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#$Date: 2025-10-01 04:13:20 +0300 (Wed, 01 Oct 2025) $
#$Revision: 302324 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/25/09/7250925.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_7250925
loop_
_publ_author_name
'Santra, Souvik'
'Mondal, Rintu'
'Guchhait, Nikhil'
_publ_section_title
;
 Proton transfer across four-member hydrogen bonded network prefers over
 six-member hydrogen bonded network: Lactim-Lactam vs Imine-Amine
 photoisomerization
;
_journal_name_full               'Physical Chemistry Chemical Physics'
_journal_paper_doi               10.1039/D5CP02420J
_journal_year                    2025
_chemical_formula_moiety         'C12 H9 N3 O'
_chemical_formula_sum            'C12 H9 N3 O'
_chemical_formula_weight         211.225
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_Int_Tables_number      14
_audit_creation_date             2024-02-24
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2025-04-11 deposited with the CCDC.	2025-09-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.521(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.478(3)
_cell_length_b                   6.1791(18)
_cell_length_c                   13.853(3)
_cell_measurement_reflns_used    4406
_cell_measurement_temperature    160(2)
_cell_measurement_theta_max      33.60
_cell_measurement_theta_min      3.67
_cell_volume                     979.4(4)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      159.95
_diffrn_measured_fraction_theta_full 0.9938
_diffrn_measured_fraction_theta_max 0.8688
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0964
_diffrn_reflns_av_unetI/netI     0.0987
_diffrn_reflns_Laue_measured_fraction_full 0.9938
_diffrn_reflns_Laue_measured_fraction_max 0.8688
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12561
_diffrn_reflns_point_group_measured_fraction_full 0.9938
_diffrn_reflns_point_group_measured_fraction_max 0.8688
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         34.47
_diffrn_reflns_theta_min         3.21
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.7468
_exptl_absorpt_correction_T_min  0.3749
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1674 before and 0.1211 after correction.
The Ratio of minimum to maximum transmission is 0.5020.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            transparent
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_description       rod
_exptl_crystal_F_000             440.290
_refine_diff_density_max         0.5133
_refine_diff_density_min         -0.5337
_refine_diff_density_rms         0.1379
_refine_ls_d_res_high            0.6279
_refine_ls_d_res_low             6.3510
_refine_ls_goodness_of_fit_ref   1.1664
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    14
_refine_ls_number_parameters     153
_refine_ls_number_reflns         3588
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.1664
_refine_ls_R_factor_all          0.1295
_refine_ls_R_factor_gt           0.0843
_refine_ls_shift/su_max          -0.0008
_refine_ls_shift/su_mean         0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1613P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2222
_refine_ls_wR_factor_ref         0.2976
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              16
_reflns_limit_h_min              -19
_reflns_limit_k_max              8
_reflns_limit_k_min              0
_reflns_limit_l_max              20
_reflns_limit_l_min              0
_reflns_number_gt                2238
_reflns_number_total             3588
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d5cp02420j2.cif
_cod_data_source_block           SSS16_a
_cod_original_cell_volume        979.3(5)
_cod_database_code               7250925
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C11(H11), C10(H10), C2(H2a), C3(H3a), C5(H5), C4(H4)
;
_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+1/2,-z+1/2
3 -x,-y,-z
4 x,-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_refinement_flags_posn
O1 O 0.45309(11) 0.2520(2) 0.44464(12) 0.0393(4) Uani 1.000000 .
N2 N 0.34667(14) 0.5766(3) 0.31218(13) 0.0306(4) Uani 1.000000 .
N3 N 0.34348(14) -0.0132(3) 0.47401(13) 0.0308(4) Uani 1.000000 .
N1 N 0.15060(14) 0.5681(3) 0.23227(13) 0.0298(4) Uani 1.000000 .
C1 C 0.19258(16) 0.7466(3) 0.19739(14) 0.0282(4) Uani 1.000000 .
C8 C 0.24397(15) 0.2752(3) 0.35885(14) 0.0265(4) Uani 1.000000 .
C9 C 0.14016(15) 0.1781(3) 0.34677(14) 0.0294(4) Uani 1.000000 .
H9 H 0.06867(15) 0.2427(3) 0.30139(14) 0.0352(5) Uiso 1.000000 R
C6 C 0.31579(16) 0.7545(3) 0.24653(14) 0.0293(4) Uani 1.000000 .
C12 C 0.35311(15) 0.1768(3) 0.42666(14) 0.0284(4) Uani 1.000000 .
C7 C 0.24502(15) 0.4721(3) 0.30076(14) 0.0270(4) Uani 1.000000 .
C11 C 0.24027(17) -0.1086(3) 0.46235(15) 0.0315(4) Uani 1.000000 .
H11 H 0.24039(17) -0.2404(3) 0.49772(15) 0.0378(5) Uiso 1.000000 R
C10 C 0.13720(17) -0.0142(3) 0.39989(15) 0.0324(4) Uani 1.000000 .
H10 H 0.06480(17) -0.0771(3) 0.39235(15) 0.0389(5) Uiso 1.000000 R
C2 C 0.13183(19) 0.9095(3) 0.12664(15) 0.0346(5) Uani 1.000000 .
H2a H 0.04894(19) 0.9071(3) 0.09298(15) 0.0416(6) Uiso 1.000000 R
C3 C 0.1953(2) 1.0738(3) 0.10691(15) 0.0375(5) Uani 1.000000 .
H3a H 0.1552(2) 1.1868(3) 0.05984(15) 0.0451(6) Uiso 1.000000 R
C5 C 0.37980(19) 0.9185(3) 0.22540(16) 0.0375(5) Uani 1.000000 .
H5 H 0.46275(19) 0.9212(3) 0.25806(16) 0.0450(6) Uiso 1.000000 R
C4 C 0.3178(2) 1.0773(3) 0.15503(16) 0.0389(5) Uani 1.000000 .
H4 H 0.3591(2) 1.1912(3) 0.13887(16) 0.0467(6) Uiso 1.000000 R
H3 H 0.416(2) -0.084(4) 0.508(2) 0.051(7) Uiso 1.000000 .
H2 H 0.416(2) 0.537(4) 0.361(2) 0.048(7) 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 0.00313 0.00162 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)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
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)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
N 0.00612 0.00332 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)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
O 0.01085 0.00610 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)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
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
C7 N2 C6 107.23(15) . . ?
H2 N2 C6 130.5(17) . . ?
H2 N2 C7 121.8(17) . . ?
C11 N3 C12 124.77(16) . . ?
H3 N3 C12 112.6(16) . . ?
H3 N3 C11 122.1(16) . . ?
C7 N1 C1 104.74(15) . . ?
C6 C1 N1 110.41(15) . . ?
C2 C1 N1 129.92(18) . . ?
C2 C1 C6 119.65(18) . . ?
C12 C8 C9 119.55(17) . . ?
C7 C8 C9 120.72(16) . . ?
C7 C8 C12 119.68(15) . . ?
H9 C9 C8 119.16(11) . . ?
C10 C9 C8 121.67(17) . . ?
C10 C9 H9 119.16(10) . . ?
C1 C6 N2 104.74(16) . . ?
C5 C6 N2 133.31(18) . . ?
C5 C6 C1 121.95(17) . . ?
N3 C12 O1 119.30(15) . . ?
C8 C12 O1 125.16(17) . . ?
C8 C12 N3 115.54(15) . . ?
N1 C7 N2 112.87(17) . . ?
C8 C7 N2 122.57(15) . . ?
C8 C7 N1 124.56(16) . . ?
H11 C11 N3 120.09(11) . . ?
C10 C11 N3 119.82(18) . . ?
C10 C11 H11 120.09(12) . . ?
C11 C10 C9 118.62(18) . . ?
H10 C10 C9 120.69(10) . . ?
H10 C10 C11 120.69(12) . . ?
H2a C2 C1 120.82(12) . . ?
C3 C2 C1 118.4(2) . . ?
C3 C2 H2a 120.82(13) . . ?
H3a C3 C2 119.35(13) . . ?
C4 C3 C2 121.30(19) . . ?
C4 C3 H3a 119.35(12) . . ?
H5 C5 C6 121.34(12) . . ?
C4 C5 C6 117.3(2) . . ?
C4 C5 H5 121.34(13) . . ?
C5 C4 C3 121.39(19) . . ?
H4 C4 C3 119.30(12) . . ?
H4 C4 C5 119.30(13) . . ?
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 C12 1.259(2) . ?
N2 C6 1.380(2) . ?
N2 C7 1.375(2) . ?
N2 H2 0.90(3) . ?
N3 C12 1.374(2) . ?
N3 C11 1.366(3) . ?
N3 H3 0.95(3) . ?
N1 C1 1.388(2) . ?
N1 C7 1.322(2) . ?
C1 C6 1.412(3) . ?
C1 C2 1.398(3) . ?
C8 C9 1.376(3) . ?
C8 C12 1.444(2) . ?
C8 C7 1.461(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.406(3) . ?
C6 C5 1.392(3) . ?
C11 H11 0.9500 . ?
C11 C10 1.362(3) . ?
C10 H10 0.9500 . ?
C2 H2a 0.9500 . ?
C2 C3 1.380(3) . ?
C3 H3a 0.9500 . ?
C3 C4 1.404(3) . ?
C5 H5 0.9500 . ?
C5 C4 1.382(3) . ?
C4 H4 0.9500 . ?
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
O1 C12 N3 C11 178.70(19) . . . . ?
O1 C12 C8 C9 -179.1(2) . . . . ?
O1 C12 C8 C7 3.2(2) . . . . ?
N2 C6 C1 N1 -0.29(17) . . . . ?
N2 C6 C1 C2 178.41(14) . . . . ?
N2 C6 C5 C4 -178.4(2) . . . . ?
N2 C7 N1 C1 -0.48(17) . . . . ?
N2 C7 C8 C9 178.62(19) . . . . ?
N2 C7 C8 C12 -3.7(2) . . . . ?
N3 C12 C8 C9 0.7(2) . . . . ?
N3 C12 C8 C7 -176.96(16) . . . . ?
N3 C11 C10 C9 1.4(2) . . . . ?
N1 C1 C6 C5 -179.84(16) . . . . ?
N1 C1 C2 C3 178.6(2) . . . . ?
N1 C7 C8 C9 -1.6(2) . . . . ?
N1 C7 C8 C12 175.99(19) . . . . ?
C1 C6 C5 C4 1.0(2) . . . . ?
C1 C2 C3 C4 0.9(2) . . . . ?
C8 C9 C10 C11 -1.9(2) . . . . ?
C6 C5 C4 C3 0.2(2) . . . . ?
C2 C3 C4 C5 -1.1(3) . . . . ?
