#------------------------------------------------------------------------------
#$Date: 2024-05-05 06:53:01 +0300 (Sun, 05 May 2024) $
#$Revision: 291680 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/30/7063095.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_7063095
loop_
_publ_author_name
'Ali, Irshad'
'Dwivedi, Bhupendra Kumar'
'Singh, Vishwa Deepak'
'Pandey, Daya Shankar'
_publ_section_title
;
 Intermolecular hydrogen bonding-assisted aggregation induced emission in
 quinolone--quinazoline conjugates and their potential use in
 acidochromism
;
_journal_issue                   15
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              6943
_journal_page_last               6953
_journal_paper_doi               10.1039/D3NJ05832H
_journal_volume                  48
_journal_year                    2024
_chemical_formula_moiety         'C23 H15 N3 O'
_chemical_formula_sum            'C23 H15 N3 O'
_chemical_formula_weight         350.380
_chemical_name_systematic        DSIA
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_atom_sites_solution_primary     iterative
_audit_creation_date             2023-01-29
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-01-29 deposited with the CCDC.	2024-03-11 downloaded from the CCDC.
;
_cell_angle_alpha                92.2891(15)
_cell_angle_beta                 107.0703(15)
_cell_angle_gamma                113.2351(16)
_cell_formula_units_Z            2
_cell_length_a                   8.44882(13)
_cell_length_b                   8.76255(16)
_cell_length_c                   13.5212(3)
_cell_measurement_reflns_used    9374
_cell_measurement_temperature    293
_cell_measurement_theta_max      27.59
_cell_measurement_theta_min      2.474
_cell_volume                     865.37(3)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 0.9993
_diffrn_measured_fraction_theta_max 0.9993
_diffrn_measurement_device_type
'CrysAlisPro 1.171.42.63a (Rigaku Oxford Diffraction, 2022)'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_Laue_measured_fraction_full 0.9993
_diffrn_reflns_Laue_measured_fraction_max 0.9993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            29574
_diffrn_reflns_point_group_measured_fraction_full 0.9993
_diffrn_reflns_point_group_measured_fraction_max 0.9993
_diffrn_reflns_theta_full        24.9973
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.57
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  23.3
_exptl_absorpt_correction_T_min  2.3
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            'metallic dark brown'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_description       block
_exptl_crystal_F_000             364.231
_exptl_crystal_preparation       MeOH
_exptl_crystal_recrystallization_method MeOH
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.1789
_refine_diff_density_min         -0.1442
_refine_diff_density_rms         0.0348
_refine_ls_d_res_high            0.8409
_refine_ls_d_res_low             7.9243
_refine_ls_extinction_coef       0.031(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0862
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    28
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3041
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0862
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0365
_refine_ls_shift/su_max          -0.0031
_refine_ls_shift/su_mean         0.0008
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0449P)²+0.1495P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0910
_refine_ls_wR_factor_ref         0.0995
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -10
_reflns_limit_k_max              10
_reflns_limit_k_min              -10
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                2532
_reflns_number_total             3041
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d3nj05832h2.cif
_cod_data_source_block           DSIA-H_auto
_cod_depositor_comments
'Adding full bibliography for 7063095--7063097.cif.'
_cod_original_cell_volume        865.38(3)
_cod_database_code               7063095
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C13(H13), C15(H15), C16(H16), C18(H18), C7(H7), C17(H17), C4(H4), C6(H6),
 C5(H5), C27(H27), C23(H23), C26(H26), C25(H25), C24(H24)
;
_olex2_exptl_crystal_mounting_method loop
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z
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_refinement_flags_posn
O21 O 0.82178(13) 0.53703(12) 0.91437(9) 0.0530(3) Uani 1.000000 .
N10 N 0.54945(14) 0.50217(13) 0.71873(9) 0.0362(3) Uani 1.000000 .
N2 N 0.28804(14) 0.35151(13) 0.76824(9) 0.0386(3) Uani 1.000000 .
N20 N 0.81479(15) 0.28562(14) 0.95001(10) 0.0402(3) Uani 1.000000 .
C9 C 0.47089(17) 0.59214(16) 0.66674(10) 0.0339(3) Uani 1.000000 .
C8 C 0.29120(17) 0.56808(16) 0.66081(10) 0.0351(3) Uani 1.000000 .
C14 C 0.54664(17) 0.02539(16) 0.87910(10) 0.0345(3) Uani 1.000000 .
C1 C 0.45347(16) 0.38503(15) 0.76733(10) 0.0336(3) Uani 1.000000 .
C12 C 0.54758(17) 0.28855(16) 0.82621(10) 0.0344(3) Uani 1.000000 .
C11 C 0.73627(17) 0.38174(16) 0.89794(11) 0.0379(3) Uani 1.000000 .
C22 C 0.58983(18) 0.72998(16) 0.62519(11) 0.0380(3) Uani 1.000000 .
C13 C 0.46019(17) 0.11996(16) 0.82024(10) 0.0353(3) Uani 1.000000 .
H13 H 0.33920(17) 0.06339(16) 0.77615(10) 0.0423(4) Uiso 1.000000 R
C19 C 0.72830(18) 0.11354(16) 0.94512(10) 0.0361(3) Uani 1.000000 .
C3 C 0.20586(17) 0.44625(16) 0.71595(10) 0.0368(3) Uani 1.000000 .
C15 C 0.4577(2) -0.14873(16) 0.87682(11) 0.0404(3) Uani 1.000000 .
H15 H 0.3360(2) -0.20888(16) 0.83449(11) 0.0485(4) Uiso 1.000000 R
C16 C 0.5488(2) -0.23060(18) 0.93651(11) 0.0449(4) Uani 1.000000 .
H16 H 0.4898(2) -0.34637(18) 0.93343(11) 0.0539(4) Uiso 1.000000 R
C18 C 0.81857(19) 0.02959(18) 1.00693(12) 0.0439(4) Uani 1.000000 .
H18 H 0.93879(19) 0.08896(18) 1.05160(12) 0.0527(4) Uiso 1.000000 R
C7 C 0.20270(19) 0.66682(18) 0.61264(11) 0.0444(4) Uani 1.000000 .
H7 H 0.25629(19) 0.74612(18) 0.57486(11) 0.0533(4) Uiso 1.000000 R
C17 C 0.7293(2) -0.14098(18) 1.00160(12) 0.0475(4) Uani 1.000000 .
H17 H 0.7903(2) -0.19734(18) 1.04202(12) 0.0570(5) Uiso 1.000000 R
C4 C 0.03671(19) 0.42896(19) 0.72387(12) 0.0481(4) Uani 1.000000 .
H4 H -0.02058(19) 0.34911(19) 0.76019(12) 0.0577(5) Uiso 1.000000 R
C6 C 0.0394(2) 0.6461(2) 0.62146(12) 0.0506(4) Uani 1.000000 .
H6 H -0.0183(2) 0.7108(2) 0.58905(12) 0.0608(5) Uiso 1.000000 R
C5 C -0.04267(19) 0.5285(2) 0.67865(13) 0.0524(4) Uani 1.000000 .
H5 H -0.15240(19) 0.5183(2) 0.68580(13) 0.0628(5) Uiso 1.000000 R
C27 C 0.75764(19) 0.84264(18) 0.69577(13) 0.0495(4) Uani 1.000000 .
H27 H 0.79166(19) 0.82839(18) 0.76546(13) 0.0594(5) Uiso 1.000000 R
C23 C 0.5420(2) 0.7506(2) 0.52185(13) 0.0572(4) Uani 1.000000 .
H23 H 0.4298(2) 0.6762(2) 0.47354(13) 0.0687(5) Uiso 1.000000 R
C26 C 0.8744(2) 0.9751(2) 0.66406(16) 0.0631(5) Uani 1.000000 .
H26 H 0.9858(2) 1.0510(2) 0.71236(16) 0.0757(6) Uiso 1.000000 R
C25 C 0.8264(3) 0.9951(2) 0.56131(18) 0.0704(5) Uani 1.000000 .
H25 H 0.9053(3) 1.0846(2) 0.53970(18) 0.0844(6) Uiso 1.000000 R
C24 C 0.6623(3) 0.8833(2) 0.49012(15) 0.0735(6) Uani 1.000000 .
H24 H 0.6311(3) 0.8964(2) 0.42009(15) 0.0882(7) Uiso 1.000000 R
H20 H 0.932(2) 0.342(2) 0.9953(13) 0.054(4) Uiso 1.000000 .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
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
C1 N10 C9 117.84(11) . . ?
C3 N2 C1 116.29(11) . . ?
C19 N20 C11 125.55(12) . . ?
H20 N20 C11 116.2(10) . . ?
H20 N20 C19 118.1(9) . . ?
C8 C9 N10 121.52(12) . . ?
C22 C9 N10 115.14(11) . . ?
C22 C9 C8 123.05(11) . . ?
C3 C8 C9 115.94(11) . . ?
C7 C8 C9 124.80(12) . . ?
C7 C8 C3 118.99(12) . . ?
C19 C14 C13 117.60(11) . . ?
C15 C14 C13 123.73(12) . . ?
C15 C14 C19 118.63(12) . . ?
N2 C1 N10 126.49(12) . . ?
C12 C1 N10 116.16(11) . . ?
C12 C1 N2 117.34(11) . . ?
C11 C12 C1 118.39(11) . . ?
C13 C12 C1 121.63(11) . . ?
C13 C12 C11 119.84(12) . . ?
N20 C11 O21 120.27(12) . . ?
C12 C11 O21 124.24(12) . . ?
C12 C11 N20 115.47(11) . . ?
C27 C22 C9 117.20(12) . . ?
C23 C22 C9 123.68(13) . . ?
C23 C22 C27 119.12(13) . . ?
C12 C13 C14 122.52(12) . . ?
H13 C13 C14 118.74(7) . . ?
H13 C13 C12 118.74(7) . . ?
C14 C19 N20 118.89(12) . . ?
C18 C19 N20 120.67(12) . . ?
C18 C19 C14 120.42(12) . . ?
C8 C3 N2 121.87(11) . . ?
C4 C3 N2 118.80(12) . . ?
C4 C3 C8 119.18(12) . . ?
H15 C15 C14 119.77(8) . . ?
C16 C15 C14 120.45(13) . . ?
C16 C15 H15 119.77(8) . . ?
H16 C16 C15 119.95(8) . . ?
C17 C16 C15 120.10(13) . . ?
C17 C16 H16 119.95(8) . . ?
H18 C18 C19 120.18(8) . . ?
C17 C18 C19 119.65(13) . . ?
C17 C18 H18 120.18(8) . . ?
H7 C7 C8 119.91(8) . . ?
C6 C7 C8 120.17(14) . . ?
C6 C7 H7 119.91(9) . . ?
C18 C17 C16 120.73(13) . . ?
H17 C17 C16 119.64(8) . . ?
H17 C17 C18 119.64(8) . . ?
H4 C4 C3 119.84(8) . . ?
C5 C4 C3 120.32(14) . . ?
C5 C4 H4 119.84(9) . . ?
H6 C6 C7 119.60(9) . . ?
C5 C6 C7 120.81(13) . . ?
C5 C6 H6 119.60(8) . . ?
C6 C5 C4 120.48(14) . . ?
H5 C5 C4 119.76(9) . . ?
H5 C5 C6 119.76(8) . . ?
H27 C27 C22 119.58(8) . . ?
C26 C27 C22 120.84(15) . . ?
C26 C27 H27 119.58(10) . . ?
H23 C23 C22 120.18(9) . . ?
C24 C23 C22 119.63(16) . . ?
C24 C23 H23 120.18(11) . . ?
H26 C26 C27 120.09(10) . . ?
C25 C26 C27 119.82(17) . . ?
C25 C26 H26 120.09(11) . . ?
H25 C25 C26 119.95(11) . . ?
C24 C25 C26 120.10(16) . . ?
C24 C25 H25 119.95(10) . . ?
C25 C24 C23 120.46(17) . . ?
H24 C24 C23 119.77(11) . . ?
H24 C24 C25 119.77(10) . . ?
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
O21 C11 1.2365(15) . ?
N10 C9 1.3189(16) . ?
N10 C1 1.3613(16) . ?
N2 C1 1.3140(16) . ?
N2 C3 1.3727(16) . ?
N20 C11 1.3635(16) . ?
N20 C19 1.3807(17) . ?
N20 H20 0.914(17) . ?
C9 C8 1.4249(18) . ?
C9 C22 1.4874(17) . ?
C8 C3 1.4097(18) . ?
C8 C7 1.4147(18) . ?
C14 C13 1.4291(17) . ?
C14 C19 1.3980(18) . ?
C14 C15 1.4041(18) . ?
C1 C12 1.4810(17) . ?
C12 C11 1.4665(17) . ?
C12 C13 1.3524(17) . ?
C22 C27 1.3861(19) . ?
C22 C23 1.377(2) . ?
C13 H13 0.9300 . ?
C19 C18 1.3924(18) . ?
C3 C4 1.4133(19) . ?
C15 H15 0.9300 . ?
C15 C16 1.3699(19) . ?
C16 H16 0.9300 . ?
C16 C17 1.389(2) . ?
C18 H18 0.9300 . ?
C18 C17 1.370(2) . ?
C7 H7 0.9300 . ?
C7 C6 1.360(2) . ?
C17 H17 0.9300 . ?
C4 H4 0.9300 . ?
C4 C5 1.359(2) . ?
C6 H6 0.9300 . ?
C6 C5 1.398(2) . ?
C5 H5 0.9300 . ?
C27 H27 0.9300 . ?
C27 C26 1.375(2) . ?
C23 H23 0.9300 . ?
C23 C24 1.390(2) . ?
C26 H26 0.9300 . ?
C26 C25 1.367(3) . ?
C25 H25 0.9300 . ?
C25 C24 1.371(3) . ?
C24 H24 0.9300 . ?
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
O21 C11 N20 C19 174.17(13) . . . . ?
O21 C11 C12 C1 1.52(17) . . . . ?
O21 C11 C12 C13 -174.32(14) . . . . ?
N10 C9 C8 C3 1.62(14) . . . . ?
N10 C9 C8 C7 175.61(12) . . . . ?
N10 C9 C22 C27 -52.55(13) . . . . ?
N10 C9 C22 C23 127.47(13) . . . . ?
N10 C1 N2 C3 -0.93(16) . . . . ?
N10 C1 C12 C11 47.56(13) . . . . ?
N10 C1 C12 C13 -136.68(12) . . . . ?
N2 C1 C12 C11 -131.47(12) . . . . ?
N2 C1 C12 C13 44.29(14) . . . . ?
N2 C3 C8 C9 -2.77(14) . . . . ?
N2 C3 C8 C7 -177.13(13) . . . . ?
N2 C3 C4 C5 175.81(13) . . . . ?
N20 C11 C12 C1 179.76(11) . . . . ?
N20 C11 C12 C13 3.92(14) . . . . ?
N20 C19 C14 C13 -0.23(14) . . . . ?
N20 C19 C14 C15 -178.12(12) . . . . ?
N20 C19 C18 C17 179.30(13) . . . . ?
C9 C8 C3 C4 172.78(12) . . . . ?
C9 C8 C7 C6 -172.56(14) . . . . ?
C9 C22 C27 C26 -178.97(14) . . . . ?
C9 C22 C23 C24 -179.94(16) . . . . ?
C8 C3 C4 C5 0.12(15) . . . . ?
C8 C7 C6 C5 0.53(16) . . . . ?
C14 C13 C12 C1 -177.86(12) . . . . ?
C14 C13 C12 C11 -2.17(15) . . . . ?
C14 C19 C18 C17 1.03(15) . . . . ?
C14 C15 C16 C17 1.38(16) . . . . ?
C22 C27 C26 C25 -1.09(18) . . . . ?
C22 C23 C24 C25 -1.1(2) . . . . ?
C19 C18 C17 C16 -1.06(16) . . . . ?
C3 C4 C5 C6 1.68(17) . . . . ?
C15 C16 C17 C18 -0.14(16) . . . . ?
C7 C6 C5 C4 -2.03(18) . . . . ?
C27 C26 C25 C24 0.1(2) . . . . ?
C23 C24 C25 C26 1.0(2) . . . . ?
