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#$Date: 2024-10-06 10:30:00 +0300 (Sun, 06 Oct 2024) $
#$Revision: 295214 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/92/7249232.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7249232
loop_
_publ_author_name
'Ravi, Sasikala'
'Priyadharsan, R. Rameshbabu'
'Karthikeyan, Subramanian'
'Pannipara, Mehboobali'
'Al-Sehemi, Abdullah G.'
'Moon, Dohyun'
'Anthony, Savarimuthu Philip'
_publ_section_title
;
 Self-reversible mechanofluorochromic AIEgens with tunable solid-state
 fluorescence: effect of acceptors and intermolecular interactions
;
_journal_issue                   37
_journal_name_full               CrystEngComm
_journal_page_first              5241
_journal_page_last               5248
_journal_paper_doi               10.1039/D4CE00729H
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         'C25 H20 N2 O3'
_chemical_formula_sum            'C25 H20 N2 O3'
_chemical_formula_weight         396.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2024-07-18 deposited with the CCDC.	2024-08-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 123.79(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.950(4)
_cell_length_b                   18.111(4)
_cell_length_c                   14.354(3)
_cell_measurement_reflns_used    57480
_cell_measurement_temperature    220(2)
_cell_measurement_theta_max      30.000
_cell_measurement_theta_min      0.361
_cell_volume                     3878(2)
_computing_cell_refinement       'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_data_collection
'PAL BL2D-SMDC Program(Shin et.al, 2016)'
_computing_data_reduction        'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'DIAMOND 4(Putx&Brandenburg, 2014)'
_computing_publication_material  'publCIF(Westrip, 2010)'
_computing_structure_refinement  'SHELXL-2018(Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2018(Sheldrick, 2018)'
_diffrn_ambient_temperature      220(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'Rayonix SX165 CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.630
_diffrn_reflns_av_R_equivalents  0.0549
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            20192
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        22.210
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         1.568
_diffrn_source                   'PLSII 2D bending magnet'
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.980
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
'HKL3000sm Scalepack(Otwinowski et.al,2003)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_description       block
_exptl_crystal_F_000             1664
_exptl_crystal_size_max          0.051
_exptl_crystal_size_mid          0.038
_exptl_crystal_size_min          0.029
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       0.0120(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         5296
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0454
_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/[σ²(Fo²)+(0.0647P)²+0.7741P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1152
_refine_ls_wR_factor_ref         0.1241
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3992
_reflns_number_total             5296
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ce00729h2.cif
_cod_data_source_block           SPA937
_cod_depositor_comments
'Adding full bibliography for 7249231--7249233.cif.'
_cod_original_cell_volume        3877.9(18)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7249232
_shelx_shelxl_version_number     2019/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.996
_shelx_estimated_absorpt_t_max   0.998
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.54744(8) 0.07829(5) 0.49269(8) 0.0386(2) Uani 1 1 d . . . . .
O2 O 0.17619(7) 0.59846(6) 0.31678(10) 0.0435(3) Uani 1 1 d . . . . .
O3 O 0.25641(6) 0.70260(5) 0.38652(8) 0.0324(2) Uani 1 1 d . . . . .
N1 N 0.58712(7) 0.29919(5) 0.70495(8) 0.0252(2) Uani 1 1 d . . . . .
N2 N 0.46613(9) 0.67149(7) 0.59944(11) 0.0425(3) Uani 1 1 d . . . . .
C1 C 0.53568(13) 0.12101(9) 0.40341(12) 0.0479(4) Uani 1 1 d . . . . .
H1A H 0.529939 0.088641 0.345907 0.072 Uiso 1 1 calc R U . . .
H1B H 0.587117 0.153095 0.430772 0.072 Uiso 1 1 calc R U . . .
H1C H 0.481890 0.150717 0.372066 0.072 Uiso 1 1 calc R U . . .
C2 C 0.56534(8) 0.11403(6) 0.58596(10) 0.0259(2) Uani 1 1 d . . . . .
C3 C 0.56407(8) 0.19023(6) 0.59458(10) 0.0241(2) Uani 1 1 d . . . . .
H3 H 0.548300 0.220529 0.533036 0.029 Uiso 1 1 calc R U . . .
C4 C 0.58642(8) 0.22093(6) 0.69538(10) 0.0238(2) Uani 1 1 d . . . . .
C5 C 0.60993(9) 0.17745(7) 0.78669(11) 0.0287(3) Uani 1 1 d . . . . .
H5 H 0.625587 0.198980 0.854907 0.034 Uiso 1 1 calc R U . . .
C6 C 0.61004(9) 0.10126(7) 0.77601(11) 0.0309(3) Uani 1 1 d . . . . .
H6 H 0.625466 0.071041 0.837510 0.037 Uiso 1 1 calc R U . . .
C7 C 0.58793(9) 0.06933(7) 0.67678(11) 0.0306(3) Uani 1 1 d . . . . .
H7 H 0.588093 0.017684 0.670440 0.037 Uiso 1 1 calc R U . . .
C8 C 0.66144(8) 0.34152(6) 0.78083(10) 0.0236(2) Uani 1 1 d . . . . .
C9 C 0.74753(8) 0.31863(7) 0.86359(11) 0.0295(3) Uani 1 1 d . . . . .
H9 H 0.762517 0.268273 0.877052 0.035 Uiso 1 1 calc R U . . .
C10 C 0.81023(9) 0.37288(8) 0.92532(11) 0.0327(3) Uani 1 1 d . . . . .
H10 H 0.869155 0.359016 0.981546 0.039 Uiso 1 1 calc R U . . .
C11 C 0.78841(9) 0.44756(8) 0.90641(11) 0.0346(3) Uani 1 1 d . . . . .
H11 H 0.832427 0.483222 0.950125 0.042 Uiso 1 1 calc R U . . .
C12 C 0.70279(9) 0.46957(7) 0.82411(11) 0.0310(3) Uani 1 1 d . . . . .
H12 H 0.688152 0.520012 0.811369 0.037 Uiso 1 1 calc R U . . .
C13 C 0.63843(8) 0.41644(6) 0.76027(10) 0.0235(2) Uani 1 1 d . . . . .
C14 C 0.54560(8) 0.41966(6) 0.66735(10) 0.0223(2) Uani 1 1 d . . . . .
C15 C 0.48692(8) 0.47730(6) 0.61060(10) 0.0250(2) Uani 1 1 d . . . . .
H15 H 0.505919 0.526441 0.631216 0.030 Uiso 1 1 calc R U . . .
C16 C 0.39893(8) 0.46170(6) 0.52212(10) 0.0245(2) Uani 1 1 d . . . . .
C17 C 0.37261(8) 0.38720(6) 0.49313(11) 0.0268(3) Uani 1 1 d . . . . .
H17 H 0.313357 0.376976 0.433749 0.032 Uiso 1 1 calc R U . . .
C18 C 0.42997(8) 0.32921(6) 0.54805(10) 0.0266(3) Uani 1 1 d . . . . .
H18 H 0.411164 0.280066 0.527139 0.032 Uiso 1 1 calc R U . . .
C19 C 0.51699(8) 0.34604(6) 0.63585(10) 0.0227(2) Uani 1 1 d . . . . .
C20 C 0.33057(9) 0.51619(7) 0.45735(11) 0.0272(2) Uani 1 1 d . . . . .
H20 H 0.274945 0.496075 0.401263 0.033 Uiso 1 1 calc R U . . .
C21 C 0.33121(8) 0.59067(7) 0.46189(10) 0.0261(2) Uani 1 1 d . . . . .
C22 C 0.40658(9) 0.63490(7) 0.53817(11) 0.0290(3) Uani 1 1 d . . . . .
C23 C 0.24576(9) 0.62944(7) 0.38005(11) 0.0288(3) Uani 1 1 d . . . . .
C24 C 0.17584(9) 0.74455(7) 0.30901(13) 0.0353(3) Uani 1 1 d . . . . .
H24A H 0.131981 0.739307 0.328899 0.042 Uiso 1 1 calc R U . . .
H24B H 0.148732 0.726349 0.232364 0.042 Uiso 1 1 calc R U . . .
C25 C 0.20220(10) 0.82363(7) 0.31667(14) 0.0408(3) Uani 1 1 d . . . . .
H25A H 0.149137 0.853288 0.268545 0.061 Uiso 1 1 calc R U . . .
H25B H 0.243057 0.828580 0.292897 0.061 Uiso 1 1 calc R U . . .
H25C H 0.231516 0.840402 0.393549 0.061 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0021 0.0012 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0044 0.0025 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0080 0.0047 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C1 118.02(11) . . ?
C23 O3 C24 114.98(10) . . ?
C19 N1 C8 108.56(10) . . ?
C19 N1 C4 126.02(10) . . ?
C8 N1 C4 125.25(10) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 123.84(11) . . ?
O1 C2 C7 115.71(11) . . ?
C3 C2 C7 120.44(11) . . ?
C4 C3 C2 118.89(11) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C5 C4 C3 121.44(11) . . ?
C5 C4 N1 119.70(11) . . ?
C3 C4 N1 118.85(10) . . ?
C4 C5 C6 118.75(12) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C7 C6 C5 120.99(11) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C2 119.49(11) . . ?
C6 C7 H7 120.3 . . ?
C2 C7 H7 120.3 . . ?
C9 C8 N1 129.13(11) . . ?
C9 C8 C13 121.77(11) . . ?
N1 C8 C13 109.06(10) . . ?
C10 C9 C8 117.28(12) . . ?
C10 C9 H9 121.4 . . ?
C8 C9 H9 121.4 . . ?
C9 C10 C11 121.70(13) . . ?
C9 C10 H10 119.1 . . ?
C11 C10 H10 119.1 . . ?
C12 C11 C10 120.47(12) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 119.22(12) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 H12 120.4 . . ?
C12 C13 C8 119.55(12) . . ?
C12 C13 C14 133.75(11) . . ?
C8 C13 C14 106.68(10) . . ?
C15 C14 C19 120.22(11) . . ?
C15 C14 C13 133.20(11) . . ?
C19 C14 C13 106.58(10) . . ?
C14 C15 C16 119.23(11) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
C15 C16 C17 118.94(10) . . ?
C15 C16 C20 125.04(11) . . ?
C17 C16 C20 116.02(11) . . ?
C18 C17 C16 122.72(12) . . ?
C18 C17 H17 118.6 . . ?
C16 C17 H17 118.6 . . ?
C17 C18 C19 117.33(11) . . ?
C17 C18 H18 121.3 . . ?
C19 C18 H18 121.3 . . ?
N1 C19 C18 129.33(11) . . ?
N1 C19 C14 109.11(10) . . ?
C18 C19 C14 121.56(10) . . ?
C21 C20 C16 132.22(12) . . ?
C21 C20 H20 113.9 . . ?
C16 C20 H20 113.9 . . ?
C20 C21 C22 125.36(12) . . ?
C20 C21 C23 117.08(12) . . ?
C22 C21 C23 117.56(11) . . ?
N2 C22 C21 178.69(14) . . ?
O2 C23 O3 124.46(12) . . ?
O2 C23 C21 123.94(12) . . ?
O3 C23 C21 111.60(11) . . ?
O3 C24 C25 107.77(11) . . ?
O3 C24 H24A 110.2 . . ?
C25 C24 H24A 110.2 . . ?
O3 C24 H24B 110.2 . . ?
C25 C24 H24B 110.2 . . ?
H24A C24 H24B 108.5 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.3550(15) . ?
O1 C1 1.4087(18) . ?
O2 C23 1.1990(17) . ?
O3 C23 1.3346(15) . ?
O3 C24 1.4548(16) . ?
N1 C19 1.3781(15) . ?
N1 C8 1.3919(16) . ?
N1 C4 1.4234(15) . ?
N2 C22 1.1443(19) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 H1C 0.9700 . ?
C2 C3 1.3869(16) . ?
C2 C7 1.3896(17) . ?
C3 C4 1.3848(17) . ?
C3 H3 0.9400 . ?
C4 C5 1.3787(17) . ?
C5 C6 1.3885(17) . ?
C5 H5 0.9400 . ?
C6 C7 1.3753(19) . ?
C6 H6 0.9400 . ?
C7 H7 0.9400 . ?
C8 C9 1.3890(18) . ?
C8 C13 1.4011(16) . ?
C9 C10 1.3811(18) . ?
C9 H9 0.9400 . ?
C10 C11 1.392(2) . ?
C10 H10 0.9400 . ?
C11 C12 1.377(2) . ?
C11 H11 0.9400 . ?
C12 C13 1.3865(17) . ?
C12 H12 0.9400 . ?
C13 C14 1.4445(18) . ?
C14 C15 1.3814(16) . ?
C14 C19 1.4098(15) . ?
C15 C16 1.3986(18) . ?
C15 H15 0.9400 . ?
C16 C17 1.4136(16) . ?
C16 C20 1.4404(16) . ?
C17 C18 1.3717(16) . ?
C17 H17 0.9400 . ?
C18 C19 1.3897(18) . ?
C18 H18 0.9400 . ?
C20 C21 1.3502(17) . ?
C20 H20 0.9400 . ?
C21 C22 1.4224(19) . ?
C21 C23 1.4903(18) . ?
C24 C25 1.4930(19) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C25 H25C 0.9700 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 O1 C2 C3 6.60(19) . . . . ?
C1 O1 C2 C7 -171.88(13) . . . . ?
O1 C2 C3 C4 -177.86(12) . . . . ?
C7 C2 C3 C4 0.56(18) . . . . ?
C2 C3 C4 C5 0.15(18) . . . . ?
C2 C3 C4 N1 178.55(11) . . . . ?
C19 N1 C4 C5 -126.56(14) . . . . ?
C8 N1 C4 C5 58.69(17) . . . . ?
C19 N1 C4 C3 55.00(17) . . . . ?
C8 N1 C4 C3 -119.74(13) . . . . ?
C3 C4 C5 C6 -0.69(19) . . . . ?
N1 C4 C5 C6 -179.08(12) . . . . ?
C4 C5 C6 C7 0.5(2) . . . . ?
C5 C6 C7 C2 0.2(2) . . . . ?
O1 C2 C7 C6 177.83(12) . . . . ?
C3 C2 C7 C6 -0.71(19) . . . . ?
C19 N1 C8 C9 -177.76(13) . . . . ?
C4 N1 C8 C9 -2.2(2) . . . . ?
C19 N1 C8 C13 0.24(14) . . . . ?
C4 N1 C8 C13 175.75(11) . . . . ?
N1 C8 C9 C10 177.67(13) . . . . ?
C13 C8 C9 C10 -0.11(19) . . . . ?
C8 C9 C10 C11 0.4(2) . . . . ?
C9 C10 C11 C12 -0.4(2) . . . . ?
C10 C11 C12 C13 0.1(2) . . . . ?
C11 C12 C13 C8 0.3(2) . . . . ?
C11 C12 C13 C14 -177.63(13) . . . . ?
C9 C8 C13 C12 -0.24(19) . . . . ?
N1 C8 C13 C12 -178.42(11) . . . . ?
C9 C8 C13 C14 178.17(11) . . . . ?
N1 C8 C13 C14 -0.01(14) . . . . ?
C12 C13 C14 C15 -2.0(2) . . . . ?
C8 C13 C14 C15 179.90(13) . . . . ?
C12 C13 C14 C19 177.87(14) . . . . ?
C8 C13 C14 C19 -0.21(13) . . . . ?
C19 C14 C15 C16 0.30(18) . . . . ?
C13 C14 C15 C16 -179.83(13) . . . . ?
C14 C15 C16 C17 -0.14(18) . . . . ?
C14 C15 C16 C20 178.82(11) . . . . ?
C15 C16 C17 C18 -0.19(19) . . . . ?
C20 C16 C17 C18 -179.24(12) . . . . ?
C16 C17 C18 C19 0.34(19) . . . . ?
C8 N1 C19 C18 -179.92(13) . . . . ?
C4 N1 C19 C18 4.6(2) . . . . ?
C8 N1 C19 C14 -0.38(14) . . . . ?
C4 N1 C19 C14 -175.85(11) . . . . ?
C17 C18 C19 N1 179.32(12) . . . . ?
C17 C18 C19 C14 -0.18(18) . . . . ?
C15 C14 C19 N1 -179.73(11) . . . . ?
C13 C14 C19 N1 0.36(13) . . . . ?
C15 C14 C19 C18 -0.14(18) . . . . ?
C13 C14 C19 C18 179.95(11) . . . . ?
C15 C16 C20 C21 0.4(2) . . . . ?
C17 C16 C20 C21 179.41(13) . . . . ?
C16 C20 C21 C22 0.4(2) . . . . ?
C16 C20 C21 C23 -179.61(13) . . . . ?
C24 O3 C23 O2 -0.36(19) . . . . ?
C24 O3 C23 C21 179.95(11) . . . . ?
C20 C21 C23 O2 5.3(2) . . . . ?
C22 C21 C23 O2 -174.71(13) . . . . ?
C20 C21 C23 O3 -175.00(11) . . . . ?
C22 C21 C23 O3 4.98(16) . . . . ?
C23 O3 C24 C25 -172.52(12) . . . . ?
