# Supplementary Information (SI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2025

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3a
_database_code_depnum_ccdc_archive 'CCDC 2469646'
loop_
_audit_author_name
_audit_author_address
'Ivan A. Moskalev'
;Synchrotron Radiation Facility SKIF
Russia
;
_audit_update_record             
;
2025-07-03 deposited with the CCDC.	2025-10-20 downloaded from the CCDC.
;
_audit_creation_date             2025-07-03
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2017/1
loop_
_audit_author_email
i.a.moskalev@srf-skif.ru
_chemical_name_common            ?
_chemical_name_systematic        
3-Hydroxy-6,6-dimethyl-2-((E)-2-(4-nitrophenyl)ethenyl)-3,5,6,7-tetrahydro-4H-benzimidazol-4-one
_chemical_formula_moiety         'C17 H17 N3 O4, C3 H7 N O'
_chemical_formula_sum            'C20 H24 N4 O5'
_chemical_formula_weight         400.43
_chemical_melting_point          503-505
_chemical_oxdiff_formula         'C17 H17 N3 O4'
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.4075(5)
_cell_length_b                   13.1203(11)
_cell_length_c                   21.0062(15)
_cell_angle_alpha                90
_cell_angle_beta                 92.715(6)
_cell_angle_gamma                90
_cell_volume                     2039.3(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1488
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      32.1270
_cell_measurement_theta_min      2.7560
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.956
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63044
_exptl_absorpt_correction_type   cylinder
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.143a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plank
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.08
_exptl_crystal_size_rad          0.400
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0817
_diffrn_reflns_av_unetI/netI     0.0634
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.936
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            12599
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.574
_diffrn_reflns_theta_min         1.941
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.936
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -65.00 115.00   0.50   61.00    --   25.00   0.00  35.00  360
  2  ω    -65.00 -53.50   0.50   61.00    --   25.00   0.00 125.00   23
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'esperanto-CrysAlisPro-abstract goniometer imported esperanto images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0429673000
_diffrn_orient_matrix_UB_12      0.0102379000
_diffrn_orient_matrix_UB_13      0.0302085000
_diffrn_orient_matrix_UB_21      -0.0752701000
_diffrn_orient_matrix_UB_22      -0.0207760000
_diffrn_orient_matrix_UB_23      0.0151866000
_diffrn_orient_matrix_UB_31      0.0410639000
_diffrn_orient_matrix_UB_32      -0.0488631000
_diffrn_orient_matrix_UB_33      -0.0001334000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3387
_reflns_number_total             5367
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024) (IMPORT)'
_computing_data_reduction        'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         5367
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0888
_refine_ls_R_factor_gt           0.0592
_refine_ls_restrained_S_all      1.038
_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)+(0.0811P)²+0.0147P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1604
_refine_ls_wR_factor_ref         0.1871
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 N1, O2
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
N1 \\sim O2: within 1.7A with sigma of 0.04 and sigma for terminal atoms of
0.08 within 1.7A
4.a Secondary CH2 refined with riding coordinates:
 C13(H13a,H13b), C15(H15a,H15b)
4.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C5(H5), C6(H6), C3(H3a), C2(H2)
4.c Idealised Me refined as rotating group:
 C16(H16a,H16b,H16c), C20(H20a,H20b,H20c), C19(H19a,H19b,H19c), C17(H17a,H17b,
 H17c)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O3 O 0.57121(19) 0.15277(9) 0.46508(6) 0.0603(4) Uani 1 1 d . . . . .
N2 N 0.54915(18) 0.21903(9) 0.41455(7) 0.0481(3) Uani 1 1 d . . . . .
N3 N 0.56663(19) 0.36145(10) 0.35953(7) 0.0496(3) Uani 1 1 d . . . . .
O4 O 0.4132(2) 0.02100(9) 0.35603(7) 0.0770(5) Uani 1 1 d . . . . .
O1 O 1.0543(2) 0.76741(10) 0.68530(8) 0.0789(5) Uani 1 1 d . . . . .
O5 O 0.2555(2) 0.13928(11) 0.50841(7) 0.0769(4) Uani 1 1 d . . . . .
O2 O 1.0725(2) 0.62844(12) 0.73904(7) 0.0818(5) Uani 1 1 d . U . . .
N1 N 1.0317(2) 0.67541(12) 0.69035(7) 0.0571(4) Uani 1 1 d . U . . .
N4 N 0.0873(2) 0.06270(11) 0.58059(8) 0.0607(4) Uani 1 1 d . . . . .
C9 C 0.5988(2) 0.31797(12) 0.41657(8) 0.0459(4) Uani 1 1 d . . . . .
C4 C 0.7961(2) 0.51534(11) 0.53325(7) 0.0437(4) Uani 1 1 d . . . . .
C1 C 0.9522(2) 0.61981(12) 0.63593(8) 0.0466(4) Uani 1 1 d . . . . .
C7 C 0.7132(2) 0.46278(12) 0.47827(8) 0.0484(4) Uani 1 1 d . . . . .
H7 H 0.683382 0.502536 0.442658 0.058 Uiso 1 1 calc R U . . .
C11 C 0.4931(2) 0.28699(12) 0.32180(8) 0.0478(4) Uani 1 1 d . . . . .
C8 C 0.6762(2) 0.36485(12) 0.47369(8) 0.0485(4) Uani 1 1 d . . . . .
H8 H 0.701127 0.323778 0.509101 0.058 Uiso 1 1 calc R U . . .
C10 C 0.4817(2) 0.19712(12) 0.35436(8) 0.0478(4) Uani 1 1 d . . . . .
C5 C 0.8106(2) 0.62124(12) 0.53255(8) 0.0482(4) Uani 1 1 d . . . . .
H5 H 0.766452 0.657137 0.496946 0.058 Uiso 1 1 calc R U . . .
C6 C 0.8888(2) 0.67387(12) 0.58341(8) 0.0501(4) Uani 1 1 d . . . . .
H6 H 0.898681 0.744508 0.582274 0.060 Uiso 1 1 calc R U . . .
C12 C 0.4103(2) 0.10267(13) 0.32795(9) 0.0541(4) Uani 1 1 d . . . . .
C3 C 0.8656(2) 0.46419(12) 0.58733(8) 0.0527(4) Uani 1 1 d . . . . .
H3A H 0.860108 0.393406 0.588473 0.063 Uiso 1 1 calc R U . . .
C2 C 0.9416(2) 0.51531(13) 0.63869(8) 0.0531(4) Uani 1 1 d . . . . .
H2 H 0.985078 0.480128 0.674659 0.064 Uiso 1 1 calc R U . . .
C18 C 0.2351(3) 0.07512(14) 0.55052(9) 0.0585(5) Uani 1 1 d . . . . .
C13 C 0.3282(3) 0.11535(14) 0.26167(9) 0.0602(5) Uani 1 1 d . . . . .
H13A H 0.202303 0.134295 0.264786 0.072 Uiso 1 1 calc R U . . .
H13B H 0.330866 0.049860 0.240308 0.072 Uiso 1 1 calc R U . . .
C15 C 0.4333(3) 0.29806(13) 0.25352(8) 0.0577(5) Uani 1 1 d . . . . .
H15A H 0.518720 0.340665 0.232179 0.069 Uiso 1 1 calc R U . . .
H15B H 0.316483 0.331602 0.250544 0.069 Uiso 1 1 calc R U . . .
C14 C 0.4189(3) 0.19433(15) 0.21987(9) 0.0619(5) Uani 1 1 d . . . . .
C16 C 0.6072(3) 0.15571(19) 0.20467(12) 0.0876(7) Uani 1 1 d . . . . .
H16A H 0.680141 0.149349 0.243475 0.131 Uiso 1 1 calc R U . . .
H16B H 0.662749 0.203143 0.176829 0.131 Uiso 1 1 calc R U . . .
H16C H 0.596689 0.090427 0.184193 0.131 Uiso 1 1 calc R U . . .
C20 C 0.0720(4) -0.01608(19) 0.62870(13) 0.0997(9) Uani 1 1 d . . . . .
H20A H 0.185187 -0.051329 0.634430 0.150 Uiso 1 1 calc R U . . .
H20B H -0.020740 -0.063515 0.615173 0.150 Uiso 1 1 calc R U . . .
H20C H 0.041495 0.014571 0.668272 0.150 Uiso 1 1 calc R U . . .
C19 C -0.0700(3) 0.12546(19) 0.56728(14) 0.0947(8) Uani 1 1 d . . . . .
H19A H -0.048148 0.170207 0.532313 0.142 Uiso 1 1 calc R U . . .
H19B H -0.094339 0.165132 0.604306 0.142 Uiso 1 1 calc R U . . .
H19C H -0.172110 0.082803 0.556372 0.142 Uiso 1 1 calc R U . . .
C17 C 0.3043(4) 0.20663(19) 0.15744(11) 0.1000(9) Uani 1 1 d . . . . .
H17A H 0.290240 0.141541 0.136920 0.150 Uiso 1 1 calc R U . . .
H17B H 0.363372 0.252880 0.129777 0.150 Uiso 1 1 calc R U . . .
H17C H 0.187546 0.233157 0.166616 0.150 Uiso 1 1 calc R U . . .
H3 H 0.445(4) 0.147(2) 0.4842(14) 0.146(12) Uiso 1 1 d . . . . .
H18 H 0.334(3) 0.0291(15) 0.5645(9) 0.075(6) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
O3 N2 1.3757(17) . ?
O3 H3 1.03(3) . ?
N2 C9 1.349(2) . ?
N2 C10 1.368(2) . ?
N3 C9 1.338(2) . ?
N3 C11 1.356(2) . ?
O4 C12 1.223(2) . ?
O1 N1 1.2239(19) . ?
O5 C18 1.235(2) . ?
O2 N1 1.2199(19) . ?
N1 C1 1.457(2) . ?
N4 C18 1.300(2) . ?
N4 C20 1.454(2) . ?
N4 C19 1.443(3) . ?
C9 C8 1.443(2) . ?
C4 C7 1.456(2) . ?
C4 C5 1.394(2) . ?
C4 C3 1.397(2) . ?
C1 C6 1.375(2) . ?
C1 C2 1.375(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.316(2) . ?
C11 C10 1.368(2) . ?
C11 C15 1.488(2) . ?
C8 H8 0.9300 . ?
C10 C12 1.447(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.377(2) . ?
C6 H6 0.9300 . ?
C12 C13 1.502(2) . ?
C3 H3A 0.9300 . ?
C3 C2 1.368(2) . ?
C2 H2 0.9300 . ?
C18 H18 0.98(2) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.534(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C14 1.535(2) . ?
C14 C16 1.531(3) . ?
C14 C17 1.537(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

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
N2 O3 H3 105.6(17) . . ?
C9 N2 O3 124.16(13) . . ?
C9 N2 C10 108.56(13) . . ?
C10 N2 O3 127.24(13) . . ?
C9 N3 C11 105.41(13) . . ?
O1 N1 C1 118.55(15) . . ?
O2 N1 O1 122.77(16) . . ?
O2 N1 C1 118.68(15) . . ?
C18 N4 C20 121.46(18) . . ?
C18 N4 C19 121.68(18) . . ?
C19 N4 C20 116.8(2) . . ?
N2 C9 C8 122.23(15) . . ?
N3 C9 N2 110.20(14) . . ?
N3 C9 C8 127.56(15) . . ?
C5 C4 C7 119.58(15) . . ?
C5 C4 C3 117.53(15) . . ?
C3 C4 C7 122.89(15) . . ?
C6 C1 N1 118.76(15) . . ?
C2 C1 N1 119.22(15) . . ?
C2 C1 C6 122.02(15) . . ?
C4 C7 H7 116.6 . . ?
C8 C7 C4 126.80(16) . . ?
C8 C7 H7 116.6 . . ?
N3 C11 C10 111.19(15) . . ?
N3 C11 C15 125.89(14) . . ?
C10 C11 C15 122.91(14) . . ?
C9 C8 H8 118.3 . . ?
C7 C8 C9 123.38(16) . . ?
C7 C8 H8 118.3 . . ?
N2 C10 C12 130.16(15) . . ?
C11 C10 N2 104.62(13) . . ?
C11 C10 C12 125.21(16) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 C4 121.43(15) . . ?
C6 C5 H5 119.3 . . ?
C1 C6 C5 118.61(15) . . ?
C1 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
O4 C12 C10 124.59(17) . . ?
O4 C12 C13 122.76(16) . . ?
C10 C12 C13 112.65(15) . . ?
C4 C3 H3A 119.1 . . ?
C2 C3 C4 121.85(15) . . ?
C2 C3 H3A 119.1 . . ?
C1 C2 H2 120.7 . . ?
C3 C2 C1 118.54(15) . . ?
C3 C2 H2 120.7 . . ?
O5 C18 N4 124.56(19) . . ?
O5 C18 H18 121.3(12) . . ?
N4 C18 H18 114.2(12) . . ?
C12 C13 H13A 108.3 . . ?
C12 C13 H13B 108.3 . . ?
C12 C13 C14 115.85(15) . . ?
H13A C13 H13B 107.4 . . ?
C14 C13 H13A 108.3 . . ?
C14 C13 H13B 108.3 . . ?
C11 C15 H15A 109.3 . . ?
C11 C15 H15B 109.3 . . ?
C11 C15 C14 111.61(14) . . ?
H15A C15 H15B 108.0 . . ?
C14 C15 H15A 109.3 . . ?
C14 C15 H15B 109.3 . . ?
C13 C14 C15 110.97(16) . . ?
C13 C14 C17 108.65(17) . . ?
C15 C14 C17 108.86(16) . . ?
C16 C14 C13 108.90(17) . . ?
C16 C14 C15 110.21(16) . . ?
C16 C14 C17 109.2(2) . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N4 C20 H20A 109.5 . . ?
N4 C20 H20B 109.5 . . ?
N4 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N4 C19 H19A 109.5 . . ?
N4 C19 H19B 109.5 . . ?
N4 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

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
O3 N2 C9 N3 177.57(15) . . . . ?
O3 N2 C9 C8 -1.9(2) . . . . ?
O3 N2 C10 C11 -178.07(15) . . . . ?
O3 N2 C10 C12 2.6(3) . . . . ?
N2 C9 C8 C7 -174.79(16) . . . . ?
N2 C10 C12 O4 -6.5(3) . . . . ?
N2 C10 C12 C13 172.59(17) . . . . ?
N3 C9 C8 C7 5.8(3) . . . . ?
N3 C11 C10 N2 0.80(19) . . . . ?
N3 C11 C10 C12 -179.78(16) . . . . ?
N3 C11 C15 C14 160.35(17) . . . . ?
O4 C12 C13 C14 -146.91(19) . . . . ?
O1 N1 C1 C6 -6.5(2) . . . . ?
O1 N1 C1 C2 173.89(17) . . . . ?
O2 N1 C1 C6 173.32(17) . . . . ?
O2 N1 C1 C2 -6.3(3) . . . . ?
N1 C1 C6 C5 -178.77(15) . . . . ?
N1 C1 C2 C3 179.65(16) . . . . ?
C9 N2 C10 C11 -0.32(18) . . . . ?
C9 N2 C10 C12 -179.70(17) . . . . ?
C9 N3 C11 C10 -0.96(19) . . . . ?
C9 N3 C11 C15 179.79(17) . . . . ?
C4 C7 C8 C9 -177.98(15) . . . . ?
C4 C5 C6 C1 -0.5(3) . . . . ?
C4 C3 C2 C1 -1.3(3) . . . . ?
C7 C4 C5 C6 -179.67(15) . . . . ?
C7 C4 C3 C2 -179.44(16) . . . . ?
C11 N3 C9 N2 0.73(18) . . . . ?
C11 N3 C9 C8 -179.81(16) . . . . ?
C11 C10 C12 O4 174.22(19) . . . . ?
C11 C10 C12 C13 -6.7(3) . . . . ?
C11 C15 C14 C13 43.4(2) . . . . ?
C11 C15 C14 C16 -77.3(2) . . . . ?
C11 C15 C14 C17 162.93(19) . . . . ?
C10 N2 C9 N3 -0.26(18) . . . . ?
C10 N2 C9 C8 -179.75(14) . . . . ?
C10 C11 C15 C14 -18.8(3) . . . . ?
C10 C12 C13 C14 34.0(2) . . . . ?
C5 C4 C7 C8 -173.90(17) . . . . ?
C5 C4 C3 C2 1.5(3) . . . . ?
C6 C1 C2 C3 0.1(3) . . . . ?
C12 C13 C14 C15 -53.4(2) . . . . ?
C12 C13 C14 C16 68.1(2) . . . . ?
C12 C13 C14 C17 -173.06(17) . . . . ?
C3 C4 C7 C8 7.1(3) . . . . ?
C3 C4 C5 C6 -0.6(2) . . . . ?
C2 C1 C6 C5 0.8(3) . . . . ?
C15 C11 C10 N2 -179.92(16) . . . . ?
C15 C11 C10 C12 -0.5(3) . . . . ?
C20 N4 C18 O5 178.6(2) . . . . ?
C19 N4 C18 O5 -0.6(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.758
_oxdiff_exptl_absorpt_empirical_full_min 0.574
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DMF'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_6d
_database_code_depnum_ccdc_archive 'CCDC 2469650'
loop_
_audit_author_name
_audit_author_address
'Ivan A. Moskalev'
;Synchrotron Radiation Facility SKIF
Russia
;
_audit_update_record             
;
2025-07-03 deposited with the CCDC.	2025-10-20 downloaded from the CCDC.
;
_audit_creation_date             2025-05-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2017/1
loop_
_audit_author_email
i.a.moskalev@srf-skif.ru
_chemical_name_common            ?
_chemical_name_systematic        
1,4,5-Trimethyl-2-((E)-2-phenylethenyl)-1H-imidazole
_chemical_formula_moiety         'C14 H16 N2 O, H2 O'
_chemical_formula_sum            'C14 H18 N2 O2'
_chemical_formula_weight         246.30
_chemical_melting_point          445-447
_chemical_oxdiff_formula         'C14 H18 N2 O2'
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   13.398(2)
_cell_length_b                   9.5481(13)
_cell_length_c                   20.887(4)
_cell_angle_alpha                90
_cell_angle_beta                 97.339(17)
_cell_angle_gamma                90
_cell_volume                     2650.1(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    611
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      32.2040
_cell_measurement_theta_min      2.7610
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.959
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.99338
_exptl_absorpt_correction_T_min  0.99338
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.143a (Rigaku Oxford Diffraction, 2024)
Spherical absorption correction
using equivalent radius and absorption coefficient.
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.08
_exptl_crystal_size_rad          0.400
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0713
_diffrn_reflns_av_unetI/netI     0.0668
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            8198
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        25.028
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         2.627
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     40.00  55.00   0.50   55.00    --   25.00 -72.00 215.00   30
  2  ω    -65.00  54.50   0.50   55.00    --   25.00 -72.00 305.00  239
  3  ω    -65.00  55.00   0.50   55.00    --   25.00 -72.00 125.00  240
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'esperanto-CrysAlisPro-abstract goniometer imported esperanto images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0029239000
_diffrn_orient_matrix_UB_12      -0.0114731000
_diffrn_orient_matrix_UB_13      -0.0332556000
_diffrn_orient_matrix_UB_21      -0.0251664000
_diffrn_orient_matrix_UB_22      0.0643802000
_diffrn_orient_matrix_UB_23      -0.0075628000
_diffrn_orient_matrix_UB_31      0.0469760000
_diffrn_orient_matrix_UB_32      0.0352758000
_diffrn_orient_matrix_UB_33      0.0029717000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1491
_reflns_number_total             2291
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024) (IMPORT)'
_computing_data_reduction        'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.652
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         2291
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1272
_refine_ls_R_factor_gt           0.0934
_refine_ls_restrained_S_all      1.101
_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)+(0.1219P)²+4.1657P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2657
_refine_ls_wR_factor_ref         0.2942
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Rigid bond restraints
 C8, C9
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3. Uiso/Uaniso restraints and constraints
Uanis(C4) = Uanis(C1) = Uanis(C2) = Uanis(C3) = Uanis(C5) = Uanis(C6)
4.a Free rotating group:
 O2(H2A,H2B)
4.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C5(H5), C1(H1), C6(H6), C3(H3), C7(H7), C2(H2)
4.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C14(H14A,H14B,H14C), C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.4866(2) 0.1920(3) 0.53848(15) 0.0779(10) Uani 1 1 d . . . . .
N1 N 0.5316(2) 0.3133(3) 0.55541(14) 0.0589(9) Uani 1 1 d . . . . .
N2 N 0.6285(2) 0.4947(3) 0.55933(16) 0.0617(9) Uani 1 1 d . . . . .
O2 O 0.6179(3) -0.0356(4) 0.56521(19) 0.0945(11) Uani 1 1 d G . . . .
H2A H 0.578468 0.034447 0.561517 0.142 Uiso 1 1 d G U . . .
H2B H 0.595469 -0.089261 0.534196 0.142 Uiso 1 1 d G U . . .
C10 C 0.5132(3) 0.3902(4) 0.60788(18) 0.0618(11) Uani 1 1 d . . . . .
C9 C 0.6023(3) 0.3771(4) 0.52504(19) 0.0601(10) Uani 1 1 d . U . . .
C11 C 0.5745(3) 0.5031(4) 0.60982(19) 0.0627(11) Uani 1 1 d . . . . .
C4 C 0.6572(4) 0.1950(5) 0.3707(2) 0.0820(7) Uani 1 1 d . . . . .
C8 C 0.6426(3) 0.3367(5) 0.4673(2) 0.0718(12) Uani 1 1 d . U . . .
H8 H 0.692943 0.393645 0.454657 0.086 Uiso 1 1 calc R U . . .
C5 C 0.7368(4) 0.2589(5) 0.3467(2) 0.0820(7) Uani 1 1 d . . . . .
H5 H 0.771450 0.331377 0.369516 0.098 Uiso 1 1 calc R U . . .
C12 C 0.4378(4) 0.3446(6) 0.6495(2) 0.0949(16) Uani 1 1 d . . . . .
H12A H 0.371690 0.350674 0.625821 0.142 Uiso 1 1 calc R U . . .
H12B H 0.441657 0.404121 0.686825 0.142 Uiso 1 1 calc R U . . .
H12C H 0.451212 0.249598 0.662978 0.142 Uiso 1 1 calc R U . . .
C1 C 0.7146(4) 0.1116(5) 0.2530(2) 0.0820(7) Uani 1 1 d . . . . .
H1 H 0.732989 0.083798 0.213460 0.098 Uiso 1 1 calc R U . . .
C14 C 0.7038(4) 0.5971(5) 0.5437(3) 0.0865(15) Uani 1 1 d . . . . .
H14A H 0.763797 0.548802 0.535634 0.130 Uiso 1 1 calc R U . . .
H14B H 0.719417 0.660281 0.579316 0.130 Uiso 1 1 calc R U . . .
H14C H 0.677341 0.648968 0.505940 0.130 Uiso 1 1 calc R U . . .
C13 C 0.5881(4) 0.6190(5) 0.6579(2) 0.0863(15) Uani 1 1 d . . . . .
H13A H 0.652024 0.608891 0.684096 0.129 Uiso 1 1 calc R U . . .
H13B H 0.535277 0.615349 0.684910 0.129 Uiso 1 1 calc R U . . .
H13C H 0.585811 0.707241 0.635805 0.129 Uiso 1 1 calc R U . . .
C6 C 0.7656(4) 0.2139(5) 0.2875(2) 0.0820(7) Uani 1 1 d . . . . .
H6 H 0.820593 0.255444 0.272030 0.098 Uiso 1 1 calc R U . . .
C3 C 0.6092(4) 0.0900(5) 0.3352(2) 0.0820(7) Uani 1 1 d . . . . .
H3 H 0.556492 0.043952 0.351229 0.098 Uiso 1 1 calc R U . . .
C7 C 0.6170(4) 0.2314(5) 0.4315(2) 0.0799(13) Uani 1 1 d . . . . .
H7 H 0.568718 0.171887 0.444808 0.096 Uiso 1 1 calc R U . . .
C2 C 0.6355(4) 0.0495(5) 0.2771(2) 0.0820(7) Uani 1 1 d . . . . .
H2 H 0.599249 -0.020789 0.253657 0.098 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 N1 1.332(4) . ?
N1 C10 1.367(5) . ?
N1 C9 1.351(5) . ?
N2 C9 1.354(5) . ?
N2 C11 1.355(6) . ?
N2 C14 1.471(5) . ?
O2 H2A 0.8498 . ?
O2 H2B 0.8505 . ?
C10 C11 1.353(6) . ?
C10 C12 1.480(6) . ?
C9 C8 1.436(6) . ?
C11 C13 1.490(5) . ?
C4 C5 1.378(7) . ?
C4 C3 1.358(7) . ?
C4 C7 1.484(7) . ?
C8 H8 0.9300 . ?
C8 C7 1.273(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.408(7) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C1 H1 0.9300 . ?
C1 C6 1.347(7) . ?
C1 C2 1.366(7) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C6 H6 0.9300 . ?
C3 H3 0.9300 . ?
C3 C2 1.362(7) . ?
C7 H7 0.9300 . ?
C2 H2 0.9300 . ?

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
O1 N1 C10 123.9(3) . . ?
O1 N1 C9 126.0(3) . . ?
C9 N1 C10 110.1(3) . . ?
C9 N2 C11 109.5(3) . . ?
C9 N2 C14 124.9(4) . . ?
C11 N2 C14 125.6(4) . . ?
H2A O2 H2B 104.4 . . ?
N1 C10 C12 121.3(4) . . ?
C11 C10 N1 106.4(4) . . ?
C11 C10 C12 132.3(4) . . ?
N1 C9 N2 106.0(3) . . ?
N1 C9 C8 129.4(4) . . ?
N2 C9 C8 124.6(4) . . ?
N2 C11 C13 122.5(4) . . ?
C10 C11 N2 108.1(3) . . ?
C10 C11 C13 129.3(4) . . ?
C5 C4 C7 126.1(5) . . ?
C3 C4 C5 117.6(5) . . ?
C3 C4 C7 116.3(5) . . ?
C9 C8 H8 116.5 . . ?
C7 C8 C9 127.1(5) . . ?
C7 C8 H8 116.5 . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.7(5) . . ?
C6 C5 H5 120.1 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C6 C1 H1 120.6 . . ?
C6 C1 C2 118.8(5) . . ?
C2 C1 H1 120.6 . . ?
N2 C14 H14A 109.5 . . ?
N2 C14 H14B 109.5 . . ?
N2 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C5 C6 H6 119.5 . . ?
C1 C6 C5 120.9(5) . . ?
C1 C6 H6 119.5 . . ?
C4 C3 H3 118.7 . . ?
C4 C3 C2 122.5(5) . . ?
C2 C3 H3 118.7 . . ?
C4 C7 H7 117.0 . . ?
C8 C7 C4 126.0(5) . . ?
C8 C7 H7 117.0 . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.4(5) . . ?
C3 C2 H2 119.8 . . ?

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 N1 C10 C11 178.5(3) . . . . ?
O1 N1 C10 C12 -1.9(6) . . . . ?
O1 N1 C9 N2 -178.4(3) . . . . ?
O1 N1 C9 C8 3.3(6) . . . . ?
N1 C10 C11 N2 0.2(4) . . . . ?
N1 C10 C11 C13 -177.9(4) . . . . ?
N1 C9 C8 C7 1.9(7) . . . . ?
N2 C9 C8 C7 -176.1(4) . . . . ?
C10 N1 C9 N2 0.3(4) . . . . ?
C10 N1 C9 C8 -178.0(4) . . . . ?
C9 N1 C10 C11 -0.3(4) . . . . ?
C9 N1 C10 C12 179.3(4) . . . . ?
C9 N2 C11 C10 0.0(4) . . . . ?
C9 N2 C11 C13 178.2(3) . . . . ?
C9 C8 C7 C4 177.5(4) . . . . ?
C11 N2 C9 N1 -0.2(4) . . . . ?
C11 N2 C9 C8 178.3(3) . . . . ?
C4 C5 C6 C1 1.8(7) . . . . ?
C4 C3 C2 C1 2.1(7) . . . . ?
C5 C4 C3 C2 -1.8(7) . . . . ?
C5 C4 C7 C8 8.2(8) . . . . ?
C12 C10 C11 N2 -179.4(5) . . . . ?
C12 C10 C11 C13 2.6(7) . . . . ?
C14 N2 C9 N1 180.0(3) . . . . ?
C14 N2 C9 C8 -1.6(6) . . . . ?
C14 N2 C11 C10 179.8(4) . . . . ?
C14 N2 C11 C13 -2.0(6) . . . . ?
C6 C1 C2 C3 -0.4(7) . . . . ?
C3 C4 C5 C6 -0.2(7) . . . . ?
C3 C4 C7 C8 -170.7(5) . . . . ?
C7 C4 C5 C6 -179.1(4) . . . . ?
C7 C4 C3 C2 177.3(4) . . . . ?
C2 C1 C6 C5 -1.5(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.492
_oxdiff_exptl_absorpt_empirical_full_min 0.354
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_6b
_database_code_depnum_ccdc_archive 'CCDC 2469651'
loop_
_audit_author_name
_audit_author_address
'Ivan A. Moskalev'
;Synchrotron Radiation Facility SKIF
Russia
;
_audit_update_record             
;
2025-07-03 deposited with the CCDC.	2025-10-20 downloaded from the CCDC.
;
_audit_creation_date             2025-05-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2017/1
loop_
_audit_author_email
i.a.moskalev@srf-skif.ru
_chemical_name_common            ?
_chemical_name_systematic        
4-Acetyl-1,5-dimethyl-2-((E)-2-(4-nitrophenyl)ethenyl)-1H-imidazole
_chemical_formula_moiety         'C14 H15 N3 O3, H2 O'
_chemical_formula_sum            'C14 H17 N3 O4'
_chemical_formula_weight         291.30
_chemical_melting_point          513-515
_chemical_oxdiff_formula         'C14 H17 N3 O4'
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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'

_cell_length_a                   12.9411(8)
_cell_length_b                   8.0804(6)
_cell_length_c                   14.2750(11)
_cell_angle_alpha                90
_cell_angle_beta                 105.129(8)
_cell_angle_gamma                90
_cell_volume                     1440.99(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2040
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      32.8310
_cell_measurement_theta_min      1.8930
_cell_oxdiff_angle_alpha         90.000(5)
_cell_oxdiff_angle_beta          105.102(6)
_cell_oxdiff_angle_gamma         89.983(5)
_cell_oxdiff_length_a            12.9428(8)
_cell_oxdiff_length_b            8.0812(5)
_cell_oxdiff_length_c            14.2699(10)
_cell_oxdiff_measurement_reflns_used 1874
_cell_oxdiff_volume              1440.99(15)
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.933
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.93970
_exptl_absorpt_correction_T_min  0.93970
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.143a (Rigaku Oxford Diffraction, 2024)
Spherical absorption correction
using equivalent radius and absorption coefficient.
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_exptl_crystal_size_rad          0.400
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0724
_diffrn_reflns_av_unetI/netI     0.0667
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10865
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        25.024
_diffrn_reflns_theta_max         25.024
_diffrn_reflns_theta_min         1.893
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -65.00 115.00   0.50   56.00    --   25.00   0.00  35.00  360
  2  ω    -65.00 115.00   0.50   56.00    --   25.00   0.00 305.00  360
  3  ω    -65.00  55.00   0.50   56.00    --   25.00 -72.00  15.00  240
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'esperanto-CrysAlisPro-abstract goniometer imported esperanto images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0100018000
_diffrn_orient_matrix_UB_12      -0.0007717000
_diffrn_orient_matrix_UB_13      -0.0465580000
_diffrn_orient_matrix_UB_21      0.0545782000
_diffrn_orient_matrix_UB_22      0.0188455000
_diffrn_orient_matrix_UB_23      0.0213611000
_diffrn_orient_matrix_UB_31      0.0119318000
_diffrn_orient_matrix_UB_32      -0.0857255000
_diffrn_orient_matrix_UB_33      0.0051198000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1968
_reflns_number_total             2482
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024) (IMPORT)'
_computing_data_reduction        'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         2482
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0504
_refine_ls_restrained_S_all      1.072
_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)+(0.0692P)²+0.0883P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1396
_refine_ls_wR_factor_ref         0.1486
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C7(H7), C5(H5), C6(H6), C3(H3), C2(H2)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O3 O 0.31446(10) 0.85043(15) 0.32790(9) 0.0620(4) Uani 1 1 d . . . . .
O4 O 0.14611(13) 0.6641(2) 0.23089(12) 0.0789(5) Uani 1 1 d . . . . .
N2 N 0.30714(11) 0.89007(17) 0.41668(11) 0.0511(4) Uani 1 1 d . . . . .
N3 N 0.34398(11) 0.92529(17) 0.57245(11) 0.0529(4) Uani 1 1 d . . . . .
C9 C 0.38217(13) 0.86102(19) 0.49951(13) 0.0481(4) Uani 1 1 d . . . . .
O2 O 0.96525(14) 0.3359(2) 0.54208(19) 0.1094(7) Uani 1 1 d . . . . .
C8 C 0.48234(13) 0.7777(2) 0.51119(13) 0.0497(4) Uani 1 1 d . . . . .
H8 H 0.527951 0.773075 0.573408 0.060 Uiso 1 1 calc R U . . .
C4 C 0.61632(13) 0.6189(2) 0.45010(13) 0.0501(4) Uani 1 1 d . . . . .
C7 C 0.51549(13) 0.7062(2) 0.44003(13) 0.0520(4) Uani 1 1 d . . . . .
H7 H 0.469815 0.712707 0.377913 0.062 Uiso 1 1 calc R U . . .
N1 N 0.90174(16) 0.3546(2) 0.4634(2) 0.0852(7) Uani 1 1 d . . . . .
O1 O 0.91565(16) 0.3010(2) 0.38720(19) 0.1184(8) Uani 1 1 d . . . . .
C10 C 0.22142(14) 0.9727(2) 0.43573(16) 0.0569(5) Uani 1 1 d . . . . .
C11 C 0.24502(14) 0.9945(2) 0.53285(15) 0.0570(5) Uani 1 1 d . . . . .
C5 C 0.69302(14) 0.5976(2) 0.53790(14) 0.0565(5) Uani 1 1 d . . . . .
H5 H 0.681100 0.641972 0.594264 0.068 Uiso 1 1 calc R U . . .
C1 C 0.80305(15) 0.4470(2) 0.45890(18) 0.0628(5) Uani 1 1 d . . . . .
C6 C 0.78645(15) 0.5117(2) 0.54283(16) 0.0636(5) Uani 1 1 d . . . . .
H6 H 0.837229 0.497806 0.601831 0.076 Uiso 1 1 calc R U . . .
C3 C 0.63724(16) 0.5506(3) 0.36709(15) 0.0644(5) Uani 1 1 d . . . . .
H3 H 0.587215 0.563219 0.307540 0.077 Uiso 1 1 calc R U . . .
C2 C 0.73016(17) 0.4650(3) 0.37149(17) 0.0705(6) Uani 1 1 d . . . . .
H2 H 0.743047 0.420109 0.315622 0.085 Uiso 1 1 calc R U . . .
C13 C 0.1808(2) 1.0767(3) 0.5922(2) 0.0745(6) Uani 1 1 d . . . . .
C14 C 0.39947(17) 0.9282(3) 0.67465(16) 0.0729(6) Uani 1 1 d . . . . .
H14A H 0.461333 0.857980 0.686043 0.109 Uiso 1 1 calc R U . . .
H14B H 0.352434 0.889217 0.711903 0.109 Uiso 1 1 calc R U . . .
H14C H 0.421410 1.039400 0.693734 0.109 Uiso 1 1 calc R U . . .
C12 C 0.12670(18) 1.0205(4) 0.3568(2) 0.0767(7) Uani 1 1 d . . . . .
H13A H 0.112(2) 1.125(3) 0.544(2) 0.103(8) Uiso 1 1 d . . . . .
H13B H 0.1639(19) 1.001(3) 0.6412(19) 0.091(7) Uiso 1 1 d . . . . .
H13C H 0.220(2) 1.153(3) 0.635(2) 0.098(9) Uiso 1 1 d . . . . .
H12A H 0.077(2) 1.084(4) 0.382(2) 0.122(10) Uiso 1 1 d . . . . .
H12B H 0.148(2) 1.095(4) 0.305(2) 0.138(11) Uiso 1 1 d . . . . .
H12C H 0.089(2) 0.933(4) 0.324(2) 0.119(10) Uiso 1 1 d . . . . .
H4A H 0.209(3) 0.722(4) 0.264(2) 0.122(10) Uiso 1 1 d . . . . .
H4B H 0.166(2) 0.551(4) 0.224(2) 0.134(12) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
O3 N2 1.334(2) . ?
O4 H4A 0.95(3) . ?
O4 H4B 0.96(3) . ?
N2 C9 1.340(2) . ?
N2 C10 1.381(2) . ?
N3 C9 1.366(2) . ?
N3 C11 1.377(2) . ?
N3 C14 1.448(3) . ?
C9 C8 1.431(2) . ?
O2 N1 1.216(3) . ?
C8 H8 0.9300 . ?
C8 C7 1.333(2) . ?
C4 C7 1.457(2) . ?
C4 C5 1.392(3) . ?
C4 C3 1.396(3) . ?
C7 H7 0.9300 . ?
N1 O1 1.226(3) . ?
N1 C1 1.466(2) . ?
C10 C11 1.351(3) . ?
C10 C12 1.483(3) . ?
C11 C13 1.490(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.380(2) . ?
C1 C6 1.374(3) . ?
C1 C2 1.362(3) . ?
C6 H6 0.9300 . ?
C3 H3 0.9300 . ?
C3 C2 1.374(3) . ?
C2 H2 0.9300 . ?
C13 H13A 1.04(3) . ?
C13 H13B 0.99(3) . ?
C13 H13C 0.92(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C12 H12A 0.96(3) . ?
C12 H12B 1.05(3) . ?
C12 H12C 0.91(3) . ?

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
H4A O4 H4B 108(2) . . ?
O3 N2 C9 125.53(14) . . ?
O3 N2 C10 124.25(16) . . ?
C9 N2 C10 110.19(16) . . ?
C9 N3 C11 108.92(16) . . ?
C9 N3 C14 126.23(15) . . ?
C11 N3 C14 124.79(16) . . ?
N2 C9 N3 106.43(15) . . ?
N2 C9 C8 127.64(15) . . ?
N3 C9 C8 125.93(17) . . ?
C9 C8 H8 117.4 . . ?
C7 C8 C9 125.23(17) . . ?
C7 C8 H8 117.4 . . ?
C5 C4 C7 123.97(16) . . ?
C5 C4 C3 117.68(17) . . ?
C3 C4 C7 118.35(17) . . ?
C8 C7 C4 126.35(17) . . ?
C8 C7 H7 116.8 . . ?
C4 C7 H7 116.8 . . ?
O2 N1 O1 123.7(2) . . ?
O2 N1 C1 118.3(2) . . ?
O1 N1 C1 118.0(3) . . ?
N2 C10 C12 121.6(2) . . ?
C11 C10 N2 106.68(17) . . ?
C11 C10 C12 131.76(19) . . ?
N3 C11 C13 123.0(2) . . ?
C10 C11 N3 107.78(16) . . ?
C10 C11 C13 129.2(2) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 C4 121.19(18) . . ?
C6 C5 H5 119.4 . . ?
C6 C1 N1 119.2(2) . . ?
C2 C1 N1 118.8(2) . . ?
C2 C1 C6 121.98(17) . . ?
C5 C6 H6 120.6 . . ?
C1 C6 C5 118.75(19) . . ?
C1 C6 H6 120.6 . . ?
C4 C3 H3 119.3 . . ?
C2 C3 C4 121.4(2) . . ?
C2 C3 H3 119.3 . . ?
C1 C2 C3 118.98(19) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C11 C13 H13A 107.2(15) . . ?
C11 C13 H13B 112.6(14) . . ?
C11 C13 H13C 112.4(17) . . ?
H13A C13 H13B 113(2) . . ?
H13A C13 H13C 114(2) . . ?
H13B C13 H13C 97(2) . . ?
N3 C14 H14A 109.5 . . ?
N3 C14 H14B 109.5 . . ?
N3 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C10 C12 H12A 110.6(18) . . ?
C10 C12 H12B 111.8(17) . . ?
C10 C12 H12C 114(2) . . ?
H12A C12 H12B 107(3) . . ?
H12A C12 H12C 107(3) . . ?
H12B C12 H12C 106(3) . . ?

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
O3 N2 C9 N3 178.19(14) . . . . ?
O3 N2 C9 C8 -2.5(3) . . . . ?
O3 N2 C10 C11 -178.02(15) . . . . ?
O3 N2 C10 C12 2.0(3) . . . . ?
N2 C9 C8 C7 -3.8(3) . . . . ?
N2 C10 C11 N3 -0.22(19) . . . . ?
N2 C10 C11 C13 179.8(2) . . . . ?
N3 C9 C8 C7 175.40(16) . . . . ?
C9 N2 C10 C11 0.03(19) . . . . ?
C9 N2 C10 C12 180.00(18) . . . . ?
C9 N3 C11 C10 0.3(2) . . . . ?
C9 N3 C11 C13 -179.69(18) . . . . ?
C9 C8 C7 C4 -179.17(15) . . . . ?
O2 N1 C1 C6 1.2(3) . . . . ?
O2 N1 C1 C2 -178.34(18) . . . . ?
C4 C5 C6 C1 0.1(3) . . . . ?
C4 C3 C2 C1 0.0(3) . . . . ?
C7 C4 C5 C6 179.15(16) . . . . ?
C7 C4 C3 C2 -179.25(17) . . . . ?
N1 C1 C6 C5 -179.63(16) . . . . ?
N1 C1 C2 C3 179.58(17) . . . . ?
O1 N1 C1 C6 -178.55(19) . . . . ?
O1 N1 C1 C2 1.9(3) . . . . ?
C10 N2 C9 N3 0.17(19) . . . . ?
C10 N2 C9 C8 179.45(15) . . . . ?
C11 N3 C9 N2 -0.30(19) . . . . ?
C11 N3 C9 C8 -179.60(15) . . . . ?
C5 C4 C7 C8 0.3(3) . . . . ?
C5 C4 C3 C2 0.0(3) . . . . ?
C6 C1 C2 C3 0.0(3) . . . . ?
C3 C4 C7 C8 179.57(18) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
C2 C1 C6 C5 -0.1(3) . . . . ?
C14 N3 C9 N2 -177.63(15) . . . . ?
C14 N3 C9 C8 3.1(3) . . . . ?
C14 N3 C11 C10 177.71(16) . . . . ?
C14 N3 C11 C13 -2.3(3) . . . . ?
C12 C10 C11 N3 179.8(2) . . . . ?
C12 C10 C11 C13 -0.2(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.914
_oxdiff_exptl_absorpt_empirical_full_min 0.167
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4c
_database_code_depnum_ccdc_archive 'CCDC 2469648'
loop_
_audit_author_name
_audit_author_address
'Ivan A. Moskalev'
;Synchrotron Radiation Facility SKIF
Russia
;
_audit_update_record             
;
2025-07-03 deposited with the CCDC.	2025-10-20 downloaded from the CCDC.
;
_audit_creation_date             2025-05-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2017/1
loop_
_audit_author_email
i.a.moskalev@srf-skif.ru
_chemical_name_common            ?
_chemical_name_systematic        Ethyl
_chemical_formula_moiety         'C16 H18 N3 O5'
_chemical_formula_sum            'C16 H18 N3 O5'
_chemical_formula_weight         332.33
_chemical_melting_point          431-433
_chemical_oxdiff_formula         'C17 H16 N3 O5'
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   4.7308(9)
_cell_length_b                   38.246(3)
_cell_length_c                   9.089(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.796(17)
_cell_angle_gamma                90
_cell_volume                     1632.9(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    456
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      32.5630
_cell_measurement_theta_min      2.4880
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.93732
_exptl_absorpt_correction_T_min  0.93732
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.143a (Rigaku Oxford Diffraction, 2024)
Spherical absorption correction
using equivalent radius and absorption coefficient.
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             700
_exptl_crystal_size_max          0.84
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_exptl_crystal_size_rad          0.400
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1165
_diffrn_reflns_av_unetI/netI     0.1059
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       45
_diffrn_reflns_limit_k_min       -45
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            11371
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         2.319
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -65.00 115.00   0.50   94.00    --   25.00   0.00  35.00  360
  2  ω    -65.00  55.00   0.50   94.00    --   25.00   0.00 125.00  240
  3  ω    -65.00  44.50   0.50   94.00    --   25.00 -72.00 185.00  219
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'esperanto-CrysAlisPro-abstract goniometer imported esperanto images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0161649000
_diffrn_orient_matrix_UB_12      0.0180043000
_diffrn_orient_matrix_UB_13      -0.0178028000
_diffrn_orient_matrix_UB_21      -0.0160963000
_diffrn_orient_matrix_UB_22      -0.0042005000
_diffrn_orient_matrix_UB_23      -0.0765397000
_diffrn_orient_matrix_UB_31      -0.1491557000
_diffrn_orient_matrix_UB_32      -0.0014968000
_diffrn_orient_matrix_UB_33      0.0007918000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1581
_reflns_number_total             2799
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024) (IMPORT)'
_computing_data_reduction        'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         2799
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1321
_refine_ls_R_factor_gt           0.0799
_refine_ls_restrained_S_all      1.009
_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)+(0.1558P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2336
_refine_ls_wR_factor_ref         0.2738
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 O5, C13
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
 N3, C9
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
3.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C8(H8), C7(H7), C6(H6), C2(H2), C5(H5), C3(H3A)
3.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C16(H16A,H16B,H16C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O3 O -0.0421(5) 0.64473(9) 0.1685(3) 0.0745(9) Uani 1 1 d . . . . .
N1 N 1.2875(7) 0.73597(10) 0.8265(4) 0.0681(10) Uani 1 1 d . . . . .
O1 O 1.2836(7) 0.76516(10) 0.7742(4) 0.0987(12) Uani 1 1 d . . . . .
N2 N -0.0857(7) 0.61925(9) 0.2702(4) 0.0648(9) Uani 1 1 d . . . . .
N3 N -0.0045(7) 0.58739(9) 0.4701(4) 0.0698(9) Uani 1 1 d . U . . .
H3 H 0.063765 0.579965 0.556348 0.084 Uiso 1 1 calc R U . . .
O2 O 1.4588(7) 0.72692(10) 0.9288(4) 0.1004(12) Uani 1 1 d . . . . .
O4 O -0.5043(8) 0.60938(13) 0.0133(4) 0.1099(13) Uani 1 1 d . . . . .
O5 O -0.6160(8) 0.55817(10) 0.1139(5) 0.1120(13) Uani 1 1 d . U . . .
C1 C 1.0763(7) 0.71046(10) 0.7638(4) 0.0558(9) Uani 1 1 d . . . . .
C9 C 0.0726(8) 0.61590(11) 0.4034(4) 0.0604(10) Uani 1 1 d . U . . .
C8 C 0.2818(7) 0.64105(10) 0.4581(4) 0.0592(10) Uani 1 1 d . . . . .
H8 H 0.296842 0.661183 0.402129 0.071 Uiso 1 1 calc R U . . .
C4 C 0.6698(7) 0.66343(10) 0.6440(4) 0.0545(9) Uani 1 1 d . . . . .
C7 C 0.4563(7) 0.63786(10) 0.5827(4) 0.0587(10) Uani 1 1 d . . . . .
H7 H 0.441984 0.617401 0.636629 0.070 Uiso 1 1 calc R U . . .
C6 C 1.0629(8) 0.67811(11) 0.8278(4) 0.0600(10) Uani 1 1 d . . . . .
H6 H 1.188793 0.672121 0.910374 0.072 Uiso 1 1 calc R U . . .
C2 C 0.8913(8) 0.72038(10) 0.6405(4) 0.0604(10) Uani 1 1 d . . . . .
H2 H 0.902255 0.742461 0.598728 0.072 Uiso 1 1 calc R U . . .
C5 C 0.8621(8) 0.65483(11) 0.7685(4) 0.0640(11) Uani 1 1 d . . . . .
H5 H 0.852539 0.632849 0.811409 0.077 Uiso 1 1 calc R U . . .
C3 C 0.6916(8) 0.69646(10) 0.5823(4) 0.0577(10) Uani 1 1 d . . . . .
H3A H 0.567367 0.702552 0.499218 0.069 Uiso 1 1 calc R U . . .
C13 C -0.4723(9) 0.58812(13) 0.1071(6) 0.0793(13) Uani 1 1 d . U . . .
C10 C -0.2725(8) 0.59120(12) 0.2491(5) 0.0695(12) Uani 1 1 d . . . . .
C11 C -0.2140(8) 0.57193(11) 0.3754(6) 0.0730(13) Uani 1 1 d . . . . .
C12 C -0.2382(10) 0.67331(13) 0.1768(5) 0.0830(13) Uani 1 1 d . . . . .
H12A H -0.212031 0.690148 0.101234 0.125 Uiso 1 1 calc R U . . .
H12B H -0.203305 0.684197 0.272371 0.125 Uiso 1 1 calc R U . . .
H12C H -0.429845 0.664618 0.162221 0.125 Uiso 1 1 calc R U . . .
C16 C -0.3516(12) 0.53926(13) 0.4218(7) 0.1035(17) Uani 1 1 d . . . . .
H16A H -0.252595 0.531108 0.513679 0.155 Uiso 1 1 calc R U . . .
H16B H -0.344105 0.521663 0.347000 0.155 Uiso 1 1 calc R U . . .
H16C H -0.546498 0.543990 0.434440 0.155 Uiso 1 1 calc R U . . .
C14 C -0.8315(14) 0.5549(2) -0.0205(8) 0.142(3) Uani 1 1 d . . . . .
H14A H -0.983164 0.539353 0.000903 0.170 Uiso 1 1 calc R U . . .
H14B H -0.914293 0.577681 -0.045668 0.170 Uiso 1 1 calc R U . . .
C15 C -0.6970(19) 0.5412(3) -0.1468(9) 0.207(5) Uani 1 1 d . . . . .
H15A H -0.835325 0.540280 -0.232934 0.310 Uiso 1 1 calc R U . . .
H15B H -0.624850 0.518151 -0.123815 0.310 Uiso 1 1 calc R U . . .
H15C H -0.543167 0.556288 -0.165833 0.310 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
O3 N2 1.375(4) . ?
O3 C12 1.441(5) . ?
N1 O1 1.213(5) . ?
N1 O2 1.209(4) . ?
N1 C1 1.463(5) . ?
N2 C9 1.352(5) . ?
N2 C10 1.389(5) . ?
N3 H3 0.8600 . ?
N3 C9 1.320(5) . ?
N3 C11 1.367(5) . ?
O4 C13 1.175(6) . ?
O5 C13 1.337(6) . ?
O5 C14 1.500(7) . ?
C1 C6 1.372(5) . ?
C1 C2 1.391(5) . ?
C9 C8 1.426(5) . ?
C8 H8 0.9300 . ?
C8 C7 1.326(5) . ?
C4 C7 1.467(5) . ?
C4 C5 1.405(5) . ?
C4 C3 1.391(5) . ?
C7 H7 0.9300 . ?
C6 H6 0.9300 . ?
C6 C5 1.365(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.375(5) . ?
C5 H5 0.9300 . ?
C3 H3A 0.9300 . ?
C13 C10 1.512(6) . ?
C10 C11 1.365(6) . ?
C11 C16 1.492(6) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.473(10) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

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
N2 O3 C12 110.7(3) . . ?
O1 N1 C1 118.9(3) . . ?
O2 N1 O1 122.9(4) . . ?
O2 N1 C1 118.2(4) . . ?
O3 N2 C10 126.7(3) . . ?
C9 N2 O3 123.9(3) . . ?
C9 N2 C10 109.1(4) . . ?
C9 N3 H3 126.6 . . ?
C9 N3 C11 106.7(4) . . ?
C11 N3 H3 126.6 . . ?
C13 O5 C14 109.4(5) . . ?
C6 C1 N1 120.0(3) . . ?
C6 C1 C2 122.1(3) . . ?
C2 C1 N1 117.9(4) . . ?
N2 C9 C8 122.4(4) . . ?
N3 C9 N2 109.6(3) . . ?
N3 C9 C8 128.0(4) . . ?
C9 C8 H8 117.6 . . ?
C7 C8 C9 124.9(4) . . ?
C7 C8 H8 117.6 . . ?
C5 C4 C7 120.0(4) . . ?
C3 C4 C7 122.2(3) . . ?
C3 C4 C5 117.8(3) . . ?
C8 C7 C4 126.4(4) . . ?
C8 C7 H7 116.8 . . ?
C4 C7 H7 116.8 . . ?
C1 C6 H6 120.5 . . ?
C5 C6 C1 119.1(3) . . ?
C5 C6 H6 120.5 . . ?
C1 C2 H2 121.1 . . ?
C3 C2 C1 117.8(4) . . ?
C3 C2 H2 121.1 . . ?
C4 C5 H5 119.4 . . ?
C6 C5 C4 121.3(4) . . ?
C6 C5 H5 119.4 . . ?
C4 C3 H3A 119.0 . . ?
C2 C3 C4 122.0(3) . . ?
C2 C3 H3A 119.0 . . ?
O4 C13 O5 127.2(5) . . ?
O4 C13 C10 125.4(5) . . ?
O5 C13 C10 107.3(5) . . ?
N2 C10 C13 120.1(4) . . ?
C11 C10 N2 103.8(4) . . ?
C11 C10 C13 136.1(4) . . ?
N3 C11 C16 119.5(5) . . ?
C10 C11 N3 110.8(4) . . ?
C10 C11 C16 129.6(4) . . ?
O3 C12 H12A 109.5 . . ?
O3 C12 H12B 109.5 . . ?
O3 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C16 H16A 109.5 . . ?
C11 C16 H16B 109.5 . . ?
C11 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O5 C14 H14A 109.6 . . ?
O5 C14 H14B 109.6 . . ?
H14A C14 H14B 108.1 . . ?
C15 C14 O5 110.4(6) . . ?
C15 C14 H14A 109.6 . . ?
C15 C14 H14B 109.6 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

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
O3 N2 C9 N3 -174.6(3) . . . . ?
O3 N2 C9 C8 7.1(6) . . . . ?
O3 N2 C10 C13 -5.3(6) . . . . ?
O3 N2 C10 C11 173.7(3) . . . . ?
N1 C1 C6 C5 179.3(3) . . . . ?
N1 C1 C2 C3 -179.6(3) . . . . ?
O1 N1 C1 C6 -175.3(4) . . . . ?
O1 N1 C1 C2 3.9(5) . . . . ?
N2 C9 C8 C7 -175.0(4) . . . . ?
N2 C10 C11 N3 0.6(4) . . . . ?
N2 C10 C11 C16 177.5(5) . . . . ?
N3 C9 C8 C7 7.0(7) . . . . ?
O2 N1 C1 C6 4.7(5) . . . . ?
O2 N1 C1 C2 -176.1(4) . . . . ?
O4 C13 C10 N2 -6.9(7) . . . . ?
O4 C13 C10 C11 174.4(5) . . . . ?
O5 C13 C10 N2 177.1(4) . . . . ?
O5 C13 C10 C11 -1.5(7) . . . . ?
C1 C6 C5 C4 -0.1(6) . . . . ?
C1 C2 C3 C4 0.6(6) . . . . ?
C9 N2 C10 C13 -179.0(4) . . . . ?
C9 N2 C10 C11 0.1(4) . . . . ?
C9 N3 C11 C10 -1.0(5) . . . . ?
C9 N3 C11 C16 -178.3(4) . . . . ?
C9 C8 C7 C4 -178.7(3) . . . . ?
C7 C4 C5 C6 180.0(3) . . . . ?
C7 C4 C3 C2 179.7(3) . . . . ?
C6 C1 C2 C3 -0.4(6) . . . . ?
C2 C1 C6 C5 0.1(6) . . . . ?
C5 C4 C7 C8 -172.8(4) . . . . ?
C5 C4 C3 C2 -0.6(6) . . . . ?
C3 C4 C7 C8 6.9(6) . . . . ?
C3 C4 C5 C6 0.4(6) . . . . ?
C13 O5 C14 C15 82.5(8) . . . . ?
C13 C10 C11 N3 179.4(5) . . . . ?
C13 C10 C11 C16 -3.7(9) . . . . ?
C10 N2 C9 N3 -0.7(5) . . . . ?
C10 N2 C9 C8 -179.0(3) . . . . ?
C11 N3 C9 N2 1.1(5) . . . . ?
C11 N3 C9 C8 179.2(4) . . . . ?
C12 O3 N2 C9 -98.9(4) . . . . ?
C12 O3 N2 C10 88.4(4) . . . . ?
C14 O5 C13 O4 0.5(8) . . . . ?
C14 O5 C13 C10 176.3(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.676
_oxdiff_exptl_absorpt_empirical_full_min 0.192
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3c
_database_code_depnum_ccdc_archive 'CCDC 2469647'
loop_
_audit_author_name
_audit_author_address
'Ivan A. Moskalev'
;Synchrotron Radiation Facility SKIF
Russia
;
_audit_update_record             
;
2025-07-03 deposited with the CCDC.	2025-10-20 downloaded from the CCDC.
;
_audit_creation_date             2025-07-03
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2017/1
loop_
_audit_author_email
i.a.moskalev@srf-skif.ru
_chemical_name_common            ?
_chemical_name_systematic        
'Ethyl 1-hydroxy-4-methyl-2-((E)-2-(4-nitrophenyl)ethenyl)-1H-imidazole-5-carboxylate'
_chemical_formula_moiety         'C15 H15 N3 O5, C15 H14 N3 O5'
_chemical_formula_sum            'C30 H29 N6 O10'
_chemical_formula_weight         633.59
_chemical_melting_point          478-480
_chemical_oxdiff_formula         'C15 H15 N3 O5'
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.3738(5)
_cell_length_b                   14.1463(10)
_cell_length_c                   15.4463(10)
_cell_angle_alpha                66.399(6)
_cell_angle_beta                 88.379(5)
_cell_angle_gamma                86.836(5)
_cell_volume                     1474.18(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3424
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      33.7200
_cell_measurement_theta_min      1.5680
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.902
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69651
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             662
_exptl_crystal_size_max          0.96
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1072
_diffrn_reflns_av_unetI/netI     0.1307
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.808
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            29468
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.808
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.735
_diffrn_reflns_theta_min         1.573
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.808
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -65.00 115.00   0.50   75.00    --   25.00   0.00  35.00  360
  2  ω    -65.00 115.00   0.50   75.00    --   25.00   0.00 125.00  360
  3  ω    -65.00  54.50   0.50   75.00    --   25.00 -72.00  30.00  239
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'esperanto-CrysAlisPro-abstract goniometer imported esperanto images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0012968000
_diffrn_orient_matrix_UB_12      0.0178729000
_diffrn_orient_matrix_UB_13      -0.0499434000
_diffrn_orient_matrix_UB_21      -0.0045044000
_diffrn_orient_matrix_UB_22      -0.0515595000
_diffrn_orient_matrix_UB_23      0.0040389000
_diffrn_orient_matrix_UB_31      -0.0962266000
_diffrn_orient_matrix_UB_32      0.0047993000
_diffrn_orient_matrix_UB_33      0.0008234000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4312
_reflns_number_total             9515
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.980
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     420
_refine_ls_number_reflns         9515
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1585
_refine_ls_R_factor_gt           0.0880
_refine_ls_restrained_S_all      0.984
_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)+(0.1203P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2362
_refine_ls_wR_factor_ref         0.2942
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
C6 \\sim C1: within 1.7A with sigma of 0.002 and sigma for terminal atoms of
0.004 within 1.7A
3.a Secondary CH2 refined with riding coordinates:
 C14(H14a,H14b)
3.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C23(H23), C22(H22), C18(H18), C20(H20), C7(H7), C8(H8), C17(H17),
 C21(H21), C3(H3), C2(H2a), C5(H5), C6(H6), C29(H29)
3.c Idealised Me refined as rotating group:
 C27(H27a,H27b,H27c), C12(H12a,H12b,H12c), C15(H15a,H15b,H15c), C30(H30a,H30b,
 H30c)
3.d Idealised tetrahedral OH refined as rotating group:
 O8(H8a)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O3 O 0.1743(2) 0.65323(12) 0.49433(12) 0.0633(5) Uani 1 1 d . . . . .
O8 O 0.4234(2) 0.78571(12) 0.43876(13) 0.0632(5) Uani 1 1 d . . . . .
H8A H 0.346157 0.742271 0.457049 0.095 Uiso 1 1 calc R U . . .
N5 N 0.2367(3) 1.03406(14) 0.30564(13) 0.0520(4) Uani 1 1 d . . . . .
O5 O 0.0977(3) 0.63665(13) 0.77667(13) 0.0703(5) Uani 1 1 d . . . . .
N6 N 0.3509(2) 0.87482(14) 0.37068(13) 0.0493(4) Uani 1 1 d . . . . .
N3 N 0.2010(3) 0.57332(14) 0.57559(14) 0.0515(4) Uani 1 1 d . . . . .
O4 O 0.1215(3) 0.75127(14) 0.62749(14) 0.0812(6) Uani 1 1 d . . . . .
N2 N 0.2545(3) 0.41694(15) 0.67620(14) 0.0626(5) Uani 1 1 d . . . . .
H2 H 0.283417 0.351875 0.699103 0.075 Uiso 1 1 calc R U . . .
O9 O 0.4805(3) 0.74591(17) 0.26945(17) 0.0958(7) Uani 1 1 d . . . . .
O10 O 0.3581(4) 0.86709(19) 0.14125(16) 0.1037(8) Uani 1 1 d . . . . .
C19 C 0.1958(3) 1.05860(17) 0.57897(16) 0.0499(5) Uani 1 1 d . . . . .
C24 C 0.2915(3) 0.95817(17) 0.38624(16) 0.0488(5) Uani 1 1 d . . . . .
C23 C 0.2851(3) 0.96279(17) 0.47791(15) 0.0493(5) Uani 1 1 d . . . . .
H23 H 0.335543 0.907681 0.529263 0.059 Uiso 1 1 calc R U . . .
C22 C 0.2097(3) 1.04290(17) 0.49111(16) 0.0506(5) Uani 1 1 d . . . . .
H22 H 0.159452 1.095752 0.437999 0.061 Uiso 1 1 calc R U . . .
C9 C 0.2486(3) 0.47788(18) 0.58267(18) 0.0543(5) Uani 1 1 d . . . . .
N1 N 0.4447(4) 0.3341(3) 0.1369(2) 0.0845(8) Uani 1 1 d . . . . .
C25 C 0.2641(3) 0.99786(17) 0.23710(16) 0.0505(5) Uani 1 1 d . . . . .
O6 O 0.0892(4) 1.2058(2) 0.81659(19) 0.1186(10) Uani 1 1 d . . . . .
N4 N 0.1509(4) 1.1210(2) 0.82480(19) 0.0819(8) Uani 1 1 d . . . . .
O1 O 0.4991(4) 0.2445(2) 0.1620(2) 0.1105(9) Uani 1 1 d . . . . .
C11 C 0.1747(3) 0.57160(16) 0.66588(16) 0.0520(5) Uani 1 1 d . . . . .
C26 C 0.3372(3) 0.89693(16) 0.27552(16) 0.0498(5) Uani 1 1 d . . . . .
C13 C 0.1282(3) 0.66407(18) 0.68472(17) 0.0537(5) Uani 1 1 d . . . . .
C4 C 0.3133(3) 0.4487(2) 0.34733(17) 0.0574(6) Uani 1 1 d . . . . .
C10 C 0.2094(3) 0.47129(17) 0.72892(18) 0.0565(6) Uani 1 1 d . . . . .
C18 C 0.1064(3) 1.14946(18) 0.57677(17) 0.0547(5) Uani 1 1 d . . . . .
H18 H 0.055748 1.196521 0.520526 0.066 Uiso 1 1 calc R U . . .
C20 C 0.2703(3) 0.9882(2) 0.66444(17) 0.0574(6) Uani 1 1 d . . . . .
H20 H 0.330511 0.927645 0.666918 0.069 Uiso 1 1 calc R U . . .
C7 C 0.2742(3) 0.4917(2) 0.41858(19) 0.0613(6) Uani 1 1 d . . . . .
H7 H 0.239299 0.561519 0.396836 0.074 Uiso 1 1 calc R U . . .
C16 C 0.1666(4) 1.0989(2) 0.73943(18) 0.0616(6) Uani 1 1 d . . . . .
C8 C 0.2847(3) 0.43928(19) 0.51091(18) 0.0595(6) Uani 1 1 d . . . . .
H8 H 0.319373 0.369544 0.531622 0.071 Uiso 1 1 calc R U . . .
C17 C 0.0922(3) 1.1703(2) 0.65686(19) 0.0606(6) Uani 1 1 d . . . . .
H17 H 0.033765 1.231039 0.655014 0.073 Uiso 1 1 calc R U . . .
C21 C 0.2550(3) 1.0081(2) 0.74527(17) 0.0604(6) Uani 1 1 d . . . . .
H21 H 0.303215 0.961159 0.802224 0.072 Uiso 1 1 calc R U . . .
C1 C 0.3938(4) 0.3738(2) 0.20943(19) 0.0658(6) Uani 1 1 d . U . . .
C28 C 0.4007(4) 0.8281(2) 0.2312(2) 0.0618(6) Uani 1 1 d . . . . .
C3 C 0.3525(4) 0.3434(2) 0.37113(19) 0.0646(6) Uani 1 1 d . . . . .
H3 H 0.350171 0.297863 0.434312 0.078 Uiso 1 1 calc R U . . .
O2 O 0.4255(5) 0.3931(3) 0.0546(2) 0.1342(11) Uani 1 1 d . . . . .
C27 C 0.2164(4) 1.0647(2) 0.13724(18) 0.0728(7) Uani 1 1 d . . . . .
H27A H 0.086935 1.068654 0.129953 0.109 Uiso 1 1 calc R U . . .
H27B H 0.273014 1.035758 0.096043 0.109 Uiso 1 1 calc R U . . .
H27C H 0.258369 1.132698 0.121422 0.109 Uiso 1 1 calc R U . . .
C12 C 0.1998(4) 0.4214(2) 0.83432(18) 0.0718(7) Uani 1 1 d . . . . .
H12A H 0.076194 0.424466 0.854685 0.108 Uiso 1 1 calc R U . . .
H12B H 0.273736 0.457127 0.860434 0.108 Uiso 1 1 calc R U . . .
H12C H 0.243239 0.350577 0.855550 0.108 Uiso 1 1 calc R U . . .
C14 C 0.0540(4) 0.7168(2) 0.8099(2) 0.0699(7) Uani 1 1 d . . . . .
H14A H -0.058523 0.753942 0.782141 0.084 Uiso 1 1 calc R U . . .
H14B H 0.149957 0.765361 0.793168 0.084 Uiso 1 1 calc R U . . .
O7 O 0.2063(5) 1.0555(3) 0.89916(19) 0.1314(11) Uani 1 1 d . . . . .
C2 C 0.3950(4) 0.3055(2) 0.30251(19) 0.0666(7) Uani 1 1 d . . . . .
H2A H 0.423502 0.235623 0.319141 0.080 Uiso 1 1 calc R U . . .
C5 C 0.3107(4) 0.5141(2) 0.2527(2) 0.0756(8) Uani 1 1 d . . . . .
H5 H 0.281155 0.583978 0.235322 0.091 Uiso 1 1 calc R U . . .
C6 C 0.3512(4) 0.4774(2) 0.1831(2) 0.0755(7) Uani 1 1 d . U . . .
H6 H 0.349615 0.522242 0.119641 0.091 Uiso 1 1 calc R U . . .
C15 C 0.0350(5) 0.6650(3) 0.9141(2) 0.0890(9) Uani 1 1 d . . . . .
H15A H -0.055766 0.614514 0.929669 0.133 Uiso 1 1 calc R U . . .
H15B H -0.000621 0.715380 0.939155 0.133 Uiso 1 1 calc R U . . .
H15C H 0.149064 0.631531 0.940892 0.133 Uiso 1 1 calc R U . . .
C29 C 0.4233(6) 0.8144(4) 0.0819(3) 0.1245(16) Uani 1 1 d . . . . .
H29 H 0.543739 0.793451 0.077449 0.149 Uiso 1 1 calc R U . . .
C30 C 0.2834(7) 0.8003(4) 0.0340(3) 0.159(2) Uani 1 1 d . . . . .
H30A H 0.326323 0.760741 -0.001150 0.239 Uiso 1 1 calc R U . . .
H30B H 0.233696 0.866175 -0.008690 0.239 Uiso 1 1 calc R U . . .
H30C H 0.190983 0.763901 0.077870 0.239 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
O3 N3 1.321(2) . ?
O8 H8A 0.8200 . ?
O8 N6 1.370(2) . ?
N5 C24 1.333(3) . ?
N5 C25 1.355(3) . ?
O5 C13 1.330(3) . ?
O5 C14 1.438(3) . ?
N6 C24 1.343(3) . ?
N6 C26 1.380(3) . ?
N3 C9 1.338(3) . ?
N3 C11 1.393(3) . ?
O4 C13 1.195(3) . ?
N2 H2 0.8600 . ?
N2 C9 1.354(3) . ?
N2 C10 1.350(3) . ?
O9 C28 1.200(3) . ?
O10 C28 1.314(3) . ?
O10 C29 1.452(4) . ?
C19 C22 1.460(3) . ?
C19 C18 1.400(3) . ?
C19 C20 1.402(3) . ?
C24 C23 1.443(3) . ?
C23 H23 0.9300 . ?
C23 C22 1.320(3) . ?
C22 H22 0.9300 . ?
C9 C8 1.432(3) . ?
N1 O1 1.216(4) . ?
N1 C1 1.472(4) . ?
N1 O2 1.217(4) . ?
C25 C26 1.392(3) . ?
C25 C27 1.491(3) . ?
O6 N4 1.218(4) . ?
N4 C16 1.472(3) . ?
N4 O7 1.216(4) . ?
C11 C13 1.471(3) . ?
C11 C10 1.376(3) . ?
C26 C28 1.449(3) . ?
C4 C7 1.471(4) . ?
C4 C3 1.399(4) . ?
C4 C5 1.381(3) . ?
C10 C12 1.494(3) . ?
C18 H18 0.9300 . ?
C18 C17 1.382(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.386(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.320(4) . ?
C16 C17 1.376(4) . ?
C16 C21 1.380(4) . ?
C8 H8 0.9300 . ?
C17 H17 0.9300 . ?
C21 H21 0.9300 . ?
C1 C2 1.374(4) . ?
C1 C6 1.376(4) . ?
C3 H3 0.9300 . ?
C3 C2 1.388(4) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.483(4) . ?
C2 H2A 0.9300 . ?
C5 H5 0.9300 . ?
C5 C6 1.387(4) . ?
C6 H6 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C29 H29 0.9300 . ?
C29 C30 1.356(6) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?

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
N6 O8 H8A 109.5 . . ?
C24 N5 C25 106.59(19) . . ?
C13 O5 C14 118.20(19) . . ?
O8 N6 C26 126.66(18) . . ?
C24 N6 O8 124.30(19) . . ?
C24 N6 C26 108.92(18) . . ?
O3 N3 C9 123.7(2) . . ?
O3 N3 C11 127.06(19) . . ?
C9 N3 C11 109.11(19) . . ?
C9 N2 H2 124.3 . . ?
C10 N2 H2 124.3 . . ?
C10 N2 C9 111.4(2) . . ?
C28 O10 C29 119.5(3) . . ?
C18 C19 C22 118.1(2) . . ?
C18 C19 C20 118.8(2) . . ?
C20 C19 C22 123.2(2) . . ?
N5 C24 N6 110.2(2) . . ?
N5 C24 C23 125.5(2) . . ?
N6 C24 C23 124.2(2) . . ?
C24 C23 H23 119.0 . . ?
C22 C23 C24 122.0(2) . . ?
C22 C23 H23 119.0 . . ?
C19 C22 H22 116.1 . . ?
C23 C22 C19 127.9(2) . . ?
C23 C22 H22 116.1 . . ?
N3 C9 N2 106.5(2) . . ?
N3 C9 C8 130.5(2) . . ?
N2 C9 C8 123.0(2) . . ?
O1 N1 C1 118.8(3) . . ?
O1 N1 O2 123.7(3) . . ?
O2 N1 C1 117.5(3) . . ?
N5 C25 C26 110.2(2) . . ?
N5 C25 C27 120.2(2) . . ?
C26 C25 C27 129.6(2) . . ?
O6 N4 C16 118.1(3) . . ?
O7 N4 O6 123.2(3) . . ?
O7 N4 C16 118.6(3) . . ?
N3 C11 C13 123.8(2) . . ?
C10 C11 N3 107.0(2) . . ?
C10 C11 C13 129.1(2) . . ?
N6 C26 C25 104.02(19) . . ?
N6 C26 C28 124.7(2) . . ?
C25 C26 C28 131.2(2) . . ?
O5 C13 C11 109.63(19) . . ?
O4 C13 O5 124.3(2) . . ?
O4 C13 C11 126.1(2) . . ?
C3 C4 C7 122.7(2) . . ?
C5 C4 C7 119.3(2) . . ?
C5 C4 C3 118.0(3) . . ?
N2 C10 C11 106.0(2) . . ?
N2 C10 C12 122.1(2) . . ?
C11 C10 C12 131.9(2) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 C19 121.0(2) . . ?
C17 C18 H18 119.5 . . ?
C19 C20 H20 119.7 . . ?
C21 C20 C19 120.5(2) . . ?
C21 C20 H20 119.7 . . ?
C4 C7 H7 117.4 . . ?
C8 C7 C4 125.3(2) . . ?
C8 C7 H7 117.4 . . ?
C17 C16 N4 118.4(3) . . ?
C17 C16 C21 122.7(2) . . ?
C21 C16 N4 118.9(3) . . ?
C9 C8 H8 116.4 . . ?
C7 C8 C9 127.2(2) . . ?
C7 C8 H8 116.4 . . ?
C18 C17 H17 120.8 . . ?
C16 C17 C18 118.4(2) . . ?
C16 C17 H17 120.8 . . ?
C20 C21 H21 120.7 . . ?
C16 C21 C20 118.6(2) . . ?
C16 C21 H21 120.7 . . ?
C2 C1 N1 118.4(3) . . ?
C2 C1 C6 121.8(3) . . ?
C6 C1 N1 119.8(3) . . ?
O9 C28 O10 123.0(2) . . ?
O9 C28 C26 126.2(3) . . ?
O10 C28 C26 110.8(2) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 C4 121.4(3) . . ?
C2 C3 H3 119.3 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O5 C14 H14A 110.4 . . ?
O5 C14 H14B 110.4 . . ?
O5 C14 C15 106.6(2) . . ?
H14A C14 H14B 108.6 . . ?
C15 C14 H14A 110.4 . . ?
C15 C14 H14B 110.4 . . ?
C1 C2 C3 118.4(3) . . ?
C1 C2 H2A 120.8 . . ?
C3 C2 H2A 120.8 . . ?
C4 C5 H5 119.3 . . ?
C4 C5 C6 121.3(3) . . ?
C6 C5 H5 119.3 . . ?
C1 C6 C5 118.9(3) . . ?
C1 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O10 C29 H29 124.9 . . ?
C30 C29 O10 110.2(4) . . ?
C30 C29 H29 124.9 . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?

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
O3 N3 C9 N2 -177.18(19) . . . . ?
O3 N3 C9 C8 1.4(4) . . . . ?
O3 N3 C11 C13 -6.2(4) . . . . ?
O3 N3 C11 C10 176.7(2) . . . . ?
O8 N6 C24 N5 177.04(18) . . . . ?
O8 N6 C24 C23 -4.2(3) . . . . ?
O8 N6 C26 C25 -176.78(19) . . . . ?
O8 N6 C26 C28 -0.7(3) . . . . ?
N5 C24 C23 C22 5.1(3) . . . . ?
N5 C25 C26 N6 0.4(3) . . . . ?
N5 C25 C26 C28 -175.4(2) . . . . ?
N6 C24 C23 C22 -173.5(2) . . . . ?
N6 C26 C28 O9 -3.8(4) . . . . ?
N6 C26 C28 O10 175.7(2) . . . . ?
N3 C9 C8 C7 -1.7(5) . . . . ?
N3 C11 C13 O5 175.0(2) . . . . ?
N3 C11 C13 O4 -6.3(4) . . . . ?
N3 C11 C10 N2 0.1(3) . . . . ?
N3 C11 C10 C12 -178.3(3) . . . . ?
N2 C9 C8 C7 176.7(2) . . . . ?
C19 C18 C17 C16 -0.7(4) . . . . ?
C19 C20 C21 C16 -0.7(4) . . . . ?
C24 N5 C25 C26 0.2(3) . . . . ?
C24 N5 C25 C27 -180.0(2) . . . . ?
C24 N6 C26 C25 -0.7(2) . . . . ?
C24 N6 C26 C28 175.4(2) . . . . ?
C24 C23 C22 C19 -179.10(19) . . . . ?
C22 C19 C18 C17 -178.43(19) . . . . ?
C22 C19 C20 C21 179.0(2) . . . . ?
C9 N3 C11 C13 177.5(2) . . . . ?
C9 N3 C11 C10 0.4(3) . . . . ?
C9 N2 C10 C11 -0.6(3) . . . . ?
C9 N2 C10 C12 178.0(2) . . . . ?
N1 C1 C2 C3 178.0(2) . . . . ?
N1 C1 C6 C5 -177.4(3) . . . . ?
C25 N5 C24 N6 -0.6(2) . . . . ?
C25 N5 C24 C23 -179.35(19) . . . . ?
C25 C26 C28 O9 171.2(3) . . . . ?
C25 C26 C28 O10 -9.3(4) . . . . ?
O6 N4 C16 C17 -7.3(4) . . . . ?
O6 N4 C16 C21 172.6(3) . . . . ?
N4 C16 C17 C18 -179.8(2) . . . . ?
N4 C16 C21 C20 -179.6(2) . . . . ?
O1 N1 C1 C2 -5.5(4) . . . . ?
O1 N1 C1 C6 172.8(3) . . . . ?
C11 N3 C9 N2 -0.7(3) . . . . ?
C11 N3 C9 C8 177.9(2) . . . . ?
C26 N6 C24 N5 0.9(2) . . . . ?
C26 N6 C24 C23 179.61(19) . . . . ?
C13 O5 C14 C15 -177.7(2) . . . . ?
C13 C11 C10 N2 -176.8(2) . . . . ?
C13 C11 C10 C12 4.8(5) . . . . ?
C4 C7 C8 C9 179.8(2) . . . . ?
C4 C3 C2 C1 -1.4(4) . . . . ?
C4 C5 C6 C1 0.3(4) . . . . ?
C10 N2 C9 N3 0.8(3) . . . . ?
C10 N2 C9 C8 -177.9(2) . . . . ?
C10 C11 C13 O5 -8.6(3) . . . . ?
C10 C11 C13 O4 170.1(3) . . . . ?
C18 C19 C22 C23 -178.8(2) . . . . ?
C18 C19 C20 C21 0.3(3) . . . . ?
C20 C19 C22 C23 2.4(4) . . . . ?
C20 C19 C18 C17 0.4(3) . . . . ?
C7 C4 C3 C2 -177.8(2) . . . . ?
C7 C4 C5 C6 178.3(3) . . . . ?
C17 C16 C21 C20 0.4(4) . . . . ?
C21 C16 C17 C18 0.3(4) . . . . ?
C28 O10 C29 C30 128.6(4) . . . . ?
C3 C4 C7 C8 5.3(4) . . . . ?
C3 C4 C5 C6 -2.0(4) . . . . ?
O2 N1 C1 C2 172.8(3) . . . . ?
O2 N1 C1 C6 -8.9(4) . . . . ?
C27 C25 C26 N6 -179.5(2) . . . . ?
C27 C25 C26 C28 4.7(4) . . . . ?
C14 O5 C13 O4 -0.1(4) . . . . ?
C14 O5 C13 C11 178.6(2) . . . . ?
O7 N4 C16 C17 175.5(3) . . . . ?
O7 N4 C16 C21 -4.5(4) . . . . ?
C2 C1 C6 C5 0.9(4) . . . . ?
C5 C4 C7 C8 -175.0(3) . . . . ?
C5 C4 C3 C2 2.6(4) . . . . ?
C6 C1 C2 C3 -0.3(4) . . . . ?
C29 O10 C28 O9 -5.9(5) . . . . ?
C29 O10 C28 C26 174.6(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.752
_oxdiff_exptl_absorpt_empirical_full_min 0.137
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4f
_database_code_depnum_ccdc_archive 'CCDC 2469649'
loop_
_audit_author_name
_audit_author_address
'Ivan A. Moskalev'
;Synchrotron Radiation Facility SKIF
Russia
;
_audit_update_record             
;
2025-07-03 deposited with the CCDC.	2025-10-20 downloaded from the CCDC.
;
_audit_creation_date             2025-05-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2017/1
loop_
_audit_author_email
i.a.moskalev@srf-skif.ru
_chemical_name_common            ?
_chemical_name_systematic        
1-(1-Methoxy-4-methyl-2-((E)-2-phenylethenyl)-1H-imidazol-5-yl)ethanone
_chemical_formula_moiety         'C15 H16 N2 O2'
_chemical_formula_sum            'C15 H16 N2 O2'
_chemical_formula_weight         256.30
_chemical_melting_point          385-387
_chemical_oxdiff_formula         'C11 H10 N O'
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.5492(8)
_cell_length_b                   7.7057(9)
_cell_length_c                   13.4133(14)
_cell_angle_alpha                96.792(9)
_cell_angle_beta                 99.738(9)
_cell_angle_gamma                114.016(11)
_cell_volume                     687.12(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1125
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      33.1240
_cell_measurement_theta_min      2.9460
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.929
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41290
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light gray'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    gray
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.9
_exptl_crystal_size_mid          0.64
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1131
_diffrn_reflns_av_unetI/netI     0.1122
_diffrn_reflns_Laue_measured_fraction_full 0.960
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7588
_diffrn_reflns_point_group_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        25.019
_diffrn_reflns_theta_max         25.019
_diffrn_reflns_theta_min         1.575
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -65.00 114.50   0.50   36.00    --   25.00   0.00  35.00  359
  2  ω    -65.00  54.50   0.50   36.00    --   25.00 -72.00  35.00  239
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'esperanto-CrysAlisPro-abstract goniometer imported esperanto images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0505784000
_diffrn_orient_matrix_UB_12      -0.0857075000
_diffrn_orient_matrix_UB_13      -0.0391981000
_diffrn_orient_matrix_UB_21      -0.0172002000
_diffrn_orient_matrix_UB_22      -0.0568452000
_diffrn_orient_matrix_UB_23      0.0383612000
_diffrn_orient_matrix_UB_31      -0.0914909000
_diffrn_orient_matrix_UB_32      0.0060188000
_diffrn_orient_matrix_UB_33      -0.0007572000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1846
_reflns_number_total             2317
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2317
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0909
_refine_ls_R_factor_gt           0.0773
_refine_ls_restrained_S_all      1.030
_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)+(0.0906P)²+0.1699P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2081
_refine_ls_wR_factor_ref         0.2239
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C3(H3), C5(H5), C6(H6), C1(H1), C2(H2)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.3928(3) 0.9310(3) 0.60098(14) 0.0659(6) Uani 1 1 d . . . . .
N1 N 0.3068(3) 0.7473(3) 0.62392(15) 0.0547(5) Uani 1 1 d . . . . .
N2 N 0.1903(3) 0.4301(3) 0.60075(16) 0.0585(6) Uani 1 1 d . . . . .
O2 O 0.3606(5) 1.0215(4) 0.80585(19) 0.1060(9) Uani 1 1 d . . . . .
C9 C 0.2612(3) 0.5822(4) 0.55631(19) 0.0535(6) Uani 1 1 d . . . . .
C10 C 0.2664(3) 0.7027(4) 0.71737(18) 0.0554(6) Uani 1 1 d . . . . .
C11 C 0.1933(3) 0.5022(4) 0.69925(19) 0.0558(6) Uani 1 1 d . . . . .
C4 C 0.2683(4) 0.3821(4) 0.28206(19) 0.0597(7) Uani 1 1 d . . . . .
C7 C 0.2557(4) 0.4130(4) 0.38956(19) 0.0608(7) Uani 1 1 d . . . . .
H7 H 0.223668 0.304824 0.419652 0.073 Uiso 1 1 calc R U . . .
C8 C 0.2845(4) 0.5776(4) 0.45021(19) 0.0611(7) Uani 1 1 d . . . . .
H8 H 0.319889 0.690867 0.424465 0.073 Uiso 1 1 calc R U . . .
C3 C 0.3346(4) 0.5313(5) 0.2281(2) 0.0689(7) Uani 1 1 d . . . . .
H3 H 0.377287 0.659309 0.261375 0.083 Uiso 1 1 calc R U . . .
C13 C 0.3017(4) 0.8510(4) 0.8088(2) 0.0661(7) Uani 1 1 d . . . . .
C5 C 0.2121(4) 0.1928(5) 0.2301(2) 0.0736(8) Uani 1 1 d . . . . .
H5 H 0.172354 0.091826 0.265367 0.088 Uiso 1 1 calc R U . . .
C14 C 0.2600(5) 0.7826(5) 0.9063(2) 0.0801(9) Uani 1 1 d . . . . .
H14A H 0.300532 0.892758 0.961198 0.120 Uiso 1 1 calc R U . . .
H14B H 0.333060 0.709450 0.924396 0.120 Uiso 1 1 calc R U . . .
H14C H 0.119560 0.701823 0.895503 0.120 Uiso 1 1 calc R U . . .
C15 C 0.1184(5) 0.3618(5) 0.7672(2) 0.0768(9) Uani 1 1 d . . . . .
H15A H 0.092606 0.234244 0.733105 0.115 Uiso 1 1 calc R U . . .
H15B H -0.002735 0.360479 0.781123 0.115 Uiso 1 1 calc R U . . .
H15C H 0.217165 0.400604 0.831107 0.115 Uiso 1 1 calc R U . . .
C6 C 0.2144(5) 0.1523(6) 0.1270(2) 0.0858(9) Uani 1 1 d . . . . .
H6 H 0.173931 0.024821 0.093476 0.103 Uiso 1 1 calc R U . . .
C12 C 0.2403(5) 0.9946(5) 0.5682(3) 0.0837(9) Uani 1 1 d . . . . .
H12A H 0.141112 0.900919 0.509897 0.126 Uiso 1 1 calc R U . . .
H12B H 0.300042 1.117947 0.548948 0.126 Uiso 1 1 calc R U . . .
H12C H 0.178788 1.007094 0.623940 0.126 Uiso 1 1 calc R U . . .
C1 C 0.2761(5) 0.2995(6) 0.0744(2) 0.0861(10) Uani 1 1 d . . . . .
H1 H 0.277308 0.272491 0.005177 0.103 Uiso 1 1 calc R U . . .
C2 C 0.3369(5) 0.4894(6) 0.1250(2) 0.0835(9) Uani 1 1 d . . . . .
H2 H 0.379744 0.589595 0.089412 0.100 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 N1 1.394(2) . ?
O1 C12 1.448(3) . ?
N1 C9 1.350(3) . ?
N1 C10 1.389(3) . ?
N2 C9 1.333(3) . ?
N2 C11 1.364(3) . ?
O2 C13 1.212(3) . ?
C9 C8 1.461(4) . ?
C10 C11 1.387(3) . ?
C10 C13 1.480(4) . ?
C11 C15 1.493(3) . ?
C4 C7 1.459(4) . ?
C4 C3 1.395(4) . ?
C4 C5 1.396(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.338(4) . ?
C8 H8 0.9300 . ?
C3 H3 0.9300 . ?
C3 C2 1.387(4) . ?
C13 C14 1.502(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.386(4) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C6 H6 0.9300 . ?
C6 C1 1.368(5) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C1 H1 0.9300 . ?
C1 C2 1.387(5) . ?
C2 H2 0.9300 . ?

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
N1 O1 C12 110.15(19) . . ?
C9 N1 O1 122.9(2) . . ?
C9 N1 C10 109.4(2) . . ?
C10 N1 O1 127.5(2) . . ?
C9 N2 C11 106.5(2) . . ?
N1 C9 C8 123.4(2) . . ?
N2 C9 N1 109.8(2) . . ?
N2 C9 C8 126.8(2) . . ?
N1 C10 C13 123.3(2) . . ?
C11 C10 N1 103.5(2) . . ?
C11 C10 C13 133.2(2) . . ?
N2 C11 C10 110.8(2) . . ?
N2 C11 C15 118.2(2) . . ?
C10 C11 C15 131.0(2) . . ?
C3 C4 C7 123.8(3) . . ?
C3 C4 C5 117.9(3) . . ?
C5 C4 C7 118.3(2) . . ?
C4 C7 H7 116.0 . . ?
C8 C7 C4 128.1(3) . . ?
C8 C7 H7 116.0 . . ?
C9 C8 H8 119.5 . . ?
C7 C8 C9 121.0(2) . . ?
C7 C8 H8 119.5 . . ?
C4 C3 H3 119.9 . . ?
C2 C3 C4 120.3(3) . . ?
C2 C3 H3 119.9 . . ?
O2 C13 C10 121.9(3) . . ?
O2 C13 C14 120.6(3) . . ?
C10 C13 C14 117.5(2) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 C4 121.4(3) . . ?
C6 C5 H5 119.3 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C11 C15 H15A 109.5 . . ?
C11 C15 H15B 109.5 . . ?
C11 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C5 C6 H6 120.0 . . ?
C1 C6 C5 120.1(3) . . ?
C1 C6 H6 120.0 . . ?
O1 C12 H12A 109.5 . . ?
O1 C12 H12B 109.5 . . ?
O1 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C6 C1 H1 120.2 . . ?
C6 C1 C2 119.6(3) . . ?
C2 C1 H1 120.2 . . ?
C3 C2 H2 119.7 . . ?
C1 C2 C3 120.7(3) . . ?
C1 C2 H2 119.7 . . ?

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 N1 C9 N2 176.94(18) . . . . ?
O1 N1 C9 C8 -4.2(4) . . . . ?
O1 N1 C10 C11 -176.6(2) . . . . ?
O1 N1 C10 C13 3.2(4) . . . . ?
N1 C9 C8 C7 173.4(2) . . . . ?
N1 C10 C11 N2 0.1(3) . . . . ?
N1 C10 C11 C15 -178.6(3) . . . . ?
N1 C10 C13 O2 3.4(4) . . . . ?
N1 C10 C13 C14 -177.2(2) . . . . ?
N2 C9 C8 C7 -8.0(4) . . . . ?
C9 N1 C10 C11 -0.5(2) . . . . ?
C9 N1 C10 C13 179.3(2) . . . . ?
C9 N2 C11 C10 0.2(3) . . . . ?
C9 N2 C11 C15 179.2(2) . . . . ?
C10 N1 C9 N2 0.6(3) . . . . ?
C10 N1 C9 C8 179.5(2) . . . . ?
C11 N2 C9 N1 -0.5(3) . . . . ?
C11 N2 C9 C8 -179.3(2) . . . . ?
C11 C10 C13 O2 -176.9(3) . . . . ?
C11 C10 C13 C14 2.5(4) . . . . ?
C4 C7 C8 C9 178.5(2) . . . . ?
C4 C3 C2 C1 -0.8(4) . . . . ?
C4 C5 C6 C1 1.2(5) . . . . ?
C7 C4 C3 C2 -178.2(2) . . . . ?
C7 C4 C5 C6 177.9(3) . . . . ?
C3 C4 C7 C8 6.9(4) . . . . ?
C3 C4 C5 C6 -2.4(4) . . . . ?
C13 C10 C11 N2 -179.6(2) . . . . ?
C13 C10 C11 C15 1.6(5) . . . . ?
C5 C4 C7 C8 -173.5(3) . . . . ?
C5 C4 C3 C2 2.2(4) . . . . ?
C5 C6 C1 C2 0.2(5) . . . . ?
C6 C1 C2 C3 -0.4(5) . . . . ?
C12 O1 N1 C9 97.6(3) . . . . ?
C12 O1 N1 C10 -86.8(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.268
_oxdiff_exptl_absorpt_empirical_full_min 0.315
