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

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

data_1_sq
_audit_block_doi                 10.5517/cc1knpyv
_database_code_depnum_ccdc_archive 'CCDC 1449868'
_audit_update_record             
;
2016-08-23 deposited with the CCDC.
2016-08-26 downloaded from the CCDC.
;
_audit_creation_date             2016-08-17
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.07.26 svn.r3321 for OlexSys, GUI svn.r5206)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H9 Cu2 O12'
_chemical_formula_sum            'C23 H9 Cu2 O12'
_chemical_formula_weight         604.38
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      hexagonal
_space_group_IT_number           194
_space_group_name_H-M_alt        'P 63/m m c'
_space_group_name_Hall           '-P 6c 2c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x-y, x, z+1/2'
'-y, x-y, z'
'-x, -y, z+1/2'
'-x+y, -x, z'
'y, -x+y, z+1/2'
'-y, -x, -z+1/2'
'x-y, -y, -z'
'x, x-y, -z+1/2'
'y, x, -z'
'-x+y, y, -z+1/2'
'-x, -x+y, -z'
'-x, -y, -z'
'-x+y, -x, -z-1/2'
'y, -x+y, -z'
'x, y, -z-1/2'
'x-y, x, -z'
'-y, x-y, -z-1/2'
'y, x, z-1/2'
'-x+y, y, z'
'-x, -x+y, z-1/2'
'-y, -x, z'
'x-y, -y, z-1/2'
'x, x-y, z'

_cell_length_a                   18.5085(6)
_cell_length_b                   18.5085(6)
_cell_length_c                   22.9306(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     6802.8(5)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    5011
_cell_measurement_temperature    296
_cell_measurement_theta_max      52.800
_cell_measurement_theta_min      2.757
_shelx_estimated_absorpt_T_max   0.867
_shelx_estimated_absorpt_T_min   0.843
_exptl_absorpt_coefficient_mu    1.470
_exptl_absorpt_correction_T_max  0.7518
_exptl_absorpt_correction_T_min  0.6039
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1113 before and 0.0412 after correction.
The Ratio of minimum to maximum transmission is 0.8033.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    0.885
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1806
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            19853
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        60.190
_diffrn_reflns_theta_max         60.190
_diffrn_reflns_theta_min         2.757
_diffrn_ambient_temperature      296.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1284
_reflns_number_total             1880
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.774
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     115
_refine_ls_number_reflns         1880
_refine_ls_number_restraints     112
_refine_ls_R_factor_all          0.0901
_refine_ls_R_factor_gt           0.0688
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1733P)²+2.8878P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2346
_refine_ls_wR_factor_ref         0.2723
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 C8-C10
 1.5 with sigma of 0.01
 C10-O3 = C10-O4
 1.25 with sigma of 0.01
 O3-O4
 2.2 with sigma of 0.01
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(O1WB)=Sof(H1WC)=Sof(H1WD)=0.5*(1-FVAR(2))
 Sof(O1WA)=Sof(H1WA)=Sof(H1WB)=0.5*FVAR(2)
 Fixed Sof: H8(0.25) O3(0.25) O4(0.25) C10(0.25)
5.a Riding coordinates:
 O1WA(H1WA,H1WB), C8(H8), O1WB(H1WC,H1WD)
5.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C3(H3), C7(H7), C9(H9)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.47648(3) 0.52352(3) 0.45188(5) 0.1004(6) Uani 1 2 d S TU P . .
O1 O 0.5186(2) 0.6284(2) 0.4935(2) 0.1245(14) Uani 1 1 d . U . . .
O2 O 0.5602(3) 0.5901(2) 0.5738(2) 0.1218(13) Uani 1 1 d . U . . .
O1WA O 0.449(2) 0.551(2) 0.3643(16) 0.161(9) Uani 0.59(11) 2 d S TU P A 1
H1WA H 0.4228 0.5772 0.3582 0.241 Uiso 0.59(11) 2 d RS T P A 1
H1WB H 0.4618 0.5382 0.3318 0.241 Uiso 0.59(11) 2 d RS T P A 1
C1 C 0.5506(4) 0.6415(4) 0.5435(3) 0.1095(16) Uani 1 1 d . U . . .
C2 C 0.5805(3) 0.7257(3) 0.5691(3) 0.1089(15) Uani 1 1 d . U . . .
C4 C 0.6306(4) 0.7514(4) 0.6175(3) 0.1137(16) Uani 1 1 d . U . . .
H4 H 0.6476 0.7163 0.6337 0.136 Uiso 1 1 calc R . . . .
C3 C 0.5570(5) 0.7785(2) 0.5438(4) 0.110(2) Uani 1 2 d S TU P . .
H3 H 0.5254 0.7627 0.5098 0.132 Uiso 1 2 calc RS T P . .
C5 C 0.6565(5) 0.8283(2) 0.6426(4) 0.113(2) Uani 1 2 d S TU P . .
C6 C 0.7073(5) 0.8537(2) 0.6987(4) 0.112(2) Uani 1 2 d S TU P . .
C7 C 0.6645(8) 0.8322(4) 0.7500 0.111(3) Uani 1 4 d S TU P . .
H7 H 0.6065 0.8032 0.7500 0.133 Uiso 1 4 calc RS T P . .
C8 C 0.7930(6) 0.8965(3) 0.6976(5) 0.160(4) Uani 1 2 d DS TU P . .
H8 H 0.8221 0.9111 0.6625 0.191 Uiso 0.5 2 d RS T P B 1
O3 O 0.8255(15) 0.9127(7) 0.5890(10) 0.39(2) Uani 0.5 2 d DS TU P C 2
O4 O 0.9194(13) 0.9597(6) 0.6578(12) 0.58(4) Uani 0.5 2 d DS TU P C 2
C10 C 0.8446(12) 0.9223(6) 0.6423(8) 0.202(10) Uani 0.5 2 d DS TU P C 2
C9 C 0.8323(10) 0.9161(5) 0.7500 0.190(7) Uani 1 4 d S TU P C .
H9 H 0.8903 0.9451 0.7500 0.228 Uiso 1 4 calc RS T P . .
O1WB O 0.4312(17) 0.5688(17) 0.382(3) 0.135(11) Uani 0.41(11) 2 d S TU P A 2
H1WC H 0.4050 0.5950 0.3878 0.203 Uiso 0.41(11) 2 d RS T P A 2
H1WD H 0.4361 0.5639 0.3457 0.203 Uiso 0.41(11) 2 d RS T P A 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
Cu1 Cu1 2.673(2) 13_666 ?
Cu1 O1 1.942(4) . ?
Cu1 O1 1.942(4) 22_665 ?
Cu1 O2 1.950(4) 13_666 ?
Cu1 O2 1.950(4) 10_556 ?
Cu1 O1WA 2.194(18) . ?
Cu1 O1WB 2.16(3) . ?
O1 C1 1.259(7) . ?
O2 Cu1 1.950(4) 13_666 ?
O2 C1 1.261(7) . ?
O1WA H1WA 0.8500 . ?
O1WA H1WB 0.8501 . ?
C1 C2 1.490(8) . ?
C2 C4 1.369(8) . ?
C2 C3 1.380(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.380(7) . ?
C3 C2 1.380(7) 24_565 ?
C3 H3 0.9300 . ?
C5 C4 1.380(7) 24_565 ?
C5 C6 1.523(11) . ?
C6 C7 1.362(10) . ?
C6 C8 1.373(11) . ?
C7 C6 1.362(10) 16_557 ?
C7 H7 0.9300 . ?
C8 H8 0.9295 . ?
C8 C10 1.514(10) . ?
C8 C9 1.357(12) . ?
O3 C10 1.259(10) . ?
O4 C10 1.251(10) . ?
C9 C8 1.357(12) 16_557 ?
C9 H9 0.9300 . ?
O1WB H1WC 0.8499 . ?
O1WB H1WD 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
O1 Cu1 Cu1 83.51(14) . 13_666 ?
O1 Cu1 Cu1 83.51(14) 22_665 13_666 ?
O1 Cu1 O1 88.9(2) . 22_665 ?
O1 Cu1 O2 88.64(18) . 10_556 ?
O1 Cu1 O2 167.33(19) . 13_666 ?
O1 Cu1 O2 88.64(18) 22_665 13_666 ?
O1 Cu1 O2 167.33(19) 22_665 10_556 ?
O1 Cu1 O1WA 104.0(14) 22_665 . ?
O1 Cu1 O1WA 104.0(14) . . ?
O1 Cu1 O1WB 90.9(16) . . ?
O1 Cu1 O1WB 90.9(16) 22_665 . ?
O2 Cu1 Cu1 83.86(13) 13_666 13_666 ?
O2 Cu1 Cu1 83.86(13) 10_556 13_666 ?
O2 Cu1 O2 91.0(2) 13_666 10_556 ?
O2 Cu1 O1WA 88.7(15) 13_666 . ?
O2 Cu1 O1WA 88.7(15) 10_556 . ?
O2 Cu1 O1WB 101.6(15) 10_556 . ?
O2 Cu1 O1WB 101.6(15) 13_666 . ?
O1WA Cu1 Cu1 169(2) . 13_666 ?
O1WB Cu1 Cu1 172(2) . 13_666 ?
C1 O1 Cu1 123.7(4) . . ?
C1 O2 Cu1 122.8(4) . 13_666 ?
Cu1 O1WA H1WA 123.1 . . ?
Cu1 O1WA H1WB 127.4 . . ?
H1WA O1WA H1WB 109.5 . . ?
O1 C1 O2 126.0(6) . . ?
O1 C1 C2 117.0(5) . . ?
O2 C1 C2 117.0(6) . . ?
C4 C2 C1 121.0(5) . . ?
C4 C2 C3 119.6(6) . . ?
C3 C2 C1 119.4(6) . . ?
C2 C4 H4 119.3 . . ?
C2 C4 C5 121.4(6) . . ?
C5 C4 H4 119.3 . . ?
C2 C3 C2 119.8(8) . 24_565 ?
C2 C3 H3 120.1 . . ?
C2 C3 H3 120.1 24_565 . ?
C4 C5 C4 118.1(8) 24_565 . ?
C4 C5 C6 120.9(4) . . ?
C4 C5 C6 120.9(4) 24_565 . ?
C7 C6 C5 117.4(7) . . ?
C7 C6 C8 121.4(10) . . ?
C8 C6 C5 121.2(9) . . ?
C6 C7 C6 119.4(12) 16_557 . ?
C6 C7 H7 120.3 . . ?
C6 C7 H7 120.3 16_557 . ?
C6 C8 H8 121.3 . . ?
C6 C8 C10 124.2(12) . . ?
C9 C8 C6 116.5(13) . . ?
C9 C8 H8 122.2 . . ?
C9 C8 C10 119.2(13) . . ?
O3 C10 C8 133(2) . . ?
O4 C10 C8 106.5(18) . . ?
O4 C10 O3 120.7(13) . . ?
C8 C9 C8 124.7(16) . 16_557 ?
C8 C9 H9 117.6 . . ?
C8 C9 H9 117.6 16_557 . ?
Cu1 O1WB H1WC 123.3 . . ?
Cu1 O1WB H1WD 127.2 . . ?
H1WC O1WB H1WD 109.5 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'

# start Validation Reply Form
_vrf_THETM01_1_sq                
;
PROBLEM:  The value of sine(theta_max)/wavelength is less than 0.575   
RESPONSE: The structure contains a huge void. The refections with a higher 
theta were too weak to observe. So the refections with resolution higher than
0.89 couldn't be recorded.
;

_vrf_PLAT420_1_sq                
;
PROBLEM: D-H Without Acceptor      >O1WA   -- >H1WA   ...     Please Check 
D-H Without Acceptor      >O1WA   -- >H1WB   ...     Please Check
RESPONSE: The highly disordered solvents in the void were squeezed. The 
acceptors for O1WA should in the huge void. So the acceptors for O1WA 
couldn't located.
;


# end Validation Reply Form
####################################################################### 
# 
# 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_2_sq
_audit_block_doi                 10.5517/ccdc.csd.cc1lj64g
_database_code_depnum_ccdc_archive 'CCDC 1475325'
_audit_update_record             
;
2016-08-23 deposited with the CCDC.
2016-08-26 downloaded from the CCDC.
;
_audit_creation_date             2016-08-17
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.07.26 svn.r3321 for OlexSys, GUI svn.r5206)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H18 Co2 N O11, C2 H8 N'
_chemical_formula_sum            'C29 H26 Co2 N2 O11'
_chemical_formula_weight         696.38
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.162(2)
_cell_length_b                   15.986(4)
_cell_length_c                   23.971(6)
_cell_angle_alpha                90
_cell_angle_beta                 99.582(4)
_cell_angle_gamma                90
_cell_volume                     3839.6(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5989
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      28.215
_cell_measurement_theta_min      2.399
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.913
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5858
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0997 before and 0.0580 after correction.
The Ratio of minimum to maximum transmission is 0.7856.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_av_unetI/netI     0.0645
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            23117
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.422
_diffrn_reflns_theta_min         1.538
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6525
_reflns_number_total             9276
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.338
_refine_diff_density_min         -0.735
_refine_diff_density_rms         0.105
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     441
_refine_ls_number_reflns         9276
_refine_ls_number_restraints     107
_refine_ls_R_factor_all          0.0869
_refine_ls_R_factor_gt           0.0622
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1295P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1857
_refine_ls_wR_factor_ref         0.2023
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H,H,H) groups
2. Restrained distances
 C24-C25A
 1.5 with sigma of 0.02
 C25-O11
 2.6 with sigma of 0.02
 C28-N2
 1.4 with sigma of 0.02
 N2-C29
 1.4 with sigma of 0.02
 C28-C29
 2.5 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(N2) \\sim Ueq, Uanis(C29) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.01
Uanis(C25) \\sim Ueq, Uanis(C25A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.01
Uanis(C28) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.01
Uanis(C28) \\sim Ueq, Uanis(N2) \\sim Ueq, Uanis(C29) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.01
4. Rigid body (RIGU) restrains
 O11, O11A, N1, N1A, C24, C25, C25A, C26, C26A, C27
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N2, C28, C29
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(O11A)=Sof(C25A)=Sof(H25D)=Sof(H25E)=Sof(H25F)=Sof(C26A)=Sof(H26D)=
 Sof(H26E)=Sof(H26F)=1-FVAR(1)
 Sof(O11)=Sof(C25)=Sof(H25A)=Sof(H25B)=Sof(H25C)=Sof(C26)=Sof(H26A)=Sof(H26B)=
 Sof(H26C)=FVAR(1)
 Sof(N1A)=Sof(H27D)=Sof(H27E)=Sof(H27F)=1-FVAR(2)
 Sof(N1)=Sof(H27A)=Sof(H27B)=Sof(H27C)=FVAR(2)
6.a Secondary CH2 refined with riding coordinates:
 N2(H2A,H2B)
6.b Me refined with riding coordinates:
 C27(H27A,H27B,H27C), C27(H27D,H27E,H27F)
6.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C7(H7), C10(H10), C12(H12), C13(H13), C17(H17), C19(H19),
 C21(H21)
6.d Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C25A(H25D,H25E,H25F), C26(H26A,H26B,H26C), C26A(H26D,
 H26E,H26F), C28(H28A,H28B,H28C), C29(H29A,H29B,H29C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 1.16900(4) 0.49825(3) 0.66578(2) 0.02660(15) Uani 1 1 d . . . . .
Co2 Co 0.98648(5) 0.61151(3) 0.75450(2) 0.03140(16) Uani 1 1 d . . . . .
O1 O 0.9951(3) 0.44422(18) 0.63900(14) 0.0508(7) Uani 1 1 d . . . . .
O2 O 0.9049(3) 0.5273(2) 0.69528(13) 0.0551(8) Uani 1 1 d . . . . .
O3 O 0.4064(3) 0.52590(19) 0.68027(14) 0.0549(8) Uani 1 1 d . . . . .
O4 O 0.2937(2) 0.42929(17) 0.62922(12) 0.0421(6) Uani 1 1 d . . . . .
O5 O 0.4866(4) 0.17974(17) 0.66629(12) 0.0567(8) Uani 1 1 d . . . . .
O6 O 0.6464(4) 0.0893(2) 0.68479(13) 0.0619(9) Uani 1 1 d . . . . .
O7 O 0.6134(3) -0.02442(16) 0.30258(11) 0.0474(7) Uani 1 1 d . . . . .
O8 O 0.7068(3) 0.04886(19) 0.24208(11) 0.0551(8) Uani 1 1 d . . . . .
O9 O 0.8614(3) 0.33199(16) 0.28078(10) 0.0462(7) Uani 1 1 d . . . . .
O10 O 0.8533(3) 0.38731(14) 0.36527(11) 0.0371(6) Uani 1 1 d . . . . .
O11 O 0.8342(7) 0.6865(4) 0.7104(3) 0.0574(18) Uani 0.598(10) 1 d D U P A 1
O11A O 0.9054(14) 0.7241(8) 0.7206(5) 0.078(3) Uani 0.402(10) 1 d . U P A 2
N1 N 0.6922(12) 0.7888(7) 0.6866(5) 0.112(4) Uani 0.592(13) 1 d . U P A 1
N1A N 0.7751(13) 0.8355(7) 0.7035(4) 0.066(3) Uani 0.408(13) 1 d . U P A 2
C1 C 0.8987(3) 0.4697(2) 0.66071(15) 0.0336(8) Uani 1 1 d . . . . .
C2 C 0.7671(3) 0.4263(2) 0.64447(14) 0.0275(7) Uani 1 1 d . . . . .
C3 C 0.7623(3) 0.3496(2) 0.61688(14) 0.0295(7) Uani 1 1 d . . . . .
H3 H 0.8405 0.3257 0.6089 0.035 Uiso 1 1 calc R . . . .
C4 C 0.6413(3) 0.3084(2) 0.60116(13) 0.0277(7) Uani 1 1 d . . . . .
C5 C 0.5249(3) 0.3459(2) 0.61233(13) 0.0273(7) Uani 1 1 d . . . . .
H5 H 0.4434 0.3190 0.6017 0.033 Uiso 1 1 calc R . . . .
C6 C 0.5290(3) 0.4229(2) 0.63904(14) 0.0296(7) Uani 1 1 d . . . . .
C7 C 0.6510(3) 0.4620(2) 0.65624(14) 0.0302(7) Uani 1 1 d . . . . .
H7 H 0.6546 0.5125 0.6758 0.036 Uiso 1 1 calc R . . . .
C8 C 0.4032(4) 0.4628(2) 0.65085(15) 0.0360(8) Uani 1 1 d . . . . .
C9 C 0.6388(4) 0.2273(2) 0.56948(14) 0.0309(7) Uani 1 1 d . . . . .
C10 C 0.6721(4) 0.2294(2) 0.51589(14) 0.0342(8) Uani 1 1 d . . . . .
H10 H 0.6903 0.2809 0.5009 0.041 Uiso 1 1 calc R . . . .
C11 C 0.6797(4) 0.1586(2) 0.48350(15) 0.0398(9) Uani 1 1 d . . . . .
C12 C 0.6572(6) 0.0821(2) 0.50787(18) 0.0584(13) Uani 1 1 d . . . . .
H12 H 0.6641 0.0330 0.4877 0.070 Uiso 1 1 calc R . . . .
C13 C 0.6249(6) 0.0779(2) 0.56150(18) 0.0628(15) Uani 1 1 d . . . . .
H13 H 0.6098 0.0261 0.5768 0.075 Uiso 1 1 calc R . . . .
C14 C 0.6145(4) 0.1496(2) 0.59282(16) 0.0439(10) Uani 1 1 d . . . . .
C15 C 0.5797(5) 0.1393(2) 0.65217(17) 0.0442(10) Uani 1 1 d . . . . .
C16 C 0.7109(4) 0.1649(2) 0.42457(15) 0.0350(8) Uani 1 1 d . . . . .
C17 C 0.7641(4) 0.2384(2) 0.40593(15) 0.0367(8) Uani 1 1 d . . . . .
H17 H 0.7818 0.2831 0.4308 0.044 Uiso 1 1 calc R . . . .
C18 C 0.7912(3) 0.2465(2) 0.35113(14) 0.0304(7) Uani 1 1 d . . . . .
C19 C 0.7650(4) 0.1789(2) 0.31413(14) 0.0315(7) Uani 1 1 d . . . . .
H19 H 0.7840 0.1831 0.2776 0.038 Uiso 1 1 calc R . . . .
C20 C 0.7110(4) 0.10577(19) 0.33121(14) 0.0296(7) Uani 1 1 d . . . . .
C21 C 0.6836(4) 0.0989(2) 0.38597(15) 0.0348(8) Uani 1 1 d . . . . .
H21 H 0.6466 0.0497 0.3971 0.042 Uiso 1 1 calc R . . . .
C22 C 0.8398(3) 0.3272(2) 0.33056(15) 0.0328(8) Uani 1 1 d . . . . .
C23 C 0.6739(4) 0.0368(2) 0.28881(14) 0.0307(7) Uani 1 1 d . . . . .
C24 C 0.7974(6) 0.7585(3) 0.7104(2) 0.0693(13) Uani 1 1 d D U . . .
C25 C 0.5968(15) 0.7275(12) 0.6625(8) 0.161(6) Uani 0.598(10) 1 d D U P A 1
H25A H 0.6336 0.6725 0.6701 0.242 Uiso 0.598(10) 1 calc GR . P A 1
H25B H 0.5755 0.7359 0.6223 0.242 Uiso 0.598(10) 1 calc GR . P A 1
H25C H 0.5172 0.7329 0.6789 0.242 Uiso 0.598(10) 1 calc GR . P A 1
C25A C 0.6681(17) 0.7120(13) 0.7178(9) 0.113(6) Uani 0.402(10) 1 d D U P A 2
H25D H 0.6461 0.6717 0.6879 0.169 Uiso 0.402(10) 1 calc GR . P A 2
H25E H 0.5965 0.7515 0.7164 0.169 Uiso 0.402(10) 1 calc GR . P A 2
H25F H 0.6814 0.6838 0.7536 0.169 Uiso 0.402(10) 1 calc GR . P A 2
C26 C 0.9141(10) 0.8226(6) 0.7314(4) 0.071(3) Uani 0.598(10) 1 d . U P A 1
H26A H 0.9312 0.8236 0.7720 0.107 Uiso 0.598(10) 1 calc GR . P A 1
H26B H 0.8884 0.8774 0.7174 0.107 Uiso 0.598(10) 1 calc GR . P A 1
H26C H 0.9934 0.8055 0.7176 0.107 Uiso 0.598(10) 1 calc GR . P A 1
C26A C 0.9148(19) 0.8752(13) 0.7054(9) 0.101(6) Uani 0.402(10) 1 d . U P A 2
H26D H 0.9813 0.8320 0.7098 0.152 Uiso 0.402(10) 1 calc GR . P A 2
H26E H 0.9325 0.9133 0.7367 0.152 Uiso 0.402(10) 1 calc GR . P A 2
H26F H 0.9172 0.9050 0.6708 0.152 Uiso 0.402(10) 1 calc GR . P A 2
C27 C 0.6548(8) 0.8802(5) 0.6930(4) 0.130(3) Uani 1 1 d . U . . .
H27A H 0.5687 0.8908 0.6709 0.194 Uiso 0.592(13) 1 calc R . P A 1
H27B H 0.6521 0.8918 0.7321 0.194 Uiso 0.592(13) 1 calc R . P A 1
H27C H 0.7200 0.9155 0.6801 0.194 Uiso 0.592(13) 1 calc R . P A 1
H27D H 0.6734 0.9387 0.6900 0.194 Uiso 0.408(13) 1 calc R . P A 2
H27E H 0.6025 0.8610 0.6583 0.194 Uiso 0.408(13) 1 calc R . P A 2
H27F H 0.6061 0.8714 0.7235 0.194 Uiso 0.408(13) 1 calc R . P A 2
N2 N 0.6731(11) 0.3378(7) 0.1596(5) 0.198(4) Uani 1 1 d D U . . .
H2A H 0.6672 0.3547 0.1239 0.238 Uiso 1 1 calc R . . . .
H2B H 0.7534 0.3520 0.1779 0.238 Uiso 1 1 calc R . . . .
C28 C 0.5617(16) 0.3842(10) 0.1879(7) 0.258(7) Uani 1 1 d D U . . .
H28A H 0.5023 0.4140 0.1593 0.387 Uiso 1 1 calc GR . . . .
H28B H 0.6037 0.4230 0.2159 0.387 Uiso 1 1 calc GR . . . .
H28C H 0.5121 0.3437 0.2054 0.387 Uiso 1 1 calc GR . . . .
C29 C 0.6593(11) 0.2503(6) 0.1607(4) 0.154(4) Uani 1 1 d D U . . .
H29A H 0.5910 0.2330 0.1303 0.232 Uiso 1 1 calc GR . . . .
H29B H 0.6351 0.2337 0.1962 0.232 Uiso 1 1 calc GR . . . .
H29C H 0.7424 0.2245 0.1565 0.232 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 O1 1.976(3) . ?
Co1 O4 1.990(2) 1_655 ?
Co1 O8 1.956(3) 4_666 ?
Co1 O10 1.974(2) 3_766 ?
Co2 O2 2.030(3) . ?
Co2 O5 2.167(3) 2_656 ?
Co2 O6 2.173(3) 2_656 ?
Co2 O7 2.106(3) 4_666 ?
Co2 O9 2.087(3) 3_766 ?
Co2 O11 2.099(5) . ?
Co2 O11A 2.087(10) . ?
Co2 C15 2.481(4) 2_656 ?
O1 C1 1.252(4) . ?
O2 C1 1.233(5) . ?
O3 C8 1.228(5) . ?
O4 Co1 1.990(2) 1_455 ?
O4 C8 1.265(5) . ?
O5 Co2 2.167(3) 2_646 ?
O5 C15 1.239(5) . ?
O6 Co2 2.173(3) 2_646 ?
O6 C15 1.238(5) . ?
O7 Co2 2.106(3) 4_565 ?
O7 C23 1.230(4) . ?
O8 Co1 1.956(3) 4_565 ?
O8 C23 1.236(4) . ?
O9 Co2 2.087(2) 3_766 ?
O9 C22 1.251(4) . ?
O10 Co1 1.974(2) 3_766 ?
O10 C22 1.263(4) . ?
O11 C24 1.209(7) . ?
O11A C24 1.216(12) . ?
N1 C24 1.224(11) . ?
N1 C25 1.43(2) . ?
N1 C27 1.524(13) . ?
N1A C24 1.258(12) . ?
N1A C26A 1.55(2) . ?
N1A C27 1.402(12) . ?
C1 C2 1.499(5) . ?
C2 C3 1.390(5) . ?
C2 C7 1.381(4) . ?
C3 C4 1.391(5) . ?
C4 C5 1.391(4) . ?
C4 C9 1.500(4) . ?
C5 C6 1.384(5) . ?
C6 C7 1.389(5) . ?
C6 C8 1.498(5) . ?
C9 C10 1.382(4) . ?
C9 C14 1.401(5) . ?
C10 C11 1.381(5) . ?
C11 C12 1.390(5) . ?
C11 C16 1.502(5) . ?
C12 C13 1.381(5) . ?
C13 C14 1.384(5) . ?
C14 C15 1.531(5) . ?
C15 Co2 2.481(4) 2_646 ?
C16 C17 1.397(4) . ?
C16 C21 1.400(5) . ?
C17 C18 1.392(4) . ?
C18 C19 1.395(5) . ?
C18 C22 1.495(4) . ?
C19 C20 1.382(4) . ?
C20 C21 1.391(4) . ?
C20 C23 1.504(4) . ?
C24 C25A 1.545(14) . ?
C24 C26 1.585(12) . ?
N2 C28 1.596(13) . ?
N2 C29 1.407(11) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Co1 O4 102.45(12) . 1_655 ?
O8 Co1 O1 99.28(15) 4_666 . ?
O8 Co1 O4 99.11(11) 4_666 1_655 ?
O8 Co1 O10 134.58(12) 4_666 3_766 ?
O10 Co1 O1 104.02(12) 3_766 . ?
O10 Co1 O4 112.88(11) 3_766 1_655 ?
O2 Co2 O5 157.45(12) . 2_656 ?
O2 Co2 O6 97.65(13) . 2_656 ?
O2 Co2 O7 94.93(13) . 4_666 ?
O2 Co2 O9 104.31(11) . 3_766 ?
O2 Co2 O11 81.1(2) . . ?
O2 Co2 O11A 102.2(4) . . ?
O2 Co2 C15 127.51(14) . 2_656 ?
O5 Co2 O6 59.83(12) 2_656 2_656 ?
O5 Co2 C15 29.94(13) 2_656 2_656 ?
O6 Co2 C15 29.94(13) 2_656 2_656 ?
O7 Co2 O5 82.92(11) 4_666 2_656 ?
O7 Co2 O6 85.27(13) 4_666 2_656 ?
O7 Co2 C15 81.84(12) 4_666 2_656 ?
O9 Co2 O5 98.24(11) 3_766 2_656 ?
O9 Co2 O6 157.96(12) 3_766 2_656 ?
O9 Co2 O7 94.60(12) 3_766 4_666 ?
O9 Co2 O11 94.7(2) 3_766 . ?
O9 Co2 C15 128.18(13) 3_766 2_656 ?
O11 Co2 O5 97.4(2) . 2_656 ?
O11 Co2 O6 86.7(2) . 2_656 ?
O11 Co2 O7 170.5(2) . 4_666 ?
O11 Co2 C15 93.7(2) . 2_656 ?
O11A Co2 O5 83.8(4) . 2_656 ?
O11A Co2 O6 98.8(3) . 2_656 ?
O11A Co2 O7 161.7(5) . 4_666 ?
O11A Co2 O9 74.9(4) . 3_766 ?
O11A Co2 C15 92.8(3) . 2_656 ?
C1 O1 Co1 116.2(3) . . ?
C1 O2 Co2 159.1(3) . . ?
C8 O4 Co1 99.6(2) . 1_455 ?
C15 O5 Co2 89.2(2) . 2_646 ?
C15 O6 Co2 89.0(2) . 2_646 ?
C23 O7 Co2 131.9(2) . 4_565 ?
C23 O8 Co1 138.3(2) . 4_565 ?
C22 O9 Co2 132.2(2) . 3_766 ?
C22 O10 Co1 117.6(2) . 3_766 ?
C24 O11 Co2 138.2(6) . . ?
C24 O11A Co2 138.8(11) . . ?
C24 N1 C25 113.4(11) . . ?
C24 N1 C27 123.0(11) . . ?
C25 N1 C27 122.2(10) . . ?
C24 N1A C26A 104.7(11) . . ?
C24 N1A C27 130.9(12) . . ?
C27 N1A C26A 124.3(12) . . ?
O1 C1 C2 117.9(3) . . ?
O2 C1 O1 124.5(3) . . ?
O2 C1 C2 117.6(3) . . ?
C3 C2 C1 119.4(3) . . ?
C7 C2 C1 120.7(3) . . ?
C7 C2 C3 119.9(3) . . ?
C2 C3 C4 120.4(3) . . ?
C3 C4 C5 119.0(3) . . ?
C3 C4 C9 119.1(3) . . ?
C5 C4 C9 121.8(3) . . ?
C6 C5 C4 120.7(3) . . ?
C5 C6 C7 119.7(3) . . ?
C5 C6 C8 120.3(3) . . ?
C7 C6 C8 120.0(3) . . ?
C2 C7 C6 120.2(3) . . ?
O3 C8 O4 121.4(3) . . ?
O3 C8 C6 121.1(3) . . ?
O4 C8 C6 117.5(3) . . ?
C10 C9 C4 117.7(3) . . ?
C10 C9 C14 118.6(3) . . ?
C14 C9 C4 123.6(3) . . ?
C11 C10 C9 123.3(3) . . ?
C10 C11 C12 117.1(3) . . ?
C10 C11 C16 120.9(3) . . ?
C12 C11 C16 121.9(3) . . ?
C13 C12 C11 121.0(4) . . ?
C12 C13 C14 121.1(4) . . ?
C9 C14 C15 123.4(3) . . ?
C13 C14 C9 118.9(3) . . ?
C13 C14 C15 117.7(3) . . ?
O5 C15 Co2 60.86(19) . 2_646 ?
O5 C15 C14 120.2(4) . . ?
O6 C15 Co2 61.11(19) . 2_646 ?
O6 C15 O5 121.8(3) . . ?
O6 C15 C14 118.0(4) . . ?
C14 C15 Co2 175.2(3) . 2_646 ?
C17 C16 C11 120.7(3) . . ?
C17 C16 C21 117.8(3) . . ?
C21 C16 C11 121.4(3) . . ?
C18 C17 C16 121.9(3) . . ?
C17 C18 C19 118.7(3) . . ?
C17 C18 C22 121.3(3) . . ?
C19 C18 C22 119.8(3) . . ?
C20 C19 C18 120.6(3) . . ?
C19 C20 C21 119.9(3) . . ?
C19 C20 C23 119.1(3) . . ?
C21 C20 C23 120.9(3) . . ?
C20 C21 C16 121.0(3) . . ?
O9 C22 O10 124.4(3) . . ?
O9 C22 C18 119.1(3) . . ?
O10 C22 C18 116.4(3) . . ?
O7 C23 O8 126.1(3) . . ?
O7 C23 C20 118.8(3) . . ?
O8 C23 C20 115.1(3) . . ?
O11 C24 N1 128.5(9) . . ?
O11 C24 C26 113.6(6) . . ?
O11A C24 N1A 127.3(11) . . ?
O11A C24 C25A 121.1(11) . . ?
N1 C24 C26 116.2(8) . . ?
N1A C24 C25A 110.4(11) . . ?
C29 N2 C28 112.0(10) . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3_sq
_audit_block_doi                 10.5517/ccdc.csd.cc1lj65h
_database_code_depnum_ccdc_archive 'CCDC 1475326'
_audit_update_record             
;
2016-08-23 deposited with the CCDC.
2016-08-26 downloaded from the CCDC.
;
_audit_creation_date             2016-08-23
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.08.19 svn.r3327 for OlexSys, GUI svn.r5215)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H11 Co2 O11, C2 H8 N'
_chemical_formula_sum            'C25 H19 Co2 N O11'
_chemical_formula_weight         627.27
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.230(3)
_cell_length_b                   9.468(3)
_cell_length_c                   28.006(9)
_cell_angle_alpha                90
_cell_angle_beta                 98.048(6)
_cell_angle_gamma                90
_cell_volume                     2685.8(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2575
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      24.390
_cell_measurement_theta_min      2.945
_shelx_estimated_absorpt_T_max   0.871
_shelx_estimated_absorpt_T_min   0.829
_exptl_absorpt_coefficient_mu    1.295
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6421
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0740 before and 0.0616 after correction.
The Ratio of minimum to maximum transmission is 0.8611.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.551
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1272
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0644
_diffrn_reflns_av_unetI/netI     0.0814
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            13919
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.677
_diffrn_reflns_theta_min         1.469
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3992
_reflns_number_total             5101
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         1.775
_refine_diff_density_min         -0.898
_refine_diff_density_rms         0.234
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     355
_refine_ls_number_reflns         5101
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.1186
_refine_ls_R_factor_gt           0.0941
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1926P)²+25.5291P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2758
_refine_ls_wR_factor_ref         0.3105
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.908(2) 0.092(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
3. Uiso/Uaniso restraints and constraints
Uanis(C12) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.04
4. Rigid body (RIGU) restrains
 N1, C24, C25
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O11
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5.a Riding coordinates:
 O11(H11A,H11B)
5.b Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B)
5.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C7(H7), C11(H11), C12(H12), C14(H14), C17(H17), C19(H19),
 C21(H21)
5.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C25(H25A,H25B,H25C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.77973(12) 1.38336(14) 0.69352(4) 0.0176(4) Uani 1 1 d . . . . .
Co2 Co 0.55644(12) 1.43970(15) 0.59720(4) 0.0186(4) Uani 1 1 d . . . . .
O1 O 0.5327(8) 1.2463(8) 0.6264(3) 0.040(2) Uani 1 1 d . . . . .
O11 O 0.5785(9) 1.6409(10) 0.5642(3) 0.043(2) Uani 1 1 d . U . . .
H11A H 0.5015 1.6514 0.5694 0.065 Uiso 1 1 d R . . . .
H11B H 0.5886 1.6337 0.5347 0.065 Uiso 1 1 d R . . . .
O2 O 0.7099(7) 1.1869(8) 0.6778(3) 0.0284(17) Uani 1 1 d . . . . .
O3 O 0.7825(7) 0.6527(8) 0.7059(3) 0.0275(16) Uani 1 1 d . . . . .
O4 O 0.6326(7) 0.5183(7) 0.6660(2) 0.0221(15) Uani 1 1 d . . . . .
O5 O 0.2877(8) 0.8780(10) 0.7350(3) 0.037(2) Uani 1 1 d . . . . .
O6 O 0.0812(7) 0.8486(9) 0.7452(2) 0.0296(18) Uani 1 1 d . . . . .
O7 O -0.4103(7) 0.6259(10) 0.4642(3) 0.0349(19) Uani 1 1 d . . . . .
O8 O -0.3479(6) 0.5388(8) 0.3992(2) 0.0205(15) Uani 1 1 d . . . . .
O9 O 0.1006(7) 0.6078(9) 0.3590(2) 0.0278(17) Uani 1 1 d . . . . .
O10 O 0.2626(7) 0.6108(10) 0.4219(3) 0.0341(19) Uani 1 1 d . . . . .
C1 C 0.6030(10) 1.1590(11) 0.6520(4) 0.022(2) Uani 1 1 d . . . . .
C2 C 0.5518(9) 1.0101(10) 0.6533(4) 0.0191(19) Uani 1 1 d . . . . .
C3 C 0.6357(10) 0.8988(11) 0.6678(4) 0.024(2) Uani 1 1 d . . . . .
H3 H 0.7255 0.9144 0.6770 0.029 Uiso 1 1 calc R . . . .
C4 C 0.5837(10) 0.7629(11) 0.6687(3) 0.021(2) Uani 1 1 d . . . . .
C5 C 0.4491(10) 0.7417(11) 0.6579(3) 0.020(2) Uani 1 1 d . . . . .
H5 H 0.4149 0.6513 0.6601 0.024 Uiso 1 1 calc R . . . .
C6 C 0.3639(9) 0.8537(11) 0.6437(4) 0.020(2) Uani 1 1 d . . . . .
C7 C 0.4157(10) 0.9846(12) 0.6403(4) 0.024(2) Uani 1 1 d . . . . .
H7 H 0.3603 1.0591 0.6293 0.029 Uiso 1 1 calc R . . . .
C8 C 0.6739(10) 0.6395(10) 0.6811(3) 0.020(2) Uani 1 1 d . . . . .
C9 C 0.2190(9) 0.8246(11) 0.6314(4) 0.021(2) Uani 1 1 d . . . . .
C10 C 0.1307(10) 0.8252(11) 0.6649(3) 0.021(2) Uani 1 1 d . . . . .
C11 C -0.0018(10) 0.7915(14) 0.6487(3) 0.029(3) Uani 1 1 d . . . . .
H11 H -0.0611 0.7926 0.6710 0.035 Uiso 1 1 calc R . . . .
C12 C -0.0497(10) 0.7563(15) 0.6008(4) 0.033(3) Uani 1 1 d . U . . .
H12 H -0.1380 0.7331 0.5916 0.039 Uiso 1 1 calc R . . . .
C13 C 0.0392(9) 0.7572(11) 0.5674(3) 0.021(2) Uani 1 1 d . . . . .
C14 C 0.1692(9) 0.7928(12) 0.5838(3) 0.023(2) Uani 1 1 d . . . . .
H14 H 0.2278 0.7956 0.5612 0.027 Uiso 1 1 calc R . . . .
C15 C 0.1712(10) 0.8528(11) 0.7180(3) 0.022(2) Uani 1 1 d . . . . .
C16 C -0.0052(9) 0.7130(12) 0.5166(4) 0.025(2) Uani 1 1 d . . . . .
C17 C -0.1377(10) 0.6819(12) 0.5005(4) 0.025(2) Uani 1 1 d . . . . .
H17 H -0.2000 0.6965 0.5212 0.031 Uiso 1 1 calc R . . . .
C18 C -0.1779(10) 0.6308(11) 0.4553(3) 0.021(2) Uani 1 1 d . . . . .
C19 C -0.0875(9) 0.6087(11) 0.4232(3) 0.019(2) Uani 1 1 d . . . . .
H19 H -0.1157 0.5726 0.3926 0.023 Uiso 1 1 calc R . . . .
C20 C 0.0444(10) 0.6405(12) 0.4370(3) 0.022(2) Uani 1 1 d . . . . .
C21 C 0.0849(9) 0.6890(11) 0.4844(4) 0.022(2) Uani 1 1 d . . . . .
H21 H 0.1741 0.7055 0.4944 0.027 Uiso 1 1 calc R . . . .
C22 C 0.1466(10) 0.6159(11) 0.4042(4) 0.024(2) Uani 1 1 d . . . . .
C23 C -0.3209(10) 0.5951(11) 0.4379(4) 0.024(2) Uani 1 1 d . . . . .
N1 N 0.8425(14) 0.8419(14) 0.7891(4) 0.053(3) Uani 1 1 d . U . . .
H1A H 0.8585 0.8078 0.7609 0.064 Uiso 1 1 calc R . . . .
H1B H 0.9151 0.8307 0.8103 0.064 Uiso 1 1 calc R . . . .
C24 C 0.812(2) 0.989(2) 0.7841(7) 0.076(5) Uani 1 1 d . U . . .
H24A H 0.7813 1.0228 0.8130 0.114 Uiso 1 1 calc GR . . . .
H24B H 0.7444 1.0030 0.7571 0.114 Uiso 1 1 calc GR . . . .
H24C H 0.8898 1.0404 0.7790 0.114 Uiso 1 1 calc GR . . . .
C25 C 0.737(3) 0.764(3) 0.8049(8) 0.106(8) Uani 1 1 d . U . . .
H25A H 0.6560 0.7841 0.7840 0.159 Uiso 1 1 calc GR . . . .
H25B H 0.7273 0.7916 0.8373 0.159 Uiso 1 1 calc GR . . . .
H25C H 0.7552 0.6650 0.8041 0.159 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 O2 2.018(7) . ?
Co1 O4 2.042(7) 1_565 ?
Co1 O5 2.207(7) 2_656 ?
Co1 O6 2.095(7) 2_656 ?
Co1 O9 2.042(7) 3_676 ?
Co1 C15 2.476(9) 2_656 ?
Co2 O1 2.033(8) . ?
Co2 O11 2.142(9) . ?
Co2 O4 2.110(7) 1_565 ?
Co2 O7 2.204(8) 3_576 ?
Co2 O8 2.159(6) 3_576 ?
Co2 O10 2.054(7) 3_676 ?
Co2 C23 2.494(10) 3_576 ?
O1 C1 1.253(13) . ?
O11 H11A 0.8260 . ?
O11 H11B 0.8493 . ?
O2 C1 1.252(13) . ?
O3 C8 1.231(12) . ?
O4 Co1 2.042(7) 1_545 ?
O4 Co2 2.110(7) 1_545 ?
O4 C8 1.275(13) . ?
O5 Co1 2.207(7) 2_646 ?
O5 C15 1.243(13) . ?
O6 Co1 2.095(7) 2_646 ?
O6 C15 1.276(13) . ?
O7 Co2 2.204(8) 3_576 ?
O7 C23 1.285(13) . ?
O8 Co2 2.159(6) 3_576 ?
O8 C23 1.205(13) . ?
O9 Co1 2.042(7) 3_676 ?
O9 C22 1.289(12) . ?
O10 Co2 2.054(7) 3_676 ?
O10 C22 1.222(13) . ?
C1 C2 1.506(14) . ?
C2 C3 1.384(14) . ?
C2 C7 1.410(13) . ?
C3 H3 0.9300 . ?
C3 C4 1.394(15) . ?
C4 C5 1.382(14) . ?
C4 C8 1.499(14) . ?
C5 H5 0.9300 . ?
C5 C6 1.395(14) . ?
C6 C7 1.356(15) . ?
C6 C9 1.500(13) . ?
C7 H7 0.9300 . ?
C9 C10 1.390(14) . ?
C9 C14 1.393(13) . ?
C10 C11 1.405(14) . ?
C10 C15 1.510(13) . ?
C11 H11 0.9300 . ?
C11 C12 1.402(14) . ?
C12 H12 0.9300 . ?
C12 C13 1.394(14) . ?
C13 C14 1.387(13) . ?
C13 C16 1.491(14) . ?
C14 H14 0.9300 . ?
C15 Co1 2.476(9) 2_646 ?
C16 C17 1.398(14) . ?
C16 C21 1.396(14) . ?
C17 H17 0.9300 . ?
C17 C18 1.366(14) . ?
C18 C19 1.392(14) . ?
C18 C23 1.513(13) . ?
C19 H19 0.9300 . ?
C19 C20 1.384(14) . ?
C20 C21 1.410(14) . ?
C20 C22 1.504(14) . ?
C21 H21 0.9300 . ?
C23 Co2 2.494(10) 3_576 ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 C24 1.43(2) . ?
N1 C25 1.43(2) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Co1 O4 105.9(3) . 1_565 ?
O2 Co1 O5 91.7(4) . 2_656 ?
O2 Co1 O6 102.3(3) . 2_656 ?
O2 Co1 O9 96.3(3) . 3_676 ?
O2 Co1 C15 97.3(3) . 2_656 ?
O4 Co1 O5 92.8(3) 1_565 2_656 ?
O4 Co1 O6 142.0(3) 1_565 2_656 ?
O4 Co1 O9 100.8(3) 1_565 3_676 ?
O4 Co1 C15 119.1(3) 1_565 2_656 ?
O5 Co1 C15 30.1(3) 2_656 2_656 ?
O6 Co1 O5 61.1(3) 2_656 2_656 ?
O6 Co1 C15 31.0(3) 2_656 2_656 ?
O9 Co1 O5 161.6(3) 3_676 2_656 ?
O9 Co1 O6 100.9(3) 3_676 2_656 ?
O9 Co1 C15 131.9(3) 3_676 2_656 ?
O1 Co2 O11 178.1(4) . . ?
O1 Co2 O4 90.0(3) . 1_565 ?
O1 Co2 O7 87.3(3) . 3_576 ?
O1 Co2 O8 83.8(3) . 3_576 ?
O1 Co2 O10 93.3(4) . 3_676 ?
O1 Co2 C23 82.9(3) . 3_576 ?
O11 Co2 O7 90.9(3) . 3_576 ?
O11 Co2 O8 95.8(3) . 3_576 ?
O11 Co2 C23 95.8(3) . 3_576 ?
O4 Co2 O11 91.9(3) 1_565 . ?
O4 Co2 O7 159.2(3) 1_565 3_576 ?
O4 Co2 O8 99.5(3) 1_565 3_576 ?
O4 Co2 C23 128.3(3) 1_565 3_576 ?
O7 Co2 C23 31.0(3) 3_576 3_576 ?
O8 Co2 O7 59.7(3) 3_576 3_576 ?
O8 Co2 C23 28.9(3) 3_576 3_576 ?
O10 Co2 O11 86.7(4) 3_676 . ?
O10 Co2 O4 95.1(3) 3_676 1_565 ?
O10 Co2 O7 105.6(3) 3_676 3_576 ?
O10 Co2 O8 165.1(3) 3_676 3_576 ?
O10 Co2 C23 136.3(4) 3_676 3_576 ?
C1 O1 Co2 137.1(7) . . ?
Co2 O11 H11A 82.6 . . ?
Co2 O11 H11B 112.5 . . ?
H11A O11 H11B 115.4 . . ?
C1 O2 Co1 125.1(7) . . ?
Co1 O4 Co2 106.4(3) 1_545 1_545 ?
C8 O4 Co1 104.2(6) . 1_545 ?
C8 O4 Co2 133.2(6) . 1_545 ?
C15 O5 Co1 87.0(6) . 2_646 ?
C15 O6 Co1 91.2(6) . 2_646 ?
C23 O7 Co2 87.1(6) . 3_576 ?
C23 O8 Co2 91.2(6) . 3_576 ?
C22 O9 Co1 122.1(6) . 3_676 ?
C22 O10 Co2 139.7(7) . 3_676 ?
O1 C1 C2 117.2(9) . . ?
O2 C1 O1 125.2(10) . . ?
O2 C1 C2 117.5(9) . . ?
C3 C2 C1 121.1(9) . . ?
C3 C2 C7 119.7(9) . . ?
C7 C2 C1 119.2(9) . . ?
C2 C3 H3 120.5 . . ?
C2 C3 C4 119.0(9) . . ?
C4 C3 H3 120.5 . . ?
C3 C4 C8 119.9(9) . . ?
C5 C4 C3 120.1(9) . . ?
C5 C4 C8 120.0(9) . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 121.0(9) . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C9 118.9(9) . . ?
C7 C6 C5 118.7(9) . . ?
C7 C6 C9 122.3(9) . . ?
C2 C7 H7 119.3 . . ?
C6 C7 C2 121.3(10) . . ?
C6 C7 H7 119.3 . . ?
O3 C8 O4 120.7(9) . . ?
O3 C8 C4 121.9(9) . . ?
O4 C8 C4 117.3(9) . . ?
C10 C9 C6 124.0(9) . . ?
C10 C9 C14 117.6(9) . . ?
C14 C9 C6 118.4(8) . . ?
C9 C10 C11 118.0(9) . . ?
C9 C10 C15 123.5(9) . . ?
C11 C10 C15 118.5(9) . . ?
C10 C11 H11 118.1 . . ?
C12 C11 C10 123.8(9) . . ?
C12 C11 H11 118.1 . . ?
C11 C12 H12 121.1 . . ?
C13 C12 C11 117.8(9) . . ?
C13 C12 H12 121.1 . . ?
C12 C13 C16 119.9(9) . . ?
C14 C13 C12 117.7(9) . . ?
C14 C13 C16 122.3(9) . . ?
C9 C14 H14 117.5 . . ?
C13 C14 C9 125.1(9) . . ?
C13 C14 H14 117.5 . . ?
O5 C15 Co1 62.9(5) . 2_646 ?
O5 C15 O6 120.6(9) . . ?
O5 C15 C10 121.8(9) . . ?
O6 C15 Co1 57.8(5) . 2_646 ?
O6 C15 C10 117.5(8) . . ?
C10 C15 Co1 174.6(7) . 2_646 ?
C17 C16 C13 121.2(9) . . ?
C21 C16 C13 121.4(9) . . ?
C21 C16 C17 117.1(9) . . ?
C16 C17 H17 119.1 . . ?
C18 C17 C16 121.7(9) . . ?
C18 C17 H17 119.1 . . ?
C17 C18 C19 120.7(9) . . ?
C17 C18 C23 121.9(9) . . ?
C19 C18 C23 117.4(9) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 C18 119.8(9) . . ?
C20 C19 H19 120.1 . . ?
C19 C20 C21 118.7(9) . . ?
C19 C20 C22 121.9(9) . . ?
C21 C20 C22 119.2(9) . . ?
C16 C21 C20 121.8(9) . . ?
C16 C21 H21 119.1 . . ?
C20 C21 H21 119.1 . . ?
O9 C22 C20 114.9(9) . . ?
O10 C22 O9 126.7(10) . . ?
O10 C22 C20 118.4(9) . . ?
O7 C23 Co2 62.0(5) . 3_576 ?
O7 C23 C18 119.9(9) . . ?
O8 C23 Co2 59.9(5) . 3_576 ?
O8 C23 O7 121.5(9) . . ?
O8 C23 C18 118.5(9) . . ?
C18 C23 Co2 173.3(7) . 3_576 ?
H1A N1 H1B 108.0 . . ?
C24 N1 H1A 109.3 . . ?
C24 N1 H1B 109.3 . . ?
C25 N1 H1A 109.3 . . ?
C25 N1 H1B 109.3 . . ?
C25 N1 C24 111.5(18) . . ?
N1 C24 H24A 109.5 . . ?
N1 C24 H24B 109.5 . . ?
N1 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N1 C25 H25A 109.5 . . ?
N1 C25 H25B 109.5 . . ?
N1 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 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
Co1 O2 C1 O1 11.0(16) . . . . ?
Co1 O2 C1 C2 -166.3(7) . . . . ?
Co1 O4 C8 O3 1.1(11) 1_545 . . . ?
Co1 O4 C8 C4 -177.3(7) 1_545 . . . ?
Co1 O5 C15 O6 2.6(11) 2_646 . . . ?
Co1 O5 C15 C10 -177.0(9) 2_646 . . . ?
Co1 O6 C15 O5 -2.7(11) 2_646 . . . ?
Co1 O6 C15 C10 176.9(8) 2_646 . . . ?
Co1 O9 C22 O10 -10.3(16) 3_676 . . . ?
Co1 O9 C22 C20 166.8(7) 3_676 . . . ?
Co2 O1 C1 O2 19.6(19) . . . . ?
Co2 O1 C1 C2 -163.0(8) . . . . ?
Co2 O4 C8 O3 -128.5(9) 1_545 . . . ?
Co2 O4 C8 C4 53.2(12) 1_545 . . . ?
Co2 O7 C23 O8 -6.8(10) 3_576 . . . ?
Co2 O7 C23 C18 172.6(9) 3_576 . . . ?
Co2 O8 C23 O7 6.9(11) 3_576 . . . ?
Co2 O8 C23 C18 -172.5(8) 3_576 . . . ?
Co2 O10 C22 O9 -12(2) 3_676 . . . ?
Co2 O10 C22 C20 170.6(8) 3_676 . . . ?
O1 C1 C2 C3 160.4(10) . . . . ?
O1 C1 C2 C7 -20.9(15) . . . . ?
O2 C1 C2 C3 -22.0(15) . . . . ?
O2 C1 C2 C7 156.6(10) . . . . ?
C1 C2 C3 C4 179.7(9) . . . . ?
C1 C2 C7 C6 -176.1(9) . . . . ?
C2 C3 C4 C5 -3.9(15) . . . . ?
C2 C3 C4 C8 175.9(9) . . . . ?
C3 C2 C7 C6 2.6(15) . . . . ?
C3 C4 C5 C6 3.2(15) . . . . ?
C3 C4 C8 O3 25.2(14) . . . . ?
C3 C4 C8 O4 -156.5(9) . . . . ?
C4 C5 C6 C7 0.4(15) . . . . ?
C4 C5 C6 C9 178.8(9) . . . . ?
C5 C4 C8 O3 -155.1(10) . . . . ?
C5 C4 C8 O4 23.2(13) . . . . ?
C5 C6 C7 C2 -3.3(15) . . . . ?
C5 C6 C9 C10 88.3(13) . . . . ?
C5 C6 C9 C14 -90.6(13) . . . . ?
C6 C9 C10 C11 -177.9(11) . . . . ?
C6 C9 C10 C15 -1.2(17) . . . . ?
C6 C9 C14 C13 176.8(10) . . . . ?
C7 C2 C3 C4 1.0(15) . . . . ?
C7 C6 C9 C10 -93.3(14) . . . . ?
C7 C6 C9 C14 87.8(13) . . . . ?
C8 C4 C5 C6 -176.5(9) . . . . ?
C9 C6 C7 C2 178.3(9) . . . . ?
C9 C10 C11 C12 0.5(19) . . . . ?
C9 C10 C15 O5 0.6(17) . . . . ?
C9 C10 C15 O6 -179.1(10) . . . . ?
C10 C9 C14 C13 -2.1(18) . . . . ?
C10 C11 C12 C13 -1(2) . . . . ?
C11 C10 C15 O5 177.3(11) . . . . ?
C11 C10 C15 O6 -2.4(16) . . . . ?
C11 C12 C13 C14 0.1(18) . . . . ?
C11 C12 C13 C16 176.7(11) . . . . ?
C12 C13 C14 C9 1.6(18) . . . . ?
C12 C13 C16 C17 5.5(17) . . . . ?
C12 C13 C16 C21 -168.7(11) . . . . ?
C13 C16 C17 C18 -174.7(10) . . . . ?
C13 C16 C21 C20 176.8(10) . . . . ?
C14 C9 C10 C11 1.0(16) . . . . ?
C14 C9 C10 C15 177.8(10) . . . . ?
C14 C13 C16 C17 -177.9(11) . . . . ?
C14 C13 C16 C21 7.8(17) . . . . ?
C15 C10 C11 C12 -176.4(12) . . . . ?
C16 C13 C14 C9 -175.0(11) . . . . ?
C16 C17 C18 C19 -0.5(17) . . . . ?
C16 C17 C18 C23 179.1(10) . . . . ?
C17 C16 C21 C20 2.3(17) . . . . ?
C17 C18 C19 C20 -0.8(16) . . . . ?
C17 C18 C23 O7 7.0(16) . . . . ?
C17 C18 C23 O8 -173.5(10) . . . . ?
C18 C19 C20 C21 2.8(16) . . . . ?
C18 C19 C20 C22 178.8(10) . . . . ?
C19 C18 C23 O7 -173.3(10) . . . . ?
C19 C18 C23 O8 6.1(15) . . . . ?
C19 C20 C21 C16 -3.6(17) . . . . ?
C19 C20 C22 O9 21.3(15) . . . . ?
C19 C20 C22 O10 -161.3(10) . . . . ?
C21 C16 C17 C18 -0.2(17) . . . . ?
C21 C20 C22 O9 -162.8(10) . . . . ?
C21 C20 C22 O10 14.6(15) . . . . ?
C22 C20 C21 C16 -179.7(10) . . . . ?
C23 C18 C19 C20 179.5(9) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.908(2)
2 0.092(2)

####################################################################### 
# 
# 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_4_sq
_audit_block_doi                 10.5517/ccdc.csd.cc1lj66j
_database_code_depnum_ccdc_archive 'CCDC 1475327'
_audit_update_record             
;
2016-08-23 deposited with the CCDC.
2016-08-26 downloaded from the CCDC.
;
_audit_creation_date             2016-08-23
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.08.19 svn.r3327 for OlexSys, GUI svn.r5215)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H18 Mn2 N O12, C2 H8 N'
_chemical_formula_sum            'C28 H26 Mn2 N2 O12'
_chemical_formula_weight         692.39
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.6150(16)
_cell_length_b                   9.6419(14)
_cell_length_c                   28.480(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.819(3)
_cell_angle_gamma                90
_cell_volume                     2904.6(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4209
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      27.806
_cell_measurement_theta_min      2.554
_shelx_estimated_absorpt_T_max   0.827
_shelx_estimated_absorpt_T_min   0.786
_exptl_absorpt_coefficient_mu    0.937
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6510
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0803 before and 0.0539 after correction.
The Ratio of minimum to maximum transmission is 0.8730.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.583
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1416
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_av_unetI/netI     0.0511
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            15081
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         1.925
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4547
_reflns_number_total             5652
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.836
_refine_diff_density_min         -0.468
_refine_diff_density_rms         0.097
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         5652
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0441
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0713P)²+2.2778P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1212
_refine_ls_wR_factor_ref         0.1316
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Riding coordinates:
 O1W(H1WA,H1WB)
2.b Secondary CH2 refined with riding coordinates:
 N2(H2A,H2B)
2.c Me refined with riding coordinates:
 C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C28(H28A,H28B,
 H28C)
2.d Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C7(H7), C10(H10), C13(H13), C14(H14), C16(H16), C18(H18),
 C20(H20), C24(H24)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 1.55212(4) 0.19468(5) 1.09425(2) 0.01863(14) Uani 1 1 d . . . . .
Mn2 Mn 0.76770(4) 0.26041(5) 0.69087(2) 0.01722(14) Uani 1 1 d . . . . .
O1 O 1.35143(19) 0.1487(2) 1.09054(7) 0.0234(5) Uani 1 1 d . . . . .
O1W O 1.5864(2) -0.0066(2) 1.06123(8) 0.0265(5) Uani 1 1 d . . . . .
H1WA H 1.6566 0.0015 1.0423 0.040 Uiso 1 1 d R . . . .
H1WB H 1.5124 -0.0338 1.0417 0.040 Uiso 1 1 d R . . . .
O2 O 1.3438(2) 0.0051(3) 1.02878(8) 0.0291(5) Uani 1 1 d . . . . .
O3 O 0.9044(2) 0.2153(3) 1.14198(8) 0.0291(5) Uani 1 1 d . . . . .
O4 O 0.7484(2) 0.2343(3) 1.08571(8) 0.0309(6) Uani 1 1 d . . . . .
O5 O 0.4728(2) 0.6201(2) 0.86720(9) 0.0328(6) Uani 1 1 d . . . . .
O6 O 0.2975(2) 0.5557(2) 0.82418(8) 0.0312(5) Uani 1 1 d . . . . .
O7 O 0.3877(2) -0.1042(2) 0.83569(7) 0.0211(5) Uani 1 1 d . . . . .
O8 O 0.2414(2) 0.0299(2) 0.80041(8) 0.0313(6) Uani 1 1 d . . . . .
O9 O 0.9107(2) 0.2099(3) 0.75057(8) 0.0419(7) Uani 1 1 d . . . . .
O10 O 0.7190(2) 0.2571(3) 0.76477(8) 0.0423(7) Uani 1 1 d . . . . .
O11 O 1.5167(3) 0.2961(3) 1.02548(10) 0.0468(7) Uani 1 1 d . . . . .
N1 N 1.3391(3) 0.3993(3) 0.99237(10) 0.0354(7) Uani 1 1 d . . . . .
C1 C 1.2951(3) 0.0922(3) 1.05434(10) 0.0203(6) Uani 1 1 d . . . . .
C2 C 1.1609(3) 0.1344(3) 1.04084(10) 0.0194(6) Uani 1 1 d . . . . .
C3 C 1.0792(3) 0.1648(3) 1.07546(10) 0.0207(6) Uani 1 1 d . . . . .
H3 H 1.1089 0.1636 1.1071 0.025 Uiso 1 1 calc R . . . .
C4 C 0.9540(3) 0.1967(3) 1.06252(10) 0.0193(6) Uani 1 1 d . . . . .
C5 C 0.9118(3) 0.2053(3) 1.01461(10) 0.0206(6) Uani 1 1 d . . . . .
H5 H 0.8281 0.2293 1.0061 0.025 Uiso 1 1 calc R . . . .
C6 C 0.9916(3) 0.1790(3) 0.97957(10) 0.0201(6) Uani 1 1 d . . . . .
C7 C 1.1164(3) 0.1396(3) 0.99386(10) 0.0214(6) Uani 1 1 d . . . . .
H7 H 1.1706 0.1164 0.9711 0.026 Uiso 1 1 calc R . . . .
C8 C 0.8619(3) 0.2171(3) 1.09947(11) 0.0210(6) Uani 1 1 d . . . . .
C9 C 0.9487(3) 0.1879(3) 0.92823(10) 0.0204(6) Uani 1 1 d . . . . .
C10 C 0.8212(3) 0.2082(3) 0.91309(10) 0.0189(6) Uani 1 1 d . . . . .
H10 H 0.7632 0.2169 0.9356 0.023 Uiso 1 1 calc R . . . .
C11 C 0.7773(3) 0.2159(3) 0.86545(10) 0.0170(6) Uani 1 1 d . . . . .
C12 C 0.8642(3) 0.2062(3) 0.83139(11) 0.0227(7) Uani 1 1 d . . . . .
C13 C 0.9914(3) 0.1830(4) 0.84621(11) 0.0309(8) Uani 1 1 d . . . . .
H13 H 1.0495 0.1735 0.8237 0.037 Uiso 1 1 calc R . . . .
C14 C 1.0326(3) 0.1741(4) 0.89301(11) 0.0302(8) Uani 1 1 d . . . . .
H14 H 1.1179 0.1585 0.9016 0.036 Uiso 1 1 calc R . . . .
C15 C 0.6379(3) 0.2343(3) 0.85398(10) 0.0165(6) Uani 1 1 d . . . . .
C16 C 0.5846(3) 0.3659(3) 0.85524(10) 0.0191(6) Uani 1 1 d . . . . .
H16 H 0.6361 0.4417 0.8634 0.023 Uiso 1 1 calc R . . . .
C17 C 0.4548(3) 0.3865(3) 0.84440(10) 0.0189(6) Uani 1 1 d . . . . .
C18 C 0.3779(3) 0.2723(3) 0.83303(11) 0.0204(6) Uani 1 1 d . . . . .
H18 H 0.2919 0.2848 0.8251 0.025 Uiso 1 1 calc R . . . .
C19 C 0.4296(3) 0.1397(3) 0.83356(10) 0.0189(6) Uani 1 1 d . . . . .
C20 C 0.5594(3) 0.1215(3) 0.84351(10) 0.0193(6) Uani 1 1 d . . . . .
H20 H 0.5937 0.0328 0.8431 0.023 Uiso 1 1 calc R . . . .
C21 C 0.4038(3) 0.5314(3) 0.84537(11) 0.0215(6) Uani 1 1 d . . . . .
C22 C 0.3469(3) 0.0157(3) 0.82223(10) 0.0185(6) Uani 1 1 d . . . . .
C23 C 0.8287(3) 0.2247(3) 0.77952(11) 0.0229(7) Uani 1 1 d . . . . .
C24 C 1.4417(4) 0.3225(4) 0.99136(14) 0.0383(9) Uani 1 1 d . . . . .
H24 H 1.4588 0.2853 0.9624 0.046 Uiso 1 1 calc R . . . .
C25 C 1.3069(5) 0.4647(5) 1.03562(16) 0.0560(12) Uani 1 1 d . . . . .
H25A H 1.2297 0.5160 1.0297 0.084 Uiso 1 1 calc R . . . .
H25B H 1.2960 0.3948 1.0589 0.084 Uiso 1 1 calc R . . . .
H25C H 1.3736 0.5265 1.0469 0.084 Uiso 1 1 calc R . . . .
C26 C 1.2607(4) 0.4307(5) 0.94911(16) 0.0580(12) Uani 1 1 d . . . . .
H26A H 1.1905 0.4873 0.9564 0.087 Uiso 1 1 calc R . . . .
H26B H 1.3102 0.4796 0.9277 0.087 Uiso 1 1 calc R . . . .
H26C H 1.2298 0.3458 0.9347 0.087 Uiso 1 1 calc R . . . .
N2 N 0.1667(5) 0.2066(5) 0.72487(15) 0.0700(12) Uani 1 1 d . . . . .
H2A H 0.0966 0.1920 0.7392 0.084 Uiso 1 1 calc R . . . .
H2B H 0.2308 0.1805 0.7451 0.084 Uiso 1 1 calc R . . . .
C27 C 0.1632(9) 0.1083(9) 0.6862(2) 0.136(4) Uani 1 1 d . . . . .
H27A H 0.1556 0.0159 0.6983 0.204 Uiso 1 1 calc R . . . .
H27B H 0.0920 0.1282 0.6642 0.204 Uiso 1 1 calc R . . . .
H27C H 0.2397 0.1156 0.6707 0.204 Uiso 1 1 calc R . . . .
C28 C 0.1777(8) 0.3556(7) 0.7203(3) 0.122(3) Uani 1 1 d . . . . .
H28A H 0.1780 0.3979 0.7508 0.184 Uiso 1 1 calc R . . . .
H28B H 0.2551 0.3775 0.7067 0.184 Uiso 1 1 calc R . . . .
H28C H 0.1074 0.3901 0.7002 0.184 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mn1 O1 2.170(2) . ?
Mn1 O1W 2.200(2) . ?
Mn1 O4 2.152(2) 1_655 ?
Mn1 O5 2.125(2) 3_767 ?
Mn1 O7 2.221(2) 3_757 ?
Mn1 O11 2.193(3) . ?
Mn2 O3 2.107(2) 4_565 ?
Mn2 O6 2.123(2) 2_646 ?
Mn2 O7 2.188(2) 2_656 ?
Mn2 O9 2.236(2) . ?
Mn2 O10 2.209(2) . ?
O1 C1 1.271(4) . ?
O1W H1WA 0.9601 . ?
O1W H1WB 0.9600 . ?
O2 C1 1.251(4) . ?
O3 Mn2 2.107(2) 4_566 ?
O3 C8 1.256(4) . ?
O4 Mn1 2.152(2) 1_455 ?
O4 C8 1.246(4) . ?
O5 Mn1 2.125(2) 3_767 ?
O5 C21 1.255(4) . ?
O6 Mn2 2.123(2) 2_656 ?
O6 C21 1.256(4) . ?
O7 Mn1 2.222(2) 3_757 ?
O7 Mn2 2.188(2) 2_646 ?
O7 C22 1.282(4) . ?
O8 C22 1.242(4) . ?
O9 C23 1.256(4) . ?
O10 C23 1.244(4) . ?
O11 C24 1.230(4) . ?
N1 C24 1.320(5) . ?
N1 C25 1.450(5) . ?
N1 C26 1.459(5) . ?
C1 C2 1.500(4) . ?
C2 C3 1.398(4) . ?
C2 C7 1.382(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.384(4) . ?
C4 C5 1.403(4) . ?
C4 C8 1.508(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.386(4) . ?
C6 C7 1.405(4) . ?
C6 C9 1.497(4) . ?
C7 H7 0.9300 . ?
C9 C10 1.399(4) . ?
C9 C14 1.403(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.399(4) . ?
C11 C12 1.397(4) . ?
C11 C15 1.499(4) . ?
C12 C13 1.398(4) . ?
C12 C23 1.504(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.370(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.392(4) . ?
C15 C20 1.388(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.400(4) . ?
C17 C18 1.393(4) . ?
C17 C21 1.499(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.391(4) . ?
C19 C20 1.395(4) . ?
C19 C22 1.502(4) . ?
C20 H20 0.9300 . ?
C24 H24 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 C27 1.450(8) . ?
N2 C28 1.448(8) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Mn1 O1W 89.77(9) . . ?
O1 Mn1 O7 99.83(8) . 3_757 ?
O1 Mn1 O11 87.32(9) . . ?
O1W Mn1 O7 89.55(8) . 3_757 ?
O4 Mn1 O1 170.62(9) 1_655 . ?
O4 Mn1 O1W 84.93(9) 1_655 . ?
O4 Mn1 O7 87.88(9) 1_655 3_757 ?
O4 Mn1 O11 85.14(10) 1_655 . ?
O5 Mn1 O1 91.87(9) 3_767 . ?
O5 Mn1 O1W 174.06(9) 3_767 . ?
O5 Mn1 O4 94.18(10) 3_767 1_655 ?
O5 Mn1 O7 84.55(9) 3_767 3_757 ?
O5 Mn1 O11 93.86(11) 3_767 . ?
O11 Mn1 O1W 91.92(10) . . ?
O11 Mn1 O7 172.71(9) . 3_757 ?
O3 Mn2 O6 101.60(10) 4_565 2_646 ?
O3 Mn2 O7 104.25(9) 4_565 2_656 ?
O3 Mn2 O9 93.76(9) 4_565 . ?
O3 Mn2 O10 149.36(10) 4_565 . ?
O6 Mn2 O7 105.14(8) 2_646 2_656 ?
O6 Mn2 O9 98.04(10) 2_646 . ?
O6 Mn2 O10 94.61(11) 2_646 . ?
O7 Mn2 O9 146.82(9) 2_656 . ?
O7 Mn2 O10 96.21(9) 2_656 . ?
O10 Mn2 O9 58.03(9) . . ?
C1 O1 Mn1 121.36(18) . . ?
Mn1 O1W H1WA 109.4 . . ?
Mn1 O1W H1WB 109.4 . . ?
H1WA O1W H1WB 109.5 . . ?
C8 O3 Mn2 115.1(2) . 4_566 ?
C8 O4 Mn1 149.4(2) . 1_455 ?
C21 O5 Mn1 137.4(2) . 3_767 ?
C21 O6 Mn2 122.3(2) . 2_656 ?
Mn2 O7 Mn1 103.17(9) 2_646 3_757 ?
C22 O7 Mn1 133.42(18) . 3_757 ?
C22 O7 Mn2 102.04(18) . 2_646 ?
C23 O9 Mn2 90.63(19) . . ?
C23 O10 Mn2 92.19(19) . . ?
C24 O11 Mn1 148.1(3) . . ?
C24 N1 C25 121.1(3) . . ?
C24 N1 C26 120.7(4) . . ?
C25 N1 C26 117.9(4) . . ?
O1 C1 C2 117.6(3) . . ?
O2 C1 O1 124.8(3) . . ?
O2 C1 C2 117.6(3) . . ?
C3 C2 C1 120.5(3) . . ?
C7 C2 C1 119.8(3) . . ?
C7 C2 C3 119.6(3) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.8(3) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 C5 119.6(3) . . ?
C3 C4 C8 120.5(3) . . ?
C5 C4 C8 119.9(3) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 C4 121.7(3) . . ?
C6 C5 H5 119.2 . . ?
C5 C6 C7 117.4(3) . . ?
C5 C6 C9 122.6(3) . . ?
C7 C6 C9 120.1(3) . . ?
C2 C7 C6 121.8(3) . . ?
C2 C7 H7 119.1 . . ?
C6 C7 H7 119.1 . . ?
O3 C8 C4 118.0(3) . . ?
O4 C8 O3 124.4(3) . . ?
O4 C8 C4 117.6(3) . . ?
C10 C9 C6 121.1(3) . . ?
C10 C9 C14 116.7(3) . . ?
C14 C9 C6 122.2(3) . . ?
C9 C10 H10 118.6 . . ?
C11 C10 C9 122.8(3) . . ?
C11 C10 H10 118.6 . . ?
C10 C11 C15 117.4(3) . . ?
C12 C11 C10 119.0(3) . . ?
C12 C11 C15 123.6(3) . . ?
C11 C12 C13 118.6(3) . . ?
C11 C12 C23 123.3(3) . . ?
C13 C12 C23 118.1(3) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 C12 121.7(3) . . ?
C14 C13 H13 119.2 . . ?
C9 C14 H14 119.4 . . ?
C13 C14 C9 121.3(3) . . ?
C13 C14 H14 119.4 . . ?
C16 C15 C11 119.9(3) . . ?
C20 C15 C11 121.2(3) . . ?
C20 C15 C16 118.8(3) . . ?
C15 C16 H16 119.4 . . ?
C15 C16 C17 121.2(3) . . ?
C17 C16 H16 119.4 . . ?
C16 C17 C21 118.6(3) . . ?
C18 C17 C16 119.1(3) . . ?
C18 C17 C21 122.4(3) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 120.1(3) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 C20 120.0(3) . . ?
C18 C19 C22 120.5(3) . . ?
C20 C19 C22 119.5(3) . . ?
C15 C20 C19 120.7(3) . . ?
C15 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
O5 C21 O6 125.0(3) . . ?
O5 C21 C17 116.6(3) . . ?
O6 C21 C17 118.4(3) . . ?
O7 C22 C19 118.5(3) . . ?
O8 C22 O7 121.1(3) . . ?
O8 C22 C19 120.4(3) . . ?
O9 C23 C12 120.1(3) . . ?
O10 C23 O9 119.2(3) . . ?
O10 C23 C12 120.8(3) . . ?
O11 C24 N1 125.4(4) . . ?
O11 C24 H24 117.3 . . ?
N1 C24 H24 117.3 . . ?
N1 C25 H25A 109.5 . . ?
N1 C25 H25B 109.5 . . ?
N1 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N1 C26 H26A 109.5 . . ?
N1 C26 H26B 109.5 . . ?
N1 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
H2A N2 H2B 106.3 . . ?
C27 N2 H2A 106.0 . . ?
C27 N2 H2B 106.0 . . ?
C28 N2 H2A 106.0 . . ?
C28 N2 H2B 106.0 . . ?
C28 N2 C27 125.2(5) . . ?
N2 C27 H27A 109.5 . . ?
N2 C27 H27B 109.5 . . ?
N2 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
N2 C28 H28A 109.5 . . ?
N2 C28 H28B 109.5 . . ?
N2 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1W H1WA O2 0.96 2.02 2.728(3) 128.6 3_857
O1W H1WB O2 0.96 1.83 2.664(3) 142.9 .
C25 H25B O1 0.96 2.59 3.439(5) 147.9 .
N2 H2A O9 0.89 2.03 2.874(6) 156.8 1_455
N2 H2B O8 0.89 2.14 2.806(5) 131.2 .
C27 H27B O3 0.96 2.54 3.384(8) 147.2 4_465

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
Mn1 O1 C1 O2 33.6(4) . . . . ?
Mn1 O1 C1 C2 -145.4(2) . . . . ?
Mn1 O4 C8 O3 -39.5(6) 1_455 . . . ?
Mn1 O4 C8 C4 140.2(3) 1_455 . . . ?
Mn1 O5 C21 O6 30.8(5) 3_767 . . . ?
Mn1 O5 C21 C17 -150.0(2) 3_767 . . . ?
Mn1 O7 C22 O8 -120.6(3) 3_757 . . . ?
Mn1 O7 C22 C19 59.2(4) 3_757 . . . ?
Mn1 O11 C24 N1 65.1(7) . . . . ?
Mn2 O3 C8 O4 1.2(4) 4_566 . . . ?
Mn2 O3 C8 C4 -178.5(2) 4_566 . . . ?
Mn2 O6 C21 O5 13.5(4) 2_656 . . . ?
Mn2 O6 C21 C17 -165.6(2) 2_656 . . . ?
Mn2 O7 C22 O8 0.9(3) 2_646 . . . ?
Mn2 O7 C22 C19 -179.3(2) 2_646 . . . ?
Mn2 O9 C23 O10 -0.2(4) . . . . ?
Mn2 O9 C23 C12 -179.1(3) . . . . ?
Mn2 O10 C23 O9 0.3(4) . . . . ?
Mn2 O10 C23 C12 179.1(3) . . . . ?
O1 C1 C2 C3 -35.6(4) . . . . ?
O1 C1 C2 C7 146.2(3) . . . . ?
O2 C1 C2 C3 145.2(3) . . . . ?
O2 C1 C2 C7 -32.9(4) . . . . ?
C1 C2 C3 C4 -176.7(3) . . . . ?
C1 C2 C7 C6 -179.8(3) . . . . ?
C2 C3 C4 C5 -3.3(5) . . . . ?
C2 C3 C4 C8 174.5(3) . . . . ?
C3 C2 C7 C6 2.0(5) . . . . ?
C3 C4 C5 C6 1.8(5) . . . . ?
C3 C4 C8 O3 5.6(5) . . . . ?
C3 C4 C8 O4 -174.2(3) . . . . ?
C4 C5 C6 C7 1.6(5) . . . . ?
C4 C5 C6 C9 -179.9(3) . . . . ?
C5 C4 C8 O3 -176.6(3) . . . . ?
C5 C4 C8 O4 3.6(5) . . . . ?
C5 C6 C7 C2 -3.5(5) . . . . ?
C5 C6 C9 C10 -7.3(5) . . . . ?
C5 C6 C9 C14 173.8(3) . . . . ?
C6 C9 C10 C11 -179.5(3) . . . . ?
C6 C9 C14 C13 -179.8(3) . . . . ?
C7 C2 C3 C4 1.5(5) . . . . ?
C7 C6 C9 C10 171.2(3) . . . . ?
C7 C6 C9 C14 -7.7(5) . . . . ?
C8 C4 C5 C6 -176.1(3) . . . . ?
C9 C6 C7 C2 177.9(3) . . . . ?
C9 C10 C11 C12 -1.5(5) . . . . ?
C9 C10 C11 C15 178.5(3) . . . . ?
C10 C9 C14 C13 1.3(5) . . . . ?
C10 C11 C12 C13 2.7(5) . . . . ?
C10 C11 C12 C23 -174.9(3) . . . . ?
C10 C11 C15 C16 82.3(4) . . . . ?
C10 C11 C15 C20 -95.5(3) . . . . ?
C11 C12 C13 C14 -2.0(6) . . . . ?
C11 C12 C23 O9 -177.5(3) . . . . ?
C11 C12 C23 O10 3.7(5) . . . . ?
C11 C15 C16 C17 179.6(3) . . . . ?
C11 C15 C20 C19 179.1(3) . . . . ?
C12 C11 C15 C16 -97.7(4) . . . . ?
C12 C11 C15 C20 84.4(4) . . . . ?
C12 C13 C14 C9 0.0(6) . . . . ?
C13 C12 C23 O9 4.9(5) . . . . ?
C13 C12 C23 O10 -173.9(3) . . . . ?
C14 C9 C10 C11 -0.5(5) . . . . ?
C15 C11 C12 C13 -177.2(3) . . . . ?
C15 C11 C12 C23 5.2(5) . . . . ?
C15 C16 C17 C18 1.2(4) . . . . ?
C15 C16 C17 C21 -178.6(3) . . . . ?
C16 C15 C20 C19 1.2(4) . . . . ?
C16 C17 C18 C19 1.4(4) . . . . ?
C16 C17 C21 O5 -17.8(4) . . . . ?
C16 C17 C21 O6 161.4(3) . . . . ?
C17 C18 C19 C20 -2.8(4) . . . . ?
C17 C18 C19 C22 178.9(3) . . . . ?
C18 C17 C21 O5 162.4(3) . . . . ?
C18 C17 C21 O6 -18.4(4) . . . . ?
C18 C19 C20 C15 1.4(4) . . . . ?
C18 C19 C22 O7 -160.4(3) . . . . ?
C18 C19 C22 O8 19.4(4) . . . . ?
C20 C15 C16 C17 -2.5(4) . . . . ?
C20 C19 C22 O7 21.3(4) . . . . ?
C20 C19 C22 O8 -159.0(3) . . . . ?
C21 C17 C18 C19 -178.7(3) . . . . ?
C22 C19 C20 C15 179.8(3) . . . . ?
C23 C12 C13 C14 175.7(3) . . . . ?
C25 N1 C24 O11 1.7(6) . . . . ?
C26 N1 C24 O11 176.4(4) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
