# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 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_Form_I_disorder
_database_code_depnum_ccdc_archive 'CCDC 2181218'
_audit_update_record             
;
2022-06-22 deposited with the CCDC.	2022-07-18 downloaded from the CCDC.
;

_audit_creation_date             2022-06-21T11:31:28-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C15 H9.31 O2, C6 H3 N3 O6, C5 H5.69 Cl N2'
_chemical_formula_sum            'C26 H18 Cl N5 O8'
_chemical_formula_weight         563.9

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.1140(2)
_cell_length_b                   9.7490(3)
_cell_length_c                   18.0972(5)
_cell_angle_alpha                88.738(2)
_cell_angle_beta                 81.565(2)
_cell_angle_gamma                89.703(2)
_cell_volume                     1241.24(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9516
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      27.73
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.495
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.098
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             580
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2 -1 1 0.243
-4 3 -2 0.205
0 0 -1 0.046
0 0 1 0.059
-3 1 2 0.2
1 0 -1 0.211
2 0 -1 0.228
-3 -1 0 0.207
1 0 1 0.244
0 3 1 0.046
0 1 -2 0.057
0 -1 2 0.078
-1 -3 -2 0.102
0 -1 -1 0.047
0 -2 -1 0.057
0 1 1 0.049
-1 0 3 0.133
-1 -4 3 0.071

_exptl_special_details           
;
 Absorption corrections were made using the program SADABS
        (Sheldrick, 1996)
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.217
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_correction_T_min  0.7108
_exptl_absorpt_correction_T_max  0.7457
_shelx_estimated_absorpt_T_min   0.9
_shelx_estimated_absorpt_T_max   0.979

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'Bruker D8 Venture Photon CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.039
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_number            47374
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.089
_diffrn_reflns_theta_max         27.992
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 1
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 1
_reflns_Friedel_coverage         0
_reflns_number_total             5991
_reflns_number_gt                4379
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2016)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker 2016)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'Ortep for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2006)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     'dual - dual-space method e.g. SHELXD'
_atom_sites_solution_secondary   'dual - dual-space method e.g. SHELXD'
_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0480P)²+0.3374P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5991
_refine_ls_number_parameters     371
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0403
_refine_ls_wR_factor_ref         0.1091
_refine_ls_wR_factor_gt          0.0988
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.047

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'

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 0.8273(2) 0.52668(15) 0.16876(8) 0.0227(3) Uani 1 1 d . . . . .
C2 C 0.8052(2) 0.53685(16) 0.24550(9) 0.0257(3) Uani 1 1 d . . . . .
H2 H 0.830128 0.461194 0.276633 0.031 Uiso 1 1 calc R U . . .
C3 C 0.7455(2) 0.66134(16) 0.27496(8) 0.0259(3) Uani 1 1 d . . . . .
C4 C 0.7048(2) 0.77350(16) 0.23171(9) 0.0267(3) Uani 1 1 d . . . . .
H4 H 0.663345 0.858284 0.253425 0.032 Uiso 1 1 calc R U . . .
C5 C 0.7275(2) 0.75594(15) 0.15572(9) 0.0253(3) Uani 1 1 d . . . . .
C6 C 0.7905(2) 0.63457(15) 0.12193(8) 0.0240(3) Uani 1 1 d . . . . .
H6 H 0.80769 0.625851 0.069188 0.029 Uiso 1 1 calc R U . . .
N1 N 0.89350(18) 0.39538(13) 0.13513(8) 0.0287(3) Uani 1 1 d . . . . .
N2 N 0.72865(19) 0.67711(17) 0.35629(8) 0.0353(3) Uani 1 1 d . . . . .
N3 N 0.68515(19) 0.87260(14) 0.10748(9) 0.0343(3) Uani 1 1 d . . . . .
O1 O 0.91762(18) 0.38812(13) 0.06716(7) 0.0401(3) Uani 1 1 d . . . . .
O2 O 0.92087(19) 0.30071(12) 0.17782(7) 0.0424(3) Uani 1 1 d . . . . .
O3 O 0.69395(18) 0.57479(15) 0.39612(7) 0.0468(3) Uani 1 1 d . . . . .
O4 O 0.75225(18) 0.79270(15) 0.37862(7) 0.0464(3) Uani 1 1 d . . . . .
O5 O 0.6377(2) 0.98047(13) 0.13827(8) 0.0521(4) Uani 1 1 d . . . . .
O6 O 0.6999(2) 0.85447(14) 0.04067(7) 0.0491(3) Uani 1 1 d . . . . .
C7 C 0.2348(2) 0.63602(15) 0.33025(8) 0.0226(3) Uani 1 1 d . . . . .
C8 C 0.25555(19) 0.63815(14) 0.24605(7) 0.0189(3) Uani 1 1 d . . . . .
C9 C 0.31442(18) 0.51817(14) 0.20660(8) 0.0189(3) Uani 1 1 d . . . . .
C10 C 0.3661(2) 0.39400(15) 0.24223(8) 0.0241(3) Uani 1 1 d . . . . .
H10 H 0.360761 0.390098 0.294997 0.029 Uiso 1 1 calc R U . . .
C11 C 0.4229(2) 0.28110(16) 0.20149(9) 0.0283(3) Uani 1 1 d . . . . .
H11 H 0.45738 0.199968 0.226326 0.034 Uiso 1 1 calc R U . . .
C12 C 0.4312(2) 0.28286(16) 0.12272(9) 0.0295(3) Uani 1 1 d . . . . .
H12 H 0.469668 0.203083 0.095209 0.035 Uiso 1 1 calc R U . . .
C13 C 0.3843(2) 0.39834(15) 0.08686(8) 0.0251(3) Uani 1 1 d . . . . .
H13 H 0.389769 0.398485 0.034094 0.03 Uiso 1 1 calc R U . . .
C14 C 0.32681(19) 0.52022(14) 0.12658(8) 0.0200(3) Uani 1 1 d . . . . .
C15 C 0.2818(2) 0.63979(15) 0.08956(8) 0.0215(3) Uani 1 1 d . . . . .
H15 H 0.2892 0.639999 0.036712 0.026 Uiso 1 1 calc R U . . .
C16 C 0.22614(19) 0.75928(14) 0.12777(8) 0.0209(3) Uani 1 1 d . . . . .
C17 C 0.1808(2) 0.88147(15) 0.08873(9) 0.0264(3) Uani 1 1 d . . . . .
H17 H 0.190554 0.881878 0.035808 0.032 Uiso 1 1 calc R U . . .
C18 C 0.1240(2) 0.99698(16) 0.12655(9) 0.0303(4) Uani 1 1 d . . . . .
H18 H 0.095424 1.077841 0.10008 0.036 Uiso 1 1 calc R U . . .
C19 C 0.1074(2) 0.99649(16) 0.20545(9) 0.0287(3) Uani 1 1 d . . . . .
H19 H 0.066383 1.077424 0.231425 0.034 Uiso 1 1 calc R U . . .
C20 C 0.1489(2) 0.88294(15) 0.24490(8) 0.0243(3) Uani 1 1 d . . . . .
H20 H 0.13598 0.885673 0.297845 0.029 Uiso 1 1 calc R U . . .
C21 C 0.21197(19) 0.75897(14) 0.20766(8) 0.0198(3) Uani 1 1 d . . . . .
O7 O 0.33834(15) 0.71971(12) 0.35873(6) 0.0303(3) Uani 1 1 d . . . . .
H7 H 0.298197 0.726749 0.404511 0.045 Uiso 0.31(3) 1 calc R U P A 2
O8 O 0.11800(16) 0.55623(12) 0.36628(6) 0.0324(3) Uani 1 1 d . . . . .
C22 C 0.1268(2) 0.72194(15) 0.54669(8) 0.0268(3) Uani 1 1 d . . . . .
C23 C 0.1121(2) 0.75497(17) 0.62298(9) 0.0301(4) Uani 1 1 d . . . . .
H23 H 0.000794 0.731335 0.656497 0.036 Uiso 1 1 calc R U . . .
C24 C 0.2575(2) 0.82066(17) 0.64828(9) 0.0312(4) Uani 1 1 d . . . . .
H24 H 0.247803 0.843799 0.699424 0.037 Uiso 1 1 calc R U . . .
C25 C 0.4216(2) 0.85405(17) 0.59854(9) 0.0309(4) Uani 1 1 d . . . . .
C26 C 0.4324(2) 0.82101(17) 0.52571(9) 0.0326(4) Uani 1 1 d . . . . .
H26 H 0.543418 0.843475 0.491775 0.039 Uiso 1 1 calc R U . . .
N4 N 0.28691(19) 0.75642(13) 0.50081(7) 0.0292(3) Uani 1 1 d . . . . .
H4A H 0.297087 0.736317 0.45322 0.035 Uiso 0.69(3) 1 calc R U P A 1
N5 N -0.0128(2) 0.66124(16) 0.51784(9) 0.0362(3) Uani 1 1 d . . . . .
Cl1 Cl 0.60717(7) 0.93963(5) 0.62901(3) 0.04846(15) Uani 1 1 d . . . . .
H5A H 0.012(3) 0.635(2) 0.4709(12) 0.045(6) Uiso 1 1 d . . . . .
H5B H -0.101(3) 0.619(2) 0.5508(12) 0.051(6) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C2 1.380(2) . ?
C1 C6 1.384(2) . ?
C1 N1 1.4747(19) . ?
C2 C3 1.376(2) . ?
C2 H2 0.95 . ?
C3 C4 1.385(2) . ?
C3 N2 1.470(2) . ?
C4 C5 1.375(2) . ?
C4 H4 0.95 . ?
C5 C6 1.386(2) . ?
C5 N3 1.4751(19) . ?
C6 H6 0.95 . ?
N1 O1 1.2204(17) . ?
N1 O2 1.2237(17) . ?
N2 O3 1.2224(19) . ?
N2 O4 1.2261(19) . ?
N3 O6 1.2150(18) . ?
N3 O5 1.2236(19) . ?
C7 O8 1.2434(17) . ?
C7 O7 1.2688(17) . ?
C7 C8 1.5090(19) . ?
C8 C21 1.4105(19) . ?
C8 C9 1.4133(19) . ?
C9 C10 1.431(2) . ?
C9 C14 1.4374(19) . ?
C10 C11 1.365(2) . ?
C10 H10 0.95 . ?
C11 C12 1.418(2) . ?
C11 H11 0.95 . ?
C12 C13 1.352(2) . ?
C12 H12 0.95 . ?
C13 C14 1.429(2) . ?
C13 H13 0.95 . ?
C14 C15 1.391(2) . ?
C15 C16 1.394(2) . ?
C15 H15 0.95 . ?
C16 C17 1.431(2) . ?
C16 C21 1.4344(19) . ?
C17 C18 1.359(2) . ?
C17 H17 0.95 . ?
C18 C19 1.415(2) . ?
C18 H18 0.95 . ?
C19 C20 1.359(2) . ?
C19 H19 0.95 . ?
C20 C21 1.434(2) . ?
C20 H20 0.95 . ?
O7 H7 0.84 . ?
C22 N5 1.335(2) . ?
C22 N4 1.347(2) . ?
C22 C23 1.413(2) . ?
C23 C24 1.360(2) . ?
C23 H23 0.95 . ?
C24 C25 1.401(2) . ?
C24 H24 0.95 . ?
C25 C26 1.355(2) . ?
C25 Cl1 1.7286(16) . ?
C26 N4 1.352(2) . ?
C26 H26 0.95 . ?
N4 H4A 0.88 . ?
N5 H5A 0.89(2) . ?
N5 H5B 0.90(2) . ?

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
C2 C1 C6 122.84(14) . . ?
C2 C1 N1 118.63(13) . . ?
C6 C1 N1 118.53(13) . . ?
C3 C2 C1 117.11(14) . . ?
C3 C2 H2 121.4 . . ?
C1 C2 H2 121.4 . . ?
C2 C3 C4 123.31(14) . . ?
C2 C3 N2 118.35(14) . . ?
C4 C3 N2 118.32(14) . . ?
C5 C4 C3 116.62(14) . . ?
C5 C4 H4 121.7 . . ?
C3 C4 H4 121.7 . . ?
C4 C5 C6 123.33(14) . . ?
C4 C5 N3 118.48(14) . . ?
C6 C5 N3 118.18(14) . . ?
C1 C6 C5 116.77(14) . . ?
C1 C6 H6 121.6 . . ?
C5 C6 H6 121.6 . . ?
O1 N1 O2 124.43(14) . . ?
O1 N1 C1 118.33(13) . . ?
O2 N1 C1 117.24(13) . . ?
O3 N2 O4 125.22(15) . . ?
O3 N2 C3 117.93(15) . . ?
O4 N2 C3 116.85(14) . . ?
O6 N3 O5 125.15(15) . . ?
O6 N3 C5 117.84(14) . . ?
O5 N3 C5 117.02(15) . . ?
O8 C7 O7 125.08(13) . . ?
O8 C7 C8 118.91(12) . . ?
O7 C7 C8 116.01(12) . . ?
C21 C8 C9 120.71(12) . . ?
C21 C8 C7 119.64(12) . . ?
C9 C8 C7 119.64(12) . . ?
C8 C9 C10 123.23(13) . . ?
C8 C9 C14 119.03(12) . . ?
C10 C9 C14 117.73(12) . . ?
C11 C10 C9 120.93(14) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C10 C11 C12 121.09(14) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C13 C12 C11 119.84(14) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C14 121.45(14) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 H13 119.3 . . ?
C15 C14 C13 121.45(13) . . ?
C15 C14 C9 119.60(12) . . ?
C13 C14 C9 118.94(13) . . ?
C14 C15 C16 121.88(13) . . ?
C14 C15 H15 119.1 . . ?
C16 C15 H15 119.1 . . ?
C15 C16 C17 121.12(13) . . ?
C15 C16 C21 119.30(13) . . ?
C17 C16 C21 119.57(13) . . ?
C18 C17 C16 120.72(14) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C17 C18 C19 119.85(14) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
C20 C19 C18 121.52(14) . . ?
C20 C19 H19 119.2 . . ?
C18 C19 H19 119.2 . . ?
C19 C20 C21 120.87(14) . . ?
C19 C20 H20 119.6 . . ?
C21 C20 H20 119.6 . . ?
C8 C21 C16 119.47(12) . . ?
C8 C21 C20 123.06(13) . . ?
C16 C21 C20 117.46(13) . . ?
C7 O7 H7 109.5 . . ?
N5 C22 N4 118.62(14) . . ?
N5 C22 C23 122.86(15) . . ?
N4 C22 C23 118.50(14) . . ?
C24 C23 C22 119.85(15) . . ?
C24 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C23 C24 C25 119.65(14) . . ?
C23 C24 H24 120.2 . . ?
C25 C24 H24 120.2 . . ?
C26 C25 C24 119.35(15) . . ?
C26 C25 Cl1 120.07(13) . . ?
C24 C25 Cl1 120.57(12) . . ?
N4 C26 C25 120.72(15) . . ?
N4 C26 H26 119.6 . . ?
C25 C26 H26 119.6 . . ?
C22 N4 C26 121.93(13) . . ?
C22 N4 H4A 119 . . ?
C26 N4 H4A 119 . . ?
C22 N5 H5A 117.5(13) . . ?
C22 N5 H5B 115.7(13) . . ?
H5A N5 H5B 121.3(18) . . ?

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
C6 C1 C2 C3 -0.6(2) . . . . ?
N1 C1 C2 C3 179.18(13) . . . . ?
C1 C2 C3 C4 1.0(2) . . . . ?
C1 C2 C3 N2 -177.41(13) . . . . ?
C2 C3 C4 C5 -0.3(2) . . . . ?
N2 C3 C4 C5 178.20(13) . . . . ?
C3 C4 C5 C6 -1.1(2) . . . . ?
C3 C4 C5 N3 179.82(13) . . . . ?
C2 C1 C6 C5 -0.6(2) . . . . ?
N1 C1 C6 C5 179.63(13) . . . . ?
C4 C5 C6 C1 1.5(2) . . . . ?
N3 C5 C6 C1 -179.41(12) . . . . ?
C2 C1 N1 O1 -178.07(13) . . . . ?
C6 C1 N1 O1 1.7(2) . . . . ?
C2 C1 N1 O2 1.8(2) . . . . ?
C6 C1 N1 O2 -178.40(13) . . . . ?
C2 C3 N2 O3 -28.3(2) . . . . ?
C4 C3 N2 O3 153.18(14) . . . . ?
C2 C3 N2 O4 151.15(14) . . . . ?
C4 C3 N2 O4 -27.38(19) . . . . ?
C4 C5 N3 O6 -177.70(14) . . . . ?
C6 C5 N3 O6 3.1(2) . . . . ?
C4 C5 N3 O5 2.3(2) . . . . ?
C6 C5 N3 O5 -176.87(14) . . . . ?
O8 C7 C8 C21 117.32(15) . . . . ?
O7 C7 C8 C21 -61.45(18) . . . . ?
O8 C7 C8 C9 -61.29(18) . . . . ?
O7 C7 C8 C9 119.94(15) . . . . ?
C21 C8 C9 C10 178.02(12) . . . . ?
C7 C8 C9 C10 -3.4(2) . . . . ?
C21 C8 C9 C14 -0.88(19) . . . . ?
C7 C8 C9 C14 177.72(12) . . . . ?
C8 C9 C10 C11 -179.69(13) . . . . ?
C14 C9 C10 C11 -0.8(2) . . . . ?
C9 C10 C11 C12 -0.5(2) . . . . ?
C10 C11 C12 C13 0.7(2) . . . . ?
C11 C12 C13 C14 0.3(2) . . . . ?
C12 C13 C14 C15 178.85(14) . . . . ?
C12 C13 C14 C9 -1.5(2) . . . . ?
C8 C9 C14 C15 0.32(19) . . . . ?
C10 C9 C14 C15 -178.64(12) . . . . ?
C8 C9 C14 C13 -179.32(12) . . . . ?
C10 C9 C14 C13 1.73(19) . . . . ?
C13 C14 C15 C16 -179.79(13) . . . . ?
C9 C14 C15 C16 0.6(2) . . . . ?
C14 C15 C16 C17 179.84(13) . . . . ?
C14 C15 C16 C21 -0.9(2) . . . . ?
C15 C16 C17 C18 179.03(14) . . . . ?
C21 C16 C17 C18 -0.2(2) . . . . ?
C16 C17 C18 C19 -0.6(2) . . . . ?
C17 C18 C19 C20 0.6(2) . . . . ?
C18 C19 C20 C21 0.2(2) . . . . ?
C9 C8 C21 C16 0.55(19) . . . . ?
C7 C8 C21 C16 -178.05(12) . . . . ?
C9 C8 C21 C20 179.05(13) . . . . ?
C7 C8 C21 C20 0.5(2) . . . . ?
C15 C16 C21 C8 0.35(19) . . . . ?
C17 C16 C21 C8 179.60(13) . . . . ?
C15 C16 C21 C20 -178.24(13) . . . . ?
C17 C16 C21 C20 1.01(19) . . . . ?
C19 C20 C21 C8 -179.56(13) . . . . ?
C19 C20 C21 C16 -1.0(2) . . . . ?
N5 C22 C23 C24 -177.96(16) . . . . ?
N4 C22 C23 C24 0.3(2) . . . . ?
C22 C23 C24 C25 -0.5(2) . . . . ?
C23 C24 C25 C26 0.4(3) . . . . ?
C23 C24 C25 Cl1 179.11(13) . . . . ?
C24 C25 C26 N4 0.0(3) . . . . ?
Cl1 C25 C26 N4 -178.73(13) . . . . ?
N5 C22 N4 C26 178.42(15) . . . . ?
C23 C22 N4 C26 0.1(2) . . . . ?
C25 C26 N4 C22 -0.2(2) . . . . ?

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
N5 H5B O8 0.90(2) 2.24(2) 2.9687(19) 138(2) 2_566 yes
N4 H4A O7 0.88 1.7 2.5762(16) 171 . yes
O7 H7 N4 0.84 1.76 2.5762(16) 162 . yes



# END of CIF
####################################################################### 
# 
# 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_Form_II_disorder
_database_code_depnum_ccdc_archive 'CCDC 2181219'
_audit_update_record             
;
2022-06-22 deposited with the CCDC.	2022-07-18 downloaded from the CCDC.
;

_audit_creation_date             2022-06-21T12:04:19-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C15 H9.69 O2, C6 H3 N3 O6, C5 H5.31 Cl N2'
_chemical_formula_sum            'C26 H18 Cl N5 O8'
_chemical_formula_weight         563.9

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.9341(5)
_cell_length_b                   7.2129(4)
_cell_length_c                   38.172(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.311(2)
_cell_angle_gamma                90
_cell_volume                     2452.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    9839
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      36.49
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       cube
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.404
_exptl_crystal_size_mid          0.291
_exptl_crystal_size_min          0.276
_exptl_crystal_density_diffrn    1.527
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1160
_exptl_special_details           
;
 Absorption corrections were made using the program SADABS
        (Sheldrick, 1996)
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.22
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_correction_T_min  0.7007
_exptl_absorpt_correction_T_max  0.7471
_shelx_estimated_absorpt_T_min   0.917
_shelx_estimated_absorpt_T_max   0.942

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'Bruker D8 Venture Photon CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.014
_diffrn_reflns_av_unetI/netI     0.0065
_diffrn_reflns_number            71383
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -50
_diffrn_reflns_limit_l_max       50
_diffrn_reflns_theta_min         2.874
_diffrn_reflns_theta_max         27.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.988
_reflns_Friedel_coverage         0
_reflns_number_total             5853
_reflns_number_gt                5717
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2016)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker 2016)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'Ortep for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2006)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     'dual - dual-space method e.g. SHELXD'
_atom_sites_solution_secondary   'dual - dual-space method e.g. SHELXD'
_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0452P)²+1.1004P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5853
_refine_ls_number_parameters     371
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0372
_refine_ls_wR_factor_ref         0.0991
_refine_ls_wR_factor_gt          0.0987
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.038

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'

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 1.06436(13) 0.11314(16) 0.68147(3) 0.0243(2) Uani 1 1 d . . . . .
C2 C 1.12862(13) 0.06071(16) 0.65115(3) 0.0247(2) Uani 1 1 d . . . . .
H2 H 1.232776 0.034599 0.650946 0.03 Uiso 1 1 calc R U . . .
C3 C 1.03232(13) 0.04853(15) 0.62116(3) 0.0237(2) Uani 1 1 d . . . . .
C4 C 0.88026(13) 0.08168(16) 0.62053(3) 0.0244(2) Uani 1 1 d . . . . .
H4 H 0.817025 0.070318 0.59949 0.029 Uiso 1 1 calc R U . . .
C5 C 0.82393(13) 0.13217(15) 0.65187(3) 0.0230(2) Uani 1 1 d . . . . .
C6 C 0.91339(13) 0.15143(16) 0.68281(3) 0.0238(2) Uani 1 1 d . . . . .
H6 H 0.872971 0.189204 0.703991 0.029 Uiso 1 1 calc R U . . .
N1 N 1.16231(13) 0.12773(18) 0.71412(3) 0.0361(3) Uani 1 1 d . . . . .
N2 N 1.09707(14) -0.00028(16) 0.58805(3) 0.0328(2) Uani 1 1 d . . . . .
N3 N 0.66135(12) 0.16193(15) 0.65249(3) 0.0298(2) Uani 1 1 d . . . . .
O1 O 1.10712(14) 0.1836(2) 0.74023(3) 0.0589(4) Uani 1 1 d . . . . .
O2 O 1.29342(12) 0.0826(2) 0.71300(3) 0.0629(4) Uani 1 1 d . . . . .
O3 O 1.22647(13) -0.05534(17) 0.58947(3) 0.0480(3) Uani 1 1 d . . . . .
O4 O 1.01744(13) 0.02189(17) 0.56081(2) 0.0465(3) Uani 1 1 d . . . . .
O5 O 0.58057(11) 0.09819(14) 0.62810(3) 0.0399(2) Uani 1 1 d . . . . .
O6 O 0.61747(11) 0.24617(16) 0.67757(3) 0.0416(2) Uani 1 1 d . . . . .
C7 C 0.76543(11) 0.59375(15) 0.60383(3) 0.0181(2) Uani 1 1 d . . . . .
C8 C 0.87983(11) 0.60202(14) 0.63486(3) 0.0176(2) Uani 1 1 d . . . . .
C9 C 1.02842(12) 0.55177(15) 0.63011(3) 0.0202(2) Uani 1 1 d . . . . .
C10 C 1.07473(13) 0.49281(16) 0.59680(3) 0.0256(2) Uani 1 1 d . . . . .
H10 H 1.003823 0.488118 0.576985 0.031 Uiso 1 1 calc R U . . .
C11 C 1.22010(15) 0.44336(18) 0.59338(4) 0.0353(3) Uani 1 1 d . . . . .
H11 H 1.249469 0.404973 0.571101 0.042 Uiso 1 1 calc R U . . .
C12 C 1.32799(14) 0.4482(2) 0.62242(5) 0.0419(4) Uani 1 1 d . . . . .
H12 H 1.428667 0.412627 0.619491 0.05 Uiso 1 1 calc R U . . .
C13 C 1.28880(14) 0.5031(2) 0.65434(4) 0.0379(3) Uani 1 1 d . . . . .
H13 H 1.362533 0.505231 0.67361 0.045 Uiso 1 1 calc R U . . .
C14 C 1.13803(12) 0.55810(16) 0.65962(3) 0.0262(2) Uani 1 1 d . . . . .
C15 C 1.09496(14) 0.61728(17) 0.69206(3) 0.0298(3) Uani 1 1 d . . . . .
H15 H 1.167554 0.620935 0.711552 0.036 Uiso 1 1 calc R U . . .
C16 C 0.94789(14) 0.67138(16) 0.69667(3) 0.0251(2) Uani 1 1 d . . . . .
C17 C 0.90527(18) 0.74493(18) 0.72927(3) 0.0350(3) Uani 1 1 d . . . . .
H17 H 0.977295 0.751403 0.748852 0.042 Uiso 1 1 calc R U . . .
C18 C 0.76372(19) 0.80538(19) 0.73257(3) 0.0378(3) Uani 1 1 d . . . . .
H18 H 0.738783 0.858417 0.75416 0.045 Uiso 1 1 calc R U . . .
C19 C 0.65174(16) 0.79075(18) 0.70423(3) 0.0333(3) Uani 1 1 d . . . . .
H19 H 0.552204 0.830801 0.707229 0.04 Uiso 1 1 calc R U . . .
C20 C 0.68651(13) 0.71941(16) 0.67272(3) 0.0247(2) Uani 1 1 d . . . . .
H20 H 0.610453 0.708171 0.654072 0.03 Uiso 1 1 calc R U . . .
C21 C 0.83628(12) 0.66145(14) 0.66753(3) 0.0194(2) Uani 1 1 d . . . . .
O7 O 0.77413(11) 0.73231(12) 0.58230(2) 0.0309(2) Uani 1 1 d . . . . .
H7 H 0.70878 0.720245 0.565455 0.046 Uiso 0.69(3) 1 calc R U P A 2
O8 O 0.67639(10) 0.46710(13) 0.59996(2) 0.0297(2) Uani 1 1 d . . . . .
C22 C 0.64709(12) 0.80598(15) 0.49856(3) 0.0208(2) Uani 1 1 d . . . . .
C23 C 0.55254(14) 0.82336(16) 0.46744(3) 0.0251(2) Uani 1 1 d . . . . .
H23 H 0.590646 0.870103 0.446607 0.03 Uiso 1 1 calc R U . . .
C24 C 0.40524(14) 0.77198(17) 0.46766(3) 0.0278(2) Uani 1 1 d . . . . .
H24 H 0.34021 0.781631 0.446877 0.033 Uiso 1 1 calc R U . . .
C25 C 0.35125(13) 0.70547(16) 0.49853(3) 0.0253(2) Uani 1 1 d . . . . .
C26 C 0.44756(13) 0.69077(15) 0.52808(3) 0.0236(2) Uani 1 1 d . . . . .
H26 H 0.410987 0.645416 0.549185 0.028 Uiso 1 1 calc R U . . .
N4 N 0.59287(10) 0.73928(13) 0.52780(2) 0.02100(19) Uani 1 1 d . . . . .
H4A H 0.652879 0.727056 0.547025 0.025 Uiso 0.31(3) 1 calc R U P A 1
N5 N 0.79389(12) 0.85348(16) 0.50014(3) 0.0303(2) Uani 1 1 d . . . . .
Cl1 Cl 0.16421(3) 0.64352(5) 0.49965(2) 0.04180(11) Uani 1 1 d . . . . .
H5A H 0.847(2) 0.850(3) 0.5206(5) 0.047(5) Uiso 1 1 d . . . . .
H5B H 0.829(2) 0.905(3) 0.4827(5) 0.050(5) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C6 1.3815(16) . ?
C1 C2 1.3826(16) . ?
C1 N1 1.4720(15) . ?
C2 C3 1.3822(16) . ?
C2 H2 0.95 . ?
C3 C4 1.3779(17) . ?
C3 N2 1.4714(14) . ?
C4 C5 1.3813(16) . ?
C4 H4 0.95 . ?
C5 C6 1.3823(16) . ?
C5 N3 1.4702(15) . ?
C6 H6 0.95 . ?
N1 O1 1.2134(16) . ?
N1 O2 1.2197(17) . ?
N2 O3 1.2197(17) . ?
N2 O4 1.2257(16) . ?
N3 O6 1.2231(15) . ?
N3 O5 1.2238(15) . ?
C7 O8 1.2131(13) . ?
C7 O7 1.2999(13) . ?
C7 C8 1.5062(14) . ?
C8 C9 1.4010(14) . ?
C8 C21 1.4011(14) . ?
C9 C10 1.4310(16) . ?
C9 C14 1.4367(15) . ?
C10 C11 1.3625(17) . ?
C10 H10 0.95 . ?
C11 C12 1.414(2) . ?
C11 H11 0.95 . ?
C12 C13 1.352(2) . ?
C12 H12 0.95 . ?
C13 C14 1.4329(17) . ?
C13 H13 0.95 . ?
C14 C15 1.3911(19) . ?
C15 C16 1.3944(18) . ?
C15 H15 0.95 . ?
C16 C17 1.4304(17) . ?
C16 C21 1.4390(15) . ?
C17 C18 1.352(2) . ?
C17 H17 0.95 . ?
C18 C19 1.421(2) . ?
C18 H18 0.95 . ?
C19 C20 1.3654(17) . ?
C19 H19 0.95 . ?
C20 C21 1.4299(15) . ?
C20 H20 0.95 . ?
O7 H7 0.84 . ?
C22 N4 1.3393(14) . ?
C22 N5 1.3525(15) . ?
C22 C23 1.4105(15) . ?
C23 C24 1.3678(18) . ?
C23 H23 0.95 . ?
C24 C25 1.3918(18) . ?
C24 H24 0.95 . ?
C25 C26 1.3702(16) . ?
C25 Cl1 1.7334(12) . ?
C26 N4 1.3453(15) . ?
C26 H26 0.95 . ?
N4 H4A 0.88 . ?
N5 H5A 0.89(2) . ?
N5 H5B 0.84(2) . ?

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
C6 C1 C2 123.62(10) . . ?
C6 C1 N1 118.31(10) . . ?
C2 C1 N1 118.07(11) . . ?
C3 C2 C1 116.03(11) . . ?
C3 C2 H2 122 . . ?
C1 C2 H2 122 . . ?
C4 C3 C2 123.70(10) . . ?
C4 C3 N2 118.51(10) . . ?
C2 C3 N2 117.78(11) . . ?
C3 C4 C5 116.98(10) . . ?
C3 C4 H4 121.5 . . ?
C5 C4 H4 121.5 . . ?
C4 C5 C6 122.79(11) . . ?
C4 C5 N3 118.49(10) . . ?
C6 C5 N3 118.70(10) . . ?
C1 C6 C5 116.86(10) . . ?
C1 C6 H6 121.6 . . ?
C5 C6 H6 121.6 . . ?
O1 N1 O2 124.62(12) . . ?
O1 N1 C1 117.82(11) . . ?
O2 N1 C1 117.56(11) . . ?
O3 N2 O4 124.60(11) . . ?
O3 N2 C3 118.19(11) . . ?
O4 N2 C3 117.19(12) . . ?
O6 N3 O5 125.22(11) . . ?
O6 N3 C5 117.40(11) . . ?
O5 N3 C5 117.38(11) . . ?
O8 C7 O7 124.86(10) . . ?
O8 C7 C8 121.72(10) . . ?
O7 C7 C8 113.41(9) . . ?
C9 C8 C21 121.57(10) . . ?
C9 C8 C7 118.79(9) . . ?
C21 C8 C7 119.63(9) . . ?
C8 C9 C10 122.14(10) . . ?
C8 C9 C14 119.14(10) . . ?
C10 C9 C14 118.72(10) . . ?
C11 C10 C9 120.28(12) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 121.14(13) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C13 C12 C11 120.42(12) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 121.18(13) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
C15 C14 C13 122.41(12) . . ?
C15 C14 C9 119.33(10) . . ?
C13 C14 C9 118.26(12) . . ?
C14 C15 C16 121.64(10) . . ?
C14 C15 H15 119.2 . . ?
C16 C15 H15 119.2 . . ?
C15 C16 C17 121.92(11) . . ?
C15 C16 C21 119.54(10) . . ?
C17 C16 C21 118.48(11) . . ?
C18 C17 C16 120.84(12) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C17 C18 C19 120.99(12) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 H18 119.5 . . ?
C20 C19 C18 120.32(12) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C19 C20 C21 120.65(12) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
C8 C21 C20 122.57(10) . . ?
C8 C21 C16 118.73(10) . . ?
C20 C21 C16 118.65(10) . . ?
C7 O7 H7 109.5 . . ?
N4 C22 N5 117.65(10) . . ?
N4 C22 C23 120.18(10) . . ?
N5 C22 C23 122.16(11) . . ?
C24 C23 C22 119.09(11) . . ?
C24 C23 H23 120.5 . . ?
C22 C23 H23 120.5 . . ?
C23 C24 C25 119.57(10) . . ?
C23 C24 H24 120.2 . . ?
C25 C24 H24 120.2 . . ?
C26 C25 C24 119.17(11) . . ?
C26 C25 Cl1 120.44(10) . . ?
C24 C25 Cl1 120.39(9) . . ?
N4 C26 C25 121.34(10) . . ?
N4 C26 H26 119.3 . . ?
C25 C26 H26 119.3 . . ?
C22 N4 C26 120.64(10) . . ?
C22 N4 H4A 119.7 . . ?
C26 N4 H4A 119.7 . . ?
C22 N5 H5A 119.1(12) . . ?
C22 N5 H5B 119.6(13) . . ?
H5A N5 H5B 120.3(18) . . ?

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
C6 C1 C2 C3 0.28(18) . . . . ?
N1 C1 C2 C3 179.88(11) . . . . ?
C1 C2 C3 C4 -1.33(17) . . . . ?
C1 C2 C3 N2 177.84(10) . . . . ?
C2 C3 C4 C5 0.92(17) . . . . ?
N2 C3 C4 C5 -178.25(10) . . . . ?
C3 C4 C5 C6 0.60(17) . . . . ?
C3 C4 C5 N3 -177.77(10) . . . . ?
C2 C1 C6 C5 1.09(18) . . . . ?
N1 C1 C6 C5 -178.51(10) . . . . ?
C4 C5 C6 C1 -1.55(17) . . . . ?
N3 C5 C6 C1 176.82(10) . . . . ?
C6 C1 N1 O1 -4.34(19) . . . . ?
C2 C1 N1 O1 176.03(14) . . . . ?
C6 C1 N1 O2 175.59(14) . . . . ?
C2 C1 N1 O2 -4.03(19) . . . . ?
C4 C3 N2 O3 -169.60(11) . . . . ?
C2 C3 N2 O3 11.18(17) . . . . ?
C4 C3 N2 O4 12.14(16) . . . . ?
C2 C3 N2 O4 -167.08(11) . . . . ?
C4 C5 N3 O6 -163.61(11) . . . . ?
C6 C5 N3 O6 17.95(16) . . . . ?
C4 C5 N3 O5 17.37(16) . . . . ?
C6 C5 N3 O5 -161.07(11) . . . . ?
O8 C7 C8 C9 102.01(12) . . . . ?
O7 C7 C8 C9 -77.32(12) . . . . ?
O8 C7 C8 C21 -78.74(14) . . . . ?
O7 C7 C8 C21 101.93(11) . . . . ?
C21 C8 C9 C10 -179.30(10) . . . . ?
C7 C8 C9 C10 -0.07(15) . . . . ?
C21 C8 C9 C14 1.18(16) . . . . ?
C7 C8 C9 C14 -179.59(9) . . . . ?
C8 C9 C10 C11 -179.35(11) . . . . ?
C14 C9 C10 C11 0.18(16) . . . . ?
C9 C10 C11 C12 0.27(18) . . . . ?
C10 C11 C12 C13 -0.3(2) . . . . ?
C11 C12 C13 C14 -0.2(2) . . . . ?
C12 C13 C14 C15 -179.22(12) . . . . ?
C12 C13 C14 C9 0.61(19) . . . . ?
C8 C9 C14 C15 -1.23(16) . . . . ?
C10 C9 C14 C15 179.23(11) . . . . ?
C8 C9 C14 C13 178.94(11) . . . . ?
C10 C9 C14 C13 -0.60(16) . . . . ?
C13 C14 C15 C16 179.61(12) . . . . ?
C9 C14 C15 C16 -0.22(18) . . . . ?
C14 C15 C16 C17 -175.41(11) . . . . ?
C14 C15 C16 C21 1.70(18) . . . . ?
C15 C16 C17 C18 176.55(12) . . . . ?
C21 C16 C17 C18 -0.59(18) . . . . ?
C16 C17 C18 C19 2.6(2) . . . . ?
C17 C18 C19 C20 -1.7(2) . . . . ?
C18 C19 C20 C21 -1.11(18) . . . . ?
C9 C8 C21 C20 177.82(10) . . . . ?
C7 C8 C21 C20 -1.40(16) . . . . ?
C9 C8 C21 C16 0.28(15) . . . . ?
C7 C8 C21 C16 -178.94(9) . . . . ?
C19 C20 C21 C8 -174.54(11) . . . . ?
C19 C20 C21 C16 3.00(16) . . . . ?
C15 C16 C21 C8 -1.72(16) . . . . ?
C17 C16 C21 C8 175.49(10) . . . . ?
C15 C16 C21 C20 -179.35(11) . . . . ?
C17 C16 C21 C20 -2.14(16) . . . . ?
N4 C22 C23 C24 0.27(17) . . . . ?
N5 C22 C23 C24 179.73(11) . . . . ?
C22 C23 C24 C25 0.61(17) . . . . ?
C23 C24 C25 C26 -0.74(18) . . . . ?
C23 C24 C25 Cl1 178.82(9) . . . . ?
C24 C25 C26 N4 0.00(18) . . . . ?
Cl1 C25 C26 N4 -179.57(9) . . . . ?
N5 C22 N4 C26 179.49(10) . . . . ?
C23 C22 N4 C26 -1.03(16) . . . . ?
C25 C26 N4 C22 0.90(17) . . . . ?

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
O7 H7^b N4 0.84 1.71 2.5390(12) 167 . yes
N4 H4A^a O7 0.88 1.66 2.5390(12) 172 . yes
N5 H5A O4 0.89(2) 2.42(2) 3.1831(16) 145(2) 1_565 yes
N5 H5B O4 0.84(2) 2.30(2) 3.1065(15) 162(2) 3_766 yes



# END of CIF
####################################################################### 
# 
# 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_Form_I
_database_code_depnum_ccdc_archive 'CCDC 2157390'
_audit_update_record             
;
2022-06-22 deposited with the CCDC.	2022-07-18 downloaded from the CCDC.
;

_audit_creation_date             2022-06-21T11:13:14-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C15 H9 O2, C6 H3 N3 O6, C5 H6 Cl N2'
_chemical_formula_sum            'C26 H18 Cl N5 O8'
_chemical_formula_weight         563.9

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.1140(2)
_cell_length_b                   9.7490(3)
_cell_length_c                   18.0972(5)
_cell_angle_alpha                88.738(2)
_cell_angle_beta                 81.565(2)
_cell_angle_gamma                89.703(2)
_cell_volume                     1241.24(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9516
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      27.73
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.495
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.098
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             580
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2 -1 1 0.243
-4 3 -2 0.205
0 0 -1 0.046
0 0 1 0.059
-3 1 2 0.2
1 0 -1 0.211
2 0 -1 0.228
-3 -1 0 0.207
1 0 1 0.244
0 3 1 0.046
0 1 -2 0.057
0 -1 2 0.078
-1 -3 -2 0.102
0 -1 -1 0.047
0 -2 -1 0.057
0 1 1 0.049
-1 0 3 0.133
-1 -4 3 0.071

_exptl_special_details           
;
 Absorption corrections were made using the program SADABS
        (Sheldrick, 1996)
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.217
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_correction_T_min  0.7108
_exptl_absorpt_correction_T_max  0.7457
_shelx_estimated_absorpt_T_min   0.9
_shelx_estimated_absorpt_T_max   0.979

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'Bruker D8 Venture Photon CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.039
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_number            47374
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.089
_diffrn_reflns_theta_max         27.992
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 1
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 1
_reflns_Friedel_coverage         0
_reflns_number_total             5991
_reflns_number_gt                4379
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2016)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker 2016)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'Ortep for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2006)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     'dual - dual-space method e.g. SHELXD'
_atom_sites_solution_secondary   'dual - dual-space method e.g. SHELXD'
_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0490P)²+0.3487P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5991
_refine_ls_number_parameters     367
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_ref         0.1109
_refine_ls_wR_factor_gt          0.1006
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.29
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.047

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'

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 0.8273(2) 0.52668(15) 0.16876(8) 0.0227(3) Uani 1 1 d . . . . .
C2 C 0.8052(2) 0.53684(16) 0.24551(9) 0.0257(3) Uani 1 1 d . . . . .
H2 H 0.830106 0.461185 0.276643 0.031 Uiso 1 1 calc R U . . .
C3 C 0.7455(2) 0.66133(17) 0.27497(8) 0.0259(3) Uani 1 1 d . . . . .
C4 C 0.7048(2) 0.77349(16) 0.23170(9) 0.0267(3) Uani 1 1 d . . . . .
H4 H 0.663315 0.858267 0.253427 0.032 Uiso 1 1 calc R U . . .
C5 C 0.7275(2) 0.75596(15) 0.15572(9) 0.0253(3) Uani 1 1 d . . . . .
C6 C 0.7905(2) 0.63455(16) 0.12193(8) 0.0241(3) Uani 1 1 d . . . . .
H6 H 0.807674 0.625828 0.069187 0.029 Uiso 1 1 calc R U . . .
N1 N 0.89350(18) 0.39538(13) 0.13515(8) 0.0287(3) Uani 1 1 d . . . . .
N2 N 0.72863(19) 0.67710(17) 0.35630(8) 0.0353(3) Uani 1 1 d . . . . .
N3 N 0.6851(2) 0.87260(14) 0.10750(9) 0.0344(3) Uani 1 1 d . . . . .
O1 O 0.91763(18) 0.38811(13) 0.06718(7) 0.0401(3) Uani 1 1 d . . . . .
O2 O 0.92090(19) 0.30073(12) 0.17782(7) 0.0425(3) Uani 1 1 d . . . . .
O3 O 0.69395(19) 0.57481(15) 0.39613(7) 0.0468(3) Uani 1 1 d . . . . .
O4 O 0.75221(18) 0.79269(15) 0.37861(7) 0.0463(3) Uani 1 1 d . . . . .
O5 O 0.6377(2) 0.98046(13) 0.13830(8) 0.0521(4) Uani 1 1 d . . . . .
O6 O 0.6999(2) 0.85447(14) 0.04066(7) 0.0491(4) Uani 1 1 d . . . . .
C7 C 0.2348(2) 0.63604(15) 0.33027(8) 0.0226(3) Uani 1 1 d . . . . .
C8 C 0.25553(19) 0.63814(14) 0.24604(8) 0.0189(3) Uani 1 1 d . . . . .
C9 C 0.31445(19) 0.51818(14) 0.20659(8) 0.0188(3) Uani 1 1 d . . . . .
C10 C 0.3661(2) 0.39398(15) 0.24223(8) 0.0240(3) Uani 1 1 d . . . . .
H10 H 0.360796 0.390079 0.294991 0.029 Uiso 1 1 calc R U . . .
C11 C 0.4229(2) 0.28111(16) 0.20152(9) 0.0283(3) Uani 1 1 d . . . . .
H11 H 0.457355 0.199989 0.22636 0.034 Uiso 1 1 calc R U . . .
C12 C 0.4312(2) 0.28284(16) 0.12272(9) 0.0295(4) Uani 1 1 d . . . . .
H12 H 0.46968 0.203062 0.095213 0.035 Uiso 1 1 calc R U . . .
C13 C 0.3843(2) 0.39834(15) 0.08686(8) 0.0251(3) Uani 1 1 d . . . . .
H13 H 0.389747 0.398495 0.03409 0.03 Uiso 1 1 calc R U . . .
C14 C 0.32681(19) 0.52021(14) 0.12659(8) 0.0200(3) Uani 1 1 d . . . . .
C15 C 0.2818(2) 0.63979(15) 0.08954(8) 0.0215(3) Uani 1 1 d . . . . .
H15 H 0.289172 0.639995 0.036699 0.026 Uiso 1 1 calc R U . . .
C16 C 0.22614(19) 0.75930(15) 0.12777(8) 0.0209(3) Uani 1 1 d . . . . .
C17 C 0.1808(2) 0.88146(16) 0.08870(9) 0.0264(3) Uani 1 1 d . . . . .
H17 H 0.190532 0.881834 0.03578 0.032 Uiso 1 1 calc R U . . .
C18 C 0.1240(2) 0.99700(16) 0.12653(9) 0.0303(4) Uani 1 1 d . . . . .
H18 H 0.095409 1.077864 0.100057 0.036 Uiso 1 1 calc R U . . .
C19 C 0.1074(2) 0.99650(16) 0.20547(9) 0.0287(3) Uani 1 1 d . . . . .
H19 H 0.066378 1.077438 0.231449 0.034 Uiso 1 1 calc R U . . .
C20 C 0.1489(2) 0.88295(15) 0.24492(9) 0.0243(3) Uani 1 1 d . . . . .
H20 H 0.135985 0.885673 0.297865 0.029 Uiso 1 1 calc R U . . .
C21 C 0.21196(19) 0.75897(14) 0.20765(8) 0.0198(3) Uani 1 1 d . . . . .
O7 O 0.33819(15) 0.71974(12) 0.35888(6) 0.0302(3) Uani 1 1 d . . . . .
O8 O 0.11800(16) 0.55624(12) 0.36629(6) 0.0325(3) Uani 1 1 d . . . . .
C22 C 0.1268(2) 0.72193(16) 0.54670(8) 0.0268(3) Uani 1 1 d . . . . .
C23 C 0.1121(2) 0.75496(17) 0.62297(9) 0.0301(4) Uani 1 1 d . . . . .
H23 H 0.000829 0.731314 0.656487 0.036 Uiso 1 1 calc R U . . .
C24 C 0.2575(2) 0.82066(17) 0.64830(9) 0.0313(4) Uani 1 1 d . . . . .
H24 H 0.24781 0.843769 0.699447 0.038 Uiso 1 1 calc R U . . .
C25 C 0.4216(2) 0.85408(17) 0.59855(9) 0.0309(4) Uani 1 1 d . . . . .
C26 C 0.4324(2) 0.82098(17) 0.52570(9) 0.0326(4) Uani 1 1 d . . . . .
H26 H 0.543383 0.843372 0.491733 0.039 Uiso 1 1 calc R U . . .
N4 N 0.2869(2) 0.75650(13) 0.50096(7) 0.0293(3) Uani 1 1 d . . . . .
H4A H 0.297069 0.736406 0.453368 0.035 Uiso 1 1 calc R U . . .
N5 N -0.0128(2) 0.66121(16) 0.51782(9) 0.0363(4) Uani 1 1 d . . . . .
Cl1 Cl 0.60717(7) 0.93964(5) 0.62901(3) 0.04844(15) Uani 1 1 d . . . . .
H5A H 0.013(3) 0.634(2) 0.4708(13) 0.058 Uiso 1 1 d . U . . .
H5B H -0.101(3) 0.619(2) 0.5514(12) 0.058 Uiso 1 1 d . U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C2 1.380(2) . ?
C1 C6 1.384(2) . ?
C1 N1 1.4745(19) . ?
C2 C3 1.376(2) . ?
C2 H2 0.95 . ?
C3 C4 1.385(2) . ?
C3 N2 1.470(2) . ?
C4 C5 1.375(2) . ?
C4 H4 0.95 . ?
C5 C6 1.386(2) . ?
C5 N3 1.475(2) . ?
C6 H6 0.95 . ?
N1 O1 1.2204(17) . ?
N1 O2 1.2235(17) . ?
N2 O3 1.2222(19) . ?
N2 O4 1.2260(19) . ?
N3 O6 1.2154(19) . ?
N3 O5 1.2236(19) . ?
C7 O8 1.2433(18) . ?
C7 O7 1.2695(18) . ?
C7 C8 1.5095(19) . ?
C8 C21 1.410(2) . ?
C8 C9 1.4132(19) . ?
C9 C10 1.431(2) . ?
C9 C14 1.4371(19) . ?
C10 C11 1.364(2) . ?
C10 H10 0.95 . ?
C11 C12 1.418(2) . ?
C11 H11 0.95 . ?
C12 C13 1.352(2) . ?
C12 H12 0.95 . ?
C13 C14 1.429(2) . ?
C13 H13 0.95 . ?
C14 C15 1.391(2) . ?
C15 C16 1.394(2) . ?
C15 H15 0.95 . ?
C16 C17 1.431(2) . ?
C16 C21 1.434(2) . ?
C17 C18 1.360(2) . ?
C17 H17 0.95 . ?
C18 C19 1.416(2) . ?
C18 H18 0.95 . ?
C19 C20 1.359(2) . ?
C19 H19 0.95 . ?
C20 C21 1.435(2) . ?
C20 H20 0.95 . ?
C22 N5 1.335(2) . ?
C22 N4 1.346(2) . ?
C22 C23 1.413(2) . ?
C23 C24 1.360(2) . ?
C23 H23 0.95 . ?
C24 C25 1.401(2) . ?
C24 H24 0.95 . ?
C25 C26 1.355(2) . ?
C25 Cl1 1.7283(17) . ?
C26 N4 1.350(2) . ?
C26 H26 0.95 . ?
N4 H4A 0.88 . ?
N5 H5A 0.89(2) . ?
N5 H5B 0.90(2) . ?

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
C2 C1 C6 122.85(14) . . ?
C2 C1 N1 118.61(13) . . ?
C6 C1 N1 118.54(13) . . ?
C3 C2 C1 117.11(14) . . ?
C3 C2 H2 121.4 . . ?
C1 C2 H2 121.4 . . ?
C2 C3 C4 123.30(14) . . ?
C2 C3 N2 118.36(14) . . ?
C4 C3 N2 118.32(14) . . ?
C5 C4 C3 116.64(14) . . ?
C5 C4 H4 121.7 . . ?
C3 C4 H4 121.7 . . ?
C4 C5 C6 123.32(14) . . ?
C4 C5 N3 118.49(14) . . ?
C6 C5 N3 118.19(14) . . ?
C1 C6 C5 116.77(14) . . ?
C1 C6 H6 121.6 . . ?
C5 C6 H6 121.6 . . ?
O1 N1 O2 124.41(14) . . ?
O1 N1 C1 118.33(13) . . ?
O2 N1 C1 117.26(13) . . ?
O3 N2 O4 125.23(15) . . ?
O3 N2 C3 117.93(15) . . ?
O4 N2 C3 116.84(15) . . ?
O6 N3 O5 125.15(15) . . ?
O6 N3 C5 117.84(14) . . ?
O5 N3 C5 117.01(15) . . ?
O8 C7 O7 124.98(13) . . ?
O8 C7 C8 118.88(13) . . ?
O7 C7 C8 116.12(12) . . ?
C21 C8 C9 120.71(12) . . ?
C21 C8 C7 119.63(12) . . ?
C9 C8 C7 119.65(12) . . ?
C8 C9 C10 123.24(13) . . ?
C8 C9 C14 119.03(13) . . ?
C10 C9 C14 117.72(13) . . ?
C11 C10 C9 120.94(14) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C10 C11 C12 121.10(14) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C13 C12 C11 119.82(14) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C14 121.44(14) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 H13 119.3 . . ?
C15 C14 C13 121.43(13) . . ?
C15 C14 C9 119.61(13) . . ?
C13 C14 C9 118.96(13) . . ?
C14 C15 C16 121.86(13) . . ?
C14 C15 H15 119.1 . . ?
C16 C15 H15 119.1 . . ?
C15 C16 C17 121.09(13) . . ?
C15 C16 C21 119.31(13) . . ?
C17 C16 C21 119.60(13) . . ?
C18 C17 C16 120.70(14) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C17 C18 C19 119.84(14) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
C20 C19 C18 121.52(14) . . ?
C20 C19 H19 119.2 . . ?
C18 C19 H19 119.2 . . ?
C19 C20 C21 120.86(14) . . ?
C19 C20 H20 119.6 . . ?
C21 C20 H20 119.6 . . ?
C8 C21 C16 119.47(13) . . ?
C8 C21 C20 123.05(13) . . ?
C16 C21 C20 117.46(13) . . ?
N5 C22 N4 118.72(14) . . ?
N5 C22 C23 122.88(15) . . ?
N4 C22 C23 118.38(14) . . ?
C24 C23 C22 119.88(15) . . ?
C24 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C23 C24 C25 119.63(15) . . ?
C23 C24 H24 120.2 . . ?
C25 C24 H24 120.2 . . ?
C26 C25 C24 119.34(15) . . ?
C26 C25 Cl1 120.08(13) . . ?
C24 C25 Cl1 120.57(12) . . ?
N4 C26 C25 120.63(15) . . ?
N4 C26 H26 119.7 . . ?
C25 C26 H26 119.7 . . ?
C22 N4 C26 122.15(13) . . ?
C22 N4 H4A 118.9 . . ?
C26 N4 H4A 118.9 . . ?
C22 N5 H5A 117.4(14) . . ?
C22 N5 H5B 115.2(14) . . ?
H5A N5 H5B 121.9(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
C6 C1 C2 C3 -0.6(2) . . . . ?
N1 C1 C2 C3 179.19(13) . . . . ?
C1 C2 C3 C4 1.0(2) . . . . ?
C1 C2 C3 N2 -177.40(13) . . . . ?
C2 C3 C4 C5 -0.3(2) . . . . ?
N2 C3 C4 C5 178.19(13) . . . . ?
C3 C4 C5 C6 -1.0(2) . . . . ?
C3 C4 C5 N3 179.82(13) . . . . ?
C2 C1 C6 C5 -0.6(2) . . . . ?
N1 C1 C6 C5 179.63(13) . . . . ?
C4 C5 C6 C1 1.4(2) . . . . ?
N3 C5 C6 C1 -179.41(12) . . . . ?
C2 C1 N1 O1 -178.07(13) . . . . ?
C6 C1 N1 O1 1.7(2) . . . . ?
C2 C1 N1 O2 1.8(2) . . . . ?
C6 C1 N1 O2 -178.40(13) . . . . ?
C2 C3 N2 O3 -28.3(2) . . . . ?
C4 C3 N2 O3 153.18(14) . . . . ?
C2 C3 N2 O4 151.15(14) . . . . ?
C4 C3 N2 O4 -27.4(2) . . . . ?
C4 C5 N3 O6 -177.69(14) . . . . ?
C6 C5 N3 O6 3.1(2) . . . . ?
C4 C5 N3 O5 2.3(2) . . . . ?
C6 C5 N3 O5 -176.88(14) . . . . ?
O8 C7 C8 C21 117.34(15) . . . . ?
O7 C7 C8 C21 -61.41(18) . . . . ?
O8 C7 C8 C9 -61.30(19) . . . . ?
O7 C7 C8 C9 119.95(15) . . . . ?
C21 C8 C9 C10 178.02(13) . . . . ?
C7 C8 C9 C10 -3.4(2) . . . . ?
C21 C8 C9 C14 -0.91(19) . . . . ?
C7 C8 C9 C14 177.72(12) . . . . ?
C8 C9 C10 C11 -179.71(14) . . . . ?
C14 C9 C10 C11 -0.8(2) . . . . ?
C9 C10 C11 C12 -0.5(2) . . . . ?
C10 C11 C12 C13 0.7(2) . . . . ?
C11 C12 C13 C14 0.3(2) . . . . ?
C12 C13 C14 C15 178.85(14) . . . . ?
C12 C13 C14 C9 -1.5(2) . . . . ?
C8 C9 C14 C15 0.3(2) . . . . ?
C10 C9 C14 C15 -178.65(13) . . . . ?
C8 C9 C14 C13 -179.29(12) . . . . ?
C10 C9 C14 C13 1.72(19) . . . . ?
C13 C14 C15 C16 -179.79(13) . . . . ?
C9 C14 C15 C16 0.6(2) . . . . ?
C14 C15 C16 C17 179.84(13) . . . . ?
C14 C15 C16 C21 -0.9(2) . . . . ?
C15 C16 C17 C18 179.03(14) . . . . ?
C21 C16 C17 C18 -0.2(2) . . . . ?
C16 C17 C18 C19 -0.6(2) . . . . ?
C17 C18 C19 C20 0.6(2) . . . . ?
C18 C19 C20 C21 0.2(2) . . . . ?
C9 C8 C21 C16 0.56(19) . . . . ?
C7 C8 C21 C16 -178.06(12) . . . . ?
C9 C8 C21 C20 179.07(13) . . . . ?
C7 C8 C21 C20 0.4(2) . . . . ?
C15 C16 C21 C8 0.4(2) . . . . ?
C17 C16 C21 C8 179.58(13) . . . . ?
C15 C16 C21 C20 -178.24(13) . . . . ?
C17 C16 C21 C20 0.99(19) . . . . ?
C19 C20 C21 C8 -179.55(14) . . . . ?
C19 C20 C21 C16 -1.0(2) . . . . ?
N5 C22 C23 C24 -177.96(16) . . . . ?
N4 C22 C23 C24 0.3(2) . . . . ?
C22 C23 C24 C25 -0.5(2) . . . . ?
C23 C24 C25 C26 0.4(3) . . . . ?
C23 C24 C25 Cl1 179.11(13) . . . . ?
C24 C25 C26 N4 0.0(3) . . . . ?
Cl1 C25 C26 N4 -178.72(13) . . . . ?
N5 C22 N4 C26 178.44(15) . . . . ?
C23 C22 N4 C26 0.1(2) . . . . ?
C25 C26 N4 C22 -0.3(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
N5 H5B O8 0.90(2) 2.23(2) 2.9687(19) 138(2) 2_566 yes
N4 H4A O7 0.88 1.7 2.5762(16) 171 . yes



# END of CIF
####################################################################### 
# 
# 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_Form_II
_database_code_depnum_ccdc_archive 'CCDC 2157391'
_audit_update_record             
;
2022-06-22 deposited with the CCDC.	2022-07-18 downloaded from the CCDC.
;

_audit_creation_date             2022-06-21T11:52:55-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C15 H10 O2, C6 H3 N3 O6, C5 H5 Cl N2'
_chemical_formula_sum            'C26 H18 Cl N5 O8'
_chemical_formula_weight         563.9

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.9341(5)
_cell_length_b                   7.2129(4)
_cell_length_c                   38.172(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.311(2)
_cell_angle_gamma                90
_cell_volume                     2452.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    9839
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      36.49
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       cube
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.404
_exptl_crystal_size_mid          0.291
_exptl_crystal_size_min          0.276
_exptl_crystal_density_diffrn    1.527
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1160
_exptl_special_details           
;
 Absorption corrections were made using the program SADABS
        (Sheldrick, 1996)
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.22
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_correction_T_min  0.7007
_exptl_absorpt_correction_T_max  0.7471
_shelx_estimated_absorpt_T_min   0.917
_shelx_estimated_absorpt_T_max   0.942

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'Bruker D8 Venture Photon CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.014
_diffrn_reflns_av_unetI/netI     0.0065
_diffrn_reflns_number            71399
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -50
_diffrn_reflns_limit_l_max       50
_diffrn_reflns_theta_min         2.874
_diffrn_reflns_theta_max         27.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.988
_reflns_Friedel_coverage         0
_reflns_number_total             5853
_reflns_number_gt                5717
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2016)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker 2016)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     'dual - dual-space method e.g. SHELXD'
_atom_sites_solution_secondary   'dual - dual-space method e.g. SHELXD'
_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0463P)²+1.1572P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5853
_refine_ls_number_parameters     370
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0375
_refine_ls_wR_factor_ref         0.1001
_refine_ls_wR_factor_gt          0.0997
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.039

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'

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 1.06428(13) 0.11315(17) 0.68147(3) 0.0243(2) Uani 1 1 d . . . . .
C2 C 1.12864(13) 0.06069(16) 0.65115(3) 0.0246(2) Uani 1 1 d . . . . .
H2 H 1.232795 0.034578 0.650952 0.03 Uiso 1 1 calc R U . . .
C3 C 1.03233(14) 0.04852(16) 0.62115(3) 0.0237(2) Uani 1 1 d . . . . .
C4 C 0.88033(14) 0.08169(16) 0.62052(3) 0.0243(2) Uani 1 1 d . . . . .
H4 H 0.817122 0.070371 0.599475 0.029 Uiso 1 1 calc R U . . .
C5 C 0.82390(13) 0.13217(15) 0.65187(3) 0.0230(2) Uani 1 1 d . . . . .
C6 C 0.91341(13) 0.15141(16) 0.68281(3) 0.0238(2) Uani 1 1 d . . . . .
H6 H 0.872999 0.189175 0.703992 0.029 Uiso 1 1 calc R U . . .
N1 N 1.16232(13) 0.12772(18) 0.71413(3) 0.0361(3) Uani 1 1 d . . . . .
N2 N 1.09704(14) -0.00032(16) 0.58805(3) 0.0327(2) Uani 1 1 d . . . . .
N3 N 0.66131(12) 0.16194(15) 0.65248(3) 0.0298(2) Uani 1 1 d . . . . .
O1 O 1.10716(14) 0.1836(2) 0.74023(3) 0.0588(4) Uani 1 1 d . . . . .
O2 O 1.29344(13) 0.0826(2) 0.71301(3) 0.0628(4) Uani 1 1 d . . . . .
O3 O 1.22652(13) -0.05539(17) 0.58947(3) 0.0479(3) Uani 1 1 d . . . . .
O4 O 1.01743(14) 0.02192(17) 0.56081(2) 0.0463(3) Uani 1 1 d . . . . .
O5 O 0.58048(11) 0.09819(14) 0.62810(3) 0.0399(2) Uani 1 1 d . . . . .
O6 O 0.61746(11) 0.24619(16) 0.67756(3) 0.0416(2) Uani 1 1 d . . . . .
C7 C 0.76541(11) 0.59374(15) 0.60384(3) 0.0181(2) Uani 1 1 d . . . . .
C8 C 0.87987(11) 0.60206(14) 0.63485(3) 0.0176(2) Uani 1 1 d . . . . .
C9 C 1.02839(12) 0.55179(15) 0.63010(3) 0.0202(2) Uani 1 1 d . . . . .
C10 C 1.07473(13) 0.49280(16) 0.59680(3) 0.0255(2) Uani 1 1 d . . . . .
H10 H 1.003831 0.48812 0.576979 0.031 Uiso 1 1 calc R U . . .
C11 C 1.22015(15) 0.44329(18) 0.59338(4) 0.0352(3) Uani 1 1 d . . . . .
H11 H 1.249531 0.404823 0.571105 0.042 Uiso 1 1 calc R U . . .
C12 C 1.32797(14) 0.4482(2) 0.62242(5) 0.0419(4) Uani 1 1 d . . . . .
H12 H 1.428664 0.412717 0.619494 0.05 Uiso 1 1 calc R U . . .
C13 C 1.28882(14) 0.5031(2) 0.65433(4) 0.0379(3) Uani 1 1 d . . . . .
H13 H 1.362572 0.505239 0.673601 0.045 Uiso 1 1 calc R U . . .
C14 C 1.13805(12) 0.55806(16) 0.65961(3) 0.0262(2) Uani 1 1 d . . . . .
C15 C 1.09487(14) 0.61729(18) 0.69207(3) 0.0298(3) Uani 1 1 d . . . . .
H15 H 1.167434 0.620964 0.71157 0.036 Uiso 1 1 calc R U . . .
C16 C 0.94789(14) 0.67134(16) 0.69667(3) 0.0251(2) Uani 1 1 d . . . . .
C17 C 0.90531(18) 0.74490(19) 0.72928(3) 0.0349(3) Uani 1 1 d . . . . .
H17 H 0.977331 0.751359 0.748863 0.042 Uiso 1 1 calc R U . . .
C18 C 0.76362(19) 0.80542(19) 0.73257(3) 0.0378(3) Uani 1 1 d . . . . .
H18 H 0.738646 0.858488 0.754147 0.045 Uiso 1 1 calc R U . . .
C19 C 0.65178(16) 0.79078(18) 0.70424(4) 0.0332(3) Uani 1 1 d . . . . .
H19 H 0.552244 0.830822 0.707237 0.04 Uiso 1 1 calc R U . . .
C20 C 0.68650(13) 0.71946(16) 0.67273(3) 0.0247(2) Uani 1 1 d . . . . .
H20 H 0.610431 0.708268 0.654084 0.03 Uiso 1 1 calc R U . . .
C21 C 0.83625(12) 0.66146(15) 0.66753(3) 0.0194(2) Uani 1 1 d . . . . .
O7 O 0.77425(11) 0.73234(13) 0.58233(2) 0.0309(2) Uani 1 1 d . . . . .
H7 H 0.708366 0.720972 0.565578 0.046 Uiso 1 1 calc R U . . .
O8 O 0.67639(10) 0.46707(13) 0.59995(2) 0.0296(2) Uani 1 1 d . . . . .
C22 C 0.64714(12) 0.80602(15) 0.49856(3) 0.0207(2) Uani 1 1 d . . . . .
C23 C 0.55258(14) 0.82338(16) 0.46744(3) 0.0251(2) Uani 1 1 d . . . . .
H23 H 0.590664 0.870155 0.446606 0.03 Uiso 1 1 calc R U . . .
C24 C 0.40530(14) 0.77194(17) 0.46766(3) 0.0278(2) Uani 1 1 d . . . . .
H24 H 0.340308 0.781533 0.446872 0.033 Uiso 1 1 calc R U . . .
C25 C 0.35119(13) 0.70545(16) 0.49853(3) 0.0252(2) Uani 1 1 d . . . . .
C26 C 0.44758(13) 0.69075(16) 0.52809(3) 0.0236(2) Uani 1 1 d . . . . .
H26 H 0.410982 0.645341 0.549188 0.028 Uiso 1 1 calc R U . . .
N4 N 0.59293(11) 0.73928(13) 0.52784(2) 0.02101(19) Uani 1 1 d . . . . .
N5 N 0.79386(12) 0.85349(16) 0.50013(3) 0.0303(2) Uani 1 1 d . . . . .
Cl1 Cl 0.16421(4) 0.64352(5) 0.49966(2) 0.04177(11) Uani 1 1 d . . . . .
H5A H 0.846(2) 0.850(3) 0.5207(5) 0.050(5) Uiso 1 1 d . . . . .
H5B H 0.830(2) 0.906(3) 0.4826(5) 0.051(5) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C6 1.3805(17) . ?
C1 C2 1.3831(16) . ?
C1 N1 1.4726(15) . ?
C2 C3 1.3824(16) . ?
C2 H2 0.95 . ?
C3 C4 1.3773(17) . ?
C3 N2 1.4711(15) . ?
C4 C5 1.3819(16) . ?
C4 H4 0.95 . ?
C5 C6 1.3825(16) . ?
C5 N3 1.4703(15) . ?
C6 H6 0.95 . ?
N1 O1 1.2130(16) . ?
N1 O2 1.2197(17) . ?
N2 O3 1.2205(17) . ?
N2 O4 1.2256(16) . ?
N3 O6 1.2229(16) . ?
N3 O5 1.2239(15) . ?
C7 O8 1.2131(14) . ?
C7 O7 1.2997(13) . ?
C7 C8 1.5064(14) . ?
C8 C9 1.4004(14) . ?
C8 C21 1.4014(14) . ?
C9 C10 1.4311(16) . ?
C9 C14 1.4370(15) . ?
C10 C11 1.3630(17) . ?
C10 H10 0.95 . ?
C11 C12 1.413(2) . ?
C11 H11 0.95 . ?
C12 C13 1.351(2) . ?
C12 H12 0.95 . ?
C13 C14 1.4328(17) . ?
C13 H13 0.95 . ?
C14 C15 1.3921(19) . ?
C15 C16 1.3935(18) . ?
C15 H15 0.95 . ?
C16 C17 1.4306(17) . ?
C16 C21 1.4391(15) . ?
C17 C18 1.354(2) . ?
C17 H17 0.95 . ?
C18 C19 1.420(2) . ?
C18 H18 0.95 . ?
C19 C20 1.3651(17) . ?
C19 H19 0.95 . ?
C20 C21 1.4298(15) . ?
C20 H20 0.95 . ?
O7 H7 0.84 . ?
C22 N4 1.3404(14) . ?
C22 N5 1.3518(16) . ?
C22 C23 1.4106(15) . ?
C23 C24 1.3677(18) . ?
C23 H23 0.95 . ?
C24 C25 1.3920(18) . ?
C24 H24 0.95 . ?
C25 C26 1.3710(16) . ?
C25 Cl1 1.7328(12) . ?
C26 N4 1.3457(15) . ?
C26 H26 0.95 . ?
N5 H5A 0.88(2) . ?
N5 H5B 0.85(2) . ?

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
C6 C1 C2 123.65(11) . . ?
C6 C1 N1 118.33(10) . . ?
C2 C1 N1 118.02(11) . . ?
C3 C2 C1 116.00(11) . . ?
C3 C2 H2 122 . . ?
C1 C2 H2 122 . . ?
C4 C3 C2 123.71(11) . . ?
C4 C3 N2 118.50(11) . . ?
C2 C3 N2 117.79(11) . . ?
C3 C4 C5 117.00(10) . . ?
C3 C4 H4 121.5 . . ?
C5 C4 H4 121.5 . . ?
C4 C5 C6 122.74(11) . . ?
C4 C5 N3 118.52(10) . . ?
C6 C5 N3 118.71(11) . . ?
C1 C6 C5 116.87(10) . . ?
C1 C6 H6 121.6 . . ?
C5 C6 H6 121.6 . . ?
O1 N1 O2 124.62(12) . . ?
O1 N1 C1 117.81(11) . . ?
O2 N1 C1 117.57(11) . . ?
O3 N2 O4 124.60(11) . . ?
O3 N2 C3 118.18(11) . . ?
O4 N2 C3 117.20(12) . . ?
O6 N3 O5 125.20(12) . . ?
O6 N3 C5 117.39(11) . . ?
O5 N3 C5 117.40(11) . . ?
O8 C7 O7 124.94(10) . . ?
O8 C7 C8 121.74(10) . . ?
O7 C7 C8 113.32(9) . . ?
C9 C8 C21 121.60(10) . . ?
C9 C8 C7 118.80(9) . . ?
C21 C8 C7 119.60(9) . . ?
C8 C9 C10 122.15(10) . . ?
C8 C9 C14 119.15(10) . . ?
C10 C9 C14 118.69(10) . . ?
C11 C10 C9 120.28(12) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 121.12(13) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C13 C12 C11 120.46(12) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 121.17(13) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
C15 C14 C13 122.45(12) . . ?
C15 C14 C9 119.28(10) . . ?
C13 C14 C9 118.28(12) . . ?
C14 C15 C16 121.66(10) . . ?
C14 C15 H15 119.2 . . ?
C16 C15 H15 119.2 . . ?
C15 C16 C17 121.88(11) . . ?
C15 C16 C21 119.58(11) . . ?
C17 C16 C21 118.48(11) . . ?
C18 C17 C16 120.79(12) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C17 C18 C19 120.99(12) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 H18 119.5 . . ?
C20 C19 C18 120.36(13) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C19 C20 C21 120.65(12) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
C8 C21 C20 122.61(10) . . ?
C8 C21 C16 118.70(10) . . ?
C20 C21 C16 118.65(10) . . ?
C7 O7 H7 109.5 . . ?
N4 C22 N5 117.64(10) . . ?
N4 C22 C23 120.20(10) . . ?
N5 C22 C23 122.16(11) . . ?
C24 C23 C22 119.08(11) . . ?
C24 C23 H23 120.5 . . ?
C22 C23 H23 120.5 . . ?
C23 C24 C25 119.62(11) . . ?
C23 C24 H24 120.2 . . ?
C25 C24 H24 120.2 . . ?
C26 C25 C24 119.12(11) . . ?
C26 C25 Cl1 120.44(10) . . ?
C24 C25 Cl1 120.44(9) . . ?
N4 C26 C25 121.39(11) . . ?
N4 C26 H26 119.3 . . ?
C25 C26 H26 119.3 . . ?
C22 N4 C26 120.58(10) . . ?
C22 N5 H5A 118.6(13) . . ?
C22 N5 H5B 119.9(13) . . ?
H5A N5 H5B 120.3(18) . . ?

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
C6 C1 C2 C3 0.29(18) . . . . ?
N1 C1 C2 C3 179.89(11) . . . . ?
C1 C2 C3 C4 -1.32(17) . . . . ?
C1 C2 C3 N2 177.85(10) . . . . ?
C2 C3 C4 C5 0.89(17) . . . . ?
N2 C3 C4 C5 -178.28(10) . . . . ?
C3 C4 C5 C6 0.63(17) . . . . ?
C3 C4 C5 N3 -177.76(10) . . . . ?
C2 C1 C6 C5 1.09(18) . . . . ?
N1 C1 C6 C5 -178.51(11) . . . . ?
C4 C5 C6 C1 -1.56(17) . . . . ?
N3 C5 C6 C1 176.82(10) . . . . ?
C6 C1 N1 O1 -4.35(19) . . . . ?
C2 C1 N1 O1 176.02(14) . . . . ?
C6 C1 N1 O2 175.60(14) . . . . ?
C2 C1 N1 O2 -4.0(2) . . . . ?
C4 C3 N2 O3 -169.63(12) . . . . ?
C2 C3 N2 O3 11.15(17) . . . . ?
C4 C3 N2 O4 12.16(16) . . . . ?
C2 C3 N2 O4 -167.06(11) . . . . ?
C4 C5 N3 O6 -163.59(11) . . . . ?
C6 C5 N3 O6 17.96(16) . . . . ?
C4 C5 N3 O5 17.40(16) . . . . ?
C6 C5 N3 O5 -161.05(11) . . . . ?
O8 C7 C8 C9 101.98(13) . . . . ?
O7 C7 C8 C9 -77.33(13) . . . . ?
O8 C7 C8 C21 -78.73(14) . . . . ?
O7 C7 C8 C21 101.96(12) . . . . ?
C21 C8 C9 C10 -179.32(10) . . . . ?
C7 C8 C9 C10 -0.04(15) . . . . ?
C21 C8 C9 C14 1.16(16) . . . . ?
C7 C8 C9 C14 -179.56(10) . . . . ?
C8 C9 C10 C11 -179.35(11) . . . . ?
C14 C9 C10 C11 0.18(17) . . . . ?
C9 C10 C11 C12 0.23(19) . . . . ?
C10 C11 C12 C13 -0.2(2) . . . . ?
C11 C12 C13 C14 -0.2(2) . . . . ?
C12 C13 C14 C15 -179.21(13) . . . . ?
C12 C13 C14 C9 0.59(19) . . . . ?
C8 C9 C14 C15 -1.22(16) . . . . ?
C10 C9 C14 C15 179.24(11) . . . . ?
C8 C9 C14 C13 178.96(11) . . . . ?
C10 C9 C14 C13 -0.57(16) . . . . ?
C13 C14 C15 C16 179.60(12) . . . . ?
C9 C14 C15 C16 -0.21(18) . . . . ?
C14 C15 C16 C17 -175.41(12) . . . . ?
C14 C15 C16 C21 1.69(18) . . . . ?
C15 C16 C17 C18 176.54(12) . . . . ?
C21 C16 C17 C18 -0.60(18) . . . . ?
C16 C17 C18 C19 2.6(2) . . . . ?
C17 C18 C19 C20 -1.7(2) . . . . ?
C18 C19 C20 C21 -1.10(19) . . . . ?
C9 C8 C21 C20 177.82(10) . . . . ?
C7 C8 C21 C20 -1.46(16) . . . . ?
C9 C8 C21 C16 0.30(16) . . . . ?
C7 C8 C21 C16 -178.97(9) . . . . ?
C19 C20 C21 C8 -174.53(11) . . . . ?
C19 C20 C21 C16 2.99(17) . . . . ?
C15 C16 C21 C8 -1.73(16) . . . . ?
C17 C16 C21 C8 175.47(10) . . . . ?
C15 C16 C21 C20 -179.34(11) . . . . ?
C17 C16 C21 C20 -2.14(16) . . . . ?
N4 C22 C23 C24 0.25(17) . . . . ?
N5 C22 C23 C24 179.71(11) . . . . ?
C22 C23 C24 C25 0.64(17) . . . . ?
C23 C24 C25 C26 -0.79(18) . . . . ?
C23 C24 C25 Cl1 178.80(9) . . . . ?
C24 C25 C26 N4 0.04(18) . . . . ?
Cl1 C25 C26 N4 -179.54(9) . . . . ?
N5 C22 N4 C26 179.51(10) . . . . ?
C23 C22 N4 C26 -1.01(16) . . . . ?
C25 C26 N4 C22 0.87(17) . . . . ?

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
O7 H7 N4 0.84 1.71 2.5392(12) 167 . yes
N5 H5A O4 0.88(2) 2.42(2) 3.1834(16) 145(2) 1_565 yes
N5 H5B O4 0.85(2) 2.29(2) 3.1065(15) 162(2) 3_766 yes



# END of CIF
