# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1563399'
_audit_update_record             
;
2018-04-17 deposited with the CCDC.
2018-04-25 downloaded from the CCDC.
;

_audit_creation_date             2018-04-17T15:44:41-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C18 H23 N3 O3'
_chemical_formula_weight         329.39

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_Int_Tables_number      15
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   21.0616(14)
_cell_length_b                   6.5769(6)
_cell_length_c                   25.0650(18)
_cell_angle_alpha                90
_cell_angle_beta                 104.603(7)
_cell_angle_gamma                90
_cell_volume                     3359.8(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    1437
_cell_measurement_theta_min      3.93
_cell_measurement_theta_max      28.48
_cell_measurement_wavelength     0

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1408

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.09
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
        (compiled Jan 14 2014,18:38:05)
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.99
_exptl_absorpt_correction_T_max  1

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_ambient_temperature      190(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.07
_diffrn_orient_matrix_ub_11      -0.010073
_diffrn_orient_matrix_ub_12      -0.004925
_diffrn_orient_matrix_ub_13      -0.029208
_diffrn_orient_matrix_ub_21      -0.004174
_diffrn_orient_matrix_ub_22      0.107087
_diffrn_orient_matrix_ub_23      -0.001248
_diffrn_orient_matrix_ub_31      0.033045
_diffrn_orient_matrix_ub_32      0.011831
_diffrn_orient_matrix_ub_33      -0.001257
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  
'Agilent Technologies Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_number            4726
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.255
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_reflns_Friedel_coverage         0
_reflns_number_total             2937
_reflns_number_gt                2232
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
 Scaled and merged with Sortav
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
'CrysalisPro  Version 1.171.37.31 (Agilent Technologies, 2014)'
_computing_cell_refinement       
'CrysalisPro  Version 1.171.37.31 (Agilent Technologies, 2014)'
_computing_data_reduction        
'CrysalisPro  Version 1.171.37.31 (Agilent Technologies, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0325P)²+1.7117P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2937
_refine_ls_number_parameters     256
_refine_ls_number_restraints     24
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0444
_refine_ls_wR_factor_ref         0.1047
_refine_ls_wR_factor_gt          0.0966
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.037

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.09013(8) -0.4921(3) -0.05209(7) 0.0295(4) Uani 1 1 d . . . . .
C2 C 0.06179(8) -0.6774(3) -0.07127(8) 0.0340(5) Uani 1 1 d . . . . .
C3 C 0.07976(9) -0.7751(3) -0.11399(8) 0.0375(5) Uani 1 1 d . . . . .
H3 H 0.060145 -0.901323 -0.127354 0.045 Uiso 1 1 calc R U . . .
C4 C 0.12641(9) -0.6890(3) -0.13737(8) 0.0418(5) Uani 1 1 d . . . . .
H4 H 0.138635 -0.756125 -0.166832 0.05 Uiso 1 1 calc R U . . .
C5 C 0.15515(9) -0.5060(3) -0.11799(8) 0.0384(5) Uani 1 1 d . . . . .
H5 H 0.18708 -0.448366 -0.134324 0.046 Uiso 1 1 calc R U . . .
C6 C 0.13803(8) -0.4039(3) -0.07466(7) 0.0288(4) Uani 1 1 d . . . . .
C7 C 0.17038(8) -0.2149(3) -0.05402(7) 0.0330(5) Uani 1 1 d . . . . .
H7 H 0.200921 -0.157878 -0.071961 0.04 Uiso 1 1 calc R U . . .
C8 C 0.18712(8) 0.1690(3) 0.04775(7) 0.0317(4) Uani 1 1 d . . . . .
C9 C 0.13587(9) 0.1791(3) 0.12845(7) 0.0314(4) Uani 1 1 d . . . . .
C10 C 0.09346(12) 0.0225(4) 0.14872(9) 0.0477(7) Uani 0.901(3) 1 d D . P A 1
H10A H 0.117471 -0.10792 0.156582 0.057 Uiso 0.901(3) 1 calc R U P A 1
H10B H 0.052565 -0.001815 0.119721 0.057 Uiso 0.901(3) 1 calc R U P A 1
C11 C 0.07656(14) 0.1015(5) 0.20149(17) 0.0505(9) Uani 0.901(3) 1 d D . P A 1
H11 H 0.047604 0.001437 0.214006 0.061 Uiso 0.901(3) 1 calc R U P A 1
C12 C 0.04148(12) 0.3036(6) 0.18903(14) 0.0568(9) Uani 0.901(3) 1 d D . P A 1
H12A H 0.03016 0.35514 0.222576 0.068 Uiso 0.901(3) 1 calc R U P A 1
H12B H 0.00021 0.284882 0.160043 0.068 Uiso 0.901(3) 1 calc R U P A 1
C13 C 0.14840(15) 0.4843(4) 0.21444(18) 0.0449(9) Uani 0.901(3) 1 d D . P A 1
H13A H 0.177087 0.583234 0.202004 0.054 Uiso 0.901(3) 1 calc R U P A 1
H13B H 0.138465 0.538414 0.248299 0.054 Uiso 0.901(3) 1 calc R U P A 1
C14 C 0.18351(12) 0.2823(4) 0.22689(13) 0.0425(8) Uani 0.901(3) 1 d D . P A 1
H14 H 0.224993 0.301331 0.2564 0.051 Uiso 0.901(3) 1 calc R U P A 1
C15 C 0.20004(10) 0.2045(4) 0.17401(8) 0.0374(6) Uani 0.901(3) 1 d D . P A 1
H15A H 0.223124 0.072336 0.181315 0.045 Uiso 0.901(3) 1 calc R U P A 1
H15B H 0.229255 0.302447 0.161914 0.045 Uiso 0.901(3) 1 calc R U P A 1
C16 C 0.10094(10) 0.3790(4) 0.11708(9) 0.0389(6) Uani 0.901(3) 1 d D . P A 1
H16A H 0.059929 0.362097 0.087691 0.047 Uiso 0.901(3) 1 calc R U P A 1
H16B H 0.129024 0.478616 0.10419 0.047 Uiso 0.901(3) 1 calc R U P A 1
C17 C 0.08485(11) 0.4576(4) 0.16967(10) 0.0447(6) Uani 0.901(3) 1 d D . P A 1
H17 H 0.06147 0.590902 0.162088 0.054 Uiso 0.901(3) 1 calc R U P A 1
C18 C 0.13990(13) 0.1285(4) 0.24610(10) 0.0541(7) Uani 0.901(3) 1 d D . P A 1
H18A H 0.162991 -0.003446 0.253853 0.065 Uiso 0.901(3) 1 calc R U P A 1
H18B H 0.129915 0.176991 0.280489 0.065 Uiso 0.901(3) 1 calc R U P A 1
C10' C 0.0556(6) 0.195(2) 0.1205(5) 0.037(5) Uiso 0.099(3) 1 d D . P A 2
H10C H 0.037219 0.305479 0.094257 0.044 Uiso 0.099(3) 1 calc R U P A 2
H10D H 0.034268 0.065806 0.105599 0.044 Uiso 0.099(3) 1 calc R U P A 2
C11' C 0.0425(6) 0.240(3) 0.1773(6) 0.041(9) Uiso 0.099(3) 1 d D . P A 2
H11' H -0.005708 0.234314 0.174378 0.049 Uiso 0.099(3) 1 calc R U P A 2
C12' C 0.0685(8) 0.450(2) 0.1958(7) 0.045(6) Uiso 0.099(3) 1 d D . P A 2
H12C H 0.060249 0.480462 0.232105 0.054 Uiso 0.099(3) 1 calc R U P A 2
H12D H 0.045226 0.552206 0.169044 0.054 Uiso 0.099(3) 1 calc R U P A 2
C13' C 0.1771(8) 0.301(3) 0.2411(6) 0.09(2) Uiso 0.099(3) 1 d D . P A 2
H13C H 0.224814 0.306746 0.243843 0.11 Uiso 0.099(3) 1 calc R U P A 2
H13D H 0.170339 0.330499 0.278023 0.11 Uiso 0.099(3) 1 calc R U P A 2
C14' C 0.1511(8) 0.092(2) 0.2226(6) 0.070(9) Uiso 0.099(3) 1 d D . P A 2
H14' H 0.174416 -0.011752 0.249886 0.084 Uiso 0.099(3) 1 calc R U P A 2
C15' C 0.1642(6) 0.048(2) 0.1659(6) 0.031(5) Uiso 0.099(3) 1 d D . P A 2
H15C H 0.212148 0.050898 0.169589 0.038 Uiso 0.099(3) 1 calc R U P A 2
H15D H 0.148207 -0.089971 0.153798 0.038 Uiso 0.099(3) 1 calc R U P A 2
C16' C 0.1545(7) 0.418(2) 0.1437(7) 0.044(6) Uiso 0.099(3) 1 d D . P A 2
H16C H 0.201207 0.442731 0.144827 0.053 Uiso 0.099(3) 1 calc R U P A 2
H16D H 0.12715 0.507762 0.115357 0.053 Uiso 0.099(3) 1 calc R U P A 2
C17' C 0.1419(8) 0.461(2) 0.2001(7) 0.057(16) Uiso 0.099(3) 1 d D . P A 2
H17' H 0.158621 0.5998 0.212983 0.069 Uiso 0.099(3) 1 calc R U P A 2
C18' C 0.0777(8) 0.081(3) 0.2180(7) 0.072(17) Uiso 0.099(3) 1 d D . P A 2
H18C H 0.06109 -0.056502 0.205281 0.087 Uiso 0.099(3) 1 calc R U P A 2
H18D H 0.06926 0.104797 0.254563 0.087 Uiso 0.099(3) 1 calc R U P A 2
N1 N 0.15912(7) -0.1214(2) -0.01212(6) 0.0313(4) Uani 1 1 d . . . . .
N2 N 0.19265(7) 0.0569(3) 0.00310(6) 0.0363(4) Uani 1 1 d . . . . .
H2 H 0.218868 0.101124 -0.01671 0.044 Uiso 1 1 calc R U . . .
N3 N 0.14842(8) 0.0906(3) 0.07789(7) 0.0465(5) Uani 1 1 d . . . . .
H3A H 0.128599 -0.024884 0.066321 0.056 Uiso 1 1 calc R U . . .
O1 O 0.06919(6) -0.4014(2) -0.01033(5) 0.0412(4) Uani 1 1 d . . . . .
H1 H 0.091762 -0.296916 0.000319 0.062 Uiso 1 1 calc R U . . .
O2 O 0.01692(7) -0.7679(2) -0.04779(6) 0.0510(4) Uani 1 1 d . . . . .
H2A H 0.007847 -0.688838 -0.024445 0.077 Uiso 1 1 calc R U . . .
O3 O 0.21808(6) 0.3292(2) 0.05858(5) 0.0382(4) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1 O1 1.371(2) . ?
C1 C2 1.389(3) . ?
C1 C6 1.401(2) . ?
C2 O2 1.369(2) . ?
C2 C3 1.381(3) . ?
C3 C4 1.386(3) . ?
C4 C5 1.379(3) . ?
C5 C6 1.399(2) . ?
C6 C7 1.449(3) . ?
C7 N1 1.290(2) . ?
C8 O3 1.232(2) . ?
C8 N3 1.346(2) . ?
C8 N2 1.370(2) . ?
C9 C15' 1.303(13) . ?
C9 N3 1.478(2) . ?
C9 C16 1.498(3) . ?
C9 C10 1.531(3) . ?
C9 C15 1.543(3) . ?
C9 C16' 1.639(14) . ?
C9 C10' 1.656(12) . ?
C10 C11 1.544(4) . ?
C11 C12 1.514(4) . ?
C11 C18 1.520(4) . ?
C12 C17 1.523(4) . ?
C13 C14 1.514(4) . ?
C13 C17 1.525(4) . ?
C14 C18 1.524(4) . ?
C14 C15 1.540(4) . ?
C16 C17 1.531(3) . ?
C10' C11' 1.545(6) . ?
C11' C12' 1.513(7) . ?
C11' C18' 1.520(6) . ?
C12' C17' 1.523(6) . ?
C13' C14' 1.514(6) . ?
C13' C17' 1.526(7) . ?
C14' C18' 1.522(6) . ?
C14' C15' 1.541(6) . ?
C16' C17' 1.532(6) . ?
N1 N2 1.372(2) . ?

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
O1 C1 C2 116.96(16) . . ?
O1 C1 C6 122.10(17) . . ?
C2 C1 C6 120.93(17) . . ?
O2 C2 C3 119.01(18) . . ?
O2 C2 C1 121.05(17) . . ?
C3 C2 C1 119.93(17) . . ?
C2 C3 C4 120.00(19) . . ?
C5 C4 C3 120.18(19) . . ?
C4 C5 C6 121.07(18) . . ?
C5 C6 C1 117.87(18) . . ?
C5 C6 C7 119.93(16) . . ?
C1 C6 C7 122.19(16) . . ?
N1 C7 C6 122.24(16) . . ?
O3 C8 N3 124.43(18) . . ?
O3 C8 N2 119.41(16) . . ?
N3 C8 N2 116.14(17) . . ?
C15' C9 N3 102.1(6) . . ?
N3 C9 C16 111.58(17) . . ?
N3 C9 C10 105.37(16) . . ?
C16 C9 C10 110.71(17) . . ?
N3 C9 C15 111.39(15) . . ?
C16 C9 C15 110.03(17) . . ?
C10 C9 C15 107.61(17) . . ?
C15' C9 C16' 115.2(8) . . ?
N3 C9 C16' 119.5(5) . . ?
C15' C9 C10' 113.4(8) . . ?
N3 C9 C10' 108.7(5) . . ?
C16' C9 C10' 98.3(7) . . ?
C9 C10 C11 109.73(19) . . ?
C12 C11 C18 110.0(3) . . ?
C12 C11 C10 108.9(3) . . ?
C18 C11 C10 108.7(2) . . ?
C11 C12 C17 110.4(2) . . ?
C14 C13 C17 110.1(3) . . ?
C13 C14 C18 110.2(2) . . ?
C13 C14 C15 108.6(3) . . ?
C18 C14 C15 109.6(2) . . ?
C14 C15 C9 109.09(16) . . ?
C9 C16 C17 109.70(18) . . ?
C12 C17 C13 109.1(2) . . ?
C12 C17 C16 109.3(2) . . ?
C13 C17 C16 109.2(2) . . ?
C11 C18 C14 109.4(2) . . ?
C11' C10' C9 108.4(7) . . ?
C12' C11' C18' 110.2(7) . . ?
C12' C11' C10' 108.7(7) . . ?
C18' C11' C10' 108.5(7) . . ?
C11' C12' C17' 110.5(6) . . ?
C14' C13' C17' 110.2(6) . . ?
C13' C14' C18' 110.4(7) . . ?
C13' C14' C15' 108.4(7) . . ?
C18' C14' C15' 109.6(7) . . ?
C9 C15' C14' 112.7(7) . . ?
C17' C16' C9 107.9(7) . . ?
C12' C17' C13' 109.0(7) . . ?
C12' C17' C16' 109.5(7) . . ?
C13' C17' C16' 108.9(7) . . ?
C11' C18' C14' 109.5(6) . . ?
C7 N1 N2 116.51(15) . . ?
C8 N2 N1 122.92(15) . . ?
C8 N3 C9 126.52(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
_geom_hbond_publ_flag
N2 H2 O3 0.88 1.94 2.8201(19) 173.7 7 yes
N3 H3A N1 0.88 2.31 2.709(2) 107.9 . yes
O1 H1 N1 0.84 1.91 2.6503(19) 145.6 . yes
O2 H2A O1 0.84 2.11 2.8254(18) 142.7 5_545 yes
O2 H2A O1 0.84 2.27 2.717(2) 113.8 . yes



# END of CIF
####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1563400'
_audit_update_record             
;
2018-04-17 deposited with the CCDC.
2018-04-25 downloaded from the CCDC.
;

_audit_creation_date             2018-04-17T14:53:47-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C19 H26 Cl2 Cu1 N4 O3, 0.75 C H4 O'
_chemical_formula_sum            'C19.75 H29 Cl2 Cu N4 O3.75'
_chemical_formula_weight         516.91
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.6653(5)
_cell_length_b                   12.8542(6)
_cell_length_c                   22.1094(10)
_cell_angle_alpha                99.037(5)
_cell_angle_beta                 93.119(5)
_cell_angle_gamma                105.051(5)
_cell_volume                     2336.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    5065
_cell_measurement_theta_min      3.58
_cell_measurement_theta_max      62.38
_cell_measurement_wavelength     1.5418

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.03
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1074
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 0 0.143
0 1 0 0.173
-1 0 0 0.064
1 0 0 0.078
0 0 -1 0.007
0 0 1 0.008


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    3.693
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
        model based on expressions derived by R.C. Clark & J.S.
        (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.432
_exptl_absorpt_correction_T_max  0.947

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_ambient_temperature      190(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.07
_diffrn_orient_matrix_ub_11      0.030223
_diffrn_orient_matrix_ub_12      0.002736
_diffrn_orient_matrix_ub_13      -0.067829
_diffrn_orient_matrix_ub_21      0.119366
_diffrn_orient_matrix_ub_22      0.114227
_diffrn_orient_matrix_ub_23      0.019154
_diffrn_orient_matrix_ub_31      0.138105
_diffrn_orient_matrix_ub_32      -0.053371
_diffrn_orient_matrix_ub_33      0.007772
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  
'Agilent Technologies Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0497
_diffrn_reflns_av_unetI/netI     0.0536
_diffrn_reflns_number            17869
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.618
_diffrn_reflns_theta_max         62.482
_diffrn_reflns_theta_full        62.482
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_reflns_Friedel_coverage         0
_reflns_number_total             7361
_reflns_number_gt                6296
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysalisPro (Agilent Technologies,     )'
_computing_cell_refinement       'CrysalisPro (Agilent Technologies,     )'
_computing_data_reduction        'CrysalisPro (Agilent Technologies,     )'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1124P)²+16.2996P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         7361
_refine_ls_number_parameters     576
_refine_ls_number_restraints     1
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.1086
_refine_ls_R_factor_gt           0.0996
_refine_ls_wR_factor_ref         0.2604
_refine_ls_wR_factor_gt          0.2531
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         2.01
_refine_diff_density_min         -1.337
_refine_diff_density_rms         0.122

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1A C 0.2555(9) 0.4404(6) 0.4570(4) 0.0392(16) Uani 1 1 d . . . . .
C2A C 0.1919(9) 0.5282(6) 0.4451(4) 0.0410(17) Uani 1 1 d . . . . .
C3A C 0.1793(9) 0.6086(6) 0.4945(4) 0.0426(17) Uani 1 1 d . . . . .
C4A C 0.2310(10) 0.6030(7) 0.5528(4) 0.0466(19) Uani 1 1 d . . . . .
H4A H 0.221257 0.656351 0.586255 0.056 Uiso 1 1 calc R U . . .
C5A C 0.3114(9) 0.4428(6) 0.5187(4) 0.0436(18) Uani 1 1 d . . . . .
C6A C 0.1111(11) 0.7023(7) 0.4841(4) 0.051(2) Uani 1 1 d . . . . .
H6A H 0.007798 0.67278 0.457795 0.062 Uiso 1 1 calc R U . . .
H6B H 0.08942 0.739624 0.524098 0.062 Uiso 1 1 calc R U . . .
C7A C 0.3828(10) 0.3563(7) 0.5362(4) 0.0486(19) Uani 1 1 d . . . . .
H7A H 0.442702 0.382355 0.577 0.073 Uiso 1 1 calc R U . . .
H7B H 0.455595 0.339877 0.505928 0.073 Uiso 1 1 calc R U . . .
H7C H 0.29682 0.289846 0.537013 0.073 Uiso 1 1 calc R U . . .
C8A C 0.1440(9) 0.5392(6) 0.3831(3) 0.0384(16) Uani 1 1 d . . . . .
H8A H 0.114708 0.603358 0.377156 0.046 Uiso 1 1 calc R U . . .
C9A C 0.1196(10) 0.4104(6) 0.2302(4) 0.0442(18) Uani 1 1 d . . . . .
C10A C 0.1223(11) 0.3700(7) 0.1158(4) 0.049(2) Uani 1 1 d . . . . .
C11A C 0.2785(13) 0.3352(9) 0.1166(4) 0.066(3) Uani 1 1 d . . . . .
H11A H 0.281351 0.289526 0.148605 0.079 Uiso 1 1 calc R U . . .
H11B H 0.371999 0.400568 0.126311 0.079 Uiso 1 1 calc R U . . .
C12A C 0.2855(16) 0.2691(10) 0.0525(5) 0.078(3) Uani 1 1 d . . . . .
H12A H 0.386088 0.244773 0.053231 0.093 Uiso 1 1 calc R U . . .
C13A C 0.2912(17) 0.3438(11) 0.0039(5) 0.084(4) Uani 1 1 d . . . . .
H13A H 0.384207 0.409342 0.014838 0.101 Uiso 1 1 calc R U . . .
H13B H 0.301989 0.303972 -0.037094 0.101 Uiso 1 1 calc R U . . .
C14A C 0.1336(16) 0.3779(9) 0.0026(4) 0.074(3) Uani 1 1 d . . . . .
H14A H 0.132643 0.425287 -0.029183 0.088 Uiso 1 1 calc R U . . .
C15A C 0.1248(14) 0.4431(8) 0.0669(4) 0.063(3) Uani 1 1 d . . . . .
H15A H 0.218908 0.508036 0.077005 0.076 Uiso 1 1 calc R U . . .
H15B H 0.026529 0.468769 0.066546 0.076 Uiso 1 1 calc R U . . .
C16A C -0.0182(13) 0.2714(8) 0.1000(4) 0.065(2) Uani 1 1 d . . . . .
H16A H -0.119031 0.293992 0.099448 0.078 Uiso 1 1 calc R U . . .
H16B H -0.020112 0.224362 0.131597 0.078 Uiso 1 1 calc R U . . .
C17A C -0.0061(17) 0.2064(10) 0.0362(5) 0.085(3) Uani 1 1 d . . . . .
H17A H -0.100526 0.140381 0.026248 0.102 Uiso 1 1 calc R U . . .
C18A C 0.1446(19) 0.1699(10) 0.0377(5) 0.090(4) Uani 1 1 d . . . . .
H18A H 0.143995 0.123249 0.069364 0.108 Uiso 1 1 calc R U . . .
H18B H 0.151562 0.126597 -0.002717 0.108 Uiso 1 1 calc R U . . .
C19A C -0.0106(17) 0.2786(12) -0.0118(5) 0.090(4) Uani 1 1 d . . . . .
H19A H -0.008403 0.237076 -0.053324 0.108 Uiso 1 1 calc R U . . .
H19B H -0.110748 0.302012 -0.011335 0.108 Uiso 1 1 calc R U . . .
N1A N 0.2960(8) 0.5222(5) 0.5633(3) 0.0478(16) Uani 1 1 d . . . . .
H1M H 0.330207 0.521418 0.601406 0.057 Uiso 1 1 calc R U . . .
N2A N 0.1395(7) 0.4657(5) 0.3360(3) 0.0389(14) Uani 1 1 d . . . . .
N3A N 0.0987(9) 0.4849(5) 0.2788(3) 0.0453(16) Uani 1 1 d . . . . .
H3A H 0.061896 0.540899 0.273493 0.054 Uiso 1 1 calc R U . . .
N4A N 0.1085(9) 0.4357(5) 0.1749(3) 0.0496(17) Uani 1 1 d . . . . .
H4M H 0.090688 0.499584 0.173245 0.06 Uiso 1 1 calc R U . . .
O1A O 0.2178(9) 0.7795(5) 0.4555(3) 0.0645(17) Uani 1 1 d . . . . .
H1A H 0.306089 0.76405 0.453805 0.097 Uiso 1 1 calc R U . . .
O2A O 0.2727(7) 0.3615(4) 0.4166(2) 0.0470(13) Uani 1 1 d . . . . .
O3A O 0.1492(8) 0.3242(4) 0.2417(2) 0.0528(15) Uani 1 1 d . . . . .
Cl1A Cl 0.3198(3) 0.19207(16) 0.31093(10) 0.0520(5) Uani 1 1 d . . . . .
Cl2A Cl -0.0841(3) 0.20634(16) 0.34733(10) 0.0539(5) Uani 1 1 d . . . . .
Cu1 Cu 0.19003(15) 0.32320(9) 0.33078(5) 0.0435(3) Uani 1 1 d . . . . .
C1B C 0.3344(9) 0.7759(6) 0.3051(4) 0.0436(18) Uani 1 1 d . . . . .
C2B C 0.3561(10) 0.8821(6) 0.3406(4) 0.0457(19) Uani 1 1 d . . . . .
C3B C 0.5018(11) 0.9373(7) 0.3749(4) 0.050(2) Uani 1 1 d . . . . .
C4B C 0.6250(12) 0.8871(8) 0.3742(4) 0.056(2) Uani 1 1 d . . . . .
H4B H 0.724781 0.922655 0.397928 0.068 Uiso 1 1 calc R U . . .
C5B C 0.4671(10) 0.7320(7) 0.3055(4) 0.0478(19) Uani 1 1 d . . . . .
C6B C 0.546(3) 1.062(3) 0.4078(15) 0.033(6) Uani 0.546(19) 1 d . . P A 1
H6C H 0.664502 1.091738 0.41487 0.04 Uiso 0.546(19) 1 calc R U P A 1
H6D H 0.505345 1.105455 0.380473 0.04 Uiso 0.546(19) 1 calc R U P A 1
C7B C 0.4691(11) 0.6279(7) 0.2634(5) 0.056(2) Uani 1 1 d . . . . .
H7D H 0.579554 0.630952 0.254484 0.084 Uiso 1 1 calc R U . . .
H7E H 0.402139 0.620087 0.224903 0.084 Uiso 1 1 calc R U . . .
H7F H 0.426843 0.565132 0.283532 0.084 Uiso 1 1 calc R U . . .
C8B C 0.2312(10) 0.9389(7) 0.3383(4) 0.0452(18) Uani 1 1 d . . . . .
H8B H 0.24581 1.006003 0.365929 0.054 Uiso 1 1 calc R U . . .
C9B C -0.1220(11) 0.9295(7) 0.2515(4) 0.048(2) Uani 1 1 d . . . . .
C10B C -0.3354(11) 0.9817(6) 0.1916(3) 0.0459(19) Uani 1 1 d . . . . .
C11B C -0.2651(11) 0.9769(8) 0.1300(4) 0.056(2) Uani 1 1 d . . . . .
H11C H -0.222473 0.912244 0.121832 0.067 Uiso 1 1 calc R U . . .
H11D H -0.175824 1.043386 0.130765 0.067 Uiso 1 1 calc R U . . .
C12B C -0.3984(14) 0.9693(10) 0.0792(4) 0.069(3) Uani 1 1 d . . . . .
H12B H -0.352383 0.967689 0.038629 0.083 Uiso 1 1 calc R U . . .
C13B C -0.4638(14) 1.0700(9) 0.0924(5) 0.073(3) Uani 1 1 d . . . . .
H13C H -0.37578 1.137527 0.094028 0.088 Uiso 1 1 calc R U . . .
H13D H -0.546741 1.066824 0.059048 0.088 Uiso 1 1 calc R U . . .
C14B C -0.5369(14) 1.0720(9) 0.1542(4) 0.069(3) Uani 1 1 d . . . . .
H14B H -0.580163 1.137233 0.162872 0.083 Uiso 1 1 calc R U . . .
C15B C -0.4023(15) 1.0807(9) 0.2040(4) 0.074(3) Uani 1 1 d . . . . .
H15C H -0.315299 1.148425 0.204586 0.089 Uiso 1 1 calc R U . . .
H15D H -0.444328 1.08489 0.24481 0.089 Uiso 1 1 calc R U . . .
C16B C -0.4683(11) 0.8790(8) 0.1896(5) 0.060(2) Uani 1 1 d . . . . .
H16C H -0.513551 0.880249 0.229755 0.072 Uiso 1 1 calc R U . . .
H16D H -0.424997 0.814524 0.181806 0.072 Uiso 1 1 calc R U . . .
C17B C -0.6013(12) 0.8694(9) 0.1384(5) 0.071(3) Uani 1 1 d . . . . .
H17B H -0.688908 0.800615 0.137023 0.085 Uiso 1 1 calc R U . . .
C18B C -0.5291(14) 0.8680(10) 0.0767(5) 0.076(3) Uani 1 1 d . . . . .
H18C H -0.48649 0.803491 0.067609 0.091 Uiso 1 1 calc R U . . .
H18D H -0.613482 0.862557 0.04336 0.091 Uiso 1 1 calc R U . . .
C19B C -0.6689(13) 0.9700(10) 0.1523(5) 0.072(3) Uani 1 1 d . . . . .
H19C H -0.755291 0.965128 0.119906 0.086 Uiso 1 1 calc R U . . .
H19D H -0.714945 0.971377 0.192292 0.086 Uiso 1 1 calc R U . . .
N1B N 0.6021(9) 0.7875(6) 0.3396(3) 0.0515(17) Uani 1 1 d . . . . .
H1N H 0.682298 0.757315 0.339589 0.062 Uiso 1 1 calc R U . . .
N2B N 0.1024(8) 0.9031(5) 0.3010(3) 0.0451(16) Uani 1 1 d . . . . .
N3B N -0.0005(9) 0.9681(5) 0.2998(3) 0.0483(17) Uani 1 1 d . . . . .
H3B H 0.00934 1.028087 0.326834 0.058 Uiso 1 1 calc R U . . .
N4B N -0.2089(9) 0.9975(6) 0.2423(3) 0.0527(18) Uani 1 1 d . . . . .
H4N H -0.189109 1.058643 0.269346 0.063 Uiso 1 1 calc R U . . .
O1B O 0.4806(15) 1.0738(9) 0.4638(6) 0.061(4) Uani 0.546(19) 1 d . . P A 1
H1B H 0.525405 1.04526 0.488797 0.092 Uiso 0.546(19) 1 calc R U P A 1
O1C O 0.673(3) 1.0814(14) 0.4390(7) 0.075(6) Uani 0.454(19) 1 d . . P A 2
H1C H 0.731211 1.073284 0.410543 0.112 Uiso 0.454(19) 1 calc R U P A 2
C6C C 0.511(7) 1.036(4) 0.416(3) 0.068(15) Uani 0.454(19) 1 d . . P A 2
H6E H 0.472691 1.087634 0.394329 0.082 Uiso 0.454(19) 1 calc R U P A 2
H6F H 0.444451 1.020927 0.450298 0.082 Uiso 0.454(19) 1 calc R U P A 2
O2B O 0.2052(6) 0.7165(4) 0.2714(3) 0.0483(14) Uani 1 1 d . . . . .
O3B O -0.1451(7) 0.8349(4) 0.2218(3) 0.0502(14) Uani 1 1 d . . . . .
Cl1B Cl -0.0802(3) 0.61892(18) 0.17119(10) 0.0668(7) Uani 1 1 d . . . . .
Cl2B Cl -0.1236(3) 0.68429(18) 0.34177(10) 0.0539(5) Uani 1 1 d . . . . .
Cu2 Cu 0.01365(14) 0.75943(9) 0.24818(5) 0.0446(3) Uani 1 1 d . . . . .
C1 C 0.3353(14) 0.5986(9) 0.7364(5) 0.075(3) Uani 1 1 d D . . . .
H1J H 0.41357 0.619156 0.772874 0.112 Uiso 1 1 calc R U . . .
H1K H 0.257273 0.528943 0.738099 0.112 Uiso 1 1 calc R U . . .
H1L H 0.279342 0.65558 0.735327 0.112 Uiso 1 1 calc R U . . .
O1 O 0.4167(9) 0.5874(5) 0.6824(3) 0.0670(17) Uani 1 1 d D . . . .
H1 H 0.485655 0.646496 0.681472 0.1 Uiso 1 1 calc R U . . .
C2 C 0.067(3) 1.056(2) 0.4793(13) 0.104(8) Uiso 0.5 1 d D . P B 1
H2J H 0.069361 1.083215 0.522514 0.156 Uiso 0.5 1 d R U P B 1
H2K H 0.077654 0.982891 0.473595 0.156 Uiso 0.5 1 d R U P B 1
H2L H -0.033089 1.056454 0.458671 0.156 Uiso 0.5 1 d R U P B 1
O2 O 0.188(2) 1.1254(14) 0.4501(8) 0.096(5) Uiso 0.5 1 d D . P B 1
H2 H 0.265728 1.147618 0.475914 0.144 Uiso 0.5 1 d R U P B 1



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1A O2A 1.286(9) . ?
C1A C5A 1.416(11) . ?
C1A C2A 1.432(10) . ?
C2A C3A 1.410(11) . ?
C2A C8A 1.448(11) . ?
C3A C4A 1.360(11) . ?
C3A C6A 1.515(10) . ?
C4A N1A 1.348(10) . ?
C5A N1A 1.341(10) . ?
C5A C7A 1.495(10) . ?
C6A O1A 1.423(12) . ?
C8A N2A 1.283(9) . ?
C9A O3A 1.259(9) . ?
C9A N4A 1.318(10) . ?
C9A N3A 1.376(10) . ?
C10A N4A 1.469(10) . ?
C10A C16A 1.492(14) . ?
C10A C11A 1.532(12) . ?
C10A C15A 1.537(11) . ?
C11A C12A 1.547(14) . ?
C12A C18A 1.497(19) . ?
C12A C13A 1.545(15) . ?
C13A C14A 1.538(16) . ?
C14A C19A 1.514(18) . ?
C14A C15A 1.550(13) . ?
C16A C17A 1.547(14) . ?
C17A C18A 1.498(18) . ?
C17A C19A 1.521(17) . ?
N2A N3A 1.371(9) . ?
N2A Cu1 1.979(6) . ?
O2A Cu1 1.932(5) . ?
O3A Cu1 1.985(5) . ?
Cl1A Cu1 2.2591(19) . ?
Cl2A Cu1 2.539(3) . ?
C1B O2B 1.295(10) . ?
C1B C5B 1.406(11) . ?
C1B C2B 1.424(11) . ?
C2B C3B 1.391(13) . ?
C2B C8B 1.457(10) . ?
C3B C4B 1.383(12) . ?
C3B C6C 1.42(5) . ?
C3B C6B 1.59(4) . ?
C4B N1B 1.345(12) . ?
C5B N1B 1.322(11) . ?
C5B C7B 1.509(12) . ?
C6B O1B 1.39(4) . ?
C8B N2B 1.286(11) . ?
C9B O3B 1.248(9) . ?
C9B N4B 1.325(10) . ?
C9B N3B 1.391(11) . ?
C10B N4B 1.477(10) . ?
C10B C16B 1.502(13) . ?
C10B C11B 1.521(12) . ?
C10B C15B 1.524(10) . ?
C11B C12B 1.540(13) . ?
C12B C18B 1.479(17) . ?
C12B C13B 1.537(14) . ?
C13B C14B 1.536(15) . ?
C14B C19B 1.493(17) . ?
C14B C15B 1.530(13) . ?
C16B C17B 1.537(14) . ?
C17B C18B 1.532(16) . ?
C17B C19B 1.548(14) . ?
N2B N3B 1.373(8) . ?
N2B Cu2 1.963(7) . ?
O1C C6C 1.40(5) . ?
O2B Cu2 1.949(5) . ?
O3B Cu2 1.990(5) . ?
Cl1B Cu2 2.223(2) . ?
Cl2B Cu2 2.632(2) . ?
C1 O1 1.427(12) . ?
C2 O2 1.442(19) . ?
C2 C2 1.98(4) 2_576 ?

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
O2A C1A C5A 116.7(6) . . ?
O2A C1A C2A 126.2(7) . . ?
C5A C1A C2A 117.0(7) . . ?
C3A C2A C1A 119.7(7) . . ?
C3A C2A C8A 118.5(6) . . ?
C1A C2A C8A 121.8(7) . . ?
C4A C3A C2A 119.6(7) . . ?
C4A C3A C6A 119.0(7) . . ?
C2A C3A C6A 121.4(7) . . ?
N1A C4A C3A 120.3(7) . . ?
N1A C5A C1A 119.9(7) . . ?
N1A C5A C7A 118.6(7) . . ?
C1A C5A C7A 121.5(7) . . ?
O1A C6A C3A 111.9(7) . . ?
N2A C8A C2A 122.7(6) . . ?
O3A C9A N4A 125.1(7) . . ?
O3A C9A N3A 118.0(7) . . ?
N4A C9A N3A 116.9(6) . . ?
N4A C10A C16A 110.3(8) . . ?
N4A C10A C11A 111.7(7) . . ?
C16A C10A C11A 109.8(8) . . ?
N4A C10A C15A 106.9(6) . . ?
C16A C10A C15A 109.7(8) . . ?
C11A C10A C15A 108.3(8) . . ?
C10A C11A C12A 108.4(8) . . ?
C18A C12A C13A 111.5(10) . . ?
C18A C12A C11A 110.3(10) . . ?
C13A C12A C11A 109.2(9) . . ?
C14A C13A C12A 107.6(9) . . ?
C19A C14A C13A 111.0(9) . . ?
C19A C14A C15A 108.8(9) . . ?
C13A C14A C15A 108.3(9) . . ?
C10A C15A C14A 109.9(7) . . ?
C10A C16A C17A 109.6(9) . . ?
C18A C17A C19A 111.9(11) . . ?
C18A C17A C16A 109.6(9) . . ?
C19A C17A C16A 108.8(9) . . ?
C12A C18A C17A 108.6(9) . . ?
C14A C19A C17A 109.0(9) . . ?
C5A N1A C4A 123.4(7) . . ?
C8A N2A N3A 118.7(6) . . ?
C8A N2A Cu1 129.9(5) . . ?
N3A N2A Cu1 111.4(4) . . ?
N2A N3A C9A 115.1(6) . . ?
C9A N4A C10A 127.8(6) . . ?
C1A O2A Cu1 127.9(5) . . ?
C9A O3A Cu1 114.1(5) . . ?
O2A Cu1 N2A 89.9(2) . . ?
O2A Cu1 O3A 163.7(3) . . ?
N2A Cu1 O3A 80.6(2) . . ?
O2A Cu1 Cl1A 93.30(16) . . ?
N2A Cu1 Cl1A 160.6(2) . . ?
O3A Cu1 Cl1A 91.55(15) . . ?
O2A Cu1 Cl2A 95.99(19) . . ?
N2A Cu1 Cl2A 98.8(2) . . ?
O3A Cu1 Cl2A 98.5(2) . . ?
Cl1A Cu1 Cl2A 99.90(8) . . ?
O2B C1B C5B 116.6(7) . . ?
O2B C1B C2B 126.4(7) . . ?
C5B C1B C2B 117.0(8) . . ?
C3B C2B C1B 120.6(7) . . ?
C3B C2B C8B 118.2(7) . . ?
C1B C2B C8B 121.0(8) . . ?
C4B C3B C2B 118.8(8) . . ?
C4B C3B C6C 122(3) . . ?
C2B C3B C6C 119(3) . . ?
C4B C3B C6B 116.5(13) . . ?
C2B C3B C6B 124.1(12) . . ?
N1B C4B C3B 119.3(9) . . ?
N1B C5B C1B 119.8(8) . . ?
N1B C5B C7B 117.2(7) . . ?
C1B C5B C7B 122.7(8) . . ?
O1B C6B C3B 111.3(18) . . ?
N2B C8B C2B 123.5(7) . . ?
O3B C9B N4B 125.1(8) . . ?
O3B C9B N3B 119.5(6) . . ?
N4B C9B N3B 115.4(7) . . ?
N4B C10B C16B 112.2(7) . . ?
N4B C10B C11B 110.5(7) . . ?
C16B C10B C11B 108.8(7) . . ?
N4B C10B C15B 105.8(6) . . ?
C16B C10B C15B 109.5(8) . . ?
C11B C10B C15B 110.0(7) . . ?
C10B C11B C12B 108.7(7) . . ?
C18B C12B C13B 110.1(9) . . ?
C18B C12B C11B 109.9(8) . . ?
C13B C12B C11B 109.5(8) . . ?
C14B C13B C12B 109.4(8) . . ?
C19B C14B C15B 110.5(9) . . ?
C19B C14B C13B 110.1(9) . . ?
C15B C14B C13B 107.4(9) . . ?
C10B C15B C14B 110.3(8) . . ?
C10B C16B C17B 110.2(7) . . ?
C18B C17B C16B 108.9(8) . . ?
C18B C17B C19B 109.6(8) . . ?
C16B C17B C19B 108.6(9) . . ?
C12B C18B C17B 109.7(8) . . ?
C14B C19B C17B 109.3(8) . . ?
C5B N1B C4B 124.4(7) . . ?
C8B N2B N3B 118.2(7) . . ?
C8B N2B Cu2 129.8(5) . . ?
N3B N2B Cu2 111.8(5) . . ?
N2B N3B C9B 113.1(6) . . ?
C9B N4B C10B 126.8(7) . . ?
O1C C6C C3B 107(4) . . ?
C1B O2B Cu2 128.0(5) . . ?
C9B O3B Cu2 113.0(5) . . ?
O2B Cu2 N2B 90.1(2) . . ?
O2B Cu2 O3B 166.7(2) . . ?
N2B Cu2 O3B 80.8(2) . . ?
O2B Cu2 Cl1B 95.18(18) . . ?
N2B Cu2 Cl1B 166.9(2) . . ?
O3B Cu2 Cl1B 91.82(17) . . ?
O2B Cu2 Cl2B 90.30(18) . . ?
N2B Cu2 Cl2B 89.5(2) . . ?
O3B Cu2 Cl2B 99.23(19) . . ?
Cl1B Cu2 Cl2B 102.46(10) . . ?
O2 C2 C2 168(3) . 2_576 ?



# END of CIF
####################################################################### 
# 
# 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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1563401'
_audit_update_record             
;
2018-04-23 deposited with the CCDC.
2018-04-25 downloaded from the CCDC.
;

_audit_creation_date             2018-04-23T17:45:11-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C36 H44 Cl2 Cu2 N6 O4, H2 O'
_chemical_formula_sum            'C36 H46 Cl2 Cu2 N6 O5'
_chemical_formula_weight         840.77
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.3255(5)
_cell_length_b                   9.7556(5)
_cell_length_c                   14.3516(9)
_cell_angle_alpha                101.145(5)
_cell_angle_beta                 90.371(5)
_cell_angle_gamma                108.493(6)
_cell_volume                     951.79(11)
_cell_formula_units_Z            1
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    3006
_cell_measurement_theta_min      4.86
_cell_measurement_theta_max      62.6
_cell_measurement_wavelength     1.5418

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             436

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    3.073
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
        (compiled Aug 13 2014,18:06:01)
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.652
_exptl_absorpt_correction_T_max  1

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'sealed X-ray tube'
_diffrn_ambient_temperature      190(2)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.07
_diffrn_orient_matrix_ub_11      0.043309
_diffrn_orient_matrix_ub_12      -0.084673
_diffrn_orient_matrix_ub_13      -0.094855
_diffrn_orient_matrix_ub_21      -0.146006
_diffrn_orient_matrix_ub_22      0.046285
_diffrn_orient_matrix_ub_23      -0.053754
_diffrn_orient_matrix_ub_31      0.161995
_diffrn_orient_matrix_ub_32      0.140156
_diffrn_orient_matrix_ub_33      -0.01212
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  
'Agilent Technologies Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_number            6829
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         4.885
_diffrn_reflns_theta_max         62.489
_diffrn_reflns_theta_full        62.489
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_reflns_Friedel_coverage         0
_reflns_number_total             3004
_reflns_number_gt                2709
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
'CrysalisPro  Version 1.171.37.35 (Agilent Technologies, 2014)'
_computing_cell_refinement       
'CrysalisPro  Version 1.171.37.35 (Agilent Technologies, 2014)'
_computing_data_reduction        
'CrysalisPro  Version 1.171.37.35 (Agilent Technologies, 2014)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     'direct - structure invariant direct methods'
_atom_sites_solution_secondary   'direct - structure invariant direct methods'
_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0592P)²+0.7891P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3004
_refine_ls_number_parameters     236
_refine_ls_number_restraints     1
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_ref         0.1127
_refine_ls_wR_factor_gt          0.1081
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.694
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.074

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1852(4) -0.0639(3) -0.1067(2) 0.0301(6) Uani 1 1 d . . . . .
C2 C 0.0838(4) 0.0381(3) -0.10443(19) 0.0291(6) Uani 1 1 d . . . . .
C3 C -0.0913(4) -0.0051(3) -0.1604(2) 0.0353(6) Uani 1 1 d . . . . .
H3 H -0.160425 0.062934 -0.158092 0.042 Uiso 1 1 calc R U . . .
C4 C -0.1653(5) -0.1425(3) -0.2184(2) 0.0402(7) Uani 1 1 d . . . . .
H4 H -0.282293 -0.168823 -0.256694 0.048 Uiso 1 1 calc R U . . .
C5 C -0.0657(5) -0.2420(4) -0.2196(2) 0.0447(8) Uani 1 1 d . . . . .
H5 H -0.115365 -0.337816 -0.25892 0.054 Uiso 1 1 calc R U . . .
C6 C 0.1050(5) -0.2035(3) -0.1645(2) 0.0418(7) Uani 1 1 d . . . . .
H6 H 0.169591 -0.274276 -0.166006 0.05 Uiso 1 1 calc R U . . .
C7 C 0.1422(4) 0.1858(3) -0.0461(2) 0.0305(6) Uani 1 1 d . . . . .
H7 H 0.058906 0.243085 -0.046576 0.037 Uiso 1 1 calc R U . . .
C8 C 0.4855(4) 0.4188(3) 0.1301(2) 0.0331(6) Uani 1 1 d . . . . .
C9 C 0.6650(5) 0.6065(3) 0.2721(2) 0.0456(8) Uani 1 1 d . . . . .
C10 C 0.8681(5) 0.6209(4) 0.2465(2) 0.0507(9) Uani 1 1 d . . . . .
H10A H 0.905058 0.685726 0.199738 0.061 Uiso 1 1 calc R U . . .
H10B H 0.875314 0.522574 0.21665 0.061 Uiso 1 1 calc R U . . .
C11 C 1.0086(7) 0.6862(5) 0.3356(3) 0.0720(13) Uani 1 1 d . . . . .
H11 H 1.143435 0.695972 0.318215 0.086 Uiso 1 1 calc R U . . .
C12 C 0.9495(8) 0.5845(5) 0.4072(3) 0.0805(15) Uani 1 1 d . . . . .
H12A H 0.954806 0.485167 0.378496 0.097 Uiso 1 1 calc R U . . .
H12B H 1.040224 0.624659 0.464704 0.097 Uiso 1 1 calc R U . . .
C13 C 0.7488(8) 0.5733(5) 0.4341(3) 0.0811(15) Uani 1 1 d . . . . .
H13 H 0.711791 0.507413 0.481053 0.097 Uiso 1 1 calc R U . . .
C14 C 0.6054(6) 0.5073(4) 0.3451(3) 0.0603(10) Uani 1 1 d . . . . .
H14A H 0.606109 0.406412 0.31702 0.072 Uiso 1 1 calc R U . . .
H14B H 0.473135 0.500804 0.363053 0.072 Uiso 1 1 calc R U . . .
C15 C 0.6546(8) 0.7601(4) 0.3165(3) 0.0743(13) Uani 1 1 d . . . . .
H15A H 0.691768 0.825873 0.270336 0.089 Uiso 1 1 calc R U . . .
H15B H 0.521009 0.752207 0.332709 0.089 Uiso 1 1 calc R U . . .
C16 C 0.7919(9) 0.8244(5) 0.4064(3) 0.0886(17) Uani 1 1 d . . . . .
H16 H 0.785227 0.924254 0.435571 0.106 Uiso 1 1 calc R U . . .
C17 C 0.7372(10) 0.7242(6) 0.4785(3) 0.103(2) Uani 1 1 d . . . . .
H17A H 0.826396 0.767453 0.536477 0.123 Uiso 1 1 calc R U . . .
H17B H 0.604451 0.715019 0.49693 0.123 Uiso 1 1 calc R U . . .
C18 C 0.9943(9) 0.8384(5) 0.3805(3) 0.0909(19) Uani 1 1 d . . . . .
H18A H 1.084032 0.882087 0.438303 0.109 Uiso 1 1 calc R U . . .
H18B H 1.032336 0.905052 0.334923 0.109 Uiso 1 1 calc R U . . .
N1 N 0.3006(3) 0.2426(2) 0.00608(16) 0.0287(5) Uani 1 1 d . . . . .
N2 N 0.3445(4) 0.3835(2) 0.05948(18) 0.0340(5) Uani 1 1 d . . . . .
H2 H 0.285966 0.445543 0.048744 0.041 Uiso 1 1 calc R U . . .
N3 N 0.5274(4) 0.5513(3) 0.18745(19) 0.0428(6) Uani 1 1 d . . . . .
H3A H 0.467803 0.61097 0.173533 0.051 Uiso 1 1 calc R U . . .
O1 O 0.3531(3) -0.03127(19) -0.05491(14) 0.0316(4) Uani 1 1 d . . . . .
O2 O 0.5682(3) 0.3261(2) 0.13919(14) 0.0353(5) Uani 1 1 d . . . . .
Cl1 Cl 0.73094(11) 0.30762(8) -0.07521(6) 0.0461(2) Uani 1 1 d . . . . .
Cu1 Cu 0.49877(5) 0.15720(4) 0.02739(3) 0.02934(17) Uani 1 1 d . . . . .
O3A O 0.528(6) 1.027(5) 0.486(3) 0.090(11) Uiso 0.099(3) 1 d . . P A -2
H3AA H 0.63447 1.089854 0.478469 0.136 Uiso 0.099(3) 1 d R U P A -2
H3AB H 0.47049 0.959694 0.438129 0.136 Uiso 0.099(3) 1 d R U P A -2
O3B O 0.406(3) 0.898(2) 0.6340(15) 0.208(8) Uiso 0.401(3) 1 d . . P B -1
H3BA H 0.497334 0.936215 0.678364 0.312 Uiso 0.401(3) 1 d R U P B -1
H3BB H 0.455384 0.890455 0.566834 0.312 Uiso 0.401(3) 1 d R U P B -1



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1 O1 1.347(3) . ?
C1 C6 1.392(4) . ?
C1 C2 1.414(4) . ?
C2 C3 1.408(4) . ?
C2 C7 1.448(4) . ?
C3 C4 1.373(5) . ?
C4 C5 1.384(5) . ?
C5 C6 1.381(5) . ?
C7 N1 1.278(4) . ?
C8 O2 1.262(4) . ?
C8 N3 1.333(4) . ?
C8 N2 1.356(4) . ?
C9 N3 1.473(4) . ?
C9 C10 1.504(5) . ?
C9 C14 1.534(5) . ?
C9 C15 1.537(5) . ?
C10 C11 1.534(5) . ?
C11 C12 1.534(6) . ?
C11 C18 1.536(7) . ?
C12 C13 1.498(8) . ?
C13 C17 1.517(8) . ?
C13 C14 1.544(6) . ?
C15 C16 1.530(7) . ?
C16 C18 1.501(8) . ?
C16 C17 1.527(7) . ?
N1 N2 1.374(3) . ?
N1 Cu1 1.938(2) . ?
O1 Cu1 1.9529(18) . ?
O1 Cu1 1.9671(18) 2_655 ?
O2 Cu1 1.9961(19) . ?
Cl1 Cu1 2.5493(8) . ?
Cu1 Cu1 3.0215(7) 2_655 ?

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
O1 C1 C6 119.6(2) . . ?
O1 C1 C2 122.7(2) . . ?
C6 C1 C2 117.8(3) . . ?
C3 C2 C1 119.0(3) . . ?
C3 C2 C7 115.7(2) . . ?
C1 C2 C7 125.2(3) . . ?
C4 C3 C2 122.0(3) . . ?
C3 C4 C5 118.5(3) . . ?
C6 C5 C4 120.8(3) . . ?
C5 C6 C1 121.8(3) . . ?
N1 C7 C2 123.0(2) . . ?
O2 C8 N3 123.4(3) . . ?
O2 C8 N2 119.4(2) . . ?
N3 C8 N2 117.2(3) . . ?
N3 C9 C10 111.8(3) . . ?
N3 C9 C14 111.0(3) . . ?
C10 C9 C14 110.4(3) . . ?
N3 C9 C15 105.8(3) . . ?
C10 C9 C15 109.1(3) . . ?
C14 C9 C15 108.5(3) . . ?
C9 C10 C11 110.4(3) . . ?
C10 C11 C12 108.9(3) . . ?
C10 C11 C18 108.5(4) . . ?
C12 C11 C18 108.9(4) . . ?
C13 C12 C11 109.6(4) . . ?
C12 C13 C17 110.7(4) . . ?
C12 C13 C14 110.1(3) . . ?
C17 C13 C14 108.8(5) . . ?
C9 C14 C13 109.0(3) . . ?
C16 C15 C9 109.0(4) . . ?
C18 C16 C17 108.9(5) . . ?
C18 C16 C15 109.3(4) . . ?
C17 C16 C15 110.7(4) . . ?
C13 C17 C16 109.0(4) . . ?
C16 C18 C11 110.3(4) . . ?
C7 N1 N2 119.2(2) . . ?
C7 N1 Cu1 129.68(19) . . ?
N2 N1 Cu1 111.05(17) . . ?
C8 N2 N1 114.4(2) . . ?
C8 N3 C9 125.6(3) . . ?
C1 O1 Cu1 127.41(16) . . ?
C1 O1 Cu1 131.35(16) . 2_655 ?
Cu1 O1 Cu1 100.85(8) . 2_655 ?
C8 O2 Cu1 111.20(18) . . ?
N1 Cu1 O1 91.79(9) . . ?
N1 Cu1 O1 166.20(9) . 2_655 ?
O1 Cu1 O1 79.15(8) . 2_655 ?
N1 Cu1 O2 80.72(9) . . ?
O1 Cu1 O2 159.53(9) . . ?
O1 Cu1 O2 104.24(8) 2_655 . ?
N1 Cu1 Cl1 92.98(7) . . ?
O1 Cu1 Cl1 107.18(6) . . ?
O1 Cu1 Cl1 99.61(6) 2_655 . ?
O2 Cu1 Cl1 92.30(6) . . ?
N1 Cu1 Cu1 130.72(7) . 2_655 ?
O1 Cu1 Cu1 39.75(5) . 2_655 ?
O1 Cu1 Cu1 39.40(5) 2_655 2_655 ?
O2 Cu1 Cu1 139.97(6) . 2_655 ?
Cl1 Cu1 Cu1 107.43(3) . 2_655 ?



# END of CIF
####################################################################### 
# 
# 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_shelx_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1563402'
_audit_update_record             
;
2018-04-23 deposited with the CCDC.
2018-04-25 downloaded from the CCDC.
;

_audit_creation_date             2018-04-23T17:39:58-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C36 H44 Fe N6 O4, Cl O4, 0.5 (C2 H6 O)'
_chemical_formula_sum            'C37 H47 Cl Fe N6 O8.50'
_chemical_formula_weight         803.1

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.0978(9)
_cell_length_b                   12.7887(10)
_cell_length_c                   14.2619(12)
_cell_angle_alpha                77.005(7)
_cell_angle_beta                 81.372(7)
_cell_angle_gamma                87.444(7)
_cell_volume                     1949.9(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    3763
_cell_measurement_theta_min      3.69
_cell_measurement_theta_max      27.09
_cell_measurement_wavelength     0

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            'clear black'
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             844

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.515
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.908
_exptl_absorpt_correction_T_max  1

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_ambient_temperature      190(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.07
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      0.041435
_diffrn_orient_matrix_ub_12      0.003079
_diffrn_orient_matrix_ub_13      -0.043512
_diffrn_orient_matrix_ub_21      -0.045423
_diffrn_orient_matrix_ub_22      0.02597
_diffrn_orient_matrix_ub_23      -0.027417
_diffrn_orient_matrix_ub_31      0.019986
_diffrn_orient_matrix_ub_32      0.050562
_diffrn_orient_matrix_ub_33      0.003905
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  
'Agilent Technologies Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_unetI/netI     0.0511
_diffrn_reflns_number            14658
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.333
_diffrn_reflns_theta_max         25
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_reflns_Friedel_coverage         0
_reflns_number_total             6843
_reflns_number_gt                5413
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysalisPro (Agilent Technologies,     )'
_computing_cell_refinement       'CrysalisPro (Agilent Technologies,     )'
_computing_data_reduction        'CrysalisPro (Agilent Technologies,     )'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0830P)²+1.5254P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         6843
_refine_ls_number_parameters     494
_refine_ls_number_restraints     6
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0733
_refine_ls_R_factor_gt           0.0566
_refine_ls_wR_factor_ref         0.1656
_refine_ls_wR_factor_gt          0.1526
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.05
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.982
_refine_diff_density_min         -0.476
_refine_diff_density_rms         0.075

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'
Fe Fe 0.3463 0.8444 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1A C 0.3088(3) 0.8338(3) 0.5999(2) 0.0302(7) Uani 1 1 d . . . . .
C1B C 0.3832(3) 0.6636(3) 0.9257(3) 0.0341(8) Uani 1 1 d . . . . .
C2A C 0.2103(3) 0.8085(3) 0.5569(3) 0.0416(9) Uani 1 1 d . . . . .
H2A H 0.18811 0.735554 0.56653 0.05 Uiso 1 1 calc R U . . .
C2B C 0.3264(3) 0.6908(3) 1.0117(3) 0.0445(9) Uani 1 1 d . . . . .
H2B H 0.326322 0.763324 1.017596 0.053 Uiso 1 1 calc R U . . .
C3A C 0.1464(3) 0.8863(4) 0.5020(3) 0.0466(10) Uani 1 1 d . . . . .
H3A H 0.080258 0.866833 0.47442 0.056 Uiso 1 1 calc R U . . .
C3B C 0.2712(3) 0.6148(4) 1.0873(3) 0.0525(11) Uani 1 1 d . . . . .
H3B H 0.231489 0.635595 1.144199 0.063 Uiso 1 1 calc R U . . .
C4A C 0.1772(3) 0.9940(4) 0.4857(3) 0.0495(10) Uani 1 1 d . . . . .
H4A H 0.132077 1.047865 0.447652 0.059 Uiso 1 1 calc R U . . .
C4B C 0.2724(4) 0.5083(4) 1.0822(3) 0.0581(12) Uani 1 1 d . . . . .
H4B H 0.23176 0.456537 1.134479 0.07 Uiso 1 1 calc R U . . .
C5A C 0.2731(3) 1.0212(3) 0.5253(3) 0.0413(9) Uani 1 1 d . . . . .
H5A H 0.294586 1.094614 0.51356 0.05 Uiso 1 1 calc R U . . .
C5B C 0.3320(4) 0.4777(3) 1.0019(3) 0.0502(10) Uani 1 1 d . . . . .
H5B H 0.335393 0.403917 0.999717 0.06 Uiso 1 1 calc R U . . .
C6A C 0.3405(3) 0.9435(3) 0.5829(2) 0.0323(8) Uani 1 1 d . . . . .
C6B C 0.3886(3) 0.5536(3) 0.9221(3) 0.0364(8) Uani 1 1 d . . . . .
C7A C 0.4382(3) 0.9782(3) 0.6225(3) 0.0324(8) Uani 1 1 d . . . . .
H7A H 0.452555 1.053088 0.610062 0.039 Uiso 1 1 calc R U . . .
C7B C 0.4568(3) 0.5158(3) 0.8424(3) 0.0372(8) Uani 1 1 d . . . . .
H7B H 0.46264 0.440438 0.847321 0.045 Uiso 1 1 calc R U . . .
C8A C 0.6810(3) 0.8881(3) 0.7497(3) 0.0311(7) Uani 1 1 d . . . . .
C8B C 0.6318(3) 0.5974(3) 0.6150(3) 0.0367(8) Uani 1 1 d . . . . .
C9A C 0.8718(3) 0.8727(3) 0.8260(2) 0.0309(7) Uani 1 1 d . . . . .
C9B C 0.7596(3) 0.6026(3) 0.4530(3) 0.0425(9) Uani 1 1 d . . . . .
C10A C 0.9423(3) 0.9577(3) 0.8557(3) 0.0403(9) Uani 1 1 d . . . . .
H10A H 0.971645 1.013783 0.7976 0.048 Uiso 1 1 calc R U . . .
H10B H 0.887675 0.992339 0.901697 0.048 Uiso 1 1 calc R U . . .
C10B C 0.8619(4) 0.6753(4) 0.4574(3) 0.0563(11) Uani 1 1 d . . . . .
H10C H 0.922534 0.633749 0.495569 0.068 Uiso 1 1 calc R U . . .
H10D H 0.828912 0.733522 0.489693 0.068 Uiso 1 1 calc R U . . .
C11A C 1.0504(3) 0.9051(3) 0.9037(3) 0.0452(9) Uani 1 1 d . . . . .
H11A H 1.096217 0.960726 0.92289 0.054 Uiso 1 1 calc R U . . .
C11B C 0.9244(4) 0.7244(5) 0.3517(4) 0.0771(17) Uani 1 1 d . . . . .
H11B H 0.990722 0.774075 0.353439 0.093 Uiso 1 1 calc R U . . .
C12A C 1.0049(4) 0.8197(4) 0.9936(3) 0.0562(11) Uani 1 1 d . . . . .
H12A H 0.949808 0.852813 1.040444 0.067 Uiso 1 1 calc R U . . .
H12B H 1.074627 0.786266 1.025716 0.067 Uiso 1 1 calc R U . . .
C12B C 0.9784(5) 0.6293(6) 0.3081(5) 0.111(3) Uani 1 1 d . . . . .
H12C H 1.022117 0.65667 0.241793 0.133 Uiso 1 1 calc R U . . .
H12D H 1.037537 0.589008 0.348623 0.133 Uiso 1 1 calc R U . . .
C13A C 0.9361(4) 0.7337(3) 0.9631(3) 0.0490(10) Uani 1 1 d . . . . .
H13A H 0.906494 0.677206 1.021988 0.059 Uiso 1 1 calc R U . . .
C13B C 0.8789(6) 0.5564(6) 0.3039(5) 0.106(3) Uani 1 1 d . . . . .
H13B H 0.913422 0.497004 0.272503 0.127 Uiso 1 1 calc R U . . .
C14A C 0.8264(3) 0.7869(3) 0.9162(3) 0.0407(9) Uani 1 1 d . . . . .
H14A H 0.779833 0.732233 0.897833 0.049 Uiso 1 1 calc R U . . .
H14B H 0.771656 0.820034 0.963203 0.049 Uiso 1 1 calc R U . . .
C14B C 0.8148(5) 0.5099(4) 0.4065(4) 0.0768(16) Uani 1 1 d . . . . .
H14C H 0.873872 0.468344 0.446405 0.092 Uiso 1 1 calc R U . . .
H14D H 0.749468 0.460842 0.403771 0.092 Uiso 1 1 calc R U . . .
C15A C 1.1346(3) 0.8536(3) 0.8306(3) 0.0458(10) Uani 1 1 d . . . . .
H15A H 1.163938 0.909303 0.772223 0.055 Uiso 1 1 calc R U . . .
H15B H 1.206282 0.820562 0.860182 0.055 Uiso 1 1 calc R U . . .
C15B C 0.8293(5) 0.7848(5) 0.2944(4) 0.0878(18) Uani 1 1 d . . . . .
H15C H 0.794758 0.843843 0.324946 0.105 Uiso 1 1 calc R U . . .
H15D H 0.867976 0.816752 0.227439 0.105 Uiso 1 1 calc R U . . .
C16A C 1.0199(3) 0.6824(3) 0.8913(3) 0.0467(10) Uani 1 1 d . . . . .
H16A H 0.975246 0.62669 0.872553 0.056 Uiso 1 1 calc R U . . .
H16B H 1.090032 0.647417 0.921936 0.056 Uiso 1 1 calc R U . . .
C16B C 0.7824(8) 0.6215(8) 0.2446(5) 0.141(4) Uani 1 1 d . . . . .
H16C H 0.821409 0.651589 0.177299 0.169 Uiso 1 1 calc R U . . .
H16D H 0.716815 0.572966 0.241416 0.169 Uiso 1 1 calc R U . . .
C17A C 0.9561(3) 0.8206(3) 0.7536(3) 0.0360(8) Uani 1 1 d . . . . .
H17A H 0.985083 0.87578 0.694697 0.043 Uiso 1 1 calc R U . . .
H17B H 0.910856 0.766029 0.733957 0.043 Uiso 1 1 calc R U . . .
C17B C 0.6678(4) 0.6669(5) 0.3922(3) 0.0697(14) Uani 1 1 d . . . . .
H17C H 0.599886 0.619877 0.390634 0.084 Uiso 1 1 calc R U . . .
H17D H 0.633504 0.726399 0.422229 0.084 Uiso 1 1 calc R U . . .
C18A C 1.0654(3) 0.7676(3) 0.8012(3) 0.0403(9) Uani 1 1 d . . . . .
H18A H 1.120781 0.733737 0.754076 0.048 Uiso 1 1 calc R U . . .
C18B C 0.7282(6) 0.7114(6) 0.2904(4) 0.094(2) Uani 1 1 d . . . . .
H18B H 0.667306 0.7525 0.250963 0.113 Uiso 1 1 calc R U . . .
Fe1 Fe 0.50388(4) 0.74556(3) 0.72103(4) 0.02932(17) Uani 1 1 d . . . . .
N1A N 0.5083(2) 0.9143(2) 0.6743(2) 0.0284(6) Uani 1 1 d . . . . .
N1B N 0.5102(2) 0.5769(2) 0.7650(2) 0.0329(6) Uani 1 1 d . . . . .
N2A N 0.5975(2) 0.9588(2) 0.7092(2) 0.0346(7) Uani 1 1 d . . . . .
H2J H 0.600686 1.028244 0.705731 0.042 Uiso 1 1 calc R U . . .
N2B N 0.5773(3) 0.5296(2) 0.6968(2) 0.0462(8) Uani 1 1 d . . . . .
H2K H 0.584741 0.459391 0.705217 0.055 Uiso 1 1 calc R U . . .
N3A N 0.7696(2) 0.9304(2) 0.7809(2) 0.0340(7) Uani 1 1 d . . . . .
H3K H 0.767469 1.000567 0.774026 0.041 Uiso 1 1 calc R U . . .
N3B N 0.6994(3) 0.5506(2) 0.5506(2) 0.0492(9) Uani 1 1 d . . . . .
H3J H 0.709196 0.480608 0.568235 0.059 Uiso 1 1 calc R U . . .
O1A O 0.3660(2) 0.75672(18) 0.65471(19) 0.0380(6) Uani 1 1 d . . . . .
O1B O 0.4312(2) 0.73887(19) 0.85185(18) 0.0394(6) Uani 1 1 d . . . . .
O2A O 0.66833(19) 0.79003(17) 0.75419(18) 0.0352(6) Uani 1 1 d . . . . .
O2B O 0.6158(2) 0.69564(17) 0.60686(17) 0.0344(5) Uani 1 1 d . . . . .
Cl1 Cl 0.33719(9) 0.75607(7) 0.30060(9) 0.0528(3) Uani 1 1 d . . . . .
O1 O 0.4201(3) 0.7021(2) 0.2406(3) 0.0690(9) Uani 1 1 d . . . . .
O2 O 0.4053(3) 0.8139(2) 0.3498(2) 0.0552(8) Uani 1 1 d . . . . .
O3 O 0.2616(3) 0.8298(2) 0.2431(3) 0.0824(11) Uani 1 1 d . . . . .
O4 O 0.2629(3) 0.6775(2) 0.3690(3) 0.0843(12) Uani 1 1 d . . . . .
C1 C 0.4685(11) 0.0626(11) 0.9323(10) 0.065(4) Uiso 0.369(7) 1 d D . P A -1
H1P H 0.539973 0.074427 0.880703 0.079 Uiso 0.369(7) 1 d R U P A -1
H1O H 0.449181 0.131705 0.951845 0.079 Uiso 0.369(7) 1 d R U P A -1
C2 C 0.3667(9) 0.0373(9) 0.8869(8) 0.043(3) Uiso 0.369(7) 1 d D . P A -1
H2C H 0.351803 0.094934 0.831609 0.065 Uiso 0.369(7) 1 d R U P A -1
H2D H 0.385148 -0.029662 0.864863 0.065 Uiso 0.369(7) 1 d R U P A -1
H2E H 0.294033 0.027822 0.936257 0.065 Uiso 0.369(7) 1 d R U P A -1
O5 O 0.492(3) -0.011(2) 1.0211(17) 0.183(8) Uiso 0.369(7) 1 d D . P A -1
H5C H 0.557347 0.014531 1.046474 0.275 Uiso 0.369(7) 1 d R U P A -1
C1C C 0.581(2) 0.024(2) 0.9747(12) 0.023(6) Uiso 0.131(7) 1 d D . P A -2
H1X H 0.614729 -0.034425 0.943554 0.028 Uiso 0.131(7) 1 d R U P A -2
H1Y H 0.625909 0.090322 0.940856 0.028 Uiso 0.131(7) 1 d R U P A -2
C2C C 0.452(4) -0.001(8) 0.973(3) 0.20(5) Uiso 0.131(7) 1 d D . P A -2
H2X H 0.446175 0.016224 0.902768 0.297 Uiso 0.131(7) 1 d R U P A -2
H2Y H 0.40611 -0.066417 1.003965 0.297 Uiso 0.131(7) 1 d R U P A -2
H2Z H 0.417311 0.058586 1.001262 0.297 Uiso 0.131(7) 1 d R U P A -2
O5C O 0.6177(12) 0.0012(13) 1.0710(11) 0.019(5) Uiso 0.131(7) 1 d D . P A -2
H5M H 0.568332 -0.04596 1.103279 0.029 Uiso 0.131(7) 1 d R U P A -2



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1A O1A 1.317(4) . ?
C1A C2A 1.413(5) . ?
C1A C6A 1.420(5) . ?
C1B O1B 1.319(4) . ?
C1B C2B 1.402(5) . ?
C1B C6B 1.418(5) . ?
C2A C3A 1.364(6) . ?
C2B C3B 1.365(6) . ?
C3A C4A 1.393(6) . ?
C3B C4B 1.380(6) . ?
C4A C5A 1.370(5) . ?
C4B C5B 1.362(6) . ?
C5A C6A 1.404(5) . ?
C5B C6B 1.405(5) . ?
C6A C7A 1.425(5) . ?
C6B C7B 1.434(5) . ?
C7A N1A 1.289(4) . ?
C7B N1B 1.279(4) . ?
C8A O2A 1.254(4) . ?
C8A N3A 1.321(4) . ?
C8A N2A 1.364(4) . ?
C8B O2B 1.242(4) . ?
C8B N3B 1.328(4) . ?
C8B N2B 1.364(5) . ?
C9A N3A 1.474(4) . ?
C9A C14A 1.528(5) . ?
C9A C17A 1.532(4) . ?
C9A C10A 1.535(5) . ?
C9B N3B 1.473(5) . ?
C9B C10B 1.516(5) . ?
C9B C17B 1.529(6) . ?
C9B C14B 1.545(6) . ?
C10A C11A 1.527(5) . ?
C10B C11B 1.563(7) . ?
C11A C12A 1.523(6) . ?
C11A C15A 1.535(5) . ?
C11B C15B 1.510(8) . ?
C11B C12B 1.547(7) . ?
C12A C13A 1.540(6) . ?
C12B C13B 1.493(8) . ?
C13A C16A 1.519(5) . ?
C13A C14A 1.536(5) . ?
C13B C14B 1.529(8) . ?
C13B C16B 1.559(11) . ?
C15A C18A 1.534(5) . ?
C15B C18B 1.509(7) . ?
C16A C18A 1.522(5) . ?
C16B C18B 1.507(10) . ?
C17A C18A 1.536(5) . ?
C17B C18B 1.500(7) . ?
Fe1 O1A 1.900(2) . ?
Fe1 O1B 1.903(2) . ?
Fe1 O2A 2.086(2) . ?
Fe1 O2B 2.096(2) . ?
Fe1 N1B 2.108(3) . ?
Fe1 N1A 2.111(3) . ?
N1A N2A 1.370(4) . ?
N1B N2B 1.369(4) . ?
Cl1 O1 1.424(3) . ?
Cl1 O4 1.426(3) . ?
Cl1 O3 1.433(3) . ?
Cl1 O2 1.433(3) . ?
C1 O5 1.446(10) . ?
C1 C2 1.464(9) . ?
C1C O5C 1.457(10) . ?
C1C C2C 1.486(10) . ?

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
O1A C1A C2A 119.7(3) . . ?
O1A C1A C6A 122.6(3) . . ?
C2A C1A C6A 117.7(3) . . ?
O1B C1B C2B 120.2(3) . . ?
O1B C1B C6B 122.0(3) . . ?
C2B C1B C6B 117.7(3) . . ?
C3A C2A C1A 121.5(4) . . ?
C3B C2B C1B 121.2(4) . . ?
C2A C3A C4A 120.8(4) . . ?
C2B C3B C4B 120.9(4) . . ?
C5A C4A C3A 119.2(4) . . ?
C5B C4B C3B 119.8(4) . . ?
C4A C5A C6A 121.7(4) . . ?
C4B C5B C6B 121.0(4) . . ?
C5A C6A C1A 119.1(3) . . ?
C5A C6A C7A 118.5(3) . . ?
C1A C6A C7A 122.5(3) . . ?
C5B C6B C1B 119.2(3) . . ?
C5B C6B C7B 118.4(3) . . ?
C1B C6B C7B 122.2(3) . . ?
N1A C7A C6A 124.1(3) . . ?
N1B C7B C6B 124.2(3) . . ?
O2A C8A N3A 125.6(3) . . ?
O2A C8A N2A 118.5(3) . . ?
N3A C8A N2A 115.9(3) . . ?
O2B C8B N3B 125.8(3) . . ?
O2B C8B N2B 118.7(3) . . ?
N3B C8B N2B 115.5(3) . . ?
N3A C9A C14A 111.5(3) . . ?
N3A C9A C17A 111.1(3) . . ?
C14A C9A C17A 109.4(3) . . ?
N3A C9A C10A 105.9(3) . . ?
C14A C9A C10A 109.3(3) . . ?
C17A C9A C10A 109.5(3) . . ?
N3B C9B C10B 112.1(3) . . ?
N3B C9B C17B 111.0(3) . . ?
C10B C9B C17B 109.5(4) . . ?
N3B C9B C14B 105.4(3) . . ?
C10B C9B C14B 108.6(3) . . ?
C17B C9B C14B 110.2(4) . . ?
C11A C10A C9A 109.8(3) . . ?
C9B C10B C11B 109.3(3) . . ?
C12A C11A C10A 109.6(3) . . ?
C12A C11A C15A 109.9(3) . . ?
C10A C11A C15A 108.7(3) . . ?
C15B C11B C12B 111.2(5) . . ?
C15B C11B C10B 108.7(4) . . ?
C12B C11B C10B 106.6(5) . . ?
C11A C12A C13A 109.1(3) . . ?
C13B C12B C11B 110.0(5) . . ?
C16A C13A C14A 109.9(3) . . ?
C16A C13A C12A 110.2(3) . . ?
C14A C13A C12A 108.8(3) . . ?
C12B C13B C14B 109.9(5) . . ?
C12B C13B C16B 109.5(6) . . ?
C14B C13B C16B 107.8(5) . . ?
C9A C14A C13A 109.2(3) . . ?
C13B C14B C9B 109.2(5) . . ?
C18A C15A C11A 110.0(3) . . ?
C18B C15B C11B 111.1(5) . . ?
C13A C16A C18A 109.8(3) . . ?
C18B C16B C13B 111.1(5) . . ?
C9A C17A C18A 109.5(3) . . ?
C18B C17B C9B 110.3(4) . . ?
C16A C18A C15A 109.5(3) . . ?
C16A C18A C17A 109.3(3) . . ?
C15A C18A C17A 108.9(3) . . ?
C17B C18B C16B 110.0(6) . . ?
C17B C18B C15B 108.7(4) . . ?
C16B C18B C15B 108.7(5) . . ?
O1A Fe1 O1B 102.43(11) . . ?
O1A Fe1 O2A 157.42(10) . . ?
O1B Fe1 O2A 89.75(10) . . ?
O1A Fe1 O2B 91.71(10) . . ?
O1B Fe1 O2B 156.55(10) . . ?
O2A Fe1 O2B 83.71(9) . . ?
O1A Fe1 N1B 97.70(11) . . ?
O1B Fe1 N1B 84.23(10) . . ?
O2A Fe1 N1B 102.45(10) . . ?
O2B Fe1 N1B 75.31(10) . . ?
O1A Fe1 N1A 84.54(10) . . ?
O1B Fe1 N1A 97.62(10) . . ?
O2A Fe1 N1A 74.94(9) . . ?
O2B Fe1 N1A 102.33(10) . . ?
N1B Fe1 N1A 176.75(10) . . ?
C7A N1A N2A 117.9(3) . . ?
C7A N1A Fe1 129.6(2) . . ?
N2A N1A Fe1 112.42(19) . . ?
C7B N1B N2B 118.0(3) . . ?
C7B N1B Fe1 129.1(2) . . ?
N2B N1B Fe1 112.8(2) . . ?
C8A N2A N1A 115.4(3) . . ?
C8B N2B N1B 116.2(3) . . ?
C8A N3A C9A 127.0(3) . . ?
C8B N3B C9B 127.3(3) . . ?
C1A O1A Fe1 136.5(2) . . ?
C1B O1B Fe1 136.2(2) . . ?
C8A O2A Fe1 116.4(2) . . ?
C8B O2B Fe1 117.0(2) . . ?
O1 Cl1 O4 108.1(2) . . ?
O1 Cl1 O3 110.5(2) . . ?
O4 Cl1 O3 109.5(2) . . ?
O1 Cl1 O2 108.84(19) . . ?
O4 Cl1 O2 110.6(2) . . ?
O3 Cl1 O2 109.24(18) . . ?
O5 C1 C2 116.9(10) . . ?
O5C C1C C2C 115.1(11) . . ?



# END of CIF
