# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2020

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1955556'
loop_
_audit_author_name
_audit_author_address
'Yan-Tuan Li'
;School of Medicine and Pharmacy and College of Marine Life Science, Ocean University of China
China
;
_audit_update_record             
;
2019-12-13 deposited with the CCDC.	2020-01-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'1-(4-Chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetic acid L-proline'
_chemical_name_common            'indomethacin L-proline'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H27 Cl N2 O7'
_chemical_formula_weight         490.92

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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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, y+1/2, -z'

_cell_length_a                   12.4240(5)
_cell_length_b                   5.7358(2)
_cell_length_c                   16.3820(6)
_cell_angle_alpha                90
_cell_angle_beta                 101.436(4)
_cell_angle_gamma                90
_cell_volume                     1144.23(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3591
_cell_measurement_theta_min      4.098
_cell_measurement_theta_max      73.363

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_F_000             516
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.903
_shelx_estimated_absorpt_T_min   0.599
_shelx_estimated_absorpt_T_max   0.832
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  Bruker
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7252
_diffrn_reflns_av_unetI/netI     0.0713
_diffrn_reflns_av_R_equivalents  0.0690
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         4.098
_diffrn_reflns_theta_max         73.363
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.785
_diffrn_reflns_point_group_measured_fraction_full 0.812
_reflns_number_total             3591
_reflns_number_gt                3276
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.448
_reflns_Friedel_fraction_max     0.543
_reflns_Friedel_fraction_full    0.579

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1596P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_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 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.08(4)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         3591
_refine_ls_number_parameters     319
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0841
_refine_ls_R_factor_gt           0.0788
_refine_ls_wR_factor_ref         0.2096
_refine_ls_wR_factor_gt          0.2035
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.000
_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 0.90359(12) 0.6317(3) -0.15670(9) 0.0272(4) Uani 1 1 d . . . . .
O1 O 0.4386(3) 0.0353(7) 0.1167(3) 0.0210(9) Uani 1 1 d . . . . .
O2 O 0.8199(3) 1.1070(7) 0.1951(2) 0.0210(9) Uani 1 1 d . . . . .
O3 O 0.4378(3) 0.6365(8) 0.3978(3) 0.0270(10) Uani 1 1 d . . . . .
O4 O 0.5557(4) 0.9303(7) 0.4145(3) 0.0240(10) Uani 1 1 d . . . . .
H4 H 0.492(6) 1.015(8) 0.417(5) 0.036 Uiso 1 1 calc R U . . .
N1 N 0.7284(4) 0.7660(8) 0.2078(3) 0.0150(10) Uani 1 1 d . . . . .
C1 C 0.7264(4) 0.7780(10) 0.2943(3) 0.0143(11) Uani 1 1 d . . . . .
C2 C 0.6601(4) 0.6067(10) 0.3128(3) 0.0145(11) Uani 1 1 d . . . . .
C3 C 0.6153(4) 0.4793(10) 0.2370(3) 0.0135(11) Uani 1 1 d . . . . .
C4 C 0.6580(4) 0.5799(9) 0.1729(3) 0.0125(10) Uani 1 1 d . . . . .
C5 C 0.6222(5) 0.5070(11) 0.0901(3) 0.0162(11) Uani 1 1 d . . . . .
H5 H 0.647593 0.580911 0.045566 0.019 Uiso 1 1 calc R U . . .
C6 C 0.5491(5) 0.3246(11) 0.0760(3) 0.0158(11) Uani 1 1 d . . . . .
H6 H 0.524323 0.271332 0.020519 0.019 Uiso 1 1 calc R U . . .
C7 C 0.5101(5) 0.2151(11) 0.1405(4) 0.0179(12) Uani 1 1 d . . . . .
C8 C 0.5411(5) 0.2936(11) 0.2220(3) 0.0170(12) Uani 1 1 d . . . . .
H8 H 0.512989 0.223612 0.266023 0.020 Uiso 1 1 calc R U . . .
C9 C 0.7864(4) 0.9161(10) 0.1661(3) 0.0133(11) Uani 1 1 d . . . . .
C10 C 0.8111(4) 0.8390(10) 0.0849(3) 0.0149(11) Uani 1 1 d . . . . .
C11 C 0.8595(4) 0.6206(11) 0.0776(3) 0.0160(11) Uani 1 1 d . . . . .
H11 H 0.871797 0.515257 0.123211 0.019 Uiso 1 1 calc R U . . .
C12 C 0.8889(5) 0.5605(10) 0.0033(4) 0.0181(12) Uani 1 1 d . . . . .
H12 H 0.924592 0.416139 -0.001489 0.022 Uiso 1 1 calc R U . . .
C13 C 0.8667(5) 0.7094(10) -0.0635(4) 0.0178(12) Uani 1 1 d . . . . .
C14 C 0.8171(5) 0.9228(12) -0.0585(4) 0.0210(12) Uani 1 1 d . . . . .
H14 H 0.801484 1.022718 -0.105630 0.025 Uiso 1 1 calc R U . . .
C15 C 0.7900(5) 0.9898(10) 0.0174(4) 0.0188(12) Uani 1 1 d . . . . .
H15 H 0.757342 1.137504 0.022454 0.023 Uiso 1 1 calc R U . . .
C16 C 0.7887(5) 0.9547(11) 0.3518(4) 0.0192(12) Uani 1 1 d . . . . .
H16A H 0.776972 0.927457 0.408467 0.029 Uiso 1 1 calc R U . . .
H16B H 0.762984 1.111335 0.333631 0.029 Uiso 1 1 calc R U . . .
H16C H 0.867197 0.941436 0.351175 0.029 Uiso 1 1 calc R U . . .
C17 C 0.6291(5) 0.5599(11) 0.3958(3) 0.0178(12) Uani 1 1 d . . . . .
H17A H 0.691747 0.597331 0.441500 0.021 Uiso 1 1 calc R U . . .
H17B H 0.610712 0.393012 0.400150 0.021 Uiso 1 1 calc R U . . .
C18 C 0.5311(5) 0.7092(11) 0.4034(3) 0.0185(12) Uani 1 1 d . . . . .
C19 C 0.3986(5) -0.0851(12) 0.1806(4) 0.0239(13) Uani 1 1 d . . . . .
H19A H 0.460673 -0.142660 0.222188 0.036 Uiso 1 1 calc R U . . .
H19B H 0.353155 -0.217021 0.156244 0.036 Uiso 1 1 calc R U . . .
H19C H 0.354361 0.021336 0.207194 0.036 Uiso 1 1 calc R U . . .
O5 O 0.1899(3) 1.0876(7) 0.4241(3) 0.0203(9) Uani 1 1 d . . . . .
O6 O 0.0551(4) 0.9173(8) 0.4736(3) 0.0292(11) Uani 1 1 d . . . . .
N2 N 0.0840(4) 0.4992(8) 0.4176(3) 0.0150(10) Uani 1 1 d . . . . .
H2A H 0.047277 0.543661 0.457886 0.018 Uiso 1 1 calc R U . . .
H2B H 0.115420 0.357764 0.431827 0.018 Uiso 1 1 calc R U . . .
C20 C 0.1707(4) 0.6753(10) 0.4100(3) 0.0147(11) Uani 1 1 d . . . . .
H20 H 0.243618 0.628395 0.443745 0.018 Uiso 1 1 calc R U . . .
C21 C 0.1723(5) 0.6722(11) 0.3171(3) 0.0172(11) Uani 1 1 d . . . . .
H21A H 0.214133 0.536927 0.302313 0.021 Uiso 1 1 calc R U . . .
H21B H 0.204225 0.817554 0.299558 0.021 Uiso 1 1 calc R U . . .
C22 C 0.0504(5) 0.6520(12) 0.2782(3) 0.0199(12) Uani 1 1 d . . . . .
H22A H 0.013604 0.805458 0.276963 0.024 Uiso 1 1 calc R U . . .
H22B H 0.039825 0.590288 0.220744 0.024 Uiso 1 1 calc R U . . .
C23 C 0.0058(5) 0.4831(11) 0.3348(4) 0.0212(12) Uani 1 1 d . . . . .
H23A H -0.069313 0.528196 0.340357 0.025 Uiso 1 1 calc R U . . .
H23B H 0.003879 0.322432 0.312536 0.025 Uiso 1 1 calc R U . . .
C24 C 0.1337(5) 0.9139(10) 0.4392(3) 0.0155(11) Uani 1 1 d . . . . .
O7 O 0.3847(4) 1.1795(8) 0.3810(3) 0.0278(10) Uani 1 1 d D . . . .
H7B H 0.327(5) 1.13(2) 0.397(6) 0.06(3) Uiso 1 1 d D . . . .
H7A H 0.394(7) 1.327(5) 0.385(5) 0.03(2) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C13 1.737(6) . ?
O1 C7 1.366(7) . ?
O1 C19 1.423(7) . ?
O2 C9 1.232(7) . ?
O3 C18 1.218(7) . ?
O4 C18 1.309(8) . ?
O4 H4 0.93(9) . ?
N1 C9 1.387(7) . ?
N1 C1 1.424(7) . ?
N1 C4 1.426(7) . ?
C1 C2 1.354(8) . ?
C1 C16 1.492(7) . ?
C2 C3 1.453(7) . ?
C2 C17 1.510(7) . ?
C3 C4 1.391(7) . ?
C3 C8 1.398(8) . ?
C4 C5 1.405(7) . ?
C5 C6 1.375(8) . ?
C5 H5 0.9500 . ?
C6 C7 1.396(8) . ?
C6 H6 0.9500 . ?
C7 C8 1.390(8) . ?
C8 H8 0.9500 . ?
C9 C10 1.490(7) . ?
C10 C15 1.388(8) . ?
C10 C11 1.404(8) . ?
C11 C12 1.382(8) . ?
C11 H11 0.9500 . ?
C12 C13 1.373(8) . ?
C12 H12 0.9500 . ?
C13 C14 1.380(9) . ?
C14 C15 1.405(8) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.513(8) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
O5 C24 1.269(7) . ?
O6 C24 1.220(7) . ?
N2 C20 1.500(7) . ?
N2 C23 1.506(7) . ?
N2 H2A 0.9100 . ?
N2 H2B 0.9100 . ?
C20 C21 1.526(7) . ?
C20 C24 1.549(8) . ?
C20 H20 1.0000 . ?
C21 C22 1.527(8) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.519(8) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
O7 H7B 0.86(3) . ?
O7 H7A 0.85(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O1 C19 117.4(5) . . ?
C18 O4 H4 109.5 . . ?
C9 N1 C1 125.0(5) . . ?
C9 N1 C4 127.2(5) . . ?
C1 N1 C4 107.7(4) . . ?
C2 C1 N1 108.5(5) . . ?
C2 C1 C16 127.9(5) . . ?
N1 C1 C16 123.5(5) . . ?
C1 C2 C3 108.8(5) . . ?
C1 C2 C17 127.2(5) . . ?
C3 C2 C17 123.9(5) . . ?
C4 C3 C8 121.4(5) . . ?
C4 C3 C2 107.3(5) . . ?
C8 C3 C2 131.3(5) . . ?
C3 C4 C5 120.7(5) . . ?
C3 C4 N1 107.7(4) . . ?
C5 C4 N1 131.4(5) . . ?
C6 C5 C4 117.4(5) . . ?
C6 C5 H5 121.3 . . ?
C4 C5 H5 121.3 . . ?
C5 C6 C7 122.1(5) . . ?
C5 C6 H6 118.9 . . ?
C7 C6 H6 118.9 . . ?
O1 C7 C8 124.0(5) . . ?
O1 C7 C6 115.3(5) . . ?
C8 C7 C6 120.7(5) . . ?
C7 C8 C3 117.6(5) . . ?
C7 C8 H8 121.2 . . ?
C3 C8 H8 121.2 . . ?
O2 C9 N1 122.0(5) . . ?
O2 C9 C10 119.6(5) . . ?
N1 C9 C10 118.3(5) . . ?
C15 C10 C11 120.3(5) . . ?
C15 C10 C9 119.1(5) . . ?
C11 C10 C9 120.6(5) . . ?
C12 C11 C10 119.4(5) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C13 C12 C11 120.0(6) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C14 121.7(5) . . ?
C12 C13 Cl1 119.6(5) . . ?
C14 C13 Cl1 118.6(5) . . ?
C13 C14 C15 118.9(6) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
C10 C15 C14 119.6(5) . . ?
C10 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C1 C16 H16A 109.5 . . ?
C1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C2 C17 C18 109.0(5) . . ?
C2 C17 H17A 109.9 . . ?
C18 C17 H17A 109.9 . . ?
C2 C17 H17B 109.9 . . ?
C18 C17 H17B 109.9 . . ?
H17A C17 H17B 108.3 . . ?
O3 C18 O4 122.3(6) . . ?
O3 C18 C17 124.7(6) . . ?
O4 C18 C17 113.0(5) . . ?
O1 C19 H19A 109.5 . . ?
O1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C20 N2 C23 108.2(4) . . ?
C20 N2 H2A 110.1 . . ?
C23 N2 H2A 110.1 . . ?
C20 N2 H2B 110.1 . . ?
C23 N2 H2B 110.1 . . ?
H2A N2 H2B 108.4 . . ?
N2 C20 C21 103.1(4) . . ?
N2 C20 C24 107.9(4) . . ?
C21 C20 C24 112.4(5) . . ?
N2 C20 H20 111.0 . . ?
C21 C20 H20 111.0 . . ?
C24 C20 H20 111.0 . . ?
C20 C21 C22 102.1(4) . . ?
C20 C21 H21A 111.4 . . ?
C22 C21 H21A 111.4 . . ?
C20 C21 H21B 111.4 . . ?
C22 C21 H21B 111.4 . . ?
H21A C21 H21B 109.2 . . ?
C23 C22 C21 104.2(4) . . ?
C23 C22 H22A 110.9 . . ?
C21 C22 H22A 110.9 . . ?
C23 C22 H22B 110.9 . . ?
C21 C22 H22B 110.9 . . ?
H22A C22 H22B 108.9 . . ?
N2 C23 C22 105.2(5) . . ?
N2 C23 H23A 110.7 . . ?
C22 C23 H23A 110.7 . . ?
N2 C23 H23B 110.7 . . ?
C22 C23 H23B 110.7 . . ?
H23A C23 H23B 108.8 . . ?
O6 C24 O5 126.8(5) . . ?
O6 C24 C20 118.1(5) . . ?
O5 C24 C20 115.1(5) . . ?
H7B O7 H7A 114(10) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 N1 C1 C2 179.1(5) . . . . ?
C4 N1 C1 C2 1.1(6) . . . . ?
C9 N1 C1 C16 -0.9(8) . . . . ?
C4 N1 C1 C16 -178.9(5) . . . . ?
N1 C1 C2 C3 -0.9(6) . . . . ?
C16 C1 C2 C3 179.0(5) . . . . ?
N1 C1 C2 C17 -176.9(5) . . . . ?
C16 C1 C2 C17 3.1(9) . . . . ?
C1 C2 C3 C4 0.5(6) . . . . ?
C17 C2 C3 C4 176.6(5) . . . . ?
C1 C2 C3 C8 -177.9(6) . . . . ?
C17 C2 C3 C8 -1.8(10) . . . . ?
C8 C3 C4 C5 4.1(8) . . . . ?
C2 C3 C4 C5 -174.5(5) . . . . ?
C8 C3 C4 N1 178.8(5) . . . . ?
C2 C3 C4 N1 0.2(6) . . . . ?
C9 N1 C4 C3 -178.7(5) . . . . ?
C1 N1 C4 C3 -0.8(6) . . . . ?
C9 N1 C4 C5 -4.8(9) . . . . ?
C1 N1 C4 C5 173.1(6) . . . . ?
C3 C4 C5 C6 -3.8(8) . . . . ?
N1 C4 C5 C6 -177.1(6) . . . . ?
C4 C5 C6 C7 0.6(8) . . . . ?
C19 O1 C7 C8 -3.4(9) . . . . ?
C19 O1 C7 C6 178.6(5) . . . . ?
C5 C6 C7 O1 -179.5(5) . . . . ?
C5 C6 C7 C8 2.5(9) . . . . ?
O1 C7 C8 C3 179.9(5) . . . . ?
C6 C7 C8 C3 -2.2(8) . . . . ?
C4 C3 C8 C7 -1.0(8) . . . . ?
C2 C3 C8 C7 177.2(6) . . . . ?
C1 N1 C9 O2 -18.2(9) . . . . ?
C4 N1 C9 O2 159.4(5) . . . . ?
C1 N1 C9 C10 160.1(5) . . . . ?
C4 N1 C9 C10 -22.3(8) . . . . ?
O2 C9 C10 C15 -49.7(7) . . . . ?
N1 C9 C10 C15 131.9(6) . . . . ?
O2 C9 C10 C11 127.6(6) . . . . ?
N1 C9 C10 C11 -50.7(7) . . . . ?
C15 C10 C11 C12 2.0(8) . . . . ?
C9 C10 C11 C12 -175.2(5) . . . . ?
C10 C11 C12 C13 -2.8(8) . . . . ?
C11 C12 C13 C14 1.4(9) . . . . ?
C11 C12 C13 Cl1 -179.8(4) . . . . ?
C12 C13 C14 C15 0.8(9) . . . . ?
Cl1 C13 C14 C15 -178.1(4) . . . . ?
C11 C10 C15 C14 0.1(9) . . . . ?
C9 C10 C15 C14 177.4(5) . . . . ?
C13 C14 C15 C10 -1.5(9) . . . . ?
C1 C2 C17 C18 85.8(7) . . . . ?
C3 C2 C17 C18 -89.6(7) . . . . ?
C2 C17 C18 O3 106.2(6) . . . . ?
C2 C17 C18 O4 -72.0(6) . . . . ?
C23 N2 C20 C21 -25.5(6) . . . . ?
C23 N2 C20 C24 93.7(5) . . . . ?
N2 C20 C21 C22 39.7(6) . . . . ?
C24 C20 C21 C22 -76.2(6) . . . . ?
C20 C21 C22 C23 -39.6(6) . . . . ?
C20 N2 C23 C22 0.9(6) . . . . ?
C21 C22 C23 N2 24.1(6) . . . . ?
N2 C20 C24 O6 10.6(7) . . . . ?
C21 C20 C24 O6 123.6(6) . . . . ?
N2 C20 C24 O5 -169.4(5) . . . . ?
C21 C20 C24 O5 -56.4(6) . . . . ?

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
O4 H4 O7 0.93 1.65 2.528(7) 155.5 . yes
O7 H7A O3 0.85(3) 1.86(3) 2.704(7) 171(8) 1_565 yes
O7 H7B O5 0.86(3) 1.86(3) 2.703(6) 168(11) . yes
N2 H2B O5 0.91 1.82 2.694(6) 159.7 1_545 yes
N2 H2A O6 0.91 1.99 2.759(6) 140.8 2_546 yes
C17 H17A O5 0.99 2.39 3.339(7) 159.6 2_646 yes

_refine_diff_density_max         0.820
_refine_diff_density_min         -0.548
_refine_diff_density_rms         0.118

