# Electronic Supplementary Material (ESI) for ChemComm.
# 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_1M
_database_code_depnum_ccdc_archive 'CCDC 1469413'
_audit_update_record             
;
2016-03-18 deposited with the CCDC.
2016-04-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        '(M)-Co(SO4)(1,3-bbix)(H2O)3 '
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H24 Co N4 O7 S'
_chemical_formula_sum            'C22 H24 Co N4 O7 S'
_chemical_formula_weight         547.44

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'
S S 0.1246 0.1234 '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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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+1/2, -z'

_cell_length_a                   11.479(4)
_cell_length_b                   8.356(3)
_cell_length_c                   12.079(4)
_cell_angle_alpha                90
_cell_angle_beta                 104.039(5)
_cell_angle_gamma                90
_cell_volume                     1124.0(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    2649
_cell_measurement_theta_min      2.696
_cell_measurement_theta_max      27.498

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.618
_exptl_crystal_F_000             566
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.910
_shelx_estimated_absorpt_T_min   0.839
_shelx_estimated_absorpt_T_max   0.956
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.897
_exptl_absorpt_correction_T_max  0.956
_exptl_absorpt_process_details   'SADABS(Bruker, 2000)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX DUO'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9857
_diffrn_reflns_av_unetI/netI     0.1039
_diffrn_reflns_av_R_equivalents  0.0673
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.829
_diffrn_reflns_theta_max         27.685
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             4181
_reflns_number_gt                3619
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.877
_reflns_Friedel_fraction_max     0.983
_reflns_Friedel_fraction_full    0.996

_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       'SMART (Bruker, 2000)'
_computing_cell_refinement       SMART
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_structure_solution    'SHELXTL (Bruker, 2000)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1304P)²+9.9313P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.05(4)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         4181
_refine_ls_number_parameters     317
_refine_ls_number_restraints     16
_refine_ls_R_factor_all          0.1110
_refine_ls_R_factor_gt           0.0976
_refine_ls_wR_factor_ref         0.2384
_refine_ls_wR_factor_gt          0.2295
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.001
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001

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 0.14837(8) 0.51734(13) 0.35107(7) 0.01154(19) Uani 1 1 d . . . . .
S1 S 0.03766(16) 0.8762(2) 0.37469(15) 0.0141(4) Uani 1 1 d . . . . .
C1 C 0.5385(8) 1.4207(11) -0.2897(8) 0.025(2) Uani 1 1 d . . . . .
H1 H 0.5553 1.5309 -0.2743 0.030 Uiso 1 1 calc R U . . .
C2 C 0.4270(7) 1.3620(12) -0.2843(7) 0.024(2) Uani 1 1 d . . . . .
H2 H 0.3709 1.4327 -0.2638 0.029 Uiso 1 1 calc R U . . .
C3 C 0.6258(7) 1.3258(12) -0.3166(7) 0.022(2) Uani 1 1 d . . . . .
H3 H 0.7021 1.3676 -0.3190 0.026 Uiso 1 1 calc R U . . .
C4 C 0.5970(7) 1.1666(10) -0.3398(6) 0.0160(18) Uani 1 1 d . . . . .
C5 C 0.3950(8) 1.2041(12) -0.3078(7) 0.022(2) Uani 1 1 d . . . . .
H5 H 0.3181 1.1641 -0.3055 0.027 Uiso 1 1 calc R U . . .
C6 C 0.4834(7) 1.1064(10) -0.3354(6) 0.0129(17) Uani 1 1 d . . . . .
C7 C 0.5926(7) 0.9114(10) -0.3800(6) 0.0155(17) Uani 1 1 d . . . . .
H7 H 0.6153 0.8079 -0.3998 0.019 Uiso 1 1 calc R U . . .
C8 C 0.2603(7) 0.7193(10) -0.1051(6) 0.0152(16) Uani 1 1 d . U . . .
C9 C 0.1628(7) 0.4116(10) 0.0015(6) 0.0161(17) Uani 1 1 d . . . . .
C10 C 0.3832(7) 0.7981(9) -0.2345(6) 0.0150(17) Uani 1 1 d . . . . .
C11 C 0.2695(7) 0.7572(11) -0.2161(6) 0.0158(18) Uani 1 1 d . . . . .
H11 H 0.2004 0.7554 -0.2781 0.019 Uiso 1 1 calc R U . . .
C12 C 0.1330(7) 0.6862(10) -0.0909(6) 0.0145(16) Uani 1 1 d . U . . .
H12A H 0.0964 0.7878 -0.0741 0.017 Uiso 1 1 calc R U . . .
H12B H 0.0829 0.6433 -0.1634 0.017 Uiso 1 1 calc R U . . .
C13 C 0.1599(6) 0.3575(10) 0.1107(7) 0.0150(17) Uani 1 1 d . . . . .
C14 C 0.1847(7) 0.1963(10) 0.1399(6) 0.0139(17) Uani 1 1 d . . . . .
H14 H 0.1833 0.1582 0.2136 0.017 Uiso 1 1 calc R U . . .
C15 C 0.2108(8) 0.1537(12) -0.0504(7) 0.024(2) Uani 1 1 d . . . . .
H15 H 0.2281 0.0819 -0.1053 0.029 Uiso 1 1 calc R U . . .
C16 C 0.2113(8) 0.0940(11) 0.0595(7) 0.022(2) Uani 1 1 d . . . . .
H16 H 0.2298 -0.0152 0.0777 0.026 Uiso 1 1 calc R U . . .
C17 C 0.3578(8) 0.7226(13) -0.0171(7) 0.023(2) Uani 1 1 d . . . . .
H17 H 0.3502 0.6944 0.0570 0.028 Uiso 1 1 calc R U . . .
C18 C 0.4803(7) 0.8031(11) -0.1442(7) 0.0211(19) Uani 1 1 d . . . . .
H18 H 0.5563 0.8315 -0.1567 0.025 Uiso 1 1 calc R U . . .
C19 C 0.1176(7) 0.6102(10) 0.1054(6) 0.0145(17) Uani 1 1 d . . . . .
H19 H 0.0989 0.7148 0.1267 0.017 Uiso 1 1 calc R U . . .
C20 C 0.1864(7) 0.3103(11) -0.0812(7) 0.0190(19) Uani 1 1 d . . . . .
H20 H 0.1858 0.3476 -0.1557 0.023 Uiso 1 1 calc R U . . .
C21 C 0.4716(8) 0.7673(14) -0.0326(7) 0.027(2) Uani 1 1 d . . . . .
H21 H 0.5398 0.7730 0.0301 0.032 Uiso 1 1 calc R U . . .
C22 C 0.3885(7) 0.8307(11) -0.3555(6) 0.0185(19) Uani 1 1 d . . . . .
H22A H 0.4026 0.7289 -0.3922 0.022 Uiso 1 1 calc R U . . .
H22B H 0.3103 0.8741 -0.3984 0.022 Uiso 1 1 calc R U . . .
N1 N 0.1305(6) 0.4843(8) 0.1734(5) 0.0149(16) Uani 1 1 d . . . . .
N2 N 0.1343(6) 0.5712(9) 0.0015(5) 0.0149(14) Uani 1 1 d . U . . .
N3 N 0.4849(6) 0.9459(9) -0.3617(6) 0.0169(16) Uani 1 1 d . . . . .
N4 N 0.6648(6) 1.0398(9) -0.3673(5) 0.0176(16) Uani 1 1 d . . . . .
O1 O 0.0995(5) 0.7636(7) 0.3113(5) 0.0186(13) Uani 1 1 d . . . . .
O2 O 0.1075(5) 0.8793(7) 0.4945(5) 0.0205(14) Uani 1 1 d . . . . .
O3 O -0.0860(5) 0.8152(8) 0.3692(5) 0.0226(14) Uani 1 1 d . . . . .
O4 O 0.0297(5) 1.0369(8) 0.3245(5) 0.0230(14) Uani 1 1 d . . . . .
O1W O 0.1776(5) 0.5740(8) 0.5269(5) 0.0190(13) Uani 1 1 d . . . . .
H1WA H 0.1420 0.5684 0.5808 0.028 Uiso 1 1 d R U . . .
H1WB H 0.2173 0.6607 0.5309 0.028 Uiso 1 1 d R U . . .
O2W O -0.0376(5) 0.4908(8) 0.3278(4) 0.0209(14) Uani 1 1 d . . . . .
H2WB H -0.0715 0.4506 0.3766 0.031 Uiso 1 1 d R U . . .
H2WA H -0.0680 0.5832 0.3114 0.031 Uiso 1 1 d R U . . .
O3W O 0.1711(5) 0.2776(7) 0.4165(5) 0.0188(13) Uani 1 1 d . . . . .
H3WB H 0.2003 0.2806 0.4883 0.028 Uiso 1 1 d R U . . .
H3WA H 0.1033 0.2309 0.4024 0.028 Uiso 1 1 d R U . . .


_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 O2W 2.096(5) . ?
Co1 N4 2.114(7) 2_645 ?
Co1 O1W 2.121(6) . ?
Co1 N1 2.124(6) . ?
Co1 O3W 2.146(6) . ?
Co1 O1 2.156(6) . ?
S1 O4 1.468(7) . ?
S1 O2 1.475(6) . ?
S1 O3 1.494(7) . ?
S1 O1 1.496(6) . ?
C1 C3 1.377(13) . ?
C1 C2 1.387(13) . ?
C1 H1 0.9500 . ?
C2 C5 1.381(14) . ?
C2 H2 0.9500 . ?
C3 C4 1.383(13) . ?
C3 H3 0.9500 . ?
C4 N4 1.401(11) . ?
C4 C6 1.410(12) . ?
C5 C6 1.404(12) . ?
C5 H5 0.9500 . ?
C6 N3 1.380(11) . ?
C7 N3 1.338(11) . ?
C7 N4 1.342(11) . ?
C7 H7 0.9500 . ?
C8 C17 1.344(11) . ?
C8 C11 1.408(11) . ?
C8 C12 1.536(11) . ?
C9 N2 1.373(11) . ?
C9 C20 1.386(12) . ?
C9 C13 1.402(11) . ?
C10 C18 1.358(11) . ?
C10 C11 1.417(12) . ?
C10 C22 1.503(11) . ?
C11 H11 0.9500 . ?
C12 N2 1.471(10) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 N1 1.390(11) . ?
C13 C14 1.404(12) . ?
C14 C16 1.383(12) . ?
C14 H14 0.9500 . ?
C15 C20 1.371(13) . ?
C15 C16 1.417(13) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C21 1.413(13) . ?
C17 H17 0.9500 . ?
C18 C21 1.408(12) . ?
C18 H18 0.9500 . ?
C19 N1 1.320(10) . ?
C19 N2 1.356(10) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 N3 1.483(11) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
N4 Co1 2.114(7) 2_655 ?
O1W H1WA 0.8499 . ?
O1W H1WB 0.8502 . ?
O2W H2WB 0.8503 . ?
O2W H2WA 0.8506 . ?
O3W H3WB 0.8501 . ?
O3W H3WA 0.8500 . ?

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
O2W Co1 N4 177.5(2) . 2_645 ?
O2W Co1 O1W 93.8(2) . . ?
N4 Co1 O1W 88.7(2) 2_645 . ?
O2W Co1 N1 90.3(2) . . ?
N4 Co1 N1 87.3(2) 2_645 . ?
O1W Co1 N1 173.5(3) . . ?
O2W Co1 O3W 88.8(2) . . ?
N4 Co1 O3W 91.1(3) 2_645 . ?
O1W Co1 O3W 82.2(2) . . ?
N1 Co1 O3W 103.0(2) . . ?
O2W Co1 O1 82.5(2) . . ?
N4 Co1 O1 98.0(3) 2_645 . ?
O1W Co1 O1 88.8(2) . . ?
N1 Co1 O1 86.7(2) . . ?
O3W Co1 O1 167.1(2) . . ?
O4 S1 O2 110.7(3) . . ?
O4 S1 O3 109.3(4) . . ?
O2 S1 O3 109.5(3) . . ?
O4 S1 O1 110.7(4) . . ?
O2 S1 O1 107.5(3) . . ?
O3 S1 O1 109.1(4) . . ?
C3 C1 C2 122.7(9) . . ?
C3 C1 H1 118.7 . . ?
C2 C1 H1 118.7 . . ?
C5 C2 C1 122.1(9) . . ?
C5 C2 H2 118.9 . . ?
C1 C2 H2 118.9 . . ?
C1 C3 C4 116.8(8) . . ?
C1 C3 H3 121.6 . . ?
C4 C3 H3 121.6 . . ?
C3 C4 N4 131.0(8) . . ?
C3 C4 C6 120.8(8) . . ?
N4 C4 C6 108.1(7) . . ?
C2 C5 C6 115.6(8) . . ?
C2 C5 H5 122.2 . . ?
C6 C5 H5 122.2 . . ?
N3 C6 C5 132.1(8) . . ?
N3 C6 C4 105.9(7) . . ?
C5 C6 C4 122.0(8) . . ?
N3 C7 N4 112.2(8) . . ?
N3 C7 H7 123.9 . . ?
N4 C7 H7 123.9 . . ?
C17 C8 C11 120.5(8) . . ?
C17 C8 C12 123.3(7) . . ?
C11 C8 C12 116.1(6) . . ?
N2 C9 C20 132.9(8) . . ?
N2 C9 C13 104.7(7) . . ?
C20 C9 C13 122.4(8) . . ?
C18 C10 C11 119.3(7) . . ?
C18 C10 C22 123.8(8) . . ?
C11 C10 C22 116.9(7) . . ?
C8 C11 C10 119.3(7) . . ?
C8 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
N2 C12 C8 111.5(6) . . ?
N2 C12 H12A 109.3 . . ?
C8 C12 H12A 109.3 . . ?
N2 C12 H12B 109.3 . . ?
C8 C12 H12B 109.3 . . ?
H12A C12 H12B 108.0 . . ?
N1 C13 C9 109.3(7) . . ?
N1 C13 C14 131.0(7) . . ?
C9 C13 C14 119.7(8) . . ?
C16 C14 C13 118.9(8) . . ?
C16 C14 H14 120.5 . . ?
C13 C14 H14 120.5 . . ?
C20 C15 C16 123.0(8) . . ?
C20 C15 H15 118.5 . . ?
C16 C15 H15 118.5 . . ?
C14 C16 C15 119.2(8) . . ?
C14 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
C8 C17 C21 121.4(8) . . ?
C8 C17 H17 119.3 . . ?
C21 C17 H17 119.3 . . ?
C10 C18 C21 121.8(8) . . ?
C10 C18 H18 119.1 . . ?
C21 C18 H18 119.1 . . ?
N1 C19 N2 111.4(7) . . ?
N1 C19 H19 124.3 . . ?
N2 C19 H19 124.3 . . ?
C15 C20 C9 116.7(8) . . ?
C15 C20 H20 121.6 . . ?
C9 C20 H20 121.6 . . ?
C18 C21 C17 117.7(7) . . ?
C18 C21 H21 121.1 . . ?
C17 C21 H21 121.1 . . ?
N3 C22 C10 112.0(6) . . ?
N3 C22 H22A 109.2 . . ?
C10 C22 H22A 109.2 . . ?
N3 C22 H22B 109.2 . . ?
C10 C22 H22B 109.2 . . ?
H22A C22 H22B 107.9 . . ?
C19 N1 C13 105.9(6) . . ?
C19 N1 Co1 119.6(5) . . ?
C13 N1 Co1 132.3(5) . . ?
C19 N2 C9 108.7(7) . . ?
C19 N2 C12 124.6(7) . . ?
C9 N2 C12 126.4(7) . . ?
C7 N3 C6 108.2(7) . . ?
C7 N3 C22 126.8(8) . . ?
C6 N3 C22 124.6(7) . . ?
C7 N4 C4 105.6(7) . . ?
C7 N4 Co1 121.6(6) . 2_655 ?
C4 N4 Co1 130.9(5) . 2_655 ?
S1 O1 Co1 128.0(4) . . ?
Co1 O1W H1WA 140.0 . . ?
Co1 O1W H1WB 101.5 . . ?
H1WA O1W H1WB 110.7 . . ?
Co1 O2W H2WB 124.9 . . ?
Co1 O2W H2WA 106.3 . . ?
H2WB O2W H2WA 106.8 . . ?
Co1 O3W H3WB 109.3 . . ?
Co1 O3W H3WA 109.3 . . ?
H3WB O3W H3WA 109.5 . . ?

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
C3 C1 C2 C5 -1.3(14) . . . . ?
C2 C1 C3 C4 0.8(13) . . . . ?
C1 C3 C4 N4 -178.6(8) . . . . ?
C1 C3 C4 C6 -0.2(11) . . . . ?
C1 C2 C5 C6 1.2(12) . . . . ?
C2 C5 C6 N3 179.0(8) . . . . ?
C2 C5 C6 C4 -0.6(11) . . . . ?
C3 C4 C6 N3 -179.5(7) . . . . ?
N4 C4 C6 N3 -0.8(8) . . . . ?
C3 C4 C6 C5 0.2(11) . . . . ?
N4 C4 C6 C5 178.9(7) . . . . ?
C17 C8 C11 C10 0.4(13) . . . . ?
C12 C8 C11 C10 176.4(7) . . . . ?
C18 C10 C11 C8 -1.4(12) . . . . ?
C22 C10 C11 C8 177.5(8) . . . . ?
C17 C8 C12 N2 -34.5(12) . . . . ?
C11 C8 C12 N2 149.5(7) . . . . ?
N2 C9 C13 N1 -0.2(8) . . . . ?
C20 C9 C13 N1 -178.2(7) . . . . ?
N2 C9 C13 C14 179.7(7) . . . . ?
C20 C9 C13 C14 1.7(11) . . . . ?
N1 C13 C14 C16 179.7(7) . . . . ?
C9 C13 C14 C16 -0.1(11) . . . . ?
C13 C14 C16 C15 -1.1(12) . . . . ?
C20 C15 C16 C14 0.9(13) . . . . ?
C11 C8 C17 C21 1.4(15) . . . . ?
C12 C8 C17 C21 -174.4(9) . . . . ?
C11 C10 C18 C21 0.6(14) . . . . ?
C22 C10 C18 C21 -178.2(9) . . . . ?
C16 C15 C20 C9 0.6(13) . . . . ?
N2 C9 C20 C15 -179.2(8) . . . . ?
C13 C9 C20 C15 -1.9(12) . . . . ?
C10 C18 C21 C17 1.1(15) . . . . ?
C8 C17 C21 C18 -2.1(16) . . . . ?
C18 C10 C22 N3 -30.3(12) . . . . ?
C11 C10 C22 N3 150.9(7) . . . . ?
N2 C19 N1 C13 1.3(8) . . . . ?
N2 C19 N1 Co1 166.3(5) . . . . ?
C9 C13 N1 C19 -0.7(8) . . . . ?
C14 C13 N1 C19 179.4(8) . . . . ?
C9 C13 N1 Co1 -162.9(5) . . . . ?
C14 C13 N1 Co1 17.2(12) . . . . ?
N1 C19 N2 C9 -1.5(9) . . . . ?
N1 C19 N2 C12 -176.3(6) . . . . ?
C20 C9 N2 C19 178.7(9) . . . . ?
C13 C9 N2 C19 1.0(8) . . . . ?
C20 C9 N2 C12 -6.7(13) . . . . ?
C13 C9 N2 C12 175.6(6) . . . . ?
C8 C12 N2 C19 105.4(8) . . . . ?
C8 C12 N2 C9 -68.4(9) . . . . ?
N4 C7 N3 C6 0.2(8) . . . . ?
N4 C7 N3 C22 -172.6(7) . . . . ?
C5 C6 N3 C7 -179.3(8) . . . . ?
C4 C6 N3 C7 0.4(8) . . . . ?
C5 C6 N3 C22 -6.4(12) . . . . ?
C4 C6 N3 C22 173.3(6) . . . . ?
C10 C22 N3 C7 102.0(9) . . . . ?
C10 C22 N3 C6 -69.6(9) . . . . ?
N3 C7 N4 C4 -0.6(8) . . . . ?
N3 C7 N4 Co1 165.2(5) . . . 2_655 ?
C3 C4 N4 C7 179.5(8) . . . . ?
C6 C4 N4 C7 0.9(8) . . . . ?
C3 C4 N4 Co1 15.5(12) . . . 2_655 ?
C6 C4 N4 Co1 -163.1(5) . . . 2_655 ?
O4 S1 O1 Co1 175.4(4) . . . . ?
O2 S1 O1 Co1 54.4(5) . . . . ?
O3 S1 O1 Co1 -64.3(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
O3W H3WA O4 0.85 1.96 2.653(8) 138.0 1_545
O2W H2WA O3 0.85 2.09 2.836(9) 146.4 .
O2W H2WA S1 0.85 2.76 3.347(7) 127.9 .
O1W H1WB O2 0.85 2.20 2.675(9) 115.1 .
C22 H22B O2 0.99 2.37 3.319(9) 159.5 1_554
C19 H19 O1 0.95 2.27 2.850(10) 119.0 .
C14 H14 O4 0.95 2.66 3.440(10) 139.9 1_545

_refine_diff_density_max         2.677
_refine_diff_density_min         -0.958
_refine_diff_density_rms         0.201

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_1P
_database_code_depnum_ccdc_archive 'CCDC 1469414'
_audit_update_record             
;
2016-03-18 deposited with the CCDC.
2016-04-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        '(P)-Co(SO4)(1,3-bbix)(H2O)3 '
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H24 Co N4 O7 S'
_chemical_formula_sum            'C22 H24 Co N4 O7 S'
_chemical_formula_weight         547.44

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'
S S 0.1246 0.1234 '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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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+1/2, -z'

_cell_length_a                   11.495(4)
_cell_length_b                   8.412(3)
_cell_length_c                   12.098(4)
_cell_angle_alpha                90
_cell_angle_beta                 103.450(5)
_cell_angle_gamma                90
_cell_volume                     1137.7(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2401
_cell_measurement_theta_min      2.790
_cell_measurement_theta_max      24.928

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.598
_exptl_crystal_F_000             566
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.899
_shelx_estimated_absorpt_T_min   0.774
_shelx_estimated_absorpt_T_max   0.915
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.898
_exptl_absorpt_correction_T_max  0.915
_exptl_absorpt_process_details   'SADABS(Bruker, 2000)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX DUO'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10167
_diffrn_reflns_av_unetI/netI     0.1279
_diffrn_reflns_av_R_equivalents  0.0912
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.822
_diffrn_reflns_theta_max         27.523
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             4537
_reflns_number_gt                3697
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.876
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_fraction_full    0.996

_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       'SMART (Bruker, 2000)'
_computing_cell_refinement       SMART
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_structure_solution    'SHELXTL (Bruker, 2000)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0398P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.09(3)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         4537
_refine_ls_number_parameters     317
_refine_ls_number_restraints     16
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0562
_refine_ls_wR_factor_ref         0.1358
_refine_ls_wR_factor_gt          0.1264
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      0.998
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

_vrf_PLAT987_1                   
;
PROBLEM: The Flack x is >> 0 - Do a BASF/TWIN Refinement Please Check
RESPONSE: The Flack x parameter was refined by means of TWIN and BASF to yield 0.09(3).
;


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 0.85134(6) 0.48224(9) 0.64973(5) 0.0256(2) Uani 1 1 d . . . . .
S1 S 0.96019(13) 0.12471(18) 0.62517(11) 0.0272(3) Uani 1 1 d . . . . .
C1 C 0.4625(8) -0.4169(9) 1.2913(7) 0.055(2) Uani 1 1 d . . . . .
H1 H 0.4445 -0.5229 1.2733 0.066 Uiso 1 1 calc R U . . .
C2 C 0.5766(7) -0.3613(10) 1.2887(7) 0.055(2) Uani 1 1 d . . . . .
H2 H 0.6328 -0.4314 1.2722 0.066 Uiso 1 1 calc R U . . .
C3 C 0.3761(7) -0.3233(9) 1.3190(6) 0.0437(16) Uani 1 1 d . . . . .
H3 H 0.3024 -0.3647 1.3237 0.052 Uiso 1 1 calc R U . . .
C4 C 0.4035(6) -0.1640(8) 1.3396(5) 0.0319(13) Uani 1 1 d . . . . .
C5 C 0.6063(7) -0.2046(10) 1.3101(7) 0.0466(19) Uani 1 1 d . . . . .
H5 H 0.6811 -0.1649 1.3072 0.056 Uiso 1 1 calc R U . . .
C6 C 0.5171(6) -0.1074(8) 1.3367(5) 0.0325(14) Uani 1 1 d . . . . .
C7 C 0.4065(6) 0.0860(8) 1.3783(5) 0.0339(14) Uani 1 1 d . . . . .
H7 H 0.3837 0.1868 1.3966 0.041 Uiso 1 1 calc R U . . .
C8 C 0.7416(5) 0.2827(7) 1.1071(5) 0.0283(12) Uani 1 1 d . U . . .
C9 C 0.8375(6) 0.5894(8) 0.9985(5) 0.0291(13) Uani 1 1 d . . . . .
C10 C 0.6197(6) 0.2010(7) 1.2354(5) 0.0315(13) Uani 1 1 d . . . . .
C11 C 0.7284(5) 0.2428(7) 1.2153(4) 0.0272(12) Uani 1 1 d . . . . .
H11 H 0.7952 0.2447 1.2757 0.033 Uiso 1 1 calc R U . . .
C12 C 0.8655(6) 0.3175(8) 1.0917(5) 0.0309(13) Uani 1 1 d . U . . .
H12A H 0.9135 0.3604 1.1621 0.037 Uiso 1 1 calc R U . . .
H12B H 0.9022 0.2189 1.0759 0.037 Uiso 1 1 calc R U . . .
C13 C 0.8398(5) 0.6440(8) 0.8889(5) 0.0299(12) Uani 1 1 d . . . . .
C14 C 0.8140(6) 0.8023(8) 0.8602(5) 0.0371(14) Uani 1 1 d . . . . .
H14 H 0.8127 0.8400 0.7877 0.044 Uiso 1 1 calc R U . . .
C15 C 0.7906(7) 0.8454(10) 1.0516(6) 0.0445(17) Uani 1 1 d . . . . .
H15 H 0.7744 0.9160 1.1052 0.053 Uiso 1 1 calc R U . . .
C16 C 0.7905(7) 0.9010(9) 0.9428(6) 0.0446(17) Uani 1 1 d . . . . .
H16 H 0.7740 1.0077 0.9258 0.054 Uiso 1 1 calc R U . . .
C17 C 0.6419(6) 0.2773(10) 1.0177(6) 0.0445(17) Uani 1 1 d . . . . .
H17 H 0.6491 0.3023 0.9447 0.053 Uiso 1 1 calc R U . . .
C18 C 0.5202(6) 0.1970(10) 1.1441(6) 0.0438(17) Uani 1 1 d . . . . .
H18 H 0.4456 0.1689 1.1555 0.053 Uiso 1 1 calc R U . . .
C19 C 0.8823(6) 0.3939(8) 0.8955(5) 0.0312(13) Uani 1 1 d . . . . .
H19 H 0.9017 0.2924 0.8750 0.037 Uiso 1 1 calc R U . . .
C20 C 0.8139(6) 0.6908(9) 1.0813(5) 0.0387(16) Uani 1 1 d . . . . .
H20 H 0.8140 0.6543 1.1539 0.046 Uiso 1 1 calc R U . . .
C21 C 0.5333(7) 0.2356(12) 1.0356(6) 0.056(2) Uani 1 1 d . . . . .
H21 H 0.4670 0.2328 0.9745 0.067 Uiso 1 1 calc R U . . .
C22 C 0.6103(6) 0.1665(8) 1.3555(5) 0.0333(14) Uani 1 1 d . . . . .
H22A H 0.6861 0.1248 1.3982 0.040 Uiso 1 1 calc R U . . .
H22B H 0.5950 0.2651 1.3912 0.040 Uiso 1 1 calc R U . . .
N1 N 0.8683(5) 0.5163(6) 0.8264(4) 0.0318(12) Uani 1 1 d . . . . .
N2 N 0.8656(5) 0.4304(6) 0.9994(4) 0.0295(11) Uani 1 1 d . U . . .
N3 N 0.5154(5) 0.0526(7) 1.3609(5) 0.0338(12) Uani 1 1 d . . . . .
N4 N 0.3361(4) -0.0385(7) 1.3670(4) 0.0323(11) Uani 1 1 d . . . . .
O1 O 0.9002(4) 0.2357(6) 0.6881(3) 0.0323(9) Uani 1 1 d . . . . .
O2 O 0.8912(4) 0.1218(6) 0.5057(3) 0.0400(11) Uani 1 1 d . . . . .
O3 O 1.0826(4) 0.1827(6) 0.6291(4) 0.0368(10) Uani 1 1 d . . . . .
O4 O 0.9663(4) -0.0325(7) 0.6742(4) 0.0458(11) Uani 1 1 d . . . . .
O1W O 0.8233(4) 0.4266(5) 0.4748(3) 0.0346(10) Uani 1 1 d . . . . .
H1WA H 0.8590 0.4350 0.4209 0.052 Uiso 1 1 d R U . . .
H1WB H 0.7837 0.3407 0.4708 0.052 Uiso 1 1 d R U . . .
O2W O 1.0361(4) 0.5058(6) 0.6700(3) 0.0362(11) Uani 1 1 d . . . . .
H2WB H 1.0700 0.5460 0.6212 0.054 Uiso 1 1 d R U . . .
H2WA H 1.0664 0.4140 0.6854 0.054 Uiso 1 1 d R U . . .
O3W O 0.8305(4) 0.7214(6) 0.5848(4) 0.0398(11) Uani 1 1 d . . . . .
H3WB H 0.8013 0.7185 0.5135 0.060 Uiso 1 1 d R U . . .
H3WA H 0.8983 0.7671 0.5989 0.060 Uiso 1 1 d R U . . .


_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 O2W 2.090(4) . ?
Co1 O1W 2.118(4) . ?
Co1 N1 2.120(5) . ?
Co1 N4 2.123(5) 2_657 ?
Co1 O3W 2.153(5) . ?
Co1 O1 2.170(5) . ?
S1 O4 1.445(6) . ?
S1 O1 1.473(4) . ?
S1 O2 1.479(4) . ?
S1 O3 1.480(5) . ?
C1 C3 1.370(10) . ?
C1 C2 1.399(12) . ?
C1 H1 0.9300 . ?
C2 C5 1.372(12) . ?
C2 H2 0.9300 . ?
C3 C4 1.386(10) . ?
C3 H3 0.9300 . ?
C4 N4 1.395(8) . ?
C4 C6 1.398(9) . ?
C5 C6 1.407(10) . ?
C5 H5 0.9300 . ?
C6 N3 1.379(8) . ?
C7 N4 1.311(9) . ?
C7 N3 1.346(8) . ?
C7 H7 0.9300 . ?
C8 C17 1.381(9) . ?
C8 C11 1.393(8) . ?
C8 C12 1.507(9) . ?
C9 N2 1.375(9) . ?
C9 C20 1.390(8) . ?
C9 C13 1.409(8) . ?
C10 C11 1.373(8) . ?
C10 C18 1.394(9) . ?
C10 C22 1.510(8) . ?
C11 H11 0.9300 . ?
C12 N2 1.467(7) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.391(10) . ?
C13 N1 1.396(8) . ?
C14 C16 1.373(9) . ?
C14 H14 0.9300 . ?
C15 C20 1.359(11) . ?
C15 C16 1.397(10) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C21 1.362(10) . ?
C17 H17 0.9300 . ?
C18 C21 1.395(10) . ?
C18 H18 0.9300 . ?
C19 N1 1.313(8) . ?
C19 N2 1.350(7) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 N3 1.465(8) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
N4 Co1 2.123(5) 2_647 ?
O1W H1WA 0.8497 . ?
O1W H1WB 0.8500 . ?
O2W H2WB 0.8496 . ?
O2W H2WA 0.8502 . ?
O3W H3WB 0.8503 . ?
O3W H3WA 0.8499 . ?

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
O2W Co1 O1W 93.01(16) . . ?
O2W Co1 N1 90.93(18) . . ?
O1W Co1 N1 173.91(19) . . ?
O2W Co1 N4 178.55(19) . 2_657 ?
O1W Co1 N4 88.37(17) . 2_657 ?
N1 Co1 N4 87.73(19) . 2_657 ?
O2W Co1 O3W 88.74(19) . . ?
O1W Co1 O3W 82.16(17) . . ?
N1 Co1 O3W 102.57(19) . . ?
N4 Co1 O3W 91.0(2) 2_657 . ?
O2W Co1 O1 81.97(19) . . ?
O1W Co1 O1 88.52(17) . . ?
N1 Co1 O1 87.44(17) . . ?
N4 Co1 O1 98.5(2) 2_657 . ?
O3W Co1 O1 166.49(17) . . ?
O4 S1 O1 110.6(3) . . ?
O4 S1 O2 110.5(3) . . ?
O1 S1 O2 107.8(3) . . ?
O4 S1 O3 109.5(3) . . ?
O1 S1 O3 109.3(3) . . ?
O2 S1 O3 109.1(3) . . ?
C3 C1 C2 123.4(7) . . ?
C3 C1 H1 118.3 . . ?
C2 C1 H1 118.3 . . ?
C5 C2 C1 120.7(7) . . ?
C5 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C1 C3 C4 116.9(7) . . ?
C1 C3 H3 121.6 . . ?
C4 C3 H3 121.6 . . ?
C3 C4 N4 131.2(6) . . ?
C3 C4 C6 120.0(6) . . ?
N4 C4 C6 108.8(6) . . ?
C2 C5 C6 116.0(7) . . ?
C2 C5 H5 122.0 . . ?
C6 C5 H5 122.0 . . ?
N3 C6 C4 105.6(6) . . ?
N3 C6 C5 131.5(7) . . ?
C4 C6 C5 122.9(7) . . ?
N4 C7 N3 113.0(6) . . ?
N4 C7 H7 123.5 . . ?
N3 C7 H7 123.5 . . ?
C17 C8 C11 118.4(6) . . ?
C17 C8 C12 123.0(5) . . ?
C11 C8 C12 118.4(5) . . ?
N2 C9 C20 132.5(6) . . ?
N2 C9 C13 105.6(5) . . ?
C20 C9 C13 121.9(6) . . ?
C11 C10 C18 118.6(5) . . ?
C11 C10 C22 119.5(6) . . ?
C18 C10 C22 121.9(6) . . ?
C10 C11 C8 122.1(5) . . ?
C10 C11 H11 119.0 . . ?
C8 C11 H11 119.0 . . ?
N2 C12 C8 112.9(5) . . ?
N2 C12 H12A 109.0 . . ?
C8 C12 H12A 109.0 . . ?
N2 C12 H12B 109.0 . . ?
C8 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
C14 C13 N1 131.7(5) . . ?
C14 C13 C9 119.8(5) . . ?
N1 C13 C9 108.5(5) . . ?
C16 C14 C13 117.7(6) . . ?
C16 C14 H14 121.2 . . ?
C13 C14 H14 121.2 . . ?
C20 C15 C16 121.8(6) . . ?
C20 C15 H15 119.1 . . ?
C16 C15 H15 119.1 . . ?
C14 C16 C15 121.7(7) . . ?
C14 C16 H16 119.1 . . ?
C15 C16 H16 119.1 . . ?
C21 C17 C8 120.5(6) . . ?
C21 C17 H17 119.7 . . ?
C8 C17 H17 119.7 . . ?
C10 C18 C21 119.5(7) . . ?
C10 C18 H18 120.3 . . ?
C21 C18 H18 120.3 . . ?
N1 C19 N2 113.1(6) . . ?
N1 C19 H19 123.5 . . ?
N2 C19 H19 123.5 . . ?
C15 C20 C9 117.1(6) . . ?
C15 C20 H20 121.4 . . ?
C9 C20 H20 121.4 . . ?
C17 C21 C18 120.9(7) . . ?
C17 C21 H21 119.6 . . ?
C18 C21 H21 119.6 . . ?
N3 C22 C10 112.9(5) . . ?
N3 C22 H22A 109.0 . . ?
C10 C22 H22A 109.0 . . ?
N3 C22 H22B 109.0 . . ?
C10 C22 H22B 109.0 . . ?
H22A C22 H22B 107.8 . . ?
C19 N1 C13 105.5(5) . . ?
C19 N1 Co1 120.3(4) . . ?
C13 N1 Co1 132.2(4) . . ?
C19 N2 C9 107.3(5) . . ?
C19 N2 C12 126.0(5) . . ?
C9 N2 C12 126.4(5) . . ?
C7 N3 C6 107.2(6) . . ?
C7 N3 C22 126.8(6) . . ?
C6 N3 C22 125.6(6) . . ?
C7 N4 C4 105.4(5) . . ?
C7 N4 Co1 122.2(5) . 2_647 ?
C4 N4 Co1 130.3(4) . 2_647 ?
S1 O1 Co1 128.6(2) . . ?
Co1 O1W H1WA 139.5 . . ?
Co1 O1W H1WB 101.5 . . ?
H1WA O1W H1WB 112.0 . . ?
Co1 O2W H2WB 125.0 . . ?
Co1 O2W H2WA 107.0 . . ?
H2WB O2W H2WA 106.4 . . ?
Co1 O3W H3WB 109.1 . . ?
Co1 O3W H3WA 109.3 . . ?
H3WB O3W H3WA 110.1 . . ?

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
C3 C1 C2 C5 -2.6(13) . . . . ?
C2 C1 C3 C4 3.3(12) . . . . ?
C1 C3 C4 N4 178.6(7) . . . . ?
C1 C3 C4 C6 -2.9(10) . . . . ?
C1 C2 C5 C6 1.4(12) . . . . ?
C3 C4 C6 N3 -179.7(6) . . . . ?
N4 C4 C6 N3 -0.9(7) . . . . ?
C3 C4 C6 C5 2.0(10) . . . . ?
N4 C4 C6 C5 -179.2(6) . . . . ?
C2 C5 C6 N3 -179.0(7) . . . . ?
C2 C5 C6 C4 -1.1(11) . . . . ?
C18 C10 C11 C8 0.6(10) . . . . ?
C22 C10 C11 C8 -177.2(6) . . . . ?
C17 C8 C11 C10 -0.9(10) . . . . ?
C12 C8 C11 C10 -176.4(6) . . . . ?
C17 C8 C12 N2 34.2(9) . . . . ?
C11 C8 C12 N2 -150.6(6) . . . . ?
N2 C9 C13 C14 179.6(6) . . . . ?
C20 C9 C13 C14 -2.3(10) . . . . ?
N2 C9 C13 N1 0.5(7) . . . . ?
C20 C9 C13 N1 178.7(6) . . . . ?
N1 C13 C14 C16 -179.3(7) . . . . ?
C9 C13 C14 C16 2.0(10) . . . . ?
C13 C14 C16 C15 -0.8(11) . . . . ?
C20 C15 C16 C14 -0.1(12) . . . . ?
C11 C8 C17 C21 0.7(12) . . . . ?
C12 C8 C17 C21 175.9(8) . . . . ?
C11 C10 C18 C21 -0.1(11) . . . . ?
C22 C10 C18 C21 177.6(7) . . . . ?
C16 C15 C20 C9 -0.1(11) . . . . ?
N2 C9 C20 C15 178.9(7) . . . . ?
C13 C9 C20 C15 1.3(10) . . . . ?
C8 C17 C21 C18 -0.2(14) . . . . ?
C10 C18 C21 C17 -0.1(14) . . . . ?
C11 C10 C22 N3 -151.1(6) . . . . ?
C18 C10 C22 N3 31.2(9) . . . . ?
N2 C19 N1 C13 -0.2(8) . . . . ?
N2 C19 N1 Co1 -166.4(4) . . . . ?
C14 C13 N1 C19 -179.1(7) . . . . ?
C9 C13 N1 C19 -0.2(7) . . . . ?
C14 C13 N1 Co1 -15.2(10) . . . . ?
C9 C13 N1 Co1 163.7(4) . . . . ?
N1 C19 N2 C9 0.5(8) . . . . ?
N1 C19 N2 C12 174.8(6) . . . . ?
C20 C9 N2 C19 -178.5(7) . . . . ?
C13 C9 N2 C19 -0.6(7) . . . . ?
C20 C9 N2 C12 7.3(11) . . . . ?
C13 C9 N2 C12 -174.8(5) . . . . ?
C8 C12 N2 C19 -104.4(7) . . . . ?
C8 C12 N2 C9 68.8(8) . . . . ?
N4 C7 N3 C6 -0.4(7) . . . . ?
N4 C7 N3 C22 173.3(6) . . . . ?
C4 C6 N3 C7 0.8(7) . . . . ?
C5 C6 N3 C7 178.9(7) . . . . ?
C4 C6 N3 C22 -173.0(5) . . . . ?
C5 C6 N3 C22 5.1(11) . . . . ?
C10 C22 N3 C7 -102.1(7) . . . . ?
C10 C22 N3 C6 70.4(8) . . . . ?
N3 C7 N4 C4 -0.1(7) . . . . ?
N3 C7 N4 Co1 -165.2(4) . . . 2_647 ?
C3 C4 N4 C7 179.3(7) . . . . ?
C6 C4 N4 C7 0.6(7) . . . . ?
C3 C4 N4 Co1 -17.3(10) . . . 2_647 ?
C6 C4 N4 Co1 164.1(4) . . . 2_647 ?
O4 S1 O1 Co1 -174.9(3) . . . . ?
O2 S1 O1 Co1 -54.0(4) . . . . ?
O3 S1 O1 Co1 64.5(4) . . . . ?

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
O3W H3WA O4 0.85 1.99 2.666(7) 136.1 1_565
O3W H3WB O3 0.85 2.43 3.000(6) 124.8 2_756
O2W H2WA O3 0.85 2.08 2.836(7) 147.1 .
O2W H2WA S1 0.85 2.74 3.334(5) 127.8 .
O2W H2WB O2 0.85 1.81 2.645(6) 166.5 2_756
O2W H2WB S1 0.85 2.99 3.718(4) 144.5 2_756
O1W H1WB O2 0.85 2.20 2.681(7) 115.6 .
O1W H1WA O4 0.85 2.55 3.353(6) 157.8 2_756
O1W H1WA O3 0.85 2.31 2.832(6) 119.7 2_756
O1W H1WA S1 0.85 2.78 3.439(4) 135.9 2_756
C22 H22A O2 0.97 2.41 3.337(8) 159.3 1_556
C20 H20 O3 0.93 2.63 3.429(8) 144.5 2_757
C19 H19 O1 0.93 2.31 2.890(7) 120.2 .
C12 H12A O4 0.97 2.32 3.286(8) 177.6 2_757
C7 H7 O3W 0.93 2.54 3.080(8) 117.3 2_647
C3 H3 O1 0.93 2.45 3.195(9) 137.3 2_647
O3W H3WA O4 0.85 1.99 2.666(7) 136.1 1_565
O3W H3WB O3 0.85 2.43 3.000(6) 124.8 2_756
O2W H2WA O3 0.85 2.08 2.836(7) 147.1 .
O2W H2WB O2 0.85 1.81 2.645(6) 166.5 2_756
O1W H1WB O2 0.85 2.20 2.681(7) 115.6 .
O1W H1WA O4 0.85 2.55 3.353(6) 157.8 2_756
O1W H1WA O3 0.85 2.31 2.832(6) 119.7 2_756
C22 H22A O2 0.97 2.41 3.337(8) 159.3 1_556
C19 H19 O1 0.93 2.31 2.890(7) 120.2 .
C12 H12A O4 0.97 2.32 3.286(8) 177.6 2_757
C7 H7 O3W 0.93 2.54 3.080(8) 117.3 2_647
C3 H3 O1 0.93 2.45 3.195(9) 137.3 2_647
C3 H3 O1 0.93 2.45 3.195(9) 137.3 2_647
C7 H7 O3W 0.93 2.54 3.080(8) 117.3 2_647
C12 H12A O4 0.97 2.32 3.286(8) 177.6 2_757
C19 H19 O1 0.93 2.31 2.890(7) 120.2 .
C22 H22A O2 0.97 2.41 3.337(8) 159.3 1_556
O1W H1WA O3 0.85 2.31 2.832(6) 119.7 2_756
O1W H1WA O4 0.85 2.55 3.353(6) 157.8 2_756
O1W H1WB O2 0.85 2.20 2.681(7) 115.6 .
O2W H2WB O2 0.85 1.81 2.645(6) 166.5 2_756
O2W H2WA O3 0.85 2.08 2.836(7) 147.1 .
O3W H3WB O3 0.85 2.43 3.000(6) 124.8 2_756
O3W H3WA O4 0.85 1.99 2.666(7) 136.1 1_565

_refine_diff_density_max         0.623
_refine_diff_density_min         -0.800
_refine_diff_density_rms         0.087

_shelxl_version_number           2013-4

