# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_shrv343
_database_code_depnum_ccdc_archive 'CCDC 1435626'
_audit_update_record             
;
2015-11-09 deposited with the CCDC.
2016-05-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 Cl8 N10 O8'
_chemical_formula_sum            'C6 Cl8 N10 O8'
_chemical_formula_weight         623.76

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'
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                   6.1067(2)
_cell_length_b                   13.7465(4)
_cell_length_c                   12.4167(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.0240(10)
_cell_angle_gamma                90
_cell_volume                     1036.57(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5015
_cell_measurement_theta_min      2.96
_cell_measurement_theta_max      27.52

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.998
_exptl_crystal_F_000             612
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.269
_exptl_crystal_size_mid          0.237
_exptl_crystal_size_min          0.046
_exptl_absorpt_coefficient_mu    1.148
_shelx_estimated_absorpt_T_min   0.748
_shelx_estimated_absorpt_T_max   0.949
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2008/1 (Bruker, 2008)'
_exptl_absorpt_correction_T_min  0.6810
_exptl_absorpt_correction_T_max  0.7456

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10729
_diffrn_reflns_av_unetI/netI     0.0144
_diffrn_reflns_av_R_equivalents  0.0184
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.300
_diffrn_reflns_theta_max         27.621
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2376
_reflns_number_gt                2073
_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       'Bruker APEX2 v2014.11-0 (Bruker, 2009)'
_computing_cell_refinement       'Bruker APEX2 v2014.11-0 (Bruker, 2009)'
_computing_data_reduction        
;
Bruker SAINT v7.68A (Bruker, 2009), Bruker XPREP v2014/2 (Bruker, 2008)
;
_computing_structure_solution    'Bruker SHELXTL v2014/7 (Bruker, 2008)'
_computing_structure_refinement  
'SHELXL-2014/7 (Sheldrick, 2014) within WINGX (Farrugia, 2012)'
_computing_molecular_graphics    'Bruker SHELXTL v2014/7 (Bruker, 2008)'
_computing_publication_material  'Bruker SHELXTL v2014/7 (Bruker, 2008)'
_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)+(0.0463P)²+0.3395P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   .
_refine_ls_hydrogen_treatment    undef
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2376
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0274
_refine_ls_wR_factor_ref         0.0804
_refine_ls_wR_factor_gt          0.0757
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_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
O1 O 0.8600(3) 0.30952(11) 0.07985(12) 0.0568(4) Uani 1 1 d . . . . .
O2 O 0.5864(3) 0.37655(13) -0.01681(11) 0.0646(4) Uani 1 1 d . . . . .
N3 N 0.6907(3) 0.35548(11) 0.06690(12) 0.0392(3) Uani 1 1 d . . . . .
C4 C 0.6001(3) 0.39293(11) 0.17285(12) 0.0303(3) Uani 1 1 d . . . . .
N5 N 0.6847(3) 0.31669(10) 0.25860(12) 0.0421(3) Uani 1 1 d . . . . .
O6 O 0.8585(3) 0.33619(11) 0.30948(12) 0.0597(4) Uani 1 1 d . . . . .
O7 O 0.5759(3) 0.24421(12) 0.26374(14) 0.0713(5) Uani 1 1 d . . . . .
Cl8 Cl 0.31813(7) 0.39486(4) 0.15316(4) 0.05255(15) Uani 1 1 d . . . . .
C9 C 0.7031(3) 0.49142(11) 0.20182(12) 0.0295(3) Uani 1 1 d . . . . .
N10 N 0.8218(2) 0.52651(11) 0.13380(11) 0.0367(3) Uani 1 1 d . . . . .
Cl11 Cl 0.93104(9) 0.63851(4) 0.15955(4) 0.05306(15) Uani 1 1 d . . . . .
N12 N 0.6595(2) 0.54059(10) 0.29903(11) 0.0357(3) Uani 1 1 d . . . . .
N13 N 0.5477(3) 0.49101(10) 0.35491(11) 0.0367(3) Uani 1 1 d . . . . .
C14 C 0.4900(3) 0.53941(12) 0.45473(13) 0.0349(3) Uani 1 1 d . . . . .
Cl15 Cl 0.20973(8) 0.57297(4) 0.42839(4) 0.04981(14) Uani 1 1 d . . . . .
Cl16 Cl 0.65420(9) 0.64134(3) 0.49457(4) 0.04564(14) Uani 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0520(8) 0.0600(9) 0.0618(9) -0.0102(7) 0.0215(7) 0.0083(7)
O2 0.0722(11) 0.0908(12) 0.0292(7) -0.0091(7) -0.0013(7) 0.0005(9)
N3 0.0421(8) 0.0412(8) 0.0354(7) -0.0089(6) 0.0097(6) -0.0077(6)
C4 0.0294(8) 0.0332(7) 0.0288(7) -0.0008(6) 0.0050(6) -0.0014(6)
N5 0.0586(10) 0.0328(7) 0.0356(7) 0.0020(6) 0.0078(7) 0.0028(7)
O6 0.0676(10) 0.0517(8) 0.0546(8) 0.0008(6) -0.0176(7) 0.0150(7)
O7 0.1024(13) 0.0430(8) 0.0695(10) 0.0141(7) 0.0144(9) -0.0177(8)
Cl8 0.0282(2) 0.0691(3) 0.0602(3) -0.0121(2) 0.00445(19) -0.0063(2)
C9 0.0314(8) 0.0315(7) 0.0257(7) 0.0009(5) 0.0035(6) -0.0012(6)
N10 0.0378(8) 0.0424(8) 0.0305(7) 0.0001(6) 0.0055(5) -0.0099(6)
Cl11 0.0644(3) 0.0505(3) 0.0454(3) 0.00287(19) 0.0109(2) -0.0269(2)
N12 0.0447(8) 0.0320(7) 0.0320(7) -0.0007(5) 0.0117(6) -0.0031(6)
N13 0.0485(8) 0.0339(7) 0.0294(7) -0.0016(5) 0.0114(6) -0.0036(6)
C14 0.0420(9) 0.0321(8) 0.0316(8) -0.0002(6) 0.0082(7) 0.0021(7)
Cl15 0.0425(3) 0.0584(3) 0.0485(3) 0.0079(2) 0.00492(19) 0.0184(2)
Cl16 0.0660(3) 0.0317(2) 0.0410(2) -0.00582(15) 0.0144(2) -0.01128(19)

_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
O1 N3 1.208(2) . ?
O2 N3 1.196(2) . ?
N3 C4 1.567(2) . ?
C4 C9 1.520(2) . ?
C4 N5 1.544(2) . ?
C4 Cl8 1.7135(17) . ?
N5 O7 1.203(2) . ?
N5 O6 1.207(2) . ?
C9 N10 1.265(2) . ?
C9 N12 1.4326(19) . ?
N10 Cl11 1.6948(15) . ?
N12 N13 1.2293(19) . ?
N13 C14 1.482(2) . ?
C14 C14 1.557(3) 3_666 ?
C14 Cl16 1.7632(17) . ?
C14 Cl15 1.7698(18) . ?

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
O2 N3 O1 127.77(16) . . ?
O2 N3 C4 116.57(15) . . ?
O1 N3 C4 115.65(14) . . ?
C9 C4 N5 109.94(12) . . ?
C9 C4 N3 108.50(12) . . ?
N5 C4 N3 103.53(12) . . ?
C9 C4 Cl8 113.88(11) . . ?
N5 C4 Cl8 111.57(11) . . ?
N3 C4 Cl8 108.86(11) . . ?
O7 N5 O6 128.06(17) . . ?
O7 N5 C4 116.86(16) . . ?
O6 N5 C4 115.00(14) . . ?
N10 C9 N12 123.57(14) . . ?
N10 C9 C4 115.71(14) . . ?
N12 C9 C4 120.70(13) . . ?
C9 N10 Cl11 117.53(12) . . ?
N13 N12 C9 112.17(13) . . ?
N12 N13 C14 114.72(13) . . ?
N13 C14 C14 106.50(16) . 3_666 ?
N13 C14 Cl16 114.41(11) . . ?
C14 C14 Cl16 110.57(15) 3_666 . ?
N13 C14 Cl15 105.83(11) . . ?
C14 C14 Cl15 108.41(15) 3_666 . ?
Cl16 C14 Cl15 110.80(9) . . ?

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
O2 N3 C4 C9 -91.18(18) . . . . ?
O1 N3 C4 C9 87.96(17) . . . . ?
O2 N3 C4 N5 152.05(16) . . . . ?
O1 N3 C4 N5 -28.80(18) . . . . ?
O2 N3 C4 Cl8 33.26(19) . . . . ?
O1 N3 C4 Cl8 -147.60(13) . . . . ?
C9 C4 N5 O7 160.04(15) . . . . ?
N3 C4 N5 O7 -84.21(18) . . . . ?
Cl8 C4 N5 O7 32.71(19) . . . . ?
C9 C4 N5 O6 -22.82(19) . . . . ?
N3 C4 N5 O6 92.93(16) . . . . ?
Cl8 C4 N5 O6 -150.15(13) . . . . ?
N5 C4 C9 N10 117.99(15) . . . . ?
N3 C4 C9 N10 5.43(19) . . . . ?
Cl8 C4 C9 N10 -115.98(15) . . . . ?
N5 C4 C9 N12 -63.83(18) . . . . ?
N3 C4 C9 N12 -176.40(13) . . . . ?
Cl8 C4 C9 N12 62.20(17) . . . . ?
N12 C9 N10 Cl11 -0.9(2) . . . . ?
C4 C9 N10 Cl11 177.27(11) . . . . ?
N10 C9 N12 N13 -177.18(16) . . . . ?
C4 C9 N12 N13 4.8(2) . . . . ?
C9 N12 N13 C14 -177.83(13) . . . . ?
N12 N13 C14 C14 -140.14(18) . . . 3_666 ?
N12 N13 C14 Cl16 -17.66(19) . . . . ?
N12 N13 C14 Cl15 104.62(15) . . . . ?

_refine_diff_density_max         0.533
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.047


# start Validation Reply Form
_vrf_PLAT015_shrv343             
;
PROBLEM: No _shelx_hkl_file record in SHELXL20xy CIF ....     Please Do ! 
RESPONSE: It is our policy to routinely not supply the HKL file unless 
specifically required.

;
_vrf_PLAT230_shrv343             
;
PROBLEM: Hirshfeld Test Diff for    Cl15   --  C14     ..        7.3 su    
RESPONSE: ...
;
# end Validation Reply Form
####################################################################### 
# 
# 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_shrv333
_database_code_depnum_ccdc_archive 'CCDC 1435627'
_audit_update_record             
;
2015-11-09 deposited with the CCDC.
2016-05-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H2 Cl2 N10 O8'
_chemical_formula_sum            'C4 H2 Cl2 N10 O8'
_chemical_formula_weight         389.06

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                   10.3037(3)
_cell_length_b                   9.6323(3)
_cell_length_c                   14.3934(4)
_cell_angle_alpha                90
_cell_angle_beta                 107.9270(10)
_cell_angle_gamma                90
_cell_volume                     1359.17(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4109
_cell_measurement_theta_min      2.96
_cell_measurement_theta_max      26.01

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.901
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.221
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.085
_exptl_absorpt_coefficient_mu    0.547
_shelx_estimated_absorpt_T_min   0.889
_shelx_estimated_absorpt_T_max   0.955
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2008/1 (Bruker, 2008)'
_exptl_absorpt_correction_T_min  0.6859
_exptl_absorpt_correction_T_max  0.7454

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12853
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.077
_diffrn_reflns_theta_max         26.486
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2796
_reflns_number_gt                2257
_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       'Bruker APEX2 v2014.11-0 (Bruker, 2009)'
_computing_cell_refinement       'Bruker APEX2 v2014.11-0 (Bruker, 2009)'
_computing_data_reduction        
;
Bruker SAINT v7.68A (Bruker, 2009), Bruker XPREP v2014/2 (Bruker, 2008)
;
_computing_structure_solution    'Bruker SHELXTL v2014/7 (Bruker, 2008)'
_computing_structure_refinement  
'SHELXL-2014/7 (Sheldrick, 2014) within WINGX (Farrugia, 2012)'
_computing_molecular_graphics    'Bruker SHELXTL v2014/7 (Bruker, 2008)'
_computing_publication_material  'Bruker SHELXTL v2014/7 (Bruker, 2008)'
_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)+(0.0648P)²+0.3266P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2796
_refine_ls_number_parameters     223
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0329
_refine_ls_wR_factor_ref         0.1058
_refine_ls_wR_factor_gt          0.0966
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_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
O1 O 0.42929(17) 0.3362(2) 0.88744(13) 0.0587(5) Uani 1 1 d . . . . .
O2 O 0.37641(19) 0.4006(2) 1.01408(13) 0.0670(6) Uani 1 1 d . . . . .
N3 N 0.35210(17) 0.36156(18) 0.93206(12) 0.0333(4) Uani 1 1 d . . . . .
O4 O 0.2644(2) 0.11208(18) 0.94060(14) 0.0596(5) Uani 1 1 d . . . . .
O5 O 0.04958(19) 0.1617(2) 0.89862(13) 0.0613(5) Uani 1 1 d . . . . .
N6 N 0.1674(2) 0.18716(19) 0.90950(13) 0.0404(4) Uani 1 1 d . . . . .
C7 C 0.1982(2) 0.33440(19) 0.87561(13) 0.0284(4) Uani 1 1 d . . . . .
Cl8 Cl 0.09785(6) 0.45803(6) 0.90724(4) 0.04306(17) Uani 1 1 d . . . . .
C9 C 0.17496(19) 0.32355(19) 0.76870(13) 0.0267(4) Uani 1 1 d . . . . .
N10 N 0.13398(19) 0.21219(17) 0.71615(12) 0.0357(4) Uani 1 1 d . . . . .
N11 N 0.1228(2) 0.2501(2) 0.62313(13) 0.0421(4) Uani 1 1 d . . . . .
N12 N 0.15615(19) 0.37929(19) 0.61879(12) 0.0372(4) Uani 1 1 d . . . . .
N13 N 0.19017(17) 0.42794(16) 0.71146(11) 0.0275(4) Uani 1 1 d . . . . .
N14 N 0.23357(17) 0.55835(16) 0.74621(11) 0.0287(4) Uani 1 1 d . . . . .
C15 C 0.2651(2) 0.6459(2) 0.68873(14) 0.0291(4) Uani 1 1 d . . . . .
N16 N 0.2625(2) 0.6350(2) 0.59694(14) 0.0452(5) Uani 1 1 d . . . . .
H16A H 0.237(3) 0.564(3) 0.566(2) 0.054 Uiso 1 1 d . U . . .
H16B H 0.295(3) 0.703(3) 0.5727(19) 0.054 Uiso 1 1 d . U . . .
C17 C 0.3140(2) 0.7833(2) 0.74046(15) 0.0309(4) Uani 1 1 d . . . . .
Cl18 Cl 0.26946(6) 0.92549(6) 0.66459(5) 0.04811(18) Uani 1 1 d . . . . .
N19 N 0.2564(2) 0.79902(18) 0.82757(14) 0.0384(4) Uani 1 1 d . . . . .
O20 O 0.14399(18) 0.8473(2) 0.80908(15) 0.0620(5) Uani 1 1 d . . . . .
O21 O 0.3289(2) 0.7592(2) 0.90615(13) 0.0591(5) Uani 1 1 d . . . . .
N22 N 0.47234(19) 0.78150(19) 0.78747(13) 0.0386(4) Uani 1 1 d . . . . .
O23 O 0.52809(18) 0.6801(2) 0.77871(15) 0.0614(5) Uani 1 1 d . . . . .
O24 O 0.52009(19) 0.8897(2) 0.82547(17) 0.0722(6) Uani 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0384(9) 0.0858(14) 0.0522(10) -0.0050(9) 0.0145(8) -0.0021(9)
O2 0.0562(12) 0.0951(15) 0.0417(10) -0.0228(10) 0.0033(8) -0.0065(11)
N3 0.0352(9) 0.0358(9) 0.0275(9) -0.0004(7) 0.0075(7) -0.0016(7)
O4 0.0773(13) 0.0373(9) 0.0645(12) 0.0174(8) 0.0224(10) 0.0101(9)
O5 0.0599(12) 0.0662(12) 0.0551(11) 0.0099(9) 0.0139(9) -0.0319(10)
N6 0.0568(12) 0.0348(10) 0.0292(9) 0.0041(7) 0.0126(8) -0.0105(9)
C7 0.0332(10) 0.0257(9) 0.0266(9) 0.0013(7) 0.0097(8) -0.0045(8)
Cl8 0.0476(3) 0.0468(3) 0.0400(3) -0.0031(2) 0.0210(2) 0.0074(2)
C9 0.0297(10) 0.0227(9) 0.0276(9) -0.0005(7) 0.0085(8) -0.0011(7)
N10 0.0470(11) 0.0256(8) 0.0346(9) -0.0052(7) 0.0127(8) -0.0038(7)
N11 0.0579(12) 0.0349(10) 0.0332(10) -0.0105(8) 0.0136(8) -0.0065(9)
N12 0.0508(11) 0.0376(10) 0.0239(8) -0.0060(7) 0.0126(8) -0.0047(8)
N13 0.0368(9) 0.0246(8) 0.0214(8) -0.0025(6) 0.0094(7) -0.0028(7)
N14 0.0399(9) 0.0218(8) 0.0246(8) -0.0020(6) 0.0105(7) -0.0053(7)
C15 0.0331(10) 0.0255(9) 0.0305(10) 0.0020(8) 0.0127(8) 0.0026(8)
N16 0.0741(14) 0.0337(10) 0.0353(10) 0.0025(8) 0.0280(10) -0.0066(10)
C17 0.0319(10) 0.0251(9) 0.0390(11) 0.0035(8) 0.0159(8) -0.0006(8)
Cl18 0.0509(3) 0.0271(3) 0.0650(4) 0.0149(2) 0.0159(3) 0.0029(2)
N19 0.0442(11) 0.0300(9) 0.0462(12) -0.0118(8) 0.0219(9) -0.0084(8)
O20 0.0435(10) 0.0715(13) 0.0798(13) -0.0208(10) 0.0322(9) -0.0007(9)
O21 0.0755(13) 0.0666(12) 0.0398(10) -0.0050(8) 0.0247(9) 0.0007(10)
N22 0.0362(10) 0.0366(10) 0.0457(11) 0.0012(8) 0.0165(8) -0.0066(8)
O23 0.0427(10) 0.0575(12) 0.0814(14) 0.0060(9) 0.0154(9) 0.0139(9)
O24 0.0467(11) 0.0565(12) 0.1017(16) -0.0137(11) 0.0057(10) -0.0145(9)

_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
O1 N3 1.191(2) . ?
O2 N3 1.190(2) . ?
N3 C7 1.565(3) . ?
O4 N6 1.203(3) . ?
O5 N6 1.200(3) . ?
N6 C7 1.564(2) . ?
C7 C9 1.486(3) . ?
C7 Cl8 1.727(2) . ?
C9 N10 1.306(2) . ?
C9 N13 1.339(2) . ?
N10 N11 1.358(2) . ?
N11 N12 1.298(3) . ?
N12 N13 1.354(2) . ?
N13 N14 1.375(2) . ?
N14 C15 1.291(2) . ?
C15 N16 1.318(3) . ?
C15 C17 1.526(3) . ?
N16 H16A 0.81(3) . ?
N16 H16B 0.86(3) . ?
C17 N19 1.550(3) . ?
C17 N22 1.562(3) . ?
C17 Cl18 1.724(2) . ?
N19 O20 1.200(3) . ?
N19 O21 1.210(3) . ?
N22 O23 1.160(2) . ?
N22 O24 1.209(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 N3 O1 128.90(19) . . ?
O2 N3 C7 115.98(17) . . ?
O1 N3 C7 115.08(16) . . ?
O5 N6 O4 128.1(2) . . ?
O5 N6 C7 116.00(19) . . ?
O4 N6 C7 115.85(18) . . ?
C9 C7 N6 106.00(14) . . ?
C9 C7 N3 111.32(15) . . ?
N6 C7 N3 105.07(15) . . ?
C9 C7 Cl8 113.74(13) . . ?
N6 C7 Cl8 110.35(13) . . ?
N3 C7 Cl8 109.93(13) . . ?
N10 C9 N13 109.79(16) . . ?
N10 C9 C7 125.30(17) . . ?
N13 C9 C7 124.89(16) . . ?
C9 N10 N11 105.34(16) . . ?
N12 N11 N10 111.21(15) . . ?
N11 N12 N13 106.05(15) . . ?
C9 N13 N12 107.60(15) . . ?
C9 N13 N14 123.28(15) . . ?
N12 N13 N14 129.12(15) . . ?
C15 N14 N13 118.78(16) . . ?
N14 C15 N16 131.27(19) . . ?
N14 C15 C17 111.36(16) . . ?
N16 C15 C17 117.37(18) . . ?
C15 N16 H16A 121(2) . . ?
C15 N16 H16B 117.2(18) . . ?
H16A N16 H16B 122(3) . . ?
C15 C17 N19 109.17(15) . . ?
C15 C17 N22 110.24(15) . . ?
N19 C17 N22 105.03(16) . . ?
C15 C17 Cl18 113.36(14) . . ?
N19 C17 Cl18 109.95(13) . . ?
N22 C17 Cl18 108.77(13) . . ?
O20 N19 O21 127.3(2) . . ?
O20 N19 C17 116.24(19) . . ?
O21 N19 C17 116.46(19) . . ?
O23 N22 O24 129.0(2) . . ?
O23 N22 C17 116.64(18) . . ?
O24 N22 C17 114.33(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
O5 N6 C7 C9 -83.1(2) . . . . ?
O4 N6 C7 C9 94.9(2) . . . . ?
O5 N6 C7 N3 158.97(18) . . . . ?
O4 N6 C7 N3 -23.1(2) . . . . ?
O5 N6 C7 Cl8 40.5(2) . . . . ?
O4 N6 C7 Cl8 -141.57(17) . . . . ?
O2 N3 C7 C9 164.68(19) . . . . ?
O1 N3 C7 C9 -17.4(2) . . . . ?
O2 N3 C7 N6 -81.0(2) . . . . ?
O1 N3 C7 N6 96.9(2) . . . . ?
O2 N3 C7 Cl8 37.7(2) . . . . ?
O1 N3 C7 Cl8 -144.33(17) . . . . ?
N6 C7 C9 N10 1.4(3) . . . . ?
N3 C7 C9 N10 115.2(2) . . . . ?
Cl8 C7 C9 N10 -119.99(19) . . . . ?
N6 C7 C9 N13 179.87(18) . . . . ?
N3 C7 C9 N13 -66.4(2) . . . . ?
Cl8 C7 C9 N13 58.4(2) . . . . ?
N13 C9 N10 N11 -0.4(2) . . . . ?
C7 C9 N10 N11 178.21(18) . . . . ?
C9 N10 N11 N12 0.3(2) . . . . ?
N10 N11 N12 N13 -0.1(2) . . . . ?
N10 C9 N13 N12 0.4(2) . . . . ?
C7 C9 N13 N12 -178.24(17) . . . . ?
N10 C9 N13 N14 -179.39(17) . . . . ?
C7 C9 N13 N14 2.0(3) . . . . ?
N11 N12 N13 C9 -0.2(2) . . . . ?
N11 N12 N13 N14 179.58(19) . . . . ?
C9 N13 N14 C15 169.57(18) . . . . ?
N12 N13 N14 C15 -10.2(3) . . . . ?
N13 N14 C15 N16 0.8(3) . . . . ?
N13 N14 C15 C17 -178.65(16) . . . . ?
N14 C15 C17 N19 -23.3(2) . . . . ?
N16 C15 C17 N19 157.19(19) . . . . ?
N14 C15 C17 N22 91.60(19) . . . . ?
N16 C15 C17 N22 -87.9(2) . . . . ?
N14 C15 C17 Cl18 -146.21(15) . . . . ?
N16 C15 C17 Cl18 34.3(2) . . . . ?
C15 C17 N19 O20 -85.4(2) . . . . ?
N22 C17 N19 O20 156.45(18) . . . . ?
Cl18 C17 N19 O20 39.6(2) . . . . ?
C15 C17 N19 O21 93.4(2) . . . . ?
N22 C17 N19 O21 -24.8(2) . . . . ?
Cl18 C17 N19 O21 -141.62(17) . . . . ?
C15 C17 N22 O23 -1.4(2) . . . . ?
N19 C17 N22 O23 116.1(2) . . . . ?
Cl18 C17 N22 O23 -126.25(19) . . . . ?
C15 C17 N22 O24 176.20(19) . . . . ?
N19 C17 N22 O24 -66.3(2) . . . . ?
Cl18 C17 N22 O24 51.3(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
N16 H16A O4 0.81(3) 2.56(3) 3.280(3) 148(3) 4_565
N16 H16A N12 0.81(3) 2.19(3) 2.753(3) 126(2) .
N16 H16B O21 0.86(3) 2.55(3) 3.194(2) 132(2) 4_575

_refine_diff_density_max         0.511
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.050


# start Validation Reply Form

_vrf_PLAT015_shrv333             
;
PROBLEM: No _shelx_hkl_file record in SHELXL20xy CIF ....     Please Do ! 
RESPONSE: It is our policy to routinely not supply the HKL file unless 
specifically required.

;
# end Validation Reply Form
