Mechanochemical reactivity inhibited, prohibited and reversed by liquid additives: examples from crystal-form screens
Arhangelskis, Mihails; Bučar, Dejan-Krešimir; Bordignon, Simone; Chierotti, Michele R.; Stratford, Samuel A.; Voinovich, Dario; Jones, William; Hasa, Dritan; Chemical Science 12 (2021) 3264–3269; doi:10.1039/D0SC05071G

data_1560123
_publ_section_title
;
 Mechanochemical reactivity inhibited, prohibited and reversed by liquid
 additives: examples from crystal-form screens
;
_journal_issue                   9
_journal_name_full               'Chemical Science'
_journal_page_first              3264
_journal_page_last               3269
_journal_paper_doi               10.1039/D0SC05071G
_journal_volume                  12
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H27 N2 O2, C2 H O4'
_chemical_formula_sum            'C24 H28 N2 O6'
_chemical_formula_weight         440.48
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2020-04-19
_audit_creation_method
;
Olex2 1.3
(compiled 2020.01.31 svn.r88ba2a32 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2020-08-20 deposited with the CCDC.	2020-12-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.3560(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.9007(2)
_cell_length_b                   6.30220(10)
_cell_length_c                   20.9554(2)
_cell_measurement_reflns_used    30841
_cell_measurement_temperature    150.0(1)
_cell_measurement_theta_max      72.4140
_cell_measurement_theta_min      4.3300
_cell_volume                     2279.66(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2031
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_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      1.00  30.00   1.00    1.03    --   38.00  89.00 -23.73   29
  2  \w      9.00  42.00   1.00    1.03    --   42.00  78.00-122.82   33
  3  \w   -123.00  -2.00   1.00    1.03    --  -42.62 -19.00  90.00  121
  4  \w   -117.00 -18.00   1.00    1.03    --  -42.62 -38.00   0.00   99
  5  \w    -87.00  -6.00   1.00    1.03    --  -42.62 125.00 150.00   81
  6  \w   -117.00 -18.00   1.00    1.03    --  -42.62 -38.00 150.00   99
  7  \w     27.00  99.00   1.00    1.03    --   42.62-125.00   0.00   72
  8  \w     13.00  42.00   1.00    1.03    --   46.00  78.00 150.72   29
  9  \w     13.00  42.00   1.00    1.03    --   46.00  78.00-117.21   29
 10  \w     13.00  42.00   1.00    1.03    --   46.00  78.00  75.07   29
 11  \w     26.00 133.00   1.00    1.03    --   58.00  74.00 -72.92  107
 12  \w     30.00 137.00   1.00    1.03    --   62.00  74.00-123.64  107
 13  \w     30.00 137.00   1.00    1.03    --   62.00  74.00  11.24  107
 14  \w     35.00 140.00   1.00    1.03    --   66.00  71.00-151.15  105
 15  \w     34.00 141.00   1.00    1.03    --   66.00  73.00 -49.90  107
 16  \w     34.00 141.00   1.00    1.03    --   66.00  74.00  82.25  107
 17  \w     40.00 143.00   1.00    1.03    --   70.00  64.00 171.26  103
 18  \w     39.00 144.00   1.00    1.03    --   70.00  71.00 -28.50  105
 19  \w     46.00 146.00   1.00    4.15    --   74.00  56.00  93.78  100
 20  \w     43.00 148.00   1.00    4.15    --   74.00  70.00 116.46  105
 21  \w     45.00 147.00   1.00    4.15    --   74.00  63.00 -88.06  102
 22  \w     47.00 152.00   1.00    4.15    --   78.00  71.00  32.07  105
 23  \w     63.00 162.00   1.00    4.15    --   90.00  50.00 -18.72   99
 24  \w     63.00 168.00   1.00    4.15    --   94.00  71.00-154.43  105
 25  \w     65.00 167.00   1.00    4.15    --   94.00  63.00 -80.82  102
 26  \w     97.00 178.00   1.00    4.15    --  104.49 125.00 -60.00   81
 27  \w     75.00 177.00   1.00    4.15    --  104.49  61.00  60.00  102
 28  \w     75.00 177.00   1.00    4.15    --  104.49  61.00-120.00  102
 29  \w     22.00 106.00   1.00    4.15    --  104.49 -94.00 -30.00   84
 30  \w     75.00 177.00   1.00    4.15    --  104.49  61.00-180.00  102
 31  \w     75.00 177.00   1.00    4.15    --  104.49  61.00 120.00  102
 32  \w     31.00 113.00   1.00    4.15    --  104.49-125.00 -60.00   82
 33  \w     22.00 106.00   1.00    4.15    --  104.49 -94.00 120.00   84
 34  \w     75.00 177.00   1.00    4.15    --  104.49  61.00   0.00  102
 35  \w     75.00 177.00   1.00    4.15    --  104.49  61.00 -30.00  102
 36  \w     22.00 106.00   1.00    4.15    --  104.49 -94.00-120.00   84
 37  \w     22.00 106.00   1.00    4.15    --  104.49 -94.00  30.00   84
 38  \w     75.00 177.00   1.00    4.15    --  104.49  61.00  30.00  102
 39  \w     75.00 177.00   1.00    4.15    --  104.49  61.00  90.00  102
 40  \w     97.00 178.00   1.00    4.15    --  104.49 125.00-180.00   81
 41  \w     73.00 178.00   1.00    4.15    --  104.49  72.00 -82.41  105
 42  \w     75.00 177.00   1.00    4.15    --  104.49  61.00 150.00  102
 43  \w     -4.00  22.00   1.00    1.03    --   34.00  93.00 129.18   26
 44  \w     -4.00  23.00   1.00    1.03    --   34.00  92.00   8.00   27
 45  \w     27.00  99.00   1.00    1.03    --   42.62-125.00-180.00   72
 46  \w    -46.00 131.00   1.00    1.03    --   42.62   0.00-180.00  177
 47  \w     10.00  42.00   1.00    1.03    --   42.62  79.00 -89.23   32
 48  \w     22.00 129.00   1.00    1.03    --   54.00  74.00  -7.94  107
 49  \w     22.00 129.00   1.00    1.03    --   54.00  74.00 124.92  107
 50  \w     27.00 132.00   1.00    1.03    --   58.00  72.00 141.74  105
 51  \w     31.00 136.00   1.00    1.03    --   62.00  72.00  47.03  105
 52  \w     34.00 141.00   1.00    1.03    --   66.00  74.00  60.23  107
 53  \w     35.00 139.00   1.00    1.03    --   66.00  69.00 151.62  104
 54  \w     34.00 141.00   1.00    1.03    --   66.00  74.00 121.82  107
 55  \w     42.00 143.00   1.00    1.03    --   70.00  57.00   9.67  101
 56  \w     45.00 146.00   1.00    4.15    --   74.00  62.00-117.34  101
 57  \w     53.00 154.00   1.00    4.15    --   82.00  60.00-103.58  101
 58  \w     79.00 178.00   1.00    4.15    --  104.49  45.00-180.00   99
 59  \w     79.00 143.00   1.00    4.15    --  104.49  45.00 -30.00   64
 60  \w    103.00 178.00   1.00    4.15    --  104.49  77.00  60.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0513388000
_diffrn_orient_matrix_UB_12      -0.0173803000
_diffrn_orient_matrix_UB_13      -0.0483087000
_diffrn_orient_matrix_UB_21      0.0567210000
_diffrn_orient_matrix_UB_22      0.1627697000
_diffrn_orient_matrix_UB_23      0.0415402000
_diffrn_orient_matrix_UB_31      0.0459393000
_diffrn_orient_matrix_UB_32      -0.1815160000
_diffrn_orient_matrix_UB_33      0.0418887000
_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  0.0379
_diffrn_reflns_av_unetI/netI     0.0147
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            40113
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.563
_diffrn_reflns_theta_min         4.376
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.763
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66318
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_description       prism
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
;
 Flack x determined using 1785 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, S.; Flack, H. D.; Wagner, T. (2013). Acta Cryst. B69, 249-259).
 Hooft y determined according to Hooft et al. 
 (Hooft, R. W. W; Straver, L. H.; Spek, A. L. (2008). J. Appl. Cryst. 41, 96-103).
;
_refine_ls_abs_structure_Flack   0.01(4)
_refine_ls_extinction_coef       0.00070(14)
_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   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         4465
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.213
_refine_ls_R_factor_all          0.0277
_refine_ls_R_factor_gt           0.0271
_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^)+(0.0430P)^2^+0.9443P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0738
_refine_ls_wR_factor_ref         0.0745
_reflns_Friedel_coverage         0.811
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.980
_reflns_number_gt                4385
_reflns_number_total             4465
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc05071g2.cif
_cod_data_source_block           Form-II
_cod_depositor_comments
'Adding full bibliography for 1560122--1560124.cif.'
_cod_database_code               1560123
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_refine_ls_abs_structure_hooft   0.04(3)
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C17) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.003
Uanis(C16) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.006
3.a Ternary CH refined with riding coordinates:
 N1(H1), C11(H11)
3.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C1(H1A,H1B), C19(H19A,H19B), C2(H2A,H2B), C21(H21A,H21B),
 C18(H18A,H18B), C16(H16A,H16B)
3.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C8(H8), C7(H7), C6(H6), C5(H5)
3.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C17(H17A,H17B,H17C)
3.e Idealised tetrahedral OH refined as rotating group:
 O5(H5A)
;
_shelx_res_checksum              53550
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.516
_oxdiff_exptl_absorpt_empirical_full_min 0.744