# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_CuCl2Hdatrz
_database_code_depnum_ccdc_archive 'CCDC 2209556'
loop_
_audit_author_name
_audit_author_address
'Heesun Park'
;Sogang University
South Korea
;
_audit_update_record             
;
2022-09-26 deposited with the CCDC.	2022-11-14 downloaded from the CCDC.
;

_audit_creation_date             2022-09-14T09:50:43-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C4 H12 Cl2 Cu N10, 2(Cl2 Cu)'
_chemical_formula_sum            'C4 H12 Cl6 Cu3 N10'
_chemical_formula_weight         603.56

#----------------------------------------------------------------------------#
#                   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                   3.71660(10)
_cell_length_b                   7.2862(3)
_cell_length_c                   15.1680(5)
_cell_angle_alpha                84.5650(10)
_cell_angle_beta                 84.9840(10)
_cell_angle_gamma                85.1940(10)
_cell_volume                     406.15(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7421
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      28.38
_cell_measurement_wavelength     0.71076

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

_exptl_crystal_description       needle
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.134
_exptl_crystal_size_mid          0.054
_exptl_crystal_size_min          0.007
_exptl_crystal_density_diffrn    2.468
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             295

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

_exptl_absorpt_coefficient_mu    4.889
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        SADABS-2016/2 - Bruker AXS area detector scaling and absorption correcti
;
_exptl_absorpt_correction_T_min  0.627
_exptl_absorpt_correction_T_max  0.746

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

_diffrn_source                   'sealed x-ray tube'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector                 'PHOTON II CPAD detector'
_diffrn_orient_matrix_type       'x-axis to radiation source'
_diffrn_orient_matrix_ub_11      0.169738
_diffrn_orient_matrix_ub_12      -0.002251
_diffrn_orient_matrix_ub_13      -0.054872
_diffrn_orient_matrix_ub_21      -0.022842
_diffrn_orient_matrix_ub_22      0.138209
_diffrn_orient_matrix_ub_23      -0.007614
_diffrn_orient_matrix_ub_31      0.209874
_diffrn_orient_matrix_ub_32      0.003276
_diffrn_orient_matrix_ub_33      0.036678
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_number            16905
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.016
_diffrn_reflns_theta_max         28.435
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_reflns_Friedel_coverage         0
_reflns_number_total             2036
_reflns_number_gt                1871
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'Bruker APEX4 software'
_computing_cell_refinement       'SAINT V8.40B integration software'
_computing_data_reduction        'Bruker APEX4 software'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

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

_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   direct
_atom_sites_solution_hydrogens   geom

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

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0279P)²+1.9265P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2036
_refine_ls_number_parameters     106
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0435
_refine_ls_wR_factor_ref         0.0973
_refine_ls_wR_factor_gt          0.0954
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_restrained_S_all      1.101
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.135
_refine_diff_density_min         -1.848
_refine_diff_density_rms         0.12

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 '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
C1 C 0.4646(10) 0.2222(5) 0.6624(2) 0.0188(7) Uani 1 1 d . . . . .
C2 C 0.2645(10) 0.0246(5) 0.7715(2) 0.0218(7) Uani 1 1 d . . . . .
Cu1 Cu 0.5 0 0.5 0.01716(15) Uani 1 2 d S . P . .
Cu2 Cu 0.7865(3) 0.46621(12) 0.92901(5) 0.0666(3) Uani 1 1 d . . . . .
N1 N 0.4146(9) 0.0717(4) 0.62505(19) 0.0188(6) Uani 1 1 d . . . . .
N2 N 0.2905(9) -0.0514(4) 0.69502(19) 0.0208(6) Uani 1 1 d . . . . .
H2 H 0.237734 -0.162091 0.689232 0.025 Uiso 1 1 calc R U . . .
N3 N 0.3782(9) 0.1969(4) 0.7527(2) 0.0225(6) Uani 1 1 d . . . . .
H3 H 0.393599 0.27634 0.790371 0.027 Uiso 1 1 calc R U . . .
N4 N 0.5767(10) 0.3800(5) 0.6228(2) 0.0306(8) Uani 1 1 d . . . . .
H4A H 0.625488 0.391633 0.566123 0.037 Uiso 1 1 calc R U . . .
H4B H 0.600399 0.470625 0.653702 0.037 Uiso 1 1 calc R U . . .
N5 N 0.1434(12) -0.0481(5) 0.8497(2) 0.0377(9) Uani 1 1 d . . . . .
H5A H 0.069124 -0.157611 0.855238 0.045 Uiso 1 1 calc R U . . .
H5B H 0.138163 0.013583 0.895447 0.045 Uiso 1 1 calc R U . . .
Cl1 Cl 0.0836(2) 0.23333(11) 0.45341(5) 0.01922(18) Uani 1 1 d . . . . .
Cl2 Cl 0.8558(3) 0.57870(15) 0.78651(7) 0.0347(2) Uani 1 1 d . . . . .
Cl3 Cl 0.3138(3) 0.27393(14) 0.97445(7) 0.0297(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
C1 N1 1.315(4) . ?
C1 N4 1.328(5) . ?
C1 N3 1.377(4) . ?
C2 N5 1.310(5) . ?
C2 N2 1.325(4) . ?
C2 N3 1.355(5) . ?
Cu1 N1 2.007(3) 2_656 ?
Cu1 N1 2.007(3) . ?
Cu1 Cl1 2.3037(8) 2_656 ?
Cu1 Cl1 2.3037(8) . ?
Cu2 Cl2 2.2389(13) . ?
Cu2 Cl3 2.3541(13) . ?
Cu2 Cl3 2.4232(14) 1_655 ?
Cu2 Cl3 2.4859(13) 2_667 ?
Cu2 Cu2 2.8856(18) 2_767 ?
Cu2 Cu2 2.9393(18) 2_667 ?
N1 N2 1.395(4) . ?
N2 H2 0.86 . ?
N3 H3 0.86 . ?
N4 H4A 0.86 . ?
N4 H4B 0.86 . ?
N5 H5A 0.86 . ?
N5 H5B 0.86 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 N4 127.5(3) . . ?
N1 C1 N3 110.0(3) . . ?
N4 C1 N3 122.4(3) . . ?
N5 C2 N2 127.5(4) . . ?
N5 C2 N3 126.3(3) . . ?
N2 C2 N3 106.2(3) . . ?
N1 Cu1 N1 180 2_656 . ?
N1 Cu1 Cl1 90.49(9) 2_656 2_656 ?
N1 Cu1 Cl1 89.51(9) . 2_656 ?
N1 Cu1 Cl1 89.51(9) 2_656 . ?
N1 Cu1 Cl1 90.49(9) . . ?
Cl1 Cu1 Cl1 180 2_656 . ?
Cl2 Cu2 Cl3 118.98(5) . . ?
Cl2 Cu2 Cl3 112.13(5) . 1_655 ?
Cl3 Cu2 Cl3 102.14(5) . 1_655 ?
Cl2 Cu2 Cl3 109.57(5) . 2_667 ?
Cl3 Cu2 Cl3 105.27(4) . 2_667 ?
Cl3 Cu2 Cl3 108.01(5) 1_655 2_667 ?
Cl2 Cu2 Cu2 127.22(6) . 2_767 ?
Cl3 Cu2 Cu2 113.79(5) . 2_767 ?
Cl3 Cu2 Cu2 55.01(4) 1_655 2_767 ?
Cl3 Cu2 Cu2 53.00(4) 2_667 2_767 ?
Cl2 Cu2 Cu2 132.17(7) . 2_667 ?
Cl3 Cu2 Cu2 54.67(4) . 2_667 ?
Cl3 Cu2 Cu2 115.46(5) 1_655 2_667 ?
Cl3 Cu2 Cu2 50.59(4) 2_667 2_667 ?
Cu2 Cu2 Cu2 79.29(4) 2_767 2_667 ?
C1 N1 N2 104.8(3) . . ?
C1 N1 Cu1 133.3(3) . . ?
N2 N1 Cu1 121.9(2) . . ?
C2 N2 N1 111.1(3) . . ?
C2 N2 H2 124.4 . . ?
N1 N2 H2 124.4 . . ?
C2 N3 C1 107.9(3) . . ?
C2 N3 H3 126.1 . . ?
C1 N3 H3 126.1 . . ?
C1 N4 H4A 120 . . ?
C1 N4 H4B 120 . . ?
H4A N4 H4B 120 . . ?
C2 N5 H5A 120 . . ?
C2 N5 H5B 120 . . ?
H5A N5 H5B 120 . . ?
Cu2 Cl3 Cu2 102.14(5) . 1_455 ?
Cu2 Cl3 Cu2 74.73(4) . 2_667 ?
Cu2 Cl3 Cu2 71.99(5) 1_455 2_667 ?

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
_geom_hbond_publ_flag
N2 H2 Cl1 0.86 2.67 3.191(3) 119.9 2_556 yes
N2 H2 Cl2 0.86 2.7 3.381(3) 136.5 1_445 yes
N3 H3 Cl2 0.86 2.9 3.523(3) 131 . yes
N3 H3 Cl3 0.86 2.78 3.447(3) 135.5 . yes
N4 H4A Cl1 0.86 2.59 3.260(4) 136 1_655 yes
N4 H4B Cl1 0.86 2.85 3.254(3) 111 2_666 yes
N4 H4B Cl2 0.86 2.52 3.275(4) 147.3 . yes
N5 H5A Cl2 0.86 2.49 3.258(4) 149.5 1_445 yes
N5 H5A Cl3 0.86 2.93 3.399(4) 116.6 2_557 yes
N5 H5B Cl3 0.86 2.5 3.285(4) 152.6 . yes



# END of CIF
####################################################################### 
# 
# 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_H2datrzCl2
_database_code_depnum_ccdc_archive 'CCDC 2209557'
loop_
_audit_author_name
_audit_author_address
'Heesun Park'
;Sogang University
South Korea
;
_audit_update_record             
;
2022-09-26 deposited with the CCDC.	2022-11-14 downloaded from the CCDC.
;

_audit_creation_date             2022-09-23T17:23:10-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C2 H7 N5, 2(Cl)'
_chemical_formula_sum            'C2 H7 Cl2 N5'
_chemical_formula_weight         172.03

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_Int_Tables_number      61
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   14.0559(3)
_cell_length_b                   7.0932(2)
_cell_length_c                   14.1687(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1412.64(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    9890
_cell_measurement_theta_min      2.88
_cell_measurement_theta_max      28.34
_cell_measurement_wavelength     0.71076

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

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.135
_exptl_crystal_size_min          0.002
_exptl_crystal_density_diffrn    1.618
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704

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

_exptl_absorpt_coefficient_mu    0.839
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        SADABS-2016/2 - Bruker AXS area detector scaling and absorption correcti
;
_exptl_absorpt_correction_T_min  0.682
_exptl_absorpt_correction_T_max  0.746

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

_diffrn_source                   'sealed x-ray tube'
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector                 'PHOTON II CPAD detector'
_diffrn_orient_matrix_type       'x-axis to radiation source'
_diffrn_orient_matrix_ub_11      -0.136752
_diffrn_orient_matrix_ub_12      -0.006585
_diffrn_orient_matrix_ub_13      -0.015873
_diffrn_orient_matrix_ub_21      -0.027529
_diffrn_orient_matrix_ub_22      0.060298
_diffrn_orient_matrix_ub_23      0.034854
_diffrn_orient_matrix_ub_31      0.020406
_diffrn_orient_matrix_ub_32      0.03718
_diffrn_orient_matrix_ub_33      -0.059284
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_av_unetI/netI     0.0122
_diffrn_reflns_number            48171
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.875
_diffrn_reflns_theta_max         28.366
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_reflns_Friedel_coverage         0
_reflns_number_total             1769
_reflns_number_gt                1525
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'Bruker APEX4 software'
_computing_cell_refinement       'SAINT V8.40B integration software'
_computing_data_reduction        'Bruker APEX4 software'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

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

_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   direct
_atom_sites_solution_hydrogens   geom

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

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0271P)²+1.3395P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1769
_refine_ls_number_parameters     82
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0366
_refine_ls_wR_factor_ref         0.0846
_refine_ls_wR_factor_gt          0.0809
_refine_ls_goodness_of_fit_ref   1.15
_refine_ls_restrained_S_all      1.15
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.055

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   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'
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
N1 N 0.46883(11) 0.6316(3) 0.41151(12) 0.0311(4) Uani 1 1 d . . . . .
H1 H 0.527593 0.643159 0.427373 0.037 Uiso 1 1 calc R U . . .
N2 N 0.43576(12) 0.5584(3) 0.32739(12) 0.0330(4) Uani 1 1 d . . . . .
H2 H 0.470342 0.520478 0.281059 0.04 Uiso 1 1 calc R U . . .
N3 N 0.31531(11) 0.6303(2) 0.41493(11) 0.0261(3) Uani 1 1 d . . . . .
H3 H 0.2578 0.642979 0.434642 0.031 Uiso 1 1 calc R U . . .
N4 N 0.39644(13) 0.7585(3) 0.54682(13) 0.0397(4) Uani 1 1 d . . . . .
H4A H 0.449865 0.783244 0.573696 0.048 Uiso 1 1 calc R U . . .
H4B H 0.343902 0.785167 0.574927 0.048 Uiso 1 1 calc R U . . .
N5 N 0.28355(13) 0.4961(3) 0.26497(13) 0.0413(5) Uani 1 1 d . . . . .
H5A H 0.305791 0.451028 0.213129 0.05 Uiso 1 1 calc R U . . .
H5B H 0.223077 0.501276 0.273845 0.05 Uiso 1 1 calc R U . . .
C1 C 0.39509(13) 0.6805(3) 0.46332(14) 0.0272(4) Uani 1 1 d . . . . .
C2 C 0.34169(14) 0.5568(3) 0.33034(14) 0.0281(4) Uani 1 1 d . . . . .
Cl1 Cl 0.67132(3) 0.76073(8) 0.42503(4) 0.03639(15) Uani 1 1 d . . . . .
Cl2 Cl 0.57393(4) 0.56491(8) 0.16507(4) 0.03738(15) 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
N1 C1 1.317(2) . ?
N1 N2 1.380(2) . ?
N1 H1 0.86 . ?
N2 C2 1.323(3) . ?
N2 H2 0.86 . ?
N3 C2 1.359(2) . ?
N3 C1 1.362(2) . ?
N3 H3 0.86 . ?
N4 C1 1.306(3) . ?
N4 H4A 0.86 . ?
N4 H4B 0.86 . ?
N5 C2 1.308(3) . ?
N5 H5A 0.86 . ?
N5 H5B 0.86 . ?

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 N2 108.39(16) . . ?
C1 N1 H1 125.8 . . ?
N2 N1 H1 125.8 . . ?
C2 N2 N1 108.21(16) . . ?
C2 N2 H2 125.9 . . ?
N1 N2 H2 125.9 . . ?
C2 N3 C1 108.64(16) . . ?
C2 N3 H3 125.7 . . ?
C1 N3 H3 125.7 . . ?
C1 N4 H4A 120 . . ?
C1 N4 H4B 120 . . ?
H4A N4 H4B 120 . . ?
C2 N5 H5A 120 . . ?
C2 N5 H5B 120 . . ?
H5A N5 H5B 120 . . ?
N4 C1 N1 127.25(19) . . ?
N4 C1 N3 125.36(18) . . ?
N1 C1 N3 107.37(17) . . ?
N5 C2 N2 127.22(19) . . ?
N5 C2 N3 125.48(18) . . ?
N2 C2 N3 107.30(17) . . ?

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
_geom_hbond_publ_flag
N1 H1 Cl1 0.86 2.19 2.9962(17) 157 . yes
N2 H2 Cl2 0.86 2.22 3.0105(17) 153.1 . yes
N3 H3 Cl1 0.86 2.43 3.1362(16) 140 4_466 yes
N4 H4A Cl2 0.86 2.42 3.2556(19) 162.8 7_576 yes
N4 H4B Cl1 0.86 2.45 3.1922(19) 145.3 4_466 yes
N5 H5A Cl1 0.86 2.4 3.231(2) 162.7 3_645 yes
N5 H5B Cl2 0.86 2.31 3.147(2) 163.5 6_556 yes



# END of CIF
