# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
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data_bm_vial5_uo2
_database_code_depnum_ccdc_archive 'CCDC 2409152'
loop_
_audit_author_name
_audit_author_address
'Mark D. Smith'
;University of South Carolina
United States of America
;
_audit_update_record             
;
2024-12-10 deposited with the CCDC.	2025-06-13 downloaded from the CCDC.
;
_audit_creation_date             2024-06-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H20 N4 O12 U'
_chemical_formula_sum            'C19 H20 N4 O12 U'
_chemical_formula_weight         734.42
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
U U -9.6767 9.6646 '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                   10.8763(4)
_cell_length_b                   10.8816(4)
_cell_length_c                   11.2207(4)
_cell_angle_alpha                106.7650(10)
_cell_angle_beta                 113.8720(10)
_cell_angle_gamma                92.5920(10)
_cell_volume                     1142.70(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9624
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.066
_cell_measurement_theta_min      2.224
_shelx_estimated_absorpt_T_max   0.762
_shelx_estimated_absorpt_T_min   0.480
_exptl_absorpt_coefficient_mu    7.176
_exptl_absorpt_correction_T_max  0.2617
_exptl_absorpt_correction_T_min  0.1965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1341 before and 0.0654 after correction.
The Ratio of minimum to maximum transmission is 0.7509.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    2.134
_exptl_crystal_description       plate
_exptl_crystal_F_000             700
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_diffrn_reflns_av_R_equivalents  0.0601
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            44146
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.539
_diffrn_reflns_theta_min         1.989
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 PHOTON-II
_diffrn_detector_area_resol_mean 7.39
_diffrn_detector_type            'area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4914
_reflns_number_total             5262
_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       'SAINT V8.40B (Bruker, 2016)'
_computing_data_collection       'Bruker APEX3 v2019.1-0 (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2016)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  'OLEX2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         1.399
_refine_diff_density_min         -2.132
_refine_diff_density_rms         0.208
_refine_ls_extinction_coef       0.0016(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.313
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         5262
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0332
_refine_ls_restrained_S_all      1.313
_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)+(0.0442P)²+2.9994P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0944
_refine_ls_wR_factor_ref         0.0952
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O6-H6B \\sim O6-H6A
 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C12(H12), C13(H13), C16(H16), C17(H17),
 C19(H19)
3.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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
U1 U 0.09767(2) 0.33786(2) 0.65786(2) 0.01750(9) Uani 1 1 d . . . . .
O1 O 0.2669(4) 0.3355(4) 0.5877(4) 0.0211(8) Uani 1 1 d . . . . .
O2 O 0.3976(5) 0.4816(4) 0.1516(5) 0.0342(10) Uani 1 1 d . . . . .
O3 O 0.5503(5) 0.3637(5) 0.2117(5) 0.0366(11) Uani 1 1 d . . . . .
O4 O 0.1101(4) 0.1767(4) 0.6614(5) 0.0245(8) Uani 1 1 d . . . . .
O5 O 0.0819(4) 0.4977(4) 0.6560(4) 0.0235(8) Uani 1 1 d . . . . .
O6 O 0.3283(4) 0.4263(5) 0.8591(5) 0.0294(10) Uani 1 1 d D . . . .
H6A H 0.383(6) 0.477(6) 0.853(7) 0.030(19) Uiso 1 1 d D . . . .
H6B H 0.339(7) 0.446(6) 0.940(5) 0.018(16) Uiso 1 1 d D . . . .
O7 O 0.0035(4) 0.2456(4) 0.4002(4) 0.0248(8) Uani 1 1 d . . . . .
O8 O -0.1476(4) 0.2607(4) 0.4798(4) 0.0252(8) Uani 1 1 d . . . . .
O9 O -0.2139(5) 0.1835(5) 0.2562(5) 0.0380(11) Uani 1 1 d . . . . .
O10 O -0.0900(4) 0.3338(4) 0.7324(4) 0.0238(8) Uani 1 1 d . . . . .
O11 O 0.1125(4) 0.3890(4) 0.8982(4) 0.0282(9) Uani 1 1 d . . . . .
O12 O -0.0634(5) 0.3636(5) 0.9428(5) 0.0361(11) Uani 1 1 d . . . . .
N1 N 0.7504(5) 0.0393(4) 0.7039(5) 0.0188(9) Uani 1 1 d . . . . .
N2 N 0.4539(5) 0.4118(5) 0.2201(5) 0.0252(10) Uani 1 1 d . . . . .
N3 N -0.1237(5) 0.2274(5) 0.3726(5) 0.0229(10) Uani 1 1 d . . . . .
N4 N -0.0155(5) 0.3627(5) 0.8618(5) 0.0258(10) Uani 1 1 d . . . . .
C1 C 0.6549(6) 0.1105(5) 0.7028(6) 0.0185(10) Uani 1 1 d . . . . .
C2 C 0.6093(5) 0.1021(5) 0.8130(6) 0.0184(10) Uani 1 1 d . . . . .
C3 C 0.6997(6) 0.0129(5) 0.8730(6) 0.0224(11) Uani 1 1 d . . . . .
C4 C 0.7803(6) -0.0235(5) 0.8051(5) 0.0185(10) Uani 1 1 d . . . . .
C5 C 0.8705(6) -0.1079(5) 0.8327(6) 0.0226(11) Uani 1 1 d . . . . .
H5 H 0.925414 -0.130030 0.784698 0.027 Uiso 1 1 calc R U . . .
C6 C 0.8765(7) -0.1586(6) 0.9350(6) 0.0298(13) Uani 1 1 d . . . . .
H6 H 0.935624 -0.218691 0.956389 0.036 Uiso 1 1 calc R U . . .
C7 C 0.7983(7) -0.1236(6) 1.0062(6) 0.0316(14) Uani 1 1 d . . . . .
H7 H 0.806331 -0.158724 1.076783 0.038 Uiso 1 1 calc R U . . .
C8 C 0.7081(7) -0.0380(6) 0.9769(7) 0.0327(14) Uani 1 1 d . . . . .
H8 H 0.654015 -0.014781 1.025689 0.039 Uiso 1 1 calc R U . . .
C9 C 0.8209(5) 0.0169(5) 0.6143(6) 0.0203(11) Uani 1 1 d . . . . .
H9A H 0.795715 0.073198 0.557206 0.030 Uiso 1 1 calc R U . . .
H9B H 0.793965 -0.074800 0.554262 0.030 Uiso 1 1 calc R U . . .
H9C H 0.920068 0.037224 0.671513 0.030 Uiso 1 1 calc R U . . .
C10 C 0.4571(6) 0.0357(6) 0.7510(6) 0.0269(12) Uani 1 1 d . . . . .
H10A H 0.437872 -0.043780 0.672694 0.040 Uiso 1 1 calc R U . . .
H10B H 0.397772 0.095949 0.719243 0.040 Uiso 1 1 calc R U . . .
H10C H 0.439839 0.013093 0.821978 0.040 Uiso 1 1 calc R U . . .
C11 C 0.6389(7) 0.2365(6) 0.9244(6) 0.0273(12) Uani 1 1 d . . . . .
H11A H 0.580133 0.292964 0.883139 0.041 Uiso 1 1 calc R U . . .
H11B H 0.735074 0.276747 0.961471 0.041 Uiso 1 1 calc R U . . .
H11C H 0.620260 0.225186 0.999449 0.041 Uiso 1 1 calc R U . . .
C12 C 0.6044(6) 0.1804(5) 0.6077(6) 0.0197(10) Uani 1 1 d . . . . .
H12 H 0.649915 0.186513 0.552458 0.024 Uiso 1 1 calc R U . . .
C13 C 0.4945(5) 0.2379(5) 0.5937(5) 0.0179(10) Uani 1 1 d . . . . .
H13 H 0.456073 0.234849 0.655510 0.022 Uiso 1 1 calc R U . . .
C14 C 0.4275(6) 0.3040(5) 0.4956(5) 0.0184(10) Uani 1 1 d . . . . .
C15 C 0.3093(5) 0.3546(5) 0.5011(6) 0.0187(10) Uani 1 1 d . . . . .
C16 C 0.2430(6) 0.4239(5) 0.4105(6) 0.0219(11) Uani 1 1 d . . . . .
H16 H 0.165242 0.458579 0.413408 0.026 Uiso 1 1 calc R U . . .
C17 C 0.2897(6) 0.4412(5) 0.3199(6) 0.0239(11) Uani 1 1 d . . . . .
H17 H 0.245123 0.488077 0.260041 0.029 Uiso 1 1 calc R U . . .
C18 C 0.4035(6) 0.3896(5) 0.3153(5) 0.0191(10) Uani 1 1 d . . . . .
C19 C 0.4748(5) 0.3235(5) 0.4027(5) 0.0179(10) Uani 1 1 d . . . . .
H19 H 0.553878 0.292231 0.399399 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
U1 O1 2.275(4) . ?
U1 O4 1.775(4) . ?
U1 O5 1.761(4) . ?
U1 O6 2.502(4) . ?
U1 O7 2.501(4) . ?
U1 O8 2.516(4) . ?
U1 O10 2.503(4) . ?
U1 O11 2.526(4) . ?
O1 C15 1.292(6) . ?
O2 N2 1.242(6) . ?
O3 N2 1.218(7) . ?
O6 H6A 0.83(5) . ?
O6 H6B 0.83(5) . ?
O7 N3 1.281(6) . ?
O8 N3 1.287(6) . ?
O9 N3 1.207(7) . ?
O10 N4 1.275(7) . ?
O11 N4 1.274(6) . ?
O12 N4 1.215(7) . ?
N1 C1 1.322(7) . ?
N1 C4 1.425(7) . ?
N1 C9 1.469(7) . ?
N2 C18 1.453(7) . ?
C1 C2 1.531(7) . ?
C1 C12 1.432(8) . ?
C2 C3 1.513(8) . ?
C2 C10 1.554(8) . ?
C2 C11 1.543(8) . ?
C3 C4 1.380(8) . ?
C3 C8 1.402(8) . ?
C4 C5 1.379(8) . ?
C5 H5 0.9500 . ?
C5 C6 1.391(8) . ?
C6 H6 0.9500 . ?
C6 C7 1.382(10) . ?
C7 H7 0.9500 . ?
C7 C8 1.392(9) . ?
C8 H8 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12 0.9500 . ?
C12 C13 1.348(7) . ?
C13 H13 0.9500 . ?
C13 C14 1.455(7) . ?
C14 C15 1.438(7) . ?
C14 C19 1.396(7) . ?
C15 C16 1.422(8) . ?
C16 H16 0.9500 . ?
C16 C17 1.359(8) . ?
C17 H17 0.9500 . ?
C17 C18 1.396(8) . ?
C18 C19 1.386(8) . ?
C19 H19 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
O1 U1 O6 68.45(14) . . ?
O1 U1 O7 68.57(14) . . ?
O1 U1 O8 119.49(14) . . ?
O1 U1 O10 178.43(13) . . ?
O1 U1 O11 130.04(14) . . ?
O4 U1 O1 89.63(16) . . ?
O4 U1 O6 91.27(18) . . ?
O4 U1 O7 87.98(17) . . ?
O4 U1 O8 90.31(17) . . ?
O4 U1 O10 88.93(16) . . ?
O4 U1 O11 85.29(17) . . ?
O5 U1 O1 91.92(17) . . ?
O5 U1 O4 178.45(16) . . ?
O5 U1 O6 89.24(18) . . ?
O5 U1 O7 92.65(17) . . ?
O5 U1 O8 88.98(17) . . ?
O5 U1 O10 89.52(16) . . ?
O5 U1 O11 93.66(17) . . ?
O6 U1 O8 171.92(13) . . ?
O6 U1 O10 112.21(13) . . ?
O6 U1 O11 62.03(13) . . ?
O7 U1 O6 137.02(13) . . ?
O7 U1 O8 50.96(13) . . ?
O7 U1 O10 110.74(13) . . ?
O7 U1 O11 160.03(14) . . ?
O8 U1 O11 110.23(13) . . ?
O10 U1 O8 59.89(13) . . ?
O10 U1 O11 50.45(13) . . ?
C15 O1 U1 148.3(4) . . ?
U1 O6 H6A 118(5) . . ?
U1 O6 H6B 122(5) . . ?
H6A O6 H6B 110(7) . . ?
N3 O7 U1 97.8(3) . . ?
N3 O8 U1 96.9(3) . . ?
N4 O10 U1 98.0(3) . . ?
N4 O11 U1 96.9(3) . . ?
C1 N1 C4 111.9(4) . . ?
C1 N1 C9 128.4(4) . . ?
C4 N1 C9 119.7(4) . . ?
O2 N2 C18 118.1(5) . . ?
O3 N2 O2 122.4(5) . . ?
O3 N2 C18 119.4(5) . . ?
O7 N3 O8 114.3(4) . . ?
O9 N3 O7 123.2(5) . . ?
O9 N3 O8 122.5(5) . . ?
O11 N4 O10 114.4(5) . . ?
O12 N4 O10 122.3(5) . . ?
O12 N4 O11 123.2(5) . . ?
N1 C1 C2 109.7(4) . . ?
N1 C1 C12 122.6(5) . . ?
C12 C1 C2 127.7(5) . . ?
C1 C2 C10 113.1(5) . . ?
C1 C2 C11 112.1(4) . . ?
C3 C2 C1 100.5(4) . . ?
C3 C2 C10 108.9(4) . . ?
C3 C2 C11 110.9(5) . . ?
C11 C2 C10 110.9(4) . . ?
C4 C3 C2 110.1(5) . . ?
C4 C3 C8 119.1(5) . . ?
C8 C3 C2 130.8(5) . . ?
C3 C4 N1 107.8(5) . . ?
C5 C4 N1 128.0(5) . . ?
C5 C4 C3 124.1(5) . . ?
C4 C5 H5 122.0 . . ?
C4 C5 C6 116.0(5) . . ?
C6 C5 H5 122.0 . . ?
C5 C6 H6 119.2 . . ?
C7 C6 C5 121.5(6) . . ?
C7 C6 H6 119.2 . . ?
C6 C7 H7 119.2 . . ?
C6 C7 C8 121.5(6) . . ?
C8 C7 H7 119.2 . . ?
C3 C8 H8 121.1 . . ?
C7 C8 C3 117.7(6) . . ?
C7 C8 H8 121.1 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C2 C10 H10A 109.5 . . ?
C2 C10 H10B 109.5 . . ?
C2 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C2 C11 H11A 109.5 . . ?
C2 C11 H11B 109.5 . . ?
C2 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C1 C12 H12 118.8 . . ?
C13 C12 C1 122.3(5) . . ?
C13 C12 H12 118.8 . . ?
C12 C13 H13 116.0 . . ?
C12 C13 C14 127.9(5) . . ?
C14 C13 H13 116.0 . . ?
C15 C14 C13 116.4(5) . . ?
C19 C14 C13 123.5(5) . . ?
C19 C14 C15 120.0(5) . . ?
O1 C15 C14 119.1(5) . . ?
O1 C15 C16 122.3(5) . . ?
C16 C15 C14 118.6(5) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 C15 120.7(5) . . ?
C17 C16 H16 119.6 . . ?
C16 C17 H17 120.2 . . ?
C16 C17 C18 119.5(5) . . ?
C18 C17 H17 120.2 . . ?
C17 C18 N2 118.7(5) . . ?
C19 C18 N2 118.5(5) . . ?
C19 C18 C17 122.7(5) . . ?
C14 C19 H19 120.8 . . ?
C18 C19 C14 118.4(5) . . ?
C18 C19 H19 120.8 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O6 H6A O2 0.83(5) 2.43(6) 3.161(6) 147(6) 2_666 yes
O6 H6A O3 0.83(5) 2.26(5) 3.037(6) 157(7) 2_666 yes
O6 H6B O2 0.83(5) 2.10(5) 2.918(6) 170(6) 1_556 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
U1 O1 C15 C14 -165.5(5) . . . . ?
U1 O1 C15 C16 14.5(10) . . . . ?
U1 O7 N3 O8 -0.3(5) . . . . ?
U1 O7 N3 O9 179.3(5) . . . . ?
U1 O8 N3 O7 0.3(5) . . . . ?
U1 O8 N3 O9 -179.3(5) . . . . ?
U1 O10 N4 O11 4.6(5) . . . . ?
U1 O10 N4 O12 -174.8(5) . . . . ?
U1 O11 N4 O10 -4.6(5) . . . . ?
U1 O11 N4 O12 174.9(5) . . . . ?
O1 C15 C16 C17 -179.4(5) . . . . ?
O2 N2 C18 C17 3.6(7) . . . . ?
O2 N2 C18 C19 -173.2(5) . . . . ?
O3 N2 C18 C17 -177.6(5) . . . . ?
O3 N2 C18 C19 5.6(8) . . . . ?
N1 C1 C2 C3 0.2(5) . . . . ?
N1 C1 C2 C10 -115.7(5) . . . . ?
N1 C1 C2 C11 118.0(5) . . . . ?
N1 C1 C12 C13 170.6(5) . . . . ?
N1 C4 C5 C6 -178.0(5) . . . . ?
N2 C18 C19 C14 179.0(5) . . . . ?
C1 N1 C4 C3 -1.1(6) . . . . ?
C1 N1 C4 C5 177.9(5) . . . . ?
C1 C2 C3 C4 -0.8(6) . . . . ?
C1 C2 C3 C8 -178.2(6) . . . . ?
C1 C12 C13 C14 -175.6(5) . . . . ?
C2 C1 C12 C13 -8.0(9) . . . . ?
C2 C3 C4 N1 1.2(6) . . . . ?
C2 C3 C4 C5 -177.8(5) . . . . ?
C2 C3 C8 C7 177.1(6) . . . . ?
C3 C4 C5 C6 0.8(8) . . . . ?
C4 N1 C1 C2 0.5(6) . . . . ?
C4 N1 C1 C12 -178.3(5) . . . . ?
C4 C3 C8 C7 -0.1(9) . . . . ?
C4 C5 C6 C7 -1.4(9) . . . . ?
C5 C6 C7 C8 1.3(10) . . . . ?
C6 C7 C8 C3 -0.5(10) . . . . ?
C8 C3 C4 N1 178.9(5) . . . . ?
C8 C3 C4 C5 -0.1(9) . . . . ?
C9 N1 C1 C2 178.6(5) . . . . ?
C9 N1 C1 C12 -0.2(8) . . . . ?
C9 N1 C4 C3 -179.3(5) . . . . ?
C9 N1 C4 C5 -0.4(8) . . . . ?
C10 C2 C3 C4 118.1(5) . . . . ?
C10 C2 C3 C8 -59.2(8) . . . . ?
C11 C2 C3 C4 -119.5(5) . . . . ?
C11 C2 C3 C8 63.1(8) . . . . ?
C12 C1 C2 C3 178.9(5) . . . . ?
C12 C1 C2 C10 63.0(7) . . . . ?
C12 C1 C2 C11 -63.3(7) . . . . ?
C12 C13 C14 C15 178.7(5) . . . . ?
C12 C13 C14 C19 -3.5(9) . . . . ?
C13 C14 C15 O1 -2.2(7) . . . . ?
C13 C14 C15 C16 177.9(5) . . . . ?
C13 C14 C19 C18 -179.1(5) . . . . ?
C14 C15 C16 C17 0.5(8) . . . . ?
C15 C14 C19 C18 -1.4(7) . . . . ?
C15 C16 C17 C18 0.3(8) . . . . ?
C16 C17 C18 N2 -178.5(5) . . . . ?
C16 C17 C18 C19 -1.8(8) . . . . ?
C17 C18 C19 C14 2.3(8) . . . . ?
C19 C14 C15 O1 179.9(5) . . . . ?
C19 C14 C15 C16 0.0(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_u_csp
_database_code_depnum_ccdc_archive 'CCDC 2454510'
loop_
_audit_author_name
_audit_author_address
'Mark D. Smith'
;University of South Carolina
United States of America
;
_audit_update_record             
;
2025-05-27 deposited with the CCDC.	2025-06-13 downloaded from the CCDC.
;
_audit_creation_date             2022-09-23
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl, C20 H19 N2 O5'
_chemical_formula_sum            'C20 H19 Cl N2 O5'
_chemical_formula_weight         402.82
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   6.8431(3)
_cell_length_b                   21.1213(9)
_cell_length_c                   26.1977(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3786.5(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9967
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.520
_cell_measurement_theta_min      2.478
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.950
_exptl_absorpt_coefficient_mu    0.237
_exptl_absorpt_correction_T_max  0.5629
_exptl_absorpt_correction_T_min  0.5311
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1211 before and 0.0639 after correction.
The Ratio of minimum to maximum transmission is 0.9435.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_description       needle
_exptl_crystal_F_000             1680
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_diffrn_reflns_av_R_equivalents  0.0701
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            53020
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.535
_diffrn_reflns_theta_min         1.928
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 PHOTON-II
_diffrn_detector_area_resol_mean 7.39
_diffrn_detector_type            'area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3555
_reflns_number_total             4354
_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       'SAINT V8.40B (Bruker, 2016)'
_computing_data_collection       'Bruker APEX3 v2019.1-0 (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2016)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  'OLEX2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4354
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0710
_refine_ls_R_factor_gt           0.0532
_refine_ls_restrained_S_all      1.095
_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)+(0.0347P)²+5.0191P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1060
_refine_ls_wR_factor_ref         0.1131
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C8(H8), C13(H13), C14(H14), C17(H17), C18(H18), C20(H20)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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 0.37174(8) 0.72123(2) 0.08700(2) 0.02011(14) Uani 1 1 d . . . . .
O1 O 0.1881(3) 0.40934(8) 0.54390(6) 0.0248(4) Uani 1 1 d . . . . .
H1 H 0.161(4) 0.3684(14) 0.5502(11) 0.038(8) Uiso 1 1 d . . . . .
O2 O 0.2078(3) 0.37756(7) 0.46219(6) 0.0300(4) Uani 1 1 d . . . . .
O3 O 0.3928(2) 0.71724(7) 0.19933(6) 0.0187(3) Uani 1 1 d . . . . .
H3 H 0.388(4) 0.7196(13) 0.1659(11) 0.035(8) Uiso 1 1 d . . . . .
O4 O 0.6886(3) 0.98720(7) 0.25794(7) 0.0288(4) Uani 1 1 d . . . . .
O5 O 0.6186(3) 0.94956(8) 0.33265(6) 0.0290(4) Uani 1 1 d . . . . .
N1 N 0.3534(3) 0.67041(8) 0.43432(6) 0.0137(4) Uani 1 1 d . . . . .
N2 N 0.6277(3) 0.94489(8) 0.28586(7) 0.0205(4) Uani 1 1 d . . . . .
C1 C 0.3655(3) 0.66645(9) 0.38419(7) 0.0134(4) Uani 1 1 d . . . . .
C2 C 0.3407(3) 0.59786(9) 0.36706(7) 0.0147(4) Uani 1 1 d . . . . .
C3 C 0.3079(3) 0.56569(10) 0.41809(8) 0.0143(4) Uani 1 1 d . . . . .
C4 C 0.3169(3) 0.61057(10) 0.45673(8) 0.0140(4) Uani 1 1 d . . . . .
C5 C 0.2911(3) 0.59626(10) 0.50799(8) 0.0166(4) Uani 1 1 d . . . . .
H5 H 0.297444 0.627896 0.533715 0.020 Uiso 1 1 calc R U . . .
C6 C 0.2555(3) 0.53324(10) 0.51963(8) 0.0180(4) Uani 1 1 d . . . . .
H6 H 0.236615 0.521226 0.554223 0.022 Uiso 1 1 calc R U . . .
C7 C 0.2468(3) 0.48711(10) 0.48154(8) 0.0176(4) Uani 1 1 d . . . . .
C8 C 0.2727(3) 0.50340(10) 0.42999(8) 0.0164(4) Uani 1 1 d . . . . .
H8 H 0.265997 0.472106 0.404009 0.020 Uiso 1 1 calc R U . . .
C9 C 0.2120(3) 0.41893(10) 0.49389(8) 0.0199(5) Uani 1 1 d . . . . .
C10 C 0.3713(4) 0.72896(10) 0.46417(8) 0.0204(5) Uani 1 1 d . . . . .
H10A H 0.493246 0.750528 0.455070 0.031 Uiso 1 1 calc R U . . .
H10B H 0.372503 0.718669 0.500645 0.031 Uiso 1 1 calc R U . . .
H10C H 0.260259 0.756745 0.456718 0.031 Uiso 1 1 calc R U . . .
C11 C 0.5290(3) 0.57316(10) 0.34176(8) 0.0190(5) Uani 1 1 d . . . . .
H11A H 0.547770 0.594374 0.308855 0.029 Uiso 1 1 calc R U . . .
H11B H 0.518167 0.527384 0.336329 0.029 Uiso 1 1 calc R U . . .
H11C H 0.640890 0.581996 0.363995 0.029 Uiso 1 1 calc R U . . .
C12 C 0.1603(3) 0.58907(10) 0.33258(8) 0.0196(5) Uani 1 1 d . . . . .
H12A H 0.044781 0.606443 0.349671 0.029 Uiso 1 1 calc R U . . .
H12B H 0.140328 0.543867 0.325935 0.029 Uiso 1 1 calc R U . . .
H12C H 0.181138 0.611298 0.300197 0.029 Uiso 1 1 calc R U . . .
C13 C 0.3993(3) 0.72180(10) 0.35405(8) 0.0153(4) Uani 1 1 d . . . . .
H13 H 0.409936 0.761151 0.371397 0.018 Uiso 1 1 calc R U . . .
C14 C 0.4172(3) 0.72220(10) 0.30294(8) 0.0154(4) Uani 1 1 d . . . . .
H14 H 0.399433 0.683169 0.285531 0.018 Uiso 1 1 calc R U . . .
C15 C 0.4615(3) 0.77765(10) 0.27227(8) 0.0155(4) Uani 1 1 d . . . . .
C16 C 0.4518(3) 0.77288(10) 0.21844(8) 0.0155(4) Uani 1 1 d . . . . .
C17 C 0.5005(3) 0.82491(10) 0.18752(8) 0.0180(4) Uani 1 1 d . . . . .
H17 H 0.493155 0.821383 0.151424 0.022 Uiso 1 1 calc R U . . .
C18 C 0.5588(3) 0.88090(10) 0.20950(8) 0.0186(4) Uani 1 1 d . . . . .
H18 H 0.594268 0.915952 0.188755 0.022 Uiso 1 1 calc R U . . .
C19 C 0.5653(3) 0.88569(10) 0.26230(8) 0.0176(4) Uani 1 1 d . . . . .
C20 C 0.5180(3) 0.83557(10) 0.29369(8) 0.0164(4) Uani 1 1 d . . . . .
H20 H 0.523626 0.840325 0.329722 0.020 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.90(3) . ?
O1 C9 1.336(3) . ?
O2 C9 1.206(3) . ?
O3 H3 0.88(3) . ?
O3 C16 1.340(3) . ?
O4 N2 1.228(2) . ?
O5 N2 1.231(2) . ?
N1 C1 1.319(2) . ?
N1 C4 1.416(3) . ?
N1 C10 1.468(3) . ?
N2 C19 1.458(3) . ?
C1 C2 1.526(3) . ?
C1 C13 1.430(3) . ?
C2 C3 1.516(3) . ?
C2 C11 1.540(3) . ?
C2 C12 1.541(3) . ?
C3 C4 1.388(3) . ?
C3 C8 1.373(3) . ?
C4 C5 1.388(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.387(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.396(3) . ?
C7 C8 1.405(3) . ?
C7 C9 1.495(3) . ?
C8 H8 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13 0.9500 . ?
C13 C14 1.345(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.452(3) . ?
C15 C16 1.415(3) . ?
C15 C20 1.400(3) . ?
C16 C17 1.405(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.374(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.388(3) . ?
C19 C20 1.379(3) . ?
C20 H20 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
C9 O1 H1 110.6(18) . . ?
C16 O3 H3 109.5(18) . . ?
C1 N1 C4 111.55(17) . . ?
C1 N1 C10 125.36(18) . . ?
C4 N1 C10 123.08(16) . . ?
O4 N2 O5 123.50(19) . . ?
O4 N2 C19 118.13(18) . . ?
O5 N2 C19 118.36(18) . . ?
N1 C1 C2 110.25(17) . . ?
N1 C1 C13 120.55(18) . . ?
C13 C1 C2 129.20(17) . . ?
C1 C2 C11 110.81(17) . . ?
C1 C2 C12 112.07(17) . . ?
C3 C2 C1 100.52(16) . . ?
C3 C2 C11 110.58(17) . . ?
C3 C2 C12 110.14(17) . . ?
C11 C2 C12 112.16(17) . . ?
C4 C3 C2 109.29(17) . . ?
C8 C3 C2 130.95(18) . . ?
C8 C3 C4 119.75(19) . . ?
C3 C4 N1 108.37(17) . . ?
C5 C4 N1 128.18(19) . . ?
C5 C4 C3 123.45(19) . . ?
C4 C5 H5 121.8 . . ?
C6 C5 C4 116.36(19) . . ?
C6 C5 H5 121.8 . . ?
C5 C6 H6 119.3 . . ?
C5 C6 C7 121.36(19) . . ?
C7 C6 H6 119.3 . . ?
C6 C7 C8 120.71(19) . . ?
C6 C7 C9 121.64(19) . . ?
C8 C7 C9 117.65(19) . . ?
C3 C8 C7 118.37(19) . . ?
C3 C8 H8 120.8 . . ?
C7 C8 H8 120.8 . . ?
O1 C9 C7 112.20(19) . . ?
O2 C9 O1 124.2(2) . . ?
O2 C9 C7 123.6(2) . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C2 C11 H11A 109.5 . . ?
C2 C11 H11B 109.5 . . ?
C2 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C2 C12 H12A 109.5 . . ?
C2 C12 H12B 109.5 . . ?
C2 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C1 C13 H13 117.6 . . ?
C14 C13 C1 124.74(19) . . ?
C14 C13 H13 117.6 . . ?
C13 C14 H14 117.4 . . ?
C13 C14 C15 125.11(19) . . ?
C15 C14 H14 117.4 . . ?
C16 C15 C14 118.95(19) . . ?
C20 C15 C14 122.71(18) . . ?
C20 C15 C16 118.32(19) . . ?
O3 C16 C15 116.67(19) . . ?
O3 C16 C17 122.83(19) . . ?
C17 C16 C15 120.49(19) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 C16 120.02(19) . . ?
C18 C17 H17 120.0 . . ?
C17 C18 H18 120.3 . . ?
C17 C18 C19 119.3(2) . . ?
C19 C18 H18 120.3 . . ?
C18 C19 N2 119.59(19) . . ?
C20 C19 N2 118.34(19) . . ?
C20 C19 C18 122.1(2) . . ?
C15 C20 H20 120.1 . . ?
C19 C20 C15 119.77(19) . . ?
C19 C20 H20 120.1 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 Cl1 0.90(3) 2.14(3) 3.0080(17) 163(3) 2_565 yes
O3 H3 Cl1 0.88(3) 2.07(3) 2.9474(16) 178(3) . yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 C16 C17 C18 179.6(2) . . . . ?
O4 N2 C19 C18 -6.1(3) . . . . ?
O4 N2 C19 C20 172.7(2) . . . . ?
O5 N2 C19 C18 174.7(2) . . . . ?
O5 N2 C19 C20 -6.5(3) . . . . ?
N1 C1 C2 C3 1.3(2) . . . . ?
N1 C1 C2 C11 -115.66(19) . . . . ?
N1 C1 C2 C12 118.2(2) . . . . ?
N1 C1 C13 C14 178.8(2) . . . . ?
N1 C4 C5 C6 179.5(2) . . . . ?
N2 C19 C20 C15 -178.64(19) . . . . ?
C1 N1 C4 C3 0.8(2) . . . . ?
C1 N1 C4 C5 -178.5(2) . . . . ?
C1 C2 C3 C4 -0.8(2) . . . . ?
C1 C2 C3 C8 178.9(2) . . . . ?
C1 C13 C14 C15 -176.7(2) . . . . ?
C2 C1 C13 C14 -0.6(4) . . . . ?
C2 C3 C4 N1 0.1(2) . . . . ?
C2 C3 C4 C5 179.4(2) . . . . ?
C2 C3 C8 C7 -179.7(2) . . . . ?
C3 C4 C5 C6 0.2(3) . . . . ?
C4 N1 C1 C2 -1.3(2) . . . . ?
C4 N1 C1 C13 179.21(18) . . . . ?
C4 C3 C8 C7 0.0(3) . . . . ?
C4 C5 C6 C7 0.1(3) . . . . ?
C5 C6 C7 C8 -0.4(3) . . . . ?
C5 C6 C7 C9 178.9(2) . . . . ?
C6 C7 C8 C3 0.4(3) . . . . ?
C6 C7 C9 O1 1.1(3) . . . . ?
C6 C7 C9 O2 -178.3(2) . . . . ?
C8 C3 C4 N1 -179.65(19) . . . . ?
C8 C3 C4 C5 -0.3(3) . . . . ?
C8 C7 C9 O1 -179.5(2) . . . . ?
C8 C7 C9 O2 1.1(3) . . . . ?
C9 C7 C8 C3 -179.0(2) . . . . ?
C10 N1 C1 C2 179.66(19) . . . . ?
C10 N1 C1 C13 0.2(3) . . . . ?
C10 N1 C4 C3 179.83(19) . . . . ?
C10 N1 C4 C5 0.5(3) . . . . ?
C11 C2 C3 C4 116.33(19) . . . . ?
C11 C2 C3 C8 -64.0(3) . . . . ?
C12 C2 C3 C4 -119.14(19) . . . . ?
C12 C2 C3 C8 60.5(3) . . . . ?
C13 C1 C2 C3 -179.3(2) . . . . ?
C13 C1 C2 C11 63.7(3) . . . . ?
C13 C1 C2 C12 -62.4(3) . . . . ?
C13 C14 C15 C16 -172.1(2) . . . . ?
C13 C14 C15 C20 9.3(3) . . . . ?
C14 C15 C16 O3 2.9(3) . . . . ?
C14 C15 C16 C17 -177.71(19) . . . . ?
C14 C15 C20 C19 177.5(2) . . . . ?
C15 C16 C17 C18 0.2(3) . . . . ?
C16 C15 C20 C19 -1.1(3) . . . . ?
C16 C17 C18 C19 -1.2(3) . . . . ?
C17 C18 C19 N2 179.8(2) . . . . ?
C17 C18 C19 C20 1.1(3) . . . . ?
C18 C19 C20 C15 0.1(3) . . . . ?
C20 C15 C16 O3 -178.47(19) . . . . ?
C20 C15 C16 C17 0.9(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
