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

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 974887'
_audit_update_record             
;
2015-02-13 deposited with the CCDC.
2015-02-27 downloaded from the CCDC.
;

#------------------ AUDIT DETAILS -------------------------------------------#

_audit_creation_date             2013-02-04
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#------------------  SECTION 2. COMPOUND(S) DETAILS -------------------------#

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#
_chemical_name_systematic        '[Cu(pap)Cl2]'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H18 Cl2 Cu N4'
_chemical_formula_weight         448.82

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'
N N 0.0061 0.0033 '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'
#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   8.221(5)
_cell_length_b                   14.202(5)
_cell_length_c                   16.421(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 97.171(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     1902.2(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.567
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             916
#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#
_exptl_absorpt_coefficient_mu    1.442
_exptl_crystal_description       prism
_exptl_crystal_colour            green
_exptl_absorpt_correction_T_min  0.54746
_exptl_absorpt_correction_T_max  1.00000
#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            25442
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_av_sigmaI/netI    0.0234
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.90
_diffrn_reflns_theta_max         25.34
_reflns_number_total             3470
_reflns_number_gt                2771
_reflns_threshold_expression     >2sigma(I)
#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0808P)²+2.6927P] where P=(Fo²+2Fc²)/3'
#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3470
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0694
_refine_ls_R_factor_gt           0.0531
_refine_ls_wR_factor_ref         0.1601
_refine_ls_wR_factor_gt          0.1454
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0.14681(8) 0.23906(4) 0.13038(3) 0.0533(2) Uani 1 1 d . . .
Cl1 Cl 0.39550(16) 0.14341(9) 0.10678(9) 0.0687(4) Uani 1 1 d . . .
Cl2 Cl 0.0154(2) 0.17025(12) 0.23107(7) 0.0894(6) Uani 1 1 d . . .
N1 N 0.0067(4) 0.1744(2) 0.0388(2) 0.0434(8) Uani 1 1 d . . .
C1 C -0.1045(6) 0.1063(3) 0.0444(3) 0.0533(11) Uani 1 1 d . . .
H1 H -0.1313 0.0906 0.0961 0.064 Uiso 1 1 calc R . .
C2 C -0.1806(6) 0.0586(4) -0.0224(3) 0.0627(14) Uani 1 1 d . . .
H2 H -0.2562 0.0113 -0.0161 0.075 Uiso 1 1 calc R . .
C3 C -0.1429(6) 0.0823(4) -0.0982(3) 0.0627(14) Uani 1 1 d . . .
H3 H -0.1917 0.0506 -0.1444 0.075 Uiso 1 1 calc R . .
C4 C -0.0312(6) 0.1539(4) -0.1060(3) 0.0566(12) Uani 1 1 d . . .
H4 H -0.0058 0.1715 -0.1575 0.068 Uiso 1 1 calc R . .
C5 C 0.0417(5) 0.1989(3) -0.0362(3) 0.0424(9) Uani 1 1 d . . .
C6 C 0.1643(6) 0.2765(3) -0.0382(3) 0.0456(10) Uani 1 1 d . . .
H07A H 0.2725 0.2503 -0.0406 0.055 Uiso 1 1 calc R . .
H07B H 0.1356 0.3154 -0.0864 0.055 Uiso 1 1 calc R . .
N2 N 0.1642(4) 0.3332(2) 0.0361(2) 0.0389(7) Uani 1 1 d . . .
C7 C 0.1964(5) 0.4227(3) 0.0341(2) 0.0387(9) Uani 1 1 d . . .
C8 C 0.2598(5) 0.4842(3) -0.0278(3) 0.0436(10) Uani 1 1 d . . .
C9 C 0.3095(6) 0.4644(4) -0.1044(3) 0.0572(12) Uani 1 1 d . . .
H9 H 0.3055 0.4035 -0.1253 0.069 Uiso 1 1 calc R . .
C10 C 0.3652(7) 0.5393(5) -0.1482(4) 0.0744(17) Uani 1 1 d . . .
H10 H 0.3959 0.5287 -0.2000 0.089 Uiso 1 1 calc R . .
C11 C 0.3758(7) 0.6297(5) -0.1155(4) 0.0804(19) Uani 1 1 d . . .
H11 H 0.4138 0.6785 -0.1459 0.096 Uiso 1 1 calc R . .
C12 C 0.3316(7) 0.6484(4) -0.0399(4) 0.0712(16) Uani 1 1 d . . .
H12 H 0.3400 0.7089 -0.0181 0.085 Uiso 1 1 calc R . .
C13 C 0.2739(6) 0.5745(3) 0.0033(3) 0.0528(11) Uani 1 1 d . . .
C14 C 0.2232(6) 0.5769(3) 0.0872(3) 0.0540(11) Uani 1 1 d . . .
H14A H 0.3142 0.5937 0.1281 0.065 Uiso 1 1 calc R . .
H14B H 0.1338 0.6207 0.0904 0.065 Uiso 1 1 calc R . .
N3 N 0.1714(4) 0.4803(2) 0.0975(2) 0.0436(8) Uani 1 1 d . . .
C15 C 0.1015(5) 0.4502(3) 0.1702(3) 0.0455(10) Uani 1 1 d . . .
H15A H 0.0155 0.4045 0.1547 0.055 Uiso 1 1 calc R . .
H15B H 0.0526 0.5039 0.1943 0.055 Uiso 1 1 calc R . .
C16 C 0.2282(5) 0.4075(3) 0.2322(2) 0.0419(9) Uani 1 1 d . . .
C17 C 0.3037(6) 0.4600(4) 0.2979(3) 0.0557(12) Uani 1 1 d . . .
H17 H 0.2749 0.5225 0.3047 0.067 Uiso 1 1 calc R . .
C18 C 0.4223(7) 0.4173(4) 0.3530(3) 0.0641(14) Uani 1 1 d . . .
H18 H 0.4726 0.4502 0.3982 0.077 Uiso 1 1 calc R . .
C19 C 0.4648(7) 0.3250(4) 0.3397(3) 0.0639(14) Uani 1 1 d . . .
H19 H 0.5450 0.2953 0.3757 0.077 Uiso 1 1 calc R . .
C20 C 0.3875(6) 0.2771(3) 0.2726(3) 0.0537(12) Uani 1 1 d . . .
H20 H 0.4170 0.2150 0.2639 0.064 Uiso 1 1 calc R . .
N4 N 0.2714(4) 0.3174(2) 0.2198(2) 0.0436(8) 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
Cu1 N1 1.999(3) . ?
Cu1 N4 2.017(3) . ?
Cu1 N2 2.064(3) . ?
Cu1 Cl2 2.3024(15) . ?
Cu1 Cl1 2.5245(18) . ?
N1 C1 1.343(6) . ?
N1 C5 1.346(5) . ?
C1 C2 1.371(7) . ?
C1 H1 0.9300 . ?
C2 C3 1.362(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.388(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.497(6) . ?
C6 N2 1.462(5) . ?
C6 H07A 0.9700 . ?
C6 H07B 0.9700 . ?
N2 C7 1.300(5) . ?
C7 N3 1.359(5) . ?
C7 C8 1.482(5) . ?
C8 C13 1.379(7) . ?
C8 C9 1.399(7) . ?
C9 C10 1.394(7) . ?
C9 H9 0.9300 . ?
C10 C11 1.390(9) . ?
C10 H10 0.9300 . ?
C11 C12 1.362(9) . ?
C11 H11 0.9300 . ?
C12 C13 1.384(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.489(7) . ?
C14 N3 1.453(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
N3 C15 1.452(5) . ?
C15 C16 1.491(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 N4 1.350(6) . ?
C16 C17 1.392(6) . ?
C17 C18 1.384(8) . ?
C17 H17 0.9300 . ?
C18 C19 1.381(8) . ?
C18 H18 0.9300 . ?
C19 C20 1.380(7) . ?
C19 H19 0.9300 . ?
C20 N4 1.336(6) . ?
C20 H20 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Cu1 N4 173.37(15) . . ?
N1 Cu1 N2 79.68(14) . . ?
N4 Cu1 N2 96.42(13) . . ?
N1 Cu1 Cl2 93.85(11) . . ?
N4 Cu1 Cl2 87.30(11) . . ?
N2 Cu1 Cl2 153.67(12) . . ?
N1 Cu1 Cl1 92.24(12) . . ?
N4 Cu1 Cl1 93.50(12) . . ?
N2 Cu1 Cl1 95.74(11) . . ?
Cl2 Cu1 Cl1 110.08(7) . . ?
C1 N1 C5 118.2(4) . . ?
C1 N1 Cu1 127.9(3) . . ?
C5 N1 Cu1 113.7(3) . . ?
N1 C1 C2 123.3(5) . . ?
N1 C1 H1 118.4 . . ?
C2 C1 H1 118.4 . . ?
C3 C2 C1 118.4(5) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C2 C3 C4 119.7(4) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 119.0(5) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
N1 C5 C4 121.4(4) . . ?
N1 C5 C6 115.5(3) . . ?
C4 C5 C6 123.1(4) . . ?
N2 C6 C5 108.5(3) . . ?
N2 C6 H07A 110.0 . . ?
C5 C6 H07A 110.0 . . ?
N2 C6 H07B 110.0 . . ?
C5 C6 H07B 110.0 . . ?
H07A C6 H07B 108.4 . . ?
C7 N2 C6 119.7(3) . . ?
C7 N2 Cu1 133.3(3) . . ?
C6 N2 Cu1 106.0(2) . . ?
N2 C7 N3 121.1(4) . . ?
N2 C7 C8 133.2(4) . . ?
N3 C7 C8 105.7(4) . . ?
C13 C8 C9 119.9(4) . . ?
C13 C8 C7 108.4(4) . . ?
C9 C8 C7 131.6(4) . . ?
C10 C9 C8 117.6(5) . . ?
C10 C9 H9 121.2 . . ?
C8 C9 H9 121.2 . . ?
C11 C10 C9 121.0(6) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C12 C11 C10 121.4(5) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C11 C12 C13 117.8(6) . . ?
C11 C12 H12 121.1 . . ?
C13 C12 H12 121.1 . . ?
C8 C13 C12 122.3(5) . . ?
C8 C13 C14 110.0(4) . . ?
C12 C13 C14 127.6(5) . . ?
N3 C14 C13 101.9(4) . . ?
N3 C14 H14A 111.4 . . ?
C13 C14 H14A 111.4 . . ?
N3 C14 H14B 111.4 . . ?
C13 C14 H14B 111.4 . . ?
H14A C14 H14B 109.3 . . ?
C7 N3 C15 124.5(3) . . ?
C7 N3 C14 113.9(4) . . ?
C15 N3 C14 121.6(4) . . ?
N3 C15 C16 111.5(3) . . ?
N3 C15 H15A 109.3 . . ?
C16 C15 H15A 109.3 . . ?
N3 C15 H15B 109.3 . . ?
C16 C15 H15B 109.3 . . ?
H15A C15 H15B 108.0 . . ?
N4 C16 C17 121.6(4) . . ?
N4 C16 C15 117.2(3) . . ?
C17 C16 C15 121.2(4) . . ?
C18 C17 C16 118.8(5) . . ?
C18 C17 H17 120.6 . . ?
C16 C17 H17 120.6 . . ?
C19 C18 C17 118.9(5) . . ?
C19 C18 H18 120.5 . . ?
C17 C18 H18 120.5 . . ?
C20 C19 C18 119.6(5) . . ?
C20 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
N4 C20 C19 121.8(5) . . ?
N4 C20 H20 119.1 . . ?
C19 C20 H20 119.1 . . ?
C20 N4 C16 119.2(4) . . ?
C20 N4 Cu1 119.5(3) . . ?
C16 N4 Cu1 120.9(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N4 Cu1 N1 C1 -107.6(12) . . . . ?
N2 Cu1 N1 C1 -162.1(4) . . . . ?
Cl2 Cu1 N1 C1 -7.9(4) . . . . ?
Cl1 Cu1 N1 C1 102.4(4) . . . . ?
N4 Cu1 N1 C5 78.2(13) . . . . ?
N2 Cu1 N1 C5 23.7(3) . . . . ?
Cl2 Cu1 N1 C5 178.0(3) . . . . ?
Cl1 Cu1 N1 C5 -71.7(3) . . . . ?
C5 N1 C1 C2 1.9(7) . . . . ?
Cu1 N1 C1 C2 -172.0(4) . . . . ?
N1 C1 C2 C3 -0.8(8) . . . . ?
C1 C2 C3 C4 -0.8(8) . . . . ?
C2 C3 C4 C5 1.1(8) . . . . ?
C1 N1 C5 C4 -1.5(6) . . . . ?
Cu1 N1 C5 C4 173.2(3) . . . . ?
C1 N1 C5 C6 178.9(4) . . . . ?
Cu1 N1 C5 C6 -6.4(5) . . . . ?
C3 C4 C5 N1 0.1(7) . . . . ?
C3 C4 C5 C6 179.6(4) . . . . ?
N1 C5 C6 N2 -24.0(5) . . . . ?
C4 C5 C6 N2 156.4(4) . . . . ?
C5 C6 N2 C7 -148.7(4) . . . . ?
C5 C6 N2 Cu1 40.7(4) . . . . ?
N1 Cu1 N2 C7 155.8(4) . . . . ?
N4 Cu1 N2 C7 -18.8(4) . . . . ?
Cl2 Cu1 N2 C7 78.2(5) . . . . ?
Cl1 Cu1 N2 C7 -112.9(4) . . . . ?
N1 Cu1 N2 C6 -35.4(3) . . . . ?
N4 Cu1 N2 C6 150.0(3) . . . . ?
Cl2 Cu1 N2 C6 -113.0(3) . . . . ?
Cl1 Cu1 N2 C6 55.9(3) . . . . ?
C6 N2 C7 N3 169.1(4) . . . . ?
Cu1 N2 C7 N3 -23.3(6) . . . . ?
C6 N2 C7 C8 -10.3(7) . . . . ?
Cu1 N2 C7 C8 157.2(3) . . . . ?
N2 C7 C8 C13 -178.7(4) . . . . ?
N3 C7 C8 C13 1.9(4) . . . . ?
N2 C7 C8 C9 -1.7(8) . . . . ?
N3 C7 C8 C9 178.8(4) . . . . ?
C13 C8 C9 C10 -2.9(7) . . . . ?
C7 C8 C9 C10 -179.5(4) . . . . ?
C8 C9 C10 C11 2.0(8) . . . . ?
C9 C10 C11 C12 -0.2(9) . . . . ?
C10 C11 C12 C13 -0.7(9) . . . . ?
C9 C8 C13 C12 2.0(7) . . . . ?
C7 C8 C13 C12 179.4(4) . . . . ?
C9 C8 C13 C14 -176.5(4) . . . . ?
C7 C8 C13 C14 0.9(5) . . . . ?
C11 C12 C13 C8 -0.2(8) . . . . ?
C11 C12 C13 C14 178.0(5) . . . . ?
C8 C13 C14 N3 -3.0(5) . . . . ?
C12 C13 C14 N3 178.6(5) . . . . ?
N2 C7 N3 C15 -2.8(6) . . . . ?
C8 C7 N3 C15 176.7(4) . . . . ?
N2 C7 N3 C14 176.4(4) . . . . ?
C8 C7 N3 C14 -4.0(5) . . . . ?
C13 C14 N3 C7 4.4(5) . . . . ?
C13 C14 N3 C15 -176.3(4) . . . . ?
C7 N3 C15 C16 83.4(5) . . . . ?
C14 N3 C15 C16 -95.8(5) . . . . ?
N3 C15 C16 N4 -79.4(5) . . . . ?
N3 C15 C16 C17 97.7(5) . . . . ?
N4 C16 C17 C18 -2.0(7) . . . . ?
C15 C16 C17 C18 -179.0(4) . . . . ?
C16 C17 C18 C19 1.7(7) . . . . ?
C17 C18 C19 C20 -0.6(8) . . . . ?
C18 C19 C20 N4 -0.2(8) . . . . ?
C19 C20 N4 C16 -0.1(7) . . . . ?
C19 C20 N4 Cu1 -173.4(4) . . . . ?
C17 C16 N4 C20 1.2(6) . . . . ?
C15 C16 N4 C20 178.3(4) . . . . ?
C17 C16 N4 Cu1 174.4(3) . . . . ?
C15 C16 N4 Cu1 -8.5(5) . . . . ?
N1 Cu1 N4 C20 172.4(11) . . . . ?
N2 Cu1 N4 C20 -133.9(3) . . . . ?
Cl2 Cu1 N4 C20 72.3(3) . . . . ?
Cl1 Cu1 N4 C20 -37.7(3) . . . . ?
N1 Cu1 N4 C16 -0.7(14) . . . . ?
N2 Cu1 N4 C16 53.0(3) . . . . ?
Cl2 Cu1 N4 C16 -100.9(3) . . . . ?
Cl1 Cu1 N4 C16 149.1(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.34
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.693
_refine_diff_density_min         -0.695
_refine_diff_density_rms         0.083

#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_2
_database_code_depnum_ccdc_archive 'CCDC 974888'
_audit_update_record             
;
2015-02-13 deposited with the CCDC.
2015-02-27 downloaded from the CCDC.
;

#------------------ AUDIT DETAILS -------------------------------------------#

_audit_creation_date             2013-05-20
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#------------------  SECTION 2. COMPOUND(S) DETAILS -------------------------#


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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C20 H18 Cl2 Co1 N4'
_chemical_formula_sum            'C20 H18 Cl2 Co N4'
_chemical_formula_weight         444.21
_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                   8.733(5)
_cell_length_b                   12.221(5)
_cell_length_c                   13.101(5)
_cell_angle_alpha                64.207(5)
_cell_angle_beta                 74.485(5)
_cell_angle_gamma                85.967(5)
_cell_volume                     1211.3(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.07
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             454

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

_exptl_absorpt_coefficient_mu    7.658
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
        (compiled Dec  3 2012,18:21:49)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.22275
_exptl_absorpt_correction_T_max  1

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

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector_area_resol_mean 10.3756
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_number            4227
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.88
_diffrn_reflns_theta_max         66.56
_diffrn_reflns_theta_full        66.56
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_reflns_number_total             4227
_reflns_number_gt                3266
_reflns_threshold_expression     >2sigma(I)

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

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

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

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

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

_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)+(0.0576P)²+0.0351P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4227
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.043
_refine_ls_wR_factor_ref         0.1163
_refine_ls_wR_factor_gt          0.1094
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.041

# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.020 0.000 0.000 329 9 ' '
_platon_squeeze_details          
;
;

#----------------------------------------------------------------------------#
#                   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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co -2.3653 3.6143 '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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.73896(5) 0.44452(4) 0.26349(4) 0.05973(17) Uani 1 1 d . . .
Cl1 Cl 0.98856(9) 0.36932(8) 0.27486(8) 0.0803(3) Uani 1 1 d . . .
Cl2 Cl 0.70362(13) 0.64249(7) 0.13658(10) 0.1083(4) Uani 1 1 d . . .
N3 N 0.4093(3) 0.2677(2) 0.3248(2) 0.0597(6) Uani 1 1 d . . .
N2 N 0.5699(3) 0.3268(2) 0.4089(2) 0.0591(6) Uani 1 1 d . . .
N4 N 0.7236(3) 0.3799(2) 0.1372(2) 0.0616(6) Uani 1 1 d . . .
C7 C 0.4657(3) 0.2505(2) 0.4164(3) 0.0575(7) Uani 1 1 d . . .
C13 C 0.2922(3) 0.0866(3) 0.4721(3) 0.0688(8) Uani 1 1 d . . .
N1 N 0.7475(3) 0.5034(3) 0.3943(3) 0.0755(7) Uani 1 1 d . . .
C14 C 0.3038(3) 0.1677(3) 0.3474(3) 0.0702(8) Uani 1 1 d . . .
H14A H 0.3494 0.1275 0.2975 0.084 Uiso 1 1 calc R . .
H14B H 0.2004 0.1958 0.3357 0.084 Uiso 1 1 calc R . .
C8 C 0.3864(3) 0.1341(3) 0.5153(3) 0.0626(7) Uani 1 1 d . . .
C16 C 0.5789(4) 0.3649(2) 0.1250(3) 0.0625(7) Uani 1 1 d . . .
C9 C 0.3950(4) 0.0709(3) 0.6306(3) 0.0820(9) Uani 1 1 d . . .
H9 H 0.4588 0.1008 0.6604 0.098 Uiso 1 1 calc R . .
C15 C 0.4378(3) 0.3764(3) 0.2137(3) 0.0650(8) Uani 1 1 d . . .
H15A H 0.4559 0.4465 0.2263 0.078 Uiso 1 1 calc R . .
H15B H 0.3444 0.3895 0.1838 0.078 Uiso 1 1 calc R . .
C6 C 0.6015(4) 0.3109(3) 0.5191(3) 0.0740(8) Uani 1 1 d . . .
H6A H 0.6644 0.2405 0.5461 0.089 Uiso 1 1 calc R . .
H6B H 0.5015 0.2961 0.5788 0.089 Uiso 1 1 calc R . .
C12 C 0.2059(4) -0.0242(3) 0.5434(4) 0.0842(10) Uani 1 1 d . . .
H12 H 0.1445 -0.0564 0.5139 0.101 Uiso 1 1 calc R . .
C5 C 0.6880(4) 0.4201(3) 0.5034(3) 0.0722(8) Uani 1 1 d . . .
C19 C 0.8420(5) 0.3366(3) -0.0260(3) 0.0870(11) Uani 1 1 d . . .
H19 H 0.9339 0.3274 -0.0766 0.104 Uiso 1 1 calc R . .
C20 C 0.8514(4) 0.3657(3) 0.0628(3) 0.0730(9) Uani 1 1 d . . .
H20 H 0.9513 0.3758 0.0709 0.088 Uiso 1 1 calc R . .
C17 C 0.5623(5) 0.3364(3) 0.0372(3) 0.0781(9) Uani 1 1 d . . .
H17 H 0.4617 0.3275 0.0294 0.094 Uiso 1 1 calc R . .
C4 C 0.7092(4) 0.4318(4) 0.5989(4) 0.0936(12) Uani 1 1 d . . .
H4 H 0.6656 0.3731 0.6749 0.112 Uiso 1 1 calc R . .
C3 C 0.7954(5) 0.5312(5) 0.5798(5) 0.1107(16) Uani 1 1 d . . .
H3 H 0.8134 0.5394 0.643 0.133 Uiso 1 1 calc R . .
C10 C 0.3056(5) -0.0385(3) 0.7005(3) 0.0936(11) Uani 1 1 d . . .
H10 H 0.3089 -0.0814 0.7784 0.112 Uiso 1 1 calc R . .
C1 C 0.8286(4) 0.6035(4) 0.3754(4) 0.0941(12) Uani 1 1 d . . .
H1 H 0.8674 0.6631 0.2991 0.113 Uiso 1 1 calc R . .
C2 C 0.8548(5) 0.6184(5) 0.4683(6) 0.1098(16) Uani 1 1 d . . .
H2 H 0.9122 0.6868 0.4548 0.132 Uiso 1 1 calc R . .
C18 C 0.6954(6) 0.3216(3) -0.0384(3) 0.0931(12) Uani 1 1 d . . .
H18 H 0.6862 0.3016 -0.0974 0.112 Uiso 1 1 calc R . .
C11 C 0.2132(5) -0.0846(3) 0.6576(4) 0.0962(12) Uani 1 1 d . . .
H11 H 0.1545 -0.1579 0.7066 0.115 Uiso 1 1 calc R . .



#----------------------------------------------------------------------------#
#                   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
Co1 N2 2.071(2) . ?
Co1 N1 2.147(3) . ?
Co1 N4 2.157(3) . ?
Co1 Cl2 2.3199(12) . ?
Co1 Cl1 2.3218(15) . ?
N3 C7 1.344(4) . ?
N3 C15 1.454(4) . ?
N3 C14 1.459(4) . ?
N2 C7 1.304(3) . ?
N2 C6 1.469(4) . ?
N4 C20 1.327(4) . ?
N4 C16 1.350(4) . ?
C7 C8 1.495(4) . ?
C13 C8 1.392(4) . ?
C13 C12 1.393(4) . ?
C13 C14 1.475(5) . ?
N1 C5 1.327(4) . ?
N1 C1 1.350(4) . ?
C14 H14A 0.97 . ?
C14 H14B 0.97 . ?
C8 C9 1.385(4) . ?
C16 C17 1.382(4) . ?
C16 C15 1.497(4) . ?
C9 C10 1.391(5) . ?
C9 H9 0.93 . ?
C15 H15A 0.97 . ?
C15 H15B 0.97 . ?
C6 C5 1.487(5) . ?
C6 H6A 0.97 . ?
C6 H6B 0.97 . ?
C12 C11 1.368(5) . ?
C12 H12 0.93 . ?
C5 C4 1.380(5) . ?
C19 C18 1.367(5) . ?
C19 C20 1.379(5) . ?
C19 H19 0.93 . ?
C20 H20 0.93 . ?
C17 C18 1.369(5) . ?
C17 H17 0.93 . ?
C4 C3 1.368(6) . ?
C4 H4 0.93 . ?
C3 C2 1.362(7) . ?
C3 H3 0.93 . ?
C10 C11 1.367(6) . ?
C10 H10 0.93 . ?
C1 C2 1.383(6) . ?
C1 H1 0.93 . ?
C2 H2 0.93 . ?
C18 H18 0.93 . ?
C11 H11 0.93 . ?

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 Co1 N1 78.01(10) . . ?
N2 Co1 N4 99.77(9) . . ?
N1 Co1 N4 177.78(10) . . ?
N2 Co1 Cl2 126.64(8) . . ?
N1 Co1 Cl2 90.28(9) . . ?
N4 Co1 Cl2 91.13(7) . . ?
N2 Co1 Cl1 108.68(7) . . ?
N1 Co1 Cl1 87.41(8) . . ?
N4 Co1 Cl1 93.26(7) . . ?
Cl2 Co1 Cl1 122.74(4) . . ?
C7 N3 C15 125.9(2) . . ?
C7 N3 C14 113.8(2) . . ?
C15 N3 C14 120.2(2) . . ?
C7 N2 C6 117.1(2) . . ?
C7 N2 Co1 129.6(2) . . ?
C6 N2 Co1 111.62(19) . . ?
C20 N4 C16 118.3(3) . . ?
C20 N4 Co1 122.5(2) . . ?
C16 N4 Co1 118.8(2) . . ?
N2 C7 N3 122.0(2) . . ?
N2 C7 C8 131.8(3) . . ?
N3 C7 C8 106.3(2) . . ?
C8 C13 C12 120.8(3) . . ?
C8 C13 C14 110.5(3) . . ?
C12 C13 C14 128.7(3) . . ?
C5 N1 C1 119.7(3) . . ?
C5 N1 Co1 113.2(2) . . ?
C1 N1 Co1 126.1(3) . . ?
N3 C14 C13 102.2(2) . . ?
N3 C14 H14A 111.3 . . ?
C13 C14 H14A 111.3 . . ?
N3 C14 H14B 111.3 . . ?
C13 C14 H14B 111.3 . . ?
H14A C14 H14B 109.2 . . ?
C9 C8 C13 119.9(3) . . ?
C9 C8 C7 132.9(3) . . ?
C13 C8 C7 107.1(3) . . ?
N4 C16 C17 121.5(3) . . ?
N4 C16 C15 116.7(3) . . ?
C17 C16 C15 121.8(3) . . ?
C8 C9 C10 118.2(4) . . ?
C8 C9 H9 120.9 . . ?
C10 C9 H9 120.9 . . ?
N3 C15 C16 111.1(2) . . ?
N3 C15 H15A 109.4 . . ?
C16 C15 H15A 109.4 . . ?
N3 C15 H15B 109.4 . . ?
C16 C15 H15B 109.4 . . ?
H15A C15 H15B 108 . . ?
N2 C6 C5 111.5(3) . . ?
N2 C6 H6A 109.3 . . ?
C5 C6 H6A 109.3 . . ?
N2 C6 H6B 109.3 . . ?
C5 C6 H6B 109.3 . . ?
H6A C6 H6B 108 . . ?
C11 C12 C13 118.7(4) . . ?
C11 C12 H12 120.7 . . ?
C13 C12 H12 120.7 . . ?
N1 C5 C4 121.6(3) . . ?
N1 C5 C6 117.5(3) . . ?
C4 C5 C6 120.9(4) . . ?
C18 C19 C20 118.9(4) . . ?
C18 C19 H19 120.5 . . ?
C20 C19 H19 120.5 . . ?
N4 C20 C19 122.7(3) . . ?
N4 C20 H20 118.6 . . ?
C19 C20 H20 118.6 . . ?
C18 C17 C16 119.4(3) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
C3 C4 C5 118.8(4) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
C2 C3 C4 120.1(4) . . ?
C2 C3 H3 120 . . ?
C4 C3 H3 120 . . ?
C11 C10 C9 121.6(4) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
N1 C1 C2 120.8(4) . . ?
N1 C1 H1 119.6 . . ?
C2 C1 H1 119.6 . . ?
C3 C2 C1 119.0(4) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C19 C18 C17 119.2(3) . . ?
C19 C18 H18 120.4 . . ?
C17 C18 H18 120.4 . . ?
C10 C11 C12 120.8(4) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?

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 Co1 N2 C7 169.6(2) . . . . ?
N4 Co1 N2 C7 -10.5(2) . . . . ?
Cl2 Co1 N2 C7 88.3(2) . . . . ?
Cl1 Co1 N2 C7 -107.3(2) . . . . ?
N1 Co1 N2 C6 -25.54(19) . . . . ?
N4 Co1 N2 C6 154.38(19) . . . . ?
Cl2 Co1 N2 C6 -106.81(19) . . . . ?
Cl1 Co1 N2 C6 57.5(2) . . . . ?
N2 Co1 N4 C20 -137.3(2) . . . . ?
N1 Co1 N4 C20 -135(2) . . . . ?
Cl2 Co1 N4 C20 95.2(2) . . . . ?
Cl1 Co1 N4 C20 -27.7(2) . . . . ?
N2 Co1 N4 C16 49.5(2) . . . . ?
N1 Co1 N4 C16 52(3) . . . . ?
Cl2 Co1 N4 C16 -78.0(2) . . . . ?
Cl1 Co1 N4 C16 159.11(19) . . . . ?
C6 N2 C7 N3 169.3(3) . . . . ?
Co1 N2 C7 N3 -26.5(4) . . . . ?
C6 N2 C7 C8 -11.2(4) . . . . ?
Co1 N2 C7 C8 153.0(2) . . . . ?
C15 N3 C7 N2 -8.3(4) . . . . ?
C14 N3 C7 N2 175.3(2) . . . . ?
C15 N3 C7 C8 172.1(2) . . . . ?
C14 N3 C7 C8 -4.3(3) . . . . ?
N2 Co1 N1 C5 20.0(2) . . . . ?
N4 Co1 N1 C5 18(3) . . . . ?
Cl2 Co1 N1 C5 147.5(2) . . . . ?
Cl1 Co1 N1 C5 -89.7(2) . . . . ?
N2 Co1 N1 C1 -171.8(3) . . . . ?
N4 Co1 N1 C1 -174(2) . . . . ?
Cl2 Co1 N1 C1 -44.3(3) . . . . ?
Cl1 Co1 N1 C1 78.5(3) . . . . ?
C7 N3 C14 C13 3.9(3) . . . . ?
C15 N3 C14 C13 -172.8(2) . . . . ?
C8 C13 C14 N3 -1.7(3) . . . . ?
C12 C13 C14 N3 179.5(3) . . . . ?
C12 C13 C8 C9 0.0(4) . . . . ?
C14 C13 C8 C9 -178.9(3) . . . . ?
C12 C13 C8 C7 178.3(3) . . . . ?
C14 C13 C8 C7 -0.6(3) . . . . ?
N2 C7 C8 C9 1.4(5) . . . . ?
N3 C7 C8 C9 -179.1(3) . . . . ?
N2 C7 C8 C13 -176.6(3) . . . . ?
N3 C7 C8 C13 3.0(3) . . . . ?
C20 N4 C16 C17 -0.5(4) . . . . ?
Co1 N4 C16 C17 172.9(2) . . . . ?
C20 N4 C16 C15 177.5(2) . . . . ?
Co1 N4 C16 C15 -9.1(3) . . . . ?
C13 C8 C9 C10 -1.1(5) . . . . ?
C7 C8 C9 C10 -178.8(3) . . . . ?
C7 N3 C15 C16 93.0(3) . . . . ?
C14 N3 C15 C16 -90.8(3) . . . . ?
N4 C16 C15 N3 -76.7(3) . . . . ?
C17 C16 C15 N3 101.3(3) . . . . ?
C7 N2 C6 C5 -165.2(2) . . . . ?
Co1 N2 C6 C5 27.9(3) . . . . ?
C8 C13 C12 C11 1.1(5) . . . . ?
C14 C13 C12 C11 179.8(3) . . . . ?
C1 N1 C5 C4 -1.1(5) . . . . ?
Co1 N1 C5 C4 167.9(2) . . . . ?
C1 N1 C5 C6 -179.2(3) . . . . ?
Co1 N1 C5 C6 -10.2(4) . . . . ?
N2 C6 C5 N1 -11.4(4) . . . . ?
N2 C6 C5 C4 170.5(3) . . . . ?
C16 N4 C20 C19 0.1(4) . . . . ?
Co1 N4 C20 C19 -173.1(2) . . . . ?
C18 C19 C20 N4 0.0(5) . . . . ?
N4 C16 C17 C18 0.8(4) . . . . ?
C15 C16 C17 C18 -177.1(3) . . . . ?
N1 C5 C4 C3 -0.8(5) . . . . ?
C6 C5 C4 C3 177.2(3) . . . . ?
C5 C4 C3 C2 1.9(6) . . . . ?
C8 C9 C10 C11 1.0(5) . . . . ?
C5 N1 C1 C2 2.0(5) . . . . ?
Co1 N1 C1 C2 -165.5(3) . . . . ?
C4 C3 C2 C1 -1.0(6) . . . . ?
N1 C1 C2 C3 -1.0(6) . . . . ?
C20 C19 C18 C17 0.3(5) . . . . ?
C16 C17 C18 C19 -0.7(5) . . . . ?
C9 C10 C11 C12 0.2(6) . . . . ?
C13 C12 C11 C10 -1.2(5) . . . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+:"~<>?|\-=[];'`,./

# 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_3
_database_code_depnum_ccdc_archive 'CCDC 980973'
_audit_update_record             
;
2015-02-13 deposited with the CCDC.
2015-02-27 downloaded from the CCDC.
;

#------------------ AUDIT DETAILS -------------------------------------------#

_audit_creation_date             2013-12-17
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#------------------  SECTION 2. COMPOUND(S) DETAILS -------------------------#



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

_chemical_name_systematic        
;
 ?
;
_chemical_name_common            'Compound 3'
_chemical_formula_sum            'C28 H39 Cu N4 O13'
_chemical_formula_moiety         'C28 H39 Cu N4 O13'
_chemical_formula_weight         703.17

#----------------------------------------------------------------------------#
#                   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                   11.6680(2)
_cell_length_b                   11.9800(2)
_cell_length_c                   13.5510(2)
_cell_angle_alpha                110.9190(10)
_cell_angle_beta                 107.1370(10)
_cell_angle_gamma                100.5860(10)
_cell_volume                     1599.77(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    20895
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      27.485

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

_exptl_crystal_description       prism
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.14
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_F_000             738
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-7 1 3 0.177
7 -1 -3 0.202
-1 -4 11 0.164
-1 6 -15 0.121
1 2 -4 0.09
-1 -2 3 0.135

_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.754
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   '(DENZO-SMN; Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min  0.778
_exptl_absorpt_correction_T_max  0.902


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

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_detector_area_resol_mean 9
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_ub_11      0.0863039
_diffrn_orient_matrix_ub_12      0.0151752
_diffrn_orient_matrix_ub_13      0.0553545
_diffrn_orient_matrix_ub_21      -0.0183766
_diffrn_orient_matrix_ub_22      0.0551554
_diffrn_orient_matrix_ub_23      0.0646799
_diffrn_orient_matrix_ub_31      -0.0346164
_diffrn_orient_matrix_ub_32      -0.0751559
_diffrn_orient_matrix_ub_33      0.0113946
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_number            25793
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.791
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.987
_reflns_number_total             7264
_reflns_number_gt                6756
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_computing_molecular_graphics    'Ortep (Johnson, 1976)'

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

_atom_sites_solution_hydrogens   mixed

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

_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 > 2σ(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.
 All hydrogen atoms joined to carbon atoms were positioned with an idealized 
 geometry and refined using a riding model with Uiso(H) fixed at 1.2 Ueq of C. 
 Hydrogen atoms of water molecule were found from the difference Fourier and 
 refined with restrained bond lengths and angles. Uiso(H) were constrained to 
 1.5 Ueq of their home O atom.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0340P)²+1.2899P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         7264
_refine_ls_number_parameters     469
_refine_ls_number_restraints     27
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.03
_refine_ls_wR_factor_ref         0.0789
_refine_ls_wR_factor_gt          0.0764
_refine_ls_goodness_of_fit_gt    5.621
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.547
_refine_diff_density_min         -0.46
_refine_diff_density_rms         0.058

#----------------------------------------------------------------------------#
#                   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'
Cu Cu 0.3201 1.2651 '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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.48258(2) 0.34954(2) 0.24614(2) 0.01035(6) Uani 1 d . .
N4 N 0.56987(11) 0.22811(11) 0.18062(10) 0.0115(2) Uani 1 d . .
C20 C 0.57273(13) 0.20664(14) 0.07694(13) 0.0137(3) Uani 1 d . .
H20 H 0.5361 0.2515 0.038 0.016 Uiso 1 calc . .
C19 C 0.62701(14) 0.12166(14) 0.02476(13) 0.0158(3) Uani 1 d . .
H19 H 0.6297 0.11 -0.0475 0.019 Uiso 1 calc . .
C18 C 0.67728(14) 0.05411(14) 0.08061(13) 0.0170(3) Uani 1 d . .
H18 H 0.7135 -0.006 0.0462 0.02 Uiso 1 calc . .
C17 C 0.67426(14) 0.07494(14) 0.18728(13) 0.0153(3) Uani 1 d . .
H17 H 0.7083 0.0295 0.2268 0.018 Uiso 1 calc . .
C16 C 0.62055(13) 0.16351(13) 0.23518(12) 0.0123(3) Uani 1 d . .
C15 C 0.62242(14) 0.19950(13) 0.35407(12) 0.0133(3) Uani 1 d . .
H15A H 0.5406 0.2108 0.3547 0.016 Uiso 1 calc . .
H15B H 0.6337 0.1312 0.3769 0.016 Uiso 1 calc . .
N3 N 0.72546(11) 0.31623(11) 0.43533(10) 0.0124(2) Uani 1 d . .
C14 C 0.84916(14) 0.31363(14) 0.49857(13) 0.0144(3) Uani 1 d . .
H14A H 0.8917 0.2798 0.4467 0.017 Uiso 1 calc . .
H14B H 0.8421 0.2627 0.5415 0.017 Uiso 1 calc . .
C13 C 0.91753(14) 0.45026(14) 0.57800(12) 0.0133(3) Uani 1 d . .
C12 C 1.03940(14) 0.50481(15) 0.66253(13) 0.0161(3) Uani 1 d . .
H12 H 1.092 0.455 0.674 0.019 Uiso 1 calc . .
C11 C 1.08211(14) 0.63429(16) 0.72983(14) 0.0187(3) Uani 1 d . .
H11 H 1.1644 0.6735 0.7896 0.022 Uiso 1 calc . .
C10 C 1.00589(15) 0.70758(15) 0.71089(14) 0.0195(3) Uani 1 d . .
H10 H 1.0371 0.7961 0.7581 0.023 Uiso 1 calc . .
C9 C 0.88479(14) 0.65358(14) 0.62398(13) 0.0160(3) Uani 1 d . .
H9 H 0.834 0.7043 0.6102 0.019 Uiso 1 calc . .
C8 C 0.84006(13) 0.52258(14) 0.55748(12) 0.0121(3) Uani 1 d . .
C7 C 0.71793(13) 0.43435(13) 0.46080(12) 0.0113(3) Uani 1 d . .
N2 N 0.61831(11) 0.45523(11) 0.40526(10) 0.0114(2) Uani 1 d . .
C6 C 0.61453(13) 0.58493(13) 0.44981(12) 0.0128(3) Uani 1 d . .
H6A H 0.6813 0.6399 0.4408 0.015 Uiso 1 calc . .
H6B H 0.6318 0.617 0.5327 0.015 Uiso 1 calc . .
C5 C 0.48705(13) 0.58983(14) 0.38672(12) 0.0120(3) Uani 1 d . .
C4 C 0.46006(15) 0.70275(14) 0.41664(13) 0.0155(3) Uani 1 d . .
H4 H 0.5217 0.7785 0.4782 0.019 Uiso 1 calc . .
C3 C 0.34209(15) 0.70321(15) 0.35536(14) 0.0174(3) Uani 1 d . .
H3 H 0.3219 0.7794 0.3742 0.021 Uiso 1 calc . .
C2 C 0.25364(15) 0.59107(16) 0.26605(14) 0.0177(3) Uani 1 d . .
H2 H 0.1715 0.5889 0.2239 0.021 Uiso 1 calc . .
C1 C 0.28751(14) 0.48266(15) 0.23983(13) 0.0154(3) Uani 1 d . .
H1 H 0.2278 0.4061 0.1779 0.018 Uiso 1 calc . .
N1 N 0.40239(11) 0.48189(12) 0.29908(11) 0.0122(2) Uani 1 d . .
O2 O 0.31708(10) 0.23216(10) 0.11772(9) 0.0141(2) Uani 1 d . .
C21 C 0.25709(13) 0.16672(13) 0.15528(13) 0.0130(3) Uani 1 d . .
O3 O 0.30316(10) 0.17310(10) 0.25311(9) 0.0175(2) Uani 1 d . .
C22 C 0.12402(13) 0.08056(13) 0.07413(13) 0.0129(3) Uani 1 d . .
C24 C 0.06984(14) 0.07254(14) -0.03589(13) 0.0152(3) Uani 1 d . .
H24 H 0.1172 0.1221 -0.0607 0.018 Uiso 1 calc . .
C23 C 0.05274(14) 0.00737(15) 0.10933(13) 0.0160(3) Uani 1 d . .
H23 H 0.0884 0.0123 0.1841 0.019 Uiso 1 calc . .
O4 O 0.73574(11) 0.46740(11) 0.09097(10) 0.0194(2) Uani 1 d . .
C25 C 0.82920(14) 0.55744(15) 0.11476(13) 0.0153(3) Uani 1 d . .
O5 O 0.85496(11) 0.67098(11) 0.18512(10) 0.0190(2) Uani 1 d . .
C26 C 0.91793(14) 0.52806(14) 0.05504(13) 0.0135(3) Uani 1 d . .
C27 C 0.92074(14) 0.40487(15) 0.00857(13) 0.0156(3) Uani 1 d . .
H27 H 0.8668 0.34 0.0145 0.019 Uiso 1 calc . .
C28 C 0.99770(14) 0.62336(15) 0.04652(13) 0.0154(3) Uani 1 d . .
H28 H 0.9962 0.7075 0.0784 0.019 Uiso 1 calc . .
O1 O 0.54596(12) 0.47028(11) 0.16471(11) 0.0218(2) Uani 1 d . .
O6 O 0.82579(13) 0.76659(12) 0.39826(11) 0.0268(3) Uani 1 d . .
O7 O 0.45951(11) 0.66211(11) 0.12582(10) 0.0204(2) Uani 1 d . .
O8 O 0.47285(13) 0.90253(12) 0.26896(12) 0.0281(3) Uani 1 d . .
O9 O 0.29871(12) 0.99724(12) 0.34523(11) 0.0249(3) Uani 1 d . .
O10 O 0.05963(16) 0.88592(15) 0.32053(16) 0.0483(4) Uani 1 d . .
O11 O 0.29171(14) 1.04663(14) 0.57167(12) 0.0330(3) Uani 1 d . .
O12 O 0.32469(11) 1.22934(11) 0.89964(10) 0.0204(2) Uani 1 d . .
O13 O 0.95110(14) 1.06814(13) 0.40979(13) 0.0337(3) Uani 1 d . .
H1A H 0.617(2) 0.483(3) 0.148(2) 0.051 Uiso 1 d . .
H1B H 0.513(2) 0.532(2) 0.158(2) 0.051 Uiso 1 d . .
H6C H 0.826(3) 0.730(2) 0.3269(16) 0.051 Uiso 1 d . .
H6D H 0.781(2) 0.824(2) 0.399(2) 0.051 Uiso 1 d . .
H7C H 0.5307(19) 0.691(2) 0.115(2) 0.051 Uiso 1 d . .
H7D H 0.3901(19) 0.619(2) 0.0583(18) 0.051 Uiso 1 d . .
H8C H 0.450(2) 0.8177(17) 0.220(2) 0.051 Uiso 1 d . .
H8D H 0.5502(19) 0.918(2) 0.3268(19) 0.051 Uiso 1 d . .
H9C H 0.292(3) 1.056(2) 0.314(2) 0.051 Uiso 1 d . .
H9D H 0.343(2) 0.955(2) 0.302(2) 0.051 Uiso 1 d . .
H10C H 0.001(2) 0.8085(19) 0.272(2) 0.051 Uiso 1 d . .
H10D H 0.1393(17) 0.895(3) 0.327(2) 0.051 Uiso 1 d . .
H11C H 0.297(3) 1.034(3) 0.5008(17) 0.051 Uiso 1 d . .
H11D H 0.221(2) 1.016(3) 0.582(2) 0.051 Uiso 1 d . .
H12C H 0.265(2) 1.258(3) 0.866(2) 0.051 Uiso 1 d . .
H12D H 0.324(3) 1.239(3) 0.9696(17) 0.051 Uiso 1 d . .
H13C H 0.997(2) 1.032(2) 0.370(2) 0.051 Uiso 1 d . .
H13D H 1.023(2) 1.131(2) 0.4820(17) 0.051 Uiso 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
Cu1 O2 2.0023(10) . ?
Cu1 N1 2.0081(12) . ?
Cu1 N2 2.0155(12) . ?
Cu1 N4 2.0241(12) . ?
Cu1 O1 2.2549(12) . ?
N4 C20 1.3468(19) . ?
N4 C16 1.3470(19) . ?
C20 C19 1.387(2) . ?
C20 H20 0.95 . ?
C19 C18 1.386(2) . ?
C19 H19 0.95 . ?
C18 C17 1.389(2) . ?
C18 H18 0.95 . ?
C17 C16 1.390(2) . ?
C17 H17 0.95 . ?
C16 C15 1.504(2) . ?
C15 N3 1.4547(18) . ?
C15 H15A 0.99 . ?
C15 H15B 0.99 . ?
N3 C7 1.3579(19) . ?
N3 C14 1.4579(18) . ?
C14 C13 1.493(2) . ?
C14 H14A 0.99 . ?
C14 H14B 0.99 . ?
C13 C12 1.388(2) . ?
C13 C8 1.399(2) . ?
C12 C11 1.387(2) . ?
C12 H12 0.95 . ?
C11 C10 1.393(2) . ?
C11 H11 0.95 . ?
C10 C9 1.393(2) . ?
C10 H10 0.95 . ?
C9 C8 1.400(2) . ?
C9 H9 0.95 . ?
C8 C7 1.4906(19) . ?
C7 N2 1.3060(19) . ?
N2 C6 1.4668(18) . ?
C6 C5 1.505(2) . ?
C6 H6A 0.99 . ?
C6 H6B 0.99 . ?
C5 N1 1.3420(19) . ?
C5 C4 1.391(2) . ?
C4 C3 1.385(2) . ?
C4 H4 0.95 . ?
C3 C2 1.389(2) . ?
C3 H3 0.95 . ?
C2 C1 1.382(2) . ?
C2 H2 0.95 . ?
C1 N1 1.3480(19) . ?
C1 H1 0.95 . ?
O2 C21 1.2872(19) . ?
C21 O3 1.2429(19) . ?
C21 C22 1.5099(19) . ?
C22 C24 1.397(2) . ?
C22 C23 1.397(2) . ?
C24 C23 1.389(2) 2 ?
C24 H24 0.95 . ?
C23 C24 1.389(2) 2 ?
C23 H23 0.95 . ?
O4 C25 1.253(2) . ?
C25 O5 1.2666(19) . ?
C25 C26 1.508(2) . ?
C26 C27 1.394(2) . ?
C26 C28 1.397(2) . ?
C27 C28 1.391(2) 2_765 ?
C27 H27 0.95 . ?
C28 C27 1.391(2) 2_765 ?
C28 H28 0.95 . ?
O1 H1A 0.921(17) . ?
O1 H1B 0.917(16) . ?
O6 H6C 0.911(17) . ?
O6 H6D 0.935(16) . ?
O7 H7C 0.912(17) . ?
O7 H7D 0.912(16) . ?
O8 H8C 0.928(16) . ?
O8 H8D 0.937(16) . ?
O9 H9C 0.938(17) . ?
O9 H9D 0.957(17) . ?
O10 H10C 0.910(16) . ?
O10 H10D 0.889(17) . ?
O11 H11C 0.937(16) . ?
O11 H11D 0.902(16) . ?
O12 H12C 0.905(16) . ?
O12 H12D 0.916(16) . ?
O13 H13C 0.921(17) . ?
O13 H13D 0.990(17) . ?

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
O2 Cu1 N1 91.09(5) . . ?
O2 Cu1 N2 161.39(5) . . ?
N1 Cu1 N2 82.28(5) . . ?
O2 Cu1 N4 89.46(5) . . ?
N1 Cu1 N4 172.32(5) . . ?
N2 Cu1 N4 99.43(5) . . ?
O2 Cu1 O1 99.46(5) . . ?
N1 Cu1 O1 81.92(5) . . ?
N2 Cu1 O1 96.82(5) . . ?
N4 Cu1 O1 90.43(5) . . ?
C20 N4 C16 118.66(13) . . ?
C20 N4 Cu1 119.24(10) . . ?
C16 N4 Cu1 122.03(10) . . ?
N4 C20 C19 122.58(14) . . ?
N4 C20 H20 118.7 . . ?
C19 C20 H20 118.7 . . ?
C18 C19 C20 118.44(14) . . ?
C18 C19 H19 120.8 . . ?
C20 C19 H19 120.8 . . ?
C19 C18 C17 119.48(14) . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C18 C17 C16 118.76(14) . . ?
C18 C17 H17 120.6 . . ?
C16 C17 H17 120.6 . . ?
N4 C16 C17 122.05(14) . . ?
N4 C16 C15 115.51(13) . . ?
C17 C16 C15 122.33(13) . . ?
N3 C15 C16 110.06(12) . . ?
N3 C15 H15A 109.6 . . ?
C16 C15 H15A 109.6 . . ?
N3 C15 H15B 109.6 . . ?
C16 C15 H15B 109.6 . . ?
H15A C15 H15B 108.2 . . ?
C7 N3 C15 125.28(12) . . ?
C7 N3 C14 113.98(12) . . ?
C15 N3 C14 120.74(12) . . ?
N3 C14 C13 101.80(12) . . ?
N3 C14 H14A 111.4 . . ?
C13 C14 H14A 111.4 . . ?
N3 C14 H14B 111.4 . . ?
C13 C14 H14B 111.4 . . ?
H14A C14 H14B 109.3 . . ?
C12 C13 C8 121.82(14) . . ?
C12 C13 C14 127.89(14) . . ?
C8 C13 C14 110.29(12) . . ?
C11 C12 C13 118.03(14) . . ?
C11 C12 H12 121 . . ?
C13 C12 H12 121 . . ?
C12 C11 C10 120.83(14) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C10 C9 121.27(15) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C10 C9 C8 118.15(14) . . ?
C10 C9 H9 120.9 . . ?
C8 C9 H9 120.9 . . ?
C13 C8 C9 119.86(13) . . ?
C13 C8 C7 107.37(12) . . ?
C9 C8 C7 132.77(14) . . ?
N2 C7 N3 122.42(13) . . ?
N2 C7 C8 131.34(13) . . ?
N3 C7 C8 106.24(12) . . ?
C7 N2 C6 117.35(12) . . ?
C7 N2 Cu1 130.57(10) . . ?
C6 N2 Cu1 110.48(9) . . ?
N2 C6 C5 110.72(11) . . ?
N2 C6 H6A 109.5 . . ?
C5 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
N1 C5 C4 121.69(14) . . ?
N1 C5 C6 117.31(13) . . ?
C4 C5 C6 120.97(13) . . ?
C3 C4 C5 119.03(14) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C4 C3 C2 119.28(14) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C1 C2 C3 118.62(14) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
N1 C1 C2 122.27(14) . . ?
N1 C1 H1 118.9 . . ?
C2 C1 H1 118.9 . . ?
C5 N1 C1 119.09(13) . . ?
C5 N1 Cu1 112.42(10) . . ?
C1 N1 Cu1 126.21(10) . . ?
C21 O2 Cu1 108.28(9) . . ?
O3 C21 O2 123.19(13) . . ?
O3 C21 C22 120.35(13) . . ?
O2 C21 C22 116.45(13) . . ?
C24 C22 C23 118.94(13) . . ?
C24 C22 C21 121.39(14) . . ?
C23 C22 C21 119.67(14) . . ?
C23 C24 C22 120.53(14) 2 . ?
C23 C24 H24 119.7 2 . ?
C22 C24 H24 119.7 . . ?
C24 C23 C22 120.53(14) 2 . ?
C24 C23 H23 119.7 2 . ?
C22 C23 H23 119.7 . . ?
O4 C25 O5 125.07(14) . . ?
O4 C25 C26 117.34(14) . . ?
O5 C25 C26 117.59(14) . . ?
C27 C26 C28 119.78(14) . . ?
C27 C26 C25 119.66(14) . . ?
C28 C26 C25 120.56(14) . . ?
C28 C27 C26 120.20(14) 2_765 . ?
C28 C27 H27 119.9 2_765 . ?
C26 C27 H27 119.9 . . ?
C27 C28 C26 120.02(14) 2_765 . ?
C27 C28 H28 120 2_765 . ?
C26 C28 H28 120 . . ?
Cu1 O1 H1A 130.2(17) . . ?
Cu1 O1 H1B 123.5(17) . . ?
H1A O1 H1B 105(2) . . ?
H6C O6 H6D 109(2) . . ?
H7C O7 H7D 112(2) . . ?
H8C O8 H8D 104(2) . . ?
H9C O9 H9D 96(2) . . ?
H10C O10 H10D 117(2) . . ?
H11C O11 H11D 125(2) . . ?
H12C O12 H12D 110(2) . . ?
H13C O13 H13D 99(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C16 N4 C20 C19 -0.7(2) . . . . ?
Cu1 N4 C20 C19 -177.81(11) . . . . ?
N4 C20 C19 C18 1.7(2) . . . . ?
C20 C19 C18 C17 -1.3(2) . . . . ?
C19 C18 C17 C16 0.0(2) . . . . ?
C20 N4 C16 C17 -0.7(2) . . . . ?
Cu1 N4 C16 C17 176.36(10) . . . . ?
C20 N4 C16 C15 175.67(12) . . . . ?
Cu1 N4 C16 C15 -7.32(16) . . . . ?
C18 C17 C16 N4 1.0(2) . . . . ?
C18 C17 C16 C15 -175.07(13) . . . . ?
N4 C16 C15 N3 -77.96(15) . . . . ?
C17 C16 C15 N3 98.35(16) . . . . ?
C16 C15 N3 C7 87.56(17) . . . . ?
C16 C15 N3 C14 -93.09(16) . . . . ?
C7 N3 C14 C13 5.14(16) . . . . ?
C15 N3 C14 C13 -174.27(12) . . . . ?
N3 C14 C13 C12 177.44(14) . . . . ?
N3 C14 C13 C8 -2.07(16) . . . . ?
C8 C13 C12 C11 2.0(2) . . . . ?
C14 C13 C12 C11 -177.42(15) . . . . ?
C13 C12 C11 C10 -1.7(2) . . . . ?
C12 C11 C10 C9 -0.1(3) . . . . ?
C11 C10 C9 C8 1.5(2) . . . . ?
C12 C13 C8 C9 -0.6(2) . . . . ?
C14 C13 C8 C9 178.92(13) . . . . ?
C12 C13 C8 C7 179.21(13) . . . . ?
C14 C13 C8 C7 -1.25(16) . . . . ?
C10 C9 C8 C13 -1.2(2) . . . . ?
C10 C9 C8 C7 179.05(15) . . . . ?
C15 N3 C7 N2 -6.8(2) . . . . ?
C14 N3 C7 N2 173.76(13) . . . . ?
C15 N3 C7 C8 173.35(13) . . . . ?
C14 N3 C7 C8 -6.04(16) . . . . ?
C13 C8 C7 N2 -175.42(15) . . . . ?
C9 C8 C7 N2 4.4(3) . . . . ?
C13 C8 C7 N3 4.35(16) . . . . ?
C9 C8 C7 N3 -175.85(16) . . . . ?
N3 C7 N2 C6 172.43(13) . . . . ?
C8 C7 N2 C6 -7.8(2) . . . . ?
N3 C7 N2 Cu1 -23.5(2) . . . . ?
C8 C7 N2 Cu1 156.20(12) . . . . ?
C7 N2 C6 C5 -172.17(12) . . . . ?
Cu1 N2 C6 C5 20.73(14) . . . . ?
N2 C6 C5 N1 -3.64(18) . . . . ?
N2 C6 C5 C4 178.04(13) . . . . ?
N1 C5 C4 C3 1.0(2) . . . . ?
C6 C5 C4 C3 179.20(14) . . . . ?
C5 C4 C3 C2 0.3(2) . . . . ?
C4 C3 C2 C1 -1.2(2) . . . . ?
C3 C2 C1 N1 1.1(2) . . . . ?
C4 C5 N1 C1 -1.1(2) . . . . ?
C6 C5 N1 C1 -179.45(13) . . . . ?
C4 C5 N1 Cu1 162.74(11) . . . . ?
C6 C5 N1 Cu1 -15.57(16) . . . . ?
C2 C1 N1 C5 0.1(2) . . . . ?
C2 C1 N1 Cu1 -161.35(12) . . . . ?
Cu1 O2 C21 O3 -4.71(17) . . . . ?
Cu1 O2 C21 C22 174.50(9) . . . . ?
O3 C21 C22 C24 179.48(14) . . . . ?
O2 C21 C22 C24 0.2(2) . . . . ?
O3 C21 C22 C23 -0.3(2) . . . . ?
O2 C21 C22 C23 -179.49(13) . . . . ?
C23 C22 C24 C23 -0.3(2) . . . 2 ?
C21 C22 C24 C23 179.96(13) . . . 2 ?
C24 C22 C23 C24 0.3(2) . . . 2 ?
C21 C22 C23 C24 -179.96(13) . . . 2 ?
O4 C25 C26 C27 -21.3(2) . . . . ?
O5 C25 C26 C27 158.57(14) . . . . ?
O4 C25 C26 C28 159.03(14) . . . . ?
O5 C25 C26 C28 -21.1(2) . . . . ?
C28 C26 C27 C28 -0.2(2) . . . 2_765 ?
C25 C26 C27 C28 -179.88(14) . . . 2_765 ?
C27 C26 C28 C27 0.2(2) . . . 2_765 ?
C25 C26 C28 C27 179.88(14) . . . 2_765 ?

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
C20 H20 O1 0.95 2.53 3.0637(19) 115.8 .
C20 H20 O12 0.95 2.52 3.2986(19) 139.2 1_544
C15 H15A O3 0.99 2.57 3.4790(18) 151.9 .
C15 H15B O8 0.99 2.61 3.261(2) 123.7 1_545
C6 H6A O6 0.99 2.4 3.381(2) 173.6 .
C1 H1 O2 0.95 2.49 3.0056(19) 114.5 .
O1 H1A O4 0.921(17) 1.783(17) 2.6852(16) 165(3) .
O1 H1B O7 0.917(16) 1.917(17) 2.8248(17) 170(2) .
O6 H6C O5 0.911(17) 1.949(17) 2.8514(17) 171(3) .
O6 H6D O11 0.935(16) 1.878(17) 2.803(2) 170(2) 2_676
O7 H7C O12 0.912(17) 1.882(17) 2.7892(17) 173(3) 2_676
O7 H7D O4 0.912(16) 1.875(17) 2.7803(17) 171(3) 2_665
O8 H8C O7 0.928(16) 1.890(18) 2.7839(18) 161(2) .
O8 H8D O11 0.937(16) 1.811(17) 2.744(2) 173(3) 2_676
O9 H9C O3 0.938(17) 1.874(17) 2.8063(17) 172(2) 1_565
O9 H9D O8 0.957(17) 1.862(18) 2.7805(19) 160(2) .
O10 H10C O5 0.910(16) 1.844(17) 2.7359(19) 166(3) 1_455
O10 H10D O9 0.889(17) 1.92(2) 2.727(2) 149(3) .
O11 H11C O9 0.937(16) 2.004(17) 2.940(2) 177(3) .
O11 H11D O13 0.902(16) 2.136(17) 3.036(2) 175(3) 2_676
O12 H12C O5 0.905(16) 1.860(17) 2.7603(16) 172(3) 2_676
O12 H12D O2 0.916(16) 2.062(17) 2.9709(16) 172(3) 1_566
O13 H13C O10 0.921(17) 2.00(2) 2.804(2) 145(2) 1_655
O13 H13D O6 0.990(17) 1.833(18) 2.811(2) 169(2) 2_776

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+:"~<>?|\-=[];'`,./
####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 980974'
_audit_update_record             
;
2015-02-13 deposited with the CCDC.
2015-02-27 downloaded from the CCDC.
;

#------------------ AUDIT DETAILS -------------------------------------------#

_audit_creation_date             2013-12-30
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#------------------  SECTION 2. COMPOUND(S) DETAILS -------------------------#


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

_chemical_name_systematic        
;
 ?
;
_chemical_name_common            'Compound 4'
_chemical_formula_moiety         'C28 H39 Co N4 O13'
_chemical_formula_sum            'C28 H39 Co N4 O13'
_chemical_formula_weight         698.56

#----------------------------------------------------------------------------#
#                   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                   11.6110(2)
_cell_length_b                   12.0270(3)
_cell_length_c                   13.7710(3)
_cell_angle_alpha                111.1880(10)
_cell_angle_beta                 107.0700(10)
_cell_angle_gamma                102.2380(10)
_cell_volume                     1601.22(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    16778
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      27.485

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

_exptl_crystal_description       prism
_exptl_crystal_colour            pink
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.11
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_F_000             734
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
5 -2 -1 0.081
-8 3 2 0.177
-1 -9 5 0.064
0 2 -1 0.107
2 12 -3 0.071
-1 -7 1 0.045


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

_exptl_absorpt_coefficient_mu    0.607
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   '(DENZO-SMN; Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min  0.863
_exptl_absorpt_correction_T_max  0.936

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

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_detector_area_resol_mean 9
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_ub_11      0.0216323
_diffrn_orient_matrix_ub_12      -0.0791424
_diffrn_orient_matrix_ub_13      -0.0159563
_diffrn_orient_matrix_ub_21      0.0928685
_diffrn_orient_matrix_ub_22      0.0518207
_diffrn_orient_matrix_ub_23      0.0273355
_diffrn_orient_matrix_ub_31      0.014478
_diffrn_orient_matrix_ub_32      0.0127618
_diffrn_orient_matrix_ub_33      0.0791343
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_number            26032
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.747
_diffrn_reflns_theta_max         27.463
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_reflns_number_total             7275
_reflns_number_gt                6425
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_computing_molecular_graphics    'Ortep (Johnson, 1976)'

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

_atom_sites_solution_hydrogens   mixed

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

_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 > 2σ(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.
 All hydrogen atoms joined to carbon atoms were positioned with an idealized 
 geometry and refined using a riding model with Uiso(H) fixed at 1.2 Ueq of C. 
 Hydrogen atoms of water molecule were found from the difference Fourier and 
 refined with restrained bond lengths and angles. Uiso(H) were constrained to 
 1.5 Ueq of their home O atom.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0349P)²+1.0287P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0074(9)
_refine_ls_number_reflns         7275
_refine_ls_number_parameters     470
_refine_ls_number_restraints     27
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0316
_refine_ls_wR_factor_ref         0.0827
_refine_ls_wR_factor_gt          0.0791
_refine_ls_goodness_of_fit_gt    11.537
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.48
_refine_diff_density_rms         0.069

#----------------------------------------------------------------------------#
#                   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'
Co Co 0.3494 0.9721 '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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.48526(2) 0.36342(2) 0.23931(2) 0.01281(7) Uani 1 d . .
N4 N 0.56931(12) 0.23096(12) 0.16717(11) 0.0142(2) Uani 1 d . .
C20 C 0.57235(14) 0.20850(15) 0.06507(13) 0.0170(3) Uani 1 d . .
H20 H 0.5364 0.251 0.027 0.02 Uiso 1 calc . .
C19 C 0.62682(15) 0.12474(15) 0.01392(14) 0.0201(3) Uani 1 d . .
H19 H 0.6292 0.1129 -0.0559 0.024 Uiso 1 calc . .
C18 C 0.67744(15) 0.05930(15) 0.06930(14) 0.0215(3) Uani 1 d . .
H18 H 0.7137 0.0019 0.0367 0.026 Uiso 1 calc . .
C17 C 0.67361(15) 0.08007(15) 0.17411(14) 0.0194(3) Uani 1 d . .
H17 H 0.7065 0.0364 0.2123 0.023 Uiso 1 calc . .
C16 C 0.61990(14) 0.16711(14) 0.22069(13) 0.0160(3) Uani 1 d . .
C15 C 0.61921(14) 0.20095(14) 0.33687(13) 0.0164(3) Uani 1 d . .
H15A H 0.5379 0.2105 0.3355 0.02 Uiso 1 calc . .
H15B H 0.6266 0.1322 0.3565 0.02 Uiso 1 calc . .
N3 N 0.72483(12) 0.31874(12) 0.42295(11) 0.0151(3) Uani 1 d . .
C14 C 0.84862(15) 0.31529(15) 0.48424(13) 0.0182(3) Uani 1 d . .
H14A H 0.8933 0.2911 0.435 0.022 Uiso 1 calc . .
H14B H 0.8384 0.2567 0.5171 0.022 Uiso 1 calc . .
C13 C 0.91782(15) 0.45013(15) 0.57444(13) 0.0162(3) Uani 1 d . .
C12 C 1.03947(15) 0.50224(16) 0.66171(14) 0.0193(3) Uani 1 d . .
H12 H 1.0911 0.4534 0.6672 0.023 Uiso 1 calc . .
C11 C 1.08222(15) 0.62904(16) 0.74058(14) 0.0211(3) Uani 1 d . .
H11 H 1.1629 0.6656 0.8009 0.025 Uiso 1 calc . .
C10 C 1.00548(15) 0.70222(16) 0.73034(14) 0.0221(3) Uani 1 d . .
H10 H 1.0358 0.7871 0.7843 0.026 Uiso 1 calc . .
C9 C 0.88464(15) 0.65127(15) 0.64126(14) 0.0190(3) Uani 1 d . .
H9 H 0.8347 0.7014 0.6344 0.023 Uiso 1 calc . .
C8 C 0.83988(14) 0.52270(14) 0.56209(12) 0.0143(3) Uani 1 d . .
C7 C 0.71727(14) 0.43716(14) 0.45991(12) 0.0134(3) Uani 1 d . .
N2 N 0.61738(12) 0.45969(12) 0.40839(11) 0.0141(2) Uani 1 d . .
C6 C 0.61758(14) 0.58985(14) 0.46362(13) 0.0156(3) Uani 1 d . .
H6A H 0.6909 0.6498 0.4669 0.019 Uiso 1 calc . .
H6B H 0.6273 0.6107 0.5412 0.019 Uiso 1 calc . .
C5 C 0.49542(14) 0.60426(15) 0.40110(13) 0.0158(3) Uani 1 d . .
C4 C 0.47858(16) 0.72113(16) 0.44236(14) 0.0204(3) Uani 1 d . .
H4 H 0.5427 0.791 0.5077 0.025 Uiso 1 calc . .
C3 C 0.36519(17) 0.73169(17) 0.38466(15) 0.0241(3) Uani 1 d . .
H3 H 0.3518 0.8087 0.4109 0.029 Uiso 1 calc . .
C2 C 0.27138(16) 0.62574(18) 0.28695(15) 0.0232(3) Uani 1 d . .
H2 H 0.1934 0.6299 0.2478 0.028 Uiso 1 calc . .
C1 C 0.29660(15) 0.51433(16) 0.24944(14) 0.0195(3) Uani 1 d . .
H1 H 0.2349 0.444 0.183 0.023 Uiso 1 calc . .
N1 N 0.40700(12) 0.50303(12) 0.30503(11) 0.0149(2) Uani 1 d . .
O2 O 0.30690(10) 0.25474(10) 0.09410(9) 0.0182(2) Uani 1 d . .
C21 C 0.25957(14) 0.18683(14) 0.13509(13) 0.0161(3) Uani 1 d . .
O3 O 0.32453(10) 0.19952(11) 0.23215(9) 0.0191(2) Uani 1 d . .
C22 C 0.12473(14) 0.09055(14) 0.06547(13) 0.0154(3) Uani 1 d . .
C24 C 0.05968(14) 0.06572(15) -0.04741(14) 0.0179(3) Uani 1 d . .
H24 H 0.0994 0.11 -0.0789 0.021 Uiso 1 calc . .
C23 C 0.06396(15) 0.02478(15) 0.11250(13) 0.0183(3) Uani 1 d . .
H23 H 0.1065 0.0416 0.1878 0.022 Uiso 1 calc . .
O4 O 0.73784(11) 0.48413(11) 0.09563(10) 0.0218(2) Uani 1 d . .
C25 C 0.84120(15) 0.57019(16) 0.12287(13) 0.0177(3) Uani 1 d . .
O5 O 0.88098(11) 0.68420(11) 0.19967(10) 0.0212(2) Uani 1 d . .
C26 C 0.92347(14) 0.53412(15) 0.05864(13) 0.0164(3) Uani 1 d . .
C27 C 0.91171(15) 0.40703(15) 0.00544(14) 0.0186(3) Uani 1 d . .
H27 H 0.8524 0.3447 0.0089 0.022 Uiso 1 calc . .
C28 C 1.01213(15) 0.62738(16) 0.05278(14) 0.0187(3) Uani 1 d . .
H28 H 1.0202 0.7125 0.0878 0.022 Uiso 1 calc . .
O1 O 0.55859(11) 0.47900(11) 0.17771(10) 0.0200(2) Uani 1 d . .
O6 O 0.83432(15) 0.76429(14) 0.40232(13) 0.0362(3) Uani 1 d . .
O7 O 0.46399(12) 0.64840(12) 0.12453(11) 0.0233(3) Uani 1 d . .
O8 O 0.50538(16) 0.89818(14) 0.27981(15) 0.0384(3) Uani 1 d . .
O9 O 0.31425(15) 0.99281(16) 0.29331(16) 0.0440(4) Uani 1 d . .
O10 O 0.10567(14) 0.89973(15) 0.33364(13) 0.0409(4) Uani 1 d . .
O11 O 0.23764(15) 1.02029(15) 0.57398(14) 0.0399(3) Uani 1 d . .
O12 O 0.31419(11) 1.22810(12) 0.88360(11) 0.0236(3) Uani 1 d . .
O13 O 0.97064(16) 1.07365(15) 0.37872(15) 0.0435(4) Uani 1 d . .
H1A H 0.626(2) 0.484(3) 0.156(2) 0.065 Uiso 1 d . .
H1B H 0.523(3) 0.538(2) 0.166(2) 0.065 Uiso 1 d . .
H6C H 0.846(3) 0.732(3) 0.3343(18) 0.065 Uiso 1 d . .
H6D H 0.805(3) 0.833(2) 0.405(2) 0.065 Uiso 1 d . .
H7C H 0.535(2) 0.686(3) 0.114(2) 0.065 Uiso 1 d . .
H7D H 0.392(2) 0.611(3) 0.0559(18) 0.065 Uiso 1 d . .
H8C H 0.471(3) 0.8134(18) 0.229(2) 0.065 Uiso 1 d . .
H8D H 0.5883(19) 0.922(3) 0.332(2) 0.065 Uiso 1 d . .
H9C H 0.318(3) 1.058(2) 0.272(3) 0.065 Uiso 1 d . .
H9D H 0.365(3) 0.950(3) 0.271(2) 0.065 Uiso 1 d . .
H10C H 0.042(2) 0.821(2) 0.281(2) 0.065 Uiso 1 d . .
H10D H 0.176(2) 0.913(3) 0.315(2) 0.065 Uiso 1 d . .
H11C H 0.215(3) 0.981(3) 0.4956(15) 0.065 Uiso 1 d . .
H11D H 0.170(2) 0.986(3) 0.596(2) 0.065 Uiso 1 d . .
H12C H 0.249(2) 1.251(3) 0.849(2) 0.065 Uiso 1 d . .
H12D H 0.313(3) 1.243(3) 0.9541(17) 0.065 Uiso 1 d . .
H13C H 1.008(3) 1.010(2) 0.356(2) 0.065 Uiso 1 d . .
H13D H 1.031(2) 1.139(2) 0.4560(17) 0.065 Uiso 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
Co1 O1 2.0375(11) . ?
Co1 N2 2.0776(13) . ?
Co1 N1 2.1203(13) . ?
Co1 O2 2.1279(11) . ?
Co1 N4 2.1357(12) . ?
Co1 O3 2.3602(11) . ?
N4 C20 1.345(2) . ?
N4 C16 1.350(2) . ?
C20 C19 1.389(2) . ?
C20 H20 0.93 . ?
C19 C18 1.383(2) . ?
C19 H19 0.93 . ?
C18 C17 1.389(2) . ?
C18 H18 0.93 . ?
C17 C16 1.387(2) . ?
C17 H17 0.93 . ?
C16 C15 1.505(2) . ?
C15 N3 1.4533(19) . ?
C15 H15A 0.97 . ?
C15 H15B 0.97 . ?
N3 C7 1.3603(19) . ?
N3 C14 1.4554(19) . ?
C14 C13 1.491(2) . ?
C14 H14A 0.97 . ?
C14 H14B 0.97 . ?
C13 C12 1.384(2) . ?
C13 C8 1.401(2) . ?
C12 C11 1.385(2) . ?
C12 H12 0.93 . ?
C11 C10 1.392(2) . ?
C11 H11 0.93 . ?
C10 C9 1.389(2) . ?
C10 H10 0.93 . ?
C9 C8 1.399(2) . ?
C9 H9 0.93 . ?
C8 C7 1.491(2) . ?
C7 N2 1.3081(19) . ?
N2 C6 1.4717(19) . ?
C6 C5 1.509(2) . ?
C6 H6A 0.97 . ?
C6 H6B 0.97 . ?
C5 N1 1.340(2) . ?
C5 C4 1.393(2) . ?
C4 C3 1.382(2) . ?
C4 H4 0.93 . ?
C3 C2 1.390(3) . ?
C3 H3 0.93 . ?
C2 C1 1.379(2) . ?
C2 H2 0.93 . ?
C1 N1 1.3493(19) . ?
C1 H1 0.93 . ?
O2 C21 1.270(2) . ?
C21 O3 1.2612(19) . ?
C21 C22 1.503(2) . ?
C22 C23 1.395(2) . ?
C22 C24 1.398(2) . ?
C24 C23 1.388(2) 2 ?
C24 H24 0.93 . ?
C23 C24 1.388(2) 2 ?
C23 H23 0.93 . ?
O4 C25 1.257(2) . ?
C25 O5 1.268(2) . ?
C25 C26 1.509(2) . ?
C26 C27 1.391(2) . ?
C26 C28 1.396(2) . ?
C27 C28 1.388(2) 2_765 ?
C27 H27 0.93 . ?
C28 C27 1.388(2) 2_765 ?
C28 H28 0.93 . ?
O1 H1A 0.916(17) . ?
O1 H1B 0.927(17) . ?
O6 H6C 0.935(17) . ?
O6 H6D 0.952(17) . ?
O7 H7C 0.924(17) . ?
O7 H7D 0.932(17) . ?
O8 H8C 0.916(17) . ?
O8 H8D 0.925(17) . ?
O9 H9C 0.928(17) . ?
O9 H9D 0.906(17) . ?
O10 H10C 0.927(17) . ?
O10 H10D 0.926(17) . ?
O11 H11C 0.932(17) . ?
O11 H11D 0.982(17) . ?
O12 H12C 0.921(17) . ?
O12 H12D 0.927(17) . ?
O13 H13C 0.959(17) . ?
O13 H13D 0.983(17) . ?

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 Co1 N2 100.01(5) . . ?
O1 Co1 N1 85.15(5) . . ?
N2 Co1 N1 80.11(5) . . ?
O1 Co1 O2 95.96(5) . . ?
N2 Co1 O2 160.22(5) . . ?
N1 Co1 O2 89.74(5) . . ?
O1 Co1 N4 90.52(5) . . ?
N2 Co1 N4 100.98(5) . . ?
N1 Co1 N4 175.66(5) . . ?
O2 Co1 N4 90.42(4) . . ?
O1 Co1 O3 154.34(5) . . ?
N2 Co1 O3 104.83(4) . . ?
N1 Co1 O3 92.80(4) . . ?
O2 Co1 O3 58.42(4) . . ?
N4 Co1 O3 90.98(4) . . ?
C20 N4 C16 117.97(13) . . ?
C20 N4 Co1 119.98(10) . . ?
C16 N4 Co1 122.04(10) . . ?
N4 C20 C19 122.94(15) . . ?
N4 C20 H20 118.5 . . ?
C19 C20 H20 118.5 . . ?
C18 C19 C20 118.46(15) . . ?
C18 C19 H19 120.8 . . ?
C20 C19 H19 120.8 . . ?
C19 C18 C17 119.36(15) . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C16 C17 C18 118.76(15) . . ?
C16 C17 H17 120.6 . . ?
C18 C17 H17 120.6 . . ?
N4 C16 C17 122.49(15) . . ?
N4 C16 C15 115.40(13) . . ?
C17 C16 C15 122.07(14) . . ?
N3 C15 C16 111.27(12) . . ?
N3 C15 H15A 109.4 . . ?
C16 C15 H15A 109.4 . . ?
N3 C15 H15B 109.4 . . ?
C16 C15 H15B 109.4 . . ?
H15A C15 H15B 108 . . ?
C7 N3 C15 125.42(12) . . ?
C7 N3 C14 114.16(12) . . ?
C15 N3 C14 120.24(12) . . ?
N3 C14 C13 101.96(12) . . ?
N3 C14 H14A 111.4 . . ?
C13 C14 H14A 111.4 . . ?
N3 C14 H14B 111.4 . . ?
C13 C14 H14B 111.4 . . ?
H14A C14 H14B 109.2 . . ?
C12 C13 C8 122.01(15) . . ?
C12 C13 C14 127.88(14) . . ?
C8 C13 C14 110.09(13) . . ?
C13 C12 C11 118.20(15) . . ?
C13 C12 H12 120.9 . . ?
C11 C12 H12 120.9 . . ?
C12 C11 C10 120.54(15) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C9 C10 C11 121.48(15) . . ?
C9 C10 H10 119.3 . . ?
C11 C10 H10 119.3 . . ?
C10 C9 C8 118.36(15) . . ?
C10 C9 H9 120.8 . . ?
C8 C9 H9 120.8 . . ?
C9 C8 C13 119.37(14) . . ?
C9 C8 C7 133.02(14) . . ?
C13 C8 C7 107.61(13) . . ?
N2 C7 N3 122.35(13) . . ?
N2 C7 C8 131.74(14) . . ?
N3 C7 C8 105.91(12) . . ?
C7 N2 C6 116.30(12) . . ?
C7 N2 Co1 129.80(10) . . ?
C6 N2 Co1 111.04(9) . . ?
N2 C6 C5 112.23(12) . . ?
N2 C6 H6A 109.2 . . ?
C5 C6 H6A 109.2 . . ?
N2 C6 H6B 109.2 . . ?
C5 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
N1 C5 C4 122.01(14) . . ?
N1 C5 C6 118.00(13) . . ?
C4 C5 C6 119.97(14) . . ?
C3 C4 C5 119.00(16) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C4 C3 C2 119.18(16) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C1 C2 C3 118.48(15) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 H2 120.8 . . ?
N1 C1 C2 122.81(15) . . ?
N1 C1 H1 118.6 . . ?
C2 C1 H1 118.6 . . ?
C5 N1 C1 118.47(14) . . ?
C5 N1 Co1 111.84(10) . . ?
C1 N1 Co1 127.44(11) . . ?
C21 O2 Co1 95.59(9) . . ?
O3 C21 O2 120.71(14) . . ?
O3 C21 C22 120.58(14) . . ?
O2 C21 C22 118.71(14) . . ?
C21 O3 Co1 85.23(9) . . ?
C23 C22 C24 119.55(14) . . ?
C23 C22 C21 120.38(14) . . ?
C24 C22 C21 120.07(14) . . ?
C23 C24 C22 120.17(15) 2 . ?
C23 C24 H24 119.9 2 . ?
C22 C24 H24 119.9 . . ?
C24 C23 C22 120.28(15) 2 . ?
C24 C23 H23 119.9 2 . ?
C22 C23 H23 119.9 . . ?
O4 C25 O5 125.03(14) . . ?
O4 C25 C26 117.04(14) . . ?
O5 C25 C26 117.93(14) . . ?
C27 C26 C28 119.60(14) . . ?
C27 C26 C25 119.82(14) . . ?
C28 C26 C25 120.58(14) . . ?
C28 C27 C26 120.47(15) 2_765 . ?
C28 C27 H27 119.8 2_765 . ?
C26 C27 H27 119.8 . . ?
C27 C28 C26 119.93(15) 2_765 . ?
C27 C28 H28 120 2_765 . ?
C26 C28 H28 120 . . ?
Co1 O1 H1A 129.8(18) . . ?
Co1 O1 H1B 121.6(18) . . ?
H1A O1 H1B 109(2) . . ?
H6C O6 H6D 107(2) . . ?
H7C O7 H7D 109(2) . . ?
H8C O8 H8D 113(2) . . ?
H9C O9 H9D 110(2) . . ?
H10C O10 H10D 111(2) . . ?
H11C O11 H11D 113(2) . . ?
H12C O12 H12D 105(2) . . ?
H13C O13 H13D 107(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C16 N4 C20 C19 -1.1(2) . . . . ?
Co1 N4 C20 C19 179.24(11) . . . . ?
N4 C20 C19 C18 1.6(2) . . . . ?
C20 C19 C18 C17 -0.7(2) . . . . ?
C19 C18 C17 C16 -0.6(2) . . . . ?
C20 N4 C16 C17 -0.3(2) . . . . ?
Co1 N4 C16 C17 179.40(11) . . . . ?
C20 N4 C16 C15 177.24(13) . . . . ?
Co1 N4 C16 C15 -3.11(17) . . . . ?
C18 C17 C16 N4 1.1(2) . . . . ?
C18 C17 C16 C15 -176.25(14) . . . . ?
N4 C16 C15 N3 -79.75(16) . . . . ?
C17 C16 C15 N3 97.75(17) . . . . ?
C16 C15 N3 C7 94.36(17) . . . . ?
C16 C15 N3 C14 -90.80(16) . . . . ?
C7 N3 C14 C13 4.52(17) . . . . ?
C15 N3 C14 C13 -170.88(13) . . . . ?
N3 C14 C13 C12 177.10(15) . . . . ?
N3 C14 C13 C8 -1.43(17) . . . . ?
C8 C13 C12 C11 2.1(2) . . . . ?
C14 C13 C12 C11 -176.23(16) . . . . ?
C13 C12 C11 C10 -1.4(2) . . . . ?
C12 C11 C10 C9 -0.2(3) . . . . ?
C11 C10 C9 C8 1.1(3) . . . . ?
C10 C9 C8 C13 -0.4(2) . . . . ?
C10 C9 C8 C7 178.41(16) . . . . ?
C12 C13 C8 C9 -1.2(2) . . . . ?
C14 C13 C8 C9 177.40(14) . . . . ?
C12 C13 C8 C7 179.67(14) . . . . ?
C14 C13 C8 C7 -1.71(17) . . . . ?
C15 N3 C7 N2 -10.9(2) . . . . ?
C14 N3 C7 N2 174.03(14) . . . . ?
C15 N3 C7 C8 169.48(13) . . . . ?
C14 N3 C7 C8 -5.64(17) . . . . ?
C9 C8 C7 N2 5.8(3) . . . . ?
C13 C8 C7 N2 -175.23(15) . . . . ?
C9 C8 C7 N3 -174.54(16) . . . . ?
C13 C8 C7 N3 4.39(16) . . . . ?
N3 C7 N2 C6 174.85(13) . . . . ?
C8 C7 N2 C6 -5.6(2) . . . . ?
N3 C7 N2 Co1 -26.2(2) . . . . ?
C8 C7 N2 Co1 153.33(12) . . . . ?
C7 N2 C6 C5 -177.01(13) . . . . ?
Co1 N2 C6 C5 20.22(14) . . . . ?
N2 C6 C5 N1 -2.13(19) . . . . ?
N2 C6 C5 C4 179.28(13) . . . . ?
N1 C5 C4 C3 2.4(2) . . . . ?
C6 C5 C4 C3 -179.09(15) . . . . ?
C5 C4 C3 C2 -0.2(2) . . . . ?
C4 C3 C2 C1 -1.7(2) . . . . ?
C3 C2 C1 N1 1.6(2) . . . . ?
C4 C5 N1 C1 -2.4(2) . . . . ?
C6 C5 N1 C1 179.00(13) . . . . ?
C4 C5 N1 Co1 161.79(12) . . . . ?
C6 C5 N1 Co1 -16.77(16) . . . . ?
C2 C1 N1 C5 0.4(2) . . . . ?
C2 C1 N1 Co1 -161.07(12) . . . . ?
Co1 O2 C21 O3 -2.32(15) . . . . ?
Co1 O2 C21 C22 177.94(11) . . . . ?
O2 C21 O3 Co1 2.09(14) . . . . ?
C22 C21 O3 Co1 -178.18(13) . . . . ?
O3 C21 C22 C23 7.7(2) . . . . ?
O2 C21 C22 C23 -172.54(14) . . . . ?
O3 C21 C22 C24 -171.84(14) . . . . ?
O2 C21 C22 C24 7.9(2) . . . . ?
C23 C22 C24 C23 -0.7(3) . . . 2 ?
C21 C22 C24 C23 178.85(14) . . . 2 ?
C24 C22 C23 C24 0.7(3) . . . 2 ?
C21 C22 C23 C24 -178.85(14) . . . 2 ?
O4 C25 C26 C27 -23.1(2) . . . . ?
O5 C25 C26 C27 156.96(15) . . . . ?
O4 C25 C26 C28 157.35(15) . . . . ?
O5 C25 C26 C28 -22.6(2) . . . . ?
C28 C26 C27 C28 0.3(3) . . . 2_765 ?
C25 C26 C27 C28 -179.21(14) . . . 2_765 ?
C27 C26 C28 C27 -0.3(3) . . . 2_765 ?
C25 C26 C28 C27 179.21(14) . . . 2_765 ?

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
C20 H20 O12 0.93 2.64 3.408(2) 140.8 1_544
C15 H15A O3 0.97 2.42 3.2934(19) 150.3 .
C15 H15B O8 0.97 2.51 3.302(2) 138.4 1_545
C6 H6A O6 0.97 2.5 3.426(2) 160 .
C1 H1 O2 0.93 2.6 3.133(2) 116.8 .
O1 H1A O4 0.916(17) 1.734(17) 2.6440(15) 172(3) .
O8 H8C O7 0.916(17) 1.95(2) 2.8230(19) 159(3) .
O7 H7C O12 0.924(17) 1.825(17) 2.7423(17) 172(3) 2_676
O9 H9C O3 0.928(17) 1.962(17) 2.8898(19) 177(3) 1_565
O7 H7D O4 0.932(17) 1.904(18) 2.8243(18) 169(3) 2_665
O1 H1B O7 0.927(17) 1.811(18) 2.7292(16) 170(3) .
O12 H12C O5 0.921(17) 1.901(17) 2.8152(17) 172(3) 2_676
O6 H6C O5 0.935(17) 1.928(17) 2.8592(18) 174(3) .
O10 H10C O5 0.927(17) 1.898(18) 2.7891(19) 161(3) 1_455
O12 H12D O2 0.927(17) 1.905(17) 2.8279(17) 173(3) 1_566
O6 H6D O11 0.952(17) 1.877(17) 2.825(2) 174(3) 2_676
O13 H13C O10 0.959(17) 1.919(18) 2.871(2) 171(3) 1_655
O9 H9D O8 0.906(17) 1.856(19) 2.723(2) 160(3) .
O13 H13D O6 0.983(17) 1.845(19) 2.809(2) 166(3) 2_776
O10 H10D O9 0.926(17) 1.851(19) 2.742(2) 161(3) .
O8 H8D O11 0.925(17) 1.860(17) 2.779(2) 172(3) 2_676
O11 H11C O10 0.932(17) 1.94(2) 2.831(2) 158(3) .
O11 H11D O13 0.982(17) 1.827(18) 2.801(2) 172(3) 2_676
C20 H20 O12 0.93 2.64 3.408(2) 140.8 1_544
C15 H15A O3 0.97 2.42 3.2934(19) 150.3 .
C15 H15B O8 0.97 2.51 3.302(2) 138.4 1_545
C6 H6A O6 0.97 2.5 3.426(2) 160 .
C1 H1 O2 0.93 2.6 3.133(2) 116.8 .
O1 H1A O4 0.916(17) 1.734(17) 2.6440(15) 172(3) .
O1 H1B O7 0.927(17) 1.811(18) 2.7292(16) 170(3) .
O6 H6C O5 0.935(17) 1.928(17) 2.8592(18) 174(3) .
O6 H6D O11 0.952(17) 1.877(17) 2.825(2) 174(3) 2_676
O7 H7C O12 0.924(17) 1.825(17) 2.7423(17) 172(3) 2_676
O7 H7D O4 0.932(17) 1.904(18) 2.8243(18) 169(3) 2_665
O8 H8C O7 0.916(17) 1.95(2) 2.8230(19) 159(3) .
O8 H8D O11 0.925(17) 1.860(17) 2.779(2) 172(3) 2_676
O9 H9C O3 0.928(17) 1.962(17) 2.8898(19) 177(3) 1_565
O9 H9D O8 0.906(17) 1.856(19) 2.723(2) 160(3) .
O10 H10C O5 0.927(17) 1.898(18) 2.7891(19) 161(3) 1_455
O10 H10D O9 0.926(17) 1.851(19) 2.742(2) 161(3) .
O11 H11C O10 0.932(17) 1.94(2) 2.831(2) 158(3) .
O11 H11D O13 0.982(17) 1.827(18) 2.801(2) 172(3) 2_676
O12 H12C O5 0.921(17) 1.901(17) 2.8152(17) 172(3) 2_676
O12 H12D O2 0.927(17) 1.905(17) 2.8279(17) 173(3) 1_566
O13 H13C O10 0.959(17) 1.919(18) 2.871(2) 171(3) 1_655
O13 H13D O6 0.983(17) 1.845(19) 2.809(2) 166(3) 2_776

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+:"~<>?|\-=[];'`,./

####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 1023714'
_audit_update_record             
;
2015-02-24 deposited with the CCDC.
2015-02-27 downloaded from the CCDC.
;

_audit_creation_date             2015-02-20T18:24:58-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_name_systematic        5
_chemical_formula_moiety         'C24 H22 Co N4 O4, 1.6(O), H2 O'
_chemical_formula_sum            'C24 H27.20 Co N4 O6.60'
_chemical_formula_weight         536.23

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.8607(4)
_cell_length_b                   10.3695(5)
_cell_length_c                   20.7248(9)
_cell_angle_alpha                90
_cell_angle_beta                 96.103(3)
_cell_angle_gamma                90
_cell_volume                     2320.80(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9739
_cell_measurement_theta_min      2.8279
_cell_measurement_theta_max      28.6688

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

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.295
_exptl_crystal_size_mid          0.287
_exptl_crystal_size_min          0.126
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_F_000             1116.0
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -5 27 0.1277
-15 2 0 0.0689
8 -8 17 0.0969
0 14 5 0.1409
2 -13 -14 0.1405
-8 12 9 0.1334
11 -10 -11 0.1264
-2 0 29 0.1423
-11 10 6 0.1182
7 1 -27 0.1464
15 -3 -9 0.0954
12 -8 9 0.0819
-9 -4 24 0.1349
-15 4 6 0.0905
15 -1 -1 0.0679
-15 1 2 0.0682
14 5 -2 0.098
14 -1 7 0.0557
11 -6 14 0.0757
-15 -3 -1 0.0682
-14 0 -6 0.0661
11 10 2 0.125
-12 -8 -4 0.1003
11 3 17 0.093
-8 -12 -7 0.123
-11 -1 -18 0.0919
8 3 22 0.1079
-2 -14 -10 0.1344
-8 9 -17 0.0934
7 -4 23 0.0889
-6 0 -25 0.1129

_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.792
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
        (compiled Feb  1 2013,16:14:44)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.61572
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.8
_shelx_estimated_absorpt_T_max   0.907

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

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  mirror
_diffrn_detector_area_resol_mean 10.3756
_diffrn_orient_matrix_ub_11      0.0527405
_diffrn_orient_matrix_ub_12      0.0381198
_diffrn_orient_matrix_ub_13      -0.0042706
_diffrn_orient_matrix_ub_21      -0.0123514
_diffrn_orient_matrix_ub_22      0.0390731
_diffrn_orient_matrix_ub_23      0.026642
_diffrn_orient_matrix_ub_31      0.0371888
_diffrn_orient_matrix_ub_32      -0.0411568
_diffrn_orient_matrix_ub_33      0.021382
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0901
_diffrn_reflns_av_unetI/netI     0.1018
_diffrn_reflns_number            33308
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.965
_diffrn_reflns_theta_max         28.669
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.942
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.942
_reflns_number_total             5633
_reflns_number_gt                3806
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
        (compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
        (compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
        (compiled Feb  1 2013,16:14:44)
;
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'

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

_atom_sites_solution_hydrogens   mixed

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

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0460P)²+2.5332P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5633
_refine_ls_number_parameters     351
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0891
_refine_ls_R_factor_gt           0.0541
_refine_ls_wR_factor_ref         0.1409
_refine_ls_wR_factor_gt          0.1214
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.561
_refine_diff_density_min         -0.554
_refine_diff_density_rms         0.07

#----------------------------------------------------------------------------#
#                   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'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.12880(3) 0.93878(5) 0.14836(2) 0.04000(15) Uani 1 d . .
N1 N -0.0087(2) 0.8210(2) 0.09840(12) 0.0327(5) Uani 1 d . .
N2 N 0.1630(2) 0.9740(2) 0.05296(11) 0.0303(5) Uani 1 d . .
N3 N 0.2846(2) 1.1605(2) 0.06235(13) 0.0366(6) Uani 1 d . .
N4 N 0.2673(2) 1.0519(3) 0.20078(13) 0.0514(8) Uani 1 d . .
C1 C -0.1018(3) 0.7572(3) 0.12276(16) 0.0393(7) Uani 1 d . .
H1 H -0.1263 0.7835 0.1634 0.047 Uiso 1 calc . .
C2 C -0.1623(3) 0.6558(3) 0.09096(17) 0.0445(8) Uani 1 d . .
H2 H -0.228 0.6132 0.1091 0.053 Uiso 1 calc . .
C3 C -0.1260(3) 0.6161(3) 0.03158(18) 0.0436(8) Uani 1 d . .
H3 H -0.1643 0.544 0.0094 0.052 Uiso 1 calc . .
C4 C -0.0335(3) 0.6832(3) 0.00554(15) 0.0361(7) Uani 1 d . .
H4 H -0.008 0.659 -0.0352 0.043 Uiso 1 calc . .
C5 C 0.0220(2) 0.7869(3) 0.03993(14) 0.0303(6) Uani 1 d . .
C6 C 0.1225(2) 0.8635(3) 0.01189(13) 0.0296(6) Uani 1 d . .
H6A H 0.1943 0.8066 0.0074 0.036 Uiso 1 calc . .
H6B H 0.091 0.8947 -0.0319 0.036 Uiso 1 calc . .
C7 C 0.2451(2) 1.0504(3) 0.03093(13) 0.0268(6) Uani 1 d . .
C8 C 0.3151(2) 1.0409(3) -0.02669(13) 0.0274(6) Uani 1 d . .
C9 C 0.3110(2) 0.9530(3) -0.07785(14) 0.0319(6) Uani 1 d . .
H9 H 0.2521 0.885 -0.0815 0.038 Uiso 1 calc . .
C10 C 0.3950(3) 0.9675(3) -0.12314(15) 0.0398(7) Uani 1 d . .
H10 H 0.3929 0.9089 -0.1585 0.048 Uiso 1 calc . .
C11 C 0.4822(3) 1.0657(3) -0.11811(16) 0.0421(8) Uani 1 d . .
H11 H 0.5401 1.0721 -0.1492 0.051 Uiso 1 calc . .
C12 C 0.4854(3) 1.1536(3) -0.06853(16) 0.0394(7) Uani 1 d . .
H12 H 0.5446 1.2214 -0.0652 0.047 Uiso 1 calc . .
C13 C 0.4009(2) 1.1416(3) -0.02346(14) 0.0317(6) Uani 1 d . .
C14 C 0.3856(3) 1.2237(3) 0.03390(16) 0.0391(7) Uani 1 d . .
H14A H 0.462 1.2249 0.0645 0.047 Uiso 1 calc . .
H14B H 0.3634 1.3133 0.0208 0.047 Uiso 1 calc . .
C15 C 0.2338(3) 1.2157(3) 0.11811(17) 0.0473(9) Uani 1 d . .
H15A H 0.1451 1.1924 0.1166 0.057 Uiso 1 calc . .
H15B H 0.2395 1.3109 0.1161 0.057 Uiso 1 calc . .
C16 C 0.3006(3) 1.1695(4) 0.18094(17) 0.0506(9) Uani 1 d . .
C17 C 0.3956(3) 1.2397(5) 0.2148(2) 0.0678(13) Uani 1 d . .
H17 H 0.4173 1.3226 0.2001 0.081 Uiso 1 calc . .
C18 C 0.4581(4) 1.1872(6) 0.2702(2) 0.0795(16) Uani 1 d . .
H18 H 0.5249 1.2325 0.2933 0.095 Uiso 1 calc . .
C19 C 0.4227(3) 1.0691(6) 0.29146(19) 0.0723(15) Uani 1 d . .
H19 H 0.4636 1.0323 0.3299 0.087 Uiso 1 calc . .
C20 C 0.3265(3) 1.0039(5) 0.25606(16) 0.0647(12) Uani 1 d . .
H20 H 0.3015 0.9226 0.2713 0.078 Uiso 1 calc . .
O1A O -0.0132(3) 1.0961(4) 0.16298(18) 0.0344(10) Uiso 0.67 d A 1
O2A O 0.0296(3) 0.9517(4) 0.24007(16) 0.0352(8) Uiso 0.67 d A 1
O3A O -0.2432(3) 1.2689(4) 0.34423(18) 0.0338(9) Uiso 0.67 d A 1
O4A O -0.2843(4) 1.0981(5) 0.3996(3) 0.0874(17) Uani 0.67 d A 1
C21A C -0.0301(4) 1.0488(5) 0.2174(2) 0.0318(9) Uiso 0.67 d A 1
C22A C -0.1218(5) 1.1194(7) 0.2556(2) 0.0544(15) Uani 0.67 d A 1
H22A H -0.0913 1.2087 0.2627 0.065 Uiso 0.67 calc A 1
H22B H -0.2013 1.1248 0.2275 0.065 Uiso 0.67 calc A 1
C23A C -0.1486(4) 1.0673(5) 0.3193(2) 0.0419(11) Uani 0.67 d A 1
H23A H -0.0693 1.0538 0.3467 0.05 Uiso 0.67 calc A 1
H23B H -0.1891 0.9821 0.3124 0.05 Uiso 0.67 calc A 1
C24A C -0.2315(4) 1.1538(6) 0.3560(3) 0.0391(11) Uani 0.67 d A 1
O1B O -0.0164(6) 1.0589(7) 0.1729(3) 0.0278(17) Uiso 0.33 d A 2
O2B O 0.0468(6) 0.8951(7) 0.2357(3) 0.0341(15) Uiso 0.33 d A 2
O3B O -0.2475(6) 1.3131(7) 0.3383(3) 0.0302(18) Uiso 0.33 d A 2
O4B O -0.2855(9) 1.0927(9) 0.3559(4) 0.050(2) Uiso 0.33 d A 2
C21B C -0.0220(9) 0.9953(10) 0.2255(4) 0.0318(9) Uiso 0.33 d A 2
C22B C -0.1154(9) 1.0201(9) 0.2727(5) 0.041(2) Uiso 0.33 d A 2
H22C H -0.0772 1.0001 0.3171 0.049 Uiso 0.33 calc A 2
H22D H -0.1865 0.961 0.2628 0.049 Uiso 0.33 calc A 2
C23B C -0.1623(9) 1.1572(9) 0.2712(5) 0.033(2) Uiso 0.33 d A 2
H23C H -0.2137 1.1717 0.2295 0.04 Uiso 0.33 calc A 2
H23D H -0.0905 1.2163 0.2728 0.04 Uiso 0.33 calc A 2
C24B C -0.2397(10) 1.1922(13) 0.3272(6) 0.041(3) Uiso 0.33 d A 2
O6C O -0.3453(5) 1.1066(6) 0.5367(3) 0.0481(14) Uani 0.4 d B 3
O6B O -0.4017(7) 1.0539(7) 0.4592(4) 0.0436(13) Uiso 0.3 d C 2
O5 O 0.1114(3) 0.8306(3) 0.36521(13) 0.0627(7) Uani 1 d . .
O7 O -0.3533(4) 1.1238(5) 0.6011(3) 0.0748(15) Uani 0.6 d D 1
O6A O -0.4326(7) 1.0386(7) 0.4861(4) 0.0436(13) Uiso 0.3 d E 1
H5A H 0.091(4) 0.874(3) 0.3283(14) 0.087(15) Uiso 1 d . .
H5B H 0.078(3) 0.756(2) 0.3555(15) 0.033(9) Uiso 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
Co1 O3B 1.833(7) 2_545 ?
Co1 N2 2.082(2) . ?
Co1 N1 2.113(2) . ?
Co1 O1B 2.113(7) . ?
Co1 N4 2.115(3) . ?
Co1 O2B 2.149(7) . ?
Co1 O3A 2.152(4) 2_545 ?
Co1 O2A 2.286(3) . ?
Co1 O1A 2.287(4) . ?
Co1 C21B 2.478(9) . ?
N1 C5 1.338(4) . ?
N1 C1 1.351(3) . ?
N2 C7 1.310(3) . ?
N2 C6 1.467(3) . ?
N3 C7 1.361(3) . ?
N3 C15 1.450(4) . ?
N3 C14 1.455(4) . ?
N4 C16 1.348(5) . ?
N4 C20 1.348(5) . ?
C1 C2 1.371(5) . ?
C1 H1 0.95 . ?
C2 C3 1.394(5) . ?
C2 H2 0.95 . ?
C3 C4 1.378(4) . ?
C3 H3 0.95 . ?
C4 C5 1.391(4) . ?
C4 H4 0.95 . ?
C5 C6 1.515(4) . ?
C6 H6A 0.99 . ?
C6 H6B 0.99 . ?
C7 C8 1.486(4) . ?
C8 C9 1.395(4) . ?
C8 C13 1.396(4) . ?
C9 C10 1.385(4) . ?
C9 H9 0.95 . ?
C10 C11 1.387(4) . ?
C10 H10 0.95 . ?
C11 C12 1.371(5) . ?
C11 H11 0.95 . ?
C12 C13 1.383(4) . ?
C12 H12 0.95 . ?
C13 C14 1.486(4) . ?
C14 H14A 0.99 . ?
C14 H14B 0.99 . ?
C15 C16 1.500(5) . ?
C15 H15A 0.99 . ?
C15 H15B 0.99 . ?
C16 C17 1.391(5) . ?
C17 C18 1.382(7) . ?
C17 H17 0.95 . ?
C18 C19 1.370(7) . ?
C18 H18 0.95 . ?
C19 C20 1.387(5) . ?
C19 H19 0.95 . ?
C20 H20 0.95 . ?
O1A C21A 1.261(6) . ?
O2A C21A 1.261(5) . ?
O3A C24A 1.221(7) . ?
O3A Co1 2.152(4) 2 ?
O4A C24A 1.261(7) . ?
C21A C22A 1.523(7) . ?
C22A C23A 1.485(7) . ?
C22A H22A 0.99 . ?
C22A H22B 0.99 . ?
C23A C24A 1.529(6) . ?
C23A H23A 0.99 . ?
C23A H23B 0.99 . ?
O1B C21B 1.281(11) . ?
O2B C21B 1.285(11) . ?
O3B C24B 1.279(14) . ?
O3B Co1 1.833(7) 2 ?
O4B C24B 1.315(15) . ?
C21B C22B 1.504(11) . ?
C22B C23B 1.509(11) . ?
C22B H22C 0.99 . ?
C22B H22D 0.99 . ?
C23B C24B 1.546(12) . ?
C23B H23C 0.99 . ?
C23B H23D 0.99 . ?
O5 H5A 0.895(18) . ?
O5 H5B 0.874(17) . ?
O6A O6A 1.816(16) 3_476 ?

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
O3B Co1 N2 94.3(2) 2_545 . ?
O3B Co1 N1 96.4(2) 2_545 . ?
N2 Co1 N1 79.88(9) . . ?
O3B Co1 O1B 155.9(3) 2_545 . ?
N2 Co1 O1B 109.7(2) . . ?
N1 Co1 O1B 87.2(2) . . ?
O3B Co1 N4 82.3(3) 2_545 . ?
N2 Co1 N4 101.63(10) . . ?
N1 Co1 N4 178.10(11) . . ?
O1B Co1 N4 93.3(2) . . ?
O3B Co1 O2B 94.0(3) 2_545 . ?
N2 Co1 O2B 165.58(18) . . ?
N1 Co1 O2B 87.51(19) . . ?
O1B Co1 O2B 62.3(3) . . ?
N4 Co1 O2B 91.13(19) . . ?
N2 Co1 O3A 92.96(12) . 2_545 ?
N1 Co1 O3A 86.23(12) . 2_545 ?
N4 Co1 O3A 92.52(14) . 2_545 ?
N2 Co1 O2A 157.88(12) . . ?
N1 Co1 O2A 94.03(10) . . ?
N4 Co1 O2A 84.98(11) . . ?
O3A Co1 O2A 107.94(14) 2_545 . ?
N2 Co1 O1A 101.03(12) . . ?
N1 Co1 O1A 91.48(11) . . ?
N4 Co1 O1A 89.36(12) . . ?
O3A Co1 O1A 165.21(14) 2_545 . ?
O2A Co1 O1A 57.60(14) . . ?
O3B Co1 C21B 125.0(3) 2_545 . ?
N2 Co1 C21B 140.2(3) . . ?
N1 Co1 C21B 88.4(2) . . ?
O1B Co1 C21B 31.1(3) . . ?
N4 Co1 C21B 91.1(2) . . ?
O2B Co1 C21B 31.2(3) . . ?
C5 N1 C1 118.5(3) . . ?
C5 N1 Co1 111.43(17) . . ?
C1 N1 Co1 128.2(2) . . ?
C7 N2 C6 116.3(2) . . ?
C7 N2 Co1 129.30(18) . . ?
C6 N2 Co1 109.95(17) . . ?
C7 N3 C15 125.8(2) . . ?
C7 N3 C14 113.4(2) . . ?
C15 N3 C14 120.8(2) . . ?
C16 N4 C20 118.3(3) . . ?
C16 N4 Co1 123.0(2) . . ?
C20 N4 Co1 118.7(3) . . ?
N1 C1 C2 122.4(3) . . ?
N1 C1 H1 118.8 . . ?
C2 C1 H1 118.8 . . ?
C1 C2 C3 119.0(3) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C4 C3 C2 118.9(3) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C3 C4 C5 118.9(3) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
N1 C5 C4 122.2(3) . . ?
N1 C5 C6 117.9(2) . . ?
C4 C5 C6 120.0(3) . . ?
N2 C6 C5 111.8(2) . . ?
N2 C6 H6A 109.3 . . ?
C5 C6 H6A 109.3 . . ?
N2 C6 H6B 109.3 . . ?
C5 C6 H6B 109.3 . . ?
H6A C6 H6B 107.9 . . ?
N2 C7 N3 122.1(2) . . ?
N2 C7 C8 131.7(2) . . ?
N3 C7 C8 106.1(2) . . ?
C9 C8 C13 119.5(3) . . ?
C9 C8 C7 132.6(2) . . ?
C13 C8 C7 107.9(2) . . ?
C10 C9 C8 118.3(3) . . ?
C10 C9 H9 120.9 . . ?
C8 C9 H9 120.9 . . ?
C9 C10 C11 121.5(3) . . ?
C9 C10 H10 119.2 . . ?
C11 C10 H10 119.2 . . ?
C12 C11 C10 120.5(3) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 118.7(3) . . ?
C11 C12 H12 120.6 . . ?
C13 C12 H12 120.6 . . ?
C12 C13 C8 121.5(3) . . ?
C12 C13 C14 128.8(3) . . ?
C8 C13 C14 109.7(2) . . ?
N3 C14 C13 102.6(2) . . ?
N3 C14 H14A 111.2 . . ?
C13 C14 H14A 111.2 . . ?
N3 C14 H14B 111.2 . . ?
C13 C14 H14B 111.2 . . ?
H14A C14 H14B 109.2 . . ?
N3 C15 C16 112.0(3) . . ?
N3 C15 H15A 109.2 . . ?
C16 C15 H15A 109.2 . . ?
N3 C15 H15B 109.2 . . ?
C16 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
N4 C16 C17 121.9(4) . . ?
N4 C16 C15 115.7(3) . . ?
C17 C16 C15 122.4(4) . . ?
C18 C17 C16 119.0(5) . . ?
C18 C17 H17 120.5 . . ?
C16 C17 H17 120.5 . . ?
C19 C18 C17 119.3(4) . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C18 C19 C20 119.1(4) . . ?
C18 C19 H19 120.4 . . ?
C20 C19 H19 120.4 . . ?
N4 C20 C19 122.3(5) . . ?
N4 C20 H20 118.9 . . ?
C19 C20 H20 118.9 . . ?
C21A O1A Co1 90.3(3) . . ?
C21A O2A Co1 90.3(3) . . ?
C24A O3A Co1 137.6(3) . 2 ?
O2A C21A O1A 121.8(4) . . ?
O2A C21A C22A 121.9(4) . . ?
O1A C21A C22A 116.3(4) . . ?
C23A C22A C21A 119.2(5) . . ?
C23A C22A H22A 107.5 . . ?
C21A C22A H22A 107.5 . . ?
C23A C22A H22B 107.5 . . ?
C21A C22A H22B 107.5 . . ?
H22A C22A H22B 107 . . ?
C22A C23A C24A 114.2(5) . . ?
C22A C23A H23A 108.7 . . ?
C24A C23A H23A 108.7 . . ?
C22A C23A H23B 108.7 . . ?
C24A C23A H23B 108.7 . . ?
H23A C23A H23B 107.6 . . ?
O3A C24A O4A 123.0(5) . . ?
O3A C24A C23A 121.9(5) . . ?
O4A C24A C23A 115.1(5) . . ?
C21B O1B Co1 90.4(6) . . ?
C21B O2B Co1 88.7(5) . . ?
C24B O3B Co1 131.7(7) . 2 ?
O1B C21B O2B 118.4(8) . . ?
O1B C21B C22B 124.3(9) . . ?
O2B C21B C22B 116.9(8) . . ?
O1B C21B Co1 58.5(5) . . ?
O2B C21B Co1 60.1(4) . . ?
C22B C21B Co1 176.1(7) . . ?
C21B C22B C23B 113.4(8) . . ?
C21B C22B H22C 108.9 . . ?
C23B C22B H22C 108.9 . . ?
C21B C22B H22D 108.9 . . ?
C23B C22B H22D 108.9 . . ?
H22C C22B H22D 107.7 . . ?
C22B C23B C24B 114.5(8) . . ?
C22B C23B H23C 108.6 . . ?
C24B C23B H23C 108.6 . . ?
C22B C23B H23D 108.6 . . ?
C24B C23B H23D 108.6 . . ?
H23C C23B H23D 107.6 . . ?
O3B C24B O4B 130.7(10) . . ?
O3B C24B C23B 114.6(9) . . ?
O4B C24B C23B 114.7(10) . . ?
H5A O5 H5B 101(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 2.7(4) . . . . ?
Co1 N1 C1 C2 -160.4(2) . . . . ?
N1 C1 C2 C3 0.6(5) . . . . ?
C1 C2 C3 C4 -2.4(5) . . . . ?
C2 C3 C4 C5 1.1(5) . . . . ?
C1 N1 C5 C4 -4.1(4) . . . . ?
Co1 N1 C5 C4 161.7(2) . . . . ?
C1 N1 C5 C6 177.2(2) . . . . ?
Co1 N1 C5 C6 -17.1(3) . . . . ?
C3 C4 C5 N1 2.2(4) . . . . ?
C3 C4 C5 C6 -179.1(3) . . . . ?
C7 N2 C6 C5 -176.4(2) . . . . ?
Co1 N2 C6 C5 25.0(3) . . . . ?
N1 C5 C6 N2 -5.3(3) . . . . ?
C4 C5 C6 N2 175.9(2) . . . . ?
C6 N2 C7 N3 175.9(2) . . . . ?
Co1 N2 C7 N3 -30.4(4) . . . . ?
C6 N2 C7 C8 -6.0(4) . . . . ?
Co1 N2 C7 C8 147.7(2) . . . . ?
C15 N3 C7 N2 -7.6(4) . . . . ?
C14 N3 C7 N2 173.5(3) . . . . ?
C15 N3 C7 C8 174.0(3) . . . . ?
C14 N3 C7 C8 -4.9(3) . . . . ?
N2 C7 C8 C9 4.7(5) . . . . ?
N3 C7 C8 C9 -177.0(3) . . . . ?
N2 C7 C8 C13 -173.5(3) . . . . ?
N3 C7 C8 C13 4.8(3) . . . . ?
C13 C8 C9 C10 1.5(4) . . . . ?
C7 C8 C9 C10 -176.6(3) . . . . ?
C8 C9 C10 C11 0.6(4) . . . . ?
C9 C10 C11 C12 -1.6(5) . . . . ?
C10 C11 C12 C13 0.6(5) . . . . ?
C11 C12 C13 C8 1.5(4) . . . . ?
C11 C12 C13 C14 -179.9(3) . . . . ?
C9 C8 C13 C12 -2.5(4) . . . . ?
C7 C8 C13 C12 175.9(3) . . . . ?
C9 C8 C13 C14 178.6(3) . . . . ?
C7 C8 C13 C14 -2.9(3) . . . . ?
C7 N3 C14 C13 3.1(3) . . . . ?
C15 N3 C14 C13 -175.8(3) . . . . ?
C12 C13 C14 N3 -178.7(3) . . . . ?
C8 C13 C14 N3 0.1(3) . . . . ?
C7 N3 C15 C16 92.0(4) . . . . ?
C14 N3 C15 C16 -89.1(4) . . . . ?
C20 N4 C16 C17 1.7(5) . . . . ?
Co1 N4 C16 C17 -177.2(2) . . . . ?
C20 N4 C16 C15 178.3(3) . . . . ?
Co1 N4 C16 C15 -0.7(4) . . . . ?
N3 C15 C16 N4 -80.4(3) . . . . ?
N3 C15 C16 C17 96.1(4) . . . . ?
N4 C16 C17 C18 0.4(5) . . . . ?
C15 C16 C17 C18 -175.9(3) . . . . ?
C16 C17 C18 C19 -1.9(6) . . . . ?
C17 C18 C19 C20 1.3(6) . . . . ?
C16 N4 C20 C19 -2.4(5) . . . . ?
Co1 N4 C20 C19 176.6(3) . . . . ?
C18 C19 C20 N4 0.9(6) . . . . ?
Co1 O2A C21A O1A -1.7(5) . . . . ?
Co1 O2A C21A C22A -178.6(4) . . . . ?
Co1 O1A C21A O2A 1.7(5) . . . . ?
Co1 O1A C21A C22A 178.8(4) . . . . ?
O2A C21A C22A C23A -4.4(8) . . . . ?
O1A C21A C22A C23A 178.5(5) . . . . ?
C21A C22A C23A C24A 174.0(4) . . . . ?
Co1 O3A C24A O4A 113.4(6) 2 . . . ?
Co1 O3A C24A C23A -65.2(8) 2 . . . ?
C22A C23A C24A O3A -20.9(7) . . . . ?
C22A C23A C24A O4A 160.4(5) . . . . ?
Co1 O1B C21B O2B -4.7(9) . . . . ?
Co1 O1B C21B C22B -176.8(9) . . . . ?
Co1 O2B C21B O1B 4.6(9) . . . . ?
Co1 O2B C21B C22B 177.3(8) . . . . ?
O1B C21B C22B C23B -26.6(14) . . . . ?
O2B C21B C22B C23B 161.2(8) . . . . ?
C21B C22B C23B C24B -169.5(8) . . . . ?
Co1 O3B C24B O4B 128.1(11) 2 . . . ?
Co1 O3B C24B C23B -51.1(13) 2 . . . ?
C22B C23B C24B O3B 159.6(9) . . . . ?
C22B C23B C24B O4B -19.8(13) . . . . ?

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
C15 H15A O1B 0.99 2.61 3.460(8) 144.5 .
C23B H23D O2B 0.99 1.93 2.779(12) 142.6 2
C1 H1 O2B 0.95 2.55 3.054(7) 113.1 .
C4 H4 O5 0.95 2.55 3.454(4) 158.2 4_575
C14 H14A O7 0.99 2.6 3.412(5) 139.8 4_685
C14 H14B O6B 0.99 2.56 3.431(8) 147.1 2
C14 H14B O6A 0.99 2.46 3.337(8) 147 2
C15 H15A O1A 0.99 2.29 3.182(5) 149.9 .
C15 H15A O1B 0.99 2.61 3.460(8) 144.5 .
C19 H19 O7 0.95 2.54 3.144(7) 121.4 3_576
C22A H22A O2A 0.99 2.61 3.587(8) 169.4 2
C23B H23D O2B 0.99 1.93 2.779(12) 142.6 2
O5 H5A O2A 0.895(18) 2.04(2) 2.933(5) 172(4) .
O5 H5A O2B 0.895(18) 1.94(3) 2.782(7) 156(4) .
O5 H5B O1A 0.874(17) 1.821(18) 2.694(5) 178(3) 2_545
O5 H5B O1B 0.874(17) 2.21(2) 3.075(8) 172(3) 2_545


_shelxl_version_number           2012-9




# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
_exptl_crystal_preparation       'Magnetic properties, Luminescent'
