#------------------------------------------------------------------------------
#$Date: 2023-08-05 12:15:22 +0300 (Sat, 05 Aug 2023) $
#$Revision: 285476 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/25/7062517.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_7062517
loop_
_publ_author_name
'Wu, Dong-En'
'Guo, Qing-Hui'
_publ_section_title
;
 Evaluating the isomeric effects of donors on the structures and
 photophysical properties of donor--acceptor--π bridge--donor
 (D1--A--π--D2) prototype fluorophores
;
_journal_issue                   28
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              13409
_journal_page_last               13421
_journal_paper_doi               10.1039/D3NJ01845H
_journal_volume                  47
_journal_year                    2023
_chemical_formula_moiety         'C29 H20 N2 O'
_chemical_formula_sum            'C29 H20 N2 O'
_chemical_formula_weight         412.47
_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'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/ccdc.csd.cc2dy90p
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-12-24 deposited with the CCDC.	2023-06-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.533(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.6109(5)
_cell_length_b                   10.0070(4)
_cell_length_c                   23.2959(11)
_cell_measurement_reflns_used    4728
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.60
_cell_measurement_theta_min      2.31
_cell_volume                     2239.71(18)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 10.42
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0481
_diffrn_reflns_av_unetI/netI     0.0700
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            17698
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.475
_diffrn_reflns_theta_min         2.271
_diffrn_source.source            'Ius 2.0'
_diffrn_source.type              microfocus
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6589
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       0.012(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         5072
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.1455
_refine_ls_R_factor_gt           0.0598
_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)+(0.0597P)²+0.3787P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1270
_refine_ls_wR_factor_ref         0.1531
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2594
_reflns_number_total             5072
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3nj01845h2.cif
_cod_data_source_block           2021102510_a
_cod_depositor_comments
'Adding full bibliography for 7062514--7062517.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7062517
_shelx_shelxl_version_number     2018/3
_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   0.988
_shelx_estimated_absorpt_t_max   0.991
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
C1 C 0.6222(2) 0.45785(19) 0.59486(8) 0.0534(5) Uani 1 1 d . . . . .
C2 C 0.5593(2) 0.3288(2) 0.58260(9) 0.0620(6) Uani 1 1 d . . . . .
H2 H 0.586565 0.285429 0.549426 0.074 Uiso 1 1 calc R U . . .
C3 C 0.4665(2) 0.26687(19) 0.61437(9) 0.0558(5) Uani 1 1 d . . . . .
H3 H 0.444232 0.306180 0.649116 0.067 Uiso 1 1 calc R U . . .
C4 C 0.3962(2) 0.1412(2) 0.59891(9) 0.0631(6) Uani 1 1 d . . . . .
C5 C 0.3694(3) 0.1120(2) 0.54107(11) 0.0948(9) Uani 1 1 d . . . . .
H5 H 0.403569 0.168740 0.513138 0.114 Uiso 1 1 calc R U . . .
C6 C 0.2936(4) 0.0013(3) 0.52438(14) 0.1179(11) Uani 1 1 d . . . . .
H6 H 0.277181 -0.016787 0.485625 0.141 Uiso 1 1 calc R U . . .
C7 C 0.2424(4) -0.0823(3) 0.56554(17) 0.1178(12) Uani 1 1 d . . . . .
H7 H 0.189300 -0.156203 0.554686 0.141 Uiso 1 1 calc R U . . .
C8 C 0.2694(3) -0.0570(2) 0.62259(13) 0.0905(8) Uani 1 1 d . . . . .
H8 H 0.235652 -0.115726 0.649861 0.109 Uiso 1 1 calc R U . . .
C9 C 0.3455(2) 0.05354(19) 0.64080(10) 0.0648(6) Uani 1 1 d . . . . .
C10 C 0.3734(2) 0.07349(19) 0.70294(10) 0.0583(6) Uani 1 1 d . . . . .
C11 C 0.2682(3) 0.0538(3) 0.74205(14) 0.0875(8) Uani 1 1 d . . . . .
H11 H 0.180003 0.028338 0.728823 0.105 Uiso 1 1 calc R U . . .
C12 C 0.2931(3) 0.0714(3) 0.79996(14) 0.1010(10) Uani 1 1 d . . . . .
H12 H 0.221388 0.058117 0.825388 0.121 Uiso 1 1 calc R U . . .
C13 C 0.4215(3) 0.1080(2) 0.82051(11) 0.0846(8) Uani 1 1 d . . . . .
H13 H 0.436809 0.122145 0.859620 0.102 Uiso 1 1 calc R U . . .
C14 C 0.5274(3) 0.1238(2) 0.78328(10) 0.0664(6) Uani 1 1 d . . . . .
H14 H 0.615915 0.146453 0.797196 0.080 Uiso 1 1 calc R U . . .
C15 C 0.5038(2) 0.10627(18) 0.72485(9) 0.0572(5) Uani 1 1 d . . . . .
H15 H 0.577061 0.116757 0.699958 0.069 Uiso 1 1 calc R U . . .
C16 C 0.6046(2) 0.52523(18) 0.65093(8) 0.0501(5) Uani 1 1 d . . . . .
C17 C 0.5577(2) 0.65974(19) 0.65248(9) 0.0586(5) Uani 1 1 d . . . . .
H17 H 0.536541 0.704119 0.618269 0.070 Uiso 1 1 calc R U . . .
C18 C 0.5432(2) 0.72454(19) 0.70328(9) 0.0596(6) Uani 1 1 d . . . . .
H18 H 0.511948 0.812500 0.703169 0.072 Uiso 1 1 calc R U . . .
C19 C 0.57431(19) 0.66170(18) 0.75573(8) 0.0504(5) Uani 1 1 d . . . . .
C20 C 0.5551(2) 0.7259(2) 0.80953(9) 0.0619(6) Uani 1 1 d . . . . .
H20 H 0.523269 0.813582 0.810615 0.074 Uiso 1 1 calc R U . . .
C21 C 0.5831(2) 0.6593(2) 0.85902(9) 0.0682(6) Uani 1 1 d . . . . .
C22 C 0.6326(3) 0.5279(2) 0.85827(9) 0.0755(7) Uani 1 1 d . . . . .
H22 H 0.652660 0.483887 0.892669 0.091 Uiso 1 1 calc R U . . .
C23 C 0.6513(2) 0.4647(2) 0.80799(9) 0.0657(6) Uani 1 1 d . . . . .
H23 H 0.684455 0.377389 0.808208 0.079 Uiso 1 1 calc R U . . .
C24 C 0.62188(19) 0.52805(18) 0.75525(8) 0.0483(5) Uani 1 1 d . . . . .
C25 C 0.63528(19) 0.46296(18) 0.70173(8) 0.0513(5) Uani 1 1 d . . . . .
H25 H 0.666021 0.374855 0.701220 0.062 Uiso 1 1 calc R U . . .
C26 C 0.4841(3) 0.8215(3) 0.92006(12) 0.1089(10) Uani 1 1 d . . . . .
H26A H 0.527841 0.897033 0.902679 0.163 Uiso 1 1 calc R U . . .
H26B H 0.472561 0.838626 0.960200 0.163 Uiso 1 1 calc R U . . .
H26C H 0.394659 0.806533 0.901840 0.163 Uiso 1 1 calc R U . . .
C27 C 0.6977(2) 0.5188(2) 0.55397(8) 0.0594(6) Uani 1 1 d . . . . .
C28 C 0.7760(3) 0.6381(2) 0.56445(8) 0.0664(6) Uani 1 1 d . . . . .
C29 C 0.7110(3) 0.4660(2) 0.49719(10) 0.0720(7) Uani 1 1 d . . . . .
N1 N 0.8422(3) 0.7313(2) 0.57092(9) 0.0965(7) Uani 1 1 d . . . . .
N2 N 0.7223(3) 0.4274(2) 0.45161(10) 0.1018(8) Uani 1 1 d . . . . .
O1 O 0.5667(2) 0.70907(18) 0.91350(7) 0.0995(6) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
C27 C1 C2 119.30(18) . . ?
C27 C1 C16 119.30(17) . . ?
C2 C1 C16 121.39(18) . . ?
C3 C2 C1 126.03(19) . . ?
C3 C2 H2 117.0 . . ?
C1 C2 H2 117.0 . . ?
C2 C3 C4 125.1(2) . . ?
C2 C3 H3 117.5 . . ?
C4 C3 H3 117.5 . . ?
C5 C4 C9 118.7(2) . . ?
C5 C4 C3 119.2(2) . . ?
C9 C4 C3 121.94(19) . . ?
C6 C5 C4 121.6(3) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C7 C6 C5 119.3(3) . . ?
C7 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C8 C7 C6 120.2(3) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C7 C8 C9 121.9(3) . . ?
C7 C8 H8 119.1 . . ?
C9 C8 H8 119.1 . . ?
C8 C9 C4 118.3(2) . . ?
C8 C9 C10 119.2(2) . . ?
C4 C9 C10 122.47(19) . . ?
C15 C10 C11 117.3(2) . . ?
C15 C10 C9 122.2(2) . . ?
C11 C10 C9 120.4(2) . . ?
C12 C11 C10 120.9(3) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C13 C12 C11 120.7(3) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 119.5(3) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C13 C14 C15 120.3(2) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C10 C15 C14 121.1(2) . . ?
C10 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C25 C16 C17 118.22(17) . . ?
C25 C16 C1 121.97(17) . . ?
C17 C16 C1 119.79(16) . . ?
C18 C17 C16 120.93(18) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C17 C18 C19 121.41(18) . . ?
C17 C18 H18 119.3 . . ?
C19 C18 H18 119.3 . . ?
C18 C19 C24 118.68(17) . . ?
C18 C19 C20 122.40(18) . . ?
C24 C19 C20 118.88(17) . . ?
C21 C20 C19 120.04(19) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C21 O1 125.7(2) . . ?
C20 C21 C22 120.82(19) . . ?
O1 C21 C22 113.5(2) . . ?
C23 C22 C21 120.4(2) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C22 C23 C24 121.3(2) . . ?
C22 C23 H23 119.3 . . ?
C24 C23 H23 119.3 . . ?
C23 C24 C19 118.54(17) . . ?
C23 C24 C25 122.81(17) . . ?
C19 C24 C25 118.65(16) . . ?
C16 C25 C24 122.12(17) . . ?
C16 C25 H25 118.9 . . ?
C24 C25 H25 118.9 . . ?
O1 C26 H26A 109.5 . . ?
O1 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O1 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C1 C27 C28 122.98(18) . . ?
C1 C27 C29 122.99(19) . . ?
C28 C27 C29 113.96(18) . . ?
N1 C28 C27 176.9(3) . . ?
N2 C29 C27 178.2(2) . . ?
C21 O1 C26 118.3(2) . . ?
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
C1 C27 1.357(3) . ?
C1 C2 1.451(3) . ?
C1 C16 1.484(3) . ?
C2 C3 1.328(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.467(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.396(3) . ?
C4 C9 1.409(3) . ?
C5 C6 1.377(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.373(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.371(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.386(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.479(3) . ?
C10 C15 1.380(3) . ?
C10 C11 1.393(3) . ?
C11 C12 1.375(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.362(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.364(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.385(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C25 1.363(2) . ?
C16 C17 1.420(3) . ?
C17 C18 1.360(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.399(3) . ?
C18 H18 0.9300 . ?
C19 C24 1.414(3) . ?
C19 C20 1.425(3) . ?
C20 C21 1.352(3) . ?
C20 H20 0.9300 . ?
C21 O1 1.376(2) . ?
C21 C22 1.399(3) . ?
C22 C23 1.348(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.405(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.416(2) . ?
C25 H25 0.9300 . ?
C26 O1 1.388(3) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 C28 1.429(3) . ?
C27 C29 1.434(3) . ?
C28 N1 1.137(3) . ?
C29 N2 1.138(3) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C22 H22 N1 0.93 2.67 3.401(3) 136.4 2_646 yes
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
C27 C1 C2 C3 -169.1(2) . . . . ?
C16 C1 C2 C3 10.2(3) . . . . ?
C1 C2 C3 C4 175.02(19) . . . . ?
C2 C3 C4 C5 -31.1(3) . . . . ?
C2 C3 C4 C9 153.7(2) . . . . ?
C9 C4 C5 C6 0.9(4) . . . . ?
C3 C4 C5 C6 -174.5(3) . . . . ?
C4 C5 C6 C7 0.3(5) . . . . ?
C5 C6 C7 C8 -1.5(5) . . . . ?
C6 C7 C8 C9 1.4(5) . . . . ?
C7 C8 C9 C4 -0.2(4) . . . . ?
C7 C8 C9 C10 -178.7(2) . . . . ?
C5 C4 C9 C8 -0.9(3) . . . . ?
C3 C4 C9 C8 174.3(2) . . . . ?
C5 C4 C9 C10 177.6(2) . . . . ?
C3 C4 C9 C10 -7.2(3) . . . . ?
C8 C9 C10 C15 133.6(2) . . . . ?
C4 C9 C10 C15 -44.9(3) . . . . ?
C8 C9 C10 C11 -43.6(3) . . . . ?
C4 C9 C10 C11 137.9(2) . . . . ?
C15 C10 C11 C12 2.4(3) . . . . ?
C9 C10 C11 C12 179.7(2) . . . . ?
C10 C11 C12 C13 -0.3(4) . . . . ?
C11 C12 C13 C14 -1.8(4) . . . . ?
C12 C13 C14 C15 1.7(3) . . . . ?
C11 C10 C15 C14 -2.4(3) . . . . ?
C9 C10 C15 C14 -179.69(18) . . . . ?
C13 C14 C15 C10 0.4(3) . . . . ?
C27 C1 C16 C25 -127.3(2) . . . . ?
C2 C1 C16 C25 53.3(3) . . . . ?
C27 C1 C16 C17 51.1(3) . . . . ?
C2 C1 C16 C17 -128.3(2) . . . . ?
C25 C16 C17 C18 -0.3(3) . . . . ?
C1 C16 C17 C18 -178.74(18) . . . . ?
C16 C17 C18 C19 0.2(3) . . . . ?
C17 C18 C19 C24 0.1(3) . . . . ?
C17 C18 C19 C20 -177.63(19) . . . . ?
C18 C19 C20 C21 178.1(2) . . . . ?
C24 C19 C20 C21 0.4(3) . . . . ?
C19 C20 C21 O1 -178.9(2) . . . . ?
C19 C20 C21 C22 0.8(3) . . . . ?
C20 C21 C22 C23 -1.0(4) . . . . ?
O1 C21 C22 C23 178.7(2) . . . . ?
C21 C22 C23 C24 -0.1(4) . . . . ?
C22 C23 C24 C19 1.3(3) . . . . ?
C22 C23 C24 C25 -177.5(2) . . . . ?
C18 C19 C24 C23 -179.20(18) . . . . ?
C20 C19 C24 C23 -1.4(3) . . . . ?
C18 C19 C24 C25 -0.4(3) . . . . ?
C20 C19 C24 C25 177.41(17) . . . . ?
C17 C16 C25 C24 -0.1(3) . . . . ?
C1 C16 C25 C24 178.39(18) . . . . ?
C23 C24 C25 C16 179.14(19) . . . . ?
C19 C24 C25 C16 0.4(3) . . . . ?
C2 C1 C27 C28 -172.7(2) . . . . ?
C16 C1 C27 C28 7.9(3) . . . . ?
C2 C1 C27 C29 4.3(3) . . . . ?
C16 C1 C27 C29 -175.02(19) . . . . ?
C20 C21 O1 C26 17.1(4) . . . . ?
C22 C21 O1 C26 -162.5(2) . . . . ?
