Weak interactions but potent effect: tunable mechanoluminescence by adjusting intermolecular C-H···π interactions.
Xie, Zongliang; Yu, Tao; Chen, Junru; Ubba, Eethamukkala; Wang, Leyu; Mao, Zhu; Su, Tongtong; Zhang, Yi; Aldred, Matthew P.; Chi, Zhenguo; Chemical science 9 (2018) 5787–5794; doi:10.1039/c8sc01703d

data_1549498
_publ_section_title
;
 Weak interactions but potent effect: tunable mechanoluminescence by
 adjusting intermolecular C-H&#x00B7;&#x00B7;&#x00B7;\p interactions.
;
_journal_issue                   26
_journal_name_full               'Chemical science'
_journal_page_first              5787
_journal_page_last               5794
_journal_paper_doi               10.1039/c8sc01703d
_journal_volume                  9
_journal_year                    2018
_chemical_formula_moiety         'C37 H28 N O P'
_chemical_formula_sum            'C37 H28 N O P'
_chemical_formula_weight         533.57
_chemical_name_systematic        ONdP(GC)
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-11-26
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2017-11-26 deposited with the CCDC.
2018-06-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.573(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   23.584(4)
_cell_length_b                   6.0025(7)
_cell_length_c                   21.526(3)
_cell_measurement_reflns_used    3564
_cell_measurement_temperature    272(4)
_cell_measurement_theta_max      73.7840
_cell_measurement_theta_min      3.7830
_cell_volume                     2974.2(8)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_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      272(4)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2913
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.946
_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    -67.00  28.00   1.00    1.78    --  -40.50  57.00  30.00   95
  2  \w    -93.00  -2.00   1.00    1.78    --  -40.50 125.00 120.00   91
  3  \w     27.00  53.00   1.00    1.78    --   42.99-125.00 -60.00   26
  4  \w     36.00 130.00   1.00    7.14    --  107.32 -45.00-180.00   94
  5  \w    109.00 178.00   1.00    7.14    --  107.32  45.00-120.00   69
  6  \w     92.00 178.00   1.00    7.14    --  107.32  61.00 -30.00   86
  7  \w     26.00  91.00   1.00    7.14    --  107.32 -94.00  90.00   65
  8  \w     30.00  62.00   1.00    7.14    --  107.32 -94.00  30.00   32
  9  \w     21.00  47.00   1.00    1.78    --   42.99  37.00 -30.00   26
 10  \w     91.00 116.00   1.00    1.78    --   42.99  37.00 -30.00   25
 11  \w    131.00 142.00   1.00    7.14    --  107.32 125.00  90.00   11
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0500142000
_diffrn_orient_matrix_UB_12      0.1043502000
_diffrn_orient_matrix_UB_13      -0.0257590000
_diffrn_orient_matrix_UB_21      -0.0431452000
_diffrn_orient_matrix_UB_22      0.1625604000
_diffrn_orient_matrix_UB_23      -0.0410888000
_diffrn_orient_matrix_UB_31      0.0105934000
_diffrn_orient_matrix_UB_32      0.1690647000
_diffrn_orient_matrix_UB_33      0.0550551000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            4795
_diffrn_reflns_point_group_measured_fraction_full 0.633
_diffrn_reflns_point_group_measured_fraction_max 0.599
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.913
_diffrn_reflns_theta_min         3.841
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.036
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.29913
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.192
_exptl_crystal_description       plate
_exptl_crystal_F_000             1120
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane/n-hexane'
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.612
_refine_diff_density_min         -0.446
_refine_diff_density_rms         0.086
_refine_ls_abs_structure_details
;
 Flack x determined using 675 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.47(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.372
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         3619
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.371
_refine_ls_R_factor_all          0.0966
_refine_ls_R_factor_gt           0.0872
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2447
_refine_ls_wR_factor_ref         0.2916
_reflns_Friedel_coverage         0.266
_reflns_Friedel_fraction_full    0.280
_reflns_Friedel_fraction_max     0.252
_reflns_number_gt                3278
_reflns_number_total             3619
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8sc01703d2.cif
_cod_data_source_block           17070701
_cod_depositor_comments
'Adding full bibliography for 1549497--1549498.cif.'
_cod_original_cell_volume        2974.2(7)
_cod_database_code               1549498
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         CHNOP
_chemical_oxdiff_usercomment     ONdP-nH
_reflns_odcompleteness_completeness 98.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 O1-C1 \\sim O1A-C1
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(O1) = Uanis(O1A)
4. Others
 Sof(O1A)=1-FVAR(1)
 Sof(O1)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C25(H25), C7(H7), C24(H24), C4(H4), C13(H13), C6(H6), C34(H34), C27(H27),
 C21(H21), C3(H3), C22(H22), C35(H35), C36(H36), C33(H33), C19(H19), C18(H18),
 C12(H12), C31(H31), C29(H29), C17(H17), C30(H30), C16(H16), C9(H9), C11(H11),
 C15(H15), C10(H10), C28(H28), C37(H37)
;
_shelx_res_checksum              89183
_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 2.897
_oxdiff_exptl_absorpt_empirical_full_min 0.471