0.1602445000
_diffrn_orient_matrix_UB_31      0.0214593000
_diffrn_orient_matrix_UB_32      0.0600457000
_diffrn_orient_matrix_UB_33      0.0276162000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            13289
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.493
_diffrn_reflns_theta_min         3.505
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.877
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80232
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.44a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_description       block
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         4488
_refine_ls_number_restraints     141
_refine_ls_restrained_S_all      1.125
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0424
_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^)+(0.0585P)^2^+0.6242P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1123
_refine_ls_wR_factor_ref         0.1148
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4198
_reflns_number_total             4488
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob01768a2.cif
_cod_data_source_block           026rck18
_cod_depositor_comments
'Adding full bibliography for 7156565--7156567.cif.'
_cod_database_code               7156566
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         C26H19BF2N2O3
_chemical_oxdiff_usercomment
'026RCK18 red block 0.25 0.10 0.07 chcl3 Cu150K 4x4'
_shelx_estimated_absorpt_t_max   0.917
_shelx_estimated_absorpt_t_min   0.811
_reflns_odcompleteness_completeness 99.77
_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. Restrained distances
 N26-N30 \\sim N26-F28 \\sim N26-F29 \\sim N30-F28 \\sim N30-F29 \\sim F28-F29
 with sigma of 0.04
 B27-N26 \\sim B27-N30 \\sim B27-F28 \\sim B27-F29
 with sigma of 0.02
 N26-N30 \\sim F129-F128
 with sigma of 0.04
 B127-N26 \\sim B127-N30 \\sim B127-F129 \\sim B127-F128
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
B27 \\sim F29 \\sim F28: within 2A with sigma of 0.04 and sigma for terminal
atoms of 0.08
F129 \\sim F128 \\sim B127 \\sim N30 \\sim N26: within 2A with sigma of 0.04
and sigma for terminal atoms of 0.08
F28 \\sim B27 \\sim F128 \\sim B127 \\sim F29 \\sim F129: within 2A with sigma
of 0.04 and sigma for terminal atoms of 0.08
B127 \\sim N26 \\sim N30: within 2A with sigma of 0.04 and sigma for terminal
atoms of 0.08
B127 \\sim N30 \\sim N26 \\sim C22 \\sim C34 \\sim B27: within 2A with sigma of
0.04 and sigma for terminal atoms of 0.08
4. Others
 Sof(F129)=Sof(B127)=Sof(F128)=1-FVAR(1)
 Sof(F28)=Sof(F29)=Sof(B27)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C17(H17A,H17B)
5.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C10(H10), C5(H5), C4(H4), C23(H23), C2(H2), C33(H33), C3(H3),
 C25(H25), C32(H32), C24(H24), C31(H31)
5.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_shelx_res_checksum              79320
_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 1.294
_oxdiff_exptl_absorpt_empirical_full_min 0.830