# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_complex1
_database_code_depnum_ccdc_archive 'CCDC 1456816'
_audit_update_record             
;
2016-03-01 deposited with the CCDC.
2016-05-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C44 H64 Cl2 Co N4 O5'
_chemical_formula_weight         858.82

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2/c

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

_cell_length_a                   14.2041(6)
_cell_length_b                   10.6502(4)
_cell_length_c                   16.5585(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.337(4)
_cell_angle_gamma                90.00
_cell_volume                     2494.05(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    10168
_cell_measurement_theta_min      2.9
_cell_measurement_theta_max      25

_exptl_crystal_description       plate
_exptl_crystal_colour            pink
_exptl_crystal_size_max          1
_exptl_crystal_size_mid          .08
_exptl_crystal_size_min          .05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.144
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             914
_exptl_absorpt_coefficient_mu    0.493
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.78924
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'face installed'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10168
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_sigmaI/netI    0.0448
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.88
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4396
_reflns_number_gt                3371
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_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)+(0.1190P)²+1.2704P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4396
_refine_ls_number_parameters     261
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0832
_refine_ls_R_factor_gt           0.0654
_refine_ls_wR_factor_ref         0.2232
_refine_ls_wR_factor_gt          0.2062
_refine_ls_goodness_of_fit_ref   1.154
_refine_ls_restrained_S_all      1.154
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.5000 1.0000 0.0000 0.0399(3) Uani 1 2 d S . .
Cl1 Cl 0.52590(9) 0.83282(10) -0.09796(6) 0.0586(4) Uani 1 1 d . . .
N2 N 0.5552(2) 0.8764(3) 0.10725(19) 0.0427(8) Uani 1 1 d . . .
H2N H 0.5865 0.9279 0.1445 0.051 Uiso 1 1 calc R . .
N1 N 0.3679(2) 0.9190(3) 0.02710(19) 0.0440(8) Uani 1 1 d . . .
H1N H 0.3436 0.9735 0.0620 0.053 Uiso 1 1 calc R . .
C15 C 0.7227(3) 0.7232(4) 0.2230(3) 0.0504(10) Uani 1 1 d . . .
C14 C 0.6506(3) 0.6865(4) 0.1637(2) 0.0472(10) Uani 1 1 d . . .
C13 C 0.6205(3) 0.7715(4) 0.0926(2) 0.0472(9) Uani 1 1 d . . .
H13A H 0.6770 0.8071 0.0732 0.057 Uiso 1 1 calc R . .
H13B H 0.5905 0.7199 0.0494 0.057 Uiso 1 1 calc R . .
C11 C 0.3922(3) 0.8040(4) 0.0752(3) 0.0502(10) Uani 1 1 d . . .
H11A H 0.4145 0.7394 0.0403 0.060 Uiso 1 1 calc R . .
H11B H 0.3365 0.7726 0.0983 0.060 Uiso 1 1 calc R . .
C19 C 0.6095(3) 0.5678(4) 0.1705(3) 0.0569(11) Uani 1 1 d . . .
C5 C 0.2007(3) 0.8451(4) -0.0085(3) 0.0504(10) Uani 1 1 d . . .
C10 C 0.2912(3) 0.8969(5) -0.0382(3) 0.0551(11) Uani 1 1 d . . .
H10A H 0.3137 0.8385 -0.0770 0.066 Uiso 1 1 calc R . .
H10B H 0.2768 0.9755 -0.0663 0.066 Uiso 1 1 calc R . .
C4 C 0.1450(3) 0.9207(4) 0.0368(3) 0.0583(11) Uani 1 1 d . . .
C16 C 0.7513(3) 0.6422(5) 0.2861(3) 0.0609(12) Uani 1 1 d . . .
H16 H 0.7997 0.6673 0.3244 0.073 Uiso 1 1 calc R . .
C6 C 0.1733(3) 0.7203(5) -0.0253(3) 0.0643(12) Uani 1 1 d . . .
C12 C 0.4682(3) 0.8347(4) 0.1420(2) 0.0459(9) Uani 1 1 d . . .
H12A H 0.4461 0.9005 0.1761 0.055 Uiso 1 1 calc R . .
H12B H 0.4818 0.7610 0.1755 0.055 Uiso 1 1 calc R . .
C17 C 0.7108(4) 0.5259(5) 0.2941(3) 0.0687(14) Uani 1 1 d . . .
C20 C 0.5349(4) 0.5176(4) 0.1089(4) 0.0775(16) Uani 1 1 d . . .
H20B H 0.4770 0.5629 0.1125 0.116 Uiso 1 1 calc R . .
H20A H 0.5248 0.4301 0.1192 0.116 Uiso 1 1 calc R . .
H20C H 0.5551 0.5275 0.0555 0.116 Uiso 1 1 calc R . .
C18 C 0.6395(4) 0.4895(4) 0.2350(3) 0.0692(14) Uani 1 1 d . . .
H18 H 0.6114 0.4111 0.2388 0.083 Uiso 1 1 calc R . .
C21 C 0.7705(3) 0.8489(5) 0.2209(3) 0.0684(13) Uani 1 1 d . . .
H21C H 0.8222 0.8523 0.2625 0.103 Uiso 1 1 calc R . .
H21A H 0.7259 0.9140 0.2298 0.103 Uiso 1 1 calc R . .
H21B H 0.7940 0.8607 0.1689 0.103 Uiso 1 1 calc R . .
C2 C 0.0367(3) 0.7459(5) 0.0514(4) 0.0743(14) Uani 1 1 d . . .
C3 C 0.0646(3) 0.8699(5) 0.0654(4) 0.0731(14) Uani 1 1 d . . .
H3 H 0.0275 0.9210 0.0952 0.088 Uiso 1 1 calc R . .
C8 C 0.1690(4) 1.0547(5) 0.0561(4) 0.0875(18) Uani 1 1 d . . .
H8B H 0.1980 1.0917 0.0117 0.131 Uiso 1 1 calc R . .
H8C H 0.2120 1.0586 0.1043 0.131 Uiso 1 1 calc R . .
H8A H 0.1123 1.0999 0.0647 0.131 Uiso 1 1 calc R . .
C7 C 0.0914(3) 0.6754(5) 0.0054(4) 0.0744(15) Uani 1 1 d . . .
H7 H 0.0731 0.5930 -0.0063 0.089 Uiso 1 1 calc R . .
C9 C 0.2299(4) 0.6331(6) -0.0739(4) 0.098(2) Uani 1 1 d . . .
H9A H 0.1931 0.5596 -0.0887 0.147 Uiso 1 1 calc R . .
H9B H 0.2869 0.6090 -0.0419 0.147 Uiso 1 1 calc R . .
H9C H 0.2457 0.6751 -0.1221 0.147 Uiso 1 1 calc R . .
C1 C -0.0508(5) 0.6935(7) 0.0857(6) 0.121(3) Uani 1 1 d . . .
H1A H -0.0437 0.6045 0.0934 0.181 Uiso 1 1 calc R . .
H1B H -0.1054 0.7099 0.0486 0.181 Uiso 1 1 calc R . .
H1C H -0.0585 0.7329 0.1368 0.181 Uiso 1 1 calc R . .
C22 C 0.7415(5) 0.4400(7) 0.3639(4) 0.105(2) Uani 1 1 d . . .
H22A H 0.7723 0.4883 0.4076 0.157 Uiso 1 1 calc R . .
H22B H 0.7845 0.3783 0.3466 0.157 Uiso 1 1 calc R . .
H22C H 0.6871 0.3988 0.3820 0.157 Uiso 1 1 calc R . .
O1 O 0.3672(3) 0.1124(4) 0.2586(3) 0.0935(12) Uani 1 1 d . . .
O3 O 0.0000 0.3747(7) 0.2500 0.140(3) Uani 1 2 d S . .
O2 O 0.1013(6) 0.1490(7) 0.2650(3) 0.205(4) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 N1 2.150(3) . ?
Co1 N1 2.150(3) 3_675 ?
Co1 N2 2.289(3) 3_675 ?
Co1 N2 2.289(3) . ?
Co1 Cl1 2.4592(10) 3_675 ?
Co1 Cl1 2.4592(10) . ?
N2 C12 1.480(5) . ?
N2 C13 1.486(5) . ?
N2 H2N 0.9100 . ?
N1 C10 1.481(5) . ?
N1 C11 1.484(5) . ?
N1 H1N 0.9100 . ?
C15 C16 1.387(6) . ?
C15 C14 1.406(6) . ?
C15 C21 1.503(6) . ?
C14 C19 1.401(6) . ?
C14 C13 1.514(6) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C11 C12 1.508(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C19 C18 1.390(7) . ?
C19 C20 1.500(7) . ?
C5 C4 1.395(6) . ?
C5 C6 1.405(6) . ?
C5 C10 1.522(6) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C4 C3 1.387(7) . ?
C4 C8 1.495(7) . ?
C16 C17 1.378(7) . ?
C16 H16 0.9300 . ?
C6 C7 1.397(7) . ?
C6 C9 1.510(7) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C17 C18 1.396(8) . ?
C17 C22 1.506(7) . ?
C20 H20B 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20C 0.9600 . ?
C18 H18 0.9300 . ?
C21 H21C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C2 C7 1.364(8) . ?
C2 C3 1.392(7) . ?
C2 C1 1.519(8) . ?
C3 H3 0.9300 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C8 H8A 0.9600 . ?
C7 H7 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Co1 N1 180.0 . 3_675 ?
N1 Co1 N2 98.63(11) . 3_675 ?
N1 Co1 N2 81.37(11) 3_675 3_675 ?
N1 Co1 N2 81.38(11) . . ?
N1 Co1 N2 98.63(11) 3_675 . ?
N2 Co1 N2 180.0 3_675 . ?
N1 Co1 Cl1 88.04(10) . 3_675 ?
N1 Co1 Cl1 91.96(10) 3_675 3_675 ?
N2 Co1 Cl1 91.95(8) 3_675 3_675 ?
N2 Co1 Cl1 88.05(8) . 3_675 ?
N1 Co1 Cl1 91.96(10) . . ?
N1 Co1 Cl1 88.04(10) 3_675 . ?
N2 Co1 Cl1 88.05(8) 3_675 . ?
N2 Co1 Cl1 91.95(8) . . ?
Cl1 Co1 Cl1 180.0 3_675 . ?
C12 N2 C13 113.2(3) . . ?
C12 N2 Co1 103.7(2) . . ?
C13 N2 Co1 118.7(2) . . ?
C12 N2 H2N 106.9 . . ?
C13 N2 H2N 106.9 . . ?
Co1 N2 H2N 106.9 . . ?
C10 N1 C11 112.3(3) . . ?
C10 N1 Co1 120.6(2) . . ?
C11 N1 Co1 106.2(2) . . ?
C10 N1 H1N 105.5 . . ?
C11 N1 H1N 105.5 . . ?
Co1 N1 H1N 105.5 . . ?
C16 C15 C14 119.8(4) . . ?
C16 C15 C21 118.1(4) . . ?
C14 C15 C21 122.2(4) . . ?
C19 C14 C15 118.5(4) . . ?
C19 C14 C13 120.8(4) . . ?
C15 C14 C13 120.7(4) . . ?
N2 C13 C14 117.3(3) . . ?
N2 C13 H13A 108.0 . . ?
C14 C13 H13A 108.0 . . ?
N2 C13 H13B 108.0 . . ?
C14 C13 H13B 108.0 . . ?
H13A C13 H13B 107.2 . . ?
N1 C11 C12 109.2(3) . . ?
N1 C11 H11A 109.8 . . ?
C12 C11 H11A 109.8 . . ?
N1 C11 H11B 109.8 . . ?
C12 C11 H11B 109.8 . . ?
H11A C11 H11B 108.3 . . ?
C18 C19 C14 120.2(4) . . ?
C18 C19 C20 117.1(4) . . ?
C14 C19 C20 122.7(4) . . ?
C4 C5 C6 119.5(4) . . ?
C4 C5 C10 120.2(4) . . ?
C6 C5 C10 120.4(4) . . ?
N1 C10 C5 114.1(3) . . ?
N1 C10 H10A 108.7 . . ?
C5 C10 H10A 108.7 . . ?
N1 C10 H10B 108.7 . . ?
C5 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C3 C4 C5 119.0(4) . . ?
C3 C4 C8 118.5(5) . . ?
C5 C4 C8 122.5(4) . . ?
C17 C16 C15 122.4(4) . . ?
C17 C16 H16 118.8 . . ?
C15 C16 H16 118.8 . . ?
C7 C6 C5 118.5(5) . . ?
C7 C6 C9 119.1(5) . . ?
C5 C6 C9 122.5(4) . . ?
N2 C12 C11 110.3(3) . . ?
N2 C12 H12A 109.6 . . ?
C11 C12 H12A 109.6 . . ?
N2 C12 H12B 109.6 . . ?
C11 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
C16 C17 C18 117.7(4) . . ?
C16 C17 C22 121.7(5) . . ?
C18 C17 C22 120.6(5) . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20A 109.5 . . ?
H20B C20 H20A 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
C19 C18 C17 121.5(5) . . ?
C19 C18 H18 119.3 . . ?
C17 C18 H18 119.3 . . ?
C15 C21 H21C 109.5 . . ?
C15 C21 H21A 109.5 . . ?
H21C C21 H21A 109.5 . . ?
C15 C21 H21B 109.5 . . ?
H21C C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C7 C2 C3 116.6(5) . . ?
C7 C2 C1 122.3(5) . . ?
C3 C2 C1 121.1(6) . . ?
C4 C3 C2 123.0(5) . . ?
C4 C3 H3 118.5 . . ?
C2 C3 H3 118.5 . . ?
C4 C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C4 C8 H8A 109.5 . . ?
H8B C8 H8A 109.5 . . ?
H8C C8 H8A 109.5 . . ?
C2 C7 C6 123.5(5) . . ?
C2 C7 H7 118.3 . . ?
C6 C7 H7 118.3 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C17 C22 H22A 109.5 . . ?
C17 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C17 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.185
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.101
####################################################################### 
# 
# 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_complex2
_database_code_depnum_ccdc_archive 'CCDC 1456817'
_audit_update_record             
;
2016-03-01 deposited with the CCDC.
2016-05-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H39 Cl2 Co N3 O2'
_chemical_formula_weight         531.41

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   p212121

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

_cell_length_a                   27.9485(17)
_cell_length_b                   11.5046(5)
_cell_length_c                   8.5689(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2755.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7700
_cell_measurement_theta_min      3
_cell_measurement_theta_max      25.3

_exptl_crystal_description       block
_exptl_crystal_colour            pink
_exptl_crystal_size_max          .80
_exptl_crystal_size_mid          .65
_exptl_crystal_size_min          .41
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1124
_exptl_absorpt_coefficient_mu    0.841
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.30396
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'face installed'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7700
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_sigmaI/netI    0.0613
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.96
_diffrn_reflns_theta_max         25.25
_reflns_number_total             4668
_reflns_number_gt                3614
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(3)
_refine_ls_number_reflns         4668
_refine_ls_number_parameters     296
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0782
_refine_ls_R_factor_gt           0.0581
_refine_ls_wR_factor_ref         0.1795
_refine_ls_wR_factor_gt          0.1596
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.26689(3) 0.70402(6) 0.69355(9) 0.0419(2) Uani 1 1 d . . .
Cl2 Cl 0.23850(6) 0.50189(11) 0.70559(18) 0.0527(4) Uani 1 1 d . . .
Cl1 Cl 0.30217(7) 0.91611(14) 0.6668(2) 0.0660(5) Uani 1 1 d . . .
O1 O 0.25981(18) 0.6986(4) 0.4572(4) 0.0607(12) Uani 1 1 d . . .
H0AA H 0.2853 0.6613 0.4042 0.091 Uiso 1 1 d R . .
H0AB H 0.2578 0.7721 0.4071 0.091 Uiso 1 1 d R . .
N3 N 0.34168(17) 0.6617(4) 0.7142(6) 0.0493(12) Uani 1 1 d . . .
H0AC H 0.3576 0.7288 0.6926 0.059 Uiso 1 1 calc R . .
C11 C 0.1911(2) 0.7684(6) 0.9194(7) 0.0512(16) Uani 1 1 d . . .
H11A H 0.1787 0.6906 0.9360 0.061 Uiso 1 1 calc R . .
H11B H 0.1677 0.8236 0.9580 0.061 Uiso 1 1 calc R . .
N1 N 0.19960(18) 0.7881(4) 0.7498(5) 0.0468(11) Uani 1 1 d . . .
H1 H 0.2048 0.8657 0.7387 0.056 Uiso 1 1 calc R . .
N2 N 0.27241(17) 0.7017(4) 0.9405(5) 0.0440(11) Uani 1 1 d . . .
H1AC H 0.2638 0.6293 0.9725 0.053 Uiso 1 1 calc R . .
C12 C 0.2374(2) 0.7831(5) 1.0055(7) 0.0516(15) Uani 1 1 d . . .
H12A H 0.2489 0.8622 0.9943 0.062 Uiso 1 1 calc R . .
H12B H 0.2327 0.7675 1.1157 0.062 Uiso 1 1 calc R . .
C13 C 0.3228(2) 0.7176(6) 0.9837(7) 0.0569(16) Uani 1 1 d . . .
H13A H 0.3274 0.6994 1.0932 0.068 Uiso 1 1 calc R . .
H13B H 0.3325 0.7975 0.9659 0.068 Uiso 1 1 calc R . .
C5 C 0.1097(2) 0.7727(5) 0.7174(8) 0.0547(16) Uani 1 1 d . . .
C6 C 0.0828(2) 0.6742(6) 0.7601(8) 0.0583(18) Uani 1 1 d . . .
C9 C 0.0988(3) 0.5508(6) 0.7190(10) 0.072(2) Uani 1 1 d . . .
H9A H 0.0999 0.5422 0.6076 0.108 Uiso 1 1 calc R . .
H9B H 0.0766 0.4958 0.7619 0.108 Uiso 1 1 calc R . .
H9C H 0.1301 0.5369 0.7616 0.108 Uiso 1 1 calc R . .
C16 C 0.4152(2) 0.5532(6) 0.6246(8) 0.0542(16) Uani 1 1 d . . .
C21 C 0.4326(2) 0.4560(6) 0.6996(10) 0.0630(17) Uani 1 1 d . . .
C4 C 0.0907(3) 0.8839(6) 0.7566(10) 0.067(2) Uani 1 1 d . . .
C7 C 0.0392(2) 0.6862(7) 0.8363(8) 0.0664(19) Uani 1 1 d . . .
H7 H 0.0218 0.6199 0.8619 0.080 Uiso 1 1 calc R . .
C15 C 0.3619(2) 0.5738(6) 0.6077(8) 0.0584(17) Uani 1 1 d . . .
H15A H 0.3555 0.5977 0.5012 0.070 Uiso 1 1 calc R . .
H15B H 0.3454 0.5008 0.6250 0.070 Uiso 1 1 calc R . .
C10 C 0.1580(2) 0.7597(5) 0.6475(7) 0.0527(16) Uani 1 1 d . . .
H10A H 0.1596 0.8090 0.5558 0.063 Uiso 1 1 calc R . .
H10B H 0.1614 0.6800 0.6125 0.063 Uiso 1 1 calc R . .
C17 C 0.4480(3) 0.6347(7) 0.5633(9) 0.0633(18) Uani 1 1 d . . .
C3 C 0.0468(3) 0.8895(8) 0.8321(11) 0.083(3) Uani 1 1 d . . .
H3 H 0.0344 0.9626 0.8546 0.099 Uiso 1 1 calc R . .
C20 C 0.4819(3) 0.4460(7) 0.7228(9) 0.068(2) Uani 1 1 d . . .
H20 H 0.4934 0.3824 0.7785 0.081 Uiso 1 1 calc R . .
C19 C 0.5143(3) 0.5258(8) 0.6670(10) 0.072(2) Uani 1 1 d . . .
C1 C -0.0255(3) 0.8017(10) 0.9649(10) 0.100(3) Uani 1 1 d . . .
H1A H -0.0502 0.8312 0.8978 0.149 Uiso 1 1 calc R . .
H1B H -0.0215 0.8530 1.0523 0.149 Uiso 1 1 calc R . .
H1C H -0.0343 0.7259 1.0016 0.149 Uiso 1 1 calc R . .
C18 C 0.4965(3) 0.6195(8) 0.5854(9) 0.069(2) Uani 1 1 d . . .
H18 H 0.5177 0.6739 0.5443 0.083 Uiso 1 1 calc R . .
C24 C 0.5679(3) 0.5135(10) 0.6964(14) 0.110(3) Uani 1 1 d . . .
H24A H 0.5760 0.5500 0.7937 0.165 Uiso 1 1 calc R . .
H24B H 0.5853 0.5501 0.6132 0.165 Uiso 1 1 calc R . .
H24C H 0.5762 0.4326 0.7008 0.165 Uiso 1 1 calc R . .
C14 C 0.3517(2) 0.6368(7) 0.8836(8) 0.0583(18) Uani 1 1 d . . .
H14A H 0.3434 0.5568 0.9073 0.070 Uiso 1 1 calc R . .
H14B H 0.3855 0.6474 0.9050 0.070 Uiso 1 1 calc R . .
C2 C 0.0209(3) 0.7941(10) 0.8753(9) 0.079(2) Uani 1 1 d . . .
C8 C 0.1173(4) 0.9922(6) 0.7167(14) 0.104(3) Uani 1 1 d . . .
H8A H 0.1343 0.9811 0.6205 0.156 Uiso 1 1 calc R . .
H8B H 0.1396 1.0099 0.7985 0.156 Uiso 1 1 calc R . .
H8C H 0.0950 1.0553 0.7054 0.156 Uiso 1 1 calc R . .
C22 C 0.4010(3) 0.3567(7) 0.7565(11) 0.083(2) Uani 1 1 d . . .
H22A H 0.3694 0.3857 0.7776 0.124 Uiso 1 1 calc R . .
H22B H 0.4143 0.3243 0.8502 0.124 Uiso 1 1 calc R . .
H22C H 0.3993 0.2976 0.6776 0.124 Uiso 1 1 calc R . .
C23 C 0.4308(3) 0.7388(7) 0.4741(10) 0.083(2) Uani 1 1 d . . .
H23A H 0.4175 0.7945 0.5452 0.125 Uiso 1 1 calc R . .
H23B H 0.4067 0.7152 0.4006 0.125 Uiso 1 1 calc R . .
H23C H 0.4572 0.7732 0.4192 0.125 Uiso 1 1 calc R . .
O2 O 0.2678(4) 0.9102(5) 0.3282(10) 0.175(5) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 O1 2.036(4) . ?
Co1 N2 2.122(5) . ?
Co1 N3 2.153(5) . ?
Co1 N1 2.169(5) . ?
Co1 Cl2 2.4593(16) . ?
Co1 Cl1 2.6417(17) . ?
N3 C15 1.476(8) . ?
N3 C14 1.506(8) . ?
C11 N1 1.490(7) . ?
C11 C12 1.499(9) . ?
N1 C10 1.494(7) . ?
N2 C12 1.464(8) . ?
N2 C13 1.467(8) . ?
C13 C14 1.501(9) . ?
C5 C6 1.409(9) . ?
C5 C4 1.424(9) . ?
C5 C10 1.484(9) . ?
C6 C7 1.389(9) . ?
C6 C9 1.530(10) . ?
C16 C21 1.378(10) . ?
C16 C17 1.412(10) . ?
C16 C15 1.516(9) . ?
C21 C20 1.397(9) . ?
C21 C22 1.524(11) . ?
C4 C3 1.387(12) . ?
C4 C8 1.490(11) . ?
C7 C2 1.383(12) . ?
C17 C18 1.380(10) . ?
C17 C23 1.499(11) . ?
C3 C2 1.368(13) . ?
C20 C19 1.375(11) . ?
C19 C18 1.379(11) . ?
C19 C24 1.525(11) . ?
C1 C2 1.509(11) . ?

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 177.14(18) . . ?
O1 Co1 N3 99.7(2) . . ?
N2 Co1 N3 81.05(19) . . ?
O1 Co1 N1 98.67(19) . . ?
N2 Co1 N1 81.19(17) . . ?
N3 Co1 N1 157.52(18) . . ?
O1 Co1 Cl2 88.92(13) . . ?
N2 Co1 Cl2 88.27(15) . . ?
N3 Co1 Cl2 95.52(14) . . ?
N1 Co1 Cl2 97.61(14) . . ?
O1 Co1 Cl1 88.76(13) . . ?
N2 Co1 Cl1 94.07(15) . . ?
N3 Co1 Cl1 81.58(15) . . ?
N1 Co1 Cl1 86.05(14) . . ?
Cl2 Co1 Cl1 175.93(7) . . ?
C15 N3 C14 113.2(5) . . ?
C15 N3 Co1 118.4(4) . . ?
C14 N3 Co1 107.6(4) . . ?
N1 C11 C12 109.0(5) . . ?
C11 N1 C10 114.5(5) . . ?
C11 N1 Co1 106.7(4) . . ?
C10 N1 Co1 116.6(4) . . ?
C12 N2 C13 117.7(5) . . ?
C12 N2 Co1 108.9(3) . . ?
C13 N2 Co1 108.7(4) . . ?
N2 C12 C11 108.5(5) . . ?
N2 C13 C14 107.2(5) . . ?
C6 C5 C4 117.5(6) . . ?
C6 C5 C10 120.6(6) . . ?
C4 C5 C10 121.6(6) . . ?
C7 C6 C5 120.7(7) . . ?
C7 C6 C9 117.3(7) . . ?
C5 C6 C9 122.0(6) . . ?
C21 C16 C17 119.0(6) . . ?
C21 C16 C15 121.2(6) . . ?
C17 C16 C15 119.8(6) . . ?
C16 C21 C20 118.7(7) . . ?
C16 C21 C22 123.6(7) . . ?
C20 C21 C22 117.7(7) . . ?
C3 C4 C5 118.8(7) . . ?
C3 C4 C8 120.5(8) . . ?
C5 C4 C8 120.7(7) . . ?
C2 C7 C6 121.8(8) . . ?
N3 C15 C16 115.1(5) . . ?
C5 C10 N1 116.7(5) . . ?
C18 C17 C16 120.1(7) . . ?
C18 C17 C23 119.1(7) . . ?
C16 C17 C23 120.8(7) . . ?
C2 C3 C4 123.9(7) . . ?
C19 C20 C21 123.0(7) . . ?
C20 C19 C18 117.5(7) . . ?
C20 C19 C24 121.8(8) . . ?
C18 C19 C24 120.7(8) . . ?
C19 C18 C17 121.6(7) . . ?
C13 C14 N3 109.4(5) . . ?
C3 C2 C7 117.3(7) . . ?
C3 C2 C1 123.1(9) . . ?
C7 C2 C1 119.5(9) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.677
_refine_diff_density_min         -0.690
_refine_diff_density_rms         0.069
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_complex3
_database_code_depnum_ccdc_archive 'CCDC 1456818'
_audit_update_record             
;
2016-03-01 deposited with the CCDC.
2016-05-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H54 Cl2 Co N4 O'
_chemical_formula_weight         688.66

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n

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

_cell_length_a                   14.6745(9)
_cell_length_b                   15.5490(9)
_cell_length_c                   17.1120(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.099(7)
_cell_angle_gamma                90.00
_cell_volume                     3769.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    15315
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      25.3

_exptl_crystal_description       block
_exptl_crystal_colour            pink
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1468
_exptl_absorpt_coefficient_mu    0.629
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.73228
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'face installed'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15315
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_sigmaI/netI    0.0383
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.99
_diffrn_reflns_theta_max         25.25
_reflns_number_total             6824
_reflns_number_gt                4912
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_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)+(0.0000P)²+1.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6824
_refine_ls_number_parameters     406
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0430
_refine_ls_wR_factor_ref         0.0669
_refine_ls_wR_factor_gt          0.0617
_refine_ls_goodness_of_fit_ref   1.296
_refine_ls_restrained_S_all      1.296
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.67929(2) 0.75222(2) 0.329917(19) 0.04436(10) Uani 1 1 d . . .
Cl2 Cl 0.74619(5) 0.52918(4) 0.26895(4) 0.0667(2) Uani 1 1 d . . .
Cl1 Cl 0.52220(5) 0.71345(5) 0.30366(4) 0.0674(2) Uani 1 1 d . . .
N4 N 0.83280(13) 0.78043(12) 0.36216(12) 0.0451(5) Uani 1 1 d . . .
N3 N 0.70134(13) 0.74072(12) 0.21504(11) 0.0465(5) Uani 1 1 d . . .
H3 H 0.7043 0.6833 0.2057 0.056 Uiso 1 1 calc R . .
N2 N 0.67650(13) 0.88391(12) 0.36113(12) 0.0474(5) Uani 1 1 d . . .
H2 H 0.6693 0.9144 0.3145 0.057 Uiso 1 1 calc R . .
N1 N 0.72847(13) 0.65948(12) 0.41992(11) 0.0451(5) Uani 1 1 d . . .
H1 H 0.7044 0.6085 0.3977 0.054 Uiso 1 1 calc R . .
C5 C 0.70022(17) 0.60460(15) 0.55236(14) 0.0448(6) Uani 1 1 d . . .
C4 C 0.65302(17) 0.52652(17) 0.53279(15) 0.0497(6) Uani 1 1 d . . .
C27 C 0.62244(17) 0.77490(16) 0.14827(14) 0.0532(7) Uani 1 1 d . . .
H27A H 0.6217 0.8371 0.1527 0.064 Uiso 1 1 calc R . .
H27B H 0.5633 0.7536 0.1560 0.064 Uiso 1 1 calc R . .
C11 C 0.83206(17) 0.64911(17) 0.44151(16) 0.0590(7) Uani 1 1 d . . .
H11A H 0.8494 0.6089 0.4045 0.071 Uiso 1 1 calc R . .
H11B H 0.8534 0.6258 0.4958 0.071 Uiso 1 1 calc R . .
C28 C 0.62727(16) 0.75183(18) 0.06389(14) 0.0497(6) Uani 1 1 d . . .
C16 C 0.58021(17) 1.00406(17) 0.40210(17) 0.0517(7) Uani 1 1 d . . .
C21 C 0.53563(18) 1.04985(18) 0.33222(18) 0.0573(7) Uani 1 1 d . . .
C13 C 0.84576(16) 0.87361(15) 0.37754(15) 0.0504(7) Uani 1 1 d . . .
H13A H 0.8427 0.9034 0.3271 0.061 Uiso 1 1 calc R . .
H13B H 0.9074 0.8842 0.4141 0.061 Uiso 1 1 calc R . .
C25 C 0.86603(16) 0.75267(17) 0.29215(15) 0.0556(7) Uani 1 1 d . . .
H25A H 0.8756 0.6909 0.2943 0.067 Uiso 1 1 calc R . .
H25B H 0.9260 0.7800 0.2940 0.067 Uiso 1 1 calc R . .
C14 C 0.76967(17) 0.90755(16) 0.41446(15) 0.0526(7) Uani 1 1 d . . .
H14A H 0.7771 0.8829 0.4678 0.063 Uiso 1 1 calc R . .
H14B H 0.7747 0.9696 0.4199 0.063 Uiso 1 1 calc R . .
C2 C 0.71497(19) 0.4765(2) 0.67053(16) 0.0612(8) Uani 1 1 d . . .
C17 C 0.60491(19) 1.0465(2) 0.47644(18) 0.0660(8) Uani 1 1 d . . .
C29 C 0.60629(18) 0.66756(18) 0.03599(16) 0.0553(7) Uani 1 1 d . . .
C10 C 0.68651(17) 0.67436(15) 0.48893(14) 0.0500(7) Uani 1 1 d . . .
H10A H 0.6192 0.6833 0.4672 0.060 Uiso 1 1 calc R . .
H10B H 0.7127 0.7273 0.5155 0.060 Uiso 1 1 calc R . .
C20 C 0.5158(2) 1.1366(2) 0.3382(2) 0.0758(9) Uani 1 1 d . . .
H20 H 0.4853 1.1665 0.2917 0.091 Uiso 1 1 calc R . .
C15 C 0.59656(17) 0.90843(16) 0.39539(16) 0.0582(7) Uani 1 1 d . . .
H15A H 0.6076 0.8833 0.4489 0.070 Uiso 1 1 calc R . .
H15B H 0.5392 0.8830 0.3619 0.070 Uiso 1 1 calc R . .
C3 C 0.66203(19) 0.46416(17) 0.59268(17) 0.0627(8) Uani 1 1 d . . .
H3A H 0.6308 0.4120 0.5793 0.075 Uiso 1 1 calc R . .
C23 C 0.6521(2) 1.0014(2) 0.55440(17) 0.0930(11) Uani 1 1 d . . .
H23A H 0.7142 0.9833 0.5529 0.139 Uiso 1 1 calc R . .
H23B H 0.6155 0.9521 0.5610 0.139 Uiso 1 1 calc R . .
H23C H 0.6569 1.0401 0.5990 0.139 Uiso 1 1 calc R . .
C26 C 0.79490(17) 0.77629(17) 0.21412(15) 0.0558(7) Uani 1 1 d . . .
H26A H 0.7909 0.8384 0.2085 0.067 Uiso 1 1 calc R . .
H26B H 0.8145 0.7531 0.1685 0.067 Uiso 1 1 calc R . .
C9 C 0.8082(2) 0.7016(2) 0.65660(17) 0.0976(12) Uani 1 1 d . . .
H9A H 0.8438 0.6973 0.7122 0.146 Uiso 1 1 calc R . .
H9B H 0.7641 0.7482 0.6508 0.146 Uiso 1 1 calc R . .
H9C H 0.8504 0.7120 0.6232 0.146 Uiso 1 1 calc R . .
C22 C 0.50774(19) 1.0089(2) 0.24954(17) 0.0804(9) Uani 1 1 d . . .
H22A H 0.4608 1.0438 0.2139 0.121 Uiso 1 1 calc R . .
H22B H 0.4825 0.9527 0.2535 0.121 Uiso 1 1 calc R . .
H22C H 0.5622 1.0043 0.2286 0.121 Uiso 1 1 calc R . .
C33 C 0.64987(19) 0.81345(18) 0.01235(16) 0.0601(7) Uani 1 1 d . . .
C7 C 0.76100(19) 0.5541(2) 0.68800(16) 0.0626(8) Uani 1 1 d . . .
H7 H 0.7976 0.5638 0.7404 0.075 Uiso 1 1 calc R . .
C12 C 0.87833(17) 0.73274(16) 0.43751(16) 0.0602(8) Uani 1 1 d . . .
H12A H 0.9443 0.7232 0.4398 0.072 Uiso 1 1 calc R . .
H12B H 0.8754 0.7672 0.4840 0.072 Uiso 1 1 calc R . .
C8 C 0.59255(19) 0.50754(17) 0.44830(15) 0.0711(9) Uani 1 1 d . . .
H8A H 0.5585 0.5584 0.4260 0.107 Uiso 1 1 calc R . .
H8B H 0.5486 0.4625 0.4507 0.107 Uiso 1 1 calc R . .
H8C H 0.6322 0.4897 0.4146 0.107 Uiso 1 1 calc R . .
C6 C 0.75523(19) 0.61837(18) 0.63092(16) 0.0567(7) Uani 1 1 d . . .
C35 C 0.5685(2) 0.60186(17) 0.08459(17) 0.0766(9) Uani 1 1 d . . .
H35A H 0.6184 0.5835 0.1299 0.115 Uiso 1 1 calc R . .
H35B H 0.5444 0.5532 0.0510 0.115 Uiso 1 1 calc R . .
H35C H 0.5187 0.6271 0.1038 0.115 Uiso 1 1 calc R . .
C18 C 0.5841(2) 1.1345(2) 0.4784(2) 0.0848(10) Uani 1 1 d . . .
H18 H 0.6011 1.1634 0.5276 0.102 Uiso 1 1 calc R . .
C19 C 0.5396(3) 1.1792(2) 0.4101(3) 0.0868(11) Uani 1 1 d . . .
C30 C 0.61566(19) 0.6453(2) -0.04001(18) 0.0684(8) Uani 1 1 d . . .
H30 H 0.6031 0.5890 -0.0579 0.082 Uiso 1 1 calc R . .
C31 C 0.6429(2) 0.7035(2) -0.08968(18) 0.0709(9) Uani 1 1 d . . .
C1 C 0.7215(2) 0.4078(2) 0.73461(18) 0.0940(11) Uani 1 1 d . . .
H1A H 0.6894 0.4271 0.7736 0.141 Uiso 1 1 calc R . .
H1B H 0.7866 0.3970 0.7612 0.141 Uiso 1 1 calc R . .
H1C H 0.6926 0.3558 0.7096 0.141 Uiso 1 1 calc R . .
C34 C 0.6610(2) 0.90807(19) 0.03355(19) 0.0971(11) Uani 1 1 d . . .
H34A H 0.6046 0.9289 0.0455 0.146 Uiso 1 1 calc R . .
H34B H 0.6720 0.9395 -0.0114 0.146 Uiso 1 1 calc R . .
H34C H 0.7136 0.9158 0.0800 0.146 Uiso 1 1 calc R . .
C24 C 0.5186(3) 1.2750(2) 0.4160(3) 0.1465(19) Uani 1 1 d . . .
H24A H 0.5378 1.2927 0.4716 0.220 Uiso 1 1 calc R . .
H24B H 0.4521 1.2848 0.3950 0.220 Uiso 1 1 calc R . .
H24C H 0.5527 1.3074 0.3851 0.220 Uiso 1 1 calc R . .
C32 C 0.6576(2) 0.7876(2) -0.06326(18) 0.0746(9) Uani 1 1 d . . .
H32 H 0.6733 0.8283 -0.0974 0.090 Uiso 1 1 calc R . .
C36 C 0.6539(2) 0.6770(2) -0.17241(18) 0.1110(13) Uani 1 1 d . . .
H36A H 0.6221 0.7178 -0.2124 0.166 Uiso 1 1 calc R . .
H36B H 0.6268 0.6210 -0.1860 0.166 Uiso 1 1 calc R . .
H36C H 0.7197 0.6754 -0.1710 0.166 Uiso 1 1 calc R . .
O1 O 0.5178(2) 0.4880(2) 0.2416(2) 0.2011(15) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 N3 2.0814(19) . ?
Co1 N1 2.0959(18) . ?
Co1 N2 2.1192(19) . ?
Co1 N4 2.2189(18) . ?
Co1 Cl1 2.3108(7) . ?
N4 C25 1.471(3) . ?
N4 C13 1.476(3) . ?
N4 C12 1.487(3) . ?
N3 C26 1.484(3) . ?
N3 C27 1.496(3) . ?
N2 C14 1.479(3) . ?
N2 C15 1.491(3) . ?
N1 C11 1.477(3) . ?
N1 C10 1.485(3) . ?
C5 C6 1.393(3) . ?
C5 C4 1.395(3) . ?
C5 C10 1.511(3) . ?
C4 C3 1.392(3) . ?
C4 C8 1.515(3) . ?
C27 C28 1.507(3) . ?
C11 C12 1.477(3) . ?
C28 C33 1.399(3) . ?
C28 C29 1.401(3) . ?
C16 C17 1.395(4) . ?
C16 C21 1.399(3) . ?
C16 C15 1.515(3) . ?
C21 C20 1.390(4) . ?
C21 C22 1.507(4) . ?
C13 C14 1.514(3) . ?
C25 C26 1.510(3) . ?
C2 C3 1.370(3) . ?
C2 C7 1.377(4) . ?
C2 C1 1.516(3) . ?
C17 C18 1.404(4) . ?
C17 C23 1.506(4) . ?
C29 C30 1.387(4) . ?
C29 C35 1.511(3) . ?
C20 C19 1.360(4) . ?
C9 C6 1.514(3) . ?
C33 C32 1.388(4) . ?
C33 C34 1.514(4) . ?
C7 C6 1.384(3) . ?
C18 C19 1.370(4) . ?
C19 C24 1.529(4) . ?
C30 C31 1.371(4) . ?
C31 C32 1.381(4) . ?
C31 C36 1.523(4) . ?

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
N3 Co1 N1 121.76(8) . . ?
N3 Co1 N2 109.82(8) . . ?
N1 Co1 N2 120.34(8) . . ?
N3 Co1 N4 81.63(7) . . ?
N1 Co1 N4 79.65(7) . . ?
N2 Co1 N4 80.29(7) . . ?
N3 Co1 Cl1 100.75(5) . . ?
N1 Co1 Cl1 95.65(6) . . ?
N2 Co1 Cl1 102.55(6) . . ?
N4 Co1 Cl1 175.29(5) . . ?
C25 N4 C13 112.25(19) . . ?
C25 N4 C12 112.99(19) . . ?
C13 N4 C12 109.09(19) . . ?
C25 N4 Co1 105.66(14) . . ?
C13 N4 Co1 108.28(14) . . ?
C12 N4 Co1 108.35(14) . . ?
C26 N3 C27 113.17(19) . . ?
C26 N3 Co1 110.48(14) . . ?
C27 N3 Co1 114.26(14) . . ?
C14 N2 C15 112.91(19) . . ?
C14 N2 Co1 108.68(14) . . ?
C15 N2 Co1 114.52(14) . . ?
C11 N1 C10 115.53(19) . . ?
C11 N1 Co1 113.20(14) . . ?
C10 N1 Co1 110.02(14) . . ?
C6 C5 C4 119.5(2) . . ?
C6 C5 C10 121.2(2) . . ?
C4 C5 C10 119.2(2) . . ?
C3 C4 C5 118.9(2) . . ?
C3 C4 C8 119.1(2) . . ?
C5 C4 C8 122.0(2) . . ?
N3 C27 C28 115.3(2) . . ?
N1 C11 C12 110.4(2) . . ?
C33 C28 C29 119.5(2) . . ?
C33 C28 C27 121.2(2) . . ?
C29 C28 C27 119.2(2) . . ?
C17 C16 C21 119.4(3) . . ?
C17 C16 C15 121.7(3) . . ?
C21 C16 C15 118.9(2) . . ?
C20 C21 C16 119.4(3) . . ?
C20 C21 C22 117.9(3) . . ?
C16 C21 C22 122.7(3) . . ?
N4 C13 C14 109.99(19) . . ?
N4 C25 C26 110.44(19) . . ?
N2 C14 C13 108.6(2) . . ?
C3 C2 C7 117.1(3) . . ?
C3 C2 C1 121.2(3) . . ?
C7 C2 C1 121.7(3) . . ?
C16 C17 C18 118.4(3) . . ?
C16 C17 C23 122.5(3) . . ?
C18 C17 C23 119.0(3) . . ?
C30 C29 C28 119.1(3) . . ?
C30 C29 C35 119.2(3) . . ?
C28 C29 C35 121.6(3) . . ?
N1 C10 C5 117.02(19) . . ?
C19 C20 C21 122.0(3) . . ?
N2 C15 C16 115.91(19) . . ?
C2 C3 C4 122.7(3) . . ?
N3 C26 C25 109.2(2) . . ?
C32 C33 C28 118.6(3) . . ?
C32 C33 C34 118.4(3) . . ?
C28 C33 C34 122.9(3) . . ?
C2 C7 C6 122.9(3) . . ?
C11 C12 N4 111.8(2) . . ?
C7 C6 C5 118.9(2) . . ?
C7 C6 C9 118.6(3) . . ?
C5 C6 C9 122.4(3) . . ?
C19 C18 C17 122.2(3) . . ?
C20 C19 C18 118.5(3) . . ?
C20 C19 C24 121.7(4) . . ?
C18 C19 C24 119.9(4) . . ?
C31 C30 C29 122.2(3) . . ?
C30 C31 C32 117.9(3) . . ?
C30 C31 C36 121.0(3) . . ?
C32 C31 C36 121.0(3) . . ?
C31 C32 C33 122.4(3) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.041
####################################################################### 
# 
# 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_complex4b
_database_code_depnum_ccdc_archive 'CCDC 1456819'
_audit_update_record             
;
2016-03-01 deposited with the CCDC.
2016-05-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H36 Cl Co N4 O7'
_chemical_formula_weight         574.94

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   p-1

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

_cell_length_a                   9.0274(8)
_cell_length_b                   12.0143(10)
_cell_length_c                   14.0393(10)
_cell_angle_alpha                70.559(7)
_cell_angle_beta                 76.564(7)
_cell_angle_gamma                87.579(7)
_cell_volume                     1395.6(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9651
_cell_measurement_theta_min      3
_cell_measurement_theta_max      25.3

_exptl_crystal_description       plate
_exptl_crystal_colour            brown
_exptl_crystal_size_max          .9
_exptl_crystal_size_mid          .09
_exptl_crystal_size_min          .05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             604
_exptl_absorpt_coefficient_mu    0.757
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.63602
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'face installed'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9651
_diffrn_reflns_av_R_equivalents  0.0478
_diffrn_reflns_av_sigmaI/netI    0.0696
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.99
_diffrn_reflns_theta_max         25.25
_reflns_number_total             5040
_reflns_number_gt                3833
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_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)+(0.0828P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5040
_refine_ls_number_parameters     333
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0796
_refine_ls_R_factor_gt           0.0615
_refine_ls_wR_factor_ref         0.1861
_refine_ls_wR_factor_gt          0.1676
_refine_ls_goodness_of_fit_ref   1.188
_refine_ls_restrained_S_all      1.188
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.21281(6) 0.17000(4) 0.80736(4) 0.0452(2) Uani 1 1 d . . .
Cl1 Cl 0.68166(14) 0.36500(14) 0.71942(11) 0.0790(4) Uani 1 1 d . . .
N2 N 0.2064(3) 0.3456(2) 0.7828(2) 0.0363(7) Uani 1 1 d . . .
H2N H 0.2992 0.3686 0.7864 0.044 Uiso 1 1 calc R . .
N1 N 0.2746(3) 0.2185(2) 0.6499(2) 0.0391(7) Uani 1 1 d . . .
H1N H 0.1898 0.2050 0.6302 0.047 Uiso 1 1 calc R . .
N3 N 0.3484(5) 0.1145(3) 0.8692(3) 0.0694(11) Uani 1 1 d . . .
O3 O 0.5421(6) 0.3859(8) 0.7587(5) 0.210(4) Uani 1 1 d . . .
N4 N 0.0432(5) 0.1003(3) 0.8498(3) 0.0599(10) Uani 1 1 d . . .
O1 O 0.4269(6) 0.0683(4) 0.9233(4) 0.1326(18) Uani 1 1 d . . .
O7 O 0.0225(4) 0.7909(3) 0.3976(2) 0.0713(9) Uani 1 1 d . . .
H7 H 0.0843 0.7640 0.3589 0.107 Uiso 1 1 calc R . .
C14 C 0.1326(4) 0.4925(3) 0.8774(2) 0.0368(8) Uani 1 1 d . . .
C12 C 0.1925(5) 0.4053(3) 0.6741(3) 0.0439(9) Uani 1 1 d . . .
H12A H 0.2173 0.4891 0.6526 0.053 Uiso 1 1 calc R . .
H12B H 0.0893 0.3953 0.6683 0.053 Uiso 1 1 calc R . .
C5 C 0.3733(4) 0.1345(3) 0.5061(3) 0.0404(8) Uani 1 1 d . . .
C19 C 0.2380(4) 0.4865(3) 0.9381(3) 0.0424(9) Uani 1 1 d . . .
C4 C 0.2727(4) 0.0450(3) 0.5152(3) 0.0414(9) Uani 1 1 d . . .
O2 O -0.0644(5) 0.0398(4) 0.8900(3) 0.1039(15) Uani 1 1 d . . .
C15 C 0.0642(5) 0.5995(3) 0.8370(3) 0.0470(10) Uani 1 1 d . . .
O5 O 0.7607(10) 0.4478(7) 0.6390(6) 0.249(5) Uani 1 1 d . . .
C6 C 0.4498(4) 0.2067(3) 0.4076(3) 0.0470(10) Uani 1 1 d . . .
C2 C 0.3231(5) 0.1000(4) 0.3276(3) 0.0517(10) Uani 1 1 d . . .
C3 C 0.2482(5) 0.0293(4) 0.4256(3) 0.0500(10) Uani 1 1 d . . .
H3 H 0.1800 -0.0301 0.4322 0.060 Uiso 1 1 calc R . .
C18 C 0.2749(5) 0.5877(4) 0.9548(3) 0.0565(12) Uani 1 1 d . . .
H18 H 0.3446 0.5835 0.9953 0.068 Uiso 1 1 calc R . .
C10 C 0.3970(5) 0.1492(4) 0.6047(3) 0.0484(9) Uani 1 1 d . . .
H10A H 0.3991 0.0717 0.6557 0.058 Uiso 1 1 calc R . .
H10B H 0.4952 0.1891 0.5898 0.058 Uiso 1 1 calc R . .
C7 C 0.4226(5) 0.1878(4) 0.3200(3) 0.0564(11) Uani 1 1 d . . .
H7A H 0.4734 0.2362 0.2545 0.068 Uiso 1 1 calc R . .
C16 C 0.1078(5) 0.6981(4) 0.8563(3) 0.0587(12) Uani 1 1 d . . .
H16 H 0.0641 0.7696 0.8287 0.070 Uiso 1 1 calc R . .
C17 C 0.2126(6) 0.6948(4) 0.9140(4) 0.0640(14) Uani 1 1 d . . .
C13 C 0.0892(4) 0.3812(3) 0.8625(3) 0.0414(9) Uani 1 1 d . . .
H13A H -0.0069 0.3919 0.8413 0.050 Uiso 1 1 calc R . .
H13B H 0.0736 0.3174 0.9284 0.050 Uiso 1 1 calc R . .
C22 C 0.2569(7) 0.8049(5) 0.9326(5) 0.099(2) Uani 1 1 d . . .
H22A H 0.3238 0.7846 0.9794 0.149 Uiso 1 1 calc R . .
H22B H 0.1669 0.8384 0.9623 0.149 Uiso 1 1 calc R . .
H22C H 0.3079 0.8615 0.8678 0.149 Uiso 1 1 calc R . .
C11 C 0.3036(4) 0.3485(3) 0.6067(3) 0.0439(9) Uani 1 1 d . . .
H11A H 0.2902 0.3781 0.5361 0.053 Uiso 1 1 calc R . .
H11B H 0.4074 0.3676 0.6055 0.053 Uiso 1 1 calc R . .
O4 O 0.7798(9) 0.3255(8) 0.7800(7) 0.232(4) Uani 1 1 d . . .
C1 C 0.2951(6) 0.0786(5) 0.2322(3) 0.0747(14) Uani 1 1 d . . .
H1A H 0.1900 0.0911 0.2298 0.112 Uiso 1 1 calc R . .
H1B H 0.3187 -0.0011 0.2357 0.112 Uiso 1 1 calc R . .
H1C H 0.3588 0.1324 0.1708 0.112 Uiso 1 1 calc R . .
C20 C -0.0545(6) 0.6096(5) 0.7753(3) 0.0744(14) Uani 1 1 d . . .
H20A H -0.0823 0.6904 0.7508 0.112 Uiso 1 1 calc R . .
H20B H -0.1430 0.5614 0.8187 0.112 Uiso 1 1 calc R . .
H20C H -0.0142 0.5833 0.7172 0.112 Uiso 1 1 calc R . .
C9 C 0.5640(5) 0.3045(4) 0.3900(4) 0.0716(15) Uani 1 1 d . . .
H9A H 0.5114 0.3688 0.4073 0.107 Uiso 1 1 calc R . .
H9B H 0.6180 0.3317 0.3184 0.107 Uiso 1 1 calc R . .
H9C H 0.6350 0.2750 0.4331 0.107 Uiso 1 1 calc R . .
C21 C 0.3084(5) 0.3729(4) 0.9873(3) 0.0621(12) Uani 1 1 d . . .
H21A H 0.2306 0.3112 1.0202 0.093 Uiso 1 1 calc R . .
H21B H 0.3574 0.3820 1.0383 0.093 Uiso 1 1 calc R . .
H21C H 0.3825 0.3527 0.9350 0.093 Uiso 1 1 calc R . .
C8 C 0.1871(5) -0.0377(4) 0.6191(3) 0.0608(12) Uani 1 1 d . . .
H8A H 0.2584 -0.0780 0.6588 0.091 Uiso 1 1 calc R . .
H8B H 0.1268 -0.0944 0.6083 0.091 Uiso 1 1 calc R . .
H8C H 0.1216 0.0069 0.6561 0.091 Uiso 1 1 calc R . .
C23 C 0.0133(6) 0.7188(5) 0.5033(4) 0.0799(15) Uani 1 1 d . . .
H23A H 0.1023 0.7338 0.5242 0.120 Uiso 1 1 calc R . .
H23B H 0.0073 0.6370 0.5094 0.120 Uiso 1 1 calc R . .
H23C H -0.0760 0.7372 0.5471 0.120 Uiso 1 1 calc R . .
O6 O 0.6639(7) 0.2700(8) 0.6837(7) 0.227(4) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 N3 1.654(4) . ?
Co1 N4 1.659(4) . ?
Co1 N2 2.022(3) . ?
Co1 N1 2.034(3) . ?
Cl1 O3 1.302(5) . ?
Cl1 O5 1.308(6) . ?
Cl1 O4 1.334(6) . ?
Cl1 O6 1.419(6) . ?
N2 C12 1.487(4) . ?
N2 C13 1.511(4) . ?
N1 C11 1.484(5) . ?
N1 C10 1.506(5) . ?
N3 O1 1.151(5) . ?
N4 O2 1.150(4) . ?
O7 C23 1.433(5) . ?
C14 C15 1.402(5) . ?
C14 C19 1.402(5) . ?
C14 C13 1.502(5) . ?
C12 C11 1.516(5) . ?
C5 C4 1.391(5) . ?
C5 C6 1.396(5) . ?
C5 C10 1.515(5) . ?
C19 C18 1.381(5) . ?
C19 C21 1.500(6) . ?
C4 C3 1.399(5) . ?
C4 C8 1.512(5) . ?
C15 C16 1.391(5) . ?
C15 C20 1.505(6) . ?
C6 C7 1.398(5) . ?
C6 C9 1.515(5) . ?
C2 C7 1.376(5) . ?
C2 C3 1.382(5) . ?
C2 C1 1.522(5) . ?
C18 C17 1.377(7) . ?
C16 C17 1.373(7) . ?
C17 C22 1.517(6) . ?

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
N3 Co1 N4 118.6(2) . . ?
N3 Co1 N2 109.03(15) . . ?
N4 Co1 N2 114.45(16) . . ?
N3 Co1 N1 115.87(16) . . ?
N4 Co1 N1 109.43(14) . . ?
N2 Co1 N1 84.76(11) . . ?
O3 Cl1 O5 118.3(6) . . ?
O3 Cl1 O4 120.6(5) . . ?
O5 Cl1 O4 103.5(6) . . ?
O3 Cl1 O6 103.3(4) . . ?
O5 Cl1 O6 105.7(5) . . ?
O4 Cl1 O6 103.6(5) . . ?
C12 N2 C13 113.9(3) . . ?
C12 N2 Co1 107.64(19) . . ?
C13 N2 Co1 114.9(2) . . ?
C11 N1 C10 114.3(3) . . ?
C11 N1 Co1 108.6(2) . . ?
C10 N1 Co1 116.8(2) . . ?
O1 N3 Co1 170.8(5) . . ?
O2 N4 Co1 169.7(4) . . ?
C15 C14 C19 119.9(3) . . ?
C15 C14 C13 121.5(3) . . ?
C19 C14 C13 118.5(3) . . ?
N2 C12 C11 106.9(3) . . ?
C4 C5 C6 119.5(3) . . ?
C4 C5 C10 118.2(3) . . ?
C6 C5 C10 122.3(3) . . ?
C18 C19 C14 118.9(4) . . ?
C18 C19 C21 119.2(4) . . ?
C14 C19 C21 121.9(3) . . ?
C5 C4 C3 119.6(3) . . ?
C5 C4 C8 122.7(3) . . ?
C3 C4 C8 117.8(3) . . ?
C16 C15 C14 118.1(4) . . ?
C16 C15 C20 119.8(4) . . ?
C14 C15 C20 122.0(3) . . ?
C5 C6 C7 119.1(3) . . ?
C5 C6 C9 123.3(3) . . ?
C7 C6 C9 117.6(3) . . ?
C7 C2 C3 118.0(3) . . ?
C7 C2 C1 122.1(4) . . ?
C3 C2 C1 119.9(4) . . ?
C2 C3 C4 121.6(3) . . ?
C17 C18 C19 122.6(4) . . ?
N1 C10 C5 112.8(3) . . ?
C2 C7 C6 122.1(4) . . ?
C17 C16 C15 123.0(4) . . ?
C16 C17 C18 117.5(4) . . ?
C16 C17 C22 121.1(5) . . ?
C18 C17 C22 121.4(5) . . ?
C14 C13 N2 113.8(3) . . ?
N1 C11 C12 108.8(3) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.584
_refine_diff_density_min         -0.501
_refine_diff_density_rms         0.068
####################################################################### 
# 
# 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_complex5
_database_code_depnum_ccdc_archive 'CCDC 1456820'
_audit_update_record             
;
2016-03-01 deposited with the CCDC.
2016-05-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H41 Cl2 Co N4 O2'
_chemical_formula_weight         559.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n

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

_cell_length_a                   11.0311(13)
_cell_length_b                   12.658(2)
_cell_length_c                   20.544(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.626(13)
_cell_angle_gamma                90.00
_cell_volume                     2849.3(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    11423
_cell_measurement_theta_min      3
_cell_measurement_theta_max      25.3

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          .34
_exptl_crystal_size_mid          .31
_exptl_crystal_size_min          .25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1184
_exptl_absorpt_coefficient_mu    0.817
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.60928
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'face installed'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11423
_diffrn_reflns_av_R_equivalents  0.1072
_diffrn_reflns_av_sigmaI/netI    0.2261
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.03
_diffrn_reflns_theta_max         25.25
_reflns_number_total             5147
_reflns_number_gt                1928
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_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)+(0.0000P)²+4.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5147
_refine_ls_number_parameters     315
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.2328
_refine_ls_R_factor_gt           0.0918
_refine_ls_wR_factor_ref         0.1759
_refine_ls_wR_factor_gt          0.1296
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.092
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.36773(10) 0.83610(11) 0.75054(6) 0.0514(4) Uani 1 1 d . . .
Cl1 Cl 0.4786(2) 0.9850(2) 0.75810(13) 0.0878(10) Uani 1 1 d . . .
Cl2 Cl 0.6573(3) 0.5106(2) 0.21752(19) 0.1271(14) Uani 1 1 d . . .
N3 N 0.3373(6) 0.8465(6) 0.8455(3) 0.059(2) Uani 1 1 d . . .
H3 H 0.2942 0.9073 0.8485 0.071 Uiso 1 1 calc R . .
N2 N 0.2436(6) 0.7272(6) 0.7430(3) 0.056(2) Uani 1 1 d . . .
H2 H 0.2826 0.6640 0.7492 0.067 Uiso 1 1 calc R . .
N1 N 0.3436(6) 0.8345(6) 0.6530(3) 0.060(2) Uani 1 1 d . . .
H1 H 0.2922 0.8896 0.6422 0.072 Uiso 1 1 calc R . .
C4 C 0.3530(8) 0.9497(9) 0.5145(4) 0.060(3) Uani 1 1 d . . .
C11 C 0.2718(8) 0.7398(7) 0.6300(4) 0.066(3) Uani 1 1 d . . .
H11A H 0.3242 0.6781 0.6308 0.080 Uiso 1 1 calc R . .
H11B H 0.2332 0.7501 0.5856 0.080 Uiso 1 1 calc R . .
C15 C 0.4483(7) 0.8572(8) 0.8960(4) 0.067(3) Uani 1 1 d . . .
H15A H 0.4802 0.9284 0.8945 0.080 Uiso 1 1 calc R . .
H15B H 0.5112 0.8089 0.8851 0.080 Uiso 1 1 calc R . .
C12 C 0.1766(7) 0.7256(8) 0.6767(4) 0.058(3) Uani 1 1 d . . .
H12A H 0.1173 0.7824 0.6715 0.069 Uiso 1 1 calc R . .
H12B H 0.1342 0.6589 0.6686 0.069 Uiso 1 1 calc R . .
C14 C 0.2514(8) 0.7594(8) 0.8581(4) 0.063(3) Uani 1 1 d . . .
H14A H 0.2053 0.7788 0.8937 0.075 Uiso 1 1 calc R . .
H14B H 0.2970 0.6955 0.8705 0.075 Uiso 1 1 calc R . .
C19 C 0.3677(10) 0.7903(12) 1.0922(5) 0.081(4) Uani 1 1 d . . .
C5 C 0.4110(8) 0.8606(9) 0.5396(5) 0.059(3) Uani 1 1 d . . .
C18 C 0.3324(8) 0.8837(10) 1.0631(5) 0.082(4) Uani 1 1 d . . .
H18 H 0.2914 0.9326 1.0863 0.098 Uiso 1 1 calc R . .
C13 C 0.1655(7) 0.7401(7) 0.7964(4) 0.055(3) Uani 1 1 d . . .
H13A H 0.1175 0.6769 0.8009 0.066 Uiso 1 1 calc R . .
H13B H 0.1105 0.7995 0.7875 0.066 Uiso 1 1 calc R . .
C8 C 0.5065(10) 0.6783(9) 0.5221(5) 0.110(4) Uani 1 1 d . . .
H8A H 0.5047 0.6278 0.4870 0.165 Uiso 1 1 calc R . .
H8B H 0.4692 0.6481 0.5577 0.165 Uiso 1 1 calc R . .
H8C H 0.5897 0.6965 0.5368 0.165 Uiso 1 1 calc R . .
C21 C 0.4570(8) 0.7397(9) 0.9955(5) 0.064(3) Uani 1 1 d . . .
C17 C 0.3562(8) 0.9088(9) 0.9983(5) 0.066(3) Uani 1 1 d . . .
C20 C 0.4296(9) 0.7184(10) 1.0582(5) 0.078(3) Uani 1 1 d . . .
H20 H 0.4534 0.6543 1.0778 0.094 Uiso 1 1 calc R . .
N4 N 0.4941(9) 0.7514(8) 0.7694(4) 0.089(3) Uani 1 1 d D . .
C2 C 0.3372(10) 0.8719(11) 0.4063(5) 0.079(4) Uani 1 1 d . . .
C16 C 0.4194(8) 0.8337(9) 0.9657(4) 0.058(3) Uani 1 1 d . . .
C10 C 0.4505(7) 0.8534(8) 0.6133(4) 0.063(3) Uani 1 1 d . . .
H10A H 0.5087 0.7962 0.6216 0.075 Uiso 1 1 calc R . .
H10B H 0.4913 0.9185 0.6280 0.075 Uiso 1 1 calc R . .
C3 C 0.3170(8) 0.9563(9) 0.4466(5) 0.073(3) Uani 1 1 d . . .
H3A H 0.2797 1.0173 0.4288 0.088 Uiso 1 1 calc R . .
C7 C 0.3979(10) 0.7853(11) 0.4322(6) 0.088(4) Uani 1 1 d . . .
H7 H 0.4131 0.7302 0.4043 0.105 Uiso 1 1 calc R . .
C6 C 0.4377(9) 0.7761(10) 0.4979(6) 0.076(3) Uani 1 1 d . . .
C24 C 0.3386(9) 0.7662(10) 1.1617(5) 0.113(5) Uani 1 1 d . . .
H24A H 0.3988 0.7987 1.1929 0.170 Uiso 1 1 calc R . .
H24B H 0.3393 0.6912 1.1685 0.170 Uiso 1 1 calc R . .
H24C H 0.2593 0.7937 1.1674 0.170 Uiso 1 1 calc R . .
C9 C 0.3275(9) 1.0453(8) 0.5553(5) 0.083(3) Uani 1 1 d . . .
H9A H 0.2510 1.0359 0.5726 0.125 Uiso 1 1 calc R . .
H9B H 0.3238 1.1074 0.5284 0.125 Uiso 1 1 calc R . .
H9C H 0.3916 1.0529 0.5908 0.125 Uiso 1 1 calc R . .
C22 C 0.5324(8) 0.6567(8) 0.9645(5) 0.090(4) Uani 1 1 d . . .
H22A H 0.4873 0.6310 0.9249 0.136 Uiso 1 1 calc R . .
H22B H 0.5498 0.5991 0.9946 0.136 Uiso 1 1 calc R . .
H22C H 0.6075 0.6877 0.9546 0.136 Uiso 1 1 calc R . .
C1 C 0.2925(10) 0.8809(13) 0.3318(5) 0.173(8) Uani 1 1 d . . .
H1A H 0.2882 0.8117 0.3125 0.260 Uiso 1 1 calc R . .
H1B H 0.3487 0.9236 0.3109 0.260 Uiso 1 1 calc R . .
H1C H 0.2132 0.9129 0.3260 0.260 Uiso 1 1 calc R . .
C23 C 0.3136(9) 1.0126(8) 0.9685(5) 0.089(4) Uani 1 1 d . . .
H23A H 0.2439 1.0012 0.9367 0.134 Uiso 1 1 calc R . .
H23B H 0.3780 1.0441 0.9475 0.134 Uiso 1 1 calc R . .
H23C H 0.2915 1.0589 1.0022 0.134 Uiso 1 1 calc R . .
O1 O 0.5414(9) 0.7093(9) 0.7327(5) 0.153(4) Uani 1 1 d D . .
O2 O 0.8957(16) 0.968(2) 0.8229(11) 0.392(14) Uani 1 1 d D . .
H2A H 0.8819 0.9348 0.7886 0.588 Uiso 1 1 calc R . .
C1A C 1.0239(16) 0.9748(14) 0.8408(8) 0.200(11) Uani 1 1 d D . .
H1AA H 1.0618 1.0034 0.8049 0.300 Uiso 1 1 calc R . .
H1AB H 1.0560 0.9055 0.8512 0.300 Uiso 1 1 calc R . .
H1AC H 1.0403 1.0199 0.8784 0.300 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 N4 1.765(10) . ?
Co1 N2 1.936(7) . ?
Co1 N1 1.990(6) . ?
Co1 N3 2.022(6) . ?
Co1 Cl1 2.243(3) . ?
N3 C14 1.495(10) . ?
N3 C15 1.518(9) . ?
N2 C12 1.472(9) . ?
N2 C13 1.481(9) . ?
N1 C11 1.484(10) . ?
N1 C10 1.528(9) . ?
C4 C5 1.368(12) . ?
C4 C3 1.407(12) . ?
C4 C9 1.517(12) . ?
C11 C12 1.513(10) . ?
C15 C16 1.530(11) . ?
C14 C13 1.512(10) . ?
C19 C18 1.361(14) . ?
C19 C20 1.375(14) . ?
C19 C24 1.531(12) . ?
C5 C6 1.423(13) . ?
C5 C10 1.529(11) . ?
C18 C17 1.423(13) . ?
C8 C6 1.506(13) . ?
C21 C16 1.381(12) . ?
C21 C20 1.382(12) . ?
C21 C22 1.525(12) . ?
C17 C16 1.395(12) . ?
C17 C23 1.503(12) . ?
N4 O1 1.103(9) . ?
C2 C7 1.360(14) . ?
C2 C3 1.384(14) . ?
C2 C1 1.558(13) . ?
C7 C6 1.376(13) . ?
O2 C1A 1.421(13) . ?

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
N4 Co1 N2 96.8(4) . . ?
N4 Co1 N1 103.0(4) . . ?
N2 Co1 N1 84.3(3) . . ?
N4 Co1 N3 92.5(4) . . ?
N2 Co1 N3 85.9(3) . . ?
N1 Co1 N3 162.6(3) . . ?
N4 Co1 Cl1 94.9(4) . . ?
N2 Co1 Cl1 168.2(2) . . ?
N1 Co1 Cl1 95.0(2) . . ?
N3 Co1 Cl1 91.6(2) . . ?
C14 N3 C15 115.1(7) . . ?
C14 N3 Co1 107.3(5) . . ?
C15 N3 Co1 117.0(5) . . ?
C12 N2 C13 114.4(6) . . ?
C12 N2 Co1 111.1(6) . . ?
C13 N2 Co1 109.2(5) . . ?
C11 N1 C10 111.9(7) . . ?
C11 N1 Co1 109.5(5) . . ?
C10 N1 Co1 120.9(5) . . ?
C5 C4 C3 119.3(10) . . ?
C5 C4 C9 123.8(9) . . ?
C3 C4 C9 116.9(10) . . ?
N1 C11 C12 106.1(7) . . ?
N3 C15 C16 112.5(7) . . ?
N2 C12 C11 105.8(7) . . ?
N3 C14 C13 108.8(7) . . ?
C18 C19 C20 119.1(11) . . ?
C18 C19 C24 120.1(12) . . ?
C20 C19 C24 120.8(12) . . ?
C4 C5 C6 120.9(10) . . ?
C4 C5 C10 119.4(9) . . ?
C6 C5 C10 119.7(10) . . ?
C19 C18 C17 122.0(11) . . ?
N2 C13 C14 106.1(6) . . ?
C16 C21 C20 119.7(10) . . ?
C16 C21 C22 124.0(9) . . ?
C20 C21 C22 116.3(10) . . ?
C16 C17 C18 117.0(10) . . ?
C16 C17 C23 123.4(10) . . ?
C18 C17 C23 119.6(10) . . ?
C19 C20 C21 121.2(11) . . ?
O1 N4 Co1 124.6(10) . . ?
C7 C2 C3 119.6(11) . . ?
C7 C2 C1 121.9(13) . . ?
C3 C2 C1 118.5(13) . . ?
C21 C16 C17 121.0(10) . . ?
C21 C16 C15 119.9(9) . . ?
C17 C16 C15 119.1(10) . . ?
N1 C10 C5 112.9(7) . . ?
C2 C3 C4 120.0(11) . . ?
C2 C7 C6 122.6(12) . . ?
C7 C6 C5 117.5(12) . . ?
C7 C6 C8 119.0(12) . . ?
C5 C6 C8 123.5(10) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.614
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.080
####################################################################### 
# 
# 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_added_by_encifer
_database_code_depnum_ccdc_archive 'CCDC 1456821'
_audit_update_record             
;
2016-03-01 deposited with the CCDC.
2016-05-31 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H30 N4 O2'
_chemical_formula_weight         382.50

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/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                   4.9480(4)
_cell_length_b                   17.236(2)
_cell_length_c                   12.6051(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.761(7)
_cell_angle_gamma                90.00
_cell_volume                     1074.47(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4085
_cell_measurement_theta_min      3.2
_cell_measurement_theta_max      25.3

_exptl_crystal_description       niddle
_exptl_crystal_colour            white
_exptl_crystal_size_max          1
_exptl_crystal_size_mid          .08
_exptl_crystal_size_min          .06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.182
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             412
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.34099
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'face installed'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4085
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_av_sigmaI/netI    0.0673
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.23
_diffrn_reflns_theta_max         25.25
_reflns_number_total             1936
_reflns_number_gt                1091
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_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)+(0.0675P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1936
_refine_ls_number_parameters     130
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1370
_refine_ls_R_factor_gt           0.0774
_refine_ls_wR_factor_ref         0.2035
_refine_ls_wR_factor_gt          0.1764
_refine_ls_goodness_of_fit_ref   1.230
_refine_ls_restrained_S_all      1.230
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2157(6) 0.61918(19) 1.0972(2) 0.1020(12) Uani 1 1 d . . .
N1 N 0.2963(5) 0.58135(18) 0.94017(18) 0.0551(8) Uani 1 1 d . . .
N2 N 0.1397(7) 0.6224(2) 1.0042(2) 0.0746(11) Uani 1 1 d . . .
C5 C 0.4129(6) 0.6013(2) 0.7509(2) 0.0471(9) Uani 1 1 d . . .
C4 C 0.5199(7) 0.5449(2) 0.6834(2) 0.0499(9) Uani 1 1 d . . .
C2 C 0.7927(7) 0.6435(2) 0.6003(2) 0.0562(10) Uani 1 1 d . . .
C6 C 0.4954(7) 0.6779(2) 0.7428(2) 0.0522(9) Uani 1 1 d . . .
C11 C 0.5362(7) 0.5396(2) 0.9772(2) 0.0583(10) Uani 1 1 d . . .
H11A H 0.6311 0.5699 1.0314 0.070 Uiso 1 1 calc R . .
H11B H 0.6564 0.5325 0.9186 0.070 Uiso 1 1 calc R . .
C7 C 0.6847(7) 0.6977(2) 0.6668(2) 0.0585(10) Uani 1 1 d . . .
H7 H 0.7387 0.7492 0.6612 0.070 Uiso 1 1 calc R . .
C3 C 0.7079(7) 0.5677(2) 0.6098(2) 0.0571(10) Uani 1 1 d . . .
H3 H 0.7792 0.5303 0.5653 0.069 Uiso 1 1 calc R . .
C10 C 0.2002(7) 0.5793(2) 0.8294(2) 0.0534(9) Uani 1 1 d . . .
H10A H 0.0480 0.6144 0.8206 0.064 Uiso 1 1 calc R . .
H10B H 0.1358 0.5274 0.8130 0.064 Uiso 1 1 calc R . .
C8 C 0.4383(8) 0.4609(2) 0.6872(3) 0.0758(13) Uani 1 1 d . . .
H8A H 0.5253 0.4329 0.6320 0.114 Uiso 1 1 calc R . .
H8B H 0.2457 0.4568 0.6772 0.114 Uiso 1 1 calc R . .
H8C H 0.4918 0.4394 0.7549 0.114 Uiso 1 1 calc R . .
C1 C 0.9964(8) 0.6662(3) 0.5189(2) 0.0791(13) Uani 1 1 d . . .
H1A H 1.1677 0.6427 0.5369 0.119 Uiso 1 1 calc R . .
H1B H 1.0159 0.7216 0.5181 0.119 Uiso 1 1 calc R . .
H1C H 0.9351 0.6486 0.4500 0.119 Uiso 1 1 calc R . .
C9 C 0.3838(9) 0.7410(2) 0.8118(3) 0.0786(13) Uani 1 1 d . . .
H9A H 0.1898 0.7403 0.8065 0.118 Uiso 1 1 calc R . .
H9B H 0.4486 0.7905 0.7886 0.118 Uiso 1 1 calc R . .
H9C H 0.4419 0.7325 0.8843 0.118 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N2 1.222(3) . ?
N1 N2 1.338(4) . ?
N1 C11 1.453(4) . ?
N1 C10 1.462(4) . ?
C5 C6 1.387(5) . ?
C5 C4 1.406(4) . ?
C5 C10 1.515(4) . ?
C4 C3 1.391(4) . ?
C4 C8 1.503(5) . ?
C2 C7 1.374(5) . ?
C2 C3 1.380(5) . ?
C2 C1 1.511(4) . ?
C6 C7 1.403(4) . ?
C6 C9 1.509(4) . ?
C11 C11 1.527(6) 3_667 ?

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 N1 C11 123.4(3) . . ?
N2 N1 C10 114.3(3) . . ?
C11 N1 C10 122.2(3) . . ?
O1 N2 N1 112.8(3) . . ?
C6 C5 C4 119.8(3) . . ?
C6 C5 C10 119.9(3) . . ?
C4 C5 C10 120.3(3) . . ?
C3 C4 C5 118.7(3) . . ?
C3 C4 C8 118.6(3) . . ?
C5 C4 C8 122.6(3) . . ?
C7 C2 C3 117.8(3) . . ?
C7 C2 C1 121.3(4) . . ?
C3 C2 C1 121.0(3) . . ?
C5 C6 C7 119.1(3) . . ?
C5 C6 C9 122.1(3) . . ?
C7 C6 C9 118.8(3) . . ?
N1 C11 C11 111.4(3) . 3_667 ?
C2 C7 C6 122.1(4) . . ?
C2 C3 C4 122.5(3) . . ?
N1 C10 C5 113.9(3) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.042
