A General Strategy for Development of Single Benzene Fluorophore with Full-color-tunable, Environmentally Insensitive, and Two-photon Solid-State Emission
Yuan, Lin; Xiang, Zhen; Zhi-Yao, Wang; Ren, Tian-Bing; Wang, Xu; Liu, Yupeng; Zhang, Xingxing; Wu, Peng; Zhang, Xiaobing; Chemical Communications  (2019) –; doi:10.1039/C9CC06260B

data_7124077
_publ_section_title
;
 A General Strategy for Development of Single Benzene Fluorophore with
 Full-color-tunable, Environmentally Insensitive, and Two-photon
 Solid-State Emission
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC06260B
_journal_year                    2019
_chemical_formula_moiety         'C12 H12 F2 N4'
_chemical_formula_sum            'C12 H12 F2 N4'
_chemical_formula_weight         250.26
_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     direct
_audit_creation_date             2016-12-09
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_audit_update_record
;
2018-10-24 deposited with the CCDC.    2019-08-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.325(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.3349(6)
_cell_length_b                   7.6871(4)
_cell_length_c                   12.6994(6)
_cell_measurement_reflns_used    1655
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.5280
_cell_measurement_theta_min      3.5260
_cell_volume                     1196.82(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9981
_diffrn_measured_fraction_theta_max 0.8554
_diffrn_measurement_details
;
  1 omega  -40.00   27.00   1.0000    3.2500
omega____ theta____ kappa____ phi______ frames
    -      -14.9669   77.0000  -60.0000 67

  2 omega  -82.00    2.00   1.0000    3.2500
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -57.0000 -180.0000 84

  3 omega  -14.00   12.00   1.0000    3.2500
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -99.0000  -30.0000 26

  4 omega  -64.00  -38.00   1.0000    3.2500
omega____ theta____ kappa____ phi______ frames
    -      -14.9669 -178.0000  -60.0000 26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0500792000
_diffrn_orient_matrix_UB_12      0.0458364000
_diffrn_orient_matrix_UB_13      0.0019822000
_diffrn_orient_matrix_UB_21      0.0102127000
_diffrn_orient_matrix_UB_22      -0.0174240000
_diffrn_orient_matrix_UB_23      0.0550448000
_diffrn_orient_matrix_UB_31      0.0271090000
_diffrn_orient_matrix_UB_32      -0.0781886000
_diffrn_orient_matrix_UB_33      -0.0110997000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0157
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4909
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         3.103
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77317
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2446
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0450
_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^)+(0.0551P)^2^+0.2073P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1102
_refine_ls_wR_factor_ref         0.1243
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1737
_reflns_number_total             2446
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc06260b2.cif
_cod_data_source_block           161208_s3_zg
_cod_original_cell_volume        1196.83(10)
_cod_database_code               7124077
_chemical_oxdiff_formula         c12h12n2f2
_shelx_estimated_absorpt_t_max   0.958
_shelx_estimated_absorpt_t_min   0.958
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2.a Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'