# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_ps20_zolte2_twin1_hklf4
_database_code_depnum_ccdc_archive 'CCDC 2285246'
loop_
_audit_author_name
_audit_author_address
'Paulina Sobczak'
;Lodz University of Technology
Poland
;
_audit_update_record             
;
2023-07-28 deposited with the CCDC.	2023-10-25 downloaded from the CCDC.
;
_audit_creation_date             2023-01-05
_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 H14 N O3, N O3'
_chemical_formula_sum            'C15 H14 N2 O6'
_chemical_formula_weight         318.28
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C15 H14 N2 O6 '
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/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                   4.83768(17)
_cell_length_b                   14.8178(5)
_cell_length_c                   20.0275(6)
_cell_angle_alpha                90
_cell_angle_beta                 95.964(3)
_cell_angle_gamma                90
_cell_volume                     1427.87(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7177
_cell_measurement_temperature    99.9(8)
_cell_measurement_theta_max      78.1810
_cell_measurement_theta_min      3.6500
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.876
_exptl_absorpt_coefficient_mu    0.988
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.922
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.79a (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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_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 10 1 0.0175
-3 2 -1 0.0718
0 2 -13 0.0095
0 -2 13 0.0105
3 -1 0 0.0599
0 -10 1 0.0247
0 8 8 0.0141
0 -7 -9 0.0187

_exptl_crystal_size_max          0.137
_exptl_crystal_size_mid          0.044
_exptl_crystal_size_min          0.021
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
0.3541 9.5460 0.5607 0.2151 0.8957 -0.3891
-3.0370 1.7474 -0.9852 0.1016 0.4330 0.8957
0.1155 1.9723 -12.6906 -0.8994 0.4278 0.0904
-0.1424 -1.9979 12.6902 0.9000 -0.4281 -0.0815
3.0951 -1.3694 -0.1764 -0.1821 -0.3783 -0.9076
-0.3725 -9.5438 0.7287 -0.1193 -0.9188 0.3762
0.0450 7.7601 7.6316 0.7137 0.6097 -0.3448
-0.2525 -6.5250 -9.3435 -0.8055 -0.4392 0.3978

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0791
_diffrn_reflns_av_unetI/netI     0.0131
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.923
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            3740
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.923
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.444
_diffrn_reflns_theta_min         3.718
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(8)
_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 0.923
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -20.00  27.00   0.50   20.00    --  -48.87  19.00-180.00   94
  2  ω    -20.00  27.00   0.50   20.00    --  -48.87  19.00-150.00   94
  3  ω    -20.00  27.00   0.50   20.00    --  -48.87  19.00  60.00   94
  4  ω    -20.00  27.00   0.50   20.00    --  -48.87  19.00 150.00   94
  5  ω    -27.00  20.00   0.50   20.00    --   48.87 -19.00   0.00   94
  6  ω    -27.00  20.00   0.50   20.00    --   48.87 -19.00 -90.00   94
  7  ω    -41.00 -13.00   0.50   80.00    --  -88.50  38.00 -30.00   56
  8  ω    -84.00 -20.00   0.50   80.00    --  -88.50 113.00  31.00  128
  9  ω    -66.00 -17.00   0.50   80.00    --  -88.50  57.00 120.00   98
 10  ω    -87.00 -19.00   0.50   80.00    --  -88.50 125.00  60.00  136
 11  ω    -66.00 -17.00   0.50   80.00    --  -88.50  57.00  30.00   98
 12  ω    -87.00 -19.00   0.50   80.00    --  -88.50 125.00  90.00  136
 13  ω    -41.00 -13.00   0.50   80.00    --  -88.50  38.00-120.00   56
 14  ω    -41.00 -13.00   0.50   80.00    --  -88.50  38.00   0.00   56
 15  ω    -66.00 -17.00   0.50   80.00    --  -88.50  57.00  60.00   98
 16  ω     41.00 106.00   0.50   80.00    --  110.00 -99.00  90.00  130
 17  ω     38.00  66.00   0.50   80.00    --  110.00 -57.00-120.00   56
 18  ω     94.00 178.00   0.50   80.00    --  110.00  57.00  60.00  168
 19  ω     38.00  66.00   0.50   80.00    --  110.00 -57.00 150.00   56
 20  ω     94.00 178.00   0.50   80.00    --  110.00 125.00 120.00  168
 21  ω     38.00  66.00   0.50   80.00    --  110.00 -57.00  30.00   56
 22  ω     94.00 178.00   0.50   80.00    --  110.00  57.00 -60.00  168
 23  ω     25.00 114.00   0.50   20.00    --   48.87  77.00-120.00  178
 24  ω     25.00  88.00   0.50   20.00    --   48.87  77.00 150.00  126
 25  ω     25.00 114.00   0.50   20.00    --   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      -0.0458447000
_diffrn_orient_matrix_UB_12      0.0199091000
_diffrn_orient_matrix_UB_13      0.0735447000
_diffrn_orient_matrix_UB_21      -0.0799950000
_diffrn_orient_matrix_UB_22      0.0979285000
_diffrn_orient_matrix_UB_23      -0.0192161000
_diffrn_orient_matrix_UB_31      -0.3066855000
_diffrn_orient_matrix_UB_32      -0.0285445000
_diffrn_orient_matrix_UB_33      -0.0143537000
_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                3222
_reflns_number_total             3740
_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 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.79a (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         0.385
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3740
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0568
_refine_ls_restrained_S_all      1.092
_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)+(0.1081P)²+0.7391P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1666
_refine_ls_wR_factor_ref         0.1731
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.764(2)
 0.236(2)
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, All O(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 N1(H1A), C6(H6), C14(H14), C13(H13), C3(H3), C4(H4), C7(H7), C8(H8), C10(H10),
  C11(H11)
3.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
3.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O4 O 0.6713(4) 0.55957(13) 0.36290(10) 0.0348(5) Uani 1 1 d . . . . .
O2 O -0.3451(3) 0.54531(13) 0.07150(10) 0.0312(4) Uani 1 1 d . . . . .
O1 O -0.2398(4) 0.41876(15) 0.01804(10) 0.0340(5) Uani 1 1 d . . . . .
H1 H -0.387715 0.431425 -0.005872 0.051 Uiso 1 1 calc R U . . .
O3 O 1.6981(4) 0.28245(15) 0.48249(10) 0.0362(5) Uani 1 1 d . . . . .
O5 O 0.6238(4) 0.70445(14) 0.35744(13) 0.0434(5) Uani 1 1 d . . . . .
O6 O 0.8160(5) 0.63450(16) 0.28017(11) 0.0462(6) Uani 1 1 d . . . . .
N2 N 0.7045(4) 0.63379(15) 0.33382(12) 0.0293(5) Uani 1 1 d . . . . .
N1 N 0.6662(4) 0.41101(15) 0.27415(11) 0.0255(5) Uani 1 1 d . . . . .
H1A H 0.704149 0.457170 0.301208 0.031 Uiso 1 1 calc R U . . .
C6 C 0.2773(5) 0.49718(18) 0.22557(13) 0.0271(5) Uani 1 1 d . . . . .
H6 H 0.305233 0.536688 0.263020 0.032 Uiso 1 1 calc R U . . .
C9 C 1.0385(5) 0.32956(19) 0.33817(13) 0.0270(5) Uani 1 1 d . . . . .
C1 C -0.2022(5) 0.47495(17) 0.06659(12) 0.0241(5) Uani 1 1 d . . . . .
C14 C 1.1481(5) 0.40159(19) 0.37810(13) 0.0278(5) Uani 1 1 d . . . . .
H14 H 1.069769 0.460103 0.371474 0.033 Uiso 1 1 calc R U . . .
C5 C 0.4494(5) 0.42280(18) 0.22096(13) 0.0253(5) Uani 1 1 d . . . . .
C13 C 1.3683(5) 0.3886(2) 0.42692(13) 0.0298(6) Uani 1 1 d . . . . .
H13 H 1.441443 0.437896 0.453453 0.036 Uiso 1 1 calc R U . . .
C3 C 0.1974(5) 0.38046(18) 0.11586(13) 0.0270(5) Uani 1 1 d . . . . .
H3 H 0.167983 0.340768 0.078549 0.032 Uiso 1 1 calc R U . . .
C4 C 0.4124(5) 0.36366(18) 0.16639(14) 0.0276(5) Uani 1 1 d . . . . .
H4 H 0.531316 0.313044 0.163730 0.033 Uiso 1 1 calc R U . . .
C7 C 0.0655(5) 0.51318(18) 0.17527(13) 0.0260(5) Uani 1 1 d . . . . .
H7 H -0.053698 0.563662 0.178145 0.031 Uiso 1 1 calc R U . . .
C8 C 0.8130(5) 0.33814(19) 0.28629(13) 0.0275(5) Uani 1 1 d . . . . .
H8 H 0.767323 0.286974 0.258758 0.033 Uiso 1 1 calc R U . . .
C10 C 1.1594(6) 0.24358(19) 0.34881(15) 0.0337(6) Uani 1 1 d . . . . .
H10 H 1.089952 0.194219 0.321803 0.040 Uiso 1 1 calc R U . . .
C2 C 0.0265(5) 0.45501(17) 0.12004(13) 0.0248(5) Uani 1 1 d . . . . .
C12 C 1.4828(5) 0.30236(19) 0.43701(13) 0.0291(6) Uani 1 1 d . . . . .
C15 C 1.8120(6) 0.3521(2) 0.52698(15) 0.0373(7) Uani 1 1 d . . . . .
H15A H 1.857970 0.404769 0.500712 0.056 Uiso 1 1 calc R U . . .
H15B H 1.980670 0.329710 0.553108 0.056 Uiso 1 1 calc R U . . .
H15C H 1.675245 0.369243 0.557503 0.056 Uiso 1 1 calc R U . . .
C11 C 1.3760(6) 0.2302(2) 0.39765(15) 0.0362(6) Uani 1 1 d . . . . .
H11 H 1.453614 0.171665 0.404698 0.043 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
O4 N2 1.263(3) . ?
O2 C1 1.260(3) . ?
O1 H1 0.8400 . ?
O1 C1 1.279(3) . ?
O3 C12 1.343(3) . ?
O3 C15 1.435(4) . ?
O5 N2 1.229(3) . ?
O6 N2 1.251(3) . ?
N1 H1A 0.8800 . ?
N1 C5 1.426(3) . ?
N1 C8 1.301(3) . ?
C6 H6 0.9500 . ?
C6 C5 1.390(4) . ?
C6 C7 1.381(4) . ?
C9 C14 1.404(4) . ?
C9 C8 1.432(4) . ?
C9 C10 1.409(4) . ?
C1 C2 1.487(3) . ?
C14 H14 0.9500 . ?
C14 C13 1.383(4) . ?
C5 C4 1.398(4) . ?
C13 H13 0.9500 . ?
C13 C12 1.399(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.396(4) . ?
C3 C2 1.387(4) . ?
C4 H4 0.9500 . ?
C7 H7 0.9500 . ?
C7 C2 1.399(4) . ?
C8 H8 0.9500 . ?
C10 H10 0.9500 . ?
C10 C11 1.372(4) . ?
C12 C11 1.395(4) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C11 H11 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
C1 O1 H1 109.5 . . ?
C12 O3 C15 118.9(2) . . ?
O5 N2 O4 120.2(2) . . ?
O5 N2 O6 120.4(2) . . ?
O6 N2 O4 119.4(2) . . ?
C5 N1 H1A 117.1 . . ?
C8 N1 H1A 117.1 . . ?
C8 N1 C5 125.9(2) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
C7 C6 C5 119.5(2) . . ?
C14 C9 C8 124.0(2) . . ?
C14 C9 C10 118.4(2) . . ?
C10 C9 C8 117.6(2) . . ?
O2 C1 O1 124.2(2) . . ?
O2 C1 C2 118.8(2) . . ?
O1 C1 C2 117.0(2) . . ?
C9 C14 H14 119.5 . . ?
C13 C14 C9 121.0(3) . . ?
C13 C14 H14 119.5 . . ?
C6 C5 N1 116.5(2) . . ?
C6 C5 C4 121.4(2) . . ?
C4 C5 N1 122.1(2) . . ?
C14 C13 H13 120.2 . . ?
C14 C13 C12 119.6(3) . . ?
C12 C13 H13 120.2 . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.1(2) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 C5 118.7(2) . . ?
C3 C4 H4 120.7 . . ?
C6 C7 H7 120.0 . . ?
C6 C7 C2 120.0(2) . . ?
C2 C7 H7 120.0 . . ?
N1 C8 C9 124.7(2) . . ?
N1 C8 H8 117.7 . . ?
C9 C8 H8 117.7 . . ?
C9 C10 H10 119.6 . . ?
C11 C10 C9 120.8(3) . . ?
C11 C10 H10 119.6 . . ?
C3 C2 C1 121.2(2) . . ?
C3 C2 C7 120.4(2) . . ?
C7 C2 C1 118.4(2) . . ?
O3 C12 C13 124.5(2) . . ?
O3 C12 C11 115.5(2) . . ?
C11 C12 C13 120.0(2) . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C10 C11 C12 120.2(3) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?

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
O2 C1 C2 C3 -177.4(2) . . . . ?
O2 C1 C2 C7 2.9(3) . . . . ?
O1 C1 C2 C3 2.3(3) . . . . ?
O1 C1 C2 C7 -177.4(2) . . . . ?
O3 C12 C11 C10 -178.8(3) . . . . ?
N1 C5 C4 C3 -179.2(2) . . . . ?
C6 C5 C4 C3 0.0(4) . . . . ?
C6 C7 C2 C1 -179.4(2) . . . . ?
C6 C7 C2 C3 0.8(4) . . . . ?
C9 C14 C13 C12 -0.4(4) . . . . ?
C9 C10 C11 C12 -1.0(5) . . . . ?
C14 C9 C8 N1 -6.8(4) . . . . ?
C14 C9 C10 C11 1.0(4) . . . . ?
C14 C13 C12 O3 179.3(2) . . . . ?
C14 C13 C12 C11 0.4(4) . . . . ?
C5 N1 C8 C9 176.9(2) . . . . ?
C5 C6 C7 C2 -0.4(4) . . . . ?
C13 C12 C11 C10 0.2(4) . . . . ?
C4 C3 C2 C1 179.4(2) . . . . ?
C4 C3 C2 C7 -0.9(4) . . . . ?
C7 C6 C5 N1 179.2(2) . . . . ?
C7 C6 C5 C4 0.0(4) . . . . ?
C8 N1 C5 C6 165.8(2) . . . . ?
C8 N1 C5 C4 -15.1(4) . . . . ?
C8 C9 C14 C13 -179.3(2) . . . . ?
C8 C9 C10 C11 -179.9(3) . . . . ?
C10 C9 C14 C13 -0.3(4) . . . . ?
C10 C9 C8 N1 174.1(3) . . . . ?
C2 C3 C4 C5 0.5(4) . . . . ?
C15 O3 C12 C13 3.8(4) . . . . ?
C15 O3 C12 C11 -177.3(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.934
_oxdiff_exptl_absorpt_empirical_full_min 0.695
_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 0.764(2) 6603 7686 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000
0.0000 1.0000
2 0.236(2) 0 7686 nmt -0.9997 0.0004 -0.0000 0.0013 -1.0005 0.0008 0.8578
-0.0006 0.9997

_twin_special_details            
;
Component 2 rotated by 179.9930° 
around [-0.00 0.00 1.00] (reciprocal) or [0.39 -0.00 0.92] (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_ps010-5
_database_code_depnum_ccdc_archive 'CCDC 2285248'
loop_
_audit_author_name
_audit_author_address
'Paulina Sobczak'
;Lodz University of Technology
Poland
;
_audit_update_record             
;
2023-07-28 deposited with the CCDC.	2023-10-25 downloaded from the CCDC.
;
_audit_creation_date             2022-12-06
_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 H14 N O3, Br, H2 O'
_chemical_formula_sum            'C15 H16 Br N O4'
_chemical_formula_weight         354.20
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C15 H16 Br1 N1 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'
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      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                   4.72040(10)
_cell_length_b                   21.1550(5)
_cell_length_c                   15.1364(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.616(2)
_cell_angle_gamma                90
_cell_volume                     1509.95(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    14065
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      78.7200
_cell_measurement_theta_min      3.5850
_shelx_estimated_absorpt_T_max   0.880
_shelx_estimated_absorpt_T_min   0.332
_exptl_absorpt_coefficient_mu    3.854
_exptl_absorpt_correction_T_max  0.912
_exptl_absorpt_correction_T_min  0.466
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.558
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             720
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 10 6 0.0172
0 -10 -6 0.0172
3 3 -1 0.1634
-3 -1 2 0.1764
-3 0 5 0.1544
0 -13 -4 0.0143
0 -12 -5 0.0130
0 8 8 0.0197
0 0 -10 0.0241
0 13 3 0.0193
0 -2 10 0.0196
0 10 -6 0.0295
0 11 -6 0.0247

_exptl_crystal_size_max          0.367
_exptl_crystal_size_mid          0.054
_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
0.0613 10.4787 6.3319 -0.7412 -0.4019 -0.5377
-0.0613 -10.4787 -6.3319 0.7412 0.4019 0.5377
2.9930 2.8698 -0.8681 -0.5780 -0.3166 0.7521
-3.0186 -1.3227 1.8332 0.4730 0.2596 -0.8420
-2.7104 0.1297 4.9765 0.3188 -0.0439 -0.9468
-0.1832 -12.5658 -3.8890 0.8831 0.1656 0.4391
-0.3630 -12.0187 -4.5500 0.8737 0.2607 0.4108
0.0402 7.8064 8.0677 -0.5696 -0.5995 -0.5622
0.1333 0.1927 -9.8241 0.0230 0.8657 0.5000
0.4385 13.0831 2.5670 -0.9438 -0.0759 -0.3218
-0.1167 -1.6392 9.7546 0.0717 -0.8862 -0.4577
0.4254 10.4160 -6.3127 -0.7160 0.6787 0.1634
0.2239 10.8935 -5.9668 -0.7234 0.6854 0.0829

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0516
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            22483
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.882
_diffrn_reflns_theta_min         4.180
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(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 0.968
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -61.00  26.00   0.50    4.55    --  -49.71  19.00   0.00  174
  2  ω     27.00 115.00   0.50    4.55    --   49.71  77.00 -60.00  176
  3  ω     98.00 178.00   0.50   16.07    --  107.75  38.00  30.00  160
  4  ω     85.00 173.00   0.50   16.07    --  107.75  77.00-180.00  176
  5  ω     39.00 110.00   0.50   16.07    --  107.75 -99.00  30.00  142
  6  ω     33.00  71.00   0.50   16.07    --  107.75 -38.00 -60.00   76
  7  ω     33.00  71.00   0.50   16.07    --  107.75 -38.00 -90.00   76
  8  ω     39.00 110.00   0.50   16.07    --  107.75 -99.00 -30.00  142
  9  ω     33.00  71.00   0.50   16.07    --  107.75 -38.00-180.00   76
 10  ω     38.00 117.00   0.50   16.07    --  107.75-125.00 -60.00  158
 11  ω     33.00  71.00   0.50   16.07    --  107.75 -38.00  60.00   76
 12  ω     33.00  71.00   0.50   16.07    --  107.75 -38.00  30.00   76
 13  ω     37.00  96.00   0.50   16.07    --  107.75 -57.00 120.00  118
 14  ω     39.00 110.00   0.50   16.07    --  107.75 -99.00 150.00  142
 15  ω     37.00  96.00   0.50   16.07    --  107.75 -57.00 150.00  118
 16  ω     35.00 121.00   0.50    4.55    --   49.71  57.00 150.00  172
 17  ω     59.00 120.00   0.50    4.55    --   49.71 178.00 150.00  122
 18  ω     27.00 115.00   0.50    4.55    --   49.71  77.00  30.00  176
 19  ω     27.00 115.00   0.50    4.55    --   49.71  77.00-150.00  176
 20  ω     35.00 121.00   0.50    4.55    --   49.71  57.00-150.00  172
 21  ω     27.00 115.00   0.50    4.55    --   49.71  77.00-120.00  176
 22  ω     27.00 115.00   0.50    4.55    --   49.71  77.00  60.00  176
 23  ω    -92.00 -16.00   0.50   16.07    --  -86.25 125.00  60.00  152
 24  ω    -97.00 -11.00   0.50   16.07    --  -86.25  19.00-120.00  172
 25  ω   -124.00 -39.00   0.50    4.55    --  -49.71 -38.00  30.00  170
 26  ω   -120.00 -38.00   0.50    4.55    --  -49.71-178.00  30.00  164
 27  ω   -155.00 -82.00   0.50   16.07    --  -86.25 -99.00 150.00  146
 28  ω   -151.00 -64.00   0.50   16.07    --  -86.25 -77.00  90.00  174
 29  ω   -151.00 -64.00   0.50   16.07    --  -86.25 -77.00  30.00  174
 30  ω   -157.00 -85.50   0.50   16.07    --  -86.25 -57.00-150.00  143
;
_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      -0.1307539000
_diffrn_orient_matrix_UB_12      -0.0666901000
_diffrn_orient_matrix_UB_13      -0.0054233000
_diffrn_orient_matrix_UB_21      -0.1478950000
_diffrn_orient_matrix_UB_22      0.0167720000
_diffrn_orient_matrix_UB_23      -0.0898027000
_diffrn_orient_matrix_UB_31      0.2603704000
_diffrn_orient_matrix_UB_32      -0.0239355000
_diffrn_orient_matrix_UB_33      -0.0478263000
_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                2808
_reflns_number_total             3130
_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         1.271
_refine_diff_density_min         -0.489
_refine_diff_density_rms         0.094
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3130
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0441
_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)+(0.0443P)²+4.7773P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1075
_refine_ls_wR_factor_ref         0.1102
_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, All O(H,H) groups
2.a Riding coordinates:
 O4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1A), C7(H7), C6(H6), C14(H14), C11(H11), C8(H8), C4(H4), C13(H13), C3(H3),
  C10(H10)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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 -0.83882(7) 0.29734(2) 0.35945(2) 0.02400(13) Uani 1 1 d . . . . .
O3 O 1.7208(5) 0.94858(11) 0.46216(16) 0.0247(5) Uani 1 1 d . . . . .
O2 O -0.2211(6) 0.54315(13) 0.24441(18) 0.0341(6) Uani 1 1 d . . . . .
O1 O -0.0919(6) 0.51307(13) 0.38217(19) 0.0378(6) Uani 1 1 d . . . . .
H1 H -0.210663 0.484063 0.372298 0.057 Uiso 1 1 calc R U . . .
N1 N 0.7563(6) 0.74427(13) 0.34699(18) 0.0209(6) Uani 1 1 d . . . . .
H1A H 0.783351 0.765694 0.298258 0.025 Uiso 1 1 calc R U . . .
O4 O -0.3445(7) 0.40515(15) 0.3646(2) 0.0473(8) Uani 1 1 d . . . . .
H4A H -0.519789 0.378924 0.367554 0.071 Uiso 1 1 d R U . . .
H4B H -0.160889 0.375514 0.365554 0.071 Uiso 1 1 d R U . . .
C1 C -0.0792(7) 0.54962(15) 0.3106(2) 0.0208(6) Uani 1 1 d . . . . .
C12 C 1.5236(6) 0.90305(15) 0.4447(2) 0.0198(6) Uani 1 1 d . . . . .
C7 C 0.1865(7) 0.64099(16) 0.2540(2) 0.0216(6) Uani 1 1 d . . . . .
H7 H 0.081540 0.636059 0.199344 0.026 Uiso 1 1 calc R U . . .
C6 C 0.3895(7) 0.68824(16) 0.2628(2) 0.0212(6) Uani 1 1 d . . . . .
H6 H 0.422946 0.715743 0.214769 0.025 Uiso 1 1 calc R U . . .
C9 C 1.1193(7) 0.80845(15) 0.4218(2) 0.0213(7) Uani 1 1 d . . . . .
C14 C 1.1759(7) 0.84930(16) 0.3519(2) 0.0237(7) Uani 1 1 d . . . . .
H14 H 1.075640 0.844383 0.296430 0.028 Uiso 1 1 calc R U . . .
C5 C 0.5435(7) 0.69490(15) 0.3428(2) 0.0204(6) Uani 1 1 d . . . . .
C11 C 1.4737(7) 0.86173(17) 0.5141(2) 0.0243(7) Uani 1 1 d . . . . .
H11 H 1.578164 0.865918 0.568945 0.029 Uiso 1 1 calc R U . . .
C2 C 0.1350(7) 0.60088(16) 0.3238(2) 0.0216(7) Uani 1 1 d . . . . .
C8 C 0.9093(7) 0.75924(16) 0.4167(2) 0.0215(6) Uani 1 1 d . . . . .
H8 H 0.880623 0.735782 0.469090 0.026 Uiso 1 1 calc R U . . .
C4 C 0.4941(7) 0.65608(17) 0.4136(2) 0.0251(7) Uani 1 1 d . . . . .
H4 H 0.598892 0.661416 0.468176 0.030 Uiso 1 1 calc R U . . .
C13 C 1.3757(7) 0.89661(16) 0.3628(2) 0.0215(6) Uani 1 1 d . . . . .
H13 H 1.412474 0.924429 0.315364 0.026 Uiso 1 1 calc R U . . .
C3 C 0.2889(7) 0.60898(18) 0.4043(2) 0.0267(7) Uani 1 1 d . . . . .
H3 H 0.253029 0.582156 0.452871 0.032 Uiso 1 1 calc R U . . .
C10 C 1.2738(7) 0.81513(16) 0.5031(2) 0.0233(7) Uani 1 1 d . . . . .
H10 H 1.239224 0.787159 0.550490 0.028 Uiso 1 1 calc R U . . .
C15 C 1.7735(7) 0.99255(16) 0.3938(2) 0.0243(7) Uani 1 1 d . . . . .
H15A H 1.841391 0.969944 0.342369 0.037 Uiso 1 1 calc R U . . .
H15B H 1.917570 1.022982 0.415009 0.037 Uiso 1 1 calc R U . . .
H15C H 1.597709 1.015028 0.376913 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
O3 C12 1.357(4) . ?
O3 C15 1.422(4) . ?
O2 C1 1.188(4) . ?
O1 H1 0.8400 . ?
O1 C1 1.334(4) . ?
N1 H1A 0.8800 . ?
N1 C5 1.448(4) . ?
N1 C8 1.291(4) . ?
O4 H4A 0.9988 . ?
O4 H4B 1.0694 . ?
C1 C2 1.490(4) . ?
C12 C11 1.395(5) . ?
C12 C13 1.402(4) . ?
C7 H7 0.9500 . ?
C7 C6 1.387(5) . ?
C7 C2 1.386(5) . ?
C6 H6 0.9500 . ?
C6 C5 1.391(4) . ?
C9 C14 1.401(5) . ?
C9 C8 1.437(5) . ?
C9 C10 1.409(5) . ?
C14 H14 0.9500 . ?
C14 C13 1.380(5) . ?
C5 C4 1.378(5) . ?
C11 H11 0.9500 . ?
C11 C10 1.369(5) . ?
C2 C3 1.400(5) . ?
C8 H8 0.9500 . ?
C4 H4 0.9500 . ?
C4 C3 1.392(5) . ?
C13 H13 0.9500 . ?
C3 H3 0.9500 . ?
C10 H10 0.9500 . ?
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
C12 O3 C15 117.6(2) . . ?
C1 O1 H1 109.5 . . ?
C5 N1 H1A 117.5 . . ?
C8 N1 H1A 117.5 . . ?
C8 N1 C5 125.0(3) . . ?
H4A O4 H4B 110.3 . . ?
O2 C1 O1 125.0(3) . . ?
O2 C1 C2 123.4(3) . . ?
O1 C1 C2 111.6(3) . . ?
O3 C12 C11 115.8(3) . . ?
O3 C12 C13 123.4(3) . . ?
C11 C12 C13 120.7(3) . . ?
C6 C7 H7 119.6 . . ?
C2 C7 H7 119.6 . . ?
C2 C7 C6 120.8(3) . . ?
C7 C6 H6 120.4 . . ?
C7 C6 C5 119.2(3) . . ?
C5 C6 H6 120.4 . . ?
C14 C9 C8 124.2(3) . . ?
C14 C9 C10 119.3(3) . . ?
C10 C9 C8 116.6(3) . . ?
C9 C14 H14 119.7 . . ?
C13 C14 C9 120.7(3) . . ?
C13 C14 H14 119.7 . . ?
C6 C5 N1 116.4(3) . . ?
C4 C5 N1 122.5(3) . . ?
C4 C5 C6 121.1(3) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 C12 119.9(3) . . ?
C10 C11 H11 120.1 . . ?
C7 C2 C1 119.0(3) . . ?
C7 C2 C3 119.1(3) . . ?
C3 C2 C1 121.8(3) . . ?
N1 C8 C9 125.4(3) . . ?
N1 C8 H8 117.3 . . ?
C9 C8 H8 117.3 . . ?
C5 C4 H4 120.3 . . ?
C5 C4 C3 119.3(3) . . ?
C3 C4 H4 120.3 . . ?
C12 C13 H13 120.5 . . ?
C14 C13 C12 119.1(3) . . ?
C14 C13 H13 120.5 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.4(3) . . ?
C4 C3 H3 119.8 . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.3(3) . . ?
C11 C10 H10 119.8 . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 C12 C11 C10 178.6(3) . . . . ?
O3 C12 C13 C14 -179.0(3) . . . . ?
O2 C1 C2 C7 -4.3(5) . . . . ?
O2 C1 C2 C3 176.8(3) . . . . ?
O1 C1 C2 C7 176.4(3) . . . . ?
O1 C1 C2 C3 -2.5(5) . . . . ?
N1 C5 C4 C3 -179.0(3) . . . . ?
C1 C2 C3 C4 177.9(3) . . . . ?
C12 C11 C10 C9 0.4(5) . . . . ?
C7 C6 C5 N1 178.7(3) . . . . ?
C7 C6 C5 C4 -1.1(5) . . . . ?
C7 C2 C3 C4 -1.0(5) . . . . ?
C6 C7 C2 C1 -178.3(3) . . . . ?
C6 C7 C2 C3 0.7(5) . . . . ?
C6 C5 C4 C3 0.8(5) . . . . ?
C9 C14 C13 C12 0.5(5) . . . . ?
C14 C9 C8 N1 3.5(5) . . . . ?
C14 C9 C10 C11 1.1(5) . . . . ?
C5 N1 C8 C9 -179.5(3) . . . . ?
C5 C4 C3 C2 0.3(5) . . . . ?
C11 C12 C13 C14 1.0(5) . . . . ?
C2 C7 C6 C5 0.4(5) . . . . ?
C8 N1 C5 C6 176.5(3) . . . . ?
C8 N1 C5 C4 -3.6(5) . . . . ?
C8 C9 C14 C13 178.1(3) . . . . ?
C8 C9 C10 C11 -178.6(3) . . . . ?
C13 C12 C11 C10 -1.4(5) . . . . ?
C10 C9 C14 C13 -1.5(5) . . . . ?
C10 C9 C8 N1 -176.8(3) . . . . ?
C15 O3 C12 C11 -178.6(3) . . . . ?
C15 O3 C12 C13 1.4(5) . . . . ?

_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 1.993
_oxdiff_exptl_absorpt_empirical_full_min 0.432
####################################################################### 
# 
# 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_ps10_s04_2_twin1_hklf4
_database_code_depnum_ccdc_archive 'CCDC 2285247'
loop_
_audit_author_name
_audit_author_address
'Paulina Sobczak'
;Lodz University of Technology
Poland
;
_audit_update_record             
;
2023-07-28 deposited with the CCDC.	2023-10-25 downloaded from the CCDC.
;
_audit_creation_date             2023-07-28
_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 H14 N O3, H O4 S'
_chemical_formula_sum            'C15 H15 N O7 S'
_chemical_formula_weight         353.34
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C15 H15 N1 O7 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           7
_space_group_name_H-M_alt        'P 1 c 1'
_space_group_name_Hall           'P -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'

_cell_length_a                   4.47140(10)
_cell_length_b                   9.3275(2)
_cell_length_c                   17.7797(5)
_cell_angle_alpha                90
_cell_angle_beta                 90.109(2)
_cell_angle_gamma                90
_cell_volume                     741.54(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    12883
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      78.7550
_cell_measurement_theta_min      4.7330
_shelx_estimated_absorpt_T_max   0.946
_shelx_estimated_absorpt_T_min   0.617
_exptl_absorpt_coefficient_mu    2.327
_exptl_absorpt_correction_T_max  0.955
_exptl_absorpt_correction_T_min  0.729
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.86a (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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.582
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             368
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -6 -3 0.0229
0 -5 7 0.0182
0 5 -7 0.0182
0 -6 -3 0.0173
-3 -1 -2 0.1055
2 4 3 0.0915
-3 1 -1 0.1105
3 -2 0 0.1062
0 1 -11 0.0133
0 5 8 0.0178
0 5 -8 0.0171
0 -5 6 0.0121
0 5 -6 0.0121

_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.054
_exptl_crystal_size_min          0.024
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
-0.0193 -5.8476 -2.9828 0.0193 0.0715 -0.9973
-0.4631 -4.8763 6.5924 0.7536 -0.1816 -0.6317
0.4631 4.8763 -6.5924 -0.7536 0.1816 0.6317
0.2163 -5.8489 -2.8493 0.0382 0.1507 -0.9878
-2.7712 -1.3453 -2.2614 -0.2178 -0.9139 -0.3426
2.0948 3.8476 3.1480 0.1545 0.6531 0.7414
-2.8344 1.1875 -1.0102 -0.2319 -0.9689 0.0864
2.6981 -2.2209 0.4074 0.2246 0.9368 -0.2681
0.3886 1.1931 -11.2131 -0.9707 0.2320 -0.0622
0.0383 4.5566 7.5955 0.4225 -0.0991 0.9009
-0.0447 4.5736 -7.5605 -0.8368 0.0200 0.5471
-0.0146 -5.2598 5.7154 0.7133 -0.0166 -0.7006
0.0146 5.2598 -5.7154 -0.7133 0.0166 0.7006

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_unetI/netI     0.0161
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            24898
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.925
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.665
_diffrn_reflns_theta_min         4.741
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 300K'
_diffrn_measured_fraction_theta_full 0.987
_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    6.00    --  -48.87 -57.00 -30.00  174
  2  ω   -120.00 -41.00   0.50    6.00    --  -48.87-178.00-180.00  158
  3  ω    -41.00  27.00   0.50    6.00    --  -48.87  38.00 120.00  136
  4  ω    -20.00  27.00   0.50    6.00    --  -48.87  19.00-150.00   94
  5  ω     25.00 114.00   0.50    6.00    --   48.87  77.00  30.00  178
  6  ω    -27.00  20.00   0.50    6.00    --   48.87 -19.00   0.00   94
  7  ω    -41.00 -13.00   0.50   16.00    --  -88.50  38.00-180.00   56
  8  ω    -41.00 -13.00   0.50   16.00    --  -88.50  38.00 150.00   56
  9  ω    -87.00 -19.00   0.50   16.00    --  -88.50 125.00  90.00  136
 10  ω   -164.00 -75.00   0.50   16.00    --  -88.50 -38.00-150.00  178
 11  ω    -41.00 -13.00   0.50   16.00    --  -88.50  38.00  90.00   56
 12  ω    -87.00 -19.00   0.50   16.00    --  -88.50 125.00-150.00  136
 13  ω   -160.00 -16.00   0.50   16.00    --  -88.50   0.00-150.00  288
 14  ω   -157.00 -85.00   0.50   16.00    --  -88.50 -99.00-150.00  144
 15  ω    -41.00 -13.00   0.50   16.00    --  -88.50  38.00 120.00   56
 16  ω    -41.00 -13.00   0.50   16.00    --  -88.50  38.00 -60.00   56
 17  ω    -87.00 -19.00   0.50   16.00    --  -88.50 125.00 150.00  136
 18  ω     86.00 176.00   0.50   16.00    --  110.00  77.00  30.00  180
 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  60.00  144
 21  ω     41.00 106.00   0.50   16.00    --  110.00 -99.00   0.00  130
 22  ω     41.00 106.00   0.50   16.00    --  110.00 -99.00-120.00  130
 23  ω     94.00 178.00   0.50   16.00    --  110.00 125.00  60.00  168
 24  ω     45.00 134.00   0.50   16.00    --  110.00 -77.00  60.00  178
 25  ω     41.00 106.00   0.50   16.00    --  110.00 -99.00  90.00  130
 26  ω     41.00 106.00   0.50   16.00    --  110.00 -99.00-180.00  130
 27  ω     38.00  66.00   0.50   16.00    --  110.00 -57.00 -90.00   56
 28  ω     25.00 114.00   0.50    6.00    --   48.87  77.00-120.00  178
 29  ω     25.00 114.00   0.50    6.00    --   48.87  77.00   0.00  178
 30  ω     25.00 114.00   0.50    6.00    --   48.87  77.00 120.00  178
 31  ω     25.00 114.00   0.50    6.00    --   48.87  77.00 -90.00  178
 32  ω     33.00 121.00   0.50    6.00    --   48.87  57.00  90.00  176
 33  ω     25.00 114.00   0.50    6.00    --   48.87  77.00 150.00  178
 34  ω   -154.00 -65.00   0.50   16.00    --  -88.50 -77.00  30.00  178
 35  ω   -154.00 -65.00   0.50   16.00    --  -88.50 -77.00-180.00  178
 36  ω   -154.00 -65.00   0.50   16.00    --  -88.50 -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      0.0331452000
_diffrn_orient_matrix_UB_12      -0.0456742000
_diffrn_orient_matrix_UB_13      0.0828592000
_diffrn_orient_matrix_UB_21      0.3417892000
_diffrn_orient_matrix_UB_22      -0.0083829000
_diffrn_orient_matrix_UB_23      -0.0097371000
_diffrn_orient_matrix_UB_31      0.0276038000
_diffrn_orient_matrix_UB_32      0.1585269000
_diffrn_orient_matrix_UB_33      0.0233726000
_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         0.890
_reflns_Friedel_fraction_full    0.972
_reflns_Friedel_fraction_max     0.874
_reflns_number_gt                2972
_reflns_number_total             2993
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.86a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.86a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.86a (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         0.226
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.393(18)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         2993
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0265
_refine_ls_R_factor_gt           0.0260
_refine_ls_restrained_S_all      1.073
_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)+(0.0432P)²+0.2527P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0708
_refine_ls_wR_factor_ref         0.0711
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.607(18)
 0.393(18)
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, All O(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C10(H10), C13(H13), C8(H8), C14(H14), C11(H11), C3(H3), C7(H7),
 C6(H6), C4(H4)
3.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
3.c Idealised tetrahedral OH refined as rotating group:
 O2(H2), O7(H7A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S -0.46296(12) 0.76836(5) 0.86509(4) 0.01577(14) Uani 1 1 d . . . . .
O3 O 1.5875(4) 0.63539(19) 0.12259(10) 0.0209(4) Uani 1 1 d . . . . .
O6 O -0.2378(4) 0.88077(18) 0.87850(11) 0.0213(4) Uani 1 1 d . . . . .
O5 O -0.3413(4) 0.62918(18) 0.88352(11) 0.0228(4) Uani 1 1 d . . . . .
O2 O -0.2446(4) 0.70658(19) 0.67340(11) 0.0223(4) Uani 1 1 d . . . . .
H2 H -0.347554 0.736770 0.709546 0.033 Uiso 1 1 calc R U . . .
O1 O -0.1797(4) 0.9409(2) 0.65246(11) 0.0269(4) Uani 1 1 d . . . . .
O4 O -0.5945(4) 0.7781(2) 0.79058(11) 0.0246(4) Uani 1 1 d . . . . .
O7 O -0.7149(4) 0.7982(2) 0.92296(11) 0.0242(4) Uani 1 1 d . . . . .
H7A H -0.871630 0.822341 0.900115 0.036 Uiso 1 1 calc R U . . .
N1 N 0.6466(4) 0.6712(2) 0.39522(11) 0.0155(4) Uani 1 1 d . . . . .
H1 H 0.667088 0.579292 0.385241 0.019 Uiso 1 1 calc R U . . .
C9 C 1.0118(5) 0.7244(3) 0.29819(14) 0.0150(5) Uani 1 1 d . . . . .
C10 C 1.1525(5) 0.8394(3) 0.26045(14) 0.0166(5) Uani 1 1 d . . . . .
H10 H 1.110216 0.935086 0.275275 0.020 Uiso 1 1 calc R U . . .
C13 C 1.2773(5) 0.5579(3) 0.21922(15) 0.0184(5) Uani 1 1 d . . . . .
H13 H 1.325190 0.462290 0.205341 0.022 Uiso 1 1 calc R U . . .
C8 C 0.8046(5) 0.7618(3) 0.35545(14) 0.0157(5) Uani 1 1 d . . . . .
H8 H 0.778415 0.860930 0.365746 0.019 Uiso 1 1 calc R U . . .
C5 C 0.4440(5) 0.7105(3) 0.45351(13) 0.0147(4) Uani 1 1 d . . . . .
C14 C 1.0811(5) 0.5822(3) 0.27679(14) 0.0171(5) Uani 1 1 d . . . . .
H14 H 0.991526 0.503719 0.302308 0.021 Uiso 1 1 calc R U . . .
C12 C 1.4096(5) 0.6736(3) 0.18022(14) 0.0165(5) Uani 1 1 d . . . . .
C2 C 0.0609(5) 0.7748(3) 0.57137(14) 0.0158(5) Uani 1 1 d . . . . .
C11 C 1.3511(5) 0.8147(3) 0.20221(14) 0.0177(5) Uani 1 1 d . . . . .
H11 H 1.446299 0.892623 0.177529 0.021 Uiso 1 1 calc R U . . .
C3 C 0.1975(5) 0.8843(3) 0.53051(14) 0.0191(5) Uani 1 1 d . . . . .
H3 H 0.158542 0.981432 0.543178 0.023 Uiso 1 1 calc R U . . .
C7 C 0.1114(5) 0.6319(3) 0.55157(14) 0.0168(5) Uani 1 1 d . . . . .
H7 H 0.014721 0.556991 0.578386 0.020 Uiso 1 1 calc R U . . .
C6 C 0.3034(5) 0.5995(3) 0.49253(14) 0.0168(5) Uani 1 1 d . . . . .
H6 H 0.338716 0.502503 0.478842 0.020 Uiso 1 1 calc R U . . .
C15 C 1.7147(6) 0.7473(3) 0.07697(16) 0.0224(5) Uani 1 1 d . . . . .
H15A H 1.835896 0.704459 0.036969 0.034 Uiso 1 1 calc R U . . .
H15B H 1.841014 0.809005 0.108328 0.034 Uiso 1 1 calc R U . . .
H15C H 1.553741 0.804461 0.054558 0.034 Uiso 1 1 calc R U . . .
C1 C -0.1331(5) 0.8166(3) 0.63590(14) 0.0174(5) Uani 1 1 d . . . . .
C4 C 0.3889(5) 0.8530(3) 0.47177(15) 0.0186(5) Uani 1 1 d . . . . .
H4 H 0.481652 0.928040 0.444215 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
S1 O6 1.4729(18) . ?
S1 O5 1.4451(19) . ?
S1 O4 1.451(2) . ?
S1 O7 1.5524(18) . ?
O3 C12 1.347(3) . ?
O3 C15 1.439(3) . ?
O2 H2 0.8400 . ?
O2 C1 1.322(3) . ?
O1 C1 1.214(3) . ?
O7 H7A 0.8400 . ?
N1 H1 0.8800 . ?
N1 C8 1.310(3) . ?
N1 C5 1.426(3) . ?
C9 C10 1.413(3) . ?
C9 C8 1.421(3) . ?
C9 C14 1.415(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.384(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.368(4) . ?
C13 C12 1.413(4) . ?
C8 H8 0.9500 . ?
C5 C6 1.396(3) . ?
C5 C4 1.391(3) . ?
C14 H14 0.9500 . ?
C12 C11 1.398(4) . ?
C2 C3 1.395(3) . ?
C2 C7 1.397(3) . ?
C2 C1 1.491(3) . ?
C11 H11 0.9500 . ?
C3 H3 0.9500 . ?
C3 C4 1.382(4) . ?
C7 H7 0.9500 . ?
C7 C6 1.391(3) . ?
C6 H6 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C4 H4 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
O6 S1 O7 105.17(11) . . ?
O5 S1 O6 110.23(12) . . ?
O5 S1 O4 114.53(11) . . ?
O5 S1 O7 106.52(12) . . ?
O4 S1 O6 112.27(11) . . ?
O4 S1 O7 107.48(11) . . ?
C12 O3 C15 118.2(2) . . ?
C1 O2 H2 109.5 . . ?
S1 O7 H7A 109.5 . . ?
C8 N1 H1 117.6 . . ?
C8 N1 C5 124.8(2) . . ?
C5 N1 H1 117.6 . . ?
C10 C9 C8 116.5(2) . . ?
C10 C9 C14 119.1(2) . . ?
C14 C9 C8 124.5(2) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 C9 121.1(2) . . ?
C11 C10 H10 119.5 . . ?
C14 C13 H13 119.7 . . ?
C14 C13 C12 120.7(2) . . ?
C12 C13 H13 119.7 . . ?
N1 C8 C9 125.6(2) . . ?
N1 C8 H8 117.2 . . ?
C9 C8 H8 117.2 . . ?
C6 C5 N1 117.3(2) . . ?
C4 C5 N1 121.9(2) . . ?
C4 C5 C6 120.8(2) . . ?
C9 C14 H14 120.1 . . ?
C13 C14 C9 119.8(2) . . ?
C13 C14 H14 120.1 . . ?
O3 C12 C13 114.8(2) . . ?
O3 C12 C11 124.9(2) . . ?
C11 C12 C13 120.2(2) . . ?
C3 C2 C7 119.7(2) . . ?
C3 C2 C1 117.7(2) . . ?
C7 C2 C1 122.5(2) . . ?
C10 C11 C12 119.1(2) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 H11 120.5 . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.8(2) . . ?
C4 C3 H3 119.6 . . ?
C2 C7 H7 120.1 . . ?
C6 C7 C2 119.8(2) . . ?
C6 C7 H7 120.1 . . ?
C5 C6 H6 120.2 . . ?
C7 C6 C5 119.6(2) . . ?
C7 C6 H6 120.2 . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O2 C1 C2 113.9(2) . . ?
O1 C1 O2 123.6(2) . . ?
O1 C1 C2 122.4(2) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 C5 119.2(2) . . ?
C3 C4 H4 120.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 C12 C11 C10 177.1(2) . . . . ?
N1 C5 C6 C7 177.9(2) . . . . ?
N1 C5 C4 C3 -177.9(2) . . . . ?
C9 C10 C11 C12 0.7(4) . . . . ?
C10 C9 C8 N1 178.1(2) . . . . ?
C10 C9 C14 C13 -1.3(4) . . . . ?
C13 C12 C11 C10 -2.7(3) . . . . ?
C8 N1 C5 C6 -177.2(2) . . . . ?
C8 N1 C5 C4 2.2(3) . . . . ?
C8 C9 C10 C11 -178.0(2) . . . . ?
C8 C9 C14 C13 177.9(2) . . . . ?
C5 N1 C8 C9 178.7(2) . . . . ?
C14 C9 C10 C11 1.3(4) . . . . ?
C14 C9 C8 N1 -1.1(4) . . . . ?
C14 C13 C12 O3 -177.0(2) . . . . ?
C14 C13 C12 C11 2.8(3) . . . . ?
C12 C13 C14 C9 -0.7(4) . . . . ?
C2 C3 C4 C5 0.2(4) . . . . ?
C2 C7 C6 C5 0.0(4) . . . . ?
C3 C2 C7 C6 1.7(4) . . . . ?
C3 C2 C1 O2 -177.5(2) . . . . ?
C3 C2 C1 O1 1.7(4) . . . . ?
C7 C2 C3 C4 -1.7(4) . . . . ?
C7 C2 C1 O2 1.8(3) . . . . ?
C7 C2 C1 O1 -179.1(2) . . . . ?
C6 C5 C4 C3 1.5(4) . . . . ?
C15 O3 C12 C13 176.0(2) . . . . ?
C15 O3 C12 C11 -3.9(4) . . . . ?
C1 C2 C3 C4 177.6(2) . . . . ?
C1 C2 C7 C6 -177.6(2) . . . . ?
C4 C5 C6 C7 -1.5(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 1.877
_oxdiff_exptl_absorpt_empirical_full_min 0.526
_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 0.607(18) 11416 2874 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000
0.0000 1.0000
2 0.393(18) 11501 2874 nmt 1.0000 -0.0001 0.0000 0.0025 0.5687 0.4314 -0.0031
-1.5676 0.5686

_twin_special_details            
;
Component 2 rotated by 55.3443° 
around [-1.00 0.00 0.01] (reciprocal) or [-1.00 0.00 -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_ps10_1
_database_code_depnum_ccdc_archive 'CCDC 2285251'
loop_
_audit_author_name
_audit_author_address
'Paulina Sobczak'
;Lodz University of Technology
Poland
;
_audit_update_record             
;
2023-07-28 deposited with the CCDC.	2023-10-25 downloaded from the CCDC.
;
_audit_creation_date             2022-12-08
_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 H14 N O3, Cl, H2 O'
_chemical_formula_sum            'C15 H16 Cl N O4'
_chemical_formula_weight         309.74
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C15 H16 Cl1 N1 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'
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                   4.70370(10)
_cell_length_b                   20.9656(3)
_cell_length_c                   14.8427(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.1960(10)
_cell_angle_gamma                90
_cell_volume                     1462.65(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7863
_cell_measurement_temperature    100.00(13)
_cell_measurement_theta_max      78.5710
_cell_measurement_theta_min      3.6380
_shelx_estimated_absorpt_T_max   0.952
_shelx_estimated_absorpt_T_min   0.602
_exptl_absorpt_coefficient_mu    2.458
_exptl_absorpt_correction_T_max  0.962
_exptl_absorpt_correction_T_min  0.781
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_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
-3 -2 0 0.1211
3 -1 1 0.1020
0 12 -5 0.0130
0 8 8 0.0064
0 8 -8 0.0055
0 -10 -6 0.0137
0 -14 0 0.0155
0 -7 8 0.0111

_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.03
_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
-3.0225 -1.7366 -0.2541 0.0889 0.1811 0.9794
2.9952 -0.9379 1.3946 0.0092 0.0254 -0.9996
-0.2263 11.5327 -5.0315 -0.4204 -0.8849 0.2007
0.1352 7.9968 7.7621 -0.9322 0.3294 -0.1503
0.0257 7.7865 -7.8975 -0.0244 -0.9876 0.1554
0.0534 -10.2142 -6.3658 0.9900 -0.1291 0.0572
0.0530 -13.6021 0.1989 0.8217 0.5658 -0.0680
0.0149 -6.5947 8.4188 -0.0779 0.9818 -0.1734

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.936
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14629
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.411
_diffrn_reflns_theta_min         3.650
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(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 0.936
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -25.00  43.00   0.50    1.50    --   49.96 -38.00 150.00  136
  2  ω     36.00 117.00   0.50    4.00    --  107.75-125.00  30.00  162
  3  ω     43.00 105.00   0.50    4.00    --  107.75 -77.00 -60.00  124
  4  ω     43.00 105.00   0.50    4.00    --  107.75 -77.00-150.00  124
  5  ω     97.00 178.00   0.50    4.00    --  107.75  19.00  30.00  162
  6  ω     93.00 178.00   0.50    4.00    --  107.75  57.00 -30.00  170
  7  ω     39.00 110.00   0.50    4.00    --  107.75 -99.00  60.00  142
  8  ω     35.00 121.00   0.50    1.50    --   49.96  57.00  90.00  172
  9  ω     28.00 114.00   0.50    1.50    --   49.96  77.00   0.00  172
 10  ω    -25.00  26.00   0.50    1.50    --   49.96 -19.00 -90.00  102
 11  ω    -26.00  25.00   0.50    1.50    --  -50.71  19.00-180.00  102
 12  ω    -43.00 -11.00   0.50    4.00    --  -86.25  38.00 -30.00   64
 13  ω    -66.00 -15.00   0.50    4.00    --  -86.25  57.00  90.00  102
 14  ω    -92.00 -15.00   0.50    4.00    --  -86.25 125.00  30.00  154
 15  ω    -92.00 -15.00   0.50    4.00    --  -86.25 125.00  90.00  154
 16  ω   -126.00 -40.00   0.50    1.50    --  -50.71 -19.00-120.00  172
 17  ω   -122.00 -36.00   0.50    1.50    --  -50.71 -57.00-180.00  172
 18  ω   -161.00-120.00   0.50    4.00    --  -86.25 -19.00-150.00   82
 19  ω   -157.00 -71.00   0.50    4.00    --  -86.25 -57.00 120.00  172
;
_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      0.0105595000
_diffrn_orient_matrix_UB_12      -0.0612057000
_diffrn_orient_matrix_UB_13      -0.0572196000
_diffrn_orient_matrix_UB_21      -0.0437591000
_diffrn_orient_matrix_UB_22      -0.0405274000
_diffrn_orient_matrix_UB_23      0.0849466000
_diffrn_orient_matrix_UB_31      -0.3246003000
_diffrn_orient_matrix_UB_32      0.0034836000
_diffrn_orient_matrix_UB_33      -0.0172954000
_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                2579
_reflns_number_total             2923
_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         0.794
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2923
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0392
_refine_ls_restrained_S_all      1.044
_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)+(0.0459P)²+1.4067P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0992
_refine_ls_wR_factor_ref         0.1029
_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, All O(H,H) groups
2.a Riding coordinates:
 O4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1A), C6(H6), C7(H7), C13(H13), C14(H14), C8(H8), C11(H11), C10(H10),
 C4(H4), C3(H3)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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
Cl1 Cl 1.81971(9) 0.70728(2) 0.65066(3) 0.01811(13) Uani 1 1 d . . . . .
O3 O -0.7171(3) 0.05449(6) 0.53409(8) 0.0184(3) Uani 1 1 d . . . . .
O2 O 1.2307(3) 0.46262(7) 0.75444(9) 0.0248(3) Uani 1 1 d . . . . .
O1 O 1.0945(3) 0.49562(7) 0.61621(10) 0.0300(4) Uani 1 1 d . . . . .
H1 H 1.201888 0.526591 0.629003 0.045 Uiso 1 1 calc R U . . .
N1 N 0.2536(3) 0.26002(7) 0.64747(10) 0.0164(3) Uani 1 1 d . . . . .
H1A H 0.223816 0.238768 0.697362 0.020 Uiso 1 1 calc R U . . .
O4 O 1.3234(3) 0.60744(7) 0.63941(10) 0.0296(3) Uani 1 1 d . . . . .
H4A H 1.479258 0.629855 0.642578 0.044 Uiso 1 1 d R U . . .
H4B H 1.187798 0.635594 0.636398 0.044 Uiso 1 1 d R U . . .
C12 C -0.5182(4) 0.09984(8) 0.55088(12) 0.0152(4) Uani 1 1 d . . . . .
C9 C -0.1097(4) 0.19536(8) 0.57138(12) 0.0168(4) Uani 1 1 d . . . . .
C5 C 0.4660(4) 0.30944(8) 0.65186(12) 0.0155(4) Uani 1 1 d . . . . .
C2 C 0.8743(4) 0.40452(8) 0.67239(12) 0.0156(4) Uani 1 1 d . . . . .
C6 C 0.6203(4) 0.31548(9) 0.73336(12) 0.0162(4) Uani 1 1 d . . . . .
H6 H 0.585808 0.287342 0.781904 0.019 Uiso 1 1 calc R U . . .
C7 C 0.8242(4) 0.36285(8) 0.74306(12) 0.0158(4) Uani 1 1 d . . . . .
H7 H 0.930906 0.366954 0.798416 0.019 Uiso 1 1 calc R U . . .
C1 C 1.0866(4) 0.45640(8) 0.68687(12) 0.0171(4) Uani 1 1 d . . . . .
C13 C -0.3730(4) 0.10748(8) 0.63429(12) 0.0167(4) Uani 1 1 d . . . . .
H13 H -0.412716 0.080299 0.683450 0.020 Uiso 1 1 calc R U . . .
C14 C -0.1716(4) 0.15498(9) 0.64413(12) 0.0188(4) Uani 1 1 d . . . . .
H14 H -0.073114 0.160613 0.700649 0.023 Uiso 1 1 calc R U . . .
C15 C -0.7735(4) 0.01067(9) 0.60532(12) 0.0186(4) Uani 1 1 d . . . . .
H15A H -0.922862 -0.019198 0.585006 0.028 Uiso 1 1 calc R U . . .
H15B H -0.836453 0.034313 0.657911 0.028 Uiso 1 1 calc R U . . .
H15C H -0.599704 -0.013081 0.621763 0.028 Uiso 1 1 calc R U . . .
C8 C 0.1023(4) 0.24421(8) 0.57589(12) 0.0164(4) Uani 1 1 d . . . . .
H8 H 0.135341 0.267035 0.522000 0.020 Uiso 1 1 calc R U . . .
C11 C -0.4643(4) 0.14058(9) 0.47844(12) 0.0185(4) Uani 1 1 d . . . . .
H11 H -0.567821 0.135809 0.422628 0.022 Uiso 1 1 calc R U . . .
C10 C -0.2614(4) 0.18732(9) 0.48860(12) 0.0180(4) Uani 1 1 d . . . . .
H10 H -0.222995 0.214499 0.439309 0.022 Uiso 1 1 calc R U . . .
C4 C 0.5165(4) 0.34961(9) 0.58006(12) 0.0200(4) Uani 1 1 d . . . . .
H4 H 0.412965 0.344609 0.524298 0.024 Uiso 1 1 calc R U . . .
C3 C 0.7201(4) 0.39722(9) 0.59054(12) 0.0205(4) Uani 1 1 d . . . . .
H3 H 0.754958 0.425098 0.541727 0.025 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 C12 1.350(2) . ?
O3 C15 1.433(2) . ?
O2 C1 1.196(2) . ?
O1 H1 0.8400 . ?
O1 C1 1.334(2) . ?
N1 H1A 0.8800 . ?
N1 C5 1.439(2) . ?
N1 C8 1.299(2) . ?
O4 H4A 0.8703 . ?
O4 H4B 0.8690 . ?
C12 C13 1.400(2) . ?
C12 C11 1.404(3) . ?
C9 C14 1.411(3) . ?
C9 C8 1.429(3) . ?
C9 C10 1.407(3) . ?
C5 C6 1.392(2) . ?
C5 C4 1.386(3) . ?
C2 C7 1.392(3) . ?
C2 C1 1.487(2) . ?
C2 C3 1.399(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.385(3) . ?
C7 H7 0.9500 . ?
C13 H13 0.9500 . ?
C13 C14 1.378(3) . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C8 H8 0.9500 . ?
C11 H11 0.9500 . ?
C11 C10 1.372(3) . ?
C10 H10 0.9500 . ?
C4 H4 0.9500 . ?
C4 C3 1.388(3) . ?
C3 H3 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
C12 O3 C15 117.50(13) . . ?
C1 O1 H1 109.5 . . ?
C5 N1 H1A 117.3 . . ?
C8 N1 H1A 117.3 . . ?
C8 N1 C5 125.34(16) . . ?
H4A O4 H4B 104.6 . . ?
O3 C12 C13 123.70(16) . . ?
O3 C12 C11 115.55(15) . . ?
C13 C12 C11 120.75(16) . . ?
C14 C9 C8 123.92(17) . . ?
C10 C9 C14 118.94(16) . . ?
C10 C9 C8 117.14(16) . . ?
C6 C5 N1 116.27(16) . . ?
C4 C5 N1 122.81(16) . . ?
C4 C5 C6 120.92(17) . . ?
C7 C2 C1 118.84(16) . . ?
C7 C2 C3 119.24(17) . . ?
C3 C2 C1 121.91(17) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 C5 119.45(17) . . ?
C7 C6 H6 120.3 . . ?
C2 C7 H7 119.7 . . ?
C6 C7 C2 120.55(16) . . ?
C6 C7 H7 119.7 . . ?
O2 C1 O1 124.06(17) . . ?
O2 C1 C2 123.84(17) . . ?
O1 C1 C2 112.09(15) . . ?
C12 C13 H13 120.5 . . ?
C14 C13 C12 119.10(17) . . ?
C14 C13 H13 120.5 . . ?
C9 C14 H14 119.6 . . ?
C13 C14 C9 120.89(17) . . ?
C13 C14 H14 119.6 . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 C8 C9 125.49(17) . . ?
N1 C8 H8 117.3 . . ?
C9 C8 H8 117.3 . . ?
C12 C11 H11 120.1 . . ?
C10 C11 C12 119.71(17) . . ?
C10 C11 H11 120.1 . . ?
C9 C10 H10 119.7 . . ?
C11 C10 C9 120.57(17) . . ?
C11 C10 H10 119.7 . . ?
C5 C4 H4 120.4 . . ?
C5 C4 C3 119.26(16) . . ?
C3 C4 H4 120.4 . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.56(17) . . ?
C4 C3 H3 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 C12 C13 C14 179.41(16) . . . . ?
O3 C12 C11 C10 -178.70(16) . . . . ?
N1 C5 C6 C7 -178.71(16) . . . . ?
N1 C5 C4 C3 178.27(17) . . . . ?
C12 C13 C14 C9 -0.4(3) . . . . ?
C12 C11 C10 C9 -0.9(3) . . . . ?
C5 N1 C8 C9 -179.70(16) . . . . ?
C5 C6 C7 C2 0.4(3) . . . . ?
C5 C4 C3 C2 0.4(3) . . . . ?
C6 C5 C4 C3 -1.3(3) . . . . ?
C7 C2 C1 O2 4.4(3) . . . . ?
C7 C2 C1 O1 -174.69(16) . . . . ?
C7 C2 C3 C4 0.9(3) . . . . ?
C1 C2 C7 C6 177.47(16) . . . . ?
C1 C2 C3 C4 -177.85(17) . . . . ?
C13 C12 C11 C10 1.8(3) . . . . ?
C14 C9 C8 N1 -3.8(3) . . . . ?
C14 C9 C10 C11 -0.6(3) . . . . ?
C15 O3 C12 C13 -2.3(2) . . . . ?
C15 O3 C12 C11 178.29(15) . . . . ?
C8 N1 C5 C6 -175.10(17) . . . . ?
C8 N1 C5 C4 5.3(3) . . . . ?
C8 C9 C14 C13 -177.97(17) . . . . ?
C8 C9 C10 C11 178.68(17) . . . . ?
C11 C12 C13 C14 -1.2(3) . . . . ?
C10 C9 C14 C13 1.3(3) . . . . ?
C10 C9 C8 N1 176.96(17) . . . . ?
C4 C5 C6 C7 0.8(3) . . . . ?
C3 C2 C7 C6 -1.3(3) . . . . ?
C3 C2 C1 O2 -176.84(18) . . . . ?
C3 C2 C1 O1 4.0(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 1.280
_oxdiff_exptl_absorpt_empirical_full_min 0.556
####################################################################### 
# 
# 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_ps010-po4
_database_code_depnum_ccdc_archive 'CCDC 2285250'
loop_
_audit_author_name
_audit_author_address
'Paulina Sobczak'
;Lodz University of Technology
Poland
;
_audit_update_record             
;
2023-07-28 deposited with the CCDC.	2023-10-25 downloaded from the CCDC.
;
_audit_creation_date             2022-12-08
_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 H14 N O3, H2 O4 P'
_chemical_formula_sum            'C15 H16 N O7 P'
_chemical_formula_weight         353.26
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C15 H16 N1 O7 P1 '
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'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.99120(10)
_cell_length_b                   21.7863(2)
_cell_length_c                   9.04030(10)
_cell_angle_alpha                90
_cell_angle_beta                 100.0910(10)
_cell_angle_gamma                90
_cell_volume                     1549.56(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    31160
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      78.7160
_cell_measurement_theta_min      4.0380
_shelx_estimated_absorpt_T_max   0.926
_shelx_estimated_absorpt_T_min   0.602
_exptl_absorpt_coefficient_mu    1.946
_exptl_absorpt_correction_T_max  0.923
_exptl_absorpt_correction_T_min  0.707
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             736
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 6 0.0078
3 2 -5 0.1023
-5 -1 0 0.1268
5 1 -1 0.1495
0 14 0 0.0222
0 -14 0 0.0222
2 0 -6 0.1301
0 13 -2 0.0558
-1 14 1 0.0330
-2 8 5 0.0387
-5 -1 0 0.1265

_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.04
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
0.1566 -1.2776 5.7214 0.1859 0.3080 0.9330
3.1904 1.6373 -5.1385 0.1691 0.2726 -0.9471
-5.0728 -0.7075 -0.1691 -0.5168 -0.8448 0.1385
5.1746 0.9941 -1.0254 0.4916 0.8027 -0.3377
0.4103 14.0927 -0.1876 -0.7846 0.6003 -0.1552
-0.4103 -14.0927 0.1876 0.7846 -0.6003 0.1552
1.7289 0.2383 -5.7894 0.0804 -0.0521 -0.9954
-0.0059 13.1485 -2.1247 -0.8066 0.3848 -0.4487
-1.0433 13.6775 1.0918 -0.8985 0.4271 0.1015
-1.8685 8.0625 4.6344 -0.6014 0.2842 0.7467
-5.0497 -0.6757 -0.2941 -0.5182 -0.8472 0.1173

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_unetI/netI     0.0147
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            37063
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.905
_diffrn_reflns_theta_min         4.058
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(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 0.956
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     40.00 125.00   0.50    0.21    --   49.96  19.00 120.00  170
  2  ω     62.00 120.00   0.50    0.21    --   49.96 178.00-120.00  116
  3  ω    -26.00  25.00   0.50    0.21    --  -50.71  19.00-150.00  102
  4  ω    -26.00  25.00   0.50    0.21    --  -50.71  19.00 -60.00  102
  5  ω    -43.00  24.00   0.50    0.21    --  -50.71  38.00-180.00  134
  6  ω    -43.00 -11.00   0.50    0.26    --  -86.25  38.00-180.00   64
  7  ω    -43.00 -11.00   0.50    0.26    --  -86.25  38.00  60.00   64
  8  ω    -43.00 -11.00   0.50    0.26    --  -86.25  38.00-150.00   64
  9  ω    -43.00 -11.00   0.50    0.26    --  -86.25  38.00  90.00   64
 10  ω    -43.00 -11.00   0.50    0.26    --  -86.25  38.00-120.00   64
 11  ω    -43.00 -11.00   0.50    0.26    --  -86.25  38.00 150.00   64
 12  ω   -105.00 -22.00   0.50    0.26    --  -86.25  77.00   0.00  166
 13  ω   -158.00 -73.00   0.50    0.26    --  -86.25-125.00  60.00  170
 14  ω     94.00 178.00   0.50    0.26    --  107.75 125.00   0.00  168
 15  ω     39.00 107.00   0.50    0.26    --  107.75 -99.00  90.00  136
 16  ω     37.00  66.00   0.50    0.26    --  107.75 -57.00   0.00   58
 17  ω     37.00  66.00   0.50    0.26    --  107.75 -57.00  30.00   58
 18  ω     97.00 178.00   0.50    0.26    --  107.75  19.00 -60.00  162
 19  ω     39.00 107.00   0.50    0.26    --  107.75 -99.00 150.00  136
 20  ω     37.00  66.00   0.50    0.26    --  107.75 -57.00 -90.00   58
 21  ω     37.00  66.00   0.50    0.26    --  107.75 -57.00-180.00   58
 22  ω     43.00 105.00   0.50    0.26    --  107.75 -77.00  90.00  124
 23  ω     28.00 114.00   0.50    0.21    --   49.96  77.00 120.00  172
 24  ω     28.00 114.00   0.50    0.21    --   49.96  77.00-180.00  172
 25  ω     28.00 114.00   0.50    0.21    --   49.96  77.00   0.00  172
 26  ω   -115.00 -28.00   0.50    0.21    --  -50.71 -77.00  30.00  174
 27  ω   -115.00 -28.00   0.50    0.21    --  -50.71 -77.00 -90.00  174
 28  ω   -161.00 -75.00   0.50    0.26    --  -86.25 -19.00  90.00  172
 29  ω   -151.00 -64.00   0.50    0.26    --  -86.25 -77.00-180.00  174
 30  ω   -161.00 -76.00   0.50    0.26    --  -86.25 -38.00-180.00  170
 31  ω   -151.00 -64.00   0.50    0.26    --  -86.25 -77.00   0.00  174
 32  ω    -43.00 -11.00   0.50    0.26    --  -86.25  38.00 -60.00   64
 33  ω   -151.00 -64.00   0.50    0.26    --  -86.25 -77.00  60.00  174
 34  ω   -151.00 -64.00   0.50    0.26    --  -86.25 -77.00 150.00  174
 35  ω   -151.00 -64.00   0.50    0.26    --  -86.25 -77.00 -60.00  174
 36  ω   -157.00 -71.00   0.50    0.26    --  -86.25 -57.00  90.00  172
 37  ω   -151.00 -64.00   0.50    0.26    --  -86.25 -77.00-120.00  174
 38  ω   -151.00 -64.00   0.50    0.26    --  -86.25 -77.00 -90.00  174
 39  ω   -151.00 -64.00   0.50    0.26    --  -86.25 -77.00 -30.00  174
 40  ω   -151.00 -64.00   0.50    0.26    --  -86.25 -77.00  30.00  174
 41  ω     36.00 112.00   0.50    0.26    --  107.75-125.00  30.00  152
 42  ω     37.00  66.00   0.50    0.26    --  107.75 -57.00-120.00   58
 43  ω     35.00 121.00   0.50    0.21    --   49.96  57.00 120.00  172
 44  ω     35.00 121.00   0.50    0.21    --   49.96  57.00 -90.00  172
 45  ω     35.00 115.00   0.50    0.21    --   49.96  57.00-180.00  160
 46  ω     28.00 114.00   0.50    0.21    --   49.96  77.00 -90.00  172
;
_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      0.1095159000
_diffrn_orient_matrix_UB_12      -0.0586452000
_diffrn_orient_matrix_UB_13      0.0164022000
_diffrn_orient_matrix_UB_21      0.1591964000
_diffrn_orient_matrix_UB_22      0.0387322000
_diffrn_orient_matrix_UB_23      0.0581293000
_diffrn_orient_matrix_UB_31      -0.0316067000
_diffrn_orient_matrix_UB_32      -0.0079336000
_diffrn_orient_matrix_UB_33      0.1621711000
_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                3075
_reflns_number_total             3198
_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         0.213
_refine_diff_density_min         -0.494
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3198
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0293
_refine_ls_R_factor_gt           0.0284
_refine_ls_restrained_S_all      1.066
_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)+(0.0341P)²+0.8163P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0736
_refine_ls_wR_factor_ref         0.0742
_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:
 N1(H1), C13(H13), C7(H7), C14(H14), C8(H8), C6(H6), C4(H4), C3(H3), C11(H11),
 C10(H10)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
2.c Idealised tetrahedral OH refined as rotating group:
 O7(H7A), O2(H2), O6(H6A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.25576(3) 0.00016(2) 0.55373(3) 0.01262(9) Uani 1 1 d . . . . .
O4 O 0.14258(10) 0.03589(4) 0.64043(9) 0.01591(18) Uani 1 1 d . . . . .
O5 O 0.30961(10) 0.03726(4) 0.42789(9) 0.01575(18) Uani 1 1 d . . . . .
O7 O 0.41384(10) -0.02209(4) 0.66787(9) 0.01818(19) Uani 1 1 d . . . . .
H7A H 0.497364 -0.025781 0.623620 0.027 Uiso 1 1 calc R U . . .
O3 O 0.09964(12) 0.73371(4) 0.43706(10) 0.0208(2) Uani 1 1 d . . . . .
O2 O 0.25537(11) 0.15534(4) 0.42354(10) 0.0213(2) Uani 1 1 d . . . . .
H2 H 0.281241 0.118068 0.435328 0.032 Uiso 1 1 calc R U . . .
O6 O 0.16640(11) -0.06061(4) 0.48974(10) 0.01798(19) Uani 1 1 d . . . . .
H6A H 0.066024 -0.052915 0.448538 0.027 Uiso 1 1 calc R U . . .
O1 O 0.48330(12) 0.16811(4) 0.60383(11) 0.0255(2) Uani 1 1 d . . . . .
N1 N 0.24548(12) 0.44527(5) 0.43583(11) 0.0149(2) Uani 1 1 d . . . . .
H1 H 0.205085 0.457163 0.343439 0.018 Uiso 1 1 calc R U . . .
C13 C 0.07245(15) 0.63178(6) 0.36131(13) 0.0169(2) Uani 1 1 d . . . . .
H13 H -0.000403 0.645184 0.272695 0.020 Uiso 1 1 calc R U . . .
C5 C 0.28415(15) 0.38173(5) 0.45819(13) 0.0146(2) Uani 1 1 d . . . . .
C1 C 0.36805(15) 0.18910(6) 0.51328(13) 0.0161(2) Uani 1 1 d . . . . .
C2 C 0.33803(15) 0.25646(5) 0.49097(13) 0.0153(2) Uani 1 1 d . . . . .
C7 C 0.22678(15) 0.27909(6) 0.36691(13) 0.0167(2) Uani 1 1 d . . . . .
H7 H 0.168640 0.251527 0.294105 0.020 Uiso 1 1 calc R U . . .
C12 C 0.14055(15) 0.67465(5) 0.47198(13) 0.0162(2) Uani 1 1 d . . . . .
C9 C 0.21614(15) 0.55017(6) 0.51433(13) 0.0161(2) Uani 1 1 d . . . . .
C14 C 0.11102(15) 0.57077(6) 0.38112(13) 0.0161(2) Uani 1 1 d . . . . .
H14 H 0.066958 0.542099 0.305021 0.019 Uiso 1 1 calc R U . . .
C8 C 0.26448(15) 0.48720(6) 0.53949(13) 0.0172(2) Uani 1 1 d . . . . .
H8 H 0.313741 0.475323 0.638695 0.021 Uiso 1 1 calc R U . . .
C6 C 0.20092(15) 0.34166(5) 0.34967(13) 0.0166(2) Uani 1 1 d . . . . .
H6 H 0.126743 0.357208 0.264208 0.020 Uiso 1 1 calc R U . . .
C4 C 0.39843(15) 0.36019(6) 0.58135(13) 0.0177(2) Uani 1 1 d . . . . .
H4 H 0.457099 0.387873 0.653566 0.021 Uiso 1 1 calc R U . . .
C3 C 0.42473(15) 0.29734(6) 0.59628(14) 0.0177(2) Uani 1 1 d . . . . .
H3 H 0.502870 0.281928 0.679367 0.021 Uiso 1 1 calc R U . . .
C11 C 0.24077(15) 0.65518(6) 0.60599(14) 0.0183(3) Uani 1 1 d . . . . .
H11 H 0.284259 0.684053 0.681767 0.022 Uiso 1 1 calc R U . . .
C10 C 0.27599(16) 0.59324(6) 0.62706(13) 0.0183(3) Uani 1 1 d . . . . .
H10 H 0.341611 0.579639 0.719117 0.022 Uiso 1 1 calc R U . . .
C15 C 0.16818(18) 0.78030(6) 0.54335(15) 0.0241(3) Uani 1 1 d . . . . .
H15A H 0.125464 0.820593 0.506053 0.036 Uiso 1 1 calc R U . . .
H15B H 0.292530 0.779928 0.556300 0.036 Uiso 1 1 calc R U . . .
H15C H 0.133248 0.772128 0.640111 0.036 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
P1 O4 1.5122(8) . ?
P1 O5 1.5180(8) . ?
P1 O7 1.5616(8) . ?
P1 O6 1.5660(9) . ?
O7 H7A 0.8400 . ?
O3 C12 1.3512(14) . ?
O3 C15 1.4386(15) . ?
O2 H2 0.8400 . ?
O2 C1 1.3244(15) . ?
O6 H6A 0.8400 . ?
O1 C1 1.2096(15) . ?
N1 H1 0.8800 . ?
N1 C5 1.4251(15) . ?
N1 C8 1.2984(16) . ?
C13 H13 0.9500 . ?
C13 C12 1.4066(17) . ?
C13 C14 1.3693(17) . ?
C5 C6 1.3922(16) . ?
C5 C4 1.3920(16) . ?
C1 C2 1.4950(16) . ?
C2 C7 1.3935(16) . ?
C2 C3 1.3958(17) . ?
C7 H7 0.9500 . ?
C7 C6 1.3835(17) . ?
C12 C11 1.3961(17) . ?
C9 C14 1.4152(16) . ?
C9 C8 1.4325(17) . ?
C9 C10 1.4062(17) . ?
C14 H14 0.9500 . ?
C8 H8 0.9500 . ?
C6 H6 0.9500 . ?
C4 H4 0.9500 . ?
C4 C3 1.3883(17) . ?
C3 H3 0.9500 . ?
C11 H11 0.9500 . ?
C11 C10 1.3847(17) . ?
C10 H10 0.9500 . ?
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
O4 P1 O5 112.84(5) . . ?
O4 P1 O7 107.78(5) . . ?
O4 P1 O6 110.56(5) . . ?
O5 P1 O7 110.96(5) . . ?
O5 P1 O6 110.13(5) . . ?
O7 P1 O6 104.21(5) . . ?
P1 O7 H7A 109.5 . . ?
C12 O3 C15 117.88(10) . . ?
C1 O2 H2 109.5 . . ?
P1 O6 H6A 109.5 . . ?
C5 N1 H1 117.1 . . ?
C8 N1 H1 117.1 . . ?
C8 N1 C5 125.87(10) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C14 C13 C12 120.09(11) . . ?
C6 C5 N1 116.37(10) . . ?
C4 C5 N1 122.45(11) . . ?
C4 C5 C6 121.18(11) . . ?
O2 C1 C2 112.75(10) . . ?
O1 C1 O2 124.05(11) . . ?
O1 C1 C2 123.20(11) . . ?
C7 C2 C1 121.37(11) . . ?
C7 C2 C3 119.58(11) . . ?
C3 C2 C1 119.05(10) . . ?
C2 C7 H7 120.0 . . ?
C6 C7 C2 120.06(11) . . ?
C6 C7 H7 120.0 . . ?
O3 C12 C13 114.73(10) . . ?
O3 C12 C11 124.80(11) . . ?
C11 C12 C13 120.47(11) . . ?
C14 C9 C8 122.83(11) . . ?
C10 C9 C14 118.74(11) . . ?
C10 C9 C8 118.42(11) . . ?
C13 C14 C9 120.38(11) . . ?
C13 C14 H14 119.8 . . ?
C9 C14 H14 119.8 . . ?
N1 C8 C9 124.40(11) . . ?
N1 C8 H8 117.8 . . ?
C9 C8 H8 117.8 . . ?
C5 C6 H6 120.2 . . ?
C7 C6 C5 119.67(11) . . ?
C7 C6 H6 120.2 . . ?
C5 C4 H4 120.7 . . ?
C3 C4 C5 118.50(11) . . ?
C3 C4 H4 120.7 . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 120.96(11) . . ?
C4 C3 H3 119.5 . . ?
C12 C11 H11 120.4 . . ?
C10 C11 C12 119.17(11) . . ?
C10 C11 H11 120.4 . . ?
C9 C10 H10 119.5 . . ?
C11 C10 C9 121.03(11) . . ?
C11 C10 H10 119.5 . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 C12 C11 C10 -178.86(12) . . . . ?
O2 C1 C2 C7 -12.99(16) . . . . ?
O2 C1 C2 C3 167.58(11) . . . . ?
O1 C1 C2 C7 166.98(12) . . . . ?
O1 C1 C2 C3 -12.45(18) . . . . ?
N1 C5 C6 C7 -177.40(11) . . . . ?
N1 C5 C4 C3 178.20(11) . . . . ?
C13 C12 C11 C10 1.65(18) . . . . ?
C5 N1 C8 C9 -176.65(11) . . . . ?
C5 C4 C3 C2 -0.40(19) . . . . ?
C1 C2 C7 C6 179.68(11) . . . . ?
C1 C2 C3 C4 -178.86(11) . . . . ?
C2 C7 C6 C5 -1.17(18) . . . . ?
C7 C2 C3 C4 1.70(18) . . . . ?
C12 C13 C14 C9 1.52(18) . . . . ?
C12 C11 C10 C9 1.65(19) . . . . ?
C14 C13 C12 O3 177.21(11) . . . . ?
C14 C13 C12 C11 -3.25(18) . . . . ?
C14 C9 C8 N1 13.47(19) . . . . ?
C14 C9 C10 C11 -3.34(18) . . . . ?
C8 N1 C5 C6 157.45(12) . . . . ?
C8 N1 C5 C4 -22.47(18) . . . . ?
C8 C9 C14 C13 -178.26(11) . . . . ?
C8 C9 C10 C11 176.65(12) . . . . ?
C6 C5 C4 C3 -1.71(18) . . . . ?
C4 C5 C6 C7 2.51(18) . . . . ?
C3 C2 C7 C6 -0.90(18) . . . . ?
C10 C9 C14 C13 1.72(18) . . . . ?
C10 C9 C8 N1 -166.51(12) . . . . ?
C15 O3 C12 C13 -178.51(11) . . . . ?
C15 O3 C12 C11 1.98(18) . . . . ?

_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 1.864
_oxdiff_exptl_absorpt_empirical_full_min 0.644
####################################################################### 
# 
# 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_ps010
_database_code_depnum_ccdc_archive 'CCDC 2285252'
loop_
_audit_author_name
_audit_author_address
'Paulina Sobczak'
;Lodz University of Technology
Poland
;
_audit_update_record             
;
2023-07-28 deposited with the CCDC.	2023-10-25 downloaded from the CCDC.
;
_audit_creation_date             2022-12-06
_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 H13 N O3'
_chemical_formula_sum            'C15 H13 N O3'
_chemical_formula_weight         255.26
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C15 H13 N1 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      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                   3.89223(4)
_cell_length_b                   10.76523(10)
_cell_length_c                   15.40737(14)
_cell_angle_alpha                109.0366(8)
_cell_angle_beta                 94.0110(8)
_cell_angle_gamma                90.8565(8)
_cell_volume                     608.291(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    24606
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      78.5470
_cell_measurement_theta_min      4.3220
_shelx_estimated_absorpt_T_max   0.939
_shelx_estimated_absorpt_T_min   0.837
_exptl_absorpt_coefficient_mu    0.803
_exptl_absorpt_correction_T_max  0.948
_exptl_absorpt_correction_T_min  0.880
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             268
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -7 2 0.0737
-2 -1 1 0.0908
0 7 -2 0.0902
2 1 -1 0.1024
0 -3 -7 0.0402
0 3 7 0.0402
-2 -1 5 0.0771
2 3 1 0.0729
2 1 -6 0.0800
0 6 -6 0.0886
0 -7 6 0.0701
-1 4 -9 0.0842
2 5 -6 0.0819
0 1 9 0.0286

_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.165
_exptl_crystal_size_min          0.08
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
-0.0936 -6.8800 1.6747 -0.2069 -0.8607 -0.4651
-2.4737 -1.2924 0.9667 0.0535 0.2335 -0.9709
-0.3801 6.8271 -1.5363 0.2231 0.9302 0.2914
2.4872 1.0936 -0.8799 -0.0643 -0.2593 0.9637
0.0111 -2.7341 -7.3957 0.7053 -0.6687 -0.2354
-0.0111 2.7341 7.3957 -0.7053 0.6687 0.2354
-2.2093 -1.2431 5.4397 -0.4016 0.3777 -0.8343
1.9477 3.4352 1.4943 -0.2462 0.2362 0.9400
2.1459 0.9945 -5.8564 0.4448 -0.4187 0.7917
-0.3993 6.4997 -6.1093 0.6704 0.7071 0.2247
-0.1194 -6.6581 5.9557 -0.6235 -0.6569 -0.4240
-0.7680 3.8163 -8.9462 0.9532 0.2831 -0.1064
1.5584 4.7442 -6.2838 0.5506 0.1656 0.8182
0.0321 1.2926 8.6458 -0.8408 0.5146 0.1682

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_unetI/netI     0.0139
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            33767
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.744
_diffrn_reflns_theta_min         4.348
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_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 0.977
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -60.00  25.00   0.50    0.31    --  -49.71  38.00   0.00  170
  2  ω    -72.00  15.00   0.50    0.31    --  -49.71  77.00   0.00  174
  3  ω    -71.00 -11.00   0.50    0.44    --  -86.25  38.00-120.00  120
  4  ω    -92.00 -16.00   0.50    0.44    --  -86.25 125.00 -60.00  152
  5  ω    -97.00 -11.00   0.50    0.44    --  -86.25  19.00-180.00  172
  6  ω    -96.00 -15.00   0.50    0.44    --  -86.25  57.00 -60.00  162
  7  ω   -121.00 -35.00   0.50    0.31    --  -49.71 -57.00-150.00  172
  8  ω     59.00 120.00   0.50    0.31    --   49.71 178.00-120.00  122
  9  ω     85.00 173.00   0.50    0.44    --  107.75  77.00 -90.00  176
 10  ω     98.00 178.00   0.50    0.44    --  107.75  38.00  30.00  160
 11  ω     98.00 178.00   0.50    0.44    --  107.75  38.00 -30.00  160
 12  ω     98.00 178.00   0.50    0.44    --  107.75  38.00 -90.00  160
 13  ω     85.00 173.00   0.50    0.44    --  107.75  77.00  60.00  176
 14  ω     91.00 178.00   0.50    0.44    --  107.75 125.00 150.00  174
 15  ω     98.00 178.00   0.50    0.44    --  107.75  38.00 150.00  160
 16  ω     93.00 178.00   0.50    0.44    --  107.75  57.00  90.00  170
 17  ω     85.00 173.00   0.50    0.44    --  107.75  77.00 -60.00  176
 18  ω     93.00 178.00   0.50    0.44    --  107.75  57.00-180.00  170
 19  ω     85.00 173.00   0.50    0.44    --  107.75  77.00-180.00  176
 20  ω     85.00 173.00   0.50    0.44    --  107.75  77.00-150.00  176
 21  ω     85.00 173.00   0.50    0.44    --  107.75  77.00   0.00  176
 22  ω     39.00 110.00   0.50    0.44    --  107.75 -99.00-150.00  142
 23  ω     33.00  71.00   0.50    0.44    --  107.75 -38.00 -30.00   76
 24  ω     37.00  96.00   0.50    0.44    --  107.75 -57.00  30.00  118
 25  ω     39.00 110.00   0.50    0.44    --  107.75 -99.00  60.00  142
 26  ω     38.00 117.00   0.50    0.44    --  107.75-125.00 120.00  158
 27  ω     39.00 110.00   0.50    0.44    --  107.75 -99.00 150.00  142
 28  ω     37.00 165.00   0.50    0.44    --  107.75   0.00  60.00  256
 29  ω     33.00  71.00   0.50    0.44    --  107.75 -38.00 -60.00   76
 30  ω     33.00  71.00   0.50    0.44    --  107.75 -38.00 -90.00   76
 31  ω     39.00 110.00   0.50    0.44    --  107.75 -99.00 -60.00  142
 32  ω     38.00 117.00   0.50    0.44    --  107.75-125.00-150.00  158
 33  ω     37.00  96.00   0.50    0.44    --  107.75 -57.00 -60.00  118
 34  ω     33.00  71.00   0.50    0.44    --  107.75 -38.00-120.00   76
 35  ω     37.00 165.00   0.50    0.44    --  107.75   0.00 -60.00  256
 36  ω     37.00 165.00   0.50    0.44    --  107.75   0.00  30.00  256
 37  ω     37.00 165.00   0.50    0.44    --  107.75   0.00 -30.00  256
 38  ω     37.00 165.00   0.50    0.44    --  107.75   0.00 -90.00  256
 39  ω     37.00 165.00   0.50    0.44    --  107.75   0.00-120.00  256
 40  ω     37.00 165.00   0.50    0.44    --  107.75   0.00-150.00  256
 41  ω     37.00 165.00   0.50    0.44    --  107.75   0.00   0.00  256
 42  ω     37.00 165.00   0.50    0.44    --  107.75   0.00-180.00  256
 43  ω     40.00 124.00   0.50    0.31    --   49.71  38.00 -90.00  168
 44  ω     37.00 165.00   0.50    0.44    --  107.75   0.00  90.00  256
 45  ω     37.00 165.00   0.50    0.44    --  107.75   0.00 120.00  256
 46  ω     27.00 115.00   0.50    0.31    --   49.71  77.00-120.00  176
 47  ω     27.00 115.00   0.50    0.31    --   49.71  77.00  60.00  176
 48  ω     27.00 115.00   0.50    0.31    --   49.71  77.00 150.00  176
 49  ω     27.00 115.00   0.50    0.31    --   49.71  77.00 -30.00  176
 50  ω     27.00 115.00   0.50    0.31    --   49.71  77.00  30.00  176
 51  ω     27.00 115.00   0.50    0.31    --   49.71  77.00 120.00  176
 52  ω   -120.00 -70.00   0.50    0.31    --  -49.71-125.00 -61.00  100
 53  ω   -121.00 -35.00   0.50    0.31    --  -49.71 -57.00 -30.00  172
 54  ω   -124.00 -39.00   0.50    0.31    --  -49.71 -38.00  60.00  170
 55  ω   -121.00 -35.00   0.50    0.31    --  -49.71 -57.00 150.00  172
 56  ω   -124.00 -39.00   0.50    0.31    --  -49.71 -38.00   0.00  170
 57  ω   -121.00 -35.00   0.50    0.31    --  -49.71 -57.00 -90.00  172
 58  ω   -121.00 -35.00   0.50    0.31    --  -49.71 -57.00 -60.00  172
 59  ω   -125.00 -38.00   0.50    0.31    --  -49.71 -19.00-180.00  174
 60  ω   -151.00 -64.00   0.50    0.44    --  -86.25 -77.00-180.00  174
 61  ω   -151.00 -64.00   0.50    0.44    --  -86.25 -77.00   0.00  174
 62  ω   -124.00 -39.00   0.50    0.31    --  -49.71 -38.00 150.00  170
 63  ω   -157.00 -71.00   0.50    0.44    --  -86.25 -57.00  90.00  172
 64  ω   -151.00 -64.00   0.50    0.44    --  -86.25 -77.00  60.00  174
 65  ω   -157.00 -71.00   0.50    0.44    --  -86.25 -57.00 120.00  172
 66  ω   -151.00 -64.00   0.50    0.44    --  -86.25 -77.00  30.00  174
 67  ω   -157.00 -71.00   0.50    0.44    --  -86.25 -57.00  30.00  172
 68  ω   -151.00 -64.00   0.50    0.44    --  -86.25 -77.00 -90.00  174
 69  ω   -151.00 -64.00   0.50    0.44    --  -86.25 -77.00-150.00  174
 70  ω   -151.00 -64.00   0.50    0.44    --  -86.25 -77.00 -30.00  174
 71  ω   -151.00 -64.00   0.50    0.44    --  -86.25 -77.00 -60.00  174
 72  ω   -151.00 -64.00   0.50    0.44    --  -86.25 -77.00 120.00  174
 73  ω   -151.00 -64.00   0.50    0.44    --  -86.25 -77.00 150.00  174
 74  ω   -151.00 -64.00   0.50    0.44    --  -86.25 -77.00  90.00  174
 75  ω   -157.00 -71.00   0.50    0.44    --  -86.25 -57.00 150.00  172
 76  ω   -161.00 -75.00   0.50    0.44    --  -86.25 -19.00 120.00  172
 77  ω   -161.00 -76.00   0.50    0.44    --  -86.25 -38.00 120.00  170
 78  ω   -157.00 -71.00   0.50    0.44    --  -86.25 -57.00 -90.00  172
 79  ω   -151.00 -64.00   0.50    0.44    --  -86.25 -77.00-120.00  174
 80  ω   -157.00 -71.00   0.50    0.44    --  -86.25 -57.00-180.00  172
 81  ω   -161.00 -75.00   0.50    0.44    --  -86.25 -19.00-120.00  172
 82  ω   -161.00 -75.00   0.50    0.44    --  -86.25 -19.00-150.00  172
;
_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      -0.0636443000
_diffrn_orient_matrix_UB_12      0.0070630000
_diffrn_orient_matrix_UB_13      -0.0980682000
_diffrn_orient_matrix_UB_21      -0.1503870000
_diffrn_orient_matrix_UB_22      0.1367979000
_diffrn_orient_matrix_UB_23      0.0396238000
_diffrn_orient_matrix_UB_31      0.3619629000
_diffrn_orient_matrix_UB_32      0.0647345000
_diffrn_orient_matrix_UB_33      0.0084342000
_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                2383
_reflns_number_total             2543
_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         0.241
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2543
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0337
_refine_ls_restrained_S_all      1.086
_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)+(0.0484P)²+0.1845P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0934
_refine_ls_wR_factor_ref         0.0944
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C6(H6), C13(H13), C4(H4), C11(H11), C8(H8), C14(H14), C10(H10)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 1.2632(2) 0.50489(7) 0.91553(5) 0.02012(18) Uani 1 1 d . . . . .
O1 O 0.2518(2) 0.11431(7) 0.07673(5) 0.02314(19) Uani 1 1 d . . . . .
O2 O 0.0417(2) -0.07272(7) 0.09039(5) 0.02302(19) Uani 1 1 d . . . . .
H2 H -0.046004 -0.082673 0.037048 0.035 Uiso 1 1 calc R U . . .
N1 N 0.7589(2) 0.18837(8) 0.49560(6) 0.0185(2) Uani 1 1 d . . . . .
C9 C 0.8779(3) 0.36016(10) 0.64188(7) 0.0172(2) Uani 1 1 d . . . . .
C3 C 0.5652(3) 0.19147(10) 0.25683(7) 0.0172(2) Uani 1 1 d . . . . .
H3 H 0.609623 0.245023 0.220243 0.021 Uiso 1 1 calc R U . . .
C12 C 1.1271(3) 0.46403(10) 0.82691(7) 0.0168(2) Uani 1 1 d . . . . .
C2 C 0.3698(3) 0.07415(9) 0.21831(7) 0.0169(2) Uani 1 1 d . . . . .
C7 C 0.3124(3) -0.00565(10) 0.27197(7) 0.0181(2) Uani 1 1 d . . . . .
H7 H 0.183523 -0.086553 0.245667 0.022 Uiso 1 1 calc R U . . .
C6 C 0.4423(3) 0.03251(10) 0.36330(7) 0.0188(2) Uani 1 1 d . . . . .
H6 H 0.404658 -0.022718 0.399134 0.023 Uiso 1 1 calc R U . . .
C13 C 1.1902(3) 0.33356(10) 0.77530(7) 0.0185(2) Uani 1 1 d . . . . .
H13 H 1.317184 0.280258 0.803444 0.022 Uiso 1 1 calc R U . . .
C4 C 0.6948(3) 0.23034(10) 0.34804(7) 0.0180(2) Uani 1 1 d . . . . .
H4 H 0.828879 0.310112 0.373690 0.022 Uiso 1 1 calc R U . . .
C11 C 0.9388(3) 0.54239(10) 0.78606(7) 0.0172(2) Uani 1 1 d . . . . .
H11 H 0.894663 0.630619 0.820562 0.021 Uiso 1 1 calc R U . . .
C5 C 0.6287(3) 0.15231(10) 0.40276(7) 0.0173(2) Uani 1 1 d . . . . .
C8 C 0.7358(3) 0.30816(10) 0.54634(7) 0.0182(2) Uani 1 1 d . . . . .
H8 H 0.619824 0.366314 0.520355 0.022 Uiso 1 1 calc R U . . .
C14 C 1.0687(3) 0.28272(10) 0.68423(7) 0.0181(2) Uani 1 1 d . . . . .
H14 H 1.114066 0.194650 0.649658 0.022 Uiso 1 1 calc R U . . .
C1 C 0.2183(3) 0.04009(10) 0.12235(7) 0.0175(2) Uani 1 1 d . . . . .
C15 C 1.1997(3) 0.63668(10) 0.97153(7) 0.0203(2) Uani 1 1 d . . . . .
H15A H 1.300340 0.699091 0.945254 0.030 Uiso 1 1 calc R U . . .
H15B H 1.304847 0.653034 1.034131 0.030 Uiso 1 1 calc R U . . .
H15C H 0.950679 0.647909 0.973454 0.030 Uiso 1 1 calc R U . . .
C10 C 0.8167(3) 0.48924(10) 0.69397(7) 0.0179(2) Uani 1 1 d . . . . .
H10 H 0.688405 0.542287 0.665874 0.021 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 C12 1.3559(12) . ?
O3 C15 1.4354(12) . ?
O1 C1 1.2352(12) . ?
O2 H2 0.8400 . ?
O2 C1 1.3144(12) . ?
N1 C5 1.4085(13) . ?
N1 C8 1.2798(13) . ?
C9 C8 1.4580(14) . ?
C9 C14 1.4064(14) . ?
C9 C10 1.3931(14) . ?
C3 H3 0.9500 . ?
C3 C2 1.3947(14) . ?
C3 C4 1.3841(14) . ?
C12 C13 1.4051(14) . ?
C12 C11 1.3948(14) . ?
C2 C7 1.3982(14) . ?
C2 C1 1.4784(13) . ?
C7 H7 0.9500 . ?
C7 C6 1.3862(14) . ?
C6 H6 0.9500 . ?
C6 C5 1.3995(15) . ?
C13 H13 0.9500 . ?
C13 C14 1.3749(14) . ?
C4 H4 0.9500 . ?
C4 C5 1.4029(14) . ?
C11 H11 0.9500 . ?
C11 C10 1.3908(14) . ?
C8 H8 0.9500 . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C10 H10 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
C12 O3 C15 117.46(8) . . ?
C1 O2 H2 109.5 . . ?
C8 N1 C5 117.94(8) . . ?
C14 C9 C8 121.94(9) . . ?
C10 C9 C8 119.42(9) . . ?
C10 C9 C14 118.62(9) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C4 C3 C2 120.38(9) . . ?
O3 C12 C13 115.44(9) . . ?
O3 C12 C11 124.48(9) . . ?
C11 C12 C13 120.08(9) . . ?
C3 C2 C7 119.47(9) . . ?
C3 C2 C1 118.71(9) . . ?
C7 C2 C1 121.78(9) . . ?
C2 C7 H7 119.8 . . ?
C6 C7 C2 120.43(9) . . ?
C6 C7 H7 119.8 . . ?
C7 C6 H6 120.0 . . ?
C7 C6 C5 120.06(9) . . ?
C5 C6 H6 120.0 . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.26(9) . . ?
C14 C13 H13 119.9 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.22(9) . . ?
C5 C4 H4 119.9 . . ?
C12 C11 H11 120.5 . . ?
C10 C11 C12 118.91(9) . . ?
C10 C11 H11 120.5 . . ?
C6 C5 N1 118.85(9) . . ?
C6 C5 C4 119.38(9) . . ?
C4 C5 N1 121.70(9) . . ?
N1 C8 C9 123.51(9) . . ?
N1 C8 H8 118.2 . . ?
C9 C8 H8 118.2 . . ?
C9 C14 H14 119.8 . . ?
C13 C14 C9 120.48(9) . . ?
C13 C14 H14 119.8 . . ?
O1 C1 O2 122.93(9) . . ?
O1 C1 C2 121.82(9) . . ?
O2 C1 C2 115.23(8) . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C9 C10 H10 119.2 . . ?
C11 C10 C9 121.66(9) . . ?
C11 C10 H10 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
O3 C12 C13 C14 -178.92(9) . . . . ?
O3 C12 C11 C10 179.11(9) . . . . ?
C3 C2 C7 C6 1.32(15) . . . . ?
C3 C2 C1 O1 -2.17(15) . . . . ?
C3 C2 C1 O2 179.10(9) . . . . ?
C3 C4 C5 N1 179.48(9) . . . . ?
C3 C4 C5 C6 2.48(15) . . . . ?
C12 C13 C14 C9 -0.52(16) . . . . ?
C12 C11 C10 C9 0.01(15) . . . . ?
C2 C3 C4 C5 -0.40(15) . . . . ?
C2 C7 C6 C5 0.77(15) . . . . ?
C7 C2 C1 O1 175.61(10) . . . . ?
C7 C2 C1 O2 -3.12(14) . . . . ?
C7 C6 C5 N1 -179.75(9) . . . . ?
C7 C6 C5 C4 -2.66(15) . . . . ?
C13 C12 C11 C10 -0.16(15) . . . . ?
C4 C3 C2 C7 -1.50(15) . . . . ?
C4 C3 C2 C1 176.33(9) . . . . ?
C11 C12 C13 C14 0.42(16) . . . . ?
C5 N1 C8 C9 -176.29(9) . . . . ?
C8 N1 C5 C6 -138.35(10) . . . . ?
C8 N1 C5 C4 44.63(14) . . . . ?
C8 C9 C14 C13 -177.98(9) . . . . ?
C8 C9 C10 C11 178.28(9) . . . . ?
C14 C9 C8 N1 3.37(16) . . . . ?
C14 C9 C10 C11 -0.11(15) . . . . ?
C1 C2 C7 C6 -176.44(9) . . . . ?
C15 O3 C12 C13 -178.78(9) . . . . ?
C15 O3 C12 C11 1.92(14) . . . . ?
C10 C9 C8 N1 -174.97(10) . . . . ?
C10 C9 C14 C13 0.37(15) . . . . ?

_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 1.440
_oxdiff_exptl_absorpt_empirical_full_min 0.697
####################################################################### 
# 
# 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_ps010-no3pl
_database_code_depnum_ccdc_archive 'CCDC 2285249'
loop_
_audit_author_name
_audit_author_address
'Paulina Sobczak'
;Lodz University of Technology
Poland
;
_audit_update_record             
;
2023-07-28 deposited with the CCDC.	2023-10-25 downloaded from the CCDC.
;
_audit_creation_date             2022-12-06
_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 H13 N O3'
_chemical_formula_sum            'C15 H13 N O3'
_chemical_formula_weight         255.26
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C15 H13 N1 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                   3.82566(3)
_cell_length_b                   15.07160(6)
_cell_length_c                   21.19950(9)
_cell_angle_alpha                90
_cell_angle_beta                 92.4431(5)
_cell_angle_gamma                90
_cell_volume                     1221.225(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    68442
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      78.7130
_cell_measurement_theta_min      3.5740
_shelx_estimated_absorpt_T_max   0.934
_shelx_estimated_absorpt_T_min   0.843
_exptl_absorpt_coefficient_mu    0.800
_exptl_absorpt_correction_T_max  0.945
_exptl_absorpt_correction_T_min  0.865
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             536
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -10 -2 0.0861
2 0 -1 0.1068
-2 0 1 0.1068
0 10 2 0.1095
0 1 -14 0.0492
0 -1 14 0.0328
2 0 10 0.0626
2 1 5 0.0903
-2 0 -9 0.1012
0 5 12 0.0523
0 -5 -12 0.0730

_exptl_crystal_size_max          0.221
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.086
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
-0.0824 -9.7101 -1.5961 -0.2287 -0.9550 -0.1888
2.4830 0.0169 -0.5500 -0.0333 -0.1504 0.9881
-2.4830 -0.0169 0.5500 0.0333 0.1504 -0.9881
-0.0142 9.7155 1.6185 0.2302 0.9615 0.1504
0.0796 1.1957 -13.6580 0.9722 -0.2324 0.0274
0.0339 -1.1270 13.6485 -0.9725 0.2323 0.0188
1.6177 0.1217 10.0473 -0.7284 0.1725 0.6631
2.2633 0.9345 4.9652 -0.3715 0.0866 0.9244
-1.7657 -0.2777 -9.2423 0.6722 -0.1589 -0.7231
0.0858 4.8665 11.8964 -0.6444 0.7534 0.1311
0.0614 -4.8040 -11.9858 0.6484 -0.7579 -0.0717

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0490
_diffrn_reflns_av_unetI/netI     0.0109
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            85187
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.910
_diffrn_reflns_theta_min         3.599
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(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 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -25.00  26.00   0.50    0.10    --   49.71 -19.00-180.00  102
  2  ω    -43.00  24.00   0.50    0.10    --  -50.71  38.00 -60.00  134
  3  ω    -26.00  25.00   0.50    0.10    --  -50.71  19.00   0.00  102
  4  ω    -26.00  25.00   0.50    0.10    --  -50.71  19.00 150.00  102
  5  ω    -26.00  25.00   0.50    0.10    --  -50.71  19.00-120.00  102
  6  ω    -26.00  25.00   0.50    0.10    --  -50.71  19.00-150.00  102
  7  ω    -43.00 -11.00   0.50    0.22    --  -86.25  38.00 -60.00   64
  8  ω    -43.00 -11.00   0.50    0.22    --  -86.25  38.00  60.00   64
  9  ω    -43.00 -11.00   0.50    0.22    --  -86.25  38.00  90.00   64
 10  ω   -158.00 -73.00   0.50    0.22    --  -86.25-125.00  30.00  170
 11  ω    -43.00 -11.00   0.50    0.22    --  -86.25  38.00  30.00   64
 12  ω    -43.00 -11.00   0.50    0.22    --  -86.25  38.00 -30.00   64
 13  ω     39.00 107.00   0.50    0.22    --  107.75 -99.00 -60.00  136
 14  ω     39.00 107.00   0.50    0.22    --  107.75 -99.00 120.00  136
 15  ω     38.00 117.00   0.50    0.22    --  107.75-132.00 -55.00  158
 16  ω     37.00  66.00   0.50    0.22    --  107.75 -57.00 -60.00   58
 17  ω     43.00 105.00   0.50    0.22    --  107.75 -77.00 120.00  124
 18  ω     97.00 178.00   0.50    0.22    --  107.75  19.00-150.00  162
 19  ω     37.00  66.00   0.50    0.22    --  107.75 -57.00 -90.00   58
 20  ω     27.00 114.00   0.50    0.10    --   49.71  77.00 150.00  174
 21  ω     27.00 114.00   0.50    0.10    --   49.71  77.00 -60.00  174
 22  ω     60.00 121.00   0.50    0.10    --   49.71-178.00-180.00  122
 23  ω     27.00 114.00   0.50    0.10    --   49.71  77.00  30.00  174
 24  ω   -115.00 -28.00   0.50    0.10    --  -50.71 -77.00 -90.00  174
 25  ω   -157.00 -71.00   0.50    0.22    --  -86.25 -57.00 -30.00  172
 26  ω   -151.00 -64.00   0.50    0.22    --  -86.25 -77.00 -60.00  174
 27  ω   -151.00 -64.00   0.50    0.22    --  -86.25 -77.00 120.00  174
 28  ω   -151.00 -64.00   0.50    0.22    --  -86.25 -77.00  30.00  174
 29  ω   -151.00 -64.00   0.50    0.22    --  -86.25 -77.00-180.00  174
 30  ω   -151.00 -64.00   0.50    0.22    --  -86.25 -77.00-120.00  174
 31  ω     97.00 178.00   0.50    0.22    --  107.75  38.00 -90.00  162
 32  ω     37.00 165.00   0.50    0.22    --  107.75   0.00 120.00  256
 33  ω     37.00  66.00   0.50    0.22    --  107.75 -57.00-180.00   58
 34  ω     39.00 107.00   0.50    0.22    --  107.75 -99.00  30.00  136
 35  ω     27.00 114.00   0.50    0.10    --   49.71  77.00 120.00  174
 36  ω     27.00 114.00   0.50    0.10    --   49.71  77.00-150.00  174
 37  ω     35.00 121.00   0.50    0.10    --   49.71  57.00 -60.00  172
 38  ω   -115.00 -28.00   0.50    0.10    --  -50.71 -77.00  30.00  174
 39  ω   -125.00 -40.00   0.50    0.10    --  -50.71 -38.00 150.00  170
 40  ω   -151.00 -64.00   0.50    0.22    --  -86.25 -77.00  60.00  174
 41  ω   -151.00 -64.00   0.50    0.22    --  -86.25 -77.00-150.00  174
 42  ω   -151.00 -64.00   0.50    0.22    --  -86.25 -77.00   0.00  174
 43  ω    -43.00 -11.00   0.50    0.22    --  -86.25  38.00 120.00   64
 44  ω   -151.00 -64.00   0.50    0.22    --  -86.25 -77.00  90.00  174
 45  ω   -151.00 -64.00   0.50    0.22    --  -86.25 -77.00 150.00  174
 46  ω   -151.00 -64.00   0.50    0.22    --  -86.25 -77.00 -90.00  174
 47  ω     43.00 105.00   0.50    0.22    --  107.75 -77.00   0.00  124
 48  ω     37.00  66.00   0.50    0.22    --  107.75 -57.00  30.00   58
 49  ω     37.00  66.00   0.50    0.22    --  107.75 -57.00 150.00   58
 50  ω     62.00 120.00   0.50    0.10    --   49.71 178.00  60.00  116
 51  ω   -125.00 -40.00   0.50    0.10    --  -50.71 -38.00 -90.00  170
 52  ω   -115.00 -28.00   0.50    0.10    --  -50.71 -77.00 120.00  174
 53  ω   -125.00 -40.00   0.50    0.10    --  -50.71 -38.00  60.00  170
 54  ω   -125.00 -40.00   0.50    0.10    --  -50.71 -38.00-180.00  170
 55  ω   -151.00 -64.00   0.50    0.22    --  -86.25 -77.00 -30.00  174
 56  ω     37.00  66.00   0.50    0.22    --  107.75 -57.00  90.00   58
 57  ω     85.00 172.00   0.50    0.22    --  107.75  77.00  60.00  174
 58  ω     94.00 178.00   0.50    0.22    --  107.75 125.00 -30.00  168
 59  ω     85.00 172.00   0.50    0.22    --  107.75  77.00 -30.00  174
 60  ω     37.00  66.00   0.50    0.22    --  107.75 -57.00 120.00   58
 61  ω     39.00 107.00   0.50    0.22    --  107.75 -99.00  60.00  136
 62  ω     85.00 172.00   0.50    0.22    --  107.75  77.00-150.00  174
 63  ω     85.00 172.00   0.50    0.22    --  107.75  77.00  30.00  174
 64  ω     85.00 172.00   0.50    0.22    --  107.75  77.00 120.00  174
 65  ω     35.00 121.00   0.50    0.10    --   49.71  57.00 120.00  172
 66  ω     35.00 121.00   0.50    0.10    --   49.71  57.00 -30.00  172
 67  ω     35.00 121.00   0.50    0.10    --   49.71  57.00  30.00  172
 68  ω     39.00 124.00   0.50    0.10    --   49.71  38.00 -60.00  170
 69  ω   -125.00 -40.00   0.50    0.10    --  -50.71 -38.00-120.00  170
 70  ω   -157.00 -71.00   0.50    0.22    --  -86.25 -57.00  30.00  172
 71  ω   -161.00 -76.00   0.50    0.22    --  -86.25 -38.00-150.00  170
 72  ω   -157.00 -71.00   0.50    0.22    --  -86.25 -57.00-180.00  172
 73  ω   -157.00 -71.00   0.50    0.22    --  -86.25 -57.00   0.00  172
 74  ω   -158.00 -73.00   0.50    0.22    --  -86.25-125.00-150.00  170
 75  ω   -161.00 -76.00   0.50    0.22    --  -86.25 -38.00 -90.00  170
 76  ω     43.00 105.00   0.50    0.22    --  107.75 -77.00 -60.00  124
 77  ω     93.00 178.00   0.50    0.22    --  107.75  57.00-180.00  170
 78  ω     37.00  66.00   0.50    0.22    --  107.75 -57.00-150.00   58
 79  ω     85.00 172.00   0.50    0.22    --  107.75  77.00  90.00  174
 80  ω     35.00 121.00   0.50    0.10    --   49.71  57.00-180.00  172
 81  ω    -25.00  26.00   0.50    0.10    --   49.71 -19.00 150.00  102
 82  ω   -125.00 -40.00   0.50    0.10    --  -50.71 -38.00  30.00  170
 83  ω   -115.00 -28.00   0.50    0.10    --  -50.71 -77.00 -30.00  174
 84  ω   -125.00 -40.00   0.50    0.10    --  -50.71 -38.00-150.00  170
 85  ω   -157.00 -71.00   0.50    0.22    --  -86.25 -57.00 120.00  172
 86  ω     93.00 178.00   0.50    0.22    --  107.75  57.00  60.00  170
 87  ω     37.00 165.00   0.50    0.22    --  107.75   0.00-180.00  256
 88  ω     93.00 178.00   0.50    0.22    --  107.75  57.00 -60.00  170
 89  ω     85.00 172.00   0.50    0.22    --  107.75  77.00   0.00  174
 90  ω     85.00 172.00   0.50    0.22    --  107.75  77.00 -90.00  174
 91  ω     37.00 165.00   0.50    0.22    --  107.75   0.00-150.00  256
 92  ω     37.00 165.00   0.50    0.22    --  107.75   0.00-120.00  256
 93  ω     37.00 165.00   0.50    0.22    --  107.75   0.00 -90.00  256
 94  ω     85.00 172.00   0.50    0.22    --  107.75  77.00-120.00  174
 95  ω   -122.00 -36.00   0.50    0.10    --  -50.71 -57.00  90.00  172
 96  ω   -126.00 -40.00   0.50    0.10    --  -50.71 -19.00  90.00  172
 97  ω   -126.00 -40.00   0.50    0.10    --  -50.71 -19.00 -90.00  172
 98  ω   -126.00 -40.00   0.50    0.10    --  -50.71 -19.00  30.00  172
 99  ω   -126.00 -40.00   0.50    0.10    --  -50.71 -19.00 -30.00  172
100  ω     37.00 165.00   0.50    0.22    --  107.75   0.00 -30.00  256
101  ω     37.00 165.00   0.50    0.22    --  107.75   0.00 150.00  256
102  ω     37.00 165.00   0.50    0.22    --  107.75   0.00 -60.00  256
103  ω     37.00 165.00   0.50    0.22    --  107.75   0.00  90.00  256
104  ω     37.00 165.00   0.50    0.22    --  107.75   0.00  60.00  256
105  ω     37.00 165.00   0.50    0.22    --  107.75   0.00  30.00  256
106  ω     37.00 165.00   0.50    0.22    --  107.75   0.00-180.00  256
107  ω     37.00 165.00   0.50    0.22    --  107.75   0.00-150.00  256
108  ω     37.00 165.00   0.50    0.22    --  107.75   0.00-120.00  256
109  ω     37.00 165.00   0.50    0.22    --  107.75   0.00   0.00  256
110  ω    -21.00 106.00   0.50    0.10    --   49.71   0.00-180.00  254
111  ω    -21.00 106.00   0.50    0.10    --   49.71   0.00 -60.00  254
112  ω   -115.00 -28.00   0.50    0.10    --  -50.71 -77.00  60.00  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      -0.0287775000
_diffrn_orient_matrix_UB_12      0.0350233000
_diffrn_orient_matrix_UB_13      -0.0682860000
_diffrn_orient_matrix_UB_21      -0.0556721000
_diffrn_orient_matrix_UB_22      0.0947184000
_diffrn_orient_matrix_UB_23      0.0249828000
_diffrn_orient_matrix_UB_31      0.3981935000
_diffrn_orient_matrix_UB_32      0.0157831000
_diffrn_orient_matrix_UB_33      0.0016933000
_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                2533
_reflns_number_total             2622
_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         0.247
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2622
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0346
_refine_ls_R_factor_gt           0.0339
_refine_ls_restrained_S_all      1.057
_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)+(0.0432P)²+0.4861P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0887
_refine_ls_wR_factor_ref         0.0893
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C7(H7), C6(H6), C4(H4), C14(H14), C13(H13), C3(H3), C8(H8)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 0.5969(2) 0.13698(5) 0.72128(3) 0.02125(18) Uani 1 1 d . . . . .
O1 O 0.8309(2) 0.94148(5) 0.56585(4) 0.0267(2) Uani 1 1 d . . . . .
H1 H 0.869709 0.991866 0.550729 0.040 Uiso 1 1 calc R U . . .
O2 O 1.0470(2) 0.89793(5) 0.47433(4) 0.02499(19) Uani 1 1 d . . . . .
N1 N 0.7370(2) 0.52120(6) 0.59710(4) 0.01749(19) Uani 1 1 d . . . . .
C5 C 0.7898(3) 0.61119(6) 0.58251(4) 0.0158(2) Uani 1 1 d . . . . .
C12 C 0.6302(3) 0.22318(6) 0.70204(5) 0.0167(2) Uani 1 1 d . . . . .
C10 C 0.8563(3) 0.36769(7) 0.72961(5) 0.0172(2) Uani 1 1 d . . . . .
H10 H 0.974299 0.405907 0.759110 0.021 Uiso 1 1 calc R U . . .
C11 C 0.8020(3) 0.27972(7) 0.74523(5) 0.0177(2) Uani 1 1 d . . . . .
H11 H 0.881614 0.257877 0.785347 0.021 Uiso 1 1 calc R U . . .
C7 C 0.9823(3) 0.71917(7) 0.50769(4) 0.0166(2) Uani 1 1 d . . . . .
H7 H 1.087924 0.732853 0.469119 0.020 Uiso 1 1 calc R U . . .
C6 C 0.9397(3) 0.63151(6) 0.52505(4) 0.0169(2) Uani 1 1 d . . . . .
H6 H 1.011701 0.585195 0.498120 0.020 Uiso 1 1 calc R U . . .
C4 C 0.6780(3) 0.67981(7) 0.62141(4) 0.0166(2) Uani 1 1 d . . . . .
H4 H 0.574607 0.666228 0.660213 0.020 Uiso 1 1 calc R U . . .
C9 C 0.7390(3) 0.40090(6) 0.67069(4) 0.0160(2) Uani 1 1 d . . . . .
C14 C 0.5609(3) 0.34364(7) 0.62863(5) 0.0169(2) Uani 1 1 d . . . . .
H14 H 0.475364 0.365786 0.588949 0.020 Uiso 1 1 calc R U . . .
C13 C 0.5062(3) 0.25533(7) 0.64343(5) 0.0174(2) Uani 1 1 d . . . . .
H13 H 0.386021 0.217174 0.614168 0.021 Uiso 1 1 calc R U . . .
C3 C 0.7179(3) 0.76760(7) 0.60334(5) 0.0166(2) Uani 1 1 d . . . . .
H3 H 0.640937 0.814032 0.629695 0.020 Uiso 1 1 calc R U . . .
C2 C 0.8713(3) 0.78781(6) 0.54639(4) 0.0158(2) Uani 1 1 d . . . . .
C8 C 0.8088(3) 0.49300(7) 0.65297(5) 0.0168(2) Uani 1 1 d . . . . .
H8 H 0.909378 0.532467 0.683616 0.020 Uiso 1 1 calc R U . . .
C1 C 0.9228(3) 0.88026(7) 0.52591(5) 0.0182(2) Uani 1 1 d . . . . .
C15 C 0.4344(3) 0.07623(7) 0.67719(5) 0.0239(2) Uani 1 1 d . . . . .
H15A H 0.556335 0.078087 0.637481 0.036 Uiso 1 1 calc R U . . .
H15B H 0.188923 0.092983 0.669272 0.036 Uiso 1 1 calc R U . . .
H15C H 0.446713 0.016038 0.694621 0.036 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 C12 1.3692(12) . ?
O3 C15 1.4314(13) . ?
O1 H1 0.8400 . ?
O1 C1 1.3105(12) . ?
O2 C1 1.2396(12) . ?
N1 C5 1.4076(13) . ?
N1 C8 1.2773(14) . ?
C5 C6 1.4021(14) . ?
C5 C4 1.4012(14) . ?
C12 C11 1.3944(14) . ?
C12 C13 1.3978(14) . ?
C10 H10 0.9500 . ?
C10 C11 1.3845(14) . ?
C10 C9 1.4015(14) . ?
C11 H11 0.9500 . ?
C7 H7 0.9500 . ?
C7 C6 1.3831(14) . ?
C7 C2 1.3976(14) . ?
C6 H6 0.9500 . ?
C4 H4 0.9500 . ?
C4 C3 1.3878(14) . ?
C9 C14 1.3973(14) . ?
C9 C8 1.4656(14) . ?
C14 H14 0.9500 . ?
C14 C13 1.3855(14) . ?
C13 H13 0.9500 . ?
C3 H3 0.9500 . ?
C3 C2 1.3983(14) . ?
C2 C1 1.4751(14) . ?
C8 H8 0.9500 . ?
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
C12 O3 C15 117.12(8) . . ?
C1 O1 H1 109.5 . . ?
C8 N1 C5 119.80(9) . . ?
C6 C5 N1 117.98(9) . . ?
C4 C5 N1 122.12(9) . . ?
C4 C5 C6 119.77(9) . . ?
O3 C12 C11 115.56(9) . . ?
O3 C12 C13 124.14(9) . . ?
C11 C12 C13 120.29(9) . . ?
C11 C10 H10 119.7 . . ?
C11 C10 C9 120.63(9) . . ?
C9 C10 H10 119.7 . . ?
C12 C11 H11 120.0 . . ?
C10 C11 C12 119.97(9) . . ?
C10 C11 H11 120.0 . . ?
C6 C7 H7 119.7 . . ?
C6 C7 C2 120.57(9) . . ?
C2 C7 H7 119.7 . . ?
C5 C6 H6 120.1 . . ?
C7 C6 C5 119.81(9) . . ?
C7 C6 H6 120.1 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 C5 120.09(9) . . ?
C3 C4 H4 120.0 . . ?
C10 C9 C8 120.78(9) . . ?
C14 C9 C10 118.50(9) . . ?
C14 C9 C8 120.70(9) . . ?
C9 C14 H14 119.2 . . ?
C13 C14 C9 121.54(9) . . ?
C13 C14 H14 119.2 . . ?
C12 C13 H13 120.5 . . ?
C14 C13 C12 119.05(9) . . ?
C14 C13 H13 120.5 . . ?
C4 C3 H3 120.0 . . ?
C4 C3 C2 120.09(9) . . ?
C2 C3 H3 120.0 . . ?
C7 C2 C3 119.66(9) . . ?
C7 C2 C1 118.60(9) . . ?
C3 C2 C1 121.74(9) . . ?
N1 C8 C9 121.23(9) . . ?
N1 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
O1 C1 C2 115.59(9) . . ?
O2 C1 O1 122.83(9) . . ?
O2 C1 C2 121.57(9) . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 C12 C11 C10 178.44(9) . . . . ?
O3 C12 C13 C14 -178.78(9) . . . . ?
N1 C5 C6 C7 177.24(9) . . . . ?
N1 C5 C4 C3 -176.33(9) . . . . ?
C5 N1 C8 C9 176.62(9) . . . . ?
C5 C4 C3 C2 -0.28(15) . . . . ?
C10 C9 C14 C13 -1.47(15) . . . . ?
C10 C9 C8 N1 172.32(10) . . . . ?
C11 C12 C13 C14 0.94(15) . . . . ?
C11 C10 C9 C14 1.10(15) . . . . ?
C11 C10 C9 C8 -177.45(9) . . . . ?
C7 C2 C1 O1 -176.39(9) . . . . ?
C7 C2 C1 O2 3.19(15) . . . . ?
C6 C5 C4 C3 -0.51(15) . . . . ?
C6 C7 C2 C3 0.41(15) . . . . ?
C6 C7 C2 C1 179.92(9) . . . . ?
C4 C5 C6 C7 1.25(15) . . . . ?
C4 C3 C2 C7 0.33(15) . . . . ?
C4 C3 C2 C1 -179.16(9) . . . . ?
C9 C10 C11 C12 0.26(15) . . . . ?
C9 C14 C13 C12 0.46(15) . . . . ?
C14 C9 C8 N1 -6.21(15) . . . . ?
C13 C12 C11 C10 -1.29(15) . . . . ?
C3 C2 C1 O1 3.12(15) . . . . ?
C3 C2 C1 O2 -177.31(10) . . . . ?
C2 C7 C6 C5 -1.20(15) . . . . ?
C8 N1 C5 C6 137.55(10) . . . . ?
C8 N1 C5 C4 -46.56(14) . . . . ?
C8 C9 C14 C13 177.08(9) . . . . ?
C15 O3 C12 C11 -177.57(9) . . . . ?
C15 O3 C12 C13 2.16(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 1.452
_oxdiff_exptl_absorpt_empirical_full_min 0.703
