# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_B22037_a
_database_code_depnum_ccdc_archive 'CCDC 2155745'
loop_
_audit_author_name
_audit_author_address
'Jeffery Bertke'
;Georgetown University
United States of America
;
_audit_update_record             
;
2022-03-01 deposited with the CCDC.	2023-12-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H18 Cl N O3, C2 H3 N'
_chemical_formula_sum            'C26 H21 Cl N2 O3'
_chemical_formula_weight         444.90

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.8943(5)
_cell_length_b                   13.4561(11)
_cell_length_c                   27.524(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2183.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9441
_cell_measurement_theta_min      2.69
_cell_measurement_theta_max      26.36
_exptl_crystal_description       column
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_F_000             928
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.426
_exptl_crystal_size_mid          0.088
_exptl_crystal_size_min          0.066
_exptl_absorpt_coefficient_mu    0.206
_shelx_estimated_absorpt_T_min   0.917
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.93581
_exptl_absorpt_correction_T_max  0.99249
_exptl_absorpt_process_details   'SADABS V2016/2 (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_measurement_device_type  'Bruker D8 Quest/Photon 100'
_diffrn_measurement_method       'profile data from φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            133401
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_av_R_equivalents  0.1071
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         2.117
_diffrn_reflns_theta_max         26.437
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4489
_reflns_number_gt                4167
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.722
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_fraction_full    1.000

_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.
;

_computing_data_collection       'APEX3 V2016.5-0 (Bruker, 2016)'
_computing_cell_refinement       'SAINT V8.37A (Bruker, 2005)'
_computing_data_reduction        
; 
SAINT V8.37A, XPREP v2014/2, SADABS V2016/2 (Bruker, 2016) 
;
_computing_structure_solution    'SHELX-2014-5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELX-2018-3 (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXLE v932 (Hubschle, 2011)'
_computing_publication_material  'XCIF V2014-2 (Bruker, 2014)'

_refine_special_details          
; 
Structure was phased by intrinsic methods (Sheldrick, 2015).  Systematic 
conditions suggested the ambiguous space group.  The space group choice was 
confirmed by successful convergence of the full-matrix least-squares 
refinement on F².  The final map had no significant features.  A final 
analysis of variance between observed and calculated structure factors showed 
little dependence on amplitude and resolution. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0282P)²+0.5917P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     intrinsic
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1681 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(2)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4489
_refine_ls_number_parameters     296
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0262
_refine_ls_wR_factor_ref         0.0617
_refine_ls_wR_factor_gt          0.0597
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.95159(8) 0.38248(3) 0.74703(2) 0.01576(11) Uani 1 1 d . . . . .
O1 O 0.6845(2) 0.19867(10) 0.74745(5) 0.0164(3) Uani 1 1 d . . . . .
O2 O 0.3946(2) 0.45627(10) 0.61240(5) 0.0202(3) Uani 1 1 d . . . . .
O3 O 1.0452(2) 0.66303(10) 0.67355(5) 0.0165(3) Uani 1 1 d . . . . .
H3 H 1.102(4) 0.6840(18) 0.6985(9) 0.025 Uiso 1 1 d . U . . .
N1 N 0.7589(3) 0.51148(12) 0.67032(6) 0.0151(4) Uani 1 1 d . . . . .
H1 H 0.884(4) 0.5195(18) 0.6853(9) 0.023 Uiso 1 1 d . U . . .
N2 N 0.5861(4) 0.21798(15) 0.54718(7) 0.0308(5) Uani 1 1 d . . . . .
C1 C 0.7206(3) 0.35556(14) 0.71023(7) 0.0123(4) Uani 1 1 d . . . . .
C2 C 0.6157(3) 0.25992(14) 0.71716(6) 0.0118(4) Uani 1 1 d . . . . .
C3 C 0.4107(3) 0.23687(14) 0.68781(6) 0.0124(4) Uani 1 1 d . . . . .
C4 C 0.2951(3) 0.14779(14) 0.69514(7) 0.0148(4) Uani 1 1 d . . . . .
H4 H 0.351510 0.100513 0.717750 0.018 Uiso 1 1 calc R U . . .
C5 C 0.0972(4) 0.12802(15) 0.66940(7) 0.0172(4) Uani 1 1 d . . . . .
H5 H 0.016416 0.068021 0.675050 0.021 Uiso 1 1 calc R U . . .
C6 C 0.0171(3) 0.19615(14) 0.63531(7) 0.0160(4) Uani 1 1 d . . . . .
H6 H -0.117706 0.182295 0.617634 0.019 Uiso 1 1 calc R U . . .
C7 C 0.1336(3) 0.28405(15) 0.62713(7) 0.0155(4) Uani 1 1 d . . . . .
H7 H 0.079917 0.329940 0.603556 0.019 Uiso 1 1 calc R U . . .
C8 C 0.3294(3) 0.30502(14) 0.65351(7) 0.0120(4) Uani 1 1 d . . . . .
C9 C 0.4498(3) 0.39988(14) 0.64493(6) 0.0132(4) Uani 1 1 d . . . . .
C10 C 0.6495(3) 0.42503(14) 0.67680(7) 0.0122(4) Uani 1 1 d . . . . .
C11 C 0.6868(3) 0.60329(13) 0.64528(6) 0.0126(4) Uani 1 1 d . . . . .
H11 H 0.519453 0.611606 0.649692 0.015 Uiso 1 1 calc R U . . .
C12 C 0.8104(3) 0.68803(14) 0.67301(7) 0.0136(4) Uani 1 1 d . . . . .
H12 H 0.754112 0.688736 0.707286 0.016 Uiso 1 1 calc R U . . .
C13 C 0.7634(3) 0.78899(14) 0.65056(6) 0.0123(4) Uani 1 1 d . . . . .
C14 C 0.9192(4) 0.83576(15) 0.62061(7) 0.0154(4) Uani 1 1 d . . . . .
H14 H 1.060714 0.804796 0.613954 0.019 Uiso 1 1 calc R U . . .
C15 C 0.8694(4) 0.92816(15) 0.60019(7) 0.0191(4) Uani 1 1 d . . . . .
H15 H 0.977766 0.959984 0.579924 0.023 Uiso 1 1 calc R U . . .
C16 C 0.6637(4) 0.97363(15) 0.60922(7) 0.0189(4) Uani 1 1 d . . . . .
H16 H 0.630164 1.036496 0.595243 0.023 Uiso 1 1 calc R U . . .
C17 C 0.5059(3) 0.92661(14) 0.63896(7) 0.0187(4) Uani 1 1 d . . . . .
H17 H 0.363717 0.957300 0.645194 0.022 Uiso 1 1 calc R U . . .
C18 C 0.5556(4) 0.83488(14) 0.65957(7) 0.0153(4) Uani 1 1 d . . . . .
H18 H 0.447319 0.803262 0.679929 0.018 Uiso 1 1 calc R U . . .
C19 C 0.7400(3) 0.60466(14) 0.59112(7) 0.0127(4) Uani 1 1 d . . . . .
C20 C 0.5858(4) 0.64830(14) 0.55962(7) 0.0149(4) Uani 1 1 d . . . . .
H20 H 0.445852 0.672884 0.571810 0.018 Uiso 1 1 calc R U . . .
C21 C 0.6345(4) 0.65639(15) 0.51025(7) 0.0179(4) Uani 1 1 d . . . . .
H21 H 0.528053 0.686355 0.488877 0.021 Uiso 1 1 calc R U . . .
C22 C 0.8391(4) 0.62055(15) 0.49235(7) 0.0191(4) Uani 1 1 d . . . . .
H22 H 0.873177 0.626222 0.458727 0.023 Uiso 1 1 calc R U . . .
C23 C 0.9928(3) 0.57665(15) 0.52356(7) 0.0196(5) Uani 1 1 d . . . . .
H23 H 1.132245 0.551802 0.511259 0.023 Uiso 1 1 calc R U . . .
C24 C 0.9446(4) 0.56855(14) 0.57302(7) 0.0166(4) Uani 1 1 d . . . . .
H24 H 1.051170 0.538436 0.594316 0.020 Uiso 1 1 calc R U . . .
C25 C 0.5785(4) 0.29198(16) 0.52708(7) 0.0216(4) Uani 1 1 d . . . . .
C26 C 0.5680(4) 0.38687(15) 0.50134(8) 0.0257(5) Uani 1 1 d . . . . .
H26A H 0.689597 0.389700 0.477086 0.039 Uiso 1 1 calc R U . . .
H26B H 0.586728 0.441433 0.524581 0.039 Uiso 1 1 calc R U . . .
H26C H 0.420787 0.393113 0.485086 0.039 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.
;

_exptl_special_details           
; 
One distinct cell was identified using APEX3 (Bruker, 2016).  Eight frame 
series were integrated and filtered for statistical outliers using SAINT 
(Bruker, 2016) then corrected for absorption by integration using 
SAINT/SADABS v2014/2 (Bruker, 2016) to sort, merge, and scale the combined 
data.  No decay correction was applied.    
;

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1.00 0.00 0.00 0.2130
1.00 0.00 0.00 0.2020
0.00 -1.00 0.00 0.0330
0.00 0.00 1.00 0.0440
0.00 0.00 -1.00 0.0180
0.00 1.00 1.00 0.0110

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
Cl1 C1 1.7353(19) . ?
O1 C2 1.241(2) . ?
O2 C9 1.218(2) . ?
O3 C12 1.424(2) . ?
O3 H3 0.82(3) . ?
N1 C10 1.342(3) . ?
N1 C11 1.477(2) . ?
N1 H1 0.85(3) . ?
N2 C25 1.140(3) . ?
C1 C10 1.377(3) . ?
C1 C2 1.441(3) . ?
C2 C3 1.486(3) . ?
C3 C4 1.394(3) . ?
C3 C8 1.401(3) . ?
C4 C5 1.391(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.394(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.386(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.392(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.479(3) . ?
C9 C10 1.507(3) . ?
C11 C19 1.524(2) . ?
C11 C12 1.554(3) . ?
C11 H11 1.0000 . ?
C12 C13 1.518(3) . ?
C12 H12 1.0000 . ?
C13 C14 1.385(3) . ?
C13 C18 1.394(3) . ?
C14 C15 1.396(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.381(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.391(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.390(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.387(3) . ?
C19 C24 1.392(3) . ?
C20 C21 1.393(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.389(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.381(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.395(3) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 C26 1.462(3) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 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 H3 109.2(18) . . ?
C10 N1 C11 130.47(17) . . ?
C10 N1 H1 117.5(16) . . ?
C11 N1 H1 111.6(16) . . ?
C10 C1 C2 124.37(17) . . ?
C10 C1 Cl1 119.15(14) . . ?
C2 C1 Cl1 116.49(14) . . ?
O1 C2 C1 122.84(18) . . ?
O1 C2 C3 119.50(17) . . ?
C1 C2 C3 117.61(16) . . ?
C4 C3 C8 119.55(18) . . ?
C4 C3 C2 119.90(17) . . ?
C8 C3 C2 120.53(17) . . ?
C5 C4 C3 120.08(18) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 120.08(18) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C7 C6 C5 120.17(18) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C8 119.94(18) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C7 C8 C3 120.16(18) . . ?
C7 C8 C9 119.29(17) . . ?
C3 C8 C9 120.55(17) . . ?
O2 C9 C8 121.79(18) . . ?
O2 C9 C10 119.79(17) . . ?
C8 C9 C10 118.40(15) . . ?
N1 C10 C1 122.10(17) . . ?
N1 C10 C9 119.51(16) . . ?
C1 C10 C9 118.31(16) . . ?
N1 C11 C19 114.04(15) . . ?
N1 C11 C12 104.46(15) . . ?
C19 C11 C12 112.04(15) . . ?
N1 C11 H11 108.7 . . ?
C19 C11 H11 108.7 . . ?
C12 C11 H11 108.7 . . ?
O3 C12 C13 113.15(16) . . ?
O3 C12 C11 106.71(15) . . ?
C13 C12 C11 111.79(15) . . ?
O3 C12 H12 108.4 . . ?
C13 C12 H12 108.4 . . ?
C11 C12 H12 108.4 . . ?
C14 C13 C18 119.17(18) . . ?
C14 C13 C12 121.84(18) . . ?
C18 C13 C12 118.99(18) . . ?
C13 C14 C15 120.30(19) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C16 C15 C14 120.5(2) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 119.43(19) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 H16 120.3 . . ?
C18 C17 C16 120.2(2) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C17 C18 C13 120.41(19) . . ?
C17 C18 H18 119.8 . . ?
C13 C18 H18 119.8 . . ?
C20 C19 C24 119.47(17) . . ?
C20 C19 C11 118.80(17) . . ?
C24 C19 C11 121.63(17) . . ?
C19 C20 C21 120.51(19) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
C22 C21 C20 119.86(19) . . ?
C22 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
C23 C22 C21 119.81(18) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
C22 C23 C24 120.46(19) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 H23 119.8 . . ?
C19 C24 C23 119.88(19) . . ?
C19 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
N2 C25 C26 179.9(3) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 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
C10 C1 C2 O1 179.61(18) . . . . ?
Cl1 C1 C2 O1 -0.3(2) . . . . ?
C10 C1 C2 C3 -3.0(3) . . . . ?
Cl1 C1 C2 C3 177.11(13) . . . . ?
O1 C2 C3 C4 1.2(3) . . . . ?
C1 C2 C3 C4 -176.28(17) . . . . ?
O1 C2 C3 C8 179.79(17) . . . . ?
C1 C2 C3 C8 2.3(2) . . . . ?
C8 C3 C4 C5 -1.6(3) . . . . ?
C2 C3 C4 C5 176.94(17) . . . . ?
C3 C4 C5 C6 1.6(3) . . . . ?
C4 C5 C6 C7 -0.4(3) . . . . ?
C5 C6 C7 C8 -0.9(3) . . . . ?
C6 C7 C8 C3 0.9(3) . . . . ?
C6 C7 C8 C9 -179.02(17) . . . . ?
C4 C3 C8 C7 0.4(3) . . . . ?
C2 C3 C8 C7 -178.19(17) . . . . ?
C4 C3 C8 C9 -179.73(17) . . . . ?
C2 C3 C8 C9 1.7(3) . . . . ?
C7 C8 C9 O2 -6.8(3) . . . . ?
C3 C8 C9 O2 173.34(18) . . . . ?
C7 C8 C9 C10 174.85(16) . . . . ?
C3 C8 C9 C10 -5.1(3) . . . . ?
C11 N1 C10 C1 -164.90(19) . . . . ?
C11 N1 C10 C9 18.4(3) . . . . ?
C2 C1 C10 N1 -177.15(18) . . . . ?
Cl1 C1 C10 N1 2.8(3) . . . . ?
C2 C1 C10 C9 -0.4(3) . . . . ?
Cl1 C1 C10 C9 179.53(14) . . . . ?
O2 C9 C10 N1 2.8(3) . . . . ?
C8 C9 C10 N1 -178.77(17) . . . . ?
O2 C9 C10 C1 -174.03(18) . . . . ?
C8 C9 C10 C1 4.4(3) . . . . ?
C10 N1 C11 C19 -88.0(2) . . . . ?
C10 N1 C11 C12 149.4(2) . . . . ?
N1 C11 C12 O3 53.34(18) . . . . ?
C19 C11 C12 O3 -70.59(19) . . . . ?
N1 C11 C12 C13 177.53(16) . . . . ?
C19 C11 C12 C13 53.6(2) . . . . ?
O3 C12 C13 C14 19.1(2) . . . . ?
C11 C12 C13 C14 -101.4(2) . . . . ?
O3 C12 C13 C18 -162.25(16) . . . . ?
C11 C12 C13 C18 77.2(2) . . . . ?
C18 C13 C14 C15 0.7(3) . . . . ?
C12 C13 C14 C15 179.35(17) . . . . ?
C13 C14 C15 C16 -0.6(3) . . . . ?
C14 C15 C16 C17 0.1(3) . . . . ?
C15 C16 C17 C18 0.3(3) . . . . ?
C16 C17 C18 C13 -0.2(3) . . . . ?
C14 C13 C18 C17 -0.3(3) . . . . ?
C12 C13 C18 C17 -179.01(17) . . . . ?
N1 C11 C19 C20 142.90(18) . . . . ?
C12 C11 C19 C20 -98.7(2) . . . . ?
N1 C11 C19 C24 -40.9(2) . . . . ?
C12 C11 C19 C24 77.5(2) . . . . ?
C24 C19 C20 C21 -0.2(3) . . . . ?
C11 C19 C20 C21 176.12(17) . . . . ?
C19 C20 C21 C22 0.0(3) . . . . ?
C20 C21 C22 C23 0.3(3) . . . . ?
C21 C22 C23 C24 -0.4(3) . . . . ?
C20 C19 C24 C23 0.1(3) . . . . ?
C11 C19 C24 C23 -176.08(18) . . . . ?
C22 C23 C24 C19 0.2(3) . . . . ?

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
O3 H3 O1 0.82(3) 1.96(3) 2.7379(19) 160(2) 3_756 yes
N1 H1 Cl1 0.85(3) 2.54(2) 2.9600(17) 111.6(19) . yes
N1 H1 O3 0.85(3) 2.18(2) 2.649(2) 115(2) . yes

_refine_diff_density_max         0.195
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.041

