# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_Cu_90k
_database_code_depnum_ccdc_archive 'CCDC 1561506'
_audit_update_record             
;
2017-07-16 deposited with the CCDC.
2017-11-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H10 Cl2 Cu N2 O'
_chemical_formula_sum            'C9 H10 Cl2 Cu N2 O'
_chemical_formula_weight         296.63

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'
Cu Cu 0.3201 1.2651 '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'

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

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.7231(3)
_cell_length_b                   7.7113(3)
_cell_length_c                   14.1209(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.440(4)
_cell_angle_gamma                90
_cell_volume                     1037.72(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    2647
_cell_measurement_theta_min      4.7490
_cell_measurement_theta_max      29.2760

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.899
_exptl_crystal_F_000             596
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.900
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    2.589
_shelx_estimated_absorpt_T_min   0.204
_shelx_estimated_absorpt_T_max   0.625
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.867
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_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.
;
_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova (Mo) X-ray Source'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 5.2913
_diffrn_reflns_number            4778
_diffrn_reflns_av_unetI/netI     0.0426
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.399
_diffrn_reflns_theta_max         29.679
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.843
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.843
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.843
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2475
_reflns_number_gt                2243
_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-2014/7 (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)+(0.0223P)²+0.6503P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2475
_refine_ls_number_parameters     176
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0340
_refine_ls_R_factor_gt           0.0302
_refine_ls_wR_factor_ref         0.0682
_refine_ls_wR_factor_gt          0.0654
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_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
Cu1 Cu 0.68741(3) 0.42570(3) 0.81527(2) 0.00837(9) Uani 1 1 d . . . . .
Cl1 Cl 0.51063(6) 0.53331(8) 0.70294(4) 0.01360(13) Uani 1 1 d . . . . .
Cl2 Cl 0.85395(6) 0.56870(7) 0.75954(4) 0.01167(13) Uani 1 1 d . . . . .
O1 O 0.84742(17) 0.3009(2) 0.90798(12) 0.0091(3) Uani 1 1 d . . . . .
H1 H 0.884(3) 0.240(4) 0.879(2) 0.027(9) Uiso 1 1 d . . . . .
N1 N 0.57960(19) 0.3321(2) 0.90792(13) 0.0070(4) Uani 1 1 d . . . . .
N2 N 0.57936(19) 0.1894(2) 1.04457(13) 0.0083(4) Uani 1 1 d . . . . .
C1 C 0.8061(2) 0.2033(3) 0.98360(17) 0.0097(4) Uani 1 1 d . . . . .
H1A H 0.861(3) 0.237(4) 1.045(2) 0.019(7) Uiso 1 1 d . . . . .
H1B H 0.818(3) 0.086(3) 0.9725(19) 0.012(7) Uiso 1 1 d . . . . .
C2 C 0.6545(2) 0.2418(3) 0.97930(15) 0.0081(4) Uani 1 1 d . . . . .
C3 C 0.4442(2) 0.3397(3) 0.92689(16) 0.0078(4) Uani 1 1 d . . . . .
C4 C 0.3210(2) 0.4154(3) 0.87603(17) 0.0094(5) Uani 1 1 d . . . . .
H4 H 0.321(2) 0.470(3) 0.8217(18) 0.003(6) Uiso 1 1 d . . . . .
C5 C 0.2009(2) 0.3974(3) 0.91360(17) 0.0105(5) Uani 1 1 d . . . . .
H5 H 0.119(3) 0.446(3) 0.8809(19) 0.014(7) Uiso 1 1 d . . . . .
C6 C 0.2026(2) 0.3104(3) 1.00147(17) 0.0113(5) Uani 1 1 d . . . . .
H6 H 0.122(3) 0.305(3) 1.0249(18) 0.013(7) Uiso 1 1 d . . . . .
C7 C 0.3241(2) 0.2362(3) 1.05334(17) 0.0100(4) Uani 1 1 d . . . . .
H7 H 0.327(3) 0.181(3) 1.1146(19) 0.012(6) Uiso 1 1 d . . . . .
C8 C 0.4432(2) 0.2512(3) 1.01349(16) 0.0091(4) Uani 1 1 d . . . . .
C9 C 0.6322(3) 0.1018(3) 1.13662(18) 0.0125(5) Uani 1 1 d . . . . .
H9A H 0.563(3) 0.020(4) 1.149(2) 0.029(8) Uiso 1 1 d . . . . .
H9B H 0.718(4) 0.049(4) 1.136(2) 0.034(9) Uiso 1 1 d . . . . .
H9C H 0.644(3) 0.183(4) 1.190(2) 0.034(9) Uiso 1 1 d . . . . .


_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 N1 1.9685(18) . ?
Cu1 O1 2.0623(16) . ?
Cu1 Cl2 2.2277(6) . ?
Cu1 Cl1 2.2534(6) . ?
O1 C1 1.427(3) . ?
O1 H1 0.75(3) . ?
N1 C2 1.319(3) . ?
N1 C3 1.395(3) . ?
N2 C2 1.347(3) . ?
N2 C8 1.393(3) . ?
N2 C9 1.465(3) . ?
C1 C2 1.493(3) . ?
C1 H1A 0.96(3) . ?
C1 H1B 0.93(3) . ?
C3 C4 1.397(3) . ?
C3 C8 1.402(3) . ?
C4 C5 1.382(3) . ?
C4 H4 0.88(3) . ?
C5 C6 1.408(3) . ?
C5 H5 0.92(3) . ?
C6 C7 1.384(3) . ?
C6 H6 0.91(3) . ?
C7 C8 1.390(3) . ?
C7 H7 0.96(3) . ?
C9 H9A 0.96(3) . ?
C9 H9B 0.92(3) . ?
C9 H9C 0.97(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Cu1 O1 80.86(7) . . ?
N1 Cu1 Cl2 159.46(6) . . ?
O1 Cu1 Cl2 86.88(5) . . ?
N1 Cu1 Cl1 99.81(5) . . ?
O1 Cu1 Cl1 173.14(5) . . ?
Cl2 Cu1 Cl1 94.33(2) . . ?
C1 O1 Cu1 115.60(13) . . ?
C1 O1 H1 108(2) . . ?
Cu1 O1 H1 109(2) . . ?
C2 N1 C3 105.91(18) . . ?
C2 N1 Cu1 114.54(15) . . ?
C3 N1 Cu1 139.39(15) . . ?
C2 N2 C8 106.98(18) . . ?
C2 N2 C9 127.11(19) . . ?
C8 N2 C9 125.56(19) . . ?
O1 C1 C2 106.67(18) . . ?
O1 C1 H1A 110.0(17) . . ?
C2 C1 H1A 110.6(16) . . ?
O1 C1 H1B 109.0(17) . . ?
C2 C1 H1B 109.9(17) . . ?
H1A C1 H1B 111(2) . . ?
N1 C2 N2 112.90(19) . . ?
N1 C2 C1 121.8(2) . . ?
N2 C2 C1 125.3(2) . . ?
N1 C3 C4 131.6(2) . . ?
N1 C3 C8 108.49(18) . . ?
C4 C3 C8 119.9(2) . . ?
C5 C4 C3 117.7(2) . . ?
C5 C4 H4 122.2(16) . . ?
C3 C4 H4 120.1(16) . . ?
C4 C5 C6 121.5(2) . . ?
C4 C5 H5 118.7(17) . . ?
C6 C5 H5 119.7(17) . . ?
C7 C6 C5 121.5(2) . . ?
C7 C6 H6 119.7(16) . . ?
C5 C6 H6 118.8(16) . . ?
C6 C7 C8 116.3(2) . . ?
C6 C7 H7 122.1(16) . . ?
C8 C7 H7 121.5(15) . . ?
C7 C8 N2 131.3(2) . . ?
C7 C8 C3 123.0(2) . . ?
N2 C8 C3 105.70(19) . . ?
N2 C9 H9A 109.6(18) . . ?
N2 C9 H9B 111(2) . . ?
H9A C9 H9B 112(3) . . ?
N2 C9 H9C 110.9(19) . . ?
H9A C9 H9C 105(3) . . ?
H9B C9 H9C 109(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 O1 C1 C2 -7.3(2) . . . . ?
C3 N1 C2 N2 -0.3(2) . . . . ?
Cu1 N1 C2 N2 175.96(14) . . . . ?
C3 N1 C2 C1 179.07(19) . . . . ?
Cu1 N1 C2 C1 -4.7(3) . . . . ?
C8 N2 C2 N1 -0.2(2) . . . . ?
C9 N2 C2 N1 -173.7(2) . . . . ?
C8 N2 C2 C1 -179.6(2) . . . . ?
C9 N2 C2 C1 6.9(4) . . . . ?
O1 C1 C2 N1 7.9(3) . . . . ?
O1 C1 C2 N2 -172.8(2) . . . . ?
C2 N1 C3 C4 -179.0(2) . . . . ?
Cu1 N1 C3 C4 6.3(4) . . . . ?
C2 N1 C3 C8 0.7(2) . . . . ?
Cu1 N1 C3 C8 -174.07(17) . . . . ?
N1 C3 C4 C5 178.9(2) . . . . ?
C8 C3 C4 C5 -0.8(3) . . . . ?
C3 C4 C5 C6 1.8(3) . . . . ?
C4 C5 C6 C7 -1.1(3) . . . . ?
C5 C6 C7 C8 -0.5(3) . . . . ?
C6 C7 C8 N2 -178.2(2) . . . . ?
C6 C7 C8 C3 1.6(3) . . . . ?
C2 N2 C8 C7 -179.5(2) . . . . ?
C9 N2 C8 C7 -5.9(4) . . . . ?
C2 N2 C8 C3 0.6(2) . . . . ?
C9 N2 C8 C3 174.3(2) . . . . ?
N1 C3 C8 C7 179.34(19) . . . . ?
C4 C3 C8 C7 -1.0(3) . . . . ?
N1 C3 C8 N2 -0.8(2) . . . . ?
C4 C3 C8 N2 178.90(19) . . . . ?

_refine_diff_density_max         0.533
_refine_diff_density_min         -0.467
_refine_diff_density_rms         0.096

####################################################################### 
# 
# 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_Cu1_296k
_database_code_depnum_ccdc_archive 'CCDC 1561507'
_audit_update_record             
;
2017-07-16 deposited with the CCDC.
2017-11-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H10 Cl2 Cu N2 O'
_chemical_formula_sum            'C9 H10 Cl2 Cu N2 O'
_chemical_formula_weight         296.63

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'
Cu Cu 0.3201 1.2651 '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'

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

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.752(3)
_cell_length_b                   7.817(2)
_cell_length_c                   14.238(4)
_cell_angle_alpha                90
_cell_angle_beta                 101.212(3)
_cell_angle_gamma                90
_cell_volume                     1064.7(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    16861
_cell_measurement_theta_min      2.328
_cell_measurement_theta_max      30.7475

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.851
_exptl_crystal_F_000             596
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          1.000
_exptl_crystal_size_mid          0.600
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    2.524
_shelx_estimated_absorpt_T_min   0.187
_shelx_estimated_absorpt_T_max   0.632
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1869
_exptl_absorpt_correction_T_max  0.6323
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15478
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.917
_diffrn_reflns_theta_max         30.844
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3171
_reflns_number_gt                2894
_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-2014/7 (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)+(0.0244P)²+0.5908P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3171
_refine_ls_number_parameters     176
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0287
_refine_ls_R_factor_gt           0.0249
_refine_ls_wR_factor_ref         0.0633
_refine_ls_wR_factor_gt          0.0610
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.092
_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
Cu1 Cu 0.68803(2) 0.42261(2) 0.31456(2) 0.02319(6) Uani 1 1 d . . . . .
Cl1 Cl 0.51243(4) 0.52799(7) 0.20328(3) 0.03923(11) Uani 1 1 d . . . . .
Cl2 Cl 0.85428(4) 0.56357(6) 0.25953(3) 0.03267(10) Uani 1 1 d . . . . .
O1 O 0.84744(11) 0.29757(15) 0.40627(8) 0.0244(2) Uani 1 1 d . . . . .
H1 H 0.884(2) 0.230(3) 0.3780(15) 0.035(6) Uiso 1 1 d . . . . .
N1 N 0.58102(12) 0.33091(15) 0.40724(8) 0.0197(2) Uani 1 1 d . . . . .
N2 N 0.58117(13) 0.19279(16) 0.54400(9) 0.0225(2) Uani 1 1 d . . . . .
C1 C 0.80638(16) 0.2041(2) 0.48231(11) 0.0259(3) Uani 1 1 d D . . . .
H1A H 0.820(3) 0.084(2) 0.4739(17) 0.042(6) Uiso 1 1 d D . . . .
H1B H 0.863(2) 0.240(3) 0.5416(13) 0.039(6) Uiso 1 1 d D . . . .
C2 C 0.65598(14) 0.24273(18) 0.47858(10) 0.0205(3) Uani 1 1 d . . . . .
C3 C 0.44621(14) 0.33867(18) 0.42641(10) 0.0192(2) Uani 1 1 d . . . . .
C4 C 0.32321(16) 0.4119(2) 0.37554(11) 0.0252(3) Uani 1 1 d . . . . .
H4 H 0.324(2) 0.469(3) 0.3187(15) 0.027(5) Uiso 1 1 d . . . . .
C5 C 0.20361(16) 0.3942(2) 0.41353(13) 0.0310(3) Uani 1 1 d . . . . .
H5 H 0.124(3) 0.447(3) 0.3811(17) 0.042(6) Uiso 1 1 d . . . . .
C6 C 0.20600(16) 0.3098(2) 0.50076(13) 0.0314(3) Uani 1 1 d . . . . .
H6 H 0.123(3) 0.306(3) 0.5246(17) 0.041(6) Uiso 1 1 d . . . . .
C7 C 0.32680(17) 0.2380(2) 0.55247(12) 0.0280(3) Uani 1 1 d . . . . .
H7 H 0.329(2) 0.182(3) 0.6138(16) 0.038(6) Uiso 1 1 d . . . . .
C8 C 0.44602(15) 0.25254(18) 0.51273(10) 0.0211(3) Uani 1 1 d . . . . .
C9 C 0.6348(2) 0.1078(3) 0.63529(12) 0.0339(4) Uani 1 1 d D . . . .
H9A H 0.641(3) 0.187(3) 0.6876(17) 0.071(9) Uiso 1 1 d D . . . .
H9B H 0.724(2) 0.061(3) 0.636(2) 0.087(11) Uiso 1 1 d D . . . .
H9C H 0.573(3) 0.018(3) 0.650(2) 0.095(11) Uiso 1 1 d D . . . .


_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 N1 1.9697(12) . ?
Cu1 O1 2.0707(12) . ?
Cu1 Cl2 2.2250(6) . ?
Cu1 Cl1 2.2509(6) . ?
O1 C1 1.4266(18) . ?
O1 H1 0.79(2) . ?
N1 C2 1.3239(18) . ?
N1 C3 1.3949(17) . ?
N2 C2 1.3477(18) . ?
N2 C8 1.3875(19) . ?
N2 C9 1.463(2) . ?
C1 C2 1.488(2) . ?
C1 H1A 0.955(15) . ?
C1 H1B 0.956(15) . ?
C3 C4 1.398(2) . ?
C3 C8 1.4017(19) . ?
C4 C5 1.385(2) . ?
C4 H4 0.93(2) . ?
C5 C6 1.403(3) . ?
C5 H5 0.92(2) . ?
C6 C7 1.381(2) . ?
C6 H6 0.93(2) . ?
C7 C8 1.393(2) . ?
C7 H7 0.97(2) . ?
C9 H9A 0.962(15) . ?
C9 H9B 0.942(16) . ?
C9 H9C 0.975(16) . ?

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 Cu1 O1 80.58(5) . . ?
N1 Cu1 Cl2 158.97(4) . . ?
O1 Cu1 Cl2 86.95(4) . . ?
N1 Cu1 Cl1 100.08(4) . . ?
O1 Cu1 Cl1 172.65(4) . . ?
Cl2 Cu1 Cl1 94.45(2) . . ?
C1 O1 Cu1 115.67(9) . . ?
C1 O1 H1 105.6(16) . . ?
Cu1 O1 H1 110.7(16) . . ?
C2 N1 C3 105.86(11) . . ?
C2 N1 Cu1 114.71(10) . . ?
C3 N1 Cu1 139.24(10) . . ?
C2 N2 C8 106.79(12) . . ?
C2 N2 C9 126.71(13) . . ?
C8 N2 C9 126.22(13) . . ?
O1 C1 C2 106.80(12) . . ?
O1 C1 H1A 110.0(15) . . ?
C2 C1 H1A 110.5(15) . . ?
O1 C1 H1B 108.7(14) . . ?
C2 C1 H1B 111.3(14) . . ?
H1A C1 H1B 109(2) . . ?
N1 C2 N2 112.88(13) . . ?
N1 C2 C1 121.76(12) . . ?
N2 C2 C1 125.36(13) . . ?
N1 C3 C4 131.53(13) . . ?
N1 C3 C8 108.22(12) . . ?
C4 C3 C8 120.25(13) . . ?
C5 C4 C3 117.39(15) . . ?
C5 C4 H4 122.5(13) . . ?
C3 C4 H4 120.1(13) . . ?
C4 C5 C6 121.50(15) . . ?
C4 C5 H5 117.0(15) . . ?
C6 C5 H5 121.4(15) . . ?
C7 C6 C5 121.93(15) . . ?
C7 C6 H6 120.1(14) . . ?
C5 C6 H6 117.9(14) . . ?
C6 C7 C8 116.30(15) . . ?
C6 C7 H7 122.0(14) . . ?
C8 C7 H7 121.7(14) . . ?
N2 C8 C7 131.15(14) . . ?
N2 C8 C3 106.25(12) . . ?
C7 C8 C3 122.60(14) . . ?
N2 C9 H9A 110.6(17) . . ?
N2 C9 H9B 111(2) . . ?
H9A C9 H9B 108.5(19) . . ?
N2 C9 H9C 113(2) . . ?
H9A C9 H9C 104.1(19) . . ?
H9B C9 H9C 109(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 O1 C1 C2 -6.42(15) . . . . ?
C3 N1 C2 N2 -0.54(16) . . . . ?
Cu1 N1 C2 N2 175.50(9) . . . . ?
C3 N1 C2 C1 178.71(13) . . . . ?
Cu1 N1 C2 C1 -5.24(18) . . . . ?
C8 N2 C2 N1 0.26(17) . . . . ?
C9 N2 C2 N1 -173.92(15) . . . . ?
C8 N2 C2 C1 -178.96(14) . . . . ?
C9 N2 C2 C1 6.9(2) . . . . ?
O1 C1 C2 N1 7.7(2) . . . . ?
O1 C1 C2 N2 -173.13(14) . . . . ?
C2 N1 C3 C4 -178.63(15) . . . . ?
Cu1 N1 C3 C4 6.9(3) . . . . ?
C2 N1 C3 C8 0.61(15) . . . . ?
Cu1 N1 C3 C8 -173.89(11) . . . . ?
N1 C3 C4 C5 178.67(15) . . . . ?
C8 C3 C4 C5 -0.5(2) . . . . ?
C3 C4 C5 C6 1.5(2) . . . . ?
C4 C5 C6 C7 -0.9(3) . . . . ?
C5 C6 C7 C8 -0.7(2) . . . . ?
C2 N2 C8 C7 -179.88(15) . . . . ?
C9 N2 C8 C7 -5.7(3) . . . . ?
C2 N2 C8 C3 0.13(16) . . . . ?
C9 N2 C8 C3 174.35(15) . . . . ?
C6 C7 C8 N2 -178.34(15) . . . . ?
C6 C7 C8 C3 1.6(2) . . . . ?
N1 C3 C8 N2 -0.46(15) . . . . ?
C4 C3 C8 N2 178.88(13) . . . . ?
N1 C3 C8 C7 179.56(13) . . . . ?
C4 C3 C8 C7 -1.1(2) . . . . ?

_refine_diff_density_max         0.311
_refine_diff_density_min         -0.452
_refine_diff_density_rms         0.077

