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

data_jp132
_audit_block_doi                 10.5517/ccdc.csd.cc1jyzct
_database_code_depnum_ccdc_archive 'CCDC 1428987'
_audit_update_record             
;
2017-02-24 deposited with the CCDC.
2017-03-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H30 Cd2 N2 O18'
_chemical_formula_weight         931.36

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'
Cd Cd -0.8075 1.2024 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

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

_cell_length_a                   7.4650(3)
_cell_length_b                   10.1512(4)
_cell_length_c                   11.7742(5)
_cell_angle_alpha                104.3926(10)
_cell_angle_beta                 108.4324(10)
_cell_angle_gamma                101.8028(10)
_cell_volume                     780.00(6)
_cell_formula_units_Z            1
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    23527
_cell_measurement_theta_min      2.177
_cell_measurement_theta_max      28.375

_exptl_crystal_description       plates
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.983
_exptl_crystal_F_000             464
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_exptl_absorpt_coefficient_mu    1.455
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.816
_exptl_absorpt_correction_T_max  0.909
_exptl_absorpt_process_details   'SADABS (Sheldrick 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23527
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.177
_diffrn_reflns_theta_max         28.375
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3873
_reflns_number_gt                3838
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX2 (Bruker, 2013)'
_computing_cell_refinement       'APEX2 (Bruker, 2013)'
_computing_data_reduction        'APEX2 (Bruker, 2013)'
_computing_structure_solution    'SHELXT-2014/6 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    Diamond
_computing_publication_material  'SHELXT-2014/6 (Sheldrick, 2014)'
_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0219P)²+1.1340P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3873
_refine_ls_number_parameters     241
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0203
_refine_ls_R_factor_gt           0.0202
_refine_ls_wR_factor_ref         0.0533
_refine_ls_wR_factor_gt          0.0532
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_restrained_S_all      1.109
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cd1 Cd 0.59817(2) 0.84844(2) 0.92788(2) 0.00901(5) Uani 1 1 d . . . . .
O1 O 0.1675(2) 0.26490(14) 0.11704(13) 0.0151(3) Uani 1 1 d . . . . .
O2 O 0.3930(2) 0.37438(14) 0.05839(14) 0.0148(3) Uani 1 1 d . . . . .
O3 O 0.4546(2) 0.88767(16) 0.07529(15) 0.0210(3) Uani 1 1 d . . . . .
O4 O 0.2717(2) 0.99515(15) 0.15565(16) 0.0207(3) Uani 1 1 d . . . . .
O5 O 0.2739(2) 0.78233(16) 0.79646(13) 0.0172(3) Uani 1 1 d . . . . .
O6 O 0.3618(2) 0.6692(2) 0.64527(16) 0.0313(4) Uani 1 1 d . . . . .
N1 N -0.1626(2) 0.64867(16) 0.37015(14) 0.0109(3) Uani 1 1 d . . . . .
C1 C 0.2544(3) 0.37276(19) 0.09880(16) 0.0105(3) Uani 1 1 d . . . . .
C2 C 0.1951(3) 0.50622(18) 0.12891(16) 0.0095(3) Uani 1 1 d . . . . .
C3 C 0.2904(2) 0.63028(18) 0.11321(16) 0.0094(3) Uani 1 1 d . . . . .
H3 H 0.3920 0.6304 0.0809 0.011 Uiso 1 1 calc R U . . .
C4 C 0.2362(3) 0.75395(18) 0.14509(16) 0.0097(3) Uani 1 1 d . . . . .
C5 C 0.3280(3) 0.88686(19) 0.12336(16) 0.0106(3) Uani 1 1 d . . . . .
C6 C 0.0852(3) 0.75226(19) 0.19128(16) 0.0107(3) Uani 1 1 d . . . . .
H6 H 0.0516 0.8373 0.2159 0.013 Uiso 1 1 calc R U . . .
C7 C -0.0165(3) 0.62765(19) 0.20170(16) 0.0098(3) Uani 1 1 d . . . . .
C8 C 0.0396(3) 0.50469(18) 0.17088(16) 0.0103(3) Uani 1 1 d . . . . .
H8 H -0.0285 0.4195 0.1785 0.012 Uiso 1 1 calc R U . . .
C9 C -0.1973(3) 0.6235(2) 0.23288(16) 0.0123(3) Uani 1 1 d . . . . .
H9A H -0.2535 0.6966 0.2069 0.015 Uiso 1 1 calc R U . . .
H9B H -0.2979 0.5289 0.1815 0.015 Uiso 1 1 calc R U . . .
C10 C 0.0146(3) 0.66760(19) 0.45876(17) 0.0117(3) Uani 1 1 d . . . . .
H10 H 0.1241 0.6634 0.4349 0.014 Uiso 1 1 calc R U . . .
C11 C 0.0393(3) 0.69331(19) 0.58508(17) 0.0124(3) Uani 1 1 d . . . . .
C12 C -0.1230(3) 0.6985(2) 0.61824(18) 0.0156(3) Uani 1 1 d . . . . .
H12 H -0.1088 0.7173 0.7043 0.019 Uiso 1 1 calc R U . . .
C13 C -0.3065(3) 0.6759(2) 0.52413(19) 0.0202(4) Uani 1 1 d . . . . .
H13 H -0.4193 0.6772 0.5450 0.024 Uiso 1 1 calc R U . . .
C14 C -0.3220(3) 0.6518(2) 0.40122(19) 0.0177(4) Uani 1 1 d . . . . .
H14 H -0.4465 0.6371 0.3367 0.021 Uiso 1 1 calc R U . . .
C15 C 0.2433(3) 0.7166(2) 0.68191(18) 0.0135(3) Uani 1 1 d . . . . .
O1W O 0.8650(2) 0.99451(15) 1.12473(14) 0.0183(3) Uani 1 1 d . . . . .
H1WA H 0.8353 1.0705 1.1414 0.022 Uiso 1 1 d R U . . .
H1WB H 0.9745 1.0064 1.1168 0.022 Uiso 1 1 d R U . . .
O2W O 0.1545(6) 1.0431(3) 0.6187(3) 0.0940(12) Uani 1 1 d G . . . .
H2WA H 0.2370 1.0345 0.5849 0.141 Uiso 1 1 d R U . . .
H2WB H 0.1812 1.0142 0.6812 0.141 Uiso 1 1 d R U . . .
O3W O 0.4279(5) 0.9351(4) 0.5657(3) 0.0851(10) Uani 1 1 d G . . A -1
H3WA H 0.4667 0.9531 0.5100 0.128 Uiso 1 1 d R U . A -1
H3WB H 0.5257 0.9400 0.6284 0.128 Uiso 1 1 d R U . A -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
Cd1 O5 2.2706(14) . ?
Cd1 O4 2.2761(14) 2_676 ?
Cd1 O3 2.3082(14) 1_556 ?
Cd1 O2 2.3201(13) 2_666 ?
Cd1 O1W 2.3879(14) . ?
Cd1 O1 2.4017(14) 2_666 ?
Cd1 C1 2.6892(17) 2_666 ?
O1 C1 1.257(2) . ?
O1 Cd1 2.4017(13) 2_666 ?
O2 C1 1.267(2) . ?
O2 Cd1 2.3201(13) 2_666 ?
O3 C5 1.245(2) . ?
O3 Cd1 2.3082(14) 1_554 ?
O4 C5 1.269(2) . ?
O4 Cd1 2.2761(14) 2_676 ?
O5 C15 1.270(2) . ?
O6 C15 1.230(2) . ?
N1 C10 1.341(2) . ?
N1 C14 1.355(2) . ?
N1 C9 1.499(2) . ?
C1 C2 1.504(2) . ?
C1 Cd1 2.6892(17) 2_666 ?
C2 C8 1.397(2) . ?
C2 C3 1.400(2) . ?
C3 C4 1.397(2) . ?
C3 H3 0.9500 . ?
C4 C6 1.396(2) . ?
C4 C5 1.503(2) . ?
C6 C7 1.391(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.396(2) . ?
C7 C9 1.502(2) . ?
C8 H8 0.9500 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.389(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.392(3) . ?
C11 C15 1.515(2) . ?
C12 C13 1.394(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.369(3) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
O1W H1WA 0.8402 . ?
O1W H1WB 0.8400 . ?
O2W H2WA 0.8400 . ?
O2W H2WB 0.8399 . ?
O3W H3WA 0.8400 . ?
O3W H3WB 0.8400 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O5 Cd1 O4 98.98(6) . 2_676 ?
O5 Cd1 O3 79.68(5) . 1_556 ?
O4 Cd1 O3 128.92(5) 2_676 1_556 ?
O5 Cd1 O2 97.53(5) . 2_666 ?
O4 Cd1 O2 137.67(5) 2_676 2_666 ?
O3 Cd1 O2 92.29(5) 1_556 2_666 ?
O5 Cd1 O1W 149.90(5) . . ?
O4 Cd1 O1W 85.53(6) 2_676 . ?
O3 Cd1 O1W 74.60(5) 1_556 . ?
O2 Cd1 O1W 98.85(5) 2_666 . ?
O5 Cd1 O1 124.04(5) . 2_666 ?
O4 Cd1 O1 82.79(5) 2_676 2_666 ?
O3 Cd1 O1 139.83(5) 1_556 2_666 ?
O2 Cd1 O1 55.85(5) 2_666 2_666 ?
O1W Cd1 O1 86.00(5) . 2_666 ?
O5 Cd1 C1 111.63(5) . 2_666 ?
O4 Cd1 C1 109.92(5) 2_676 2_666 ?
O3 Cd1 C1 117.98(6) 1_556 2_666 ?
O2 Cd1 C1 28.09(5) 2_666 2_666 ?
O1W Cd1 C1 94.31(5) . 2_666 ?
O1 Cd1 C1 27.86(5) 2_666 2_666 ?
C1 O1 Cd1 88.90(11) . 2_666 ?
C1 O2 Cd1 92.37(11) . 2_666 ?
C5 O3 Cd1 161.47(14) . 1_554 ?
C5 O4 Cd1 105.10(12) . 2_676 ?
C15 O5 Cd1 112.42(12) . . ?
C10 N1 C14 120.95(16) . . ?
C10 N1 C9 122.95(15) . . ?
C14 N1 C9 116.11(15) . . ?
O1 C1 O2 122.48(16) . . ?
O1 C1 C2 118.86(16) . . ?
O2 C1 C2 118.64(16) . . ?
O1 C1 Cd1 63.24(9) . 2_666 ?
O2 C1 Cd1 59.54(9) . 2_666 ?
C2 C1 Cd1 172.74(12) . 2_666 ?
C8 C2 C3 119.77(16) . . ?
C8 C2 C1 119.13(16) . . ?
C3 C2 C1 121.10(16) . . ?
C4 C3 C2 119.96(16) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C6 C4 C3 119.57(16) . . ?
C6 C4 C5 118.88(15) . . ?
C3 C4 C5 121.44(15) . . ?
O3 C5 O4 122.51(17) . . ?
O3 C5 C4 119.84(16) . . ?
O4 C5 C4 117.65(16) . . ?
C7 C6 C4 120.83(16) . . ?
C7 C6 H6 119.6 . . ?
C4 C6 H6 119.6 . . ?
C6 C7 C8 119.35(16) . . ?
C6 C7 C9 119.37(16) . . ?
C8 C7 C9 120.98(16) . . ?
C7 C8 C2 120.42(16) . . ?
C7 C8 H8 119.8 . . ?
C2 C8 H8 119.8 . . ?
N1 C9 C7 115.21(14) . . ?
N1 C9 H9A 108.5 . . ?
C7 C9 H9A 108.5 . . ?
N1 C9 H9B 108.5 . . ?
C7 C9 H9B 108.5 . . ?
H9A C9 H9B 107.5 . . ?
N1 C10 C11 120.52(16) . . ?
N1 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C10 C11 C12 118.96(17) . . ?
C10 C11 C15 118.49(16) . . ?
C12 C11 C15 122.54(16) . . ?
C11 C12 C13 119.47(17) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
C14 C13 C12 119.07(18) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
N1 C14 C13 121.01(18) . . ?
N1 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
O6 C15 O5 125.77(18) . . ?
O6 C15 C11 118.87(17) . . ?
O5 C15 C11 115.35(16) . . ?
Cd1 O1W H1WA 102.4 . . ?
Cd1 O1W H1WB 111.0 . . ?
H1WA O1W H1WB 113.0 . . ?
H2WA O2W H2WB 109.5 . . ?
H3WA O3W H3WB 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
Cd1 O1 C1 O2 6.39(17) 2_666 . . . ?
Cd1 O1 C1 C2 -172.14(14) 2_666 . . . ?
Cd1 O2 C1 O1 -6.62(18) 2_666 . . . ?
Cd1 O2 C1 C2 171.92(13) 2_666 . . . ?
O1 C1 C2 C8 -2.8(2) . . . . ?
O2 C1 C2 C8 178.62(16) . . . . ?
O1 C1 C2 C3 178.44(16) . . . . ?
O2 C1 C2 C3 -0.1(2) . . . . ?
C8 C2 C3 C4 3.0(2) . . . . ?
C1 C2 C3 C4 -178.28(15) . . . . ?
C2 C3 C4 C6 -0.7(2) . . . . ?
C2 C3 C4 C5 -176.87(15) . . . . ?
Cd1 O3 C5 O4 -103.1(4) 1_554 . . . ?
Cd1 O3 C5 C4 77.0(5) 1_554 . . . ?
Cd1 O4 C5 O3 10.5(2) 2_676 . . . ?
Cd1 O4 C5 C4 -169.56(12) 2_676 . . . ?
C6 C4 C5 O3 -175.82(17) . . . . ?
C3 C4 C5 O3 0.4(3) . . . . ?
C6 C4 C5 O4 4.2(2) . . . . ?
C3 C4 C5 O4 -179.54(17) . . . . ?
C3 C4 C6 C7 -2.3(3) . . . . ?
C5 C4 C6 C7 174.01(15) . . . . ?
C4 C6 C7 C8 2.9(3) . . . . ?
C4 C6 C7 C9 -170.88(16) . . . . ?
C6 C7 C8 C2 -0.6(3) . . . . ?
C9 C7 C8 C2 173.12(15) . . . . ?
C3 C2 C8 C7 -2.4(2) . . . . ?
C1 C2 C8 C7 178.86(15) . . . . ?
C10 N1 C9 C7 -2.8(2) . . . . ?
C14 N1 C9 C7 177.10(17) . . . . ?
C6 C7 C9 N1 -97.95(19) . . . . ?
C8 C7 C9 N1 88.4(2) . . . . ?
C14 N1 C10 C11 -1.1(3) . . . . ?
C9 N1 C10 C11 178.76(16) . . . . ?
N1 C10 C11 C12 0.3(3) . . . . ?
N1 C10 C11 C15 -178.93(16) . . . . ?
C10 C11 C12 C13 0.9(3) . . . . ?
C15 C11 C12 C13 -179.93(19) . . . . ?
C11 C12 C13 C14 -1.3(3) . . . . ?
C10 N1 C14 C13 0.7(3) . . . . ?
C9 N1 C14 C13 -179.16(19) . . . . ?
C12 C13 C14 N1 0.5(3) . . . . ?
Cd1 O5 C15 O6 12.5(3) . . . . ?
Cd1 O5 C15 C11 -169.16(12) . . . . ?
C10 C11 C15 O6 -22.8(3) . . . . ?
C12 C11 C15 O6 158.0(2) . . . . ?
C10 C11 C15 O5 158.69(17) . . . . ?
C12 C11 C15 O5 -20.5(3) . . . . ?

_refine_diff_density_max         1.077
_refine_diff_density_min         -1.014
_refine_diff_density_rms         0.095

_shelxl_version_number           2013-3

# start Validation Reply Form
_vrf_PLAT417_jp132               
;
PROBLEM: Short Inter D-H..H-D H3WB .. H3WB .. 1.05 Ang.
RESPONSE: These hydrogens were located in the electron density map; hence, 
these alerts do not stem from inconsistency of the crystal structure.
;
####################################################################### 
# 
# 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_jp134
_audit_block_doi                 10.5517/ccdc.csd.cc1jyzdv
_database_code_depnum_ccdc_archive 'CCDC 1428988'
_audit_update_record             
;
2017-02-24 deposited with the CCDC.
2017-03-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H13 Mn N O8, H2 O'
_chemical_formula_sum            'C15 H15 Mn N O9'
_chemical_formula_weight         408.22

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'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

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

_cell_length_a                   7.7335(3)
_cell_length_b                   10.1906(4)
_cell_length_c                   11.7904(4)
_cell_angle_alpha                66.3080(11)
_cell_angle_beta                 77.4597(11)
_cell_angle_gamma                71.6632(11)
_cell_volume                     803.26(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    23326
_cell_measurement_theta_min      1.897
_cell_measurement_theta_max      28.339

_exptl_crystal_description       plates
_exptl_crystal_colour            'clear white'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.688
_exptl_crystal_F_000             418
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    0.875
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.889
_exptl_absorpt_correction_T_max  0.926
_exptl_absorpt_process_details   'SADABS (Sheldrick 2014)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23326
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.897
_diffrn_reflns_theta_max         28.339
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4011
_reflns_number_gt                3684
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX2 (Bruker, 2013)'
_computing_cell_refinement       'APEX2 (Bruker, 2013)'
_computing_data_reduction        'APEX2 (Bruker, 2013)'
_computing_structure_solution    'SHELXT-2014/6 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    Diamond
_computing_publication_material  'SHELXT-2014/6 (Sheldrick, 2014)'


_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0306P)²+0.3642P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4011
_refine_ls_number_parameters     241
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0277
_refine_ls_R_factor_gt           0.0248
_refine_ls_wR_factor_ref         0.0652
_refine_ls_wR_factor_gt          0.0634
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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 0.85358(2) 0.90984(2) 0.93261(2) 0.01124(6) Uani 1 1 d . . . . .
O1 O 1.09213(14) 0.82096(11) 1.01958(11) 0.0261(2) Uani 1 1 d . . . . .
O2 O 1.26675(13) 0.86015(10) 1.12395(9) 0.01696(19) Uani 1 1 d . . . . .
O3 O 1.38396(13) 0.12462(10) 1.14826(9) 0.01751(19) Uani 1 1 d . . . . .
O4 O 1.16043(12) 0.30899(10) 1.05318(9) 0.01726(19) Uani 1 1 d . . . . .
O5 O 1.85245(16) 0.82345(12) 1.31480(9) 0.0266(2) Uani 1 1 d . . . . .
O6 O 1.83117(16) 0.75158(12) 1.52257(10) 0.0280(2) Uani 1 1 d . . . . .
N1 N 1.78278(14) 0.42312(11) 1.34810(10) 0.0131(2) Uani 1 1 d . . . . .
C1 C 1.21990(16) 0.77938(13) 1.08542(11) 0.0124(2) Uani 1 1 d . . . . .
C2 C 1.32776(16) 0.62001(13) 1.12115(11) 0.0105(2) Uani 1 1 d . . . . .
C3 C 1.26373(16) 0.51591(13) 1.10476(11) 0.0117(2) Uani 1 1 d . . . . .
H3A H 1.1500 0.5452 1.0719 0.014 Uiso 1 1 calc R U . . .
C4 C 1.36623(16) 0.36902(13) 1.13647(11) 0.0119(2) Uani 1 1 d . . . . .
C5 C 1.29974(17) 0.26057(14) 1.11114(11) 0.0129(2) Uani 1 1 d . . . . .
C6 C 1.53409(16) 0.32602(13) 1.18416(11) 0.0122(2) Uani 1 1 d . . . . .
H6A H 1.6023 0.2253 1.2082 0.015 Uiso 1 1 calc R U . . .
C7 C 1.60140(16) 0.43118(13) 1.19634(11) 0.0115(2) Uani 1 1 d . . . . .
C8 C 1.49756(16) 0.57786(13) 1.16513(11) 0.0110(2) Uani 1 1 d . . . . .
H8A H 1.5429 0.6494 1.1739 0.013 Uiso 1 1 calc R U . . .
C9 C 1.79102(17) 0.38899(14) 1.23504(12) 0.0145(2) Uani 1 1 d . . . . .
H9A H 1.8461 0.2818 1.2528 0.017 Uiso 1 1 calc R U . . .
H9B H 1.8695 0.4444 1.1661 0.017 Uiso 1 1 calc R U . . .
C10 C 1.81138(16) 0.55237(14) 1.33551(12) 0.0137(2) Uani 1 1 d . . . . .
H10A H 1.8446 0.6178 1.2552 0.016 Uiso 1 1 calc R U . . .
C11 C 1.79294(17) 0.59047(14) 1.43814(12) 0.0147(2) Uani 1 1 d . . . . .
C12 C 1.74671(18) 0.49190(15) 1.55504(12) 0.0182(3) Uani 1 1 d . . . . .
H12A H 1.7332 0.5160 1.6269 0.022 Uiso 1 1 calc R U . . .
C13 C 1.72029(19) 0.35832(15) 1.56665(13) 0.0209(3) Uani 1 1 d . . . . .
H13A H 1.6899 0.2900 1.6462 0.025 Uiso 1 1 calc R U . . .
C14 C 1.73877(18) 0.32624(14) 1.46091(13) 0.0182(3) Uani 1 1 d . . . . .
H14A H 1.7204 0.2354 1.4676 0.022 Uiso 1 1 calc R U . . .
C15 C 1.82672(18) 0.73569(15) 1.42460(12) 0.0173(2) Uani 1 1 d . . . . .
O1W O 0.68641(13) 0.88996(11) 1.11328(9) 0.0196(2) Uani 1 1 d . . . . .
H1O1 H 0.7388 0.8727 1.1750 0.037(5) Uiso 1 1 d R . . . .
H2O1 H 0.5936 0.9609 1.1115 0.044(6) Uiso 1 1 d R . . . .
O2W O 0.99921(13) 0.95116(10) 0.74295(9) 0.01885(19) Uani 1 1 d . . . . .
H1O2 H 1.0472 1.0223 0.7199 0.033(5) Uiso 1 1 d R . . . .
H2O2 H 0.9350 0.9730 0.6858 0.041(6) Uiso 1 1 d R . . . .
O3W O 1.74328(17) 0.99382(12) 1.59033(10) 0.0300(2) Uani 1 1 d . . . . .
H1O3 H 1.6719 0.9678 1.6552 0.050(7) Uiso 1 1 d R . . . .
H2O3 H 1.7719 0.9253 1.5621 0.045(6) Uiso 1 1 d R . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mn1 O1 2.0734(10) . ?
Mn1 O2 2.1085(9) 2_777 ?
Mn1 O4 2.2038(9) 2_767 ?
Mn1 O1W 2.2073(10) . ?
Mn1 O2W 2.2123(10) . ?
Mn1 O3 2.4172(9) 2_767 ?
Mn1 C5 2.6399(12) 2_767 ?
O1 C1 1.2505(16) . ?
O2 C1 1.2548(15) . ?
O2 Mn1 2.1085(9) 2_777 ?
O3 C5 1.2665(16) . ?
O3 Mn1 2.4172(9) 2_767 ?
O4 C5 1.2591(16) . ?
O4 Mn1 2.2038(9) 2_767 ?
O5 C15 1.2590(17) . ?
O6 C15 1.2380(16) . ?
N1 C10 1.3482(16) . ?
N1 C14 1.3488(17) . ?
N1 C9 1.4912(15) . ?
C1 C2 1.5038(16) . ?
C2 C8 1.3927(16) . ?
C2 C3 1.3944(16) . ?
C3 C4 1.3933(17) . ?
C4 C6 1.3980(17) . ?
C4 C5 1.5048(16) . ?
C5 Mn1 2.6398(12) 2_767 ?
C6 C7 1.3953(16) . ?
C7 C8 1.3948(16) . ?
C7 C9 1.5099(16) . ?
C10 C11 1.3795(17) . ?
C11 C12 1.3914(18) . ?
C11 C15 1.5228(17) . ?
C12 C13 1.3880(19) . ?
C13 C14 1.3793(19) . ?

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 O2 119.67(4) . 2_777 ?
O1 Mn1 O4 92.62(4) . 2_767 ?
O2 Mn1 O4 147.70(4) 2_777 2_767 ?
O1 Mn1 O1W 90.75(4) . . ?
O2 Mn1 O1W 87.15(4) 2_777 . ?
O4 Mn1 O1W 91.85(4) 2_767 . ?
O1 Mn1 O2W 94.14(4) . . ?
O2 Mn1 O2W 87.45(4) 2_777 . ?
O4 Mn1 O2W 91.35(4) 2_767 . ?
O1W Mn1 O2W 174.04(4) . . ?
O1 Mn1 O3 149.49(4) . 2_767 ?
O2 Mn1 O3 90.84(3) 2_777 2_767 ?
O4 Mn1 O3 56.89(3) 2_767 2_767 ?
O1W Mn1 O3 91.40(3) . 2_767 ?
O2W Mn1 O3 86.13(3) . 2_767 ?
O1 Mn1 C5 120.91(4) . 2_767 ?
O2 Mn1 C5 119.41(4) 2_777 2_767 ?
O4 Mn1 C5 28.35(4) 2_767 2_767 ?
O1W Mn1 C5 92.76(4) . 2_767 ?
O2W Mn1 C5 87.67(4) . 2_767 ?
O3 Mn1 C5 28.57(4) 2_767 2_767 ?
C1 O1 Mn1 169.46(10) . . ?
C1 O2 Mn1 121.40(8) . 2_777 ?
C5 O3 Mn1 85.52(7) . 2_767 ?
C5 O4 Mn1 95.45(7) . 2_767 ?
C10 N1 C14 121.32(11) . . ?
C10 N1 C9 119.66(10) . . ?
C14 N1 C9 118.96(11) . . ?
O1 C1 O2 125.33(11) . . ?
O1 C1 C2 117.76(11) . . ?
O2 C1 C2 116.91(10) . . ?
C8 C2 C3 119.78(11) . . ?
C8 C2 C1 119.48(10) . . ?
C3 C2 C1 120.66(10) . . ?
C4 C3 C2 120.13(11) . . ?
C3 C4 C6 119.96(11) . . ?
C3 C4 C5 119.18(11) . . ?
C6 C4 C5 120.75(11) . . ?
O4 C5 O3 122.02(11) . . ?
O4 C5 C4 118.29(11) . . ?
O3 C5 C4 119.69(11) . . ?
O4 C5 Mn1 56.21(6) . 2_767 ?
O3 C5 Mn1 65.90(6) . 2_767 ?
C4 C5 Mn1 173.64(9) . 2_767 ?
C7 C6 C4 119.94(11) . . ?
C8 C7 C6 119.77(11) . . ?
C8 C7 C9 119.87(10) . . ?
C6 C7 C9 120.24(11) . . ?
C2 C8 C7 120.35(11) . . ?
N1 C9 C7 110.43(10) . . ?
N1 C10 C11 120.65(11) . . ?
C10 C11 C12 118.65(12) . . ?
C10 C11 C15 120.87(11) . . ?
C12 C11 C15 120.47(11) . . ?
C13 C12 C11 120.01(12) . . ?
C14 C13 C12 119.01(12) . . ?
N1 C14 C13 120.35(12) . . ?
O6 C15 O5 127.68(13) . . ?
O6 C15 C11 116.27(12) . . ?
O5 C15 C11 116.01(11) . . ?

_refine_diff_density_max         0.432
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.057

_shelxl_version_number           2013-4

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

data_jv238_sq
_audit_block_doi                 10.5517/ccdc.csd.cc1jyzfw
_database_code_depnum_ccdc_archive 'CCDC 1428989'
_audit_update_record             
;
2017-02-24 deposited with the CCDC.
2017-03-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H33 Cu N2 O18.50'
_chemical_formula_weight         781.12

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

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

_cell_length_a                   11.7780(7)
_cell_length_b                   12.1842(8)
_cell_length_c                   13.5056(9)
_cell_angle_alpha                95.876(2)
_cell_angle_beta                 98.626(2)
_cell_angle_gamma                112.384(2)
_cell_volume                     1744.6(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    68563
_cell_measurement_theta_min      1.836
_cell_measurement_theta_max      28.380

_exptl_crystal_description       plates
_exptl_crystal_colour            blue
__exptl_crystal_density_meas     ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_F_000             808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_exptl_absorpt_coefficient_mu    0.709
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.907
_exptl_absorpt_correction_T_max  0.959
_exptl_absorpt_process_details   'SADABS (Sheldrick 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            68686
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_av_R_equivalents  0.0430
_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       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.549
_diffrn_reflns_theta_max         28.380
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8703
_reflns_number_gt                7543
_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       'APEX2 (Bruker, 2013)'
_computing_cell_refinement       'APEX2 (Bruker, 2013)'
_computing_data_reduction        'APEX2 (Bruker, 2013)'
_computing_structure_solution    'SHELXT-2014/6 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    Diamond
_computing_publication_material  'SHELXT-2014/6 (Sheldrick, 2014)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0633P)²+1.4675P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8703
_refine_ls_number_parameters     480
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_ref         0.1213
_refine_ls_wR_factor_gt          0.1167
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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 0.06708(2) 0.08269(2) 0.34113(2) 0.02505(8) Uani 1 1 d D . . . .
O1 O 0.16531(14) -0.01468(13) 0.33634(13) 0.0294(3) Uani 1 1 d . . . . .
O2 O 0.22832(15) 0.05608(16) 0.50312(14) 0.0414(4) Uani 1 1 d . . . . .
O3 O 0.47028(18) -0.09460(17) 0.71827(11) 0.0451(5) Uani 1 1 d . . . . .
H3 H 0.4941 -0.1110 0.7745 0.054 Uiso 1 1 d R U . . .
O4 O 0.54417(18) -0.22923(19) 0.66108(13) 0.0459(5) Uani 1 1 d . . . . .
O5 O 0.55834(18) -0.0949(2) -0.10220(12) 0.0547(6) Uani 1 1 d . . . . .
O6 O 0.36106(16) -0.19272(15) -0.08462(11) 0.0368(4) Uani 1 1 d . . . . .
N1 N 0.48754(16) -0.21329(15) 0.21103(12) 0.0224(3) Uani 1 1 d . . . . .
C1 C 0.22654(18) -0.00888(18) 0.42446(17) 0.0273(4) Uani 1 1 d . . . . .
C2 C 0.30145(17) -0.08414(17) 0.43304(15) 0.0210(4) Uani 1 1 d . . . . .
C3 C 0.35752(18) -0.08956(18) 0.52977(15) 0.0239(4) Uani 1 1 d . . . . .
H3A H 0.3477 -0.0457 0.5878 0.029 Uiso 1 1 calc R U . . .
C4 C 0.42732(18) -0.15806(18) 0.54222(14) 0.0226(4) Uani 1 1 d . . . . .
C5 C 0.4869(2) -0.1642(2) 0.64695(15) 0.0315(5) Uani 1 1 d . . . . .
C6 C 0.44129(17) -0.22257(17) 0.45690(14) 0.0209(4) Uani 1 1 d . . . . .
H6 H 0.4890 -0.2699 0.4650 0.025 Uiso 1 1 calc R U . . .
C7 C 0.38585(17) -0.21790(16) 0.36017(13) 0.0185(3) Uani 1 1 d . . . . .
C8 C 0.31493(17) -0.14923(17) 0.34791(14) 0.0193(3) Uani 1 1 d . . . . .
H8 H 0.2760 -0.1468 0.2817 0.023 Uiso 1 1 calc R U . . .
C9 C 0.39886(19) -0.29094(17) 0.26868(14) 0.0227(4) Uani 1 1 d . . . . .
H9A H 0.4295 -0.3513 0.2913 0.027 Uiso 1 1 calc R U . . .
H9B H 0.3155 -0.3349 0.2231 0.027 Uiso 1 1 calc R U . . .
C10 C 0.44454(19) -0.20707(18) 0.11462(14) 0.0230(4) Uani 1 1 d . . . . .
H10 H 0.3576 -0.2477 0.0853 0.028 Uiso 1 1 calc R U . . .
C11 C 0.5263(2) -0.1419(2) 0.05816(15) 0.0311(5) Uani 1 1 d . . . . .
C12 C 0.6521(2) -0.0815(3) 0.10322(18) 0.0521(8) Uani 1 1 d . . . . .
H12 H 0.7100 -0.0369 0.0653 0.062 Uiso 1 1 calc R U . . .
C13 C 0.6936(2) -0.0860(3) 0.2035(2) 0.0603(10) Uani 1 1 d . . . . .
H13 H 0.7793 -0.0424 0.2356 0.072 Uiso 1 1 calc R U . . .
C14 C 0.6094(2) -0.1543(3) 0.25591(17) 0.0396(6) Uani 1 1 d . . . . .
H14 H 0.6372 -0.1598 0.3242 0.047 Uiso 1 1 calc R U . . .
C15 C 0.4758(2) -0.1433(2) -0.05156(15) 0.0336(5) Uani 1 1 d . . . . .
O21 O -0.02815(14) 0.18144(13) 0.34905(11) 0.0262(3) Uani 1 1 d . . . . .
O22 O 0.02360(17) 0.21367(15) 0.51869(12) 0.0363(4) Uani 1 1 d . . . . .
O23 O -0.08684(14) 0.48649(14) 0.72480(10) 0.0287(3) Uani 1 1 d . . . . .
H23 H -0.0936 0.5171 0.7810 0.034 Uiso 1 1 d R U . . .
O24 O -0.23067(16) 0.55144(14) 0.66047(11) 0.0315(3) Uani 1 1 d . . . . .
O25 O -0.16947(16) 0.39704(14) -0.06817(11) 0.0344(4) Uani 1 1 d . . . . .
O26 O -0.08122(16) 0.58392(14) -0.09893(11) 0.0338(4) Uani 1 1 d . . . . .
N21 N -0.20733(15) 0.51793(14) 0.21391(11) 0.0195(3) Uani 1 1 d . . . . .
C21 C -0.02875(18) 0.22884(16) 0.43723(15) 0.0212(4) Uani 1 1 d . . . . .
C22 C -0.09641(16) 0.31111(15) 0.44234(13) 0.0168(3) Uani 1 1 d . . . . .
C23 C -0.09744(16) 0.36579(15) 0.53819(13) 0.0169(3) Uani 1 1 d . . . . .
H23A H -0.0560 0.3502 0.5976 0.020 Uiso 1 1 calc R U . . .
C24 C -0.15843(17) 0.44247(15) 0.54709(13) 0.0170(3) Uani 1 1 d . . . . .
C25 C -0.16119(18) 0.49944(16) 0.64984(14) 0.0202(4) Uani 1 1 d . . . . .
C26 C -0.21971(17) 0.46466(16) 0.45959(13) 0.0179(3) Uani 1 1 d . . . . .
H26 H -0.2621 0.5168 0.4655 0.021 Uiso 1 1 calc R U . . .
C27 C -0.21914(17) 0.41097(16) 0.36388(13) 0.0172(3) Uani 1 1 d . . . . .
C28 C -0.15765(17) 0.33350(16) 0.35547(13) 0.0178(3) Uani 1 1 d . . . . .
H28 H -0.1577 0.2960 0.2902 0.021 Uiso 1 1 calc R U . . .
C29 C -0.29089(18) 0.43136(18) 0.27006(14) 0.0215(4) Uani 1 1 d . . . . .
H29A H -0.3391 0.3532 0.2238 0.026 Uiso 1 1 calc R U . . .
H29B H -0.3516 0.4629 0.2903 0.026 Uiso 1 1 calc R U . . .
C30 C -0.19780(17) 0.47827(17) 0.12008(13) 0.0197(3) Uani 1 1 d . . . . .
H30 H -0.2400 0.3950 0.0918 0.024 Uiso 1 1 calc R U . . .
C31 C -0.12722(19) 0.55735(18) 0.06431(14) 0.0234(4) Uani 1 1 d . . . . .
C32 C -0.0634(2) 0.6778(2) 0.10823(16) 0.0353(5) Uani 1 1 d . . . . .
H32 H -0.0145 0.7339 0.0713 0.042 Uiso 1 1 calc R U . . .
C33 C -0.0713(3) 0.7164(2) 0.20640(17) 0.0392(6) Uani 1 1 d . . . . .
H33 H -0.0256 0.7983 0.2379 0.047 Uiso 1 1 calc R U . . .
C34 C -0.1457(2) 0.63510(19) 0.25757(15) 0.0287(4) Uani 1 1 d . . . . .
H34 H -0.1539 0.6614 0.3238 0.034 Uiso 1 1 calc R U . . .
C35 C -0.12643(18) 0.50695(19) -0.04291(14) 0.0242(4) Uani 1 1 d . . . . .
O1W O -0.06687(13) -0.05426(13) 0.37918(11) 0.0239(3) Uani 1 1 d . . . . .
H1WA H -0.0431 -0.0986 0.4130 0.029 Uiso 1 1 d R U . . .
H1WB H -0.1162 -0.0405 0.4126 0.029 Uiso 1 1 d R U . . .
O2W O -0.0119(2) 0.0323(2) 0.17431(16) 0.0594(6) Uani 1 1 d D . . . .
H2WA H -0.0358 0.0798 0.1453 0.089 Uiso 1 1 d DR U . . .
H2WB H 0.0343 0.0198 0.1368 0.089 Uiso 1 1 d DR U . . .
O3W O 0.2296(3) 0.2326(3) 0.3702(4) 0.0401(8) Uani 0.5 1 d . . P A 1
H3WA H 0.2275 0.2794 0.3291 0.060 Uiso 0.5 1 d R U P A 1
H3WB H 0.2916 0.2155 0.3655 0.060 Uiso 0.5 1 d R U P A 1
O3W' O 0.2037(3) 0.2162(3) 0.2989(4) 0.0379(8) Uani 0.5 1 d . . P A 2
H3WC H 0.2713 0.2070 0.3109 0.057 Uiso 0.5 1 d R U P A 2
H3WD H 0.2137 0.2827 0.3317 0.057 Uiso 0.5 1 d R U P A 2
O4W O 0.1167(2) -0.18949(17) -0.08007(15) 0.0484(5) Uani 1 1 d D . . . .
H4WA H 0.1887 -0.1887 -0.0781 0.100(17) Uiso 1 1 d DR . . . .
H4WB H 0.0605 -0.2556 -0.0758 0.103(16) Uiso 1 1 d DR . . . .
O7W O 0.3390(2) 0.3293(2) 0.5943(2) 0.0682(6) Uani 1 1 d . . . . .
H7WA H 0.2934 0.2825 0.5405 0.102 Uiso 1 1 d R U . . .
H7WB H 0.3221 0.2952 0.6444 0.102 Uiso 1 1 d R U . . .
O5W O 0.1630(3) -0.0214(3) 0.0930(2) 0.0921(10) Uani 1 1 d . . . . .
H5WA H 0.2285 0.0413 0.0989 0.138 Uiso 1 1 d R U . . .
H5WB H 0.1573 -0.0715 0.0428 0.138 Uiso 1 1 d R U . . .
O6W O 0.4747(4) 0.4635(4) 0.4374(4) 0.0571(11) Uani 0.5 1 d . . P B -1
H6WA H 0.3960 0.4349 0.4247 0.086 Uiso 0.5 1 d R U P B -1
H6WB H 0.5017 0.4996 0.3905 0.086 Uiso 0.5 1 d R U P B -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
Cu1 O21 1.9378(14) . ?
Cu1 O1 1.9499(14) . ?
Cu1 O1W 1.9878(14) . ?
Cu1 O3W' 2.008(4) . ?
Cu1 O3W 2.030(4) . ?
Cu1 O2W 2.230(2) . ?
O1 C1 1.276(3) . ?
O2 C1 1.251(3) . ?
O3 C5 1.305(3) . ?
O4 C5 1.232(3) . ?
O5 C15 1.267(3) . ?
O6 C15 1.238(3) . ?
N1 C14 1.344(3) . ?
N1 C10 1.345(2) . ?
N1 C9 1.495(2) . ?
C1 C2 1.497(3) . ?
C2 C3 1.393(3) . ?
C2 C8 1.393(3) . ?
C3 C4 1.382(3) . ?
C4 C6 1.394(3) . ?
C4 C5 1.504(3) . ?
C6 C7 1.387(2) . ?
C7 C8 1.394(3) . ?
C7 C9 1.509(2) . ?
C10 C11 1.379(3) . ?
C11 C12 1.384(3) . ?
C11 C15 1.507(3) . ?
C12 C13 1.383(3) . ?
C13 C14 1.371(3) . ?
O21 C21 1.271(2) . ?
O22 C21 1.245(2) . ?
O23 C25 1.299(2) . ?
O24 C25 1.226(2) . ?
O25 C35 1.226(3) . ?
O26 C35 1.273(2) . ?
N21 C30 1.346(2) . ?
N21 C34 1.350(3) . ?
N21 C29 1.501(2) . ?
C21 C22 1.502(2) . ?
C22 C28 1.390(2) . ?
C22 C23 1.398(2) . ?
C23 C24 1.385(3) . ?
C24 C26 1.396(2) . ?
C24 C25 1.497(2) . ?
C26 C27 1.390(2) . ?
C27 C28 1.397(2) . ?
C27 C29 1.511(2) . ?
C30 C31 1.383(3) . ?
C31 C32 1.385(3) . ?
C31 C35 1.517(2) . ?
C32 C33 1.389(3) . ?
C33 C34 1.374(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O21 Cu1 O1 178.64(7) . . ?
O21 Cu1 O1W 91.58(6) . . ?
O1 Cu1 O1W 88.67(6) . . ?
O21 Cu1 O3W' 90.29(11) . . ?
O1 Cu1 O3W' 89.49(11) . . ?
O1W Cu1 O3W' 177.68(12) . . ?
O21 Cu1 O3W 90.56(10) . . ?
O1 Cu1 O3W 88.63(10) . . ?
O1W Cu1 O3W 154.33(14) . . ?
O21 Cu1 O2W 88.05(7) . . ?
O1 Cu1 O2W 93.26(7) . . ?
O1W Cu1 O2W 95.70(7) . . ?
O3W' Cu1 O2W 82.99(14) . . ?
O3W Cu1 O2W 109.94(15) . . ?
C1 O1 Cu1 111.55(13) . . ?
C14 N1 C10 121.57(18) . . ?
C14 N1 C9 119.03(17) . . ?
C10 N1 C9 119.36(16) . . ?
O2 C1 O1 124.1(2) . . ?
O2 C1 C2 118.5(2) . . ?
O1 C1 C2 117.39(18) . . ?
C3 C2 C8 119.68(18) . . ?
C3 C2 C1 118.25(18) . . ?
C8 C2 C1 122.07(18) . . ?
C4 C3 C2 120.72(17) . . ?
C3 C4 C6 119.50(17) . . ?
C3 C4 C5 120.47(19) . . ?
C6 C4 C5 120.02(19) . . ?
O4 C5 O3 125.3(2) . . ?
O4 C5 C4 122.2(2) . . ?
O3 C5 C4 112.6(2) . . ?
C7 C6 C4 120.29(18) . . ?
C6 C7 C8 120.05(17) . . ?
C6 C7 C9 119.67(17) . . ?
C8 C7 C9 120.25(16) . . ?
C2 C8 C7 119.74(17) . . ?
N1 C9 C7 111.84(15) . . ?
N1 C10 C11 120.17(18) . . ?
C10 C11 C12 118.80(19) . . ?
C10 C11 C15 118.57(19) . . ?
C12 C11 C15 122.59(19) . . ?
C13 C12 C11 120.0(2) . . ?
C14 C13 C12 119.1(2) . . ?
N1 C14 C13 120.3(2) . . ?
O6 C15 O5 126.2(2) . . ?
O6 C15 C11 118.79(19) . . ?
O5 C15 C11 115.0(2) . . ?
C21 O21 Cu1 117.24(12) . . ?
C30 N21 C34 121.19(17) . . ?
C30 N21 C29 119.57(16) . . ?
C34 N21 C29 119.21(16) . . ?
O22 C21 O21 125.16(18) . . ?
O22 C21 C22 118.03(17) . . ?
O21 C21 C22 116.79(16) . . ?
C28 C22 C23 119.68(16) . . ?
C28 C22 C21 122.15(16) . . ?
C23 C22 C21 118.16(16) . . ?
C24 C23 C22 120.45(16) . . ?
C23 C24 C26 119.61(16) . . ?
C23 C24 C25 120.40(16) . . ?
C26 C24 C25 119.98(16) . . ?
O24 C25 O23 123.95(17) . . ?
O24 C25 C24 121.55(17) . . ?
O23 C25 C24 114.48(16) . . ?
C27 C26 C24 120.44(16) . . ?
C26 C27 C28 119.64(16) . . ?
C26 C27 C29 119.80(16) . . ?
C28 C27 C29 120.48(16) . . ?
C22 C28 C27 120.17(16) . . ?
N21 C29 C27 112.95(15) . . ?
N21 C30 C31 120.77(17) . . ?
C30 C31 C32 118.61(17) . . ?
C30 C31 C35 117.68(17) . . ?
C32 C31 C35 123.70(18) . . ?
C31 C32 C33 119.75(19) . . ?
C34 C33 C32 119.5(2) . . ?
N21 C34 C33 120.14(18) . . ?
O25 C35 O26 125.93(18) . . ?
O25 C35 C31 117.83(18) . . ?
O26 C35 C31 116.24(17) . . ?

_refine_diff_density_max         0.998
_refine_diff_density_min         -0.772
_refine_diff_density_rms         0.071

_shelxl_version_number           2013-3


# start Validation Reply Form
_vrf_PLAT415_jv238_sq            
;
PROBLEM: Short Inter D-H..H-X  H7WB..H14 1.94 Ang.
RESPONSE: These hydrogens were located in the electron density map; hence, these 
alerts do not stem from the inconsistency of the crystal structure.
;
_vrf_PLAT420_jv238_sq            
;
PROBLEM:  D-H Without Acceptor O7W -- H7WB ... Please Check 
RESPONSE: All significant residual electron densities could be assigned to water 
molecules, and thus, no missing acceptor atoms can be found; 
hence, this alert does not stem from inconsistency of the crystal structure.
;
# end Validation Reply Form

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

data_an152
_audit_block_doi                 10.5517/ccdc.csd.cc1jyzgx
_database_code_depnum_ccdc_archive 'CCDC 1428990'
_audit_update_record             
;
2017-02-24 deposited with the CCDC.
2017-03-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H16 Mn N O9.50'
_chemical_formula_weight         417.23

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

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

_cell_length_a                   8.6474(4)
_cell_length_b                   10.0521(5)
_cell_length_c                   10.3075(5)
_cell_angle_alpha                75.8767(14)
_cell_angle_beta                 66.3576(13)
_cell_angle_gamma                83.4926(15)
_cell_volume                     795.84(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    24487
_cell_measurement_theta_min      2.089
_cell_measurement_theta_max      28.354

_exptl_crystal_description       plates
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.741
_exptl_crystal_F_000             428
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_exptl_absorpt_coefficient_mu    0.887
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.850
_exptl_absorpt_correction_T_max  0.901
_exptl_absorpt_process_details   'SADABS (Sheldrick 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24545
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.089
_diffrn_reflns_theta_max         28.354
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3977
_reflns_number_gt                3626
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX2 (Bruker, 2013)'
_computing_cell_refinement       'APEX2 (Bruker, 2013)'
_computing_data_reduction        'APEX2 (Bruker, 2013)'
_computing_structure_solution    'SHELXT-2014/6 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    Diamond
_computing_publication_material  'SHELXT-2014/6 (Sheldrick, 2014)'
_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0355P)²+0.5529P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3977
_refine_ls_number_parameters     247
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0318
_refine_ls_R_factor_gt           0.0279
_refine_ls_wR_factor_ref         0.0734
_refine_ls_wR_factor_gt          0.0709
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.076
_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 0.15371(3) 0.07151(2) 0.07755(2) 0.01157(7) Uani 1 1 d D . . . .
O1 O -0.08881(14) -0.01659(13) 0.18965(12) 0.0249(3) Uani 1 1 d . . . . .
O2 O -0.26981(15) -0.12849(11) 0.15314(11) 0.0204(2) Uani 1 1 d . . . . .
O3 O -0.14004(13) -0.06495(11) 0.69821(11) 0.0173(2) Uani 1 1 d . . . . .
O4 O -0.37332(13) -0.14360(11) 0.88186(11) 0.0181(2) Uani 1 1 d . . . . .
O5 O -0.8793(2) -0.35852(13) 0.11320(16) 0.0388(4) Uani 1 1 d D . . . .
O6 O -0.88211(17) -0.57892(12) 0.22449(13) 0.0289(3) Uani 1 1 d . . . . .
N1 N -0.77943(15) -0.33735(13) 0.54736(13) 0.0141(2) Uani 1 1 d . . . . .
C1 C -0.21715(17) -0.08714(14) 0.23318(14) 0.0127(3) Uani 1 1 d . . . . .
C2 C -0.31828(17) -0.12676(13) 0.39461(14) 0.0113(2) Uani 1 1 d . . . . .
C3 C -0.25840(17) -0.10057(14) 0.49277(15) 0.0120(2) Uani 1 1 d . . . . .
H3 H -0.1536 -0.0561 0.4582 0.014 Uiso 1 1 calc R U . . .
C4 C -0.35226(17) -0.13963(14) 0.64197(14) 0.0117(2) Uani 1 1 d . . . . .
C5 C -0.28491(18) -0.11439(14) 0.74729(15) 0.0129(3) Uani 1 1 d . . . . .
C6 C -0.50658(17) -0.20323(14) 0.69178(15) 0.0130(3) Uani 1 1 d . . . . .
H6 H -0.5707 -0.2296 0.7931 0.016 Uiso 1 1 calc R U . . .
C7 C -0.56793(17) -0.22864(14) 0.59409(15) 0.0126(3) Uani 1 1 d . . . . .
C8 C -0.47326(17) -0.19125(14) 0.44607(14) 0.0127(3) Uani 1 1 d . . . . .
H8 H -0.5140 -0.2096 0.3793 0.015 Uiso 1 1 calc R U . . .
C9 C -0.74010(18) -0.29283(16) 0.65704(15) 0.0169(3) Uani 1 1 d . . . . .
H9A H -0.7444 -0.3730 0.7363 0.020 Uiso 1 1 calc R U . . .
H9B H -0.8272 -0.2255 0.6993 0.020 Uiso 1 1 calc R U . . .
C10 C -0.73035(18) -0.46358(15) 0.52076(17) 0.0175(3) Uani 1 1 d . . . . .
H10 H -0.6744 -0.5244 0.5749 0.021 Uiso 1 1 calc R U . . .
C11 C -0.76114(19) -0.50453(15) 0.41538(17) 0.0183(3) Uani 1 1 d . . . . .
H11 H -0.7293 -0.5943 0.3986 0.022 Uiso 1 1 calc R U . . .
C12 C -0.83887(17) -0.41407(14) 0.33370(16) 0.0145(3) Uani 1 1 d . . . . .
C13 C -0.89012(18) -0.28542(15) 0.36518(16) 0.0155(3) Uani 1 1 d . . . . .
H13 H -0.9454 -0.2225 0.3119 0.019 Uiso 1 1 calc R U . . .
C14 C -0.86050(18) -0.24955(15) 0.47367(16) 0.0160(3) Uani 1 1 d . . . . .
H14 H -0.8975 -0.1624 0.4966 0.019 Uiso 1 1 calc R U . . .
C15 C -0.86994(19) -0.45457(16) 0.21287(17) 0.0176(3) Uani 1 1 d . . . . .
O1W O 0.28647(14) -0.12259(11) 0.05573(13) 0.0235(2) Uani 1 1 d D . . . .
H1WA H 0.2361 -0.1944 0.0686 0.035 Uiso 1 1 d DR U . . .
H1WB H 0.3888 -0.1273 0.0012 0.035 Uiso 1 1 d DR U . . .
O2W O 0.06355(15) 0.28297(11) 0.05546(12) 0.0230(2) Uani 1 1 d D . . . .
H2WA H 0.0794 0.3381 0.0983 0.035 Uiso 1 1 d DR U . . .
H2WB H 0.0104 0.3221 0.0036 0.035 Uiso 1 1 d DR U . . .
O4W O -0.4900(6) -0.4526(4) -0.0042(6) 0.0757(14) Uani 0.5 1 d . . P A -1
H4WA H -0.4034 -0.4110 -0.0670 0.113 Uiso 0.5 1 d DR U P A -1
H4WB H -0.5746 -0.3998 0.0060 0.113 Uiso 0.5 1 d DR U P A -1
O3W O -0.3950(2) -0.40644(18) 0.2055(2) 0.0649(5) Uani 1 1 d G . . . .
H3WA H -0.4206 -0.4195 0.1391 0.097 Uiso 1 1 d R U . . .
H3WB H -0.3386 -0.3346 0.1757 0.097 Uiso 1 1 d R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mn1 O1 2.1203(11) . ?
Mn1 O2 2.1309(10) 2 ?
O1 C1 1.2489(17) . ?
O2 C1 1.2539(17) . ?
O2 Mn1 2.1310(10) 2 ?
O3 C5 1.2579(17) . ?
O4 C5 1.2634(17) . ?
O5 C15 1.249(2) . ?
O6 C15 1.2387(19) . ?
N1 C14 1.3443(19) . ?
N1 C10 1.3490(19) . ?
N1 C9 1.4777(18) . ?
C1 C2 1.5102(18) . ?
C2 C3 1.3937(18) . ?
C2 C8 1.3988(18) . ?
C3 C4 1.3980(19) . ?
C4 C6 1.3917(19) . ?
C4 C5 1.5024(18) . ?
C6 C7 1.3947(19) . ?
C7 C8 1.3883(19) . ?
C7 C9 1.5142(19) . ?
C10 C11 1.377(2) . ?
C11 C12 1.389(2) . ?
C12 C13 1.391(2) . ?
C12 C15 1.5264(19) . ?
C13 C14 1.376(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 O2 122.94(4) . 2 ?
C1 O1 Mn1 165.65(11) . . ?
C1 O2 Mn1 122.04(9) . 2 ?
C14 N1 C10 121.29(12) . . ?
C14 N1 C9 119.05(12) . . ?
C10 N1 C9 119.64(12) . . ?
O1 C1 O2 125.14(13) . . ?
O1 C1 C2 118.17(12) . . ?
O2 C1 C2 116.69(12) . . ?
C3 C2 C8 119.69(12) . . ?
C3 C2 C1 120.74(12) . . ?
C8 C2 C1 119.57(12) . . ?
C2 C3 C4 120.09(12) . . ?
C6 C4 C3 119.66(12) . . ?
C6 C4 C5 120.50(12) . . ?
C3 C4 C5 119.83(12) . . ?
O3 C5 O4 121.64(12) . . ?
O3 C5 C4 118.54(12) . . ?
O4 C5 C4 119.82(12) . . ?
C4 C6 C7 120.53(13) . . ?
C8 C7 C6 119.60(12) . . ?
C8 C7 C9 123.20(12) . . ?
C6 C7 C9 117.17(12) . . ?
C7 C8 C2 120.42(12) . . ?
N1 C9 C7 112.48(11) . . ?
N1 C10 C11 120.19(14) . . ?
C10 C11 C12 119.77(14) . . ?
C11 C12 C13 118.61(13) . . ?
C11 C12 C15 121.13(13) . . ?
C13 C12 C15 120.25(13) . . ?
C14 C13 C12 119.81(13) . . ?
N1 C14 C13 120.26(13) . . ?
O6 C15 O5 127.45(15) . . ?
O6 C15 C12 116.32(13) . . ?
O5 C15 C12 116.22(13) . . ?

_refine_diff_density_max         0.658
_refine_diff_density_min         -0.603
_refine_diff_density_rms         0.059

_shelxl_version_number           2013-3

# start Validation Reply Form
_vrf_PLAT417_an152               
;
PROBLEM: Short Inter D-H..H-D H4WA .. H3WA .. 2.03 Ang.
RESPONSE: These hydrogens were located in the electron density map; hence, 
these alerts do not stem from inconsistency of the crystal structure.
;
####################################################################### 
# 
# 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_an149
_audit_block_doi                 10.5517/ccdc.csd.cc1jyzhy
_database_code_depnum_ccdc_archive 'CCDC 1428991'
_audit_update_record             
;
2017-02-24 deposited with the CCDC.
2017-03-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H19 Co N O11'
_chemical_formula_weight         448.24

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   11.2047(8)
_cell_length_b                   14.5919(9)
_cell_length_c                   11.9668(7)
_cell_angle_alpha                90
_cell_angle_beta                 116.9244(18)
_cell_angle_gamma                90
_cell_volume                     1744.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    22831
_cell_measurement_theta_min      2.039
_cell_measurement_theta_max      28.288

_exptl_crystal_description       plates
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.707
_exptl_crystal_F_000             924
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_exptl_absorpt_coefficient_mu    1.048
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.863
_exptl_absorpt_correction_T_max  0.926
_exptl_absorpt_process_details   'SADABS (Sheldrick 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22831
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_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         2.039
_diffrn_reflns_theta_max         28.288
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4328
_reflns_number_gt                3857
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX2 (Bruker, 2013)'
_computing_cell_refinement       'APEX2 (Bruker, 2013)'
_computing_data_reduction        'APEX2 (Bruker, 2013)'
_computing_structure_solution    'SHELXT-2014/6 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    Diamond
_computing_publication_material  'SHELXT-2014/6 (Sheldrick, 2014)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0340P)²+0.9903P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4328
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0267
_refine_ls_wR_factor_ref         0.0707
_refine_ls_wR_factor_gt          0.0680
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.99900(2) 0.86324(2) 0.71639(2) 0.01373(6) Uani 1 1 d . . . . .
O1 O 0.79021(10) 0.86702(7) 0.61220(10) 0.0189(2) Uani 1 1 d . . . . .
O2 O 0.87894(10) 0.94826(7) 0.78563(10) 0.0185(2) Uani 1 1 d . . . . .
O3 O 0.31804(12) 0.77578(8) 0.46444(14) 0.0365(3) Uani 1 1 d . . . . .
O4 O 0.16845(10) 0.87729(7) 0.46245(10) 0.0184(2) Uani 1 1 d . . . . .
O5 O 0.18826(13) 1.40605(8) 0.34766(11) 0.0326(3) Uani 1 1 d . . . . .
O6 O 0.34470(11) 1.50046(7) 0.47923(10) 0.0239(2) Uani 1 1 d . . . . .
N1 N 0.42615(12) 1.20404(8) 0.70763(10) 0.0142(2) Uani 1 1 d . . . . .
C1 C 0.77722(14) 0.91948(9) 0.69031(13) 0.0149(3) Uani 1 1 d . . . . .
C2 C 0.63929(13) 0.94522(9) 0.66959(12) 0.0135(2) Uani 1 1 d . . . . .
C3 C 0.53032(14) 0.89264(9) 0.59030(12) 0.0137(2) Uani 1 1 d . . . . .
H3 H 0.5434 0.8421 0.5471 0.016 Uiso 1 1 calc R U . . .
C5 C 0.28686(14) 0.85137(9) 0.49314(14) 0.0162(3) Uani 1 1 d . . . . .
C6 C 0.38231(14) 0.98847(9) 0.63610(13) 0.0144(3) Uani 1 1 d . . . . .
H6 H 0.2948 1.0037 0.6241 0.017 Uiso 1 1 calc R U . . .
C7 C 0.49206(14) 1.04110(9) 0.71643(12) 0.0137(3) Uani 1 1 d . . . . .
C8 C 0.61950(14) 1.01919(9) 0.73316(13) 0.0148(3) Uani 1 1 d . . . . .
H8 H 0.6939 1.0548 0.7883 0.018 Uiso 1 1 calc R U . . .
C9 C 0.47400(15) 1.12068(9) 0.78814(13) 0.0167(3) Uani 1 1 d . . . . .
H9A H 0.4084 1.1038 0.8188 0.020 Uiso 1 1 calc R U . . .
H9B H 0.5603 1.1343 0.8619 0.020 Uiso 1 1 calc R U . . .
C14 C 0.51485(14) 1.25566(10) 0.68812(13) 0.0172(3) Uani 1 1 d . . . . .
H14 H 0.6073 1.2405 0.7293 0.021 Uiso 1 1 calc R U . . .
C10 C 0.29480(14) 1.22427(9) 0.65190(13) 0.0174(3) Uani 1 1 d . . . . .
H10 H 0.2345 1.1883 0.6693 0.021 Uiso 1 1 calc R U . . .
C11 C 0.24727(14) 1.29670(10) 0.56983(14) 0.0182(3) Uani 1 1 d . . . . .
H11 H 0.1543 1.3104 0.5297 0.022 Uiso 1 1 calc R U . . .
C12 C 0.33625(14) 1.34956(9) 0.54624(13) 0.0156(3) Uani 1 1 d . . . . .
C13 C 0.47239(14) 1.33023(10) 0.60893(13) 0.0169(3) Uani 1 1 d . . . . .
H13 H 0.5352 1.3678 0.5974 0.020 Uiso 1 1 calc R U . . .
C4 C 0.40175(13) 0.91349(9) 0.57364(12) 0.0135(2) Uani 1 1 d . . . . .
C15 C 0.28512(15) 1.42621(9) 0.45089(13) 0.0174(3) Uani 1 1 d . . . . .
O1W O 1.07023(15) 0.79654(8) 0.61111(13) 0.0359(3) Uani 1 1 d . . . . .
H1WA H 1.0691 0.7398 0.5991 0.043 Uiso 1 1 d R U . . .
H1WB H 1.0941 0.8245 0.5632 0.043 Uiso 1 1 d R U . . .
O2W O 1.16721(11) 0.86840(7) 0.88159(11) 0.0254(3) Uani 1 1 d . . . . .
H2WA H 1.2193 0.9092 0.8801 0.038 Uiso 1 1 d R U . . .
H2WB H 1.2077 0.8180 0.8964 0.038 Uiso 1 1 d R U . . .
O3W O 0.97079(10) 0.73411(7) 0.78392(10) 0.0197(2) Uani 1 1 d . . . . .
H3WA H 0.9195 0.6950 0.7335 0.024 Uiso 1 1 d R U . . .
H3WB H 1.0357 0.7046 0.8379 0.024 Uiso 1 1 d R U . . .
O4W O 1.03789(11) 0.98740(7) 0.64794(9) 0.0185(2) Uani 1 1 d . . . . .
H4WA H 0.9697 1.0174 0.6004 0.022 Uiso 1 1 d R U . . .
H4WB H 1.0809 1.0224 0.7087 0.022 Uiso 1 1 d R U . . .
O5W O 1.06965(13) 0.61508(8) 0.57360(11) 0.0304(3) Uani 1 1 d . . . . .
H5WA H 1.0807 0.5671 0.6159 0.037 Uiso 1 1 d R U . . .
H5WB H 1.0856 0.6007 0.5137 0.037 Uiso 1 1 d R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 O1W 2.0205(12) . ?
Co1 O2W 2.0228(11) . ?
Co1 O1 2.0950(11) . ?
Co1 O4W 2.1133(10) . ?
Co1 O3W 2.1296(10) . ?
Co1 O2 2.2460(10) . ?
Co1 C1 2.4988(14) . ?
O1 C1 1.2665(17) . ?
O2 C1 1.2646(17) . ?
O3 C5 1.2511(18) . ?
O4 C5 1.2637(18) . ?
O5 C15 1.2554(18) . ?
O6 C15 1.2367(18) . ?
N1 C10 1.3450(18) . ?
N1 C14 1.3490(19) . ?
N1 C9 1.4926(17) . ?
C1 C2 1.4980(19) . ?
C2 C3 1.3895(19) . ?
C2 C8 1.3948(19) . ?
C3 C4 1.3955(19) . ?
C5 C4 1.5112(19) . ?
C6 C4 1.3967(19) . ?
C6 C7 1.3984(19) . ?
C7 C8 1.3865(19) . ?
C7 C9 1.5109(18) . ?
C14 C13 1.378(2) . ?
C10 C11 1.375(2) . ?
C11 C12 1.387(2) . ?
C12 C13 1.390(2) . ?
C12 C15 1.5131(19) . ?

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
O1W Co1 O2W 99.85(6) . . ?
O1W Co1 O1 106.95(5) . . ?
O2W Co1 O1 151.15(5) . . ?
O1W Co1 O4W 87.84(4) . . ?
O2W Co1 O4W 94.73(4) . . ?
O1 Co1 O4W 96.74(4) . . ?
O1W Co1 O3W 88.78(4) . . ?
O2W Co1 O3W 83.96(4) . . ?
O1 Co1 O3W 86.07(4) . . ?
O4W Co1 O3W 176.12(4) . . ?
O1W Co1 O2 165.42(5) . . ?
O2W Co1 O2 93.87(4) . . ?
O1 Co1 O2 60.73(4) . . ?
O4W Co1 O2 86.13(4) . . ?
O3W Co1 O2 97.59(4) . . ?
O1W Co1 C1 137.02(5) . . ?
O2W Co1 C1 122.93(5) . . ?
O1 Co1 C1 30.42(4) . . ?
O4W Co1 C1 92.18(4) . . ?
O3W Co1 C1 91.60(4) . . ?
O2 Co1 C1 30.32(4) . . ?
C1 O1 Co1 92.71(8) . . ?
C1 O2 Co1 85.96(8) . . ?
C10 N1 C14 121.21(12) . . ?
C10 N1 C9 119.43(12) . . ?
C14 N1 C9 119.30(12) . . ?
O2 C1 O1 120.57(13) . . ?
O2 C1 C2 120.46(12) . . ?
O1 C1 C2 118.96(12) . . ?
O2 C1 Co1 63.72(7) . . ?
O1 C1 Co1 56.87(7) . . ?
C2 C1 Co1 174.97(10) . . ?
C3 C2 C8 119.48(13) . . ?
C3 C2 C1 119.75(12) . . ?
C8 C2 C1 120.71(12) . . ?
C2 C3 C4 120.55(12) . . ?
O3 C5 O4 124.82(13) . . ?
O3 C5 C4 116.14(13) . . ?
O4 C5 C4 119.01(12) . . ?
C4 C6 C7 119.76(13) . . ?
C8 C7 C6 120.01(12) . . ?
C8 C7 C9 119.29(12) . . ?
C6 C7 C9 120.68(13) . . ?
C7 C8 C2 120.49(13) . . ?
N1 C9 C7 111.17(11) . . ?
N1 C14 C13 120.51(13) . . ?
N1 C10 C11 120.37(13) . . ?
C10 C11 C12 119.42(13) . . ?
C11 C12 C13 119.44(13) . . ?
C11 C12 C15 120.20(13) . . ?
C13 C12 C15 120.34(13) . . ?
C14 C13 C12 118.94(13) . . ?
C3 C4 C6 119.69(12) . . ?
C3 C4 C5 119.12(12) . . ?
C6 C4 C5 121.11(13) . . ?
O6 C15 O5 126.43(14) . . ?
O6 C15 C12 117.89(13) . . ?
O5 C15 C12 115.61(13) . . ?

_refine_diff_density_max         0.571
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.058

_shelxl_version_number           2013-3

####################################################################### 
# 
# 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_an153
_audit_block_doi                 10.5517/ccdc.csd.cc1jyzjz
_database_code_depnum_ccdc_archive 'CCDC 1428992'
_audit_update_record             
;
2017-02-24 deposited with the CCDC.
2017-03-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H15 N Ni O9'
_chemical_formula_weight         411.99

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'
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'
Ni Ni 0.3393 1.1124 '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                   7.4619(8)
_cell_length_b                   22.051(2)
_cell_length_c                   10.1124(12)
_cell_angle_alpha                90
_cell_angle_beta                 102.376(4)
_cell_angle_gamma                90
_cell_volume                     1625.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    20684
_cell_measurement_theta_min      1.847
_cell_measurement_theta_max      28.357

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.684
_exptl_crystal_F_000             848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    1.246
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.767
_exptl_absorpt_correction_T_max  0.869
_exptl_absorpt_process_details   'SADABS (Sheldrick 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20684
_diffrn_reflns_av_unetI/netI     0.0508
_diffrn_reflns_av_R_equivalents  0.0646
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.847
_diffrn_reflns_theta_max         28.357
_diffrn_reflns_theta_full        25.242
_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 0.999
_reflns_number_total             4044
_reflns_number_gt                3281
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX2 (Bruker, 2013)'
_computing_cell_refinement       'APEX2 (Bruker, 2013)'
_computing_data_reduction        'APEX2 (Bruker, 2013)'
_computing_structure_solution    'SHELXT-2014/6 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    Diamond
_computing_publication_material  'SHELXT-2014/6 (Sheldrick, 2014)'
_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0260P)²+1.7410P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4044
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0532
_refine_ls_R_factor_gt           0.0393
_refine_ls_wR_factor_ref         0.0896
_refine_ls_wR_factor_gt          0.0840
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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 0.26294(4) 0.92069(2) 1.01529(3) 0.01288(9) Uani 1 1 d . . . . .
O1 O 0.2507(2) 0.96535(7) 0.83819(16) 0.0157(3) Uani 1 1 d . . . . .
O2 O 0.2500(3) 0.88445(7) 0.70422(18) 0.0262(4) Uani 1 1 d . . . . .
O3 O 0.2675(2) 0.90732(7) 0.22718(17) 0.0180(4) Uani 1 1 d . . . . .
O4 O 0.2338(2) 0.99695(7) 0.13037(16) 0.0175(4) Uani 1 1 d . . . . .
O5 O 0.7061(3) 1.34257(8) 0.3573(2) 0.0266(4) Uani 1 1 d . . . . .
O6 O 0.9030(3) 1.27154(9) 0.4589(2) 0.0361(5) Uani 1 1 d . . . . .
N1 N 0.3003(3) 1.18459(9) 0.4805(2) 0.0159(4) Uani 1 1 d . . . . .
C1 C 0.2485(3) 0.94015(11) 0.7246(2) 0.0160(5) Uani 1 1 d . . . . .
C2 C 0.2390(3) 0.98148(10) 0.6046(2) 0.0137(5) Uani 1 1 d . . . . .
C3 C 0.2547(3) 0.95662(10) 0.4815(2) 0.0147(5) Uani 1 1 d . . . . .
H3 H 0.2757 0.9143 0.4754 0.018 Uiso 1 1 calc R U . . .
C4 C 0.2402(3) 0.99262(10) 0.3673(2) 0.0144(5) Uani 1 1 d . . . . .
C5 C 0.2480(3) 0.96433(10) 0.2353(2) 0.0146(5) Uani 1 1 d . . . . .
C6 C 0.2091(3) 1.05473(10) 0.3768(2) 0.0154(5) Uani 1 1 d . . . . .
H6 H 0.2002 1.0798 0.2993 0.018 Uiso 1 1 calc R U . . .
C7 C 0.1910(3) 1.07992(10) 0.4985(2) 0.0147(4) Uani 1 1 d . . . . .
C8 C 0.2053(3) 1.04327(10) 0.6123(2) 0.0154(5) Uani 1 1 d . . . . .
H8 H 0.1921 1.0606 0.6958 0.018 Uiso 1 1 calc R U . . .
C9 C 0.1468(3) 1.14660(11) 0.5073(3) 0.0183(5) Uani 1 1 d . . . . .
H9A H 0.0329 1.1563 0.4403 0.022 Uiso 1 1 calc R U . . .
H9B H 0.1259 1.1559 0.5986 0.022 Uiso 1 1 calc R U . . .
C10 C 0.2685(3) 1.22796(11) 0.3856(3) 0.0191(5) Uani 1 1 d . . . . .
H10 H 0.1479 1.2339 0.3334 0.023 Uiso 1 1 calc R U . . .
C11 C 0.4108(3) 1.26409(12) 0.3636(3) 0.0214(5) Uani 1 1 d . . . . .
H11 H 0.3871 1.2963 0.2999 0.026 Uiso 1 1 calc R U . . .
C12 C 0.5870(3) 1.25311(11) 0.4346(3) 0.0183(5) Uani 1 1 d . . . . .
C13 C 0.6153(4) 1.20735(12) 0.5298(3) 0.0244(6) Uani 1 1 d . . . . .
H13 H 0.7360 1.1989 0.5792 0.029 Uiso 1 1 calc R U . . .
C14 C 0.4703(4) 1.17405(12) 0.5537(3) 0.0234(6) Uani 1 1 d . . . . .
H14 H 0.4899 1.1436 0.6218 0.028 Uiso 1 1 calc R U . . .
C15 C 0.7468(3) 1.29221(11) 0.4147(3) 0.0214(5) Uani 1 1 d . . . . .
O1W O 0.5412(2) 0.93135(7) 1.06214(18) 0.0215(4) Uani 1 1 d . . . . .
H1WA H 0.5913 0.9635 1.0959 0.026 Uiso 1 1 d R U . . .
H1WB H 0.6146 0.9042 1.0979 0.026 Uiso 1 1 d R U . . .
O2W O -0.0172(2) 0.90685(7) 0.96824(18) 0.0195(4) Uani 1 1 d . . . . .
H2WA H -0.0867 0.9359 0.9380 0.023 Uiso 1 1 d R U . . .
H2WB H -0.0441 0.8884 1.0340 0.023 Uiso 1 1 d R U . . .
O3W O 0.2899(2) 0.83565(7) 0.94393(18) 0.0175(4) Uani 1 1 d . . . . .
H3WA H 0.3959 0.8220 0.9740 0.026 Uiso 1 1 d R U . . .
H3WB H 0.2712 0.8359 0.8590 0.026 Uiso 1 1 d R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 O1 2.0286(16) . ?
Ni1 O3W 2.0347(16) . ?
Ni1 O1W 2.0420(17) . ?
Ni1 O2W 2.0648(17) . ?
Ni1 O4 2.0827(17) 1_556 ?
Ni1 O3 2.1559(17) 1_556 ?
Ni1 C5 2.448(2) 1_556 ?
O1 C1 1.273(3) . ?
O2 C1 1.246(3) . ?
O3 C5 1.270(3) . ?
O3 Ni1 2.1559(17) 1_554 ?
O4 C5 1.267(3) . ?
O4 Ni1 2.0827(17) 1_554 ?
O5 C15 1.260(3) . ?
O6 C15 1.243(3) . ?
N1 C10 1.339(3) . ?
N1 C14 1.345(3) . ?
N1 C9 1.490(3) . ?
C1 C2 1.507(3) . ?
C2 C3 1.388(3) . ?
C2 C8 1.391(3) . ?
C3 C4 1.387(3) . ?
C4 C6 1.396(3) . ?
C4 C5 1.486(3) . ?
C5 Ni1 2.448(2) 1_554 ?
C6 C7 1.383(3) . ?
C7 C8 1.391(3) . ?
C7 C9 1.514(3) . ?
C10 C11 1.383(4) . ?
C11 C12 1.378(3) . ?
C12 C13 1.380(4) . ?
C12 C15 1.519(3) . ?
C13 C14 1.371(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Ni1 O3W 97.10(7) . . ?
O1 Ni1 O1W 90.01(7) . . ?
O3W Ni1 O1W 90.90(7) . . ?
O1 Ni1 O2W 90.95(7) . . ?
O3W Ni1 O2W 87.36(7) . . ?
O1W Ni1 O2W 178.11(7) . . ?
O1 Ni1 O4 96.37(6) . 1_556 ?
O3W Ni1 O4 166.50(7) . 1_556 ?
O1W Ni1 O4 90.01(7) . 1_556 ?
O2W Ni1 O4 91.50(7) . 1_556 ?
O1 Ni1 O3 158.74(6) . 1_556 ?
O3W Ni1 O3 104.16(7) . 1_556 ?
O1W Ni1 O3 89.22(7) . 1_556 ?
O2W Ni1 O3 90.48(7) . 1_556 ?
O4 Ni1 O3 62.38(6) 1_556 1_556 ?
O1 Ni1 C5 127.53(7) . 1_556 ?
O3W Ni1 C5 135.37(7) . 1_556 ?
O1W Ni1 C5 89.20(8) . 1_556 ?
O2W Ni1 C5 91.51(7) . 1_556 ?
O4 Ni1 C5 31.17(7) 1_556 1_556 ?
O3 Ni1 C5 31.21(7) 1_556 1_556 ?
C1 O1 Ni1 125.04(15) . . ?
C5 O3 Ni1 87.21(14) . 1_554 ?
C5 O4 Ni1 90.55(14) . 1_554 ?
C10 N1 C14 121.3(2) . . ?
C10 N1 C9 120.5(2) . . ?
C14 N1 C9 118.3(2) . . ?
O2 C1 O1 125.5(2) . . ?
O2 C1 C2 117.6(2) . . ?
O1 C1 C2 116.9(2) . . ?
C3 C2 C8 119.2(2) . . ?
C3 C2 C1 119.0(2) . . ?
C8 C2 C1 121.7(2) . . ?
C4 C3 C2 121.0(2) . . ?
C3 C4 C6 119.3(2) . . ?
C3 C4 C5 119.8(2) . . ?
C6 C4 C5 120.9(2) . . ?
O4 C5 O3 119.8(2) . . ?
O4 C5 C4 120.1(2) . . ?
O3 C5 C4 120.1(2) . . ?
O4 C5 Ni1 58.28(12) . 1_554 ?
O3 C5 Ni1 61.58(12) . 1_554 ?
C4 C5 Ni1 178.28(17) . 1_554 ?
C7 C6 C4 120.3(2) . . ?
C6 C7 C8 119.9(2) . . ?
C6 C7 C9 120.4(2) . . ?
C8 C7 C9 119.7(2) . . ?
C2 C8 C7 120.4(2) . . ?
N1 C9 C7 110.5(2) . . ?
N1 C10 C11 120.2(2) . . ?
C12 C11 C10 119.7(2) . . ?
C11 C12 C13 118.6(2) . . ?
C11 C12 C15 121.3(2) . . ?
C13 C12 C15 120.0(2) . . ?
C14 C13 C12 120.4(2) . . ?
N1 C14 C13 119.8(2) . . ?
O6 C15 O5 127.2(2) . . ?
O6 C15 C12 116.5(2) . . ?
O5 C15 C12 116.3(2) . . ?

_refine_diff_density_max         0.570
_refine_diff_density_min         -0.463
_refine_diff_density_rms         0.084

_shelxl_version_number           2013-3

####################################################################### 
# 
# 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_an150a
_audit_block_doi                 10.5517/ccdc.csd.cc1jyzl1
_database_code_depnum_ccdc_archive 'CCDC 1428994'
_audit_update_record             
;
2017-02-24 deposited with the CCDC.
2017-03-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H21 Cd N O12'
_chemical_formula_sum            'C15 H21 Cd N O12'
_chemical_formula_weight         519.73

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'
Cd Cd -0.8075 1.2024 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

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

_cell_length_a                   9.0302(5)
_cell_length_b                   10.2284(5)
_cell_length_c                   11.2165(6)
_cell_angle_alpha                74.5063(14)
_cell_angle_beta                 71.6148(14)
_cell_angle_gamma                73.4060(15)
_cell_volume                     924.15(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    36479
_cell_measurement_theta_min      1.951
_cell_measurement_theta_max      28.302

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.868
_exptl_crystal_F_000             524
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    1.250
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.796
_exptl_absorpt_correction_T_max  0.922
_exptl_absorpt_process_details   'SADABS (Sheldrick 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            36479
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.951
_diffrn_reflns_theta_max         28.302
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4586
_reflns_number_gt                4424
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX2 (Bruker, 2013)'
_computing_cell_refinement       'APEX2 (Bruker, 2013)'
_computing_data_reduction        'APEX2 (Bruker, 2013)'
_computing_structure_solution    'SHELXT-2014/6 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    Diamond
_computing_publication_material  'SHELXT-2014/6 (Sheldrick, 2014)'


_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0202P)²+0.6690P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4586
_refine_ls_number_parameters     273
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0186
_refine_ls_R_factor_gt           0.0177
_refine_ls_wR_factor_ref         0.0454
_refine_ls_wR_factor_gt          0.0448
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_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
Cd1 Cd 0.18357(2) 0.10379(2) 0.10872(2) 0.01272(4) Uani 1 1 d . . . . .
O1 O 0.34917(14) 0.20557(11) 0.14463(11) 0.0203(2) Uani 1 1 d . . . . .
O2 O 0.16804(14) 0.38058(12) 0.07266(11) 0.0206(2) Uani 1 1 d . . . . .
O3 O 0.16656(13) 0.86717(11) 0.11677(11) 0.0167(2) Uani 1 1 d . . . . .
O4 O 0.36441(13) 0.89102(11) 0.17758(12) 0.0198(2) Uani 1 1 d . . . . .
O5 O 0.92118(16) 0.69891(12) 0.59714(11) 0.0247(2) Uani 1 1 d . . . . .
O6 O 0.9177(3) 0.86712(15) 0.42450(14) 0.0507(5) Uani 1 1 d . . . . .
N1 N 0.78352(14) 0.49219(12) 0.30458(12) 0.0141(2) Uani 1 1 d . . . . .
C1 C 0.28669(18) 0.33531(15) 0.11699(13) 0.0144(3) Uani 1 1 d . . . . .
C2 C 0.36570(16) 0.43281(14) 0.14285(13) 0.0117(2) Uani 1 1 d . . . . .
C3 C 0.29642(16) 0.57464(14) 0.13143(13) 0.0119(2) Uani 1 1 d . . . . .
H3 H 0.2016 0.6115 0.1028 0.014 Uiso 1 1 calc R U . . .
C4 C 0.36643(16) 0.66235(14) 0.16214(13) 0.0121(2) Uani 1 1 d . . . . .
C5 C 0.29448(17) 0.81564(14) 0.15107(13) 0.0126(2) Uani 1 1 d . . . . .
C6 C 0.50811(17) 0.60787(14) 0.20164(14) 0.0131(3) Uani 1 1 d . . . . .
H6 H 0.5548 0.6673 0.2238 0.016 Uiso 1 1 calc R U . . .
C7 C 0.58091(16) 0.46768(14) 0.20863(13) 0.0126(2) Uani 1 1 d . . . . .
C8 C 0.50806(17) 0.38071(14) 0.17967(13) 0.0128(2) Uani 1 1 d . . . . .
H8 H 0.5566 0.2845 0.1852 0.015 Uiso 1 1 calc R U . . .
C9 C 0.74081(18) 0.40450(15) 0.23993(16) 0.0178(3) Uani 1 1 d . . . . .
H9A H 0.7374 0.3119 0.2961 0.021 Uiso 1 1 calc R U . . .
H9B H 0.8249 0.3911 0.1597 0.021 Uiso 1 1 calc R U . . .
C10 C 0.73597(19) 0.47508(16) 0.43338(15) 0.0187(3) Uani 1 1 d . . . . .
H10 H 0.6754 0.4073 0.4818 0.022 Uiso 1 1 calc R U . . .
C11 C 0.77476(19) 0.55522(16) 0.49498(15) 0.0196(3) Uani 1 1 d . . . . .
H11 H 0.7437 0.5415 0.5858 0.023 Uiso 1 1 calc R U . . .
C12 C 0.86000(17) 0.65672(15) 0.42296(14) 0.0152(3) Uani 1 1 d . . . . .
C13 C 0.90579(17) 0.67278(15) 0.29048(14) 0.0157(3) Uani 1 1 d . . . . .
H13 H 0.9630 0.7421 0.2397 0.019 Uiso 1 1 calc R U . . .
C14 C 0.86798(18) 0.58777(15) 0.23270(14) 0.0160(3) Uani 1 1 d . . . . .
H14 H 0.9016 0.5968 0.1422 0.019 Uiso 1 1 calc R U . . .
C15 C 0.9039(2) 0.74822(16) 0.48756(15) 0.0193(3) Uani 1 1 d . . . . .
O1W O 0.02186(14) 0.11098(12) 0.31052(11) 0.0221(2) Uani 1 1 d . . . . .
H1WA H 0.0445 0.1623 0.3464 0.027 Uiso 1 1 d R U . . .
H1WB H 0.0104 0.0371 0.3641 0.027 Uiso 1 1 d R U . . .
O2W O 0.31386(14) 0.11277(12) -0.10100(11) 0.0208(2) Uani 1 1 d . . . . .
H2WA H 0.2970 0.0632 -0.1420 0.025 Uiso 1 1 d R U . . .
H2WB H 0.4130 0.1064 -0.1192 0.025 Uiso 1 1 d R U . . .
O3W O -0.06156(13) 0.17191(11) 0.06727(11) 0.0181(2) Uani 1 1 d . . . . .
H3WA H -0.0834 0.1635 0.0026 0.036(6) Uiso 1 1 d R . . . .
H3WB H -0.1277 0.1358 0.1295 0.034(6) Uiso 1 1 d R . . . .
O5W O 0.42594(19) 0.0863(2) 0.37815(18) 0.0670(6) Uani 1 1 d . . . . .
H5WA H 0.3469 0.0650 0.4368 0.080 Uiso 1 1 d R U . . .
H5WB H 0.3900 0.1100 0.3132 0.080 Uiso 1 1 d R U . . .
O6W O 0.73951(15) 0.02099(13) 0.25902(12) 0.0251(2) Uani 1 1 d . . . . .
H6WA H 0.7901 -0.0326 0.3112 0.030 Uiso 1 1 d R U . . .
H6WB H 0.6455 0.0418 0.3041 0.030 Uiso 1 1 d R U . . .
O4W' O 0.3109(4) -0.1466(3) 0.4520(3) 0.0373(6) Uani 0.5 1 d . . P A 1
H4WA H 0.3114 -0.1597 0.3810 0.045 Uiso 0.5 1 d R U P A 1
H4WB H 0.2123 -0.1213 0.4840 0.045 Uiso 0.5 1 d R U P A 1
O4W O 0.5490(4) 0.2313(3) 0.5418(3) 0.0446(7) Uani 0.5 1 d . . P B 2
H4WC H 0.5848 0.1661 0.5961 0.054 Uiso 0.5 1 d R U P B 2
H4WD H 0.5055 0.1919 0.5095 0.054 Uiso 0.5 1 d R U P B 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
Cd1 O1 2.2305(11) . ?
Cd1 O2W 2.2642(11) . ?
Cd1 O3W 2.2796(11) . ?
Cd1 O1W 2.2812(11) . ?
Cd1 O4 2.4222(11) 1_545 ?
Cd1 O3 2.4447(10) 1_545 ?
O1 C1 1.2799(18) . ?
O2 C1 1.2406(19) . ?
O3 C5 1.2587(18) . ?
O3 Cd1 2.4446(10) 1_565 ?
O4 C5 1.2653(17) . ?
O4 Cd1 2.4222(11) 1_565 ?
O5 C15 1.239(2) . ?
O6 C15 1.252(2) . ?
N1 C14 1.3433(19) . ?
N1 C10 1.349(2) . ?
N1 C9 1.4833(17) . ?
C1 C2 1.5098(18) . ?
C2 C8 1.3904(19) . ?
C2 C3 1.3947(19) . ?
C3 C4 1.3963(18) . ?
C3 H3 0.9500 . ?
C4 C6 1.4007(19) . ?
C4 C5 1.5036(18) . ?
C6 C7 1.3887(19) . ?
C6 H6 0.9500 . ?
C7 C8 1.3975(18) . ?
C7 C9 1.5137(19) . ?
C8 H8 0.9500 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.375(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.392(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.388(2) . ?
C12 C15 1.521(2) . ?
C13 C14 1.379(2) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
O1W H1WA 0.8398 . ?
O1W H1WB 0.8400 . ?
O2W H2WA 0.8398 . ?
O2W H2WB 0.8398 . ?
O3W H3WA 0.8401 . ?
O3W H3WB 0.8400 . ?
O5W H5WA 0.8400 . ?
O5W H5WB 0.8398 . ?
O6W H6WA 0.8400 . ?
O6W H6WB 0.8400 . ?
O4W' H4WA 0.8402 . ?
O4W' H4WB 0.8400 . ?
O4W H4WC 0.8400 . ?
O4W H4WD 0.8401 . ?

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 Cd1 O2W 93.49(4) . . ?
O1 Cd1 O3W 136.48(4) . . ?
O2W Cd1 O3W 92.78(4) . . ?
O1 Cd1 O1W 90.89(4) . . ?
O2W Cd1 O1W 172.16(4) . . ?
O3W Cd1 O1W 79.58(4) . . ?
O1 Cd1 O4 83.67(4) . 1_545 ?
O2W Cd1 O4 93.37(4) . 1_545 ?
O3W Cd1 O4 138.79(4) . 1_545 ?
O1W Cd1 O4 93.58(4) . 1_545 ?
O1 Cd1 O3 137.25(4) . 1_545 ?
O2W Cd1 O3 87.54(4) . 1_545 ?
O3W Cd1 O3 86.01(4) . 1_545 ?
O1W Cd1 O3 93.66(4) . 1_545 ?
O4 Cd1 O3 53.64(3) 1_545 1_545 ?
C1 O1 Cd1 103.17(9) . . ?
C5 O3 Cd1 92.06(8) . 1_565 ?
C5 O4 Cd1 92.93(9) . 1_565 ?
C14 N1 C10 121.61(13) . . ?
C14 N1 C9 118.87(13) . . ?
C10 N1 C9 119.52(13) . . ?
O2 C1 O1 123.27(13) . . ?
O2 C1 C2 120.98(13) . . ?
O1 C1 C2 115.75(13) . . ?
C8 C2 C3 119.59(12) . . ?
C8 C2 C1 119.77(12) . . ?
C3 C2 C1 120.63(13) . . ?
C2 C3 C4 119.97(13) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C6 119.76(12) . . ?
C3 C4 C5 121.24(12) . . ?
C6 C4 C5 118.99(12) . . ?
O3 C5 O4 120.95(13) . . ?
O3 C5 C4 120.31(12) . . ?
O4 C5 C4 118.74(13) . . ?
C7 C6 C4 120.54(12) . . ?
C7 C6 H6 119.7 . . ?
C4 C6 H6 119.7 . . ?
C6 C7 C8 119.04(13) . . ?
C6 C7 C9 123.21(12) . . ?
C8 C7 C9 117.67(12) . . ?
C2 C8 C7 121.02(12) . . ?
C2 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
N1 C9 C7 112.58(11) . . ?
N1 C9 H9A 109.1 . . ?
C7 C9 H9A 109.1 . . ?
N1 C9 H9B 109.1 . . ?
C7 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
N1 C10 C11 120.33(14) . . ?
N1 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C10 C11 C12 119.39(14) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
C13 C12 C11 118.91(13) . . ?
C13 C12 C15 120.17(13) . . ?
C11 C12 C15 120.92(13) . . ?
C14 C13 C12 119.83(13) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
N1 C14 C13 119.91(13) . . ?
N1 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
O5 C15 O6 126.33(15) . . ?
O5 C15 C12 117.31(14) . . ?
O6 C15 C12 116.36(14) . . ?
Cd1 O1W H1WA 112.1 . . ?
Cd1 O1W H1WB 120.5 . . ?
H1WA O1W H1WB 107.0 . . ?
Cd1 O2W H2WA 119.4 . . ?
Cd1 O2W H2WB 115.7 . . ?
H2WA O2W H2WB 108.2 . . ?
Cd1 O3W H3WA 126.5 . . ?
Cd1 O3W H3WB 109.2 . . ?
H3WA O3W H3WB 104.2 . . ?
H5WA O5W H5WB 102.1 . . ?
H6WA O6W H6WB 104.1 . . ?
H4WA O4W' H4WB 100.9 . . ?
H4WC O4W H4WD 102.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cd1 O1 C1 O2 -4.45(17) . . . . ?
Cd1 O1 C1 C2 174.99(9) . . . . ?
O2 C1 C2 C8 -173.24(13) . . . . ?
O1 C1 C2 C8 7.31(19) . . . . ?
O2 C1 C2 C3 7.4(2) . . . . ?
O1 C1 C2 C3 -172.04(13) . . . . ?
C8 C2 C3 C4 -2.7(2) . . . . ?
C1 C2 C3 C4 176.64(12) . . . . ?
C2 C3 C4 C6 1.4(2) . . . . ?
C2 C3 C4 C5 -179.89(12) . . . . ?
Cd1 O3 C5 O4 6.50(14) 1_565 . . . ?
Cd1 O3 C5 C4 -173.93(11) 1_565 . . . ?
Cd1 O4 C5 O3 -6.57(15) 1_565 . . . ?
Cd1 O4 C5 C4 173.86(11) 1_565 . . . ?
C3 C4 C5 O3 1.8(2) . . . . ?
C6 C4 C5 O3 -179.43(13) . . . . ?
C3 C4 C5 O4 -178.58(13) . . . . ?
C6 C4 C5 O4 0.1(2) . . . . ?
C3 C4 C6 C7 1.0(2) . . . . ?
C5 C4 C6 C7 -177.74(13) . . . . ?
C4 C6 C7 C8 -2.1(2) . . . . ?
C4 C6 C7 C9 174.80(14) . . . . ?
C3 C2 C8 C7 1.6(2) . . . . ?
C1 C2 C8 C7 -177.71(13) . . . . ?
C6 C7 C8 C2 0.7(2) . . . . ?
C9 C7 C8 C2 -176.30(13) . . . . ?
C14 N1 C9 C7 -90.70(16) . . . . ?
C10 N1 C9 C7 88.80(16) . . . . ?
C6 C7 C9 N1 19.8(2) . . . . ?
C8 C7 C9 N1 -163.34(13) . . . . ?
C14 N1 C10 C11 -0.7(2) . . . . ?
C9 N1 C10 C11 179.85(14) . . . . ?
N1 C10 C11 C12 1.7(2) . . . . ?
C10 C11 C12 C13 -1.0(2) . . . . ?
C10 C11 C12 C15 179.47(14) . . . . ?
C11 C12 C13 C14 -0.7(2) . . . . ?
C15 C12 C13 C14 178.87(14) . . . . ?
C10 N1 C14 C13 -1.0(2) . . . . ?
C9 N1 C14 C13 178.45(13) . . . . ?
C12 C13 C14 N1 1.7(2) . . . . ?
C13 C12 C15 O5 -151.35(15) . . . . ?
C11 C12 C15 O5 28.2(2) . . . . ?
C13 C12 C15 O6 29.2(2) . . . . ?
C11 C12 C15 O6 -151.29(18) . . . . ?

_refine_diff_density_max         0.758
_refine_diff_density_min         -0.828
_refine_diff_density_rms         0.063

_shelxl_version_number           2013-3

