Synthesis, characterization, aggregation-induced enhanced emission and solvatochromic behavior of dimethyl 4′-(diphenylamino)biphenyl-3,5-dicarboxylate: experimental and theoretical studies
Karaman, Merve; Demir, Nuriye; Bilgili, Hakan; Yakali, Gul; Gokpek, Yenal; Demic, Serafettin; Kaya, Nusret; Can, Mustafa; New Journal of Chemistry 44 (2020) 11498–11506; doi:10.1039/D0NJ01720E

data_7059692
_publ_section_title
;
 Synthesis, characterization, aggregation-induced enhanced emission and
 solvatochromic behavior of dimethyl
 4&#x2032;-(diphenylamino)biphenyl-3,5-dicarboxylate: experimental and
 theoretical studies
;
_journal_issue                   27
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              11498
_journal_page_last               11506
_journal_paper_doi               10.1039/D0NJ01720E
_journal_volume                  44
_journal_year                    2020
_chemical_formula_moiety         'C28 H23 N O4'
_chemical_formula_sum            'C28 H23 N O4'
_chemical_formula_weight         437.50
_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_Int_Tables_number      14
_audit_creation_date             2020-01-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-03-17 deposited with the CCDC.	2020-06-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.119(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.0275(14)
_cell_length_b                   26.058(2)
_cell_length_c                   9.7852(9)
_cell_measurement_reflns_used    1295
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      21.1920
_cell_measurement_theta_min      3.6410
_cell_volume                     2250.6(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0667
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9923
_diffrn_measured_fraction_theta_max 0.9923
_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     -3.00  91.00   1.00   20.19    --   20.23  57.00 120.00   94
  2  \w    -54.00  49.00   1.00   20.19    --  -22.26  37.00 -90.00  103
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0549078000
_diffrn_orient_matrix_UB_12      0.0179986000
_diffrn_orient_matrix_UB_13      -0.0117804000
_diffrn_orient_matrix_UB_21      -0.0576948000
_diffrn_orient_matrix_UB_22      0.0145681000
_diffrn_orient_matrix_UB_23      -0.0433854000
_diffrn_orient_matrix_UB_31      -0.0103424000
_diffrn_orient_matrix_UB_32      0.0143294000
_diffrn_orient_matrix_UB_33      0.0589594000
_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  0.0325
_diffrn_reflns_av_unetI/netI     0.0774
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            7287
_diffrn_reflns_theta_full        25.6781
_diffrn_reflns_theta_max         25.68
_diffrn_reflns_theta_min         3.13
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.964
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
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    1.2911
_exptl_crystal_description       prism
_exptl_crystal_F_000             920.4746
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.209
_exptl_crystal_size_min          0.185
_refine_diff_density_max         0.3182
_refine_diff_density_min         -0.4076
_refine_diff_density_rms         0.0903
_refine_ls_d_res_high            0.8201
_refine_ls_d_res_low             6.5145
_refine_ls_goodness_of_fit_ref   1.0124
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    42
_refine_ls_number_parameters     300
_refine_ls_number_reflns         4228
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0124
_refine_ls_R_factor_all          0.1286
_refine_ls_R_factor_gt           0.0581
_refine_ls_shift/su_max          0.0173
_refine_ls_shift/su_mean         0.0003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0403P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1036
_refine_ls_wR_factor_ref         0.1360
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              7
_reflns_limit_h_min              -10
_reflns_limit_k_max              31
_reflns_limit_k_min              0
_reflns_limit_l_max              11
_reflns_limit_l_min              -6
_reflns_number_gt                2237
_reflns_number_total             4228
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d0nj01720e2.cif
_cod_data_source_block           smart
_cod_depositor_comments
;Adding full bibliography for 7059692.cif.

 Adding full bibliography for 7059692.cif.
;
_cod_original_cell_volume        2250.5(5)
_cod_original_sg_symbol_Hall     '-P 2ybc (x-z,y,z)'
_cod_database_code               7059692
_chemical_oxdiff_formula         'C28 H23 N O4'
_reflns_odcompleteness_completeness 98.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.63
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11),
 C12(H12), C14(H14), C15(H15), C17(H17), C18(H18), C20(H20), C22(H22), C24(H24)
2.b Idealised Me refined as rotating group:
 C26(H26a,H26b,H26c), C28(H28a,H28b,H28c)
;
_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 1.134
_oxdiff_exptl_absorpt_empirical_full_min 0.934