# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_203
_database_code_depnum_ccdc_archive 'CCDC 1427895'
_audit_update_record             
;
2015-12-26 deposited with the CCDC.
2016-01-27 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 H14 N2, 2(B F4), H2 O'
_chemical_formula_sum            'C6 H16 B2 F8 N2 O'
_chemical_formula_weight         305.83

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

_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, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'

_cell_length_a                   13.0629(4)
_cell_length_b                   7.8370(2)
_cell_length_c                   11.6838(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1196.12(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    203(2)
_cell_measurement_reflns_used    6826
_cell_measurement_theta_min      5.645
_cell_measurement_theta_max      68.269

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.698
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    1.761
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      203(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8326
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         5.645
_diffrn_reflns_theta_max         68.269
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2189
_reflns_number_gt                1784
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.897
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    0.996

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0834P)²+6.6453P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.030(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.2(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1813
_refine_ls_number_parameters     217
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0884
_refine_ls_R_factor_gt           0.0873
_refine_ls_wR_factor_ref         0.2244
_refine_ls_wR_factor_gt          0.2236
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.2272(7) 0.7183(12) 0.1004(11) 0.027(2) Uani 1 1 d . . . . .
C1 C -0.0426(10) 0.254(2) 0.3363(11) 0.062(4) Uani 1 1 d . . . . .
H1A H -0.0877 0.3284 0.3814 0.074 Uiso 1 1 calc R U . . .
H1B H -0.0814 0.1529 0.3138 0.074 Uiso 1 1 calc R U . . .
C2 C -0.0057(7) 0.3489(11) 0.2304(10) 0.036(2) Uani 1 1 d . . . . .
H2A H -0.0267 0.2867 0.1615 0.043 Uiso 1 1 calc R U . . .
H2B H -0.0366 0.4628 0.2278 0.043 Uiso 1 1 calc R U . . .
C3 C 0.1153(13) 0.0933(16) 0.3381(14) 0.071(5) Uani 1 1 d . . . . .
H3A H 0.0779 -0.0088 0.3137 0.086 Uiso 1 1 calc R U . . .
H3B H 0.1732 0.0570 0.3855 0.086 Uiso 1 1 calc R U . . .
C4 C 0.1542(7) 0.1886(11) 0.2342(10) 0.034(2) Uani 1 1 d . . . . .
H4A H 0.2290 0.1974 0.2371 0.041 Uiso 1 1 calc R U . . .
H4B H 0.1353 0.1272 0.1643 0.041 Uiso 1 1 calc R U . . .
C5 C 0.1038(9) 0.3611(15) 0.4444(10) 0.045(3) Uani 1 1 d . . . . .
H5A H 0.1625 0.3283 0.4919 0.054 Uiso 1 1 calc R U . . .
H5B H 0.0585 0.4335 0.4903 0.054 Uiso 1 1 calc R U . . .
C6 C 0.1404(7) 0.4581(13) 0.3398(10) 0.037(2) Uani 1 1 d . . . . .
H6A H 0.1113 0.5733 0.3398 0.045 Uiso 1 1 calc R U . . .
H6B H 0.2152 0.4682 0.3414 0.045 Uiso 1 1 calc R U . . .
F3 F 0.1202(4) 0.6958(9) 0.1081(7) 0.0539(19) Uani 1 1 d . . . . .
F2 F 0.2727(4) 0.5694(7) 0.1401(7) 0.0481(18) Uani 1 1 d . . . . .
F1 F 0.2554(5) 0.7454(9) -0.0115(7) 0.0536(19) Uani 1 1 d . . . . .
F4 F 0.2568(6) 0.8528(8) 0.1679(8) 0.067(2) Uani 1 1 d . . . . .
B2 B 0.4098(8) 0.2389(12) 0.4217(10) 0.030(2) Uani 0.42(6) 1 d . . P A 1
F5 F 0.392(2) 0.298(3) 0.311(2) 0.019(5) Uani 0.42(6) 1 d . . P A 1
F6 F 0.338(3) 0.320(5) 0.490(3) 0.066(9) Uani 0.42(6) 1 d . . P A 1
F7 F 0.503(2) 0.281(5) 0.468(3) 0.063(9) Uani 0.42(6) 1 d . . P A 1
F8 F 0.387(2) 0.067(2) 0.436(2) 0.045(6) Uani 0.42(6) 1 d . . P A 1
B2' B 0.4098(8) 0.2389(12) 0.4217(10) 0.030(2) Uani 0.58(6) 1 d D . P A 2
F5' F 0.416(2) 0.266(4) 0.305(2) 0.055(8) Uani 0.58(6) 1 d D . P A 2
F6' F 0.374(2) 0.377(3) 0.4850(18) 0.055(6) Uani 0.58(6) 1 d D . P A 2
F7' F 0.5044(18) 0.190(5) 0.4508(18) 0.087(9) Uani 0.58(6) 1 d D . P A 2
F8' F 0.339(3) 0.108(3) 0.4377(18) 0.073(8) Uani 0.58(6) 1 d D . P A 2
N1 N 0.0471(6) 0.2040(10) 0.4056(8) 0.034(2) Uani 1 1 d . . . . .
H1 H 0.0232 0.1404 0.4737 0.041 Uiso 1 1 calc R U . . .
N2 N 0.1075(6) 0.3639(9) 0.2335(8) 0.0298(18) Uani 1 1 d . . . . .
H2 H 0.1312 0.4268 0.1650 0.036 Uiso 1 1 calc R U . . .
O1 O 0.0702(8) 0.0591(10) 0.6197(8) 0.054(2) Uani 1 1 d D . . . .
H1WB H 0.054(10) 0.140(13) 0.665(11) 0.065 Uiso 1 1 d D U . . .
H1WA H 0.118(8) 0.010(16) 0.658(11) 0.065 Uiso 1 1 d D U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 F4 1.373(13) . ?
B1 F1 1.375(15) . ?
B1 F2 1.390(11) . ?
B1 F3 1.411(11) . ?
C1 N1 1.478(16) . ?
C1 C2 1.520(18) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C2 N2 1.484(12) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C3 N1 1.472(15) . ?
C3 C4 1.514(17) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C4 N2 1.503(11) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C5 N1 1.507(13) . ?
C5 C6 1.517(15) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C6 N2 1.508(13) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
B2 F7 1.38(3) . ?
B2 F6 1.38(4) . ?
B2 F8 1.39(2) . ?
B2 F5 1.40(3) . ?
B2' F7' 1.337(16) . ?
B2' F5' 1.38(2) . ?
B2' F6' 1.390(19) . ?
B2' F8' 1.396(17) . ?
N1 H1 0.9900 . ?
N2 H2 0.9900 . ?
O1 H1WB 0.85(3) . ?
O1 H1WA 0.86(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
F4 B1 F1 110.6(9) . . ?
F4 B1 F2 109.4(8) . . ?
F1 B1 F2 109.4(9) . . ?
F4 B1 F3 109.8(9) . . ?
F1 B1 F3 110.2(8) . . ?
F2 B1 F3 107.3(7) . . ?
N1 C1 C2 108.9(10) . . ?
N1 C1 H1A 109.9 . . ?
C2 C1 H1A 109.9 . . ?
N1 C1 H1B 109.9 . . ?
C2 C1 H1B 109.9 . . ?
H1A C1 H1B 108.3 . . ?
N2 C2 C1 109.5(9) . . ?
N2 C2 H2A 109.8 . . ?
C1 C2 H2A 109.8 . . ?
N2 C2 H2B 109.8 . . ?
C1 C2 H2B 109.8 . . ?
H2A C2 H2B 108.2 . . ?
N1 C3 C4 110.0(8) . . ?
N1 C3 H3A 109.7 . . ?
C4 C3 H3A 109.7 . . ?
N1 C3 H3B 109.7 . . ?
C4 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
N2 C4 C3 108.6(8) . . ?
N2 C4 H4A 110.0 . . ?
C3 C4 H4A 110.0 . . ?
N2 C4 H4B 110.0 . . ?
C3 C4 H4B 110.0 . . ?
H4A C4 H4B 108.4 . . ?
N1 C5 C6 108.8(8) . . ?
N1 C5 H5A 109.9 . . ?
C6 C5 H5A 109.9 . . ?
N1 C5 H5B 109.9 . . ?
C6 C5 H5B 109.9 . . ?
H5A C5 H5B 108.3 . . ?
N2 C6 C5 109.2(7) . . ?
N2 C6 H6A 109.8 . . ?
C5 C6 H6A 109.8 . . ?
N2 C6 H6B 109.8 . . ?
C5 C6 H6B 109.8 . . ?
H6A C6 H6B 108.3 . . ?
F7 B2 F6 105.4(19) . . ?
F7 B2 F8 112.1(15) . . ?
F6 B2 F8 103.2(19) . . ?
F7 B2 F5 115.8(17) . . ?
F6 B2 F5 105(2) . . ?
F8 B2 F5 113.5(17) . . ?
F7' B2' F5' 104.1(17) . . ?
F7' B2' F6' 113.4(15) . . ?
F5' B2' F6' 115.0(16) . . ?
F7' B2' F8' 111.8(16) . . ?
F5' B2' F8' 106.4(16) . . ?
F6' B2' F8' 106.0(14) . . ?
C3 N1 C1 110.1(11) . . ?
C3 N1 C5 110.2(10) . . ?
C1 N1 C5 109.7(9) . . ?
C3 N1 H1 108.9 . . ?
C1 N1 H1 108.9 . . ?
C5 N1 H1 108.9 . . ?
C2 N2 C4 109.4(7) . . ?
C2 N2 C6 110.1(8) . . ?
C4 N2 C6 109.1(8) . . ?
C2 N2 H2 109.4 . . ?
C4 N2 H2 109.4 . . ?
C6 N2 H2 109.4 . . ?
H1WB O1 H1WA 100(10) . . ?

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 C1 C2 N2 -1.8(13) . . . . ?
N1 C3 C4 N2 -1.5(16) . . . . ?
N1 C5 C6 N2 0.0(12) . . . . ?
C4 C3 N1 C1 61.4(15) . . . . ?
C4 C3 N1 C5 -59.7(15) . . . . ?
C2 C1 N1 C3 -59.4(13) . . . . ?
C2 C1 N1 C5 62.1(12) . . . . ?
C6 C5 N1 C3 60.5(13) . . . . ?
C6 C5 N1 C1 -60.9(12) . . . . ?
C1 C2 N2 C4 61.0(11) . . . . ?
C1 C2 N2 C6 -58.9(10) . . . . ?
C3 C4 N2 C2 -59.0(13) . . . . ?
C3 C4 N2 C6 61.5(11) . . . . ?
C5 C6 N2 C2 59.7(10) . . . . ?
C5 C6 N2 C4 -60.4(10) . . . . ?

_refine_diff_density_max         0.370
_refine_diff_density_min         -0.448
_refine_diff_density_rms         0.103


# start Validation Reply Form
_vrf_PLAT089_203                 
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       5.32 Note  
RESPONSE: The anomalous dispersion effects of light 
atoms in non-centrosymmetric structures are insignificant.
In this structure the F atom is the heaviest 
atom and it is unwise to attempt to use unmerged 
Friedel-related reflections simply to boost the r/p ratio.
;
_vrf_PLAT340_203                 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01733 Ang.  
RESPONSE: This alert is generated because of disorders in the structure.
;
# 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_296
_database_code_depnum_ccdc_archive 'CCDC 1427896'
_audit_update_record             
;
2015-12-26 deposited with the CCDC.
2016-01-27 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 H14 N2, 2(B F4), H2 O'
_chemical_formula_sum            'C6 H16 B2 F8 N2 O'
_chemical_formula_weight         305.83

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

_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, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   13.231(10)
_cell_length_b                   7.883(7)
_cell_length_c                   11.786(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1229.3(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6680
_cell_measurement_theta_min      6.54
_cell_measurement_theta_max      68.19

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.653
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    1.714
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7954
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_av_R_equivalents  0.0195
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         6.536
_diffrn_reflns_theta_max         68.188
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.824
_diffrn_reflns_point_group_measured_fraction_full 0.828
_reflns_number_total             2255
_reflns_number_gt                1805
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.595
_reflns_Friedel_fraction_max     0.650
_reflns_Friedel_fraction_full    0.654

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0781P)²+0.2986P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.016(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 644 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1860
_refine_ls_number_parameters     218
_refine_ls_number_restraints     29
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_ref         0.1192
_refine_ls_wR_factor_gt          0.1182
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.0750(3) 0.0623(5) 1.0122(3) 0.0786(9) Uani 1 1 d . . . A 4
C1 C 0.1396(3) 0.4564(4) 0.2924(4) 0.0563(8) Uani 1 1 d . . . B 4
H1A H 0.2126 0.4664 0.2909 0.068 Uiso 1 1 calc R U . B 4
H1B H 0.1110 0.5697 0.2925 0.068 Uiso 1 1 calc R U . B 4
C2 C 0.1040(4) 0.3613(6) 0.1893(4) 0.0655(11) Uani 1 1 d . . . B 4
H2A H 0.0599 0.4329 0.1442 0.079 Uiso 1 1 calc R U . B 4
H2B H 0.1614 0.3291 0.1429 0.079 Uiso 1 1 calc R U . B 4
C3 C 0.1526(3) 0.1896(4) 0.3982(4) 0.0539(9) Uani 1 1 d . . . B 4
H3A H 0.1326 0.1302 0.4667 0.065 Uiso 1 1 calc R U . B 4
H3B H 0.2258 0.1975 0.3971 0.065 Uiso 1 1 calc R U . B 4
C4 C 0.1163(3) 0.0942(5) 0.2957(4) 0.0649(10) Uani 1 1 d . . . B 4
H4A H 0.1736 0.0592 0.2500 0.078 Uiso 1 1 calc R U . B 4
H4B H 0.0800 -0.0067 0.3192 0.078 Uiso 1 1 calc R U . B 4
C5 C -0.0056(2) 0.3493(5) 0.4005(3) 0.0529(8) Uani 1 1 d . . . B 4
H5A H -0.0356 0.4615 0.4035 0.064 Uiso 1 1 calc R U . B 4
H5B H -0.0264 0.2871 0.4675 0.064 Uiso 1 1 calc R U . B 4
C6 C -0.0404(3) 0.2576(6) 0.2950(4) 0.0599(9) Uani 1 1 d . . . B 4
H6A H -0.0792 0.1581 0.3161 0.072 Uiso 1 1 calc R U . B 4
H6B H -0.0836 0.3314 0.2505 0.072 Uiso 1 1 calc R U . B 4
B1 B 0.2263(3) 0.7188(5) 0.5311(4) 0.0468(9) Uani 1 1 d . . . C 4
H1WA H 0.131(4) -0.005(8) 1.005(7) 0.095(17) Uiso 1 1 d . . . D 4
H1WB H 0.092(4) 0.138(9) 0.958(7) 0.089(19) Uiso 1 1 d . . . E 4
N2 N 0.10730(17) 0.3633(3) 0.3970(2) 0.0427(7) Uani 1 1 d . . . B 4
H2 H 0.1305 0.4259 0.4640 0.051 Uiso 1 1 calc R U . B 4
N1 N 0.0480(2) 0.2061(4) 0.2268(3) 0.0505(7) Uani 1 1 d . . . B 4
H1 H 0.0248 0.1436 0.1599 0.061 Uiso 1 1 calc R U . B 4
F1 F 0.27109(17) 0.5689(3) 0.4935(3) 0.0734(8) Uani 1 1 d . . . C 4
F2 F 0.12298(15) 0.6978(4) 0.5225(3) 0.0759(8) Uani 1 1 d . . . C 4
F3 F 0.2584(2) 0.8482(4) 0.4620(4) 0.0937(11) Uani 1 1 d . . . C 4
F4 F 0.2534(2) 0.7471(5) 0.6408(3) 0.0953(10) Uani 1 1 d . . . C 4
B2 B 0.0908(3) 0.2366(5) 0.7106(4) 0.0478(9) Uani 0.51(2) 1 d . . P F 1
F5 F 0.1448(11) 0.340(2) 0.6459(12) 0.136(6) Uani 0.51(2) 1 d . . P F 1
F6 F -0.0063(7) 0.2514(17) 0.6771(10) 0.110(4) Uani 0.51(2) 1 d . . P F 1
F7 F 0.1138(11) 0.0759(10) 0.6916(12) 0.106(4) Uani 0.51(2) 1 d . . P F 1
F8 F 0.0913(15) 0.262(2) 0.8184(13) 0.129(7) Uani 0.51(2) 1 d . . P F 1
B2' B 0.0908(3) 0.2366(5) 0.7106(4) 0.0478(9) Uani 0.49(2) 1 d D . P F 2
F5' F 0.1063(16) 0.3705(13) 0.6428(12) 0.133(6) Uani 0.49(2) 1 d D U P F 2
F6' F 0.0089(13) 0.166(3) 0.6800(15) 0.170(8) Uani 0.49(2) 1 d D U P F 2
F7' F 0.1648(15) 0.123(3) 0.6925(16) 0.150(7) Uani 0.49(2) 1 d D U P F 2
F8' F 0.1044(8) 0.298(2) 0.8239(11) 0.075(3) Uani 0.49(2) 1 d D U P F 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
O1 H1WA 0.92(6) . ?
O1 H1WB 0.90(8) . ?
C1 N2 1.498(5) . ?
C1 C2 1.503(6) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 N1 1.497(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 N2 1.495(4) . ?
C3 C4 1.502(6) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 N1 1.501(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 N2 1.499(4) . ?
C5 C6 1.510(6) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 N1 1.476(5) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
B1 F4 1.361(6) . ?
B1 F3 1.372(5) . ?
B1 F2 1.381(4) . ?
B1 F1 1.394(4) . ?
N2 H2 0.9800 . ?
N1 H1 0.9800 . ?
B2 F8 1.286(17) . ?
B2 F7 1.322(10) . ?
B2 F5 1.326(9) . ?
B2 F6 1.350(9) . ?
B2' F6' 1.272(10) . ?
B2' F5' 1.340(12) . ?
B2' F7' 1.346(12) . ?
B2' F8' 1.431(14) . ?

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
H1WA O1 H1WB 96(6) . . ?
N2 C1 C2 109.4(3) . . ?
N2 C1 H1A 109.8 . . ?
C2 C1 H1A 109.8 . . ?
N2 C1 H1B 109.8 . . ?
C2 C1 H1B 109.8 . . ?
H1A C1 H1B 108.2 . . ?
N1 C2 C1 108.9(3) . . ?
N1 C2 H2A 109.9 . . ?
C1 C2 H2A 109.9 . . ?
N1 C2 H2B 109.9 . . ?
C1 C2 H2B 109.9 . . ?
H2A C2 H2B 108.3 . . ?
N2 C3 C4 108.8(3) . . ?
N2 C3 H3A 109.9 . . ?
C4 C3 H3A 109.9 . . ?
N2 C3 H3B 109.9 . . ?
C4 C3 H3B 109.9 . . ?
H3A C3 H3B 108.3 . . ?
N1 C4 C3 109.4(3) . . ?
N1 C4 H4A 109.8 . . ?
C3 C4 H4A 109.8 . . ?
N1 C4 H4B 109.8 . . ?
C3 C4 H4B 109.8 . . ?
H4A C4 H4B 108.2 . . ?
N2 C5 C6 108.5(3) . . ?
N2 C5 H5A 110.0 . . ?
C6 C5 H5A 110.0 . . ?
N2 C5 H5B 110.0 . . ?
C6 C5 H5B 110.0 . . ?
H5A C5 H5B 108.4 . . ?
N1 C6 C5 109.8(3) . . ?
N1 C6 H6A 109.7 . . ?
C5 C6 H6A 109.7 . . ?
N1 C6 H6B 109.7 . . ?
C5 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
F4 B1 F3 111.1(4) . . ?
F4 B1 F2 110.5(3) . . ?
F3 B1 F2 110.6(3) . . ?
F4 B1 F1 109.2(3) . . ?
F3 B1 F1 108.1(3) . . ?
F2 B1 F1 107.2(3) . . ?
C3 N2 C1 110.0(3) . . ?
C3 N2 C5 109.4(2) . . ?
C1 N2 C5 110.0(3) . . ?
C3 N2 H2 109.1 . . ?
C1 N2 H2 109.1 . . ?
C5 N2 H2 109.1 . . ?
C6 N1 C2 109.2(3) . . ?
C6 N1 C4 110.2(3) . . ?
C2 N1 C4 110.0(3) . . ?
C6 N1 H1 109.2 . . ?
C2 N1 H1 109.2 . . ?
C4 N1 H1 109.2 . . ?
F8 B2 F7 108.4(10) . . ?
F8 B2 F5 118.0(12) . . ?
F7 B2 F5 111.6(10) . . ?
F8 B2 F6 106.3(11) . . ?
F7 B2 F6 104.6(8) . . ?
F5 B2 F6 107.0(9) . . ?
F6' B2' F5' 107.9(10) . . ?
F6' B2' F7' 106.4(12) . . ?
F5' B2' F7' 108.6(12) . . ?
F6' B2' F8' 121.4(12) . . ?
F5' B2' F8' 105.7(9) . . ?
F7' B2' F8' 106.4(8) . . ?

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
N2 C1 C2 N1 0.2(5) . . . . ?
N2 C3 C4 N1 0.5(5) . . . . ?
N2 C5 C6 N1 2.5(4) . . . . ?
C4 C3 N2 C1 -60.6(4) . . . . ?
C4 C3 N2 C5 60.4(4) . . . . ?
C2 C1 N2 C3 60.4(4) . . . . ?
C2 C1 N2 C5 -60.1(4) . . . . ?
C6 C5 N2 C3 -62.4(4) . . . . ?
C6 C5 N2 C1 58.5(4) . . . . ?
C5 C6 N1 C2 -62.5(4) . . . . ?
C5 C6 N1 C4 58.4(4) . . . . ?
C1 C2 N1 C6 60.9(4) . . . . ?
C1 C2 N1 C4 -60.1(5) . . . . ?
C3 C4 N1 C6 -60.4(4) . . . . ?
C3 C4 N1 C2 60.0(5) . . . . ?

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
N1 H1 O1 0.98 1.97 2.795(5) 140.3 1_554
N2 H2 F2 0.98 2.25 3.030(4) 135.3 .
N2 H2 F1 0.98 2.20 2.935(4) 130.5 .
O1 H1WA F3 0.92(6) 1.93(7) 2.839(5) 169(7) 4_545
N1 H1 O1 0.98 1.97 2.795(5) 140.3 1_554
N2 H2 F2 0.98 2.25 3.030(4) 135.3 .
N2 H2 F1 0.98 2.20 2.935(4) 130.5 .
O1 H1WA F3 0.92(6) 1.93(7) 2.839(5) 169(7) 4_545
N1 H1 O1 0.98 1.97 2.795(5) 140.3 1_554
N2 H2 F2 0.98 2.25 3.030(4) 135.3 .
N2 H2 F1 0.98 2.20 2.935(4) 130.5 .
O1 H1WA F3 0.92(6) 1.93(7) 2.839(5) 169(7) 4_545
N1 H1 O1 0.98 1.97 2.795(5) 140.3 1_554
N2 H2 F2 0.98 2.25 3.030(4) 135.3 .
N2 H2 F1 0.98 2.20 2.935(4) 130.5 .
O1 H1WA F3 0.92(6) 1.93(7) 2.839(5) 169(7) 4_545
N1 H1 O1 0.98 1.97 2.795(5) 140.3 1_554
N2 H2 F2 0.98 2.25 3.030(4) 135.3 .
N2 H2 F1 0.98 2.20 2.935(4) 130.5 .
O1 H1WA F3 0.92(6) 1.93(7) 2.839(5) 169(7) 4_545
N1 H1 O1 0.98 1.97 2.795(5) 140.3 1_554
N2 H2 F2 0.98 2.25 3.030(4) 135.3 .
N2 H2 F1 0.98 2.20 2.935(4) 130.5 .
O1 H1WA F3 0.92(6) 1.93(7) 2.839(5) 169(7) 4_545
N1 H1 O1 0.98 1.97 2.795(5) 140.3 1_554
N2 H2 F2 0.98 2.25 3.030(4) 135.3 .
N2 H2 F1 0.98 2.20 2.935(4) 130.5 .
O1 H1WA F3 0.92(6) 1.93(7) 2.839(5) 169(7) 4_545
N1 H1 O1 0.98 1.97 2.795(5) 140.3 1_554
N2 H2 F2 0.98 2.25 3.030(4) 135.3 .
N2 H2 F1 0.98 2.20 2.935(4) 130.5 .
O1 H1WA F3 0.92(6) 1.93(7) 2.839(5) 169(7) 4_545
N1 H1 O1 0.98 1.97 2.795(5) 140.3 1_554
N2 H2 F2 0.98 2.25 3.030(4) 135.3 .
N2 H2 F1 0.98 2.20 2.935(4) 130.5 .
O1 H1WA F3 0.92(6) 1.93(7) 2.839(5) 169(7) 4_545
O1 H1WA F3 0.92(6) 1.93(7) 2.839(5) 169(7) 4_545
N2 H2 F1 0.98 2.20 2.935(4) 130.5 .
N2 H2 F2 0.98 2.25 3.030(4) 135.3 .
N1 H1 O1 0.98 1.97 2.795(5) 140.3 1_554
O1 H1WA F3 0.92(6) 1.93(7) 2.839(5) 169(7) 4_545
N2 H2 F1 0.98 2.20 2.935(4) 130.5 .
N2 H2 F2 0.98 2.25 3.030(4) 135.3 .
N1 H1 O1 0.98 1.97 2.795(5) 140.3 1_554
O1 H1WA F3 0.92(6) 1.93(7) 2.839(5) 169(7) 4_545
N2 H2 F1 0.98 2.20 2.935(4) 130.5 .
N2 H2 F2 0.98 2.25 3.030(4) 135.3 .
N1 H1 O1 0.98 1.97 2.795(5) 140.3 1_554
O1 H1WA F3 0.92(6) 1.93(7) 2.839(5) 169(7) 4_545
N2 H2 F1 0.98 2.20 2.935(4) 130.5 .
N2 H2 F2 0.98 2.25 3.030(4) 135.3 .
N1 H1 O1 0.98 1.97 2.795(5) 140.3 1_554
O1 H1WA F3 0.92(6) 1.93(7) 2.839(5) 169(7) 4_545
N2 H2 F1 0.98 2.20 2.935(4) 130.5 .
N2 H2 F2 0.98 2.25 3.030(4) 135.3 .
N1 H1 O1 0.98 1.97 2.795(5) 140.3 1_554
O1 H1WA F3 0.92(6) 1.93(7) 2.839(5) 169(7) 4_545
N2 H2 F1 0.98 2.20 2.935(4) 130.5 .
N2 H2 F2 0.98 2.25 3.030(4) 135.3 .
N1 H1 O1 0.98 1.97 2.795(5) 140.3 1_554
O1 H1WA F3 0.92(6) 1.93(7) 2.839(5) 169(7) 4_545
N2 H2 F1 0.98 2.20 2.935(4) 130.5 .
N2 H2 F2 0.98 2.25 3.030(4) 135.3 .
N1 H1 O1 0.98 1.97 2.795(5) 140.3 1_554

_refine_diff_density_max         0.202
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.037



# start Validation Reply Form
_vrf_PLAT089_296                 
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       5.45 Note  
RESPONSE: The anomalous dispersion effects of light atoms in 
non-centrosymmetric structures are insignificant.
In this structure the F atom is the heaviest atom and 
it is unwise to attempt to use unmerged Friedel-related reflections 
simply to boost the r/p ratio.
;
####################################################################### 
# 
# 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_293
_database_code_depnum_ccdc_archive 'CCDC 1427897'
_audit_update_record             
;
2015-12-26 deposited with the CCDC.
2016-01-27 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 H14 N2, 2(Cl O4), H2 O'
_chemical_formula_sum            'C6 H16 Cl2 N2 O9'
_chemical_formula_weight         331.11

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

_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, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   13.357(10)
_cell_length_b                   8.073(7)
_cell_length_c                   11.836(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1276.3(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8696
_cell_measurement_theta_min      2.948
_cell_measurement_theta_max      27.445

_exptl_crystal_description       sheet
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.723
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.554
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.895
_exptl_absorpt_correction_T_max  0.895
_exptl_absorpt_process_details   'North et al., 1968'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8696
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.948
_diffrn_reflns_theta_max         27.445
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.774
_diffrn_reflns_point_group_measured_fraction_full 0.801
_reflns_number_total             2917
_reflns_number_gt                2087
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.503
_reflns_Friedel_fraction_max     0.546
_reflns_Friedel_fraction_full    0.591

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0528P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.021(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 645 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2917
_refine_ls_number_parameters     218
_refine_ls_number_restraints     45
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0337
_refine_ls_wR_factor_ref         0.0841
_refine_ls_wR_factor_gt          0.0818
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1425(3) 0.4483(5) 0.2890(3) 0.0480(9) Uani 1 1 d . . . A 4
H1A H 0.2149 0.4570 0.2871 0.058 Uiso 1 1 calc R U . A 4
H1B H 0.1148 0.5593 0.2882 0.058 Uiso 1 1 calc R U . A 4
C2 C 0.1061(3) 0.3531(5) 0.1871(3) 0.0566(11) Uani 1 1 d . . . A 4
H2A H 0.0628 0.4228 0.1416 0.068 Uiso 1 1 calc R U . A 4
H2B H 0.1626 0.3195 0.1411 0.068 Uiso 1 1 calc R U . A 4
C3 C 0.1561(3) 0.1900(4) 0.3961(4) 0.0453(9) Uani 1 1 d . . . A 4
H3A H 0.1377 0.1330 0.4652 0.054 Uiso 1 1 calc R U . A 4
H3B H 0.2285 0.1977 0.3929 0.054 Uiso 1 1 calc R U . A 4
C4 C 0.1171(4) 0.0960(5) 0.2946(4) 0.0597(11) Uani 1 1 d . . . A 4
H4A H 0.1729 0.0598 0.2483 0.072 Uiso 1 1 calc R U . A 4
H4B H 0.0809 -0.0014 0.3197 0.072 Uiso 1 1 calc R U . A 4
C5 C -0.0002(3) 0.3487(4) 0.3997(4) 0.0443(8) Uani 1 1 d . . . A 4
H5A H -0.0291 0.4589 0.4025 0.053 Uiso 1 1 calc R U . A 4
H5B H -0.0201 0.2896 0.4674 0.053 Uiso 1 1 calc R U . A 4
C6 C -0.0379(3) 0.2578(6) 0.2958(4) 0.0549(10) Uani 1 1 d . . . A 4
H6A H -0.0771 0.1622 0.3185 0.066 Uiso 1 1 calc R U . A 4
H6B H -0.0805 0.3303 0.2515 0.066 Uiso 1 1 calc R U . A 4
Cl1 Cl 0.22699(6) 0.72133(9) 0.52888(7) 0.0384(2) Uani 1 1 d . . . B 4
H1WA H 0.121(4) 0.012(7) 0.014(6) 0.091(19) Uiso 1 1 d . . . C 4
H1WB H 0.062(5) 0.119(11) -0.028(8) 0.14(4) Uiso 1 1 d . . . D 4
N1 N 0.1106(2) 0.3603(3) 0.3942(3) 0.0363(6) Uani 1 1 d . . . A 4
H1 H 0.1346 0.4225 0.4599 0.044 Uiso 1 1 calc R U . A 4
N2 N 0.0496(3) 0.2033(4) 0.2265(3) 0.0438(7) Uani 1 1 d . . . A 4
H2 H 0.0256 0.1412 0.1607 0.053 Uiso 1 1 calc R U . A 4
O1 O 0.0658(3) 0.0563(4) 0.0152(3) 0.0688(9) Uani 1 1 d . . . E 4
O2 O 0.27479(19) 0.5726(3) 0.4909(3) 0.0614(9) Uani 1 1 d . . . B 4
O3 O 0.1213(2) 0.7004(4) 0.5168(3) 0.0644(8) Uani 1 1 d . . . B 4
O4 O 0.2606(3) 0.8556(4) 0.4612(4) 0.0764(10) Uani 1 1 d . . . B 4
O5 O 0.2507(3) 0.7508(4) 0.6444(3) 0.0688(9) Uani 1 1 d . . . B 4
Cl2 Cl 0.08844(6) 0.23972(9) 0.71355(8) 0.0388(2) Uani 0.60(4) 1 d D . P F 1
O6 O 0.1457(15) 0.345(2) 0.6489(13) 0.093(5) Uani 0.60(4) 1 d D . P F 1
O7 O -0.0155(8) 0.250(2) 0.6776(13) 0.087(4) Uani 0.60(4) 1 d D . P F 1
O8 O 0.1197(12) 0.0757(10) 0.7000(14) 0.082(3) Uani 0.60(4) 1 d D . P F 1
O9 O 0.0914(14) 0.279(2) 0.8294(9) 0.090(5) Uani 0.60(4) 1 d D . P F 1
Cl2' Cl 0.08844(6) 0.23972(9) 0.71355(8) 0.0388(2) Uani 0.40(4) 1 d D . P F 2
O6' O 0.119(2) 0.379(2) 0.6412(17) 0.071(5) Uani 0.40(4) 1 d D U P F 2
O7' O -0.0082(13) 0.201(4) 0.692(2) 0.097(7) Uani 0.40(4) 1 d D U P F 2
O8' O 0.159(2) 0.111(3) 0.695(2) 0.103(8) Uani 0.40(4) 1 d D U P F 2
O9' O 0.1040(14) 0.303(3) 0.8275(12) 0.057(5) Uani 0.40(4) 1 d D U P F 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
C1 N1 1.495(5) . ?
C1 C2 1.510(6) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 N2 1.500(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 N1 1.504(4) . ?
C3 C4 1.513(6) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 N2 1.488(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 N1 1.484(4) . ?
C5 C6 1.518(6) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 N2 1.494(6) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
Cl1 O4 1.421(3) . ?
Cl1 O5 1.423(4) . ?
Cl1 O3 1.429(3) . ?
Cl1 O2 1.432(3) . ?
N1 H1 0.9800 . ?
N2 H2 0.9800 . ?
O1 H1WA 0.82(6) . ?
O1 H1WB 0.72(9) . ?
Cl2 O6 1.377(10) . ?
Cl2 O8 1.398(7) . ?
Cl2 O9 1.409(11) . ?
Cl2 O7 1.454(10) . ?
Cl2' O7' 1.353(13) . ?
Cl2' O8' 1.412(13) . ?
Cl2' O9' 1.456(13) . ?
Cl2' O6' 1.467(14) . ?

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
N1 C1 C2 109.3(3) . . ?
N1 C1 H1A 109.8 . . ?
C2 C1 H1A 109.8 . . ?
N1 C1 H1B 109.8 . . ?
C2 C1 H1B 109.8 . . ?
H1A C1 H1B 108.3 . . ?
N2 C2 C1 108.9(3) . . ?
N2 C2 H2A 109.9 . . ?
C1 C2 H2A 109.9 . . ?
N2 C2 H2B 109.9 . . ?
C1 C2 H2B 109.9 . . ?
H2A C2 H2B 108.3 . . ?
N1 C3 C4 107.9(3) . . ?
N1 C3 H3A 110.1 . . ?
C4 C3 H3A 110.1 . . ?
N1 C3 H3B 110.1 . . ?
C4 C3 H3B 110.1 . . ?
H3A C3 H3B 108.4 . . ?
N2 C4 C3 110.3(3) . . ?
N2 C4 H4A 109.6 . . ?
C3 C4 H4A 109.6 . . ?
N2 C4 H4B 109.6 . . ?
C3 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?
N1 C5 C6 109.0(3) . . ?
N1 C5 H5A 109.9 . . ?
C6 C5 H5A 109.9 . . ?
N1 C5 H5B 109.9 . . ?
C6 C5 H5B 109.9 . . ?
H5A C5 H5B 108.3 . . ?
N2 C6 C5 109.1(3) . . ?
N2 C6 H6A 109.9 . . ?
C5 C6 H6A 109.9 . . ?
N2 C6 H6B 109.9 . . ?
C5 C6 H6B 109.9 . . ?
H6A C6 H6B 108.3 . . ?
O4 Cl1 O5 110.1(2) . . ?
O4 Cl1 O3 110.3(2) . . ?
O5 Cl1 O3 109.6(2) . . ?
O4 Cl1 O2 108.8(2) . . ?
O5 Cl1 O2 110.0(2) . . ?
O3 Cl1 O2 108.06(18) . . ?
C5 N1 C1 110.5(3) . . ?
C5 N1 C3 110.2(3) . . ?
C1 N1 C3 109.4(3) . . ?
C5 N1 H1 108.9 . . ?
C1 N1 H1 108.9 . . ?
C3 N1 H1 108.9 . . ?
C4 N2 C6 110.4(4) . . ?
C4 N2 C2 109.4(3) . . ?
C6 N2 C2 109.1(3) . . ?
C4 N2 H2 109.3 . . ?
C6 N2 H2 109.3 . . ?
C2 N2 H2 109.3 . . ?
H1WA O1 H1WB 111(7) . . ?
O6 Cl2 O8 110.9(9) . . ?
O6 Cl2 O9 112.7(10) . . ?
O8 Cl2 O9 108.5(9) . . ?
O6 Cl2 O7 109.4(8) . . ?
O8 Cl2 O7 107.7(7) . . ?
O9 Cl2 O7 107.4(8) . . ?
O7' Cl2' O8' 115.9(12) . . ?
O7' Cl2' O9' 113.2(12) . . ?
O8' Cl2' O9' 107.5(11) . . ?
O7' Cl2' O6' 109.0(11) . . ?
O8' Cl2' O6' 106.8(13) . . ?
O9' Cl2' O6' 103.6(11) . . ?

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 C1 C2 N2 0.4(5) . . . . ?
N1 C3 C4 N2 1.3(5) . . . . ?
N1 C5 C6 N2 2.9(4) . . . . ?
C6 C5 N1 C1 58.4(4) . . . . ?
C6 C5 N1 C3 -62.6(4) . . . . ?
C2 C1 N1 C5 -60.6(4) . . . . ?
C2 C1 N1 C3 60.9(4) . . . . ?
C4 C3 N1 C5 60.1(4) . . . . ?
C4 C3 N1 C1 -61.6(4) . . . . ?
C3 C4 N2 C6 -60.4(5) . . . . ?
C3 C4 N2 C2 59.7(5) . . . . ?
C5 C6 N2 C4 57.8(4) . . . . ?
C5 C6 N2 C2 -62.5(4) . . . . ?
C1 C2 N2 C4 -60.5(5) . . . . ?
C1 C2 N2 C6 60.4(4) . . . . ?

_refine_diff_density_max         0.232
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.042

####################################################################### 
# 
# 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_233
_database_code_depnum_ccdc_archive 'CCDC 1427898'
_audit_update_record             
;
2015-12-26 deposited with the CCDC.
2016-01-27 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 H14 N2, 2(Cl O4), H2 O'
_chemical_formula_sum            'C6 H16 Cl2 N2 O9'
_chemical_formula_weight         331.11

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

_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, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'

_cell_length_a                   13.296(10)
_cell_length_b                   8.069(6)
_cell_length_c                   11.772(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1263.0(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8501
_cell_measurement_theta_min      3.461
_cell_measurement_theta_max      27.450

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.741
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.560
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8501
_diffrn_reflns_av_unetI/netI     0.0465
_diffrn_reflns_av_R_equivalents  0.0712
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.461
_diffrn_reflns_theta_max         27.450
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.771
_diffrn_reflns_point_group_measured_fraction_full 0.797
_reflns_number_total             2879
_reflns_number_gt                2163
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.503
_reflns_Friedel_fraction_max     0.544
_reflns_Friedel_fraction_full    0.587

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0232P)²+2.9545P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.010(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 636 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.15(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2222
_refine_ls_number_parameters     179
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0553
_refine_ls_wR_factor_ref         0.1270
_refine_ls_wR_factor_gt          0.1263
_refine_ls_goodness_of_fit_ref   1.173
_refine_ls_restrained_S_all      1.172
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6051(7) 0.8537(10) 0.6857(6) 0.043(2) Uani 1 1 d . . . . .
H1A H 0.6618 0.8217 0.7327 0.052 Uiso 1 1 calc R U . . .
H1B H 0.5606 0.9225 0.7307 0.052 Uiso 1 1 calc R U . . .
C2 C 0.6418(6) 0.9495(8) 0.5829(6) 0.0384(16) Uani 1 1 d . . . . .
H2A H 0.6133 1.0601 0.5832 0.046 Uiso 1 1 calc R U . . .
H2B H 0.7145 0.9595 0.5853 0.046 Uiso 1 1 calc R U . . .
C3 C 0.6178(8) 0.5959(10) 0.5773(8) 0.060(3) Uani 1 1 d . . . . .
H3A H 0.5815 0.4978 0.5530 0.072 Uiso 1 1 calc R U . . .
H3B H 0.6741 0.5606 0.6236 0.072 Uiso 1 1 calc R U . . .
C4 C 0.6559(5) 0.6870(8) 0.4756(7) 0.0353(15) Uani 1 1 d . . . . .
H4A H 0.6362 0.6296 0.4066 0.042 Uiso 1 1 calc R U . . .
H4B H 0.7287 0.6934 0.4777 0.042 Uiso 1 1 calc R U . . .
C5 C 0.4641(6) 0.7573(11) 0.5758(7) 0.048(2) Uani 1 1 d . . . . .
H5A H 0.4215 0.8299 0.6205 0.058 Uiso 1 1 calc R U . . .
H5B H 0.4246 0.6616 0.5535 0.058 Uiso 1 1 calc R U . . .
C6 C 0.4994(5) 0.8467(9) 0.4723(7) 0.0372(15) Uani 1 1 d . . . . .
H6A H 0.4793 0.7865 0.4047 0.045 Uiso 1 1 calc R U . . .
H6B H 0.4696 0.9564 0.4694 0.045 Uiso 1 1 calc R U . . .
Cl1 Cl 0.77285(11) 0.22100(17) 0.84186(13) 0.0293(4) Uani 1 1 d . . . . .
Cl2 Cl 0.91119(11) 0.74147(17) 0.65756(15) 0.0289(4) Uani 1 1 d . . . . .
H1WA H 0.608(4) 0.483(7) 0.875(6) 0.043 Uiso 1 1 d D U . . .
H1WB H 0.561(6) 0.627(7) 0.908(5) 0.043 Uiso 1 1 d D U . . .
N1 N 0.6108(4) 0.8599(6) 0.4774(5) 0.0267(11) Uani 1 1 d . . . . .
H1 H 0.6319 0.9179 0.4155 0.032 Uiso 1 1 d R U . . .
N2 N 0.5504(5) 0.7028(7) 0.6454(5) 0.0370(14) Uani 1 1 d . . . . .
H2 H 0.5287 0.6445 0.7069 0.044 Uiso 1 1 d R U . . .
O3 O 0.8795(4) 0.1998(7) 0.8548(6) 0.0491(13) Uani 1 1 d . . . . .
O4 O 0.7393(5) 0.3586(6) 0.9103(6) 0.0613(17) Uani 1 1 d . . . . .
O5 O 0.7483(5) 0.2497(7) 0.7256(6) 0.0519(15) Uani 1 1 d . . . . .
O2 O 0.7235(4) 0.0729(6) 0.8812(5) 0.0458(14) Uani 1 1 d . . . . .
O6 O 0.8654(7) 0.8631(9) 0.7242(6) 0.083(3) Uani 1 1 d . . . . .
O9 O 0.9042(5) 0.7884(7) 0.5425(5) 0.0516(15) Uani 1 1 d . . . . .
O7 O 0.8694(7) 0.5840(8) 0.6713(7) 0.090(3) Uani 1 1 d . . . . .
O8 O 1.0144(6) 0.7333(11) 0.6902(7) 0.085(3) Uani 1 1 d . . . . .
O1 O 0.5648(5) 0.5547(6) 0.8570(5) 0.0549(15) Uani 1 1 d 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 N2 1.496(8) . ?
C1 C2 1.516(10) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 N1 1.495(8) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 N2 1.480(10) . ?
C3 C4 1.493(10) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 N1 1.519(8) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 N2 1.476(10) . ?
C5 C6 1.491(11) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 N1 1.486(8) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
Cl1 O5 1.427(7) . ?
Cl1 O3 1.436(5) . ?
Cl1 O2 1.440(5) . ?
Cl1 O4 1.443(6) . ?
Cl2 O7 1.396(6) . ?
Cl2 O6 1.396(6) . ?
Cl2 O9 1.409(6) . ?
Cl2 O8 1.427(8) . ?
N1 H1 0.9100 . ?
N2 H2 0.9101 . ?
O1 H1WA 0.85(2) . ?
O1 H1WB 0.84(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 C1 C2 108.6(5) . . ?
N2 C1 H1A 110.0 . . ?
C2 C1 H1A 110.0 . . ?
N2 C1 H1B 110.0 . . ?
C2 C1 H1B 110.0 . . ?
H1A C1 H1B 108.4 . . ?
N1 C2 C1 109.1(5) . . ?
N1 C2 H2A 109.9 . . ?
C1 C2 H2A 109.9 . . ?
N1 C2 H2B 109.9 . . ?
C1 C2 H2B 109.9 . . ?
H2A C2 H2B 108.3 . . ?
N2 C3 C4 110.7(6) . . ?
N2 C3 H3A 109.5 . . ?
C4 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
C3 C4 N1 107.9(6) . . ?
C3 C4 H4A 110.1 . . ?
N1 C4 H4A 110.1 . . ?
C3 C4 H4B 110.1 . . ?
N1 C4 H4B 110.1 . . ?
H4A C4 H4B 108.4 . . ?
N2 C5 C6 110.7(6) . . ?
N2 C5 H5A 109.5 . . ?
C6 C5 H5A 109.5 . . ?
N2 C5 H5B 109.5 . . ?
C6 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
N1 C6 C5 108.3(6) . . ?
N1 C6 H6A 110.0 . . ?
C5 C6 H6A 110.0 . . ?
N1 C6 H6B 110.0 . . ?
C5 C6 H6B 110.0 . . ?
H6A C6 H6B 108.4 . . ?
O5 Cl1 O3 110.3(4) . . ?
O5 Cl1 O2 109.8(3) . . ?
O3 Cl1 O2 108.4(3) . . ?
O5 Cl1 O4 109.9(4) . . ?
O3 Cl1 O4 109.7(4) . . ?
O2 Cl1 O4 108.6(4) . . ?
O7 Cl2 O6 113.7(6) . . ?
O7 Cl2 O9 109.2(4) . . ?
O6 Cl2 O9 108.8(4) . . ?
O7 Cl2 O8 108.0(6) . . ?
O6 Cl2 O8 107.5(5) . . ?
O9 Cl2 O8 109.5(4) . . ?
C6 N1 C2 110.1(5) . . ?
C6 N1 C4 109.1(5) . . ?
C2 N1 C4 110.3(5) . . ?
C6 N1 H1 108.2 . . ?
C2 N1 H1 109.3 . . ?
C4 N1 H1 109.8 . . ?
C5 N2 C3 110.1(7) . . ?
C5 N2 C1 108.1(6) . . ?
C3 N2 C1 110.6(7) . . ?
C5 N2 H2 110.4 . . ?
C3 N2 H2 108.8 . . ?
C1 N2 H2 108.8 . . ?
H1WA O1 H1WB 110(4) . . ?

_refine_diff_density_max         0.352
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.080


# start Validation Reply Form
_vrf_PLAT340_233                 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01133 Ang.  
RESPONSE: The crystal quality degrades when the temperature decreases and 
one perchlorate still has a little disorder. We have tried to collect 
several low-temperature data sets,but they show the same problem 
like the isomorphic crystal [(H2dabco)(H2O)](BF4)2. Although the C-C 
presision can be improved by damp restrain, small molecular structure 
can't be refined by it.
;
# end Validation Reply Form

#END CIF
