Two-Photon-Excited Ultralong Organic Room Temperature Phosphorescence by Operating Dual-Channel Triplet Harvesting
Mao, Zhu; Zhang, Yi; Yang, Zhan; Xu, Chao; Xie, Zongliang; Jiang, Long; Gu, Feng Long; Zhao, Juan; Aldred, Matthew Phillip; Chi, Zhenguo; Chemical Science  (2019) –; doi:10.1039/C9SC02282A

data_1551872
_publ_section_title
;
 Two-Photon-Excited Ultralong Organic Room Temperature Phosphorescence by
 Operating Dual-Channel Triplet Harvesting
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C9SC02282A
_journal_year                    2019
_chemical_compound_source        hexane
_chemical_formula_moiety         'C25 H17 N O'
_chemical_formula_sum            'C25 H17 N O'
_chemical_formula_weight         347.39
_chemical_melting_point          427.15
_chemical_name_systematic        o-Cz
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-09-12
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_audit_update_record
;
2018-12-15 deposited with the CCDC.    2019-06-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.1930(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.5634(2)
_cell_length_b                   15.7484(2)
_cell_length_c                   10.0607(2)
_cell_measurement_reflns_used    7587
_cell_measurement_temperature    275(6)
_cell_measurement_theta_max      74.0200
_cell_measurement_theta_min      5.2340
_cell_volume                     1821.41(5)
_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      air
_diffrn_ambient_temperature      275(6)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2913
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.981
_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    -34.00  82.00   1.00    1.78    --   41.89 -19.00 120.00  116
  2  \w     26.00  94.00   1.00    7.11    --  107.79 -94.00 120.00   68
  3  \w     77.00 109.00   1.00    7.11    --  107.79 -94.00 150.00   32
  4  \w     49.00 115.00   1.00    7.11    --  107.79 -45.00  90.00   66
  5  \w     73.00 107.00   1.00    7.11    --  107.79 -94.00  30.00   34
  6  \w     60.00 108.00   1.00    7.11    --  107.79 -94.00 -30.00   48
  7  \w     79.00 106.00   1.00    7.11    --  107.79 -94.00-120.00   27
  8  \w     35.00  62.00   1.00    7.11    --  107.79 -94.00-120.00   27
  9  \w     25.00  82.00   1.00    7.11    --  107.79 -94.00 -90.00   57
 10  \w     36.00 124.00   1.00    7.11    --  107.79 -45.00 -90.00   88
 11  \w     94.00 178.00   1.00    7.11    --  107.79  30.00-120.00   84
 12  \w    126.00 168.00   1.00    7.11    --  107.79  77.00  60.00   42
 13  \w    116.00 169.00   1.00    7.11    --  107.79 116.00 179.00   53
 14  \w      2.00  83.00   1.00    1.78    --   41.89 -99.00 150.00   81
 15  \w     24.00  73.00   1.00    1.78    --   41.89-125.00  90.00   49
 16  \w      3.00  29.00   1.00    1.78    --   41.89 -99.00  60.00   26
 17  \w     66.00 172.00   1.00    7.11    --  107.79  15.00-180.00  106
 18  \w   -118.00  -9.00   1.00    1.78    --  -41.89 -77.00 -60.00  109
;
_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      -0.0879864000
_diffrn_orient_matrix_UB_12      -0.0595847000
_diffrn_orient_matrix_UB_13      0.0572813000
_diffrn_orient_matrix_UB_21      -0.0782379000
_diffrn_orient_matrix_UB_22      0.0766764000
_diffrn_orient_matrix_UB_23      0.0227498000
_diffrn_orient_matrix_UB_31      -0.0639842000
_diffrn_orient_matrix_UB_32      -0.0117880000
_diffrn_orient_matrix_UB_33      -0.1411571000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_unetI/netI     0.0159
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11841
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.172
_diffrn_reflns_theta_min         3.845
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.601
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90644
_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    1.267
_exptl_crystal_description       prism
_exptl_crystal_F_000             728
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DCM'
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.134
_refine_diff_density_rms         0.027
_refine_ls_extinction_coef       0.0032(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3644
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0390
_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^)+(0.0680P)^2^+0.1600P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1168
_refine_ls_wR_factor_ref         0.1203
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3335
_reflns_number_total             3644
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc02282a2.cif
_cod_data_source_block           17091202
_cod_database_code               1551872
_chemical_oxdiff_formula         'C H O N'
_chemical_oxdiff_usercomment     2CzCH
_reflns_odcompleteness_completeness 99.85
_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.a Aromatic/amide H refined with riding coordinates:
 C009(H009), C00B(H00B), C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G),
 C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M),
 C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R)
;
_shelx_shelxl_version_number     2014/7
_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 1.528
_oxdiff_exptl_absorpt_empirical_full_min 0.722