# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_HighB_100K
_audit_block_doi                 10.5517/ccdc.csd.cc1zq3zs
_database_code_depnum_ccdc_archive 'CCDC 1838516'
_audit_update_record             
;
2018-04-20 deposited with the CCDC.
2018-06-15 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C14 H16 Cl2 N2 O6'
_chemical_formula_moiety         'C14 H16 Cl2 N2 O6'
_chemical_formula_weight         379.20
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   4.9143(16)
_cell_length_b                   7.458(2)
_cell_length_c                   11.698(4)
_cell_angle_alpha                73.270(5)
_cell_angle_beta                 89.528(6)
_cell_angle_gamma                69.737(5)
_cell_volume                     383.2(2)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2502
_cell_measurement_theta_min      1.80
_cell_measurement_theta_max      27.40
_cell_measurement_temperature    100
#------------------------------------------------------------------------------
_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.014
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.643
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             196.00
_exptl_absorpt_coefficient_mu    0.440
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.544
_exptl_absorpt_correction_T_max  1.000

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      100
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.703010
_diffrn_measurement_device_type  'Rigaku R-AXIS IV'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 14.706
_diffrn_reflns_number            4220
_diffrn_reflns_av_R_equivalents  0.0613
_diffrn_reflns_theta_max         25.045
_diffrn_reflns_theta_min         1.807
_diffrn_reflns_theta_full        24.948
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             1393
_reflns_number_gt                1155
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0434
_refine_ls_wR_factor_ref         0.1120
_refine_ls_wR_factor_gt          0.1071
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_number_reflns         1393
_refine_ls_number_parameters     141
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0635P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.38
_refine_diff_density_min         -0.38
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Cl Cl 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.17920(14) 0.23288(9) 0.94281(5) 0.0215(2) Uani 1 1 d . . . . .
O1 O 0.4366(4) 0.2073(3) 1.17539(16) 0.0263(5) Uani 1 1 d . . . . .
O2 O 0.2910(4) 0.5694(3) 0.76907(15) 0.0215(5) Uani 1 1 d . . . . .
O3 O 0.3792(4) 0.8250(3) 0.58782(15) 0.0216(5) Uani 1 1 d . . . . .
N1 N 0.3232(5) 0.9143(3) 0.38415(19) 0.0179(5) Uani 1 1 d . . . . .
C1 C 0.4615(5) 0.3404(4) 1.0927(2) 0.0178(6) Uani 1 1 d . . . . .
C2 C 0.3536(6) 0.3820(4) 0.9698(2) 0.0179(6) Uani 1 1 d . . . . .
C3 C 0.3873(5) 0.5300(4) 0.8808(2) 0.0175(6) Uani 1 1 d . . . . .
C4 C 0.2868(6) 0.8138(4) 0.4924(2) 0.0171(6) Uani 1 1 d . . . . .
C5 C 0.1174(6) 0.6865(4) 0.4823(2) 0.0189(6) Uani 1 1 d . . . . .
C6 C 0.0932(7) 0.7053(4) 0.3494(2) 0.0229(6) Uani 1 1 d . . . . .
C7 C 0.1818(6) 0.8831(4) 0.2869(2) 0.0219(6) Uani 1 1 d . . . . .
H1 H 0.397(6) 1.000(4) 0.373(2) 0.014(7) Uiso 1 1 d . . . . .
H2 H 0.318(7) 0.671(5) 0.719(3) 0.036(9) Uiso 1 1 d . . . . .
H3 H 0.208(6) 0.546(4) 0.537(3) 0.021(7) Uiso 1 1 d . . . . .
H4 H -0.069(7) 0.740(4) 0.513(2) 0.026(8) Uiso 1 1 d . . . . .
H5 H -0.108(7) 0.732(5) 0.315(3) 0.039(9) Uiso 1 1 d . . . . .
H6 H 0.224(6) 0.589(4) 0.339(2) 0.018(7) Uiso 1 1 d . . . . .
H7 H 0.313(6) 0.854(4) 0.222(2) 0.022(7) Uiso 1 1 d . . . . .
H8 H 0.006(6) 1.001(4) 0.251(2) 0.024(7) Uiso 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.5 (Rigaku, 2017)'
_computing_molecular_graphics    'CrystalStructure 4.2.5'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C2 1.714(3) . ?
O1 C1 1.211(3) . ?
O2 C3 1.309(3) . ?
O2 H2 0.87(3) . ?
O3 C4 1.244(3) . ?
N1 C4 1.319(3) . ?
N1 C7 1.452(3) . ?
N1 H1 0.82(3) . ?
C1 C2 1.444(4) . ?
C1 C3 1.502(4) 2_667 ?
C2 C3 1.338(4) . ?
C3 C1 1.502(4) 2_667 ?
C4 C5 1.490(4) . ?
C5 C6 1.523(4) . ?
C5 H3 1.00(3) . ?
C5 H4 0.97(3) . ?
C6 C7 1.523(4) . ?
C6 H5 1.00(3) . ?
C6 H6 0.93(3) . ?
C7 H7 1.02(3) . ?
C7 H8 0.98(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
C3 O2 H2 115(2) . . ?
C4 N1 C7 114.4(2) . . ?
C4 N1 H1 122.0(18) . . ?
C7 N1 H1 122.9(18) . . ?
O1 C1 C2 123.7(2) . . ?
O1 C1 C3 118.3(2) . 2_667 ?
C2 C1 C3 118.0(2) . 2_667 ?
C3 C2 C1 121.8(2) . . ?
C3 C2 Cl1 121.3(2) . . ?
C1 C2 Cl1 116.9(2) . . ?
O2 C3 C2 122.5(2) . . ?
O2 C3 C1 117.3(2) . 2_667 ?
C2 C3 C1 120.2(2) . 2_667 ?
O3 C4 N1 124.9(2) . . ?
O3 C4 C5 125.6(2) . . ?
N1 C4 C5 109.5(2) . . ?
C4 C5 C6 104.8(2) . . ?
C4 C5 H3 112.2(16) . . ?
C6 C5 H3 114.7(15) . . ?
C4 C5 H4 106.8(17) . . ?
C6 C5 H4 113.9(16) . . ?
H3 C5 H4 104(2) . . ?
C5 C6 C7 105.2(2) . . ?
C5 C6 H5 114.3(18) . . ?
C7 C6 H5 108.4(19) . . ?
C5 C6 H6 108.2(17) . . ?
C7 C6 H6 110.2(17) . . ?
H5 C6 H6 110(2) . . ?
N1 C7 C6 103.6(2) . . ?
N1 C7 H7 113.6(16) . . ?
C6 C7 H7 111.2(15) . . ?
N1 C7 H8 109.6(16) . . ?
C6 C7 H8 109.3(17) . . ?
H7 C7 H8 109(2) . . ?

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
O1 C1 C2 C3 -179.6(3) . . . . ?
C3 C1 C2 C3 0.5(4) 2_667 . . . ?
O1 C1 C2 Cl1 0.5(4) . . . . ?
C3 C1 C2 Cl1 -179.42(18) 2_667 . . . ?
C1 C2 C3 O2 179.9(2) . . . . ?
Cl1 C2 C3 O2 -0.1(4) . . . . ?
C1 C2 C3 C1 -0.5(4) . . . 2_667 ?
Cl1 C2 C3 C1 179.40(18) . . . 2_667 ?
C7 N1 C4 O3 -177.0(3) . . . . ?
C7 N1 C4 C5 2.7(3) . . . . ?
O3 C4 C5 C6 -172.7(3) . . . . ?
N1 C4 C5 C6 7.6(3) . . . . ?
C4 C5 C6 C7 -14.1(3) . . . . ?
C4 N1 C7 C6 -11.7(3) . . . . ?
C5 C6 C7 N1 15.3(3) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

_shelxl_version_number           2014-3


####################################################################### 
# 
# 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_HighB
_audit_block_doi                 10.5517/ccdc.csd.cc1zq41w
_database_code_depnum_ccdc_archive 'CCDC 1838518'
_audit_update_record             
;
2018-04-20 deposited with the CCDC.
2018-06-15 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C14 H16 Cl2 N2 O6'
_chemical_formula_moiety         'C14 H16 Cl2 N2 O6'
_chemical_formula_weight         379.20
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   4.987(3)
_cell_length_b                   7.592(4)
_cell_length_c                   11.718(6)
_cell_angle_alpha                72.926(6)
_cell_angle_beta                 89.449(6)
_cell_angle_gamma                71.157(6)
_cell_volume                     399.6(4)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1685
_cell_measurement_theta_min      1.80
_cell_measurement_theta_max      27.38
_cell_measurement_temperature    298
#------------------------------------------------------------------------------
_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.576
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             196.00
_exptl_absorpt_coefficient_mu    0.422
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.552
_exptl_absorpt_correction_T_max  1.000

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      298
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.703010
_diffrn_measurement_device_type  'Rigaku R-AXIS IV'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 14.706
_diffrn_reflns_number            5228
_diffrn_reflns_av_R_equivalents  0.0658
_diffrn_reflns_theta_max         27.160
_diffrn_reflns_theta_min         1.806
_diffrn_reflns_theta_full        24.948
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             1821
_reflns_number_gt                1000
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1135
_refine_ls_R_factor_gt           0.0520
_refine_ls_wR_factor_ref         0.1302
_refine_ls_wR_factor_gt          0.1077
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_number_reflns         1821
_refine_ls_number_parameters     141
_refine_ls_goodness_of_fit_ref   0.944
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0595P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.31
_refine_diff_density_min         -0.23
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Cl Cl 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.81739(19) 0.76494(12) 0.05574(7) 0.0574(3) Uani 1 1 d . . . . .
O1 O 0.5591(6) 0.7907(3) -0.17451(19) 0.0715(8) Uani 1 1 d . . . . .
O2 O 0.7055(5) 0.4322(4) 0.22970(19) 0.0566(7) Uani 1 1 d . . . . .
O3 O 0.6210(5) 0.1769(3) 0.41253(18) 0.0557(7) Uani 1 1 d . . . . .
N1 N 0.6803(6) 0.0836(4) 0.6155(2) 0.0471(7) Uani 1 1 d . . . . .
C1 C 0.5370(7) 0.6583(5) -0.0920(3) 0.0458(8) Uani 1 1 d . . . . .
C2 C 0.6454(6) 0.6175(4) 0.0301(3) 0.0422(8) Uani 1 1 d . . . . .
C3 C 0.6108(7) 0.4708(4) 0.1180(3) 0.0421(7) Uani 1 1 d . . . . .
C4 C 0.7141(7) 0.1854(4) 0.5075(3) 0.0397(7) Uani 1 1 d . . . . .
C5 C 0.8778(9) 0.3120(6) 0.5180(3) 0.0486(9) Uani 1 1 d . . . . .
C6 C 0.9089(10) 0.2862(7) 0.6509(3) 0.0616(11) Uani 1 1 d . . . . .
C7 C 0.8135(10) 0.1164(6) 0.7118(3) 0.0561(10) Uani 1 1 d . . . . .
H1 H 0.619(6) -0.009(4) 0.625(2) 0.037(8) Uiso 1 1 d . . . . .
H2 H 0.681(9) 0.331(6) 0.283(4) 0.097(15) Uiso 1 1 d . . . . .
H3 H 1.050(7) 0.268(4) 0.489(3) 0.052(10) Uiso 1 1 d . . . . .
H4 H 0.809(7) 0.447(5) 0.469(3) 0.054(9) Uiso 1 1 d . . . . .
H5 H 0.823(10) 0.397(6) 0.673(4) 0.104(16) Uiso 1 1 d . . . . .
H6 H 1.109(10) 0.253(6) 0.682(4) 0.112(16) Uiso 1 1 d . . . . .
H7 H 0.990(9) 0.005(5) 0.745(3) 0.081(13) Uiso 1 1 d . . . . .
H8 H 0.681(8) 0.148(5) 0.772(3) 0.077(12) Uiso 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.5 (Rigaku, 2017)'
_computing_molecular_graphics    'CrystalStructure 4.2.5'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C2 1.704(3) . ?
O1 C1 1.207(3) . ?
O2 C3 1.311(3) . ?
O2 H2 0.88(4) . ?
O3 C4 1.237(3) . ?
N1 C4 1.317(4) . ?
N1 C7 1.437(4) . ?
N1 H1 0.83(3) . ?
C1 C2 1.444(4) . ?
C1 C3 1.498(4) 2_665 ?
C2 C3 1.333(4) . ?
C3 C1 1.498(4) 2_665 ?
C4 C5 1.478(4) . ?
C5 C6 1.514(5) . ?
C5 H3 0.92(3) . ?
C5 H4 0.96(3) . ?
C6 C7 1.499(5) . ?
C6 H5 0.93(4) . ?
C6 H6 0.99(5) . ?
C7 H7 0.99(4) . ?
C7 H8 0.99(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O2 H2 117(3) . . ?
C4 N1 C7 114.6(3) . . ?
C4 N1 H1 121.0(19) . . ?
C7 N1 H1 123.1(19) . . ?
O1 C1 C2 123.6(3) . . ?
O1 C1 C3 118.1(3) . 2_665 ?
C2 C1 C3 118.3(3) . 2_665 ?
C3 C2 C1 121.0(3) . . ?
C3 C2 Cl1 122.1(2) . . ?
C1 C2 Cl1 116.9(2) . . ?
O2 C3 C2 122.0(3) . . ?
O2 C3 C1 117.3(3) . 2_665 ?
C2 C3 C1 120.7(3) . 2_665 ?
O3 C4 N1 125.1(3) . . ?
O3 C4 C5 125.7(3) . . ?
N1 C4 C5 109.3(3) . . ?
C4 C5 C6 104.8(3) . . ?
C4 C5 H3 107.1(19) . . ?
C6 C5 H3 112.3(19) . . ?
C4 C5 H4 117.7(19) . . ?
C6 C5 H4 113.8(18) . . ?
H3 C5 H4 101(3) . . ?
C7 C6 C5 105.8(3) . . ?
C7 C6 H5 115(3) . . ?
C5 C6 H5 116(3) . . ?
C7 C6 H6 108(3) . . ?
C5 C6 H6 112(3) . . ?
H5 C6 H6 100(4) . . ?
N1 C7 C6 104.0(3) . . ?
N1 C7 H7 109(2) . . ?
C6 C7 H7 105(2) . . ?
N1 C7 H8 113(2) . . ?
C6 C7 H8 110(2) . . ?
H7 C7 H8 115(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 178.9(3) . . . . ?
C3 C1 C2 C3 -1.2(5) 2_665 . . . ?
O1 C1 C2 Cl1 -1.0(5) . . . . ?
C3 C1 C2 Cl1 178.9(2) 2_665 . . . ?
C1 C2 C3 O2 -179.5(3) . . . . ?
Cl1 C2 C3 O2 0.4(5) . . . . ?
C1 C2 C3 C1 1.2(6) . . . 2_665 ?
Cl1 C2 C3 C1 -178.9(2) . . . 2_665 ?
C7 N1 C4 O3 178.8(4) . . . . ?
C7 N1 C4 C5 -1.7(4) . . . . ?
O3 C4 C5 C6 173.3(4) . . . . ?
N1 C4 C5 C6 -6.2(4) . . . . ?
C4 C5 C6 C7 11.2(5) . . . . ?
C4 N1 C7 C6 8.9(5) . . . . ?
C5 C6 C7 N1 -11.9(5) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

_shelxl_version_number           2014-3


####################################################################### 
# 
# 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_LowB
_audit_block_doi                 10.5517/ccdc.csd.cc1zq42x
_database_code_depnum_ccdc_archive 'CCDC 1838519'
_audit_update_record             
;
2018-04-20 deposited with the CCDC.
2018-06-15 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C14 H16 Cl2 N2 O6'
_chemical_formula_moiety         'C14 H16 Cl2 N2 O6'
_chemical_formula_weight         379.20
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   4.6904(17)
_cell_length_b                   8.921(3)
_cell_length_c                   9.833(3)
_cell_angle_alpha                103.357(7)
_cell_angle_beta                 96.447(7)
_cell_angle_gamma                93.984(7)
_cell_volume                     395.8(2)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2561
_cell_measurement_theta_min      2.13
_cell_measurement_theta_max      27.20
_cell_measurement_temperature    100
#------------------------------------------------------------------------------
_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.591
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             196.00
_exptl_absorpt_coefficient_mu    0.426
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.464
_exptl_absorpt_correction_T_max  1.000

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      100
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.703010
_diffrn_measurement_device_type  'Rigaku R-AXIS IV'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 14.706
_diffrn_reflns_number            5200
_diffrn_reflns_av_R_equivalents  0.0830
_diffrn_reflns_theta_max         27.154
_diffrn_reflns_theta_min         2.124
_diffrn_reflns_theta_full        24.948
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             1799
_reflns_number_gt                1422
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0535
_refine_ls_wR_factor_ref         0.1428
_refine_ls_wR_factor_gt          0.1334
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_number_reflns         1799
_refine_ls_number_parameters     141
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0806P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.60
_refine_diff_density_min         -0.60
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Cl Cl 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.40381(13) 0.24243(6) 0.04031(6) 0.0215(2) Uani 1 1 d . . . . .
O1 O -0.0426(4) 0.2384(2) -0.19558(18) 0.0222(4) Uani 1 1 d . . . . .
O2 O 0.4107(4) 0.5526(2) 0.23311(19) 0.0210(4) Uani 1 1 d . . . . .
O3 O 0.5004(4) 0.8080(2) 0.41721(19) 0.0214(4) Uani 1 1 d . . . . .
N1 N 0.8116(4) 0.9269(2) 0.6129(2) 0.0178(5) Uani 1 1 d . . . . .
C1 C -0.0206(5) 0.3555(3) -0.1034(2) 0.0163(5) Uani 1 1 d . . . . .
C2 C 0.1882(5) 0.3869(3) 0.0226(3) 0.0161(5) Uani 1 1 d . . . . .
C3 C 0.2171(5) 0.5217(3) 0.1199(3) 0.0173(5) Uani 1 1 d . . . . .
C4 C 0.7074(5) 0.8081(3) 0.5074(3) 0.0172(5) Uani 1 1 d . . . . .
C5 C 0.8825(6) 0.6748(3) 0.5140(3) 0.0195(5) Uani 1 1 d . . . . .
C6 C 1.0674(6) 0.7237(3) 0.6568(3) 0.0207(6) Uani 1 1 d . . . . .
C7 C 1.0637(6) 0.8996(3) 0.7006(3) 0.0215(6) Uani 1 1 d . . . . .
H1 H 0.767(6) 1.005(4) 0.624(3) 0.023(8) Uiso 1 1 d . . . . .
H2 H 0.426(8) 0.652(5) 0.290(4) 0.064(12) Uiso 1 1 d . . . . .
H3 H 0.755(6) 0.568(3) 0.495(3) 0.020(7) Uiso 1 1 d . . . . .
H4 H 0.987(6) 0.659(3) 0.437(3) 0.029(8) Uiso 1 1 d . . . . .
H5 H 1.274(6) 0.696(3) 0.656(3) 0.023(7) Uiso 1 1 d . . . . .
H6 H 0.980(6) 0.679(3) 0.723(3) 0.028(8) Uiso 1 1 d . . . . .
H7 H 1.038(6) 0.935(3) 0.803(3) 0.026(7) Uiso 1 1 d . . . . .
H8 H 1.234(6) 0.948(3) 0.681(3) 0.023(7) Uiso 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.5 (Rigaku, 2017)'
_computing_molecular_graphics    'CrystalStructure 4.2.5'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C2 1.720(2) . ?
O1 C1 1.204(3) . ?
O2 C3 1.317(3) . ?
O2 H2 0.93(4) . ?
O3 C4 1.239(3) . ?
N1 C4 1.321(3) . ?
N1 C7 1.452(3) . ?
N1 H1 0.73(3) . ?
C1 C2 1.450(3) . ?
C1 C3 1.505(3) 2_565 ?
C2 C3 1.340(4) . ?
C3 C1 1.505(3) 2_565 ?
C4 C5 1.500(3) . ?
C5 C6 1.519(3) . ?
C5 H3 1.05(3) . ?
C5 H4 0.94(3) . ?
C6 C7 1.531(4) . ?
C6 H5 1.02(3) . ?
C6 H6 0.96(3) . ?
C7 H7 1.01(3) . ?
C7 H8 0.94(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
C3 O2 H2 117(2) . . ?
C4 N1 C7 114.6(2) . . ?
C4 N1 H1 126(2) . . ?
C7 N1 H1 119(2) . . ?
O1 C1 C2 123.8(2) . . ?
O1 C1 C3 118.6(2) . 2_565 ?
C2 C1 C3 117.6(2) . 2_565 ?
C3 C2 C1 122.3(2) . . ?
C3 C2 Cl1 121.19(19) . . ?
C1 C2 Cl1 116.46(18) . . ?
O2 C3 C2 122.8(2) . . ?
O2 C3 C1 117.2(2) . 2_565 ?
C2 C3 C1 120.0(2) . 2_565 ?
O3 C4 N1 125.3(2) . . ?
O3 C4 C5 125.8(2) . . ?
N1 C4 C5 108.9(2) . . ?
C4 C5 C6 104.6(2) . . ?
C4 C5 H3 113.1(15) . . ?
C6 C5 H3 115.0(14) . . ?
C4 C5 H4 107.9(18) . . ?
C6 C5 H4 114.5(18) . . ?
H3 C5 H4 102(2) . . ?
C5 C6 C7 104.6(2) . . ?
C5 C6 H5 114.2(16) . . ?
C7 C6 H5 110.1(16) . . ?
C5 C6 H6 109.8(18) . . ?
C7 C6 H6 108.7(19) . . ?
H5 C6 H6 109(2) . . ?
N1 C7 C6 103.1(2) . . ?
N1 C7 H7 109.6(17) . . ?
C6 C7 H7 111.2(17) . . ?
N1 C7 H8 111.5(16) . . ?
C6 C7 H8 109.4(17) . . ?
H7 C7 H8 112(2) . . ?

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
O1 C1 C2 C3 176.5(2) . . . . ?
C3 C1 C2 C3 -2.6(4) 2_565 . . . ?
O1 C1 C2 Cl1 -2.4(3) . . . . ?
C3 C1 C2 Cl1 178.50(16) 2_565 . . . ?
C1 C2 C3 O2 -178.4(2) . . . . ?
Cl1 C2 C3 O2 0.5(4) . . . . ?
C1 C2 C3 C1 2.6(4) . . . 2_565 ?
Cl1 C2 C3 C1 -178.50(17) . . . 2_565 ?
C7 N1 C4 O3 -177.4(2) . . . . ?
C7 N1 C4 C5 2.0(3) . . . . ?
O3 C4 C5 C6 -169.5(2) . . . . ?
N1 C4 C5 C6 11.1(3) . . . . ?
C4 C5 C6 C7 -18.8(3) . . . . ?
C4 N1 C7 C6 -14.0(3) . . . . ?
C5 C6 C7 N1 19.6(3) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

_shelxl_version_number           2014-3


####################################################################### 
# 
# 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_HighA
_audit_block_doi                 10.5517/ccdc.csd.cc1zq40v
_database_code_depnum_ccdc_archive 'CCDC 1838517'
_audit_update_record             
;
2018-04-20 deposited with the CCDC.
2018-06-15 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C14 H16 Cl2 N2 O6'
_chemical_formula_moiety         'C14 H16 Cl2 N2 O6'
_chemical_formula_weight         379.20
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   8.1575(9)
_cell_length_b                   10.3671(12)
_cell_length_c                   11.0921(13)
_cell_angle_alpha                74.290(5)
_cell_angle_beta                 75.655(5)
_cell_angle_gamma                67.442(5)
_cell_volume                     822.93(17)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7027
_cell_measurement_theta_min      1.91
_cell_measurement_theta_max      27.18
_cell_measurement_temperature    298
#------------------------------------------------------------------------------
_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.530
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             392.00
_exptl_absorpt_coefficient_mu    0.410
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.722
_exptl_absorpt_correction_T_max  1.000

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      298
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.703010
_diffrn_measurement_device_type  'Rigaku R-AXIS IV'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 14.706
_diffrn_reflns_number            10883
_diffrn_reflns_av_R_equivalents  0.0603
_diffrn_reflns_theta_max         27.161
_diffrn_reflns_theta_min         1.912
_diffrn_reflns_theta_full        24.948
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3744
_reflns_number_gt                2096
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0988
_refine_ls_R_factor_gt           0.0491
_refine_ls_wR_factor_ref         0.1333
_refine_ls_wR_factor_gt          0.1131
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_number_reflns         3744
_refine_ls_number_parameters     281
_refine_ls_goodness_of_fit_ref   0.946
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0625P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.25
_refine_diff_density_min         -0.24
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Cl Cl 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.01946(9) 0.91448(7) 0.29752(7) 0.0614(3) Uani 1 1 d . . . . .
Cl2 Cl 0.57807(9) 0.29329(7) 0.40835(6) 0.0539(2) Uani 1 1 d . . . . .
O1 O 0.3438(3) 0.78090(19) 0.12180(17) 0.0564(5) Uani 1 1 d . . . . .
O2 O 0.0098(3) 0.6868(2) 0.52245(18) 0.0698(6) Uani 1 1 d . . . . .
O3 O 0.2499(3) 0.4255(2) 0.58217(17) 0.0562(5) Uani 1 1 d . . . . .
O4 O 0.5737(3) 0.5143(2) 0.17592(17) 0.0679(6) Uani 1 1 d . . . . .
O5 O 0.5923(3) 0.7019(2) -0.06473(17) 0.0675(6) Uani 1 1 d . . . . .
O6 O -0.0228(2) 0.49973(19) 0.75802(16) 0.0575(5) Uani 1 1 d . . . . .
N1 N 0.7092(3) 0.7863(3) -0.2648(2) 0.0483(6) Uani 1 1 d . . . . .
N2 N -0.1365(3) 0.4151(3) 0.9599(2) 0.0508(6) Uani 1 1 d . . . . .
C1 C 0.3135(3) 0.6986(3) 0.2327(2) 0.0430(6) Uani 1 1 d . . . . .
C2 C 0.1724(3) 0.7446(3) 0.3219(2) 0.0426(6) Uani 1 1 d . . . . .
C3 C 0.1396(3) 0.6518(3) 0.4427(2) 0.0446(6) Uani 1 1 d . . . . .
C4 C 0.2754(3) 0.5048(3) 0.4691(2) 0.0415(6) Uani 1 1 d . . . . .
C5 C 0.4172(3) 0.4602(3) 0.3803(2) 0.0412(6) Uani 1 1 d . . . . .
C6 C 0.4469(3) 0.5496(3) 0.2581(2) 0.0422(6) Uani 1 1 d . . . . .
C7 C 0.6767(4) 0.9133(3) -0.3638(3) 0.0560(8) Uani 1 1 d . . . . .
C8 C 0.5152(6) 1.0189(5) -0.3025(4) 0.0899(15) Uani 1 1 d . . . . .
C9 C 0.4576(5) 0.9454(3) -0.1739(3) 0.0638(9) Uani 1 1 d . . . . .
C10 C 0.5915(3) 0.7970(3) -0.1602(2) 0.0466(6) Uani 1 1 d . . . . .
C11 C -0.0917(5) 0.2935(3) 1.0633(3) 0.0561(8) Uani 1 1 d . . . . .
C12 C 0.0622(5) 0.1832(3) 0.9989(3) 0.0603(8) Uani 1 1 d . . . . .
C13 C 0.1367(4) 0.2692(3) 0.8780(3) 0.0523(7) Uani 1 1 d . . . . .
C14 C -0.0140(3) 0.4070(3) 0.8568(2) 0.0435(6) Uani 1 1 d . . . . .
H1 H 0.435(5) 0.734(3) 0.062(3) 0.097(12) Uiso 1 1 d . . . . .
H2 H 0.160(5) 0.464(4) 0.635(3) 0.107(14) Uiso 1 1 d . . . . .
H3 H 0.789(4) 0.721(3) -0.275(3) 0.058(10) Uiso 1 1 d . . . . .
H4 H 0.659(4) 0.896(3) -0.442(3) 0.072(9) Uiso 1 1 d . . . . .
H5 H 0.778(4) 0.949(3) -0.392(3) 0.069(9) Uiso 1 1 d . . . . .
H6 H 0.484(5) 1.099(4) -0.324(4) 0.101(15) Uiso 1 1 d . . . . .
H7 H 0.408(7) 1.033(6) -0.354(5) 0.19(2) Uiso 1 1 d . . . . .
H8 H 0.347(5) 0.940(4) -0.163(4) 0.117(16) Uiso 1 1 d . . . . .
H9 H 0.446(6) 0.983(5) -0.106(4) 0.136(17) Uiso 1 1 d . . . . .
H10 H -0.217(3) 0.478(3) 0.970(2) 0.044(8) Uiso 1 1 d . . . . .
H11 H -0.189(3) 0.255(3) 1.101(2) 0.054(8) Uiso 1 1 d . . . . .
H12 H -0.052(4) 0.317(3) 1.127(3) 0.082(11) Uiso 1 1 d . . . . .
H13 H 0.151(4) 0.125(3) 1.055(3) 0.071(9) Uiso 1 1 d . . . . .
H14 H 0.018(4) 0.114(4) 0.981(3) 0.099(12) Uiso 1 1 d . . . . .
H15 H 0.177(4) 0.224(3) 0.805(3) 0.076(10) Uiso 1 1 d . . . . .
H16 H 0.237(4) 0.287(3) 0.889(3) 0.065(9) Uiso 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.5 (Rigaku, 2017)'
_computing_molecular_graphics    'CrystalStructure 4.2.5'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C2 1.719(2) . ?
Cl2 C5 1.727(2) . ?
O1 C1 1.320(3) . ?
O1 H1 0.94(4) . ?
O2 C3 1.204(3) . ?
O3 C4 1.317(3) . ?
O3 H2 0.85(4) . ?
O4 C6 1.208(3) . ?
O5 C10 1.236(3) . ?
O6 C14 1.243(3) . ?
N1 C10 1.311(3) . ?
N1 C7 1.451(3) . ?
N1 H3 0.75(3) . ?
N2 C14 1.317(3) . ?
N2 C11 1.453(3) . ?
N2 H10 0.74(3) . ?
C1 C2 1.342(3) . ?
C1 C6 1.508(3) . ?
C2 C3 1.454(3) . ?
C3 C4 1.503(3) . ?
C4 C5 1.339(3) . ?
C5 C6 1.444(3) . ?
C7 C8 1.500(4) . ?
C7 H4 0.99(3) . ?
C7 H5 0.98(3) . ?
C8 C9 1.480(4) . ?
C8 H6 0.76(4) . ?
C8 H7 1.10(5) . ?
C9 C10 1.500(4) . ?
C9 H8 0.90(4) . ?
C9 H9 0.91(4) . ?
C11 C12 1.513(4) . ?
C11 H11 0.97(2) . ?
C11 H12 0.96(3) . ?
C12 C13 1.526(4) . ?
C12 H13 0.98(3) . ?
C12 H14 1.00(3) . ?
C13 C14 1.490(4) . ?
C13 H15 0.97(3) . ?
C13 H16 0.95(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
C1 O1 H1 115(2) . . ?
C4 O3 H2 117(3) . . ?
C10 N1 C7 115.0(2) . . ?
C10 N1 H3 124(2) . . ?
C7 N1 H3 121(2) . . ?
C14 N2 C11 114.4(2) . . ?
C14 N2 H10 125(2) . . ?
C11 N2 H10 120(2) . . ?
O1 C1 C2 122.2(2) . . ?
O1 C1 C6 117.5(2) . . ?
C2 C1 C6 120.2(2) . . ?
C1 C2 C3 121.4(2) . . ?
C1 C2 Cl1 121.7(2) . . ?
C3 C2 Cl1 116.89(18) . . ?
O2 C3 C2 123.4(2) . . ?
O2 C3 C4 118.5(2) . . ?
C2 C3 C4 118.1(2) . . ?
O3 C4 C5 122.6(2) . . ?
O3 C4 C3 117.3(2) . . ?
C5 C4 C3 120.0(2) . . ?
C4 C5 C6 122.2(2) . . ?
C4 C5 Cl2 121.3(2) . . ?
C6 C5 Cl2 116.46(18) . . ?
O4 C6 C5 124.3(2) . . ?
O4 C6 C1 117.7(2) . . ?
C5 C6 C1 117.9(2) . . ?
N1 C7 C8 103.2(2) . . ?
N1 C7 H4 112.1(17) . . ?
C8 C7 H4 113.8(18) . . ?
N1 C7 H5 113.7(17) . . ?
C8 C7 H5 110.5(17) . . ?
H4 C7 H5 104(2) . . ?
C9 C8 C7 107.9(3) . . ?
C9 C8 H6 124(3) . . ?
C7 C8 H6 126(3) . . ?
C9 C8 H7 102(3) . . ?
C7 C8 H7 103(3) . . ?
H6 C8 H7 81(3) . . ?
C8 C9 C10 105.1(3) . . ?
C8 C9 H8 114(2) . . ?
C10 C9 H8 109(3) . . ?
C8 C9 H9 119(3) . . ?
C10 C9 H9 110(3) . . ?
H8 C9 H9 100(3) . . ?
O5 C10 N1 125.8(2) . . ?
O5 C10 C9 125.4(2) . . ?
N1 C10 C9 108.7(2) . . ?
N2 C11 C12 103.0(2) . . ?
N2 C11 H11 113.5(16) . . ?
C12 C11 H11 108.7(16) . . ?
N2 C11 H12 110.3(19) . . ?
C12 C11 H12 110.0(19) . . ?
H11 C11 H12 111(2) . . ?
C11 C12 C13 104.6(2) . . ?
C11 C12 H13 111.1(17) . . ?
C13 C12 H13 114.2(17) . . ?
C11 C12 H14 110(2) . . ?
C13 C12 H14 112.2(19) . . ?
H13 C12 H14 104(3) . . ?
C14 C13 C12 104.0(2) . . ?
C14 C13 H15 111.9(19) . . ?
C12 C13 H15 114.3(18) . . ?
C14 C13 H16 109.0(17) . . ?
C12 C13 H16 111.4(16) . . ?
H15 C13 H16 106(2) . . ?
O6 C14 N2 125.3(2) . . ?
O6 C14 C13 125.6(2) . . ?
N2 C14 C13 109.0(2) . . ?

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
O1 C1 C2 C3 179.0(2) . . . . ?
C6 C1 C2 C3 -2.5(4) . . . . ?
O1 C1 C2 Cl1 0.4(4) . . . . ?
C6 C1 C2 Cl1 178.97(18) . . . . ?
C1 C2 C3 O2 -176.2(3) . . . . ?
Cl1 C2 C3 O2 2.5(4) . . . . ?
C1 C2 C3 C4 4.1(4) . . . . ?
Cl1 C2 C3 C4 -177.30(19) . . . . ?
O2 C3 C4 O3 -4.2(4) . . . . ?
C2 C3 C4 O3 175.6(2) . . . . ?
O2 C3 C4 C5 177.1(3) . . . . ?
C2 C3 C4 C5 -3.1(4) . . . . ?
O3 C4 C5 C6 -178.0(2) . . . . ?
C3 C4 C5 C6 0.6(4) . . . . ?
O3 C4 C5 Cl2 0.2(4) . . . . ?
C3 C4 C5 Cl2 178.80(18) . . . . ?
C4 C5 C6 O4 179.2(3) . . . . ?
Cl2 C5 C6 O4 0.9(4) . . . . ?
C4 C5 C6 C1 1.0(4) . . . . ?
Cl2 C5 C6 C1 -177.22(18) . . . . ?
O1 C1 C6 O4 0.2(4) . . . . ?
C2 C1 C6 O4 -178.4(3) . . . . ?
O1 C1 C6 C5 178.5(2) . . . . ?
C2 C1 C6 C5 -0.1(4) . . . . ?
C10 N1 C7 C8 3.1(4) . . . . ?
N1 C7 C8 C9 -2.8(5) . . . . ?
C7 C8 C9 C10 1.7(5) . . . . ?
C7 N1 C10 O5 179.3(3) . . . . ?
C7 N1 C10 C9 -2.1(4) . . . . ?
C8 C9 C10 O5 178.8(4) . . . . ?
C8 C9 C10 N1 0.1(5) . . . . ?
C14 N2 C11 C12 -14.5(4) . . . . ?
N2 C11 C12 C13 21.1(4) . . . . ?
C11 C12 C13 C14 -20.8(4) . . . . ?
C11 N2 C14 O6 -178.7(3) . . . . ?
C11 N2 C14 C13 1.1(4) . . . . ?
C12 C13 C14 O6 -167.5(3) . . . . ?
C12 C13 C14 N2 12.7(4) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

_shelxl_version_number           2014-3


