# 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_1_(2,3)_shelx
_database_code_depnum_ccdc_archive 'CCDC 1478072'
_audit_update_record             
;
2016-05-04 deposited with the CCDC.
2016-06-13 downloaded from the CCDC.
;

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         
;
C6 H Cl2 O4, C7 H10 N                                                        
;
_chemical_formula_sum            'C13 H11 Cl2 N O4'
_chemical_formula_weight         316.13
_chemical_compound_source        commercial
#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_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_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   3.8653(4)
_cell_length_b                   11.5522(12)
_cell_length_c                   14.4711(14)
_cell_angle_alpha                98.976(6)
_cell_angle_beta                 93.377(5)
_cell_angle_gamma                91.025(6)
_cell_volume                     636.91(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3793
_cell_measurement_theta_min      1.427
_cell_measurement_theta_max      30.399
_cell_measurement_wavelength     0.71073
#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_exptl_crystal_density_diffrn    1.648
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             324
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.522
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.685
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   'SADABS, Bruker(2001)'
#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'APEX-II CCD'
_diffrn_orient_matrix_type       'x-axis to radiation source'
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'φ or ω oscillation scans'
_diffrn_orient_matrix_UB_11      0.705993E-1
_diffrn_orient_matrix_UB_12      0.801366E-1
_diffrn_orient_matrix_UB_13      -0.111194E-1
_diffrn_orient_matrix_UB_21      -0.298253E-1
_diffrn_orient_matrix_UB_22      -0.266529E-1
_diffrn_orient_matrix_UB_23      -0.692069E-1
_diffrn_orient_matrix_UB_31      -0.24767
_diffrn_orient_matrix_UB_32      0.235318E-1
_diffrn_orient_matrix_UB_33      0.580792E-3
_diffrn_reflns_av_R_equivalents  0.0855
_diffrn_reflns_av_unetI/netI     0.0727
_diffrn_reflns_number            3793
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.43
_diffrn_reflns_theta_max         30.4
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.981
_reflns_Friedel_coverage         0
_reflns_number_total             3793
_reflns_number_gt                2758
_reflns_threshold_expression     'I > 2σ(I)'
#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 software'
_computing_cell_refinement       'SAINT V7.68A integration software'
_computing_data_reduction        'SORTAV (Blessing, 1995)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0362P)²+0.2792P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3793
_refine_ls_number_parameters     206
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0767
_refine_ls_R_factor_gt           0.0457
_refine_ls_wR_factor_ref         0.098
_refine_ls_wR_factor_gt          0.0909
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.438
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.08

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 -0.51252(11) -0.37127(4) -0.05479(3) 0.01592(12) Uani 1 1 d . . . . .
Cl2 Cl 0.03794(11) -0.07484(4) -0.35272(3) 0.01615(12) Uani 1 1 d . . . . .
O2 O -0.6191(3) -0.42372(12) -0.26433(9) 0.0175(3) Uani 1 1 d . . . . .
O3 O -0.3439(3) -0.30415(11) -0.38787(8) 0.0180(3) Uani 1 1 d . . . . .
O5 O 0.1056(3) -0.01246(12) -0.14590(10) 0.0173(3) Uani 1 1 d . . . . .
O6 O -0.1412(3) -0.13390(12) -0.02125(8) 0.0184(3) Uani 1 1 d . . . . .
N125 N -1.0355(4) -0.60336(14) -0.24448(10) 0.0137(3) Uani 1 1 d . . . . .
C121 C -1.2260(5) -0.75376(17) -0.16554(13) 0.0162(4) Uani 1 1 d . . . . .
C122 C -1.3636(4) -0.81355(16) -0.25111(12) 0.0150(4) Uani 1 1 d . . . . .
H122 H -1.4756 -0.8859 -0.2533 0.018 Uiso 1 1 calc R U . . .
C123 C -1.3365(4) -0.76666(16) -0.33400(12) 0.0131(4) Uani 1 1 d . . . . .
C124 C -1.1684(4) -0.65772(16) -0.32924(12) 0.0126(4) Uani 1 1 d . . . . .
C126 C -1.0592(5) -0.64753(17) -0.16429(12) 0.0159(4) Uani 1 1 d . . . . .
H126 H -0.9628 -0.6062 -0.1081 0.019 Uiso 1 1 calc R U . . .
C23 C -1.4783(5) -0.83309(17) -0.42672(12) 0.0170(4) Uani 1 1 d . . . . .
H23A H -1.6066 -0.7811 -0.4607 0.025 Uiso 1 1 calc R U . . .
H23B H -1.6285 -0.8962 -0.4161 0.025 Uiso 1 1 calc R U . . .
H23C H -1.2902 -0.8643 -0.4625 0.025 Uiso 1 1 calc R U . . .
C24 C -1.1286(5) -0.59583(18) -0.41119(13) 0.0167(4) Uani 1 1 d . . . . .
C111 C -0.3707(4) -0.28916(16) -0.13697(12) 0.0127(3) Uani 1 1 d . . . . .
C112 C -0.4455(4) -0.33303(16) -0.23193(12) 0.0124(3) Uani 1 1 d . . . . .
C113 C -0.3004(4) -0.26408(15) -0.30507(11) 0.0122(3) Uani 1 1 d . . . . .
C114 C -0.1152(4) -0.15306(16) -0.27060(12) 0.0130(3) Uani 1 1 d . . . . .
C115 C -0.0655(4) -0.11278(16) -0.17773(12) 0.0133(4) Uani 1 1 d . . . . .
C116 C -0.1971(4) -0.18048(16) -0.10457(12) 0.0129(3) Uani 1 1 d . . . . .
H121 H -1.237(5) -0.7886(19) -0.1126(15) 0.017(5) Uiso 1 1 d . . . . .
H125 H -0.924(6) -0.538(2) -0.2426(16) 0.025(6) Uiso 1 1 d . . . . .
H24A H -0.976(7) -0.528(2) -0.3953(18) 0.039(7) Uiso 1 1 d . . . . .
H24B H -1.063(6) -0.644(2) -0.4624(18) 0.032(6) Uiso 1 1 d . . . . .
H24C H -1.333(7) -0.569(2) -0.4318(19) 0.046(8) Uiso 1 1 d . . . . .
H5 H 0.097(7) 0.000(2) -0.0904(19) 0.038(7) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   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 C111 1.7392(18) . ?
Cl2 C114 1.7258(18) . ?
O2 C112 1.246(2) . ?
O3 C113 1.216(2) . ?
O5 C115 1.328(2) . ?
O5 H5 0.80(3) . ?
O6 C116 1.246(2) . ?
N125 C126 1.346(2) . ?
N125 C124 1.355(2) . ?
N125 H125 0.86(2) . ?
C121 C126 1.373(3) . ?
C121 C122 1.391(3) . ?
C121 H121 0.92(2) . ?
C122 C123 1.399(2) . ?
C122 H122 0.93 . ?
C123 C124 1.396(3) . ?
C123 C23 1.506(2) . ?
C124 C24 1.491(3) . ?
C126 H126 0.93 . ?
C23 H23A 0.96 . ?
C23 H23B 0.96 . ?
C23 H23C 0.96 . ?
C24 H24A 0.96(3) . ?
C24 H24B 0.91(2) . ?
C24 H24C 0.90(3) . ?
C111 C112 1.400(2) . ?
C111 C116 1.413(2) . ?
C112 C113 1.545(2) . ?
C113 C114 1.460(3) . ?
C114 C115 1.353(2) . ?
C115 C116 1.516(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
C115 O5 H5 108.2(19) . . ?
C126 N125 C124 123.89(17) . . ?
C126 N125 H125 118.5(15) . . ?
C124 N125 H125 117.5(15) . . ?
C126 C121 C122 118.33(17) . . ?
C126 C121 H121 122.3(13) . . ?
C122 C121 H121 119.2(14) . . ?
C121 C122 C123 121.16(17) . . ?
C121 C122 H122 119.4 . . ?
C123 C122 H122 119.4 . . ?
C124 C123 C122 118.55(16) . . ?
C124 C123 C23 120.53(16) . . ?
C122 C123 C23 120.91(17) . . ?
N125 C124 C123 118.16(16) . . ?
N125 C124 C24 117.43(16) . . ?
C123 C124 C24 124.40(16) . . ?
N125 C126 C121 119.91(17) . . ?
N125 C126 H126 120 . . ?
C121 C126 H126 120 . . ?
C123 C23 H23A 109.5 . . ?
C123 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C123 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C124 C24 H24A 111.5(16) . . ?
C124 C24 H24B 112.5(16) . . ?
H24A C24 H24B 112(2) . . ?
C124 C24 H24C 111.7(18) . . ?
H24A C24 H24C 106(2) . . ?
H24B C24 H24C 103(2) . . ?
C112 C111 C116 123.57(16) . . ?
C112 C111 Cl1 117.88(13) . . ?
C116 C111 Cl1 118.52(13) . . ?
O2 C112 C111 126.35(17) . . ?
O2 C112 C113 115.73(15) . . ?
C111 C112 C113 117.92(15) . . ?
O3 C113 C114 123.14(16) . . ?
O3 C113 C112 119.11(16) . . ?
C114 C113 C112 117.74(14) . . ?
C115 C114 C113 121.33(16) . . ?
C115 C114 Cl2 121.13(14) . . ?
C113 C114 Cl2 117.54(13) . . ?
O5 C115 C114 121.63(16) . . ?
O5 C115 C116 116.50(15) . . ?
C114 C115 C116 121.87(16) . . ?
O6 C116 C111 126.43(17) . . ?
O6 C116 C115 116.21(16) . . ?
C111 C116 C115 117.36(15) . . ?

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
C126 C121 C122 C123 -0.6(3) . . . . ?
C121 C122 C123 C124 -0.2(3) . . . . ?
C121 C122 C123 C23 178.51(16) . . . . ?
C126 N125 C124 C123 -0.8(2) . . . . ?
C126 N125 C124 C24 178.42(17) . . . . ?
C122 C123 C124 N125 0.9(2) . . . . ?
C23 C123 C124 N125 -177.85(15) . . . . ?
C122 C123 C124 C24 -178.30(16) . . . . ?
C23 C123 C124 C24 3.0(3) . . . . ?
C124 N125 C126 C121 0.0(3) . . . . ?
C122 C121 C126 N125 0.7(3) . . . . ?
C116 C111 C112 O2 -174.39(17) . . . . ?
Cl1 C111 C112 O2 3.4(3) . . . . ?
C116 C111 C112 C113 5.8(3) . . . . ?
Cl1 C111 C112 C113 -176.32(12) . . . . ?
O2 C112 C113 O3 -4.2(2) . . . . ?
C111 C112 C113 O3 175.56(16) . . . . ?
O2 C112 C113 C114 175.94(15) . . . . ?
C111 C112 C113 C114 -4.3(2) . . . . ?
O3 C113 C114 C115 -178.47(16) . . . . ?
C112 C113 C114 C115 1.4(2) . . . . ?
O3 C113 C114 Cl2 1.6(2) . . . . ?
C112 C113 C114 Cl2 -178.60(11) . . . . ?
C113 C114 C115 O5 179.33(15) . . . . ?
Cl2 C114 C115 O5 -0.7(2) . . . . ?
C113 C114 C115 C116 0.2(3) . . . . ?
Cl2 C114 C115 C116 -179.80(12) . . . . ?
C112 C111 C116 O6 175.59(17) . . . . ?
Cl1 C111 C116 O6 -2.2(3) . . . . ?
C112 C111 C116 C115 -4.2(3) . . . . ?
Cl1 C111 C116 C115 177.93(12) . . . . ?
O5 C115 C116 O6 2.0(2) . . . . ?
C114 C115 C116 O6 -178.86(16) . . . . ?
O5 C115 C116 C111 -178.13(15) . . . . ?
C114 C115 C116 C111 1.0(2) . . . . ?

####################################################################### 
# 
# 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_2_(2,3)_shelx
_database_code_depnum_ccdc_archive 'CCDC 1478073'
_audit_update_record             
;
2016-05-04 deposited with the CCDC.
2016-06-13 downloaded from the CCDC.
;

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         
;
C6 Cl2 O4, 2(C7 H10 N)  
;
_chemical_formula_sum            'C20 H20 Cl2 N2 O4'
_chemical_formula_weight         423.28
_chemical_compound_source        commercial
#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_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_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.6305(2)
_cell_length_b                   8.3081(2)
_cell_length_c                   8.4348(2)
_cell_angle_alpha                65.8390(10)
_cell_angle_beta                 80.610(2)
_cell_angle_gamma                88.2800(10)
_cell_volume                     480.94(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    10130
_cell_measurement_theta_min      2.684
_cell_measurement_theta_max      50.437
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             220
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.368
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5024
_exptl_absorpt_correction_T_max  0.7496
_exptl_absorpt_process_details   'SADABS, Bruker(2001)'
#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      -0.183826E-1
_diffrn_orient_matrix_UB_21      -0.796826E-1
_diffrn_orient_matrix_UB_31      0.1048182
_diffrn_orient_matrix_UB_12      0.409594E-1
_diffrn_orient_matrix_UB_22      0.927704E-1
_diffrn_orient_matrix_UB_32      0.845478E-1
_diffrn_orient_matrix_UB_13      -0.1250751
_diffrn_orient_matrix_UB_23      0.138881E-1
_diffrn_orient_matrix_UB_33      -0.390228E-1
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_number            10130
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.684
_diffrn_reflns_theta_max         50.437
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.985
_reflns_Friedel_coverage         0
_reflns_number_total             10130
_reflns_number_gt                9201
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
 Scaled and merged with Sortav
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0503P)²+0.0161P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_number_reflns         10130
_refine_ls_number_parameters     167
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0295
_refine_ls_R_factor_gt           0.0266
_refine_ls_wR_factor_ref         0.0828
_refine_ls_wR_factor_gt          0.0813
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.654
_refine_diff_density_min         -0.28
_refine_diff_density_rms         0.063
#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.58555(2) 0.60521(2) 0.23964(2) 0.01557(2) Uani 1 1 d . . . . .
O2 O 0.34437(4) 0.72625(3) -0.03107(3) 0.01684(4) Uani 1 1 d . . . . .
O3 O 0.28146(4) 1.05846(3) -0.23667(4) 0.01799(4) Uani 1 1 d . . . . .
N125 N 0.09485(3) 0.74908(4) -0.22420(3) 0.01482(3) Uani 1 1 d . . . . .
C121 C -0.20314(4) 0.67317(4) -0.21872(4) 0.01671(4) Uani 1 1 d . . . . .
C122 C -0.15630(4) 0.69510(5) -0.39403(4) 0.01643(4) Uani 1 1 d . . . . .
C123 C 0.01787(4) 0.74386(4) -0.48363(4) 0.01445(4) Uani 1 1 d . . . . .
C124 C 0.14429(4) 0.77196(4) -0.39292(4) 0.01331(3) Uani 1 1 d . . . . .
C126 C -0.07266(4) 0.70149(5) -0.13607(4) 0.01660(4) Uani 1 1 d . . . . .
C23 C 0.07209(5) 0.76377(6) -0.67064(5) 0.02125(5) Uani 1 1 d . . . . .
C24 C 0.33391(4) 0.82795(5) -0.47514(5) 0.01784(4) Uani 1 1 d . . . . .
C111 C 0.54118(4) 0.82094(3) 0.10454(3) 0.01228(3) Uani 1 1 d . . . . .
C112 C 0.42198(3) 0.84731(3) -0.01210(3) 0.01207(3) Uani 1 1 d . . . . .
C113 C 0.38030(3) 1.03903(4) -0.12785(3) 0.01219(3) Uani 1 1 d . . . . .
H121 H -0.3242(13) 0.6407(14) -0.1539(13) 0.029(2) Uiso 1 1 d . . . . .
H122 H -0.2438(13) 0.6809(13) -0.4548(12) 0.026(2) Uiso 1 1 d . . . . .
H125 H 0.1859(16) 0.7663(17) -0.1601(16) 0.048(3) Uiso 1 1 d . . . . .
H126 H -0.0891(13) 0.6838(13) -0.0153(12) 0.026(2) Uiso 1 1 d . . . . .
H23A H 0.1745(14) 0.6896(15) -0.6855(14) 0.035(2) Uiso 1 1 d . . . . .
H23B H -0.0323(15) 0.7329(15) -0.7164(15) 0.040(3) Uiso 1 1 d . . . . .
H23C H 0.1068(16) 0.8858(16) -0.7527(16) 0.042(3) Uiso 1 1 d . . . . .
H24A H 0.4023(15) 0.8343(16) -0.3884(15) 0.040(3) Uiso 1 1 d . . . . .
H24B H 0.3815(12) 0.7480(13) -0.5215(12) 0.026(2) Uiso 1 1 d . . . . .
H24C H 0.3362(15) 0.9502(16) -0.5679(15) 0.038(3) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   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 C111 1.7444(3) . ?
O2 C112 1.2595(3) . ?
O3 C113 1.2388(3) . ?
N125 C124 1.3459(4) . ?
N125 C126 1.3499(4) . ?
N125 H125 0.994(12) . ?
C121 C126 1.3812(4) . ?
C121 C122 1.3994(5) . ?
C121 H121 0.977(10) . ?
C122 C123 1.3984(4) . ?
C122 H122 0.942(10) . ?
C123 C124 1.4040(4) . ?
C123 C23 1.5047(5) . ?
C124 C24 1.4966(4) . ?
C126 H126 0.955(9) . ?
C23 H23A 1.004(11) . ?
C23 H23B 1.021(11) . ?
C23 H23C 0.979(12) . ?
C24 H24A 0.984(12) . ?
C24 H24B 0.937(9) . ?
C24 H24C 0.995(12) . ?
C111 C112 1.3953(4) . ?
C111 C113 1.4207(4) 2_675 ?
C112 C113 1.5458(4) . ?
C113 C111 1.4208(4) 2_675 ?

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
C124 N125 C126 123.26(3) . . ?
C124 N125 H125 118.8(7) . . ?
C126 N125 H125 117.9(7) . . ?
C126 C121 C122 118.23(3) . . ?
C126 C121 H121 119.2(6) . . ?
C122 C121 H121 122.6(6) . . ?
C123 C122 C121 121.13(3) . . ?
C123 C122 H122 118.9(6) . . ?
C121 C122 H122 119.9(6) . . ?
C122 C123 C124 117.98(3) . . ?
C122 C123 C23 121.99(3) . . ?
C124 C123 C23 120.02(3) . . ?
N125 C124 C123 119.34(2) . . ?
N125 C124 C24 117.54(3) . . ?
C123 C124 C24 123.12(3) . . ?
N125 C126 C121 120.07(3) . . ?
N125 C126 H126 115.0(6) . . ?
C121 C126 H126 124.8(6) . . ?
C123 C23 H23A 113.2(6) . . ?
C123 C23 H23B 110.9(6) . . ?
H23A C23 H23B 108.8(9) . . ?
C123 C23 H23C 112.6(7) . . ?
H23A C23 H23C 106.7(9) . . ?
H23B C23 H23C 104.1(9) . . ?
C124 C24 H24A 110.6(7) . . ?
C124 C24 H24B 108.5(6) . . ?
H24A C24 H24B 111.5(9) . . ?
C124 C24 H24C 108.0(6) . . ?
H24A C24 H24C 106.1(9) . . ?
H24B C24 H24C 112.0(9) . . ?
C112 C111 C113 123.27(2) . 2_675 ?
C112 C111 Cl1 118.73(2) . . ?
C113 C111 Cl1 117.855(19) 2_675 . ?
O2 C112 C111 125.03(3) . . ?
O2 C112 C113 116.74(2) . . ?
C111 C112 C113 118.23(2) . . ?
O3 C113 C111 124.86(3) . 2_675 ?
O3 C113 C112 116.70(2) . . ?
C111 C113 C112 118.44(2) 2_675 . ?

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
C126 C121 C122 C123 0.19(5) . . . . ?
C121 C122 C123 C124 -0.63(5) . . . . ?
C121 C122 C123 C23 178.46(3) . . . . ?
C126 N125 C124 C123 -0.69(5) . . . . ?
C126 N125 C124 C24 178.95(3) . . . . ?
C122 C123 C124 N125 0.86(4) . . . . ?
C23 C123 C124 N125 -178.24(3) . . . . ?
C122 C123 C124 C24 -178.76(3) . . . . ?
C23 C123 C124 C24 2.14(5) . . . . ?
C124 N125 C126 C121 0.23(5) . . . . ?
C122 C121 C126 N125 0.03(5) . . . . ?
C113 C111 C112 O2 -176.99(3) 2_675 . . . ?
Cl1 C111 C112 O2 -1.40(4) . . . . ?
C113 C111 C112 C113 2.95(4) 2_675 . . . ?
Cl1 C111 C112 C113 178.536(18) . . . . ?
O2 C112 C113 O3 -3.80(4) . . . . ?
C111 C112 C113 O3 176.26(3) . . . . ?
O2 C112 C113 C111 177.14(3) . . . 2_675 ?
C111 C112 C113 C111 -2.80(4) . . . 2_675 ?

####################################################################### 
# 
# 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_2_(2,3)_xd
_database_code_depnum_ccdc_archive 'CCDC 1478074'
_audit_update_record             
;
2016-05-04 deposited with the CCDC.
2016-06-13 downloaded from the CCDC.
;

_chemical_formula_moiety         
;
C6 Cl2 O4, 2(C7 H10 N)  
;
_chemical_formula_sum            'C20 H20 Cl2 N2 O4'
_chemical_formula_weight         423.28
_chemical_compound_source        commercial

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#
_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                   7.6305(2)
_cell_length_b                   8.3081(2)
_cell_length_c                   8.4348(2)
_cell_angle_alpha                65.8390(10)
_cell_angle_beta                 80.610(2)
_cell_angle_gamma                88.2800(10)
_cell_volume                     480.94(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    10134
_cell_measurement_theta_min      1
_cell_measurement_theta_max      50.44
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             220
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.368
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5024
_exptl_absorpt_correction_T_max  0.7496
_exptl_absorpt_process_details   'SADABS, Bruker(2001)'
#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      -0.183826E-1
_diffrn_orient_matrix_UB_21      -0.796826E-1
_diffrn_orient_matrix_UB_31      0.1048182
_diffrn_orient_matrix_UB_12      0.409594E-1
_diffrn_orient_matrix_UB_22      0.927704E-1
_diffrn_orient_matrix_UB_32      0.845478E-1
_diffrn_orient_matrix_UB_13      -0.1250751
_diffrn_orient_matrix_UB_23      0.138881E-1
_diffrn_orient_matrix_UB_33      -0.390228E-1
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_number            10134
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.68
_diffrn_reflns_theta_max         50.44
_diffrn_reflns_theta_full        50.44
_diffrn_measured_fraction_theta_full 0.985

_diffrn_measured_fraction_theta_max 0.985

_reflns_number_total             10134
_reflns_number_gt                9205
_reflns_threshold_expression     >2σ(I)
_diffrn_reflns_reduction_process 
;
 Scaled and merged with Sortav
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
        ?
;
_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
        calc w1 = 1/[s²(Fo)]
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_extinction_method     none
_refine_ls_number_reflns         9384
_refine_ls_number_parameters     378
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.021
_refine_ls_R_factor_gt           0.017
_refine_ls_wR_factor_ref         0.022
_refine_ls_goodness_of_fit_ref   1.33
_refine_ls_shift/su_max          0
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.033

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, 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_symmetry_multiplicity
Cl(1) Cl 0.585539(6) 0.605220(6) 0.239634(6) 0.016 Uani 1 2
O(2) O 0.34440(3) 0.72629(3) -0.03099(3) 0.017 Uani 1 2
O(3) O 0.28175(3) 1.05847(3) -0.23685(3) 0.018 Uani 1 2
N(125) N 0.09486(3) 0.74911(3) -0.22413(3) 0.015 Uani 1 2
C(121) C -0.20323(3) 0.67313(3) -0.21865(3) 0.017 Uani 1 2
C(122) C -0.15625(3) 0.69510(3) -0.39416(3) 0.016 Uani 1 2
C(123) C 0.01791(3) 0.74390(3) -0.48362(3) 0.014 Uani 1 2
C(124) C 0.14436(2) 0.77196(2) -0.39291(2) 0.013 Uani 1 2
C(126) C -0.07255(3) 0.70151(3) -0.13604(3) 0.017 Uani 1 2
C(23) C 0.07212(3) 0.76371(4) -0.67055(3) 0.021 Uani 1 2
C(24) C 0.33385(3) 0.82781(3) -0.47499(3) 0.018 Uani 1 2
C(111) C 0.54120(2) 0.82089(2) 0.10460(2) 0.012 Uani 1 2
C(112) C 0.42195(2) 0.84734(2) -0.01211(2) 0.012 Uani 1 2
C(113) C 0.38028(2) 1.03903(2) -0.12783(2) 0.012 Uani 1 2
H(121) H -0.337488 0.636326 -0.14716 0.034 Uani 1 2
H(122) H -0.256207 0.678403 -0.464383 0.031 Uani 1 2
H(125) H 0.190479 0.767311 -0.15862 0.027 Uani 1 2
H(126) H -0.090519 0.682613 0.000568 0.032 Uani 1 2
H(23A) H 0.17862 0.68364 -0.685467 0.04 Uani 1 2
H(23B) H -0.035003 0.732032 -0.71965 0.039 Uani 1 2
H(23C) H 0.1095 0.895505 -0.759929 0.039 Uani 1 2
H(24A) H 0.409276 0.83485 -0.383008 0.035 Uani 1 2
H(24B) H 0.388249 0.739502 -0.529838 0.038 Uani 1 2
H(24C) H 0.335679 0.957832 -0.573749 0.037 Uani 1 2



#----------------------------------------------------------------------------#
#                   MULTIPOLE PARAMETERS                                     #
#----------------------------------------------------------------------------#

loop_
_atom_rho_multipole_atom_label
_atom_rho_multipole_coeff_Pv
_atom_rho_multipole_coeff_P00
_atom_rho_multipole_coeff_P11
_atom_rho_multipole_coeff_P1-1
_atom_rho_multipole_coeff_P10
_atom_rho_multipole_coeff_P20
_atom_rho_multipole_coeff_P21
_atom_rho_multipole_coeff_P2-1
_atom_rho_multipole_coeff_P22
_atom_rho_multipole_coeff_P2-2
_atom_rho_multipole_coeff_P30
_atom_rho_multipole_coeff_P31
_atom_rho_multipole_coeff_P3-1
_atom_rho_multipole_coeff_P32
_atom_rho_multipole_coeff_P3-2
_atom_rho_multipole_coeff_P33
_atom_rho_multipole_coeff_P3-3
_atom_rho_multipole_coeff_P40
_atom_rho_multipole_coeff_P41
_atom_rho_multipole_coeff_P4-1
_atom_rho_multipole_coeff_P42
_atom_rho_multipole_coeff_P4-2
_atom_rho_multipole_coeff_P43
_atom_rho_multipole_coeff_P4-3
_atom_rho_multipole_coeff_P44
_atom_rho_multipole_coeff_P4-4
_atom_rho_multipole_kappa
_atom_rho_multipole_kappa_prime0
_atom_rho_multipole_kappa_prime1
_atom_rho_multipole_kappa_prime2
_atom_rho_multipole_kappa_prime3
_atom_rho_multipole_kappa_prime4
Cl(1) 7.42(2) 0 0.029(8) 0.007(8) -0.035(9) -0.064(14) 0.016(12) -0.039(13)
-0.007(12) 0.001(13) 0.091(7) 0.015(7) 0.014(7) -0.009(7) -0.004(7) -0.041(7)
0.016(7) 0.078(11) 0.019(10) -0.003(10) -0.006(10) -0.018(10) -0.010(10)
0.016(10) -0.012(10) -0.012(10) 0.988193 1 1 1 1 1
O(2) 6.086(13) 0 0.008(7) 0.004(6) -0.064(7) -0.017(7) 0.010(7) 0.008(7)
-0.062(7) 0.021(7) 0.008(6) 0.005(6) -0.008(6) 0.024(6) -0.008(6) 0.009(6)
0.017(6) 0 0 0 0 0 0 0 0 0 0.992507 1.01878 1.01878 1.01878 1.01878 1.01878
O(3) 6.077(14) 0 0.069(7) 0.011(7) -0.065(7) -0.018(8) 0.005(8) 0.000(7)
-0.103(7) -0.032(8) 0.011(6) -0.037(6) -0.006(6) 0.047(6) -0.001(6) 0.030(6)
0.026(6) 0 0 0 0 0 0 0 0 0 0.992507 1.01878 1.01878 1.01878 1.01878 1.01878
N(125) 4.98(2) 0 0.003(8) 0.017(9) -0.010(8) -0.104(8) 0.014(8) -0.013(8)
-0.007(8) 0.022(8) -0.022(9) 0.018(8) 0.017(8) 0.004(8) 0.007(8) 0.170(8)
0.024(8) 0 0 0 0 0 0 0 0 0 0.992876 0.957786 0.957786 0.957786 0.957786
0.957786
C(121) 4.01(3) 0 0.020(11) 0.002(11) -0.014(10) -0.175(11) -0.044(10) -0.020(9)
-0.009(10) -0.012(10) -0.024(11) 0.001(11) 0.036(11) -0.001(11) 0.021(11)
0.218(11) -0.007(12) 0 0 0 0 0 0 0 0 0 0.989342 0.974437 0.974437 0.974437
0.974437 0.974437
C(122) 4.05(3) 0 0.031(11) 0.015(10) -0.019(10) -0.208(10) 0.002(9) 0.018(9)
0.005(10) 0.004(10) 0.009(11) 0.008(11) 0.018(10) -0.029(11) -0.014(11)
0.258(10) 0.012(11) 0 0 0 0 0 0 0 0 0 0.989342 0.974437 0.974437 0.974437
0.974437 0.974437
C(123) 4.05(3) 0 0.027(10) -0.019(10) 0.010(9) -0.178(10) 0.007(9) -0.009(9)
0.006(9) 0.006(10) 0.009(11) 0.014(10) 0.013(10) -0.017(10) -0.001(10)
0.242(11) -0.018(11) 0 0 0 0 0 0 0 0 0 0.989342 0.974437 0.974437 0.974437
0.974437 0.974437
C(124) 4.00(2) 0 -0.039(10) 0.034(10) -0.008(9) -0.193(9) 0.001(9) 0.020(9)
-0.032(9) -0.013(9) 0.006(11) -0.008(10) 0.040(10) -0.011(10) 0.006(10)
0.275(10) 0.012(11) 0 0 0 0 0 0 0 0 0 0.989342 0.974437 0.974437 0.974437
0.974437 0.974437
C(126) 4.06(3) 0 0.055(11) -0.017(10) -0.002(11) -0.195(10) 0.014(9) -0.008(9)
0.041(10) 0.018(10) 0.014(12) 0.033(11) 0.017(10) 0.006(11) -0.007(11)
0.291(11) -0.014(11) 0 0 0 0 0 0 0 0 0 0.989342 0.974437 0.974437 0.974437
0.974437 0.974437
C(23) 4.25(4) 0 -0.032(11) 0.016(10) 0.055(11) -0.011(10) -0.025(10) -0.019(10)
-0.032(9) 0.046(9) 0.168(13) 0.052(11) 0.000(11) 0.059(11) 0.051(11) -0.017(11)
-0.212(11) 0 0 0 0 0 0 0 0 0 0.983019 0.98967 0.98967 0.98967 0.98967 0.98967
C(24) 4.18(4) 0 0.052(10) 0.016(10) 0.022(9) 0.017(10) -0.020(9) -0.017(9)
0.013(9) -0.001(9) 0.208(12) 0.033(10) 0.038(11) -0.010(10) -0.038(10)
0.014(10) -0.175(10) 0 0 0 0 0 0 0 0 0 0.983019 0.98967 0.98967 0.98967 0.98967
0.98967
C(111) 4.15(3) 0 0.054(10) -0.084(10) -0.015(9) -0.060(9) -0.005(9) -0.003(8)
0.033(9) 0.082(9) -0.007(10) 0.022(9) -0.039(9) -0.008(10) 0.027(10) 0.206(10)
-0.018(11) 0 0 0 0 0 0 0 0 0 0.987912 0.976492 0.976492 0.976492 0.976492
0.976492
C(112) 4.14(2) 0 -0.028(9) -0.032(10) -0.020(9) -0.238(9) 0.012(9) 0.003(9)
-0.075(9) 0.030(9) 0.006(10) 0.005(9) 0.027(9) 0.002(10) -0.010(10) 0.303(10)
0.046(11) 0 0 0 0 0 0 0 0 0 0.987912 0.976492 0.976492 0.976492 0.976492
0.976492
C(113) 4.13(2) 0 0.068(9) -0.030(10) 0.013(9) -0.255(9) 0.013(9) 0.009(9)
0.069(9) 0.023(9) -0.021(10) -0.009(9) -0.008(9) 0.004(10) 0.002(10) 0.326(10)
-0.014(11) 0 0 0 0 0 0 0 0 0 0.987912 0.976492 0.976492 0.976492 0.976492
0.976492
H(121) 0.831(10) 0 0.020(7) 0.013(6) 0.151(8) 0.065(10) 0 0 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 1.188382 1.188382 1.188382 1.188382 1.188382 1.188382
H(122) 0.831(10) 0 0.020(7) 0.013(6) 0.151(8) 0.065(10) 0 0 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 1.188382 1.188382 1.188382 1.188382 1.188382 1.188382
H(125) 0.706(15) 0 0.007(10) -0.003(11) 0.095(12) 0.165(17) 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0 0 1.188382 1.188382 1.188382 1.188382 1.188382 1.188382
H(126) 0.831(10) 0 0.020(7) 0.013(6) 0.151(8) 0.065(10) 0 0 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 1.188382 1.188382 1.188382 1.188382 1.188382 1.188382
H(23A) 0.862(12) 0 0.015(8) -0.048(7) 0.096(8) 0.022(10) 0 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0 1.166859 1.166859 1.166859 1.166859 1.166859 1.166859
H(23B) 0.862(12) 0 0.015(8) -0.048(7) 0.096(8) 0.022(10) 0 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0 1.166859 1.166859 1.166859 1.166859 1.166859 1.166859
H(23C) 0.862(12) 0 0.015(8) -0.048(7) 0.096(8) 0.022(10) 0 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0 1.166859 1.166859 1.166859 1.166859 1.166859 1.166859
H(24A) 0.877(11) 0 0.017(7) -0.031(7) 0.098(8) 0.038(11) 0 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0 1.166859 1.166859 1.166859 1.166859 1.166859 1.166859
H(24B) 0.877(11) 0 0.017(7) -0.031(7) 0.098(8) 0.038(11) 0 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0 1.166859 1.166859 1.166859 1.166859 1.166859 1.166859
H(24C) 0.877(11) 0 0.017(7) -0.031(7) 0.098(8) 0.038(11) 0 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0 1.166859 1.166859 1.166859 1.166859 1.166859 1.166859

loop_
_atom_local_axes_atom_label
_atom_local_axes_atom0
_atom_local_axes_ax1
_atom_local_axes_atom1
_atom_local_axes_atom2
_atom_local_axes_ax2
CL(1) C(111) Z CL(1) C(112) Y
O(2) C(112) Z O(2) H(125) Y
O(3) C(113) Z O(3) H(125) Y
N(125) C(126) X N(125) C(124) Y
C(121) C(122) X C(121) C(126) Y
C(122) C(121) X C(122) C(123) Y
C(123) C(122) X C(123) C(124) Y
C(124) N(125) X C(124) C(123) Y
C(126) C(121) X C(126) N(125) Y
C(23) H(23C) Z C(23) H(23A) Y
C(24) H(24B) Z C(24) H(24A) Y
C(111) C(112) X C(111) CL(1) Y
C(112) C(113) X C(112) C(111) Y
C(113) O(3) X C(113) C(112) Y
H(121) C(121) Z H(121) C(126) Y
H(122) C(122) Z H(122) C(123) Y
H(125) N(125) Z H(125) O(3) Y
H(126) C(126) Z H(126) N(125) Y
H(23A) C(23) Z H(23A) H(23C) Y
H(23B) C(23) Z H(23B) H(23C) Y
H(23C) C(23) Z H(23C) H(23B) Y
H(24A) C(24) Z H(24A) H(24C) Y
H(24B) C(24) Z H(24B) H(24A) Y
H(24C) C(24) Z H(24C) H(24A) Y


#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
CL(1) C(111) 1.74388(17) 1_555 1_555 yes
O(2) C(112) 1.2588(3) 1_555 1_555 yes
O(3) C(113) 1.2384(3) 1_555 1_555 yes
N(125) C(124) 1.3465(3) 1_555 1_555 yes
N(125) C(126) 1.3492(3) 1_555 1_555 yes
N(125) H(125) 1.03300(19) 1_555 1_555 yes
C(121) C(122) 1.4010(3) 1_555 1_555 yes
C(121) C(126) 1.3823(3) 1_555 1_555 yes
C(121) H(121) 1.0830(2) 1_555 1_555 yes
C(122) C(123) 1.3980(3) 1_555 1_555 yes
C(122) H(122) 1.0830(2) 1_555 1_555 yes
C(123) C(124) 1.4040(3) 1_555 1_555 yes
C(123) C(23) 1.5043(3) 1_555 1_555 yes
C(124) C(24) 1.4953(3) 1_555 1_555 yes
C(126) H(126) 1.0830(2) 1_555 1_555 yes
C(23) H(23A) 1.0590(3) 1_555 1_555 yes
C(23) H(23B) 1.0590(3) 1_555 1_555 yes
C(23) H(23C) 1.0590(3) 1_555 1_555 yes
C(24) H(24A) 1.0590(2) 1_555 1_555 yes
C(24) H(24B) 1.0590(2) 1_555 1_555 yes
C(24) H(24C) 1.0590(2) 1_555 1_555 yes
C(111) C(112) 1.3960(2) 1_555 1_555 yes
C(111) C(113) 1.4208(2) 1_555 2_675 yes

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C(124) N(125) C(126) 123.261(19) 1_555 1_555 1_555 yes
C(124) N(125) H(125) 118.192(18) 1_555 1_555 1_555 yes
C(126) N(125) H(125) 118.541(19) 1_555 1_555 1_555 yes
C(122) C(121) C(126) 118.157(18) 1_555 1_555 1_555 yes
C(122) C(121) H(121) 122.34(2) 1_555 1_555 1_555 yes
C(126) C(121) H(121) 119.50(2) 1_555 1_555 1_555 yes
C(121) C(122) C(123) 121.111(19) 1_555 1_555 1_555 yes
C(121) C(122) H(122) 120.138(19) 1_555 1_555 1_555 yes
C(123) C(122) H(122) 118.72(2) 1_555 1_555 1_555 yes
C(122) C(123) C(124) 118.033(18) 1_555 1_555 1_555 yes
C(122) C(123) C(23) 121.940(19) 1_555 1_555 1_555 yes
C(124) C(123) C(23) 120.021(18) 1_555 1_555 1_555 yes
N(125) C(124) C(123) 119.322(17) 1_555 1_555 1_555 yes
N(125) C(124) C(24) 117.530(18) 1_555 1_555 1_555 yes
C(123) C(124) C(24) 123.147(18) 1_555 1_555 1_555 yes
N(125) C(126) C(121) 120.112(19) 1_555 1_555 1_555 yes
N(125) C(126) H(126) 114.672(19) 1_555 1_555 1_555 yes
C(121) C(126) H(126) 125.149(19) 1_555 1_555 1_555 yes
C(123) C(23) H(23A) 113.06(2) 1_555 1_555 1_555 yes
C(123) C(23) H(23B) 111.68(2) 1_555 1_555 1_555 yes
C(123) C(23) H(23C) 112.91(2) 1_555 1_555 1_555 yes
H(23A) C(23) H(23B) 107.59(3) 1_555 1_555 1_555 yes
H(23A) C(23) H(23C) 107.52(2) 1_555 1_555 1_555 yes
H(23B) C(23) H(23C) 103.48(2) 1_555 1_555 1_555 yes
C(124) C(24) H(24A) 111.544(19) 1_555 1_555 1_555 yes
C(124) C(24) H(24B) 109.092(18) 1_555 1_555 1_555 yes
C(124) C(24) H(24C) 107.751(19) 1_555 1_555 1_555 yes
H(24A) C(24) H(24B) 111.44(2) 1_555 1_555 1_555 yes
H(24A) C(24) H(24C) 106.03(2) 1_555 1_555 1_555 yes
H(24B) C(24) H(24C) 110.90(2) 1_555 1_555 1_555 yes
CL(1) C(111) C(112) 118.744(13) 1_555 1_555 1_555 yes
CL(1) C(111) C(113) 117.886(13) 1_555 1_555 2_675 yes
C(112) C(111) C(113) 123.229(16) 1_555 1_555 2_675 yes
O(2) C(112) C(111) 124.980(18) 1_555 1_555 1_555 yes
O(3) C(113) C(111) 124.834(19) 1_555 1_555 2_675 yes

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
C(124) N(125) C(126) C(121) 0.19(2) 1_555 1_555 1_555 1_555 yes
C(126) N(125) C(124) C(123) -0.62(2) 1_555 1_555 1_555 1_555 yes
C(126) N(125) C(124) C(24) 179.00(3) 1_555 1_555 1_555 1_555 yes
C(124) N(125) C(126) H(126) 177.37(3) 1_555 1_555 1_555 1_555 yes
H(125) N(125) C(124) C(123) 178.48(3) 1_555 1_555 1_555 1_555 yes
H(125) N(125) C(124) C(24) -1.891(18) 1_555 1_555 1_555 1_555 yes
H(125) N(125) C(126) C(121) -178.92(3) 1_555 1_555 1_555 1_555 yes
H(125) N(125) C(126) H(126) -1.735(18) 1_555 1_555 1_555 1_555 yes
C(122) C(121) C(126) N(125) 0.05(2) 1_555 1_555 1_555 1_555 yes
C(126) C(121) C(122) C(123) 0.17(2) 1_555 1_555 1_555 1_555 yes
C(126) C(121) C(122) H(122) -177.87(3) 1_555 1_555 1_555 1_555 yes
C(122) C(121) C(126) H(126) -176.82(3) 1_555 1_555 1_555 1_555 yes
H(121) C(121) C(122) C(123) 179.54(3) 1_555 1_555 1_555 1_555 yes
H(121) C(121) C(122) H(122) 1.505(19) 1_555 1_555 1_555 1_555 yes
H(121) C(121) C(126) N(125) -179.35(3) 1_555 1_555 1_555 1_555 yes
H(121) C(121) C(126) H(126) 3.788(19) 1_555 1_555 1_555 1_555 yes
C(121) C(122) C(123) C(124) -0.585(19) 1_555 1_555 1_555 1_555 yes
C(121) C(122) C(123) C(23) 178.43(3) 1_555 1_555 1_555 1_555 yes
H(122) C(122) C(123) C(124) 177.48(3) 1_555 1_555 1_555 1_555 yes
H(122) C(122) C(123) C(23) -3.51(2) 1_555 1_555 1_555 1_555 yes
C(122) C(123) C(124) N(125) 0.799(19) 1_555 1_555 1_555 1_555 yes
C(122) C(123) C(124) C(24) -178.80(3) 1_555 1_555 1_555 1_555 yes
C(122) C(123) C(23) H(23A) -123.56(3) 1_555 1_555 1_555 1_555 yes
C(122) C(123) C(23) H(23B) -2.04(2) 1_555 1_555 1_555 1_555 yes
C(122) C(123) C(23) H(23C) 114.09(3) 1_555 1_555 1_555 1_555 yes
C(23) C(123) C(124) N(125) -178.23(3) 1_555 1_555 1_555 1_555 yes
C(23) C(123) C(124) C(24) 2.17(2) 1_555 1_555 1_555 1_555 yes
C(124) C(123) C(23) H(23A) 55.44(2) 1_555 1_555 1_555 1_555 yes
C(124) C(123) C(23) H(23B) 176.96(3) 1_555 1_555 1_555 1_555 yes
C(124) C(123) C(23) H(23C) -66.92(2) 1_555 1_555 1_555 1_555 yes
N(125) C(124) C(24) H(24A) 3.593(18) 1_555 1_555 1_555 1_555 yes
N(125) C(124) C(24) H(24B) 127.13(3) 1_555 1_555 1_555 1_555 yes
N(125) C(124) C(24) H(24C) -112.39(2) 1_555 1_555 1_555 1_555 yes
C(123) C(124) C(24) H(24A) -176.80(3) 1_555 1_555 1_555 1_555 yes
C(123) C(124) C(24) H(24B) -53.26(2) 1_555 1_555 1_555 1_555 yes
C(123) C(124) C(24) H(24C) 67.21(2) 1_555 1_555 1_555 1_555 yes
CL(1) C(111) C(112) O(2) -1.397(18) 1_555 1_555 1_555 1_555 yes
C(113) C(111) C(112) O(2) -176.99(3) 2_675 1_555 1_555 1_555 yes
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_(2,4)_shelx
_database_code_depnum_ccdc_archive 'CCDC 1478075'
_audit_update_record             
;
2016-05-04 deposited with the CCDC.
2016-06-13 downloaded from the CCDC.
;

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         
;
C6 H Cl2 O4, C7 H10 N 
;
_chemical_formula_sum            'C13 H11 Cl2 N O4'
_chemical_formula_weight         316.13
_chemical_compound_source        commercial

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_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_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.0687(2)
_cell_length_b                   11.2561(4)
_cell_length_c                   11.6281(3)
_cell_angle_alpha                96.274(2)
_cell_angle_beta                 91.960(2)
_cell_angle_gamma                90.6090(10)
_cell_volume                     659.00(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    13978
_cell_measurement_theta_min      2
_cell_measurement_theta_max      50.44
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.17
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             324

_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.504
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5458
_exptl_absorpt_correction_T_max  0.7495
_exptl_absorpt_process_details   'SADABS, Bruker(2001)'

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_ub_11      0.344261E-1
_diffrn_orient_matrix_ub_21      -0.1902439
_diffrn_orient_matrix_ub_31      -0.400009E-1
_diffrn_orient_matrix_ub_12      -0.777945E-1
_diffrn_orient_matrix_ub_22      -0.233391E-1
_diffrn_orient_matrix_ub_32      0.372261E-1
_diffrn_orient_matrix_ub_13      -0.468051E-1
_diffrn_orient_matrix_ub_23      0.36180E-2
_diffrn_orient_matrix_ub_33      -0.727386E-1
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_number            13978
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.39
_diffrn_reflns_theta_max         50.66
_diffrn_reflns_theta_full        50.66
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_reflns_number_total             13978
_reflns_number_gt                12202
_reflns_threshold_expression     >2σ(I)
_diffrn_reflns_reduction_process 
;
 Scaled and merged with Sortav
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0468P)²+0.0233P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         13978
_refine_ls_number_parameters     225
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0247
_refine_ls_wR_factor_ref         0.0786
_refine_ls_wR_factor_gt          0.0763
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.642
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.064

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.644627(15) 0.890467(7) 0.089341(7) 0.01454(2) Uani 1 1 d . . .
Cl2 Cl -0.229718(15) 0.573319(7) 0.295079(7) 0.01559(2) Uani 1 1 d . . .
O2 O 0.27063(5) 0.96807(2) 0.27820(2) 0.01566(4) Uani 1 1 d . . .
O3 O -0.10170(5) 0.83165(2) 0.35964(2) 0.01632(4) Uani 1 1 d . . .
O5 O 0.15853(5) 0.49569(2) 0.11480(2) 0.01525(3) Uani 1 1 d . . .
O6 O 0.49875(6) 0.63389(2) 0.02151(2) 0.01690(4) Uani 1 1 d . . .
N125 N -0.15007(5) 1.10799(2) 0.32324(2) 0.01263(3) Uani 1 1 d . . .
C121 C -0.46891(6) 1.20012(3) 0.44656(3) 0.01451(4) Uani 1 1 d . . .
C122 C -0.53264(6) 1.27732(3) 0.36306(3) 0.01334(4) Uani 1 1 d . . .
C123 C -0.39948(6) 1.26514(3) 0.25929(3) 0.01373(4) Uani 1 1 d . . .
C124 C -0.20357(6) 1.18017(3) 0.24048(2) 0.01250(3) Uani 1 1 d . . .
C126 C -0.27868(6) 1.11498(3) 0.42344(3) 0.01414(4) Uani 1 1 d . . .
C22 C -0.73768(7) 1.37171(3) 0.38502(3) 0.01841(5) Uani 1 1 d . . .
C24 C -0.04685(7) 1.16702(3) 0.13306(3) 0.01659(4) Uani 1 1 d . . .
C111 C 0.40709(5) 0.80629(2) 0.14825(2) 0.01148(3) Uani 1 1 d . . .
C112 C 0.25178(5) 0.86085(2) 0.23545(2) 0.01145(3) Uani 1 1 d . . .
C113 C 0.03609(5) 0.78402(2) 0.28374(2) 0.01171(3) Uani 1 1 d . . .
C114 C 0.00907(5) 0.65851(2) 0.23854(2) 0.01212(3) Uani 1 1 d . . .
C115 C 0.17004(6) 0.61026(2) 0.15532(2) 0.01178(3) Uani 1 1 d . . .
C116 C 0.37411(6) 0.68529(2) 0.10261(2) 0.01169(3) Uani 1 1 d . . .
H121 H -0.5519(18) 1.2025(8) 0.5189(8) 0.027(2) Uiso 1 1 d . . .
H123 H -0.4363(17) 1.3217(7) 0.2020(7) 0.0222(19) Uiso 1 1 d . . .
H125 H -0.008(2) 1.0486(10) 0.3121(9) 0.041(3) Uiso 1 1 d . . .
H126 H -0.2372(17) 1.0558(8) 0.4730(8) 0.0221(18) Uiso 1 1 d . . .
H22A H -0.825(2) 1.3907(9) 0.3107(9) 0.036(2) Uiso 1 1 d . . .
H22B H -0.655(2) 1.4458(10) 0.4239(10) 0.043(3) Uiso 1 1 d . . .
H22C H -0.8847(18) 1.3406(8) 0.4394(8) 0.029(2) Uiso 1 1 d . . .
H24A H 0.1011(18) 1.1133(8) 0.1398(8) 0.029(2) Uiso 1 1 d . . .
H24B H -0.1630(19) 1.1319(9) 0.0634(9) 0.034(2) Uiso 1 1 d . . .
H24C H 0.0126(19) 1.2447(9) 0.1177(9) 0.037(3) Uiso 1 1 d . . .
H5 H 0.285(2) 0.4835(10) 0.0612(10) 0.050(3) Uiso 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 C111 1.7293(3) . ?
Cl2 C114 1.7275(3) . ?
O2 C112 1.2554(3) . ?
O3 C113 1.2250(4) . ?
O5 C115 1.3238(4) . ?
O5 H5 0.910(12) . ?
O6 C116 1.2460(4) . ?
N125 C124 1.3481(4) . ?
N125 C126 1.3497(4) . ?
N125 H125 0.991(11) . ?
C121 C126 1.3789(4) . ?
C121 C122 1.4040(4) . ?
C121 H121 0.951(9) . ?
C122 C123 1.3971(4) . ?
C122 C22 1.5022(4) . ?
C123 C124 1.3921(4) . ?
C123 H123 0.984(8) . ?
C124 C24 1.4977(4) . ?
C126 H126 0.948(9) . ?
C22 H22A 1.003(11) . ?
C22 H22B 0.986(11) . ?
C22 H22C 1.074(10) . ?
C24 H24A 0.975(9) . ?
C24 H24B 1.026(10) . ?
C24 H24C 0.959(10) . ?
C111 C112 1.3978(4) . ?
C111 C116 1.4127(4) . ?
C112 C113 1.5448(4) . ?
C113 C114 1.4559(4) . ?
C114 C115 1.3586(4) . ?
C115 C116 1.5155(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
C115 O5 H5 107.2(7) . . ?
C124 N125 C126 122.61(3) . . ?
C124 N125 H125 119.5(7) . . ?
C126 N125 H125 117.8(6) . . ?
C126 C121 C122 119.13(3) . . ?
C126 C121 H121 117.5(5) . . ?
C122 C121 H121 123.4(5) . . ?
C123 C122 C121 118.53(3) . . ?
C123 C122 C22 120.63(3) . . ?
C121 C122 C22 120.84(3) . . ?
C124 C123 C122 120.60(3) . . ?
C124 C123 H123 120.2(5) . . ?
C122 C123 H123 119.0(5) . . ?
N125 C124 C123 118.58(3) . . ?
N125 C124 C24 118.68(3) . . ?
C123 C124 C24 122.73(3) . . ?
N125 C126 C121 120.51(3) . . ?
N125 C126 H126 116.1(5) . . ?
C121 C126 H126 123.3(5) . . ?
C122 C22 H22A 111.1(6) . . ?
C122 C22 H22B 110.1(6) . . ?
H22A C22 H22B 108.1(9) . . ?
C122 C22 H22C 109.3(5) . . ?
H22A C22 H22C 109.0(8) . . ?
H22B C22 H22C 109.1(8) . . ?
C124 C24 H24A 111.8(5) . . ?
C124 C24 H24B 110.4(6) . . ?
H24A C24 H24B 107.2(8) . . ?
C124 C24 H24C 108.7(6) . . ?
H24A C24 H24C 111.2(8) . . ?
H24B C24 H24C 107.6(8) . . ?
C112 C111 C116 122.99(2) . . ?
C112 C111 Cl1 119.21(2) . . ?
C116 C111 Cl1 117.77(2) . . ?
O2 C112 C111 125.64(3) . . ?
O2 C112 C113 116.47(2) . . ?
C111 C112 C113 117.89(2) . . ?
O3 C113 C114 123.20(3) . . ?
O3 C113 C112 118.13(3) . . ?
C114 C113 C112 118.66(2) . . ?
C115 C114 C113 120.55(3) . . ?
C115 C114 Cl2 121.39(2) . . ?
C113 C114 Cl2 118.06(2) . . ?
O5 C115 C114 122.51(3) . . ?
O5 C115 C116 115.81(2) . . ?
C114 C115 C116 121.68(2) . . ?
O6 C116 C111 125.54(3) . . ?
O6 C116 C115 116.36(2) . . ?
C111 C116 C115 118.10(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
C126 C121 C122 C123 -0.22(5) . . . . ?
C126 C121 C122 C22 -179.68(3) . . . . ?
C121 C122 C123 C124 -1.52(4) . . . . ?
C22 C122 C123 C124 177.95(3) . . . . ?
C126 N125 C124 C123 -0.06(4) . . . . ?
C126 N125 C124 C24 178.94(3) . . . . ?
C122 C123 C124 N125 1.68(4) . . . . ?
C122 C123 C124 C24 -177.27(3) . . . . ?
C124 N125 C126 C121 -1.71(5) . . . . ?
C122 C121 C126 N125 1.82(5) . . . . ?
C116 C111 C112 O2 -179.19(3) . . . . ?
Cl1 C111 C112 O2 -1.26(4) . . . . ?
C116 C111 C112 C113 0.35(4) . . . . ?
Cl1 C111 C112 C113 178.284(19) . . . . ?
O2 C112 C113 O3 0.06(4) . . . . ?
C111 C112 C113 O3 -179.53(3) . . . . ?
O2 C112 C113 C114 -178.93(3) . . . . ?
C111 C112 C113 C114 1.48(4) . . . . ?
O3 C113 C114 C115 -179.13(3) . . . . ?
C112 C113 C114 C115 -0.20(4) . . . . ?
O3 C113 C114 Cl2 0.08(4) . . . . ?
C112 C113 C114 Cl2 179.015(19) . . . . ?
C113 C114 C115 O5 177.53(3) . . . . ?
Cl2 C114 C115 O5 -1.66(4) . . . . ?
C113 C114 C115 C116 -2.78(4) . . . . ?
Cl2 C114 C115 C116 178.03(2) . . . . ?
C112 C111 C116 O6 176.55(3) . . . . ?
Cl1 C111 C116 O6 -1.41(4) . . . . ?
C112 C111 C116 C115 -3.21(4) . . . . ?
Cl1 C111 C116 C115 178.84(2) . . . . ?
O5 C115 C116 O6 4.47(4) . . . . ?
C114 C115 C116 O6 -175.24(3) . . . . ?
O5 C115 C116 C111 -175.75(3) . . . . ?
C114 C115 C116 C111 4.54(4) . . . . ?

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

data_1_(2,4)_xd
_database_code_depnum_ccdc_archive 'CCDC 1478076'
_audit_update_record             
;
2016-05-04 deposited with the CCDC.
2016-06-13 downloaded from the CCDC.
;

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         
;
C6 H Cl2 O4, C7 H10 N 
;
_chemical_formula_sum            'C13 H11 Cl2 N O4'
_chemical_formula_weight         316.13
_chemical_compound_source        commercial

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#
_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                   5.0687(2)
_cell_length_b                   11.2561(4)
_cell_length_c                   11.6281(3)
_cell_angle_alpha                96.274(2)
_cell_angle_beta                 91.960(2)
_cell_angle_gamma                90.6090(10)
_cell_volume                     659.00(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    13978
_cell_measurement_theta_min      2
_cell_measurement_theta_max      50.44
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.17
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             324

_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.504
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5458
_exptl_absorpt_correction_T_max  0.7495
_exptl_absorpt_process_details   'SADABS, Bruker(2001)'

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      0.344261E-1
_diffrn_orient_matrix_UB_21      -0.1902439
_diffrn_orient_matrix_UB_31      -0.400009E-1
_diffrn_orient_matrix_UB_12      -0.777945E-1
_diffrn_orient_matrix_UB_22      -0.233391E-1
_diffrn_orient_matrix_UB_32      0.372261E-1
_diffrn_orient_matrix_UB_13      -0.468051E-1
_diffrn_orient_matrix_UB_23      0.36180E-2
_diffrn_orient_matrix_UB_33      -0.727386E-1
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_number            13978
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.39
_diffrn_reflns_theta_max         50.66
_diffrn_reflns_theta_full        50.66
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_reflns_number_total             13978
_reflns_number_gt                12202
_reflns_threshold_expression     >2σ(I)
_diffrn_reflns_reduction_process 
;
 Scaled and merged with Sortav
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
        ?
;
_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
        calc w1 = 1/[s²(Fo)]
;
_refine_ls_extinction_method     'Becker-Coppens type 1 Lorentzian isotropic'
_refine_ls_extinction_expression 
;
        Becker, P.J. & Coppens, P. (1974) Acta Cryst., A30, 129-153.
;
_refine_ls_extinction_coef       0.028(8)
_refine_ls_number_reflns         12502
_refine_ls_number_parameters     543
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.022
_refine_ls_R_factor_gt           0.016
_refine_ls_wR_factor_ref         0.02
_refine_ls_goodness_of_fit_ref   1.204
_refine_ls_shift/su_max          0.00005
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.035

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, 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_symmetry_multiplicity
Cl(1) Cl 0.644613(10) 0.890468(4) 0.089352(4) 0.014 Uani 1 2
Cl(2) Cl -0.229714(10) 0.573322(5) 0.295077(5) 0.016 Uani 1 2
O(2) O 0.27070(4) 0.967959(19) 0.27826(2) 0.016 Uani 1 2
O(3) O -0.10167(5) 0.83173(2) 0.35957(2) 0.016 Uani 1 2
O(5) O 0.15885(5) 0.495754(18) 0.11477(2) 0.015 Uani 1 2
O(6) O 0.49860(6) 0.63396(2) 0.02151(2) 0.017 Uani 1 2
N(125) N -0.15005(4) 1.107962(17) 0.323233(16) 0.012 Uani 1 2
C(121) C -0.46892(4) 1.20011(2) 0.446553(18) 0.014 Uani 1 2
C(122) C -0.53273(4) 1.277393(18) 0.363017(18) 0.013 Uani 1 2
C(123) C -0.39948(4) 1.265148(19) 0.259249(18) 0.014 Uani 1 2
C(124) C -0.20351(4) 1.180166(18) 0.240471(17) 0.012 Uani 1 2
C(126) C -0.27863(4) 1.114913(19) 0.423401(18) 0.014 Uani 1 2
C(22) C -0.73754(5) 1.37176(2) 0.38496(2) 0.018 Uani 1 2
C(24) C -0.04693(5) 1.16700(2) 0.13312(2) 0.016 Uani 1 2
C(111) C 0.40717(4) 0.806297(16) 0.148231(16) 0.011 Uani 1 2
C(112) C 0.25177(4) 0.860874(16) 0.235467(16) 0.011 Uani 1 2
C(113) C 0.03601(4) 0.783969(17) 0.283714(16) 0.012 Uani 1 2
C(114) C 0.00897(4) 0.658518(17) 0.238583(17) 0.012 Uani 1 2
C(115) C 0.16996(4) 0.610173(16) 0.155272(16) 0.012 Uani 1 2
C(116) C 0.37412(4) 0.685337(16) 0.102610(16) 0.012 Uani 1 2
H(121) H -0.563897 1.20287 0.529386 0.031 Uani 1 2
H(123) H -0.440376 1.327916 0.195714 0.032 Uani 1 2
H(125) H 0.002559 1.044209 0.311266 0.025 Uani 1 2
H(126) H -0.231153 1.047205 0.480281 0.033 Uani 1 2
H(22A) H -0.832426 1.392281 0.304571 0.051 Uani 1 2
H(22B) H -0.647237 1.452977 0.427713 0.055 Uani 1 2
H(22C) H -0.886522 1.340236 0.440061 0.049 Uani 1 2
H(24A) H 0.117841 1.107249 0.140609 0.045 Uani 1 2
H(24B) H -0.169827 1.129828 0.059298 0.044 Uani 1 2
H(24C) H 0.02054 1.25512 0.115625 0.046 Uani 1 2
H(5) H 0.296271 0.482369 0.056322 0.029 Uani 1 2



#----------------------------------------------------------------------------#
#                   MULTIPOLE PARAMETERS                                     #
#----------------------------------------------------------------------------#

loop_
_atom_rho_multipole_atom_label
_atom_rho_multipole_coeff_Pv
_atom_rho_multipole_coeff_P00
_atom_rho_multipole_coeff_P11
_atom_rho_multipole_coeff_P1-1
_atom_rho_multipole_coeff_P10
_atom_rho_multipole_coeff_P20
_atom_rho_multipole_coeff_P21
_atom_rho_multipole_coeff_P2-1
_atom_rho_multipole_coeff_P22
_atom_rho_multipole_coeff_P2-2
_atom_rho_multipole_coeff_P30
_atom_rho_multipole_coeff_P31
_atom_rho_multipole_coeff_P3-1
_atom_rho_multipole_coeff_P32
_atom_rho_multipole_coeff_P3-2
_atom_rho_multipole_coeff_P33
_atom_rho_multipole_coeff_P3-3
_atom_rho_multipole_coeff_P40
_atom_rho_multipole_coeff_P41
_atom_rho_multipole_coeff_P4-1
_atom_rho_multipole_coeff_P42
_atom_rho_multipole_coeff_P4-2
_atom_rho_multipole_coeff_P43
_atom_rho_multipole_coeff_P4-3
_atom_rho_multipole_coeff_P44
_atom_rho_multipole_coeff_P4-4
_atom_rho_multipole_kappa
_atom_rho_multipole_kappa_prime0
_atom_rho_multipole_kappa_prime1
_atom_rho_multipole_kappa_prime2
_atom_rho_multipole_kappa_prime3
_atom_rho_multipole_kappa_prime4
Cl(1) 7.25(2) 0 0.075(9) 0.021(9) -0.035(9) -0.114(13) 0.003(11) -0.021(12)
-0.011(12) 0.027(11) 0.053(8) -0.018(7) -0.021(8) -0.001(7) 0.002(8) -0.008(7)
0.012(7) 0.067(11) -0.027(10) -0.005(10) 0.003(10) -0.015(10) -0.012(10)
-0.009(10) -0.005(9) 0.020(10) 0.990085 1 1 1 1 1
Cl(2) 7.20(2) 0 0.023(9) 0.026(9) -0.022(9) -0.124(13) 0.003(12) 0.031(12)
-0.014(11) -0.020(11) 0.063(8) 0.000(7) -0.014(8) 0.000(7) -0.046(7) 0.075(7)
-0.025(7) 0.061(11) -0.021(10) 0.006(10) -0.012(11) 0.013(11) -0.013(10)
0.007(10) -0.018(10) -0.016(10) 0.990085 1 1 1 1 1
O(2) 6.074(13) 0 0.025(7) 0.024(7) -0.069(7) -0.026(8) 0.003(7) -0.003(7)
-0.083(7) -0.008(7) 0.033(6) -0.014(6) -0.006(6) 0.025(6) 0.007(6) -0.002(6)
0.019(6) 0 0 0 0 0 0 0 0 0 0.994251 1.006852 1.006852 1.006852 1.006852
1.006852
O(3) 6.075(14) 0 -0.022(7) -0.027(7) -0.052(7) 0.008(8) 0.009(7) 0.011(7)
-0.103(8) -0.070(8) 0.016(7) 0.010(6) 0.013(6) 0.018(6) 0.013(7) 0.027(7)
-0.014(7) 0 0 0 0 0 0 0 0 0 0.994251 1.006852 1.006852 1.006852 1.006852
1.006852
O(5) 5.971(16) 0 0.006(7) -0.067(7) -0.037(8) 0.011(8) -0.005(7) 0.035(7)
0.025(7) -0.002(7) 0.088(7) 0.009(6) -0.037(6) 0.019(6) 0.002(6) -0.008(6)
-0.009(6) 0 0 0 0 0 0 0 0 0 0.996266 1.020751 1.020751 1.020751 1.020751
1.020751
O(6) 6.123(14) 0 -0.004(8) 0.017(7) -0.053(7) -0.002(8) 0.001(8) 0.015(7)
-0.090(8) 0.013(8) 0.000(7) -0.002(7) -0.012(6) 0.012(7) -0.003(7) -0.027(7)
0.012(7) 0 0 0 0 0 0 0 0 0 0.994251 1.006852 1.006852 1.006852 1.006852
1.006852
N(125) 4.969(19) 0 -0.019(8) -0.012(9) 0.000(7) -0.111(8) -0.009(7) 0.015(7)
-0.005(8) 0.003(8) 0.004(8) 0.007(8) 0.012(8) -0.006(8) 0.001(8) 0.207(8)
0.008(9) 0 0 0 0 0 0 0 0 0 0.997002 0.946391 0.946391 0.946391 0.946391
0.946391
C(121) 4.22(2) 0 -0.033(11) -0.041(10) 0.000(9) -0.195(9) 0.009(9) 0.011(8)
-0.044(10) 0.056(10) -0.007(11) 0.022(11) 0.030(10) 0.011(11) -0.004(11)
0.261(11) -0.001(12) 0 0 0 0 0 0 0 0 0 0.991983 0.974672 0.974672 0.974672
0.974672 0.974672
C(122) 4.04(2) 0 -0.008(10) 0.031(10) 0.006(9) -0.231(9) 0.011(9) 0.001(9)
0.001(10) 0.001(10) -0.005(11) 0.032(10) 0.023(10) 0.001(11) 0.007(11)
0.261(11) 0.019(12) 0 0 0 0 0 0 0 0 0 0.991983 0.974672 0.974672 0.974672
0.974672 0.974672
C(123) 4.17(3) 0 0.015(11) -0.032(11) 0.003(10) -0.191(10) 0.005(9) 0.027(9)
0.009(10) 0.024(9) 0.015(11) 0.021(10) 0.053(10) -0.004(10) -0.011(11)
0.290(11) -0.038(11) 0 0 0 0 0 0 0 0 0 0.991983 0.974672 0.974672 0.974672
0.974672 0.974672
C(124) 4.01(2) 0 -0.036(10) 0.030(10) -0.012(9) -0.200(9) -0.006(9) 0.007(8)
-0.051(9) -0.002(10) -0.012(10) 0.011(10) 0.018(9) -0.013(11) 0.008(10)
0.279(11) 0.015(12) 0 0 0 0 0 0 0 0 0 0.991983 0.974672 0.974672 0.974672
0.974672 0.974672
C(126) 4.14(2) 0 0.020(10) -0.050(10) -0.007(9) -0.231(9) 0.008(9) -0.001(9)
0.024(9) 0.053(9) 0.003(11) 0.041(10) 0.034(10) 0.007(10) -0.010(11) 0.293(11)
-0.022(11) 0 0 0 0 0 0 0 0 0 0.991983 0.974672 0.974672 0.974672 0.974672
0.974672
C(22) 3.96(4) 0 -0.029(10) 0.000(10) 0.008(9) -0.014(9) 0.024(9) 0.000(9)
-0.011(9) 0.018(9) 0.176(11) 0.001(10) -0.038(10) -0.025(10) 0.027(10)
-0.026(11) -0.174(11) 0 0 0 0 0 0 0 0 0 0.992607 0.986478 0.986478 0.986478
0.986478 0.986478
C(24) 4.02(4) 0 -0.031(10) 0.012(10) 0.035(9) 0.015(9) -0.001(9) -0.013(9)
-0.036(8) 0.033(9) 0.182(12) -0.028(10) 0.027(10) 0.015(10) 0.012(10)
-0.029(11) -0.179(11) 0 0 0 0 0 0 0 0 0 0.992607 0.986478 0.986478 0.986478
0.986478 0.986478
C(111) 4.09(2) 0 0.049(11) 0.080(10) 0.020(9) -0.072(9) 0.000(9) 0.006(8)
0.028(9) -0.061(9) 0.004(11) 0.006(10) 0.035(10) -0.001(10) 0.019(10) 0.217(11)
0.030(11) 0 0 0 0 0 0 0 0 0 0.991946 0.975576 0.975576 0.975576 0.975576
0.975576
C(112) 4.08(2) 0 -0.063(10) -0.021(10) -0.023(9) -0.250(9) 0.017(9) 0.005(8)
-0.065(10) 0.010(9) 0.007(10) -0.011(10) 0.038(10) 0.003(10) -0.009(10)
0.285(11) 0.021(12) 0 0 0 0 0 0 0 0 0 0.991946 0.975576 0.975576 0.975576
0.975576 0.975576
C(113) 4.12(2) 0 -0.041(10) -0.068(9) -0.024(9) -0.260(9) -0.001(9) 0.002(9)
-0.048(9) 0.055(9) 0.012(11) -0.004(10) -0.011(10) -0.011(10) 0.002(10)
0.314(11) 0.017(12) 0 0 0 0 0 0 0 0 0 0.991946 0.975576 0.975576 0.975576
0.975576 0.975576
C(114) 4.09(2) 0 0.039(10) 0.082(10) 0.000(9) -0.089(9) -0.008(9) 0.016(9)
0.007(9) -0.061(10) -0.012(11) 0.008(10) 0.047(10) -0.012(10) -0.005(10)
0.214(11) 0.030(12) 0 0 0 0 0 0 0 0 0 0.991946 0.975576 0.975576 0.975576
0.975576 0.975576
C(115) 4.10(3) 0 0.002(10) 0.043(10) 0.009(9) -0.203(9) 0.001(9) 0.001(9)
-0.011(10) -0.077(9) -0.009(11) 0.003(10) 0.064(10) 0.013(10) 0.002(10)
0.284(11) 0.062(12) 0 0 0 0 0 0 0 0 0 0.991946 0.975576 0.975576 0.975576
0.975576 0.975576
C(116) 4.10(2) 0 -0.049(10) -0.033(10) -0.012(9) -0.234(9) 0.008(9) -0.020(9)
-0.093(10) 0.011(9) -0.005(11) -0.011(10) 0.003(10) 0.015(10) -0.010(10)
0.302(11) 0.035(12) 0 0 0 0 0 0 0 0 0 0.991946 0.975576 0.975576 0.975576
0.975576 0.975576
H(121) 0.777(9) 0 0.047(6) -0.036(6) 0.078(7) 0.023(9) 0 0 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 1.207123 1.207123 1.207123 1.207123 1.207123 1.207123
H(123) 0.777(9) 0 0.047(6) -0.036(6) 0.078(7) 0.023(9) 0 0 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 1.207123 1.207123 1.207123 1.207123 1.207123 1.207123
H(125) 0.683(13) 0 0.019(9) 0.013(10) 0.120(11) 0.165(15) 0 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0 1.207123 1.207123 1.207123 1.207123 1.207123 1.207123
H(126) 0.777(9) 0 0.047(6) -0.036(6) 0.078(7) 0.023(9) 0 0 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 1.207123 1.207123 1.207123 1.207123 1.207123 1.207123
H(22A) 0.924(11) 0 0.040(7) 0.001(7) 0.149(8) 0.097(11) 0 0 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 1.193775 1.193775 1.193775 1.193775 1.193775 1.193775
H(22B) 0.924(11) 0 0.040(7) 0.001(7) 0.149(8) 0.097(11) 0 0 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 1.193775 1.193775 1.193775 1.193775 1.193775 1.193775
H(22C) 0.924(11) 0 0.040(7) 0.001(7) 0.149(8) 0.097(11) 0 0 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 1.193775 1.193775 1.193775 1.193775 1.193775 1.193775
H(24A) 0.898(11) 0 -0.003(7) 0.021(7) 0.138(8) 0.083(11) 0 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0 1.193775 1.193775 1.193775 1.193775 1.193775 1.193775
H(24B) 0.898(11) 0 -0.003(7) 0.021(7) 0.138(8) 0.083(11) 0 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0 1.193775 1.193775 1.193775 1.193775 1.193775 1.193775
H(24C) 0.898(11) 0 -0.003(7) 0.021(7) 0.138(8) 0.083(11) 0 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0 1.193775 1.193775 1.193775 1.193775 1.193775 1.193775
H(5) 0.724(15) 0 0.002(10) -0.028(10) 0.200(11) 0.138(16) 0 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0 1.208528 1.208528 1.208528 1.208528 1.208528 1.208528

loop_
_atom_local_axes_atom_label
_atom_local_axes_atom0
_atom_local_axes_ax1
_atom_local_axes_atom1
_atom_local_axes_atom2
_atom_local_axes_ax2
CL(1) C(111) Z CL(1) C(116) Y
CL(2) C(114) Z CL(2) C(115) Y
O(2) C(112) Z O(2) C(111) Y
O(3) C(113) Z O(3) H(125) Y
O(5) H(5) Z O(5) C(115) Y
O(6) C(116) Z O(6) H(5) Y
N(125) C(126) X N(125) C(124) Y
C(121) C(122) X C(121) C(126) Y
C(122) C(123) X C(122) C(121) Y
C(123) C(122) X C(123) C(124) Y
C(124) N(125) X C(124) C(123) Y
C(126) C(121) X C(126) N(125) Y
C(22) H(22B) Z C(22) H(22A) Y
C(24) H(24C) Z C(24) H(24A) Y
C(111) C(116) X C(111) C(112) Y
C(112) C(113) X C(112) C(111) Y
C(113) C(112) X C(113) C(114) Y
C(114) C(113) X C(114) C(115) Y
C(115) C(116) X C(115) C(114) Y
C(116) C(115) X C(116) C(111) Y
H(121) C(121) X H(121) C(126) Y
H(123) C(123) Z H(123) C(122) Y
H(125) N(125) Z H(125) O(3) Y
H(126) C(126) Z H(126) N(125) Y
H(22A) C(22) Z H(22A) H(22B) Y
H(22B) C(22) Z H(22B) H(22A) Y
H(22C) C(22) Z H(22C) H(22B) Y
H(24A) C(24) Z H(24A) H(24C) Y
H(24B) C(24) Z H(24B) H(24C) Y
H(24C) C(24) Z H(24C) H(24A) Y
H(5) O(5) Z H(5) C(115) Y


#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
CL(1) C(111) 1.72881(19) 1_555 1_555 yes
CL(2) C(114) 1.72693(19) 1_555 1_555 yes
O(2) C(112) 1.2541(3) 1_555 1_555 yes
O(3) C(113) 1.2249(3) 1_555 1_555 yes
O(5) C(115) 1.3220(3) 1_555 1_555 yes
O(5) H(5) 0.9910(2) 1_555 1_555 yes
O(6) C(116) 1.2454(3) 1_555 1_555 yes
N(125) C(124) 1.3483(3) 1_555 1_555 yes
N(125) C(126) 1.3493(3) 1_555 1_555 yes
N(125) H(125) 1.06300(19) 1_555 1_555 yes
C(121) C(122) 1.4050(3) 1_555 1_555 yes
C(121) C(126) 1.3796(3) 1_555 1_555 yes
C(121) H(121) 1.0890(2) 1_555 1_555 yes
C(122) C(123) 1.3973(3) 1_555 1_555 yes
C(122) C(22) 1.5012(3) 1_555 1_555 yes
C(123) C(124) 1.3924(3) 1_555 1_555 yes
C(123) H(123) 1.0930(2) 1_555 1_555 yes
C(124) C(24) 1.4967(3) 1_555 1_555 yes
C(126) H(126) 1.0860(2) 1_555 1_555 yes
C(22) H(22A) 1.0850(3) 1_555 1_555 yes
C(22) H(22B) 1.0810(3) 1_555 1_555 yes
C(22) H(22C) 1.0880(3) 1_555 1_555 yes
C(24) H(24A) 1.0850(3) 1_555 1_555 yes
C(24) H(24B) 1.0860(2) 1_555 1_555 yes
C(24) H(24C) 1.0880(2) 1_555 1_555 yes
C(111) C(112) 1.3984(2) 1_555 1_555 yes
C(111) C(116) 1.4123(3) 1_555 1_555 yes
C(113) C(114) 1.4551(3) 1_555 1_555 yes
C(114) C(115) 1.3597(3) 1_555 1_555 yes
C(115) C(116) 1.5165(3) 1_555 1_555 yes

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C(115) O(5) H(5) 107.36(2) 1_555 1_555 1_555 yes
C(124) N(125) C(126) 122.620(18) 1_555 1_555 1_555 yes
C(124) N(125) H(125) 119.540(18) 1_555 1_555 1_555 yes
C(126) N(125) H(125) 117.819(18) 1_555 1_555 1_555 yes
C(122) C(121) C(126) 119.143(18) 1_555 1_555 1_555 yes
C(122) C(121) H(121) 123.384(19) 1_555 1_555 1_555 yes
C(126) C(121) H(121) 117.47(2) 1_555 1_555 1_555 yes
C(121) C(122) C(123) 118.481(18) 1_555 1_555 1_555 yes
C(121) C(122) C(22) 120.865(19) 1_555 1_555 1_555 yes
C(123) C(122) C(22) 120.65(2) 1_555 1_555 1_555 yes
C(122) C(123) C(124) 120.624(19) 1_555 1_555 1_555 yes
C(122) C(123) H(123) 118.949(19) 1_555 1_555 1_555 yes
C(124) C(123) H(123) 120.254(19) 1_555 1_555 1_555 yes
N(125) C(124) C(123) 118.589(18) 1_555 1_555 1_555 yes
N(125) C(124) C(24) 118.677(19) 1_555 1_555 1_555 yes
C(123) C(124) C(24) 122.726(19) 1_555 1_555 1_555 yes
N(125) C(126) C(121) 120.498(19) 1_555 1_555 1_555 yes
N(125) C(126) H(126) 116.111(19) 1_555 1_555 1_555 yes
C(121) C(126) H(126) 123.294(19) 1_555 1_555 1_555 yes
C(122) C(22) H(22A) 111.13(2) 1_555 1_555 1_555 yes
C(122) C(22) H(22B) 110.11(2) 1_555 1_555 1_555 yes
C(122) C(22) H(22C) 109.30(2) 1_555 1_555 1_555 yes
H(22A) C(22) H(22B) 108.21(2) 1_555 1_555 1_555 yes
H(22A) C(22) H(22C) 108.97(2) 1_555 1_555 1_555 yes
H(22B) C(22) H(22C) 109.08(2) 1_555 1_555 1_555 yes
C(124) C(24) H(24A) 111.83(2) 1_555 1_555 1_555 yes
C(124) C(24) H(24B) 110.431(19) 1_555 1_555 1_555 yes
C(124) C(24) H(24C) 108.723(19) 1_555 1_555 1_555 yes
H(24A) C(24) H(24B) 107.13(2) 1_555 1_555 1_555 yes
H(24A) C(24) H(24C) 111.11(2) 1_555 1_555 1_555 yes
H(24B) C(24) H(24C) 107.53(2) 1_555 1_555 1_555 yes
CL(1) C(111) C(112) 119.205(14) 1_555 1_555 1_555 yes
CL(1) C(111) C(116) 117.790(14) 1_555 1_555 1_555 yes
C(112) C(111) C(116) 122.973(17) 1_555 1_555 1_555 yes
O(2) C(112) C(111) 125.65(2) 1_555 1_555 1_555 yes
O(3) C(113) C(114) 123.26(2) 1_555 1_555 1_555 yes
CL(2) C(114) C(113) 118.096(14) 1_555 1_555 1_555 yes
CL(2) C(114) C(115) 121.341(15) 1_555 1_555 1_555 yes
C(113) C(114) C(115) 120.559(17) 1_555 1_555 1_555 yes
O(5) C(115) C(114) 122.617(19) 1_555 1_555 1_555 yes
O(5) C(115) C(116) 115.783(17) 1_555 1_555 1_555 yes
C(114) C(115) C(116) 121.600(16) 1_555 1_555 1_555 yes
O(6) C(116) C(111) 125.54(2) 1_555 1_555 1_555 yes
O(6) C(116) C(115) 116.302(19) 1_555 1_555 1_555 yes
C(111) C(116) C(115) 118.162(15) 1_555 1_555 1_555 yes

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
H(5) O(5) C(115) C(114) -179.14(3) 1_555 1_555 1_555 1_555 yes
H(5) O(5) C(115) C(116) 1.065(17) 1_555 1_555 1_555 1_555 yes
C(124) N(125) C(126) C(121) -1.73(2) 1_555 1_555 1_555 1_555 yes
C(126) N(125) C(124) C(123) -0.06(2) 1_555 1_555 1_555 1_555 yes
C(126) N(125) C(124) C(24) 178.96(3) 1_555 1_555 1_555 1_555 yes
C(124) N(125) C(126) H(126) 174.80(3) 1_555 1_555 1_555 1_555 yes
H(125) N(125) C(124) C(123) -178.33(3) 1_555 1_555 1_555 1_555 yes
H(125) N(125) C(124) C(24) 0.694(18) 1_555 1_555 1_555 1_555 yes
H(125) N(125) C(126) C(121) 176.57(3) 1_555 1_555 1_555 1_555 yes
H(125) N(125) C(126) H(126) -6.901(17) 1_555 1_555 1_555 1_555 yes
C(122) C(121) C(126) N(125) 1.84(2) 1_555 1_555 1_555 1_555 yes
C(126) C(121) C(122) C(123) -0.22(2) 1_555 1_555 1_555 1_555 yes
C(126) C(121) C(122) C(22) -179.67(3) 1_555 1_555 1_555 1_555 yes
C(122) C(121) C(126) H(126) -174.44(3) 1_555 1_555 1_555 1_555 yes
H(121) C(121) C(122) C(123) -179.48(3) 1_555 1_555 1_555 1_555 yes
H(121) C(121) C(122) C(22) 1.06(2) 1_555 1_555 1_555 1_555 yes
H(121) C(121) C(126) N(125) -178.85(3) 1_555 1_555 1_555 1_555 yes
H(121) C(121) C(126) H(126) 4.874(19) 1_555 1_555 1_555 1_555 yes
C(121) C(122) C(123) C(124) -1.55(2) 1_555 1_555 1_555 1_555 yes
C(121) C(122) C(123) H(123) -176.80(3) 1_555 1_555 1_555 1_555 yes
C(121) C(122) C(22) H(22A) -151.71(3) 1_555 1_555 1_555 1_555 yes
C(121) C(122) C(22) H(22B) 88.40(3) 1_555 1_555 1_555 1_555 yes
C(121) C(122) C(22) H(22C) -31.41(2) 1_555 1_555 1_555 1_555 yes
C(22) C(122) C(123) C(124) 177.91(3) 1_555 1_555 1_555 1_555 yes
C(22) C(122) C(123) H(123) 2.660(19) 1_555 1_555 1_555 1_555 yes
C(123) C(122) C(22) H(22A) 28.84(2) 1_555 1_555 1_555 1_555 yes
C(123) C(122) C(22) H(22B) -91.05(3) 1_555 1_555 1_555 1_555 yes
C(123) C(122) C(22) H(22C) 149.14(3) 1_555 1_555 1_555 1_555 yes
C(122) C(123) C(124) N(125) 1.713(19) 1_555 1_555 1_555 1_555 yes
C(122) C(123) C(124) C(24) -177.27(3) 1_555 1_555 1_555 1_555 yes
H(123) C(123) C(124) N(125) 176.90(3) 1_555 1_555 1_555 1_555 yes
H(123) C(123) C(124) C(24) -2.086(19) 1_555 1_555 1_555 1_555 yes
N(125) C(124) C(24) H(24A) -8.901(19) 1_555 1_555 1_555 1_555 yes
N(125) C(124) C(24) H(24B) 110.29(3) 1_555 1_555 1_555 1_555 yes
N(125) C(124) C(24) H(24C) -131.96(3) 1_555 1_555 1_555 1_555 yes
C(123) C(124) C(24) H(24A) 170.08(3) 1_555 1_555 1_555 1_555 yes
C(123) C(124) C(24) H(24B) -70.72(2) 1_555 1_555 1_555 1_555 yes
C(123) C(124) C(24) H(24C) 47.03(2) 1_555 1_555 1_555 1_555 yes
CL(1) C(111) C(112) O(2) -1.327(18) 1_555 1_555 1_555 1_555 yes
CL(1) C(111) C(116) O(6) -1.42(2) 1_555 1_555 1_555 1_555 yes
CL(1) C(111) C(116) C(115) 178.84(2) 1_555 1_555 1_555 1_555 yes
C(116) C(111) C(112) O(2) -179.24(3) 1_555 1_555 1_555 1_555 yes
C(112) C(111) C(116) O(6) 176.52(3) 1_555 1_555 1_555 1_555 yes
C(112) C(111) C(116) C(115) -3.214(17) 1_555 1_555 1_555 1_555 yes
O(3) C(113) C(114) CL(2) 0.066(19) 1_555 1_555 1_555 1_555 yes
O(3) C(113) C(114) C(115) -179.18(3) 1_555 1_555 1_555 1_555 yes
CL(2) C(114) C(115) O(5) -1.738(17) 1_555 1_555 1_555 1_555 yes
CL(2) C(114) C(115) C(116) 178.04(3) 1_555 1_555 1_555 1_555 yes
C(113) C(114) C(115) O(5) 177.48(3) 1_555 1_555 1_555 1_555 yes
C(113) C(114) C(115) C(116) -2.736(17) 1_555 1_555 1_555 1_555 yes
O(5) C(115) C(116) O(6) 4.55(2) 1_555 1_555 1_555 1_555 yes
O(5) C(115) C(116) C(111) -175.69(3) 1_555 1_555 1_555 1_555 yes
C(114) C(115) C(116) O(6) -175.24(3) 1_555 1_555 1_555 1_555 yes
C(114) C(115) C(116) C(111) 4.520(18) 1_555 1_555 1_555 1_555 yes
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_(2,4)_neutron
_database_code_depnum_ccdc_archive 'CCDC 1478077'
_audit_update_record             
;
2016-05-04 deposited with the CCDC.
2016-06-13 downloaded from the CCDC.
;

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         
;
C6 H Cl2 O4, C7 H10 N 
;
_chemical_formula_sum            'C13 H11 Cl2 N O4'
_chemical_formula_weight         316.13
_chemical_compound_source        commercial


#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.0687(2)
_cell_length_b                   11.2561(4)
_cell_length_c                   11.6281(3)
_cell_angle_alpha                96.274(2)
_cell_angle_beta                 91.960(2)
_cell_angle_gamma                90.6090(10)
_cell_volume                     659.00(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7496
_cell_measurement_theta_min      3.192
_cell_measurement_theta_max      62.072
_cell_measurement_wavelength     0.9484

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          6
_exptl_crystal_size_mid          2
_exptl_crystal_size_min          2
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             194
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.1418
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.9484
_diffrn_radiation_probe          neutron
_diffrn_radiation_type           neutron
_diffrn_radiation_source         'nuclear reactor'

_diffrn_radiation_monochromator  Cu(220)
_diffrn_measurement_device_type  '4-circles Eulerian cradle'
_diffrn_measurement_method       'omega scans'
_diffrn_detector                 'multiwire proportional chamber'
_diffrn_detector_area_resol_mean 0.52
_diffrn_detector_details         
;
ILL cylindrically shaped large-area position sensitive detector 
with 120 by 30 deg detection angle (resolution: 0.4 by 0.64 pixels/mm)
;

_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7496
_diffrn_reflns_av_R_equivalents  0.029
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       1
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.192
_diffrn_reflns_theta_max         62.072
_diffrn_reflns_theta_full        34.683
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.839
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.839
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.839
_reflns_Friedel_coverage         0
_reflns_number_total             7496
_reflns_number_gt                6367
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'ILL-MAD software'
_computing_cell_refinement       'Dirax (Duisenberg, 1992)'
_computing_data_reduction        'PFIND, RETREAT (Wilkinson et al.,1988)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_atom_sites_solution_hydrogens   difmap

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+0.1640P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0377(7)
_refine_ls_number_reflns         7496
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0292
_refine_ls_wR_factor_ref         0.0623
_refine_ls_wR_factor_gt          0.0592
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.852
_refine_diff_density_min         -0.852
_refine_diff_density_rms         0.165

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_length_neutron
_atom_type_scat_source
C C 0.0000 0.0000 6.646 'Neutron Data Booklet Table 1.1-8'
H H 0.0000 0.0000 -3.739 'Neutron Data Booklet Table 1.1-8'
N N 0.0000 0.0000 9.36 'Neutron Data Booklet Table 1.1-8'
O O 0.0000 0.0000 5.803 'Neutron Data Booklet Table 1.1-8'
Cl Cl 0.0000 0.0000 9.577 'Neutron Data Booklet Table 1.1-8'

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 0.64455(6) 0.89047(2) 0.08935(2) 0.01444(5) Uani 1 1 d . . . . .
Cl2 Cl -0.22963(6) 0.57335(2) 0.29505(2) 0.01542(5) Uani 1 1 d . . . . .
O2 O 0.27071(10) 0.96795(4) 0.27812(4) 0.01544(7) Uani 1 1 d . . . . .
O3 O -0.10144(11) 0.83163(4) 0.35949(4) 0.01613(8) Uani 1 1 d . . . . .
O5 O 0.15879(11) 0.49589(4) 0.11481(4) 0.01523(7) Uani 1 1 d . . . . .
O6 O 0.49851(12) 0.63401(4) 0.02163(4) 0.01673(8) Uani 1 1 d . . . . .
N125 N -0.15005(6) 1.10798(2) 0.32318(2) 0.01284(5) Uani 1 1 d . . . . .
C121 C -0.46890(9) 1.20020(3) 0.44654(3) 0.01424(6) Uani 1 1 d . . . . .
C122 C -0.53284(9) 1.27736(3) 0.36299(3) 0.01311(6) Uani 1 1 d . . . . .
C123 C -0.39949(9) 1.26514(3) 0.25932(3) 0.01349(6) Uani 1 1 d . . . . .
C124 C -0.20341(8) 1.18017(3) 0.24043(3) 0.01215(6) Uani 1 1 d . . . . .
C126 C -0.27872(9) 1.11495(3) 0.42343(3) 0.01388(6) Uani 1 1 d . . . . .
C22 C -0.73751(10) 1.37177(4) 0.38497(4) 0.01818(7) Uani 1 1 d . . . . .
C24 C -0.04669(10) 1.16709(4) 0.13312(3) 0.01627(7) Uani 1 1 d . . . . .
C111 C 0.40724(8) 0.80637(3) 0.14823(3) 0.01132(6) Uani 1 1 d . . . . .
C112 C 0.25176(8) 0.86095(3) 0.23534(3) 0.01128(6) Uani 1 1 d . . . . .
C113 C 0.03596(8) 0.78395(3) 0.28377(3) 0.01151(6) Uani 1 1 d . . . . .
C114 C 0.00893(8) 0.65853(3) 0.23855(3) 0.01197(6) Uani 1 1 d . . . . .
C115 C 0.17009(8) 0.61019(3) 0.15528(3) 0.01157(6) Uani 1 1 d . . . . .
C116 C 0.37413(8) 0.68537(3) 0.10256(3) 0.01146(6) Uani 1 1 d . . . . .
H121 H -0.5710(3) 1.20519(11) 0.52773(8) 0.0313(2) Uani 1 1 d . . . . .
H123 H -0.4445(3) 1.32215(10) 0.19139(9) 0.0312(2) Uani 1 1 d . . . . .
H125 H 0.0006(2) 1.04351(8) 0.30937(8) 0.02464(16) Uani 1 1 d . . . . .
H126 H -0.2218(3) 1.05140(10) 0.48327(9) 0.0321(2) Uani 1 1 d . . . . .
H22A H -0.8256(4) 1.39627(16) 0.30481(12) 0.0496(4) Uani 1 1 d . . . . .
H22B H -0.6507(3) 1.45158(14) 0.43140(19) 0.0545(4) Uani 1 1 d . . . . .
H22C H -0.8922(3) 1.34318(15) 0.43874(16) 0.0485(4) Uani 1 1 d . . . . .
H24A H 0.1188(3) 1.10777(16) 0.14094(12) 0.0448(3) Uani 1 1 d . . . . .
H24B H -0.1721(3) 1.13173(16) 0.05943(9) 0.0430(3) Uani 1 1 d . . . . .
H24C H 0.0268(4) 1.25365(12) 0.11427(13) 0.0456(3) Uani 1 1 d . . . . .
H5 H 0.2936(2) 0.47882(9) 0.05570(8) 0.02868(19) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   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 C111 1.7279(5) . ?
Cl2 C114 1.7264(5) . ?
O2 C112 1.2533(6) . ?
O3 C113 1.2228(6) . ?
O5 C115 1.3207(6) . ?
O5 H5 0.9912(11) . ?
O6 C116 1.2437(6) . ?
N125 C124 1.3480(4) . ?
N125 C126 1.3504(4) . ?
N125 H125 1.0631(10) . ?
C121 C126 1.3796(6) . ?
C121 C122 1.4043(5) . ?
C121 H121 1.0885(10) . ?
C122 C123 1.3966(5) . ?
C122 C22 1.5010(6) . ?
C123 C124 1.3929(6) . ?
C123 H123 1.0904(9) . ?
C124 C24 1.4966(5) . ?
C126 H126 1.0855(9) . ?
C22 H22A 1.0837(14) . ?
C22 H22B 1.0777(16) . ?
C22 H22C 1.0869(15) . ?
C24 H24A 1.0850(14) . ?
C24 H24B 1.0859(13) . ?
C24 H24C 1.0866(13) . ?
C111 C112 1.3976(5) . ?
C111 C116 1.4128(5) . ?
C112 C113 1.5471(5) . ?
C113 C114 1.4550(5) . ?
C114 C115 1.3599(5) . ?
C115 C116 1.5165(5) . ?

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
C115 O5 H5 109.82(8) . . ?
C124 N125 C126 122.64(3) . . ?
C124 N125 H125 118.73(6) . . ?
C126 N125 H125 118.64(6) . . ?
C126 C121 C122 119.17(3) . . ?
C126 C121 H121 119.86(7) . . ?
C122 C121 H121 120.95(7) . . ?
C123 C122 C121 118.47(4) . . ?
C123 C122 C22 120.67(3) . . ?
C121 C122 C22 120.86(3) . . ?
C124 C123 C122 120.70(3) . . ?
C124 C123 H123 118.21(7) . . ?
C122 C123 H123 121.09(7) . . ?
N125 C124 C123 118.52(3) . . ?
N125 C124 C24 118.70(3) . . ?
C123 C124 C24 122.77(3) . . ?
N125 C126 C121 120.46(3) . . ?
N125 C126 H126 116.36(7) . . ?
C121 C126 H126 123.17(7) . . ?
C122 C22 H22A 111.55(9) . . ?
C122 C22 H22B 110.58(10) . . ?
H22A C22 H22B 107.51(16) . . ?
C122 C22 H22C 111.65(9) . . ?
H22A C22 H22C 109.23(15) . . ?
H22B C22 H22C 106.10(16) . . ?
C124 C24 H24A 111.75(7) . . ?
C124 C24 H24B 109.91(9) . . ?
H24A C24 H24B 108.71(14) . . ?
C124 C24 H24C 110.50(9) . . ?
H24A C24 H24C 109.04(14) . . ?
H24B C24 H24C 106.78(13) . . ?
C112 C111 C116 122.97(3) . . ?
C112 C111 Cl1 119.22(3) . . ?
C116 C111 Cl1 117.77(3) . . ?
O2 C112 C111 125.65(4) . . ?
O2 C112 C113 116.47(4) . . ?
C111 C112 C113 117.88(3) . . ?
O3 C113 C114 123.30(4) . . ?
O3 C113 C112 118.03(4) . . ?
C114 C113 C112 118.66(3) . . ?
C115 C114 C113 120.57(4) . . ?
C115 C114 Cl2 121.35(3) . . ?
C113 C114 Cl2 118.07(3) . . ?
O5 C115 C114 122.57(4) . . ?
O5 C115 C116 115.81(4) . . ?
C114 C115 C116 121.61(3) . . ?
O6 C116 C111 125.56(4) . . ?
O6 C116 C115 116.28(4) . . ?
C111 C116 C115 118.16(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
C126 C121 C122 C123 -0.35(6) . . . . ?
C126 C121 C122 C22 -179.66(4) . . . . ?
C121 C122 C123 C124 -1.45(6) . . . . ?
C22 C122 C123 C124 177.87(4) . . . . ?
C126 N125 C124 C123 -0.09(6) . . . . ?
C126 N125 C124 C24 178.90(4) . . . . ?
C122 C123 C124 N125 1.69(6) . . . . ?
C122 C123 C124 C24 -177.26(4) . . . . ?
C124 N125 C126 C121 -1.74(6) . . . . ?
C122 C121 C126 N125 1.92(6) . . . . ?
C116 C111 C112 O2 -179.24(4) . . . . ?
Cl1 C111 C112 O2 -1.42(6) . . . . ?
C116 C111 C112 C113 0.51(5) . . . . ?
Cl1 C111 C112 C113 178.33(3) . . . . ?
O2 C112 C113 O3 0.21(6) . . . . ?
C111 C112 C113 O3 -179.57(4) . . . . ?
O2 C112 C113 C114 -178.88(4) . . . . ?
C111 C112 C113 C114 1.34(5) . . . . ?
O3 C113 C114 C115 -179.13(4) . . . . ?
C112 C113 C114 C115 -0.09(5) . . . . ?
O3 C113 C114 Cl2 0.02(6) . . . . ?
C112 C113 C114 Cl2 179.06(3) . . . . ?
C113 C114 C115 O5 177.49(4) . . . . ?
Cl2 C114 C115 O5 -1.64(6) . . . . ?
C113 C114 C115 C116 -2.86(6) . . . . ?
Cl2 C114 C115 C116 178.02(3) . . . . ?
C112 C111 C116 O6 176.50(4) . . . . ?
Cl1 C111 C116 O6 -1.34(6) . . . . ?
C112 C111 C116 C115 -3.34(5) . . . . ?
Cl1 C111 C116 C115 178.81(3) . . . . ?
O5 C115 C116 O6 4.44(6) . . . . ?
C114 C115 C116 O6 -175.23(4) . . . . ?
O5 C115 C116 C111 -175.70(4) . . . . ?
C114 C115 C116 C111 4.62(5) . . . . ?

####################################################################### 
# 
# 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_2_(2,4)_shelx
_database_code_depnum_ccdc_archive 'CCDC 1478078'
_audit_update_record             
;
2016-05-04 deposited with the CCDC.
2016-06-13 downloaded from the CCDC.
;

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         
;
C6 Cl2 O4, 2(C7 H10 N) 
;
_chemical_formula_sum            'C20 H20 Cl2 N2 O4'
_chemical_formula_weight         423.28
_chemical_compound_source        commercial

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P c a b'
_space_group_name_Hall           '-P 2bc 2ac'
_space_group_IT_number           61

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

_cell_length_a                   7.5644(5)
_cell_length_b                   15.7136(10)
_cell_length_c                   16.6651(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1980.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9962
_cell_measurement_theta_min      2.444
_cell_measurement_theta_max      50.238
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             880
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.357
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4845
_exptl_absorpt_correction_T_max  0.7495
_exptl_absorpt_process_details   'SADABS, Bruker(2001)'
#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      0.247579E-1
_diffrn_orient_matrix_UB_21      -0.0986310E-1
_diffrn_orient_matrix_UB_31      0.846542E-1
_diffrn_orient_matrix_UB_12      0.360962E-1
_diffrn_orient_matrix_UB_22      0.388970E-1
_diffrn_orient_matrix_UB_32      0.347624E-1
_diffrn_orient_matrix_UB_13      -0.479744E-1
_diffrn_orient_matrix_UB_23      0.156672E-1
_diffrn_orient_matrix_UB_33      0.322845E-1
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_reflns_av_R_equivalents  0.0837
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_number            9962
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         2.444
_diffrn_reflns_theta_max         50.238
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.926
_diffrn_measured_fraction_theta_max 0.949
_diffrn_reflns_Laue_measured_fraction_full 0.926
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_point_group_measured_fraction_full 0.926
_diffrn_reflns_point_group_measured_fraction_max 0.949
_reflns_Friedel_coverage         0
_reflns_number_total             9962
_reflns_number_gt                7830
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
 Scaled and merged with Sortav
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0697P)²+0.0022P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         9962
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0368
_refine_ls_wR_factor_ref         0.1079
_refine_ls_wR_factor_gt          0.1018
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.598
_refine_diff_density_min         -0.468
_refine_diff_density_rms         0.067

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 -0.57111(2) 0.61179(2) 0.15548(2) 0.01731(3) Uani 1 1 d . . . . .
O2 O -0.79782(5) 0.59581(3) 0.01087(2) 0.01997(6) Uani 1 1 d . . . . .
O3 O -0.73757(5) 0.50209(3) -0.12057(2) 0.01997(6) Uani 1 1 d . . . . .
N125 N -1.08172(5) 0.60581(2) -0.08152(2) 0.01492(5) Uani 1 1 d . . . . .
C121 C -1.25124(6) 0.59179(3) -0.20056(3) 0.01687(6) Uani 1 1 d . . . . .
C122 C -1.37830(6) 0.64730(3) -0.16923(3) 0.01642(6) Uani 1 1 d . . . . .
C123 C -1.35059(6) 0.68004(3) -0.09243(3) 0.01706(6) Uani 1 1 d . . . . .
C124 C -1.20088(5) 0.65894(3) -0.04812(2) 0.01439(5) Uani 1 1 d . . . . .
C126 C -1.10435(6) 0.57224(3) -0.15528(3) 0.01722(6) Uani 1 1 d . . . . .
C22 C -1.53921(8) 0.67065(4) -0.21716(4) 0.02565(9) Uani 1 1 d . . . . .
H22A H -1.6345 0.6329 -0.2037 0.038 Uiso 1 1 calc R U . . .
H22B H -1.5131 0.6659 -0.2734 0.038 Uiso 1 1 calc R U . . .
H22C H -1.5729 0.7281 -0.205 0.038 Uiso 1 1 calc R U . . .
C24 C -1.16644(6) 0.69290(3) 0.03436(3) 0.01822(6) Uani 1 1 d . . . . .
C111 C -0.53215(5) 0.55102(3) 0.07015(2) 0.01385(5) Uani 1 1 d . . . . .
C112 C -0.65758(5) 0.55274(2) 0.00883(2) 0.01388(5) Uani 1 1 d . . . . .
C113 C -0.62392(5) 0.49875(3) -0.06695(2) 0.01396(5) Uani 1 1 d . . . . .
H121 H -1.2593(19) 0.5665(8) -0.2506(9) 0.029(3) Uiso 1 1 d . . . . .
H123 H -1.4345(17) 0.7178(9) -0.0698(9) 0.028(3) Uiso 1 1 d . . . . .
H125 H -0.971(3) 0.5958(12) -0.0527(12) 0.057(5) Uiso 1 1 d . . . . .
H126 H -1.0151(19) 0.5351(9) -0.1723(8) 0.029(3) Uiso 1 1 d . . . . .
H24A H -1.045(2) 0.6820(12) 0.0513(11) 0.044(4) Uiso 1 1 d . . . . .
H24B H -1.1938(19) 0.7535(10) 0.0364(10) 0.038(4) Uiso 1 1 d . . . . .
H24C H -1.227(2) 0.6657(11) 0.0687(10) 0.044(4) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   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 C111 1.7381(4) . ?
O2 C112 1.2588(5) . ?
O3 C113 1.2411(5) . ?
N125 C126 1.3486(6) . ?
N125 C124 1.3488(5) . ?
N125 H125 0.98(2) . ?
C121 C126 1.3778(6) . ?
C121 C122 1.3990(6) . ?
C121 H121 0.925(15) . ?
C122 C123 1.3952(6) . ?
C122 C22 1.5014(7) . ?
C123 C124 1.3920(6) . ?
C123 H123 0.948(14) . ?
C124 C24 1.4973(6) . ?
C126 H126 0.936(14) . ?
C22 H22A 0.96 . ?
C22 H22B 0.96 . ?
C22 H22C 0.96 . ?
C24 H24A 0.973(18) . ?
C24 H24B 0.975(16) . ?
C24 H24C 0.851(17) . ?
C111 C112 1.3947(5) . ?
C111 C113 1.4171(5) 5_465 ?
C112 C113 1.5426(5) . ?
C113 C111 1.4171(5) 5_465 ?

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
C126 N125 C124 122.24(4) . . ?
C126 N125 H125 119.6(12) . . ?
C124 N125 H125 117.9(12) . . ?
C126 C121 C122 119.26(4) . . ?
C126 C121 H121 116.8(9) . . ?
C122 C121 H121 123.9(9) . . ?
C123 C122 C121 117.97(4) . . ?
C123 C122 C22 121.31(4) . . ?
C121 C122 C22 120.72(4) . . ?
C124 C123 C122 121.40(4) . . ?
C124 C123 H123 118.9(8) . . ?
C122 C123 H123 119.7(8) . . ?
N125 C124 C123 118.17(4) . . ?
N125 C124 C24 118.89(4) . . ?
C123 C124 C24 122.94(4) . . ?
N125 C126 C121 120.95(4) . . ?
N125 C126 H126 115.3(8) . . ?
C121 C126 H126 123.7(8) . . ?
C122 C22 H22A 109.5 . . ?
C122 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C122 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C124 C24 H24A 111.6(11) . . ?
C124 C24 H24B 110.1(9) . . ?
H24A C24 H24B 111.2(14) . . ?
C124 C24 H24C 110.1(11) . . ?
H24A C24 H24C 103.1(15) . . ?
H24B C24 H24C 110.6(15) . . ?
C112 C111 C113 123.36(3) . 5_465 ?
C112 C111 Cl1 118.26(3) . . ?
C113 C111 Cl1 118.38(3) 5_465 . ?
O2 C112 C111 124.34(4) . . ?
O2 C112 C113 117.18(3) . . ?
C111 C112 C113 118.48(3) . . ?
O3 C113 C111 124.98(4) . 5_465 ?
O3 C113 C112 116.86(3) . . ?
C111 C113 C112 118.15(3) 5_465 . ?

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
C126 C121 C122 C123 -0.54(7) . . . . ?
C126 C121 C122 C22 179.44(5) . . . . ?
C121 C122 C123 C124 0.44(7) . . . . ?
C22 C122 C123 C124 -179.54(5) . . . . ?
C126 N125 C124 C123 -0.79(6) . . . . ?
C126 N125 C124 C24 179.51(4) . . . . ?
C122 C123 C124 N125 0.21(7) . . . . ?
C122 C123 C124 C24 179.89(4) . . . . ?
C124 N125 C126 C121 0.71(7) . . . . ?
C122 C121 C126 N125 -0.01(7) . . . . ?
C113 C111 C112 O2 179.24(4) 5_465 . . . ?
Cl1 C111 C112 O2 0.28(6) . . . . ?
C113 C111 C112 C113 -0.88(6) 5_465 . . . ?
Cl1 C111 C112 C113 -179.84(3) . . . . ?
O2 C112 C113 O3 0.30(6) . . . . ?
C111 C112 C113 O3 -179.58(4) . . . . ?
O2 C112 C113 C111 -179.27(4) . . . 5_465 ?
C111 C112 C113 C111 0.84(6) . . . 5_465 ?

####################################################################### 
# 
# 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_2_(2,4)_xd
_database_code_depnum_ccdc_archive 'CCDC 1478079'
_audit_update_record             
;
2016-05-04 deposited with the CCDC.
2016-06-13 downloaded from the CCDC.
;

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         
;
C6 Cl2 O4, 2(C7 H10 N) 
;
_chemical_formula_sum            'C20 H20 Cl2 N2 O4'
_chemical_formula_weight         423.28
_chemical_compound_source        commercial

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P c a b'
_space_group_name_Hall           '-P 2bc 2ac'
_space_group_IT_number           61

loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2-Y,1/2+Z
3 1/2+X,-Y,1/2-Z
4 1/2-X,1/2+Y,-Z
5 -X,-Y,-Z
6 +X,1/2+Y,1/2-Z
7 1/2-X,+Y,1/2+Z
8 1/2+X,1/2-Y,+Z

_cell_length_a                   7.5644(5)
_cell_length_b                   15.7136(10)
_cell_length_c                   16.6651(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1980.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9962
_cell_measurement_theta_min      2.4
_cell_measurement_theta_max      50.24
_cell_measurement_wavelength     0.71073


_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             880
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.357
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4845
_exptl_absorpt_correction_T_max  0.7495
_exptl_absorpt_process_details   'SADABS, Bruker(2001)'
#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      0.247579E-1
_diffrn_orient_matrix_UB_21      -0.0986310E-1
_diffrn_orient_matrix_UB_31      0.846542E-1
_diffrn_orient_matrix_UB_12      0.360962E-1
_diffrn_orient_matrix_UB_22      0.388970E-1
_diffrn_orient_matrix_UB_32      0.347624E-1
_diffrn_orient_matrix_UB_13      -0.479744E-1
_diffrn_orient_matrix_UB_23      0.156672E-1
_diffrn_orient_matrix_UB_33      0.322845E-1
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_reflns_av_R_equivalents  0.0837
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_number            9962
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         2.44
_diffrn_reflns_theta_max         50.24
_diffrn_reflns_theta_full        50.24
_diffrn_measured_fraction_theta_full 0.949
_diffrn_measured_fraction_theta_max 0.949
_reflns_number_total             9962
_reflns_number_gt                7830
_reflns_threshold_expression     >2σ(I)
_diffrn_reflns_reduction_process 
;
 Scaled and merged with Sortav
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
        ?
;
_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
        calc w1 = 1/[s²(Fo)]
;
_refine_ls_extinction_method     none
_refine_ls_number_reflns         8200
_refine_ls_number_parameters     378
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.056
_refine_ls_R_factor_gt           0.029
_refine_ls_wR_factor_ref         0.028
_refine_ls_goodness_of_fit_ref   1.447
_refine_ls_shift/su_max          0.00003
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.051

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, 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_symmetry_multiplicity
Cl(1) Cl -0.571113(12) 0.611792(6) 0.155477(5) 0.017 Uani 1 8
O(2) O -0.79775(6) 0.59573(3) 0.01094(3) 0.02 Uani 1 8
O(3) O -0.73752(6) 0.50206(3) -0.12051(2) 0.019 Uani 1 8
N(125) N -1.08170(5) 0.60582(2) -0.08152(2) 0.014 Uani 1 8
C(121) C -1.25129(5) 0.59176(3) -0.20057(2) 0.016 Uani 1 8
C(122) C -1.37841(5) 0.64732(2) -0.16925(2) 0.016 Uani 1 8
C(123) C -1.35067(5) 0.68010(2) -0.09239(2) 0.017 Uani 1 8
C(124) C -1.20086(5) 0.65894(2) -0.04811(2) 0.014 Uani 1 8
C(126) C -1.10426(5) 0.57221(3) -0.15528(2) 0.017 Uani 1 8
C(22) C -1.53911(6) 0.67059(4) -0.21713(3) 0.025 Uani 1 8
C(24) C -1.16642(5) 0.69289(2) 0.03436(2) 0.018 Uani 1 8
C(111) C -0.53219(4) 0.55104(2) 0.070183(18) 0.013 Uani 1 8
C(112) C -0.65755(4) 0.55272(2) 0.008839(19) 0.013 Uani 1 8
C(113) C -0.62391(4) 0.49873(2) -0.066934(18) 0.014 Uani 1 8
H(121) H -1.260979 0.562438 -0.259215 0.035 Uani 1 8
H(123) H -1.447343 0.72258 -0.066058 0.031 Uani 1 8
H(125) H -0.964894 0.595506 -0.050916 0.028 Uani 1 8
H(126) H -0.999362 0.530122 -0.174807 0.031 Uani 1 8
H(22A) H -1.522223 0.661705 -0.279656 0.042 Uani 1 8
H(22B) H -1.578981 0.73468 -0.209473 0.04 Uani 1 8
H(22C) H -1.643628 0.627248 -0.206293 0.04 Uani 1 8
H(24A) H -1.034418 0.681845 0.052798 0.036 Uani 1 8
H(24B) H -1.195742 0.758699 0.037563 0.038 Uani 1 8
H(24C) H -1.245454 0.659869 0.076575 0.038 Uani 1 8



#----------------------------------------------------------------------------#
#                   MULTIPOLE PARAMETERS                                     #
#----------------------------------------------------------------------------#

loop_
_atom_rho_multipole_atom_label
_atom_rho_multipole_coeff_Pv
_atom_rho_multipole_coeff_P00
_atom_rho_multipole_coeff_P11
_atom_rho_multipole_coeff_P1-1
_atom_rho_multipole_coeff_P10
_atom_rho_multipole_coeff_P20
_atom_rho_multipole_coeff_P21
_atom_rho_multipole_coeff_P2-1
_atom_rho_multipole_coeff_P22
_atom_rho_multipole_coeff_P2-2
_atom_rho_multipole_coeff_P30
_atom_rho_multipole_coeff_P31
_atom_rho_multipole_coeff_P3-1
_atom_rho_multipole_coeff_P32
_atom_rho_multipole_coeff_P3-2
_atom_rho_multipole_coeff_P33
_atom_rho_multipole_coeff_P3-3
_atom_rho_multipole_coeff_P40
_atom_rho_multipole_coeff_P41
_atom_rho_multipole_coeff_P4-1
_atom_rho_multipole_coeff_P42
_atom_rho_multipole_coeff_P4-2
_atom_rho_multipole_coeff_P43
_atom_rho_multipole_coeff_P4-3
_atom_rho_multipole_coeff_P44
_atom_rho_multipole_coeff_P4-4
_atom_rho_multipole_kappa
_atom_rho_multipole_kappa_prime0
_atom_rho_multipole_kappa_prime1
_atom_rho_multipole_kappa_prime2
_atom_rho_multipole_kappa_prime3
_atom_rho_multipole_kappa_prime4
Cl(1) 7.66(4) 0 0.039(15) -0.038(13) -0.059(16) -0.160(19) 0.05(2) -0.044(18)
-0.007(17) 0.017(18) 0.095(15) -0.020(15) -0.007(14) 0.019(14) 0.002(14)
-0.027(13) -0.054(14) 0.012(18) -0.025(18) 0.008(16) 0.027(17) -0.039(18)
0.003(17) -0.022(18) -0.002(16) -0.023(17) 0.983416 1 1 1 1 1
O(2) 6.12(2) 0 -0.011(14) 0.007(13) -0.086(13) -0.017(15) -0.013(15) 0.008(13)
-0.073(15) 0.003(15) 0.013(12) -0.002(12) 0.005(10) 0.053(12) -0.022(12)
-0.014(12) 0.030(12) 0 0 0 0 0 0 0 0 0 0.987955 0.995766 0.995766 0.995766
0.995766 0.995766
O(3) 6.12(2) 0 0.003(14) 0.013(12) -0.069(13) -0.006(15) 0.012(15) -0.012(13)
-0.079(15) 0.037(15) 0.047(12) -0.004(12) 0.003(11) 0.012(12) -0.013(12)
0.000(12) 0.005(12) 0 0 0 0 0 0 0 0 0 0.987955 0.995766 0.995766 0.995766
0.995766 0.995766
N(125) 5.05(4) 0 -0.008(16) -0.052(18) 0.008(14) -0.110(15) -0.002(15)
0.002(15) 0.001(15) 0.031(16) -0.010(15) 0.011(14) -0.007(14) 0.013(14)
-0.012(14) 0.203(14) 0.011(14) 0 0 0 0 0 0 0 0 0 0.990979 0.96394 0.96394
0.96394 0.96394 0.96394
C(121) 4.15(5) 0 0.04(2) 0.01(2) -0.005(18) -0.205(18) 0.006(18) -0.005(17)
-0.021(19) 0.007(19) 0.01(2) 0.02(2) 0.023(19) 0.00(2) 0.03(2) 0.26(2) 0.02(2)
0 0 0 0 0 0 0 0 0 0.985284 0.967548 0.967548 0.967548 0.967548 0.967548
C(122) 4.04(5) 0 0.01(2) 0.03(2) -0.005(19) -0.231(19) 0.004(19) 0.023(18)
0.02(2) 0.01(2) 0.02(2) 0.02(2) 0.022(19) 0.03(2) 0.00(2) 0.28(2) -0.01(2) 0 0
0 0 0 0 0 0 0 0.985284 0.967548 0.967548 0.967548 0.967548 0.967548
C(123) 4.05(5) 0 0.01(2) 0.04(2) -0.013(18) -0.174(18) 0.006(19) 0.001(17)
-0.02(2) 0.006(19) 0.01(2) 0.02(2) 0.035(19) 0.01(2) 0.01(2) 0.27(2) -0.04(2) 0
0 0 0 0 0 0 0 0 0.985284 0.967548 0.967548 0.967548 0.967548 0.967548
C(124) 4.10(5) 0 -0.067(19) -0.01(2) 0.011(17) -0.217(18) -0.005(17) -0.008(18)
-0.006(19) -0.008(19) -0.01(2) 0.030(19) 0.032(19) 0.00(2) 0.001(19) 0.29(2)
0.03(2) 0 0 0 0 0 0 0 0 0 0.985284 0.967548 0.967548 0.967548 0.967548 0.967548
C(126) 4.12(5) 0 0.02(2) -0.002(19) 0.018(19) -0.221(19) -0.010(18) 0.018(18)
0.044(18) 0.041(19) -0.03(2) 0.01(2) -0.01(2) 0.02(2) 0.00(2) 0.311(19)
-0.02(2) 0 0 0 0 0 0 0 0 0 0.985284 0.967548 0.967548 0.967548 0.967548
0.967548
C(22) 4.63(9) 0 0.11(3) 0.06(2) 0.10(2) 0.05(2) -0.09(2) -0.02(2) -0.08(2)
-0.05(2) 0.02(3) 0.09(3) 0.08(3) -0.16(3) -0.37(3) 0.09(3) -0.10(3) 0 0 0 0 0 0
0 0 0 0.975594 0.85438 0.85438 0.85438 0.85438 0.85438
C(24) 4.30(9) 0 0.11(2) 0.06(2) 0.07(2) 0.00(2) -0.03(2) -0.06(2) -0.04(2)
-0.09(2) 0.21(3) 0.00(2) 0.06(2) -0.05(2) -0.16(2) 0.04(3) -0.28(2) 0 0 0 0 0 0
0 0 0 0.975594 0.85438 0.85438 0.85438 0.85438 0.85438
C(111) 3.99(4) 0 0.03(2) -0.046(19) -0.004(17) -0.068(18) -0.001(18) -0.001(17)
0.048(18) 0.102(19) 0.01(2) 0.02(2) -0.020(19) 0.00(2) -0.02(2) 0.19(2)
-0.03(2) 0 0 0 0 0 0 0 0 0 0.990421 0.950331 0.950331 0.950331 0.950331
0.950331
C(112) 4.05(4) 0 -0.08(2) -0.037(19) 0.008(17) -0.273(18) 0.002(17) -0.028(17)
-0.110(19) 0.042(19) 0.01(2) 0.013(19) 0.035(19) -0.01(2) 0.00(2) 0.35(2)
0.03(2) 0 0 0 0 0 0 0 0 0 0.990421 0.950331 0.950331 0.950331 0.950331 0.950331
C(113) 4.06(4) 0 0.056(18) -0.017(19) 0.002(18) -0.270(19) -0.005(17)
-0.009(17) 0.065(19) 0.052(18) 0.01(2) 0.00(2) -0.02(2) 0.00(2) 0.02(2) 0.35(2)
-0.04(2) 0 0 0 0 0 0 0 0 0 0.990421 0.950331 0.950331 0.950331 0.950331
0.950331
H(121) 0.845(18) 0 -0.016(11) -0.018(10) 0.159(14) 0.077(17) 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0 0 0 1.171653 1.171653 1.171653 1.171653 1.171653 1.171653
H(123) 0.845(18) 0 -0.016(11) -0.018(10) 0.159(14) 0.077(17) 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0 0 0 1.171653 1.171653 1.171653 1.171653 1.171653 1.171653
H(125) 0.75(3) 0 0.042(18) -0.008(18) 0.07(2) 0.18(3) 0 0 0 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 1.171653 1.171653 1.171653 1.171653 1.171653 1.171653
H(126) 0.845(18) 0 -0.016(11) -0.018(10) 0.159(14) 0.077(17) 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0 0 0 1.171653 1.171653 1.171653 1.171653 1.171653 1.171653
H(22A) 0.64(2) 0 -0.034(15) -0.044(15) 0.081(17) -0.05(2) 0 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0 1.128107 1.128107 1.128107 1.128107 1.128107 1.128107
H(22B) 0.64(2) 0 -0.034(15) -0.044(15) 0.081(17) -0.05(2) 0 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0 1.128107 1.128107 1.128107 1.128107 1.128107 1.128107
H(22C) 0.64(2) 0 -0.034(15) -0.044(15) 0.081(17) -0.05(2) 0 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0 1.128107 1.128107 1.128107 1.128107 1.128107 1.128107
H(24A) 0.79(2) 0 0.006(14) -0.055(13) 0.112(16) 0.04(2) 0 0 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 1.128107 1.128107 1.128107 1.128107 1.128107 1.128107
H(24B) 0.79(2) 0 0.006(14) -0.055(13) 0.112(16) 0.04(2) 0 0 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 1.128107 1.128107 1.128107 1.128107 1.128107 1.128107
H(24C) 0.79(2) 0 0.006(14) -0.055(13) 0.112(16) 0.04(2) 0 0 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 1.128107 1.128107 1.128107 1.128107 1.128107 1.128107

loop_
_atom_local_axes_atom_label
_atom_local_axes_atom0
_atom_local_axes_ax1
_atom_local_axes_atom1
_atom_local_axes_atom2
_atom_local_axes_ax2
CL(1) C(111) Z CL(1) C(112) Y
O(2) C(112) Z O(2) H(125) Y
O(3) C(113) Z O(3) H(126) Y
N(125) C(124) X N(125) C(126) Y
C(121) C(122) X C(121) C(126) Y
C(122) C(123) X C(122) C(121) Y
C(123) C(122) X C(123) C(124) Y
C(124) N(125) X C(124) C(123) Y
C(126) C(121) X C(126) N(125) Y
C(22) H(22B) Z C(22) H(22C) Y
C(24) H(24C) Z C(24) H(24B) Y
C(111) C(112) X C(111) CL(1) Y
C(112) C(113) X C(112) C(111) Y
C(113) O(3) X C(113) C(112) Y
H(121) C(121) Z H(121) C(126) Y
H(123) C(123) Z H(123) C(124) Y
H(125) N(125) Z H(125) O(2) Y
H(126) C(126) Z H(126) N(125) Y
H(22A) C(22) Z H(22A) H(22C) Y
H(22B) C(22) Z H(22B) H(22A) Y
H(22C) C(22) Z H(22C) H(22A) Y
H(24A) C(24) Z H(24A) H(24C) Y
H(24B) C(24) Z H(24B) H(24C) Y
H(24C) C(24) Z H(24C) H(24A) Y


#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
CL(1) C(111) 1.7374(3) 1_555 1_555 yes
O(2) C(112) 1.2580(5) 1_555 1_555 yes
O(3) C(113) 1.2403(5) 1_555 1_555 yes
N(125) C(124) 1.3488(5) 1_555 1_555 yes
N(125) C(126) 1.3487(5) 1_555 1_555 yes
N(125) H(125) 1.0330(3) 1_555 1_555 yes
C(121) C(122) 1.3997(5) 1_555 1_555 yes
C(121) C(126) 1.3788(5) 1_555 1_555 yes
C(121) H(121) 1.0830(4) 1_555 1_555 yes
C(122) C(123) 1.3963(5) 1_555 1_555 yes
C(122) C(22) 1.4995(6) 1_555 1_555 yes
C(123) C(124) 1.3926(5) 1_555 1_555 yes
C(123) H(123) 1.0830(4) 1_555 1_555 yes
C(124) C(24) 1.4971(5) 1_555 1_555 yes
C(126) H(126) 1.0830(4) 1_555 1_555 yes
C(22) H(22A) 1.0590(5) 1_555 1_555 yes
C(22) H(22B) 1.0590(6) 1_555 1_555 yes
C(22) H(22C) 1.0590(6) 1_555 1_555 yes
C(24) H(24A) 1.0590(4) 1_555 1_555 yes
C(24) H(24B) 1.0590(4) 1_555 1_555 yes
C(24) H(24C) 1.0590(4) 1_555 1_555 yes
C(111) C(112) 1.3946(4) 1_555 1_555 yes
C(111) C(113) 1.4174(5) 1_555 5_465 yes

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C(124) N(125) C(126) 122.28(3) 1_555 1_555 1_555 yes
C(124) N(125) H(125) 117.70(3) 1_555 1_555 1_555 yes
C(126) N(125) H(125) 119.79(3) 1_555 1_555 1_555 yes
C(122) C(121) C(126) 119.27(3) 1_555 1_555 1_555 yes
C(122) C(121) H(121) 123.74(3) 1_555 1_555 1_555 yes
C(126) C(121) H(121) 116.98(3) 1_555 1_555 1_555 yes
C(121) C(122) C(123) 117.97(3) 1_555 1_555 1_555 yes
C(121) C(122) C(22) 120.70(4) 1_555 1_555 1_555 yes
C(123) C(122) C(22) 121.34(4) 1_555 1_555 1_555 yes
C(122) C(123) C(124) 121.35(3) 1_555 1_555 1_555 yes
C(122) C(123) H(123) 119.84(3) 1_555 1_555 1_555 yes
C(124) C(123) H(123) 118.81(3) 1_555 1_555 1_555 yes
N(125) C(124) C(123) 118.21(3) 1_555 1_555 1_555 yes
N(125) C(124) C(24) 118.90(3) 1_555 1_555 1_555 yes
C(123) C(124) C(24) 122.89(3) 1_555 1_555 1_555 yes
N(125) C(126) C(121) 120.91(3) 1_555 1_555 1_555 yes
N(125) C(126) H(126) 114.85(3) 1_555 1_555 1_555 yes
C(121) C(126) H(126) 124.24(3) 1_555 1_555 1_555 yes
C(122) C(22) H(22A) 113.18(4) 1_555 1_555 1_555 yes
C(122) C(22) H(22B) 113.49(4) 1_555 1_555 1_555 yes
C(122) C(22) H(22C) 110.95(4) 1_555 1_555 1_555 yes
H(22A) C(22) H(22B) 106.16(5) 1_555 1_555 1_555 yes
H(22A) C(22) H(22C) 99.97(5) 1_555 1_555 1_555 yes
H(22B) C(22) H(22C) 112.24(4) 1_555 1_555 1_555 yes
C(124) C(24) H(24A) 111.84(3) 1_555 1_555 1_555 yes
C(124) C(24) H(24B) 110.96(3) 1_555 1_555 1_555 yes
C(124) C(24) H(24C) 109.69(3) 1_555 1_555 1_555 yes
H(24A) C(24) H(24B) 110.05(3) 1_555 1_555 1_555 yes
H(24A) C(24) H(24C) 105.03(4) 1_555 1_555 1_555 yes
H(24B) C(24) H(24C) 109.07(3) 1_555 1_555 1_555 yes
CL(1) C(111) C(112) 118.30(2) 1_555 1_555 1_555 yes
CL(1) C(111) C(113) 118.40(2) 1_555 1_555 5_465 yes
C(112) C(111) C(113) 123.29(3) 1_555 1_555 5_465 yes
O(2) C(112) C(111) 124.26(3) 1_555 1_555 1_555 yes
O(3) C(113) C(111) 124.96(3) 1_555 1_555 5_465 yes

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
C(124) N(125) C(126) C(121) 0.69(4) 1_555 1_555 1_555 1_555 yes
C(126) N(125) C(124) C(123) -0.81(4) 1_555 1_555 1_555 1_555 yes
C(126) N(125) C(124) C(24) 179.50(5) 1_555 1_555 1_555 1_555 yes
C(124) N(125) C(126) H(126) -179.49(5) 1_555 1_555 1_555 1_555 yes
H(125) N(125) C(124) C(123) 173.62(5) 1_555 1_555 1_555 1_555 yes
H(125) N(125) C(124) C(24) -6.07(3) 1_555 1_555 1_555 1_555 yes
H(125) N(125) C(126) C(121) -173.62(6) 1_555 1_555 1_555 1_555 yes
H(125) N(125) C(126) H(126) 6.20(3) 1_555 1_555 1_555 1_555 yes
C(122) C(121) C(126) N(125) 0.03(4) 1_555 1_555 1_555 1_555 yes
C(126) C(121) C(122) C(123) -0.57(4) 1_555 1_555 1_555 1_555 yes
C(126) C(121) C(122) C(22) 179.45(6) 1_555 1_555 1_555 1_555 yes
C(122) C(121) C(126) H(126) -179.78(6) 1_555 1_555 1_555 1_555 yes
H(121) C(121) C(122) C(123) 179.37(6) 1_555 1_555 1_555 1_555 yes
H(121) C(121) C(122) C(22) -0.62(4) 1_555 1_555 1_555 1_555 yes
H(121) C(121) C(126) N(125) -179.91(6) 1_555 1_555 1_555 1_555 yes
H(121) C(121) C(126) H(126) 0.28(3) 1_555 1_555 1_555 1_555 yes
C(121) C(122) C(123) C(124) 0.45(3) 1_555 1_555 1_555 1_555 yes
C(121) C(122) C(123) H(123) -179.17(6) 1_555 1_555 1_555 1_555 yes
C(121) C(122) C(22) H(22A) -21.97(4) 1_555 1_555 1_555 1_555 yes
C(121) C(122) C(22) H(22B) -143.05(6) 1_555 1_555 1_555 1_555 yes
C(121) C(122) C(22) H(22C) 89.49(5) 1_555 1_555 1_555 1_555 yes
C(22) C(122) C(123) C(124) -179.57(6) 1_555 1_555 1_555 1_555 yes
C(22) C(122) C(123) H(123) 0.81(4) 1_555 1_555 1_555 1_555 yes
C(123) C(122) C(22) H(22A) 158.05(6) 1_555 1_555 1_555 1_555 yes
C(123) C(122) C(22) H(22B) 36.97(4) 1_555 1_555 1_555 1_555 yes
C(123) C(122) C(22) H(22C) -90.50(5) 1_555 1_555 1_555 1_555 yes
C(122) C(123) C(124) N(125) 0.23(3) 1_555 1_555 1_555 1_555 yes
C(122) C(123) C(124) C(24) 179.90(6) 1_555 1_555 1_555 1_555 yes
H(123) C(123) C(124) N(125) 179.85(5) 1_555 1_555 1_555 1_555 yes
H(123) C(123) C(124) C(24) -0.48(3) 1_555 1_555 1_555 1_555 yes
N(125) C(124) C(24) H(24A) 13.12(3) 1_555 1_555 1_555 1_555 yes
N(125) C(124) C(24) H(24B) 136.42(5) 1_555 1_555 1_555 1_555 yes
N(125) C(124) C(24) H(24C) -103.00(4) 1_555 1_555 1_555 1_555 yes
C(123) C(124) C(24) H(24A) -166.56(5) 1_555 1_555 1_555 1_555 yes
C(123) C(124) C(24) H(24B) -43.25(4) 1_555 1_555 1_555 1_555 yes
C(123) C(124) C(24) H(24C) 77.33(4) 1_555 1_555 1_555 1_555 yes
CL(1) C(111) C(112) O(2) 0.21(3) 1_555 1_555 1_555 1_555 yes
C(113) C(111) C(112) O(2) 179.20(6) 5_465 1_555 1_555 1_555 yes
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_(2,5)_shelx
_database_code_depnum_ccdc_archive 'CCDC 1478080'
_audit_update_record             
;
2016-05-04 deposited with the CCDC.
2016-06-13 downloaded from the CCDC.
;

_chemical_formula_moiety         
;
C6 H Cl2 O4, C7 H10 N   
;
_chemical_formula_sum            'C13 H11 Cl2 N O4'
_chemical_formula_weight         316.13
_chemical_compound_source        commercial

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14

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

_cell_length_a                   7.7415(2)
_cell_length_b                   11.0538(3)
_cell_length_c                   15.4495(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.5140(10)
_cell_angle_gamma                90
_cell_volume                     1315.94(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    14004
_cell_measurement_theta_min      2.269
_cell_measurement_theta_max      50.621
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.12
_exptl_crystal_density_diffrn    1.596
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.505
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5344
_exptl_absorpt_correction_T_max  0.7498
_exptl_absorpt_process_details   'SADABS, Bruker(2001)'
#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      -0.1033147
_diffrn_orient_matrix_UB_21      -0.682196E-1
_diffrn_orient_matrix_UB_31      -0.389042E-1
_diffrn_orient_matrix_UB_12      0.255648E-1
_diffrn_orient_matrix_UB_22      0.104143E-1
_diffrn_orient_matrix_UB_32      -0.861522E-1
_diffrn_orient_matrix_UB_13      0.296625E-1
_diffrn_orient_matrix_UB_23      -0.578402E-1
_diffrn_orient_matrix_UB_33      0.018102E-2
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_number            74589
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.269
_diffrn_reflns_theta_max         50.621
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_reflns_Friedel_coverage         0
_reflns_number_total             14004
_reflns_number_gt                11372
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
 Scaled and merged with Sortav
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0451P)²+0.0532P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_number_reflns         14004
_refine_ls_number_parameters     225
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0274
_refine_ls_wR_factor_ref         0.0849
_refine_ls_wR_factor_gt          0.0816
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.608
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.061

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.52019(2) 0.22438(2) -0.10921(2) 0.01715(2) Uani 1 1 d . . . . .
Cl2 Cl 0.68286(2) 0.00191(2) 0.26932(2) 0.01853(2) Uani 1 1 d . . . . .
O2 O 0.29138(5) 0.22778(4) 0.03759(3) 0.02618(7) Uani 1 1 d . . . . .
O3 O 0.36145(4) 0.13165(3) 0.19607(2) 0.02108(5) Uani 1 1 d . . . . .
O5 O 0.90416(4) -0.00503(3) 0.12387(2) 0.01928(5) Uani 1 1 d . . . . .
O6 O 0.83558(4) 0.08450(4) -0.03447(2) 0.02127(6) Uani 1 1 d . . . . .
N125 N 0.03679(4) 0.27004(3) 0.16204(2) 0.01624(4) Uani 1 1 d . . . . .
C121 C -0.17492(5) 0.40140(4) 0.09017(3) 0.01702(5) Uani 1 1 d . . . . .
C122 C -0.24354(5) 0.41685(4) 0.17017(3) 0.01894(6) Uani 1 1 d . . . . .
C123 C -0.17131(5) 0.35759(4) 0.24399(3) 0.01907(6) Uani 1 1 d . . . . .
C124 C -0.02767(5) 0.28178(4) 0.23957(3) 0.01652(5) Uani 1 1 d . . . . .
C126 C -0.03213(5) 0.32621(4) 0.08896(3) 0.01708(5) Uani 1 1 d . . . . .
C111 C 0.56077(4) 0.16238(3) -0.00624(2) 0.01356(4) Uani 1 1 d . . . . .
C112 C 0.43366(5) 0.17579(3) 0.05257(2) 0.01533(5) Uani 1 1 d . . . . .
C113 C 0.47267(4) 0.12140(3) 0.14488(2) 0.01468(5) Uani 1 1 d . . . . .
C114 C 0.63806(4) 0.06155(3) 0.16648(2) 0.01394(4) Uani 1 1 d . . . . .
C115 C 0.75309(4) 0.05003(3) 0.10580(2) 0.01362(4) Uani 1 1 d . . . . .
C116 C 0.71801(4) 0.10078(3) 0.01471(2) 0.01384(4) Uani 1 1 d . . . . .
C21 C -0.25117(7) 0.46459(5) 0.00935(3) 0.02384(7) Uani 1 1 d . . . . .
C24 C 0.05645(6) 0.21393(5) 0.31573(3) 0.02251(7) Uani 1 1 d . . . . .
H122 H -0.3345(12) 0.4711(9) 0.1767(6) 0.024(2) Uiso 1 1 d . . . . .
H123 H -0.2206(14) 0.3705(10) 0.2966(7) 0.037(3) Uiso 1 1 d . . . . .
H125 H 0.1230(12) 0.2282(8) 0.1550(6) 0.026(2) Uiso 1 1 d . . . . .
H126 H 0.0194(13) 0.3078(9) 0.0380(7) 0.029(2) Uiso 1 1 d . . . . .
H21A H -0.1735(16) 0.4527(11) -0.0392(8) 0.048(3) Uiso 1 1 d . . . . .
H21B H -0.3623(17) 0.4323(12) -0.0075(8) 0.050(3) Uiso 1 1 d . . . . .
H21C H -0.2607(13) 0.5481(10) 0.0192(6) 0.032(2) Uiso 1 1 d . . . . .
H24A H 0.179(2) 0.2290(14) 0.3290(10) 0.076(5) Uiso 1 1 d . . . . .
H24B H 0.0477(17) 0.1236(12) 0.3102(8) 0.054(3) Uiso 1 1 d . . . . .
H24C H -0.0037(17) 0.2351(12) 0.3643(9) 0.060(4) Uiso 1 1 d . . . . .
H5 H 0.9504(19) -0.0065(12) 0.0791(9) 0.058(4) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   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 C111 1.7330(3) . ?
Cl2 C114 1.7243(3) . ?
O2 C112 1.2442(5) . ?
O3 C113 1.2289(5) . ?
O5 C115 1.3241(4) . ?
O5 H5 0.809(14) . ?
O6 C116 1.2534(4) . ?
N125 C124 1.3474(5) . ?
N125 C126 1.3524(5) . ?
N125 H125 0.828(10) . ?
C121 C126 1.3846(5) . ?
C121 C122 1.4017(6) . ?
C121 C21 1.5013(6) . ?
C122 C123 1.3855(7) . ?
C122 H122 0.937(10) . ?
C123 C124 1.3993(6) . ?
C123 H123 0.941(11) . ?
C124 C24 1.4913(6) . ?
C126 H126 0.939(10) . ?
C111 C116 1.4051(5) . ?
C111 C112 1.4097(5) . ?
C112 C113 1.5506(5) . ?
C113 C114 1.4512(5) . ?
C114 C115 1.3596(5) . ?
C115 C116 1.5152(5) . ?
C21 H21A 1.014(13) . ?
C21 H21B 0.945(13) . ?
C21 H21C 0.940(11) . ?
C24 H24A 0.964(16) . ?
C24 H24B 1.004(13) . ?
C24 H24C 0.950(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
C115 O5 H5 106.5(10) . . ?
C124 N125 C126 123.22(3) . . ?
C124 N125 H125 122.9(7) . . ?
C126 N125 H125 113.9(7) . . ?
C126 C121 C122 117.11(4) . . ?
C126 C121 C21 121.24(4) . . ?
C122 C121 C21 121.64(4) . . ?
C123 C122 C121 120.73(4) . . ?
C123 C122 H122 117.5(6) . . ?
C121 C122 H122 121.7(6) . . ?
C122 C123 C124 120.18(4) . . ?
C122 C123 H123 118.3(7) . . ?
C124 C123 H123 121.5(7) . . ?
N125 C124 C123 117.71(4) . . ?
N125 C124 C24 118.82(4) . . ?
C123 C124 C24 123.48(4) . . ?
N125 C126 C121 121.04(3) . . ?
N125 C126 H126 115.8(6) . . ?
C121 C126 H126 123.0(6) . . ?
C116 C111 C112 123.06(3) . . ?
C116 C111 Cl1 118.66(2) . . ?
C112 C111 Cl1 118.28(3) . . ?
O2 C112 C111 126.09(3) . . ?
O2 C112 C113 116.16(3) . . ?
C111 C112 C113 117.75(3) . . ?
O3 C113 C114 123.45(3) . . ?
O3 C113 C112 118.00(3) . . ?
C114 C113 C112 118.54(3) . . ?
C115 C114 C113 120.40(3) . . ?
C115 C114 Cl2 120.82(3) . . ?
C113 C114 Cl2 118.75(2) . . ?
O5 C115 C114 121.43(3) . . ?
O5 C115 C116 116.22(3) . . ?
C114 C115 C116 122.34(3) . . ?
O6 C116 C111 126.40(3) . . ?
O6 C116 C115 115.73(3) . . ?
C111 C116 C115 117.86(3) . . ?
C121 C21 H21A 110.0(7) . . ?
C121 C21 H21B 109.1(8) . . ?
H21A C21 H21B 109.7(10) . . ?
C121 C21 H21C 110.7(6) . . ?
H21A C21 H21C 107.9(9) . . ?
H21B C21 H21C 109.4(10) . . ?
C124 C24 H24A 115.2(9) . . ?
C124 C24 H24B 114.4(7) . . ?
H24A C24 H24B 104.3(11) . . ?
C124 C24 H24C 106.8(8) . . ?
H24A C24 H24C 109.7(12) . . ?
H24B C24 H24C 106.1(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
C126 C121 C122 C123 -0.77(6) . . . . ?
C21 C121 C122 C123 179.94(4) . . . . ?
C121 C122 C123 C124 0.36(6) . . . . ?
C126 N125 C124 C123 -1.03(6) . . . . ?
C126 N125 C124 C24 178.88(4) . . . . ?
C122 C123 C124 N125 0.53(6) . . . . ?
C122 C123 C124 C24 -179.38(4) . . . . ?
C124 N125 C126 C121 0.63(6) . . . . ?
C122 C121 C126 N125 0.30(6) . . . . ?
C21 C121 C126 N125 179.59(4) . . . . ?
C116 C111 C112 O2 -179.00(4) . . . . ?
Cl1 C111 C112 O2 0.72(6) . . . . ?
C116 C111 C112 C113 1.08(5) . . . . ?
Cl1 C111 C112 C113 -179.19(3) . . . . ?
O2 C112 C113 O3 0.89(6) . . . . ?
C111 C112 C113 O3 -179.19(4) . . . . ?
O2 C112 C113 C114 -178.94(4) . . . . ?
C111 C112 C113 C114 0.99(5) . . . . ?
O3 C113 C114 C115 177.91(4) . . . . ?
C112 C113 C114 C115 -2.28(5) . . . . ?
O3 C113 C114 Cl2 -0.31(6) . . . . ?
C112 C113 C114 Cl2 179.50(3) . . . . ?
C113 C114 C115 O5 -179.48(4) . . . . ?
Cl2 C114 C115 O5 -1.30(5) . . . . ?
C113 C114 C115 C116 1.58(5) . . . . ?
Cl2 C114 C115 C116 179.76(3) . . . . ?
C112 C111 C116 O6 179.26(4) . . . . ?
Cl1 C111 C116 O6 -0.46(6) . . . . ?
C112 C111 C116 C115 -1.82(5) . . . . ?
Cl1 C111 C116 C115 178.45(3) . . . . ?
O5 C115 C116 O6 0.52(5) . . . . ?
C114 C115 C116 O6 179.50(4) . . . . ?
O5 C115 C116 C111 -178.52(3) . . . . ?
C114 C115 C116 C111 0.47(5) . . . . ?

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

data_1_(2,5)_xd
_database_code_depnum_ccdc_archive 'CCDC 1478081'
_audit_update_record             
;
2016-05-04 deposited with the CCDC.
2016-06-13 downloaded from the CCDC.
;

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         
;
C6 H Cl2 O4, C7 H10 N   
;
_chemical_formula_sum            'C13 H11 Cl2 N O4'
_chemical_formula_weight         316.13
_chemical_compound_source        commercial

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14


loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,1/2-Y,1/2+Z

_cell_length_a                   7.7415(2)
_cell_length_b                   11.0538(3)
_cell_length_c                   15.4495(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.5140(10)
_cell_angle_gamma                90
_cell_volume                     1315.94(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    14007
_cell_measurement_theta_min      1
_cell_measurement_theta_max      50.62
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.12
_exptl_crystal_density_diffrn    1.596
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.505
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5344
_exptl_absorpt_correction_T_max  0.7498
_exptl_absorpt_process_details   'SADABS, Bruker(2001)'
#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      -0.1033147
_diffrn_orient_matrix_UB_21      -0.682196E-1
_diffrn_orient_matrix_UB_31      -0.389042E-1
_diffrn_orient_matrix_UB_12      0.255648E-1
_diffrn_orient_matrix_UB_22      0.104143E-1
_diffrn_orient_matrix_UB_32      -0.861522E-1
_diffrn_orient_matrix_UB_13      0.296625E-1
_diffrn_orient_matrix_UB_23      -0.578402E-1
_diffrn_orient_matrix_UB_33      0.018102E-2
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_number            74589
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.27
_diffrn_reflns_theta_max         50.62
_diffrn_reflns_theta_full        50.62
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_reflns_number_total             14007
_reflns_number_gt                11375
_reflns_threshold_expression     >2σ(I)
_diffrn_reflns_reduction_process 
;
 Scaled and merged with Sortav
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
        ?
;
_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
        calc w1 = 1/[s²(Fo)]
;
_refine_ls_extinction_method     'Becker-Coppens type 1 Lorentzian isotropic'
_refine_ls_extinction_expression 
;
        Becker, P.J. & Coppens, P. (1974) Acta Cryst., A30, 129-153.
;
_refine_ls_extinction_coef       0.064(13)
_refine_ls_number_reflns         11797
_refine_ls_number_parameters     543
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.032
_refine_ls_R_factor_gt           0.019
_refine_ls_wR_factor_ref         0.021
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_shift/su_max          0.00001
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.037

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, 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_symmetry_multiplicity
Cl(1) Cl 0.520204(8) 0.224357(6) -0.109199(4) 0.017 Uani 1 4
Cl(2) Cl 0.682872(8) 0.001921(6) 0.269320(4) 0.018 Uani 1 4
O(2) O 0.29125(5) 0.22766(5) 0.03755(3) 0.026 Uani 1 4
O(3) O 0.36158(5) 0.13181(4) 0.19609(2) 0.021 Uani 1 4
O(5) O 0.90424(4) -0.00484(3) 0.12374(2) 0.019 Uani 1 4
O(6) O 0.83561(5) 0.08468(4) -0.03446(2) 0.021 Uani 1 4
N(125) N 0.03692(4) 0.26997(3) 0.162076(19) 0.016 Uani 1 4
C(121) C -0.17492(4) 0.40139(3) 0.09010(2) 0.017 Uani 1 4
C(122) C -0.24372(4) 0.41691(3) 0.17011(2) 0.019 Uani 1 4
C(123) C -0.17114(4) 0.35763(3) 0.24409(2) 0.019 Uani 1 4
C(124) C -0.02767(4) 0.28178(3) 0.239474(19) 0.016 Uani 1 4
C(126) C -0.03201(4) 0.32614(3) 0.088949(19) 0.017 Uani 1 4
C(21) C -0.25120(5) 0.46452(4) 0.00937(2) 0.024 Uani 1 4
C(24) C 0.05637(5) 0.21395(3) 0.31566(2) 0.022 Uani 1 4
C(111) C 0.47270(3) 0.12140(2) 0.144850(16) 0.015 Uani 1 4
C(112) C 0.63803(3) 0.06154(2) 0.166507(15) 0.014 Uani 1 4
C(113) C 0.75323(3) 0.04996(2) 0.105804(16) 0.014 Uani 1 4
C(114) C 0.71810(3) 0.10076(2) 0.014735(16) 0.014 Uani 1 4
C(115) C 0.56069(3) 0.16242(2) -0.006281(16) 0.013 Uani 1 4
C(116) C 0.43366(3) 0.17584(2) 0.052582(17) 0.015 Uani 1 4
H(122) H -0.350292 0.479819 0.177735 0.035 Uani 1 4
H(123) H -0.229121 0.374929 0.304232 0.034 Uani 1 4
H(125) H 0.146452 0.217483 0.153905 0.03 Uani 1 4
H(126) H 0.028743 0.305948 0.030335 0.031 Uani 1 4
H(21A) H -0.168257 0.45021 -0.042944 0.041 Uani 1 4
H(21B) H -0.37992 0.427255 -0.010313 0.042 Uani 1 4
H(21C) H -0.26329 0.561696 0.019985 0.042 Uani 1 4
H(24A) H 0.19385 0.233924 0.331267 0.038 Uani 1 4
H(24B) H 0.049356 0.115415 0.309644 0.039 Uani 1 4
H(24C) H -0.014618 0.236902 0.371167 0.04 Uani 1 4
H(5) H 0.961474 -0.007088 0.069238 0.028 Uani 1 4



#----------------------------------------------------------------------------#
#                   MULTIPOLE PARAMETERS                                     #
#----------------------------------------------------------------------------#

loop_
_atom_rho_multipole_atom_label
_atom_rho_multipole_coeff_Pv
_atom_rho_multipole_coeff_P00
_atom_rho_multipole_coeff_P11
_atom_rho_multipole_coeff_P1-1
_atom_rho_multipole_coeff_P10
_atom_rho_multipole_coeff_P20
_atom_rho_multipole_coeff_P21
_atom_rho_multipole_coeff_P2-1
_atom_rho_multipole_coeff_P22
_atom_rho_multipole_coeff_P2-2
_atom_rho_multipole_coeff_P30
_atom_rho_multipole_coeff_P31
_atom_rho_multipole_coeff_P3-1
_atom_rho_multipole_coeff_P32
_atom_rho_multipole_coeff_P3-2
_atom_rho_multipole_coeff_P33
_atom_rho_multipole_coeff_P3-3
_atom_rho_multipole_coeff_P40
_atom_rho_multipole_coeff_P41
_atom_rho_multipole_coeff_P4-1
_atom_rho_multipole_coeff_P42
_atom_rho_multipole_coeff_P4-2
_atom_rho_multipole_coeff_P43
_atom_rho_multipole_coeff_P4-3
_atom_rho_multipole_coeff_P44
_atom_rho_multipole_coeff_P4-4
_atom_rho_multipole_kappa
_atom_rho_multipole_kappa_prime0
_atom_rho_multipole_kappa_prime1
_atom_rho_multipole_kappa_prime2
_atom_rho_multipole_kappa_prime3
_atom_rho_multipole_kappa_prime4
Cl(1) 7.22(2) 0 -0.040(9) -0.016(9) -0.029(9) -0.136(12) 0.011(10) -0.115(11)
-0.016(10) -0.008(11) 0.063(8) 0.021(7) 0.044(7) 0.007(7) -0.006(8) -0.014(7)
0.007(7) 0.023(11) -0.005(10) 0.040(10) -0.018(10) -0.031(10) -0.002(10)
0.012(10) 0.012(9) -0.012(10) 0.985193 1 1 1 1 1
Cl(2) 7.20(2) 0 0.004(10) -0.009(9) -0.003(9) -0.144(12) -0.027(10) -0.127(11)
-0.032(11) -0.008(11) 0.048(8) 0.006(7) 0.069(7) -0.020(8) -0.002(8) 0.039(7)
-0.004(7) 0.003(11) 0.025(11) 0.045(10) -0.027(10) 0.044(11) -0.002(11)
0.006(10) 0.011(9) 0.010(10) 0.985193 1 1 1 1 1
O(2) 6.061(16) 0 0.048(11) 0.022(8) -0.032(8) -0.012(9) 0.012(10) 0.030(8)
-0.070(10) -0.002(10) -0.045(8) -0.015(8) -0.022(7) 0.075(8) 0.005(8) 0.033(8)
-0.030(8) 0 0 0 0 0 0 0 0 0 0.991401 1.052584 1.052584 1.052584 1.052584
1.052584
O(3) 6.070(14) 0 0.021(9) -0.020(7) -0.041(8) 0.032(8) -0.028(9) -0.033(8)
-0.095(9) -0.004(9) -0.007(7) -0.004(7) 0.022(6) 0.050(7) 0.006(7) 0.015(7)
0.025(7) 0 0 0 0 0 0 0 0 0 0.991401 1.052584 1.052584 1.052584 1.052584
1.052584
O(5) 6.070(17) 0 0.053(8) -0.048(7) -0.044(9) 0.006(9) -0.016(8) -0.001(7)
0.018(8) -0.002(8) 0.069(8) -0.012(7) -0.055(7) 0.035(7) -0.002(7) 0.027(7)
-0.004(7) 0 0 0 0 0 0 0 0 0 0.995111 1.010825 1.010825 1.010825 1.010825
1.010825
O(6) 6.092(14) 0 0.029(9) 0.010(7) -0.048(7) 0.004(9) 0.020(9) -0.030(7)
-0.085(9) 0.001(9) -0.007(7) -0.025(7) 0.014(6) 0.024(7) 0.007(7) 0.034(7)
0.010(7) 0 0 0 0 0 0 0 0 0 0.991401 1.052584 1.052584 1.052584 1.052584
1.052584
N(125) 5.01(2) 0 0.034(10) 0.009(9) -0.017(8) -0.102(8) 0.000(8) -0.010(8)
0.021(9) -0.007(9) -0.010(8) -0.010(8) 0.012(8) 0.006(8) 0.007(8) 0.209(8)
0.018(9) 0 0 0 0 0 0 0 0 0 0.995313 0.990615 0.990615 0.990615 0.990615
0.990615
C(121) 4.02(3) 0 0.016(11) 0.048(11) 0.000(10) -0.197(10) 0.012(9) -0.001(9)
-0.001(10) -0.024(10) 0.001(11) 0.030(10) 0.012(10) 0.000(11) -0.015(11)
0.228(11) 0.003(12) 0 0 0 0 0 0 0 0 0 0.99153 0.989152 0.989152 0.989152
0.989152 0.989152
C(122) 4.05(3) 0 -0.021(11) 0.039(12) 0.007(10) -0.229(10) -0.004(10) -0.006(9)
-0.003(10) -0.005(11) 0.003(11) 0.029(11) 0.000(10) -0.002(11) -0.007(11)
0.257(11) 0.020(12) 0 0 0 0 0 0 0 0 0 0.99153 0.989152 0.989152 0.989152
0.989152 0.989152
C(123) 3.98(3) 0 0.009(11) 0.007(12) -0.039(10) -0.199(10) 0.025(10) 0.015(9)
-0.035(10) 0.004(11) -0.001(11) -0.005(10) 0.058(10) -0.007(11) -0.008(11)
0.222(11) 0.051(12) 0 0 0 0 0 0 0 0 0 0.99153 0.989152 0.989152 0.989152
0.989152 0.989152
C(124) 3.96(3) 0 -0.071(11) 0.024(12) -0.011(9) -0.217(10) 0.004(9) -0.015(10)
-0.028(10) -0.020(10) 0.003(11) 0.013(10) 0.030(10) 0.000(11) -0.009(11)
0.273(12) 0.012(13) 0 0 0 0 0 0 0 0 0 0.99153 0.989152 0.989152 0.989152
0.989152 0.989152
C(126) 4.16(3) 0 0.062(11) -0.051(11) -0.003(10) -0.183(10) 0.006(9) -0.026(9)
0.053(10) 0.053(10) -0.001(11) -0.003(10) 0.025(10) -0.003(10) 0.004(10)
0.227(11) -0.045(12) 0 0 0 0 0 0 0 0 0 0.99153 0.989152 0.989152 0.989152
0.989152 0.989152
C(21) 4.27(4) 0 -0.022(13) 0.034(12) -0.004(12) 0.002(11) 0.020(12) -0.030(11)
-0.005(11) -0.009(11) 0.197(14) -0.024(13) 0.020(12) 0.008(12) 0.055(12)
-0.004(13) -0.209(13) 0 0 0 0 0 0 0 0 0 0.971499 0.919137 0.919137 0.919137
0.919137 0.919137
C(24) 4.66(4) 0 0.106(13) 0.083(12) 0.042(11) 0.038(11) -0.039(11) -0.044(11)
-0.037(11) -0.062(11) 0.162(14) 0.099(12) 0.029(13) -0.087(12) -0.152(12)
0.048(12) -0.204(12) 0 0 0 0 0 0 0 0 0 0.971499 0.919137 0.919137 0.919137
0.919137 0.919137
C(111) 4.12(2) 0 -0.041(9) -0.045(10) 0.000(9) -0.274(9) -0.006(9) -0.002(9)
-0.064(9) 0.061(9) -0.027(10) -0.022(10) 0.003(10) -0.001(10) 0.000(10)
0.270(10) 0.012(11) 0 0 0 0 0 0 0 0 0 0.994369 0.987596 0.987596 0.987596
0.987596 0.987596
C(112) 4.18(2) 0 0.049(10) 0.036(10) 0.010(9) -0.086(9) -0.014(9) 0.003(8)
0.058(9) -0.048(9) -0.002(10) 0.042(10) 0.020(9) 0.002(10) 0.009(10) 0.225(10)
-0.018(11) 0 0 0 0 0 0 0 0 0 0.994369 0.987596 0.987596 0.987596 0.987596
0.987596
C(113) 4.02(2) 0 0.067(10) 0.034(10) 0.001(9) -0.188(9) 0.025(9) 0.003(8)
0.075(9) 0.009(9) -0.003(11) 0.054(10) 0.019(9) -0.010(10) -0.002(10) 0.269(11)
-0.008(11) 0 0 0 0 0 0 0 0 0 0.994369 0.987596 0.987596 0.987596 0.987596
0.987596
C(114) 4.07(2) 0 0.007(10) -0.061(10) 0.015(9) -0.230(9) 0.006(8) 0.002(9)
0.037(9) 0.081(9) -0.012(10) 0.021(10) 0.009(10) 0.002(10) 0.006(10) 0.294(11)
-0.051(11) 0 0 0 0 0 0 0 0 0 0.994369 0.987596 0.987596 0.987596 0.987596
0.987596
C(115) 4.10(2) 0 0.041(10) 0.062(10) 0.015(9) -0.062(9) -0.002(9) 0.007(8)
0.053(9) -0.067(9) 0.017(10) 0.030(10) 0.045(10) 0.022(10) 0.002(10) 0.221(10)
0.026(10) 0 0 0 0 0 0 0 0 0 0.994369 0.987596 0.987596 0.987596 0.987596
0.987596
C(116) 4.07(2) 0 -0.006(10) -0.065(10) -0.003(10) -0.248(10) 0.005(9) 0.001(9)
0.023(9) 0.114(10) 0.014(11) 0.024(10) 0.005(10) 0.007(10) 0.007(10) 0.315(11)
-0.052(11) 0 0 0 0 0 0 0 0 0 0.994369 0.987596 0.987596 0.987596 0.987596
0.987596
H(122) 0.817(10) 0 -0.025(6) -0.028(6) 0.156(8) 0.064(10) 0 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0 1.187768 1.187768 1.187768 1.187768 1.187768 1.187768
H(123) 0.817(10) 0 -0.025(6) -0.028(6) 0.156(8) 0.064(10) 0 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0 1.187768 1.187768 1.187768 1.187768 1.187768 1.187768
H(125) 0.727(15) 0 0.018(10) -0.021(10) 0.176(12) 0.122(17) 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0 0 1.187768 1.187768 1.187768 1.187768 1.187768 1.187768
H(126) 0.817(10) 0 -0.025(6) -0.028(6) 0.156(8) 0.064(10) 0 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0 1.187768 1.187768 1.187768 1.187768 1.187768 1.187768
H(21A) 0.912(12) 0 0.014(8) 0.005(6) 0.132(8) 0.078(10) 0 0 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 1.142425 1.142425 1.142425 1.142425 1.142425 1.142425
H(21B) 0.912(12) 0 0.014(8) 0.005(6) 0.132(8) 0.078(10) 0 0 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 1.142425 1.142425 1.142425 1.142425 1.142425 1.142425
H(21C) 0.912(12) 0 0.014(8) 0.005(6) 0.132(8) 0.078(10) 0 0 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 1.142425 1.142425 1.142425 1.142425 1.142425 1.142425
H(24A) 0.662(12) 0 0.066(7) -0.019(7) 0.108(8) -0.051(11) 0 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0 1.142425 1.142425 1.142425 1.142425 1.142425 1.142425
H(24B) 0.662(12) 0 0.066(7) -0.019(7) 0.108(8) -0.051(11) 0 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0 1.142425 1.142425 1.142425 1.142425 1.142425 1.142425
H(24C) 0.662(12) 0 0.066(7) -0.019(7) 0.108(8) -0.051(11) 0 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0 1.142425 1.142425 1.142425 1.142425 1.142425 1.142425
H(5) 0.725(15) 0 0.003(10) -0.023(10) 0.185(12) 0.074(16) 0 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0 1.175658 1.175658 1.175658 1.175658 1.175658 1.175658

loop_
_atom_local_axes_atom_label
_atom_local_axes_atom0
_atom_local_axes_ax1
_atom_local_axes_atom1
_atom_local_axes_atom2
_atom_local_axes_ax2
CL(1) C(111) Z CL(1) C(112) Y
CL(2) C(114) Z CL(2) C(115) Y
O(2) C(112) Z O(2) H(126) Y
O(3) C(113) Z O(3) H(125) Y
O(5) H(5) Z O(5) C(115) Y
O(6) C(116) Z O(6) H(5) Y
N(125) C(126) X N(125) C(124) Y
C(121) C(126) X C(121) C(122) Y
C(122) C(121) X C(122) C(123) Y
C(123) C(124) X C(123) C(122) Y
C(124) N(125) X C(124) C(123) Y
C(126) C(121) X C(126) N(125) Y
C(21) H(21B) Z C(21) H(21C) Y
C(24) H(24C) Z C(24) H(24A) Y
C(111) C(116) X C(111) C(112) Y
C(112) C(113) X C(112) C(111) Y
C(113) C(112) X C(113) C(114) Y
C(114) C(115) X C(114) C(113) Y
C(115) C(116) X C(115) C(114) Y
C(116) C(115) X C(116) C(111) Y
H(122) C(122) Z H(122) C(123) Y
H(123) C(123) Z H(123) C(122) Y
H(125) N(125) Z H(125) C(126) Y
H(126) C(126) Z H(126) N(125) Y
H(21A) C(21) Z H(21A) H(21B) Y
H(21B) C(21) Z H(21B) H(21C) Y
H(21C) C(21) Z H(21C) H(21B) Y
H(24A) C(24) Z H(24A) H(24B) Y
H(24B) C(24) Z H(24B) H(24C) Y
H(24C) C(24) Z H(24C) H(24B) Y
H(5) O(5) Z H(5) C(115) Y


#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
CL(1) C(115) 1.7319(2) 1_555 1_555 yes
CL(2) C(112) 1.7239(2) 1_555 1_555 yes
O(2) C(116) 1.2443(4) 1_555 1_555 yes
O(3) C(111) 1.2291(4) 1_555 1_555 yes
O(5) C(113) 1.3222(4) 1_555 1_555 yes
O(5) H(5) 0.9888(3) 1_555 1_555 yes
O(6) C(114) 1.2528(4) 1_555 1_555 yes
N(125) C(124) 1.3461(4) 1_555 1_555 yes
N(125) C(126) 1.3531(4) 1_555 1_555 yes
N(125) H(125) 1.0450(3) 1_555 1_555 yes
C(121) C(122) 1.4028(4) 1_555 1_555 yes
C(121) C(126) 1.3856(4) 1_555 1_555 yes
C(121) C(21) 1.4999(5) 1_555 1_555 yes
C(122) C(123) 1.3885(5) 1_555 1_555 yes
C(122) H(122) 1.0940(3) 1_555 1_555 yes
C(123) C(124) 1.3989(4) 1_555 1_555 yes
C(123) H(123) 1.0870(3) 1_555 1_555 yes
C(124) C(24) 1.4912(5) 1_555 1_555 yes
C(126) H(126) 1.0830(3) 1_555 1_555 yes
C(21) H(21A) 1.0910(4) 1_555 1_555 yes
C(21) H(21B) 1.0940(4) 1_555 1_555 yes
C(21) H(21C) 1.0920(4) 1_555 1_555 yes
C(24) H(24A) 1.0910(4) 1_555 1_555 yes
C(24) H(24B) 1.0940(4) 1_555 1_555 yes
C(24) H(24C) 1.0920(4) 1_555 1_555 yes
C(111) C(112) 1.4511(3) 1_555 1_555 yes
C(112) C(113) 1.3609(3) 1_555 1_555 yes
C(113) C(114) 1.5150(3) 1_555 1_555 yes
C(114) C(115) 1.4067(3) 1_555 1_555 yes
C(115) C(116) 1.4099(3) 1_555 1_555 yes

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C(113) O(5) H(5) 107.01(3) 1_555 1_555 1_555 yes
C(124) N(125) C(126) 123.15(3) 1_555 1_555 1_555 yes
C(124) N(125) H(125) 122.42(3) 1_555 1_555 1_555 yes
C(126) N(125) H(125) 114.42(3) 1_555 1_555 1_555 yes
C(122) C(121) C(126) 117.13(3) 1_555 1_555 1_555 yes
C(122) C(121) C(21) 121.56(3) 1_555 1_555 1_555 yes
C(126) C(121) C(21) 121.31(3) 1_555 1_555 1_555 yes
C(121) C(122) C(123) 120.65(3) 1_555 1_555 1_555 yes
C(121) C(122) H(122) 121.79(3) 1_555 1_555 1_555 yes
C(123) C(122) H(122) 117.45(3) 1_555 1_555 1_555 yes
C(122) C(123) C(124) 120.09(3) 1_555 1_555 1_555 yes
C(122) C(123) H(123) 116.93(3) 1_555 1_555 1_555 yes
C(124) C(123) H(123) 122.96(3) 1_555 1_555 1_555 yes
N(125) C(124) C(123) 117.90(3) 1_555 1_555 1_555 yes
N(125) C(124) C(24) 118.77(3) 1_555 1_555 1_555 yes
C(123) C(124) C(24) 123.33(3) 1_555 1_555 1_555 yes
N(125) C(126) C(121) 121.07(3) 1_555 1_555 1_555 yes
N(125) C(126) H(126) 115.81(3) 1_555 1_555 1_555 yes
C(121) C(126) H(126) 123.08(3) 1_555 1_555 1_555 yes
C(121) C(21) H(21A) 109.62(3) 1_555 1_555 1_555 yes
C(121) C(21) H(21B) 109.35(3) 1_555 1_555 1_555 yes
C(121) C(21) H(21C) 111.43(3) 1_555 1_555 1_555 yes
H(21A) C(21) H(21B) 108.95(3) 1_555 1_555 1_555 yes
H(21A) C(21) H(21C) 108.60(3) 1_555 1_555 1_555 yes
H(21B) C(21) H(21C) 108.86(3) 1_555 1_555 1_555 yes
C(124) C(24) H(24A) 114.52(3) 1_555 1_555 1_555 yes
C(124) C(24) H(24B) 114.79(3) 1_555 1_555 1_555 yes
C(124) C(24) H(24C) 106.78(3) 1_555 1_555 1_555 yes
H(24A) C(24) H(24B) 105.05(3) 1_555 1_555 1_555 yes
H(24A) C(24) H(24C) 109.47(3) 1_555 1_555 1_555 yes
H(24B) C(24) H(24C) 105.87(3) 1_555 1_555 1_555 yes
O(3) C(111) C(112) 123.40(3) 1_555 1_555 1_555 yes
CL(2) C(112) C(111) 118.805(18) 1_555 1_555 1_555 yes
CL(2) C(112) C(113) 120.781(19) 1_555 1_555 1_555 yes
C(111) C(112) C(113) 120.39(2) 1_555 1_555 1_555 yes
O(5) C(113) C(112) 121.56(2) 1_555 1_555 1_555 yes
O(5) C(113) C(114) 116.15(2) 1_555 1_555 1_555 yes
C(112) C(113) C(114) 122.28(2) 1_555 1_555 1_555 yes
O(6) C(114) C(113) 115.77(2) 1_555 1_555 1_555 yes
O(6) C(114) C(115) 126.31(3) 1_555 1_555 1_555 yes
C(113) C(114) C(115) 117.91(2) 1_555 1_555 1_555 yes
CL(1) C(115) C(114) 118.670(18) 1_555 1_555 1_555 yes
CL(1) C(115) C(116) 118.339(19) 1_555 1_555 1_555 yes
C(114) C(115) C(116) 122.99(2) 1_555 1_555 1_555 yes
O(2) C(116) C(115) 126.05(3) 1_555 1_555 1_555 yes

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
H(5) O(5) C(113) C(112) 176.27(4) 1_555 1_555 1_555 1_555 yes
H(5) O(5) C(113) C(114) -4.85(2) 1_555 1_555 1_555 1_555 yes
C(124) N(125) C(126) C(121) 0.64(3) 1_555 1_555 1_555 1_555 yes
C(126) N(125) C(124) C(123) -1.13(3) 1_555 1_555 1_555 1_555 yes
C(126) N(125) C(124) C(24) 178.87(5) 1_555 1_555 1_555 1_555 yes
C(124) N(125) C(126) H(126) -177.39(4) 1_555 1_555 1_555 1_555 yes
H(125) N(125) C(124) C(123) 177.75(5) 1_555 1_555 1_555 1_555 yes
H(125) N(125) C(124) C(24) -2.25(3) 1_555 1_555 1_555 1_555 yes
H(125) N(125) C(126) C(121) -178.33(4) 1_555 1_555 1_555 1_555 yes
H(125) N(125) C(126) H(126) 3.65(2) 1_555 1_555 1_555 1_555 yes
C(122) C(121) C(126) N(125) 0.29(3) 1_555 1_555 1_555 1_555 yes
C(126) C(121) C(122) C(123) -0.67(3) 1_555 1_555 1_555 1_555 yes
C(126) C(121) C(122) H(122) 175.44(5) 1_555 1_555 1_555 1_555 yes
C(122) C(121) C(126) H(126) 178.17(5) 1_555 1_555 1_555 1_555 yes
C(21) C(121) C(122) C(123) -179.99(5) 1_555 1_555 1_555 1_555 yes
C(21) C(121) C(122) H(122) -3.88(3) 1_555 1_555 1_555 1_555 yes
C(122) C(121) C(21) H(21A) 172.17(5) 1_555 1_555 1_555 1_555 yes
C(122) C(121) C(21) H(21B) -68.46(3) 1_555 1_555 1_555 1_555 yes
C(122) C(121) C(21) H(21C) 51.93(3) 1_555 1_555 1_555 1_555 yes
C(21) C(121) C(126) N(125) 179.61(5) 1_555 1_555 1_555 1_555 yes
C(21) C(121) C(126) H(126) -2.52(3) 1_555 1_555 1_555 1_555 yes
C(126) C(121) C(21) H(21A) -7.12(3) 1_555 1_555 1_555 1_555 yes
C(126) C(121) C(21) H(21B) 112.26(4) 1_555 1_555 1_555 1_555 yes
C(126) C(121) C(21) H(21C) -127.36(4) 1_555 1_555 1_555 1_555 yes
C(121) C(122) C(123) C(124) 0.18(3) 1_555 1_555 1_555 1_555 yes
C(121) C(122) C(123) H(123) 178.86(5) 1_555 1_555 1_555 1_555 yes
H(122) C(122) C(123) C(124) -176.09(5) 1_555 1_555 1_555 1_555 yes
H(122) C(122) C(123) H(123) 2.59(3) 1_555 1_555 1_555 1_555 yes
C(122) C(123) C(124) N(125) 0.71(3) 1_555 1_555 1_555 1_555 yes
C(122) C(123) C(124) C(24) -179.29(5) 1_555 1_555 1_555 1_555 yes
H(123) C(123) C(124) N(125) -177.89(5) 1_555 1_555 1_555 1_555 yes
H(123) C(123) C(124) C(24) 2.11(3) 1_555 1_555 1_555 1_555 yes
N(125) C(124) C(24) H(24A) 58.09(3) 1_555 1_555 1_555 1_555 yes
N(125) C(124) C(24) H(24B) -63.58(3) 1_555 1_555 1_555 1_555 yes
N(125) C(124) C(24) H(24C) 179.43(4) 1_555 1_555 1_555 1_555 yes
C(123) C(124) C(24) H(24A) -121.91(4) 1_555 1_555 1_555 1_555 yes
C(123) C(124) C(24) H(24B) 116.42(4) 1_555 1_555 1_555 1_555 yes
C(123) C(124) C(24) H(24C) -0.57(3) 1_555 1_555 1_555 1_555 yes
O(3) C(111) C(112) CL(2) -0.21(3) 1_555 1_555 1_555 1_555 yes
O(3) C(111) C(112) C(113) 178.01(4) 1_555 1_555 1_555 1_555 yes
CL(2) C(112) C(113) O(5) -1.39(2) 1_555 1_555 1_555 1_555 yes
CL(2) C(112) C(113) C(114) 179.79(3) 1_555 1_555 1_555 1_555 yes
C(111) C(112) C(113) O(5) -179.58(4) 1_555 1_555 1_555 1_555 yes
C(111) C(112) C(113) C(114) 1.61(2) 1_555 1_555 1_555 1_555 yes
O(5) C(113) C(114) O(6) 0.53(3) 1_555 1_555 1_555 1_555 yes
O(5) C(113) C(114) C(115) -178.44(4) 1_555 1_555 1_555 1_555 yes
C(112) C(113) C(114) O(6) 179.41(4) 1_555 1_555 1_555 1_555 yes
C(112) C(113) C(114) C(115) 0.43(2) 1_555 1_555 1_555 1_555 yes
O(6) C(114) C(115) CL(1) -0.38(3) 1_555 1_555 1_555 1_555 yes
O(6) C(114) C(115) C(116) 179.39(5) 1_555 1_555 1_555 1_555 yes
C(113) C(114) C(115) CL(1) 178.47(3) 1_555 1_555 1_555 1_555 yes
C(113) C(114) C(115) C(116) -1.76(2) 1_555 1_555 1_555 1_555 yes
CL(1) C(115) C(116) O(2) 0.87(3) 1_555 1_555 1_555 1_555 yes
C(114) C(115) C(116) O(2) -178.90(5) 1_555 1_555 1_555 1_555 yes
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_(2,5)_neutron
_database_code_depnum_ccdc_archive 'CCDC 1478082'
_audit_update_record             
;
2016-05-04 deposited with the CCDC.
2016-06-13 downloaded from the CCDC.
;

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         
;
C6 H Cl2 O4, C7 H10 N 
;
_chemical_formula_sum            'C13 H11 Cl2 N O4'
_chemical_formula_weight         316.13
_chemical_compound_source        commercial

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.7415(2)
_cell_length_b                   11.0538(3)
_cell_length_c                   15.4495(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.5140(10)
_cell_angle_gamma                90
_cell_volume                     1315.94(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7915
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      61.7
_cell_measurement_wavelength     0.9484

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#
_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          4
_exptl_crystal_size_mid          3
_exptl_crystal_size_min          2
_exptl_crystal_density_diffrn    1.596
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             388
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.1421
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.9484
_diffrn_radiation_probe          neutron
_diffrn_radiation_type           neutron
_diffrn_radiation_source         'nuclear reactor'

_diffrn_radiation_monochromator  Cu(220)
_diffrn_measurement_device_type  '4-circles Eulerian cradle'
_diffrn_measurement_method       'omega scans'
_diffrn_detector                 'multiwire proportional chamber'
_diffrn_detector_area_resol_mean 0.52
_diffrn_detector_details         
;
ILL cylindrically shaped large-area position sensitive detector 
with 120 by 30 deg detection angle (resolution: 0.4 by 0.64 pixels/mm)
;

_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.046
_diffrn_reflns_number            7915
_diffrn_reflns_limit_h_min       -2
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.028
_diffrn_reflns_theta_max         61.703
_diffrn_reflns_theta_full        34.683
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.897
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.897
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.897
_reflns_number_total             7915
_reflns_number_gt                6452
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'ILL-MAD software'
_computing_cell_refinement       'Dirax (Duisenberg, 1992)'
_computing_data_reduction        'PFIND, RETREAT (Wilkinson et al.,1988)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_atom_sites_solution_hydrogens   difmap

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
goodness of fit S are based on F², conventional R-factors R are based 
on F, with F set to zero for negative F². The threshold expression of 
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
not relevant to the choice of reflections for refinement.  R-factors based 
on F² are statistically about twice as large as those based on F, and R- 
factors based on ALL data will be even larger. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0325P)²+1.0848P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0062(4)
_refine_ls_number_reflns         7915
_refine_ls_number_parameters     309
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0378
_refine_ls_wR_factor_ref         0.0941
_refine_ls_wR_factor_gt          0.0891
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_restrained_S_all      1.103
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.775
_refine_diff_density_min         -1.039
_refine_diff_density_rms         0.195

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_length_neutron
_atom_type_scat_source
C C 0.0000 0.0000 6.646 'Neutron Data Booklet Table 1.1-8'
H H 0.0000 0.0000 -3.739 'Neutron Data Booklet Table 1.1-8'
N N 0.0000 0.0000 9.36 'Neutron Data Booklet Table 1.1-8'
O O 0.0000 0.0000 5.803 'Neutron Data Booklet Table 1.1-8'
Cl Cl 0.0000 0.0000 9.577 'Neutron Data Booklet Table 1.1-8'

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 0.52014(5) 0.22435(3) -0.10923(2) 0.01736(6) Uani 1 1 d . . . . .
Cl2 Cl 0.68284(5) 0.00202(4) 0.26932(2) 0.01877(7) Uani 1 1 d . . . . .
O2 O 0.29160(10) 0.22766(8) 0.03762(5) 0.02627(14) Uani 1 1 d . . . . .
O3 O 0.36170(9) 0.13176(7) 0.19599(4) 0.02141(11) Uani 1 1 d . . . . .
O5 O 0.90394(9) -0.00501(6) 0.12366(4) 0.01956(10) Uani 1 1 d . . . . .
O6 O 0.83542(9) 0.08460(7) -0.03450(4) 0.02155(11) Uani 1 1 d . . . . .
N125 N 0.03672(5) 0.27005(3) 0.16192(2) 0.01701(6) Uani 1 1 d . . . . .
C121 C -0.17499(7) 0.40154(5) 0.08999(3) 0.01737(8) Uani 1 1 d . . . . .
C122 C -0.24376(7) 0.41699(5) 0.17005(4) 0.01932(9) Uani 1 1 d . . . . .
C123 C -0.17115(8) 0.35767(5) 0.24404(3) 0.01911(9) Uani 1 1 d . . . . .
C124 C -0.02778(7) 0.28193(5) 0.23950(3) 0.01688(8) Uani 1 1 d . . . . .
C126 C -0.03215(7) 0.32623(5) 0.08880(3) 0.01746(8) Uani 1 1 d . . . . .
C111 C 0.56073(7) 0.16251(4) -0.00635(3) 0.01393(7) Uani 1 1 d . . . . .
C112 C 0.43350(7) 0.17586(4) 0.05254(3) 0.01578(8) Uani 1 1 d . . . . .
C113 C 0.47256(7) 0.12138(4) 0.14490(3) 0.01492(8) Uani 1 1 d . . . . .
C114 C 0.63806(7) 0.06154(4) 0.16657(3) 0.01415(7) Uani 1 1 d . . . . .
C115 C 0.75319(7) 0.04993(4) 0.10582(3) 0.01398(7) Uani 1 1 d . . . . .
C116 C 0.71812(7) 0.10083(4) 0.01467(3) 0.01434(7) Uani 1 1 d . . . . .
C21 C -0.25134(9) 0.46463(6) 0.00930(4) 0.02398(10) Uani 1 1 d . . . . .
C24 C 0.05619(9) 0.21403(6) 0.31570(4) 0.02243(10) Uani 1 1 d . . . . .
H5 H 0.96839(19) -0.01046(15) 0.07159(8) 0.0340(3) Uani 1 1 d . . . . .
H122 H -0.3539(2) 0.47785(16) 0.17491(11) 0.0392(3) Uani 1 1 d . . . . .
H123 H -0.2220(2) 0.37058(16) 0.30659(9) 0.0382(3) Uani 1 1 d . . . . .
H125 H 0.14831(18) 0.21822(13) 0.15730(9) 0.0316(2) Uani 1 1 d . . . . .
H126 H 0.0331(2) 0.30730(15) 0.03119(8) 0.0349(3) Uani 1 1 d . . . . .
H21A H -0.1720(3) 0.4509(2) -0.04453(11) 0.0551(5) Uani 1 1 d . . . . .
H21B H -0.3807(3) 0.4290(2) -0.01115(15) 0.0520(5) Uani 1 1 d . . . . .
H21C H -0.2649(3) 0.56171(15) 0.01974(13) 0.0463(4) Uani 1 1 d . . . . .
H24A H 0.1807(13) 0.2479(9) 0.3343(7) 0.072(3) Uani 0.53(2) 1 d . . P A 1
H24B H 0.0661(17) 0.1219(6) 0.3005(5) 0.072(3) Uani 0.53(2) 1 d . . P A 1
H24C H -0.0198(10) 0.2245(11) 0.3685(5) 0.066(3) Uani 0.53(2) 1 d . . P A 1
H24D H 0.1936(11) 0.214(2) 0.3186(8) 0.093(5) Uani 0.47(2) 1 d . . P A 2
H24E H 0.017(2) 0.1239(8) 0.3135(10) 0.090(4) Uani 0.47(2) 1 d . . P A 2
H24F H 0.027(3) 0.2523(12) 0.3743(5) 0.094(5) Uani 0.47(2) 1 d . . P A 2



#----------------------------------------------------------------------------#
#                   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 C111 1.7310(5) . ?
Cl2 C114 1.7226(5) . ?
O2 C112 1.2406(8) . ?
O3 C113 1.2259(8) . ?
O5 C115 1.3209(8) . ?
O5 H5 0.9883(14) . ?
O6 C116 1.2515(8) . ?
N125 C124 1.3484(6) . ?
N125 C126 1.3529(6) . ?
N125 H125 1.0448(14) . ?
C121 C126 1.3857(8) . ?
C121 C122 1.4032(7) . ?
C121 C21 1.4994(8) . ?
C122 C123 1.3890(8) . ?
C122 H122 1.0941(15) . ?
C123 C124 1.3974(8) . ?
C123 H123 1.0873(14) . ?
C124 C24 1.4916(8) . ?
C126 H126 1.0850(13) . ?
C111 C116 1.4067(7) . ?
C111 C112 1.4114(7) . ?
C112 C113 1.5516(6) . ?
C113 C114 1.4522(7) . ?
C114 C115 1.3611(6) . ?
C115 C116 1.5165(6) . ?
C21 H21A 1.0910(19) . ?
C21 H21B 1.0938(19) . ?
C21 H21C 1.0918(18) . ?
C24 H24A 1.048(7) . ?
C24 H24B 1.050(6) . ?
C24 H24C 1.057(6) . ?
C24 H24D 1.060(9) . ?
C24 H24E 1.040(7) . ?
C24 H24F 1.044(7) . ?

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
C115 O5 H5 111.30(10) . . ?
C124 N125 C126 123.21(4) . . ?
C124 N125 H125 119.57(9) . . ?
C126 N125 H125 117.18(9) . . ?
C126 C121 C122 117.11(5) . . ?
C126 C121 C21 121.31(5) . . ?
C122 C121 C21 121.57(5) . . ?
C123 C122 C121 120.67(5) . . ?
C123 C122 H122 119.35(10) . . ?
C121 C122 H122 119.97(10) . . ?
C122 C123 C124 120.14(5) . . ?
C122 C123 H123 121.14(11) . . ?
C124 C123 H123 118.70(11) . . ?
N125 C124 C123 117.82(5) . . ?
N125 C124 C24 118.82(5) . . ?
C123 C124 C24 123.36(5) . . ?
N125 C126 C121 121.04(4) . . ?
N125 C126 H126 114.79(9) . . ?
C121 C126 H126 124.17(9) . . ?
C116 C111 C112 122.99(4) . . ?
C116 C111 Cl1 118.70(4) . . ?
C112 C111 Cl1 118.31(4) . . ?
O2 C112 C111 126.07(5) . . ?
O2 C112 C113 116.16(5) . . ?
C111 C112 C113 117.77(4) . . ?
O3 C113 C114 123.43(5) . . ?
O3 C113 C112 117.98(5) . . ?
C114 C113 C112 118.59(4) . . ?
C115 C114 C113 120.38(4) . . ?
C115 C114 Cl2 120.82(4) . . ?
C113 C114 Cl2 118.77(4) . . ?
O5 C115 C114 121.56(4) . . ?
O5 C115 C116 116.11(4) . . ?
C114 C115 C116 122.32(4) . . ?
O6 C116 C111 126.32(5) . . ?
O6 C116 C115 115.77(5) . . ?
C111 C116 C115 117.91(4) . . ?
C121 C21 H21A 111.29(12) . . ?
C121 C21 H21B 110.45(12) . . ?
H21A C21 H21B 107.3(2) . . ?
C121 C21 H21C 111.72(11) . . ?
H21A C21 H21C 108.60(19) . . ?
H21B C21 H21C 107.34(18) . . ?
C124 C24 H24A 110.8(5) . . ?
C124 C24 H24B 110.4(4) . . ?
H24A C24 H24B 108.8(8) . . ?
C124 C24 H24C 108.7(5) . . ?
H24A C24 H24C 108.4(8) . . ?
H24B C24 H24C 109.7(8) . . ?
C124 C24 H24D 113.2(6) . . ?
C124 C24 H24E 110.7(6) . . ?
H24D C24 H24E 106.5(11) . . ?
C124 C24 H24F 111.5(6) . . ?
H24D C24 H24F 105.3(11) . . ?
H24E C24 H24F 109.3(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
C126 C121 C122 C123 -0.63(8) . . . . ?
C21 C121 C122 C123 179.97(5) . . . . ?
C121 C122 C123 C124 0.21(8) . . . . ?
C126 N125 C124 C123 -1.01(7) . . . . ?
C126 N125 C124 C24 178.85(5) . . . . ?
C122 C123 C124 N125 0.59(8) . . . . ?
C122 C123 C124 C24 -179.26(5) . . . . ?
C124 N125 C126 C121 0.60(8) . . . . ?
C122 C121 C126 N125 0.25(8) . . . . ?
C21 C121 C126 N125 179.65(5) . . . . ?
C116 C111 C112 O2 -179.00(7) . . . . ?
Cl1 C111 C112 O2 0.67(9) . . . . ?
C116 C111 C112 C113 1.08(7) . . . . ?
Cl1 C111 C112 C113 -179.25(4) . . . . ?
O2 C112 C113 O3 0.76(9) . . . . ?
C111 C112 C113 O3 -179.32(6) . . . . ?
O2 C112 C113 C114 -178.92(6) . . . . ?
C111 C112 C113 C114 1.01(7) . . . . ?
O3 C113 C114 C115 177.98(6) . . . . ?
C112 C113 C114 C115 -2.36(7) . . . . ?
O3 C113 C114 Cl2 -0.20(8) . . . . ?
C112 C113 C114 Cl2 179.46(4) . . . . ?
C113 C114 C115 O5 -179.42(5) . . . . ?
Cl2 C114 C115 O5 -1.28(8) . . . . ?
C113 C114 C115 C116 1.71(7) . . . . ?
Cl2 C114 C115 C116 179.85(4) . . . . ?
C112 C111 C116 O6 179.22(6) . . . . ?
Cl1 C111 C116 O6 -0.44(8) . . . . ?
C112 C111 C116 C115 -1.79(7) . . . . ?
Cl1 C111 C116 C115 178.55(4) . . . . ?
O5 C115 C116 O6 0.54(8) . . . . ?
C114 C115 C116 O6 179.47(6) . . . . ?
O5 C115 C116 C111 -178.55(5) . . . . ?
C114 C115 C116 C111 0.37(7) . . . . ?

####################################################################### 
# 
# 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_2_(2,5)_shelx
_database_code_depnum_ccdc_archive 'CCDC 1478083'
_audit_update_record             
;
2016-05-04 deposited with the CCDC.
2016-06-13 downloaded from the CCDC.
;

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         
;
C6 Cl2 O4, 2(C7 H10 N)  
;
_chemical_formula_sum            'C20 H20 Cl2 N2 O4'
_chemical_formula_weight         423.28
_chemical_compound_source        commercial
#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14

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

_cell_length_a                   8.0870(3)
_cell_length_b                   11.4214(5)
_cell_length_c                   10.3253(4)
_cell_angle_alpha                90
_cell_angle_beta                 100.451(2)
_cell_angle_gamma                90
_cell_volume                     937.87(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    10032
_cell_measurement_theta_min      2.561
_cell_measurement_theta_max      50.638
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.21
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             440
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.377
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5300
_exptl_absorpt_correction_T_max  0.7494
_exptl_absorpt_process_details   'SADABS, Bruker(2001)'
#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      -0.1016472
_diffrn_orient_matrix_UB_21      0.362709E-1
_diffrn_orient_matrix_UB_31      0.644694E-1
_diffrn_orient_matrix_UB_12      -0.514523E-1
_diffrn_orient_matrix_UB_22      -0.381233E-1
_diffrn_orient_matrix_UB_32      -0.596751E-1
_diffrn_orient_matrix_UB_13      -0.118218E-1
_diffrn_orient_matrix_UB_23      -0.775134E-1
_diffrn_orient_matrix_UB_33      0.597121E-1
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_number            10037
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.56
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         50.638
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.991
_reflns_Friedel_coverage         0
_reflns_number_total             10032
_reflns_number_gt                8713
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
 Scaled and merged with Sortav
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0514P)²+0.0260P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_number_reflns         10032
_refine_ls_number_parameters     167
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0251
_refine_ls_wR_factor_ref         0.0839
_refine_ls_wR_factor_gt          0.0816
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.584
_refine_diff_density_min         -0.415
_refine_diff_density_rms         0.058

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 1.07063(2) 0.21399(2) 1.32016(2) 0.01637(2) Uani 1 1 d . . . . .
O2 O 0.83230(3) 0.01631(3) 1.24728(2) 0.01871(4) Uani 1 1 d . . . . .
O3 O 0.75484(3) -0.15478(3) 1.40549(3) 0.01880(4) Uani 1 1 d . . . . .
N125 N 0.53364(3) -0.07296(2) 1.14707(2) 0.01312(3) Uani 1 1 d . . . . .
C121 C 0.35354(4) -0.19612(3) 0.99753(3) 0.01348(4) Uani 1 1 d . . . . .
C122 C 0.21631(4) -0.13167(3) 1.02557(3) 0.01527(4) Uani 1 1 d . . . . .
C123 C 0.24135(4) -0.03917(3) 1.11428(3) 0.01644(4) Uani 1 1 d . . . . .
C124 C 0.40447(4) -0.00989(3) 1.17582(3) 0.01465(4) Uani 1 1 d . . . . .
C126 C 0.51263(3) -0.16318(2) 1.06085(3) 0.01317(4) Uani 1 1 d . . . . .
C21 C 0.33062(5) -0.29641(3) 0.90204(4) 0.01890(5) Uani 1 1 d . . . . .
C24 C 0.44336(5) 0.08824(3) 1.27260(4) 0.02131(6) Uani 1 1 d . . . . .
C111 C 1.03188(3) 0.09652(3) 1.41815(3) 0.01334(4) Uani 1 1 d . . . . .
C112 C 0.91181(3) 0.01373(3) 1.36422(3) 0.01318(4) Uani 1 1 d . . . . .
C113 C 0.87115(3) -0.08770(3) 1.45272(3) 0.01308(4) Uani 1 1 d . . . . .
H122 H 0.1031(12) -0.1592(8) 0.9825(9) 0.0243(19) Uiso 1 1 d . . . . .
H123 H 0.1487(13) 0.0086(9) 1.1358(10) 0.032(2) Uiso 1 1 d . . . . .
H125 H 0.6443(11) -0.0497(8) 1.1898(9) 0.0255(19) Uiso 1 1 d . . . . .
H126 H 0.6133(12) -0.2028(7) 1.0434(9) 0.023(2) Uiso 1 1 d . . . . .
H21A H 0.4428(12) -0.3319(9) 0.8893(10) 0.033(2) Uiso 1 1 d . . . . .
H21B H 0.2645(13) -0.3565(9) 0.9369(10) 0.038(3) Uiso 1 1 d . . . . .
H21C H 0.2766(14) -0.2684(9) 0.8165(10) 0.035(2) Uiso 1 1 d . . . . .
H24A H 0.5622(13) 0.1020(11) 1.2929(10) 0.041(3) Uiso 1 1 d . . . . .
H24B H 0.4077(15) 0.0741(10) 1.3548(11) 0.044(3) Uiso 1 1 d . . . . .
H24C H 0.3971(12) 0.1610(9) 1.2376(10) 0.030(2) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   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 C111 1.7427(3) . ?
O2 C112 1.2612(3) . ?
O3 C113 1.2422(4) . ?
N125 C124 1.3456(4) . ?
N125 C126 1.3522(4) . ?
N125 H125 0.961(9) . ?
C121 C126 1.3853(4) . ?
C121 C122 1.4049(4) . ?
C121 C21 1.5008(4) . ?
C122 C123 1.3889(5) . ?
C122 H122 0.994(9) . ?
C123 C124 1.3970(4) . ?
C123 H123 0.984(10) . ?
C124 C24 1.4965(5) . ?
C126 H126 0.977(9) . ?
C21 H21A 1.024(10) . ?
C21 H21B 0.978(10) . ?
C21 H21C 0.967(10) . ?
C24 H24A 0.959(11) . ?
C24 H24B 0.958(11) . ?
C24 H24C 0.955(10) . ?
C111 C112 1.3968(4) . ?
C111 C113 1.4225(4) 3_758 ?
C112 C113 1.5472(4) . ?
C113 C111 1.4225(4) 3_758 ?

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
C124 N125 C126 122.91(3) . . ?
C124 N125 H125 116.5(5) . . ?
C126 N125 H125 120.6(5) . . ?
C126 C121 C122 117.47(3) . . ?
C126 C121 C21 120.71(3) . . ?
C122 C121 C21 121.82(3) . . ?
C123 C122 C121 120.55(3) . . ?
C123 C122 H122 123.2(5) . . ?
C121 C122 H122 116.1(5) . . ?
C122 C123 C124 119.65(3) . . ?
C122 C123 H123 123.0(6) . . ?
C124 C123 H123 117.4(6) . . ?
N125 C124 C123 118.57(3) . . ?
N125 C124 C24 118.08(3) . . ?
C123 C124 C24 123.35(3) . . ?
N125 C126 C121 120.84(3) . . ?
N125 C126 H126 117.8(5) . . ?
C121 C126 H126 121.4(5) . . ?
C121 C21 H21A 112.3(6) . . ?
C121 C21 H21B 107.8(6) . . ?
H21A C21 H21B 109.0(8) . . ?
C121 C21 H21C 109.2(6) . . ?
H21A C21 H21C 106.1(9) . . ?
H21B C21 H21C 112.5(9) . . ?
C124 C24 H24A 110.5(7) . . ?
C124 C24 H24B 113.8(7) . . ?
H24A C24 H24B 106.5(10) . . ?
C124 C24 H24C 112.2(6) . . ?
H24A C24 H24C 104.4(9) . . ?
H24B C24 H24C 108.8(9) . . ?
C112 C111 C113 123.43(3) . 3_758 ?
C112 C111 Cl1 118.36(2) . . ?
C113 C111 Cl1 118.17(2) 3_758 . ?
O2 C112 C111 124.24(3) . . ?
O2 C112 C113 117.18(2) . . ?
C111 C112 C113 118.57(2) . . ?
O3 C113 C111 125.01(3) . 3_758 ?
O3 C113 C112 117.18(2) . . ?
C111 C113 C112 117.81(2) 3_758 . ?

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
C126 C121 C122 C123 -0.40(4) . . . . ?
C21 C121 C122 C123 -179.92(3) . . . . ?
C121 C122 C123 C124 0.16(5) . . . . ?
C126 N125 C124 C123 0.26(4) . . . . ?
C126 N125 C124 C24 -179.82(3) . . . . ?
C122 C123 C124 N125 -0.08(5) . . . . ?
C122 C123 C124 C24 180.00(3) . . . . ?
C124 N125 C126 C121 -0.51(4) . . . . ?
C122 C121 C126 N125 0.56(4) . . . . ?
C21 C121 C126 N125 -179.90(3) . . . . ?
C113 C111 C112 O2 -175.39(3) 3_758 . . . ?
Cl1 C111 C112 O2 2.16(4) . . . . ?
C113 C111 C112 C113 5.16(5) 3_758 . . . ?
Cl1 C111 C112 C113 -177.30(2) . . . . ?
O2 C112 C113 O3 -4.95(4) . . . . ?
C111 C112 C113 O3 174.55(3) . . . . ?
O2 C112 C113 C111 175.64(3) . . . 3_758 ?
C111 C112 C113 C111 -4.87(4) . . . 3_758 ?

####################################################################### 
# 
# 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_2_(2,5)_xd
_database_code_depnum_ccdc_archive 'CCDC 1478084'
_audit_update_record             
;
2016-05-04 deposited with the CCDC.
2016-06-13 downloaded from the CCDC.
;

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         
;
C6 Cl2 O4, 2(C7 H10 N) 
;
_chemical_formula_sum            'C20 H20 Cl2 N2 O4'
_chemical_formula_weight         423.28
_chemical_compound_source        commercial

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14

loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,1/2-Y,1/2+Z

_cell_length_a                   8.0870(3)
_cell_length_b                   11.4214(5)
_cell_length_c                   10.3253(4)
_cell_angle_alpha                90
_cell_angle_beta                 100.451(2)
_cell_angle_gamma                90
_cell_volume                     937.87(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    10037
_cell_measurement_theta_min      1
_cell_measurement_theta_max      50.64
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.21
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             440
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.377
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5300
_exptl_absorpt_correction_T_max  0.7494
_exptl_absorpt_process_details   'SADABS, Bruker(2001)'
#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      -0.1016472
_diffrn_orient_matrix_UB_21      0.362709E-1
_diffrn_orient_matrix_UB_31      0.644694E-1
_diffrn_orient_matrix_UB_12      -0.514523E-1
_diffrn_orient_matrix_UB_22      -0.381233E-1
_diffrn_orient_matrix_UB_32      -0.596751E-1
_diffrn_orient_matrix_UB_13      -0.118218E-1
_diffrn_orient_matrix_UB_23      -0.775134E-1
_diffrn_orient_matrix_UB_33      0.597121E-1
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_number            10037
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.56
_diffrn_reflns_theta_max         50.64
_diffrn_reflns_theta_full        50.64
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_reflns_number_total             10037
_reflns_number_gt                8718
_reflns_threshold_expression     >2σ(I)
_diffrn_reflns_reduction_process 
;
 Scaled and merged with Sortav
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
        ?
;
_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
        calc w1 = 1/[s²(Fo)]
;
_refine_ls_extinction_method     'Becker-Coppens type 1 Lorentzian isotropic'
_refine_ls_extinction_expression 
;
        Becker, P.J. & Coppens, P. (1974) Acta Cryst., A30, 129-153.
;
_refine_ls_extinction_coef       0.028(15)
_refine_ls_number_reflns         8919
_refine_ls_number_parameters     379
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.023
_refine_ls_R_factor_gt           0.015
_refine_ls_wR_factor_ref         0.019
_refine_ls_goodness_of_fit_ref   1.171
_refine_ls_shift/su_max          0.00006
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.029

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, 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_symmetry_multiplicity
Cl(1) Cl 1.070650(6) 0.213988(4) 1.320153(4) 0.016 Uani 1 4
O(2) O 0.83238(3) 0.01626(2) 1.24730(2) 0.019 Uani 1 4
O(3) O 0.75498(3) -0.15479(2) 1.40548(2) 0.019 Uani 1 4
N(125) N 0.53363(2) -0.072953(16) 1.147115(17) 0.013 Uani 1 4
C(121) C 0.35357(2) -0.196136(17) 0.997517(18) 0.013 Uani 1 4
C(122) C 0.21632(2) -0.131657(19) 1.025508(19) 0.015 Uani 1 4
C(123) C 0.24128(3) -0.03913(2) 1.11427(2) 0.016 Uani 1 4
C(124) C 0.40448(3) -0.009872(18) 1.175834(18) 0.015 Uani 1 4
C(126) C 0.51270(2) -0.163126(16) 1.060933(17) 0.013 Uani 1 4
C(21) C 0.33068(3) -0.29639(2) 0.90212(2) 0.019 Uani 1 4
C(24) C 0.44321(3) 0.08824(2) 1.27247(3) 0.021 Uani 1 4
C(111) C 1.03192(2) 0.096599(17) 1.418153(17) 0.013 Uani 1 4
C(112) C 0.91177(2) 0.013744(17) 1.364200(17) 0.013 Uani 1 4
C(113) C 0.87119(2) -0.087688(17) 1.452689(17) 0.013 Uani 1 4
H(122) H 0.092127 -0.160388 0.978867 0.029 Uani 1 4
H(123) H 0.139138 0.013407 1.137634 0.032 Uani 1 4
H(125) H 0.652288 -0.048174 1.194062 0.028 Uani 1 4
H(126) H 0.625245 -0.206642 1.042722 0.03 Uani 1 4
H(21A) H 0.446668 -0.332564 0.887991 0.04 Uani 1 4
H(21B) H 0.259569 -0.361784 0.939842 0.038 Uani 1 4
H(21C) H 0.273932 -0.266303 0.807445 0.038 Uani 1 4
H(24A) H 0.574224 0.104385 1.295173 0.036 Uani 1 4
H(24B) H 0.404202 0.071598 1.363249 0.039 Uani 1 4
H(24C) H 0.391379 0.168535 1.232908 0.039 Uani 1 4



#----------------------------------------------------------------------------#
#                   MULTIPOLE PARAMETERS                                     #
#----------------------------------------------------------------------------#

loop_
_atom_rho_multipole_atom_label
_atom_rho_multipole_coeff_Pv
_atom_rho_multipole_coeff_P00
_atom_rho_multipole_coeff_P11
_atom_rho_multipole_coeff_P1-1
_atom_rho_multipole_coeff_P10
_atom_rho_multipole_coeff_P20
_atom_rho_multipole_coeff_P21
_atom_rho_multipole_coeff_P2-1
_atom_rho_multipole_coeff_P22
_atom_rho_multipole_coeff_P2-2
_atom_rho_multipole_coeff_P30
_atom_rho_multipole_coeff_P31
_atom_rho_multipole_coeff_P3-1
_atom_rho_multipole_coeff_P32
_atom_rho_multipole_coeff_P3-2
_atom_rho_multipole_coeff_P33
_atom_rho_multipole_coeff_P3-3
_atom_rho_multipole_coeff_P40
_atom_rho_multipole_coeff_P41
_atom_rho_multipole_coeff_P4-1
_atom_rho_multipole_coeff_P42
_atom_rho_multipole_coeff_P4-2
_atom_rho_multipole_coeff_P43
_atom_rho_multipole_coeff_P4-3
_atom_rho_multipole_coeff_P44
_atom_rho_multipole_coeff_P4-4
_atom_rho_multipole_kappa
_atom_rho_multipole_kappa_prime0
_atom_rho_multipole_kappa_prime1
_atom_rho_multipole_kappa_prime2
_atom_rho_multipole_kappa_prime3
_atom_rho_multipole_kappa_prime4
Cl(1) 7.401(19) 0 0.037(8) -0.002(7) -0.044(8) -0.125(9) -0.037(11) 0.029(10)
-0.013(10) -0.022(11) 0.100(6) -0.014(6) 0.010(6) -0.002(6) -0.002(6) -0.054(6)
-0.028(6) 0.023(9) 0.002(8) 0.020(8) -0.008(8) -0.015(9) -0.012(9) 0.011(9)
0.009(8) 0.004(8) 0.979628 1 1 1 1 1
O(2) 6.115(11) 0 0.025(7) 0.007(6) -0.054(6) -0.020(7) -0.004(6) 0.005(6)
-0.048(6) -0.067(7) 0.008(6) -0.008(6) -0.010(5) 0.030(6) 0.010(5) 0.007(6)
0.019(6) 0 0 0 0 0 0 0 0 0 0.991566 0.990855 0.990855 0.990855 0.990855
0.990855
O(3) 6.072(12) 0 -0.019(7) -0.015(6) -0.054(6) -0.003(7) -0.009(7) 0.019(6)
-0.101(7) -0.002(7) 0.020(6) 0.017(6) 0.010(5) 0.033(6) -0.010(6) -0.032(6)
-0.006(6) 0 0 0 0 0 0 0 0 0 0.991566 0.990855 0.990855 0.990855 0.990855
0.990855
N(125) 4.955(18) 0 0.040(7) -0.050(8) -0.009(6) -0.101(6) -0.007(6) -0.002(6)
0.021(7) 0.005(7) -0.005(7) -0.016(6) 0.020(6) -0.010(6) -0.007(6) 0.163(7)
-0.005(7) 0 0 0 0 0 0 0 0 0 0.992395 0.972526 0.972526 0.972526 0.972526
0.972526
C(121) 4.01(2) 0 0.026(9) 0.008(9) -0.008(8) -0.196(8) -0.002(7) 0.000(7)
-0.013(8) -0.005(8) 0.012(9) 0.030(8) 0.010(8) 0.005(8) -0.003(9) 0.227(9)
0.009(9) 0 0 0 0 0 0 0 0 0 0.990939 0.990849 0.990849 0.990849 0.990849
0.990849
C(122) 4.00(2) 0 0.036(9) 0.010(9) 0.020(8) -0.220(8) 0.010(8) -0.003(8)
0.017(8) -0.012(8) 0.004(9) 0.013(9) 0.022(9) 0.012(9) 0.001(9) 0.248(9)
0.006(9) 0 0 0 0 0 0 0 0 0 0.990939 0.990849 0.990849 0.990849 0.990849
0.990849
C(123) 4.13(2) 0 0.015(9) 0.041(9) -0.002(8) -0.174(8) 0.014(8) 0.000(7)
-0.022(8) -0.017(8) 0.008(9) 0.024(9) 0.012(8) -0.010(9) -0.026(9) 0.242(9)
-0.013(9) 0 0 0 0 0 0 0 0 0 0.990939 0.990849 0.990849 0.990849 0.990849
0.990849
C(124) 4.13(2) 0 0.023(9) 0.034(9) -0.020(8) -0.195(8) -0.002(7) 0.024(7)
-0.012(8) -0.006(8) -0.009(9) 0.005(8) 0.005(8) -0.012(9) 0.000(9) 0.277(9)
0.006(9) 0 0 0 0 0 0 0 0 0 0.990939 0.990849 0.990849 0.990849 0.990849
0.990849
C(126) 4.09(2) 0 0.034(9) -0.071(8) -0.017(7) -0.207(7) 0.015(7) 0.012(7)
0.033(7) 0.042(8) 0.007(8) 0.012(8) 0.021(8) -0.010(8) -0.010(8) 0.270(9)
-0.038(9) 0 0 0 0 0 0 0 0 0 0.990939 0.990849 0.990849 0.990849 0.990849
0.990849
C(21) 4.09(4) 0 0.025(9) 0.022(9) 0.012(9) -0.013(8) -0.039(8) 0.053(8)
0.007(7) -0.011(9) 0.170(11) 0.004(9) 0.009(9) -0.065(9) -0.012(9) -0.004(9)
-0.188(9) 0 0 0 0 0 0 0 0 0 0.987597 0.980376 0.980376 0.980376 0.980376
0.980376
C(24) 4.16(4) 0 0.026(9) 0.026(9) 0.036(9) -0.016(9) 0.035(8) 0.013(8) 0.015(8)
0.022(8) 0.168(10) 0.033(10) -0.010(9) -0.035(9) 0.116(9) -0.015(9) -0.148(9) 0
0 0 0 0 0 0 0 0 0.987597 0.980376 0.980376 0.980376 0.980376 0.980376
C(111) 4.16(2) 0 0.035(9) -0.064(8) 0.002(8) -0.071(8) 0.006(7) 0.009(7)
0.067(8) 0.063(8) -0.003(9) 0.024(8) -0.017(8) -0.007(8) 0.006(8) 0.237(8)
-0.018(9) 0 0 0 0 0 0 0 0 0 0.990232 0.982826 0.982826 0.982826 0.982826
0.982826
C(112) 4.138(19) 0 -0.029(8) -0.022(8) -0.007(8) -0.252(8) -0.006(7) -0.003(7)
-0.067(8) 0.023(8) -0.015(9) 0.004(8) 0.026(8) -0.003(8) 0.005(8) 0.291(9)
0.021(9) 0 0 0 0 0 0 0 0 0 0.990232 0.982826 0.982826 0.982826 0.982826
0.982826
C(113) 4.11(2) 0 0.059(8) -0.036(8) -0.010(8) -0.251(8) 0.016(7) -0.004(7)
0.072(8) 0.019(7) 0.001(9) -0.009(8) -0.005(8) -0.016(8) 0.012(8) 0.293(9)
-0.024(9) 0 0 0 0 0 0 0 0 0 0.990232 0.982826 0.982826 0.982826 0.982826
0.982826
H(122) 0.833(8) 0 -0.025(6) -0.018(5) 0.142(6) 0.062(8) 0 0 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 1.187747 1.187747 1.187747 1.187747 1.187747 1.187747
H(123) 0.833(8) 0 -0.025(6) -0.018(5) 0.142(6) 0.062(8) 0 0 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 1.187747 1.187747 1.187747 1.187747 1.187747 1.187747
H(125) 0.734(13) 0 -0.022(8) -0.046(9) 0.133(10) 0.178(15) 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0 0 1.187747 1.187747 1.187747 1.187747 1.187747 1.187747
H(126) 0.833(8) 0 -0.025(6) -0.018(5) 0.142(6) 0.062(8) 0 0 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 1.187747 1.187747 1.187747 1.187747 1.187747 1.187747
H(21A) 0.889(10) 0 0.015(6) 0.000(6) 0.115(7) 0.052(9) 0 0 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 1.173875 1.173875 1.173875 1.173875 1.173875 1.173875
H(21B) 0.889(10) 0 0.015(6) 0.000(6) 0.115(7) 0.052(9) 0 0 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 1.173875 1.173875 1.173875 1.173875 1.173875 1.173875
H(21C) 0.889(10) 0 0.015(6) 0.000(6) 0.115(7) 0.052(9) 0 0 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 1.173875 1.173875 1.173875 1.173875 1.173875 1.173875
H(24A) 0.845(10) 0 0.010(6) -0.077(6) 0.124(7) 0.021(9) 0 0 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 1.173875 1.173875 1.173875 1.173875 1.173875 1.173875
H(24B) 0.845(10) 0 0.010(6) -0.077(6) 0.124(7) 0.021(9) 0 0 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 1.173875 1.173875 1.173875 1.173875 1.173875 1.173875
H(24C) 0.845(10) 0 0.010(6) -0.077(6) 0.124(7) 0.021(9) 0 0 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 1.173875 1.173875 1.173875 1.173875 1.173875 1.173875

loop_
_atom_local_axes_atom_label
_atom_local_axes_atom0
_atom_local_axes_ax1
_atom_local_axes_atom1
_atom_local_axes_atom2
_atom_local_axes_ax2
CL(1) C(111) Z CL(1) C(112) Y
O(2) C(112) Z O(2) H(125) Y
O(3) C(113) Z O(3) C(112) Y
N(125) C(126) X N(125) C(124) Y
C(121) C(126) X C(121) C(122) Y
C(122) C(121) X C(122) C(123) Y
C(123) C(124) X C(123) C(122) Y
C(124) N(125) X C(124) C(123) Y
C(126) C(121) X C(126) N(125) Y
C(21) H(21C) Z C(21) H(21B) Y
C(24) H(24B) Z C(24) H(24A) Y
C(111) C(112) X C(111) CL(1) Y
C(112) C(113) X C(112) C(111) Y
C(113) O(3) X C(113) C(112) Y
H(122) C(122) Z H(122) C(121) Y
H(123) C(123) Z H(123) C(124) Y
H(125) N(125) Z H(125) O(2) Y
H(126) C(126) Z H(126) N(125) Y
H(21A) C(21) Z H(21A) H(21C) Y
H(21B) C(21) Z H(21B) H(21C) Y
H(21C) C(21) Z H(21C) H(21A) Y
H(24A) C(24) Z H(24A) H(24C) Y
H(24B) C(24) Z H(24B) H(24A) Y
H(24C) C(24) Z H(24C) H(24A) Y


#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
CL(1) C(111) 1.74201(19) 1_555 1_555 yes
O(2) C(112) 1.2605(3) 1_555 1_555 yes
O(3) C(113) 1.2418(3) 1_555 1_555 yes
N(125) C(124) 1.3455(3) 1_555 1_555 yes
N(125) C(126) 1.3515(3) 1_555 1_555 yes
N(125) H(125) 1.03300(18) 1_555 1_555 yes
C(121) C(122) 1.4050(3) 1_555 1_555 yes
C(121) C(126) 1.3861(2) 1_555 1_555 yes
C(121) C(21) 1.4999(3) 1_555 1_555 yes
C(122) C(123) 1.3894(3) 1_555 1_555 yes
C(122) H(122) 1.08299(19) 1_555 1_555 yes
C(123) C(124) 1.3975(3) 1_555 1_555 yes
C(123) H(123) 1.0830(2) 1_555 1_555 yes
C(124) C(24) 1.4953(3) 1_555 1_555 yes
C(126) H(126) 1.08300(18) 1_555 1_555 yes
C(21) H(21A) 1.0590(2) 1_555 1_555 yes
C(21) H(21B) 1.0590(3) 1_555 1_555 yes
C(21) H(21C) 1.0590(2) 1_555 1_555 yes
C(24) H(24A) 1.0590(3) 1_555 1_555 yes
C(24) H(24B) 1.0590(3) 1_555 1_555 yes
C(24) H(24C) 1.0590(3) 1_555 1_555 yes
C(111) C(112) 1.3977(3) 1_555 1_555 yes
C(111) C(113) 1.4226(2) 1_555 3_758 yes

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C(124) N(125) C(126) 122.931(17) 1_555 1_555 1_555 yes
C(124) N(125) H(125) 116.234(18) 1_555 1_555 1_555 yes
C(126) N(125) H(125) 120.831(18) 1_555 1_555 1_555 yes
C(122) C(121) C(126) 117.427(17) 1_555 1_555 1_555 yes
C(122) C(121) C(21) 121.820(17) 1_555 1_555 1_555 yes
C(126) C(121) C(21) 120.751(18) 1_555 1_555 1_555 yes
C(121) C(122) C(123) 120.577(18) 1_555 1_555 1_555 yes
C(121) C(122) H(122) 116.949(19) 1_555 1_555 1_555 yes
C(123) C(122) H(122) 122.401(19) 1_555 1_555 1_555 yes
C(122) C(123) C(124) 119.612(18) 1_555 1_555 1_555 yes
C(122) C(123) H(123) 122.884(19) 1_555 1_555 1_555 yes
C(124) C(123) H(123) 117.50(2) 1_555 1_555 1_555 yes
N(125) C(124) C(123) 118.588(18) 1_555 1_555 1_555 yes
N(125) C(124) C(24) 118.121(19) 1_555 1_555 1_555 yes
C(123) C(124) C(24) 123.292(19) 1_555 1_555 1_555 yes
N(125) C(126) C(121) 120.864(17) 1_555 1_555 1_555 yes
N(125) C(126) H(126) 117.077(16) 1_555 1_555 1_555 yes
C(121) C(126) H(126) 122.049(17) 1_555 1_555 1_555 yes
C(121) C(21) H(21A) 112.421(18) 1_555 1_555 1_555 yes
C(121) C(21) H(21B) 107.904(19) 1_555 1_555 1_555 yes
C(121) C(21) H(21C) 109.86(2) 1_555 1_555 1_555 yes
H(21A) C(21) H(21B) 109.22(2) 1_555 1_555 1_555 yes
H(21A) C(21) H(21C) 104.23(2) 1_555 1_555 1_555 yes
H(21B) C(21) H(21C) 113.27(2) 1_555 1_555 1_555 yes
C(124) C(24) H(24A) 110.99(2) 1_555 1_555 1_555 yes
C(124) C(24) H(24B) 113.34(2) 1_555 1_555 1_555 yes
C(124) C(24) H(24C) 111.79(2) 1_555 1_555 1_555 yes
H(24A) C(24) H(24B) 106.38(2) 1_555 1_555 1_555 yes
H(24A) C(24) H(24C) 104.16(2) 1_555 1_555 1_555 yes
H(24B) C(24) H(24C) 109.65(2) 1_555 1_555 1_555 yes
CL(1) C(111) C(112) 118.348(13) 1_555 1_555 1_555 yes
CL(1) C(111) C(113) 118.235(14) 1_555 1_555 3_758 yes
C(112) C(111) C(113) 123.373(17) 1_555 1_555 3_758 yes
O(2) C(112) C(111) 124.246(19) 1_555 1_555 1_555 yes
O(3) C(113) C(111) 124.947(19) 1_555 1_555 3_758 yes

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
C(124) N(125) C(126) C(121) -0.532(18) 1_555 1_555 1_555 1_555 yes
C(126) N(125) C(124) C(123) 0.276(19) 1_555 1_555 1_555 1_555 yes
C(126) N(125) C(124) C(24) -179.78(3) 1_555 1_555 1_555 1_555 yes
C(124) N(125) C(126) H(126) 178.32(3) 1_555 1_555 1_555 1_555 yes
H(125) N(125) C(124) C(123) 179.53(3) 1_555 1_555 1_555 1_555 yes
H(125) N(125) C(124) C(24) -0.530(18) 1_555 1_555 1_555 1_555 yes
H(125) N(125) C(126) C(121) -179.75(3) 1_555 1_555 1_555 1_555 yes
H(125) N(125) C(126) H(126) -0.897(16) 1_555 1_555 1_555 1_555 yes
C(122) C(121) C(126) N(125) 0.589(18) 1_555 1_555 1_555 1_555 yes
C(126) C(121) C(122) C(123) -0.430(19) 1_555 1_555 1_555 1_555 yes
C(126) C(121) C(122) H(122) -177.38(3) 1_555 1_555 1_555 1_555 yes
C(122) C(121) C(126) H(126) -178.20(3) 1_555 1_555 1_555 1_555 yes
C(21) C(121) C(122) C(123) -179.95(3) 1_555 1_555 1_555 1_555 yes
C(21) C(121) C(122) H(122) 3.092(18) 1_555 1_555 1_555 1_555 yes
C(122) C(121) C(21) H(21A) 176.74(3) 1_555 1_555 1_555 1_555 yes
C(122) C(121) C(21) H(21B) -62.77(2) 1_555 1_555 1_555 1_555 yes
C(122) C(121) C(21) H(21C) 61.16(2) 1_555 1_555 1_555 1_555 yes
C(21) C(121) C(126) N(125) -179.88(3) 1_555 1_555 1_555 1_555 yes
C(21) C(121) C(126) H(126) 1.326(18) 1_555 1_555 1_555 1_555 yes
C(126) C(121) C(21) H(21A) -2.774(18) 1_555 1_555 1_555 1_555 yes
C(126) C(121) C(21) H(21B) 117.72(3) 1_555 1_555 1_555 1_555 yes
C(126) C(121) C(21) H(21C) -118.35(3) 1_555 1_555 1_555 1_555 yes
C(121) C(122) C(123) C(124) 0.198(19) 1_555 1_555 1_555 1_555 yes
C(121) C(122) C(123) H(123) 179.21(3) 1_555 1_555 1_555 1_555 yes
H(122) C(122) C(123) C(124) 176.98(3) 1_555 1_555 1_555 1_555 yes
H(122) C(122) C(123) H(123) -4.007(19) 1_555 1_555 1_555 1_555 yes
C(122) C(123) C(124) N(125) -0.109(19) 1_555 1_555 1_555 1_555 yes
C(122) C(123) C(124) C(24) 179.95(3) 1_555 1_555 1_555 1_555 yes
H(123) C(123) C(124) N(125) -179.17(3) 1_555 1_555 1_555 1_555 yes
H(123) C(123) C(124) C(24) 0.89(2) 1_555 1_555 1_555 1_555 yes
N(125) C(124) C(24) H(24A) 9.41(2) 1_555 1_555 1_555 1_555 yes
N(125) C(124) C(24) H(24B) -110.23(3) 1_555 1_555 1_555 1_555 yes
N(125) C(124) C(24) H(24C) 125.24(3) 1_555 1_555 1_555 1_555 yes
C(123) C(124) C(24) H(24A) -170.65(3) 1_555 1_555 1_555 1_555 yes
C(123) C(124) C(24) H(24B) 69.71(3) 1_555 1_555 1_555 1_555 yes
C(123) C(124) C(24) H(24C) -54.82(2) 1_555 1_555 1_555 1_555 yes
CL(1) C(111) C(112) O(2) 2.196(18) 1_555 1_555 1_555 1_555 yes
C(113) C(111) C(112) O(2) -175.34(3) 3_758 1_555 1_555 1_555 yes
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_(2,6)_shelx
_database_code_depnum_ccdc_archive 'CCDC 1478085'
_audit_update_record             
;
2016-05-04 deposited with the CCDC.
2016-06-13 downloaded from the CCDC.
;

_chemical_formula_moiety         
;
C6 H Cl2 O4, C7 H10 N  
;
_chemical_formula_sum            'C13 H11 Cl2 N O4'
_chemical_formula_weight         316.13
_chemical_compound_source        commercial

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_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_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.0071(3)
_cell_length_b                   9.0326(3)
_cell_length_c                   9.0768(3)
_cell_angle_alpha                93.526(2)
_cell_angle_beta                 104.359(2)
_cell_angle_gamma                110.821(2)
_cell_volume                     659.48(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    14000
_cell_measurement_theta_min      2.348
_cell_measurement_theta_max      50.522
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_diffrn    1.592
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             324
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.504
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5290
_exptl_absorpt_correction_T_max  0.7496
_exptl_absorpt_process_details   'SADABS, Bruker(2001)'
#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      0.215013E-1
_diffrn_orient_matrix_UB_21      -0.595806E-1
_diffrn_orient_matrix_UB_31      -0.1067006
_diffrn_orient_matrix_UB_12      -0.1012639
_diffrn_orient_matrix_UB_22      -0.314661E-1
_diffrn_orient_matrix_UB_32      -0.563804E-1
_diffrn_orient_matrix_UB_13      -0.8928E-3
_diffrn_orient_matrix_UB_23      0.796033E-1
_diffrn_orient_matrix_UB_33      -0.834197E-1
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_number            62289
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.35
_diffrn_reflns_theta_max         50.52
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_reflns_Friedel_coverage         0
_reflns_number_total             14000
_reflns_number_gt                11619
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
 Scaled and merged with Sortav
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0485P)²+0.0127P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_number_reflns         14000
_refine_ls_number_parameters     225
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0346
_refine_ls_R_factor_gt           0.0264
_refine_ls_wR_factor_ref         0.083
_refine_ls_wR_factor_gt          0.0799
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.715
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.067

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.05986(2) 0.84855(2) 0.41648(2) 0.01460(2) Uani 1 1 d . . . . .
Cl2 Cl 0.29223(2) 0.26225(2) 0.41977(2) 0.01941(2) Uani 1 1 d . . . . .
O3 O 0.33012(4) 0.49422(4) 0.68736(3) 0.01696(4) Uani 1 1 d . . . . .
O2 O 0.20907(3) 0.72767(3) 0.69119(3) 0.01352(4) Uani 1 1 d . . . . .
O5 O 0.11160(4) 0.36093(3) 0.14775(3) 0.01553(4) Uani 1 1 d . . . . .
O6 O 0.02741(4) 0.61449(4) 0.14765(3) 0.01627(4) Uani 1 1 d . . . . .
N125 N 0.50654(3) 0.82731(3) 0.89758(3) 0.01165(3) Uani 1 1 d . . . . .
C121 C 0.77600(4) 1.02764(5) 0.95669(5) 0.01609(5) Uani 1 1 d . . . . .
C122 C 0.81921(5) 0.97038(5) 1.09361(5) 0.01817(6) Uani 1 1 d . . . . .
C123 C 0.70314(4) 0.83878(5) 1.12955(4) 0.01628(5) Uani 1 1 d . . . . .
C124 C 0.54339(4) 0.76748(4) 1.02881(4) 0.01242(4) Uani 1 1 d . . . . .
C126 C 0.61606(4) 0.95317(4) 0.85736(4) 0.01265(4) Uani 1 1 d . . . . .
C24 C 0.40597(5) 0.63059(5) 1.05747(4) 0.01580(5) Uani 1 1 d . . . . .
C26 C 0.55608(5) 1.00412(5) 0.70725(4) 0.01608(5) Uani 1 1 d . . . . .
C111 C 0.11494(4) 0.68332(4) 0.41978(3) 0.01117(4) Uani 1 1 d . . . . .
C112 C 0.18848(4) 0.65125(4) 0.56268(3) 0.01061(4) Uani 1 1 d . . . . .
C113 C 0.25396(4) 0.51444(4) 0.56365(3) 0.01159(4) Uani 1 1 d . . . . .
C114 C 0.22372(4) 0.41757(4) 0.41704(4) 0.01262(4) Uani 1 1 d . . . . .
C115 C 0.14267(4) 0.44834(4) 0.28271(4) 0.01198(4) Uani 1 1 d . . . . .
C116 C 0.08893(4) 0.58934(4) 0.27809(3) 0.01145(4) Uani 1 1 d . . . . .
H121 H 0.8511(11) 1.1191(11) 0.9292(11) 0.023(2) Uiso 1 1 d . . . . .
H122 H 0.9286(12) 1.0212(12) 1.1609(11) 0.027(2) Uiso 1 1 d . . . . .
H123 H 0.7266(12) 0.7931(12) 1.2246(12) 0.032(2) Uiso 1 1 d . . . . .
H125 H 0.4036(11) 0.7824(11) 0.8319(10) 0.022(2) Uiso 1 1 d . . . . .
H24A H 0.3580(13) 0.5420(13) 0.9744(13) 0.034(2) Uiso 1 1 d . . . . .
H24B H 0.3206(14) 0.6670(14) 1.0742(13) 0.040(3) Uiso 1 1 d . . . . .
H24C H 0.4513(16) 0.5932(15) 1.1597(15) 0.053(3) Uiso 1 1 d . . . . .
H26A H 0.5278(13) 0.9197(13) 0.6223(12) 0.037(3) Uiso 1 1 d . . . . .
H26B H 0.4585(13) 1.0230(13) 0.7030(12) 0.035(2) Uiso 1 1 d . . . . .
H26C H 0.6294(15) 1.0997(15) 0.7007(14) 0.048(3) Uiso 1 1 d . . . . .
H5 H 0.0619(14) 0.4005(14) 0.0710(14) 0.047(3) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   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 C111 1.7317(3) . ?
Cl2 C114 1.7210(3) . ?
O3 C113 1.2236(4) . ?
O2 C112 1.2547(4) . ?
O5 C115 1.3252(4) . ?
O5 H5 0.896(12) . ?
O6 C116 1.2481(4) . ?
N125 C126 1.3532(4) . ?
N125 C124 1.3534(4) . ?
N125 H125 0.899(9) . ?
C121 C126 1.3903(5) . ?
C121 C122 1.3949(6) . ?
C121 H121 0.956(9) . ?
C122 C123 1.3949(6) . ?
C122 H122 0.949(10) . ?
C123 C124 1.3919(5) . ?
C123 H123 0.987(10) . ?
C124 C24 1.4966(5) . ?
C126 C26 1.4996(5) . ?
C24 H24A 0.956(11) . ?
C24 H24B 0.977(11) . ?
C24 H24C 1.044(13) . ?
C26 H26A 0.966(11) . ?
C26 H26B 0.945(11) . ?
C26 H26C 0.897(12) . ?
C111 C112 1.4006(4) . ?
C111 C116 1.4157(4) . ?
C112 C113 1.5466(4) . ?
C113 C114 1.4554(4) . ?
C114 C115 1.3569(5) . ?
C115 C116 1.5143(5) . ?

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
C115 O5 H5 110.5(8) . . ?
C126 N125 C124 123.96(3) . . ?
C126 N125 H125 116.7(6) . . ?
C124 N125 H125 119.3(6) . . ?
C126 C121 C122 119.38(3) . . ?
C126 C121 H121 117.9(5) . . ?
C122 C121 H121 122.7(6) . . ?
C121 C122 C123 120.16(3) . . ?
C121 C122 H122 119.2(6) . . ?
C123 C122 H122 120.7(6) . . ?
C124 C123 C122 119.28(3) . . ?
C124 C123 H123 117.0(6) . . ?
C122 C123 H123 123.7(6) . . ?
N125 C124 C123 118.61(3) . . ?
N125 C124 C24 116.98(3) . . ?
C123 C124 C24 124.39(3) . . ?
N125 C126 C121 118.60(3) . . ?
N125 C126 C26 117.42(3) . . ?
C121 C126 C26 123.98(3) . . ?
C124 C24 H24A 112.1(6) . . ?
C124 C24 H24B 109.7(7) . . ?
H24A C24 H24B 109.9(9) . . ?
C124 C24 H24C 109.4(7) . . ?
H24A C24 H24C 109.6(9) . . ?
H24B C24 H24C 105.9(10) . . ?
C126 C26 H26A 110.3(6) . . ?
C126 C26 H26B 110.5(7) . . ?
H26A C26 H26B 106.8(9) . . ?
C126 C26 H26C 110.3(8) . . ?
H26A C26 H26C 114.7(10) . . ?
H26B C26 H26C 104.0(10) . . ?
C112 C111 C116 122.67(3) . . ?
C112 C111 Cl1 118.50(2) . . ?
C116 C111 Cl1 118.80(2) . . ?
O2 C112 C111 124.96(3) . . ?
O2 C112 C113 116.95(3) . . ?
C111 C112 C113 118.07(3) . . ?
O3 C113 C114 123.31(3) . . ?
O3 C113 C112 118.38(3) . . ?
C114 C113 C112 118.30(3) . . ?
C115 C114 C113 120.82(3) . . ?
C115 C114 Cl2 121.21(3) . . ?
C113 C114 Cl2 117.96(2) . . ?
O5 C115 C114 122.14(3) . . ?
O5 C115 C116 116.13(3) . . ?
C114 C115 C116 121.68(3) . . ?
O6 C116 C111 125.34(3) . . ?
O6 C116 C115 116.47(3) . . ?
C111 C116 C115 118.17(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
C126 C121 C122 C123 0.53(6) . . . . ?
C121 C122 C123 C124 -1.18(7) . . . . ?
C126 N125 C124 C123 0.07(5) . . . . ?
C126 N125 C124 C24 178.33(3) . . . . ?
C122 C123 C124 N125 0.88(6) . . . . ?
C122 C123 C124 C24 -177.24(4) . . . . ?
C124 N125 C126 C121 -0.72(5) . . . . ?
C124 N125 C126 C26 179.52(3) . . . . ?
C122 C121 C126 N125 0.40(6) . . . . ?
C122 C121 C126 C26 -179.86(4) . . . . ?
C116 C111 C112 O2 -177.51(3) . . . . ?
Cl1 C111 C112 O2 4.62(4) . . . . ?
C116 C111 C112 C113 4.19(4) . . . . ?
Cl1 C111 C112 C113 -173.68(2) . . . . ?
O2 C112 C113 O3 -4.21(5) . . . . ?
C111 C112 C113 O3 174.23(3) . . . . ?
O2 C112 C113 C114 176.58(3) . . . . ?
C111 C112 C113 C114 -4.98(4) . . . . ?
O3 C113 C114 C115 -178.04(3) . . . . ?
C112 C113 C114 C115 1.12(5) . . . . ?
O3 C113 C114 Cl2 2.52(5) . . . . ?
C112 C113 C114 Cl2 -178.31(2) . . . . ?
C113 C114 C115 O5 -179.15(3) . . . . ?
Cl2 C114 C115 O5 0.27(5) . . . . ?
C113 C114 C115 C116 3.49(5) . . . . ?
Cl2 C114 C115 C116 -177.09(2) . . . . ?
C112 C111 C116 O6 -178.38(3) . . . . ?
Cl1 C111 C116 O6 -0.51(5) . . . . ?
C112 C111 C116 C115 0.26(5) . . . . ?
Cl1 C111 C116 C115 178.12(2) . . . . ?
O5 C115 C116 O6 -3.14(4) . . . . ?
C114 C115 C116 O6 174.37(3) . . . . ?
O5 C115 C116 C111 178.10(3) . . . . ?
C114 C115 C116 C111 -4.38(5) . . . . ?

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

data_1_(2,6)_xd
_database_code_depnum_ccdc_archive 'CCDC 1478086'
_audit_update_record             
;
2016-05-04 deposited with the CCDC.
2016-06-13 downloaded from the CCDC.
;

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         
;
C6 H Cl2 O4, C7 H10 N  
;
_chemical_formula_sum            'C13 H11 Cl2 N O4'
_chemical_formula_weight         316.13
_chemical_compound_source        commercial

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_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                   9.0071(3)
_cell_length_b                   9.0326(3)
_cell_length_c                   9.0768(3)
_cell_angle_alpha                93.526(2)
_cell_angle_beta                 104.359(2)
_cell_angle_gamma                110.821(2)
_cell_volume                     659.48(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    14002
_cell_measurement_theta_min      1
_cell_measurement_theta_max      50.52
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_diffrn    1.592
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             324
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.504
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5290
_exptl_absorpt_correction_T_max  0.7496
_exptl_absorpt_process_details   'SADABS, Bruker(2001)'
#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      0.215013E-1
_diffrn_orient_matrix_UB_21      -0.595806E-1
_diffrn_orient_matrix_UB_31      -0.1067006
_diffrn_orient_matrix_UB_12      -0.1012639
_diffrn_orient_matrix_UB_22      -0.314661E-1
_diffrn_orient_matrix_UB_32      -0.563804E-1
_diffrn_orient_matrix_UB_13      -0.8928E-3
_diffrn_orient_matrix_UB_23      0.796033E-1
_diffrn_orient_matrix_UB_33      -0.834197E-1
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_number            62289
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.35
_diffrn_reflns_theta_max         50.52
_diffrn_reflns_theta_full        50.52
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_reflns_number_total             14002
_reflns_number_gt                11621
_reflns_threshold_expression     >2σ(I)
_diffrn_reflns_reduction_process 
;
 Scaled and merged with Sortav
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
        ?
;
_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
        calc w1 = 1/[s²(Fo)]
;
_refine_ls_extinction_method     'Becker-Coppens type 1 Lorentzian isotropic'
_refine_ls_extinction_expression 
;
        Becker, P.J. & Coppens, P. (1974) Acta Cryst., A30, 129-153.
;
_refine_ls_extinction_coef       0.024(7)
_refine_ls_number_reflns         11968
_refine_ls_number_parameters     543
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.029
_refine_ls_R_factor_gt           0.018
_refine_ls_wR_factor_ref         0.02
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_shift/su_max          0
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.041

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, 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_symmetry_multiplicity
Cl(1) Cl 0.059860(8) 0.848554(7) 0.416495(7) 0.014 Uani 1 2
Cl(2) Cl 0.292218(10) 0.262255(8) 0.419767(8) 0.019 Uani 1 2
O(3) O 0.33002(4) 0.49423(4) 0.68737(3) 0.017 Uani 1 2
O(2) O 0.20902(3) 0.72761(3) 0.69116(3) 0.013 Uani 1 2
O(5) O 0.11144(4) 0.36110(3) 0.14771(3) 0.015 Uani 1 2
O(6) O 0.02747(4) 0.61452(3) 0.14778(3) 0.016 Uani 1 2
N(125) N 0.50653(3) 0.82725(3) 0.89761(3) 0.011 Uani 1 2
C(121) C 0.77605(3) 1.02777(3) 0.95661(4) 0.016 Uani 1 2
C(122) C 0.81936(3) 0.97050(4) 1.09371(4) 0.018 Uani 1 2
C(123) C 0.70309(3) 0.83871(4) 1.12959(3) 0.016 Uani 1 2
C(124) C 0.54328(3) 0.76740(3) 1.02871(3) 0.012 Uani 1 2
C(126) C 0.61596(3) 0.95312(3) 0.85733(3) 0.012 Uani 1 2
C(24) C 0.40605(3) 0.63070(3) 1.05751(3) 0.016 Uani 1 2
C(26) C 0.55610(4) 1.00414(4) 0.70725(3) 0.016 Uani 1 2
C(111) C 0.11498(3) 0.68335(3) 0.41979(3) 0.011 Uani 1 2
C(112) C 0.18856(3) 0.65128(3) 0.56269(2) 0.01 Uani 1 2
C(113) C 0.25394(3) 0.51443(3) 0.56358(3) 0.011 Uani 1 2
C(114) C 0.22375(3) 0.41755(3) 0.41711(3) 0.012 Uani 1 2
C(115) C 0.14263(3) 0.44831(3) 0.28261(3) 0.012 Uani 1 2
C(116) C 0.08894(3) 0.58932(3) 0.27810(3) 0.011 Uani 1 2
H(121) H 0.861867 1.131895 0.925721 0.033 Uani 1 2
H(122) H 0.945003 1.028303 1.171827 0.035 Uani 1 2
H(123) H 0.729624 0.78848 1.234435 0.033 Uani 1 2
H(125) H 0.384012 0.773918 0.819443 0.026 Uani 1 2
H(24A) H 0.351172 0.529621 0.963385 0.035 Uani 1 2
H(24B) H 0.310876 0.670768 1.076481 0.035 Uani 1 2
H(24C) H 0.451359 0.590538 1.163237 0.037 Uani 1 2
H(26A) H 0.523615 0.909509 0.611102 0.034 Uani 1 2
H(26B) H 0.444069 1.026528 0.701342 0.034 Uani 1 2
H(26C) H 0.645925 1.11877 0.699563 0.037 Uani 1 2
H(5) H 0.055674 0.404258 0.063311 0.028 Uani 1 2



#----------------------------------------------------------------------------#
#                   MULTIPOLE PARAMETERS                                     #
#----------------------------------------------------------------------------#

loop_
_atom_rho_multipole_atom_label
_atom_rho_multipole_coeff_Pv
_atom_rho_multipole_coeff_P00
_atom_rho_multipole_coeff_P11
_atom_rho_multipole_coeff_P1-1
_atom_rho_multipole_coeff_P10
_atom_rho_multipole_coeff_P20
_atom_rho_multipole_coeff_P21
_atom_rho_multipole_coeff_P2-1
_atom_rho_multipole_coeff_P22
_atom_rho_multipole_coeff_P2-2
_atom_rho_multipole_coeff_P30
_atom_rho_multipole_coeff_P31
_atom_rho_multipole_coeff_P3-1
_atom_rho_multipole_coeff_P32
_atom_rho_multipole_coeff_P3-2
_atom_rho_multipole_coeff_P33
_atom_rho_multipole_coeff_P3-3
_atom_rho_multipole_coeff_P40
_atom_rho_multipole_coeff_P41
_atom_rho_multipole_coeff_P4-1
_atom_rho_multipole_coeff_P42
_atom_rho_multipole_coeff_P4-2
_atom_rho_multipole_coeff_P43
_atom_rho_multipole_coeff_P4-3
_atom_rho_multipole_coeff_P44
_atom_rho_multipole_coeff_P4-4
_atom_rho_multipole_kappa
_atom_rho_multipole_kappa_prime0
_atom_rho_multipole_kappa_prime1
_atom_rho_multipole_kappa_prime2
_atom_rho_multipole_kappa_prime3
_atom_rho_multipole_kappa_prime4
Cl(1) 7.20(2) 0 0.005(9) -0.017(9) -0.017(9) -0.175(13) 0.066(12) -0.069(13)
-0.039(12) 0.011(12) 0.092(8) -0.013(8) -0.015(8) -0.005(7) 0.004(7) 0.006(7)
0.004(7) 0.051(12) 0.015(10) -0.006(10) 0.031(11) 0.008(11) -0.013(11)
-0.012(10) -0.021(10) -0.009(10) 1.005075 1 1 1 1 1
Cl(2) 7.20(2) 0 0.048(10) -0.014(9) -0.008(10) -0.143(13) -0.052(12) -0.063(12)
-0.042(13) 0.003(12) 0.081(8) -0.002(8) 0.018(8) 0.035(8) 0.020(8) -0.048(8)
0.030(8) 0.043(12) -0.005(11) 0.006(11) 0.033(11) 0.004(12) 0.012(11)
-0.018(11) -0.005(11) 0.021(11) 1.005075 1 1 1 1 1
O(3) 6.095(14) 0 0.022(8) 0.016(8) -0.064(8) 0.007(9) -0.009(8) 0.003(8)
-0.126(8) 0.012(8) 0.014(8) -0.001(8) -0.018(8) 0.015(7) -0.009(7) 0.016(7)
-0.007(7) 0 0 0 0 0 0 0 0 0 0.99506 0.963494 0.963494 0.963494 0.963494
0.963494
O(2) 6.129(13) 0 0.018(7) 0.014(7) -0.054(8) -0.011(8) -0.001(7) 0.006(7)
-0.030(7) -0.092(7) 0.024(7) -0.007(7) 0.000(7) 0.017(7) 0.013(7) -0.006(6)
0.012(6) 0 0 0 0 0 0 0 0 0 0.99506 0.963494 0.963494 0.963494 0.963494 0.963494
O(5) 6.062(17) 0 -0.009(7) -0.071(7) -0.062(9) -0.020(9) 0.016(8) 0.012(8)
0.019(8) 0.009(7) 0.069(8) -0.017(7) -0.012(7) 0.033(7) 0.007(7) -0.002(7)
-0.013(6) 0 0 0 0 0 0 0 0 0 0.996698 1.005727 1.005727 1.005727 1.005727
1.005727
O(6) 6.087(14) 0 -0.002(8) 0.022(8) -0.065(8) -0.011(9) -0.017(8) -0.004(8)
-0.105(8) -0.034(8) 0.020(8) -0.005(7) 0.000(7) 0.008(7) 0.010(7) -0.004(7)
0.009(7) 0 0 0 0 0 0 0 0 0 0.99506 0.963494 0.963494 0.963494 0.963494 0.963494
N(125) 5.03(2) 0 -0.001(8) -0.022(9) -0.017(7) -0.094(8) 0.014(8) -0.015(7)
-0.003(8) 0.023(8) 0.007(8) 0.002(8) 0.018(8) -0.002(8) -0.002(8) 0.200(8)
0.015(9) 0 0 0 0 0 0 0 0 0 0.997805 0.960413 0.960413 0.960413 0.960413
0.960413
C(121) 4.06(3) 0 0.025(12) 0.003(11) -0.015(10) -0.157(10) -0.018(10) -0.017(9)
0.003(10) -0.007(10) -0.020(12) 0.011(11) 0.045(10) -0.009(11) -0.001(11)
0.239(11) -0.020(12) 0 0 0 0 0 0 0 0 0 1.001522 0.983311 0.983311 0.983311
0.983311 0.983311
C(122) 4.03(3) 0 -0.001(11) 0.043(11) -0.007(11) -0.220(11) -0.001(10)
0.001(10) 0.001(11) 0.002(11) 0.011(12) 0.029(12) -0.005(11) 0.001(11)
0.005(11) 0.243(11) -0.010(12) 0 0 0 0 0 0 0 0 0 1.001522 0.983311 0.983311
0.983311 0.983311 0.983311
C(123) 4.11(3) 0 0.013(11) 0.007(11) -0.017(10) -0.181(10) -0.025(10) -0.008(9)
-0.004(10) 0.004(10) -0.010(11) 0.009(11) 0.017(10) 0.006(11) 0.008(11)
0.256(11) 0.008(11) 0 0 0 0 0 0 0 0 0 1.001522 0.983311 0.983311 0.983311
0.983311 0.983311
C(124) 4.01(2) 0 -0.060(10) 0.029(10) -0.014(9) -0.193(9) 0.017(9) 0.005(9)
-0.045(10) -0.021(9) 0.004(11) -0.012(10) 0.023(10) 0.010(10) 0.004(10)
0.283(11) 0.012(11) 0 0 0 0 0 0 0 0 0 1.001522 0.983311 0.983311 0.983311
0.983311 0.983311
C(126) 4.04(2) 0 -0.050(10) 0.037(10) 0.004(9) -0.205(10) 0.017(9) 0.003(9)
-0.059(10) -0.037(10) -0.003(11) -0.003(10) 0.008(10) -0.002(10) -0.012(10)
0.285(11) -0.001(12) 0 0 0 0 0 0 0 0 0 1.001522 0.983311 0.983311 0.983311
0.983311 0.983311
C(24) 4.22(4) 0 0.056(11) 0.029(10) 0.042(10) 0.005(10) -0.016(10) 0.001(10)
-0.020(9) -0.061(10) 0.179(13) -0.017(12) 0.002(10) -0.017(10) -0.045(11)
0.054(10) -0.207(11) 0 0 0 0 0 0 0 0 0 0.993316 0.946598 0.946598 0.946598
0.946598 0.946598
C(26) 4.27(4) 0 0.087(12) 0.039(11) 0.031(10) -0.035(10) -0.003(10) -0.041(10)
-0.015(10) -0.036(10) 0.144(12) 0.042(12) -0.019(11) -0.045(11) -0.115(11)
-0.022(11) -0.193(11) 0 0 0 0 0 0 0 0 0 0.993316 0.946598 0.946598 0.946598
0.946598 0.946598
C(111) 4.14(2) 0 0.036(10) 0.057(10) 0.004(9) -0.079(9) -0.003(9) 0.025(9)
0.038(9) -0.060(10) -0.018(10) 0.017(10) 0.037(10) -0.024(10) -0.009(10)
0.236(11) 0.038(12) 0 0 0 0 0 0 0 0 0 0.999535 0.975545 0.975545 0.975545
0.975545 0.975545
C(112) 4.07(2) 0 -0.028(10) 0.048(10) 0.008(9) -0.241(9) 0.008(9) -0.041(9)
0.072(10) -0.045(10) 0.002(11) 0.019(10) 0.006(9) 0.009(10) 0.019(10)
-0.053(12) 0.289(11) 0 0 0 0 0 0 0 0 0 0.999535 0.975545 0.975545 0.975545
0.975545 0.975545
C(113) 4.06(2) 0 -0.041(10) -0.065(10) -0.001(9) -0.276(9) -0.003(9) 0.012(9)
-0.084(10) 0.064(10) -0.001(11) -0.002(10) 0.004(10) -0.008(10) -0.002(11)
0.308(12) -0.007(12) 0 0 0 0 0 0 0 0 0 0.999535 0.975545 0.975545 0.975545
0.975545 0.975545
C(114) 4.14(2) 0 0.050(11) 0.037(10) 0.015(9) -0.098(9) 0.005(9) -0.022(9)
0.048(10) -0.054(10) 0.005(11) 0.030(10) 0.025(10) -0.003(11) 0.013(11)
0.225(11) 0.009(12) 0 0 0 0 0 0 0 0 0 0.999535 0.975545 0.975545 0.975545
0.975545 0.975545
C(115) 4.05(2) 0 -0.009(10) 0.061(11) -0.005(9) -0.197(9) -0.019(9) -0.010(9)
-0.029(10) -0.041(10) -0.002(11) -0.002(10) 0.051(10) 0.002(11) 0.006(11)
0.286(12) 0.082(12) 0 0 0 0 0 0 0 0 0 0.999535 0.975545 0.975545 0.975545
0.975545 0.975545
C(116) 4.00(2) 0 -0.054(11) -0.054(10) -0.013(9) -0.248(10) 0.002(9) 0.000(9)
-0.087(10) 0.019(10) -0.030(10) -0.025(10) 0.022(10) 0.009(11) -0.020(11)
0.303(12) 0.000(12) 0 0 0 0 0 0 0 0 0 0.999535 0.975545 0.975545 0.975545
0.975545 0.975545
H(121) 0.847(10) 0 0.010(7) -0.012(6) 0.151(8) 0.073(10) 0 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0 1.189477 1.189477 1.189477 1.189477 1.189477 1.189477
H(122) 0.847(10) 0 0.010(7) -0.012(6) 0.151(8) 0.073(10) 0 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0 1.189477 1.189477 1.189477 1.189477 1.189477 1.189477
H(123) 0.847(10) 0 0.010(7) -0.012(6) 0.151(8) 0.073(10) 0 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0 1.189477 1.189477 1.189477 1.189477 1.189477 1.189477
H(125) 0.746(14) 0 0.009(10) -0.025(10) 0.147(11) 0.160(17) 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0 0 1.189477 1.189477 1.189477 1.189477 1.189477 1.189477
H(24A) 0.862(11) 0 0.019(7) 0.011(7) 0.132(8) 0.021(11) 0 0 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 1.170307 1.170307 1.170307 1.170307 1.170307 1.170307
H(24B) 0.862(11) 0 0.019(7) 0.011(7) 0.132(8) 0.021(11) 0 0 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 1.170307 1.170307 1.170307 1.170307 1.170307 1.170307
H(24C) 0.862(11) 0 0.019(7) 0.011(7) 0.132(8) 0.021(11) 0 0 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 1.170307 1.170307 1.170307 1.170307 1.170307 1.170307
H(26A) 0.786(11) 0 -0.006(7) -0.041(7) 0.137(8) 0.014(10) 0 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0 1.170307 1.170307 1.170307 1.170307 1.170307 1.170307
H(26B) 0.786(11) 0 -0.006(7) -0.041(7) 0.137(8) 0.014(10) 0 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0 1.170307 1.170307 1.170307 1.170307 1.170307 1.170307
H(26C) 0.786(11) 0 -0.006(7) -0.041(7) 0.137(8) 0.014(10) 0 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0 1.170307 1.170307 1.170307 1.170307 1.170307 1.170307
H(5) 0.759(15) 0 0.026(10) 0.028(10) 0.213(13) 0.103(18) 0 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0 1.191563 1.191563 1.191563 1.191563 1.191563 1.191563

loop_
_atom_local_axes_atom_label
_atom_local_axes_atom0
_atom_local_axes_ax1
_atom_local_axes_atom1
_atom_local_axes_atom2
_atom_local_axes_ax2
CL(1) C(111) Z CL(1) C(112) Y
CL(2) C(114) Z CL(2) C(115) Y
O(3) C(113) Z O(3) C(114) Y
O(2) C(112) Z O(2) H(125) Y
O(5) H(5) Z O(5) C(115) Y
O(6) C(116) Z O(6) H(5) Y
N(125) C(124) X N(125) C(126) Y
C(121) C(122) X C(121) C(126) Y
C(122) C(123) X C(122) C(121) Y
C(123) C(122) X C(123) C(124) Y
C(124) N(125) X C(124) C(123) Y
C(126) N(125) X C(126) C(121) Y
C(24) H(24A) Z C(24) H(24B) Y
C(26) H(26C) Z C(26) H(26B) Y
C(111) C(112) X C(111) C(116) Y
C(112) C(116) X C(112) C(111) Y
C(113) C(112) X C(113) C(114) Y
C(114) C(115) X C(114) C(113) Y
C(115) C(116) X C(115) C(114) Y
C(116) C(115) X C(116) C(111) Y
H(121) C(121) Z H(121) C(126) Y
H(122) C(122) Z H(122) C(121) Y
H(123) C(123) Z H(123) C(124) Y
H(125) N(125) Z H(125) O(2) Y
H(24A) C(24) Z H(24A) H(24B) Y
H(24B) C(24) Z H(24B) H(24A) Y
H(24C) C(24) Z H(24C) H(24B) Y
H(26A) C(26) Z H(26A) H(26B) Y
H(26B) C(26) Z H(26B) H(26C) Y
H(26C) C(26) Z H(26C) H(26B) Y
H(5) O(5) Z H(5) C(115) Y


#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
CL(1) C(111) 1.7318(2) 1_555 1_555 yes
CL(2) C(114) 1.7205(2) 1_555 1_555 yes
O(3) C(113) 1.2238(3) 1_555 1_555 yes
O(2) C(112) 1.2543(3) 1_555 1_555 yes
O(5) C(115) 1.3237(3) 1_555 1_555 yes
O(5) H(5) 0.9880(3) 1_555 1_555 yes
O(6) C(116) 1.2472(3) 1_555 1_555 yes
N(125) C(124) 1.3523(3) 1_555 1_555 yes
N(125) C(126) 1.3532(3) 1_555 1_555 yes
N(125) H(125) 1.0700(2) 1_555 1_555 yes
C(121) C(122) 1.3965(4) 1_555 1_555 yes
C(121) C(126) 1.3913(4) 1_555 1_555 yes
C(121) H(121) 1.0880(3) 1_555 1_555 yes
C(122) C(123) 1.3966(4) 1_555 1_555 yes
C(122) H(122) 1.0920(3) 1_555 1_555 yes
C(123) C(124) 1.3928(3) 1_555 1_555 yes
C(123) H(123) 1.0890(3) 1_555 1_555 yes
C(124) C(24) 1.4953(3) 1_555 1_555 yes
C(126) C(26) 1.4995(4) 1_555 1_555 yes
C(24) H(24A) 1.0870(3) 1_555 1_555 yes
C(24) H(24B) 1.0870(3) 1_555 1_555 yes
C(24) H(24C) 1.0830(3) 1_555 1_555 yes
C(26) H(26A) 1.0870(3) 1_555 1_555 yes
C(26) H(26B) 1.0870(3) 1_555 1_555 yes
C(26) H(26C) 1.0830(3) 1_555 1_555 yes
C(111) C(112) 1.4007(3) 1_555 1_555 yes
C(111) C(116) 1.4158(3) 1_555 1_555 yes
C(113) C(114) 1.4545(3) 1_555 1_555 yes
C(114) C(115) 1.3583(3) 1_555 1_555 yes
C(115) C(116) 1.5141(3) 1_555 1_555 yes

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C(115) O(5) H(5) 110.44(3) 1_555 1_555 1_555 yes
C(124) N(125) C(126) 124.03(2) 1_555 1_555 1_555 yes
C(124) N(125) H(125) 119.34(2) 1_555 1_555 1_555 yes
C(126) N(125) H(125) 116.63(2) 1_555 1_555 1_555 yes
C(122) C(121) C(126) 119.33(2) 1_555 1_555 1_555 yes
C(122) C(121) H(121) 122.42(3) 1_555 1_555 1_555 yes
C(126) C(121) H(121) 118.22(3) 1_555 1_555 1_555 yes
C(121) C(122) C(123) 120.10(2) 1_555 1_555 1_555 yes
C(121) C(122) H(122) 119.64(3) 1_555 1_555 1_555 yes
C(123) C(122) H(122) 120.25(3) 1_555 1_555 1_555 yes
C(122) C(123) C(124) 119.28(2) 1_555 1_555 1_555 yes
C(122) C(123) H(123) 123.46(2) 1_555 1_555 1_555 yes
C(124) C(123) H(123) 117.25(3) 1_555 1_555 1_555 yes
N(125) C(124) C(123) 118.62(2) 1_555 1_555 1_555 yes
N(125) C(124) C(24) 117.05(2) 1_555 1_555 1_555 yes
C(123) C(124) C(24) 124.31(2) 1_555 1_555 1_555 yes
N(125) C(126) C(121) 118.63(2) 1_555 1_555 1_555 yes
N(125) C(126) C(26) 117.50(2) 1_555 1_555 1_555 yes
C(121) C(126) C(26) 123.87(2) 1_555 1_555 1_555 yes
C(124) C(24) H(24A) 112.30(2) 1_555 1_555 1_555 yes
C(124) C(24) H(24B) 110.01(2) 1_555 1_555 1_555 yes
C(124) C(24) H(24C) 110.25(2) 1_555 1_555 1_555 yes
H(24A) C(24) H(24B) 109.80(2) 1_555 1_555 1_555 yes
H(24A) C(24) H(24C) 108.98(2) 1_555 1_555 1_555 yes
H(24B) C(24) H(24C) 105.26(2) 1_555 1_555 1_555 yes
C(126) C(26) H(26A) 110.64(2) 1_555 1_555 1_555 yes
C(126) C(26) H(26B) 111.02(2) 1_555 1_555 1_555 yes
C(126) C(26) H(26C) 109.97(2) 1_555 1_555 1_555 yes
H(26A) C(26) H(26B) 106.25(3) 1_555 1_555 1_555 yes
H(26A) C(26) H(26C) 114.35(2) 1_555 1_555 1_555 yes
H(26B) C(26) H(26C) 104.39(2) 1_555 1_555 1_555 yes
CL(1) C(111) C(112) 118.505(17) 1_555 1_555 1_555 yes
CL(1) C(111) C(116) 118.810(17) 1_555 1_555 1_555 yes
C(112) C(111) C(116) 122.65(2) 1_555 1_555 1_555 yes
O(2) C(112) C(111) 124.94(2) 1_555 1_555 1_555 yes
O(3) C(113) C(114) 123.32(3) 1_555 1_555 1_555 yes
CL(2) C(114) C(113) 118.017(18) 1_555 1_555 1_555 yes
CL(2) C(114) C(115) 121.171(19) 1_555 1_555 1_555 yes
C(113) C(114) C(115) 120.81(2) 1_555 1_555 1_555 yes
O(5) C(115) C(114) 122.25(3) 1_555 1_555 1_555 yes
O(5) C(115) C(116) 116.09(2) 1_555 1_555 1_555 yes
C(114) C(115) C(116) 121.62(2) 1_555 1_555 1_555 yes
O(6) C(116) C(111) 125.30(3) 1_555 1_555 1_555 yes
O(6) C(116) C(115) 116.47(2) 1_555 1_555 1_555 yes
C(111) C(116) C(115) 118.22(2) 1_555 1_555 1_555 yes

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
H(5) O(5) C(115) C(114) -177.75(4) 1_555 1_555 1_555 1_555 yes
H(5) O(5) C(115) C(116) -0.23(2) 1_555 1_555 1_555 1_555 yes
C(124) N(125) C(126) C(121) -0.72(2) 1_555 1_555 1_555 1_555 yes
C(126) N(125) C(124) C(123) 0.09(2) 1_555 1_555 1_555 1_555 yes
C(126) N(125) C(124) C(24) 178.28(4) 1_555 1_555 1_555 1_555 yes
C(124) N(125) C(126) C(26) 179.50(4) 1_555 1_555 1_555 1_555 yes
H(125) N(125) C(124) C(123) -179.68(4) 1_555 1_555 1_555 1_555 yes
H(125) N(125) C(124) C(24) -1.50(2) 1_555 1_555 1_555 1_555 yes
H(125) N(125) C(126) C(121) 179.06(4) 1_555 1_555 1_555 1_555 yes
H(125) N(125) C(126) C(26) -0.72(2) 1_555 1_555 1_555 1_555 yes
C(122) C(121) C(126) N(125) 0.38(3) 1_555 1_555 1_555 1_555 yes
C(126) C(121) C(122) C(123) 0.55(3) 1_555 1_555 1_555 1_555 yes
C(122) C(121) C(126) C(26) -179.86(4) 1_555 1_555 1_555 1_555 yes
C(126) C(121) C(122) H(122) 179.73(4) 1_555 1_555 1_555 1_555 yes
H(121) C(121) C(122) C(123) 178.41(5) 1_555 1_555 1_555 1_555 yes
H(121) C(121) C(122) H(122) -2.41(3) 1_555 1_555 1_555 1_555 yes
H(121) C(121) C(126) N(125) -177.57(4) 1_555 1_555 1_555 1_555 yes
H(121) C(121) C(126) C(26) 2.19(2) 1_555 1_555 1_555 1_555 yes
C(121) C(122) C(123) C(124) -1.18(3) 1_555 1_555 1_555 1_555 yes
C(121) C(122) C(123) H(123) 179.83(5) 1_555 1_555 1_555 1_555 yes
H(122) C(122) C(123) C(124) 179.65(5) 1_555 1_555 1_555 1_555 yes
H(122) C(122) C(123) H(123) 0.65(3) 1_555 1_555 1_555 1_555 yes
C(122) C(123) C(124) N(125) 0.86(3) 1_555 1_555 1_555 1_555 yes
C(122) C(123) C(124) C(24) -177.18(4) 1_555 1_555 1_555 1_555 yes
H(123) C(123) C(124) N(125) 179.92(4) 1_555 1_555 1_555 1_555 yes
H(123) C(123) C(124) C(24) 1.88(2) 1_555 1_555 1_555 1_555 yes
N(125) C(124) C(24) H(24A) 56.22(3) 1_555 1_555 1_555 1_555 yes
N(125) C(124) C(24) H(24B) -66.40(3) 1_555 1_555 1_555 1_555 yes
N(125) C(124) C(24) H(24C) 177.95(3) 1_555 1_555 1_555 1_555 yes
C(123) C(124) C(24) H(24A) -125.71(4) 1_555 1_555 1_555 1_555 yes
C(123) C(124) C(24) H(24B) 111.68(3) 1_555 1_555 1_555 1_555 yes
C(123) C(124) C(24) H(24C) -3.98(2) 1_555 1_555 1_555 1_555 yes
N(125) C(126) C(26) H(26A) -64.06(3) 1_555 1_555 1_555 1_555 yes
N(125) C(126) C(26) H(26B) 53.65(3) 1_555 1_555 1_555 1_555 yes
N(125) C(126) C(26) H(26C) 168.67(3) 1_555 1_555 1_555 1_555 yes
C(121) C(126) C(26) H(26A) 116.18(4) 1_555 1_555 1_555 1_555 yes
C(121) C(126) C(26) H(26B) -126.11(4) 1_555 1_555 1_555 1_555 yes
C(121) C(126) C(26) H(26C) -11.10(2) 1_555 1_555 1_555 1_555 yes
CL(1) C(111) C(112) O(2) 4.68(2) 1_555 1_555 1_555 1_555 yes
CL(1) C(111) C(116) O(6) -0.47(2) 1_555 1_555 1_555 1_555 yes
CL(1) C(111) C(116) C(115) 178.14(3) 1_555 1_555 1_555 1_555 yes
C(116) C(111) C(112) O(2) -177.43(4) 1_555 1_555 1_555 1_555 yes
C(112) C(111) C(116) O(6) -178.35(4) 1_555 1_555 1_555 1_555 yes
C(112) C(111) C(116) C(115) 0.25(2) 1_555 1_555 1_555 1_555 yes
O(3) C(113) C(114) CL(2) 2.47(2) 1_555 1_555 1_555 1_555 yes
O(3) C(113) C(114) C(115) -178.08(4) 1_555 1_555 1_555 1_555 yes
CL(2) C(114) C(115) O(5) 0.30(2) 1_555 1_555 1_555 1_555 yes
CL(2) C(114) C(115) C(116) -177.09(3) 1_555 1_555 1_555 1_555 yes
C(113) C(114) C(115) O(5) -179.13(4) 1_555 1_555 1_555 1_555 yes
C(113) C(114) C(115) C(116) 3.48(2) 1_555 1_555 1_555 1_555 yes
O(5) C(115) C(116) O(6) -3.18(3) 1_555 1_555 1_555 1_555 yes
O(5) C(115) C(116) C(111) 178.10(3) 1_555 1_555 1_555 1_555 yes
C(114) C(115) C(116) O(6) 174.37(4) 1_555 1_555 1_555 1_555 yes
C(114) C(115) C(116) C(111) -4.36(2) 1_555 1_555 1_555 1_555 yes
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_(2,6)_neutron
_database_code_depnum_ccdc_archive 'CCDC 1478087'
_audit_update_record             
;
2016-05-04 deposited with the CCDC.
2016-06-13 downloaded from the CCDC.
;

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         
;
C6 H Cl2 O4, C7 H10 N 
;
_chemical_formula_sum            'C13 H11 Cl2 N O4'
_chemical_formula_weight         316.13
_chemical_compound_source        commercial

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.0071(3)
_cell_length_b                   9.0326(3)
_cell_length_c                   9.0768(3)
_cell_angle_alpha                93.526(2)
_cell_angle_beta                 104.359(2)
_cell_angle_gamma                110.821(2)
_cell_volume                     659.48(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7396
_cell_measurement_theta_min      3.134
_cell_measurement_theta_max      61.742
_cell_measurement_wavelength     0.9484

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          3
_exptl_crystal_size_mid          3
_exptl_crystal_size_min          2
_exptl_crystal_density_diffrn    1.592
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             194
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.1301
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.9484
_diffrn_radiation_probe          neutron
_diffrn_radiation_type           neutron
_diffrn_radiation_source         'nuclear reactor'

_diffrn_radiation_monochromator  Cu(220)
_diffrn_measurement_device_type  '4-circles Eulerian cradle'
_diffrn_measurement_method       'omega scans'
_diffrn_detector                 'multiwire proportional chamber'
_diffrn_detector_area_resol_mean 0.52
_diffrn_detector_details         
;
ILL cylindrically shaped large-area position sensitive detector 
with 120 by 30 deg detection angle (resolution: 0.4 by 0.64 pixels/mm)
;

_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.028
_diffrn_reflns_number            7399
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.134
_diffrn_reflns_theta_max         61.742
_diffrn_reflns_theta_full        34.683
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.835
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.835
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.835
_reflns_Friedel_coverage         0
_reflns_number_total             7396
_reflns_number_gt                6623
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'ILL-MAD software'
_computing_cell_refinement       'Dirax (Duisenberg, 1992)'
_computing_data_reduction        'PFIND, RETREAT (Wilkinson et al.,1988)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_atom_sites_solution_hydrogens   difmap

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0235P)²+0.6404P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0211(8)
_refine_ls_number_reflns         7396
_refine_ls_number_parameters     309
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0337
_refine_ls_wR_factor_ref         0.0808
_refine_ls_wR_factor_gt          0.0779
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_restrained_S_all      1.106
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.969
_refine_diff_density_min         -0.994
_refine_diff_density_rms         0.164

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_length_neutron
_atom_type_scat_source
C C 0.0000 0.0000 6.646 'Neutron Data Booklet Table 1.1-8'
H H 0.0000 0.0000 -3.739 'Neutron Data Booklet Table 1.1-8'
N N 0.0000 0.0000 9.36 'Neutron Data Booklet Table 1.1-8'
O O 0.0000 0.0000 5.803 'Neutron Data Booklet Table 1.1-8'
Cl Cl 0.0000 0.0000 9.577 'Neutron Data Booklet Table 1.1-8'

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 0.05988(4) 0.84850(4) 0.41655(4) 0.01400(5) Uani 1 1 d . . . . .
Cl2 Cl 0.29218(5) 0.26227(4) 0.41975(4) 0.01862(6) Uani 1 1 d . . . . .
O3 O 0.33001(7) 0.49421(7) 0.68715(6) 0.01636(9) Uani 1 1 d . . . . .
O2 O 0.20915(6) 0.72761(6) 0.69099(6) 0.01294(8) Uani 1 1 d . . . . .
O5 O 0.11143(7) 0.36111(6) 0.14777(6) 0.01494(8) Uani 1 1 d . . . . .
O6 O 0.02759(7) 0.61444(7) 0.14795(6) 0.01570(8) Uani 1 1 d . . . . .
N125 N 0.50663(3) 0.82725(4) 0.89766(3) 0.01138(5) Uani 1 1 d . . . . .
C121 C 0.77620(5) 1.02781(6) 0.95665(6) 0.01530(8) Uani 1 1 d . . . . .
C122 C 0.81932(5) 0.97047(6) 1.09369(6) 0.01741(8) Uani 1 1 d . . . . .
C123 C 0.70333(5) 0.83872(6) 1.12959(6) 0.01567(8) Uani 1 1 d . . . . .
C124 C 0.54331(5) 0.76740(5) 1.02875(5) 0.01184(7) Uani 1 1 d . . . . .
C126 C 0.61587(5) 0.95299(5) 0.85731(5) 0.01202(7) Uani 1 1 d . . . . .
C24 C 0.40597(5) 0.63054(6) 1.05760(6) 0.01509(7) Uani 1 1 d . . . . .
C26 C 0.55602(6) 1.00410(6) 0.70722(6) 0.01541(8) Uani 1 1 d . . . . .
C111 C 0.11499(5) 0.68341(5) 0.41976(5) 0.01067(6) Uani 1 1 d . . . . .
C112 C 0.18844(4) 0.65132(5) 0.56275(5) 0.01010(6) Uani 1 1 d . . . . .
C113 C 0.25392(5) 0.51435(5) 0.56356(5) 0.01115(6) Uani 1 1 d . . . . .
C114 C 0.22366(5) 0.41756(5) 0.41717(5) 0.01218(7) Uani 1 1 d . . . . .
C115 C 0.14273(5) 0.44833(5) 0.28271(5) 0.01129(6) Uani 1 1 d . . . . .
C116 C 0.08886(5) 0.58935(5) 0.27810(5) 0.01090(6) Uani 1 1 d . . . . .
H5 H 0.05798(16) 0.40600(16) 0.06348(14) 0.0282(2) Uani 1 1 d . . . . .
H121 H 0.86482(15) 1.12994(17) 0.92597(18) 0.0328(3) Uani 1 1 d . . . . .
H122 H 0.94407(15) 1.0297(2) 1.17323(19) 0.0384(3) Uani 1 1 d . . . . .
H123 H 0.73456(17) 0.7905(2) 1.23470(17) 0.0343(3) Uani 1 1 d . . . . .
H125 H 0.38407(12) 0.77096(14) 0.82002(13) 0.02294(17) Uani 1 1 d . . . . .
H24A H 0.3490(2) 0.53355(19) 0.9596(2) 0.0448(4) Uani 1 1 d . . . . .
H24B H 0.3076(2) 0.6687(2) 1.0707(3) 0.0454(4) Uani 1 1 d . . . . .
H24C H 0.4515(2) 0.5859(2) 1.1603(2) 0.0442(4) Uani 1 1 d . . . . .
H26A H 0.5150(9) 0.9048(7) 0.6118(8) 0.0427(12) Uani 0.63(3) 1 d . . P A 1
H26B H 0.4473(9) 1.0287(10) 0.7020(8) 0.0454(14) Uani 0.63(3) 1 d . . P A 1
H26C H 0.6514(11) 1.1060(14) 0.6892(15) 0.058(2) Uani 0.63(3) 1 d . . P A 1
H26D H 0.558(4) 0.933(3) 0.6137(13) 0.064(4) Uani 0.37(3) 1 d . . P A 2
H26E H 0.637(2) 1.122(2) 0.705(3) 0.067(5) Uani 0.37(3) 1 d . . P A 2
H26F H 0.4317(11) 1.001(2) 0.6875(18) 0.055(3) Uani 0.37(3) 1 d . . P A 2



#----------------------------------------------------------------------------#
#                   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 C111 1.7307(5) . ?
Cl2 C114 1.7208(6) . ?
O3 C113 1.2221(7) . ?
O2 C112 1.2518(6) . ?
O5 C115 1.3238(6) . ?
O5 H5 0.9878(14) . ?
O6 C116 1.2449(7) . ?
N125 C126 1.3520(5) . ?
N125 C124 1.3521(6) . ?
N125 H125 1.0699(10) . ?
C121 C126 1.3930(6) . ?
C121 C122 1.3962(8) . ?
C121 H121 1.0881(13) . ?
C122 C123 1.3952(7) . ?
C122 H122 1.0921(12) . ?
C123 C124 1.3940(6) . ?
C123 H123 1.0884(15) . ?
C124 C24 1.4968(6) . ?
C126 C26 1.4999(7) . ?
C24 H24A 1.0863(15) . ?
C24 H24B 1.0874(15) . ?
C24 H24C 1.0837(17) . ?
C26 H26A 1.096(5) . ?
C26 H26B 1.070(4) . ?
C26 H26C 1.067(8) . ?
C26 H26D 1.038(9) . ?
C26 H26E 1.060(12) . ?
C26 H26F 1.079(10) . ?
C111 C112 1.4010(6) . ?
C111 C116 1.4156(5) . ?
C112 C113 1.5480(6) . ?
C113 C114 1.4534(6) . ?
C114 C115 1.3575(7) . ?
C115 C116 1.5151(6) . ?

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
C115 O5 H5 110.27(9) . . ?
C126 N125 C124 124.09(3) . . ?
C126 N125 H125 117.71(7) . . ?
C124 N125 H125 118.20(7) . . ?
C126 C121 C122 119.23(4) . . ?
C126 C121 H121 119.29(9) . . ?
C122 C121 H121 121.48(9) . . ?
C123 C122 C121 120.21(4) . . ?
C123 C122 H122 120.06(10) . . ?
C121 C122 H122 119.73(10) . . ?
C124 C123 C122 119.26(5) . . ?
C124 C123 H123 119.14(9) . . ?
C122 C123 H123 121.60(8) . . ?
N125 C124 C123 118.57(4) . . ?
N125 C124 C24 117.08(3) . . ?
C123 C124 C24 124.32(4) . . ?
N125 C126 C121 118.63(4) . . ?
N125 C126 C26 117.56(3) . . ?
C121 C126 C26 123.82(4) . . ?
C124 C24 H24A 110.94(10) . . ?
C124 C24 H24B 110.17(10) . . ?
H24A C24 H24B 105.79(17) . . ?
C124 C24 H24C 110.76(10) . . ?
H24A C24 H24C 109.59(17) . . ?
H24B C24 H24C 109.48(17) . . ?
C126 C26 H26A 110.0(4) . . ?
C126 C26 H26B 111.3(4) . . ?
H26A C26 H26B 104.1(5) . . ?
C126 C26 H26C 110.9(7) . . ?
H26A C26 H26C 109.8(8) . . ?
H26B C26 H26C 110.6(8) . . ?
C126 C26 H26D 112.2(7) . . ?
C126 C26 H26E 110.0(11) . . ?
H26D C26 H26E 104.7(17) . . ?
C126 C26 H26F 112.3(7) . . ?
H26D C26 H26F 108.1(12) . . ?
H26E C26 H26F 109.1(14) . . ?
C112 C111 C116 122.69(4) . . ?
C112 C111 Cl1 118.45(3) . . ?
C116 C111 Cl1 118.83(4) . . ?
O2 C112 C111 125.02(4) . . ?
O2 C112 C113 116.97(4) . . ?
C111 C112 C113 117.99(3) . . ?
O3 C113 C114 123.33(4) . . ?
O3 C113 C112 118.31(4) . . ?
C114 C113 C112 118.36(4) . . ?
C115 C114 C113 120.86(4) . . ?
C115 C114 Cl2 121.13(3) . . ?
C113 C114 Cl2 118.01(4) . . ?
O5 C115 C114 122.29(5) . . ?
O5 C115 C116 116.03(4) . . ?
C114 C115 C116 121.64(4) . . ?
O6 C116 C111 125.36(5) . . ?
O6 C116 C115 116.45(4) . . ?
C111 C116 C115 118.18(4) . . ?

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
C126 C121 C122 C123 0.63(7) . . . . ?
C121 C122 C123 C124 -1.33(8) . . . . ?
C126 N125 C124 C123 0.01(6) . . . . ?
C126 N125 C124 C24 178.29(4) . . . . ?
C122 C123 C124 N125 1.01(7) . . . . ?
C122 C123 C124 C24 -177.14(5) . . . . ?
C124 N125 C126 C121 -0.71(6) . . . . ?
C124 N125 C126 C26 179.55(4) . . . . ?
C122 C121 C126 N125 0.37(7) . . . . ?
C122 C121 C126 C26 -179.91(4) . . . . ?
C116 C111 C112 O2 -177.52(4) . . . . ?
Cl1 C111 C112 O2 4.47(6) . . . . ?
C116 C111 C112 C113 4.28(6) . . . . ?
Cl1 C111 C112 C113 -173.72(3) . . . . ?
O2 C112 C113 O3 -4.17(6) . . . . ?
C111 C112 C113 O3 174.17(5) . . . . ?
O2 C112 C113 C114 176.61(4) . . . . ?
C111 C112 C113 C114 -5.05(5) . . . . ?
O3 C113 C114 C115 -177.96(5) . . . . ?
C112 C113 C114 C115 1.22(6) . . . . ?
O3 C113 C114 Cl2 2.49(7) . . . . ?
C112 C113 C114 Cl2 -178.33(3) . . . . ?
C113 C114 C115 O5 -179.12(4) . . . . ?
Cl2 C114 C115 O5 0.42(6) . . . . ?
C113 C114 C115 C116 3.36(6) . . . . ?
Cl2 C114 C115 C116 -177.11(3) . . . . ?
C112 C111 C116 O6 -178.37(5) . . . . ?
Cl1 C111 C116 O6 -0.37(6) . . . . ?
C112 C111 C116 C115 0.12(6) . . . . ?
Cl1 C111 C116 C115 178.11(3) . . . . ?
O5 C115 C116 O6 -3.28(6) . . . . ?
C114 C115 C116 O6 174.40(4) . . . . ?
O5 C115 C116 C111 178.10(4) . . . . ?
C114 C115 C116 C111 -4.22(6) . . . . ?

####################################################################### 
# 
# 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_2_(2,6)_shelx
_database_code_depnum_ccdc_archive 'CCDC 1478088'
_audit_update_record             
;
2016-05-04 deposited with the CCDC.
2016-06-13 downloaded from the CCDC.
;

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         
;
C6 Cl2 O4, 2(C7 H10 N)  
;
_chemical_formula_sum            'C20 H20 Cl2 N2 O4'
_chemical_formula_weight         423.28
_chemical_compound_source        commercial

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14

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

_cell_length_a                   7.1427(3)
_cell_length_b                   9.3025(4)
_cell_length_c                   14.7753(6)
_cell_angle_alpha                90
_cell_angle_beta                 94.526(2)
_cell_angle_gamma                90
_cell_volume                     978.68(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    11814
_cell_measurement_theta_min      1
_cell_measurement_theta_max      53.43
_cell_measurement_wavelength     0.71073


#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             440
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.361
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4471
_exptl_absorpt_correction_T_max  0.751
_exptl_absorpt_process_details   'SADABS, Bruker(2001)'
#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'APEX-II CCD'
_diffrn_orient_matrix_type       'x-axis to radiation source'
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'φ or ω oscillation scans'
_diffrn_reflns_av_R_equivalents  0.0799
_diffrn_reflns_av_unetI/netI     0.0466
_diffrn_reflns_number            11814
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.59
_diffrn_reflns_theta_max         53.43
_diffrn_reflns_theta_full        53.43
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_reflns_number_total             11814
_reflns_number_gt                8736
_reflns_threshold_expression     >2σ(I)
_diffrn_reflns_reduction_process 
;
 Scaled and merged with Sortav
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0574P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         11814
_refine_ls_number_parameters     167
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0348
_refine_ls_wR_factor_ref         0.1011
_refine_ls_wR_factor_gt          0.0939
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.69
_refine_diff_density_min         -0.3
_refine_diff_density_rms         0.083

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.596186(14) 0.367867(11) 1.196525(6) 0.01536(2) Uani 1 1 d . . .
O2 O 0.68273(5) 0.24435(4) 1.01852(2) 0.01765(5) Uani 1 1 d . . .
O3 O 0.59113(5) 0.35145(3) 0.85291(2) 0.01589(5) Uani 1 1 d . . .
N125 N 0.89832(5) 0.13001(4) 0.89990(2) 0.01346(4) Uani 1 1 d . . .
C121 C 1.02005(7) -0.08309(5) 0.84123(3) 0.01914(6) Uani 1 1 d . . .
C122 C 1.17376(7) -0.00566(6) 0.81517(3) 0.02135(7) Uani 1 1 d . . .
C123 C 1.18680(6) 0.14129(6) 0.83258(4) 0.02065(7) Uani 1 1 d . . .
C124 C 1.04622(5) 0.20877(5) 0.87665(3) 0.01600(5) Uani 1 1 d . . .
C126 C 0.87925(6) -0.01237(4) 0.88341(3) 0.01477(5) Uani 1 1 d . . .
C24 C 1.04953(8) 0.36444(5) 0.90221(4) 0.02338(8) Uani 1 1 d . . .
C26 C 0.70508(7) -0.08319(6) 0.91129(4) 0.02244(8) Uani 1 1 d . . .
C111 C 0.53807(5) 0.43740(4) 1.08883(2) 0.01160(4) Uani 1 1 d . . .
C112 C 0.59504(5) 0.36181(4) 1.01392(2) 0.01156(4) Uani 1 1 d . . .
C113 C 0.54894(5) 0.42559(4) 0.91825(2) 0.01104(4) Uani 1 1 d . . .
H121 H 1.0126(16) -0.1875(14) 0.8308(8) 0.033(3) Uiso 1 1 d . . .
H122 H 1.2727(16) -0.0535(14) 0.7835(9) 0.034(3) Uiso 1 1 d . . .
H123 H 1.2915(16) 0.1938(15) 0.8144(9) 0.040(3) Uiso 1 1 d . . .
H125 H 0.8112(15) 0.1729(14) 0.9333(9) 0.033(3) Uiso 1 1 d . . .
H24A H 1.1357(18) 0.4113(15) 0.8714(10) 0.044(3) Uiso 1 1 d . . .
H24B H 1.075(2) 0.3761(13) 0.9636(11) 0.044(4) Uiso 1 1 d . . .
H24C H 0.9373(17) 0.4057(14) 0.8829(9) 0.033(3) Uiso 1 1 d . . .
H26A H 0.662(2) -0.041(2) 0.9625(12) 0.061(4) Uiso 1 1 d . . .
H26B H 0.611(2) -0.0747(18) 0.8653(11) 0.061(4) Uiso 1 1 d . . .
H26C H 0.7208(17) -0.1895(16) 0.9208(9) 0.040(3) Uiso 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 C111 1.7374(3) . ?
O2 C112 1.2586(5) . ?
O3 C113 1.2428(4) . ?
N125 C126 1.3516(5) . ?
N125 C124 1.3521(5) . ?
N125 H125 0.916(12) . ?
C121 C126 1.3898(6) . ?
C121 C122 1.3926(8) . ?
C121 H121 0.984(13) . ?
C122 C123 1.3927(8) . ?
C122 H122 0.984(12) . ?
C123 C124 1.3891(6) . ?
C123 H123 0.950(13) . ?
C124 C24 1.4962(7) . ?
C126 C26 1.4941(6) . ?
C24 H24A 0.906(14) . ?
C24 H24B 0.918(16) . ?
C24 H24C 0.914(12) . ?
C26 H26A 0.924(17) . ?
C26 H26B 0.919(16) . ?
C26 H26C 1.004(15) . ?
C111 C112 1.3987(5) . ?
C111 C113 1.4182(5) 3_667 ?
C112 C113 1.5443(5) . ?
C113 C111 1.4182(5) 3_667 ?

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
C126 N125 C124 123.70(3) . . ?
C126 N125 H125 117.4(8) . . ?
C124 N125 H125 118.6(8) . . ?
C126 C121 C122 119.56(4) . . ?
C126 C121 H121 120.4(7) . . ?
C122 C121 H121 120.1(7) . . ?
C121 C122 C123 119.96(4) . . ?
C121 C122 H122 120.6(8) . . ?
C123 C122 H122 119.4(8) . . ?
C124 C123 C122 119.33(4) . . ?
C124 C123 H123 120.9(8) . . ?
C122 C123 H123 119.7(8) . . ?
N125 C124 C123 118.84(4) . . ?
N125 C124 C24 117.22(4) . . ?
C123 C124 C24 123.92(4) . . ?
N125 C126 C121 118.59(4) . . ?
N125 C126 C26 117.17(4) . . ?
C121 C126 C26 124.24(4) . . ?
C124 C24 H24A 109.7(9) . . ?
C124 C24 H24B 111.2(8) . . ?
H24A C24 H24B 110.4(12) . . ?
C124 C24 H24C 109.4(8) . . ?
H24A C24 H24C 104.8(12) . . ?
H24B C24 H24C 111.2(12) . . ?
C126 C26 H26A 112.3(10) . . ?
C126 C26 H26B 109.4(10) . . ?
H26A C26 H26B 107.4(13) . . ?
C126 C26 H26C 112.7(7) . . ?
H26A C26 H26C 109.9(14) . . ?
H26B C26 H26C 104.7(12) . . ?
C112 C111 C113 123.13(3) . 3_667 ?
C112 C111 Cl1 118.31(3) . . ?
C113 C111 Cl1 118.28(2) 3_667 . ?
O2 C112 C111 124.63(3) . . ?
O2 C112 C113 116.89(3) . . ?
C111 C112 C113 118.48(3) . . ?
O3 C113 C111 124.97(3) . 3_667 ?
O3 C113 C112 116.78(3) . . ?
C111 C113 C112 118.26(3) 3_667 . ?

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
C126 C121 C122 C123 0.88(7) . . . . ?
C121 C122 C123 C124 0.55(8) . . . . ?
C126 N125 C124 C123 0.59(6) . . . . ?
C126 N125 C124 C24 -178.16(4) . . . . ?
C122 C123 C124 N125 -1.28(7) . . . . ?
C122 C123 C124 C24 177.38(5) . . . . ?
C124 N125 C126 C121 0.84(6) . . . . ?
C124 N125 C126 C26 -178.52(4) . . . . ?
C122 C121 C126 N125 -1.56(6) . . . . ?
C122 C121 C126 C26 177.75(4) . . . . ?
C113 C111 C112 O2 175.44(4) 3_667 . . . ?
Cl1 C111 C112 O2 1.60(5) . . . . ?
C113 C111 C112 C113 -4.32(6) 3_667 . . . ?
Cl1 C111 C112 C113 -178.17(2) . . . . ?
O2 C112 C113 O3 4.56(5) . . . . ?
C111 C112 C113 O3 -175.66(3) . . . . ?
O2 C112 C113 C111 -175.67(4) . . . 3_667 ?
C111 C112 C113 C111 4.11(5) . . . 3_667 ?

####################################################################### 
# 
# 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_2_(2,6)_xd
_database_code_depnum_ccdc_archive 'CCDC 1478089'
_audit_update_record             
;
2016-05-04 deposited with the CCDC.
2016-06-13 downloaded from the CCDC.
;

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         
;
C6 Cl2 O4, 2(C7 H10 N)  
;
_chemical_formula_sum            'C20 H20 Cl2 N2 O4'
_chemical_formula_weight         423.28
_chemical_compound_source        commercial

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14

loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,1/2-Y,1/2+Z

_cell_length_a                   7.140(5)
_cell_length_b                   9.290(5)
_cell_length_c                   14.774(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 94.463(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     977.0(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    11814
_cell_measurement_theta_min      1
_cell_measurement_theta_max      53.43
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             440
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.361
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4471
_exptl_absorpt_correction_T_max  0.751
_exptl_absorpt_process_details   'SADABS, Bruker(2001)'
#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'APEX-II CCD'
_diffrn_orient_matrix_type       'x-axis to radiation source'
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'φ or ω oscillation scans'
_diffrn_reflns_av_R_equivalents  0.0799
_diffrn_reflns_av_unetI/netI     0.0466
_diffrn_reflns_number            11814
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.59
_diffrn_reflns_theta_max         53.43
_diffrn_reflns_theta_full        53.43
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_reflns_number_total             11814
_reflns_number_gt                8736
_reflns_threshold_expression     >2σ(I)
_diffrn_reflns_reduction_process 
;
 Scaled and merged with Sortav
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
        ?
;
_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
        calc w1 = 1/[s²(Fo)]
;
_refine_ls_extinction_method     none
_refine_ls_number_reflns         9143
_refine_ls_number_parameters     378
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.06
_refine_ls_R_factor_gt           0.028
_refine_ls_wR_factor_ref         0.026
_refine_ls_goodness_of_fit_ref   1.155
_refine_ls_shift/su_max          0.00001
_refine_diff_density_max         0.367
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.061


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, 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_symmetry_multiplicity
Cl(1) Cl 0.596207(11) 0.367893(9) 1.196532(4) 0.015 Uani 1 4
O(2) O 0.68256(6) 0.24439(5) 1.01857(3) 0.017 Uani 1 4
O(3) O 0.59116(6) 0.35130(4) 0.85300(2) 0.016 Uani 1 4
N(125) N 0.89828(4) 0.12990(4) 0.89994(2) 0.013 Uani 1 4
C(121) C 1.02002(6) -0.08324(4) 0.84118(3) 0.019 Uani 1 4
C(122) C 1.17406(6) -0.00573(6) 0.81507(3) 0.021 Uani 1 4
C(123) C 1.18690(5) 0.14149(5) 0.83251(3) 0.021 Uani 1 4
C(124) C 1.04613(5) 0.20875(4) 0.87666(2) 0.016 Uani 1 4
C(126) C 0.87921(5) -0.01238(4) 0.88343(2) 0.015 Uani 1 4
C(24) C 1.04950(6) 0.36438(5) 0.90220(4) 0.023 Uani 1 4
C(26) C 0.70527(6) -0.08323(5) 0.91122(3) 0.022 Uani 1 4
C(111) C 0.53812(4) 0.43740(3) 1.088890(18) 0.011 Uani 1 4
C(112) C 0.59493(4) 0.36179(3) 1.013926(18) 0.011 Uani 1 4
C(113) C 0.54900(4) 0.42563(3) 0.918275(18) 0.011 Uani 1 4
H(121) H 1.011827 -0.199134 0.829615 0.035 Uani 1 4
H(122) H 1.284337 -0.059085 0.779787 0.037 Uani 1 4
H(123) H 1.307055 0.20167 0.81173 0.038 Uani 1 4
H(125) H 0.795575 0.180565 0.93932 0.027 Uani 1 4
H(24A) H 1.152385 0.420408 0.865385 0.042 Uani 1 4
H(24B) H 1.079683 0.378059 0.973626 0.038 Uani 1 4
H(24C) H 0.917096 0.413107 0.879462 0.036 Uani 1 4
H(26A) H 0.655249 -0.034967 0.970362 0.038 Uani 1 4
H(26B) H 0.595758 -0.073335 0.85758 0.039 Uani 1 4
H(26C) H 0.721322 -0.193179 0.921129 0.043 Uani 1 4



#----------------------------------------------------------------------------#
#                   MULTIPOLE PARAMETERS                                     #
#----------------------------------------------------------------------------#

loop_
_atom_rho_multipole_atom_label
_atom_rho_multipole_coeff_Pv
_atom_rho_multipole_coeff_P00
_atom_rho_multipole_coeff_P11
_atom_rho_multipole_coeff_P1-1
_atom_rho_multipole_coeff_P10
_atom_rho_multipole_coeff_P20
_atom_rho_multipole_coeff_P21
_atom_rho_multipole_coeff_P2-1
_atom_rho_multipole_coeff_P22
_atom_rho_multipole_coeff_P2-2
_atom_rho_multipole_coeff_P30
_atom_rho_multipole_coeff_P31
_atom_rho_multipole_coeff_P3-1
_atom_rho_multipole_coeff_P32
_atom_rho_multipole_coeff_P3-2
_atom_rho_multipole_coeff_P33
_atom_rho_multipole_coeff_P3-3
_atom_rho_multipole_coeff_P40
_atom_rho_multipole_coeff_P41
_atom_rho_multipole_coeff_P4-1
_atom_rho_multipole_coeff_P42
_atom_rho_multipole_coeff_P4-2
_atom_rho_multipole_coeff_P43
_atom_rho_multipole_coeff_P4-3
_atom_rho_multipole_coeff_P44
_atom_rho_multipole_coeff_P4-4
_atom_rho_multipole_kappa
_atom_rho_multipole_kappa_prime0
_atom_rho_multipole_kappa_prime1
_atom_rho_multipole_kappa_prime2
_atom_rho_multipole_kappa_prime3
_atom_rho_multipole_kappa_prime4
Cl(1) 7.29(3) 0 -0.058(13) 0.133(13) -0.017(14) -0.156(17) -0.096(16)
-0.027(16) 0.022(14) -0.002(17) 0.042(11) -0.039(10) 0.022(10) 0.002(10)
-0.016(11) -0.022(10) 0.008(10) 0.052(14) -0.013(13) 0.000(13) -0.004(13)
-0.009(13) -0.001(14) 0.011(13) 0.000(13) 0.021(13) 1.014917 1 1 1 1 1
O(2) 6.17(2) 0 0.029(12) 0.035(10) -0.060(11) -0.028(12) -0.018(12) 0.020(10)
-0.035(11) -0.077(11) 0.013(9) -0.019(9) -0.006(8) 0.041(9) -0.005(9) -0.001(9)
0.046(9) 0 0 0 0 0 0 0 0 0 0.994336 1.014256 1.014256 1.014256 1.014256
1.014256
O(3) 6.17(2) 0 -0.006(11) -0.066(10) -0.013(10) -0.003(11) -0.019(11) 0.006(11)
-0.099(11) -0.030(11) 0.034(9) -0.001(8) -0.003(8) 0.032(9) 0.003(9) -0.016(9)
0.023(9) 0 0 0 0 0 0 0 0 0 0.994336 1.014256 1.014256 1.014256 1.014256
1.014256
N(125) 4.97(3) 0 0.037(13) -0.044(13) 0.003(11) -0.066(12) -0.022(12)
-0.015(11) -0.012(12) 0.005(13) 0.009(12) 0.002(11) 0.028(11) -0.003(11)
0.014(11) 0.186(11) 0.011(12) 0 0 0 0 0 0 0 0 0 1.000034 0.95724 0.95724
0.95724 0.95724 0.95724
C(121) 4.02(4) 0 0.015(19) 0.105(17) 0.033(15) -0.179(16) 0.011(16) 0.022(14)
-0.014(16) 0.000(17) -0.063(17) 0.050(16) 0.010(15) 0.009(16) -0.023(16)
0.225(17) 0.014(18) 0 0 0 0 0 0 0 0 0 1.000465 0.980537 0.980537 0.980537
0.980537 0.980537
C(122) 3.98(4) 0 0.044(19) 0.068(18) -0.009(16) -0.204(17) 0.024(16) 0.005(15)
0.021(17) -0.025(18) -0.012(18) 0.015(17) 0.046(16) -0.010(17) -0.034(17)
0.285(19) -0.019(19) 0 0 0 0 0 0 0 0 0 1.000465 0.980537 0.980537 0.980537
0.980537 0.980537
C(123) 4.07(4) 0 0.015(19) 0.036(18) -0.012(17) -0.172(17) 0.030(16) 0.054(15)
0.013(18) -0.005(16) -0.008(18) -0.014(17) 0.038(16) 0.050(17) 0.007(16)
0.254(17) -0.007(18) 0 0 0 0 0 0 0 0 0 1.000465 0.980537 0.980537 0.980537
0.980537 0.980537
C(124) 4.07(4) 0 -0.040(16) 0.031(17) 0.008(15) -0.193(15) -0.021(14)
-0.012(14) -0.059(15) -0.014(15) 0.005(16) -0.001(15) 0.041(15) 0.042(16)
-0.020(16) 0.269(16) 0.024(17) 0 0 0 0 0 0 0 0 0 1.000465 0.980537 0.980537
0.980537 0.980537 0.980537
C(126) 4.11(4) 0 0.005(16) 0.026(16) 0.004(14) -0.214(14) -0.017(13) -0.012(14)
-0.008(15) -0.025(14) -0.017(16) -0.034(15) 0.038(14) 0.008(15) -0.013(15)
0.289(16) 0.020(16) 0 0 0 0 0 0 0 0 0 1.000465 0.980537 0.980537 0.980537
0.980537 0.980537
C(24) 4.39(6) 0 -0.118(19) -0.002(19) 0.017(18) 0.021(17) -0.011(17) -0.111(16)
-0.061(16) 0.006(18) 0.20(2) -0.129(19) -0.040(18) -0.007(19) 0.053(19)
0.051(19) -0.214(19) 0 0 0 0 0 0 0 0 0 0.988898 0.915326 0.915326 0.915326
0.915326 0.915326
C(26) 4.49(7) 0 0.013(19) 0.107(19) 0.074(19) 0.052(18) -0.026(17) 0.041(17)
-0.028(17) -0.076(17) 0.15(2) 0.023(18) 0.094(19) -0.092(18) -0.165(18) 0.03(2)
-0.234(19) 0 0 0 0 0 0 0 0 0 0.988898 0.915326 0.915326 0.915326 0.915326
0.915326
C(111) 4.13(4) 0 0.064(15) -0.059(15) 0.012(14) -0.046(13) 0.022(13) -0.031(12)
0.032(14) 0.063(14) -0.005(15) 0.008(14) -0.025(14) 0.033(14) -0.020(15)
0.249(15) -0.034(15) 0 0 0 0 0 0 0 0 0 0.998526 0.965829 0.965829 0.965829
0.965829 0.965829
C(112) 4.07(4) 0 -0.006(15) -0.036(15) 0.038(14) -0.256(14) -0.061(13)
-0.010(13) -0.033(14) 0.021(14) 0.015(15) 0.009(14) 0.031(14) -0.003(15)
0.026(15) 0.322(15) 0.049(16) 0 0 0 0 0 0 0 0 0 0.998526 0.965829 0.965829
0.965829 0.965829 0.965829
C(113) 4.17(3) 0 0.045(15) -0.041(15) 0.014(13) -0.247(13) 0.013(12) -0.035(12)
0.064(14) 0.060(14) -0.033(15) -0.010(14) 0.007(14) 0.006(14) 0.008(15)
0.284(15) -0.001(16) 0 0 0 0 0 0 0 0 0 0.998526 0.965829 0.965829 0.965829
0.965829 0.965829
H(121) 0.855(16) 0 0.001(10) -0.026(10) 0.208(12) 0.141(15) 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0 0 1.173039 1.173039 1.173039 1.173039 1.173039 1.173039
H(122) 0.855(16) 0 0.001(10) -0.026(10) 0.208(12) 0.141(15) 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0 0 1.173039 1.173039 1.173039 1.173039 1.173039 1.173039
H(123) 0.855(16) 0 0.001(10) -0.026(10) 0.208(12) 0.141(15) 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0 0 1.173039 1.173039 1.173039 1.173039 1.173039 1.173039
H(125) 0.74(2) 0 0.013(15) -0.011(16) 0.131(17) 0.26(2) 0 0 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 1.173039 1.173039 1.173039 1.173039 1.173039 1.173039
H(24A) 0.798(18) 0 -0.015(12) -0.006(11) 0.129(12) 0.011(16) 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0 0 0 1.140035 1.140035 1.140035 1.140035 1.140035 1.140035
H(24B) 0.798(18) 0 -0.015(12) -0.006(11) 0.129(12) 0.011(16) 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0 0 0 1.140035 1.140035 1.140035 1.140035 1.140035 1.140035
H(24C) 0.798(18) 0 -0.015(12) -0.006(11) 0.129(12) 0.011(16) 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0 0 0 1.140035 1.140035 1.140035 1.140035 1.140035 1.140035
H(26A) 0.738(18) 0 0.020(12) -0.032(11) 0.091(13) -0.008(17) 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0 0 0 1.140035 1.140035 1.140035 1.140035 1.140035 1.140035
H(26B) 0.738(18) 0 0.020(12) -0.032(11) 0.091(13) -0.008(17) 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0 0 0 1.140035 1.140035 1.140035 1.140035 1.140035 1.140035
H(26C) 0.738(18) 0 0.020(12) -0.032(11) 0.091(13) -0.008(17) 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0 0 0 1.140035 1.140035 1.140035 1.140035 1.140035 1.140035

loop_
_atom_local_axes_atom_label
_atom_local_axes_atom0
_atom_local_axes_ax1
_atom_local_axes_atom1
_atom_local_axes_atom2
_atom_local_axes_ax2
CL(1) C(111) Z CL(1) C(112) Y
O(2) C(112) Z O(2) H(125) Y
O(3) C(113) Z O(3) C(112) Y
N(125) C(124) X N(125) C(126) Y
C(121) C(122) X C(121) C(126) Y
C(122) C(121) X C(122) C(123) Y
C(123) C(122) X C(123) C(124) Y
C(124) N(125) X C(124) C(123) Y
C(126) N(125) X C(126) C(121) Y
C(24) H(24A) Z C(24) H(24C) Y
C(26) H(26B) Z C(26) H(26A) Y
C(111) C(112) X C(111) CL(1) Y
C(112) C(113) X C(112) C(111) Y
C(113) O(3) X C(113) C(112) Y
H(121) C(121) Z H(121) C(122) Y
H(122) C(122) Z H(122) C(123) Y
H(123) C(123) Z H(123) C(122) Y
H(125) N(125) Z H(125) O(2) Y
H(24A) C(24) Z H(24A) H(24C) Y
H(24B) C(24) Z H(24B) H(24A) Y
H(24C) C(24) Z H(24C) H(24A) Y
H(26A) C(26) Z H(26A) H(26B) Y
H(26B) C(26) Z H(26B) H(26A) Y
H(26C) C(26) Z H(26C) H(26B) Y


#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
CL(1) C(111) 1.7365(3) 1_555 1_555 yes
O(2) C(112) 1.2566(5) 1_555 1_555 yes
O(3) C(113) 1.2421(4) 1_555 1_555 yes
N(125) C(124) 1.3512(5) 1_555 1_555 yes
N(125) C(126) 1.3491(5) 1_555 1_555 yes
N(125) H(125) 1.0790(3) 1_555 1_555 yes
C(121) C(122) 1.3939(7) 1_555 1_555 yes
C(121) C(126) 1.3897(5) 1_555 1_555 yes
C(121) H(121) 1.0910(4) 1_555 1_555 yes
C(122) C(123) 1.3935(7) 1_555 1_555 yes
C(122) H(122) 1.0960(4) 1_555 1_555 yes
C(123) C(124) 1.3886(5) 1_555 1_555 yes
C(123) H(123) 1.0880(4) 1_555 1_555 yes
C(124) C(24) 1.4940(6) 1_555 1_555 yes
C(126) C(26) 1.4911(5) 1_555 1_555 yes
C(24) H(24A) 1.0810(5) 1_555 1_555 yes
C(24) H(24B) 1.0680(5) 1_555 1_555 yes
C(24) H(24C) 1.0780(5) 1_555 1_555 yes
C(26) H(26A) 1.0680(5) 1_555 1_555 yes
C(26) H(26B) 1.0730(5) 1_555 1_555 yes
C(26) H(26C) 1.0370(4) 1_555 1_555 yes
C(111) C(112) 1.3980(4) 1_555 1_555 yes
C(111) C(113) 1.4166(4) 1_555 3_667 yes

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C(124) N(125) C(126) 123.71(3) 1_555 1_555 1_555 yes
C(124) N(125) H(125) 118.55(3) 1_555 1_555 1_555 yes
C(126) N(125) H(125) 117.49(3) 1_555 1_555 1_555 yes
C(122) C(121) C(126) 119.58(4) 1_555 1_555 1_555 yes
C(122) C(121) H(121) 120.01(4) 1_555 1_555 1_555 yes
C(126) C(121) H(121) 120.40(4) 1_555 1_555 1_555 yes
C(121) C(122) C(123) 119.86(3) 1_555 1_555 1_555 yes
C(121) C(122) H(122) 120.64(4) 1_555 1_555 1_555 yes
C(123) C(122) H(122) 119.50(4) 1_555 1_555 1_555 yes
C(122) C(123) C(124) 119.27(4) 1_555 1_555 1_555 yes
C(122) C(123) H(123) 119.62(4) 1_555 1_555 1_555 yes
C(124) C(123) H(123) 121.12(4) 1_555 1_555 1_555 yes
N(125) C(124) C(123) 118.95(4) 1_555 1_555 1_555 yes
N(125) C(124) C(24) 117.25(3) 1_555 1_555 1_555 yes
C(123) C(124) C(24) 123.79(4) 1_555 1_555 1_555 yes
N(125) C(126) C(121) 118.61(3) 1_555 1_555 1_555 yes
N(125) C(126) C(26) 117.21(3) 1_555 1_555 1_555 yes
C(121) C(126) C(26) 124.17(4) 1_555 1_555 1_555 yes
C(124) C(24) H(24A) 109.70(4) 1_555 1_555 1_555 yes
C(124) C(24) H(24B) 111.27(4) 1_555 1_555 1_555 yes
C(124) C(24) H(24C) 109.34(3) 1_555 1_555 1_555 yes
H(24A) C(24) H(24B) 110.31(4) 1_555 1_555 1_555 yes
H(24A) C(24) H(24C) 104.76(4) 1_555 1_555 1_555 yes
H(24B) C(24) H(24C) 111.26(4) 1_555 1_555 1_555 yes
C(126) C(26) H(26A) 112.25(4) 1_555 1_555 1_555 yes
C(126) C(26) H(26B) 109.48(4) 1_555 1_555 1_555 yes
C(126) C(26) H(26C) 112.85(4) 1_555 1_555 1_555 yes
H(26A) C(26) H(26B) 107.30(4) 1_555 1_555 1_555 yes
H(26A) C(26) H(26C) 109.77(4) 1_555 1_555 1_555 yes
H(26B) C(26) H(26C) 104.76(4) 1_555 1_555 1_555 yes
CL(1) C(111) C(112) 118.38(2) 1_555 1_555 1_555 yes
CL(1) C(111) C(113) 118.34(2) 1_555 1_555 3_667 yes
C(112) C(111) C(113) 123.02(3) 1_555 1_555 3_667 yes
O(2) C(112) C(111) 124.53(3) 1_555 1_555 1_555 yes
O(3) C(113) C(111) 124.95(3) 1_555 1_555 3_667 yes

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
C(124) N(125) C(126) C(121) 0.87(3) 1_555 1_555 1_555 1_555 yes
C(126) N(125) C(124) C(123) 0.57(4) 1_555 1_555 1_555 1_555 yes
C(126) N(125) C(124) C(24) -178.18(5) 1_555 1_555 1_555 1_555 yes
C(124) N(125) C(126) C(26) -178.46(5) 1_555 1_555 1_555 1_555 yes
H(125) N(125) C(124) C(123) 174.75(5) 1_555 1_555 1_555 1_555 yes
H(125) N(125) C(124) C(24) -4.00(3) 1_555 1_555 1_555 1_555 yes
H(125) N(125) C(126) C(121) -173.36(5) 1_555 1_555 1_555 1_555 yes
H(125) N(125) C(126) C(26) 7.31(3) 1_555 1_555 1_555 1_555 yes
C(122) C(121) C(126) N(125) -1.55(4) 1_555 1_555 1_555 1_555 yes
C(126) C(121) C(122) C(123) 0.82(4) 1_555 1_555 1_555 1_555 yes
C(122) C(121) C(126) C(26) 177.73(6) 1_555 1_555 1_555 1_555 yes
C(126) C(121) C(122) H(122) -178.10(6) 1_555 1_555 1_555 1_555 yes
H(121) C(121) C(122) C(123) -178.00(7) 1_555 1_555 1_555 1_555 yes
H(121) C(121) C(122) H(122) 3.08(4) 1_555 1_555 1_555 1_555 yes
H(121) C(121) C(126) N(125) 177.26(6) 1_555 1_555 1_555 1_555 yes
H(121) C(121) C(126) C(26) -3.46(4) 1_555 1_555 1_555 1_555 yes
C(121) C(122) C(123) C(124) 0.62(4) 1_555 1_555 1_555 1_555 yes
C(121) C(122) C(123) H(123) -179.72(7) 1_555 1_555 1_555 1_555 yes
H(122) C(122) C(123) C(124) 179.55(7) 1_555 1_555 1_555 1_555 yes
H(122) C(122) C(123) H(123) -0.79(4) 1_555 1_555 1_555 1_555 yes
C(122) C(123) C(124) N(125) -1.31(4) 1_555 1_555 1_555 1_555 yes
C(122) C(123) C(124) C(24) 177.35(6) 1_555 1_555 1_555 1_555 yes
H(123) C(123) C(124) N(125) 179.03(6) 1_555 1_555 1_555 1_555 yes
H(123) C(123) C(124) C(24) -2.30(4) 1_555 1_555 1_555 1_555 yes
N(125) C(124) C(24) H(24A) -165.33(5) 1_555 1_555 1_555 1_555 yes
N(125) C(124) C(24) H(24B) 72.32(4) 1_555 1_555 1_555 1_555 yes
N(125) C(124) C(24) H(24C) -50.97(4) 1_555 1_555 1_555 1_555 yes
C(123) C(124) C(24) H(24A) 15.98(4) 1_555 1_555 1_555 1_555 yes
C(123) C(124) C(24) H(24B) -106.36(5) 1_555 1_555 1_555 1_555 yes
C(123) C(124) C(24) H(24C) 130.34(6) 1_555 1_555 1_555 1_555 yes
N(125) C(126) C(26) H(26A) -32.16(4) 1_555 1_555 1_555 1_555 yes
N(125) C(126) C(26) H(26B) 86.90(4) 1_555 1_555 1_555 1_555 yes
N(125) C(126) C(26) H(26C) -156.84(5) 1_555 1_555 1_555 1_555 yes
C(121) C(126) C(26) H(26A) 148.55(6) 1_555 1_555 1_555 1_555 yes
C(121) C(126) C(26) H(26B) -92.39(5) 1_555 1_555 1_555 1_555 yes
C(121) C(126) C(26) H(26C) 23.87(4) 1_555 1_555 1_555 1_555 yes
CL(1) C(111) C(112) O(2) 1.56(3) 1_555 1_555 1_555 1_555 yes
C(113) C(111) C(112) O(2) 175.49(5) 3_667 1_555 1_555 1_555 yes
####################################################################### 
# 
# 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_2_(2,6)_neutron
_database_code_depnum_ccdc_archive 'CCDC 1478090'
_audit_update_record             
;
2016-05-04 deposited with the CCDC.
2016-06-13 downloaded from the CCDC.
;

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         
;
C6 Cl2 O4, 2(C7 H10 N)  
;
_chemical_formula_sum            'C20 H20 Cl2 N2 O4'
_chemical_formula_weight         423.28
_chemical_compound_source        commercial

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.1427(3)
_cell_length_b                   9.3025(4)
_cell_length_c                   14.7753(6)
_cell_angle_alpha                90
_cell_angle_beta                 94.526(2)
_cell_angle_gamma                90
_cell_volume                     978.68(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5216
_cell_measurement_theta_min      3.5
_cell_measurement_theta_max      61.9
_cell_measurement_wavelength     0.9484

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          4
_exptl_crystal_size_mid          3
_exptl_crystal_size_min          2
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             238
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.1665
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.9484
_diffrn_radiation_probe          neutron
_diffrn_radiation_type           neutron
_diffrn_radiation_source         'nuclear reactor'

_diffrn_radiation_monochromator  Cu(220)
_diffrn_measurement_device_type  '4-circles Eulerian cradle'
_diffrn_measurement_method       'omega scans'
_diffrn_detector                 'multiwire proportional chamber'
_diffrn_detector_area_resol_mean 0.52
_diffrn_detector_details         
;
ILL cylindrically shaped large-area position sensitive detector 
with 120 by 30 deg detection angle (resolution: 0.4 by 0.64 pixels/mm)
;

_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.065
_diffrn_reflns_av_unetI/netI     0.1021
_diffrn_reflns_number            5216
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.457
_diffrn_reflns_theta_max         61.891
_diffrn_reflns_theta_full        34.683
_diffrn_measured_fraction_theta_full 0.958
_diffrn_measured_fraction_theta_max 0.79
_diffrn_reflns_Laue_measured_fraction_full 0.958
_diffrn_reflns_Laue_measured_fraction_max 0.79
_diffrn_reflns_point_group_measured_fraction_full 0.958
_diffrn_reflns_point_group_measured_fraction_max 0.79
_reflns_Friedel_coverage         0
_reflns_number_total             5216
_reflns_number_gt                3316
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'ILL-MAD software'
_computing_cell_refinement       'Dirax (Duisenberg, 1992)'
_computing_data_reduction        'PFIND, RETREAT (Wilkinson et al.,1988)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_atom_sites_solution_hydrogens   difmap

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
goodness of fit S are based on F², conventional R-factors R are based 
on F, with F set to zero for negative F². The threshold expression of 
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
not relevant to the choice of reflections for refinement.  R-factors based 
on F² are statistically about twice as large as those based on F, and R- 
factors based on ALL data will be even larger. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1649P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0035(18)
_refine_ls_number_reflns         5216
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.1269
_refine_ls_R_factor_gt           0.0888
_refine_ls_wR_factor_ref         0.2545
_refine_ls_wR_factor_gt          0.223
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_restrained_S_all      0.989
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         4.145
_refine_diff_density_min         -2.234
_refine_diff_density_rms         0.402

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_length_neutron
_atom_type_scat_source
C C 0.0000 0.0000 6.646 'Neutron Data Booklet Table 1.1-8'
H H 0.0000 0.0000 -3.739 'Neutron Data Booklet Table 1.1-8'
N N 0.0000 0.0000 9.36 'Neutron Data Booklet Table 1.1-8'
O O 0.0000 0.0000 5.803 'Neutron Data Booklet Table 1.1-8'
Cl Cl 0.0000 0.0000 9.577 'Neutron Data Booklet Table 1.1-8'

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 0.59617(15) 0.36743(9) 1.19646(6) 0.02247(19) Uani 1 1 d . . . . .
O2 O 0.6829(3) 0.24493(16) 1.01831(11) 0.0250(3) Uani 1 1 d . . . . .
O3 O 0.5909(3) 0.35195(16) 0.85297(10) 0.0232(3) Uani 1 1 d . . . . .
N125 N 0.89847(15) 0.13035(9) 0.89979(6) 0.02109(18) Uani 1 1 d . . . . .
C121 C 1.0203(2) -0.08262(15) 0.84122(10) 0.0263(3) Uani 1 1 d . . . . .
C122 C 1.1739(2) -0.00546(17) 0.81535(11) 0.0283(3) Uani 1 1 d . . . . .
C123 C 1.1871(2) 0.14147(17) 0.83261(11) 0.0279(3) Uani 1 1 d . . . . .
C124 C 1.0459(2) 0.20906(14) 0.87680(10) 0.0232(2) Uani 1 1 d . . . . .
C126 C 0.8791(2) -0.01191(13) 0.88340(9) 0.0220(2) Uani 1 1 d . . . . .
C24 C 1.0498(3) 0.36447(16) 0.90203(13) 0.0304(3) Uani 1 1 d . . . . .
C26 C 0.7054(3) -0.08253(16) 0.91105(12) 0.0296(3) Uani 1 1 d . . . . .
C111 C 0.5381(2) 0.43716(12) 1.08881(8) 0.0188(2) Uani 1 1 d . . . . .
C112 C 0.5949(2) 0.36186(12) 1.01390(8) 0.0187(2) Uani 1 1 d . . . . .
C113 C 0.54915(19) 0.42625(12) 0.91815(8) 0.0181(2) Uani 1 1 d . . . . .
H121 H 1.0093(8) -0.1982(4) 0.8298(3) 0.0491(10) Uani 1 1 d . . . . .
H122 H 1.2836(7) -0.0598(5) 0.7804(3) 0.0504(10) Uani 1 1 d . . . . .
H123 H 1.3066(6) 0.2044(5) 0.8140(3) 0.0483(9) Uani 1 1 d . . . . .
H125 H 0.7924(5) 0.1834(3) 0.9359(2) 0.0337(6) Uani 1 1 d . . . . .
H24A H 1.1548(9) 0.4215(5) 0.8672(5) 0.0677(16) Uani 1 1 d . . . . .
H24B H 1.0787(14) 0.3772(6) 0.9736(4) 0.084(2) Uani 1 1 d . . . . .
H24C H 0.9166(7) 0.4145(5) 0.8825(5) 0.0591(13) Uani 1 1 d . . . . .
H26A H 0.6636(11) -0.0413(8) 0.9738(5) 0.084(2) Uani 1 1 d . . . . .
H26B H 0.5945(9) -0.0690(11) 0.8621(6) 0.102(3) Uani 1 1 d . . . . .
H26C H 0.7243(10) -0.1963(5) 0.9197(6) 0.078(2) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   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 C111 1.7374(15) . ?
O2 C112 1.2555(19) . ?
O3 C113 1.2407(17) . ?
N125 C124 1.3478(17) . ?
N125 C126 1.3505(15) . ?
C121 C122 1.390(2) . ?
C121 C126 1.3918(19) . ?
C122 C123 1.392(2) . ?
C123 C124 1.394(2) . ?
C124 C24 1.493(2) . ?
C126 C26 1.490(2) . ?
C111 C112 1.3968(15) . ?
C111 C113 1.4155(17) 3_667 ?
C112 C113 1.5473(17) . ?
C113 C111 1.4155(17) 3_667 ?

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
C124 N125 C126 123.92(11) . . ?
C122 C121 C126 119.64(13) . . ?
C121 C122 C123 120.01(13) . . ?
C122 C123 C124 119.19(14) . . ?
N125 C124 C123 118.78(12) . . ?
N125 C124 C24 117.56(12) . . ?
C123 C124 C24 123.65(14) . . ?
N125 C126 C121 118.42(13) . . ?
N125 C126 C26 117.30(11) . . ?
C121 C126 C26 124.27(13) . . ?
C112 C111 C113 123.11(11) . 3_667 ?
C112 C111 Cl1 118.36(10) . . ?
C113 C111 Cl1 118.27(9) 3_667 . ?
O2 C112 C111 124.67(13) . . ?
O2 C112 C113 116.84(11) . . ?
C111 C112 C113 118.48(10) . . ?
O3 C113 C111 125.10(13) . 3_667 ?
O3 C113 C112 116.60(12) . . ?
C111 C113 C112 118.29(9) 3_667 . ?

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

data_1_(3,4)_shelx
_database_code_depnum_ccdc_archive 'CCDC 1478091'
_audit_update_record             
;
2016-05-04 deposited with the CCDC.
2016-06-13 downloaded from the CCDC.
;

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         
;
C6 H Cl2 O4, C7 H10 N  
;
_chemical_formula_sum            'C13 H11 Cl2 N O4'
_chemical_formula_weight         316.13

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14

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

_cell_length_a                   10.6010(2)
_cell_length_b                   5.16790(10)
_cell_length_c                   24.3363(4)
_cell_angle_alpha                90
_cell_angle_beta                 97.1990(10)
_cell_angle_gamma                90
_cell_volume                     1322.75(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    13865
_cell_measurement_theta_min      1
_cell_measurement_theta_max      50.62
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.16
_exptl_crystal_density_diffrn    1.587
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.503
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5469
_exptl_absorpt_correction_T_max  0.7495
_exptl_absorpt_process_details   'SADABS, Bruker(2001)'

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      0.6777E-3
_diffrn_orient_matrix_UB_21      0.896141E-1
_diffrn_orient_matrix_UB_31      0.317662E-1
_diffrn_orient_matrix_UB_12      0.1628061
_diffrn_orient_matrix_UB_22      0.338455E-1
_diffrn_orient_matrix_UB_32      -0.989533E-1
_diffrn_orient_matrix_UB_13      -0.221693E-1
_diffrn_orient_matrix_UB_23      0.165921E-1
_diffrn_orient_matrix_UB_33      -0.307997E-1
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_number            13865
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -52
_diffrn_reflns_limit_l_max       52
_diffrn_reflns_theta_min         2.4
_diffrn_reflns_theta_max         50.61
_diffrn_reflns_theta_full        50.61
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_reflns_number_total             13865
_reflns_number_gt                10378
_reflns_threshold_expression     >2σ(I)
_diffrn_reflns_reduction_process 
;
 Scaled and merged with Sortav
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0529P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         13865
_refine_ls_number_parameters     225
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0328
_refine_ls_wR_factor_ref         0.0965
_refine_ls_wR_factor_gt          0.0909
_refine_ls_goodness_of_fit_ref   1.02
_refine_ls_restrained_S_all      1.02
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.69
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.073

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl11 Cl 0.187014(11) 0.51564(2) 0.047654(5) 0.01663(2) Uani 1 1 d . . .
Cl12 Cl 0.485285(11) -0.35921(2) 0.194971(5) 0.01730(2) Uani 1 1 d . . .
O6 O 0.38323(4) 0.14176(8) 0.017039(15) 0.01866(6) Uani 1 1 d . . .
O5 O 0.51205(4) -0.21732(8) 0.077913(17) 0.01908(6) Uani 1 1 d . . .
O3 O 0.27404(4) -0.02443(8) 0.222562(15) 0.01828(6) Uani 1 1 d . . .
O2 O 0.16800(4) 0.38476(8) 0.167703(15) 0.01832(6) Uani 1 1 d . . .
N125 N 0.18038(5) 0.41931(10) 0.280022(18) 0.02043(7) Uani 1 1 d . . .
C121 C 0.05035(5) 0.30638(11) 0.34807(2) 0.02020(8) Uani 1 1 d . . .
C122 C 0.11499(4) 0.48424(8) 0.384762(19) 0.01449(6) Uani 1 1 d . . .
C123 C 0.21635(4) 0.62685(8) 0.367665(19) 0.01465(6) Uani 1 1 d . . .
C124 C 0.24598(5) 0.58942(10) 0.31435(2) 0.01823(7) Uani 1 1 d . . .
C126 C 0.08556(6) 0.27643(12) 0.29600(2) 0.02279(9) Uani 1 1 d . . .
C22 C 0.07742(6) 0.52101(13) 0.44153(2) 0.02217(9) Uani 1 1 d . . .
C23 C 0.29130(6) 0.81631(12) 0.40552(3) 0.02345(9) Uani 1 1 d . . .
C111 C 0.26373(4) 0.27292(8) 0.088156(17) 0.01332(5) Uani 1 1 d . . .
C112 C 0.23954(4) 0.24503(8) 0.142907(17) 0.01328(5) Uani 1 1 d . . .
C113 C 0.30619(4) 0.02018(8) 0.177008(17) 0.01306(5) Uani 1 1 d . . .
C114 C 0.40418(4) -0.12541(8) 0.153911(17) 0.01374(6) Uani 1 1 d . . .
C115 C 0.42686(4) -0.08266(9) 0.101217(18) 0.01394(6) Uani 1 1 d . . .
C116 C 0.35483(4) 0.12175(8) 0.064964(17) 0.01339(5) Uani 1 1 d . . .
H121 H -0.0144(10) 0.202(2) 0.3576(5) 0.032(3) Uiso 1 1 d . . .
H124 H 0.3104(10) 0.6777(18) 0.2991(4) 0.027(2) Uiso 1 1 d . . .
H125 H 0.1984(13) 0.404(3) 0.2434(6) 0.053(4) Uiso 1 1 d . . .
H126 H 0.0466(10) 0.167(2) 0.2685(5) 0.032(3) Uiso 1 1 d . . .
H22A H 0.1466(11) 0.4747(19) 0.4685(4) 0.029(3) Uiso 1 1 d . . .
H22B H 0.0494(10) 0.698(2) 0.4466(5) 0.032(3) Uiso 1 1 d . . .
H22C H 0.0051(13) 0.410(2) 0.4481(6) 0.051(3) Uiso 1 1 d . . .
H23A H 0.3603(12) 0.887(2) 0.3895(5) 0.044(3) Uiso 1 1 d . . .
H23B H 0.3330(11) 0.728(2) 0.4380(5) 0.039(3) Uiso 1 1 d . . .
H23C H 0.2332(11) 0.944(2) 0.4160(5) 0.034(3) Uiso 1 1 d . . .
H3 H 0.5136(12) -0.171(2) 0.0437(6) 0.046(3) Uiso 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
Cl11 C111 1.7336(4) . ?
Cl12 C114 1.7269(4) . ?
O6 C116 1.2448(6) . ?
O5 C115 1.3228(6) . ?
O5 H3 0.870(13) . ?
O3 C113 1.2219(6) . ?
O2 C112 1.2552(5) . ?
N125 C126 1.3434(9) . ?
N125 C124 1.3449(7) . ?
N125 H125 0.938(14) . ?
C121 C126 1.3740(9) . ?
C121 C122 1.3995(7) . ?
C121 H121 0.924(10) . ?
C122 C123 1.4082(6) . ?
C122 C22 1.4970(7) . ?
C123 C124 1.3862(7) . ?
C123 C23 1.5018(7) . ?
C124 H124 0.936(10) . ?
C126 H126 0.931(11) . ?
C22 H22A 0.952(11) . ?
C22 H22B 0.974(11) . ?
C22 H22C 0.986(14) . ?
C23 H23A 0.945(12) . ?
C23 H23B 0.970(12) . ?
C23 H23C 0.957(11) . ?
C111 C112 1.3956(6) . ?
C111 C116 1.4136(6) . ?
C112 C113 1.5464(6) . ?
C113 C114 1.4517(6) . ?
C114 C115 1.3522(6) . ?
C115 C116 1.5194(6) . ?

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
C115 O5 H3 111.2(8) . . ?
C126 N125 C124 121.80(5) . . ?
C126 N125 H125 118.6(8) . . ?
C124 N125 H125 119.6(8) . . ?
C126 C121 C122 119.64(5) . . ?
C126 C121 H121 117.4(7) . . ?
C122 C121 H121 122.9(7) . . ?
C121 C122 C123 119.08(5) . . ?
C121 C122 C22 120.44(4) . . ?
C123 C122 C22 120.49(4) . . ?
C124 C123 C122 118.32(4) . . ?
C124 C123 C23 120.04(5) . . ?
C122 C123 C23 121.64(5) . . ?
N125 C124 C123 120.83(5) . . ?
N125 C124 H124 114.7(6) . . ?
C123 C124 H124 124.4(6) . . ?
N125 C126 C121 120.31(5) . . ?
N125 C126 H126 113.9(7) . . ?
C121 C126 H126 125.7(7) . . ?
C122 C22 H22A 109.5(7) . . ?
C122 C22 H22B 110.9(7) . . ?
H22A C22 H22B 111.7(9) . . ?
C122 C22 H22C 112.3(8) . . ?
H22A C22 H22C 106.8(10) . . ?
H22B C22 H22C 105.6(10) . . ?
C123 C23 H23A 112.0(8) . . ?
C123 C23 H23B 110.1(7) . . ?
H23A C23 H23B 102.8(10) . . ?
C123 C23 H23C 107.6(7) . . ?
H23A C23 H23C 113.7(10) . . ?
H23B C23 H23C 110.5(10) . . ?
C112 C111 C116 122.72(4) . . ?
C112 C111 Cl11 119.23(3) . . ?
C116 C111 Cl11 117.91(3) . . ?
O2 C112 C111 126.44(4) . . ?
O2 C112 C113 115.93(4) . . ?
C111 C112 C113 117.63(4) . . ?
O3 C113 C114 123.23(4) . . ?
O3 C113 C112 117.91(4) . . ?
C114 C113 C112 118.86(4) . . ?
C115 C114 C113 120.23(4) . . ?
C115 C114 Cl12 121.89(3) . . ?
C113 C114 Cl12 117.85(3) . . ?
O5 C115 C114 122.19(4) . . ?
O5 C115 C116 115.93(4) . . ?
C114 C115 C116 121.88(4) . . ?
O6 C116 C111 125.85(4) . . ?
O6 C116 C115 116.03(4) . . ?
C111 C116 C115 118.11(4) . . ?

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
C126 C121 C122 C123 -0.85(8) . . . . ?
C126 C121 C122 C22 179.56(5) . . . . ?
C121 C122 C123 C124 1.58(7) . . . . ?
C22 C122 C123 C124 -178.82(5) . . . . ?
C121 C122 C123 C23 -178.63(5) . . . . ?
C22 C122 C123 C23 0.96(8) . . . . ?
C126 N125 C124 C123 -1.10(8) . . . . ?
C122 C123 C124 N125 -0.65(7) . . . . ?
C23 C123 C124 N125 179.56(5) . . . . ?
C124 N125 C126 C121 1.88(9) . . . . ?
C122 C121 C126 N125 -0.88(9) . . . . ?
C116 C111 C112 O2 173.93(5) . . . . ?
Cl11 C111 C112 O2 -1.87(7) . . . . ?
C116 C111 C112 C113 -6.32(6) . . . . ?
Cl11 C111 C112 C113 177.88(3) . . . . ?
O2 C112 C113 O3 8.34(6) . . . . ?
C111 C112 C113 O3 -171.44(4) . . . . ?
O2 C112 C113 C114 -171.05(4) . . . . ?
C111 C112 C113 C114 9.18(6) . . . . ?
O3 C113 C114 C115 173.69(5) . . . . ?
C112 C113 C114 C115 -6.97(6) . . . . ?
O3 C113 C114 Cl12 -4.12(6) . . . . ?
C112 C113 C114 Cl12 175.23(3) . . . . ?
C113 C114 C115 O5 -177.54(4) . . . . ?
Cl12 C114 C115 O5 0.18(7) . . . . ?
C113 C114 C115 C116 1.84(7) . . . . ?
Cl12 C114 C115 C116 179.56(3) . . . . ?
C112 C111 C116 O6 -177.97(5) . . . . ?
Cl11 C111 C116 O6 -2.11(7) . . . . ?
C112 C111 C116 C115 1.28(7) . . . . ?
Cl11 C111 C116 C115 177.13(3) . . . . ?
O5 C115 C116 O6 0.02(6) . . . . ?
C114 C115 C116 O6 -179.40(4) . . . . ?
O5 C115 C116 C111 -179.30(4) . . . . ?
C114 C115 C116 C111 1.29(7) . . . . ?

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

data_1_(3,4)_xd
_database_code_depnum_ccdc_archive 'CCDC 1478092'
_audit_update_record             
;
2016-05-04 deposited with the CCDC.
2016-06-13 downloaded from the CCDC.
;

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         
;
C6 H Cl2 O4, C7 H10 N  
;
_chemical_formula_sum            'C13 H11 Cl2 N O4'
_chemical_formula_weight         316.13

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14

loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,1/2-Y,1/2+Z

_cell_length_a                   10.6010(2)
_cell_length_b                   5.16790(10)
_cell_length_c                   24.3363(4)
_cell_angle_alpha                90
_cell_angle_beta                 97.1990(10)
_cell_angle_gamma                90
_cell_volume                     1322.75(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    13865
_cell_measurement_theta_min      1
_cell_measurement_theta_max      50.62
_cell_measurement_wavelength     0.71073


#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.16
_exptl_crystal_density_diffrn    1.587
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.503
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5469
_exptl_absorpt_correction_T_max  0.7495
_exptl_absorpt_process_details   'SADABS, Bruker(2001)'

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      0.6777E-3
_diffrn_orient_matrix_UB_21      0.896141E-1
_diffrn_orient_matrix_UB_31      0.317662E-1
_diffrn_orient_matrix_UB_12      0.1628061
_diffrn_orient_matrix_UB_22      0.338455E-1
_diffrn_orient_matrix_UB_32      -0.989533E-1
_diffrn_orient_matrix_UB_13      -0.221693E-1
_diffrn_orient_matrix_UB_23      0.165921E-1
_diffrn_orient_matrix_UB_33      -0.307997E-1
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_number            13865
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -52
_diffrn_reflns_limit_l_max       52
_diffrn_reflns_theta_min         2.4
_diffrn_reflns_theta_max         50.61
_diffrn_reflns_theta_full        50.61
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_reflns_number_total             13865
_reflns_number_gt                10378
_reflns_threshold_expression     >2σ(I)
_diffrn_reflns_reduction_process 
;
 Scaled and merged with Sortav
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom


#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
        ?
;
_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
        calc w1 = 1/[s²(Fo)]
;
_refine_ls_extinction_method     none
_refine_ls_number_reflns         10950
_refine_ls_number_parameters     542
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.051
_refine_ls_R_factor_gt           0.027
_refine_ls_wR_factor_ref         0.024
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_shift/su_max          0.00001
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.060

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, 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_symmetry_multiplicity
Cl(1) Cl 0.187012(9) 0.515639(17) 0.047663(4) 0.016 Uani 1 4
Cl(2) Cl 0.485282(9) -0.359195(18) 0.194969(4) 0.017 Uani 1 4
O(2) O 0.16809(5) 0.38489(10) 0.167650(18) 0.018 Uani 1 4
O(3) O 0.27420(5) -0.02431(10) 0.222583(17) 0.018 Uani 1 4
O(5) O 0.51197(5) -0.21711(10) 0.077900(19) 0.019 Uani 1 4
O(6) O 0.38298(5) 0.14148(10) 0.017026(17) 0.019 Uani 1 4
N(125) N 0.18048(5) 0.41942(11) 0.280006(19) 0.02 Uani 1 4
C(121) C 0.05020(5) 0.30636(10) 0.34823(2) 0.02 Uani 1 4
C(122) C 0.11503(4) 0.48435(8) 0.384812(17) 0.014 Uani 1 4
C(123) C 0.21641(4) 0.62692(8) 0.367707(17) 0.014 Uani 1 4
C(124) C 0.24592(5) 0.58923(9) 0.31434(2) 0.018 Uani 1 4
C(126) C 0.08574(5) 0.27615(11) 0.29586(2) 0.023 Uani 1 4
C(22) C 0.07736(5) 0.52107(11) 0.44148(2) 0.022 Uani 1 4
C(23) C 0.29132(5) 0.81609(10) 0.40549(2) 0.023 Uani 1 4
C(111) C 0.26377(4) 0.27310(7) 0.088082(16) 0.013 Uani 1 4
C(112) C 0.23956(4) 0.24479(7) 0.142936(16) 0.013 Uani 1 4
C(113) C 0.30627(4) 0.02039(7) 0.176963(15) 0.013 Uani 1 4
C(114) C 0.40409(4) -0.12573(7) 0.153933(16) 0.014 Uani 1 4
C(115) C 0.42693(4) -0.08269(8) 0.101085(16) 0.014 Uani 1 4
C(116) C 0.35489(4) 0.12165(7) 0.064976(16) 0.013 Uani 1 4
H(121) H -0.025662 0.183865 0.359225 0.034 Uani 1 4
H(124) H 0.320482 0.691519 0.296724 0.031 Uani 1 4
H(125) H 0.200234 0.402759 0.239656 0.029 Uani 1 4
H(126) H 0.040147 0.149251 0.26394 0.031 Uani 1 4
H(22A) H 0.15431 0.469579 0.471524 0.039 Uani 1 4
H(22B) H 0.04694 0.713454 0.44702 0.042 Uani 1 4
H(22C) H -0.000308 0.40215 0.448611 0.041 Uani 1 4
H(23A) H 0.368643 0.89549 0.387509 0.038 Uani 1 4
H(23B) H 0.336767 0.719604 0.440951 0.038 Uani 1 4
H(23C) H 0.227098 0.957051 0.417053 0.04 Uani 1 4
H(5) H 0.513792 -0.165094 0.03954 0.028 Uani 1 4

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl(1) 0.01967(3) 0.01627(3) 0.01343(3) 0.00276(2) 0.00189(2) 0.00591(2)
Cl(2) 0.02007(3) 0.01760(3) 0.01348(3) 0.00299(3) 0.00113(2) 0.00615(3)
O(2) 0.02136(16) 0.02171(16) 0.01241(11) -0.00021(12) 0.00455(11) 0.00941(13)
O(3) 0.02363(16) 0.02057(15) 0.01140(11) 0.00318(11) 0.00641(11) 0.00544(13)
O(5) 0.02107(16) 0.02235(16) 0.01461(12) 0.00351(12) 0.00682(11) 0.01092(13)
O(6) 0.02116(16) 0.02429(17) 0.01158(11) 0.00353(12) 0.00632(11) 0.00814(14)
N(125) 0.02452(18) 0.02544(18) 0.01118(11) -0.00204(13) 0.00394(12) 0.00575(15)
C(121) 0.01947(16) 0.02188(16) 0.01903(15) -0.00445(14) 0.00307(13)
-0.00687(13)
C(122) 0.01506(12) 0.01645(12) 0.01222(11) -0.00090(10) 0.00393(9) -0.00318(10)
C(123) 0.01672(13) 0.01464(12) 0.01265(11) 0.00004(10) 0.00404(10) -0.00287(10)
C(124) 0.02081(16) 0.02112(15) 0.01366(12) 0.00248(12) 0.00675(11) 0.00022(13)
C(126) 0.02527(19) 0.02478(18) 0.01743(16) -0.00842(15) 0.00027(15)
-0.00115(15)
C(22) 0.02275(17) 0.0303(2) 0.01483(14) -0.00215(15) 0.00791(12) -0.00512(15)
C(23) 0.02662(19) 0.02115(16) 0.02240(18) -0.00370(15) 0.00356(15) -0.01015(15)
C(111) 0.01509(12) 0.01430(11) 0.01033(10) 0.00096(9) 0.00222(9) 0.00402(9)
C(112) 0.01473(12) 0.01509(11) 0.00993(10) -0.00010(9) 0.00260(9) 0.00360(9)
C(113) 0.01510(11) 0.01455(11) 0.00958(9) 0.00061(9) 0.00241(8) 0.00210(9)
C(114) 0.01501(12) 0.01509(12) 0.01068(10) 0.00138(10) 0.00215(9) 0.00390(9)
C(115) 0.01486(12) 0.01582(12) 0.01104(10) 0.00115(10) 0.00307(9) 0.00458(10)
C(116) 0.01468(12) 0.01558(12) 0.00990(9) 0.00083(9) 0.00304(9) 0.00378(10)
H(121) 0.031664 0.042598 0.027959 -0.007047 0.010115 -0.014186
H(124) 0.033802 0.032549 0.027017 0.000811 0.010872 -0.007562
H(125) 0.033908 0.035104 0.019504 -0.002666 0.008196 -0.002761
H(126) 0.032815 0.037584 0.022658 -0.009045 0.003872 -0.006846
H(22A) 0.034444 0.055875 0.026218 -0.00275 0.0018 -0.00282
H(22B) 0.056476 0.034447 0.037184 -0.007546 0.01633 0.00202
H(22C) 0.039066 0.052172 0.034979 -0.012066 0.014309 -0.024082
H(23A) 0.042179 0.043021 0.03232 -0.002889 0.016686 -0.016875
H(23B) 0.050279 0.03323 0.027475 0.005558 -0.003167 -0.007981
H(23C) 0.040216 0.036719 0.044667 -0.013247 0.009547 0.002931
H(5) 0.03091 0.033807 0.020163 0.004407 0.006511 0.009123


#----------------------------------------------------------------------------#
#                   MULTIPOLE PARAMETERS                                     #
#----------------------------------------------------------------------------#

loop_
_atom_rho_multipole_atom_label
_atom_rho_multipole_coeff_Pv
_atom_rho_multipole_coeff_P00
_atom_rho_multipole_coeff_P11
_atom_rho_multipole_coeff_P1-1
_atom_rho_multipole_coeff_P10
_atom_rho_multipole_coeff_P20
_atom_rho_multipole_coeff_P21
_atom_rho_multipole_coeff_P2-1
_atom_rho_multipole_coeff_P22
_atom_rho_multipole_coeff_P2-2
_atom_rho_multipole_coeff_P30
_atom_rho_multipole_coeff_P31
_atom_rho_multipole_coeff_P3-1
_atom_rho_multipole_coeff_P32
_atom_rho_multipole_coeff_P3-2
_atom_rho_multipole_coeff_P33
_atom_rho_multipole_coeff_P3-3
_atom_rho_multipole_coeff_P40
_atom_rho_multipole_coeff_P41
_atom_rho_multipole_coeff_P4-1
_atom_rho_multipole_coeff_P42
_atom_rho_multipole_coeff_P4-2
_atom_rho_multipole_coeff_P43
_atom_rho_multipole_coeff_P4-3
_atom_rho_multipole_coeff_P44
_atom_rho_multipole_coeff_P4-4
_atom_rho_multipole_kappa
_atom_rho_multipole_kappa_prime0
_atom_rho_multipole_kappa_prime1
_atom_rho_multipole_kappa_prime2
_atom_rho_multipole_kappa_prime3
_atom_rho_multipole_kappa_prime4
Cl(1) 7.30(3) 0 0.024(11) 0.037(11) -0.029(10) -0.129(13) 0.016(13) 0.032(12)
0.035(13) 0.009(13) 0.086(10) -0.022(9) 0.001(10) 0.031(10) 0.002(10) 0.014(10)
0.000(10) 0.021(14) 0.012(12) -0.001(13) -0.034(13) 0.009(13) 0.031(13)
0.015(14) -0.016(13) -0.017(13) 1.002516 1 1 1 1 1
Cl(2) 7.22(3) 0 0.023(11) 0.011(11) -0.018(11) -0.135(13) 0.009(13) -0.058(13)
0.015(13) 0.005(13) 0.096(10) -0.020(9) -0.010(10) -0.001(10) 0.003(10)
0.032(10) 0.017(10) 0.031(14) 0.004(12) 0.001(13) -0.027(14) -0.012(13)
0.026(13) -0.015(13) -0.013(13) 0.005(13) 1.002516 1 1 1 1 1
O(2) 6.090(17) 0 -0.024(11) -0.020(9) -0.078(11) -0.021(12) -0.004(11)
0.030(11) -0.055(10) -0.040(10) 0.024(11) 0.023(10) -0.004(10) 0.035(10)
0.017(10) -0.012(9) -0.016(9) 0 0 0 0 0 0 0 0 0 0.995668 0.977221 0.977221
0.977221 0.977221 0.977221
O(3) 6.116(18) 0 -0.033(12) -0.028(10) -0.071(12) -0.004(13) 0.021(12)
-0.014(11) -0.135(10) 0.004(11) 0.017(11) 0.009(11) -0.018(11) 0.018(9)
0.007(10) -0.008(9) -0.005(9) 0 0 0 0 0 0 0 0 0 0.995668 0.977221 0.977221
0.977221 0.977221 0.977221
O(5) 6.06(2) 0 -0.015(12) -0.072(10) -0.053(13) -0.022(13) -0.010(11) 0.048(10)
-0.010(11) -0.008(11) 0.079(12) -0.019(11) -0.014(11) 0.044(10) 0.006(10)
0.008(10) -0.019(9) 0 0 0 0 0 0 0 0 0 0.997832 0.965707 0.965707 0.965707
0.965707 0.965707
O(6) 6.115(18) 0 -0.037(12) -0.007(10) -0.076(11) -0.024(13) 0.005(12)
-0.008(11) -0.112(10) -0.002(11) 0.012(12) -0.002(11) -0.008(11) 0.010(10)
-0.016(9) -0.009(9) 0.001(9) 0 0 0 0 0 0 0 0 0 0.995668 0.977221 0.977221
0.977221 0.977221 0.977221
N(125) 4.96(3) 0 -0.050(14) -0.006(16) -0.003(11) -0.112(12) -0.009(12)
0.004(12) 0.007(14) 0.000(15) -0.020(12) 0.014(11) 0.017(11) -0.001(12)
-0.014(12) 0.172(14) 0.026(16) 0 0 0 0 0 0 0 0 0 0.997327 0.992675 0.992675
0.992675 0.992675 0.992675
C(121) 4.13(3) 0 -0.035(16) 0.011(18) -0.019(14) -0.189(15) 0.012(13)
-0.007(14) -0.036(15) 0.042(16) -0.014(15) 0.033(15) 0.022(15) 0.003(15)
-0.007(15) 0.255(16) -0.040(18) 0 0 0 0 0 0 0 0 0 0.9963 0.973604 0.973604
0.973604 0.973604 0.973604
C(122) 4.10(3) 0 0.052(14) 0.044(15) -0.001(12) -0.251(12) -0.016(12)
-0.015(12) 0.023(14) -0.012(14) -0.007(14) 0.027(13) 0.020(13) -0.004(14)
0.010(14) 0.289(16) 0.013(18) 0 0 0 0 0 0 0 0 0 0.9963 0.973604 0.973604
0.973604 0.973604 0.973604
C(123) 4.04(3) 0 0.021(16) 0.026(14) 0.012(13) -0.186(13) -0.016(13) -0.001(11)
0.013(15) 0.024(14) 0.013(14) -0.020(14) 0.024(12) -0.011(15) 0.015(14)
0.280(16) 0.002(18) 0 0 0 0 0 0 0 0 0 0.9963 0.973604 0.973604 0.973604
0.973604 0.973604
C(124) 4.09(3) 0 -0.050(17) -0.044(15) -0.032(13) -0.203(14) 0.003(13)
0.014(12) 0.005(16) 0.018(15) 0.013(15) 0.053(14) 0.011(13) 0.012(15) 0.009(15)
0.259(17) -0.007(18) 0 0 0 0 0 0 0 0 0 0.9963 0.973604 0.973604 0.973604
0.973604 0.973604
C(126) 4.10(4) 0 0.044(18) -0.041(16) 0.009(14) -0.219(15) -0.002(15) 0.015(12)
0.043(17) 0.019(16) -0.001(16) 0.045(16) -0.017(14) 0.017(16) 0.000(15)
0.274(18) -0.03(2) 0 0 0 0 0 0 0 0 0 0.9963 0.973604 0.973604 0.973604 0.973604
0.973604
C(22) 4.20(6) 0 -0.057(17) 0.018(15) 0.006(15) 0.033(14) 0.021(14) 0.020(14)
-0.030(14) 0.035(15) 0.215(18) -0.014(16) 0.030(15) -0.014(15) 0.044(16)
-0.020(15) -0.181(16) 0 0 0 0 0 0 0 0 0 0.990114 0.931185 0.931185 0.931185
0.931185 0.931185
C(23) 4.25(6) 0 -0.075(15) -0.021(15) 0.066(14) -0.009(14) -0.022(13)
-0.021(14) 0.003(13) 0.023(14) 0.195(18) -0.031(16) 0.021(17) 0.023(15)
0.072(15) -0.007(15) -0.169(16) 0 0 0 0 0 0 0 0 0 0.990114 0.931185 0.931185
0.931185 0.931185 0.931185
C(111) 4.14(3) 0 0.063(15) 0.047(12) -0.020(12) -0.054(12) 0.013(12) -0.013(11)
0.031(14) -0.037(13) -0.003(14) 0.029(13) 0.030(12) -0.002(14) 0.032(13)
0.254(15) 0.027(17) 0 0 0 0 0 0 0 0 0 0.997822 0.972233 0.972233 0.972233
0.972233 0.972233
C(112) 4.04(3) 0 -0.044(13) -0.055(15) -0.016(11) -0.227(13) 0.015(11)
-0.002(12) -0.088(13) 0.040(14) 0.015(14) 0.001(12) 0.053(13) 0.002(14)
-0.002(14) 0.278(16) 0.035(18) 0 0 0 0 0 0 0 0 0 0.997822 0.972233 0.972233
0.972233 0.972233 0.972233
C(113) 4.11(3) 0 -0.031(13) -0.068(15) 0.019(12) -0.259(12) -0.013(11)
-0.006(12) -0.038(13) 0.070(14) -0.013(14) -0.021(12) 0.005(13) 0.009(14)
-0.005(14) 0.333(16) 0.004(18) 0 0 0 0 0 0 0 0 0 0.997822 0.972233 0.972233
0.972233 0.972233 0.972233
C(114) 4.05(3) 0 0.001(15) 0.039(13) 0.005(12) -0.077(12) -0.005(13) 0.003(11)
-0.002(14) -0.059(13) 0.008(14) 0.045(13) 0.002(12) 0.004(14) -0.005(13)
0.238(16) 0.001(17) 0 0 0 0 0 0 0 0 0 0.997822 0.972233 0.972233 0.972233
0.972233 0.972233
C(115) 4.02(3) 0 0.003(13) 0.071(15) 0.002(12) -0.227(13) 0.002(11) 0.013(13)
-0.037(13) -0.066(14) -0.002(14) 0.010(13) 0.038(14) 0.002(14) -0.025(14)
0.322(16) 0.063(18) 0 0 0 0 0 0 0 0 0 0.997822 0.972233 0.972233 0.972233
0.972233 0.972233
C(116) 4.02(3) 0 -0.054(13) -0.041(15) -0.009(12) -0.250(13) 0.003(11)
-0.005(12) -0.110(13) 0.007(14) -0.001(14) -0.022(12) 0.019(13) -0.001(14)
0.011(14) 0.296(16) 0.058(18) 0 0 0 0 0 0 0 0 0 0.997822 0.972233 0.972233
0.972233 0.972233 0.972233
H(121) 0.790(13) 0 0.005(8) -0.030(8) 0.115(10) 0.018(12) 0 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0 1.179001 1.179001 1.179001 1.179001 1.179001 1.179001
H(124) 0.790(13) 0 0.005(8) -0.030(8) 0.115(10) 0.018(12) 0 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0 1.179001 1.179001 1.179001 1.179001 1.179001 1.179001
H(125) 0.69(2) 0 -0.045(12) 0.025(13) 0.098(19) 0.10(2) 0 0 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 1.179001 1.179001 1.179001 1.179001 1.179001 1.179001
H(126) 0.790(13) 0 0.005(8) -0.030(8) 0.115(10) 0.018(12) 0 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0 1.179001 1.179001 1.179001 1.179001 1.179001 1.179001
H(22A) 0.836(15) 0 -0.018(9) -0.023(8) 0.105(11) 0.030(13) 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0 0 1.176633 1.176633 1.176633 1.176633 1.176633 1.176633
H(22B) 0.836(15) 0 -0.018(9) -0.023(8) 0.105(11) 0.030(13) 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0 0 1.176633 1.176633 1.176633 1.176633 1.176633 1.176633
H(22C) 0.836(15) 0 -0.018(9) -0.023(8) 0.105(11) 0.030(13) 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0 0 1.176633 1.176633 1.176633 1.176633 1.176633 1.176633
H(23A) 0.850(15) 0 0.022(9) -0.037(9) 0.095(10) 0.023(12) 0 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0 1.176633 1.176633 1.176633 1.176633 1.176633 1.176633
H(23B) 0.850(15) 0 0.022(9) -0.037(9) 0.095(10) 0.023(12) 0 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0 1.176633 1.176633 1.176633 1.176633 1.176633 1.176633
H(23C) 0.850(15) 0 0.022(9) -0.037(9) 0.095(10) 0.023(12) 0 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0 1.176633 1.176633 1.176633 1.176633 1.176633 1.176633
H(5) 0.724(19) 0 0.046(12) 0.045(11) 0.200(17) 0.13(2) 0 0 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 1.200782 1.200782 1.200782 1.200782 1.200782 1.200782

loop_
_atom_local_axes_atom_label
_atom_local_axes_atom0
_atom_local_axes_ax1
_atom_local_axes_atom1
_atom_local_axes_atom2
_atom_local_axes_ax2
CL(1) C(111) Z CL(1) C(116) Y
CL(2) C(114) Z CL(2) C(115) Y
O(2) C(112) Z O(2) H(125) Y
O(3) C(113) Z O(3) C(114) Y
O(5) H(5) Z O(5) C(115) Y
O(6) C(116) Z O(6) H(5) Y
N(125) C(124) X N(125) C(126) Y
C(121) C(122) X C(121) C(126) Y
C(122) C(121) X C(122) C(123) Y
C(123) C(124) X C(123) C(122) Y
C(124) C(123) X C(124) N(125) Y
C(126) C(121) X C(126) N(125) Y
C(22) H(22A) Z C(22) H(22B) Y
C(23) H(23C) Z C(23) H(23B) Y
C(111) C(112) X C(111) C(116) Y
C(112) C(113) X C(112) C(111) Y
C(113) C(112) X C(113) C(114) Y
C(114) C(115) X C(114) C(113) Y
C(115) C(116) X C(115) C(114) Y
C(116) C(115) X C(116) C(111) Y
H(121) C(121) Z H(121) C(126) Y
H(124) C(124) Z H(124) N(125) Y
H(125) N(125) Z H(125) O(2) Y
H(126) C(126) Z H(126) N(125) Y
H(22A) C(22) Z H(22A) H(22B) Y
H(22B) C(22) Z H(22B) H(22C) Y
H(22C) C(22) Z H(22C) H(22B) Y
H(23A) C(23) Z H(23A) H(23B) Y
H(23B) C(23) Z H(23B) H(23A) Y
H(23C) C(23) Z H(23C) H(23B) Y
H(5) O(5) Z H(5) C(115) Y


#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
CL(1) C(111) 1.7321(3) 1_555 1_555 yes
CL(2) C(114) 1.7258(4) 1_555 1_555 yes
O(2) C(112) 1.2547(6) 1_555 1_555 yes
O(3) C(113) 1.2231(6) 1_555 1_555 yes
O(5) C(115) 1.3195(6) 1_555 1_555 yes
O(5) H(5) 0.9740(5) 1_555 1_555 yes
O(6) C(116) 1.2442(6) 1_555 1_555 yes
N(125) C(124) 1.3432(7) 1_555 1_555 yes
N(125) C(126) 1.3426(9) 1_555 1_555 yes
N(125) H(125) 1.0330(5) 1_555 1_555 yes
C(121) C(122) 1.3992(6) 1_555 1_555 yes
C(121) C(126) 1.3826(8) 1_555 1_555 yes
C(121) H(121) 1.0830(5) 1_555 1_555 yes
C(122) C(123) 1.4082(6) 1_555 1_555 yes
C(122) C(22) 1.4951(6) 1_555 1_555 yes
C(123) C(124) 1.3873(6) 1_555 1_555 yes
C(123) C(23) 1.4996(6) 1_555 1_555 yes
C(124) H(124) 1.0830(5) 1_555 1_555 yes
C(126) H(126) 1.0830(5) 1_555 1_555 yes
C(22) H(22A) 1.0590(5) 1_555 1_555 yes
C(22) H(22B) 1.0590(6) 1_555 1_555 yes
C(22) H(22C) 1.0590(5) 1_555 1_555 yes
C(23) H(23A) 1.0590(6) 1_555 1_555 yes
C(23) H(23B) 1.0590(6) 1_555 1_555 yes
C(23) H(23C) 1.0590(6) 1_555 1_555 yes
C(111) C(112) 1.3983(5) 1_555 1_555 yes
C(111) C(116) 1.4135(5) 1_555 1_555 yes
C(113) C(114) 1.4510(5) 1_555 1_555 yes
C(114) C(115) 1.3565(5) 1_555 1_555 yes
C(115) C(116) 1.5173(5) 1_555 1_555 yes

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C(115) O(5) H(5) 111.18(4) 1_555 1_555 1_555 yes
C(124) N(125) C(126) 121.88(5) 1_555 1_555 1_555 yes
C(124) N(125) H(125) 119.69(6) 1_555 1_555 1_555 yes
C(126) N(125) H(125) 118.37(5) 1_555 1_555 1_555 yes
C(122) C(121) C(126) 119.47(5) 1_555 1_555 1_555 yes
C(122) C(121) H(121) 123.22(5) 1_555 1_555 1_555 yes
C(126) C(121) H(121) 117.28(4) 1_555 1_555 1_555 yes
C(121) C(122) C(123) 119.22(4) 1_555 1_555 1_555 yes
C(121) C(122) C(22) 120.24(4) 1_555 1_555 1_555 yes
C(123) C(122) C(22) 120.55(4) 1_555 1_555 1_555 yes
C(122) C(123) C(124) 118.25(4) 1_555 1_555 1_555 yes
C(122) C(123) C(23) 121.67(4) 1_555 1_555 1_555 yes
C(124) C(123) C(23) 120.08(4) 1_555 1_555 1_555 yes
N(125) C(124) C(123) 120.97(5) 1_555 1_555 1_555 yes
N(125) C(124) H(124) 114.73(5) 1_555 1_555 1_555 yes
C(123) C(124) H(124) 124.30(4) 1_555 1_555 1_555 yes
N(125) C(126) C(121) 120.18(4) 1_555 1_555 1_555 yes
N(125) C(126) H(126) 114.24(6) 1_555 1_555 1_555 yes
C(121) C(126) H(126) 125.51(6) 1_555 1_555 1_555 yes
C(122) C(22) H(22A) 109.46(4) 1_555 1_555 1_555 yes
C(122) C(22) H(22B) 110.94(4) 1_555 1_555 1_555 yes
C(122) C(22) H(22C) 112.37(4) 1_555 1_555 1_555 yes
H(22A) C(22) H(22B) 111.62(5) 1_555 1_555 1_555 yes
H(22A) C(22) H(22C) 106.77(5) 1_555 1_555 1_555 yes
H(22B) C(22) H(22C) 105.58(5) 1_555 1_555 1_555 yes
C(123) C(23) H(23A) 112.16(5) 1_555 1_555 1_555 yes
C(123) C(23) H(23B) 110.16(4) 1_555 1_555 1_555 yes
C(123) C(23) H(23C) 107.62(4) 1_555 1_555 1_555 yes
H(23A) C(23) H(23B) 102.86(5) 1_555 1_555 1_555 yes
H(23A) C(23) H(23C) 113.58(5) 1_555 1_555 1_555 yes
H(23B) C(23) H(23C) 110.44(5) 1_555 1_555 1_555 yes
CL(1) C(111) C(112) 119.24(3) 1_555 1_555 1_555 yes
CL(1) C(111) C(116) 118.07(3) 1_555 1_555 1_555 yes
C(112) C(111) C(116) 122.56(3) 1_555 1_555 1_555 yes
O(2) C(112) C(111) 126.26(4) 1_555 1_555 1_555 yes
O(3) C(113) C(114) 123.07(4) 1_555 1_555 1_555 yes
CL(2) C(114) C(113) 117.97(3) 1_555 1_555 1_555 yes
CL(2) C(114) C(115) 121.87(3) 1_555 1_555 1_555 yes
C(113) C(114) C(115) 120.13(3) 1_555 1_555 1_555 yes
O(5) C(115) C(114) 122.12(4) 1_555 1_555 1_555 yes
O(5) C(115) C(116) 116.10(4) 1_555 1_555 1_555 yes
C(114) C(115) C(116) 121.77(3) 1_555 1_555 1_555 yes
O(6) C(116) C(111) 125.69(4) 1_555 1_555 1_555 yes
O(6) C(116) C(115) 115.99(4) 1_555 1_555 1_555 yes
C(111) C(116) C(115) 118.32(3) 1_555 1_555 1_555 yes

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
H(5) O(5) C(115) C(114) 177.96(7) 1_555 1_555 1_555 1_555 yes
H(5) O(5) C(115) C(116) -1.44(4) 1_555 1_555 1_555 1_555 yes
C(124) N(125) C(126) C(121) 2.01(5) 1_555 1_555 1_555 1_555 yes
C(126) N(125) C(124) C(123) -1.17(5) 1_555 1_555 1_555 1_555 yes
C(126) N(125) C(124) H(124) 179.48(8) 1_555 1_555 1_555 1_555 yes
C(124) N(125) C(126) H(126) 179.16(8) 1_555 1_555 1_555 1_555 yes
H(125) N(125) C(124) C(123) 176.13(8) 1_555 1_555 1_555 1_555 yes
H(125) N(125) C(124) H(124) -3.22(5) 1_555 1_555 1_555 1_555 yes
H(125) N(125) C(126) C(121) -175.32(8) 1_555 1_555 1_555 1_555 yes
H(125) N(125) C(126) H(126) 1.83(5) 1_555 1_555 1_555 1_555 yes
C(122) C(121) C(126) N(125) -0.99(5) 1_555 1_555 1_555 1_555 yes
C(126) C(121) C(122) C(123) -0.80(5) 1_555 1_555 1_555 1_555 yes
C(126) C(121) C(122) C(22) 179.56(7) 1_555 1_555 1_555 1_555 yes
C(122) C(121) C(126) H(126) -177.80(9) 1_555 1_555 1_555 1_555 yes
H(121) C(121) C(122) C(123) 177.07(7) 1_555 1_555 1_555 1_555 yes
H(121) C(121) C(122) C(22) -2.57(4) 1_555 1_555 1_555 1_555 yes
H(121) C(121) C(126) N(125) -178.99(8) 1_555 1_555 1_555 1_555 yes
H(121) C(121) C(126) H(126) 4.21(5) 1_555 1_555 1_555 1_555 yes
C(121) C(122) C(123) C(124) 1.60(4) 1_555 1_555 1_555 1_555 yes
C(121) C(122) C(123) C(23) -178.62(6) 1_555 1_555 1_555 1_555 yes
C(121) C(122) C(22) H(22A) 117.87(6) 1_555 1_555 1_555 1_555 yes
C(121) C(122) C(22) H(22B) -118.51(6) 1_555 1_555 1_555 1_555 yes
C(121) C(122) C(22) H(22C) -0.57(4) 1_555 1_555 1_555 1_555 yes
C(22) C(122) C(123) C(124) -178.76(6) 1_555 1_555 1_555 1_555 yes
C(22) C(122) C(123) C(23) 1.02(4) 1_555 1_555 1_555 1_555 yes
C(123) C(122) C(22) H(22A) -61.76(5) 1_555 1_555 1_555 1_555 yes
C(123) C(122) C(22) H(22B) 61.86(5) 1_555 1_555 1_555 1_555 yes
C(123) C(122) C(22) H(22C) 179.79(6) 1_555 1_555 1_555 1_555 yes
C(122) C(123) C(124) N(125) -0.66(4) 1_555 1_555 1_555 1_555 yes
C(122) C(123) C(124) H(124) 178.63(7) 1_555 1_555 1_555 1_555 yes
C(122) C(123) C(23) H(23A) 175.35(7) 1_555 1_555 1_555 1_555 yes
C(122) C(123) C(23) H(23B) 61.43(5) 1_555 1_555 1_555 1_555 yes
C(122) C(123) C(23) H(23C) -59.03(5) 1_555 1_555 1_555 1_555 yes
C(23) C(123) C(124) N(125) 179.56(7) 1_555 1_555 1_555 1_555 yes
C(23) C(123) C(124) H(124) -1.16(4) 1_555 1_555 1_555 1_555 yes
C(124) C(123) C(23) H(23A) -4.87(4) 1_555 1_555 1_555 1_555 yes
C(124) C(123) C(23) H(23B) -118.79(6) 1_555 1_555 1_555 1_555 yes
C(124) C(123) C(23) H(23C) 120.75(6) 1_555 1_555 1_555 1_555 yes
CL(1) C(111) C(112) O(2) -2.01(4) 1_555 1_555 1_555 1_555 yes
CL(1) C(111) C(116) O(6) -2.25(4) 1_555 1_555 1_555 1_555 yes
CL(1) C(111) C(116) C(115) 177.16(5) 1_555 1_555 1_555 1_555 yes
C(116) C(111) C(112) O(2) 173.88(7) 1_555 1_555 1_555 1_555 yes
C(112) C(111) C(116) O(6) -178.18(7) 1_555 1_555 1_555 1_555 yes
C(112) C(111) C(116) C(115) 1.23(3) 1_555 1_555 1_555 1_555 yes
O(3) C(113) C(114) CL(2) -4.25(4) 1_555 1_555 1_555 1_555 yes
O(3) C(113) C(114) C(115) 173.79(6) 1_555 1_555 1_555 1_555 yes
CL(2) C(114) C(115) O(5) 0.28(4) 1_555 1_555 1_555 1_555 yes
CL(2) C(114) C(115) C(116) 179.65(5) 1_555 1_555 1_555 1_555 yes
C(113) C(114) C(115) O(5) -177.68(6) 1_555 1_555 1_555 1_555 yes
C(113) C(114) C(115) C(116) 1.68(3) 1_555 1_555 1_555 1_555 yes
O(5) C(115) C(116) O(6) 0.21(4) 1_555 1_555 1_555 1_555 yes
O(5) C(115) C(116) C(111) -179.26(5) 1_555 1_555 1_555 1_555 yes
C(114) C(115) C(116) O(6) -179.19(6) 1_555 1_555 1_555 1_555 yes
C(114) C(115) C(116) C(111) 1.34(4) 1_555 1_555 1_555 1_555 yes
####################################################################### 
# 
# 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_2_(3,4)_shelx
_database_code_depnum_ccdc_archive 'CCDC 1478093'
_audit_update_record             
;
2016-05-04 deposited with the CCDC.
2016-06-13 downloaded from the CCDC.
;

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         
;
C6 Cl2 O4, 2(C7 H10 N)  
;
_chemical_formula_sum            'C20 H20 Cl2 N2 O4'
_chemical_formula_weight         423.38
_chemical_compound_source        commercial

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14


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

_cell_length_a                   7.0429(2)
_cell_length_b                   9.3113(2)
_cell_length_c                   14.6210(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.3030(10)
_cell_angle_gamma                90
_cell_volume                     958.81(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    11674
_cell_measurement_theta_min      1
_cell_measurement_theta_max      53.87
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.18
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             440
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.369
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5265
_exptl_absorpt_correction_T_max  0.7502
_exptl_absorpt_process_details   'SADABS, Bruker(2001)'
#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      -0.0947379
_diffrn_orient_matrix_UB_21      -0.703941E-1
_diffrn_orient_matrix_UB_31      0.789320E-1
_diffrn_orient_matrix_UB_12      -0.689960E-1
_diffrn_orient_matrix_UB_22      0.5748E-3
_diffrn_orient_matrix_UB_32      -0.822995E-1
_diffrn_orient_matrix_UB_13      0.255391E-1
_diffrn_orient_matrix_UB_23      -0.595761E-1
_diffrn_orient_matrix_UB_33      -0.218269E-1
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_number            35670
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.59
_diffrn_reflns_theta_max         53.87
_diffrn_reflns_theta_full        53.87
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_reflns_number_total             11674
_reflns_number_gt                9999
_reflns_threshold_expression     >2σ(I)
_diffrn_reflns_reduction_process 
;
 Scaled and merged with Sortav
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0567P)²+0.0637P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         11674
_refine_ls_number_parameters     167
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0333
_refine_ls_wR_factor_ref         0.1065
_refine_ls_wR_factor_gt          0.1027
_refine_ls_goodness_of_fit_ref   1.07
_refine_ls_restrained_S_all      1.07
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.739
_refine_diff_density_min         -0.874
_refine_diff_density_rms         0.062

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.546363(14) 0.265138(11) 0.344060(7) 0.02126(2) Uani 1 1 d . . .
O3 O 0.76811(4) 0.70635(3) 0.52049(2) 0.01957(4) Uani 1 1 d . . .
O2 O 0.80876(4) 0.50837(4) 0.39103(2) 0.02042(5) Uani 1 1 d . . .
N125 N 1.09104(5) 0.71043(6) 0.41636(3) 0.02934(9) Uani 1 1 d . . .
C121 C 1.31979(6) 0.89354(5) 0.42535(3) 0.02063(6) Uani 1 1 d . . .
C122 C 1.42584(4) 0.82777(4) 0.35622(2) 0.01495(4) Uani 1 1 d . . .
C123 C 1.35435(5) 0.70233(4) 0.31488(3) 0.01861(5) Uani 1 1 d . . .
C124 C 1.18525(6) 0.64651(6) 0.34800(4) 0.02676(8) Uani 1 1 d . . .
C126 C 1.15300(6) 0.83204(6) 0.45515(3) 0.02723(9) Uani 1 1 d . . .
C22 C 1.61415(5) 0.88750(4) 0.32784(3) 0.01974(5) Uani 1 1 d . . .
C23 C 1.45375(9) 0.63032(6) 0.23722(4) 0.02899(9) Uani 1 1 d . . .
C111 C 0.52142(4) 0.39331(3) 0.42955(2) 0.01402(4) Uani 1 1 d . . .
C113 C 0.64002(4) 0.61374(3) 0.51459(2) 0.01357(4) Uani 1 1 d . . .
C112 C 0.66330(4) 0.49867(3) 0.43918(2) 0.01377(4) Uani 1 1 d . . .
H121 H 1.3552(14) 0.9810(12) 0.4532(7) 0.032(2) Uiso 1 1 d . . .
H124 H 1.1317(16) 0.5556(13) 0.3233(8) 0.038(3) Uiso 1 1 d . . .
H125 H 0.975(2) 0.6681(19) 0.4308(12) 0.076(5) Uiso 1 1 d . . .
H126 H 1.0701(15) 0.8696(12) 0.5017(8) 0.032(2) Uiso 1 1 d . . .
H21A H 1.391(2) 0.5342(16) 0.2191(11) 0.059(4) Uiso 1 1 d . . .
H21B H 1.5873(19) 0.6093(13) 0.2513(9) 0.045(3) Uiso 1 1 d . . .
H21C H 1.4501(19) 0.6932(15) 0.1835(9) 0.049(3) Uiso 1 1 d . . .
H22A H 1.7171(14) 0.8191(11) 0.3411(7) 0.026(2) Uiso 1 1 d . . .
H22B H 1.6186(16) 0.9032(11) 0.2628(8) 0.035(3) Uiso 1 1 d . . .
H22C H 1.6452(16) 0.9708(12) 0.3626(8) 0.036(3) Uiso 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 C111 1.7378(3) . ?
O3 C113 1.2506(4) . ?
O2 C112 1.2494(4) . ?
N125 C126 1.3385(9) . ?
N125 C124 1.3418(9) . ?
N125 H125 0.932(17) . ?
C121 C126 1.3795(6) . ?
C121 C122 1.4010(5) . ?
C121 H121 0.944(11) . ?
C122 C123 1.4071(5) . ?
C122 C22 1.4987(4) . ?
C123 C124 1.3889(6) . ?
C123 C23 1.4959(7) . ?
C124 H124 0.994(12) . ?
C126 H126 0.965(11) . ?
C22 H22A 0.984(10) . ?
C22 H22B 0.963(12) . ?
C22 H22C 0.952(12) . ?
C23 H21A 1.031(15) . ?
C23 H21B 0.981(13) . ?
C23 H21C 0.980(14) . ?
C111 C113 1.4050(4) 3_666 ?
C111 C112 1.4068(4) . ?
C113 C111 1.4050(4) 3_666 ?
C113 C112 1.5468(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
C126 N125 C124 121.97(3) . . ?
C126 N125 H125 123.1(11) . . ?
C124 N125 H125 114.7(11) . . ?
C126 C121 C122 120.30(4) . . ?
C126 C121 H121 116.5(6) . . ?
C122 C121 H121 123.2(6) . . ?
C121 C122 C123 118.80(3) . . ?
C121 C122 C22 120.90(3) . . ?
C123 C122 C22 120.29(3) . . ?
C124 C123 C122 117.81(4) . . ?
C124 C123 C23 120.17(4) . . ?
C122 C123 C23 122.03(4) . . ?
N125 C124 C123 121.47(4) . . ?
N125 C124 H124 117.4(7) . . ?
C123 C124 H124 121.1(7) . . ?
N125 C126 C121 119.58(4) . . ?
N125 C126 H126 114.1(7) . . ?
C121 C126 H126 126.3(7) . . ?
C122 C22 H22A 110.9(6) . . ?
C122 C22 H22B 111.3(7) . . ?
H22A C22 H22B 105.4(9) . . ?
C122 C22 H22C 110.8(7) . . ?
H22A C22 H22C 104.8(9) . . ?
H22B C22 H22C 113.3(9) . . ?
C123 C23 H21A 112.6(9) . . ?
C123 C23 H21B 112.5(8) . . ?
H21A C23 H21B 106.7(11) . . ?
C123 C23 H21C 109.3(8) . . ?
H21A C23 H21C 107.7(12) . . ?
H21B C23 H21C 107.9(10) . . ?
C113 C111 C112 123.43(3) 3_666 . ?
C113 C111 Cl1 118.11(2) 3_666 . ?
C112 C111 Cl1 118.45(2) . . ?
O3 C113 C111 125.30(3) . 3_666 ?
O3 C113 C112 116.59(3) . . ?
C111 C113 C112 118.11(2) 3_666 . ?
O2 C112 C111 125.32(3) . . ?
O2 C112 C113 116.22(3) . . ?
C111 C112 C113 118.46(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
C126 C121 C122 C123 3.13(6) . . . . ?
C126 C121 C122 C22 -175.56(4) . . . . ?
C121 C122 C123 C124 -2.85(5) . . . . ?
C22 C122 C123 C124 175.84(3) . . . . ?
C121 C122 C123 C23 176.61(4) . . . . ?
C22 C122 C123 C23 -4.69(5) . . . . ?
C126 N125 C124 C123 1.09(7) . . . . ?
C122 C123 C124 N125 0.82(6) . . . . ?
C23 C123 C124 N125 -178.66(4) . . . . ?
C124 N125 C126 C121 -0.86(7) . . . . ?
C122 C121 C126 N125 -1.28(6) . . . . ?
C113 C111 C112 O2 179.90(3) 3_666 . . . ?
Cl1 C111 C112 O2 -0.21(5) . . . . ?
C113 C111 C112 C113 -0.55(5) 3_666 . . . ?
Cl1 C111 C112 C113 179.34(2) . . . . ?
O3 C113 C112 O2 0.24(5) . . . . ?
C111 C113 C112 O2 -179.89(3) 3_666 . . . ?
O3 C113 C112 C111 -179.35(3) . . . . ?
C111 C113 C112 C111 0.52(5) 3_666 . . . ?

####################################################################### 
# 
# 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_2_(3,4)_xd
_database_code_depnum_ccdc_archive 'CCDC 1478094'
_audit_update_record             
;
2016-05-04 deposited with the CCDC.
2016-06-13 downloaded from the CCDC.
;

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         
;
C6 Cl2 O4, 2(C7 H10 N)  
;
_chemical_formula_sum            'C20 H20 Cl2 N2 O4'
_chemical_formula_weight         423.38
_chemical_compound_source        commercial

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14

loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 1/2+X,1/2-Y,1/2+Z

_cell_length_a                   7.0429(2)
_cell_length_b                   9.3113(2)
_cell_length_c                   14.6210(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.3030(10)
_cell_angle_gamma                90
_cell_volume                     958.81(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    11674
_cell_measurement_theta_min      1
_cell_measurement_theta_max      53.87
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.18
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             440
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.369
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5265
_exptl_absorpt_correction_T_max  0.7502
_exptl_absorpt_process_details   'SADABS, Bruker(2001)'
#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      -0.0947379
_diffrn_orient_matrix_UB_21      -0.703941E-1
_diffrn_orient_matrix_UB_31      0.789320E-1
_diffrn_orient_matrix_UB_12      -0.689960E-1
_diffrn_orient_matrix_UB_22      0.5748E-3
_diffrn_orient_matrix_UB_32      -0.822995E-1
_diffrn_orient_matrix_UB_13      0.255391E-1
_diffrn_orient_matrix_UB_23      -0.595761E-1
_diffrn_orient_matrix_UB_33      -0.218269E-1
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_number            35670
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.59
_diffrn_reflns_theta_max         53.87
_diffrn_reflns_theta_full        53.87
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_reflns_number_total             11674
_reflns_number_gt                9999
_reflns_threshold_expression     >2σ(I)
_diffrn_reflns_reduction_process 
;
 Scaled and merged with Sortav
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
        ?
;
_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
        calc w1 = 1/[s²(Fo)]
;
_refine_ls_extinction_method     'Becker-Coppens type 1 Lorentzian isotropic'
_refine_ls_extinction_expression 
;
        Becker, P.J. & Coppens, P. (1974) Acta Cryst., A30, 129-153.
;
_refine_ls_extinction_coef       0.06(2)
_refine_ls_number_reflns         10232
_refine_ls_number_parameters     379
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.034
_refine_ls_R_factor_gt           0.024
_refine_ls_wR_factor_ref         0.033
_refine_ls_goodness_of_fit_ref   2.046
_refine_ls_shift/su_max          0
_refine_diff_density_max         0.499
_refine_diff_density_min         -0.632
_refine_diff_density_rms         0.038

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, 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_symmetry_multiplicity
Cl(1) Cl 0.546388(11) 0.265125(9) 0.344080(5) 0.021 Uani 1 4
O(2) O 0.80852(4) 0.50842(4) 0.39105(2) 0.02 Uani 1 4
O(3) O 0.76795(4) 0.70640(4) 0.52044(2) 0.019 Uani 1 4
N(125) N 1.09073(5) 0.71167(7) 0.41714(4) 0.029 Uani 1 4
C(121) C 1.32000(5) 0.89358(4) 0.42538(2) 0.02 Uani 1 4
C(122) C 1.42592(4) 0.82772(3) 0.356184(18) 0.015 Uani 1 4
C(123) C 1.35426(4) 0.70237(4) 0.31491(2) 0.018 Uani 1 4
C(124) C 1.18492(6) 0.64659(5) 0.34820(3) 0.027 Uani 1 4
C(126) C 1.15325(5) 0.83256(6) 0.45539(3) 0.027 Uani 1 4
C(22) C 1.61404(4) 0.88740(4) 0.32777(2) 0.02 Uani 1 4
C(23) C 1.45356(8) 0.63023(5) 0.23732(3) 0.029 Uani 1 4
C(111) C 0.52148(3) 0.39330(3) 0.429550(16) 0.014 Uani 1 4
C(112) C 0.66327(3) 0.49866(3) 0.439182(16) 0.014 Uani 1 4
C(113) C 0.63995(3) 0.61373(3) 0.514554(16) 0.013 Uani 1 4
H(121) H 1.360487 0.994024 0.457334 0.036 Uani 1 4
H(124) H 1.12694 0.547539 0.321074 0.035 Uani 1 4
H(125) H 0.962569 0.663529 0.432341 0.031 Uani 1 4
H(126) H 1.059688 0.874337 0.507574 0.036 Uani 1 4
H(22A) H 1.72496 0.813864 0.342147 0.037 Uani 1 4
H(22B) H 1.619048 0.904823 0.25625 0.037 Uani 1 4
H(22C) H 1.648647 0.979972 0.36649 0.038 Uani 1 4
H(23A) H 1.389594 0.531525 0.218577 0.045 Uani 1 4
H(23B) H 1.597748 0.607666 0.252367 0.042 Uani 1 4
H(23C) H 1.449855 0.698212 0.179268 0.043 Uani 1 4

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl(1) 0.02162(3) 0.02094(3) 0.02090(3) -0.00847(2) 0.00767(2) -0.005346(19)
O(2) 0.01532(8) 0.02580(12) 0.01990(9) -0.00681(9) 0.00791(7) -0.00645(8)
O(3) 0.01656(9) 0.02115(10) 0.02062(10) -0.00544(8) 0.00566(8) -0.00769(8)
N(125) 0.01176(9) 0.0401(2) 0.03569(18) 0.02133(16) -0.00048(10) -0.00479(11)
C(121) 0.01824(10) 0.02367(12) 0.01959(10) 0.00179(9) 0.00594(8) 0.00186(9)
C(122) 0.01269(7) 0.01636(8) 0.01540(7) 0.00302(6) 0.00204(6) -0.00109(6)
C(123) 0.01713(9) 0.01908(10) 0.01906(9) 0.00253(8) -0.00380(7) -0.00305(8)
C(124) 0.01873(12) 0.02738(15) 0.03346(16) 0.01092(13) -0.00953(11)
-0.01016(11)
C(126) 0.01653(10) 0.03860(19) 0.02615(13) 0.01246(13) 0.00875(10) 0.00541(11)
C(22) 0.01592(9) 0.02017(11) 0.02273(11) 0.00351(8) 0.00513(8) -0.00335(8)
C(23) 0.0380(2) 0.02620(16) 0.02233(13) -0.00599(12) -0.00540(13) 0.00263(15)
C(111) 0.01298(7) 0.01456(7) 0.01409(7) -0.00176(6) 0.00318(5) -0.00182(6)
C(112) 0.01144(6) 0.01601(8) 0.01352(7) -0.00106(6) 0.00277(5) -0.00191(6)
C(113) 0.01176(7) 0.01502(8) 0.01357(7) -0.00066(6) 0.00232(5) -0.00225(6)
H(121) 0.030654 0.034185 0.043571 -0.008964 0.009619 -0.010811
H(124) 0.033315 0.032076 0.039636 -0.006909 0.006823 -0.008728
H(125) 0.024189 0.033428 0.036766 -0.003082 0.007173 -0.008632
H(126) 0.028356 0.039361 0.039781 -0.009383 0.013674 -0.00815
H(22A) 0.026006 0.036376 0.048479 0.015734 0.002446 0.006981
H(22B) 0.032832 0.055164 0.02301 0.010173 0.000154 -0.005171
H(22C) 0.034218 0.037349 0.041088 -0.008598 0.007618 -0.008104
H(23A) 0.043134 0.040285 0.052741 -0.01262 0.014817 -0.01556
H(23B) 0.02633 0.05421 0.045245 -0.003784 0.002433 0.004809
H(23C) 0.049318 0.047168 0.031389 0.008438 0.007961 0.001867


#----------------------------------------------------------------------------#
#                   MULTIPOLE PARAMETERS                                     #
#----------------------------------------------------------------------------#

loop_
_atom_rho_multipole_atom_label
_atom_rho_multipole_coeff_Pv
_atom_rho_multipole_coeff_P00
_atom_rho_multipole_coeff_P11
_atom_rho_multipole_coeff_P1-1
_atom_rho_multipole_coeff_P10
_atom_rho_multipole_coeff_P20
_atom_rho_multipole_coeff_P21
_atom_rho_multipole_coeff_P2-1
_atom_rho_multipole_coeff_P22
_atom_rho_multipole_coeff_P2-2
_atom_rho_multipole_coeff_P30
_atom_rho_multipole_coeff_P31
_atom_rho_multipole_coeff_P3-1
_atom_rho_multipole_coeff_P32
_atom_rho_multipole_coeff_P3-2
_atom_rho_multipole_coeff_P33
_atom_rho_multipole_coeff_P3-3
_atom_rho_multipole_coeff_P40
_atom_rho_multipole_coeff_P41
_atom_rho_multipole_coeff_P4-1
_atom_rho_multipole_coeff_P42
_atom_rho_multipole_coeff_P4-2
_atom_rho_multipole_coeff_P43
_atom_rho_multipole_coeff_P4-3
_atom_rho_multipole_coeff_P44
_atom_rho_multipole_coeff_P4-4
_atom_rho_multipole_kappa
_atom_rho_multipole_kappa_prime0
_atom_rho_multipole_kappa_prime1
_atom_rho_multipole_kappa_prime2
_atom_rho_multipole_kappa_prime3
_atom_rho_multipole_kappa_prime4
Cl(1) 7.53(4) 0 -0.146(12) 0.015(13) -0.046(11) -0.133(15) 0.014(18) 0.057(17)
0.074(17) -0.064(18) 0.056(10) 0.097(10) -0.009(9) 0.056(10) 0.020(10)
-0.126(10) -0.001(10) 0.025(15) -0.014(13) -0.006(12) 0.005(14) -0.026(14)
0.004(14) 0.024(15) 0.002(14) -0.015(13) 0.987088 1 1 1 1 1
O(2) 6.099(18) 0 0.029(10) -0.017(9) -0.082(8) -0.030(9) 0.007(9) -0.001(8)
-0.099(10) 0.004(10) 0.023(9) -0.011(8) -0.001(7) 0.020(8) 0.000(8) -0.026(9)
-0.012(8) 0 0 0 0 0 0 0 0 0 0.992324 0.995197 0.995197 0.995197 0.995197
0.995197
O(3) 6.096(18) 0 -0.026(10) 0.018(9) -0.050(9) -0.021(9) -0.011(10) 0.019(9)
-0.079(10) 0.013(10) 0.010(9) 0.030(8) -0.006(8) 0.032(8) 0.007(8) -0.023(8)
0.018(9) 0 0 0 0 0 0 0 0 0 0.992324 0.995197 0.995197 0.995197 0.995197
0.995197
N(125) 5.09(3) 0 0.302(16) -0.212(13) -0.011(10) -0.036(12) -0.019(13)
-0.009(11) 0.012(14) 0.054(13) 0.031(12) -0.154(12) 0.092(10) -0.022(12)
0.024(12) 0.156(14) -0.238(15) 0 0 0 0 0 0 0 0 0 1.009762 1.071635 1.071635
1.071635 1.071635 1.071635
C(121) 4.10(4) 0 -0.002(13) 0.082(14) 0.010(13) -0.150(12) 0.009(11) -0.013(12)
0.000(12) 0.055(12) -0.001(13) 0.023(13) 0.023(13) 0.020(13) -0.005(12)
0.204(14) -0.023(14) 0 0 0 0 0 0 0 0 0 1.006347 1.020103 1.020103 1.020103
1.020103 1.020103
C(122) 3.94(3) 0 0.033(12) -0.015(12) 0.023(11) -0.172(11) 0.031(10) 0.002(10)
-0.009(11) 0.003(11) 0.006(13) 0.008(12) 0.023(11) -0.004(12) 0.009(12)
0.226(13) -0.017(13) 0 0 0 0 0 0 0 0 0 1.006347 1.020103 1.020103 1.020103
1.020103 1.020103
C(123) 4.05(3) 0 -0.033(13) -0.022(14) 0.020(12) -0.168(12) -0.041(11)
-0.045(11) -0.050(12) -0.043(12) 0.002(13) 0.032(13) 0.018(13) -0.011(13)
0.038(13) 0.282(15) -0.006(14) 0 0 0 0 0 0 0 0 0 1.006347 1.020103 1.020103
1.020103 1.020103 1.020103
C(124) 4.08(3) 0 0.149(14) -0.159(16) -0.033(13) -0.062(14) -0.020(12)
0.039(13) 0.019(14) 0.169(15) -0.009(15) -0.061(13) 0.105(15) 0.009(15)
0.000(15) 0.135(17) -0.119(17) 0 0 0 0 0 0 0 0 0 1.006347 1.020103 1.020103
1.020103 1.020103 1.020103
C(126) 4.29(4) 0 -0.061(14) 0.153(17) 0.020(13) -0.190(14) 0.014(12) -0.011(14)
0.088(14) -0.014(15) -0.013(16) 0.122(14) -0.064(15) -0.019(14) -0.039(16)
0.370(17) -0.063(17) 0 0 0 0 0 0 0 0 0 1.006347 1.020103 1.020103 1.020103
1.020103 1.020103
C(22) 4.08(6) 0 0.003(12) 0.028(12) 0.010(12) 0.009(11) -0.002(11) -0.007(11)
-0.033(10) -0.010(11) 0.163(14) -0.034(12) 0.010(13) -0.022(12) -0.018(12)
0.002(11) -0.145(12) 0 0 0 0 0 0 0 0 0 0.99261 1.022229 1.022229 1.022229
1.022229 1.022229
C(23) 4.44(6) 0 -0.060(14) 0.115(14) 0.094(14) 0.046(14) 0.032(13) -0.122(15)
0.057(13) 0.066(14) 0.185(17) 0.030(15) 0.008(14) 0.001(14) 0.014(14) 0.040(14)
-0.223(15) 0 0 0 0 0 0 0 0 0 0.99261 1.022229 1.022229 1.022229 1.022229
1.022229
C(111) 4.14(3) 0 0.021(13) -0.055(13) 0.023(12) -0.025(11) -0.001(11)
-0.001(10) 0.063(11) 0.067(11) -0.003(13) 0.021(12) -0.062(12) 0.005(13)
-0.012(13) 0.245(13) -0.038(14) 0 0 0 0 0 0 0 0 0 0.990394 0.958702 0.958702
0.958702 0.958702 0.958702
C(112) 3.99(3) 0 -0.063(13) -0.027(13) 0.018(12) -0.204(12) 0.005(11) 0.014(11)
-0.081(12) 0.021(12) -0.019(13) -0.008(12) 0.024(12) 0.004(12) -0.017(13)
0.319(14) 0.050(14) 0 0 0 0 0 0 0 0 0 0.990394 0.958702 0.958702 0.958702
0.958702 0.958702
C(113) 4.15(3) 0 0.058(12) -0.008(13) -0.032(12) -0.235(12) 0.002(11) 0.004(11)
0.060(11) 0.042(11) -0.011(13) -0.018(12) -0.013(12) 0.001(13) 0.008(12)
0.312(14) -0.058(14) 0 0 0 0 0 0 0 0 0 0.990394 0.958702 0.958702 0.958702
0.958702 0.958702
H(121) 0.760(13) 0 0.022(9) -0.036(8) 0.115(10) -0.025(14) 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0 0 1.180144 1.180144 1.180144 1.180144 1.180144 1.180144
H(124) 0.760(13) 0 0.022(9) -0.036(8) 0.115(10) -0.025(14) 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0 0 1.180144 1.180144 1.180144 1.180144 1.180144 1.180144
H(125) 0.598(19) 0 0.052(14) -0.002(14) 0.100(15) -0.01(2) 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0 0 1.180144 1.180144 1.180144 1.180144 1.180144 1.180144
H(126) 0.760(13) 0 0.022(9) -0.036(8) 0.115(10) -0.025(14) 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0 0 1.180144 1.180144 1.180144 1.180144 1.180144 1.180144
H(22A) 0.910(14) 0 0.010(9) -0.052(9) 0.116(10) 0.064(14) 0 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0 1.168547 1.168547 1.168547 1.168547 1.168547 1.168547
H(22B) 0.910(14) 0 0.010(9) -0.052(9) 0.116(10) 0.064(14) 0 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0 1.168547 1.168547 1.168547 1.168547 1.168547 1.168547
H(22C) 0.910(14) 0 0.010(9) -0.052(9) 0.116(10) 0.064(14) 0 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0 1.168547 1.168547 1.168547 1.168547 1.168547 1.168547
H(23A) 0.775(16) 0 0.066(10) -0.005(9) 0.032(11) -0.004(14) 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0 0 1.168547 1.168547 1.168547 1.168547 1.168547 1.168547
H(23B) 0.775(16) 0 0.066(10) -0.005(9) 0.032(11) -0.004(14) 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0 0 1.168547 1.168547 1.168547 1.168547 1.168547 1.168547
H(23C) 0.775(16) 0 0.066(10) -0.005(9) 0.032(11) -0.004(14) 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0 0 1.168547 1.168547 1.168547 1.168547 1.168547 1.168547

loop_
_atom_local_axes_atom_label
_atom_local_axes_atom0
_atom_local_axes_ax1
_atom_local_axes_atom1
_atom_local_axes_atom2
_atom_local_axes_ax2
CL(1) C(111) Z CL(1) C(112) Y
O(2) C(112) Z O(2) H(125) Y
O(3) C(113) Z O(3) H(125) Y
N(125) C(124) X N(125) C(126) Y
C(121) C(122) X C(121) C(126) Y
C(122) C(121) X C(122) C(123) Y
C(123) C(124) X C(123) C(122) Y
C(124) C(123) X C(124) N(125) Y
C(126) C(121) X C(126) N(125) Y
C(22) H(22C) Z C(22) H(22B) Y
C(23) H(23C) Z C(23) H(23B) Y
C(111) C(112) X C(111) CL(1) Y
C(112) C(113) X C(112) C(111) Y
C(113) O(3) X C(113) C(112) Y
H(121) C(121) Z H(121) C(126) Y
H(124) C(124) Z H(124) N(125) Y
H(125) N(125) Z H(125) C(124) Y
H(126) C(126) Z H(126) N(125) Y
H(22A) C(22) Z H(22A) H(22C) Y
H(22B) C(22) Z H(22B) H(22A) Y
H(22C) C(22) Z H(22C) H(22A) Y
H(23A) C(23) Z H(23A) H(23B) Y
H(23B) C(23) Z H(23B) H(23C) Y
H(23C) C(23) Z H(23C) H(23B) Y


#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
CL(1) C(111) 1.7375(2) 1_555 1_555 yes
O(2) C(112) 1.2480(3) 1_555 1_555 yes
O(3) C(113) 1.2505(4) 1_555 1_555 yes
N(125) C(124) 1.3530(9) 1_555 1_555 yes
N(125) C(126) 1.3308(9) 1_555 1_555 yes
N(125) H(125) 1.0330(3) 1_555 1_555 yes
C(121) C(122) 1.4015(4) 1_555 1_555 yes
C(121) C(126) 1.3785(5) 1_555 1_555 yes
C(121) H(121) 1.0830(4) 1_555 1_555 yes
C(122) C(123) 1.4064(4) 1_555 1_555 yes
C(122) C(22) 1.4975(4) 1_555 1_555 yes
C(123) C(124) 1.3910(5) 1_555 1_555 yes
C(123) C(23) 1.4953(6) 1_555 1_555 yes
C(124) H(124) 1.0830(5) 1_555 1_555 yes
C(126) H(126) 1.0830(4) 1_555 1_555 yes
C(22) H(22A) 1.0590(3) 1_555 1_555 yes
C(22) H(22B) 1.0590(3) 1_555 1_555 yes
C(22) H(22C) 1.0590(4) 1_555 1_555 yes
C(23) H(23A) 1.0590(5) 1_555 1_555 yes
C(23) H(23B) 1.0590(6) 1_555 1_555 yes
C(23) H(23C) 1.0590(5) 1_555 1_555 yes
C(111) C(112) 1.4064(3) 1_555 1_555 yes
C(111) C(113) 1.4052(3) 1_555 3_666 yes

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C(124) N(125) C(126) 121.97(3) 1_555 1_555 1_555 yes
C(124) N(125) H(125) 113.47(7) 1_555 1_555 1_555 yes
C(126) N(125) H(125) 124.35(7) 1_555 1_555 1_555 yes
C(122) C(121) C(126) 120.47(4) 1_555 1_555 1_555 yes
C(122) C(121) H(121) 123.33(3) 1_555 1_555 1_555 yes
C(126) C(121) H(121) 116.19(3) 1_555 1_555 1_555 yes
C(121) C(122) C(123) 118.79(3) 1_555 1_555 1_555 yes
C(121) C(122) C(22) 120.86(3) 1_555 1_555 1_555 yes
C(123) C(122) C(22) 120.33(3) 1_555 1_555 1_555 yes
C(122) C(123) C(124) 117.79(4) 1_555 1_555 1_555 yes
C(122) C(123) C(23) 122.01(3) 1_555 1_555 1_555 yes
C(124) C(123) C(23) 120.20(4) 1_555 1_555 1_555 yes
N(125) C(124) C(123) 121.20(4) 1_555 1_555 1_555 yes
N(125) C(124) H(124) 117.96(4) 1_555 1_555 1_555 yes
C(123) C(124) H(124) 120.81(5) 1_555 1_555 1_555 yes
N(125) C(126) C(121) 119.70(4) 1_555 1_555 1_555 yes
N(125) C(126) H(126) 113.49(4) 1_555 1_555 1_555 yes
C(121) C(126) H(126) 126.78(5) 1_555 1_555 1_555 yes
C(122) C(22) H(22A) 110.97(3) 1_555 1_555 1_555 yes
C(122) C(22) H(22B) 111.40(3) 1_555 1_555 1_555 yes
C(122) C(22) H(22C) 110.81(3) 1_555 1_555 1_555 yes
H(22A) C(22) H(22B) 105.47(3) 1_555 1_555 1_555 yes
H(22A) C(22) H(22C) 104.64(3) 1_555 1_555 1_555 yes
H(22B) C(22) H(22C) 113.23(3) 1_555 1_555 1_555 yes
C(123) C(23) H(23A) 112.71(5) 1_555 1_555 1_555 yes
C(123) C(23) H(23B) 112.54(3) 1_555 1_555 1_555 yes
C(123) C(23) H(23C) 109.27(4) 1_555 1_555 1_555 yes
H(23A) C(23) H(23B) 106.72(4) 1_555 1_555 1_555 yes
H(23A) C(23) H(23C) 107.62(4) 1_555 1_555 1_555 yes
H(23B) C(23) H(23C) 107.74(5) 1_555 1_555 1_555 yes
CL(1) C(111) C(112) 118.477(17) 1_555 1_555 1_555 yes
CL(1) C(111) C(113) 118.123(18) 1_555 1_555 3_666 yes
C(112) C(111) C(113) 123.40(2) 1_555 1_555 3_666 yes
O(2) C(112) C(111) 125.31(3) 1_555 1_555 1_555 yes
O(3) C(113) C(111) 125.26(2) 1_555 1_555 3_666 yes

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
C(124) N(125) C(126) C(121) -0.83(5) 1_555 1_555 1_555 1_555 yes
C(126) N(125) C(124) C(123) 1.03(5) 1_555 1_555 1_555 1_555 yes
C(126) N(125) C(124) H(124) 179.03(8) 1_555 1_555 1_555 1_555 yes
C(124) N(125) C(126) H(126) 177.43(8) 1_555 1_555 1_555 1_555 yes
H(125) N(125) C(124) C(123) 175.96(7) 1_555 1_555 1_555 1_555 yes
H(125) N(125) C(124) H(124) -6.03(4) 1_555 1_555 1_555 1_555 yes
H(125) N(125) C(126) C(121) -175.21(8) 1_555 1_555 1_555 1_555 yes
H(125) N(125) C(126) H(126) 3.06(5) 1_555 1_555 1_555 1_555 yes
C(122) C(121) C(126) N(125) -1.27(4) 1_555 1_555 1_555 1_555 yes
C(126) C(121) C(122) C(123) 3.12(3) 1_555 1_555 1_555 1_555 yes
C(126) C(121) C(122) C(22) -175.59(5) 1_555 1_555 1_555 1_555 yes
C(122) C(121) C(126) H(126) -179.28(7) 1_555 1_555 1_555 1_555 yes
H(121) C(121) C(122) C(123) -175.75(5) 1_555 1_555 1_555 1_555 yes
H(121) C(121) C(122) C(22) 5.54(3) 1_555 1_555 1_555 1_555 yes
H(121) C(121) C(126) N(125) 177.68(6) 1_555 1_555 1_555 1_555 yes
H(121) C(121) C(126) H(126) -0.33(4) 1_555 1_555 1_555 1_555 yes
C(121) C(122) C(123) C(124) -2.87(3) 1_555 1_555 1_555 1_555 yes
C(121) C(122) C(123) C(23) 176.68(5) 1_555 1_555 1_555 1_555 yes
C(121) C(122) C(22) H(22A) 115.97(4) 1_555 1_555 1_555 1_555 yes
C(121) C(122) C(22) H(22B) -126.84(4) 1_555 1_555 1_555 1_555 yes
C(121) C(122) C(22) H(22C) 0.18(3) 1_555 1_555 1_555 1_555 yes
C(22) C(122) C(123) C(124) 175.85(5) 1_555 1_555 1_555 1_555 yes
C(22) C(122) C(123) C(23) -4.60(3) 1_555 1_555 1_555 1_555 yes
C(123) C(122) C(22) H(22A) -62.72(3) 1_555 1_555 1_555 1_555 yes
C(123) C(122) C(22) H(22B) 54.47(3) 1_555 1_555 1_555 1_555 yes
C(123) C(122) C(22) H(22C) -178.51(4) 1_555 1_555 1_555 1_555 yes
C(122) C(123) C(124) N(125) 0.88(4) 1_555 1_555 1_555 1_555 yes
C(122) C(123) C(124) H(124) -177.07(6) 1_555 1_555 1_555 1_555 yes
C(122) C(123) C(23) H(23A) 173.95(6) 1_555 1_555 1_555 1_555 yes
C(122) C(123) C(23) H(23B) 53.19(4) 1_555 1_555 1_555 1_555 yes
C(122) C(123) C(23) H(23C) -66.45(4) 1_555 1_555 1_555 1_555 yes
C(23) C(123) C(124) N(125) -178.68(7) 1_555 1_555 1_555 1_555 yes
C(23) C(123) C(124) H(124) 3.36(4) 1_555 1_555 1_555 1_555 yes
C(124) C(123) C(23) H(23A) -6.51(4) 1_555 1_555 1_555 1_555 yes
C(124) C(123) C(23) H(23B) -127.27(6) 1_555 1_555 1_555 1_555 yes
C(124) C(123) C(23) H(23C) 113.10(5) 1_555 1_555 1_555 1_555 yes
CL(1) C(111) C(112) O(2) -0.18(3) 1_555 1_555 1_555 1_555 yes
C(113) C(111) C(112) O(2) 179.93(4) 3_666 1_555 1_555 1_555 yes
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_(3,5)_shelx
_database_code_depnum_ccdc_archive 'CCDC 1478095'
_audit_update_record             
;
2016-05-04 deposited with the CCDC.
2016-06-13 downloaded from the CCDC.
;

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         
;
C6 H Cl2 O4 , C7 H10 N,  
;
_chemical_formula_sum            'C13 H11 Cl2 N O4'
_chemical_formula_weight         316.13

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 21/a'
_space_group_name_Hall           '-P 2yab'
_space_group_IT_number           14

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

_cell_length_a                   11.3192(4)
_cell_length_b                   10.2762(4)
_cell_length_c                   11.7534(4)
_cell_angle_alpha                90
_cell_angle_beta                 100.198(2)
_cell_angle_gamma                90
_cell_volume                     1345.54(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    14184
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      50.39
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_diffrn    1.561
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.494
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5315
_exptl_absorpt_correction_T_max  0.7496
_exptl_absorpt_process_details   'SADABS, Bruker(2001)'

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      0.505839E-1
_diffrn_orient_matrix_UB_21      -0.705651E-1
_diffrn_orient_matrix_UB_31      -0.227891E-1
_diffrn_orient_matrix_UB_12      -0.257790E-1
_diffrn_orient_matrix_UB_22      0.115927E-1
_diffrn_orient_matrix_UB_32      -0.931167E-1
_diffrn_orient_matrix_UB_13      0.751992E-1
_diffrn_orient_matrix_UB_23      0.395686E-1
_diffrn_orient_matrix_UB_33      -0.158924E-2
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_number            14184
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.65
_diffrn_reflns_theta_max         50.39
_diffrn_reflns_theta_full        50.39
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_reflns_number_total             14184
_reflns_number_gt                11716
_reflns_threshold_expression     >2σ(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0401P)²+0.2334P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         14184
_refine_ls_number_parameters     256
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0336
_refine_ls_wR_factor_ref         0.0943
_refine_ls_wR_factor_gt          0.0891
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.649
_refine_diff_density_min         -0.529
_refine_diff_density_rms         0.065

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.358829(11) -0.149015(11) -0.328745(10) 0.01689(2) Uani 1 1 d . . .
Cl2 Cl 0.704366(12) -0.592147(12) -0.081771(11) 0.01908(2) Uani 1 1 d . . .
O2 O 0.48180(4) -0.15940(4) -0.08107(3) 0.01945(6) Uani 1 1 d . . .
O3 O 0.62539(4) -0.34909(4) 0.02079(3) 0.02024(6) Uani 1 1 d . . .
O5 O 0.60606(4) -0.56558(4) -0.33406(3) 0.01826(6) Uani 1 1 d . . .
O6 O 0.45186(4) -0.38907(4) -0.43319(3) 0.01764(6) Uani 1 1 d . . .
N125 N 0.50603(4) -0.15333(4) 0.14998(3) 0.01542(5) Uani 1 1 d . . .
C121 C 0.37259(4) -0.06540(5) 0.26376(4) 0.01623(6) Uani 1 1 d . . .
C122 C 0.45004(4) -0.11042(5) 0.36169(4) 0.01712(7) Uani 1 1 d . . .
C123 C 0.55755(4) -0.17385(5) 0.35330(4) 0.01600(6) Uani 1 1 d . . .
C124 C 0.58285(4) -0.19426(5) 0.24339(4) 0.01599(6) Uani 1 1 d . . .
C126 C 0.40412(4) -0.08996(5) 0.15680(4) 0.01586(6) Uani 1 1 d . . .
C21 C 0.26018(5) 0.01014(7) 0.27008(6) 0.02466(10) Uani 1 1 d . . .
C23 C 0.64485(6) -0.21832(7) 0.45754(5) 0.02462(10) Uani 1 1 d . . .
C111 C 0.46123(4) -0.26330(4) -0.26276(3) 0.01360(5) Uani 1 1 d . . .
C112 C 0.50502(4) -0.25075(4) -0.14358(3) 0.01396(5) Uani 1 1 d . . .
C113 C 0.58724(4) -0.35984(4) -0.08305(4) 0.01430(6) Uani 1 1 d . . .
C114 C 0.61567(4) -0.46947(4) -0.15149(4) 0.01457(6) Uani 1 1 d . . .
C115 C 0.57587(4) -0.47169(4) -0.26753(4) 0.01387(5) Uani 1 1 d . . .
C116 C 0.49088(4) -0.36922(4) -0.32831(3) 0.01327(5) Uani 1 1 d . . .
H122 H 0.4323(11) -0.0936(12) 0.4399(11) 0.029(3) Uiso 1 1 d . . .
H124 H 0.6545(10) -0.2341(11) 0.2295(9) 0.021(2) Uiso 1 1 d . . .
H125 H 0.5235(12) -0.1680(13) 0.0803(12) 0.037(3) Uiso 1 1 d . . .
H126 H 0.3570(10) -0.0658(12) 0.0860(10) 0.025(3) Uiso 1 1 d . . .
H21A H 0.2325(12) -0.0050(15) 0.3422(12) 0.041(3) Uiso 1 1 d . . .
H21B H 0.2747(12) 0.1009(14) 0.2657(12) 0.038(3) Uiso 1 1 d . . .
H21C H 0.1988(13) -0.0080(15) 0.2049(12) 0.042(4) Uiso 1 1 d . . .
H23A H 0.7215(13) -0.1913(15) 0.4541(13) 0.046(4) Uiso 1 1 d . . .
H23B H 0.6474(13) -0.3146(16) 0.4621(13) 0.048(4) Uiso 1 1 d . . .
H23C H 0.6175(12) -0.1895(14) 0.5284(12) 0.043(4) Uiso 1 1 d . . .
H5 H 0.5713(12) -0.5513(14) -0.4068(12) 0.040(4) Uiso 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 C111 1.7337(5) . ?
Cl2 C114 1.7255(5) . ?
O2 C112 1.2484(5) . ?
O3 C113 1.2254(5) . ?
O5 C115 1.3244(5) . ?
O5 H5 0.888(14) . ?
O6 C116 1.2503(5) . ?
N125 C126 1.3393(6) . ?
N125 C124 1.3418(6) . ?
N125 H125 0.889(13) . ?
C121 C126 1.3893(7) . ?
C121 C122 1.3964(7) . ?
C121 C21 1.5035(7) . ?
C122 C123 1.3993(7) . ?
C122 H122 0.990(13) . ?
C123 C124 1.3877(6) . ?
C123 C23 1.5026(7) . ?
C124 H124 0.948(11) . ?
C126 H126 0.939(11) . ?
C21 H21A 0.967(14) . ?
C21 H21B 0.950(14) . ?
C21 H21C 0.957(14) . ?
C23 H23A 0.919(14) . ?
C23 H23B 0.991(16) . ?
C23 H23C 0.984(14) . ?
C111 C112 1.4066(6) . ?
C111 C116 1.4081(6) . ?
C112 C113 1.5473(6) . ?
C113 C114 1.4531(6) . ?
C114 C115 1.3587(6) . ?
C115 C116 1.5170(6) . ?

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
C115 O5 H5 109.4(9) . . ?
C126 N125 C124 122.94(4) . . ?
C126 N125 H125 118.2(9) . . ?
C124 N125 H125 118.9(9) . . ?
C126 C121 C122 117.47(4) . . ?
C126 C121 C21 119.58(5) . . ?
C122 C121 C21 122.93(5) . . ?
C121 C122 C123 121.54(4) . . ?
C121 C122 H122 120.5(7) . . ?
C123 C122 H122 117.9(7) . . ?
C124 C123 C122 117.48(4) . . ?
C124 C123 C23 119.91(5) . . ?
C122 C123 C23 122.61(5) . . ?
N125 C124 C123 120.24(4) . . ?
N125 C124 H124 116.4(7) . . ?
C123 C124 H124 123.3(7) . . ?
N125 C126 C121 120.29(4) . . ?
N125 C126 H126 115.8(7) . . ?
C121 C126 H126 123.9(7) . . ?
C121 C21 H21A 111.6(8) . . ?
C121 C21 H21B 110.4(8) . . ?
H21A C21 H21B 106.9(12) . . ?
C121 C21 H21C 111.1(8) . . ?
H21A C21 H21C 111.6(11) . . ?
H21B C21 H21C 104.9(12) . . ?
C123 C23 H23A 111.2(9) . . ?
C123 C23 H23B 110.9(9) . . ?
H23A C23 H23B 106.6(13) . . ?
C123 C23 H23C 109.8(8) . . ?
H23A C23 H23C 112.8(12) . . ?
H23B C23 H23C 105.3(12) . . ?
C112 C111 C116 122.66(4) . . ?
C112 C111 Cl1 118.24(3) . . ?
C116 C111 Cl1 118.95(3) . . ?
O2 C112 C111 125.53(4) . . ?
O2 C112 C113 116.51(4) . . ?
C111 C112 C113 117.95(4) . . ?
O3 C113 C114 123.21(4) . . ?
O3 C113 C112 118.02(4) . . ?
C114 C113 C112 118.77(4) . . ?
C115 C114 C113 120.14(4) . . ?
C115 C114 Cl2 121.74(3) . . ?
C113 C114 Cl2 118.09(3) . . ?
O5 C115 C114 122.05(4) . . ?
O5 C115 C116 115.85(4) . . ?
C114 C115 C116 122.07(4) . . ?
O6 C116 C111 126.07(4) . . ?
O6 C116 C115 115.78(4) . . ?
C111 C116 C115 118.14(4) . . ?

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
C126 C121 C122 C123 2.21(7) . . . . ?
C21 C121 C122 C123 -176.21(5) . . . . ?
C121 C122 C123 C124 -2.00(7) . . . . ?
C121 C122 C123 C23 177.42(5) . . . . ?
C126 N125 C124 C123 1.22(8) . . . . ?
C122 C123 C124 N125 0.29(7) . . . . ?
C23 C123 C124 N125 -179.15(5) . . . . ?
C124 N125 C126 C121 -1.00(8) . . . . ?
C122 C121 C126 N125 -0.71(7) . . . . ?
C21 C121 C126 N125 177.77(5) . . . . ?
C116 C111 C112 O2 -179.90(5) . . . . ?
Cl1 C111 C112 O2 -4.32(7) . . . . ?
C116 C111 C112 C113 -1.07(6) . . . . ?
Cl1 C111 C112 C113 174.51(3) . . . . ?
O2 C112 C113 O3 -1.01(7) . . . . ?
C111 C112 C113 O3 -179.95(5) . . . . ?
O2 C112 C113 C114 179.09(4) . . . . ?
C111 C112 C113 C114 0.15(6) . . . . ?
O3 C113 C114 C115 -176.27(5) . . . . ?
C112 C113 C114 C115 3.62(7) . . . . ?
O3 C113 C114 Cl2 1.73(7) . . . . ?
C112 C113 C114 Cl2 -178.38(3) . . . . ?
C113 C114 C115 O5 175.62(4) . . . . ?
Cl2 C114 C115 O5 -2.30(7) . . . . ?
C113 C114 C115 C116 -6.41(7) . . . . ?
Cl2 C114 C115 C116 175.67(3) . . . . ?
C112 C111 C116 O6 177.16(5) . . . . ?
Cl1 C111 C116 O6 1.61(6) . . . . ?
C112 C111 C116 C115 -1.46(6) . . . . ?
Cl1 C111 C116 C115 -177.00(3) . . . . ?
O5 C115 C116 O6 4.74(6) . . . . ?
C114 C115 C116 O6 -173.34(4) . . . . ?
O5 C115 C116 C111 -176.50(4) . . . . ?
C114 C115 C116 C111 5.41(6) . . . . ?

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

data_1_(3,5)_xd
_database_code_depnum_ccdc_archive 'CCDC 1478096'
_audit_update_record             
;
2016-05-04 deposited with the CCDC.
2016-06-13 downloaded from the CCDC.
;

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         
;
C6 H Cl2 O4 , C7 H10 N,  
;
_chemical_formula_sum            'C13 H11 Cl2 N O4'
_chemical_formula_weight         316.13

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 21/a'
_space_group_name_Hall           '-P 2yab'
_space_group_IT_number           14


loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,-Z
3 -X,-Y,-Z
4 1/2+X,1/2-Y,+Z

_cell_length_a                   11.3192(4)
_cell_length_b                   10.2762(4)
_cell_length_c                   11.7534(4)
_cell_angle_alpha                90
_cell_angle_beta                 100.198(2)
_cell_angle_gamma                90
_cell_volume                     1345.54(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    14184
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      50.39
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_diffrn    1.561
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648
_exptl_special_details           
;
 ?
;


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.494
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5315
_exptl_absorpt_correction_T_max  0.7496
_exptl_absorpt_process_details   'SADABS, Bruker(2001)'

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      0.505839E-1
_diffrn_orient_matrix_UB_21      -0.705651E-1
_diffrn_orient_matrix_UB_31      -0.227891E-1
_diffrn_orient_matrix_UB_12      -0.257790E-1
_diffrn_orient_matrix_UB_22      0.115927E-1
_diffrn_orient_matrix_UB_32      -0.931167E-1
_diffrn_orient_matrix_UB_13      0.751992E-1
_diffrn_orient_matrix_UB_23      0.395686E-1
_diffrn_orient_matrix_UB_33      -0.158924E-2
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_number            14184
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.65
_diffrn_reflns_theta_max         50.39
_diffrn_reflns_theta_full        50.39
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_reflns_number_total             14184
_reflns_number_gt                11716
_reflns_threshold_expression     >2σ(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
        ?
;
_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
        calc w1 = 1/[s²(Fo)]
;
_refine_ls_extinction_method     none
_refine_ls_number_reflns         12092
_refine_ls_number_parameters     542
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.043
_refine_ls_R_factor_gt           0.026
_refine_ls_wR_factor_ref         0.028
_refine_ls_goodness_of_fit_ref   1.575
_refine_ls_shift/su_max          0
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.053

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, 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_symmetry_multiplicity
Cl(1) Cl 0.358829(8) -0.149016(8) -0.328769(7) 0.017 Uani 1 4
Cl(2) Cl 0.704349(8) -0.592158(8) -0.081767(7) 0.019 Uani 1 4
O(2) O 0.48191(5) -0.15937(4) -0.08116(3) 0.019 Uani 1 4
O(3) O 0.62551(4) -0.34894(5) 0.02080(3) 0.02 Uani 1 4
O(5) O 0.60593(4) -0.56543(4) -0.33422(4) 0.018 Uani 1 4
O(6) O 0.45183(4) -0.38899(4) -0.43313(3) 0.017 Uani 1 4
N(125) N 0.50603(3) -0.15335(4) 0.14991(3) 0.015 Uani 1 4
C(121) C 0.37253(3) -0.06543(4) 0.26373(3) 0.016 Uani 1 4
C(122) C 0.44998(3) -0.11039(4) 0.36179(3) 0.017 Uani 1 4
C(123) C 0.55757(3) -0.17388(4) 0.35335(3) 0.016 Uani 1 4
C(124) C 0.58286(3) -0.19427(4) 0.24328(3) 0.016 Uani 1 4
C(126) C 0.40417(3) -0.08993(4) 0.15666(3) 0.016 Uani 1 4
C(21) C 0.26016(4) 0.01009(5) 0.27000(5) 0.025 Uani 1 4
C(23) C 0.64468(4) -0.21816(6) 0.45749(4) 0.025 Uani 1 4
C(111) C 0.46119(3) -0.26325(3) -0.26274(3) 0.013 Uani 1 4
C(112) C 0.50502(3) -0.25071(3) -0.14363(3) 0.014 Uani 1 4
C(113) C 0.58723(3) -0.35983(3) -0.08308(3) 0.014 Uani 1 4
C(114) C 0.61573(3) -0.46949(3) -0.15141(3) 0.014 Uani 1 4
C(115) C 0.57586(3) -0.47184(3) -0.26754(3) 0.014 Uani 1 4
C(116) C 0.49085(3) -0.36917(3) -0.32832(3) 0.013 Uani 1 4
H(122) H 0.43064 -0.092036 0.447361 0.033 Uani 1 4
H(124) H 0.664732 -0.239767 0.22748 0.032 Uani 1 4
H(125) H 0.526307 -0.170413 0.068913 0.028 Uani 1 4
H(126) H 0.349722 -0.062024 0.075047 0.033 Uani 1 4
H(21A) H 0.229874 -0.006402 0.349015 0.042 Uani 1 4
H(21B) H 0.276392 0.111264 0.265245 0.042 Uani 1 4
H(21C) H 0.192236 -0.010002 0.197884 0.041 Uani 1 4
H(23A) H 0.733111 -0.187223 0.45358 0.043 Uani 1 4
H(23B) H 0.647518 -0.32104 0.462404 0.041 Uani 1 4
H(23C) H 0.615334 -0.187305 0.533831 0.041 Uani 1 4
H(5) H 0.567887 -0.549844 -0.414063 0.028 Uani 1 4



#----------------------------------------------------------------------------#
#                   MULTIPOLE PARAMETERS                                     #
#----------------------------------------------------------------------------#

loop_
_atom_rho_multipole_atom_label
_atom_rho_multipole_coeff_Pv
_atom_rho_multipole_coeff_P00
_atom_rho_multipole_coeff_P11
_atom_rho_multipole_coeff_P1-1
_atom_rho_multipole_coeff_P10
_atom_rho_multipole_coeff_P20
_atom_rho_multipole_coeff_P21
_atom_rho_multipole_coeff_P2-1
_atom_rho_multipole_coeff_P22
_atom_rho_multipole_coeff_P2-2
_atom_rho_multipole_coeff_P30
_atom_rho_multipole_coeff_P31
_atom_rho_multipole_coeff_P3-1
_atom_rho_multipole_coeff_P32
_atom_rho_multipole_coeff_P3-2
_atom_rho_multipole_coeff_P33
_atom_rho_multipole_coeff_P3-3
_atom_rho_multipole_coeff_P40
_atom_rho_multipole_coeff_P41
_atom_rho_multipole_coeff_P4-1
_atom_rho_multipole_coeff_P42
_atom_rho_multipole_coeff_P4-2
_atom_rho_multipole_coeff_P43
_atom_rho_multipole_coeff_P4-3
_atom_rho_multipole_coeff_P44
_atom_rho_multipole_coeff_P4-4
_atom_rho_multipole_kappa
_atom_rho_multipole_kappa_prime0
_atom_rho_multipole_kappa_prime1
_atom_rho_multipole_kappa_prime2
_atom_rho_multipole_kappa_prime3
_atom_rho_multipole_kappa_prime4
Cl(1) 7.29(3) 0 0.014(12) -0.006(11) -0.006(12) -0.175(14) -0.002(15) 0.018(15)
-0.001(14) -0.004(15) 0.061(10) 0.008(9) -0.033(9) 0.043(10) -0.018(10)
0.011(9) -0.027(9) -0.025(14) 0.024(12) -0.002(12) -0.012(13) 0.069(13)
0.011(12) -0.004(13) 0.029(12) 0.014(12) 0.984845 1 1 1 1 1
Cl(2) 7.32(3) 0 0.010(12) 0.008(12) -0.003(12) -0.180(14) 0.001(15) 0.023(15)
-0.027(14) 0.016(15) 0.052(11) -0.009(10) 0.002(10) 0.074(10) -0.006(10)
0.050(10) 0.008(10) -0.045(15) -0.014(13) -0.020(13) 0.004(13) -0.071(14)
-0.001(13) 0.004(13) 0.029(13) -0.008(12) 0.984845 1 1 1 1 1
O(2) 6.037(19) 0 -0.037(11) 0.013(10) -0.063(10) -0.003(11) 0.018(11)
-0.003(10) -0.089(11) 0.016(11) 0.004(9) 0.006(9) 0.007(8) 0.037(9) 0.003(9)
-0.018(9) 0.005(9) 0 0 0 0 0 0 0 0 0 0.993953 1.017439 1.017439 1.017439
1.017439 1.017439
O(3) 6.042(18) 0 0.042(12) 0.007(10) -0.029(10) 0.003(12) -0.010(11) 0.009(10)
-0.115(11) -0.010(11) -0.002(10) -0.028(9) 0.016(8) 0.045(8) 0.012(9) 0.022(9)
-0.017(9) 0 0 0 0 0 0 0 0 0 0.993953 1.017439 1.017439 1.017439 1.017439
1.017439
O(5) 6.00(2) 0 0.008(10) -0.061(10) -0.044(12) -0.006(12) -0.005(10) 0.000(10)
0.027(11) 0.014(10) 0.070(9) -0.002(8) -0.028(8) 0.052(8) -0.011(8) 0.002(8)
0.013(8) 0 0 0 0 0 0 0 0 0 0.995367 1.049962 1.049962 1.049962 1.049962
1.049962
O(6) 6.083(19) 0 -0.009(10) 0.031(10) -0.043(10) 0.000(11) 0.003(10) 0.003(10)
-0.086(11) -0.001(11) 0.015(9) -0.007(8) -0.020(8) 0.010(8) -0.015(8) 0.002(8)
0.017(8) 0 0 0 0 0 0 0 0 0 0.993953 1.017439 1.017439 1.017439 1.017439
1.017439
N(125) 4.98(3) 0 0.000(13) -0.021(13) 0.003(11) -0.133(12) 0.012(10) 0.016(10)
-0.012(11) 0.011(12) -0.001(11) 0.016(11) 0.014(10) 0.041(11) 0.014(11)
0.189(11) 0.008(11) 0 0 0 0 0 0 0 0 0 0.99783 0.953516 0.953516 0.953516
0.953516 0.953516
C(121) 4.05(3) 0 0.030(15) 0.001(13) 0.004(12) -0.196(13) -0.010(12) -0.014(11)
0.006(13) 0.002(13) -0.006(14) -0.016(13) 0.016(13) 0.004(14) 0.007(13)
0.215(15) -0.047(15) 0 0 0 0 0 0 0 0 0 0.994872 0.980891 0.980891 0.980891
0.980891 0.980891
C(122) 4.07(4) 0 0.032(15) 0.044(15) -0.004(12) -0.198(13) 0.004(12) 0.020(12)
-0.011(14) -0.010(13) -0.015(14) 0.008(13) 0.022(12) 0.012(14) 0.005(13)
0.261(15) -0.003(15) 0 0 0 0 0 0 0 0 0 0.994872 0.980891 0.980891 0.980891
0.980891 0.980891
C(123) 4.00(3) 0 0.042(14) 0.018(14) 0.000(13) -0.203(13) -0.003(12) -0.009(12)
-0.009(13) 0.002(13) 0.012(14) 0.028(13) 0.036(13) 0.016(14) -0.012(14)
0.227(15) -0.002(15) 0 0 0 0 0 0 0 0 0 0.994872 0.980891 0.980891 0.980891
0.980891 0.980891
C(124) 4.04(3) 0 -0.044(14) 0.042(14) 0.010(13) -0.211(13) 0.012(12) 0.025(12)
-0.043(13) -0.014(13) 0.002(14) -0.016(13) 0.019(13) 0.016(13) -0.013(13)
0.271(14) 0.039(14) 0 0 0 0 0 0 0 0 0 0.994872 0.980891 0.980891 0.980891
0.980891 0.980891
C(126) 4.10(3) 0 -0.036(15) 0.017(15) 0.029(12) -0.222(13) -0.008(12)
-0.006(11) -0.034(13) -0.007(12) -0.021(14) 0.012(13) 0.015(12) 0.014(14)
0.013(13) 0.273(14) 0.042(14) 0 0 0 0 0 0 0 0 0 0.994872 0.980891 0.980891
0.980891 0.980891 0.980891
C(21) 4.34(6) 0 0.073(14) 0.001(16) -0.006(13) 0.022(14) 0.006(12) -0.015(13)
0.021(13) 0.002(14) 0.158(16) 0.043(16) -0.041(14) -0.036(14) -0.083(15)
0.005(14) -0.169(15) 0 0 0 0 0 0 0 0 0 0.98638 0.964707 0.964707 0.964707
0.964707 0.964707
C(23) 4.10(6) 0 0.040(15) -0.013(16) 0.065(14) 0.015(13) -0.009(12) -0.015(15)
-0.008(14) -0.004(14) 0.131(17) 0.004(15) -0.030(14) -0.072(15) -0.121(15)
0.026(15) -0.147(16) 0 0 0 0 0 0 0 0 0 0.98638 0.964707 0.964707 0.964707
0.964707 0.964707
C(111) 4.14(3) 0 0.042(13) 0.032(13) 0.010(12) -0.089(12) 0.000(11) 0.008(11)
0.037(12) -0.076(12) 0.024(13) 0.033(12) 0.064(12) 0.021(13) -0.023(12)
0.233(13) 0.021(14) 0 0 0 0 0 0 0 0 0 0.993058 0.981239 0.981239 0.981239
0.981239 0.981239
C(112) 3.99(3) 0 0.061(13) 0.012(13) 0.026(11) -0.243(12) -0.012(11) 0.014(11)
0.065(12) -0.056(12) 0.014(13) -0.019(12) 0.004(12) -0.021(12) 0.009(12)
0.295(14) 0.035(14) 0 0 0 0 0 0 0 0 0 0.993058 0.981239 0.981239 0.981239
0.981239 0.981239
C(113) 4.07(3) 0 0.089(14) 0.027(13) -0.016(12) -0.272(13) -0.015(11) 0.002(11)
0.074(13) -0.008(12) -0.007(13) -0.012(13) -0.006(12) 0.009(13) 0.003(13)
0.315(14) -0.006(14) 0 0 0 0 0 0 0 0 0 0.993058 0.981239 0.981239 0.981239
0.981239 0.981239
C(114) 4.12(3) 0 0.040(14) 0.019(13) 0.020(12) -0.093(12) 0.008(11) 0.011(11)
0.043(13) -0.025(12) 0.009(13) 0.039(13) 0.025(12) 0.010(13) 0.038(12)
0.242(14) -0.026(14) 0 0 0 0 0 0 0 0 0 0.993058 0.981239 0.981239 0.981239
0.981239 0.981239
C(115) 4.08(3) 0 -0.077(12) 0.007(14) 0.006(11) -0.240(12) 0.000(11) -0.001(11)
-0.042(13) -0.067(12) -0.003(13) -0.027(12) 0.013(12) 0.006(13) 0.002(13)
0.288(14) -0.008(14) 0 0 0 0 0 0 0 0 0 0.993058 0.981239 0.981239 0.981239
0.981239 0.981239
C(116) 4.05(3) 0 0.047(13) 0.016(13) -0.005(12) -0.239(12) 0.011(11) -0.008(11)
0.063(13) -0.071(12) 0.008(13) -0.020(12) 0.005(12) 0.007(13) -0.005(13)
0.297(14) 0.016(15) 0 0 0 0 0 0 0 0 0 0.993058 0.981239 0.981239 0.981239
0.981239 0.981239
H(122) 0.836(12) 0 -0.016(8) -0.009(7) 0.141(10) 0.063(12) 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0 0 1.197682 1.197682 1.197682 1.197682 1.197682 1.197682
H(124) 0.836(12) 0 -0.016(8) -0.009(7) 0.141(10) 0.063(12) 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0 0 1.197682 1.197682 1.197682 1.197682 1.197682 1.197682
H(125) 0.692(19) 0 -0.041(13) 0.060(12) 0.115(15) 0.11(2) 0 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0 1.197682 1.197682 1.197682 1.197682 1.197682 1.197682
H(126) 0.836(12) 0 -0.016(8) -0.009(7) 0.141(10) 0.063(12) 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0 0 1.197682 1.197682 1.197682 1.197682 1.197682 1.197682
H(21A) 0.872(15) 0 -0.017(9) -0.020(9) 0.086(10) -0.002(14) 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0 0 1.169181 1.169181 1.169181 1.169181 1.169181 1.169181
H(21B) 0.872(15) 0 -0.017(9) -0.020(9) 0.086(10) -0.002(14) 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0 0 1.169181 1.169181 1.169181 1.169181 1.169181 1.169181
H(21C) 0.872(15) 0 -0.017(9) -0.020(9) 0.086(10) -0.002(14) 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0 0 1.169181 1.169181 1.169181 1.169181 1.169181 1.169181
H(23A) 0.835(15) 0 -0.008(10) -0.002(9) 0.106(11) 0.031(14) 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0 0 1.169181 1.169181 1.169181 1.169181 1.169181 1.169181
H(23B) 0.835(15) 0 -0.008(10) -0.002(9) 0.106(11) 0.031(14) 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0 0 1.169181 1.169181 1.169181 1.169181 1.169181 1.169181
H(23C) 0.835(15) 0 -0.008(10) -0.002(9) 0.106(11) 0.031(14) 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 0 0 1.169181 1.169181 1.169181 1.169181 1.169181 1.169181
H(5) 0.775(18) 0 -0.041(12) 0.030(12) 0.183(16) 0.11(2) 0 0 0 0 0 0 0 0 0 0 0 0
0 0 0 0 0 0 0 0 1.188231 1.188231 1.188231 1.188231 1.188231 1.188231

loop_
_atom_local_axes_atom_label
_atom_local_axes_atom0
_atom_local_axes_ax1
_atom_local_axes_atom1
_atom_local_axes_atom2
_atom_local_axes_ax2
CL(1) C(111) Z CL(1) C(112) Y
CL(2) C(114) Z CL(2) C(115) Y
O(2) C(112) Z O(2) H(125) Y
O(3) C(113) Z O(3) H(125) Y
O(5) H(5) Z O(5) C(115) Y
O(6) C(116) Z O(6) H(5) Y
N(125) C(124) X N(125) C(126) Y
C(121) C(122) X C(121) C(123) Y
C(122) C(123) X C(122) C(121) Y
C(123) C(124) X C(123) C(122) Y
C(124) N(125) X C(124) C(123) Y
C(126) N(125) X C(126) C(121) Y
C(21) H(21C) Z C(21) H(21B) Y
C(23) H(23A) Z C(23) H(23B) Y
C(111) C(112) X C(111) C(116) Y
C(112) O(2) X C(112) C(111) Y
C(113) O(3) X C(113) C(114) Y
C(114) C(115) X C(114) C(113) Y
C(115) O(5) X C(115) C(114) Y
C(116) O(6) X C(116) C(111) Y
H(122) C(122) Z H(122) C(123) Y
H(124) C(124) Z H(124) N(125) Y
H(125) N(125) Z H(125) O(2) Y
H(126) C(126) Z H(126) N(125) Y
H(21A) C(21) Z H(21A) H(21B) Y
H(21B) C(21) Z H(21B) H(21C) Y
H(21C) C(21) Z H(21C) H(21B) Y
H(23A) C(23) Z H(23A) H(23B) Y
H(23B) C(23) Z H(23B) H(23A) Y
H(23C) C(23) Z H(23C) H(23B) Y
H(5) O(5) Z H(5) C(115) Y


#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
CL(1) C(111) 1.7333(3) 1_555 1_555 yes
CL(2) C(114) 1.7246(4) 1_555 1_555 yes
O(2) C(112) 1.2475(5) 1_555 1_555 yes
O(3) C(113) 1.2262(5) 1_555 1_555 yes
O(5) C(115) 1.3227(5) 1_555 1_555 yes
O(5) H(5) 0.9740(5) 1_555 1_555 yes
O(6) C(116) 1.2495(5) 1_555 1_555 yes
N(125) C(124) 1.3414(5) 1_555 1_555 yes
N(125) C(126) 1.3390(5) 1_555 1_555 yes
N(125) H(125) 1.0330(3) 1_555 1_555 yes
C(121) C(122) 1.3974(5) 1_555 1_555 yes
C(121) C(126) 1.3910(5) 1_555 1_555 yes
C(121) C(21) 1.5028(5) 1_555 1_555 yes
C(122) C(123) 1.4005(5) 1_555 1_555 yes
C(122) H(122) 1.0830(3) 1_555 1_555 yes
C(123) C(124) 1.3894(5) 1_555 1_555 yes
C(123) C(23) 1.5000(5) 1_555 1_555 yes
C(124) H(124) 1.0830(4) 1_555 1_555 yes
C(126) H(126) 1.0830(3) 1_555 1_555 yes
C(21) H(21A) 1.0590(5) 1_555 1_555 yes
C(21) H(21B) 1.0590(5) 1_555 1_555 yes
C(21) H(21C) 1.0590(5) 1_555 1_555 yes
C(23) H(23A) 1.0590(5) 1_555 1_555 yes
C(23) H(23B) 1.0590(6) 1_555 1_555 yes
C(23) H(23C) 1.0590(5) 1_555 1_555 yes
C(111) C(112) 1.4060(4) 1_555 1_555 yes
C(111) C(116) 1.4083(4) 1_555 1_555 yes
C(113) C(114) 1.4528(4) 1_555 1_555 yes
C(114) C(115) 1.3599(5) 1_555 1_555 yes
C(115) C(116) 1.5185(5) 1_555 1_555 yes

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C(115) O(5) H(5) 109.58(4) 1_555 1_555 1_555 yes
C(124) N(125) C(126) 122.98(3) 1_555 1_555 1_555 yes
C(124) N(125) H(125) 118.89(3) 1_555 1_555 1_555 yes
C(126) N(125) H(125) 118.12(3) 1_555 1_555 1_555 yes
C(122) C(121) C(126) 117.51(3) 1_555 1_555 1_555 yes
C(122) C(121) C(21) 122.89(4) 1_555 1_555 1_555 yes
C(126) C(121) C(21) 119.57(4) 1_555 1_555 1_555 yes
C(121) C(122) C(123) 121.47(3) 1_555 1_555 1_555 yes
C(121) C(122) H(122) 120.53(4) 1_555 1_555 1_555 yes
C(123) C(122) H(122) 117.92(3) 1_555 1_555 1_555 yes
C(122) C(123) C(124) 117.47(3) 1_555 1_555 1_555 yes
C(122) C(123) C(23) 122.53(4) 1_555 1_555 1_555 yes
C(124) C(123) C(23) 120.00(4) 1_555 1_555 1_555 yes
N(125) C(124) C(123) 120.26(3) 1_555 1_555 1_555 yes
N(125) C(124) H(124) 116.45(3) 1_555 1_555 1_555 yes
C(123) C(124) H(124) 123.26(3) 1_555 1_555 1_555 yes
N(125) C(126) C(121) 120.27(3) 1_555 1_555 1_555 yes
N(125) C(126) H(126) 115.94(3) 1_555 1_555 1_555 yes
C(121) C(126) H(126) 123.78(3) 1_555 1_555 1_555 yes
C(121) C(21) H(21A) 111.63(4) 1_555 1_555 1_555 yes
C(121) C(21) H(21B) 110.37(4) 1_555 1_555 1_555 yes
C(121) C(21) H(21C) 111.16(4) 1_555 1_555 1_555 yes
H(21A) C(21) H(21B) 106.83(4) 1_555 1_555 1_555 yes
H(21A) C(21) H(21C) 111.64(4) 1_555 1_555 1_555 yes
H(21B) C(21) H(21C) 104.91(5) 1_555 1_555 1_555 yes
C(123) C(23) H(23A) 111.31(4) 1_555 1_555 1_555 yes
C(123) C(23) H(23B) 110.89(4) 1_555 1_555 1_555 yes
C(123) C(23) H(23C) 109.94(4) 1_555 1_555 1_555 yes
H(23A) C(23) H(23B) 106.39(5) 1_555 1_555 1_555 yes
H(23A) C(23) H(23C) 112.80(4) 1_555 1_555 1_555 yes
H(23B) C(23) H(23C) 105.29(4) 1_555 1_555 1_555 yes
CL(1) C(111) C(112) 118.28(2) 1_555 1_555 1_555 yes
CL(1) C(111) C(116) 118.93(2) 1_555 1_555 1_555 yes
C(112) C(111) C(116) 122.65(3) 1_555 1_555 1_555 yes
O(2) C(112) C(111) 125.53(4) 1_555 1_555 1_555 yes
O(3) C(113) C(114) 123.18(4) 1_555 1_555 1_555 yes
CL(2) C(114) C(113) 118.17(2) 1_555 1_555 1_555 yes
CL(2) C(114) C(115) 121.68(3) 1_555 1_555 1_555 yes
C(113) C(114) C(115) 120.12(3) 1_555 1_555 1_555 yes
O(5) C(115) C(114) 122.22(4) 1_555 1_555 1_555 yes
O(5) C(115) C(116) 115.76(3) 1_555 1_555 1_555 yes
C(114) C(115) C(116) 122.00(3) 1_555 1_555 1_555 yes
O(6) C(116) C(111) 126.06(4) 1_555 1_555 1_555 yes
O(6) C(116) C(115) 115.75(3) 1_555 1_555 1_555 yes
C(111) C(116) C(115) 118.17(3) 1_555 1_555 1_555 yes

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
H(5) O(5) C(115) C(114) 179.55(6) 1_555 1_555 1_555 1_555 yes
H(5) O(5) C(115) C(116) 1.34(3) 1_555 1_555 1_555 1_555 yes
C(124) N(125) C(126) C(121) -1.10(4) 1_555 1_555 1_555 1_555 yes
C(126) N(125) C(124) C(123) 1.27(4) 1_555 1_555 1_555 1_555 yes
C(126) N(125) C(124) H(124) -176.71(6) 1_555 1_555 1_555 1_555 yes
C(124) N(125) C(126) H(126) -180.00(6) 1_555 1_555 1_555 1_555 yes
H(125) N(125) C(124) C(123) -179.38(6) 1_555 1_555 1_555 1_555 yes
H(125) N(125) C(124) H(124) 2.63(3) 1_555 1_555 1_555 1_555 yes
H(125) N(125) C(126) C(121) 179.56(6) 1_555 1_555 1_555 1_555 yes
H(125) N(125) C(126) H(126) 0.66(3) 1_555 1_555 1_555 1_555 yes
C(122) C(121) C(126) N(125) -0.60(4) 1_555 1_555 1_555 1_555 yes
C(126) C(121) C(122) C(123) 2.13(3) 1_555 1_555 1_555 1_555 yes
C(126) C(121) C(122) H(122) 178.62(6) 1_555 1_555 1_555 1_555 yes
C(122) C(121) C(126) H(126) 178.21(6) 1_555 1_555 1_555 1_555 yes
C(21) C(121) C(122) C(123) -176.22(6) 1_555 1_555 1_555 1_555 yes
C(21) C(121) C(122) H(122) 0.27(4) 1_555 1_555 1_555 1_555 yes
C(122) C(121) C(21) H(21A) -22.11(4) 1_555 1_555 1_555 1_555 yes
C(122) C(121) C(21) H(21B) 96.54(5) 1_555 1_555 1_555 1_555 yes
C(122) C(121) C(21) H(21C) -147.48(6) 1_555 1_555 1_555 1_555 yes
C(21) C(121) C(126) N(125) 177.80(6) 1_555 1_555 1_555 1_555 yes
C(21) C(121) C(126) H(126) -3.39(4) 1_555 1_555 1_555 1_555 yes
C(126) C(121) C(21) H(21A) 159.58(6) 1_555 1_555 1_555 1_555 yes
C(126) C(121) C(21) H(21B) -81.77(5) 1_555 1_555 1_555 1_555 yes
C(126) C(121) C(21) H(21C) 34.21(4) 1_555 1_555 1_555 1_555 yes
C(121) C(122) C(123) C(124) -1.96(4) 1_555 1_555 1_555 1_555 yes
C(121) C(122) C(123) C(23) 177.41(6) 1_555 1_555 1_555 1_555 yes
H(122) C(122) C(123) C(124) -178.54(5) 1_555 1_555 1_555 1_555 yes
H(122) C(122) C(123) C(23) 0.83(4) 1_555 1_555 1_555 1_555 yes
C(122) C(123) C(124) N(125) 0.26(3) 1_555 1_555 1_555 1_555 yes
C(122) C(123) C(124) H(124) 178.11(6) 1_555 1_555 1_555 1_555 yes
C(122) C(123) C(23) H(23A) -130.32(6) 1_555 1_555 1_555 1_555 yes
C(122) C(123) C(23) H(23B) 111.44(5) 1_555 1_555 1_555 1_555 yes
C(122) C(123) C(23) H(23C) -4.59(4) 1_555 1_555 1_555 1_555 yes
C(23) C(123) C(124) N(125) -179.12(6) 1_555 1_555 1_555 1_555 yes
C(23) C(123) C(124) H(124) -1.28(4) 1_555 1_555 1_555 1_555 yes
C(124) C(123) C(23) H(23A) 49.03(4) 1_555 1_555 1_555 1_555 yes
C(124) C(123) C(23) H(23B) -69.20(5) 1_555 1_555 1_555 1_555 yes
C(124) C(123) C(23) H(23C) 174.77(6) 1_555 1_555 1_555 1_555 yes
CL(1) C(111) C(112) O(2) -4.35(3) 1_555 1_555 1_555 1_555 yes
CL(1) C(111) C(116) O(6) 1.58(3) 1_555 1_555 1_555 1_555 yes
CL(1) C(111) C(116) C(115) -176.98(4) 1_555 1_555 1_555 1_555 yes
C(116) C(111) C(112) O(2) -179.98(6) 1_555 1_555 1_555 1_555 yes
C(112) C(111) C(116) O(6) 177.18(6) 1_555 1_555 1_555 1_555 yes
C(112) C(111) C(116) C(115) -1.39(3) 1_555 1_555 1_555 1_555 yes
O(3) C(113) C(114) CL(2) 1.85(4) 1_555 1_555 1_555 1_555 yes
O(3) C(113) C(114) C(115) -176.21(6) 1_555 1_555 1_555 1_555 yes
CL(2) C(114) C(115) O(5) -2.41(3) 1_555 1_555 1_555 1_555 yes
CL(2) C(114) C(115) C(116) 175.69(5) 1_555 1_555 1_555 1_555 yes
C(113) C(114) C(115) O(5) 175.59(5) 1_555 1_555 1_555 1_555 yes
C(113) C(114) C(115) C(116) -6.31(3) 1_555 1_555 1_555 1_555 yes
O(5) C(115) C(116) O(6) 4.82(4) 1_555 1_555 1_555 1_555 yes
O(5) C(115) C(116) C(111) -176.47(5) 1_555 1_555 1_555 1_555 yes
C(114) C(115) C(116) O(6) -173.40(5) 1_555 1_555 1_555 1_555 yes
C(114) C(115) C(116) C(111) 5.32(3) 1_555 1_555 1_555 1_555 yes
####################################################################### 
# 
# 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_3_shelx
_database_code_depnum_ccdc_archive 'CCDC 1478097'
_audit_update_record             
;
2016-05-04 deposited with the CCDC.
2016-06-13 downloaded from the CCDC.
;

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         
;
C6 Cl2 O4, 2(C7 H10 N), 4(H2 O) 
;
_chemical_formula_sum            'C20 H28 Cl2 N2 O8'
_chemical_formula_weight         495.34

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#
_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_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.9413(3)
_cell_length_b                   8.9010(4)
_cell_length_c                   9.0838(3)
_cell_angle_alpha                71.310(2)
_cell_angle_beta                 70.3580(10)
_cell_angle_gamma                76.061(2)
_cell_volume                     566.42(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    12071
_cell_measurement_theta_min      2.443
_cell_measurement_theta_max      51.277
_cell_measurement_wavelength     0.71073


#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            purple
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             260
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.336
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5187
_exptl_absorpt_correction_T_max  0.7496
_exptl_absorpt_process_details   'SADABS, Bruker(2001)'

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      -0.1331475
_diffrn_orient_matrix_UB_21      -0.15179E-2
_diffrn_orient_matrix_UB_31      0.219258E-1
_diffrn_orient_matrix_UB_12      0.319771E-1
_diffrn_orient_matrix_UB_22      0.531511E-1
_diffrn_orient_matrix_UB_32      0.1023231
_diffrn_orient_matrix_UB_13      0.201288E-1
_diffrn_orient_matrix_UB_23      0.822603E-1
_diffrn_orient_matrix_UB_33      -0.868276E-1
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_reflns_av_R_equivalents  0.0837
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_number            12074
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.44
_diffrn_reflns_theta_max         51.28
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.96
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.96
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.96
_reflns_Friedel_coverage         0
_reflns_number_total             12071
_reflns_number_gt                10236
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
 Scaled and merged with Sortav
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0577P)²+0.0089P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_number_reflns         12071
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.0289
_refine_ls_wR_factor_ref         0.0903
_refine_ls_wR_factor_gt          0.0872
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.6
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.058

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.76235(2) 0.45580(2) 0.30214(2) 0.02054(2) Uani 1 1 d . . . . .
O2 O 1.03649(4) 0.21525(3) 0.43789(3) 0.01790(4) Uani 1 1 d . . . . .
O3 O 1.25160(4) 0.25742(3) 0.58894(4) 0.01908(4) Uani 1 1 d . . . . .
O111 O 1.18422(4) -0.06939(3) 0.66261(4) 0.01958(4) Uani 1 1 d . . . . .
O121 O 1.52947(4) -0.16631(4) 0.69052(4) 0.02050(4) Uani 1 1 d . . . . .
N125 N 1.65482(4) 0.04067(4) 0.77664(3) 0.01761(4) Uani 1 1 d . . . . .
C121 C 1.63704(4) 0.31397(4) 0.75837(4) 0.01841(4) Uani 1 1 d . . . . .
C122 C 1.71941(4) 0.27287(4) 0.88239(4) 0.01665(4) Uani 1 1 d . . . . .
C123 C 1.77003(4) 0.11065(4) 0.94959(4) 0.01705(4) Uani 1 1 d . . . . .
C124 C 1.73801(4) -0.00604(4) 0.89491(4) 0.01620(4) Uani 1 1 d . . . . .
C126 C 1.60455(5) 0.19547(5) 0.70847(4) 0.01942(5) Uani 1 1 d . . . . .
C22 C 1.74635(6) 0.39947(6) 0.94527(5) 0.02471(6) Uani 1 1 d . . . . .
C24 C 1.78866(6) -0.18100(5) 0.96023(5) 0.02366(6) Uani 1 1 d . . . . .
C111 C 0.89588(4) 0.48235(3) 0.40626(3) 0.01365(4) Uani 1 1 d . . . . .
C112 C 1.01704(4) 0.35021(3) 0.45976(3) 0.01276(3) Uani 1 1 d . . . . .
C113 C 1.13447(4) 0.37218(3) 0.55442(3) 0.01299(3) Uani 1 1 d . . . . .
H121 H 1.6034(14) 0.4207(12) 0.7078(13) 0.035(2) Uiso 1 1 d . . . . .
H123 H 1.8218(13) 0.0836(11) 1.0337(11) 0.027(2) Uiso 1 1 d . . . . .
H125 H 1.6260(15) -0.0364(14) 0.7413(14) 0.046(3) Uiso 1 1 d . . . . .
H126 H 1.5432(14) 0.2150(12) 0.6293(12) 0.030(2) Uiso 1 1 d . . . . .
H22A H 1.6701(16) 0.3926(13) 1.0489(15) 0.051(3) Uiso 1 1 d . . . . .
H22B H 1.8644(16) 0.3868(13) 0.9406(15) 0.050(3) Uiso 1 1 d . . . . .
H22C H 1.7113(17) 0.5162(15) 0.8714(16) 0.052(3) Uiso 1 1 d . . . . .
H24A H 1.7024(13) -0.2432(12) 0.9690(12) 0.030(2) Uiso 1 1 d . . . . .
H24B H 1.8973(13) -0.2165(13) 0.8874(12) 0.034(2) Uiso 1 1 d . . . . .
H24C H 1.7885(14) -0.2046(12) 1.0641(13) 0.038(3) Uiso 1 1 d . . . . .
H1A H 1.1618(15) 0.0309(13) 0.6121(13) 0.042(3) Uiso 1 1 d . . . . .
H1B H 1.1329(15) -0.1189(13) 0.6220(14) 0.042(3) Uiso 1 1 d . . . . .
H2A H 1.4229(14) -0.1391(12) 0.6785(13) 0.038(3) Uiso 1 1 d . . . . .
H2B H 1.6011(13) -0.1861(11) 0.6077(12) 0.030(2) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   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 C111 1.7359(3) . ?
O2 C112 1.2448(3) . ?
O3 C113 1.2410(3) . ?
O111 H1A 0.869(11) . ?
O111 H1B 0.888(11) . ?
O121 H2A 0.856(11) . ?
O121 H2B 0.819(10) . ?
N125 C126 1.3400(5) . ?
N125 C124 1.3499(4) . ?
N125 H125 0.945(12) . ?
C121 C126 1.3787(5) . ?
C121 C122 1.3953(5) . ?
C121 H121 0.930(10) . ?
C122 C123 1.3927(5) . ?
C122 C22 1.5009(5) . ?
C123 C124 1.3903(5) . ?
C123 H123 0.926(10) . ?
C124 C24 1.4851(5) . ?
C126 H126 0.949(10) . ?
C22 H22A 0.924(12) . ?
C22 H22B 0.905(12) . ?
C22 H22C 1.070(13) . ?
C24 H24A 0.949(10) . ?
C24 H24B 0.949(10) . ?
C24 H24C 0.898(11) . ?
C111 C112 1.3958(4) . ?
C111 C113 1.3965(4) 2_766 ?
C112 C113 1.5433(4) . ?
C113 C111 1.3965(4) 2_766 ?

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
H1A O111 H1B 103.2(10) . . ?
H2A O121 H2B 109.3(10) . . ?
C126 N125 C124 122.33(3) . . ?
C126 N125 H125 117.3(7) . . ?
C124 N125 H125 120.4(7) . . ?
C126 C121 C122 120.01(3) . . ?
C126 C121 H121 118.8(7) . . ?
C122 C121 H121 121.2(7) . . ?
C123 C122 C121 117.91(3) . . ?
C123 C122 C22 121.13(3) . . ?
C121 C122 C22 120.92(3) . . ?
C124 C123 C122 120.73(3) . . ?
C124 C123 H123 121.5(6) . . ?
C122 C123 H123 117.7(6) . . ?
N125 C124 C123 118.77(3) . . ?
N125 C124 C24 117.46(3) . . ?
C123 C124 C24 123.77(3) . . ?
N125 C126 C121 120.23(3) . . ?
N125 C126 H126 115.5(6) . . ?
C121 C126 H126 124.2(6) . . ?
C122 C22 H22A 109.0(7) . . ?
C122 C22 H22B 108.8(7) . . ?
H22A C22 H22B 112.9(11) . . ?
C122 C22 H22C 110.1(7) . . ?
H22A C22 H22C 107.6(9) . . ?
H22B C22 H22C 108.3(10) . . ?
C124 C24 H24A 113.7(6) . . ?
C124 C24 H24B 108.4(6) . . ?
H24A C24 H24B 105.9(8) . . ?
C124 C24 H24C 111.2(7) . . ?
H24A C24 H24C 101.0(9) . . ?
H24B C24 H24C 116.5(9) . . ?
C112 C111 C113 123.28(2) . 2_766 ?
C112 C111 Cl1 117.42(2) . . ?
C113 C111 Cl1 119.01(2) 2_766 . ?
O2 C112 C111 124.80(3) . . ?
O2 C112 C113 117.45(2) . . ?
C111 C112 C113 117.75(2) . . ?
O3 C113 C111 124.67(3) . 2_766 ?
O3 C113 C112 116.58(2) . . ?
C111 C113 C112 118.74(2) 2_766 . ?

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
C126 C121 C122 C123 1.41(5) . . . . ?
C126 C121 C122 C22 -176.42(3) . . . . ?
C121 C122 C123 C124 -0.40(5) . . . . ?
C22 C122 C123 C124 177.42(3) . . . . ?
C126 N125 C124 C123 1.04(5) . . . . ?
C126 N125 C124 C24 -179.51(3) . . . . ?
C122 C123 C124 N125 -0.80(5) . . . . ?
C122 C123 C124 C24 179.79(3) . . . . ?
C124 N125 C126 C121 -0.03(5) . . . . ?
C122 C121 C126 N125 -1.23(5) . . . . ?
C113 C111 C112 O2 173.91(3) 2_766 . . . ?
Cl1 C111 C112 O2 0.19(4) . . . . ?
C113 C111 C112 C113 -5.48(5) 2_766 . . . ?
Cl1 C111 C112 C113 -179.20(2) . . . . ?
O2 C112 C113 O3 6.40(4) . . . . ?
C111 C112 C113 O3 -174.16(3) . . . . ?
O2 C112 C113 C111 -174.21(3) . . . 2_766 ?
C111 C112 C113 C111 5.23(4) . . . 2_766 ?

####################################################################### 
# 
# 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_4_shelx
_database_code_depnum_ccdc_archive 'CCDC 1478098'
_audit_update_record             
;
2016-05-04 deposited with the CCDC.
2016-06-13 downloaded from the CCDC.
;

_chemical_name_systematic        
;                                                          
 ?                                                         
;
_chemical_formula_moiety         
;                                                          
C6 Cl2 O4, 2(C7 H10 N), 2(H2 O)                                      
;
_chemical_formula_sum            'C20 H24 Cl2 N2 O6'
_chemical_formula_weight         459.33

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.036(2)
_cell_length_b                   7.6591(17)
_cell_length_c                   13.948(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.620(14)
_cell_angle_gamma                90
_cell_volume                     1057.1(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2162
_cell_measurement_theta_min      2.1
_cell_measurement_theta_max      26.5
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#
_exptl_crystal_description       block
_exptl_crystal_colour            'dark red'
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.10
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             480
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.347
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9169
_exptl_absorpt_correction_T_max  0.9659
_exptl_absorpt_process_details   'SADABS, Bruker(2001)'


#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_reflns_av_R_equivalents  0.0616
_diffrn_reflns_number            9350
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.058
_diffrn_reflns_theta_max         26.474
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.992
_reflns_number_total             2162
_reflns_number_gt                1576
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0463P)²+0.0223P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2162
_refine_ls_number_parameters     184
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0429
_refine_ls_wR_factor_ref         0.0991
_refine_ls_wR_factor_gt          0.0909
_refine_ls_goodness_of_fit_ref   1.04
_refine_ls_restrained_S_all      1.04
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.065

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 1.00408(6) -0.14013(7) 0.28608(4) 0.01976(18) Uani 1 d . .
O2 O 1.22351(15) 0.04717(19) 0.41886(11) 0.0193(4) Uani 1 d . .
O3 O 1.22001(15) 0.1593(2) 0.59733(11) 0.0204(4) Uani 1 d . .
O11 O 1.30185(18) 0.0722(2) 0.23511(14) 0.0240(4) Uani 1 d . .
N125 N 1.4523(2) 0.2085(2) 0.50150(14) 0.0187(4) Uani 1 d . .
C121 C 1.6393(2) 0.2997(3) 0.43417(17) 0.0208(5) Uani 1 d . .
C122 C 1.6969(2) 0.3743(3) 0.52211(17) 0.0173(5) Uani 1 d . .
C123 C 1.6271(2) 0.3643(3) 0.60130(16) 0.0171(5) Uani 1 d . .
C124 C 1.5044(2) 0.2791(3) 0.58746(18) 0.0194(5) Uani 1 d . .
C126 C 1.5169(2) 0.2169(3) 0.42505(18) 0.0204(5) Uani 1 d . .
C22 C 1.8298(3) 0.4674(4) 0.5322(2) 0.0253(6) Uani 1 d . .
C23 C 1.6809(3) 0.4421(4) 0.69788(19) 0.0253(6) Uani 1 d . .
C111 C 1.0013(2) -0.0605(3) 0.40239(16) 0.0165(5) Uani 1 d . .
C112 C 1.1165(2) 0.0203(3) 0.45196(16) 0.0161(5) Uani 1 d . .
C113 C 1.1155(2) 0.0863(3) 0.55620(16) 0.0159(5) Uani 1 d . .
H121 H 1.690(2) 0.308(3) 0.3778(17) 0.025(6) Uiso 1 d . .
H124 H 1.451(2) 0.263(3) 0.6408(17) 0.029(7) Uiso 1 d . .
H125 H 1.362(3) 0.155(3) 0.4892(19) 0.046(8) Uiso 1 d . .
H126 H 1.471(2) 0.166(3) 0.3665(18) 0.025(7) Uiso 1 d . .
H22A H 1.862(2) 0.464(3) 0.4714(19) 0.031(7) Uiso 1 d . .
H22B H 1.894(3) 0.414(3) 0.5809(18) 0.027(7) Uiso 1 d . .
H22C H 1.821(3) 0.585(4) 0.544(2) 0.049(9) Uiso 1 d . .
H23A H 1.708(2) 0.568(3) 0.6904(16) 0.026(7) Uiso 1 d . .
H23B H 1.759(3) 0.383(3) 0.732(2) 0.041(8) Uiso 1 d . .
H23C H 1.617(3) 0.440(3) 0.745(2) 0.047(8) Uiso 1 d . .
H11A H 1.249(3) 0.155(5) 0.203(3) 0.073(12) Uiso 1 d . .
H11B H 1.267(3) 0.052(4) 0.279(2) 0.038(9) Uiso 1 d . .



#----------------------------------------------------------------------------#
#                   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 C111 1.738(2) . ?
O2 C112 1.255(2) . ?
O3 C113 1.241(3) . ?
O11 H11A 0.90(4) . ?
O11 H11B 0.77(3) . ?
N125 C126 1.339(3) . ?
N125 C124 1.339(3) . ?
N125 H125 0.98(3) . ?
C121 C126 1.369(3) . ?
C121 C122 1.389(3) . ?
C121 H121 1.01(2) . ?
C122 C123 1.406(3) . ?
C122 C22 1.498(3) . ?
C123 C124 1.378(3) . ?
C123 C23 1.490(3) . ?
C124 H124 0.99(2) . ?
C126 H126 0.95(2) . ?
C22 H22A 0.96(2) . ?
C22 H22B 0.95(3) . ?
C22 H22C 0.92(3) . ?
C23 H23A 1.01(2) . ?
C23 H23B 0.96(3) . ?
C23 H23C 1.00(3) . ?
C111 C112 1.390(3) . ?
C111 C113 1.404(3) 3_756 ?
C112 C113 1.541(3) . ?
C113 C111 1.404(3) 3_756 ?

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
H11A O11 H11B 104(3) . . ?
C126 N125 C124 121.6(2) . . ?
C126 N125 H125 115.8(16) . . ?
C124 N125 H125 122.4(16) . . ?
C126 C121 C122 120.5(2) . . ?
C126 C121 H121 121.3(14) . . ?
C122 C121 H121 118.3(14) . . ?
C121 C122 C123 118.9(2) . . ?
C121 C122 C22 120.8(2) . . ?
C123 C122 C22 120.3(2) . . ?
C124 C123 C122 117.8(2) . . ?
C124 C123 C23 119.8(2) . . ?
C122 C123 C23 122.4(2) . . ?
N125 C124 C123 121.5(2) . . ?
N125 C124 H124 116.1(14) . . ?
C123 C124 H124 122.3(14) . . ?
N125 C126 C121 119.7(2) . . ?
N125 C126 H126 115.7(14) . . ?
C121 C126 H126 124.6(15) . . ?
C122 C22 H22A 109.4(15) . . ?
C122 C22 H22B 110.6(15) . . ?
H22A C22 H22B 109(2) . . ?
C122 C22 H22C 111.5(18) . . ?
H22A C22 H22C 104(2) . . ?
H22B C22 H22C 112(2) . . ?
C123 C23 H23A 110.5(13) . . ?
C123 C23 H23B 113.8(16) . . ?
H23A C23 H23B 107(2) . . ?
C123 C23 H23C 114.6(16) . . ?
H23A C23 H23C 107(2) . . ?
H23B C23 H23C 103(2) . . ?
C112 C111 C113 122.7(2) . 3_756 ?
C112 C111 Cl1 118.62(16) . . ?
C113 C111 Cl1 118.65(17) 3_756 . ?
O2 C112 C111 125.6(2) . . ?
O2 C112 C113 115.75(19) . . ?
C111 C112 C113 118.65(18) . . ?
O3 C113 C111 124.9(2) . 3_756 ?
O3 C113 C112 116.45(18) . . ?
C111 C113 C112 118.7(2) 3_756 . ?

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
C126 C121 C122 C123 -0.4(3) . . . . ?
C126 C121 C122 C22 -179.1(2) . . . . ?
C121 C122 C123 C124 0.5(3) . . . . ?
C22 C122 C123 C124 179.2(2) . . . . ?
C121 C122 C123 C23 -179.4(2) . . . . ?
C22 C122 C123 C23 -0.7(3) . . . . ?
C126 N125 C124 C123 0.2(3) . . . . ?
C122 C123 C124 N125 -0.4(3) . . . . ?
C23 C123 C124 N125 179.5(2) . . . . ?
C124 N125 C126 C121 -0.2(3) . . . . ?
C122 C121 C126 N125 0.3(4) . . . . ?
C113 C111 C112 O2 -179.9(2) 3_756 . . . ?
Cl1 C111 C112 O2 2.5(3) . . . . ?
C113 C111 C112 C113 -0.7(4) 3_756 . . . ?
Cl1 C111 C112 C113 -178.28(15) . . . . ?
O2 C112 C113 O3 0.0(3) . . . . ?
C111 C112 C113 O3 -179.27(19) . . . . ?
O2 C112 C113 C111 179.95(19) . . . 3_756 ?
C111 C112 C113 C111 0.7(3) . . . 3_756 ?

####################################################################### 
# 
# 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_5_shelx
_database_code_depnum_ccdc_archive 'CCDC 1478099'
_audit_update_record             
;
2016-05-04 deposited with the CCDC.
2016-06-13 downloaded from the CCDC.
;

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         
;
C6 Cl2 O4, 2(C7 H10 N), 3(H2 O) 
;
_chemical_formula_sum            'C20 H26 Cl2 N2 O7'
_chemical_formula_weight         477.33

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14


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

_cell_length_a                   10.6104(4)
_cell_length_b                   17.7659(7)
_cell_length_c                   12.3211(5)
_cell_angle_alpha                90
_cell_angle_beta                 108.6810(10)
_cell_angle_gamma                90
_cell_volume                     2200.21(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    23247
_cell_measurement_theta_min      2.088
_cell_measurement_theta_max      50.379
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            purple
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.19
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1000
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.34
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.0241
_exptl_absorpt_correction_T_max  0.7493
_exptl_absorpt_process_details   'SADABS, Bruker(2001)'

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      0.593768E-1
_diffrn_orient_matrix_UB_21      0.560025E-1
_diffrn_orient_matrix_UB_31      -0.568867E-1
_diffrn_orient_matrix_UB_12      -0.340404E-1
_diffrn_orient_matrix_UB_22      -0.85987E-2
_diffrn_orient_matrix_UB_32      -0.439955E-1
_diffrn_orient_matrix_UB_13      -0.264207E-1
_diffrn_orient_matrix_UB_23      0.813732E-1
_diffrn_orient_matrix_UB_33      0.45384E-2
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_reflns_av_R_equivalents  0.0837
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_number            23249
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.09
_diffrn_reflns_theta_max         50.38
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_reflns_Friedel_coverage         0
_reflns_number_total             23247
_reflns_number_gt                18653
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#


_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0604P)²+0.0212P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         23247
_refine_ls_number_parameters     373
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0334
_refine_ls_wR_factor_ref         0.1008
_refine_ls_wR_factor_gt          0.0962
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.592
_refine_diff_density_min         -0.591
_refine_diff_density_rms         0.069

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.88679(2) 0.44971(2) 0.32009(2) 0.01897(2) Uani 1 1 d . . . . .
Cl2 Cl 0.88587(2) 0.09161(2) 0.33223(2) 0.01806(2) Uani 1 1 d . . . . .
O2 O 1.05890(3) 0.34334(2) 0.24090(2) 0.01501(3) Uani 1 1 d . . . . .
O3 O 1.05866(3) 0.19398(2) 0.24611(2) 0.01486(3) Uani 1 1 d . . . . .
O4 O 0.71646(3) 0.19863(2) 0.41456(2) 0.01539(4) Uani 1 1 d . . . . .
O5 O 0.72044(3) 0.34844(2) 0.41163(3) 0.01613(4) Uani 1 1 d . . . . .
O11 O 1.13264(4) 0.04432(2) 0.18682(4) 0.02578(6) Uani 1 1 d . . . . .
O12 O 1.38987(3) -0.01185(2) 0.32782(3) 0.01976(4) Uani 1 1 d . . . . .
O13 O 0.62749(5) 0.05899(3) 0.46580(4) 0.03000(8) Uani 1 1 d . . . . .
N125 N 1.26615(3) 0.26954(2) 0.19437(3) 0.01613(4) Uani 1 1 d . . . . .
N225 N 0.51235(3) 0.29298(2) 0.46401(3) 0.01869(5) Uani 1 1 d . . . . .
C121 C 1.44686(3) 0.33834(2) 0.16986(3) 0.01438(4) Uani 1 1 d . . . . .
C122 C 1.50506(3) 0.26947(2) 0.15845(3) 0.01404(4) Uani 1 1 d . . . . .
C123 C 1.44266(3) 0.20066(2) 0.16324(3) 0.01407(4) Uani 1 1 d . . . . .
C124 C 1.31975(3) 0.20308(2) 0.18085(3) 0.01601(4) Uani 1 1 d . . . . .
C126 C 1.32478(3) 0.33582(2) 0.18909(3) 0.01599(4) Uani 1 1 d . . . . .
C221 C 0.33267(3) 0.36105(2) 0.49103(3) 0.01660(5) Uani 1 1 d . . . . .
C222 C 0.27299(3) 0.29169(2) 0.49861(3) 0.01619(4) Uani 1 1 d . . . . .
C223 C 0.33398(3) 0.22305(2) 0.49094(3) 0.01646(5) Uani 1 1 d . . . . .
C224 C 0.45711(4) 0.22616(2) 0.47338(3) 0.01847(5) Uani 1 1 d . . . . .
C226 C 0.45536(4) 0.35917(2) 0.47293(3) 0.01843(5) Uani 1 1 d . . . . .
C21 C 1.51072(5) 0.41282(2) 0.16259(4) 0.02227(6) Uani 1 1 d . . . . .
C23 C 1.50314(5) 0.12622(2) 0.15000(4) 0.02058(6) Uani 1 1 d . . . . .
C31 C 0.26883(5) 0.43498(3) 0.50198(4) 0.02356(6) Uani 1 1 d . . . . .
C33 C 0.27215(5) 0.14814(3) 0.50042(4) 0.02251(6) Uani 1 1 d . . . . .
H33A H 0.304 0.1108 0.4592 0.034 Uiso 1 1 calc R U . . .
H33B H 0.1771 0.1519 0.4686 0.034 Uiso 1 1 calc R U . . .
H33C H 0.2959 0.1339 0.5796 0.034 Uiso 1 1 calc R U . . .
C111 C 0.88832(3) 0.35205(2) 0.32493(3) 0.01330(4) Uani 1 1 d . . . . .
C112 C 0.97736(3) 0.31311(2) 0.28226(3) 0.01180(3) Uani 1 1 d . . . . .
C113 C 0.97722(3) 0.22612(2) 0.28497(3) 0.01171(3) Uani 1 1 d . . . . .
C114 C 0.88749(3) 0.18941(2) 0.33039(3) 0.01311(4) Uani 1 1 d . . . . .
C115 C 0.79846(3) 0.22836(2) 0.37401(3) 0.01188(4) Uani 1 1 d . . . . .
C116 C 0.79958(3) 0.31538(2) 0.37181(3) 0.01216(4) Uani 1 1 d . . . . .
H122 H 1.5935(11) 0.2690(6) 0.1463(10) 0.028(3) Uiso 1 1 d . . . . .
H124 H 1.2702(11) 0.1588(6) 0.1833(9) 0.033(3) Uiso 1 1 d . . . . .
H125 H 1.1837(13) 0.2715(7) 0.2059(11) 0.042(3) Uiso 1 1 d . . . . .
H126 H 1.2824(10) 0.3787(6) 0.2011(9) 0.031(3) Uiso 1 1 d . . . . .
H222 H 0.1832(10) 0.2920(6) 0.5080(9) 0.028(2) Uiso 1 1 d . . . . .
H224 H 0.5045(11) 0.1830(7) 0.4620(10) 0.037(3) Uiso 1 1 d . . . . .
H225 H 0.5958(13) 0.2935(7) 0.4497(11) 0.043(3) Uiso 1 1 d . . . . .
H226 H 0.5015(11) 0.4051(6) 0.4660(9) 0.032(3) Uiso 1 1 d . . . . .
H21A H 1.4968(17) 0.4491(10) 0.2105(16) 0.084(6) Uiso 1 1 d . . . . .
H21B H 1.4781(15) 0.4315(9) 0.0912(15) 0.069(5) Uiso 1 1 d . . . . .
H21C H 1.598(2) 0.4084(13) 0.1868(17) 0.111(7) Uiso 1 1 d . . . . .
H23A H 1.4675(13) 0.0832(8) 0.1867(12) 0.059(4) Uiso 1 1 d . . . . .
H23B H 1.4839(12) 0.1157(7) 0.0716(10) 0.040(3) Uiso 1 1 d . . . . .
H23C H 1.5960(13) 0.1269(9) 0.1925(12) 0.060(4) Uiso 1 1 d . . . . .
H31A H 0.2993(12) 0.4760(7) 0.4672(11) 0.043(3) Uiso 1 1 d . . . . .
H31B H 0.1690(13) 0.4320(7) 0.4622(11) 0.046(3) Uiso 1 1 d . . . . .
H31C H 0.2832(12) 0.4482(7) 0.5840(11) 0.044(3) Uiso 1 1 d . . . . .
H11A H 1.1068(13) 0.0817(8) 0.2233(12) 0.051(4) Uiso 1 1 d . . . . .
H11B H 1.2085(12) 0.0293(7) 0.2334(10) 0.040(3) Uiso 1 1 d . . . . .
H12A H 1.4130(12) -0.0519(7) 0.2981(12) 0.043(3) Uiso 1 1 d . . . . .
H12B H 1.3869(15) -0.0276(9) 0.3918(14) 0.066(4) Uiso 1 1 d . . . . .
H13A H 0.6600(14) 0.0952(8) 0.4381(12) 0.057(4) Uiso 1 1 d . . . . .
H13B H 0.5728(11) 0.0474(6) 0.4178(10) 0.030(3) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   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 C111 1.7358(3) . ?
Cl2 C114 1.7377(3) . ?
O2 C112 1.2566(4) . ?
O3 C113 1.2518(4) . ?
O4 C115 1.2506(4) . ?
O5 C116 1.2470(4) . ?
O11 H11A 0.893(14) . ?
O11 H11B 0.868(13) . ?
O12 H12A 0.871(13) . ?
O12 H12B 0.846(16) . ?
O13 H13A 0.851(15) . ?
O13 H13B 0.713(12) . ?
N125 C126 1.3431(5) . ?
N125 C124 1.3438(5) . ?
N125 H125 0.931(13) . ?
N225 C226 1.3429(6) . ?
N225 C224 1.3451(6) . ?
N225 H225 0.957(13) . ?
C121 C126 1.3902(5) . ?
C121 C122 1.3978(4) . ?
C121 C21 1.5023(5) . ?
C122 C123 1.4006(5) . ?
C122 H122 0.996(11) . ?
C123 C124 1.3895(5) . ?
C123 C23 1.5014(5) . ?
C124 H124 0.953(11) . ?
C126 H126 0.921(11) . ?
C221 C226 1.3898(5) . ?
C221 C222 1.4021(5) . ?
C221 C31 1.5036(6) . ?
C222 C223 1.3979(5) . ?
C222 H222 0.996(10) . ?
C223 C224 1.3921(5) . ?
C223 C33 1.5046(6) . ?
C224 H224 0.952(11) . ?
C226 H226 0.969(11) . ?
C21 H21A 0.917(19) . ?
C21 H21B 0.899(17) . ?
C21 H21C 0.89(2) . ?
C23 H23A 1.021(14) . ?
C23 H23B 0.939(12) . ?
C23 H23C 0.957(13) . ?
C31 H31A 0.953(13) . ?
C31 H31B 1.016(13) . ?
C31 H31C 1.000(13) . ?
C33 H33A 0.96 . ?
C33 H33B 0.96 . ?
C33 H33C 0.96 . ?
C111 C112 1.4021(4) . ?
C111 C116 1.4118(4) . ?
C112 C113 1.5459(4) . ?
C113 C114 1.4094(4) . ?
C114 C115 1.4089(4) . ?
C115 C116 1.5463(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
H11A O11 H11B 105.3(12) . . ?
H12A O12 H12B 102.8(13) . . ?
H13A O13 H13B 102.2(12) . . ?
C126 N125 C124 122.91(3) . . ?
C126 N125 H125 116.5(7) . . ?
C124 N125 H125 120.5(7) . . ?
C226 N225 C224 123.08(3) . . ?
C226 N225 H225 118.3(8) . . ?
C224 N225 H225 118.6(8) . . ?
C126 C121 C122 117.05(3) . . ?
C126 C121 C21 120.08(3) . . ?
C122 C121 C21 122.87(3) . . ?
C121 C122 C123 121.99(3) . . ?
C121 C122 H122 119.3(6) . . ?
C123 C122 H122 118.7(6) . . ?
C124 C123 C122 117.35(3) . . ?
C124 C123 C23 119.97(3) . . ?
C122 C123 C23 122.68(3) . . ?
N125 C124 C123 120.15(3) . . ?
N125 C124 H124 117.5(7) . . ?
C123 C124 H124 122.3(7) . . ?
N125 C126 C121 120.52(3) . . ?
N125 C126 H126 117.4(7) . . ?
C121 C126 H126 122.0(7) . . ?
C226 C221 C222 117.12(3) . . ?
C226 C221 C31 120.49(4) . . ?
C222 C221 C31 122.39(3) . . ?
C223 C222 C221 122.24(3) . . ?
C223 C222 H222 119.5(6) . . ?
C221 C222 H222 118.2(6) . . ?
C224 C223 C222 116.97(3) . . ?
C224 C223 C33 120.10(4) . . ?
C222 C223 C33 122.93(3) . . ?
N225 C224 C223 120.33(4) . . ?
N225 C224 H224 115.7(7) . . ?
C223 C224 H224 123.9(7) . . ?
N225 C226 C221 120.24(4) . . ?
N225 C226 H226 118.4(6) . . ?
C221 C226 H226 121.3(6) . . ?
C121 C21 H21A 114.3(11) . . ?
C121 C21 H21B 110.1(10) . . ?
H21A C21 H21B 106.2(14) . . ?
C121 C21 H21C 110.4(15) . . ?
H21A C21 H21C 102.3(16) . . ?
H21B C21 H21C 113.4(15) . . ?
C123 C23 H23A 112.3(8) . . ?
C123 C23 H23B 109.1(8) . . ?
H23A C23 H23B 108.5(11) . . ?
C123 C23 H23C 109.4(9) . . ?
H23A C23 H23C 103.2(11) . . ?
H23B C23 H23C 114.3(11) . . ?
C221 C31 H31A 113.6(7) . . ?
C221 C31 H31B 110.0(7) . . ?
H31A C31 H31B 105.9(10) . . ?
C221 C31 H31C 111.6(7) . . ?
H31A C31 H31C 108.1(10) . . ?
H31B C31 H31C 107.3(10) . . ?
C223 C33 H33A 109.5 . . ?
C223 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C223 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C112 C111 C116 122.92(3) . . ?
C112 C111 Cl1 118.71(2) . . ?
C116 C111 Cl1 118.37(2) . . ?
O2 C112 C111 125.12(3) . . ?
O2 C112 C113 116.20(2) . . ?
C111 C112 C113 118.67(2) . . ?
O3 C113 C114 125.29(3) . . ?
O3 C113 C112 116.24(2) . . ?
C114 C113 C112 118.46(2) . . ?
C115 C114 C113 123.02(3) . . ?
C115 C114 Cl2 118.39(2) . . ?
C113 C114 Cl2 118.59(2) . . ?
O4 C115 C114 125.61(3) . . ?
O4 C115 C116 116.07(3) . . ?
C114 C115 C116 118.33(2) . . ?
O5 C116 C111 124.40(3) . . ?
O5 C116 C115 117.02(2) . . ?
C111 C116 C115 118.58(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
C126 C121 C122 C123 1.52(5) . . . . ?
C21 C121 C122 C123 -178.71(4) . . . . ?
C121 C122 C123 C124 -0.51(5) . . . . ?
C121 C122 C123 C23 179.38(3) . . . . ?
C126 N125 C124 C123 1.61(5) . . . . ?
C122 C123 C124 N125 -1.05(5) . . . . ?
C23 C123 C124 N125 179.05(3) . . . . ?
C124 N125 C126 C121 -0.53(5) . . . . ?
C122 C121 C126 N125 -1.01(5) . . . . ?
C21 C121 C126 N125 179.21(4) . . . . ?
C226 C221 C222 C223 1.32(5) . . . . ?
C31 C221 C222 C223 -178.54(4) . . . . ?
C221 C222 C223 C224 -1.02(5) . . . . ?
C221 C222 C223 C33 179.19(3) . . . . ?
C226 N225 C224 C223 1.30(6) . . . . ?
C222 C223 C224 N225 -0.28(5) . . . . ?
C33 C223 C224 N225 179.51(4) . . . . ?
C224 N225 C226 C221 -0.98(6) . . . . ?
C222 C221 C226 N225 -0.33(5) . . . . ?
C31 C221 C226 N225 179.53(4) . . . . ?
C116 C111 C112 O2 -179.24(3) . . . . ?
Cl1 C111 C112 O2 0.75(5) . . . . ?
C116 C111 C112 C113 0.89(5) . . . . ?
Cl1 C111 C112 C113 -179.11(2) . . . . ?
O2 C112 C113 O3 0.25(4) . . . . ?
C111 C112 C113 O3 -179.87(3) . . . . ?
O2 C112 C113 C114 -179.92(3) . . . . ?
C111 C112 C113 C114 -0.04(4) . . . . ?
O3 C113 C114 C115 179.45(3) . . . . ?
C112 C113 C114 C115 -0.36(4) . . . . ?
O3 C113 C114 Cl2 -0.84(5) . . . . ?
C112 C113 C114 Cl2 179.35(2) . . . . ?
C113 C114 C115 O4 179.56(3) . . . . ?
Cl2 C114 C115 O4 -0.15(5) . . . . ?
C113 C114 C115 C116 -0.02(4) . . . . ?
Cl2 C114 C115 C116 -179.73(2) . . . . ?
C112 C111 C116 O5 179.11(3) . . . . ?
Cl1 C111 C116 O5 -0.89(5) . . . . ?
C112 C111 C116 C115 -1.27(5) . . . . ?
Cl1 C111 C116 C115 178.73(2) . . . . ?
O4 C115 C116 O5 0.85(4) . . . . ?
C114 C115 C116 O5 -179.53(3) . . . . ?
O4 C115 C116 C111 -178.79(3) . . . . ?
C114 C115 C116 C111 0.83(4) . . . . ?

####################################################################### 
# 
# 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_6_shelx
_database_code_depnum_ccdc_archive 'CCDC 1478100'
_audit_update_record             
;
2016-05-04 deposited with the CCDC.
2016-06-13 downloaded from the CCDC.
;

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         
;
C6 Cl2 O4, 0.5(C6 H4 Cl2 O4), C7 H10 N
;
_chemical_formula_sum            'C16 H12 Cl3 N O6'
_chemical_formula_weight         420.62

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#
_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_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.0154(3)
_cell_length_b                   9.3997(3)
_cell_length_c                   11.8524(5)
_cell_angle_alpha                71.632(2)
_cell_angle_beta                 88.044(2)
_cell_angle_gamma                86.436(2)
_cell_volume                     845.75(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4974
_cell_measurement_theta_min      1.811
_cell_measurement_theta_max      30.23
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            purple
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_crystal_density_diffrn    1.652
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             428
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.577
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5090
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS, Bruker(2001)'

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      0.0082621
_diffrn_orient_matrix_UB_21      0.1197947
_diffrn_orient_matrix_UB_31      -0.0347857
_diffrn_orient_matrix_UB_12      -0.0382719
_diffrn_orient_matrix_UB_22      -0.0328348
_diffrn_orient_matrix_UB_32      -0.1002994
_diffrn_orient_matrix_UB_13      -0.0698410
_diffrn_orient_matrix_UB_23      0.0184451
_diffrn_orient_matrix_UB_33      0.0518375
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_reflns_av_R_equivalents  0.0837
_diffrn_reflns_av_unetI/netI     0.038
_diffrn_reflns_number            4974
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.81
_diffrn_reflns_theta_max         30.23
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.988
_reflns_Friedel_coverage         0
_reflns_number_total             4974
_reflns_number_gt                4125
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
 Scaled and merged with Sortav
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
 Slightly diorder H atom between the two atoms on the 
 chloranilic acid molecules, suggested also by the thermal 
 motion of O3 showing elongation
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0286P)²+0.4974P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4974
_refine_ls_number_parameters     283
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0332
_refine_ls_wR_factor_ref         0.0814
_refine_ls_wR_factor_gt          0.0775
_refine_ls_goodness_of_fit_ref   1.04
_refine_ls_restrained_S_all      1.04
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.609
_refine_diff_density_min         -0.526
_refine_diff_density_rms         0.062

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'

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 0.36765(5) 0.29834(4) 0.75146(3) 0.02226(9) Uani 1 1 d . . . . .
Cl2 Cl 0.29218(5) 0.53590(4) 0.16058(3) 0.02230(9) Uani 1 1 d . . . . .
Cl3 Cl 0.13189(4) 0.13193(4) 0.02046(3) 0.01906(8) Uani 1 1 d . . . . .
O2 O 0.53239(14) 0.19825(11) 0.55901(10) 0.0222(2) Uani 1 1 d . . . . .
O3 O 0.65796(19) 0.36418(13) 0.35386(12) 0.0389(3) Uani 1 1 d . . . . .
O12 O 0.29788(13) 0.58424(12) -0.10124(10) 0.0213(2) Uani 1 1 d . . . . .
O13 O -0.05363(15) 0.44513(12) 0.23787(9) 0.0228(2) Uani 1 1 d . . . . .
O32 O 0.24451(13) -0.13412(12) -0.05166(10) 0.0209(2) Uani 1 1 d . . . . .
O33 O 0.44558(13) 0.25605(11) 0.06558(10) 0.0194(2) Uani 1 1 d . . . . .
N125 N 0.73639(16) 0.02885(14) 0.45787(11) 0.0191(2) Uani 1 1 d . . . . .
C121 C 0.8956(2) -0.04520(18) 0.31235(14) 0.0231(3) Uani 1 1 d . . . . .
C122 C 0.94820(19) -0.17922(17) 0.39923(15) 0.0226(3) Uani 1 1 d . . . . .
C123 C 0.8879(2) -0.20464(17) 0.51449(14) 0.0232(3) Uani 1 1 d . . . . .
C124 C 0.7798(2) -0.09995(17) 0.54404(13) 0.0205(3) Uani 1 1 d . . . . .
C126 C 0.7905(2) 0.05692(17) 0.34426(14) 0.0214(3) Uani 1 1 d . . . . .
C22 C 1.0639(2) -0.2924(2) 0.3664(2) 0.0329(4) Uani 1 1 d . . . . .
C24 C 0.7079(2) -0.1250(2) 0.66618(15) 0.0274(3) Uani 1 1 d . . . . .
C111 C 0.43694(18) 0.40934(15) 0.61299(13) 0.0178(3) Uani 1 1 d . . . . .
C112 C 0.51411(18) 0.33752(16) 0.53636(13) 0.0177(3) Uani 1 1 d . . . . .
C113 C 0.58468(19) 0.43474(16) 0.41596(13) 0.0208(3) Uani 1 1 d . . . . .
C211 C 0.13201(18) 0.51595(15) 0.07445(13) 0.0179(3) Uani 1 1 d . . . . .
C212 C 0.16212(17) 0.54331(14) -0.04945(12) 0.0154(3) Uani 1 1 d . . . . .
C213 C -0.02202(18) 0.47394(14) 0.12534(12) 0.0156(3) Uani 1 1 d . . . . .
C311 C 0.33378(16) 0.06172(15) 0.01355(12) 0.0151(2) Uani 1 1 d . . . . .
C312 C 0.35807(17) -0.07085(15) -0.02502(12) 0.0151(2) Uani 1 1 d . . . . .
C313 C 0.46510(17) 0.13213(15) 0.03474(12) 0.0151(2) Uani 1 1 d . . . . .
H121 H 0.930(2) -0.026(2) 0.2351(18) 0.022(5) Uiso 1 1 d . . . . .
H123 H 0.918(2) -0.296(2) 0.5741(18) 0.025(5) Uiso 1 1 d . . . . .
H125 H 0.673(3) 0.102(3) 0.476(2) 0.038(6) Uiso 1 1 d . . . . .
H126 H 0.754(2) 0.152(2) 0.2906(18) 0.027(5) Uiso 1 1 d . . . . .
H22A H 1.103(3) -0.369(3) 0.435(2) 0.052(7) Uiso 1 1 d . . . . .
H22B H 1.008(3) -0.341(3) 0.325(2) 0.056(8) Uiso 1 1 d . . . . .
H22C H 1.154(3) -0.244(3) 0.319(2) 0.052(7) Uiso 1 1 d . . . . .
H24A H 0.788(3) -0.171(3) 0.724(2) 0.048(7) Uiso 1 1 d . . . . .
H24B H 0.613(3) -0.188(3) 0.678(2) 0.047(7) Uiso 1 1 d . . . . .
H24C H 0.671(3) -0.029(3) 0.680(2) 0.055(7) Uiso 1 1 d . . . . .
H33 H 0.536(3) 0.293(2) 0.0689(19) 0.030(5) Uiso 1 1 d . . . . .
H13 H -0.196(6) 0.418(6) 0.263(5) 0.169(19) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   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 C111 1.7381(14) . ?
Cl2 C211 1.7221(14) . ?
Cl3 C311 1.7185(13) . ?
O2 C112 1.2508(17) . ?
O3 C113 1.2476(19) . ?
O12 C212 1.2516(17) . ?
O13 C213 1.2939(17) . ?
O13 H13 1.19(5) . ?
O32 C312 1.2195(17) . ?
O33 C313 1.3254(16) . ?
O33 H33 0.83(2) . ?
N125 C126 1.349(2) . ?
N125 C124 1.3500(19) . ?
N125 H125 0.91(2) . ?
C121 C126 1.372(2) . ?
C121 C122 1.404(2) . ?
C121 H121 0.911(19) . ?
C122 C123 1.386(2) . ?
C122 C22 1.502(2) . ?
C123 C124 1.390(2) . ?
C123 H123 0.95(2) . ?
C124 C24 1.493(2) . ?
C126 H126 0.96(2) . ?
C22 H22A 0.95(3) . ?
C22 H22B 0.91(3) . ?
C22 H22C 0.95(3) . ?
C24 H24A 0.94(3) . ?
C24 H24B 0.97(3) . ?
C24 H24C 0.99(3) . ?
C111 C113 1.3968(19) 2_666 ?
C111 C112 1.400(2) . ?
C112 C113 1.542(2) . ?
C113 C111 1.3968(19) 2_666 ?
C211 C213 1.380(2) . ?
C211 C212 1.424(2) . ?
C212 C213 1.5099(19) 2_565 ?
C213 C212 1.5099(19) 2_565 ?
C311 C313 1.3485(19) . ?
C311 C312 1.4568(19) . ?
C312 C313 1.5110(18) 2_655 ?
C313 C312 1.5110(18) 2_655 ?

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
C213 O13 H13 113(2) . . ?
C313 O33 H33 112.4(14) . . ?
C126 N125 C124 122.28(13) . . ?
C126 N125 H125 117.7(14) . . ?
C124 N125 H125 119.9(14) . . ?
C126 C121 C122 119.45(15) . . ?
C126 C121 H121 119.6(12) . . ?
C122 C121 H121 120.9(12) . . ?
C123 C122 C121 118.16(14) . . ?
C123 C122 C22 121.48(15) . . ?
C121 C122 C22 120.35(16) . . ?
C122 C123 C124 121.16(14) . . ?
C122 C123 H123 119.8(12) . . ?
C124 C123 H123 119.1(12) . . ?
N125 C124 C123 118.37(14) . . ?
N125 C124 C24 118.77(14) . . ?
C123 C124 C24 122.85(14) . . ?
N125 C126 C121 120.55(14) . . ?
N125 C126 H126 115.4(12) . . ?
C121 C126 H126 124.0(12) . . ?
C122 C22 H22A 111.0(15) . . ?
C122 C22 H22B 110.4(16) . . ?
H22A C22 H22B 105(2) . . ?
C122 C22 H22C 110.3(15) . . ?
H22A C22 H22C 111(2) . . ?
H22B C22 H22C 109(2) . . ?
C124 C24 H24A 110.6(15) . . ?
C124 C24 H24B 109.8(14) . . ?
H24A C24 H24B 110(2) . . ?
C124 C24 H24C 111.9(15) . . ?
H24A C24 H24C 106(2) . . ?
H24B C24 H24C 109(2) . . ?
C113 C111 C112 123.16(13) 2_666 . ?
C113 C111 Cl1 118.76(11) 2_666 . ?
C112 C111 Cl1 118.07(11) . . ?
O2 C112 C111 124.54(13) . . ?
O2 C112 C113 116.81(13) . . ?
C111 C112 C113 118.64(12) . . ?
O3 C113 C111 126.29(14) . 2_666 ?
O3 C113 C112 115.55(13) . . ?
C111 C113 C112 118.16(13) 2_666 . ?
C213 C211 C212 121.03(13) . . ?
C213 C211 Cl2 120.26(11) . . ?
C212 C211 Cl2 118.71(11) . . ?
O12 C212 C211 124.10(13) . . ?
O12 C212 C213 116.99(12) . 2_565 ?
C211 C212 C213 118.90(12) . 2_565 ?
O13 C213 C211 123.00(13) . . ?
O13 C213 C212 116.92(12) . 2_565 ?
C211 C213 C212 120.07(12) . 2_565 ?
C313 C311 C312 121.17(12) . . ?
C313 C311 Cl3 121.50(11) . . ?
C312 C311 Cl3 117.16(10) . . ?
O32 C312 C311 123.99(13) . . ?
O32 C312 C313 117.96(12) . 2_655 ?
C311 C312 C313 118.04(11) . 2_655 ?
O33 C313 C311 122.04(12) . . ?
O33 C313 C312 117.25(12) . 2_655 ?
C311 C313 C312 120.72(12) . 2_655 ?

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
C126 C121 C122 C123 1.5(2) . . . . ?
C126 C121 C122 C22 -179.74(15) . . . . ?
C121 C122 C123 C124 -0.7(2) . . . . ?
C22 C122 C123 C124 -179.49(16) . . . . ?
C126 N125 C124 C123 1.9(2) . . . . ?
C126 N125 C124 C24 -177.14(15) . . . . ?
C122 C123 C124 N125 -0.9(2) . . . . ?
C122 C123 C124 C24 178.08(16) . . . . ?
C124 N125 C126 C121 -1.2(2) . . . . ?
C122 C121 C126 N125 -0.6(2) . . . . ?
C113 C111 C112 O2 -178.61(15) 2_666 . . . ?
Cl1 C111 C112 O2 2.3(2) . . . . ?
C113 C111 C112 C113 2.3(2) 2_666 . . . ?
Cl1 C111 C112 C113 -176.76(11) . . . . ?
O2 C112 C113 O3 -2.0(2) . . . . ?
C111 C112 C113 O3 177.16(15) . . . . ?
O2 C112 C113 C111 178.66(14) . . . 2_666 ?
C111 C112 C113 C111 -2.2(2) . . . 2_666 ?
C213 C211 C212 O12 178.67(13) . . . . ?
Cl2 C211 C212 O12 -1.46(19) . . . . ?
C213 C211 C212 C213 0.2(2) . . . 2_565 ?
Cl2 C211 C212 C213 -179.96(9) . . . 2_565 ?
C212 C211 C213 O13 178.59(13) . . . . ?
Cl2 C211 C213 O13 -1.28(19) . . . . ?
C212 C211 C213 C212 -0.2(2) . . . 2_565 ?
Cl2 C211 C213 C212 179.96(10) . . . 2_565 ?
C313 C311 C312 O32 -175.84(14) . . . . ?
Cl3 C311 C312 O32 -0.39(19) . . . . ?
C313 C311 C312 C313 3.0(2) . . . 2_655 ?
Cl3 C311 C312 C313 178.48(10) . . . 2_655 ?
C312 C311 C313 O33 177.44(13) . . . . ?
Cl3 C311 C313 O33 2.2(2) . . . . ?
C312 C311 C313 C312 -3.1(2) . . . 2_655 ?
Cl3 C311 C313 C312 -178.36(10) . . . 2_655 ?

####################################################################### 
# 
# 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_7_shelx
_database_code_depnum_ccdc_archive 'CCDC 1478101'
_audit_update_record             
;
2016-05-04 deposited with the CCDC.
2016-06-13 downloaded from the CCDC.
;

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         
;
C6 H Cl2 O4, 0.5(C6 H2 Cl2 O4), C7 H10 N
;
_chemical_formula_sum            'C16 H12 Cl3 N O6'
_chemical_formula_weight         420.62

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_space_group_crystal_system      Monoclinic
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14

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

_cell_length_a                   18.3393(5)
_cell_length_b                   4.95420(10)
_cell_length_c                   19.8433(5)
_cell_angle_alpha                90
_cell_angle_beta                 110.8690(10)
_cell_angle_gamma                90
_cell_volume                     1684.62(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4949
_cell_measurement_theta_min      2.197
_cell_measurement_theta_max      30.279
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       red
_exptl_crystal_colour            purple
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.17
_exptl_crystal_density_diffrn    1.661
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             856
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.58
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.0241
_exptl_absorpt_correction_T_max  0.7493
_exptl_absorpt_process_details   'SADABS, Bruker(2001)'

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_reflns_av_R_equivalents  0.0837
_diffrn_reflns_av_unetI/netI     0.03
_diffrn_reflns_number            4950
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       27
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_reflns_theta_min         2.197
_diffrn_reflns_theta_max         30.279
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.987
_reflns_Friedel_coverage         0
_reflns_number_total             4949
_reflns_number_gt                4533
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'


#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0251P)²+0.6466P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4949
_refine_ls_number_parameters     283
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0267
_refine_ls_R_factor_gt           0.0239
_refine_ls_wR_factor_ref         0.0652
_refine_ls_wR_factor_gt          0.0644
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.654
_refine_diff_density_min         -0.3
_refine_diff_density_rms         0.052

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'

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 0.23308(2) 0.63350(5) 0.46952(2) 0.01558(6) Uani 1 1 d . . . . .
Cl2 Cl -0.02790(2) -0.22954(5) 0.31488(2) 0.01487(6) Uani 1 1 d . . . . .
Cl3 Cl 0.37384(2) 0.07307(5) 0.50307(2) 0.01806(6) Uani 1 1 d . . . . .
O2 O 0.23309(4) 0.22444(15) 0.35501(4) 0.01550(14) Uani 1 1 d . . . . .
O3 O 0.12412(4) -0.14586(15) 0.29762(4) 0.01520(14) Uani 1 1 d . . . . .
O5 O -0.03135(4) 0.18015(16) 0.42236(4) 0.01706(14) Uani 1 1 d . . . . .
O6 O 0.08097(4) 0.53737(15) 0.48765(4) 0.01577(14) Uani 1 1 d . . . . .
O12 O 0.36114(4) 0.48372(16) 0.38353(4) 0.01734(14) Uani 1 1 d . . . . .
O13 O 0.47232(4) 0.82630(17) 0.38671(4) 0.01993(15) Uani 1 1 d . . . . .
N125 N 0.25409(5) -0.13019(19) 0.25416(5) 0.01691(17) Uani 1 1 d . . . . .
C121 C 0.35238(6) -0.1190(2) 0.20330(6) 0.0192(2) Uani 1 1 d . . . . .
C122 C 0.31174(6) -0.3191(2) 0.15581(5) 0.01854(19) Uani 1 1 d . . . . .
C123 C 0.24150(6) -0.4240(2) 0.15684(5) 0.01725(19) Uani 1 1 d . . . . .
C124 C 0.21374(6) -0.3229(2) 0.20833(5) 0.01732(19) Uani 1 1 d . . . . .
C126 C 0.32136(6) -0.0275(2) 0.25334(6) 0.01837(19) Uani 1 1 d . . . . .
C21 C 0.42648(7) 0.0001(3) 0.20024(8) 0.0305(3) Uani 1 1 d . . . . .
C23 C 0.19579(7) -0.6297(2) 0.10302(6) 0.0230(2) Uani 1 1 d . . . . .
C111 C 0.16337(5) 0.39356(19) 0.42650(5) 0.01228(16) Uani 1 1 d . . . . .
C112 C 0.17520(5) 0.22526(19) 0.37568(5) 0.01221(16) Uani 1 1 d . . . . .
C113 C 0.11243(5) 0.01179(19) 0.33999(5) 0.01189(16) Uani 1 1 d . . . . .
C114 C 0.04207(5) 0.00640(19) 0.35756(5) 0.01233(16) Uani 1 1 d . . . . .
C115 C 0.03262(5) 0.1811(2) 0.40588(5) 0.01267(17) Uani 1 1 d . . . . .
C116 C 0.09437(5) 0.38654(19) 0.44366(5) 0.01218(16) Uani 1 1 d . . . . .
C211 C 0.44037(5) 0.3130(2) 0.49945(5) 0.01394(17) Uani 1 1 d . . . . .
C212 C 0.42499(5) 0.4766(2) 0.44156(5) 0.01382(17) Uani 1 1 d . . . . .
C213 C 0.48588(5) 0.6785(2) 0.43891(5) 0.01394(17) Uani 1 1 d . . . . .
H122 H 0.3332(9) -0.389(3) 0.1209(8) 0.025(4) Uiso 1 1 d . . . . .
H124 H 0.1654(8) -0.376(3) 0.2121(7) 0.019(3) Uiso 1 1 d . . . . .
H125 H 0.2341(10) -0.070(4) 0.2865(9) 0.039(5) Uiso 1 1 d . . . . .
H126 H 0.3458(9) 0.103(3) 0.2893(8) 0.023(4) Uiso 1 1 d . . . . .
H21A H 0.4173(12) 0.172(4) 0.1811(10) 0.049(5) Uiso 1 1 d . . . . .
H21B H 0.4482(12) -0.112(4) 0.1724(11) 0.051(5) Uiso 1 1 d . . . . .
H21C H 0.4644(12) 0.022(4) 0.2477(11) 0.054(6) Uiso 1 1 d . . . . .
H23A H 0.1633(11) -0.544(4) 0.0598(10) 0.042(5) Uiso 1 1 d . . . . .
H23B H 0.1613(11) -0.733(4) 0.1185(10) 0.044(5) Uiso 1 1 d . . . . .
H23C H 0.2303(10) -0.748(4) 0.0927(9) 0.037(5) Uiso 1 1 d . . . . .
H5 H -0.0285(11) 0.299(4) 0.4525(9) 0.041(5) Uiso 1 1 d . . . . .
H12 H 0.3172(12) 0.384(4) 0.3855(11) 0.052(6) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   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 C111 1.7318(9) . ?
Cl2 C114 1.7193(10) . ?
Cl3 C211 1.7233(10) . ?
O2 C112 1.2671(11) . ?
O3 C113 1.2212(12) . ?
O5 C115 1.3254(11) . ?
O5 H5 0.829(19) . ?
O6 C116 1.2385(12) . ?
O12 C212 1.3183(12) . ?
O12 H12 0.96(2) . ?
O13 C213 1.2196(12) . ?
N125 C126 1.3400(14) . ?
N125 C124 1.3439(13) . ?
N125 H125 0.896(18) . ?
C121 C126 1.3847(15) . ?
C121 C122 1.3877(16) . ?
C121 C21 1.5023(16) . ?
C122 C123 1.3960(15) . ?
C122 H122 0.974(15) . ?
C123 C124 1.3874(14) . ?
C123 C23 1.4981(15) . ?
C124 H124 0.953(14) . ?
C126 H126 0.949(15) . ?
C21 H21A 0.92(2) . ?
C21 H21B 0.96(2) . ?
C21 H21C 0.96(2) . ?
C23 H23A 0.952(19) . ?
C23 H23B 0.945(19) . ?
C23 H23C 0.937(18) . ?
C111 C112 1.3839(13) . ?
C111 C116 1.4230(13) . ?
C112 C113 1.5376(13) . ?
C113 C114 1.4518(12) . ?
C114 C115 1.3480(13) . ?
C115 C116 1.5084(13) . ?
C211 C212 1.3509(13) . ?
C211 C213 1.4658(13) 3_666 ?
C212 C213 1.5140(13) . ?
C213 C211 1.4658(13) 3_666 ?

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
C115 O5 H5 110.0(13) . . ?
C212 O12 H12 116.7(12) . . ?
C126 N125 C124 123.29(9) . . ?
C126 N125 H125 119.7(11) . . ?
C124 N125 H125 117.0(11) . . ?
C126 C121 C122 117.53(10) . . ?
C126 C121 C21 120.60(11) . . ?
C122 C121 C21 121.85(10) . . ?
C121 C122 C123 122.09(9) . . ?
C121 C122 H122 118.8(9) . . ?
C123 C122 H122 119.1(9) . . ?
C124 C123 C122 117.31(10) . . ?
C124 C123 C23 120.79(10) . . ?
C122 C123 C23 121.86(10) . . ?
N125 C124 C123 119.79(10) . . ?
N125 C124 H124 116.5(9) . . ?
C123 C124 H124 123.6(9) . . ?
N125 C126 C121 119.98(10) . . ?
N125 C126 H126 116.1(9) . . ?
C121 C126 H126 123.9(9) . . ?
C121 C21 H21A 110.1(13) . . ?
C121 C21 H21B 111.1(12) . . ?
H21A C21 H21B 110.4(16) . . ?
C121 C21 H21C 110.8(12) . . ?
H21A C21 H21C 105.1(18) . . ?
H21B C21 H21C 109.1(17) . . ?
C123 C23 H23A 110.6(11) . . ?
C123 C23 H23B 113.9(11) . . ?
H23A C23 H23B 105.0(15) . . ?
C123 C23 H23C 109.4(10) . . ?
H23A C23 H23C 109.6(14) . . ?
H23B C23 H23C 108.3(15) . . ?
C112 C111 C116 122.90(8) . . ?
C112 C111 Cl1 119.53(7) . . ?
C116 C111 Cl1 117.52(7) . . ?
O2 C112 C111 127.21(9) . . ?
O2 C112 C113 115.14(8) . . ?
C111 C112 C113 117.64(8) . . ?
O3 C113 C114 122.86(9) . . ?
O3 C113 C112 118.08(8) . . ?
C114 C113 C112 119.06(8) . . ?
C115 C114 C113 120.63(8) . . ?
C115 C114 Cl2 121.63(7) . . ?
C113 C114 Cl2 117.74(7) . . ?
O5 C115 C114 121.51(9) . . ?
O5 C115 C116 116.98(8) . . ?
C114 C115 C116 121.51(8) . . ?
O6 C116 C111 124.79(9) . . ?
O6 C116 C115 117.06(8) . . ?
C111 C116 C115 118.15(8) . . ?
C212 C211 C213 122.93(9) . 3_666 ?
C212 C211 Cl3 120.85(7) . . ?
C213 C211 Cl3 116.20(7) 3_666 . ?
O12 C212 C211 127.61(9) . . ?
O12 C212 C213 112.86(8) . . ?
C211 C212 C213 119.52(8) . . ?
O13 C213 C211 122.68(9) . 3_666 ?
O13 C213 C212 119.77(9) . . ?
C211 C213 C212 117.56(8) 3_666 . ?

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
C126 C121 C122 C123 0.96(16) . . . . ?
C21 C121 C122 C123 -177.81(11) . . . . ?
C121 C122 C123 C124 -0.88(16) . . . . ?
C121 C122 C123 C23 176.80(10) . . . . ?
C126 N125 C124 C123 -0.21(16) . . . . ?
C122 C123 C124 N125 0.49(15) . . . . ?
C23 C123 C124 N125 -177.22(10) . . . . ?
C124 N125 C126 C121 0.30(16) . . . . ?
C122 C121 C126 N125 -0.65(16) . . . . ?
C21 C121 C126 N125 178.14(11) . . . . ?
C116 C111 C112 O2 177.04(9) . . . . ?
Cl1 C111 C112 O2 -0.52(14) . . . . ?
C116 C111 C112 C113 -3.60(14) . . . . ?
Cl1 C111 C112 C113 178.84(7) . . . . ?
O2 C112 C113 O3 2.83(13) . . . . ?
C111 C112 C113 O3 -176.61(9) . . . . ?
O2 C112 C113 C114 -176.88(8) . . . . ?
C111 C112 C113 C114 3.68(13) . . . . ?
O3 C113 C114 C115 178.57(9) . . . . ?
C112 C113 C114 C115 -1.73(14) . . . . ?
O3 C113 C114 Cl2 -1.32(13) . . . . ?
C112 C113 C114 Cl2 178.38(7) . . . . ?
C113 C114 C115 O5 179.68(9) . . . . ?
Cl2 C114 C115 O5 -0.43(14) . . . . ?
C113 C114 C115 C116 -0.36(14) . . . . ?
Cl2 C114 C115 C116 179.53(7) . . . . ?
C112 C111 C116 O6 -178.44(9) . . . . ?
Cl1 C111 C116 O6 -0.84(13) . . . . ?
C112 C111 C116 C115 1.59(14) . . . . ?
Cl1 C111 C116 C115 179.19(7) . . . . ?
O5 C115 C116 O6 0.56(13) . . . . ?
C114 C115 C116 O6 -179.40(9) . . . . ?
O5 C115 C116 C111 -179.47(8) . . . . ?
C114 C115 C116 C111 0.57(14) . . . . ?
C213 C211 C212 O12 179.51(9) 3_666 . . . ?
Cl3 C211 C212 O12 1.44(15) . . . . ?
C213 C211 C212 C213 0.25(16) 3_666 . . . ?
Cl3 C211 C212 C213 -177.82(7) . . . . ?
O12 C212 C213 O13 0.52(13) . . . . ?
C211 C212 C213 O13 179.88(10) . . . . ?
O12 C212 C213 C211 -179.60(8) . . . 3_666 ?
C211 C212 C213 C211 -0.24(15) . . . 3_666 ?

