# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 923488'
_audit_update_record             
;
2015-09-06 deposited with the CCDC.
2015-09-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H24 Cl4 Cu2 N4 O4'
_chemical_formula_weight         781.22

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           Triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.6582(3)
_cell_length_b                   8.8071(4)
_cell_length_c                   11.4566(8)
_cell_angle_alpha                97.269(5)
_cell_angle_beta                 101.942(5)
_cell_angle_gamma                108.179(4)
_cell_volume                     702.91(6)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3586
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.846
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             382
_exptl_absorpt_coefficient_mu    1.948
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_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  graphite
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Eos.'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7568
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_sigmaI/netI    0.0307
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.90
_diffrn_reflns_theta_max         28.67
_reflns_number_total             3194
_reflns_number_gt                2834
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,Version 1.171.35.11 
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

_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)+(0.0409P)²+0.7568P] 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         3194
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0350
_refine_ls_wR_factor_ref         0.0922
_refine_ls_wR_factor_gt          0.0872
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.57545(5) 0.63215(4) 0.40610(3) 0.03232(12) Uani 1 1 d . . .
Cl1 Cl 0.71875(10) 0.58861(9) 0.58682(6) 0.03893(17) Uani 1 1 d . . .
Cl2 Cl 0.71496(11) 0.49869(9) 0.28260(7) 0.04244(18) Uani 1 1 d . . .
O1 O 0.2501(3) 1.2154(2) 0.02152(17) 0.0398(5) Uani 1 1 d . . .
O2 O 0.1327(3) 1.0195(2) -0.15720(16) 0.0388(5) Uani 1 1 d . . .
N1 N 0.4302(3) 0.6877(3) 0.2650(2) 0.0359(5) Uani 1 1 d . . .
N2 N 0.6662(3) 0.8806(2) 0.45753(18) 0.0246(4) Uani 1 1 d . . .
C1 C 0.2884(6) 0.5619(4) 0.1675(3) 0.0627(11) Uani 1 1 d . . .
H1A H 0.1634 0.5473 0.1803 0.075 Uiso 1 1 calc R . .
H1B H 0.3106 0.4597 0.1698 0.075 Uiso 1 1 calc R . .
C2 C 0.2906(4) 0.6001(3) 0.0486(2) 0.0325(6) Uani 1 1 d . . .
H2A H 0.1804 0.5216 -0.0116 0.039 Uiso 1 1 calc R . .
H2B H 0.4036 0.5900 0.0278 0.039 Uiso 1 1 calc R . .
C3 C 0.2891(3) 0.7667(3) 0.0435(2) 0.0243(5) Uani 1 1 d . . .
C4 C 0.2057(4) 0.8011(3) -0.0664(2) 0.0291(5) Uani 1 1 d . . .
H4 H 0.1545 0.7221 -0.1381 0.035 Uiso 1 1 calc R . .
C5 C 0.2031(3) 0.9559(3) -0.0632(2) 0.0263(5) Uani 1 1 d . . .
C6 C 0.2749(3) 1.0737(3) 0.0443(2) 0.0260(5) Uani 1 1 d . . .
C7 C 0.3560(4) 1.0446(3) 0.1526(2) 0.0266(5) Uani 1 1 d . . .
H7 H 0.4007 1.1244 0.2237 0.032 Uiso 1 1 calc R . .
C8 C 0.3697(3) 0.8874(3) 0.1526(2) 0.0233(5) Uani 1 1 d . . .
C9 C 0.4657(3) 0.8398(3) 0.2588(2) 0.0244(5) Uani 1 1 d . . .
C10 C 0.6133(3) 0.9558(3) 0.3671(2) 0.0231(5) Uani 1 1 d . . .
C11 C 0.6991(4) 1.1218(3) 0.3774(2) 0.0300(5) Uani 1 1 d . . .
H11 H 0.6680 1.1709 0.3127 0.036 Uiso 1 1 calc R . .
C12 C 0.8317(4) 1.2149(3) 0.4845(3) 0.0344(6) Uani 1 1 d . . .
H12 H 0.8884 1.3271 0.4933 0.041 Uiso 1 1 calc R . .
C13 C 0.8780(4) 1.1389(3) 0.5774(2) 0.0353(6) Uani 1 1 d . . .
H13 H 0.9635 1.1994 0.6511 0.042 Uiso 1 1 calc R . .
C14 C 0.7959(4) 0.9710(3) 0.5601(2) 0.0316(6) Uani 1 1 d . . .
H14 H 0.8321 0.9193 0.6219 0.038 Uiso 1 1 calc R . .
C15 C 0.1560(4) 1.1833(3) -0.1049(2) 0.0324(6) Uani 1 1 d . . .
H15A H 0.2312 1.2594 -0.1452 0.039 Uiso 1 1 calc R . .
H15B H 0.0327 1.1960 -0.1151 0.039 Uiso 1 1 calc R . .


_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 1.971(2) . ?
Cu1 N2 2.043(2) . ?
Cu1 Cl1 2.2718(7) . ?
Cu1 Cl2 2.3480(8) . ?
Cu1 Cl1 2.4990(8) 2_666 ?
Cl1 Cu1 2.4990(8) 2_666 ?
O1 C6 1.368(3) . ?
O1 C15 1.427(3) . ?
O2 C5 1.365(3) . ?
O2 C15 1.431(3) . ?
N1 C9 1.296(3) . ?
N1 C1 1.445(4) . ?
N2 C14 1.337(3) . ?
N2 C10 1.357(3) . ?
C1 C2 1.446(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.480(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.403(3) . ?
C3 C8 1.417(3) . ?
C4 C5 1.366(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.391(3) . ?
C6 C7 1.361(3) . ?
C7 C8 1.421(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.466(3) . ?
C9 C10 1.497(3) . ?
C10 C11 1.381(3) . ?
C11 C12 1.385(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.370(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.384(4) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?

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 78.87(8) . . ?
N1 Cu1 Cl1 170.69(8) . . ?
N2 Cu1 Cl1 96.17(6) . . ?
N1 Cu1 Cl2 92.06(8) . . ?
N2 Cu1 Cl2 122.61(6) . . ?
Cl1 Cu1 Cl2 97.25(3) . . ?
N1 Cu1 Cl1 90.53(7) . 2_666 ?
N2 Cu1 Cl1 132.16(6) . 2_666 ?
Cl1 Cu1 Cl1 87.00(3) . 2_666 ?
Cl2 Cu1 Cl1 104.09(3) . 2_666 ?
Cu1 Cl1 Cu1 93.00(3) . 2_666 ?
C6 O1 C15 106.33(19) . . ?
C5 O2 C15 106.02(19) . . ?
C9 N1 C1 119.6(2) . . ?
C9 N1 Cu1 119.14(17) . . ?
C1 N1 Cu1 121.22(18) . . ?
C14 N2 C10 119.0(2) . . ?
C14 N2 Cu1 125.82(17) . . ?
C10 N2 Cu1 113.96(15) . . ?
N1 C1 C2 112.7(3) . . ?
N1 C1 H1A 109.1 . . ?
C2 C1 H1A 109.1 . . ?
N1 C1 H1B 109.1 . . ?
C2 C1 H1B 109.1 . . ?
H1A C1 H1B 107.8 . . ?
C1 C2 C3 112.5(2) . . ?
C1 C2 H2A 109.1 . . ?
C3 C2 H2A 109.1 . . ?
C1 C2 H2B 109.1 . . ?
C3 C2 H2B 109.1 . . ?
H2A C2 H2B 107.8 . . ?
C4 C3 C8 121.7(2) . . ?
C4 C3 C2 120.2(2) . . ?
C8 C3 C2 118.0(2) . . ?
C5 C4 C3 117.0(2) . . ?
C5 C4 H4 121.5 . . ?
C3 C4 H4 121.5 . . ?
O2 C5 C4 128.1(2) . . ?
O2 C5 C6 110.0(2) . . ?
C4 C5 C6 121.9(2) . . ?
C7 C6 O1 127.8(2) . . ?
C7 C6 C5 122.8(2) . . ?
O1 C6 C5 109.5(2) . . ?
C6 C7 C8 117.3(2) . . ?
C6 C7 H7 121.3 . . ?
C8 C7 H7 121.3 . . ?
C3 C8 C7 119.2(2) . . ?
C3 C8 C9 116.4(2) . . ?
C7 C8 C9 124.3(2) . . ?
N1 C9 C8 121.3(2) . . ?
N1 C9 C10 113.5(2) . . ?
C8 C9 C10 125.1(2) . . ?
N2 C10 C11 120.8(2) . . ?
N2 C10 C9 113.0(2) . . ?
C11 C10 C9 126.0(2) . . ?
C12 C11 C10 119.7(2) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C13 C12 C11 119.0(2) . . ?
C13 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
C12 C13 C14 119.1(2) . . ?
C12 C13 H13 120.5 . . ?
C14 C13 H13 120.5 . . ?
N2 C14 C13 122.2(2) . . ?
N2 C14 H14 118.9 . . ?
C13 C14 H14 118.9 . . ?
O1 C15 O2 108.2(2) . . ?
O1 C15 H15A 110.1 . . ?
O2 C15 H15A 110.1 . . ?
O1 C15 H15B 110.1 . . ?
O2 C15 H15B 110.1 . . ?
H15A C15 H15B 108.4 . . ?

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
N2 Cu1 Cl1 Cu1 132.10(6) . . . 2_666 ?
Cl2 Cu1 Cl1 Cu1 -103.83(3) . . . 2_666 ?
Cl1 Cu1 Cl1 Cu1 0.0 2_666 . . 2_666 ?
N2 Cu1 N1 C9 7.1(2) . . . . ?
Cl1 Cu1 N1 C9 140.1(2) 2_666 . . . ?
N2 Cu1 N1 C1 -174.2(3) . . . . ?
Cl1 Cu1 N1 C1 -115.7(4) . . . . ?
Cl2 Cu1 N1 C1 62.9(3) . . . . ?
Cl1 Cu1 N1 C1 -41.2(3) 2_666 . . . ?
N1 Cu1 N2 C14 -177.9(2) . . . . ?
Cl1 Cu1 N2 C14 10.0(2) . . . . ?
Cl2 Cu1 N2 C14 -92.7(2) . . . . ?
Cl1 Cu1 N2 C14 101.6(2) 2_666 . . . ?
N1 Cu1 N2 C10 -10.82(17) . . . . ?
Cl1 Cu1 N2 C10 177.16(15) . . . . ?
Cl2 Cu1 N2 C10 74.46(17) . . . . ?
Cl1 Cu1 N2 C10 -91.29(17) 2_666 . . . ?
C9 N1 C1 C2 38.1(5) . . . . ?
Cu1 N1 C1 C2 -140.6(2) . . . . ?
N1 C1 C2 C3 -49.4(4) . . . . ?
C1 C2 C3 C4 -150.5(3) . . . . ?
C1 C2 C3 C8 28.0(4) . . . . ?
C8 C3 C4 C5 -0.9(4) . . . . ?
C2 C3 C4 C5 177.6(2) . . . . ?
C15 O2 C5 C4 177.2(3) . . . . ?
C15 O2 C5 C6 -1.9(3) . . . . ?
C3 C4 C5 O2 179.3(2) . . . . ?
C3 C4 C5 C6 -1.7(4) . . . . ?
C15 O1 C6 C7 -179.1(3) . . . . ?
C15 O1 C6 C5 1.1(3) . . . . ?
O2 C5 C6 C7 -179.3(2) . . . . ?
C4 C5 C6 C7 1.5(4) . . . . ?
O2 C5 C6 O1 0.6(3) . . . . ?
C4 C5 C6 O1 -178.6(2) . . . . ?
O1 C6 C7 C8 -178.5(2) . . . . ?
C5 C6 C7 C8 1.4(4) . . . . ?
C4 C3 C8 C7 3.8(4) . . . . ?
C2 C3 C8 C7 -174.8(2) . . . . ?
C4 C3 C8 C9 -175.3(2) . . . . ?
C2 C3 C8 C9 6.1(3) . . . . ?
C6 C7 C8 C3 -3.9(4) . . . . ?
C6 C7 C8 C9 175.1(2) . . . . ?
C1 N1 C9 C8 -2.3(4) . . . . ?
Cu1 N1 C9 C8 176.42(18) . . . . ?
C1 N1 C9 C10 179.0(3) . . . . ?
Cu1 N1 C9 C10 -2.2(3) . . . . ?
C3 C8 C9 N1 -20.4(4) . . . . ?
C7 C8 C9 N1 160.5(3) . . . . ?
C3 C8 C9 C10 158.1(2) . . . . ?
C7 C8 C9 C10 -21.0(4) . . . . ?
C14 N2 C10 C11 3.6(4) . . . . ?
Cu1 N2 C10 C11 -164.46(19) . . . . ?
C14 N2 C10 C9 -179.3(2) . . . . ?
Cu1 N2 C10 C9 12.7(2) . . . . ?
N1 C9 C10 N2 -7.1(3) . . . . ?
C8 C9 C10 N2 174.3(2) . . . . ?
N1 C9 C10 C11 169.8(3) . . . . ?
C8 C9 C10 C11 -8.8(4) . . . . ?
N2 C10 C11 C12 -4.4(4) . . . . ?
C9 C10 C11 C12 178.9(2) . . . . ?
C10 C11 C12 C13 1.4(4) . . . . ?
C11 C12 C13 C14 2.1(4) . . . . ?
C10 N2 C14 C13 0.1(4) . . . . ?
Cu1 N2 C14 C13 166.6(2) . . . . ?
C12 C13 C14 N2 -3.0(4) . . . . ?
C6 O1 C15 O2 -2.2(3) . . . . ?
C5 O2 C15 O1 2.6(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.881
_diffrn_reflns_theta_full        28.67
_diffrn_measured_fraction_theta_full 0.881
_refine_diff_density_max         0.755
_refine_diff_density_min         -0.597
_refine_diff_density_rms         0.069
####################################################################### 
# 
# 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_czf-hkb-m11-0902
_database_code_depnum_ccdc_archive 'CCDC 923489'
_audit_update_record             
;
2015-09-06 deposited with the CCDC.
2015-09-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H14 Cu N2 O7 S'
_chemical_formula_weight         429.90

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'
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbca

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

_cell_length_a                   7.36740(10)
_cell_length_b                   18.0273(3)
_cell_length_c                   23.5080(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3122.20(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6145
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.769
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1640
_exptl_absorpt_coefficient_mu    1.576
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_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  graphite
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Eos'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11090
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_sigmaI/netI    0.0209
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.11
_diffrn_reflns_theta_max         26.50
_reflns_number_total             3236
_reflns_number_gt                2934
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,Version 1.171.35.11
;
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

_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)+(0.0324P)²+2.8031P] 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         3236
_refine_ls_number_parameters     243
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0298
_refine_ls_R_factor_gt           0.0266
_refine_ls_wR_factor_ref         0.0728
_refine_ls_wR_factor_gt          0.0707
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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 0.38777(3) 0.337106(13) 0.038305(10) 0.01990(9) Uani 1 1 d . . .
S1 S 0.49766(7) 0.25696(3) -0.07989(2) 0.02058(12) Uani 1 1 d . . .
O1 O 0.4073(2) 0.31460(9) -0.04313(6) 0.0257(3) Uani 1 1 d . . .
O1W O 0.5373(2) 0.25249(9) 0.06125(7) 0.0271(3) Uani 1 1 d D . .
O2 O 0.4107(3) 0.64711(10) 0.26553(8) 0.0503(5) Uani 1 1 d . . .
O3 O 0.3525(3) 0.56804(10) 0.34077(7) 0.0508(5) Uani 1 1 d . . .
O4 O 0.3547(2) 0.21173(9) -0.10576(7) 0.0353(4) Uani 1 1 d . . .
O5 O 0.6088(2) 0.29295(10) -0.12193(7) 0.0394(4) Uani 1 1 d . . .
O6 O 0.6083(2) 0.20904(9) -0.04185(6) 0.0294(4) Uani 1 1 d . . .
N1 N 0.3738(2) 0.37368(9) 0.11692(7) 0.0221(4) Uani 1 1 d . . .
N2 N 0.3145(2) 0.44175(9) 0.02310(7) 0.0209(3) Uani 1 1 d . . .
C2 C 0.4027(3) 0.32546(12) 0.16642(9) 0.0273(5) Uani 1 1 d . . .
H2A H 0.5288 0.3282 0.1781 0.033 Uiso 1 1 calc R . .
H2B H 0.3765 0.2745 0.1560 0.033 Uiso 1 1 calc R . .
C3 C 0.2833(4) 0.34801(12) 0.21506(9) 0.0319(5) Uani 1 1 d . . .
H3A H 0.3125 0.3187 0.2484 0.038 Uiso 1 1 calc R . .
H3B H 0.1572 0.3392 0.2054 0.038 Uiso 1 1 calc R . .
C4 C 0.3119(3) 0.42906(12) 0.22769(9) 0.0259(4) Uani 1 1 d . . .
C5 C 0.3394(3) 0.47709(11) 0.18130(9) 0.0243(4) Uani 1 1 d . . .
C6 C 0.3371(3) 0.44346(11) 0.12441(8) 0.0214(4) Uani 1 1 d . . .
C7 C 0.2912(3) 0.48361(11) 0.07053(8) 0.0219(4) Uani 1 1 d . . .
C8 C 0.2752(3) 0.47035(12) -0.02778(9) 0.0278(5) Uani 1 1 d . . .
H8 H 0.2910 0.4411 -0.0600 0.033 Uiso 1 1 calc R . .
C9 C 0.2239(3) 0.55488(12) 0.06669(10) 0.0305(5) Uani 1 1 d . . .
H9 H 0.2046 0.5828 0.0994 0.037 Uiso 1 1 calc R . .
C10 C 0.3766(3) 0.55309(12) 0.19046(9) 0.0286(5) Uani 1 1 d . . .
H10 H 0.4005 0.5852 0.1604 0.034 Uiso 1 1 calc R . .
C11 C 0.3756(3) 0.57699(13) 0.24561(10) 0.0317(5) Uani 1 1 d . . .
C12 C 0.3431(3) 0.52966(13) 0.29081(9) 0.0335(5) Uani 1 1 d . . .
C13 C 0.3138(3) 0.45539(13) 0.28338(9) 0.0323(5) Uani 1 1 d . . .
H13 H 0.2960 0.4238 0.3142 0.039 Uiso 1 1 calc R . .
C14 C 0.3734(6) 0.64415(17) 0.32478(12) 0.0627(10) Uani 1 1 d . . .
H14A H 0.2631 0.6714 0.3332 0.075 Uiso 1 1 calc R . .
H14B H 0.4724 0.6664 0.3460 0.075 Uiso 1 1 calc R . .
C15 C 0.2117(3) 0.54203(13) -0.03425(10) 0.0326(5) Uani 1 1 d . . .
H15 H 0.1873 0.5611 -0.0702 0.039 Uiso 1 1 calc R . .
C16 C 0.1854(3) 0.58430(13) 0.01357(11) 0.0349(5) Uani 1 1 d . . .
H16 H 0.1419 0.6326 0.0104 0.042 Uiso 1 1 calc R . .
H2W H 0.568(4) 0.2334(17) 0.0312(8) 0.058(10) Uiso 1 1 d D . .
H1W H 0.634(2) 0.2653(16) 0.0760(12) 0.051(9) 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 O1W 1.9576(15) . ?
Cu1 O1 1.9620(14) . ?
Cu1 N1 1.9648(17) . ?
Cu1 N2 1.9944(17) . ?
Cu1 O6 2.2221(15) 3_455 ?
S1 O5 1.4383(16) . ?
S1 O4 1.4643(16) . ?
S1 O6 1.4867(15) . ?
S1 O1 1.5067(15) . ?
O1W H2W 0.817(10) . ?
O1W H1W 0.825(10) . ?
O2 C11 1.373(3) . ?
O2 C14 1.421(3) . ?
O3 C12 1.365(3) . ?
O3 C14 1.431(3) . ?
O6 Cu1 2.2221(15) 3 ?
N1 C6 1.299(3) . ?
N1 C2 1.468(3) . ?
N2 C8 1.334(3) . ?
N2 C7 1.357(3) . ?
C2 C3 1.498(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.506(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C13 1.393(3) . ?
C4 C5 1.407(3) . ?
C5 C10 1.413(3) . ?
C5 C6 1.468(3) . ?
C6 C7 1.498(3) . ?
C7 C9 1.380(3) . ?
C8 C15 1.383(3) . ?
C8 H8 0.9300 . ?
C9 C16 1.386(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.366(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.384(3) . ?
C12 C13 1.367(3) . ?
C13 H13 0.9300 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.372(3) . ?
C15 H15 0.9300 . ?
C16 H16 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
O1W Cu1 O1 93.81(6) . . ?
O1W Cu1 N1 91.83(7) . . ?
O1 Cu1 N1 172.25(7) . . ?
O1W Cu1 N2 159.85(7) . . ?
O1 Cu1 N2 92.32(7) . . ?
N1 Cu1 N2 80.62(7) . . ?
O1W Cu1 O6 102.68(6) . 3_455 ?
O1 Cu1 O6 91.55(6) . 3_455 ?
N1 Cu1 O6 92.39(6) . 3_455 ?
N2 Cu1 O6 96.32(7) . 3_455 ?
O5 S1 O4 112.05(11) . . ?
O5 S1 O6 111.29(10) . . ?
O4 S1 O6 108.70(10) . . ?
O5 S1 O1 109.56(10) . . ?
O4 S1 O1 107.72(9) . . ?
O6 S1 O1 107.35(8) . . ?
S1 O1 Cu1 137.27(9) . . ?
Cu1 O1W H2W 104(2) . . ?
Cu1 O1W H1W 112(2) . . ?
H2W O1W H1W 104(3) . . ?
C11 O2 C14 105.3(2) . . ?
C12 O3 C14 105.39(19) . . ?
S1 O6 Cu1 138.43(9) . 3 ?
C6 N1 C2 119.74(17) . . ?
C6 N1 Cu1 117.62(14) . . ?
C2 N1 Cu1 122.64(13) . . ?
C8 N2 C7 119.61(17) . . ?
C8 N2 Cu1 125.79(14) . . ?
C7 N2 Cu1 114.39(13) . . ?
N1 C2 C3 111.06(18) . . ?
N1 C2 H2A 109.4 . . ?
C3 C2 H2A 109.4 . . ?
N1 C2 H2B 109.4 . . ?
C3 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
C2 C3 C4 109.37(18) . . ?
C2 C3 H3A 109.8 . . ?
C4 C3 H3A 109.8 . . ?
C2 C3 H3B 109.8 . . ?
C4 C3 H3B 109.8 . . ?
H3A C3 H3B 108.2 . . ?
C13 C4 C5 121.14(19) . . ?
C13 C4 C3 121.16(19) . . ?
C5 C4 C3 117.68(18) . . ?
C4 C5 C10 120.42(19) . . ?
C4 C5 C6 116.74(18) . . ?
C10 C5 C6 122.76(19) . . ?
N1 C6 C5 121.40(18) . . ?
N1 C6 C7 113.60(17) . . ?
C5 C6 C7 124.99(17) . . ?
N2 C7 C9 120.62(19) . . ?
N2 C7 C6 113.43(17) . . ?
C9 C7 C6 125.89(19) . . ?
N2 C8 C15 122.2(2) . . ?
N2 C8 H8 118.9 . . ?
C15 C8 H8 118.9 . . ?
C7 C9 C16 119.2(2) . . ?
C7 C9 H9 120.4 . . ?
C16 C9 H9 120.4 . . ?
C11 C10 C5 116.7(2) . . ?
C11 C10 H10 121.7 . . ?
C5 C10 H10 121.7 . . ?
C10 C11 O2 127.8(2) . . ?
C10 C11 C12 122.4(2) . . ?
O2 C11 C12 109.8(2) . . ?
O3 C12 C13 127.9(2) . . ?
O3 C12 C11 109.9(2) . . ?
C13 C12 C11 122.2(2) . . ?
C12 C13 C4 117.1(2) . . ?
C12 C13 H13 121.5 . . ?
C4 C13 H13 121.5 . . ?
O2 C14 O3 108.3(2) . . ?
O2 C14 H14A 110.0 . . ?
O3 C14 H14A 110.0 . . ?
O2 C14 H14B 110.0 . . ?
O3 C14 H14B 110.0 . . ?
H14A C14 H14B 108.4 . . ?
C16 C15 C8 118.5(2) . . ?
C16 C15 H15 120.8 . . ?
C8 C15 H15 120.8 . . ?
C15 C16 C9 119.8(2) . . ?
C15 C16 H16 120.1 . . ?
C9 C16 H16 120.1 . . ?

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
O5 S1 O1 Cu1 -125.68(15) . . . . ?
O4 S1 O1 Cu1 112.19(15) . . . . ?
O6 S1 O1 Cu1 -4.71(17) . . . . ?
O1W Cu1 O1 S1 -0.22(15) . . . . ?
N2 Cu1 O1 S1 160.58(15) . . . . ?
O6 Cu1 O1 S1 -103.04(15) 3_455 . . . ?
O5 S1 O6 Cu1 -12.05(18) . . . 3 ?
O4 S1 O6 Cu1 111.82(15) . . . 3 ?
O1 S1 O6 Cu1 -131.92(14) . . . 3 ?
O1W Cu1 N1 C6 157.77(16) . . . . ?
N2 Cu1 N1 C6 -3.45(15) . . . . ?
O6 Cu1 N1 C6 -99.46(16) 3_455 . . . ?
O1W Cu1 N1 C2 -22.33(16) . . . . ?
N2 Cu1 N1 C2 176.46(17) . . . . ?
O6 Cu1 N1 C2 80.45(16) 3_455 . . . ?
O1W Cu1 N2 C8 115.7(2) . . . . ?
O1 Cu1 N2 C8 8.02(18) . . . . ?
N1 Cu1 N2 C8 -175.18(19) . . . . ?
O6 Cu1 N2 C8 -83.80(18) 3_455 . . . ?
O1W Cu1 N2 C7 -69.6(3) . . . . ?
O1 Cu1 N2 C7 -177.24(14) . . . . ?
N1 Cu1 N2 C7 -0.45(14) . . . . ?
O6 Cu1 N2 C7 90.94(14) 3_455 . . . ?
C6 N1 C2 C3 34.7(3) . . . . ?
Cu1 N1 C2 C3 -145.25(15) . . . . ?
N1 C2 C3 C4 -54.0(3) . . . . ?
C2 C3 C4 C13 -141.5(2) . . . . ?
C2 C3 C4 C5 37.4(3) . . . . ?
C13 C4 C5 C10 2.3(3) . . . . ?
C3 C4 C5 C10 -176.6(2) . . . . ?
C13 C4 C5 C6 179.2(2) . . . . ?
C3 C4 C5 C6 0.2(3) . . . . ?
C2 N1 C6 C5 5.5(3) . . . . ?
Cu1 N1 C6 C5 -174.63(15) . . . . ?
C2 N1 C6 C7 -173.67(17) . . . . ?
Cu1 N1 C6 C7 6.2(2) . . . . ?
C4 C5 C6 N1 -24.2(3) . . . . ?
C10 C5 C6 N1 152.6(2) . . . . ?
C4 C5 C6 C7 154.8(2) . . . . ?
C10 C5 C6 C7 -28.4(3) . . . . ?
C8 N2 C7 C9 1.3(3) . . . . ?
Cu1 N2 C7 C9 -173.79(16) . . . . ?
C8 N2 C7 C6 178.74(18) . . . . ?
Cu1 N2 C7 C6 3.7(2) . . . . ?
N1 C6 C7 N2 -6.4(3) . . . . ?
C5 C6 C7 N2 174.49(19) . . . . ?
N1 C6 C7 C9 170.9(2) . . . . ?
C5 C6 C7 C9 -8.2(3) . . . . ?
C7 N2 C8 C15 0.3(3) . . . . ?
Cu1 N2 C8 C15 174.83(17) . . . . ?
N2 C7 C9 C16 -2.0(3) . . . . ?
C6 C7 C9 C16 -179.1(2) . . . . ?
C4 C5 C10 C11 -2.9(3) . . . . ?
C6 C5 C10 C11 -179.6(2) . . . . ?
C5 C10 C11 O2 178.6(2) . . . . ?
C5 C10 C11 C12 1.1(4) . . . . ?
C14 O2 C11 C10 174.1(3) . . . . ?
C14 O2 C11 C12 -8.1(3) . . . . ?
C14 O3 C12 C13 -176.4(3) . . . . ?
C14 O3 C12 C11 6.1(3) . . . . ?
C10 C11 C12 O3 179.2(2) . . . . ?
O2 C11 C12 O3 1.3(3) . . . . ?
C10 C11 C12 C13 1.5(4) . . . . ?
O2 C11 C12 C13 -176.5(2) . . . . ?
O3 C12 C13 C4 -179.4(2) . . . . ?
C11 C12 C13 C4 -2.1(4) . . . . ?
C5 C4 C13 C12 0.2(4) . . . . ?
C3 C4 C13 C12 179.1(2) . . . . ?
C11 O2 C14 O3 11.7(4) . . . . ?
C12 O3 C14 O2 -11.0(4) . . . . ?
N2 C8 C15 C16 -1.2(4) . . . . ?
C8 C15 C16 C9 0.5(4) . . . . ?
C7 C9 C16 C15 1.1(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.50
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.058
####################################################################### 
# 
# 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_czf-hkb-mjm-cuclo4-2
_database_code_depnum_ccdc_archive 'CCDC 923490'
_audit_update_record             
;
2015-09-06 deposited with the CCDC.
2015-09-08 downloaded from the CCDC.
;
_audit_creation_date             2013-01-20
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C16 H12 Cl Cu N2 O8'
_chemical_formula_sum            'C16 H12 Cl Cu N2 O8'
_chemical_formula_weight         459.27
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   7.8720(4)
_cell_length_b                   17.1458(5)
_cell_length_c                   12.8986(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.085(5)
_cell_angle_gamma                90.00
_cell_volume                     1702.35(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4955
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.5350
_cell_measurement_theta_min      2.8671
_exptl_absorpt_coefficient_mu    1.492
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.792
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.11
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            17371
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.87
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 15.9784
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -15.00   24.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.2889  -99.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega -100.00  -61.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.2889 -178.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega  -21.00   54.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       21.3827  -77.0000  -30.0000 50

#__ type_ start__ end____ width___ exp.time_
  4 omega    4.00   55.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       21.3827   57.0000  -60.0000 34

#__ type_ start__ end____ width___ exp.time_
  5 omega   65.00  104.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       21.3827 -178.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
  6 omega  -20.00   73.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       21.3827   11.0000 -145.0000 62

#__ type_ start__ end____ width___ exp.time_
  7 omega   -8.00   85.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       21.3827    0.0000  -60.0000 62

#__ type_ start__ end____ width___ exp.time_
  8 omega  -44.00   11.50   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.2889   57.0000  150.0000 37

#__ type_ start__ end____ width___ exp.time_
  9 omega  -10.00   95.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       21.3827   38.0000   60.0000 70
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0104944000
_diffrn_orient_matrix_UB_12      0.0036682000
_diffrn_orient_matrix_UB_13      -0.0557634000
_diffrn_orient_matrix_UB_21      -0.0908659000
_diffrn_orient_matrix_UB_22      0.0046738000
_diffrn_orient_matrix_UB_23      -0.0048263000
_diffrn_orient_matrix_UB_31      0.0112817000
_diffrn_orient_matrix_UB_32      0.0409263000
_diffrn_orient_matrix_UB_33      0.0055718000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2681
_reflns_number_total             3478
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3478
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0403
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0347P)²+1.0488P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0849
_refine_ls_wR_factor_ref         0.0950
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.03590(5) 0.606755(19) 0.64395(3) 0.03412(13) Uani 1 1 d . . .
Cl1 Cl 0.33300(13) 0.52359(5) 0.82541(7) 0.0505(2) Uani 1 1 d . . .
O1 O -0.3770(4) 0.90926(14) 0.9492(2) 0.0618(7) Uani 1 1 d . . .
O2 O -0.4318(4) 0.82336(15) 1.0771(2) 0.0637(8) Uani 1 1 d . . .
O3 O 0.1056(3) 0.58943(10) 0.50734(15) 0.0328(5) Uani 1 1 d . . .
O4 O -0.0831(3) 0.50416(11) 0.61454(16) 0.0367(5) Uani 1 1 d . . .
O5 O 0.2997(4) 0.55908(16) 0.7217(2) 0.0635(8) Uani 1 1 d . . .
O6 O 0.3316(6) 0.5803(2) 0.9016(3) 0.1277(17) Uani 1 1 d . . .
O7 O 0.1958(5) 0.4700(2) 0.8284(3) 0.1062(13) Uani 1 1 d . . .
O8 O 0.4923(4) 0.4842(2) 0.8422(3) 0.0935(11) Uani 1 1 d . . .
N1 N 0.1021(4) 0.71769(13) 0.65447(19) 0.0339(6) Uani 1 1 d . . .
N2 N -0.0685(4) 0.63374(14) 0.7635(2) 0.0386(6) Uani 1 1 d . . .
C1 C 0.2076(5) 0.75403(17) 0.6022(3) 0.0420(8) Uani 1 1 d . . .
H1 H 0.2361 0.7295 0.5438 0.050 Uiso 1 1 calc R . .
C2 C 0.2763(5) 0.82661(18) 0.6312(3) 0.0477(9) Uani 1 1 d . . .
H2 H 0.3466 0.8515 0.5918 0.057 Uiso 1 1 calc R . .
C3 C 0.2385(5) 0.86143(18) 0.7196(3) 0.0461(9) Uani 1 1 d . . .
H3 H 0.2888 0.9090 0.7435 0.055 Uiso 1 1 calc R . .
C4 C 0.1248(5) 0.82513(17) 0.7729(3) 0.0436(8) Uani 1 1 d . . .
H4 H 0.0955 0.8488 0.8316 0.052 Uiso 1 1 calc R . .
C5 C 0.0556(4) 0.75401(16) 0.7385(2) 0.0335(7) Uani 1 1 d . . .
C6 C -0.0613(4) 0.70587(16) 0.7896(2) 0.0347(7) Uani 1 1 d . . .
C7 C -0.1585(4) 0.73715(17) 0.8656(2) 0.0368(7) Uani 1 1 d . . .
C8 C -0.2176(5) 0.81553(18) 0.8614(3) 0.0418(8) Uani 1 1 d . . .
H8 H -0.1963 0.8504 0.8104 0.050 Uiso 1 1 calc R . .
C9 C -0.3070(5) 0.83657(18) 0.9361(3) 0.0431(8) Uani 1 1 d . . .
C10 C -0.4605(6) 0.9008(2) 1.0364(3) 0.0620(11) Uani 1 1 d . . .
H10A H -0.5841 0.9103 1.0134 0.074 Uiso 1 1 calc R . .
H10B H -0.4137 0.9383 1.0913 0.074 Uiso 1 1 calc R . .
C11 C -0.3414(5) 0.7858(2) 1.0118(3) 0.0466(9) Uani 1 1 d . . .
C12 C -0.2910(5) 0.7094(2) 1.0159(3) 0.0467(9) Uani 1 1 d . . .
H12 H -0.3164 0.6755 1.0668 0.056 Uiso 1 1 calc R . .
C13 C -0.1995(5) 0.68470(18) 0.9402(2) 0.0402(8) Uani 1 1 d . . .
C14 C -0.1457(5) 0.60113(18) 0.9326(3) 0.0493(9) Uani 1 1 d . . .
H14A H -0.2170 0.5674 0.9663 0.059 Uiso 1 1 calc R . .
H14B H -0.0254 0.5945 0.9684 0.059 Uiso 1 1 calc R . .
C15 C -0.1677(5) 0.57994(18) 0.8170(3) 0.0492(9) Uani 1 1 d . . .
H15A H -0.1276 0.5270 0.8108 0.059 Uiso 1 1 calc R . .
H15B H -0.2898 0.5823 0.7830 0.059 Uiso 1 1 calc R . .
C16 C 0.0548(4) 0.52440(15) 0.4693(2) 0.0294(6) Uani 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 O3 1.9744(19) . ?
Cu1 O4 1.9917(19) . ?
Cu1 O5 2.262(3) . ?
Cu1 N1 1.969(2) . ?
Cu1 N2 1.948(3) . ?
Cl1 O5 1.442(2) . ?
Cl1 O6 1.383(3) . ?
Cl1 O7 1.425(3) . ?
Cl1 O8 1.401(3) . ?
O1 C9 1.387(4) . ?
O1 C10 1.424(4) . ?
O2 C10 1.428(4) . ?
O2 C11 1.372(4) . ?
O3 C16 1.250(3) . ?
O4 C16 1.248(3) 3_566 ?
N1 C1 1.330(4) . ?
N1 C5 1.364(4) . ?
N2 C6 1.280(4) . ?
N2 C15 1.471(4) . ?
C1 H1 0.9300 . ?
C1 C2 1.377(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.374(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.385(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.371(4) . ?
C5 C6 1.489(4) . ?
C6 C7 1.466(4) . ?
C7 C8 1.420(4) . ?
C7 C13 1.403(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.356(4) . ?
C9 C11 1.376(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.366(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.395(4) . ?
C13 C14 1.503(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.509(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 O4 1.248(3) 3_566 ?
C16 C16 1.536(6) 3_566 ?

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
O3 Cu1 O4 84.52(8) . . ?
O3 Cu1 O5 86.60(9) . . ?
O4 Cu1 O5 96.70(10) . . ?
N1 Cu1 O3 95.04(9) . . ?
N1 Cu1 O4 166.73(11) . . ?
N1 Cu1 O5 96.51(11) . . ?
N2 Cu1 O3 169.66(10) . . ?
N2 Cu1 O4 95.80(9) . . ?
N2 Cu1 O5 103.60(11) . . ?
N2 Cu1 N1 82.27(10) . . ?
O6 Cl1 O5 109.6(2) . . ?
O6 Cl1 O7 108.4(3) . . ?
O6 Cl1 O8 111.6(3) . . ?
O7 Cl1 O5 107.80(19) . . ?
O8 Cl1 O5 109.27(19) . . ?
O8 Cl1 O7 110.1(2) . . ?
C9 O1 C10 105.4(3) . . ?
C11 O2 C10 105.8(3) . . ?
C16 O3 Cu1 111.04(18) . . ?
C16 O4 Cu1 110.44(18) 3_566 . ?
Cl1 O5 Cu1 122.38(16) . . ?
C1 N1 Cu1 127.0(2) . . ?
C1 N1 C5 119.3(3) . . ?
C5 N1 Cu1 112.61(19) . . ?
C6 N2 Cu1 115.8(2) . . ?
C6 N2 C15 118.7(3) . . ?
C15 N2 Cu1 125.16(19) . . ?
N1 C1 H1 118.8 . . ?
N1 C1 C2 122.5(3) . . ?
C2 C1 H1 118.8 . . ?
C1 C2 H2 120.8 . . ?
C3 C2 C1 118.5(3) . . ?
C3 C2 H2 120.8 . . ?
C2 C3 H3 120.3 . . ?
C2 C3 C4 119.4(3) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.6(3) . . ?
C5 C4 H4 120.2 . . ?
N1 C5 C4 120.6(3) . . ?
N1 C5 C6 113.1(2) . . ?
C4 C5 C6 126.2(3) . . ?
N2 C6 C5 114.6(3) . . ?
N2 C6 C7 122.0(3) . . ?
C7 C6 C5 123.4(2) . . ?
C8 C7 C6 122.2(3) . . ?
C13 C7 C6 116.8(3) . . ?
C13 C7 C8 120.8(3) . . ?
C7 C8 H8 122.0 . . ?
C9 C8 C7 116.1(3) . . ?
C9 C8 H8 122.0 . . ?
C8 C9 O1 127.1(3) . . ?
C8 C9 C11 123.0(3) . . ?
C11 C9 O1 109.9(3) . . ?
O1 C10 O2 108.8(3) . . ?
O1 C10 H10A 109.9 . . ?
O1 C10 H10B 109.9 . . ?
O2 C10 H10A 109.9 . . ?
O2 C10 H10B 109.9 . . ?
H10A C10 H10B 108.3 . . ?
O2 C11 C9 110.0(3) . . ?
C12 C11 O2 127.6(3) . . ?
C12 C11 C9 122.3(3) . . ?
C11 C12 H12 121.5 . . ?
C11 C12 C13 116.9(3) . . ?
C13 C12 H12 121.5 . . ?
C7 C13 C14 117.2(3) . . ?
C12 C13 C7 120.8(3) . . ?
C12 C13 C14 122.0(3) . . ?
C13 C14 H14A 110.0 . . ?
C13 C14 H14B 110.0 . . ?
C13 C14 C15 108.6(3) . . ?
H14A C14 H14B 108.4 . . ?
C15 C14 H14A 110.0 . . ?
C15 C14 H14B 110.0 . . ?
N2 C15 C14 110.5(3) . . ?
N2 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
O3 C16 C16 116.8(3) . 3_566 ?
O4 C16 O3 126.1(3) 3_566 . ?
O4 C16 C16 117.1(3) 3_566 3_566 ?

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 O3 C16 O4 -177.8(3) . . . 3_566 ?
Cu1 O3 C16 C16 3.1(4) . . . 3_566 ?
Cu1 N1 C1 C2 -165.3(3) . . . . ?
Cu1 N1 C5 C4 164.9(3) . . . . ?
Cu1 N1 C5 C6 -10.6(3) . . . . ?
Cu1 N2 C6 C5 -11.6(4) . . . . ?
Cu1 N2 C6 C7 169.7(2) . . . . ?
Cu1 N2 C15 C14 149.1(3) . . . . ?
O1 C9 C11 O2 -0.9(4) . . . . ?
O1 C9 C11 C12 178.4(3) . . . . ?
O2 C11 C12 C13 -180.0(3) . . . . ?
O3 Cu1 O4 C16 2.8(2) . . . 3_566 ?
O3 Cu1 O5 Cl1 -155.2(2) . . . . ?
O3 Cu1 N1 C1 -18.3(3) . . . . ?
O3 Cu1 N1 C5 173.9(2) . . . . ?
O3 Cu1 N2 C6 -70.9(6) . . . . ?
O3 Cu1 N2 C15 102.6(5) . . . . ?
O4 Cu1 O3 C16 -3.3(2) . . . . ?
O4 Cu1 O5 Cl1 -71.1(2) . . . . ?
O4 Cu1 N1 C1 -105.8(5) . . . . ?
O4 Cu1 N1 C5 86.4(4) . . . . ?
O4 Cu1 N2 C6 -162.2(2) . . . . ?
O4 Cu1 N2 C15 11.4(3) . . . . ?
O5 Cu1 O3 C16 93.8(2) . . . . ?
O5 Cu1 O4 C16 -83.1(2) . . . 3_566 ?
O5 Cu1 N1 C1 68.8(3) . . . . ?
O5 Cu1 N1 C5 -99.0(2) . . . . ?
O5 Cu1 N2 C6 99.5(3) . . . . ?
O5 Cu1 N2 C15 -87.0(3) . . . . ?
O6 Cl1 O5 Cu1 -70.8(3) . . . . ?
O7 Cl1 O5 Cu1 46.9(3) . . . . ?
O8 Cl1 O5 Cu1 166.6(2) . . . . ?
N1 Cu1 O3 C16 -170.0(2) . . . . ?
N1 Cu1 O4 C16 91.6(4) . . . 3_566 ?
N1 Cu1 O5 Cl1 110.1(2) . . . . ?
N1 Cu1 N2 C6 4.6(3) . . . . ?
N1 Cu1 N2 C15 178.1(3) . . . . ?
N1 C1 C2 C3 2.2(6) . . . . ?
N1 C5 C6 N2 14.8(4) . . . . ?
N1 C5 C6 C7 -166.5(3) . . . . ?
N2 Cu1 O3 C16 -95.6(5) . . . . ?
N2 Cu1 O4 C16 172.5(2) . . . 3_566 ?
N2 Cu1 O5 Cl1 26.5(2) . . . . ?
N2 Cu1 N1 C1 171.7(3) . . . . ?
N2 Cu1 N1 C5 3.9(2) . . . . ?
N2 C6 C7 C8 -150.8(3) . . . . ?
N2 C6 C7 C13 25.8(5) . . . . ?
C1 N1 C5 C4 -3.9(5) . . . . ?
C1 N1 C5 C6 -179.4(3) . . . . ?
C1 C2 C3 C4 -4.0(6) . . . . ?
C2 C3 C4 C5 1.9(6) . . . . ?
C3 C4 C5 N1 2.1(5) . . . . ?
C3 C4 C5 C6 177.0(3) . . . . ?
C4 C5 C6 N2 -160.5(3) . . . . ?
C4 C5 C6 C7 18.3(5) . . . . ?
C5 N1 C1 C2 1.8(5) . . . . ?
C5 C6 C7 C8 30.6(5) . . . . ?
C5 C6 C7 C13 -152.8(3) . . . . ?
C6 N2 C15 C14 -37.6(5) . . . . ?
C6 C7 C8 C9 179.5(3) . . . . ?
C6 C7 C13 C12 179.7(3) . . . . ?
C6 C7 C13 C14 -2.1(5) . . . . ?
C7 C8 C9 O1 179.6(3) . . . . ?
C7 C8 C9 C11 -0.6(5) . . . . ?
C7 C13 C14 C15 -36.9(5) . . . . ?
C8 C7 C13 C12 -3.7(5) . . . . ?
C8 C7 C13 C14 174.5(3) . . . . ?
C8 C9 C11 O2 179.3(3) . . . . ?
C8 C9 C11 C12 -1.4(6) . . . . ?
C9 O1 C10 O2 2.6(4) . . . . ?
C9 C11 C12 C13 0.9(5) . . . . ?
C10 O1 C9 C8 178.7(4) . . . . ?
C10 O1 C9 C11 -1.1(4) . . . . ?
C10 O2 C11 C9 2.4(4) . . . . ?
C10 O2 C11 C12 -176.8(4) . . . . ?
C11 O2 C10 O1 -3.1(4) . . . . ?
C11 C12 C13 C7 1.6(5) . . . . ?
C11 C12 C13 C14 -176.5(3) . . . . ?
C12 C13 C14 C15 141.2(4) . . . . ?
C13 C7 C8 C9 3.1(5) . . . . ?
C13 C14 C15 N2 56.2(4) . . . . ?
C15 N2 C6 C5 174.5(3) . . . . ?
C15 N2 C6 C7 -4.3(5) . . . . ?

