#------------------------------------------------------------------------------
#$Date: 2025-08-23 00:35:05 +0200 (Sat 23 de Aug de 2025) $
#$Revision: 301870 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/01/7240100.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_7240100
loop_
_publ_author_name
'Barboza, Cristina A.'
'Gawrys, Pawel'
'Banasiewicz, Marzena'
'Suwinska, Kinga'
'Sobolewski, Andrzej L.'
_publ_section_title
;
 Photophysical transformations induced by chemical substitution to
 salicylaldimines.
;
_journal_issue                   12
_journal_name_full               'Physical chemistry chemical physics : PCCP'
_journal_page_first              6698
_journal_page_last               6705
_journal_paper_doi               10.1039/d0cp00110d
_journal_volume                  22
_journal_year                    2020
_chemical_formula_moiety         'C19 H18 N4 O'
_chemical_formula_sum            'C19 H18 N4 O'
_chemical_formula_weight         318.37
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2019-05-27 deposited with the CCDC.	2020-03-08 downloaded from the CCDC.
;
_cell_angle_alpha                112.92(9)
_cell_angle_beta                 96.63(8)
_cell_angle_gamma                92.67(11)
_cell_formula_units_Z            2
_cell_length_a                   4.875(4)
_cell_length_b                   13.717(17)
_cell_length_c                   14.116(11)
_cell_measurement_reflns_used    4768
_cell_measurement_temperature    274(2)
_cell_measurement_theta_max      54.5823
_cell_measurement_theta_min      3.430
_cell_volume                     859.3(16)
_computing_cell_refinement       'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_data_collection       'Bruker Instrument Service v4.2.9'
_computing_data_reduction        'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      274(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'D8 VENTURE DUO'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0832
_diffrn_reflns_av_unetI/netI     0.0481
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            21603
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        59.215
_diffrn_reflns_theta_max         59.215
_diffrn_reflns_theta_min         3.436
_diffrn_source                   I\mS
_exptl_absorpt_coefficient_mu    0.632
_exptl_absorpt_correction_T_max  0.7516
_exptl_absorpt_correction_T_min  0.6900
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            yellow-orange
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_description       needle
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.254
_exptl_crystal_size_mid          0.076
_exptl_crystal_size_min          0.044
_refine_diff_density_max         0.106
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         2465
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.1238
_refine_ls_R_factor_gt           0.0608
_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)+(0.0513P)²+0.2256P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1150
_refine_ls_wR_factor_ref         0.1383
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1362
_reflns_number_total             2465
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cp00110d2.cif
_cod_data_source_block           cu_PGIG186
_cod_depositor_comments
'Adding full bibliography for 7240097--7240102.cif.'
_cod_original_cell_volume        859.1(16)
_cod_database_code               7240100
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-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_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 0.5420(5) 0.36709(18) 0.91835(16) 0.0809(7) Uani 1 1 d . . . . .
H1O H 0.418669 0.399128 0.902788 0.121 Uiso 1 1 calc R U . . .
N1 N 0.2358(5) 0.43574(19) 0.80056(19) 0.0593(7) Uani 1 1 d . . . . .
N2 N 1.0524(6) 0.0746(2) 0.7614(2) 0.0911(9) Uani 1 1 d . . . . .
N3 N -0.6416(7) 0.7961(3) 0.7798(3) 0.1192(13) Uani 1 1 d . . . . .
N4 N -0.3092(8) 0.6251(3) 0.5264(3) 0.1229(13) Uani 1 1 d . . . . .
C1 C 0.3288(6) 0.3665(2) 0.7224(2) 0.0612(8) Uani 1 1 d . . . . .
H1 H 0.265917 0.362198 0.655980 0.073 Uiso 1 1 calc R U . . .
C2 C 0.5230(6) 0.2967(2) 0.7338(2) 0.0544(8) Uani 1 1 d . . . . .
C3 C 0.6221(6) 0.2967(2) 0.8308(2) 0.0582(8) Uani 1 1 d . . . . .
C4 C 0.8012(6) 0.2259(2) 0.8404(3) 0.0695(9) Uani 1 1 d . . . . .
H4 H 0.866223 0.228768 0.906166 0.083 Uiso 1 1 calc R U . . .
C5 C 0.8876(6) 0.1493(2) 0.7531(3) 0.0652(9) Uani 1 1 d . . . . .
C6 C 0.7962(6) 0.1503(2) 0.6554(2) 0.0719(9) Uani 1 1 d . . . . .
H6 H 0.855340 0.102033 0.596103 0.086 Uiso 1 1 calc R U . . .
C7 C 0.6209(6) 0.2222(2) 0.6478(2) 0.0696(9) Uani 1 1 d . . . . .
H7 H 0.563653 0.221725 0.582419 0.084 Uiso 1 1 calc R U . . .
C8A C 1.218(3) 0.0901(8) 0.8613(11) 0.091(5) Uani 0.60(3) 1 d . . P A -1
H8AA H 1.262107 0.165378 0.904098 0.109 Uiso 0.60(3) 1 calc R U P A -1
H8AB H 1.389933 0.057476 0.849631 0.109 Uiso 0.60(3) 1 calc R U P A -1
C9A C 1.049(4) 0.0396(11) 0.9133(16) 0.148(6) Uani 0.60(3) 1 d . . P A -1
H9AA H 0.977804 -0.031152 0.865431 0.222 Uiso 0.60(3) 1 calc R U P A -1
H9AB H 0.896654 0.080637 0.935995 0.222 Uiso 0.60(3) 1 calc R U P A -1
H9AC H 1.161475 0.036477 0.972276 0.222 Uiso 0.60(3) 1 calc R U P A -1
C8B C 1.036(4) 0.0391(12) 0.8562(14) 0.062(5) Uani 0.40(3) 1 d . . P A -2
H8BA H 0.877088 0.065821 0.890581 0.074 Uiso 0.40(3) 1 calc R U P A -2
H8BB H 1.017373 -0.037834 0.831515 0.074 Uiso 0.40(3) 1 calc R U P A -2
C9B C 1.300(5) 0.0856(11) 0.930(2) 0.110(7) Uani 0.40(3) 1 d . . P A -2
H9BA H 1.449709 0.046267 0.900966 0.132 Uiso 0.40(3) 1 calc R U P A -2
H9BB H 1.281674 0.081586 0.995083 0.132 Uiso 0.40(3) 1 calc R U P A -2
H9BC H 1.338271 0.158570 0.940006 0.132 Uiso 0.40(3) 1 calc R U P A -2
C10 C 1.1456(8) -0.0074(3) 0.6710(3) 0.0954(12) Uani 1 1 d . . . . .
H10A H 1.313507 -0.032084 0.694003 0.114 Uiso 1 1 calc R U . . .
H10B H 1.190388 0.024026 0.623136 0.114 Uiso 1 1 calc R U . . .
C11 C 0.9350(9) -0.0990(3) 0.6159(3) 0.1250(15) Uani 1 1 d . . . . .
H11A H 0.775639 -0.076355 0.586343 0.187 Uiso 1 1 calc R U . . .
H11B H 0.880844 -0.127581 0.663874 0.187 Uiso 1 1 calc R U . . .
H11C H 1.011202 -0.152709 0.561443 0.187 Uiso 1 1 calc R U . . .
C12 C 0.0479(6) 0.5053(2) 0.7877(2) 0.0545(7) Uani 1 1 d . . . . .
C13 C -0.0727(6) 0.5636(2) 0.8741(2) 0.0657(9) Uani 1 1 d . . . . .
H13 H -0.029355 0.553252 0.935234 0.079 Uiso 1 1 calc R U . . .
C14 C -0.2537(6) 0.6360(2) 0.8716(2) 0.0710(9) Uani 1 1 d . . . . .
H14 H -0.334016 0.673288 0.930283 0.085 Uiso 1 1 calc R U . . .
C15 C -0.3180(6) 0.6541(2) 0.7821(3) 0.0619(8) Uani 1 1 d . . . . .
C16 C -0.1986(6) 0.5956(2) 0.6949(2) 0.0609(8) Uani 1 1 d . . . . .
C17 C -0.0195(6) 0.5219(2) 0.6977(2) 0.0632(8) Uani 1 1 d . . . . .
H17 H 0.056909 0.482905 0.638503 0.076 Uiso 1 1 calc R U . . .
C18 C -0.4976(7) 0.7336(3) 0.7809(3) 0.0803(10) Uani 1 1 d . . . . .
C19 C -0.2622(7) 0.6118(3) 0.6004(3) 0.0824(11) 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C3 O1 H1O 109.5 . . ?
C1 N1 C12 121.6(3) . . ?
C5 N2 C10 122.7(3) . . ?
C5 N2 C8A 121.1(4) . . ?
C10 N2 C8A 113.6(4) . . ?
C5 N2 C8B 118.4(5) . . ?
C10 N2 C8B 113.3(5) . . ?
N1 C1 C2 122.5(3) . . ?
N1 C1 H1 118.7 . . ?
C2 C1 H1 118.7 . . ?
C3 C2 C7 116.5(3) . . ?
C3 C2 C1 122.1(3) . . ?
C7 C2 C1 121.5(3) . . ?
O1 C3 C4 118.0(3) . . ?
O1 C3 C2 120.5(3) . . ?
C4 C3 C2 121.5(3) . . ?
C3 C4 C5 121.1(3) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
N2 C5 C4 121.4(3) . . ?
N2 C5 C6 120.6(3) . . ?
C4 C5 C6 118.0(3) . . ?
C7 C6 C5 119.9(3) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C7 C2 123.0(3) . . ?
C6 C7 H7 118.5 . . ?
C2 C7 H7 118.5 . . ?
N2 C8A C9A 107.2(15) . . ?
N2 C8A H8AA 110.3 . . ?
C9A C8A H8AA 110.3 . . ?
N2 C8A H8AB 110.3 . . ?
C9A C8A H8AB 110.3 . . ?
H8AA C8A H8AB 108.5 . . ?
C8A C9A H9AA 109.5 . . ?
C8A C9A H9AB 109.5 . . ?
H9AA C9A H9AB 109.5 . . ?
C8A C9A H9AC 109.5 . . ?
H9AA C9A H9AC 109.5 . . ?
H9AB C9A H9AC 109.5 . . ?
C9B C8B N2 106.4(18) . . ?
C9B C8B H8BA 110.4 . . ?
N2 C8B H8BA 110.4 . . ?
C9B C8B H8BB 110.4 . . ?
N2 C8B H8BB 110.4 . . ?
H8BA C8B H8BB 108.6 . . ?
C8B C9B H9BA 109.5 . . ?
C8B C9B H9BB 109.5 . . ?
H9BA C9B H9BB 109.5 . . ?
C8B C9B H9BC 109.5 . . ?
H9BA C9B H9BC 109.5 . . ?
H9BB C9B H9BC 109.5 . . ?
N2 C10 C11 112.7(3) . . ?
N2 C10 H10A 109.1 . . ?
C11 C10 H10A 109.1 . . ?
N2 C10 H10B 109.1 . . ?
C11 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C17 C12 C13 118.3(3) . . ?
C17 C12 N1 125.4(3) . . ?
C13 C12 N1 116.3(3) . . ?
C14 C13 C12 121.5(3) . . ?
C14 C13 H13 119.2 . . ?
C12 C13 H13 119.2 . . ?
C13 C14 C15 120.3(3) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C14 C15 C16 118.5(3) . . ?
C14 C15 C18 120.3(3) . . ?
C16 C15 C18 121.2(3) . . ?
C17 C16 C15 120.8(3) . . ?
C17 C16 C19 119.2(3) . . ?
C15 C16 C19 120.1(3) . . ?
C16 C17 C12 120.6(3) . . ?
C16 C17 H17 119.7 . . ?
C12 C17 H17 119.7 . . ?
N3 C18 C15 179.5(4) . . ?
N4 C19 C16 179.2(4) . . ?
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 C3 1.352(4) . ?
O1 H1O 0.8200 . ?
N1 C1 1.290(4) . ?
N1 C12 1.400(4) . ?
N2 C5 1.363(4) . ?
N2 C10 1.471(4) . ?
N2 C8A 1.474(16) . ?
N2 C8B 1.601(17) . ?
N3 C18 1.138(4) . ?
N4 C19 1.129(4) . ?
C1 C2 1.417(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.398(4) . ?
C2 C7 1.400(4) . ?
C3 C4 1.371(4) . ?
C4 C5 1.398(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.405(4) . ?
C6 C7 1.361(4) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8A C9A 1.48(3) . ?
C8A H8AA 0.9700 . ?
C8A H8AB 0.9700 . ?
C9A H9AA 0.9600 . ?
C9A H9AB 0.9600 . ?
C9A H9AC 0.9600 . ?
C8B C9B 1.50(4) . ?
C8B H8BA 0.9700 . ?
C8B H8BB 0.9700 . ?
C9B H9BA 0.9600 . ?
C9B H9BB 0.9600 . ?
C9B H9BC 0.9600 . ?
C10 C11 1.474(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C17 1.382(4) . ?
C12 C13 1.387(4) . ?
C13 C14 1.367(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.385(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.392(4) . ?
C15 C18 1.433(5) . ?
C16 C17 1.376(4) . ?
C16 C19 1.436(5) . ?
C17 H17 0.9300 . ?
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
O1 H1O N1 0.82 1.85 2.580(4) 146.9 . yes
C1 H1 N4 0.93 2.68 3.549(5) 156.1 2_566 yes
C17 H17 N4 0.93 2.70 3.625(6) 176.5 2_566 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
C12 N1 C1 C2 178.8(2) . . . . ?
N1 C1 C2 C3 1.5(4) . . . . ?
N1 C1 C2 C7 -180.0(3) . . . . ?
C7 C2 C3 O1 179.0(3) . . . . ?
C1 C2 C3 O1 -2.4(4) . . . . ?
C7 C2 C3 C4 -1.3(4) . . . . ?
C1 C2 C3 C4 177.3(3) . . . . ?
O1 C3 C4 C5 178.5(3) . . . . ?
C2 C3 C4 C5 -1.2(5) . . . . ?
C10 N2 C5 C4 179.7(3) . . . . ?
C8A N2 C5 C4 -19.7(8) . . . . ?
C8B N2 C5 C4 27.8(9) . . . . ?
C10 N2 C5 C6 0.6(5) . . . . ?
C8A N2 C5 C6 161.3(7) . . . . ?
C8B N2 C5 C6 -151.3(9) . . . . ?
C3 C4 C5 N2 -176.1(3) . . . . ?
C3 C4 C5 C6 3.0(5) . . . . ?
N2 C5 C6 C7 176.8(3) . . . . ?
C4 C5 C6 C7 -2.3(5) . . . . ?
C5 C6 C7 C2 -0.3(5) . . . . ?
C3 C2 C7 C6 2.1(4) . . . . ?
C1 C2 C7 C6 -176.5(3) . . . . ?
C5 N2 C8A C9A 92.8(8) . . . . ?
C10 N2 C8A C9A -104.9(7) . . . . ?
C5 N2 C8B C9B -108.2(8) . . . . ?
C10 N2 C8B C9B 97.3(8) . . . . ?
C5 N2 C10 C11 -82.0(4) . . . . ?
C8A N2 C10 C11 116.0(7) . . . . ?
C8B N2 C10 C11 71.2(9) . . . . ?
C1 N1 C12 C17 -12.2(4) . . . . ?
C1 N1 C12 C13 169.6(3) . . . . ?
C17 C12 C13 C14 0.0(4) . . . . ?
N1 C12 C13 C14 178.3(3) . . . . ?
C12 C13 C14 C15 -1.0(5) . . . . ?
C13 C14 C15 C16 1.2(5) . . . . ?
C13 C14 C15 C18 -177.1(3) . . . . ?
C14 C15 C16 C17 -0.3(4) . . . . ?
C18 C15 C16 C17 177.9(3) . . . . ?
C14 C15 C16 C19 179.5(3) . . . . ?
C18 C15 C16 C19 -2.2(5) . . . . ?
C15 C16 C17 C12 -0.7(4) . . . . ?
C19 C16 C17 C12 179.4(3) . . . . ?
C13 C12 C17 C16 0.9(4) . . . . ?
N1 C12 C17 C16 -177.2(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168341137
