# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_anchcu1
_database_code_depnum_ccdc_archive 'CCDC 1052906'
_audit_update_record             
;
2015-03-09 deposited with the CCDC.
2015-04-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H19 Cl Cu N6 S, 0.15(C H4 O)'
_chemical_formula_sum            'C13.15 H19.60 Cl Cu N6 O0.15 S'
_chemical_formula_weight         395.20

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n
_symmetry_space_group_name_Hall  '-P 2yn'

loop_
_symmetry_equiv_pos_as_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                   7.6944(5)
_cell_length_b                   17.4966(10)
_cell_length_c                   13.1409(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.615(2)
_cell_angle_gamma                90.00
_cell_volume                     1726.40(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9871
_cell_measurement_theta_min      2.83
_cell_measurement_theta_max      29.88

_exptl_crystal_description       needle
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             815
_exptl_absorpt_coefficient_mu    1.547
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6929
_exptl_absorpt_correction_T_max  0.9712
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            35395
_diffrn_reflns_av_R_equivalents  0.0728
_diffrn_reflns_av_sigmaI/netI    0.0303
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.97
_diffrn_reflns_theta_max         25.35
_reflns_number_total             3148
_reflns_number_gt                2751
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0239P)²+2.7620P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3148
_refine_ls_number_parameters     210
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0334
_refine_ls_wR_factor_ref         0.0753
_refine_ls_wR_factor_gt          0.0723
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.003
_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 0.53921(4) 0.313159(17) 0.46668(2) 0.01613(10) Uani 1 1 d . . .
Cl1 Cl 0.44289(9) 0.32166(4) 0.63393(5) 0.02196(16) Uani 1 1 d . . .
S1 S 0.83514(9) 0.29061(4) 0.52484(5) 0.01990(16) Uani 1 1 d . . .
N1 N 0.3214(3) 0.35557(12) 0.37922(17) 0.0192(5) Uani 1 1 d . . .
N2 N 0.6223(3) 0.41844(12) 0.43829(17) 0.0190(5) Uani 1 1 d . . .
N3 N 0.7919(3) 0.44227(13) 0.47343(18) 0.0209(5) Uani 1 1 d . . .
N4 N 1.0694(3) 0.40378(13) 0.55320(18) 0.0228(5) Uani 1 1 d . . .
H4A H 1.1057 0.4511 0.5485 0.027 Uiso 1 1 calc R . .
H4B H 1.1455 0.3684 0.5823 0.027 Uiso 1 1 calc R . .
N5 N 0.3902(3) 0.20988(12) 0.41350(17) 0.0178(5) Uani 1 1 d . . .
N6 N 0.6337(3) 0.08623(13) 0.3957(2) 0.0276(6) Uani 1 1 d . . .
C1 C 0.1763(3) 0.31329(16) 0.3521(2) 0.0196(6) Uani 1 1 d . . .
C2 C 0.0192(4) 0.34417(17) 0.2929(2) 0.0237(6) Uani 1 1 d . . .
H2 H -0.0848 0.3138 0.2720 0.028 Uiso 1 1 calc R . .
C3 C 0.0199(4) 0.42071(17) 0.2654(2) 0.0266(7) Uani 1 1 d . . .
H3 H -0.0857 0.4434 0.2260 0.032 Uiso 1 1 calc R . .
C4 C 0.1729(4) 0.46454(16) 0.2948(2) 0.0248(6) Uani 1 1 d . . .
H4 H 0.1732 0.5170 0.2761 0.030 Uiso 1 1 calc R . .
C5 C 0.3254(4) 0.42990(16) 0.3520(2) 0.0214(6) Uani 1 1 d . . .
C6 C 0.5008(4) 0.46401(15) 0.3874(2) 0.0223(6) Uani 1 1 d . . .
H6 H 0.5245 0.5159 0.3742 0.027 Uiso 1 1 calc R . .
C7 C 0.8999(3) 0.38581(15) 0.5165(2) 0.0176(6) Uani 1 1 d . . .
C8 C 0.1997(3) 0.23397(15) 0.3966(2) 0.0216(6) Uani 1 1 d . . .
H8A H 0.1613 0.2327 0.4638 0.026 Uiso 1 1 calc R . .
H8B H 0.1241 0.1979 0.3482 0.026 Uiso 1 1 calc R . .
C9 C 0.4278(4) 0.18582(16) 0.3121(2) 0.0241(6) Uani 1 1 d . . .
H9A H 0.4164 0.2305 0.2648 0.029 Uiso 1 1 calc R . .
H9B H 0.3389 0.1472 0.2794 0.029 Uiso 1 1 calc R . .
C10 C 0.6123(4) 0.15255(17) 0.3258(2) 0.0274(7) Uani 1 1 d . . .
H10A H 0.6331 0.1369 0.2570 0.033 Uiso 1 1 calc R . .
H10B H 0.7017 0.1919 0.3550 0.033 Uiso 1 1 calc R . .
C11 C 0.6000(4) 0.10850(16) 0.4967(2) 0.0256(6) Uani 1 1 d . . .
H11A H 0.6904 0.1463 0.5300 0.031 Uiso 1 1 calc R . .
H11B H 0.6108 0.0631 0.5427 0.031 Uiso 1 1 calc R . .
C12 C 0.4156(4) 0.14283(15) 0.4848(2) 0.0230(6) Uani 1 1 d . . .
H12A H 0.3250 0.1035 0.4570 0.028 Uiso 1 1 calc R . .
H12B H 0.3978 0.1588 0.5540 0.028 Uiso 1 1 calc R . .
C13 C 0.8131(4) 0.05462(19) 0.4087(3) 0.0379(8) Uani 1 1 d . . .
H13A H 0.8217 0.0073 0.4494 0.057 Uiso 1 1 calc R . .
H13B H 0.9001 0.0917 0.4455 0.057 Uiso 1 1 calc R . .
H13C H 0.8378 0.0437 0.3401 0.057 Uiso 1 1 calc R . .
O1 O 0.632(2) 0.3494(9) 0.1165(11) 0.037(4) Uiso 0.15 1 d PD . .
H1 H 0.6754 0.3054 0.1272 0.056 Uiso 0.15 1 calc PRD . .
C14 C 0.554(3) 0.3695(12) 0.1963(15) 0.030(5) Uiso 0.15 1 d PD . .
H14A H 0.4245 0.3627 0.1744 0.045 Uiso 0.15 1 calc PR . .
H14B H 0.5807 0.4231 0.2148 0.045 Uiso 0.15 1 calc PR . .
H14C H 0.6000 0.3370 0.2569 0.045 Uiso 0.15 1 calc PR . .


_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 1.959(2) . ?
Cu1 N2 2.011(2) . ?
Cu1 N5 2.172(2) . ?
Cu1 S1 2.2725(7) . ?
Cu1 Cl1 2.4724(7) . ?
S1 C7 1.749(3) . ?
N1 C1 1.321(3) . ?
N1 C5 1.351(4) . ?
N2 C6 1.298(3) . ?
N2 N3 1.352(3) . ?
N3 C7 1.334(3) . ?
N4 C7 1.326(3) . ?
N4 H4A 0.8800 . ?
N4 H4B 0.8800 . ?
N5 C9 1.485(3) . ?
N5 C12 1.487(3) . ?
N5 C8 1.494(3) . ?
N6 C11 1.461(4) . ?
N6 C13 1.462(4) . ?
N6 C10 1.467(4) . ?
C1 C2 1.396(4) . ?
C1 C8 1.501(4) . ?
C2 C3 1.387(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.387(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.388(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.456(4) . ?
C6 H6 0.9500 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.509(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.517(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
O1 C14 1.363(19) . ?
O1 H1 0.8400 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

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 79.07(9) . . ?
N1 Cu1 N5 78.60(9) . . ?
N2 Cu1 N5 150.35(9) . . ?
N1 Cu1 S1 158.26(7) . . ?
N2 Cu1 S1 83.43(7) . . ?
N5 Cu1 S1 112.56(6) . . ?
N1 Cu1 Cl1 96.58(7) . . ?
N2 Cu1 Cl1 106.20(7) . . ?
N5 Cu1 Cl1 95.53(6) . . ?
S1 Cu1 Cl1 100.62(3) . . ?
C7 S1 Cu1 95.27(9) . . ?
C1 N1 C5 122.3(2) . . ?
C1 N1 Cu1 120.66(18) . . ?
C5 N1 Cu1 116.97(18) . . ?
C6 N2 N3 121.3(2) . . ?
C6 N2 Cu1 115.82(18) . . ?
N3 N2 Cu1 122.78(17) . . ?
C7 N3 N2 112.4(2) . . ?
C7 N4 H4A 120.0 . . ?
C7 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
C9 N5 C12 108.5(2) . . ?
C9 N5 C8 108.9(2) . . ?
C12 N5 C8 107.8(2) . . ?
C9 N5 Cu1 109.38(16) . . ?
C12 N5 Cu1 117.78(16) . . ?
C8 N5 Cu1 104.17(15) . . ?
C11 N6 C13 110.2(2) . . ?
C11 N6 C10 109.9(2) . . ?
C13 N6 C10 110.3(2) . . ?
N1 C1 C2 120.7(3) . . ?
N1 C1 C8 113.0(2) . . ?
C2 C1 C8 126.2(3) . . ?
C3 C2 C1 117.8(3) . . ?
C3 C2 H2 121.1 . . ?
C1 C2 H2 121.1 . . ?
C4 C3 C2 120.8(3) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 118.4(3) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 H4 120.8 . . ?
N1 C5 C4 119.9(3) . . ?
N1 C5 C6 112.6(2) . . ?
C4 C5 C6 127.5(3) . . ?
N2 C6 C5 115.2(2) . . ?
N2 C6 H6 122.4 . . ?
C5 C6 H6 122.4 . . ?
N4 C7 N3 116.8(2) . . ?
N4 C7 S1 118.3(2) . . ?
N3 C7 S1 124.9(2) . . ?
N5 C8 C1 110.4(2) . . ?
N5 C8 H8A 109.6 . . ?
C1 C8 H8A 109.6 . . ?
N5 C8 H8B 109.6 . . ?
C1 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
N5 C9 C10 111.4(2) . . ?
N5 C9 H9A 109.3 . . ?
C10 C9 H9A 109.3 . . ?
N5 C9 H9B 109.3 . . ?
C10 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
N6 C10 C9 110.7(2) . . ?
N6 C10 H10A 109.5 . . ?
C9 C10 H10A 109.5 . . ?
N6 C10 H10B 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
N6 C11 C12 111.1(2) . . ?
N6 C11 H11A 109.4 . . ?
C12 C11 H11A 109.4 . . ?
N6 C11 H11B 109.4 . . ?
C12 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
N5 C12 C11 111.6(2) . . ?
N5 C12 H12A 109.3 . . ?
C11 C12 H12A 109.3 . . ?
N5 C12 H12B 109.3 . . ?
C11 C12 H12B 109.3 . . ?
H12A C12 H12B 108.0 . . ?
N6 C13 H13A 109.5 . . ?
N6 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N6 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C14 O1 H1 109.5 . . ?
O1 C14 H14A 109.5 . . ?
O1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 Cu1 S1 C7 44.3(2) . . . . ?
N2 Cu1 S1 C7 7.88(11) . . . . ?
N5 Cu1 S1 C7 161.96(11) . . . . ?
Cl1 Cu1 S1 C7 -97.43(9) . . . . ?
N2 Cu1 N1 C1 177.2(2) . . . . ?
N5 Cu1 N1 C1 16.8(2) . . . . ?
S1 Cu1 N1 C1 140.28(18) . . . . ?
Cl1 Cu1 N1 C1 -77.5(2) . . . . ?
N2 Cu1 N1 C5 -5.28(19) . . . . ?
N5 Cu1 N1 C5 -165.6(2) . . . . ?
S1 Cu1 N1 C5 -42.2(3) . . . . ?
Cl1 Cu1 N1 C5 100.01(19) . . . . ?
N1 Cu1 N2 C6 5.3(2) . . . . ?
N5 Cu1 N2 C6 47.0(3) . . . . ?
S1 Cu1 N2 C6 172.3(2) . . . . ?
Cl1 Cu1 N2 C6 -88.5(2) . . . . ?
N1 Cu1 N2 N3 -177.6(2) . . . . ?
N5 Cu1 N2 N3 -135.8(2) . . . . ?
S1 Cu1 N2 N3 -10.53(19) . . . . ?
Cl1 Cu1 N2 N3 88.67(19) . . . . ?
C6 N2 N3 C7 -175.0(2) . . . . ?
Cu1 N2 N3 C7 8.0(3) . . . . ?
N1 Cu1 N5 C9 87.27(17) . . . . ?
N2 Cu1 N5 C9 45.4(3) . . . . ?
S1 Cu1 N5 C9 -73.18(17) . . . . ?
Cl1 Cu1 N5 C9 -177.11(15) . . . . ?
N1 Cu1 N5 C12 -148.3(2) . . . . ?
N2 Cu1 N5 C12 169.85(18) . . . . ?
S1 Cu1 N5 C12 51.2(2) . . . . ?
Cl1 Cu1 N5 C12 -52.71(18) . . . . ?
N1 Cu1 N5 C8 -29.04(16) . . . . ?
N2 Cu1 N5 C8 -70.9(2) . . . . ?
S1 Cu1 N5 C8 170.51(14) . . . . ?
Cl1 Cu1 N5 C8 66.58(16) . . . . ?
C5 N1 C1 C2 0.4(4) . . . . ?
Cu1 N1 C1 C2 177.8(2) . . . . ?
C5 N1 C1 C8 -176.3(2) . . . . ?
Cu1 N1 C1 C8 1.0(3) . . . . ?
N1 C1 C2 C3 -1.3(4) . . . . ?
C8 C1 C2 C3 175.0(3) . . . . ?
C1 C2 C3 C4 1.0(4) . . . . ?
C2 C3 C4 C5 0.2(4) . . . . ?
C1 N1 C5 C4 0.8(4) . . . . ?
Cu1 N1 C5 C4 -176.6(2) . . . . ?
C1 N1 C5 C6 -178.0(2) . . . . ?
Cu1 N1 C5 C6 4.5(3) . . . . ?
C3 C4 C5 N1 -1.1(4) . . . . ?
C3 C4 C5 C6 177.6(3) . . . . ?
N3 N2 C6 C5 178.4(2) . . . . ?
Cu1 N2 C6 C5 -4.4(3) . . . . ?
N1 C5 C6 N2 0.0(4) . . . . ?
C4 C5 C6 N2 -178.7(3) . . . . ?
N2 N3 C7 N4 180.0(2) . . . . ?
N2 N3 C7 S1 1.5(3) . . . . ?
Cu1 S1 C7 N4 173.7(2) . . . . ?
Cu1 S1 C7 N3 -7.9(2) . . . . ?
C9 N5 C8 C1 -78.9(3) . . . . ?
C12 N5 C8 C1 163.6(2) . . . . ?
Cu1 N5 C8 C1 37.7(2) . . . . ?
N1 C1 C8 N5 -28.1(3) . . . . ?
C2 C1 C8 N5 155.4(3) . . . . ?
C12 N5 C9 C10 -56.6(3) . . . . ?
C8 N5 C9 C10 -173.7(2) . . . . ?
Cu1 N5 C9 C10 73.1(2) . . . . ?
C11 N6 C10 C9 -58.1(3) . . . . ?
C13 N6 C10 C9 -179.8(2) . . . . ?
N5 C9 C10 N6 58.9(3) . . . . ?
C13 N6 C11 C12 179.0(2) . . . . ?
C10 N6 C11 C12 57.2(3) . . . . ?
C9 N5 C12 C11 55.7(3) . . . . ?
C8 N5 C12 C11 173.4(2) . . . . ?
Cu1 N5 C12 C11 -69.2(3) . . . . ?
N6 C11 C12 N5 -57.2(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N4 H4B Cl1 0.88 2.38 3.181(2) 150.6 1_655
N4 H4A N3 0.88 2.07 2.946(3) 173.7 3_766

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.517
_refine_diff_density_min         -0.415
_refine_diff_density_rms         0.100
####################################################################### 
# 
# 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_feba235
_database_code_depnum_ccdc_archive 'CCDC 1052907'
_audit_update_record             
;
2015-03-09 deposited with the CCDC.
2015-04-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H21 Cl Cu N6 O3 S'
_chemical_formula_sum            'C17 H21 Cl Cu N6 O3 S'
_chemical_formula_weight         488.45

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'
S S 0.1246 0.1234 '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
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   8.0848(4)
_cell_length_b                   12.1277(6)
_cell_length_c                   12.3563(5)
_cell_angle_alpha                63.8664(17)
_cell_angle_beta                 83.4075(18)
_cell_angle_gamma                73.0771(17)
_cell_volume                     1040.45(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9856
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      30.06

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             502
_exptl_absorpt_coefficient_mu    1.310
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8802
_exptl_absorpt_correction_T_max  0.9255
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            32188
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_av_sigmaI/netI    0.0373
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.94
_diffrn_reflns_theta_max         30.14
_reflns_number_total             6092
_reflns_number_gt                4901
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0313P)²+0.6765P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6092
_refine_ls_number_parameters     265
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0326
_refine_ls_wR_factor_ref         0.0745
_refine_ls_wR_factor_gt          0.0695
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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 0.22097(2) 0.663584(19) 0.161027(19) 0.01147(6) Uani 1 1 d . . .
Cl1 Cl -0.00951(5) 0.64442(4) 0.08289(4) 0.01649(9) Uani 1 1 d . . .
S1 S 0.09305(5) 0.86834(4) 0.13340(4) 0.01511(9) Uani 1 1 d . . .
O1 O 0.32369(19) 0.06207(13) 0.64391(12) 0.0252(3) Uani 1 1 d . . .
O2 O 0.39956(17) 0.23667(13) 0.50677(13) 0.0231(3) Uani 1 1 d . . .
O3 O 0.20292(19) 0.57355(12) 0.35732(12) 0.0240(3) Uani 1 1 d . . .
N1 N 0.40213(17) 0.49464(13) 0.17494(13) 0.0114(3) Uani 1 1 d . . .
N2 N 0.42733(17) 0.72865(13) 0.09993(13) 0.0123(3) Uani 1 1 d . . .
N3 N 0.42879(18) 0.85210(13) 0.06371(14) 0.0144(3) Uani 1 1 d . . .
N4 N 0.26137(18) 1.04708(14) 0.04278(14) 0.0159(3) Uani 1 1 d . . .
H4A H 0.3518 1.0770 0.0137 0.019 Uiso 1 1 calc R . .
H4B H 0.1623 1.0983 0.0496 0.019 Uiso 1 1 calc R . .
N5 N 0.21409(18) 0.22137(14) 0.32718(13) 0.0148(3) Uani 1 1 d . . .
N6 N 0.2216(2) 0.59291(15) 0.53010(14) 0.0195(3) Uani 1 1 d . . .
C1 C 0.5545(2) 0.51890(16) 0.12450(15) 0.0130(3) Uani 1 1 d . . .
C2 C 0.6930(2) 0.42593(17) 0.11245(16) 0.0151(3) Uani 1 1 d . . .
H2 H 0.7962 0.4462 0.0750 0.018 Uiso 1 1 calc R . .
C3 C 0.6775(2) 0.30287(17) 0.15617(16) 0.0162(3) Uani 1 1 d . . .
H3 H 0.7697 0.2376 0.1480 0.019 Uiso 1 1 calc R . .
C4 C 0.5257(2) 0.27581(16) 0.21211(16) 0.0155(3) Uani 1 1 d . . .
H4 H 0.5142 0.1914 0.2449 0.019 Uiso 1 1 calc R . .
C5 C 0.3903(2) 0.37472(16) 0.21938(15) 0.0128(3) Uani 1 1 d . . .
C6 C 0.5624(2) 0.64947(16) 0.08418(15) 0.0135(3) Uani 1 1 d . . .
H6 H 0.6630 0.6753 0.0477 0.016 Uiso 1 1 calc R . .
C7 C 0.2745(2) 0.92405(16) 0.07658(15) 0.0133(3) Uani 1 1 d . . .
C8 C 0.2193(2) 0.35405(16) 0.27599(17) 0.0154(3) Uani 1 1 d . . .
H8A H 0.1954 0.3839 0.3404 0.018 Uiso 1 1 calc R . .
H8B H 0.1264 0.4067 0.2141 0.018 Uiso 1 1 calc R . .
C9 C 0.2553(2) 0.12923(16) 0.44390(16) 0.0156(3) Uani 1 1 d . . .
C10 C 0.2151(2) 0.02171(18) 0.45550(18) 0.0213(4) Uani 1 1 d . . .
H10 H 0.2295 -0.0563 0.5262 0.026 Uiso 1 1 calc R . .
C11 C 0.1489(3) 0.04842(18) 0.34350(19) 0.0233(4) Uani 1 1 d . . .
H11 H 0.1111 -0.0083 0.3244 0.028 Uiso 1 1 calc R . .
C12 C 0.1489(2) 0.17190(18) 0.26686(18) 0.0189(4) Uani 1 1 d . . .
H12 H 0.1100 0.2156 0.1852 0.023 Uiso 1 1 calc R . .
C13 C 0.3340(2) 0.15065(17) 0.53100(17) 0.0175(4) Uani 1 1 d . . .
C14 C 0.3934(3) 0.0783(2) 0.73735(19) 0.0322(5) Uani 1 1 d . . .
H14A H 0.5152 0.0777 0.7212 0.048 Uiso 1 1 calc R . .
H14B H 0.3843 0.0084 0.8158 0.048 Uiso 1 1 calc R . .
H14C H 0.3279 0.1598 0.7382 0.048 Uiso 1 1 calc R . .
C15 C 0.1815(2) 0.63752(18) 0.41557(17) 0.0196(4) Uani 1 1 d . . .
H15 H 0.1317 0.7268 0.3737 0.024 Uiso 1 1 calc R . .
C16 C 0.2014(3) 0.67772(19) 0.58771(18) 0.0240(4) Uani 1 1 d . . .
H16A H 0.3154 0.6826 0.6017 0.036 Uiso 1 1 calc R . .
H16B H 0.1434 0.6448 0.6649 0.036 Uiso 1 1 calc R . .
H16C H 0.1316 0.7630 0.5354 0.036 Uiso 1 1 calc R . .
C17 C 0.3025(4) 0.4586(2) 0.6031(2) 0.0489(8) Uani 1 1 d . . .
H17A H 0.3158 0.4110 0.5544 0.073 Uiso 1 1 calc R . .
H17B H 0.2299 0.4253 0.6724 0.073 Uiso 1 1 calc R . .
H17C H 0.4165 0.4488 0.6315 0.073 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 N2 1.9820(13) . ?
Cu1 N1 2.0912(14) . ?
Cu1 O3 2.1852(13) . ?
Cu1 S1 2.2785(5) . ?
Cu1 Cl1 2.3069(4) . ?
S1 C7 1.7387(17) . ?
O1 C13 1.346(2) . ?
O1 C14 1.451(2) . ?
O2 C13 1.212(2) . ?
O3 C15 1.239(2) . ?
N1 C5 1.339(2) . ?
N1 C1 1.366(2) . ?
N2 C6 1.287(2) . ?
N2 N3 1.3641(19) . ?
N3 C7 1.337(2) . ?
N4 C7 1.335(2) . ?
N4 H4A 0.8800 . ?
N4 H4B 0.8800 . ?
N5 C12 1.364(2) . ?
N5 C9 1.383(2) . ?
N5 C8 1.459(2) . ?
N6 C15 1.315(2) . ?
N6 C16 1.453(2) . ?
N6 C17 1.455(3) . ?
C1 C2 1.386(2) . ?
C1 C6 1.455(2) . ?
C2 C3 1.385(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.390(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.398(2) . ?
C4 H4 0.9500 . ?
C5 C8 1.513(2) . ?
C6 H6 0.9500 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.378(2) . ?
C9 C13 1.459(3) . ?
C10 C11 1.408(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.375(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?

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
N2 Cu1 N1 80.48(6) . . ?
N2 Cu1 O3 114.80(6) . . ?
N1 Cu1 O3 87.55(5) . . ?
N2 Cu1 S1 83.13(4) . . ?
N1 Cu1 S1 163.45(4) . . ?
O3 Cu1 S1 97.27(4) . . ?
N2 Cu1 Cl1 137.78(4) . . ?
N1 Cu1 Cl1 98.97(4) . . ?
O3 Cu1 Cl1 107.32(4) . . ?
S1 Cu1 Cl1 94.701(16) . . ?
C7 S1 Cu1 95.99(6) . . ?
C13 O1 C14 115.00(16) . . ?
C15 O3 Cu1 120.36(12) . . ?
C5 N1 C1 118.17(14) . . ?
C5 N1 Cu1 131.53(11) . . ?
C1 N1 Cu1 110.27(11) . . ?
C6 N2 N3 119.34(14) . . ?
C6 N2 Cu1 115.92(11) . . ?
N3 N2 Cu1 124.43(11) . . ?
C7 N3 N2 111.80(13) . . ?
C7 N4 H4A 120.0 . . ?
C7 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
C12 N5 C9 108.44(14) . . ?
C12 N5 C8 123.44(15) . . ?
C9 N5 C8 127.83(15) . . ?
C15 N6 C16 121.28(16) . . ?
C15 N6 C17 122.28(17) . . ?
C16 N6 C17 116.21(17) . . ?
N1 C1 C2 122.62(15) . . ?
N1 C1 C6 115.45(15) . . ?
C2 C1 C6 121.94(15) . . ?
C3 C2 C1 118.58(15) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C2 C3 C4 119.35(16) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C3 C4 C5 118.98(16) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
N1 C5 C4 122.22(15) . . ?
N1 C5 C8 115.45(14) . . ?
C4 C5 C8 122.32(15) . . ?
N2 C6 C1 117.24(14) . . ?
N2 C6 H6 121.4 . . ?
C1 C6 H6 121.4 . . ?
N4 C7 N3 116.67(15) . . ?
N4 C7 S1 118.71(13) . . ?
N3 C7 S1 124.62(13) . . ?
N5 C8 C5 113.66(14) . . ?
N5 C8 H8A 108.8 . . ?
C5 C8 H8A 108.8 . . ?
N5 C8 H8B 108.8 . . ?
C5 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
C10 C9 N5 107.96(16) . . ?
C10 C9 C13 129.85(17) . . ?
N5 C9 C13 122.14(15) . . ?
C9 C10 C11 107.53(17) . . ?
C9 C10 H10 126.2 . . ?
C11 C10 H10 126.2 . . ?
C12 C11 C10 107.19(17) . . ?
C12 C11 H11 126.4 . . ?
C10 C11 H11 126.4 . . ?
N5 C12 C11 108.88(17) . . ?
N5 C12 H12 125.6 . . ?
C11 C12 H12 125.6 . . ?
O2 C13 O1 123.60(17) . . ?
O2 C13 C9 125.33(17) . . ?
O1 C13 C9 111.08(15) . . ?
O1 C14 H14A 109.5 . . ?
O1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O3 C15 N6 125.84(18) . . ?
O3 C15 H15 117.1 . . ?
N6 C15 H15 117.1 . . ?
N6 C16 H16A 109.5 . . ?
N6 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N6 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N6 C17 H17A 109.5 . . ?
N6 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N6 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 Cu1 S1 C7 1.36(7) . . . . ?
N1 Cu1 S1 C7 9.44(16) . . . . ?
O3 Cu1 S1 C7 115.60(7) . . . . ?
Cl1 Cu1 S1 C7 -136.24(6) . . . . ?
N2 Cu1 O3 C15 65.99(16) . . . . ?
N1 Cu1 O3 C15 144.33(15) . . . . ?
S1 Cu1 O3 C15 -19.78(15) . . . . ?
Cl1 Cu1 O3 C15 -117.04(14) . . . . ?
N2 Cu1 N1 C5 175.78(16) . . . . ?
O3 Cu1 N1 C5 60.13(15) . . . . ?
S1 Cu1 N1 C5 167.65(11) . . . . ?
Cl1 Cu1 N1 C5 -47.02(15) . . . . ?
N2 Cu1 N1 C1 -6.61(11) . . . . ?
O3 Cu1 N1 C1 -122.26(12) . . . . ?
S1 Cu1 N1 C1 -14.7(2) . . . . ?
Cl1 Cu1 N1 C1 130.59(11) . . . . ?
N1 Cu1 N2 C6 7.15(12) . . . . ?
O3 Cu1 N2 C6 89.96(13) . . . . ?
S1 Cu1 N2 C6 -175.18(13) . . . . ?
Cl1 Cu1 N2 C6 -85.74(13) . . . . ?
N1 Cu1 N2 N3 -179.41(14) . . . . ?
O3 Cu1 N2 N3 -96.61(13) . . . . ?
S1 Cu1 N2 N3 -1.74(12) . . . . ?
Cl1 Cu1 N2 N3 87.69(14) . . . . ?
C6 N2 N3 C7 174.47(15) . . . . ?
Cu1 N2 N3 C7 1.2(2) . . . . ?
C5 N1 C1 C2 3.3(2) . . . . ?
Cu1 N1 C1 C2 -174.71(13) . . . . ?
C5 N1 C1 C6 -176.62(15) . . . . ?
Cu1 N1 C1 C6 5.41(18) . . . . ?
N1 C1 C2 C3 -1.7(3) . . . . ?
C6 C1 C2 C3 178.15(16) . . . . ?
C1 C2 C3 C4 -1.0(3) . . . . ?
C2 C3 C4 C5 2.0(3) . . . . ?
C1 N1 C5 C4 -2.1(2) . . . . ?
Cu1 N1 C5 C4 175.32(12) . . . . ?
C1 N1 C5 C8 178.89(15) . . . . ?
Cu1 N1 C5 C8 -3.7(2) . . . . ?
C3 C4 C5 N1 -0.4(3) . . . . ?
C3 C4 C5 C8 178.46(16) . . . . ?
N3 N2 C6 C1 179.90(14) . . . . ?
Cu1 N2 C6 C1 -6.3(2) . . . . ?
N1 C1 C6 N2 0.2(2) . . . . ?
C2 C1 C6 N2 -179.65(16) . . . . ?
N2 N3 C7 N4 -179.49(14) . . . . ?
N2 N3 C7 S1 0.4(2) . . . . ?
Cu1 S1 C7 N4 178.48(13) . . . . ?
Cu1 S1 C7 N3 -1.44(16) . . . . ?
C12 N5 C8 C5 -95.60(19) . . . . ?
C9 N5 C8 C5 91.2(2) . . . . ?
N1 C5 C8 N5 -177.86(14) . . . . ?
C4 C5 C8 N5 3.2(2) . . . . ?
C12 N5 C9 C10 0.0(2) . . . . ?
C8 N5 C9 C10 174.01(16) . . . . ?
C12 N5 C9 C13 177.82(16) . . . . ?
C8 N5 C9 C13 -8.2(3) . . . . ?
N5 C9 C10 C11 0.3(2) . . . . ?
C13 C9 C10 C11 -177.25(18) . . . . ?
C9 C10 C11 C12 -0.5(2) . . . . ?
C9 N5 C12 C11 -0.4(2) . . . . ?
C8 N5 C12 C11 -174.67(15) . . . . ?
C10 C11 C12 N5 0.6(2) . . . . ?
C14 O1 C13 O2 1.6(3) . . . . ?
C14 O1 C13 C9 -177.96(16) . . . . ?
C10 C9 C13 O2 162.75(19) . . . . ?
N5 C9 C13 O2 -14.5(3) . . . . ?
C10 C9 C13 O1 -17.7(3) . . . . ?
N5 C9 C13 O1 165.08(15) . . . . ?
Cu1 O3 C15 N6 -157.23(15) . . . . ?
C16 N6 C15 O3 175.92(18) . . . . ?
C17 N6 C15 O3 1.6(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        30.14
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.488
_refine_diff_density_min         -0.521
_refine_diff_density_rms         0.081
####################################################################### 
# 
# 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_feba246
_database_code_depnum_ccdc_archive 'CCDC 1052908'
_audit_update_record             
;
2015-03-09 deposited with the CCDC.
2015-04-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H24 Cl Cu N6 S, Cl, 2(H2 O)'
_chemical_formula_sum            'C15 H28 Cl2 Cu N6 O2 S'
_chemical_formula_weight         490.93

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'
S S 0.1246 0.1234 '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
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   7.6629(3)
_cell_length_b                   11.7864(3)
_cell_length_c                   13.0949(4)
_cell_angle_alpha                72.1141(11)
_cell_angle_beta                 73.6132(12)
_cell_angle_gamma                74.3107(11)
_cell_volume                     1057.72(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9915
_cell_measurement_theta_min      2.79
_cell_measurement_theta_max      30.09

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             510
_exptl_absorpt_coefficient_mu    1.407
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7939
_exptl_absorpt_correction_T_max  0.9524
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            26580
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_sigmaI/netI    0.0248
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.17
_diffrn_reflns_theta_max         30.11
_reflns_number_total             6217
_reflns_number_gt                5482
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0445P)²+0.8120P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6217
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0303
_refine_ls_wR_factor_ref         0.0832
_refine_ls_wR_factor_gt          0.0802
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.002
_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 0.84775(3) 0.287036(16) 0.559592(15) 0.01130(6) Uani 1 1 d . . .
S1 S 1.09358(5) 0.24622(3) 0.42178(3) 0.01438(8) Uani 1 1 d . . .
Cl1 Cl 0.62155(5) 0.19364(3) 0.53442(3) 0.01476(8) Uani 1 1 d . . .
C7 C 1.0386(2) 0.38853(14) 0.32982(13) 0.0133(3) Uani 1 1 d . . .
N1 N 0.67548(18) 0.37539(12) 0.66390(11) 0.0129(2) Uani 1 1 d . . .
N2 N 0.83012(18) 0.45657(12) 0.46576(11) 0.0124(2) Uani 1 1 d . . .
N3 N 0.92121(19) 0.48555(12) 0.35926(11) 0.0142(3) Uani 1 1 d . . .
N4 N 1.1214(2) 0.40382(13) 0.22250(11) 0.0174(3) Uani 1 1 d . . .
C5 C 0.6220(2) 0.49661(14) 0.62431(13) 0.0136(3) Uani 1 1 d . . .
C6 C 0.7131(2) 0.53986(14) 0.50981(13) 0.0139(3) Uani 1 1 d . . .
H6 H 0.6885 0.6228 0.4705 0.017 Uiso 1 1 calc R . .
N5 N 0.86002(18) 0.14946(12) 0.72040(11) 0.0120(2) Uani 1 1 d . . .
C14 C 0.8900(2) 0.02072(14) 0.71746(13) 0.0143(3) Uani 1 1 d . . .
H14A H 0.7996 0.0127 0.6803 0.017 Uiso 1 1 calc R . .
H14B H 0.8679 -0.0308 0.7936 0.017 Uiso 1 1 calc R . .
C2 C 0.4766(2) 0.38232(16) 0.83792(14) 0.0194(3) Uani 1 1 d . . .
H2 H 0.4286 0.3419 0.9115 0.023 Uiso 1 1 calc R . .
C11 C 0.9985(2) 0.16152(15) 0.77429(13) 0.0154(3) Uani 1 1 d . . .
H11A H 0.9768 0.1138 0.8518 0.018 Uiso 1 1 calc R . .
H11B H 0.9818 0.2479 0.7738 0.018 Uiso 1 1 calc R . .
C4 C 0.4914(2) 0.56593(15) 0.69080(14) 0.0177(3) Uani 1 1 d . . .
H4 H 0.4518 0.6510 0.6633 0.021 Uiso 1 1 calc R . .
C3 C 0.4201(2) 0.50741(16) 0.79898(15) 0.0205(3) Uani 1 1 d . . .
H3 H 0.3324 0.5532 0.8464 0.025 Uiso 1 1 calc R . .
C9 C 1.2563(3) 0.30894(17) 0.17654(15) 0.0226(4) Uani 1 1 d . . .
H9A H 1.2724 0.2339 0.2349 0.034 Uiso 1 1 calc R . .
H9B H 1.3754 0.3349 0.1443 0.034 Uiso 1 1 calc R . .
H9C H 1.2117 0.2941 0.1195 0.034 Uiso 1 1 calc R . .
C10 C 0.6705(2) 0.18203(15) 0.78896(13) 0.0158(3) Uani 1 1 d . . .
H10A H 0.6734 0.1482 0.8678 0.019 Uiso 1 1 calc R . .
H10B H 0.5824 0.1458 0.7725 0.019 Uiso 1 1 calc R . .
C1 C 0.6054(2) 0.31798(14) 0.76612(13) 0.0144(3) Uani 1 1 d . . .
C8 C 1.0814(3) 0.52065(16) 0.14312(14) 0.0220(3) Uani 1 1 d . . .
H8A H 1.1792 0.5660 0.1293 0.033 Uiso 1 1 calc R . .
H8B H 0.9614 0.5678 0.1728 0.033 Uiso 1 1 calc R . .
H8C H 1.0769 0.5063 0.0741 0.033 Uiso 1 1 calc R . .
Cl2 Cl 0.15749(7) 0.78194(4) 0.92472(4) 0.02814(11) Uani 1 1 d . . .
N6 N 1.22263(18) -0.01242(12) 0.71395(11) 0.0126(2) Uani 1 1 d . . .
H6A H 1.1991 -0.0589 0.7861 0.015 Uiso 1 1 calc R . .
C13 C 1.0851(2) -0.02375(14) 0.65751(13) 0.0136(3) Uani 1 1 d . . .
H13A H 1.1011 -0.1098 0.6571 0.016 Uiso 1 1 calc R . .
H13B H 1.1066 0.0252 0.5804 0.016 Uiso 1 1 calc R . .
C12 C 1.1952(2) 0.11750(14) 0.71676(13) 0.0144(3) Uani 1 1 d . . .
H12A H 1.2206 0.1690 0.6408 0.017 Uiso 1 1 calc R . .
H12B H 1.2834 0.1245 0.7560 0.017 Uiso 1 1 calc R . .
C15 C 1.4178(2) -0.05887(15) 0.66112(14) 0.0168(3) Uani 1 1 d . . .
H15A H 1.4501 -0.0060 0.5874 0.025 Uiso 1 1 calc R . .
H15B H 1.4299 -0.1418 0.6555 0.025 Uiso 1 1 calc R . .
H15C H 1.5016 -0.0594 0.7057 0.025 Uiso 1 1 calc R . .
O1 O 0.2588(2) 0.13937(14) 0.97244(12) 0.0311(3) Uani 1 1 d G . .
H1A H 0.1423 0.1663 0.9988 0.047 Uiso 1 1 d G . .
H1B H 0.3255 0.1403 1.0160 0.047 Uiso 1 1 d G . .
O2 O 0.4540(2) 0.92353(17) 0.91176(13) 0.0384(4) Uani 1 1 d G . .
H2A H 0.3969 0.9815 0.9447 0.058 Uiso 1 1 d G . .
H2B H 0.3869 0.8685 0.9312 0.058 Uiso 1 1 d G . .


_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 1.9508(13) . ?
Cu1 N2 1.9901(13) . ?
Cu1 N5 2.2370(13) . ?
Cu1 S1 2.2719(4) . ?
Cu1 Cl1 2.4295(4) . ?
S1 C7 1.7620(16) . ?
C7 N3 1.336(2) . ?
C7 N4 1.346(2) . ?
N1 C1 1.331(2) . ?
N1 C5 1.351(2) . ?
N2 C6 1.296(2) . ?
N2 N3 1.3549(18) . ?
N4 C9 1.455(2) . ?
N4 C8 1.464(2) . ?
C5 C4 1.389(2) . ?
C5 C6 1.459(2) . ?
C6 H6 0.9500 . ?
N5 C14 1.483(2) . ?
N5 C11 1.487(2) . ?
N5 C10 1.496(2) . ?
C14 C13 1.514(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C2 C3 1.392(2) . ?
C2 C1 1.394(2) . ?
C2 H2 0.9500 . ?
C11 C12 1.512(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C4 C3 1.396(2) . ?
C4 H4 0.9500 . ?
C3 H3 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C1 1.504(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
N6 C15 1.490(2) . ?
N6 C12 1.499(2) . ?
N6 C13 1.5001(19) . ?
N6 H6A 0.9300 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
O1 H1A 0.8700 . ?
O1 H1B 0.8705 . ?
O2 H2A 0.8696 . ?
O2 H2B 0.8693 . ?

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 79.91(6) . . ?
N1 Cu1 N5 77.91(5) . . ?
N2 Cu1 N5 152.23(5) . . ?
N1 Cu1 S1 158.77(4) . . ?
N2 Cu1 S1 83.31(4) . . ?
N5 Cu1 S1 113.45(4) . . ?
N1 Cu1 Cl1 96.25(4) . . ?
N2 Cu1 Cl1 109.71(4) . . ?
N5 Cu1 Cl1 89.22(4) . . ?
S1 Cu1 Cl1 101.600(15) . . ?
C7 S1 Cu1 94.37(5) . . ?
N3 C7 N4 116.43(14) . . ?
N3 C7 S1 124.41(12) . . ?
N4 C7 S1 119.15(12) . . ?
C1 N1 C5 122.03(14) . . ?
C1 N1 Cu1 121.62(11) . . ?
C5 N1 Cu1 116.20(11) . . ?
C6 N2 N3 120.30(13) . . ?
C6 N2 Cu1 115.87(11) . . ?
N3 N2 Cu1 123.62(10) . . ?
C7 N3 N2 111.44(13) . . ?
C7 N4 C9 123.80(14) . . ?
C7 N4 C8 121.15(14) . . ?
C9 N4 C8 115.05(14) . . ?
N1 C5 C4 120.28(15) . . ?
N1 C5 C6 112.83(14) . . ?
C4 C5 C6 126.89(15) . . ?
N2 C6 C5 114.95(14) . . ?
N2 C6 H6 122.5 . . ?
C5 C6 H6 122.5 . . ?
C14 N5 C11 109.11(12) . . ?
C14 N5 C10 107.85(12) . . ?
C11 N5 C10 108.25(12) . . ?
C14 N5 Cu1 115.64(10) . . ?
C11 N5 Cu1 112.70(10) . . ?
C10 N5 Cu1 102.78(9) . . ?
N5 C14 C13 111.63(12) . . ?
N5 C14 H14A 109.3 . . ?
C13 C14 H14A 109.3 . . ?
N5 C14 H14B 109.3 . . ?
C13 C14 H14B 109.3 . . ?
H14A C14 H14B 108.0 . . ?
C3 C2 C1 118.22(16) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
N5 C11 C12 111.74(13) . . ?
N5 C11 H11A 109.3 . . ?
C12 C11 H11A 109.3 . . ?
N5 C11 H11B 109.3 . . ?
C12 C11 H11B 109.3 . . ?
H11A C11 H11B 107.9 . . ?
C5 C4 C3 118.31(15) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
C2 C3 C4 120.44(15) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
N4 C9 H9A 109.5 . . ?
N4 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N4 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N5 C10 C1 110.64(13) . . ?
N5 C10 H10A 109.5 . . ?
C1 C10 H10A 109.5 . . ?
N5 C10 H10B 109.5 . . ?
C1 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
N1 C1 C2 120.68(15) . . ?
N1 C1 C10 112.93(14) . . ?
C2 C1 C10 126.27(15) . . ?
N4 C8 H8A 109.5 . . ?
N4 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N4 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C15 N6 C12 111.07(12) . . ?
C15 N6 C13 112.15(12) . . ?
C12 N6 C13 109.62(12) . . ?
C15 N6 H6A 108.0 . . ?
C12 N6 H6A 108.0 . . ?
C13 N6 H6A 108.0 . . ?
N6 C13 C14 109.47(12) . . ?
N6 C13 H13A 109.8 . . ?
C14 C13 H13A 109.8 . . ?
N6 C13 H13B 109.8 . . ?
C14 C13 H13B 109.8 . . ?
H13A C13 H13B 108.2 . . ?
N6 C12 C11 110.29(13) . . ?
N6 C12 H12A 109.6 . . ?
C11 C12 H12A 109.6 . . ?
N6 C12 H12B 109.6 . . ?
C11 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
N6 C15 H15A 109.5 . . ?
N6 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N6 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
H1A O1 H1B 109.4 . . ?
H2A O2 H2B 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 Cu1 S1 C7 -50.51(13) . . . . ?
N2 Cu1 S1 C7 -12.64(6) . . . . ?
N5 Cu1 S1 C7 -169.59(6) . . . . ?
Cl1 Cu1 S1 C7 96.17(5) . . . . ?
Cu1 S1 C7 N3 16.03(14) . . . . ?
Cu1 S1 C7 N4 -165.39(12) . . . . ?
N2 Cu1 N1 C1 179.60(13) . . . . ?
N5 Cu1 N1 C1 -17.22(12) . . . . ?
S1 Cu1 N1 C1 -142.14(11) . . . . ?
Cl1 Cu1 N1 C1 70.64(12) . . . . ?
N2 Cu1 N1 C5 3.96(11) . . . . ?
N5 Cu1 N1 C5 167.14(12) . . . . ?
S1 Cu1 N1 C5 42.22(19) . . . . ?
Cl1 Cu1 N1 C5 -105.01(11) . . . . ?
N1 Cu1 N2 C6 -4.40(12) . . . . ?
N5 Cu1 N2 C6 -41.79(18) . . . . ?
S1 Cu1 N2 C6 -171.35(12) . . . . ?
Cl1 Cu1 N2 C6 88.68(12) . . . . ?
N1 Cu1 N2 N3 -179.21(13) . . . . ?
N5 Cu1 N2 N3 143.40(11) . . . . ?
S1 Cu1 N2 N3 13.84(11) . . . . ?
Cl1 Cu1 N2 N3 -86.12(12) . . . . ?
N4 C7 N3 N2 172.88(13) . . . . ?
S1 C7 N3 N2 -8.50(19) . . . . ?
C6 N2 N3 C7 178.46(14) . . . . ?
Cu1 N2 N3 C7 -6.96(18) . . . . ?
N3 C7 N4 C9 178.47(15) . . . . ?
S1 C7 N4 C9 -0.2(2) . . . . ?
N3 C7 N4 C8 -0.8(2) . . . . ?
S1 C7 N4 C8 -179.48(13) . . . . ?
C1 N1 C5 C4 0.7(2) . . . . ?
Cu1 N1 C5 C4 176.30(12) . . . . ?
C1 N1 C5 C6 -178.63(14) . . . . ?
Cu1 N1 C5 C6 -3.00(17) . . . . ?
N3 N2 C6 C5 179.01(13) . . . . ?
Cu1 N2 C6 C5 4.02(18) . . . . ?
N1 C5 C6 N2 -0.7(2) . . . . ?
C4 C5 C6 N2 -179.96(16) . . . . ?
N1 Cu1 N5 C14 146.96(11) . . . . ?
N2 Cu1 N5 C14 -175.35(11) . . . . ?
S1 Cu1 N5 C14 -51.92(11) . . . . ?
Cl1 Cu1 N5 C14 50.39(10) . . . . ?
N1 Cu1 N5 C11 -86.57(10) . . . . ?
N2 Cu1 N5 C11 -48.88(16) . . . . ?
S1 Cu1 N5 C11 74.55(10) . . . . ?
Cl1 Cu1 N5 C11 176.86(9) . . . . ?
N1 Cu1 N5 C10 29.73(9) . . . . ?
N2 Cu1 N5 C10 67.42(15) . . . . ?
S1 Cu1 N5 C10 -169.15(8) . . . . ?
Cl1 Cu1 N5 C10 -66.84(9) . . . . ?
C11 N5 C14 C13 -57.87(16) . . . . ?
C10 N5 C14 C13 -175.25(12) . . . . ?
Cu1 N5 C14 C13 70.39(14) . . . . ?
C14 N5 C11 C12 56.85(17) . . . . ?
C10 N5 C11 C12 173.98(13) . . . . ?
Cu1 N5 C11 C12 -73.04(14) . . . . ?
N1 C5 C4 C3 0.9(2) . . . . ?
C6 C5 C4 C3 -179.94(16) . . . . ?
C1 C2 C3 C4 0.0(3) . . . . ?
C5 C4 C3 C2 -1.2(3) . . . . ?
C14 N5 C10 C1 -161.33(13) . . . . ?
C11 N5 C10 C1 80.73(16) . . . . ?
Cu1 N5 C10 C1 -38.71(14) . . . . ?
C5 N1 C1 C2 -1.9(2) . . . . ?
Cu1 N1 C1 C2 -177.31(12) . . . . ?
C5 N1 C1 C10 174.31(14) . . . . ?
Cu1 N1 C1 C10 -1.08(19) . . . . ?
C3 C2 C1 N1 1.6(3) . . . . ?
C3 C2 C1 C10 -174.13(16) . . . . ?
N5 C10 C1 N1 29.62(19) . . . . ?
N5 C10 C1 C2 -154.40(16) . . . . ?
C15 N6 C13 C14 178.01(13) . . . . ?
C12 N6 C13 C14 -58.14(16) . . . . ?
N5 C14 C13 N6 59.29(16) . . . . ?
C15 N6 C12 C11 -177.94(12) . . . . ?
C13 N6 C12 C11 57.57(16) . . . . ?
N5 C11 C12 N6 -57.59(17) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2B Cl2 0.87 2.29 3.1042(17) 156.0 .

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        30.11
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.994
_refine_diff_density_min         -0.765
_refine_diff_density_rms         0.085
####################################################################### 
# 
# 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_feba265
_database_code_depnum_ccdc_archive 'CCDC 1052909'
_audit_update_record             
;
2015-03-09 deposited with the CCDC.
2015-04-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H20 Cl Cu N5 O S, 0.925(C H4 O)'
_chemical_formula_sum            'C14.93 H23.70 Cl Cu N5 O1.92 S'
_chemical_formula_weight         435.04

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'
S S 0.1246 0.1234 '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
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.8676(7)
_cell_length_b                   12.0982(8)
_cell_length_c                   16.6060(10)
_cell_angle_alpha                86.450(3)
_cell_angle_beta                 74.015(3)
_cell_angle_gamma                77.176(3)
_cell_volume                     1858.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9524
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      30.17

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.40
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.555
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             903
_exptl_absorpt_coefficient_mu    1.450
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5309
_exptl_absorpt_correction_T_max  0.5947
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            42308
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_av_sigmaI/netI    0.0252
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.20
_diffrn_reflns_theta_max         25.00
_reflns_number_total             6537
_reflns_number_gt                6388
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0208P)²+2.4001P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6537
_refine_ls_number_parameters     465
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0285
_refine_ls_R_factor_gt           0.0279
_refine_ls_wR_factor_ref         0.0683
_refine_ls_wR_factor_gt          0.0680
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.097
_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
Cu1A Cu 0.08049(3) 0.46740(2) 0.657079(15) 0.01384(7) Uani 1 1 d . . .
Cl1A Cl -0.03756(6) 0.49920(4) 0.81064(3) 0.02272(12) Uani 1 1 d . . .
S1A S 0.14141(6) 0.63379(4) 0.61223(3) 0.01680(12) Uani 1 1 d . . .
O1A O 0.52621(16) 0.41679(13) 0.60370(10) 0.0242(4) Uani 1 1 d . . .
N1A N 0.00878(18) 0.33018(14) 0.65917(11) 0.0148(4) Uani 1 1 d . . .
N2A N -0.08193(18) 0.52399(14) 0.60521(11) 0.0144(4) Uani 1 1 d . . .
N3A N -0.11465(18) 0.63183(14) 0.57712(11) 0.0151(4) Uani 1 1 d . . .
N4A N -0.04422(19) 0.80141(15) 0.56367(11) 0.0172(4) Uani 1 1 d . . .
N5A N 0.26006(18) 0.34407(14) 0.67777(11) 0.0150(4) Uani 1 1 d . . .
C1A C 0.0671(2) 0.23728(17) 0.69477(13) 0.0161(4) Uani 1 1 d . . .
C2A C 0.0038(2) 0.14355(18) 0.70797(14) 0.0195(5) Uani 1 1 d . . .
H2A H 0.0460 0.0759 0.7320 0.023 Uiso 1 1 calc R . .
C3A C -0.1231(2) 0.15177(18) 0.68494(14) 0.0216(5) Uani 1 1 d . . .
H3A H -0.1694 0.0893 0.6942 0.026 Uiso 1 1 calc R . .
C4A C -0.1837(2) 0.25058(18) 0.64830(14) 0.0190(4) Uani 1 1 d . . .
H4A H -0.2702 0.2561 0.6322 0.023 Uiso 1 1 calc R . .
C5A C -0.1141(2) 0.34034(18) 0.63600(13) 0.0157(4) Uani 1 1 d . . .
C6A C -0.1606(2) 0.45273(18) 0.60267(13) 0.0161(4) Uani 1 1 d . . .
H6A H -0.2423 0.4719 0.5808 0.019 Uiso 1 1 calc R . .
C7A C -0.0176(2) 0.69027(17) 0.58268(12) 0.0146(4) Uani 1 1 d . . .
C8A C -0.1672(2) 0.85365(18) 0.53134(14) 0.0207(5) Uani 1 1 d . . .
H8AA H -0.2339 0.8022 0.5401 0.031 Uiso 1 1 calc R . .
H8AB H -0.1330 0.8688 0.4713 0.031 Uiso 1 1 calc R . .
H8AC H -0.2171 0.9251 0.5609 0.031 Uiso 1 1 calc R . .
C9A C 0.0545(3) 0.87376(18) 0.56559(15) 0.0235(5) Uani 1 1 d . . .
H9AA H 0.1316 0.8654 0.5131 0.035 Uiso 1 1 calc R . .
H9AB H 0.0967 0.8517 0.6127 0.035 Uiso 1 1 calc R . .
H9AC H 0.0019 0.9529 0.5723 0.035 Uiso 1 1 calc R . .
C10A C 0.1939(2) 0.25087(17) 0.72368(14) 0.0174(4) Uani 1 1 d . . .
H10A H 0.1621 0.2675 0.7845 0.021 Uiso 1 1 calc R . .
H10B H 0.2672 0.1789 0.7147 0.021 Uiso 1 1 calc R . .
C11A C 0.3602(2) 0.30002(18) 0.59595(13) 0.0179(4) Uani 1 1 d . . .
H11A H 0.3041 0.2812 0.5596 0.021 Uiso 1 1 calc R . .
H11B H 0.4276 0.2298 0.6054 0.021 Uiso 1 1 calc R . .
C12A C 0.4449(2) 0.38702(19) 0.55274(14) 0.0208(5) Uani 1 1 d . . .
H12A H 0.5111 0.3559 0.4988 0.025 Uiso 1 1 calc R . .
H12B H 0.3777 0.4557 0.5406 0.025 Uiso 1 1 calc R . .
C13A C 0.4323(2) 0.46217(19) 0.68143(15) 0.0238(5) Uani 1 1 d . . .
H13A H 0.3654 0.5321 0.6707 0.029 Uiso 1 1 calc R . .
H13B H 0.4901 0.4829 0.7160 0.029 Uiso 1 1 calc R . .
C14A C 0.3460(2) 0.37894(19) 0.72906(14) 0.0199(5) Uani 1 1 d . . .
H14A H 0.4121 0.3113 0.7436 0.024 Uiso 1 1 calc R . .
H14B H 0.2803 0.4142 0.7818 0.024 Uiso 1 1 calc R . .
Cu1B Cu 0.50001(3) 0.03137(2) 0.162333(16) 0.01468(7) Uani 1 1 d . . .
Cl1B Cl 0.43904(6) -0.04244(4) 0.30648(3) 0.01940(12) Uani 1 1 d . . .
S1B S 0.74368(6) -0.03660(4) 0.11834(3) 0.01848(12) Uani 1 1 d . . .
O1B O 0.69385(18) 0.30395(14) 0.16749(11) 0.0288(4) Uani 1 1 d . . .
N1B N 0.30216(19) 0.07513(15) 0.15296(11) 0.0160(4) Uani 1 1 d . . .
N2B N 0.49684(19) -0.09454(15) 0.09067(11) 0.0171(4) Uani 1 1 d . . .
N3B N 0.6110(2) -0.18005(15) 0.06075(11) 0.0201(4) Uani 1 1 d . . .
N4B N 0.8494(2) -0.24573(16) 0.05305(12) 0.0241(4) Uani 1 1 d . . .
N5B N 0.44043(19) 0.20865(15) 0.20283(11) 0.0170(4) Uani 1 1 d . . .
C1B C 0.2138(2) 0.16936(18) 0.18829(13) 0.0179(4) Uani 1 1 d . . .
C2B C 0.0726(2) 0.19844(19) 0.18267(14) 0.0221(5) Uani 1 1 d . . .
H2B H 0.0096 0.2665 0.2070 0.027 Uiso 1 1 calc R . .
C3B C 0.0264(2) 0.1253(2) 0.14061(14) 0.0239(5) Uani 1 1 d . . .
H3B H -0.0701 0.1429 0.1363 0.029 Uiso 1 1 calc R . .
C4B C 0.1191(2) 0.0262(2) 0.10451(14) 0.0226(5) Uani 1 1 d . . .
H4B H 0.0871 -0.0243 0.0759 0.027 Uiso 1 1 calc R . .
C5B C 0.2592(2) 0.00328(18) 0.11136(13) 0.0179(4) Uani 1 1 d . . .
C6B C 0.3737(2) -0.09342(18) 0.07720(14) 0.0196(5) Uani 1 1 d . . .
H6B H 0.3590 -0.1519 0.0470 0.024 Uiso 1 1 calc R . .
C7B C 0.7313(2) -0.16169(18) 0.07493(13) 0.0186(4) Uani 1 1 d . . .
C8B C 0.8433(3) -0.3526(2) 0.01896(16) 0.0326(6) Uani 1 1 d . . .
H8BA H 0.7424 -0.3583 0.0295 0.049 Uiso 1 1 calc R . .
H8BB H 0.8947 -0.4162 0.0461 0.049 Uiso 1 1 calc R . .
H8BC H 0.8888 -0.3550 -0.0415 0.049 Uiso 1 1 calc R . .
C9B C 0.9915(3) -0.2352(2) 0.05609(17) 0.0315(6) Uani 1 1 d . . .
H9BA H 1.0412 -0.2053 0.0026 0.047 Uiso 1 1 calc R . .
H9BB H 1.0474 -0.3098 0.0664 0.047 Uiso 1 1 calc R . .
H9BC H 0.9818 -0.1832 0.1013 0.047 Uiso 1 1 calc R . .
C10B C 0.2806(2) 0.23165(18) 0.23674(14) 0.0196(5) Uani 1 1 d . . .
H10C H 0.2409 0.3141 0.2341 0.024 Uiso 1 1 calc R . .
H10D H 0.2556 0.2081 0.2962 0.024 Uiso 1 1 calc R . .
C11B C 0.4790(2) 0.28419(18) 0.12945(14) 0.0214(5) Uani 1 1 d . . .
H11C H 0.4289 0.3635 0.1448 0.026 Uiso 1 1 calc R . .
H11D H 0.4467 0.2619 0.0826 0.026 Uiso 1 1 calc R . .
C12B C 0.6401(3) 0.2763(2) 0.10172(15) 0.0248(5) Uani 1 1 d . . .
H12C H 0.6892 0.1983 0.0820 0.030 Uiso 1 1 calc R . .
H12D H 0.6628 0.3287 0.0541 0.030 Uiso 1 1 calc R . .
C13B C 0.6599(3) 0.2310(2) 0.23758(15) 0.0239(5) Uani 1 1 d . . .
H13C H 0.6967 0.2518 0.2830 0.029 Uiso 1 1 calc R . .
H13D H 0.7085 0.1517 0.2210 0.029 Uiso 1 1 calc R . .
C14B C 0.4994(2) 0.23890(19) 0.26959(14) 0.0212(5) Uani 1 1 d . . .
H14C H 0.4796 0.1870 0.3178 0.025 Uiso 1 1 calc R . .
H14D H 0.4510 0.3171 0.2891 0.025 Uiso 1 1 calc R . .
O3A O 0.3170(7) 0.5684(5) 0.0788(4) 0.0562(15) Uiso 0.40 1 d PD A 1
H3AA H 0.2553 0.5302 0.1020 0.084 Uiso 0.40 1 calc PR A 1
C16A C 0.3513(14) 0.6257(10) 0.1421(7) 0.050(3) Uiso 0.40 1 d PD A 1
H16A H 0.4437 0.6483 0.1184 0.075 Uiso 0.40 1 calc PR A 1
H16B H 0.3583 0.5744 0.1896 0.075 Uiso 0.40 1 calc PR A 1
H16C H 0.2753 0.6932 0.1613 0.075 Uiso 0.40 1 calc PR A 1
O3B O 0.2721(5) 0.6555(4) 0.1101(3) 0.0325(11) Uiso 0.35 1 d PD B 2
H3BA H 0.2045 0.6242 0.1356 0.049 Uiso 0.35 1 calc PRD B 2
C16B C 0.3892(9) 0.6125(7) 0.1374(5) 0.051(2) Uiso 0.35 1 d PD B 2
H16D H 0.4719 0.5860 0.0894 0.076 Uiso 0.35 1 calc PR B 2
H16E H 0.3711 0.5488 0.1752 0.076 Uiso 0.35 1 calc PR B 2
H16F H 0.4100 0.6713 0.1673 0.076 Uiso 0.35 1 calc PR B 2
O3C O 0.3226(8) 0.5478(6) 0.2014(4) 0.0327(16) Uiso 0.25 1 d PD C 3
H3C H 0.2517 0.5314 0.1899 0.049 Uiso 0.25 1 calc PR C 3
C16C C 0.3892(9) 0.6125(7) 0.1374(5) 0.051(2) Uiso 0.25 1 d PD C 3
H16G H 0.3463 0.6930 0.1490 0.076 Uiso 0.25 1 calc PR C 3
H16H H 0.3758 0.5922 0.0843 0.076 Uiso 0.25 1 calc PR C 3
H16I H 0.4925 0.5982 0.1335 0.076 Uiso 0.25 1 calc PR C 3
O2 O 0.6744(2) 0.01614(19) 0.38632(14) 0.0352(5) Uani 0.85 1 d P . .
H2 H 0.6196 0.0005 0.3600 0.053 Uiso 0.85 1 calc PR . .
C15 C 0.5945(3) 0.0954(3) 0.4492(2) 0.0375(8) Uani 0.85 1 d P . .
H15A H 0.6083 0.1713 0.4300 0.056 Uiso 0.85 1 calc PR . .
H15B H 0.6275 0.0764 0.4999 0.056 Uiso 0.85 1 calc PR . .
H15C H 0.4920 0.0937 0.4617 0.056 Uiso 0.85 1 calc PR . .


_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
Cu1A N1A 1.9388(17) . ?
Cu1A N2A 1.9948(17) . ?
Cu1A N5A 2.1406(17) . ?
Cu1A S1A 2.2523(6) . ?
Cu1A Cl1A 2.5088(6) . ?
S1A C7A 1.754(2) . ?
O1A C12A 1.424(3) . ?
O1A C13A 1.425(3) . ?
N1A C1A 1.327(3) . ?
N1A C5A 1.349(3) . ?
N2A C6A 1.291(3) . ?
N2A N3A 1.358(2) . ?
N3A C7A 1.335(3) . ?
N4A C7A 1.346(3) . ?
N4A C9A 1.455(3) . ?
N4A C8A 1.462(3) . ?
N5A C11A 1.491(3) . ?
N5A C14A 1.491(3) . ?
N5A C10A 1.492(3) . ?
C1A C2A 1.391(3) . ?
C1A C10A 1.502(3) . ?
C2A C3A 1.388(3) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.396(3) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.385(3) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.461(3) . ?
C6A H6A 0.9500 . ?
C8A H8AA 0.9800 . ?
C8A H8AB 0.9800 . ?
C8A H8AC 0.9800 . ?
C9A H9AA 0.9800 . ?
C9A H9AB 0.9800 . ?
C9A H9AC 0.9800 . ?
C10A H10A 0.9900 . ?
C10A H10B 0.9900 . ?
C11A C12A 1.513(3) . ?
C11A H11A 0.9900 . ?
C11A H11B 0.9900 . ?
C12A H12A 0.9900 . ?
C12A H12B 0.9900 . ?
C13A C14A 1.508(3) . ?
C13A H13A 0.9900 . ?
C13A H13B 0.9900 . ?
C14A H14A 0.9900 . ?
C14A H14B 0.9900 . ?
Cu1B N1B 1.9530(18) . ?
Cu1B N2B 2.0009(18) . ?
Cu1B N5B 2.1907(18) . ?
Cu1B S1B 2.2848(6) . ?
Cu1B Cl1B 2.4636(6) . ?
S1B C7B 1.758(2) . ?
O1B C12B 1.425(3) . ?
O1B C13B 1.427(3) . ?
N1B C1B 1.328(3) . ?
N1B C5B 1.346(3) . ?
N2B C6B 1.292(3) . ?
N2B N3B 1.351(2) . ?
N3B C7B 1.339(3) . ?
N4B C7B 1.346(3) . ?
N4B C9B 1.450(3) . ?
N4B C8B 1.463(3) . ?
N5B C14B 1.484(3) . ?
N5B C10B 1.489(3) . ?
N5B C11B 1.492(3) . ?
C1B C2B 1.387(3) . ?
C1B C10B 1.496(3) . ?
C2B C3B 1.382(3) . ?
C2B H2B 0.9500 . ?
C3B C4B 1.390(3) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.383(3) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.452(3) . ?
C6B H6B 0.9500 . ?
C8B H8BA 0.9800 . ?
C8B H8BB 0.9800 . ?
C8B H8BC 0.9800 . ?
C9B H9BA 0.9800 . ?
C9B H9BB 0.9800 . ?
C9B H9BC 0.9800 . ?
C10B H10C 0.9900 . ?
C10B H10D 0.9900 . ?
C11B C12B 1.511(3) . ?
C11B H11C 0.9900 . ?
C11B H11D 0.9900 . ?
C12B H12C 0.9900 . ?
C12B H12D 0.9900 . ?
C13B C14B 1.508(3) . ?
C13B H13C 0.9900 . ?
C13B H13D 0.9900 . ?
C14B H14C 0.9900 . ?
C14B H14D 0.9900 . ?
O3A C16A 1.445(11) . ?
O3A H3AA 0.8400 . ?
C16A H16A 0.9800 . ?
C16A H16B 0.9800 . ?
C16A H16C 0.9800 . ?
O3B C16B 1.342(8) . ?
O3B H3BA 0.8400 . ?
C16B H16D 0.9800 . ?
C16B H16E 0.9800 . ?
C16B H16F 0.9800 . ?
O3C H3C 0.8400 . ?
O2 C15 1.402(4) . ?
O2 H2 0.8400 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

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
N1A Cu1A N2A 79.68(7) . . ?
N1A Cu1A N5A 79.90(7) . . ?
N2A Cu1A N5A 153.91(7) . . ?
N1A Cu1A S1A 159.83(5) . . ?
N2A Cu1A S1A 83.88(5) . . ?
N5A Cu1A S1A 111.88(5) . . ?
N1A Cu1A Cl1A 91.49(5) . . ?
N2A Cu1A Cl1A 103.19(5) . . ?
N5A Cu1A Cl1A 93.40(5) . . ?
S1A Cu1A Cl1A 103.65(2) . . ?
C7A S1A Cu1A 94.87(7) . . ?
C12A O1A C13A 110.09(16) . . ?
C1A N1A C5A 122.92(18) . . ?
C1A N1A Cu1A 119.58(14) . . ?
C5A N1A Cu1A 116.61(14) . . ?
C6A N2A N3A 120.60(17) . . ?
C6A N2A Cu1A 115.92(14) . . ?
N3A N2A Cu1A 123.42(13) . . ?
C7A N3A N2A 111.10(16) . . ?
C7A N4A C9A 122.41(18) . . ?
C7A N4A C8A 121.42(18) . . ?
C9A N4A C8A 115.87(17) . . ?
C11A N5A C14A 108.39(16) . . ?
C11A N5A C10A 109.11(16) . . ?
C14A N5A C10A 107.46(16) . . ?
C11A N5A Cu1A 109.91(12) . . ?
C14A N5A Cu1A 117.57(13) . . ?
C10A N5A Cu1A 104.08(12) . . ?
N1A C1A C2A 120.3(2) . . ?
N1A C1A C10A 113.07(18) . . ?
C2A C1A C10A 126.43(19) . . ?
C3A C2A C1A 118.0(2) . . ?
C3A C2A H2A 121.0 . . ?
C1A C2A H2A 121.0 . . ?
C2A C3A C4A 120.9(2) . . ?
C2A C3A H3A 119.6 . . ?
C4A C3A H3A 119.6 . . ?
C5A C4A C3A 118.2(2) . . ?
C5A C4A H4A 120.9 . . ?
C3A C4A H4A 120.9 . . ?
N1A C5A C4A 119.70(19) . . ?
N1A C5A C6A 112.51(18) . . ?
C4A C5A C6A 127.74(19) . . ?
N2A C6A C5A 114.76(18) . . ?
N2A C6A H6A 122.6 . . ?
C5A C6A H6A 122.6 . . ?
N3A C7A N4A 117.11(18) . . ?
N3A C7A S1A 125.28(16) . . ?
N4A C7A S1A 117.62(16) . . ?
N4A C8A H8AA 109.5 . . ?
N4A C8A H8AB 109.5 . . ?
H8AA C8A H8AB 109.5 . . ?
N4A C8A H8AC 109.5 . . ?
H8AA C8A H8AC 109.5 . . ?
H8AB C8A H8AC 109.5 . . ?
N4A C9A H9AA 109.5 . . ?
N4A C9A H9AB 109.5 . . ?
H9AA C9A H9AB 109.5 . . ?
N4A C9A H9AC 109.5 . . ?
H9AA C9A H9AC 109.5 . . ?
H9AB C9A H9AC 109.5 . . ?
N5A C10A C1A 111.53(17) . . ?
N5A C10A H10A 109.3 . . ?
C1A C10A H10A 109.3 . . ?
N5A C10A H10B 109.3 . . ?
C1A C10A H10B 109.3 . . ?
H10A C10A H10B 108.0 . . ?
N5A C11A C12A 110.74(17) . . ?
N5A C11A H11A 109.5 . . ?
C12A C11A H11A 109.5 . . ?
N5A C11A H11B 109.5 . . ?
C12A C11A H11B 109.5 . . ?
H11A C11A H11B 108.1 . . ?
O1A C12A C11A 111.01(18) . . ?
O1A C12A H12A 109.4 . . ?
C11A C12A H12A 109.4 . . ?
O1A C12A H12B 109.4 . . ?
C11A C12A H12B 109.4 . . ?
H12A C12A H12B 108.0 . . ?
O1A C13A C14A 111.93(19) . . ?
O1A C13A H13A 109.2 . . ?
C14A C13A H13A 109.2 . . ?
O1A C13A H13B 109.2 . . ?
C14A C13A H13B 109.2 . . ?
H13A C13A H13B 107.9 . . ?
N5A C14A C13A 110.55(18) . . ?
N5A C14A H14A 109.5 . . ?
C13A C14A H14A 109.5 . . ?
N5A C14A H14B 109.5 . . ?
C13A C14A H14B 109.5 . . ?
H14A C14A H14B 108.1 . . ?
N1B Cu1B N2B 79.49(7) . . ?
N1B Cu1B N5B 78.61(7) . . ?
N2B Cu1B N5B 152.83(7) . . ?
N1B Cu1B S1B 156.86(5) . . ?
N2B Cu1B S1B 82.62(5) . . ?
N5B Cu1B S1B 113.35(5) . . ?
N1B Cu1B Cl1B 96.31(5) . . ?
N2B Cu1B Cl1B 104.61(5) . . ?
N5B Cu1B Cl1B 93.61(5) . . ?
S1B Cu1B Cl1B 102.34(2) . . ?
C7B S1B Cu1B 94.92(7) . . ?
C12B O1B C13B 110.23(17) . . ?
C1B N1B C5B 122.05(19) . . ?
C1B N1B Cu1B 121.33(15) . . ?
C5B N1B Cu1B 116.58(14) . . ?
C6B N2B N3B 120.24(18) . . ?
C6B N2B Cu1B 115.54(15) . . ?
N3B N2B Cu1B 124.13(14) . . ?
C7B N3B N2B 111.49(18) . . ?
C7B N4B C9B 123.3(2) . . ?
C7B N4B C8B 121.1(2) . . ?
C9B N4B C8B 115.42(19) . . ?
C14B N5B C10B 106.93(16) . . ?
C14B N5B C11B 108.15(17) . . ?
C10B N5B C11B 109.17(17) . . ?
C14B N5B Cu1B 117.65(13) . . ?
C10B N5B Cu1B 104.53(12) . . ?
C11B N5B Cu1B 110.09(13) . . ?
N1B C1B C2B 120.8(2) . . ?
N1B C1B C10B 112.95(18) . . ?
C2B C1B C10B 126.1(2) . . ?
C3B C2B C1B 117.9(2) . . ?
C3B C2B H2B 121.1 . . ?
C1B C2B H2B 121.1 . . ?
C2B C3B C4B 120.9(2) . . ?
C2B C3B H3B 119.5 . . ?
C4B C3B H3B 119.5 . . ?
C5B C4B C3B 118.2(2) . . ?
C5B C4B H4B 120.9 . . ?
C3B C4B H4B 120.9 . . ?
N1B C5B C4B 120.1(2) . . ?
N1B C5B C6B 112.72(19) . . ?
C4B C5B C6B 127.2(2) . . ?
N2B C6B C5B 115.45(19) . . ?
N2B C6B H6B 122.3 . . ?
C5B C6B H6B 122.3 . . ?
N3B C7B N4B 116.3(2) . . ?
N3B C7B S1B 124.44(16) . . ?
N4B C7B S1B 119.22(17) . . ?
N4B C8B H8BA 109.5 . . ?
N4B C8B H8BB 109.5 . . ?
H8BA C8B H8BB 109.5 . . ?
N4B C8B H8BC 109.5 . . ?
H8BA C8B H8BC 109.5 . . ?
H8BB C8B H8BC 109.5 . . ?
N4B C9B H9BA 109.5 . . ?
N4B C9B H9BB 109.5 . . ?
H9BA C9B H9BB 109.5 . . ?
N4B C9B H9BC 109.5 . . ?
H9BA C9B H9BC 109.5 . . ?
H9BB C9B H9BC 109.5 . . ?
N5B C10B C1B 111.24(17) . . ?
N5B C10B H10C 109.4 . . ?
C1B C10B H10C 109.4 . . ?
N5B C10B H10D 109.4 . . ?
C1B C10B H10D 109.4 . . ?
H10C C10B H10D 108.0 . . ?
N5B C11B C12B 110.61(18) . . ?
N5B C11B H11C 109.5 . . ?
C12B C11B H11C 109.5 . . ?
N5B C11B H11D 109.5 . . ?
C12B C11B H11D 109.5 . . ?
H11C C11B H11D 108.1 . . ?
O1B C12B C11B 112.11(19) . . ?
O1B C12B H12C 109.2 . . ?
C11B C12B H12C 109.2 . . ?
O1B C12B H12D 109.2 . . ?
C11B C12B H12D 109.2 . . ?
H12C C12B H12D 107.9 . . ?
O1B C13B C14B 111.51(19) . . ?
O1B C13B H13C 109.3 . . ?
C14B C13B H13C 109.3 . . ?
O1B C13B H13D 109.3 . . ?
C14B C13B H13D 109.3 . . ?
H13C C13B H13D 108.0 . . ?
N5B C14B C13B 110.75(18) . . ?
N5B C14B H14C 109.5 . . ?
C13B C14B H14C 109.5 . . ?
N5B C14B H14D 109.5 . . ?
C13B C14B H14D 109.5 . . ?
H14C C14B H14D 108.1 . . ?
C16B O3B H3BA 109.5 . . ?
O3B C16B H16D 109.5 . . ?
O3B C16B H16E 109.5 . . ?
H16D C16B H16E 109.5 . . ?
O3B C16B H16F 109.5 . . ?
H16D C16B H16F 109.5 . . ?
H16E C16B H16F 109.5 . . ?
C15 O2 H2 109.5 . . ?
O2 C15 H15A 109.5 . . ?
O2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1A Cu1A S1A C7A 44.50(17) . . . . ?
N2A Cu1A S1A C7A 9.02(8) . . . . ?
N5A Cu1A S1A C7A 167.50(8) . . . . ?
Cl1A Cu1A S1A C7A -93.11(7) . . . . ?
N2A Cu1A N1A C1A -176.31(17) . . . . ?
N5A Cu1A N1A C1A 20.01(15) . . . . ?
S1A Cu1A N1A C1A 147.78(13) . . . . ?
Cl1A Cu1A N1A C1A -73.17(15) . . . . ?
N2A Cu1A N1A C5A -6.78(15) . . . . ?
N5A Cu1A N1A C5A -170.46(16) . . . . ?
S1A Cu1A N1A C5A -42.7(3) . . . . ?
Cl1A Cu1A N1A C5A 96.36(14) . . . . ?
N1A Cu1A N2A C6A 4.69(15) . . . . ?
N5A Cu1A N2A C6A 43.7(2) . . . . ?
S1A Cu1A N2A C6A 172.95(15) . . . . ?
Cl1A Cu1A N2A C6A -84.42(15) . . . . ?
N1A Cu1A N2A N3A -178.18(16) . . . . ?
N5A Cu1A N2A N3A -139.21(16) . . . . ?
S1A Cu1A N2A N3A -9.92(14) . . . . ?
Cl1A Cu1A N2A N3A 92.71(15) . . . . ?
C6A N2A N3A C7A -177.94(18) . . . . ?
Cu1A N2A N3A C7A 5.1(2) . . . . ?
N1A Cu1A N5A C11A 87.89(13) . . . . ?
N2A Cu1A N5A C11A 48.9(2) . . . . ?
S1A Cu1A N5A C11A -75.03(13) . . . . ?
Cl1A Cu1A N5A C11A 178.80(12) . . . . ?
N1A Cu1A N5A C14A -147.53(15) . . . . ?
N2A Cu1A N5A C14A 173.53(15) . . . . ?
S1A Cu1A N5A C14A 49.55(15) . . . . ?
Cl1A Cu1A N5A C14A -56.62(14) . . . . ?
N1A Cu1A N5A C10A -28.85(13) . . . . ?
N2A Cu1A N5A C10A -67.8(2) . . . . ?
S1A Cu1A N5A C10A 168.23(11) . . . . ?
Cl1A Cu1A N5A C10A 62.06(12) . . . . ?
C5A N1A C1A C2A 1.6(3) . . . . ?
Cu1A N1A C1A C2A 170.43(15) . . . . ?
C5A N1A C1A C10A -173.47(18) . . . . ?
Cu1A N1A C1A C10A -4.6(2) . . . . ?
N1A C1A C2A C3A -1.7(3) . . . . ?
C10A C1A C2A C3A 172.7(2) . . . . ?
C1A C2A C3A C4A 1.1(3) . . . . ?
C2A C3A C4A C5A -0.4(3) . . . . ?
C1A N1A C5A C4A -0.8(3) . . . . ?
Cu1A N1A C5A C4A -169.97(16) . . . . ?
C1A N1A C5A C6A 176.74(18) . . . . ?
Cu1A N1A C5A C6A 7.6(2) . . . . ?
C3A C4A C5A N1A 0.2(3) . . . . ?
C3A C4A C5A C6A -177.0(2) . . . . ?
N3A N2A C6A C5A -179.16(17) . . . . ?
Cu1A N2A C6A C5A -2.0(2) . . . . ?
N1A C5A C6A N2A -3.5(3) . . . . ?
C4A C5A C6A N2A 173.8(2) . . . . ?
N2A N3A C7A N4A -174.37(17) . . . . ?
N2A N3A C7A S1A 5.9(2) . . . . ?
C9A N4A C7A N3A -178.68(19) . . . . ?
C8A N4A C7A N3A -5.2(3) . . . . ?
C9A N4A C7A S1A 1.0(3) . . . . ?
C8A N4A C7A S1A 174.51(16) . . . . ?
Cu1A S1A C7A N3A -11.43(18) . . . . ?
Cu1A S1A C7A N4A 168.87(15) . . . . ?
C11A N5A C10A C1A -82.6(2) . . . . ?
C14A N5A C10A C1A 160.04(17) . . . . ?
Cu1A N5A C10A C1A 34.65(19) . . . . ?
N1A C1A C10A N5A -22.5(2) . . . . ?
C2A C1A C10A N5A 162.8(2) . . . . ?
C14A N5A C11A C12A -55.4(2) . . . . ?
C10A N5A C11A C12A -172.16(17) . . . . ?
Cu1A N5A C11A C12A 74.30(18) . . . . ?
C13A O1A C12A C11A -59.4(2) . . . . ?
N5A C11A C12A O1A 58.7(2) . . . . ?
C12A O1A C13A C14A 59.2(2) . . . . ?
C11A N5A C14A C13A 54.7(2) . . . . ?
C10A N5A C14A C13A 172.46(17) . . . . ?
Cu1A N5A C14A C13A -70.7(2) . . . . ?
O1A C13A C14A N5A -57.7(2) . . . . ?
N1B Cu1B S1B C7B -51.05(16) . . . . ?
N2B Cu1B S1B C7B -11.51(9) . . . . ?
N5B Cu1B S1B C7B -168.61(9) . . . . ?
Cl1B Cu1B S1B C7B 91.91(7) . . . . ?
N2B Cu1B N1B C1B -178.37(17) . . . . ?
N5B Cu1B N1B C1B -14.54(16) . . . . ?
S1B Cu1B N1B C1B -138.42(14) . . . . ?
Cl1B Cu1B N1B C1B 77.88(16) . . . . ?
N2B Cu1B N1B C5B 3.69(15) . . . . ?
N5B Cu1B N1B C5B 167.52(16) . . . . ?
S1B Cu1B N1B C5B 43.6(2) . . . . ?
Cl1B Cu1B N1B C5B -100.06(15) . . . . ?
N1B Cu1B N2B C6B -4.25(15) . . . . ?
N5B Cu1B N2B C6B -41.0(2) . . . . ?
S1B Cu1B N2B C6B -169.51(16) . . . . ?
Cl1B Cu1B N2B C6B 89.60(15) . . . . ?
N1B Cu1B N2B N3B 179.20(17) . . . . ?
N5B Cu1B N2B N3B 142.48(16) . . . . ?
S1B Cu1B N2B N3B 13.95(15) . . . . ?
Cl1B Cu1B N2B N3B -86.95(16) . . . . ?
C6B N2B N3B C7B 174.84(19) . . . . ?
Cu1B N2B N3B C7B -8.8(2) . . . . ?
N1B Cu1B N5B C14B 144.90(16) . . . . ?
N2B Cu1B N5B C14B -178.25(15) . . . . ?
S1B Cu1B N5B C14B -55.92(16) . . . . ?
Cl1B Cu1B N5B C14B 49.18(15) . . . . ?
N1B Cu1B N5B C10B 26.51(13) . . . . ?
N2B Cu1B N5B C10B 63.4(2) . . . . ?
S1B Cu1B N5B C10B -174.30(11) . . . . ?
Cl1B Cu1B N5B C10B -69.20(12) . . . . ?
N1B Cu1B N5B C11B -90.62(14) . . . . ?
N2B Cu1B N5B C11B -53.8(2) . . . . ?
S1B Cu1B N5B C11B 68.57(14) . . . . ?
Cl1B Cu1B N5B C11B 173.67(13) . . . . ?
C5B N1B C1B C2B -0.8(3) . . . . ?
Cu1B N1B C1B C2B -178.68(16) . . . . ?
C5B N1B C1B C10B 175.51(19) . . . . ?
Cu1B N1B C1B C10B -2.3(2) . . . . ?
N1B C1B C2B C3B 1.2(3) . . . . ?
C10B C1B C2B C3B -174.7(2) . . . . ?
C1B C2B C3B C4B -0.5(3) . . . . ?
C2B C3B C4B C5B -0.4(3) . . . . ?
C1B N1B C5B C4B -0.2(3) . . . . ?
Cu1B N1B C5B C4B 177.75(16) . . . . ?
C1B N1B C5B C6B 179.42(19) . . . . ?
Cu1B N1B C5B C6B -2.7(2) . . . . ?
C3B C4B C5B N1B 0.8(3) . . . . ?
C3B C4B C5B C6B -178.7(2) . . . . ?
N3B N2B C6B C5B -179.25(18) . . . . ?
Cu1B N2B C6B C5B 4.1(2) . . . . ?
N1B C5B C6B N2B -1.0(3) . . . . ?
C4B C5B C6B N2B 178.6(2) . . . . ?
N2B N3B C7B N4B 175.32(18) . . . . ?
N2B N3B C7B S1B -5.4(3) . . . . ?
C9B N4B C7B N3B 173.4(2) . . . . ?
C8B N4B C7B N3B -2.5(3) . . . . ?
C9B N4B C7B S1B -5.9(3) . . . . ?
C8B N4B C7B S1B 178.21(17) . . . . ?
Cu1B S1B C7B N3B 13.31(19) . . . . ?
Cu1B S1B C7B N4B -167.42(16) . . . . ?
C14B N5B C10B C1B -160.73(18) . . . . ?
C11B N5B C10B C1B 82.5(2) . . . . ?
Cu1B N5B C10B C1B -35.28(19) . . . . ?
N1B C1B C10B N5B 27.2(3) . . . . ?
C2B C1B C10B N5B -156.6(2) . . . . ?
C14B N5B C11B C12B 55.2(2) . . . . ?
C10B N5B C11B C12B 171.25(17) . . . . ?
Cu1B N5B C11B C12B -74.55(19) . . . . ?
C13B O1B C12B C11B 57.8(2) . . . . ?
N5B C11B C12B O1B -57.3(2) . . . . ?
C12B O1B C13B C14B -58.2(2) . . . . ?
C10B N5B C14B C13B -173.58(18) . . . . ?
C11B N5B C14B C13B -56.1(2) . . . . ?
Cu1B N5B C14B C13B 69.3(2) . . . . ?
O1B C13B C14B N5B 58.7(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 Cl1B 0.84 2.36 3.193(2) 171.1 .
O3A H3AA Cl1A 0.84 2.33 3.109(6) 155.5 2_566

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.839
_refine_diff_density_min         -0.522
_refine_diff_density_rms         0.060
####################################################################### 
# 
# 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_feba272
_database_code_depnum_ccdc_archive 'CCDC 1052910'
_audit_update_record             
;
2015-03-09 deposited with the CCDC.
2015-04-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C12 H16 Cl Cu N5 O S), C4 H10 O'
_chemical_formula_sum            'C28 H42 Cl2 Cu2 N10 O3 S2'
_chemical_formula_weight         828.82

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n
_symmetry_space_group_name_Hall  '-P 2yn'

loop_
_symmetry_equiv_pos_as_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                   7.7969(6)
_cell_length_b                   17.4139(14)
_cell_length_c                   13.1450(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.700(2)
_cell_angle_gamma                90.00
_cell_volume                     1734.0(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9991
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      30.05

_exptl_crystal_description       block
_exptl_crystal_colour            grayish-blue
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.587
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             856
_exptl_absorpt_coefficient_mu    1.548
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8720
_exptl_absorpt_correction_T_max  0.9623
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            24073
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_sigmaI/netI    0.0341
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.98
_diffrn_reflns_theta_max         30.04
_reflns_number_total             4977
_reflns_number_gt                4177
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0266P)²+4.4941P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4977
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0424
_refine_ls_wR_factor_ref         0.0950
_refine_ls_wR_factor_gt          0.0902
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_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 0.46202(4) 0.315439(16) 0.53226(2) 0.01530(8) Uani 1 1 d . . .
Cl1 Cl 0.55488(7) 0.32231(3) 0.36473(4) 0.01838(12) Uani 1 1 d . . .
S1 S 0.16907(8) 0.29021(4) 0.47585(5) 0.02023(13) Uani 1 1 d . . .
C7 C 0.1009(3) 0.38506(14) 0.48288(19) 0.0170(4) Uani 1 1 d . . .
C1 C 0.8240(3) 0.31822(14) 0.64590(19) 0.0180(4) Uani 1 1 d . . .
N3 N 0.2070(3) 0.44295(12) 0.52633(18) 0.0209(4) Uani 1 1 d . . .
N1 N 0.6776(3) 0.35968(12) 0.61875(16) 0.0172(4) Uani 1 1 d . . .
N2 N 0.3769(3) 0.42009(12) 0.56040(17) 0.0185(4) Uani 1 1 d . . .
C2 C 0.9790(3) 0.35020(15) 0.7061(2) 0.0216(5) Uani 1 1 d . . .
H2 H 1.0832 0.3203 0.7277 0.026 Uiso 1 1 calc R . .
C5 C 0.6716(3) 0.43414(14) 0.6459(2) 0.0196(5) Uani 1 1 d . . .
C6 C 0.4960(3) 0.46733(14) 0.6106(2) 0.0217(5) Uani 1 1 d . . .
H6 H 0.4707 0.5193 0.6233 0.026 Uiso 1 1 calc R . .
C4 C 0.8223(3) 0.47007(15) 0.7033(2) 0.0238(5) Uani 1 1 d . . .
H4 H 0.8204 0.5228 0.7217 0.029 Uiso 1 1 calc R . .
C3 C 0.9763(3) 0.42712(16) 0.7334(2) 0.0244(5) Uani 1 1 d . . .
H3 H 1.0808 0.4507 0.7731 0.029 Uiso 1 1 calc R . .
N5 N 0.6151(3) 0.21278(11) 0.58457(16) 0.0165(4) Uani 1 1 d . . .
N4 N -0.0673(3) 0.40236(12) 0.44554(17) 0.0218(4) Uani 1 1 d . . .
H4A H -0.1042 0.4497 0.4500 0.026 Uiso 1 1 calc R . .
H4B H -0.1424 0.3665 0.4163 0.026 Uiso 1 1 calc R . .
C8 C 0.8024(3) 0.23864(14) 0.6011(2) 0.0191(5) Uani 1 1 d . . .
H8A H 0.8375 0.2380 0.5335 0.023 Uiso 1 1 calc R . .
H8B H 0.8804 0.2028 0.6495 0.023 Uiso 1 1 calc R . .
C9 C 0.5847(3) 0.18715(15) 0.6865(2) 0.0237(5) Uani 1 1 d . . .
H9A H 0.5870 0.2322 0.7328 0.028 Uiso 1 1 calc R . .
H9B H 0.6806 0.1519 0.7208 0.028 Uiso 1 1 calc R . .
C12 C 0.5908(3) 0.14646(14) 0.5115(2) 0.0202(5) Uani 1 1 d . . .
H12A H 0.6877 0.1092 0.5358 0.024 Uiso 1 1 calc R . .
H12B H 0.5970 0.1645 0.4410 0.024 Uiso 1 1 calc R . .
C11 C 0.4159(4) 0.10705(15) 0.5044(2) 0.0256(6) Uani 1 1 d . . .
H11A H 0.3188 0.1431 0.4747 0.031 Uiso 1 1 calc R . .
H11B H 0.4058 0.0624 0.4568 0.031 Uiso 1 1 calc R . .
C10 C 0.4092(4) 0.14665(17) 0.6720(2) 0.0279(6) Uani 1 1 d . . .
H10A H 0.3932 0.1295 0.7409 0.033 Uiso 1 1 calc R . .
H10B H 0.3128 0.1830 0.6419 0.033 Uiso 1 1 calc R . .
O1 O 0.3991(3) 0.08186(11) 0.60431(17) 0.0306(5) Uani 1 1 d . . .
O2 O 0.5199(8) 0.5497(4) 0.0149(5) 0.0578(15) Uiso 0.50 1 d P A -1
C15 C 0.4660(10) 0.4863(5) -0.0468(6) 0.0445(16) Uiso 0.50 1 d P A -1
H15A H 0.5428 0.4422 -0.0188 0.053 Uiso 0.50 1 calc PR A -1
H15B H 0.3437 0.4730 -0.0441 0.053 Uiso 0.50 1 calc PR A -1
C14 C 0.5288(10) 0.5465(5) 0.1182(6) 0.0458(17) Uiso 0.50 1 d P A -1
H14A H 0.6228 0.5101 0.1515 0.055 Uiso 0.50 1 calc PR A -1
H14B H 0.4154 0.5270 0.1293 0.055 Uiso 0.50 1 calc PR A -1
C13 C 0.5680(9) 0.6263(4) 0.1716(6) 0.0410(15) Uiso 0.50 1 d P A -1
H13A H 0.5947 0.6201 0.2478 0.062 Uiso 0.50 1 calc PR A -1
H13B H 0.4645 0.6596 0.1492 0.062 Uiso 0.50 1 calc PR A -1
H13C H 0.6694 0.6497 0.1514 0.062 Uiso 0.50 1 calc PR A -1
C16 C 0.4721(14) 0.4989(7) -0.1482(8) 0.075(3) Uiso 0.50 1 d P A -1
H16A H 0.5933 0.5116 -0.1513 0.113 Uiso 0.50 1 calc PR A -1
H16B H 0.3937 0.5417 -0.1768 0.113 Uiso 0.50 1 calc PR A -1
H16C H 0.4338 0.4526 -0.1896 0.113 Uiso 0.50 1 calc PR A -1


_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 1.951(2) . ?
Cu1 N2 2.004(2) . ?
Cu1 N5 2.169(2) . ?
Cu1 S1 2.2711(7) . ?
Cu1 Cl1 2.4786(7) . ?
S1 C7 1.744(2) . ?
C7 N4 1.322(3) . ?
C7 N3 1.343(3) . ?
C1 N1 1.326(3) . ?
C1 C2 1.394(3) . ?
C1 C8 1.500(3) . ?
N3 N2 1.353(3) . ?
N1 C5 1.349(3) . ?
N2 C6 1.298(3) . ?
C2 C3 1.388(4) . ?
C2 H2 0.9500 . ?
C5 C4 1.387(4) . ?
C5 C6 1.457(3) . ?
C6 H6 0.9500 . ?
C4 C3 1.390(4) . ?
C4 H4 0.9500 . ?
C3 H3 0.9500 . ?
N5 C9 1.484(3) . ?
N5 C12 1.486(3) . ?
N5 C8 1.494(3) . ?
N4 H4A 0.8800 . ?
N4 H4B 0.8800 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.510(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C12 C11 1.510(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C11 O1 1.420(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C10 O1 1.427(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
O2 C14 1.344(10) . ?
O2 C15 1.375(9) . ?
C15 C16 1.364(12) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C14 C13 1.554(10) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

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 79.09(8) . . ?
N1 Cu1 N5 78.88(8) . . ?
N2 Cu1 N5 150.76(8) . . ?
N1 Cu1 S1 158.09(6) . . ?
N2 Cu1 S1 83.37(6) . . ?
N5 Cu1 S1 112.30(6) . . ?
N1 Cu1 Cl1 96.08(6) . . ?
N2 Cu1 Cl1 107.42(6) . . ?
N5 Cu1 Cl1 93.83(6) . . ?
S1 Cu1 Cl1 101.66(2) . . ?
C7 S1 Cu1 95.44(8) . . ?
N4 C7 N3 116.4(2) . . ?
N4 C7 S1 118.95(19) . . ?
N3 C7 S1 124.67(18) . . ?
N1 C1 C2 120.7(2) . . ?
N1 C1 C8 112.8(2) . . ?
C2 C1 C8 126.4(2) . . ?
C7 N3 N2 112.1(2) . . ?
C1 N1 C5 122.3(2) . . ?
C1 N1 Cu1 120.64(17) . . ?
C5 N1 Cu1 117.03(16) . . ?
C6 N2 N3 120.5(2) . . ?
C6 N2 Cu1 116.22(17) . . ?
N3 N2 Cu1 123.19(16) . . ?
C3 C2 C1 117.9(2) . . ?
C3 C2 H2 121.0 . . ?
C1 C2 H2 121.0 . . ?
N1 C5 C4 120.0(2) . . ?
N1 C5 C6 112.7(2) . . ?
C4 C5 C6 127.3(2) . . ?
N2 C6 C5 114.6(2) . . ?
N2 C6 H6 122.7 . . ?
C5 C6 H6 122.7 . . ?
C5 C4 C3 118.4(2) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
C2 C3 C4 120.7(2) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C9 N5 C12 109.10(19) . . ?
C9 N5 C8 108.63(19) . . ?
C12 N5 C8 107.39(19) . . ?
C9 N5 Cu1 109.89(15) . . ?
C12 N5 Cu1 117.35(15) . . ?
C8 N5 Cu1 104.07(14) . . ?
C7 N4 H4A 120.0 . . ?
C7 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
N5 C8 C1 110.52(19) . . ?
N5 C8 H8A 109.5 . . ?
C1 C8 H8A 109.5 . . ?
N5 C8 H8B 109.5 . . ?
C1 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
N5 C9 C10 111.1(2) . . ?
N5 C9 H9A 109.4 . . ?
C10 C9 H9A 109.4 . . ?
N5 C9 H9B 109.4 . . ?
C10 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
N5 C12 C11 111.6(2) . . ?
N5 C12 H12A 109.3 . . ?
C11 C12 H12A 109.3 . . ?
N5 C12 H12B 109.3 . . ?
C11 C12 H12B 109.3 . . ?
H12A C12 H12B 108.0 . . ?
O1 C11 C12 111.3(2) . . ?
O1 C11 H11A 109.4 . . ?
C12 C11 H11A 109.4 . . ?
O1 C11 H11B 109.4 . . ?
C12 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
O1 C10 C9 111.3(2) . . ?
O1 C10 H10A 109.4 . . ?
C9 C10 H10A 109.4 . . ?
O1 C10 H10B 109.4 . . ?
C9 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
C11 O1 C10 109.2(2) . . ?
C14 O2 C15 119.9(7) . . ?
C16 C15 O2 111.8(9) . . ?
C16 C15 H15A 109.3 . . ?
O2 C15 H15A 109.3 . . ?
C16 C15 H15B 109.3 . . ?
O2 C15 H15B 109.3 . . ?
H15A C15 H15B 107.9 . . ?
O2 C14 C13 112.1(7) . . ?
O2 C14 H14A 109.2 . . ?
C13 C14 H14A 109.2 . . ?
O2 C14 H14B 109.2 . . ?
C13 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 Cu1 S1 C7 45.23(19) . . . . ?
N2 Cu1 S1 C7 8.30(10) . . . . ?
N5 Cu1 S1 C7 162.70(10) . . . . ?
Cl1 Cu1 S1 C7 -98.19(8) . . . . ?
Cu1 S1 C7 N4 172.71(19) . . . . ?
Cu1 S1 C7 N3 -9.0(2) . . . . ?
N4 C7 N3 N2 -178.8(2) . . . . ?
S1 C7 N3 N2 2.8(3) . . . . ?
C2 C1 N1 C5 1.1(4) . . . . ?
C8 C1 N1 C5 -176.2(2) . . . . ?
C2 C1 N1 Cu1 178.81(18) . . . . ?
C8 C1 N1 Cu1 1.5(3) . . . . ?
N2 Cu1 N1 C1 177.1(2) . . . . ?
N5 Cu1 N1 C1 16.41(18) . . . . ?
S1 Cu1 N1 C1 139.63(17) . . . . ?
Cl1 Cu1 N1 C1 -76.31(19) . . . . ?
N2 Cu1 N1 C5 -5.15(18) . . . . ?
N5 Cu1 N1 C5 -165.80(19) . . . . ?
S1 Cu1 N1 C5 -42.6(3) . . . . ?
Cl1 Cu1 N1 C5 101.47(18) . . . . ?
C7 N3 N2 C6 -175.6(2) . . . . ?
C7 N3 N2 Cu1 7.2(3) . . . . ?
N1 Cu1 N2 C6 5.41(19) . . . . ?
N5 Cu1 N2 C6 47.1(3) . . . . ?
S1 Cu1 N2 C6 172.21(19) . . . . ?
Cl1 Cu1 N2 C6 -87.61(19) . . . . ?
N1 Cu1 N2 N3 -177.2(2) . . . . ?
N5 Cu1 N2 N3 -135.50(19) . . . . ?
S1 Cu1 N2 N3 -10.42(18) . . . . ?
Cl1 Cu1 N2 N3 89.76(19) . . . . ?
N1 C1 C2 C3 -2.1(4) . . . . ?
C8 C1 C2 C3 174.8(2) . . . . ?
C1 N1 C5 C4 0.6(4) . . . . ?
Cu1 N1 C5 C4 -177.13(19) . . . . ?
C1 N1 C5 C6 -178.1(2) . . . . ?
Cu1 N1 C5 C6 4.2(3) . . . . ?
N3 N2 C6 C5 177.9(2) . . . . ?
Cu1 N2 C6 C5 -4.7(3) . . . . ?
N1 C5 C6 N2 0.4(3) . . . . ?
C4 C5 C6 N2 -178.1(3) . . . . ?
N1 C5 C4 C3 -1.3(4) . . . . ?
C6 C5 C4 C3 177.1(3) . . . . ?
C1 C2 C3 C4 1.3(4) . . . . ?
C5 C4 C3 C2 0.3(4) . . . . ?
N1 Cu1 N5 C9 87.41(16) . . . . ?
N2 Cu1 N5 C9 45.6(2) . . . . ?
S1 Cu1 N5 C9 -72.87(16) . . . . ?
Cl1 Cu1 N5 C9 -177.14(15) . . . . ?
N1 Cu1 N5 C12 -147.23(18) . . . . ?
N2 Cu1 N5 C12 171.02(17) . . . . ?
S1 Cu1 N5 C12 52.49(17) . . . . ?
Cl1 Cu1 N5 C12 -51.77(16) . . . . ?
N1 Cu1 N5 C8 -28.76(15) . . . . ?
N2 Cu1 N5 C8 -70.5(2) . . . . ?
S1 Cu1 N5 C8 170.96(13) . . . . ?
Cl1 Cu1 N5 C8 66.70(14) . . . . ?
C9 N5 C8 C1 -79.5(2) . . . . ?
C12 N5 C8 C1 162.6(2) . . . . ?
Cu1 N5 C8 C1 37.6(2) . . . . ?
N1 C1 C8 N5 -28.3(3) . . . . ?
C2 C1 C8 N5 154.6(2) . . . . ?
C12 N5 C9 C10 -52.6(3) . . . . ?
C8 N5 C9 C10 -169.4(2) . . . . ?
Cu1 N5 C9 C10 77.4(2) . . . . ?
C9 N5 C12 C11 52.3(3) . . . . ?
C8 N5 C12 C11 169.9(2) . . . . ?
Cu1 N5 C12 C11 -73.4(2) . . . . ?
N5 C12 C11 O1 -57.4(3) . . . . ?
N5 C9 C10 O1 58.2(3) . . . . ?
C12 C11 O1 C10 60.5(3) . . . . ?
C9 C10 O1 C11 -61.1(3) . . . . ?
C14 O2 C15 C16 -177.4(8) . . . . ?
C15 O2 C14 C13 -172.4(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C11 H11A S1 0.99 2.82 3.698(3) 148.6 .
N4 H4A N3 0.88 2.09 2.962(3) 173.1 3_566
N4 H4B Cl1 0.88 2.42 3.204(2) 148.4 1_455

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.541
_refine_diff_density_min         -0.640
_refine_diff_density_rms         0.094
