A rational design strategy of radical-type mechanophores with thermal tolerance.
Lu, Yi; Sugita, Hajime; Mikami, Koichiro; Aoki, Daisuke; Otsuka, Hideyuki; Chemical science 14 (2023) 8792–8797; doi:10.1039/d3sc02991c

data_1569616
_publ_section_title
;
 A rational design strategy of radical-type mechanophores with thermal
 tolerance.
;
_journal_issue                   33
_journal_name_full               'Chemical science'
_journal_page_first              8792
_journal_page_last               8797
_journal_paper_doi               10.1039/d3sc02991c
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C19 H26 N O2'
_chemical_formula_sum            'C19 H26 N O2'
_chemical_formula_weight         300.41
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-06-24
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2022-09-15 deposited with the CCDC.	2023-07-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.5240(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.46250(10)
_cell_length_b                   15.60580(10)
_cell_length_c                   17.06840(10)
_cell_measurement_reflns_used    17469
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      75.2190
_cell_measurement_theta_min      4.3480
_cell_volume                     3558.46(5)
_computing_cell_refinement       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.15
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.983
_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    103.00 138.00   0.50    0.17    --  108.48  77.00 150.00   70
  2  \w     86.00 178.00   0.50    0.17    --  108.48  45.00 -90.00  184
  3  \w     85.00 178.00   0.50    0.17    --  108.48  30.00-120.00  186
  4  \w    -42.00  34.00   0.50    0.05    --  -43.71  37.00-150.00  152
  5  \w    -28.00  37.00   0.50    0.05    --  -43.71  19.00   0.00  130
  6  \w    -42.00  34.00   0.50    0.05    --  -43.71  37.00  60.00  152
  7  \w    -28.00  37.00   0.50    0.05    --  -43.71  19.00 120.00  130
  8  \w    -19.00  76.00   0.50    0.05    --   43.71 -85.00 -11.00  190
  9  \w     36.00  97.00   0.50    0.05    --   43.71-125.00-150.00  122
 10  \w     36.00 105.00   0.50    0.17    --  108.48-125.00   0.00  138
 11  \w     35.00 101.00   0.50    0.17    --  108.48 -94.00 -90.00  132
 12  \w     81.00 108.00   0.50    0.17    --  108.48-125.00  90.00   54
 13  \w     44.00  75.00   0.50    0.17    --  108.48-125.00  90.00   62
 14  \w     36.00 108.00   0.50    0.17    --  108.48-125.00 120.00  144
 15  \w     35.00 103.00   0.50    0.17    --  108.48 -94.00 120.00  136
 16  \w     34.00 141.00   0.50    0.17    --  108.48 -85.00 -11.00  214
 17  \w     43.00 103.00   0.50    0.17    --  108.48 -77.00-180.00  120
 18  \w     37.00  70.00   0.50    0.17    --  108.48 -61.00-180.00   66
 19  \w     34.00  72.00   0.50    0.17    --  108.48 -61.00 -90.00   76
 20  \w     34.00  72.00   0.50    0.17    --  108.48 -61.00  30.00   76
 21  \w     34.00  72.00   0.50    0.17    --  108.48 -61.00 120.00   76
 22  \w    -36.00  29.00   0.50    0.05    --   43.71 -19.00-120.00  130
 23  \w     98.00 133.00   0.50    0.17    --  108.48 125.00 -60.00   70
 24  \w    143.00 169.00   0.50    0.17    --  108.48 125.00 -60.00   52
 25  \w    118.00 144.00   0.50    0.17    --  108.48  85.00 106.00   52
 26  \w    150.00 178.00   0.50    0.17    --  108.48  85.00 106.00   56
 27  \w   -128.00 -22.00   0.50    0.17    --  -96.00  85.00 106.00  212
 28  \w    -76.00  31.00   0.50    0.05    --  -43.71  85.00 106.00  214
 29  \w    -82.00 -15.00   0.50    0.05    --  -43.71 125.00-120.00  134
 30  \w    -83.00 -22.00   0.50    0.17    --  -96.00 125.00 -30.00  122
 31  \w    -50.00 -20.00   0.50    0.17    --  -96.00  45.00  60.00   60
 32  \w    -50.00 -20.00   0.50    0.17    --  -96.00  45.00  30.00   60
 33  \w    -50.00 -20.00   0.50    0.17    --  -96.00  45.00-150.00   60
 34  \w    -50.00 -20.00   0.50    0.17    --  -96.00  45.00-180.00   60
 35  \w   -175.00 -72.00   0.50    0.17    --  -96.00 -30.00-120.00  206
 36  \w   -172.00 -74.00   0.50    0.17    --  -96.00 -45.00 -60.00  196
 37  \w   -170.00 -81.00   0.50    0.17    --  -96.00 -85.00 -11.00  178
 38  \w   -170.00 -85.00   0.50    0.17    --  -96.00 -94.00  60.00  170
 39  \w   -170.00 -81.00   0.50    0.17    --  -96.00 -77.00  60.00  178
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0501938000
_diffrn_orient_matrix_UB_12      -0.0594255000
_diffrn_orient_matrix_UB_13      0.0440990000
_diffrn_orient_matrix_UB_21      0.0864143000
_diffrn_orient_matrix_UB_22      -0.0646363000
_diffrn_orient_matrix_UB_23      0.0188578000
_diffrn_orient_matrix_UB_31      0.0574650000
_diffrn_orient_matrix_UB_32      0.0451571000
_diffrn_orient_matrix_UB_33      0.0851180000
_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  0.0446
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            26464
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.350
_diffrn_reflns_theta_min         4.357
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.563
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79047
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.110a (Rigaku Oxford Diffraction, 2021)
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    1.121
_exptl_crystal_description       block
_exptl_crystal_F_000             1304
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: heptane/ethyl acetate'
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         3624
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0374
_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^)+(0.0449P)^2^+2.6683P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0948
_refine_ls_wR_factor_ref         0.0958
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3443
_reflns_number_total             3624
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc02991c2.cif
_cod_data_source_block           Sugita_B2
_cod_depositor_comments          'Adding full bibliography for 1569616.cif.'
_cod_database_code               1569616
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O'
_shelx_estimated_absorpt_t_max   0.925
_shelx_estimated_absorpt_t_min   0.819
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C7(H7), C9(H9)
2.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C15(H15A,H15B,H15C), C14(H14A,H14B,H14C), C17(H17A,H17B,
 H17C), C13(H13A,H13B,H13C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C)
;
_shelx_res_checksum              75571
_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 1.192
_oxdiff_exptl_absorpt_empirical_full_min 0.719