# Supplementary Information (SI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 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_ps_dok61a_twin1_hklf4
_database_code_depnum_ccdc_archive 'CCDC 2350542'
loop_
_audit_author_name
_audit_author_address
'Paulina Sobczak'
;Lodz University of Technology
Poland
;
_audit_update_record             
;
2024-04-23 deposited with the CCDC.	2025-01-10 downloaded from the CCDC.
;
_audit_creation_date             2023-12-07
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H11 N3 O4'
_chemical_formula_sum            'C12 H11 N3 O4'
_chemical_formula_weight         261.24
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C12 H11 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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   6.4229(3)
_cell_length_b                   7.1501(2)
_cell_length_c                   13.0240(4)
_cell_angle_alpha                74.165(2)
_cell_angle_beta                 84.153(3)
_cell_angle_gamma                86.204(3)
_cell_volume                     571.97(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9196
_cell_measurement_temperature    99.9(5)
_cell_measurement_theta_max      79.1130
_cell_measurement_theta_min      6.4780
_shelx_estimated_absorpt_T_max   0.967
_shelx_estimated_absorpt_T_min   0.741
_exptl_absorpt_coefficient_mu    0.986
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_correction_T_min  0.820
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.64a (Rigaku Oxford Diffraction, 2022)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             272
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
4 0 3 0.0277
-4 0 -3 0.0277
0 5 2 0.1736
1 0 8 0.0191
1 0 -8 0.0238
3 0 6 0.0293
-3 1 4 0.0410
-1 0 -8 0.0132
0 -5 -2 0.1478
1 -4 -1 0.1368
3 3 3 0.1114
1 1 -7 0.0249
3 0 -4 0.0242
-2 0 6 0.0352

_exptl_crystal_size_max          0.324
_exptl_crystal_size_mid          0.066
_exptl_crystal_size_min          0.034
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
4.0500 0.0758 2.6118 -0.0244 -0.1092 0.9937
-4.0500 -0.0758 -2.6118 0.0244 0.1092 -0.9937
0.1538 4.6181 1.5014 -0.2305 -0.9621 -0.1458
0.9095 0.1606 8.1388 0.8739 -0.2083 0.4391
1.1333 -0.4205 -7.7584 -0.9714 0.2325 0.0490
3.2026 -0.2357 5.5534 0.4178 -0.0984 0.9032
-3.4708 0.6004 3.9317 0.6925 -0.1669 -0.7019
-1.1651 -0.1229 -8.0378 -0.8446 0.2012 -0.4961
-0.3450 -4.6240 -1.6254 0.2317 0.9677 0.0990
1.2036 -4.2779 -0.5304 0.2066 0.8601 0.4663
3.1213 3.2618 2.9678 -0.1803 -0.7487 0.6379
1.4887 0.5177 -7.0282 -0.9941 0.0251 0.1056
3.4423 0.1388 -3.9115 -0.7511 0.0180 0.6600
-2.2792 -0.4005 6.1882 0.9486 -0.0236 -0.3157

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0059
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            2527
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.760
_diffrn_reflns_theta_min         3.541
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(5)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 300K'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -43.00  27.00   0.50    1.00    --  -48.87  38.00 -90.00  140
  2  ω   -125.00 -35.00   0.50    1.00    --  -48.87 -19.00 -30.00  180
  3  ω    -72.00  17.00   0.50    1.00    --  -48.87  77.00 150.00  178
  4  ω    -43.00  27.00   0.50    1.00    --  -48.87  38.00 -60.00  140
  5  ω    -27.00  26.00   0.50    1.00    --   48.87 -19.00-150.00  106
  6  ω    -43.00 -13.00   0.50    3.00    --  -88.50  38.00  30.00   60
  7  ω    -43.00 -13.00   0.50    3.00    --  -88.50  38.00 120.00   60
  8  ω   -160.00 -73.00   0.50    3.00    --  -88.50 -57.00 -90.00  174
  9  ω    -43.00 -13.00   0.50    3.00    --  -88.50  38.00 -90.00   60
 10  ω   -154.00 -65.00   0.50    3.00    --  -88.50 -77.00 -30.00  178
 11  ω   -158.00 -73.00   0.50    3.00    --  -88.50-125.00 -90.00  170
 12  ω    -87.00 -19.00   0.50    3.00    --  -88.50 125.00 120.00  136
 13  ω    -66.00 -17.00   0.50    3.00    --  -88.50  57.00   0.00   98
 14  ω    -43.00 -13.00   0.50    3.00    --  -88.50  38.00  60.00   60
 15  ω    -87.00 -19.00   0.50    3.00    --  -88.50 125.00-120.00  136
 16  ω     38.00  66.00   0.50    3.00    --  110.00 -57.00   0.00   56
 17  ω     41.00 106.00   0.50    3.00    --  110.00 -99.00 -90.00  130
 18  ω     38.00  66.00   0.50    3.00    --  110.00 -57.00-180.00   56
 19  ω     94.00 178.00   0.50    3.00    --  110.00  57.00  90.00  168
 20  ω     41.00 106.00   0.50    3.00    --  110.00 -99.00  30.00  130
 21  ω     38.00  66.00   0.50    3.00    --  110.00 -57.00-150.00   56
 22  ω     38.00  66.00   0.50    3.00    --  110.00 -57.00 150.00   56
 23  ω     97.00 178.00   0.50    3.00    --  110.00  19.00-180.00  162
 24  ω     45.00 105.00   0.50    3.00    --  110.00 -77.00  30.00  120
 25  ω     38.00  66.00   0.50    3.00    --  110.00 -57.00 -60.00   56
 26  ω     41.00 113.00   0.50    3.00    --  110.00-125.00  30.00  144
 27  ω     41.00 113.00   0.50    3.00    --  110.00-125.00-180.00  144
 28  ω     45.00 105.00   0.50    3.00    --  110.00 -77.00  60.00  120
 29  ω     41.00 106.00   0.50    3.00    --  110.00 -99.00-150.00  130
 30  ω   -114.00 -25.00   0.50    1.00    --  -48.87 -77.00-180.00  178
 31  ω   -114.00 -25.00   0.50    1.00    --  -48.87 -77.00 -60.00  178
 32  ω     33.00 121.00   0.50    1.00    --   48.87  57.00 150.00  176
 33  ω     25.00 114.00   0.50    1.00    --   48.87  77.00  60.00  178
 34  ω     25.00 114.00   0.50    1.00    --   48.87  77.00-150.00  178
 35  ω   -154.00 -65.00   0.50    3.00    --  -88.50 -77.00  90.00  178
 36  ω   -154.00 -65.00   0.50    3.00    --  -88.50 -77.00   0.00  178
 37  ω   -154.00 -65.00   0.50    3.00    --  -88.50 -77.00  30.00  178
 38  ω   -160.00 -73.00   0.50    3.00    --  -88.50 -57.00 120.00  174
 39  ω    -43.00 -13.00   0.50    3.00    --  -88.50  38.00-120.00   60
 40  ω   -160.00 -73.00   0.50    3.00    --  -88.50 -57.00-120.00  174
 41  ω   -154.00 -65.00   0.50    3.00    --  -88.50 -77.00-150.00  178
 42  ω   -154.00 -65.00   0.50    3.00    --  -88.50 -77.00 -60.00  178
 43  ω   -154.00 -65.00   0.50    3.00    --  -88.50 -77.00 -90.00  178
 44  ω   -154.00 -65.00   0.50    3.00    --  -88.50 -77.00  60.00  178
 45  ω   -157.00 -85.00   0.50    3.00    --  -88.50 -99.00 -30.00  144
 46  ω   -154.00 -65.00   0.50    3.00    --  -88.50 -77.00 150.00  178
 47  ω   -154.00 -65.00   0.50    3.00    --  -88.50 -77.00-120.00  178
 48  ω   -160.00 -73.00   0.50    3.00    --  -88.50 -57.00  30.00  174
 49  ω   -164.00 -75.00   0.50    3.00    --  -88.50 -19.00  60.00  178
 50  ω   -154.00 -65.00   0.50    3.00    --  -88.50 -77.00 120.00  178
 51  ω   -154.00 -65.00   0.50    3.00    --  -88.50 -77.00-180.00  178
 52  ω   -160.00 -73.00   0.50    3.00    --  -88.50 -57.00 -60.00  174
 53  ω     97.00 178.00   0.50    3.00    --  110.00  19.00 -30.00  162
 54  ω     45.00 105.00   0.50    3.00    --  110.00 -77.00 -90.00  120
 55  ω     25.00 114.00   0.50    1.00    --   48.87  77.00 -90.00  178
 56  ω     25.00 114.00   0.50    1.00    --   48.87  77.00 -30.00  178
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0805703000
_diffrn_orient_matrix_UB_12      -0.0856048000
_diffrn_orient_matrix_UB_13      0.1180720000
_diffrn_orient_matrix_UB_21      -0.0099731000
_diffrn_orient_matrix_UB_22      -0.2013319000
_diffrn_orient_matrix_UB_23      -0.0205116000
_diffrn_orient_matrix_UB_31      0.2272352000
_diffrn_orient_matrix_UB_32      -0.0487386000
_diffrn_orient_matrix_UB_33      0.0295221000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2342
_reflns_number_total             2527
_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.64a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.64a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.64a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2527
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0377
_refine_ls_restrained_S_all      1.115
_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)+(0.0764P)²+0.1092P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1186
_refine_ls_wR_factor_ref         0.1211
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.590(3)
 0.410(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C3(H3), C4(H4), C8(H8), C10(H10), C11(H11)
3.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_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
C5 C 0.7030(2) 0.80793(17) 0.32721(10) 0.0151(3) Uani 1 1 d . . . . .
C6 C 0.7373(2) 0.87555(18) 0.21609(10) 0.0161(3) Uani 1 1 d . . . . .
H6 H 0.629195 0.948272 0.176009 0.019 Uiso 1 1 calc R U . . .
C7 C 0.9280(2) 0.83760(18) 0.16337(10) 0.0161(3) Uani 1 1 d . . . . .
H7 H 0.949805 0.883930 0.087609 0.019 Uiso 1 1 calc R U . . .
C2 C 1.0872(2) 0.73154(18) 0.22181(10) 0.0163(3) Uani 1 1 d . . . . .
C3 C 1.0533(2) 0.66585(18) 0.33326(10) 0.0167(3) Uani 1 1 d . . . . .
H3 H 1.161956 0.594370 0.373407 0.020 Uiso 1 1 calc R U . . .
C4 C 0.8635(2) 0.70362(18) 0.38593(10) 0.0174(3) Uani 1 1 d . . . . .
H4 H 0.842453 0.658726 0.461775 0.021 Uiso 1 1 calc R U . . .
O1 O 1.27898(14) 0.68212(14) 0.17775(7) 0.0203(2) Uani 1 1 d . . . . .
C1 C 1.3240(2) 0.7630(2) 0.06518(10) 0.0228(3) Uani 1 1 d . . . . .
H1A H 1.223893 0.717174 0.026402 0.034 Uiso 1 1 calc R U . . .
H1B H 1.466520 0.721941 0.043492 0.034 Uiso 1 1 calc R U . . .
H1C H 1.312610 0.905269 0.048428 0.034 Uiso 1 1 calc R U . . .
N1 N 0.50696(18) 0.84724(16) 0.37624(8) 0.0171(3) Uani 1 1 d . . . . .
H1 H 0.414(3) 0.925(2) 0.3367(13) 0.021 Uiso 1 1 d . U . . .
N2 N 0.46275(17) 0.77799(15) 0.48172(8) 0.0162(3) Uani 1 1 d . . . . .
C8 C 0.2806(2) 0.82662(18) 0.52170(10) 0.0167(3) Uani 1 1 d . . . . .
H8 H 0.183639 0.908169 0.477413 0.020 Uiso 1 1 calc R U . . .
C9 C 0.23043(19) 0.75352(18) 0.63470(10) 0.0155(3) Uani 1 1 d . . . . .
C10 C 0.3386(2) 0.63916(18) 0.71690(9) 0.0166(3) Uani 1 1 d . . . . .
H10 H 0.476832 0.584848 0.710793 0.020 Uiso 1 1 calc R U . . .
C11 C 0.2055(2) 0.61813(18) 0.81145(9) 0.0168(3) Uani 1 1 d . . . . .
H11 H 0.234831 0.547167 0.881870 0.020 Uiso 1 1 calc R U . . .
C12 C 0.0252(2) 0.72106(18) 0.78092(9) 0.0150(3) Uani 1 1 d . . . . .
O2 O 0.03445(14) 0.80485(13) 0.67354(7) 0.0152(2) Uani 1 1 d . . . . .
N3 N -0.15774(17) 0.75482(15) 0.84178(8) 0.0164(3) Uani 1 1 d . . . . .
O3 O -0.16193(16) 0.68687(14) 0.94066(7) 0.0226(2) Uani 1 1 d . . . . .
O4 O -0.30675(14) 0.85071(14) 0.79651(7) 0.0214(2) Uani 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
C5 C6 1.3942(17) . ?
C5 C4 1.3971(19) . ?
C5 N1 1.3996(16) . ?
C6 H6 0.9500 . ?
C6 C7 1.3902(17) . ?
C7 H7 0.9500 . ?
C7 C2 1.3929(18) . ?
C2 C3 1.3971(17) . ?
C2 O1 1.3715(15) . ?
C3 H3 0.9500 . ?
C3 C4 1.3848(18) . ?
C4 H4 0.9500 . ?
O1 C1 1.4284(15) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
N1 H1 0.892(18) . ?
N1 N2 1.3346(15) . ?
N2 C8 1.2965(17) . ?
C8 H8 0.9500 . ?
C8 C9 1.4314(17) . ?
C9 C10 1.3769(18) . ?
C9 O2 1.3731(15) . ?
C10 H10 0.9500 . ?
C10 C11 1.4040(17) . ?
C11 H11 0.9500 . ?
C11 C12 1.3644(18) . ?
C12 O2 1.3598(14) . ?
C12 N3 1.3946(16) . ?
N3 O3 1.2444(14) . ?
N3 O4 1.2414(14) . ?

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
C6 C5 C4 119.45(12) . . ?
C6 C5 N1 118.41(11) . . ?
C4 C5 N1 122.14(11) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 C5 120.65(12) . . ?
C7 C6 H6 119.7 . . ?
C6 C7 H7 120.1 . . ?
C6 C7 C2 119.89(11) . . ?
C2 C7 H7 120.1 . . ?
C7 C2 C3 119.37(11) . . ?
O1 C2 C7 124.64(11) . . ?
O1 C2 C3 115.98(11) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.83(12) . . ?
C4 C3 H3 119.6 . . ?
C5 C4 H4 120.1 . . ?
C3 C4 C5 119.80(11) . . ?
C3 C4 H4 120.1 . . ?
C2 O1 C1 116.82(10) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C5 N1 H1 119.1(10) . . ?
N2 N1 C5 120.78(11) . . ?
N2 N1 H1 120.0(11) . . ?
C8 N2 N1 117.10(11) . . ?
N2 C8 H8 121.1 . . ?
N2 C8 C9 117.88(11) . . ?
C9 C8 H8 121.1 . . ?
C10 C9 C8 133.64(12) . . ?
O2 C9 C8 116.09(11) . . ?
O2 C9 C10 110.27(11) . . ?
C9 C10 H10 126.5 . . ?
C9 C10 C11 106.91(12) . . ?
C11 C10 H10 126.5 . . ?
C10 C11 H11 127.2 . . ?
C12 C11 C10 105.50(11) . . ?
C12 C11 H11 127.2 . . ?
C11 C12 N3 130.46(11) . . ?
O2 C12 C11 112.24(11) . . ?
O2 C12 N3 117.29(11) . . ?
C12 O2 C9 105.07(10) . . ?
O3 N3 C12 117.30(11) . . ?
O4 N3 C12 119.68(10) . . ?
O4 N3 O3 123.02(10) . . ?

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
C5 C6 C7 C2 -0.19(19) . . . . ?
C5 N1 N2 C8 177.54(11) . . . . ?
C6 C5 C4 C3 -1.02(19) . . . . ?
C6 C5 N1 N2 176.81(10) . . . . ?
C6 C7 C2 C3 -0.55(18) . . . . ?
C6 C7 C2 O1 178.39(11) . . . . ?
C7 C2 C3 C4 0.50(19) . . . . ?
C7 C2 O1 C1 6.71(18) . . . . ?
C2 C3 C4 C5 0.3(2) . . . . ?
C3 C2 O1 C1 -174.32(11) . . . . ?
C4 C5 C6 C7 0.98(19) . . . . ?
C4 C5 N1 N2 -3.09(19) . . . . ?
O1 C2 C3 C4 -178.52(10) . . . . ?
N1 C5 C6 C7 -178.93(11) . . . . ?
N1 C5 C4 C3 178.89(11) . . . . ?
N1 N2 C8 C9 179.94(10) . . . . ?
N2 C8 C9 C10 1.6(2) . . . . ?
N2 C8 C9 O2 -178.63(10) . . . . ?
C8 C9 C10 C11 179.54(13) . . . . ?
C8 C9 O2 C12 -179.39(10) . . . . ?
C9 C10 C11 C12 -0.09(14) . . . . ?
C10 C9 O2 C12 0.41(14) . . . . ?
C10 C11 C12 O2 0.36(14) . . . . ?
C10 C11 C12 N3 -178.10(13) . . . . ?
C11 C12 O2 C9 -0.48(14) . . . . ?
C11 C12 N3 O3 2.1(2) . . . . ?
C11 C12 N3 O4 -178.40(12) . . . . ?
O2 C9 C10 C11 -0.20(14) . . . . ?
O2 C12 N3 O3 -176.25(10) . . . . ?
O2 C12 N3 O4 3.21(17) . . . . ?
N3 C12 O2 C9 178.21(10) . . . . ?

_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 2.107
_oxdiff_exptl_absorpt_empirical_full_min 0.468
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.590(3) 15145 2402 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000
0.0000 1.0000
2 0.410(3) 0 2402 nmt -0.9994 0.1190 0.0001 -0.0001 0.9997 0.0013 -0.0018
1.0000 -0.9996

_twin_special_details            
;
Component 2 rotated by 179.9506° 
around [0.05 0.89 0.45] (reciprocal) or [-0.00 1.00 0.00] (direct)
;
####################################################################### 
# 
# 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_ps_dok65
_database_code_depnum_ccdc_archive 'CCDC 2350550'
loop_
_audit_author_name
_audit_author_address
'Paulina Sobczak'
;Lodz University of Technology
Poland
;
_audit_update_record             
;
2024-04-23 deposited with the CCDC.	2025-01-10 downloaded from the CCDC.
;
_audit_creation_date             2024-03-15
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H16 N2 O2'
_chemical_formula_sum            'C15 H16 N2 O2'
_chemical_formula_weight         256.30
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C15 H16 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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.19160(10)
_cell_length_b                   8.53580(10)
_cell_length_c                   29.4619(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1305.59(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9009
_cell_measurement_temperature    99.9(5)
_cell_measurement_theta_max      78.9650
_cell_measurement_theta_min      5.3680
_shelx_estimated_absorpt_T_max   0.964
_shelx_estimated_absorpt_T_min   0.859
_exptl_absorpt_coefficient_mu    0.709
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_correction_T_min  0.908
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.64a (Rigaku Oxford Diffraction, 2022)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             544
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 5 -3 0.0337
3 0 3 0.0861
-3 0 -3 0.1230
1 0 -19 0.0326
-1 0 19 0.0326
0 4 12 0.0262
0 -5 -9 0.0443
0 -5 6 0.0386
-1 5 -4 0.0387
-1 -5 2 0.0421
1 1 17 0.0532
0 -5 4 0.0362
-1 4 -13 0.0290
-1 0 -17 0.0494
-1 -5 -5 0.0484
0 0 -19 0.0200
0 0 19 0.0308

_exptl_crystal_size_max          0.221
_exptl_crystal_size_mid          0.085
_exptl_crystal_size_min          0.052
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.1836 5.4456 -3.3724 0.0398 0.1734 -0.9840
3.3229 0.1921 3.0995 -0.2309 -0.9642 -0.1303
-3.3216 0.0076 -3.2153 0.2318 0.9682 0.0940
0.6142 -0.0556 -18.8048 -0.9608 0.2302 -0.1545
-0.6142 0.0556 18.8048 0.9608 -0.2302 0.1545
-0.1336 4.3756 11.7113 0.7114 -0.1690 -0.6821
0.0013 -4.9396 -8.6672 -0.5708 0.1351 0.8099
-0.4888 -5.2207 5.7726 0.1585 -0.0397 0.9866
-0.9776 5.1794 -3.9223 0.0968 0.3977 -0.9124
-0.7500 -5.3561 2.4174 0.0258 0.1007 0.9946
1.4966 0.5723 17.0220 0.6498 -0.7596 -0.0266
-0.2989 -5.3998 3.9345 0.0439 -0.0541 0.9976
-0.6583 3.8618 -13.1954 -0.4211 0.4943 -0.7605
-1.4827 -0.3781 -17.1255 -0.6500 0.7599 -0.0091
-1.0158 -5.0766 -5.0481 -0.2870 0.3331 0.8982
-0.0966 -0.2096 -19.1047 -0.8980 0.4277 -0.1039
0.0715 -0.1204 19.1173 0.8907 -0.4243 0.1634

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            13101
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.116
_diffrn_reflns_theta_min         5.396
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(5)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 300K'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     97.00 178.00   0.50    1.00    --  110.00  19.00 120.00  162
  2  ω     25.00 114.00   0.50    0.20    --   48.87  77.00   0.00  178
  3  ω     25.00 114.00   0.50    0.20    --   48.87  77.00-120.00  178
  4  ω    -43.00 -13.00   0.50    1.00    --  -88.50  38.00 120.00   60
  5  ω    -43.00 -13.00   0.50    1.00    --  -88.50  38.00  90.00   60
  6  ω    -43.00 -13.00   0.50    1.00    --  -88.50  38.00 -30.00   60
  7  ω    -66.00 -17.00   0.50    1.00    --  -88.50  57.00 -60.00   98
  8  ω   -108.00 -28.00   0.50    1.00    --  -88.50 156.00  85.00  160
  9  ω   -114.00 -25.00   0.50    0.20    --  -48.87 -77.00  90.00  178
 10  ω   -160.00 -73.00   0.50    1.00    --  -88.50 -57.00  60.00  174
 11  ω   -154.00-119.00   0.50    1.00    --  -88.50 -77.00 -30.00   70
 12  ω   -114.00 -25.00   0.50    0.20    --  -48.87 -77.00-180.00  178
 13  ω    -27.00  24.00   0.50    0.20    --   48.87 -14.00 -69.00  102
 14  ω     45.00 105.00   0.50    1.00    --  110.00 -77.00-180.00  120
 15  ω     38.00  66.00   0.50    1.00    --  110.00 -57.00 -90.00   56
 16  ω     38.00  66.00   0.50    1.00    --  110.00 -57.00 -30.00   56
 17  ω     38.00  66.00   0.50    1.00    --  110.00 -57.00   0.00   56
 18  ω     38.00  66.00   0.50    1.00    --  110.00 -57.00  30.00   56
 19  ω     38.00  66.00   0.50    1.00    --  110.00 -57.00 120.00   56
 20  ω     41.00 113.00   0.50    1.00    --  110.00-125.00-120.00  144
 21  ω     41.00 113.00   0.50    1.00    --  110.00-125.00 -60.00  144
 22  ω    -43.00  27.00   0.50    0.20    --  -48.87  38.00 150.00  140
 23  ω    -24.00  27.00   0.50    0.20    --  -48.87  14.00 101.00  102
 24  ω    -26.00  27.00   0.50    0.20    --  -48.87  19.00  30.00  106
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1154356000
_diffrn_orient_matrix_UB_12      0.0326632000
_diffrn_orient_matrix_UB_13      0.0472272000
_diffrn_orient_matrix_UB_21      -0.2710243000
_diffrn_orient_matrix_UB_22      0.0096242000
_diffrn_orient_matrix_UB_23      -0.0211198000
_diffrn_orient_matrix_UB_31      -0.0360279000
_diffrn_orient_matrix_UB_32      -0.1772352000
_diffrn_orient_matrix_UB_33      0.0075633000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.635
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.912
_reflns_number_gt                2564
_reflns_number_total             2692
_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 1.171.42.64a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.64a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.64a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    
'olex2.solve 1.5-ac5-024 (Bourhis et al., 2015)'
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 
;
 Flack x determined using 979 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2692
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0286
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0375P)²+0.2148P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0734
_refine_ls_wR_factor_ref         0.0746
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C3(H3), C4(H4), C8(H8), C14(H14), C13(H13), C11(H11), C10(H10)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
C5 C 0.8257(3) 0.77728(18) 0.75207(5) 0.0239(3) Uani 1 1 d . . . . .
C6 C 0.8588(3) 0.86414(19) 0.79185(6) 0.0267(3) Uani 1 1 d . . . . .
H6 H 0.992868 0.939631 0.793570 0.032 Uiso 1 1 calc R U . . .
C7 C 0.6987(3) 0.84145(19) 0.82868(6) 0.0267(3) Uani 1 1 d . . . . .
H7 H 0.722283 0.902247 0.855366 0.032 Uiso 1 1 calc R U . . .
C2 C 0.5029(3) 0.73009(19) 0.82700(6) 0.0248(3) Uani 1 1 d . . . . .
C3 C 0.4670(3) 0.64319(19) 0.78744(5) 0.0253(3) Uani 1 1 d . . . . .
H3 H 0.333591 0.567221 0.785907 0.030 Uiso 1 1 calc R U . . .
C4 C 0.6268(3) 0.66777(18) 0.75022(5) 0.0252(3) Uani 1 1 d . . . . .
H4 H 0.599964 0.609232 0.723202 0.030 Uiso 1 1 calc R U . . .
O1 O 0.3575(2) 0.71502(14) 0.86567(4) 0.0304(3) Uani 1 1 d . . . . .
C1 C 0.1926(3) 0.5822(2) 0.86836(6) 0.0308(4) Uani 1 1 d . . . . .
H1A H 0.053195 0.592829 0.846153 0.046 Uiso 1 1 calc R U . . .
H1B H 0.119463 0.575124 0.898954 0.046 Uiso 1 1 calc R U . . .
H1C H 0.291706 0.487086 0.861823 0.046 Uiso 1 1 calc R U . . .
N1 N 0.9918(3) 0.80698(17) 0.71501(5) 0.0307(3) Uani 1 1 d . . . . .
H1 H 1.153(4) 0.871(2) 0.7206(7) 0.037 Uiso 1 1 d . U . . .
N2 N 0.9581(3) 0.72982(15) 0.67574(5) 0.0251(3) Uani 1 1 d . . . . .
C8 C 1.1274(3) 0.75106(18) 0.64372(5) 0.0244(3) Uani 1 1 d . . . . .
H8 H 1.269801 0.818729 0.648782 0.029 Uiso 1 1 calc R U . . .
C9 C 1.1002(3) 0.67232(18) 0.60046(5) 0.0239(3) Uani 1 1 d . . . . .
C14 C 1.2743(3) 0.70364(19) 0.56535(6) 0.0264(3) Uani 1 1 d . . . . .
H14 H 1.409275 0.776976 0.570083 0.032 Uiso 1 1 calc R U . . .
C13 C 1.2522(3) 0.62909(19) 0.52381(6) 0.0269(4) Uani 1 1 d . . . . .
H13 H 1.370983 0.651932 0.500188 0.032 Uiso 1 1 calc R U . . .
C12 C 1.0563(3) 0.52076(18) 0.51662(5) 0.0242(3) Uani 1 1 d . . . . .
C11 C 0.8831(3) 0.48672(19) 0.55135(5) 0.0262(3) Uani 1 1 d . . . . .
H11 H 0.750368 0.411778 0.546702 0.031 Uiso 1 1 calc R U . . .
C10 C 0.9053(3) 0.56274(19) 0.59272(5) 0.0255(3) Uani 1 1 d . . . . .
H10 H 0.785909 0.539910 0.616233 0.031 Uiso 1 1 calc R U . . .
O2 O 1.0508(2) 0.45341(14) 0.47423(4) 0.0284(3) Uani 1 1 d . . . . .
C15 C 0.8359(4) 0.3552(2) 0.46418(6) 0.0330(4) Uani 1 1 d . . . . .
H15A H 0.846812 0.319768 0.432595 0.050 Uiso 1 1 calc R U . . .
H15B H 0.675888 0.414204 0.468578 0.050 Uiso 1 1 calc R U . . .
H15C H 0.837333 0.264171 0.484443 0.050 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
C5 C6 1.397(2) . ?
C5 C4 1.394(2) . ?
C5 N1 1.414(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.380(2) . ?
C7 H7 0.9500 . ?
C7 C2 1.393(2) . ?
C2 C3 1.394(2) . ?
C2 O1 1.373(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.391(2) . ?
C4 H4 0.9500 . ?
O1 C1 1.423(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
N1 H1 1.01(2) . ?
N1 N2 1.343(2) . ?
N2 C8 1.302(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.448(2) . ?
C9 C14 1.400(2) . ?
C9 C10 1.396(2) . ?
C14 H14 0.9500 . ?
C14 C13 1.384(2) . ?
C13 H13 0.9500 . ?
C13 C12 1.391(2) . ?
C12 C11 1.393(2) . ?
C12 O2 1.375(2) . ?
C11 H11 0.9500 . ?
C11 C10 1.386(2) . ?
C10 H10 0.9500 . ?
O2 C15 1.426(2) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

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
C6 C5 N1 118.52(14) . . ?
C4 C5 C6 118.66(15) . . ?
C4 C5 N1 122.80(15) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 C5 120.72(15) . . ?
C7 C6 H6 119.6 . . ?
C6 C7 H7 119.8 . . ?
C6 C7 C2 120.48(15) . . ?
C2 C7 H7 119.8 . . ?
C7 C2 C3 119.37(15) . . ?
O1 C2 C7 115.83(14) . . ?
O1 C2 C3 124.80(15) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 119.95(14) . . ?
C4 C3 H3 120.0 . . ?
C5 C4 H4 119.6 . . ?
C3 C4 C5 120.80(14) . . ?
C3 C4 H4 119.6 . . ?
C2 O1 C1 116.85(13) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C5 N1 H1 118.4(12) . . ?
N2 N1 C5 119.85(14) . . ?
N2 N1 H1 120.8(12) . . ?
C8 N2 N1 117.90(14) . . ?
N2 C8 H8 119.8 . . ?
N2 C8 C9 120.48(14) . . ?
C9 C8 H8 119.8 . . ?
C14 C9 C8 119.93(14) . . ?
C10 C9 C8 121.71(14) . . ?
C10 C9 C14 118.35(15) . . ?
C9 C14 H14 119.6 . . ?
C13 C14 C9 120.82(15) . . ?
C13 C14 H14 119.6 . . ?
C14 C13 H13 120.0 . . ?
C14 C13 C12 120.05(15) . . ?
C12 C13 H13 120.0 . . ?
C13 C12 C11 119.93(15) . . ?
O2 C12 C13 115.56(14) . . ?
O2 C12 C11 124.50(15) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 C12 119.64(15) . . ?
C10 C11 H11 120.2 . . ?
C9 C10 H10 119.4 . . ?
C11 C10 C9 121.20(15) . . ?
C11 C10 H10 119.4 . . ?
C12 O2 C15 116.79(13) . . ?
O2 C15 H15A 109.5 . . ?
O2 C15 H15B 109.5 . . ?
O2 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
C5 C6 C7 C2 0.7(2) . . . . ?
C5 N1 N2 C8 -174.55(14) . . . . ?
C6 C5 C4 C3 -1.1(2) . . . . ?
C6 C5 N1 N2 -177.34(14) . . . . ?
C6 C7 C2 C3 -1.0(2) . . . . ?
C6 C7 C2 O1 178.96(14) . . . . ?
C7 C2 C3 C4 0.2(2) . . . . ?
C7 C2 O1 C1 -167.59(14) . . . . ?
C2 C3 C4 C5 0.9(2) . . . . ?
C3 C2 O1 C1 12.4(2) . . . . ?
C4 C5 C6 C7 0.4(2) . . . . ?
C4 C5 N1 N2 1.1(2) . . . . ?
O1 C2 C3 C4 -179.75(15) . . . . ?
N1 C5 C6 C7 178.86(15) . . . . ?
N1 C5 C4 C3 -179.59(15) . . . . ?
N1 N2 C8 C9 -179.40(14) . . . . ?
N2 C8 C9 C14 175.99(15) . . . . ?
N2 C8 C9 C10 -5.0(2) . . . . ?
C8 C9 C14 C13 179.72(14) . . . . ?
C8 C9 C10 C11 -179.21(15) . . . . ?
C9 C14 C13 C12 -0.4(2) . . . . ?
C14 C9 C10 C11 -0.2(2) . . . . ?
C14 C13 C12 C11 -0.3(2) . . . . ?
C14 C13 C12 O2 179.92(14) . . . . ?
C13 C12 C11 C10 0.8(2) . . . . ?
C13 C12 O2 C15 -173.26(14) . . . . ?
C12 C11 C10 C9 -0.6(2) . . . . ?
C11 C12 O2 C15 7.0(2) . . . . ?
C10 C9 C14 C13 0.7(2) . . . . ?
O2 C12 C11 C10 -179.46(14) . . . . ?

_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 1.526
_oxdiff_exptl_absorpt_empirical_full_min 0.641
####################################################################### 
# 
# 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_ps_dok59
_database_code_depnum_ccdc_archive 'CCDC 2350544'
loop_
_audit_author_name
_audit_author_address
'Paulina Sobczak'
;Lodz University of Technology
Poland
;
_audit_update_record             
;
2024-04-23 deposited with the CCDC.	2025-01-10 downloaded from the CCDC.
;
_audit_creation_date             2023-12-07
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H14 N2 O2'
_chemical_formula_sum            'C14 H14 N2 O2'
_chemical_formula_weight         242.27
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C14 H14 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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   26.7493(5)
_cell_length_b                   5.80660(10)
_cell_length_c                   7.7294(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.511(2)
_cell_angle_gamma                90
_cell_volume                     1195.00(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7990
_cell_measurement_temperature    99.9(5)
_cell_measurement_theta_max      78.8700
_cell_measurement_theta_min      4.9560
_shelx_estimated_absorpt_T_max   0.961
_shelx_estimated_absorpt_T_min   0.880
_exptl_absorpt_coefficient_mu    0.744
_exptl_absorpt_correction_T_max  0.956
_exptl_absorpt_correction_T_min  0.889
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.96a (Rigaku Oxford Diffraction, 2023)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             512
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
7 1 4 0.0522
5 3 2 0.0568
-15 2 2 0.0383
15 0 -3 0.0477
-15 -1 3 0.0484
-10 3 0 0.0608
4 3 -2 0.0842
12 -3 -1 0.0693
-1 -3 2 0.0985
-7 0 -4 0.0383
-7 -2 -3 0.0535
6 -1 4 0.0672
17 0 0 0.0352
-17 0 0 0.0171

_exptl_crystal_size_max          0.176
_exptl_crystal_size_mid          0.126
_exptl_crystal_size_min          0.054
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
7.3709 0.6708 4.2288 -0.2287 -0.9546 -0.1910
5.4944 3.2029 1.9553 -0.1831 -0.7698 0.6114
-14.6981 1.8180 1.5349 -0.8963 0.2138 0.3885
15.1494 0.3016 -2.8277 0.9469 -0.2270 0.2279
-14.5450 -0.7175 2.9600 -0.9136 0.2192 -0.3424
-10.3822 3.0176 0.0916 -0.6147 0.1457 0.7751
3.7168 3.2105 -2.4898 0.2655 -0.0652 0.9619
12.1197 -2.6929 -0.5820 0.7264 -0.1726 -0.6652
-1.0796 -3.4075 2.1405 -0.1034 0.0265 -0.9943
-7.0624 0.0989 -4.3639 0.2138 0.8963 0.3886
-6.7177 -2.4801 -3.0411 0.2189 0.9123 -0.3460
5.9083 -1.3293 4.1882 -0.1713 -0.7208 -0.6716
17.3016 0.1802 -0.1291 0.7258 -0.6877 -0.0179
-17.3033 -0.0809 0.0752 -0.7252 0.6870 0.0464

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_unetI/netI     0.0189
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.932
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            12265
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.932
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.447
_diffrn_reflns_theta_min         4.983
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(5)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 300K'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.932
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -119.00 -72.00   0.50    0.20    --  -48.87-126.00 -82.00   94
  2  ω   -120.00 -33.00   0.50    0.20    --  -48.87 -57.00 -60.00  174
  3  ω    -26.00  27.00   0.50    0.20    --  -48.87  19.00 -60.00  106
  4  ω    -26.00  27.00   0.50    0.20    --  -48.87  19.00 -90.00  106
  5  ω    -27.00  26.00   0.50    0.20    --   48.87 -19.00  90.00  106
  6  ω    -27.00  26.00   0.50    0.20    --   48.87 -19.00 -60.00  106
  7  ω    -43.00 -13.00   0.50    0.60    --  -88.50  38.00  90.00   60
  8  ω    -43.00 -13.00   0.50    0.60    --  -88.50  38.00   0.00   60
  9  ω    -66.00 -17.00   0.50    0.60    --  -88.50  57.00 -90.00   98
 10  ω    -43.00 -13.00   0.50    0.60    --  -88.50  38.00 120.00   60
 11  ω    -43.00 -13.00   0.50    0.60    --  -88.50  38.00 150.00   60
 12  ω   -164.00 -75.00   0.50    0.60    --  -88.50 -38.00 -30.00  178
 13  ω    -43.00 -13.00   0.50    0.60    --  -88.50  38.00 -30.00   60
 14  ω   -105.00 -22.00   0.50    0.60    --  -88.50  77.00 120.00  166
 15  ω    -43.00 -13.00   0.50    0.60    --  -88.50  38.00 -60.00   60
 16  ω    -43.00 -13.00   0.50    0.60    --  -88.50  38.00  60.00   60
 17  ω     38.00  66.00   0.50    0.60    --  110.00 -57.00 -90.00   56
 18  ω     38.00  66.00   0.50    0.60    --  110.00 -57.00 -60.00   56
 19  ω     38.00  66.00   0.50    0.60    --  110.00 -57.00  90.00   56
 20  ω     38.00  66.00   0.50    0.60    --  110.00 -57.00 -30.00   56
 21  ω     38.00  66.00   0.50    0.60    --  110.00 -57.00-120.00   56
 22  ω     45.00 105.00   0.50    0.60    --  110.00 -77.00-150.00  120
 23  ω     97.00 178.00   0.50    0.60    --  110.00  19.00-120.00  162
 24  ω     41.00 106.00   0.50    0.60    --  110.00 -99.00-150.00  130
 25  ω   -114.00 -25.00   0.50    0.20    --  -48.87 -77.00 150.00  178
 26  ω   -114.00 -25.00   0.50    0.20    --  -48.87 -77.00-120.00  178
 27  ω   -114.00 -25.00   0.50    0.20    --  -48.87 -77.00  30.00  178
 28  ω     62.00  87.00   0.50    0.20    --   48.87 178.00 -90.00   50
 29  ω     25.00 114.00   0.50    0.20    --   48.87  77.00  90.00  178
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0416635000
_diffrn_orient_matrix_UB_12      -0.0568027000
_diffrn_orient_matrix_UB_13      -0.1176969000
_diffrn_orient_matrix_UB_21      -0.0399277000
_diffrn_orient_matrix_UB_22      -0.0847538000
_diffrn_orient_matrix_UB_23      -0.1426883000
_diffrn_orient_matrix_UB_31      -0.0041601000
_diffrn_orient_matrix_UB_32      0.2448912000
_diffrn_orient_matrix_UB_33      -0.0767636000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2211
_reflns_number_total             2425
_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 1.171.42.96a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.198
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     170
_refine_ls_number_reflns         2425
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0478
_refine_ls_restrained_S_all      1.198
_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)+(0.0258P)²+1.8792P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1290
_refine_ls_wR_factor_ref         0.1303
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C3(H3), C6(H6), C4(H4), C14(H14), C7(H7), C11(H11), C13(H13), C12(H12)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_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
O2 O 0.19865(6) -0.1283(3) 0.6295(2) 0.0220(3) Uani 1 1 d . . . . .
H2 H 0.2191(10) -0.006(5) 0.667(4) 0.033 Uiso 1 1 d . U . . .
O1 O 0.44523(5) 0.5420(3) 0.59985(19) 0.0207(3) Uani 1 1 d . . . . .
N2 N 0.22136(6) 0.2848(3) 0.7553(2) 0.0184(4) Uani 1 1 d . . . . .
N1 N 0.25270(7) 0.4591(3) 0.8116(2) 0.0197(4) Uani 1 1 d . . . . .
H1 H 0.2381(9) 0.587(5) 0.846(3) 0.024 Uiso 1 1 d . U . . .
C10 C 0.14977(8) -0.0730(4) 0.6479(3) 0.0190(4) Uani 1 1 d . . . . .
C5 C 0.30085(8) 0.4777(4) 0.7539(3) 0.0178(4) Uani 1 1 d . . . . .
C8 C 0.17435(8) 0.3117(4) 0.7767(3) 0.0185(4) Uani 1 1 d . . . . .
H8 H 0.163900 0.449672 0.828585 0.022 Uiso 1 1 calc R U . . .
C3 C 0.36998(8) 0.3355(4) 0.6069(3) 0.0195(4) Uani 1 1 d . . . . .
H3 H 0.384058 0.220041 0.539240 0.023 Uiso 1 1 calc R U . . .
C9 C 0.13708(8) 0.1372(4) 0.7240(3) 0.0182(4) Uani 1 1 d . . . . .
C6 C 0.32887(8) 0.6725(4) 0.8043(3) 0.0194(4) Uani 1 1 d . . . . .
H6 H 0.314876 0.787758 0.872368 0.023 Uiso 1 1 calc R U . . .
C2 C 0.39795(8) 0.5309(4) 0.6571(3) 0.0180(4) Uani 1 1 d . . . . .
C4 C 0.32164(8) 0.3085(4) 0.6553(3) 0.0189(4) Uani 1 1 d . . . . .
H4 H 0.302774 0.174741 0.621039 0.023 Uiso 1 1 calc R U . . .
C14 C 0.08629(8) 0.1792(4) 0.7431(3) 0.0204(4) Uani 1 1 d . . . . .
H14 H 0.077069 0.318394 0.796387 0.024 Uiso 1 1 calc R U . . .
C7 C 0.37740(8) 0.6995(4) 0.7554(3) 0.0195(4) Uani 1 1 d . . . . .
H7 H 0.396297 0.833309 0.789391 0.023 Uiso 1 1 calc R U . . .
C11 C 0.11254(8) -0.2285(4) 0.5879(3) 0.0218(5) Uani 1 1 d . . . . .
H11 H 0.121346 -0.368012 0.534135 0.026 Uiso 1 1 calc R U . . .
C13 C 0.04932(8) 0.0230(4) 0.6864(3) 0.0231(5) Uani 1 1 d . . . . .
H13 H 0.015154 0.053982 0.701787 0.028 Uiso 1 1 calc R U . . .
C12 C 0.06252(8) -0.1801(4) 0.6064(3) 0.0230(5) Uani 1 1 d . . . . .
H12 H 0.037155 -0.286082 0.564247 0.028 Uiso 1 1 calc R U . . .
C1 C 0.47434(8) 0.7417(4) 0.6482(3) 0.0247(5) Uani 1 1 d . . . . .
H1A H 0.457604 0.878360 0.595635 0.037 Uiso 1 1 calc R U . . .
H1B H 0.507737 0.726478 0.607262 0.037 Uiso 1 1 calc R U . . .
H1C H 0.477684 0.757517 0.775056 0.037 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
O2 H2 0.93(3) . ?
O2 C10 1.367(3) . ?
O1 C2 1.381(2) . ?
O1 C1 1.427(3) . ?
N2 N1 1.359(2) . ?
N2 C8 1.293(3) . ?
N1 H1 0.89(3) . ?
N1 C5 1.407(3) . ?
C10 C9 1.410(3) . ?
C10 C11 1.391(3) . ?
C5 C6 1.392(3) . ?
C5 C4 1.392(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.452(3) . ?
C3 H3 0.9500 . ?
C3 C2 1.394(3) . ?
C3 C4 1.389(3) . ?
C9 C14 1.402(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.395(3) . ?
C2 C7 1.385(3) . ?
C4 H4 0.9500 . ?
C14 H14 0.9500 . ?
C14 C13 1.382(3) . ?
C7 H7 0.9500 . ?
C11 H11 0.9500 . ?
C11 C12 1.388(3) . ?
C13 H13 0.9500 . ?
C13 C12 1.393(3) . ?
C12 H12 0.9500 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 O2 H2 109.2(17) . . ?
C2 O1 C1 116.57(17) . . ?
C8 N2 N1 116.55(18) . . ?
N2 N1 H1 116.1(16) . . ?
N2 N1 C5 120.76(18) . . ?
C5 N1 H1 118.1(17) . . ?
O2 C10 C9 121.16(19) . . ?
O2 C10 C11 118.31(19) . . ?
C11 C10 C9 120.53(19) . . ?
C6 C5 N1 117.31(19) . . ?
C6 C5 C4 119.62(19) . . ?
C4 C5 N1 123.04(19) . . ?
N2 C8 H8 119.0 . . ?
N2 C8 C9 122.0(2) . . ?
C9 C8 H8 119.0 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C4 C3 C2 120.4(2) . . ?
C10 C9 C8 122.31(19) . . ?
C14 C9 C10 117.97(19) . . ?
C14 C9 C8 119.69(19) . . ?
C5 C6 H6 119.8 . . ?
C5 C6 C7 120.4(2) . . ?
C7 C6 H6 119.8 . . ?
O1 C2 C3 115.61(19) . . ?
O1 C2 C7 124.53(19) . . ?
C7 C2 C3 119.85(19) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 C5 119.94(19) . . ?
C3 C4 H4 120.0 . . ?
C9 C14 H14 119.2 . . ?
C13 C14 C9 121.6(2) . . ?
C13 C14 H14 119.2 . . ?
C6 C7 H7 120.1 . . ?
C2 C7 C6 119.8(2) . . ?
C2 C7 H7 120.1 . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 120.0(2) . . ?
C12 C11 H11 120.0 . . ?
C14 C13 H13 120.2 . . ?
C14 C13 C12 119.5(2) . . ?
C12 C13 H13 120.2 . . ?
C11 C12 C13 120.4(2) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 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
O2 C10 C9 C8 3.9(3) . . . . ?
O2 C10 C9 C14 -178.19(18) . . . . ?
O2 C10 C11 C12 179.10(19) . . . . ?
O1 C2 C7 C6 179.05(19) . . . . ?
N2 N1 C5 C6 174.05(18) . . . . ?
N2 N1 C5 C4 -8.1(3) . . . . ?
N2 C8 C9 C10 0.7(3) . . . . ?
N2 C8 C9 C14 -177.17(19) . . . . ?
N1 N2 C8 C9 -179.30(18) . . . . ?
N1 C5 C6 C7 178.42(19) . . . . ?
N1 C5 C4 C3 -178.19(19) . . . . ?
C10 C9 C14 C13 -1.3(3) . . . . ?
C10 C11 C12 C13 -0.6(3) . . . . ?
C5 C6 C7 C2 -0.4(3) . . . . ?
C8 N2 N1 C5 -162.61(19) . . . . ?
C8 C9 C14 C13 176.6(2) . . . . ?
C3 C2 C7 C6 0.3(3) . . . . ?
C9 C10 C11 C12 -1.6(3) . . . . ?
C9 C14 C13 C12 -0.7(3) . . . . ?
C6 C5 C4 C3 -0.4(3) . . . . ?
C2 C3 C4 C5 0.2(3) . . . . ?
C4 C5 C6 C7 0.5(3) . . . . ?
C4 C3 C2 O1 -179.05(18) . . . . ?
C4 C3 C2 C7 -0.2(3) . . . . ?
C14 C13 C12 C11 1.7(3) . . . . ?
C11 C10 C9 C8 -175.38(19) . . . . ?
C11 C10 C9 C14 2.5(3) . . . . ?
C1 O1 C2 C3 179.38(18) . . . . ?
C1 O1 C2 C7 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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.500
_oxdiff_exptl_absorpt_empirical_full_min 0.757
####################################################################### 
# 
# 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_ps_dok63_no3
_database_code_depnum_ccdc_archive 'CCDC 2350545'
loop_
_audit_author_name
_audit_author_address
'Paulina Sobczak'
;Lodz University of Technology
Poland
;
_audit_update_record             
;
2024-04-23 deposited with the CCDC.	2025-01-10 downloaded from the CCDC.
;
_audit_creation_date             2023-12-07
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H13 N3 O3'
_chemical_formula_sum            'C14 H13 N3 O3'
_chemical_formula_weight         271.27
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C14 H13 N3 O3'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   14.3070(3)
_cell_length_b                   7.29090(10)
_cell_length_c                   13.4037(2)
_cell_angle_alpha                90
_cell_angle_beta                 114.076(2)
_cell_angle_gamma                90
_cell_volume                     1276.52(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9894
_cell_measurement_temperature    99.9(5)
_cell_measurement_theta_max      79.3820
_cell_measurement_theta_min      6.5940
_shelx_estimated_absorpt_T_max   0.919
_shelx_estimated_absorpt_T_min   0.793
_exptl_absorpt_coefficient_mu    0.845
_exptl_absorpt_correction_T_max  0.940
_exptl_absorpt_correction_T_min  0.849
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.68a (Rigaku Oxford Diffraction, 2022)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             568
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -3 5 0.0696
-8 1 6 0.0797
3 2 -8 0.0846
7 0 -8 0.1175
7 -3 -2 0.1370
1 -5 -1 0.0423
2 4 2 0.0763
-7 0 -3 0.0963
-3 -4 -3 0.0481
3 -3 -7 0.0652
0 -1 -8 0.0665
-2 2 7 0.0345
3 4 0 0.0727

_exptl_crystal_size_max          0.287
_exptl_crystal_size_mid          0.195
_exptl_crystal_size_min          0.102
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1.1053 -3.2278 5.3081 -0.1331 -0.5501 -0.8244
-8.2316 1.4840 5.8554 -0.1807 -0.7595 0.6249
3.1899 2.1483 -7.7494 0.2115 0.8808 0.4237
6.6156 0.4683 -8.0483 0.2315 0.9681 -0.0961
7.2907 -2.8950 -2.0053 0.0779 0.3324 -0.9399
0.8676 -4.6627 -1.4754 -0.6921 0.1668 -0.7023
2.1733 4.1664 2.4471 0.9172 -0.2200 0.3323
-6.9868 0.4066 -2.5170 -0.6399 0.1518 0.7533
-3.2739 -3.7488 -2.7066 -0.9588 0.2297 -0.1670
2.6029 -2.8276 -6.9646 -0.5392 0.7823 -0.3120
-0.0892 -1.2323 -7.6353 -0.5575 0.8104 0.1802
-1.6267 2.2877 7.4360 0.5625 -0.8167 0.1286
2.8177 4.4780 -0.1866 0.8904 0.0715 0.4496

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_unetI/netI     0.0144
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.913
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12901
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.913
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.438
_diffrn_reflns_theta_min         6.620
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(5)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 300K'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.913
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     38.00  66.00   0.50    0.50    --  110.00 -57.00-180.00   56
  2  ω     38.00  66.00   0.50    0.50    --  110.00 -57.00 -60.00   56
  3  ω     38.00  66.00   0.50    0.50    --  110.00 -57.00   0.00   56
  4  ω     38.00  66.00   0.50    0.50    --  110.00 -57.00 -30.00   56
  5  ω     38.00  66.00   0.50    0.50    --  110.00 -57.00  30.00   56
  6  ω     38.00  66.00   0.50    0.50    --  110.00 -57.00 120.00   56
  7  ω     38.00  66.00   0.50    0.50    --  110.00 -57.00 150.00   56
  8  ω     26.00 114.00   0.50    0.20    --   49.12  77.00 -90.00  176
  9  ω     26.00 114.00   0.50    0.20    --   49.12  77.00-180.00  176
 10  ω     94.00 178.00   0.50    0.50    --  110.00  57.00 -90.00  168
 11  ω     26.00 114.00   0.50    0.20    --   49.12  77.00  90.00  176
 12  ω    -26.00  27.00   0.50    0.20    --  -49.12  19.00 -60.00  106
 13  ω    -43.00  26.00   0.50    0.20    --  -49.12  38.00-150.00  138
 14  ω     60.00 122.00   0.50    0.20    --   49.12-178.00  60.00  124
 15  ω    -43.00  26.00   0.50    0.20    --  -49.12  38.00  90.00  138
 16  ω    -26.00  27.00   0.50    0.20    --  -49.12  19.00   0.00  106
 17  ω    -26.00  27.00   0.50    0.20    --  -49.12  19.00 -30.00  106
 18  ω    -43.00 -13.00   0.50    0.50    --  -88.50  38.00 -90.00   60
 19  ω    -43.00 -13.00   0.50    0.50    --  -88.50  38.00-180.00   60
 20  ω    -43.00 -13.00   0.50    0.50    --  -88.50  38.00-120.00   60
 21  ω    -43.00 -13.00   0.50    0.50    --  -88.50  38.00 -60.00   60
 22  ω    -43.00 -13.00   0.50    0.50    --  -88.50  38.00 120.00   60
 23  ω    -43.00 -13.00   0.50    0.50    --  -88.50  38.00  30.00   60
 24  ω   -164.00 -75.00   0.50    0.50    --  -88.50 -19.00 -30.00  178
 25  ω   -160.00 -73.00   0.50    0.50    --  -88.50 -57.00  30.00  174
 26  ω   -160.00 -73.00   0.50    0.50    --  -88.50 -57.00  60.00  174
 27  ω    -87.00 -19.00   0.50    0.50    --  -88.50 125.00 150.00  136
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0829292000
_diffrn_orient_matrix_UB_12      0.1486489000
_diffrn_orient_matrix_UB_13      0.0480558000
_diffrn_orient_matrix_UB_21      0.0167015000
_diffrn_orient_matrix_UB_22      0.0010267000
_diffrn_orient_matrix_UB_23      -0.1064961000
_diffrn_orient_matrix_UB_31      -0.0821892000
_diffrn_orient_matrix_UB_32      0.1501638000
_diffrn_orient_matrix_UB_33      -0.0468824000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2361
_reflns_number_total             2536
_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 1.171.42.68a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.68a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.68a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2536
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0328
_refine_ls_restrained_S_all      1.076
_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)+(0.0512P)²+0.3545P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0900
_refine_ls_wR_factor_ref         0.0912
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C10(H10), C3(H3), C11(H11), C14(H14), C6(H6), C13(H13), C8(H8), C4(H4)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_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
O1 O 0.92284(5) 0.42324(10) 0.04466(5) 0.01785(18) Uani 1 1 d . . . . .
O2 O 0.40017(6) 0.86730(12) 0.58207(7) 0.0269(2) Uani 1 1 d . . . . .
O3 O 0.45259(6) 0.68863(12) 0.72348(7) 0.0288(2) Uani 1 1 d . . . . .
N1 N 0.87051(7) 0.44465(13) 0.43365(7) 0.0184(2) Uani 1 1 d . . . . .
H1 H 0.9083(10) 0.3692(19) 0.4836(11) 0.022 Uiso 1 1 d . U . . .
N2 N 0.78656(6) 0.51399(12) 0.44295(7) 0.0167(2) Uani 1 1 d . . . . .
N3 N 0.45926(7) 0.75151(12) 0.64157(7) 0.0199(2) Uani 1 1 d . . . . .
C5 C 0.87759(8) 0.44235(13) 0.33259(8) 0.0158(2) Uani 1 1 d . . . . .
C7 C 0.97750(7) 0.35792(14) 0.23136(8) 0.0165(2) Uani 1 1 d . . . . .
H7 H 1.036811 0.303050 0.229042 0.020 Uiso 1 1 calc R U . . .
C9 C 0.69473(7) 0.55112(13) 0.55706(8) 0.0158(2) Uani 1 1 d . . . . .
C10 C 0.62006(8) 0.67020(14) 0.48630(8) 0.0166(2) Uani 1 1 d . . . . .
H10 H 0.622150 0.704572 0.418872 0.020 Uiso 1 1 calc R U . . .
C3 C 0.81566(8) 0.51230(14) 0.14015(8) 0.0176(2) Uani 1 1 d . . . . .
H3 H 0.764433 0.562506 0.075587 0.021 Uiso 1 1 calc R U . . .
C2 C 0.90325(8) 0.43499(13) 0.13716(8) 0.0155(2) Uani 1 1 d . . . . .
C12 C 0.54185(7) 0.68460(14) 0.61276(8) 0.0169(2) Uani 1 1 d . . . . .
C11 C 0.54341(8) 0.73804(14) 0.51386(8) 0.0172(2) Uani 1 1 d . . . . .
H11 H 0.492987 0.819277 0.466297 0.021 Uiso 1 1 calc R U . . .
C14 C 0.68996(8) 0.49963(14) 0.65561(8) 0.0175(2) Uani 1 1 d . . . . .
H14 H 0.739799 0.417730 0.703385 0.021 Uiso 1 1 calc R U . . .
C6 C 0.96467(8) 0.36150(14) 0.32828(8) 0.0169(2) Uani 1 1 d . . . . .
H6 H 1.015299 0.308715 0.392338 0.020 Uiso 1 1 calc R U . . .
C13 C 0.61385(8) 0.56614(14) 0.68446(8) 0.0181(2) Uani 1 1 d . . . . .
H13 H 0.610988 0.531633 0.751504 0.022 Uiso 1 1 calc R U . . .
C8 C 0.77838(8) 0.47859(14) 0.53326(8) 0.0169(2) Uani 1 1 d . . . . .
H8 H 0.828385 0.402914 0.585921 0.020 Uiso 1 1 calc R U . . .
C4 C 0.80289(8) 0.51626(14) 0.23792(8) 0.0175(2) Uani 1 1 d . . . . .
H4 H 0.743057 0.569528 0.239855 0.021 Uiso 1 1 calc R U . . .
C1 C 0.84877(8) 0.50257(15) -0.05358(8) 0.0201(2) Uani 1 1 d . . . . .
H1A H 0.872858 0.491776 -0.112087 0.030 Uiso 1 1 calc R U . . .
H1B H 0.839368 0.632335 -0.040971 0.030 Uiso 1 1 calc R U . . .
H1C H 0.783428 0.437845 -0.074878 0.030 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 C2 1.3808(12) . ?
O1 C1 1.4328(12) . ?
O2 N3 1.2302(12) . ?
O3 N3 1.2289(12) . ?
N1 H1 0.865(14) . ?
N1 N2 1.3549(12) . ?
N1 C5 1.3991(13) . ?
N2 C8 1.2889(13) . ?
N3 C12 1.4683(13) . ?
C5 C6 1.4006(14) . ?
C5 C4 1.3915(14) . ?
C7 H7 0.9500 . ?
C7 C2 1.3944(14) . ?
C7 C6 1.3844(14) . ?
C9 C10 1.4028(14) . ?
C9 C14 1.4015(14) . ?
C9 C8 1.4578(14) . ?
C10 H10 0.9500 . ?
C10 C11 1.3836(14) . ?
C3 H3 0.9500 . ?
C3 C2 1.3895(14) . ?
C3 C4 1.3953(14) . ?
C12 C11 1.3905(14) . ?
C12 C13 1.3867(15) . ?
C11 H11 0.9500 . ?
C14 H14 0.9500 . ?
C14 C13 1.3834(15) . ?
C6 H6 0.9500 . ?
C13 H13 0.9500 . ?
C8 H8 0.9500 . ?
C4 H4 0.9500 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?

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
C2 O1 C1 117.08(8) . . ?
N2 N1 H1 117.7(9) . . ?
N2 N1 C5 120.70(8) . . ?
C5 N1 H1 118.2(9) . . ?
C8 N2 N1 115.80(9) . . ?
O2 N3 C12 118.13(9) . . ?
O3 N3 O2 123.50(9) . . ?
O3 N3 C12 118.37(9) . . ?
N1 C5 C6 117.51(9) . . ?
C4 C5 N1 123.11(9) . . ?
C4 C5 C6 119.37(9) . . ?
C2 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C6 C7 C2 119.90(9) . . ?
C10 C9 C8 122.90(9) . . ?
C14 C9 C10 119.12(9) . . ?
C14 C9 C8 117.98(9) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 C9 120.57(9) . . ?
C11 C10 H10 119.7 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 120.04(9) . . ?
C4 C3 H3 120.0 . . ?
O1 C2 C7 115.43(9) . . ?
O1 C2 C3 124.53(9) . . ?
C3 C2 C7 120.02(9) . . ?
C11 C12 N3 119.03(9) . . ?
C13 C12 N3 118.33(9) . . ?
C13 C12 C11 122.61(9) . . ?
C10 C11 C12 118.50(9) . . ?
C10 C11 H11 120.8 . . ?
C12 C11 H11 120.8 . . ?
C9 C14 H14 119.5 . . ?
C13 C14 C9 121.07(9) . . ?
C13 C14 H14 119.5 . . ?
C5 C6 H6 119.8 . . ?
C7 C6 C5 120.49(9) . . ?
C7 C6 H6 119.8 . . ?
C12 C13 H13 120.9 . . ?
C14 C13 C12 118.13(9) . . ?
C14 C13 H13 120.9 . . ?
N2 C8 C9 122.01(9) . . ?
N2 C8 H8 119.0 . . ?
C9 C8 H8 119.0 . . ?
C5 C4 C3 120.16(9) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 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
O2 N3 C12 C11 -7.19(14) . . . . ?
O2 N3 C12 C13 174.53(9) . . . . ?
O3 N3 C12 C11 172.58(9) . . . . ?
O3 N3 C12 C13 -5.70(14) . . . . ?
N1 N2 C8 C9 177.09(9) . . . . ?
N1 C5 C6 C7 -178.69(9) . . . . ?
N1 C5 C4 C3 178.84(9) . . . . ?
N2 N1 C5 C6 -177.34(9) . . . . ?
N2 N1 C5 C4 2.77(15) . . . . ?
N3 C12 C11 C10 -178.30(9) . . . . ?
N3 C12 C13 C14 178.32(9) . . . . ?
C5 N1 N2 C8 167.20(9) . . . . ?
C9 C10 C11 C12 -0.38(15) . . . . ?
C9 C14 C13 C12 0.37(15) . . . . ?
C10 C9 C14 C13 -0.83(15) . . . . ?
C10 C9 C8 N2 -2.84(16) . . . . ?
C2 C7 C6 C5 -0.11(15) . . . . ?
C2 C3 C4 C5 -0.20(15) . . . . ?
C11 C12 C13 C14 0.10(15) . . . . ?
C14 C9 C10 C11 0.83(15) . . . . ?
C14 C9 C8 N2 177.63(9) . . . . ?
C6 C5 C4 C3 -1.05(15) . . . . ?
C6 C7 C2 O1 -179.55(9) . . . . ?
C6 C7 C2 C3 -1.15(15) . . . . ?
C13 C12 C11 C10 -0.10(15) . . . . ?
C8 C9 C10 C11 -178.69(9) . . . . ?
C8 C9 C14 C13 178.71(9) . . . . ?
C4 C5 C6 C7 1.21(15) . . . . ?
C4 C3 C2 O1 179.56(9) . . . . ?
C4 C3 C2 C7 1.31(15) . . . . ?
C1 O1 C2 C7 -179.38(9) . . . . ?
C1 O1 C2 C3 2.30(14) . . . . ?

_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 1.985
_oxdiff_exptl_absorpt_empirical_full_min 0.651
####################################################################### 
# 
# 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_ps_dok64
_database_code_depnum_ccdc_archive 'CCDC 2350548'
loop_
_audit_author_name
_audit_author_address
'Paulina Sobczak'
;Lodz University of Technology
Poland
;
_audit_update_record             
;
2024-04-23 deposited with the CCDC.	2025-01-10 downloaded from the CCDC.
;
_audit_creation_date             2023-12-07
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H21 N3 O2'
_chemical_formula_sum            'C18 H21 N3 O2'
_chemical_formula_weight         311.38
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C18 H21 N3 O2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.97860(10)
_cell_length_b                   7.24420(10)
_cell_length_c                   36.2940(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1571.90(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    18920
_cell_measurement_temperature    99.9(6)
_cell_measurement_theta_max      79.5090
_cell_measurement_theta_min      4.8510
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.851
_exptl_absorpt_coefficient_mu    0.702
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.913
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.96a (Rigaku Oxford Diffraction, 2023)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             664
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -5 4 0.0375
0 5 -4 0.0481
-1 4 -5 0.0493
2 -4 6 0.0222
-4 1 -6 0.0927
0 1 23 0.0097
4 1 1 0.1173
0 -1 -23 0.0116

_exptl_crystal_size_max          0.238
_exptl_crystal_size_mid          0.074
_exptl_crystal_size_min          0.025
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.1651 -4.6418 3.6097 -0.2301 -0.9626 0.1431
0.1879 4.6414 -3.5802 0.2299 0.9617 -0.1490
-1.4172 4.2466 -5.3084 0.2240 0.9340 0.2784
1.6800 -4.0925 5.5178 -0.2185 -0.9108 -0.3503
-3.6151 1.2814 -5.6790 0.0950 0.3903 0.9158
-0.0751 0.8496 23.1680 0.9554 -0.2283 -0.1872
3.8545 0.5131 1.0152 -0.1405 0.0354 -0.9894
0.1996 -0.8337 -23.1552 -0.9608 0.2296 0.1554

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0644
_diffrn_reflns_av_unetI/netI     0.0847
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_number            29983
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.557
_diffrn_reflns_theta_min         4.874
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(6)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 300K'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -114.00 -25.00   0.50    4.00    --  -48.87 -77.00-150.00  178
  2  ω    -26.00  27.00   0.50    4.00    --  -48.87  19.00 -60.00  106
  3  ω   -124.00 -35.00   0.50    4.00    --  -48.87 -38.00 120.00  178
  4  ω    -27.00  26.00   0.50    4.00    --   48.87 -19.00  30.00  106
  5  ω    -23.00 121.00   0.50    4.00    --   48.87   0.00  60.00  288
  6  ω     60.00 122.00   0.50    4.00    --   48.87-178.00   0.00  124
  7  ω     60.00 122.00   0.50    4.00    --   48.87-178.00  60.00  124
  8  ω    -43.00 -13.00   0.50   16.00    --  -88.50  38.00   0.00   60
  9  ω    -43.00 -13.00   0.50   16.00    --  -88.50  38.00 -30.00   60
 10  ω    -66.00 -17.00   0.50   16.00    --  -88.50  57.00 -60.00   98
 11  ω   -164.00 -75.00   0.50   16.00    --  -88.50 -19.00 150.00  178
 12  ω    -43.00 -13.00   0.50   16.00    --  -88.50  38.00-180.00   60
 13  ω    -66.00 -17.00   0.50   16.00    --  -88.50  57.00-120.00   98
 14  ω   -105.00 -22.00   0.50   16.00    --  -88.50  77.00 120.00  166
 15  ω   -164.00 -75.00   0.50   16.00    --  -88.50 -19.00  60.00  178
 16  ω    -43.00 -13.00   0.50   16.00    --  -88.50  38.00 -60.00   60
 17  ω    -43.00 -13.00   0.50   16.00    --  -88.50  38.00  30.00   60
 18  ω    -43.00 -13.00   0.50   16.00    --  -88.50  38.00 -90.00   60
 19  ω     38.00  66.00   0.50   16.00    --  110.00 -57.00 120.00   56
 20  ω     41.00 113.00   0.50   16.00    --  110.00-125.00  90.00  144
 21  ω     41.00 113.00   0.50   16.00    --  110.00-125.00 -60.00  144
 22  ω     45.00 105.00   0.50   16.00    --  110.00 -77.00-150.00  120
 23  ω     38.00  66.00   0.50   16.00    --  110.00 -57.00 -90.00   56
 24  ω     38.00  66.00   0.50   16.00    --  110.00 -57.00 -30.00   56
 25  ω     41.00 106.00   0.50   16.00    --  110.00 -99.00 120.00  130
 26  ω     94.00 178.00   0.50   16.00    --  110.00  57.00-180.00  168
 27  ω     41.00 113.00   0.50   16.00    --  110.00-125.00-150.00  144
 28  ω     41.00 113.00   0.50   16.00    --  110.00-125.00  30.00  144
 29  ω     38.00  66.00   0.50   16.00    --  110.00 -57.00   0.00   56
 30  ω     97.00 178.00   0.50   16.00    --  110.00  19.00 150.00  162
 31  ω     41.00 106.00   0.50   16.00    --  110.00 -99.00 -30.00  130
 32  ω     97.00 178.00   0.50   16.00    --  110.00  19.00  90.00  162
 33  ω     38.00  66.00   0.50   16.00    --  110.00 -57.00 -60.00   56
 34  ω     38.00  66.00   0.50   16.00    --  110.00 -57.00  30.00   56
 35  ω   -114.00 -25.00   0.50    4.00    --  -48.87 -77.00  90.00  178
 36  ω   -114.00 -25.00   0.50    4.00    --  -48.87 -77.00 150.00  178
 37  ω   -114.00 -25.00   0.50    4.00    --  -48.87 -77.00  60.00  178
 38  ω   -114.00 -25.00   0.50    4.00    --  -48.87 -77.00 -30.00  178
 39  ω   -120.00 -33.00   0.50    4.00    --  -48.87 -57.00 -90.00  174
 40  ω   -114.00 -25.00   0.50    4.00    --  -48.87 -77.00-120.00  178
 41  ω     33.00 121.00   0.50    4.00    --   48.87  57.00  60.00  176
 42  ω     33.00 121.00   0.50    4.00    --   48.87  57.00 -30.00  176
 43  ω     97.00 166.00   0.50   16.00    --  110.00  19.00 -90.00  138
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0572934000
_diffrn_orient_matrix_UB_12      0.0812140000
_diffrn_orient_matrix_UB_13      0.0380756000
_diffrn_orient_matrix_UB_21      -0.0122393000
_diffrn_orient_matrix_UB_22      0.1945718000
_diffrn_orient_matrix_UB_23      -0.0170276000
_diffrn_orient_matrix_UB_31      -0.2508998000
_diffrn_orient_matrix_UB_32      -0.0280171000
_diffrn_orient_matrix_UB_33      -0.0078655000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.647
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.937
_reflns_number_gt                3120
_reflns_number_total             3310
_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 1.171.42.96a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 
;
 Flack x determined using 1179 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.11(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.194
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3310
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0598
_refine_ls_restrained_S_all      1.194
_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)+(0.0310P)²+0.8071P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0936
_refine_ls_wR_factor_ref         0.0953
_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.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C17(H17A,H17B), C16(H16A,H16B), C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C13(H13), C11(H11), C10(H10), C4(H4), C6(H6), C8(H8), C7(H7), C3(H3)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_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
C14 C 0.4810(4) 0.5922(3) 0.50757(6) 0.0169(5) Uani 1 1 d . . . . .
H14 H 0.344361 0.651698 0.513677 0.020 Uiso 1 1 calc R U . . .
N2 N 0.7340(4) 0.6007(3) 0.59882(5) 0.0172(4) Uani 1 1 d . . . . .
C12 C 0.7197(4) 0.4537(3) 0.46103(6) 0.0152(5) Uani 1 1 d . . . . .
C13 C 0.5233(4) 0.5455(3) 0.47116(6) 0.0172(5) Uani 1 1 d . . . . .
H13 H 0.416797 0.576571 0.452753 0.021 Uiso 1 1 calc R U . . .
C11 C 0.8732(4) 0.4106(3) 0.48937(6) 0.0170(5) Uani 1 1 d . . . . .
H11 H 1.007053 0.346229 0.483527 0.020 Uiso 1 1 calc R U . . .
N1 N 0.6751(4) 0.6640(3) 0.63295(5) 0.0196(4) Uani 1 1 d . . . . .
H1 H 0.563(5) 0.737(4) 0.6343(8) 0.023 Uiso 1 1 d . U . . .
N3 N 0.7627(3) 0.4042(3) 0.42397(5) 0.0173(4) Uani 1 1 d . . . . .
O1 O 1.3149(3) 0.6514(2) 0.74439(4) 0.0232(4) Uani 1 1 d . . . . .
C9 C 0.6349(4) 0.5536(3) 0.53540(6) 0.0160(5) Uani 1 1 d . . . . .
C10 C 0.8315(4) 0.4607(3) 0.52549(6) 0.0166(5) Uani 1 1 d . . . . .
H10 H 0.938393 0.431644 0.543974 0.020 Uiso 1 1 calc R U . . .
C4 C 1.0409(4) 0.5725(3) 0.65668(6) 0.0179(5) Uani 1 1 d . . . . .
H4 H 1.073876 0.510229 0.634296 0.022 Uiso 1 1 calc R U . . .
C5 C 0.8364(4) 0.6643(3) 0.66089(6) 0.0169(5) Uani 1 1 d . . . . .
C6 C 0.7916(4) 0.7559(3) 0.69394(6) 0.0186(5) Uani 1 1 d . . . . .
H6 H 0.653351 0.818779 0.697009 0.022 Uiso 1 1 calc R U . . .
C8 C 0.5875(4) 0.6152(3) 0.57300(6) 0.0163(5) Uani 1 1 d . . . . .
H8 H 0.445361 0.667042 0.578468 0.020 Uiso 1 1 calc R U . . .
C7 C 0.9479(4) 0.7560(3) 0.72246(6) 0.0193(5) Uani 1 1 d . . . . .
H7 H 0.916071 0.818939 0.744825 0.023 Uiso 1 1 calc R U . . .
C2 C 1.1501(4) 0.6641(3) 0.71816(6) 0.0187(5) Uani 1 1 d . . . . .
C15 C 0.9970(4) 0.3802(3) 0.41424(6) 0.0185(5) Uani 1 1 d . . . . .
H15A H 1.064491 0.285999 0.430592 0.022 Uiso 1 1 calc R U . . .
H15B H 1.077537 0.497883 0.418229 0.022 Uiso 1 1 calc R U . . .
C1 C 1.2822(5) 0.7525(4) 0.77771(7) 0.0288(6) Uani 1 1 d . . . . .
H1A H 1.270130 0.884384 0.772074 0.043 Uiso 1 1 calc R U . . .
H1B H 1.409474 0.731830 0.794215 0.043 Uiso 1 1 calc R U . . .
H1C H 1.144437 0.710552 0.789729 0.043 Uiso 1 1 calc R U . . .
C3 C 1.1948(5) 0.5724(3) 0.68514(6) 0.0200(5) Uani 1 1 d . . . . .
H3 H 1.332796 0.509021 0.682176 0.024 Uiso 1 1 calc R U . . .
O2 O 0.9178(3) 0.4479(3) 0.35007(4) 0.0232(4) Uani 1 1 d . . . . .
C17 C 0.6851(4) 0.4434(3) 0.35731(6) 0.0194(5) Uani 1 1 d . . . . .
H17A H 0.628800 0.316318 0.353530 0.023 Uiso 1 1 calc R U . . .
H17B H 0.607008 0.525352 0.339662 0.023 Uiso 1 1 calc R U . . .
C16 C 1.0253(4) 0.3207(3) 0.37445(6) 0.0198(5) Uani 1 1 d . . . . .
H16A H 1.186575 0.313826 0.368426 0.024 Uiso 1 1 calc R U . . .
H16B H 0.960151 0.196205 0.371059 0.024 Uiso 1 1 calc R U . . .
C18 C 0.6317(4) 0.5047(3) 0.39637(6) 0.0184(5) Uani 1 1 d . . . . .
H18A H 0.662529 0.638456 0.398729 0.022 Uiso 1 1 calc R U . . .
H18B H 0.470518 0.485024 0.401199 0.022 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
C14 H14 0.9500 . ?
C14 C13 1.387(3) . ?
C14 C9 1.395(3) . ?
N2 N1 1.367(3) . ?
N2 C8 1.287(3) . ?
C12 C13 1.399(3) . ?
C12 C11 1.413(3) . ?
C12 N3 1.415(3) . ?
C13 H13 0.9500 . ?
C11 H11 0.9500 . ?
C11 C10 1.383(3) . ?
N1 H1 0.86(3) . ?
N1 C5 1.399(3) . ?
N3 C15 1.455(3) . ?
N3 C18 1.465(3) . ?
O1 C2 1.373(3) . ?
O1 C1 1.427(3) . ?
C9 C10 1.401(3) . ?
C9 C8 1.463(3) . ?
C10 H10 0.9500 . ?
C4 H4 0.9500 . ?
C4 C5 1.400(3) . ?
C4 C3 1.383(3) . ?
C5 C6 1.397(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.395(3) . ?
C8 H8 0.9500 . ?
C7 H7 0.9500 . ?
C7 C2 1.389(3) . ?
C2 C3 1.396(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.517(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C3 H3 0.9500 . ?
O2 C17 1.416(3) . ?
O2 C16 1.430(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.519(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?

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
C13 C14 H14 119.3 . . ?
C13 C14 C9 121.4(2) . . ?
C9 C14 H14 119.3 . . ?
C8 N2 N1 117.2(2) . . ?
C13 C12 C11 117.3(2) . . ?
C13 C12 N3 121.5(2) . . ?
C11 C12 N3 121.2(2) . . ?
C14 C13 C12 121.3(2) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C12 C11 H11 119.5 . . ?
C10 C11 C12 121.0(2) . . ?
C10 C11 H11 119.5 . . ?
N2 N1 H1 117.3(19) . . ?
N2 N1 C5 118.7(2) . . ?
C5 N1 H1 120.0(19) . . ?
C12 N3 C15 115.82(19) . . ?
C12 N3 C18 115.29(19) . . ?
C15 N3 C18 114.08(19) . . ?
C2 O1 C1 117.1(2) . . ?
C14 C9 C10 117.6(2) . . ?
C14 C9 C8 119.1(2) . . ?
C10 C9 C8 123.2(2) . . ?
C11 C10 C9 121.4(2) . . ?
C11 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 120.0(2) . . ?
N1 C5 C4 121.5(2) . . ?
C6 C5 N1 119.4(2) . . ?
C6 C5 C4 119.1(2) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 C5 120.6(2) . . ?
C7 C6 H6 119.7 . . ?
N2 C8 C9 121.5(2) . . ?
N2 C8 H8 119.3 . . ?
C9 C8 H8 119.3 . . ?
C6 C7 H7 120.0 . . ?
C2 C7 C6 120.0(2) . . ?
C2 C7 H7 120.0 . . ?
O1 C2 C7 125.3(2) . . ?
O1 C2 C3 115.2(2) . . ?
C7 C2 C3 119.4(2) . . ?
N3 C15 H15A 109.2 . . ?
N3 C15 H15B 109.2 . . ?
N3 C15 C16 111.87(19) . . ?
H15A C15 H15B 107.9 . . ?
C16 C15 H15A 109.2 . . ?
C16 C15 H15B 109.2 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C4 C3 C2 120.9(2) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C17 O2 C16 108.17(18) . . ?
O2 C17 H17A 109.2 . . ?
O2 C17 H17B 109.2 . . ?
O2 C17 C18 111.9(2) . . ?
H17A C17 H17B 107.9 . . ?
C18 C17 H17A 109.2 . . ?
C18 C17 H17B 109.2 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
O2 C16 C15 110.86(19) . . ?
O2 C16 H16A 109.5 . . ?
O2 C16 H16B 109.5 . . ?
H16A C16 H16B 108.1 . . ?
N3 C18 C17 112.4(2) . . ?
N3 C18 H18A 109.1 . . ?
N3 C18 H18B 109.1 . . ?
C17 C18 H18A 109.1 . . ?
C17 C18 H18B 109.1 . . ?
H18A C18 H18B 107.9 . . ?

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
C14 C9 C10 C11 0.6(3) . . . . ?
C14 C9 C8 N2 -172.4(2) . . . . ?
N2 N1 C5 C4 -11.5(3) . . . . ?
N2 N1 C5 C6 169.4(2) . . . . ?
C12 C11 C10 C9 0.9(3) . . . . ?
C12 N3 C15 C16 177.93(19) . . . . ?
C12 N3 C18 C17 -179.5(2) . . . . ?
C13 C14 C9 C10 -1.9(3) . . . . ?
C13 C14 C9 C8 176.5(2) . . . . ?
C13 C12 C11 C10 -1.2(3) . . . . ?
C13 C12 N3 C15 156.0(2) . . . . ?
C13 C12 N3 C18 19.1(3) . . . . ?
C11 C12 C13 C14 -0.1(3) . . . . ?
C11 C12 N3 C15 -24.5(3) . . . . ?
C11 C12 N3 C18 -161.4(2) . . . . ?
N1 N2 C8 C9 179.3(2) . . . . ?
N1 C5 C6 C7 179.0(2) . . . . ?
N3 C12 C13 C14 179.4(2) . . . . ?
N3 C12 C11 C10 179.4(2) . . . . ?
N3 C15 C16 O2 55.4(3) . . . . ?
O1 C2 C3 C4 179.1(2) . . . . ?
C9 C14 C13 C12 1.6(4) . . . . ?
C10 C9 C8 N2 5.9(3) . . . . ?
C4 C5 C6 C7 -0.1(3) . . . . ?
C5 C4 C3 C2 -0.5(3) . . . . ?
C5 C6 C7 C2 -0.1(4) . . . . ?
C6 C7 C2 O1 -178.7(2) . . . . ?
C6 C7 C2 C3 0.1(3) . . . . ?
C8 N2 N1 C5 -174.8(2) . . . . ?
C8 C9 C10 C11 -177.7(2) . . . . ?
C7 C2 C3 C4 0.2(3) . . . . ?
C15 N3 C18 C17 42.9(3) . . . . ?
C1 O1 C2 C7 -4.9(3) . . . . ?
C1 O1 C2 C3 176.3(2) . . . . ?
C3 C4 C5 N1 -178.7(2) . . . . ?
C3 C4 C5 C6 0.4(3) . . . . ?
O2 C17 C18 N3 -52.0(3) . . . . ?
C17 O2 C16 C15 -63.9(3) . . . . ?
C16 O2 C17 C18 62.2(2) . . . . ?
C18 N3 C15 C16 -44.7(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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.005
_oxdiff_exptl_absorpt_empirical_full_min 0.614
####################################################################### 
# 
# 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_ps_dok66
_database_code_depnum_ccdc_archive 'CCDC 2350547'
loop_
_audit_author_name
_audit_author_address
'Paulina Sobczak'
;Lodz University of Technology
Poland
;
_audit_update_record             
;
2024-04-23 deposited with the CCDC.	2025-01-10 downloaded from the CCDC.
;
_audit_creation_date             2023-12-07
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H15 N3 O3'
_chemical_formula_sum            'C16 H15 N3 O3'
_chemical_formula_weight         297.31
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C16 H15 N3 O3'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   16.2030(2)
_cell_length_b                   13.03460(10)
_cell_length_c                   6.76630(10)
_cell_angle_alpha                90
_cell_angle_beta                 94.0550(10)
_cell_angle_gamma                90
_cell_volume                     1425.46(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    16395
_cell_measurement_temperature    99.9(6)
_cell_measurement_theta_max      79.3270
_cell_measurement_theta_min      4.3160
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.875
_exptl_absorpt_coefficient_mu    0.808
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_correction_T_min  0.911
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.68a (Rigaku Oxford Diffraction, 2022)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             624
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 7 2 0.0616
0 -6 3 0.0662
1 -1 -4 0.0588
10 1 0 0.0171
-10 -1 0 0.0031
9 -2 -2 0.0443
9 3 1 0.0429
-1 8 -1 0.0710
1 -8 0 0.0668
1 -8 2 0.0599

_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.136
_exptl_crystal_size_min          0.02
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.9563 7.2837 2.2225 0.3215 0.2770 -0.9055
0.1997 -5.6920 3.2350 -0.7408 -0.6332 -0.2243
0.5401 -0.5883 -4.3815 0.3878 0.3298 0.8607
10.4610 0.7207 -0.0666 -0.6500 0.7599 -0.0091
-10.4610 -0.7207 0.0666 0.6500 -0.7599 0.0091
9.0000 -2.0000 -2.0000 -0.5306 0.6183 0.5310
9.0000 3.0000 1.0000 -0.5103 0.7400 -0.3649
-1.0000 8.0000 -1.0000 0.7141 0.5705 -0.3504
1.0000 -8.0000 -0.0000 -0.6082 -0.4941 0.5375
1.0000 -8.0000 2.0000 -0.8200 -0.6469 0.1632

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_unetI/netI     0.0140
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            27673
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.579
_diffrn_reflns_theta_min         4.358
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(6)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 300K'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -43.00  27.00   0.50    2.00    --  -48.87  38.00  30.00  140
  2  ω    -72.00  17.00   0.50    2.00    --  -48.87  77.00 120.00  178
  3  ω    -26.00  27.00   0.50    2.00    --  -48.87  19.00 -30.00  106
  4  ω    -26.00  27.00   0.50    2.00    --  -48.87  19.00 120.00  106
  5  ω   -120.00 -33.00   0.50    2.00    --  -48.87 -57.00-150.00  174
  6  ω     36.00 125.00   0.50    2.00    --   48.87  19.00  90.00  178
  7  ω    -27.00  26.00   0.50    2.00    --   48.87 -19.00-180.00  106
  8  ω    -27.00  26.00   0.50    2.00    --   48.87 -19.00 -90.00  106
  9  ω    -43.00 -13.00   0.50    8.00    --  -88.50  38.00-180.00   60
 10  ω    -43.00 -13.00   0.50    8.00    --  -88.50  38.00  90.00   60
 11  ω    -43.00 -13.00   0.50    8.00    --  -88.50  38.00  60.00   60
 12  ω   -160.00 -73.00   0.50    8.00    --  -88.50 -57.00-150.00  174
 13  ω    -43.00 -13.00   0.50    8.00    --  -88.50  38.00  30.00   60
 14  ω    -43.00 -13.00   0.50    8.00    --  -88.50  38.00 -60.00   60
 15  ω   -164.00 -75.00   0.50    8.00    --  -88.50 -19.00-150.00  178
 16  ω    -43.00 -13.00   0.50    8.00    --  -88.50  38.00 150.00   60
 17  ω   -164.00 -75.00   0.50    8.00    --  -88.50 -19.00   0.00  178
 18  ω    -43.00 -13.00   0.50    8.00    --  -88.50  38.00 120.00   60
 19  ω    -87.00 -19.00   0.50    8.00    --  -88.50 125.00  90.00  136
 20  ω    -43.00 -13.00   0.50    8.00    --  -88.50  38.00-120.00   60
 21  ω   -160.00 -73.00   0.50    8.00    --  -88.50 -57.00-180.00  174
 22  ω    -43.00 -13.00   0.50    8.00    --  -88.50  38.00   0.00   60
 23  ω     38.00  66.00   0.50    8.00    --  110.00 -57.00   0.00   56
 24  ω     45.00 105.00   0.50    8.00    --  110.00 -77.00 150.00  120
 25  ω     38.00  66.00   0.50    8.00    --  110.00 -57.00-120.00   56
 26  ω     41.00 106.00   0.50    8.00    --  110.00 -99.00  90.00  130
 27  ω     38.00  66.00   0.50    8.00    --  110.00 -57.00-180.00   56
 28  ω     97.00 178.00   0.50    8.00    --  110.00  19.00 -90.00  162
 29  ω     45.00 105.00   0.50    8.00    --  110.00 -77.00-180.00  120
 30  ω     97.00 178.00   0.50    8.00    --  110.00  19.00 -30.00  162
 31  ω     38.00  66.00   0.50    8.00    --  110.00 -57.00  30.00   56
 32  ω     44.00  98.00   0.50    8.00    --  110.00 -75.00 -17.00  108
 33  ω     41.00 106.00   0.50    8.00    --  110.00 -99.00 -30.00  130
 34  ω     41.00 113.00   0.50    8.00    --  110.00-125.00-180.00  144
 35  ω     38.00  66.00   0.50    8.00    --  110.00 -57.00 -60.00   56
 36  ω     98.00 178.00   0.50    8.00    --  110.00  38.00-150.00  160
 37  ω     38.00  66.00   0.50    8.00    --  110.00 -57.00  60.00   56
 38  ω   -114.00 -25.00   0.50    2.00    --  -48.87 -77.00 -30.00  178
 39  ω   -114.00 -25.00   0.50    2.00    --  -48.87 -77.00   0.00  178
 40  ω   -114.00 -25.00   0.50    2.00    --  -48.87 -77.00  90.00  178
 41  ω   -120.00 -33.00   0.50    2.00    --  -48.87 -57.00  30.00  174
 42  ω   -114.00 -25.00   0.50    2.00    --  -48.87 -77.00-180.00  178
 43  ω     37.00 124.00   0.50    2.00    --   48.87  38.00 150.00  174
 44  ω     33.00 121.00   0.50    2.00    --   48.87  57.00 -60.00  176
 45  ω     37.00 124.00   0.50    2.00    --   48.87  38.00-120.00  174
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0674657000
_diffrn_orient_matrix_UB_12      0.0675940000
_diffrn_orient_matrix_UB_13      -0.1058973000
_diffrn_orient_matrix_UB_21      0.0673183000
_diffrn_orient_matrix_UB_22      0.0701831000
_diffrn_orient_matrix_UB_23      -0.0763975000
_diffrn_orient_matrix_UB_31      0.0025471000
_diffrn_orient_matrix_UB_32      -0.0668752000
_diffrn_orient_matrix_UB_33      -0.1871523000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2757
_reflns_number_total             3013
_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 1.171.42.68a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.68a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.68a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.442
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.275
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         3013
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0612
_refine_ls_restrained_S_all      1.275
_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)+(0.0273P)²+2.9471P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1734
_refine_ls_wR_factor_ref         0.1747
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(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), C9(H9), C16(H16), C4(H4), C3(H3), C6(H6), C10(H10), C12(H12),
 C15(H15), C13(H13)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_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
O1 O 0.75646(12) 0.57315(17) 1.3796(3) 0.0288(5) Uani 1 1 d . . . . .
N1 N 0.58954(14) 0.65269(19) 0.6495(3) 0.0242(5) Uani 1 1 d . . . . .
H1 H 0.619(2) 0.674(3) 0.562(5) 0.029 Uiso 1 1 d . U . . .
N2 N 0.50841(14) 0.63000(18) 0.6144(3) 0.0236(5) Uani 1 1 d . . . . .
O2 O -0.03222(14) 0.6126(2) 0.0175(5) 0.0553(8) Uani 1 1 d . . . . .
C5 C 0.63120(16) 0.6316(2) 0.8338(4) 0.0209(5) Uani 1 1 d . . . . .
C7 C 0.75988(16) 0.6321(2) 1.0375(4) 0.0221(5) Uani 1 1 d . . . . .
H7 H 0.817566 0.645778 1.052778 0.027 Uiso 1 1 calc R U . . .
C8 C 0.47615(17) 0.6503(2) 0.4388(4) 0.0235(6) Uani 1 1 d . . . . .
H8 H 0.509445 0.680143 0.344075 0.028 Uiso 1 1 calc R U . . .
C9 C 0.39072(17) 0.6283(2) 0.3846(4) 0.0234(6) Uani 1 1 d . . . . .
H9 H 0.356617 0.603192 0.482402 0.028 Uiso 1 1 calc R U . . .
C11 C 0.27124(16) 0.6298(2) 0.1247(4) 0.0230(6) Uani 1 1 d . . . . .
C16 C 0.24951(18) 0.6508(2) -0.0739(4) 0.0261(6) Uani 1 1 d . . . . .
H16 H 0.291621 0.667951 -0.158958 0.031 Uiso 1 1 calc R U . . .
C2 C 0.71932(16) 0.5929(2) 1.1945(4) 0.0223(5) Uani 1 1 d . . . . .
C4 C 0.59105(16) 0.5907(2) 0.9898(4) 0.0223(5) Uani 1 1 d . . . . .
H4 H 0.533481 0.576365 0.973866 0.027 Uiso 1 1 calc R U . . .
O3 O 0.00628(17) 0.6328(3) -0.2817(5) 0.0723(10) Uani 1 1 d . . . . .
C3 C 0.63510(16) 0.5707(2) 1.1702(4) 0.0234(6) Uani 1 1 d . . . . .
H3 H 0.607671 0.541832 1.276591 0.028 Uiso 1 1 calc R U . . .
C6 C 0.71584(16) 0.6512(2) 0.8574(4) 0.0225(6) Uani 1 1 d . . . . .
H6 H 0.743676 0.677847 0.749579 0.027 Uiso 1 1 calc R U . . .
C10 C 0.35781(17) 0.6426(2) 0.1982(4) 0.0230(6) Uani 1 1 d . . . . .
H10 H 0.395055 0.663332 0.103498 0.028 Uiso 1 1 calc R U . . .
N3 N 0.02125(17) 0.6229(2) -0.1008(5) 0.0464(8) Uani 1 1 d . . . . .
C12 C 0.20883(17) 0.6018(2) 0.2483(4) 0.0269(6) Uani 1 1 d . . . . .
H12 H 0.222843 0.584923 0.383042 0.032 Uiso 1 1 calc R U . . .
C15 C 0.16809(19) 0.6474(2) -0.1503(5) 0.0316(7) Uani 1 1 d . . . . .
H15 H 0.153866 0.661790 -0.286125 0.038 Uiso 1 1 calc R U . . .
C13 C 0.12671(18) 0.5988(2) 0.1741(5) 0.0312(7) Uani 1 1 d . . . . .
H13 H 0.084144 0.580899 0.257304 0.037 Uiso 1 1 calc R U . . .
C14 C 0.10812(17) 0.6224(2) -0.0234(5) 0.0319(7) Uani 1 1 d . . . . .
C1 C 0.84180(18) 0.6000(3) 1.4122(4) 0.0318(7) Uani 1 1 d . . . . .
H1A H 0.874943 0.556297 1.330518 0.048 Uiso 1 1 calc R U . . .
H1B H 0.859645 0.590199 1.552291 0.048 Uiso 1 1 calc R U . . .
H1C H 0.849374 0.672057 1.375992 0.048 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 C2 1.375(3) . ?
O1 C1 1.429(3) . ?
N1 H1 0.83(3) . ?
N1 N2 1.352(3) . ?
N1 C5 1.403(3) . ?
N2 C8 1.291(3) . ?
O2 N3 1.228(4) . ?
C5 C4 1.385(4) . ?
C5 C6 1.393(4) . ?
C7 H7 0.9500 . ?
C7 C2 1.386(4) . ?
C7 C6 1.391(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.435(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.347(4) . ?
C11 C16 1.392(4) . ?
C11 C10 1.464(4) . ?
C11 C12 1.405(4) . ?
C16 H16 0.9500 . ?
C16 C15 1.383(4) . ?
C2 C3 1.393(4) . ?
C4 H4 0.9500 . ?
C4 C3 1.395(4) . ?
O3 N3 1.238(4) . ?
C3 H3 0.9500 . ?
C6 H6 0.9500 . ?
C10 H10 0.9500 . ?
N3 C14 1.467(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.389(4) . ?
C15 H15 0.9500 . ?
C15 C14 1.381(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.383(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?

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
C2 O1 C1 116.8(2) . . ?
N2 N1 H1 123(2) . . ?
N2 N1 C5 120.9(2) . . ?
C5 N1 H1 116(2) . . ?
C8 N2 N1 116.3(2) . . ?
C4 C5 N1 122.0(2) . . ?
C4 C5 C6 119.7(2) . . ?
C6 C5 N1 118.3(2) . . ?
C2 C7 H7 120.1 . . ?
C2 C7 C6 119.8(2) . . ?
C6 C7 H7 120.1 . . ?
N2 C8 H8 119.5 . . ?
N2 C8 C9 121.0(3) . . ?
C9 C8 H8 119.5 . . ?
C8 C9 H9 119.2 . . ?
C10 C9 C8 121.5(3) . . ?
C10 C9 H9 119.2 . . ?
C16 C11 C10 118.4(3) . . ?
C16 C11 C12 118.8(3) . . ?
C12 C11 C10 122.7(3) . . ?
C11 C16 H16 119.2 . . ?
C15 C16 C11 121.6(3) . . ?
C15 C16 H16 119.2 . . ?
O1 C2 C7 124.5(2) . . ?
O1 C2 C3 115.5(2) . . ?
C7 C2 C3 120.0(2) . . ?
C5 C4 H4 120.0 . . ?
C5 C4 C3 120.0(2) . . ?
C3 C4 H4 120.0 . . ?
C2 C3 C4 120.1(2) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C6 H6 119.8 . . ?
C7 C6 C5 120.5(2) . . ?
C7 C6 H6 119.8 . . ?
C9 C10 C11 127.5(3) . . ?
C9 C10 H10 116.3 . . ?
C11 C10 H10 116.3 . . ?
O2 N3 O3 123.9(3) . . ?
O2 N3 C14 118.1(3) . . ?
O3 N3 C14 118.0(3) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.2(3) . . ?
C13 C12 H12 119.9 . . ?
C16 C15 H15 121.0 . . ?
C14 C15 C16 118.0(3) . . ?
C14 C15 H15 121.0 . . ?
C12 C13 H13 120.6 . . ?
C14 C13 C12 118.7(3) . . ?
C14 C13 H13 120.6 . . ?
C15 C14 N3 118.5(3) . . ?
C15 C14 C13 122.6(3) . . ?
C13 C14 N3 118.9(3) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 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
O1 C2 C3 C4 178.1(2) . . . . ?
N1 N2 C8 C9 179.4(2) . . . . ?
N1 C5 C4 C3 179.7(2) . . . . ?
N1 C5 C6 C7 179.7(2) . . . . ?
N2 N1 C5 C4 -2.6(4) . . . . ?
N2 N1 C5 C6 176.3(2) . . . . ?
N2 C8 C9 C10 -175.4(3) . . . . ?
O2 N3 C14 C15 -171.6(3) . . . . ?
O2 N3 C14 C13 7.3(5) . . . . ?
C5 N1 N2 C8 -178.5(2) . . . . ?
C5 C4 C3 C2 0.8(4) . . . . ?
C7 C2 C3 C4 -2.0(4) . . . . ?
C8 C9 C10 C11 -175.8(3) . . . . ?
C11 C16 C15 C14 0.1(4) . . . . ?
C11 C12 C13 C14 0.9(4) . . . . ?
C16 C11 C10 C9 178.5(3) . . . . ?
C16 C11 C12 C13 -2.2(4) . . . . ?
C16 C15 C14 N3 177.4(3) . . . . ?
C16 C15 C14 C13 -1.4(5) . . . . ?
C2 C7 C6 C5 0.2(4) . . . . ?
C4 C5 C6 C7 -1.4(4) . . . . ?
O3 N3 C14 C15 9.0(5) . . . . ?
O3 N3 C14 C13 -172.1(3) . . . . ?
C6 C5 C4 C3 0.9(4) . . . . ?
C6 C7 C2 O1 -178.7(3) . . . . ?
C6 C7 C2 C3 1.5(4) . . . . ?
C10 C11 C16 C15 -175.4(3) . . . . ?
C10 C11 C12 C13 174.8(3) . . . . ?
C12 C11 C16 C15 1.7(4) . . . . ?
C12 C11 C10 C9 1.5(4) . . . . ?
C12 C13 C14 N3 -177.9(3) . . . . ?
C12 C13 C14 C15 1.0(5) . . . . ?
C1 O1 C2 C7 3.2(4) . . . . ?
C1 O1 C2 C3 -176.9(2) . . . . ?

_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 1.518
_oxdiff_exptl_absorpt_empirical_full_min 0.778
####################################################################### 
# 
# 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_ps_dok98_1b
_database_code_depnum_ccdc_archive 'CCDC 2350543'
loop_
_audit_author_name
_audit_author_address
'Paulina Sobczak'
;Lodz University of Technology
Poland
;
_audit_update_record             
;
2024-04-23 deposited with the CCDC.	2025-01-10 downloaded from the CCDC.
;
_audit_creation_date             2024-01-10
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H15 Br N2 O'
_chemical_formula_sum            'C15 H15 Br N2 O'
_chemical_formula_weight         319.20
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C15 H15 Br N2 O1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.30400(10)
_cell_length_b                   8.79880(10)
_cell_length_c                   29.2208(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1363.70(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10212
_cell_measurement_temperature    100.02(10)
_cell_measurement_theta_max      78.4780
_cell_measurement_theta_min      2.9970
_shelx_estimated_absorpt_T_max   0.895
_shelx_estimated_absorpt_T_min   0.488
_exptl_absorpt_coefficient_mu    4.050
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82638
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.96a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.555
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             648
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -19 0.0064
0 0 19 0.0225
-3 0 -2 0.0870
0 -6 0 0.0076
0 6 0 0.0199
3 -1 5 0.1019
0 4 15 0.0210

_exptl_crystal_size_max          0.207
_exptl_crystal_size_mid          0.031
_exptl_crystal_size_min          0.028
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0195 -0.4252 -18.9123 -0.8475 0.2983 0.4390
0.0454 0.4182 18.9127 0.8396 -0.2954 -0.4559
-3.4221 0.3284 -1.7666 0.3416 -0.1227 0.9318
-0.0414 -5.7108 -0.3103 -0.4297 -0.9029 -0.0091
0.0414 5.7108 0.3103 0.4297 0.9029 0.0091
3.1955 -1.3833 5.3536 -0.2389 -0.1277 -0.9626
-0.0986 3.5521 14.8399 0.9119 0.2717 -0.3076

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            13843
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.672
_diffrn_reflns_theta_min         3.025
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.02(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 300K'
_diffrn_measured_fraction_theta_full 1.000
_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   -120.00 -33.00   0.50    1.00    --  -48.87 -57.00 -60.00  174
  2  ω    -20.00  27.00   0.50    1.00    --  -48.87  19.00-150.00   94
  3  ω    -41.00  27.00   0.50    1.00    --  -48.87  38.00-120.00  136
  4  ω    -27.00  20.00   0.50    1.00    --   48.87 -19.00  30.00   94
  5  ω    -27.00  20.00   0.50    1.00    --   48.87 -19.00 -30.00   94
  6  ω   -164.00 -75.00   0.50    2.00    --  -88.50 -38.00  30.00  178
  7  ω    -66.00 -17.00   0.50    2.00    --  -88.50  57.00 -90.00   98
  8  ω    -66.00 -17.00   0.50    2.00    --  -88.50  57.00  30.00   98
  9  ω    -41.00 -13.00   0.50    2.00    --  -88.50  38.00  90.00   56
 10  ω    -66.00 -17.00   0.50    2.00    --  -88.50  57.00 -30.00   98
 11  ω    -41.00 -13.00   0.50    2.00    --  -88.50  38.00   0.00   56
 12  ω     45.00 134.00   0.50    2.00    --  110.00 -77.00  30.00  178
 13  ω     41.00 106.00   0.50    2.00    --  110.00 -99.00   0.00  130
 14  ω     38.00  66.00   0.50    2.00    --  110.00 -57.00  90.00   56
 15  ω     38.00  66.00   0.50    2.00    --  110.00 -57.00  60.00   56
 16  ω     38.00  66.00   0.50    2.00    --  110.00 -57.00 120.00   56
 17  ω     38.00  66.00   0.50    2.00    --  110.00 -57.00 150.00   56
 18  ω     38.00  66.00   0.50    2.00    --  110.00 -57.00 -30.00   56
 19  ω     38.00 178.00   0.50    2.00    --  110.00   0.00 -60.00  280
 20  ω     97.00 178.00   0.50    2.00    --  110.00  19.00-180.00  162
 21  ω   -114.00 -25.00   0.50    1.00    --  -48.87 -77.00-180.00  178
 22  ω   -120.00 -33.00   0.50    1.00    --  -48.87 -57.00  90.00  174
 23  ω     25.00 114.00   0.50    1.00    --   48.87  77.00-120.00  178
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1149456000
_diffrn_orient_matrix_UB_12      0.0737386000
_diffrn_orient_matrix_UB_13      0.0430365000
_diffrn_orient_matrix_UB_21      0.0610416000
_diffrn_orient_matrix_UB_22      0.1587141000
_diffrn_orient_matrix_UB_23      -0.0192766000
_diffrn_orient_matrix_UB_31      -0.2596571000
_diffrn_orient_matrix_UB_32      0.0047538000
_diffrn_orient_matrix_UB_33      -0.0235890000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.651
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.930
_reflns_number_gt                2770
_reflns_number_total             2847
_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 1.171.42.96a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 
;
 Flack x determined using 1075 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.022(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2847
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0218
_refine_ls_R_factor_gt           0.0209
_refine_ls_restrained_S_all      1.042
_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)+(0.0205P)²+0.9103P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0507
_refine_ls_wR_factor_ref         0.0511
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C10(H10), C6(H6), C13(H13), C11(H11), C4(H4), C14(H14)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C15(H15A,H15B,H15C)
;
_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
Br1 Br 0.62694(7) 0.38435(3) 0.46386(2) 0.02686(9) Uani 1 1 d . . . . .
O1 O 1.1211(4) 0.7498(2) 0.86558(6) 0.0225(4) Uani 1 1 d . . . . .
N1 N 0.5297(5) 0.8252(3) 0.70999(8) 0.0190(5) Uani 1 1 d . . . . .
H1 H 0.396(7) 0.881(4) 0.7137(10) 0.023 Uiso 1 1 d . U . . .
N2 N 0.5666(4) 0.7431(2) 0.67114(7) 0.0170(5) Uani 1 1 d . . . . .
C3 C 1.0277(5) 0.6717(3) 0.78679(9) 0.0177(5) Uani 1 1 d . . . . .
H3 H 1.157403 0.597207 0.786692 0.021 Uiso 1 1 calc R U . . .
C7 C 0.8034(5) 0.8732(3) 0.82468(8) 0.0184(5) Uani 1 1 d . . . . .
H7 H 0.779481 0.936306 0.850694 0.022 Uiso 1 1 calc R U . . .
C9 C 0.4590(5) 0.6696(3) 0.59591(9) 0.0163(5) Uani 1 1 d . . . . .
C1 C 1.3199(5) 0.6421(3) 0.86784(9) 0.0213(6) Uani 1 1 d . . . . .
H1A H 1.442082 0.662815 0.843477 0.032 Uiso 1 1 calc R U . . .
H1B H 1.251141 0.539487 0.863950 0.032 Uiso 1 1 calc R U . . .
H1C H 1.403598 0.649530 0.897649 0.032 Uiso 1 1 calc R U . . .
C12 C 0.5602(5) 0.5006(3) 0.51742(9) 0.0201(6) Uani 1 1 d . . . . .
C8 C 0.4052(5) 0.7576(3) 0.63815(8) 0.0158(5) Uani 1 1 d . . . . .
C5 C 0.6860(5) 0.8005(3) 0.74800(9) 0.0165(5) Uani 1 1 d . . . . .
C2 C 0.9898(5) 0.7622(3) 0.82534(9) 0.0175(5) Uani 1 1 d . . . . .
C10 C 0.6591(6) 0.5665(3) 0.59451(9) 0.0211(6) Uani 1 1 d . . . . .
H10 H 0.762388 0.553904 0.620803 0.025 Uiso 1 1 calc R U . . .
C6 C 0.6524(5) 0.8928(3) 0.78651(8) 0.0184(5) Uani 1 1 d . . . . .
H6 H 0.525617 0.969060 0.786463 0.022 Uiso 1 1 calc R U . . .
C15 C 0.1744(5) 0.8557(3) 0.64144(9) 0.0204(6) Uani 1 1 d . . . . .
H15A H 0.090408 0.837647 0.670819 0.031 Uiso 1 1 calc R U . . .
H15B H 0.058715 0.830684 0.616395 0.031 Uiso 1 1 calc R U . . .
H15C H 0.223252 0.962883 0.639261 0.031 Uiso 1 1 calc R U . . .
C13 C 0.3598(6) 0.6018(3) 0.51736(9) 0.0257(6) Uani 1 1 d . . . . .
H13 H 0.257067 0.613185 0.490944 0.031 Uiso 1 1 calc R U . . .
C11 C 0.7101(6) 0.4820(3) 0.55548(10) 0.0236(6) Uani 1 1 d . . . . .
H11 H 0.846676 0.412218 0.555022 0.028 Uiso 1 1 calc R U . . .
C4 C 0.8747(6) 0.6907(3) 0.74832(8) 0.0181(5) Uani 1 1 d . . . . .
H4 H 0.899649 0.628307 0.722185 0.022 Uiso 1 1 calc R U . . .
C14 C 0.3119(5) 0.6858(3) 0.55647(10) 0.0237(6) Uani 1 1 d . . . . .
H14 H 0.175931 0.756109 0.556524 0.028 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
Br1 C12 1.903(3) . ?
O1 C1 1.419(3) . ?
O1 C2 1.371(3) . ?
N1 H1 0.87(4) . ?
N1 N2 1.360(3) . ?
N1 C5 1.403(3) . ?
N2 C8 1.296(3) . ?
C3 H3 0.9500 . ?
C3 C2 1.394(4) . ?
C3 C4 1.397(4) . ?
C7 H7 0.9500 . ?
C7 C2 1.390(4) . ?
C7 C6 1.384(4) . ?
C9 C8 1.485(4) . ?
C9 C10 1.397(4) . ?
C9 C14 1.399(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C12 C13 1.386(4) . ?
C12 C11 1.377(4) . ?
C8 C15 1.501(4) . ?
C5 C6 1.399(4) . ?
C5 C4 1.390(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.388(4) . ?
C6 H6 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C13 H13 0.9500 . ?
C13 C14 1.385(4) . ?
C11 H11 0.9500 . ?
C4 H4 0.9500 . ?
C14 H14 0.9500 . ?

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
C2 O1 C1 118.1(2) . . ?
N2 N1 H1 121(2) . . ?
N2 N1 C5 119.6(2) . . ?
C5 N1 H1 118(2) . . ?
C8 N2 N1 118.3(2) . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.9(3) . . ?
C4 C3 H3 120.1 . . ?
C2 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C6 C7 C2 120.7(2) . . ?
C10 C9 C8 120.6(2) . . ?
C10 C9 C14 117.8(2) . . ?
C14 C9 C8 121.6(2) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C13 C12 Br1 119.1(2) . . ?
C11 C12 Br1 119.5(2) . . ?
C11 C12 C13 121.3(3) . . ?
N2 C8 C9 116.1(2) . . ?
N2 C8 C15 123.2(2) . . ?
C9 C8 C15 120.7(2) . . ?
C6 C5 N1 118.1(2) . . ?
C4 C5 N1 122.6(2) . . ?
C4 C5 C6 119.3(2) . . ?
O1 C2 C3 125.0(3) . . ?
O1 C2 C7 115.4(2) . . ?
C7 C2 C3 119.5(2) . . ?
C9 C10 H10 119.3 . . ?
C11 C10 C9 121.3(3) . . ?
C11 C10 H10 119.3 . . ?
C7 C6 C5 120.1(3) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C8 C15 H15A 109.5 . . ?
C8 C15 H15B 109.5 . . ?
C8 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C12 C13 H13 120.6 . . ?
C14 C13 C12 118.8(2) . . ?
C14 C13 H13 120.6 . . ?
C12 C11 C10 119.2(3) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.5(2) . . ?
C5 C4 H4 119.8 . . ?
C9 C14 H14 119.2 . . ?
C13 C14 C9 121.5(3) . . ?
C13 C14 H14 119.2 . . ?

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
Br1 C12 C13 C14 179.9(2) . . . . ?
Br1 C12 C11 C10 -179.6(2) . . . . ?
N1 N2 C8 C9 177.9(2) . . . . ?
N1 N2 C8 C15 -2.5(4) . . . . ?
N1 C5 C6 C7 -179.5(2) . . . . ?
N1 C5 C4 C3 179.2(3) . . . . ?
N2 N1 C5 C6 176.4(2) . . . . ?
N2 N1 C5 C4 -2.2(4) . . . . ?
C9 C10 C11 C12 0.1(4) . . . . ?
C1 O1 C2 C3 3.4(4) . . . . ?
C1 O1 C2 C7 -177.8(2) . . . . ?
C12 C13 C14 C9 -0.7(5) . . . . ?
C8 C9 C10 C11 179.2(3) . . . . ?
C8 C9 C14 C13 -178.9(3) . . . . ?
C5 N1 N2 C8 173.5(2) . . . . ?
C2 C3 C4 C5 0.6(4) . . . . ?
C2 C7 C6 C5 0.0(4) . . . . ?
C10 C9 C8 N2 6.2(4) . . . . ?
C10 C9 C8 C15 -173.4(3) . . . . ?
C10 C9 C14 C13 0.7(4) . . . . ?
C6 C7 C2 O1 -177.7(2) . . . . ?
C6 C7 C2 C3 1.2(4) . . . . ?
C6 C5 C4 C3 0.6(4) . . . . ?
C13 C12 C11 C10 -0.1(4) . . . . ?
C11 C12 C13 C14 0.4(4) . . . . ?
C4 C3 C2 O1 177.3(3) . . . . ?
C4 C3 C2 C7 -1.5(4) . . . . ?
C4 C5 C6 C7 -0.9(4) . . . . ?
C14 C9 C8 N2 -174.2(3) . . . . ?
C14 C9 C8 C15 6.2(4) . . . . ?
C14 C9 C10 C11 -0.4(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 1.618
_oxdiff_exptl_absorpt_empirical_full_min 0.742
####################################################################### 
# 
# 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_ps_dok69
_database_code_depnum_ccdc_archive 'CCDC 2350551'
loop_
_audit_author_name
_audit_author_address
'Paulina Sobczak'
;Lodz University of Technology
Poland
;
_audit_update_record             
;
2024-04-23 deposited with the CCDC.	2025-01-10 downloaded from the CCDC.
;
_audit_creation_date             2023-12-07
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H12 Cl2 N2 O'
_chemical_formula_sum            'C14 H12 Cl2 N2 O'
_chemical_formula_weight         295.16
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C14 H12 N2 O1 Cl2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   4.61560(10)
_cell_length_b                   9.49270(10)
_cell_length_c                   30.1240(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.5470(10)
_cell_angle_gamma                90
_cell_volume                     1317.34(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10469
_cell_measurement_temperature    99.9(5)
_cell_measurement_theta_max      79.2640
_cell_measurement_theta_min      2.9230
_shelx_estimated_absorpt_T_max   0.811
_shelx_estimated_absorpt_T_min   0.302
_exptl_absorpt_coefficient_mu    4.371
_exptl_absorpt_correction_T_max  0.836
_exptl_absorpt_correction_T_min  0.335
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.68a (Rigaku Oxford Diffraction, 2022)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             608
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 3 17 0.0412
0 -3 -17 0.0383
3 0 1 0.1680
-3 0 1 0.1898
0 -5 10 0.0266
0 5 -11 0.0219
0 6 7 0.0266
0 -6 -7 0.0324

_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0753 3.1781 16.6825 0.1447 0.6121 0.7774
0.1093 -3.1910 -16.7241 -0.1556 -0.6575 -0.7372
2.9712 0.1597 1.2545 -0.1591 -0.6585 0.7355
-2.9928 0.2704 0.9987 0.1805 0.7488 -0.6378
-0.0726 -5.2032 10.4753 -0.9722 0.2324 0.0266
0.0575 5.1842 -10.5673 0.9720 -0.2324 -0.0343
-0.0435 5.7397 7.1148 0.7171 0.3888 0.5785
0.1697 -5.7977 -6.5890 -0.7426 -0.4028 -0.5351

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_unetI/netI     0.0176
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            13626
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.429
_diffrn_reflns_theta_min         2.939
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(5)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 300K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -27.00  20.00   0.50    0.25    --   48.87 -19.00 120.00   94
  2  ω    -27.00  20.00   0.50    0.25    --   48.87 -19.00   0.00   94
  3  ω    -27.00  20.00   0.50    0.25    --   48.87 -19.00 -60.00   94
  4  ω     41.00 113.00   0.50    0.50    --  110.00-125.00-150.00  144
  5  ω     41.00 113.00   0.50    0.50    --  110.00-125.00-120.00  144
  6  ω     41.00 106.00   0.50    0.50    --  110.00 -99.00 120.00  130
  7  ω     38.00  66.00   0.50    0.50    --  110.00 -57.00  30.00   56
  8  ω     38.00  66.00   0.50    0.50    --  110.00 -57.00  90.00   56
  9  ω     38.00  66.00   0.50    0.50    --  110.00 -57.00 -30.00   56
 10  ω     38.00  66.00   0.50    0.50    --  110.00 -57.00 -60.00   56
 11  ω     38.00  66.00   0.50    0.50    --  110.00 -57.00-150.00   56
 12  ω     25.00 114.00   0.50    0.25    --   48.87  77.00-120.00  178
 13  ω    -41.00  27.00   0.50    0.25    --  -48.87  38.00-150.00  136
 14  ω    -20.00  27.00   0.50    0.25    --  -48.87  19.00 -90.00   94
 15  ω     25.00  76.00   0.50    0.25    --   48.87  77.00 -30.00  102
 16  ω     86.00 176.00   0.50    0.50    --  110.00  77.00 -30.00  180
 17  ω    -20.00  27.00   0.50    0.25    --  -48.87  19.00 150.00   94
 18  ω   -160.00 -16.00   0.50    0.50    --  -88.50   0.00   0.00  288
 19  ω    -41.00 -13.00   0.50    0.50    --  -88.50  38.00  90.00   56
 20  ω    -41.00 -13.00   0.50    0.50    --  -88.50  38.00 -30.00   56
 21  ω    -41.00 -13.00   0.50    0.50    --  -88.50  38.00 -60.00   56
 22  ω    -41.00 -13.00   0.50    0.50    --  -88.50  38.00 -90.00   56
 23  ω    -41.00 -13.00   0.50    0.50    --  -88.50  38.00-180.00   56
 24  ω    -41.00 -13.00   0.50    0.50    --  -88.50  38.00 120.00   56
 25  ω    -41.00 -13.00   0.50    0.50    --  -88.50  38.00 150.00   56
 26  ω   -114.00 -25.00   0.50    0.25    --  -48.87 -77.00 150.00  178
 27  ω    -87.00 -19.00   0.50    0.50    --  -88.50 125.00-180.00  136
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0533462000
_diffrn_orient_matrix_UB_12      0.1485625000
_diffrn_orient_matrix_UB_13      -0.0193904000
_diffrn_orient_matrix_UB_21      -0.2369152000
_diffrn_orient_matrix_UB_22      0.0250466000
_diffrn_orient_matrix_UB_23      0.0329886000
_diffrn_orient_matrix_UB_31      0.2299246000
_diffrn_orient_matrix_UB_32      0.0602920000
_diffrn_orient_matrix_UB_33      0.0340786000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2584
_reflns_number_total             2694
_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 1.171.42.68a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.68a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.68a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2694
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0249
_refine_ls_R_factor_gt           0.0240
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0344P)²+0.4026P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0659
_refine_ls_wR_factor_ref         0.0664
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C13(H13), C3(H3), C4(H4), C8(H8), C10(H10), C11(H11), C7(H7), C6(H6)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_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
Cl2 Cl 0.88327(6) 0.52561(3) 0.56348(2) 0.02257(9) Uani 1 1 d . . . . .
Cl1 Cl 0.27119(7) 0.12895(3) 0.47249(2) 0.02706(10) Uani 1 1 d . . . . .
O1 O -0.11887(19) 0.39151(9) 0.86743(3) 0.02387(19) Uani 1 1 d . . . . .
N2 N 0.4068(2) 0.41039(10) 0.67643(3) 0.0187(2) Uani 1 1 d . . . . .
N1 N 0.4608(2) 0.48912(11) 0.71363(3) 0.0206(2) Uani 1 1 d . . . . .
H1 H 0.625(3) 0.5305(16) 0.7181(5) 0.025 Uiso 1 1 d . U . . .
C9 C 0.5202(2) 0.34570(12) 0.60340(4) 0.0171(2) Uani 1 1 d . . . . .
C14 C 0.6423(2) 0.38453(11) 0.56382(4) 0.0171(2) Uani 1 1 d . . . . .
C5 C 0.3063(2) 0.45969(12) 0.75133(4) 0.0178(2) Uani 1 1 d . . . . .
C13 C 0.5712(2) 0.31834(12) 0.52363(4) 0.0196(2) Uani 1 1 d . . . . .
H13 H 0.656342 0.347324 0.497210 0.023 Uiso 1 1 calc R U . . .
C3 C -0.0365(2) 0.32238(12) 0.79090(4) 0.0190(2) Uani 1 1 d . . . . .
H3 H -0.168883 0.245891 0.791580 0.023 Uiso 1 1 calc R U . . .
C4 C 0.1113(2) 0.34815(12) 0.75268(4) 0.0187(2) Uani 1 1 d . . . . .
H4 H 0.078638 0.289119 0.727397 0.022 Uiso 1 1 calc R U . . .
C8 C 0.5820(2) 0.42206(12) 0.64518(4) 0.0191(2) Uani 1 1 d . . . . .
H8 H 0.749975 0.479623 0.649092 0.023 Uiso 1 1 calc R U . . .
C2 C 0.0099(2) 0.40874(12) 0.82805(4) 0.0188(2) Uani 1 1 d . . . . .
C10 C 0.3254(2) 0.23182(12) 0.60104(4) 0.0195(2) Uani 1 1 d . . . . .
H10 H 0.241987 0.201014 0.627405 0.023 Uiso 1 1 calc R U . . .
C12 C 0.3730(3) 0.20904(12) 0.52295(4) 0.0199(2) Uani 1 1 d . . . . .
C11 C 0.2517(3) 0.16340(12) 0.56149(4) 0.0212(2) Uani 1 1 d . . . . .
H11 H 0.120182 0.086342 0.560658 0.025 Uiso 1 1 calc R U . . .
C7 C 0.2021(3) 0.52169(12) 0.82638(4) 0.0207(2) Uani 1 1 d . . . . .
H7 H 0.232575 0.581632 0.851484 0.025 Uiso 1 1 calc R U . . .
C6 C 0.3486(2) 0.54730(12) 0.78858(4) 0.0198(2) Uani 1 1 d . . . . .
H6 H 0.478687 0.624708 0.787853 0.024 Uiso 1 1 calc R U . . .
C1 C -0.3006(3) 0.27105(13) 0.87113(4) 0.0252(3) Uani 1 1 d . . . . .
H1A H -0.464967 0.277183 0.849006 0.038 Uiso 1 1 calc R U . . .
H1B H -0.373010 0.267692 0.901020 0.038 Uiso 1 1 calc R U . . .
H1C H -0.188800 0.185517 0.865913 0.038 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
Cl2 C14 1.7412(11) . ?
Cl1 C12 1.7382(12) . ?
O1 C2 1.3691(14) . ?
O1 C1 1.4267(15) . ?
N2 N1 1.3571(14) . ?
N2 C8 1.2830(15) . ?
N1 H1 0.859(16) . ?
N1 C5 1.4058(15) . ?
C9 C14 1.3995(16) . ?
C9 C8 1.4651(16) . ?
C9 C10 1.4049(16) . ?
C14 C13 1.3854(16) . ?
C5 C4 1.3918(16) . ?
C5 C6 1.4007(16) . ?
C13 H13 0.9500 . ?
C13 C12 1.3824(16) . ?
C3 H3 0.9500 . ?
C3 C4 1.3959(16) . ?
C3 C2 1.3930(16) . ?
C4 H4 0.9500 . ?
C8 H8 0.9500 . ?
C2 C7 1.3946(17) . ?
C10 H10 0.9500 . ?
C10 C11 1.3807(16) . ?
C12 C11 1.3891(17) . ?
C11 H11 0.9500 . ?
C7 H7 0.9500 . ?
C7 C6 1.3812(17) . ?
C6 H6 0.9500 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?

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
C2 O1 C1 116.89(9) . . ?
C8 N2 N1 117.81(10) . . ?
N2 N1 H1 119.7(10) . . ?
N2 N1 C5 118.78(10) . . ?
C5 N1 H1 116.9(10) . . ?
C14 C9 C8 122.29(10) . . ?
C14 C9 C10 116.73(10) . . ?
C10 C9 C8 120.95(10) . . ?
C9 C14 Cl2 119.92(9) . . ?
C13 C14 Cl2 117.43(9) . . ?
C13 C14 C9 122.60(10) . . ?
C4 C5 N1 122.39(10) . . ?
C4 C5 C6 119.13(11) . . ?
C6 C5 N1 118.47(10) . . ?
C14 C13 H13 120.8 . . ?
C12 C13 C14 118.31(10) . . ?
C12 C13 H13 120.8 . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 120.06(11) . . ?
C5 C4 C3 120.48(10) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
N2 C8 C9 119.31(10) . . ?
N2 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
O1 C2 C3 124.92(11) . . ?
O1 C2 C7 115.75(10) . . ?
C3 C2 C7 119.33(11) . . ?
C9 C10 H10 119.1 . . ?
C11 C10 C9 121.89(11) . . ?
C11 C10 H10 119.1 . . ?
C13 C12 Cl1 118.95(9) . . ?
C13 C12 C11 121.47(11) . . ?
C11 C12 Cl1 119.57(9) . . ?
C10 C11 C12 118.95(11) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 H11 120.5 . . ?
C2 C7 H7 119.7 . . ?
C6 C7 C2 120.68(11) . . ?
C6 C7 H7 119.7 . . ?
C5 C6 H6 119.8 . . ?
C7 C6 C5 120.31(11) . . ?
C7 C6 H6 119.8 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 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
Cl2 C14 C13 C12 -177.94(9) . . . . ?
Cl1 C12 C11 C10 -177.33(9) . . . . ?
O1 C2 C7 C6 178.71(10) . . . . ?
N2 N1 C5 C4 3.44(16) . . . . ?
N2 N1 C5 C6 -175.75(10) . . . . ?
N1 N2 C8 C9 -176.07(9) . . . . ?
N1 C5 C4 C3 179.73(10) . . . . ?
N1 C5 C6 C7 -179.71(10) . . . . ?
C9 C14 C13 C12 -0.48(17) . . . . ?
C9 C10 C11 C12 -0.27(18) . . . . ?
C14 C9 C8 N2 159.78(11) . . . . ?
C14 C9 C10 C11 -1.57(17) . . . . ?
C14 C13 C12 Cl1 177.70(9) . . . . ?
C14 C13 C12 C11 -1.49(17) . . . . ?
C13 C12 C11 C10 1.87(18) . . . . ?
C3 C2 C7 C6 -0.82(17) . . . . ?
C4 C5 C6 C7 1.07(17) . . . . ?
C4 C3 C2 O1 -178.69(10) . . . . ?
C4 C3 C2 C7 0.79(17) . . . . ?
C8 N2 N1 C5 -168.37(10) . . . . ?
C8 C9 C14 Cl2 1.48(15) . . . . ?
C8 C9 C14 C13 -175.92(11) . . . . ?
C8 C9 C10 C11 176.34(11) . . . . ?
C2 C3 C4 C5 0.16(17) . . . . ?
C2 C7 C6 C5 -0.12(17) . . . . ?
C10 C9 C14 Cl2 179.36(8) . . . . ?
C10 C9 C14 C13 1.96(16) . . . . ?
C10 C9 C8 N2 -18.01(16) . . . . ?
C6 C5 C4 C3 -1.09(17) . . . . ?
C1 O1 C2 C3 3.79(16) . . . . ?
C1 O1 C2 C7 -175.71(10) . . . . ?

_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 1.811
_oxdiff_exptl_absorpt_empirical_full_min 0.451
####################################################################### 
# 
# 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_ps_dok68
_database_code_depnum_ccdc_archive 'CCDC 2350549'
loop_
_audit_author_name
_audit_author_address
'Paulina Sobczak'
;Lodz University of Technology
Poland
;
_audit_update_record             
;
2024-04-23 deposited with the CCDC.	2025-01-10 downloaded from the CCDC.
;
_audit_creation_date             2023-12-07
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H11 N3 O3 S'
_chemical_formula_sum            'C12 H11 N3 O3 S'
_chemical_formula_weight         277.30
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C12 H11 N3 O3 S1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   9.92380(10)
_cell_length_b                   23.4635(3)
_cell_length_c                   11.4920(2)
_cell_angle_alpha                90
_cell_angle_beta                 105.8050(10)
_cell_angle_gamma                90
_cell_volume                     2574.71(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    16933
_cell_measurement_temperature    105(7)
_cell_measurement_theta_max      79.6300
_cell_measurement_theta_min      3.7510
_shelx_estimated_absorpt_T_max   0.854
_shelx_estimated_absorpt_T_min   0.707
_exptl_absorpt_coefficient_mu    2.326
_exptl_absorpt_correction_T_max  0.896
_exptl_absorpt_correction_T_min  0.797
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.68a (Rigaku Oxford Diffraction, 2022)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1152
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
3 -13 -1 0.0390
-4 6 6 0.0551
1 9 -6 0.0373
4 -4 -6 0.0617
0 -8 -6 0.0276
2 7 5 0.0319
1 -14 -3 0.0276
-4 -9 5 0.0691
4 -3 4 0.0323
3 11 2 0.0392
-1 3 -7 0.0255

_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
3.1008 -13.3524 -1.0228 0.0166 0.7133 -0.7007
-4.3692 6.1136 5.7903 0.0027 0.0253 0.9997
1.4372 9.4738 -5.8372 -0.0245 -0.9401 -0.3400
4.3069 -4.3579 -6.2790 -0.0061 -0.1603 -0.9870
-0.3507 -7.8629 -6.0241 0.7116 -0.0945 -0.6962
2.2158 7.1334 5.1449 -0.8827 0.1164 0.4553
1.3057 -13.9874 -2.8511 0.4166 0.5413 -0.7304
-3.8526 -8.5066 5.3335 0.3674 0.7746 0.5148
4.0307 -2.6324 4.1942 -0.7933 0.6077 -0.0385
3.3475 10.8404 2.3400 -0.9319 -0.2775 0.2337
-0.5289 2.8376 -6.8604 0.5042 -0.7338 -0.4553

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            26227
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.321
_diffrn_reflns_theta_min         3.768
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      105(7)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 300K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -72.00  17.00   0.50    1.00    --  -48.87  77.00 -90.00  178
  2  ω    -72.00  17.00   0.50    1.00    --  -48.87  77.00-150.00  178
  3  ω    -72.00  17.00   0.50    1.00    --  -48.87  77.00  90.00  178
  4  ω     25.00 114.00   0.50    1.00    --   48.87  77.00 150.00  178
  5  ω   -112.00 -22.00   0.50    2.00    --  -88.50  77.00  90.00  180
  6  ω   -112.00 -22.00   0.50    2.00    --  -88.50  77.00  60.00  180
  7  ω   -112.00 -22.00   0.50    2.00    --  -88.50  77.00 120.00  180
  8  ω     86.00 176.00   0.50    2.00    --  110.00  77.00  30.00  180
  9  ω     86.00 176.00   0.50    2.00    --  110.00  77.00  60.00  180
 10  ω     86.00 176.00   0.50    2.00    --  110.00  77.00 120.00  180
 11  ω     86.00 176.00   0.50    2.00    --  110.00  77.00   0.00  180
 12  ω     86.00 176.00   0.50    2.00    --  110.00  77.00  90.00  180
 13  ω   -124.00 -89.00   0.50    1.00    --  -48.87 -38.00 -60.00   70
 14  ω     25.00 114.00   0.50    1.00    --   48.87  77.00-150.00  178
 15  ω     33.00 121.00   0.50    1.00    --   48.87  57.00  60.00  176
 16  ω     25.00 114.00   0.50    1.00    --   48.87  77.00 -60.00  178
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1374841000
_diffrn_orient_matrix_UB_12      -0.0274805000
_diffrn_orient_matrix_UB_13      -0.0742562000
_diffrn_orient_matrix_UB_21      0.0301166000
_diffrn_orient_matrix_UB_22      -0.0527717000
_diffrn_orient_matrix_UB_23      0.0828180000
_diffrn_orient_matrix_UB_31      -0.0787452000
_diffrn_orient_matrix_UB_32      0.0277591000
_diffrn_orient_matrix_UB_33      0.0839181000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4808
_reflns_number_total             5353
_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 1.171.42.68a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.68a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.68a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     351
_refine_ls_number_reflns         5353
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0340
_refine_ls_R_factor_gt           0.0307
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0478P)²+0.7416P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0870
_refine_ls_wR_factor_ref         0.0890
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C12(H12), C28(H28), C24(H24), C32(H32), C11(H11), C31(H31), C23(H23),
 C3(H3), C26(H26), C4(H4), C27(H27), C6(H6), C7(H7)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C21(H21A,H21B,H21C)
;
_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
S1 S 0.43743(3) 0.24337(2) 0.04813(3) 0.02202(9) Uani 1 1 d . . . . .
S21 S 0.55708(3) 0.74150(2) 0.46494(3) 0.02196(9) Uani 1 1 d . . . . .
O21 O 0.64355(10) 0.39218(4) 0.29926(8) 0.0268(2) Uani 1 1 d . . . . .
O1 O 0.34479(10) -0.10308(4) 0.16654(9) 0.0298(2) Uani 1 1 d . . . . .
O2 O 0.58691(10) 0.28967(5) -0.11028(9) 0.0347(2) Uani 1 1 d . . . . .
O22 O 0.39467(10) 0.78964(5) 0.61122(9) 0.0342(2) Uani 1 1 d . . . . .
O3 O 0.56772(10) 0.38007(4) -0.07184(9) 0.0343(2) Uani 1 1 d . . . . .
O23 O 0.42182(10) 0.87954(4) 0.57488(10) 0.0362(2) Uani 1 1 d . . . . .
N2 N 0.31418(10) 0.16705(4) 0.19250(9) 0.0208(2) Uani 1 1 d . . . . .
N22 N 0.68837(10) 0.66356(4) 0.32416(9) 0.0209(2) Uani 1 1 d . . . . .
N1 N 0.25851(12) 0.12630(4) 0.24602(10) 0.0228(2) Uani 1 1 d . . . . .
H1 H 0.1990(16) 0.1342(6) 0.2863(14) 0.027 Uiso 1 1 d . U . . .
N21 N 0.73755(12) 0.62438(4) 0.26127(10) 0.0234(2) Uani 1 1 d . . . . .
H21 H 0.7813(16) 0.6344(6) 0.2077(14) 0.028 Uiso 1 1 d . U . . .
N3 N 0.54312(11) 0.32904(5) -0.05812(10) 0.0268(2) Uani 1 1 d . . . . .
N23 N 0.44469(11) 0.82846(5) 0.56220(10) 0.0274(2) Uani 1 1 d . . . . .
C8 C 0.28651(12) 0.21977(5) 0.21004(11) 0.0204(2) Uani 1 1 d . . . . .
H8 H 0.230157 0.229651 0.261863 0.024 Uiso 1 1 calc R U . . .
C12 C 0.33291(13) 0.32141(5) 0.15790(11) 0.0219(2) Uani 1 1 d . . . . .
H12 H 0.283865 0.339501 0.208079 0.026 Uiso 1 1 calc R U . . .
C28 C 0.71231(12) 0.71662(5) 0.30611(11) 0.0208(2) Uani 1 1 d . . . . .
H28 H 0.766791 0.726860 0.252988 0.025 Uiso 1 1 calc R U . . .
C5 C 0.28750(13) 0.06886(5) 0.22813(11) 0.0211(2) Uani 1 1 d . . . . .
C9 C 0.34383(12) 0.26280(5) 0.14857(11) 0.0198(2) Uani 1 1 d . . . . .
C25 C 0.70934(12) 0.56639(5) 0.27357(11) 0.0211(2) Uani 1 1 d . . . . .
C24 C 0.67520(13) 0.54563(5) 0.37562(11) 0.0227(3) Uani 1 1 d . . . . .
H24 H 0.667382 0.571250 0.437467 0.027 Uiso 1 1 calc R U . . .
C2 C 0.33382(14) -0.04562(5) 0.18668(11) 0.0235(3) Uani 1 1 d . . . . .
C32 C 0.66620(13) 0.81825(5) 0.35609(11) 0.0228(3) Uani 1 1 d . . . . .
H32 H 0.717530 0.835762 0.307048 0.027 Uiso 1 1 calc R U . . .
C22 C 0.66264(13) 0.45026(5) 0.29645(11) 0.0218(2) Uani 1 1 d . . . . .
C11 C 0.40207(13) 0.35112(5) 0.08525(11) 0.0233(3) Uani 1 1 d . . . . .
H11 H 0.406737 0.391478 0.080854 0.028 Uiso 1 1 calc R U . . .
C31 C 0.59350(13) 0.84885(5) 0.42447(12) 0.0244(3) Uani 1 1 d . . . . .
H31 H 0.588549 0.889246 0.426955 0.029 Uiso 1 1 calc R U . . .
C29 C 0.65539(12) 0.75971(5) 0.36750(11) 0.0196(2) Uani 1 1 d . . . . .
C10 C 0.46209(13) 0.31423(5) 0.02136(11) 0.0227(3) Uani 1 1 d . . . . .
C30 C 0.53047(13) 0.81268(5) 0.48729(11) 0.0229(3) Uani 1 1 d . . . . .
C23 C 0.65252(13) 0.48776(5) 0.38754(11) 0.0236(3) Uani 1 1 d . . . . .
H23 H 0.630175 0.473823 0.457644 0.028 Uiso 1 1 calc R U . . .
C3 C 0.42155(13) -0.00397(5) 0.16089(11) 0.0242(3) Uani 1 1 d . . . . .
H3 H 0.496817 -0.014479 0.128961 0.029 Uiso 1 1 calc R U . . .
C26 C 0.71776(13) 0.52865(5) 0.18201(11) 0.0239(3) Uani 1 1 d . . . . .
H26 H 0.740240 0.542517 0.111906 0.029 Uiso 1 1 calc R U . . .
C4 C 0.39832(13) 0.05311(5) 0.18216(11) 0.0237(3) Uani 1 1 d . . . . .
H4 H 0.458468 0.081538 0.165205 0.028 Uiso 1 1 calc R U . . .
C27 C 0.69343(13) 0.47104(5) 0.19300(11) 0.0244(3) Uani 1 1 d . . . . .
H27 H 0.697744 0.445601 0.129802 0.029 Uiso 1 1 calc R U . . .
C6 C 0.20145(13) 0.02701(5) 0.25556(12) 0.0251(3) Uani 1 1 d . . . . .
H6 H 0.126989 0.037392 0.288607 0.030 Uiso 1 1 calc R U . . .
C7 C 0.22469(14) -0.02977(5) 0.23456(12) 0.0271(3) Uani 1 1 d . . . . .
H7 H 0.165561 -0.058213 0.253016 0.033 Uiso 1 1 calc R U . . .
C1 C 0.44223(15) -0.12038(6) 0.10241(13) 0.0311(3) Uani 1 1 d . . . . .
H1A H 0.419443 -0.101547 0.023331 0.047 Uiso 1 1 calc R U . . .
H1B H 0.437093 -0.161802 0.091063 0.047 Uiso 1 1 calc R U . . .
H1C H 0.537152 -0.109703 0.148738 0.047 Uiso 1 1 calc R U . . .
C21 C 0.61963(16) 0.36836(6) 0.40620(13) 0.0326(3) Uani 1 1 d . . . . .
H21A H 0.610710 0.326873 0.397559 0.049 Uiso 1 1 calc R U . . .
H21B H 0.533207 0.384215 0.418552 0.049 Uiso 1 1 calc R U . . .
H21C H 0.698537 0.377632 0.475892 0.049 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
S1 C9 1.7282(12) . ?
S1 C10 1.7204(13) . ?
S21 C29 1.7273(12) . ?
S21 C30 1.7212(13) . ?
O21 C22 1.3774(14) . ?
O21 C21 1.4276(16) . ?
O1 C2 1.3772(14) . ?
O1 C1 1.4253(15) . ?
O2 N3 1.2424(15) . ?
O22 N23 1.2434(15) . ?
O3 N3 1.2406(15) . ?
O23 N23 1.2357(15) . ?
N2 N1 1.3352(14) . ?
N2 C8 1.2947(15) . ?
N22 N21 1.3408(14) . ?
N22 C28 1.2948(15) . ?
N1 H1 0.864(16) . ?
N1 C5 1.4049(15) . ?
N21 H21 0.877(16) . ?
N21 C25 1.4042(15) . ?
N3 C10 1.4149(16) . ?
N23 C30 1.4148(16) . ?
C8 H8 0.9500 . ?
C8 C9 1.4355(17) . ?
C12 H12 0.9500 . ?
C12 C9 1.3860(17) . ?
C12 C11 1.4022(17) . ?
C28 H28 0.9500 . ?
C28 C29 1.4337(16) . ?
C5 C4 1.3935(17) . ?
C5 C6 1.3927(17) . ?
C25 C24 1.3942(17) . ?
C25 C26 1.3950(17) . ?
C24 H24 0.9500 . ?
C24 C23 1.3892(17) . ?
C2 C3 1.3934(17) . ?
C2 C7 1.3923(18) . ?
C32 H32 0.9500 . ?
C32 C31 1.4008(17) . ?
C32 C29 1.3867(17) . ?
C22 C23 1.3919(17) . ?
C22 C27 1.3937(17) . ?
C11 H11 0.9500 . ?
C11 C10 1.3716(18) . ?
C31 H31 0.9500 . ?
C31 C30 1.3706(18) . ?
C23 H23 0.9500 . ?
C3 H3 0.9500 . ?
C3 C4 1.3919(17) . ?
C26 H26 0.9500 . ?
C26 C27 1.3850(17) . ?
C4 H4 0.9500 . ?
C27 H27 0.9500 . ?
C6 H6 0.9500 . ?
C6 C7 1.3843(17) . ?
C7 H7 0.9500 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 S1 C9 89.60(6) . . ?
C30 S21 C29 89.62(6) . . ?
C22 O21 C21 117.63(10) . . ?
C2 O1 C1 117.50(10) . . ?
C8 N2 N1 118.72(10) . . ?
C28 N22 N21 117.60(10) . . ?
N2 N1 H1 121.5(10) . . ?
N2 N1 C5 119.52(10) . . ?
C5 N1 H1 118.8(10) . . ?
N22 N21 H21 121.2(10) . . ?
N22 N21 C25 119.89(10) . . ?
C25 N21 H21 118.7(10) . . ?
O2 N3 C10 117.63(11) . . ?
O3 N3 O2 123.34(11) . . ?
O3 N3 C10 119.03(11) . . ?
O22 N23 C30 117.69(11) . . ?
O23 N23 O22 123.25(11) . . ?
O23 N23 C30 119.06(12) . . ?
N2 C8 H8 121.1 . . ?
N2 C8 C9 117.77(11) . . ?
C9 C8 H8 121.1 . . ?
C9 C12 H12 123.6 . . ?
C9 C12 C11 112.71(11) . . ?
C11 C12 H12 123.6 . . ?
N22 C28 H28 120.5 . . ?
N22 C28 C29 119.02(11) . . ?
C29 C28 H28 120.5 . . ?
C4 C5 N1 121.61(11) . . ?
C6 C5 N1 118.74(11) . . ?
C6 C5 C4 119.65(11) . . ?
C8 C9 S1 120.02(9) . . ?
C12 C9 S1 112.39(9) . . ?
C12 C9 C8 127.58(11) . . ?
C24 C25 N21 121.60(11) . . ?
C24 C25 C26 119.41(11) . . ?
C26 C25 N21 118.98(11) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 C25 120.49(11) . . ?
C23 C24 H24 119.8 . . ?
O1 C2 C3 124.62(11) . . ?
O1 C2 C7 115.69(11) . . ?
C7 C2 C3 119.68(11) . . ?
C31 C32 H32 123.5 . . ?
C29 C32 H32 123.5 . . ?
C29 C32 C31 112.94(11) . . ?
O21 C22 C23 124.70(11) . . ?
O21 C22 C27 115.44(11) . . ?
C23 C22 C27 119.86(11) . . ?
C12 C11 H11 124.5 . . ?
C10 C11 C12 111.06(11) . . ?
C10 C11 H11 124.5 . . ?
C32 C31 H31 124.5 . . ?
C30 C31 C32 110.90(11) . . ?
C30 C31 H31 124.5 . . ?
C28 C29 S21 120.82(9) . . ?
C32 C29 S21 112.22(9) . . ?
C32 C29 C28 126.93(11) . . ?
N3 C10 S1 119.10(10) . . ?
C11 C10 S1 114.24(9) . . ?
C11 C10 N3 126.63(12) . . ?
N23 C30 S21 119.13(10) . . ?
C31 C30 S21 114.30(9) . . ?
C31 C30 N23 126.52(12) . . ?
C24 C23 C22 119.80(11) . . ?
C24 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C2 C3 H3 120.2 . . ?
C4 C3 C2 119.64(11) . . ?
C4 C3 H3 120.2 . . ?
C25 C26 H26 119.9 . . ?
C27 C26 C25 120.19(11) . . ?
C27 C26 H26 119.9 . . ?
C5 C4 H4 119.8 . . ?
C3 C4 C5 120.49(11) . . ?
C3 C4 H4 119.8 . . ?
C22 C27 H27 119.9 . . ?
C26 C27 C22 120.23(11) . . ?
C26 C27 H27 119.9 . . ?
C5 C6 H6 120.1 . . ?
C7 C6 C5 119.84(11) . . ?
C7 C6 H6 120.1 . . ?
C2 C7 H7 119.7 . . ?
C6 C7 C2 120.69(12) . . ?
C6 C7 H7 119.7 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O21 C21 H21A 109.5 . . ?
O21 C21 H21B 109.5 . . ?
O21 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
O21 C22 C23 C24 179.39(11) . . . . ?
O21 C22 C27 C26 -178.53(11) . . . . ?
O1 C2 C3 C4 178.32(12) . . . . ?
O1 C2 C7 C6 -178.32(12) . . . . ?
O2 N3 C10 S1 3.75(15) . . . . ?
O2 N3 C10 C11 -178.58(12) . . . . ?
O22 N23 C30 S21 1.68(15) . . . . ?
O22 N23 C30 C31 179.13(12) . . . . ?
O3 N3 C10 S1 -175.79(9) . . . . ?
O3 N3 C10 C11 1.88(19) . . . . ?
O23 N23 C30 S21 -177.57(9) . . . . ?
O23 N23 C30 C31 -0.12(19) . . . . ?
N2 N1 C5 C4 16.32(18) . . . . ?
N2 N1 C5 C6 -162.69(11) . . . . ?
N2 C8 C9 S1 3.76(16) . . . . ?
N2 C8 C9 C12 -177.03(12) . . . . ?
N22 N21 C25 C24 -22.42(18) . . . . ?
N22 N21 C25 C26 158.50(11) . . . . ?
N22 C28 C29 S21 0.38(16) . . . . ?
N22 C28 C29 C32 -177.66(12) . . . . ?
N1 N2 C8 C9 -178.06(10) . . . . ?
N1 C5 C4 C3 -177.51(11) . . . . ?
N1 C5 C6 C7 177.64(12) . . . . ?
N21 N22 C28 C29 177.01(11) . . . . ?
N21 C25 C24 C23 -177.75(11) . . . . ?
N21 C25 C26 C27 178.60(11) . . . . ?
C8 N2 N1 C5 -179.93(11) . . . . ?
C12 C11 C10 S1 -0.38(14) . . . . ?
C12 C11 C10 N3 -178.15(12) . . . . ?
C28 N22 N21 C25 -177.28(11) . . . . ?
C5 C6 C7 C2 0.3(2) . . . . ?
C9 S1 C10 N3 177.83(10) . . . . ?
C9 S1 C10 C11 -0.12(10) . . . . ?
C9 C12 C11 C10 0.84(16) . . . . ?
C25 C24 C23 C22 -0.61(18) . . . . ?
C25 C26 C27 C22 -1.05(19) . . . . ?
C24 C25 C26 C27 -0.50(19) . . . . ?
C2 C3 C4 C5 -0.48(19) . . . . ?
C32 C31 C30 S21 -0.17(14) . . . . ?
C32 C31 C30 N23 -177.72(12) . . . . ?
C11 C12 C9 S1 -0.94(14) . . . . ?
C11 C12 C9 C8 179.80(12) . . . . ?
C31 C32 C29 S21 -0.90(14) . . . . ?
C31 C32 C29 C28 177.28(12) . . . . ?
C29 S21 C30 N23 177.47(10) . . . . ?
C29 S21 C30 C31 -0.28(10) . . . . ?
C29 C32 C31 C30 0.68(16) . . . . ?
C10 S1 C9 C8 179.93(10) . . . . ?
C10 S1 C9 C12 0.60(10) . . . . ?
C30 S21 C29 C28 -177.65(10) . . . . ?
C30 S21 C29 C32 0.66(10) . . . . ?
C23 C22 C27 C26 1.77(19) . . . . ?
C3 C2 C7 C6 0.7(2) . . . . ?
C26 C25 C24 C23 1.33(18) . . . . ?
C4 C5 C6 C7 -1.40(19) . . . . ?
C27 C22 C23 C24 -0.94(18) . . . . ?
C6 C5 C4 C3 1.50(19) . . . . ?
C7 C2 C3 C4 -0.63(19) . . . . ?
C1 O1 C2 C3 -7.47(18) . . . . ?
C1 O1 C2 C7 171.52(12) . . . . ?
C21 O21 C22 C23 -3.78(18) . . . . ?
C21 O21 C22 C27 176.54(12) . . . . ?

_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 1.321
_oxdiff_exptl_absorpt_empirical_full_min 0.759
####################################################################### 
# 
# 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_ps_dok57a
_database_code_depnum_ccdc_archive 'CCDC 2350546'
loop_
_audit_author_name
_audit_author_address
'Paulina Sobczak'
;Lodz University of Technology
Poland
;
_audit_update_record             
;
2024-04-23 deposited with the CCDC.	2025-01-10 downloaded from the CCDC.
;
_audit_creation_date             2023-12-19
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H19 N3 O'
_chemical_formula_sum            'C16 H19 N3 O'
_chemical_formula_weight         269.34
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C16 H19 N3 O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   11.95080(10)
_cell_length_b                   7.29470(10)
_cell_length_c                   16.1641(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.8960(10)
_cell_angle_gamma                90
_cell_volume                     1395.79(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    16751
_cell_measurement_temperature    100.01(13)
_cell_measurement_theta_max      79.1190
_cell_measurement_theta_min      2.7560
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.854
_exptl_absorpt_coefficient_mu    0.652
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.917
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.96a (Rigaku Oxford Diffraction, 2023)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             576
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
7 0 -7 0.0138
-7 0 7 0.0038
-4 0 -8 0.0203
4 0 8 0.0123
-1 5 1 0.1094
1 -5 -1 0.1314
-4 3 -5 0.0764

_exptl_crystal_size_max          0.251
_exptl_crystal_size_mid          0.033
_exptl_crystal_size_min          0.018
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
6.6314 -0.0635 -6.6159 0.8706 -0.4138 -0.2662
-6.6314 0.0635 6.6159 -0.8706 0.4138 0.2662
-3.6654 0.0125 -8.4803 0.4216 0.8853 -0.1963
3.6654 -0.0125 8.4803 -0.4216 -0.8853 0.1963
-1.3512 4.6300 1.4698 0.1125 0.1435 0.9832
1.3512 -4.6300 -1.4698 -0.1125 -0.1435 -0.9832
-4.0000 3.0000 -5.0000 0.3365 0.7784 0.5033

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_Laue_measured_fraction_full 1.000
_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       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            27539
_diffrn_reflns_point_group_measured_fraction_full 0.868
_diffrn_reflns_point_group_measured_fraction_max 0.805
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.440
_diffrn_reflns_theta_min         2.760
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(13)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 300K'
_diffrn_measured_fraction_theta_full 1.000
_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   -121.00 -75.00   0.50    4.00    --  -49.12   0.00-180.00   92
  2  ω   -121.00 -75.00   0.50    4.00    --  -49.12   0.00 120.00   92
  3  ω    -41.00  26.00   0.50    4.00    --  -49.12  38.00  90.00  134
  4  ω    -19.00  27.00   0.50    4.00    --  -49.12  19.00 -30.00   92
  5  ω   -121.00 -75.00   0.50    4.00    --  -49.12   0.00-120.00   92
  6  ω   -121.00 -75.00   0.50    4.00    --  -49.12   0.00 150.00   92
  7  ω     62.00 120.00   0.50    4.00    --   49.12 178.00-150.00  116
  8  ω    -27.00  19.00   0.50    4.00    --   49.12 -19.00-120.00   92
  9  ω     60.00 122.00   0.50    4.00    --   49.12-178.00  30.00  124
 10  ω    -41.00 -13.00   0.50   20.00    --  -88.50  38.00 120.00   56
 11  ω   -112.00 -22.00   0.50   20.00    --  -88.50  77.00   0.00  180
 12  ω   -164.00 -75.00   0.50   20.00    --  -88.50 -19.00 120.00  178
 13  ω    -41.00 -13.00   0.50   20.00    --  -88.50  38.00 -60.00   56
 14  ω   -112.00 -22.00   0.50   20.00    --  -88.50  77.00  90.00  180
 15  ω    -41.00 -13.00   0.50   20.00    --  -88.50  38.00   0.00   56
 16  ω   -157.00 -69.00   0.50   20.00    --  -88.50 -67.00 -63.57  176
 17  ω   -160.00 -75.00   0.50   20.00    --  -88.50   0.00-180.00  170
 18  ω    -66.00 -17.00   0.50   20.00    --  -88.50  57.00  90.00   98
 19  ω   -112.00 -22.00   0.50   20.00    --  -88.50  77.00 -90.00  180
 20  ω   -157.00 -69.00   0.50   20.00    --  -88.50 -67.00 -63.57  176
 21  ω     38.00  66.00   0.50   20.00    --  110.00 -57.00-180.00   56
 22  ω     38.00  66.00   0.50   20.00    --  110.00 -57.00 120.00   56
 23  ω    105.00 178.00   0.50   20.00    --  110.00   0.00-180.00  146
 24  ω     41.00 113.00   0.50   20.00    --  110.00-125.00-180.00  144
 25  ω     41.00 113.00   0.50   20.00    --  110.00-125.00-180.00  144
 26  ω     38.00  66.00   0.50   20.00    --  110.00 -57.00 -60.00   56
 27  ω     38.00  66.00   0.50   20.00    --  110.00 -57.00   0.00   56
 28  ω     38.00  66.00   0.50   20.00    --  110.00 -57.00 -90.00   56
 29  ω     41.00 113.00   0.50   20.00    --  110.00-125.00 -30.00  144
 30  ω     41.00  77.00   0.50   20.00    --  110.00 -99.00 -90.00   72
 31  ω     38.00  66.00   0.50   20.00    --  110.00 -57.00 150.00   56
 32  ω     41.00 113.00   0.50   20.00    --  110.00-125.00 150.00  144
 33  ω     41.00 113.00   0.50   20.00    --  110.00-125.00  60.00  144
 34  ω     41.00 113.00   0.50   20.00    --  110.00-125.00  60.00  144
 35  ω     38.00  66.00   0.50   20.00    --  110.00 -57.00-120.00   56
 36  ω     97.00 178.00   0.50   20.00    --  110.00  19.00-120.00  162
 37  ω     41.00 106.00   0.50   20.00    --  110.00 -99.00-180.00  130
 38  ω     38.00  66.00   0.50   20.00    --  110.00 -57.00-150.00   56
 39  ω     86.00 176.00   0.50   20.00    --  110.00  77.00-180.00  180
 40  ω     86.00 176.00   0.50   20.00    --  110.00  77.00-180.00  180
 41  ω   -121.00 -75.00   0.50    4.00    --  -49.12   0.00 -60.00   92
 42  ω   -114.00 -41.00   0.50    4.00    --  -49.12 -77.00  60.00  146
 43  ω     26.00 114.00   0.50    4.00    --   49.12  77.00   0.00  176
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0575727000
_diffrn_orient_matrix_UB_12      0.0647449000
_diffrn_orient_matrix_UB_13      -0.0745037000
_diffrn_orient_matrix_UB_21      -0.1162595000
_diffrn_orient_matrix_UB_22      0.0142460000
_diffrn_orient_matrix_UB_23      -0.0541228000
_diffrn_orient_matrix_UB_31      -0.0103689000
_diffrn_orient_matrix_UB_32      0.2004747000
_diffrn_orient_matrix_UB_33      0.0279187000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.524
_reflns_Friedel_fraction_full    0.710
_reflns_Friedel_fraction_max     0.602
_reflns_number_gt                4628
_reflns_number_total             4881
_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 1.171.42.96a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 
;
 Flack x determined using 1500 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(14)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     373
_refine_ls_number_reflns         4881
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0351
_refine_ls_restrained_S_all      1.067
_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)+(0.0561P)²+0.3238P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0937
_refine_ls_wR_factor_ref         0.0990
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C11(H11), C8(H8), C24(H24), C3(H3), C10(H10), C13(H13), C14(H14),
 C26(H26), C30(H30), C31(H31), C4(H4), C34(H34), C6(H6), C23(H23), C28(H28),
 C27(H27), C33(H33)
2.b Idealised Me refined as rotating group:
 C15(H15a,H15b,H15c), C16(H16a,H16b,H16c), C1(H1a,H1b,H1c), C36(H36a,H36b,
 H36c), C35(H35a,H35b,H35c), C21(H21a,H21b,H21c)
;
_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
O1 O 0.75809(12) 0.4883(2) 0.25700(9) 0.0236(4) Uani 1 1 d . . . . .
O21 O -0.00439(12) 0.4834(3) 0.67223(9) 0.0264(4) Uani 1 1 d . . . . .
N2 N 0.55336(14) 0.5189(3) 0.60282(10) 0.0184(4) Uani 1 1 d . . . . .
N22 N 0.20680(15) 0.5264(3) 0.33188(11) 0.0214(4) Uani 1 1 d . . . . .
N1 N 0.50609(15) 0.5502(3) 0.52156(10) 0.0208(4) Uani 1 1 d . . . . .
H1 H 0.447(2) 0.627(4) 0.5139(16) 0.025 Uiso 1 1 d . U . . .
N3 N 0.61831(14) 0.4662(3) 1.00708(10) 0.0191(4) Uani 1 1 d . . . . .
N23 N 0.09664(15) 0.4927(3) -0.07288(11) 0.0235(4) Uani 1 1 d . . . . .
N21 N 0.25846(15) 0.4959(3) 0.41231(11) 0.0237(4) Uani 1 1 d . . . . .
H21 H 0.308(2) 0.400(4) 0.4212(17) 0.028 Uiso 1 1 d . U . . .
C7 C 0.59624(17) 0.5814(3) 0.31318(12) 0.0194(4) Uani 1 1 d . . . . .
H7 H 0.568634 0.630832 0.259906 0.023 Uiso 1 1 calc R U . . .
C11 C 0.65129(16) 0.4089(3) 0.86394(13) 0.0178(4) Uani 1 1 d . . . . .
H11 H 0.715483 0.336167 0.883379 0.021 Uiso 1 1 calc R U . . .
C9 C 0.52739(16) 0.5407(3) 0.74757(12) 0.0164(4) Uani 1 1 d . . . . .
C12 C 0.58777(16) 0.4887(3) 0.92248(12) 0.0161(4) Uani 1 1 d . . . . .
C29 C 0.21414(17) 0.4780(3) 0.18553(13) 0.0195(4) Uani 1 1 d . . . . .
C8 C 0.49404(16) 0.5752(3) 0.65848(13) 0.0176(4) Uani 1 1 d . . . . .
H8 H 0.426411 0.641363 0.641133 0.021 Uiso 1 1 calc R U . . .
C24 C 0.08443(17) 0.5853(3) 0.46618(13) 0.0206(5) Uani 1 1 d . . . . .
H24 H 0.058430 0.646415 0.415266 0.025 Uiso 1 1 calc R U . . .
C3 C 0.73986(16) 0.4167(3) 0.40270(13) 0.0180(4) Uani 1 1 d . . . . .
H3 H 0.810098 0.353774 0.410916 0.022 Uiso 1 1 calc R U . . .
C10 C 0.62162(16) 0.4349(3) 0.77935(13) 0.0179(4) Uani 1 1 d . . . . .
H10 H 0.665979 0.379804 0.741645 0.021 Uiso 1 1 calc R U . . .
C13 C 0.49138(16) 0.5901(3) 0.89050(12) 0.0176(4) Uani 1 1 d . . . . .
H13 H 0.445400 0.642473 0.927802 0.021 Uiso 1 1 calc R U . . .
C25 C 0.18851(17) 0.4975(3) 0.47597(13) 0.0191(4) Uani 1 1 d . . . . .
C32 C 0.13494(17) 0.4889(3) 0.01137(12) 0.0191(4) Uani 1 1 d . . . . .
C14 C 0.46265(16) 0.6146(3) 0.80509(12) 0.0175(4) Uani 1 1 d . . . . .
H14 H 0.397032 0.683537 0.785162 0.021 Uiso 1 1 calc R U . . .
C26 C 0.22666(17) 0.4111(3) 0.55161(13) 0.0203(4) Uani 1 1 d . . . . .
H26 H 0.298158 0.351955 0.559028 0.024 Uiso 1 1 calc R U . . .
C30 C 0.11796(17) 0.5796(3) 0.15431(13) 0.0196(4) Uani 1 1 d . . . . .
H30 H 0.078601 0.645293 0.192064 0.023 Uiso 1 1 calc R U . . .
C31 C 0.07909(17) 0.5861(3) 0.06956(13) 0.0201(4) Uani 1 1 d . . . . .
H31 H 0.014017 0.656929 0.050203 0.024 Uiso 1 1 calc R U . . .
C4 C 0.67551(17) 0.4336(3) 0.46857(12) 0.0174(4) Uani 1 1 d . . . . .
H4 H 0.702237 0.380948 0.521338 0.021 Uiso 1 1 calc R U . . .
C5 C 0.57259(16) 0.5270(3) 0.45747(12) 0.0170(4) Uani 1 1 d . . . . .
C34 C 0.27015(17) 0.3849(3) 0.12774(13) 0.0206(4) Uani 1 1 d . . . . .
H34 H 0.336100 0.316331 0.147272 0.025 Uiso 1 1 calc R U . . .
C6 C 0.53290(17) 0.5979(3) 0.37816(13) 0.0183(4) Uani 1 1 d . . . . .
H6 H 0.461706 0.657844 0.369039 0.022 Uiso 1 1 calc R U . . .
C2 C 0.70041(17) 0.4925(3) 0.32540(12) 0.0178(4) Uani 1 1 d . . . . .
C23 C 0.01788(18) 0.5842(4) 0.53042(13) 0.0225(5) Uani 1 1 d . . . . .
H23 H -0.053582 0.643499 0.523033 0.027 Uiso 1 1 calc R U . . .
C15 C 0.72713(17) 0.3859(4) 1.03869(13) 0.0233(5) Uani 1 1 d . . . . .
H15A H 0.730987 0.260875 1.017093 0.035 Uiso 1 1 calc R U . . .
H15B H 0.736159 0.382754 1.099853 0.035 Uiso 1 1 calc R U . . .
H15C H 0.787610 0.460017 1.020423 0.035 Uiso 1 1 calc R U . . .
C28 C 0.25782(17) 0.4596(3) 0.27353(13) 0.0212(4) Uani 1 1 d . . . . .
H28 H 0.326851 0.395637 0.288635 0.025 Uiso 1 1 calc R U . . .
C27 C 0.16111(17) 0.4108(3) 0.61602(13) 0.0211(5) Uani 1 1 d . . . . .
H27 H 0.187872 0.352226 0.667425 0.025 Uiso 1 1 calc R U . . .
C33 C 0.23228(17) 0.3896(3) 0.04274(13) 0.0210(4) Uani 1 1 d . . . . .
H33 H 0.272660 0.324935 0.005270 0.025 Uiso 1 1 calc R U . . .
C16 C 0.55948(18) 0.5679(4) 1.06533(13) 0.0228(5) Uani 1 1 d . . . . .
H16A H 0.566617 0.699612 1.055366 0.034 Uiso 1 1 calc R U . . .
H16B H 0.592735 0.538956 1.122668 0.034 Uiso 1 1 calc R U . . .
H16C H 0.479426 0.533638 1.057210 0.034 Uiso 1 1 calc R U . . .
C22 C 0.05590(17) 0.4966(4) 0.60531(13) 0.0203(5) Uani 1 1 d . . . . .
C1 C 0.86774(18) 0.4078(4) 0.26889(14) 0.0300(6) Uani 1 1 d . . . . .
H1A H 0.902236 0.420390 0.217572 0.045 Uiso 1 1 calc R U . . .
H1B H 0.861554 0.277610 0.282451 0.045 Uiso 1 1 calc R U . . .
H1C H 0.914869 0.470152 0.314835 0.045 Uiso 1 1 calc R U . . .
C36 C 0.1588(2) 0.3961(4) -0.13119(14) 0.0291(5) Uani 1 1 d . . . . .
H36A H 0.236521 0.442253 -0.125515 0.044 Uiso 1 1 calc R U . . .
H36B H 0.121971 0.416495 -0.188430 0.044 Uiso 1 1 calc R U . . .
H36C H 0.159794 0.264518 -0.118779 0.044 Uiso 1 1 calc R U . . .
C35 C -0.0036(2) 0.5936(4) -0.10472(14) 0.0301(5) Uani 1 1 d . . . . .
H35A H -0.068776 0.541201 -0.082387 0.045 Uiso 1 1 calc R U . . .
H35B H -0.015832 0.586067 -0.165829 0.045 Uiso 1 1 calc R U . . .
H35C H 0.005573 0.722224 -0.087624 0.045 Uiso 1 1 calc R U . . .
C21 C -0.11331(19) 0.5653(5) 0.66253(15) 0.0399(7) Uani 1 1 d . . . . .
H21A H -0.159527 0.513541 0.613277 0.060 Uiso 1 1 calc R U . . .
H21B H -0.106028 0.697926 0.655358 0.060 Uiso 1 1 calc R U . . .
H21C H -0.149473 0.540770 0.712262 0.060 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 C2 1.381(2) . ?
O1 C1 1.425(3) . ?
O21 C22 1.383(3) . ?
O21 C21 1.421(3) . ?
N2 N1 1.376(2) . ?
N2 C8 1.287(3) . ?
N22 N21 1.379(2) . ?
N22 C28 1.287(3) . ?
N1 H1 0.90(3) . ?
N1 C5 1.400(3) . ?
N3 C12 1.376(2) . ?
N3 C15 1.453(3) . ?
N3 C16 1.454(3) . ?
N23 C32 1.376(3) . ?
N23 C36 1.460(3) . ?
N23 C35 1.440(3) . ?
N21 H21 0.92(3) . ?
N21 C25 1.412(3) . ?
C7 H7 0.9500 . ?
C7 C6 1.382(3) . ?
C7 C2 1.393(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.417(3) . ?
C11 C10 1.378(3) . ?
C9 C8 1.462(3) . ?
C9 C10 1.403(3) . ?
C9 C14 1.397(3) . ?
C12 C13 1.406(3) . ?
C29 C30 1.402(3) . ?
C29 C34 1.398(3) . ?
C29 C28 1.453(3) . ?
C8 H8 0.9500 . ?
C24 H24 0.9500 . ?
C24 C25 1.388(3) . ?
C24 C23 1.392(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.402(3) . ?
C3 C2 1.388(3) . ?
C10 H10 0.9500 . ?
C13 H13 0.9500 . ?
C13 C14 1.388(3) . ?
C25 C26 1.395(3) . ?
C32 C31 1.416(3) . ?
C32 C33 1.405(3) . ?
C14 H14 0.9500 . ?
C26 H26 0.9500 . ?
C26 C27 1.386(3) . ?
C30 H30 0.9500 . ?
C30 C31 1.386(3) . ?
C31 H31 0.9500 . ?
C4 H4 0.9500 . ?
C4 C5 1.396(3) . ?
C5 C6 1.403(3) . ?
C34 H34 0.9500 . ?
C34 C33 1.387(3) . ?
C6 H6 0.9500 . ?
C23 H23 0.9500 . ?
C23 C22 1.389(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C28 H28 0.9500 . ?
C27 H27 0.9500 . ?
C27 C22 1.394(3) . ?
C33 H33 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

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
C2 O1 C1 116.88(16) . . ?
C22 O21 C21 116.87(18) . . ?
C8 N2 N1 114.91(17) . . ?
C28 N22 N21 115.72(19) . . ?
N2 N1 H1 116.6(17) . . ?
N2 N1 C5 119.09(17) . . ?
C5 N1 H1 119.4(17) . . ?
C12 N3 C15 119.99(16) . . ?
C12 N3 C16 119.79(17) . . ?
C15 N3 C16 117.84(16) . . ?
C32 N23 C36 119.97(18) . . ?
C32 N23 C35 120.77(18) . . ?
C35 N23 C36 119.25(17) . . ?
N22 N21 H21 117.9(17) . . ?
N22 N21 C25 116.91(17) . . ?
C25 N21 H21 109.1(17) . . ?
C6 C7 H7 119.8 . . ?
C6 C7 C2 120.32(18) . . ?
C2 C7 H7 119.8 . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C10 C11 C12 121.18(19) . . ?
C10 C9 C8 123.48(18) . . ?
C14 C9 C8 119.23(19) . . ?
C14 C9 C10 117.29(18) . . ?
N3 C12 C11 121.41(18) . . ?
N3 C12 C13 121.35(18) . . ?
C13 C12 C11 117.23(18) . . ?
C30 C29 C28 124.61(19) . . ?
C34 C29 C30 117.42(19) . . ?
C34 C29 C28 117.96(19) . . ?
N2 C8 C9 122.12(19) . . ?
N2 C8 H8 118.9 . . ?
C9 C8 H8 118.9 . . ?
C25 C24 H24 119.8 . . ?
C25 C24 C23 120.5(2) . . ?
C23 C24 H24 119.8 . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C2 C3 C4 119.65(19) . . ?
C11 C10 C9 121.54(19) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C12 C13 H13 119.6 . . ?
C14 C13 C12 120.77(18) . . ?
C14 C13 H13 119.6 . . ?
C24 C25 N21 122.1(2) . . ?
C24 C25 C26 119.20(19) . . ?
C26 C25 N21 118.66(19) . . ?
N23 C32 C31 121.60(19) . . ?
N23 C32 C33 120.94(19) . . ?
C33 C32 C31 117.45(18) . . ?
C9 C14 H14 119.0 . . ?
C13 C14 C9 121.92(19) . . ?
C13 C14 H14 119.0 . . ?
C25 C26 H26 119.7 . . ?
C27 C26 C25 120.55(19) . . ?
C27 C26 H26 119.7 . . ?
C29 C30 H30 119.3 . . ?
C31 C30 C29 121.4(2) . . ?
C31 C30 H30 119.3 . . ?
C32 C31 H31 119.5 . . ?
C30 C31 C32 121.0(2) . . ?
C30 C31 H31 119.5 . . ?
C3 C4 H4 119.6 . . ?
C5 C4 C3 120.73(18) . . ?
C5 C4 H4 119.6 . . ?
N1 C5 C6 118.48(18) . . ?
C4 C5 N1 122.92(18) . . ?
C4 C5 C6 118.58(19) . . ?
C29 C34 H34 119.0 . . ?
C33 C34 C29 121.93(19) . . ?
C33 C34 H34 119.0 . . ?
C7 C6 C5 120.71(19) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
O1 C2 C7 115.55(18) . . ?
O1 C2 C3 124.50(19) . . ?
C3 C2 C7 119.95(18) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 C24 120.0(2) . . ?
C22 C23 H23 120.0 . . ?
N3 C15 H15A 109.5 . . ?
N3 C15 H15B 109.5 . . ?
N3 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N22 C28 C29 122.67(19) . . ?
N22 C28 H28 118.7 . . ?
C29 C28 H28 118.7 . . ?
C26 C27 H27 120.0 . . ?
C26 C27 C22 120.0(2) . . ?
C22 C27 H27 120.0 . . ?
C32 C33 H33 119.6 . . ?
C34 C33 C32 120.79(19) . . ?
C34 C33 H33 119.6 . . ?
N3 C16 H16A 109.5 . . ?
N3 C16 H16B 109.5 . . ?
N3 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O21 C22 C23 124.8(2) . . ?
O21 C22 C27 115.43(19) . . ?
C23 C22 C27 119.8(2) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N23 C36 H36A 109.5 . . ?
N23 C36 H36B 109.5 . . ?
N23 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
N23 C35 H35A 109.5 . . ?
N23 C35 H35B 109.5 . . ?
N23 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
O21 C21 H21A 109.5 . . ?
O21 C21 H21B 109.5 . . ?
O21 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
N2 N1 C5 C4 15.5(3) . . . . ?
N2 N1 C5 C6 -165.8(2) . . . . ?
N22 N21 C25 C24 -21.9(3) . . . . ?
N22 N21 C25 C26 159.4(2) . . . . ?
N1 N2 C8 C9 175.24(19) . . . . ?
N1 C5 C6 C7 178.9(2) . . . . ?
N3 C12 C13 C14 178.8(2) . . . . ?
N23 C32 C31 C30 179.3(2) . . . . ?
N23 C32 C33 C34 -179.5(2) . . . . ?
N21 N22 C28 C29 179.4(2) . . . . ?
N21 C25 C26 C27 179.4(2) . . . . ?
C11 C12 C13 C14 -1.9(3) . . . . ?
C12 C11 C10 C9 -0.2(3) . . . . ?
C12 C13 C14 C9 -0.1(3) . . . . ?
C29 C30 C31 C32 0.5(3) . . . . ?
C29 C34 C33 C32 -0.2(3) . . . . ?
C8 N2 N1 C5 167.7(2) . . . . ?
C8 C9 C10 C11 178.7(2) . . . . ?
C8 C9 C14 C13 -178.5(2) . . . . ?
C24 C25 C26 C27 0.7(3) . . . . ?
C24 C23 C22 O21 -178.3(2) . . . . ?
C24 C23 C22 C27 0.4(4) . . . . ?
C3 C4 C5 N1 -179.0(2) . . . . ?
C3 C4 C5 C6 2.3(3) . . . . ?
C10 C11 C12 N3 -178.7(2) . . . . ?
C10 C11 C12 C13 2.1(3) . . . . ?
C10 C9 C8 N2 -4.1(3) . . . . ?
C10 C9 C14 C13 2.0(3) . . . . ?
C25 C24 C23 C22 0.6(4) . . . . ?
C25 C26 C27 C22 0.3(4) . . . . ?
C14 C9 C8 N2 176.4(2) . . . . ?
C14 C9 C10 C11 -1.9(3) . . . . ?
C26 C27 C22 O21 177.9(2) . . . . ?
C26 C27 C22 C23 -0.9(4) . . . . ?
C30 C29 C34 C33 -0.8(3) . . . . ?
C30 C29 C28 N22 4.8(4) . . . . ?
C31 C32 C33 C34 1.3(3) . . . . ?
C4 C3 C2 O1 178.2(2) . . . . ?
C4 C3 C2 C7 -1.3(3) . . . . ?
C4 C5 C6 C7 -2.3(3) . . . . ?
C34 C29 C30 C31 0.6(3) . . . . ?
C34 C29 C28 N22 -173.8(2) . . . . ?
C6 C7 C2 O1 -178.2(2) . . . . ?
C6 C7 C2 C3 1.3(3) . . . . ?
C2 C7 C6 C5 0.5(3) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
C23 C24 C25 N21 -179.9(2) . . . . ?
C23 C24 C25 C26 -1.2(3) . . . . ?
C15 N3 C12 C11 10.5(3) . . . . ?
C15 N3 C12 C13 -170.4(2) . . . . ?
C28 N22 N21 C25 -155.0(2) . . . . ?
C28 C29 C30 C31 -177.9(2) . . . . ?
C28 C29 C34 C33 177.8(2) . . . . ?
C33 C32 C31 C30 -1.5(3) . . . . ?
C16 N3 C12 C11 172.6(2) . . . . ?
C16 N3 C12 C13 -8.3(3) . . . . ?
C1 O1 C2 C7 176.5(2) . . . . ?
C1 O1 C2 C3 -3.1(3) . . . . ?
C36 N23 C32 C31 177.8(2) . . . . ?
C36 N23 C32 C33 -1.4(3) . . . . ?
C35 N23 C32 C31 -1.3(3) . . . . ?
C35 N23 C32 C33 179.6(2) . . . . ?
C21 O21 C22 C23 0.3(4) . . . . ?
C21 O21 C22 C27 -178.4(2) . . . . ?

_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 1.304
_oxdiff_exptl_absorpt_empirical_full_min 0.590
