# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017

####################################################################### 
# 
# 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. 
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data_spider-15058
_database_code_depnum_ccdc_archive 'CCDC 1529492'
_audit_update_record             
;
2017-03-18 deposited with the CCDC.
2017-06-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H36 Mn2 N4 O6, 2(N O3), 4(H2 O)'
_chemical_formula_sum            'C30 H44 Mn2 N6 O16'
_chemical_formula_weight         854.59

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 2/a'
_space_group_name_Hall           '-I 2ya'

_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+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   19.6402(13)
_cell_length_b                   8.4523(5)
_cell_length_c                   21.958(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.816(10)
_cell_angle_gamma                90
_cell_volume                     3637.0(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    13812
_cell_measurement_theta_min      3.2
_cell_measurement_theta_max      25.0

_exptl_crystal_description       Block
_exptl_crystal_colour            Red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.561
_exptl_crystal_F_000             1776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.775
_shelx_estimated_absorpt_T_min   0.860
_shelx_estimated_absorpt_T_max   0.926
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.794
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Tube'
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID imaging plate'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10
_diffrn_reflns_number            24035
_diffrn_reflns_av_unetI/netI     0.0718
_diffrn_reflns_av_R_equivalents  0.1417
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.177
_diffrn_reflns_theta_max         25.017
_diffrn_reflns_theta_full        25.017
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3198
_reflns_number_gt                2441
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
; 
Dolomanov, O.V.; Bourhis, L.J.; Gildea, R.J.; Howard, J.A.K.; Puschmann, H., 
OLEX2: A complete structure solution, refinement and analysis program
(2009). J. Appl. Cryst., 42, 339-341.
;
_computing_publication_material  'CIFTAB-2013/2 (Sheldrick, 2014)'
_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.

The hydrogen atoms were first found in the difference map, then generated
 geometrically and refined as riding atoms with C-H distances = 0.95- 0.99
 Å and Uiso(H) = 1.2 times Ueq(C) for CH and CH2 groups and Uiso(H)
 = 1.5 times Ueq(C) for CH3 groups.

 The protons on O3 were found in the difference map and refined as riding atoms.
 The protons on O4 were freely refined. The protons on O5 were geometrically
 placed and refined as a rigid group. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+16.4355P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     SHELXT
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3198
_refine_ls_number_parameters     264
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0890
_refine_ls_R_factor_gt           0.0625
_refine_ls_wR_factor_ref         0.0916
_refine_ls_wR_factor_gt          0.0844
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.2500 0.60649(10) 0.5000 0.0127(2) Uani 1 2 d S T P . .
Mn2 Mn 0.2500 0.98161(10) 0.5000 0.0146(2) Uani 1 2 d S T P . .
O1 O 0.18292(12) 0.4543(3) 0.49885(11) 0.0140(6) Uani 1 1 d . . . . .
O2 O 0.18459(12) 0.7721(3) 0.48818(11) 0.0145(6) Uani 1 1 d . . . . .
O3 O 0.30695(15) 1.1597(3) 0.54849(13) 0.0206(7) Uani 1 1 d . . . . .
H3A H 0.330(2) 1.154(5) 0.5803(19) 0.031 Uiso 1 1 d . U . . .
H3B H 0.313(2) 1.251(5) 0.5323(19) 0.031 Uiso 1 1 d . U . . .
N1 N 0.23834(15) 0.5923(4) 0.58879(14) 0.0149(7) Uani 1 1 d . . . . .
N2 N 0.18542(15) 0.9581(4) 0.58410(14) 0.0167(8) Uani 1 1 d . . . . .
C1 C 0.2841(2) 0.6364(5) 0.63423(17) 0.0196(9) Uani 1 1 d . . . . .
H1 H 0.3258 0.6840 0.6245 0.024 Uiso 1 1 calc R U . . .
C2 C 0.27128(19) 0.6133(5) 0.69460(17) 0.0214(9) Uani 1 1 d . . . . .
H2 H 0.3042 0.6420 0.7264 0.026 Uiso 1 1 calc R U . . .
C3 C 0.2095(2) 0.5474(5) 0.70787(18) 0.0238(10) Uani 1 1 d . . . . .
H3 H 0.1994 0.5326 0.7492 0.029 Uiso 1 1 calc R U . . .
C4 C 0.16225(19) 0.5027(5) 0.66135(17) 0.0192(9) Uani 1 1 d . . . . .
H4 H 0.1198 0.4573 0.6704 0.023 Uiso 1 1 calc R U . . .
C5 C 0.17803(18) 0.5256(4) 0.60189(17) 0.0143(9) Uani 1 1 d . . . . .
C6 C 0.09314(19) 0.3341(4) 0.55084(18) 0.0187(9) Uani 1 1 d . . . . .
H6A H 0.0693 0.3070 0.5116 0.028 Uiso 1 1 calc R U . . .
H6B H 0.0597 0.3520 0.5813 0.028 Uiso 1 1 calc R U . . .
H6C H 0.1235 0.2470 0.5642 0.028 Uiso 1 1 calc R U . . .
C7 C 0.13482(17) 0.4831(5) 0.54370(17) 0.0162(9) Uani 1 1 d . . . . .
C8 C 0.1933(2) 1.0445(5) 0.63563(17) 0.0199(9) Uani 1 1 d . . . . .
H8 H 0.2347 1.1013 0.6435 0.024 Uiso 1 1 calc R U . . .
C9 C 0.1444(2) 1.0547(5) 0.67748(18) 0.0202(10) Uani 1 1 d . . . . .
H9 H 0.1520 1.1167 0.7134 0.024 Uiso 1 1 calc R U . . .
C10 C 0.0837(2) 0.9725(5) 0.66626(18) 0.0220(9) Uani 1 1 d . . . . .
H10 H 0.0489 0.9778 0.6942 0.026 Uiso 1 1 calc R U . . .
C11 C 0.0749(2) 0.8833(5) 0.61401(18) 0.0218(9) Uani 1 1 d . . . . .
H11 H 0.0335 0.8270 0.6054 0.026 Uiso 1 1 calc R U . . .
C12 C 0.12673(19) 0.8752(5) 0.57358(17) 0.0166(9) Uani 1 1 d . . . . .
C13 C 0.07215(18) 0.8771(5) 0.46868(17) 0.0173(9) Uani 1 1 d . . . . .
H13A H 0.0904 0.9843 0.4646 0.026 Uiso 1 1 calc R U . . .
H13B H 0.0265 0.8829 0.4840 0.026 Uiso 1 1 calc R U . . .
H13C H 0.0695 0.8248 0.4288 0.026 Uiso 1 1 calc R U . . .
C14 C 0.11941(18) 0.7822(5) 0.51367(16) 0.0152(8) Uani 1 1 d . . . . .
C15 C 0.08730(18) 0.6177(4) 0.52109(17) 0.0159(9) Uani 1 1 d . . . . .
H15A H 0.0508 0.6279 0.5499 0.019 Uiso 1 1 calc R U . . .
H15B H 0.0652 0.5861 0.4811 0.019 Uiso 1 1 calc R U . . .
O4 O 0.36689(17) 1.1069(5) 0.65991(14) 0.0314(8) Uani 1 1 d . . . . .
H4A H 0.386(3) 1.032(7) 0.671(3) 0.07(2) Uiso 1 1 d . . . . .
H4B H 0.399(3) 1.181(8) 0.671(3) 0.09(2) Uiso 1 1 d . . . . .
O5 O 0.42300(15) 0.8302(4) 0.70848(15) 0.0370(8) Uani 1 1 d G . . . .
H5A H 0.4512 0.8574 0.7377 0.056 Uiso 1 1 d G U . . .
H5B H 0.4391 0.7526 0.6895 0.056 Uiso 1 1 d G U . . .
O6 O 0.49916(18) 0.5645(4) 0.68003(19) 0.0626(12) Uani 1 1 d . . . . .
O7 O 0.46588(18) 0.3291(4) 0.70010(15) 0.0504(10) Uani 1 1 d . . . . .
O8 O 0.43229(19) 0.4323(5) 0.61583(18) 0.0772(15) Uani 1 1 d . . . . .
N3 N 0.46544(19) 0.4440(5) 0.66450(19) 0.0335(10) Uani 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mn1 O1 1.840(2) 2_556 ?
Mn1 O1 1.840(2) . ?
Mn1 O2 1.906(3) 2_556 ?
Mn1 O2 1.906(2) . ?
Mn1 N1 1.982(3) . ?
Mn1 N1 1.982(3) 2_556 ?
Mn1 Mn2 3.1706(12) . ?
Mn2 O3 2.119(3) . ?
Mn2 O3 2.119(3) 2_556 ?
Mn2 O2 2.193(3) 2_556 ?
Mn2 O2 2.193(3) . ?
Mn2 N2 2.317(3) . ?
Mn2 N2 2.317(3) 2_556 ?
O1 C7 1.430(4) . ?
O2 C14 1.433(4) . ?
O3 H3A 0.81(4) . ?
O3 H3B 0.86(4) . ?
N1 C1 1.350(5) . ?
N1 C5 1.360(4) . ?
N2 C8 1.347(5) . ?
N2 C12 1.356(5) . ?
C1 C2 1.379(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.384(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.386(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.375(5) . ?
C4 H4 0.9500 . ?
C5 C7 1.529(5) . ?
C6 C7 1.515(5) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C15 1.533(5) . ?
C8 C9 1.375(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.387(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.374(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.396(5) . ?
C11 H11 0.9500 . ?
C12 C14 1.531(5) . ?
C13 C14 1.536(5) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.540(5) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
O4 H4A 0.76(6) . ?
O4 H4B 0.92(7) . ?
O5 H5A 0.8500 . ?
O5 H5B 0.8504 . ?
O6 N3 1.250(5) . ?
O7 N3 1.246(5) . ?
O8 N3 1.218(5) . ?

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 O1 91.29(15) 2_556 . ?
O1 Mn1 O2 92.07(10) 2_556 2_556 ?
O1 Mn1 O2 172.17(11) . 2_556 ?
O1 Mn1 O2 172.17(11) 2_556 . ?
O1 Mn1 O2 92.07(10) . . ?
O2 Mn1 O2 85.49(15) 2_556 . ?
O1 Mn1 N1 94.23(12) 2_556 . ?
O1 Mn1 N1 80.90(12) . . ?
O2 Mn1 N1 91.79(12) 2_556 . ?
O2 Mn1 N1 93.29(11) . . ?
O1 Mn1 N1 80.90(12) 2_556 2_556 ?
O1 Mn1 N1 94.23(12) . 2_556 ?
O2 Mn1 N1 93.29(11) 2_556 2_556 ?
O2 Mn1 N1 91.79(12) . 2_556 ?
N1 Mn1 N1 173.08(19) . 2_556 ?
O1 Mn1 Mn2 134.36(8) 2_556 . ?
O1 Mn1 Mn2 134.35(8) . . ?
O2 Mn1 Mn2 42.75(8) 2_556 . ?
O2 Mn1 Mn2 42.75(8) . . ?
N1 Mn1 Mn2 93.46(9) . . ?
N1 Mn1 Mn2 93.46(9) 2_556 . ?
O3 Mn2 O3 89.50(16) . 2_556 ?
O3 Mn2 O2 103.22(10) . 2_556 ?
O3 Mn2 O2 156.69(10) 2_556 2_556 ?
O3 Mn2 O2 156.69(10) . . ?
O3 Mn2 O2 103.22(10) 2_556 . ?
O2 Mn2 O2 72.29(13) 2_556 . ?
O3 Mn2 N2 87.65(11) . . ?
O3 Mn2 N2 99.36(11) 2_556 . ?
O2 Mn2 N2 100.60(10) 2_556 . ?
O2 Mn2 N2 71.20(10) . . ?
O3 Mn2 N2 99.36(11) . 2_556 ?
O3 Mn2 N2 87.66(11) 2_556 2_556 ?
O2 Mn2 N2 71.20(10) 2_556 2_556 ?
O2 Mn2 N2 100.60(10) . 2_556 ?
N2 Mn2 N2 170.17(16) . 2_556 ?
O3 Mn2 Mn1 135.25(8) . . ?
O3 Mn2 Mn1 135.25(8) 2_556 . ?
O2 Mn2 Mn1 36.14(6) 2_556 . ?
O2 Mn2 Mn1 36.14(6) . . ?
N2 Mn2 Mn1 85.09(8) . . ?
N2 Mn2 Mn1 85.09(8) 2_556 . ?
C7 O1 Mn1 112.1(2) . . ?
C14 O2 Mn1 127.0(2) . . ?
C14 O2 Mn2 115.9(2) . . ?
Mn1 O2 Mn2 101.11(10) . . ?
Mn2 O3 H3A 130(3) . . ?
Mn2 O3 H3B 121(3) . . ?
H3A O3 H3B 109(4) . . ?
C1 N1 C5 120.3(3) . . ?
C1 N1 Mn1 126.6(3) . . ?
C5 N1 Mn1 113.1(2) . . ?
C8 N2 C12 118.2(3) . . ?
C8 N2 Mn2 125.8(3) . . ?
C12 N2 Mn2 114.4(2) . . ?
N1 C1 C2 121.1(4) . . ?
N1 C1 H1 119.4 . . ?
C2 C1 H1 119.4 . . ?
C1 C2 C3 118.5(4) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C2 C3 C4 120.5(4) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 118.6(4) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
N1 C5 C4 120.9(3) . . ?
N1 C5 C7 111.3(3) . . ?
C4 C5 C7 127.8(3) . . ?
C7 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C7 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O1 C7 C6 108.4(3) . . ?
O1 C7 C5 105.1(3) . . ?
C6 C7 C5 112.5(3) . . ?
O1 C7 C15 108.6(3) . . ?
C6 C7 C15 109.2(3) . . ?
C5 C7 C15 112.8(3) . . ?
N2 C8 C9 123.3(4) . . ?
N2 C8 H8 118.3 . . ?
C9 C8 H8 118.3 . . ?
C8 C9 C10 118.7(4) . . ?
C8 C9 H9 120.7 . . ?
C10 C9 H9 120.7 . . ?
C11 C10 C9 118.8(4) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
C10 C11 C12 120.0(4) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
N2 C12 C11 120.9(4) . . ?
N2 C12 C14 116.2(3) . . ?
C11 C12 C14 122.7(3) . . ?
C14 C13 H13A 109.5 . . ?
C14 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C14 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O2 C14 C12 109.3(3) . . ?
O2 C14 C13 107.3(3) . . ?
C12 C14 C13 107.6(3) . . ?
O2 C14 C15 111.7(3) . . ?
C12 C14 C15 112.8(3) . . ?
C13 C14 C15 107.8(3) . . ?
C7 C15 C14 117.4(3) . . ?
C7 C15 H15A 108.0 . . ?
C14 C15 H15A 108.0 . . ?
C7 C15 H15B 108.0 . . ?
C14 C15 H15B 108.0 . . ?
H15A C15 H15B 107.2 . . ?
H4A O4 H4B 100(5) . . ?
H5A O5 H5B 109.5 . . ?
O8 N3 O7 117.9(4) . . ?
O8 N3 O6 123.2(5) . . ?
O7 N3 O6 118.8(4) . . ?

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
O1 Mn1 O1 C7 130.9(3) 2_556 . . . ?
O2 Mn1 O1 C7 -56.2(2) . . . . ?
N1 Mn1 O1 C7 36.8(2) . . . . ?
N1 Mn1 O1 C7 -148.2(2) 2_556 . . . ?
Mn2 Mn1 O1 C7 -49.1(3) . . . . ?
C5 N1 C1 C2 0.8(5) . . . . ?
Mn1 N1 C1 C2 -176.7(3) . . . . ?
N1 C1 C2 C3 -1.6(6) . . . . ?
C1 C2 C3 C4 1.3(6) . . . . ?
C2 C3 C4 C5 -0.1(6) . . . . ?
C1 N1 C5 C4 0.5(5) . . . . ?
Mn1 N1 C5 C4 178.3(3) . . . . ?
C1 N1 C5 C7 -179.2(3) . . . . ?
Mn1 N1 C5 C7 -1.3(4) . . . . ?
C3 C4 C5 N1 -0.8(6) . . . . ?
C3 C4 C5 C7 178.8(4) . . . . ?
Mn1 O1 C7 C6 -165.6(2) . . . . ?
Mn1 O1 C7 C5 -45.2(3) . . . . ?
Mn1 O1 C7 C15 75.8(3) . . . . ?
N1 C5 C7 O1 28.0(4) . . . . ?
C4 C5 C7 O1 -151.6(4) . . . . ?
N1 C5 C7 C6 145.8(3) . . . . ?
C4 C5 C7 C6 -33.9(5) . . . . ?
N1 C5 C7 C15 -90.2(4) . . . . ?
C4 C5 C7 C15 90.2(5) . . . . ?
C12 N2 C8 C9 -1.0(6) . . . . ?
Mn2 N2 C8 C9 163.4(3) . . . . ?
N2 C8 C9 C10 -0.2(6) . . . . ?
C8 C9 C10 C11 0.4(6) . . . . ?
C9 C10 C11 C12 0.6(6) . . . . ?
C8 N2 C12 C11 2.1(5) . . . . ?
Mn2 N2 C12 C11 -164.1(3) . . . . ?
C8 N2 C12 C14 178.5(3) . . . . ?
Mn2 N2 C12 C14 12.4(4) . . . . ?
C10 C11 C12 N2 -1.9(6) . . . . ?
C10 C11 C12 C14 -178.1(4) . . . . ?
Mn1 O2 C14 C12 92.8(3) . . . . ?
Mn2 O2 C14 C12 -36.6(3) . . . . ?
Mn1 O2 C14 C13 -150.8(2) . . . . ?
Mn2 O2 C14 C13 79.8(3) . . . . ?
Mn1 O2 C14 C15 -32.8(4) . . . . ?
Mn2 O2 C14 C15 -162.2(2) . . . . ?
N2 C12 C14 O2 14.3(4) . . . . ?
C11 C12 C14 O2 -169.3(3) . . . . ?
N2 C12 C14 C13 -101.9(4) . . . . ?
C11 C12 C14 C13 74.4(4) . . . . ?
N2 C12 C14 C15 139.3(3) . . . . ?
C11 C12 C14 C15 -44.4(5) . . . . ?
O1 C7 C15 C14 -64.7(4) . . . . ?
C6 C7 C15 C14 177.3(3) . . . . ?
C5 C7 C15 C14 51.4(4) . . . . ?
O2 C14 C15 C7 40.4(4) . . . . ?
C12 C14 C15 C7 -83.3(4) . . . . ?
C13 C14 C15 C7 158.0(3) . . . . ?

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
O3 H3A O4 0.81(4) 1.89(4) 2.681(4) 166(4) .
O3 H3B O1 0.86(4) 1.86(5) 2.711(4) 173(4) 2_566
O4 H4A O5 0.76(6) 2.01(6) 2.769(5) 171(6) .
O4 H4B O7 0.92(7) 1.89(7) 2.803(5) 175(6) 1_565
O4 H4B O8 0.92(7) 2.54(6) 3.212(6) 130(5) 1_565
O4 H4B N3 0.92(7) 2.58(7) 3.442(6) 157(5) 1_565
O5 H5A O6 0.85 2.65 3.428(5) 152.0 4_556
O5 H5A O7 0.85 2.07 2.865(4) 155.6 4_556
O5 H5B O6 0.85 2.00 2.792(5) 155.1 .

_refine_diff_density_max         0.334
_refine_diff_density_min         -0.400
_refine_diff_density_rms         0.080

####################################################################### 
# 
# 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_spider-15051
_database_code_depnum_ccdc_archive 'CCDC 1529493'
_audit_update_record             
;
2017-03-18 deposited with the CCDC.
2017-06-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C64 H70 Mn4 N8 O12, 2(F6 P), 2(C H2 Cl2)'
_chemical_formula_sum            'C66 H74 Cl4 F12 Mn4 N8 O12 P2'
_chemical_formula_weight         1822.83

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   20.2718(14)
_cell_length_b                   14.4091(10)
_cell_length_c                   24.8638(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     7262.7(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    4939
_cell_measurement_theta_min      1.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Plate
_exptl_crystal_colour            Orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.667
_exptl_crystal_F_000             3712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.968
_shelx_estimated_absorpt_T_min   0.830
_shelx_estimated_absorpt_T_max   0.953
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.668
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Tube'
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID imaging plate'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10
_diffrn_reflns_number            27738
_diffrn_reflns_av_unetI/netI     0.0758
_diffrn_reflns_av_R_equivalents  0.1153
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.009
_diffrn_reflns_theta_max         24.407
_diffrn_reflns_theta_full        24.407
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             5896
_reflns_number_gt                3777
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
; 
 'Rigaku R-AXIS RAPID, Rigaku R_AXIS RAPID imaging plate' 
;
_computing_publication_material  'CIFTAB-2013/2 (Sheldrick, 2014)'
_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 

The hydrogen atoms were first found in the difference map, then generated 
geometrically and refined as riding atoms with C-H distances = 0.95- 0.99 
angstroms and Uiso(H) = 1.2 times Ueq(C) for CH and CH2 groups and Uiso(H) 
= 1.5 times Ueq(C) for CH3 groups.

The PF6 group is disordered over two positions. The two groups were found in
the difference map and their site occupancies were freely refined to converged values of 
nearly equal values. The site occupancies were subsequently fixed at 0.50. The thermal parameters
of the fluorines were anticipated to be similar, and restrained to reflect this assertion. The
PF6 groups were expected to behave as rigid bodies and restrained with rigid bond restraints.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0587P)²+24.2386P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     SHELXT
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5896
_refine_ls_number_parameters     546
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1098
_refine_ls_R_factor_gt           0.0577
_refine_ls_wR_factor_ref         0.1513
_refine_ls_wR_factor_gt          0.1252
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.36953(4) 0.72245(6) 0.61857(3) 0.0174(2) Uani 1 1 d . . . . .
Mn2 Mn 0.45196(4) 0.87912(6) 0.55350(4) 0.0211(2) Uani 1 1 d . . . . .
O1 O 0.30334(16) 0.7255(3) 0.66882(15) 0.0202(8) Uani 1 1 d . . . . .
O2 O 0.37678(16) 0.8546(2) 0.61876(16) 0.0196(8) Uani 1 1 d . . . . .
O3 O 0.43239(15) 0.7257(2) 0.56066(15) 0.0190(8) Uani 1 1 d . . . . .
O4 O 0.37161(16) 0.5941(2) 0.62087(16) 0.0207(9) Uani 1 1 d . . . . .
O5 O 0.4991(2) 0.8873(3) 0.47832(18) 0.0370(11) Uani 1 1 d . . . . .
O6 O 0.51467(18) 0.9933(3) 0.41446(18) 0.0309(10) Uani 1 1 d . . . . .
N1 N 0.2923(2) 0.7229(3) 0.56828(19) 0.0194(10) Uani 1 1 d . . . . .
N2 N 0.3507(2) 0.9145(3) 0.5215(2) 0.0229(11) Uani 1 1 d . . . . .
N3 N 0.5412(2) 0.8097(3) 0.59124(19) 0.0221(11) Uani 1 1 d . . . . .
N4 N 0.44002(19) 0.7068(3) 0.67424(18) 0.0196(10) Uani 1 1 d . . . . .
C1 C 0.3370(3) 0.9239(4) 0.4688(3) 0.0272(14) Uani 1 1 d . . . . .
H1 H 0.3714 0.9128 0.4437 0.033 Uiso 1 1 calc R U . . .
C2 C 0.2759(3) 0.9489(4) 0.4492(3) 0.0298(14) Uani 1 1 d . . . . .
H2 H 0.2678 0.9526 0.4116 0.036 Uiso 1 1 calc R U . . .
C3 C 0.2266(3) 0.9685(4) 0.4864(3) 0.0318(15) Uani 1 1 d . . . . .
H3 H 0.1842 0.9883 0.4747 0.038 Uiso 1 1 calc R U . . .
C4 C 0.2398(3) 0.9589(4) 0.5406(3) 0.0259(14) Uani 1 1 d . . . . .
H4 H 0.2067 0.9724 0.5664 0.031 Uiso 1 1 calc R U . . .
C5 C 0.3014(2) 0.9294(4) 0.5571(2) 0.0201(12) Uani 1 1 d . . . . .
C6 C 0.3213(3) 0.9160(4) 0.6169(2) 0.0229(13) Uani 1 1 d . . . . .
C7 C 0.2645(3) 0.8810(4) 0.6531(2) 0.0231(13) Uani 1 1 d . . . . .
H7A H 0.2756 0.8969 0.6908 0.028 Uiso 1 1 calc R U . . .
H7B H 0.2243 0.9162 0.6436 0.028 Uiso 1 1 calc R U . . .
C8 C 0.2478(3) 0.7772(4) 0.6511(2) 0.0232(13) Uani 1 1 d . . . . .
C9 C 0.2354(2) 0.7457(4) 0.5942(2) 0.0192(12) Uani 1 1 d . . . . .
C10 C 0.1759(3) 0.7383(4) 0.5667(2) 0.0249(14) Uani 1 1 d . . . . .
H10 H 0.1356 0.7526 0.5844 0.030 Uiso 1 1 calc R U . . .
C11 C 0.1753(3) 0.7104(4) 0.5140(3) 0.0275(14) Uani 1 1 d . . . . .
H11 H 0.1347 0.7039 0.4954 0.033 Uiso 1 1 calc R U . . .
C12 C 0.2347(3) 0.6914(4) 0.4877(2) 0.0233(13) Uani 1 1 d . . . . .
H12 H 0.2353 0.6744 0.4507 0.028 Uiso 1 1 calc R U . . .
C13 C 0.2924(3) 0.6981(4) 0.5170(2) 0.0212(13) Uani 1 1 d . . . . .
H13 H 0.3332 0.6845 0.4999 0.025 Uiso 1 1 calc R U . . .
C14 C 0.3416(3) 1.0110(4) 0.6389(3) 0.0290(15) Uani 1 1 d . . . . .
H14A H 0.3596 1.0037 0.6752 0.044 Uiso 1 1 calc R U . . .
H14B H 0.3030 1.0518 0.6401 0.044 Uiso 1 1 calc R U . . .
H14C H 0.3752 1.0382 0.6153 0.044 Uiso 1 1 calc R U . . .
C15 C 0.1913(3) 0.7568(4) 0.6892(2) 0.0250(13) Uani 1 1 d . . . . .
H15A H 0.1827 0.6899 0.6897 0.038 Uiso 1 1 calc R U . . .
H15B H 0.1516 0.7896 0.6771 0.038 Uiso 1 1 calc R U . . .
H15C H 0.2030 0.7777 0.7255 0.038 Uiso 1 1 calc R U . . .
C16 C 0.5896(3) 0.8585(4) 0.6149(2) 0.0271(14) Uani 1 1 d . . . . .
H16 H 0.5852 0.9239 0.6177 0.032 Uiso 1 1 calc R U . . .
C17 C 0.6459(3) 0.8167(5) 0.6353(3) 0.0317(15) Uani 1 1 d . . . . .
H17 H 0.6788 0.8525 0.6530 0.038 Uiso 1 1 calc R U . . .
C18 C 0.6530(3) 0.7229(5) 0.6296(3) 0.0335(16) Uani 1 1 d . . . . .
H18 H 0.6917 0.6930 0.6425 0.040 Uiso 1 1 calc R U . . .
C19 C 0.6039(3) 0.6716(4) 0.6050(2) 0.0262(14) Uani 1 1 d . . . . .
H19 H 0.6087 0.6065 0.6004 0.031 Uiso 1 1 calc R U . . .
C20 C 0.5467(2) 0.7176(4) 0.5870(2) 0.0235(13) Uani 1 1 d . . . . .
C21 C 0.4897(2) 0.6685(4) 0.5571(2) 0.0198(12) Uani 1 1 d . . . . .
C22 C 0.4762(3) 0.5699(4) 0.5775(3) 0.0249(14) Uani 1 1 d . . . . .
H22A H 0.4526 0.5357 0.5488 0.030 Uiso 1 1 calc R U . . .
H22B H 0.5192 0.5386 0.5829 0.030 Uiso 1 1 calc R U . . .
C23 C 0.4365(2) 0.5603(4) 0.6293(2) 0.0233(13) Uani 1 1 d . . . . .
C24 C 0.4668(2) 0.6202(4) 0.6733(2) 0.0219(13) Uani 1 1 d . . . . .
C25 C 0.5172(3) 0.5975(4) 0.7081(3) 0.0301(15) Uani 1 1 d . . . . .
H25 H 0.5351 0.5366 0.7082 0.036 Uiso 1 1 calc R U . . .
C26 C 0.5412(3) 0.6637(5) 0.7425(3) 0.0369(16) Uani 1 1 d . . . . .
H26 H 0.5769 0.6494 0.7658 0.044 Uiso 1 1 calc R U . . .
C27 C 0.5133(3) 0.7511(5) 0.7432(3) 0.0348(16) Uani 1 1 d . . . . .
H27 H 0.5293 0.7972 0.7672 0.042 Uiso 1 1 calc R U . . .
C28 C 0.4622(3) 0.7709(4) 0.7089(2) 0.0266(14) Uani 1 1 d . . . . .
H28 H 0.4423 0.8305 0.7097 0.032 Uiso 1 1 calc R U . . .
C29 C 0.5101(3) 0.6624(4) 0.4979(3) 0.0283(14) Uani 1 1 d . . . . .
H29A H 0.4746 0.6334 0.4772 0.042 Uiso 1 1 calc R U . . .
H29B H 0.5503 0.6250 0.4948 0.042 Uiso 1 1 calc R U . . .
H29C H 0.5185 0.7249 0.4840 0.042 Uiso 1 1 calc R U . . .
C30 C 0.4316(3) 0.4585(4) 0.6461(3) 0.0299(15) Uani 1 1 d . . . . .
H30A H 0.4047 0.4534 0.6787 0.045 Uiso 1 1 calc R U . . .
H30B H 0.4759 0.4342 0.6532 0.045 Uiso 1 1 calc R U . . .
H30C H 0.4112 0.4225 0.6171 0.045 Uiso 1 1 calc R U . . .
C31 C 0.5030(3) 0.9129(5) 0.4304(3) 0.0309(15) Uani 1 1 d . . . . .
C32 C 0.4961(3) 0.8400(5) 0.3864(3) 0.0422(17) Uani 1 1 d . . . . .
H32A H 0.4613 0.8589 0.3613 0.063 Uiso 1 1 calc R U . . .
H32B H 0.4845 0.7802 0.4026 0.063 Uiso 1 1 calc R U . . .
H32C H 0.5380 0.8342 0.3670 0.063 Uiso 1 1 calc R U . . .
Cl1 Cl 0.24613(9) 0.55796(14) 0.77860(8) 0.0555(5) Uani 1 1 d . . . . .
Cl2 Cl 0.38601(10) 0.52967(18) 0.79096(10) 0.0744(7) Uani 1 1 d . . . . .
P1 P 0.14453(8) 0.36322(13) 0.85056(7) 0.0349(4) Uani 1 1 d . . . . .
C33 C 0.3238(3) 0.5973(5) 0.7628(4) 0.057(2) Uani 1 1 d . . . . .
H33A H 0.3286 0.6620 0.7757 0.069 Uiso 1 1 calc R U . . .
H33B H 0.3290 0.5978 0.7233 0.069 Uiso 1 1 calc R U . . .
F1A F 0.1582(12) 0.267(2) 0.8804(14) 0.058(8) Uani 0.5 1 d . . P A 1
F2A F 0.2102(11) 0.4056(19) 0.8732(13) 0.059(8) Uani 0.5 1 d . . P A 1
F3A F 0.1064(9) 0.3946(17) 0.9070(9) 0.081(6) Uani 0.5 1 d . . P A 1
F4A F 0.0738(6) 0.3354(9) 0.8322(7) 0.067(4) Uani 0.5 1 d . . P A 1
F5A F 0.1766(8) 0.331(2) 0.7998(11) 0.078(6) Uani 0.5 1 d . . P A 1
F6A F 0.1282(9) 0.4658(10) 0.8256(7) 0.060(5) Uani 0.5 1 d . . P A 1
F1B F 0.1591(16) 0.286(2) 0.8908(13) 0.072(10) Uani 0.5 1 d . . P A 2
F2B F 0.2030(12) 0.4167(17) 0.8779(13) 0.058(7) Uani 0.5 1 d . . P A 2
F3B F 0.0954(12) 0.409(2) 0.8879(9) 0.115(10) Uani 0.5 1 d . . P A 2
F4B F 0.0934(7) 0.2929(9) 0.8205(5) 0.068(4) Uani 0.5 1 d . . P A 2
F5B F 0.2015(8) 0.3252(19) 0.8082(11) 0.058(4) Uani 0.5 1 d . . P A 2
F6B F 0.1309(9) 0.4330(11) 0.8053(8) 0.075(6) Uani 0.5 1 d . . 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
Mn1 O1 1.834(4) . ?
Mn1 O4 1.851(4) . ?
Mn1 O2 1.909(4) . ?
Mn1 O3 1.923(4) . ?
Mn1 N4 2.002(4) . ?
Mn1 N1 2.003(4) . ?
Mn2 O5 2.103(4) . ?
Mn2 O6 2.115(4) 5_676 ?
Mn2 O3 2.253(4) . ?
Mn2 O2 2.254(4) . ?
Mn2 N2 2.260(4) . ?
Mn2 N3 2.269(5) . ?
O1 C8 1.421(6) . ?
O2 C6 1.431(6) . ?
O3 C21 1.427(6) . ?
O4 C23 1.418(6) . ?
O5 C31 1.249(8) . ?
O6 C31 1.247(7) . ?
O6 Mn2 2.115(4) 5_676 ?
N1 C13 1.324(7) . ?
N1 C9 1.362(7) . ?
N2 C1 1.346(8) . ?
N2 C5 1.352(7) . ?
N3 C20 1.336(7) . ?
N3 C16 1.343(7) . ?
N4 C28 1.340(7) . ?
N4 C24 1.361(7) . ?
C1 C2 1.380(8) . ?
C1 H1 0.9500 . ?
C2 C3 1.392(9) . ?
C2 H2 0.9500 . ?
C3 C4 1.380(9) . ?
C3 H3 0.9500 . ?
C4 C5 1.382(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.552(8) . ?
C6 C14 1.530(8) . ?
C6 C7 1.546(8) . ?
C7 C8 1.536(8) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.506(8) . ?
C8 C15 1.516(7) . ?
C9 C10 1.391(7) . ?
C10 C11 1.370(8) . ?
C10 H10 0.9500 . ?
C11 C12 1.396(8) . ?
C11 H11 0.9500 . ?
C12 C13 1.383(8) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.386(8) . ?
C16 H16 0.9500 . ?
C17 C18 1.367(9) . ?
C17 H17 0.9500 . ?
C18 C19 1.382(9) . ?
C18 H18 0.9500 . ?
C19 C20 1.410(8) . ?
C19 H19 0.9500 . ?
C20 C21 1.545(8) . ?
C21 C29 1.532(8) . ?
C21 C22 1.533(8) . ?
C22 C23 1.525(8) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.523(8) . ?
C23 C30 1.529(8) . ?
C24 C25 1.378(8) . ?
C25 C26 1.372(9) . ?
C25 H25 0.9500 . ?
C26 C27 1.382(9) . ?
C26 H26 0.9500 . ?
C27 C28 1.371(8) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 C32 1.523(9) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
Cl1 C33 1.719(7) . ?
Cl2 C33 1.740(7) . ?
P1 F5A 1.49(3) . ?
P1 F3B 1.51(2) . ?
P1 F1B 1.52(3) . ?
P1 F6B 1.53(2) . ?
P1 F4A 1.558(13) . ?
P1 F2B 1.57(2) . ?
P1 F2A 1.57(2) . ?
P1 F1A 1.60(3) . ?
P1 F4B 1.630(13) . ?
P1 F6A 1.637(15) . ?
P1 F5B 1.66(2) . ?
P1 F3A 1.66(2) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?

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 O4 91.11(16) . . ?
O1 Mn1 O2 91.78(16) . . ?
O4 Mn1 O2 173.96(15) . . ?
O1 Mn1 O3 173.83(16) . . ?
O4 Mn1 O3 91.85(16) . . ?
O2 Mn1 O3 85.79(16) . . ?
O1 Mn1 N4 93.08(17) . . ?
O4 Mn1 N4 81.36(17) . . ?
O2 Mn1 N4 93.18(17) . . ?
O3 Mn1 N4 92.72(16) . . ?
O1 Mn1 N1 81.58(17) . . ?
O4 Mn1 N1 92.31(17) . . ?
O2 Mn1 N1 93.36(17) . . ?
O3 Mn1 N1 92.89(17) . . ?
N4 Mn1 N1 171.67(19) . . ?
O5 Mn2 O6 98.10(18) . 5_676 ?
O5 Mn2 O3 101.83(16) . . ?
O6 Mn2 O3 151.60(16) 5_676 . ?
O5 Mn2 O2 162.96(16) . . ?
O6 Mn2 O2 94.68(15) 5_676 . ?
O3 Mn2 O2 70.74(13) . . ?
O5 Mn2 N2 95.03(17) . . ?
O6 Mn2 N2 103.13(16) 5_676 . ?
O3 Mn2 N2 95.11(14) . . ?
O2 Mn2 N2 71.00(15) . . ?
O5 Mn2 N3 91.71(17) . . ?
O6 Mn2 N3 88.42(16) 5_676 . ?
O3 Mn2 N3 71.06(14) . . ?
O2 Mn2 N3 99.91(15) . . ?
N2 Mn2 N3 165.63(17) . . ?
C8 O1 Mn1 112.4(3) . . ?
C6 O2 Mn1 123.8(3) . . ?
C6 O2 Mn2 114.3(3) . . ?
Mn1 O2 Mn2 101.93(16) . . ?
C21 O3 Mn1 124.8(3) . . ?
C21 O3 Mn2 114.7(3) . . ?
Mn1 O3 Mn2 101.51(15) . . ?
C23 O4 Mn1 111.6(3) . . ?
C31 O5 Mn2 153.2(4) . . ?
C31 O6 Mn2 138.4(4) . 5_676 ?
C13 N1 C9 121.5(5) . . ?
C13 N1 Mn1 126.8(4) . . ?
C9 N1 Mn1 111.6(4) . . ?
C1 N2 C5 118.0(5) . . ?
C1 N2 Mn2 123.5(4) . . ?
C5 N2 Mn2 118.4(4) . . ?
C20 N3 C16 119.5(5) . . ?
C20 N3 Mn2 118.2(4) . . ?
C16 N3 Mn2 122.2(4) . . ?
C28 N4 C24 120.6(5) . . ?
C28 N4 Mn1 127.3(4) . . ?
C24 N4 Mn1 112.1(4) . . ?
N2 C1 C2 123.8(6) . . ?
N2 C1 H1 118.1 . . ?
C2 C1 H1 118.1 . . ?
C1 C2 C3 117.5(6) . . ?
C1 C2 H2 121.2 . . ?
C3 C2 H2 121.2 . . ?
C4 C3 C2 119.3(5) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 119.8(6) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
N2 C5 C4 121.4(5) . . ?
N2 C5 C6 114.6(4) . . ?
C4 C5 C6 123.9(5) . . ?
O2 C6 C14 109.3(4) . . ?
O2 C6 C7 111.4(5) . . ?
C14 C6 C7 106.5(5) . . ?
O2 C6 C5 108.2(4) . . ?
C14 C6 C5 107.4(5) . . ?
C7 C6 C5 113.9(4) . . ?
C8 C7 C6 117.5(4) . . ?
C8 C7 H7A 107.9 . . ?
C6 C7 H7A 107.9 . . ?
C8 C7 H7B 107.9 . . ?
C6 C7 H7B 107.9 . . ?
H7A C7 H7B 107.2 . . ?
O1 C8 C9 105.5(4) . . ?
O1 C8 C15 107.6(5) . . ?
C9 C8 C15 113.8(5) . . ?
O1 C8 C7 108.9(4) . . ?
C9 C8 C7 111.2(5) . . ?
C15 C8 C7 109.6(4) . . ?
N1 C9 C10 118.9(5) . . ?
N1 C9 C8 112.0(4) . . ?
C10 C9 C8 129.1(5) . . ?
C11 C10 C9 120.0(5) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 120.0(5) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C13 C12 C11 117.9(6) . . ?
C13 C12 H12 121.1 . . ?
C11 C12 H12 121.1 . . ?
N1 C13 C12 121.7(5) . . ?
N1 C13 H13 119.1 . . ?
C12 C13 H13 119.1 . . ?
C6 C14 H14A 109.5 . . ?
C6 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C6 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C8 C15 H15A 109.5 . . ?
C8 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C8 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N3 C16 C17 122.4(6) . . ?
N3 C16 H16 118.8 . . ?
C17 C16 H16 118.8 . . ?
C18 C17 C16 118.5(6) . . ?
C18 C17 H17 120.7 . . ?
C16 C17 H17 120.7 . . ?
C17 C18 C19 120.0(6) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C18 C19 C20 118.8(6) . . ?
C18 C19 H19 120.6 . . ?
C20 C19 H19 120.6 . . ?
N3 C20 C19 120.8(5) . . ?
N3 C20 C21 115.5(5) . . ?
C19 C20 C21 123.5(5) . . ?
O3 C21 C29 108.2(4) . . ?
O3 C21 C22 111.7(4) . . ?
C29 C21 C22 108.2(5) . . ?
O3 C21 C20 108.4(4) . . ?
C29 C21 C20 106.7(4) . . ?
C22 C21 C20 113.6(5) . . ?
C23 C22 C21 117.2(5) . . ?
C23 C22 H22A 108.0 . . ?
C21 C22 H22A 108.0 . . ?
C23 C22 H22B 108.0 . . ?
C21 C22 H22B 108.0 . . ?
H22A C22 H22B 107.2 . . ?
O4 C23 C24 106.6(4) . . ?
O4 C23 C22 109.5(5) . . ?
C24 C23 C22 110.0(4) . . ?
O4 C23 C30 108.1(4) . . ?
C24 C23 C30 111.9(5) . . ?
C22 C23 C30 110.6(5) . . ?
N4 C24 C25 120.2(5) . . ?
N4 C24 C23 111.8(4) . . ?
C25 C24 C23 128.0(5) . . ?
C26 C25 C24 119.4(6) . . ?
C26 C25 H25 120.3 . . ?
C24 C25 H25 120.3 . . ?
C25 C26 C27 119.7(6) . . ?
C25 C26 H26 120.1 . . ?
C27 C26 H26 120.1 . . ?
C28 C27 C26 119.4(6) . . ?
C28 C27 H27 120.3 . . ?
C26 C27 H27 120.3 . . ?
N4 C28 C27 120.7(6) . . ?
N4 C28 H28 119.6 . . ?
C27 C28 H28 119.6 . . ?
C21 C29 H29A 109.5 . . ?
C21 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C21 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C23 C30 H30A 109.5 . . ?
C23 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C23 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
O6 C31 O5 126.2(6) . . ?
O6 C31 C32 115.4(6) . . ?
O5 C31 C32 118.4(6) . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
F3B P1 F1B 92.5(16) . . ?
F3B P1 F6B 92.5(10) . . ?
F1B P1 F6B 173.8(14) . . ?
F5A P1 F4A 94.2(9) . . ?
F3B P1 F2B 90.9(17) . . ?
F1B P1 F2B 85.9(15) . . ?
F6B P1 F2B 97.6(12) . . ?
F5A P1 F2A 93.1(15) . . ?
F4A P1 F2A 170.6(12) . . ?
F5A P1 F1A 92.9(17) . . ?
F4A P1 F1A 94.2(11) . . ?
F2A P1 F1A 91.4(13) . . ?
F3B P1 F4B 97.8(13) . . ?
F1B P1 F4B 88.3(13) . . ?
F6B P1 F4B 87.5(8) . . ?
F2B P1 F4B 169.7(12) . . ?
F5A P1 F6A 92.6(14) . . ?
F4A P1 F6A 86.2(8) . . ?
F2A P1 F6A 87.5(11) . . ?
F1A P1 F6A 174.5(14) . . ?
F3B P1 F5B 173.3(15) . . ?
F1B P1 F5B 92.4(16) . . ?
F6B P1 F5B 82.9(11) . . ?
F2B P1 F5B 84.9(14) . . ?
F4B P1 F5B 86.9(9) . . ?
F5A P1 F3A 177.4(13) . . ?
F4A P1 F3A 83.7(9) . . ?
F2A P1 F3A 89.2(15) . . ?
F1A P1 F3A 85.7(14) . . ?
F6A P1 F3A 88.9(10) . . ?
Cl1 C33 Cl2 112.8(4) . . ?
Cl1 C33 H33A 109.0 . . ?
Cl2 C33 H33A 109.0 . . ?
Cl1 C33 H33B 109.0 . . ?
Cl2 C33 H33B 109.0 . . ?
H33A C33 H33B 107.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O4 Mn1 O1 C8 -126.1(3) . . . . ?
O2 Mn1 O1 C8 59.3(4) . . . . ?
N4 Mn1 O1 C8 152.5(4) . . . . ?
N1 Mn1 O1 C8 -33.9(3) . . . . ?
O1 Mn1 O4 C23 -128.5(4) . . . . ?
O3 Mn1 O4 C23 56.9(4) . . . . ?
N4 Mn1 O4 C23 -35.6(4) . . . . ?
N1 Mn1 O4 C23 149.8(4) . . . . ?
C5 N2 C1 C2 0.7(8) . . . . ?
Mn2 N2 C1 C2 -177.5(4) . . . . ?
N2 C1 C2 C3 2.4(9) . . . . ?
C1 C2 C3 C4 -2.4(9) . . . . ?
C2 C3 C4 C5 -0.4(9) . . . . ?
C1 N2 C5 C4 -3.7(8) . . . . ?
Mn2 N2 C5 C4 174.5(4) . . . . ?
C1 N2 C5 C6 179.3(5) . . . . ?
Mn2 N2 C5 C6 -2.4(6) . . . . ?
C3 C4 C5 N2 3.6(8) . . . . ?
C3 C4 C5 C6 -179.7(5) . . . . ?
Mn1 O2 C6 C14 158.5(4) . . . . ?
Mn2 O2 C6 C14 -76.4(5) . . . . ?
Mn1 O2 C6 C7 41.1(6) . . . . ?
Mn2 O2 C6 C7 166.1(3) . . . . ?
Mn1 O2 C6 C5 -84.9(5) . . . . ?
Mn2 O2 C6 C5 40.2(5) . . . . ?
N2 C5 C6 O2 -24.3(6) . . . . ?
C4 C5 C6 O2 158.8(5) . . . . ?
N2 C5 C6 C14 93.5(5) . . . . ?
C4 C5 C6 C14 -83.3(6) . . . . ?
N2 C5 C6 C7 -148.8(5) . . . . ?
C4 C5 C6 C7 34.3(7) . . . . ?
O2 C6 C7 C8 -43.8(7) . . . . ?
C14 C6 C7 C8 -162.9(5) . . . . ?
C5 C6 C7 C8 79.0(6) . . . . ?
Mn1 O1 C8 C9 45.4(5) . . . . ?
Mn1 O1 C8 C15 167.2(4) . . . . ?
Mn1 O1 C8 C7 -74.1(5) . . . . ?
C6 C7 C8 O1 62.4(6) . . . . ?
C6 C7 C8 C9 -53.5(6) . . . . ?
C6 C7 C8 C15 179.9(5) . . . . ?
C13 N1 C9 C10 3.2(8) . . . . ?
Mn1 N1 C9 C10 -172.3(4) . . . . ?
C13 N1 C9 C8 -176.5(5) . . . . ?
Mn1 N1 C9 C8 8.1(5) . . . . ?
O1 C8 C9 N1 -32.7(6) . . . . ?
C15 C8 C9 N1 -150.5(5) . . . . ?
C7 C8 C9 N1 85.2(5) . . . . ?
O1 C8 C9 C10 147.6(5) . . . . ?
C15 C8 C9 C10 29.9(8) . . . . ?
C7 C8 C9 C10 -94.4(7) . . . . ?
N1 C9 C10 C11 -1.4(8) . . . . ?
C8 C9 C10 C11 178.2(6) . . . . ?
C9 C10 C11 C12 -1.4(9) . . . . ?
C10 C11 C12 C13 2.6(8) . . . . ?
C9 N1 C13 C12 -2.0(8) . . . . ?
Mn1 N1 C13 C12 172.7(4) . . . . ?
C11 C12 C13 N1 -0.9(8) . . . . ?
C20 N3 C16 C17 0.0(9) . . . . ?
Mn2 N3 C16 C17 -176.3(4) . . . . ?
N3 C16 C17 C18 2.1(9) . . . . ?
C16 C17 C18 C19 -1.6(9) . . . . ?
C17 C18 C19 C20 -0.9(9) . . . . ?
C16 N3 C20 C19 -2.6(8) . . . . ?
Mn2 N3 C20 C19 173.9(4) . . . . ?
C16 N3 C20 C21 -177.6(5) . . . . ?
Mn2 N3 C20 C21 -1.1(6) . . . . ?
C18 C19 C20 N3 3.0(9) . . . . ?
C18 C19 C20 C21 177.6(5) . . . . ?
Mn1 O3 C21 C29 157.2(3) . . . . ?
Mn2 O3 C21 C29 -76.8(4) . . . . ?
Mn1 O3 C21 C22 38.3(6) . . . . ?
Mn2 O3 C21 C22 164.3(4) . . . . ?
Mn1 O3 C21 C20 -87.6(5) . . . . ?
Mn2 O3 C21 C20 38.5(5) . . . . ?
N3 C20 C21 O3 -24.1(7) . . . . ?
C19 C20 C21 O3 161.1(5) . . . . ?
N3 C20 C21 C29 92.2(6) . . . . ?
C19 C20 C21 C29 -82.7(7) . . . . ?
N3 C20 C21 C22 -148.8(5) . . . . ?
C19 C20 C21 C22 36.4(8) . . . . ?
O3 C21 C22 C23 -43.7(7) . . . . ?
C29 C21 C22 C23 -162.6(5) . . . . ?
C20 C21 C22 C23 79.2(6) . . . . ?
Mn1 O4 C23 C24 44.1(5) . . . . ?
Mn1 O4 C23 C22 -74.9(5) . . . . ?
Mn1 O4 C23 C30 164.6(4) . . . . ?
C21 C22 C23 O4 65.1(6) . . . . ?
C21 C22 C23 C24 -51.8(6) . . . . ?
C21 C22 C23 C30 -176.0(5) . . . . ?
C28 N4 C24 C25 -0.1(8) . . . . ?
Mn1 N4 C24 C25 178.5(4) . . . . ?
C28 N4 C24 C23 -177.4(5) . . . . ?
Mn1 N4 C24 C23 1.2(5) . . . . ?
O4 C23 C24 N4 -27.7(6) . . . . ?
C22 C23 C24 N4 91.0(5) . . . . ?
C30 C23 C24 N4 -145.7(5) . . . . ?
O4 C23 C24 C25 155.3(6) . . . . ?
C22 C23 C24 C25 -86.0(7) . . . . ?
C30 C23 C24 C25 37.3(8) . . . . ?
N4 C24 C25 C26 -1.7(9) . . . . ?
C23 C24 C25 C26 175.0(6) . . . . ?
C24 C25 C26 C27 2.1(9) . . . . ?
C25 C26 C27 C28 -0.7(10) . . . . ?
C24 N4 C28 C27 1.5(8) . . . . ?
Mn1 N4 C28 C27 -176.8(4) . . . . ?
C26 C27 C28 N4 -1.1(9) . . . . ?
Mn2 O6 C31 O5 12.2(9) 5_676 . . . ?
Mn2 O6 C31 C32 -164.8(4) 5_676 . . . ?
Mn2 O5 C31 O6 73.2(11) . . . . ?
Mn2 O5 C31 C32 -109.8(10) . . . . ?

_refine_diff_density_max         0.790
_refine_diff_density_min         -0.799
_refine_diff_density_rms         0.099

####################################################################### 
# 
# 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_007-16022-mDL-final
_database_code_depnum_ccdc_archive 'CCDC 1529458'
_audit_update_record             
;
2017-03-18 deposited with the CCDC.
2017-06-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H18 N2 O2, H2 O'
_chemical_formula_sum            'C15 H20 N2 O3'
_chemical_formula_weight         276.33

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'
N N 0.0311 0.0180 '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'

_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                   8.32500(10)
_cell_length_b                   10.87670(10)
_cell_length_c                   8.5879(6)
_cell_angle_alpha                90
_cell_angle_beta                 110.364(8)
_cell_angle_gamma                90
_cell_volume                     729.02(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    23317
_cell_measurement_theta_min      5.5
_cell_measurement_theta_max      66.6

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_F_000             296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.719
_shelx_estimated_absorpt_T_min   0.870
_shelx_estimated_absorpt_T_max   0.932
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.853
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   'microfocus rotating anode'
_diffrn_measurement_device_type  'Rigaku Saturn 944+ CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 22.2
_diffrn_reflns_number            24343
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         5.495
_diffrn_reflns_theta_max         66.582
_diffrn_reflns_theta_full        66.582
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2573
_reflns_number_gt                2485
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.888
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    0.997

_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       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
; 
Dolomanov, O.V.; Bourhis, L.J.; Gildea, R.J.; Howard, J.A.K.; Puschmann, H., 
OLEX2: A complete structure solution, refinement and analysis program 
(2009). J. Appl. Cryst., 42, 339-341. 
;
_computing_publication_material  'CIFTAB-2014/2 (Sheldrick, 2014)'
_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 

 The hydrogen atoms were first found in the difference map, then generated 
 geometrically and refined as riding atoms with C-H distances = 0.95- 0.99 
 Å and Uiso(H) = 1.2 times Ueq(C) for CH and CH2 groups and Uiso(H) 
 = 1.5 times Ueq(C) for CH3 groups. The only exceptions are H1, H2, H3a and H3b
 which were found in the difference map and semi-freely refined with a distance 
 restraint of 0.85(2) Å.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0260P)²+0.1500P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     SHELXT
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1119 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.02(8)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2573
_refine_ls_number_parameters     199
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0276
_refine_ls_R_factor_gt           0.0263
_refine_ls_wR_factor_ref         0.0623
_refine_ls_wR_factor_gt          0.0616
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.41366(19) 0.37871(13) 0.22744(18) 0.0254(3) Uani 1 1 d D . . . .
H1 H 0.454(4) 0.412(3) 0.324(3) 0.069(11) Uiso 1 1 d D . . . .
O2 O 0.55765(18) 0.53581(13) 0.46706(17) 0.0231(3) Uani 1 1 d D . . . .
H2 H 0.594(4) 0.562(3) 0.572(3) 0.067(10) Uiso 1 1 d D . . . .
N1 N 0.7190(2) 0.45757(16) 0.0237(2) 0.0254(4) Uani 1 1 d . . . . .
N2 N 0.8648(2) 0.68434(17) 0.3125(2) 0.0271(4) Uani 1 1 d . . . . .
C1 C 0.8663(3) 0.4138(2) 0.0157(3) 0.0316(5) Uani 1 1 d . . . . .
H1A H 0.9174 0.4561 -0.0520 0.038 Uiso 1 1 calc R U . . .
C2 C 0.9482(3) 0.3103(2) 0.1005(3) 0.0319(5) Uani 1 1 d . . . . .
H2A H 1.0534 0.2827 0.0927 0.038 Uiso 1 1 calc R U . . .
C3 C 0.8721(3) 0.2489(2) 0.1963(3) 0.0290(5) Uani 1 1 d . . . . .
H3 H 0.9240 0.1771 0.2556 0.035 Uiso 1 1 calc R U . . .
C4 C 0.7194(3) 0.29208(19) 0.2060(3) 0.0250(4) Uani 1 1 d . . . . .
H4 H 0.6653 0.2500 0.2712 0.030 Uiso 1 1 calc R U . . .
C5 C 0.6463(2) 0.39755(18) 0.1194(2) 0.0202(4) Uani 1 1 d . . . . .
C6 C 0.3424(3) 0.4445(2) -0.0509(2) 0.0257(4) Uani 1 1 d . . . . .
H6A H 0.3228 0.3582 -0.0848 0.039 Uiso 1 1 calc R U . . .
H6B H 0.3823 0.4893 -0.1296 0.039 Uiso 1 1 calc R U . . .
H6C H 0.2352 0.4810 -0.0497 0.039 Uiso 1 1 calc R U . . .
C7 C 0.4779(2) 0.45227(18) 0.1227(2) 0.0204(4) Uani 1 1 d . . . . .
C8 C 0.4954(2) 0.58744(17) 0.1808(2) 0.0194(4) Uani 1 1 d . . . . .
H8A H 0.5408 0.6348 0.1067 0.023 Uiso 1 1 calc R U . . .
H8B H 0.3787 0.6189 0.1628 0.023 Uiso 1 1 calc R U . . .
C9 C 0.6078(2) 0.61769(18) 0.3614(2) 0.0188(4) Uani 1 1 d . . . . .
C10 C 0.5729(3) 0.7507(2) 0.3992(3) 0.0232(4) Uani 1 1 d . . . . .
H10A H 0.4534 0.7585 0.3926 0.035 Uiso 1 1 calc R U . . .
H10B H 0.5938 0.8058 0.3181 0.035 Uiso 1 1 calc R U . . .
H10C H 0.6491 0.7727 0.5112 0.035 Uiso 1 1 calc R U . . .
C11 C 1.0306(3) 0.6714(2) 0.3305(3) 0.0328(5) Uani 1 1 d . . . . .
H11 H 1.0792 0.7298 0.2775 0.039 Uiso 1 1 calc R U . . .
C12 C 1.1349(3) 0.5790(2) 0.4210(3) 0.0352(6) Uani 1 1 d . . . . .
H12 H 1.2513 0.5732 0.4287 0.042 Uiso 1 1 calc R U . . .
C13 C 1.0650(3) 0.4950(2) 0.5001(3) 0.0326(5) Uani 1 1 d . . . . .
H13 H 1.1329 0.4301 0.5640 0.039 Uiso 1 1 calc R U . . .
C14 C 0.8944(3) 0.50674(19) 0.4850(3) 0.0250(5) Uani 1 1 d . . . . .
H14 H 0.8442 0.4507 0.5396 0.030 Uiso 1 1 calc R U . . .
C15 C 0.7982(3) 0.60146(19) 0.3893(2) 0.0210(4) Uani 1 1 d . . . . .
O3 O 0.6621(2) 0.62945(15) 0.77329(19) 0.0323(4) Uani 1 1 d D . . . .
H3A H 0.667(4) 0.587(3) 0.863(3) 0.049(8) Uiso 1 1 d D . . . .
H3B H 0.636(4) 0.703(2) 0.789(4) 0.065(10) Uiso 1 1 d D . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.439(2) . ?
O1 H1 0.86(2) . ?
O2 C9 1.433(2) . ?
O2 H2 0.89(2) . ?
N1 C1 1.340(3) . ?
N1 C5 1.347(3) . ?
N2 C11 1.342(3) . ?
N2 C15 1.345(3) . ?
C1 C2 1.384(3) . ?
C1 H1A 0.9500 . ?
C2 C3 1.374(3) . ?
C2 H2A 0.9500 . ?
C3 C4 1.384(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.387(3) . ?
C4 H4 0.9500 . ?
C5 C7 1.533(3) . ?
C6 C7 1.527(3) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.543(3) . ?
C8 C9 1.542(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C15 1.529(3) . ?
C9 C10 1.532(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.378(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.383(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.386(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.386(3) . ?
C14 H14 0.9500 . ?
O3 H3A 0.89(2) . ?
O3 H3B 0.85(2) . ?

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
C7 O1 H1 105(2) . . ?
C9 O2 H2 112(2) . . ?
C1 N1 C5 118.22(18) . . ?
C11 N2 C15 117.1(2) . . ?
N1 C1 C2 123.7(2) . . ?
N1 C1 H1A 118.2 . . ?
C2 C1 H1A 118.2 . . ?
C3 C2 C1 117.7(2) . . ?
C3 C2 H2A 121.1 . . ?
C1 C2 H2A 121.1 . . ?
C2 C3 C4 119.7(2) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 119.3(2) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
N1 C5 C4 121.40(18) . . ?
N1 C5 C7 115.56(17) . . ?
C4 C5 C7 123.03(17) . . ?
C7 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C7 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O1 C7 C6 105.71(15) . . ?
O1 C7 C5 109.70(15) . . ?
C6 C7 C5 109.25(16) . . ?
O1 C7 C8 109.98(16) . . ?
C6 C7 C8 108.85(16) . . ?
C5 C7 C8 113.07(16) . . ?
C9 C8 C7 118.97(15) . . ?
C9 C8 H8A 107.6 . . ?
C7 C8 H8A 107.6 . . ?
C9 C8 H8B 107.6 . . ?
C7 C8 H8B 107.6 . . ?
H8A C8 H8B 107.0 . . ?
O2 C9 C15 110.09(16) . . ?
O2 C9 C10 109.50(15) . . ?
C15 C9 C10 109.80(15) . . ?
O2 C9 C8 107.20(15) . . ?
C15 C9 C8 111.47(15) . . ?
C10 C9 C8 108.74(16) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C11 C12 124.3(2) . . ?
N2 C11 H11 117.9 . . ?
C12 C11 H11 117.9 . . ?
C11 C12 C13 117.9(2) . . ?
C11 C12 H12 121.0 . . ?
C13 C12 H12 121.0 . . ?
C12 C13 C14 119.1(2) . . ?
C12 C13 H13 120.5 . . ?
C14 C13 H13 120.5 . . ?
C15 C14 C13 119.1(2) . . ?
C15 C14 H14 120.5 . . ?
C13 C14 H14 120.5 . . ?
N2 C15 C14 122.52(19) . . ?
N2 C15 C9 115.31(17) . . ?
C14 C15 C9 122.17(18) . . ?
H3A O3 H3B 107(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 -0.1(3) . . . . ?
N1 C1 C2 C3 0.8(4) . . . . ?
C1 C2 C3 C4 -0.5(3) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
C1 N1 C5 C4 -0.9(3) . . . . ?
C1 N1 C5 C7 -179.86(18) . . . . ?
C3 C4 C5 N1 1.2(3) . . . . ?
C3 C4 C5 C7 -179.94(18) . . . . ?
N1 C5 C7 O1 179.32(16) . . . . ?
C4 C5 C7 O1 0.4(2) . . . . ?
N1 C5 C7 C6 63.9(2) . . . . ?
C4 C5 C7 C6 -115.0(2) . . . . ?
N1 C5 C7 C8 -57.5(2) . . . . ?
C4 C5 C7 C8 123.6(2) . . . . ?
O1 C7 C8 C9 57.0(2) . . . . ?
C6 C7 C8 C9 172.35(16) . . . . ?
C5 C7 C8 C9 -66.0(2) . . . . ?
C7 C8 C9 O2 -49.2(2) . . . . ?
C7 C8 C9 C15 71.3(2) . . . . ?
C7 C8 C9 C10 -167.48(17) . . . . ?
C15 N2 C11 C12 0.4(3) . . . . ?
N2 C11 C12 C13 -0.9(3) . . . . ?
C11 C12 C13 C14 0.2(3) . . . . ?
C12 C13 C14 C15 0.8(3) . . . . ?
C11 N2 C15 C14 0.7(3) . . . . ?
C11 N2 C15 C9 -178.40(18) . . . . ?
C13 C14 C15 N2 -1.3(3) . . . . ?
C13 C14 C15 C9 177.70(18) . . . . ?
O2 C9 C15 N2 -171.87(16) . . . . ?
C10 C9 C15 N2 -51.3(2) . . . . ?
C8 C9 C15 N2 69.3(2) . . . . ?
O2 C9 C15 C14 9.1(2) . . . . ?
C10 C9 C15 C14 129.7(2) . . . . ?
C8 C9 C15 C14 -109.8(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O2 0.86(2) 1.82(3) 2.622(2) 154(3) .
O2 H2 O3 0.89(2) 1.78(2) 2.668(2) 174(3) .
O3 H3B O1 0.85(2) 1.95(2) 2.783(2) 166(3) 2_656
O3 H3A N1 0.89(2) 1.91(2) 2.763(2) 160(3) 1_556

_refine_diff_density_max         0.122
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.029

####################################################################### 
# 
# 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_007-16215
_database_code_depnum_ccdc_archive 'CCDC 1529490'
_audit_update_record             
;
2017-01-24 deposited with the CCDC.
2017-06-12 downloaded from the CCDC.
;

_vrf_STRVA01_007-16215           
;
PROBLEM:  Flack test results are ambiguous.
RESPONSE: The material crystallized as an inversion twin.
;


_vrf_PLAT605_007-16215           
;
PROBLEM: LARGE Solvent Accessible VOID(S) in Structure 
RESPONSE: See the "_refine_special_details" and "_platon_squeeze_details"
of the .cif.
;

_vrf_PLAT869_007-16215           
;
PROBLEM: ALERTS Related to the use of SQUEEZE Suppressed  
RESPONSE: See the "_refine_special_details" and "_platon_squeeze_details"
of the .cif.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H32 Cu2 N4 O4'
_chemical_formula_sum            'C30 H32 Cu2 N4 O4'
_chemical_formula_weight         639.67

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'
N N 0.0311 0.0180 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           20
_space_group_name_H-M_alt        'C 2 2 21'
_space_group_name_Hall           'C 2c 2'

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

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

_cell_length_a                   9.7305(7)
_cell_length_b                   20.3710(14)
_cell_length_c                   15.4532(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3063.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    358
_cell_measurement_theta_min      2.9
_cell_measurement_theta_max      68.3

_exptl_crystal_description       Block
_exptl_crystal_colour            Purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_F_000             1320
_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    2.033
_shelx_estimated_absorpt_T_min   0.687
_shelx_estimated_absorpt_T_max   0.905
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.861
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'microfocus rotating anode'
_diffrn_measurement_device_type  'Rigaku Saturn 944+ CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 22.2
_diffrn_reflns_number            53512
_diffrn_reflns_av_unetI/netI     0.0107
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.341
_diffrn_reflns_theta_max         67.898
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2783
_reflns_number_gt                2707
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.769
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    1.000

_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. 
;

_computing_data_collection       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
; 
Dolomanov, O.V.; Bourhis, L.J.; Gildea, R.J.; Howard, J.A.K.; Puschmann, H., 
OLEX2: A complete structure solution, refinement and analysis program 
(2009). J. Appl. Cryst., 42, 339-341. 
;
_computing_publication_material  'CIFTAB-2014/2 (Sheldrick, 2014)'
_refine_special_details          
; 
 Refined as a 2-component inversion twin, the batch scale factor associated
 with the second component refined to a converged value of 0.37(3)

 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 

The hydrogen atoms were first found in the difference map, then generated 
geometrically and refined as riding atoms with C-H distances = 0.95 - 0.99 
angstroms and Uiso(H) = 1.2 times Ueq(C) for CH and CH2 groups and Uiso(H) 
= 1.5 times Ueq(C) for CH3 groups. One reflection was obscured by the beam
stop and subsequently omitted.

The program SQUEEZE was used to compensate for the contribution of disordered 
solvents contained in voids within the crystal lattice from the diffraction 
intensities. This procedure was applied to the data file and the submitted 
model is based on the solvent removed data. Based on the total electron density 
found in the voids (150.6 e/Å³), it is likely that ~15 water molecules 
are present in the unit cell. See "_platon_squeeze_details" in this .cif for 
more information. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0389P)²+2.2192P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     SHELXT
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Refined as an inversion twin. 
;
_refine_ls_abs_structure_Flack   0.37(3)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         2783
_refine_ls_number_parameters     185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0222
_refine_ls_R_factor_gt           0.0216
_refine_ls_wR_factor_ref         0.0597
_refine_ls_wR_factor_gt          0.0594
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.60149(4) 0.28004(2) 0.67706(2) 0.01670(11) Uani 1 1 d . . . . .
O1 O 0.65263(19) 0.19149(9) 0.70147(12) 0.0208(4) Uani 1 1 d . . . . .
O2 O 0.55128(19) 0.36801(9) 0.64939(13) 0.0222(4) Uani 1 1 d . . . . .
N1 N 0.4597(2) 0.23896(10) 0.60453(14) 0.0180(5) Uani 1 1 d . . . . .
N2 N 0.7376(2) 0.32109(10) 0.75360(16) 0.0194(5) Uani 1 1 d . . . . .
C1 C 0.3743(3) 0.27013(13) 0.54952(17) 0.0220(6) Uani 1 1 d . . . . .
H1 H 0.3853 0.3159 0.5404 0.026 Uiso 1 1 calc R U . . .
C2 C 0.2719(3) 0.23742(14) 0.5064(2) 0.0264(6) Uani 1 1 d . . . . .
H2 H 0.2147 0.2599 0.4664 0.032 Uiso 1 1 calc R U . . .
C3 C 0.2532(3) 0.17120(14) 0.52211(19) 0.0271(6) Uani 1 1 d . . . . .
H3 H 0.1808 0.1479 0.4945 0.032 Uiso 1 1 calc R U . . .
C4 C 0.3409(3) 0.13931(14) 0.57846(19) 0.0256(6) Uani 1 1 d . . . . .
H4 H 0.3298 0.0938 0.5896 0.031 Uiso 1 1 calc R U . . .
C5 C 0.4457(3) 0.17450(12) 0.61878(17) 0.0189(5) Uani 1 1 d . . . . .
C6 C 0.5592(3) 0.14328(12) 0.6727(2) 0.0200(5) Uani 1 1 d . . . . .
C7 C 0.6337(3) 0.09445(13) 0.61283(19) 0.0241(6) Uani 1 1 d . . . . .
H7A H 0.6648 0.1173 0.5606 0.036 Uiso 1 1 calc R U . . .
H7B H 0.5706 0.0590 0.5967 0.036 Uiso 1 1 calc R U . . .
H7C H 0.7132 0.0759 0.6431 0.036 Uiso 1 1 calc R U . . .
C8 C 0.5000 0.10415(17) 0.7500 0.0197(8) Uani 1 2 d S T P . .
H8A H 0.4262 0.0753 0.7276 0.024 Uiso 0.5 1 calc R U P . .
H8B H 0.5738 0.0753 0.7724 0.024 Uiso 0.5 1 calc R U P . .
C9 C 0.8368(3) 0.29070(14) 0.79817(17) 0.0240(6) Uani 1 1 d . . . . .
H9 H 0.8492 0.2448 0.7908 0.029 Uiso 1 1 calc R U . . .
C10 C 0.9218(3) 0.32405(14) 0.85450(19) 0.0270(6) Uani 1 1 d . . . . .
H10 H 0.9934 0.3019 0.8844 0.032 Uiso 1 1 calc R U . . .
C11 C 0.9000(3) 0.39031(15) 0.8662(2) 0.0313(6) Uani 1 1 d . . . . .
H11 H 0.9561 0.4144 0.9053 0.038 Uiso 1 1 calc R U . . .
C12 C 0.7969(3) 0.42152(13) 0.8213(2) 0.0305(6) Uani 1 1 d . . . . .
H12 H 0.7808 0.4671 0.8297 0.037 Uiso 1 1 calc R U . . .
C13 C 0.7160(3) 0.38600(13) 0.76318(19) 0.0226(6) Uani 1 1 d . . . . .
C14 C 0.6107(3) 0.41635(12) 0.70155(18) 0.0240(6) Uani 1 1 d . . . . .
C15 C 0.5000 0.45635(19) 0.7500 0.0269(9) Uani 1 2 d S T P . .
H15B H 0.5468 0.4851 0.7924 0.032 Uiso 0.5 1 calc R U P . .
H15A H 0.4532 0.4851 0.7076 0.032 Uiso 0.5 1 calc R U P . .
C16 C 0.6936(3) 0.46499(13) 0.6446(2) 0.0286(6) Uani 1 1 d . . . . .
H16A H 0.7683 0.4415 0.6155 0.043 Uiso 1 1 calc R U . . .
H16B H 0.7321 0.4997 0.6811 0.043 Uiso 1 1 calc R U . . .
H16C H 0.6326 0.4845 0.6011 0.043 Uiso 1 1 calc 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
Cu1 O2 1.9059(18) . ?
Cu1 O1 1.9090(18) . ?
Cu1 N2 1.963(2) . ?
Cu1 N1 1.964(2) . ?
Cu1 Cu1 2.9971(8) 3_656 ?
O1 C6 1.411(3) . ?
O2 C14 1.398(3) . ?
N1 C5 1.339(3) . ?
N1 C1 1.348(3) . ?
N2 C9 1.338(4) . ?
N2 C13 1.347(3) . ?
C1 C2 1.371(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.383(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.382(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.393(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.522(4) . ?
C6 C7 1.540(4) . ?
C6 C8 1.547(3) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C6 1.547(3) 3_656 ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.379(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.378(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.376(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.396(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.529(4) . ?
C14 C15 1.544(3) . ?
C14 C16 1.552(4) . ?
C15 C14 1.544(3) 3_656 ?
C15 H15B 0.9900 . ?
C15 H15A 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Cu1 O1 178.43(9) . . ?
O2 Cu1 N2 84.70(9) . . ?
O1 Cu1 N2 96.18(8) . . ?
O2 Cu1 N1 95.31(8) . . ?
O1 Cu1 N1 83.87(8) . . ?
N2 Cu1 N1 177.58(9) . . ?
O2 Cu1 Cu1 89.99(6) . 3_656 ?
O1 Cu1 Cu1 91.33(6) . 3_656 ?
N2 Cu1 Cu1 89.51(7) . 3_656 ?
N1 Cu1 Cu1 88.07(6) . 3_656 ?
C6 O1 Cu1 115.31(15) . . ?
C14 O2 Cu1 115.28(16) . . ?
C5 N1 C1 120.2(2) . . ?
C5 N1 Cu1 113.32(18) . . ?
C1 N1 Cu1 126.31(17) . . ?
C9 N2 C13 120.7(2) . . ?
C9 N2 Cu1 126.88(18) . . ?
C13 N2 Cu1 112.26(19) . . ?
N1 C1 C2 121.7(2) . . ?
N1 C1 H1 119.1 . . ?
C2 C1 H1 119.1 . . ?
C1 C2 C3 119.0(3) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C4 C3 C2 119.2(3) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 119.5(3) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
N1 C5 C4 120.4(2) . . ?
N1 C5 C6 115.2(2) . . ?
C4 C5 C6 124.1(2) . . ?
O1 C6 C5 110.45(19) . . ?
O1 C6 C7 109.6(2) . . ?
C5 C6 C7 106.4(2) . . ?
O1 C6 C8 110.8(2) . . ?
C5 C6 C8 111.59(19) . . ?
C7 C6 C8 107.8(2) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 C6 118.0(3) 3_656 . ?
C6 C8 H8A 107.8 3_656 . ?
C6 C8 H8A 107.8 . . ?
C6 C8 H8B 107.8 3_656 . ?
C6 C8 H8B 107.8 . . ?
H8A C8 H8B 107.1 . . ?
N2 C9 C10 122.0(3) . . ?
N2 C9 H9 119.0 . . ?
C10 C9 H9 119.0 . . ?
C11 C10 C9 118.2(3) . . ?
C11 C10 H10 120.9 . . ?
C9 C10 H10 120.9 . . ?
C12 C11 C10 119.9(3) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C11 C12 C13 119.8(3) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
N2 C13 C12 119.4(3) . . ?
N2 C13 C14 115.7(2) . . ?
C12 C13 C14 124.7(2) . . ?
O2 C14 C13 110.6(2) . . ?
O2 C14 C15 111.3(2) . . ?
C13 C14 C15 112.2(2) . . ?
O2 C14 C16 109.7(2) . . ?
C13 C14 C16 105.3(2) . . ?
C15 C14 C16 107.5(2) . . ?
C14 C15 C14 116.3(3) 3_656 . ?
C14 C15 H15B 108.2 3_656 . ?
C14 C15 H15B 108.2 . . ?
C14 C15 H15A 108.2 3_656 . ?
C14 C15 H15A 108.2 . . ?
H15B C15 H15A 107.4 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
C5 N1 C1 C2 -0.3(4) . . . . ?
Cu1 N1 C1 C2 -175.1(2) . . . . ?
N1 C1 C2 C3 2.2(4) . . . . ?
C1 C2 C3 C4 -2.2(4) . . . . ?
C2 C3 C4 C5 0.5(4) . . . . ?
C1 N1 C5 C4 -1.5(4) . . . . ?
Cu1 N1 C5 C4 174.0(2) . . . . ?
C1 N1 C5 C6 172.3(2) . . . . ?
Cu1 N1 C5 C6 -12.2(3) . . . . ?
C3 C4 C5 N1 1.4(4) . . . . ?
C3 C4 C5 C6 -171.8(3) . . . . ?
Cu1 O1 C6 C5 6.6(3) . . . . ?
Cu1 O1 C6 C7 123.59(18) . . . . ?
Cu1 O1 C6 C8 -117.53(18) . . . . ?
N1 C5 C6 O1 3.9(3) . . . . ?
C4 C5 C6 O1 177.4(3) . . . . ?
N1 C5 C6 C7 -115.0(2) . . . . ?
C4 C5 C6 C7 58.5(3) . . . . ?
N1 C5 C6 C8 127.6(2) . . . . ?
C4 C5 C6 C8 -58.9(3) . . . . ?
O1 C6 C8 C6 50.16(14) . . . 3_656 ?
C5 C6 C8 C6 -73.36(17) . . . 3_656 ?
C7 C6 C8 C6 170.1(2) . . . 3_656 ?
C13 N2 C9 C10 -0.9(4) . . . . ?
Cu1 N2 C9 C10 -175.8(2) . . . . ?
N2 C9 C10 C11 1.8(4) . . . . ?
C9 C10 C11 C12 -0.9(4) . . . . ?
C10 C11 C12 C13 -0.8(5) . . . . ?
C9 N2 C13 C12 -0.9(4) . . . . ?
Cu1 N2 C13 C12 174.7(2) . . . . ?
C9 N2 C13 C14 173.5(2) . . . . ?
Cu1 N2 C13 C14 -10.9(3) . . . . ?
C11 C12 C13 N2 1.7(5) . . . . ?
C11 C12 C13 C14 -172.1(3) . . . . ?
Cu1 O2 C14 C13 6.2(3) . . . . ?
Cu1 O2 C14 C15 -119.21(19) . . . . ?
Cu1 O2 C14 C16 122.0(2) . . . . ?
N2 C13 C14 O2 3.4(3) . . . . ?
C12 C13 C14 O2 177.4(3) . . . . ?
N2 C13 C14 C15 128.2(3) . . . . ?
C12 C13 C14 C15 -57.7(4) . . . . ?
N2 C13 C14 C16 -115.1(3) . . . . ?
C12 C13 C14 C16 59.0(4) . . . . ?
O2 C14 C15 C14 49.59(15) . . . 3_656 ?
C13 C14 C15 C14 -74.92(18) . . . 3_656 ?
C16 C14 C15 C14 169.8(2) . . . 3_656 ?

_refine_diff_density_max         0.231
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.048



####################################################################### 
# 
# 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_mini-14056
_database_code_depnum_ccdc_archive 'CCDC 1529487'
_audit_update_record             
;
2017-01-24 deposited with the CCDC.
2017-06-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C31 H32 Co2 N4 O7, 2(H2 O)'
_chemical_formula_sum            'C31 H36 Co2 N4 O9'
_chemical_formula_weight         726.50

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   8.267(4)
_cell_length_b                   14.974(8)
_cell_length_c                   12.165(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.544(12)
_cell_angle_gamma                90
_cell_volume                     1505.4(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    6837
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      28.9

_exptl_crystal_description       Block
_exptl_crystal_colour            Black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.603
_exptl_crystal_F_000             752
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.400
_exptl_absorpt_coefficient_mu    1.165
_shelx_estimated_absorpt_T_min   0.653
_shelx_estimated_absorpt_T_max   0.653
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.502
_exptl_absorpt_correction_T_max  0.653
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private Communication'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Tube'
_diffrn_measurement_device_type  'Rigaku Mercury275R CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 6.8
_diffrn_reflns_number            17486
_diffrn_reflns_av_unetI/netI     0.0588
_diffrn_reflns_av_R_equivalents  0.0517
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.017
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6131
_reflns_number_gt                5432
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.924
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_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       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    
; 
 NAME HERE 
 The Department of Chemistry 
 Yale University 
 P. O. Box 208107 
 New Haven 
 Connecticut 06520 USA. 
;
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_refine_special_details          
; 
 Refined as a 2-component inversion twin. 

 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 

 The hydrogen atoms were first found in the difference map, then generated 
 geometrically and refined as riding atoms with C-H distances = 0.95- 0.99 
 Å and Uiso(H) = 1.2 times Ueq(C) for CH and CH2 groups and Uiso(H) 
 = 1.5 times Ueq(C) for CH3 groups. The hydrogen atoms on the water
 were suggested by the difference map, and refined as geometrically
 fixed positions riding on their associated oxygen atoms.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0316P)²+0.2804P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Refined as an inversion twin. 
;
_refine_ls_abs_structure_Flack   0.453(18)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         6131
_refine_ls_number_parameters     426
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0450
_refine_ls_wR_factor_ref         0.0810
_refine_ls_wR_factor_gt          0.0778
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.24958(8) 0.50409(5) 0.26945(6) 0.02507(18) Uani 1 1 d . . . . .
Co2 Co 0.21065(8) 0.69473(4) 0.22857(6) 0.02429(18) Uani 1 1 d . . . . .
O1 O 0.4216(5) 0.4382(2) 0.3297(3) 0.0310(9) Uani 1 1 d . . . . .
O2 O 0.3786(4) 0.6131(2) 0.2754(3) 0.0226(9) Uani 1 1 d . . . . .
O3 O 0.3193(4) 0.8066(2) 0.2200(3) 0.0301(9) Uani 1 1 d . . . . .
O4 O 0.1118(5) 0.4064(2) 0.2445(3) 0.0289(10) Uani 1 1 d . . . . .
O5 O 0.0799(4) 0.5887(3) 0.2218(3) 0.0246(9) Uani 1 1 d . . . . .
O6 O 0.0620(5) 0.7893(3) 0.1931(3) 0.0317(10) Uani 1 1 d . . . . .
O7 O 0.1663(5) 0.9283(3) 0.1806(4) 0.0419(11) Uani 1 1 d . . . . .
N1 N 0.1769(5) 0.5064(3) 0.4176(3) 0.0273(10) Uani 1 1 d . . . . .
N2 N 0.1890(5) 0.7115(3) 0.3827(3) 0.0244(10) Uani 1 1 d . . . . .
N3 N 0.3264(5) 0.4733(3) 0.1270(4) 0.0268(11) Uani 1 1 d . . . . .
N4 N 0.2349(5) 0.6688(3) 0.0760(3) 0.0245(10) Uani 1 1 d . . . . .
C1 C 0.0239(6) 0.5188(4) 0.4493(4) 0.0334(13) Uani 1 1 d . . . . .
H1 H -0.0557 0.5374 0.3976 0.040 Uiso 1 1 calc R U . . .
C2 C -0.0169(7) 0.5046(4) 0.5566(4) 0.0419(14) Uani 1 1 d . . . . .
H2 H -0.1233 0.5147 0.5791 0.050 Uiso 1 1 calc R U . . .
C3 C 0.0994(8) 0.4756(4) 0.6302(5) 0.0445(17) Uani 1 1 d . . . . .
H3 H 0.0722 0.4644 0.7034 0.053 Uiso 1 1 calc R U . . .
C4 C 0.2557(8) 0.4628(4) 0.5982(5) 0.0414(15) Uani 1 1 d . . . . .
H4 H 0.3359 0.4434 0.6489 0.050 Uiso 1 1 calc R U . . .
C5 C 0.2929(7) 0.4790(3) 0.4901(4) 0.0297(13) Uani 1 1 d . . . . .
C6 C 0.4549(7) 0.4699(4) 0.4363(4) 0.0310(13) Uani 1 1 d . . . . .
C7 C 0.5389(7) 0.5617(4) 0.4329(5) 0.0303(13) Uani 1 1 d . . . . .
H7A H 0.5658 0.5790 0.5089 0.036 Uiso 1 1 calc R U . . .
H7B H 0.6415 0.5538 0.3955 0.036 Uiso 1 1 calc R U . . .
C8 C 0.4510(6) 0.6401(4) 0.3785(4) 0.0259(13) Uani 1 1 d . . . . .
C9 C 0.3154(6) 0.6808(3) 0.4457(4) 0.0256(12) Uani 1 1 d . . . . .
C10 C 0.3155(7) 0.6895(4) 0.5572(4) 0.0347(13) Uani 1 1 d . . . . .
H10 H 0.4025 0.6677 0.6008 0.042 Uiso 1 1 calc R U . . .
C11 C 0.1861(8) 0.7307(4) 0.6050(5) 0.0433(16) Uani 1 1 d . . . . .
H11 H 0.1853 0.7382 0.6817 0.052 Uiso 1 1 calc R U . . .
C12 C 0.0580(8) 0.7608(4) 0.5410(5) 0.0433(17) Uani 1 1 d . . . . .
H12 H -0.0315 0.7882 0.5730 0.052 Uiso 1 1 calc R U . . .
C13 C 0.0639(7) 0.7501(4) 0.4294(5) 0.0331(14) Uani 1 1 d . . . . .
H13 H -0.0230 0.7706 0.3848 0.040 Uiso 1 1 calc R U . . .
C14 C 0.5679(7) 0.4054(4) 0.4963(5) 0.0420(15) Uani 1 1 d . . . . .
H14A H 0.5164 0.3473 0.5009 0.063 Uiso 1 1 calc R U . . .
H14B H 0.5918 0.4276 0.5699 0.063 Uiso 1 1 calc R U . . .
H14C H 0.6676 0.3999 0.4566 0.063 Uiso 1 1 calc R U . . .
C15 C 0.5800(6) 0.7111(4) 0.3592(5) 0.0346(14) Uani 1 1 d . . . . .
H15A H 0.6569 0.6889 0.3070 0.052 Uiso 1 1 calc R U . . .
H15B H 0.6360 0.7248 0.4283 0.052 Uiso 1 1 calc R U . . .
H15C H 0.5288 0.7648 0.3302 0.052 Uiso 1 1 calc R U . . .
C16 C 0.4711(6) 0.4926(4) 0.0875(4) 0.0309(13) Uani 1 1 d . . . . .
H16 H 0.5418 0.5297 0.1284 0.037 Uiso 1 1 calc R U . . .
C17 C 0.5193(7) 0.4595(4) -0.0115(5) 0.0387(15) Uani 1 1 d . . . . .
H17 H 0.6214 0.4740 -0.0388 0.046 Uiso 1 1 calc R U . . .
C18 C 0.4151(8) 0.4045(4) -0.0701(5) 0.0380(15) Uani 1 1 d . . . . .
H18 H 0.4452 0.3816 -0.1385 0.046 Uiso 1 1 calc R U . . .
C19 C 0.2675(7) 0.3832(4) -0.0288(4) 0.0358(14) Uani 1 1 d . . . . .
H19 H 0.1956 0.3457 -0.0682 0.043 Uiso 1 1 calc R U . . .
C20 C 0.2264(7) 0.4179(3) 0.0717(4) 0.0266(12) Uani 1 1 d . . . . .
C21 C 0.0711(7) 0.4047(4) 0.1318(5) 0.0301(13) Uani 1 1 d . . . . .
C22 C -0.0486(6) 0.4796(3) 0.1006(5) 0.0296(13) Uani 1 1 d . . . . .
H22A H -0.0809 0.4714 0.0232 0.035 Uiso 1 1 calc R U . . .
H22B H -0.1457 0.4711 0.1439 0.035 Uiso 1 1 calc R U . . .
C23 C 0.0061(7) 0.5769(4) 0.1154(5) 0.0264(13) Uani 1 1 d . . . . .
C24 C 0.1287(6) 0.6097(3) 0.0332(4) 0.0247(12) Uani 1 1 d . . . . .
C25 C 0.1327(7) 0.5853(4) -0.0760(5) 0.0350(14) Uani 1 1 d . . . . .
H25 H 0.0534 0.5475 -0.1075 0.042 Uiso 1 1 calc R U . . .
C26 C 0.2579(7) 0.6186(4) -0.1378(5) 0.0386(15) Uani 1 1 d . . . . .
H26 H 0.2672 0.6008 -0.2115 0.046 Uiso 1 1 calc R U . . .
C27 C 0.3683(7) 0.6772(4) -0.0923(4) 0.0359(14) Uani 1 1 d . . . . .
H27 H 0.4525 0.7006 -0.1341 0.043 Uiso 1 1 calc R U . . .
C28 C 0.3526(6) 0.7009(4) 0.0157(4) 0.0316(12) Uani 1 1 d . . . . .
H28 H 0.4274 0.7410 0.0479 0.038 Uiso 1 1 calc R U . . .
C29 C -0.0086(7) 0.3157(4) 0.1048(5) 0.0429(15) Uani 1 1 d . . . . .
H29A H 0.0624 0.2675 0.1285 0.064 Uiso 1 1 calc R U . . .
H29B H -0.0291 0.3116 0.0261 0.064 Uiso 1 1 calc R U . . .
H29C H -0.1102 0.3113 0.1426 0.064 Uiso 1 1 calc R U . . .
C30 C -0.1456(6) 0.6354(4) 0.1041(5) 0.0380(14) Uani 1 1 d . . . . .
H30A H -0.2212 0.6191 0.1603 0.057 Uiso 1 1 calc R U . . .
H30B H -0.1961 0.6264 0.0320 0.057 Uiso 1 1 calc R U . . .
H30C H -0.1156 0.6977 0.1128 0.057 Uiso 1 1 calc R U . . .
C31 C 0.1801(7) 0.8480(4) 0.1964(4) 0.0304(13) Uani 1 1 d . . . . .
O8 O 0.3250(7) 0.2625(3) 0.2905(6) 0.0759(17) Uani 1 1 d G . . . .
H8A H 0.2411 0.2944 0.2798 0.114 Uiso 1 1 d G U . . .
H8B H 0.4023 0.2953 0.3141 0.114 Uiso 1 1 d G U . . .
O9 O 0.3732(7) 0.0715(4) 0.2802(5) 0.0773(17) Uani 1 1 d G . . . .
H9A H 0.3194 0.0415 0.2322 0.116 Uiso 1 1 d G U . . .
H9B H 0.3420 0.1256 0.2787 0.116 Uiso 1 1 d G 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 O1 1.864(4) . ?
Co1 O4 1.874(4) . ?
Co1 N1 1.916(4) . ?
Co1 N3 1.917(4) . ?
Co1 O2 1.950(4) . ?
Co1 O5 1.966(4) . ?
Co1 Co2 2.9140(17) . ?
Co2 N2 1.905(4) . ?
Co2 O3 1.905(4) . ?
Co2 N4 1.912(4) . ?
Co2 O6 1.917(4) . ?
Co2 O5 1.921(4) . ?
Co2 O2 1.925(4) . ?
Co2 C31 2.341(6) . ?
O1 C6 1.401(6) . ?
O2 C8 1.433(6) . ?
O3 C31 1.331(7) . ?
O4 C21 1.403(7) . ?
O5 C23 1.427(6) . ?
O6 C31 1.314(7) . ?
O7 C31 1.222(7) . ?
N1 C1 1.345(6) . ?
N1 C5 1.349(7) . ?
N2 C13 1.326(6) . ?
N2 C9 1.359(7) . ?
N3 C16 1.333(6) . ?
N3 C20 1.339(6) . ?
N4 C28 1.324(6) . ?
N4 C24 1.341(6) . ?
C1 C2 1.374(7) . ?
C1 H1 0.9400 . ?
C2 C3 1.367(8) . ?
C2 H2 0.9400 . ?
C3 C4 1.373(8) . ?
C3 H3 0.9400 . ?
C4 C5 1.380(8) . ?
C4 H4 0.9400 . ?
C5 C6 1.513(8) . ?
C6 C14 1.518(7) . ?
C6 C7 1.542(7) . ?
C7 C8 1.522(7) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C8 C15 1.529(7) . ?
C8 C9 1.532(7) . ?
C9 C10 1.363(7) . ?
C10 C11 1.377(8) . ?
C10 H10 0.9400 . ?
C11 C12 1.373(8) . ?
C11 H11 0.9400 . ?
C12 C13 1.369(8) . ?
C12 H12 0.9400 . ?
C13 H13 0.9400 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 H14C 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 H15C 0.9700 . ?
C16 C17 1.371(8) . ?
C16 H16 0.9400 . ?
C17 C18 1.376(9) . ?
C17 H17 0.9400 . ?
C18 C19 1.370(8) . ?
C18 H18 0.9400 . ?
C19 C20 1.379(7) . ?
C19 H19 0.9400 . ?
C20 C21 1.508(7) . ?
C21 C29 1.519(8) . ?
C21 C22 1.536(8) . ?
C22 C23 1.534(7) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C23 C24 1.524(7) . ?
C23 C30 1.533(7) . ?
C24 C25 1.380(7) . ?
C25 C26 1.388(8) . ?
C25 H25 0.9400 . ?
C26 C27 1.373(8) . ?
C26 H26 0.9400 . ?
C27 C28 1.370(7) . ?
C27 H27 0.9400 . ?
C28 H28 0.9400 . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C29 H29C 0.9700 . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C30 H30C 0.9700 . ?
O8 H8A 0.8491 . ?
O8 H8B 0.8498 . ?
O9 H9A 0.8519 . ?
O9 H9B 0.8503 . ?

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 96.01(17) . . ?
O1 Co1 N1 83.97(18) . . ?
O4 Co1 N1 87.80(18) . . ?
O1 Co1 N3 87.72(18) . . ?
O4 Co1 N3 83.14(17) . . ?
N1 Co1 N3 167.0(2) . . ?
O1 Co1 O2 90.99(17) . . ?
O4 Co1 O2 171.49(16) . . ?
N1 Co1 O2 97.78(17) . . ?
N3 Co1 O2 92.33(17) . . ?
O1 Co1 O5 170.90(17) . . ?
O4 Co1 O5 91.70(17) . . ?
N1 Co1 O5 91.52(17) . . ?
N3 Co1 O5 98.03(17) . . ?
O2 Co1 O5 81.77(16) . . ?
O1 Co1 Co2 131.67(12) . . ?
O4 Co1 Co2 132.32(13) . . ?
N1 Co1 Co2 96.16(15) . . ?
N3 Co1 Co2 96.84(14) . . ?
O2 Co1 Co2 40.92(11) . . ?
O5 Co1 Co2 40.86(11) . . ?
N2 Co2 O3 89.72(17) . . ?
N2 Co2 N4 175.78(18) . . ?
O3 Co2 N4 93.65(16) . . ?
N2 Co2 O6 92.74(18) . . ?
O3 Co2 O6 68.79(16) . . ?
N4 Co2 O6 90.85(17) . . ?
N2 Co2 O5 94.76(17) . . ?
O3 Co2 O5 171.86(18) . . ?
N4 Co2 O5 82.20(17) . . ?
O6 Co2 O5 104.15(16) . . ?
N2 Co2 O2 83.01(17) . . ?
O3 Co2 O2 103.74(16) . . ?
N4 Co2 O2 93.71(16) . . ?
O6 Co2 O2 171.52(17) . . ?
O5 Co2 O2 83.58(17) . . ?
N2 Co2 C31 91.31(18) . . ?
O3 Co2 C31 34.65(18) . . ?
N4 Co2 C31 92.91(17) . . ?
O6 Co2 C31 34.14(18) . . ?
O5 Co2 C31 138.18(19) . . ?
O2 Co2 C31 138.23(18) . . ?
N2 Co2 Co1 88.49(14) . . ?
O3 Co2 Co1 145.17(12) . . ?
N4 Co2 Co1 87.29(12) . . ?
O6 Co2 Co1 146.04(12) . . ?
O5 Co2 Co1 42.02(12) . . ?
O2 Co2 Co1 41.56(10) . . ?
C31 Co2 Co1 179.74(16) . . ?
C6 O1 Co1 108.3(3) . . ?
C8 O2 Co2 111.1(3) . . ?
C8 O2 Co1 118.9(3) . . ?
Co2 O2 Co1 97.52(16) . . ?
C31 O3 Co2 90.9(3) . . ?
C21 O4 Co1 107.5(3) . . ?
C23 O5 Co2 111.6(3) . . ?
C23 O5 Co1 118.1(3) . . ?
Co2 O5 Co1 97.12(17) . . ?
C31 O6 Co2 90.9(3) . . ?
C1 N1 C5 120.9(5) . . ?
C1 N1 Co1 126.4(4) . . ?
C5 N1 Co1 112.0(4) . . ?
C13 N2 C9 120.2(5) . . ?
C13 N2 Co2 125.0(4) . . ?
C9 N2 Co2 114.8(3) . . ?
C16 N3 C20 120.0(5) . . ?
C16 N3 Co1 126.6(4) . . ?
C20 N3 Co1 112.8(4) . . ?
C28 N4 C24 120.5(5) . . ?
C28 N4 Co2 124.1(4) . . ?
C24 N4 Co2 115.2(3) . . ?
N1 C1 C2 120.5(5) . . ?
N1 C1 H1 119.7 . . ?
C2 C1 H1 119.7 . . ?
C3 C2 C1 119.0(5) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 120.6(6) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C3 C4 C5 118.8(6) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
N1 C5 C4 120.2(5) . . ?
N1 C5 C6 111.5(4) . . ?
C4 C5 C6 128.3(5) . . ?
O1 C6 C5 106.1(4) . . ?
O1 C6 C14 109.5(4) . . ?
C5 C6 C14 112.9(5) . . ?
O1 C6 C7 110.8(4) . . ?
C5 C6 C7 109.6(4) . . ?
C14 C6 C7 108.0(4) . . ?
C8 C7 C6 119.3(4) . . ?
C8 C7 H7A 107.5 . . ?
C6 C7 H7A 107.5 . . ?
C8 C7 H7B 107.5 . . ?
C6 C7 H7B 107.5 . . ?
H7A C7 H7B 107.0 . . ?
O2 C8 C7 110.2(4) . . ?
O2 C8 C15 109.8(4) . . ?
C7 C8 C15 106.1(4) . . ?
O2 C8 C9 106.6(4) . . ?
C7 C8 C9 115.0(5) . . ?
C15 C8 C9 109.1(4) . . ?
N2 C9 C10 120.6(5) . . ?
N2 C9 C8 113.4(4) . . ?
C10 C9 C8 126.0(5) . . ?
C9 C10 C11 118.9(5) . . ?
C9 C10 H10 120.6 . . ?
C11 C10 H10 120.6 . . ?
C12 C11 C10 120.3(6) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C13 C12 C11 118.4(6) . . ?
C13 C12 H12 120.8 . . ?
C11 C12 H12 120.8 . . ?
N2 C13 C12 121.7(5) . . ?
N2 C13 H13 119.2 . . ?
C12 C13 H13 119.2 . . ?
C6 C14 H14A 109.5 . . ?
C6 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C6 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C8 C15 H15A 109.5 . . ?
C8 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C8 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N3 C16 C17 121.6(5) . . ?
N3 C16 H16 119.2 . . ?
C17 C16 H16 119.2 . . ?
C16 C17 C18 118.5(5) . . ?
C16 C17 H17 120.7 . . ?
C18 C17 H17 120.7 . . ?
C19 C18 C17 120.1(5) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C20 118.7(5) . . ?
C18 C19 H19 120.6 . . ?
C20 C19 H19 120.6 . . ?
N3 C20 C19 121.0(5) . . ?
N3 C20 C21 111.1(4) . . ?
C19 C20 C21 127.9(5) . . ?
O4 C21 C20 106.7(5) . . ?
O4 C21 C29 108.6(5) . . ?
C20 C21 C29 112.3(5) . . ?
O4 C21 C22 111.4(5) . . ?
C20 C21 C22 109.6(4) . . ?
C29 C21 C22 108.3(5) . . ?
C23 C22 C21 118.5(4) . . ?
C23 C22 H22A 107.7 . . ?
C21 C22 H22A 107.7 . . ?
C23 C22 H22B 107.7 . . ?
C21 C22 H22B 107.7 . . ?
H22A C22 H22B 107.1 . . ?
O5 C23 C24 106.2(4) . . ?
O5 C23 C30 109.8(4) . . ?
C24 C23 C30 108.3(5) . . ?
O5 C23 C22 110.0(5) . . ?
C24 C23 C22 115.4(5) . . ?
C30 C23 C22 107.1(4) . . ?
N4 C24 C25 121.1(5) . . ?
N4 C24 C23 113.5(5) . . ?
C25 C24 C23 125.4(5) . . ?
C24 C25 C26 117.7(5) . . ?
C24 C25 H25 121.2 . . ?
C26 C25 H25 121.2 . . ?
C27 C26 C25 120.6(5) . . ?
C27 C26 H26 119.7 . . ?
C25 C26 H26 119.7 . . ?
C28 C27 C26 118.2(5) . . ?
C28 C27 H27 120.9 . . ?
C26 C27 H27 120.9 . . ?
N4 C28 C27 121.8(5) . . ?
N4 C28 H28 119.1 . . ?
C27 C28 H28 119.1 . . ?
C21 C29 H29A 109.5 . . ?
C21 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C21 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C23 C30 H30A 109.5 . . ?
C23 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C23 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
O7 C31 O6 125.9(6) . . ?
O7 C31 O3 124.7(6) . . ?
O6 C31 O3 109.4(5) . . ?
O7 C31 Co2 179.0(5) . . ?
O6 C31 Co2 55.0(3) . . ?
O3 C31 Co2 54.5(3) . . ?
H8A O8 H8B 109.3 . . ?
H9A O9 H9B 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
O4 Co1 O1 C6 -120.9(3) . . . . ?
N1 Co1 O1 C6 -33.8(4) . . . . ?
N3 Co1 O1 C6 156.3(4) . . . . ?
O2 Co1 O1 C6 64.0(3) . . . . ?
Co2 Co1 O1 C6 59.1(4) . . . . ?
O1 Co1 O4 C21 -122.1(4) . . . . ?
N1 Co1 O4 C21 154.2(4) . . . . ?
N3 Co1 O4 C21 -35.1(3) . . . . ?
O5 Co1 O4 C21 62.8(3) . . . . ?
Co2 Co1 O4 C21 57.9(4) . . . . ?
C5 N1 C1 C2 0.6(9) . . . . ?
Co1 N1 C1 C2 169.3(4) . . . . ?
N1 C1 C2 C3 -1.5(9) . . . . ?
C1 C2 C3 C4 1.5(10) . . . . ?
C2 C3 C4 C5 -0.6(9) . . . . ?
C1 N1 C5 C4 0.3(8) . . . . ?
Co1 N1 C5 C4 -169.9(4) . . . . ?
C1 N1 C5 C6 -179.8(5) . . . . ?
Co1 N1 C5 C6 10.0(5) . . . . ?
C3 C4 C5 N1 -0.4(9) . . . . ?
C3 C4 C5 C6 179.8(5) . . . . ?
Co1 O1 C6 C5 45.5(5) . . . . ?
Co1 O1 C6 C14 167.6(4) . . . . ?
Co1 O1 C6 C7 -73.3(4) . . . . ?
N1 C5 C6 O1 -36.1(6) . . . . ?
C4 C5 C6 O1 143.7(6) . . . . ?
N1 C5 C6 C14 -156.0(5) . . . . ?
C4 C5 C6 C14 23.8(8) . . . . ?
N1 C5 C6 C7 83.5(5) . . . . ?
C4 C5 C6 C7 -96.7(7) . . . . ?
O1 C6 C7 C8 61.0(6) . . . . ?
C5 C6 C7 C8 -55.7(6) . . . . ?
C14 C6 C7 C8 -179.1(5) . . . . ?
Co2 O2 C8 C7 160.7(3) . . . . ?
Co1 O2 C8 C7 48.7(5) . . . . ?
Co2 O2 C8 C15 -82.8(4) . . . . ?
Co1 O2 C8 C15 165.2(3) . . . . ?
Co2 O2 C8 C9 35.2(4) . . . . ?
Co1 O2 C8 C9 -76.7(4) . . . . ?
C6 C7 C8 O2 -45.3(6) . . . . ?
C6 C7 C8 C15 -164.1(5) . . . . ?
C6 C7 C8 C9 75.2(6) . . . . ?
C13 N2 C9 C10 -0.1(8) . . . . ?
Co2 N2 C9 C10 179.4(4) . . . . ?
C13 N2 C9 C8 -178.7(5) . . . . ?
Co2 N2 C9 C8 0.8(5) . . . . ?
O2 C8 C9 N2 -23.4(6) . . . . ?
C7 C8 C9 N2 -145.9(5) . . . . ?
C15 C8 C9 N2 95.1(5) . . . . ?
O2 C8 C9 C10 158.1(5) . . . . ?
C7 C8 C9 C10 35.6(7) . . . . ?
C15 C8 C9 C10 -83.4(7) . . . . ?
N2 C9 C10 C11 -0.7(8) . . . . ?
C8 C9 C10 C11 177.7(5) . . . . ?
C9 C10 C11 C12 1.2(9) . . . . ?
C10 C11 C12 C13 -1.0(9) . . . . ?
C9 N2 C13 C12 0.4(9) . . . . ?
Co2 N2 C13 C12 -179.1(5) . . . . ?
C11 C12 C13 N2 0.1(9) . . . . ?
C20 N3 C16 C17 2.4(8) . . . . ?
Co1 N3 C16 C17 173.3(4) . . . . ?
N3 C16 C17 C18 -0.6(9) . . . . ?
C16 C17 C18 C19 -0.7(9) . . . . ?
C17 C18 C19 C20 0.1(9) . . . . ?
C16 N3 C20 C19 -3.0(8) . . . . ?
Co1 N3 C20 C19 -175.1(4) . . . . ?
C16 N3 C20 C21 179.3(5) . . . . ?
Co1 N3 C20 C21 7.2(5) . . . . ?
C18 C19 C20 N3 1.8(8) . . . . ?
C18 C19 C20 C21 179.1(5) . . . . ?
Co1 O4 C21 C20 46.2(5) . . . . ?
Co1 O4 C21 C29 167.5(4) . . . . ?
Co1 O4 C21 C22 -73.3(4) . . . . ?
N3 C20 C21 O4 -34.8(6) . . . . ?
C19 C20 C21 O4 147.6(5) . . . . ?
N3 C20 C21 C29 -153.7(5) . . . . ?
C19 C20 C21 C29 28.7(8) . . . . ?
N3 C20 C21 C22 85.9(5) . . . . ?
C19 C20 C21 C22 -91.7(6) . . . . ?
O4 C21 C22 C23 63.2(6) . . . . ?
C20 C21 C22 C23 -54.6(7) . . . . ?
C29 C21 C22 C23 -177.4(5) . . . . ?
Co2 O5 C23 C24 35.8(5) . . . . ?
Co1 O5 C23 C24 -75.5(5) . . . . ?
Co2 O5 C23 C30 -81.1(4) . . . . ?
Co1 O5 C23 C30 167.6(3) . . . . ?
Co2 O5 C23 C22 161.3(3) . . . . ?
Co1 O5 C23 C22 50.0(5) . . . . ?
C21 C22 C23 O5 -47.9(6) . . . . ?
C21 C22 C23 C24 72.2(7) . . . . ?
C21 C22 C23 C30 -167.2(5) . . . . ?
C28 N4 C24 C25 -4.3(7) . . . . ?
Co2 N4 C24 C25 179.8(4) . . . . ?
C28 N4 C24 C23 177.5(5) . . . . ?
Co2 N4 C24 C23 1.6(5) . . . . ?
O5 C23 C24 N4 -24.1(6) . . . . ?
C30 C23 C24 N4 93.8(5) . . . . ?
C22 C23 C24 N4 -146.2(5) . . . . ?
O5 C23 C24 C25 157.8(5) . . . . ?
C30 C23 C24 C25 -84.3(7) . . . . ?
C22 C23 C24 C25 35.6(8) . . . . ?
N4 C24 C25 C26 5.0(8) . . . . ?
C23 C24 C25 C26 -177.0(5) . . . . ?
C24 C25 C26 C27 -3.2(8) . . . . ?
C25 C26 C27 C28 0.9(8) . . . . ?
C24 N4 C28 C27 1.7(8) . . . . ?
Co2 N4 C28 C27 177.2(4) . . . . ?
C26 C27 C28 N4 0.0(8) . . . . ?
Co2 O6 C31 O7 -179.5(5) . . . . ?
Co2 O6 C31 O3 0.5(4) . . . . ?
Co2 O3 C31 O7 179.5(5) . . . . ?
Co2 O3 C31 O6 -0.5(4) . . . . ?

_refine_diff_density_max         0.584
_refine_diff_density_min         -0.488
_refine_diff_density_rms         0.061

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_shelx_162B1
_database_code_depnum_ccdc_archive 'CCDC 1529488'
_audit_update_record             
;
2017-03-18 deposited with the CCDC.
2017-06-12 downloaded from the CCDC.
;

_vrf_PLAT058_shelx_162B1         
;
PROBLEM: Maximum Transmission Factor Missing ............          ?
RESPONSE: The maximum transmission factor was lost due to a hard drive failure.
Unfortunately, the raw data was not retrievable. The only surviving
information is the absorption corrected HKL.
;
_vrf_PLAT059_shelx_162B1         
;
PROBLEM: Minimum Transmission Factor Missing ............          ?
RESPONSE: The minimum transmission factor was lost due to a hard drive failure.
Unfortunately, the raw data was not retrievable. The only surviving
information is the absorption corrected HKL.
;
_vrf_PLAT183_shelx_162B1         
;
PROBLEM: Missing _cell_measurement_reflns_used value ....     Please Do !
RESPONSE: The number of reflections used to determine the unit cell
was lost due to a hard drive failure. Unfortunately, the raw data was not
retrievable. The only surviving information is the absorption corrected HKL.
;
_vrf_PLAT184_shelx_162B1         
;
PROBLEM: Missing _cell_measurement_theta_min value ......     Please Do !
RESPONSE: The minimum theta value used to determine the unit cell
was lost due to a hard drive failure. Unfortunately, the raw data was not
retrievable. The only surviving information is the absorption corrected HKL.
;

_vrf_PLAT910_shelx_162B1         
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min)
RESPONSE: These data were collected with a fix-position CCD. It is not
possible to increase the distance from the crystal to the detector,
which prevented the collection of additional images to overcome
this alert. However this does not present a substantial issue; there are 8429
independent reflections and a data/parameter ratio of ~11.
;
_vrf_PLAT185_shelx_162B1         
;
PROBLEM: Missing _cell_measurement_theta_max value ......
RESPONSE: The maximum theta value used to determine the unit cell
was lost due to a hard drive failure. Unfortunately, the raw data was not
retrievable. The only surviving information is the absorption corrected HKL.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H34 Cu N4 O4'
_chemical_formula_sum            'C30 H34 Cu N4 O4'
_chemical_formula_weight         578.15

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.3252(3)
_cell_length_b                   14.6827(5)
_cell_length_c                   11.7096(8)
_cell_angle_alpha                90
_cell_angle_beta                 105.716(7)
_cell_angle_gamma                90
_cell_volume                     1377.83(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       plate
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_F_000             606
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.835
_shelx_estimated_absorpt_T_min   0.851
_shelx_estimated_absorpt_T_max   0.921
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private Communication'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Mercury275R CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 6.8
_diffrn_reflns_number            21525
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.027
_diffrn_reflns_theta_max         27.479
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3146
_reflns_number_gt                2927
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
; 
Dolomanov, O.V.; Bourhis, L.J.; Gildea, R.J.; Howard, J.A.K.; Puschmann, H., 
OLEX2: A complete structure solution, refinement and analysis program
(2009). J. Appl. Cryst., 42, 339-341. 
;
_computing_publication_material  'SHELXL-2013/2 (Sheldrick, 2014)'
_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.

 The hydrogen atoms were first found in the difference map, then generated
 geometrically and refined as riding atoms with C-H distances = 0.95- 0.99
 Å and Uiso(H) = 1.2 times Ueq(C) for CH and CH2 groups and Uiso(H)
 = 1.5 times Ueq(C) for CH3 groups. The only exception is H2,
 which was found in the difference map and semi-freely refined with a distance
 restraint of 0.85(2) Å.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0330P)²+1.1259P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3146
_refine_ls_number_parameters     184
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0323
_refine_ls_wR_factor_ref         0.0805
_refine_ls_wR_factor_gt          0.0789
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.098
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.5000 0.5000 0.5000 0.01443(9) Uani 1 2 d S . P . .
O1 O 0.35871(14) 0.59092(8) 0.41243(10) 0.0172(2) Uani 1 1 d . . . . .
O2 O 0.42648(15) 0.75026(8) 0.51013(10) 0.0181(2) Uani 1 1 d D . . . .
H2 H 0.397(3) 0.6951(12) 0.495(2) 0.040(7) Uiso 1 1 d D . . . .
N1 N 0.64013(17) 0.52592(9) 0.39282(12) 0.0147(3) Uani 1 1 d . . . . .
N2 N 0.72714(19) 0.81985(11) 0.35212(14) 0.0252(3) Uani 1 1 d . . . . .
C1 C 0.7925(2) 0.49098(11) 0.40030(14) 0.0170(3) Uani 1 1 d . . . . .
H1 H 0.8373 0.4465 0.4592 0.020 Uiso 1 1 calc R U . . .
C2 C 0.8853(2) 0.51806(12) 0.32481(15) 0.0195(3) Uani 1 1 d . . . . .
H2A H 0.9932 0.4936 0.3321 0.023 Uiso 1 1 calc R U . . .
C3 C 0.8166(2) 0.58228(12) 0.23758(15) 0.0192(3) Uani 1 1 d . . . . .
H3 H 0.8773 0.6019 0.1841 0.023 Uiso 1 1 calc R U . . .
C4 C 0.6595(2) 0.61729(11) 0.22919(14) 0.0169(3) Uani 1 1 d . . . . .
H4 H 0.6105 0.6602 0.1692 0.020 Uiso 1 1 calc R U . . .
C5 C 0.57443(19) 0.58858(11) 0.31004(13) 0.0138(3) Uani 1 1 d . . . . .
C6 C 0.2782(2) 0.57764(12) 0.19886(15) 0.0207(3) Uani 1 1 d . . . . .
H6A H 0.2888 0.5112 0.2040 0.031 Uiso 1 1 calc R U . . .
H6B H 0.3055 0.5990 0.1270 0.031 Uiso 1 1 calc R U . . .
H6C H 0.1635 0.5951 0.1956 0.031 Uiso 1 1 calc R U . . .
C7 C 0.39893(19) 0.62106(11) 0.30858(13) 0.0147(3) Uani 1 1 d . . . . .
C8 C 0.3816(2) 0.72576(11) 0.29838(14) 0.0159(3) Uani 1 1 d . . . . .
H8A H 0.4226 0.7457 0.2305 0.019 Uiso 1 1 calc R U . . .
H8B H 0.2614 0.7411 0.2792 0.019 Uiso 1 1 calc R U . . .
C9 C 0.4733(2) 0.78158(11) 0.40800(14) 0.0163(3) Uani 1 1 d . . . . .
C10 C 0.4196(2) 0.88133(12) 0.38991(16) 0.0228(4) Uani 1 1 d . . . . .
H10A H 0.2988 0.8858 0.3782 0.034 Uiso 1 1 calc R U . . .
H10B H 0.4484 0.9054 0.3199 0.034 Uiso 1 1 calc R U . . .
H10C H 0.4773 0.9167 0.4600 0.034 Uiso 1 1 calc R U . . .
C11 C 0.8932(2) 0.81674(14) 0.36922(19) 0.0309(4) Uani 1 1 d . . . . .
H11 H 0.9392 0.8482 0.3145 0.037 Uiso 1 1 calc R U . . .
C12 C 1.0011(2) 0.77068(14) 0.4613(2) 0.0313(4) Uani 1 1 d . . . . .
H12 H 1.1178 0.7700 0.4696 0.038 Uiso 1 1 calc R U . . .
C13 C 0.9338(2) 0.72548(13) 0.54130(18) 0.0276(4) Uani 1 1 d . . . . .
H13 H 1.0041 0.6931 0.6060 0.033 Uiso 1 1 calc R U . . .
C14 C 0.7623(2) 0.72789(12) 0.52603(15) 0.0209(3) Uani 1 1 d . . . . .
H14 H 0.7137 0.6975 0.5801 0.025 Uiso 1 1 calc R U . . .
C15 C 0.6633(2) 0.77563(11) 0.43012(15) 0.0182(3) Uani 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.8877(11) 3_666 ?
Cu1 O1 1.8877(11) . ?
Cu1 N1 1.9682(13) 3_666 ?
Cu1 N1 1.9683(13) . ?
O1 C7 1.4168(18) . ?
O2 C9 1.4305(19) . ?
O2 H2 0.851(16) . ?
N1 C5 1.341(2) . ?
N1 C1 1.349(2) . ?
N2 C15 1.342(2) . ?
N2 C11 1.343(2) . ?
C1 C2 1.380(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.394(2) . ?
C2 H2A 0.9500 . ?
C3 C4 1.383(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.393(2) . ?
C4 H4 0.9500 . ?
C5 C7 1.533(2) . ?
C6 C7 1.539(2) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.546(2) . ?
C8 C9 1.540(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.529(2) . ?
C9 C15 1.534(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.379(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.384(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.391(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.389(2) . ?
C14 H14 0.9500 . ?

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 O1 180.0 3_666 . ?
O1 Cu1 N1 84.64(5) 3_666 3_666 ?
O1 Cu1 N1 95.36(5) . 3_666 ?
O1 Cu1 N1 95.36(5) 3_666 . ?
O1 Cu1 N1 84.64(5) . . ?
N1 Cu1 N1 180.0 3_666 . ?
C7 O1 Cu1 115.45(9) . . ?
C9 O2 H2 105.4(17) . . ?
C5 N1 C1 120.01(14) . . ?
C5 N1 Cu1 113.42(11) . . ?
C1 N1 Cu1 126.47(11) . . ?
C15 N2 C11 117.62(17) . . ?
N1 C1 C2 121.88(15) . . ?
N1 C1 H1 119.1 . . ?
C2 C1 H1 119.1 . . ?
C1 C2 C3 118.33(15) . . ?
C1 C2 H2A 120.8 . . ?
C3 C2 H2A 120.8 . . ?
C4 C3 C2 119.71(15) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 118.97(15) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
N1 C5 C4 121.08(14) . . ?
N1 C5 C7 114.99(13) . . ?
C4 C5 C7 123.86(14) . . ?
C7 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C7 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O1 C7 C5 109.84(12) . . ?
O1 C7 C6 109.54(13) . . ?
C5 C7 C6 106.59(13) . . ?
O1 C7 C8 109.76(12) . . ?
C5 C7 C8 112.28(13) . . ?
C6 C7 C8 108.74(13) . . ?
C9 C8 C7 116.75(13) . . ?
C9 C8 H8A 108.1 . . ?
C7 C8 H8A 108.1 . . ?
C9 C8 H8B 108.1 . . ?
C7 C8 H8B 108.1 . . ?
H8A C8 H8B 107.3 . . ?
O2 C9 C10 106.74(13) . . ?
O2 C9 C15 110.03(13) . . ?
C10 C9 C15 109.10(14) . . ?
O2 C9 C8 109.87(13) . . ?
C10 C9 C8 109.51(13) . . ?
C15 C9 C8 111.48(13) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C11 C12 124.02(19) . . ?
N2 C11 H11 118.0 . . ?
C12 C11 H11 118.0 . . ?
C11 C12 C13 117.81(18) . . ?
C11 C12 H12 121.1 . . ?
C13 C12 H12 121.1 . . ?
C12 C13 C14 119.39(18) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
C15 C14 C13 118.71(17) . . ?
C15 C14 H14 120.6 . . ?
C13 C14 H14 120.6 . . ?
N2 C15 C14 122.44(16) . . ?
N2 C15 C9 115.96(15) . . ?
C14 C15 C9 121.59(15) . . ?

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
N1 Cu1 O1 C7 -170.34(11) 3_666 . . . ?
N1 Cu1 O1 C7 9.66(11) . . . . ?
C5 N1 C1 C2 0.2(2) . . . . ?
Cu1 N1 C1 C2 -175.82(12) . . . . ?
N1 C1 C2 C3 -1.1(3) . . . . ?
C1 C2 C3 C4 0.3(3) . . . . ?
C2 C3 C4 C5 1.2(2) . . . . ?
C1 N1 C5 C4 1.4(2) . . . . ?
Cu1 N1 C5 C4 177.91(12) . . . . ?
C1 N1 C5 C7 178.47(14) . . . . ?
Cu1 N1 C5 C7 -4.98(17) . . . . ?
C3 C4 C5 N1 -2.1(2) . . . . ?
C3 C4 C5 C7 -178.91(15) . . . . ?
Cu1 O1 C7 C5 -14.07(15) . . . . ?
Cu1 O1 C7 C6 102.68(12) . . . . ?
Cu1 O1 C7 C8 -137.99(10) . . . . ?
N1 C5 C7 O1 12.21(19) . . . . ?
C4 C5 C7 O1 -170.77(14) . . . . ?
N1 C5 C7 C6 -106.38(15) . . . . ?
C4 C5 C7 C6 70.64(19) . . . . ?
N1 C5 C7 C8 134.64(14) . . . . ?
C4 C5 C7 C8 -48.3(2) . . . . ?
O1 C7 C8 C9 51.58(18) . . . . ?
C5 C7 C8 C9 -70.91(17) . . . . ?
C6 C7 C8 C9 171.40(13) . . . . ?
C7 C8 C9 O2 -53.77(18) . . . . ?
C7 C8 C9 C10 -170.70(13) . . . . ?
C7 C8 C9 C15 68.47(18) . . . . ?
C15 N2 C11 C12 0.3(3) . . . . ?
N2 C11 C12 C13 -0.4(3) . . . . ?
C11 C12 C13 C14 0.1(3) . . . . ?
C12 C13 C14 C15 0.2(3) . . . . ?
C11 N2 C15 C14 0.1(3) . . . . ?
C11 N2 C15 C9 179.49(15) . . . . ?
C13 C14 C15 N2 -0.4(3) . . . . ?
C13 C14 C15 C9 -179.74(15) . . . . ?
O2 C9 C15 N2 -166.79(14) . . . . ?
C10 C9 C15 N2 -50.01(19) . . . . ?
C8 C9 C15 N2 71.05(18) . . . . ?
O2 C9 C15 C14 12.6(2) . . . . ?
C10 C9 C15 C14 129.39(16) . . . . ?
C8 C9 C15 C14 -109.54(17) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O1 0.851(16) 1.793(18) 2.5982(17) 157(2) .

_refine_diff_density_max         0.825
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.055

####################################################################### 
# 
# 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_mini-16098
_database_code_depnum_ccdc_archive 'CCDC 1529497'
_audit_update_record             
;
2017-01-24 deposited with the CCDC.
2017-06-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H40 N4 Ni2 O6, C2 H3 O2, 2(C H2 Cl2)'
_chemical_formula_sum            'C36 H47 Cl4 N4 Ni2 O8'
_chemical_formula_weight         922.99

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   14.8680(4)
_cell_length_b                   16.1416(4)
_cell_length_c                   16.3814(5)
_cell_angle_alpha                90
_cell_angle_beta                 95.451(3)
_cell_angle_gamma                90
_cell_volume                     3913.65(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    11008
_cell_measurement_theta_min      2.1420
_cell_measurement_theta_max      27.4470

_exptl_crystal_description       Plate
_exptl_crystal_colour            Blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.566
_exptl_crystal_F_000             1916
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.291
_shelx_estimated_absorpt_T_min   0.782
_shelx_estimated_absorpt_T_max   0.882
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.96425
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
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. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Rigaku Mercury275R CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 6.8
_diffrn_reflns_number            34082
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_av_R_equivalents  0.0553
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.498
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4488
_reflns_number_gt                3702
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'CrysAlisPro 1.171.39.9d (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.9d (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.9d (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
; 
Dolomanov, O.V.; Bourhis, L.J.; Gildea, R.J.; Howard, J.A.K.; Puschmann, H., 
OLEX2: A complete structure solution, refinement and analysis program
(2009). J. Appl. Cryst., 42, 339-341.
;
_computing_publication_material  'CIFTAB-2013/2 (Sheldrick, 2014)'
_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 

 The hydrogen atoms were first found in the difference map, then generated 
 geometrically and refined as riding atoms with C-H distances = 0.95- 0.99 
 Å and Uiso(H) = 1.2 times Ueq(C) for CH and CH2 groups and Uiso(H) 
 = 1.5 times Ueq(C) for CH3 groups. The only exception was atom H1, which 
 was found in the difference map and semi-freely refined. The O-H distance 
 was restrained to 0.85(2), as suggested by the difference map. Several low angle 
 reflections were obscured by the beam stop and subsequently omitted.
 
 The acetate counter ion was modeled as disordered across the crystallographic 
 2-fold axis. The special position constraints were suppressed and the site occupancies
 were suppressed.
 
 The dichloromethane molecule was positionally disordered. The two models were
 distinguished with atom label suffixes A and B. The site occupancies of the two models
 were fixed near their converged values of equal occupancies. The C-Cl bond distances
 were anticipated to be chemically identical and restrained to reflect this expectation.
 The two models were also refined with the aid of rigid bond restraints as the thermal displacement
 of the atoms within the solvent behave as an ensemble.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0368P)²+4.8973P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     SHELXT
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4488
_refine_ls_number_parameters     298
_refine_ls_number_restraints     25
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0332
_refine_ls_wR_factor_ref         0.0810
_refine_ls_wR_factor_gt          0.0756
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.5000 0.39945(2) 0.2500 0.01338(9) Uani 1 2 d S T P . .
Ni2 Ni 0.5000 0.58096(2) 0.2500 0.01376(10) Uani 1 2 d S T P . .
O1 O 0.59330(9) 0.31496(9) 0.30112(9) 0.0176(3) Uani 1 1 d D . . . .
H1 H 0.578(2) 0.2652(12) 0.3003(18) 0.050(9) Uiso 1 1 d D . . . .
O2 O 0.57829(9) 0.48959(8) 0.30626(8) 0.0138(3) Uani 1 1 d . . . . .
O3 O 0.54967(10) 0.69590(9) 0.30434(9) 0.0206(3) Uani 1 1 d . . . . .
N1 N 0.57609(11) 0.38092(10) 0.15321(10) 0.0149(3) Uani 1 1 d . . . . .
N2 N 0.60492(11) 0.57723(10) 0.17560(10) 0.0145(3) Uani 1 1 d . . . . .
C1 C 0.55169(13) 0.40128(12) 0.07487(13) 0.0172(4) Uani 1 1 d . . . . .
H1A H 0.4962 0.4297 0.0617 0.021 Uiso 1 1 calc R U . . .
C2 C 0.60478(14) 0.38216(13) 0.01267(13) 0.0205(4) Uani 1 1 d . . . . .
H2 H 0.5870 0.3982 -0.0423 0.025 Uiso 1 1 calc R U . . .
C3 C 0.68445(14) 0.33903(13) 0.03225(13) 0.0211(4) Uani 1 1 d . . . . .
H3 H 0.7217 0.3246 -0.0095 0.025 Uiso 1 1 calc R U . . .
C4 C 0.70962(13) 0.31703(12) 0.11282(13) 0.0185(4) Uani 1 1 d . . . . .
H4 H 0.7637 0.2868 0.1269 0.022 Uiso 1 1 calc R U . . .
C5 C 0.65409(13) 0.34012(12) 0.17283(13) 0.0160(4) Uani 1 1 d . . . . .
C6 C 0.67651(13) 0.32827(12) 0.26483(13) 0.0165(4) Uani 1 1 d . . . . .
C7 C 0.71760(13) 0.40833(12) 0.30350(12) 0.0153(4) Uani 1 1 d . . . . .
H7A H 0.7787 0.4142 0.2849 0.018 Uiso 1 1 calc R U . . .
H7B H 0.7259 0.3994 0.3635 0.018 Uiso 1 1 calc R U . . .
C8 C 0.66939(12) 0.49282(12) 0.28898(12) 0.0141(4) Uani 1 1 d . . . . .
C9 C 0.67563(13) 0.52929(11) 0.20298(12) 0.0141(4) Uani 1 1 d . . . . .
C10 C 0.75002(13) 0.52123(12) 0.15804(12) 0.0165(4) Uani 1 1 d . . . . .
H10 H 0.8001 0.4883 0.1785 0.020 Uiso 1 1 calc R U . . .
C11 C 0.75063(14) 0.56144(12) 0.08347(13) 0.0194(4) Uani 1 1 d . . . . .
H11 H 0.8005 0.5554 0.0517 0.023 Uiso 1 1 calc R U . . .
C12 C 0.67769(14) 0.61062(12) 0.05564(13) 0.0192(4) Uani 1 1 d . . . . .
H12 H 0.6764 0.6388 0.0047 0.023 Uiso 1 1 calc R U . . .
C13 C 0.60697(13) 0.61746(12) 0.10407(12) 0.0164(4) Uani 1 1 d . . . . .
H13 H 0.5575 0.6522 0.0860 0.020 Uiso 1 1 calc R U . . .
C14 C 0.73976(14) 0.25536(13) 0.28537(14) 0.0222(5) Uani 1 1 d . . . . .
H14A H 0.7489 0.2484 0.3450 0.033 Uiso 1 1 calc R U . . .
H14B H 0.7980 0.2660 0.2639 0.033 Uiso 1 1 calc R U . . .
H14C H 0.7130 0.2048 0.2604 0.033 Uiso 1 1 calc R U . . .
C15 C 0.72093(13) 0.55476(13) 0.34829(13) 0.0184(4) Uani 1 1 d . . . . .
H15A H 0.6927 0.6095 0.3418 0.028 Uiso 1 1 calc R U . . .
H15B H 0.7840 0.5583 0.3358 0.028 Uiso 1 1 calc R U . . .
H15C H 0.7188 0.5357 0.4049 0.028 Uiso 1 1 calc R U . . .
C16 C 0.5000 0.73541(18) 0.2500 0.0185(6) Uani 1 2 d S T P . .
C17 C 0.5000 0.82727(19) 0.2500 0.0292(7) Uani 1 2 d S T P . .
H17A H 0.4837 0.8475 0.3030 0.044 Uiso 1 1 calc R U . A -1
H17B H 0.4560 0.8475 0.2062 0.044 Uiso 1 1 calc R U . A -1
H17C H 0.5603 0.8475 0.2407 0.044 Uiso 1 1 calc R U . A -1
Cl1A Cl 0.5952(3) 0.1704(3) 0.5344(2) 0.0526(10) Uani 0.5 1 d D U P B 2
Cl2A Cl 0.4146(4) 0.1047(5) 0.5042(5) 0.0611(16) Uani 0.5 1 d D U P B 2
C1A C 0.4988(4) 0.1617(4) 0.4652(4) 0.0461(14) Uani 0.5 1 d D U P B 2
H1AA H 0.4756 0.2178 0.4508 0.055 Uiso 0.5 1 calc R U P B 2
H1AB H 0.5154 0.1350 0.4144 0.055 Uiso 0.5 1 calc R U P B 2
Cl1B Cl 0.5971(3) 0.1521(3) 0.5599(2) 0.0403(7) Uani 0.5 1 d D U P C 1
Cl2B Cl 0.4142(4) 0.0914(4) 0.5168(4) 0.0537(13) Uani 0.5 1 d D U P C 1
C1B C 0.4887(3) 0.1756(3) 0.5161(4) 0.0311(11) Uani 0.5 1 d D U P C 1
H1BA H 0.4922 0.1938 0.4587 0.037 Uiso 0.5 1 calc R U P C 1
H1BB H 0.4644 0.2223 0.5464 0.037 Uiso 0.5 1 calc R U P C 1
O4 O 0.5452(3) 0.1692(2) 0.3313(3) 0.0306(9) Uani 0.5 1 d . . P D -1
O5 O 0.4540(3) 0.1582(2) 0.2158(3) 0.0310(9) Uani 0.5 1 d . . P D -1
C18 C 0.4973(4) 0.1288(3) 0.2767(3) 0.0259(12) Uani 0.5 1 d . . P D -1
C19 C 0.4944(4) 0.0359(3) 0.2890(4) 0.0414(14) Uani 0.5 1 d . . P D -1
H19A H 0.5315 0.0210 0.3395 0.062 Uiso 0.5 1 calc R U P D -1
H19B H 0.4319 0.0183 0.2931 0.062 Uiso 0.5 1 calc R U P D -1
H19C H 0.5180 0.0081 0.2423 0.062 Uiso 0.5 1 calc R U P D -1


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 O2 2.0291(13) . ?
Ni1 O2 2.0292(13) 2_655 ?
Ni1 N1 2.0552(16) 2_655 ?
Ni1 N1 2.0553(16) . ?
Ni1 O1 2.0651(14) . ?
Ni1 O1 2.0651(14) 2_655 ?
Ni1 Ni2 2.9299(5) . ?
Ni2 O2 2.0434(13) 2_655 ?
Ni2 O2 2.0434(13) . ?
Ni2 N2 2.0698(16) . ?
Ni2 N2 2.0698(16) 2_655 ?
Ni2 O3 2.1575(14) 2_655 ?
Ni2 O3 2.1576(15) . ?
Ni2 C16 2.493(3) . ?
O1 C6 1.439(2) . ?
O1 H1 0.833(17) . ?
O2 C8 1.411(2) . ?
O3 C16 1.273(2) . ?
N1 C1 1.341(3) . ?
N1 C5 1.346(2) . ?
N2 C13 1.343(3) . ?
N2 C9 1.347(2) . ?
C1 C2 1.382(3) . ?
C1 H1A 0.9500 . ?
C2 C3 1.385(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.384(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.393(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.524(3) . ?
C6 C14 1.524(3) . ?
C6 C7 1.540(3) . ?
C7 C8 1.549(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.538(3) . ?
C8 C15 1.546(3) . ?
C9 C10 1.392(3) . ?
C10 C11 1.384(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.386(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.380(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 O3 1.273(2) 2_655 ?
C16 C17 1.483(4) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
Cl1A C1A 1.747(7) . ?
Cl2A C1A 1.723(8) . ?
C1A H1AA 0.9900 . ?
C1A H1AB 0.9900 . ?
Cl1B C1B 1.743(6) . ?
Cl2B C1B 1.754(7) . ?
C1B H1BA 0.9900 . ?
C1B H1BB 0.9900 . ?
O4 C18 1.269(7) . ?
O5 C18 1.230(7) . ?
C18 C19 1.516(6) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Ni1 O2 88.37(7) . 2_655 ?
O2 Ni1 N1 95.05(6) . 2_655 ?
O2 Ni1 N1 96.93(6) 2_655 2_655 ?
O2 Ni1 N1 96.93(6) . . ?
O2 Ni1 N1 95.05(6) 2_655 . ?
N1 Ni1 N1 163.26(9) 2_655 . ?
O2 Ni1 O1 87.43(6) . . ?
O2 Ni1 O1 172.72(5) 2_655 . ?
N1 Ni1 O1 89.36(6) 2_655 . ?
N1 Ni1 O1 79.57(6) . . ?
O2 Ni1 O1 172.72(5) . 2_655 ?
O2 Ni1 O1 87.43(6) 2_655 2_655 ?
N1 Ni1 O1 79.57(6) 2_655 2_655 ?
N1 Ni1 O1 89.36(6) . 2_655 ?
O1 Ni1 O1 97.34(8) . 2_655 ?
O2 Ni1 Ni2 44.19(4) . . ?
O2 Ni1 Ni2 44.19(4) 2_655 . ?
N1 Ni1 Ni2 98.37(5) 2_655 . ?
N1 Ni1 Ni2 98.37(5) . . ?
O1 Ni1 Ni2 131.33(4) . . ?
O1 Ni1 Ni2 131.33(4) 2_655 . ?
O2 Ni2 O2 87.60(7) 2_655 . ?
O2 Ni2 N2 98.19(6) 2_655 . ?
O2 Ni2 N2 79.38(6) . . ?
O2 Ni2 N2 79.38(6) 2_655 2_655 ?
O2 Ni2 N2 98.18(6) . 2_655 ?
N2 Ni2 N2 176.67(9) . 2_655 ?
O2 Ni2 O3 106.06(5) 2_655 2_655 ?
O2 Ni2 O3 164.73(5) . 2_655 ?
N2 Ni2 O3 91.70(6) . 2_655 ?
N2 Ni2 O3 91.16(6) 2_655 2_655 ?
O2 Ni2 O3 164.73(5) 2_655 . ?
O2 Ni2 O3 106.06(5) . . ?
N2 Ni2 O3 91.16(6) . . ?
N2 Ni2 O3 91.70(6) 2_655 . ?
O3 Ni2 O3 61.39(8) 2_655 . ?
O2 Ni2 C16 136.20(4) 2_655 . ?
O2 Ni2 C16 136.20(4) . . ?
N2 Ni2 C16 91.67(4) . . ?
N2 Ni2 C16 91.67(4) 2_655 . ?
O3 Ni2 C16 30.69(4) 2_655 . ?
O3 Ni2 C16 30.69(4) . . ?
O2 Ni2 Ni1 43.80(4) 2_655 . ?
O2 Ni2 Ni1 43.80(4) . . ?
N2 Ni2 Ni1 88.33(4) . . ?
N2 Ni2 Ni1 88.33(4) 2_655 . ?
O3 Ni2 Ni1 149.31(4) 2_655 . ?
O3 Ni2 Ni1 149.31(4) . . ?
C16 Ni2 Ni1 180.0 . . ?
C6 O1 Ni1 107.74(11) . . ?
C6 O1 H1 112(2) . . ?
Ni1 O1 H1 118(2) . . ?
C8 O2 Ni1 117.11(11) . . ?
C8 O2 Ni2 113.55(11) . . ?
Ni1 O2 Ni2 92.01(5) . . ?
C16 O3 Ni2 89.38(14) . . ?
C1 N1 C5 119.82(17) . . ?
C1 N1 Ni1 125.72(13) . . ?
C5 N1 Ni1 114.33(13) . . ?
C13 N2 C9 119.12(17) . . ?
C13 N2 Ni2 125.50(13) . . ?
C9 N2 Ni2 115.38(13) . . ?
N1 C1 C2 121.96(19) . . ?
N1 C1 H1A 119.0 . . ?
C2 C1 H1A 119.0 . . ?
C1 C2 C3 118.5(2) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C4 C3 C2 119.85(19) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 118.67(19) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
N1 C5 C4 121.15(19) . . ?
N1 C5 C6 113.58(16) . . ?
C4 C5 C6 125.13(18) . . ?
O1 C6 C14 109.29(16) . . ?
O1 C6 C5 108.15(16) . . ?
C14 C6 C5 112.80(17) . . ?
O1 C6 C7 106.17(15) . . ?
C14 C6 C7 110.17(17) . . ?
C5 C6 C7 110.02(16) . . ?
C6 C7 C8 121.08(16) . . ?
C6 C7 H7A 107.1 . . ?
C8 C7 H7A 107.1 . . ?
C6 C7 H7B 107.1 . . ?
C8 C7 H7B 107.1 . . ?
H7A C7 H7B 106.8 . . ?
O2 C8 C9 109.91(15) . . ?
O2 C8 C15 109.02(15) . . ?
C9 C8 C15 105.00(15) . . ?
O2 C8 C7 112.08(15) . . ?
C9 C8 C7 114.23(15) . . ?
C15 C8 C7 106.18(15) . . ?
N2 C9 C10 120.78(18) . . ?
N2 C9 C8 114.31(16) . . ?
C10 C9 C8 124.68(17) . . ?
C11 C10 C9 119.68(19) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C10 C11 C12 119.24(19) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
C13 C12 C11 118.15(19) . . ?
C13 C12 H12 120.9 . . ?
C11 C12 H12 120.9 . . ?
N2 C13 C12 122.99(19) . . ?
N2 C13 H13 118.5 . . ?
C12 C13 H13 118.5 . . ?
C6 C14 H14A 109.5 . . ?
C6 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C6 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C8 C15 H15A 109.5 . . ?
C8 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C8 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O3 C16 O3 119.9(3) 2_655 . ?
O3 C16 C17 120.07(13) 2_655 . ?
O3 C16 C17 120.07(13) . . ?
O3 C16 Ni2 59.93(13) 2_655 . ?
O3 C16 Ni2 59.93(13) . . ?
C17 C16 Ni2 180.0 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
Cl2A C1A Cl1A 112.5(5) . . ?
Cl2A C1A H1AA 109.1 . . ?
Cl1A C1A H1AA 109.1 . . ?
Cl2A C1A H1AB 109.1 . . ?
Cl1A C1A H1AB 109.1 . . ?
H1AA C1A H1AB 107.8 . . ?
Cl1B C1B Cl2B 112.8(4) . . ?
Cl1B C1B H1BA 109.0 . . ?
Cl2B C1B H1BA 109.0 . . ?
Cl1B C1B H1BB 109.0 . . ?
Cl2B C1B H1BB 109.0 . . ?
H1BA C1B H1BB 107.8 . . ?
O5 C18 O4 126.1(5) . . ?
O5 C18 C19 118.0(5) . . ?
O4 C18 C19 115.8(4) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
C5 N1 C1 C2 -0.5(3) . . . . ?
Ni1 N1 C1 C2 -176.09(15) . . . . ?
N1 C1 C2 C3 1.5(3) . . . . ?
C1 C2 C3 C4 -0.8(3) . . . . ?
C2 C3 C4 C5 -0.9(3) . . . . ?
C1 N1 C5 C4 -1.2(3) . . . . ?
Ni1 N1 C5 C4 174.85(14) . . . . ?
C1 N1 C5 C6 174.82(16) . . . . ?
Ni1 N1 C5 C6 -9.1(2) . . . . ?
C3 C4 C5 N1 1.9(3) . . . . ?
C3 C4 C5 C6 -173.68(18) . . . . ?
Ni1 O1 C6 C14 -166.87(13) . . . . ?
Ni1 O1 C6 C5 -43.73(16) . . . . ?
Ni1 O1 C6 C7 74.32(15) . . . . ?
N1 C5 C6 O1 35.6(2) . . . . ?
C4 C5 C6 O1 -148.53(18) . . . . ?
N1 C5 C6 C14 156.58(17) . . . . ?
C4 C5 C6 C14 -27.5(3) . . . . ?
N1 C5 C6 C7 -80.0(2) . . . . ?
C4 C5 C6 C7 95.9(2) . . . . ?
O1 C6 C7 C8 -64.6(2) . . . . ?
C14 C6 C7 C8 177.15(17) . . . . ?
C5 C6 C7 C8 52.2(2) . . . . ?
Ni1 O2 C8 C9 75.13(16) . . . . ?
Ni2 O2 C8 C9 -30.31(17) . . . . ?
Ni1 O2 C8 C15 -170.29(12) . . . . ?
Ni2 O2 C8 C15 84.27(16) . . . . ?
Ni1 O2 C8 C7 -53.04(18) . . . . ?
Ni2 O2 C8 C7 -158.48(12) . . . . ?
C6 C7 C8 O2 51.5(2) . . . . ?
C6 C7 C8 C9 -74.3(2) . . . . ?
C6 C7 C8 C15 170.49(17) . . . . ?
C13 N2 C9 C10 0.0(3) . . . . ?
Ni2 N2 C9 C10 179.49(14) . . . . ?
C13 N2 C9 C8 174.72(16) . . . . ?
Ni2 N2 C9 C8 -5.8(2) . . . . ?
O2 C8 C9 N2 23.5(2) . . . . ?
C15 C8 C9 N2 -93.62(18) . . . . ?
C7 C8 C9 N2 150.47(16) . . . . ?
O2 C8 C9 C10 -161.99(17) . . . . ?
C15 C8 C9 C10 80.9(2) . . . . ?
C7 C8 C9 C10 -35.0(3) . . . . ?
N2 C9 C10 C11 -1.4(3) . . . . ?
C8 C9 C10 C11 -175.61(18) . . . . ?
C9 C10 C11 C12 1.4(3) . . . . ?
C10 C11 C12 C13 0.1(3) . . . . ?
C9 N2 C13 C12 1.6(3) . . . . ?
Ni2 N2 C13 C12 -177.90(15) . . . . ?
C11 C12 C13 N2 -1.6(3) . . . . ?
Ni2 O3 C16 O3 0.000(0) . . . 2_655 ?
Ni2 O3 C16 C17 180.000(0) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O4 0.833(17) 1.717(19) 2.522(4) 162(3) .
O1 H1 O5 0.833(17) 1.806(18) 2.634(4) 173(3) 2_655

_refine_diff_density_max         0.351
_refine_diff_density_min         -0.492
_refine_diff_density_rms         0.081

####################################################################### 
# 
# 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_shelx_163B1
_database_code_depnum_ccdc_archive 'CCDC 1529496'
_audit_update_record             
;
2017-03-18 deposited with the CCDC.
2017-06-12 downloaded from the CCDC.
;

_vrf_PLAT058_shelx_163B1         
;
PROBLEM: Maximum Transmission Factor Missing ............          ?      
RESPONSE: The maximum transmission factor was lost due to a hard drive failure.
Unfortunately, the raw data was not retrievable. The only surviving 
information is the absorption corrected HKL.
;
_vrf_PLAT059_shelx_163B1         
;
PROBLEM: Minimum Transmission Factor Missing ............          ?      
RESPONSE: The minimum transmission factor was lost due to a hard drive failure.
Unfortunately, the raw data was not retrievable. The only surviving 
information is the absorption corrected HKL.
;
_vrf_PLAT183_shelx_163B1         
;
PROBLEM: Missing _cell_measurement_reflns_used value ....     Please Do ! 
RESPONSE: The number of reflections used to determine the unit cell 
was lost due to a hard drive failure. Unfortunately, the raw data was not 
retrievable. The only surviving information is the absorption corrected HKL.
;
_vrf_PLAT184_shelx_163B1         
;
PROBLEM: Missing _cell_measurement_theta_min value ......     Please Do ! 
RESPONSE: The minimum theta value used to determine the unit cell 
was lost due to a hard drive failure. Unfortunately, the raw data was not 
retrievable. The only surviving information is the absorption corrected HKL.
;

_vrf_PLAT185_shelx_163B1         
; 

PROBLEM: Missing _cell_measurement_theta_max value ......
RESPONSE: The maximum theta value used to determine the unit cell 
was lost due to a hard drive failure. Unfortunately, the raw data was not 
retrievable. The only surviving information is the absorption corrected HKL.

;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H34 N4 Ni O4'
_chemical_formula_sum            'C30 H34 N4 Ni O4'
_chemical_formula_weight         573.32

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'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.3214(5)
_cell_length_b                   14.6642(9)
_cell_length_c                   11.6946(8)
_cell_angle_alpha                90
_cell_angle_beta                 105.640(7)
_cell_angle_gamma                90
_cell_volume                     1374.22(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Plate
_exptl_crystal_colour            Brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_F_000             604
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.749
_shelx_estimated_absorpt_T_min   0.865
_shelx_estimated_absorpt_T_max   0.929
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Mercury275R CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 6.8
_diffrn_reflns_number            20526
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.031
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3136
_reflns_number_gt                2892
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
; 
Dolomanov, O.V.; Bourhis, L.J.; Gildea, R.J.; Howard, J.A.K.; Puschmann, H., 
OLEX2: A complete structure solution, refinement and analysis program
(2009). J. Appl. Cryst., 42, 339-341.
;
_computing_publication_material  'CIFTAB-2013/2 (Sheldrick, 2014)'
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.

 The hydrogen atoms were first found in the difference map, then generated
 geometrically and refined as riding atoms with C-H distances = 0.95- 0.99
 Å and Uiso(H) = 1.2 times Ueq(C) for CH and CH2 groups and Uiso(H)
 = 1.5 times Ueq(C) for CH3 groups. The only exception is H2,
 which was found in the difference map and freely refined.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0225P)²+0.9783P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     SHELXT
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3136
_refine_ls_number_parameters     184
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0339
_refine_ls_wR_factor_ref         0.0710
_refine_ls_wR_factor_gt          0.0691
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_restrained_S_all      1.135
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.5000 0.5000 0.5000 0.01190(8) Uani 1 2 d S . P . .
O1 O 0.35939(14) 0.40930(8) 0.41389(10) 0.0168(2) Uani 1 1 d . . . . .
O2 O 0.42663(14) 0.24943(8) 0.51143(10) 0.0176(2) Uani 1 1 d . . . . .
H2 H 0.400(3) 0.3067(16) 0.497(2) 0.037(6) Uiso 1 1 d . . . . .
N1 N 0.63893(16) 0.47441(9) 0.39409(11) 0.0151(3) Uani 1 1 d . . . . .
N2 N 0.72688(18) 0.17995(10) 0.35228(14) 0.0236(3) Uani 1 1 d . . . . .
C1 C 0.79123(19) 0.50975(11) 0.40173(14) 0.0171(3) Uani 1 1 d . . . . .
H1 H 0.8356 0.5544 0.4607 0.020 Uiso 1 1 calc R U . . .
C2 C 0.8843(2) 0.48269(11) 0.32601(15) 0.0188(3) Uani 1 1 d . . . . .
H2A H 0.9922 0.5074 0.3335 0.023 Uiso 1 1 calc R U . . .
C3 C 0.8165(2) 0.41857(11) 0.23866(14) 0.0186(3) Uani 1 1 d . . . . .
H3 H 0.8777 0.3992 0.1851 0.022 Uiso 1 1 calc R U . . .
C4 C 0.6599(2) 0.38313(11) 0.23010(14) 0.0164(3) Uani 1 1 d . . . . .
H4 H 0.6116 0.3400 0.1700 0.020 Uiso 1 1 calc R U . . .
C5 C 0.57380(19) 0.41155(10) 0.31089(13) 0.0141(3) Uani 1 1 d . . . . .
C6 C 0.2779(2) 0.42264(12) 0.19979(15) 0.0204(3) Uani 1 1 d . . . . .
H6A H 0.1632 0.4052 0.1969 0.031 Uiso 1 1 calc R U . . .
H6B H 0.3049 0.4013 0.1277 0.031 Uiso 1 1 calc R U . . .
H6C H 0.2886 0.4892 0.2050 0.031 Uiso 1 1 calc R U . . .
C7 C 0.39908(19) 0.37905(10) 0.30945(13) 0.0149(3) Uani 1 1 d . . . . .
C8 C 0.38114(19) 0.27417(11) 0.29915(13) 0.0154(3) Uani 1 1 d . . . . .
H8A H 0.2609 0.2590 0.2803 0.019 Uiso 1 1 calc R U . . .
H8B H 0.4217 0.2541 0.2310 0.019 Uiso 1 1 calc R U . . .
C9 C 0.47324(19) 0.21812(11) 0.40887(14) 0.0160(3) Uani 1 1 d . . . . .
C10 C 0.4199(2) 0.11831(11) 0.39083(15) 0.0214(3) Uani 1 1 d . . . . .
H10A H 0.4773 0.0830 0.4611 0.032 Uiso 1 1 calc R U . . .
H10B H 0.4493 0.0942 0.3209 0.032 Uiso 1 1 calc R U . . .
H10C H 0.2990 0.1138 0.3789 0.032 Uiso 1 1 calc R U . . .
C11 C 0.8928(2) 0.18285(13) 0.36922(18) 0.0278(4) Uani 1 1 d . . . . .
H11 H 0.9387 0.1513 0.3144 0.033 Uiso 1 1 calc R U . . .
C12 C 1.0009(2) 0.22895(13) 0.46152(18) 0.0280(4) Uani 1 1 d . . . . .
H12 H 1.1177 0.2294 0.4698 0.034 Uiso 1 1 calc R U . . .
C13 C 0.9337(2) 0.27459(12) 0.54174(17) 0.0252(4) Uani 1 1 d . . . . .
H13 H 1.0040 0.3072 0.6063 0.030 Uiso 1 1 calc R U . . .
C14 C 0.7626(2) 0.27207(11) 0.52671(15) 0.0196(3) Uani 1 1 d . . . . .
H14 H 0.7142 0.3025 0.5810 0.024 Uiso 1 1 calc R U . . .
C15 C 0.6633(2) 0.22427(11) 0.43083(14) 0.0174(3) Uani 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 O1 1.8753(11) 3_666 ?
Ni1 O1 1.8753(11) . ?
Ni1 N1 1.9451(13) . ?
Ni1 N1 1.9452(13) 3_666 ?
O1 C7 1.4195(18) . ?
O2 C9 1.4321(18) . ?
O2 H2 0.87(2) . ?
N1 C5 1.344(2) . ?
N1 C1 1.350(2) . ?
N2 C11 1.341(2) . ?
N2 C15 1.345(2) . ?
C1 C2 1.382(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.391(2) . ?
C2 H2A 0.9500 . ?
C3 C4 1.381(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.395(2) . ?
C4 H4 0.9500 . ?
C5 C7 1.526(2) . ?
C6 C7 1.540(2) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.547(2) . ?
C8 C9 1.542(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.527(2) . ?
C9 C15 1.535(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.381(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.387(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.387(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.390(2) . ?
C14 H14 0.9500 . ?

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 Ni1 O1 180.0 3_666 . ?
O1 Ni1 N1 94.98(5) 3_666 . ?
O1 Ni1 N1 85.02(5) . . ?
O1 Ni1 N1 85.02(5) 3_666 3_666 ?
O1 Ni1 N1 94.98(5) . 3_666 ?
N1 Ni1 N1 180.0 . 3_666 ?
C7 O1 Ni1 115.30(9) . . ?
C9 O2 H2 105.0(15) . . ?
C5 N1 C1 119.97(14) . . ?
C5 N1 Ni1 113.60(10) . . ?
C1 N1 Ni1 126.33(11) . . ?
C11 N2 C15 117.56(16) . . ?
N1 C1 C2 121.71(15) . . ?
N1 C1 H1 119.1 . . ?
C2 C1 H1 119.1 . . ?
C1 C2 C3 118.58(15) . . ?
C1 C2 H2A 120.7 . . ?
C3 C2 H2A 120.7 . . ?
C4 C3 C2 119.68(15) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 119.05(15) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
N1 C5 C4 120.99(14) . . ?
N1 C5 C7 114.79(13) . . ?
C4 C5 C7 124.15(14) . . ?
C7 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C7 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O1 C7 C5 109.57(12) . . ?
O1 C7 C6 109.57(13) . . ?
C5 C7 C6 106.70(12) . . ?
O1 C7 C8 109.74(12) . . ?
C5 C7 C8 112.52(13) . . ?
C6 C7 C8 108.66(13) . . ?
C9 C8 C7 116.69(13) . . ?
C9 C8 H8A 108.1 . . ?
C7 C8 H8A 108.1 . . ?
C9 C8 H8B 108.1 . . ?
C7 C8 H8B 108.1 . . ?
H8A C8 H8B 107.3 . . ?
O2 C9 C10 106.79(13) . . ?
O2 C9 C15 109.91(12) . . ?
C10 C9 C15 109.09(13) . . ?
O2 C9 C8 109.87(12) . . ?
C10 C9 C8 109.58(13) . . ?
C15 C9 C8 111.49(13) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C11 C12 123.97(17) . . ?
N2 C11 H11 118.0 . . ?
C12 C11 H11 118.0 . . ?
C11 C12 C13 117.90(17) . . ?
C11 C12 H12 121.1 . . ?
C13 C12 H12 121.1 . . ?
C12 C13 C14 119.26(17) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
C13 C14 C15 118.85(16) . . ?
C13 C14 H14 120.6 . . ?
C15 C14 H14 120.6 . . ?
N2 C15 C14 122.46(15) . . ?
N2 C15 C9 115.77(14) . . ?
C14 C15 C9 121.76(14) . . ?

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
N1 Ni1 O1 C7 -9.94(10) . . . . ?
N1 Ni1 O1 C7 170.06(10) 3_666 . . . ?
C5 N1 C1 C2 -0.3(2) . . . . ?
Ni1 N1 C1 C2 175.93(12) . . . . ?
N1 C1 C2 C3 1.2(2) . . . . ?
C1 C2 C3 C4 -0.5(2) . . . . ?
C2 C3 C4 C5 -1.0(2) . . . . ?
C1 N1 C5 C4 -1.2(2) . . . . ?
Ni1 N1 C5 C4 -177.95(12) . . . . ?
C1 N1 C5 C7 -178.38(13) . . . . ?
Ni1 N1 C5 C7 4.90(16) . . . . ?
C3 C4 C5 N1 1.9(2) . . . . ?
C3 C4 C5 C7 178.76(14) . . . . ?
Ni1 O1 C7 C5 14.33(15) . . . . ?
Ni1 O1 C7 C6 -102.42(12) . . . . ?
Ni1 O1 C7 C8 138.35(10) . . . . ?
N1 C5 C7 O1 -12.28(18) . . . . ?
C4 C5 C7 O1 170.68(14) . . . . ?
N1 C5 C7 C6 106.25(15) . . . . ?
C4 C5 C7 C6 -70.79(18) . . . . ?
N1 C5 C7 C8 -134.66(14) . . . . ?
C4 C5 C7 C8 48.3(2) . . . . ?
O1 C7 C8 C9 -51.60(17) . . . . ?
C5 C7 C8 C9 70.68(17) . . . . ?
C6 C7 C8 C9 -171.39(13) . . . . ?
C7 C8 C9 O2 53.95(17) . . . . ?
C7 C8 C9 C10 170.98(13) . . . . ?
C7 C8 C9 C15 -68.15(17) . . . . ?
C15 N2 C11 C12 -0.5(3) . . . . ?
N2 C11 C12 C13 0.3(3) . . . . ?
C11 C12 C13 C14 0.2(3) . . . . ?
C12 C13 C14 C15 -0.5(2) . . . . ?
C11 N2 C15 C14 0.2(2) . . . . ?
C11 N2 C15 C9 -179.26(14) . . . . ?
C13 C14 C15 N2 0.3(2) . . . . ?
C13 C14 C15 C9 179.71(15) . . . . ?
O2 C9 C15 N2 166.81(13) . . . . ?
C10 C9 C15 N2 50.04(18) . . . . ?
C8 C9 C15 N2 -71.12(18) . . . . ?
O2 C9 C15 C14 -12.6(2) . . . . ?
C10 C9 C15 C14 -129.38(16) . . . . ?
C8 C9 C15 C14 109.46(16) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O1 0.87(2) 1.77(2) 2.6011(16) 157(2) .

_refine_diff_density_max         0.785
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.050

####################################################################### 
# 
# 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_007-15178-mnt3-largebox_sq
_database_code_depnum_ccdc_archive 'CCDC 1529494'
_audit_update_record             
;
2017-01-24 deposited with the CCDC.
2017-06-12 downloaded from the CCDC.
;

_vrf_PLAT869_007-15178-mnt3-largebox_sq 
;
PROBLEM: ALERTS Related to the use of SQUEEZE Suppressed  
RESPONSE: See the "_refine_special_details" and "_platon_squeeze_details"
of the .cif.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C45 H46 Cl4 Mn3 N6 O6'
_chemical_formula_weight         1073.50

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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn -0.5299 2.8052 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'

_cell_length_a                   33.988(2)
_cell_length_b                   22.4348(4)
_cell_length_c                   25.8057(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     19677.2(12)
_cell_formula_units_Z            16
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    148780
_cell_measurement_theta_min      2.6
_cell_measurement_theta_max      66.6

_exptl_crystal_description       Plate
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_F_000             8784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    8.595
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.527
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private Communication'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Rotating Anode'
_diffrn_measurement_device_type  'Rigaku Saturn 944+ CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 22.2
_diffrn_reflns_number            176757
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_av_R_equivalents  0.0650
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.600
_diffrn_reflns_theta_max         66.594
_diffrn_reflns_theta_full        66.594
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8699
_reflns_number_gt                8424
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.952
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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. 
;

_computing_data_collection       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
; 
Dolomanov, O.V.; Bourhis, L.J.; Gildea, R.J.; Howard, J.A.K.; Puschmann, H., 
OLEX2: A complete structure solution, refinement and analysis program 
(2009). J. Appl. Cryst., 42, 339-341. 
;
_computing_publication_material  'SHELXL-2013/2 (Sheldrick, 2014)'
_refine_special_details          
; 
 Refined as a 2-component twin. 

 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 

 The hydrogen atoms were first found in the difference map, then generated 
 geometrically and refined as riding atoms with C-H distances = 0.95- 0.99 
 Å and Uiso(H) = 1.2 times Ueq(C) for CH and CH2 groups and Uiso(H) 
 = 1.5 times Ueq(C) for CH3 groups. 

The program SQUEEZE was used to compensate for the contribution of disordered solvents contained in the voids in the crystal lattice from the diffraction intensities (Acta Cryst. 2009, D65, 148-155). This procedure was applied to the data file and the submitted model is based on the solvent removed data. Based on the total electron density found in the voids (860e/ 2400 A3), it is likely that ~20.5 DCM molecules are present in the unit cell. See platon squeeze details in the .cif for more information.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0703P)²+211.1988P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 3883 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.0066(13)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         8699
_refine_ls_number_parameters     582
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0515
_refine_ls_wR_factor_ref         0.1391
_refine_ls_wR_factor_gt          0.1372
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.40288(3) 0.74018(5) 0.53023(5) 0.0209(2) Uani 1 1 d . . . . .
Mn2 Mn 0.49056(3) 0.75035(5) 0.52790(6) 0.0212(2) Uani 1 1 d . . . . .
Mn3 Mn 0.58236(3) 0.75982(6) 0.52687(6) 0.0300(3) Uani 1 1 d . . . . .
Cl1 Cl 0.62916(6) 0.83336(10) 0.49090(8) 0.0398(5) Uani 1 1 d . . . . .
Cl2 Cl 0.63365(13) 0.6934(2) 0.56398(14) 0.0962(12) Uani 1 1 d . . . . .
O1 O 0.37115(14) 0.6743(2) 0.51464(18) 0.0237(11) Uani 1 1 d . . . . .
O2 O 0.44988(14) 0.6912(2) 0.51764(17) 0.0210(10) Uani 1 1 d . . . . .
O3 O 0.53179(14) 0.6942(2) 0.5282(2) 0.0248(10) Uani 1 1 d . . . . .
O4 O 0.36499(15) 0.7974(2) 0.54715(19) 0.0257(11) Uani 1 1 d . . . . .
O5 O 0.44531(15) 0.7994(2) 0.54003(18) 0.0232(11) Uani 1 1 d . . . . .
O6 O 0.52588(15) 0.8151(2) 0.5260(2) 0.0263(11) Uani 1 1 d . . . . .
N1 N 0.39250(18) 0.7510(3) 0.4433(2) 0.0217(13) Uani 1 1 d . . . . .
N2 N 0.48545(18) 0.7450(3) 0.4406(3) 0.0215(13) Uani 1 1 d . . . . .
N3 N 0.57891(18) 0.7100(3) 0.4483(3) 0.0275(14) Uani 1 1 d . . . . .
N4 N 0.39528(17) 0.7270(3) 0.6181(2) 0.0211(12) Uani 1 1 d . . . . .
N5 N 0.48672(17) 0.7547(3) 0.6156(3) 0.0214(13) Uani 1 1 d . . . . .
N6 N 0.5741(2) 0.8097(3) 0.6047(2) 0.0326(16) Uani 1 1 d . . . . .
C1 C 0.3967(2) 0.7976(3) 0.4120(3) 0.0256(16) Uani 1 1 d . . . . .
H1 H 0.4084 0.8321 0.4248 0.031 Uiso 1 1 calc R U . . .
C2 C 0.3840(2) 0.7964(3) 0.3606(3) 0.0289(16) Uani 1 1 d . . . . .
H2 H 0.3860 0.8299 0.3396 0.035 Uiso 1 1 calc R U . . .
C3 C 0.3684(3) 0.7441(4) 0.3420(3) 0.0346(19) Uani 1 1 d . . . . .
H3 H 0.3593 0.7418 0.3081 0.042 Uiso 1 1 calc R U . . .
C4 C 0.3662(3) 0.6940(4) 0.3747(3) 0.0362(19) Uani 1 1 d . . . . .
H4 H 0.3569 0.6579 0.3620 0.043 Uiso 1 1 calc R U . . .
C5 C 0.3780(2) 0.6990(3) 0.4252(3) 0.0239(15) Uani 1 1 d . . . . .
C6 C 0.3474(2) 0.6031(3) 0.4537(3) 0.0306(17) Uani 1 1 d . . . . .
H6A H 0.3481 0.5726 0.4798 0.046 Uiso 1 1 calc R U . . .
H6B H 0.3521 0.5856 0.4204 0.046 Uiso 1 1 calc R U . . .
H6C H 0.3220 0.6219 0.4538 0.046 Uiso 1 1 calc R U . . .
C7 C 0.3784(2) 0.6486(3) 0.4649(3) 0.0251(15) Uani 1 1 d . . . . .
C8 C 0.4195(2) 0.6169(3) 0.4647(3) 0.0243(15) Uani 1 1 d . . . . .
H8A H 0.4191 0.5866 0.4916 0.029 Uiso 1 1 calc R U . . .
H8B H 0.4223 0.5963 0.4319 0.029 Uiso 1 1 calc R U . . .
C9 C 0.4566(2) 0.6548(3) 0.4728(3) 0.0233(15) Uani 1 1 d . . . . .
C10 C 0.4921(2) 0.6152(3) 0.4857(3) 0.0226(15) Uani 1 1 d . . . . .
H10A H 0.4948 0.5863 0.4579 0.027 Uiso 1 1 calc R U . . .
H10B H 0.4857 0.5930 0.5168 0.027 Uiso 1 1 calc R U . . .
C11 C 0.5332(2) 0.6440(3) 0.4942(3) 0.0266(16) Uani 1 1 d . . . . .
C12 C 0.5590(2) 0.5962(4) 0.5196(3) 0.0347(18) Uani 1 1 d . . . . .
H12A H 0.5848 0.6120 0.5256 0.052 Uiso 1 1 calc R U . . .
H12B H 0.5608 0.5622 0.4971 0.052 Uiso 1 1 calc R U . . .
H12C H 0.5475 0.5843 0.5520 0.052 Uiso 1 1 calc R U . . .
C13 C 0.4994(2) 0.7818(4) 0.4040(3) 0.0259(16) Uani 1 1 d . . . . .
H13 H 0.5132 0.8157 0.4137 0.031 Uiso 1 1 calc R U . . .
C14 C 0.4934(2) 0.7700(4) 0.3521(3) 0.0289(17) Uani 1 1 d . . . . .
H14 H 0.5021 0.7969 0.3271 0.035 Uiso 1 1 calc R U . . .
C15 C 0.4746(2) 0.7184(4) 0.3374(3) 0.0302(17) Uani 1 1 d . . . . .
H15 H 0.4706 0.7100 0.3025 0.036 Uiso 1 1 calc R U . . .
C16 C 0.4616(2) 0.6789(4) 0.3750(3) 0.0292(17) Uani 1 1 d . . . . .
H16 H 0.4497 0.6432 0.3658 0.035 Uiso 1 1 calc R U . . .
C17 C 0.4669(2) 0.6938(3) 0.4268(3) 0.0210(14) Uani 1 1 d . . . . .
C18 C 0.6014(2) 0.7241(4) 0.4081(3) 0.0325(18) Uani 1 1 d . . . . .
H18 H 0.6180 0.7569 0.4110 0.039 Uiso 1 1 calc R U . . .
C19 C 0.6015(3) 0.6923(4) 0.3620(3) 0.038(2) Uani 1 1 d . . . . .
H19 H 0.6178 0.7040 0.3348 0.046 Uiso 1 1 calc R U . . .
C20 C 0.5775(3) 0.6437(4) 0.3569(3) 0.040(2) Uani 1 1 d . . . . .
H20 H 0.5770 0.6215 0.3265 0.048 Uiso 1 1 calc R U . . .
C21 C 0.5537(2) 0.6287(4) 0.3996(3) 0.0336(18) Uani 1 1 d . . . . .
H21 H 0.5370 0.5960 0.3975 0.040 Uiso 1 1 calc R U . . .
C22 C 0.5550(2) 0.6620(4) 0.4444(3) 0.0272(16) Uani 1 1 d . . . . .
C23 C 0.4028(2) 0.6816(3) 0.6504(3) 0.0256(15) Uani 1 1 d . . . . .
H23 H 0.4165 0.6488 0.6378 0.031 Uiso 1 1 calc R U . . .
C24 C 0.3909(3) 0.6815(3) 0.7019(3) 0.0310(17) Uani 1 1 d . . . . .
H24 H 0.3966 0.6495 0.7235 0.037 Uiso 1 1 calc R U . . .
C25 C 0.3704(3) 0.7303(4) 0.7198(3) 0.0354(19) Uani 1 1 d . . . . .
H25 H 0.3615 0.7314 0.7539 0.042 Uiso 1 1 calc R U . . .
C26 C 0.3630(2) 0.7781(3) 0.6866(3) 0.0276(16) Uani 1 1 d . . . . .
H26 H 0.3494 0.8113 0.6985 0.033 Uiso 1 1 calc R U . . .
C27 C 0.3761(2) 0.7756(3) 0.6358(3) 0.0221(14) Uani 1 1 d . . . . .
C28 C 0.3352(2) 0.8645(4) 0.6069(3) 0.0324(18) Uani 1 1 d . . . . .
H28B H 0.3383 0.8826 0.6403 0.049 Uiso 1 1 calc R U . . .
H28A H 0.3119 0.8405 0.6066 0.049 Uiso 1 1 calc R U . . .
H28C H 0.3331 0.8951 0.5809 0.049 Uiso 1 1 calc R U . . .
C29 C 0.3711(2) 0.8252(3) 0.5952(3) 0.0256(15) Uani 1 1 d . . . . .
C30 C 0.4081(2) 0.8659(3) 0.5947(3) 0.0225(15) Uani 1 1 d . . . . .
H30A H 0.4040 0.8964 0.5686 0.027 Uiso 1 1 calc R U . . .
H30B H 0.4094 0.8859 0.6280 0.027 Uiso 1 1 calc R U . . .
C31 C 0.4485(2) 0.8377(3) 0.5845(3) 0.0212(14) Uani 1 1 d . . . . .
C32 C 0.4796(2) 0.8847(3) 0.5696(3) 0.0256(15) Uani 1 1 d . . . . .
H32A H 0.4704 0.9044 0.5385 0.031 Uiso 1 1 calc R U . . .
H32B H 0.4799 0.9145 0.5969 0.031 Uiso 1 1 calc R U . . .
C33 C 0.5226(2) 0.8660(3) 0.5600(3) 0.0269(16) Uani 1 1 d . . . . .
C34 C 0.5423(2) 0.9186(3) 0.5324(4) 0.0359(18) Uani 1 1 d . . . . .
H34A H 0.5680 0.9070 0.5206 0.054 Uiso 1 1 calc R U . . .
H34B H 0.5447 0.9515 0.5560 0.054 Uiso 1 1 calc R U . . .
H34C H 0.5266 0.9304 0.5032 0.054 Uiso 1 1 calc R U . . .
C35 C 0.5042(2) 0.7202(3) 0.6521(3) 0.0237(15) Uani 1 1 d . . . . .
H35 H 0.5204 0.6891 0.6417 0.028 Uiso 1 1 calc R U . . .
C36 C 0.4982(2) 0.7305(4) 0.7044(3) 0.0289(17) Uani 1 1 d . . . . .
H36 H 0.5103 0.7065 0.7292 0.035 Uiso 1 1 calc R U . . .
C37 C 0.4739(2) 0.7775(4) 0.7194(3) 0.0307(17) Uani 1 1 d . . . . .
H37 H 0.4686 0.7841 0.7543 0.037 Uiso 1 1 calc R U . . .
C38 C 0.4576(2) 0.8140(3) 0.6819(3) 0.0265(16) Uani 1 1 d . . . . .
H38 H 0.4424 0.8468 0.6912 0.032 Uiso 1 1 calc R U . . .
C39 C 0.4645(2) 0.8011(3) 0.6301(3) 0.0219(14) Uani 1 1 d . . . . .
C40 C 0.5985(2) 0.7995(4) 0.6455(3) 0.0365(19) Uani 1 1 d . . . . .
H40 H 0.6179 0.7705 0.6424 0.044 Uiso 1 1 calc R U . . .
C41 C 0.5956(3) 0.8305(5) 0.6911(4) 0.047(3) Uani 1 1 d . . . . .
H41 H 0.6113 0.8209 0.7193 0.056 Uiso 1 1 calc R U . . .
C42 C 0.5691(3) 0.8757(6) 0.6940(4) 0.056(3) Uani 1 1 d . . . . .
H42 H 0.5678 0.8984 0.7241 0.067 Uiso 1 1 calc R U . . .
C43 C 0.5438(3) 0.8890(5) 0.6531(4) 0.044(2) Uani 1 1 d . . . . .
H43 H 0.5256 0.9200 0.6553 0.053 Uiso 1 1 calc R U . . .
C44 C 0.5470(2) 0.8533(4) 0.6085(3) 0.0317(18) Uani 1 1 d . . . . .
Cl3 Cl 0.28402(9) 0.68290(13) 0.63846(12) 0.0653(8) Uani 1 1 d . . . . .
Cl4 Cl 0.25809(6) 0.66836(9) 0.53136(11) 0.0438(5) Uani 1 1 d . . . . .
C45 C 0.2956(3) 0.6956(4) 0.5728(5) 0.052(3) Uani 1 1 d . . . . .
H45A H 0.3202 0.6761 0.5645 0.062 Uiso 1 1 calc R U . . .
H45B H 0.2989 0.7381 0.5671 0.062 Uiso 1 1 calc 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
Mn1 O4 1.870(5) . ?
Mn1 O1 1.874(5) . ?
Mn1 O2 1.966(5) . ?
Mn1 O5 1.978(5) . ?
Mn1 N1 2.285(6) . ?
Mn1 N4 2.301(6) . ?
Mn1 Mn2 2.9892(14) . ?
Mn2 O3 1.885(5) . ?
Mn2 O6 1.885(5) . ?
Mn2 O5 1.917(5) . ?
Mn2 O2 1.934(5) . ?
Mn2 N2 2.262(7) . ?
Mn2 N5 2.268(7) . ?
Mn2 Mn3 3.1276(15) . ?
Mn3 O3 2.264(5) . ?
Mn3 O6 2.286(5) . ?
Mn3 N6 2.316(7) . ?
Mn3 N3 2.317(7) . ?
Mn3 Cl1 2.473(2) . ?
Mn3 Cl2 2.486(5) . ?
O1 C7 1.428(8) . ?
O2 C9 1.435(9) . ?
O3 C11 1.430(9) . ?
O4 C29 1.402(9) . ?
O5 C31 1.437(8) . ?
O6 C33 1.443(9) . ?
N1 C1 1.330(10) . ?
N1 C5 1.349(9) . ?
N2 C13 1.340(10) . ?
N2 C17 1.359(10) . ?
N3 C18 1.329(10) . ?
N3 C22 1.353(10) . ?
N4 C23 1.340(9) . ?
N4 C27 1.352(9) . ?
N5 C39 1.339(9) . ?
N5 C35 1.356(10) . ?
N6 C44 1.348(12) . ?
N6 C40 1.360(11) . ?
C1 C2 1.395(11) . ?
C1 H1 0.9300 . ?
C2 C3 1.374(11) . ?
C2 H2 0.9300 . ?
C3 C4 1.406(12) . ?
C3 H3 0.9300 . ?
C4 C5 1.367(11) . ?
C4 H4 0.9300 . ?
C5 C7 1.525(11) . ?
C6 C7 1.496(10) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.570(10) . ?
C8 C9 1.534(10) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C17 1.515(10) . ?
C9 C10 1.537(10) . ?
C10 C11 1.552(10) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.532(10) . ?
C11 C22 1.538(10) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.381(11) . ?
C13 H13 0.9300 . ?
C14 C15 1.377(12) . ?
C14 H14 0.9300 . ?
C15 C16 1.385(11) . ?
C15 H15 0.9300 . ?
C16 C17 1.390(11) . ?
C16 H16 0.9300 . ?
C18 C19 1.387(12) . ?
C18 H18 0.9300 . ?
C19 C20 1.368(14) . ?
C19 H19 0.9300 . ?
C20 C21 1.408(12) . ?
C20 H20 0.9300 . ?
C21 C22 1.377(11) . ?
C21 H21 0.9300 . ?
C23 C24 1.389(11) . ?
C23 H23 0.9300 . ?
C24 C25 1.378(12) . ?
C24 H24 0.9300 . ?
C25 C26 1.395(12) . ?
C25 H25 0.9300 . ?
C26 C27 1.385(11) . ?
C26 H26 0.9300 . ?
C27 C29 1.538(10) . ?
C28 C29 1.534(10) . ?
C28 H28B 0.9600 . ?
C28 H28A 0.9600 . ?
C28 H28C 0.9600 . ?
C29 C30 1.556(10) . ?
C30 C31 1.536(10) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C31 C39 1.532(10) . ?
C31 C32 1.542(10) . ?
C32 C33 1.542(11) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 C44 1.530(11) . ?
C33 C34 1.534(10) . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C35 C36 1.386(11) . ?
C35 H35 0.9300 . ?
C36 C37 1.395(12) . ?
C36 H36 0.9300 . ?
C37 C38 1.384(11) . ?
C37 H37 0.9300 . ?
C38 C39 1.388(11) . ?
C38 H38 0.9300 . ?
C40 C41 1.369(13) . ?
C40 H40 0.9300 . ?
C41 C42 1.359(16) . ?
C41 H41 0.9300 . ?
C42 C43 1.393(14) . ?
C42 H42 0.9300 . ?
C43 C44 1.407(12) . ?
C43 H43 0.9300 . ?
Cl3 C45 1.762(12) . ?
Cl4 C45 1.773(10) . ?
C45 H45A 0.9700 . ?
C45 H45B 0.9700 . ?

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
O4 Mn1 O1 101.3(2) . . ?
O4 Mn1 O2 169.1(2) . . ?
O1 Mn1 O2 89.5(2) . . ?
O4 Mn1 O5 90.6(2) . . ?
O1 Mn1 O5 167.9(2) . . ?
O2 Mn1 O5 78.72(19) . . ?
O4 Mn1 N1 92.9(2) . . ?
O1 Mn1 N1 77.5(2) . . ?
O2 Mn1 N1 91.3(2) . . ?
O5 Mn1 N1 99.6(2) . . ?
O4 Mn1 N4 77.4(2) . . ?
O1 Mn1 N4 92.6(2) . . ?
O2 Mn1 N4 100.5(2) . . ?
O5 Mn1 N4 92.4(2) . . ?
N1 Mn1 N4 164.6(2) . . ?
O4 Mn1 Mn2 129.70(16) . . ?
O1 Mn1 Mn2 129.03(16) . . ?
O2 Mn1 Mn2 39.58(14) . . ?
O5 Mn1 Mn2 39.13(15) . . ?
N1 Mn1 Mn2 97.24(16) . . ?
N4 Mn1 Mn2 98.14(15) . . ?
O3 Mn2 O6 92.4(2) . . ?
O3 Mn2 O5 168.4(2) . . ?
O6 Mn2 O5 94.1(2) . . ?
O3 Mn2 O2 94.2(2) . . ?
O6 Mn2 O2 168.5(2) . . ?
O5 Mn2 O2 80.97(19) . . ?
O3 Mn2 N2 91.5(2) . . ?
O6 Mn2 N2 93.6(2) . . ?
O5 Mn2 N2 97.5(2) . . ?
O2 Mn2 N2 76.9(2) . . ?
O3 Mn2 N5 93.8(2) . . ?
O6 Mn2 N5 91.7(2) . . ?
O5 Mn2 N5 76.5(2) . . ?
O2 Mn2 N5 97.2(2) . . ?
N2 Mn2 N5 172.28(18) . . ?
O3 Mn2 Mn1 133.64(15) . . ?
O6 Mn2 Mn1 133.95(16) . . ?
O5 Mn2 Mn1 40.62(15) . . ?
O2 Mn2 Mn1 40.35(14) . . ?
N2 Mn2 Mn1 86.53(16) . . ?
N5 Mn2 Mn1 85.75(15) . . ?
O3 Mn2 Mn3 45.86(15) . . ?
O6 Mn2 Mn3 46.55(16) . . ?
O5 Mn2 Mn3 139.69(15) . . ?
O2 Mn2 Mn3 139.33(15) . . ?
N2 Mn2 Mn3 94.12(16) . . ?
N5 Mn2 Mn3 93.61(16) . . ?
Mn1 Mn2 Mn3 179.17(6) . . ?
O3 Mn3 O6 73.47(16) . . ?
O3 Mn3 N6 102.0(2) . . ?
O6 Mn3 N6 69.2(2) . . ?
O3 Mn3 N3 70.2(2) . . ?
O6 Mn3 N3 102.1(2) . . ?
N6 Mn3 N3 170.1(2) . . ?
O3 Mn3 Cl1 158.19(16) . . ?
O6 Mn3 Cl1 100.03(14) . . ?
N6 Mn3 Cl1 94.67(17) . . ?
N3 Mn3 Cl1 91.50(18) . . ?
O3 Mn3 Cl2 97.83(16) . . ?
O6 Mn3 Cl2 156.71(17) . . ?
N6 Mn3 Cl2 92.3(2) . . ?
N3 Mn3 Cl2 94.77(18) . . ?
Cl1 Mn3 Cl2 95.38(11) . . ?
O3 Mn3 Mn2 36.70(12) . . ?
O6 Mn3 Mn2 36.78(12) . . ?
N6 Mn3 Mn2 84.53(17) . . ?
N3 Mn3 Mn2 85.65(16) . . ?
Cl1 Mn3 Mn2 133.65(7) . . ?
Cl2 Mn3 Mn2 130.97(10) . . ?
C7 O1 Mn1 114.3(4) . . ?
C9 O2 Mn2 112.8(4) . . ?
C9 O2 Mn1 125.5(4) . . ?
Mn2 O2 Mn1 100.1(2) . . ?
C11 O3 Mn2 123.2(4) . . ?
C11 O3 Mn3 118.6(4) . . ?
Mn2 O3 Mn3 97.4(2) . . ?
C29 O4 Mn1 114.2(4) . . ?
C31 O5 Mn2 114.3(4) . . ?
C31 O5 Mn1 124.0(4) . . ?
Mn2 O5 Mn1 100.2(2) . . ?
C33 O6 Mn2 123.0(4) . . ?
C33 O6 Mn3 119.1(4) . . ?
Mn2 O6 Mn3 96.7(2) . . ?
C1 N1 C5 120.6(6) . . ?
C1 N1 Mn1 131.5(5) . . ?
C5 N1 Mn1 107.8(5) . . ?
C13 N2 C17 120.0(7) . . ?
C13 N2 Mn2 130.0(5) . . ?
C17 N2 Mn2 109.9(5) . . ?
C18 N3 C22 118.5(7) . . ?
C18 N3 Mn3 122.7(6) . . ?
C22 N3 Mn3 118.7(5) . . ?
C23 N4 C27 119.7(6) . . ?
C23 N4 Mn1 133.5(5) . . ?
C27 N4 Mn1 106.5(4) . . ?
C39 N5 C35 119.7(7) . . ?
C39 N5 Mn2 110.2(5) . . ?
C35 N5 Mn2 130.0(5) . . ?
C44 N6 C40 118.8(8) . . ?
C44 N6 Mn3 119.8(5) . . ?
C40 N6 Mn3 121.2(6) . . ?
N1 C1 C2 121.9(7) . . ?
N1 C1 H1 119.1 . . ?
C2 C1 H1 119.1 . . ?
C3 C2 C1 117.9(7) . . ?
C3 C2 H2 121.0 . . ?
C1 C2 H2 121.0 . . ?
C2 C3 C4 119.5(8) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 119.4(8) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
N1 C5 C4 120.4(7) . . ?
N1 C5 C7 113.8(6) . . ?
C4 C5 C7 125.7(7) . . ?
C7 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C7 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O1 C7 C6 109.1(6) . . ?
O1 C7 C5 107.7(6) . . ?
C6 C7 C5 111.7(6) . . ?
O1 C7 C8 109.8(6) . . ?
C6 C7 C8 108.5(6) . . ?
C5 C7 C8 110.0(6) . . ?
C9 C8 C7 118.6(6) . . ?
C9 C8 H8A 107.7 . . ?
C7 C8 H8A 107.7 . . ?
C9 C8 H8B 107.7 . . ?
C7 C8 H8B 107.7 . . ?
H8A C8 H8B 107.1 . . ?
O2 C9 C17 109.8(6) . . ?
O2 C9 C8 107.2(6) . . ?
C17 C9 C8 113.8(6) . . ?
O2 C9 C10 106.3(6) . . ?
C17 C9 C10 108.7(6) . . ?
C8 C9 C10 110.7(6) . . ?
C9 C10 C11 119.8(6) . . ?
C9 C10 H10A 107.4 . . ?
C11 C10 H10A 107.4 . . ?
C9 C10 H10B 107.4 . . ?
C11 C10 H10B 107.4 . . ?
H10A C10 H10B 106.9 . . ?
O3 C11 C12 107.9(6) . . ?
O3 C11 C22 108.8(6) . . ?
C12 C11 C22 105.4(6) . . ?
O3 C11 C10 112.7(6) . . ?
C12 C11 C10 106.4(6) . . ?
C22 C11 C10 115.1(6) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C13 C14 121.0(7) . . ?
N2 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C15 C14 C13 119.7(8) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C16 119.5(8) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C15 C16 C17 118.7(7) . . ?
C15 C16 H16 120.7 . . ?
C17 C16 H16 120.7 . . ?
N2 C17 C16 121.0(7) . . ?
N2 C17 C9 113.0(6) . . ?
C16 C17 C9 125.8(7) . . ?
N3 C18 C19 123.4(8) . . ?
N3 C18 H18 118.3 . . ?
C19 C18 H18 118.3 . . ?
C20 C19 C18 119.3(8) . . ?
C20 C19 H19 120.3 . . ?
C18 C19 H19 120.3 . . ?
C19 C20 C21 117.3(8) . . ?
C19 C20 H20 121.3 . . ?
C21 C20 H20 121.3 . . ?
C22 C21 C20 120.6(8) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
N3 C22 C21 120.9(7) . . ?
N3 C22 C11 115.8(7) . . ?
C21 C22 C11 123.0(7) . . ?
N4 C23 C24 122.7(7) . . ?
N4 C23 H23 118.7 . . ?
C24 C23 H23 118.7 . . ?
C25 C24 C23 117.9(7) . . ?
C25 C24 H24 121.0 . . ?
C23 C24 H24 121.0 . . ?
C24 C25 C26 119.6(7) . . ?
C24 C25 H25 120.2 . . ?
C26 C25 H25 120.2 . . ?
C27 C26 C25 119.6(7) . . ?
C27 C26 H26 120.2 . . ?
C25 C26 H26 120.2 . . ?
N4 C27 C26 120.5(7) . . ?
N4 C27 C29 113.9(6) . . ?
C26 C27 C29 125.6(7) . . ?
C29 C28 H28B 109.5 . . ?
C29 C28 H28A 109.5 . . ?
H28B C28 H28A 109.5 . . ?
C29 C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
O4 C29 C28 108.2(6) . . ?
O4 C29 C27 107.4(6) . . ?
C28 C29 C27 111.7(6) . . ?
O4 C29 C30 111.9(6) . . ?
C28 C29 C30 107.8(6) . . ?
C27 C29 C30 109.8(6) . . ?
C31 C30 C29 118.9(6) . . ?
C31 C30 H30A 107.6 . . ?
C29 C30 H30A 107.6 . . ?
C31 C30 H30B 107.6 . . ?
C29 C30 H30B 107.6 . . ?
H30A C30 H30B 107.0 . . ?
O5 C31 C39 108.7(6) . . ?
O5 C31 C30 108.3(5) . . ?
C39 C31 C30 113.9(6) . . ?
O5 C31 C32 105.2(6) . . ?
C39 C31 C32 108.4(6) . . ?
C30 C31 C32 111.9(6) . . ?
C33 C32 C31 120.2(6) . . ?
C33 C32 H32A 107.3 . . ?
C31 C32 H32A 107.3 . . ?
C33 C32 H32B 107.3 . . ?
C31 C32 H32B 107.3 . . ?
H32A C32 H32B 106.9 . . ?
O6 C33 C44 108.1(6) . . ?
O6 C33 C34 107.0(6) . . ?
C44 C33 C34 106.6(6) . . ?
O6 C33 C32 112.8(6) . . ?
C44 C33 C32 115.6(6) . . ?
C34 C33 C32 106.2(6) . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
N5 C35 C36 121.3(7) . . ?
N5 C35 H35 119.4 . . ?
C36 C35 H35 119.4 . . ?
C35 C36 C37 118.8(7) . . ?
C35 C36 H36 120.6 . . ?
C37 C36 H36 120.6 . . ?
C38 C37 C36 119.4(7) . . ?
C38 C37 H37 120.3 . . ?
C36 C37 H37 120.3 . . ?
C37 C38 C39 118.9(7) . . ?
C37 C38 H38 120.6 . . ?
C39 C38 H38 120.6 . . ?
N5 C39 C38 121.8(7) . . ?
N5 C39 C31 113.6(6) . . ?
C38 C39 C31 124.6(7) . . ?
N6 C40 C41 122.4(9) . . ?
N6 C40 H40 118.8 . . ?
C41 C40 H40 118.8 . . ?
C42 C41 C40 118.4(9) . . ?
C42 C41 H41 120.8 . . ?
C40 C41 H41 120.8 . . ?
C41 C42 C43 121.9(9) . . ?
C41 C42 H42 119.1 . . ?
C43 C42 H42 119.1 . . ?
C42 C43 C44 116.6(10) . . ?
C42 C43 H43 121.7 . . ?
C44 C43 H43 121.7 . . ?
N6 C44 C43 121.8(8) . . ?
N6 C44 C33 116.5(7) . . ?
C43 C44 C33 121.5(8) . . ?
Cl3 C45 Cl4 111.3(5) . . ?
Cl3 C45 H45A 109.4 . . ?
Cl4 C45 H45A 109.4 . . ?
Cl3 C45 H45B 109.4 . . ?
Cl4 C45 H45B 109.4 . . ?
H45A C45 H45B 108.0 . . ?

_refine_diff_density_max         1.487
_refine_diff_density_min         -1.075
_refine_diff_density_rms         0.091



####################################################################### 
# 
# 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_T3ligand
_database_code_depnum_ccdc_archive 'CCDC 1529462'
_audit_update_record             
;
2017-03-18 deposited with the CCDC.
2017-06-12 downloaded from the CCDC.
;

_vrf_PLAT340_T3ligand            
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01195 Ang.  
RESPONSE: The crystal was of poor quality.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H25 N3 O3'
_chemical_formula_weight         379.45

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P n'
_space_group_name_Hall           'P -2yac'

_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+1/2, -y, z+1/2'

_cell_length_a                   8.7376(14)
_cell_length_b                   12.3604(19)
_cell_length_c                   9.2476(14)
_cell_angle_alpha                90
_cell_angle_beta                 108.002(8)
_cell_angle_gamma                90
_cell_volume                     949.8(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    3310
_cell_measurement_theta_min      3.3
_cell_measurement_theta_max      24.8

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_F_000             404
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.164
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private Communication'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Tube'
_diffrn_measurement_device_type  
; 
Rigaku CrystalClear-SM Expert 2.0 r15 
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 13.6612
_diffrn_reflns_number            11263
_diffrn_reflns_av_unetI/netI     0.0883
_diffrn_reflns_av_R_equivalents  0.0975
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.253
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_full        25.026
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             3333
_reflns_number_gt                2826
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.982
_reflns_Friedel_fraction_max     0.987
_reflns_Friedel_fraction_full    0.987

_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       
; 
Rigaku CrystalClear-SM Expert 2.0 r15 
;
_computing_cell_refinement       
; 
Rigaku CrystalClear-SM Expert 2.0 r15 
;
_computing_data_reduction        
; 
Rigaku CrystalClear-SM Expert 2.0 r15 
;
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
; 
 Dolomanov, O.V.; Bourhis, L.J.; Gildea, R.J.; Howard, J.A.K.; Puschmann, H., 
OLEX2: A complete structure solution, refinement and analysis program 
(2009). J. Appl. Cryst., 42, 339-341. 
;
_computing_publication_material  'SHELXL-2013/2 (Sheldrick, 2014)'
_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 

 The hydrogen atoms were first found in the difference map, then generated 
 geometrically and refined as riding atoms with C-H distances = 0.95- 0.99 
 Å and Uiso(H) = 1.2 times Ueq(C) for CH and CH2 groups and Uiso(H) 
 = 1.5 times Ueq(C) for CH3 groups. The only exceptions are H1, H2 and H3,
 which were found in the difference map and semi-freely refined with a distance 
 restraint of 0.85(2)A for O-H distances.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1570P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1011 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -1.0(10)
_chemical_absolute_configuration UNK
_refine_ls_number_reflns         3333
_refine_ls_number_parameters     264
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.1102
_refine_ls_R_factor_gt           0.0980
_refine_ls_wR_factor_ref         0.2438
_refine_ls_wR_factor_gt          0.2348
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.093
_refine_ls_shift/su_max          0.055
_refine_ls_shift/su_mean         0.013

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
O1 O 0.7927(7) 0.4400(5) 0.6686(6) 0.0351(14) Uani 1 1 d D . . . .
H1 H 0.874(8) 0.480(6) 0.676(11) 0.04(3) Uiso 1 1 d D . . . .
O2 O 0.6176(7) 0.2978(5) 0.7520(6) 0.0292(13) Uani 1 1 d D . . . .
H2 H 0.698(10) 0.341(8) 0.767(15) 0.08(4) Uiso 1 1 d D . . . .
O3 O 0.3960(7) 0.2157(5) 0.8714(6) 0.0330(14) Uani 1 1 d D . . . .
H3 H 0.4791 0.2527 0.8803 0.050 Uiso 1 1 calc DR U . . .
N1 N 0.5954(8) 0.4592(6) 0.2581(8) 0.0329(16) Uani 1 1 d . . . . .
N2 N 0.4461(8) 0.2424(5) 0.3477(7) 0.0276(15) Uani 1 1 d . . . . .
N3 N 0.3088(8) 0.0585(5) 0.5225(8) 0.0293(15) Uani 1 1 d . . . . .
C1 C 0.6241(11) 0.4211(7) 0.1300(9) 0.034(2) Uani 1 1 d . . . . .
H1A H 0.5487 0.4379 0.0341 0.040 Uiso 1 1 calc R U . . .
C2 C 0.7533(11) 0.3612(7) 0.1323(9) 0.036(2) Uani 1 1 d . . . . .
H2A H 0.7686 0.3373 0.0401 0.044 Uiso 1 1 calc R U . . .
C3 C 0.8625(11) 0.3351(7) 0.2693(10) 0.035(2) Uani 1 1 d . . . . .
H3A H 0.9541 0.2922 0.2739 0.043 Uiso 1 1 calc R U . . .
C4 C 0.8366(10) 0.3731(6) 0.4038(9) 0.0258(17) Uani 1 1 d . . . . .
H4 H 0.9125 0.3576 0.4999 0.031 Uiso 1 1 calc R U . . .
C5 C 0.7022(10) 0.4323(6) 0.3952(9) 0.0262(17) Uani 1 1 d . . . . .
C6 C 0.6580(11) 0.5980(7) 0.5300(11) 0.036(2) Uani 1 1 d . . . . .
H6A H 0.7531 0.6270 0.5086 0.055 Uiso 1 1 calc R U . . .
H6B H 0.6541 0.6257 0.6282 0.055 Uiso 1 1 calc R U . . .
H6C H 0.5608 0.6205 0.4497 0.055 Uiso 1 1 calc R U . . .
C7 C 0.6672(10) 0.4733(6) 0.5358(9) 0.0308(19) Uani 1 1 d . . . . .
C8 C 0.5087(10) 0.4298(6) 0.5517(10) 0.0309(18) Uani 1 1 d . . . . .
H8A H 0.4248 0.4379 0.4520 0.037 Uiso 1 1 calc R U . . .
H8B H 0.4775 0.4770 0.6245 0.037 Uiso 1 1 calc R U . . .
C9 C 0.5043(9) 0.3122(6) 0.6039(8) 0.0232(17) Uani 1 1 d . . . . .
C10 C 0.3369(9) 0.2890(6) 0.6158(8) 0.0240(16) Uani 1 1 d . . . . .
H10A H 0.2636 0.2767 0.5116 0.029 Uiso 1 1 calc R U . . .
H10B H 0.2993 0.3551 0.6549 0.029 Uiso 1 1 calc R U . . .
C11 C 0.3173(9) 0.1938(6) 0.7147(8) 0.0241(16) Uani 1 1 d . . . . .
C12 C 0.1388(10) 0.1841(7) 0.7020(10) 0.0336(19) Uani 1 1 d . . . . .
H12A H 0.1256 0.1301 0.7748 0.050 Uiso 1 1 calc R U . . .
H12B H 0.0775 0.1618 0.5986 0.050 Uiso 1 1 calc R U . . .
H12C H 0.0991 0.2543 0.7244 0.050 Uiso 1 1 calc R U . . .
C13 C 0.4766(11) 0.1794(6) 0.2417(9) 0.0311(19) Uani 1 1 d . . . . .
H13 H 0.4082 0.1847 0.1397 0.037 Uiso 1 1 calc R U . . .
C14 C 0.6022(12) 0.1077(6) 0.2744(9) 0.035(2) Uani 1 1 d . . . . .
H14 H 0.6212 0.0650 0.1962 0.042 Uiso 1 1 calc R U . . .
C15 C 0.7000(11) 0.0984(6) 0.4216(10) 0.032(2) Uani 1 1 d . . . . .
H15 H 0.7861 0.0479 0.4467 0.039 Uiso 1 1 calc R U . . .
C16 C 0.6728(10) 0.1628(6) 0.5333(9) 0.0287(18) Uani 1 1 d . . . . .
H16 H 0.7395 0.1579 0.6360 0.034 Uiso 1 1 calc R U . . .
C17 C 0.5450(9) 0.2348(6) 0.4907(8) 0.0237(16) Uani 1 1 d . . . . .
C18 C 0.3614(12) -0.0318(8) 0.4741(11) 0.041(2) Uani 1 1 d . . . . .
H18 H 0.3147 -0.0521 0.3707 0.049 Uiso 1 1 calc R U . . .
C19 C 0.4811(12) -0.0976(7) 0.5671(10) 0.036(2) Uani 1 1 d . . . . .
H19 H 0.5205 -0.1586 0.5271 0.043 Uiso 1 1 calc R U . . .
C20 C 0.5394(11) -0.0718(7) 0.7165(11) 0.039(2) Uani 1 1 d . . . . .
H20 H 0.6155 -0.1177 0.7848 0.047 Uiso 1 1 calc R U . . .
C21 C 0.4877(9) 0.0217(7) 0.7689(9) 0.0297(18) Uani 1 1 d . . . . .
H21 H 0.5296 0.0410 0.8731 0.036 Uiso 1 1 calc R U . . .
C22 C 0.3746(10) 0.0871(6) 0.6690(9) 0.0271(17) Uani 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.431(10) . ?
O1 H1 0.85(3) . ?
O2 C9 1.432(9) . ?
O2 H2 0.86(3) . ?
O3 C11 1.425(9) . ?
O3 H3 0.8400 . ?
N1 C5 1.364(10) . ?
N1 C1 1.368(11) . ?
N2 C13 1.342(10) . ?
N2 C17 1.341(10) . ?
N3 C18 1.336(12) . ?
N3 C22 1.345(10) . ?
C1 C2 1.345(13) . ?
C1 H1A 0.9500 . ?
C2 C3 1.369(12) . ?
C2 H2A 0.9500 . ?
C3 C4 1.412(11) . ?
C3 H3A 0.9500 . ?
C4 C5 1.365(11) . ?
C4 H4 0.9500 . ?
C5 C7 1.512(11) . ?
C6 C7 1.543(11) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.535(11) . ?
C8 C9 1.535(11) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.528(10) . ?
C9 C17 1.539(11) . ?
C10 C11 1.532(10) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C22 1.516(11) . ?
C11 C12 1.532(11) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.370(13) . ?
C13 H13 0.9500 . ?
C14 C15 1.370(13) . ?
C14 H14 0.9500 . ?
C15 C16 1.382(11) . ?
C15 H15 0.9500 . ?
C16 C17 1.387(11) . ?
C16 H16 0.9500 . ?
C18 C19 1.393(14) . ?
C18 H18 0.9500 . ?
C19 C20 1.355(13) . ?
C19 H19 0.9500 . ?
C20 C21 1.381(12) . ?
C20 H20 0.9500 . ?
C21 C22 1.386(11) . ?
C21 H21 0.9500 . ?

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
C7 O1 H1 108(7) . . ?
C9 O2 H2 112(9) . . ?
C11 O3 H3 109.5 . . ?
C5 N1 C1 117.7(7) . . ?
C13 N2 C17 117.9(7) . . ?
C18 N3 C22 118.2(8) . . ?
C2 C1 N1 123.6(8) . . ?
C2 C1 H1A 118.2 . . ?
N1 C1 H1A 118.2 . . ?
C1 C2 C3 119.1(7) . . ?
C1 C2 H2A 120.5 . . ?
C3 C2 H2A 120.5 . . ?
C2 C3 C4 118.8(8) . . ?
C2 C3 H3A 120.6 . . ?
C4 C3 H3A 120.6 . . ?
C5 C4 C3 119.8(8) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
N1 C5 C4 120.9(7) . . ?
N1 C5 C7 117.1(7) . . ?
C4 C5 C7 121.9(7) . . ?
C7 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C7 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O1 C7 C5 109.7(6) . . ?
O1 C7 C8 106.9(6) . . ?
C5 C7 C8 113.2(6) . . ?
O1 C7 C6 109.6(7) . . ?
C5 C7 C6 109.1(6) . . ?
C8 C7 C6 108.3(7) . . ?
C7 C8 C9 118.2(7) . . ?
C7 C8 H8A 107.8 . . ?
C9 C8 H8A 107.8 . . ?
C7 C8 H8B 107.8 . . ?
C9 C8 H8B 107.8 . . ?
H8A C8 H8B 107.1 . . ?
O2 C9 C10 107.6(6) . . ?
O2 C9 C8 110.0(6) . . ?
C10 C9 C8 108.5(6) . . ?
O2 C9 C17 109.7(6) . . ?
C10 C9 C17 111.1(6) . . ?
C8 C9 C17 110.0(6) . . ?
C9 C10 C11 118.3(6) . . ?
C9 C10 H10A 107.7 . . ?
C11 C10 H10A 107.7 . . ?
C9 C10 H10B 107.7 . . ?
C11 C10 H10B 107.7 . . ?
H10A C10 H10B 107.1 . . ?
O3 C11 C22 110.6(6) . . ?
O3 C11 C12 104.7(6) . . ?
C22 C11 C12 109.1(6) . . ?
O3 C11 C10 110.7(6) . . ?
C22 C11 C10 113.2(6) . . ?
C12 C11 C10 108.2(6) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C13 C14 122.7(8) . . ?
N2 C13 H13 118.6 . . ?
C14 C13 H13 118.6 . . ?
C15 C14 C13 119.0(7) . . ?
C15 C14 H14 120.5 . . ?
C13 C14 H14 120.5 . . ?
C14 C15 C16 119.8(8) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C17 C16 C15 117.8(8) . . ?
C17 C16 H16 121.1 . . ?
C15 C16 H16 121.1 . . ?
N2 C17 C16 122.8(7) . . ?
N2 C17 C9 114.4(6) . . ?
C16 C17 C9 122.7(7) . . ?
N3 C18 C19 123.5(9) . . ?
N3 C18 H18 118.3 . . ?
C19 C18 H18 118.3 . . ?
C20 C19 C18 117.8(8) . . ?
C20 C19 H19 121.1 . . ?
C18 C19 H19 121.1 . . ?
C19 C20 C21 119.6(8) . . ?
C19 C20 H20 120.2 . . ?
C21 C20 H20 120.2 . . ?
C22 C21 C20 119.9(8) . . ?
C22 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
N3 C22 C21 120.8(8) . . ?
N3 C22 C11 115.7(7) . . ?
C21 C22 C11 123.4(7) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N1 0.85(3) 1.99(5) 2.807(9) 160(9) 2_565
O2 H2 O1 0.86(3) 1.86(8) 2.598(8) 142(12) .
O3 H3 O2 0.84 2.02 2.706(8) 138.6 .

_refine_diff_density_max         0.768
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.107

####################################################################### 
# 
# 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_mini-15089-rdl
_database_code_depnum_ccdc_archive 'CCDC 1529459'
_audit_update_record             
;
2017-03-18 deposited with the CCDC.
2017-06-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H18 N2 O2, H2 O'
_chemical_formula_sum            'C15 H20 N2 O3'
_chemical_formula_weight         276.33

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.7831(7)
_cell_length_b                   9.0271(6)
_cell_length_c                   16.4023(12)
_cell_angle_alpha                90
_cell_angle_beta                 103.691(7)
_cell_angle_gamma                90
_cell_volume                     1407.38(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    11038
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      30.6

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.091
_shelx_estimated_absorpt_T_min   0.964
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.892
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Tube'
_diffrn_measurement_device_type  'Rigaku Mercury275R CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 6.8
_diffrn_reflns_number            12383
_diffrn_reflns_av_unetI/netI     0.0427
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.112
_diffrn_reflns_theta_max         30.505
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4243
_reflns_number_gt                3275
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
; 
 Dolomanov, O.V.; Bourhis, L.J.; Gildea, R.J.; Howard, J.A.K.; Puschmann, H.,
OLEX2: A complete structure solution, refinement and analysis program
(2009). J. Appl. Cryst., 42, 339-341.
;
_computing_publication_material  'CIFTAB-2013/2 (Sheldrick, 2014)'
_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.

 The hydrogen atoms were first found in the difference map, then generated
 geometrically and refined as riding atoms with C-H distances = 0.95- 0.99
 Å and Uiso(H) = 1.2 times Ueq(C) for CH and CH2 groups and Uiso(H)
 = 1.5 times Ueq(C) for CH3 groups. The only exceptions are H1, H2, H3A, and H3B
 which were found in the difference map and semi-freely refined with a distance
 restraint of 0.85(2) Å for O-H distances.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0483P)²+0.5393P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     SHELXT
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4243
_refine_ls_number_parameters     199
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0774
_refine_ls_R_factor_gt           0.0540
_refine_ls_wR_factor_ref         0.1170
_refine_ls_wR_factor_gt          0.1089
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.60788(10) 0.40513(10) 0.33795(6) 0.0161(2) Uani 1 1 d D . . . .
H1 H 0.5190(16) 0.424(2) 0.3182(13) 0.043(6) Uiso 1 1 d D . . . .
O2 O 0.82170(11) 0.21863(10) 0.35668(6) 0.0154(2) Uani 1 1 d . . . . .
H2 H 0.734(2) 0.247(2) 0.3445(13) 0.040(6) Uiso 1 1 d . . . . .
N1 N 0.69613(13) 0.79495(12) 0.36886(7) 0.0174(2) Uani 1 1 d . . . . .
N2 N 0.79975(12) 0.22783(12) 0.19245(7) 0.0154(2) Uani 1 1 d . . . . .
C1 C 0.68319(16) 0.90133(15) 0.42383(9) 0.0197(3) Uani 1 1 d . . . . .
H1A H 0.7057 1.0001 0.4119 0.024 Uiso 1 1 calc R U . . .
C2 C 0.63913(15) 0.87562(16) 0.49654(9) 0.0191(3) Uani 1 1 d . . . . .
H2A H 0.6325 0.9544 0.5338 0.023 Uiso 1 1 calc R U . . .
C3 C 0.60489(15) 0.73213(16) 0.51377(9) 0.0195(3) Uani 1 1 d . . . . .
H3 H 0.5732 0.7104 0.5629 0.023 Uiso 1 1 calc R U . . .
C4 C 0.61774(15) 0.62080(15) 0.45790(8) 0.0169(3) Uani 1 1 d . . . . .
H4 H 0.5948 0.5214 0.4684 0.020 Uiso 1 1 calc R U . . .
C5 C 0.66449(13) 0.65564(14) 0.38620(8) 0.0131(2) Uani 1 1 d . . . . .
C6 C 0.65158(15) 0.58204(15) 0.23576(8) 0.0170(3) Uani 1 1 d . . . . .
H6A H 0.6551 0.4969 0.1993 0.025 Uiso 1 1 calc R U . . .
H6B H 0.7186 0.6575 0.2269 0.025 Uiso 1 1 calc R U . . .
H6C H 0.5564 0.6237 0.2224 0.025 Uiso 1 1 calc R U . . .
C7 C 0.69013(14) 0.53212(14) 0.32740(8) 0.0131(2) Uani 1 1 d . . . . .
C8 C 0.84663(14) 0.48765(14) 0.35904(8) 0.0138(3) Uani 1 1 d . . . . .
H8A H 0.9041 0.5668 0.3419 0.017 Uiso 1 1 calc R U . . .
H8B H 0.8685 0.4877 0.4211 0.017 Uiso 1 1 calc R U . . .
C9 C 0.89790(14) 0.33813(14) 0.33101(8) 0.0129(2) Uani 1 1 d . . . . .
C10 C 1.05163(14) 0.31636(15) 0.37754(8) 0.0170(3) Uani 1 1 d . . . . .
H10A H 1.0591 0.3174 0.4382 0.026 Uiso 1 1 calc R U . . .
H10B H 1.1088 0.3966 0.3628 0.026 Uiso 1 1 calc R U . . .
H10C H 1.0855 0.2211 0.3615 0.026 Uiso 1 1 calc R U . . .
C11 C 0.79076(15) 0.21846(15) 0.10953(8) 0.0188(3) Uani 1 1 d . . . . .
H11 H 0.7284 0.1472 0.0782 0.023 Uiso 1 1 calc R U . . .
C12 C 0.86674(16) 0.30617(16) 0.06714(9) 0.0201(3) Uani 1 1 d . . . . .
H12 H 0.8576 0.2950 0.0085 0.024 Uiso 1 1 calc R U . . .
C13 C 0.95689(15) 0.41123(15) 0.11295(9) 0.0186(3) Uani 1 1 d . . . . .
H13 H 1.0111 0.4737 0.0862 0.022 Uiso 1 1 calc R U . . .
C14 C 0.96650(15) 0.42357(15) 0.19826(8) 0.0160(3) Uani 1 1 d . . . . .
H14 H 1.0270 0.4953 0.2306 0.019 Uiso 1 1 calc R U . . .
C15 C 0.88672(13) 0.32985(14) 0.23632(8) 0.0127(2) Uani 1 1 d . . . . .
O3 O 0.66649(11) -0.04032(11) 0.21635(6) 0.0179(2) Uani 1 1 d D . . . .
H3A H 0.692(2) -0.089(2) 0.2632(11) 0.046(6) Uiso 1 1 d D . . . .
H3B H 0.709(2) 0.0455(19) 0.2214(13) 0.046(6) Uiso 1 1 d D . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.4344(16) . ?
O1 H1 0.870(15) . ?
O2 C9 1.4301(15) . ?
O2 H2 0.87(2) . ?
N1 C5 1.3416(17) . ?
N1 C1 1.3435(17) . ?
N2 C15 1.3417(17) . ?
N2 C11 1.3446(17) . ?
C1 C2 1.380(2) . ?
C1 H1A 0.9500 . ?
C2 C3 1.384(2) . ?
C2 H2A 0.9500 . ?
C3 C4 1.3855(19) . ?
C3 H3 0.9500 . ?
C4 C5 1.3950(18) . ?
C4 H4 0.9500 . ?
C5 C7 1.5333(18) . ?
C6 C7 1.5285(17) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.5487(18) . ?
C8 C9 1.5472(18) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.5297(18) . ?
C9 C15 1.5328(17) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.381(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.389(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.3847(18) . ?
C13 H13 0.9500 . ?
C14 C15 1.3947(18) . ?
C14 H14 0.9500 . ?
O3 H3A 0.869(15) . ?
O3 H3B 0.874(15) . ?

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
C7 O1 H1 109.6(14) . . ?
C9 O2 H2 105.6(14) . . ?
C5 N1 C1 117.68(12) . . ?
C15 N2 C11 117.84(12) . . ?
N1 C1 C2 123.92(13) . . ?
N1 C1 H1A 118.0 . . ?
C2 C1 H1A 118.0 . . ?
C1 C2 C3 118.29(13) . . ?
C1 C2 H2A 120.9 . . ?
C3 C2 H2A 120.9 . . ?
C2 C3 C4 118.67(13) . . ?
C2 C3 H3 120.7 . . ?
C4 C3 H3 120.7 . . ?
C3 C4 C5 119.55(12) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
N1 C5 C4 121.88(12) . . ?
N1 C5 C7 117.91(11) . . ?
C4 C5 C7 120.10(11) . . ?
C7 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C7 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O1 C7 C6 109.84(10) . . ?
O1 C7 C5 108.98(10) . . ?
C6 C7 C5 111.42(10) . . ?
O1 C7 C8 106.90(10) . . ?
C6 C7 C8 113.59(11) . . ?
C5 C7 C8 105.88(10) . . ?
C9 C8 C7 119.39(10) . . ?
C9 C8 H8A 107.5 . . ?
C7 C8 H8A 107.5 . . ?
C9 C8 H8B 107.5 . . ?
C7 C8 H8B 107.5 . . ?
H8A C8 H8B 107.0 . . ?
O2 C9 C10 106.00(10) . . ?
O2 C9 C15 110.15(10) . . ?
C10 C9 C15 108.98(11) . . ?
O2 C9 C8 110.02(10) . . ?
C10 C9 C8 108.26(10) . . ?
C15 C9 C8 113.16(10) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C11 C12 123.99(13) . . ?
N2 C11 H11 118.0 . . ?
C12 C11 H11 118.0 . . ?
C11 C12 C13 117.89(12) . . ?
C11 C12 H12 121.1 . . ?
C13 C12 H12 121.1 . . ?
C14 C13 C12 118.97(13) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C13 C14 C15 119.48(13) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
N2 C15 C14 121.83(12) . . ?
N2 C15 C9 117.45(11) . . ?
C14 C15 C9 120.71(11) . . ?
H3A O3 H3B 110(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 -0.2(2) . . . . ?
N1 C1 C2 C3 -0.6(2) . . . . ?
C1 C2 C3 C4 0.7(2) . . . . ?
C2 C3 C4 C5 0.0(2) . . . . ?
C1 N1 C5 C4 0.9(2) . . . . ?
C1 N1 C5 C7 -175.27(12) . . . . ?
C3 C4 C5 N1 -0.8(2) . . . . ?
C3 C4 C5 C7 175.26(12) . . . . ?
N1 C5 C7 O1 -160.27(11) . . . . ?
C4 C5 C7 O1 23.49(16) . . . . ?
N1 C5 C7 C6 -38.91(16) . . . . ?
C4 C5 C7 C6 144.85(12) . . . . ?
N1 C5 C7 C8 85.05(14) . . . . ?
C4 C5 C7 C8 -91.19(14) . . . . ?
O1 C7 C8 C9 46.53(14) . . . . ?
C6 C7 C8 C9 -74.78(14) . . . . ?
C5 C7 C8 C9 162.63(11) . . . . ?
C7 C8 C9 O2 -59.40(14) . . . . ?
C7 C8 C9 C10 -174.82(11) . . . . ?
C7 C8 C9 C15 64.28(15) . . . . ?
C15 N2 C11 C12 0.8(2) . . . . ?
N2 C11 C12 C13 -0.6(2) . . . . ?
C11 C12 C13 C14 -0.1(2) . . . . ?
C12 C13 C14 C15 0.5(2) . . . . ?
C11 N2 C15 C14 -0.30(19) . . . . ?
C11 N2 C15 C9 -179.11(12) . . . . ?
C13 C14 C15 N2 -0.3(2) . . . . ?
C13 C14 C15 C9 178.43(12) . . . . ?
O2 C9 C15 N2 6.81(16) . . . . ?
C10 C9 C15 N2 122.70(13) . . . . ?
C8 C9 C15 N2 -116.80(13) . . . . ?
O2 C9 C15 C14 -172.02(11) . . . . ?
C10 C9 C15 C14 -56.13(16) . . . . ?
C8 C9 C15 C14 64.37(16) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O3 0.870(15) 1.797(15) 2.6662(14) 176(2) 2_655
O2 H2 O1 0.87(2) 1.87(2) 2.6458(14) 146.3(19) .
O3 H3A N1 0.869(15) 2.017(16) 2.8652(15) 165(2) 1_545
O3 H3B N2 0.874(15) 1.980(16) 2.8204(15) 161(2) .

_refine_diff_density_max         0.426
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.053

####################################################################### 
# 
# 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_007-17059-cot3-2_sq
_database_code_depnum_ccdc_archive 'CCDC 1552433'
_audit_update_record             
;
2017-05-25 deposited with the CCDC.
2017-06-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C44 H44 Co2 N6 O6'
_chemical_formula_weight         870.71

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'
Co Co -2.3653 3.6143 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.4079(2)
_cell_length_b                   12.0756(2)
_cell_length_c                   19.9987(14)
_cell_angle_alpha                90
_cell_angle_beta                 93.505(7)
_cell_angle_gamma                90
_cell_volume                     2026.68(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    33266
_cell_measurement_theta_min      2.2
_cell_measurement_theta_max      66.6

_exptl_crystal_description       Plate
_exptl_crystal_colour            Brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_F_000             904
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    6.873
_shelx_estimated_absorpt_T_min   0.340
_shelx_estimated_absorpt_T_max   0.546
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.852
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private Communication'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Rotating Anode'
_diffrn_measurement_device_type  
; 
Rigaku CrystalClear-SM Expert 2.0 r15 
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 22.2222
_diffrn_reflns_number            62645
_diffrn_reflns_av_unetI/netI     0.0743
_diffrn_reflns_av_R_equivalents  0.1705
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         4.279
_diffrn_reflns_theta_max         66.599
_diffrn_reflns_theta_full        66.599
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3562
_reflns_number_gt                2519
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 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. 
;

_computing_data_collection       
; 
Rigaku CrystalClear-SM Expert 2.0 r15 
;
_computing_cell_refinement       
; 
Rigaku CrystalClear-SM Expert 2.0 r15 
;
_computing_data_reduction        
; 
Rigaku CrystalClear-SM Expert 2.0 r15 
;
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
; 
Dolomanov, O.V.; Bourhis, L.J.; Gildea, R.J.; Howard, J.A.K.; Puschmann, H., 
OLEX2: A complete structure solution, refinement and analysis program 
(2009). J. Appl. Cryst., 42, 339-341. 
;
_computing_publication_material  'SHELXL-2013/2 (Sheldrick, 2014)'
_refine_special_details          
; 
Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 

The hydrogen atoms were first found in the difference map, then generated 
geometrically and refined as riding atoms with C-H distances = 0.95 - 0.99 
angstroms and Uiso(H) = 1.2 times Ueq(C) for CH and CH2 groups and Uiso(H) 
= 1.5 times Ueq(C) for CH3 groups. 

The program SQUEEZE was used to compensate for the contribution of disordered 
solvents contained in voids within the crystal lattice from the diffraction 
intensities. This procedure was applied to the data file and the submitted 
model is based on the solvent removed data. Based on the total electron density 
found in the voids (78 e/A3), it is likely that ~8 water molecules 
molecules are present in the unit cell. See "_platon_squeeze_details" in this .cif 
for more information. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1603P)²+0.3795P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3562
_refine_ls_number_parameters     264
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1063
_refine_ls_R_factor_gt           0.0793
_refine_ls_wR_factor_ref         0.2592
_refine_ls_wR_factor_gt          0.2055
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.092
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.55684(10) 0.40176(7) 0.53723(4) 0.0307(3) Uani 1 1 d . . . . .
O3 O 0.4625(5) 0.6575(3) 0.37445(19) 0.0371(9) Uani 1 1 d . . . . .
O2 O 0.5767(4) 0.4736(3) 0.44912(19) 0.0327(9) Uani 1 1 d . . . . .
O1 O 0.6933(5) 0.2888(3) 0.50892(19) 0.0336(9) Uani 1 1 d . . . . .
N2 N 0.2799(5) 0.5008(4) 0.4283(2) 0.0324(11) Uani 1 1 d . . . . .
N1 N 0.3918(6) 0.2965(4) 0.5117(2) 0.0340(11) Uani 1 1 d . . . . .
N3 N 0.2982(6) 0.4972(4) 0.2301(2) 0.0422(13) Uani 1 1 d . . . . .
C10 C 0.3344(7) 0.4134(4) 0.3924(3) 0.0277(12) Uani 1 1 d . . . . .
C5 C 0.4431(6) 0.2103(5) 0.4743(3) 0.0314(13) Uani 1 1 d . . . . .
C19 C 0.5154(7) 0.4156(5) 0.3910(3) 0.0315(13) Uani 1 1 d . . . . .
C9 C 0.2285(7) 0.3435(5) 0.3596(3) 0.0347(13) Uani 1 1 d . . . . .
H9 H 0.2663 0.2854 0.3328 0.042 Uiso 1 1 calc R U . . .
C15 C 0.3101(7) 0.5744(5) 0.2793(3) 0.0374(14) Uani 1 1 d . . . . .
C6 C 0.1222(7) 0.5148(5) 0.4342(3) 0.0332(13) Uani 1 1 d . . . . .
H6 H 0.0863 0.5749 0.4600 0.040 Uiso 1 1 calc R U . . .
C17 C 0.6098(7) 0.2322(5) 0.4547(3) 0.0371(14) Uani 1 1 d . . . . .
C8 C 0.0653(7) 0.3569(5) 0.3653(3) 0.0379(14) Uani 1 1 d . . . . .
H8 H -0.0087 0.3075 0.3434 0.045 Uiso 1 1 calc R U . . .
C14 C 0.1795(8) 0.6420(5) 0.2935(3) 0.0410(15) Uani 1 1 d . . . . .
H14 H 0.1895 0.6971 0.3274 0.049 Uiso 1 1 calc R U . . .
C2 C 0.1406(8) 0.2096(6) 0.5185(3) 0.0453(16) Uani 1 1 d . . . . .
H2 H 0.0370 0.2103 0.5349 0.054 Uiso 1 1 calc R U . . .
C7 C 0.0126(7) 0.4442(5) 0.4039(3) 0.0362(13) Uani 1 1 d . . . . .
H7 H -0.0980 0.4546 0.4090 0.043 Uiso 1 1 calc R U . . .
C18 C 0.5991(7) 0.3024(5) 0.3895(3) 0.0338(13) Uani 1 1 d . . . . .
H18A H 0.7090 0.3149 0.3760 0.041 Uiso 1 1 calc R U . . .
H18B H 0.5435 0.2574 0.3539 0.041 Uiso 1 1 calc R U . . .
C21 C 0.4741(7) 0.5931(5) 0.3165(3) 0.0350(14) Uani 1 1 d . . . . .
C20 C 0.5608(7) 0.4822(5) 0.3298(3) 0.0335(13) Uani 1 1 d . . . . .
H20A H 0.5416 0.4349 0.2896 0.040 Uiso 1 1 calc R U . . .
H20B H 0.6767 0.4973 0.3346 0.040 Uiso 1 1 calc R U . . .
C11 C 0.1554(8) 0.4826(6) 0.1966(3) 0.0437(15) Uani 1 1 d . . . . .
H11 H 0.1464 0.4266 0.1632 0.052 Uiso 1 1 calc R U . . .
C1 C 0.2450(7) 0.2946(5) 0.5337(3) 0.0371(14) Uani 1 1 d . . . . .
H1 H 0.2117 0.3539 0.5608 0.044 Uiso 1 1 calc R U . . .
C4 C 0.3449(8) 0.1225(5) 0.4572(3) 0.0406(15) Uani 1 1 d . . . . .
H4 H 0.3815 0.0627 0.4313 0.049 Uiso 1 1 calc R U . . .
C22 C 0.5718(7) 0.6604(5) 0.2685(3) 0.0408(15) Uani 1 1 d . . . . .
H22A H 0.5164 0.7300 0.2572 0.061 Uiso 1 1 calc R U . . .
H22B H 0.5843 0.6177 0.2275 0.061 Uiso 1 1 calc R U . . .
H22C H 0.6770 0.6767 0.2901 0.061 Uiso 1 1 calc R U . . .
C12 C 0.0214(8) 0.5446(6) 0.2081(3) 0.0469(16) Uani 1 1 d . . . . .
H12 H -0.0773 0.5320 0.1836 0.056 Uiso 1 1 calc R U . . .
C16 C 0.7003(8) 0.1267(5) 0.4401(3) 0.0413(15) Uani 1 1 d . . . . .
H16A H 0.8095 0.1454 0.4297 0.062 Uiso 1 1 calc R U . . .
H16B H 0.6469 0.0886 0.4017 0.062 Uiso 1 1 calc R U . . .
H16C H 0.7029 0.0781 0.4794 0.062 Uiso 1 1 calc R U . . .
C3 C 0.1875(8) 0.1233(6) 0.4791(4) 0.0433(15) Uani 1 1 d . . . . .
H3 H 0.1155 0.0651 0.4668 0.052 Uiso 1 1 calc R U . . .
C13 C 0.0374(8) 0.6261(6) 0.2569(3) 0.0488(17) Uani 1 1 d . . . . .
H13 H -0.0514 0.6717 0.2652 0.059 Uiso 1 1 calc 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 O1 1.891(4) . ?
Co1 N2 1.905(5) 3_666 ?
Co1 O2 1.907(4) 3_666 ?
Co1 O3 1.922(4) 3_666 ?
Co1 N1 1.927(5) . ?
Co1 O2 1.980(4) . ?
Co1 Co1 2.9302(17) 3_666 ?
O3 C21 1.404(7) . ?
O3 Co1 1.922(4) 3_666 ?
O2 C19 1.426(7) . ?
O2 Co1 1.907(4) 3_666 ?
O1 C17 1.429(7) . ?
N2 C6 1.350(7) . ?
N2 C10 1.371(7) . ?
N2 Co1 1.905(5) 3_666 ?
N1 C1 1.336(7) . ?
N1 C5 1.367(7) . ?
N3 C11 1.350(8) . ?
N3 C15 1.355(8) . ?
C10 C9 1.365(8) . ?
C10 C19 1.524(8) . ?
C5 C4 1.375(8) . ?
C5 C17 1.502(8) . ?
C19 C20 1.533(8) . ?
C19 C18 1.539(8) . ?
C9 C8 1.394(8) . ?
C9 H9 0.9500 . ?
C15 C14 1.411(9) . ?
C15 C21 1.543(8) . ?
C6 C7 1.370(8) . ?
C6 H6 0.9500 . ?
C17 C16 1.522(8) . ?
C17 C18 1.552(8) . ?
C8 C7 1.394(8) . ?
C8 H8 0.9500 . ?
C14 C13 1.377(9) . ?
C14 H14 0.9500 . ?
C2 C1 1.372(9) . ?
C2 C3 1.378(10) . ?
C2 H2 0.9500 . ?
C7 H7 0.9500 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C21 C22 1.535(8) . ?
C21 C20 1.540(8) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C11 C12 1.384(9) . ?
C11 H11 0.9500 . ?
C1 H1 0.9500 . ?
C4 C3 1.420(9) . ?
C4 H4 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C12 C13 1.386(10) . ?
C12 H12 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C3 H3 0.9500 . ?
C13 H13 0.9500 . ?

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 N2 96.72(18) . 3_666 ?
O1 Co1 O2 170.12(17) . 3_666 ?
N2 Co1 O2 83.02(18) 3_666 3_666 ?
O1 Co1 O3 95.37(17) . 3_666 ?
N2 Co1 O3 89.80(19) 3_666 3_666 ?
O2 Co1 O3 94.50(17) 3_666 3_666 ?
O1 Co1 N1 83.41(19) . . ?
N2 Co1 N1 173.91(19) 3_666 . ?
O2 Co1 N1 97.90(19) 3_666 . ?
O3 Co1 N1 84.13(18) 3_666 . ?
O1 Co1 O2 87.93(16) . . ?
N2 Co1 O2 87.34(18) 3_666 . ?
O2 Co1 O2 82.19(17) 3_666 . ?
O3 Co1 O2 175.86(16) 3_666 . ?
N1 Co1 O2 98.75(18) . . ?
O1 Co1 Co1 128.09(13) . 3_666 ?
N2 Co1 Co1 83.66(14) 3_666 3_666 ?
O2 Co1 Co1 42.03(12) 3_666 3_666 ?
O3 Co1 Co1 136.48(13) 3_666 3_666 ?
N1 Co1 Co1 101.08(15) . 3_666 ?
O2 Co1 Co1 40.16(11) . 3_666 ?
C21 O3 Co1 124.5(3) . 3_666 ?
C19 O2 Co1 108.5(3) . 3_666 ?
C19 O2 Co1 117.6(3) . . ?
Co1 O2 Co1 97.81(17) 3_666 . ?
C17 O1 Co1 107.1(3) . . ?
C6 N2 C10 120.3(5) . . ?
C6 N2 Co1 125.5(4) . 3_666 ?
C10 N2 Co1 114.1(4) . 3_666 ?
C1 N1 C5 119.7(5) . . ?
C1 N1 Co1 126.1(4) . . ?
C5 N1 Co1 113.6(4) . . ?
C11 N3 C15 118.3(6) . . ?
C9 C10 N2 119.9(5) . . ?
C9 C10 C19 128.7(5) . . ?
N2 C10 C19 111.2(5) . . ?
N1 C5 C4 121.3(5) . . ?
N1 C5 C17 109.8(5) . . ?
C4 C5 C17 128.8(5) . . ?
O2 C19 C10 107.8(5) . . ?
O2 C19 C20 107.4(4) . . ?
C10 C19 C20 108.7(5) . . ?
O2 C19 C18 108.0(4) . . ?
C10 C19 C18 116.3(5) . . ?
C20 C19 C18 108.3(5) . . ?
C10 C9 C8 120.4(5) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
N3 C15 C14 121.3(6) . . ?
N3 C15 C21 118.4(5) . . ?
C14 C15 C21 120.1(6) . . ?
N2 C6 C7 121.4(5) . . ?
N2 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
O1 C17 C5 108.0(5) . . ?
O1 C17 C16 108.6(5) . . ?
C5 C17 C16 112.9(5) . . ?
O1 C17 C18 112.1(5) . . ?
C5 C17 C18 107.9(5) . . ?
C16 C17 C18 107.4(5) . . ?
C9 C8 C7 118.8(6) . . ?
C9 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
C13 C14 C15 118.3(6) . . ?
C13 C14 H14 120.9 . . ?
C15 C14 H14 120.9 . . ?
C1 C2 C3 119.4(6) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C6 C7 C8 119.2(5) . . ?
C6 C7 H7 120.4 . . ?
C8 C7 H7 120.4 . . ?
C19 C18 C17 118.2(5) . . ?
C19 C18 H18A 107.8 . . ?
C17 C18 H18A 107.8 . . ?
C19 C18 H18B 107.8 . . ?
C17 C18 H18B 107.8 . . ?
H18A C18 H18B 107.1 . . ?
O3 C21 C22 106.9(5) . . ?
O3 C21 C20 113.3(5) . . ?
C22 C21 C20 107.6(5) . . ?
O3 C21 C15 112.0(5) . . ?
C22 C21 C15 105.8(5) . . ?
C20 C21 C15 110.8(5) . . ?
C19 C20 C21 117.1(5) . . ?
C19 C20 H20A 108.0 . . ?
C21 C20 H20A 108.0 . . ?
C19 C20 H20B 108.0 . . ?
C21 C20 H20B 108.0 . . ?
H20A C20 H20B 107.3 . . ?
N3 C11 C12 123.8(6) . . ?
N3 C11 H11 118.1 . . ?
C12 C11 H11 118.1 . . ?
N1 C1 C2 122.1(6) . . ?
N1 C1 H1 119.0 . . ?
C2 C1 H1 119.0 . . ?
C5 C4 C3 118.3(6) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C11 C12 C13 117.1(6) . . ?
C11 C12 H12 121.4 . . ?
C13 C12 H12 121.4 . . ?
C17 C16 H16A 109.5 . . ?
C17 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C17 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C2 C3 C4 119.1(6) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C14 C13 C12 121.1(7) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?

_refine_diff_density_max         0.626
_refine_diff_density_min         -1.118
_refine_diff_density_rms         0.130



####################################################################### 
# 
# 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_205b1
_database_code_depnum_ccdc_archive 'CCDC 1531809'
_audit_update_record             
;
2017-02-08 deposited with the CCDC.
2017-06-12 downloaded from the CCDC.
;

_vrf_PLAT606_205b1               
;
PROBLEM: VERY LARGE Solvent Accessible VOID(S) in Structure 
RESPONSE: See the "_refine_special_details" and "_platon_squeeze_details"
of the .cif.
;

_vrf_PLAT869_205b1               
;
PROBLEM: ALERTS Related to the use of SQUEEZE Suppressed  
RESPONSE: See the "_refine_special_details" and "_platon_squeeze_details"
of the .cif.
;

_vrf_PLAT058_205b1               
;
PROBLEM: Maximum Transmission Factor Missing ............          ?      
RESPONSE: Original integration and absorption correction files were lost
in a hard drive crash.
;
_vrf_PLAT059_205b1               
;
PROBLEM: Minimum Transmission Factor Missing ............          ?      
RESPONSE: See response to PLAT058.
;
_vrf_PLAT183_205b1               
;
PROBLEM: Missing _cell_measurement_reflns_used value ....     Please Do ! 
RESPONSE: See response to PLAT058.
;
_vrf_PLAT184_205b1               
;
PROBLEM: Missing _cell_measurement_theta_min value ......     Please Do ! 
RESPONSE: See response to PLAT058.
;
_vrf_PLAT185_205b1               
;
PROBLEM: Missing _cell_measurement_theta_max value ......     Please Do ! 
RESPONSE: See response to PLAT058.
;
_vrf_PLAT213_205b1               
;
PROBLEM: Atom F19A            has ADP max/min Ratio .....        4.1 oblate
RESPONSE: A number of CF3 groups were modeled as disordered. Adding additional
parameters for other CF3 groups did not greatly improve the overall refinement
metrics.
;
_vrf_PLAT215_205b1               
;
PROBLEM: Disordered F24A      has ADP max/min Ratio .....        4.4 Note  
RESPONSE: See response to PLAT213.
;
_vrf_PLAT910_205b1               
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min)          28 Note  
RESPONSE:These data were collected with an image plate detector. It is not 
possible to increase the distance from the crystal to the detector, 
which prevented the collection of additional images to overcome
this alert. However this does not present a problem since there are 14876  
independent reflections and a data/parameter ratio of ~12.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H12 B F24, C45 H48 Mn3 N6 O7, H2 O'
_chemical_formula_sum            'C77 H62 B F24 Mn3 N6 O8'
_chemical_formula_weight         1830.95

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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   32.9393(14)
_cell_length_b                   32.2445(14)
_cell_length_c                   15.9331(11)
_cell_angle_alpha                90
_cell_angle_beta                 94.087(7)
_cell_angle_gamma                90
_cell_volume                     16879.7(16)
_cell_formula_units_Z            8
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Block
_exptl_crystal_colour            Red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_F_000             7408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.550
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Mercury275R CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 6.8
_diffrn_reflns_number            92206
_diffrn_reflns_av_unetI/netI     0.0854
_diffrn_reflns_av_R_equivalents  0.1276
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.989
_diffrn_reflns_theta_max         25.025
_diffrn_reflns_theta_full        25.025
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             14876
_reflns_number_gt                11347
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 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. 
;

_computing_data_collection       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
; 
PROBLEM: VERY LARGE Solvent Accessible VOID(S) in Structure 
RESPONSE: See the "_refine_special_details" and "_platon_squeeze_details" 
of the .cif. 
;
_computing_publication_material  'CIFTAB-2013/2 (Sheldrick, 2014)'
_refine_special_details          
; 
Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 

The hydrogen atoms were first found in the difference map, then generated 
geometrically and refined as riding atoms with C-H distances = 0.95 - 0.99 
angstroms and Uiso(H) = 1.2 times Ueq(C) for CH and CH2 groups and Uiso(H) 
= 1.5 times Ueq(C) for CH3 groups.

A number of CF3 groups were modeled as disordered. Adding additional
parameters for other CF3 groups did not greatly improve the overall refinement
metrics.

The program SQUEEZE was used to compensate for the contribution of disordered solvents contained in the voids in the crystal lattice from the diffraction intensities (Acta Cryst. 2009, D65, 148-155). This procedure was applied to the data file and the submitted model is based on the solvent removed data. Based on the total electron density found in the voids (449e/ 2192.5 A3), it is likely that ~11 dichloromethane molecules are present in the unit cell. See platon squeeze details in the .cif for more information.

;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0494P)²+115.5385P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     SHELXT
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         14876
_refine_ls_number_parameters     1195
_refine_ls_number_restraints     148
_refine_ls_R_factor_all          0.1284
_refine_ls_R_factor_gt           0.0951
_refine_ls_wR_factor_ref         0.1843
_refine_ls_wR_factor_gt          0.1716
_refine_ls_goodness_of_fit_ref   1.168
_refine_ls_restrained_S_all      1.175
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.22451(2) 0.55715(3) 0.50901(5) 0.0202(2) Uani 1 1 d . . . . .
Mn2 Mn 0.25825(2) 0.47129(3) 0.51344(5) 0.0195(2) Uani 1 1 d . . . . .
Mn3 Mn 0.16819(2) 0.48533(3) 0.50239(5) 0.0190(2) Uani 1 1 d . . . . .
O1 O 0.24149(11) 0.60421(11) 0.4542(2) 0.0238(9) Uani 1 1 d . . . . .
O2 O 0.26903(11) 0.52167(11) 0.4462(2) 0.0226(9) Uani 1 1 d . . . . .
O3 O 0.28888(10) 0.43130(11) 0.4633(2) 0.0221(9) Uani 1 1 d . . . . .
O4 O 0.20495(10) 0.44874(11) 0.4402(2) 0.0209(9) Uani 1 1 d . . . . .
O5 O 0.11868(11) 0.47754(11) 0.4426(2) 0.0229(9) Uani 1 1 d . . . . .
O6 O 0.17491(11) 0.54239(11) 0.4395(2) 0.0217(9) Uani 1 1 d . . . . .
O7 O 0.21749(10) 0.50442(11) 0.5617(2) 0.0190(8) Uani 1 1 d . . . . .
N1 N 0.26695(13) 0.57805(14) 0.6003(3) 0.0230(11) Uani 1 1 d . . . . .
N2 N 0.31726(13) 0.49733(14) 0.5745(3) 0.0224(11) Uani 1 1 d . . . . .
N3 N 0.25483(13) 0.42494(14) 0.6021(3) 0.0200(10) Uani 1 1 d . . . . .
N4 N 0.16024(13) 0.42041(14) 0.5570(3) 0.0206(10) Uani 1 1 d . . . . .
N5 N 0.12973(13) 0.51096(14) 0.5882(3) 0.0204(10) Uani 1 1 d . . . . .
N6 N 0.17323(13) 0.59646(14) 0.5611(3) 0.0227(11) Uani 1 1 d . . . . .
C1 C 0.27171(17) 0.56726(18) 0.6812(4) 0.0251(13) Uani 1 1 d . . . . .
H1 H 0.2542 0.5468 0.7020 0.030 Uiso 1 1 calc R U . . .
C2 C 0.30133(18) 0.58496(19) 0.7355(4) 0.0301(14) Uani 1 1 d . . . . .
H2 H 0.3042 0.5771 0.7931 0.036 Uiso 1 1 calc R U . . .
C3 C 0.32678(18) 0.6144(2) 0.7041(4) 0.0343(16) Uani 1 1 d . . . . .
H3 H 0.3474 0.6271 0.7402 0.041 Uiso 1 1 calc R U . . .
C4 C 0.32210(17) 0.62531(19) 0.6193(4) 0.0304(15) Uani 1 1 d . . . . .
H4 H 0.3394 0.6454 0.5967 0.036 Uiso 1 1 calc R U . . .
C5 C 0.29175(16) 0.60631(17) 0.5688(4) 0.0204(12) Uani 1 1 d . . . . .
C6 C 0.29075(18) 0.65738(18) 0.4478(4) 0.0349(16) Uani 1 1 d . . . . .
H6A H 0.2844 0.6602 0.3870 0.052 Uiso 1 1 calc R U . . .
H6B H 0.3194 0.6646 0.4615 0.052 Uiso 1 1 calc R U . . .
H6C H 0.2733 0.6760 0.4778 0.052 Uiso 1 1 calc R U . . .
C7 C 0.28339(16) 0.61284(17) 0.4743(4) 0.0226(13) Uani 1 1 d . . . . .
C8 C 0.31011(17) 0.58331(18) 0.4251(4) 0.0260(14) Uani 1 1 d . . . . .
H8A H 0.3022 0.5871 0.3645 0.031 Uiso 1 1 calc R U . . .
H8B H 0.3386 0.5928 0.4347 0.031 Uiso 1 1 calc R U . . .
C9 C 0.30959(15) 0.53637(17) 0.4432(4) 0.0215(13) Uani 1 1 d . . . . .
C10 C 0.32872(17) 0.5138(2) 0.3708(4) 0.0306(14) Uani 1 1 d . . . . .
H10A H 0.3312 0.4842 0.3839 0.046 Uiso 1 1 calc R U . . .
H10B H 0.3558 0.5254 0.3636 0.046 Uiso 1 1 calc R U . . .
H10C H 0.3114 0.5176 0.3187 0.046 Uiso 1 1 calc R U . . .
C11 C 0.33895(18) 0.48353(19) 0.6430(4) 0.0279(14) Uani 1 1 d . . . . .
H11 H 0.3265 0.4642 0.6783 0.034 Uiso 1 1 calc R U . . .
C12 C 0.37843(17) 0.49582(18) 0.6652(4) 0.0291(14) Uani 1 1 d . . . . .
H12 H 0.3927 0.4855 0.7148 0.035 Uiso 1 1 calc R U . . .
C13 C 0.39665(19) 0.5234(2) 0.6136(4) 0.0370(16) Uani 1 1 d . . . . .
H13 H 0.4238 0.5323 0.6268 0.044 Uiso 1 1 calc R U . . .
C14 C 0.37478(17) 0.53777(19) 0.5422(4) 0.0300(14) Uani 1 1 d . . . . .
H14 H 0.3870 0.5565 0.5055 0.036 Uiso 1 1 calc R U . . .
C15 C 0.33499(16) 0.52474(17) 0.5244(3) 0.0211(12) Uani 1 1 d . . . . .
C16 C 0.24390(16) 0.42745(18) 0.6807(4) 0.0241(13) Uani 1 1 d . . . . .
H16 H 0.2371 0.4539 0.7021 0.029 Uiso 1 1 calc R U . . .
C17 C 0.24206(16) 0.39314(18) 0.7327(4) 0.0253(13) Uani 1 1 d . . . . .
H17 H 0.2346 0.3956 0.7890 0.030 Uiso 1 1 calc R U . . .
C18 C 0.25164(17) 0.3549(2) 0.6989(4) 0.0291(14) Uani 1 1 d . . . . .
H18 H 0.2507 0.3306 0.7325 0.035 Uiso 1 1 calc R U . . .
C19 C 0.26252(16) 0.35176(18) 0.6173(4) 0.0257(14) Uani 1 1 d . . . . .
H19 H 0.2688 0.3256 0.5938 0.031 Uiso 1 1 calc R U . . .
C20 C 0.26414(14) 0.38804(17) 0.5698(3) 0.0183(12) Uani 1 1 d . . . . .
C21 C 0.30865(17) 0.36056(19) 0.4597(4) 0.0270(14) Uani 1 1 d . . . . .
H21A H 0.3153 0.3637 0.4011 0.041 Uiso 1 1 calc R U . . .
H21B H 0.2996 0.3321 0.4690 0.041 Uiso 1 1 calc R U . . .
H21C H 0.3329 0.3664 0.4971 0.041 Uiso 1 1 calc R U . . .
C22 C 0.27462(16) 0.39090(17) 0.4784(3) 0.0214(13) Uani 1 1 d . . . . .
C23 C 0.23615(16) 0.38090(17) 0.4201(4) 0.0229(13) Uani 1 1 d . . . . .
H23A H 0.2300 0.3510 0.4263 0.027 Uiso 1 1 calc R U . . .
H23B H 0.2430 0.3853 0.3612 0.027 Uiso 1 1 calc R U . . .
C24 C 0.19666(16) 0.40556(17) 0.4334(3) 0.0212(13) Uani 1 1 d . . . . .
C25 C 0.16709(17) 0.39863(18) 0.3556(3) 0.0243(13) Uani 1 1 d . . . . .
H25A H 0.1418 0.4139 0.3623 0.036 Uiso 1 1 calc R U . . .
H25B H 0.1610 0.3690 0.3496 0.036 Uiso 1 1 calc R U . . .
H25C H 0.1796 0.4086 0.3053 0.036 Uiso 1 1 calc R U . . .
C26 C 0.13677(16) 0.40995(19) 0.6193(4) 0.0250(13) Uani 1 1 d . . . . .
H26 H 0.1265 0.4313 0.6531 0.030 Uiso 1 1 calc R U . . .
C27 C 0.12716(17) 0.36937(18) 0.6356(4) 0.0258(14) Uani 1 1 d . . . . .
H27 H 0.1103 0.3630 0.6797 0.031 Uiso 1 1 calc R U . . .
C28 C 0.14209(17) 0.33823(18) 0.5880(4) 0.0248(13) Uani 1 1 d . . . . .
H28 H 0.1362 0.3100 0.5989 0.030 Uiso 1 1 calc R U . . .
C29 C 0.16608(16) 0.34930(18) 0.5232(4) 0.0252(14) Uani 1 1 d . . . . .
H29 H 0.1766 0.3285 0.4884 0.030 Uiso 1 1 calc R U . . .
C30 C 0.17461(15) 0.39065(17) 0.5093(3) 0.0192(12) Uani 1 1 d . . . . .
C31 C 0.13593(17) 0.51754(17) 0.6709(4) 0.0238(13) Uani 1 1 d . . . . .
H31 H 0.1619 0.5110 0.6976 0.029 Uiso 1 1 calc R U . . .
C32 C 0.10656(18) 0.53333(18) 0.7194(4) 0.0281(14) Uani 1 1 d . . . . .
H32 H 0.1114 0.5367 0.7785 0.034 Uiso 1 1 calc R U . . .
C33 C 0.06923(18) 0.54420(19) 0.6773(4) 0.0315(15) Uani 1 1 d . . . . .
H33 H 0.0484 0.5562 0.7077 0.038 Uiso 1 1 calc R U . . .
C34 C 0.06272(17) 0.53759(18) 0.5924(4) 0.0302(15) Uani 1 1 d . . . . .
H34 H 0.0374 0.5449 0.5640 0.036 Uiso 1 1 calc R U . . .
C35 C 0.09325(15) 0.52022(16) 0.5478(3) 0.0179(12) Uani 1 1 d . . . . .
C36 C 0.04903(16) 0.49474(19) 0.4231(4) 0.0291(14) Uani 1 1 d . . . . .
H36A H 0.0496 0.4865 0.3640 0.044 Uiso 1 1 calc R U . . .
H36B H 0.0290 0.5169 0.4280 0.044 Uiso 1 1 calc R U . . .
H36C H 0.0416 0.4708 0.4567 0.044 Uiso 1 1 calc R U . . .
C37 C 0.09086(15) 0.51029(18) 0.4550(4) 0.0243(13) Uani 1 1 d . . . . .
C38 C 0.10196(17) 0.54827(18) 0.4029(4) 0.0257(14) Uani 1 1 d . . . . .
H38A H 0.0797 0.5688 0.4055 0.031 Uiso 1 1 calc R U . . .
H38B H 0.1023 0.5393 0.3435 0.031 Uiso 1 1 calc R U . . .
C39 C 0.14269(16) 0.57110(17) 0.4266(4) 0.0214(13) Uani 1 1 d . . . . .
C40 C 0.15179(17) 0.59935(19) 0.3523(4) 0.0281(14) Uani 1 1 d . . . . .
H40A H 0.1760 0.6161 0.3677 0.042 Uiso 1 1 calc R U . . .
H40B H 0.1285 0.6177 0.3388 0.042 Uiso 1 1 calc R U . . .
H40C H 0.1567 0.5822 0.3032 0.042 Uiso 1 1 calc R U . . .
C41 C 0.17573(19) 0.62315(19) 0.6248(4) 0.0301(14) Uani 1 1 d . . . . .
H41 H 0.1987 0.6215 0.6643 0.036 Uiso 1 1 calc R U . . .
C42 C 0.14671(19) 0.65322(19) 0.6367(4) 0.0342(15) Uani 1 1 d . . . . .
H42 H 0.1493 0.6714 0.6837 0.041 Uiso 1 1 calc R U . . .
C43 C 0.11398(19) 0.6560(2) 0.5784(4) 0.0348(16) Uani 1 1 d . . . . .
H43 H 0.0936 0.6764 0.5842 0.042 Uiso 1 1 calc R U . . .
C44 C 0.11092(18) 0.62859(18) 0.5109(4) 0.0293(14) Uani 1 1 d . . . . .
H44 H 0.0884 0.6300 0.4703 0.035 Uiso 1 1 calc R U . . .
C45 C 0.14125(16) 0.59921(17) 0.5036(3) 0.0197(12) Uani 1 1 d . . . . .
F1 F 0.39486(13) 0.42614(14) 0.3383(3) 0.0721(15) Uani 1 1 d . . . . .
F2 F 0.43084(19) 0.45596(15) 0.4358(3) 0.0916(19) Uani 1 1 d . . . . .
F3 F 0.44858(14) 0.45723(13) 0.3095(3) 0.0660(13) Uani 1 1 d . . . . .
F4 F 0.30025(12) 0.25522(13) 0.7262(2) 0.0507(11) Uani 1 1 d . . . . .
F5 F 0.29298(10) 0.23978(12) 0.5950(2) 0.0438(10) Uani 1 1 d . . . . .
F6 F 0.33650(11) 0.20744(12) 0.6763(2) 0.0446(10) Uani 1 1 d . . . . .
F7 F 0.54492(11) 0.28289(14) 0.7310(3) 0.0586(12) Uani 1 1 d . . . . .
F8 F 0.56824(14) 0.22137(14) 0.7456(3) 0.0711(15) Uani 1 1 d . . . . .
F9 F 0.58704(11) 0.25992(15) 0.6474(3) 0.0613(13) Uani 1 1 d . . . . .
F10 F 0.28468(12) 0.24582(18) 0.3465(3) 0.0862(18) Uani 1 1 d . . . . .
F11 F 0.29135(12) 0.30235(13) 0.2864(3) 0.0725(15) Uani 1 1 d . . . . .
F12 F 0.28728(14) 0.24551(18) 0.2173(3) 0.0894(18) Uani 1 1 d . . . . .
F13A F 0.4002(4) 0.3643(5) 0.8098(8) 0.064(3) Uani 0.5 1 d . U P A 1
F14A F 0.4265(6) 0.3987(7) 0.7115(11) 0.065(5) Uani 0.5 1 d . U P A 1
F15A F 0.3588(7) 0.3966(10) 0.7266(17) 0.056(5) Uani 0.5 1 d . U P A 1
F16A F 0.5857(3) 0.3591(5) 0.4461(10) 0.064(4) Uani 0.396(17) 1 d . U P B 1
F17A F 0.5740(4) 0.3180(4) 0.3443(17) 0.071(5) Uani 0.396(17) 1 d . U P B 1
F18A F 0.5790(13) 0.3846(11) 0.343(2) 0.057(6) Uani 0.396(17) 1 d . U P B 1
F19A F 0.4599(7) 0.1771(5) 0.2401(11) 0.085(5) Uani 0.3333 1 d . U P C 1
F20A F 0.4168(6) 0.1850(7) 0.1437(15) 0.083(5) Uani 0.3333 1 d . U P C 1
F21A F 0.4594(8) 0.2299(8) 0.1543(19) 0.057(6) Uani 0.3333 1 d . U P C 1
F22A F 0.4833(5) 0.1158(8) 0.4925(14) 0.102(5) Uani 0.5 1 d . U P D 1
F23A F 0.4892(8) 0.1083(10) 0.6216(17) 0.077(5) Uani 0.5 1 d . U P D 1
F24A F 0.4300(4) 0.1270(6) 0.5590(13) 0.072(5) Uani 0.5 1 d . U P D 1
F13B F 0.4212(4) 0.3675(5) 0.7938(10) 0.079(4) Uani 0.5 1 d . U P A 2
F14B F 0.4188(6) 0.4055(7) 0.6836(12) 0.062(4) Uani 0.5 1 d . U P A 2
F15B F 0.3672(6) 0.3977(9) 0.7469(16) 0.051(4) Uani 0.5 1 d . U P A 2
F16B F 0.5845(2) 0.3321(5) 0.4132(9) 0.078(4) Uani 0.604(17) 1 d . U P B 2
F17B F 0.5621(3) 0.3258(3) 0.2838(8) 0.064(3) Uani 0.604(17) 1 d . U P B 2
F18B F 0.5747(8) 0.3845(7) 0.3219(13) 0.050(4) Uani 0.604(17) 1 d . U P B 2
F19B F 0.4377(3) 0.1702(2) 0.2004(6) 0.0538(18) Uani 0.6667 1 d . U P C 2
F20B F 0.4126(3) 0.2105(3) 0.1093(5) 0.067(2) Uani 0.6667 1 d . U P C 2
F21B F 0.4689(4) 0.2274(5) 0.1800(9) 0.070(4) Uani 0.6667 1 d . U P C 2
F22B F 0.4982(5) 0.1147(8) 0.5110(14) 0.097(4) Uani 0.5 1 d D U P D 2
F23B F 0.4799(9) 0.1148(9) 0.6380(18) 0.096(6) Uani 0.5 1 d . U P D 2
F24B F 0.4392(5) 0.1211(7) 0.5265(14) 0.092(6) Uani 0.5 1 d D U P D 2
C47 C 0.40547(16) 0.29656(18) 0.5500(4) 0.0275(14) Uani 1 1 d . . . . .
C48 C 0.41135(19) 0.33150(19) 0.6018(4) 0.0323(15) Uani 1 1 d . . . . .
H48 H 0.4318 0.3509 0.5896 0.039 Uiso 1 1 calc R U . . .
C49 C 0.38848(19) 0.33902(19) 0.6704(4) 0.0355(16) Uani 1 1 d . . . . .
C50 C 0.35890(18) 0.31112(19) 0.6900(4) 0.0330(16) Uani 1 1 d . . . . .
H50 H 0.3433 0.3159 0.7369 0.040 Uiso 1 1 calc R U . . .
C51 C 0.35218(16) 0.27605(19) 0.6406(4) 0.0258(14) Uani 1 1 d . . . . .
C52 C 0.37557(16) 0.26899(18) 0.5739(4) 0.0264(14) Uani 1 1 d . . . . .
H52 H 0.3712 0.2441 0.5425 0.032 Uiso 1 1 calc R U . . .
C53 C 0.32059(19) 0.2454(2) 0.6601(4) 0.0330(15) Uani 1 1 d . . . . .
C54 C 0.3966(3) 0.3756(2) 0.7257(5) 0.0520(17) Uani 1 1 d . U . . .
C55 C 0.45904(17) 0.32348(19) 0.4410(4) 0.0272(14) Uani 1 1 d . . . . .
C56 C 0.49927(17) 0.32221(19) 0.4181(4) 0.0332(16) Uani 1 1 d . . . . .
H56 H 0.5145 0.2975 0.4284 0.040 Uiso 1 1 calc R U . . .
C57 C 0.51788(18) 0.3552(2) 0.3813(5) 0.0382(17) Uani 1 1 d . . . . .
C58 C 0.49666(18) 0.3918(2) 0.3639(4) 0.0389(17) Uani 1 1 d . . . . .
H58 H 0.5094 0.4146 0.3388 0.047 Uiso 1 1 calc R U . . .
C59 C 0.45634(18) 0.3943(2) 0.3840(4) 0.0331(15) Uani 1 1 d . . . . .
C60 C 0.43843(18) 0.36079(19) 0.4209(4) 0.0320(15) Uani 1 1 d . . . . .
H60 H 0.4107 0.3631 0.4335 0.038 Uiso 1 1 calc R U . . .
C61 C 0.4327(2) 0.4334(2) 0.3674(5) 0.0474(19) Uani 1 1 d . . . . .
C62 C 0.5610(2) 0.3511(2) 0.3593(6) 0.0555(19) Uani 1 1 d . U . . .
C63 C 0.40984(17) 0.26505(18) 0.3922(4) 0.0285(14) Uani 1 1 d . . . . .
C64 C 0.42992(19) 0.2439(2) 0.3304(4) 0.0374(17) Uani 1 1 d . . . . .
H64 H 0.4581 0.2382 0.3409 0.045 Uiso 1 1 calc R U . . .
C65 C 0.4105(2) 0.2310(2) 0.2546(5) 0.0390(17) Uani 1 1 d . . . . .
C66 C 0.3696(2) 0.2373(2) 0.2378(4) 0.0372(16) Uani 1 1 d . . . . .
H66 H 0.3560 0.2276 0.1869 0.045 Uiso 1 1 calc R U . . .
C67 C 0.34864(18) 0.25806(19) 0.2973(4) 0.0308(15) Uani 1 1 d . . . . .
C68 C 0.36866(17) 0.27218(18) 0.3711(4) 0.0269(14) Uani 1 1 d . . . . .
H68 H 0.3536 0.2875 0.4092 0.032 Uiso 1 1 calc R U . . .
C69 C 0.3041(2) 0.2643(2) 0.2826(5) 0.0423(18) Uani 1 1 d . . . . .
C70 C 0.4340(2) 0.2089(2) 0.1925(5) 0.0520(18) Uani 1 1 d . U . . .
C71 C 0.46564(17) 0.24944(19) 0.5236(4) 0.0329(15) Uani 1 1 d . . . . .
C72 C 0.45866(18) 0.2069(2) 0.5199(5) 0.0397(18) Uani 1 1 d . . . . .
H72 H 0.4377 0.1969 0.4812 0.048 Uiso 1 1 calc R U . . .
C73 C 0.48064(18) 0.17824(19) 0.5696(5) 0.0403(18) Uani 1 1 d . . . . .
C74 C 0.51212(18) 0.1918(2) 0.6255(5) 0.0408(18) Uani 1 1 d . . . . .
H74 H 0.5275 0.1725 0.6597 0.049 Uiso 1 1 calc R U . . .
C75 C 0.52075(17) 0.2337(2) 0.6308(4) 0.0339(16) Uani 1 1 d . . . . .
C76 C 0.49744(16) 0.26149(19) 0.5809(4) 0.0331(16) Uani 1 1 d . . . . .
H76 H 0.5035 0.2902 0.5863 0.040 Uiso 1 1 calc R U . . .
C77 C 0.5550(2) 0.2493(2) 0.6882(5) 0.0425(18) Uani 1 1 d . . . . .
C78 C 0.4715(3) 0.1337(2) 0.5664(8) 0.078(2) Uani 1 1 d . U . . .
B1 B 0.4350(2) 0.2834(2) 0.4763(5) 0.0323(18) Uani 1 1 d . . . . .
O8 O 0.22083(15) 0.49490(15) 0.2958(3) 0.0379(11) Uani 1 1 d D . . . .
H8C H 0.211(2) 0.4759(16) 0.325(3) 0.06(3) Uiso 1 1 d D . . . .
H8D H 0.234(2) 0.5118(16) 0.328(3) 0.06(3) Uiso 1 1 d D . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mn1 O1 1.857(4) . ?
Mn1 O7 1.918(4) . ?
Mn1 O6 1.965(4) . ?
Mn1 N1 2.058(5) . ?
Mn1 O2 2.161(4) . ?
Mn1 N6 2.313(5) . ?
Mn1 Mn3 2.9644(12) . ?
Mn1 Mn2 2.9822(12) . ?
Mn2 O3 1.853(4) . ?
Mn2 O7 1.919(4) . ?
Mn2 O2 1.992(4) . ?
Mn2 N3 2.065(5) . ?
Mn2 O4 2.163(4) . ?
Mn2 N2 2.272(5) . ?
Mn2 Mn3 2.9934(11) . ?
Mn3 O5 1.847(4) . ?
Mn3 O7 1.921(3) . ?
Mn3 O4 2.002(4) . ?
Mn3 N5 2.098(4) . ?
Mn3 O6 2.114(4) . ?
Mn3 N4 2.289(5) . ?
O1 C7 1.422(6) . ?
O2 C9 1.422(6) . ?
O3 C22 1.411(7) . ?
O4 C24 1.422(6) . ?
O5 C37 1.421(6) . ?
O6 C39 1.412(6) . ?
N1 C1 1.333(7) . ?
N1 C5 1.344(7) . ?
N2 C11 1.337(7) . ?
N2 C15 1.351(7) . ?
N3 C16 1.331(7) . ?
N3 C20 1.340(7) . ?
N4 C30 1.331(7) . ?
N4 C26 1.344(7) . ?
N5 C31 1.336(7) . ?
N5 C35 1.355(6) . ?
N6 C41 1.329(7) . ?
N6 C45 1.349(7) . ?
C1 C2 1.381(8) . ?
C1 H1 0.9500 . ?
C2 C3 1.383(9) . ?
C2 H2 0.9500 . ?
C3 C4 1.395(9) . ?
C3 H3 0.9500 . ?
C4 C5 1.381(8) . ?
C4 H4 0.9500 . ?
C5 C7 1.526(8) . ?
C6 C7 1.521(8) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.547(8) . ?
C8 C9 1.541(8) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.535(8) . ?
C9 C15 1.537(8) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.381(8) . ?
C11 H11 0.9500 . ?
C12 C13 1.377(9) . ?
C12 H12 0.9500 . ?
C13 C14 1.382(9) . ?
C13 H13 0.9500 . ?
C14 C15 1.386(8) . ?
C14 H14 0.9500 . ?
C16 C17 1.386(8) . ?
C16 H16 0.9500 . ?
C17 C18 1.392(8) . ?
C17 H17 0.9500 . ?
C18 C19 1.377(8) . ?
C18 H18 0.9500 . ?
C19 C20 1.396(8) . ?
C19 H19 0.9500 . ?
C20 C22 1.524(8) . ?
C21 C22 1.533(7) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.551(7) . ?
C23 C24 1.552(7) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C30 1.533(8) . ?
C24 C25 1.537(7) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 C27 1.376(8) . ?
C26 H26 0.9500 . ?
C27 C28 1.371(8) . ?
C27 H27 0.9500 . ?
C28 C29 1.391(8) . ?
C28 H28 0.9500 . ?
C29 C30 1.383(8) . ?
C29 H29 0.9500 . ?
C31 C32 1.378(8) . ?
C31 H31 0.9500 . ?
C32 C33 1.403(8) . ?
C32 H32 0.9500 . ?
C33 C34 1.371(9) . ?
C33 H33 0.9500 . ?
C34 C35 1.389(8) . ?
C34 H34 0.9500 . ?
C35 C37 1.510(8) . ?
C36 C37 1.519(7) . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C37 C38 1.538(8) . ?
C38 C39 1.553(8) . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C39 C45 1.529(8) . ?
C39 C40 1.540(8) . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
C41 C42 1.384(9) . ?
C41 H41 0.9500 . ?
C42 C43 1.375(9) . ?
C42 H42 0.9500 . ?
C43 C44 1.389(9) . ?
C43 H43 0.9500 . ?
C44 C45 1.387(8) . ?
C44 H44 0.9500 . ?
F1 C61 1.319(8) . ?
F2 C61 1.317(9) . ?
F3 C61 1.336(9) . ?
F4 C53 1.327(7) . ?
F5 C53 1.342(7) . ?
F6 C53 1.348(7) . ?
F7 C77 1.336(8) . ?
F8 C77 1.335(8) . ?
F9 C77 1.323(8) . ?
F10 C69 1.375(8) . ?
F11 C69 1.298(8) . ?
F12 C69 1.294(8) . ?
F13A C54 1.386(14) . ?
F14A C54 1.27(2) . ?
F15A C54 1.42(2) . ?
F16A C62 1.575(18) . ?
F17A C62 1.181(14) . ?
F18A C62 1.27(3) . ?
F19A C70 1.50(2) . ?
F20A C70 1.209(18) . ?
F21A C70 1.27(3) . ?
F22A C78 1.39(2) . ?
F23A C78 1.31(3) . ?
F24A C78 1.381(16) . ?
F13B C54 1.332(15) . ?
F14B C54 1.409(19) . ?
F15B C54 1.27(3) . ?
F16B C62 1.271(12) . ?
F17B C62 1.457(13) . ?
F18B C62 1.33(2) . ?
F19B C70 1.261(10) . ?
F20B C70 1.457(11) . ?
F21B C70 1.324(14) . ?
F22B C78 1.43(2) . ?
F23B C78 1.31(3) . ?
F24B C78 1.27(2) . ?
C47 C52 1.400(8) . ?
C47 C48 1.402(8) . ?
C47 B1 1.635(9) . ?
C48 C49 1.392(9) . ?
C48 H48 0.9500 . ?
C49 C50 1.378(9) . ?
C49 C54 1.486(9) . ?
C50 C51 1.387(8) . ?
C50 H50 0.9500 . ?
C51 C52 1.375(8) . ?
C51 C53 1.485(9) . ?
C52 H52 0.9500 . ?
C55 C56 1.400(8) . ?
C55 C60 1.407(8) . ?
C55 B1 1.635(9) . ?
C56 C57 1.380(9) . ?
C56 H56 0.9500 . ?
C57 C58 1.389(9) . ?
C57 C62 1.492(9) . ?
C58 C59 1.391(9) . ?
C58 H58 0.9500 . ?
C59 C60 1.382(9) . ?
C59 C61 1.495(9) . ?
C60 H60 0.9500 . ?
C63 C68 1.393(8) . ?
C63 C64 1.401(8) . ?
C63 B1 1.636(10) . ?
C64 C65 1.389(9) . ?
C64 H64 0.9500 . ?
C65 C66 1.371(9) . ?
C65 C70 1.481(9) . ?
C66 C67 1.385(9) . ?
C66 H66 0.9500 . ?
C67 C68 1.384(8) . ?
C67 C69 1.484(9) . ?
C68 H68 0.9500 . ?
C71 C72 1.391(9) . ?
C71 C76 1.395(8) . ?
C71 B1 1.636(9) . ?
C72 C73 1.387(9) . ?
C72 H72 0.9500 . ?
C73 C74 1.388(9) . ?
C73 C78 1.467(10) . ?
C74 C75 1.383(9) . ?
C74 H74 0.9500 . ?
C75 C76 1.392(9) . ?
C75 C77 1.487(9) . ?
C76 H76 0.9500 . ?
O8 H8C 0.85(2) . ?
O8 H8D 0.85(2) . ?

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 O7 168.61(16) . . ?
O1 Mn1 O6 101.50(16) . . ?
O7 Mn1 O6 84.86(15) . . ?
O1 Mn1 N1 81.53(18) . . ?
O7 Mn1 N1 94.46(17) . . ?
O6 Mn1 N1 166.64(17) . . ?
O1 Mn1 O2 88.72(15) . . ?
O7 Mn1 O2 80.81(15) . . ?
O6 Mn1 O2 100.10(15) . . ?
N1 Mn1 O2 92.94(16) . . ?
O1 Mn1 N6 88.47(16) . . ?
O7 Mn1 N6 102.40(16) . . ?
O6 Mn1 N6 74.68(16) . . ?
N1 Mn1 N6 92.50(17) . . ?
O2 Mn1 N6 173.44(15) . . ?
O1 Mn1 Mn3 146.14(12) . . ?
O7 Mn1 Mn3 39.48(10) . . ?
O6 Mn1 Mn3 45.40(11) . . ?
N1 Mn1 Mn3 132.28(14) . . ?
O2 Mn1 Mn3 90.77(10) . . ?
N6 Mn1 Mn3 88.26(12) . . ?
O1 Mn1 Mn2 130.20(12) . . ?
O7 Mn1 Mn2 39.00(11) . . ?
O6 Mn1 Mn2 94.70(11) . . ?
N1 Mn1 Mn2 93.09(13) . . ?
O2 Mn1 Mn2 41.88(10) . . ?
N6 Mn1 Mn2 141.33(12) . . ?
Mn3 Mn1 Mn2 60.45(3) . . ?
O3 Mn2 O7 167.99(16) . . ?
O3 Mn2 O2 102.28(16) . . ?
O7 Mn2 O2 85.31(15) . . ?
O3 Mn2 N3 81.29(17) . . ?
O7 Mn2 N3 93.15(16) . . ?
O2 Mn2 N3 168.17(17) . . ?
O3 Mn2 O4 88.84(15) . . ?
O7 Mn2 O4 80.74(14) . . ?
O2 Mn2 O4 98.81(14) . . ?
N3 Mn2 O4 92.50(16) . . ?
O3 Mn2 N2 88.06(16) . . ?
O7 Mn2 N2 102.97(16) . . ?
O2 Mn2 N2 75.46(16) . . ?
N3 Mn2 N2 93.51(17) . . ?
O4 Mn2 N2 172.74(16) . . ?
O3 Mn2 Mn1 148.15(12) . . ?
O7 Mn2 Mn1 38.97(11) . . ?
O2 Mn2 Mn1 46.41(11) . . ?
N3 Mn2 Mn1 130.53(13) . . ?
O4 Mn2 Mn1 90.72(10) . . ?
N2 Mn2 Mn1 88.46(12) . . ?
O3 Mn2 Mn3 130.36(12) . . ?
O7 Mn2 Mn3 38.80(10) . . ?
O2 Mn2 Mn3 93.38(11) . . ?
N3 Mn2 Mn3 92.73(12) . . ?
O4 Mn2 Mn3 41.96(10) . . ?
N2 Mn2 Mn3 141.57(12) . . ?
Mn1 Mn2 Mn3 59.48(3) . . ?
O5 Mn3 O7 169.13(16) . . ?
O5 Mn3 O4 101.98(15) . . ?
O7 Mn3 O4 84.98(15) . . ?
O5 Mn3 N5 80.66(17) . . ?
O7 Mn3 N5 94.69(16) . . ?
O4 Mn3 N5 165.62(17) . . ?
O5 Mn3 O6 89.56(15) . . ?
O7 Mn3 O6 80.84(14) . . ?
O4 Mn3 O6 101.02(15) . . ?
N5 Mn3 O6 93.10(16) . . ?
O5 Mn3 N4 87.18(16) . . ?
O7 Mn3 N4 102.82(15) . . ?
O4 Mn3 N4 74.85(16) . . ?
N5 Mn3 N4 91.26(17) . . ?
O6 Mn3 N4 174.06(16) . . ?
O5 Mn3 Mn1 130.70(12) . . ?
O7 Mn3 Mn1 39.41(11) . . ?
O4 Mn3 Mn1 94.53(11) . . ?
N5 Mn3 Mn1 94.27(12) . . ?
O6 Mn3 Mn1 41.45(10) . . ?
N4 Mn3 Mn1 142.12(11) . . ?
O5 Mn3 Mn2 147.66(12) . . ?
O7 Mn3 Mn2 38.76(11) . . ?
O4 Mn3 Mn2 46.25(10) . . ?
N5 Mn3 Mn2 131.53(12) . . ?
O6 Mn3 Mn2 91.30(10) . . ?
N4 Mn3 Mn2 88.81(11) . . ?
Mn1 Mn3 Mn2 60.07(3) . . ?
C7 O1 Mn1 112.0(3) . . ?
C9 O2 Mn2 119.6(3) . . ?
C9 O2 Mn1 120.7(3) . . ?
Mn2 O2 Mn1 91.72(15) . . ?
C22 O3 Mn2 111.8(3) . . ?
C24 O4 Mn3 119.7(3) . . ?
C24 O4 Mn2 121.0(3) . . ?
Mn3 O4 Mn2 91.80(15) . . ?
C37 O5 Mn3 112.4(3) . . ?
C39 O6 Mn1 120.6(3) . . ?
C39 O6 Mn3 122.4(3) . . ?
Mn1 O6 Mn3 93.15(15) . . ?
Mn1 O7 Mn2 102.02(17) . . ?
Mn1 O7 Mn3 101.11(16) . . ?
Mn2 O7 Mn3 102.44(17) . . ?
C1 N1 C5 120.3(5) . . ?
C1 N1 Mn1 128.7(4) . . ?
C5 N1 Mn1 111.0(4) . . ?
C11 N2 C15 118.1(5) . . ?
C11 N2 Mn2 128.1(4) . . ?
C15 N2 Mn2 112.4(3) . . ?
C16 N3 C20 120.0(5) . . ?
C16 N3 Mn2 129.2(4) . . ?
C20 N3 Mn2 110.8(4) . . ?
C30 N4 C26 119.1(5) . . ?
C30 N4 Mn3 112.8(4) . . ?
C26 N4 Mn3 126.7(4) . . ?
C31 N5 C35 120.0(5) . . ?
C31 N5 Mn3 130.4(4) . . ?
C35 N5 Mn3 109.5(3) . . ?
C41 N6 C45 118.6(5) . . ?
C41 N6 Mn1 128.5(4) . . ?
C45 N6 Mn1 110.3(4) . . ?
N1 C1 C2 121.8(6) . . ?
N1 C1 H1 119.1 . . ?
C2 C1 H1 119.1 . . ?
C1 C2 C3 118.4(6) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 H2 120.8 . . ?
C2 C3 C4 119.8(6) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 118.5(6) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
N1 C5 C4 121.2(5) . . ?
N1 C5 C7 113.0(5) . . ?
C4 C5 C7 125.8(5) . . ?
C7 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C7 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O1 C7 C6 107.1(4) . . ?
O1 C7 C5 107.4(4) . . ?
C6 C7 C5 112.5(5) . . ?
O1 C7 C8 110.1(4) . . ?
C6 C7 C8 109.4(5) . . ?
C5 C7 C8 110.2(4) . . ?
C9 C8 C7 119.7(5) . . ?
C9 C8 H8A 107.4 . . ?
C7 C8 H8A 107.4 . . ?
C9 C8 H8B 107.4 . . ?
C7 C8 H8B 107.4 . . ?
H8A C8 H8B 106.9 . . ?
O2 C9 C10 107.8(4) . . ?
O2 C9 C15 110.3(4) . . ?
C10 C9 C15 106.8(4) . . ?
O2 C9 C8 110.9(4) . . ?
C10 C9 C8 108.3(5) . . ?
C15 C9 C8 112.6(5) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C11 C12 123.5(6) . . ?
N2 C11 H11 118.3 . . ?
C12 C11 H11 118.3 . . ?
C13 C12 C11 118.4(6) . . ?
C13 C12 H12 120.8 . . ?
C11 C12 H12 120.8 . . ?
C12 C13 C14 118.9(6) . . ?
C12 C13 H13 120.5 . . ?
C14 C13 H13 120.5 . . ?
C13 C14 C15 119.8(6) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
N2 C15 C14 121.3(5) . . ?
N2 C15 C9 115.1(4) . . ?
C14 C15 C9 123.3(5) . . ?
N3 C16 C17 122.7(5) . . ?
N3 C16 H16 118.6 . . ?
C17 C16 H16 118.6 . . ?
C16 C17 C18 117.1(6) . . ?
C16 C17 H17 121.4 . . ?
C18 C17 H17 121.4 . . ?
C19 C18 C17 120.7(6) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C18 C19 C20 118.2(5) . . ?
C18 C19 H19 120.9 . . ?
C20 C19 H19 120.9 . . ?
N3 C20 C19 121.2(5) . . ?
N3 C20 C22 112.7(5) . . ?
C19 C20 C22 126.0(5) . . ?
C22 C21 H21A 109.5 . . ?
C22 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C22 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O3 C22 C20 108.6(4) . . ?
O3 C22 C21 107.4(4) . . ?
C20 C22 C21 111.4(4) . . ?
O3 C22 C23 111.0(4) . . ?
C20 C22 C23 109.2(4) . . ?
C21 C22 C23 109.2(4) . . ?
C22 C23 C24 118.0(4) . . ?
C22 C23 H23A 107.8 . . ?
C24 C23 H23A 107.8 . . ?
C22 C23 H23B 107.8 . . ?
C24 C23 H23B 107.8 . . ?
H23A C23 H23B 107.2 . . ?
O4 C24 C30 110.2(4) . . ?
O4 C24 C25 108.2(4) . . ?
C30 C24 C25 106.4(4) . . ?
O4 C24 C23 110.7(4) . . ?
C30 C24 C23 113.3(5) . . ?
C25 C24 C23 107.7(4) . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N4 C26 C27 122.1(5) . . ?
N4 C26 H26 119.0 . . ?
C27 C26 H26 119.0 . . ?
C28 C27 C26 119.7(5) . . ?
C28 C27 H27 120.2 . . ?
C26 C27 H27 120.2 . . ?
C27 C28 C29 117.9(5) . . ?
C27 C28 H28 121.0 . . ?
C29 C28 H28 121.0 . . ?
C30 C29 C28 119.9(6) . . ?
C30 C29 H29 120.1 . . ?
C28 C29 H29 120.1 . . ?
N4 C30 C29 121.3(5) . . ?
N4 C30 C24 115.6(5) . . ?
C29 C30 C24 122.8(5) . . ?
N5 C31 C32 123.2(5) . . ?
N5 C31 H31 118.4 . . ?
C32 C31 H31 118.4 . . ?
C31 C32 C33 116.8(6) . . ?
C31 C32 H32 121.6 . . ?
C33 C32 H32 121.6 . . ?
C34 C33 C32 120.2(6) . . ?
C34 C33 H33 119.9 . . ?
C32 C33 H33 119.9 . . ?
C33 C34 C35 119.9(5) . . ?
C33 C34 H34 120.1 . . ?
C35 C34 H34 120.1 . . ?
N5 C35 C34 119.8(5) . . ?
N5 C35 C37 113.6(4) . . ?
C34 C35 C37 126.6(5) . . ?
C37 C36 H36A 109.5 . . ?
C37 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C37 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
O5 C37 C35 107.8(4) . . ?
O5 C37 C36 106.6(4) . . ?
C35 C37 C36 112.3(5) . . ?
O5 C37 C38 109.6(4) . . ?
C35 C37 C38 111.2(5) . . ?
C36 C37 C38 109.1(5) . . ?
C37 C38 C39 118.7(5) . . ?
C37 C38 H38A 107.6 . . ?
C39 C38 H38A 107.6 . . ?
C37 C38 H38B 107.6 . . ?
C39 C38 H38B 107.6 . . ?
H38A C38 H38B 107.1 . . ?
O6 C39 C45 109.7(4) . . ?
O6 C39 C40 108.3(4) . . ?
C45 C39 C40 106.5(4) . . ?
O6 C39 C38 110.6(4) . . ?
C45 C39 C38 113.6(4) . . ?
C40 C39 C38 107.8(4) . . ?
C39 C40 H40A 109.5 . . ?
C39 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C39 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
N6 C41 C42 123.5(6) . . ?
N6 C41 H41 118.2 . . ?
C42 C41 H41 118.2 . . ?
C43 C42 C41 117.9(6) . . ?
C43 C42 H42 121.1 . . ?
C41 C42 H42 121.1 . . ?
C42 C43 C44 119.5(6) . . ?
C42 C43 H43 120.2 . . ?
C44 C43 H43 120.2 . . ?
C45 C44 C43 119.0(6) . . ?
C45 C44 H44 120.5 . . ?
C43 C44 H44 120.5 . . ?
N6 C45 C44 121.4(5) . . ?
N6 C45 C39 116.0(5) . . ?
C44 C45 C39 122.4(5) . . ?
C52 C47 C48 114.9(6) . . ?
C52 C47 B1 119.8(5) . . ?
C48 C47 B1 124.6(5) . . ?
C49 C48 C47 122.9(6) . . ?
C49 C48 H48 118.6 . . ?
C47 C48 H48 118.6 . . ?
C50 C49 C48 119.7(6) . . ?
C50 C49 C54 119.0(6) . . ?
C48 C49 C54 121.3(7) . . ?
C49 C50 C51 119.4(6) . . ?
C49 C50 H50 120.3 . . ?
C51 C50 H50 120.3 . . ?
C52 C51 C50 119.9(6) . . ?
C52 C51 C53 119.4(6) . . ?
C50 C51 C53 120.7(6) . . ?
C51 C52 C47 123.3(6) . . ?
C51 C52 H52 118.4 . . ?
C47 C52 H52 118.4 . . ?
F4 C53 F5 107.1(5) . . ?
F4 C53 F6 106.1(5) . . ?
F5 C53 F6 105.0(5) . . ?
F4 C53 C51 114.1(5) . . ?
F5 C53 C51 111.9(5) . . ?
F6 C53 C51 112.1(5) . . ?
F15B C54 F13B 109.0(14) . . ?
F14A C54 F13A 108.3(11) . . ?
F15B C54 F14B 100.1(18) . . ?
F13B C54 F14B 102.5(12) . . ?
F14A C54 F15A 114.6(18) . . ?
F13A C54 F15A 97.5(14) . . ?
F15B C54 C49 119.7(13) . . ?
F14A C54 C49 118.0(13) . . ?
F13B C54 C49 113.5(9) . . ?
F13A C54 C49 111.3(9) . . ?
F14B C54 C49 109.8(11) . . ?
F15A C54 C49 105.2(13) . . ?
C56 C55 C60 114.6(6) . . ?
C56 C55 B1 123.8(5) . . ?
C60 C55 B1 121.1(5) . . ?
C57 C56 C55 123.1(6) . . ?
C57 C56 H56 118.5 . . ?
C55 C56 H56 118.5 . . ?
C56 C57 C58 120.5(6) . . ?
C56 C57 C62 119.3(6) . . ?
C58 C57 C62 120.2(6) . . ?
C57 C58 C59 118.5(6) . . ?
C57 C58 H58 120.7 . . ?
C59 C58 H58 120.7 . . ?
C60 C59 C58 119.8(6) . . ?
C60 C59 C61 120.1(6) . . ?
C58 C59 C61 120.1(6) . . ?
C59 C60 C55 123.4(6) . . ?
C59 C60 H60 118.3 . . ?
C55 C60 H60 118.3 . . ?
F2 C61 F1 106.8(7) . . ?
F2 C61 F3 107.2(6) . . ?
F1 C61 F3 105.5(6) . . ?
F2 C61 C59 112.0(6) . . ?
F1 C61 C59 112.4(6) . . ?
F3 C61 C59 112.5(6) . . ?
F17A C62 F18A 123(2) . . ?
F16B C62 F18B 119.1(13) . . ?
F16B C62 F17B 103.8(9) . . ?
F18B C62 F17B 93.0(13) . . ?
F17A C62 C57 119.6(8) . . ?
F18A C62 C57 116(2) . . ?
F16B C62 C57 115.4(8) . . ?
F18B C62 C57 113.0(14) . . ?
F17B C62 C57 109.0(7) . . ?
F17A C62 F16A 98.9(13) . . ?
F18A C62 F16A 79.8(17) . . ?
C57 C62 F16A 102.8(8) . . ?
C68 C63 C64 114.3(6) . . ?
C68 C63 B1 124.5(5) . . ?
C64 C63 B1 120.9(5) . . ?
C65 C64 C63 123.1(6) . . ?
C65 C64 H64 118.5 . . ?
C63 C64 H64 118.5 . . ?
C66 C65 C64 120.7(6) . . ?
C66 C65 C70 119.5(7) . . ?
C64 C65 C70 119.7(7) . . ?
C65 C66 C67 118.0(6) . . ?
C65 C66 H66 121.0 . . ?
C67 C66 H66 121.0 . . ?
C68 C67 C66 120.7(6) . . ?
C68 C67 C69 119.7(6) . . ?
C66 C67 C69 119.6(6) . . ?
C67 C68 C63 123.2(6) . . ?
C67 C68 H68 118.4 . . ?
C63 C68 H68 118.4 . . ?
F12 C69 F11 111.1(6) . . ?
F12 C69 F10 101.4(6) . . ?
F11 C69 F10 101.9(6) . . ?
F12 C69 C67 115.1(6) . . ?
F11 C69 C67 116.1(6) . . ?
F10 C69 C67 109.3(6) . . ?
F20A C70 F21A 109.2(17) . . ?
F19B C70 F21B 112.5(10) . . ?
F19B C70 F20B 99.4(7) . . ?
F21B C70 F20B 102.6(9) . . ?
F20A C70 C65 119.7(10) . . ?
F19B C70 C65 117.4(7) . . ?
F21A C70 C65 117.3(15) . . ?
F21B C70 C65 112.6(9) . . ?
F20B C70 C65 110.5(7) . . ?
F20A C70 F19A 96.5(16) . . ?
F21A C70 F19A 103.6(16) . . ?
C65 C70 F19A 107.1(9) . . ?
C72 C71 C76 114.6(6) . . ?
C72 C71 B1 123.1(5) . . ?
C76 C71 B1 121.6(6) . . ?
C73 C72 C71 123.7(6) . . ?
C73 C72 H72 118.1 . . ?
C71 C72 H72 118.1 . . ?
C72 C73 C74 119.5(6) . . ?
C72 C73 C78 122.3(6) . . ?
C74 C73 C78 118.2(6) . . ?
C75 C74 C73 119.1(6) . . ?
C75 C74 H74 120.4 . . ?
C73 C74 H74 120.4 . . ?
C74 C75 C76 119.5(6) . . ?
C74 C75 C77 120.7(6) . . ?
C76 C75 C77 119.8(6) . . ?
C75 C76 C71 123.5(6) . . ?
C75 C76 H76 118.2 . . ?
C71 C76 H76 118.2 . . ?
F9 C77 F8 106.2(6) . . ?
F9 C77 F7 106.0(5) . . ?
F8 C77 F7 106.1(6) . . ?
F9 C77 C75 112.5(6) . . ?
F8 C77 C75 113.0(6) . . ?
F7 C77 C75 112.5(5) . . ?
F24B C78 F23B 114(2) . . ?
F23A C78 F24A 110.5(19) . . ?
F23A C78 F22A 99.8(15) . . ?
F24A C78 F22A 101.3(13) . . ?
F24B C78 F22B 94.8(12) . . ?
F23B C78 F22B 103.7(15) . . ?
F24B C78 C73 119.6(12) . . ?
F23B C78 C73 113.3(17) . . ?
F23A C78 C73 120.6(17) . . ?
F24A C78 C73 110.8(10) . . ?
F22A C78 C73 111.6(14) . . ?
F22B C78 C73 108.0(13) . . ?
C47 B1 C55 111.7(5) . . ?
C47 B1 C71 102.8(5) . . ?
C55 B1 C71 113.0(5) . . ?
C47 B1 C63 112.9(5) . . ?
C55 B1 C63 103.5(5) . . ?
C71 B1 C63 113.3(5) . . ?
H8C O8 H8D 109(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O7 Mn1 O1 C7 -36.9(10) . . . . ?
O6 Mn1 O1 C7 -160.1(3) . . . . ?
N1 Mn1 O1 C7 33.2(3) . . . . ?
O2 Mn1 O1 C7 -60.0(3) . . . . ?
N6 Mn1 O1 C7 125.9(3) . . . . ?
Mn3 Mn1 O1 C7 -149.5(3) . . . . ?
Mn2 Mn1 O1 C7 -53.7(4) . . . . ?
O7 Mn2 O3 C22 -29.4(10) . . . . ?
O2 Mn2 O3 C22 -157.7(3) . . . . ?
N3 Mn2 O3 C22 33.7(3) . . . . ?
O4 Mn2 O3 C22 -59.0(3) . . . . ?
N2 Mn2 O3 C22 127.6(3) . . . . ?
Mn1 Mn2 O3 C22 -148.5(3) . . . . ?
Mn3 Mn2 O3 C22 -52.4(4) . . . . ?
O7 Mn3 O5 C37 -30.3(11) . . . . ?
O4 Mn3 O5 C37 -159.3(3) . . . . ?
N5 Mn3 O5 C37 35.0(4) . . . . ?
O6 Mn3 O5 C37 -58.2(4) . . . . ?
N4 Mn3 O5 C37 126.8(4) . . . . ?
Mn1 Mn3 O5 C37 -52.5(4) . . . . ?
Mn2 Mn3 O5 C37 -149.9(3) . . . . ?
C5 N1 C1 C2 1.3(8) . . . . ?
Mn1 N1 C1 C2 -178.4(4) . . . . ?
N1 C1 C2 C3 -0.6(8) . . . . ?
C1 C2 C3 C4 -0.1(9) . . . . ?
C2 C3 C4 C5 0.2(9) . . . . ?
C1 N1 C5 C4 -1.2(8) . . . . ?
Mn1 N1 C5 C4 178.6(4) . . . . ?
C1 N1 C5 C7 176.6(5) . . . . ?
Mn1 N1 C5 C7 -3.7(5) . . . . ?
C3 C4 C5 N1 0.4(8) . . . . ?
C3 C4 C5 C7 -177.1(5) . . . . ?
Mn1 O1 C7 C6 -163.8(4) . . . . ?
Mn1 O1 C7 C5 -42.7(5) . . . . ?
Mn1 O1 C7 C8 77.3(5) . . . . ?
N1 C5 C7 O1 28.6(6) . . . . ?
C4 C5 C7 O1 -153.7(5) . . . . ?
N1 C5 C7 C6 146.2(5) . . . . ?
C4 C5 C7 C6 -36.1(8) . . . . ?
N1 C5 C7 C8 -91.3(5) . . . . ?
C4 C5 C7 C8 86.3(7) . . . . ?
O1 C7 C8 C9 -65.0(6) . . . . ?
C6 C7 C8 C9 177.5(5) . . . . ?
C5 C7 C8 C9 53.3(6) . . . . ?
Mn2 O2 C9 C10 87.6(5) . . . . ?
Mn1 O2 C9 C10 -160.2(3) . . . . ?
Mn2 O2 C9 C15 -28.6(5) . . . . ?
Mn1 O2 C9 C15 83.5(5) . . . . ?
Mn2 O2 C9 C8 -154.0(3) . . . . ?
Mn1 O2 C9 C8 -41.9(5) . . . . ?
C7 C8 C9 O2 46.4(7) . . . . ?
C7 C8 C9 C10 164.5(5) . . . . ?
C7 C8 C9 C15 -77.6(6) . . . . ?
C15 N2 C11 C12 0.0(8) . . . . ?
Mn2 N2 C11 C12 165.9(4) . . . . ?
N2 C11 C12 C13 -0.8(9) . . . . ?
C11 C12 C13 C14 0.4(9) . . . . ?
C12 C13 C14 C15 0.8(9) . . . . ?
C11 N2 C15 C14 1.2(8) . . . . ?
Mn2 N2 C15 C14 -166.9(4) . . . . ?
C11 N2 C15 C9 175.1(5) . . . . ?
Mn2 N2 C15 C9 7.0(6) . . . . ?
C13 C14 C15 N2 -1.6(9) . . . . ?
C13 C14 C15 C9 -175.0(5) . . . . ?
O2 C9 C15 N2 11.5(7) . . . . ?
C10 C9 C15 N2 -105.3(5) . . . . ?
C8 C9 C15 N2 135.9(5) . . . . ?
O2 C9 C15 C14 -174.7(5) . . . . ?
C10 C9 C15 C14 68.4(7) . . . . ?
C8 C9 C15 C14 -50.3(7) . . . . ?
C20 N3 C16 C17 0.8(8) . . . . ?
Mn2 N3 C16 C17 178.3(4) . . . . ?
N3 C16 C17 C18 -1.0(8) . . . . ?
C16 C17 C18 C19 0.2(8) . . . . ?
C17 C18 C19 C20 0.8(8) . . . . ?
C16 N3 C20 C19 0.2(7) . . . . ?
Mn2 N3 C20 C19 -177.7(4) . . . . ?
C16 N3 C20 C22 178.2(4) . . . . ?
Mn2 N3 C20 C22 0.3(5) . . . . ?
C18 C19 C20 N3 -0.9(8) . . . . ?
C18 C19 C20 C22 -178.7(5) . . . . ?
Mn2 O3 C22 C20 -41.8(5) . . . . ?
Mn2 O3 C22 C21 -162.5(3) . . . . ?
Mn2 O3 C22 C23 78.2(5) . . . . ?
N3 C20 C22 O3 25.4(6) . . . . ?
C19 C20 C22 O3 -156.7(5) . . . . ?
N3 C20 C22 C21 143.5(5) . . . . ?
C19 C20 C22 C21 -38.6(7) . . . . ?
N3 C20 C22 C23 -95.8(5) . . . . ?
C19 C20 C22 C23 82.1(6) . . . . ?
O3 C22 C23 C24 -66.8(6) . . . . ?
C20 C22 C23 C24 52.9(6) . . . . ?
C21 C22 C23 C24 175.0(5) . . . . ?
Mn3 O4 C24 C30 -28.8(5) . . . . ?
Mn2 O4 C24 C30 83.9(4) . . . . ?
Mn3 O4 C24 C25 87.1(5) . . . . ?
Mn2 O4 C24 C25 -160.2(3) . . . . ?
Mn3 O4 C24 C23 -155.0(3) . . . . ?
Mn2 O4 C24 C23 -42.3(5) . . . . ?
C22 C23 C24 O4 47.3(6) . . . . ?
C22 C23 C24 C30 -77.1(6) . . . . ?
C22 C23 C24 C25 165.4(5) . . . . ?
C30 N4 C26 C27 0.1(8) . . . . ?
Mn3 N4 C26 C27 165.8(4) . . . . ?
N4 C26 C27 C28 0.7(8) . . . . ?
C26 C27 C28 C29 -1.2(8) . . . . ?
C27 C28 C29 C30 0.9(8) . . . . ?
C26 N4 C30 C29 -0.4(7) . . . . ?
Mn3 N4 C30 C29 -168.0(4) . . . . ?
C26 N4 C30 C24 172.9(4) . . . . ?
Mn3 N4 C30 C24 5.3(5) . . . . ?
C28 C29 C30 N4 -0.1(8) . . . . ?
C28 C29 C30 C24 -172.9(5) . . . . ?
O4 C24 C30 N4 12.9(6) . . . . ?
C25 C24 C30 N4 -104.2(5) . . . . ?
C23 C24 C30 N4 137.6(5) . . . . ?
O4 C24 C30 C29 -173.9(5) . . . . ?
C25 C24 C30 C29 69.0(6) . . . . ?
C23 C24 C30 C29 -49.2(7) . . . . ?
C35 N5 C31 C32 0.5(8) . . . . ?
Mn3 N5 C31 C32 -177.2(4) . . . . ?
N5 C31 C32 C33 -2.5(8) . . . . ?
C31 C32 C33 C34 2.3(9) . . . . ?
C32 C33 C34 C35 -0.2(9) . . . . ?
C31 N5 C35 C34 1.7(8) . . . . ?
Mn3 N5 C35 C34 179.9(4) . . . . ?
C31 N5 C35 C37 -179.0(5) . . . . ?
Mn3 N5 C35 C37 -0.8(5) . . . . ?
C33 C34 C35 N5 -1.8(8) . . . . ?
C33 C34 C35 C37 178.9(5) . . . . ?
Mn3 O5 C37 C35 -44.0(5) . . . . ?
Mn3 O5 C37 C36 -164.8(4) . . . . ?
Mn3 O5 C37 C38 77.2(5) . . . . ?
N5 C35 C37 O5 26.9(6) . . . . ?
C34 C35 C37 O5 -153.9(5) . . . . ?
N5 C35 C37 C36 144.1(5) . . . . ?
C34 C35 C37 C36 -36.7(8) . . . . ?
N5 C35 C37 C38 -93.3(5) . . . . ?
C34 C35 C37 C38 86.0(6) . . . . ?
O5 C37 C38 C39 -66.5(6) . . . . ?
C35 C37 C38 C39 52.6(6) . . . . ?
C36 C37 C38 C39 177.1(5) . . . . ?
Mn1 O6 C39 C45 -30.9(5) . . . . ?
Mn3 O6 C39 C45 86.0(5) . . . . ?
Mn1 O6 C39 C40 85.1(5) . . . . ?
Mn3 O6 C39 C40 -158.1(3) . . . . ?
Mn1 O6 C39 C38 -157.0(3) . . . . ?
Mn3 O6 C39 C38 -40.2(6) . . . . ?
C37 C38 C39 O6 46.6(7) . . . . ?
C37 C38 C39 C45 -77.4(6) . . . . ?
C37 C38 C39 C40 164.8(5) . . . . ?
C45 N6 C41 C42 1.6(9) . . . . ?
Mn1 N6 C41 C42 161.5(5) . . . . ?
N6 C41 C42 C43 -1.3(10) . . . . ?
C41 C42 C43 C44 0.7(9) . . . . ?
C42 C43 C44 C45 -0.5(9) . . . . ?
C41 N6 C45 C44 -1.3(8) . . . . ?
Mn1 N6 C45 C44 -164.6(4) . . . . ?
C41 N6 C45 C39 173.1(5) . . . . ?
Mn1 N6 C45 C39 9.8(5) . . . . ?
C43 C44 C45 N6 0.7(8) . . . . ?
C43 C44 C45 C39 -173.2(5) . . . . ?
O6 C39 C45 N6 10.1(6) . . . . ?
C40 C39 C45 N6 -106.9(5) . . . . ?
C38 C39 C45 N6 134.6(5) . . . . ?
O6 C39 C45 C44 -175.6(5) . . . . ?
C40 C39 C45 C44 67.4(6) . . . . ?
C38 C39 C45 C44 -51.2(7) . . . . ?
C52 C47 C48 C49 -1.9(8) . . . . ?
B1 C47 C48 C49 -172.1(6) . . . . ?
C47 C48 C49 C50 0.8(9) . . . . ?
C47 C48 C49 C54 177.8(6) . . . . ?
C48 C49 C50 C51 -0.5(9) . . . . ?
C54 C49 C50 C51 -177.6(6) . . . . ?
C49 C50 C51 C52 1.5(8) . . . . ?
C49 C50 C51 C53 179.9(5) . . . . ?
C50 C51 C52 C47 -2.8(9) . . . . ?
C53 C51 C52 C47 178.8(5) . . . . ?
C48 C47 C52 C51 2.9(8) . . . . ?
B1 C47 C52 C51 173.6(5) . . . . ?
C52 C51 C53 F4 179.3(5) . . . . ?
C50 C51 C53 F4 0.8(8) . . . . ?
C52 C51 C53 F5 -59.0(7) . . . . ?
C50 C51 C53 F5 122.6(6) . . . . ?
C52 C51 C53 F6 58.7(7) . . . . ?
C50 C51 C53 F6 -119.7(6) . . . . ?
C50 C49 C54 F15B -48.8(18) . . . . ?
C48 C49 C54 F15B 134.2(16) . . . . ?
C50 C49 C54 F14A 173.2(11) . . . . ?
C48 C49 C54 F14A -3.8(14) . . . . ?
C50 C49 C54 F13B 82.2(11) . . . . ?
C48 C49 C54 F13B -94.8(11) . . . . ?
C50 C49 C54 F13A 47.1(10) . . . . ?
C48 C49 C54 F13A -129.9(9) . . . . ?
C50 C49 C54 F14B -163.7(10) . . . . ?
C48 C49 C54 F14B 19.3(12) . . . . ?
C50 C49 C54 F15A -57.4(15) . . . . ?
C48 C49 C54 F15A 125.6(14) . . . . ?
C60 C55 C56 C57 2.0(9) . . . . ?
B1 C55 C56 C57 173.9(6) . . . . ?
C55 C56 C57 C58 -1.0(11) . . . . ?
C55 C56 C57 C62 179.7(7) . . . . ?
C56 C57 C58 C59 -0.3(11) . . . . ?
C62 C57 C58 C59 179.0(7) . . . . ?
C57 C58 C59 C60 0.4(10) . . . . ?
C57 C58 C59 C61 179.1(7) . . . . ?
C58 C59 C60 C55 0.8(10) . . . . ?
C61 C59 C60 C55 -177.9(6) . . . . ?
C56 C55 C60 C59 -1.9(9) . . . . ?
B1 C55 C60 C59 -174.0(6) . . . . ?
C60 C59 C61 F2 78.9(8) . . . . ?
C58 C59 C61 F2 -99.8(8) . . . . ?
C60 C59 C61 F1 -41.4(10) . . . . ?
C58 C59 C61 F1 140.0(7) . . . . ?
C60 C59 C61 F3 -160.2(6) . . . . ?
C58 C59 C61 F3 21.1(9) . . . . ?
C56 C57 C62 F17A 27(2) . . . . ?
C58 C57 C62 F17A -152.0(17) . . . . ?
C56 C57 C62 F18A -165.5(19) . . . . ?
C58 C57 C62 F18A 15(2) . . . . ?
C56 C57 C62 F16B -40.3(14) . . . . ?
C58 C57 C62 F16B 140.4(12) . . . . ?
C56 C57 C62 F18B 177.9(12) . . . . ?
C58 C57 C62 F18B -1.4(15) . . . . ?
C56 C57 C62 F17B 75.9(10) . . . . ?
C58 C57 C62 F17B -103.3(9) . . . . ?
C56 C57 C62 F16A -80.8(10) . . . . ?
C58 C57 C62 F16A 99.9(10) . . . . ?
C68 C63 C64 C65 -0.2(9) . . . . ?
B1 C63 C64 C65 -174.1(6) . . . . ?
C63 C64 C65 C66 -2.3(10) . . . . ?
C63 C64 C65 C70 179.8(6) . . . . ?
C64 C65 C66 C67 2.2(10) . . . . ?
C70 C65 C66 C67 -179.9(6) . . . . ?
C65 C66 C67 C68 0.3(9) . . . . ?
C65 C66 C67 C69 -178.1(6) . . . . ?
C66 C67 C68 C63 -3.0(10) . . . . ?
C69 C67 C68 C63 175.5(6) . . . . ?
C64 C63 C68 C67 2.8(9) . . . . ?
B1 C63 C68 C67 176.5(6) . . . . ?
C68 C67 C69 F12 -171.5(6) . . . . ?
C66 C67 C69 F12 6.9(10) . . . . ?
C68 C67 C69 F11 56.3(9) . . . . ?
C66 C67 C69 F11 -125.2(7) . . . . ?
C68 C67 C69 F10 -58.2(8) . . . . ?
C66 C67 C69 F10 120.2(7) . . . . ?
C66 C65 C70 F20A -25(2) . . . . ?
C64 C65 C70 F20A 152.9(18) . . . . ?
C66 C65 C70 F19B -91.9(11) . . . . ?
C64 C65 C70 F19B 86.1(10) . . . . ?
C66 C65 C70 F21A 110.9(16) . . . . ?
C64 C65 C70 F21A -71.2(17) . . . . ?
C66 C65 C70 F21B 135.0(10) . . . . ?
C64 C65 C70 F21B -47.0(12) . . . . ?
C66 C65 C70 F20B 21.0(10) . . . . ?
C64 C65 C70 F20B -161.1(7) . . . . ?
C66 C65 C70 F19A -133.2(11) . . . . ?
C64 C65 C70 F19A 44.7(12) . . . . ?
C76 C71 C72 C73 1.1(10) . . . . ?
B1 C71 C72 C73 -169.7(7) . . . . ?
C71 C72 C73 C74 -1.4(11) . . . . ?
C71 C72 C73 C78 177.7(8) . . . . ?
C72 C73 C74 C75 0.4(11) . . . . ?
C78 C73 C74 C75 -178.8(8) . . . . ?
C73 C74 C75 C76 0.9(10) . . . . ?
C73 C74 C75 C77 -178.2(6) . . . . ?
C74 C75 C76 C71 -1.2(10) . . . . ?
C77 C75 C76 C71 177.9(6) . . . . ?
C72 C71 C76 C75 0.2(9) . . . . ?
B1 C71 C76 C75 171.2(6) . . . . ?
C74 C75 C77 F9 104.3(8) . . . . ?
C76 C75 C77 F9 -74.8(8) . . . . ?
C74 C75 C77 F8 -15.9(9) . . . . ?
C76 C75 C77 F8 165.0(6) . . . . ?
C74 C75 C77 F7 -136.0(7) . . . . ?
C76 C75 C77 F7 44.9(9) . . . . ?
C72 C73 C78 F24B -10.5(19) . . . . ?
C74 C73 C78 F24B 168.7(14) . . . . ?
C72 C73 C78 F23B -149.4(15) . . . . ?
C74 C73 C78 F23B 29.7(17) . . . . ?
C72 C73 C78 F23A -171.0(15) . . . . ?
C74 C73 C78 F23A 8.1(19) . . . . ?
C72 C73 C78 F24A -39.7(16) . . . . ?
C74 C73 C78 F24A 139.4(12) . . . . ?
C72 C73 C78 F22A 72.4(12) . . . . ?
C74 C73 C78 F22A -108.4(11) . . . . ?
C72 C73 C78 F22B 96.3(11) . . . . ?
C74 C73 C78 F22B -84.6(12) . . . . ?
C52 C47 B1 C55 165.0(5) . . . . ?
C48 C47 B1 C55 -25.3(8) . . . . ?
C52 C47 B1 C71 -73.6(6) . . . . ?
C48 C47 B1 C71 96.1(7) . . . . ?
C52 C47 B1 C63 48.8(8) . . . . ?
C48 C47 B1 C63 -141.4(6) . . . . ?
C56 C55 B1 C47 142.6(6) . . . . ?
C60 C55 B1 C47 -46.1(8) . . . . ?
C56 C55 B1 C71 27.3(9) . . . . ?
C60 C55 B1 C71 -161.4(6) . . . . ?
C56 C55 B1 C63 -95.7(7) . . . . ?
C60 C55 B1 C63 75.6(7) . . . . ?
C72 C71 B1 C47 94.2(7) . . . . ?
C76 C71 B1 C47 -76.0(7) . . . . ?
C72 C71 B1 C55 -145.3(6) . . . . ?
C76 C71 B1 C55 44.5(8) . . . . ?
C72 C71 B1 C63 -27.9(9) . . . . ?
C76 C71 B1 C63 161.9(6) . . . . ?
C68 C63 B1 C47 20.8(9) . . . . ?
C64 C63 B1 C47 -165.9(6) . . . . ?
C68 C63 B1 C55 -100.1(6) . . . . ?
C64 C63 B1 C55 73.2(7) . . . . ?
C68 C63 B1 C71 137.2(6) . . . . ?
C64 C63 B1 C71 -49.5(8) . . . . ?

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
O8 H8C O4 0.85(2) 2.05(4) 2.820(6) 150(6) .

_refine_diff_density_max         0.946
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.087



####################################################################### 
# 
# 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_007-16221
_database_code_depnum_ccdc_archive 'CCDC 1529460'
_audit_update_record             
;
2017-03-18 deposited with the CCDC.
2017-06-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            Tripyalk1
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H25 N3 O3'
_chemical_formula_sum            'C22 H25 N3 O3'
_chemical_formula_weight         379.45

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'
N N 0.0311 0.0180 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.1202(9)
_cell_length_b                   13.8904(2)
_cell_length_c                   10.95920(10)
_cell_angle_alpha                90
_cell_angle_beta                 104.628(7)
_cell_angle_gamma                90
_cell_volume                     1932.52(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    24312
_cell_measurement_theta_min      3.2
_cell_measurement_theta_max      66.6

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_F_000             808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.709
_shelx_estimated_absorpt_T_min   0.932
_shelx_estimated_absorpt_T_max   0.965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.865
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   'microfocus rotating anode'
_diffrn_measurement_device_type  'Rigaku Saturn 944+ CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 22.2
_diffrn_reflns_number            38183
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.482
_diffrn_reflns_theta_max         66.586
_diffrn_reflns_theta_full        66.586
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             3363
_reflns_number_gt                2826
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
; 
Dolomanov, O.V.; Bourhis, L.J.; Gildea, R.J.; Howard, J.A.K.; Puschmann, H., 
OLEX2: A complete structure solution, refinement and analysis program 
(2009). J. Appl. Cryst., 42, 339-341. 
;
_computing_publication_material  'CIFTAB-2014/2 (Sheldrick, 2014)'
_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.

 The hydrogen atoms were first found in the difference map, then generated
 geometrically and refined as riding atoms with C-H distances = 0.95- 0.99
 Å and Uiso(H) = 1.2 times Ueq(C) for CH and CH2 groups and Uiso(H)
 = 1.5 times Ueq(C) for CH3 groups. The only exceptions are H1, H2 and H3,
 which were found in the difference map and semi-freely refined with a distance
 restraint of 0.85(2) Å for O-H distances.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0363P)²+1.0498P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     SHELXT
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3363
_refine_ls_number_parameters     267
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.1026
_refine_ls_wR_factor_gt          0.0971
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.094
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.80224(10) 0.56610(9) 0.17154(12) 0.0350(3) Uani 1 1 d D . . . .
H1 H 0.7774(19) 0.5153(15) 0.128(2) 0.067(8) Uiso 1 1 d D . . . .
O2 O 0.69572(10) 0.40512(9) 0.11386(11) 0.0299(3) Uani 1 1 d D . . . .
H2 H 0.699(2) 0.3487(14) 0.077(2) 0.074(8) Uiso 1 1 d D . . . .
O3 O 0.70006(10) 0.21900(9) 0.07446(11) 0.0293(3) Uani 1 1 d D . . . .
H3 H 0.6601(17) 0.1806(16) 0.020(2) 0.062(8) Uiso 1 1 d D . . . .
N1 N 0.76890(12) 0.66521(11) 0.46071(16) 0.0379(4) Uani 1 1 d . . . . .
N2 N 0.56146(11) 0.37134(10) 0.36518(13) 0.0273(3) Uani 1 1 d . . . . .
N3 N 0.80326(12) 0.08445(11) 0.36752(15) 0.0356(4) Uani 1 1 d . . . . .
C1 C 0.82517(17) 0.72451(14) 0.5492(2) 0.0430(5) Uani 1 1 d . . . . .
H1A H 0.7920 0.7496 0.6101 0.052 Uiso 1 1 calc R U . . .
C2 C 0.92780(17) 0.75150(14) 0.5576(2) 0.0421(5) Uani 1 1 d . . . . .
H2A H 0.9636 0.7946 0.6214 0.051 Uiso 1 1 calc R U . . .
C3 C 0.97678(16) 0.71424(14) 0.47118(19) 0.0404(5) Uani 1 1 d . . . . .
H3A H 1.0479 0.7301 0.4748 0.048 Uiso 1 1 calc R U . . .
C4 C 0.92053(14) 0.65298(13) 0.37845(18) 0.0347(4) Uani 1 1 d . . . . .
H4 H 0.9529 0.6263 0.3177 0.042 Uiso 1 1 calc R U . . .
C5 C 0.81670(14) 0.63085(12) 0.37494(17) 0.0291(4) Uani 1 1 d . . . . .
C6 C 0.63999(14) 0.60401(13) 0.22760(19) 0.0372(5) Uani 1 1 d . . . . .
H6A H 0.6426 0.6711 0.2009 0.056 Uiso 1 1 calc R U . . .
H6B H 0.6046 0.6007 0.2963 0.056 Uiso 1 1 calc R U . . .
H6C H 0.6009 0.5653 0.1562 0.056 Uiso 1 1 calc R U . . .
C7 C 0.75150(13) 0.56512(12) 0.27323(17) 0.0282(4) Uani 1 1 d . . . . .
C8 C 0.75559(13) 0.46262(12) 0.32768(16) 0.0263(4) Uani 1 1 d . . . . .
H8A H 0.7300 0.4656 0.4052 0.032 Uiso 1 1 calc R U . . .
H8B H 0.8303 0.4423 0.3531 0.032 Uiso 1 1 calc R U . . .
C9 C 0.69237(13) 0.38331(12) 0.24130(15) 0.0250(4) Uani 1 1 d . . . . .
C10 C 0.74815(13) 0.28595(11) 0.28082(15) 0.0239(4) Uani 1 1 d . . . . .
H10A H 0.8230 0.2939 0.2802 0.029 Uiso 1 1 calc R U . . .
H10B H 0.7466 0.2735 0.3693 0.029 Uiso 1 1 calc R U . . .
C11 C 0.70668(13) 0.19491(12) 0.20387(15) 0.0246(4) Uani 1 1 d . . . . .
C12 C 0.60033(13) 0.15897(12) 0.21841(17) 0.0286(4) Uani 1 1 d . . . . .
H12A H 0.5460 0.2071 0.1844 0.043 Uiso 1 1 calc R U . . .
H12B H 0.6044 0.1484 0.3079 0.043 Uiso 1 1 calc R U . . .
H12C H 0.5824 0.0983 0.1722 0.043 Uiso 1 1 calc R U . . .
C13 C 0.46122(13) 0.37177(12) 0.37526(18) 0.0306(4) Uani 1 1 d . . . . .
H13 H 0.4494 0.3639 0.4567 0.037 Uiso 1 1 calc R U . . .
C14 C 0.37484(14) 0.38298(12) 0.27440(18) 0.0330(4) Uani 1 1 d . . . . .
H14 H 0.3055 0.3834 0.2862 0.040 Uiso 1 1 calc R U . . .
C15 C 0.39176(14) 0.39363(13) 0.15556(18) 0.0333(4) Uani 1 1 d . . . . .
H15 H 0.3341 0.4009 0.0837 0.040 Uiso 1 1 calc R U . . .
C16 C 0.49417(14) 0.39355(12) 0.14316(17) 0.0305(4) Uani 1 1 d . . . . .
H16 H 0.5075 0.4007 0.0623 0.037 Uiso 1 1 calc R U . . .
C17 C 0.57741(13) 0.38301(11) 0.24950(16) 0.0254(4) Uani 1 1 d . . . . .
C18 C 0.86871(15) 0.00853(14) 0.4035(2) 0.0403(5) Uani 1 1 d . . . . .
H18 H 0.8818 -0.0129 0.4884 0.048 Uiso 1 1 calc R U . . .
C19 C 0.91710(15) -0.03913(14) 0.3240(2) 0.0462(6) Uani 1 1 d . . . . .
H19 H 0.9604 -0.0936 0.3521 0.055 Uiso 1 1 calc R U . . .
C20 C 0.90139(17) -0.00624(14) 0.2038(2) 0.0462(5) Uani 1 1 d . . . . .
H20 H 0.9359 -0.0365 0.1475 0.055 Uiso 1 1 calc R U . . .
C21 C 0.83520(15) 0.07143(12) 0.16320(18) 0.0327(4) Uani 1 1 d . . . . .
H21 H 0.8238 0.0948 0.0794 0.039 Uiso 1 1 calc R U . . .
C22 C 0.78652(12) 0.11382(12) 0.24595(16) 0.0248(4) Uani 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.435(2) . ?
O1 H1 0.867(16) . ?
O2 C9 1.4405(19) . ?
O2 H2 0.888(17) . ?
O3 C11 1.4383(19) . ?
O3 H3 0.869(16) . ?
N1 C1 1.342(3) . ?
N1 C5 1.343(2) . ?
N2 C17 1.346(2) . ?
N2 C13 1.347(2) . ?
N3 C18 1.354(2) . ?
N3 C22 1.357(2) . ?
C1 C2 1.378(3) . ?
C1 H1A 0.9500 . ?
C2 C3 1.373(3) . ?
C2 H2A 0.9500 . ?
C3 C4 1.387(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.388(2) . ?
C4 H4 0.9500 . ?
C5 C7 1.525(3) . ?
C6 C7 1.521(2) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.539(2) . ?
C8 C9 1.550(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C17 1.534(2) . ?
C9 C10 1.547(2) . ?
C10 C11 1.541(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.528(2) . ?
C11 C22 1.528(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.378(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.383(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.384(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.389(2) . ?
C16 H16 0.9500 . ?
C18 C19 1.371(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.360(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.386(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.367(2) . ?
C21 H21 0.9500 . ?

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
C7 O1 H1 103.5(16) . . ?
C9 O2 H2 105.9(17) . . ?
C11 O3 H3 114.0(16) . . ?
C1 N1 C5 117.06(16) . . ?
C17 N2 C13 117.64(15) . . ?
C18 N3 C22 116.97(16) . . ?
N1 C1 C2 124.42(19) . . ?
N1 C1 H1A 117.8 . . ?
C2 C1 H1A 117.8 . . ?
C3 C2 C1 118.07(19) . . ?
C3 C2 H2A 121.0 . . ?
C1 C2 H2A 121.0 . . ?
C2 C3 C4 118.80(19) . . ?
C2 C3 H3A 120.6 . . ?
C4 C3 H3A 120.6 . . ?
C3 C4 C5 119.56(18) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
N1 C5 C4 122.06(17) . . ?
N1 C5 C7 116.71(15) . . ?
C4 C5 C7 121.23(16) . . ?
C7 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C7 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O1 C7 C6 109.73(15) . . ?
O1 C7 C5 106.09(13) . . ?
C6 C7 C5 110.07(14) . . ?
O1 C7 C8 109.40(13) . . ?
C6 C7 C8 113.11(14) . . ?
C5 C7 C8 108.19(14) . . ?
C7 C8 C9 117.37(14) . . ?
C7 C8 H8A 108.0 . . ?
C9 C8 H8A 108.0 . . ?
C7 C8 H8B 108.0 . . ?
C9 C8 H8B 108.0 . . ?
H8A C8 H8B 107.2 . . ?
O2 C9 C17 109.19(13) . . ?
O2 C9 C10 109.11(13) . . ?
C17 C9 C10 112.58(13) . . ?
O2 C9 C8 107.47(13) . . ?
C17 C9 C8 110.41(13) . . ?
C10 C9 C8 107.95(13) . . ?
C11 C10 C9 119.18(14) . . ?
C11 C10 H10A 107.5 . . ?
C9 C10 H10A 107.5 . . ?
C11 C10 H10B 107.5 . . ?
C9 C10 H10B 107.5 . . ?
H10A C10 H10B 107.0 . . ?
O3 C11 C12 110.46(14) . . ?
O3 C11 C22 109.58(13) . . ?
C12 C11 C22 107.59(13) . . ?
O3 C11 C10 105.89(13) . . ?
C12 C11 C10 114.63(13) . . ?
C22 C11 C10 108.62(13) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C13 C14 123.85(17) . . ?
N2 C13 H13 118.1 . . ?
C14 C13 H13 118.1 . . ?
C13 C14 C15 118.19(17) . . ?
C13 C14 H14 120.9 . . ?
C15 C14 H14 120.9 . . ?
C14 C15 C16 118.88(17) . . ?
C14 C15 H15 120.6 . . ?
C16 C15 H15 120.6 . . ?
C15 C16 C17 119.65(17) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
N2 C17 C16 121.78(15) . . ?
N2 C17 C9 116.41(14) . . ?
C16 C17 C9 121.81(15) . . ?
N3 C18 C19 123.53(19) . . ?
N3 C18 H18 118.2 . . ?
C19 C18 H18 118.2 . . ?
C20 C19 C18 118.17(18) . . ?
C20 C19 H19 120.9 . . ?
C18 C19 H19 120.9 . . ?
C19 C20 C21 120.12(18) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C22 C21 C20 118.82(18) . . ?
C22 C21 H21 120.6 . . ?
C20 C21 H21 120.6 . . ?
N3 C22 C21 122.32(16) . . ?
N3 C22 C11 116.53(14) . . ?
C21 C22 C11 121.11(15) . . ?

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
C5 N1 C1 C2 -0.4(3) . . . . ?
N1 C1 C2 C3 -1.1(3) . . . . ?
C1 C2 C3 C4 1.2(3) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
C1 N1 C5 C4 1.7(3) . . . . ?
C1 N1 C5 C7 -178.83(16) . . . . ?
C3 C4 C5 N1 -1.6(3) . . . . ?
C3 C4 C5 C7 178.98(16) . . . . ?
N1 C5 C7 O1 159.89(15) . . . . ?
C4 C5 C7 O1 -20.6(2) . . . . ?
N1 C5 C7 C6 41.2(2) . . . . ?
C4 C5 C7 C6 -139.28(17) . . . . ?
N1 C5 C7 C8 -82.82(18) . . . . ?
C4 C5 C7 C8 96.67(19) . . . . ?
O1 C7 C8 C9 -66.15(18) . . . . ?
C6 C7 C8 C9 56.5(2) . . . . ?
C5 C7 C8 C9 178.69(13) . . . . ?
C7 C8 C9 O2 34.07(18) . . . . ?
C7 C8 C9 C17 -84.92(17) . . . . ?
C7 C8 C9 C10 151.63(14) . . . . ?
O2 C9 C10 C11 -59.02(18) . . . . ?
C17 C9 C10 C11 62.36(19) . . . . ?
C8 C9 C10 C11 -175.52(13) . . . . ?
C9 C10 C11 O3 51.78(18) . . . . ?
C9 C10 C11 C12 -70.25(19) . . . . ?
C9 C10 C11 C22 169.40(13) . . . . ?
C17 N2 C13 C14 0.3(2) . . . . ?
N2 C13 C14 C15 0.6(3) . . . . ?
C13 C14 C15 C16 -0.6(3) . . . . ?
C14 C15 C16 C17 -0.1(3) . . . . ?
C13 N2 C17 C16 -1.1(2) . . . . ?
C13 N2 C17 C9 179.35(14) . . . . ?
C15 C16 C17 N2 1.0(3) . . . . ?
C15 C16 C17 C9 -179.46(15) . . . . ?
O2 C9 C17 N2 -174.85(13) . . . . ?
C10 C9 C17 N2 63.82(19) . . . . ?
C8 C9 C17 N2 -56.90(18) . . . . ?
O2 C9 C17 C16 5.6(2) . . . . ?
C10 C9 C17 C16 -115.75(17) . . . . ?
C8 C9 C17 C16 123.53(17) . . . . ?
C22 N3 C18 C19 -0.4(3) . . . . ?
N3 C18 C19 C20 2.4(3) . . . . ?
C18 C19 C20 C21 -2.1(3) . . . . ?
C19 C20 C21 C22 0.0(3) . . . . ?
C18 N3 C22 C21 -1.9(2) . . . . ?
C18 N3 C22 C11 175.86(15) . . . . ?
C20 C21 C22 N3 2.1(3) . . . . ?
C20 C21 C22 C11 -175.56(16) . . . . ?
O3 C11 C22 N3 178.59(14) . . . . ?
C12 C11 C22 N3 -61.27(19) . . . . ?
C10 C11 C22 N3 63.34(18) . . . . ?
O3 C11 C22 C21 -3.6(2) . . . . ?
C12 C11 C22 C21 116.51(17) . . . . ?
C10 C11 C22 C21 -118.88(17) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O2 0.867(16) 1.852(19) 2.6281(18) 148(2) .
O2 H2 O3 0.888(17) 1.802(19) 2.6241(17) 153(2) .

_refine_diff_density_max         0.251
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.043

####################################################################### 
# 
# 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_shelx_165b1_sq
_database_code_depnum_ccdc_archive 'CCDC 1529491'
_audit_update_record             
;
2017-01-24 deposited with the CCDC.
2017-06-12 downloaded from the CCDC.
;

_vrf_RINTA01_shelx_165b1_sq      
;
PROBLEM: The value of Rint is greater than 0.18
RESPONSE: The crystal was low in quality, which resulted in poor data quality. However all attempts to grow better formed crystals were unsuccessful.
;
_vrf_PLAT020_shelx_165b1_sq      
;
PROBLEM: The value of Rint is greater than 0.12 .........
0.220 Report
RESPONSE: The crystal was low in quality, which resulted in poor data quality. However all attempts to grow better formed crystals were unsuccessful.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C61 H64 Mn4 N8 O11'
_chemical_formula_weight         1304.96

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   16.9892(6)
_cell_length_b                   13.5833(5)
_cell_length_c                   33.108(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.462(6)
_cell_angle_gamma                90
_cell_volume                     7640.1(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    28846
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Plate
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.135
_exptl_crystal_F_000             2696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.698
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.776
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private Communication'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Tube'
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID imaging plate'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10
_diffrn_reflns_number            78798
_diffrn_reflns_av_unetI/netI     0.1110
_diffrn_reflns_av_R_equivalents  0.2201
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_theta_min         2.999
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             8746
_reflns_number_gt                6344
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 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. 
;

_computing_data_collection       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
; 
 'Rigaku R-AXIS RAPID, Rigaku R_AXIS RAPID imaging plate' 
;
_computing_publication_material  'SHELXL-2013/2 (Sheldrick, 2014)'
_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 

The hydrogen atoms were first found in the difference map, then generated 
geometrically and refined as riding atoms with C-H distances = 0.95 - 0.99 
angstroms and Uiso(H) = 1.2 times Ueq(C) for CH and CH2 groups and Uiso(H) 
= 1.5 times Ueq(C) for CH3 groups.

The program SQUEEZE was used to compensate for the contribution of disordered solvents contained in the voids in the crystal lattice from the diffraction intensities (Acta Cryst. 2009, D65, 148-155). This procedure was applied to the data file and the submitted model is based on the solvent removed data. Some of this disordered solvent could be modeled as water molecules, but refinement was problematic.  Based on the total electron density found in the voids (960e/ 2507 A3), it is likely that ~53 water molecules are present in the unit cell. See platon squeeze details in the .cif for more information.

;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0690P)²+165.8092P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8746
_refine_ls_number_parameters     384
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1713
_refine_ls_R_factor_gt           0.1347
_refine_ls_wR_factor_ref         0.2724
_refine_ls_wR_factor_gt          0.2513
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.089
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.37974(6) 0.48163(8) 0.62425(3) 0.0210(3) Uani 1 1 d . . . . .
Mn2 Mn 0.44356(6) 0.34065(8) 0.69031(3) 0.0211(3) Uani 1 1 d . . . . .
O1 O 0.2887(3) 0.4793(4) 0.59023(14) 0.0265(11) Uani 1 1 d . . . . .
O2 O 0.3621(3) 0.3464(3) 0.64053(13) 0.0215(10) Uani 1 1 d . . . . .
O3 O 0.4141(3) 0.6048(3) 0.60343(14) 0.0215(10) Uani 1 1 d . . . . .
O4 O 0.4591(3) 0.4872(4) 0.66671(13) 0.0224(10) Uani 1 1 d . . . . .
O5 O 0.4730(3) 0.1932(4) 0.71851(14) 0.0264(11) Uani 1 1 d . . . . .
O6 O 0.5000 0.3313(5) 0.7500 0.0265(16) Uani 1 2 d S T P . .
N1 N 0.2832(4) 0.5313(4) 0.66590(18) 0.0282(14) Uani 1 1 d . . . . .
N2 N 0.3246(4) 0.3310(4) 0.71713(17) 0.0236(13) Uani 1 1 d . . . . .
N3 N 0.4704(4) 0.4381(5) 0.57810(17) 0.0272(14) Uani 1 1 d . . . . .
N4 N 0.5560(4) 0.3381(4) 0.65681(17) 0.0257(13) Uani 1 1 d . . . . .
C1 C 0.2845(5) 0.5730(6) 0.7036(2) 0.0331(19) Uani 1 1 d . . . . .
H1 H 0.3317 0.5967 0.7141 0.040 Uiso 1 1 calc R U . . .
C2 C 0.2173(5) 0.5805(6) 0.7261(2) 0.0340(19) Uani 1 1 d . . . . .
H2 H 0.2199 0.6065 0.7521 0.041 Uiso 1 1 calc R U . . .
C3 C 0.1462(5) 0.5497(6) 0.7105(3) 0.0341(19) Uani 1 1 d . . . . .
H3 H 0.1003 0.5567 0.7253 0.041 Uiso 1 1 calc R U . . .
C4 C 0.1443(5) 0.5080(5) 0.6723(2) 0.0327(18) Uani 1 1 d . . . . .
H4 H 0.0971 0.4859 0.6611 0.039 Uiso 1 1 calc R U . . .
C5 C 0.2132(5) 0.5000(5) 0.6512(2) 0.0289(17) Uani 1 1 d . . . . .
C6 C 0.1481(5) 0.4689(6) 0.5828(3) 0.038(2) Uani 1 1 d . . . . .
H6A H 0.1435 0.5388 0.5792 0.056 Uiso 1 1 calc R U . . .
H6B H 0.1012 0.4441 0.5951 0.056 Uiso 1 1 calc R U . . .
H6C H 0.1551 0.4379 0.5570 0.056 Uiso 1 1 calc R U . . .
C7 C 0.2199(4) 0.4462(6) 0.6103(2) 0.0283(17) Uani 1 1 d . . . . .
C8 C 0.2251(4) 0.3350(5) 0.6172(2) 0.0265(16) Uani 1 1 d . . . . .
H8A H 0.2335 0.3037 0.5913 0.032 Uiso 1 1 calc R U . . .
H8B H 0.1746 0.3127 0.6270 0.032 Uiso 1 1 calc R U . . .
C9 C 0.2890(4) 0.2980(5) 0.6466(2) 0.0261(16) Uani 1 1 d . . . . .
C10 C 0.3025(5) 0.1877(5) 0.6390(2) 0.0311(18) Uani 1 1 d . . . . .
H10A H 0.3204 0.1781 0.6118 0.047 Uiso 1 1 calc R U . . .
H10B H 0.2540 0.1527 0.6427 0.047 Uiso 1 1 calc R U . . .
H10C H 0.3414 0.1634 0.6576 0.047 Uiso 1 1 calc R U . . .
C11 C 0.3081(5) 0.3370(5) 0.7570(2) 0.0314(18) Uani 1 1 d . . . . .
H11 H 0.3486 0.3538 0.7748 0.038 Uiso 1 1 calc R U . . .
C12 C 0.2349(5) 0.3197(6) 0.7726(2) 0.0332(18) Uani 1 1 d . . . . .
H12 H 0.2254 0.3254 0.8001 0.040 Uiso 1 1 calc R U . . .
C13 C 0.1754(5) 0.2933(6) 0.7457(3) 0.039(2) Uani 1 1 d . . . . .
H13 H 0.1252 0.2797 0.7551 0.046 Uiso 1 1 calc R U . . .
C14 C 0.1909(5) 0.2874(5) 0.7054(2) 0.0313(18) Uani 1 1 d . . . . .
H14 H 0.1513 0.2691 0.6873 0.038 Uiso 1 1 calc R U . . .
C15 C 0.2652(4) 0.3085(5) 0.6916(2) 0.0251(16) Uani 1 1 d . . . . .
C16 C 0.4878(5) 0.3502(6) 0.5613(2) 0.0296(17) Uani 1 1 d . . . . .
H16 H 0.4573 0.2959 0.5680 0.035 Uiso 1 1 calc R U . . .
C17 C 0.5485(5) 0.3379(6) 0.5349(2) 0.038(2) Uani 1 1 d . . . . .
H17 H 0.5603 0.2762 0.5244 0.045 Uiso 1 1 calc R U . . .
C18 C 0.5922(5) 0.4207(7) 0.5241(2) 0.037(2) Uani 1 1 d . . . . .
H18 H 0.6324 0.4151 0.5053 0.044 Uiso 1 1 calc R U . . .
C19 C 0.5757(4) 0.5104(6) 0.5412(2) 0.0277(16) Uani 1 1 d . . . . .
H19 H 0.6046 0.5659 0.5343 0.033 Uiso 1 1 calc R U . . .
C20 C 0.5149(5) 0.5166(6) 0.5691(2) 0.0295(17) Uani 1 1 d . . . . .
C21 C 0.5126(5) 0.7042(5) 0.5714(2) 0.0292(17) Uani 1 1 d . . . . .
H21A H 0.4841 0.7051 0.5463 0.044 Uiso 1 1 calc R U . . .
H21B H 0.5680 0.7086 0.5662 0.044 Uiso 1 1 calc R U . . .
H21C H 0.4967 0.7591 0.5877 0.044 Uiso 1 1 calc R U . . .
C22 C 0.4951(4) 0.6073(5) 0.5941(2) 0.0234(15) Uani 1 1 d . . . . .
C23 C 0.5449(4) 0.6068(5) 0.6333(2) 0.0223(15) Uani 1 1 d . . . . .
H23A H 0.5997 0.6140 0.6259 0.027 Uiso 1 1 calc R U . . .
H23B H 0.5307 0.6645 0.6489 0.027 Uiso 1 1 calc R U . . .
C24 C 0.5383(4) 0.5163(5) 0.6613(2) 0.0242(15) Uani 1 1 d . . . . .
C25 C 0.5710(4) 0.5470(5) 0.7035(2) 0.0228(15) Uani 1 1 d . . . . .
H25A H 0.5434 0.6043 0.7128 0.034 Uiso 1 1 calc R U . . .
H25B H 0.6261 0.5615 0.7015 0.034 Uiso 1 1 calc R U . . .
H25C H 0.5635 0.4940 0.7223 0.034 Uiso 1 1 calc R U . . .
C26 C 0.5975(5) 0.2570(5) 0.6473(2) 0.0260(16) Uani 1 1 d . . . . .
H26 H 0.5766 0.1962 0.6544 0.031 Uiso 1 1 calc R U . . .
C27 C 0.6676(5) 0.2581(6) 0.6280(2) 0.0351(19) Uani 1 1 d . . . . .
H27 H 0.6934 0.1997 0.6217 0.042 Uiso 1 1 calc R U . . .
C28 C 0.7000(4) 0.3491(6) 0.6180(2) 0.0290(17) Uani 1 1 d . . . . .
H28 H 0.7480 0.3528 0.6048 0.035 Uiso 1 1 calc R U . . .
C29 C 0.6597(5) 0.4334(6) 0.6281(2) 0.0285(17) Uani 1 1 d . . . . .
H29 H 0.6813 0.4946 0.6224 0.034 Uiso 1 1 calc R U . . .
C30 C 0.5870(4) 0.4275(5) 0.6468(2) 0.0226(15) Uani 1 1 d . . . . .
C31 C 0.5000 0.2352(7) 0.7500 0.025(2) Uani 1 2 d S T P . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mn1 O3 1.903(4) . ?
Mn1 O1 1.906(5) . ?
Mn1 O2 1.938(5) . ?
Mn1 O4 1.942(5) . ?
Mn1 N1 2.255(7) . ?
Mn1 N3 2.257(6) . ?
Mn1 Mn2 3.0965(15) . ?
Mn2 O2 2.145(5) . ?
Mn2 O4 2.155(5) . ?
Mn2 O6 2.1934(11) . ?
Mn2 N4 2.217(6) . ?
Mn2 N2 2.218(6) . ?
Mn2 O5 2.264(5) . ?
Mn2 C31 2.617(5) . ?
O1 C7 1.421(9) . ?
O2 C9 1.420(9) . ?
O3 C22 1.415(9) . ?
O4 C24 1.415(8) . ?
O5 C31 1.271(6) . ?
O6 C31 1.305(12) . ?
O6 Mn2 2.1935(11) 2_656 ?
N1 C5 1.350(10) . ?
N1 C1 1.369(10) . ?
N2 C15 1.346(9) . ?
N2 C11 1.355(9) . ?
N3 C20 1.341(10) . ?
N3 C16 1.350(10) . ?
N4 C26 1.346(9) . ?
N4 C30 1.366(9) . ?
C1 C2 1.372(11) . ?
C1 H1 0.9300 . ?
C2 C3 1.375(12) . ?
C2 H2 0.9300 . ?
C3 C4 1.386(11) . ?
C3 H3 0.9300 . ?
C4 C5 1.372(11) . ?
C4 H4 0.9300 . ?
C5 C7 1.544(11) . ?
C6 C7 1.547(10) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.530(11) . ?
C8 C9 1.536(9) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.537(10) . ?
C9 C15 1.556(10) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.371(11) . ?
C11 H11 0.9300 . ?
C12 C13 1.388(12) . ?
C12 H12 0.9300 . ?
C13 C14 1.364(11) . ?
C13 H13 0.9300 . ?
C14 C15 1.376(11) . ?
C14 H14 0.9300 . ?
C16 C17 1.369(11) . ?
C16 H16 0.9300 . ?
C17 C18 1.395(12) . ?
C17 H17 0.9300 . ?
C18 C19 1.374(11) . ?
C18 H18 0.9300 . ?
C19 C20 1.394(11) . ?
C19 H19 0.9300 . ?
C20 C22 1.523(10) . ?
C21 C22 1.544(9) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.545(9) . ?
C23 C24 1.543(10) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C30 1.541(10) . ?
C24 C25 1.555(9) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 C27 1.356(11) . ?
C26 H26 0.9300 . ?
C27 C28 1.394(11) . ?
C27 H27 0.9300 . ?
C28 C29 1.377(11) . ?
C28 H28 0.9300 . ?
C29 C30 1.388(10) . ?
C29 H29 0.9300 . ?
C31 O5 1.270(6) 2_656 ?
C31 Mn2 2.617(5) 2_656 ?

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
O3 Mn1 O1 92.9(2) . . ?
O3 Mn1 O2 169.3(2) . . ?
O1 Mn1 O2 91.3(2) . . ?
O3 Mn1 O4 90.9(2) . . ?
O1 Mn1 O4 169.7(2) . . ?
O2 Mn1 O4 86.8(2) . . ?
O3 Mn1 N1 100.7(2) . . ?
O1 Mn1 N1 77.0(2) . . ?
O2 Mn1 N1 89.9(2) . . ?
O4 Mn1 N1 92.9(2) . . ?
O3 Mn1 N3 76.8(2) . . ?
O1 Mn1 N3 98.7(2) . . ?
O2 Mn1 N3 92.8(2) . . ?
O4 Mn1 N3 91.5(2) . . ?
N1 Mn1 N3 175.0(2) . . ?
O3 Mn1 Mn2 133.87(15) . . ?
O1 Mn1 Mn2 133.22(16) . . ?
O2 Mn1 Mn2 43.23(14) . . ?
O4 Mn1 Mn2 43.57(15) . . ?
N1 Mn1 Mn2 90.31(15) . . ?
N3 Mn1 Mn2 94.54(16) . . ?
O2 Mn2 O4 76.59(17) . . ?
O2 Mn2 O6 165.72(14) . . ?
O4 Mn2 O6 109.0(2) . . ?
O2 Mn2 N4 99.76(19) . . ?
O4 Mn2 N4 74.0(2) . . ?
O6 Mn2 N4 94.45(15) . . ?
O2 Mn2 N2 74.06(19) . . ?
O4 Mn2 N2 108.3(2) . . ?
O6 Mn2 N2 91.66(15) . . ?
N4 Mn2 N2 172.3(2) . . ?
O2 Mn2 O5 119.25(18) . . ?
O4 Mn2 O5 159.87(18) . . ?
O6 Mn2 O5 58.9(2) . . ?
N4 Mn2 O5 90.2(2) . . ?
N2 Mn2 O5 89.0(2) . . ?
O2 Mn2 C31 146.2(2) . . ?
O4 Mn2 C31 137.2(2) . . ?
O6 Mn2 C31 29.9(3) . . ?
N4 Mn2 C31 93.28(15) . . ?
N2 Mn2 C31 89.71(15) . . ?
O5 Mn2 C31 29.0(2) . . ?
O2 Mn2 Mn1 38.23(12) . . ?
O4 Mn2 Mn1 38.39(12) . . ?
O6 Mn2 Mn1 145.11(19) . . ?
N4 Mn2 Mn1 87.40(15) . . ?
N2 Mn2 Mn1 90.24(15) . . ?
O5 Mn2 Mn1 155.98(13) . . ?
C31 Mn2 Mn1 174.97(19) . . ?
C7 O1 Mn1 113.3(4) . . ?
C9 O2 Mn1 128.0(4) . . ?
C9 O2 Mn2 115.7(4) . . ?
Mn1 O2 Mn2 98.5(2) . . ?
C22 O3 Mn1 113.7(4) . . ?
C24 O4 Mn1 125.1(4) . . ?
C24 O4 Mn2 115.1(4) . . ?
Mn1 O4 Mn2 98.0(2) . . ?
C31 O5 Mn2 91.1(5) . . ?
C31 O6 Mn2 93.32(18) . . ?
C31 O6 Mn2 93.32(18) . 2_656 ?
Mn2 O6 Mn2 173.4(4) . 2_656 ?
C5 N1 C1 117.8(7) . . ?
C5 N1 Mn1 109.2(5) . . ?
C1 N1 Mn1 132.4(5) . . ?
C15 N2 C11 117.7(7) . . ?
C15 N2 Mn2 116.3(5) . . ?
C11 N2 Mn2 125.6(5) . . ?
C20 N3 C16 119.1(7) . . ?
C20 N3 Mn1 109.3(5) . . ?
C16 N3 Mn1 131.5(5) . . ?
C26 N4 C30 117.9(6) . . ?
C26 N4 Mn2 125.8(5) . . ?
C30 N4 Mn2 116.3(5) . . ?
N1 C1 C2 121.3(8) . . ?
N1 C1 H1 119.4 . . ?
C2 C1 H1 119.4 . . ?
C1 C2 C3 120.3(8) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C2 C3 C4 118.7(8) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C5 C4 C3 118.9(8) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
N1 C5 C4 123.0(7) . . ?
N1 C5 C7 113.2(7) . . ?
C4 C5 C7 123.6(7) . . ?
C7 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C7 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O1 C7 C8 109.6(6) . . ?
O1 C7 C5 109.1(6) . . ?
C8 C7 C5 109.8(6) . . ?
O1 C7 C6 108.0(6) . . ?
C8 C7 C6 109.2(6) . . ?
C5 C7 C6 111.0(7) . . ?
C7 C8 C9 117.3(6) . . ?
C7 C8 H8A 108.0 . . ?
C9 C8 H8A 108.0 . . ?
C7 C8 H8B 108.0 . . ?
C9 C8 H8B 108.0 . . ?
H8A C8 H8B 107.2 . . ?
O2 C9 C8 111.9(6) . . ?
O2 C9 C10 107.3(6) . . ?
C8 C9 C10 108.8(6) . . ?
O2 C9 C15 109.1(6) . . ?
C8 C9 C15 112.9(6) . . ?
C10 C9 C15 106.6(6) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C11 C12 123.4(7) . . ?
N2 C11 H11 118.3 . . ?
C12 C11 H11 118.3 . . ?
C11 C12 C13 117.5(7) . . ?
C11 C12 H12 121.3 . . ?
C13 C12 H12 121.3 . . ?
C14 C13 C12 119.9(7) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C15 119.7(8) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
N2 C15 C14 121.7(7) . . ?
N2 C15 C9 115.0(6) . . ?
C14 C15 C9 123.0(7) . . ?
N3 C16 C17 122.7(8) . . ?
N3 C16 H16 118.7 . . ?
C17 C16 H16 118.7 . . ?
C16 C17 C18 118.1(8) . . ?
C16 C17 H17 121.0 . . ?
C18 C17 H17 121.0 . . ?
C19 C18 C17 119.9(7) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C18 C19 C20 118.8(7) . . ?
C18 C19 H19 120.6 . . ?
C20 C19 H19 120.6 . . ?
N3 C20 C19 121.4(7) . . ?
N3 C20 C22 113.3(6) . . ?
C19 C20 C22 125.2(7) . . ?
C22 C21 H21A 109.5 . . ?
C22 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C22 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O3 C22 C20 108.5(6) . . ?
O3 C22 C21 108.6(6) . . ?
C20 C22 C21 112.5(6) . . ?
O3 C22 C23 110.0(6) . . ?
C20 C22 C23 109.4(6) . . ?
C21 C22 C23 107.9(6) . . ?
C24 C23 C22 117.9(6) . . ?
C24 C23 H23A 107.8 . . ?
C22 C23 H23A 107.8 . . ?
C24 C23 H23B 107.8 . . ?
C22 C23 H23B 107.8 . . ?
H23A C23 H23B 107.2 . . ?
O4 C24 C30 109.5(6) . . ?
O4 C24 C23 111.8(6) . . ?
C30 C24 C23 113.2(6) . . ?
O4 C24 C25 107.1(5) . . ?
C30 C24 C25 107.5(6) . . ?
C23 C24 C25 107.4(6) . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N4 C26 C27 124.4(7) . . ?
N4 C26 H26 117.8 . . ?
C27 C26 H26 117.8 . . ?
C26 C27 C28 118.1(7) . . ?
C26 C27 H27 120.9 . . ?
C28 C27 H27 120.9 . . ?
C29 C28 C27 118.8(7) . . ?
C29 C28 H28 120.6 . . ?
C27 C28 H28 120.6 . . ?
C28 C29 C30 120.5(7) . . ?
C28 C29 H29 119.8 . . ?
C30 C29 H29 119.8 . . ?
N4 C30 C29 120.3(7) . . ?
N4 C30 C24 114.3(6) . . ?
C29 C30 C24 125.2(7) . . ?
O5 C31 O5 126.6(9) 2_656 . ?
O5 C31 O6 116.7(5) 2_656 . ?
O5 C31 O6 116.7(5) . . ?
O5 C31 Mn2 173.2(6) 2_656 . ?
O5 C31 Mn2 59.9(3) . . ?
O6 C31 Mn2 56.81(18) . . ?
O5 C31 Mn2 59.9(3) 2_656 2_656 ?
O5 C31 Mn2 173.2(6) . 2_656 ?
O6 C31 Mn2 56.81(18) . 2_656 ?
Mn2 C31 Mn2 113.6(4) . 2_656 ?

_refine_diff_density_max         1.612
_refine_diff_density_min         -0.837
_refine_diff_density_rms         0.135



####################################################################### 
# 
# 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_mini_167B1
_database_code_depnum_ccdc_archive 'CCDC 1529489'
_audit_update_record             
;
2017-03-18 deposited with the CCDC.
2017-06-12 downloaded from the CCDC.
;

_vrf_PLAT058_mini_167B1          
;
PROBLEM: Maximum Transmission Factor Missing ............          ?
RESPONSE: The maximum transmission factor was lost due to a hard drive failure.
Unfortunately, the raw data was not retrievable. The only surviving
information is the absorption corrected HKL.
;
_vrf_PLAT059_mini_167B1          
;
PROBLEM: Minimum Transmission Factor Missing ............          ?
RESPONSE: The minimum transmission factor was lost due to a hard drive failure.
Unfortunately, the raw data was not retrievable. The only surviving
information is the absorption corrected HKL.
;
_vrf_PLAT183_mini_167B1          
;
PROBLEM: Missing _cell_measurement_reflns_used value ....     Please Do !
RESPONSE: The number of reflections used to determine the unit cell
was lost due to a hard drive failure. Unfortunately, the raw data was not
retrievable. The only surviving information is the absorption corrected HKL.
;
_vrf_PLAT184_mini_167B1          
;
PROBLEM: Missing _cell_measurement_theta_min value ......     Please Do !
RESPONSE: The minimum theta value used to determine the unit cell
was lost due to a hard drive failure. Unfortunately, the raw data was not
retrievable. The only surviving information is the absorption corrected HKL.
;
_vrf_PLAT185_mini_167B1          
;
PROBLEM: Missing _cell_measurement_theta_max value ......

RESPONSE: The maximum theta value used to determine the unit cell
was lost due to a hard drive failure. Unfortunately, the raw data was not
retrievable. The only surviving information is the absorption corrected HKL.
;
_vrf_PLAT417_mini_167B1          
;
PROBLEM: Short Inter D-H..H-D       H3B    ..  H4B

RESPONSE: The water protons are likely disordered, see checkCIF alert PLAT976.
;
_vrf_PLAT976_mini_167B1          
;
PROBLEM: 

RESPONSE: The water protons are likely disordered.
;
_vrf_PLAT975_mini_167B1          
;
PROBLEM: 

RESPONSE: The water protons are likely disordered.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H32 Cu2 N4 O4, 4(H2 O)'
_chemical_formula_sum            'C30 H40 Cu2 N4 O8'
_chemical_formula_weight         711.74

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.1205(6)
_cell_length_b                   12.7849(8)
_cell_length_c                   11.5863(8)
_cell_angle_alpha                90
_cell_angle_beta                 96.938(7)
_cell_angle_gamma                90
_cell_volume                     1488.17(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Block
_exptl_crystal_colour            Blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.588
_exptl_crystal_F_000             740
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.488
_shelx_estimated_absorpt_T_min   0.755
_shelx_estimated_absorpt_T_max   0.865
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Mercury275R CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 6.8
_diffrn_reflns_number            25325
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.187
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3407
_reflns_number_gt                3182
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
; 
 'Rigaku SCX Mini, Rigaku Mercury275R CCD' 
;
_computing_publication_material  'CIFTAB-2013/2 (Sheldrick, 2014)'
_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 

 The hydrogen atoms were first found in the difference map, then generated 
 geometrically and refined as riding atoms with C-H distances = 0.95- 0.99 
 Å and Uiso(H) = 1.2 times Ueq(C) for CH and CH2 groups and Uiso(H) 
 = 1.5 times Ueq(C) for CH3 groups. The risidual electron density near O3 and O4
 were assumed to be the hydrogen atoms of the water molecules. The water protons were
 generated geometrically and refined as riding atoms. The water molecules were 
 constrained to behave as a rigid body.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0403P)²+2.0239P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     SHELXT
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3407
_refine_ls_number_parameters     207
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0352
_refine_ls_wR_factor_ref         0.0932
_refine_ls_wR_factor_gt          0.0914
_refine_ls_goodness_of_fit_ref   1.164
_refine_ls_restrained_S_all      1.164
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.87111(3) 0.46942(2) 0.43791(2) 0.01300(10) Uani 1 1 d . . . . .
O1 O 0.71112(15) 0.43750(13) 0.50586(14) 0.0173(3) Uani 1 1 d . . . . .
O2 O 0.96360(15) 0.50680(13) 0.62449(14) 0.0146(3) Uani 1 1 d . . . . .
N1 N 0.89006(18) 0.31236(15) 0.43830(16) 0.0143(4) Uani 1 1 d . . . . .
N2 N 1.16014(18) 0.38103(15) 0.60922(17) 0.0147(4) Uani 1 1 d . . . . .
C1 C 0.9634(2) 0.25156(19) 0.3764(2) 0.0171(5) Uani 1 1 d . . . . .
H1 H 1.0200 0.2837 0.3271 0.021 Uiso 1 1 calc R U . . .
C2 C 0.9592(2) 0.14352(19) 0.3821(2) 0.0195(5) Uani 1 1 d . . . . .
H2 H 1.0102 0.1019 0.3359 0.023 Uiso 1 1 calc R U . . .
C3 C 0.8791(2) 0.0974(2) 0.4566(2) 0.0205(5) Uani 1 1 d . . . . .
H3 H 0.8745 0.0233 0.4623 0.025 Uiso 1 1 calc R U . . .
C4 C 0.8059(2) 0.16026(19) 0.5229(2) 0.0184(5) Uani 1 1 d . . . . .
H4 H 0.7521 0.1299 0.5758 0.022 Uiso 1 1 calc R U . . .
C5 C 0.8120(2) 0.26805(18) 0.51091(19) 0.0149(4) Uani 1 1 d . . . . .
C6 C 0.6028(2) 0.2996(2) 0.5998(2) 0.0232(5) Uani 1 1 d . . . . .
H6A H 0.5508 0.3523 0.6360 0.035 Uiso 1 1 calc R U . . .
H6B H 0.6190 0.2395 0.6520 0.035 Uiso 1 1 calc R U . . .
H6C H 0.5533 0.2768 0.5261 0.035 Uiso 1 1 calc R U . . .
C7 C 0.7365(2) 0.34712(19) 0.5765(2) 0.0170(5) Uani 1 1 d . . . . .
C8 C 0.8186(2) 0.3740(2) 0.6951(2) 0.0182(5) Uani 1 1 d . . . . .
H8A H 0.8255 0.3092 0.7421 0.022 Uiso 1 1 calc R U . . .
H8B H 0.7653 0.4242 0.7353 0.022 Uiso 1 1 calc R U . . .
C9 C 0.9619(2) 0.42028(18) 0.6995(2) 0.0156(4) Uani 1 1 d . . . . .
C10 C 1.0047(2) 0.4556(2) 0.8262(2) 0.0207(5) Uani 1 1 d . . . . .
H10A H 1.0955 0.4836 0.8328 0.031 Uiso 1 1 calc R U . . .
H10B H 1.0021 0.3956 0.8785 0.031 Uiso 1 1 calc R U . . .
H10C H 0.9439 0.5100 0.8475 0.031 Uiso 1 1 calc R U . . .
C11 C 1.2591(2) 0.31957(19) 0.5815(2) 0.0184(5) Uani 1 1 d . . . . .
H11 H 1.3231 0.3483 0.5370 0.022 Uiso 1 1 calc R U . . .
C12 C 1.2713(2) 0.21602(19) 0.6155(2) 0.0213(5) Uani 1 1 d . . . . .
H12 H 1.3415 0.1737 0.5938 0.026 Uiso 1 1 calc R U . . .
C13 C 1.1783(2) 0.17555(19) 0.6823(2) 0.0209(5) Uani 1 1 d . . . . .
H13 H 1.1851 0.1051 0.7085 0.025 Uiso 1 1 calc R U . . .
C14 C 1.0751(2) 0.23852(19) 0.7104(2) 0.0184(5) Uani 1 1 d . . . . .
H14 H 1.0108 0.2116 0.7559 0.022 Uiso 1 1 calc R U . . .
C15 C 1.0671(2) 0.34104(18) 0.67159(19) 0.0149(4) Uani 1 1 d . . . . .
O3 O 0.7739(3) 0.6352(2) 0.7053(2) 0.0487(6) Uani 1 1 d G . . . .
H3A H 0.8301 0.5998 0.6728 0.073 Uiso 1 1 d G U . . .
H3B H 0.6968 0.6091 0.6885 0.073 Uiso 1 1 d G U . . .
O4 O 0.9698(2) 0.05085(19) 0.86683(18) 0.0363(5) Uani 1 1 d G . . . .
H4A H 1.0442 0.0645 0.9101 0.054 Uiso 1 1 d G U . . .
H4B H 0.9166 0.0176 0.9078 0.054 Uiso 1 1 d G 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
Cu1 O2 1.9250(16) 3_766 ?
Cu1 O1 1.9276(16) . ?
Cu1 N2 2.0031(19) 3_766 ?
Cu1 N1 2.017(2) . ?
Cu1 O2 2.2998(16) . ?
Cu1 Cu1 2.9294(6) 3_766 ?
O1 C7 1.421(3) . ?
O2 C9 1.408(3) . ?
O2 Cu1 1.9250(16) 3_766 ?
N1 C1 1.341(3) . ?
N1 C5 1.346(3) . ?
N2 C11 1.342(3) . ?
N2 C15 1.354(3) . ?
N2 Cu1 2.0031(19) 3_766 ?
C1 C2 1.384(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.386(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.387(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.387(3) . ?
C4 H4 0.9500 . ?
C5 C7 1.525(3) . ?
C6 C7 1.536(3) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.556(3) . ?
C8 C9 1.561(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C15 1.533(3) . ?
C9 C10 1.547(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.382(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.389(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.388(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.385(3) . ?
C14 H14 0.9500 . ?
O3 H3A 0.8497 . ?
O3 H3B 0.8501 . ?
O4 H4A 0.8701 . ?
O4 H4B 0.8700 . ?

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 Cu1 O1 176.12(7) 3_766 . ?
O2 Cu1 N2 82.10(7) 3_766 3_766 ?
O1 Cu1 N2 101.58(7) . 3_766 ?
O2 Cu1 N1 94.09(7) 3_766 . ?
O1 Cu1 N1 82.68(7) . . ?
N2 Cu1 N1 164.30(8) 3_766 . ?
O2 Cu1 O2 92.67(6) 3_766 . ?
O1 Cu1 O2 85.80(6) . . ?
N2 Cu1 O2 95.21(7) 3_766 . ?
N1 Cu1 O2 100.19(7) . . ?
O2 Cu1 Cu1 51.65(5) 3_766 3_766 ?
O1 Cu1 Cu1 126.73(5) . 3_766 ?
N2 Cu1 Cu1 88.91(6) 3_766 3_766 ?
N1 Cu1 Cu1 100.71(5) . 3_766 ?
O2 Cu1 Cu1 41.03(4) . 3_766 ?
C7 O1 Cu1 107.77(13) . . ?
C9 O2 Cu1 115.60(13) . 3_766 ?
C9 O2 Cu1 112.51(13) . . ?
Cu1 O2 Cu1 87.32(6) 3_766 . ?
C1 N1 C5 119.6(2) . . ?
C1 N1 Cu1 129.40(16) . . ?
C5 N1 Cu1 110.95(15) . . ?
C11 N2 C15 119.6(2) . . ?
C11 N2 Cu1 126.26(16) . 3_766 ?
C15 N2 Cu1 114.13(15) . 3_766 ?
N1 C1 C2 122.1(2) . . ?
N1 C1 H1 118.9 . . ?
C2 C1 H1 118.9 . . ?
C1 C2 C3 118.5(2) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C2 C3 C4 119.3(2) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C3 C4 C5 119.2(2) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
N1 C5 C4 121.1(2) . . ?
N1 C5 C7 113.6(2) . . ?
C4 C5 C7 125.3(2) . . ?
C7 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C7 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O1 C7 C5 108.59(18) . . ?
O1 C7 C6 108.73(19) . . ?
C5 C7 C6 109.3(2) . . ?
O1 C7 C8 111.63(19) . . ?
C5 C7 C8 109.87(18) . . ?
C6 C7 C8 108.66(19) . . ?
C7 C8 C9 120.50(18) . . ?
C7 C8 H8A 107.2 . . ?
C9 C8 H8A 107.2 . . ?
C7 C8 H8B 107.2 . . ?
C9 C8 H8B 107.2 . . ?
H8A C8 H8B 106.8 . . ?
O2 C9 C15 109.16(18) . . ?
O2 C9 C10 109.47(19) . . ?
C15 C9 C10 105.71(18) . . ?
O2 C9 C8 110.99(18) . . ?
C15 C9 C8 114.15(19) . . ?
C10 C9 C8 107.14(18) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C11 C12 122.4(2) . . ?
N2 C11 H11 118.8 . . ?
C12 C11 H11 118.8 . . ?
C11 C12 C13 118.1(2) . . ?
C11 C12 H12 120.9 . . ?
C13 C12 H12 120.9 . . ?
C14 C13 C12 119.7(2) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C15 C14 C13 119.2(2) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
N2 C15 C14 120.9(2) . . ?
N2 C15 C9 114.1(2) . . ?
C14 C15 C9 124.9(2) . . ?
H3A O3 H3B 109.5 . . ?
H4A O4 H4B 109.4 . . ?

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
C5 N1 C1 C2 1.8(3) . . . . ?
Cu1 N1 C1 C2 -176.12(17) . . . . ?
N1 C1 C2 C3 -1.7(4) . . . . ?
C1 C2 C3 C4 0.1(4) . . . . ?
C2 C3 C4 C5 1.5(3) . . . . ?
C1 N1 C5 C4 -0.1(3) . . . . ?
Cu1 N1 C5 C4 178.15(17) . . . . ?
C1 N1 C5 C7 179.1(2) . . . . ?
Cu1 N1 C5 C7 -2.6(2) . . . . ?
C3 C4 C5 N1 -1.5(3) . . . . ?
C3 C4 C5 C7 179.3(2) . . . . ?
Cu1 O1 C7 C5 -43.28(19) . . . . ?
Cu1 O1 C7 C6 -162.13(15) . . . . ?
Cu1 O1 C7 C8 78.00(18) . . . . ?
N1 C5 C7 O1 30.2(2) . . . . ?
C4 C5 C7 O1 -150.6(2) . . . . ?
N1 C5 C7 C6 148.7(2) . . . . ?
C4 C5 C7 C6 -32.1(3) . . . . ?
N1 C5 C7 C8 -92.1(2) . . . . ?
C4 C5 C7 C8 87.1(3) . . . . ?
O1 C7 C8 C9 -62.2(3) . . . . ?
C5 C7 C8 C9 58.4(3) . . . . ?
C6 C7 C8 C9 177.9(2) . . . . ?
Cu1 O2 C9 C15 -24.6(2) 3_766 . . . ?
Cu1 O2 C9 C15 73.56(18) . . . . ?
Cu1 O2 C9 C10 90.63(18) 3_766 . . . ?
Cu1 O2 C9 C10 -171.18(14) . . . . ?
Cu1 O2 C9 C8 -151.31(14) 3_766 . . . ?
Cu1 O2 C9 C8 -53.1(2) . . . . ?
C7 C8 C9 O2 50.8(3) . . . . ?
C7 C8 C9 C15 -73.0(3) . . . . ?
C7 C8 C9 C10 170.3(2) . . . . ?
C15 N2 C11 C12 -0.8(3) . . . . ?
Cu1 N2 C11 C12 -178.34(18) 3_766 . . . ?
N2 C11 C12 C13 -1.0(4) . . . . ?
C11 C12 C13 C14 1.5(4) . . . . ?
C12 C13 C14 C15 -0.2(4) . . . . ?
C11 N2 C15 C14 2.1(3) . . . . ?
Cu1 N2 C15 C14 179.98(17) 3_766 . . . ?
C11 N2 C15 C9 178.6(2) . . . . ?
Cu1 N2 C15 C9 -3.5(2) 3_766 . . . ?
C13 C14 C15 N2 -1.7(3) . . . . ?
C13 C14 C15 C9 -177.8(2) . . . . ?
O2 C9 C15 N2 17.7(3) . . . . ?
C10 C9 C15 N2 -100.0(2) . . . . ?
C8 C9 C15 N2 142.6(2) . . . . ?
O2 C9 C15 C14 -165.9(2) . . . . ?
C10 C9 C15 C14 76.4(3) . . . . ?
C8 C9 C15 C14 -41.1(3) . . . . ?

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
O3 H3B O4 0.85 1.88 2.729(3) 173.3 2_656
O4 H4A O1 0.87 1.91 2.763(3) 167.7 4_666
O4 H4B O1 0.87 2.01 2.877(3) 176.8 2_646
O3 H3A O2 0.85 1.93 2.774(3) 170.0 .

_refine_diff_density_max         0.534
_refine_diff_density_min         -0.753
_refine_diff_density_rms         0.084

####################################################################### 
# 
# 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_007-17008-T2
_database_code_depnum_ccdc_archive 'CCDC 1529461'
_audit_update_record             
;
2017-03-18 deposited with the CCDC.
2017-06-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H25 N3 O3, H2 O'
_chemical_formula_sum            'C22 H27 N3 O4'
_chemical_formula_weight         397.46

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'
N N 0.0311 0.0180 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   10.84070(10)
_cell_length_b                   15.3854(2)
_cell_length_c                   24.0090(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4004.4(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    32082
_cell_measurement_theta_min      1.8
_cell_measurement_theta_max      66.5

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_F_000             1696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.745
_shelx_estimated_absorpt_T_min   0.865
_shelx_estimated_absorpt_T_max   0.865
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.605
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   'microfocus rotating anode'
_diffrn_measurement_device_type  'Rigaku Saturn 944+ CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 22.2
_diffrn_reflns_number            124474
_diffrn_reflns_av_unetI/netI     0.0529
_diffrn_reflns_av_R_equivalents  0.1646
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.682
_diffrn_reflns_theta_max         66.603
_diffrn_reflns_theta_full        66.603
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3547
_reflns_number_gt                2799
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
; 
Dolomanov, O.V.; Bourhis, L.J.; Gildea, R.J.; Howard, J.A.K.; Puschmann, H., 
OLEX2: A complete structure solution, refinement and analysis program 
(2009). J. Appl. Cryst., 42, 339-341. 
;
_computing_publication_material  'CIFTAB-2014/2 (Sheldrick, 2014)'
_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 

The hydrogen atoms were first found in the difference map, then generated 
geometrically and refined as riding atoms with C-H distances = 0.95 - 0.99 
angstroms and Uiso(H) = 1.2 times Ueq(C) for CH and CH2 groups and Uiso(H) 
= 1.5 times Ueq(C) for CH3 groups. The only exceptions are hydrogens associated with
oxygen atoms. These atoms were found in the difference map and semi-freely refined
with O-H distance restraints of 0.85(2) Angstroms.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1325P)²+0.7873P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     SHELXT
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0019(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3547
_refine_ls_number_parameters     285
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0771
_refine_ls_R_factor_gt           0.0673
_refine_ls_wR_factor_ref         0.2094
_refine_ls_wR_factor_gt          0.1974
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_restrained_S_all      1.117
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.39156(18) 0.19753(12) 0.49058(7) 0.0463(5) Uani 1 1 d D . . . .
H1 H 0.322(3) 0.225(3) 0.488(2) 0.109(16) Uiso 1 1 d D . . . .
O2 O 0.20667(16) 0.27562(12) 0.43053(7) 0.0432(5) Uani 1 1 d D . . . .
H2 H 0.134(2) 0.293(3) 0.4194(17) 0.091(13) Uiso 1 1 d D . . . .
O3 O 0.03821(17) 0.33845(13) 0.36117(8) 0.0515(5) Uani 1 1 d D . . . .
H3 H -0.0407(19) 0.327(2) 0.3556(14) 0.075(11) Uiso 1 1 d D . . . .
N1 N 0.6822(2) 0.19031(14) 0.42238(9) 0.0466(5) Uani 1 1 d . . . . .
N2 N 0.40721(19) 0.41824(13) 0.34970(9) 0.0418(5) Uani 1 1 d . . . . .
N3 N 0.2182(2) 0.41351(14) 0.24233(9) 0.0444(5) Uani 1 1 d . . . . .
C1 C 0.7709(3) 0.13017(19) 0.41498(11) 0.0503(7) Uani 1 1 d . . . . .
H1A H 0.8503 0.1496 0.4037 0.060 Uiso 1 1 calc R U . . .
C2 C 0.7540(3) 0.04248(18) 0.42268(10) 0.0482(6) Uani 1 1 d . . . . .
H2A H 0.8199 0.0026 0.4174 0.058 Uiso 1 1 calc R U . . .
C3 C 0.6376(3) 0.01385(17) 0.43843(11) 0.0469(6) Uani 1 1 d . . . . .
H3A H 0.6211 -0.0464 0.4430 0.056 Uiso 1 1 calc R U . . .
C4 C 0.5465(2) 0.07516(16) 0.44721(11) 0.0431(6) Uani 1 1 d . . . . .
H4 H 0.4664 0.0572 0.4584 0.052 Uiso 1 1 calc R U . . .
C5 C 0.5714(2) 0.16273(15) 0.43973(10) 0.0391(6) Uani 1 1 d . . . . .
C6 C 0.5261(3) 0.31765(16) 0.46724(11) 0.0466(6) Uani 1 1 d . . . . .
H6A H 0.4594 0.3573 0.4779 0.070 Uiso 1 1 calc R U . . .
H6B H 0.5744 0.3435 0.4370 0.070 Uiso 1 1 calc R U . . .
H6C H 0.5798 0.3074 0.4994 0.070 Uiso 1 1 calc R U . . .
C7 C 0.4713(2) 0.23147(15) 0.44772(10) 0.0399(6) Uani 1 1 d . . . . .
C8 C 0.4019(2) 0.23753(16) 0.39175(10) 0.0386(6) Uani 1 1 d . . . . .
H8A H 0.4626 0.2556 0.3632 0.046 Uiso 1 1 calc R U . . .
H8B H 0.3751 0.1780 0.3819 0.046 Uiso 1 1 calc R U . . .
C9 C 0.2890(2) 0.29730(15) 0.38573(9) 0.0384(6) Uani 1 1 d . . . . .
C10 C 0.2278(2) 0.27537(16) 0.32909(10) 0.0408(6) Uani 1 1 d . . . . .
H10A H 0.2905 0.2838 0.2996 0.049 Uiso 1 1 calc R U . . .
H10B H 0.2062 0.2129 0.3294 0.049 Uiso 1 1 calc R U . . .
C11 C 0.1119(2) 0.32647(17) 0.31229(10) 0.0434(6) Uani 1 1 d . . . . .
C12 C 0.0407(3) 0.27433(19) 0.26834(12) 0.0526(7) Uani 1 1 d . . . . .
H12A H 0.0127 0.2193 0.2846 0.079 Uiso 1 1 calc R U . . .
H12B H 0.0948 0.2623 0.2365 0.079 Uiso 1 1 calc R U . . .
H12C H -0.0308 0.3080 0.2558 0.079 Uiso 1 1 calc R U . . .
C13 C 0.4410(2) 0.50200(17) 0.35019(12) 0.0472(6) Uani 1 1 d . . . . .
H13 H 0.4985 0.5210 0.3229 0.057 Uiso 1 1 calc R U . . .
C14 C 0.3975(3) 0.56250(17) 0.38799(12) 0.0490(7) Uani 1 1 d . . . . .
H14 H 0.4259 0.6209 0.3872 0.059 Uiso 1 1 calc R U . . .
C15 C 0.3116(2) 0.53589(17) 0.42706(11) 0.0474(6) Uani 1 1 d . . . . .
H15 H 0.2790 0.5758 0.4534 0.057 Uiso 1 1 calc R U . . .
C16 C 0.2740(2) 0.44964(17) 0.42686(10) 0.0435(6) Uani 1 1 d . . . . .
H16 H 0.2146 0.4296 0.4530 0.052 Uiso 1 1 calc R U . . .
C17 C 0.3242(2) 0.39308(15) 0.38813(9) 0.0368(5) Uani 1 1 d . . . . .
C18 C 0.2504(3) 0.48950(18) 0.21920(11) 0.0500(7) Uani 1 1 d . . . . .
H18 H 0.3054 0.4885 0.1884 0.060 Uiso 1 1 calc R U . . .
C19 C 0.2082(3) 0.56910(19) 0.23760(12) 0.0548(7) Uani 1 1 d . . . . .
H19 H 0.2333 0.6215 0.2200 0.066 Uiso 1 1 calc R U . . .
C20 C 0.1284(3) 0.57002(18) 0.28232(12) 0.0544(7) Uani 1 1 d . . . . .
H20 H 0.0950 0.6234 0.2954 0.065 Uiso 1 1 calc R U . . .
C21 C 0.0973(3) 0.49268(18) 0.30799(11) 0.0486(6) Uani 1 1 d . . . . .
H21 H 0.0446 0.4927 0.3396 0.058 Uiso 1 1 calc R U . . .
C22 C 0.1434(2) 0.41481(16) 0.28732(10) 0.0416(6) Uani 1 1 d . . . . .
H4A H -0.254(4) 0.283(3) 0.3681(15) 0.130(19) Uiso 1 1 d D . . . .
O4 O -0.2020(2) 0.3092(2) 0.34744(15) 0.1129(13) Uani 1 1 d D . . . .
H4B H -0.238(4) 0.331(3) 0.3190(12) 0.100(14) Uiso 1 1 d D . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.442(3) . ?
O1 H1 0.866(19) . ?
O2 C9 1.437(3) . ?
O2 H2 0.877(19) . ?
O3 C11 1.432(3) . ?
O3 H3 0.884(19) . ?
N1 C5 1.339(3) . ?
N1 C1 1.347(3) . ?
N2 C13 1.340(3) . ?
N2 C17 1.345(3) . ?
N3 C18 1.341(3) . ?
N3 C22 1.351(3) . ?
C1 C2 1.374(4) . ?
C1 H1A 0.9500 . ?
C2 C3 1.389(4) . ?
C2 H2A 0.9500 . ?
C3 C4 1.382(4) . ?
C3 H3A 0.9500 . ?
C4 C5 1.386(3) . ?
C4 H4 0.9500 . ?
C5 C7 1.528(3) . ?
C6 C7 1.527(3) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.543(3) . ?
C8 C9 1.538(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C17 1.524(3) . ?
C9 C10 1.550(3) . ?
C10 C11 1.536(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C22 1.524(3) . ?
C11 C12 1.534(4) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.383(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.384(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.388(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.385(3) . ?
C16 H16 0.9500 . ?
C18 C19 1.380(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.379(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.382(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.390(4) . ?
C21 H21 0.9500 . ?
O4 H4A 0.847(19) . ?
O4 H4B 0.854(18) . ?

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
C7 O1 H1 107(3) . . ?
C9 O2 H2 105(3) . . ?
C11 O3 H3 113(2) . . ?
C5 N1 C1 117.6(2) . . ?
C13 N2 C17 117.0(2) . . ?
C18 N3 C22 118.3(2) . . ?
N1 C1 C2 124.1(3) . . ?
N1 C1 H1A 117.9 . . ?
C2 C1 H1A 117.9 . . ?
C1 C2 C3 118.0(2) . . ?
C1 C2 H2A 121.0 . . ?
C3 C2 H2A 121.0 . . ?
C4 C3 C2 118.3(2) . . ?
C4 C3 H3A 120.8 . . ?
C2 C3 H3A 120.8 . . ?
C3 C4 C5 120.3(2) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
N1 C5 C4 121.6(2) . . ?
N1 C5 C7 117.2(2) . . ?
C4 C5 C7 121.2(2) . . ?
C7 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C7 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O1 C7 C6 109.2(2) . . ?
O1 C7 C5 105.36(18) . . ?
C6 C7 C5 111.3(2) . . ?
O1 C7 C8 110.58(19) . . ?
C6 C7 C8 113.9(2) . . ?
C5 C7 C8 106.18(19) . . ?
C9 C8 C7 120.4(2) . . ?
C9 C8 H8A 107.2 . . ?
C7 C8 H8A 107.2 . . ?
C9 C8 H8B 107.2 . . ?
C7 C8 H8B 107.2 . . ?
H8A C8 H8B 106.9 . . ?
O2 C9 C17 110.62(19) . . ?
O2 C9 C8 106.57(18) . . ?
C17 C9 C8 112.0(2) . . ?
O2 C9 C10 109.93(19) . . ?
C17 C9 C10 110.54(19) . . ?
C8 C9 C10 107.02(19) . . ?
C11 C10 C9 118.0(2) . . ?
C11 C10 H10A 107.8 . . ?
C9 C10 H10A 107.8 . . ?
C11 C10 H10B 107.8 . . ?
C9 C10 H10B 107.8 . . ?
H10A C10 H10B 107.2 . . ?
O3 C11 C22 109.4(2) . . ?
O3 C11 C12 110.5(2) . . ?
C22 C11 C12 108.0(2) . . ?
O3 C11 C10 107.88(19) . . ?
C22 C11 C10 112.1(2) . . ?
C12 C11 C10 108.9(2) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C13 C14 124.0(3) . . ?
N2 C13 H13 118.0 . . ?
C14 C13 H13 118.0 . . ?
C13 C14 C15 118.4(2) . . ?
C13 C14 H14 120.8 . . ?
C15 C14 H14 120.8 . . ?
C14 C15 C16 118.5(2) . . ?
C14 C15 H15 120.7 . . ?
C16 C15 H15 120.7 . . ?
C17 C16 C15 119.2(2) . . ?
C17 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
N2 C17 C16 122.8(2) . . ?
N2 C17 C9 114.9(2) . . ?
C16 C17 C9 122.3(2) . . ?
N3 C18 C19 123.7(3) . . ?
N3 C18 H18 118.1 . . ?
C19 C18 H18 118.1 . . ?
C20 C19 C18 117.8(3) . . ?
C20 C19 H19 121.1 . . ?
C18 C19 H19 121.1 . . ?
C19 C20 C21 119.5(3) . . ?
C19 C20 H20 120.3 . . ?
C21 C20 H20 120.3 . . ?
C20 C21 C22 119.7(3) . . ?
C20 C21 H21 120.2 . . ?
C22 C21 H21 120.2 . . ?
N3 C22 C21 120.9(2) . . ?
N3 C22 C11 115.8(2) . . ?
C21 C22 C11 123.2(2) . . ?
H4A O4 H4B 111(3) . . ?

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
O4 H4B N3 0.854(18) 2.00(2) 2.823(3) 161(4) 6_556
O4 H4A N1 0.847(19) 2.06(2) 2.857(3) 157(5) 1_455
O2 H2 O3 0.877(19) 1.87(3) 2.654(3) 147(4) .
O1 H1 O2 0.866(19) 2.02(3) 2.746(3) 141(4) .
O3 H3 O4 0.884(19) 1.78(2) 2.663(3) 177(4) .

_refine_diff_density_max         0.316
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.064

####################################################################### 
# 
# 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_spider-16001
_database_code_depnum_ccdc_archive 'CCDC 1529495'
_audit_update_record             
;
2017-03-18 deposited with the CCDC.
2017-06-12 downloaded from the CCDC.
;

_vrf_PLAT869_spider-16001        
;
PROBLEM: ALERTS Related to the use of SQUEEZE Suppressed  
RESPONSE: See the "_refine_special_details" and "_platon_squeeze_details"
of the .cif.
;

_vrf_PLAT605_spider-16001        
;
PROBLEM: SQUEEZE voids
RESPONSE: See the "_refine_special_details" and "_platon_squeeze_details"
of the .cif.
;

_vrf_PLAT910_spider-16001        
;
PROBLEM: Missing # of FCF Reflections Below Th(Min) 
RESPONSE: These data were collected with an image plate detector. It is not 
possible to increase the distance from the crystal to the detector, 
which prevented the collection of additional images to overcome
this alert. However this does not present a problem since there are 19783
independent reflections and a data/parameter ratio of ~19. 
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C44 H44 Mn2 N6 O6, C H2 Cl2'
_chemical_formula_sum            'C45 H46 Cl2 Mn2 N6 O6'
_chemical_formula_weight         947.66

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   19.8078(6)
_cell_length_b                   15.0917(4)
_cell_length_c                   29.829(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.066(7)
_cell_angle_gamma                90
_cell_volume                     8867.0(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    57849
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_F_000             3920
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.745
_shelx_estimated_absorpt_T_min   0.865
_shelx_estimated_absorpt_T_max   0.865
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.844
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Tube'
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID imaging plate'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10
_diffrn_reflns_number            101124
_diffrn_reflns_av_unetI/netI     0.0774
_diffrn_reflns_av_R_equivalents  0.0980
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         3.029
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             19783
_reflns_number_gt                12603
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 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. 
;

_computing_data_collection       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
; 
 'Rigaku R-AXIS RAPID, Rigaku R_AXIS RAPID imaging plate' 
;
_computing_publication_material  'CIFTAB-2013/2 (Sheldrick, 2014)'
_refine_special_details          
;  Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 

 The hydrogen atoms were first found in the difference map, then generated 
 geometrically and refined as riding atoms with C-H distances = 0.95- 0.99 
 Å and Uiso(H) = 1.2 times Ueq(C) for CH and CH2 groups and Uiso(H) 
 = 1.5 times Ueq(C) for CH3 groups. 

Several reflections with Error/esd > 10
 were omitted during refinement. These 
reflections may have been due to the 
 significant ice buildup on the loop during 
data collection or improper 
 recorded due to the beam stop.


 
The program SQUEEZE was used to compensate for the contribution of disordered
 
solvents contained in the voids in the crystal lattice from the diffraction 
 
intensities (Acta Cryst. 2009, D65, 148-155). This procedure was applied to the 
 
data file and the submitted model is based on the solvent removed data. Based 
 on 
the total electron density found in the voids (33e/ 440 A3), it is likely 
 that ~2 
water molecules are present in the unit cell. See platon squeeze details 
 in the 
.cif for more information.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0453P)²+11.6414P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     SHELXT
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         19783
_refine_ls_number_parameters     1107
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1011
_refine_ls_R_factor_gt           0.0520
_refine_ls_wR_factor_ref         0.1322
_refine_ls_wR_factor_gt          0.1054
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.29939(3) 0.71219(3) 0.62866(2) 0.01527(11) Uani 1 1 d . . . . .
Mn2 Mn 0.42458(3) 0.59920(3) 0.62823(2) 0.01509(11) Uani 1 1 d . . . . .
O1 O 0.28780(12) 0.82281(14) 0.65602(7) 0.0184(5) Uani 1 1 d . . . . .
O2 O 0.39368(11) 0.70695(14) 0.65612(7) 0.0155(5) Uani 1 1 d . . . . .
O3 O 0.50791(12) 0.59762(14) 0.66413(8) 0.0189(5) Uani 1 1 d . . . . .
O4 O 0.21072(12) 0.69503(14) 0.60122(7) 0.0179(5) Uani 1 1 d . . . . .
O5 O 0.32995(11) 0.60379(14) 0.60161(7) 0.0158(5) Uani 1 1 d . . . . .
O6 O 0.44530(11) 0.50732(14) 0.59035(8) 0.0173(5) Uani 1 1 d . . . . .
N1 N 0.32701(14) 0.81015(18) 0.57546(9) 0.0176(6) Uani 1 1 d . . . . .
N2 N 0.46114(14) 0.71224(18) 0.58644(9) 0.0166(6) Uani 1 1 d . . . . .
N3 N 0.63895(16) 0.7675(2) 0.67392(11) 0.0281(7) Uani 1 1 d . . . . .
N4 N 0.24582(14) 0.63454(18) 0.68203(9) 0.0177(6) Uani 1 1 d . . . . .
N5 N 0.36691(14) 0.50722(17) 0.67172(9) 0.0166(6) Uani 1 1 d . . . . .
N6 N 0.37284(17) 0.28566(19) 0.58924(11) 0.0287(7) Uani 1 1 d . . . . .
C1 C 0.32884(18) 0.8032(2) 0.53104(11) 0.0204(7) Uani 1 1 d . . . . .
H1 H 0.3215 0.7467 0.5174 0.025 Uiso 1 1 calc R U . . .
C2 C 0.34090(19) 0.8745(2) 0.50408(12) 0.0249(8) Uani 1 1 d . . . . .
H2 H 0.3406 0.8677 0.4724 0.030 Uiso 1 1 calc R U . . .
C3 C 0.3535(2) 0.9561(2) 0.52428(13) 0.0301(9) Uani 1 1 d . . . . .
H3 H 0.3623 1.0064 0.5066 0.036 Uiso 1 1 calc R U . . .
C4 C 0.3532(2) 0.9637(2) 0.57067(13) 0.0284(9) Uani 1 1 d . . . . .
H4 H 0.3621 1.0192 0.5851 0.034 Uiso 1 1 calc R U . . .
C5 C 0.33961(18) 0.8895(2) 0.59563(12) 0.0199(7) Uani 1 1 d . . . . .
C6 C 0.3137(2) 0.9762(2) 0.66435(13) 0.0247(8) Uani 1 1 d . . . . .
H6A H 0.2694 0.9920 0.6486 0.037 Uiso 1 1 calc R U . . .
H6B H 0.3470 1.0220 0.6589 0.037 Uiso 1 1 calc R U . . .
H6C H 0.3101 0.9716 0.6968 0.037 Uiso 1 1 calc R U . . .
C7 C 0.33687(18) 0.8862(2) 0.64653(11) 0.0189(7) Uani 1 1 d . . . . .
C8 C 0.40766(18) 0.8631(2) 0.67149(11) 0.0189(7) Uani 1 1 d . . . . .
H8A H 0.4388 0.9128 0.6669 0.023 Uiso 1 1 calc R U . . .
H8B H 0.4029 0.8601 0.7042 0.023 Uiso 1 1 calc R U . . .
C9 C 0.44178(18) 0.7774(2) 0.65825(11) 0.0179(7) Uani 1 1 d . . . . .
C10 C 0.49860(17) 0.7504(2) 0.69528(11) 0.0193(7) Uani 1 1 d . . . . .
H10A H 0.4773 0.7368 0.7230 0.023 Uiso 1 1 calc R U . . .
H10B H 0.5285 0.8024 0.7019 0.023 Uiso 1 1 calc R U . . .
C11 C 0.54427(18) 0.6699(2) 0.68499(12) 0.0202(7) Uani 1 1 d . . . . .
C12 C 0.57886(19) 0.6365(2) 0.73048(12) 0.0253(8) Uani 1 1 d . . . . .
H12A H 0.5442 0.6156 0.7492 0.038 Uiso 1 1 calc R U . . .
H12B H 0.6047 0.6849 0.7460 0.038 Uiso 1 1 calc R U . . .
H12C H 0.6096 0.5876 0.7253 0.038 Uiso 1 1 calc R U . . .
C13 C 0.48503(18) 0.7111(2) 0.54621(11) 0.0199(7) Uani 1 1 d . . . . .
H13 H 0.4781 0.6595 0.5281 0.024 Uiso 1 1 calc R U . . .
C14 C 0.51929(19) 0.7814(2) 0.52975(12) 0.0237(8) Uani 1 1 d . . . . .
H14 H 0.5340 0.7796 0.5005 0.028 Uiso 1 1 calc R U . . .
C15 C 0.5315(2) 0.8549(2) 0.55735(12) 0.0275(9) Uani 1 1 d . . . . .
H15 H 0.5558 0.9040 0.5473 0.033 Uiso 1 1 calc R U . . .
C16 C 0.50833(19) 0.8566(2) 0.59946(12) 0.0227(8) Uani 1 1 d . . . . .
H16 H 0.5174 0.9059 0.6190 0.027 Uiso 1 1 calc R U . . .
C17 C 0.47140(17) 0.7844(2) 0.61262(11) 0.0171(7) Uani 1 1 d . . . . .
C18 C 0.6889(2) 0.7954(2) 0.65007(14) 0.0297(9) Uani 1 1 d . . . . .
H18 H 0.7176 0.8418 0.6624 0.036 Uiso 1 1 calc R U . . .
C19 C 0.7011(2) 0.7611(2) 0.60915(14) 0.0301(9) Uani 1 1 d . . . . .
H19 H 0.7359 0.7849 0.5931 0.036 Uiso 1 1 calc R U . . .
C20 C 0.66160(19) 0.6912(2) 0.59171(13) 0.0249(8) Uani 1 1 d . . . . .
H20 H 0.6690 0.6655 0.5636 0.030 Uiso 1 1 calc R U . . .
C21 C 0.61077(18) 0.6593(2) 0.61623(12) 0.0210(7) Uani 1 1 d . . . . .
H21 H 0.5837 0.6103 0.6054 0.025 Uiso 1 1 calc R U . . .
C22 C 0.60007(18) 0.6997(2) 0.65655(12) 0.0209(7) Uani 1 1 d . . . . .
C23 C 0.25774(19) 0.6252(2) 0.72666(12) 0.0227(8) Uani 1 1 d . . . . .
H23 H 0.2976 0.6514 0.7416 0.027 Uiso 1 1 calc R U . . .
C24 C 0.2152(2) 0.5796(2) 0.75239(13) 0.0267(8) Uani 1 1 d . . . . .
H24 H 0.2251 0.5751 0.7842 0.032 Uiso 1 1 calc R U . . .
C25 C 0.1576(2) 0.5404(2) 0.73041(12) 0.0277(9) Uani 1 1 d . . . . .
H25 H 0.1272 0.5088 0.7471 0.033 Uiso 1 1 calc R U . . .
C26 C 0.14460(18) 0.5477(2) 0.68395(12) 0.0218(8) Uani 1 1 d . . . . .
H26 H 0.1060 0.5199 0.6683 0.026 Uiso 1 1 calc R U . . .
C27 C 0.18912(18) 0.5966(2) 0.66075(12) 0.0189(7) Uani 1 1 d . . . . .
C28 C 0.10925(18) 0.6112(2) 0.58897(13) 0.0245(8) Uani 1 1 d . . . . .
H28A H 0.0833 0.6544 0.6047 0.037 Uiso 1 1 calc R U . . .
H28B H 0.0897 0.5520 0.5918 0.037 Uiso 1 1 calc R U . . .
H28C H 0.1073 0.6272 0.5570 0.037 Uiso 1 1 calc R U . . .
C29 C 0.18279(17) 0.6110(2) 0.60972(11) 0.0167(7) Uani 1 1 d . . . . .
C30 C 0.22016(17) 0.5354(2) 0.58656(11) 0.0174(7) Uani 1 1 d . . . . .
H30A H 0.1962 0.4793 0.5915 0.021 Uiso 1 1 calc R U . . .
H30B H 0.2146 0.5469 0.5537 0.021 Uiso 1 1 calc R U . . .
C31 C 0.29607(16) 0.5204(2) 0.60081(11) 0.0142(7) Uani 1 1 d . . . . .
C32 C 0.32569(17) 0.4650(2) 0.56425(11) 0.0182(7) Uani 1 1 d . . . . .
H32A H 0.3188 0.4984 0.5356 0.022 Uiso 1 1 calc R U . . .
H32B H 0.2988 0.4097 0.5600 0.022 Uiso 1 1 calc R U . . .
C33 C 0.40175(17) 0.4390(2) 0.57249(11) 0.0166(7) Uani 1 1 d . . . . .
C34 C 0.42437(19) 0.4149(2) 0.52619(11) 0.0231(8) Uani 1 1 d . . . . .
H34A H 0.4187 0.4665 0.5062 0.035 Uiso 1 1 calc R U . . .
H34B H 0.3965 0.3658 0.5130 0.035 Uiso 1 1 calc R U . . .
H34C H 0.4722 0.3971 0.5299 0.035 Uiso 1 1 calc R U . . .
C35 C 0.38672(18) 0.4714(2) 0.71205(11) 0.0203(7) Uani 1 1 d . . . . .
H35 H 0.4258 0.4946 0.7293 0.024 Uiso 1 1 calc R U . . .
C36 C 0.35215(19) 0.4015(2) 0.72958(12) 0.0231(8) Uani 1 1 d . . . . .
H36 H 0.3666 0.3778 0.7585 0.028 Uiso 1 1 calc R U . . .
C37 C 0.29625(19) 0.3673(2) 0.70370(12) 0.0250(8) Uani 1 1 d . . . . .
H37 H 0.2719 0.3189 0.7145 0.030 Uiso 1 1 calc R U . . .
C38 C 0.27578(19) 0.4040(2) 0.66172(12) 0.0221(8) Uani 1 1 d . . . . .
H38 H 0.2377 0.3807 0.6435 0.027 Uiso 1 1 calc R U . . .
C39 C 0.31179(17) 0.4753(2) 0.64680(11) 0.0148(7) Uani 1 1 d . . . . .
C40 C 0.3820(2) 0.2120(2) 0.61387(14) 0.0336(10) Uani 1 1 d . . . . .
H40 H 0.3541 0.1624 0.6052 0.040 Uiso 1 1 calc R U . . .
C41 C 0.4292(2) 0.2029(2) 0.65098(14) 0.0313(9) Uani 1 1 d . . . . .
H41 H 0.4341 0.1486 0.6671 0.038 Uiso 1 1 calc R U . . .
C42 C 0.4692(2) 0.2756(2) 0.66387(13) 0.0282(9) Uani 1 1 d . . . . .
H42 H 0.5025 0.2722 0.6892 0.034 Uiso 1 1 calc R U . . .
C43 C 0.46013(19) 0.3534(2) 0.63927(12) 0.0222(8) Uani 1 1 d . . . . .
H43 H 0.4868 0.4042 0.6477 0.027 Uiso 1 1 calc R U . . .
C44 C 0.41177(17) 0.3562(2) 0.60229(11) 0.0181(7) Uani 1 1 d . . . . .
Mn3 Mn 0.08299(3) 0.64370(3) 0.38558(2) 0.01785(12) Uani 1 1 d . . . . .
Mn4 Mn 0.21173(3) 0.74931(3) 0.39992(2) 0.01660(12) Uani 1 1 d . . . . .
O7 O 0.05519(12) 0.54299(15) 0.41464(8) 0.0201(5) Uani 1 1 d . . . . .
O8 O 0.17515(11) 0.63496(14) 0.41559(7) 0.0171(5) Uani 1 1 d . . . . .
O9 O 0.29703(12) 0.71839(14) 0.42877(7) 0.0181(5) Uani 1 1 d . . . . .
O10 O 0.00414(12) 0.65732(15) 0.34675(8) 0.0231(5) Uani 1 1 d . . . . .
O11 O 0.11956(12) 0.75842(14) 0.36895(7) 0.0181(5) Uani 1 1 d . . . . .
O12 O 0.23093(12) 0.86576(15) 0.38263(8) 0.0215(5) Uani 1 1 d . . . . .
N7 N 0.04009(18) 0.4060(2) 0.35471(12) 0.0371(8) Uani 1 1 d . . . . .
N8 N 0.14024(15) 0.56231(18) 0.33777(9) 0.0193(6) Uani 1 1 d . . . . .
N9 N 0.26727(14) 0.68945(17) 0.34324(9) 0.0174(6) Uani 1 1 d . . . . .
N10 N -0.12353(17) 0.8277(2) 0.35654(13) 0.0373(9) Uani 1 1 d . . . . .
N11 N 0.04817(14) 0.74242(18) 0.43586(10) 0.0200(6) Uani 1 1 d . . . . .
N12 N 0.18204(14) 0.83324(18) 0.45953(9) 0.0188(6) Uani 1 1 d . . . . .
C45 C 0.0284(2) 0.3340(3) 0.32537(13) 0.0307(9) Uani 1 1 d . . . . .
H45 H 0.0006 0.3407 0.2976 0.037 Uiso 1 1 calc R U . . .
C46 C 0.0575(2) 0.2536(3) 0.33702(15) 0.0401(11) Uani 1 1 d . . . . .
H46 H 0.0499 0.2035 0.3179 0.048 Uiso 1 1 calc R U . . .
C47 C 0.0979(2) 0.2481(3) 0.37711(16) 0.0421(11) Uani 1 1 d . . . . .
H47 H 0.1180 0.1924 0.3852 0.051 Uiso 1 1 calc R U . . .
C48 C 0.11096(18) 0.3151(2) 0.40549(12) 0.0195(7) Uani 1 1 d . . . . .
H48 H 0.1397 0.3076 0.4328 0.023 Uiso 1 1 calc R U . . .
C49 C 0.08243(18) 0.3936(2) 0.39452(12) 0.0209(7) Uani 1 1 d . . . . .
C50 C 0.06606(19) 0.4363(2) 0.47253(12) 0.0247(8) Uani 1 1 d . . . . .
H50A H 0.0730 0.4823 0.4958 0.037 Uiso 1 1 calc R U . . .
H50B H 0.0899 0.3822 0.4832 0.037 Uiso 1 1 calc R U . . .
H50C H 0.0174 0.4239 0.4662 0.037 Uiso 1 1 calc R U . . .
C51 C 0.09398(17) 0.4685(2) 0.42947(11) 0.0182(7) Uani 1 1 d . . . . .
C52 C 0.17116(17) 0.4865(2) 0.44114(11) 0.0183(7) Uani 1 1 d . . . . .
H52A H 0.1780 0.5096 0.4724 0.022 Uiso 1 1 calc R U . . .
H52B H 0.1951 0.4289 0.4410 0.022 Uiso 1 1 calc R U . . .
C53 C 0.20603(17) 0.5504(2) 0.41099(11) 0.0175(7) Uani 1 1 d . . . . .
C54 C 0.28188(17) 0.5568(2) 0.42863(11) 0.0189(7) Uani 1 1 d . . . . .
H54A H 0.3046 0.5024 0.4193 0.023 Uiso 1 1 calc R U . . .
H54B H 0.2855 0.5569 0.4620 0.023 Uiso 1 1 calc R U . . .
C55 C 0.32257(18) 0.6379(2) 0.41349(11) 0.0176(7) Uani 1 1 d . . . . .
C56 C 0.39610(18) 0.6285(2) 0.43510(12) 0.0219(8) Uani 1 1 d . . . . .
H56A H 0.4229 0.6790 0.4264 0.033 Uiso 1 1 calc R U . . .
H56B H 0.4156 0.5734 0.4247 0.033 Uiso 1 1 calc R U . . .
H56C H 0.3967 0.6269 0.4680 0.033 Uiso 1 1 calc R U . . .
C57 C 0.12196(18) 0.5387(2) 0.29496(11) 0.0210(7) Uani 1 1 d . . . . .
H57 H 0.0848 0.5684 0.2787 0.025 Uiso 1 1 calc R U . . .
C58 C 0.1548(2) 0.4729(3) 0.27348(12) 0.0286(9) Uani 1 1 d . . . . .
H58 H 0.1416 0.4586 0.2428 0.034 Uiso 1 1 calc R U . . .
C59 C 0.2074(2) 0.4287(2) 0.29785(13) 0.0285(9) Uani 1 1 d . . . . .
H59 H 0.2303 0.3821 0.2843 0.034 Uiso 1 1 calc R U . . .
C60 C 0.22671(19) 0.4526(2) 0.34206(12) 0.0240(8) Uani 1 1 d . . . . .
H60 H 0.2632 0.4231 0.3591 0.029 Uiso 1 1 calc R U . . .
C61 C 0.19186(18) 0.5203(2) 0.36114(11) 0.0177(7) Uani 1 1 d . . . . .
C62 C 0.25751(18) 0.6972(2) 0.29856(11) 0.0202(7) Uani 1 1 d . . . . .
H62 H 0.2203 0.7316 0.2856 0.024 Uiso 1 1 calc R U . . .
C63 C 0.29976(19) 0.6569(2) 0.27021(12) 0.0242(8) Uani 1 1 d . . . . .
H63 H 0.2928 0.6646 0.2385 0.029 Uiso 1 1 calc R U . . .
C64 C 0.35219(19) 0.6052(2) 0.28991(12) 0.0236(8) Uani 1 1 d . . . . .
H64 H 0.3818 0.5764 0.2716 0.028 Uiso 1 1 calc R U . . .
C65 C 0.36192(18) 0.5952(2) 0.33644(12) 0.0205(7) Uani 1 1 d . . . . .
H65 H 0.3971 0.5584 0.3502 0.025 Uiso 1 1 calc R U . . .
C66 C 0.31900(17) 0.6401(2) 0.36209(11) 0.0160(7) Uani 1 1 d . . . . .
C67 C -0.1753(2) 0.8419(3) 0.38185(17) 0.0437(12) Uani 1 1 d . . . . .
H67 H -0.2016 0.8940 0.3763 0.052 Uiso 1 1 calc R U . . .
C68 C -0.1920(2) 0.7857(3) 0.41499(16) 0.0393(11) Uani 1 1 d . . . . .
H68 H -0.2285 0.7992 0.4320 0.047 Uiso 1 1 calc R U . . .
C69 C -0.1548(2) 0.7096(3) 0.42305(14) 0.0315(9) Uani 1 1 d . . . . .
H69 H -0.1650 0.6692 0.4458 0.038 Uiso 1 1 calc R U . . .
C70 C -0.10178(19) 0.6928(2) 0.39707(13) 0.0274(8) Uani 1 1 d . . . . .
H70 H -0.0760 0.6398 0.4015 0.033 Uiso 1 1 calc R U . . .
C71 C -0.08663(19) 0.7538(2) 0.36462(13) 0.0264(8) Uani 1 1 d . . . . .
C72 C -0.0649(2) 0.7233(3) 0.28617(14) 0.0356(10) Uani 1 1 d . . . . .
H72A H -0.0305 0.7083 0.2660 0.053 Uiso 1 1 calc R U . . .
H72B H -0.0883 0.7778 0.2756 0.053 Uiso 1 1 calc R U . . .
H72C H -0.0978 0.6748 0.2862 0.053 Uiso 1 1 calc R U . . .
C73 C -0.03026(19) 0.7373(2) 0.33422(13) 0.0253(8) Uani 1 1 d . . . . .
C74 C 0.01741(19) 0.8199(2) 0.33333(12) 0.0243(8) Uani 1 1 d . . . . .
H74A H 0.0388 0.8181 0.3048 0.029 Uiso 1 1 calc R U . . .
H74B H -0.0114 0.8736 0.3324 0.029 Uiso 1 1 calc R U . . .
C75 C 0.07405(18) 0.8307(2) 0.37213(12) 0.0211(7) Uani 1 1 d . . . . .
C76 C 0.11304(18) 0.9175(2) 0.36716(12) 0.0220(8) Uani 1 1 d . . . . .
H76A H 0.0836 0.9668 0.3751 0.026 Uiso 1 1 calc R U . . .
H76B H 0.1196 0.9244 0.3349 0.026 Uiso 1 1 calc R U . . .
C77 C 0.18348(19) 0.9291(2) 0.39505(12) 0.0217(8) Uani 1 1 d . . . . .
C78 C 0.2121(2) 1.0198(2) 0.38436(14) 0.0296(9) Uani 1 1 d . . . . .
H78A H 0.2569 1.0274 0.4013 0.044 Uiso 1 1 calc R U . . .
H78B H 0.1815 1.0663 0.3929 0.044 Uiso 1 1 calc R U . . .
H78C H 0.2164 1.0238 0.3520 0.044 Uiso 1 1 calc R U . . .
C79 C 0.02190(17) 0.7279(2) 0.47438(12) 0.0220(8) Uani 1 1 d . . . . .
H79 H 0.0253 0.6700 0.4869 0.026 Uiso 1 1 calc R U . . .
C80 C -0.01011(19) 0.7925(2) 0.49711(13) 0.0256(8) Uani 1 1 d . . . . .
H80 H -0.0267 0.7804 0.5252 0.031 Uiso 1 1 calc R U . . .
C81 C -0.01727(19) 0.8757(2) 0.47754(14) 0.0289(9) Uani 1 1 d . . . . .
H81 H -0.0401 0.9215 0.4917 0.035 Uiso 1 1 calc R U . . .
C82 C 0.00934(18) 0.8915(2) 0.43677(13) 0.0249(8) Uani 1 1 d . . . . .
H82 H 0.0046 0.9479 0.4227 0.030 Uiso 1 1 calc R U . . .
C83 C 0.04277(17) 0.8234(2) 0.41727(12) 0.0191(7) Uani 1 1 d . . . . .
C84 C 0.17732(18) 0.8150(2) 0.50272(12) 0.0236(8) Uani 1 1 d . . . . .
H84 H 0.1791 0.7547 0.5119 0.028 Uiso 1 1 calc R U . . .
C85 C 0.16989(19) 0.8791(3) 0.53495(13) 0.0295(9) Uani 1 1 d . . . . .
H85 H 0.1671 0.8636 0.5656 0.035 Uiso 1 1 calc R U . . .
C86 C 0.1666(2) 0.9666(3) 0.52110(13) 0.0308(9) Uani 1 1 d . . . . .
H86 H 0.1619 1.0126 0.5423 0.037 Uiso 1 1 calc R U . . .
C87 C 0.1703(2) 0.9869(3) 0.47593(13) 0.0289(9) Uani 1 1 d . . . . .
H87 H 0.1677 1.0467 0.4659 0.035 Uiso 1 1 calc R U . . .
C88 C 0.17773(18) 0.9188(2) 0.44589(12) 0.0213(8) Uani 1 1 d . . . . .
Cl1 Cl 0.11604(5) 0.79673(6) 0.71066(3) 0.0338(2) Uani 1 1 d . . . . .
Cl2 Cl 0.10251(6) 0.94954(7) 0.64974(4) 0.0424(3) Uani 1 1 d . . . . .
C89 C 0.1264(2) 0.8368(2) 0.65614(13) 0.0322(9) Uani 1 1 d . . . . .
H89A H 0.0984 0.8008 0.6335 0.039 Uiso 1 1 calc R U . . .
H89B H 0.1745 0.8301 0.6505 0.039 Uiso 1 1 calc R U . . .
Cl3 Cl 0.44756(6) 0.90477(7) 0.41407(3) 0.0371(2) Uani 1 1 d . . . . .
Cl4 Cl 0.39284(7) 0.92700(10) 0.32063(4) 0.0622(4) Uani 1 1 d . . . . .
C90 C 0.3899(2) 0.8635(3) 0.36982(13) 0.0308(9) Uani 1 1 d . . . . .
H90A H 0.4013 0.8011 0.3636 0.037 Uiso 1 1 calc R U . . .
H90B H 0.3433 0.8649 0.3790 0.037 Uiso 1 1 calc 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
Mn1 O4 1.876(2) . ?
Mn1 O1 1.883(2) . ?
Mn1 O5 1.949(2) . ?
Mn1 O2 1.960(2) . ?
Mn1 N1 2.277(3) . ?
Mn1 N4 2.322(3) . ?
Mn1 Mn2 3.0107(7) . ?
Mn2 O6 1.862(2) . ?
Mn2 O3 1.870(2) . ?
Mn2 O2 1.954(2) . ?
Mn2 O5 1.958(2) . ?
Mn2 N2 2.276(3) . ?
Mn2 N5 2.286(3) . ?
O1 C7 1.414(4) . ?
O2 C9 1.424(4) . ?
O3 C11 1.414(4) . ?
O4 C29 1.417(4) . ?
O5 C31 1.425(4) . ?
O6 C33 1.412(4) . ?
N1 C1 1.333(4) . ?
N1 C5 1.351(4) . ?
N2 C13 1.336(4) . ?
N2 C17 1.343(4) . ?
N3 C18 1.346(5) . ?
N3 C22 1.351(4) . ?
N4 C23 1.335(4) . ?
N4 C27 1.357(4) . ?
N5 C35 1.340(4) . ?
N5 C39 1.343(4) . ?
N6 C40 1.334(5) . ?
N6 C44 1.348(4) . ?
C1 C2 1.379(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.382(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.389(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.387(5) . ?
C4 H4 0.9500 . ?
C5 C7 1.526(5) . ?
C6 C7 1.545(4) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.556(5) . ?
C8 C9 1.530(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C17 1.542(4) . ?
C9 C10 1.546(5) . ?
C10 C11 1.565(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C22 1.530(5) . ?
C11 C12 1.539(5) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.377(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.387(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.382(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.391(5) . ?
C16 H16 0.9500 . ?
C18 C19 1.370(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.382(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.391(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.384(5) . ?
C21 H21 0.9500 . ?
C23 C24 1.383(5) . ?
C23 H23 0.9500 . ?
C24 C25 1.386(5) . ?
C24 H24 0.9500 . ?
C25 C26 1.387(5) . ?
C25 H25 0.9500 . ?
C26 C27 1.389(5) . ?
C26 H26 0.9500 . ?
C27 C29 1.530(5) . ?
C28 C29 1.521(5) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 C30 1.560(4) . ?
C30 C31 1.535(5) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 C39 1.534(4) . ?
C31 C32 1.539(4) . ?
C32 C33 1.551(5) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C44 1.534(5) . ?
C33 C34 1.540(4) . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 C36 1.390(5) . ?
C35 H35 0.9500 . ?
C36 C37 1.381(5) . ?
C36 H36 0.9500 . ?
C37 C38 1.390(5) . ?
C37 H37 0.9500 . ?
C38 C39 1.390(5) . ?
C38 H38 0.9500 . ?
C40 C41 1.378(6) . ?
C40 H40 0.9500 . ?
C41 C42 1.384(6) . ?
C41 H41 0.9500 . ?
C42 C43 1.387(5) . ?
C42 H42 0.9500 . ?
C43 C44 1.383(5) . ?
C43 H43 0.9500 . ?
Mn3 O10 1.855(2) . ?
Mn3 O7 1.862(2) . ?
Mn3 O8 1.951(2) . ?
Mn3 O11 1.961(2) . ?
Mn3 N11 2.272(3) . ?
Mn3 N8 2.274(3) . ?
Mn3 Mn4 2.9993(7) . ?
Mn4 O9 1.872(2) . ?
Mn4 O12 1.882(2) . ?
Mn4 O8 1.948(2) . ?
Mn4 O11 1.962(2) . ?
Mn4 N9 2.297(3) . ?
Mn4 N12 2.309(3) . ?
O7 C51 1.406(4) . ?
O8 C53 1.428(4) . ?
O9 C55 1.410(4) . ?
O10 C73 1.416(4) . ?
O11 C75 1.425(4) . ?
O12 C77 1.417(4) . ?
N7 C49 1.392(5) . ?
N7 C45 1.398(5) . ?
N8 C61 1.335(4) . ?
N8 C57 1.338(4) . ?
N9 C62 1.332(4) . ?
N9 C66 1.341(4) . ?
N10 C71 1.342(5) . ?
N10 C67 1.352(6) . ?
N11 C79 1.329(4) . ?
N11 C83 1.342(4) . ?
N12 C84 1.330(4) . ?
N12 C88 1.354(4) . ?
C45 C46 1.372(6) . ?
C45 H45 0.9500 . ?
C46 C47 1.369(6) . ?
C46 H46 0.9500 . ?
C47 C48 1.327(5) . ?
C47 H47 0.9500 . ?
C48 C49 1.338(5) . ?
C48 H48 0.9500 . ?
C49 C51 1.538(5) . ?
C50 C51 1.530(4) . ?
C50 H50A 0.9800 . ?
C50 H50B 0.9800 . ?
C50 H50C 0.9800 . ?
C51 C52 1.555(5) . ?
C52 C53 1.532(4) . ?
C52 H52A 0.9900 . ?
C52 H52B 0.9900 . ?
C53 C54 1.542(5) . ?
C53 C61 1.552(5) . ?
C54 C55 1.558(5) . ?
C54 H54A 0.9900 . ?
C54 H54B 0.9900 . ?
C55 C66 1.528(5) . ?
C55 C56 1.536(5) . ?
C56 H56A 0.9800 . ?
C56 H56B 0.9800 . ?
C56 H56C 0.9800 . ?
C57 C58 1.381(5) . ?
C57 H57 0.9500 . ?
C58 C59 1.378(5) . ?
C58 H58 0.9500 . ?
C59 C60 1.381(5) . ?
C59 H59 0.9500 . ?
C60 C61 1.388(5) . ?
C60 H60 0.9500 . ?
C62 C63 1.391(5) . ?
C62 H62 0.9500 . ?
C63 C64 1.379(5) . ?
C63 H63 0.9500 . ?
C64 C65 1.389(5) . ?
C64 H64 0.9500 . ?
C65 C66 1.380(5) . ?
C65 H65 0.9500 . ?
C67 C68 1.369(6) . ?
C67 H67 0.9500 . ?
C68 C69 1.373(6) . ?
C68 H68 0.9500 . ?
C69 C70 1.392(5) . ?
C69 H69 0.9500 . ?
C70 C71 1.391(5) . ?
C70 H70 0.9500 . ?
C71 C73 1.531(5) . ?
C72 C73 1.536(5) . ?
C72 H72A 0.9800 . ?
C72 H72B 0.9800 . ?
C72 H72C 0.9800 . ?
C73 C74 1.566(5) . ?
C74 C75 1.533(5) . ?
C74 H74A 0.9900 . ?
C74 H74B 0.9900 . ?
C75 C76 1.535(5) . ?
C75 C83 1.545(5) . ?
C76 C77 1.557(5) . ?
C76 H76A 0.9900 . ?
C76 H76B 0.9900 . ?
C77 C78 1.528(5) . ?
C77 C88 1.541(5) . ?
C78 H78A 0.9800 . ?
C78 H78B 0.9800 . ?
C78 H78C 0.9800 . ?
C79 C80 1.380(5) . ?
C79 H79 0.9500 . ?
C80 C81 1.385(5) . ?
C80 H80 0.9500 . ?
C81 C82 1.396(5) . ?
C81 H81 0.9500 . ?
C82 C83 1.383(5) . ?
C82 H82 0.9500 . ?
C84 C85 1.383(5) . ?
C84 H84 0.9500 . ?
C85 C86 1.383(6) . ?
C85 H85 0.9500 . ?
C86 C87 1.391(5) . ?
C86 H86 0.9500 . ?
C87 C88 1.382(5) . ?
C87 H87 0.9500 . ?
Cl1 C89 1.767(4) . ?
Cl2 C89 1.771(4) . ?
C89 H89A 0.9900 . ?
C89 H89B 0.9900 . ?
Cl3 C90 1.766(4) . ?
Cl4 C90 1.759(4) . ?
C90 H90A 0.9900 . ?
C90 H90B 0.9900 . ?

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
O4 Mn1 O1 99.21(10) . . ?
O4 Mn1 O5 91.19(10) . . ?
O1 Mn1 O5 168.90(10) . . ?
O4 Mn1 O2 169.65(9) . . ?
O1 Mn1 O2 90.52(10) . . ?
O5 Mn1 O2 79.35(9) . . ?
O4 Mn1 N1 93.92(10) . . ?
O1 Mn1 N1 77.05(10) . . ?
O5 Mn1 N1 98.53(9) . . ?
O2 Mn1 N1 91.65(10) . . ?
O4 Mn1 N4 75.80(10) . . ?
O1 Mn1 N4 93.72(9) . . ?
O5 Mn1 N4 92.56(9) . . ?
O2 Mn1 N4 100.22(10) . . ?
N1 Mn1 N4 165.08(10) . . ?
O4 Mn1 Mn2 130.82(7) . . ?
O1 Mn1 Mn2 129.96(8) . . ?
O5 Mn1 Mn2 39.71(7) . . ?
O2 Mn1 Mn2 39.65(6) . . ?
N1 Mn1 Mn2 96.09(7) . . ?
N4 Mn1 Mn2 98.82(7) . . ?
O6 Mn2 O3 95.76(10) . . ?
O6 Mn2 O2 167.75(10) . . ?
O3 Mn2 O2 93.67(10) . . ?
O6 Mn2 O5 92.48(10) . . ?
O3 Mn2 O5 169.01(10) . . ?
O2 Mn2 O5 79.26(9) . . ?
O6 Mn2 N2 97.04(10) . . ?
O3 Mn2 N2 90.60(10) . . ?
O2 Mn2 N2 75.01(9) . . ?
O5 Mn2 N2 95.61(10) . . ?
O6 Mn2 N5 92.72(9) . . ?
O3 Mn2 N5 97.53(10) . . ?
O2 Mn2 N5 93.78(9) . . ?
O5 Mn2 N5 74.77(10) . . ?
N2 Mn2 N5 166.61(10) . . ?
O6 Mn2 Mn1 131.22(8) . . ?
O3 Mn2 Mn1 133.01(7) . . ?
O2 Mn2 Mn1 39.79(7) . . ?
O5 Mn2 Mn1 39.47(6) . . ?
N2 Mn2 Mn1 83.55(7) . . ?
N5 Mn2 Mn1 83.12(7) . . ?
C7 O1 Mn1 113.30(18) . . ?
C9 O2 Mn2 113.70(19) . . ?
C9 O2 Mn1 126.3(2) . . ?
Mn2 O2 Mn1 100.56(10) . . ?
C11 O3 Mn2 128.3(2) . . ?
C29 O4 Mn1 114.26(19) . . ?
C31 O5 Mn1 125.58(18) . . ?
C31 O5 Mn2 113.86(19) . . ?
Mn1 O5 Mn2 100.82(10) . . ?
C33 O6 Mn2 127.43(19) . . ?
C1 N1 C5 119.3(3) . . ?
C1 N1 Mn1 132.5(2) . . ?
C5 N1 Mn1 108.1(2) . . ?
C13 N2 C17 119.1(3) . . ?
C13 N2 Mn2 130.3(2) . . ?
C17 N2 Mn2 109.1(2) . . ?
C18 N3 C22 117.1(3) . . ?
C23 N4 C27 118.2(3) . . ?
C23 N4 Mn1 133.8(2) . . ?
C27 N4 Mn1 107.9(2) . . ?
C35 N5 C39 119.7(3) . . ?
C35 N5 Mn2 129.7(2) . . ?
C39 N5 Mn2 109.2(2) . . ?
C40 N6 C44 117.3(3) . . ?
N1 C1 C2 122.8(3) . . ?
N1 C1 H1 118.6 . . ?
C2 C1 H1 118.6 . . ?
C1 C2 C3 118.4(3) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 H2 120.8 . . ?
C2 C3 C4 119.2(3) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C5 C4 C3 119.3(3) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
N1 C5 C4 120.9(3) . . ?
N1 C5 C7 113.0(3) . . ?
C4 C5 C7 126.1(3) . . ?
C7 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C7 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O1 C7 C5 108.6(3) . . ?
O1 C7 C6 106.9(3) . . ?
C5 C7 C6 110.9(3) . . ?
O1 C7 C8 110.8(3) . . ?
C5 C7 C8 111.0(3) . . ?
C6 C7 C8 108.5(3) . . ?
C9 C8 C7 117.8(3) . . ?
C9 C8 H8A 107.9 . . ?
C7 C8 H8A 107.9 . . ?
C9 C8 H8B 107.9 . . ?
C7 C8 H8B 107.9 . . ?
H8A C8 H8B 107.2 . . ?
O2 C9 C8 109.3(3) . . ?
O2 C9 C17 109.1(3) . . ?
C8 C9 C17 112.9(3) . . ?
O2 C9 C10 105.6(3) . . ?
C8 C9 C10 110.2(3) . . ?
C17 C9 C10 109.4(3) . . ?
C9 C10 C11 117.2(3) . . ?
C9 C10 H10A 108.0 . . ?
C11 C10 H10A 108.0 . . ?
C9 C10 H10B 108.0 . . ?
C11 C10 H10B 108.0 . . ?
H10A C10 H10B 107.2 . . ?
O3 C11 C22 110.3(3) . . ?
O3 C11 C12 107.1(3) . . ?
C22 C11 C12 107.7(3) . . ?
O3 C11 C10 114.0(3) . . ?
C22 C11 C10 110.3(3) . . ?
C12 C11 C10 107.1(3) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C13 C14 123.1(3) . . ?
N2 C13 H13 118.5 . . ?
C14 C13 H13 118.5 . . ?
C13 C14 C15 117.7(3) . . ?
C13 C14 H14 121.1 . . ?
C15 C14 H14 121.1 . . ?
C16 C15 C14 120.1(3) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C17 118.4(3) . . ?
C15 C16 H16 120.8 . . ?
C17 C16 H16 120.8 . . ?
N2 C17 C16 121.5(3) . . ?
N2 C17 C9 114.1(3) . . ?
C16 C17 C9 124.3(3) . . ?
N3 C18 C19 124.1(3) . . ?
N3 C18 H18 117.9 . . ?
C19 C18 H18 117.9 . . ?
C18 C19 C20 118.5(4) . . ?
C18 C19 H19 120.7 . . ?
C20 C19 H19 120.7 . . ?
C19 C20 C21 118.6(4) . . ?
C19 C20 H20 120.7 . . ?
C21 C20 H20 120.7 . . ?
C22 C21 C20 119.4(3) . . ?
C22 C21 H21 120.3 . . ?
C20 C21 H21 120.3 . . ?
N3 C22 C21 122.2(3) . . ?
N3 C22 C11 115.2(3) . . ?
C21 C22 C11 122.6(3) . . ?
N4 C23 C24 123.5(4) . . ?
N4 C23 H23 118.2 . . ?
C24 C23 H23 118.2 . . ?
C23 C24 C25 118.0(4) . . ?
C23 C24 H24 121.0 . . ?
C25 C24 H24 121.0 . . ?
C24 C25 C26 119.7(3) . . ?
C24 C25 H25 120.1 . . ?
C26 C25 H25 120.1 . . ?
C25 C26 C27 118.6(3) . . ?
C25 C26 H26 120.7 . . ?
C27 C26 H26 120.7 . . ?
N4 C27 C26 121.9(3) . . ?
N4 C27 C29 112.5(3) . . ?
C26 C27 C29 125.6(3) . . ?
C29 C28 H28A 109.5 . . ?
C29 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C29 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
O4 C29 C28 107.5(3) . . ?
O4 C29 C27 108.2(3) . . ?
C28 C29 C27 112.3(3) . . ?
O4 C29 C30 111.3(3) . . ?
C28 C29 C30 107.4(3) . . ?
C27 C29 C30 110.1(3) . . ?
C31 C30 C29 118.8(3) . . ?
C31 C30 H30A 107.6 . . ?
C29 C30 H30A 107.6 . . ?
C31 C30 H30B 107.6 . . ?
C29 C30 H30B 107.6 . . ?
H30A C30 H30B 107.0 . . ?
O5 C31 C39 109.0(3) . . ?
O5 C31 C30 108.7(2) . . ?
C39 C31 C30 114.4(3) . . ?
O5 C31 C32 106.1(2) . . ?
C39 C31 C32 109.6(3) . . ?
C30 C31 C32 108.6(3) . . ?
C31 C32 C33 117.5(3) . . ?
C31 C32 H32A 107.9 . . ?
C33 C32 H32A 107.9 . . ?
C31 C32 H32B 107.9 . . ?
C33 C32 H32B 107.9 . . ?
H32A C32 H32B 107.2 . . ?
O6 C33 C44 109.8(3) . . ?
O6 C33 C34 106.7(3) . . ?
C44 C33 C34 107.2(3) . . ?
O6 C33 C32 114.8(3) . . ?
C44 C33 C32 111.2(3) . . ?
C34 C33 C32 106.7(3) . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
N5 C35 C36 122.4(3) . . ?
N5 C35 H35 118.8 . . ?
C36 C35 H35 118.8 . . ?
C37 C36 C35 118.1(3) . . ?
C37 C36 H36 120.9 . . ?
C35 C36 H36 120.9 . . ?
C36 C37 C38 119.6(3) . . ?
C36 C37 H37 120.2 . . ?
C38 C37 H37 120.2 . . ?
C39 C38 C37 119.1(3) . . ?
C39 C38 H38 120.4 . . ?
C37 C38 H38 120.4 . . ?
N5 C39 C38 121.0(3) . . ?
N5 C39 C31 114.3(3) . . ?
C38 C39 C31 124.6(3) . . ?
N6 C40 C41 124.6(4) . . ?
N6 C40 H40 117.7 . . ?
C41 C40 H40 117.7 . . ?
C40 C41 C42 117.6(3) . . ?
C40 C41 H41 121.2 . . ?
C42 C41 H41 121.2 . . ?
C41 C42 C43 119.0(4) . . ?
C41 C42 H42 120.5 . . ?
C43 C42 H42 120.5 . . ?
C44 C43 C42 119.3(3) . . ?
C44 C43 H43 120.4 . . ?
C42 C43 H43 120.4 . . ?
N6 C44 C43 122.2(3) . . ?
N6 C44 C33 116.2(3) . . ?
C43 C44 C33 121.6(3) . . ?
O10 Mn3 O7 96.33(11) . . ?
O10 Mn3 O8 168.34(10) . . ?
O7 Mn3 O8 92.26(10) . . ?
O10 Mn3 O11 93.07(10) . . ?
O7 Mn3 O11 166.93(10) . . ?
O8 Mn3 O11 79.80(10) . . ?
O10 Mn3 N11 92.59(10) . . ?
O7 Mn3 N11 95.88(10) . . ?
O8 Mn3 N11 94.35(10) . . ?
O11 Mn3 N11 74.58(10) . . ?
O10 Mn3 N8 96.38(11) . . ?
O7 Mn3 N8 92.44(10) . . ?
O8 Mn3 N8 75.34(10) . . ?
O11 Mn3 N8 95.53(10) . . ?
N11 Mn3 N8 167.01(11) . . ?
O10 Mn3 Mn4 132.64(8) . . ?
O7 Mn3 Mn4 131.01(8) . . ?
O8 Mn3 Mn4 39.67(7) . . ?
O11 Mn3 Mn4 40.14(7) . . ?
N11 Mn3 Mn4 82.54(7) . . ?
N8 Mn3 Mn4 84.47(7) . . ?
O9 Mn4 O12 99.21(10) . . ?
O9 Mn4 O8 90.54(10) . . ?
O12 Mn4 O8 169.88(10) . . ?
O9 Mn4 O11 169.58(10) . . ?
O12 Mn4 O11 90.60(10) . . ?
O8 Mn4 O11 79.85(9) . . ?
O9 Mn4 N9 76.18(10) . . ?
O12 Mn4 N9 92.25(10) . . ?
O8 Mn4 N9 92.72(9) . . ?
O11 Mn4 N9 100.09(10) . . ?
O9 Mn4 N12 94.23(10) . . ?
O12 Mn4 N12 76.94(10) . . ?
O8 Mn4 N12 99.77(10) . . ?
O11 Mn4 N12 91.38(10) . . ?
N9 Mn4 N12 164.38(10) . . ?
O9 Mn4 Mn3 130.20(7) . . ?
O12 Mn4 Mn3 130.59(8) . . ?
O8 Mn4 Mn3 39.74(7) . . ?
O11 Mn4 Mn3 40.11(7) . . ?
N9 Mn4 Mn3 98.75(7) . . ?
N12 Mn4 Mn3 96.86(7) . . ?
C51 O7 Mn3 128.3(2) . . ?
C53 O8 Mn4 126.50(19) . . ?
C53 O8 Mn3 113.94(19) . . ?
Mn4 O8 Mn3 100.59(10) . . ?
C55 O9 Mn4 113.8(2) . . ?
C73 O10 Mn3 127.5(2) . . ?
C75 O11 Mn3 113.96(19) . . ?
C75 O11 Mn4 125.9(2) . . ?
Mn3 O11 Mn4 99.75(10) . . ?
C77 O12 Mn4 113.56(19) . . ?
C49 N7 C45 118.3(3) . . ?
C61 N8 C57 119.1(3) . . ?
C61 N8 Mn3 109.5(2) . . ?
C57 N8 Mn3 129.8(2) . . ?
C62 N9 C66 119.5(3) . . ?
C62 N9 Mn4 132.2(2) . . ?
C66 N9 Mn4 108.3(2) . . ?
C71 N10 C67 117.5(4) . . ?
C79 N11 C83 119.1(3) . . ?
C79 N11 Mn3 129.5(2) . . ?
C83 N11 Mn3 109.9(2) . . ?
C84 N12 C88 118.7(3) . . ?
C84 N12 Mn4 133.0(2) . . ?
C88 N12 Mn4 107.8(2) . . ?
C46 C45 N7 119.4(4) . . ?
C46 C45 H45 120.3 . . ?
N7 C45 H45 120.3 . . ?
C47 C46 C45 117.8(4) . . ?
C47 C46 H46 121.1 . . ?
C45 C46 H46 121.1 . . ?
C48 C47 C46 124.6(4) . . ?
C48 C47 H47 117.7 . . ?
C46 C47 H47 117.7 . . ?
C47 C48 C49 118.0(4) . . ?
C47 C48 H48 121.0 . . ?
C49 C48 H48 121.0 . . ?
C48 C49 N7 121.9(3) . . ?
C48 C49 C51 117.1(3) . . ?
N7 C49 C51 120.8(3) . . ?
C51 C50 H50A 109.5 . . ?
C51 C50 H50B 109.5 . . ?
H50A C50 H50B 109.5 . . ?
C51 C50 H50C 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?
O7 C51 C50 106.5(3) . . ?
O7 C51 C49 109.7(3) . . ?
C50 C51 C49 107.1(3) . . ?
O7 C51 C52 115.0(3) . . ?
C50 C51 C52 107.5(3) . . ?
C49 C51 C52 110.6(3) . . ?
C53 C52 C51 118.2(3) . . ?
C53 C52 H52A 107.8 . . ?
C51 C52 H52A 107.8 . . ?
C53 C52 H52B 107.8 . . ?
C51 C52 H52B 107.8 . . ?
H52A C52 H52B 107.1 . . ?
O8 C53 C52 106.4(3) . . ?
O8 C53 C54 108.8(3) . . ?
C52 C53 C54 108.8(3) . . ?
O8 C53 C61 108.5(3) . . ?
C52 C53 C61 109.3(3) . . ?
C54 C53 C61 114.6(3) . . ?
C53 C54 C55 117.8(3) . . ?
C53 C54 H54A 107.9 . . ?
C55 C54 H54A 107.9 . . ?
C53 C54 H54B 107.9 . . ?
C55 C54 H54B 107.9 . . ?
H54A C54 H54B 107.2 . . ?
O9 C55 C66 109.0(3) . . ?
O9 C55 C56 107.5(3) . . ?
C66 C55 C56 111.4(3) . . ?
O9 C55 C54 111.6(3) . . ?
C66 C55 C54 109.7(3) . . ?
C56 C55 C54 107.6(3) . . ?
C55 C56 H56A 109.5 . . ?
C55 C56 H56B 109.5 . . ?
H56A C56 H56B 109.5 . . ?
C55 C56 H56C 109.5 . . ?
H56A C56 H56C 109.5 . . ?
H56B C56 H56C 109.5 . . ?
N8 C57 C58 122.7(3) . . ?
N8 C57 H57 118.6 . . ?
C58 C57 H57 118.6 . . ?
C59 C58 C57 118.1(3) . . ?
C59 C58 H58 121.0 . . ?
C57 C58 H58 121.0 . . ?
C58 C59 C60 119.6(3) . . ?
C58 C59 H59 120.2 . . ?
C60 C59 H59 120.2 . . ?
C59 C60 C61 119.0(3) . . ?
C59 C60 H60 120.5 . . ?
C61 C60 H60 120.5 . . ?
N8 C61 C60 121.5(3) . . ?
N8 C61 C53 114.3(3) . . ?
C60 C61 C53 124.1(3) . . ?
N9 C62 C63 122.5(3) . . ?
N9 C62 H62 118.8 . . ?
C63 C62 H62 118.8 . . ?
C64 C63 C62 117.5(3) . . ?
C64 C63 H63 121.2 . . ?
C62 C63 H63 121.2 . . ?
C63 C64 C65 120.4(3) . . ?
C63 C64 H64 119.8 . . ?
C65 C64 H64 119.8 . . ?
C66 C65 C64 118.1(3) . . ?
C66 C65 H65 120.9 . . ?
C64 C65 H65 120.9 . . ?
N9 C66 C65 121.9(3) . . ?
N9 C66 C55 112.6(3) . . ?
C65 C66 C55 125.4(3) . . ?
N10 C67 C68 124.1(4) . . ?
N10 C67 H67 117.9 . . ?
C68 C67 H67 117.9 . . ?
C67 C68 C69 118.6(4) . . ?
C67 C68 H68 120.7 . . ?
C69 C68 H68 120.7 . . ?
C68 C69 C70 118.5(4) . . ?
C68 C69 H69 120.7 . . ?
C70 C69 H69 120.7 . . ?
C71 C70 C69 119.8(4) . . ?
C71 C70 H70 120.1 . . ?
C69 C70 H70 120.1 . . ?
N10 C71 C70 121.4(4) . . ?
N10 C71 C73 116.5(3) . . ?
C70 C71 C73 121.9(3) . . ?
C73 C72 H72A 109.5 . . ?
C73 C72 H72B 109.5 . . ?
H72A C72 H72B 109.5 . . ?
C73 C72 H72C 109.5 . . ?
H72A C72 H72C 109.5 . . ?
H72B C72 H72C 109.5 . . ?
O10 C73 C71 110.0(3) . . ?
O10 C73 C72 106.5(3) . . ?
C71 C73 C72 107.1(3) . . ?
O10 C73 C74 114.1(3) . . ?
C71 C73 C74 111.0(3) . . ?
C72 C73 C74 107.7(3) . . ?
C75 C74 C73 117.8(3) . . ?
C75 C74 H74A 107.8 . . ?
C73 C74 H74A 107.8 . . ?
C75 C74 H74B 107.8 . . ?
C73 C74 H74B 107.8 . . ?
H74A C74 H74B 107.2 . . ?
O11 C75 C74 106.6(3) . . ?
O11 C75 C76 108.6(3) . . ?
C74 C75 C76 110.7(3) . . ?
O11 C75 C83 108.5(3) . . ?
C74 C75 C83 108.7(3) . . ?
C76 C75 C83 113.4(3) . . ?
C75 C76 C77 118.4(3) . . ?
C75 C76 H76A 107.7 . . ?
C77 C76 H76A 107.7 . . ?
C75 C76 H76B 107.7 . . ?
C77 C76 H76B 107.7 . . ?
H76A C76 H76B 107.1 . . ?
O12 C77 C78 106.2(3) . . ?
O12 C77 C88 108.0(3) . . ?
C78 C77 C88 111.3(3) . . ?
O12 C77 C76 111.5(3) . . ?
C78 C77 C76 108.7(3) . . ?
C88 C77 C76 111.1(3) . . ?
C77 C78 H78A 109.5 . . ?
C77 C78 H78B 109.5 . . ?
H78A C78 H78B 109.5 . . ?
C77 C78 H78C 109.5 . . ?
H78A C78 H78C 109.5 . . ?
H78B C78 H78C 109.5 . . ?
N11 C79 C80 123.4(3) . . ?
N11 C79 H79 118.3 . . ?
C80 C79 H79 118.3 . . ?
C79 C80 C81 117.7(3) . . ?
C79 C80 H80 121.1 . . ?
C81 C80 H80 121.1 . . ?
C80 C81 C82 119.4(3) . . ?
C80 C81 H81 120.3 . . ?
C82 C81 H81 120.3 . . ?
C83 C82 C81 118.7(3) . . ?
C83 C82 H82 120.6 . . ?
C81 C82 H82 120.6 . . ?
N11 C83 C82 121.6(3) . . ?
N11 C83 C75 113.8(3) . . ?
C82 C83 C75 124.6(3) . . ?
N12 C84 C85 123.5(3) . . ?
N12 C84 H84 118.3 . . ?
C85 C84 H84 118.3 . . ?
C86 C85 C84 117.8(4) . . ?
C86 C85 H85 121.1 . . ?
C84 C85 H85 121.1 . . ?
C85 C86 C87 119.6(3) . . ?
C85 C86 H86 120.2 . . ?
C87 C86 H86 120.2 . . ?
C88 C87 C86 119.0(4) . . ?
C88 C87 H87 120.5 . . ?
C86 C87 H87 120.5 . . ?
N12 C88 C87 121.5(3) . . ?
N12 C88 C77 112.5(3) . . ?
C87 C88 C77 126.0(3) . . ?
Cl1 C89 Cl2 111.8(2) . . ?
Cl1 C89 H89A 109.2 . . ?
Cl2 C89 H89A 109.2 . . ?
Cl1 C89 H89B 109.2 . . ?
Cl2 C89 H89B 109.2 . . ?
H89A C89 H89B 107.9 . . ?
Cl4 C90 Cl3 110.8(2) . . ?
Cl4 C90 H90A 109.5 . . ?
Cl3 C90 H90A 109.5 . . ?
Cl4 C90 H90B 109.5 . . ?
Cl3 C90 H90B 109.5 . . ?
H90A C90 H90B 108.1 . . ?

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
O4 Mn1 O1 C7 -129.3(2) . . . . ?
O5 Mn1 O1 C7 30.2(6) . . . . ?
O2 Mn1 O1 C7 54.2(2) . . . . ?
N1 Mn1 O1 C7 -37.4(2) . . . . ?
N4 Mn1 O1 C7 154.5(2) . . . . ?
Mn2 Mn1 O1 C7 49.7(2) . . . . ?
O6 Mn2 O3 C11 145.6(3) . . . . ?
O2 Mn2 O3 C11 -26.5(3) . . . . ?
O5 Mn2 O3 C11 -76.1(6) . . . . ?
N2 Mn2 O3 C11 48.5(3) . . . . ?
N5 Mn2 O3 C11 -120.9(3) . . . . ?
Mn1 Mn2 O3 C11 -33.2(3) . . . . ?
O1 Mn1 O4 C29 -130.3(2) . . . . ?
O5 Mn1 O4 C29 53.5(2) . . . . ?
O2 Mn1 O4 C29 29.7(6) . . . . ?
N1 Mn1 O4 C29 152.2(2) . . . . ?
N4 Mn1 O4 C29 -38.8(2) . . . . ?
Mn2 Mn1 O4 C29 50.7(2) . . . . ?
O3 Mn2 O6 C33 140.9(2) . . . . ?
O2 Mn2 O6 C33 -79.0(5) . . . . ?
O5 Mn2 O6 C33 -31.9(3) . . . . ?
N2 Mn2 O6 C33 -127.8(2) . . . . ?
N5 Mn2 O6 C33 43.0(3) . . . . ?
Mn1 Mn2 O6 C33 -40.2(3) . . . . ?
C5 N1 C1 C2 -2.2(5) . . . . ?
Mn1 N1 C1 C2 173.4(3) . . . . ?
N1 C1 C2 C3 1.9(6) . . . . ?
C1 C2 C3 C4 -0.4(6) . . . . ?
C2 C3 C4 C5 -0.5(6) . . . . ?
C1 N1 C5 C4 1.1(5) . . . . ?
Mn1 N1 C5 C4 -175.5(3) . . . . ?
C1 N1 C5 C7 -179.0(3) . . . . ?
Mn1 N1 C5 C7 4.4(3) . . . . ?
C3 C4 C5 N1 0.2(6) . . . . ?
C3 C4 C5 C7 -179.7(4) . . . . ?
Mn1 O1 C7 C5 51.0(3) . . . . ?
Mn1 O1 C7 C6 170.8(2) . . . . ?
Mn1 O1 C7 C8 -71.1(3) . . . . ?
N1 C5 C7 O1 -32.8(4) . . . . ?
C4 C5 C7 O1 147.1(4) . . . . ?
N1 C5 C7 C6 -150.0(3) . . . . ?
C4 C5 C7 C6 29.9(5) . . . . ?
N1 C5 C7 C8 89.2(3) . . . . ?
C4 C5 C7 C8 -90.9(4) . . . . ?
O1 C7 C8 C9 64.6(4) . . . . ?
C5 C7 C8 C9 -56.1(4) . . . . ?
C6 C7 C8 C9 -178.3(3) . . . . ?
Mn2 O2 C9 C8 168.6(2) . . . . ?
Mn1 O2 C9 C8 43.8(3) . . . . ?
Mn2 O2 C9 C17 44.7(3) . . . . ?
Mn1 O2 C9 C17 -80.1(3) . . . . ?
Mn2 O2 C9 C10 -72.9(3) . . . . ?
Mn1 O2 C9 C10 162.35(19) . . . . ?
C7 C8 C9 O2 -46.7(4) . . . . ?
C7 C8 C9 C17 74.9(4) . . . . ?
C7 C8 C9 C10 -162.3(3) . . . . ?
O2 C9 C10 C11 68.5(3) . . . . ?
C8 C9 C10 C11 -173.5(3) . . . . ?
C17 C9 C10 C11 -48.7(4) . . . . ?
Mn2 O3 C11 C22 -98.5(3) . . . . ?
Mn2 O3 C11 C12 144.5(2) . . . . ?
Mn2 O3 C11 C10 26.2(4) . . . . ?
C9 C10 C11 O3 -42.8(4) . . . . ?
C9 C10 C11 C22 81.9(4) . . . . ?
C9 C10 C11 C12 -161.1(3) . . . . ?
C17 N2 C13 C14 -0.8(5) . . . . ?
Mn2 N2 C13 C14 -164.8(3) . . . . ?
N2 C13 C14 C15 2.6(5) . . . . ?
C13 C14 C15 C16 -1.3(6) . . . . ?
C14 C15 C16 C17 -1.6(6) . . . . ?
C13 N2 C17 C16 -2.3(5) . . . . ?
Mn2 N2 C17 C16 164.8(3) . . . . ?
C13 N2 C17 C9 -179.7(3) . . . . ?
Mn2 N2 C17 C9 -12.6(3) . . . . ?
C15 C16 C17 N2 3.5(5) . . . . ?
C15 C16 C17 C9 -179.4(3) . . . . ?
O2 C9 C17 N2 -17.1(4) . . . . ?
C8 C9 C17 N2 -138.8(3) . . . . ?
C10 C9 C17 N2 98.0(3) . . . . ?
O2 C9 C17 C16 165.6(3) . . . . ?
C8 C9 C17 C16 43.9(5) . . . . ?
C10 C9 C17 C16 -79.3(4) . . . . ?
C22 N3 C18 C19 2.0(6) . . . . ?
N3 C18 C19 C20 -2.6(6) . . . . ?
C18 C19 C20 C21 0.6(6) . . . . ?
C19 C20 C21 C22 1.7(5) . . . . ?
C18 N3 C22 C21 0.5(5) . . . . ?
C18 N3 C22 C11 179.6(3) . . . . ?
C20 C21 C22 N3 -2.3(5) . . . . ?
C20 C21 C22 C11 178.7(3) . . . . ?
O3 C11 C22 N3 -178.7(3) . . . . ?
C12 C11 C22 N3 -62.2(4) . . . . ?
C10 C11 C22 N3 54.4(4) . . . . ?
O3 C11 C22 C21 0.3(5) . . . . ?
C12 C11 C22 C21 116.9(4) . . . . ?
C10 C11 C22 C21 -126.5(3) . . . . ?
C27 N4 C23 C24 -0.5(5) . . . . ?
Mn1 N4 C23 C24 175.1(3) . . . . ?
N4 C23 C24 C25 0.9(5) . . . . ?
C23 C24 C25 C26 0.2(5) . . . . ?
C24 C25 C26 C27 -1.8(5) . . . . ?
C23 N4 C27 C26 -1.2(5) . . . . ?
Mn1 N4 C27 C26 -177.8(3) . . . . ?
C23 N4 C27 C29 -178.8(3) . . . . ?
Mn1 N4 C27 C29 4.5(3) . . . . ?
C25 C26 C27 N4 2.3(5) . . . . ?
C25 C26 C27 C29 179.6(3) . . . . ?
Mn1 O4 C29 C28 174.8(2) . . . . ?
Mn1 O4 C29 C27 53.3(3) . . . . ?
Mn1 O4 C29 C30 -67.8(3) . . . . ?
N4 C27 C29 O4 -33.4(4) . . . . ?
C26 C27 C29 O4 149.1(3) . . . . ?
N4 C27 C29 C28 -151.9(3) . . . . ?
C26 C27 C29 C28 30.5(5) . . . . ?
N4 C27 C29 C30 88.4(3) . . . . ?
C26 C27 C29 C30 -89.1(4) . . . . ?
O4 C29 C30 C31 62.0(4) . . . . ?
C28 C29 C30 C31 179.5(3) . . . . ?
C27 C29 C30 C31 -57.9(4) . . . . ?
Mn1 O5 C31 C39 -79.1(3) . . . . ?
Mn2 O5 C31 C39 45.5(3) . . . . ?
Mn1 O5 C31 C30 46.2(3) . . . . ?
Mn2 O5 C31 C30 170.86(18) . . . . ?
Mn1 O5 C31 C32 162.9(2) . . . . ?
Mn2 O5 C31 C32 -72.5(3) . . . . ?
C29 C30 C31 O5 -47.3(4) . . . . ?
C29 C30 C31 C39 74.8(4) . . . . ?
C29 C30 C31 C32 -162.4(3) . . . . ?
O5 C31 C32 C33 65.3(3) . . . . ?
C39 C31 C32 C33 -52.3(4) . . . . ?
C30 C31 C32 C33 -178.0(3) . . . . ?
Mn2 O6 C33 C44 -95.5(3) . . . . ?
Mn2 O6 C33 C34 148.6(2) . . . . ?
Mn2 O6 C33 C32 30.7(4) . . . . ?
C31 C32 C33 O6 -42.4(4) . . . . ?
C31 C32 C33 C44 83.1(3) . . . . ?
C31 C32 C33 C34 -160.3(3) . . . . ?
C39 N5 C35 C36 0.0(5) . . . . ?
Mn2 N5 C35 C36 -165.1(2) . . . . ?
N5 C35 C36 C37 1.3(5) . . . . ?
C35 C36 C37 C38 -0.9(5) . . . . ?
C36 C37 C38 C39 -0.6(5) . . . . ?
C35 N5 C39 C38 -1.7(4) . . . . ?
Mn2 N5 C39 C38 166.2(2) . . . . ?
C35 N5 C39 C31 -178.2(3) . . . . ?
Mn2 N5 C39 C31 -10.3(3) . . . . ?
C37 C38 C39 N5 2.0(5) . . . . ?
C37 C38 C39 C31 178.2(3) . . . . ?
O5 C31 C39 N5 -19.1(3) . . . . ?
C30 C31 C39 N5 -141.0(3) . . . . ?
C32 C31 C39 N5 96.7(3) . . . . ?
O5 C31 C39 C38 164.5(3) . . . . ?
C30 C31 C39 C38 42.6(4) . . . . ?
C32 C31 C39 C38 -79.7(4) . . . . ?
C44 N6 C40 C41 -1.3(6) . . . . ?
N6 C40 C41 C42 0.9(6) . . . . ?
C40 C41 C42 C43 0.1(6) . . . . ?
C41 C42 C43 C44 -0.5(5) . . . . ?
C40 N6 C44 C43 0.8(5) . . . . ?
C40 N6 C44 C33 178.1(3) . . . . ?
C42 C43 C44 N6 0.1(5) . . . . ?
C42 C43 C44 C33 -177.1(3) . . . . ?
O6 C33 C44 N6 179.6(3) . . . . ?
C34 C33 C44 N6 -64.9(4) . . . . ?
C32 C33 C44 N6 51.4(4) . . . . ?
O6 C33 C44 C43 -3.1(4) . . . . ?
C34 C33 C44 C43 112.4(3) . . . . ?
C32 C33 C44 C43 -131.3(3) . . . . ?
O10 Mn3 O7 C51 141.8(3) . . . . ?
O8 Mn3 O7 C51 -30.3(3) . . . . ?
O11 Mn3 O7 C51 -82.5(5) . . . . ?
N11 Mn3 O7 C51 -124.9(3) . . . . ?
N8 Mn3 O7 C51 45.1(3) . . . . ?
Mn4 Mn3 O7 C51 -39.7(3) . . . . ?
O12 Mn4 O9 C55 -128.5(2) . . . . ?
O8 Mn4 O9 C55 54.3(2) . . . . ?
O11 Mn4 O9 C55 31.7(6) . . . . ?
N9 Mn4 O9 C55 -38.4(2) . . . . ?
N12 Mn4 O9 C55 154.1(2) . . . . ?
Mn3 Mn4 O9 C55 51.5(2) . . . . ?
O7 Mn3 O10 C73 138.9(3) . . . . ?
O8 Mn3 O10 C73 -83.9(6) . . . . ?
O11 Mn3 O10 C73 -32.0(3) . . . . ?
N11 Mn3 O10 C73 42.6(3) . . . . ?
N8 Mn3 O10 C73 -128.0(3) . . . . ?
Mn4 Mn3 O10 C73 -39.6(3) . . . . ?
O9 Mn4 O12 C77 -129.5(2) . . . . ?
O8 Mn4 O12 C77 34.8(7) . . . . ?
O11 Mn4 O12 C77 54.0(2) . . . . ?
N9 Mn4 O12 C77 154.2(2) . . . . ?
N12 Mn4 O12 C77 -37.2(2) . . . . ?
Mn3 Mn4 O12 C77 50.6(3) . . . . ?
C49 N7 C45 C46 1.5(6) . . . . ?
N7 C45 C46 C47 -0.9(6) . . . . ?
C45 C46 C47 C48 -0.1(7) . . . . ?
C46 C47 C48 C49 0.5(7) . . . . ?
C47 C48 C49 N7 0.1(6) . . . . ?
C47 C48 C49 C51 175.6(3) . . . . ?
C45 N7 C49 C48 -1.1(5) . . . . ?
C45 N7 C49 C51 -176.4(3) . . . . ?
Mn3 O7 C51 C50 146.2(2) . . . . ?
Mn3 O7 C51 C49 -98.2(3) . . . . ?
Mn3 O7 C51 C52 27.2(4) . . . . ?
C48 C49 C51 O7 -174.0(3) . . . . ?
N7 C49 C51 O7 1.5(4) . . . . ?
C48 C49 C51 C50 -58.8(4) . . . . ?
N7 C49 C51 C50 116.7(4) . . . . ?
C48 C49 C51 C52 58.1(4) . . . . ?
N7 C49 C51 C52 -126.4(3) . . . . ?
O7 C51 C52 C53 -38.9(4) . . . . ?
C50 C51 C52 C53 -157.3(3) . . . . ?
C49 C51 C52 C53 86.0(4) . . . . ?
Mn4 O8 C53 C52 161.9(2) . . . . ?
Mn3 O8 C53 C52 -72.7(3) . . . . ?
Mn4 O8 C53 C54 44.8(3) . . . . ?
Mn3 O8 C53 C54 170.16(19) . . . . ?
Mn4 O8 C53 C61 -80.5(3) . . . . ?
Mn3 O8 C53 C61 44.8(3) . . . . ?
C51 C52 C53 O8 63.6(4) . . . . ?
C51 C52 C53 C54 -179.3(3) . . . . ?
C51 C52 C53 C61 -53.4(4) . . . . ?
O8 C53 C54 C55 -45.8(4) . . . . ?
C52 C53 C54 C55 -161.3(3) . . . . ?
C61 C53 C54 C55 75.9(4) . . . . ?
Mn4 O9 C55 C66 51.2(3) . . . . ?
Mn4 O9 C55 C56 172.1(2) . . . . ?
Mn4 O9 C55 C54 -70.1(3) . . . . ?
C53 C54 C55 O9 62.7(4) . . . . ?
C53 C54 C55 C66 -58.2(4) . . . . ?
C53 C54 C55 C56 -179.6(3) . . . . ?
C61 N8 C57 C58 -0.7(5) . . . . ?
Mn3 N8 C57 C58 -164.8(3) . . . . ?
N8 C57 C58 C59 1.7(5) . . . . ?
C57 C58 C59 C60 -1.7(6) . . . . ?
C58 C59 C60 C61 0.7(6) . . . . ?
C57 N8 C61 C60 -0.3(5) . . . . ?
Mn3 N8 C61 C60 166.8(3) . . . . ?
C57 N8 C61 C53 -177.2(3) . . . . ?
Mn3 N8 C61 C53 -10.1(3) . . . . ?
C59 C60 C61 N8 0.2(5) . . . . ?
C59 C60 C61 C53 176.9(3) . . . . ?
O8 C53 C61 N8 -18.9(4) . . . . ?
C52 C53 C61 N8 96.7(3) . . . . ?
C54 C53 C61 N8 -140.7(3) . . . . ?
O8 C53 C61 C60 164.2(3) . . . . ?
C52 C53 C61 C60 -80.1(4) . . . . ?
C54 C53 C61 C60 42.4(4) . . . . ?
C66 N9 C62 C63 -1.0(5) . . . . ?
Mn4 N9 C62 C63 177.4(2) . . . . ?
N9 C62 C63 C64 1.9(5) . . . . ?
C62 C63 C64 C65 -0.4(5) . . . . ?
C63 C64 C65 C66 -1.8(5) . . . . ?
C62 N9 C66 C65 -1.4(5) . . . . ?
Mn4 N9 C66 C65 179.9(3) . . . . ?
C62 N9 C66 C55 -179.7(3) . . . . ?
Mn4 N9 C66 C55 1.6(3) . . . . ?
C64 C65 C66 N9 2.7(5) . . . . ?
C64 C65 C66 C55 -179.2(3) . . . . ?
O9 C55 C66 N9 -30.4(4) . . . . ?
C56 C55 C66 N9 -148.9(3) . . . . ?
C54 C55 C66 N9 92.1(3) . . . . ?
O9 C55 C66 C65 151.4(3) . . . . ?
C56 C55 C66 C65 32.9(4) . . . . ?
C54 C55 C66 C65 -86.1(4) . . . . ?
C71 N10 C67 C68 0.1(7) . . . . ?
N10 C67 C68 C69 -0.7(7) . . . . ?
C67 C68 C69 C70 -0.1(6) . . . . ?
C68 C69 C70 C71 1.6(6) . . . . ?
C67 N10 C71 C70 1.4(6) . . . . ?
C67 N10 C71 C73 177.5(4) . . . . ?
C69 C70 C71 N10 -2.3(6) . . . . ?
C69 C70 C71 C73 -178.2(3) . . . . ?
Mn3 O10 C73 C71 -94.5(3) . . . . ?
Mn3 O10 C73 C72 149.8(3) . . . . ?
Mn3 O10 C73 C74 31.1(4) . . . . ?
N10 C71 C73 O10 179.9(3) . . . . ?
C70 C71 C73 O10 -4.0(5) . . . . ?
N10 C71 C73 C72 -64.7(4) . . . . ?
C70 C71 C73 C72 111.3(4) . . . . ?
N10 C71 C73 C74 52.6(4) . . . . ?
C70 C71 C73 C74 -131.4(4) . . . . ?
O10 C73 C74 C75 -42.8(4) . . . . ?
C71 C73 C74 C75 82.3(4) . . . . ?
C72 C73 C74 C75 -160.8(3) . . . . ?
Mn3 O11 C75 C74 -71.3(3) . . . . ?
Mn4 O11 C75 C74 165.3(2) . . . . ?
Mn3 O11 C75 C76 169.3(2) . . . . ?
Mn4 O11 C75 C76 45.9(3) . . . . ?
Mn3 O11 C75 C83 45.6(3) . . . . ?
Mn4 O11 C75 C83 -77.8(3) . . . . ?
C73 C74 C75 O11 65.2(4) . . . . ?
C73 C74 C75 C76 -176.9(3) . . . . ?
C73 C74 C75 C83 -51.6(4) . . . . ?
O11 C75 C76 C77 -47.1(4) . . . . ?
C74 C75 C76 C77 -163.8(3) . . . . ?
C83 C75 C76 C77 73.6(4) . . . . ?
Mn4 O12 C77 C78 172.4(2) . . . . ?
Mn4 O12 C77 C88 52.9(3) . . . . ?
Mn4 O12 C77 C76 -69.3(3) . . . . ?
C75 C76 C77 O12 63.1(4) . . . . ?
C75 C76 C77 C78 179.8(3) . . . . ?
C75 C76 C77 C88 -57.4(4) . . . . ?
C83 N11 C79 C80 -1.1(5) . . . . ?
Mn3 N11 C79 C80 -166.0(3) . . . . ?
N11 C79 C80 C81 2.6(6) . . . . ?
C79 C80 C81 C82 -1.7(6) . . . . ?
C80 C81 C82 C83 -0.6(6) . . . . ?
C79 N11 C83 C82 -1.3(5) . . . . ?
Mn3 N11 C83 C82 166.3(3) . . . . ?
C79 N11 C83 C75 -178.8(3) . . . . ?
Mn3 N11 C83 C75 -11.2(3) . . . . ?
C81 C82 C83 N11 2.1(6) . . . . ?
C81 C82 C83 C75 179.3(3) . . . . ?
O11 C75 C83 N11 -18.6(4) . . . . ?
C74 C75 C83 N11 97.0(3) . . . . ?
C76 C75 C83 N11 -139.4(3) . . . . ?
O11 C75 C83 C82 164.0(3) . . . . ?
C74 C75 C83 C82 -80.4(4) . . . . ?
C76 C75 C83 C82 43.3(5) . . . . ?
C88 N12 C84 C85 -1.7(5) . . . . ?
Mn4 N12 C84 C85 168.3(3) . . . . ?
N12 C84 C85 C86 0.6(6) . . . . ?
C84 C85 C86 C87 0.5(6) . . . . ?
C85 C86 C87 C88 -0.6(6) . . . . ?
C84 N12 C88 C87 1.6(5) . . . . ?
Mn4 N12 C88 C87 -170.7(3) . . . . ?
C84 N12 C88 C77 -179.5(3) . . . . ?
Mn4 N12 C88 C77 8.2(3) . . . . ?
C86 C87 C88 N12 -0.5(6) . . . . ?
C86 C87 C88 C77 -179.2(3) . . . . ?
O12 C77 C88 N12 -36.5(4) . . . . ?
C78 C77 C88 N12 -152.7(3) . . . . ?
C76 C77 C88 N12 86.0(3) . . . . ?
O12 C77 C88 C87 142.3(4) . . . . ?
C78 C77 C88 C87 26.1(5) . . . . ?
C76 C77 C88 C87 -95.2(4) . . . . ?

_refine_diff_density_max         0.792
_refine_diff_density_min         -0.736
_refine_diff_density_rms         0.108



