Unconventional, Gram-Scale Synthesis of a Molecular Dimer Organic Luminogen with Aggregation-Induced Emission.
Meng, Peng; Han, Chenhui; Scully, Andrew D.; Xiao, Qi; Brock, Aidan J.; Hirai, Tadahiko; Skidmore, Melissa; McMurtrie, John C.; Chesman, Anthony S. R.; Xu, Jingsan; ACS applied materials & interfaces 13 (2021) 40441–40450; doi:10.1021/acsami.1c05841

data_4518956
_publ_section_title
;
 Unconventional, Gram-Scale Synthesis of a Molecular Dimer Organic
 Luminogen with Aggregation-Induced Emission.
;
_journal_issue                   34
_journal_name_full               'ACS applied materials &amp; interfaces'
_journal_page_first              40441
_journal_page_last               40450
_journal_paper_doi               10.1021/acsami.1c05841
_journal_volume                  13
_journal_year                    2021
_chemical_absolute_configuration unk
_chemical_formula_sum            'C19 H19 N9 O'
_chemical_formula_weight         389.43
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      33
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_creation_date             2021-03-12T13:34:10-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.5970(14)
_cell_length_b                   17.6854(19)
_cell_length_c                   7.1420(10)
_cell_measurement_reflns_used    741
_cell_measurement_temperature    190(2)
_cell_measurement_theta_max      21.83
_cell_measurement_theta_min      3.99
_cell_measurement_wavelength     0.71073
_cell_volume                     1843.7(4)
_computing_cell_refinement       'CrysalisPro (Agilent Technologies,     )'
_computing_data_collection       'CrysalisPro (Agilent Technologies,     )'
_computing_data_reduction        'CrysalisPro (Agilent Technologies,     )'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2015)'
_diffrn_ambient_temperature      190(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.02
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type
'Agilent Technologies Xcalibur, EosS2, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.035363
_diffrn_orient_matrix_UB_12      0.0601
_diffrn_orient_matrix_UB_13      0.012965
_diffrn_orient_matrix_UB_21      -0.008503
_diffrn_orient_matrix_UB_22      0.029105
_diffrn_orient_matrix_UB_23      -0.037702
_diffrn_orient_matrix_UB_31      -0.032218
_diffrn_orient_matrix_UB_32      -0.073533
_diffrn_orient_matrix_UB_33      -0.004338
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.039
_diffrn_reflns_av_unetI/netI     0.0907
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2564
_diffrn_reflns_point_group_measured_fraction_full 0.542
_diffrn_reflns_point_group_measured_fraction_max 0.542
_diffrn_reflns_reduction_process
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         3.378
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
No quotients, so Flack parameter determined by classical intensity fit
;
_refine_ls_abs_structure_Flack   5(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     264
_refine_ls_number_reflns         1763
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0926
_refine_ls_R_factor_gt           0.0601
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0521P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1242
_refine_ls_wR_factor_ref         0.1433
_reflns_Friedel_coverage         0
_reflns_Friedel_fraction_full    0
_reflns_Friedel_fraction_max     0
_reflns_number_gt                1228
_reflns_number_total             1763
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            am1c05841_si_002.cif
_cod_data_source_block           shelx
_cod_database_code               4518956
_shelx_estimated_absorpt_t_min   0.972
_shelx_estimated_absorpt_t_max   0.986
_shelx_shelxl_version_number     2018/1