# 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 2022

####################################################################### 
# 
# 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_1_a
_database_code_depnum_ccdc_archive 'CCDC 2205670'
loop_
_audit_author_name
_audit_author_address
'He hangli'
;Wuhan Institute of Technology
China
;
_audit_update_record             
;
2022-09-07 deposited with the CCDC.	2022-11-07 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT340_1_a                 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01188 Ang.  
RESPONSE: This is caused by the poor diffraction of the sample.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H14 Cl2 N2 O5'
_chemical_formula_weight         421.22

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'
Cl Cl 0.1484 0.1585 '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                   13.1812(18)
_cell_length_b                   14.144(2)
_cell_length_c                   20.391(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3801.6(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3392
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      18.39

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_F_000             1728
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.376
_shelx_estimated_absorpt_T_min   0.929
_shelx_estimated_absorpt_T_max   0.929
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ccd
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32402
_diffrn_reflns_av_unetI/netI     0.1359
_diffrn_reflns_av_R_equivalents  0.1249
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.112
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6675
_reflns_number_gt                2768
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.787
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.998

_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-2014/7 (Sheldrick, 2014)'
_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)+(0.0850P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 857 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(6)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         6675
_refine_ls_number_parameters     477
_refine_ls_number_restraints     58
_refine_ls_R_factor_all          0.2151
_refine_ls_R_factor_gt           0.0690
_refine_ls_wR_factor_ref         0.1926
_refine_ls_wR_factor_gt          0.1484
_refine_ls_goodness_of_fit_ref   0.970
_refine_ls_restrained_S_all      0.973
_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
C1 C 0.2165(9) 0.6066(8) 0.9109(5) 0.072(3) Uani 1 1 d . . . . .
C2 C 0.2861(5) 0.6675(4) 0.9476(4) 0.066(3) Uani 1 1 d G . . . .
C3 C 0.2745(5) 0.7142(5) 1.0071(4) 0.075(3) Uani 1 1 d G . . . .
H3 H 0.2141 0.7087 1.0304 0.090 Uiso 1 1 calc R U . . .
C4 C 0.3533(7) 0.7689(5) 1.0319(3) 0.083(3) Uani 1 1 d G . . . .
H4 H 0.3455 0.8002 1.0717 0.100 Uiso 1 1 calc R U . . .
C5 C 0.4435(6) 0.7770(5) 0.9971(5) 0.089(4) Uani 1 1 d G . . . .
H5 H 0.4962 0.8137 1.0137 0.106 Uiso 1 1 calc R U . . .
C6 C 0.4551(5) 0.7303(6) 0.9376(4) 0.082(3) Uani 1 1 d G . . . .
H6 H 0.5155 0.7357 0.9143 0.098 Uiso 1 1 calc R U . . .
C7 C 0.3764(6) 0.6755(5) 0.9129(3) 0.067(3) Uani 1 1 d G . . . .
C8 C 0.3697(8) 0.6181(7) 0.8533(5) 0.065(3) Uani 1 1 d . . . . .
C9 C 0.2248(8) 0.4141(8) 0.7191(5) 0.074(3) Uani 1 1 d . . . . .
C10 C 0.2038(6) 0.4569(4) 0.6517(3) 0.064(3) Uani 1 1 d G . . . .
C15 C 0.2823(4) 0.4872(5) 0.6113(4) 0.067(3) Uani 1 1 d G . . . .
C14 C 0.2605(5) 0.5293(5) 0.5513(3) 0.072(3) Uani 1 1 d G . . . .
H14 H 0.3130 0.5495 0.5243 0.086 Uiso 1 1 calc R U . . .
C13 C 0.1603(6) 0.5410(4) 0.5318(3) 0.074(3) Uani 1 1 d G . . . .
C12 C 0.0818(4) 0.5107(5) 0.5722(4) 0.082(3) Uani 1 1 d G . . . .
H12 H 0.0148 0.5186 0.5591 0.098 Uiso 1 1 calc R U . . .
C11 C 0.1036(5) 0.4687(5) 0.6322(3) 0.076(3) Uani 1 1 d G . . . .
H11 H 0.0511 0.4484 0.6592 0.091 Uiso 1 1 calc R U . . .
C16 C 0.2917(10) 0.3240(8) 0.7146(7) 0.087(4) Uani 1 1 d . . . . .
C17 C 0.4112(11) 0.2320(10) 0.7721(7) 0.121(5) Uani 1 1 d . . . . .
H17A H 0.3727 0.1762 0.7600 0.146 Uiso 1 1 calc R U . . .
H17B H 0.4667 0.2387 0.7412 0.146 Uiso 1 1 calc R U . . .
C18 C 0.4513(12) 0.2204(11) 0.8373(6) 0.139(6) Uani 1 1 d . . . . .
H18A H 0.5030 0.1726 0.8369 0.208 Uiso 1 1 calc R U . . .
H18B H 0.3978 0.2019 0.8665 0.208 Uiso 1 1 calc R U . . .
H18C H 0.4800 0.2792 0.8519 0.208 Uiso 1 1 calc R U . . .
C19 C 0.6820(9) 0.3826(8) 0.6867(6) 0.079(3) Uani 1 1 d . . . . .
C20 C 0.7479(5) 0.3189(5) 0.7211(4) 0.070(3) Uani 1 1 d G . . . .
C21 C 0.7363(6) 0.2762(6) 0.7821(4) 0.086(3) Uani 1 1 d G . . . .
H21 H 0.6772 0.2858 0.8061 0.104 Uiso 1 1 calc R U . . .
C22 C 0.8130(8) 0.2193(5) 0.8071(3) 0.087(3) Uani 1 1 d G . . . .
H22 H 0.8053 0.1908 0.8479 0.104 Uiso 1 1 calc R U . . .
C23 C 0.9014(6) 0.2050(5) 0.7712(5) 0.097(4) Uani 1 1 d G . . . .
H23 H 0.9527 0.1669 0.7880 0.117 Uiso 1 1 calc R U . . .
C24 C 0.9130(5) 0.2476(6) 0.7103(4) 0.086(3) Uani 1 1 d G . . . .
H24 H 0.9721 0.2380 0.6862 0.103 Uiso 1 1 calc R U . . .
C25 C 0.8363(6) 0.3046(5) 0.6852(3) 0.068(3) Uani 1 1 d G . . . .
C26 C 0.8308(9) 0.3585(7) 0.6243(6) 0.070(3) Uani 1 1 d . . . . .
C27 C 0.6955(9) 0.5683(8) 0.4932(5) 0.073(3) Uani 1 1 d . . . . .
C28 C 0.6862(6) 0.5286(4) 0.4231(3) 0.065(3) Uani 1 1 d G . . . .
C33 C 0.7713(4) 0.5129(5) 0.3843(4) 0.068(3) Uani 1 1 d G . . . .
C32 C 0.7603(5) 0.4780(5) 0.3210(3) 0.076(3) Uani 1 1 d G . . . .
H32 H 0.8172 0.4675 0.2951 0.091 Uiso 1 1 calc R U . . .
C31 C 0.6641(6) 0.4587(4) 0.2965(3) 0.069(3) Uani 1 1 d G . . . .
C30 C 0.5790(5) 0.4744(5) 0.3352(4) 0.081(3) Uani 1 1 d G . . . .
H30 H 0.5146 0.4616 0.3188 0.097 Uiso 1 1 calc R U . . .
C29 C 0.5901(5) 0.5094(5) 0.3985(3) 0.073(3) Uani 1 1 d G . . . .
H29 H 0.5331 0.5199 0.4244 0.087 Uiso 1 1 calc R U . . .
C34 C 0.7577(11) 0.6616(9) 0.4922(7) 0.096(4) Uani 1 1 d . . . . .
C35A C 0.912(2) 0.735(2) 0.544(2) 0.123(6) Uani 0.44(2) 1 d D U P A 1
H35A H 0.9756 0.7039 0.5532 0.148 Uiso 0.44(2) 1 calc R U P A 1
H35B H 0.9167 0.7717 0.5040 0.148 Uiso 0.44(2) 1 calc R U P A 1
C36A C 0.875(4) 0.791(2) 0.5999(16) 0.126(8) Uani 0.44(2) 1 d D U P A 1
H36A H 0.9224 0.8411 0.6091 0.190 Uiso 0.44(2) 1 calc R U P A 1
H36B H 0.8100 0.8184 0.5893 0.190 Uiso 0.44(2) 1 calc R U P A 1
H36C H 0.8681 0.7515 0.6378 0.190 Uiso 0.44(2) 1 calc R U P A 1
C36B C 0.944(2) 0.751(2) 0.5958(14) 0.121(7) Uani 0.56(2) 1 d D U P A 2
H36D H 0.9808 0.8094 0.6005 0.181 Uiso 0.56(2) 1 calc R U P A 2
H36E H 0.9102 0.7365 0.6361 0.181 Uiso 0.56(2) 1 calc R U P A 2
H36F H 0.9912 0.7012 0.5854 0.181 Uiso 0.56(2) 1 calc R U P A 2
C35B C 0.869(2) 0.7601(15) 0.5425(16) 0.125(5) Uani 0.56(2) 1 d D U P A 2
H35C H 0.9016 0.7736 0.5008 0.150 Uiso 0.56(2) 1 calc R U P A 2
H35D H 0.8198 0.8091 0.5520 0.150 Uiso 0.56(2) 1 calc R U P A 2
Cl1 Cl 0.1330(2) 0.5905(2) 0.45743(13) 0.0963(10) Uani 1 1 d . . . . .
Cl2 Cl 0.4075(2) 0.4699(2) 0.63051(14) 0.0904(10) Uani 1 1 d . . . . .
Cl3 Cl 0.6524(3) 0.4203(3) 0.21643(14) 0.1081(11) Uani 1 1 d . . . . .
Cl4 Cl 0.8912(2) 0.5342(3) 0.41064(16) 0.1030(11) Uani 1 1 d . . . . .
N1 N 0.2723(7) 0.5794(6) 0.8549(4) 0.063(2) Uani 1 1 d . . . . .
N2 N 0.2276(6) 0.5125(6) 0.8135(5) 0.069(2) Uani 1 1 d . . . . .
C38 C 0.2767(8) 0.4890(7) 0.7631(5) 0.071(3) Uani 1 1 d . . . . .
H38 H 0.3397 0.5149 0.7530 0.085 Uiso 1 1 calc R U . . .
N4 N 0.7343(6) 0.4033(6) 0.6266(4) 0.065(2) Uani 1 1 d . . . . .
N5 N 0.6945(6) 0.4685(6) 0.5856(5) 0.072(2) Uani 1 1 d . . . . .
C37 C 0.7439(8) 0.4951(7) 0.5355(5) 0.069(3) Uani 1 1 d . . . . .
H37 H 0.8073 0.4701 0.5255 0.083 Uiso 1 1 calc R U . . .
O1 O 0.1329(6) 0.5800(6) 0.9238(4) 0.090(2) Uani 1 1 d . . . . .
O2 O 0.4308(6) 0.6061(6) 0.8116(4) 0.095(3) Uani 1 1 d . . . . .
O3 O 0.1340(5) 0.3826(5) 0.7470(3) 0.083(2) Uani 1 1 d . . . . .
H3A H 0.1250 0.4115 0.7814 0.125 Uiso 1 1 d R U . . .
O4 O 0.2886(8) 0.2718(6) 0.6709(4) 0.126(4) Uani 1 1 d . . . . .
O5 O 0.3462(6) 0.3147(5) 0.7686(4) 0.090(2) Uani 1 1 d . . . . .
O6 O 0.5995(6) 0.4105(7) 0.6996(4) 0.106(3) Uani 1 1 d . . . . .
O7 O 0.8913(5) 0.3650(5) 0.5813(4) 0.088(2) Uani 1 1 d . . . . .
O8 O 0.5985(7) 0.5917(6) 0.5163(4) 0.105(3) Uani 1 1 d . . . . .
H8 H 0.5888 0.5656 0.5516 0.158 Uiso 1 1 d R U . . .
O9 O 0.7467(9) 0.7202(6) 0.4520(5) 0.140(4) Uani 1 1 d . . . . .
O10 O 0.8214(7) 0.6646(5) 0.5426(5) 0.127(3) Uani 1 1 d D 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
C1 O1 1.193(12) . ?
C1 N1 1.412(12) . ?
C1 C2 1.464(12) . ?
C2 C3 1.3900 . ?
C2 C7 1.3900 . ?
C3 C4 1.3900 . ?
C3 H3 0.9300 . ?
C4 C5 1.3900 . ?
C4 H4 0.9300 . ?
C5 C6 1.3900 . ?
C5 H5 0.9300 . ?
C6 C7 1.3900 . ?
C6 H6 0.9300 . ?
C7 C8 1.465(12) . ?
C8 O2 1.182(10) . ?
C8 N1 1.396(13) . ?
C9 O3 1.397(11) . ?
C9 C10 1.527(11) . ?
C9 C38 1.547(13) . ?
C9 C16 1.552(15) . ?
C10 C15 1.3900 . ?
C10 C11 1.3900 . ?
C15 C14 1.3900 . ?
C15 Cl2 1.714(6) . ?
C14 C13 1.3900 . ?
C14 H14 0.9300 . ?
C13 C12 1.3900 . ?
C13 Cl1 1.708(6) . ?
C12 C11 1.3900 . ?
C12 H12 0.9300 . ?
C11 H11 0.9300 . ?
C16 O4 1.156(12) . ?
C16 O5 1.322(13) . ?
C17 C18 1.440(15) . ?
C17 O5 1.451(13) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 O6 1.186(12) . ?
C19 C20 1.436(12) . ?
C19 N4 1.436(13) . ?
C20 C21 1.3900 . ?
C20 C25 1.3900 . ?
C21 C22 1.3900 . ?
C21 H21 0.9300 . ?
C22 C23 1.3900 . ?
C22 H22 0.9300 . ?
C23 C24 1.3900 . ?
C23 H23 0.9300 . ?
C24 C25 1.3900 . ?
C24 H24 0.9300 . ?
C25 C26 1.459(12) . ?
C26 O7 1.190(12) . ?
C26 N4 1.422(13) . ?
C27 O8 1.402(12) . ?
C27 C37 1.490(13) . ?
C27 C28 1.542(11) . ?
C27 C34 1.553(16) . ?
C28 C33 1.3900 . ?
C28 C29 1.3900 . ?
C33 C32 1.3900 . ?
C33 Cl4 1.695(6) . ?
C32 C31 1.3900 . ?
C32 H32 0.9300 . ?
C31 C30 1.3900 . ?
C31 Cl3 1.727(6) . ?
C30 C29 1.3900 . ?
C30 H30 0.9300 . ?
C29 H29 0.9300 . ?
C34 O9 1.174(13) . ?
C34 O10 1.328(14) . ?
C35A C36A 1.47(3) . ?
C35A O10 1.55(2) . ?
C35A H35A 0.9700 . ?
C35A H35B 0.9700 . ?
C36A H36A 0.9600 . ?
C36A H36B 0.9600 . ?
C36A H36C 0.9600 . ?
C36B C35B 1.48(2) . ?
C36B H36D 0.9600 . ?
C36B H36E 0.9600 . ?
C36B H36F 0.9600 . ?
C35B O10 1.490(19) . ?
C35B H35C 0.9700 . ?
C35B H35D 0.9700 . ?
N1 N2 1.399(10) . ?
N2 C38 1.260(11) . ?
C38 H38 0.9300 . ?
N4 N5 1.350(10) . ?
N5 C37 1.269(12) . ?
C37 H37 0.9300 . ?
O3 H3A 0.8199 . ?
O8 H8 0.8201 . ?

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 C1 N1 125.0(11) . . ?
O1 C1 C2 130.7(11) . . ?
N1 C1 C2 104.3(9) . . ?
C3 C2 C7 120.0 . . ?
C3 C2 C1 131.1(8) . . ?
C7 C2 C1 108.9(8) . . ?
C2 C3 C4 120.0 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C5 120.0 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 120.0 . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C7 120.0 . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C6 C7 C2 120.0 . . ?
C6 C7 C8 130.9(7) . . ?
C2 C7 C8 109.0(7) . . ?
O2 C8 N1 125.9(10) . . ?
O2 C8 C7 129.4(10) . . ?
N1 C8 C7 104.6(9) . . ?
O3 C9 C10 109.7(8) . . ?
O3 C9 C38 111.2(9) . . ?
C10 C9 C38 109.3(8) . . ?
O3 C9 C16 104.4(9) . . ?
C10 C9 C16 111.9(9) . . ?
C38 C9 C16 110.2(9) . . ?
C15 C10 C11 120.0 . . ?
C15 C10 C9 121.4(6) . . ?
C11 C10 C9 118.5(6) . . ?
C14 C15 C10 120.0 . . ?
C14 C15 Cl2 117.5(5) . . ?
C10 C15 Cl2 122.5(5) . . ?
C15 C14 C13 120.0 . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C13 C12 120.0 . . ?
C14 C13 Cl1 120.3(5) . . ?
C12 C13 Cl1 119.7(5) . . ?
C11 C12 C13 120.0 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C12 C11 C10 120.0 . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
O4 C16 O5 126.6(12) . . ?
O4 C16 C9 123.4(12) . . ?
O5 C16 C9 109.9(10) . . ?
C18 C17 O5 110.7(11) . . ?
C18 C17 H17A 109.5 . . ?
O5 C17 H17A 109.5 . . ?
C18 C17 H17B 109.5 . . ?
O5 C17 H17B 109.5 . . ?
H17A C17 H17B 108.1 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O6 C19 C20 130.9(12) . . ?
O6 C19 N4 124.2(11) . . ?
C20 C19 N4 104.8(10) . . ?
C21 C20 C25 120.0 . . ?
C21 C20 C19 130.0(8) . . ?
C25 C20 C19 109.9(8) . . ?
C20 C21 C22 120.0 . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C23 C22 C21 120.0 . . ?
C23 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C24 C23 C22 120.0 . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C23 C24 C25 120.0 . . ?
C23 C24 H24 120.0 . . ?
C25 C24 H24 120.0 . . ?
C24 C25 C20 120.0 . . ?
C24 C25 C26 130.7(8) . . ?
C20 C25 C26 109.3(8) . . ?
O7 C26 N4 126.0(10) . . ?
O7 C26 C25 129.5(11) . . ?
N4 C26 C25 104.5(9) . . ?
O8 C27 C37 111.1(9) . . ?
O8 C27 C28 108.9(8) . . ?
C37 C27 C28 108.5(8) . . ?
O8 C27 C34 106.6(9) . . ?
C37 C27 C34 111.9(10) . . ?
C28 C27 C34 109.8(9) . . ?
C33 C28 C29 120.0 . . ?
C33 C28 C27 121.4(7) . . ?
C29 C28 C27 118.6(7) . . ?
C28 C33 C32 120.0 . . ?
C28 C33 Cl4 122.9(5) . . ?
C32 C33 Cl4 117.1(5) . . ?
C31 C32 C33 120.0 . . ?
C31 C32 H32 120.0 . . ?
C33 C32 H32 120.0 . . ?
C32 C31 C30 120.0 . . ?
C32 C31 Cl3 118.9(5) . . ?
C30 C31 Cl3 121.0(5) . . ?
C31 C30 C29 120.0 . . ?
C31 C30 H30 120.0 . . ?
C29 C30 H30 120.0 . . ?
C30 C29 C28 120.0 . . ?
C30 C29 H29 120.0 . . ?
C28 C29 H29 120.0 . . ?
O9 C34 O10 126.5(13) . . ?
O9 C34 C27 123.0(13) . . ?
O10 C34 C27 110.5(11) . . ?
C36A C35A O10 96(2) . . ?
C36A C35A H35A 112.5 . . ?
O10 C35A H35A 112.5 . . ?
C36A C35A H35B 112.5 . . ?
O10 C35A H35B 112.5 . . ?
H35A C35A H35B 110.0 . . ?
C35A C36A H36A 109.5 . . ?
C35A C36A H36B 109.5 . . ?
H36A C36A H36B 109.5 . . ?
C35A C36A H36C 109.5 . . ?
H36A C36A H36C 109.5 . . ?
H36B C36A H36C 109.5 . . ?
C35B C36B H36D 109.5 . . ?
C35B C36B H36E 109.5 . . ?
H36D C36B H36E 109.5 . . ?
C35B C36B H36F 109.5 . . ?
H36D C36B H36F 109.5 . . ?
H36E C36B H36F 109.5 . . ?
C36B C35B O10 101.8(17) . . ?
C36B C35B H35C 111.4 . . ?
O10 C35B H35C 111.4 . . ?
C36B C35B H35D 111.4 . . ?
O10 C35B H35D 111.4 . . ?
H35C C35B H35D 109.3 . . ?
C8 N1 N2 129.7(9) . . ?
C8 N1 C1 113.1(9) . . ?
N2 N1 C1 116.9(9) . . ?
C38 N2 N1 117.0(8) . . ?
N2 C38 C9 115.2(10) . . ?
N2 C38 H38 122.4 . . ?
C9 C38 H38 122.4 . . ?
N5 N4 C26 129.2(9) . . ?
N5 N4 C19 118.8(9) . . ?
C26 N4 C19 111.4(9) . . ?
C37 N5 N4 120.1(9) . . ?
N5 C37 C27 116.9(10) . . ?
N5 C37 H37 121.5 . . ?
C27 C37 H37 121.5 . . ?
C9 O3 H3A 108.2 . . ?
C16 O5 C17 116.3(9) . . ?
C27 O8 H8 109.3 . . ?
C34 O10 C35B 107.2(12) . . ?
C34 O10 C35A 121.4(19) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -2.0(16) . . . . ?
N1 C1 C2 C3 -179.0(5) . . . . ?
O1 C1 C2 C7 178.2(10) . . . . ?
N1 C1 C2 C7 1.2(8) . . . . ?
C7 C2 C3 C4 0.0 . . . . ?
C1 C2 C3 C4 -179.8(8) . . . . ?
C2 C3 C4 C5 0.0 . . . . ?
C3 C4 C5 C6 0.0 . . . . ?
C4 C5 C6 C7 0.0 . . . . ?
C5 C6 C7 C2 0.0 . . . . ?
C5 C6 C7 C8 -178.3(8) . . . . ?
C3 C2 C7 C6 0.0 . . . . ?
C1 C2 C7 C6 179.8(6) . . . . ?
C3 C2 C7 C8 178.6(6) . . . . ?
C1 C2 C7 C8 -1.6(7) . . . . ?
C6 C7 C8 O2 -1.0(15) . . . . ?
C2 C7 C8 O2 -179.4(10) . . . . ?
C6 C7 C8 N1 179.7(5) . . . . ?
C2 C7 C8 N1 1.3(8) . . . . ?
O3 C9 C10 C15 -175.1(6) . . . . ?
C38 C9 C10 C15 62.7(9) . . . . ?
C16 C9 C10 C15 -59.7(10) . . . . ?
O3 C9 C10 C11 7.5(9) . . . . ?
C38 C9 C10 C11 -114.7(8) . . . . ?
C16 C9 C10 C11 122.9(8) . . . . ?
C11 C10 C15 C14 0.0 . . . . ?
C9 C10 C15 C14 -177.4(7) . . . . ?
C11 C10 C15 Cl2 -176.8(5) . . . . ?
C9 C10 C15 Cl2 5.8(7) . . . . ?
C10 C15 C14 C13 0.0 . . . . ?
Cl2 C15 C14 C13 177.0(5) . . . . ?
C15 C14 C13 C12 0.0 . . . . ?
C15 C14 C13 Cl1 -178.6(5) . . . . ?
C14 C13 C12 C11 0.0 . . . . ?
Cl1 C13 C12 C11 178.7(5) . . . . ?
C13 C12 C11 C10 0.0 . . . . ?
C15 C10 C11 C12 0.0 . . . . ?
C9 C10 C11 C12 177.5(7) . . . . ?
O3 C9 C16 O4 85.9(15) . . . . ?
C10 C9 C16 O4 -32.7(16) . . . . ?
C38 C9 C16 O4 -154.6(13) . . . . ?
O3 C9 C16 O5 -90.7(10) . . . . ?
C10 C9 C16 O5 150.7(9) . . . . ?
C38 C9 C16 O5 28.9(13) . . . . ?
O6 C19 C20 C21 -4.8(16) . . . . ?
N4 C19 C20 C21 179.5(5) . . . . ?
O6 C19 C20 C25 177.7(11) . . . . ?
N4 C19 C20 C25 2.0(8) . . . . ?
C25 C20 C21 C22 0.0 . . . . ?
C19 C20 C21 C22 -177.3(8) . . . . ?
C20 C21 C22 C23 0.0 . . . . ?
C21 C22 C23 C24 0.0 . . . . ?
C22 C23 C24 C25 0.0 . . . . ?
C23 C24 C25 C20 0.0 . . . . ?
C23 C24 C25 C26 178.1(8) . . . . ?
C21 C20 C25 C24 0.0 . . . . ?
C19 C20 C25 C24 177.8(7) . . . . ?
C21 C20 C25 C26 -178.5(7) . . . . ?
C19 C20 C25 C26 -0.7(7) . . . . ?
C24 C25 C26 O7 1.2(15) . . . . ?
C20 C25 C26 O7 179.5(10) . . . . ?
C24 C25 C26 N4 -179.2(5) . . . . ?
C20 C25 C26 N4 -0.9(8) . . . . ?
O8 C27 C28 C33 170.1(6) . . . . ?
C37 C27 C28 C33 -68.8(10) . . . . ?
C34 C27 C28 C33 53.8(10) . . . . ?
O8 C27 C28 C29 -9.2(10) . . . . ?
C37 C27 C28 C29 111.9(8) . . . . ?
C34 C27 C28 C29 -125.6(8) . . . . ?
C29 C28 C33 C32 0.0 . . . . ?
C27 C28 C33 C32 -179.3(7) . . . . ?
C29 C28 C33 Cl4 -179.8(6) . . . . ?
C27 C28 C33 Cl4 0.9(7) . . . . ?
C28 C33 C32 C31 0.0 . . . . ?
Cl4 C33 C32 C31 179.8(5) . . . . ?
C33 C32 C31 C30 0.0 . . . . ?
C33 C32 C31 Cl3 177.2(5) . . . . ?
C32 C31 C30 C29 0.0 . . . . ?
Cl3 C31 C30 C29 -177.2(5) . . . . ?
C31 C30 C29 C28 0.0 . . . . ?
C33 C28 C29 C30 0.0 . . . . ?
C27 C28 C29 C30 179.4(7) . . . . ?
O8 C27 C34 O9 -75.6(15) . . . . ?
C37 C27 C34 O9 162.8(13) . . . . ?
C28 C27 C34 O9 42.2(17) . . . . ?
O8 C27 C34 O10 103.5(11) . . . . ?
C37 C27 C34 O10 -18.1(14) . . . . ?
C28 C27 C34 O10 -138.7(10) . . . . ?
O2 C8 N1 N2 6.9(16) . . . . ?
C7 C8 N1 N2 -173.8(7) . . . . ?
O2 C8 N1 C1 -179.9(10) . . . . ?
C7 C8 N1 C1 -0.6(10) . . . . ?
O1 C1 N1 C8 -177.6(10) . . . . ?
C2 C1 N1 C8 -0.3(10) . . . . ?
O1 C1 N1 N2 -3.4(14) . . . . ?
C2 C1 N1 N2 173.8(7) . . . . ?
C8 N1 N2 C38 -7.8(13) . . . . ?
C1 N1 N2 C38 179.2(9) . . . . ?
N1 N2 C38 C9 179.4(8) . . . . ?
O3 C9 C38 N2 -3.6(13) . . . . ?
C10 C9 C38 N2 117.7(9) . . . . ?
C16 C9 C38 N2 -118.9(10) . . . . ?
O7 C26 N4 N5 -7.5(16) . . . . ?
C25 C26 N4 N5 173.0(8) . . . . ?
O7 C26 N4 C19 -178.2(10) . . . . ?
C25 C26 N4 C19 2.3(10) . . . . ?
O6 C19 N4 N5 9.5(15) . . . . ?
C20 C19 N4 N5 -174.5(7) . . . . ?
O6 C19 N4 C26 -178.7(11) . . . . ?
C20 C19 N4 C26 -2.7(10) . . . . ?
C26 N4 N5 C37 2.9(14) . . . . ?
C19 N4 N5 C37 173.0(9) . . . . ?
N4 N5 C37 C27 -179.2(8) . . . . ?
O8 C27 C37 N5 -2.8(13) . . . . ?
C28 C27 C37 N5 -122.6(10) . . . . ?
C34 C27 C37 N5 116.2(11) . . . . ?
O4 C16 O5 C17 2(2) . . . . ?
C9 C16 O5 C17 178.7(10) . . . . ?
C18 C17 O5 C16 -169.1(13) . . . . ?
O9 C34 O10 C35B 5(3) . . . . ?
C27 C34 O10 C35B -173.6(18) . . . . ?
O9 C34 O10 C35A -17(2) . . . . ?
C27 C34 O10 C35A 163.5(16) . . . . ?
C36B C35B O10 C34 -175(3) . . . . ?
C36A C35A O10 C34 114(3) . . . . ?

_refine_diff_density_max         0.223
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.051

####################################################################### 
# 
# 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_1_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2205769'
loop_
_audit_author_name
_audit_author_address
'He hangli'
;Wuhan Institute of Technology
China
;
_audit_update_record             
;
2022-09-07 deposited with the CCDC.	2022-11-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H17 Cl2 N3 O4'
_chemical_formula_weight         434.26

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.740
_cell_length_b                   19.007
_cell_length_c                   8.976
_cell_angle_alpha                90
_cell_angle_beta                 95.31
_cell_angle_gamma                90
_cell_volume                     1994.2
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3488
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      19.78

_exptl_crystal_description       Block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_F_000             896
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.358
_shelx_estimated_absorpt_T_min   0.932
_shelx_estimated_absorpt_T_max   0.932
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ccd
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6914
_diffrn_reflns_av_unetI/netI     0.0654
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.143
_diffrn_reflns_theta_max         25.064
_diffrn_reflns_theta_full        25.064
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3536
_reflns_number_gt                2265
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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-2014/7 (Sheldrick, 2014)'
_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)+(0.0511P)²+0.0660P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3536
_refine_ls_number_parameters     264
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1256
_refine_ls_R_factor_gt           0.0644
_refine_ls_wR_factor_ref         0.1288
_refine_ls_wR_factor_gt          0.1111
_refine_ls_goodness_of_fit_ref   1.138
_refine_ls_restrained_S_all      1.138
_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
C7 C 0.5042(2) 0.40136(14) 0.2247(3) 0.0395(7) Uani 1 1 d . . . . .
H7 H 0.5350 0.3767 0.3154 0.047 Uiso 1 1 calc R U . . .
C15 C 0.8943(2) 0.51528(15) 0.6757(3) 0.0433(8) Uani 1 1 d . . . . .
C11 C 0.5746(3) 0.50999(15) 0.3463(3) 0.0408(7) Uani 1 1 d . . . . .
C8 C 0.5861(2) 0.39078(17) 0.1047(3) 0.0432(8) Uani 1 1 d . . . . .
C6 C 0.3885(2) 0.36989(14) 0.1729(3) 0.0372(7) Uani 1 1 d . . . . .
C5 C 0.3211(3) 0.40144(16) 0.0575(3) 0.0479(8) Uani 1 1 d . . . . .
H5 H 0.3491 0.4406 0.0107 0.057 Uiso 1 1 calc R U . . .
C14 C 0.9116(3) 0.56511(15) 0.5685(3) 0.0437(8) Uani 1 1 d . . . . .
C13 C 0.8169(3) 0.56062(16) 0.4492(4) 0.0467(8) Uani 1 1 d . . . . .
C20 C 0.7873(3) 0.47753(17) 0.6294(3) 0.0469(8) Uani 1 1 d . . . . .
C1 C 0.3450(3) 0.30992(15) 0.2353(3) 0.0449(8) Uani 1 1 d . . . . .
C12 C 0.5522(3) 0.58653(15) 0.3674(4) 0.0548(9) Uani 1 1 d . . . . .
H12A H 0.5906 0.6019 0.4608 0.082 Uiso 1 1 calc R U . . .
H12B H 0.4714 0.5942 0.3679 0.082 Uiso 1 1 calc R U . . .
H12C H 0.5803 0.6127 0.2869 0.082 Uiso 1 1 calc R U . . .
C16 C 0.9737(3) 0.50455(17) 0.7950(3) 0.0545(9) Uani 1 1 d . . . . .
H16 H 0.9621 0.4708 0.8671 0.065 Uiso 1 1 calc R U . . .
C3 C 0.1741(3) 0.31814(17) 0.0769(4) 0.0533(9) Uani 1 1 d . . . . .
C4 C 0.2137(3) 0.37668(17) 0.0095(3) 0.0545(9) Uani 1 1 d . . . . .
H4 H 0.1690 0.3993 -0.0671 0.065 Uiso 1 1 calc R U . . .
C2 C 0.2380(3) 0.28401(16) 0.1886(4) 0.0553(9) Uani 1 1 d . . . . .
H2 H 0.2101 0.2440 0.2326 0.066 Uiso 1 1 calc R U . . .
C19 C 1.0096(3) 0.60540(16) 0.5776(4) 0.0566(9) Uani 1 1 d . . . . .
H19 H 1.0214 0.6387 0.5047 0.068 Uiso 1 1 calc R U . . .
C17 C 1.0720(3) 0.54537(18) 0.8054(4) 0.0613(10) Uani 1 1 d . . . . .
H17 H 1.1268 0.5393 0.8861 0.074 Uiso 1 1 calc R U . . .
C18 C 1.0896(3) 0.59485(18) 0.6977(4) 0.0617(10) Uani 1 1 d . . . . .
H18 H 1.1563 0.6215 0.7062 0.074 Uiso 1 1 calc R U . . .
C9 C 0.7008(3) 0.30786(18) -0.0080(4) 0.0685(10) Uani 1 1 d . . . . .
H9A H 0.7653 0.3399 -0.0049 0.082 Uiso 1 1 calc R U . . .
H9B H 0.6589 0.3109 -0.1061 0.082 Uiso 1 1 calc R U . . .
C10 C 0.7413(3) 0.23454(18) 0.0219(5) 0.0931(13) Uani 1 1 d . . . . .
H10A H 0.7841 0.2324 0.1182 0.140 Uiso 1 1 calc R U . . .
H10B H 0.7893 0.2204 -0.0538 0.140 Uiso 1 1 calc R U . . .
H10C H 0.6767 0.2035 0.0204 0.140 Uiso 1 1 calc R U . . .
Cl1 Cl 0.03820(8) 0.28753(6) 0.01652(13) 0.0964(4) Uani 1 1 d . . . . .
Cl2 Cl 0.42499(8) 0.26396(4) 0.37629(9) 0.0690(3) Uani 1 1 d . . . . .
N1 N 0.49246(19) 0.47478(11) 0.2600(3) 0.0435(6) Uani 1 1 d . . . . .
H1 H 0.4318 0.4969 0.2254 0.052 Uiso 1 1 calc R U . . .
N2 N 0.6601(2) 0.47294(13) 0.4020(3) 0.0460(7) Uani 1 1 d . . . . .
N3 N 0.7431(2) 0.50960(12) 0.4956(3) 0.0446(6) Uani 1 1 d . . . . .
O1 O 0.62700(18) 0.32590(11) 0.1075(2) 0.0572(6) Uani 1 1 d . . . . .
O2 O 0.60928(19) 0.43443(12) 0.0170(3) 0.0645(7) Uani 1 1 d . . . . .
O3 O 0.74490(19) 0.42861(12) 0.6887(3) 0.0661(7) Uani 1 1 d . . . . .
O4 O 0.80332(19) 0.59287(12) 0.3332(3) 0.0642(6) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C7 N1 1.440(3) . ?
C7 C6 1.517(4) . ?
C7 C8 1.522(4) . ?
C7 H7 0.9800 . ?
C15 C16 1.368(4) . ?
C15 C14 1.379(4) . ?
C15 C20 1.473(4) . ?
C11 N2 1.288(3) . ?
C11 N1 1.357(3) . ?
C11 C12 1.493(4) . ?
C8 O2 1.192(3) . ?
C8 O1 1.323(3) . ?
C6 C5 1.381(4) . ?
C6 C1 1.388(4) . ?
C5 C4 1.377(4) . ?
C5 H5 0.9300 . ?
C14 C19 1.378(4) . ?
C14 C13 1.472(4) . ?
C13 O4 1.206(3) . ?
C13 N3 1.390(4) . ?
C20 O3 1.201(3) . ?
C20 N3 1.403(4) . ?
C1 C2 1.377(4) . ?
C1 Cl2 1.740(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C16 C17 1.386(4) . ?
C16 H16 0.9300 . ?
C3 C2 1.361(4) . ?
C3 C4 1.368(4) . ?
C3 Cl1 1.737(3) . ?
C4 H4 0.9300 . ?
C2 H2 0.9300 . ?
C19 C18 1.377(4) . ?
C19 H19 0.9300 . ?
C17 C18 1.378(4) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C9 O1 1.452(4) . ?
C9 C10 1.489(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
N1 H1 0.8600 . ?
N2 N3 1.411(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
N1 C7 C6 110.3(2) . . ?
N1 C7 C8 111.3(2) . . ?
C6 C7 C8 109.7(2) . . ?
N1 C7 H7 108.5 . . ?
C6 C7 H7 108.5 . . ?
C8 C7 H7 108.5 . . ?
C16 C15 C14 121.0(3) . . ?
C16 C15 C20 130.5(3) . . ?
C14 C15 C20 108.3(3) . . ?
N2 C11 N1 116.0(3) . . ?
N2 C11 C12 128.6(3) . . ?
N1 C11 C12 115.4(3) . . ?
O2 C8 O1 123.8(3) . . ?
O2 C8 C7 125.0(3) . . ?
O1 C8 C7 111.2(3) . . ?
C5 C6 C1 116.9(3) . . ?
C5 C6 C7 119.6(3) . . ?
C1 C6 C7 123.5(2) . . ?
C4 C5 C6 122.1(3) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
C19 C14 C15 121.1(3) . . ?
C19 C14 C13 130.2(3) . . ?
C15 C14 C13 108.5(3) . . ?
O4 C13 N3 125.2(3) . . ?
O4 C13 C14 129.0(3) . . ?
N3 C13 C14 105.8(3) . . ?
O3 C20 N3 125.4(3) . . ?
O3 C20 C15 129.0(3) . . ?
N3 C20 C15 105.6(3) . . ?
C2 C1 C6 122.0(3) . . ?
C2 C1 Cl2 117.2(2) . . ?
C6 C1 Cl2 120.8(2) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C15 C16 C17 118.2(3) . . ?
C15 C16 H16 120.9 . . ?
C17 C16 H16 120.9 . . ?
C2 C3 C4 121.8(3) . . ?
C2 C3 Cl1 119.9(3) . . ?
C4 C3 Cl1 118.3(3) . . ?
C3 C4 C5 118.6(3) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
C3 C2 C1 118.6(3) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C18 C19 C14 118.1(3) . . ?
C18 C19 H19 121.0 . . ?
C14 C19 H19 121.0 . . ?
C18 C17 C16 120.8(3) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C19 C18 C17 120.9(3) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
O1 C9 C10 107.1(3) . . ?
O1 C9 H9A 110.3 . . ?
C10 C9 H9A 110.3 . . ?
O1 C9 H9B 110.3 . . ?
C10 C9 H9B 110.3 . . ?
H9A C9 H9B 108.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C11 N1 C7 121.7(2) . . ?
C11 N1 H1 119.1 . . ?
C7 N1 H1 119.1 . . ?
C11 N2 N3 115.5(2) . . ?
C13 N3 C20 111.6(2) . . ?
C13 N3 N2 125.6(2) . . ?
C20 N3 N2 118.4(2) . . ?
C8 O1 C9 116.5(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
N1 C7 C8 O2 -22.6(4) . . . . ?
C6 C7 C8 O2 99.8(3) . . . . ?
N1 C7 C8 O1 158.8(2) . . . . ?
C6 C7 C8 O1 -78.8(3) . . . . ?
N1 C7 C6 C5 53.3(3) . . . . ?
C8 C7 C6 C5 -69.7(3) . . . . ?
N1 C7 C6 C1 -126.8(3) . . . . ?
C8 C7 C6 C1 110.2(3) . . . . ?
C1 C6 C5 C4 2.5(4) . . . . ?
C7 C6 C5 C4 -177.6(3) . . . . ?
C16 C15 C14 C19 0.3(5) . . . . ?
C20 C15 C14 C19 -175.7(3) . . . . ?
C16 C15 C14 C13 175.5(3) . . . . ?
C20 C15 C14 C13 -0.5(3) . . . . ?
C19 C14 C13 O4 -1.8(6) . . . . ?
C15 C14 C13 O4 -176.4(3) . . . . ?
C19 C14 C13 N3 177.6(3) . . . . ?
C15 C14 C13 N3 3.0(3) . . . . ?
C16 C15 C20 O3 1.0(6) . . . . ?
C14 C15 C20 O3 176.6(3) . . . . ?
C16 C15 C20 N3 -177.7(3) . . . . ?
C14 C15 C20 N3 -2.1(3) . . . . ?
C5 C6 C1 C2 -2.2(4) . . . . ?
C7 C6 C1 C2 178.0(3) . . . . ?
C5 C6 C1 Cl2 177.4(2) . . . . ?
C7 C6 C1 Cl2 -2.5(4) . . . . ?
C14 C15 C16 C17 0.2(5) . . . . ?
C20 C15 C16 C17 175.3(3) . . . . ?
C2 C3 C4 C5 -0.3(5) . . . . ?
Cl1 C3 C4 C5 179.6(2) . . . . ?
C6 C5 C4 C3 -1.3(5) . . . . ?
C4 C3 C2 C1 0.6(5) . . . . ?
Cl1 C3 C2 C1 -179.3(2) . . . . ?
C6 C1 C2 C3 0.7(5) . . . . ?
Cl2 C1 C2 C3 -179.0(2) . . . . ?
C15 C14 C19 C18 -0.5(5) . . . . ?
C13 C14 C19 C18 -174.5(3) . . . . ?
C15 C16 C17 C18 -0.6(5) . . . . ?
C14 C19 C18 C17 0.1(5) . . . . ?
C16 C17 C18 C19 0.5(5) . . . . ?
N2 C11 N1 C7 -4.0(4) . . . . ?
C12 C11 N1 C7 177.4(3) . . . . ?
C6 C7 N1 C11 161.3(2) . . . . ?
C8 C7 N1 C11 -76.6(3) . . . . ?
N1 C11 N2 N3 -178.0(2) . . . . ?
C12 C11 N2 N3 0.3(4) . . . . ?
O4 C13 N3 C20 175.0(3) . . . . ?
C14 C13 N3 C20 -4.4(3) . . . . ?
O4 C13 N3 N2 19.1(5) . . . . ?
C14 C13 N3 N2 -160.3(2) . . . . ?
O3 C20 N3 C13 -174.6(3) . . . . ?
C15 C20 N3 C13 4.1(3) . . . . ?
O3 C20 N3 N2 -16.8(4) . . . . ?
C15 C20 N3 N2 161.9(2) . . . . ?
C11 N2 N3 C13 -69.0(4) . . . . ?
C11 N2 N3 C20 136.7(3) . . . . ?
O2 C8 O1 C9 -2.4(4) . . . . ?
C7 C8 O1 C9 176.3(2) . . . . ?
C10 C9 O1 C8 177.0(3) . . . . ?

_refine_diff_density_max         0.185
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.045

