# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1500926'
_audit_update_record             
;
2017-04-28 deposited with the CCDC.
2017-05-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C49 H45 Mn2 N3 O11'
_chemical_formula_weight         961.76

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_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                   11.3946(9)
_cell_length_b                   28.293(3)
_cell_length_c                   15.2096(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.511(2)
_cell_angle_gamma                90.00
_cell_volume                     4787.0(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2943
_cell_measurement_theta_min      2.335
_cell_measurement_theta_max      20.490

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1992
_exptl_absorpt_coefficient_mu    0.589
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6564
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
;

CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.

;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20028
_diffrn_reflns_av_R_equivalents  0.0783
_diffrn_reflns_av_unetI/netI     0.1076
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.33
_diffrn_reflns_theta_max         25.02
_reflns_number_total             8418
_reflns_number_gt                4259
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0327P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    none
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         8418
_refine_ls_number_parameters     592
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1093
_refine_ls_R_factor_gt           0.0531
_refine_ls_wR_factor_ref         0.1174
_refine_ls_wR_factor_gt          0.1033
_refine_ls_goodness_of_fit_ref   0.972
_refine_ls_restrained_S_all      0.972
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O5 O 0.4581(3) 0.23914(9) 0.77297(19) 0.0669(8) Uani 1 1 d . . .
O6 O 0.2916(3) 0.21785(9) 0.67471(19) 0.0631(8) Uani 1 1 d . . .
C27 C 0.3961(4) 0.21047(15) 0.7199(3) 0.0519(11) Uani 1 1 d . . .
O3 O 1.4440(3) 0.26459(9) -0.03904(17) 0.0619(8) Uani 1 1 d . . .
C14 C 1.4906(4) 0.22584(16) -0.0082(3) 0.0553(11) Uani 1 1 d . . .
C15 C 1.4189(3) 0.18125(14) -0.0340(3) 0.0494(10) Uani 1 1 d . . .
C20 C 1.3023(4) 0.18323(13) -0.0857(3) 0.0521(11) Uani 1 1 d . . .
C16 C 1.4706(4) 0.13721(16) -0.0121(3) 0.0661(13) Uani 1 1 d . . .
C17 C 1.4073(4) 0.09586(15) -0.0414(3) 0.0682(13) Uani 1 1 d . . .
C19 C 1.2384(4) 0.14203(15) -0.1123(3) 0.0567(11) Uani 1 1 d . . .
C18 C 1.2916(4) 0.09775(14) -0.0913(3) 0.0552(11) Uani 1 1 d . . .
Mn1 Mn 0.96193(5) 0.19525(2) 0.34283(4) 0.04703(19) Uani 1 1 d . . .
Mn2 Mn 0.69524(5) 0.21854(2) 0.17252(4) 0.04675(19) Uani 1 1 d . . .
N1 N 1.3567(3) 0.21480(13) 0.4267(2) 0.0622(10) Uani 1 1 d . . .
N2 N 1.0554(3) 0.10327(12) 0.5725(3) 0.0656(10) Uani 1 1 d . . .
N3 N 0.3426(4) 0.2656(2) 0.2035(3) 0.1104(17) Uani 1 1 d . . .
O1 O 0.9676(3) 0.15385(9) 0.22712(19) 0.0658(8) Uani 1 1 d . . .
O2 O 0.8145(3) 0.17611(10) 0.11705(18) 0.0680(9) Uani 1 1 d . . .
O4 O 1.5907(3) 0.22194(11) 0.04296(19) 0.0757(9) Uani 1 1 d . . .
O7 O 0.7632(2) 0.19070(8) 0.31510(15) 0.0463(7) Uani 1 1 d . . .
O8 O 0.6129(3) 0.15297(9) 0.22878(18) 0.0632(8) Uani 1 1 d . . .
O9 O 1.1624(3) 0.19870(12) 0.3720(2) 0.0839(10) Uani 1 1 d . . .
O10 O 0.9981(3) 0.13268(9) 0.4298(2) 0.0679(9) Uani 1 1 d . . .
O11 O 0.5453(3) 0.25703(11) 0.2184(2) 0.0822(10) Uani 1 1 d . . .
C1 C 1.1076(4) 0.04402(13) -0.1095(3) 0.0557(11) Uani 1 1 d . . .
C2 C 1.2226(4) 0.05388(14) -0.1256(3) 0.0577(12) Uani 1 1 d . . .
C3 C 1.2706(5) 0.02321(16) -0.1817(3) 0.0803(15) Uani 1 1 d . . .
H3 H 1.3468 0.0289 -0.1921 0.096 Uiso 1 1 calc R . .
C4 C 1.2045(6) -0.01558(17) -0.2216(4) 0.0948(18) Uani 1 1 d . . .
H4 H 1.2377 -0.0359 -0.2577 0.114 Uiso 1 1 calc R . .
C5 C 1.0919(6) -0.02398(16) -0.2085(4) 0.0902(17) Uani 1 1 d . . .
H5 H 1.0473 -0.0492 -0.2373 0.108 Uiso 1 1 calc R . .
C6 C 1.0437(5) 0.00533(15) -0.1519(3) 0.0738(14) Uani 1 1 d . . .
H6 H 0.9674 -0.0010 -0.1422 0.089 Uiso 1 1 calc R . .
C7 C 0.9093(4) 0.15434(14) 0.1464(3) 0.0521(11) Uani 1 1 d . . .
C8 C 0.9609(4) 0.12593(13) 0.0796(3) 0.0475(10) Uani 1 1 d . . .
C9 C 1.0756(4) 0.10926(13) 0.1022(3) 0.0572(12) Uani 1 1 d . . .
H9 H 1.1219 0.1154 0.1593 0.069 Uiso 1 1 calc R . .
C10 C 1.1252(4) 0.08309(14) 0.0410(3) 0.0603(12) Uani 1 1 d . . .
H10 H 1.2041 0.0725 0.0578 0.072 Uiso 1 1 calc R . .
C11 C 1.0574(4) 0.07276(13) -0.0451(3) 0.0507(11) Uani 1 1 d . . .
C12 C 0.9405(4) 0.08866(15) -0.0660(3) 0.0643(12) Uani 1 1 d . . .
H12 H 0.8925 0.0817 -0.1222 0.077 Uiso 1 1 calc R . .
C13 C 0.8920(4) 0.11531(14) -0.0041(3) 0.0636(12) Uani 1 1 d . . .
H13 H 0.8129 0.1258 -0.0199 0.076 Uiso 1 1 calc R . .
H16 H 1.5482 0.1351 0.0227 0.076 Uiso 1 1 d R . .
H17 H 1.4436 0.0667 -0.0272 0.076 Uiso 1 1 d R . .
H19 H 1.1591 0.1439 -0.1447 0.076 Uiso 1 1 d R . .
H20 H 1.2662 0.2123 -0.1020 0.076 Uiso 1 1 d R . .
C21 C 0.6762(3) 0.02469(13) 0.5925(3) 0.0487(10) Uani 1 1 d . . .
C22 C 0.6320(3) 0.03340(12) 0.6701(3) 0.0456(10) Uani 1 1 d . . .
C23 C 0.6460(4) -0.00159(15) 0.7366(3) 0.0619(12) Uani 1 1 d . . .
H23 H 0.6182 0.0040 0.7888 0.074 Uiso 1 1 calc R . .
C24 C 0.7000(4) -0.04403(15) 0.7261(4) 0.0735(14) Uani 1 1 d . . .
H24 H 0.7072 -0.0670 0.7707 0.088 Uiso 1 1 calc R . .
C25 C 0.7432(4) -0.05275(15) 0.6503(4) 0.0721(14) Uani 1 1 d . . .
H25 H 0.7808 -0.0813 0.6439 0.087 Uiso 1 1 calc R . .
C26 C 0.7307(4) -0.01906(14) 0.5836(3) 0.0645(13) Uani 1 1 d . . .
H26 H 0.7588 -0.0254 0.5318 0.077 Uiso 1 1 calc R . .
C28 C 0.4528(3) 0.16352(12) 0.7080(3) 0.0430(10) Uani 1 1 d . . .
C29 C 0.5490(4) 0.14729(14) 0.7727(3) 0.0547(11) Uani 1 1 d . . .
H29 H 0.5764 0.1650 0.8246 0.066 Uiso 1 1 calc R . .
C30 C 0.6053(4) 0.10491(14) 0.7613(3) 0.0540(11) Uani 1 1 d . . .
H30 H 0.6688 0.0942 0.8061 0.065 Uiso 1 1 calc R . .
C31 C 0.5673(3) 0.07823(13) 0.6831(3) 0.0444(10) Uani 1 1 d . . .
C32 C 0.4706(4) 0.09448(13) 0.6183(3) 0.0527(11) Uani 1 1 d . . .
H32 H 0.4444 0.0772 0.5657 0.063 Uiso 1 1 calc R . .
C33 C 0.4129(3) 0.13611(13) 0.6313(3) 0.0505(11) Uani 1 1 d . . .
H33 H 0.3464 0.1459 0.5882 0.061 Uiso 1 1 calc R . .
C34 C 0.6849(4) 0.15769(14) 0.3012(3) 0.0484(10) Uani 1 1 d . . .
C35 C 0.6791(3) 0.12424(13) 0.3783(3) 0.0451(10) Uani 1 1 d . . .
C36 C 0.7327(3) 0.13593(13) 0.4669(3) 0.0499(11) Uani 1 1 d . . .
H36 H 0.7715 0.1649 0.4795 0.060 Uiso 1 1 calc R . .
C37 C 0.7286(4) 0.10457(13) 0.5365(3) 0.0509(11) Uani 1 1 d . . .
H37 H 0.7635 0.1129 0.5955 0.061 Uiso 1 1 calc R . .
C38 C 0.6722(3) 0.06054(13) 0.5183(3) 0.0479(10) Uani 1 1 d . . .
C39 C 0.6168(4) 0.04968(13) 0.4298(3) 0.0537(11) Uani 1 1 d . . .
H39 H 0.5779 0.0208 0.4169 0.064 Uiso 1 1 calc R . .
C40 C 0.6188(4) 0.08130(14) 0.3607(3) 0.0529(11) Uani 1 1 d . . .
H40 H 0.5796 0.0738 0.3021 0.064 Uiso 1 1 calc R . .
C41 C 1.2425(4) 0.22297(17) 0.4182(3) 0.0696(13) Uani 1 1 d . . .
H41 H 1.2199 0.2487 0.4488 0.084 Uiso 1 1 calc R . .
C42 C 1.3992(5) 0.17550(17) 0.3817(4) 0.1033(18) Uani 1 1 d . . .
H42A H 1.4272 0.1509 0.4245 0.155 Uiso 1 1 calc R . .
H42B H 1.4639 0.1858 0.3551 0.155 Uiso 1 1 calc R . .
H42C H 1.3347 0.1637 0.3355 0.155 Uiso 1 1 calc R . .
C43 C 1.4472(5) 0.24276(19) 0.4862(4) 0.121(2) Uani 1 1 d . . .
H43A H 1.4953 0.2592 0.4514 0.181 Uiso 1 1 calc R . .
H43B H 1.4977 0.2223 0.5287 0.181 Uiso 1 1 calc R . .
H43C H 1.4087 0.2653 0.5179 0.181 Uiso 1 1 calc R . .
C44 C 1.0426(4) 0.13764(15) 0.5111(4) 0.0673(13) Uani 1 1 d . . .
H44 H 1.0691 0.1677 0.5309 0.081 Uiso 1 1 calc R . .
C45 C 1.0212(5) 0.05564(14) 0.5468(3) 0.0920(17) Uani 1 1 d . . .
H45A H 1.0007 0.0534 0.4823 0.138 Uiso 1 1 calc R . .
H45B H 0.9529 0.0469 0.5707 0.138 Uiso 1 1 calc R . .
H45C H 1.0870 0.0348 0.5701 0.138 Uiso 1 1 calc R . .
C46 C 1.1070(5) 0.11250(18) 0.6678(3) 0.1039(19) Uani 1 1 d . . .
H46A H 1.1780 0.0937 0.6870 0.156 Uiso 1 1 calc R . .
H46B H 1.0493 0.1045 0.7030 0.156 Uiso 1 1 calc R . .
H46C H 1.1275 0.1454 0.6759 0.156 Uiso 1 1 calc R . .
C47 C 0.4421(6) 0.2436(2) 0.1906(4) 0.0968(18) Uani 1 1 d . . .
H47 H 0.4314 0.2157 0.1575 0.116 Uiso 1 1 calc R . .
C48 C 0.3564(7) 0.3086(3) 0.2603(6) 0.166(3) Uani 1 1 d . . .
H48A H 0.4380 0.3110 0.2936 0.248 Uiso 1 1 calc R . .
H48B H 0.3034 0.3067 0.3015 0.248 Uiso 1 1 calc R . .
H48C H 0.3366 0.3359 0.2227 0.248 Uiso 1 1 calc R . .
C49 C 0.2260(6) 0.2478(4) 0.1655(4) 0.215(5) Uani 1 1 d . . .
H49A H 0.1824 0.2706 0.1244 0.322 Uiso 1 1 calc R . .
H49B H 0.1839 0.2417 0.2126 0.322 Uiso 1 1 calc R . .
H49C H 0.2330 0.2189 0.1338 0.322 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O5 C27 1.250(4) . ?
O5 Mn1 2.134(3) 4_566 ?
O6 C27 1.256(5) . ?
O6 Mn2 2.105(3) 4_566 ?
C27 C28 1.505(5) . ?
O3 C14 1.263(4) . ?
O3 Mn1 2.173(3) 4_665 ?
C14 O4 1.238(5) . ?
C14 C15 1.508(5) . ?
C15 C16 1.388(5) . ?
C15 C20 1.391(5) . ?
C20 C19 1.388(5) . ?
C16 C17 1.396(5) . ?
C17 C18 1.373(6) . ?
C19 C18 1.398(5) . ?
C18 C2 1.501(5) . ?
Mn1 O1 2.127(3) . ?
Mn1 O5 2.134(3) 4_665 ?
Mn1 O3 2.173(3) 4_566 ?
Mn1 O10 2.195(3) . ?
Mn1 O7 2.215(3) . ?
Mn1 O9 2.233(3) . ?
Mn2 O4 2.072(3) 1_455 ?
Mn2 O6 2.105(3) 4_665 ?
Mn2 O2 2.120(3) . ?
Mn2 O11 2.261(3) . ?
Mn2 O7 2.279(2) . ?
Mn2 O8 2.324(3) . ?
N1 C41 1.299(5) . ?
N1 C42 1.444(5) . ?
N1 C43 1.451(5) . ?
N2 C44 1.334(5) . ?
N2 C45 1.434(5) . ?
N2 C46 1.465(5) . ?
N3 C47 1.345(6) . ?
N3 C49 1.421(7) . ?
N3 C48 1.481(8) . ?
O1 C7 1.262(4) . ?
O2 C7 1.240(4) . ?
O4 Mn2 2.072(3) 1_655 ?
O7 C34 1.278(4) . ?
O8 C34 1.229(4) . ?
O9 C41 1.233(5) . ?
O10 C44 1.239(5) . ?
O11 C47 1.220(6) . ?
C1 C6 1.393(5) . ?
C1 C2 1.412(5) . ?
C1 C11 1.480(5) . ?
C2 C3 1.407(5) . ?
C3 C4 1.393(6) . ?
C4 C5 1.362(7) . ?
C5 C6 1.391(6) . ?
C7 C8 1.512(5) . ?
C8 C9 1.362(5) . ?
C8 C13 1.376(5) . ?
C9 C10 1.400(5) . ?
C10 C11 1.399(5) . ?
C11 C12 1.376(5) . ?
C12 C13 1.409(5) . ?
C21 C22 1.402(5) . ?
C21 C26 1.405(5) . ?
C21 C38 1.511(5) . ?
C22 C23 1.399(5) . ?
C22 C31 1.501(5) . ?
C23 C24 1.374(5) . ?
C24 C25 1.371(6) . ?
C25 C26 1.376(5) . ?
C28 C29 1.384(5) . ?
C28 C33 1.393(5) . ?
C29 C30 1.388(5) . ?
C30 C31 1.396(5) . ?
C31 C32 1.389(5) . ?
C32 C33 1.384(5) . ?
C34 C35 1.520(5) . ?
C35 C36 1.393(5) . ?
C35 C40 1.393(5) . ?
C36 C37 1.389(5) . ?
C37 C38 1.402(5) . ?
C38 C39 1.392(5) . ?
C39 C40 1.384(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C27 O5 Mn1 146.5(3) . 4_566 ?
C27 O6 Mn2 125.5(3) . 4_566 ?
O5 C27 O6 125.5(4) . . ?
O5 C27 C28 116.9(4) . . ?
O6 C27 C28 117.5(4) . . ?
C14 O3 Mn1 130.8(3) . 4_665 ?
O4 C14 O3 124.5(4) . . ?
O4 C14 C15 117.5(4) . . ?
O3 C14 C15 118.0(4) . . ?
C16 C15 C20 118.4(4) . . ?
C16 C15 C14 120.7(4) . . ?
C20 C15 C14 120.7(4) . . ?
C19 C20 C15 120.5(4) . . ?
C15 C16 C17 120.8(4) . . ?
C18 C17 C16 120.8(4) . . ?
C20 C19 C18 120.8(4) . . ?
C17 C18 C19 118.6(4) . . ?
C17 C18 C2 121.9(4) . . ?
C19 C18 C2 119.5(4) . . ?
O1 Mn1 O5 93.91(11) . 4_665 ?
O1 Mn1 O3 176.02(12) . 4_566 ?
O5 Mn1 O3 87.78(10) 4_665 4_566 ?
O1 Mn1 O10 91.08(11) . . ?
O5 Mn1 O10 169.21(12) 4_665 . ?
O3 Mn1 O10 87.86(11) 4_566 . ?
O1 Mn1 O7 91.33(10) . . ?
O5 Mn1 O7 92.62(10) 4_665 . ?
O3 Mn1 O7 84.99(10) 4_566 . ?
O10 Mn1 O7 96.82(10) . . ?
O1 Mn1 O9 88.60(12) . . ?
O5 Mn1 O9 88.33(12) 4_665 . ?
O3 Mn1 O9 95.06(12) 4_566 . ?
O10 Mn1 O9 82.23(12) . . ?
O7 Mn1 O9 179.05(11) . . ?
O4 Mn2 O6 99.55(11) 1_455 4_665 ?
O4 Mn2 O2 86.20(12) 1_455 . ?
O6 Mn2 O2 96.50(11) 4_665 . ?
O4 Mn2 O11 87.38(13) 1_455 . ?
O6 Mn2 O11 90.58(11) 4_665 . ?
O2 Mn2 O11 171.14(12) . . ?
O4 Mn2 O7 158.06(10) 1_455 . ?
O6 Mn2 O7 102.23(10) 4_665 . ?
O2 Mn2 O7 93.90(10) . . ?
O11 Mn2 O7 89.79(11) . . ?
O4 Mn2 O8 101.09(11) 1_455 . ?
O6 Mn2 O8 158.05(11) 4_665 . ?
O2 Mn2 O8 92.24(11) . . ?
O11 Mn2 O8 83.01(11) . . ?
O7 Mn2 O8 56.97(9) . . ?
C41 N1 C42 121.4(4) . . ?
C41 N1 C43 121.8(4) . . ?
C42 N1 C43 116.7(4) . . ?
C44 N2 C45 120.8(4) . . ?
C44 N2 C46 121.5(4) . . ?
C45 N2 C46 117.7(4) . . ?
C47 N3 C49 121.3(7) . . ?
C47 N3 C48 118.7(6) . . ?
C49 N3 C48 120.0(6) . . ?
C7 O1 Mn1 134.0(3) . . ?
C7 O2 Mn2 136.2(3) . . ?
C14 O4 Mn2 149.6(3) . 1_655 ?
C34 O7 Mn1 136.3(2) . . ?
C34 O7 Mn2 90.8(2) . . ?
Mn1 O7 Mn2 106.48(10) . . ?
C34 O8 Mn2 89.9(2) . . ?
C41 O9 Mn1 137.5(3) . . ?
C44 O10 Mn1 119.5(3) . . ?
C47 O11 Mn2 118.6(4) . . ?
C6 C1 C2 119.1(4) . . ?
C6 C1 C11 120.0(4) . . ?
C2 C1 C11 120.9(4) . . ?
C3 C2 C1 118.7(4) . . ?
C3 C2 C18 118.5(4) . . ?
C1 C2 C18 122.6(4) . . ?
C4 C3 C2 120.4(5) . . ?
C5 C4 C3 120.7(5) . . ?
C4 C5 C6 119.8(5) . . ?
C5 C6 C1 121.2(5) . . ?
O2 C7 O1 126.1(4) . . ?
O2 C7 C8 117.2(4) . . ?
O1 C7 C8 116.7(4) . . ?
C9 C8 C13 118.8(4) . . ?
C9 C8 C7 120.4(4) . . ?
C13 C8 C7 120.8(4) . . ?
C8 C9 C10 121.3(4) . . ?
C9 C10 C11 120.8(4) . . ?
C12 C11 C10 117.3(4) . . ?
C12 C11 C1 121.3(4) . . ?
C10 C11 C1 121.3(4) . . ?
C11 C12 C13 121.3(4) . . ?
C8 C13 C12 120.5(4) . . ?
C22 C21 C26 118.9(4) . . ?
C22 C21 C38 123.6(3) . . ?
C26 C21 C38 117.5(4) . . ?
C23 C22 C21 118.6(4) . . ?
C23 C22 C31 119.0(4) . . ?
C21 C22 C31 122.4(3) . . ?
C24 C23 C22 121.2(4) . . ?
C25 C24 C23 120.4(4) . . ?
C24 C25 C26 119.8(4) . . ?
C25 C26 C21 121.1(4) . . ?
C29 C28 C33 118.4(3) . . ?
C29 C28 C27 120.2(4) . . ?
C33 C28 C27 121.4(4) . . ?
C28 C29 C30 121.0(4) . . ?
C29 C30 C31 120.5(4) . . ?
C32 C31 C30 118.6(3) . . ?
C32 C31 C22 121.5(4) . . ?
C30 C31 C22 119.9(3) . . ?
C33 C32 C31 120.6(4) . . ?
C32 C33 C28 121.0(4) . . ?
O8 C34 O7 122.3(4) . . ?
O8 C34 C35 119.5(4) . . ?
O7 C34 C35 118.2(4) . . ?
C36 C35 C40 119.2(4) . . ?
C36 C35 C34 121.0(4) . . ?
C40 C35 C34 119.8(4) . . ?
C35 C36 C37 120.3(4) . . ?
C36 C37 C38 120.5(4) . . ?
C39 C38 C37 118.7(4) . . ?
C39 C38 C21 120.6(4) . . ?
C37 C38 C21 120.7(4) . . ?
C40 C39 C38 120.9(4) . . ?
C39 C40 C35 120.4(4) . . ?
O9 C41 N1 124.0(5) . . ?
O10 C44 N2 125.1(4) . . ?
O11 C47 N3 125.7(6) . . ?

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.034 0.444 0.632 16 1 ' '
2 -0.035 0.556 0.368 16 1 ' '
3 0.180 0.469 0.479 35 3 ' '
4 0.153 0.635 0.353 10 1 ' '
5 0.325 0.969 0.017 36 2 ' '
6 0.347 0.135 0.147 10 1 ' '
7 0.474 0.945 0.863 14 1 ' '
8 0.537 0.057 0.134 16 1 ' '
9 0.680 0.030 0.979 35 3 ' '
10 0.653 0.865 0.853 10 1 ' '
11 0.820 0.530 0.521 34 2 ' '
12 0.847 0.365 0.647 10 1 ' '
_platon_squeeze_details          
;
;

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.497
_refine_diff_density_rms         0.066
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2
_database_code_depnum_ccdc_archive 'CCDC 1500925'
_audit_update_record             
;
2017-05-19 deposited with the CCDC.
2017-05-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H14 Cd O5'
_chemical_formula_weight         446.71

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'Pbca '

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

_cell_length_a                   17.3554(15)
_cell_length_b                   7.2747(7)
_cell_length_c                   28.732(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3627.5(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2351
_cell_measurement_theta_min      2.745
_cell_measurement_theta_max      21.691

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.636
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1776
_exptl_absorpt_coefficient_mu    1.231
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.80
_exptl_absorpt_correction_T_max  0.90
_exptl_absorpt_process_details   
;

CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.

;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3208
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_unetI/netI     0.0643
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         2.35
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3208
_reflns_number_gt                2173
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0497P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3208
_refine_ls_number_parameters     245
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0697
_refine_ls_R_factor_gt           0.0434
_refine_ls_wR_factor_ref         0.1025
_refine_ls_wR_factor_gt          0.0942
_refine_ls_goodness_of_fit_ref   0.919
_refine_ls_restrained_S_all      0.919
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cd1 Cd 0.22242(2) 0.57460(5) 0.199484(13) 0.03574(15) Uani 1 1 d . . .
O1 O 0.3506(2) 0.5762(5) 0.17558(14) 0.0468(9) Uani 1 1 d . . .
O2 O 0.28502(19) 0.3362(5) 0.15116(12) 0.0392(9) Uani 1 1 d . . .
O3 O 0.7589(2) -0.1693(5) 0.24725(12) 0.0427(9) Uani 1 1 d . . .
O4 O 0.6447(2) -0.2960(5) 0.24304(12) 0.0488(10) Uani 1 1 d . . .
O5 O 0.1116(2) 0.4432(6) 0.17355(14) 0.0518(10) Uani 1 1 d D . .
C1 C 0.3469(3) 0.4346(7) 0.15120(17) 0.0361(12) Uani 1 1 d . . .
C2 C 0.4117(3) 0.3792(6) 0.12045(16) 0.0314(12) Uani 1 1 d . . .
C3 C 0.4850(3) 0.4415(7) 0.12689(17) 0.0387(13) Uani 1 1 d . . .
H3 H 0.4952 0.5203 0.1516 0.046 Uiso 1 1 calc R . .
C4 C 0.5445(3) 0.3908(7) 0.09772(18) 0.0417(13) Uani 1 1 d . . .
H4 H 0.5941 0.4338 0.1034 0.050 Uiso 1 1 calc R . .
C5 C 0.5308(3) 0.2758(6) 0.06000(16) 0.0303(12) Uani 1 1 d . . .
C6 C 0.4560(3) 0.2161(7) 0.05294(17) 0.0388(13) Uani 1 1 d . . .
H6 H 0.4448 0.1425 0.0274 0.047 Uiso 1 1 calc R . .
C7 C 0.3982(3) 0.2638(7) 0.08300(17) 0.0390(13) Uani 1 1 d . . .
H7 H 0.3488 0.2178 0.0782 0.047 Uiso 1 1 calc R . .
C8 C 0.6948(3) -0.1939(7) 0.22623(18) 0.0380(13) Uani 1 1 d . . .
C9 C 0.6823(3) -0.1068(6) 0.17997(17) 0.0339(12) Uani 1 1 d . . .
C10 C 0.6126(3) -0.1254(7) 0.15673(17) 0.0361(12) Uani 1 1 d . . .
H10 H 0.5720 -0.1862 0.1712 0.043 Uiso 1 1 calc R . .
C11 C 0.6027(3) -0.0557(7) 0.11285(17) 0.0371(12) Uani 1 1 d . . .
H11 H 0.5554 -0.0689 0.0981 0.045 Uiso 1 1 calc R . .
C12 C 0.6628(3) 0.0351(6) 0.08996(16) 0.0302(11) Uani 1 1 d . . .
C13 C 0.7331(3) 0.0526(6) 0.11286(17) 0.0329(12) Uani 1 1 d . . .
H13 H 0.7739 0.1128 0.0984 0.039 Uiso 1 1 calc R . .
C14 C 0.7425(3) -0.0191(7) 0.15703(17) 0.0345(12) Uani 1 1 d . . .
H14 H 0.7901 -0.0085 0.1717 0.041 Uiso 1 1 calc R . .
C15 C 0.5933(3) 0.2191(6) 0.02762(16) 0.0301(11) Uani 1 1 d . . .
C16 C 0.6548(3) 0.1062(6) 0.04142(16) 0.0284(11) Uani 1 1 d . . .
C17 C 0.7098(3) 0.0561(7) 0.00897(17) 0.0343(12) Uani 1 1 d . . .
H17 H 0.7511 -0.0169 0.0181 0.041 Uiso 1 1 calc R . .
C18 C 0.7044(3) 0.1125(7) -0.03661(19) 0.0425(14) Uani 1 1 d . . .
H18 H 0.7417 0.0770 -0.0580 0.051 Uiso 1 1 calc R . .
C19 C 0.6443(3) 0.2206(7) -0.05036(18) 0.0453(14) Uani 1 1 d . . .
H19 H 0.6408 0.2594 -0.0811 0.054 Uiso 1 1 calc R . .
C20 C 0.5890(3) 0.2721(7) -0.01886(17) 0.0404(13) Uani 1 1 d . . .
H20 H 0.5478 0.3439 -0.0287 0.049 Uiso 1 1 calc R . .
H5B H 0.085(3) 0.448(6) 0.2022(11) 0.061(19) Uiso 1 1 d D . .
H5A H 0.106(5) 0.318(4) 0.164(2) 0.15(4) Uiso 1 1 d D . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cd1 O5 2.274(4) . ?
Cd1 O1 2.328(4) . ?
Cd1 O4 2.330(3) 6_566 ?
Cd1 O2 2.359(3) 8_665 ?
Cd1 O3 2.366(4) 3_655 ?
Cd1 O2 2.473(3) . ?
Cd1 O3 2.493(3) 6_566 ?
O1 C1 1.247(6) . ?
O2 C1 1.290(6) . ?
O2 Cd1 2.359(3) 8_655 ?
O3 C8 1.277(6) . ?
O3 Cd1 2.366(4) 3_645 ?
O3 Cd1 2.493(3) 6_646 ?
O4 C8 1.242(6) . ?
O4 Cd1 2.330(3) 6_646 ?
C1 C2 1.487(7) . ?
C2 C3 1.362(7) . ?
C2 C7 1.385(6) . ?
C3 C4 1.381(7) . ?
C4 C5 1.390(6) . ?
C5 C6 1.383(6) . ?
C5 C15 1.488(6) . ?
C6 C7 1.369(6) . ?
C8 C9 1.488(7) . ?
C9 C10 1.388(7) . ?
C9 C14 1.390(7) . ?
C10 C11 1.370(7) . ?
C11 C12 1.399(6) . ?
C12 C13 1.392(6) . ?
C12 C16 1.494(6) . ?
C13 C14 1.382(7) . ?
C15 C20 1.392(6) . ?
C15 C16 1.403(6) . ?
C16 C17 1.383(6) . ?
C17 C18 1.375(7) . ?
C18 C19 1.365(7) . ?
C19 C20 1.371(7) . ?

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 O1 135.55(14) . . ?
O5 Cd1 O4 84.97(14) . 6_566 ?
O1 Cd1 O4 139.46(13) . 6_566 ?
O5 Cd1 O2 95.73(13) . 8_665 ?
O1 Cd1 O2 82.79(12) . 8_665 ?
O4 Cd1 O2 93.42(12) 6_566 8_665 ?
O5 Cd1 O3 90.74(14) . 3_655 ?
O1 Cd1 O3 93.64(13) . 3_655 ?
O4 Cd1 O3 85.64(12) 6_566 3_655 ?
O2 Cd1 O3 173.35(11) 8_665 3_655 ?
O5 Cd1 O2 83.85(13) . . ?
O1 Cd1 O2 54.42(11) . . ?
O4 Cd1 O2 159.26(12) 6_566 . ?
O2 Cd1 O2 105.03(12) 8_665 . ?
O3 Cd1 O2 77.11(12) 3_655 . ?
O5 Cd1 O3 136.89(14) . 6_566 ?
O1 Cd1 O3 86.27(12) . 6_566 ?
O4 Cd1 O3 53.84(12) 6_566 6_566 ?
O2 Cd1 O3 76.85(12) 8_665 6_566 ?
O3 Cd1 O3 97.38(12) 3_655 6_566 ?
O2 Cd1 O3 139.24(11) . 6_566 ?
C1 O1 Cd1 96.4(3) . . ?
C1 O2 Cd1 119.5(3) . 8_655 ?
C1 O2 Cd1 88.6(3) . . ?
Cd1 O2 Cd1 102.19(12) 8_655 . ?
C8 O3 Cd1 122.0(3) . 3_645 ?
C8 O3 Cd1 88.0(3) . 6_646 ?
Cd1 O3 Cd1 101.43(13) 3_645 6_646 ?
C8 O4 Cd1 96.4(3) . 6_646 ?
O1 C1 O2 120.1(5) . . ?
O1 C1 C2 121.2(5) . . ?
O2 C1 C2 118.6(5) . . ?
C3 C2 C7 117.8(5) . . ?
C3 C2 C1 122.4(5) . . ?
C7 C2 C1 119.8(4) . . ?
C2 C3 C4 121.8(5) . . ?
C3 C4 C5 120.4(5) . . ?
C6 C5 C4 117.7(4) . . ?
C6 C5 C15 120.4(4) . . ?
C4 C5 C15 121.9(4) . . ?
C7 C6 C5 121.1(5) . . ?
C6 C7 C2 121.3(5) . . ?
O4 C8 O3 120.6(5) . . ?
O4 C8 C9 120.0(5) . . ?
O3 C8 C9 119.3(5) . . ?
C10 C9 C14 118.1(5) . . ?
C10 C9 C8 121.0(5) . . ?
C14 C9 C8 120.6(5) . . ?
C11 C10 C9 121.1(5) . . ?
C10 C11 C12 120.9(5) . . ?
C13 C12 C11 118.3(4) . . ?
C13 C12 C16 119.5(4) . . ?
C11 C12 C16 122.2(4) . . ?
C14 C13 C12 120.2(5) . . ?
C13 C14 C9 121.3(5) . . ?
C20 C15 C16 118.3(4) . . ?
C20 C15 C5 118.9(4) . . ?
C16 C15 C5 122.7(4) . . ?
C17 C16 C15 119.2(4) . . ?
C17 C16 C12 118.3(4) . . ?
C15 C16 C12 122.5(4) . . ?
C18 C17 C16 121.1(5) . . ?
C19 C18 C17 120.0(5) . . ?
C18 C19 C20 120.1(5) . . ?
C19 C20 C15 121.3(5) . . ?

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 -0.025 0.250 96 10 ' '
2 0.500 -0.025 0.250 96 9 ' '
3 0.500 -0.018 0.750 96 10 ' '
4 1.000 -0.018 0.750 96 10 ' '
5 0.875 0.180 0.035 9 0 ' '
6 0.375 0.180 0.465 9 0 ' '
7 0.875 0.319 0.535 9 0 ' '
8 0.375 0.319 0.965 9 0 ' '
9 0.625 0.680 0.035 9 0 ' '
10 0.125 0.680 0.465 9 0 ' '
11 0.625 0.819 0.535 9 0 ' '
12 0.125 0.819 0.965 9 0 ' '
_platon_squeeze_details          
;
;

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.709
_refine_diff_density_min         -0.459
_refine_diff_density_rms         0.099
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_160326d
_database_code_depnum_ccdc_archive 'CCDC 1500924'
_audit_update_record             
;
2016-08-25 deposited with the CCDC.
2017-05-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H16 Mn O6'
_chemical_formula_weight         407.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/c  '

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

_cell_length_a                   17.9649(15)
_cell_length_b                   10.3101(9)
_cell_length_c                   9.4650(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.2120(10)
_cell_angle_gamma                90.00
_cell_volume                     1752.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2093
_cell_measurement_theta_min      2.922
_cell_measurement_theta_max      28.196

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             836
_exptl_absorpt_coefficient_mu    0.788
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.76542
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;

CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.

;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8526
_diffrn_reflns_av_R_equivalents  0.0693
_diffrn_reflns_av_sigmaI/netI    0.0944
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.92
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3095
_reflns_number_gt                1980
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0529P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    none
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3095
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0961
_refine_ls_R_factor_gt           0.0514
_refine_ls_wR_factor_ref         0.1161
_refine_ls_wR_factor_gt          0.1007
_refine_ls_goodness_of_fit_ref   0.958
_refine_ls_restrained_S_all      0.958
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn -0.06190(3) 0.66109(6) 0.32699(5) 0.0220(2) Uani 1 1 d . . .
O1 O 0.03948(14) 0.6928(2) 0.4523(2) 0.0249(6) Uani 1 1 d . . .
O2 O 0.06275(15) 0.5415(2) 0.6138(2) 0.0263(7) Uani 1 1 d . . .
O3 O 0.13220(15) 0.2206(3) -0.0006(2) 0.0284(7) Uani 1 1 d . . .
O4 O 0.14947(15) 0.3638(2) -0.1725(2) 0.0292(7) Uani 1 1 d . . .
O5 O -0.05876(15) 0.8620(2) 0.2449(2) 0.0267(7) Uani 1 1 d . . .
H5B H -0.0764 0.8621 0.1609 0.032 Uiso 1 1 d R . .
H5C H -0.0135 0.8857 0.2414 0.032 Uiso 1 1 d R . .
O6 O 0.01394(18) 0.6058(3) 0.1488(3) 0.0458(9) Uani 1 1 d . . .
H6B H 0.0467 0.5503 0.1735 0.055 Uiso 1 1 d R . .
H6C H 0.0342 0.6710 0.1102 0.055 Uiso 1 1 d R . .
C1 C 0.0836(2) 0.6180(3) 0.5176(4) 0.0196(9) Uani 1 1 d . . .
C2 C 0.1635(2) 0.6210(3) 0.4842(4) 0.0205(9) Uani 1 1 d . . .
C3 C 0.1887(2) 0.6835(4) 0.3637(4) 0.0312(10) Uani 1 1 d . . .
H3 H 0.1549 0.7271 0.3048 0.037 Uiso 1 1 calc R . .
C4 C 0.2626(2) 0.6814(4) 0.3311(4) 0.0346(11) Uani 1 1 d . . .
H4 H 0.2779 0.7233 0.2497 0.042 Uiso 1 1 calc R . .
C5 C 0.3153(2) 0.6190(4) 0.4155(4) 0.0254(10) Uani 1 1 d . . .
C6 C 0.2903(2) 0.5602(4) 0.5383(4) 0.0311(11) Uani 1 1 d . . .
H6 H 0.3244 0.5207 0.5998 0.037 Uiso 1 1 calc R . .
C7 C 0.2164(2) 0.5599(4) 0.5699(4) 0.0270(10) Uani 1 1 d . . .
H7 H 0.2011 0.5174 0.6510 0.032 Uiso 1 1 calc R . .
C8 C 0.1670(2) 0.3140(4) -0.0551(4) 0.0238(10) Uani 1 1 d . . .
C9 C 0.2351(2) 0.3662(4) 0.0184(4) 0.0232(9) Uani 1 1 d . . .
C10 C 0.2600(2) 0.3172(4) 0.1473(4) 0.0295(10) Uani 1 1 d . . .
H10 H 0.2367 0.2451 0.1857 0.035 Uiso 1 1 calc R . .
C11 C 0.3187(2) 0.3742(4) 0.2190(4) 0.0313(11) Uani 1 1 d . . .
H11 H 0.3337 0.3411 0.3064 0.038 Uiso 1 1 calc R . .
C12 C 0.3560(2) 0.4800(4) 0.1641(4) 0.0256(10) Uani 1 1 d . . .
C13 C 0.3348(3) 0.5223(4) 0.0307(4) 0.0417(13) Uani 1 1 d . . .
H13 H 0.3615 0.5882 -0.0123 0.050 Uiso 1 1 calc R . .
C14 C 0.2744(3) 0.4676(4) -0.0392(4) 0.0401(12) Uani 1 1 d . . .
H14 H 0.2598 0.4999 -0.1272 0.048 Uiso 1 1 calc R . .
C15 C 0.3945(2) 0.6123(4) 0.3755(4) 0.0251(10) Uani 1 1 d . . .
C16 C 0.4143(2) 0.5487(4) 0.2498(4) 0.0234(9) Uani 1 1 d . . .
C17 C 0.4880(2) 0.5512(4) 0.2094(4) 0.0337(11) Uani 1 1 d . . .
H17 H 0.5012 0.5092 0.1266 0.040 Uiso 1 1 calc R . .
C18 C 0.5420(2) 0.6140(4) 0.2881(4) 0.0370(11) Uani 1 1 d . . .
H18 H 0.5907 0.6173 0.2569 0.044 Uiso 1 1 calc R . .
C19 C 0.5236(3) 0.6721(4) 0.4136(4) 0.0396(11) Uani 1 1 d . . .
H19 H 0.5601 0.7127 0.4688 0.047 Uiso 1 1 calc R . .
C20 C 0.4506(2) 0.6701(4) 0.4576(4) 0.0326(10) Uani 1 1 d . . .
H20 H 0.4388 0.7079 0.5434 0.039 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mn1 O4 2.140(2) 3_565 ?
Mn1 O2 2.163(2) 3_566 ?
Mn1 O1 2.177(3) . ?
Mn1 O3 2.182(2) 2 ?
Mn1 O5 2.214(2) . ?
Mn1 O6 2.263(3) . ?
O1 C1 1.259(4) . ?
O2 C1 1.268(4) . ?
O2 Mn1 2.163(2) 3_566 ?
O3 C8 1.264(4) . ?
O3 Mn1 2.182(2) 2_545 ?
O4 C8 1.258(4) . ?
O4 Mn1 2.140(2) 3_565 ?
O5 H5B 0.8499 . ?
O5 H5C 0.8501 . ?
O6 H6B 0.8501 . ?
O6 H6C 0.8499 . ?
C1 C2 1.476(5) . ?
C2 C7 1.387(5) . ?
C2 C3 1.394(5) . ?
C3 C4 1.370(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.384(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.394(5) . ?
C5 C15 1.482(5) . ?
C6 C7 1.366(5) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.494(5) . ?
C9 C14 1.380(5) . ?
C9 C10 1.386(5) . ?
C10 C11 1.374(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.387(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.382(5) . ?
C12 C16 1.490(5) . ?
C13 C14 1.379(6) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C20 1.393(5) . ?
C15 C16 1.410(5) . ?
C16 C17 1.386(5) . ?
C17 C18 1.373(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.377(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.384(6) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 Mn1 O2 93.00(10) 3_565 3_566 ?
O4 Mn1 O1 169.89(10) 3_565 . ?
O2 Mn1 O1 90.81(10) 3_566 . ?
O4 Mn1 O3 96.85(10) 3_565 2 ?
O2 Mn1 O3 93.97(10) 3_566 2 ?
O1 Mn1 O3 92.21(10) . 2 ?
O4 Mn1 O5 84.03(9) 3_565 . ?
O2 Mn1 O5 174.34(9) 3_566 . ?
O1 Mn1 O5 91.34(10) . . ?
O3 Mn1 O5 91.18(9) 2 . ?
O4 Mn1 O6 84.62(11) 3_565 . ?
O2 Mn1 O6 87.57(10) 3_566 . ?
O1 Mn1 O6 86.20(11) . . ?
O3 Mn1 O6 177.80(11) 2 . ?
O5 Mn1 O6 87.35(10) . . ?
C1 O1 Mn1 133.4(2) . . ?
C1 O2 Mn1 142.3(2) . 3_566 ?
C8 O3 Mn1 145.2(2) . 2_545 ?
C8 O4 Mn1 136.2(3) . 3_565 ?
Mn1 O5 H5B 108.5 . . ?
Mn1 O5 H5C 108.3 . . ?
H5B O5 H5C 107.6 . . ?
Mn1 O6 H6B 112.9 . . ?
Mn1 O6 H6C 113.0 . . ?
H6B O6 H6C 110.5 . . ?
O1 C1 O2 122.7(4) . . ?
O1 C1 C2 119.2(3) . . ?
O2 C1 C2 118.1(3) . . ?
C7 C2 C3 117.3(4) . . ?
C7 C2 C1 121.5(3) . . ?
C3 C2 C1 121.2(3) . . ?
C4 C3 C2 120.6(4) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 122.2(4) . . ?
C3 C4 H4 118.9 . . ?
C5 C4 H4 118.9 . . ?
C4 C5 C6 117.0(4) . . ?
C4 C5 C15 121.5(4) . . ?
C6 C5 C15 121.4(4) . . ?
C7 C6 C5 121.0(4) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C2 121.8(4) . . ?
C6 C7 H7 119.1 . . ?
C2 C7 H7 119.1 . . ?
O4 C8 O3 123.6(4) . . ?
O4 C8 C9 116.8(3) . . ?
O3 C8 C9 119.5(3) . . ?
C14 C9 C10 117.7(4) . . ?
C14 C9 C8 120.7(3) . . ?
C10 C9 C8 121.6(3) . . ?
C11 C10 C9 120.6(4) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C12 121.6(4) . . ?
C10 C11 H11 119.2 . . ?
C12 C11 H11 119.2 . . ?
C13 C12 C11 117.6(4) . . ?
C13 C12 C16 121.6(4) . . ?
C11 C12 C16 120.7(3) . . ?
C14 C13 C12 120.6(4) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C9 121.6(4) . . ?
C13 C14 H14 119.2 . . ?
C9 C14 H14 119.2 . . ?
C20 C15 C16 118.5(4) . . ?
C20 C15 C5 121.6(4) . . ?
C16 C15 C5 119.9(3) . . ?
C17 C16 C15 118.9(4) . . ?
C17 C16 C12 121.5(4) . . ?
C15 C16 C12 119.5(4) . . ?
C18 C17 C16 121.8(4) . . ?
C18 C17 H17 119.1 . . ?
C16 C17 H17 119.1 . . ?
C19 C18 C17 119.6(4) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C18 C19 C20 120.0(4) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C19 C20 C15 121.1(4) . . ?
C19 C20 H20 119.4 . . ?
C15 C20 H20 119.4 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.464
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.083
