# 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_sh434
_database_code_depnum_ccdc_archive 'CCDC 2125221'
loop_
_audit_author_name
_audit_author_address
'Kyrill Yu.  Suponitsky'
;A N Nesmeyanov Institute of Organoelement Compounds, Moscow, Russia
Russia
;
_audit_update_record             
;
2021-11-30 deposited with the CCDC.	2022-08-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H8 Cl2 N4 O4'
_chemical_formula_sum            'C4 H8 Cl2 N4 O4'
_chemical_formula_weight         247.04

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                   5.8212(4)
_cell_length_b                   11.9073(9)
_cell_length_c                   7.3664(5)
_cell_angle_alpha                90
_cell_angle_beta                 112.7940(10)
_cell_angle_gamma                90
_cell_volume                     470.72(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3229
_cell_measurement_theta_min      3.42
_cell_measurement_theta_max      28.79

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.743
_exptl_crystal_F_000             252
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.686
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.843
_exptl_absorpt_correction_T_max  0.947
_exptl_absorpt_process_details   'SADABS-2014/5 (Bruker,2014/5)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5559
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.422
_diffrn_reflns_theta_max         28.844
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1209
_reflns_number_gt                1115
_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       'APEX (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_publication_material  
'SHELXL-2014/6 (Sheldrick, 2014) and PLATON (Spek, 2015)'
_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)+(0.0247P)²+0.2392P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1209
_refine_ls_number_parameters     64
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0272
_refine_ls_R_factor_gt           0.0248
_refine_ls_wR_factor_ref         0.0615
_refine_ls_wR_factor_gt          0.0599
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.80216(5) 0.41020(3) 0.58302(4) 0.02243(10) Uani 1 1 d . . . . .
O1 O 0.32876(19) 0.26164(8) 0.29010(15) 0.0286(2) Uani 1 1 d . . . . .
O2 O 0.12010(16) 0.38589(8) 0.06970(13) 0.0230(2) Uani 1 1 d . . . . .
N1 N 0.53482(18) 0.39061(8) 0.19253(14) 0.0161(2) Uani 1 1 d . . . . .
N2 N 0.31467(19) 0.34313(8) 0.18447(15) 0.0181(2) Uani 1 1 d . . . . .
C1 C 0.7577(2) 0.35140(10) 0.34403(17) 0.0187(2) Uani 1 1 d . . . . .
H1A H 0.9018 0.3717 0.3109 0.022 Uiso 1 1 calc R U . . .
H1B H 0.7518 0.2685 0.3510 0.022 Uiso 1 1 calc R U . . .
C2 C 0.5194(2) 0.50352(9) 0.10852(16) 0.0160(2) Uani 1 1 d . . . . .
H2A H 0.6749 0.5452 0.1823 0.019 Uiso 1 1 calc R U . . .
H2B H 0.3790 0.5450 0.1213 0.019 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C1 1.8176(12) . ?
O1 N2 1.2265(14) . ?
O2 N2 1.2308(14) . ?
N1 N2 1.3808(14) . ?
N1 C1 1.4230(15) . ?
N1 C2 1.4682(14) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C2 1.528(2) 3_665 ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?

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
N2 N1 C1 116.65(9) . . ?
N2 N1 C2 116.91(9) . . ?
C1 N1 C2 121.29(10) . . ?
O1 N2 O2 125.50(10) . . ?
O1 N2 N1 117.63(10) . . ?
O2 N2 N1 116.87(10) . . ?
N1 C1 Cl1 112.19(8) . . ?
N1 C1 H1A 109.2 . . ?
Cl1 C1 H1A 109.2 . . ?
N1 C1 H1B 109.2 . . ?
Cl1 C1 H1B 109.2 . . ?
H1A C1 H1B 107.9 . . ?
N1 C2 C2 110.54(11) . 3_665 ?
N1 C2 H2A 109.5 . . ?
C2 C2 H2A 109.5 3_665 . ?
N1 C2 H2B 109.5 . . ?
C2 C2 H2B 109.5 3_665 . ?
H2A C2 H2B 108.1 . . ?

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
C1 N1 N2 O1 -9.20(15) . . . . ?
C2 N1 N2 O1 -164.18(10) . . . . ?
C1 N1 N2 O2 171.51(10) . . . . ?
C2 N1 N2 O2 16.52(14) . . . . ?
N2 N1 C1 Cl1 -76.83(12) . . . . ?
C2 N1 C1 Cl1 76.99(12) . . . . ?
N2 N1 C2 C2 -91.07(14) . . . 3_665 ?
C1 N1 C2 C2 115.18(14) . . . 3_665 ?

_refine_diff_density_max         0.415
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.052

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_sh449
_database_code_depnum_ccdc_archive 'CCDC 2125222'
loop_
_audit_author_name
_audit_author_address
'Kyrill Yu.  Suponitsky'
;A N Nesmeyanov Institute of Organoelement Compounds, Moscow, Russia
Russia
;
_audit_update_record             
;
2021-11-30 deposited with the CCDC.	2022-08-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H10 Cl2 N8 O8'
_chemical_formula_sum            'C5 H10 Cl2 N8 O8'
_chemical_formula_weight         381.11

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           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 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+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   28.4221(9)
_cell_length_b                   5.9548(2)
_cell_length_c                   25.7279(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4354.4(3)
_cell_formula_units_Z            12
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7655
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      25.99

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.744
_exptl_crystal_F_000             2328
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.506
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.941
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_process_details   'SADABS-2014/5 (Bruker,2014/5)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32765
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_av_R_equivalents  0.0610
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.135
_diffrn_reflns_theta_max         26.072
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4304
_reflns_number_gt                3615
_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       'APEX (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_publication_material  
'SHELXL-2014/6 (Sheldrick, 2014) and PLATON (Spek, 2015)'
_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)+(0.0197P)²+9.9164P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4304
_refine_ls_number_parameters     312
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0721
_refine_ls_R_factor_gt           0.0569
_refine_ls_wR_factor_ref         0.1029
_refine_ls_wR_factor_gt          0.0973
_refine_ls_goodness_of_fit_ref   1.192
_refine_ls_restrained_S_all      1.192
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.21725(3) 0.75045(16) 0.49228(3) 0.0251(2) Uani 1 1 d . . . . .
Cl2 Cl 0.13160(3) 0.5796(2) 0.91918(3) 0.0373(3) Uani 1 1 d . . . . .
O1 O 0.16628(9) 1.2303(4) 0.53895(9) 0.0257(6) Uani 1 1 d . . . . .
O2 O 0.18340(9) 1.1640(4) 0.62011(9) 0.0223(5) Uani 1 1 d . . . . .
O3 O 0.09748(8) 0.5362(4) 0.60655(9) 0.0218(5) Uani 1 1 d . . . . .
O4 O 0.08467(7) 0.5816(4) 0.68965(9) 0.0201(5) Uani 1 1 d . . . . .
O5 O 0.23785(7) 0.5610(4) 0.69720(8) 0.0155(5) Uani 1 1 d . . . . .
O6 O 0.23093(8) 0.4167(4) 0.77487(8) 0.0183(5) Uani 1 1 d . . . . .
O7 O 0.15374(9) 1.0522(4) 0.80412(9) 0.0241(6) Uani 1 1 d . . . . .
O8 O 0.19010(11) 1.0424(4) 0.87877(10) 0.0401(7) Uani 1 1 d . . . . .
N1 N 0.16063(9) 0.8804(4) 0.56986(10) 0.0133(6) Uani 1 1 d . . . . .
N2 N 0.17113(9) 1.1070(4) 0.57649(10) 0.0169(6) Uani 1 1 d . . . . .
N3 N 0.15033(8) 0.7113(4) 0.65485(9) 0.0116(5) Uani 1 1 d . . . . .
N4 N 0.10842(9) 0.6035(4) 0.65004(10) 0.0150(6) Uani 1 1 d . . . . .
N5 N 0.17446(8) 0.6375(4) 0.74370(10) 0.0117(5) Uani 1 1 d . . . . .
N6 N 0.21724(9) 0.5328(4) 0.73847(10) 0.0134(6) Uani 1 1 d . . . . .
N7 N 0.17777(9) 0.7236(4) 0.83542(10) 0.0150(6) Uani 1 1 d . . . . .
N8 N 0.17331(10) 0.9552(5) 0.84012(11) 0.0213(6) Uani 1 1 d . . . . .
C1 C 0.15896(11) 0.8017(5) 0.51723(12) 0.0160(7) Uani 1 1 d . . . . .
H1A H 0.1430 0.9149 0.4952 0.019 Uiso 1 1 calc R U . . .
H1B H 0.1404 0.6611 0.5157 0.019 Uiso 1 1 calc R U . . .
C2 C 0.17977(10) 0.7287(5) 0.60928(11) 0.0126(6) Uani 1 1 d . . . . .
H2A H 0.1837 0.5776 0.5939 0.015 Uiso 1 1 calc R U . . .
H2B H 0.2113 0.7830 0.6198 0.015 Uiso 1 1 calc R U . . .
C3 C 0.16238(10) 0.8067(5) 0.70506(11) 0.0106(6) Uani 1 1 d . . . . .
H3A H 0.1354 0.8958 0.7179 0.013 Uiso 1 1 calc R U . . .
H3B H 0.1894 0.9101 0.7007 0.013 Uiso 1 1 calc R U . . .
C4 C 0.15141(11) 0.6191(5) 0.79337(11) 0.0143(6) Uani 1 1 d . . . . .
H4A H 0.1467 0.4582 0.8016 0.017 Uiso 1 1 calc R U . . .
H4B H 0.1200 0.6904 0.7911 0.017 Uiso 1 1 calc R U . . .
C5 C 0.18550(11) 0.6035(6) 0.88277(12) 0.0206(7) Uani 1 1 d . . . . .
H5A H 0.2093 0.6831 0.9039 0.025 Uiso 1 1 calc R U . . .
H5B H 0.1977 0.4518 0.8748 0.025 Uiso 1 1 calc R U . . .
Cl1' Cl 0.04499(3) 0.76956(15) 0.47470(3) 0.02278(19) Uani 1 1 d . . . . .
O1' O 0.01324(8) 0.2916(4) 0.41549(9) 0.0232(5) Uani 1 1 d . . . . .
O2' O 0.03388(8) 0.3494(4) 0.33482(8) 0.0171(5) Uani 1 1 d . . . . .
O3' O -0.05928(8) 0.9617(4) 0.34523(8) 0.0209(5) Uani 1 1 d . . . . .
O4' O -0.07604(8) 0.8770(4) 0.26487(9) 0.0222(5) Uani 1 1 d . . . . .
N1' N 0.00937(9) 0.6362(4) 0.38274(10) 0.0129(5) Uani 1 1 d . . . . .
N2' N 0.01952(9) 0.4112(4) 0.37776(10) 0.0150(6) Uani 1 1 d . . . . .
N3' N -0.00664(9) 0.7856(4) 0.29656(9) 0.0125(5) Uani 1 1 d . . . . .
N4' N -0.04984(9) 0.8803(4) 0.30298(10) 0.0161(6) Uani 1 1 d . . . . .
C1' C -0.00468(11) 0.7174(6) 0.43268(12) 0.0151(7) Uani 1 1 d . . . . .
H1'A H -0.0256 0.6057 0.4493 0.018 Uiso 1 1 calc R U . . .
H1'B H -0.0227 0.8583 0.4283 0.018 Uiso 1 1 calc R U . . .
C2' C 0.02455(10) 0.7849(5) 0.34090(11) 0.0131(6) Uani 1 1 d . . . . .
H2'A H 0.0270 0.9398 0.3546 0.016 Uiso 1 1 calc R U . . .
H2'B H 0.0563 0.7385 0.3293 0.016 Uiso 1 1 calc R U . . .
C3' C 0.0000 0.6517(7) 0.2500 0.0111(9) Uani 1 2 d S T P . .
H3'A H -0.0270 0.5570 0.2454 0.013 Uiso 1 1 d R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C1 1.803(3) . ?
Cl2 C5 1.802(3) . ?
O1 N2 1.221(3) . ?
O2 N2 1.223(3) . ?
O3 N4 1.228(3) . ?
O4 N4 1.229(3) . ?
O5 N6 1.224(3) . ?
O6 N6 1.227(3) . ?
O7 N8 1.225(3) . ?
O8 N8 1.219(3) . ?
N1 N2 1.393(3) . ?
N1 C1 1.434(4) . ?
N1 C2 1.463(4) . ?
N3 N4 1.359(3) . ?
N3 C2 1.444(4) . ?
N3 C3 1.452(4) . ?
N5 N6 1.373(3) . ?
N5 C4 1.440(4) . ?
N5 C3 1.457(4) . ?
N7 N8 1.390(4) . ?
N7 C5 1.429(4) . ?
N7 C4 1.456(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
Cl1' C1' 1.805(3) . ?
O1' N2' 1.217(3) . ?
O2' N2' 1.234(3) . ?
O3' N4' 1.220(3) . ?
O4' N4' 1.231(3) . ?
N1' N2' 1.376(3) . ?
N1' C1' 1.430(4) . ?
N1' C2' 1.459(4) . ?
N3' N4' 1.361(3) . ?
N3' C2' 1.445(4) . ?
N3' C3' 1.451(3) . ?
C1' H1'A 0.9900 . ?
C1' H1'B 0.9900 . ?
C2' H2'A 0.9900 . ?
C2' H2'B 0.9900 . ?
C3' N3' 1.451(3) 3 ?
C3' H3'A 0.9600 . ?

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
N2 N1 C1 116.1(2) . . ?
N2 N1 C2 115.7(2) . . ?
C1 N1 C2 117.7(2) . . ?
O1 N2 O2 126.2(3) . . ?
O1 N2 N1 117.5(3) . . ?
O2 N2 N1 116.3(3) . . ?
N4 N3 C2 117.9(2) . . ?
N4 N3 C3 118.2(2) . . ?
C2 N3 C3 123.9(2) . . ?
O3 N4 O4 125.5(3) . . ?
O3 N4 N3 117.3(2) . . ?
O4 N4 N3 117.1(2) . . ?
N6 N5 C4 117.1(2) . . ?
N6 N5 C3 117.1(2) . . ?
C4 N5 C3 123.4(2) . . ?
O5 N6 O6 126.0(2) . . ?
O5 N6 N5 116.5(2) . . ?
O6 N6 N5 117.5(2) . . ?
N8 N7 C5 115.9(3) . . ?
N8 N7 C4 116.2(2) . . ?
C5 N7 C4 119.9(3) . . ?
O8 N8 O7 126.4(3) . . ?
O8 N8 N7 117.2(3) . . ?
O7 N8 N7 116.3(3) . . ?
N1 C1 Cl1 111.2(2) . . ?
N1 C1 H1A 109.4 . . ?
Cl1 C1 H1A 109.4 . . ?
N1 C1 H1B 109.4 . . ?
Cl1 C1 H1B 109.4 . . ?
H1A C1 H1B 108.0 . . ?
N3 C2 N1 113.1(2) . . ?
N3 C2 H2A 109.0 . . ?
N1 C2 H2A 109.0 . . ?
N3 C2 H2B 109.0 . . ?
N1 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
N3 C3 N5 113.1(2) . . ?
N3 C3 H3A 109.0 . . ?
N5 C3 H3A 109.0 . . ?
N3 C3 H3B 109.0 . . ?
N5 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
N5 C4 N7 113.1(2) . . ?
N5 C4 H4A 109.0 . . ?
N7 C4 H4A 109.0 . . ?
N5 C4 H4B 109.0 . . ?
N7 C4 H4B 109.0 . . ?
H4A C4 H4B 107.8 . . ?
N7 C5 Cl2 110.6(2) . . ?
N7 C5 H5A 109.5 . . ?
Cl2 C5 H5A 109.5 . . ?
N7 C5 H5B 109.5 . . ?
Cl2 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
N2' N1' C1' 118.1(2) . . ?
N2' N1' C2' 117.4(2) . . ?
C1' N1' C2' 122.7(3) . . ?
O1' N2' O2' 126.0(3) . . ?
O1' N2' N1' 117.7(3) . . ?
O2' N2' N1' 116.3(2) . . ?
N4' N3' C2' 117.3(2) . . ?
N4' N3' C3' 116.4(2) . . ?
C2' N3' C3' 124.8(2) . . ?
O3' N4' O4' 125.6(3) . . ?
O3' N4' N3' 118.1(3) . . ?
O4' N4' N3' 116.3(2) . . ?
N1' C1' Cl1' 112.2(2) . . ?
N1' C1' H1'A 109.2 . . ?
Cl1' C1' H1'A 109.2 . . ?
N1' C1' H1'B 109.2 . . ?
Cl1' C1' H1'B 109.2 . . ?
H1'A C1' H1'B 107.9 . . ?
N3' C2' N1' 113.7(2) . . ?
N3' C2' H2'A 108.8 . . ?
N1' C2' H2'A 108.8 . . ?
N3' C2' H2'B 108.8 . . ?
N1' C2' H2'B 108.8 . . ?
H2'A C2' H2'B 107.7 . . ?
N3' C3' N3' 113.4(3) . 3 ?
N3' C3' H3'A 108.7 . . ?
N3' C3' H3'A 109.0 3 . ?

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
C1 N1 N2 O1 18.2(4) . . . . ?
C2 N1 N2 O1 162.3(3) . . . . ?
C1 N1 N2 O2 -163.5(3) . . . . ?
C2 N1 N2 O2 -19.3(4) . . . . ?
C2 N3 N4 O3 -3.0(4) . . . . ?
C3 N3 N4 O3 175.5(3) . . . . ?
C2 N3 N4 O4 177.0(3) . . . . ?
C3 N3 N4 O4 -4.5(4) . . . . ?
C4 N5 N6 O5 -175.7(3) . . . . ?
C3 N5 N6 O5 -12.5(4) . . . . ?
C4 N5 N6 O6 5.7(4) . . . . ?
C3 N5 N6 O6 168.9(3) . . . . ?
C5 N7 N8 O8 22.0(4) . . . . ?
C4 N7 N8 O8 170.9(3) . . . . ?
C5 N7 N8 O7 -159.7(3) . . . . ?
C4 N7 N8 O7 -10.8(4) . . . . ?
N2 N1 C1 Cl1 79.8(3) . . . . ?
C2 N1 C1 Cl1 -63.6(3) . . . . ?
N4 N3 C2 N1 69.8(3) . . . . ?
C3 N3 C2 N1 -108.7(3) . . . . ?
N2 N1 C2 N3 84.8(3) . . . . ?
C1 N1 C2 N3 -131.7(3) . . . . ?
N4 N3 C3 N5 72.5(3) . . . . ?
C2 N3 C3 N5 -109.0(3) . . . . ?
N6 N5 C3 N3 73.3(3) . . . . ?
C4 N5 C3 N3 -124.6(3) . . . . ?
N6 N5 C4 N7 63.3(3) . . . . ?
C3 N5 C4 N7 -98.7(3) . . . . ?
N8 N7 C4 N5 80.9(3) . . . . ?
C5 N7 C4 N5 -131.5(3) . . . . ?
N8 N7 C5 Cl2 76.4(3) . . . . ?
C4 N7 C5 Cl2 -71.3(3) . . . . ?
C1' N1' N2' O1' 4.3(4) . . . . ?
C2' N1' N2' O1' 169.5(3) . . . . ?
C1' N1' N2' O2' -176.3(2) . . . . ?
C2' N1' N2' O2' -11.1(4) . . . . ?
C2' N3' N4' O3' 1.2(4) . . . . ?
C3' N3' N4' O3' 168.0(3) . . . . ?
C2' N3' N4' O4' -179.3(3) . . . . ?
C3' N3' N4' O4' -12.5(4) . . . . ?
N2' N1' C1' Cl1' 81.6(3) . . . . ?
C2' N1' C1' Cl1' -82.8(3) . . . . ?
N4' N3' C2' N1' 69.1(3) . . . . ?
C3' N3' C2' N1' -96.4(3) . . . . ?
N2' N1' C2' N3' 81.0(3) . . . . ?
C1' N1' C2' N3' -114.5(3) . . . . ?
N4' N3' C3' N3' 76.9(2) . . . 3 ?
C2' N3' C3' N3' -117.4(3) . . . 3 ?

_refine_diff_density_max         0.353
_refine_diff_density_min         -0.521
_refine_diff_density_rms         0.076

_shelxl_version_number           2014/6

