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

data_1572465
_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         'C30 H28 O4'
_chemical_formula_sum            'C30 H28 O4'
_chemical_formula_weight         452.52
_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     direct
_audit_creation_date             2022-04-08
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2023-09-18 deposited with the CCDC.	2024-07-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.323(8)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   23.5231(19)
_cell_length_b                   8.2852(7)
_cell_length_c                   24.9724(19)
_cell_measurement_reflns_used    3129
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      63.8820
_cell_measurement_theta_min      2.3030
_cell_volume                     4693.9(7)
_computing_cell_refinement       'CrysAlisPro 1.171.42.50a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.50a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.50a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.945
_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    -45.00   2.00   1.00    5.00    --   43.53  40.00-120.00   47
  2  \w     33.00 133.00   1.00    5.00    --   43.53  50.00 150.00  100
  3  \w    -29.00  -3.00   1.00    5.00    --   43.53  50.00 150.00   26
  4  \w    -43.00   5.00   1.00    5.00    --   46.07  60.00-120.00   48
  5  \w    -11.00 103.00   1.00    5.00    --   46.07  60.00 -90.00  114
  6  \w    -41.00 -16.00   1.00    5.00    --   46.07  20.00 -90.00   25
  7  \w     55.00  82.00   1.00    5.00    --   46.07  60.00-120.00   27
  8  \w    -43.00 135.00   1.00    5.00    --   46.07  60.00 -60.00  178
  9  \w    173.00 198.00   1.00   10.00    --  108.20  52.00 -34.56   25
 10  \w     19.00  45.00   1.00   10.00    --  108.20  53.00 -19.80   26
 11  \w     19.00  45.00   1.00   10.00    --  108.20  52.00 -34.56   26
 12  \w     19.00  45.00   1.00   10.00    --  108.20  57.00 -84.71   26
 13  \w     19.00  46.00   1.00   10.00    --  108.20  56.00 -82.05   27
 14  \w     20.00 132.00   1.00   10.00    --  108.20  40.00 -90.00  112
 15  \w     19.00  46.00   1.00   10.00    --  108.20  55.00 -16.37   27
 16  \w     93.00 119.00   1.00   10.00    --  108.20  59.00-113.47   26
 17  \w     19.00  45.00   1.00   10.00    --  108.20  50.00-150.00   26
 18  \w     19.00  45.00   1.00   10.00    --  108.20  59.00-113.47   26
 19  \w     19.00  44.00   1.00   10.00    --  108.20  52.00 -46.59   25
 20  \w     86.00 124.00   1.00   10.00    --  108.20  50.00-150.00   38
 21  \w     19.00  46.00   1.00   10.00    --  108.20  50.00   0.00   27
 22  \w     19.00  51.00   1.00   10.00    --  108.20  40.00   0.00   32
 23  \w     83.00 113.00   1.00   10.00    --  108.20  40.00   0.00   30
 24  \w     19.00  45.00   1.00   10.00    --  108.20  50.00 -60.00   26
 25  \w     19.00  45.00   1.00   10.00    --  108.20  50.00-120.00   26
 26  \w     19.00  44.00   1.00   10.00    --  108.20  50.00 -90.00   25
 27  \w     19.00 197.00   1.00   10.00    --  108.20  53.00-140.56  178
 28  \w     19.00 138.00   1.00   10.00    --  108.20  40.00-120.00  119
 29  \w     19.00 197.00   1.00   10.00    --  108.20  40.00 -30.00  178
 30  \w     19.00 116.00   1.00   10.00    --  108.20  40.00 -60.00   97
;
_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      0.0190998000
_diffrn_orient_matrix_UB_12      -0.0036604000
_diffrn_orient_matrix_UB_13      -0.0544335000
_diffrn_orient_matrix_UB_21      0.0630824000
_diffrn_orient_matrix_UB_22      0.0476433000
_diffrn_orient_matrix_UB_23      0.0321625000
_diffrn_orient_matrix_UB_31      0.0163592000
_diffrn_orient_matrix_UB_32      -0.1796636000
_diffrn_orient_matrix_UB_33      0.0096979000
_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  0.1176
_diffrn_reflns_av_unetI/netI     0.0837
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            49445
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.192
_diffrn_reflns_theta_min         2.296
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_exptl_absorpt_coefficient_mu    0.670
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76638
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.50a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_description       plank
_exptl_crystal_F_000             1920
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.386
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       0.00124(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     618
_refine_ls_number_reflns         9419
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.1398
_refine_ls_R_factor_gt           0.0713
_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^)+(0.0824P)^2^+2.9890P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1605
_refine_ls_wR_factor_ref         0.2012
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5128
_reflns_number_total             9419
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc03968h2.cif
_cod_data_source_block           s6053l
_cod_original_cell_volume        4694.0(7)
_cod_database_code               1572465
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.987
_shelx_estimated_absorpt_t_min   0.918
_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:
 C15(H15), C37(H37), C38(H38), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C60(H60A,H60B), C6(H6A,H6B), C46(H46A,H46B), C7(H7A,H7B), C26(H26A,H26B),
 C45(H45A,H45B), C18(H18A,H18B), C52(H52A,H52B)
2.c Aromatic/amide H refined with riding coordinates:
 C50(H50), C24(H24), C4(H4), C20(H20), C3(H3), C41(H41), C9(H9), C10(H10),
 C28(H28), C57(H57), C55(H55), C49(H49), C48(H48), C43(H43), C2(H2), C22(H22),
 C58(H58), C32(H32), C64(H64), C54(H54), C11(H11), C62(H62), C31(H31), C42(H42),
  C56(H56), C65(H65), C66(H66), C30(H30), C63(H63), C23(H23), C29(H29), C21(H21)
2.d Idealised tetrahedral OH refined as rotating group:
 O33(H33), O67(H67), O68(H68), O34(H34)
;
_shelx_res_checksum              12623
_shelx_hkl_checksum              9047
_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 1.692
_oxdiff_exptl_absorpt_empirical_full_min 0.696