# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1011866'
_audit_update_record             
;
2014-07-02 deposited with the CCDC.
2015-03-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H13 Cl N2 O5'
_chemical_formula_weight         240.64

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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                   6.6726(13)
_cell_length_b                   19.552(4)
_cell_length_c                   8.2906(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.50(3)
_cell_angle_gamma                90.00
_cell_volume                     1074.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      3.23
_cell_measurement_theta_max      27.48

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504
_exptl_absorpt_coefficient_mu    0.360
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.931
_exptl_absorpt_correction_T_max  0.931
_exptl_absorpt_process_details   'CrystalClear (Rigaku, 2005)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'Mercury2 (2x2 bin mode)'
_diffrn_measurement_method       CCD_Profile_fitting
_diffrn_detector_area_resol_mean 13.6612
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10975
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_sigmaI/netI    0.0252
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.23
_diffrn_reflns_theta_max         27.48
_reflns_number_total             2470
_reflns_number_gt                2058
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'PRPKAPPA (Ferguson, 1999)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0909P)²+0.6387P] 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     SHELXL
_refine_ls_extinction_coef       0.145(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2470
_refine_ls_number_parameters     137
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0731
_refine_ls_R_factor_gt           0.0637
_refine_ls_wR_factor_ref         0.1751
_refine_ls_wR_factor_gt          0.1679
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_restrained_S_all      1.116
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.41362(10) 0.11723(3) 0.67487(7) 0.0436(3) Uani 1 1 d . . .
N1 N 0.7749(3) 0.13600(10) 0.2324(2) 0.0309(4) Uani 1 1 d . . .
O5 O 1.1226(3) 0.07539(11) 0.1089(3) 0.0529(6) Uani 1 1 d . . .
C1 C 0.8502(4) 0.15785(13) 0.0747(3) 0.0398(6) Uani 1 1 d . . .
H1A H 0.7371 0.1729 -0.0008 0.048 Uiso 1 1 calc R . .
H1B H 0.9422 0.1961 0.0951 0.048 Uiso 1 1 calc R . .
C5 C 0.6038(4) 0.08599(14) 0.2054(4) 0.0465(6) Uani 1 1 d . . .
H5A H 0.5610 0.0733 0.3080 0.070 Uiso 1 1 calc R . .
H5B H 0.6477 0.0460 0.1522 0.070 Uiso 1 1 calc R . .
H5C H 0.4933 0.1067 0.1386 0.070 Uiso 1 1 calc R . .
O3 O 0.3714(4) 0.16946(12) 0.5538(3) 0.0692(7) Uani 1 1 d . . .
C2 C 0.9569(5) 0.09967(16) 0.0004(4) 0.0503(7) Uani 1 1 d . . .
H2A H 0.8624 0.0626 -0.0262 0.060 Uiso 1 1 calc R . .
H2B H 1.0054 0.1151 -0.0994 0.060 Uiso 1 1 calc R . .
C4 C 0.9508(4) 0.10548(16) 0.3403(3) 0.0454(6) Uani 1 1 d . . .
H4A H 1.0472 0.1412 0.3742 0.055 Uiso 1 1 calc R . .
H4B H 0.9026 0.0865 0.4369 0.055 Uiso 1 1 calc R . .
C3 C 1.0537(4) 0.05030(16) 0.2536(4) 0.0509(7) Uani 1 1 d . . .
H3A H 1.1673 0.0327 0.3248 0.061 Uiso 1 1 calc R . .
H3B H 0.9601 0.0129 0.2272 0.061 Uiso 1 1 calc R . .
C6 C 0.7081(4) 0.19809(14) 0.3202(3) 0.0456(6) Uani 1 1 d . . .
H6A H 0.6844 0.1852 0.4295 0.055 Uiso 1 1 calc R . .
H6B H 0.8147 0.2321 0.3284 0.055 Uiso 1 1 calc R . .
C7 C 0.5233(5) 0.22807(16) 0.2363(4) 0.0569(8) Uani 1 1 d . . .
O4 O 0.6038(5) 0.08768(18) 0.6576(4) 0.0967(10) Uani 1 1 d . . .
N2 N 0.3802(6) 0.2517(2) 0.1767(4) 0.0899(12) Uani 1 1 d . . .
O2 O 0.2533(5) 0.06958(15) 0.6534(4) 0.0991(11) Uani 1 1 d . . .
O1 O 0.4177(5) 0.1501(2) 0.8281(3) 0.1051(12) 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
Cl1 0.0437(4) 0.0491(4) 0.0379(4) 0.0035(2) 0.0036(2) -0.0014(3)
N1 0.0292(9) 0.0336(9) 0.0295(9) 0.0012(7) 0.0016(7) -0.0004(7)
O5 0.0358(10) 0.0602(12) 0.0654(13) 0.0056(10) 0.0176(9) 0.0076(9)
C1 0.0436(13) 0.0410(13) 0.0358(12) 0.0068(10) 0.0083(10) 0.0010(10)
C5 0.0307(13) 0.0484(15) 0.0608(17) 0.0001(13) 0.0066(11) -0.0073(11)
O3 0.0744(16) 0.0623(14) 0.0702(15) 0.0209(11) 0.0050(12) -0.0065(12)
C2 0.0528(17) 0.0562(16) 0.0442(15) 0.0012(12) 0.0154(12) 0.0072(13)
C4 0.0347(13) 0.0613(16) 0.0386(13) 0.0080(12) -0.0031(10) 0.0072(12)
C3 0.0373(14) 0.0540(16) 0.0618(17) 0.0145(14) 0.0073(12) 0.0131(12)
C6 0.0528(15) 0.0472(14) 0.0368(12) -0.0081(11) 0.0052(11) 0.0060(12)
C7 0.075(2) 0.0516(16) 0.0454(15) 0.0007(13) 0.0116(14) 0.0234(16)
O4 0.075(2) 0.104(2) 0.113(2) 0.0075(19) 0.0180(17) 0.0384(17)
N2 0.105(3) 0.097(2) 0.066(2) 0.0057(17) 0.0028(18) 0.060(2)
O2 0.092(2) 0.0785(18) 0.120(3) 0.0380(18) -0.0201(18) -0.0369(16)
O1 0.108(2) 0.157(3) 0.0466(15) -0.0216(17) -0.0076(14) 0.029(2)

_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 O2 1.414(3) . ?
Cl1 O4 1.416(3) . ?
Cl1 O1 1.421(3) . ?
Cl1 O3 1.437(2) . ?
N1 C5 1.501(3) . ?
N1 C6 1.509(3) . ?
N1 C1 1.514(3) . ?
N1 C4 1.515(3) . ?
O5 C3 1.420(3) . ?
O5 C2 1.426(4) . ?
C1 C2 1.510(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C4 C3 1.505(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C6 C7 1.468(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 N2 1.124(4) . ?

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 Cl1 O4 113.1(2) . . ?
O2 Cl1 O1 110.3(2) . . ?
O4 Cl1 O1 110.4(2) . . ?
O2 Cl1 O3 107.14(16) . . ?
O4 Cl1 O3 109.03(18) . . ?
O1 Cl1 O3 106.60(19) . . ?
C5 N1 C6 109.6(2) . . ?
C5 N1 C1 112.11(19) . . ?
C6 N1 C1 109.56(19) . . ?
C5 N1 C4 110.9(2) . . ?
C6 N1 C4 106.45(19) . . ?
C1 N1 C4 108.08(19) . . ?
C3 O5 C2 110.2(2) . . ?
C2 C1 N1 111.0(2) . . ?
C2 C1 H1A 109.4 . . ?
N1 C1 H1A 109.4 . . ?
C2 C1 H1B 109.4 . . ?
N1 C1 H1B 109.4 . . ?
H1A C1 H1B 108.0 . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
O5 C2 C1 111.2(2) . . ?
O5 C2 H2A 109.4 . . ?
C1 C2 H2A 109.4 . . ?
O5 C2 H2B 109.4 . . ?
C1 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
C3 C4 N1 111.4(2) . . ?
C3 C4 H4A 109.3 . . ?
N1 C4 H4A 109.3 . . ?
C3 C4 H4B 109.3 . . ?
N1 C4 H4B 109.3 . . ?
H4A C4 H4B 108.0 . . ?
O5 C3 C4 111.4(2) . . ?
O5 C3 H3A 109.3 . . ?
C4 C3 H3A 109.3 . . ?
O5 C3 H3B 109.3 . . ?
C4 C3 H3B 109.3 . . ?
H3A C3 H3B 108.0 . . ?
C7 C6 N1 111.7(2) . . ?
C7 C6 H6A 109.3 . . ?
N1 C6 H6A 109.3 . . ?
C7 C6 H6B 109.3 . . ?
N1 C6 H6B 109.3 . . ?
H6A C6 H6B 107.9 . . ?
N2 C7 C6 177.8(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
C5 N1 C1 C2 -69.7(3) . . . . ?
C6 N1 C1 C2 168.5(2) . . . . ?
C4 N1 C1 C2 52.9(3) . . . . ?
C3 O5 C2 C1 61.1(3) . . . . ?
N1 C1 C2 O5 -58.2(3) . . . . ?
C5 N1 C4 C3 70.7(3) . . . . ?
C6 N1 C4 C3 -170.2(2) . . . . ?
C1 N1 C4 C3 -52.6(3) . . . . ?
C2 O5 C3 C4 -60.8(3) . . . . ?
N1 C4 C3 O5 57.6(3) . . . . ?
C5 N1 C6 C7 -53.7(3) . . . . ?
C1 N1 C6 C7 69.7(3) . . . . ?
C4 N1 C6 C7 -173.6(2) . . . . ?
N1 C6 C7 N2 148(11) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.485
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.173
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1011867'
_audit_update_record             
;
2014-07-02 deposited with the CCDC.
2015-03-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H15 Cl N2 O4'
_chemical_formula_weight         238.67

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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                   7.7088(15)
_cell_length_b                   11.933(2)
_cell_length_c                   12.458(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.94(3)
_cell_angle_gamma                90.00
_cell_volume                     1141.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      3.00
_cell_measurement_theta_max      25.00

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504
_exptl_absorpt_coefficient_mu    0.332
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.936
_exptl_absorpt_correction_T_max  0.936
_exptl_absorpt_process_details   'CrystalClear (Rigaku, 2005)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'Mercury2 (2x2 bin mode)'
_diffrn_measurement_method       CCD_Profile_fitting
_diffrn_detector_area_resol_mean 13.6612
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9546
_diffrn_reflns_av_R_equivalents  0.0499
_diffrn_reflns_av_sigmaI/netI    0.0340
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.00
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2007
_reflns_number_gt                1785
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'PRPKAPPA (Ferguson, 1999)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1348P)²+1.1698P] 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     SHELXL
_refine_ls_extinction_coef       0.075(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2007
_refine_ls_number_parameters     137
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0809
_refine_ls_R_factor_gt           0.0751
_refine_ls_wR_factor_ref         0.2191
_refine_ls_wR_factor_gt          0.2120
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.13552(11) 0.98107(8) 0.22274(7) 0.0481(4) Uani 1 1 d . . .
N1 N 0.7974(3) 0.2856(2) 0.09828(19) 0.0342(7) Uani 1 1 d . . .
C1 C 0.6612(4) 0.3570(3) 0.0355(3) 0.0402(8) Uani 1 1 d . . .
H1A H 0.5980 0.3997 0.0857 0.048 Uiso 1 1 calc R . .
H1B H 0.7189 0.4098 -0.0088 0.048 Uiso 1 1 calc R . .
C4 C 0.7060(5) 0.1978(3) 0.1627(3) 0.0458(9) Uani 1 1 d . . .
H4A H 0.7929 0.1493 0.1994 0.055 Uiso 1 1 calc R . .
H4B H 0.6443 0.2353 0.2170 0.055 Uiso 1 1 calc R . .
C6 C 0.9142(4) 0.2273(3) 0.0251(3) 0.0435(8) Uani 1 1 d . . .
H6A H 0.9988 0.1823 0.0681 0.052 Uiso 1 1 calc R . .
H6B H 0.8449 0.1774 -0.0229 0.052 Uiso 1 1 calc R . .
C7 C 1.0052(5) 0.3072(3) -0.0387(3) 0.0488(9) Uani 1 1 d . . .
C2 C 0.5335(5) 0.2882(3) -0.0357(3) 0.0546(10) Uani 1 1 d . . .
H2A H 0.5943 0.2518 -0.0911 0.066 Uiso 1 1 calc R . .
H2B H 0.4459 0.3373 -0.0709 0.066 Uiso 1 1 calc R . .
C3 C 0.5789(5) 0.1272(3) 0.0928(4) 0.0548(10) Uani 1 1 d . . .
H3A H 0.5203 0.0757 0.1379 0.066 Uiso 1 1 calc R . .
H3B H 0.6420 0.0833 0.0435 0.066 Uiso 1 1 calc R . .
N2 N 1.0805(5) 0.3679(3) -0.0884(3) 0.0705(11) Uani 1 1 d . . .
C8 C 0.4443(5) 0.1994(4) 0.0290(4) 0.0600(11) Uani 1 1 d . . .
H8A H 0.3707 0.2357 0.0779 0.072 Uiso 1 1 calc R . .
H8B H 0.3711 0.1524 -0.0197 0.072 Uiso 1 1 calc R . .
O1 O 0.1514(6) 1.1024(3) 0.2219(4) 0.1027(14) Uani 1 1 d . . .
C5 C 0.9062(6) 0.3575(4) 0.1765(3) 0.0601(11) Uani 1 1 d . . .
H5A H 0.9650 0.4135 0.1378 0.090 Uiso 1 1 calc R . .
H5B H 0.9907 0.3118 0.2172 0.090 Uiso 1 1 calc R . .
H5C H 0.8328 0.3933 0.2246 0.090 Uiso 1 1 calc R . .
O2 O 0.2691(5) 0.9381(4) 0.1632(3) 0.0902(12) Uani 1 1 d . . .
O3 O 0.1757(6) 0.9501(4) 0.3354(3) 0.0951(13) Uani 1 1 d . . .
O4 O -0.0330(5) 0.9478(4) 0.1826(4) 0.1038(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
Cl1 0.0483(6) 0.0468(6) 0.0513(7) 0.0053(4) 0.0160(4) 0.0085(3)
N1 0.0364(14) 0.0336(13) 0.0332(13) -0.0004(10) 0.0067(11) -0.0018(10)
C1 0.0394(17) 0.0346(16) 0.0479(18) 0.0084(13) 0.0111(14) 0.0067(13)
C4 0.0502(19) 0.0450(18) 0.0441(18) 0.0146(15) 0.0152(15) 0.0010(15)
C6 0.0368(17) 0.0433(18) 0.0520(19) 0.0026(15) 0.0128(15) 0.0064(14)
C7 0.0414(18) 0.056(2) 0.051(2) 0.0030(17) 0.0128(15) 0.0075(16)
C2 0.045(2) 0.065(2) 0.052(2) 0.0090(18) -0.0035(16) 0.0031(17)
C3 0.053(2) 0.0393(19) 0.075(3) 0.0077(17) 0.0189(19) -0.0094(16)
N2 0.069(2) 0.075(2) 0.073(2) 0.0168(19) 0.035(2) 0.0004(19)
C8 0.0417(19) 0.062(2) 0.076(3) -0.001(2) 0.0047(18) -0.0116(17)
O1 0.122(3) 0.053(2) 0.129(4) 0.002(2) -0.009(3) 0.0104(19)
C5 0.063(2) 0.065(3) 0.051(2) -0.0098(18) -0.0037(18) -0.016(2)
O2 0.073(2) 0.111(3) 0.088(2) -0.039(2) 0.0223(19) 0.000(2)
O3 0.107(3) 0.112(3) 0.067(2) 0.022(2) 0.015(2) -0.002(2)
O4 0.067(2) 0.114(3) 0.129(4) -0.001(3) 0.004(2) -0.008(2)

_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 O4 1.408(4) . ?
Cl1 O2 1.416(3) . ?
Cl1 O1 1.453(4) . ?
Cl1 O3 1.459(4) . ?
N1 C5 1.500(4) . ?
N1 C6 1.506(4) . ?
N1 C1 1.516(4) . ?
N1 C4 1.528(4) . ?
C1 C2 1.510(5) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C4 C3 1.510(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C6 C7 1.459(5) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 N2 1.143(5) . ?
C2 C8 1.530(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C8 1.519(6) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 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
O4 Cl1 O2 113.7(3) . . ?
O4 Cl1 O1 110.7(3) . . ?
O2 Cl1 O1 106.9(3) . . ?
O4 Cl1 O3 112.5(3) . . ?
O2 Cl1 O3 108.0(3) . . ?
O1 Cl1 O3 104.4(3) . . ?
C5 N1 C6 109.1(3) . . ?
C5 N1 C1 109.7(3) . . ?
C6 N1 C1 111.8(2) . . ?
C5 N1 C4 108.0(3) . . ?
C6 N1 C4 109.1(2) . . ?
C1 N1 C4 109.0(2) . . ?
C2 C1 N1 112.6(3) . . ?
C2 C1 H1A 109.1 . . ?
N1 C1 H1A 109.1 . . ?
C2 C1 H1B 109.1 . . ?
N1 C1 H1B 109.1 . . ?
H1A C1 H1B 107.8 . . ?
C3 C4 N1 112.7(3) . . ?
C3 C4 H4A 109.1 . . ?
N1 C4 H4A 109.1 . . ?
C3 C4 H4B 109.1 . . ?
N1 C4 H4B 109.1 . . ?
H4A C4 H4B 107.8 . . ?
C7 C6 N1 111.6(3) . . ?
C7 C6 H6A 109.3 . . ?
N1 C6 H6A 109.3 . . ?
C7 C6 H6B 109.3 . . ?
N1 C6 H6B 109.3 . . ?
H6A C6 H6B 108.0 . . ?
N2 C7 C6 178.1(4) . . ?
C1 C2 C8 111.6(3) . . ?
C1 C2 H2A 109.3 . . ?
C8 C2 H2A 109.3 . . ?
C1 C2 H2B 109.3 . . ?
C8 C2 H2B 109.3 . . ?
H2A C2 H2B 108.0 . . ?
C4 C3 C8 111.5(3) . . ?
C4 C3 H3A 109.3 . . ?
C8 C3 H3A 109.3 . . ?
C4 C3 H3B 109.3 . . ?
C8 C3 H3B 109.3 . . ?
H3A C3 H3B 108.0 . . ?
C3 C8 C2 110.5(3) . . ?
C3 C8 H8A 109.5 . . ?
C2 C8 H8A 109.5 . . ?
C3 C8 H8B 109.5 . . ?
C2 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?

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
C5 N1 C1 C2 -173.4(3) . . . . ?
C6 N1 C1 C2 65.5(3) . . . . ?
C4 N1 C1 C2 -55.3(3) . . . . ?
C5 N1 C4 C3 174.5(3) . . . . ?
C6 N1 C4 C3 -67.0(3) . . . . ?
C1 N1 C4 C3 55.4(4) . . . . ?
C5 N1 C6 C7 -62.2(4) . . . . ?
C1 N1 C6 C7 59.3(3) . . . . ?
C4 N1 C6 C7 180.0(3) . . . . ?
N1 C6 C7 N2 144(13) . . . . ?
N1 C1 C2 C8 56.0(4) . . . . ?
N1 C4 C3 C8 -56.1(4) . . . . ?
C4 C3 C8 C2 54.2(4) . . . . ?
C1 C2 C8 C3 -54.2(5) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.850
_refine_diff_density_min         -0.481
_refine_diff_density_rms         0.096
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1011869'
_audit_update_record             
;
2014-07-02 deposited with the CCDC.
2015-03-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H20 Cl N O4'
_chemical_formula_weight         241.71

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.0231(16)
_cell_length_b                   12.525(3)
_cell_length_c                   12.668(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1273.0(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      3.01
_cell_measurement_theta_max      25.00

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             520
_exptl_absorpt_coefficient_mu    0.296
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9431
_exptl_absorpt_correction_T_max  0.9431
_exptl_absorpt_process_details   'CrystalClear (Rigaku, 2005)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'Mercury2 (2x2 bin mode)'
_diffrn_measurement_method       CCD_Profile_fitting
_diffrn_detector_area_resol_mean 13.6612
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7225
_diffrn_reflns_av_R_equivalents  0.0556
_diffrn_reflns_av_sigmaI/netI    0.0623
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.01
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2243
_reflns_number_gt                1602
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'PRPKAPPA (Ferguson, 1999)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] 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     SHELXL
_refine_ls_extinction_coef       0.035(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(3)
_refine_ls_number_reflns         2243
_refine_ls_number_parameters     137
_refine_ls_number_restraints     118
_refine_ls_R_factor_all          0.1245
_refine_ls_R_factor_gt           0.1015
_refine_ls_wR_factor_ref         0.3097
_refine_ls_wR_factor_gt          0.2802
_refine_ls_goodness_of_fit_ref   1.163
_refine_ls_restrained_S_all      1.185
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.21513(12) 0.20153(7) 0.23619(7) 0.0729(2) Uani 1 1 d U . .
O4 O 0.2886(8) 0.2046(4) 0.3300(4) 0.278(2) Uani 1 1 d U . .
C1 C 0.7104(8) 1.0706(4) 0.4015(4) 0.1310(17) Uani 1 1 d U . .
H1A H 0.7666 1.0243 0.3514 0.157 Uiso 1 1 calc R . .
H1B H 0.6467 1.1224 0.3613 0.157 Uiso 1 1 calc R . .
O3 O 0.1559(6) 0.3027(3) 0.2106(5) 0.182(2) Uani 1 1 d U . .
N1 N 0.5915(4) 1.0043(2) 0.4654(3) 0.0849(10) Uani 1 1 d U . .
C4 C 0.6875(7) 0.9298(3) 0.5296(4) 0.1090(15) Uani 1 1 d U . .
H4A H 0.6110 0.8919 0.5755 0.131 Uiso 1 1 calc R . .
H4B H 0.7381 0.8776 0.4830 0.131 Uiso 1 1 calc R . .
C5 C 0.4814(7) 1.0647(3) 0.5324(4) 0.1076(16) Uani 1 1 d U . .
H5A H 0.5441 1.0958 0.5891 0.161 Uiso 1 1 calc R . .
H5B H 0.3974 1.0182 0.5608 0.161 Uiso 1 1 calc R . .
H5C H 0.4292 1.1202 0.4920 0.161 Uiso 1 1 calc R . .
C6 C 0.4956(7) 0.9535(3) 0.3737(5) 0.1154(17) Uani 1 1 d U . .
H6A H 0.4562 1.0107 0.3286 0.138 Uiso 1 1 calc R . .
H6B H 0.5742 0.9118 0.3327 0.138 Uiso 1 1 calc R . .
O1 O 0.0817(6) 0.1250(4) 0.2399(5) 0.194(2) Uani 1 1 d U . .
C3 C 0.8148(7) 0.9755(6) 0.5929(4) 0.1404(19) Uani 1 1 d U . .
H3A H 0.8789 0.9195 0.6267 0.169 Uiso 1 1 calc R . .
H3B H 0.7656 1.0197 0.6474 0.169 Uiso 1 1 calc R . .
C9 C 0.2685(7) 0.8393(4) 0.3169(5) 0.151(2) Uani 1 1 d DU . .
H9A H 0.1824 0.7955 0.3469 0.226 Uiso 1 1 calc R . .
H9B H 0.3416 0.7957 0.2751 0.226 Uiso 1 1 calc R . .
H9C H 0.2191 0.8932 0.2730 0.226 Uiso 1 1 calc R . .
C7 C 0.3586(7) 0.8875(7) 0.3971(6) 0.180(3) Uani 1 1 d DU . .
H7A H 0.3987 0.8311 0.4431 0.216 Uiso 1 1 calc R . .
H7B H 0.2808 0.9298 0.4382 0.216 Uiso 1 1 calc R . .
C2 C 0.8312(8) 1.1252(6) 0.4603(6) 0.163(2) Uani 1 1 d U . .
H2A H 0.7782 1.1757 0.5077 0.195 Uiso 1 1 calc R . .
H2B H 0.9050 1.1643 0.4136 0.195 Uiso 1 1 calc R . .
O2 O 0.3167(8) 0.1669(5) 0.1647(6) 0.272(2) Uani 1 1 d U . .
C8 C 0.9292(8) 1.0433(7) 0.5230(6) 0.174(2) Uani 1 1 d U . .
H8A H 1.0104 1.0796 0.5669 0.209 Uiso 1 1 calc R . .
H8B H 0.9891 0.9970 0.4747 0.209 Uiso 1 1 calc R . .

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
Cl1 0.0837(5) 0.0695(4) 0.0656(4) 0.0056(4) -0.0017(4) 0.0049(4)
O4 0.452(5) 0.169(3) 0.214(3) -0.049(3) -0.235(3) 0.021(5)
C1 0.194(4) 0.121(3) 0.078(3) 0.006(2) 0.016(3) -0.034(3)
O3 0.140(3) 0.123(2) 0.284(5) 0.076(3) -0.007(3) 0.040(2)
N1 0.0765(18) 0.083(2) 0.095(2) -0.0008(17) -0.0117(16) 0.0051(15)
C4 0.131(3) 0.095(3) 0.101(3) 0.015(2) 0.006(3) 0.028(2)
C5 0.123(3) 0.086(3) 0.114(3) -0.004(2) -0.006(3) 0.014(3)
C6 0.113(3) 0.111(3) 0.121(3) -0.008(3) -0.012(3) -0.001(3)
O1 0.209(3) 0.157(2) 0.216(5) 0.009(4) -0.003(4) -0.087(3)
C3 0.136(4) 0.201(4) 0.085(3) -0.024(3) -0.034(3) 0.055(4)
C9 0.128(4) 0.115(4) 0.209(6) 0.012(4) -0.062(4) -0.027(3)
C7 0.093(3) 0.249(6) 0.197(6) -0.060(6) -0.001(4) -0.052(4)
C2 0.144(4) 0.172(4) 0.172(5) -0.026(4) 0.070(3) -0.059(3)
O2 0.296(5) 0.229(5) 0.289(4) -0.075(4) 0.196(3) 0.014(4)
C8 0.091(3) 0.245(5) 0.186(5) -0.081(4) 0.015(3) 0.001(3)

_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 O2 1.293(6) . ?
Cl1 O4 1.327(5) . ?
Cl1 O3 1.392(4) . ?
Cl1 O1 1.438(5) . ?
C1 C2 1.401(9) . ?
C1 N1 1.501(6) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
N1 C5 1.440(6) . ?
N1 C4 1.458(6) . ?
N1 C6 1.531(6) . ?
C4 C3 1.419(8) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C7 1.407(8) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C3 C8 1.531(9) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C9 C7 1.386(7) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C2 C8 1.517(11) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?

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 Cl1 O4 110.9(4) . . ?
O2 Cl1 O3 110.9(4) . . ?
O4 Cl1 O3 109.5(3) . . ?
O2 Cl1 O1 105.6(4) . . ?
O4 Cl1 O1 108.7(4) . . ?
O3 Cl1 O1 111.1(3) . . ?
C2 C1 N1 115.0(5) . . ?
C2 C1 H1A 108.5 . . ?
N1 C1 H1A 108.5 . . ?
C2 C1 H1B 108.5 . . ?
N1 C1 H1B 108.5 . . ?
H1A C1 H1B 107.5 . . ?
C5 N1 C4 109.3(4) . . ?
C5 N1 C1 114.7(3) . . ?
C4 N1 C1 108.6(4) . . ?
C5 N1 C6 110.9(4) . . ?
C4 N1 C6 115.0(3) . . ?
C1 N1 C6 98.1(4) . . ?
C3 C4 N1 116.0(4) . . ?
C3 C4 H4A 108.3 . . ?
N1 C4 H4A 108.3 . . ?
C3 C4 H4B 108.3 . . ?
N1 C4 H4B 108.3 . . ?
H4A C4 H4B 107.4 . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 N1 118.5(5) . . ?
C7 C6 H6A 107.7 . . ?
N1 C6 H6A 107.7 . . ?
C7 C6 H6B 107.7 . . ?
N1 C6 H6B 107.7 . . ?
H6A C6 H6B 107.1 . . ?
C4 C3 C8 109.2(5) . . ?
C4 C3 H3A 109.8 . . ?
C8 C3 H3A 109.8 . . ?
C4 C3 H3B 109.8 . . ?
C8 C3 H3B 109.8 . . ?
H3A C3 H3B 108.3 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C9 C7 C6 120.6(7) . . ?
C9 C7 H7A 107.2 . . ?
C6 C7 H7A 107.2 . . ?
C9 C7 H7B 107.2 . . ?
C6 C7 H7B 107.2 . . ?
H7A C7 H7B 106.8 . . ?
C1 C2 C8 107.9(6) . . ?
C1 C2 H2A 110.1 . . ?
C8 C2 H2A 110.1 . . ?
C1 C2 H2B 110.1 . . ?
C8 C2 H2B 110.1 . . ?
H2A C2 H2B 108.4 . . ?
C2 C8 C3 111.5(5) . . ?
C2 C8 H8A 109.3 . . ?
C3 C8 H8A 109.3 . . ?
C2 C8 H8B 109.3 . . ?
C3 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?

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
C2 C1 N1 C5 67.0(6) . . . . ?
C2 C1 N1 C4 -55.6(6) . . . . ?
C2 C1 N1 C6 -175.5(5) . . . . ?
C5 N1 C4 C3 -73.0(5) . . . . ?
C1 N1 C4 C3 52.8(6) . . . . ?
C6 N1 C4 C3 161.5(5) . . . . ?
C5 N1 C6 C7 -55.5(6) . . . . ?
C4 N1 C6 C7 69.3(6) . . . . ?
C1 N1 C6 C7 -175.8(5) . . . . ?
N1 C4 C3 C8 -53.6(7) . . . . ?
N1 C6 C7 C9 -179.7(6) . . . . ?
N1 C1 C2 C8 58.0(7) . . . . ?
C1 C2 C8 C3 -56.4(8) . . . . ?
C4 C3 C8 C2 54.0(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.525
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.088
