# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 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_1
_audit_block_doi                 10.5517/ccdc.csd.cc1ps0t9
_database_code_depnum_ccdc_archive 'CCDC 1572221'
_audit_update_record             
;
2017-12-06 deposited with the CCDC.
2018-02-05 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         ?
_chemical_formula_sum            'C12 H10 Cl0 Co N2 O4'
_chemical_formula_weight         305.15

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'
Co Co 0.3494 0.9721 '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      tetragonal
_space_group_IT_number           96
_space_group_name_H-M_alt        'P 43 21 2'
_space_group_name_Hall           'P 4nw 2abw'

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

_cell_length_a                   7.9778(4)
_cell_length_b                   7.9778(4)
_cell_length_c                   17.3831(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1106.35(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1786
_cell_measurement_theta_min      2.81
_cell_measurement_theta_max      25.78

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.832
_exptl_crystal_F_000             620
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_exptl_absorpt_coefficient_mu    1.563
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6516
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4695
_diffrn_reflns_av_unetI/netI     0.0520
_diffrn_reflns_av_R_equivalents  0.0492
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.809
_diffrn_reflns_theta_max         26.318
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1117
_reflns_number_gt                951
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.577
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0312P)²+0.0775P] 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 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.02(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1117
_refine_ls_number_parameters     90
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0354
_refine_ls_wR_factor_ref         0.0674
_refine_ls_wR_factor_gt          0.0640
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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
Co1 Co 0.26449(6) 0.26449(6) 0.0000 0.0080(2) Uani 1 2 d S T P . .
O1 O 0.3990(4) 0.1290(3) 0.08730(14) 0.0140(7) Uani 1 1 d . . . . .
O2 O 0.6097(3) 0.0987(3) 0.17108(14) 0.0135(7) Uani 1 1 d . . . . .
N1 N 0.4518(3) 0.4518(3) 0.0000 0.0099(9) Uani 1 2 d S T P . .
N2 N 0.0765(4) 0.0765(4) 0.0000 0.0113(10) Uani 1 2 d S T P . .
C1 C 0.4322(5) 0.5944(5) 0.0406(2) 0.0119(9) Uani 1 1 d . . . . .
H1 H 0.3334 0.6084 0.0704 0.014 Uiso 1 1 calc R U . . .
C2 C 0.5502(5) 0.7208(5) 0.0406(2) 0.0118(9) Uani 1 1 d . . . . .
H2 H 0.5304 0.8220 0.0679 0.014 Uiso 1 1 calc R U . . .
C3 C 0.6980(4) 0.6980(4) 0.0000 0.0132(13) Uani 1 2 d S T P . .
C4 C 0.8297(5) 0.8297(5) 0.0000 0.0111(12) Uani 1 2 d S T P . .
C5 C 0.7876(5) 0.9975(4) -0.0111(2) 0.0121(9) Uani 1 1 d . . . . .
H5 H 0.6742 1.0300 -0.0185 0.014 Uiso 1 1 calc R U . . .
C6 C 0.1148(5) -0.0862(5) 0.0112(2) 0.0121(9) Uani 1 1 d . . . . .
H6 H 0.2289 -0.1152 0.0195 0.015 Uiso 1 1 calc R U . . .
C7 C 0.5292(5) 0.1780(5) 0.12057(19) 0.0115(9) Uani 1 1 d . . . . .
H7 H 0.5711 0.2851 0.1064 0.014 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
Co1 0.0073(3) 0.0073(3) 0.0096(3) 0.0001(2) -0.0001(2) -0.0008(4)
O1 0.0126(17) 0.0138(16) 0.0156(13) -0.0015(13) -0.0075(13) -0.0012(13)
O2 0.0161(17) 0.0129(16) 0.0116(13) 0.0010(12) -0.0046(13) 0.0015(14)
N1 0.0106(14) 0.0106(14) 0.008(2) 0.0013(16) -0.0013(16) -0.0026(18)
N2 0.0112(14) 0.0112(14) 0.012(2) 0.0013(17) -0.0013(17) -0.0027(19)
C1 0.011(2) 0.013(2) 0.0112(19) -0.0005(18) -0.0008(17) 0.0009(17)
C2 0.013(2) 0.009(2) 0.014(2) -0.0032(18) 0.0024(17) -0.0014(17)
C3 0.0130(19) 0.0130(19) 0.014(3) 0.006(2) -0.006(2) -0.003(2)
C4 0.0119(17) 0.0119(17) 0.010(3) -0.0042(19) 0.0042(19) -0.001(2)
C5 0.007(2) 0.014(2) 0.015(2) -0.0013(17) -0.0014(19) -0.0011(16)
C6 0.008(2) 0.012(2) 0.017(2) 0.0002(18) -0.0008(19) 0.0035(15)
C7 0.016(2) 0.009(2) 0.010(2) -0.0004(17) 0.0038(19) 0.0005(17)

_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
Co1 N1 2.113(4) . ?
Co1 N2 2.121(4) . ?
Co1 O2 2.144(3) 2_544 ?
Co1 O2 2.144(2) 5_455 ?
Co1 O1 2.150(3) 6 ?
Co1 O1 2.150(3) . ?
O1 C7 1.251(4) . ?
O2 C7 1.259(4) . ?
O2 Co1 2.144(3) 4 ?
N1 C1 1.348(4) . ?
N1 C1 1.348(4) 6 ?
N2 C6 1.347(4) . ?
N2 C6 1.347(4) 6 ?
C1 C2 1.379(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.386(4) . ?
C2 H2 0.9500 . ?
C3 C2 1.386(4) 6 ?
C3 C4 1.486(7) . ?
C4 C5 1.393(4) 6 ?
C4 C5 1.393(4) . ?
C5 C6 1.375(5) 6_665 ?
C5 H5 0.9500 . ?
C6 C5 1.375(5) 6_445 ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?

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 Co1 N2 180.00(3) . . ?
N1 Co1 O2 92.70(8) . 2_544 ?
N2 Co1 O2 87.30(8) . 2_544 ?
N1 Co1 O2 92.70(8) . 5_455 ?
N2 Co1 O2 87.30(8) . 5_455 ?
O2 Co1 O2 174.60(15) 2_544 5_455 ?
N1 Co1 O1 90.15(8) . 6 ?
N2 Co1 O1 89.85(8) . 6 ?
O2 Co1 O1 95.27(10) 2_544 6 ?
O2 Co1 O1 84.72(10) 5_455 6 ?
N1 Co1 O1 90.15(8) . . ?
N2 Co1 O1 89.85(8) . . ?
O2 Co1 O1 84.72(10) 2_544 . ?
O2 Co1 O1 95.27(10) 5_455 . ?
O1 Co1 O1 179.70(17) 6 . ?
C7 O1 Co1 125.7(3) . . ?
C7 O2 Co1 119.0(3) . 4 ?
C1 N1 C1 118.0(5) . 6 ?
C1 N1 Co1 121.0(2) . . ?
C1 N1 Co1 121.0(2) 6 . ?
C6 N2 C6 117.3(4) . 6 ?
C6 N2 Co1 121.4(2) . . ?
C6 N2 Co1 121.4(2) 6 . ?
N1 C1 C2 122.5(4) . . ?
N1 C1 H1 118.7 . . ?
C2 C1 H1 118.7 . . ?
C1 C2 C3 119.0(4) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C2 C3 C2 118.8(5) . 6 ?
C2 C3 C4 120.6(2) . . ?
C2 C3 C4 120.6(2) 6 . ?
C5 C4 C5 118.8(5) 6 . ?
C5 C4 C3 120.6(2) 6 . ?
C5 C4 C3 120.6(2) . . ?
C6 C5 C4 118.5(4) 6_665 . ?
C6 C5 H5 120.7 6_665 . ?
C4 C5 H5 120.7 . . ?
N2 C6 C5 123.4(4) . 6_445 ?
N2 C6 H6 118.3 . . ?
C5 C6 H6 118.3 6_445 . ?
O1 C7 O2 126.1(4) . . ?
O1 C7 H7 117.0 . . ?
O2 C7 H7 117.0 . . ?

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
C1 N1 C1 C2 1.5(3) 6 . . . ?
Co1 N1 C1 C2 -178.5(3) . . . . ?
N1 C1 C2 C3 -2.9(5) . . . . ?
C1 C2 C3 C2 1.4(2) . . . 6 ?
C1 C2 C3 C4 -178.6(2) . . . . ?
C2 C3 C4 C5 134.5(3) . . . 6 ?
C2 C3 C4 C5 -45.5(3) 6 . . 6 ?
C2 C3 C4 C5 -45.5(3) . . . . ?
C2 C3 C4 C5 134.5(3) 6 . . . ?
C5 C4 C5 C6 0.4(2) 6 . . 6_665 ?
C3 C4 C5 C6 -179.6(2) . . . 6_665 ?
C6 N2 C6 C5 0.5(3) 6 . . 6_445 ?
Co1 N2 C6 C5 -179.5(3) . . . 6_445 ?
Co1 O1 C7 O2 -179.1(3) . . . . ?
Co1 O2 C7 O1 -156.3(3) 4 . . . ?

_refine_diff_density_max         0.367
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.095

_shelx_res_file                  
;

    1.res created by SHELXL-2014/7

TITL 1 in P4(3)2(1)2                  New: P43212
CELL  0.71073    7.9778    7.9778   17.3831    90.000    90.000    90.000
ZERR        4    0.0004    0.0004    0.0015     0.000     0.000     0.000
LATT -1
SYMM     0.50000 - Y ,    0.50000 + X ,    0.75000 + Z
SYMM             - X ,            - Y ,    0.50000 + Z
SYMM     0.50000 + Y ,    0.50000 - X ,    0.25000 + Z
SYMM     0.50000 + X ,    0.50000 - Y ,    0.25000 - Z
SYMM               Y ,              X ,            - Z
SYMM     0.50000 - X ,    0.50000 + Y ,    0.75000 - Z
SYMM             - Y ,            - X ,    0.50000 - Z
SFAC C  H  Cl Co N  O
UNIT 48 40 0 4 8 16
L.S. 15
ACTA
BOND $H
FMAP 2
PLAN 0
WGHT    0.031200    0.077500
BASF   0.02411
FVAR       0.16930
RESI 0
TWIN
CONF
TEMP  -100
CO1   4    0.264495    0.264495    0.000000    10.50000    0.00725    0.00725 =
         0.00959    0.00009   -0.00009   -0.00084
O1    6    0.399004    0.128971    0.087301    11.00000    0.01258    0.01377 =
         0.01559   -0.00149   -0.00749   -0.00122
O2    6    0.609748    0.098662    0.171082    11.00000    0.01613    0.01289 =
         0.01157    0.00097   -0.00455    0.00145
N1    5    0.451780    0.451780    0.000000    10.50000    0.01060    0.01060 =
         0.00836    0.00132   -0.00132   -0.00264
N2    5    0.076479    0.076479    0.000000    10.50000    0.01118    0.01118 =
         0.01168    0.00129   -0.00129   -0.00274
C1    1    0.432228    0.594441    0.040601    11.00000    0.01101    0.01343 =
         0.01121   -0.00047   -0.00083    0.00089
AFIX  43
H1    2    0.333376    0.608447    0.070386    11.00000   -1.20000
AFIX   0
C2    1    0.550154    0.720804    0.040567    11.00000    0.01269    0.00881 =
         0.01401   -0.00315    0.00236   -0.00144
AFIX  43
H2    2    0.530374    0.821965    0.067932    11.00000   -1.20000
AFIX   0
C3    1    0.698005    0.698005    0.000000    10.50000    0.01304    0.01304 =
         0.01358    0.00576   -0.00576   -0.00255
C4    1    0.829724    0.829724    0.000000    10.50000    0.01192    0.01192 =
         0.00959   -0.00420    0.00420   -0.00060
C5    1    0.787609    0.997478   -0.011138    11.00000    0.00734    0.01381 =
         0.01507   -0.00133   -0.00137   -0.00107
AFIX  43
H5    2    0.674208    1.030043   -0.018536    11.00000   -1.20000
AFIX   0
C6    1    0.114807   -0.086204    0.011182    11.00000    0.00761    0.01163 =
         0.01703    0.00019   -0.00080    0.00350
AFIX  43
H6    2    0.228860   -0.115205    0.019533    11.00000   -1.20000
AFIX   0
C7    1    0.529184    0.177993    0.120566    11.00000    0.01551    0.00937 =
         0.00971   -0.00035    0.00384    0.00047
AFIX  43
H7    2    0.571128    0.285066    0.106374    11.00000   -1.20000
AFIX   0
HKLF 4

REM  1 in P4(3)2(1)2                  New: P43212
REM R1 =  0.0354 for     951 Fo > 4sig(Fo)  and  0.0501 for all    1117 data
REM     90 parameters refined using      0 restraints

END

WGHT      0.0259      0.0690

REM Highest difference peak  0.367,  deepest hole -0.373,  1-sigma level  0.095
Q1    1   0.7408  0.1951  0.1218  11.00000  0.05    0.37
Q2    1   0.5611  0.4565  0.1378  11.00000  0.05    0.30
Q3    1   0.7233  0.0973  0.1660  11.00000  0.05    0.29
Q4    1   0.6115  0.1321  0.1542  11.00000  0.05    0.28
Q5    1   0.1939 -0.0251  0.0871  11.00000  0.05    0.27
Q6    1   0.3724  0.3748  0.1356  11.00000  0.05    0.27
Q7    1   0.2790  0.7417  0.0953  11.00000  0.05    0.26
Q8    1   0.6788 -0.0276  0.1537  11.00000  0.05    0.26
Q9    1   0.6064  0.3919  0.0991  11.00000  0.05    0.25
Q10   1   0.6442  0.2699  0.0795  11.00000  0.05    0.24
Q11   1   0.2376 -0.1258  0.1108  11.00000  0.05    0.24
Q12   1   0.6973  0.3437  0.1118  11.00000  0.05    0.23
Q13   1   0.6820  0.2245  0.1685  11.00000  0.05    0.23
Q14   1   0.6464  0.5247  0.1006  11.00000  0.05    0.23
Q15   1   0.1006 -0.0849  0.1117  11.00000  0.05    0.22
Q16   1   0.6677  0.7365  0.1264  11.00000  0.05    0.22
Q17   1   0.5958  0.8577  0.0980  11.00000  0.05    0.22
Q18   1   0.5159  0.3446  0.1474  11.00000  0.05    0.21
Q19   1   0.2654  0.6899  0.1487  11.00000  0.05    0.21
Q20   1   0.5644  0.9423  0.1290  11.00000  0.05    0.21
;
# start Validation Reply Form
_vrf_PLAT110_1                   
;
PROBLEM:    ADDSYM Detects Potential Lattice Translation ...          ? Check   
RESPONSE: other suitable space groups were not found by platon.                                            
;
_vrf_PLAT112_1                   
;
PROBLEM:   ADDSYM Detects New (Pseudo) Symm. Elem.        I        100 %Fit     
RESPONSE: other suitable space groups were not found by platon.                                             
;
# end Validation Reply Form

#===END
_shelx_res_checksum              71258
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1542274'
_audit_update_record             
;
2017-04-05 deposited with the CCDC.
2018-02-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H8 Cl Cu N2 O0'
_chemical_formula_weight         255.18

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'

_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_H-M   I41/acd

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y+1/4, x+3/4, z+1/4'
'-x+1/2, -y, z+1/2'
'y+1/4, -x+1/4, z+3/4'
'x, -y, -z+1/2'
'y+1/4, x+3/4, -z+3/4'
'-x+1/2, y, -z'
'-y+1/4, -x+1/4, -z+1/4'
'x+1/2, y+1/2, z+1/2'
'-y+3/4, x+5/4, z+3/4'
'-x+1, -y+1/2, z+1'
'y+3/4, -x+3/4, z+5/4'
'x+1/2, -y+1/2, -z+1'
'y+3/4, x+5/4, -z+5/4'
'-x+1, y+1/2, -z+1/2'
'-y+3/4, -x+3/4, -z+3/4'
'-x, -y, -z'
'y-1/4, -x-3/4, -z-1/4'
'x-1/2, y, -z-1/2'
'-y-1/4, x-1/4, -z-3/4'
'-x, y, z-1/2'
'-y-1/4, -x-3/4, z-3/4'
'x-1/2, -y, z'
'y-1/4, x-1/4, z-1/4'
'-x+1/2, -y+1/2, -z+1/2'
'y+1/4, -x-1/4, -z+1/4'
'x, y+1/2, -z'
'-y+1/4, x+1/4, -z-1/4'
'-x+1/2, y+1/2, z'
'-y+1/4, -x-1/4, z-1/4'
'x, -y+1/2, z+1/2'
'y+1/4, x+1/4, z+1/4'

_cell_length_a                   14.2202(5)
_cell_length_b                   14.2202(5)
_cell_length_c                   38.543(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     7793.9(9)
_cell_formula_units_Z            32
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1924
_cell_measurement_theta_min      2.87
_cell_measurement_theta_max      24.97

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.740
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             4095
_exptl_absorpt_coefficient_mu    2.471
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5037
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'


_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'TRIUMPH curved crystal monochromator'
_diffrn_measurement_device_type  'PHOTON100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10278
_diffrn_reflns_av_R_equivalents  0.0996
_diffrn_reflns_av_sigmaI/netI    0.0588
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_theta_min         2.86
_diffrn_reflns_theta_max         24.99
_reflns_number_total             1696
_reflns_number_gt                871
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0900P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1696
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1570
_refine_ls_R_factor_gt           0.0707
_refine_ls_wR_factor_ref         0.2041
_refine_ls_wR_factor_gt          0.1684
_refine_ls_goodness_of_fit_ref   1.196
_refine_ls_restrained_S_all      1.196
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu -0.93286(8) -0.31986(7) 0.01749(3) 0.0630(5) Uani 1 1 d . . .
Cl1 Cl -0.89792(13) -0.15597(13) 0.03185(6) 0.0539(6) Uani 1 1 d . . .
N1 N -0.9116(4) -0.3369(4) -0.03253(18) 0.0447(15) Uani 1 1 d . . .
N2 N -0.8741(4) -0.3931(4) 0.05544(19) 0.0532(17) Uani 1 1 d . . .
C1 C -0.8643(6) -0.2737(6) -0.0513(2) 0.063(2) Uani 1 1 d . . .
H1 H -0.8324 -0.2265 -0.0395 0.076 Uiso 1 1 calc R . .
C2 C -0.8594(6) -0.2736(6) -0.0869(3) 0.063(2) Uani 1 1 d . . .
H2 H -0.8249 -0.2276 -0.0984 0.076 Uiso 1 1 calc R . .
C3 C -0.9068(5) -0.3436(5) -0.1058(2) 0.0420(17) Uani 1 1 d . . .
C4 C -0.9525(5) -0.4112(5) -0.0863(3) 0.057(2) Uani 1 1 d . . .
H4 H -0.9825 -0.4613 -0.0971 0.068 Uiso 1 1 calc R . .
C5 C -0.9530(6) -0.4036(6) -0.0509(3) 0.061(2) Uani 1 1 d . . .
H5 H -0.9855 -0.4496 -0.0386 0.073 Uiso 1 1 calc R . .
C6 C -0.8197(5) -0.4682(6) 0.0494(2) 0.057(2) Uani 1 1 d . . .
H6 H -0.8099 -0.4872 0.0266 0.068 Uiso 1 1 calc R . .
C7 C -0.7771(5) -0.5188(5) 0.0762(2) 0.0491(19) Uani 1 1 d . . .
H7 H -0.7405 -0.5712 0.0709 0.059 Uiso 1 1 calc R . .
C8 C -0.7889(5) -0.4917(5) 0.1107(2) 0.0424(18) Uani 1 1 d . . .
C9 C -0.8480(5) -0.4136(5) 0.11641(19) 0.0455(18) Uani 1 1 d . . .
H9 H -0.8607 -0.3930 0.1388 0.055 Uiso 1 1 calc R . .
C10 C -0.8865(5) -0.3685(5) 0.0883(2) 0.053(2) Uani 1 1 d . . .
H10 H -0.9244 -0.3164 0.0927 0.064 Uiso 1 1 calc R . .

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 0.0770(8) 0.0707(8) 0.0412(8) 0.0071(5) -0.0059(5) 0.0122(5)
Cl1 0.0507(11) 0.0533(11) 0.0576(15) -0.0158(10) -0.0088(11) -0.0032(8)
N1 0.056(4) 0.045(3) 0.033(4) 0.002(3) -0.002(3) 0.001(3)
N2 0.055(4) 0.058(4) 0.047(5) -0.002(4) -0.001(3) 0.012(3)
C1 0.077(6) 0.058(5) 0.054(7) -0.003(5) 0.001(5) -0.013(4)
C2 0.078(6) 0.058(5) 0.054(7) -0.007(5) 0.001(5) -0.022(4)
C3 0.041(4) 0.052(4) 0.034(4) -0.002(4) 0.005(4) 0.008(3)
C4 0.062(5) 0.050(5) 0.058(7) 0.002(5) 0.000(5) -0.015(4)
C5 0.063(6) 0.059(5) 0.062(7) 0.013(5) 0.014(5) -0.009(4)
C6 0.060(5) 0.070(5) 0.040(6) 0.000(4) -0.002(4) 0.009(4)
C7 0.047(4) 0.060(5) 0.040(5) -0.001(4) 0.007(4) 0.009(3)
C8 0.043(4) 0.044(4) 0.040(5) 0.006(3) -0.002(3) 0.001(3)
C9 0.051(4) 0.056(5) 0.029(5) 0.000(4) 0.001(4) 0.007(3)
C10 0.058(5) 0.048(5) 0.053(6) -0.003(4) -0.005(5) 0.014(3)

_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 1.966(7) . ?
Cu1 N2 1.981(7) . ?
Cu1 Cl1 2.446(2) . ?
Cu1 Cl1 2.493(2) 11_244 ?
Cu1 Cu1 2.756(2) 11_244 ?
Cl1 Cu1 2.493(2) 11_244 ?
N1 C5 1.323(11) . ?
N1 C1 1.336(10) . ?
N2 C10 1.328(10) . ?
N2 C6 1.338(10) . ?
C1 C2 1.372(12) . ?
C1 H1 0.9300 . ?
C2 C3 1.406(11) . ?
C2 H2 0.9300 . ?
C3 C4 1.382(11) . ?
C3 C3 1.480(16) 16_334 ?
C4 C5 1.370(12) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 C7 1.396(10) . ?
C6 H6 0.9300 . ?
C7 C8 1.396(10) . ?
C7 H7 0.9300 . ?
C8 C9 1.411(9) . ?
C8 C8 1.454(14) 14_444 ?
C9 C10 1.372(10) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?

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 N2 126.5(3) . . ?
N1 Cu1 Cl1 107.92(18) . . ?
N2 Cu1 Cl1 104.4(2) . . ?
N1 Cu1 Cl1 110.45(19) . 11_244 ?
N2 Cu1 Cl1 99.8(2) . 11_244 ?
Cl1 Cu1 Cl1 106.09(8) . 11_244 ?
N1 Cu1 Cu1 101.27(16) . 11_244 ?
N2 Cu1 Cu1 132.2(2) . 11_244 ?
Cl1 Cu1 Cu1 56.90(6) . 11_244 ?
Cl1 Cu1 Cu1 55.29(6) 11_244 11_244 ?
Cu1 Cl1 Cu1 67.81(6) . 11_244 ?
C5 N1 C1 114.6(8) . . ?
C5 N1 Cu1 123.0(6) . . ?
C1 N1 Cu1 121.8(6) . . ?
C10 N2 C6 116.9(7) . . ?
C10 N2 Cu1 120.7(5) . . ?
C6 N2 Cu1 122.4(6) . . ?
N1 C1 C2 124.6(8) . . ?
N1 C1 H1 117.7 . . ?
C2 C1 H1 117.7 . . ?
C1 C2 C3 119.5(8) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C4 C3 C2 115.9(8) . . ?
C4 C3 C3 123.2(9) . 16_334 ?
C2 C3 C3 120.9(9) . 16_334 ?
C5 C4 C3 119.3(8) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
N1 C5 C4 126.0(8) . . ?
N1 C5 H5 117.0 . . ?
C4 C5 H5 117.0 . . ?
N2 C6 C7 122.3(8) . . ?
N2 C6 H6 118.8 . . ?
C7 C6 H6 118.8 . . ?
C6 C7 C8 120.6(7) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C7 C8 C9 116.0(7) . . ?
C7 C8 C8 122.7(8) . 14_444 ?
C9 C8 C8 121.3(9) . 14_444 ?
C10 C9 C8 118.9(7) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
N2 C10 C9 125.2(7) . . ?
N2 C10 H10 117.4 . . ?
C9 C10 H10 117.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 Cu1 Cl1 Cu1 91.97(18) . . . 11_244 ?
N2 Cu1 Cl1 Cu1 -131.3(2) . . . 11_244 ?
Cl1 Cu1 Cl1 Cu1 -26.43(12) 11_244 . . 11_244 ?
N2 Cu1 N1 C5 79.9(7) . . . . ?
Cl1 Cu1 N1 C5 -155.8(6) . . . . ?
Cl1 Cu1 N1 C5 -40.2(6) 11_244 . . . ?
Cu1 Cu1 N1 C5 -97.1(6) 11_244 . . . ?
N2 Cu1 N1 C1 -109.6(6) . . . . ?
Cl1 Cu1 N1 C1 14.7(7) . . . . ?
Cl1 Cu1 N1 C1 130.3(6) 11_244 . . . ?
Cu1 Cu1 N1 C1 73.3(6) 11_244 . . . ?
N1 Cu1 N2 C10 172.8(6) . . . . ?
Cl1 Cu1 N2 C10 47.0(7) . . . . ?
Cl1 Cu1 N2 C10 -62.5(7) 11_244 . . . ?
Cu1 Cu1 N2 C10 -11.1(8) 11_244 . . . ?
N1 Cu1 N2 C6 -6.3(8) . . . . ?
Cl1 Cu1 N2 C6 -132.1(6) . . . . ?
Cl1 Cu1 N2 C6 118.4(6) 11_244 . . . ?
Cu1 Cu1 N2 C6 169.8(5) 11_244 . . . ?
C5 N1 C1 C2 1.8(13) . . . . ?
Cu1 N1 C1 C2 -169.4(7) . . . . ?
N1 C1 C2 C3 0.2(14) . . . . ?
C1 C2 C3 C4 -2.8(12) . . . . ?
C1 C2 C3 C3 177.3(6) . . . 16_334 ?
C2 C3 C4 C5 3.3(11) . . . . ?
C3 C3 C4 C5 -176.9(6) 16_334 . . . ?
C1 N1 C5 C4 -1.3(12) . . . . ?
Cu1 N1 C5 C4 169.8(6) . . . . ?
C3 C4 C5 N1 -1.3(13) . . . . ?
C10 N2 C6 C7 -0.2(12) . . . . ?
Cu1 N2 C6 C7 178.9(6) . . . . ?
N2 C6 C7 C8 -0.9(12) . . . . ?
C6 C7 C8 C9 2.1(10) . . . . ?
C6 C7 C8 C8 -176.4(5) . . . 14_444 ?
C7 C8 C9 C10 -2.2(10) . . . . ?
C8 C8 C9 C10 176.3(5) 14_444 . . . ?
C6 N2 C10 C9 0.1(13) . . . . ?
Cu1 N2 C10 C9 -179.1(6) . . . . ?
C8 C9 C10 N2 1.2(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.595
_refine_diff_density_min         -0.712
_refine_diff_density_rms         0.119
