# Electronic Supplementary Material (ESI) for MedChemComm.
# 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_czh-zhr-c-co01-1001
_database_code_depnum_ccdc_archive 'CCDC 1438494'
_audit_update_record             
;
2015-11-24 deposited with the CCDC.
2016-04-01 downloaded from the CCDC.
;
_audit_creation_date             2014-10-17
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '2(C14 H10 Br Co0.5 N2 O), 2(O1)'
_chemical_formula_sum            'C28 H20 Br2 Co N4 O4'
_chemical_formula_weight         695.23
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           52
_space_group_name_H-M_alt        'P n n a'
_space_group_name_Hall           '-P 2a 2bc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z'
3 'x, -y+1/2, -z+1/2'
4 '-x+1/2, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x-1/2, y, -z'
7 '-x, y-1/2, z-1/2'
8 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   14.6162(11)
_cell_length_b                   16.3774(8)
_cell_length_c                   12.5927(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3014.4(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1463
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.8454
_cell_measurement_theta_min      3.0436
_exptl_absorpt_coefficient_mu    3.258
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1380
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_unetI/netI     0.0464
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8717
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.28
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 15.9784
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -62.00   55.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4897    0.0000  -30.0000 117

#__ type_ start__ end____ width___ exp.time_
  2 omega   18.00   61.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       18.6616 -115.0000  109.0000 43
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0226735000
_diffrn_orient_matrix_UB_12      0.0038624000
_diffrn_orient_matrix_UB_13      0.0497886000
_diffrn_orient_matrix_UB_21      0.0424152000
_diffrn_orient_matrix_UB_22      0.0072993000
_diffrn_orient_matrix_UB_23      0.0251213000
_diffrn_orient_matrix_UB_31      -0.0052455000
_diffrn_orient_matrix_UB_32      0.0424558000
_diffrn_orient_matrix_UB_33      -0.0088809000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1559
_reflns_number_total             3084
_reflns_odcompleteness_completeness 99.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_refine_diff_density_max         1.382
_refine_diff_density_min         -1.085
_refine_diff_density_rms         0.134
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         3084
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.1571
_refine_ls_R_factor_gt           0.0934
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1847P)²+2.1905P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2749
_refine_ls_wR_factor_ref         0.3360
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.12246(7) 0.58604(7) -0.07503(13) 0.1281(8) Uani 1 1 d . . .
Co1 Co 0.12835(9) 0.2500 0.2500 0.0543(5) Uani 1 2 d S . .
O1 O 0.1276(4) 0.2437(3) 0.1011(5) 0.0739(17) Uani 1 1 d . . .
O2 O 0.4923(17) 0.4511(11) 0.487(2) 0.213(13) Uani 0.48(2) 1 d PU . 1
O3 O 0.6107(18) 0.396(2) 0.386(3) 0.226(15) Uani 0.52(2) 1 d PU . 2
N1 N 0.1291(4) 0.3658(4) 0.2321(7) 0.072(2) Uani 1 1 d . . .
N2 N -0.0034(7) 0.2500 0.2500 0.066(3) Uani 1 2 d S . .
N3 N 0.2622(6) 0.2500 0.2500 0.063(2) Uani 1 2 d S . .
C1 C 0.1260(5) 0.3157(6) 0.0585(8) 0.070(2) Uani 1 1 d . . .
C2 C 0.1232(6) 0.3304(8) -0.0542(8) 0.087(3) Uani 1 1 d . . .
H2 H 0.1227 0.2872 -0.1021 0.104 Uiso 1 1 calc R . .
C3 C 0.1213(7) 0.4108(8) -0.0896(10) 0.095(4) Uani 1 1 d . . .
H3 H 0.1195 0.4201 -0.1624 0.115 Uiso 1 1 calc R . .
C4 C 0.1219(6) 0.4791(9) -0.0209(14) 0.117(5) Uani 1 1 d . . .
C5 C 0.1251(5) 0.4664(6) 0.0888(10) 0.080(3) Uani 1 1 d . . .
C6 C 0.1253(6) 0.5287(5) 0.1712(11) 0.083(3) Uani 1 1 d . . .
H6 H 0.1232 0.5837 0.1533 0.099 Uiso 1 1 calc R . .
C7 C 0.1285(7) 0.5061(6) 0.2706(12) 0.099(4) Uani 1 1 d . . .
H7 H 0.1289 0.5465 0.3226 0.119 Uiso 1 1 calc R . .
C8 C 0.1315(6) 0.4241(5) 0.3033(10) 0.086(3) Uani 1 1 d . . .
H8 H 0.1350 0.4112 0.3751 0.103 Uiso 1 1 calc R . .
C9 C 0.1267(5) 0.3849(5) 0.1239(6) 0.0552(18) Uani 1 1 d . . .
C10 C -0.0512(7) 0.2910(5) 0.3209(8) 0.082(3) Uani 1 1 d . . .
H10 H -0.0189 0.3206 0.3716 0.098 Uiso 1 1 calc R . .
C11 C -0.1442(8) 0.2934(8) 0.3256(9) 0.102(4) Uani 1 1 d . . .
H11 H -0.1748 0.3231 0.3776 0.122 Uiso 1 1 calc R . .
C12 C -0.1902(13) 0.2500 0.2500 0.118(7) Uani 1 2 d S . .
H12 H -0.2538 0.2500 0.2500 0.141 Uiso 1 2 calc SR . .
C13 C 0.3098(7) 0.2789(5) 0.3355(6) 0.068(2) Uani 1 1 d . . .
H13 H 0.2777 0.2992 0.3936 0.081 Uiso 1 1 calc R . .
C14 C 0.4006(7) 0.2789(7) 0.3380(9) 0.082(3) Uani 1 1 d . . .
H14 H 0.4326 0.2978 0.3969 0.098 Uiso 1 1 calc R . .
C15 C 0.4448(12) 0.2500 0.2500 0.147(10) Uani 1 2 d S . .
H15 H 0.5084 0.2500 0.2500 0.176 Uiso 1 2 calc SR . .


_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
Br1 C4 1.880(11) . ?
Co1 O1 1.878(6) 3 ?
Co1 O1 1.878(6) . ?
Co1 N1 1.910(7) 3 ?
Co1 N1 1.910(7) . ?
Co1 N2 1.926(10) . ?
Co1 N3 1.956(10) . ?
O1 C1 1.295(10) . ?
O2 O2 1.65(4) 5_666 ?
N1 C8 1.310(12) . ?
N1 C9 1.398(11) . ?
N2 C10 1.318(10) . ?
N2 C10 1.318(10) 3 ?
N3 C13 1.367(9) . ?
N3 C13 1.367(9) 3 ?
C1 C2 1.441(14) . ?
C1 C9 1.402(12) . ?
C2 H2 0.9300 . ?
C2 C3 1.390(16) . ?
C3 H3 0.9300 . ?
C3 C4 1.41(2) . ?
C4 C5 1.398(18) . ?
C5 C6 1.455(15) . ?
C5 C9 1.405(13) . ?
C6 H6 0.9300 . ?
C6 C7 1.307(16) . ?
C7 H7 0.9300 . ?
C7 C8 1.406(13) . ?
C8 H8 0.9300 . ?
C10 H10 0.9300 . ?
C10 C11 1.362(14) . ?
C11 H11 0.9300 . ?
C11 C12 1.365(15) . ?
C12 C11 1.365(15) 3 ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C13 C14 1.326(14) . ?
C14 H14 0.9300 . ?
C14 C15 1.368(12) . ?
C15 C14 1.368(12) 3 ?
C15 H15 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
O1 Co1 O1 179.4(3) 3 . ?
O1 Co1 N1 86.4(3) 3 3 ?
O1 Co1 N1 93.6(3) . 3 ?
O1 Co1 N1 93.6(3) 3 . ?
O1 Co1 N1 86.4(3) . . ?
O1 Co1 N2 89.68(17) 3 . ?
O1 Co1 N2 89.68(17) . . ?
O1 Co1 N3 90.32(17) . . ?
O1 Co1 N3 90.32(17) 3 . ?
N1 Co1 N1 179.3(4) 3 . ?
N1 Co1 N2 90.33(18) . . ?
N1 Co1 N2 90.33(18) 3 . ?
N1 Co1 N3 89.67(18) 3 . ?
N1 Co1 N3 89.67(18) . . ?
N2 Co1 N3 180.0 . . ?
C1 O1 Co1 111.3(5) . . ?
C8 N1 Co1 130.0(7) . . ?
C8 N1 C9 120.3(8) . . ?
C9 N1 Co1 109.7(6) . . ?
C10 N2 Co1 122.0(6) . . ?
C10 N2 Co1 122.0(6) 3 . ?
C10 N2 C10 116.1(13) . 3 ?
C13 N3 Co1 120.6(5) . . ?
C13 N3 Co1 120.6(5) 3 . ?
C13 N3 C13 118.8(11) . 3 ?
O1 C1 C2 124.1(9) . . ?
O1 C1 C9 119.6(8) . . ?
C9 C1 C2 116.3(9) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 C1 118.3(11) . . ?
C3 C2 H2 120.8 . . ?
C2 C3 H3 118.2 . . ?
C2 C3 C4 123.6(11) . . ?
C4 C3 H3 118.2 . . ?
C3 C4 Br1 121.0(11) . . ?
C5 C4 Br1 119.8(13) . . ?
C5 C4 C3 119.1(10) . . ?
C4 C5 C6 126.9(11) . . ?
C4 C5 C9 116.9(11) . . ?
C9 C5 C6 116.2(10) . . ?
C5 C6 H6 120.5 . . ?
C7 C6 C5 119.0(9) . . ?
C7 C6 H6 120.5 . . ?
C6 C7 H7 118.3 . . ?
C6 C7 C8 123.5(12) . . ?
C8 C7 H7 118.3 . . ?
N1 C8 C7 119.7(11) . . ?
N1 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
N1 C9 C1 113.0(7) . . ?
N1 C9 C5 121.3(8) . . ?
C1 C9 C5 125.7(9) . . ?
N2 C10 H10 117.5 . . ?
N2 C10 C11 124.9(11) . . ?
C11 C10 H10 117.5 . . ?
C10 C11 H11 121.7 . . ?
C10 C11 C12 116.5(13) . . ?
C12 C11 H11 121.7 . . ?
C11 C12 C11 121.0(17) . 3 ?
C11 C12 H12 119.5 3 . ?
C11 C12 H12 119.5 . . ?
N3 C13 H13 119.1 . . ?
C14 C13 N3 121.9(9) . . ?
C14 C13 H13 119.1 . . ?
C13 C14 H14 121.5 . . ?
C13 C14 C15 117.0(12) . . ?
C15 C14 H14 121.5 . . ?
C14 C15 C14 123.6(16) . 3 ?
C14 C15 H15 118.2 . . ?
C14 C15 H15 118.2 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
Br1 C4 C5 C6 2.7(13) . . . . ?
Br1 C4 C5 C9 -178.6(5) . . . . ?
Co1 O1 C1 C2 -178.7(7) . . . . ?
Co1 O1 C1 C9 1.1(8) . . . . ?
Co1 N1 C8 C7 -178.0(6) . . . . ?
Co1 N1 C9 C1 -1.1(7) . . . . ?
Co1 N1 C9 C5 178.9(5) . . . . ?
Co1 N2 C10 C11 -179.8(7) . . . . ?
Co1 N3 C13 C14 179.4(7) . . . . ?
O1 Co1 O1 C1 89.0(5) 3 . . . ?
O1 Co1 N1 C8 -178.7(7) . . . . ?
O1 Co1 N1 C8 2.0(7) 3 . . . ?
O1 Co1 N1 C9 1.3(5) . . . . ?
O1 Co1 N1 C9 -178.0(5) 3 . . . ?
O1 Co1 N2 C10 -146.2(4) . . . . ?
O1 Co1 N2 C10 33.8(4) 3 . . . ?
O1 Co1 N2 C10 -146.2(4) 3 . . 3 ?
O1 Co1 N2 C10 33.8(4) . . . 3 ?
O1 Co1 N3 C13 159.4(4) 3 . . 3 ?
O1 Co1 N3 C13 -20.6(4) . . . 3 ?
O1 Co1 N3 C13 159.4(4) . . . . ?
O1 Co1 N3 C13 -20.6(4) 3 . . . ?
O1 C1 C2 C3 179.7(7) . . . . ?
O1 C1 C9 N1 0.0(10) . . . . ?
O1 C1 C9 C5 180.0(7) . . . . ?
N1 Co1 O1 C1 -1.4(5) . . . . ?
N1 Co1 O1 C1 179.3(5) 3 . . . ?
N1 Co1 N1 C8 -88.3(7) 3 . . . ?
N1 Co1 N1 C9 91.7(5) 3 . . . ?
N1 Co1 N2 C10 -59.8(5) 3 . . 3 ?
N1 Co1 N2 C10 -59.8(5) . . . . ?
N1 Co1 N2 C10 120.2(5) . . . 3 ?
N1 Co1 N2 C10 120.2(5) 3 . . . ?
N1 Co1 N3 C13 -107.0(5) 3 . . . ?
N1 Co1 N3 C13 73.0(5) 3 . . 3 ?
N1 Co1 N3 C13 -107.0(5) . . . 3 ?
N1 Co1 N3 C13 73.0(5) . . . . ?
N2 Co1 O1 C1 89.0(5) . . . . ?
N2 Co1 N1 C8 91.7(7) . . . . ?
N2 Co1 N1 C9 -88.3(5) . . . . ?
N2 Co1 N3 C13 0(100) . . . 3 ?
N2 Co1 N3 C13 0(100) . . . . ?
N2 C10 C11 C12 -0.4(12) . . . . ?
N3 Co1 O1 C1 -91.0(5) . . . . ?
N3 Co1 N1 C8 -88.3(7) . . . . ?
N3 Co1 N1 C9 91.7(5) . . . . ?
N3 Co1 N2 C10 0(100) . . . . ?
N3 Co1 N2 C10 0(100) . . . 3 ?
N3 C13 C14 C15 1.2(12) . . . . ?
C1 C2 C3 C4 0.0(15) . . . . ?
C2 C1 C9 N1 179.8(7) . . . . ?
C2 C1 C9 C5 -0.2(12) . . . . ?
C2 C3 C4 Br1 178.3(7) . . . . ?
C2 C3 C4 C5 0.4(15) . . . . ?
C3 C4 C5 C6 -179.3(8) . . . . ?
C3 C4 C5 C9 -0.6(13) . . . . ?
C4 C5 C6 C7 180.0(10) . . . . ?
C4 C5 C9 N1 -179.5(8) . . . . ?
C4 C5 C9 C1 0.6(11) . . . . ?
C5 C6 C7 C8 -0.3(15) . . . . ?
C6 C5 C9 N1 -0.6(10) . . . . ?
C6 C5 C9 C1 179.4(7) . . . . ?
C6 C7 C8 N1 -1.4(15) . . . . ?
C8 N1 C9 C1 178.9(7) . . . . ?
C8 N1 C9 C5 -1.1(10) . . . . ?
C9 N1 C8 C7 2.0(12) . . . . ?
C9 C1 C2 C3 0.0(13) . . . . ?
C9 C5 C6 C7 1.2(12) . . . . ?
C10 N2 C10 C11 0.2(7) 3 . . . ?
C10 C11 C12 C11 0.2(6) . . . 3 ?
C13 N3 C13 C14 -0.6(7) 3 . . . ?
C13 C14 C15 C14 -0.6(6) . . . 3 ?

####################################################################### 
# 
# 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_141017
_database_code_depnum_ccdc_archive 'CCDC 1438498'
_audit_update_record             
;
2015-11-24 deposited with the CCDC.
2016-04-01 downloaded from the CCDC.
;
_audit_creation_date             2015-11-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C28 H20 Co N6 O6, 2(C2 H2 O)'
_chemical_formula_sum            'C32 H32 Co N6 O8'
_chemical_formula_weight         687.57
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z+1/2'
3 'x+1/2, y+1/2, z'
4 '-x+1/2, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x, -y, z-1/2'
7 '-x+1/2, -y+1/2, -z'
8 'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   17.880(4)
_cell_length_b                   13.110(3)
_cell_length_c                   14.440(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.47(3)
_cell_angle_gamma                90.00
_cell_volume                     3127.9(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3752
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.200
_cell_measurement_theta_min      2.483
_exptl_absorpt_coefficient_mu    0.611
_exptl_absorpt_correction_T_max  0.9140
_exptl_absorpt_correction_T_min  0.7749
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1428
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16985
_diffrn_reflns_theta_full        26.34
_diffrn_reflns_theta_max         26.34
_diffrn_reflns_theta_min         1.98
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                2406
_reflns_number_total             3110
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT v8.27A (Bruker, 2012)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.723
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.096
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.155
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3110
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1138
_refine_ls_R_factor_gt           0.0943
_refine_ls_restrained_S_all      1.159
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0893P)²+22.6178P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2480
_refine_ls_wR_factor_ref         0.2596
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 O4-C15 = C15-C16
 1.45 with sigma of 0.02
 O4-C16
 2.5 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
3.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C12(H12), C3(H3), C11(H11), C7(H7), C5(H5), C1(H1), C2(H2), C6(H6)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_site_symmetry_order
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Co1 Co 0.2500 0.2500 0.5000 0.0473(4) Uani 1 d . . 2 S T P
C14 C 0.1117(3) 0.1328(4) 0.4304(4) 0.0434(12) Uani 1 d . . 1 . . .
N2 N 0.1337(3) 0.2332(3) 0.4414(4) 0.0480(12) Uani 1 d . . 1 . . .
C8 C -0.0303(4) 0.1776(6) 0.3612(5) 0.0646(18) Uani 1 d . . 1 . . .
H8 H -0.0850 0.1611 0.3350 0.078 Uiso 1 calc . . 1 R . .
C12 C 0.1637(4) -0.0437(5) 0.4586(5) 0.0605(17) Uani 1 d . . 1 . . .
H12 H 0.2053 -0.0915 0.4793 0.073 Uiso 1 calc . . 1 R . .
N3 N -0.0640(4) -0.0526(6) 0.3475(5) 0.079(2) Uani 1 d . . 1 . . .
C13 C 0.1794(3) 0.0639(5) 0.4654(5) 0.0486(14) Uani 1 d . . 1 . . .
O1 O 0.2530(2) 0.1038(3) 0.5029(3) 0.0579(11) Uani 1 d . . 1 . . .
N1 N 0.2547(3) 0.2490(4) 0.3651(4) 0.0537(13) Uani 1 d . . 1 . . .
C10 C 0.0169(4) -0.0072(6) 0.3849(5) 0.0643(19) Uani 1 d . . 1 . . .
C3 C 0.2613(6) 0.2471(8) 0.1749(7) 0.090(3) Uani 1 d . . 1 . . .
H3 H 0.2633 0.2470 0.1115 0.108 Uiso 1 calc . . 1 R . .
C11 C 0.0833(4) -0.0721(5) 0.4195(5) 0.0621(17) Uani 1 d . . 1 . . .
H11 H 0.0724 -0.1417 0.4161 0.075 Uiso 1 calc . . 1 R . .
C7 C -0.0053(4) 0.2789(6) 0.3735(6) 0.0667(19) Uani 1 d . . 1 . . .
H7 H -0.0440 0.3303 0.3548 0.080 Uiso 1 calc . . 1 R . .
C5 C 0.2218(4) 0.3254(6) 0.2990(5) 0.0620(17) Uani 1 d . . 1 . . .
H5 H 0.1965 0.3789 0.3178 0.074 Uiso 1 calc . . 1 R . .
C1 C 0.2908(4) 0.1719(6) 0.3360(6) 0.0668(19) Uani 1 d . . 1 . . .
H1 H 0.3139 0.1192 0.3810 0.080 Uiso 1 calc . . 1 R . .
C2 C 0.2951(6) 0.1676(7) 0.2405(8) 0.090(3) Uani 1 d . . 1 . . .
H2 H 0.3198 0.1130 0.2223 0.108 Uiso 1 calc . . 1 R . .
C4 C 0.2245(5) 0.3266(8) 0.2039(6) 0.081(2) Uani 1 d . . 1 . . .
O2 O -0.1235(4) -0.0004(5) 0.3049(6) 0.116(3) Uani 1 d . . 1 . . .
O3 O -0.0693(4) -0.1439(6) 0.3589(6) 0.125(3) Uani 1 d . . 1 . . .
C6 C 0.0783(4) 0.3055(4) 0.4140(5) 0.0593(17) Uani 1 d . . 1 . . .
H6 H 0.0938 0.3737 0.4211 0.071 Uiso 1 calc . . 1 R . .
C9 C 0.0293(4) 0.1003(5) 0.3895(5) 0.0551(16) Uani 1 d . . 1 . . .
O4 O 0.0803(8) 0.5395(8) 0.5111(10) 0.220(6) Uani 1 d . . 1 D . .
C15 C 0.0934(16) 0.6135(14) 0.4405(12) 0.32(2) Uani 1 d . . 1 D . .
H15A H 0.0647 0.6765 0.4401 0.379 Uiso 1 calc . . 1 R . .
H15B H 0.1506 0.6291 0.4622 0.379 Uiso 1 calc . . 1 R . .
C16 C 0.064(2) 0.570(3) 0.3402(15) 0.51(4) Uani 1 d . . 1 D . .
H4 H 0.204(4) 0.394(5) 0.162(4) 0.050(17) Uiso 1 d . . 1 . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 N2 1.935(5) . ?
Co1 N2 1.935(5) 7_556 ?
Co1 O1 1.917(4) . ?
Co1 O1 1.917(4) 7_556 ?
Co1 N1 1.981(6) 7_556 ?
Co1 N1 1.981(6) . ?
C14 N2 1.366(7) . ?
C14 C13 1.437(8) . ?
C14 C9 1.428(7) . ?
N2 C6 1.317(8) . ?
C8 H8 0.9300 . ?
C8 C7 1.391(10) . ?
C8 C9 1.412(10) . ?
C12 H12 0.9300 . ?
C12 C13 1.434(8) . ?
C12 C11 1.380(9) . ?
N3 C10 1.463(8) . ?
N3 O2 1.217(10) . ?
N3 O3 1.216(9) . ?
C13 O1 1.324(7) . ?
N1 C5 1.353(9) . ?
N1 C1 1.349(9) . ?
C10 C11 1.389(10) . ?
C10 C9 1.424(10) . ?
C3 H3 0.9300 . ?
C3 C2 1.383(13) . ?
C3 C4 1.380(13) . ?
C11 H11 0.9300 . ?
C7 H7 0.9300 . ?
C7 C6 1.425(9) . ?
C5 H5 0.9300 . ?
C5 C4 1.393(11) . ?
C1 H1 0.9300 . ?
C1 C2 1.411(11) . ?
C2 H2 0.9300 . ?
C4 H4 1.06(6) . ?
C6 H6 0.9300 . ?
O4 C15 1.489(16) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.456(19) . ?

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 N2 180.00(12) 7_556 . ?
N2 Co1 N1 89.3(2) . 7_556 ?
N2 Co1 N1 90.7(2) . . ?
N2 Co1 N1 90.7(2) 7_556 7_556 ?
N2 Co1 N1 89.3(2) 7_556 . ?
O1 Co1 N2 84.96(18) 7_556 7_556 ?
O1 Co1 N2 95.04(18) 7_556 . ?
O1 Co1 N2 95.04(18) . 7_556 ?
O1 Co1 N2 84.96(18) . . ?
O1 Co1 O1 180.0(3) . 7_556 ?
O1 Co1 N1 90.2(2) 7_556 7_556 ?
O1 Co1 N1 89.8(2) 7_556 . ?
O1 Co1 N1 89.8(2) . 7_556 ?
O1 Co1 N1 90.2(2) . . ?
N1 Co1 N1 180.000(1) . 7_556 ?
N2 C14 C13 113.5(5) . . ?
N2 C14 C9 122.8(5) . . ?
C9 C14 C13 123.7(6) . . ?
C14 N2 Co1 112.0(4) . . ?
C6 N2 Co1 127.5(4) . . ?
C6 N2 C14 120.6(5) . . ?
C7 C8 H8 120.7 . . ?
C7 C8 C9 118.6(5) . . ?
C9 C8 H8 120.7 . . ?
C13 C12 H12 122.0 . . ?
C11 C12 H12 122.0 . . ?
C11 C12 C13 116.1(6) . . ?
O2 N3 C10 120.5(7) . . ?
O3 N3 C10 117.9(8) . . ?
O3 N3 O2 121.6(7) . . ?
C12 C13 C14 118.5(5) . . ?
O1 C13 C14 117.8(5) . . ?
O1 C13 C12 123.6(6) . . ?
C13 O1 Co1 111.8(4) . . ?
C5 N1 Co1 121.2(5) . . ?
C1 N1 Co1 121.1(5) . . ?
C1 N1 C5 117.7(6) . . ?
C11 C10 N3 118.1(7) . . ?
C11 C10 C9 119.6(6) . . ?
C9 C10 N3 122.3(7) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C4 C3 C2 119.7(8) . . ?
C12 C11 C10 126.5(6) . . ?
C12 C11 H11 116.7 . . ?
C10 C11 H11 116.7 . . ?
C8 C7 H7 119.3 . . ?
C8 C7 C6 121.4(6) . . ?
C6 C7 H7 119.3 . . ?
N1 C5 H5 118.8 . . ?
N1 C5 C4 122.3(8) . . ?
C4 C5 H5 118.8 . . ?
N1 C1 H1 118.5 . . ?
N1 C1 C2 123.1(8) . . ?
C2 C1 H1 118.5 . . ?
C3 C2 C1 117.8(8) . . ?
C3 C2 H2 121.1 . . ?
C1 C2 H2 121.1 . . ?
C3 C4 C5 119.4(9) . . ?
C3 C4 H4 124(3) . . ?
C5 C4 H4 116(3) . . ?
N2 C6 C7 119.8(5) . . ?
N2 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C8 C9 C14 116.8(6) . . ?
C8 C9 C10 127.6(6) . . ?
C10 C9 C14 115.6(6) . . ?
O4 C15 H15A 109.8 . . ?
O4 C15 H15B 109.8 . . ?
H15A C15 H15B 108.2 . . ?
C16 C15 O4 109.5(17) . . ?
C16 C15 H15A 109.8 . . ?
C16 C15 H15B 109.8 . . ?

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
Co1 N2 C6 C7 -178.9(5) . . . . ?
Co1 N1 C5 C4 179.8(5) . . . . ?
Co1 N1 C1 C2 179.5(6) . . . . ?
C14 N2 C6 C7 0.7(10) . . . . ?
C14 C13 O1 Co1 -0.3(7) . . . . ?
N2 Co1 N2 C14 -174(100) 7_556 . . . ?
N2 Co1 N2 C6 6(53) 7_556 . . . ?
N2 Co1 O1 C13 0.5(4) . . . . ?
N2 Co1 O1 C13 -179.5(4) 7_556 . . . ?
N2 Co1 N1 C5 66.9(4) . . . . ?
N2 Co1 N1 C5 -113.1(4) 7_556 . . . ?
N2 Co1 N1 C1 67.0(5) 7_556 . . . ?
N2 Co1 N1 C1 -113.0(5) . . . . ?
N2 C14 C13 C12 179.4(6) . . . . ?
N2 C14 C13 O1 -0.2(8) . . . . ?
N2 C14 C9 C8 -0.7(9) . . . . ?
N2 C14 C9 C10 -178.9(6) . . . . ?
C8 C7 C6 N2 -0.5(12) . . . . ?
C12 C13 O1 Co1 -179.8(5) . . . . ?
N3 C10 C11 C12 -179.1(6) . . . . ?
N3 C10 C9 C14 178.3(6) . . . . ?
N3 C10 C9 C8 0.4(11) . . . . ?
C13 C14 N2 Co1 0.6(6) . . . . ?
C13 C14 N2 C6 -179.1(6) . . . . ?
C13 C14 C9 C8 178.1(6) . . . . ?
C13 C14 C9 C10 0.0(9) . . . . ?
C13 C12 C11 C10 1.3(11) . . . . ?
O1 Co1 N2 C14 -0.6(4) . . . . ?
O1 Co1 N2 C14 179.4(4) 7_556 . . . ?
O1 Co1 N2 C6 179.0(6) . . . . ?
O1 Co1 N2 C6 -1.0(6) 7_556 . . . ?
O1 Co1 O1 C13 26(3) 7_556 . . . ?
O1 Co1 N1 C5 151.9(4) . . . . ?
O1 Co1 N1 C5 -28.1(4) 7_556 . . . ?
O1 Co1 N1 C1 -28.0(5) . . . . ?
O1 Co1 N1 C1 152.0(5) 7_556 . . . ?
N1 Co1 N2 C14 -90.5(4) 7_556 . . . ?
N1 Co1 N2 C14 89.5(4) . . . . ?
N1 Co1 N2 C6 -90.8(6) . . . . ?
N1 Co1 N2 C6 89.2(6) 7_556 . . . ?
N1 Co1 O1 C13 -90.2(4) . . . . ?
N1 Co1 O1 C13 89.8(4) 7_556 . . . ?
N1 Co1 N1 C5 5(100) 7_556 . . . ?
N1 Co1 N1 C1 -175(100) 7_556 . . . ?
N1 C5 C4 C3 0.5(11) . . . . ?
N1 C1 C2 C3 0.8(12) . . . . ?
C11 C12 C13 C14 -1.0(9) . . . . ?
C11 C12 C13 O1 178.6(6) . . . . ?
C11 C10 C9 C14 0.2(10) . . . . ?
C11 C10 C9 C8 -177.7(7) . . . . ?
C7 C8 C9 C14 0.9(10) . . . . ?
C7 C8 C9 C10 178.8(7) . . . . ?
C5 N1 C1 C2 -0.4(10) . . . . ?
C1 N1 C5 C4 -0.3(9) . . . . ?
C2 C3 C4 C5 -0.1(12) . . . . ?
C4 C3 C2 C1 -0.5(13) . . . . ?
O2 N3 C10 C11 -170.7(8) . . . . ?
O2 N3 C10 C9 11.2(11) . . . . ?
O3 N3 C10 C11 8.1(11) . . . . ?
O3 N3 C10 C9 -170.0(8) . . . . ?
C9 C14 N2 Co1 179.6(5) . . . . ?
C9 C14 N2 C6 -0.1(9) . . . . ?
C9 C14 C13 C12 0.4(9) . . . . ?
C9 C14 C13 O1 -179.2(6) . . . . ?
C9 C8 C7 C6 -0.3(11) . . . . ?
C9 C10 C11 C12 -0.9(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_czf-zhr-n-co02-1001
_database_code_depnum_ccdc_archive 'CCDC 1438499'
_audit_update_record             
;
2015-11-24 deposited with the CCDC.
2016-04-01 downloaded from the CCDC.
;
_audit_creation_date             2015-11-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         
'C28 H24 Co N6 O2, 0.13(C16 O16), 0.5(C4), 0.25(O)'
_chemical_formula_sum            'C32 H24 Co N6 O4.25'
_chemical_formula_weight         619.50
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      tetragonal
_space_group_IT_number           126
_space_group_name_H-M_alt        'P 4/n n c'
_space_group_name_Hall           '-P 4a 2bc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-y+1/2, x, z'
3 '-x+1/2, -y+1/2, z'
4 'y, -x+1/2, z'
5 'x, -y+1/2, -z+1/2'
6 '-x+1/2, y, -z+1/2'
7 'y, x, -z+1/2'
8 '-y+1/2, -x+1/2, -z+1/2'
9 '-x, -y, -z'
10 'y-1/2, -x, -z'
11 'x-1/2, y-1/2, -z'
12 '-y, x-1/2, -z'
13 '-x, y-1/2, z-1/2'
14 'x-1/2, -y, z-1/2'
15 '-y, -x, z-1/2'
16 'y-1/2, x-1/2, z-1/2'

_cell_length_a                   17.9171(8)
_cell_length_b                   17.9171(8)
_cell_length_c                   17.1784(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     5514.6(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2215
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.7686
_cell_measurement_theta_min      2.8571
_exptl_absorpt_coefficient_mu    0.674
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70819
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2552
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0693
_diffrn_reflns_av_unetI/netI     0.0471
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15194
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.87
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 15.9784
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -38.00   50.00   0.5000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.6216   57.0000  150.0000 176

#__ type_ start__ end____ width___ exp.time_
  2 omega  -59.00  -18.00   0.5000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.6216  101.0000  123.0000 82

#__ type_ start__ end____ width___ exp.time_
  3 omega   21.00   47.00   0.5000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7935  -19.0000   60.0000 52
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0361054000
_diffrn_orient_matrix_UB_12      0.0109979000
_diffrn_orient_matrix_UB_13      -0.0123692000
_diffrn_orient_matrix_UB_21      0.0143474000
_diffrn_orient_matrix_UB_22      0.0084521000
_diffrn_orient_matrix_UB_23      -0.0374238000
_diffrn_orient_matrix_UB_31      -0.0074646000
_diffrn_orient_matrix_UB_32      -0.0370387000
_diffrn_orient_matrix_UB_33      -0.0122248000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1686
_reflns_number_total             2779
_reflns_odcompleteness_completeness 97.12
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         1.737
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.095
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2779
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1187
_refine_ls_R_factor_gt           0.0793
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1315P)²+11.8995P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2405
_refine_ls_wR_factor_ref         0.2728
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2AA(H2AA), C7AA(H7AA), C5(H5), C6(H6), C1AA(H1AA), C10(H10), C11(H11),
 C12(H12), C13(H13), C14(H14)
2.b X=CH2 refined with riding coordinates:
 N2(H2A,H2B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_site_symmetry_order
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Co1 Co 0.5000 0.5000 0.5000 0.0365(4) Uani 1 d . . 2 S T P
O2AA O 0.5478(2) 0.50828(19) 0.4031(2) 0.0493(10) Uani 1 d . . 1 . . .
N1 N 0.5362(2) 0.3961(2) 0.4991(2) 0.0413(10) Uani 1 d . . 1 . . .
N2 N 0.4913(3) 0.3487(3) 0.6155(3) 0.0650(15) Uani 1 d . . 1 . . .
H2A H 0.4704 0.3908 0.6258 0.078 Uiso 1 calc . . 1 R . .
H2B H 0.4874 0.3122 0.6477 0.078 Uiso 1 calc . . 1 R . .
N3 N 0.4081(2) 0.4685(2) 0.4464(3) 0.0455(11) Uani 1 d . . 1 . . .
C4AA C 0.5293(3) 0.3402(3) 0.5501(3) 0.0508(14) Uani 1 d . . 1 . . .
C2AA C 0.5648(4) 0.2698(3) 0.5340(4) 0.0658(18) Uani 1 d . . 1 . . .
H2AA H 0.5614 0.2314 0.5702 0.079 Uiso 1 calc . . 1 R . .
C7AA C 0.6025(4) 0.2587(3) 0.4677(5) 0.073(2) Uani 1 d . . 1 . . .
H7AA H 0.6249 0.2127 0.4586 0.088 Uiso 1 calc . . 1 R . .
C6AA C 0.6088(3) 0.3158(3) 0.4114(4) 0.0593(16) Uani 1 d . . 1 . . .
C5 C 0.6462(4) 0.3100(4) 0.3400(5) 0.082(2) Uani 1 d . . 1 . . .
H5 H 0.6701 0.2658 0.3267 0.098 Uiso 1 calc . . 1 R . .
C6 C 0.6475(5) 0.3689(5) 0.2903(5) 0.087(2) Uani 1 d . . 1 . . .
H6 H 0.6709 0.3639 0.2422 0.105 Uiso 1 calc . . 1 R . .
C1AA C 0.6146(4) 0.4365(4) 0.3101(4) 0.0706(18) Uani 1 d . . 1 . . .
H1AA H 0.6173 0.4766 0.2759 0.085 Uiso 1 calc . . 1 R . .
C8 C 0.5787(3) 0.4445(3) 0.3791(3) 0.0485(13) Uani 1 d . . 1 . . .
C9 C 0.5748(3) 0.3833(3) 0.4307(3) 0.0448(12) Uani 1 d . . 1 . . .
C10 C 0.3600(3) 0.4215(3) 0.4798(4) 0.0602(16) Uani 1 d . . 1 . . .
H10 H 0.3693 0.4050 0.5302 0.072 Uiso 1 calc . . 1 R . .
C11 C 0.2971(4) 0.3967(4) 0.4420(5) 0.083(2) Uani 1 d . . 1 . . .
H11 H 0.2653 0.3629 0.4662 0.100 Uiso 1 calc . . 1 R . .
C12 C 0.2814(5) 0.4217(5) 0.3694(6) 0.097(3) Uani 1 d . . 1 . . .
H12 H 0.2391 0.4052 0.3431 0.116 Uiso 1 calc . . 1 R . .
C13 C 0.3291(5) 0.4715(5) 0.3357(5) 0.087(2) Uani 1 d . . 1 . . .
H13 H 0.3193 0.4903 0.2863 0.105 Uiso 1 calc . . 1 R . .
C14 C 0.3915(4) 0.4935(4) 0.3755(4) 0.0649(17) Uani 1 d . . 1 . . .
H14 H 0.4238 0.5274 0.3520 0.078 Uiso 1 calc . . 1 R . .
O1AA O 0.6227(7) 0.6227(7) 0.2500 0.243(8) Uani 1 d . . 2 S T P
O1 O 0.4472(5) 0.2500 0.7500 0.102(3) Uani 1 d . . 2 S T P
C1 C 0.6000(11) 0.6983(8) 0.181(2) 0.281(16) Uani 1 d . . 1 . . .
C0AA C 0.700(5) 0.729(11) 0.116(3) 0.60(7) Uani 1 d . . 1 . . .
O0AA O 0.2500 0.2500 0.2500 0.175(10) Uani 1 d . . 8 S T P


_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 O2AA 1.878(4) 9_666 ?
Co1 O2AA 1.878(4) . ?
Co1 N1 1.971(4) . ?
Co1 N1 1.971(4) 9_666 ?
Co1 N3 1.969(4) . ?
Co1 N3 1.969(4) 9_666 ?
O2AA C8 1.335(6) . ?
N1 C4AA 1.337(7) . ?
N1 C9 1.382(7) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N2 C4AA 1.324(8) . ?
N3 C10 1.335(7) . ?
N3 C14 1.331(7) . ?
C4AA C2AA 1.439(8) . ?
C2AA H2AA 0.9300 . ?
C2AA C7AA 1.339(10) . ?
C7AA H7AA 0.9300 . ?
C7AA C6AA 1.413(10) . ?
C6AA C5 1.400(10) . ?
C6AA C9 1.394(8) . ?
C5 H5 0.9300 . ?
C5 C6 1.358(11) . ?
C6 H6 0.9300 . ?
C6 C1AA 1.390(10) . ?
C1AA H1AA 0.9300 . ?
C1AA C8 1.355(8) . ?
C8 C9 1.412(8) . ?
C10 H10 0.9300 . ?
C10 C11 1.375(9) . ?
C11 H11 0.9300 . ?
C11 C12 1.354(11) . ?
C12 H12 0.9300 . ?
C12 C13 1.365(12) . ?
C13 H13 0.9300 . ?
C13 C14 1.369(9) . ?
C14 H14 0.9300 . ?
O1AA C1 1.85(3) 7 ?
O1AA C1 1.85(3) . ?
O1 C1 1.73(3) 13_656 ?
O1 C1 1.73(3) 9_666 ?
C1 O1 1.73(3) 9_666 ?
C0AA C0AA 1.95(14) 3_665 ?
C0AA C0AA 1.38(10) 4_565 ?
C0AA C0AA 1.38(10) 2_655 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2AA Co1 O2AA 180.000(1) 9_666 . ?
O2AA Co1 N1 94.76(17) . 9_666 ?
O2AA Co1 N1 85.24(17) . . ?
O2AA Co1 N1 85.24(17) 9_666 9_666 ?
O2AA Co1 N1 94.76(17) 9_666 . ?
O2AA Co1 N3 89.41(17) 9_666 9_666 ?
O2AA Co1 N3 89.41(17) . . ?
O2AA Co1 N3 90.59(17) 9_666 . ?
O2AA Co1 N3 90.59(17) . 9_666 ?
N1 Co1 N1 180.0(2) . 9_666 ?
N3 Co1 N1 90.06(16) . . ?
N3 Co1 N1 89.94(16) 9_666 . ?
N3 Co1 N1 89.94(16) . 9_666 ?
N3 Co1 N1 90.06(16) 9_666 9_666 ?
N3 Co1 N3 180.0 9_666 . ?
C8 O2AA Co1 113.3(3) . . ?
C4AA N1 Co1 132.2(4) . . ?
C4AA N1 C9 118.6(4) . . ?
C9 N1 Co1 109.2(3) . . ?
H2A N2 H2B 120.0 . . ?
C4AA N2 H2A 120.0 . . ?
C4AA N2 H2B 120.0 . . ?
C10 N3 Co1 121.3(4) . . ?
C14 N3 Co1 121.2(4) . . ?
C14 N3 C10 117.5(5) . . ?
N1 C4AA C2AA 119.3(6) . . ?
N2 C4AA N1 121.2(5) . . ?
N2 C4AA C2AA 119.5(5) . . ?
C4AA C2AA H2AA 119.4 . . ?
C7AA C2AA C4AA 121.1(6) . . ?
C7AA C2AA H2AA 119.4 . . ?
C2AA C7AA H7AA 119.5 . . ?
C2AA C7AA C6AA 120.9(6) . . ?
C6AA C7AA H7AA 119.5 . . ?
C5 C6AA C7AA 125.7(6) . . ?
C9 C6AA C7AA 115.5(6) . . ?
C9 C6AA C5 118.8(6) . . ?
C6AA C5 H5 119.9 . . ?
C6 C5 C6AA 120.1(6) . . ?
C6 C5 H5 119.9 . . ?
C5 C6 H6 119.5 . . ?
C5 C6 C1AA 121.0(7) . . ?
C1AA C6 H6 119.5 . . ?
C6 C1AA H1AA 119.7 . . ?
C8 C1AA C6 120.6(7) . . ?
C8 C1AA H1AA 119.7 . . ?
O2AA C8 C1AA 123.9(6) . . ?
O2AA C8 C9 116.8(5) . . ?
C1AA C8 C9 119.3(6) . . ?
N1 C9 C6AA 124.4(5) . . ?
N1 C9 C8 115.4(4) . . ?
C6AA C9 C8 120.2(5) . . ?
N3 C10 H10 119.0 . . ?
N3 C10 C11 122.0(6) . . ?
C11 C10 H10 119.0 . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 119.9(7) . . ?
C12 C11 H11 120.0 . . ?
C11 C12 H12 120.8 . . ?
C11 C12 C13 118.5(7) . . ?
C13 C12 H12 120.8 . . ?
C12 C13 H13 120.4 . . ?
C12 C13 C14 119.2(7) . . ?
C14 C13 H13 120.4 . . ?
N3 C14 C13 122.8(7) . . ?
N3 C14 H14 118.6 . . ?
C13 C14 H14 118.6 . . ?
C1 O1AA C1 137.6(15) 7 . ?
C1 O1 C1 121.6(13) 9_666 13_656 ?
O1 C1 O1AA 93.2(17) 9_666 . ?
C0AA C0AA C0AA 45.000(8) 2_655 3_665 ?
C0AA C0AA C0AA 90.00(2) 2_655 4_565 ?
C0AA C0AA C0AA 45.00(2) 4_565 3_665 ?

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
Co1 O2AA C8 C1AA 178.4(5) . . . . ?
Co1 O2AA C8 C9 -3.6(6) . . . . ?
Co1 N1 C4AA N2 1.3(8) . . . . ?
Co1 N1 C4AA C2AA -178.0(4) . . . . ?
Co1 N1 C9 C6AA 179.1(4) . . . . ?
Co1 N1 C9 C8 -0.5(5) . . . . ?
Co1 N3 C10 C11 -177.4(5) . . . . ?
Co1 N3 C14 C13 178.4(6) . . . . ?
O2AA Co1 O2AA C8 -104(100) 9_666 . . . ?
O2AA Co1 N1 C4AA -0.5(5) 9_666 . . . ?
O2AA Co1 N1 C4AA 179.5(5) . . . . ?
O2AA Co1 N1 C9 -1.1(3) . . . . ?
O2AA Co1 N1 C9 178.9(3) 9_666 . . . ?
O2AA Co1 N3 C10 148.8(4) . . . . ?
O2AA Co1 N3 C10 -31.2(4) 9_666 . . . ?
O2AA Co1 N3 C14 148.7(5) 9_666 . . . ?
O2AA Co1 N3 C14 -31.3(5) . . . . ?
O2AA C8 C9 N1 2.7(7) . . . . ?
O2AA C8 C9 C6AA -177.0(5) . . . . ?
N1 Co1 O2AA C8 2.6(4) . . . . ?
N1 Co1 O2AA C8 -177.4(4) 9_666 . . . ?
N1 Co1 N1 C4AA -64(3) 9_666 . . . ?
N1 Co1 N1 C9 116(3) 9_666 . . . ?
N1 Co1 N3 C10 63.6(4) . . . . ?
N1 Co1 N3 C10 -116.4(4) 9_666 . . . ?
N1 Co1 N3 C14 -116.6(4) . . . . ?
N1 Co1 N3 C14 63.4(4) 9_666 . . . ?
N1 C4AA C2AA C7AA -2.0(9) . . . . ?
N2 C4AA C2AA C7AA 178.7(6) . . . . ?
N3 Co1 O2AA C8 -87.6(4) . . . . ?
N3 Co1 O2AA C8 92.4(4) 9_666 . . . ?
N3 Co1 N1 C4AA 88.9(5) 9_666 . . . ?
N3 Co1 N1 C4AA -91.1(5) . . . . ?
N3 Co1 N1 C9 -91.7(3) 9_666 . . . ?
N3 Co1 N1 C9 88.3(3) . . . . ?
N3 Co1 N3 C10 4(100) 9_666 . . . ?
N3 Co1 N3 C14 -176(100) 9_666 . . . ?
N3 C10 C11 C12 -1.8(11) . . . . ?
C4AA N1 C9 C6AA -1.3(7) . . . . ?
C4AA N1 C9 C8 179.0(5) . . . . ?
C4AA C2AA C7AA C6AA 0.0(10) . . . . ?
C2AA C7AA C6AA C5 -179.4(6) . . . . ?
C2AA C7AA C6AA C9 1.3(9) . . . . ?
C7AA C6AA C5 C6 179.3(7) . . . . ?
C7AA C6AA C9 N1 -0.7(8) . . . . ?
C7AA C6AA C9 C8 178.9(5) . . . . ?
C6AA C5 C6 C1AA 2.5(12) . . . . ?
C5 C6AA C9 N1 180.0(5) . . . . ?
C5 C6AA C9 C8 -0.4(8) . . . . ?
C5 C6 C1AA C8 -1.7(12) . . . . ?
C6 C1AA C8 O2AA 177.8(6) . . . . ?
C6 C1AA C8 C9 -0.2(10) . . . . ?
C1AA C8 C9 N1 -179.1(5) . . . . ?
C1AA C8 C9 C6AA 1.2(8) . . . . ?
C9 N1 C4AA N2 -178.1(5) . . . . ?
C9 N1 C4AA C2AA 2.6(7) . . . . ?
C9 C6AA C5 C6 -1.4(10) . . . . ?
C10 N3 C14 C13 -1.8(9) . . . . ?
C10 C11 C12 C13 -0.2(12) . . . . ?
C11 C12 C13 C14 1.2(13) . . . . ?
C12 C13 C14 N3 -0.2(12) . . . . ?
C14 N3 C10 C11 2.8(9) . . . . ?
C1 O1AA C1 O1 -89.2(7) 7 . . 9_666 ?

_olex2_submission_special_instructions 'No special instructions were received'
