#------------------------------------------------------------------------------
#$Date: 2023-08-05 12:15:22 +0300 (Sat, 05 Aug 2023) $
#$Revision: 285476 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/25/7062515.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_7062515
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         'C16 H12 N2 O'
_chemical_formula_sum            'C16 H12 N2 O'
_chemical_formula_weight         248.28
_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.cc2dy8wj
_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                 103.442(17)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.021(6)
_cell_length_b                   7.962(4)
_cell_length_c                   15.851(8)
_cell_measurement_reflns_used    4636
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.88
_cell_measurement_theta_min      2.55
_cell_volume                     1352.8(12)
_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-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.983
_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  0.0388
_diffrn_reflns_av_unetI/netI     0.0397
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13108
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.595
_diffrn_reflns_theta_min         2.554
_diffrn_source.source            'Ius 2.0'
_diffrn_source.type              microfocus
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6759
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.280
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         3095
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0950
_refine_ls_R_factor_gt           0.0536
_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)+(0.0833P)²+0.1169P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1379
_refine_ls_wR_factor_ref         0.1586
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1928
_reflns_number_total             3095
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3nj01845h2.cif
_cod_data_source_block           2020040503_a
_cod_depositor_comments
'Adding full bibliography for 7062514--7062517.cif.'
_cod_original_cell_volume        1352.8(11)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7062515
_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   0.973
_shelx_estimated_absorpt_t_max   0.979
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 0.27706(14) 0.44340(18) 0.71453(10) 0.0485(4) Uani 1 1 d . . . . .
C2 C 0.32825(15) 0.41323(19) 0.80374(10) 0.0525(4) Uani 1 1 d . . . . .
H2 H 0.277346 0.372558 0.838411 0.063 Uiso 1 1 calc R U . . .
C3 C 0.45088(15) 0.44301(19) 0.83930(10) 0.0525(4) Uani 1 1 d . . . . .
H3 H 0.482700 0.419573 0.897742 0.063 Uiso 1 1 calc R U . . .
C4 C 0.53156(14) 0.50878(17) 0.78975(9) 0.0464(4) Uani 1 1 d . . . . .
C5 C 0.65823(14) 0.54696(19) 0.82689(10) 0.0522(4) Uani 1 1 d . . . . .
H5 H 0.691523 0.525968 0.885414 0.063 Uiso 1 1 calc R U . . .
C6 C 0.73155(15) 0.6144(2) 0.77714(11) 0.0548(4) Uani 1 1 d . . . . .
C7 C 0.68308(16) 0.6434(2) 0.68814(11) 0.0616(5) Uani 1 1 d . . . . .
H7 H 0.734375 0.687137 0.654517 0.074 Uiso 1 1 calc R U . . .
C8 C 0.56195(15) 0.6080(2) 0.65098(10) 0.0571(4) Uani 1 1 d . . . . .
H8 H 0.531147 0.628365 0.592110 0.069 Uiso 1 1 calc R U . . .
C9 C 0.48146(14) 0.54046(18) 0.70058(10) 0.0478(4) Uani 1 1 d . . . . .
C10 C 0.35448(13) 0.50619(19) 0.66481(9) 0.0499(4) Uani 1 1 d . . . . .
H10 H 0.321833 0.526375 0.606129 0.060 Uiso 1 1 calc R U . . .
C11 C 0.14397(14) 0.41471(18) 0.67577(11) 0.0519(4) Uani 1 1 d . . . . .
C12 C 0.05019(16) 0.4748(2) 0.72431(13) 0.0718(5) Uani 1 1 d . . . . .
H12A H -0.032090 0.442865 0.693287 0.108 Uiso 1 1 calc R U . . .
H12B H 0.054790 0.594917 0.729601 0.108 Uiso 1 1 calc R U . . .
H12C H 0.067972 0.425168 0.781039 0.108 Uiso 1 1 calc R U . . .
C13 C 0.90634(18) 0.6411(3) 0.89685(14) 0.0885(7) Uani 1 1 d . . . . .
H13A H 0.857031 0.702450 0.928968 0.133 Uiso 1 1 calc R U . . .
H13B H 0.989933 0.684395 0.910176 0.133 Uiso 1 1 calc R U . . .
H13C H 0.907741 0.524486 0.912384 0.133 Uiso 1 1 calc R U . . .
C14 C 0.10606(14) 0.3389(2) 0.59748(11) 0.0551(4) Uani 1 1 d . . . . .
C15 C 0.18994(16) 0.2624(2) 0.55226(11) 0.0639(5) Uani 1 1 d . . . . .
C16 C -0.02341(18) 0.3248(2) 0.55335(12) 0.0666(5) Uani 1 1 d . . . . .
N1 N 0.25346(17) 0.1952(3) 0.51534(12) 0.0916(6) Uani 1 1 d . . . . .
N2 N -0.12566(16) 0.3152(2) 0.51605(12) 0.0909(6) Uani 1 1 d . . . . .
O1 O 0.85370(10) 0.65889(17) 0.80690(8) 0.0728(4) 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
C10 C1 C2 118.37(14) . . ?
C10 C1 C11 120.38(14) . . ?
C2 C1 C11 121.21(13) . . ?
C3 C2 C1 120.77(14) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 121.77(14) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C9 C4 C5 119.65(14) . . ?
C9 C4 C3 118.05(14) . . ?
C5 C4 C3 122.28(14) . . ?
C6 C5 C4 120.24(15) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 O1 124.86(15) . . ?
C5 C6 C7 120.45(15) . . ?
O1 C6 C7 114.69(14) . . ?
C8 C7 C6 120.46(15) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 C9 121.06(15) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
C10 C9 C4 119.18(13) . . ?
C10 C9 C8 122.69(14) . . ?
C4 C9 C8 118.12(14) . . ?
C1 C10 C9 121.83(14) . . ?
C1 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
C14 C11 C1 121.12(14) . . ?
C14 C11 C12 120.54(15) . . ?
C1 C11 C12 118.32(15) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 C15 123.40(15) . . ?
C11 C14 C16 122.61(16) . . ?
C15 C14 C16 113.97(16) . . ?
N1 C15 C14 176.9(2) . . ?
N2 C16 C14 178.02(19) . . ?
C6 O1 C13 117.52(14) . . ?
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 C10 1.383(2) . ?
C1 C2 1.416(2) . ?
C1 C11 1.470(2) . ?
C2 C3 1.359(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.416(2) . ?
C3 H3 0.9300 . ?
C4 C9 1.416(2) . ?
C4 C5 1.416(2) . ?
C5 C6 1.363(2) . ?
C5 H5 0.9300 . ?
C6 O1 1.366(2) . ?
C6 C7 1.407(2) . ?
C7 C8 1.358(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.421(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.409(2) . ?
C10 H10 0.9300 . ?
C11 C14 1.356(2) . ?
C11 C12 1.503(2) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 O1 1.416(2) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.431(3) . ?
C14 C16 1.440(2) . ?
C15 N1 1.145(2) . ?
C16 N2 1.147(2) . ?
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
C5 H5 N1 0.93 2.67 3.505(3) 149.0 4_666 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
C10 C1 C2 C3 -0.9(2) . . . . ?
C11 C1 C2 C3 -178.80(14) . . . . ?
C1 C2 C3 C4 1.6(2) . . . . ?
C2 C3 C4 C9 -1.2(2) . . . . ?
C2 C3 C4 C5 177.28(14) . . . . ?
C9 C4 C5 C6 0.2(2) . . . . ?
C3 C4 C5 C6 -178.21(14) . . . . ?
C4 C5 C6 O1 178.57(14) . . . . ?
C4 C5 C6 C7 -1.4(2) . . . . ?
C5 C6 C7 C8 1.4(3) . . . . ?
O1 C6 C7 C8 -178.52(15) . . . . ?
C6 C7 C8 C9 -0.3(3) . . . . ?
C5 C4 C9 C10 -178.32(12) . . . . ?
C3 C4 C9 C10 0.2(2) . . . . ?
C5 C4 C9 C8 0.9(2) . . . . ?
C3 C4 C9 C8 179.37(13) . . . . ?
C7 C8 C9 C10 178.32(15) . . . . ?
C7 C8 C9 C4 -0.8(2) . . . . ?
C2 C1 C10 C9 -0.1(2) . . . . ?
C11 C1 C10 C9 177.83(13) . . . . ?
C4 C9 C10 C1 0.4(2) . . . . ?
C8 C9 C10 C1 -178.75(14) . . . . ?
C10 C1 C11 C14 45.0(2) . . . . ?
C2 C1 C11 C14 -137.20(16) . . . . ?
C10 C1 C11 C12 -133.79(16) . . . . ?
C2 C1 C11 C12 44.0(2) . . . . ?
C1 C11 C14 C15 8.3(2) . . . . ?
C12 C11 C14 C15 -172.92(15) . . . . ?
C1 C11 C14 C16 -173.18(14) . . . . ?
C12 C11 C14 C16 5.6(2) . . . . ?
C5 C6 O1 C13 -3.2(3) . . . . ?
C7 C6 O1 C13 176.76(16) . . . . ?
