Mechanochemical generation of aryne.
Cheng, Qianqian; De Bo, Guillaume; Chemical science 15 (2024) 13181–13184; doi:10.1039/d4sc03968h

data_1572464
_publ_section_title
;
 Mechanochemical generation of aryne.
;
_journal_issue                   33
_journal_name_full               'Chemical science'
_journal_page_first              13181
_journal_page_last               13184
_journal_paper_doi               10.1039/d4sc03968h
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C15 H14 O2'
_chemical_formula_sum            'C15 H14 O2'
_chemical_formula_weight         226.26
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-03-27
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-09-18 deposited with the CCDC.	2024-07-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.218(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.0807(4)
_cell_length_b                   4.92885(12)
_cell_length_c                   23.4456(5)
_cell_measurement_reflns_used    11742
_cell_measurement_temperature    99.97(13)
_cell_measurement_theta_max      75.8890
_cell_measurement_theta_min      2.5390
_cell_volume                     2380.90(9)
_computing_cell_refinement       'CrysAlisPro 1.171.42.80a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.80a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.80a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.97(13)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.981
_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     43.00  87.00   1.00    1.00    --   46.08  12.00 -97.00   44
  2  \w    147.00 197.00   1.00    3.00    --  108.20  12.00 -97.00   50
  3  \w     47.00 118.00   1.00    3.00    --  108.20  12.00 -97.00   71
  4  \w    -40.00 -15.00   1.00    1.00    --   43.52  40.00   0.00   25
  5  \w     19.00  44.00   1.00    1.00    --   43.52  12.00 -97.00   25
  6  \w     52.00  77.00   1.00    1.00    --   43.52  40.00   0.00   25
  7  \w    -42.00  81.00   1.00    1.00    --   46.08  20.00   0.00  123
  8  \w    -41.00 -15.00   1.00    1.00    --   46.08  60.00   0.00   26
  9  \w    -42.00  29.00   1.00    1.00    --   46.08  30.00  90.00   71
 10  \w     88.00 134.00   1.00    1.00    --   46.08  20.00   0.00   46
 11  \w    -41.00   0.00   1.00    1.00    --   46.08  40.00  30.00   41
 12  \w    109.00 135.00   1.00    1.00    --   46.08  40.00  30.00   26
 13  \w    -39.00 135.00   1.00    1.00    --   46.08  60.00  60.00  174
 14  \w    110.00 135.00   1.00    1.00    --   46.08  12.00 -97.00   25
 15  \w     94.00 120.00   1.00    3.00    --  108.20  57.00  72.41   26
 16  \w    125.00 165.00   1.00    3.00    --  108.20  58.00 -50.02   40
 17  \w    168.00 193.00   1.00    3.00    --  108.20  57.00  72.41   25
 18  \w     65.00  93.00   1.00    3.00    --  108.20  57.00  72.41   28
 19  \w     20.00  51.00   1.00    3.00    --  108.20  57.00  72.41   31
 20  \w     19.00  45.00   1.00    3.00    --  108.20  58.00 -50.02   26
 21  \w     19.00  45.00   1.00    3.00    --  108.20  59.00  -1.36   26
 22  \w     21.00  48.00   1.00    3.00    --  108.20  60.00  41.39   27
 23  \w    118.00 144.00   1.00    3.00    --  108.20  60.00  25.14   26
 24  \w     19.00  78.00   1.00    3.00    --  108.20  56.00 -16.94   59
 25  \w    109.00 198.00   1.00    3.00    --  108.20  60.00  41.39   89
 26  \w     20.00  55.00   1.00    3.00    --  108.20  50.00  30.00   35
 27  \w     20.00  46.00   1.00    3.00    --  108.20  55.00  33.91   26
 28  \w     19.00 198.00   1.00    3.00    --  108.20  30.00-150.00  179
 29  \w     19.00  45.00   1.00    3.00    --  108.20  56.00  60.95   26
 30  \w     20.00 187.00   1.00    3.00    --  108.20  30.00 -60.00  167
 31  \w     67.00  93.00   1.00    3.00    --  108.20  50.00  10.14   26
 32  \w     19.00  68.00   1.00    3.00    --  108.20  59.00 -43.02   49
 33  \w     19.00  60.00   1.00    3.00    --  108.20  50.00   0.00   41
 34  \w    158.00 184.00   1.00    3.00    --  108.20  46.00  48.77   26
 35  \w     69.00  94.00   1.00    3.00    --  108.20  50.00 -60.00   25
 36  \w     68.00  94.00   1.00    3.00    --  108.20  60.00  25.14   26
 37  \w    113.00 139.00   1.00    3.00    --  108.20  60.00 -26.90   26
 38  \w     19.00  44.00   1.00    3.00    --  108.20  50.00 -60.00   25
 39  \w     19.00  44.00   1.00    3.00    --  108.20  60.00 -26.90   25
 40  \w     19.00  45.00   1.00    3.00    --  108.20  40.00 -60.00   26
 41  \w     19.00  66.00   1.00    3.00    --  108.20  46.00  48.77   47
 42  \w    143.00 168.00   1.00    3.00    --  108.20  60.00 -34.22   25
 43  \w     83.00 198.00   1.00    3.00    --  108.20  40.00  30.00  115
 44  \w     20.00  63.00   1.00    3.00    --  108.20  45.00 -47.17   43
 45  \w     20.00  75.00   1.00    3.00    --  108.20  41.00 -76.77   55
 46  \w    130.00 156.00   1.00    3.00    --  108.20  41.00 -76.77   26
 47  \w     20.00  45.00   1.00    3.00    --  108.20  60.00  25.14   25
 48  \w     19.00  45.00   1.00    3.00    --  108.20  54.00  12.71   26
 49  \w     21.00  53.00   1.00    3.00    --  108.20  50.00 -30.00   32
 50  \w     19.00  45.00   1.00    3.00    --  108.20  58.00  66.28   26
 51  \w     19.00  46.00   1.00    3.00    --  108.20  50.00  90.00   27
 52  \w    107.00 132.00   1.00    3.00    --  108.20  60.00 -34.22   25
 53  \w    171.00 196.00   1.00    3.00    --  108.20  59.00  50.48   25
 54  \w     19.00  45.00   1.00    3.00    --  108.20  59.00  50.48   26
 55  \w     30.00  55.00   1.00    3.00    --  108.20  49.00  55.18   25
 56  \w     19.00  89.00   1.00    3.00    --  108.20  52.00  60.56   70
 57  \w     19.00  70.00   1.00    3.00    --  108.20  51.00  20.37   51
 58  \w     19.00  45.00   1.00    3.00    --  108.20  55.00  45.11   26
 59  \w     19.00  45.00   1.00    3.00    --  108.20  50.00  10.14   26
 60  \w     19.00  45.00   1.00    3.00    --  108.20  60.00 -34.22   26
 61  \w     19.00  45.00   1.00    3.00    --  108.20  49.00  29.00   26
 62  \w     19.00  46.00   1.00    3.00    --  108.20  59.00   2.30   27
 63  \w    139.00 164.00   1.00    3.00    --  108.20  59.00  -1.36   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): quarter-chi single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0544989000
_diffrn_orient_matrix_UB_12      0.0660326000
_diffrn_orient_matrix_UB_13      0.0324131000
_diffrn_orient_matrix_UB_21      0.0495998000
_diffrn_orient_matrix_UB_22      -0.0064661000
_diffrn_orient_matrix_UB_23      0.0586386000
_diffrn_orient_matrix_UB_31      0.0127977000
_diffrn_orient_matrix_UB_32      0.3053238000
_diffrn_orient_matrix_UB_33      -0.0057619000
_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  0.0793
_diffrn_reflns_av_unetI/netI     0.0553
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            38693
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.186
_diffrn_reflns_theta_min         2.563
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_exptl_absorpt_coefficient_mu    0.660
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77197
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.80a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_description       plate
_exptl_crystal_F_000             960
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.342
_exptl_crystal_size_mid          0.118
_exptl_crystal_size_min          0.025
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         4891
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0653
_refine_ls_R_factor_gt           0.0578
_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^)+(0.0761P)^2^+1.4906P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1532
_refine_ls_wR_factor_ref         0.1604
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4198
_reflns_number_total             4891
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc03968h2.cif
_cod_data_source_block           s6277l
_cod_original_cell_volume        2380.91(9)
_cod_database_code               1572464
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.806
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C29(H29), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C7(H7A,H7B), C28(H28A,H28B), C22(H22A,H22B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C24(H24), C11(H11), C25(H25), C10(H10), C26(H26), C3(H3), C1(H1),
 C4(H4), C5(H5), C2(H2A), C16(H16), C20(H20), C17(H17), C18(H18), C19(H19)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2), O4(H4A)
;
_shelx_res_checksum              57062
_shelx_hkl_checksum              80628
_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 2.853
_oxdiff_exptl_absorpt_empirical_full_min 0.610