# 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_atrazine_microsource_fdd2
_audit_block_doi                 10.5517/cc13m41x
_database_code_depnum_ccdc_archive 'CCDC 1031278'
_audit_update_record             
;
2014-10-28 deposited with the CCDC.
2016-01-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H14 Cl N5'
_chemical_formula_weight         215.69

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'

_cell_length_a                   34.2012(19)
_cell_length_b                   10.3247(6)
_cell_length_c                   12.1234(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4281.0(4)
_cell_formula_units_Z            16
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5329
_cell_measurement_theta_min      2.382
_cell_measurement_theta_max      29.792

_exptl_crystal_description       'Thin plates'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_F_000             1824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.254
_exptl_crystal_size_mid          0.058
_exptl_crystal_size_min          0.042
_exptl_absorpt_coefficient_mu    0.328
_shelx_estimated_absorpt_T_min   0.921
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.921
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   'SADABS (Bruker, 2001)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec I\mS microfocus X-ray source'
_diffrn_measurement_device_type  'Bruker kappa APEXII CCD Diffractometer'
_diffrn_measurement_method       'φ scans, and ω scans with κ offsets'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13347
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.659
_diffrn_reflns_theta_max         24.976
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_point_group_measured_fraction_full 0.924
_reflns_number_total             1786
_reflns_number_gt                1629
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.791
_reflns_Friedel_fraction_max     0.877
_reflns_Friedel_fraction_full    0.861

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'APEX2 (Bruker, 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL-Plus (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0777P)²+8.8230P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 672 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.69(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1786
_refine_ls_number_parameters     130
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0442
_refine_ls_wR_factor_ref         0.1182
_refine_ls_wR_factor_gt          0.1126
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 1.04945(3) 0.58094(11) 0.48071(8) 0.0324(3) Uani 1 1 d . . . . .
N1 N 1.00436(11) 0.7409(4) 0.5858(3) 0.0272(9) Uani 1 1 d . . . . .
N2 N 0.95596(10) 0.8715(4) 0.4922(4) 0.0279(8) Uani 1 1 d . . . . .
N3 N 0.99710(11) 0.7264(4) 0.3907(3) 0.0249(9) Uani 1 1 d . . . . .
N4 N 0.96653(13) 0.8857(4) 0.6806(3) 0.0353(10) Uani 1 1 d . . . . .
H4 H 0.9788 0.8579 0.7400 0.042 Uiso 1 1 calc R U . . .
N5 N 0.95006(11) 0.8469(4) 0.3054(3) 0.0347(10) Uani 1 1 d . . . . .
H5 H 0.9583 0.8109 0.2439 0.042 Uiso 1 1 calc R U . . .
C1 C 1.01239(10) 0.6976(4) 0.4858(4) 0.0223(8) Uani 1 1 d . . . . .
C2 C 0.97530(13) 0.8313(5) 0.5836(4) 0.0261(10) Uani 1 1 d . . . . .
C3 C 0.96805(12) 0.8158(5) 0.3985(4) 0.0253(10) Uani 1 1 d . . . . .
C4 C 0.93768(16) 0.9887(5) 0.6930(4) 0.0395(12) Uani 1 1 d . . . . .
H4A H 0.9381 1.0444 0.6265 0.047 Uiso 1 1 calc R U . . .
H4B H 0.9447 1.0431 0.7572 0.047 Uiso 1 1 calc R U . . .
C5 C 0.89730(17) 0.9358(6) 0.7089(5) 0.0527(17) Uani 1 1 d . . . . .
H5A H 0.8900 0.8838 0.6445 0.079 Uiso 1 1 calc R U . . .
H5B H 0.8788 1.0076 0.7174 0.079 Uiso 1 1 calc R U . . .
H5C H 0.8967 0.8815 0.7751 0.079 Uiso 1 1 calc R U . . .
C6 C 0.91737(14) 0.9373(5) 0.2987(4) 0.0346(12) Uani 1 1 d . . . . .
H6 H 0.9069 0.9493 0.3750 0.041 Uiso 1 1 calc R U . . .
C7 C 0.93146(17) 1.0685(5) 0.2579(5) 0.0473(14) Uani 1 1 d . . . . .
H7A H 0.9431 1.0589 0.1845 0.071 Uiso 1 1 calc R U . . .
H7B H 0.9511 1.1029 0.3090 0.071 Uiso 1 1 calc R U . . .
H7C H 0.9093 1.1284 0.2538 0.071 Uiso 1 1 calc R U . . .
C8 C 0.88519(13) 0.8817(5) 0.2292(5) 0.0410(12) Uani 1 1 d . . . . .
H8A H 0.8630 0.9417 0.2283 0.062 Uiso 1 1 calc R U . . .
H8B H 0.8769 0.7985 0.2602 0.062 Uiso 1 1 calc R U . . .
H8C H 0.8947 0.8687 0.1538 0.062 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C1 1.750(4) . ?
N1 C1 1.321(6) . ?
N1 C2 1.364(6) . ?
N2 C3 1.339(7) . ?
N2 C2 1.355(6) . ?
N3 C1 1.301(6) . ?
N3 C3 1.360(6) . ?
N4 C2 1.337(6) . ?
N4 C4 1.459(7) . ?
N4 H4 0.8800 . ?
N5 C3 1.325(6) . ?
N5 C6 1.458(6) . ?
N5 H5 0.8800 . ?
C4 C5 1.498(8) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C8 1.500(7) . ?
C6 C7 1.522(8) . ?
C6 H6 1.0000 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C2 111.5(4) . . ?
C3 N2 C2 114.3(4) . . ?
C1 N3 C3 112.8(4) . . ?
C2 N4 C4 123.2(4) . . ?
C2 N4 H4 118.4 . . ?
C4 N4 H4 118.4 . . ?
C3 N5 C6 123.9(4) . . ?
C3 N5 H5 118.0 . . ?
C6 N5 H5 118.0 . . ?
N3 C1 N1 130.7(4) . . ?
N3 C1 Cl1 114.7(3) . . ?
N1 C1 Cl1 114.6(3) . . ?
N4 C2 N2 118.8(4) . . ?
N4 C2 N1 115.7(4) . . ?
N2 C2 N1 125.5(4) . . ?
N5 C3 N2 118.4(4) . . ?
N5 C3 N3 116.4(4) . . ?
N2 C3 N3 125.2(4) . . ?
N4 C4 C5 111.8(5) . . ?
N4 C4 H4A 109.3 . . ?
C5 C4 H4A 109.3 . . ?
N4 C4 H4B 109.3 . . ?
C5 C4 H4B 109.3 . . ?
H4A C4 H4B 107.9 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N5 C6 C8 110.5(4) . . ?
N5 C6 C7 110.2(4) . . ?
C8 C6 C7 113.0(4) . . ?
N5 C6 H6 107.7 . . ?
C8 C6 H6 107.7 . . ?
C7 C6 H6 107.7 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N3 C1 N1 -0.3(7) . . . . ?
C3 N3 C1 Cl1 179.1(3) . . . . ?
C2 N1 C1 N3 -0.7(7) . . . . ?
C2 N1 C1 Cl1 180.0(3) . . . . ?
C4 N4 C2 N2 -1.5(7) . . . . ?
C4 N4 C2 N1 176.8(5) . . . . ?
C3 N2 C2 N4 177.0(4) . . . . ?
C3 N2 C2 N1 -1.1(7) . . . . ?
C1 N1 C2 N4 -176.7(4) . . . . ?
C1 N1 C2 N2 1.4(7) . . . . ?
C6 N5 C3 N2 -0.8(7) . . . . ?
C6 N5 C3 N3 177.7(4) . . . . ?
C2 N2 C3 N5 178.3(4) . . . . ?
C2 N2 C3 N3 -0.1(6) . . . . ?
C1 N3 C3 N5 -177.7(4) . . . . ?
C1 N3 C3 N2 0.7(7) . . . . ?
C2 N4 C4 C5 87.3(6) . . . . ?
C3 N5 C6 C8 -133.1(5) . . . . ?
C3 N5 C6 C7 101.4(6) . . . . ?

_refine_diff_density_max         0.484
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.064

_shelxl_version_number           2014-3

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

data_JBsimazine
_audit_block_doi                 10.5517/cc13m42y
_database_code_depnum_ccdc_archive 'CCDC 1031279'
_audit_update_record             
;
2014-10-28 deposited with the CCDC.
2016-01-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H12 Cl N5'
_chemical_formula_weight         201.67

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

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   4.4390(9)
_cell_length_b                   11.980(2)
_cell_length_c                   17.852(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.04(3)
_cell_angle_gamma                90
_cell_volume                     947.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5664
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      22.5

_exptl_crystal_description       plates
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_F_000             424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.020
_exptl_crystal_size_mid          0.015
_exptl_crystal_size_min          0.015
_exptl_absorpt_coefficient_mu    0.365
_shelx_estimated_absorpt_T_min   0.993
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Synchrotron BM'
_diffrn_radiation_monochromator  Si<111>
_diffrn_measurement_device_type  '3-BM1 Australian Synchrotron'
_diffrn_measurement_method       'Phi Scan'
_diffrn_detector_type            'ADSC Quantum 210r'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            11560
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.049
_diffrn_reflns_theta_max         24.989
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measured_fraction_theta_full 0.932
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_Laue_measured_fraction_full 0.932
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_point_group_measured_fraction_full 0.932
_reflns_number_total             1601
_reflns_number_gt                1496
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0907P)²+0.4483P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1601
_refine_ls_number_parameters     120
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0437
_refine_ls_wR_factor_ref         0.1304
_refine_ls_wR_factor_gt          0.1280
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 1.32210(10) 0.62018(3) 0.64572(2) 0.0183(2) Uani 1 1 d . . . . .
N1 N 1.0073(3) 0.71968(13) 0.74303(8) 0.0153(4) Uani 1 1 d . . . . .
N2 N 0.7118(3) 0.61981(10) 0.82942(9) 0.0158(4) Uani 1 1 d . . . . .
N3 N 0.9948(3) 0.52017(13) 0.74007(8) 0.0154(4) Uani 1 1 d . . . . .
N4 N 0.7282(3) 0.81259(12) 0.82525(8) 0.0158(4) Uani 1 1 d . . . . .
H4 H 0.7946 0.8717 0.8046 0.019 Uiso 1 1 calc R U . . .
N5 N 0.7005(3) 0.42733(12) 0.81918(8) 0.0159(4) Uani 1 1 d . . . . .
H5 H 0.7566 0.3683 0.7965 0.019 Uiso 1 1 calc R U . . .
C1 C 1.0776(4) 0.61995(12) 0.71899(10) 0.0144(4) Uani 1 1 d . . . . .
C2 C 0.8148(4) 0.71415(14) 0.79971(9) 0.0146(4) Uani 1 1 d . . . . .
C3 C 0.8018(4) 0.52536(14) 0.79675(9) 0.0148(4) Uani 1 1 d . . . . .
C4 C 0.5282(4) 0.82670(15) 0.88597(9) 0.0179(4) Uani 1 1 d . . . . .
H4A H 0.4085 0.7596 0.8904 0.021 Uiso 1 1 calc R U . . .
H4B H 0.3909 0.8882 0.8740 0.021 Uiso 1 1 calc R U . . .
C5 C 0.7038(5) 0.84980(19) 0.96037(10) 0.0285(5) Uani 1 1 d . . . . .
H5A H 0.8255 0.9154 0.9559 0.043 Uiso 1 1 calc R U . . .
H5B H 0.8316 0.7872 0.9737 0.043 Uiso 1 1 calc R U . . .
H5C H 0.5653 0.8614 0.9986 0.043 Uiso 1 1 calc R U . . .
C6 C 0.5000(4) 0.41375(15) 0.87982(9) 0.0169(4) Uani 1 1 d . . . . .
H6A H 0.3637 0.3519 0.8682 0.020 Uiso 1 1 calc R U . . .
H6B H 0.3793 0.4807 0.8837 0.020 Uiso 1 1 calc R U . . .
C7 C 0.6755(5) 0.39199(16) 0.95450(11) 0.0234(5) Uani 1 1 d . . . . .
H7A H 0.7961 0.3260 0.9507 0.035 Uiso 1 1 calc R U . . .
H7B H 0.5369 0.3817 0.9928 0.035 Uiso 1 1 calc R U . . .
H7C H 0.8044 0.4545 0.9672 0.035 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C1 1.7576(19) . ?
N1 C1 1.315(2) . ?
N1 C2 1.372(2) . ?
N2 C2 1.342(2) . ?
N2 C3 1.347(2) . ?
N3 C1 1.313(2) . ?
N3 C3 1.372(2) . ?
N4 C2 1.331(2) . ?
N4 C4 1.459(2) . ?
N4 H4 0.8600 . ?
N5 C3 1.329(2) . ?
N5 C6 1.458(2) . ?
N5 H5 0.8600 . ?
C4 C5 1.517(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C7 1.519(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C2 111.81(14) . . ?
C2 N2 C3 114.62(16) . . ?
C1 N3 C3 111.84(14) . . ?
C2 N4 C4 124.26(14) . . ?
C2 N4 H4 117.9 . . ?
C4 N4 H4 117.9 . . ?
C3 N5 C6 124.01(14) . . ?
C3 N5 H5 118.0 . . ?
C6 N5 H5 118.0 . . ?
N3 C1 N1 131.00(17) . . ?
N3 C1 Cl1 114.50(12) . . ?
N1 C1 Cl1 114.50(12) . . ?
N4 C2 N2 119.74(15) . . ?
N4 C2 N1 114.84(15) . . ?
N2 C2 N1 125.42(15) . . ?
N5 C3 N2 119.66(15) . . ?
N5 C3 N3 115.10(15) . . ?
N2 C3 N3 125.24(15) . . ?
N4 C4 C5 111.69(14) . . ?
N4 C4 H4A 109.3 . . ?
C5 C4 H4A 109.3 . . ?
N4 C4 H4B 109.3 . . ?
C5 C4 H4B 109.3 . . ?
H4A C4 H4B 107.9 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N5 C6 C7 111.64(14) . . ?
N5 C6 H6A 109.3 . . ?
C7 C6 H6A 109.3 . . ?
N5 C6 H6B 109.3 . . ?
C7 C6 H6B 109.3 . . ?
H6A C6 H6B 108.0 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N3 C1 N1 0.2(3) . . . . ?
C3 N3 C1 Cl1 -179.33(10) . . . . ?
C2 N1 C1 N3 0.0(3) . . . . ?
C2 N1 C1 Cl1 179.57(10) . . . . ?
C4 N4 C2 N2 1.3(2) . . . . ?
C4 N4 C2 N1 -179.04(14) . . . . ?
C3 N2 C2 N4 176.80(14) . . . . ?
C3 N2 C2 N1 -2.9(2) . . . . ?
C1 N1 C2 N4 -178.28(14) . . . . ?
C1 N1 C2 N2 1.4(2) . . . . ?
C6 N5 C3 N2 -1.9(2) . . . . ?
C6 N5 C3 N3 178.34(13) . . . . ?
C2 N2 C3 N5 -176.56(14) . . . . ?
C2 N2 C3 N3 3.1(2) . . . . ?
C1 N3 C3 N5 177.81(14) . . . . ?
C1 N3 C3 N2 -1.9(2) . . . . ?
C2 N4 C4 C5 98.3(2) . . . . ?
C3 N5 C6 C7 -93.45(19) . . . . ?

_refine_diff_density_max         0.826
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.070

_shelxl_version_number           2014-3

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

data_atrazine_pca21_a
_database_code_depnum_ccdc_archive 'CCDC 1435451'
_audit_update_record             
;
2015-11-06 deposited with the CCDC.
2016-01-04 downloaded from the CCDC.
;
_audit_creation_date             2015-09-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C8 H14 Cl N5)'
_chemical_formula_sum            'C16 H28 Cl2 N10'
_chemical_formula_weight         431.38
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   19.847(4)
_cell_length_b                   9.6160(19)
_cell_length_c                   23.793(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4540.9(16)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    100
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.309
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1824
_exptl_crystal_size_max          0.015
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1568
_diffrn_reflns_av_unetI/netI     0.0487
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            34417
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        21.325
_diffrn_reflns_theta_max         21.325
_diffrn_reflns_theta_min         1.712
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Australian Synchrotron'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1657
_reflns_number_total             2548
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.141
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         2548
_refine_ls_number_restraints     46
_refine_ls_R_factor_all          0.1520
_refine_ls_R_factor_gt           0.1101
_refine_ls_restrained_S_all      1.137
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0430P)²+40.7579P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2366
_refine_ls_wR_factor_ref         0.2566
_refine_special_details          ?
_olex2_refinement_description    
;
1. Shared sites
{H4AA, H4A}
{H5AA, H5A}
{C4A, C6A'}
{C7A', C5A}
{C4A', C6A}
{H4AE, H6A}
{C5A', C7A}
2. Others
 Fixed Sof: Cl1"(0.5) Cl1B(0.5) C4B(0.6) H4BA(0.6) H4BB(0.6) C5B(0.6)
 H5BA(0.6) H5BB(0.6) H5BC(0.6) C4B'(0.4) H4BC(0.4) H4BD(0.4) C5B'(0.4)
 H5BD(0.4) H5BE(0.4) H5BF(0.4) H4A(0.5) H4AA(0.5) H5A(0.5) C4A(0.5) H4AB(0.5)
 H4AC(0.5) C6A'(0.5) C5A(0.5) H5AB(0.5) H5AC(0.5) H5AD(0.5) C6A(0.5) H6A(0.5)
 C7A(0.5) H7AA(0.5) H7AB(0.5) H7AC(0.5) C8A(0.5) H8AA(0.5) H8AB(0.5) H8AC(0.5)
 C4A'(0.5) H4AD(0.5) H4AE(0.5) C5A'(0.5) H5AE(0.5) H5AF(0.5) H5AG(0.5)
 C7A'(0.5) H7AD(0.5) H7AE(0.5) H7AF(0.5) C8A'(0.5) H8AD(0.5) H8AE(0.5) H8AF(0.5)
 Fixed Uiso: H4B(0.081) H5B(0.081) H4BA(0.053) H4BB(0.053) H5BA(0.096)
 H5BB(0.096) H5BC(0.096) H6B(0.089) H7BA(0.155) H7BB(0.155) H7BC(0.155)
 H8BA(0.13) H8BB(0.13) H8BC(0.13) H4BC(0.102) H4BD(0.102) H5BD(0.208)
 H5BE(0.208) H5BF(0.208) H4A(0.078) H4AA(0.078) H5A(0.072) H5AA(0.072)
 H4AB(0.089) H4AC(0.089) H5AB(0.144) H5AC(0.144) H5AD(0.144) H6A(0.08)
 H7AA(0.139) H7AB(0.139) H7AC(0.139) H8AA(0.121) H8AB(0.121) H8AC(0.121)
 H4AD(0.08) H4AE(0.08) H5AE(0.139) H5AF(0.139) H5AG(0.139) H7AD(0.144)
 H7AE(0.144) H7AF(0.144) H8AD(0.177) H8AE(0.177) H8AF(0.177)
 Fixed X: H4B(1.0599) H5B(1.0539) H4BA(0.9426) H4BB(0.9482) H5BA(0.9468)
 H5BB(0.9439) H5BC(0.8812) H6B(0.9364) H7BA(0.9495) H7BB(0.8825) H7BC(0.9486)
 H8BA(0.9576) H8BB(0.8854) H8BC(0.946) H4BC(0.9516) H4BD(0.9329) H5BD(0.9029)
 H5BE(0.9815) H5BF(0.9491) H4A(1.1779) H4AA(1.1779) H5A(1.1883) H5AA(1.1883)
 H4AB(1.2522) H4AC(1.2548) H5AB(1.3585) H5AC(1.325) H5AD(1.3243) H6A(1.2642)
 H7AA(1.3325) H7AB(1.3279) H7AC(1.3677) H8AA(1.228) H8AB(1.3071) H8AC(1.2542)
 H4AD(1.2632) H4AE(1.2642) H5AE(1.3512) H5AF(1.3589) H5AG(1.318) H7AD(1.3172)
 H7AE(1.3563) H7AF(1.3343) H8AD(1.2403) H8AE(1.2882) H8AF(1.2087)
 Fixed Y: H4B(0.7809) H5B(0.7465) H4BA(0.6954) H4BB(0.7147) H5BA(0.943)
 H5BB(0.9546) H5BC(0.8918) H6B(0.7047) H7BA(0.9508) H7BB(0.9003) H7BC(0.9372)
 H8BA(0.6905) H8BB(0.6658) H8BC(0.5604) H4BC(0.8769) H4BD(0.7378) H5BD(0.9459)
 H5BE(0.978) H5BF(0.8437) H4A(0.6517) H4AA(0.6517) H5A(0.6611) H5AA(0.6611)
 H4AB(0.4741) H4AC(0.4524) H5AB(0.5302) H5AC(0.6609) H5AD(0.6511) H6A(0.466)
 H7AA(0.6625) H7AB(0.6938) H7AC(0.5596) H8AA(0.398) H8AB(0.4246) H8AC(0.537)
 H4AD(0.4862) H4AE(0.4668) H5AE(0.6202) H5AF(0.5796) H5AG(0.7162) H7AD(0.6795)
 H7AE(0.5356) H7AF(0.6271) H8AD(0.5251) H8AE(0.4011) H8AF(0.3927)
 Fixed Z: H4B(0.4427) H5B(0.1879) H4BA(0.3871) H4BB(0.454) H5BA(0.3778)
 H5BB(0.4449) H5BC(0.411) H6B(0.2503) H7BA(0.2422) H7BB(0.2107) H7BC(0.1751)
 H8BA(0.1312) H8BB(0.1594) H8BC(0.172) H4BC(0.384) H4BD(0.4172) H5BD(0.4659)
 H5BE(0.4733) H5BF(0.5024) H4A(0.1919) H4AA(0.1919) H5A(-0.0612) H5AA(-0.0612)
 H4AB(0.2045) H4AC(0.1378) H5AB(0.1672) H5AC(0.198) H5AD(0.1309) H6A(-0.0039)
 H7AA(0.0059) H7AB(-0.06) H7AC(-0.0381) H8AA(-0.0868) H8AB(-0.094) H8AC(-
 0.1167) H4AD(-0.0711) H4AE(-0.0042) H5AE(-0.0681) H5AF(-0.0032) H5AG(-0.0208)
 H7AD(0.1416) H7AE(0.1507) H7AF(0.2038) H8AD(0.2507) H8AE(0.2303) H8AF(0.2197)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 1.2467(3) 0.6891(11) 0.3177(3) 0.082(3) Uani 0.5 1 d D U P A 3
Cl1B Cl 1.2485(3) 0.7949(9) 0.3073(3) 0.068(2) Uani 0.5 1 d D U P A 1
N1B N 1.1346(4) 0.7655(13) 0.3646(3) 0.080(4) Uani 1 1 d . U . . .
N2B N 1.0278(4) 0.7648(11) 0.3162(3) 0.062(3) Uani 1 1 d . . . . .
N3B N 1.1309(4) 0.7469(14) 0.2643(3) 0.085(4) Uani 1 1 d . . . . .
N4B N 1.0353(4) 0.7710(11) 0.4122(3) 0.068(3) Uani 1 1 d D U . . .
H4B H 1.0599 0.7809 0.4427 0.081 Uiso 1 1 calc R . . B 1
N5B N 1.0304(4) 0.7492(11) 0.2193(3) 0.068(3) Uani 1 1 d . . . . .
H5B H 1.0539 0.7465 0.1879 0.081 Uiso 1 1 calc R . . . .
C1B C 1.1598(5) 0.7535(17) 0.3129(5) 0.091(4) Uani 1 1 d D U . . .
C2B C 1.0647(5) 0.7695(14) 0.3629(4) 0.062(3) Uani 1 1 d . . . . .
C3B C 1.0633(5) 0.7555(14) 0.2676(4) 0.062(3) Uani 1 1 d . . . . .
C4B C 0.9601(7) 0.756(3) 0.4173(14) 0.044(5) Uani 0.6 1 d D U P C 1
H4BA H 0.9426 0.6954 0.3871 0.053 Uiso 0.6 1 calc R . P C 1
H4BB H 0.9482 0.7147 0.4540 0.053 Uiso 0.6 1 calc R . P C 1
C5B C 0.9304(9) 0.899(2) 0.4123(8) 0.064(5) Uani 0.6 1 d D . P C 1
H5BA H 0.9468 0.9430 0.3778 0.096 Uiso 0.6 1 calc GR . P C 1
H5BB H 0.9439 0.9546 0.4449 0.096 Uiso 0.6 1 calc GR . P C 1
H5BC H 0.8812 0.8918 0.4110 0.096 Uiso 0.6 1 calc GR . P C 1
C6B C 0.9554(5) 0.7463(15) 0.2152(5) 0.074(4) Uani 1 1 d . . . . .
H6B H 0.9364 0.7047 0.2503 0.089 Uiso 1 1 calc R . . . .
C7B C 0.9319(7) 0.8972(16) 0.2104(6) 0.103(5) Uani 1 1 d . . . . .
H7BA H 0.9495 0.9508 0.2422 0.155 Uiso 1 1 calc GR . . . .
H7BB H 0.8825 0.9003 0.2107 0.155 Uiso 1 1 calc GR . . . .
H7BC H 0.9486 0.9372 0.1751 0.155 Uiso 1 1 calc GR . . . .
C8B C 0.9342(6) 0.6578(15) 0.1649(5) 0.087(4) Uani 1 1 d . . . . .
H8BA H 0.9576 0.6905 0.1312 0.130 Uiso 1 1 calc GR . . . .
H8BB H 0.8854 0.6658 0.1594 0.130 Uiso 1 1 calc GR . . . .
H8BC H 0.9460 0.5604 0.1720 0.130 Uiso 1 1 calc GR . . . .
C4B' C 0.9628(10) 0.820(6) 0.417(2) 0.09(2) Uani 0.4 1 d D U P C 2
H4BC H 0.9516 0.8769 0.3840 0.102 Uiso 0.4 1 calc R . P C 2
H4BD H 0.9329 0.7378 0.4172 0.102 Uiso 0.4 1 calc R . P C 2
C5B' C 0.9478(17) 0.904(5) 0.4693(15) 0.14(2) Uani 0.4 1 d D U P C 2
H5BD H 0.9029 0.9459 0.4659 0.208 Uiso 0.4 1 calc GR . P C 2
H5BE H 0.9815 0.9780 0.4733 0.208 Uiso 0.4 1 calc GR . P C 2
H5BF H 0.9491 0.8437 0.5024 0.208 Uiso 0.4 1 calc GR . P C 2
Cl1A Cl 1.02845(13) 0.8943(3) 0.06159(13) 0.0719(9) Uani 1 1 d . . . . .
N1A N 1.1198(4) 0.7490(9) 0.1148(3) 0.047(2) Uani 1 1 d . . . . .
N2A N 1.2066(3) 0.6248(8) 0.0656(3) 0.044(2) Uani 1 1 d . . . . .
N3A N 1.1227(4) 0.7527(9) 0.0145(3) 0.048(2) Uani 1 1 d . . . . .
N4A N 1.1980(4) 0.6213(11) 0.1613(3) 0.065(3) Uani 1 1 d . . . . .
H4A H 1.1779 0.6517 0.1919 0.078 Uiso 0.5 1 calc R . P D 1
H4AA H 1.1779 0.6517 0.1919 0.078 Uiso 0.5 1 calc R . P E 2
N5A N 1.2062(4) 0.6295(10) -0.0298(3) 0.060(3) Uani 1 1 d . . . . .
H5A H 1.1883 0.6611 -0.0612 0.072 Uiso 0.5 1 calc R . P F 1
H5AA H 1.1883 0.6611 -0.0612 0.072 Uiso 1 1 calc R . . G 2
C1A C 1.0993(4) 0.7842(10) 0.0648(5) 0.049(3) Uani 1 1 d . . . . .
C2A C 1.1748(5) 0.6655(12) 0.1116(4) 0.045(3) Uani 1 1 d . . . . .
C3A C 1.1784(5) 0.6693(11) 0.0180(4) 0.046(3) Uani 1 1 d . . . . .
C4A C 1.2562(5) 0.5230(14) 0.1681(4) 0.074(4) Uani 0.5 1 d D U P H 1
H4AB H 1.2522 0.4741 0.2045 0.089 Uiso 0.5 1 calc R . P H 1
H4AC H 1.2548 0.4524 0.1378 0.089 Uiso 0.5 1 calc R . P H 1
C6A' C 1.2562(5) 0.5230(14) 0.1681(4) 0.074(4) Uani 0.5 1 d D U P H 2
C5A C 1.3216(6) 0.5976(17) 0.1658(6) 0.096(4) Uani 0.5 1 d D U P H 1
H5AB H 1.3585 0.5302 0.1672 0.144 Uiso 0.5 1 calc GR . P H 1
H5AC H 1.3250 0.6609 0.1980 0.144 Uiso 0.5 1 calc GR . P H 1
H5AD H 1.3243 0.6511 0.1309 0.144 Uiso 0.5 1 calc GR . P H 1
C6A C 1.2650(5) 0.5364(14) -0.0348(4) 0.067(3) Uani 0.5 1 d . U P I 1
H6A H 1.2642 0.4660 -0.0039 0.080 Uiso 0.5 1 calc R . P I 1
C7A C 1.3288(6) 0.6204(17) -0.0314(5) 0.093(4) Uani 0.5 1 d . U P I 1
H7AA H 1.3325 0.6625 0.0059 0.139 Uiso 0.5 1 calc GR . P I 1
H7AB H 1.3279 0.6938 -0.0600 0.139 Uiso 0.5 1 calc GR . P I 1
H7AC H 1.3677 0.5596 -0.0381 0.139 Uiso 0.5 1 calc GR . P I 1
C8A C 1.2635(13) 0.469(3) -0.0870(8) 0.081(7) Uani 0.5 1 d . U P I 1
H8AA H 1.2280 0.3980 -0.0868 0.121 Uiso 0.5 1 calc GR . P I 1
H8AB H 1.3071 0.4246 -0.0940 0.121 Uiso 0.5 1 calc GR . P I 1
H8AC H 1.2542 0.5370 -0.1167 0.121 Uiso 0.5 1 calc GR . P I 1
C4A' C 1.2650(5) 0.5364(14) -0.0348(4) 0.067(3) Uani 0.5 1 d . U P I 2
H4AD H 1.2632 0.4862 -0.0711 0.080 Uiso 0.5 1 calc R . P I 2
H4AE H 1.2642 0.4668 -0.0042 0.080 Uiso 0.5 1 calc R . P I 2
C5A' C 1.3288(6) 0.6204(17) -0.0314(5) 0.093(4) Uani 0.5 1 d . U P I 2
H5AE H 1.3512 0.6202 -0.0681 0.139 Uiso 0.5 1 calc GR . P I 2
H5AF H 1.3589 0.5796 -0.0032 0.139 Uiso 0.5 1 calc GR . P I 2
H5AG H 1.3180 0.7162 -0.0208 0.139 Uiso 0.5 1 calc GR . P I 2
C7A' C 1.3216(6) 0.5976(17) 0.1658(6) 0.096(4) Uani 0.5 1 d . U P H 2
H7AD H 1.3172 0.6795 0.1416 0.144 Uiso 0.5 1 calc GR . P H 2
H7AE H 1.3563 0.5356 0.1507 0.144 Uiso 0.5 1 calc GR . P H 2
H7AF H 1.3343 0.6271 0.2038 0.144 Uiso 0.5 1 calc GR . P H 2
C8A' C 1.2477(14) 0.455(3) 0.2215(9) 0.118(12) Uani 0.5 1 d D U P H 2
H8AD H 1.2403 0.5251 0.2507 0.177 Uiso 0.5 1 calc GR . P H 2
H8AE H 1.2882 0.4011 0.2303 0.177 Uiso 0.5 1 calc GR . P H 2
H8AF H 1.2087 0.3927 0.2197 0.177 Uiso 0.5 1 calc GR . P H 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1" C1B 1.835(12) . ?
Cl1B C1B 1.809(11) . ?
N1B C1B 1.334(13) . ?
N1B C2B 1.388(13) . ?
N2B C2B 1.333(12) . ?
N2B C3B 1.357(12) . ?
N3B C1B 1.292(13) . ?
N3B C3B 1.346(12) . ?
N4B H4B 0.8800 . ?
N4B C2B 1.310(12) . ?
N4B C4B 1.504(17) . ?
N4B C4B' 1.52(2) . ?
N5B H5B 0.8800 . ?
N5B C3B 1.324(12) . ?
N5B C6B 1.492(13) . ?
C4B H4BA 0.9900 . ?
C4B H4BB 0.9900 . ?
C4B C5B 1.49(3) . ?
C5B H5BA 0.9800 . ?
C5B H5BB 0.9800 . ?
C5B H5BC 0.9800 . ?
C6B H6B 1.0000 . ?
C6B C7B 1.528(19) . ?
C6B C8B 1.526(16) . ?
C7B H7BA 0.9800 . ?
C7B H7BB 0.9800 . ?
C7B H7BC 0.9800 . ?
C8B H8BA 0.9800 . ?
C8B H8BB 0.9800 . ?
C8B H8BC 0.9800 . ?
C4B' H4BC 0.9900 . ?
C4B' H4BD 0.9900 . ?
C4B' C5B' 1.50(3) . ?
C5B' H5BD 0.9800 . ?
C5B' H5BE 0.9800 . ?
C5B' H5BF 0.9800 . ?
Cl1A C1A 1.762(9) . ?
N1A C1A 1.300(12) . ?
N1A C2A 1.358(12) . ?
N2A C2A 1.321(11) . ?
N2A C3A 1.335(11) . ?
N3A C1A 1.320(12) . ?
N3A C3A 1.368(12) . ?
N4A H4A 0.8800 . ?
N4A H4AA 0.8800 . ?
N4A C2A 1.339(12) . ?
N4A C4A 1.502(14) . ?
N4A C6A' 1.502(14) . ?
N5A H5A 0.8800 . ?
N5A H5AA 0.8800 . ?
N5A C3A 1.322(12) . ?
N5A C6A 1.476(13) . ?
N5A C4A' 1.476(13) . ?
C4A H4AB 0.9900 . ?
C4A H4AC 0.9900 . ?
C4A C5A 1.483(15) . ?
C6A' C7A' 1.483(15) . ?
C6A' C8A' 1.438(17) . ?
C5A H5AB 0.9800 . ?
C5A H5AC 0.9800 . ?
C5A H5AD 0.9800 . ?
C6A H6A 1.0000 . ?
C6A C7A 1.505(17) . ?
C6A C8A 1.40(2) . ?
C7A H7AA 0.9800 . ?
C7A H7AB 0.9800 . ?
C7A H7AC 0.9800 . ?
C8A H8AA 0.9800 . ?
C8A H8AB 0.9800 . ?
C8A H8AC 0.9800 . ?
C4A' H4AD 0.9900 . ?
C4A' H4AE 0.9900 . ?
C4A' C5A' 1.505(17) . ?
C5A' H5AE 0.9800 . ?
C5A' H5AF 0.9800 . ?
C5A' H5AG 0.9800 . ?
C7A' H7AD 0.9801 . ?
C7A' H7AE 0.9800 . ?
C7A' H7AF 0.9800 . ?
C8A' H8AD 0.9800 . ?
C8A' H8AE 0.9800 . ?
C8A' H8AF 0.9800 . ?

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
C1B N1B C2B 110.5(8) . . ?
C2B N2B C3B 115.2(8) . . ?
C1B N3B C3B 112.8(9) . . ?
C2B N4B H4B 119.5 . . ?
C2B N4B C4B 120.9(14) . . ?
C2B N4B C4B' 120(2) . . ?
C4B N4B H4B 119.5 . . ?
C3B N5B H5B 118.3 . . ?
C3B N5B C6B 123.4(9) . . ?
C6B N5B H5B 118.3 . . ?
N1B C1B Cl1" 108.9(8) . . ?
N1B C1B Cl1B 114.4(8) . . ?
N3B C1B Cl1" 117.2(8) . . ?
N3B C1B Cl1B 112.2(8) . . ?
N3B C1B N1B 131.5(9) . . ?
N2B C2B N1B 125.0(9) . . ?
N4B C2B N1B 114.8(9) . . ?
N4B C2B N2B 120.1(9) . . ?
N3B C3B N2B 124.9(9) . . ?
N5B C3B N2B 119.0(8) . . ?
N5B C3B N3B 116.0(9) . . ?
N4B C4B H4BA 110.2 . . ?
N4B C4B H4BB 110.2 . . ?
H4BA C4B H4BB 108.5 . . ?
C5B C4B N4B 107.4(18) . . ?
C5B C4B H4BA 110.2 . . ?
C5B C4B H4BB 110.2 . . ?
C4B C5B H5BA 109.5 . . ?
C4B C5B H5BB 109.5 . . ?
C4B C5B H5BC 109.5 . . ?
H5BA C5B H5BB 109.5 . . ?
H5BA C5B H5BC 109.5 . . ?
H5BB C5B H5BC 109.5 . . ?
N5B C6B H6B 109.1 . . ?
N5B C6B C7B 107.0(11) . . ?
N5B C6B C8B 109.6(9) . . ?
C7B C6B H6B 109.1 . . ?
C8B C6B H6B 109.1 . . ?
C8B C6B C7B 112.8(11) . . ?
C6B C7B H7BA 109.5 . . ?
C6B C7B H7BB 109.5 . . ?
C6B C7B H7BC 109.5 . . ?
H7BA C7B H7BB 109.5 . . ?
H7BA C7B H7BC 109.5 . . ?
H7BB C7B H7BC 109.5 . . ?
C6B C8B H8BA 109.5 . . ?
C6B C8B H8BB 109.5 . . ?
C6B C8B H8BC 109.5 . . ?
H8BA C8B H8BB 109.5 . . ?
H8BA C8B H8BC 109.5 . . ?
H8BB C8B H8BC 109.5 . . ?
N4B C4B' H4BC 108.5 . . ?
N4B C4B' H4BD 108.5 . . ?
H4BC C4B' H4BD 107.5 . . ?
C5B' C4B' N4B 115(3) . . ?
C5B' C4B' H4BC 108.5 . . ?
C5B' C4B' H4BD 108.5 . . ?
C4B' C5B' H5BD 109.5 . . ?
C4B' C5B' H5BE 109.5 . . ?
C4B' C5B' H5BF 109.5 . . ?
H5BD C5B' H5BE 109.5 . . ?
H5BD C5B' H5BF 109.5 . . ?
H5BE C5B' H5BF 109.5 . . ?
C1A N1A C2A 110.8(8) . . ?
C2A N2A C3A 114.0(8) . . ?
C1A N3A C3A 111.4(8) . . ?
C2A N4A H4A 118.0 . . ?
C2A N4A H4AA 118.0 . . ?
C2A N4A C4A 124.0(8) . . ?
C2A N4A C6A' 124.0(8) . . ?
C4A N4A H4A 118.0 . . ?
C6A' N4A H4AA 118.0 . . ?
C3A N5A H5A 117.4 . . ?
C3A N5A H5AA 117.4 . . ?
C3A N5A C6A 125.1(8) . . ?
C3A N5A C4A' 125.1(8) . . ?
C6A N5A H5A 117.4 . . ?
C4A' N5A H5AA 117.4 . . ?
N1A C1A Cl1A 116.5(8) . . ?
N1A C1A N3A 131.2(8) . . ?
N3A C1A Cl1A 112.3(8) . . ?
N2A C2A N1A 127.3(8) . . ?
N2A C2A N4A 118.2(9) . . ?
N4A C2A N1A 114.5(9) . . ?
N2A C3A N3A 125.3(9) . . ?
N5A C3A N2A 117.6(9) . . ?
N5A C3A N3A 117.1(9) . . ?
N4A C4A H4AB 109.4 . . ?
N4A C4A H4AC 109.4 . . ?
H4AB C4A H4AC 108.0 . . ?
C5A C4A N4A 111.4(10) . . ?
C5A C4A H4AB 109.4 . . ?
C5A C4A H4AC 109.4 . . ?
C7A' C6A' N4A 111.4(10) . . ?
C8A' C6A' N4A 106.8(12) . . ?
C8A' C6A' C7A' 110.8(15) . . ?
C4A C5A H5AB 109.5 . . ?
C4A C5A H5AC 109.5 . . ?
C4A C5A H5AD 109.5 . . ?
H5AB C5A H5AC 109.5 . . ?
H5AB C5A H5AD 109.5 . . ?
H5AC C5A H5AD 109.5 . . ?
N5A C6A H6A 109.8 . . ?
N5A C6A C7A 109.6(11) . . ?
C7A C6A H6A 109.8 . . ?
C8A C6A N5A 109.6(13) . . ?
C8A C6A H6A 109.8 . . ?
C8A C6A C7A 108.3(14) . . ?
C6A C7A H7AA 109.5 . . ?
C6A C7A H7AB 109.5 . . ?
C6A C7A H7AC 109.5 . . ?
H7AA C7A H7AB 109.5 . . ?
H7AA C7A H7AC 109.5 . . ?
H7AB C7A H7AC 109.5 . . ?
C6A C8A H8AA 109.5 . . ?
C6A C8A H8AB 109.5 . . ?
C6A C8A H8AC 109.5 . . ?
H8AA C8A H8AB 109.5 . . ?
H8AA C8A H8AC 109.5 . . ?
H8AB C8A H8AC 109.5 . . ?
N5A C4A' H4AD 109.8 . . ?
N5A C4A' H4AE 109.8 . . ?
N5A C4A' C5A' 109.6(11) . . ?
H4AD C4A' H4AE 108.2 . . ?
C5A' C4A' H4AD 109.8 . . ?
C5A' C4A' H4AE 109.8 . . ?
C4A' C5A' H5AE 109.5 . . ?
C4A' C5A' H5AF 109.5 . . ?
C4A' C5A' H5AG 109.5 . . ?
H5AE C5A' H5AF 109.5 . . ?
H5AE C5A' H5AG 109.5 . . ?
H5AF C5A' H5AG 109.5 . . ?
C6A' C7A' H7AD 109.5 . . ?
C6A' C7A' H7AE 109.5 . . ?
C6A' C7A' H7AF 109.5 . . ?
H7AD C7A' H7AE 109.5 . . ?
H7AD C7A' H7AF 109.5 . . ?
H7AE C7A' H7AF 109.5 . . ?
C6A' C8A' H8AD 109.5 . . ?
C6A' C8A' H8AE 109.5 . . ?
C6A' C8A' H8AF 109.5 . . ?
H8AD C8A' H8AE 109.5 . . ?
H8AD C8A' H8AF 109.5 . . ?
H8AE C8A' H8AF 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N4B H4B N3A 0.88 2.14 2.999(11) 165.0 7_576
N5B H5B N1A 0.88 2.18 3.055(11) 174.7 .
N4A H4AA N3B 0.88 2.16 3.039(11) 174.4 .
N5A H5AA N1B 0.88 2.18 3.058(11) 174.5 7_575
C8A H8AB N1B 0.98 2.38 3.24(3) 146.7 2_764
C8A' H8AE N3B 0.98 2.33 3.29(3) 167.7 8_855

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
C1B N1B C2B N2B -1(2) . . . . ?
C1B N1B C2B N4B 175.3(13) . . . . ?
C1B N3B C3B N2B -2(2) . . . . ?
C1B N3B C3B N5B -179.9(13) . . . . ?
C2B N1B C1B Cl1" -160.7(10) . . . . ?
C2B N1B C1B Cl1B 163.8(10) . . . . ?
C2B N1B C1B N3B 1(3) . . . . ?
C2B N2B C3B N3B 2(2) . . . . ?
C2B N2B C3B N5B 179.5(12) . . . . ?
C2B N4B C4B C5B -87(2) . . . . ?
C2B N4B C4B' C5B' -142(4) . . . . ?
C3B N2B C2B N1B 0(2) . . . . ?
C3B N2B C2B N4B -176.4(12) . . . . ?
C3B N3B C1B Cl1" 161.1(11) . . . . ?
C3B N3B C1B Cl1B -162.4(11) . . . . ?
C3B N3B C1B N1B 1(3) . . . . ?
C3B N5B C6B C7B 90.8(14) . . . . ?
C3B N5B C6B C8B -146.6(13) . . . . ?
C4B N4B C2B N1B -171.9(15) . . . . ?
C4B N4B C2B N2B 5(2) . . . . ?
C6B N5B C3B N2B -2.4(19) . . . . ?
C6B N5B C3B N3B 175.3(12) . . . . ?
C4B' N4B C2B N1B 161(2) . . . . ?
C4B' N4B C2B N2B -23(3) . . . . ?
C1A N1A C2A N2A 1.7(15) . . . . ?
C1A N1A C2A N4A -178.2(9) . . . . ?
C1A N3A C3A N2A -0.5(14) . . . . ?
C1A N3A C3A N5A 179.4(9) . . . . ?
C2A N1A C1A Cl1A -179.4(7) . . . . ?
C2A N1A C1A N3A -0.1(15) . . . . ?
C2A N2A C3A N3A 1.8(14) . . . . ?
C2A N2A C3A N5A -178.1(10) . . . . ?
C2A N4A C4A C5A 83.4(13) . . . . ?
C2A N4A C6A' C7A' 83.4(13) . . . . ?
C2A N4A C6A' C8A' -155.5(17) . . . . ?
C3A N2A C2A N1A -2.5(14) . . . . ?
C3A N2A C2A N4A 177.5(10) . . . . ?
C3A N3A C1A Cl1A 178.9(7) . . . . ?
C3A N3A C1A N1A -0.4(15) . . . . ?
C3A N5A C6A C7A -86.9(13) . . . . ?
C3A N5A C6A C8A 154.4(16) . . . . ?
C3A N5A C4A' C5A' -86.9(13) . . . . ?
C4A N4A C2A N1A 177.1(10) . . . . ?
C4A N4A C2A N2A -2.8(16) . . . . ?
C6A' N4A C2A N1A 177.1(10) . . . . ?
C6A' N4A C2A N2A -2.8(16) . . . . ?
C6A N5A C3A N2A 1.9(16) . . . . ?
C6A N5A C3A N3A -178.0(10) . . . . ?
C4A' N5A C3A N2A 1.9(16) . . . . ?
C4A' N5A C3A N3A -178.0(10) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_atraziene_tce_a
_database_code_depnum_ccdc_archive 'CCDC 1435452'
_audit_update_record             
;
2015-11-06 deposited with the CCDC.
2016-01-04 downloaded from the CCDC.
;
_audit_creation_date             2015-09-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C8 H14 Cl N5), 2(C2 H2 Cl4)'
_chemical_formula_sum            'C20 H32 Cl10 N10'
_chemical_formula_weight         767.05
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   11.908(3)
_cell_length_b                   19.374(7)
_cell_length_c                   15.441(5)
_cell_angle_alpha                90
_cell_angle_beta                 105.86(2)
_cell_angle_gamma                90
_cell_volume                     3426.7(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    956
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      18.106
_cell_measurement_theta_min      2.510
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.843
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5336
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1397 before and 0.0831 after correction.
The Ratio of minimum to maximum transmission is 0.7158.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.298
_exptl_crystal_size_mid          0.135
_exptl_crystal_size_min          0.035
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.2258
_diffrn_reflns_av_unetI/netI     0.2638
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            29241
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.140
_diffrn_reflns_theta_min         2.754
_diffrn_ambient_temperature      150.6
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2371
_reflns_number_total             7506
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         2.225
_refine_diff_density_min         -0.498
_refine_diff_density_rms         0.116
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     421
_refine_ls_number_reflns         7506
_refine_ls_number_restraints     79
_refine_ls_R_factor_all          0.2937
_refine_ls_R_factor_gt           0.1058
_refine_ls_restrained_S_all      0.994
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1698P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2634
_refine_ls_wR_factor_ref         0.3773
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Sof: Cl2D(0.5) Cl3D(0.5) Cl1D(0.5) Cl4D(0.5) C1D(0.5) H1D(0.5) C2D(0.5)
 H2D(0.5) Cl0A(0.5) Cl3A(0.5) Cl3(0.5) Cl2(0.5) C2(0.5) H2(0.5) C8(0.5) H8(0.5)
 Fixed Uiso: H4B(0.046) H5B(0.049) H4BA(0.057) H4BB(0.057) H6B(0.051)
 H7BA(0.077) H7BB(0.077) H7BC(0.077) H8BA(0.088) H8BB(0.088) H8BC(0.088)
 H5BA(0.194) H5BB(0.194) H5BC(0.194) H4A(0.052) H5A(0.048) H4AA(0.065)
 H4AB(0.065) H5AA(0.102) H5AB(0.102) H5AC(0.102) H6A(0.072) H7AA(0.12)
 H7AB(0.12) H7AC(0.12) H8AA(0.099) H8AB(0.099) H8AC(0.099) H1C(0.079)
 H2C(0.062) H1D(0.092) H2D(0.073) H2(0.056) H8(0.1)
 Fixed X: H4B(1.1133) H5B(0.6018) H4BA(1.1217) H4BB(0.9834) H6B(0.686)
 H7BA(0.5074) H7BB(0.4507) H7BC(0.4831) H8BA(0.7193) H8BB(0.6234) H8BC(0.584)
 H5BA(0.9592) H5BB(1.0174) H5BC(1.0969) H4A(0.6313) H5A(0.1279) H4AA(0.6542)
 H4AB(0.519) H5AA(0.6257) H5AB(0.564) H5AC(0.6993) H6A(0.2577) H7AA(0.0748)
 H7AB(0.0117) H7AC(0.0863) H8AA(0.1429) H8AB(0.28) H8AC(0.1918) H1C(1.2672)
 H2C(1.1296) H1D(0.618) H2D(0.8196) H2(0.6354) H8(0.8147)
 Fixed Y: H4B(0.6761) H5B(0.6738) H4BA(0.5582) H4BB(0.5541) H6B(0.5885)
 H7BA(0.6406) H7BB(0.611) H7BC(0.5597) H8BA(0.5256) H8BB(0.4885) H8BC(0.5307)
 H5BA(0.6137) H5BB(0.5392) H5BC(0.607) H4A(0.6956) H5A(0.6848) H4AA(0.5845)
 H4AB(0.5727) H5AA(0.5166) H5AB(0.5809) H5AC(0.5848) H6A(0.5676) H7AA(0.5741)
 H7AB(0.5701) H7AC(0.5059) H8AA(0.584) H8AB(0.5737) H8AC(0.5115) H1C(0.6412)
 H2C(0.7268) H1D(0.8375) H2D(0.8612) H2(0.8139) H8(0.8284)
 Fixed Z: H4B(0.4247) H5B(0.4125) H4BA(0.3997) H4BB(0.3851) H6B(0.302)
 H7BA(0.2343) H7BB(0.3094) H7BC(0.2387) H8BA(0.4333) H8BB(0.3538) H8BC(0.4297)
 H5BA(0.2482) H5BB(0.2492) H5BC(0.262) H4A(-0.0297) H5A(-0.015) H4AA(-0.05)
 H4AB(-0.0573) H5AA(0.0675) H5AB(0.1008) H5AC(0.1039) H6A(-0.0249) H7AA(-
 0.1324) H7AB(-0.0533) H7AC(-0.0722) H8AA(0.1114) H8AB(0.1253) H8AC(0.088)
 H1C(0.6346) H2C(0.6191) H1D(0.0932) H2D(0.1505) H2(0.1067) H8(0.1641)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
Cl1B Cl 0.90059(18) 0.84049(14) 0.55797(19) 0.0507(8) Uani 1 1 d . . . . .
N1B N 0.9750(6) 0.7401(4) 0.4777(5) 0.037(2) Uani 1 1 d . . . . .
N2B N 0.8532(5) 0.6468(4) 0.4035(5) 0.035(2) Uani 1 1 d . . . . .
N3B N 0.7751(6) 0.7383(4) 0.4743(5) 0.038(2) Uani 1 1 d . . . . .
N4B N 1.0483(6) 0.6520(4) 0.4124(5) 0.038(2) Uani 1 1 d . . . . .
H4B H 1.1133 0.6761 0.4247 0.046 Uiso 1 1 calc R . . . .
N5B N 0.6588(6) 0.6528(4) 0.3967(5) 0.041(2) Uani 1 1 d . . . . .
H5B H 0.6018 0.6738 0.4125 0.049 Uiso 1 1 calc R . . . .
C1B C 0.8820(7) 0.7652(5) 0.4973(6) 0.033(2) Uani 1 1 d . . . . .
C2B C 0.9549(7) 0.6789(5) 0.4301(6) 0.035(2) Uani 1 1 d . . . . .
C3B C 0.7643(7) 0.6785(6) 0.4265(7) 0.042(3) Uani 1 1 d . . . . .
C4B C 1.0467(8) 0.5818(5) 0.3720(7) 0.048(3) Uani 1 1 d . . . . .
H4BA H 1.1217 0.5582 0.3997 0.057 Uiso 1 1 calc R . . A 2
H4BB H 0.9834 0.5541 0.3851 0.057 Uiso 1 1 calc R . . A 2
C6B C 0.6291(7) 0.5917(6) 0.3390(6) 0.043(3) Uani 1 1 d . . . . .
H6B H 0.6860 0.5885 0.3020 0.051 Uiso 1 1 calc R . . . .
C7B C 0.5065(7) 0.6017(6) 0.2745(7) 0.051(3) Uani 1 1 d . . . . .
H7BA H 0.5074 0.6406 0.2343 0.077 Uiso 1 1 calc GR . . . .
H7BB H 0.4507 0.6110 0.3094 0.077 Uiso 1 1 calc GR . . . .
H7BC H 0.4831 0.5597 0.2387 0.077 Uiso 1 1 calc GR . . . .
C8B C 0.6398(9) 0.5289(6) 0.3935(8) 0.059(3) Uani 1 1 d . . . . .
H8BA H 0.7193 0.5256 0.4333 0.088 Uiso 1 1 calc GR . . . .
H8BB H 0.6234 0.4885 0.3538 0.088 Uiso 1 1 calc GR . . . .
H8BC H 0.5840 0.5307 0.4297 0.088 Uiso 1 1 calc GR . . . .
C5B C 1.0286(16) 0.5857(8) 0.2749(10) 0.129(7) Uani 1 1 d . . . B 2
H5BA H 0.9592 0.6137 0.2482 0.194 Uiso 1 1 calc GR . . B 2
H5BB H 1.0174 0.5392 0.2492 0.194 Uiso 1 1 calc GR . . B 2
H5BC H 1.0969 0.6070 0.2620 0.194 Uiso 1 1 calc GR . . B 2
Cl1A Cl 0.36768(18) 0.88789(13) -0.02352(18) 0.0456(7) Uani 1 1 d . . . . .
N1A N 0.4744(5) 0.7715(4) -0.0248(5) 0.0351(19) Uani 1 1 d . . . . .
N2A N 0.3853(6) 0.6611(4) -0.0126(5) 0.042(2) Uani 1 1 d . . . . .
N3A N 0.2774(5) 0.7678(4) -0.0182(5) 0.0296(18) Uani 1 1 d . . . . .
N4A N 0.5730(6) 0.6695(4) -0.0246(6) 0.043(2) Uani 1 1 d . . . . .
H4A H 0.6313 0.6956 -0.0297 0.052 Uiso 1 1 calc R . . . .
N5A N 0.1922(6) 0.6616(4) -0.0125(5) 0.040(2) Uani 1 1 d . . . . .
H5A H 0.1279 0.6848 -0.0150 0.048 Uiso 1 1 calc R . . . .
C1A C 0.3741(7) 0.7976(5) -0.0226(6) 0.034(2) Uani 1 1 d . . . . .
C2A C 0.4751(7) 0.7018(5) -0.0202(6) 0.031(2) Uani 1 1 d . . . . .
C3A C 0.2892(7) 0.6975(5) -0.0145(6) 0.033(2) Uani 1 1 d . . . . .
C4A C 0.5913(8) 0.5955(5) -0.0215(8) 0.054(3) Uani 1 1 d . . . . .
H4AA H 0.6542 0.5845 -0.0500 0.065 Uiso 1 1 calc R . . . .
H4AB H 0.5190 0.5727 -0.0573 0.065 Uiso 1 1 calc R . . . .
C5A C 0.6227(9) 0.5670(6) 0.0703(9) 0.068(4) Uani 1 1 d . . . . .
H5AA H 0.6257 0.5166 0.0675 0.102 Uiso 1 1 calc GR . . . .
H5AB H 0.5640 0.5809 0.1008 0.102 Uiso 1 1 calc GR . . . .
H5AC H 0.6993 0.5848 0.1039 0.102 Uiso 1 1 calc GR . . . .
C6A C 0.1890(9) 0.5856(6) -0.0065(8) 0.060(3) Uani 1 1 d . . . . .
H6A H 0.2577 0.5676 -0.0249 0.072 Uiso 1 1 calc R . . . .
C7A C 0.0809(10) 0.5563(7) -0.0718(9) 0.080(4) Uani 1 1 d . . . . .
H7AA H 0.0748 0.5741 -0.1324 0.120 Uiso 1 1 calc GR . . . .
H7AB H 0.0117 0.5701 -0.0533 0.120 Uiso 1 1 calc GR . . . .
H7AC H 0.0863 0.5059 -0.0722 0.120 Uiso 1 1 calc GR . . . .
C8A C 0.2021(10) 0.5616(6) 0.0876(8) 0.066(3) Uani 1 1 d . . . . .
H8AA H 0.1429 0.5840 0.1114 0.099 Uiso 1 1 calc GR . . . .
H8AB H 0.2800 0.5737 0.1253 0.099 Uiso 1 1 calc GR . . . .
H8AC H 0.1918 0.5115 0.0880 0.099 Uiso 1 1 calc GR . . . .
Cl1C Cl 1.0903(4) 0.5853(2) 0.6237(3) 0.1098(15) Uani 1 1 d . . . . .
Cl2C Cl 1.2914(3) 0.6039(2) 0.7785(2) 0.0793(11) Uani 1 1 d . . . . .
Cl3C Cl 1.0738(3) 0.71552(18) 0.7496(2) 0.0748(10) Uani 1 1 d . . . . .
Cl4C Cl 1.2903(3) 0.76548(19) 0.7226(2) 0.0769(11) Uani 1 1 d . . . . .
C1C C 1.2143(10) 0.6404(6) 0.6750(7) 0.066(4) Uani 1 1 d . . . . .
H1C H 1.2672 0.6412 0.6346 0.079 Uiso 1 1 calc R . . . .
C2C C 1.1719(8) 0.7111(6) 0.6811(7) 0.051(3) Uani 1 1 d . . . . .
H2C H 1.1296 0.7268 0.6191 0.062 Uiso 1 1 calc R . . . .
Cl2D Cl 0.7392(9) 0.7351(5) 0.2100(9) 0.066(3) Uani 0.5 1 d D U P C 1
Cl3D Cl 0.8202(17) 0.8802(7) 0.3045(11) 0.087(4) Uani 0.5 1 d D U P C 1
Cl1D Cl 0.5534(13) 0.8197(8) 0.2176(14) 0.106(5) Uani 0.5 1 d D U P C 1
Cl4D Cl 0.6708(18) 0.9476(9) 0.1490(17) 0.145(8) Uani 0.5 1 d D U P C 1
C1D C 0.6512(16) 0.8600(12) 0.1531(17) 0.077(6) Uani 0.5 1 d D U P D -21
H1D H 0.6180 0.8375 0.0932 0.092 Uiso 0.5 1 calc R . P D -21
C2D C 0.7607(17) 0.8703(9) 0.1845(12) 0.061(5) Uani 0.5 1 d D U P C 1
H2D H 0.8196 0.8612 0.1505 0.073 Uiso 0.5 1 calc R . P C 1
Cl0A Cl 0.8267(15) 0.8493(9) 0.3045(10) 0.109(5) Uani 0.5 1 d D U P D -21
Cl3A Cl 0.5502(15) 0.8579(9) 0.2159(16) 0.131(7) Uani 0.5 1 d D U P D -21
Cl3 Cl 0.7098(18) 0.9453(10) 0.1387(13) 0.130(6) Uani 0.5 1 d D U P D -21
Cl2 Cl 0.7063(19) 0.7347(11) 0.1997(16) 0.190(9) Uani 0.5 1 d D U P D -21
C2 C 0.6697(14) 0.8184(8) 0.1732(15) 0.047(4) Uani 0.5 1 d D U P C 1
H2 H 0.6354 0.8139 0.1067 0.056 Uiso 0.5 1 calc R . P C 1
C8 C 0.7583(19) 0.8257(10) 0.2016(13) 0.083(5) Uani 0.5 1 d D U P D -21
H8 H 0.8147 0.8284 0.1641 0.100 Uiso 0.5 1 calc R . P D -21


_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
Cl1B C1B 1.715(9) . ?
N1B C1B 1.317(9) . ?
N1B C2B 1.380(12) . ?
N2B C2B 1.323(11) . ?
N2B C3B 1.352(11) . ?
N3B C1B 1.331(10) . ?
N3B C3B 1.361(12) . ?
N4B H4B 0.8800 . ?
N4B C2B 1.323(10) . ?
N4B C4B 1.494(12) . ?
N5B H5B 0.8800 . ?
N5B C3B 1.312(11) . ?
N5B C6B 1.466(12) . ?
C4B H4BA 0.9900 . ?
C4B H4BB 0.9900 . ?
C4B C5B 1.457(17) . ?
C6B H6B 1.0000 . ?
C6B C7B 1.539(13) . ?
C6B C8B 1.464(14) . ?
C7B H7BA 0.9800 . ?
C7B H7BB 0.9800 . ?
C7B H7BC 0.9800 . ?
C8B H8BA 0.9800 . ?
C8B H8BB 0.9800 . ?
C8B H8BC 0.9800 . ?
C5B H5BA 0.9800 . ?
C5B H5BB 0.9800 . ?
C5B H5BC 0.9800 . ?
Cl1A C1A 1.752(10) . ?
N1A C1A 1.306(10) . ?
N1A C2A 1.352(11) . ?
N2A C2A 1.360(10) . ?
N2A C3A 1.337(11) . ?
N3A C1A 1.306(10) . ?
N3A C3A 1.369(11) . ?
N4A H4A 0.8800 . ?
N4A C2A 1.340(10) . ?
N4A C4A 1.449(12) . ?
N5A H5A 0.8800 . ?
N5A C3A 1.355(10) . ?
N5A C6A 1.477(13) . ?
C4A H4AA 0.9900 . ?
C4A H4AB 0.9900 . ?
C4A C5A 1.471(15) . ?
C5A H5AA 0.9800 . ?
C5A H5AB 0.9800 . ?
C5A H5AC 0.9800 . ?
C6A H6A 1.0000 . ?
C6A C7A 1.512(16) . ?
C6A C8A 1.493(16) . ?
C7A H7AA 0.9800 . ?
C7A H7AB 0.9800 . ?
C7A H7AC 0.9800 . ?
C8A H8AA 0.9800 . ?
C8A H8AB 0.9800 . ?
C8A H8AC 0.9800 . ?
Cl1C C1C 1.820(13) . ?
Cl2C C1C 1.760(11) . ?
Cl3C C2C 1.779(11) . ?
Cl4C C2C 1.737(11) . ?
C1C H1C 1.0000 . ?
C1C C2C 1.471(15) . ?
C2C H2C 1.0000 . ?
Cl2D C2 1.832(15) . ?
Cl3D C2D 1.80(3) . ?
Cl1D C2 1.70(2) . ?
Cl4D C2D 1.835(16) . ?
C1D H1D 1.0000 . ?
C1D Cl3A 1.74(3) . ?
C1D Cl3 1.832(17) . ?
C1D C8 1.45(2) . ?
C2D H2D 1.0000 . ?
C2D C2 1.45(2) . ?
Cl0A C8 1.64(2) . ?
Cl2 C8 1.867(17) . ?
C2 H2 1.0000 . ?
C8 H8 1.0000 . ?

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
C1B N1B C2B 113.9(7) . . ?
C2B N2B C3B 114.9(8) . . ?
C1B N3B C3B 114.8(7) . . ?
C2B N4B H4B 119.0 . . ?
C2B N4B C4B 122.0(8) . . ?
C4B N4B H4B 119.0 . . ?
C3B N5B H5B 117.7 . . ?
C3B N5B C6B 124.6(8) . . ?
C6B N5B H5B 117.7 . . ?
N1B C1B Cl1B 116.6(7) . . ?
N1B C1B N3B 126.6(8) . . ?
N3B C1B Cl1B 116.7(6) . . ?
N2B C2B N1B 125.4(7) . . ?
N2B C2B N4B 120.0(9) . . ?
N4B C2B N1B 114.6(8) . . ?
N2B C3B N3B 124.3(8) . . ?
N5B C3B N2B 118.7(9) . . ?
N5B C3B N3B 116.9(8) . . ?
N4B C4B H4BA 109.4 . . ?
N4B C4B H4BB 109.4 . . ?
H4BA C4B H4BB 108.0 . . ?
C5B C4B N4B 111.3(10) . . ?
C5B C4B H4BA 109.4 . . ?
C5B C4B H4BB 109.4 . . ?
N5B C6B H6B 108.0 . . ?
N5B C6B C7B 108.7(8) . . ?
C7B C6B H6B 108.0 . . ?
C8B C6B N5B 110.7(9) . . ?
C8B C6B H6B 108.0 . . ?
C8B C6B C7B 113.2(8) . . ?
C6B C7B H7BA 109.5 . . ?
C6B C7B H7BB 109.5 . . ?
C6B C7B H7BC 109.5 . . ?
H7BA C7B H7BB 109.5 . . ?
H7BA C7B H7BC 109.5 . . ?
H7BB C7B H7BC 109.5 . . ?
C6B C8B H8BA 109.5 . . ?
C6B C8B H8BB 109.5 . . ?
C6B C8B H8BC 109.5 . . ?
H8BA C8B H8BB 109.5 . . ?
H8BA C8B H8BC 109.5 . . ?
H8BB C8B H8BC 109.5 . . ?
C4B C5B H5BA 109.5 . . ?
C4B C5B H5BB 109.5 . . ?
C4B C5B H5BC 109.5 . . ?
H5BA C5B H5BB 109.5 . . ?
H5BA C5B H5BC 109.5 . . ?
H5BB C5B H5BC 109.5 . . ?
C1A N1A C2A 112.2(7) . . ?
C3A N2A C2A 112.5(9) . . ?
C1A N3A C3A 111.1(7) . . ?
C2A N4A H4A 117.1 . . ?
C2A N4A C4A 125.8(8) . . ?
C4A N4A H4A 117.1 . . ?
C3A N5A H5A 118.3 . . ?
C3A N5A C6A 123.4(8) . . ?
C6A N5A H5A 118.3 . . ?
N1A C1A Cl1A 115.1(7) . . ?
N3A C1A Cl1A 113.9(7) . . ?
N3A C1A N1A 131.0(9) . . ?
N1A C2A N2A 126.1(8) . . ?
N4A C2A N1A 117.2(7) . . ?
N4A C2A N2A 116.7(9) . . ?
N2A C3A N3A 127.0(8) . . ?
N2A C3A N5A 117.3(9) . . ?
N5A C3A N3A 115.7(7) . . ?
N4A C4A H4AA 108.9 . . ?
N4A C4A H4AB 108.9 . . ?
N4A C4A C5A 113.4(10) . . ?
H4AA C4A H4AB 107.7 . . ?
C5A C4A H4AA 108.9 . . ?
C5A C4A H4AB 108.9 . . ?
C4A C5A H5AA 109.5 . . ?
C4A C5A H5AB 109.5 . . ?
C4A C5A H5AC 109.5 . . ?
H5AA C5A H5AB 109.5 . . ?
H5AA C5A H5AC 109.5 . . ?
H5AB C5A H5AC 109.5 . . ?
N5A C6A H6A 107.0 . . ?
N5A C6A C7A 111.4(10) . . ?
N5A C6A C8A 111.9(10) . . ?
C7A C6A H6A 107.0 . . ?
C8A C6A H6A 107.0 . . ?
C8A C6A C7A 112.1(9) . . ?
C6A C7A H7AA 109.5 . . ?
C6A C7A H7AB 109.5 . . ?
C6A C7A H7AC 109.5 . . ?
H7AA C7A H7AB 109.5 . . ?
H7AA C7A H7AC 109.5 . . ?
H7AB C7A H7AC 109.5 . . ?
C6A C8A H8AA 109.5 . . ?
C6A C8A H8AB 109.5 . . ?
C6A C8A H8AC 109.5 . . ?
H8AA C8A H8AB 109.5 . . ?
H8AA C8A H8AC 109.5 . . ?
H8AB C8A H8AC 109.5 . . ?
Cl1C C1C H1C 108.2 . . ?
Cl2C C1C Cl1C 108.6(6) . . ?
Cl2C C1C H1C 108.2 . . ?
C2C C1C Cl1C 108.8(8) . . ?
C2C C1C Cl2C 114.7(8) . . ?
C2C C1C H1C 108.2 . . ?
Cl3C C2C H2C 108.3 . . ?
Cl4C C2C Cl3C 110.5(6) . . ?
Cl4C C2C H2C 108.3 . . ?
C1C C2C Cl3C 112.1(8) . . ?
C1C C2C Cl4C 109.3(8) . . ?
C1C C2C H2C 108.3 . . ?
Cl3A C1D H1D 110.3 . . ?
Cl3A C1D Cl3 115.7(17) . . ?
Cl3 C1D H1D 110.3 . . ?
C8 C1D H1D 110.3 . . ?
C8 C1D Cl3A 110.2(17) . . ?
C8 C1D Cl3 99.4(14) . . ?
Cl3D C2D Cl4D 104.7(14) . . ?
Cl3D C2D H2D 115.0 . . ?
Cl4D C2D H2D 115.0 . . ?
C2 C2D Cl3D 105.5(15) . . ?
C2 C2D Cl4D 100.0(13) . . ?
C2 C2D H2D 115.0 . . ?
Cl2D C2 H2 105.4 . . ?
Cl1D C2 Cl2D 103.6(11) . . ?
Cl1D C2 H2 105.4 . . ?
C2D C2 Cl2D 108.3(12) . . ?
C2D C2 Cl1D 127.1(16) . . ?
C2D C2 H2 105.4 . . ?
C1D C8 Cl0A 120.4(17) . . ?
C1D C8 Cl2 100.5(15) . . ?
C1D C8 H8 108.2 . . ?
Cl0A C8 Cl2 110.7(15) . . ?
Cl0A C8 H8 108.2 . . ?
Cl2 C8 H8 108.2 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N4B H4B N3A 0.88 2.20 3.068(10) 169.4 4_676
N5B H5B N1A 0.88 2.27 3.145(10) 171.0 4_576
N4A H4A N3B 0.88 2.13 3.002(10) 173.1 4_575
N5A H5A N1B 0.88 2.31 3.183(10) 171.6 4_475

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
C1B N1B C2B N2B 1.3(14) . . . . ?
C1B N1B C2B N4B -178.0(8) . . . . ?
C1B N3B C3B N2B 0.6(14) . . . . ?
C1B N3B C3B N5B -175.2(8) . . . . ?
C2B N1B C1B Cl1B 179.0(7) . . . . ?
C2B N1B C1B N3B -1.6(14) . . . . ?
C2B N2B C3B N3B -0.8(14) . . . . ?
C2B N2B C3B N5B 174.9(9) . . . . ?
C2B N4B C4B C5B 97.5(12) . . . . ?
C3B N2B C2B N1B -0.2(14) . . . . ?
C3B N2B C2B N4B 179.0(8) . . . . ?
C3B N3B C1B Cl1B -179.8(7) . . . . ?
C3B N3B C1B N1B 0.7(14) . . . . ?
C3B N5B C6B C7B -146.0(9) . . . . ?
C3B N5B C6B C8B 89.1(11) . . . . ?
C4B N4B C2B N1B 172.1(8) . . . . ?
C4B N4B C2B N2B -7.2(14) . . . . ?
C6B N5B C3B N2B -0.4(15) . . . . ?
C6B N5B C3B N3B 175.6(9) . . . . ?
C1A N1A C2A N2A -1.0(13) . . . . ?
C1A N1A C2A N4A 178.2(8) . . . . ?
C1A N3A C3A N2A 1.9(13) . . . . ?
C1A N3A C3A N5A -178.1(8) . . . . ?
C2A N1A C1A Cl1A 177.5(6) . . . . ?
C2A N1A C1A N3A -1.3(14) . . . . ?
C2A N2A C3A N3A -3.6(13) . . . . ?
C2A N2A C3A N5A 176.3(8) . . . . ?
C2A N4A C4A C5A -81.4(12) . . . . ?
C3A N2A C2A N1A 3.2(13) . . . . ?
C3A N2A C2A N4A -176.0(8) . . . . ?
C3A N3A C1A Cl1A -177.8(6) . . . . ?
C3A N3A C1A N1A 0.9(14) . . . . ?
C3A N5A C6A C7A -135.2(9) . . . . ?
C3A N5A C6A C8A 98.3(10) . . . . ?
C4A N4A C2A N1A -179.5(9) . . . . ?
C4A N4A C2A N2A -0.2(14) . . . . ?
C6A N5A C3A N2A 1.4(14) . . . . ?
C6A N5A C3A N3A -178.7(9) . . . . ?
Cl1C C1C C2C Cl3C 61.3(9) . . . . ?
Cl1C C1C C2C Cl4C -175.8(5) . . . . ?
Cl2C C1C C2C Cl3C -60.5(10) . . . . ?
Cl2C C1C C2C Cl4C 62.3(10) . . . . ?
Cl3D C2D C2 Cl2D -69.1(15) . . . . ?
Cl3D C2D C2 Cl1D 55(2) . . . . ?
Cl4D C2D C2 Cl2D -177.6(14) . . . . ?
Cl4D C2D C2 Cl1D -53(2) . . . . ?
Cl3A C1D C8 Cl0A -54(2) . . . . ?
Cl3A C1D C8 Cl2 67.5(19) . . . . ?
Cl3 C1D C8 Cl0A 68(2) . . . . ?
Cl3 C1D C8 Cl2 -170.5(15) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
