# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_11

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H15 Cl N2, 2(Cl O4)'
_chemical_formula_sum            'C7 H15 Cl3 N2 O8'
_chemical_formula_weight         361.56

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 b c a '
_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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.585(4)
_cell_length_b                   12.926(4)
_cell_length_c                   16.012(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2811.8(16)
_cell_formula_units_Z            8
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.708
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1488
_exptl_absorpt_coefficient_mu    0.689
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8199
_exptl_absorpt_correction_T_max  0.8744
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      291(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19982
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_sigmaI/netI    0.0142
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.52
_diffrn_reflns_theta_max         25.68
_reflns_number_total             2668
_reflns_number_gt                2291
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0903P)²+10.9042P] 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         2668
_refine_ls_number_parameters     218
_refine_ls_number_restraints     132
_refine_ls_R_factor_all          0.0770
_refine_ls_R_factor_gt           0.0690
_refine_ls_wR_factor_ref         0.1833
_refine_ls_wR_factor_gt          0.1744
_refine_ls_goodness_of_fit_ref   0.956
_refine_ls_restrained_S_all      0.990
_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
C1 C 0.3841(3) 0.2286(3) 0.1973(3) 0.0425(10) Uani 1 1 d . . .
H1A H 0.3303 0.1834 0.1813 0.051 Uiso 1 1 calc R . .
H1B H 0.4269 0.1906 0.2349 0.051 Uiso 1 1 calc R . .
C3 C 0.5256(3) 0.3292(4) 0.1472(3) 0.0507(11) Uani 1 1 d . . .
H3A H 0.5700 0.2908 0.1831 0.061 Uiso 1 1 calc R . .
H3B H 0.5621 0.3518 0.0985 0.061 Uiso 1 1 calc R . .
C4 C 0.4858(4) 0.4222(4) 0.1935(3) 0.0565(12) Uani 1 1 d . . .
H4A H 0.5113 0.4229 0.2501 0.068 Uiso 1 1 calc R . .
H4B H 0.5068 0.4852 0.1659 0.068 Uiso 1 1 calc R . .
C6 C 0.3741(3) 0.3211(4) 0.0637(3) 0.0465(11) Uani 1 1 d . . .
H6A H 0.4099 0.3425 0.0143 0.056 Uiso 1 1 calc R . .
H6B H 0.3194 0.2780 0.0462 0.056 Uiso 1 1 calc R . .
C7 C 0.3357(4) 0.4151(4) 0.1091(3) 0.0483(11) Uani 1 1 d . . .
H7A H 0.3552 0.4773 0.0795 0.058 Uiso 1 1 calc R . .
H7B H 0.2644 0.4129 0.1112 0.058 Uiso 1 1 calc R . .
C8 C 0.3441(4) 0.3223(3) 0.2410(3) 0.0529(12) Uani 1 1 d . . .
H8A H 0.2728 0.3192 0.2425 0.063 Uiso 1 1 calc R . .
H8B H 0.3681 0.3244 0.2980 0.063 Uiso 1 1 calc R . .
C9 C 0.4854(4) 0.1678(4) 0.0773(3) 0.0556(12) Uani 1 1 d . . .
H9A H 0.5282 0.1315 0.1160 0.067 Uiso 1 1 calc R . .
H9B H 0.5252 0.1910 0.0307 0.067 Uiso 1 1 calc R . .
Cl1 Cl 0.09253(8) 0.20828(9) 0.12406(7) 0.0445(3) Uani 1 1 d U . .
Cl2 Cl 0.25622(7) 0.05388(8) 0.35773(6) 0.0395(3) Uani 1 1 d . . .
Cl3 Cl 0.39535(14) 0.08298(14) 0.04114(14) 0.0994(7) Uani 1 1 d . . .
N1 N 0.4412(2) 0.2603(3) 0.12048(19) 0.0345(7) Uani 1 1 d . . .
N2 N 0.3763(3) 0.4170(3) 0.1953(2) 0.0398(8) Uani 1 1 d . . .
H2A H 0.3527 0.4737 0.2223 0.048 Uiso 1 1 calc R . .
O1 O 0.1441(6) 0.1813(7) 0.0529(5) 0.104(2) Uani 0.700(7) 1 d PU A 1
O2 O 0.1381(6) 0.1562(6) 0.1905(5) 0.0814(19) Uani 0.700(7) 1 d PU A 1
O3 O 0.1005(6) 0.3134(6) 0.1431(5) 0.093(2) Uani 0.700(7) 1 d PU A 1
O4 O -0.0032(6) 0.1796(7) 0.1137(5) 0.096(2) Uani 0.700(7) 1 d PU A 1
O1' O -0.0023(13) 0.2675(15) 0.1242(10) 0.092(4) Uani 0.300(7) 1 d PU A 2
O2' O 0.0917(11) 0.1474(11) 0.2034(9) 0.062(3) Uani 0.300(7) 1 d PU A 2
O3' O 0.1619(14) 0.2468(19) 0.0622(13) 0.108(5) Uani 0.300(7) 1 d PU A 2
O4' O 0.0461(13) 0.1326(13) 0.0632(10) 0.087(4) Uani 0.300(7) 1 d PU A 2
O5 O 0.3016(3) 0.0206(3) 0.2807(2) 0.0602(9) Uani 1 1 d . . .
O6 O 0.2597(3) 0.1638(3) 0.3634(3) 0.0767(12) Uani 1 1 d . . .
O7 O 0.3062(3) 0.0079(3) 0.4260(2) 0.0752(12) Uani 1 1 d . . .
O8 O 0.1551(2) 0.0204(3) 0.3550(2) 0.0567(9) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C8 1.501(6) . ?
C1 N1 1.510(5) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C3 C4 1.512(7) . ?
C3 N1 1.514(6) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 N2 1.489(6) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C6 C7 1.508(6) . ?
C6 N1 1.508(5) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 N2 1.487(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 N2 1.491(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 N1 1.507(6) . ?
C9 Cl3 1.742(6) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
Cl1 O4 1.363(8) . ?
Cl1 O1 1.382(8) . ?
Cl1 O3 1.397(8) . ?
Cl1 O2 1.402(7) . ?
Cl1 O3' 1.46(2) . ?
Cl1 O2' 1.494(14) . ?
Cl1 O1' 1.498(18) . ?
Cl1 O4' 1.518(16) . ?
Cl2 O7 1.418(4) . ?
Cl2 O6 1.424(4) . ?
Cl2 O8 1.441(3) . ?
Cl2 O5 1.445(3) . ?
N2 H2A 0.9100 . ?

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
C8 C1 N1 110.2(3) . . ?
C8 C1 H1A 109.6 . . ?
N1 C1 H1A 109.6 . . ?
C8 C1 H1B 109.6 . . ?
N1 C1 H1B 109.6 . . ?
H1A C1 H1B 108.1 . . ?
C4 C3 N1 109.6(3) . . ?
C4 C3 H3A 109.7 . . ?
N1 C3 H3A 109.7 . . ?
C4 C3 H3B 109.7 . . ?
N1 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
N2 C4 C3 109.2(4) . . ?
N2 C4 H4A 109.8 . . ?
C3 C4 H4A 109.8 . . ?
N2 C4 H4B 109.8 . . ?
C3 C4 H4B 109.8 . . ?
H4A C4 H4B 108.3 . . ?
C7 C6 N1 109.8(3) . . ?
C7 C6 H6A 109.7 . . ?
N1 C6 H6A 109.7 . . ?
C7 C6 H6B 109.7 . . ?
N1 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
N2 C7 C6 109.4(3) . . ?
N2 C7 H7A 109.8 . . ?
C6 C7 H7A 109.8 . . ?
N2 C7 H7B 109.8 . . ?
C6 C7 H7B 109.8 . . ?
H7A C7 H7B 108.2 . . ?
N2 C8 C1 109.1(3) . . ?
N2 C8 H8A 109.9 . . ?
C1 C8 H8A 109.9 . . ?
N2 C8 H8B 109.9 . . ?
C1 C8 H8B 109.9 . . ?
H8A C8 H8B 108.3 . . ?
N1 C9 Cl3 111.8(3) . . ?
N1 C9 H9A 109.2 . . ?
Cl3 C9 H9A 109.2 . . ?
N1 C9 H9B 109.2 . . ?
Cl3 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
O4 Cl1 O1 108.4(5) . . ?
O4 Cl1 O3 111.4(5) . . ?
O1 Cl1 O3 112.7(5) . . ?
O4 Cl1 O2 112.5(5) . . ?
O1 Cl1 O2 106.3(5) . . ?
O3 Cl1 O2 105.5(4) . . ?
O4 Cl1 O3' 129.0(9) . . ?
O1 Cl1 O3' 36.6(8) . . ?
O3 Cl1 O3' 76.4(10) . . ?
O2 Cl1 O3' 113.2(9) . . ?
O4 Cl1 O2' 87.3(7) . . ?
O1 Cl1 O2' 124.9(7) . . ?
O3 Cl1 O2' 109.1(6) . . ?
O2 Cl1 O2' 26.6(5) . . ?
O3' Cl1 O2' 139.8(10) . . ?
O4 Cl1 O1' 47.1(7) . . ?
O1 Cl1 O1' 124.5(7) . . ?
O3 Cl1 O1' 64.5(8) . . ?
O2 Cl1 O1' 128.5(7) . . ?
O3' Cl1 O1' 112.5(11) . . ?
O2' Cl1 O1' 105.1(8) . . ?
O4 Cl1 O4' 49.5(7) . . ?
O1 Cl1 O4' 61.2(7) . . ?
O3 Cl1 O4' 143.0(7) . . ?
O2 Cl1 O4' 111.2(7) . . ?
O3' Cl1 O4' 93.0(11) . . ?
O2' Cl1 O4' 101.7(9) . . ?
O1' Cl1 O4' 88.5(9) . . ?
O7 Cl2 O6 110.7(3) . . ?
O7 Cl2 O8 110.7(2) . . ?
O6 Cl2 O8 109.5(2) . . ?
O7 Cl2 O5 109.2(2) . . ?
O6 Cl2 O5 109.7(2) . . ?
O8 Cl2 O5 107.0(2) . . ?
C9 N1 C6 112.3(3) . . ?
C9 N1 C1 111.2(3) . . ?
C6 N1 C1 108.8(3) . . ?
C9 N1 C3 107.1(3) . . ?
C6 N1 C3 108.7(3) . . ?
C1 N1 C3 108.6(3) . . ?
C7 N2 C4 110.7(4) . . ?
C7 N2 C8 109.5(4) . . ?
C4 N2 C8 109.8(4) . . ?
C7 N2 H2A 108.9 . . ?
C4 N2 H2A 108.9 . . ?
C8 N2 H2A 108.9 . . ?

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
N1 C3 C4 N2 -1.8(5) . . . . ?
N1 C6 C7 N2 -0.2(5) . . . . ?
N1 C1 C8 N2 -1.6(5) . . . . ?
Cl3 C9 N1 C6 -59.3(4) . . . . ?
Cl3 C9 N1 C1 62.8(4) . . . . ?
Cl3 C9 N1 C3 -178.7(3) . . . . ?
C7 C6 N1 C9 -177.5(4) . . . . ?
C7 C6 N1 C1 58.9(5) . . . . ?
C7 C6 N1 C3 -59.1(5) . . . . ?
C8 C1 N1 C9 177.8(4) . . . . ?
C8 C1 N1 C6 -58.0(5) . . . . ?
C8 C1 N1 C3 60.2(5) . . . . ?
C4 C3 N1 C9 -178.2(4) . . . . ?
C4 C3 N1 C6 60.3(5) . . . . ?
C4 C3 N1 C1 -58.0(5) . . . . ?
C6 C7 N2 C4 60.5(5) . . . . ?
C6 C7 N2 C8 -60.8(5) . . . . ?
C3 C4 N2 C7 -59.1(5) . . . . ?
C3 C4 N2 C8 61.9(5) . . . . ?
C1 C8 N2 C7 61.8(5) . . . . ?
C1 C8 N2 C4 -60.0(5) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.68
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.852
_refine_diff_density_min         -0.716
_refine_diff_density_rms         0.107
_database_code_depnum_ccdc_archive 'CCDC 952878'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_111

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H15 Cl N2,2(Cl O4)'
_chemical_formula_sum            'C7 H15 Cl3 N2 O8'
_chemical_formula_weight         361.56

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/c  '
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   12.659(4)
_cell_length_b                   16.121(5)
_cell_length_c                   13.197(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.231(4)
_cell_angle_gamma                90.00
_cell_volume                     2692.5(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.784
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1488
_exptl_absorpt_coefficient_mu    0.720
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8130
_exptl_absorpt_correction_T_max  0.8694
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19033
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_av_sigmaI/netI    0.0394
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.61
_diffrn_reflns_theta_max         25.68
_reflns_number_total             5024
_reflns_number_gt                4397
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0622P)²+44.2988P] 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         5024
_refine_ls_number_parameters     362
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0969
_refine_ls_R_factor_gt           0.0883
_refine_ls_wR_factor_ref         0.2178
_refine_ls_wR_factor_gt          0.2124
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.063
_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 0.94141(12) 0.14330(8) 0.25313(12) 0.0140(3) Uani 1 1 d . . .
Cl2 Cl 0.78549(12) 0.12425(9) 0.58768(12) 0.0152(3) Uani 1 1 d . . .
Cl3 Cl 0.28958(12) 0.12860(9) 0.91337(12) 0.0171(4) Uani 1 1 d . . .
Cl4 Cl 0.44597(12) 0.14090(9) 0.24739(12) 0.0154(3) Uani 1 1 d . . .
Cl5 Cl 0.41260(14) 0.03377(12) 0.60231(15) 0.0295(4) Uani 1 1 d . . .
Cl6 Cl 0.91321(14) 0.02905(12) 0.88292(15) 0.0300(4) Uani 1 1 d . . .
O1 O 0.8310(5) 0.0497(3) 0.6290(5) 0.0436(17) Uani 1 1 d . . .
O2 O 0.7911(5) 0.1224(3) 0.4807(4) 0.0397(15) Uani 1 1 d . . .
O3 O 0.6768(4) 0.1274(4) 0.6147(5) 0.0396(15) Uani 1 1 d . . .
O4 O 0.8393(4) 0.1960(3) 0.6288(4) 0.0285(12) Uani 1 1 d . . .
O5 O 0.8282(4) 0.1367(3) 0.2508(4) 0.0255(11) Uani 1 1 d . . .
O6 O 0.9752(4) 0.2191(3) 0.3045(4) 0.0203(10) Uani 1 1 d . . .
O7 O 0.9788(4) 0.1471(3) 0.1507(4) 0.0190(10) Uani 1 1 d . . .
O8 O 0.9887(4) 0.0733(3) 0.3047(4) 0.0209(10) Uani 1 1 d U . .
O9 O 0.3328(4) 0.1306(3) 0.2441(4) 0.0263(11) Uani 1 1 d . . .
O10 O 0.4831(4) 0.1455(3) 0.3509(4) 0.0184(10) Uani 1 1 d . . .
O11 O 0.4751(4) 0.2177(3) 0.1975(4) 0.0214(10) Uani 1 1 d . . .
O12 O 0.4956(4) 0.0722(3) 0.1971(4) 0.0222(11) Uani 1 1 d . . .
O13 O 0.1815(5) 0.1466(4) 0.9304(6) 0.056(2) Uani 1 1 d . . .
O14 O 0.3399(7) 0.1039(5) 1.0038(5) 0.068(3) Uani 1 1 d . . .
O15 O 0.3420(4) 0.2024(3) 0.8768(4) 0.0263(12) Uani 1 1 d . . .
O16 O 0.2968(6) 0.0646(4) 0.8398(5) 0.0495(18) Uani 1 1 d . . .
N1 N 0.0775(4) 0.1937(3) 0.6284(4) 0.0150(11) Uani 1 1 d . . .
H1C H 0.0198 0.2214 0.6548 0.018 Uiso 1 1 calc R . .
N2 N 0.2342(4) 0.1181(3) 0.5575(4) 0.0140(11) Uani 1 1 d . . .
N3 N 0.5803(4) 0.1950(3) 0.8765(4) 0.0164(11) Uani 1 1 d . . .
H3C H 0.5214 0.2246 0.8539 0.020 Uiso 1 1 calc R . .
N4 N 0.7392(4) 0.1140(3) 0.9374(4) 0.0148(11) Uani 1 1 d . . .
C1 C 0.6773(5) 0.2355(4) 0.8372(5) 0.0193(14) Uani 1 1 d . . .
H1A H 0.6773 0.2954 0.8539 0.023 Uiso 1 1 calc R . .
H1B H 0.6798 0.2294 0.7626 0.023 Uiso 1 1 calc R . .
C2 C 0.7736(5) 0.1924(4) 0.8879(5) 0.0174(14) Uani 1 1 d . . .
H2A H 0.8270 0.1799 0.8364 0.021 Uiso 1 1 calc R . .
H2B H 0.8062 0.2298 0.9393 0.021 Uiso 1 1 calc R . .
C3 C 0.6758(5) 0.0634(4) 0.8607(5) 0.0177(13) Uani 1 1 d . . .
H3A H 0.7162 0.0571 0.7977 0.021 Uiso 1 1 calc R . .
H3B H 0.6619 0.0075 0.8883 0.021 Uiso 1 1 calc R . .
C4 C 0.5723(5) 0.1074(4) 0.8376(5) 0.0192(14) Uani 1 1 d . . .
H4A H 0.5578 0.1077 0.7636 0.023 Uiso 1 1 calc R . .
H4B H 0.5137 0.0781 0.8709 0.023 Uiso 1 1 calc R . .
C5 C 0.6696(6) 0.1345(5) 1.0260(5) 0.0245(15) Uani 1 1 d . . .
H5A H 0.7124 0.1602 1.0812 0.029 Uiso 1 1 calc R . .
H5B H 0.6372 0.0832 1.0524 0.029 Uiso 1 1 calc R . .
C6 C 0.5831(6) 0.1947(4) 0.9901(5) 0.0251(16) Uani 1 1 d . . .
H6A H 0.5138 0.1768 1.0159 0.030 Uiso 1 1 calc R . .
H6B H 0.5983 0.2511 1.0160 0.030 Uiso 1 1 calc R . .
C7 C 0.1637(5) 0.1516(4) 0.4726(5) 0.0207(14) Uani 1 1 d . . .
H7A H 0.1445 0.1063 0.4250 0.025 Uiso 1 1 calc R . .
H7B H 0.2020 0.1947 0.4346 0.025 Uiso 1 1 calc R . .
C8 C 0.0639(6) 0.1887(4) 0.5166(5) 0.0228(15) Uani 1 1 d . . .
H8A H 0.0513 0.2448 0.4882 0.027 Uiso 1 1 calc R . .
H8B H 0.0021 0.1535 0.4988 0.027 Uiso 1 1 calc R . .
C9 C 0.1693(5) 0.0597(4) 0.6192(5) 0.0160(13) Uani 1 1 d . . .
H9A H 0.2154 0.0306 0.6692 0.019 Uiso 1 1 calc R . .
H9B H 0.1359 0.0175 0.5743 0.019 Uiso 1 1 calc R . .
C10 C 0.0836(5) 0.1082(4) 0.6744(5) 0.0178(14) Uani 1 1 d . . .
H10A H 0.0146 0.0797 0.6665 0.021 Uiso 1 1 calc R . .
H10B H 0.1016 0.1121 0.7476 0.021 Uiso 1 1 calc R . .
C11 C 0.2713(5) 0.1909(4) 0.6234(5) 0.0174(13) Uani 1 1 d . . .
H11A H 0.3104 0.1699 0.6839 0.021 Uiso 1 1 calc R . .
H11B H 0.3194 0.2267 0.5846 0.021 Uiso 1 1 calc R . .
C12 C 0.1758(5) 0.2405(4) 0.6558(5) 0.0177(13) Uani 1 1 d U . .
H12A H 0.1795 0.2501 0.7299 0.021 Uiso 1 1 calc R . .
H12B H 0.1750 0.2951 0.6215 0.021 Uiso 1 1 calc R . .
C13 C 0.8326(5) 0.0659(4) 0.9800(5) 0.0210(14) Uani 1 1 d . . .
H13A H 0.8069 0.0184 1.0201 0.025 Uiso 1 1 calc R . .
H13B H 0.8748 0.1022 1.0258 0.025 Uiso 1 1 calc R . .
C14 C 0.3257(5) 0.0764(4) 0.5106(5) 0.0222(15) Uani 1 1 d . . .
H14A H 0.3644 0.1171 0.4692 0.027 Uiso 1 1 calc R . .
H14B H 0.2997 0.0318 0.4650 0.027 Uiso 1 1 calc R . .


_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 O5 1.437(5) . ?
Cl1 O8 1.442(5) . ?
Cl1 O7 1.443(5) . ?
Cl1 O6 1.457(4) . ?
Cl2 O2 1.415(6) . ?
Cl2 O3 1.430(6) . ?
Cl2 O1 1.434(5) . ?
Cl2 O4 1.443(5) . ?
Cl3 O14 1.399(7) . ?
Cl3 O16 1.421(6) . ?
Cl3 O13 1.421(7) . ?
Cl3 O15 1.450(5) . ?
Cl4 O10 1.437(5) . ?
Cl4 O9 1.441(5) . ?
Cl4 O12 1.442(5) . ?
Cl4 O11 1.454(5) . ?
Cl5 C14 1.757(7) . ?
Cl6 C13 1.758(7) . ?
N1 C8 1.484(9) . ?
N1 C12 1.494(8) . ?
N1 C10 1.506(8) . ?
N1 H1C 0.9300 . ?
N2 C14 1.486(8) . ?
N2 C9 1.501(7) . ?
N2 C7 1.518(9) . ?
N2 C11 1.528(8) . ?
N3 C1 1.493(8) . ?
N3 C6 1.498(9) . ?
N3 C4 1.505(8) . ?
N3 H3C 0.9300 . ?
N4 C2 1.492(8) . ?
N4 C13 1.513(8) . ?
N4 C5 1.516(9) . ?
N4 C3 1.516(8) . ?
C1 C2 1.543(9) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.514(9) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.530(10) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.524(10) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.535(9) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.520(9) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 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
O5 Cl1 O8 110.8(3) . . ?
O5 Cl1 O7 109.3(3) . . ?
O8 Cl1 O7 109.5(3) . . ?
O5 Cl1 O6 110.7(3) . . ?
O8 Cl1 O6 108.8(3) . . ?
O7 Cl1 O6 107.6(3) . . ?
O2 Cl2 O3 108.6(4) . . ?
O2 Cl2 O1 109.5(4) . . ?
O3 Cl2 O1 108.4(4) . . ?
O2 Cl2 O4 111.0(3) . . ?
O3 Cl2 O4 109.1(3) . . ?
O1 Cl2 O4 110.3(3) . . ?
O14 Cl3 O16 110.0(5) . . ?
O14 Cl3 O13 110.2(5) . . ?
O16 Cl3 O13 109.4(4) . . ?
O14 Cl3 O15 108.4(3) . . ?
O16 Cl3 O15 109.4(4) . . ?
O13 Cl3 O15 109.5(3) . . ?
O10 Cl4 O9 109.8(3) . . ?
O10 Cl4 O12 109.9(3) . . ?
O9 Cl4 O12 109.9(3) . . ?
O10 Cl4 O11 107.8(3) . . ?
O9 Cl4 O11 110.2(3) . . ?
O12 Cl4 O11 109.2(3) . . ?
C8 N1 C12 110.3(5) . . ?
C8 N1 C10 110.8(5) . . ?
C12 N1 C10 109.3(5) . . ?
C8 N1 H1C 108.8 . . ?
C12 N1 H1C 108.8 . . ?
C10 N1 H1C 108.8 . . ?
C14 N2 C9 112.5(5) . . ?
C14 N2 C7 107.8(5) . . ?
C9 N2 C7 107.7(5) . . ?
C14 N2 C11 110.6(5) . . ?
C9 N2 C11 109.8(5) . . ?
C7 N2 C11 108.4(5) . . ?
C1 N3 C6 110.3(5) . . ?
C1 N3 C4 110.0(5) . . ?
C6 N3 C4 109.8(5) . . ?
C1 N3 H3C 108.9 . . ?
C6 N3 H3C 108.9 . . ?
C4 N3 H3C 108.9 . . ?
C2 N4 C13 111.3(5) . . ?
C2 N4 C5 109.4(5) . . ?
C13 N4 C5 106.7(5) . . ?
C2 N4 C3 108.6(5) . . ?
C13 N4 C3 111.8(5) . . ?
C5 N4 C3 108.9(5) . . ?
N3 C1 C2 107.4(5) . . ?
N3 C1 H1A 110.2 . . ?
C2 C1 H1A 110.2 . . ?
N3 C1 H1B 110.2 . . ?
C2 C1 H1B 110.2 . . ?
H1A C1 H1B 108.5 . . ?
N4 C2 C1 109.6(5) . . ?
N4 C2 H2A 109.7 . . ?
C1 C2 H2A 109.7 . . ?
N4 C2 H2B 109.7 . . ?
C1 C2 H2B 109.7 . . ?
H2A C2 H2B 108.2 . . ?
C4 C3 N4 109.0(5) . . ?
C4 C3 H3A 109.9 . . ?
N4 C3 H3A 109.9 . . ?
C4 C3 H3B 109.9 . . ?
N4 C3 H3B 109.9 . . ?
H3A C3 H3B 108.3 . . ?
N3 C4 C3 108.6(5) . . ?
N3 C4 H4A 110.0 . . ?
C3 C4 H4A 110.0 . . ?
N3 C4 H4B 110.0 . . ?
C3 C4 H4B 110.0 . . ?
H4A C4 H4B 108.4 . . ?
N4 C5 C6 108.9(5) . . ?
N4 C5 H5A 109.9 . . ?
C6 C5 H5A 109.9 . . ?
N4 C5 H5B 109.9 . . ?
C6 C5 H5B 109.9 . . ?
H5A C5 H5B 108.3 . . ?
N3 C6 C5 108.2(5) . . ?
N3 C6 H6A 110.1 . . ?
C5 C6 H6A 110.1 . . ?
N3 C6 H6B 110.1 . . ?
C5 C6 H6B 110.1 . . ?
H6A C6 H6B 108.4 . . ?
N2 C7 C8 109.7(5) . . ?
N2 C7 H7A 109.7 . . ?
C8 C7 H7A 109.7 . . ?
N2 C7 H7B 109.7 . . ?
C8 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?
N1 C8 C7 108.7(5) . . ?
N1 C8 H8A 109.9 . . ?
C7 C8 H8A 109.9 . . ?
N1 C8 H8B 110.0 . . ?
C7 C8 H8B 109.9 . . ?
H8A C8 H8B 108.3 . . ?
N2 C9 C10 109.8(5) . . ?
N2 C9 H9A 109.7 . . ?
C10 C9 H9A 109.7 . . ?
N2 C9 H9B 109.7 . . ?
C10 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
N1 C10 C9 107.8(5) . . ?
N1 C10 H10A 110.1 . . ?
C9 C10 H10A 110.1 . . ?
N1 C10 H10B 110.1 . . ?
C9 C10 H10B 110.1 . . ?
H10A C10 H10B 108.5 . . ?
C12 C11 N2 109.2(5) . . ?
C12 C11 H11A 109.8 . . ?
N2 C11 H11A 109.8 . . ?
C12 C11 H11B 109.8 . . ?
N2 C11 H11B 109.8 . . ?
H11A C11 H11B 108.3 . . ?
N1 C12 C11 109.2(5) . . ?
N1 C12 H12A 109.8 . . ?
C11 C12 H12A 109.8 . . ?
N1 C12 H12B 109.8 . . ?
C11 C12 H12B 109.8 . . ?
H12A C12 H12B 108.3 . . ?
N4 C13 Cl6 111.3(5) . . ?
N4 C13 H13A 109.4 . . ?
Cl6 C13 H13A 109.4 . . ?
N4 C13 H13B 109.4 . . ?
Cl6 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
N2 C14 Cl5 111.8(5) . . ?
N2 C14 H14A 109.2 . . ?
Cl5 C14 H14A 109.2 . . ?
N2 C14 H14B 109.2 . . ?
Cl5 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?

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
C6 N3 C1 C2 52.8(7) . . . . ?


_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        25.68
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         1.553
_refine_diff_density_min         -0.886
_refine_diff_density_rms         0.170
_database_code_depnum_ccdc_archive 'CCDC 952879'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_111

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H15 Cl N2, 2(Cl O4)'
_chemical_formula_sum            'C7 H15 Cl3 N2 O8'
_chemical_formula_weight         361.56

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 b c a '
_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'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   13.3098(12)
_cell_length_b                   12.7949(12)
_cell_length_c                   16.0119(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2726.8(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.761
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1488
_exptl_absorpt_coefficient_mu    0.711
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8150
_exptl_absorpt_correction_T_max  0.8709
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      170(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19183
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_sigmaI/netI    0.0150
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.97
_diffrn_reflns_theta_max         25.67
_reflns_number_total             2582
_reflns_number_gt                2322
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0614P)²+7.6167P] 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         2582
_refine_ls_number_parameters     217
_refine_ls_number_restraints     48
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0560
_refine_ls_wR_factor_ref         0.1537
_refine_ls_wR_factor_gt          0.1493
_refine_ls_goodness_of_fit_ref   1.243
_refine_ls_restrained_S_all      1.246
_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 0.08976(7) 0.28856(7) 0.12603(5) 0.0246(3) Uani 1 1 d . . .
Cl2 Cl 0.25494(6) 0.44377(7) 0.35875(5) 0.0211(3) Uani 1 1 d . . .
Cl3 Cl 0.10680(10) 0.91198(10) 0.03542(9) 0.0545(4) Uani 1 1 d . . .
O1 O 0.1405(6) 0.3418(6) 0.1923(5) 0.0328(19) Uani 0.50 1 d PU A 2
O2 O -0.0171(6) 0.2934(7) 0.1224(5) 0.0456(18) Uani 0.50 1 d PU A 2
O3 O 0.1181(8) 0.1813(8) 0.1357(6) 0.063(3) Uani 0.50 1 d PU A 2
O4 O 0.1282(6) 0.3302(6) 0.0498(5) 0.0491(19) Uani 0.50 1 d PU A 2
O1' O 0.1119(6) 0.3432(7) 0.2034(5) 0.038(2) Uani 0.50 1 d PU A 1
O2' O -0.0010(7) 0.3362(8) 0.1070(6) 0.063(2) Uani 0.50 1 d PU A 1
O3' O 0.0816(7) 0.1797(7) 0.1459(6) 0.055(2) Uani 0.50 1 d PU A 1
O4' O 0.1611(6) 0.2951(7) 0.0614(5) 0.0512(19) Uani 0.50 1 d PU A 1
O5 O 0.3064(2) 0.4903(2) 0.42757(17) 0.0363(7) Uani 1 1 d . . .
O6 O 0.3027(2) 0.4753(2) 0.28153(16) 0.0314(6) Uani 1 1 d . . .
O7 O 0.1521(2) 0.4804(2) 0.35628(17) 0.0291(6) Uani 1 1 d . . .
O8 O 0.2554(3) 0.3325(2) 0.3662(2) 0.0406(8) Uani 1 1 d . . .
N1 N 0.1254(2) 0.5792(2) 0.19597(18) 0.0216(6) Uani 1 1 d . . .
H1C H 0.1500 0.5213 0.2245 0.026 Uiso 1 1 calc R . .
N2 N 0.0595(2) 0.7359(2) 0.11895(18) 0.0196(6) Uani 1 1 d . . .
C1 C 0.1176(3) 0.7697(3) 0.1951(2) 0.0261(8) Uani 1 1 d . . .
H1A H 0.1739 0.8156 0.1781 0.031 Uiso 1 1 calc R . .
H1B H 0.0732 0.8100 0.2328 0.031 Uiso 1 1 calc R . .
C2 C 0.1580(3) 0.6759(3) 0.2403(2) 0.0316(9) Uani 1 1 d . . .
H2A H 0.2323 0.6790 0.2422 0.038 Uiso 1 1 calc R . .
H2B H 0.1325 0.6750 0.2984 0.038 Uiso 1 1 calc R . .
C3 C 0.1269(3) 0.6732(3) 0.0626(2) 0.0310(9) Uani 1 1 d . . .
H3A H 0.1837 0.7171 0.0435 0.037 Uiso 1 1 calc R . .
H3B H 0.0888 0.6500 0.0128 0.037 Uiso 1 1 calc R . .
C4 C 0.1666(3) 0.5789(3) 0.1092(2) 0.0274(8) Uani 1 1 d . . .
H4A H 0.1463 0.5141 0.0801 0.033 Uiso 1 1 calc R . .
H4B H 0.2410 0.5813 0.1111 0.033 Uiso 1 1 calc R . .
C5 C -0.0267(3) 0.6674(3) 0.1473(3) 0.0325(9) Uani 1 1 d . . .
H5A H -0.0658 0.6438 0.0982 0.039 Uiso 1 1 calc R . .
H5B H -0.0720 0.7079 0.1841 0.039 Uiso 1 1 calc R . .
C6 C 0.0137(3) 0.5736(3) 0.1940(3) 0.0344(9) Uani 1 1 d . . .
H6A H -0.0130 0.5730 0.2517 0.041 Uiso 1 1 calc R . .
H6B H -0.0078 0.5085 0.1659 0.041 Uiso 1 1 calc R . .
C7 C 0.0146(3) 0.8286(3) 0.0748(3) 0.0317(9) Uani 1 1 d . . .
H7A H -0.0286 0.8678 0.1142 0.038 Uiso 1 1 calc R . .
H7B H -0.0282 0.8039 0.0282 0.038 Uiso 1 1 calc R . .


_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' 1.387(9) . ?
Cl1 O4' 1.407(8) . ?
Cl1 O2 1.425(8) . ?
Cl1 O4 1.427(8) . ?
Cl1 O1 1.430(7) . ?
Cl1 O3 1.432(10) . ?
Cl1 O3' 1.433(10) . ?
Cl1 O1' 1.453(8) . ?
Cl2 O5 1.427(3) . ?
Cl2 O8 1.429(3) . ?
Cl2 O7 1.447(3) . ?
Cl2 O6 1.448(3) . ?
Cl3 C7 1.743(4) . ?
N1 C6 1.488(5) . ?
N1 C2 1.491(5) . ?
N1 C4 1.494(4) . ?
N1 H1C 0.9300 . ?
N2 C3 1.504(5) . ?
N2 C7 1.505(5) . ?
N2 C1 1.508(4) . ?
N2 C5 1.513(5) . ?
C1 C2 1.502(5) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.514(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.513(6) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 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
O2' Cl1 O4' 113.6(5) . . ?
O2' Cl1 O2 26.2(4) . . ?
O4' Cl1 O2 129.9(5) . . ?
O2' Cl1 O4 87.7(5) . . ?
O4' Cl1 O4 26.7(4) . . ?
O2 Cl1 O4 107.9(5) . . ?
O2' Cl1 O1 111.4(5) . . ?
O4' Cl1 O1 101.5(5) . . ?
O2 Cl1 O1 118.8(4) . . ?
O4 Cl1 O1 106.7(5) . . ?
O2' Cl1 O3 132.4(6) . . ?
O4' Cl1 O3 87.6(5) . . ?
O2 Cl1 O3 108.0(5) . . ?
O4 Cl1 O3 110.9(5) . . ?
O1 Cl1 O3 104.6(5) . . ?
O2' Cl1 O3' 114.2(6) . . ?
O4' Cl1 O3' 105.8(5) . . ?
O2 Cl1 O3' 88.6(5) . . ?
O4 Cl1 O3' 125.5(5) . . ?
O1 Cl1 O3' 109.5(5) . . ?
O3 Cl1 O3' 20.6(5) . . ?
O2' Cl1 O1' 98.8(5) . . ?
O4' Cl1 O1' 117.5(5) . . ?
O2 Cl1 O1' 102.5(5) . . ?
O4 Cl1 O1' 118.5(5) . . ?
O1 Cl1 O1' 16.8(4) . . ?
O3 Cl1 O1' 108.4(5) . . ?
O3' Cl1 O1' 107.1(5) . . ?
O5 Cl2 O8 110.43(19) . . ?
O5 Cl2 O7 109.87(18) . . ?
O8 Cl2 O7 109.19(19) . . ?
O5 Cl2 O6 109.41(18) . . ?
O8 Cl2 O6 110.34(19) . . ?
O7 Cl2 O6 107.57(16) . . ?
C6 N1 C2 109.9(3) . . ?
C6 N1 C4 110.3(3) . . ?
C2 N1 C4 109.7(3) . . ?
C6 N1 H1C 109.0 . . ?
C2 N1 H1C 109.0 . . ?
C4 N1 H1C 109.0 . . ?
C3 N2 C7 112.0(3) . . ?
C3 N2 C1 109.4(3) . . ?
C7 N2 C1 110.9(3) . . ?
C3 N2 C5 108.8(3) . . ?
C7 N2 C5 107.3(3) . . ?
C1 N2 C5 108.2(3) . . ?
C2 C1 N2 110.1(3) . . ?
C2 C1 H1A 109.6 . . ?
N2 C1 H1A 109.6 . . ?
C2 C1 H1B 109.6 . . ?
N2 C1 H1B 109.6 . . ?
H1A C1 H1B 108.2 . . ?
N1 C2 C1 109.3(3) . . ?
N1 C2 H2A 109.8 . . ?
C1 C2 H2A 109.8 . . ?
N1 C2 H2B 109.8 . . ?
C1 C2 H2B 109.8 . . ?
H2A C2 H2B 108.3 . . ?
N2 C3 C4 109.7(3) . . ?
N2 C3 H3A 109.7 . . ?
C4 C3 H3A 109.7 . . ?
N2 C3 H3B 109.7 . . ?
C4 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
N1 C4 C3 109.2(3) . . ?
N1 C4 H4A 109.8 . . ?
C3 C4 H4A 109.8 . . ?
N1 C4 H4B 109.8 . . ?
C3 C4 H4B 109.8 . . ?
H4A C4 H4B 108.3 . . ?
N2 C5 C6 109.8(3) . . ?
N2 C5 H5A 109.7 . . ?
C6 C5 H5A 109.7 . . ?
N2 C5 H5B 109.7 . . ?
C6 C5 H5B 109.7 . . ?
H5A C5 H5B 108.2 . . ?
N1 C6 C5 109.1(3) . . ?
N1 C6 H6A 109.9 . . ?
C5 C6 H6A 109.9 . . ?
N1 C6 H6B 109.9 . . ?
C5 C6 H6B 109.9 . . ?
H6A C6 H6B 108.3 . . ?
N2 C7 Cl3 111.9(3) . . ?
N2 C7 H7A 109.2 . . ?
Cl3 C7 H7A 109.2 . . ?
N2 C7 H7B 109.2 . . ?
Cl3 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?

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
C3 N2 C1 C2 -58.3(4) . . . . ?


_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.67
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.149
_refine_diff_density_min         -0.772
_refine_diff_density_rms         0.094
_database_code_depnum_ccdc_archive 'CCDC 952880'
