# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018

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

data_e1153a
_database_code_depnum_ccdc_archive 'CCDC 1455402'
_audit_update_record             
;
2017-01-30 deposited with the CCDC.
2018-08-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C6 H8 Cl N2), Cl4 Cu, 2(H2 O)'
_chemical_formula_sum            'C12 H20 Cl6 Cu N4 O2'
_chemical_formula_weight         528.56

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   7.1563(6)
_cell_length_b                   8.0445(5)
_cell_length_c                   9.1508(8)
_cell_angle_alpha                94.831(6)
_cell_angle_beta                 90.917(7)
_cell_angle_gamma                91.361(6)
_cell_volume                     524.70(7)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1932
_cell_measurement_theta_min      2.2277
_cell_measurement_theta_max      28.2406

_exptl_crystal_description       plate
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.673
_exptl_crystal_F_000             267
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.516
_exptl_crystal_size_mid          0.417
_exptl_crystal_size_min          0.111
_exptl_absorpt_coefficient_mu    1.819
_shelx_estimated_absorpt_T_min   0.454
_shelx_estimated_absorpt_T_max   0.824
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.464
_exptl_absorpt_correction_T_max  0.817
_exptl_absorpt_process_details   'Oxford Diffraction CrysAlis'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Oxford Sapphire CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.2564
_diffrn_reflns_number            3419
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_av_R_equivalents  0.0167
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.234
_diffrn_reflns_theta_max         28.370
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.885
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.885
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.885
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2329
_reflns_number_gt                1865
_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       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'CIFTAB (Sheldrick, 2014)'

_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)+(0.0500P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     patterson
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2329
_refine_ls_number_parameters     115
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0355
_refine_ls_wR_factor_ref         0.0949
_refine_ls_wR_factor_gt          0.0902
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.5000 0.5000 -0.5000 0.03374(15) Uani 1 2 d S . P . .
Cl1 Cl 0.75888(11) 0.66668(10) -0.49819(8) 0.0546(2) Uani 1 1 d . . . . .
Cl2 Cl 0.49786(11) 0.52489(10) -0.25069(7) 0.0536(2) Uani 1 1 d . . . . .
N1 N 0.1777(3) 0.8022(3) -0.0534(2) 0.0348(5) Uani 1 1 d . . . . .
H1N H 0.1324 0.7237 -0.1228 0.042 Uiso 1 1 d R U . . .
C2 C 0.2311(3) 0.9488(3) -0.0975(3) 0.0348(6) Uani 1 1 d . . . . .
Cl21 Cl 0.23401(11) 0.96871(11) -0.28096(7) 0.0587(2) Uani 1 1 d . . . . .
C3 C 0.2805(3) 1.0834(3) 0.0040(3) 0.0346(6) Uani 1 1 d . . . . .
N31 N 0.3273(4) 1.2353(3) -0.0388(3) 0.0544(7) Uani 1 1 d . . . . .
H1N3 H 0.3820 1.3161 0.0371 0.065 Uiso 1 1 d R U . . .
H2N3 H 0.3407 1.2549 -0.1379 0.065 Uiso 1 1 d R U . . .
C4 C 0.2776(3) 1.0497(3) 0.1506(3) 0.0354(6) Uani 1 1 d . . . . .
H4A H 0.3111 1.1348 0.2220 0.042 Uiso 1 1 calc R U . . .
C5 C 0.2269(3) 0.8948(3) 0.1944(3) 0.0338(5) Uani 1 1 d . . . . .
C51 C 0.2283(5) 0.8625(4) 0.3530(3) 0.0500(7) Uani 1 1 d . . . . .
H51A H 0.2684 0.9621 0.4114 0.060 Uiso 1 1 calc R U . . .
H51B H 0.1046 0.8303 0.3807 0.060 Uiso 1 1 calc R U . . .
H51C H 0.3127 0.7745 0.3688 0.060 Uiso 1 1 calc R U . . .
C6 C 0.1742(4) 0.7709(3) 0.0874(3) 0.0363(6) Uani 1 1 d . . . . .
H6A H 0.1363 0.6661 0.1132 0.044 Uiso 1 1 calc R U . . .
O1W O 0.0298(3) 0.5567(3) -0.2385(2) 0.0505(5) Uani 1 1 d . . . . .
H1W1 H -0.0598 0.5613 -0.2906 0.061 Uiso 1 1 d R U . . .
H2W1 H 0.1149 0.4843 -0.2715 0.061 Uiso 1 1 d R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.0384(3) 0.0283(2) 0.0344(2) 0.00273(18) 0.00192(18) -0.00251(18)
Cl1 0.0563(5) 0.0574(5) 0.0476(4) -0.0049(3) 0.0084(3) -0.0242(4)
Cl2 0.0640(5) 0.0612(5) 0.0350(3) 0.0049(3) 0.0011(3) -0.0159(4)
N1 0.0363(11) 0.0399(12) 0.0271(10) -0.0020(9) -0.0035(9) -0.0031(9)
C2 0.0314(13) 0.0491(16) 0.0248(11) 0.0076(11) 0.0008(10) 0.0015(11)
Cl21 0.0644(5) 0.0881(6) 0.0254(3) 0.0146(3) 0.0022(3) 0.0018(4)
C3 0.0306(13) 0.0376(14) 0.0360(13) 0.0055(11) 0.0042(10) 0.0000(10)
N31 0.0676(17) 0.0441(14) 0.0529(14) 0.0154(12) 0.0041(13) -0.0110(12)
C4 0.0377(14) 0.0385(14) 0.0291(12) -0.0019(11) 0.0009(10) -0.0004(11)
C5 0.0350(13) 0.0406(14) 0.0259(11) 0.0036(11) 0.0006(10) 0.0019(11)
C51 0.066(2) 0.0565(19) 0.0281(12) 0.0076(13) 0.0014(13) 0.0058(15)
C6 0.0425(15) 0.0353(14) 0.0312(12) 0.0058(11) 0.0003(11) -0.0047(11)
O1W 0.0512(12) 0.0570(13) 0.0406(10) -0.0100(9) -0.0021(9) -0.0053(9)

_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
Cu1 Cl1 2.2600(7) 2_664 ?
Cu1 Cl1 2.2600(7) . ?
Cu1 Cl2 2.2736(7) 2_664 ?
Cu1 Cl2 2.2737(7) . ?
N1 C2 1.328(3) . ?
N1 C6 1.334(3) . ?
N1 H1N 0.9071 . ?
C2 C3 1.401(4) . ?
C2 Cl21 1.700(2) . ?
C3 N31 1.350(3) . ?
C3 C4 1.391(3) . ?
N31 H1N3 0.9803 . ?
N31 H2N3 0.9396 . ?
C4 C5 1.383(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.379(4) . ?
C5 C51 1.496(3) . ?
C51 H51A 0.9600 . ?
C51 H51B 0.9600 . ?
C51 H51C 0.9600 . ?
C6 H6A 0.9300 . ?
O1W H1W1 0.7963 . ?
O1W H2W1 0.8912 . ?

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
Cl1 Cu1 Cl1 180.0 2_664 . ?
Cl1 Cu1 Cl2 90.62(3) 2_664 2_664 ?
Cl1 Cu1 Cl2 89.38(3) . 2_664 ?
Cl1 Cu1 Cl2 89.38(3) 2_664 . ?
Cl1 Cu1 Cl2 90.62(3) . . ?
Cl2 Cu1 Cl2 180.00(4) 2_664 . ?
C2 N1 C6 123.1(2) . . ?
C2 N1 H1N 117.4 . . ?
C6 N1 H1N 119.3 . . ?
N1 C2 C3 121.0(2) . . ?
N1 C2 Cl21 117.83(19) . . ?
C3 C2 Cl21 121.1(2) . . ?
N31 C3 C4 122.7(2) . . ?
N31 C3 C2 121.8(2) . . ?
C4 C3 C2 115.5(2) . . ?
C3 N31 H1N3 116.3 . . ?
C3 N31 H2N3 122.4 . . ?
H1N3 N31 H2N3 119.1 . . ?
C5 C4 C3 122.7(2) . . ?
C5 C4 H4A 118.7 . . ?
C3 C4 H4A 118.7 . . ?
C6 C5 C4 117.9(2) . . ?
C6 C5 C51 120.9(2) . . ?
C4 C5 C51 121.1(2) . . ?
C5 C51 H51A 109.5 . . ?
C5 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
C5 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
N1 C6 C5 119.7(2) . . ?
N1 C6 H6A 120.2 . . ?
C5 C6 H6A 120.2 . . ?
H1W1 O1W H2W1 114.9 . . ?

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
C6 N1 C2 C3 -2.6(4) . . . . ?
C6 N1 C2 Cl21 178.37(19) . . . . ?
N1 C2 C3 N31 -177.1(3) . . . . ?
Cl21 C2 C3 N31 1.9(3) . . . . ?
N1 C2 C3 C4 2.8(4) . . . . ?
Cl21 C2 C3 C4 -178.21(19) . . . . ?
N31 C3 C4 C5 179.0(3) . . . . ?
C2 C3 C4 C5 -0.9(4) . . . . ?
C3 C4 C5 C6 -1.2(4) . . . . ?
C3 C4 C5 C51 179.1(3) . . . . ?
C2 N1 C6 C5 0.3(4) . . . . ?
C4 C5 C6 N1 1.6(4) . . . . ?
C51 C5 C6 N1 -178.7(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
N1 H1N O1W 0.91 1.78 2.677(3) 172.1 .
N31 H1N3 Cl2 0.98 2.38 3.350(3) 169.7 2_675
N31 H2N3 Cl2 0.94 2.71 3.374(2) 128.2 1_565
C4 H4A Cl1 0.93 2.93 3.771(3) 151.1 2_675
C6 H6A O1W 0.93 2.50 3.389(3) 161.1 2_565
O1W H1W1 Cl1 0.80 2.50 3.237(2) 154.2 1_455
O1W H2W1 Cl1 0.89 2.53 3.292(2) 143.5 2_664
O1W H2W1 Cl2 0.89 2.75 3.368(2) 127.2 .

_refine_diff_density_max         0.370
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.069

_shelxl_version_number           2014-3

_shelx_res_file                  
;
TITL e1153a in P-1
REM P-1 (#2 in standard setting)
CELL 0.71073   7.156268   8.044546   9.150777  94.8307  90.9170  91.3613
ZERR    1.00   0.000647   0.000492   0.000766   0.0060   0.0071   0.0062
LATT  1
SFAC C H N O Cl Cu
UNIT 12.00 20.00 4.00 2.00 6.00 1.00

TEMP  20
SIZE  0.5159 0.4172 0.1105

L.S. 10
BOND $H
FMAP 2
PLAN 5

OMIT  -3

HTAB
HTAB N1 O1W
EQIV $1 -x+1, -y+2, -z
HTAB N31 Cl2_$1
EQIV $2 x, y+1, z
HTAB N31 Cl2_$2
HTAB C4 Cl1_$1
EQIV $3 -x, -y+1, -z
HTAB C6 O1W_$3
EQIV $4 x-1, y, z
HTAB O1W Cl1_$4
EQIV $5 -x+1, -y+1, -z-1
HTAB O1W Cl1_$5
HTAB O1W Cl2

CONF
ACTA 50

WGHT    0.050010
FVAR       7.63215
CU1   6    0.500000    0.500000   -0.500000    10.50000    0.03845    0.02827 =
         0.03439    0.00273    0.00192   -0.00251
CL1   5    0.758881    0.666683   -0.498194    11.00000    0.05633    0.05739 =
         0.04756   -0.00488    0.00840   -0.02417
CL2   5    0.497856    0.524894   -0.250686    11.00000    0.06402    0.06120 =
         0.03501    0.00490    0.00109   -0.01591
N1    3    0.177680    0.802154   -0.053424    11.00000    0.03632    0.03986 =
         0.02712   -0.00201   -0.00351   -0.00312
AFIX   3
H1N   2    0.132400    0.723714   -0.122835    11.00000   -1.20000
AFIX   0
C2    1    0.231060    0.948817   -0.097483    11.00000    0.03140    0.04906 =
         0.02484    0.00760    0.00079    0.00154
CL21  5    0.234013    0.968710   -0.280958    11.00000    0.06439    0.08807 =
         0.02545    0.01456    0.00221    0.00179
C3    1    0.280454    1.083434    0.004013    11.00000    0.03065    0.03762 =
         0.03601    0.00554    0.00419   -0.00003
N31   3    0.327287    1.235274   -0.038763    11.00000    0.06757    0.04406 =
         0.05294    0.01545    0.00412   -0.01102
AFIX   3
H1N3  2    0.381987    1.316074    0.037117    11.00000   -1.20000
H2N3  2    0.340687    1.254874   -0.137883    11.00000   -1.20000
AFIX   0
C4    1    0.277570    1.049739    0.150589    11.00000    0.03772    0.03854 =
         0.02910   -0.00186    0.00088   -0.00043
AFIX  43
H4A   2    0.311087    1.134825    0.221999    11.00000   -1.20000
AFIX   0
C5    1    0.226879    0.894832    0.194446    11.00000    0.03503    0.04062 =
         0.02592    0.00356    0.00055    0.00185
C51   1    0.228273    0.862542    0.353044    11.00000    0.06630    0.05647 =
         0.02806    0.00762    0.00136    0.00583
AFIX  33
H51A  2    0.268408    0.962120    0.411417    11.00000   -1.20000
H51B  2    0.104648    0.830265    0.380724    11.00000   -1.20000
H51C  2    0.312658    0.774516    0.368789    11.00000   -1.20000
AFIX   0
C6    1    0.174151    0.770945    0.087389    11.00000    0.04253    0.03533 =
         0.03115    0.00580    0.00026   -0.00474
AFIX  43
H6A   2    0.136312    0.666137    0.113231    11.00000   -1.20000
AFIX   0
O1W   4    0.029832    0.556719   -0.238522    11.00000    0.05120    0.05702 =
         0.04057   -0.00996   -0.00214   -0.00526
AFIX   3
H1W1  2   -0.059788    0.561310   -0.290602    11.00000   -1.20000
H2W1  2    0.114912    0.484308   -0.271502    11.00000   -1.20000

AFIX   0
HKLF 4

REM  e1153a in P-1
REM R1 =  0.0355 for    1865 Fo > 4sig(Fo)  and  0.0483 for all    2329 data
REM    115 parameters refined using      0 restraints

END

WGHT      0.0501      0.0000

REM Instructions for potential hydrogen bonds
HTAB N1 O1W
HTAB N31 Cl2_$1
HTAB N31 Cl2_$2
HTAB C4 Cl1_$1
HTAB C6 O1W_$3
HTAB O1W Cl1_$4
HTAB O1W Cl1_$5
HTAB O1W Cl2

REM Highest difference peak  0.370,  deepest hole -0.366,  1-sigma level  0.069
Q1    1   0.3552  0.8711  0.3932  11.00000  0.05    0.37
Q2    1   0.4589  0.6050 -0.2834  11.00000  0.05    0.33
Q3    1   0.7740  0.5691 -0.4883  11.00000  0.05    0.33
Q4    1   0.2176  1.0674 -0.2735  11.00000  0.05    0.30
Q5    1   0.1856  0.7592  0.3621  11.00000  0.05    0.27
;
_shelx_res_checksum              56283

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_e1158a
_database_code_depnum_ccdc_archive 'CCDC 1530155'
_audit_update_record             
;
2017-01-30 deposited with the CCDC.
2018-08-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H16 N2, Cl4 Cu'
_chemical_formula_sum            'C6 H16 Cl4 Cu N2'
_chemical_formula_weight         321.55

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   14.5594(6)
_cell_length_b                   14.5888(5)
_cell_length_c                   5.9318(3)
_cell_angle_alpha                90
_cell_angle_beta                 107.295(5)
_cell_angle_gamma                90
_cell_volume                     1202.97(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2359
_cell_measurement_theta_min      2.0189
_cell_measurement_theta_max      28.3678

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.775
_exptl_crystal_F_000             652
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.551
_exptl_crystal_size_mid          0.273
_exptl_crystal_size_min          0.161
_exptl_absorpt_coefficient_mu    2.663
_shelx_estimated_absorpt_T_min   0.321
_shelx_estimated_absorpt_T_max   0.674
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.440975
_exptl_absorpt_correction_T_max  0.730698
_exptl_absorpt_process_details   'Oxford Diffraction CrysAlis'


_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Oxford Sapphire CCD'
_diffrn_measurement_method       θ/2θ
_diffrn_detector_area_resol_mean 8.2564
_diffrn_reflns_number            3912
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         2.792
_diffrn_reflns_theta_max         28.445
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.912
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.912
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.912
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1382
_reflns_number_gt                1158
_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       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'CIFTAB (Sheldrick, 2014)'

_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)+(0.0354P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0075(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1382
_refine_ls_number_parameters     62
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0279
_refine_ls_R_factor_gt           0.0224
_refine_ls_wR_factor_ref         0.0633
_refine_ls_wR_factor_gt          0.0621
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.0000 0.08854(2) 0.2500 0.02105(13) Uani 1 2 d S T P . .
Cl2 Cl 0.16991(3) 0.08841(3) 0.38078(8) 0.02483(14) Uani 1 1 d . . . . .
Cl3 Cl 0.0000 0.24319(4) 0.2500 0.02799(17) Uani 1 2 d S T P . .
Cl4 Cl 0.0000 -0.06736(4) 0.2500 0.02238(16) Uani 1 2 d S T P . .
N1 N 0.20605(11) 0.16437(10) -0.0918(3) 0.0269(4) Uani 1 1 d . . . . .
H1N1 H 0.1830 0.1264 -0.2129 0.032 Uiso 1 1 calc R U . . .
H2N1 H 0.1984 0.1380 0.0367 0.032 Uiso 1 1 calc R U . . .
C2 C 0.31077(13) 0.18026(13) -0.0572(3) 0.0265(4) Uani 1 1 d . . . . .
H2A H 0.3187 0.2055 -0.2033 0.032 Uiso 1 1 calc R U . . .
C3 C 0.34875(13) 0.24846(13) 0.1382(3) 0.0296(4) Uani 1 1 d . . . . .
H3A H 0.3449 0.2225 0.2856 0.036 Uiso 1 1 calc R U . . .
H3B H 0.4159 0.2608 0.1548 0.036 Uiso 1 1 calc R U . . .
C4 C 0.36575(19) 0.09081(13) -0.0024(5) 0.0494(7) Uani 1 1 d . . . . .
H4A H 0.4328 0.1020 0.0194 0.059 Uiso 1 1 calc R U . . .
H4B H 0.3577 0.0649 0.1393 0.059 Uiso 1 1 calc R U . . .
H4C H 0.3416 0.0488 -0.1311 0.059 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.01702(19) 0.01660(19) 0.0289(2) 0.000 0.00587(13) 0.000
Cl2 0.0194(2) 0.0309(3) 0.0238(2) -0.00126(19) 0.00595(18) -0.00263(16)
Cl3 0.0296(4) 0.0193(3) 0.0374(4) 0.000 0.0136(3) 0.000
Cl4 0.0192(3) 0.0161(3) 0.0307(3) 0.000 0.0057(2) 0.000
N1 0.0247(9) 0.0308(9) 0.0254(8) -0.0078(7) 0.0075(7) -0.0128(6)
C2 0.0234(10) 0.0302(11) 0.0277(10) -0.0043(8) 0.0103(8) -0.0103(7)
C3 0.0222(10) 0.0353(12) 0.0280(10) -0.0030(9) 0.0025(8) -0.0082(8)
C4 0.0409(15) 0.0351(13) 0.0729(18) -0.0044(12) 0.0182(13) -0.0050(9)

_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
Cu1 Cl3 2.2562(7) . ?
Cu1 Cl4 2.2744(6) . ?
Cu1 Cl2 2.3623(5) . ?
Cu1 Cl2 2.3623(5) 2 ?
N1 C3 1.483(2) 7 ?
N1 C2 1.495(2) . ?
N1 H1N1 0.8900 . ?
N1 H2N1 0.8900 . ?
C2 C3 1.503(2) . ?
C2 C4 1.515(3) . ?
C2 H2A 0.9800 . ?
C3 N1 1.483(2) 7 ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 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
Cl3 Cu1 Cl4 180.0 . . ?
Cl3 Cu1 Cl2 90.045(12) . . ?
Cl4 Cu1 Cl2 89.955(12) . . ?
Cl3 Cu1 Cl2 90.046(12) . 2 ?
Cl4 Cu1 Cl2 89.954(12) . 2 ?
Cl2 Cu1 Cl2 179.91(2) . 2 ?
C3 N1 C2 111.29(14) 7 . ?
C3 N1 H1N1 109.4 7 . ?
C2 N1 H1N1 109.4 . . ?
C3 N1 H2N1 109.4 7 . ?
C2 N1 H2N1 109.4 . . ?
H1N1 N1 H2N1 108.0 . . ?
N1 C2 C3 109.58(14) . . ?
N1 C2 C4 110.38(16) . . ?
C3 C2 C4 110.80(18) . . ?
N1 C2 H2A 108.7 . . ?
C3 C2 H2A 108.7 . . ?
C4 C2 H2A 108.7 . . ?
N1 C3 C2 111.74(16) 7 . ?
N1 C3 H3A 109.3 7 . ?
C2 C3 H3A 109.3 . . ?
N1 C3 H3B 109.3 7 . ?
C2 C3 H3B 109.3 . . ?
H3A C3 H3B 107.9 . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 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 N1 C2 C3 55.9(2) 7 . . . ?
C3 N1 C2 C4 178.19(18) 7 . . . ?
N1 C2 C3 N1 -56.2(2) . . . 7 ?
C4 C2 C3 N1 -178.21(17) . . . 7 ?

_refine_diff_density_max         0.284
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.066

_shelxl_version_number           2014-3

_shelx_res_file                  
;
TITL e1158a in C2/c
REM C2/c (#15 in standard setting)
CELL 0.71073  14.559447  14.588783   5.931759  90.0000 107.2947  90.0000
ZERR    4.00   0.000620   0.000531   0.000269   0.0000   0.0046   0.0000
LATT  7
SYMM -x, y,-z+1/2
SFAC C H N Cl Cu
UNIT 24.00 64.00 8.00 16.00 4.00

SIZE  0.5512 0.2733 0.1607
TEMP  20

L.S. 10
BOND  $H
FMAP 2
PLAN 5

ACTA
HTAB
CONF

OMIT  -3
OMIT   1   1   0
OMIT  -1   1   1

WGHT    0.035400
EXTI    0.007538
FVAR       3.74005
CU1   5    0.000000    0.088540    0.250000    10.50000    0.01702    0.01660 =
         0.02889    0.00000    0.00587    0.00000
CL2   4    0.169914    0.088413    0.380782    11.00000    0.01945    0.03090 =
         0.02384   -0.00126    0.00595   -0.00263
CL3   4    0.000000    0.243190    0.250000    10.50000    0.02962    0.01933 =
         0.03739    0.00000    0.01360    0.00000
CL4   4    0.000000   -0.067359    0.250000    10.50000    0.01920    0.01615 =
         0.03065    0.00000    0.00568    0.00000
N1    3    0.206050    0.164370   -0.091821    11.00000    0.02470    0.03075 =
         0.02542   -0.00780    0.00753   -0.01283
AFIX  23
H1N1  2    0.183024    0.126365   -0.212850    11.00000   -1.20000
H2N1  2    0.198388    0.138026    0.036722    11.00000   -1.20000
AFIX   0
C2    1    0.310775    0.180257   -0.057179    11.00000    0.02336    0.03021 =
         0.02772   -0.00434    0.01029   -0.01027
AFIX  13
H2A   2    0.318697    0.205523   -0.203348    11.00000   -1.20000
AFIX   0
C3    1    0.348754    0.248456    0.138203    11.00000    0.02224    0.03531 =
         0.02799   -0.00298    0.00252   -0.00815
AFIX  23
H3A   2    0.344881    0.222481    0.285636    11.00000   -1.20000
H3B   2    0.415910    0.260806    0.154812    11.00000   -1.20000
AFIX   0
C4    1    0.365752    0.090806   -0.002372    11.00000    0.04093    0.03505 =
         0.07295   -0.00445    0.01818   -0.00501
AFIX  33
H4A   2    0.432807    0.102027    0.019417    11.00000   -1.20000
H4B   2    0.357699    0.064856    0.139275    11.00000   -1.20000
H4C   2    0.341592    0.048846   -0.131073    11.00000   -1.20000

AFIX   0
HKLF 4

REM  e1158a in C2/c
REM R1 =  0.0224 for    1158 Fo > 4sig(Fo)  and  0.0279 for all    1382 data
REM     62 parameters refined using      0 restraints

END

WGHT      0.0355      0.0000

REM Instructions for potential hydrogen bonds
EQIV $1 x, y, z-1
HTAB N1 Cl2_$1
EQIV $2 -x, -y, -z
HTAB N1 Cl4_$2
HTAB N1 Cl2
EQIV $3 -x+1/2, -y+1/2, -z
HTAB C2 Cl3_$3
EQIV $4 x+1/2, y+1/2, z
HTAB C3 Cl4_$4

REM Highest difference peak  0.284,  deepest hole -0.371,  1-sigma level  0.066
Q1    1   0.2650  0.1736 -0.0656  11.00000  0.05    0.28
Q2    1   0.3304  0.1416 -0.0225  11.00000  0.05    0.26
Q3    1   0.3231  0.2186  0.0273  11.00000  0.05    0.25
Q4    1   0.3872  0.0937  0.1576  11.00000  0.05    0.24
Q5    1  -0.0048  0.1719  0.1578  11.00000  0.05    0.23
;
_shelx_res_checksum              11332


# Formatted by publCIF
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
