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

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

data_endo-2
_database_code_depnum_ccdc_archive 'CCDC 1050355'
_audit_update_record             
;
2015-02-18 deposited with the CCDC.
2015-03-12 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;

_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H14 Co2 O7'
_chemical_formula_weight         436.13
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'
O O 0.0106 0.0060 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.893(3)
_cell_length_b                   16.495(6)
_cell_length_c                   19.797(9)
_cell_angle_alpha                101.280(16)
_cell_angle_beta                 102.130(12)
_cell_angle_gamma                103.697(12)
_cell_volume                     2664.9(18)
_cell_formula_units_Z            6
_cell_measurement_temperature    110
_cell_measurement_reflns_used    9914
_cell_measurement_theta_min      2.82
_cell_measurement_theta_max      30.59
_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.631
_exptl_crystal_F_000             1320
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.460
_exptl_crystal_size_mid          0.420
_exptl_crystal_size_min          0.082
_exptl_absorpt_coefficient_mu    1.900
_shelx_estimated_absorpt_T_min   0.475
_shelx_estimated_absorpt_T_max   0.860
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.565
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   SADABS
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      110
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker Kappa Axis Apex2'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            47564
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.933
_diffrn_reflns_theta_max         30.587
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             16299
_reflns_number_gt                14243
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_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.
;

_computing_data_collection       Apex2
_computing_cell_refinement       SAINT
_computing_data_reduction        SAINT
_computing_structure_solution    XS
_computing_structure_refinement  SHELXL-2014
_computing_molecular_graphics    NRCVAX
_computing_publication_material  cif2tables.py
_refine_special_details          
;
 ?
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0279P)²+0.7707P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         16299
_refine_ls_number_parameters     676
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0296
_refine_ls_R_factor_gt           0.0231
_refine_ls_wR_factor_ref         0.0600
_refine_ls_wR_factor_gt          0.0571
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.003
_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_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
Co1A Co 0.71668(2) 0.77052(2) 0.35274(2) 0.01272(4) Uani 1 1 d . . . . .
Co1B Co -0.07929(2) 1.02103(2) 0.13673(2) 0.01276(4) Uani 1 1 d . . . . .
Co1C Co 0.21783(2) 0.54514(2) 0.91876(2) 0.01587(4) Uani 1 1 d . . . . .
O1B O -0.01560(13) 1.11508(7) 0.02848(6) 0.0284(2) Uani 1 1 d . . . . .
O1A O 0.80027(12) 0.76381(7) 0.21490(5) 0.0244(2) Uani 1 1 d . . . . .
C1B C -0.04448(14) 1.07567(9) 0.06766(7) 0.0183(2) Uani 1 1 d . . . . .
C1A C 0.76767(14) 0.76617(8) 0.26744(7) 0.0164(2) Uani 1 1 d . . . . .
O1C O -0.13131(13) 0.46565(9) 0.88487(7) 0.0440(3) Uani 1 1 d . . . . .
C1C C 0.00394(17) 0.49526(9) 0.90056(8) 0.0252(3) Uani 1 1 d . . . . .
Co2B Co 0.19334(2) 1.00770(2) 0.18062(2) 0.01324(4) Uani 1 1 d . . . . .
Co2A Co 0.50684(2) 0.84564(2) 0.33377(2) 0.01538(4) Uani 1 1 d . . . . .
Co2C Co 0.24977(2) 0.69442(2) 0.98555(2) 0.01441(4) Uani 1 1 d . . . . .
O2A O 0.98501(13) 0.91248(7) 0.45456(6) 0.0313(2) Uani 1 1 d . . . . .
O2B O -0.34986(11) 1.07734(7) 0.16901(6) 0.0281(2) Uani 1 1 d . . . . .
O2C O 0.37317(13) 0.49268(8) 1.04315(6) 0.0323(2) Uani 1 1 d . . . . .
C2B C -0.24611(14) 1.05464(8) 0.15558(7) 0.0179(2) Uani 1 1 d . . . . .
C2C C 0.31458(16) 0.51253(9) 0.99499(8) 0.0227(3) Uani 1 1 d . . . . .
C2A C 0.88120(15) 0.85816(8) 0.41606(7) 0.0186(2) Uani 1 1 d . . . . .
O3B O -0.24900(13) 0.83596(7) 0.06905(6) 0.0311(2) Uani 1 1 d . . . . .
C3B C -0.18376(15) 0.90686(9) 0.09430(7) 0.0197(2) Uani 1 1 d . . . . .
C3A C 0.77756(15) 0.67877(9) 0.36997(7) 0.0195(2) Uani 1 1 d . . . . .
O3C O 0.29645(18) 0.43372(8) 0.80552(7) 0.0436(3) Uani 1 1 d . . . . .
O3A O 0.81676(14) 0.62009(7) 0.37887(6) 0.0314(2) Uani 1 1 d . . . . .
C3C C 0.26491(18) 0.47615(9) 0.84982(9) 0.0270(3) Uani 1 1 d . . . . .
O4B O 0.32317(11) 1.06526(7) 0.06667(5) 0.0259(2) Uani 1 1 d . . . . .
O4A O 0.54727(13) 0.88724(7) 0.19901(6) 0.0290(2) Uani 1 1 d . . . . .
C4B C 0.27514(14) 1.04149(8) 0.11001(7) 0.0182(2) Uani 1 1 d . . . . .
C4A C 0.53085(15) 0.87084(9) 0.25063(8) 0.0203(3) Uani 1 1 d . . . . .
O4C O 0.45077(15) 0.69096(8) 1.12347(6) 0.0411(3) Uani 1 1 d . . . . .
C4C C 0.37211(17) 0.69239(9) 1.07106(8) 0.0244(3) Uani 1 1 d . . . . .
C5B C 0.15242(15) 0.89019(9) 0.15977(7) 0.0204(2) Uani 1 1 d . . . . .
C5A C 0.59456(16) 0.94563(9) 0.40485(8) 0.0234(3) Uani 1 1 d . . . . .
O5B O 0.12686(14) 0.81775(7) 0.14848(6) 0.0332(2) Uani 1 1 d . . . . .
C5C C 0.04672(17) 0.68384(9) 0.99468(8) 0.0252(3) Uani 1 1 d . . . . .
O5C O -0.08117(13) 0.67612(8) 0.99734(8) 0.0450(3) Uani 1 1 d . . . . .
O5A O 0.64357(15) 1.00503(8) 0.45181(7) 0.0395(3) Uani 1 1 d . . . . .
O6A O 0.16576(13) 0.82529(9) 0.32018(8) 0.0431(3) Uani 1 1 d . . . . .
O6B O 0.48410(12) 1.07294(7) 0.30021(6) 0.0313(2) Uani 1 1 d . . . . .
O6C O 0.37854(14) 0.87953(7) 0.99992(7) 0.0363(3) Uani 1 1 d . . . . .
C6C C 0.32494(16) 0.80801(9) 0.99471(8) 0.0217(3) Uani 1 1 d . . . . .
C6B C 0.37300(15) 1.04470(8) 0.25281(7) 0.0193(2) Uani 1 1 d . . . . .
C6A C 0.29819(16) 0.83553(10) 0.32416(8) 0.0255(3) Uani 1 1 d . . . . .
O7A O 0.26833(10) 0.45007(6) 0.49540(5) 0.01746(17) Uani 0.5 1 d . . P A 1
H7AA H 0.2668 0.4940 0.5247 0.026 Uiso 0.5 1 d R U P A 1
O7A' O 0.26833(10) 0.45007(6) 0.49540(5) 0.01746(17) Uani 0.5 1 d . . P A 2
H7A' H 0.1754 0.4156 0.4779 0.026 Uiso 0.5 1 d R U P A 2
O7B O -0.03259(11) 1.33842(6) 0.43876(6) 0.0238(2) Uani 0.5 1 d . . P B 1
H7BA H -0.1147 1.3543 0.4259 0.036 Uiso 0.5 1 d R U P B 1
O7B' O -0.03259(11) 1.33842(6) 0.43876(6) 0.0238(2) Uani 0.5 1 d . . P B 2
H7B' H 0.0603 1.3729 0.4562 0.036 Uiso 0.5 1 d R U P B 2
C7C C 0.20373(13) 0.64661(8) 0.88198(6) 0.0142(2) Uani 1 1 d . . . . .
C7B C 0.10016(13) 1.09883(7) 0.21643(6) 0.0122(2) Uani 1 1 d . . . . .
C7A C 0.52921(13) 0.76431(8) 0.39298(7) 0.0142(2) Uani 1 1 d . . . . .
C8A C 0.48236(13) 0.72080(8) 0.32394(7) 0.0149(2) Uani 1 1 d . . . . .
C8B C 0.03800(13) 1.02698(7) 0.23522(6) 0.0125(2) Uani 1 1 d . . . . .
C8C C 0.35764(13) 0.65594(8) 0.91388(6) 0.0134(2) Uani 1 1 d . . . . .
C9B C -0.01470(14) 0.99531(8) 0.29469(7) 0.0157(2) Uani 1 1 d . . . . .
H9BA H 0.0738 0.9791 0.3231 0.019 Uiso 1 1 calc R U . . .
H9BB H -0.1075 0.9428 0.2740 0.019 Uiso 1 1 calc R U . . .
C9A C 0.37436(15) 0.63824(8) 0.27239(7) 0.0193(2) Uani 1 1 d . . . . .
H9AA H 0.4268 0.6204 0.2349 0.023 Uiso 1 1 calc R U . . .
H9AB H 0.2730 0.6482 0.2488 0.023 Uiso 1 1 calc R U . . .
C9C C 0.52399(13) 0.68258(8) 0.90552(7) 0.0153(2) Uani 1 1 d . . . . .
H9CA H 0.5920 0.6546 0.9336 0.018 Uiso 1 1 calc R U . . .
H9CB H 0.5699 0.7459 0.9251 0.018 Uiso 1 1 calc R U . . .
C10C C 0.52838(13) 0.65835(8) 0.82709(7) 0.0155(2) Uani 1 1 d . . . . .
H10A H 0.6402 0.6619 0.8254 0.019 Uiso 1 1 calc R U . . .
H10B H 0.4617 0.5979 0.8043 0.019 Uiso 1 1 calc R U . . .
C10B C -0.06259(14) 1.06261(8) 0.34446(7) 0.0151(2) Uani 1 1 d . . . . .
H10C H -0.1348 1.0878 0.3154 0.018 Uiso 1 1 calc R U . . .
H10D H -0.1221 1.0340 0.3745 0.018 Uiso 1 1 calc R U . . .
C10A C 0.33533(15) 0.56499(8) 0.30934(7) 0.0179(2) Uani 1 1 d . . . . .
H10E H 0.2901 0.5090 0.2727 0.022 Uiso 1 1 calc R U . . .
H10F H 0.4357 0.5634 0.3414 0.022 Uiso 1 1 calc R U . . .
C11B C 0.08337(14) 1.13390(8) 0.39204(6) 0.0146(2) Uani 1 1 d . . . . .
H11A H 0.1647 1.1121 0.4204 0.017 Uiso 1 1 calc R U . . .
C11C C 0.46722(13) 0.71710(8) 0.78541(6) 0.0139(2) Uani 1 1 d . . . . .
H11B H 0.5296 0.7793 0.8062 0.017 Uiso 1 1 calc R U . . .
C11A C 0.21670(14) 0.57690(8) 0.35236(7) 0.0168(2) Uani 1 1 d . . . . .
H11C H 0.1150 0.5831 0.3237 0.020 Uiso 1 1 calc R U . . .
C12A C 0.26540(14) 0.62808(8) 0.43006(7) 0.0150(2) Uani 1 1 d . . . . .
H12A H 0.1896 0.6611 0.4421 0.018 Uiso 1 1 calc R U . . .
C12B C 0.15777(13) 1.21442(8) 0.37081(6) 0.0133(2) Uani 1 1 d . . . . .
H12B H 0.2778 1.2347 0.3875 0.016 Uiso 1 1 calc R U . . .
C12C C 0.29216(13) 0.70431(8) 0.74928(6) 0.0134(2) Uani 1 1 d . . . . .
H12C H 0.2644 0.7599 0.7516 0.016 Uiso 1 1 calc R U . . .
C13B C 0.08933(13) 1.23187(7) 0.30033(6) 0.0129(2) Uani 1 1 d . . . . .
H13A H 0.1117 1.2950 0.3065 0.015 Uiso 1 1 calc R U . . .
H13B H -0.0287 1.2058 0.2853 0.015 Uiso 1 1 calc R U . . .
C13C C 0.15438(13) 0.63099(8) 0.74985(6) 0.0152(2) Uani 1 1 d . . . . .
H13C H 0.1898 0.5784 0.7495 0.018 Uiso 1 1 calc R U . . .
H13D H 0.0652 0.6186 0.7063 0.018 Uiso 1 1 calc R U . . .
C13A C 0.43797(13) 0.67161(8) 0.47307(7) 0.0146(2) Uani 1 1 d . . . . .
H13E H 0.5066 0.6366 0.4574 0.017 Uiso 1 1 calc R U . . .
H13F H 0.4466 0.6747 0.5242 0.017 Uiso 1 1 calc R U . . .
C14A C 0.49888(14) 0.76310(8) 0.46428(7) 0.0159(2) Uani 1 1 d . . . . .
H14A H 0.4186 0.7943 0.4711 0.019 Uiso 1 1 calc R U . . .
H14B H 0.5998 0.7944 0.5021 0.019 Uiso 1 1 calc R U . . .
C14C C 0.09494(14) 0.65422(9) 0.81649(7) 0.0178(2) Uani 1 1 d . . . . .
H14C H 0.0878 0.7142 0.8238 0.021 Uiso 1 1 calc R U . . .
H14D H -0.0142 0.6154 0.8087 0.021 Uiso 1 1 calc R U . . .
C14B C 0.16179(13) 1.19460(7) 0.24198(6) 0.0137(2) Uani 1 1 d . . . . .
H14E H 0.1369 1.2198 0.2010 0.016 Uiso 1 1 calc R U . . .
H14F H 0.2801 1.2116 0.2610 0.016 Uiso 1 1 calc R U . . .
C15A C 0.19203(14) 0.53100(8) 0.41012(7) 0.0156(2) Uani 1 1 d . . . . .
H15A H 0.0778 0.5121 0.4119 0.019 Uiso 1 1 calc R U . . .
C15B C 0.07649(14) 1.22102(8) 0.43077(7) 0.0158(2) Uani 1 1 d . . . . .
H15B H 0.1530 1.2449 0.4796 0.019 Uiso 1 1 calc R U . . .
C15C C 0.40783(14) 0.69315(8) 0.70435(7) 0.0147(2) Uani 1 1 d . . . . .
H15C H 0.4401 0.7418 0.6822 0.018 Uiso 1 1 calc R U . . .
C16C C 0.39374(15) 0.60584(8) 0.65932(7) 0.0178(2) Uani 1 1 d . . . . .
H16A H 0.4966 0.6055 0.6477 0.021 Uiso 1 1 calc R U . C 1
H16B H 0.3680 0.5614 0.6856 0.021 Uiso 1 1 calc R U . C 1
C16B C -0.07592(15) 1.24669(8) 0.42364(7) 0.0172(2) Uani 1 1 d . . . . .
H16C H -0.1473 1.2206 0.3745 0.021 Uiso 1 1 calc R U . B 1
H16D H -0.1335 1.2265 0.4577 0.021 Uiso 1 1 calc R U . B 1
C16A C 0.28883(14) 0.47155(8) 0.43017(7) 0.0164(2) Uani 1 1 d . . . . .
H16E H 0.2547 0.4179 0.3911 0.020 Uiso 1 1 calc R U . A 1
H16F H 0.4039 0.4998 0.4363 0.020 Uiso 1 1 calc R U . A 1
O7C O 0.26878(12) 0.58776(6) 0.59537(5) 0.02192(19) Uani 0.5 1 d . . P D 1
H7CA H 0.2149 0.6230 0.6001 0.033 Uiso 0.5 1 d R U P D 1
O7C' O 0.26878(12) 0.58776(6) 0.59537(5) 0.02192(19) Uani 0.5 1 d . . P D 2
H7C' H 0.2685 0.5450 0.5643 0.033 Uiso 0.5 1 d R U P D 2


_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
Co1A C3A 1.7923(14) . ?
Co1A C2A 1.8223(15) . ?
Co1A C1A 1.8311(15) . ?
Co1A C8A 1.9617(13) . ?
Co1A C7A 1.9835(13) . ?
Co1A Co2A 2.4782(7) . ?
Co1B C2B 1.7857(13) . ?
Co1B C1B 1.8181(15) . ?
Co1B C3B 1.8275(15) . ?
Co1B C7B 1.9655(13) . ?
Co1B C8B 1.9804(14) . ?
Co1B Co2B 2.4747(8) . ?
Co1C C3C 1.7864(16) . ?
Co1C C1C 1.8111(15) . ?
Co1C C2C 1.8162(16) . ?
Co1C C7C 1.9709(14) . ?
Co1C C8C 1.9846(13) . ?
Co1C Co2C 2.4757(9) . ?
O1B C1B 1.1366(17) . ?
O1A C1A 1.1329(17) . ?
O1C C1C 1.1345(18) . ?
Co2B C6B 1.7904(14) . ?
Co2B C4B 1.8258(15) . ?
Co2B C5B 1.8302(16) . ?
Co2B C7B 1.9669(12) . ?
Co2B C8B 1.9697(12) . ?
Co2A C6A 1.7888(15) . ?
Co2A C4A 1.8167(16) . ?
Co2A C5A 1.8250(16) . ?
Co2A C7A 1.9639(13) . ?
Co2A C8A 1.9847(14) . ?
Co2C C6C 1.7926(16) . ?
Co2C C4C 1.8210(16) . ?
Co2C C5C 1.8233(15) . ?
Co2C C8C 1.9607(13) . ?
Co2C C7C 1.9635(15) . ?
O2A C2A 1.1320(17) . ?
O2B C2B 1.1357(16) . ?
O2C C2C 1.1322(18) . ?
O3B C3B 1.1324(17) . ?
C3A O3A 1.1358(17) . ?
O3C C3C 1.1376(19) . ?
O4B C4B 1.1309(17) . ?
O4A C4A 1.1363(17) . ?
O4C C4C 1.1310(18) . ?
C5B O5B 1.1291(18) . ?
C5A O5A 1.1336(19) . ?
C5C O5C 1.1277(18) . ?
O6A C6A 1.1328(18) . ?
O6B C6B 1.1379(17) . ?
O6C C6C 1.1379(18) . ?
O7A C16A 1.4401(16) . ?
O7A H7AA 0.8401 . ?
O7B C16B 1.4232(16) . ?
O7B H7BA 0.8401 . ?
C7C C8C 1.3397(16) . ?
C7C C14C 1.4922(17) . ?
C7B C8B 1.3406(17) . ?
C7B C14B 1.4875(17) . ?
C7A C8A 1.3387(18) . ?
C7A C14A 1.4946(18) . ?
C8A C9A 1.4979(18) . ?
C8B C9B 1.4951(17) . ?
C8C C9C 1.4941(16) . ?
C9B C10B 1.5353(17) . ?
C9B H9BA 0.9900 . ?
C9B H9BB 0.9900 . ?
C9A C10A 1.5392(18) . ?
C9A H9AA 0.9900 . ?
C9A H9AB 0.9900 . ?
C9C C10C 1.5370(19) . ?
C9C H9CA 0.9900 . ?
C9C H9CB 0.9900 . ?
C10C C11C 1.5132(17) . ?
C10C H10A 0.9900 . ?
C10C H10B 0.9900 . ?
C10B C11B 1.5116(17) . ?
C10B H10C 0.9900 . ?
C10B H10D 0.9900 . ?
C10A C11A 1.5123(18) . ?
C10A H10E 0.9900 . ?
C10A H10F 0.9900 . ?
C11B C15B 1.5123(17) . ?
C11B C12B 1.5157(17) . ?
C11B H11A 1.0000 . ?
C11C C12C 1.5157(16) . ?
C11C C15C 1.5190(18) . ?
C11C H11B 1.0000 . ?
C11A C15A 1.5148(18) . ?
C11A C12A 1.5183(19) . ?
C11A H11C 1.0000 . ?
C12A C13A 1.5119(17) . ?
C12A C15A 1.5149(18) . ?
C12A H12A 1.0000 . ?
C12B C13B 1.5111(17) . ?
C12B C15B 1.5135(17) . ?
C12B H12B 1.0000 . ?
C12C C13C 1.5079(17) . ?
C12C C15C 1.5145(17) . ?
C12C H12C 1.0000 . ?
C13B C14B 1.5331(17) . ?
C13B H13A 0.9900 . ?
C13B H13B 0.9900 . ?
C13C C14C 1.5356(18) . ?
C13C H13C 0.9900 . ?
C13C H13D 0.9900 . ?
C13A C14A 1.5352(17) . ?
C13A H13E 0.9900 . ?
C13A H13F 0.9900 . ?
C14A H14A 0.9900 . ?
C14A H14B 0.9900 . ?
C14C H14C 0.9900 . ?
C14C H14D 0.9900 . ?
C14B H14E 0.9900 . ?
C14B H14F 0.9900 . ?
C15A C16A 1.5062(18) . ?
C15A H15A 1.0000 . ?
C15B C16B 1.5004(17) . ?
C15B H15B 1.0000 . ?
C15C C16C 1.4999(18) . ?
C15C H15C 1.0000 . ?
C16C O7C 1.4250(16) . ?
C16C H16A 0.9900 . ?
C16C H16B 0.9900 . ?
C16B H16C 0.9900 . ?
C16B H16D 0.9900 . ?
C16A H16E 0.9900 . ?
C16A H16F 0.9900 . ?
O7C H7CA 0.8400 . ?

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
C3A Co1A C2A 100.62(6) . . ?
C3A Co1A C1A 96.76(6) . . ?
C2A Co1A C1A 103.74(6) . . ?
C3A Co1A C8A 100.21(6) . . ?
C2A Co1A C8A 143.27(6) . . ?
C1A Co1A C8A 103.44(6) . . ?
C3A Co1A C7A 102.82(6) . . ?
C2A Co1A C7A 105.87(6) . . ?
C1A Co1A C7A 140.48(5) . . ?
C8A Co1A C7A 39.67(5) . . ?
C3A Co1A Co2A 150.32(4) . . ?
C2A Co1A Co2A 100.09(5) . . ?
C1A Co1A Co2A 98.72(4) . . ?
C8A Co1A Co2A 51.51(4) . . ?
C7A Co1A Co2A 50.76(4) . . ?
C2B Co1B C1B 99.97(6) . . ?
C2B Co1B C3B 98.44(6) . . ?
C1B Co1B C3B 108.75(7) . . ?
C2B Co1B C7B 101.91(6) . . ?
C1B Co1B C7B 98.38(6) . . ?
C3B Co1B C7B 142.48(5) . . ?
C2B Co1B C8B 99.12(6) . . ?
C1B Co1B C8B 136.91(6) . . ?
C3B Co1B C8B 106.13(6) . . ?
C7B Co1B C8B 39.72(5) . . ?
C2B Co1B Co2B 148.99(4) . . ?
C1B Co1B Co2B 99.07(4) . . ?
C3B Co1B Co2B 98.31(4) . . ?
C7B Co1B Co2B 51.03(4) . . ?
C8B Co1B Co2B 51.02(3) . . ?
C3C Co1C C1C 100.92(7) . . ?
C3C Co1C C2C 98.78(7) . . ?
C1C Co1C C2C 106.59(7) . . ?
C3C Co1C C7C 103.98(7) . . ?
C1C Co1C C7C 97.19(6) . . ?
C2C Co1C C7C 143.12(6) . . ?
C3C Co1C C8C 97.17(6) . . ?
C1C Co1C C8C 136.33(6) . . ?
C2C Co1C C8C 109.44(6) . . ?
C7C Co1C C8C 39.59(5) . . ?
C3C Co1C Co2C 147.71(5) . . ?
C1C Co1C Co2C 102.13(5) . . ?
C2C Co1C Co2C 95.96(5) . . ?
C7C Co1C Co2C 50.87(4) . . ?
C8C Co1C Co2C 50.70(4) . . ?
O1B C1B Co1B 174.86(12) . . ?
O1A C1A Co1A 179.53(13) . . ?
O1C C1C Co1C 175.29(15) . . ?
C6B Co2B C4B 99.68(7) . . ?
C6B Co2B C5B 102.86(6) . . ?
C4B Co2B C5B 105.90(6) . . ?
C6B Co2B C7B 95.48(6) . . ?
C4B Co2B C7B 104.90(6) . . ?
C5B Co2B C7B 140.63(6) . . ?
C6B Co2B C8B 99.05(6) . . ?
C4B Co2B C8B 141.46(5) . . ?
C5B Co2B C8B 102.30(6) . . ?
C7B Co2B C8B 39.82(5) . . ?
C6B Co2B Co1B 145.52(4) . . ?
C4B Co2B Co1B 97.23(4) . . ?
C5B Co2B Co1B 101.05(4) . . ?
C7B Co2B Co1B 50.97(4) . . ?
C8B Co2B Co1B 51.40(4) . . ?
C6A Co2A C4A 101.23(6) . . ?
C6A Co2A C5A 99.66(7) . . ?
C4A Co2A C5A 107.58(7) . . ?
C6A Co2A C7A 98.12(6) . . ?
C4A Co2A C7A 144.57(6) . . ?
C5A Co2A C7A 97.98(7) . . ?
C6A Co2A C8A 94.79(6) . . ?
C4A Co2A C8A 108.94(6) . . ?
C5A Co2A C8A 136.99(6) . . ?
C7A Co2A C8A 39.63(5) . . ?
C6A Co2A Co1A 144.55(5) . . ?
C4A Co2A Co1A 98.39(4) . . ?
C5A Co2A Co1A 102.16(5) . . ?
C7A Co2A Co1A 51.46(4) . . ?
C8A Co2A Co1A 50.69(4) . . ?
C6C Co2C C4C 97.11(7) . . ?
C6C Co2C C5C 102.17(6) . . ?
C4C Co2C C5C 106.85(7) . . ?
C6C Co2C C8C 96.95(6) . . ?
C4C Co2C C8C 105.96(7) . . ?
C5C Co2C C8C 139.31(6) . . ?
C6C Co2C C7C 102.03(6) . . ?
C4C Co2C C7C 142.28(6) . . ?
C5C Co2C C7C 100.50(6) . . ?
C8C Co2C C7C 39.92(5) . . ?
C6C Co2C Co1C 147.89(5) . . ?
C4C Co2C Co1C 97.94(5) . . ?
C5C Co2C Co1C 100.34(5) . . ?
C8C Co2C Co1C 51.56(4) . . ?
C7C Co2C Co1C 51.14(4) . . ?
O2B C2B Co1B 178.39(13) . . ?
O2C C2C Co1C 178.81(13) . . ?
O2A C2A Co1A 178.78(13) . . ?
O3B C3B Co1B 178.87(13) . . ?
O3A C3A Co1A 177.93(13) . . ?
O3C C3C Co1C 178.53(14) . . ?
O4B C4B Co2B 177.11(12) . . ?
O4A C4A Co2A 179.30(14) . . ?
O4C C4C Co2C 178.46(15) . . ?
O5B C5B Co2B 178.40(13) . . ?
O5A C5A Co2A 175.33(13) . . ?
O5C C5C Co2C 177.16(15) . . ?
O6C C6C Co2C 177.05(12) . . ?
O6B C6B Co2B 175.45(12) . . ?
O6A C6A Co2A 175.85(14) . . ?
C16A O7A H7AA 109.6 . . ?
C16B O7B H7BA 109.7 . . ?
C8C C7C C14C 143.37(11) . . ?
C8C C7C Co2C 69.93(7) . . ?
C14C C7C Co2C 136.04(9) . . ?
C8C C7C Co1C 70.75(7) . . ?
C14C C7C Co1C 130.82(9) . . ?
Co2C C7C Co1C 77.99(5) . . ?
C8B C7B C14B 143.74(11) . . ?
C8B C7B Co1B 70.74(7) . . ?
C14B C7B Co1B 132.38(8) . . ?
C8B C7B Co2B 70.20(7) . . ?
C14B C7B Co2B 134.00(8) . . ?
Co1B C7B Co2B 78.00(5) . . ?
C8A C7A C14A 143.65(11) . . ?
C8A C7A Co2A 71.02(8) . . ?
C14A C7A Co2A 130.99(9) . . ?
C8A C7A Co1A 69.29(7) . . ?
C14A C7A Co1A 136.01(8) . . ?
Co2A C7A Co1A 77.78(5) . . ?
C7A C8A C9A 143.05(11) . . ?
C7A C8A Co1A 71.04(7) . . ?
C9A C8A Co1A 131.95(9) . . ?
C7A C8A Co2A 69.35(7) . . ?
C9A C8A Co2A 135.61(9) . . ?
Co1A C8A Co2A 77.80(5) . . ?
C7B C8B C9B 143.01(11) . . ?
C7B C8B Co2B 69.98(7) . . ?
C9B C8B Co2B 135.59(8) . . ?
C7B C8B Co1B 69.54(7) . . ?
C9B C8B Co1B 132.65(9) . . ?
Co2B C8B Co1B 77.58(5) . . ?
C7C C8C C9C 142.77(12) . . ?
C7C C8C Co2C 70.15(8) . . ?
C9C C8C Co2C 135.05(9) . . ?
C7C C8C Co1C 69.65(7) . . ?
C9C C8C Co1C 133.19(9) . . ?
Co2C C8C Co1C 77.73(5) . . ?
C8B C9B C10B 113.02(10) . . ?
C8B C9B H9BA 109.0 . . ?
C10B C9B H9BA 109.0 . . ?
C8B C9B H9BB 109.0 . . ?
C10B C9B H9BB 109.0 . . ?
H9BA C9B H9BB 107.8 . . ?
C8A C9A C10A 112.23(11) . . ?
C8A C9A H9AA 109.2 . . ?
C10A C9A H9AA 109.2 . . ?
C8A C9A H9AB 109.2 . . ?
C10A C9A H9AB 109.2 . . ?
H9AA C9A H9AB 107.9 . . ?
C8C C9C C10C 112.52(10) . . ?
C8C C9C H9CA 109.1 . . ?
C10C C9C H9CA 109.1 . . ?
C8C C9C H9CB 109.1 . . ?
C10C C9C H9CB 109.1 . . ?
H9CA C9C H9CB 107.8 . . ?
C11C C10C C9C 112.01(10) . . ?
C11C C10C H10A 109.2 . . ?
C9C C10C H10A 109.2 . . ?
C11C C10C H10B 109.2 . . ?
C9C C10C H10B 109.2 . . ?
H10A C10C H10B 107.9 . . ?
C11B C10B C9B 111.28(10) . . ?
C11B C10B H10C 109.4 . . ?
C9B C10B H10C 109.4 . . ?
C11B C10B H10D 109.4 . . ?
C9B C10B H10D 109.4 . . ?
H10C C10B H10D 108.0 . . ?
C11A C10A C9A 111.78(11) . . ?
C11A C10A H10E 109.3 . . ?
C9A C10A H10E 109.3 . . ?
C11A C10A H10F 109.3 . . ?
C9A C10A H10F 109.3 . . ?
H10E C10A H10F 107.9 . . ?
C10B C11B C15B 123.74(10) . . ?
C10B C11B C12B 123.61(10) . . ?
C15B C11B C12B 59.98(8) . . ?
C10B C11B H11A 113.2 . . ?
C15B C11B H11A 113.2 . . ?
C12B C11B H11A 113.2 . . ?
C10C C11C C12C 124.91(10) . . ?
C10C C11C C15C 123.38(11) . . ?
C12C C11C C15C 59.87(8) . . ?
C10C C11C H11B 112.9 . . ?
C12C C11C H11B 112.9 . . ?
C15C C11C H11B 112.9 . . ?
C10A C11A C15A 123.15(11) . . ?
C10A C11A C12A 123.68(10) . . ?
C15A C11A C12A 59.93(9) . . ?
C10A C11A H11C 113.3 . . ?
C15A C11A H11C 113.3 . . ?
C12A C11A H11C 113.3 . . ?
C13A C12A C15A 122.43(10) . . ?
C13A C12A C11A 123.59(10) . . ?
C15A C12A C11A 59.92(8) . . ?
C13A C12A H12A 113.6 . . ?
C15A C12A H12A 113.6 . . ?
C11A C12A H12A 113.6 . . ?
C13B C12B C15B 122.15(10) . . ?
C13B C12B C11B 122.74(10) . . ?
C15B C12B C11B 59.90(8) . . ?
C13B C12B H12B 113.9 . . ?
C15B C12B H12B 113.9 . . ?
C11B C12B H12B 113.9 . . ?
C13C C12C C15C 123.13(10) . . ?
C13C C12C C11C 124.61(10) . . ?
C15C C12C C11C 60.17(8) . . ?
C13C C12C H12C 113.0 . . ?
C15C C12C H12C 113.0 . . ?
C11C C12C H12C 113.0 . . ?
C12B C13B C14B 111.48(10) . . ?
C12B C13B H13A 109.3 . . ?
C14B C13B H13A 109.3 . . ?
C12B C13B H13B 109.3 . . ?
C14B C13B H13B 109.3 . . ?
H13A C13B H13B 108.0 . . ?
C12C C13C C14C 110.51(10) . . ?
C12C C13C H13C 109.5 . . ?
C14C C13C H13C 109.5 . . ?
C12C C13C H13D 109.5 . . ?
C14C C13C H13D 109.5 . . ?
H13C C13C H13D 108.1 . . ?
C12A C13A C14A 111.71(10) . . ?
C12A C13A H13E 109.3 . . ?
C14A C13A H13E 109.3 . . ?
C12A C13A H13F 109.3 . . ?
C14A C13A H13F 109.3 . . ?
H13E C13A H13F 107.9 . . ?
C7A C14A C13A 113.39(10) . . ?
C7A C14A H14A 108.9 . . ?
C13A C14A H14A 108.9 . . ?
C7A C14A H14B 108.9 . . ?
C13A C14A H14B 108.9 . . ?
H14A C14A H14B 107.7 . . ?
C7C C14C C13C 112.00(10) . . ?
C7C C14C H14C 109.2 . . ?
C13C C14C H14C 109.2 . . ?
C7C C14C H14D 109.2 . . ?
C13C C14C H14D 109.2 . . ?
H14C C14C H14D 107.9 . . ?
C7B C14B C13B 112.74(10) . . ?
C7B C14B H14E 109.0 . . ?
C13B C14B H14E 109.0 . . ?
C7B C14B H14F 109.0 . . ?
C13B C14B H14F 109.0 . . ?
H14E C14B H14F 107.8 . . ?
C16A C15A C11A 121.74(10) . . ?
C16A C15A C12A 121.77(10) . . ?
C11A C15A C12A 60.15(8) . . ?
C16A C15A H15A 114.2 . . ?
C11A C15A H15A 114.2 . . ?
C12A C15A H15A 114.2 . . ?
C16B C15B C11B 123.23(11) . . ?
C16B C15B C12B 121.52(11) . . ?
C11B C15B C12B 60.12(8) . . ?
C16B C15B H15B 113.9 . . ?
C11B C15B H15B 113.9 . . ?
C12B C15B H15B 113.9 . . ?
C16C C15C C12C 120.74(10) . . ?
C16C C15C C11C 122.13(11) . . ?
C12C C15C C11C 59.95(8) . . ?
C16C C15C H15C 114.4 . . ?
C12C C15C H15C 114.4 . . ?
C11C C15C H15C 114.4 . . ?
O7C C16C C15C 107.97(10) . . ?
O7C C16C H16A 110.1 . . ?
C15C C16C H16A 110.1 . . ?
O7C C16C H16B 110.1 . . ?
C15C C16C H16B 110.1 . . ?
H16A C16C H16B 108.4 . . ?
O7B C16B C15B 107.35(10) . . ?
O7B C16B H16C 110.2 . . ?
C15B C16B H16C 110.2 . . ?
O7B C16B H16D 110.2 . . ?
C15B C16B H16D 110.2 . . ?
H16C C16B H16D 108.5 . . ?
O7A C16A C15A 111.35(10) . . ?
O7A C16A H16E 109.4 . . ?
C15A C16A H16E 109.4 . . ?
O7A C16A H16F 109.4 . . ?
C15A C16A H16F 109.4 . . ?
H16E C16A H16F 108.0 . . ?
C16C O7C H7CA 109.7 . . ?

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
C14A C7A C8A C9A -5.6(3) . . . . ?
Co2A C7A C8A C9A -140.30(18) . . . . ?
Co1A C7A C8A C9A 135.98(19) . . . . ?
C14A C7A C8A Co1A -141.62(18) . . . . ?
Co2A C7A C8A Co1A 83.72(4) . . . . ?
C14A C7A C8A Co2A 134.66(18) . . . . ?
Co1A C7A C8A Co2A -83.72(4) . . . . ?
C14B C7B C8B C9B 2.0(3) . . . . ?
Co1B C7B C8B C9B -134.96(17) . . . . ?
Co2B C7B C8B C9B 141.26(17) . . . . ?
C14B C7B C8B Co2B -139.25(17) . . . . ?
Co1B C7B C8B Co2B 83.78(4) . . . . ?
C14B C7B C8B Co1B 136.97(17) . . . . ?
Co2B C7B C8B Co1B -83.78(4) . . . . ?
C14C C7C C8C C9C 2.2(3) . . . . ?
Co2C C7C C8C C9C -140.21(19) . . . . ?
Co1C C7C C8C C9C 135.93(18) . . . . ?
C14C C7C C8C Co2C 142.45(19) . . . . ?
Co1C C7C C8C Co2C -83.85(4) . . . . ?
C14C C7C C8C Co1C -133.69(19) . . . . ?
Co2C C7C C8C Co1C 83.85(4) . . . . ?
C7B C8B C9B C10B 24.8(2) . . . . ?
Co2B C8B C9B C10B 147.58(10) . . . . ?
Co1B C8B C9B C10B -90.90(13) . . . . ?
C7A C8A C9A C10A -24.3(2) . . . . ?
Co1A C8A C9A C10A 93.62(13) . . . . ?
Co2A C8A C9A C10A -145.58(11) . . . . ?
C7C C8C C9C C10C -34.3(2) . . . . ?
Co2C C8C C9C C10C -155.88(10) . . . . ?
Co1C C8C C9C C10C 82.26(14) . . . . ?
C8C C9C C10C C11C 74.74(13) . . . . ?
C8B C9B C10B C11B -73.62(13) . . . . ?
C8A C9A C10A C11A 74.36(14) . . . . ?
C9B C10B C11B C15B 161.66(11) . . . . ?
C9B C10B C11B C12B 87.83(13) . . . . ?
C9C C10C C11C C12C -85.69(14) . . . . ?
C9C C10C C11C C15C -159.84(10) . . . . ?
C9A C10A C11A C15A -162.11(11) . . . . ?
C9A C10A C11A C12A -88.60(14) . . . . ?
C10A C11A C12A C13A -0.88(18) . . . . ?
C15A C11A C12A C13A 111.05(13) . . . . ?
C10A C11A C12A C15A -111.93(13) . . . . ?
C10B C11B C12B C13B 1.71(17) . . . . ?
C15B C11B C12B C13B -111.01(12) . . . . ?
C10B C11B C12B C15B 112.72(13) . . . . ?
C10C C11C C12C C13C -0.05(18) . . . . ?
C15C C11C C12C C13C 111.71(13) . . . . ?
C10C C11C C12C C15C -111.76(13) . . . . ?
C15B C12B C13B C14B -162.40(10) . . . . ?
C11B C12B C13B C14B -89.87(13) . . . . ?
C15C C12C C13C C14C 161.40(10) . . . . ?
C11C C12C C13C C14C 87.14(14) . . . . ?
C15A C12A C13A C14A 160.42(11) . . . . ?
C11A C12A C13A C14A 87.33(14) . . . . ?
C8A C7A C14A C13A 30.1(2) . . . . ?
Co2A C7A C14A C13A 147.05(9) . . . . ?
Co1A C7A C14A C13A -93.19(13) . . . . ?
C12A C13A C14A C7A -73.20(13) . . . . ?
C8C C7C C14C C13C 33.3(2) . . . . ?
Co2C C7C C14C C13C 157.76(10) . . . . ?
Co1C C7C C14C C13C -82.27(13) . . . . ?
C12C C13C C14C C7C -77.13(13) . . . . ?
C8B C7B C14B C13B -26.3(2) . . . . ?
Co1B C7B C14B C13B 93.02(13) . . . . ?
Co2B C7B C14B C13B -147.64(10) . . . . ?
C12B C13B C14B C7B 73.38(12) . . . . ?
C10A C11A C15A C16A 1.76(18) . . . . ?
C12A C11A C15A C16A -111.02(13) . . . . ?
C10A C11A C15A C12A 112.78(13) . . . . ?
C13A C12A C15A C16A -1.94(18) . . . . ?
C11A C12A C15A C16A 110.99(13) . . . . ?
C13A C12A C15A C11A -112.93(13) . . . . ?
C10B C11B C15B C16B -2.36(18) . . . . ?
C12B C11B C15B C16B 110.14(13) . . . . ?
C10B C11B C15B C12B -112.51(13) . . . . ?
C13B C12B C15B C16B -0.93(18) . . . . ?
C11B C12B C15B C16B -112.89(13) . . . . ?
C13B C12B C15B C11B 111.96(12) . . . . ?
C13C C12C C15C C16C -2.30(17) . . . . ?
C11C C12C C15C C16C 111.76(12) . . . . ?
C13C C12C C15C C11C -114.06(12) . . . . ?
C10C C11C C15C C16C 4.70(17) . . . . ?
C12C C11C C15C C16C -109.51(12) . . . . ?
C10C C11C C15C C12C 114.21(12) . . . . ?
C12C C15C C16C O7C 79.89(14) . . . . ?
C11C C15C C16C O7C 151.56(10) . . . . ?
C11B C15B C16B O7B -154.41(11) . . . . ?
C12B C15B C16B O7B -81.68(14) . . . . ?
C11A C15A C16A O7A 167.99(10) . . . . ?
C12A C15A C16A O7A 95.77(13) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O7A H7AA O7C 0.84 1.87 2.7036(16) 175.5 .
O7A' H7A' O7B' 0.84 1.88 2.7217(15) 179.9 1_545
O7B H7BA O7C 0.84 1.87 2.6997(15) 168.4 2_576
O7B' H7B' O7A' 0.84 1.88 2.7217(15) 179.9 1_565
O7C H7CA O7B 0.84 1.94 2.6997(15) 149.0 2_576
O7C' H7C' O7A' 0.84 1.86 2.7036(16) 179.9 .

_refine_diff_density_max         0.539
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.071
_shelxl_version_number           2014-3

_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Bruker Apex2'
_diffrn_measurement_device       'κ-geometry diffractometer'
####################################################################### 
# 
# 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_exo-2
_database_code_depnum_ccdc_archive 'CCDC 1050356'
_audit_update_record             
;
2015-02-18 deposited with the CCDC.
2015-03-12 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H14 Co2 O7'
_chemical_formula_weight         436.13
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'
O O 0.0106 0.0060 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.074(3)
_cell_length_b                   12.983(6)
_cell_length_c                   16.699(5)
_cell_angle_alpha                110.879(17)
_cell_angle_beta                 96.205(8)
_cell_angle_gamma                98.023(9)
_cell_volume                     1793.4(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    110
_cell_measurement_reflns_used    9902
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      28.78
_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.615
_exptl_crystal_F_000             880
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.416
_exptl_crystal_size_mid          0.096
_exptl_crystal_size_min          0.091
_exptl_absorpt_coefficient_mu    1.883
_shelx_estimated_absorpt_T_min   0.508
_shelx_estimated_absorpt_T_max   0.847
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6182
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      110
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker Kappa Axis Apex2'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25939
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.844
_diffrn_reflns_theta_max         28.831
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             9214
_reflns_number_gt                7879
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_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.
;

_computing_data_collection       Apex2
_computing_cell_refinement       SAINT
_computing_data_reduction        SAINT
_computing_structure_solution    SIR92
_computing_structure_refinement  SHELXL-2014
_computing_molecular_graphics    NRCVAX
_computing_publication_material  cif2tables.py
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0338P)²+0.4579P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9214
_refine_ls_number_parameters     451
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0285
_refine_ls_wR_factor_ref         0.0701
_refine_ls_wR_factor_gt          0.0668
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.77587(2) 0.71542(2) 0.62994(2) 0.01948(6) Uani 1 1 d . . . . .
Co2 Co 0.95939(3) 0.78735(2) 0.55537(2) 0.02221(6) Uani 1 1 d . . . . .
C1 C 0.70181(18) 0.57716(15) 0.54555(11) 0.0225(3) Uani 1 1 d . . . . .
O1 O 0.66664(15) 0.48896(11) 0.49509(8) 0.0332(3) Uani 1 1 d . . . . .
C2 C 0.6467(2) 0.80939(18) 0.62837(13) 0.0356(5) Uani 1 1 d . . . . .
O2 O 0.57050(18) 0.87221(15) 0.62968(12) 0.0582(5) Uani 1 1 d . . . . .
C3 C 0.7378(2) 0.68297(18) 0.72185(12) 0.0339(5) Uani 1 1 d . . . . .
O3 O 0.7190(2) 0.65963(16) 0.77997(10) 0.0581(5) Uani 1 1 d . . . . .
C4 C 0.9044(3) 0.91960(18) 0.56171(14) 0.0440(6) Uani 1 1 d . . . . .
O4 O 0.8713(3) 1.00330(15) 0.57002(14) 0.0758(7) Uani 1 1 d . . . . .
C5 C 0.87566(19) 0.68824(16) 0.44709(11) 0.0248(4) Uani 1 1 d . . . . .
O5 O 0.82105(16) 0.62729(12) 0.37912(8) 0.0347(3) Uani 1 1 d . . . . .
C6 C 1.1493(2) 0.8057(2) 0.53580(13) 0.0432(6) Uani 1 1 d . . . . .
O6 O 1.26932(17) 0.8112(2) 0.52092(11) 0.0693(6) Uani 1 1 d . . . . .
O7 O 1.58091(17) 0.92030(12) 0.96869(10) 0.0467(4) Uani 0.5 1 d . . P A 1
H7 H 1.5363 0.9751 0.9821 0.070 Uiso 0.5 1 d R U P A 1
O7' O 1.58091(17) 0.92030(12) 0.96869(10) 0.0467(4) Uani 0.5 1 d . . P A 2
H7' H 1.6740 0.9201 0.9738 0.070 Uiso 0.5 1 d R U P A 2
C7 C 0.99163(17) 0.71058(14) 0.63727(10) 0.0171(3) Uani 1 1 d . . . . .
C8 C 0.97580(17) 0.81531(14) 0.68073(10) 0.0177(3) Uani 1 1 d . . . . .
C9 C 1.03816(18) 0.91750(13) 0.76089(11) 0.0199(3) Uani 1 1 d . . . . .
H9A H 0.9898 0.9108 0.8097 0.024 Uiso 1 1 calc R U . . .
H9B H 1.0128 0.9843 0.7512 0.024 Uiso 1 1 calc R U . . .
C10 C 1.21056(17) 0.93447(13) 0.78608(11) 0.0199(3) Uani 1 1 d . . . . .
H10A H 1.2570 0.9205 0.7331 0.024 Uiso 1 1 calc R U . . .
H10B H 1.2504 1.0134 0.8258 0.024 Uiso 1 1 calc R U . . .
C11 C 1.25454(17) 0.85736(13) 0.82984(10) 0.0170(3) Uani 1 1 d . . . . .
H11 H 1.2146 0.8698 0.8854 0.020 Uiso 1 1 calc R U . . .
C12 C 1.26678(17) 0.73631(13) 0.78205(10) 0.0175(3) Uani 1 1 d . . . . .
H12 H 1.2327 0.6853 0.8121 0.021 Uiso 1 1 calc R U . . .
C13 C 1.24847(18) 0.67831(14) 0.68497(10) 0.0218(3) Uani 1 1 d . . . . .
H13A H 1.3101 0.6190 0.6714 0.026 Uiso 1 1 calc R U . . .
H13B H 1.2877 0.7334 0.6603 0.026 Uiso 1 1 calc R U . . .
C14 C 1.08358(19) 0.62506(14) 0.64108(11) 0.0221(3) Uani 1 1 d . . . . .
H14A H 1.0819 0.5715 0.5812 0.026 Uiso 1 1 calc R U . . .
H14B H 1.0375 0.5823 0.6737 0.026 Uiso 1 1 calc R U . . .
C15 C 1.40650(17) 0.82309(14) 0.83155(10) 0.0189(3) Uani 1 1 d . . . . .
H15 H 1.4725 0.8470 0.7946 0.023 Uiso 1 1 calc R U . . .
C16 C 1.48885(19) 0.81625(15) 0.91162(11) 0.0241(4) Uani 1 1 d . . . . .
H16A H 1.4143 0.7912 0.9432 0.029 Uiso 1 1 calc R U . A 1
H16B H 1.5532 0.7591 0.8942 0.029 Uiso 1 1 calc R U . A 1
Co1A Co 0.42625(2) 0.31311(2) 0.81881(2) 0.01806(6) Uani 1 1 d . . . . .
Co2A Co 0.58951(3) 0.26331(2) 0.70793(2) 0.02141(6) Uani 1 1 d . . . . .
C3A C 0.2581(2) 0.21326(16) 0.75390(13) 0.0300(4) Uani 1 1 d . . . . .
C2A C 0.3989(2) 0.33710(17) 0.92781(13) 0.0301(4) Uani 1 1 d . . . . .
C1A C 0.3998(2) 0.44822(16) 0.81688(13) 0.0318(4) Uani 1 1 d . . . . .
C6A C 0.5569(2) 0.37084(19) 0.66704(13) 0.0348(4) Uani 1 1 d . . . . .
C4A C 0.4772(3) 0.1349(2) 0.62417(13) 0.0438(5) Uani 1 1 d . . . . .
C5A C 0.7753(2) 0.2560(2) 0.68394(13) 0.0385(5) Uani 1 1 d . . . . .
C7A C 0.58063(16) 0.21795(13) 0.80845(10) 0.0157(3) Uani 1 1 d . . . . .
C8A C 0.64653(18) 0.32562(14) 0.83564(10) 0.0189(3) Uani 1 1 d . . . . .
C9A C 0.7790(2) 0.40870(15) 0.89667(12) 0.0282(4) Uani 1 1 d . . . . .
H25A H 0.7511 0.4414 0.9550 0.034 Uiso 1 1 calc R U . . .
H25B H 0.8048 0.4705 0.8760 0.034 Uiso 1 1 calc R U . . .
C10A C 0.91853(19) 0.35513(15) 0.90413(12) 0.0264(4) Uani 1 1 d . . . . .
H26A H 0.9311 0.3072 0.8451 0.032 Uiso 1 1 calc R U . . .
H26B H 1.0093 0.4155 0.9293 0.032 Uiso 1 1 calc R U . . .
C11A C 0.90920(18) 0.28565(15) 0.95895(11) 0.0233(4) Uani 1 1 d . . . . .
H27 H 0.9009 0.3293 1.0206 0.028 Uiso 1 1 calc R U . . .
C12A C 0.83443(18) 0.16255(15) 0.92654(11) 0.0216(3) Uani 1 1 d . . . . .
H28 H 0.7869 0.1417 0.9713 0.026 Uiso 1 1 calc R U . . .
C13A C 0.75476(17) 0.09441(14) 0.83506(11) 0.0201(3) Uani 1 1 d . . . . .
H29A H 0.7554 0.0140 0.8224 0.024 Uiso 1 1 calc R U . . .
H29B H 0.8104 0.1166 0.7941 0.024 Uiso 1 1 calc R U . . .
C14A C 0.59031(17) 0.11023(13) 0.82010(11) 0.0194(3) Uani 1 1 d . . . . .
H30A H 0.5332 0.0468 0.7678 0.023 Uiso 1 1 calc R U . . .
H30B H 0.5427 0.1090 0.8705 0.023 Uiso 1 1 calc R U . . .
C15A C 1.00409(19) 0.19618(15) 0.94943(11) 0.0233(4) Uani 1 1 d . . . . .
H31 H 1.0586 0.1794 0.8987 0.028 Uiso 1 1 calc R U . . .
C16A C 1.0874(2) 0.18954(17) 1.02962(12) 0.0309(4) Uani 1 1 d . . . . .
H32A H 1.1828 0.2457 1.0498 0.037 Uiso 1 1 calc R U . B 1
H32B H 1.0254 0.2088 1.0763 0.037 Uiso 1 1 calc R U . B 1
O3A O 0.15681(17) 0.14767(14) 0.71147(12) 0.0540(5) Uani 1 1 d . . . . .
O2A O 0.38733(19) 0.35665(14) 0.99880(10) 0.0465(4) Uani 1 1 d . . . . .
O1A O 0.3862(2) 0.53364(13) 0.81691(11) 0.0562(5) Uani 1 1 d . . . . .
O6A O 0.53347(19) 0.43702(15) 0.64009(12) 0.0546(5) Uani 1 1 d . . . . .
O5A O 0.4074(3) 0.05499(17) 0.57435(14) 0.0893(8) Uani 1 1 d . . . . .
O4A O 0.89590(18) 0.25670(18) 0.67066(11) 0.0576(5) Uani 1 1 d . . . . .
O7A O 1.12103(18) 0.08081(15) 1.01511(11) 0.0523(4) Uani 0.5 1 d . . P C 1
H7A' H 1.0718 0.0297 0.9694 0.078 Uiso 0.5 1 d R U P C 1
O7A' O 1.12103(18) 0.08081(15) 1.01511(11) 0.0523(4) Uani 0.5 1 d . . P C 2
H7A H 1.2092 0.0693 1.0232 0.078 Uiso 0.5 1 d R U P C 2


_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 C3 1.785(2) . ?
Co1 C2 1.810(2) . ?
Co1 C1 1.8208(19) . ?
Co1 C7 1.9595(16) . ?
Co1 C8 1.9796(17) . ?
Co1 Co2 2.4573(6) . ?
Co2 C6 1.788(2) . ?
Co2 C5 1.8095(19) . ?
Co2 C4 1.825(2) . ?
Co2 C8 1.9778(17) . ?
Co2 C7 1.9788(17) . ?
C1 O1 1.129(2) . ?
C2 O2 1.137(2) . ?
C3 O3 1.137(2) . ?
C4 O4 1.133(3) . ?
C5 O5 1.135(2) . ?
C6 O6 1.141(3) . ?
O7 C16 1.423(2) . ?
O7 H7 0.8401 . ?
O7' C16 1.423(2) . ?
O7' H7' 0.8400 . ?
C7 C8 1.330(2) . ?
C7 C14 1.494(2) . ?
C8 C9 1.494(2) . ?
C9 C10 1.539(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.505(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C15 1.507(2) . ?
C11 C12 1.514(2) . ?
C11 H11 1.0000 . ?
C12 C13 1.503(2) . ?
C12 C15 1.507(2) . ?
C12 H12 1.0000 . ?
C13 C14 1.538(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.497(2) . ?
C15 H15 1.0000 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
Co1A C2A 1.785(2) . ?
Co1A C3A 1.809(2) . ?
Co1A C1A 1.814(2) . ?
Co1A C8A 1.9636(17) . ?
Co1A C7A 1.9753(15) . ?
Co1A Co2A 2.4593(6) . ?
Co2A C5A 1.782(2) . ?
Co2A C6A 1.804(2) . ?
Co2A C4A 1.825(2) . ?
Co2A C8A 1.9711(17) . ?
Co2A C7A 1.9727(16) . ?
C3A O3A 1.132(2) . ?
C2A O2A 1.140(2) . ?
C1A O1A 1.133(2) . ?
C6A O6A 1.137(2) . ?
C4A O5A 1.121(3) . ?
C5A O4A 1.139(2) . ?
C7A C8A 1.332(2) . ?
C7A C14A 1.492(2) . ?
C8A C9A 1.495(2) . ?
C9A C10A 1.542(2) . ?
C9A H25A 0.9900 . ?
C9A H25B 0.9900 . ?
C10A C11A 1.498(3) . ?
C10A H26A 0.9900 . ?
C10A H26B 0.9900 . ?
C11A C15A 1.514(2) . ?
C11A C12A 1.519(3) . ?
C11A H27 1.0000 . ?
C12A C13A 1.503(2) . ?
C12A C15A 1.508(2) . ?
C12A H28 1.0000 . ?
C13A C14A 1.540(2) . ?
C13A H29A 0.9900 . ?
C13A H29B 0.9900 . ?
C14A H30A 0.9900 . ?
C14A H30B 0.9900 . ?
C15A C16A 1.501(2) . ?
C15A H31 1.0000 . ?
C16A O7A' 1.427(2) . ?
C16A O7A 1.427(2) . ?
C16A H32A 0.9900 . ?
C16A H32B 0.9900 . ?
O7A H7A' 0.8400 . ?
O7A' H7A 0.8400 . ?

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
C3 Co1 C2 101.37(10) . . ?
C3 Co1 C1 98.33(9) . . ?
C2 Co1 C1 110.03(9) . . ?
C3 Co1 C7 100.17(8) . . ?
C2 Co1 C7 140.83(9) . . ?
C1 Co1 C7 98.66(7) . . ?
C3 Co1 C8 99.01(8) . . ?
C2 Co1 C8 104.65(9) . . ?
C1 Co1 C8 136.96(7) . . ?
C7 Co1 C8 39.47(7) . . ?
C3 Co1 Co2 148.93(6) . . ?
C2 Co1 Co2 96.62(8) . . ?
C1 Co1 Co2 99.01(6) . . ?
C7 Co1 Co2 51.75(5) . . ?
C8 Co1 Co2 51.58(5) . . ?
C6 Co2 C5 96.69(9) . . ?
C6 Co2 C4 102.89(12) . . ?
C5 Co2 C4 105.15(9) . . ?
C6 Co2 C8 105.65(8) . . ?
C5 Co2 C8 144.27(8) . . ?
C4 Co2 C8 96.74(9) . . ?
C6 Co2 C7 96.94(8) . . ?
C5 Co2 C7 111.48(8) . . ?
C4 Co2 C7 135.63(9) . . ?
C8 Co2 C7 39.30(7) . . ?
C6 Co2 Co1 147.98(7) . . ?
C5 Co2 Co1 95.63(6) . . ?
C4 Co2 Co1 102.19(9) . . ?
C8 Co2 Co1 51.65(5) . . ?
C7 Co2 Co1 51.05(5) . . ?
O1 C1 Co1 174.33(16) . . ?
O2 C2 Co1 177.00(19) . . ?
O3 C3 Co1 176.8(2) . . ?
O4 C4 Co2 176.6(2) . . ?
O5 C5 Co2 178.66(17) . . ?
O6 C6 Co2 176.2(3) . . ?
C16 O7 H7 114.8 . . ?
C16 O7' H7' 114.1 . . ?
C8 C7 C14 142.30(14) . . ?
C8 C7 Co1 71.08(9) . . ?
C14 C7 Co1 134.38(13) . . ?
C8 C7 Co2 70.31(10) . . ?
C14 C7 Co2 133.59(12) . . ?
Co1 C7 Co2 77.21(6) . . ?
C7 C8 C9 143.50(14) . . ?
C7 C8 Co2 70.39(10) . . ?
C9 C8 Co2 132.56(12) . . ?
C7 C8 Co1 69.45(10) . . ?
C9 C8 Co1 135.50(12) . . ?
Co2 C8 Co1 76.77(6) . . ?
C8 C9 C10 112.43(13) . . ?
C8 C9 H9A 109.1 . . ?
C10 C9 H9A 109.1 . . ?
C8 C9 H9B 109.1 . . ?
C10 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
C11 C10 C9 112.02(14) . . ?
C11 C10 H10A 109.2 . . ?
C9 C10 H10A 109.2 . . ?
C11 C10 H10B 109.2 . . ?
C9 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C10 C11 C15 123.43(14) . . ?
C10 C11 C12 124.40(14) . . ?
C15 C11 C12 59.83(10) . . ?
C10 C11 H11 113.1 . . ?
C15 C11 H11 113.1 . . ?
C12 C11 H11 113.1 . . ?
C13 C12 C15 119.92(15) . . ?
C13 C12 C11 125.35(14) . . ?
C15 C12 C11 59.85(10) . . ?
C13 C12 H12 113.7 . . ?
C15 C12 H12 113.7 . . ?
C11 C12 H12 113.7 . . ?
C12 C13 C14 113.25(14) . . ?
C12 C13 H13A 108.9 . . ?
C14 C13 H13A 108.9 . . ?
C12 C13 H13B 108.9 . . ?
C14 C13 H13B 108.9 . . ?
H13A C13 H13B 107.7 . . ?
C7 C14 C13 112.42(14) . . ?
C7 C14 H14A 109.1 . . ?
C13 C14 H14A 109.1 . . ?
C7 C14 H14B 109.1 . . ?
C13 C14 H14B 109.1 . . ?
H14A C14 H14B 107.9 . . ?
C16 C15 C12 118.89(15) . . ?
C16 C15 C11 121.61(14) . . ?
C12 C15 C11 60.32(10) . . ?
C16 C15 H15 115.0 . . ?
C12 C15 H15 115.0 . . ?
C11 C15 H15 115.0 . . ?
O7' C16 C15 113.12(15) . . ?
O7 C16 C15 113.12(15) . . ?
O7 C16 H16A 109.0 . . ?
C15 C16 H16A 109.0 . . ?
O7 C16 H16B 109.0 . . ?
C15 C16 H16B 109.0 . . ?
H16A C16 H16B 107.8 . . ?
C2A Co1A C3A 103.32(10) . . ?
C2A Co1A C1A 98.33(9) . . ?
C3A Co1A C1A 106.15(9) . . ?
C2A Co1A C8A 98.83(8) . . ?
C3A Co1A C8A 139.37(8) . . ?
C1A Co1A C8A 103.77(8) . . ?
C2A Co1A C7A 99.98(7) . . ?
C3A Co1A C7A 102.60(8) . . ?
C1A Co1A C7A 141.07(8) . . ?
C8A Co1A C7A 39.52(7) . . ?
C2A Co1A Co2A 148.48(6) . . ?
C3A Co1A Co2A 96.74(7) . . ?
C1A Co1A Co2A 99.12(7) . . ?
C8A Co1A Co2A 51.45(5) . . ?
C7A Co1A Co2A 51.42(5) . . ?
C5A Co2A C6A 97.17(10) . . ?
C5A Co2A C4A 102.36(11) . . ?
C6A Co2A C4A 103.55(11) . . ?
C5A Co2A C8A 96.88(8) . . ?
C6A Co2A C8A 111.53(9) . . ?
C4A Co2A C8A 137.22(9) . . ?
C5A Co2A C7A 105.72(8) . . ?
C6A Co2A C7A 144.14(8) . . ?
C4A Co2A C7A 98.14(9) . . ?
C8A Co2A C7A 39.47(7) . . ?
C5A Co2A Co1A 148.06(7) . . ?
C6A Co2A Co1A 95.46(7) . . ?
C4A Co2A Co1A 102.98(8) . . ?
C8A Co2A Co1A 51.18(5) . . ?
C7A Co2A Co1A 51.52(5) . . ?
O3A C3A Co1A 176.97(19) . . ?
O2A C2A Co1A 176.6(2) . . ?
O1A C1A Co1A 178.47(19) . . ?
O6A C6A Co2A 178.4(2) . . ?
O5A C4A Co2A 178.2(3) . . ?
O4A C5A Co2A 176.8(2) . . ?
C8A C7A C14A 143.74(14) . . ?
C8A C7A Co2A 70.20(10) . . ?
C14A C7A Co2A 132.75(11) . . ?
C8A C7A Co1A 69.77(10) . . ?
C14A C7A Co1A 134.82(11) . . ?
Co2A C7A Co1A 77.06(6) . . ?
C7A C8A C9A 141.46(15) . . ?
C7A C8A Co1A 70.71(9) . . ?
C9A C8A Co1A 135.99(12) . . ?
C7A C8A Co2A 70.33(10) . . ?
C9A C8A Co2A 132.90(13) . . ?
Co1A C8A Co2A 77.37(6) . . ?
C8A C9A C10A 112.27(14) . . ?
C8A C9A H25A 109.2 . . ?
C10A C9A H25A 109.2 . . ?
C8A C9A H25B 109.2 . . ?
C10A C9A H25B 109.2 . . ?
H25A C9A H25B 107.9 . . ?
C11A C10A C9A 113.71(16) . . ?
C11A C10A H26A 108.8 . . ?
C9A C10A H26A 108.8 . . ?
C11A C10A H26B 108.8 . . ?
C9A C10A H26B 108.8 . . ?
H26A C10A H26B 107.7 . . ?
C10A C11A C15A 120.92(15) . . ?
C10A C11A C12A 125.12(14) . . ?
C15A C11A C12A 59.60(11) . . ?
C10A C11A H27 113.6 . . ?
C15A C11A H27 113.6 . . ?
C12A C11A H27 113.6 . . ?
C13A C12A C15A 122.18(14) . . ?
C13A C12A C11A 124.43(15) . . ?
C15A C12A C11A 60.03(11) . . ?
C13A C12A H28 113.4 . . ?
C15A C12A H28 113.4 . . ?
C11A C12A H28 113.4 . . ?
C12A C13A C14A 112.40(13) . . ?
C12A C13A H29A 109.1 . . ?
C14A C13A H29A 109.1 . . ?
C12A C13A H29B 109.1 . . ?
C14A C13A H29B 109.1 . . ?
H29A C13A H29B 107.9 . . ?
C7A C14A C13A 112.13(13) . . ?
C7A C14A H30A 109.2 . . ?
C13A C14A H30A 109.2 . . ?
C7A C14A H30B 109.2 . . ?
C13A C14A H30B 109.2 . . ?
H30A C14A H30B 107.9 . . ?
C16A C15A C12A 120.81(16) . . ?
C16A C15A C11A 119.19(15) . . ?
C12A C15A C11A 60.38(11) . . ?
C16A C15A H31 115.2 . . ?
C12A C15A H31 115.2 . . ?
C11A C15A H31 115.2 . . ?
O7A' C16A C15A 112.57(16) . . ?
O7A C16A C15A 112.57(16) . . ?
O7A C16A H32A 109.1 . . ?
C15A C16A H32A 109.1 . . ?
O7A C16A H32B 109.1 . . ?
C15A C16A H32B 109.1 . . ?
H32A C16A H32B 107.8 . . ?
C16A O7A H7A' 114.5 . . ?
C16A O7A' H7A 123.3 . . ?

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
C14 C7 C8 C9 0.8(4) . . . . ?
Co1 C7 C8 C9 140.7(3) . . . . ?
Co2 C7 C8 C9 -136.5(3) . . . . ?
C14 C7 C8 Co2 137.3(3) . . . . ?
Co1 C7 C8 Co2 -82.77(4) . . . . ?
C14 C7 C8 Co1 -140.0(3) . . . . ?
Co2 C7 C8 Co1 82.77(4) . . . . ?
C7 C8 C9 C10 35.4(3) . . . . ?
Co2 C8 C9 C10 -82.92(17) . . . . ?
Co1 C8 C9 C10 157.66(13) . . . . ?
C8 C9 C10 C11 -77.68(18) . . . . ?
C9 C10 C11 C15 156.33(14) . . . . ?
C9 C10 C11 C12 82.46(19) . . . . ?
C10 C11 C12 C13 4.8(2) . . . . ?
C15 C11 C12 C13 -107.17(18) . . . . ?
C10 C11 C12 C15 111.98(18) . . . . ?
C15 C12 C13 C14 -160.06(14) . . . . ?
C11 C12 C13 C14 -87.7(2) . . . . ?
C8 C7 C14 C13 -33.5(3) . . . . ?
Co1 C7 C14 C13 -155.11(13) . . . . ?
Co2 C7 C14 C13 84.63(18) . . . . ?
C12 C13 C14 C7 74.26(19) . . . . ?
C13 C12 C15 C16 -132.04(16) . . . . ?
C11 C12 C15 C16 112.00(16) . . . . ?
C13 C12 C15 C11 115.96(16) . . . . ?
C10 C11 C15 C16 138.87(17) . . . . ?
C12 C11 C15 C16 -107.59(18) . . . . ?
C10 C11 C15 C12 -113.54(17) . . . . ?
C12 C15 C16 O7' -158.37(14) . . . . ?
C11 C15 C16 O7' -87.3(2) . . . . ?
C12 C15 C16 O7 -158.37(14) . . . . ?
C11 C15 C16 O7 -87.3(2) . . . . ?
C14A C7A C8A C9A 1.5(4) . . . . ?
Co2A C7A C8A C9A -135.4(3) . . . . ?
Co1A C7A C8A C9A 141.6(3) . . . . ?
C14A C7A C8A Co1A -140.1(2) . . . . ?
Co2A C7A C8A Co1A 83.05(4) . . . . ?
C14A C7A C8A Co2A 136.8(2) . . . . ?
Co1A C7A C8A Co2A -83.05(4) . . . . ?
C7A C8A C9A C10A 34.5(3) . . . . ?
Co1A C8A C9A C10A 156.91(15) . . . . ?
Co2A C8A C9A C10A -80.9(2) . . . . ?
C8A C9A C10A C11A -76.2(2) . . . . ?
C9A C10A C11A C15A 158.62(15) . . . . ?
C9A C10A C11A C12A 86.1(2) . . . . ?
C10A C11A C12A C13A -2.1(2) . . . . ?
C15A C11A C12A C13A -110.50(17) . . . . ?
C10A C11A C12A C15A 108.40(18) . . . . ?
C15A C12A C13A C14A -156.83(15) . . . . ?
C11A C12A C13A C14A -83.35(19) . . . . ?
C8A C7A C14A C13A -37.9(3) . . . . ?
Co2A C7A C14A C13A 80.81(18) . . . . ?
Co1A C7A C14A C13A -159.93(13) . . . . ?
C12A C13A C14A C7A 78.05(18) . . . . ?
C13A C12A C15A C16A -137.60(18) . . . . ?
C11A C12A C15A C16A 108.30(18) . . . . ?
C13A C12A C15A C11A 114.09(18) . . . . ?
C10A C11A C15A C16A 133.86(18) . . . . ?
C12A C11A C15A C16A -110.93(19) . . . . ?
C10A C11A C15A C12A -115.21(17) . . . . ?
C12A C15A C16A O7A' 86.0(2) . . . . ?
C11A C15A C16A O7A' 156.95(17) . . . . ?
C12A C15A C16A O7A 86.0(2) . . . . ?
C11A C15A C16A O7A 156.95(17) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O7 H7 O7 0.84 1.86 2.678(3) 165.2 2_877

_refine_diff_density_max         0.562
_refine_diff_density_min         -0.530
_refine_diff_density_rms         0.076
_shelxl_version_number           2014/6

_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Bruker Apex2'
_diffrn_measurement_device       'κ-geometry diffractometer'
####################################################################### 
# 
# 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_exo-4
_database_code_depnum_ccdc_archive 'CCDC 1050357'
_audit_update_record             
;
2015-02-18 deposited with the CCDC.
2015-03-12 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H17 Co2 N O11'
_chemical_formula_weight         601.23
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'
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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'
_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.
;

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                   39.343(20)
_cell_length_b                   8.101(4)
_cell_length_c                   16.720(6)
_cell_angle_alpha                90
_cell_angle_beta                 110.966(13)
_cell_angle_gamma                90
_cell_volume                     4976(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    110
_cell_measurement_reflns_used    9897
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      24.63
_exptl_crystal_description       Needle
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.605
_exptl_crystal_F_000             2432
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.113
_exptl_crystal_size_mid          0.038
_exptl_crystal_size_min          0.037
_exptl_absorpt_coefficient_mu    1.394
_shelx_estimated_absorpt_T_min   0.858
_shelx_estimated_absorpt_T_max   0.950
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6625
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      110
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker Kappa Axis Apex2'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            61507
_diffrn_reflns_av_unetI/netI     0.0492
_diffrn_reflns_av_R_equivalents  0.0836
_diffrn_reflns_limit_h_min       -47
_diffrn_reflns_limit_h_max       47
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.577
_diffrn_reflns_theta_max         25.337
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4529
_reflns_number_gt                3297
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_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.
;

_computing_data_collection       Apex2
_computing_cell_refinement       SAINT
_computing_data_reduction        SAINT
_computing_structure_solution    SHELXT
_computing_structure_refinement  SHELXL-2014
_computing_molecular_graphics    NRCVAX
_computing_publication_material  cif2tables.py
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0246P)²+8.6377P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4529
_refine_ls_number_parameters     353
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0360
_refine_ls_wR_factor_ref         0.0724
_refine_ls_wR_factor_gt          0.0636
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_refine_ls_shift/su_max          0.002
_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_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 0.69969(2) 0.87097(5) 0.86996(2) 0.02451(12) Uani 1 1 d . . . . .
Co2 Co 0.66082(2) 1.07421(5) 0.76582(2) 0.02501(12) Uani 1 1 d . U . . .
C1 C 0.73946(9) 1.0012(5) 0.90454(18) 0.0433(9) Uani 1 1 d . . . . .
O1 O 0.76436(7) 1.0849(4) 0.92622(15) 0.0774(10) Uani 1 1 d . . . . .
C2 C 0.68319(8) 0.8674(4) 0.95879(18) 0.0261(7) Uani 1 1 d . . . . .
O2 O 0.67303(6) 0.8561(3) 1.01418(13) 0.0371(5) Uani 1 1 d . . . . .
C3 C 0.72077(9) 0.6727(5) 0.88127(18) 0.0407(9) Uani 1 1 d . . . . .
O3 O 0.73347(8) 0.5451(4) 0.88392(15) 0.0669(9) Uani 1 1 d . . . . .
C4 C 0.69322(9) 1.2085(4) 0.7436(2) 0.0399(9) Uani 1 1 d . . . . .
O4 O 0.71309(7) 1.2878(3) 0.72373(17) 0.0634(8) Uani 1 1 d . . . . .
C5 C 0.6494(5) 1.202(2) 0.8390(8) 0.034(3) Uani 0.55(4) 1 d . U P A 1
O5 O 0.6433(7) 1.279(3) 0.8890(4) 0.065(6) Uani 0.55(4) 1 d . U P A 1
C5' C 0.6409(5) 1.144(3) 0.8457(10) 0.030(4) Uani 0.45(4) 1 d . U P A 2
O5' O 0.6279(4) 1.190(4) 0.8916(5) 0.057(6) Uani 0.45(4) 1 d . U P A 2
C6 C 0.62167(8) 1.1114(3) 0.67249(18) 0.0235(7) Uani 1 1 d . . . . .
O6 O 0.59648(6) 1.1340(2) 0.61289(13) 0.0333(5) Uani 1 1 d . . . . .
C7 C 0.65403(7) 0.8327(4) 0.77351(16) 0.0216(6) Uani 1 1 d . . . . .
C8 C 0.68048(7) 0.8633(3) 0.74343(16) 0.0205(6) Uani 1 1 d . . . . .
C9 C 0.69542(7) 0.8122(4) 0.67693(15) 0.0205(6) Uani 1 1 d . . . . .
H9A H 0.7104 0.7116 0.6964 0.025 Uiso 1 1 calc R U . . .
H9B H 0.7114 0.9008 0.6694 0.025 Uiso 1 1 calc R U . . .
C10 C 0.66496(7) 0.7774(3) 0.59073(15) 0.0188(6) Uani 1 1 d . . . . .
H10A H 0.6462 0.8648 0.5795 0.023 Uiso 1 1 calc R U . . .
H10B H 0.6752 0.7826 0.5447 0.023 Uiso 1 1 calc R U . . .
C11 C 0.64720(7) 0.6126(3) 0.58754(15) 0.0184(6) Uani 1 1 d . . . . .
H11 H 0.6641 0.5175 0.5935 0.022 Uiso 1 1 calc R U . . .
C12 C 0.61689(7) 0.5761(3) 0.62138(16) 0.0184(6) Uani 1 1 d . . . . .
H12 H 0.6179 0.4624 0.6454 0.022 Uiso 1 1 calc R U . . .
C13 C 0.59975(7) 0.7016(3) 0.66170(16) 0.0207(6) Uani 1 1 d . . . . .
H13A H 0.5747 0.6654 0.6538 0.025 Uiso 1 1 calc R U . . .
H13B H 0.5980 0.8083 0.6316 0.025 Uiso 1 1 calc R U . . .
C14 C 0.62100(7) 0.7277(4) 0.75772(16) 0.0242(7) Uani 1 1 d . . . . .
H14A H 0.6049 0.7808 0.7840 0.029 Uiso 1 1 calc R U . . .
H14B H 0.6285 0.6191 0.7856 0.029 Uiso 1 1 calc R U . . .
C15 C 0.60893(7) 0.5795(3) 0.52597(16) 0.0184(6) Uani 1 1 d . . . . .
H15 H 0.5954 0.6790 0.4954 0.022 Uiso 1 1 calc R U . . .
C16 C 0.60117(7) 0.4250(3) 0.47503(17) 0.0220(6) Uani 1 1 d . . . . .
H16A H 0.6032 0.4442 0.4184 0.026 Uiso 1 1 calc R U . . .
H16B H 0.6188 0.3381 0.5051 0.026 Uiso 1 1 calc R U . . .
C17 C 0.55477(8) 0.2287(3) 0.42599(16) 0.0212(7) Uani 1 1 d . . . . .
C18 C 0.50666(7) 0.0400(3) 0.39065(17) 0.0198(6) Uani 1 1 d . . . . .
C19 C 0.52142(8) -0.1058(3) 0.43092(17) 0.0248(7) Uani 1 1 d . . . . .
H19 H 0.5419 -0.1044 0.4828 0.030 Uiso 1 1 calc R U . . .
C20 C 0.50595(8) -0.2541(4) 0.39459(17) 0.0242(7) Uani 1 1 d . . . . .
H20 H 0.5157 -0.3564 0.4205 0.029 Uiso 1 1 calc R U . . .
C21 C 0.47590(7) -0.2491(3) 0.31961(17) 0.0208(6) Uani 1 1 d . . . . .
C22 C 0.46084(7) -0.1039(3) 0.27960(17) 0.0223(7) Uani 1 1 d . . . . .
H22 H 0.4401 -0.1054 0.2283 0.027 Uiso 1 1 calc R U . . .
C23 C 0.47663(7) 0.0445(3) 0.31565(17) 0.0215(6) Uani 1 1 d . . . . .
H23 H 0.4670 0.1467 0.2894 0.026 Uiso 1 1 calc R U . . .
O7 O 0.56410(5) 0.3736(2) 0.46442(11) 0.0212(4) Uani 1 1 d . . . . .
O8 O 0.57185(5) 0.1441(2) 0.39564(12) 0.0289(5) Uani 1 1 d . . . . .
O9 O 0.52119(5) 0.1914(2) 0.42738(11) 0.0241(5) Uani 1 1 d . . . . .
O10 O 0.47660(6) -0.5330(3) 0.30615(15) 0.0428(6) Uani 1 1 d . . . . .
O11 O 0.42962(6) -0.4022(3) 0.22400(15) 0.0533(7) Uani 1 1 d . . . . .
N1 N 0.45974(7) -0.4060(3) 0.28044(16) 0.0299(6) 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 C3 1.786(4) . ?
Co1 C1 1.802(4) . ?
Co1 C2 1.822(3) . ?
Co1 C7 1.962(3) . ?
Co1 C8 1.977(3) . ?
Co1 Co2 2.4851(9) . ?
Co2 C5 1.778(12) . ?
Co2 C6 1.783(3) . ?
Co2 C4 1.812(4) . ?
Co2 C5' 1.863(16) . ?
Co2 C8 1.966(3) . ?
Co2 C7 1.985(3) . ?
C1 O1 1.139(4) . ?
C2 O2 1.136(3) . ?
C3 O3 1.142(4) . ?
C4 O4 1.149(4) . ?
C5 O5 1.137(10) . ?
C5' O5' 1.124(13) . ?
C6 O6 1.141(3) . ?
C7 C8 1.331(4) . ?
C7 C14 1.496(4) . ?
C8 C9 1.490(4) . ?
C9 C10 1.535(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.499(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C15 1.513(4) . ?
C11 C12 1.521(4) . ?
C11 H11 1.0000 . ?
C12 C13 1.506(4) . ?
C12 C15 1.512(4) . ?
C12 H12 1.0000 . ?
C13 C14 1.537(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.483(4) . ?
C15 H15 1.0000 . ?
C16 O7 1.465(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 O8 1.193(3) . ?
C17 O7 1.325(3) . ?
C17 O9 1.363(3) . ?
C18 C19 1.380(4) . ?
C18 C23 1.382(4) . ?
C18 O9 1.399(3) . ?
C19 C20 1.385(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.382(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.378(4) . ?
C21 N1 1.466(4) . ?
C22 C23 1.388(4) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
O10 N1 1.217(3) . ?
O11 N1 1.223(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
C3 Co1 C1 100.10(17) . . ?
C3 Co1 C2 100.78(14) . . ?
C1 Co1 C2 105.64(13) . . ?
C3 Co1 C7 101.47(14) . . ?
C1 Co1 C7 142.23(13) . . ?
C2 Co1 C7 100.31(12) . . ?
C3 Co1 C8 94.03(12) . . ?
C1 Co1 C8 108.50(12) . . ?
C2 Co1 C8 139.54(12) . . ?
C7 Co1 C8 39.50(11) . . ?
C3 Co1 Co2 144.67(9) . . ?
C1 Co1 Co2 94.77(12) . . ?
C2 Co1 Co2 105.79(10) . . ?
C7 Co1 Co2 51.38(9) . . ?
C8 Co1 Co2 50.73(8) . . ?
C5 Co2 C6 98.8(5) . . ?
C5 Co2 C4 99.3(7) . . ?
C6 Co2 C4 99.80(14) . . ?
C6 Co2 C5' 97.1(5) . . ?
C4 Co2 C5' 118.1(8) . . ?
C5 Co2 C8 148.2(5) . . ?
C6 Co2 C8 104.81(12) . . ?
C4 Co2 C8 97.41(14) . . ?
C5' Co2 C8 134.1(8) . . ?
C5 Co2 C7 117.1(7) . . ?
C6 Co2 C7 97.41(12) . . ?
C4 Co2 C7 136.51(13) . . ?
C5' Co2 C7 98.8(8) . . ?
C8 Co2 C7 39.37(11) . . ?
C5 Co2 Co1 98.4(5) . . ?
C6 Co2 Co1 147.95(9) . . ?
C4 Co2 Co1 103.85(11) . . ?
C5' Co2 Co1 90.6(6) . . ?
C8 Co2 Co1 51.11(8) . . ?
C7 Co2 Co1 50.58(8) . . ?
O1 C1 Co1 179.3(4) . . ?
O2 C2 Co1 176.3(3) . . ?
O3 C3 Co1 176.4(3) . . ?
O4 C4 Co2 174.9(3) . . ?
O5 C5 Co2 176.7(13) . . ?
O5' C5' Co2 177.5(14) . . ?
O6 C6 Co2 179.4(3) . . ?
C8 C7 C14 141.9(3) . . ?
C8 C7 Co1 70.83(16) . . ?
C14 C7 Co1 135.8(2) . . ?
C8 C7 Co2 69.55(17) . . ?
C14 C7 Co2 132.7(2) . . ?
Co1 C7 Co2 78.04(10) . . ?
C7 C8 C9 143.2(3) . . ?
C7 C8 Co2 71.07(17) . . ?
C9 C8 Co2 132.1(2) . . ?
C7 C8 Co1 69.67(16) . . ?
C9 C8 Co1 134.88(19) . . ?
Co2 C8 Co1 78.15(10) . . ?
C8 C9 C10 111.6(2) . . ?
C8 C9 H9A 109.3 . . ?
C10 C9 H9A 109.3 . . ?
C8 C9 H9B 109.3 . . ?
C10 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
C11 C10 C9 113.2(2) . . ?
C11 C10 H10A 108.9 . . ?
C9 C10 H10A 108.9 . . ?
C11 C10 H10B 108.9 . . ?
C9 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
C10 C11 C15 121.3(2) . . ?
C10 C11 C12 125.3(2) . . ?
C15 C11 C12 59.79(17) . . ?
C10 C11 H11 113.4 . . ?
C15 C11 H11 113.4 . . ?
C12 C11 H11 113.4 . . ?
C13 C12 C15 120.2(2) . . ?
C13 C12 C11 124.9(2) . . ?
C15 C12 C11 59.86(16) . . ?
C13 C12 H12 113.8 . . ?
C15 C12 H12 113.8 . . ?
C11 C12 H12 113.8 . . ?
C12 C13 C14 113.4(2) . . ?
C12 C13 H13A 108.9 . . ?
C14 C13 H13A 108.9 . . ?
C12 C13 H13B 108.9 . . ?
C14 C13 H13B 108.9 . . ?
H13A C13 H13B 107.7 . . ?
C7 C14 C13 112.1(2) . . ?
C7 C14 H14A 109.2 . . ?
C13 C14 H14A 109.2 . . ?
C7 C14 H14B 109.2 . . ?
C13 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
C16 C15 C12 120.9(2) . . ?
C16 C15 C11 119.4(2) . . ?
C12 C15 C11 60.35(17) . . ?
C16 C15 H15 115.1 . . ?
C12 C15 H15 115.1 . . ?
C11 C15 H15 115.1 . . ?
O7 C16 C15 107.5(2) . . ?
O7 C16 H16A 110.2 . . ?
C15 C16 H16A 110.2 . . ?
O7 C16 H16B 110.2 . . ?
C15 C16 H16B 110.2 . . ?
H16A C16 H16B 108.5 . . ?
O8 C17 O7 127.9(3) . . ?
O8 C17 O9 125.3(3) . . ?
O7 C17 O9 106.8(2) . . ?
C19 C18 C23 122.6(3) . . ?
C19 C18 O9 120.1(2) . . ?
C23 C18 O9 117.2(2) . . ?
C18 C19 C20 119.1(3) . . ?
C18 C19 H19 120.5 . . ?
C20 C19 H19 120.5 . . ?
C21 C20 C19 118.1(3) . . ?
C21 C20 H20 120.9 . . ?
C19 C20 H20 120.9 . . ?
C22 C21 C20 123.0(3) . . ?
C22 C21 N1 118.7(2) . . ?
C20 C21 N1 118.3(2) . . ?
C21 C22 C23 118.7(2) . . ?
C21 C22 H22 120.6 . . ?
C23 C22 H22 120.6 . . ?
C18 C23 C22 118.4(3) . . ?
C18 C23 H23 120.8 . . ?
C22 C23 H23 120.8 . . ?
C17 O7 C16 113.7(2) . . ?
C17 O9 C18 115.6(2) . . ?
O10 N1 O11 123.3(3) . . ?
O10 N1 C21 118.7(2) . . ?
O11 N1 C21 117.9(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
C14 C7 C8 C9 -2.3(7) . . . . ?
Co1 C7 C8 C9 139.5(4) . . . . ?
Co2 C7 C8 C9 -136.5(4) . . . . ?
C14 C7 C8 Co2 134.1(4) . . . . ?
Co1 C7 C8 Co2 -84.00(8) . . . . ?
C14 C7 C8 Co1 -141.9(4) . . . . ?
Co2 C7 C8 Co1 84.00(8) . . . . ?
C7 C8 C9 C10 40.0(5) . . . . ?
Co2 C8 C9 C10 -78.6(3) . . . . ?
Co1 C8 C9 C10 160.8(2) . . . . ?
C8 C9 C10 C11 -78.2(3) . . . . ?
C9 C10 C11 C15 156.3(2) . . . . ?
C9 C10 C11 C12 83.2(3) . . . . ?
C10 C11 C12 C13 1.2(4) . . . . ?
C15 C11 C12 C13 -107.7(3) . . . . ?
C10 C11 C12 C15 108.9(3) . . . . ?
C15 C12 C13 C14 -157.0(2) . . . . ?
C11 C12 C13 C14 -84.6(3) . . . . ?
C8 C7 C14 C13 -36.7(5) . . . . ?
Co1 C7 C14 C13 -159.9(2) . . . . ?
Co2 C7 C14 C13 77.2(3) . . . . ?
C12 C13 C14 C7 77.3(3) . . . . ?
C13 C12 C15 C16 -136.2(3) . . . . ?
C11 C12 C15 C16 108.5(3) . . . . ?
C13 C12 C15 C11 115.3(3) . . . . ?
C10 C11 C15 C16 133.7(3) . . . . ?
C12 C11 C15 C16 -110.9(3) . . . . ?
C10 C11 C15 C12 -115.3(3) . . . . ?
C12 C15 C16 O7 75.1(3) . . . . ?
C11 C15 C16 O7 146.1(2) . . . . ?
C23 C18 C19 C20 0.8(4) . . . . ?
O9 C18 C19 C20 178.2(2) . . . . ?
C18 C19 C20 C21 -0.8(4) . . . . ?
C19 C20 C21 C22 0.2(4) . . . . ?
C19 C20 C21 N1 179.3(2) . . . . ?
C20 C21 C22 C23 0.5(4) . . . . ?
N1 C21 C22 C23 -178.6(2) . . . . ?
C19 C18 C23 C22 -0.1(4) . . . . ?
O9 C18 C23 C22 -177.6(2) . . . . ?
C21 C22 C23 C18 -0.5(4) . . . . ?
O8 C17 O7 C16 -4.9(4) . . . . ?
O9 C17 O7 C16 174.90(19) . . . . ?
C15 C16 O7 C17 -174.6(2) . . . . ?
O8 C17 O9 C18 0.8(4) . . . . ?
O7 C17 O9 C18 -179.0(2) . . . . ?
C19 C18 O9 C17 70.5(3) . . . . ?
C23 C18 O9 C17 -112.0(3) . . . . ?
C22 C21 N1 O10 166.6(3) . . . . ?
C20 C21 N1 O10 -12.5(4) . . . . ?
C22 C21 N1 O11 -14.3(4) . . . . ?
C20 C21 N1 O11 166.6(3) . . . . ?

_refine_diff_density_max         0.354
_refine_diff_density_min         -0.445
_refine_diff_density_rms         0.070
_shelxl_version_number           2014/6

_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Bruker Apex2'
_diffrn_measurement_device       'κ-geometry diffractometer'
