# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_cnv413
_database_code_depnum_ccdc_archive 'CCDC 1434959'
_audit_update_record             
;
2015-11-03 deposited with the CCDC.
2016-02-02 downloaded from the CCDC.
;
_audit_creation_date             2013-01-21
_audit_creation_method           
;
  Olex2 1.2
  (compiled Dec  5 2012 16:20:19, GUI svn.r4385)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C23 H28 Cl Co N5 O3, F6 P'
_chemical_formula_sum            'C23 H28 Cl Co F6 N5 O3 P'
_chemical_formula_weight         661.85
_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'
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'
F F 0.0171 0.0103 '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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

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                   6.9686(4)
_cell_length_b                   22.9724(13)
_cell_length_c                   17.7667(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.4950(10)
_cell_angle_gamma                90.00
_cell_volume                     2825.9(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9943
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      24.94
_cell_measurement_theta_min      2.31
_exptl_absorpt_coefficient_mu    0.833
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6951
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0660 before and 0.0578 after correction.
The Ratio of minimum to maximum transmission is 0.9328.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.556
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1352
_exptl_crystal_size_max          0.162
_exptl_crystal_size_mid          0.101
_exptl_crystal_size_min          0.039
_exptl_special_details           
;
Data was collected using a BRUKER CCD (charge coupled device) based
diffractometer equipped with an Oxford low-temperature apparatus operating at
173 K.  A suitable crystal was chosen and mounted on a nylon loop using 
Paratone oil.  Data  were measured using omega and phi scans of 0.5° per frame 
for 30 s. The total number of images were based on 
results from the program COSMO where redundancy was expected to be 4 and 
completeness to 0.83Å to 100%. Cell parameters were
retrieved using APEX II software and refined using SAINT on all observed
reflections.Data reduction was performed using the SAINT software which 
corrects for Lp. Scaling and absorption corrections were applied using SADABS6 
multi-scan technique, supplied by George Sheldrick.  The structures are solved 
by the direct method using the SHELXS-97 program and refined by least squares 
method on F2, SHELXL-97, incorporated in OLEX2. 
;
_diffrn_reflns_av_R_equivalents  0.0760
_diffrn_reflns_av_unetI/netI     0.0421
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            46377
_diffrn_reflns_theta_full        25.39
_diffrn_reflns_theta_max         25.39
_diffrn_reflns_theta_min         1.45
_diffrn_ambient_temperature      173.15
_diffrn_detector_area_resol_mean 836.6
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_number_gt                3752
_reflns_number_total             5201
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'APEX2 (BRUKER, V2012.10-0, 2012)'
_computing_data_collection       'COSMO (BRUKER, V1.61, 2009)'
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_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  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.551
_refine_diff_density_min         -0.520
_refine_diff_density_rms         0.097
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         5201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0788
_refine_ls_R_factor_gt           0.0518
_refine_ls_restrained_S_all      1.043
_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)+(0.0940P)²+1.4990P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1385
_refine_ls_wR_factor_ref         0.1609
_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:
  H20 of C20, H19 of C19, H16 of C16, H21 of C21, H23 of C23, H22 of C22,
  {H5A,H5B} of C5, {H7A,H7B} of C7, H15 of C15, H13 of C13, H12 of C12, {H6A,
  H6B} of C6
 At 1.5 times of:
  H1 of O1, {H8A,H8B,H8C} of C8, {H11A,H11B,H11C} of C11, {H4A,H4B,H4C} of C4,
   {H1A,H1B,H1C} of C1
2.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C15(H15), C16(H16), C19(H19), C20(H20), C21(H21),
 C22(H22), C23(H23)
2.c Tetrahedral OH refined with riding coordinates:
 O1(H1)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C4(H4A,H4B,H4C), C8(H8A,H8B,H8C), C11(H11A,H11B,H11C)
;
_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
Co1 Co 0.44626(7) 0.35003(2) 0.26473(3) 0.02855(18) Uani 1 1 d . . .
Cl1 Cl 0.64599(13) 0.41288(4) 0.32965(6) 0.0403(3) Uani 1 1 d . . .
O1 O 0.7311(4) 0.32983(14) 0.16528(18) 0.0535(8) Uani 1 1 d . . .
H1 H 0.7270 0.2978 0.1878 0.080 Uiso 1 1 calc R . .
O2 O 0.7539(4) 0.26914(12) 0.27764(18) 0.0478(8) Uani 1 1 d . . .
O3 O -0.1069(6) 0.17078(17) 0.01488(19) 0.0734(11) Uani 1 1 d . . .
N1 N 0.5822(5) 0.36262(15) 0.1799(2) 0.0392(8) Uani 1 1 d . . .
N2 N 0.2999(5) 0.41552(13) 0.22052(19) 0.0347(7) Uani 1 1 d . . .
N3 N 0.3202(4) 0.33864(13) 0.35443(18) 0.0329(7) Uani 1 1 d . . .
N4 N 0.6067(4) 0.29046(13) 0.31066(19) 0.0335(7) Uani 1 1 d . . .
N5 N 0.2704(4) 0.29276(13) 0.20823(17) 0.0285(7) Uani 1 1 d . . .
C1 C 0.6410(8) 0.4245(2) 0.0734(3) 0.0634(14) Uani 1 1 d . . .
H1A H 0.7386 0.4539 0.0902 0.095 Uiso 1 1 calc R . .
H1B H 0.5501 0.4406 0.0325 0.095 Uiso 1 1 calc R . .
H1C H 0.7043 0.3901 0.0548 0.095 Uiso 1 1 calc R . .
C2 C 0.5343(6) 0.40770(18) 0.1382(2) 0.0414(10) Uani 1 1 d . . .
C3 C 0.3688(6) 0.43846(17) 0.1634(2) 0.0418(10) Uani 1 1 d . . .
C4 C 0.2939(8) 0.49143(19) 0.1217(3) 0.0605(14) Uani 1 1 d . . .
H4A H 0.1966 0.5102 0.1493 0.091 Uiso 1 1 calc R . .
H4B H 0.2351 0.4804 0.0709 0.091 Uiso 1 1 calc R . .
H4C H 0.4005 0.5186 0.1173 0.091 Uiso 1 1 calc R . .
C5 C 0.1303(6) 0.43807(19) 0.2533(3) 0.0473(11) Uani 1 1 d . . .
H5A H 0.0141 0.4166 0.2314 0.057 Uiso 1 1 calc R . .
H5B H 0.1121 0.4796 0.2395 0.057 Uiso 1 1 calc R . .
C6 C 0.1496(6) 0.4324(2) 0.3386(3) 0.0496(12) Uani 1 1 d . . .
H6A H 0.2722 0.4510 0.3596 0.060 Uiso 1 1 calc R . .
H6B H 0.0429 0.4542 0.3578 0.060 Uiso 1 1 calc R . .
C7 C 0.1470(6) 0.3721(2) 0.3673(3) 0.0468(11) Uani 1 1 d . . .
H7A H 0.1356 0.3731 0.4223 0.056 Uiso 1 1 calc R . .
H7B H 0.0316 0.3519 0.3421 0.056 Uiso 1 1 calc R . .
C8 C 0.3397(7) 0.2867(2) 0.4767(2) 0.0554(12) Uani 1 1 d . . .
H8A H 0.4235 0.3065 0.5168 0.083 Uiso 1 1 calc R . .
H8B H 0.3486 0.2445 0.4845 0.083 Uiso 1 1 calc R . .
H8C H 0.2058 0.2993 0.4783 0.083 Uiso 1 1 calc R . .
C9 C 0.4025(6) 0.30163(18) 0.4012(2) 0.0391(10) Uani 1 1 d . . .
C10 C 0.5710(6) 0.27204(17) 0.3762(2) 0.0385(10) Uani 1 1 d . . .
C11 C 0.6835(7) 0.2246(2) 0.4175(3) 0.0622(14) Uani 1 1 d . . .
H11A H 0.6296 0.1869 0.4004 0.093 Uiso 1 1 calc R . .
H11B H 0.6765 0.2288 0.4720 0.093 Uiso 1 1 calc R . .
H11C H 0.8186 0.2269 0.4073 0.093 Uiso 1 1 calc R . .
C12 C 0.2328(6) 0.24053(16) 0.2372(2) 0.0369(9) Uani 1 1 d . . .
H12 H 0.2967 0.2306 0.2855 0.044 Uiso 1 1 calc R . .
C13 C 0.1077(6) 0.20073(17) 0.2011(2) 0.0382(9) Uani 1 1 d . . .
H13 H 0.0855 0.1646 0.2246 0.046 Uiso 1 1 calc R . .
C14 C 0.0140(5) 0.21373(17) 0.1302(2) 0.0336(9) Uani 1 1 d . . .
C15 C 0.0548(5) 0.26730(16) 0.0994(2) 0.0336(9) Uani 1 1 d . . .
H15 H -0.0053 0.2778 0.0506 0.040 Uiso 1 1 calc R . .
C16 C 0.1806(5) 0.30497(16) 0.1387(2) 0.0315(8) Uani 1 1 d . . .
H16 H 0.2058 0.3413 0.1161 0.038 Uiso 1 1 calc R . .
C17 C -0.1182(6) 0.17278(19) 0.0830(3) 0.0440(10) Uani 1 1 d . . .
C18 C -0.2611(6) 0.13545(18) 0.1170(3) 0.0414(10) Uani 1 1 d . . .
C19 C -0.3539(7) 0.0924(2) 0.0709(3) 0.0602(13) Uani 1 1 d . . .
H19 H -0.3203 0.0864 0.0211 0.072 Uiso 1 1 calc R . .
C20 C -0.4952(8) 0.0587(2) 0.0982(4) 0.0743(17) Uani 1 1 d . . .
H20 H -0.5598 0.0294 0.0671 0.089 Uiso 1 1 calc R . .
C21 C -0.5421(8) 0.0676(2) 0.1706(4) 0.0753(18) Uani 1 1 d . . .
H21 H -0.6389 0.0443 0.1893 0.090 Uiso 1 1 calc R . .
C22 C -0.4500(8) 0.1097(2) 0.2157(3) 0.0646(14) Uani 1 1 d . . .
H22 H -0.4831 0.1153 0.2656 0.078 Uiso 1 1 calc R . .
C23 C -0.3078(7) 0.14451(18) 0.1891(3) 0.0500(12) Uani 1 1 d . . .
H23 H -0.2445 0.1739 0.2203 0.060 Uiso 1 1 calc R . .
P1 P 0.15160(18) 0.38809(5) 0.90924(7) 0.0497(3) Uani 1 1 d . . .
F1 F -0.0445(7) 0.3827(2) 0.9402(4) 0.172(3) Uani 1 1 d . . .
F2 F 0.1397(6) 0.32219(16) 0.8833(2) 0.1099(14) Uani 1 1 d . . .
F3 F 0.3523(6) 0.3925(3) 0.8832(3) 0.166(2) Uani 1 1 d . . .
F4 F 0.2490(8) 0.36670(17) 0.98857(19) 0.1213(17) Uani 1 1 d . . .
F5 F 0.1569(6) 0.45252(14) 0.9374(2) 0.1032(13) Uani 1 1 d . . .
F6 F 0.0528(9) 0.4071(2) 0.8315(2) 0.169(3) 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 Cl1 2.2336(11) . ?
Co1 N1 1.891(3) . ?
Co1 N2 1.934(3) . ?
Co1 N3 1.923(3) . ?
Co1 N4 1.893(3) . ?
Co1 N5 1.990(3) . ?
O1 H1 0.8400 . ?
O1 N1 1.331(4) . ?
O2 N4 1.331(4) . ?
O3 C17 1.223(5) . ?
N1 C2 1.295(5) . ?
N2 C3 1.284(5) . ?
N2 C5 1.470(5) . ?
N3 C7 1.470(5) . ?
N3 C9 1.278(5) . ?
N4 C10 1.289(5) . ?
N5 C12 1.343(5) . ?
N5 C16 1.350(5) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.490(6) . ?
C2 C3 1.466(6) . ?
C3 C4 1.489(6) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.511(6) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.477(6) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C8 C9 1.498(6) . ?
C9 C10 1.468(6) . ?
C10 C11 1.487(6) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12 0.9500 . ?
C12 C13 1.371(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.385(5) . ?
C14 C15 1.389(5) . ?
C14 C17 1.504(5) . ?
C15 H15 0.9500 . ?
C15 C16 1.366(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.492(6) . ?
C18 C19 1.394(6) . ?
C18 C23 1.373(6) . ?
C19 H19 0.9500 . ?
C19 C20 1.384(7) . ?
C20 H20 0.9500 . ?
C20 C21 1.378(8) . ?
C21 H21 0.9500 . ?
C21 C22 1.369(7) . ?
C22 H22 0.9500 . ?
C22 C23 1.398(6) . ?
C23 H23 0.9500 . ?
P1 F1 1.534(4) . ?
P1 F2 1.582(4) . ?
P1 F3 1.525(4) . ?
P1 F4 1.572(4) . ?
P1 F5 1.561(3) . ?
P1 F6 1.536(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
N1 Co1 Cl1 88.49(11) . . ?
N1 Co1 N2 81.13(15) . . ?
N1 Co1 N3 176.90(14) . . ?
N1 Co1 N4 97.45(15) . . ?
N1 Co1 N5 91.97(13) . . ?
N2 Co1 Cl1 88.63(10) . . ?
N2 Co1 N5 92.47(13) . . ?
N3 Co1 Cl1 88.64(10) . . ?
N3 Co1 N2 99.97(14) . . ?
N3 Co1 N5 90.87(13) . . ?
N4 Co1 Cl1 86.65(10) . . ?
N4 Co1 N2 175.11(13) . . ?
N4 Co1 N3 81.21(14) . . ?
N4 Co1 N5 92.26(12) . . ?
N5 Co1 Cl1 178.86(9) . . ?
N1 O1 H1 109.5 . . ?
O1 N1 Co1 122.7(3) . . ?
C2 N1 Co1 117.3(3) . . ?
C2 N1 O1 119.8(4) . . ?
C3 N2 Co1 114.4(3) . . ?
C3 N2 C5 123.9(3) . . ?
C5 N2 Co1 121.6(3) . . ?
C7 N3 Co1 121.2(3) . . ?
C9 N3 Co1 114.6(3) . . ?
C9 N3 C7 124.2(4) . . ?
O2 N4 Co1 121.5(3) . . ?
C10 N4 Co1 117.5(3) . . ?
C10 N4 O2 120.9(3) . . ?
C12 N5 Co1 122.2(2) . . ?
C12 N5 C16 116.5(3) . . ?
C16 N5 Co1 121.3(2) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
N1 C2 C1 122.1(4) . . ?
N1 C2 C3 111.8(4) . . ?
C3 C2 C1 126.1(4) . . ?
N2 C3 C2 114.9(4) . . ?
N2 C3 C4 126.0(4) . . ?
C2 C3 C4 119.1(4) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N2 C5 H5A 109.1 . . ?
N2 C5 H5B 109.1 . . ?
N2 C5 C6 112.5(3) . . ?
H5A C5 H5B 107.8 . . ?
C6 C5 H5A 109.1 . . ?
C6 C5 H5B 109.1 . . ?
C5 C6 H6A 108.5 . . ?
C5 C6 H6B 108.5 . . ?
H6A C6 H6B 107.5 . . ?
C7 C6 C5 115.1(4) . . ?
C7 C6 H6A 108.5 . . ?
C7 C6 H6B 108.5 . . ?
N3 C7 C6 113.2(4) . . ?
N3 C7 H7A 108.9 . . ?
N3 C7 H7B 108.9 . . ?
C6 C7 H7A 108.9 . . ?
C6 C7 H7B 108.9 . . ?
H7A C7 H7B 107.8 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C9 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
C9 C8 H8C 109.5 . . ?
N3 C9 C8 125.4(4) . . ?
N3 C9 C10 115.2(4) . . ?
C10 C9 C8 119.3(4) . . ?
N4 C10 C9 111.3(3) . . ?
N4 C10 C11 122.8(4) . . ?
C9 C10 C11 125.8(4) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N5 C12 H12 118.0 . . ?
N5 C12 C13 123.9(4) . . ?
C13 C12 H12 118.0 . . ?
C12 C13 H13 120.3 . . ?
C12 C13 C14 119.4(4) . . ?
C14 C13 H13 120.3 . . ?
C13 C14 C15 117.0(3) . . ?
C13 C14 C17 124.6(4) . . ?
C15 C14 C17 118.3(3) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.5(4) . . ?
C16 C15 H15 119.7 . . ?
N5 C16 C15 122.7(3) . . ?
N5 C16 H16 118.6 . . ?
C15 C16 H16 118.6 . . ?
O3 C17 C14 118.1(4) . . ?
O3 C17 C18 119.9(4) . . ?
C18 C17 C14 121.9(4) . . ?
C19 C18 C17 117.1(4) . . ?
C23 C18 C17 122.0(4) . . ?
C23 C18 C19 120.8(4) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 C18 119.5(5) . . ?
C20 C19 H19 120.3 . . ?
C19 C20 H20 120.1 . . ?
C21 C20 C19 119.9(5) . . ?
C21 C20 H20 120.1 . . ?
C20 C21 H21 119.8 . . ?
C22 C21 C20 120.4(5) . . ?
C22 C21 H21 119.8 . . ?
C21 C22 H22 119.7 . . ?
C21 C22 C23 120.6(5) . . ?
C23 C22 H22 119.7 . . ?
C18 C23 C22 118.8(4) . . ?
C18 C23 H23 120.6 . . ?
C22 C23 H23 120.6 . . ?
F1 P1 F2 90.5(2) . . ?
F1 P1 F4 88.0(4) . . ?
F1 P1 F5 87.2(2) . . ?
F1 P1 F6 91.1(4) . . ?
F3 P1 F1 176.6(4) . . ?
F3 P1 F2 89.7(3) . . ?
F3 P1 F4 88.6(3) . . ?
F3 P1 F5 92.6(3) . . ?
F3 P1 F6 92.3(3) . . ?
F4 P1 F2 88.0(2) . . ?
F5 P1 F2 177.5(3) . . ?
F5 P1 F4 91.0(2) . . ?
F6 P1 F2 90.4(2) . . ?
F6 P1 F4 178.1(3) . . ?
F6 P1 F5 90.6(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Co1 N1 C2 C1 175.3(3) . . . . ?
Co1 N1 C2 C3 -4.2(5) . . . . ?
Co1 N2 C3 C2 5.3(4) . . . . ?
Co1 N2 C3 C4 -175.7(3) . . . . ?
Co1 N2 C5 C6 33.3(5) . . . . ?
Co1 N3 C7 C6 -35.2(5) . . . . ?
Co1 N3 C9 C8 177.1(3) . . . . ?
Co1 N3 C9 C10 -3.5(4) . . . . ?
Co1 N4 C10 C9 1.5(4) . . . . ?
Co1 N4 C10 C11 178.7(3) . . . . ?
Co1 N5 C12 C13 177.7(3) . . . . ?
Co1 N5 C16 C15 -178.0(3) . . . . ?
Cl1 Co1 N1 O1 91.8(3) . . . . ?
Cl1 Co1 N1 C2 -83.3(3) . . . . ?
Cl1 Co1 N2 C3 82.8(3) . . . . ?
Cl1 Co1 N2 C5 -94.2(3) . . . . ?
Cl1 Co1 N3 C7 94.6(3) . . . . ?
Cl1 Co1 N3 C9 -83.5(3) . . . . ?
Cl1 Co1 N4 O2 -92.0(3) . . . . ?
Cl1 Co1 N4 C10 86.5(3) . . . . ?
Cl1 Co1 N5 C12 18(5) . . . . ?
Cl1 Co1 N5 C16 -163(4) . . . . ?
O1 N1 C2 C1 0.1(6) . . . . ?
O1 N1 C2 C3 -179.5(3) . . . . ?
O2 N4 C10 C9 -180.0(3) . . . . ?
O2 N4 C10 C11 -2.8(6) . . . . ?
O3 C17 C18 C19 10.6(7) . . . . ?
O3 C17 C18 C23 -166.2(5) . . . . ?
N1 Co1 N2 C3 -5.9(3) . . . . ?
N1 Co1 N2 C5 177.1(3) . . . . ?
N1 Co1 N3 C7 117(3) . . . . ?
N1 Co1 N3 C9 -61(3) . . . . ?
N1 Co1 N4 O2 -4.0(3) . . . . ?
N1 Co1 N4 C10 174.5(3) . . . . ?
N1 Co1 N5 C12 131.5(3) . . . . ?
N1 Co1 N5 C16 -49.3(3) . . . . ?
N1 C2 C3 N2 -0.8(5) . . . . ?
N1 C2 C3 C4 -179.9(4) . . . . ?
N2 Co1 N1 O1 -179.3(3) . . . . ?
N2 Co1 N1 C2 5.6(3) . . . . ?
N2 Co1 N3 C7 6.3(3) . . . . ?
N2 Co1 N3 C9 -171.8(3) . . . . ?
N2 Co1 N4 O2 -76.8(17) . . . . ?
N2 Co1 N4 C10 101.7(17) . . . . ?
N2 Co1 N5 C12 -147.2(3) . . . . ?
N2 Co1 N5 C16 31.9(3) . . . . ?
N2 C5 C6 C7 -68.0(5) . . . . ?
N3 Co1 N1 O1 69(3) . . . . ?
N3 Co1 N1 C2 -106(3) . . . . ?
N3 Co1 N2 C3 171.2(3) . . . . ?
N3 Co1 N2 C5 -5.8(3) . . . . ?
N3 Co1 N4 O2 178.9(3) . . . . ?
N3 Co1 N4 C10 -2.7(3) . . . . ?
N3 Co1 N5 C12 -47.2(3) . . . . ?
N3 Co1 N5 C16 131.9(3) . . . . ?
N3 C9 C10 N4 1.3(5) . . . . ?
N3 C9 C10 C11 -175.7(4) . . . . ?
N4 Co1 N1 O1 5.4(3) . . . . ?
N4 Co1 N1 C2 -169.7(3) . . . . ?
N4 Co1 N2 C3 67.6(17) . . . . ?
N4 Co1 N2 C5 -109.4(16) . . . . ?
N4 Co1 N3 C7 -178.6(3) . . . . ?
N4 Co1 N3 C9 3.4(3) . . . . ?
N4 Co1 N5 C12 34.0(3) . . . . ?
N4 Co1 N5 C16 -146.8(3) . . . . ?
N5 Co1 N1 O1 -87.1(3) . . . . ?
N5 Co1 N1 C2 97.8(3) . . . . ?
N5 Co1 N2 C3 -97.5(3) . . . . ?
N5 Co1 N2 C5 85.5(3) . . . . ?
N5 Co1 N3 C7 -86.4(3) . . . . ?
N5 Co1 N3 C9 95.5(3) . . . . ?
N5 Co1 N4 O2 88.3(3) . . . . ?
N5 Co1 N4 C10 -93.2(3) . . . . ?
N5 C12 C13 C14 0.7(6) . . . . ?
C1 C2 C3 N2 179.7(4) . . . . ?
C1 C2 C3 C4 0.6(6) . . . . ?
C3 N2 C5 C6 -143.4(4) . . . . ?
C5 N2 C3 C2 -177.8(4) . . . . ?
C5 N2 C3 C4 1.2(6) . . . . ?
C5 C6 C7 N3 69.2(5) . . . . ?
C7 N3 C9 C8 -1.0(6) . . . . ?
C7 N3 C9 C10 178.5(3) . . . . ?
C8 C9 C10 N4 -179.2(4) . . . . ?
C8 C9 C10 C11 3.8(6) . . . . ?
C9 N3 C7 C6 142.7(4) . . . . ?
C12 N5 C16 C15 1.2(5) . . . . ?
C12 C13 C14 C15 0.4(6) . . . . ?
C12 C13 C14 C17 176.6(4) . . . . ?
C13 C14 C15 C16 -0.7(6) . . . . ?
C13 C14 C17 O3 -139.1(5) . . . . ?
C13 C14 C17 C18 41.3(6) . . . . ?
C14 C15 C16 N5 -0.1(6) . . . . ?
C14 C17 C18 C19 -169.8(4) . . . . ?
C14 C17 C18 C23 13.4(7) . . . . ?
C15 C14 C17 O3 37.1(6) . . . . ?
C15 C14 C17 C18 -142.5(4) . . . . ?
C16 N5 C12 C13 -1.5(6) . . . . ?
C17 C14 C15 C16 -177.1(4) . . . . ?
C17 C18 C19 C20 -176.6(5) . . . . ?
C17 C18 C23 C22 176.8(4) . . . . ?
C18 C19 C20 C21 -0.4(9) . . . . ?
C19 C18 C23 C22 0.2(7) . . . . ?
C19 C20 C21 C22 0.1(9) . . . . ?
C20 C21 C22 C23 0.3(9) . . . . ?
C21 C22 C23 C18 -0.4(8) . . . . ?
C23 C18 C19 C20 0.3(8) . . . . ?

_contact_Crystallographer_email  staples@chemistry.msu.com
_contact_Crystallographer_name   'Richard Staples'

####################################################################### 
# 
# 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_cnv612_0m
_database_code_depnum_ccdc_archive 'CCDC 1434960'
_audit_update_record             
;
2015-11-03 deposited with the CCDC.
2016-02-02 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_CHEMW03_cnv612_0m           
;
PROBLEM: ALERT: The ratio of given/expected molecular weight as
RESPONSE: Squeeze was performed to remove serverly disordered solvent.
;
_vrf_PLAT051_cnv612_0m           
;
PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by . 19.03 %
RESPONSE: Formula used was that would be there if solvent was modelled
but since the solvent was very disordered, program squeeze was used 
to remove it.
;
_vrf_PLAT220_cnv612_0m           
;
PROBLEM: Large Non-Solvent C Ueq(max)/Ueq(min) ... 5.5 Ratio
RESPONSE: In part due to disorder and thermal vibrational motion.
;
_vrf_PLAT242_cnv612_0m           
;
PROBLEM: Low Ueq as Compared to Neighbors for ..... C17 Check
RESPONSE: In part due to disorder and thermal vibrational motion.
;
# end Validation Reply Form
_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C20 H32 Cl Co N5 O2, F6 P , C H2 Cl2'
_chemical_formula_sum            'C21 H34 Cl3 Co F6 N5 O2 P'
_chemical_melting_point          ?

_exptl_crystal_description       needle
_exptl_crystal_colour            orange

_diffrn_ambient_temperature      173(2)
_chemical_formula_weight         698.78

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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           tetragonal
_symmetry_space_group_name_H-M   'I -4'
_symmetry_int_tables_number      82
_chemical_absolute_configuration ?

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

_cell_length_a                   28.715(4)
_cell_length_b                   28.715(4)
_cell_length_c                   7.0017(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     5773.5(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9792
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      25.29
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.608
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2864
_exptl_absorpt_coefficient_mu    0.996
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6890
_exptl_absorpt_correction_T_max  0.8949
_exptl_absorpt_process_details   SADABS
_exptl_special_details           
;
Data was collected using a BRUKER CCD (charge coupled device) based
diffractometer equipped with an Oxford low-temperature apparatus operating at
173 K.  A suitable crystal was chosen and mounted on a glass fiber or nylon loop
using Paratone oil for Mo radiation and Mineral oil for Copper radiation.  Data 
were measured using omega and phi scans of 0.5° per frame 
for 30 s. The total number of images were based on 
results from the program COSMO where redundancy was expected to be 4 and 
completeness to 0.83Å to 100%. Cell parameters were
retrieved using APEX II software and refined using SAINT on all observed
reflections.Data reduction was performed using the SAINT software which 
corrects for Lp. Scaling and absorption corrections were applied using SADABS6 
multi-scan technique, supplied by George Sheldrick.  The structures are solved 
by the direct method using the SHELXS-97 program and refined by least squares 
method on F2, SHELXL-97, incorporated in SHELXTL-PC V 6.14. 
 
All H atoms were placed in calculated positions and refined using a riding
model.
C-H(aromatic) = 0.94  Å and Uiso(H) = 1.2Ueq(C)
C-H (alaphatic) = 0.99 Å and Uiso(H) = 1.2Ueq(C)
CH2 = 0.98 Å and Uiso(H) = 1.2Ueq(C)
CH3 = 0.97Å and Uiso(H) = 1.5Ueq(C)
N-H = 0.86 (0.92)Å and Uiso(H) = 1.2 Ueq(N)
O-H(alcohol) = 0.85Åand Uiso(H) = 1.2Ueq(O)
O-H(acid) = 0.82Å and Uiso(H) = 1.5Ueq(O)
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω,and/f 0.5 deg'
_diffrn_detector_area_resol_mean 836.6
_diffrn_reflns_number            5312
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0255
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.01
_diffrn_reflns_theta_max         25.37
_reflns_number_total             5312
_reflns_number_gt                4974
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'COSMO (BRUKER, V1.61, 2009)'
_computing_cell_refinement       'APEX2 (BRUKER, V2010.11-3, 2010)'
_computing_data_reduction        'SAINT (BRUKER, V7.68A, 2010)'
_computing_structure_solution    
'SHELXS (Sheldrick, Acta Cryst. A64 2008, 112-122)'
_computing_structure_refinement  
'SHELXL (Sheldrick, Acta Cryst. A64 2008, 112-122)'
_computing_molecular_graphics    
'SHELXTL (Sheldrick, Acta Cryst. A64 2008, 112-122)'
_computing_publication_material  
'SHELXTL (Sheldrick, Acta Cryst. A64 2008, 112-122)'

_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)+(0.0620P)²+2.7322P] 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   -0.012(14)
_refine_ls_number_reflns         5312
_refine_ls_number_parameters     336
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0355
_refine_ls_wR_factor_ref         0.0964
_refine_ls_wR_factor_gt          0.0946
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.017
_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 0.435349(11) 0.289227(13) 0.03249(5) 0.02776(11) Uani 1 1 d . . .
Cl1 Cl 0.42744(3) 0.35614(3) -0.12806(11) 0.03884(18) Uani 1 1 d . . .
O1 O 0.41911(8) 0.24014(9) -0.3111(3) 0.0448(5) Uani 1 1 d . . .
H1 H 0.454(3) 0.231(3) -0.285(13) 0.17(3) Uiso 1 1 d . . .
O2 O 0.50041(8) 0.25898(9) -0.2471(3) 0.0472(6) Uani 1 1 d . . .
N1 N 0.39992(8) 0.25989(9) -0.1633(4) 0.0356(6) Uani 1 1 d . . .
N2 N 0.37465(8) 0.29927(9) 0.1388(4) 0.0353(6) Uani 1 1 d . . .
N3 N 0.47224(8) 0.32194(8) 0.2164(4) 0.0323(5) Uani 1 1 d . . .
N4 N 0.49465(8) 0.28201(9) -0.0835(4) 0.0348(6) Uani 1 1 d . . .
N5 N 0.44153(8) 0.23051(9) 0.1771(4) 0.0325(5) Uani 1 1 d . . .
C1 C 0.35504(10) 0.26204(11) -0.1450(5) 0.0378(7) Uani 1 1 d . . .
C2 C 0.34107(9) 0.28511(11) 0.0319(5) 0.0401(7) Uani 1 1 d . . .
C3 C 0.32244(12) 0.24142(14) -0.2868(6) 0.0547(10) Uani 1 1 d . . .
H3A H 0.3398 0.2215 -0.3753 0.082 Uiso 1 1 calc R . .
H3B H 0.3071 0.2664 -0.3585 0.082 Uiso 1 1 calc R . .
H3C H 0.2989 0.2228 -0.2202 0.082 Uiso 1 1 calc R . .
C4 C 0.29023(11) 0.28901(14) 0.0815(7) 0.0554(10) Uani 1 1 d . . .
H4A H 0.2802 0.2607 0.1481 0.083 Uiso 1 1 calc R . .
H4B H 0.2720 0.2928 -0.0358 0.083 Uiso 1 1 calc R . .
H4C H 0.2854 0.3161 0.1644 0.083 Uiso 1 1 calc R . .
C5 C 0.36829(12) 0.32083(13) 0.3257(5) 0.0469(8) Uani 1 1 d . . .
H5A H 0.3710 0.2966 0.4258 0.056 Uiso 1 1 calc R . .
H5B H 0.3366 0.3342 0.3333 0.056 Uiso 1 1 calc R . .
C6 C 0.40379(13) 0.35905(13) 0.3640(5) 0.0495(8) Uani 1 1 d . . .
H6A H 0.4032 0.3813 0.2561 0.059 Uiso 1 1 calc R . .
H6B H 0.3943 0.3762 0.4804 0.059 Uiso 1 1 calc R . .
C7 C 0.45313(12) 0.34202(12) 0.3903(5) 0.0449(8) Uani 1 1 d . . .
H7A H 0.4730 0.3684 0.4311 0.054 Uiso 1 1 calc R . .
H7B H 0.4537 0.3183 0.4928 0.054 Uiso 1 1 calc R . .
C8 C 0.51582(10) 0.32604(10) 0.1737(5) 0.0373(7) Uani 1 1 d . . .
C9 C 0.52914(10) 0.30290(11) -0.0048(5) 0.0379(7) Uani 1 1 d . . .
C10 C 0.55130(12) 0.35097(13) 0.2915(6) 0.0560(10) Uani 1 1 d . . .
H10A H 0.5468 0.3847 0.2787 0.084 Uiso 1 1 calc R . .
H10B H 0.5826 0.3426 0.2473 0.084 Uiso 1 1 calc R . .
H10C H 0.5478 0.3420 0.4258 0.084 Uiso 1 1 calc R . .
C11 C 0.57681(11) 0.30363(15) -0.0899(6) 0.0561(10) Uani 1 1 d . . .
H11A H 0.5946 0.2768 -0.0430 0.084 Uiso 1 1 calc R . .
H11B H 0.5927 0.3325 -0.0531 0.084 Uiso 1 1 calc R . .
H11C H 0.5744 0.3020 -0.2294 0.084 Uiso 1 1 calc R . .
C12 C 0.40556(11) 0.20098(11) 0.1964(5) 0.0395(7) Uani 1 1 d . . .
H12 H 0.3776 0.2073 0.1289 0.047 Uiso 1 1 calc R . .
C13 C 0.40766(13) 0.16187(12) 0.3103(6) 0.0489(9) Uani 1 1 d . . .
H13 H 0.3811 0.1424 0.3205 0.059 Uiso 1 1 calc R . .
C14 C 0.44704(13) 0.15055(12) 0.4086(6) 0.0521(9) Uani 1 1 d . . .
C15 C 0.48486(12) 0.17998(12) 0.3813(6) 0.0493(8) Uani 1 1 d . . .
H15 H 0.5137 0.1730 0.4417 0.059 Uiso 1 1 calc R . .
C16 C 0.48135(10) 0.21874(11) 0.2691(5) 0.0410(7) Uani 1 1 d . . .
H16 H 0.5079 0.2382 0.2549 0.049 Uiso 1 1 calc R . .
C17 C 0.44920(18) 0.10850(16) 0.5414(9) 0.0828(16) Uani 1 1 d . . .
C18 C 0.4581(3) 0.1258(2) 0.7425(10) 0.140(3) Uani 1 1 d . . .
H18A H 0.4315 0.1445 0.7856 0.210 Uiso 1 1 calc R . .
H18B H 0.4863 0.1451 0.7438 0.210 Uiso 1 1 calc R . .
H18C H 0.4623 0.0992 0.8282 0.210 Uiso 1 1 calc R . .
C19 C 0.4905(3) 0.0778(2) 0.4892(14) 0.135(3) Uani 1 1 d . . .
H19A H 0.4917 0.0510 0.5756 0.202 Uiso 1 1 calc R . .
H19B H 0.5194 0.0958 0.5010 0.202 Uiso 1 1 calc R . .
H19C H 0.4871 0.0669 0.3573 0.202 Uiso 1 1 calc R . .
C20 C 0.4073(3) 0.0789(3) 0.5318(19) 0.207(6) Uani 1 1 d . . .
H20A H 0.4031 0.0676 0.4009 0.310 Uiso 1 1 calc R . .
H20B H 0.3800 0.0971 0.5700 0.310 Uiso 1 1 calc R . .
H20C H 0.4110 0.0523 0.6183 0.310 Uiso 1 1 calc R . .
P1 P 0.27435(4) 0.13088(3) 0.11014(16) 0.0530(3) Uani 1 1 d . . .
F1 F 0.25243(10) 0.08184(9) 0.0678(6) 0.1017(11) Uani 1 1 d . . .
F2 F 0.25968(16) 0.14749(19) -0.0920(7) 0.169(2) Uani 1 1 d . . .
F3 F 0.28791(15) 0.11429(17) 0.3098(5) 0.1328(14) Uani 1 1 d . . .
F4 F 0.29554(12) 0.17968(10) 0.1558(8) 0.1361(18) Uani 1 1 d . . .
F5 F 0.32259(10) 0.11488(15) 0.0381(6) 0.1220(13) Uani 1 1 d . . .
F6 F 0.22470(10) 0.14693(10) 0.1892(7) 0.1155(14) 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 N4 1.898(2) . ?
Co1 N1 1.903(3) . ?
Co1 N3 1.914(2) . ?
Co1 N2 1.917(2) . ?
Co1 N5 1.975(3) . ?
Co1 Cl1 2.2376(8) . ?
O1 N1 1.302(3) . ?
O1 H1 1.05(7) . ?
O2 N4 1.333(3) . ?
N1 C1 1.297(4) . ?
N2 C2 1.287(4) . ?
N2 C5 1.459(4) . ?
N3 C8 1.292(4) . ?
N3 C7 1.454(4) . ?
N4 C9 1.282(4) . ?
N5 C12 1.343(4) . ?
N5 C16 1.355(4) . ?
C1 C2 1.461(5) . ?
C1 C3 1.488(5) . ?
C2 C4 1.505(4) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.522(5) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.510(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.466(5) . ?
C8 C10 1.494(5) . ?
C9 C11 1.493(4) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.378(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.363(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.389(5) . ?
C14 C17 1.525(6) . ?
C15 C16 1.366(5) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C20 1.475(7) . ?
C17 C18 1.516(10) . ?
C17 C19 1.523(8) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
P1 F3 1.527(4) . ?
P1 F5 1.544(3) . ?
P1 F2 1.552(4) . ?
P1 F4 1.561(3) . ?
P1 F1 1.571(3) . ?
P1 F6 1.597(3) . ?

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 N1 97.07(11) . . ?
N4 Co1 N3 81.07(11) . . ?
N1 Co1 N3 175.97(11) . . ?
N4 Co1 N2 176.64(11) . . ?
N1 Co1 N2 81.96(11) . . ?
N3 Co1 N2 99.68(11) . . ?
N4 Co1 N5 92.62(11) . . ?
N1 Co1 N5 92.26(10) . . ?
N3 Co1 N5 91.39(10) . . ?
N2 Co1 N5 90.64(10) . . ?
N4 Co1 Cl1 88.27(8) . . ?
N1 Co1 Cl1 87.94(8) . . ?
N3 Co1 Cl1 88.43(8) . . ?
N2 Co1 Cl1 88.48(8) . . ?
N5 Co1 Cl1 179.06(8) . . ?
N1 O1 H1 112(5) . . ?
C1 N1 O1 121.3(3) . . ?
C1 N1 Co1 116.1(2) . . ?
O1 N1 Co1 122.61(19) . . ?
C2 N2 C5 124.2(3) . . ?
C2 N2 Co1 114.1(2) . . ?
C5 N2 Co1 121.7(2) . . ?
C8 N3 C7 121.5(3) . . ?
C8 N3 Co1 115.2(2) . . ?
C7 N3 Co1 123.3(2) . . ?
C9 N4 O2 120.4(3) . . ?
C9 N4 Co1 117.3(2) . . ?
O2 N4 Co1 122.21(19) . . ?
C12 N5 C16 116.3(3) . . ?
C12 N5 Co1 121.4(2) . . ?
C16 N5 Co1 122.2(2) . . ?
N1 C1 C2 112.2(3) . . ?
N1 C1 C3 122.7(3) . . ?
C2 C1 C3 125.0(3) . . ?
N2 C2 C1 115.5(3) . . ?
N2 C2 C4 124.7(3) . . ?
C1 C2 C4 119.7(3) . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N2 C5 C6 112.3(3) . . ?
N2 C5 H5A 109.1 . . ?
C6 C5 H5A 109.1 . . ?
N2 C5 H5B 109.1 . . ?
C6 C5 H5B 109.1 . . ?
H5A C5 H5B 107.9 . . ?
C7 C6 C5 114.6(3) . . ?
C7 C6 H6A 108.6 . . ?
C5 C6 H6A 108.6 . . ?
C7 C6 H6B 108.6 . . ?
C5 C6 H6B 108.6 . . ?
H6A C6 H6B 107.6 . . ?
N3 C7 C6 112.4(3) . . ?
N3 C7 H7A 109.1 . . ?
C6 C7 H7A 109.1 . . ?
N3 C7 H7B 109.1 . . ?
C6 C7 H7B 109.1 . . ?
H7A C7 H7B 107.9 . . ?
N3 C8 C9 114.1(3) . . ?
N3 C8 C10 125.2(3) . . ?
C9 C8 C10 120.7(3) . . ?
N4 C9 C8 112.1(3) . . ?
N4 C9 C11 122.9(3) . . ?
C8 C9 C11 124.9(3) . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N5 C12 C13 122.6(3) . . ?
N5 C12 H12 118.7 . . ?
C13 C12 H12 118.7 . . ?
C14 C13 C12 121.5(3) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C13 C14 C15 115.7(3) . . ?
C13 C14 C17 122.0(3) . . ?
C15 C14 C17 122.2(3) . . ?
C16 C15 C14 121.1(3) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
N5 C16 C15 122.6(3) . . ?
N5 C16 H16 118.7 . . ?
C15 C16 H16 118.7 . . ?
C20 C17 C18 111.7(8) . . ?
C20 C17 C19 106.9(6) . . ?
C18 C17 C19 106.3(6) . . ?
C20 C17 C14 113.3(4) . . ?
C18 C17 C14 108.3(4) . . ?
C19 C17 C14 110.1(5) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
F3 P1 F5 88.7(3) . . ?
F3 P1 F2 179.0(2) . . ?
F5 P1 F2 92.1(3) . . ?
F3 P1 F4 89.6(3) . . ?
F5 P1 F4 89.1(2) . . ?
F2 P1 F4 90.9(3) . . ?
F3 P1 F1 89.7(2) . . ?
F5 P1 F1 91.78(19) . . ?
F2 P1 F1 89.7(2) . . ?
F4 P1 F1 178.9(3) . . ?
F3 P1 F6 90.0(3) . . ?
F5 P1 F6 178.7(3) . . ?
F2 P1 F6 89.2(3) . . ?
F4 P1 F6 91.03(19) . . ?
F1 P1 F6 88.07(16) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N4 Co1 N1 C1 -173.1(2) . . . . ?
N3 Co1 N1 C1 -110.8(15) . . . . ?
N2 Co1 N1 C1 3.6(2) . . . . ?
N5 Co1 N1 C1 94.0(2) . . . . ?
Cl1 Co1 N1 C1 -85.1(2) . . . . ?
N4 Co1 N1 O1 4.5(2) . . . . ?
N3 Co1 N1 O1 66.8(16) . . . . ?
N2 Co1 N1 O1 -178.7(2) . . . . ?
N5 Co1 N1 O1 -88.4(2) . . . . ?
Cl1 Co1 N1 O1 92.5(2) . . . . ?
N4 Co1 N2 C2 70(2) . . . . ?
N1 Co1 N2 C2 -3.5(2) . . . . ?
N3 Co1 N2 C2 172.7(2) . . . . ?
N5 Co1 N2 C2 -95.7(2) . . . . ?
Cl1 Co1 N2 C2 84.6(2) . . . . ?
N4 Co1 N2 C5 -111(2) . . . . ?
N1 Co1 N2 C5 176.0(2) . . . . ?
N3 Co1 N2 C5 -7.8(2) . . . . ?
N5 Co1 N2 C5 83.8(2) . . . . ?
Cl1 Co1 N2 C5 -95.9(2) . . . . ?
N4 Co1 N3 C8 3.8(2) . . . . ?
N1 Co1 N3 C8 -59.0(16) . . . . ?
N2 Co1 N3 C8 -172.8(2) . . . . ?
N5 Co1 N3 C8 96.3(2) . . . . ?
Cl1 Co1 N3 C8 -84.6(2) . . . . ?
N4 Co1 N3 C7 -177.6(3) . . . . ?
N1 Co1 N3 C7 119.6(15) . . . . ?
N2 Co1 N3 C7 5.7(3) . . . . ?
N5 Co1 N3 C7 -85.2(2) . . . . ?
Cl1 Co1 N3 C7 93.9(2) . . . . ?
N1 Co1 N4 C9 171.7(2) . . . . ?
N3 Co1 N4 C9 -4.7(2) . . . . ?
N2 Co1 N4 C9 99(2) . . . . ?
N5 Co1 N4 C9 -95.7(2) . . . . ?
Cl1 Co1 N4 C9 84.0(2) . . . . ?
N1 Co1 N4 O2 -3.9(2) . . . . ?
N3 Co1 N4 O2 179.8(2) . . . . ?
N2 Co1 N4 O2 -77(2) . . . . ?
N5 Co1 N4 O2 88.8(2) . . . . ?
Cl1 Co1 N4 O2 -91.6(2) . . . . ?
N4 Co1 N5 C12 -138.7(3) . . . . ?
N1 Co1 N5 C12 -41.5(3) . . . . ?
N3 Co1 N5 C12 140.2(3) . . . . ?
N2 Co1 N5 C12 40.5(3) . . . . ?
Cl1 Co1 N5 C12 61(5) . . . . ?
N4 Co1 N5 C16 44.3(3) . . . . ?
N1 Co1 N5 C16 141.5(3) . . . . ?
N3 Co1 N5 C16 -36.9(3) . . . . ?
N2 Co1 N5 C16 -136.6(3) . . . . ?
Cl1 Co1 N5 C16 -116(5) . . . . ?
O1 N1 C1 C2 179.3(2) . . . . ?
Co1 N1 C1 C2 -3.0(3) . . . . ?
O1 N1 C1 C3 1.5(5) . . . . ?
Co1 N1 C1 C3 179.2(2) . . . . ?
C5 N2 C2 C1 -176.5(3) . . . . ?
Co1 N2 C2 C1 2.9(3) . . . . ?
C5 N2 C2 C4 0.7(5) . . . . ?
Co1 N2 C2 C4 -179.8(2) . . . . ?
N1 C1 C2 N2 0.0(4) . . . . ?
C3 C1 C2 N2 177.7(3) . . . . ?
N1 C1 C2 C4 -177.4(3) . . . . ?
C3 C1 C2 C4 0.3(5) . . . . ?
C2 N2 C5 C6 -144.0(3) . . . . ?
Co1 N2 C5 C6 36.5(4) . . . . ?
N2 C5 C6 C7 -68.8(4) . . . . ?
C8 N3 C7 C6 145.8(3) . . . . ?
Co1 N3 C7 C6 -32.6(4) . . . . ?
C5 C6 C7 N3 66.2(4) . . . . ?
C7 N3 C8 C9 178.9(3) . . . . ?
Co1 N3 C8 C9 -2.5(3) . . . . ?
C7 N3 C8 C10 -0.1(5) . . . . ?
Co1 N3 C8 C10 178.5(3) . . . . ?
O2 N4 C9 C8 -179.9(2) . . . . ?
Co1 N4 C9 C8 4.5(3) . . . . ?
O2 N4 C9 C11 1.0(5) . . . . ?
Co1 N4 C9 C11 -174.6(3) . . . . ?
N3 C8 C9 N4 -1.2(4) . . . . ?
C10 C8 C9 N4 177.8(3) . . . . ?
N3 C8 C9 C11 177.9(3) . . . . ?
C10 C8 C9 C11 -3.1(5) . . . . ?
C16 N5 C12 C13 3.1(5) . . . . ?
Co1 N5 C12 C13 -174.1(3) . . . . ?
N5 C12 C13 C14 -1.0(6) . . . . ?
C12 C13 C14 C15 -2.0(6) . . . . ?
C12 C13 C14 C17 177.4(4) . . . . ?
C13 C14 C15 C16 2.8(6) . . . . ?
C17 C14 C15 C16 -176.7(4) . . . . ?
C12 N5 C16 C15 -2.3(5) . . . . ?
Co1 N5 C16 C15 174.9(3) . . . . ?
C14 C15 C16 N5 -0.7(6) . . . . ?
C13 C14 C17 C20 7.5(9) . . . . ?
C15 C14 C17 C20 -173.1(8) . . . . ?
C13 C14 C17 C18 -116.9(6) . . . . ?
C15 C14 C17 C18 62.4(7) . . . . ?
C13 C14 C17 C19 127.2(6) . . . . ?
C15 C14 C17 C19 -53.4(7) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O2 1.05(7) 1.58(7) 2.438(3) 136(6) .
O1 H1 N4 1.05(7) 2.34(8) 2.948(3) 115(5) .

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.37
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.061
# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 -0.010 252 38 ' '
2 0.042 0.688 0.444 7 0 ' '
3 0.074 0.696 0.271 7 0 ' '
4 0.194 0.431 0.206 10 0 ' '
5 0.186 0.464 0.024 5 0 ' '
6 0.306 0.069 0.706 10 0 ' '
7 0.313 0.036 0.524 4 0 ' '
8 0.500 0.500 0.219 252 38 ' '
9 0.431 0.806 0.794 9 0 ' '
10 0.464 0.814 0.976 5 0 ' '
11 0.542 0.187 0.944 7 0 ' '
12 0.574 0.196 0.771 7 0 ' '
13 0.694 0.931 0.706 10 0 ' '
14 0.686 0.964 0.524 5 0 ' '
15 0.806 0.569 0.206 10 0 ' '
16 0.813 0.536 0.024 4 0 ' '
17 0.931 0.306 0.294 9 0 ' '
18 0.964 0.314 0.476 5 0 ' '
_platon_squeeze_details          
;
Disordered solvent could not be modelled.
  
We anticipate that it is CH2Cl2, but there is no confirmation.
;


_contact_Crystallographer_name   'Richard Staples'
_contact_Crystallographer_email  staples@chemistry.msu.com
####################################################################### 
# 
# 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_final4
_database_code_depnum_ccdc_archive 'CCDC 1448834'
_audit_update_record             
;
2016-01-21 deposited with the CCDC.
2016-02-02 downloaded from the CCDC.
;
_audit_creation_date             2016-01-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C20 H30 Co N5 O2'
_chemical_formula_sum            'C20 H30 Co N5 O2'
_chemical_formula_weight         431.42
_chemical_melting_point          ?
_exptl_crystal_description       needle
_exptl_crystal_colour            'dark blue'
_diffrn_ambient_temperature      100.1
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   14.9757(13)
_cell_length_b                   10.6987(13)
_cell_length_c                   24.941(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.286(8)
_cell_angle_gamma                90
_cell_volume                     3954.3(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    812
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      17.06
_cell_measurement_theta_min      2.42
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.895
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5945
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0893 before and 0.0676 after correction.
The Ratio of minimum to maximum transmission is 0.7968.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1824
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.2264
_diffrn_reflns_av_unetI/netI     0.1783
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            24373
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.106
_diffrn_reflns_theta_max         24.106
_diffrn_reflns_theta_min         1.650
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1671
_reflns_number_total             3161
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.415
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.944
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3161
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1531
_refine_ls_R_factor_gt           0.0597
_refine_ls_restrained_S_all      0.944
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0220P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0700
_refine_ls_wR_factor_ref         0.0873
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C6(H6A,H6B), C8(H8A,H8B), C4(H4A,H4B), C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C16(H16), C13(H13), C15(H15)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C1(H1A,H1B,H1C), C18(H18A,H18B,H18C), C20(H20A,H20B,
 H20C), C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.51203(5) 0.35734(7) 0.42146(3) 0.0187(2) Uani 1 1 d . . . . .
O1 O 0.6718(2) 0.2083(3) 0.42794(14) 0.0266(9) Uani 1 1 d . . . . .
N1 N 0.4450(2) 0.2593(4) 0.36038(15) 0.0160(10) Uani 1 1 d . . . . .
O2 O 0.6618(2) 0.3841(3) 0.36426(13) 0.0276(10) Uani 1 1 d . . . . .
N2 N 0.4561(3) 0.3017(4) 0.48099(15) 0.0181(11) Uani 1 1 d . . . . .
N5 N 0.4534(3) 0.5142(4) 0.41506(15) 0.0180(11) Uani 1 1 d . . . . .
N4 N 0.5900(3) 0.4393(4) 0.38212(16) 0.0212(11) Uani 1 1 d . . . . .
N3 N 0.5975(3) 0.2394(4) 0.45028(16) 0.0193(11) Uani 1 1 d . . . . .
C3 C 0.5032(3) 0.2185(5) 0.5127(2) 0.0207(13) Uani 1 1 d . . . . .
C12 C 0.4141(3) 0.1448(5) 0.36912(19) 0.0212(12) Uani 1 1 d . . . . .
H12 H 0.4197 0.1158 0.4055 0.025 Uiso 1 1 calc R . . . .
C14 C 0.3644(3) 0.1044(4) 0.2747(2) 0.0186(14) Uani 1 1 d . . . . .
C2 C 0.5837(3) 0.1793(5) 0.4947(2) 0.0228(14) Uani 1 1 d . . . . .
C16 C 0.4334(3) 0.2974(5) 0.3091(2) 0.0209(13) Uani 1 1 d . . . . .
H16 H 0.4529 0.3793 0.3016 0.025 Uiso 1 1 calc R . . . .
C9 C 0.4937(4) 0.6006(5) 0.3891(2) 0.0227(14) Uani 1 1 d . . . . .
C13 C 0.3747(3) 0.0663(5) 0.3287(2) 0.0222(14) Uani 1 1 d . . . . .
H13 H 0.3545 -0.0142 0.3376 0.027 Uiso 1 1 calc R . . . .
C7 C 0.3718(3) 0.5407(5) 0.4390(2) 0.0208(14) Uani 1 1 d . . . . .
H7A H 0.3329 0.5991 0.4152 0.025 Uiso 1 1 calc R . . . .
H7B H 0.3886 0.5815 0.4746 0.025 Uiso 1 1 calc R . . . .
C6 C 0.3203(3) 0.4224(5) 0.44603(19) 0.0217(14) Uani 1 1 d . . . . .
H6A H 0.3141 0.3736 0.4120 0.026 Uiso 1 1 calc R . . . .
H6B H 0.2590 0.4440 0.4534 0.026 Uiso 1 1 calc R . . . .
C15 C 0.3949(3) 0.2256(5) 0.2661(2) 0.0204(13) Uani 1 1 d . . . . .
H15 H 0.3890 0.2583 0.2303 0.024 Uiso 1 1 calc R . . . .
C8 C 0.4655(3) 0.7374(5) 0.3853(2) 0.0299(15) Uani 1 1 d . . . . .
H8A H 0.4001 0.7436 0.3872 0.036 Uiso 1 1 calc R . . . .
H8B H 0.4763 0.7713 0.3499 0.036 Uiso 1 1 calc R . . . .
C10 C 0.5713(4) 0.5566(6) 0.3676(2) 0.0237(14) Uani 1 1 d . . . . .
C17 C 0.3231(3) 0.0227(5) 0.2272(2) 0.0221(14) Uani 1 1 d . . . . .
C4 C 0.4804(4) 0.1808(5) 0.56748(19) 0.0288(15) Uani 1 1 d . . . . .
H4A H 0.4954 0.0914 0.5740 0.035 Uiso 1 1 calc R . . . .
H4B H 0.4148 0.1912 0.5678 0.035 Uiso 1 1 calc R . . . .
C19 C 0.2364(3) 0.0861(5) 0.19930(19) 0.0307(15) Uani 1 1 d . . . . .
H19A H 0.1943 0.0974 0.2256 0.046 Uiso 1 1 calc GR . . . .
H19B H 0.2082 0.0335 0.1694 0.046 Uiso 1 1 calc GR . . . .
H19C H 0.2513 0.1677 0.1852 0.046 Uiso 1 1 calc GR . . . .
C1 C 0.6509(4) 0.0874(5) 0.5223(2) 0.0325(16) Uani 1 1 d . . . . .
H1A H 0.6365 0.0035 0.5078 0.049 Uiso 1 1 calc GR . . . .
H1B H 0.6484 0.0878 0.5613 0.049 Uiso 1 1 calc GR . . . .
H1C H 0.7117 0.1108 0.5158 0.049 Uiso 1 1 calc GR . . . .
C18 C 0.3013(3) -0.1069(5) 0.2468(2) 0.0323(16) Uani 1 1 d . . . . .
H18A H 0.3569 -0.1469 0.2642 0.048 Uiso 1 1 calc GR . . . .
H18B H 0.2745 -0.1575 0.2158 0.048 Uiso 1 1 calc GR . . . .
H18C H 0.2586 -0.0998 0.2729 0.048 Uiso 1 1 calc GR . . . .
C5 C 0.3672(3) 0.3424(5) 0.49224(19) 0.0260(14) Uani 1 1 d . . . . .
H5A H 0.3742 0.3912 0.5263 0.031 Uiso 1 1 calc R . . . .
H5B H 0.3296 0.2683 0.4971 0.031 Uiso 1 1 calc R . . . .
C20 C 0.3898(3) 0.0119(5) 0.1862(2) 0.0303(15) Uani 1 1 d . . . . .
H20A H 0.4064 0.0956 0.1752 0.045 Uiso 1 1 calc GR . . . .
H20B H 0.3617 -0.0347 0.1543 0.045 Uiso 1 1 calc GR . . . .
H20C H 0.4441 -0.0323 0.2029 0.045 Uiso 1 1 calc GR . . . .
C11 C 0.6290(3) 0.6301(6) 0.3358(2) 0.0437(17) Uani 1 1 d . . . . .
H11A H 0.6744 0.6757 0.3606 0.066 Uiso 1 1 calc GR . . . .
H11B H 0.5917 0.6897 0.3126 0.066 Uiso 1 1 calc GR . . . .
H11C H 0.6592 0.5736 0.3133 0.066 Uiso 1 1 calc GR . . . .
H1 H 0.671(3) 0.278(5) 0.3963(18) 0.030(15) Uiso 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 1.997(4) . ?
Co1 N2 1.902(4) . ?
Co1 N5 1.890(4) . ?
Co1 N4 1.850(4) . ?
Co1 N3 1.866(4) . ?
O1 N3 1.356(4) . ?
O1 H1 1.09(5) . ?
N1 C12 1.339(6) . ?
N1 C16 1.330(5) . ?
O2 N4 1.357(5) . ?
O2 H1 1.38(5) . ?
N2 C3 1.324(6) . ?
N2 C5 1.466(5) . ?
N5 C9 1.324(6) . ?
N5 C7 1.462(6) . ?
N4 C10 1.326(6) . ?
N3 C2 1.322(6) . ?
C3 C2 1.410(7) . ?
C3 C4 1.511(6) . ?
C12 H12 0.9500 . ?
C12 C13 1.379(6) . ?
C14 C13 1.394(6) . ?
C14 C15 1.401(6) . ?
C14 C17 1.531(6) . ?
C2 C1 1.501(7) . ?
C16 H16 0.9500 . ?
C16 C15 1.376(6) . ?
C9 C8 1.522(7) . ?
C9 C10 1.429(7) . ?
C13 H13 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C6 1.506(6) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C5 1.523(6) . ?
C15 H15 0.9500 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C4 1.591(6) 5_666 ?
C10 C11 1.480(7) . ?
C17 C19 1.539(6) . ?
C17 C18 1.521(6) . ?
C17 C20 1.534(7) . ?
C4 C8 1.592(6) 5_666 ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Co1 N1 101.66(16) . . ?
N5 Co1 N1 103.04(16) . . ?
N5 Co1 N2 95.28(18) . . ?
N4 Co1 N1 97.48(17) . . ?
N4 Co1 N2 160.81(16) . . ?
N4 Co1 N5 81.71(19) . . ?
N4 Co1 N3 94.26(19) . . ?
N3 Co1 N1 100.38(17) . . ?
N3 Co1 N2 80.95(18) . . ?
N3 Co1 N5 156.56(16) . . ?
N3 O1 H1 102(2) . . ?
C12 N1 Co1 120.3(3) . . ?
C16 N1 Co1 123.7(4) . . ?
C16 N1 C12 115.9(4) . . ?
N4 O2 H1 100.6(18) . . ?
C3 N2 Co1 114.8(3) . . ?
C3 N2 C5 120.3(4) . . ?
C5 N2 Co1 124.8(3) . . ?
C9 N5 Co1 115.0(4) . . ?
C9 N5 C7 122.0(4) . . ?
C7 N5 Co1 122.9(3) . . ?
O2 N4 Co1 123.9(3) . . ?
C10 N4 Co1 118.0(4) . . ?
C10 N4 O2 117.9(4) . . ?
O1 N3 Co1 124.5(3) . . ?
C2 N3 Co1 118.0(3) . . ?
C2 N3 O1 117.5(4) . . ?
N2 C3 C2 114.6(5) . . ?
N2 C3 C4 123.4(5) . . ?
C2 C3 C4 121.5(5) . . ?
N1 C12 H12 118.0 . . ?
N1 C12 C13 124.1(5) . . ?
C13 C12 H12 118.0 . . ?
C13 C14 C15 115.2(5) . . ?
C13 C14 C17 123.8(5) . . ?
C15 C14 C17 120.9(5) . . ?
N3 C2 C3 111.5(5) . . ?
N3 C2 C1 121.8(5) . . ?
C3 C2 C1 126.6(5) . . ?
N1 C16 H16 118.0 . . ?
N1 C16 C15 124.1(5) . . ?
C15 C16 H16 118.0 . . ?
N5 C9 C8 124.1(5) . . ?
N5 C9 C10 114.0(5) . . ?
C10 C9 C8 121.8(5) . . ?
C12 C13 C14 120.3(5) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
N5 C7 H7A 109.5 . . ?
N5 C7 H7B 109.5 . . ?
N5 C7 C6 110.9(4) . . ?
H7A C7 H7B 108.1 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C7 C6 H6A 109.2 . . ?
C7 C6 H6B 109.2 . . ?
C7 C6 C5 111.9(4) . . ?
H6A C6 H6B 107.9 . . ?
C5 C6 H6A 109.2 . . ?
C5 C6 H6B 109.2 . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.4(5) . . ?
C16 C15 H15 119.8 . . ?
C9 C8 H8A 109.2 . . ?
C9 C8 H8B 109.2 . . ?
C9 C8 C4 112.1(4) . 5_666 ?
H8A C8 H8B 107.9 . . ?
C4 C8 H8A 109.2 5_666 . ?
C4 C8 H8B 109.2 5_666 . ?
N4 C10 C9 111.1(5) . . ?
N4 C10 C11 122.2(5) . . ?
C9 C10 C11 126.6(5) . . ?
C14 C17 C19 108.6(4) . . ?
C14 C17 C20 109.2(4) . . ?
C18 C17 C14 110.7(4) . . ?
C18 C17 C19 109.9(4) . . ?
C18 C17 C20 109.6(4) . . ?
C20 C17 C19 108.7(4) . . ?
C3 C4 C8 111.4(4) . 5_666 ?
C3 C4 H4A 109.3 . . ?
C3 C4 H4B 109.3 . . ?
C8 C4 H4A 109.3 5_666 . ?
C8 C4 H4B 109.3 5_666 . ?
H4A C4 H4B 108.0 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N2 C5 C6 110.7(4) . . ?
N2 C5 H5A 109.5 . . ?
N2 C5 H5B 109.5 . . ?
C6 C5 H5A 109.5 . . ?
C6 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_symmetry_cell_setting           ?
_symmetry_space_group_name_h-m   ?
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?

_chemical_properties_physical    
'Air-sensitive, Moisture-sensitive, Oxygen-sensitive'
####################################################################### 
# 
# 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_cnv712_0m
_database_code_depnum_ccdc_archive 'CCDC 1449138'
_audit_update_record             
;
2016-01-21 deposited with the CCDC.
2016-02-02 downloaded from the CCDC.
;
_audit_creation_date             2014-08-28
_audit_creation_method           
;
  Olex2 1.2
  (compiled Apr  9 2013 14:10:59, GUI svn.r4458)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C29 H45 Co N6 O2, 2(F6 P), C H4 O'
_chemical_formula_sum            'C30 H49 Co F12 N6 O3 P2'
_chemical_formula_weight         890.62
_chemical_absolute_configuration ?
_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'
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_symmetry_int_tables_number      14
_cell_length_a                   12.5242(14)
_cell_length_b                   16.7919(19)
_cell_length_c                   18.462(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.4660(10)
_cell_angle_gamma                90.00
_cell_volume                     3881.4(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9976
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.31
_cell_measurement_theta_min      2.29
_exptl_absorpt_coefficient_mu    0.622
_exptl_absorpt_correction_T_max  0.9135
_exptl_absorpt_correction_T_min  0.8445
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       chunk
_exptl_crystal_F_000             1840
_exptl_crystal_size_max          0.281
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.148
_exptl_special_details           
;
Data was collected using a BRUKER CCD (charge coupled device) based
diffractometer equipped with an Oxford low-temperature apparatus operating at
173 K.  A suitable crystal was chosen and mounted on a glass fiber or nylon loop
using Paratone oil for Mo radiation and Mineral oil for Copper radiation.  Data 
were measured using omega and phi scans of 0.5° per frame 
for 30 s. The total number of images were based on 
results from the program COSMO where redundancy was expected to be 4 and 
completeness to 0.83Å to 100%. Cell parameters were
retrieved using APEX II software and refined using SAINT on all observed
reflections.Data reduction was performed using the SAINT software which 
corrects for Lp. Scaling and absorption corrections were applied using SADABS6 
multi-scan technique, supplied by George Sheldrick.  The structures are solved 
by the direct method using the SHELXS-97 program and refined by least squares 
method on F2, SHELXL-97, incorporated in SHELXTL-PC V 6.14. 
 
All H atoms were placed in calculated positions and refined using a riding
model except for that of the hydrogen between atoms O1 and O2, which was 
found and refined isotropically.
C-H(aromatic) = 0.94  Å and Uiso(H) = 1.2Ueq(C)
C-H (alaphatic) = 0.99 Å and Uiso(H) = 1.2Ueq(C)
CH2 = 0.98 Å and Uiso(H) = 1.2Ueq(C)
CH3 = 0.97Å and Uiso(H) = 1.5Ueq(C)
N-H = 0.86 (0.92)Å and Uiso(H) = 1.2 Ueq(N)
O-H(alcohol) = 0.85Åand Uiso(H) = 1.2Ueq(O)
O-H(acid) = 0.82Å and Uiso(H) = 1.5Ueq(O)
;
_diffrn_reflns_av_R_equivalents  0.0504
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            31374
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         1.64
_diffrn_ambient_temperature      173.15
_diffrn_detector_area_resol_mean 836.6
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω,and/f 0.5 deg'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_reflns_number_gt                5184
_reflns_number_total             7102
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'APEX2 (BRUKER, V2010.11-3, 2010)'
_computing_data_collection       'COSMO (BRUKER, V1.61, 2009)'
_computing_data_reduction        'SAINT (BRUKER, V7.68A, 2010)'
_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 (Sheldrick, Acta Cryst. A64 2008, 112-122)'
_computing_structure_solution    
'SHELXS (Sheldrick, Acta Cryst. A64 2008, 112-122)'
_refine_diff_density_max         0.749
_refine_diff_density_min         -0.500
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     503
_refine_ls_number_reflns         7102
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0827
_refine_ls_R_factor_gt           0.0579
_refine_ls_restrained_S_all      1.054
_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)+(0.0863P)²+4.6491P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1515
_refine_ls_wR_factor_ref         0.1704
_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
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C15(H15), C16(H16), C21(H21), C22(H22), C24(H24), C25(H25)
2.c Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C4(H4A,H4B,H4C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C),
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C27(H27A,H27B,
 H27C), C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C1S(H1S1,H1S2,H1S3)
2.d Idealised tetrahedral OH refined as rotating group:
 O1S(H1S)
;
_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_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Co1 Co 0.45354(4) 0.79253(3) 0.04972(3) 0.02617(16) Uani 1 1 d . . .
O1 O 0.3901(2) 0.95301(16) 0.03574(19) 0.0498(8) Uani 1 1 d . . .
O2 O 0.3387(3) 0.8659(2) -0.06700(18) 0.0551(9) Uani 1 1 d . . .
H1 H 0.360(5) 0.914(3) -0.029(3) 0.081(18) Uiso 1 1 d . . .
N1 N 0.3774(3) 0.7986(2) -0.04051(18) 0.0376(8) Uani 1 1 d . . .
N2 N 0.4693(2) 0.68423(18) 0.01934(17) 0.0326(7) Uani 1 1 d . . .
N3 N 0.5201(2) 0.78511(18) 0.14383(16) 0.0307(7) Uani 1 1 d . . .
N4 N 0.4322(2) 0.89864(18) 0.07962(19) 0.0352(7) Uani 1 1 d . . .
N5 N 0.5885(2) 0.82338(17) 0.00462(15) 0.0271(6) Uani 1 1 d . . .
N6 N 0.3153(2) 0.76551(17) 0.09280(16) 0.0283(7) Uani 1 1 d . . .
C1 C 0.3567(3) 0.7316(3) -0.0723(2) 0.0414(10) Uani 1 1 d . . .
C2 C 0.4128(3) 0.6649(2) -0.0368(2) 0.0386(9) Uani 1 1 d . . .
C3 C 0.2839(4) 0.7255(4) -0.1375(3) 0.0722(17) Uani 1 1 d . . .
H3A H 0.2134 0.7071 -0.1228 0.108 Uiso 1 1 calc . . GR
H3B H 0.3136 0.6876 -0.1720 0.108 Uiso 1 1 calc . . GR
H3C H 0.2769 0.7779 -0.1605 0.108 Uiso 1 1 calc . . GR
C4 C 0.4045(4) 0.5833(3) -0.0674(3) 0.0603(14) Uani 1 1 d . . .
H4A H 0.4711 0.5698 -0.0913 0.091 Uiso 1 1 calc . . GR
H4B H 0.3450 0.5811 -0.1028 0.091 Uiso 1 1 calc . . GR
H4C H 0.3920 0.5451 -0.0284 0.091 Uiso 1 1 calc . . GR
C5 C 0.5383(3) 0.6259(2) 0.0583(2) 0.0424(10) Uani 1 1 d . . .
H5A H 0.5747 0.5922 0.0225 0.051 Uiso 1 1 calc . . R
H5B H 0.4932 0.5908 0.0879 0.051 Uiso 1 1 calc . . R
C6 C 0.6215(3) 0.6661(3) 0.1071(2) 0.0434(10) Uani 1 1 d . . .
H6A H 0.6646 0.7022 0.0772 0.052 Uiso 1 1 calc . . R
H6B H 0.6701 0.6247 0.1272 0.052 Uiso 1 1 calc . . R
C7 C 0.5770(3) 0.7135(3) 0.1697(2) 0.0424(10) Uani 1 1 d . . .
H7A H 0.5274 0.6796 0.1969 0.051 Uiso 1 1 calc . . R
H7B H 0.6363 0.7294 0.2031 0.051 Uiso 1 1 calc . . R
C8 C 0.5056(3) 0.8469(3) 0.1840(2) 0.0379(9) Uani 1 1 d . . .
C9 C 0.4555(3) 0.9148(2) 0.1464(2) 0.0411(10) Uani 1 1 d . . .
C10 C 0.5374(4) 0.8536(3) 0.2618(2) 0.0590(13) Uani 1 1 d . . .
H10A H 0.5607 0.8014 0.2800 0.089 Uiso 1 1 calc . . GR
H10B H 0.4763 0.8720 0.2894 0.089 Uiso 1 1 calc . . GR
H10C H 0.5962 0.8918 0.2674 0.089 Uiso 1 1 calc . . GR
C11 C 0.4367(4) 0.9947(3) 0.1789(3) 0.0651(15) Uani 1 1 d . . .
H11A H 0.4372 1.0353 0.1407 0.098 Uiso 1 1 calc . . GR
H11B H 0.4932 1.0062 0.2150 0.098 Uiso 1 1 calc . . GR
H11C H 0.3672 0.9951 0.2022 0.098 Uiso 1 1 calc . . GR
C12 C 0.6160(3) 0.7937(2) -0.0596(2) 0.0346(9) Uani 1 1 d . . .
H12 H 0.5687 0.7575 -0.0835 0.042 Uiso 1 1 calc . . R
C13 C 0.7092(3) 0.8132(2) -0.0921(2) 0.0374(9) Uani 1 1 d . . .
H13 H 0.7251 0.7899 -0.1375 0.045 Uiso 1 1 calc . . R
C14 C 0.7811(3) 0.8663(2) -0.0604(2) 0.0315(8) Uani 1 1 d . . .
C15 C 0.7527(3) 0.8960(2) 0.0063(2) 0.0313(8) Uani 1 1 d . . .
H15 H 0.7992 0.9320 0.0313 0.038 Uiso 1 1 calc . . R
C16 C 0.6580(3) 0.8741(2) 0.0370(2) 0.0301(8) Uani 1 1 d . . .
H16 H 0.6411 0.8956 0.0829 0.036 Uiso 1 1 calc . . R
C17 C 0.8849(3) 0.8918(2) -0.0955(2) 0.0384(9) Uani 1 1 d . . .
C18 C 0.8866(4) 0.9836(3) -0.1015(3) 0.0642(14) Uani 1 1 d . . .
H18A H 0.8801 1.0070 -0.0532 0.096 Uiso 1 1 calc . . GR
H18B H 0.8267 1.0013 -0.1327 0.096 Uiso 1 1 calc . . GR
H18C H 0.9540 1.0006 -0.1225 0.096 Uiso 1 1 calc . . GR
C19 C 0.8938(5) 0.8610(4) -0.1718(3) 0.0791(18) Uani 1 1 d . . .
H19A H 0.9606 0.8800 -0.1923 0.119 Uiso 1 1 calc . . GR
H19B H 0.8331 0.8803 -0.2014 0.119 Uiso 1 1 calc . . GR
H19C H 0.8934 0.8026 -0.1713 0.119 Uiso 1 1 calc . . GR
C20 C 0.9777(4) 0.8655(4) -0.0481(4) 0.0809(19) Uani 1 1 d . . .
H20A H 0.9772 0.8073 -0.0439 0.121 Uiso 1 1 calc . . GR
H20B H 0.9718 0.8893 0.0001 0.121 Uiso 1 1 calc . . GR
H20C H 1.0446 0.8827 -0.0696 0.121 Uiso 1 1 calc . . GR
C21 C 0.2977(3) 0.6978(2) 0.1285(2) 0.0349(9) Uani 1 1 d . . .
H21 H 0.3559 0.6620 0.1357 0.042 Uiso 1 1 calc . . R
C22 C 0.2004(3) 0.6769(2) 0.1552(2) 0.0385(9) Uani 1 1 d . . .
H22 H 0.1930 0.6278 0.1801 0.046 Uiso 1 1 calc . . R
C23 C 0.1128(3) 0.7267(2) 0.1464(2) 0.0329(8) Uani 1 1 d . . .
C24 C 0.1317(3) 0.7972(2) 0.1110(2) 0.0407(10) Uani 1 1 d . . .
H24 H 0.0753 0.8346 0.1046 0.049 Uiso 1 1 calc . . R
C25 C 0.2307(3) 0.8146(2) 0.0846(2) 0.0411(10) Uani 1 1 d . . .
H25 H 0.2398 0.8633 0.0594 0.049 Uiso 1 1 calc . . R
C26 C 0.0037(3) 0.7033(2) 0.1746(2) 0.0409(10) Uani 1 1 d . . .
C27 C -0.0282(4) 0.6222(3) 0.1425(3) 0.0627(14) Uani 1 1 d . . .
H27A H -0.0342 0.6265 0.0896 0.094 Uiso 1 1 calc . . GR
H27B H -0.0971 0.6058 0.1616 0.094 Uiso 1 1 calc . . GR
H27C H 0.0263 0.5826 0.1557 0.094 Uiso 1 1 calc . . GR
C28 C -0.0825(4) 0.7633(3) 0.1549(3) 0.0634(14) Uani 1 1 d . . .
H28A H -0.0628 0.8154 0.1749 0.095 Uiso 1 1 calc . . GR
H28B H -0.1504 0.7460 0.1749 0.095 Uiso 1 1 calc . . GR
H28C H -0.0899 0.7672 0.1020 0.095 Uiso 1 1 calc . . GR
C29 C 0.0129(4) 0.6964(3) 0.2566(3) 0.0585(13) Uani 1 1 d . . .
H29A H 0.0698 0.6587 0.2698 0.088 Uiso 1 1 calc . . GR
H29B H -0.0550 0.6774 0.2754 0.088 Uiso 1 1 calc . . GR
H29C H 0.0298 0.7487 0.2775 0.088 Uiso 1 1 calc . . GR
P1 P 0.29542(9) 0.49611(7) 0.72136(6) 0.0426(3) Uani 1 1 d . . .
F1 F 0.2384(3) 0.4998(2) 0.79713(17) 0.0806(10) Uani 1 1 d . . .
F2 F 0.3505(3) 0.4948(3) 0.64678(19) 0.1196(17) Uani 1 1 d . . .
F3 F 0.2923(4) 0.4031(2) 0.7227(2) 0.1165(16) Uani 1 1 d . . .
F4 F 0.4054(3) 0.4920(3) 0.7639(2) 0.1135(15) Uani 1 1 d . . .
F5 F 0.1836(3) 0.4970(2) 0.6800(2) 0.0891(11) Uani 1 1 d . . .
F6 F 0.2915(4) 0.5890(2) 0.7214(3) 0.1226(16) Uani 1 1 d . . .
P2 P 0.73269(12) 0.57277(8) 0.86296(10) 0.0731(5) Uani 1 1 d . . .
F7 F 0.8399(3) 0.5255(2) 0.8717(3) 0.1269(17) Uani 1 1 d . . .
F8 F 0.7487(6) 0.6148(4) 0.9365(4) 0.189(3) Uani 1 1 d . . .
F9 F 0.6280(3) 0.6232(2) 0.8567(3) 0.1282(18) Uani 1 1 d . . .
F10 F 0.6706(4) 0.5045(3) 0.8993(4) 0.176(3) Uani 1 1 d . . .
F11 F 0.7151(6) 0.5296(4) 0.7922(4) 0.194(3) Uani 1 1 d . . .
F12 F 0.7924(4) 0.6413(3) 0.8275(4) 0.182(3) Uani 1 1 d . . .
O1S O 0.0786(10) 0.5922(12) 0.9510(5) 0.375(11) Uani 1 1 d . . .
H1S H 0.0953 0.5626 0.9165 0.563 Uiso 1 1 calc . . GR
C1S C 0.1693(6) 0.6097(4) 0.9931(3) 0.090(2) Uani 1 1 d . . .
H1S1 H 0.2312 0.5824 0.9731 0.136 Uiso 1 1 calc . . GR
H1S2 H 0.1590 0.5918 1.0429 0.136 Uiso 1 1 calc . . GR
H1S3 H 0.1818 0.6674 0.9928 0.136 Uiso 1 1 calc . . GR


_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 1.901(3) . ?
Co1 N2 1.915(3) . ?
Co1 N3 1.912(3) . ?
Co1 N4 1.886(3) . ?
Co1 N5 1.973(3) . ?
Co1 N6 1.977(3) . ?
O1 H1 1.41(6) . ?
O1 N4 1.321(4) . ?
O2 H1 1.09(6) . ?
O2 N1 1.319(4) . ?
N1 C1 1.291(5) . ?
N2 C2 1.282(5) . ?
N2 C5 1.480(5) . ?
N3 C7 1.470(5) . ?
N3 C8 1.292(5) . ?
N4 C9 1.288(5) . ?
N5 C12 1.339(5) . ?
N5 C16 1.347(4) . ?
N6 C21 1.335(5) . ?
N6 C25 1.347(5) . ?
C1 C2 1.468(6) . ?
C1 C3 1.496(6) . ?
C2 C4 1.485(6) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.519(6) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.521(6) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.467(6) . ?
C8 C10 1.485(6) . ?
C9 C11 1.491(6) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12 0.9500 . ?
C12 C13 1.366(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.387(5) . ?
C14 C15 1.384(5) . ?
C14 C17 1.529(5) . ?
C15 H15 0.9500 . ?
C15 C16 1.378(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.545(6) . ?
C17 C19 1.507(6) . ?
C17 C20 1.503(7) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21 0.9500 . ?
C21 C22 1.372(5) . ?
C22 H22 0.9500 . ?
C22 C23 1.386(5) . ?
C23 C24 1.376(5) . ?
C23 C26 1.526(5) . ?
C24 H24 0.9500 . ?
C24 C25 1.374(6) . ?
C25 H25 0.9500 . ?
C26 C27 1.534(6) . ?
C26 C28 1.514(6) . ?
C26 C29 1.519(6) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
P1 F1 1.588(3) . ?
P1 F2 1.556(3) . ?
P1 F3 1.563(4) . ?
P1 F4 1.569(3) . ?
P1 F5 1.578(3) . ?
P1 F6 1.561(4) . ?
P2 F7 1.564(4) . ?
P2 F8 1.539(6) . ?
P2 F9 1.563(4) . ?
P2 F10 1.547(4) . ?
P2 F11 1.505(6) . ?
P2 F12 1.528(4) . ?
O1S H1S 0.8400 . ?
O1S C1S 1.391(10) . ?
C1S H1S1 0.9800 . ?
C1S H1S2 0.9800 . ?
C1S H1S3 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Co1 N2 81.21(14) . . ?
N1 Co1 N3 175.70(13) . . ?
N1 Co1 N5 91.86(13) . . ?
N1 Co1 N6 86.54(13) . . ?
N2 Co1 N5 91.71(13) . . ?
N2 Co1 N6 89.88(13) . . ?
N3 Co1 N2 99.12(14) . . ?
N3 Co1 N5 92.42(12) . . ?
N3 Co1 N6 89.17(12) . . ?
N4 Co1 N1 97.71(15) . . ?
N4 Co1 N2 177.76(13) . . ?
N4 Co1 N3 81.81(14) . . ?
N4 Co1 N5 90.29(13) . . ?
N4 Co1 N6 88.09(13) . . ?
N5 Co1 N6 177.55(12) . . ?
N4 O1 H1 107(2) . . ?
N1 O2 H1 108(3) . . ?
O2 N1 Co1 122.8(3) . . ?
C1 N1 Co1 116.2(3) . . ?
C1 N1 O2 120.7(4) . . ?
C2 N2 Co1 114.7(3) . . ?
C2 N2 C5 121.9(3) . . ?
C5 N2 Co1 123.4(3) . . ?
C7 N3 Co1 123.0(3) . . ?
C8 N3 Co1 113.9(3) . . ?
C8 N3 C7 123.0(3) . . ?
O1 N4 Co1 122.1(3) . . ?
C9 N4 Co1 116.6(3) . . ?
C9 N4 O1 121.2(3) . . ?
C12 N5 Co1 121.2(2) . . ?
C12 N5 C16 116.8(3) . . ?
C16 N5 Co1 122.0(2) . . ?
C21 N6 Co1 123.4(2) . . ?
C21 N6 C25 116.0(3) . . ?
C25 N6 Co1 120.6(2) . . ?
N1 C1 C2 111.9(3) . . ?
N1 C1 C3 122.4(4) . . ?
C2 C1 C3 125.6(4) . . ?
N2 C2 C1 114.5(3) . . ?
N2 C2 C4 125.0(4) . . ?
C1 C2 C4 120.4(4) . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N2 C5 H5A 109.2 . . ?
N2 C5 H5B 109.2 . . ?
N2 C5 C6 112.2(3) . . ?
H5A C5 H5B 107.9 . . ?
C6 C5 H5A 109.2 . . ?
C6 C5 H5B 109.2 . . ?
C5 C6 H6A 108.5 . . ?
C5 C6 H6B 108.5 . . ?
C5 C6 C7 115.1(3) . . ?
H6A C6 H6B 107.5 . . ?
C7 C6 H6A 108.5 . . ?
C7 C6 H6B 108.5 . . ?
N3 C7 C6 111.5(3) . . ?
N3 C7 H7A 109.3 . . ?
N3 C7 H7B 109.3 . . ?
C6 C7 H7A 109.3 . . ?
C6 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
N3 C8 C9 114.6(3) . . ?
N3 C8 C10 125.3(4) . . ?
C9 C8 C10 120.1(4) . . ?
N4 C9 C8 111.9(3) . . ?
N4 C9 C11 122.7(4) . . ?
C8 C9 C11 125.3(4) . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N5 C12 H12 118.6 . . ?
N5 C12 C13 122.9(4) . . ?
C13 C12 H12 118.6 . . ?
C12 C13 H13 119.3 . . ?
C12 C13 C14 121.4(4) . . ?
C14 C13 H13 119.3 . . ?
C13 C14 C17 123.4(3) . . ?
C15 C14 C13 115.4(3) . . ?
C15 C14 C17 121.2(3) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 C14 120.9(3) . . ?
C16 C15 H15 119.5 . . ?
N5 C16 C15 122.6(3) . . ?
N5 C16 H16 118.7 . . ?
C15 C16 H16 118.7 . . ?
C14 C17 C18 108.8(3) . . ?
C19 C17 C14 112.6(3) . . ?
C19 C17 C18 105.9(4) . . ?
C20 C17 C14 108.9(4) . . ?
C20 C17 C18 108.9(4) . . ?
C20 C17 C19 111.7(5) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N6 C21 H21 118.2 . . ?
N6 C21 C22 123.6(3) . . ?
C22 C21 H21 118.2 . . ?
C21 C22 H22 119.6 . . ?
C21 C22 C23 120.8(4) . . ?
C23 C22 H22 119.6 . . ?
C22 C23 C26 121.2(3) . . ?
C24 C23 C22 115.4(3) . . ?
C24 C23 C26 123.4(3) . . ?
C23 C24 H24 119.4 . . ?
C25 C24 C23 121.3(4) . . ?
C25 C24 H24 119.4 . . ?
N6 C25 C24 122.9(4) . . ?
N6 C25 H25 118.5 . . ?
C24 C25 H25 118.5 . . ?
C23 C26 C27 108.9(3) . . ?
C28 C26 C23 112.7(3) . . ?
C28 C26 C27 108.7(4) . . ?
C28 C26 C29 109.0(4) . . ?
C29 C26 C23 108.3(4) . . ?
C29 C26 C27 109.3(4) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C26 C28 H28A 109.5 . . ?
C26 C28 H28B 109.5 . . ?
C26 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C26 C29 H29A 109.5 . . ?
C26 C29 H29B 109.5 . . ?
C26 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
F2 P1 F1 178.5(2) . . ?
F2 P1 F3 90.7(3) . . ?
F2 P1 F4 92.2(2) . . ?
F2 P1 F5 88.9(2) . . ?
F2 P1 F6 91.7(2) . . ?
F3 P1 F1 90.7(2) . . ?
F3 P1 F4 88.3(3) . . ?
F3 P1 F5 89.7(2) . . ?
F4 P1 F1 88.3(2) . . ?
F4 P1 F5 177.8(3) . . ?
F5 P1 F1 90.7(2) . . ?
F6 P1 F1 86.9(2) . . ?
F6 P1 F3 176.6(3) . . ?
F6 P1 F4 94.1(3) . . ?
F6 P1 F5 87.9(2) . . ?
F8 P2 F7 92.9(3) . . ?
F8 P2 F9 84.7(3) . . ?
F8 P2 F10 90.7(4) . . ?
F9 P2 F7 177.2(3) . . ?
F10 P2 F7 91.1(3) . . ?
F10 P2 F9 90.2(2) . . ?
F11 P2 F7 87.2(3) . . ?
F11 P2 F8 178.1(5) . . ?
F11 P2 F9 95.4(3) . . ?
F11 P2 F10 87.4(4) . . ?
F11 P2 F12 93.1(4) . . ?
F12 P2 F7 89.9(3) . . ?
F12 P2 F8 88.8(4) . . ?
F12 P2 F9 88.8(3) . . ?
F12 P2 F10 178.9(3) . . ?
C1S O1S H1S 109.5 . . ?
O1S C1S H1S1 109.5 . . ?
O1S C1S H1S2 109.5 . . ?
O1S C1S H1S3 109.5 . . ?
H1S1 C1S H1S2 109.5 . . ?
H1S1 C1S H1S3 109.5 . . ?
H1S2 C1S H1S3 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H1 O1 1.09(6) 1.41(6) 2.467(5) 161(5) .

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Co1 N1 C1 C2 -9.5(4) . . . . ?
Co1 N1 C1 C3 170.7(3) . . . . ?
Co1 N2 C2 C1 7.1(4) . . . . ?
Co1 N2 C2 C4 -175.0(3) . . . . ?
Co1 N2 C5 C6 -19.6(4) . . . . ?
Co1 N3 C7 C6 27.0(5) . . . . ?
Co1 N3 C8 C9 -8.7(4) . . . . ?
Co1 N3 C8 C10 172.6(3) . . . . ?
Co1 N4 C9 C8 6.1(4) . . . . ?
Co1 N4 C9 C11 -176.3(3) . . . . ?
Co1 N5 C12 C13 -179.5(3) . . . . ?
Co1 N5 C16 C15 179.8(3) . . . . ?
Co1 N6 C21 C22 -176.5(3) . . . . ?
Co1 N6 C25 C24 177.4(3) . . . . ?
O1 N4 C9 C8 -177.4(3) . . . . ?
O1 N4 C9 C11 0.2(6) . . . . ?
O2 N1 C1 C2 176.4(3) . . . . ?
O2 N1 C1 C3 -3.5(6) . . . . ?
N1 Co1 N2 C2 -9.5(3) . . . . ?
N1 Co1 N2 C5 172.4(3) . . . . ?
N1 Co1 N3 C7 101.9(19) . . . . ?
N1 Co1 N3 C8 -74.5(19) . . . . ?
N1 Co1 N4 O1 -9.4(3) . . . . ?
N1 Co1 N4 C9 167.1(3) . . . . ?
N1 Co1 N5 C12 -41.7(3) . . . . ?
N1 Co1 N5 C16 139.3(3) . . . . ?
N1 Co1 N6 C21 120.7(3) . . . . ?
N1 Co1 N6 C25 -56.3(3) . . . . ?
N1 C1 C2 N2 1.4(5) . . . . ?
N1 C1 C2 C4 -176.5(4) . . . . ?
N2 Co1 N1 O2 -175.4(3) . . . . ?
N2 Co1 N1 C1 10.6(3) . . . . ?
N2 Co1 N3 C7 7.9(3) . . . . ?
N2 Co1 N3 C8 -168.5(3) . . . . ?
N2 Co1 N4 O1 -70(4) . . . . ?
N2 Co1 N4 C9 106(4) . . . . ?
N2 Co1 N5 C12 39.6(3) . . . . ?
N2 Co1 N5 C16 -139.4(3) . . . . ?
N2 Co1 N6 C21 39.5(3) . . . . ?
N2 Co1 N6 C25 -137.5(3) . . . . ?
N2 C5 C6 C7 64.6(5) . . . . ?
N3 Co1 N1 O2 89.9(19) . . . . ?
N3 Co1 N1 C1 -84.1(19) . . . . ?
N3 Co1 N2 C2 166.2(3) . . . . ?
N3 Co1 N2 C5 -11.9(3) . . . . ?
N3 Co1 N4 O1 174.9(3) . . . . ?
N3 Co1 N4 C9 -8.6(3) . . . . ?
N3 Co1 N5 C12 138.8(3) . . . . ?
N3 Co1 N5 C16 -40.2(3) . . . . ?
N3 Co1 N6 C21 -59.6(3) . . . . ?
N3 Co1 N6 C25 123.3(3) . . . . ?
N3 C8 C9 N4 1.9(5) . . . . ?
N3 C8 C9 C11 -175.7(4) . . . . ?
N4 Co1 N1 O2 6.6(3) . . . . ?
N4 Co1 N1 C1 -167.4(3) . . . . ?
N4 Co1 N2 C2 52(4) . . . . ?
N4 Co1 N2 C5 -126(4) . . . . ?
N4 Co1 N3 C7 -174.2(3) . . . . ?
N4 Co1 N3 C8 9.4(3) . . . . ?
N4 Co1 N5 C12 -139.4(3) . . . . ?
N4 Co1 N5 C16 41.6(3) . . . . ?
N4 Co1 N6 C21 -141.4(3) . . . . ?
N4 Co1 N6 C25 41.5(3) . . . . ?
N5 Co1 N1 O2 -83.9(3) . . . . ?
N5 Co1 N1 C1 102.0(3) . . . . ?
N5 Co1 N2 C2 -101.1(3) . . . . ?
N5 Co1 N2 C5 80.8(3) . . . . ?
N5 Co1 N3 C7 -84.2(3) . . . . ?
N5 Co1 N3 C8 99.4(3) . . . . ?
N5 Co1 N4 O1 82.5(3) . . . . ?
N5 Co1 N4 C9 -101.0(3) . . . . ?
N5 Co1 N6 C21 170(3) . . . . ?
N5 Co1 N6 C25 -7(3) . . . . ?
N5 C12 C13 C14 -0.7(6) . . . . ?
N6 Co1 N1 O2 94.2(3) . . . . ?
N6 Co1 N1 C1 -79.8(3) . . . . ?
N6 Co1 N2 C2 77.0(3) . . . . ?
N6 Co1 N2 C5 -101.0(3) . . . . ?
N6 Co1 N3 C7 97.7(3) . . . . ?
N6 Co1 N3 C8 -78.8(3) . . . . ?
N6 Co1 N4 O1 -95.6(3) . . . . ?
N6 Co1 N4 C9 80.8(3) . . . . ?
N6 Co1 N5 C12 -91(3) . . . . ?
N6 Co1 N5 C16 90(3) . . . . ?
N6 C21 C22 C23 -0.1(7) . . . . ?
C2 N2 C5 C6 162.5(4) . . . . ?
C3 C1 C2 N2 -178.7(4) . . . . ?
C3 C1 C2 C4 3.3(6) . . . . ?
C5 N2 C2 C1 -174.8(3) . . . . ?
C5 N2 C2 C4 3.1(6) . . . . ?
C5 C6 C7 N3 -68.8(5) . . . . ?
C7 N3 C8 C9 174.8(3) . . . . ?
C7 N3 C8 C10 -3.8(6) . . . . ?
C8 N3 C7 C6 -156.9(4) . . . . ?
C10 C8 C9 N4 -179.4(4) . . . . ?
C10 C8 C9 C11 3.1(6) . . . . ?
C12 N5 C16 C15 0.8(5) . . . . ?
C12 C13 C14 C15 1.4(6) . . . . ?
C12 C13 C14 C17 -178.3(4) . . . . ?
C13 C14 C15 C16 -1.1(5) . . . . ?
C13 C14 C17 C18 124.1(4) . . . . ?
C13 C14 C17 C19 7.1(6) . . . . ?
C13 C14 C17 C20 -117.3(5) . . . . ?
C14 C15 C16 N5 0.0(6) . . . . ?
C15 C14 C17 C18 -55.6(5) . . . . ?
C15 C14 C17 C19 -172.7(4) . . . . ?
C15 C14 C17 C20 62.9(5) . . . . ?
C16 N5 C12 C13 -0.4(6) . . . . ?
C17 C14 C15 C16 178.7(4) . . . . ?
C21 N6 C25 C24 0.2(6) . . . . ?
C21 C22 C23 C24 -1.2(6) . . . . ?
C21 C22 C23 C26 178.7(4) . . . . ?
C22 C23 C24 C25 2.0(6) . . . . ?
C22 C23 C26 C27 -55.4(5) . . . . ?
C22 C23 C26 C28 -176.0(4) . . . . ?
C22 C23 C26 C29 63.3(5) . . . . ?
C23 C24 C25 N6 -1.5(7) . . . . ?
C24 C23 C26 C27 124.5(5) . . . . ?
C24 C23 C26 C28 3.9(6) . . . . ?
C24 C23 C26 C29 -116.8(4) . . . . ?
C25 N6 C21 C22 0.6(6) . . . . ?
C26 C23 C24 C25 -177.9(4) . . . . ?

_contact_Crystallographer_email  staples@chemistry.msu.com
_contact_Crystallographer_name   'Richard Staples'
