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_1549497
_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(BC)
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-11-25
_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                 102.485(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.3348(9)
_cell_length_b                   5.9392(2)
_cell_length_c                   23.3779(10)
_cell_measurement_reflns_used    4174
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      72.9460
_cell_measurement_theta_min      3.8470
_cell_volume                     2892.2(2)
_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      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2913
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.955
_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    -87.00  14.00   1.00    1.00    --  -38.50   0.00-150.00  101
  2  \w     23.00  97.00   1.00    1.00    --   43.31-125.00 150.00   74
  3  \w     43.00 132.00   1.00    2.00    --  108.63 -77.00 -60.00   89
  4  \w    108.00 177.00   1.00    2.00    --  108.63  30.00 120.00   69
  5  \w    102.00 153.00   1.00    2.00    --  108.63 115.00 128.00   51
  6  \w     82.00 177.00   1.00    2.00    --  108.63  77.00  60.00   95
  7  \w     83.00 177.00   1.00    2.00    --  108.63  61.00-180.00   94
;
_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      -0.0281530000
_diffrn_orient_matrix_UB_12      0.2397641000
_diffrn_orient_matrix_UB_13      -0.0069552000
_diffrn_orient_matrix_UB_21      -0.0235901000
_diffrn_orient_matrix_UB_22      -0.0396195000
_diffrn_orient_matrix_UB_23      -0.0663031000
_diffrn_orient_matrix_UB_31      -0.0642237000
_diffrn_orient_matrix_UB_32      -0.0903852000
_diffrn_orient_matrix_UB_33      0.0105757000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10043
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.365
_diffrn_reflns_theta_min         3.873
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.065
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85280
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_description       prism
_exptl_crystal_F_000             1120
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane/methanol'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.23
_refine_diff_density_max         1.195
_refine_diff_density_min         -0.689
_refine_diff_density_rms         0.104
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     371
_refine_ls_number_reflns         5719
_refine_ls_number_restraints     73
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.1587
_refine_ls_R_factor_gt           0.1496
_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^)+(0.0632P)^2^+26.3920P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3314
_refine_ls_wR_factor_ref         0.3358
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5013
_reflns_number_total             5719
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8sc01703d2.cif
_cod_data_source_block           17070501
_cod_depositor_comments
'Adding full bibliography for 1549497--1549498.cif.'
_cod_database_code               1549497
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         CHNOP
_chemical_oxdiff_usercomment     ONdP-M
_shelx_estimated_absorpt_t_max   0.792
_shelx_estimated_absorpt_t_min   0.741
_reflns_odcompleteness_completeness 98.67
_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
 C18A-C17A \\sim C19-C18A \\sim C17-C16 \\sim C16-C15 \\sim C19-C14A \\sim
C19-C14 \\sim C16A-C15A ~
 C17A-C16A \\sim C18-C17 \\sim C15-C14 \\sim C15A-C14A
 with sigma of 0.02
 C31-C30 \\sim C31-C26 \\sim C27-C26 \\sim C28-C27 \\sim C29-C28 \\sim C30-C29
 with sigma of 0.02
3. Rigid bond restraints
 C30, C31, C26
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(C18A) = Uanis(C18) = Uanis(C17A) = Uanis(C17) = Uanis(C16A) = Uanis(C16)
= Uanis(C15) = Uanis(C15A) = Uanis(C14A) = Uanis(C14)
5. Others
 Sof(P2)=Sof(N2)=Sof(C18A)=Sof(H18A)=Sof(C17A)=Sof(H17A)=Sof(C16A)=Sof(H16A)=
 Sof(C15A)=Sof(H15A)=Sof(C14A)=Sof(H14A)=1-FVAR(1)
 Sof(P1)=Sof(C18)=Sof(H18)=Sof(N1)=Sof(C16)=Sof(H16)=Sof(C14)=Sof(H14)=
 Sof(C17)=Sof(H17)=Sof(C15)=Sof(H15)=FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 C21(H21), C7(H7), C25(H25), C22(H22), C9(H9), C27(H27), C24(H24), C3(H3),
 C6(H6), C37(H37), C11(H11), C12(H12), C18(H18), C30(H30), C34(H34), C35(H35),
 C4(H4), C13(H13), C33(H33), C10(H10), C31(H31), C16(H16), C36(H36), C28(H28),
 C29(H29), C14(H14), C17(H17), C15(H15), C18A(H18A), C17A(H17A), C16A(H16A),
 C15A(H15A), C14A(H14A)
;
_shelx_res_checksum              20750
_olex2_date_sample_data_collection 2017-07-05
_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 1.262
_oxdiff_exptl_absorpt_empirical_full_min 0.840