# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_p2015110923_0m
_audit_block_doi                 10.5517/ccdc.csd.cc1nlynv
_database_code_depnum_ccdc_archive 'CCDC 1537558'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C7CC01898C 2017
_audit_update_record             
;
2017-03-12 deposited with the CCDC.
2017-06-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H22 N4 O16 Tm2'
_chemical_formula_weight         1008.36

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'
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'
Tm Tm -0.3139 5.2483 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   21.8947(18)
_cell_length_b                   8.3062(7)
_cell_length_c                   23.2034(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.053(4)
_cell_angle_gamma                90.00
_cell_volume                     4155.0(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8655
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      27.79

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.612
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1936
_exptl_absorpt_coefficient_mu    4.307
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.6727
_exptl_absorpt_correction_T_max  0.7245
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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            12627
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_av_sigmaI/netI    0.0446
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.78
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3642
_reflns_number_gt                3089
_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)+(0.0143P)²+24.1072P] 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         3642
_refine_ls_number_parameters     226
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0339
_refine_ls_wR_factor_ref         0.0756
_refine_ls_wR_factor_gt          0.0717
_refine_ls_goodness_of_fit_ref   1.155
_refine_ls_restrained_S_all      1.154
_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
C1 C 0.0788(3) 0.8300(9) 0.1492(3) 0.0423(17) Uani 1 1 d . . .
H1 H 0.0734 0.7318 0.1669 0.051 Uiso 1 1 calc R . .
C2 C 0.1225(3) 0.9388(7) 0.1787(2) 0.0283(13) Uani 1 1 d . . .
C3 C 0.1279(2) 1.0874(7) 0.1515(2) 0.0233(13) Uani 1 1 d . . .
C4 C 0.1709(2) 1.2160(7) 0.1768(2) 0.0245(13) Uani 1 1 d . . .
C5 C 0.0917(3) 1.1197(8) 0.0967(2) 0.0308(14) Uani 1 1 d . . .
H5 H 0.0957 1.2188 0.0791 0.037 Uiso 1 1 calc R . .
C6 C 0.0506(3) 1.0098(8) 0.0684(2) 0.0359(16) Uani 1 1 d . . .
C7 C 0.0440(3) 0.8619(9) 0.0958(3) 0.0462(19) Uani 1 1 d . . .
H7 H 0.0158 0.7859 0.0776 0.055 Uiso 1 1 calc R . .
C8 C 0.2401(3) 0.7974(7) 0.1418(2) 0.0274(13) Uani 1 1 d . . .
C9 C 0.2192(3) 0.8508(7) 0.0796(2) 0.0268(13) Uani 1 1 d . . .
C10 C 0.1791(3) 0.7537(9) 0.0398(2) 0.0361(15) Uani 1 1 d . . .
C11 C 0.1578(3) 0.8111(9) -0.0164(2) 0.0462(19) Uani 1 1 d . . .
H11 H 0.1307 0.7490 -0.0427 0.055 Uiso 1 1 calc R . .
C12 C 0.1764(3) 0.9581(9) -0.0332(3) 0.0470(18) Uani 1 1 d . . .
H12 H 0.1617 0.9946 -0.0709 0.056 Uiso 1 1 calc R . .
C13 C 0.2169(3) 1.0544(8) 0.0050(2) 0.0331(14) Uani 1 1 d . . .
C14 C 0.2371(2) 0.9982(6) 0.06136(18) 0.0285(14) Uani 1 1 d . . .
H14 H 0.2636 1.0620 0.0876 0.034 Uiso 1 1 calc R . .
H1M H 0.1696 0.5905 0.0894 0.034 Uiso 1 1 d RD . .
H1W H 0.3540 1.0630 0.2204 0.034 Uiso 1 1 d RD . .
H2W H 0.3549 1.1795 0.2551 0.034 Uiso 1 1 d RD . .
H3W H 0.1659 0.8252 0.3471 0.034 Uiso 1 1 d RD . .
H4W H 0.2157 0.8475 0.3817 0.034 Uiso 1 1 d RD . .
N1 N 0.2350(2) 1.2035(7) -0.01813(19) 0.0371(13) Uani 1 1 d . . .
N2 N 0.0179(2) 1.0537(7) 0.0123(2) 0.0370(13) Uani 1 1 d . . .
O1 O 0.26556(19) 0.9011(5) 0.17698(15) 0.0327(10) Uani 1 1 d . . .
O2 O 0.2291(2) 0.6546(5) 0.15482(15) 0.0345(10) Uani 1 1 d . . .
O3 O 0.16951(19) 1.3528(5) 0.15388(16) 0.0381(11) Uani 1 1 d . . .
O4 O 0.21081(17) 1.1915(5) 0.22431(14) 0.0274(9) Uani 1 1 d . . .
O5 O 0.15584(17) 0.8961(5) 0.22950(15) 0.0317(9) Uani 1 1 d . . .
O6 O 0.1592(2) 0.6056(6) 0.05279(16) 0.0460(12) Uani 1 1 d D . .
O7 O 0.20216(19) 0.8593(6) 0.34520(15) 0.0431(12) Uani 1 1 d D . .
O8 O 0.34427(19) 1.0801(5) 0.25379(17) 0.0378(11) Uani 1 1 d D . .
Tm1 Tm 0.252454(11) 0.96525(3) 0.271623(9) 0.02418(10) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C7 1.362(8) . ?
C1 C2 1.404(8) . ?
C1 H1 0.9300 . ?
C2 O5 1.322(6) . ?
C2 C3 1.401(8) . ?
C3 C5 1.401(7) . ?
C3 C4 1.477(8) . ?
C4 O3 1.253(7) . ?
C4 O4 1.297(6) . ?
C4 Tm1 2.798(6) 4 ?
C5 C6 1.366(8) . ?
C5 H5 0.9300 . ?
C6 C7 1.403(9) . ?
C6 N2 1.420(7) . ?
C7 H7 0.9300 . ?
C8 O1 1.249(7) . ?
C8 O2 1.257(7) . ?
C8 C9 1.503(7) . ?
C9 C14 1.374(7) . ?
C9 C10 1.411(8) . ?
C10 O6 1.356(8) . ?
C10 C11 1.390(8) . ?
C11 C12 1.365(9) . ?
C11 H11 0.9300 . ?
C12 C13 1.392(9) . ?
C12 H12 0.9300 . ?
C13 C14 1.386(7) . ?
C13 N1 1.432(8) . ?
C14 H14 0.9300 . ?
N1 N1 1.243(10) 7_575 ?
N2 N2 1.257(10) 5_575 ?
O1 Tm1 2.326(4) . ?
O2 Tm1 2.304(4) 4_545 ?
O3 Tm1 2.398(4) 4 ?
O4 Tm1 2.285(4) . ?
O4 Tm1 2.408(4) 4 ?
O5 Tm1 2.245(4) . ?
O6 H1M 0.8494 . ?
O7 Tm1 2.358(4) . ?
O7 H3W 0.8508 . ?
O7 H4W 0.8519 . ?
O8 Tm1 2.326(4) . ?
O8 H1W 0.8491 . ?
O8 H2W 0.8574 . ?
Tm1 O2 2.304(4) 4 ?
Tm1 O3 2.398(4) 4_545 ?
Tm1 O4 2.408(4) 4_545 ?
Tm1 C4 2.798(6) 4_545 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 C1 C2 122.9(6) . . ?
C7 C1 H1 118.5 . . ?
C2 C1 H1 118.5 . . ?
O5 C2 C3 124.2(5) . . ?
O5 C2 C1 119.0(5) . . ?
C3 C2 C1 116.8(5) . . ?
C2 C3 C5 119.9(5) . . ?
C2 C3 C4 123.7(4) . . ?
C5 C3 C4 116.3(5) . . ?
O3 C4 O4 117.8(5) . . ?
O3 C4 C3 121.3(4) . . ?
O4 C4 C3 120.9(5) . . ?
O3 C4 Tm1 58.6(3) . 4 ?
O4 C4 Tm1 59.2(3) . 4 ?
C3 C4 Tm1 176.9(4) . 4 ?
C6 C5 C3 121.9(6) . . ?
C6 C5 H5 119.0 . . ?
C3 C5 H5 119.0 . . ?
C5 C6 C7 118.6(5) . . ?
C5 C6 N2 117.0(6) . . ?
C7 C6 N2 124.4(6) . . ?
C1 C7 C6 119.8(6) . . ?
C1 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
O1 C8 O2 125.1(5) . . ?
O1 C8 C9 116.8(5) . . ?
O2 C8 C9 118.0(5) . . ?
C14 C9 C10 119.1(5) . . ?
C14 C9 C8 120.2(5) . . ?
C10 C9 C8 120.7(5) . . ?
O6 C10 C11 116.9(5) . . ?
O6 C10 C9 124.1(5) . . ?
C11 C10 C9 119.1(6) . . ?
C12 C11 C10 120.5(6) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 121.4(5) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C14 C13 C12 118.0(6) . . ?
C14 C13 N1 125.6(5) . . ?
C12 C13 N1 116.4(5) . . ?
C9 C14 C13 122.0(5) . . ?
C9 C14 H14 119.0 . . ?
C13 C14 H14 119.0 . . ?
N1 N1 C13 115.6(6) 7_575 . ?
N2 N2 C6 114.1(7) 5_575 . ?
C8 O1 Tm1 131.3(4) . . ?
C8 O2 Tm1 143.7(3) . 4_545 ?
C4 O3 Tm1 94.9(3) . 4 ?
C4 O4 Tm1 133.7(4) . . ?
C4 O4 Tm1 93.2(3) . 4 ?
Tm1 O4 Tm1 130.94(14) . 4 ?
C2 O5 Tm1 130.6(4) . . ?
C10 O6 H1M 108.4 . . ?
Tm1 O7 H3W 136.0 . . ?
Tm1 O7 H4W 129.5 . . ?
H3W O7 H4W 94.4 . . ?
Tm1 O8 H1W 117.1 . . ?
Tm1 O8 H2W 128.7 . . ?
H1W O8 H2W 94.9 . . ?
O5 Tm1 O4 74.60(14) . . ?
O5 Tm1 O2 121.80(15) . 4 ?
O4 Tm1 O2 78.34(13) . 4 ?
O5 Tm1 O1 78.02(14) . . ?
O4 Tm1 O1 80.76(14) . . ?
O2 Tm1 O1 145.22(15) 4 . ?
O5 Tm1 O8 143.65(14) . . ?
O4 Tm1 O8 82.07(14) . . ?
O2 Tm1 O8 78.87(14) 4 . ?
O1 Tm1 O8 70.92(14) . . ?
O5 Tm1 O7 72.30(13) . . ?
O4 Tm1 O7 117.22(15) . . ?
O2 Tm1 O7 76.23(15) 4 . ?
O1 Tm1 O7 138.46(15) . . ?
O8 Tm1 O7 144.02(13) . . ?
O5 Tm1 O3 135.48(15) . 4_545 ?
O4 Tm1 O3 147.28(13) . 4_545 ?
O2 Tm1 O3 73.83(14) 4 4_545 ?
O1 Tm1 O3 113.68(14) . 4_545 ?
O8 Tm1 O3 76.04(15) . 4_545 ?
O7 Tm1 O3 72.34(15) . 4_545 ?
O5 Tm1 O4 93.35(14) . 4_545 ?
O4 Tm1 O4 153.91(5) . 4_545 ?
O2 Tm1 O4 126.97(12) 4 4_545 ?
O1 Tm1 O4 74.05(13) . 4_545 ?
O8 Tm1 O4 95.79(14) . 4_545 ?
O7 Tm1 O4 79.29(15) . 4_545 ?
O3 Tm1 O4 54.04(12) 4_545 4_545 ?
O5 Tm1 C4 116.48(15) . 4_545 ?
O4 Tm1 C4 166.71(15) . 4_545 ?
O2 Tm1 C4 100.03(15) 4 4_545 ?
O1 Tm1 C4 94.04(15) . 4_545 ?
O8 Tm1 C4 84.67(15) . 4_545 ?
O7 Tm1 C4 74.65(16) . 4_545 ?
O3 Tm1 C4 26.49(14) 4_545 4_545 ?
O4 Tm1 C4 27.56(13) 4_545 4_545 ?

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
C7 C1 C2 O5 -177.9(6) . . . . ?
C7 C1 C2 C3 2.0(10) . . . . ?
O5 C2 C3 C5 178.2(5) . . . . ?
C1 C2 C3 C5 -1.6(9) . . . . ?
O5 C2 C3 C4 -1.0(9) . . . . ?
C1 C2 C3 C4 179.2(6) . . . . ?
C2 C3 C4 O3 -172.5(6) . . . . ?
C5 C3 C4 O3 8.3(8) . . . . ?
C2 C3 C4 O4 6.4(9) . . . . ?
C5 C3 C4 O4 -172.9(5) . . . . ?
C2 C3 C4 Tm1 -85(7) . . . 4 ?
C5 C3 C4 Tm1 96(7) . . . 4 ?
C2 C3 C5 C6 0.1(9) . . . . ?
C4 C3 C5 C6 179.4(6) . . . . ?
C3 C5 C6 C7 1.2(10) . . . . ?
C3 C5 C6 N2 -178.0(6) . . . . ?
C2 C1 C7 C6 -0.7(11) . . . . ?
C5 C6 C7 C1 -0.9(10) . . . . ?
N2 C6 C7 C1 178.3(7) . . . . ?
O1 C8 C9 C14 10.6(8) . . . . ?
O2 C8 C9 C14 -171.4(5) . . . . ?
O1 C8 C9 C10 -166.9(6) . . . . ?
O2 C8 C9 C10 11.1(9) . . . . ?
C14 C9 C10 O6 178.9(6) . . . . ?
C8 C9 C10 O6 -3.6(10) . . . . ?
C14 C9 C10 C11 -1.3(9) . . . . ?
C8 C9 C10 C11 176.3(6) . . . . ?
O6 C10 C11 C12 -178.9(6) . . . . ?
C9 C10 C11 C12 1.2(11) . . . . ?
C10 C11 C12 C13 0.0(11) . . . . ?
C11 C12 C13 C14 -1.2(10) . . . . ?
C11 C12 C13 N1 177.8(6) . . . . ?
C10 C9 C14 C13 0.1(9) . . . . ?
C8 C9 C14 C13 -177.5(5) . . . . ?
C12 C13 C14 C9 1.2(9) . . . . ?
N1 C13 C14 C9 -177.7(6) . . . . ?
C14 C13 N1 N1 -9.4(10) . . . 7_575 ?
C12 C13 N1 N1 171.7(7) . . . 7_575 ?
C5 C6 N2 N2 178.0(7) . . . 5_575 ?
C7 C6 N2 N2 -1.2(11) . . . 5_575 ?
O2 C8 O1 Tm1 -42.8(9) . . . . ?
C9 C8 O1 Tm1 135.1(4) . . . . ?
O1 C8 O2 Tm1 -9.4(11) . . . 4_545 ?
C9 C8 O2 Tm1 172.8(4) . . . 4_545 ?
O4 C4 O3 Tm1 -2.5(5) . . . 4 ?
C3 C4 O3 Tm1 176.4(5) . . . 4 ?
O3 C4 O4 Tm1 -161.4(4) . . . . ?
C3 C4 O4 Tm1 19.7(8) . . . . ?
Tm1 C4 O4 Tm1 -163.9(5) 4 . . . ?
O3 C4 O4 Tm1 2.5(5) . . . 4 ?
C3 C4 O4 Tm1 -176.4(5) . . . 4 ?
C3 C2 O5 Tm1 -30.4(8) . . . . ?
C1 C2 O5 Tm1 149.4(5) . . . . ?
C2 O5 Tm1 O4 36.5(5) . . . . ?
C2 O5 Tm1 O2 101.9(5) . . . 4 ?
C2 O5 Tm1 O1 -47.0(5) . . . . ?
C2 O5 Tm1 O8 -15.5(6) . . . . ?
C2 O5 Tm1 O7 162.4(5) . . . . ?
C2 O5 Tm1 O3 -158.7(4) . . . 4_545 ?
C2 O5 Tm1 O4 -120.0(5) . . . 4_545 ?
C2 O5 Tm1 C4 -135.6(5) . . . 4_545 ?
C4 O4 Tm1 O5 -32.2(5) . . . . ?
Tm1 O4 Tm1 O5 169.3(2) 4 . . . ?
C4 O4 Tm1 O2 -160.2(5) . . . 4 ?
Tm1 O4 Tm1 O2 41.4(2) 4 . . 4 ?
C4 O4 Tm1 O1 47.8(5) . . . . ?
Tm1 O4 Tm1 O1 -110.7(2) 4 . . . ?
C4 O4 Tm1 O8 119.6(5) . . . . ?
Tm1 O4 Tm1 O8 -38.8(2) 4 . . . ?
C4 O4 Tm1 O7 -92.5(5) . . . . ?
Tm1 O4 Tm1 O7 109.1(2) 4 . . . ?
C4 O4 Tm1 O3 167.8(4) . . . 4_545 ?
Tm1 O4 Tm1 O3 9.3(4) 4 . . 4_545 ?
C4 O4 Tm1 O4 32.7(5) . . . 4_545 ?
Tm1 O4 Tm1 O4 -125.8(3) 4 . . 4_545 ?
C4 O4 Tm1 C4 115.6(5) . . . 4_545 ?
Tm1 O4 Tm1 C4 -42.9(7) 4 . . 4_545 ?
C8 O1 Tm1 O5 -34.8(5) . . . . ?
C8 O1 Tm1 O4 -110.8(5) . . . . ?
C8 O1 Tm1 O2 -164.5(5) . . . 4 ?
C8 O1 Tm1 O8 164.4(5) . . . . ?
C8 O1 Tm1 O7 10.2(6) . . . . ?
C8 O1 Tm1 O3 99.9(5) . . . 4_545 ?
C8 O1 Tm1 O4 62.3(5) . . . 4_545 ?
C8 O1 Tm1 C4 81.5(5) . . . 4_545 ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.837
_refine_diff_density_min         -2.151
_refine_diff_density_rms         0.150
####################################################################### 
# 
# 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_p2015102407_0m
_audit_block_doi                 10.5517/ccdc.csd.cc1nllqk
_database_code_depnum_ccdc_archive 'CCDC 1537219'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C7CC01898C 2017
_audit_update_record             
;
2017-03-10 deposited with the CCDC.
2017-06-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H18 N3 O9 Tb'
_chemical_formula_weight         567.26

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Tb Tb -0.1723 4.1537 '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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.742(2)
_cell_length_b                   8.729(2)
_cell_length_c                   27.415(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.193(10)
_cell_angle_gamma                90.00
_cell_volume                     2044.8(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8004
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      27.76

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.843
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1112
_exptl_absorpt_coefficient_mu    3.513
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.5401
_exptl_absorpt_correction_T_max  0.5704
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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            13559
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_sigmaI/netI    0.0306
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.52
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3608
_reflns_number_gt                3241
_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)+(0.0186P)²+1.7088P] 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         3608
_refine_ls_number_parameters     277
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0276
_refine_ls_R_factor_gt           0.0228
_refine_ls_wR_factor_ref         0.0554
_refine_ls_wR_factor_gt          0.0509
_refine_ls_goodness_of_fit_ref   1.162
_refine_ls_restrained_S_all      1.163
_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
C1 C 0.0422(8) 0.5795(12) 0.8428(3) 0.147(4) Uani 1 1 d . . .
H1A H 0.0105 0.6484 0.8151 0.221 Uiso 1 1 calc R . .
H1B H -0.0373 0.5763 0.8622 0.221 Uiso 1 1 calc R . .
H1C H 0.0567 0.4788 0.8304 0.221 Uiso 1 1 calc R . .
C2 C 0.1835(7) 0.6614(7) 0.92452(18) 0.0679(16) Uani 1 1 d . . .
H2A H 0.2841 0.6994 0.9411 0.102 Uiso 1 1 calc R . .
H2B H 0.1610 0.5684 0.9403 0.102 Uiso 1 1 calc R . .
H2C H 0.1048 0.7364 0.9265 0.102 Uiso 1 1 calc R . .
C3 C 0.3047(5) 0.6522(5) 0.85402(17) 0.0352(10) Uani 1 1 d . . .
H3 H 0.3958 0.6849 0.8755 0.042 Uiso 1 1 calc R . .
C4 C 0.7422(4) 0.9359(4) 0.85600(13) 0.0202(8) Uani 1 1 d . . .
C5 C 0.6564(4) 0.8142(4) 0.82479(13) 0.0217(8) Uani 1 1 d . . .
C6 C 0.8107(4) 0.8994(4) 0.90540(13) 0.0232(8) Uani 1 1 d . . .
H6 H 0.7992 0.8006 0.9169 0.028 Uiso 1 1 calc R . .
C7 C 0.8941(5) 1.0042(4) 0.93738(13) 0.0263(9) Uani 1 1 d . . .
C8 C 0.9081(5) 1.1535(4) 0.92052(15) 0.0402(11) Uani 1 1 d . . .
H8 H 0.9608 1.2273 0.9422 0.048 Uiso 1 1 calc R . .
C9 C 0.8440(5) 1.1909(5) 0.87215(14) 0.0390(11) Uani 1 1 d . . .
H9 H 0.8548 1.2906 0.8614 0.047 Uiso 1 1 calc R . .
C10 C 0.5595(4) 0.7493(4) 0.66549(13) 0.0245(8) Uani 1 1 d . . .
C11 C 0.5841(5) 0.7275(4) 0.61405(13) 0.0265(9) Uani 1 1 d . . .
C12 C 0.5365(5) 0.8405(4) 0.57891(14) 0.0297(9) Uani 1 1 d . . .
H12 H 0.4865 0.9274 0.5875 0.036 Uiso 1 1 calc R . .
C13 C 0.5623(5) 0.8260(5) 0.53114(14) 0.0352(10) Uani 1 1 d . . .
C14 C 0.6325(6) 0.6947(5) 0.51813(16) 0.0509(13) Uani 1 1 d . . .
H14 H 0.6481 0.6834 0.4858 0.061 Uiso 1 1 calc R . .
C15 C 0.6791(7) 0.5818(6) 0.55232(18) 0.0596(16) Uani 1 1 d . . .
H15 H 0.7266 0.4941 0.5432 0.071 Uiso 1 1 calc R . .
C16 C 0.6564(6) 0.5966(5) 0.60022(16) 0.0415(12) Uani 1 1 d . . .
C17 C 0.7628(4) 1.0844(4) 0.83815(13) 0.0224(8) Uani 1 1 d . . .
H3W H 1.083(3) 0.489(6) 0.733(5) 0.28(7) Uiso 1 1 d D . .
N1 N 0.9625(4) 0.9504(3) 0.98602(11) 0.0293(8) Uani 1 1 d . . .
N2 N 0.5251(5) 0.9386(4) 0.49311(13) 0.0397(9) Uani 1 1 d . . .
N3 N 0.1845(5) 0.6314(5) 0.87303(14) 0.0453(10) Uani 1 1 d . . .
O1 O 0.6630(3) 0.6787(3) 0.84019(9) 0.0317(7) Uani 1 1 d . . .
O2 O 0.5722(3) 0.8419(3) 0.78165(9) 0.0241(6) Uani 1 1 d . . .
O3 O 0.7428(3) 0.4297(3) 0.77010(10) 0.0301(6) Uani 1 1 d D . .
H1W H 0.8177 0.4372 0.7554 0.045 Uiso 1 1 d RD . .
H2W H 0.7499 0.3346 0.7750 0.045 Uiso 1 1 d RD . .
O5 O 0.3110(3) 0.6331(4) 0.80997(11) 0.0424(8) Uani 1 1 d . . .
O6 O 0.6015(3) 0.6396(3) 0.69620(9) 0.0297(6) Uani 1 1 d . . .
O7 O 0.4998(3) 0.8700(3) 0.67584(9) 0.0317(7) Uani 1 1 d . . .
O8 O 0.7145(3) 1.1246(3) 0.79096(9) 0.0258(6) Uani 1 1 d . . .
O9 O 0.7044(5) 0.4822(4) 0.63279(12) 0.0618(11) Uani 1 1 d . . .
H1M H 0.6787 0.5036 0.6581 0.093 Uiso 1 1 d R . .
O10 O 0.9842(8) 0.4853(10) 0.7217(2) 0.171(3) Uani 1 1 d D . .
H4W H 0.9699 0.5787 0.7318 0.256 Uiso 1 1 d RD . .
Tb1 Tb 0.50338(2) 0.562739(19) 0.766658(6) 0.01879(7) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N3 1.417(7) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 N3 1.438(6) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 O5 1.232(5) . ?
C3 N3 1.280(5) . ?
C3 H3 0.9300 . ?
C4 C6 1.397(5) . ?
C4 C17 1.411(5) . ?
C4 C5 1.467(5) . ?
C5 O1 1.253(4) . ?
C5 O2 1.277(4) . ?
C6 C7 1.367(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.396(5) . ?
C7 N1 1.421(4) . ?
C8 C9 1.366(5) . ?
C8 H8 0.9300 . ?
C9 C17 1.399(5) . ?
C9 H9 0.9300 . ?
C10 O7 1.235(4) . ?
C10 O6 1.276(4) . ?
C10 C11 1.483(5) . ?
C11 C12 1.380(5) . ?
C11 C16 1.396(5) . ?
C12 C13 1.381(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.382(6) . ?
C13 N2 1.419(5) . ?
C14 C15 1.362(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.375(6) . ?
C15 H15 0.9300 . ?
C16 O9 1.346(5) . ?
C17 O8 1.321(4) . ?
N1 N1 1.247(6) 3_777 ?
N2 N2 1.247(7) 3_676 ?
O1 Tb1 2.418(2) . ?
O2 Tb1 2.353(2) 2_656 ?
O2 Tb1 2.523(2) . ?
O3 Tb1 2.378(3) . ?
O3 H1W 0.8398 . ?
O3 H2W 0.8410 . ?
O5 Tb1 2.337(3) . ?
O6 Tb1 2.370(3) . ?
O7 Tb1 2.310(2) 2_656 ?
O8 Tb1 2.268(2) 2_656 ?
O9 H1M 0.7954 . ?
O10 H3W 0.850(11) . ?
O10 H4W 0.8785 . ?
Tb1 O8 2.268(2) 2_646 ?
Tb1 O7 2.310(2) 2_646 ?
Tb1 O2 2.353(2) 2_646 ?

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
N3 C1 H1A 109.5 . . ?
N3 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N3 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N3 C2 H2A 109.5 . . ?
N3 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N3 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
O5 C3 N3 126.2(4) . . ?
O5 C3 H3 116.9 . . ?
N3 C3 H3 116.9 . . ?
C6 C4 C17 119.1(3) . . ?
C6 C4 C5 117.5(3) . . ?
C17 C4 C5 123.4(3) . . ?
O1 C5 O2 117.9(3) . . ?
O1 C5 C4 120.4(3) . . ?
O2 C5 C4 121.8(3) . . ?
C7 C6 C4 122.0(3) . . ?
C7 C6 H6 119.0 . . ?
C4 C6 H6 119.0 . . ?
C6 C7 C8 119.0(3) . . ?
C6 C7 N1 116.3(3) . . ?
C8 C7 N1 124.8(3) . . ?
C9 C8 C7 119.9(4) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C8 C9 C17 122.3(4) . . ?
C8 C9 H9 118.8 . . ?
C17 C9 H9 118.8 . . ?
O7 C10 O6 124.4(3) . . ?
O7 C10 C11 118.8(3) . . ?
O6 C10 C11 116.9(3) . . ?
C12 C11 C16 118.8(4) . . ?
C12 C11 C10 119.3(3) . . ?
C16 C11 C10 121.9(3) . . ?
C13 C12 C11 120.7(4) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 119.4(4) . . ?
C12 C13 N2 125.1(4) . . ?
C14 C13 N2 115.5(4) . . ?
C15 C14 C13 120.5(4) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 120.4(4) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
O9 C16 C15 118.4(4) . . ?
O9 C16 C11 121.5(4) . . ?
C15 C16 C11 120.1(4) . . ?
O8 C17 C9 119.3(3) . . ?
O8 C17 C4 123.1(3) . . ?
C9 C17 C4 117.6(3) . . ?
N1 N1 C7 114.2(4) 3_777 . ?
N2 N2 C13 114.4(4) 3_676 . ?
C3 N3 C1 120.1(5) . . ?
C3 N3 C2 123.3(4) . . ?
C1 N3 C2 116.5(5) . . ?
C5 O1 Tb1 97.9(2) . . ?
C5 O2 Tb1 135.6(2) . 2_656 ?
C5 O2 Tb1 92.2(2) . . ?
Tb1 O2 Tb1 132.11(10) 2_656 . ?
Tb1 O3 H1W 135.4 . . ?
Tb1 O3 H2W 121.5 . . ?
H1W O3 H2W 96.5 . . ?
C3 O5 Tb1 136.0(3) . . ?
C10 O6 Tb1 130.3(2) . . ?
C10 O7 Tb1 147.7(3) . 2_656 ?
C17 O8 Tb1 131.8(2) . 2_656 ?
C16 O9 H1M 107.4 . . ?
H3W O10 H4W 92.7 . . ?
O8 Tb1 O7 121.28(10) 2_646 2_646 ?
O8 Tb1 O5 72.70(10) 2_646 . ?
O7 Tb1 O5 74.39(11) 2_646 . ?
O8 Tb1 O2 73.03(8) 2_646 2_646 ?
O7 Tb1 O2 75.23(9) 2_646 2_646 ?
O5 Tb1 O2 110.77(10) . 2_646 ?
O8 Tb1 O6 76.12(10) 2_646 . ?
O7 Tb1 O6 145.21(9) 2_646 . ?
O5 Tb1 O6 139.72(10) . . ?
O2 Tb1 O6 83.12(9) 2_646 . ?
O8 Tb1 O3 138.30(9) 2_646 . ?
O7 Tb1 O3 75.80(10) 2_646 . ?
O5 Tb1 O3 146.12(10) . . ?
O2 Tb1 O3 76.28(9) 2_646 . ?
O6 Tb1 O3 72.77(9) . . ?
O8 Tb1 O1 137.14(9) 2_646 . ?
O7 Tb1 O1 79.86(9) 2_646 . ?
O5 Tb1 O1 79.45(11) . . ?
O2 Tb1 O1 148.89(8) 2_646 . ?
O6 Tb1 O1 108.45(10) . . ?
O3 Tb1 O1 79.80(9) . . ?
O8 Tb1 O2 91.15(8) 2_646 . ?
O7 Tb1 O2 128.99(8) 2_646 . ?
O5 Tb1 O2 80.55(10) . . ?
O2 Tb1 O2 155.78(4) 2_646 . ?
O6 Tb1 O2 75.18(8) . . ?
O3 Tb1 O2 106.70(9) . . ?
O1 Tb1 O2 51.98(8) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C4 C5 O1 -9.2(6) . . . . ?
C17 C4 C5 O1 168.5(4) . . . . ?
C6 C4 C5 O2 170.1(4) . . . . ?
C17 C4 C5 O2 -12.1(6) . . . . ?
C17 C4 C6 C7 1.6(6) . . . . ?
C5 C4 C6 C7 179.4(4) . . . . ?
C4 C6 C7 C8 1.6(6) . . . . ?
C4 C6 C7 N1 -177.7(4) . . . . ?
C6 C7 C8 C9 -2.6(7) . . . . ?
N1 C7 C8 C9 176.7(4) . . . . ?
C7 C8 C9 C17 0.4(8) . . . . ?
O7 C10 C11 C12 -1.5(6) . . . . ?
O6 C10 C11 C12 178.1(4) . . . . ?
O7 C10 C11 C16 177.4(4) . . . . ?
O6 C10 C11 C16 -2.9(6) . . . . ?
C16 C11 C12 C13 -1.1(6) . . . . ?
C10 C11 C12 C13 177.9(4) . . . . ?
C11 C12 C13 C14 1.9(7) . . . . ?
C11 C12 C13 N2 -176.7(4) . . . . ?
C12 C13 C14 C15 -1.4(8) . . . . ?
N2 C13 C14 C15 177.3(5) . . . . ?
C13 C14 C15 C16 0.2(9) . . . . ?
C14 C15 C16 O9 -180.0(5) . . . . ?
C14 C15 C16 C11 0.5(9) . . . . ?
C12 C11 C16 O9 -179.6(4) . . . . ?
C10 C11 C16 O9 1.4(7) . . . . ?
C12 C11 C16 C15 -0.1(7) . . . . ?
C10 C11 C16 C15 -179.0(5) . . . . ?
C8 C9 C17 O8 -174.7(4) . . . . ?
C8 C9 C17 C4 2.8(7) . . . . ?
C6 C4 C17 O8 173.7(4) . . . . ?
C5 C4 C17 O8 -4.0(6) . . . . ?
C6 C4 C17 C9 -3.7(6) . . . . ?
C5 C4 C17 C9 178.6(4) . . . . ?
C6 C7 N1 N1 -180.0(4) . . . 3_777 ?
C8 C7 N1 N1 0.7(7) . . . 3_777 ?
C12 C13 N2 N2 4.8(8) . . . 3_676 ?
C14 C13 N2 N2 -173.8(5) . . . 3_676 ?
O5 C3 N3 C1 0.9(9) . . . . ?
O5 C3 N3 C2 -177.6(5) . . . . ?
O2 C5 O1 Tb1 2.7(4) . . . . ?
C4 C5 O1 Tb1 -177.9(3) . . . . ?
O1 C5 O2 Tb1 175.4(2) . . . 2_656 ?
C4 C5 O2 Tb1 -4.0(6) . . . 2_656 ?
O1 C5 O2 Tb1 -2.6(4) . . . . ?
C4 C5 O2 Tb1 178.1(3) . . . . ?
N3 C3 O5 Tb1 -150.0(4) . . . . ?
O7 C10 O6 Tb1 28.3(6) . . . . ?
C11 C10 O6 Tb1 -151.3(3) . . . . ?
O6 C10 O7 Tb1 40.1(7) . . . 2_656 ?
C11 C10 O7 Tb1 -140.4(4) . . . 2_656 ?
C9 C17 O8 Tb1 -144.6(3) . . . 2_656 ?
C4 C17 O8 Tb1 38.1(5) . . . 2_656 ?
C3 O5 Tb1 O8 -174.6(4) . . . 2_646 ?
C3 O5 Tb1 O7 54.7(4) . . . 2_646 ?
C3 O5 Tb1 O2 121.8(4) . . . 2_646 ?
C3 O5 Tb1 O6 -133.8(4) . . . . ?
C3 O5 Tb1 O3 25.5(5) . . . . ?
C3 O5 Tb1 O1 -27.6(4) . . . . ?
C3 O5 Tb1 O2 -80.4(4) . . . . ?
C10 O6 Tb1 O8 40.3(3) . . . 2_646 ?
C10 O6 Tb1 O7 165.8(3) . . . 2_646 ?
C10 O6 Tb1 O5 0.2(4) . . . . ?
C10 O6 Tb1 O2 114.4(3) . . . 2_646 ?
C10 O6 Tb1 O3 -167.9(3) . . . . ?
C10 O6 Tb1 O1 -95.3(3) . . . . ?
C10 O6 Tb1 O2 -54.7(3) . . . . ?
C5 O1 Tb1 O8 -37.9(3) . . . 2_646 ?
C5 O1 Tb1 O7 -163.6(2) . . . 2_646 ?
C5 O1 Tb1 O5 -87.7(2) . . . . ?
C5 O1 Tb1 O2 159.4(2) . . . 2_646 ?
C5 O1 Tb1 O6 51.4(2) . . . . ?
C5 O1 Tb1 O3 119.2(2) . . . . ?
C5 O1 Tb1 O2 -1.5(2) . . . . ?
C5 O2 Tb1 O8 157.7(2) . . . 2_646 ?
Tb1 O2 Tb1 O8 -20.41(16) 2_656 . . 2_646 ?
C5 O2 Tb1 O7 24.5(3) . . . 2_646 ?
Tb1 O2 Tb1 O7 -153.60(14) 2_656 . . 2_646 ?
C5 O2 Tb1 O5 85.4(2) . . . . ?
Tb1 O2 Tb1 O5 -92.66(16) 2_656 . . . ?
C5 O2 Tb1 O2 -154.1(2) . . . 2_646 ?
Tb1 O2 Tb1 O2 27.76(14) 2_656 . . 2_646 ?
C5 O2 Tb1 O6 -127.0(2) . . . . ?
Tb1 O2 Tb1 O6 54.91(15) 2_656 . . . ?
C5 O2 Tb1 O3 -60.5(2) . . . . ?
Tb1 O2 Tb1 O3 121.37(15) 2_656 . . . ?
C5 O2 Tb1 O1 1.5(2) . . . . ?
Tb1 O2 Tb1 O1 -176.6(2) 2_656 . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.565
_refine_diff_density_min         -0.726
_refine_diff_density_rms         0.127
####################################################################### 
# 
# 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_p2015110920shense_1_0m
_audit_block_doi                 10.5517/ccdc.csd.cc1nllsm
_database_code_depnum_ccdc_archive 'CCDC 1537221'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C7CC01898C 2017
_audit_update_record             
;
2017-03-10 deposited with the CCDC.
2017-06-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H18 Ho N3 O9'
_chemical_formula_weight         573.27

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ho Ho -0.2175 4.6783 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P1

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                   8.8304(17)
_cell_length_b                   8.8257(17)
_cell_length_c                   27.644(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.142(9)
_cell_angle_gamma                90.00
_cell_volume                     2106.2(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9987
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      27.68

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.808
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1120
_exptl_absorpt_coefficient_mu    3.809
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.7503
_exptl_absorpt_correction_T_max  0.9629
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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            12849
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_sigmaI/netI    0.0337
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.51
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3638
_reflns_number_gt                3516
_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)+(0.0239P)²+25.2624P] 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         3638
_refine_ls_number_parameters     293
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0414
_refine_ls_wR_factor_ref         0.1090
_refine_ls_wR_factor_gt          0.1083
_refine_ls_goodness_of_fit_ref   1.177
_refine_ls_restrained_S_all      1.176
_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
C1 C 0.3054(9) 0.8466(9) 0.3553(3) 0.0334(18) Uani 1 1 d . . .
H1 H 0.3947 0.8103 0.3762 0.040 Uiso 1 1 calc R . .
C2 C 0.1855(14) 0.8359(15) 0.4261(4) 0.065(3) Uani 1 1 d . . .
H2A H 0.1122 0.7568 0.4278 0.097 Uiso 1 1 calc R . .
H2B H 0.1577 0.9251 0.4421 0.097 Uiso 1 1 calc R . .
H2C H 0.2872 0.8033 0.4424 0.097 Uiso 1 1 calc R . .
C3 C 0.0469(17) 0.930(2) 0.3456(6) 0.130(8) Uani 1 1 d . . .
H3A H 0.0623 1.0349 0.3389 0.195 Uiso 1 1 calc R . .
H3B H -0.0354 0.9208 0.3632 0.195 Uiso 1 1 calc R . .
H3C H 0.0203 0.8751 0.3150 0.195 Uiso 1 1 calc R . .
C4 C 0.5593(9) 0.7531(9) 0.1644(3) 0.0252(16) Uani 1 1 d . . .
C5 C 0.5841(9) 0.7736(8) 0.1130(2) 0.0250(16) Uani 1 1 d . . .
C6 C 0.6547(12) 0.9033(9) 0.0990(3) 0.040(2) Uani 1 1 d . . .
C7 C 0.6767(14) 0.9155(12) 0.0510(3) 0.056(3) Uani 1 1 d . . .
H7 H 0.7237 1.0018 0.0416 0.068 Uiso 1 1 calc R . .
C8 C 0.6308(13) 0.8036(12) 0.0174(3) 0.052(3) Uani 1 1 d . . .
H8 H 0.6453 0.8150 -0.0148 0.063 Uiso 1 1 calc R . .
C9 C 0.5624(10) 0.6722(10) 0.0306(3) 0.0337(18) Uani 1 1 d . . .
C10 C 0.5373(9) 0.6595(9) 0.0786(3) 0.0288(17) Uani 1 1 d . . .
H10 H 0.4887 0.5736 0.0875 0.035 Uiso 1 1 calc R . .
C11 C 0.3410(8) 1.1879(8) 0.1743(2) 0.0211(14) Uani 1 1 d . . .
C12 C 0.2550(8) 1.0665(8) 0.1436(2) 0.0202(14) Uani 1 1 d . . .
C13 C 0.2354(8) 0.9183(8) 0.1621(2) 0.0215(14) Uani 1 1 d . . .
C14 C 0.1543(11) 0.8125(9) 0.1275(3) 0.038(2) Uani 1 1 d . . .
H14 H 0.1440 0.7135 0.1380 0.046 Uiso 1 1 calc R . .
C15 C 0.0909(11) 0.8495(9) 0.0798(3) 0.039(2) Uani 1 1 d . . .
H15 H 0.0375 0.7765 0.0585 0.047 Uiso 1 1 calc R . .
C16 C 0.1055(9) 0.9964(9) 0.0625(2) 0.0249(15) Uani 1 1 d . . .
C17 C 0.1876(8) 1.1005(8) 0.0944(2) 0.0221(15) Uani 1 1 d . . .
H17 H 0.1991 1.1978 0.0828 0.027 Uiso 1 1 calc R . .
H1M H 0.673(10) 0.991(10) 0.1569(19) 0.04(2) Uiso 1 1 d D . .
H1W H 0.974(9) 0.579(6) 0.261(3) 0.02(2) Uiso 1 1 d D . .
H2W H 0.940(7) 0.458(17) 0.280(9) 0.24(13) Uiso 1 1 d D . .
H3W H 0.761(8) 1.166(3) 0.280(3) 0.04(2) Uiso 1 1 d D . .
H4W H 0.823(6) 1.070(8) 0.257(3) 0.03(2) Uiso 1 1 d D . .
Ho1 Ho 0.50379(4) 0.93907(4) 0.267056(11) 0.02355(13) Uani 1 1 d . . .
N1 N 0.5242(9) 0.5599(8) -0.0068(2) 0.0392(17) Uani 1 1 d . . .
N2 N 0.0374(8) 1.0480(7) 0.0141(2) 0.0280(14) Uani 1 1 d . . .
N3 N 0.1847(9) 0.8698(9) 0.3747(3) 0.0433(18) Uani 1 1 d . . .
O1 O 0.3104(7) 0.8686(8) 0.3122(2) 0.0431(15) Uani 1 1 d . . .
O2 O 0.4983(7) 0.6345(6) 0.17514(17) 0.0304(12) Uani 1 1 d . . .
O3 O 0.3338(7) 1.3205(6) 0.15876(18) 0.0329(13) Uani 1 1 d . . .
O4 O 0.7452(6) 1.0755(6) 0.2698(2) 0.0300(12) Uani 1 1 d D . .
O5 O 0.6001(6) 0.8633(6) 0.19481(18) 0.0294(12) Uani 1 1 d . . .
O6 O 0.7033(10) 1.0169(8) 0.1310(2) 0.060(2) Uani 1 1 d D . .
O7 O 0.2821(6) 0.8787(5) 0.20872(17) 0.0249(11) Uani 1 1 d . . .
O8 O 0.4248(6) 1.1595(5) 0.21738(16) 0.0236(11) Uani 1 1 d . . .
O9 O 1.0219(15) 0.508(3) 0.2789(5) 0.176(8) Uani 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
C1 O1 1.220(10) . ?
C1 N3 1.305(11) . ?
C1 H1 0.9300 . ?
C2 N3 1.452(12) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 N3 1.413(15) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 O2 1.241(9) . ?
C4 O5 1.286(9) . ?
C4 C5 1.494(9) . ?
C5 C10 1.389(10) . ?
C5 C6 1.397(11) . ?
C6 O6 1.347(10) . ?
C6 C7 1.385(12) . ?
C7 C8 1.357(13) . ?
C7 H7 0.9300 . ?
C8 C9 1.392(12) . ?
C8 H8 0.9300 . ?
C9 C10 1.394(10) . ?
C9 N1 1.421(10) . ?
C10 H10 0.9300 . ?
C11 O3 1.244(9) . ?
C11 O8 1.287(8) . ?
C11 C12 1.474(9) . ?
C11 Ho1 2.913(7) 2_655 ?
C12 C17 1.400(9) . ?
C12 C13 1.428(9) . ?
C13 O7 1.316(8) . ?
C13 C14 1.417(10) . ?
C14 C15 1.361(11) . ?
C14 H14 0.9300 . ?
C15 C16 1.398(11) . ?
C15 H15 0.9300 . ?
C16 C17 1.370(10) . ?
C16 N2 1.419(9) . ?
C17 H17 0.9300 . ?
Ho1 O7 2.321(5) . ?
Ho1 O2 2.354(5) 2_655 ?
Ho1 O1 2.398(6) . ?
Ho1 O8 2.399(5) . ?
Ho1 O5 2.424(5) . ?
Ho1 O4 2.435(5) . ?
Ho1 O3 2.474(5) 2_645 ?
Ho1 O8 2.561(5) 2_645 ?
Ho1 C11 2.913(7) 2_645 ?
N1 N1 1.230(14) 3_665 ?
N2 N2 1.244(12) 3_575 ?
O2 Ho1 2.354(5) 2_645 ?
O3 Ho1 2.474(5) 2_655 ?
O4 H3W 0.845(10) . ?
O4 H4W 0.845(10) . ?
O6 H1M 0.847(10) . ?
O8 Ho1 2.561(5) 2_655 ?
O9 H1W 0.851(10) . ?
O9 H2W 0.850(10) . ?

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 C1 N3 125.3(8) . . ?
O1 C1 H1 117.4 . . ?
N3 C1 H1 117.4 . . ?
N3 C2 H2A 109.5 . . ?
N3 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N3 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N3 C3 H3A 109.5 . . ?
N3 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N3 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
O2 C4 O5 124.0(6) . . ?
O2 C4 C5 119.1(6) . . ?
O5 C4 C5 116.9(7) . . ?
C10 C5 C6 119.3(7) . . ?
C10 C5 C4 118.9(7) . . ?
C6 C5 C4 121.8(7) . . ?
O6 C6 C7 118.9(8) . . ?
O6 C6 C5 121.7(7) . . ?
C7 C6 C5 119.4(8) . . ?
C8 C7 C6 121.1(8) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C7 C8 C9 120.7(8) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C8 C9 C10 118.8(7) . . ?
C8 C9 N1 116.1(7) . . ?
C10 C9 N1 125.1(7) . . ?
C5 C10 C9 120.7(7) . . ?
C5 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
O3 C11 O8 118.7(6) . . ?
O3 C11 C12 120.2(6) . . ?
O8 C11 C12 121.1(6) . . ?
O3 C11 Ho1 57.3(3) . 2_655 ?
O8 C11 Ho1 61.4(3) . 2_655 ?
C12 C11 Ho1 176.8(5) . 2_655 ?
C17 C12 C13 119.0(6) . . ?
C17 C12 C11 117.8(6) . . ?
C13 C12 C11 123.2(6) . . ?
O7 C13 C14 119.7(6) . . ?
O7 C13 C12 123.8(6) . . ?
C14 C13 C12 116.5(6) . . ?
C15 C14 C13 122.8(7) . . ?
C15 C14 H14 118.6 . . ?
C13 C14 H14 118.6 . . ?
C14 C15 C16 120.4(7) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C17 C16 C15 118.4(6) . . ?
C17 C16 N2 116.9(7) . . ?
C15 C16 N2 124.6(6) . . ?
C16 C17 C12 122.8(7) . . ?
C16 C17 H17 118.6 . . ?
C12 C17 H17 118.6 . . ?
O7 Ho1 O2 120.93(19) . 2_655 ?
O7 Ho1 O1 73.33(19) . . ?
O2 Ho1 O1 74.3(2) 2_655 . ?
O7 Ho1 O8 71.78(16) . . ?
O2 Ho1 O8 75.61(16) 2_655 . ?
O1 Ho1 O8 110.8(2) . . ?
O7 Ho1 O5 75.82(18) . . ?
O2 Ho1 O5 144.65(18) 2_655 . ?
O1 Ho1 O5 140.2(2) . . ?
O8 Ho1 O5 82.08(17) . . ?
O7 Ho1 O4 137.72(18) . . ?
O2 Ho1 O4 75.4(2) 2_655 . ?
O1 Ho1 O4 145.7(2) . . ?
O8 Ho1 O4 76.37(18) . . ?
O5 Ho1 O4 72.87(18) . . ?
O7 Ho1 O3 137.37(17) . 2_645 ?
O2 Ho1 O3 80.40(17) 2_655 2_645 ?
O1 Ho1 O3 79.1(2) . 2_645 ?
O8 Ho1 O3 149.98(16) . 2_645 ?
O5 Ho1 O3 108.88(19) . 2_645 ?
O4 Ho1 O3 80.35(19) . 2_645 ?
O7 Ho1 O8 92.15(16) . 2_645 ?
O2 Ho1 O8 128.96(16) 2_655 2_645 ?
O1 Ho1 O8 80.8(2) . 2_645 ?
O8 Ho1 O8 155.42(8) . 2_645 ?
O5 Ho1 O8 75.87(16) . 2_645 ?
O4 Ho1 O8 106.74(17) . 2_645 ?
O3 Ho1 O8 51.21(15) 2_645 2_645 ?
O7 Ho1 C11 116.17(18) . 2_645 ?
O2 Ho1 C11 104.47(18) 2_655 2_645 ?
O1 Ho1 C11 79.4(2) . 2_645 ?
O8 Ho1 C11 169.08(19) . 2_645 ?
O5 Ho1 C11 92.46(18) . 2_645 ?
O4 Ho1 C11 93.01(19) . 2_645 ?
O3 Ho1 C11 25.03(17) 2_645 2_645 ?
O8 Ho1 C11 26.20(16) 2_645 2_645 ?
N1 N1 C9 114.9(8) 3_665 . ?
N2 N2 C16 115.9(8) 3_575 . ?
C1 N3 C3 120.4(9) . . ?
C1 N3 C2 122.2(8) . . ?
C3 N3 C2 117.4(9) . . ?
C1 O1 Ho1 136.6(6) . . ?
C4 O2 Ho1 147.7(5) . 2_645 ?
C11 O3 Ho1 97.7(4) . 2_655 ?
Ho1 O4 H3W 124(5) . . ?
Ho1 O4 H4W 138(5) . . ?
H3W O4 H4W 95.6(15) . . ?
C4 O5 Ho1 130.4(5) . . ?
C6 O6 H1M 104(6) . . ?
C13 O7 Ho1 131.7(4) . . ?
C11 O8 Ho1 136.8(4) . . ?
C11 O8 Ho1 92.4(4) . 2_655 ?
Ho1 O8 Ho1 130.81(18) . 2_655 ?
H1W O9 H2W 94.5(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C4 C5 C10 0.3(11) . . . . ?
O5 C4 C5 C10 -178.0(7) . . . . ?
O2 C4 C5 C6 -178.8(8) . . . . ?
O5 C4 C5 C6 2.8(11) . . . . ?
C10 C5 C6 O6 -179.5(9) . . . . ?
C4 C5 C6 O6 -0.4(14) . . . . ?
C10 C5 C6 C7 0.0(14) . . . . ?
C4 C5 C6 C7 179.1(9) . . . . ?
O6 C6 C7 C8 179.5(11) . . . . ?
C5 C6 C7 C8 0.0(17) . . . . ?
C6 C7 C8 C9 -1.0(18) . . . . ?
C7 C8 C9 C10 2.0(16) . . . . ?
C7 C8 C9 N1 -177.7(10) . . . . ?
C6 C5 C10 C9 1.1(12) . . . . ?
C4 C5 C10 C9 -178.1(7) . . . . ?
C8 C9 C10 C5 -2.0(13) . . . . ?
N1 C9 C10 C5 177.6(8) . . . . ?
O3 C11 C12 C17 10.3(11) . . . . ?
O8 C11 C12 C17 -169.6(7) . . . . ?
Ho1 C11 C12 C17 48(9) 2_655 . . . ?
O3 C11 C12 C13 -168.7(7) . . . . ?
O8 C11 C12 C13 11.5(11) . . . . ?
Ho1 C11 C12 C13 -130(8) 2_655 . . . ?
C17 C12 C13 O7 -173.9(7) . . . . ?
C11 C12 C13 O7 5.1(11) . . . . ?
C17 C12 C13 C14 3.2(11) . . . . ?
C11 C12 C13 C14 -177.9(7) . . . . ?
O7 C13 C14 C15 174.1(8) . . . . ?
C12 C13 C14 C15 -3.1(13) . . . . ?
C13 C14 C15 C16 0.8(15) . . . . ?
C14 C15 C16 C17 1.4(14) . . . . ?
C14 C15 C16 N2 -176.8(8) . . . . ?
C15 C16 C17 C12 -1.2(12) . . . . ?
N2 C16 C17 C12 177.2(7) . . . . ?
C13 C12 C17 C16 -1.2(11) . . . . ?
C11 C12 C17 C16 179.8(7) . . . . ?
C8 C9 N1 N1 174.3(11) . . . 3_665 ?
C10 C9 N1 N1 -5.4(15) . . . 3_665 ?
C17 C16 N2 N2 -179.6(9) . . . 3_575 ?
C15 C16 N2 N2 -1.4(14) . . . 3_575 ?
O1 C1 N3 C3 -2.3(17) . . . . ?
O1 C1 N3 C2 177.8(9) . . . . ?
N3 C1 O1 Ho1 149.8(7) . . . . ?
O7 Ho1 O1 C1 172.9(9) . . . . ?
O2 Ho1 O1 C1 -57.2(8) 2_655 . . . ?
O8 Ho1 O1 C1 -124.7(8) . . . . ?
O5 Ho1 O1 C1 132.3(8) . . . . ?
O4 Ho1 O1 C1 -28.5(10) . . . . ?
O3 Ho1 O1 C1 25.8(8) 2_645 . . . ?
O8 Ho1 O1 C1 77.8(9) 2_645 . . . ?
C11 Ho1 O1 C1 51.2(8) 2_645 . . . ?
O5 C4 O2 Ho1 -43.7(14) . . . 2_645 ?
C5 C4 O2 Ho1 138.0(7) . . . 2_645 ?
O8 C11 O3 Ho1 -2.5(7) . . . 2_655 ?
C12 C11 O3 Ho1 177.6(6) . . . 2_655 ?
O2 C4 O5 Ho1 -25.4(11) . . . . ?
C5 C4 O5 Ho1 152.9(5) . . . . ?
O7 Ho1 O5 C4 -42.1(6) . . . . ?
O2 Ho1 O5 C4 -166.1(5) 2_655 . . . ?
O1 Ho1 O5 C4 -2.1(8) . . . . ?
O8 Ho1 O5 C4 -115.2(6) . . . . ?
O4 Ho1 O5 C4 166.7(6) . . . . ?
O3 Ho1 O5 C4 93.6(6) 2_645 . . . ?
O8 Ho1 O5 C4 53.9(6) 2_645 . . . ?
C11 Ho1 O5 C4 74.3(6) 2_645 . . . ?
C14 C13 O7 Ho1 143.7(6) . . . . ?
C12 C13 O7 Ho1 -39.3(10) . . . . ?
O2 Ho1 O7 C13 97.5(6) 2_655 . . . ?
O1 Ho1 O7 C13 156.9(6) . . . . ?
O8 Ho1 O7 C13 37.6(6) . . . . ?
O5 Ho1 O7 C13 -48.6(6) . . . . ?
O4 Ho1 O7 C13 -5.4(7) . . . . ?
O3 Ho1 O7 C13 -151.2(5) 2_645 . . . ?
O8 Ho1 O7 C13 -123.4(6) 2_645 . . . ?
C11 Ho1 O7 C13 -134.3(6) 2_645 . . . ?
O3 C11 O8 Ho1 -175.1(5) . . . . ?
C12 C11 O8 Ho1 4.8(11) . . . . ?
Ho1 C11 O8 Ho1 -177.5(7) 2_655 . . . ?
O3 C11 O8 Ho1 2.4(7) . . . 2_655 ?
C12 C11 O8 Ho1 -177.7(6) . . . 2_655 ?
O7 Ho1 O8 C11 -21.2(7) . . . . ?
O2 Ho1 O8 C11 -151.2(7) 2_655 . . . ?
O1 Ho1 O8 C11 -84.6(7) . . . . ?
O5 Ho1 O8 C11 56.4(7) . . . . ?
O4 Ho1 O8 C11 130.6(7) . . . . ?
O3 Ho1 O8 C11 170.8(6) 2_645 . . . ?
O8 Ho1 O8 C11 30.1(7) 2_645 . . . ?
C11 Ho1 O8 C11 117.0(9) 2_645 . . . ?
O7 Ho1 O8 Ho1 162.2(3) . . . 2_655 ?
O2 Ho1 O8 Ho1 32.1(3) 2_655 . . 2_655 ?
O1 Ho1 O8 Ho1 98.8(3) . . . 2_655 ?
O5 Ho1 O8 Ho1 -120.2(3) . . . 2_655 ?
O4 Ho1 O8 Ho1 -46.0(3) . . . 2_655 ?
O3 Ho1 O8 Ho1 -5.9(6) 2_645 . . 2_655 ?
O8 Ho1 O8 Ho1 -146.5(3) 2_645 . . 2_655 ?
C11 Ho1 O8 Ho1 -59.7(10) 2_645 . . 2_655 ?

_diffrn_measured_fraction_theta_max 0.978
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.978
_refine_diff_density_max         1.004
_refine_diff_density_min         -2.545
_refine_diff_density_rms         0.156
####################################################################### 
# 
# 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_p2015110923_0m
_audit_block_doi                 10.5517/ccdc.csd.cc1nlmql
_database_code_depnum_ccdc_archive 'CCDC 1537250'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C7CC01898C 2017
_audit_update_record             
;
2017-03-10 deposited with the CCDC.
2017-06-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H22 Er2 N4 O16'
_chemical_formula_weight         1005.02

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'
Er Er -0.2586 4.9576 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   21.8947(18)
_cell_length_b                   8.3062(7)
_cell_length_c                   23.2034(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.053(4)
_cell_angle_gamma                90.00
_cell_volume                     4155.0(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8655
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      27.79

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.607
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1928
_exptl_absorpt_coefficient_mu    4.075
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.6860
_exptl_absorpt_correction_T_max  0.7921
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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            12627
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_av_sigmaI/netI    0.0445
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.78
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3642
_reflns_number_gt                3085
_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)+(0.0125P)²+24.7325P] 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         3642
_refine_ls_number_parameters     246
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0333
_refine_ls_wR_factor_ref         0.0737
_refine_ls_wR_factor_gt          0.0696
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_restrained_S_all      1.132
_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
C1 C 0.1710(2) 0.2160(7) 0.1768(2) 0.0258(12) Uani 1 1 d . . .
C2 C 0.1279(2) 0.0872(7) 0.1514(2) 0.0245(12) Uani 1 1 d . . .
C3 C 0.0918(2) 0.1198(8) 0.0967(2) 0.0322(14) Uani 1 1 d . . .
H3 H 0.0959 0.2188 0.0791 0.039 Uiso 1 1 calc R . .
C4 C 0.0506(3) 0.0098(8) 0.0684(2) 0.0373(16) Uani 1 1 d . . .
C5 C 0.0439(3) -0.1381(9) 0.0958(3) 0.0477(19) Uani 1 1 d . . .
H5 H 0.0157 -0.2141 0.0777 0.057 Uiso 1 1 calc R . .
C6 C 0.0788(3) -0.1701(8) 0.1492(3) 0.0437(17) Uani 1 1 d . . .
H6 H 0.0735 -0.2683 0.1669 0.052 Uiso 1 1 calc R . .
C7 C 0.1225(2) -0.0612(7) 0.1787(2) 0.0294(13) Uani 1 1 d . . .
C8 C 0.2600(3) 0.2973(7) 0.3582(2) 0.0286(13) Uani 1 1 d . . .
C9 C 0.2808(3) 0.3509(7) 0.4204(2) 0.0281(13) Uani 1 1 d . . .
C10 C 0.3210(3) 0.2537(8) 0.4602(2) 0.0374(15) Uani 1 1 d . . .
C11 C 0.3422(3) 0.3111(9) 0.5164(2) 0.0476(19) Uani 1 1 d . . .
H11 H 0.3693 0.2489 0.5427 0.057 Uiso 1 1 calc R . .
C12 C 0.3236(3) 0.4579(9) 0.5332(2) 0.0483(18) Uani 1 1 d . . .
H12 H 0.3383 0.4943 0.5710 0.058 Uiso 1 1 calc R . .
C13 C 0.2831(3) 0.5544(8) 0.4950(2) 0.0346(14) Uani 1 1 d . . .
C14 C 0.2628(3) 0.4987(7) 0.4386(2) 0.0298(14) Uani 1 1 d . . .
H14 H 0.2364 0.5627 0.4124 0.036 Uiso 1 1 calc R . .
Er1 Er 0.247548(11) 0.46526(3) 0.228378(9) 0.02396(10) Uani 1 1 d . . .
H1M H 0.332(3) 0.092(10) 0.4103(7) 0.08(3) Uiso 1 1 d D . .
H1W H 0.284(3) 0.349(14) 0.1183(11) 0.15(5) Uiso 1 1 d D . .
H2W H 0.3337(14) 0.324(8) 0.152(3) 0.05(2) Uiso 1 1 d D . .
H3W H 0.146(9) 0.680(6) 0.245(5) 0.32(10) Uiso 1 1 d D . .
H4W H 0.147(3) 0.564(10) 0.2801(14) 0.07(2) Uiso 1 1 d D . .
N1 N 0.0179(2) 0.0538(7) 0.0123(2) 0.0384(12) Uani 1 1 d . . .
N2 N 0.2650(2) 0.7034(7) 0.51817(19) 0.0386(13) Uani 1 1 d . . .
O1 O 0.16953(19) 0.3528(5) 0.15388(16) 0.0398(11) Uani 1 1 d . . .
O2 O 0.21077(17) 0.1914(5) 0.22433(14) 0.0287(9) Uani 1 1 d . . .
O3 O 0.2979(2) 0.3592(6) 0.15467(17) 0.0444(12) Uani 1 1 d D . .
O4 O 0.27086(19) 0.1546(5) 0.34514(15) 0.0360(10) Uani 1 1 d . . .
O5 O 0.1555(2) 0.5809(6) 0.24625(18) 0.0396(11) Uani 1 1 d D . .
O6 O 0.15584(17) -0.1037(5) 0.22953(15) 0.0332(9) Uani 1 1 d . . .
O7 O 0.23443(19) 0.4012(5) 0.32299(15) 0.0342(10) Uani 1 1 d . . .
O8 O 0.3407(2) 0.1055(6) 0.44712(17) 0.0474(12) Uani 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
C1 O1 1.253(7) . ?
C1 O2 1.296(6) . ?
C1 C2 1.479(7) . ?
C1 Er1 2.798(5) . ?
C2 C7 1.399(8) . ?
C2 C3 1.401(7) . ?
C3 C4 1.368(8) . ?
C4 C5 1.403(9) . ?
C4 N1 1.420(7) . ?
C5 C6 1.363(8) . ?
C6 C7 1.404(8) . ?
C7 O6 1.323(6) . ?
C8 O7 1.251(7) . ?
C8 O4 1.257(7) . ?
C8 C9 1.502(7) . ?
C9 C14 1.378(8) . ?
C9 C10 1.412(8) . ?
C10 O8 1.357(8) . ?
C10 C11 1.390(8) . ?
C11 C12 1.365(9) . ?
C12 C13 1.395(9) . ?
C13 C14 1.385(8) . ?
C13 N2 1.433(8) . ?
Er1 O6 2.244(4) 4 ?
Er1 O2 2.284(4) 4 ?
Er1 O4 2.303(4) 4 ?
Er1 O7 2.325(4) . ?
Er1 O5 2.334(4) . ?
Er1 O3 2.361(4) . ?
Er1 O1 2.397(4) . ?
Er1 O2 2.409(4) . ?
N1 N1 1.257(9) 5 ?
N2 N2 1.245(9) 7_566 ?
O2 Er1 2.284(4) 4_545 ?
O4 Er1 2.303(4) 4_545 ?
O6 Er1 2.244(4) 4_545 ?

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 C1 O2 117.9(5) . . ?
O1 C1 C2 121.3(4) . . ?
O2 C1 C2 120.8(5) . . ?
O1 C1 Er1 58.6(3) . . ?
O2 C1 Er1 59.3(3) . . ?
C2 C1 Er1 176.9(4) . . ?
C7 C2 C3 120.0(5) . . ?
C7 C2 C1 123.7(4) . . ?
C3 C2 C1 116.2(5) . . ?
C4 C3 C2 121.8(6) . . ?
C3 C4 C5 118.7(5) . . ?
C3 C4 N1 116.9(6) . . ?
C5 C4 N1 124.4(5) . . ?
C6 C5 C4 119.7(6) . . ?
C5 C6 C7 122.9(6) . . ?
O6 C7 C2 124.1(5) . . ?
O6 C7 C6 119.0(5) . . ?
C2 C7 C6 116.9(5) . . ?
O7 C8 O4 125.1(5) . . ?
O7 C8 C9 116.7(5) . . ?
O4 C8 C9 118.2(5) . . ?
C14 C9 C10 119.2(5) . . ?
C14 C9 C8 120.2(5) . . ?
C10 C9 C8 120.6(5) . . ?
O8 C10 C11 116.9(5) . . ?
O8 C10 C9 124.0(5) . . ?
C11 C10 C9 119.1(6) . . ?
C12 C11 C10 120.5(6) . . ?
C11 C12 C13 121.3(5) . . ?
C14 C13 C12 118.2(6) . . ?
C14 C13 N2 125.4(5) . . ?
C12 C13 N2 116.3(5) . . ?
C9 C14 C13 121.7(5) . . ?
O6 Er1 O2 74.56(14) 4 4 ?
O6 Er1 O4 121.77(15) 4 4 ?
O2 Er1 O4 78.34(13) 4 4 ?
O6 Er1 O7 78.05(14) 4 . ?
O2 Er1 O7 80.76(13) 4 . ?
O4 Er1 O7 145.19(14) 4 . ?
O6 Er1 O5 143.63(14) 4 . ?
O2 Er1 O5 82.00(15) 4 . ?
O4 Er1 O5 78.79(15) 4 . ?
O7 Er1 O5 70.95(14) . . ?
O6 Er1 O3 72.33(15) 4 . ?
O2 Er1 O3 117.21(16) 4 . ?
O4 Er1 O3 76.21(16) 4 . ?
O7 Er1 O3 138.50(15) . . ?
O5 Er1 O3 143.99(15) . . ?
O6 Er1 O1 135.50(15) 4 . ?
O2 Er1 O1 147.30(13) 4 . ?
O4 Er1 O1 73.82(14) 4 . ?
O7 Er1 O1 113.69(14) . . ?
O5 Er1 O1 76.11(15) . . ?
O3 Er1 O1 72.31(16) . . ?
O6 Er1 O2 93.39(14) 4 . ?
O2 Er1 O2 153.90(5) 4 . ?
O4 Er1 O2 126.98(12) 4 . ?
O7 Er1 O2 74.05(13) . . ?
O5 Er1 O2 95.89(15) . . ?
O3 Er1 O2 79.31(16) . . ?
O1 Er1 O2 54.05(12) . . ?
O6 Er1 C1 116.49(15) 4 . ?
O2 Er1 C1 166.76(15) 4 . ?
O4 Er1 C1 100.04(14) 4 . ?
O7 Er1 C1 94.05(15) . . ?
O5 Er1 C1 84.79(16) . . ?
O3 Er1 C1 74.62(17) . . ?
O1 Er1 C1 26.51(14) . . ?
O2 Er1 C1 27.55(13) . . ?
N1 N1 C4 114.1(7) 5 . ?
N2 N2 C13 115.5(6) 7_566 . ?
C1 O1 Er1 94.9(3) . . ?
C1 O2 Er1 133.7(4) . 4_545 ?
C1 O2 Er1 93.1(3) . . ?
Er1 O2 Er1 130.92(14) 4_545 . ?
C8 O4 Er1 143.8(3) . 4_545 ?
C7 O6 Er1 130.6(4) . 4_545 ?
C8 O7 Er1 131.3(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C7 -172.4(6) . . . . ?
O2 C1 C2 C7 6.3(8) . . . . ?
Er1 C1 C2 C7 -85(7) . . . . ?
O1 C1 C2 C3 8.4(8) . . . . ?
O2 C1 C2 C3 -172.9(5) . . . . ?
Er1 C1 C2 C3 96(7) . . . . ?
C7 C2 C3 C4 0.1(9) . . . . ?
C1 C2 C3 C4 179.4(5) . . . . ?
C2 C3 C4 C5 1.2(10) . . . . ?
C2 C3 C4 N1 -178.0(5) . . . . ?
C3 C4 C5 C6 -0.9(10) . . . . ?
N1 C4 C5 C6 178.2(6) . . . . ?
C4 C5 C6 C7 -0.6(11) . . . . ?
C3 C2 C7 O6 178.2(5) . . . . ?
C1 C2 C7 O6 -1.0(9) . . . . ?
C3 C2 C7 C6 -1.6(8) . . . . ?
C1 C2 C7 C6 179.2(6) . . . . ?
C5 C6 C7 O6 -178.0(6) . . . . ?
C5 C6 C7 C2 1.9(10) . . . . ?
O7 C8 C9 C14 10.6(8) . . . . ?
O4 C8 C9 C14 -171.4(5) . . . . ?
O7 C8 C9 C10 -166.9(6) . . . . ?
O4 C8 C9 C10 11.2(9) . . . . ?
C14 C9 C10 O8 178.9(6) . . . . ?
C8 C9 C10 O8 -3.6(10) . . . . ?
C14 C9 C10 C11 -1.2(9) . . . . ?
C8 C9 C10 C11 176.3(6) . . . . ?
O8 C10 C11 C12 -178.9(6) . . . . ?
C9 C10 C11 C12 1.2(10) . . . . ?
C10 C11 C12 C13 0.0(11) . . . . ?
C11 C12 C13 C14 -1.2(10) . . . . ?
C11 C12 C13 N2 177.8(6) . . . . ?
C10 C9 C14 C13 0.0(9) . . . . ?
C8 C9 C14 C13 -177.5(5) . . . . ?
C12 C13 C14 C9 1.2(9) . . . . ?
N2 C13 C14 C9 -177.7(6) . . . . ?
O1 C1 Er1 O6 -141.8(3) . . . 4 ?
O2 C1 Er1 O6 35.7(3) . . . 4 ?
C2 C1 Er1 O6 129(7) . . . 4 ?
O1 C1 Er1 O2 73.2(7) . . . 4 ?
O2 C1 Er1 O2 -109.3(5) . . . 4 ?
C2 C1 Er1 O2 -16(7) . . . 4 ?
O1 C1 Er1 O4 -8.6(4) . . . 4 ?
O2 C1 Er1 O4 168.9(3) . . . 4 ?
C2 C1 Er1 O4 -98(7) . . . 4 ?
O1 C1 Er1 O7 139.5(3) . . . . ?
O2 C1 Er1 O7 -43.0(3) . . . . ?
C2 C1 Er1 O7 50(7) . . . . ?
O1 C1 Er1 O5 69.1(3) . . . . ?
O2 C1 Er1 O5 -113.4(3) . . . . ?
C2 C1 Er1 O5 -21(7) . . . . ?
O1 C1 Er1 O3 -81.1(4) . . . . ?
O2 C1 Er1 O3 96.4(3) . . . . ?
C2 C1 Er1 O3 -171(7) . . . . ?
O2 C1 Er1 O1 177.5(5) . . . . ?
C2 C1 Er1 O1 -90(7) . . . . ?
O1 C1 Er1 O2 -177.5(5) . . . . ?
C2 C1 Er1 O2 93(7) . . . . ?
C3 C4 N1 N1 178.0(7) . . . 5 ?
C5 C4 N1 N1 -1.1(11) . . . 5 ?
C14 C13 N2 N2 -9.4(10) . . . 7_566 ?
C12 C13 N2 N2 171.7(7) . . . 7_566 ?
O2 C1 O1 Er1 -2.4(5) . . . . ?
C2 C1 O1 Er1 176.3(5) . . . . ?
O6 Er1 O1 C1 52.1(4) 4 . . . ?
O2 Er1 O1 C1 -156.1(3) 4 . . . ?
O4 Er1 O1 C1 171.2(4) 4 . . . ?
O7 Er1 O1 C1 -45.0(4) . . . . ?
O5 Er1 O1 C1 -106.6(4) . . . . ?
O3 Er1 O1 C1 90.9(4) . . . . ?
O2 Er1 O1 C1 1.4(3) . . . . ?
O1 C1 O2 Er1 -161.3(4) . . . 4_545 ?
C2 C1 O2 Er1 19.9(8) . . . 4_545 ?
Er1 C1 O2 Er1 -163.8(5) . . . 4_545 ?
O1 C1 O2 Er1 2.4(5) . . . . ?
C2 C1 O2 Er1 -176.4(4) . . . . ?
O6 Er1 O2 C1 -148.5(3) 4 . . . ?
O2 Er1 O2 C1 150.6(3) 4 . . . ?
O4 Er1 O2 C1 -13.7(4) 4 . . . ?
O7 Er1 O2 C1 135.0(3) . . . . ?
O5 Er1 O2 C1 66.7(3) . . . . ?
O3 Er1 O2 C1 -77.2(3) . . . . ?
O1 Er1 O2 C1 -1.4(3) . . . . ?
O6 Er1 O2 Er1 16.0(2) 4 . . 4_545 ?
O2 Er1 O2 Er1 -45.0(2) 4 . . 4_545 ?
O4 Er1 O2 Er1 150.81(19) 4 . . 4_545 ?
O7 Er1 O2 Er1 -60.6(2) . . . 4_545 ?
O5 Er1 O2 Er1 -128.8(2) . . . 4_545 ?
O3 Er1 O2 Er1 87.3(2) . . . 4_545 ?
O1 Er1 O2 Er1 163.1(3) . . . 4_545 ?
C1 Er1 O2 Er1 164.5(4) . . . 4_545 ?
O7 C8 O4 Er1 -9.3(11) . . . 4_545 ?
C9 C8 O4 Er1 172.8(4) . . . 4_545 ?
C2 C7 O6 Er1 -30.5(8) . . . 4_545 ?
C6 C7 O6 Er1 149.3(5) . . . 4_545 ?
O4 C8 O7 Er1 -42.8(9) . . . . ?
C9 C8 O7 Er1 135.1(4) . . . . ?
O6 Er1 O7 C8 -34.8(5) 4 . . . ?
O2 Er1 O7 C8 -110.8(5) 4 . . . ?
O4 Er1 O7 C8 -164.5(5) 4 . . . ?
O5 Er1 O7 C8 164.5(5) . . . . ?
O3 Er1 O7 C8 10.2(6) . . . . ?
O1 Er1 O7 C8 99.9(5) . . . . ?
O2 Er1 O7 C8 62.3(5) . . . . ?
C1 Er1 O7 C8 81.4(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.818
_refine_diff_density_min         -2.087
_refine_diff_density_rms         0.145
####################################################################### 
# 
# 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_p2015110911_0m
_audit_block_doi                 10.5517/ccdc.csd.cc1nlljc
_database_code_depnum_ccdc_archive 'CCDC 1537213'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C7CC01898C 2017
_audit_update_record             
;
2017-03-10 deposited with the CCDC.
2017-06-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H6 N2 Nd O7.50'
_chemical_formula_weight         466.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'
Nd Nd -0.1943 3.0179 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P1

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

_cell_length_a                   15.528(4)
_cell_length_b                   15.999(4)
_cell_length_c                   13.519(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.643(16)
_cell_angle_gamma                90.00
_cell_volume                     3099.7(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5585
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      27.06

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.000
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             896
_exptl_absorpt_coefficient_mu    1.697
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.8487
_exptl_absorpt_correction_T_max  0.9352
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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            17973
_diffrn_reflns_av_R_equivalents  0.0621
_diffrn_reflns_av_sigmaI/netI    0.0720
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.07
_diffrn_reflns_theta_max         25.00
_reflns_number_total             5433
_reflns_number_gt                4189
_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)+(0.1500P)²+100.0000P] 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         5433
_refine_ls_number_parameters     210
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1390
_refine_ls_R_factor_gt           0.1276
_refine_ls_wR_factor_ref         0.3178
_refine_ls_wR_factor_gt          0.3124
_refine_ls_goodness_of_fit_ref   1.158
_refine_ls_restrained_S_all      1.159
_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
C1 C 0.3575(11) 0.9912(10) 0.8094(13) 0.030(4) Uani 1 1 d . . .
C2 C 0.2597(5) 0.9817(8) 0.7344(6) 0.120(14) Uani 1 1 d G . .
C3 C 0.2288(5) 0.9744(8) 0.6236(6) 0.029(4) Uani 1 1 d G . .
C4 C 0.1354(6) 0.9575(8) 0.5630(5) 0.028(4) Uani 1 1 d G . .
H4 H 0.1148 0.9527 0.4889 0.033 Uiso 1 1 calc R . .
C5 C 0.0729(5) 0.9479(9) 0.6131(8) 0.053(5) Uani 1 1 d G . .
H5 H 0.0104 0.9366 0.5726 0.063 Uiso 1 1 calc R . .
C6 C 0.1038(6) 0.9552(9) 0.7239(8) 0.035(4) Uani 1 1 d G . .
C7 C 0.1971(7) 0.9721(8) 0.7845(5) 0.050(5) Uani 1 1 d G . .
H7 H 0.2178 0.9770 0.8586 0.060 Uiso 1 1 calc R . .
C8 C 0.4660(12) 0.8336(11) 0.5434(17) 0.043(5) Uani 1 1 d . . .
C9 C 0.4491(16) 0.7447(11) 0.5606(17) 0.048(5) Uani 1 1 d . . .
C10 C 0.4824(17) 0.6800(12) 0.5158(17) 0.054(6) Uani 1 1 d . . .
H10 H 0.5170 0.6915 0.4744 0.065 Uiso 1 1 calc R . .
C11 C 0.463(2) 0.5976(13) 0.534(2) 0.082(9) Uani 1 1 d . . .
C12 C 0.416(2) 0.5803(15) 0.602(3) 0.091(10) Uani 1 1 d . . .
H12 H 0.4029 0.5250 0.6135 0.110 Uiso 1 1 calc R . .
C13 C 0.4031(19) 0.7287(14) 0.634(2) 0.065(6) Uani 1 1 d . . .
C25 C 0.387(3) 0.6441(13) 0.654(3) 0.117(15) Uani 1 1 d . . .
H25 H 0.3579 0.6311 0.7004 0.141 Uiso 1 1 calc R . .
N1 N 0.0428(12) 0.9534(11) 0.7821(13) 0.052(5) Uani 1 1 d . . .
N2 N 0.504(2) 0.5367(10) 0.487(2) 0.079(7) Uani 1 1 d . . .
Nd1 Nd 0.42680(5) 1.04172(5) 0.59229(6) 0.0183(3) Uani 1 1 d . . .
O1 O 0.3891(8) 0.9896(8) 0.9076(7) 0.034(3) Uani 1 1 d U . .
O2 O 0.4141(8) 1.0105(9) 0.7643(8) 0.038(3) Uani 1 1 d . . .
O3 O 0.2839(8) 0.9905(11) 0.5707(9) 0.050(4) Uani 1 1 d . . .
O4 O 0.3166(12) 1.1619(11) 0.5358(19) 0.100(7) Uani 1 1 d . . .
O5 O 0.5000 1.1532(10) 0.7500 0.059(6) Uani 1 2 d S . .
O6 O 0.4435(8) 0.8876(7) 0.5922(9) 0.035(3) Uani 1 1 d . . .
O7 O 0.5004(10) 0.8466(7) 0.4721(10) 0.043(3) Uani 1 1 d . . .
O8 O 0.3725(16) 0.7849(10) 0.6799(17) 0.090(7) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.226(19) . ?
C1 O2 1.285(18) . ?
C1 C2 1.474(18) . ?
C2 C3 1.3900 . ?
C2 C7 1.3900 . ?
C3 O3 1.335(12) . ?
C3 C4 1.3900 . ?
C4 C5 1.3900 . ?
C4 H4 0.9300 . ?
C5 C6 1.3900 . ?
C5 H5 0.9300 . ?
C6 C7 1.3900 . ?
C6 N1 1.446(18) . ?
C7 H7 0.9300 . ?
C8 O6 1.22(2) . ?
C8 O7 1.29(2) . ?
C8 C9 1.48(2) . ?
C9 C10 1.40(3) . ?
C9 C13 1.46(3) . ?
C10 C11 1.40(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.41(3) . ?
C11 N2 1.44(3) . ?
C12 C25 1.40(3) . ?
C12 H12 0.9300 . ?
C13 O8 1.28(3) . ?
C13 C25 1.42(3) . ?
C25 H25 0.9300 . ?
N1 N1 1.28(3) 2_556 ?
N2 N2 1.25(3) 3_666 ?
Nd1 O3 2.276(11) . ?
Nd1 O1 2.388(9) 4_575 ?
Nd1 O7 2.446(12) 3_676 ?
Nd1 O2 2.460(9) . ?
Nd1 O6 2.479(11) . ?
Nd1 O4 2.491(15) . ?
Nd1 O2 2.534(12) 2_656 ?
Nd1 O5 2.674(11) . ?
Nd1 Nd1 3.9858(17) 2_656 ?
O1 Nd1 2.388(9) 4_576 ?
O2 Nd1 2.534(12) 2_656 ?
O5 Nd1 2.674(11) 2_656 ?
O7 Nd1 2.446(12) 3_676 ?

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 C1 O2 117.2(16) . . ?
O1 C1 C2 128.3(13) . . ?
O2 C1 C2 114.2(13) . . ?
C3 C2 C7 120.0 . . ?
C3 C2 C1 125.9(8) . . ?
C7 C2 C1 113.8(8) . . ?
O3 C3 C4 117.4(8) . . ?
O3 C3 C2 122.3(8) . . ?
C4 C3 C2 120.0 . . ?
C5 C4 C3 120.0 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 120.0 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C7 C6 C5 120.0 . . ?
C7 C6 N1 115.8(9) . . ?
C5 C6 N1 124.0(9) . . ?
C6 C7 C2 120.0 . . ?
C6 C7 H7 120.0 . . ?
C2 C7 H7 120.0 . . ?
O6 C8 O7 125.3(15) . . ?
O6 C8 C9 119.5(17) . . ?
O7 C8 C9 115.0(17) . . ?
C10 C9 C13 122.0(18) . . ?
C10 C9 C8 121.8(17) . . ?
C13 C9 C8 116.0(17) . . ?
C11 C10 C9 118.7(18) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
C10 C11 C12 120(2) . . ?
C10 C11 N2 113.1(19) . . ?
C12 C11 N2 126.2(19) . . ?
C25 C12 C11 122(2) . . ?
C25 C12 H12 119.2 . . ?
C11 C12 H12 119.2 . . ?
O8 C13 C25 117(2) . . ?
O8 C13 C9 125.2(18) . . ?
C25 C13 C9 117(2) . . ?
C12 C25 C13 120(2) . . ?
C12 C25 H25 120.2 . . ?
C13 C25 H25 120.2 . . ?
N1 N1 C6 110.9(18) 2_556 . ?
N2 N2 C11 113(2) 3_666 . ?
O3 Nd1 O1 87.4(4) . 4_575 ?
O3 Nd1 O7 141.1(5) . 3_676 ?
O1 Nd1 O7 75.1(4) 4_575 3_676 ?
O3 Nd1 O2 67.6(4) . . ?
O1 Nd1 O2 150.4(4) 4_575 . ?
O7 Nd1 O2 134.5(4) 3_676 . ?
O3 Nd1 O6 74.9(5) . . ?
O1 Nd1 O6 76.9(4) 4_575 . ?
O7 Nd1 O6 131.5(4) 3_676 . ?
O2 Nd1 O6 81.1(4) . . ?
O3 Nd1 O4 73.6(6) . . ?
O1 Nd1 O4 88.8(6) 4_575 . ?
O7 Nd1 O4 71.6(6) 3_676 . ?
O2 Nd1 O4 98.7(6) . . ?
O6 Nd1 O4 145.8(5) . . ?
O3 Nd1 O2 129.9(4) . 2_656 ?
O1 Nd1 O2 122.2(3) 4_575 2_656 ?
O7 Nd1 O2 88.2(4) 3_676 2_656 ?
O2 Nd1 O2 69.3(4) . 2_656 ?
O6 Nd1 O2 74.5(4) . 2_656 ?
O4 Nd1 O2 137.7(6) . 2_656 ?
O3 Nd1 O5 115.9(4) . . ?
O1 Nd1 O5 146.3(4) 4_575 . ?
O7 Nd1 O5 71.6(3) 3_676 . ?
O2 Nd1 O5 63.0(4) . . ?
O6 Nd1 O5 130.6(4) . . ?
O4 Nd1 O5 76.2(6) . . ?
O2 Nd1 O5 62.1(3) 2_656 . ?
O3 Nd1 Nd1 105.3(3) . 2_656 ?
O1 Nd1 Nd1 158.1(3) 4_575 2_656 ?
O7 Nd1 Nd1 103.3(3) 3_676 2_656 ?
O2 Nd1 Nd1 37.7(3) . 2_656 ?
O6 Nd1 Nd1 89.1(3) . 2_656 ?
O4 Nd1 Nd1 111.7(5) . 2_656 ?
O2 Nd1 Nd1 36.41(19) 2_656 2_656 ?
O5 Nd1 Nd1 41.8(3) . 2_656 ?
C1 O1 Nd1 166.3(12) . 4_576 ?
C1 O2 Nd1 144.6(11) . . ?
C1 O2 Nd1 109.2(10) . 2_656 ?
Nd1 O2 Nd1 105.9(4) . 2_656 ?
C3 O3 Nd1 142.6(9) . . ?
Nd1 O5 Nd1 96.4(5) . 2_656 ?
C8 O6 Nd1 139.4(11) . . ?
C8 O7 Nd1 140.1(11) . 3_676 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -172.2(13) . . . . ?
O2 C1 C2 C3 14(2) . . . . ?
O1 C1 C2 C7 2(2) . . . . ?
O2 C1 C2 C7 -171.8(11) . . . . ?
C7 C2 C3 O3 173.8(14) . . . . ?
C1 C2 C3 O3 -12.6(16) . . . . ?
C7 C2 C3 C4 0.0 . . . . ?
C1 C2 C3 C4 173.7(14) . . . . ?
O3 C3 C4 C5 -174.1(13) . . . . ?
C2 C3 C4 C5 0.0 . . . . ?
C3 C4 C5 C6 0.0 . . . . ?
C4 C5 C6 C7 0.0 . . . . ?
C4 C5 C6 N1 174.4(14) . . . . ?
C5 C6 C7 C2 0.0 . . . . ?
N1 C6 C7 C2 -174.9(13) . . . . ?
C3 C2 C7 C6 0.0 . . . . ?
C1 C2 C7 C6 -174.4(13) . . . . ?
O6 C8 C9 C10 -173(2) . . . . ?
O7 C8 C9 C10 10(3) . . . . ?
O6 C8 C9 C13 2(3) . . . . ?
O7 C8 C9 C13 -175(2) . . . . ?
C13 C9 C10 C11 6(4) . . . . ?
C8 C9 C10 C11 -179(3) . . . . ?
C9 C10 C11 C12 -4(5) . . . . ?
C9 C10 C11 N2 -178(3) . . . . ?
C10 C11 C12 C25 0(6) . . . . ?
N2 C11 C12 C25 173(4) . . . . ?
C10 C9 C13 O8 179(3) . . . . ?
C8 C9 C13 O8 4(4) . . . . ?
C10 C9 C13 C25 -4(4) . . . . ?
C8 C9 C13 C25 -179(3) . . . . ?
C11 C12 C25 C13 2(6) . . . . ?
O8 C13 C25 C12 177(3) . . . . ?
C9 C13 C25 C12 0(5) . . . . ?
C7 C6 N1 N1 167.7(6) . . . 2_556 ?
C5 C6 N1 N1 -7.0(12) . . . 2_556 ?
C10 C11 N2 N2 173(4) . . . 3_666 ?
C12 C11 N2 N2 0(6) . . . 3_666 ?
O2 C1 O1 Nd1 -141(4) . . . 4_576 ?
C2 C1 O1 Nd1 45(5) . . . 4_576 ?
O1 C1 O2 Nd1 -173.3(13) . . . . ?
C2 C1 O2 Nd1 1(3) . . . . ?
O1 C1 O2 Nd1 -1.5(18) . . . 2_656 ?
C2 C1 O2 Nd1 172.9(10) . . . 2_656 ?
O3 Nd1 O2 C1 -10.7(19) . . . . ?
O1 Nd1 O2 C1 -45(2) 4_575 . . . ?
O7 Nd1 O2 C1 130.2(19) 3_676 . . . ?
O6 Nd1 O2 C1 -88(2) . . . . ?
O4 Nd1 O2 C1 57(2) . . . . ?
O2 Nd1 O2 C1 -164.6(18) 2_656 . . . ?
O5 Nd1 O2 C1 127(2) . . . . ?
Nd1 Nd1 O2 C1 172(2) 2_656 . . . ?
O3 Nd1 O2 Nd1 177.4(7) . . . 2_656 ?
O1 Nd1 O2 Nd1 142.6(7) 4_575 . . 2_656 ?
O7 Nd1 O2 Nd1 -41.7(8) 3_676 . . 2_656 ?
O6 Nd1 O2 Nd1 100.2(5) . . . 2_656 ?
O4 Nd1 O2 Nd1 -114.4(6) . . . 2_656 ?
O2 Nd1 O2 Nd1 23.5(6) 2_656 . . 2_656 ?
O5 Nd1 O2 Nd1 -44.9(4) . . . 2_656 ?
C4 C3 O3 Nd1 166.6(14) . . . . ?
C2 C3 O3 Nd1 -7(2) . . . . ?
O1 Nd1 O3 C3 177(2) 4_575 . . . ?
O7 Nd1 O3 C3 -120.3(17) 3_676 . . . ?
O2 Nd1 O3 C3 13.9(18) . . . . ?
O6 Nd1 O3 C3 100(2) . . . . ?
O4 Nd1 O3 C3 -93(2) . . . . ?
O2 Nd1 O3 C3 46(2) 2_656 . . . ?
O5 Nd1 O3 C3 -28(2) . . . . ?
Nd1 Nd1 O3 C3 16(2) 2_656 . . . ?
O3 Nd1 O5 Nd1 84.1(4) . . . 2_656 ?
O1 Nd1 O5 Nd1 -146.3(6) 4_575 . . 2_656 ?
O7 Nd1 O5 Nd1 -137.3(3) 3_676 . . 2_656 ?
O2 Nd1 O5 Nd1 40.3(3) . . . 2_656 ?
O6 Nd1 O5 Nd1 -7.9(4) . . . 2_656 ?
O4 Nd1 O5 Nd1 147.8(5) . . . 2_656 ?
O2 Nd1 O5 Nd1 -39.3(3) 2_656 . . 2_656 ?
O7 C8 O6 Nd1 7(3) . . . . ?
C9 C8 O6 Nd1 -169.0(14) . . . . ?
O3 Nd1 O6 C8 122.9(18) . . . . ?
O1 Nd1 O6 C8 32.0(17) 4_575 . . . ?
O7 Nd1 O6 C8 -24.0(19) 3_676 . . . ?
O2 Nd1 O6 C8 -168.0(18) . . . . ?
O4 Nd1 O6 C8 100(2) . . . . ?
O2 Nd1 O6 C8 -97.2(18) 2_656 . . . ?
O5 Nd1 O6 C8 -125.8(17) . . . . ?
Nd1 Nd1 O6 C8 -131.0(17) 2_656 . . . ?
O6 C8 O7 Nd1 16(3) . . . 3_676 ?
C9 C8 O7 Nd1 -167.2(14) . . . 3_676 ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         10.118
_refine_diff_density_min         -5.048
_refine_diff_density_rms         0.391
####################################################################### 
# 
# 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_p2015110908qianse_0m
_audit_block_doi                 10.5517/ccdc.csd.cc1nllb5
_database_code_depnum_ccdc_archive 'CCDC 1537207'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C7CC01898C 2017
_audit_update_record             
;
2017-03-10 deposited with the CCDC.
2017-06-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H24 Ce2 N6 O18'
_chemical_formula_weight         1072.82

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'
Ce Ce -0.2486 2.6331 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   20.0164(6)
_cell_length_b                   7.3972(2)
_cell_length_c                   25.7120(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.0930(10)
_cell_angle_gamma                90.00
_cell_volume                     3675.73(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8344
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      27.69

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.939
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2096
_exptl_absorpt_coefficient_mu    2.535
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.7856
_exptl_absorpt_correction_T_max  0.8229
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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            11517
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_sigmaI/netI    0.0201
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.11
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3237
_reflns_number_gt                2988
_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)+(0.0378P)²+40.6967P] 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         3237
_refine_ls_number_parameters     267
_refine_ls_number_restraints     38
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0300
_refine_ls_wR_factor_ref         0.0785
_refine_ls_wR_factor_gt          0.0765
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_restrained_S_all      2.261
_refine_ls_shift/su_max          0.587
_refine_ls_shift/su_mean         0.015

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
C1 C 0.07403(5) -0.02396(13) 0.09608(4) 0.0255(3) Uani 1 1 d . . .
H1 H 0.0565 -0.1403 0.0889 0.031 Uiso 1 1 calc R . .
C2 C 0.20945(7) -0.04017(15) 0.47847(4) 0.0384(4) Uani 1 1 d . . .
C3 C 0.14977(5) 0.18815(13) 0.15679(4) 0.0237(3) Uani 1 1 d . . .
C4 C 0.14117(5) -0.14368(13) 0.18221(4) 0.0221(3) Uani 1 1 d . . .
C5 C 0.12149(5) 0.01063(13) 0.14491(4) 0.0229(3) Uani 1 1 d . . .
C6 C 0.22269(6) -0.00260(15) 0.42914(4) 0.0350(3) Uani 1 1 d . . .
H6 H 0.2457 -0.0872 0.4134 0.042 Uiso 1 1 calc R . .
C7 C 0.20175(6) 0.16103(14) 0.40315(4) 0.0310(3) Uani 1 1 d . . .
C8 C 0.05209(6) 0.10931(14) 0.05786(4) 0.0295(3) Uani 1 1 d . . .
C9 C 0.12489(6) 0.32140(14) 0.11765(4) 0.0335(3) Uani 1 1 d . . .
H9 H 0.1410 0.4392 0.1244 0.040 Uiso 1 1 calc R . .
C10 C 0.07774(6) 0.28415(14) 0.06990(4) 0.0364(3) Uani 1 1 d . . .
H10 H 0.0626 0.3765 0.0451 0.044 Uiso 1 1 calc R . .
C11 C 0.15246(7) 0.24621(19) 0.47640(5) 0.0486(4) Uani 1 1 d . . .
H11 H 0.1281 0.3278 0.4920 0.058 Uiso 1 1 calc R . .
C12 C 0.21631(6) 0.20075(14) 0.35033(4) 0.0289(3) Uani 1 1 d . . .
C13 C 0.16724(6) 0.28742(16) 0.42801(4) 0.0389(3) Uani 1 1 d . . .
C14 C 0.17404(7) 0.08417(19) 0.50123(5) 0.0489(4) Uani 1 1 d . . .
H14 H 0.1646 0.0577 0.5340 0.059 Uiso 1 1 calc R . .
C16 C 0.05495(12) 0.2938(2) 0.23270(8) 0.2623(15) Uani 1 1 d DU . .
H16 H 0.0491 0.2673 0.1964 0.315 Uiso 1 1 calc R . .
C17 C 0.0000 -0.0889(2) 0.2500 0.7137(18) Uani 1 2 d SDU . .
Ce1 Ce 0.202608(3) 0.537161(7) 0.248942(2) 0.01950(1) Uani 1 1 d . . .
H1M H 0.1604 0.4661 0.3770 0.023 Uiso 1 1 d RD . .
H1W H 0.1737 0.8338 0.3301 0.023 Uiso 1 1 d RD . .
H2W H 0.1210 0.7367 0.3240 0.023 Uiso 1 1 d RD . .
H3W H 0.0487 0.4882 0.3596 0.023 Uiso 1 1 d RD . .
H4W H 0.0277 0.7059 0.3789 0.023 Uiso 1 1 d RD . .
N1 N 0.23072(6) -0.20081(13) 0.50886(4) 0.0434(3) Uani 1 1 d . . .
N2 N 0.00692(5) 0.08100(12) 0.00571(3) 0.0329(3) Uani 1 1 d . . .
N3 N 0.02531(15) 0.1246(3) 0.26786(8) 0.31573(18) Uani 1 1 d DU . .
O1 O 0.03118(6) 0.63473(16) 0.34097(4) 0.0816(4) Uani 1 1 d D . .
O2 O 0.19700(4) 0.23033(9) 0.20192(3) 0.0278(2) Uani 1 1 d . . .
O3 O 0.19110(4) -0.13058(9) 0.22445(3) 0.0269(2) Uani 1 1 d . . .
O4 O 0.10987(4) -0.29187(10) 0.17297(3) 0.0363(2) Uani 1 1 d . . .
O5 O 0.16038(5) 0.73028(11) 0.31751(3) 0.0561(3) Uani 1 1 d D . .
O6 O 0.20535(5) 0.36010(10) 0.33246(3) 0.0432(2) Uani 1 1 d . . .
O7 O 0.23798(4) 0.07631(10) 0.32581(3) 0.0309(2) Uani 1 1 d . . .
O8 O 0.14794(5) 0.45176(11) 0.40600(3) 0.0516(3) Uani 1 1 d D . .
O9 O 0.08168(6) 0.43906(19) 0.24582(5) 0.1259(5) Uani 1 1 d D . .
C18 C 0.0228(2) 0.1293(4) 0.33334(6) 0.4187(17) Uani 1 1 d DU . .


_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
C1 C8 1.3805(14) . ?
C1 C5 1.3867(12) . ?
C2 C14 1.3811(19) . ?
C2 C6 1.3896(17) . ?
C2 N1 1.4249(15) . ?
C3 O2 1.3290(10) . ?
C3 C9 1.4040(13) . ?
C3 C5 1.4311(13) . ?
C4 O4 1.2542(12) . ?
C4 O3 1.2738(10) . ?
C4 C5 1.4768(13) . ?
C4 Ce1 2.9885(9) 1_545 ?
C6 C7 1.3933(15) . ?
C7 C13 1.4104(17) . ?
C7 C12 1.4906(15) . ?
C8 C10 1.3961(15) . ?
C8 N2 1.4241(12) . ?
C9 C10 1.3679(14) . ?
C11 C14 1.3738(19) . ?
C11 C13 1.3858(18) . ?
C12 O7 1.2551(13) . ?
C12 O6 1.2634(13) . ?
C13 O8 1.3541(14) . ?
C16 O9 1.208(2) . ?
C16 N3 1.736(3) . ?
C17 N3 1.686(2) . ?
C17 N3 1.686(2) 2 ?
Ce1 O3 2.4033(7) 4 ?
Ce1 O6 2.5037(8) . ?
Ce1 O9 2.5082(12) . ?
Ce1 O2 2.5207(7) 4 ?
Ce1 O7 2.5265(8) 4 ?
Ce1 O3 2.5327(7) 1_565 ?
Ce1 O2 2.5602(7) . ?
Ce1 O5 2.5767(9) . ?
Ce1 O4 2.6406(7) 1_565 ?
Ce1 C4 2.9885(9) 1_565 ?
Ce1 Ce1 4.15071(10) 4 ?
Ce1 Ce1 4.15071(11) 4_545 ?
N1 N1 1.231(2) 7_546 ?
N2 N2 1.2476(18) 5 ?
N3 N3 1.177(5) 2 ?
N3 C18 1.698(3) . ?
O2 Ce1 2.5207(7) 4_545 ?
O3 Ce1 2.4033(7) 4_545 ?
O3 Ce1 2.5327(7) 1_545 ?
O4 Ce1 2.6406(7) 1_545 ?
O7 Ce1 2.5265(8) 4_545 ?

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
C8 C1 C5 121.92(9) . . ?
C14 C2 C6 119.64(11) . . ?
C14 C2 N1 115.85(11) . . ?
C6 C2 N1 124.51(11) . . ?
O2 C3 C9 119.99(9) . . ?
O2 C3 C5 123.62(8) . . ?
C9 C3 C5 116.39(8) . . ?
O4 C4 O3 118.05(8) . . ?
O4 C4 C5 121.12(8) . . ?
O3 C4 C5 120.82(8) . . ?
O4 C4 Ce1 61.89(5) . 1_545 ?
O3 C4 Ce1 57.07(5) . 1_545 ?
C5 C4 Ce1 169.65(7) . 1_545 ?
C1 C5 C3 120.14(8) . . ?
C1 C5 C4 116.70(8) . . ?
C3 C5 C4 123.15(8) . . ?
C2 C6 C7 120.43(11) . . ?
C6 C7 C13 118.70(10) . . ?
C6 C7 C12 120.16(10) . . ?
C13 C7 C12 121.14(9) . . ?
C1 C8 C10 118.25(8) . . ?
C1 C8 N2 124.86(9) . . ?
C10 C8 N2 116.84(9) . . ?
C10 C9 C3 122.35(10) . . ?
C9 C10 C8 120.89(9) . . ?
C14 C11 C13 119.63(13) . . ?
O7 C12 O6 123.48(10) . . ?
O7 C12 C7 119.22(9) . . ?
O6 C12 C7 117.30(10) . . ?
O8 C13 C11 117.92(12) . . ?
O8 C13 C7 121.73(11) . . ?
C11 C13 C7 120.35(11) . . ?
C11 C14 C2 121.20(12) . . ?
O9 C16 N3 132.99(17) . . ?
N3 C17 N3 40.87(16) . 2 ?
O3 Ce1 O6 70.47(3) 4 . ?
O3 Ce1 O9 129.43(4) 4 . ?
O6 Ce1 O9 71.43(3) . . ?
O3 Ce1 O2 67.60(2) 4 4 ?
O6 Ce1 O2 91.73(2) . 4 ?
O9 Ce1 O2 144.77(4) . 4 ?
O3 Ce1 O7 73.65(2) 4 4 ?
O6 Ce1 O7 143.41(3) . 4 ?
O9 Ce1 O7 130.57(3) . 4 ?
O2 Ce1 O7 81.06(2) 4 4 ?
O3 Ce1 O3 126.030(16) 4 1_565 ?
O6 Ce1 O3 134.52(2) . 1_565 ?
O9 Ce1 O3 104.37(4) . 1_565 ?
O2 Ce1 O3 65.39(2) 4 1_565 ?
O7 Ce1 O3 74.33(2) 4 1_565 ?
O3 Ce1 O2 66.64(2) 4 . ?
O6 Ce1 O2 85.97(2) . . ?
O9 Ce1 O2 78.76(4) . . ?
O2 Ce1 O2 132.099(13) 4 . ?
O7 Ce1 O2 73.37(2) 4 . ?
O3 Ce1 O2 138.84(2) 1_565 . ?
O3 Ce1 O5 121.02(2) 4 . ?
O6 Ce1 O5 68.96(3) . . ?
O9 Ce1 O5 72.33(4) . . ?
O2 Ce1 O5 72.76(3) 4 . ?
O7 Ce1 O5 139.49(3) 4 . ?
O3 Ce1 O5 66.88(3) 1_565 . ?
O2 Ce1 O5 146.38(3) . . ?
O3 Ce1 O4 149.04(3) 4 1_565 ?
O6 Ce1 O4 137.67(3) . 1_565 ?
O9 Ce1 O4 68.17(3) . 1_565 ?
O2 Ce1 O4 114.48(2) 4 1_565 ?
O7 Ce1 O4 76.22(2) 4 1_565 ?
O3 Ce1 O4 49.49(2) 1_565 1_565 ?
O2 Ce1 O4 98.01(2) . 1_565 ?
O5 Ce1 O4 87.02(2) . 1_565 ?
O3 Ce1 C4 140.60(3) 4 1_565 ?
O6 Ce1 C4 145.04(3) . 1_565 ?
O9 Ce1 C4 87.75(4) . 1_565 ?
O2 Ce1 C4 89.72(2) 4 1_565 ?
O7 Ce1 C4 71.18(3) 4 1_565 ?
O3 Ce1 C4 24.97(2) 1_565 1_565 ?
O2 Ce1 C4 117.93(2) . 1_565 ?
O5 Ce1 C4 78.21(3) . 1_565 ?
O4 Ce1 C4 24.77(2) 1_565 1_565 ?
O3 Ce1 Ce1 95.082(17) 4 4 ?
O6 Ce1 Ce1 123.164(17) . 4 ?
O9 Ce1 Ce1 133.81(3) . 4 ?
O2 Ce1 Ce1 35.539(14) 4 4 ?
O7 Ce1 Ce1 66.656(16) 4 4 ?
O3 Ce1 Ce1 31.811(15) 1_565 4 ?
O2 Ce1 Ce1 139.449(18) . 4 ?
O5 Ce1 Ce1 74.17(2) . 4 ?
O4 Ce1 Ce1 79.268(16) 1_565 4 ?
C4 Ce1 Ce1 54.685(17) 1_565 4 ?
O3 Ce1 Ce1 33.745(16) 4 4_545 ?
O6 Ce1 Ce1 67.341(19) . 4_545 ?
O9 Ce1 Ce1 100.17(3) . 4_545 ?
O2 Ce1 Ce1 101.335(16) 4 4_545 ?
O7 Ce1 Ce1 78.930(16) 4 4_545 ?
O3 Ce1 Ce1 151.598(18) 1_565 4_545 ?
O2 Ce1 Ce1 34.909(14) . 4_545 ?
O5 Ce1 Ce1 135.668(18) . 4_545 ?
O4 Ce1 Ce1 131.862(16) 1_565 4_545 ?
C4 Ce1 Ce1 146.078(19) 1_565 4_545 ?
Ce1 Ce1 Ce1 126.018(3) 4 4_545 ?
N1 N1 C2 114.61(13) 7_546 . ?
N2 N2 C8 114.24(10) 5 . ?
N3 N3 C17 69.56(8) 2 . ?
N3 N3 C18 122.2(4) 2 . ?
C17 N3 C18 101.83(16) . . ?
N3 N3 C16 86.27(18) 2 . ?
C17 N3 C16 130.75(14) . . ?
C18 N3 C16 127.15(17) . . ?
C3 O2 Ce1 126.69(6) . 4_545 ?
C3 O2 Ce1 123.66(6) . . ?
Ce1 O2 Ce1 109.55(2) 4_545 . ?
C4 O3 Ce1 136.20(6) . 4_545 ?
C4 O3 Ce1 97.96(6) . 1_545 ?
Ce1 O3 Ce1 114.44(2) 4_545 1_545 ?
C4 O4 Ce1 93.34(5) . 1_545 ?
C12 O6 Ce1 139.72(7) . . ?
C12 O7 Ce1 139.37(7) . 4_545 ?
C16 O9 Ce1 128.29(14) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 C1 C5 C3 -0.57(17) . . . . ?
C8 C1 C5 C4 -179.56(10) . . . . ?
O2 C3 C5 C1 -177.85(10) . . . . ?
C9 C3 C5 C1 2.23(16) . . . . ?
O2 C3 C5 C4 1.07(17) . . . . ?
C9 C3 C5 C4 -178.84(10) . . . . ?
O4 C4 C5 C1 -8.86(16) . . . . ?
O3 C4 C5 C1 170.29(10) . . . . ?
Ce1 C4 C5 C1 95.2(3) 1_545 . . . ?
O4 C4 C5 C3 172.18(10) . . . . ?
O3 C4 C5 C3 -8.67(16) . . . . ?
Ce1 C4 C5 C3 -83.8(4) 1_545 . . . ?
C14 C2 C6 C7 1.35(17) . . . . ?
N1 C2 C6 C7 -177.92(10) . . . . ?
C2 C6 C7 C13 0.26(16) . . . . ?
C2 C6 C7 C12 179.80(10) . . . . ?
C5 C1 C8 C10 -1.50(18) . . . . ?
C5 C1 C8 N2 175.91(11) . . . . ?
O2 C3 C9 C10 178.17(11) . . . . ?
C5 C3 C9 C10 -1.91(18) . . . . ?
C3 C9 C10 C8 -0.1(2) . . . . ?
C1 C8 C10 C9 1.86(19) . . . . ?
N2 C8 C10 C9 -175.76(11) . . . . ?
C6 C7 C12 O7 10.62(15) . . . . ?
C13 C7 C12 O7 -169.86(10) . . . . ?
C6 C7 C12 O6 -169.95(10) . . . . ?
C13 C7 C12 O6 9.58(15) . . . . ?
C14 C11 C13 O8 -177.01(11) . . . . ?
C14 C11 C13 C7 2.59(18) . . . . ?
C6 C7 C13 O8 177.35(10) . . . . ?
C12 C7 C13 O8 -2.19(16) . . . . ?
C6 C7 C13 C11 -2.24(16) . . . . ?
C12 C7 C13 C11 178.23(10) . . . . ?
C13 C11 C14 C2 -0.95(19) . . . . ?
C6 C2 C14 C11 -1.02(19) . . . . ?
N1 C2 C14 C11 178.31(11) . . . . ?
C14 C2 N1 N1 -171.54(13) . . . 7_546 ?
C6 C2 N1 N1 7.75(19) . . . 7_546 ?
C1 C8 N2 N2 -6.8(2) . . . 5 ?
C10 C8 N2 N2 170.67(13) . . . 5 ?
N3 C17 N3 C18 120.2(4) 2 . . . ?
N3 C17 N3 C16 -65.6(2) 2 . . . ?
O9 C16 N3 N3 132.2(3) . . . 2 ?
O9 C16 N3 C17 -168.9(2) . . . . ?
O9 C16 N3 C18 3.9(4) . . . . ?
C9 C3 O2 Ce1 -141.86(9) . . . 4_545 ?
C5 C3 O2 Ce1 38.23(14) . . . 4_545 ?
C9 C3 O2 Ce1 34.06(14) . . . . ?
C5 C3 O2 Ce1 -145.85(8) . . . . ?
O3 Ce1 O2 C3 -161.06(8) 4 . . . ?
O6 Ce1 O2 C3 128.49(8) . . . . ?
O9 Ce1 O2 C3 56.64(8) . . . . ?
O2 Ce1 O2 C3 -142.82(8) 4 . . . ?
O7 Ce1 O2 C3 -82.06(8) 4 . . . ?
O3 Ce1 O2 C3 -42.41(9) 1_565 . . . ?
O5 Ce1 O2 C3 87.59(8) . . . . ?
O4 Ce1 O2 C3 -9.11(8) 1_565 . . . ?
C4 Ce1 O2 C3 -24.70(9) 1_565 . . . ?
Ce1 Ce1 O2 C3 -91.94(8) 4 . . . ?
Ce1 Ce1 O2 C3 -176.53(9) 4_545 . . . ?
O3 Ce1 O2 Ce1 15.47(3) 4 . . 4_545 ?
O6 Ce1 O2 Ce1 -54.98(3) . . . 4_545 ?
O9 Ce1 O2 Ce1 -126.83(4) . . . 4_545 ?
O2 Ce1 O2 Ce1 33.71(3) 4 . . 4_545 ?
O7 Ce1 O2 Ce1 94.46(3) 4 . . 4_545 ?
O3 Ce1 O2 Ce1 134.12(3) 1_565 . . 4_545 ?
O5 Ce1 O2 Ce1 -95.88(5) . . . 4_545 ?
O4 Ce1 O2 Ce1 167.42(3) 1_565 . . 4_545 ?
C4 Ce1 O2 Ce1 151.83(3) 1_565 . . 4_545 ?
Ce1 Ce1 O2 Ce1 84.59(3) 4 . . 4_545 ?
O4 C4 O3 Ce1 149.67(8) . . . 4_545 ?
C5 C4 O3 Ce1 -29.50(15) . . . 4_545 ?
Ce1 C4 O3 Ce1 138.55(9) 1_545 . . 4_545 ?
O4 C4 O3 Ce1 11.12(10) . . . 1_545 ?
C5 C4 O3 Ce1 -168.06(8) . . . 1_545 ?
O3 C4 O4 Ce1 -10.57(10) . . . 1_545 ?
C5 C4 O4 Ce1 168.60(9) . . . 1_545 ?
O7 C12 O6 Ce1 7.42(18) . . . . ?
C7 C12 O6 Ce1 -171.99(7) . . . . ?
O3 Ce1 O6 C12 -50.55(11) 4 . . . ?
O9 Ce1 O6 C12 95.56(12) . . . . ?
O2 Ce1 O6 C12 -116.01(11) 4 . . . ?
O7 Ce1 O6 C12 -38.74(13) 4 . . . ?
O3 Ce1 O6 C12 -172.32(10) 1_565 . . . ?
O2 Ce1 O6 C12 16.07(11) . . . . ?
O5 Ce1 O6 C12 173.22(12) . . . . ?
O4 Ce1 O6 C12 113.55(11) 1_565 . . . ?
C4 Ce1 O6 C12 152.01(10) 1_565 . . . ?
Ce1 Ce1 O6 C12 -133.68(10) 4 . . . ?
Ce1 Ce1 O6 C12 -14.45(11) 4_545 . . . ?
O6 C12 O7 Ce1 17.94(16) . . . 4_545 ?
C7 C12 O7 Ce1 -162.67(7) . . . 4_545 ?
N3 C16 O9 Ce1 113.3(3) . . . . ?
O3 Ce1 O9 C16 -37.92(16) 4 . . . ?
O6 Ce1 O9 C16 -80.79(15) . . . . ?
O2 Ce1 O9 C16 -145.92(13) 4 . . . ?
O7 Ce1 O9 C16 65.04(16) 4 . . . ?
O3 Ce1 O9 C16 146.56(14) 1_565 . . . ?
O2 Ce1 O9 C16 8.70(14) . . . . ?
O5 Ce1 O9 C16 -153.91(15) . . . . ?
O4 Ce1 O9 C16 112.15(15) 1_565 . . . ?
C4 Ce1 O9 C16 127.75(15) 1_565 . . . ?
Ce1 Ce1 O9 C16 160.69(13) 4 . . . ?
Ce1 Ce1 O9 C16 -19.03(15) 4_545 . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.851
_refine_diff_density_min         -0.912
_refine_diff_density_rms         0.117
####################################################################### 
# 
# 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_p2015110906_0m
_audit_block_doi                 10.5517/ccdc.csd.cc1nll94
_database_code_depnum_ccdc_archive 'CCDC 1537206'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C7CC01898C 2017
_audit_update_record             
;
2017-03-10 deposited with the CCDC.
2017-06-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H24 La2 N6 O18'
_chemical_formula_weight         1070.40

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'
La La -0.2871 2.4523 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   20.108(2)
_cell_length_b                   7.4444(9)
_cell_length_c                   25.868(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.940(4)
_cell_angle_gamma                90.00
_cell_volume                     3741.5(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9944
_cell_measurement_theta_min      4.09
_cell_measurement_theta_max      27.52

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.900
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2088
_exptl_absorpt_coefficient_mu    2.341
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.7996
_exptl_absorpt_correction_T_max  0.8348
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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            13435
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_sigmaI/netI    0.0226
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.63
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3278
_reflns_number_gt                3130
_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)+(0.0339P)²+27.1140P] 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         3278
_refine_ls_number_parameters     267
_refine_ls_number_restraints     38
_refine_ls_R_factor_all          0.0312
_refine_ls_R_factor_gt           0.0299
_refine_ls_wR_factor_ref         0.0775
_refine_ls_wR_factor_gt          0.0761
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.106
_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
C1 C 0.35950(19) 0.6439(5) 0.31830(15) 0.0227(8) Uani 1 1 d . . .
C2 C 0.3787(2) 0.4899(5) 0.35535(16) 0.0236(8) Uani 1 1 d . . .
C3 C 0.3506(2) 0.3142(6) 0.34347(15) 0.0250(8) Uani 1 1 d . . .
C4 C 0.3754(2) 0.1807(6) 0.38243(17) 0.0345(10) Uani 1 1 d . . .
H4 H 0.3591 0.0639 0.3757 0.041 Uiso 1 1 calc R . .
C5 C 0.4229(3) 0.2174(6) 0.43010(17) 0.0376(11) Uani 1 1 d . . .
H5 H 0.4382 0.1251 0.4545 0.045 Uiso 1 1 calc R . .
C6 C 0.4483(2) 0.3910(6) 0.44225(16) 0.0302(9) Uani 1 1 d . . .
C7 C 0.4265(2) 0.5243(5) 0.40414(16) 0.0265(9) Uani 1 1 d . . .
H7 H 0.4441 0.6398 0.4113 0.032 Uiso 1 1 calc R . .
C8 C 0.2158(2) 0.8011(6) 0.35074(16) 0.0302(9) Uani 1 1 d . . .
C9 C 0.2015(2) 0.8410(6) 0.40357(16) 0.0321(10) Uani 1 1 d . . .
C10 C 0.1668(3) 0.7156(7) 0.42838(19) 0.0396(11) Uani 1 1 d . . .
C11 C 0.1525(3) 0.7567(8) 0.4769(2) 0.0489(13) Uani 1 1 d . . .
H11 H 0.1284 0.6755 0.4925 0.059 Uiso 1 1 calc R . .
C12 C 0.1740(3) 0.9174(8) 0.5017(2) 0.0500(13) Uani 1 1 d . . .
H12 H 0.1645 0.9440 0.5341 0.060 Uiso 1 1 calc R . .
C13 C 0.2100(3) 1.0408(6) 0.47892(19) 0.0391(11) Uani 1 1 d . . .
C14 C 0.2227(3) 1.0034(6) 0.42954(18) 0.0362(10) Uani 1 1 d . . .
H14 H 0.2455 1.0875 0.4138 0.043 Uiso 1 1 calc R . .
C16 C 0.4459(11) 1.2085(16) 0.2703(7) 0.251(10) Uani 1 1 d DU . .
H16 H 0.4496 1.2348 0.3061 0.301 Uiso 1 1 calc R . .
C17 C 0.4680(12) 1.347(2) 0.1740(5) 0.249(9) Uani 1 1 d DU . .
C18 C 0.5000 1.5557(12) 0.2500 0.53(5) Uani 1 2 d SDU . .
H1M H 0.1554 0.5535 0.3758 0.634 Uiso 1 1 d RD . .
H1W H 0.3280 0.6614 0.1745 0.634 Uiso 1 1 d RD . .
H2W H 0.3772 0.7621 0.1725 0.634 Uiso 1 1 d RD . .
H3W H 0.4902 0.8805 0.3435 0.634 Uiso 1 1 d RD . .
H4W H 0.5484 0.9204 0.3717 0.634 Uiso 1 1 d RD . .
La1 La 0.298116(11) 0.96428(3) 0.251183(8) 0.02007(10) Uani 1 1 d . . .
N1 N 0.4933(2) 0.4194(5) 0.49420(14) 0.0341(8) Uani 1 1 d . . .
N2 N 0.2312(2) 1.2003(6) 0.50919(16) 0.0452(10) Uani 1 1 d . . .
N3 N 0.4744(12) 1.3587(18) 0.2369(6) 0.300(11) Uani 1 1 d DU . .
O1 O 0.23782(17) 0.9248(4) 0.32634(11) 0.0326(7) Uani 1 1 d . . .
O2 O 0.39067(16) 0.7916(4) 0.32779(12) 0.0373(8) Uani 1 1 d . . .
O3 O 0.1474(2) 0.5521(5) 0.40623(15) 0.0527(10) Uani 1 1 d D . .
O4 O 0.30969(14) 0.6310(4) 0.27595(11) 0.0274(6) Uani 1 1 d . . .
O5 O 0.30329(15) 0.2717(4) 0.29835(11) 0.0286(6) Uani 1 1 d . . .
O6 O 0.3400(2) 0.7696(5) 0.18154(16) 0.0582(11) Uani 1 1 d D . .
O7 O 0.5319(2) 0.8663(8) 0.34217(19) 0.0794(14) Uani 1 1 d D . .
O8 O 0.4199(3) 1.0632(13) 0.2542(2) 0.137(4) Uani 1 1 d D . .
O9 O 0.2048(2) 0.6425(4) 0.33292(13) 0.0453(9) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O2 1.258(5) . ?
C1 O4 1.283(5) . ?
C1 C2 1.481(5) . ?
C1 La1 3.020(4) . ?
C2 C7 1.398(5) . ?
C2 C3 1.426(6) . ?
C3 O5 1.340(5) . ?
C3 C4 1.411(6) . ?
C4 C5 1.378(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.396(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.388(6) . ?
C6 N1 1.429(5) . ?
C7 H7 0.9300 . ?
C8 O1 1.259(5) . ?
C8 O9 1.266(5) . ?
C8 C9 1.498(6) . ?
C9 C14 1.396(6) . ?
C9 C10 1.414(6) . ?
C10 O3 1.359(6) . ?
C10 C11 1.392(7) . ?
C11 C12 1.373(8) . ?
C11 H11 0.9300 . ?
C12 C13 1.390(8) . ?
C12 H12 0.9300 . ?
C13 C14 1.394(7) . ?
C13 N2 1.426(6) . ?
C14 H14 0.9300 . ?
C16 O8 1.227(9) . ?
C16 N3 1.607(9) . ?
C16 H16 0.9300 . ?
C17 N3 1.601(9) . ?
C18 N3 1.562(9) . ?
C18 N3 1.562(9) 2_655 ?
La1 O4 2.439(3) 4 ?
La1 O9 2.536(3) 4 ?
La1 O8 2.538(5) . ?
La1 O5 2.551(3) 4 ?
La1 O4 2.558(3) . ?
La1 O1 2.560(3) . ?
La1 O5 2.583(3) 1_565 ?
La1 O6 2.614(3) . ?
La1 O2 2.672(3) . ?
La1 La1 4.1883(5) 4_545 ?
La1 La1 4.1883(4) 4 ?
N1 N1 1.249(7) 5_666 ?
N2 N2 1.236(9) 7_576 ?
N3 N3 1.08(4) 2_655 ?
O3 H1M 0.8446 . ?
O4 La1 2.439(3) 4_545 ?
O5 La1 2.551(3) 4_545 ?
O5 La1 2.583(3) 1_545 ?
O6 H1W 0.8469 . ?
O6 H2W 0.8409 . ?
O7 H3W 0.8533 . ?
O7 H4W 0.8526 . ?
O9 La1 2.536(3) 4_545 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 C1 O4 118.2(3) . . ?
O2 C1 C2 121.1(3) . . ?
O4 C1 C2 120.7(3) . . ?
O2 C1 La1 62.0(2) . . ?
O4 C1 La1 56.97(19) . . ?
C2 C1 La1 169.6(3) . . ?
C7 C2 C3 120.3(4) . . ?
C7 C2 C1 116.5(4) . . ?
C3 C2 C1 123.2(3) . . ?
O5 C3 C4 119.7(4) . . ?
O5 C3 C2 123.9(3) . . ?
C4 C3 C2 116.4(3) . . ?
C5 C4 C3 122.3(4) . . ?
C5 C4 H4 118.8 . . ?
C3 C4 H4 118.8 . . ?
C4 C5 C6 120.9(4) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C7 C6 C5 118.2(4) . . ?
C7 C6 N1 124.7(4) . . ?
C5 C6 N1 117.1(4) . . ?
C6 C7 C2 121.9(4) . . ?
C6 C7 H7 119.1 . . ?
C2 C7 H7 119.1 . . ?
O1 C8 O9 123.4(4) . . ?
O1 C8 C9 119.2(4) . . ?
O9 C8 C9 117.4(4) . . ?
C14 C9 C10 118.6(4) . . ?
C14 C9 C8 120.3(4) . . ?
C10 C9 C8 121.1(4) . . ?
O3 C10 C11 118.2(4) . . ?
O3 C10 C9 121.5(4) . . ?
C11 C10 C9 120.3(4) . . ?
C12 C11 C10 119.9(5) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C11 C12 C13 120.9(5) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C12 C13 C14 119.6(4) . . ?
C12 C13 N2 115.7(4) . . ?
C14 C13 N2 124.7(5) . . ?
C9 C14 C13 120.6(4) . . ?
C9 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
O8 C16 N3 127.6(12) . . ?
O8 C16 H16 116.2 . . ?
N3 C16 H16 116.2 . . ?
N3 C18 N3 40.3(17) . 2_655 ?
O4 La1 O9 70.40(11) 4 4 ?
O4 La1 O8 129.8(2) 4 . ?
O9 La1 O8 71.52(17) 4 . ?
O4 La1 O5 66.76(9) 4 4 ?
O9 La1 O5 91.40(11) 4 4 ?
O8 La1 O5 144.9(2) . 4 ?
O4 La1 O4 125.62(7) 4 . ?
O9 La1 O4 134.66(10) 4 . ?
O8 La1 O4 104.4(2) . . ?
O5 La1 O4 65.80(8) 4 . ?
O4 La1 O1 73.56(10) 4 . ?
O9 La1 O1 143.22(11) 4 . ?
O8 La1 O1 130.70(15) . . ?
O5 La1 O1 80.98(10) 4 . ?
O4 La1 O1 74.26(10) . . ?
O4 La1 O5 67.02(9) 4 1_565 ?
O9 La1 O5 86.04(10) 4 1_565 ?
O8 La1 O5 78.9(2) . 1_565 ?
O5 La1 O5 131.67(5) 4 1_565 ?
O4 La1 O5 138.68(9) . 1_565 ?
O1 La1 O5 73.27(10) . 1_565 ?
O4 La1 O6 120.25(12) 4 . ?
O9 La1 O6 68.85(11) 4 . ?
O8 La1 O6 72.7(2) . . ?
O5 La1 O6 72.54(12) 4 . ?
O4 La1 O6 67.07(11) . . ?
O1 La1 O6 139.42(11) . . ?
O5 La1 O6 146.69(11) 1_565 . ?
O4 La1 O2 148.83(10) 4 . ?
O9 La1 O2 138.20(12) 4 . ?
O8 La1 O2 68.61(17) . . ?
O5 La1 O2 114.57(9) 4 . ?
O4 La1 O2 49.21(9) . . ?
O1 La1 O2 75.95(11) . . ?
O5 La1 O2 98.07(9) 1_565 . ?
O6 La1 O2 87.60(12) . . ?
O4 La1 C1 140.23(10) 4 . ?
O9 La1 C1 145.29(11) 4 . ?
O8 La1 C1 87.9(2) . . ?
O5 La1 C1 90.01(9) 4 . ?
O4 La1 C1 24.87(9) . . ?
O1 La1 C1 71.11(11) . . ?
O5 La1 C1 117.86(9) 1_565 . ?
O6 La1 C1 78.58(11) . . ?
O2 La1 C1 24.57(10) . . ?
O4 La1 La1 94.31(7) 4 4_545 ?
O9 La1 La1 122.96(9) 4 4_545 ?
O8 La1 La1 134.2(2) . 4_545 ?
O5 La1 La1 35.58(6) 4 4_545 ?
O4 La1 La1 32.17(6) . 4_545 ?
O1 La1 La1 66.52(7) . 4_545 ?
O5 La1 La1 139.16(7) 1_565 4_545 ?
O6 La1 La1 74.15(8) . 4_545 ?
O2 La1 La1 79.29(6) . 4_545 ?
C1 La1 La1 54.93(7) . 4_545 ?
O4 La1 La1 33.95(6) 4 4 ?
O9 La1 La1 67.30(7) 4 4 ?
O8 La1 La1 100.4(2) . 4 ?
O5 La1 La1 100.70(6) 4 4 ?
O4 La1 La1 151.34(7) . 4 ?
O1 La1 La1 78.78(7) . 4 ?
O5 La1 La1 35.08(6) 1_565 4 ?
O6 La1 La1 135.40(9) . 4 ?
O2 La1 La1 132.00(7) . 4 ?
C1 La1 La1 146.00(7) . 4 ?
La1 La1 La1 125.423(13) 4_545 4 ?
N1 N1 C6 114.4(4) 5_666 . ?
N2 N2 C13 114.4(5) 7_576 . ?
N3 N3 C18 69.8(8) 2_655 . ?
N3 N3 C17 117(3) 2_655 . ?
C18 N3 C17 102.1(7) . . ?
N3 N3 C16 94.3(13) 2_655 . ?
C18 N3 C16 132.8(9) . . ?
C17 N3 C16 124.2(8) . . ?
C8 O1 La1 139.5(3) . . ?
C1 O2 La1 93.4(2) . . ?
C10 O3 H1M 106.2 . . ?
C1 O4 La1 136.4(3) . 4_545 ?
C1 O4 La1 98.2(2) . . ?
La1 O4 La1 113.88(10) 4_545 . ?
C3 O5 La1 126.9(2) . 4_545 ?
C3 O5 La1 123.6(2) . 1_545 ?
La1 O5 La1 109.33(9) 4_545 1_545 ?
La1 O6 H1W 123.4 . . ?
La1 O6 H2W 134.1 . . ?
H1W O6 H2W 95.8 . . ?
H3W O7 H4W 93.8 . . ?
C16 O8 La1 126.2(12) . . ?
C8 O9 La1 139.8(3) . 4_545 ?

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
O2 C1 C2 C7 8.1(6) . . . . ?
O4 C1 C2 C7 -170.7(4) . . . . ?
La1 C1 C2 C7 -96.7(15) . . . . ?
O2 C1 C2 C3 -172.5(4) . . . . ?
O4 C1 C2 C3 8.7(6) . . . . ?
La1 C1 C2 C3 82.7(15) . . . . ?
C7 C2 C3 O5 178.0(4) . . . . ?
C1 C2 C3 O5 -1.4(7) . . . . ?
C7 C2 C3 C4 -2.0(6) . . . . ?
C1 C2 C3 C4 178.6(4) . . . . ?
O5 C3 C4 C5 -178.5(5) . . . . ?
C2 C3 C4 C5 1.6(7) . . . . ?
C3 C4 C5 C6 0.7(8) . . . . ?
C4 C5 C6 C7 -2.4(8) . . . . ?
C4 C5 C6 N1 175.4(5) . . . . ?
C5 C6 C7 C2 1.9(7) . . . . ?
N1 C6 C7 C2 -175.7(4) . . . . ?
C3 C2 C7 C6 0.3(7) . . . . ?
C1 C2 C7 C6 179.7(4) . . . . ?
O1 C8 C9 C14 -10.5(7) . . . . ?
O9 C8 C9 C14 169.7(5) . . . . ?
O1 C8 C9 C10 170.0(4) . . . . ?
O9 C8 C9 C10 -9.8(7) . . . . ?
C14 C9 C10 O3 -177.3(5) . . . . ?
C8 C9 C10 O3 2.3(8) . . . . ?
C14 C9 C10 C11 1.9(8) . . . . ?
C8 C9 C10 C11 -178.5(5) . . . . ?
O3 C10 C11 C12 177.1(5) . . . . ?
C9 C10 C11 C12 -2.1(9) . . . . ?
C10 C11 C12 C13 0.2(9) . . . . ?
C11 C12 C13 C14 1.8(9) . . . . ?
C11 C12 C13 N2 -178.3(5) . . . . ?
C10 C9 C14 C13 0.1(8) . . . . ?
C8 C9 C14 C13 -179.5(5) . . . . ?
C12 C13 C14 C9 -2.0(8) . . . . ?
N2 C13 C14 C9 178.2(5) . . . . ?
O2 C1 La1 O4 -126.1(3) . . . 4 ?
O4 C1 La1 O4 64.7(3) . . . 4 ?
C2 C1 La1 O4 -15.6(15) . . . 4 ?
O2 C1 La1 O9 89.5(3) . . . 4 ?
O4 C1 La1 O9 -79.7(3) . . . 4 ?
C2 C1 La1 O9 -160.1(14) . . . 4 ?
O2 C1 La1 O8 37.0(3) . . . . ?
O4 C1 La1 O8 -132.1(3) . . . . ?
C2 C1 La1 O8 147.5(15) . . . . ?
O2 C1 La1 O5 -178.0(3) . . . 4 ?
O4 C1 La1 O5 12.8(2) . . . 4 ?
C2 C1 La1 O5 -67.6(15) . . . 4 ?
O2 C1 La1 O4 169.2(4) . . . . ?
C2 C1 La1 O4 -80.4(15) . . . . ?
O2 C1 La1 O1 -97.6(3) . . . . ?
O4 C1 La1 O1 93.3(2) . . . . ?
C2 C1 La1 O1 12.9(15) . . . . ?
O2 C1 La1 O5 -39.2(3) . . . 1_565 ?
O4 C1 La1 O5 151.6(2) . . . 1_565 ?
C2 C1 La1 O5 71.2(15) . . . 1_565 ?
O2 C1 La1 O6 109.8(3) . . . . ?
O4 C1 La1 O6 -59.4(2) . . . . ?
C2 C1 La1 O6 -139.7(15) . . . . ?
O4 C1 La1 O2 -169.2(4) . . . . ?
C2 C1 La1 O2 110.4(15) . . . . ?
O2 C1 La1 La1 -171.6(3) . . . 4_545 ?
O4 C1 La1 La1 19.2(2) . . . 4_545 ?
C2 C1 La1 La1 -61.2(15) . . . 4_545 ?
O2 C1 La1 La1 -68.6(3) . . . 4 ?
O4 C1 La1 La1 122.2(2) . . . 4 ?
C2 C1 La1 La1 41.8(15) . . . 4 ?
C7 C6 N1 N1 7.3(8) . . . 5_666 ?
C5 C6 N1 N1 -170.3(5) . . . 5_666 ?
C12 C13 N2 N2 173.3(6) . . . 7_576 ?
C14 C13 N2 N2 -6.9(9) . . . 7_576 ?
N3 C18 N3 C17 -115(3) 2_655 . . . ?
N3 C18 N3 C16 77(2) 2_655 . . . ?
O8 C16 N3 N3 -122(2) . . . 2_655 ?
O8 C16 N3 C18 171.2(17) . . . . ?
O8 C16 N3 C17 5(4) . . . . ?
O9 C8 O1 La1 -17.8(8) . . . . ?
C9 C8 O1 La1 162.4(3) . . . . ?
O4 La1 O1 C8 122.1(4) 4 . . . ?
O9 La1 O1 C8 134.0(4) 4 . . . ?
O8 La1 O1 C8 -109.1(5) . . . . ?
O5 La1 O1 C8 53.8(4) 4 . . . ?
O4 La1 O1 C8 -13.5(4) . . . . ?
O5 La1 O1 C8 -167.5(5) 1_565 . . . ?
O6 La1 O1 C8 4.5(5) . . . . ?
O2 La1 O1 C8 -64.5(4) . . . . ?
C1 La1 O1 C8 -39.3(4) . . . . ?
La1 La1 O1 C8 19.8(4) 4_545 . . . ?
La1 La1 O1 C8 156.7(4) 4 . . . ?
O4 C1 O2 La1 10.3(4) . . . . ?
C2 C1 O2 La1 -168.6(3) . . . . ?
O4 La1 O2 C1 87.5(3) 4 . . . ?
O9 La1 O2 C1 -121.3(3) 4 . . . ?
O8 La1 O2 C1 -139.7(4) . . . . ?
O5 La1 O2 C1 2.2(3) 4 . . . ?
O4 La1 O2 C1 -6.0(2) . . . . ?
O1 La1 O2 C1 75.2(3) . . . . ?
O5 La1 O2 C1 145.6(3) 1_565 . . . ?
O6 La1 O2 C1 -67.4(3) . . . . ?
La1 La1 O2 C1 7.0(2) 4_545 . . . ?
La1 La1 O2 C1 135.5(2) 4 . . . ?
O2 C1 O4 La1 -148.9(3) . . . 4_545 ?
C2 C1 O4 La1 30.1(6) . . . 4_545 ?
La1 C1 O4 La1 -138.0(4) . . . 4_545 ?
O2 C1 O4 La1 -10.8(4) . . . . ?
C2 C1 O4 La1 168.1(3) . . . . ?
O4 La1 O4 C1 -134.6(3) 4 . . . ?
O9 La1 O4 C1 128.0(3) 4 . . . ?
O8 La1 O4 C1 49.9(3) . . . . ?
O5 La1 O4 C1 -166.0(3) 4 . . . ?
O1 La1 O4 C1 -78.9(2) . . . . ?
O5 La1 O4 C1 -39.6(3) 1_565 . . . ?
O6 La1 O4 C1 113.7(3) . . . . ?
O2 La1 O4 C1 5.9(2) . . . . ?
La1 La1 O4 C1 -149.7(3) 4_545 . . . ?
La1 La1 O4 C1 -99.4(2) 4 . . . ?
O4 La1 O4 La1 15.07(9) 4 . . 4_545 ?
O9 La1 O4 La1 -82.28(19) 4 . . 4_545 ?
O8 La1 O4 La1 -160.40(18) . . . 4_545 ?
O5 La1 O4 La1 -16.26(11) 4 . . 4_545 ?
O1 La1 O4 La1 70.77(13) . . . 4_545 ?
O5 La1 O4 La1 110.09(14) 1_565 . . 4_545 ?
O6 La1 O4 La1 -96.64(15) . . . 4_545 ?
O2 La1 O4 La1 155.60(19) . . . 4_545 ?
C1 La1 O4 La1 149.7(3) . . . 4_545 ?
La1 La1 O4 La1 50.29(19) 4 . . 4_545 ?
C4 C3 O5 La1 141.8(3) . . . 4_545 ?
C2 C3 O5 La1 -38.3(6) . . . 4_545 ?
C4 C3 O5 La1 -34.3(5) . . . 1_545 ?
C2 C3 O5 La1 145.7(3) . . . 1_545 ?
N3 C16 O8 La1 -118(2) . . . . ?
O4 La1 O8 C16 42.4(12) 4 . . . ?
O9 La1 O8 C16 84.8(12) 4 . . . ?
O5 La1 O8 C16 149.3(11) 4 . . . ?
O4 La1 O8 C16 -142.4(12) . . . . ?
O1 La1 O8 C16 -60.9(13) . . . . ?
O5 La1 O8 C16 -4.7(12) 1_565 . . . ?
O6 La1 O8 C16 157.7(12) . . . . ?
O2 La1 O8 C16 -108.0(12) . . . . ?
C1 La1 O8 C16 -123.6(12) . . . . ?
La1 La1 O8 C16 -156.8(12) 4_545 . . . ?
La1 La1 O8 C16 23.2(12) 4 . . . ?
O1 C8 O9 La1 -7.7(8) . . . 4_545 ?
C9 C8 O9 La1 172.1(3) . . . 4_545 ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.591
_refine_diff_density_min         -1.116
_refine_diff_density_rms         0.113
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_p2015110915shense_0m
_audit_block_doi                 10.5517/ccdc.csd.cc1nllpj
_database_code_depnum_ccdc_archive 'CCDC 1537218'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C7CC01898C 2017
_audit_update_record             
;
2017-03-10 deposited with the CCDC.
2017-06-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H16 Gd N3 O9'
_chemical_formula_weight         563.58

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Gd Gd -0.1653 3.9035 '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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.8181(2)
_cell_length_b                   8.78790(10)
_cell_length_c                   27.5387(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.1830(10)
_cell_angle_gamma                90.00
_cell_volume                     2085.98(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9955
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      27.64

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.795
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1100
_exptl_absorpt_coefficient_mu    3.232
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.7381
_exptl_absorpt_correction_T_max  0.9093
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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            14116
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_av_sigmaI/netI    0.0192
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         1.51
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3689
_reflns_number_gt                3402
_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)+(0.0364P)²+0.3324P] 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         3689
_refine_ls_number_parameters     285
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0215
_refine_ls_R_factor_gt           0.0178
_refine_ls_wR_factor_ref         0.0626
_refine_ls_wR_factor_gt          0.0504
_refine_ls_goodness_of_fit_ref   1.253
_refine_ls_restrained_S_all      1.253
_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
C1 C 0.5599(4) 0.2529(3) 0.66486(10) 0.0248(7) Uani 1 1 d . . .
C2 C 0.5838(4) 0.2729(3) 0.61349(11) 0.0279(7) Uani 1 1 d . . .
C3 C 0.5372(4) 0.1595(4) 0.57871(11) 0.0298(7) Uani 1 1 d . . .
H3 H 0.4881 0.0732 0.5875 0.036 Uiso 1 1 calc R . .
C4 C 0.5630(4) 0.1732(4) 0.53088(11) 0.0354(8) Uani 1 1 d . . .
C5 C 0.6322(5) 0.3043(5) 0.51786(13) 0.0547(11) Uani 1 1 d . . .
H5 H 0.6473 0.3153 0.4856 0.066 Uiso 1 1 calc R . .
C6 C 0.6787(6) 0.4177(5) 0.55177(15) 0.0587(13) Uani 1 1 d . . .
H6 H 0.7258 0.5047 0.5425 0.070 Uiso 1 1 calc R . .
C7 C 0.6558(5) 0.4035(4) 0.59968(13) 0.0427(9) Uani 1 1 d . . .
C8 C 0.3425(3) 0.6873(3) 0.67507(10) 0.0206(6) Uani 1 1 d . . .
C9 C 0.2571(4) 0.5649(3) 0.64393(11) 0.0212(6) Uani 1 1 d . . .
C10 C 0.2364(4) 0.4167(3) 0.66178(11) 0.0243(7) Uani 1 1 d . . .
C11 C 0.1549(4) 0.3108(4) 0.62769(11) 0.0390(9) Uani 1 1 d . . .
H11 H 0.1436 0.2119 0.6384 0.047 Uiso 1 1 calc R . .
C12 C 0.0919(4) 0.3474(4) 0.57955(12) 0.0408(9) Uani 1 1 d . . .
H12 H 0.0400 0.2738 0.5580 0.049 Uiso 1 1 calc R . .
C13 C 0.1054(4) 0.4961(4) 0.56243(10) 0.0270(7) Uani 1 1 d . . .
C14 C 0.1891(4) 0.6006(3) 0.59450(11) 0.0247(7) Uani 1 1 d . . .
H14 H 0.2010 0.6984 0.5830 0.030 Uiso 1 1 calc R . .
C22 C 0.3053(4) 0.3474(4) 0.85461(13) 0.0358(8) Uani 1 1 d . . .
H22 H 0.3953 0.3135 0.8758 0.043 Uiso 1 1 calc R . .
C27 C 0.1846(6) 0.3369(6) 0.92549(16) 0.0704(14) Uani 1 1 d . . .
H27A H 0.2844 0.2985 0.9417 0.106 Uiso 1 1 calc R . .
H27B H 0.1065 0.2622 0.9273 0.106 Uiso 1 1 calc R . .
H27C H 0.1628 0.4286 0.9417 0.106 Uiso 1 1 calc R . .
C28 C 0.0457(8) 0.4271(10) 0.8442(3) 0.147(4) Uani 1 1 d . . .
H28A H 0.0679 0.5172 0.8273 0.221 Uiso 1 1 calc R . .
H28B H -0.0251 0.4515 0.8652 0.221 Uiso 1 1 calc R . .
H28C H -0.0001 0.3519 0.8203 0.221 Uiso 1 1 calc R . .
Gd1 Gd 0.503854(15) 0.438285(14) 0.766810(4) 0.01824(7) Uani 1 1 d . . .
H1M H 0.670(4) 0.500(5) 0.6579(9) 0.048(11) Uiso 1 1 d D . .
H1W H 0.753(4) 0.6661(16) 0.7763(14) 0.061(13) Uiso 1 1 d D . .
H2W H 0.812(4) 0.567(4) 0.7529(14) 0.048(13) Uiso 1 1 d D . .
N1 N 0.5242(4) 0.0612(3) 0.49315(11) 0.0396(8) Uani 1 1 d . . .
N2 N 0.0378(3) 0.5491(3) 0.51422(10) 0.0298(6) Uani 1 1 d . . .
N3 N 0.1850(4) 0.3691(4) 0.87361(11) 0.0449(7) Uani 1 1 d . . .
O1 O 0.9848(6) 0.5136(12) 0.7218(2) 0.172(3) Uani 1 1 d . . .
O2 O 0.3107(3) 0.3679(3) 0.81080(9) 0.0446(6) Uani 1 1 d . . .
O3 O 0.4994(3) 0.1324(2) 0.67557(7) 0.0323(5) Uani 1 1 d . . .
O4 O 0.7435(3) 0.5721(2) 0.77004(9) 0.0315(5) Uani 1 1 d D . .
O5 O 0.3351(3) 0.8213(2) 0.65927(7) 0.0329(5) Uani 1 1 d . . .
O6 O 0.6013(3) 0.3620(2) 0.69562(8) 0.0313(5) Uani 1 1 d . . .
O7 O 0.2837(2) 0.3767(2) 0.70875(7) 0.0269(5) Uani 1 1 d . . .
O8 O 0.4260(2) 0.6594(2) 0.71798(7) 0.0250(5) Uani 1 1 d . . .
O9 O 0.7050(4) 0.5170(3) 0.63210(10) 0.0636(9) Uani 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
C1 O3 1.249(4) . ?
C1 O6 1.280(3) . ?
C1 C2 1.484(4) . ?
C2 C3 1.383(4) . ?
C2 C7 1.402(5) . ?
C3 C4 1.389(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.385(5) . ?
C4 N1 1.420(4) . ?
C5 C6 1.369(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.382(5) . ?
C6 H6 0.9300 . ?
C7 O9 1.347(4) . ?
C8 O5 1.253(3) . ?
C8 O8 1.277(3) . ?
C8 C9 1.479(4) . ?
C8 Gd1 2.889(3) 2_656 ?
C9 C14 1.402(4) . ?
C9 C10 1.418(4) . ?
C10 O7 1.320(3) . ?
C10 C11 1.407(4) . ?
C11 C12 1.364(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.402(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.376(4) . ?
C13 N2 1.415(4) . ?
C14 H14 0.9300 . ?
C22 O2 1.231(4) . ?
C22 N3 1.292(5) . ?
C22 H22 0.9300 . ?
C27 N3 1.457(5) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 N3 1.415(7) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
Gd1 O7 2.3040(19) . ?
Gd1 O3 2.334(2) 2_656 ?
Gd1 O2 2.371(2) . ?
Gd1 O8 2.3803(18) . ?
Gd1 O6 2.396(2) . ?
Gd1 O4 2.404(2) . ?
Gd1 O5 2.4489(18) 2_646 ?
Gd1 O8 2.5406(19) 2_646 ?
Gd1 C8 2.889(3) 2_646 ?
N1 N1 1.245(5) 3_656 ?
N2 N2 1.258(5) 3_566 ?
O3 Gd1 2.334(2) 2_646 ?
O4 H1W 0.845(10) . ?
O4 H2W 0.840(10) . ?
O5 Gd1 2.4489(18) 2_656 ?
O8 Gd1 2.5406(19) 2_656 ?
O9 H1M 0.846(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 C1 O6 123.7(3) . . ?
O3 C1 C2 118.6(3) . . ?
O6 C1 C2 117.6(3) . . ?
C3 C2 C7 119.2(3) . . ?
C3 C2 C1 119.6(3) . . ?
C7 C2 C1 121.3(3) . . ?
C2 C3 C4 120.7(3) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 119.1(3) . . ?
C5 C4 N1 116.0(3) . . ?
C3 C4 N1 124.9(3) . . ?
C6 C5 C4 120.9(3) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C7 120.2(4) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
O9 C7 C6 118.3(3) . . ?
O9 C7 C2 121.8(3) . . ?
C6 C7 C2 119.9(3) . . ?
O5 C8 O8 118.7(2) . . ?
O5 C8 C9 120.0(2) . . ?
O8 C8 C9 121.4(2) . . ?
O5 C8 Gd1 57.22(13) . 2_656 ?
O8 C8 Gd1 61.48(14) . 2_656 ?
C9 C8 Gd1 176.76(19) . 2_656 ?
C14 C9 C10 118.8(3) . . ?
C14 C9 C8 117.5(2) . . ?
C10 C9 C8 123.7(3) . . ?
O7 C10 C11 119.3(3) . . ?
O7 C10 C9 123.2(3) . . ?
C11 C10 C9 117.5(3) . . ?
C12 C11 C10 122.6(3) . . ?
C12 C11 H11 118.7 . . ?
C10 C11 H11 118.7 . . ?
C11 C12 C13 120.1(3) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C14 C13 C12 118.6(3) . . ?
C14 C13 N2 116.4(3) . . ?
C12 C13 N2 125.0(3) . . ?
C13 C14 C9 122.4(3) . . ?
C13 C14 H14 118.8 . . ?
C9 C14 H14 118.8 . . ?
O2 C22 N3 125.5(3) . . ?
O2 C22 H22 117.2 . . ?
N3 C22 H22 117.2 . . ?
N3 C27 H27A 109.5 . . ?
N3 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
N3 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
N3 C28 H28A 109.5 . . ?
N3 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
N3 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
O7 Gd1 O3 120.95(8) . 2_656 ?
O7 Gd1 O2 72.69(8) . . ?
O3 Gd1 O2 74.35(9) 2_656 . ?
O7 Gd1 O8 72.52(7) . . ?
O3 Gd1 O8 75.17(7) 2_656 . ?
O2 Gd1 O8 110.44(9) . . ?
O7 Gd1 O6 76.20(8) . . ?
O3 Gd1 O6 144.95(8) 2_656 . ?
O2 Gd1 O6 139.92(8) . . ?
O8 Gd1 O6 82.92(7) . . ?
O7 Gd1 O4 138.25(8) . . ?
O3 Gd1 O4 75.76(8) 2_656 . ?
O2 Gd1 O4 146.05(9) . . ?
O8 Gd1 O4 76.58(8) . . ?
O6 Gd1 O4 72.72(8) . . ?
O7 Gd1 O5 137.24(7) . 2_646 ?
O3 Gd1 O5 80.20(7) 2_656 2_646 ?
O2 Gd1 O5 79.57(9) . 2_646 ?
O8 Gd1 O5 149.28(7) . 2_646 ?
O6 Gd1 O5 108.50(8) . 2_646 ?
O4 Gd1 O5 79.83(8) . 2_646 ?
O7 Gd1 O8 91.59(7) . 2_646 ?
O3 Gd1 O8 129.07(6) 2_656 2_646 ?
O2 Gd1 O8 80.79(9) . 2_646 ?
O8 Gd1 O8 155.75(3) . 2_646 ?
O6 Gd1 O8 75.41(7) . 2_646 ?
O4 Gd1 O8 106.52(7) . 2_646 ?
O5 Gd1 O8 51.67(6) 2_646 2_646 ?
O7 Gd1 C8 115.65(7) . 2_646 ?
O3 Gd1 C8 104.64(7) 2_656 2_646 ?
O2 Gd1 C8 79.69(9) . 2_646 ?
O8 Gd1 C8 169.06(8) . 2_646 ?
O6 Gd1 C8 91.86(8) . 2_646 ?
O4 Gd1 C8 92.71(8) . 2_646 ?
O5 Gd1 C8 25.47(7) 2_646 2_646 ?
O8 Gd1 C8 26.21(7) 2_646 2_646 ?
N1 N1 C4 115.0(4) 3_656 . ?
N2 N2 C13 114.9(3) 3_566 . ?
C22 N3 C28 120.6(4) . . ?
C22 N3 C27 122.7(4) . . ?
C28 N3 C27 116.7(4) . . ?
C22 O2 Gd1 136.1(2) . . ?
C1 O3 Gd1 147.93(19) . 2_646 ?
Gd1 O4 H1W 123(2) . . ?
Gd1 O4 H2W 133(3) . . ?
H1W O4 H2W 96.3(14) . . ?
C8 O5 Gd1 97.31(15) . 2_656 ?
C1 O6 Gd1 130.49(19) . . ?
C10 O7 Gd1 131.53(19) . . ?
C8 O8 Gd1 136.09(18) . . ?
C8 O8 Gd1 92.30(16) . 2_656 ?
Gd1 O8 Gd1 131.55(8) . 2_656 ?
C7 O9 H1M 107(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 C1 C2 C3 0.8(5) . . . . ?
O6 C1 C2 C3 -178.4(3) . . . . ?
O3 C1 C2 C7 -177.9(3) . . . . ?
O6 C1 C2 C7 2.9(5) . . . . ?
C7 C2 C3 C4 0.9(5) . . . . ?
C1 C2 C3 C4 -177.8(3) . . . . ?
C2 C3 C4 C5 -1.9(5) . . . . ?
C2 C3 C4 N1 177.9(3) . . . . ?
C3 C4 C5 C6 1.7(6) . . . . ?
N1 C4 C5 C6 -178.0(4) . . . . ?
C4 C5 C6 C7 -0.6(8) . . . . ?
C5 C6 C7 O9 179.2(5) . . . . ?
C5 C6 C7 C2 -0.4(8) . . . . ?
C3 C2 C7 O9 -179.3(4) . . . . ?
C1 C2 C7 O9 -0.6(6) . . . . ?
C3 C2 C7 C6 0.3(6) . . . . ?
C1 C2 C7 C6 179.0(4) . . . . ?
O5 C8 C9 C14 9.4(5) . . . . ?
O8 C8 C9 C14 -169.9(3) . . . . ?
Gd1 C8 C9 C14 38(4) 2_656 . . . ?
O5 C8 C9 C10 -168.5(3) . . . . ?
O8 C8 C9 C10 12.3(5) . . . . ?
Gd1 C8 C9 C10 -139(4) 2_656 . . . ?
C14 C9 C10 O7 -173.6(3) . . . . ?
C8 C9 C10 O7 4.2(5) . . . . ?
C14 C9 C10 C11 3.3(5) . . . . ?
C8 C9 C10 C11 -178.8(3) . . . . ?
O7 C10 C11 C12 174.7(4) . . . . ?
C9 C10 C11 C12 -2.4(6) . . . . ?
C10 C11 C12 C13 -0.8(6) . . . . ?
C11 C12 C13 C14 3.0(6) . . . . ?
C11 C12 C13 N2 -176.4(4) . . . . ?
C12 C13 C14 C9 -2.0(5) . . . . ?
N2 C13 C14 C9 177.4(3) . . . . ?
C10 C9 C14 C13 -1.2(5) . . . . ?
C8 C9 C14 C13 -179.2(3) . . . . ?
C5 C4 N1 N1 173.5(4) . . . 3_656 ?
C3 C4 N1 N1 -6.2(6) . . . 3_656 ?
C14 C13 N2 N2 179.9(4) . . . 3_566 ?
C12 C13 N2 N2 -0.7(6) . . . 3_566 ?
O2 C22 N3 C28 -2.8(7) . . . . ?
O2 C22 N3 C27 177.5(4) . . . . ?
N3 C22 O2 Gd1 150.1(3) . . . . ?
O7 Gd1 O2 C22 173.8(4) . . . . ?
O3 Gd1 O2 C22 -55.9(4) 2_656 . . . ?
O8 Gd1 O2 C22 -123.1(4) . . . . ?
O6 Gd1 O2 C22 133.1(3) . . . . ?
O4 Gd1 O2 C22 -26.8(4) . . . . ?
O5 Gd1 O2 C22 26.7(4) 2_646 . . . ?
O8 Gd1 O2 C22 79.2(4) 2_646 . . . ?
C8 Gd1 O2 C22 52.6(4) 2_646 . . . ?
O6 C1 O3 Gd1 -41.6(6) . . . 2_646 ?
C2 C1 O3 Gd1 139.3(3) . . . 2_646 ?
O8 C8 O5 Gd1 -2.6(3) . . . 2_656 ?
C9 C8 O5 Gd1 178.1(2) . . . 2_656 ?
O3 C1 O6 Gd1 -27.5(4) . . . . ?
C2 C1 O6 Gd1 151.7(2) . . . . ?
O7 Gd1 O6 C1 -40.5(2) . . . . ?
O3 Gd1 O6 C1 -165.4(2) 2_656 . . . ?
O2 Gd1 O6 C1 -0.7(3) . . . . ?
O8 Gd1 O6 C1 -114.2(3) . . . . ?
O4 Gd1 O6 C1 167.7(3) . . . . ?
O5 Gd1 O6 C1 95.1(3) 2_646 . . . ?
O8 Gd1 O6 C1 54.8(2) 2_646 . . . ?
C8 Gd1 O6 C1 75.4(3) 2_646 . . . ?
C11 C10 O7 Gd1 144.5(3) . . . . ?
C9 C10 O7 Gd1 -38.6(4) . . . . ?
O3 Gd1 O7 C10 97.5(3) 2_656 . . . ?
O2 Gd1 O7 C10 156.4(3) . . . . ?
O8 Gd1 O7 C10 37.6(3) . . . . ?
O6 Gd1 O7 C10 -49.2(3) . . . . ?
O4 Gd1 O7 C10 -6.4(3) . . . . ?
O5 Gd1 O7 C10 -151.6(2) 2_646 . . . ?
O8 Gd1 O7 C10 -123.7(3) 2_646 . . . ?
C8 Gd1 O7 C10 -134.5(2) 2_646 . . . ?
O5 C8 O8 Gd1 -175.0(2) . . . . ?
C9 C8 O8 Gd1 4.3(5) . . . . ?
Gd1 C8 O8 Gd1 -177.4(3) 2_656 . . . ?
O5 C8 O8 Gd1 2.5(3) . . . 2_656 ?
C9 C8 O8 Gd1 -178.2(3) . . . 2_656 ?
O7 Gd1 O8 C8 -21.0(3) . . . . ?
O3 Gd1 O8 C8 -150.9(3) 2_656 . . . ?
O2 Gd1 O8 C8 -84.3(3) . . . . ?
O6 Gd1 O8 C8 56.7(3) . . . . ?
O4 Gd1 O8 C8 130.5(3) . . . . ?
O5 Gd1 O8 C8 171.3(2) 2_646 . . . ?
O8 Gd1 O8 C8 30.0(3) 2_646 . . . ?
C8 Gd1 O8 C8 118.6(3) 2_646 . . . ?
O7 Gd1 O8 Gd1 162.41(14) . . . 2_656 ?
O3 Gd1 O8 Gd1 32.53(13) 2_656 . . 2_656 ?
O2 Gd1 O8 Gd1 99.18(13) . . . 2_656 ?
O6 Gd1 O8 Gd1 -119.88(13) . . . 2_656 ?
O4 Gd1 O8 Gd1 -46.02(12) . . . 2_656 ?
O5 Gd1 O8 Gd1 -5.2(2) 2_646 . . 2_656 ?
O8 Gd1 O8 Gd1 -146.51(13) 2_646 . . 2_656 ?
C8 Gd1 O8 Gd1 -58.0(4) 2_646 . . 2_656 ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.546
_refine_diff_density_min         -0.763
_refine_diff_density_rms         0.222
####################################################################### 
# 
# 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_p2015110913qian_0m
_audit_block_doi                 10.5517/ccdc.csd.cc1nlllf
_database_code_depnum_ccdc_archive 'CCDC 1537215'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C7CC01898C 2017
_audit_update_record             
;
2017-03-10 deposited with the CCDC.
2017-06-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16.50 H6 N3.50 O7.50 Sm'
_chemical_formula_weight         523.60

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sm Sm -0.1638 3.4418 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P1

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

_cell_length_a                   15.5354(8)
_cell_length_b                   15.8981(10)
_cell_length_c                   13.3111(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.592(3)
_cell_angle_gamma                90.00
_cell_volume                     3035.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8895
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      27.38

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.146
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1006
_exptl_absorpt_coefficient_mu    1.964
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.8278
_exptl_absorpt_correction_T_max  0.9434
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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            17320
_diffrn_reflns_av_R_equivalents  0.0765
_diffrn_reflns_av_sigmaI/netI    0.0815
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.28
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4832
_reflns_number_gt                3651
_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)+(0.0993P)²+43.3247P] 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         4832
_refine_ls_number_parameters     259
_refine_ls_number_restraints     32
_refine_ls_R_factor_all          0.1125
_refine_ls_R_factor_gt           0.0818
_refine_ls_wR_factor_ref         0.2345
_refine_ls_wR_factor_gt          0.2122
_refine_ls_goodness_of_fit_ref   1.164
_refine_ls_restrained_S_all      1.161
_refine_ls_shift/su_max          0.003
_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
C1 C 0.1050(9) 0.0447(9) 0.7250(10) 0.035(3) Uani 1 1 d . . .
C2 C 0.1968(9) 0.0291(9) 0.7852(10) 0.038(4) Uani 1 1 d . . .
H2 H 0.2163 0.0242 0.8603 0.045 Uiso 1 1 calc R . .
C3 C 0.2307(10) 0.0252(10) 0.6210(10) 0.039(4) Uani 1 1 d . . .
C4 C 0.1373(10) 0.0444(12) 0.5629(11) 0.053(5) Uani 1 1 d . . .
H4 H 0.1166 0.0515 0.4879 0.064 Uiso 1 1 calc R . .
C5 C 0.0752(10) 0.0533(11) 0.6113(11) 0.048(4) Uani 1 1 d . . .
H5 H 0.0130 0.0650 0.5694 0.058 Uiso 1 1 calc R . .
C6 C 0.4486(12) 0.2534(8) 0.5676(13) 0.047(4) Uani 1 1 d . . .
C7 C 0.2636(9) 0.0201(9) 0.7372(11) 0.034(3) Uani 1 1 d . . .
C8 C 0.4687(15) 0.4008(10) 0.5406(15) 0.068(5) Uani 1 1 d . . .
C9 C 0.4823(12) 0.3192(9) 0.5222(12) 0.051(4) Uani 1 1 d . . .
H9 H 0.5148 0.3063 0.4784 0.062 Uiso 1 1 calc R . .
C10 C 0.3594(8) 0.0039(8) 0.8063(9) 0.025(3) Uani 1 1 d . . .
C11 C 0.4665(10) 0.1621(9) 0.5428(11) 0.039(3) Uani 1 1 d . . .
C12 C 0.4171(19) 0.4182(11) 0.602(2) 0.101(9) Uani 1 1 d . . .
H12 H 0.4049 0.4741 0.6125 0.121 Uiso 1 1 calc R . .
C13 C 0.3830(18) 0.3566(12) 0.6484(19) 0.097(8) Uani 1 1 d . . .
H13 H 0.3481 0.3702 0.6893 0.116 Uiso 1 1 calc R . .
C14 C 0.4019(15) 0.2733(12) 0.6329(16) 0.074(6) Uani 1 1 d . . .
C15 C 0.5000 -0.216(4) 0.7500 0.17(2) Uani 1 2 d SU . .
C16 C 0.595(4) -0.340(3) 0.773(4) 0.24(2) Uani 1 1 d U . .
N1 N 0.5087(13) 0.4632(8) 0.4924(13) 0.067(4) Uani 1 1 d . . .
N2 N 0.0425(8) 0.0448(8) 0.7811(9) 0.044(3) Uani 1 1 d . . .
N4 N 0.5000 -0.308(4) 0.7500 0.21(2) Uani 1 2 d SU . .
O1 O 0.4452(6) 0.1087(6) 0.5950(7) 0.035(2) Uani 1 1 d . . .
O2 O 0.3686(11) 0.2138(8) 0.6786(12) 0.086(5) Uani 1 1 d . . .
O3 O 0.3870(6) 0.0105(6) 0.9091(6) 0.035(2) Uani 1 1 d . . .
O4 O 0.4998(8) 0.1505(6) 0.4715(8) 0.049(3) Uani 1 1 d . . .
O5 O 0.5000 -0.1558(11) 0.7500 0.086(7) Uani 1 2 d S . .
O6 O 0.3199(9) -0.1605(9) 0.5330(13) 0.090(4) Uani 1 1 d D . .
O7 O 0.4183(6) -0.0154(6) 0.7659(6) 0.036(2) Uani 1 1 d . . .
O8 O 0.2850(6) 0.0127(8) 0.5684(7) 0.050(3) Uani 1 1 d . . .
Sm1 Sm 0.42709(5) -0.04280(4) 0.59258(5) 0.0271(3) Uani 1 1 d . . .
N3 N 0.203(3) -0.229(3) 0.398(4) 0.259(18) Uani 1 1 d DU . .
C17 C 0.240(2) -0.181(5) 0.507(5) 0.40(5) Uani 1 1 d DU . .


_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
C1 C2 1.364(19) . ?
C1 C5 1.409(18) . ?
C1 N2 1.435(15) . ?
C2 C7 1.420(16) . ?
C2 H2 0.9300 . ?
C3 O8 1.300(15) . ?
C3 C4 1.39(2) . ?
C3 C7 1.433(18) . ?
C4 C5 1.358(19) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 C14 1.37(2) . ?
C6 C9 1.41(2) . ?
C6 C11 1.537(18) . ?
C7 C10 1.440(18) . ?
C8 C9 1.35(2) . ?
C8 C12 1.38(2) . ?
C8 N1 1.44(2) . ?
C9 H9 0.9300 . ?
C10 O7 1.265(14) . ?
C10 O3 1.271(14) . ?
C11 O1 1.220(16) . ?
C11 O4 1.257(15) . ?
C12 C13 1.37(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.39(2) . ?
C13 H13 0.9300 . ?
C14 O2 1.33(2) . ?
C15 O5 0.96(6) . ?
C15 N4 1.46(7) . ?
C16 N4 1.49(5) . ?
N1 N1 1.24(2) 3_666 ?
N2 N2 1.26(2) 2_556 ?
N4 C16 1.49(5) 2_656 ?
O1 Sm1 2.423(9) . ?
O3 Sm1 2.334(8) 4_556 ?
O4 Sm1 2.386(9) 3_656 ?
O5 Sm1 2.661(12) 2_656 ?
O5 Sm1 2.661(12) . ?
O6 C17 1.200(10) . ?
O6 Sm1 2.428(13) . ?
O7 Sm1 2.403(7) . ?
O7 Sm1 2.455(9) 2_656 ?
O8 Sm1 2.283(9) . ?
Sm1 O3 2.334(8) 4 ?
Sm1 O4 2.386(9) 3_656 ?
Sm1 O7 2.455(9) 2_656 ?
Sm1 Sm1 3.9243(12) 2_656 ?
N3 C17 1.552(10) . ?

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
C2 C1 C5 119.1(11) . . ?
C2 C1 N2 117.3(11) . . ?
C5 C1 N2 123.4(12) . . ?
C1 C2 C7 122.3(12) . . ?
C1 C2 H2 118.9 . . ?
C7 C2 H2 118.9 . . ?
O8 C3 C4 119.2(11) . . ?
O8 C3 C7 122.4(12) . . ?
C4 C3 C7 118.4(12) . . ?
C5 C4 C3 122.6(12) . . ?
C5 C4 H4 118.7 . . ?
C3 C4 H4 118.7 . . ?
C4 C5 C1 120.0(13) . . ?
C4 C5 H5 120.0 . . ?
C1 C5 H5 120.0 . . ?
C14 C6 C9 118.5(13) . . ?
C14 C6 C11 122.6(13) . . ?
C9 C6 C11 118.9(12) . . ?
C2 C7 C3 117.5(12) . . ?
C2 C7 C10 119.0(11) . . ?
C3 C7 C10 123.5(11) . . ?
C9 C8 C12 118.0(16) . . ?
C9 C8 N1 117.0(14) . . ?
C12 C8 N1 125.0(15) . . ?
C8 C9 C6 121.8(14) . . ?
C8 C9 H9 119.1 . . ?
C6 C9 H9 119.1 . . ?
O7 C10 O3 118.5(11) . . ?
O7 C10 C7 120.7(10) . . ?
O3 C10 C7 120.7(11) . . ?
O1 C11 O4 127.4(13) . . ?
O1 C11 C6 115.1(11) . . ?
O4 C11 C6 117.4(12) . . ?
C13 C12 C8 122.6(17) . . ?
C13 C12 H12 118.7 . . ?
C8 C12 H12 118.7 . . ?
C14 C13 C12 118.4(17) . . ?
C14 C13 H13 120.8 . . ?
C12 C13 H13 120.8 . . ?
O2 C14 C6 121.3(15) . . ?
O2 C14 C13 117.9(15) . . ?
C6 C14 C13 120.6(17) . . ?
O5 C15 N4 180.000(13) . . ?
N1 N1 C8 114.8(19) 3_666 . ?
N2 N2 C1 113.9(14) 2_556 . ?
C15 N4 C16 110(3) . 2_656 ?
C15 N4 C16 110(3) . . ?
C16 N4 C16 139(7) 2_656 . ?
C11 O1 Sm1 137.7(8) . . ?
C10 O3 Sm1 171.3(9) . 4_556 ?
C11 O4 Sm1 140.0(9) . 3_656 ?
C15 O5 Sm1 132.5(3) . 2_656 ?
C15 O5 Sm1 132.5(3) . . ?
Sm1 O5 Sm1 95.0(6) 2_656 . ?
C17 O6 Sm1 144(4) . . ?
C10 O7 Sm1 140.3(8) . . ?
C10 O7 Sm1 111.8(7) . 2_656 ?
Sm1 O7 Sm1 107.8(3) . 2_656 ?
C3 O8 Sm1 140.8(9) . . ?
O8 Sm1 O3 85.0(3) . 4 ?
O8 Sm1 O4 142.6(4) . 3_656 ?
O3 Sm1 O4 75.9(3) 4 3_656 ?
O8 Sm1 O7 69.9(3) . . ?
O3 Sm1 O7 150.9(3) 4 . ?
O4 Sm1 O7 133.1(3) 3_656 . ?
O8 Sm1 O6 75.3(5) . . ?
O3 Sm1 O6 87.3(5) 4 . ?
O4 Sm1 O6 72.0(4) 3_656 . ?
O7 Sm1 O6 99.7(4) . . ?
O8 Sm1 O1 73.7(4) . . ?
O3 Sm1 O1 77.2(3) 4 . ?
O4 Sm1 O1 130.5(3) 3_656 . ?
O7 Sm1 O1 81.7(3) . . ?
O6 Sm1 O1 146.3(4) . . ?
O8 Sm1 O7 130.3(3) . 2_656 ?
O3 Sm1 O7 123.6(3) 4 2_656 ?
O4 Sm1 O7 86.7(3) 3_656 2_656 ?
O7 Sm1 O7 68.3(3) . 2_656 ?
O6 Sm1 O7 137.2(4) . 2_656 ?
O1 Sm1 O7 74.9(3) . 2_656 ?
O8 Sm1 O5 117.9(2) . . ?
O3 Sm1 O5 146.6(3) 4 . ?
O4 Sm1 O5 71.3(3) 3_656 . ?
O7 Sm1 O5 62.0(3) . . ?
O6 Sm1 O5 76.6(5) . . ?
O1 Sm1 O5 130.5(3) . . ?
O7 Sm1 O5 61.4(3) 2_656 . ?
O8 Sm1 Sm1 106.3(2) . 2_656 ?
O3 Sm1 Sm1 158.4(2) 4 2_656 ?
O4 Sm1 Sm1 102.9(2) 3_656 2_656 ?
O7 Sm1 Sm1 36.6(2) . 2_656 ?
O6 Sm1 Sm1 113.0(4) . 2_656 ?
O1 Sm1 Sm1 88.26(19) . 2_656 ?
O7 Sm1 Sm1 35.67(18) 2_656 2_656 ?
O5 Sm1 Sm1 42.5(3) . 2_656 ?
O6 C17 N3 112(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 C1 C2 C7 -1(2) . . . . ?
N2 C1 C2 C7 174.4(13) . . . . ?
O8 C3 C4 C5 175.9(16) . . . . ?
C7 C3 C4 C5 -4(3) . . . . ?
C3 C4 C5 C1 1(3) . . . . ?
C2 C1 C5 C4 1(2) . . . . ?
N2 C1 C5 C4 -173.7(16) . . . . ?
C1 C2 C7 C3 -2(2) . . . . ?
C1 C2 C7 C10 179.9(13) . . . . ?
O8 C3 C7 C2 -175.7(14) . . . . ?
C4 C3 C7 C2 4(2) . . . . ?
O8 C3 C7 C10 2(2) . . . . ?
C4 C3 C7 C10 -177.5(15) . . . . ?
C12 C8 C9 C6 -3(3) . . . . ?
N1 C8 C9 C6 178.3(17) . . . . ?
C14 C6 C9 C8 -1(3) . . . . ?
C11 C6 C9 C8 179.8(17) . . . . ?
C2 C7 C10 O7 170.7(13) . . . . ?
C3 C7 C10 O7 -7(2) . . . . ?
C2 C7 C10 O3 -11(2) . . . . ?
C3 C7 C10 O3 171.1(13) . . . . ?
C14 C6 C11 O1 -8(3) . . . . ?
C9 C6 C11 O1 171.7(15) . . . . ?
C14 C6 C11 O4 171.4(18) . . . . ?
C9 C6 C11 O4 -9(2) . . . . ?
C9 C8 C12 C13 3(4) . . . . ?
N1 C8 C12 C13 -178(2) . . . . ?
C8 C12 C13 C14 0(4) . . . . ?
C9 C6 C14 O2 -179.7(18) . . . . ?
C11 C6 C14 O2 0(3) . . . . ?
C9 C6 C14 C13 4(3) . . . . ?
C11 C6 C14 C13 -176.6(19) . . . . ?
C12 C13 C14 O2 180(2) . . . . ?
C12 C13 C14 C6 -4(4) . . . . ?
C9 C8 N1 N1 177(2) . . . 3_666 ?
C12 C8 N1 N1 -2(4) . . . 3_666 ?
C2 C1 N2 N2 -168.2(10) . . . 2_556 ?
C5 C1 N2 N2 6.8(17) . . . 2_556 ?
O5 C15 N4 C16 12(100) . . . 2_656 ?
O5 C15 N4 C16 -168(100) . . . . ?
O4 C11 O1 Sm1 -10(3) . . . . ?
C6 C11 O1 Sm1 168.8(10) . . . . ?
O7 C10 O3 Sm1 127(5) . . . 4_556 ?
C7 C10 O3 Sm1 -51(6) . . . 4_556 ?
O1 C11 O4 Sm1 -16(3) . . . 3_656 ?
C6 C11 O4 Sm1 164.9(11) . . . 3_656 ?
N4 C15 O5 Sm1 100(100) . . . 2_656 ?
N4 C15 O5 Sm1 -80(100) . . . . ?
O3 C10 O7 Sm1 178.3(9) . . . . ?
C7 C10 O7 Sm1 -3(2) . . . . ?
O3 C10 O7 Sm1 3.4(15) . . . 2_656 ?
C7 C10 O7 Sm1 -178.2(10) . . . 2_656 ?
C4 C3 O8 Sm1 -164.3(13) . . . . ?
C7 C3 O8 Sm1 16(3) . . . . ?
C3 O8 Sm1 O3 177.1(17) . . . 4 ?
C3 O8 Sm1 O4 118.3(15) . . . 3_656 ?
C3 O8 Sm1 O7 -17.8(16) . . . . ?
C3 O8 Sm1 O6 88.6(17) . . . . ?
C3 O8 Sm1 O1 -104.8(17) . . . . ?
C3 O8 Sm1 O7 -52.0(18) . . . 2_656 ?
C3 O8 Sm1 O5 22.8(18) . . . . ?
C3 O8 Sm1 Sm1 -21.6(17) . . . 2_656 ?
C10 O7 Sm1 O8 11.2(13) . . . . ?
Sm1 O7 Sm1 O8 -173.8(5) 2_656 . . . ?
C10 O7 Sm1 O3 43.0(17) . . . 4 ?
Sm1 O7 Sm1 O3 -142.0(5) 2_656 . . 4 ?
C10 O7 Sm1 O4 -133.6(13) . . . 3_656 ?
Sm1 O7 Sm1 O4 41.4(6) 2_656 . . 3_656 ?
C10 O7 Sm1 O6 -59.2(14) . . . . ?
Sm1 O7 Sm1 O6 115.8(5) 2_656 . . . ?
C10 O7 Sm1 O1 86.7(14) . . . . ?
Sm1 O7 Sm1 O1 -98.3(4) 2_656 . . . ?
C10 O7 Sm1 O7 163.7(13) . . . 2_656 ?
Sm1 O7 Sm1 O7 -21.3(5) 2_656 . . 2_656 ?
C10 O7 Sm1 O5 -128.2(14) . . . . ?
Sm1 O7 Sm1 O5 46.8(3) 2_656 . . . ?
C10 O7 Sm1 Sm1 -175.0(16) . . . 2_656 ?
C17 O6 Sm1 O8 -1(6) . . . . ?
C17 O6 Sm1 O3 -87(6) . . . 4 ?
C17 O6 Sm1 O4 -163(6) . . . 3_656 ?
C17 O6 Sm1 O7 65(6) . . . . ?
C17 O6 Sm1 O1 -25(6) . . . . ?
C17 O6 Sm1 O7 133(6) . . . 2_656 ?
C17 O6 Sm1 O5 123(6) . . . . ?
C17 O6 Sm1 Sm1 100(6) . . . 2_656 ?
C11 O1 Sm1 O8 -119.5(14) . . . . ?
C11 O1 Sm1 O3 -31.0(14) . . . 4 ?
C11 O1 Sm1 O4 27.5(15) . . . 3_656 ?
C11 O1 Sm1 O7 169.1(14) . . . . ?
C11 O1 Sm1 O6 -95.8(15) . . . . ?
C11 O1 Sm1 O7 99.4(14) . . . 2_656 ?
C11 O1 Sm1 O5 127.5(13) . . . . ?
C11 O1 Sm1 Sm1 132.9(14) . . . 2_656 ?
C15 O5 Sm1 O8 96.2(4) . . . . ?
Sm1 O5 Sm1 O8 -83.8(4) 2_656 . . . ?
C15 O5 Sm1 O3 -32.3(5) . . . 4 ?
Sm1 O5 Sm1 O3 147.7(5) 2_656 . . 4 ?
C15 O5 Sm1 O4 -44.2(3) . . . 3_656 ?
Sm1 O5 Sm1 O4 135.8(3) 2_656 . . 3_656 ?
C15 O5 Sm1 O7 140.0(3) . . . . ?
Sm1 O5 Sm1 O7 -40.0(3) 2_656 . . . ?
C15 O5 Sm1 O6 31.1(4) . . . . ?
Sm1 O5 Sm1 O6 -148.9(4) 2_656 . . . ?
C15 O5 Sm1 O1 -171.9(3) . . . . ?
Sm1 O5 Sm1 O1 8.1(3) 2_656 . . . ?
C15 O5 Sm1 O7 -140.7(2) . . . 2_656 ?
Sm1 O5 Sm1 O7 39.3(2) 2_656 . . 2_656 ?
C15 O5 Sm1 Sm1 180.000(2) . . . 2_656 ?
Sm1 O6 C17 N3 130(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.903
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.903
_refine_diff_density_max         1.490
_refine_diff_density_min         -2.602
_refine_diff_density_rms         0.390
####################################################################### 
# 
# 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_p2015102406_2_0m
_audit_block_doi                 10.5517/ccdc.csd.cc1nllkd
_database_code_depnum_ccdc_archive 'CCDC 1537214'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C7CC01898C 2017
_audit_update_record             
;
2017-03-10 deposited with the CCDC.
2017-06-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18.50 H17 Eu N3.50 O7.50'
_chemical_formula_weight         560.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'
Eu Eu -0.1578 3.6682 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P1

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

_cell_length_a                   15.516(4)
_cell_length_b                   15.899(5)
_cell_length_c                   13.270(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.469(11)
_cell_angle_gamma                90.00
_cell_volume                     3025.1(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3810
_cell_measurement_theta_min      4.21
_cell_measurement_theta_max      27.43

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1102
_exptl_absorpt_coefficient_mu    2.107
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.8169
_exptl_absorpt_correction_T_max  0.8665
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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            14776
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_av_sigmaI/netI    0.0477
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.56
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4954
_reflns_number_gt                3991
_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)+(0.0810P)²+11.3135P] 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         4954
_refine_ls_number_parameters     246
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0433
_refine_ls_wR_factor_ref         0.1417
_refine_ls_wR_factor_gt          0.1291
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.065
_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
C1 C 0.7675(5) 0.4755(5) 0.3787(5) 0.0271(16) Uani 1 1 d . . .
C2 C 0.9249(5) 0.4475(6) 0.3890(6) 0.042(2) Uani 1 1 d . . .
H2 H 0.9868 0.4349 0.4311 0.051 Uiso 1 1 calc R . .
C3 C 0.5328(5) 0.3364(4) 0.4585(6) 0.0309(17) Uani 1 1 d . . .
C4 C 0.8631(5) 0.4573(6) 0.4378(6) 0.046(2) Uani 1 1 d . . .
H4 H 0.8843 0.4518 0.5132 0.056 Uiso 1 1 calc R . .
C5 C 0.7382(5) 0.4789(4) 0.2624(5) 0.0237(15) Uani 1 1 d . . .
C6 C 0.8965(5) 0.4560(5) 0.2756(6) 0.0352(18) Uani 1 1 d . . .
C7 C 0.8025(5) 0.4691(5) 0.2152(6) 0.0301(17) Uani 1 1 d . . .
H7 H 0.7821 0.4715 0.1396 0.036 Uiso 1 1 calc R . .
C8 C 0.5485(6) 0.2462(4) 0.4341(6) 0.0356(18) Uani 1 1 d . . .
C9 C 0.5159(7) 0.1813(4) 0.4789(7) 0.046(2) Uani 1 1 d . . .
H9 H 0.4828 0.1935 0.5226 0.055 Uiso 1 1 calc R . .
C10 C 0.5957(8) 0.2267(5) 0.3646(9) 0.062(3) Uani 1 1 d . . .
C11 C 0.5319(8) 0.0980(5) 0.4597(8) 0.056(3) Uani 1 1 d . . .
C12 C 0.738(3) 0.6482(17) 0.544(3) 1.21(18) Uiso 1 1 d D . .
H12 H 0.7534 0.5962 0.5786 1.451 Uiso 1 1 calc R . .
C13 C 0.889(2) 0.728(2) 0.600(3) 0.310(19) Uiso 1 1 d D . .
H13A H 0.9194 0.6798 0.6428 0.465 Uiso 1 1 d R . .
H13B H 0.9208 0.7781 0.6349 0.465 Uiso 1 1 d R . .
H13C H 0.8919 0.7234 0.5288 0.465 Uiso 1 1 d R . .
C14 C 0.782(3) 0.753(3) 0.698(3) 0.40(3) Uiso 1 1 d D . .
H14A H 0.7914 0.7027 0.7421 0.607 Uiso 1 1 d R . .
H14B H 0.7222 0.7762 0.6865 0.607 Uiso 1 1 d R . .
H14C H 0.8299 0.7929 0.7358 0.607 Uiso 1 1 d R . .
C15 C 0.5830(10) 0.0818(6) 0.3950(11) 0.092(5) Uani 1 1 d . . .
H15 H 0.5961 0.0266 0.3827 0.110 Uiso 1 1 calc R . .
C16 C 0.6131(11) 0.1443(6) 0.3510(13) 0.097(5) Uani 1 1 d . . .
H16 H 0.6476 0.1315 0.3091 0.116 Uiso 1 1 calc R . .
C17 C 0.5000 0.717(2) 0.2500 0.155(11) Uiso 1 2 d SD . .
C18 C 0.591(3) 0.837(3) 0.284(4) 0.36(3) Uiso 1 1 d . . .
H18A H 0.6072 0.8453 0.2214 0.537 Uiso 1 1 d R . .
H18B H 0.6347 0.7998 0.3343 0.537 Uiso 1 1 d R . .
H18C H 0.5922 0.8906 0.3184 0.537 Uiso 1 1 d R . .
C19 C 0.6408(4) 0.4939(4) 0.1921(5) 0.0202(14) Uani 1 1 d . . .
Eu1 Eu 0.57264(2) 0.542619(19) 0.40634(2) 0.01930(15) Uani 1 1 d . . .
H17 H 0.5576 0.7199 0.2593 0.023 Uiso 1 1 d RD . .
N1 N 0.9572(4) 0.4545(4) 0.2195(5) 0.0385(16) Uani 1 1 d . . .
N2 N 0.4920(8) 0.0376(4) 0.5095(8) 0.066(3) Uani 1 1 d . . .
N3 N 0.7874(18) 0.7309(13) 0.588(2) 0.233(10) Uiso 1 1 d D . .
N4 N 0.5000 0.799(3) 0.2500 0.237(15) Uiso 1 2 d S . .
O1 O 0.7145(3) 0.4871(4) 0.4306(4) 0.0416(14) Uani 1 1 d . . .
O2 O 0.5526(4) 0.3930(3) 0.4043(4) 0.0356(12) Uani 1 1 d . . .
O3 O 0.6132(3) 0.4888(3) 0.0904(3) 0.0267(11) Uani 1 1 d . . .
O4 O 0.5808(3) 0.5136(3) 0.2334(4) 0.0288(11) Uani 1 1 d . . .
O5 O 0.6801(5) 0.6600(4) 0.4650(7) 0.077(2) Uani 1 1 d D . .
O6 O 0.5000 0.6533(5) 0.2500 0.072(3) Uani 1 2 d S . .
O7 O 0.5001(4) 0.3491(3) 0.5299(4) 0.0371(13) Uani 1 1 d . . .
O8 O 0.6299(6) 0.2865(4) 0.3201(7) 0.075(2) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.273(9) . ?
C1 C4 1.418(10) . ?
C1 C5 1.433(9) . ?
C2 C4 1.356(12) . ?
C2 C6 1.403(11) . ?
C2 H2 0.9300 . ?
C3 O7 1.250(9) . ?
C3 O2 1.261(9) . ?
C3 C8 1.511(10) . ?
C4 H4 0.9300 . ?
C5 C7 1.375(11) . ?
C5 C19 1.460(9) . ?
C6 C7 1.386(10) . ?
C6 N1 1.405(11) . ?
C7 H7 0.9300 . ?
C8 C9 1.380(11) . ?
C8 C10 1.414(13) . ?
C9 C11 1.388(11) . ?
C9 H9 0.9300 . ?
C10 O8 1.332(11) . ?
C10 C16 1.363(13) . ?
C11 C15 1.398(15) . ?
C11 N2 1.433(12) . ?
C12 O5 1.106(10) . ?
C12 N3 1.522(10) . ?
C12 H12 0.9300 . ?
C13 N3 1.533(10) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 N3 1.533(10) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.324(16) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 O6 1.01(4) . ?
C17 N4 1.32(4) . ?
C17 H17 0.8567 . ?
C18 N4 1.44(4) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 O3 1.253(8) . ?
C19 O4 1.286(8) . ?
C19 Eu1 3.157(6) 2_655 ?
Eu1 O1 2.277(5) . ?
Eu1 O3 2.332(4) 4_566 ?
Eu1 O7 2.384(5) 3_666 ?
Eu1 O4 2.391(5) . ?
Eu1 O2 2.397(5) . ?
Eu1 O5 2.425(7) . ?
Eu1 O4 2.438(4) 2_655 ?
Eu1 O6 2.624(6) . ?
Eu1 O3 3.023(5) 2_655 ?
Eu1 C19 3.157(6) 2_655 ?
Eu1 Eu1 3.8921(13) 2_655 ?
Eu1 Eu1 4.1690(10) 3_666 ?
N1 N1 1.264(12) 2_755 ?
N2 N2 1.265(13) 3_656 ?
N4 C18 1.44(4) 2_655 ?
O3 Eu1 2.332(4) 4_565 ?
O3 Eu1 3.023(5) 2_655 ?
O4 Eu1 2.438(4) 2_655 ?
O6 Eu1 2.624(6) 2_655 ?
O6 H17 1.3612 . ?
O7 Eu1 2.384(5) 3_666 ?

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 C1 C4 119.0(6) . . ?
O1 C1 C5 124.9(6) . . ?
C4 C1 C5 116.0(6) . . ?
C4 C2 C6 120.8(7) . . ?
C4 C2 H2 119.6 . . ?
C6 C2 H2 119.6 . . ?
O7 C3 O2 125.1(6) . . ?
O7 C3 C8 117.4(7) . . ?
O2 C3 C8 117.5(7) . . ?
C2 C4 C1 122.7(7) . . ?
C2 C4 H4 118.7 . . ?
C1 C4 H4 118.7 . . ?
C7 C5 C1 120.0(6) . . ?
C7 C5 C19 118.7(6) . . ?
C1 C5 C19 121.3(6) . . ?
C7 C6 C2 117.6(7) . . ?
C7 C6 N1 117.8(7) . . ?
C2 C6 N1 124.6(7) . . ?
C5 C7 C6 122.7(7) . . ?
C5 C7 H7 118.6 . . ?
C6 C7 H7 118.6 . . ?
C9 C8 C10 118.9(7) . . ?
C9 C8 C3 120.1(7) . . ?
C10 C8 C3 120.9(7) . . ?
C8 C9 C11 120.9(8) . . ?
C8 C9 H9 119.6 . . ?
C11 C9 H9 119.6 . . ?
O8 C10 C16 119.6(9) . . ?
O8 C10 C8 121.7(7) . . ?
C16 C10 C8 118.4(9) . . ?
C9 C11 C15 118.1(9) . . ?
C9 C11 N2 114.6(9) . . ?
C15 C11 N2 127.2(8) . . ?
O5 C12 N3 109(2) . . ?
O5 C12 H12 125.5 . . ?
N3 C12 H12 125.5 . . ?
N3 C13 H13A 109.4 . . ?
N3 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N3 C13 H13C 109.4 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N3 C14 H14A 109.7 . . ?
N3 C14 H14B 109.3 . . ?
H14A C14 H14B 109.5 . . ?
N3 C14 H14C 109.4 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C11 120.7(9) . . ?
C16 C15 H15 119.6 . . ?
C11 C15 H15 119.6 . . ?
C15 C16 C10 122.8(11) . . ?
C15 C16 H16 118.6 . . ?
C10 C16 H16 118.6 . . ?
O6 C17 N4 180.000(15) . . ?
O6 C17 H17 93.6 . . ?
N4 C17 H17 86.4 . . ?
N4 C18 H18A 109.7 . . ?
N4 C18 H18B 107.6 . . ?
H18A C18 H18B 109.5 . . ?
N4 C18 H18C 111.1 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O3 C19 O4 117.9(6) . . ?
O3 C19 C5 121.5(6) . . ?
O4 C19 C5 120.5(6) . . ?
O3 C19 Eu1 72.3(4) . 2_655 ?
O4 C19 Eu1 45.6(3) . 2_655 ?
C5 C19 Eu1 165.9(5) . 2_655 ?
O1 Eu1 O3 84.81(18) . 4_566 ?
O1 Eu1 O7 142.5(2) . 3_666 ?
O3 Eu1 O7 75.97(17) 4_566 3_666 ?
O1 Eu1 O4 70.02(16) . . ?
O3 Eu1 O4 150.69(17) 4_566 . ?
O7 Eu1 O4 133.31(17) 3_666 . ?
O1 Eu1 O2 74.4(2) . . ?
O3 Eu1 O2 77.35(17) 4_566 . ?
O7 Eu1 O2 130.03(18) 3_666 . ?
O4 Eu1 O2 81.50(17) . . ?
O1 Eu1 O5 75.2(2) . . ?
O3 Eu1 O5 87.2(2) 4_566 . ?
O7 Eu1 O5 72.0(2) 3_666 . ?
O4 Eu1 O5 100.1(2) . . ?
O2 Eu1 O5 146.9(2) . . ?
O1 Eu1 O4 130.11(19) . 2_655 ?
O3 Eu1 O4 123.36(16) 4_566 2_655 ?
O7 Eu1 O4 87.10(18) 3_666 2_655 ?
O4 Eu1 O4 68.2(2) . 2_655 ?
O2 Eu1 O4 73.67(18) . 2_655 ?
O5 Eu1 O4 137.9(2) . 2_655 ?
O1 Eu1 O6 118.17(14) . . ?
O3 Eu1 O6 146.55(17) 4_566 . ?
O7 Eu1 O6 71.20(16) 3_666 . ?
O4 Eu1 O6 62.29(16) . . ?
O2 Eu1 O6 129.93(18) . . ?
O5 Eu1 O6 76.9(2) . . ?
O4 Eu1 O6 61.72(16) 2_655 . ?
O1 Eu1 O3 139.76(19) . 2_655 ?
O3 Eu1 O3 78.53(15) 4_566 2_655 ?
O7 Eu1 O3 67.41(17) 3_666 2_655 ?
O4 Eu1 O3 111.08(14) . 2_655 ?
O2 Eu1 O3 66.35(16) . 2_655 ?
O5 Eu1 O3 139.1(2) . 2_655 ?
O4 Eu1 O3 45.41(15) 2_655 2_655 ?
O6 Eu1 O3 94.44(10) . 2_655 ?
O1 Eu1 C19 140.1(2) . 2_655 ?
O3 Eu1 C19 101.60(17) 4_566 2_655 ?
O7 Eu1 C19 76.11(18) 3_666 2_655 ?
O4 Eu1 C19 89.28(16) . 2_655 ?
O2 Eu1 C19 68.94(18) . 2_655 ?
O5 Eu1 C19 143.7(2) . 2_655 ?
O4 Eu1 C19 22.16(16) 2_655 2_655 ?
O6 Eu1 C19 76.81(14) . 2_655 ?
O3 Eu1 C19 23.26(14) 2_655 2_655 ?
O1 Eu1 Eu1 106.60(12) . 2_655 ?
O3 Eu1 Eu1 158.61(12) 4_566 2_655 ?
O7 Eu1 Eu1 102.62(13) 3_666 2_655 ?
O4 Eu1 Eu1 36.72(11) . 2_655 ?
O2 Eu1 Eu1 88.18(12) . 2_655 ?
O5 Eu1 Eu1 112.9(2) . 2_655 ?
O4 Eu1 Eu1 35.90(12) 2_655 2_655 ?
O6 Eu1 Eu1 42.12(14) . 2_655 ?
O3 Eu1 Eu1 81.28(8) 2_655 2_655 ?
C19 Eu1 Eu1 58.02(12) 2_655 2_655 ?
O1 Eu1 Eu1 120.19(15) . 3_666 ?
O3 Eu1 Eu1 45.29(12) 4_566 3_666 ?
O7 Eu1 Eu1 65.53(12) 3_666 3_666 ?
O4 Eu1 Eu1 138.46(12) . 3_666 ?
O2 Eu1 Eu1 65.58(13) . 3_666 ?
O5 Eu1 Eu1 121.4(2) . 3_666 ?
O4 Eu1 Eu1 78.38(12) 2_655 3_666 ?
O6 Eu1 Eu1 121.52(2) . 3_666 ?
O3 Eu1 Eu1 33.24(8) 2_655 3_666 ?
C19 Eu1 Eu1 56.37(12) 2_655 3_666 ?
Eu1 Eu1 Eu1 114.26(2) 2_655 3_666 ?
N1 N1 C6 114.5(8) 2_755 . ?
N2 N2 C11 113.0(11) 3_656 . ?
C12 N3 C13 111.2(10) . . ?
C12 N3 C14 111.0(10) . . ?
C13 N3 C14 109.9(9) . . ?
C17 N4 C18 115(3) . 2_655 ?
C17 N4 C18 115(3) . . ?
C18 N4 C18 130(5) 2_655 . ?
C1 O1 Eu1 140.3(4) . . ?
C3 O2 Eu1 139.5(5) . . ?
C19 O3 Eu1 170.6(5) . 4_565 ?
C19 O3 Eu1 84.4(4) . 2_655 ?
Eu1 O3 Eu1 101.47(15) 4_565 2_655 ?
C19 O4 Eu1 140.2(4) . . ?
C19 O4 Eu1 112.2(4) . 2_655 ?
Eu1 O4 Eu1 107.38(19) . 2_655 ?
C12 O5 Eu1 112.5(15) . . ?
C17 O6 Eu1 132.12(14) . 2_655 ?
C17 O6 Eu1 132.12(14) . . ?
Eu1 O6 Eu1 95.8(3) 2_655 . ?
C17 O6 H17 38.9 . . ?
Eu1 O6 H17 131.5 2_655 . ?
Eu1 O6 H17 112.4 . . ?
C3 O7 Eu1 140.3(5) . 3_666 ?

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
C6 C2 C4 C1 0.7(14) . . . . ?
O1 C1 C4 C2 -177.3(8) . . . . ?
C5 C1 C4 C2 3.1(13) . . . . ?
O1 C1 C5 C7 177.0(8) . . . . ?
C4 C1 C5 C7 -3.4(11) . . . . ?
O1 C1 C5 C19 -2.0(12) . . . . ?
C4 C1 C5 C19 177.7(7) . . . . ?
C4 C2 C6 C7 -4.2(13) . . . . ?
C4 C2 C6 N1 173.9(8) . . . . ?
C1 C5 C7 C6 0.0(11) . . . . ?
C19 C5 C7 C6 179.0(7) . . . . ?
C2 C6 C7 C5 3.9(12) . . . . ?
N1 C6 C7 C5 -174.4(7) . . . . ?
O7 C3 C8 C9 8.5(11) . . . . ?
O2 C3 C8 C9 -170.6(8) . . . . ?
O7 C3 C8 C10 -172.1(9) . . . . ?
O2 C3 C8 C10 8.8(12) . . . . ?
C10 C8 C9 C11 2.3(14) . . . . ?
C3 C8 C9 C11 -178.2(8) . . . . ?
C9 C8 C10 O8 -179.0(10) . . . . ?
C3 C8 C10 O8 1.6(16) . . . . ?
C9 C8 C10 C16 -4.7(17) . . . . ?
C3 C8 C10 C16 175.9(11) . . . . ?
C8 C9 C11 C15 0.9(16) . . . . ?
C8 C9 C11 N2 -178.6(9) . . . . ?
C9 C11 C15 C16 -2(2) . . . . ?
N2 C11 C15 C16 177.7(14) . . . . ?
C11 C15 C16 C10 -1(2) . . . . ?
O8 C10 C16 C15 178.4(15) . . . . ?
C8 C10 C16 C15 4(2) . . . . ?
C7 C5 C19 O3 8.0(10) . . . . ?
C1 C5 C19 O3 -173.0(7) . . . . ?
C7 C5 C19 O4 -171.3(6) . . . . ?
C1 C5 C19 O4 7.7(10) . . . . ?
C7 C5 C19 Eu1 -161.0(16) . . . 2_655 ?
C1 C5 C19 Eu1 18(2) . . . 2_655 ?
C7 C6 N1 N1 170.3(5) . . . 2_755 ?
C2 C6 N1 N1 -7.8(9) . . . 2_755 ?
C9 C11 N2 N2 -179.9(12) . . . 3_656 ?
C15 C11 N2 N2 1(2) . . . 3_656 ?
O5 C12 N3 C13 -118(4) . . . . ?
O5 C12 N3 C14 120(4) . . . . ?
O6 C17 N4 C18 -18(100) . . . 2_655 ?
O6 C17 N4 C18 162(100) . . . . ?
C4 C1 O1 Eu1 163.0(6) . . . . ?
C5 C1 O1 Eu1 -17.4(13) . . . . ?
O3 Eu1 O1 C1 -176.1(9) 4_566 . . . ?
O7 Eu1 O1 C1 -117.3(8) 3_666 . . . ?
O4 Eu1 O1 C1 19.1(8) . . . . ?
O2 Eu1 O1 C1 105.6(9) . . . . ?
O5 Eu1 O1 C1 -87.6(9) . . . . ?
O4 Eu1 O1 C1 53.7(9) 2_655 . . . ?
O6 Eu1 O1 C1 -21.7(9) . . . . ?
O3 Eu1 O1 C1 118.5(8) 2_655 . . . ?
C19 Eu1 O1 C1 82.0(9) 2_655 . . . ?
Eu1 Eu1 O1 C1 22.3(9) 2_655 . . . ?
Eu1 Eu1 O1 C1 154.4(8) 3_666 . . . ?
O7 C3 O2 Eu1 13.3(12) . . . . ?
C8 C3 O2 Eu1 -167.6(5) . . . . ?
O1 Eu1 O2 C3 116.5(7) . . . . ?
O3 Eu1 O2 C3 28.5(7) 4_566 . . . ?
O7 Eu1 O2 C3 -30.7(8) 3_666 . . . ?
O4 Eu1 O2 C3 -171.9(8) . . . . ?
O5 Eu1 O2 C3 92.7(9) . . . . ?
O4 Eu1 O2 C3 -102.3(7) 2_655 . . . ?
O6 Eu1 O2 C3 -129.5(7) . . . . ?
O3 Eu1 O2 C3 -54.4(7) 2_655 . . . ?
C19 Eu1 O2 C3 -79.4(7) 2_655 . . . ?
Eu1 Eu1 O2 C3 -135.7(7) 2_655 . . . ?
Eu1 Eu1 O2 C3 -17.9(7) 3_666 . . . ?
O4 C19 O3 Eu1 -127(3) . . . 4_565 ?
C5 C19 O3 Eu1 54(3) . . . 4_565 ?
Eu1 C19 O3 Eu1 -129(3) 2_655 . . 4_565 ?
O4 C19 O3 Eu1 2.2(6) . . . 2_655 ?
C5 C19 O3 Eu1 -177.2(6) . . . 2_655 ?
O3 C19 O4 Eu1 -176.1(5) . . . . ?
C5 C19 O4 Eu1 3.3(11) . . . . ?
Eu1 C19 O4 Eu1 -173.2(8) 2_655 . . . ?
O3 C19 O4 Eu1 -2.9(8) . . . 2_655 ?
C5 C19 O4 Eu1 176.5(5) . . . 2_655 ?
O1 Eu1 O4 C19 -11.7(7) . . . . ?
O3 Eu1 O4 C19 -44.1(9) 4_566 . . . ?
O7 Eu1 O4 C19 133.1(7) 3_666 . . . ?
O2 Eu1 O4 C19 -88.1(7) . . . . ?
O5 Eu1 O4 C19 58.4(7) . . . . ?
O4 Eu1 O4 C19 -163.9(6) 2_655 . . . ?
O6 Eu1 O4 C19 127.6(7) . . . . ?
O3 Eu1 O4 C19 -148.6(7) 2_655 . . . ?
C19 Eu1 O4 C19 -156.9(8) 2_655 . . . ?
Eu1 Eu1 O4 C19 173.4(8) 2_655 . . . ?
Eu1 Eu1 O4 C19 -125.1(6) 3_666 . . . ?
O1 Eu1 O4 Eu1 174.9(3) . . . 2_655 ?
O3 Eu1 O4 Eu1 142.5(3) 4_566 . . 2_655 ?
O7 Eu1 O4 Eu1 -40.4(3) 3_666 . . 2_655 ?
O2 Eu1 O4 Eu1 98.4(2) . . . 2_655 ?
O5 Eu1 O4 Eu1 -115.1(3) . . . 2_655 ?
O4 Eu1 O4 Eu1 22.7(2) 2_655 . . 2_655 ?
O6 Eu1 O4 Eu1 -45.81(16) . . . 2_655 ?
O3 Eu1 O4 Eu1 37.9(2) 2_655 . . 2_655 ?
C19 Eu1 O4 Eu1 29.6(2) 2_655 . . 2_655 ?
Eu1 Eu1 O4 Eu1 61.5(3) 3_666 . . 2_655 ?
N3 C12 O5 Eu1 -166.1(15) . . . . ?
O1 Eu1 O5 C12 -57(3) . . . . ?
O3 Eu1 O5 C12 29(3) 4_566 . . . ?
O7 Eu1 O5 C12 105(3) 3_666 . . . ?
O4 Eu1 O5 C12 -123(3) . . . . ?
O2 Eu1 O5 C12 -33(3) . . . . ?
O4 Eu1 O5 C12 169(3) 2_655 . . . ?
O6 Eu1 O5 C12 179(3) . . . . ?
O3 Eu1 O5 C12 97(3) 2_655 . . . ?
C19 Eu1 O5 C12 134(3) 2_655 . . . ?
Eu1 Eu1 O5 C12 -159(3) 2_655 . . . ?
Eu1 Eu1 O5 C12 60(3) 3_666 . . . ?
N4 C17 O6 Eu1 80(100) . . . 2_655 ?
N4 C17 O6 Eu1 -100(100) . . . . ?
O1 Eu1 O6 C17 -96.26(19) . . . . ?
O3 Eu1 O6 C17 32.4(2) 4_566 . . . ?
O7 Eu1 O6 C17 43.90(15) 3_666 . . . ?
O4 Eu1 O6 C17 -140.27(14) . . . . ?
O2 Eu1 O6 C17 170.84(17) . . . . ?
O5 Eu1 O6 C17 -31.3(2) . . . . ?
O4 Eu1 O6 C17 140.94(14) 2_655 . . . ?
O3 Eu1 O6 C17 108.22(9) 2_655 . . . ?
C19 Eu1 O6 C17 123.50(12) 2_655 . . . ?
Eu1 Eu1 O6 C17 180.000(10) 2_655 . . . ?
Eu1 Eu1 O6 C17 87.68(9) 3_666 . . . ?
O1 Eu1 O6 Eu1 83.74(19) . . . 2_655 ?
O3 Eu1 O6 Eu1 -147.6(2) 4_566 . . 2_655 ?
O7 Eu1 O6 Eu1 -136.10(15) 3_666 . . 2_655 ?
O4 Eu1 O6 Eu1 39.73(14) . . . 2_655 ?
O2 Eu1 O6 Eu1 -9.16(17) . . . 2_655 ?
O5 Eu1 O6 Eu1 148.7(2) . . . 2_655 ?
O4 Eu1 O6 Eu1 -39.06(14) 2_655 . . 2_655 ?
O3 Eu1 O6 Eu1 -71.78(9) 2_655 . . 2_655 ?
C19 Eu1 O6 Eu1 -56.50(13) 2_655 . . 2_655 ?
Eu1 Eu1 O6 Eu1 -92.32(8) 3_666 . . 2_655 ?
O2 C3 O7 Eu1 15.3(13) . . . 3_666 ?
C8 C3 O7 Eu1 -163.7(6) . . . 3_666 ?

_diffrn_measured_fraction_theta_max 0.928
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.928
_refine_diff_density_max         1.629
_refine_diff_density_min         -0.794
_refine_diff_density_rms         0.173
####################################################################### 
# 
# 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_p2015110909_0m
_audit_block_doi                 10.5517/ccdc.csd.cc1nllc6
_database_code_depnum_ccdc_archive 'CCDC 1537208'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C7CC01898C 2017
_audit_update_record             
;
2017-03-10 deposited with the CCDC.
2017-06-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H20 N6 O18 Pr2'
_chemical_formula_weight         1070.37

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'
Pr Pr -0.2180 2.8214 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   20.0308(9)
_cell_length_b                   7.3601(3)
_cell_length_c                   25.6802(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.047(2)
_cell_angle_gamma                90.00
_cell_volume                     3656.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8248
_cell_measurement_theta_min      3.52
_cell_measurement_theta_max      27.66

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.945
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2088
_exptl_absorpt_coefficient_mu    2.724
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.7724
_exptl_absorpt_correction_T_max  0.8116
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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            12066
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_sigmaI/netI    0.0223
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.64
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3219
_reflns_number_gt                2944
_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)+(0.0341P)²+24.9120P] 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         3219
_refine_ls_number_parameters     279
_refine_ls_number_restraints     35
_refine_ls_R_factor_all          0.0300
_refine_ls_R_factor_gt           0.0271
_refine_ls_wR_factor_ref         0.0723
_refine_ls_wR_factor_gt          0.0701
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.097
_refine_ls_shift/su_max          0.040
_refine_ls_shift/su_mean         0.002

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
C1 C 0.2836(2) 0.7030(6) 0.14994(16) 0.0285(10) Uani 1 1 d . . .
C2 C 0.2984(3) 0.6624(6) 0.09731(17) 0.0313(10) Uani 1 1 d . . .
C3 C 0.3326(3) 0.7898(7) 0.07234(19) 0.0386(11) Uani 1 1 d . . .
C4 C 0.3477(3) 0.7491(8) 0.0240(2) 0.0469(13) Uani 1 1 d . . .
H4 H 0.3719 0.8315 0.0083 0.056 Uiso 1 1 calc R . .
C5 C 0.3263(3) 0.5855(8) -0.0008(2) 0.0480(14) Uani 1 1 d . . .
H5 H 0.3360 0.5587 -0.0334 0.058 Uiso 1 1 calc R . .
C6 C 0.2908(3) 0.4604(6) 0.0218(2) 0.0392(12) Uani 1 1 d . . .
C7 C 0.2777(3) 0.4982(6) 0.07108(18) 0.0346(11) Uani 1 1 d . . .
H7 H 0.2548 0.4129 0.0868 0.041 Uiso 1 1 calc R . .
C8 C 0.1415(2) 0.8567(5) 0.18247(16) 0.0238(9) Uani 1 1 d . . .
C9 C 0.1219(2) 1.0114(5) 0.14502(16) 0.0217(8) Uani 1 1 d . . .
C10 C 0.0741(2) 0.9760(6) 0.09604(16) 0.0261(9) Uani 1 1 d . . .
H10 H 0.0564 0.8591 0.0890 0.031 Uiso 1 1 calc R . .
C11 C 0.0522(2) 1.1099(6) 0.05768(16) 0.0289(9) Uani 1 1 d . . .
C12 C 0.0777(3) 1.2858(6) 0.06974(17) 0.0359(11) Uani 1 1 d . . .
H12 H 0.0623 1.3788 0.0450 0.043 Uiso 1 1 calc R . .
C13 C 0.1253(3) 1.3233(6) 0.11756(17) 0.0329(11) Uani 1 1 d . . .
H13 H 0.1415 1.4417 0.1242 0.040 Uiso 1 1 calc R . .
C14 C 0.1503(2) 1.1898(5) 0.15675(16) 0.0242(9) Uani 1 1 d . . .
C15 C 0.0544(16) 0.297(2) 0.2248(8) 0.361(18) Uani 1 1 d DU . .
H15 H 0.0474 0.2792 0.1880 0.433 Uiso 1 1 calc R . .
C16 C 0.0296(12) 0.158(3) 0.3246(5) 0.240(9) Uani 1 1 d DU . .
C17 C 0.0000 -0.061(2) 0.2500 0.66(6) Uani 1 2 d SDU . .
H1M H 0.336(4) 0.974(11) 0.121(2) 0.10(3) Uiso 1 1 d D . .
H1W H 0.180(3) 0.830(6) 0.328(3) 0.10(3) Uiso 1 1 d D . .
H2W H 0.124(2) 0.752(10) 0.327(3) 0.11(3) Uiso 1 1 d D . .
N1 N 0.2695(3) 0.2989(6) -0.00867(16) 0.0436(11) Uani 1 1 d . . .
N2 N 0.0071(2) 1.0817(5) 0.00568(14) 0.0327(9) Uani 1 1 d . . .
N3 N 0.0273(13) 0.143(2) 0.2609(7) 0.326(12) Uani 1 1 d DU . .
O1 O 0.26199(17) 0.5773(4) 0.17455(11) 0.0309(7) Uani 1 1 d . . .
O2 O 0.11034(17) 0.7074(4) 0.17340(13) 0.0358(8) Uani 1 1 d . . .
O3 O 0.1602(3) 0.7307(5) 0.31684(18) 0.0554(11) Uani 1 1 d D . .
O4 O 0.2943(2) 0.8635(4) 0.16786(13) 0.0427(9) Uani 1 1 d . . .
O5 O 0.0833(3) 0.4340(11) 0.2457(2) 0.108(3) Uani 1 1 d D . .
O6 O 0.19162(15) 0.8706(4) 0.22450(11) 0.0258(6) Uani 1 1 d . . .
O7 O 0.3522(2) 0.9552(5) 0.09429(16) 0.0506(10) Uani 1 1 d D . .
O8 O 0.19753(16) 1.2325(4) 0.20200(11) 0.0272(7) Uani 1 1 d . . .
O9 O 0.0306(3) 0.6370(9) 0.3405(2) 0.0889(16) Uani 1 1 d . . .
Pr1 Pr 0.203225(11) 0.53908(3) 0.249104(8) 0.01972(10) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.258(5) . ?
C1 O4 1.266(5) . ?
C1 C2 1.487(6) . ?
C2 C7 1.394(6) . ?
C2 C3 1.410(7) . ?
C3 O7 1.356(6) . ?
C3 C4 1.385(7) . ?
C4 C5 1.377(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.380(8) . ?
C5 H5 0.9300 . ?
C6 C7 1.386(7) . ?
C6 N1 1.426(6) . ?
C7 H7 0.9300 . ?
C8 O2 1.255(5) . ?
C8 O6 1.273(5) . ?
C8 C9 1.476(5) . ?
C8 Pr1 2.970(4) . ?
C9 C10 1.394(5) . ?
C9 C14 1.431(6) . ?
C10 C11 1.382(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.397(6) . ?
C11 N2 1.419(5) . ?
C12 C13 1.373(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.403(6) . ?
C13 H13 0.9300 . ?
C14 O8 1.332(5) . ?
C15 O5 1.216(10) . ?
C15 N3 1.642(9) . ?
C15 H15 0.9300 . ?
C16 N3 1.629(9) . ?
C17 N3 1.596(9) . ?
C17 N3 1.596(9) 2 ?
N1 N1 1.227(9) 7 ?
N2 N2 1.253(7) 5_575 ?
N3 N3 1.09(5) 2 ?
O1 Pr1 2.510(3) . ?
O2 Pr1 2.626(3) . ?
O3 Pr1 2.556(4) . ?
O3 H1W 0.846(11) . ?
O3 H2W 0.845(11) . ?
O4 Pr1 2.483(3) 4 ?
O5 Pr1 2.503(5) . ?
O6 Pr1 2.386(3) 4 ?
O6 Pr1 2.516(3) . ?
O7 H1M 0.850(11) . ?
O8 Pr1 2.502(3) 4 ?
O8 Pr1 2.549(3) 1_565 ?
Pr1 O6 2.386(3) 4_545 ?
Pr1 O4 2.483(3) 4_545 ?
Pr1 O8 2.502(3) 4_545 ?
Pr1 O8 2.549(3) 1_545 ?
Pr1 Pr1 4.1245(2) 4 ?
Pr1 Pr1 4.1245(2) 4_545 ?

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 C1 O4 123.4(4) . . ?
O1 C1 C2 119.0(4) . . ?
O4 C1 C2 117.6(4) . . ?
C7 C2 C3 118.4(4) . . ?
C7 C2 C1 120.6(4) . . ?
C3 C2 C1 121.0(4) . . ?
O7 C3 C4 117.4(4) . . ?
O7 C3 C2 122.0(4) . . ?
C4 C3 C2 120.6(4) . . ?
C5 C4 C3 119.3(5) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C4 C5 C6 121.4(5) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C5 C6 C7 119.4(4) . . ?
C5 C6 N1 116.0(4) . . ?
C7 C6 N1 124.6(5) . . ?
C6 C7 C2 120.8(5) . . ?
C6 C7 H7 119.6 . . ?
C2 C7 H7 119.6 . . ?
O2 C8 O6 118.2(4) . . ?
O2 C8 C9 121.3(3) . . ?
O6 C8 C9 120.5(4) . . ?
O2 C8 Pr1 62.0(2) . . ?
O6 C8 Pr1 57.1(2) . . ?
C9 C8 Pr1 169.3(3) . . ?
C10 C9 C14 120.3(4) . . ?
C10 C9 C8 116.6(4) . . ?
C14 C9 C8 123.1(3) . . ?
C11 C10 C9 121.8(4) . . ?
C11 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
C10 C11 C12 118.2(4) . . ?
C10 C11 N2 125.0(4) . . ?
C12 C11 N2 116.8(4) . . ?
C13 C12 C11 120.9(4) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C12 C13 C14 122.5(4) . . ?
C12 C13 H13 118.8 . . ?
C14 C13 H13 118.8 . . ?
O8 C14 C13 120.1(4) . . ?
O8 C14 C9 123.6(3) . . ?
C13 C14 C9 116.3(3) . . ?
O5 C15 N3 120.9(13) . . ?
O5 C15 H15 119.5 . . ?
N3 C15 H15 119.5 . . ?
N3 C17 N3 40.0(18) . 2 ?
N1 N1 C6 114.7(5) 7 . ?
N2 N2 C11 114.2(4) 5_575 . ?
N3 N3 C17 70.0(9) 2 . ?
N3 N3 C16 106(2) 2 . ?
C17 N3 C16 99.2(7) . . ?
N3 N3 C15 98.3(18) 2 . ?
C17 N3 C15 134.3(9) . . ?
C16 N3 C15 126.2(8) . . ?
C1 O1 Pr1 139.1(3) . . ?
C8 O2 Pr1 93.0(2) . . ?
Pr1 O3 H1W 119(5) . . ?
Pr1 O3 H2W 142(5) . . ?
H1W O3 H2W 95.7(16) . . ?
C1 O4 Pr1 139.6(3) . 4 ?
C15 O5 Pr1 128.0(16) . . ?
C8 O6 Pr1 136.6(3) . 4 ?
C8 O6 Pr1 97.8(2) . . ?
Pr1 O6 Pr1 114.55(11) 4 . ?
C3 O7 H1M 111(6) . . ?
C14 O8 Pr1 126.5(2) . 4 ?
C14 O8 Pr1 123.9(2) . 1_565 ?
Pr1 O8 Pr1 109.50(10) 4 1_565 ?
O6 Pr1 O4 70.48(11) 4_545 4_545 ?
O6 Pr1 O5 128.1(2) 4_545 . ?
O4 Pr1 O5 71.01(16) 4_545 . ?
O6 Pr1 O8 68.00(9) 4_545 4_545 ?
O4 Pr1 O8 91.65(11) 4_545 4_545 ?
O5 Pr1 O8 145.46(18) . 4_545 ?
O6 Pr1 O1 73.79(10) 4_545 . ?
O4 Pr1 O1 143.56(11) 4_545 . ?
O5 Pr1 O1 130.06(15) . . ?
O8 Pr1 O1 81.38(10) 4_545 . ?
O6 Pr1 O6 126.34(7) 4_545 . ?
O4 Pr1 O6 134.47(10) 4_545 . ?
O5 Pr1 O6 105.4(2) . . ?
O8 Pr1 O6 65.40(9) 4_545 . ?
O1 Pr1 O6 74.38(10) . . ?
O6 Pr1 O8 66.56(9) 4_545 1_545 ?
O4 Pr1 O8 86.29(10) 4_545 1_545 ?
O5 Pr1 O8 77.6(2) . 1_545 ?
O8 Pr1 O8 132.37(5) 4_545 1_545 ?
O1 Pr1 O8 73.10(10) . 1_545 ?
O6 Pr1 O8 138.54(9) . 1_545 ?
O6 Pr1 O3 121.46(13) 4_545 . ?
O4 Pr1 O3 68.78(12) 4_545 . ?
O5 Pr1 O3 72.8(2) . . ?
O8 Pr1 O3 73.06(14) 4_545 . ?
O1 Pr1 O3 139.88(12) . . ?
O6 Pr1 O3 67.06(11) . . ?
O8 Pr1 O3 146.10(13) 1_545 . ?
O6 Pr1 O2 149.21(11) 4_545 . ?
O4 Pr1 O2 137.21(12) 4_545 . ?
O5 Pr1 O2 68.34(16) . . ?
O8 Pr1 O2 114.89(9) 4_545 . ?
O1 Pr1 O2 76.41(11) . . ?
O6 Pr1 O2 49.84(9) . . ?
O8 Pr1 O2 97.50(9) 1_545 . ?
O3 Pr1 O2 86.81(13) . . ?
O6 Pr1 C8 141.04(11) 4_545 . ?
O4 Pr1 C8 144.79(11) 4_545 . ?
O5 Pr1 C8 88.33(18) . . ?
O8 Pr1 C8 89.94(10) 4_545 . ?
O1 Pr1 C8 71.33(11) . . ?
O6 Pr1 C8 25.13(10) . . ?
O8 Pr1 C8 117.56(10) 1_545 . ?
O3 Pr1 C8 78.13(12) . . ?
O2 Pr1 C8 24.95(10) . . ?
O6 Pr1 Pr1 95.49(7) 4_545 4 ?
O4 Pr1 Pr1 123.16(9) 4_545 4 ?
O5 Pr1 Pr1 134.8(2) . 4 ?
O8 Pr1 Pr1 35.62(6) 4_545 4 ?
O1 Pr1 Pr1 66.85(7) . 4 ?
O6 Pr1 Pr1 31.75(6) . 4 ?
O8 Pr1 Pr1 139.41(7) 1_545 4 ?
O3 Pr1 Pr1 74.48(10) . 4 ?
O2 Pr1 Pr1 79.62(6) . 4 ?
C8 Pr1 Pr1 54.85(8) . 4 ?
O6 Pr1 Pr1 33.70(7) 4_545 4_545 ?
O4 Pr1 Pr1 67.55(7) 4_545 4_545 ?
O5 Pr1 Pr1 98.8(2) . 4_545 ?
O8 Pr1 Pr1 101.69(6) 4_545 4_545 ?
O1 Pr1 Pr1 78.87(7) . 4_545 ?
O6 Pr1 Pr1 151.66(7) . 4_545 ?
O8 Pr1 Pr1 34.88(6) 1_545 4_545 ?
O3 Pr1 Pr1 135.81(9) . 4_545 ?
O2 Pr1 Pr1 131.43(7) . 4_545 ?
C8 Pr1 Pr1 145.95(8) . 4_545 ?
Pr1 Pr1 Pr1 126.312(11) 4 4_545 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C7 11.0(7) . . . . ?
O4 C1 C2 C7 -169.7(5) . . . . ?
O1 C1 C2 C3 -170.0(5) . . . . ?
O4 C1 C2 C3 9.3(7) . . . . ?
C7 C2 C3 O7 177.6(5) . . . . ?
C1 C2 C3 O7 -1.5(8) . . . . ?
C7 C2 C3 C4 -2.5(8) . . . . ?
C1 C2 C3 C4 178.4(5) . . . . ?
O7 C3 C4 C5 -177.5(5) . . . . ?
C2 C3 C4 C5 2.6(9) . . . . ?
C3 C4 C5 C6 -0.6(9) . . . . ?
C4 C5 C6 C7 -1.5(9) . . . . ?
C4 C5 C6 N1 177.9(5) . . . . ?
C5 C6 C7 C2 1.6(8) . . . . ?
N1 C6 C7 C2 -177.8(5) . . . . ?
C3 C2 C7 C6 0.4(8) . . . . ?
C1 C2 C7 C6 179.4(5) . . . . ?
O2 C8 C9 C10 -8.4(6) . . . . ?
O6 C8 C9 C10 170.2(4) . . . . ?
Pr1 C8 C9 C10 96.5(15) . . . . ?
O2 C8 C9 C14 172.4(4) . . . . ?
O6 C8 C9 C14 -9.0(7) . . . . ?
Pr1 C8 C9 C14 -82.7(16) . . . . ?
C14 C9 C10 C11 -0.4(7) . . . . ?
C8 C9 C10 C11 -179.6(4) . . . . ?
C9 C10 C11 C12 -2.0(7) . . . . ?
C9 C10 C11 N2 175.8(4) . . . . ?
C10 C11 C12 C13 2.5(8) . . . . ?
N2 C11 C12 C13 -175.5(5) . . . . ?
C11 C12 C13 C14 -0.5(8) . . . . ?
C12 C13 C14 O8 178.6(5) . . . . ?
C12 C13 C14 C9 -1.9(7) . . . . ?
C10 C9 C14 O8 -178.2(4) . . . . ?
C8 C9 C14 O8 1.0(7) . . . . ?
C10 C9 C14 C13 2.3(7) . . . . ?
C8 C9 C14 C13 -178.5(4) . . . . ?
C5 C6 N1 N1 -171.0(6) . . . 7 ?
C7 C6 N1 N1 8.4(9) . . . 7 ?
C10 C11 N2 N2 -6.6(8) . . . 5_575 ?
C12 C11 N2 N2 171.3(5) . . . 5_575 ?
N3 C17 N3 C16 104(2) 2 . . . ?
N3 C17 N3 C15 -82(3) 2 . . . ?
O5 C15 N3 N3 122(3) . . . 2 ?
O5 C15 N3 C17 -167.8(19) . . . . ?
O5 C15 N3 C16 5(5) . . . . ?
O4 C1 O1 Pr1 17.6(8) . . . . ?
C2 C1 O1 Pr1 -163.1(3) . . . . ?
O6 C8 O2 Pr1 -10.3(4) . . . . ?
C9 C8 O2 Pr1 168.3(4) . . . . ?
O1 C1 O4 Pr1 7.7(8) . . . 4 ?
C2 C1 O4 Pr1 -171.6(3) . . . 4 ?
N3 C15 O5 Pr1 119(2) . . . . ?
O2 C8 O6 Pr1 150.0(3) . . . 4 ?
C9 C8 O6 Pr1 -28.7(6) . . . 4 ?
Pr1 C8 O6 Pr1 139.1(4) . . . 4 ?
O2 C8 O6 Pr1 10.9(4) . . . . ?
C9 C8 O6 Pr1 -167.8(3) . . . . ?
C13 C14 O8 Pr1 -142.3(4) . . . 4 ?
C9 C14 O8 Pr1 38.2(6) . . . 4 ?
C13 C14 O8 Pr1 34.0(6) . . . 1_565 ?
C9 C14 O8 Pr1 -145.5(3) . . . 1_565 ?
C15 O5 Pr1 O6 -49.7(15) . . . 4_545 ?
C15 O5 Pr1 O4 -93.7(15) . . . 4_545 ?
C15 O5 Pr1 O8 -157.2(14) . . . 4_545 ?
C15 O5 Pr1 O1 51.6(16) . . . . ?
C15 O5 Pr1 O6 134.0(15) . . . . ?
C15 O5 Pr1 O8 -3.4(15) . . . 1_545 ?
C15 O5 Pr1 O3 -166.6(15) . . . . ?
C15 O5 Pr1 O2 100.0(15) . . . . ?
C15 O5 Pr1 C8 115.3(15) . . . . ?
C15 O5 Pr1 Pr1 148.1(15) . . . 4 ?
C15 O5 Pr1 Pr1 -31.2(15) . . . 4_545 ?
C1 O1 Pr1 O6 -123.0(5) . . . 4_545 ?
C1 O1 Pr1 O4 -134.5(4) . . . 4_545 ?
C1 O1 Pr1 O5 110.4(5) . . . . ?
C1 O1 Pr1 O8 -53.5(4) . . . 4_545 ?
C1 O1 Pr1 O6 13.2(4) . . . . ?
C1 O1 Pr1 O8 167.2(5) . . . 1_545 ?
C1 O1 Pr1 O3 -3.1(5) . . . . ?
C1 O1 Pr1 O2 64.8(4) . . . . ?
C1 O1 Pr1 C8 39.4(4) . . . . ?
C1 O1 Pr1 Pr1 -19.5(4) . . . 4 ?
C1 O1 Pr1 Pr1 -157.3(4) . . . 4_545 ?
C8 O6 Pr1 O6 134.8(3) . . . 4_545 ?
Pr1 O6 Pr1 O6 -15.54(9) 4 . . 4_545 ?
C8 O6 Pr1 O4 -127.1(3) . . . 4_545 ?
Pr1 O6 Pr1 O4 82.56(19) 4 . . 4_545 ?
C8 O6 Pr1 O5 -48.8(3) . . . . ?
Pr1 O6 Pr1 O5 160.88(17) 4 . . . ?
C8 O6 Pr1 O8 166.8(3) . . . 4_545 ?
Pr1 O6 Pr1 O8 16.44(11) 4 . . 4_545 ?
C8 O6 Pr1 O1 79.2(3) . . . . ?
Pr1 O6 Pr1 O1 -71.09(13) 4 . . . ?
C8 O6 Pr1 O8 39.8(3) . . . 1_545 ?
Pr1 O6 Pr1 O8 -110.52(15) 4 . . 1_545 ?
C8 O6 Pr1 O3 -112.1(3) . . . . ?
Pr1 O6 Pr1 O3 97.56(17) 4 . . . ?
C8 O6 Pr1 O2 -6.0(2) . . . . ?
Pr1 O6 Pr1 O2 -156.30(19) 4 . . . ?
Pr1 O6 Pr1 C8 -150.3(3) 4 . . . ?
C8 O6 Pr1 Pr1 150.3(3) . . . 4 ?
C8 O6 Pr1 Pr1 99.1(3) . . . 4_545 ?
Pr1 O6 Pr1 Pr1 -51.28(19) 4 . . 4_545 ?
C8 O2 Pr1 O6 -89.7(3) . . . 4_545 ?
C8 O2 Pr1 O4 122.0(3) . . . 4_545 ?
C8 O2 Pr1 O5 141.2(3) . . . . ?
C8 O2 Pr1 O8 -1.3(3) . . . 4_545 ?
C8 O2 Pr1 O1 -74.9(3) . . . . ?
C8 O2 Pr1 O6 6.0(2) . . . . ?
C8 O2 Pr1 O8 -145.4(3) . . . 1_545 ?
C8 O2 Pr1 O3 68.4(3) . . . . ?
C8 O2 Pr1 Pr1 -6.4(3) . . . 4 ?
C8 O2 Pr1 Pr1 -136.3(2) . . . 4_545 ?
O2 C8 Pr1 O6 125.5(3) . . . 4_545 ?
O6 C8 Pr1 O6 -65.4(3) . . . 4_545 ?
C9 C8 Pr1 O6 14.7(16) . . . 4_545 ?
O2 C8 Pr1 O4 -88.4(3) . . . 4_545 ?
O6 C8 Pr1 O4 80.8(3) . . . 4_545 ?
C9 C8 Pr1 O4 160.9(14) . . . 4_545 ?
O2 C8 Pr1 O5 -35.7(3) . . . . ?
O6 C8 Pr1 O5 133.5(3) . . . . ?
C9 C8 Pr1 O5 -146.4(15) . . . . ?
O2 C8 Pr1 O8 178.9(3) . . . 4_545 ?
O6 C8 Pr1 O8 -12.0(3) . . . 4_545 ?
C9 C8 Pr1 O8 68.1(15) . . . 4_545 ?
O2 C8 Pr1 O1 97.9(3) . . . . ?
O6 C8 Pr1 O1 -92.9(3) . . . . ?
C9 C8 Pr1 O1 -12.8(15) . . . . ?
O2 C8 Pr1 O6 -169.1(4) . . . . ?
C9 C8 Pr1 O6 80.1(15) . . . . ?
O2 C8 Pr1 O8 39.4(3) . . . 1_545 ?
O6 C8 Pr1 O8 -151.4(2) . . . 1_545 ?
C9 C8 Pr1 O8 -71.3(15) . . . 1_545 ?
O2 C8 Pr1 O3 -108.5(3) . . . . ?
O6 C8 Pr1 O3 60.7(3) . . . . ?
C9 C8 Pr1 O3 140.8(15) . . . . ?
O6 C8 Pr1 O2 169.1(4) . . . . ?
C9 C8 Pr1 O2 -110.8(16) . . . . ?
O2 C8 Pr1 Pr1 172.3(3) . . . 4 ?
O6 C8 Pr1 Pr1 -18.6(2) . . . 4 ?
C9 C8 Pr1 Pr1 61.5(15) . . . 4 ?
O2 C8 Pr1 Pr1 67.7(3) . . . 4_545 ?
O6 C8 Pr1 Pr1 -123.1(2) . . . 4_545 ?
C9 C8 Pr1 Pr1 -43.0(16) . . . 4_545 ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.442
_refine_diff_density_min         -0.850
_refine_diff_density_rms         0.112
####################################################################### 
# 
# 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_Lu
_audit_block_doi                 10.5517/ccdc.csd.cc1nvq5d
_database_code_depnum_ccdc_archive 'CCDC 1545014'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C7CC01898C 2017
_audit_update_record             
;
2017-04-20 deposited with the CCDC.
2017-06-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H12 Lu2 N4 O16'
_chemical_formula_weight         1010.36

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'
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'
Lu Lu -0.4720 5.8584 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   21.617(3)
_cell_length_b                   8.2378(10)
_cell_length_c                   23.158(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.426(5)
_cell_angle_gamma                90.00
_cell_volume                     4068.2(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9052
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      27.86

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.650
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1912
_exptl_absorpt_coefficient_mu    4.889
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.4413
_exptl_absorpt_correction_T_max  0.4731
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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            10077
_diffrn_reflns_av_R_equivalents  0.0547
_diffrn_reflns_av_sigmaI/netI    0.0548
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.78
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3502
_reflns_number_gt                2825
_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)+(0.1727P)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     SHELXL
_refine_ls_extinction_coef       0.00016(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3502
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0904
_refine_ls_R_factor_gt           0.0825
_refine_ls_wR_factor_ref         0.2492
_refine_ls_wR_factor_gt          0.2319
_refine_ls_goodness_of_fit_ref   1.179
_refine_ls_restrained_S_all      1.179
_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
C1 C 0.1723(5) 0.7851(14) 0.1780(5) 0.048(3) Uani 1 1 d . . .
C2 C 0.0492(5) 0.9924(16) 0.0702(5) 0.047(3) Uani 1 1 d . . .
C3 C 0.0924(5) 0.8830(13) 0.0975(5) 0.048(3) Uani 1 1 d . . .
H3 H 0.0988 0.7863 0.0786 0.058 Uiso 1 1 calc R . .
C4 C 0.2597(5) 0.7031(13) 0.3588(5) 0.047(2) Uani 1 1 d . . .
C5 C 0.2630(7) 0.5028(15) 0.4388(6) 0.053(3) Uani 1 1 d . . .
H5 H 0.2362 0.4389 0.4127 0.064 Uiso 1 1 calc R . .
C6 C 0.3254(7) 0.5391(14) 0.5331(6) 0.058(4) Uani 1 1 d . . .
H6 H 0.3416 0.4982 0.5699 0.070 Uiso 1 1 calc R . .
C7 C 0.1269(5) 0.9132(16) 0.1526(5) 0.046(2) Uani 1 1 d . . .
C8 C 0.2816(5) 0.6522(14) 0.4215(4) 0.046(2) Uani 1 1 d . . .
C9 C 0.2840(7) 0.4469(15) 0.4952(5) 0.056(3) Uani 1 1 d . . .
C10 C 0.0432(7) 1.1403(16) 0.0952(5) 0.068(4) Uani 1 1 d . . .
H10 H 0.0165 1.2186 0.0759 0.081 Uiso 1 1 calc R . .
C11 C 0.3225(6) 0.7514(14) 0.4596(5) 0.052(3) Uani 1 1 d . . .
C12 C 0.3437(7) 0.6939(18) 0.5170(5) 0.066(3) Uani 1 1 d . . .
H12 H 0.3695 0.7583 0.5439 0.080 Uiso 1 1 calc R . .
C13 C 0.0779(5) 1.1718(16) 0.1501(5) 0.060(3) Uani 1 1 d . . .
H13 H 0.0714 1.2691 0.1686 0.072 Uiso 1 1 calc R . .
C14 C 0.1217(5) 1.0637(14) 0.1783(5) 0.044(2) Uani 1 1 d . . .
Lu1 Lu 0.24790(2) 0.53693(6) 0.22855(2) 0.0440(3) Uani 1 1 d . . .
N1 N 0.0181(5) 0.9483(11) 0.0129(5) 0.056(3) Uani 1 1 d . . .
N2 N 0.2646(5) 0.3010(11) 0.5184(4) 0.059(3) Uani 1 1 d . . .
O1 O 0.2379(5) 0.5879(14) 0.3221(3) 0.068(3) Uani 1 1 d . . .
O2 O 0.1546(3) 1.1043(9) 0.2294(3) 0.0442(16) Uani 1 1 d . . .
O3 O 0.1557(4) 0.4207(11) 0.2472(4) 0.058(2) Uani 1 1 d . . .
O4 O 0.2122(4) 0.8093(10) 0.2249(3) 0.0486(18) Uani 1 1 d . . .
O5 O 0.1684(4) 0.6438(10) 0.1553(3) 0.058(2) Uani 1 1 d . . .
O6 O 0.3008(4) 0.6425(13) 0.1543(3) 0.069(3) Uani 1 1 d . . .
O7 O 0.2707(4) 0.8493(9) 0.3450(3) 0.053(2) Uani 1 1 d . . .
O8 O 0.3399(5) 0.8990(13) 0.4459(4) 0.070(2) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O5 1.275(14) . ?
C1 O4 1.285(13) . ?
C1 C7 1.495(16) . ?
C1 Lu1 2.755(12) . ?
C2 C10 1.363(17) . ?
C2 C3 1.376(16) . ?
C2 N1 1.432(14) . ?
C3 C7 1.391(15) . ?
C4 O7 1.277(13) . ?
C4 O1 1.308(14) . ?
C4 C8 1.512(15) . ?
C5 C8 1.374(17) . ?
C5 C9 1.388(19) . ?
C6 C9 1.376(18) . ?
C6 C12 1.403(18) . ?
C7 C14 1.388(16) . ?
C8 C11 1.405(16) . ?
C9 N2 1.408(15) . ?
C10 C13 1.392(16) . ?
C11 O8 1.327(15) . ?
C11 C12 1.414(16) . ?
C13 C14 1.383(16) . ?
C14 O2 1.318(13) . ?
Lu1 O2 2.243(6) 4_545 ?
Lu1 O1 2.253(8) . ?
Lu1 O4 2.263(7) 4_545 ?
Lu1 O7 2.287(7) 4_545 ?
Lu1 O3 2.315(9) . ?
Lu1 O4 2.370(8) . ?
Lu1 O5 2.377(7) . ?
Lu1 O6 2.379(8) . ?
N1 N1 1.242(18) 5_575 ?
N2 N2 1.285(19) 7_556 ?
O2 Lu1 2.243(6) 4 ?
O4 Lu1 2.263(7) 4 ?
O7 Lu1 2.287(7) 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
O5 C1 O4 118.7(11) . . ?
O5 C1 C7 119.1(9) . . ?
O4 C1 C7 121.9(10) . . ?
O5 C1 Lu1 59.5(6) . . ?
O4 C1 Lu1 59.2(6) . . ?
C7 C1 Lu1 175.2(8) . . ?
C10 C2 C3 119.7(10) . . ?
C10 C2 N1 123.9(11) . . ?
C3 C2 N1 116.1(10) . . ?
C2 C3 C7 121.7(11) . . ?
O7 C4 O1 125.8(10) . . ?
O7 C4 C8 117.4(9) . . ?
O1 C4 C8 116.4(9) . . ?
C8 C5 C9 120.4(12) . . ?
C9 C6 C12 120.9(11) . . ?
C14 C7 C3 119.0(11) . . ?
C14 C7 C1 123.7(10) . . ?
C3 C7 C1 117.0(10) . . ?
C5 C8 C11 121.4(10) . . ?
C5 C8 C4 118.0(10) . . ?
C11 C8 C4 120.5(9) . . ?
C6 C9 C5 119.7(11) . . ?
C6 C9 N2 115.5(11) . . ?
C5 C9 N2 124.8(13) . . ?
C2 C10 C13 118.7(12) . . ?
O8 C11 C8 123.8(10) . . ?
O8 C11 C12 118.1(11) . . ?
C8 C11 C12 118.0(10) . . ?
C6 C12 C11 119.4(12) . . ?
C14 C13 C10 122.5(12) . . ?
O2 C14 C13 119.1(10) . . ?
O2 C14 C7 122.8(10) . . ?
C13 C14 C7 118.0(10) . . ?
O2 Lu1 O1 76.5(3) 4_545 . ?
O2 Lu1 O4 74.9(3) 4_545 4_545 ?
O1 Lu1 O4 77.6(4) . 4_545 ?
O2 Lu1 O7 121.9(3) 4_545 4_545 ?
O1 Lu1 O7 144.1(3) . 4_545 ?
O4 Lu1 O7 78.6(3) 4_545 4_545 ?
O2 Lu1 O3 142.9(3) 4_545 . ?
O1 Lu1 O3 71.1(3) . . ?
O4 Lu1 O3 80.8(3) 4_545 . ?
O7 Lu1 O3 78.9(3) 4_545 . ?
O2 Lu1 O4 93.4(3) 4_545 . ?
O1 Lu1 O4 77.1(4) . . ?
O4 Lu1 O4 153.94(11) 4_545 . ?
O7 Lu1 O4 126.6(2) 4_545 . ?
O3 Lu1 O4 96.5(3) . . ?
O2 Lu1 O5 137.4(3) 4_545 . ?
O1 Lu1 O5 116.5(4) . . ?
O4 Lu1 O5 145.3(3) 4_545 . ?
O7 Lu1 O5 72.6(3) 4_545 . ?
O3 Lu1 O5 75.1(3) . . ?
O4 Lu1 O5 55.3(3) . . ?
O2 Lu1 O6 72.2(3) 4_545 . ?
O1 Lu1 O6 139.5(3) . . ?
O4 Lu1 O6 117.2(3) 4_545 . ?
O7 Lu1 O6 75.8(3) 4_545 . ?
O3 Lu1 O6 144.7(3) . . ?
O4 Lu1 O6 79.6(3) . . ?
O5 Lu1 O6 74.1(3) . . ?
O2 Lu1 C1 116.8(3) 4_545 . ?
O1 Lu1 C1 97.3(4) . . ?
O4 Lu1 C1 166.1(3) 4_545 . ?
O7 Lu1 C1 99.5(3) 4_545 . ?
O3 Lu1 C1 85.3(3) . . ?
O4 Lu1 C1 27.8(3) . . ?
O5 Lu1 C1 27.5(3) . . ?
O6 Lu1 C1 75.2(3) . . ?
N1 N1 C2 115.8(12) 5_575 . ?
N2 N2 C9 116.7(12) 7_556 . ?
C4 O1 Lu1 132.7(7) . . ?
C14 O2 Lu1 131.1(7) . 4 ?
C1 O4 Lu1 133.0(8) . 4 ?
C1 O4 Lu1 93.0(7) . . ?
Lu1 O4 Lu1 132.1(3) 4 . ?
C1 O5 Lu1 93.0(6) . . ?
C4 O7 Lu1 143.7(7) . 4 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 C2 C3 C7 6(2) . . . . ?
N1 C2 C3 C7 178.5(11) . . . . ?
C2 C3 C7 C14 -6.2(18) . . . . ?
C2 C3 C7 C1 179.7(11) . . . . ?
O5 C1 C7 C14 171.5(11) . . . . ?
O4 C1 C7 C14 -3.2(18) . . . . ?
Lu1 C1 C7 C14 99(9) . . . . ?
O5 C1 C7 C3 -14.7(17) . . . . ?
O4 C1 C7 C3 170.6(11) . . . . ?
Lu1 C1 C7 C3 -87(9) . . . . ?
C9 C5 C8 C11 1(2) . . . . ?
C9 C5 C8 C4 177.1(12) . . . . ?
O7 C4 C8 C5 171.5(12) . . . . ?
O1 C4 C8 C5 -16.1(16) . . . . ?
O7 C4 C8 C11 -12.0(17) . . . . ?
O1 C4 C8 C11 160.4(12) . . . . ?
C12 C6 C9 C5 4(2) . . . . ?
C12 C6 C9 N2 -174.0(13) . . . . ?
C8 C5 C9 C6 -2(2) . . . . ?
C8 C5 C9 N2 175.7(13) . . . . ?
C3 C2 C10 C13 -5(2) . . . . ?
N1 C2 C10 C13 -177.2(13) . . . . ?
C5 C8 C11 O8 -177.2(12) . . . . ?
C4 C8 C11 O8 6.4(19) . . . . ?
C5 C8 C11 C12 -0.8(19) . . . . ?
C4 C8 C11 C12 -177.1(11) . . . . ?
C9 C6 C12 C11 -4(2) . . . . ?
O8 C11 C12 C6 179.2(13) . . . . ?
C8 C11 C12 C6 3(2) . . . . ?
C2 C10 C13 C14 5(2) . . . . ?
C10 C13 C14 O2 177.5(12) . . . . ?
C10 C13 C14 C7 -6(2) . . . . ?
C3 C7 C14 O2 -177.3(10) . . . . ?
C1 C7 C14 O2 -3.6(18) . . . . ?
C3 C7 C14 C13 6.0(17) . . . . ?
C1 C7 C14 C13 179.7(12) . . . . ?
O5 C1 Lu1 O2 144.7(7) . . . 4_545 ?
O4 C1 Lu1 O2 -35.2(7) . . . 4_545 ?
C7 C1 Lu1 O2 -140(9) . . . 4_545 ?
O5 C1 Lu1 O1 -136.7(7) . . . . ?
O4 C1 Lu1 O1 43.4(7) . . . . ?
C7 C1 Lu1 O1 -62(9) . . . . ?
O5 C1 Lu1 O4 -69.5(15) . . . 4_545 ?
O4 C1 Lu1 O4 110.6(10) . . . 4_545 ?
C7 C1 Lu1 O4 6(10) . . . 4_545 ?
O5 C1 Lu1 O7 11.4(8) . . . 4_545 ?
O4 C1 Lu1 O7 -168.4(6) . . . 4_545 ?
C7 C1 Lu1 O7 86(9) . . . 4_545 ?
O5 C1 Lu1 O3 -66.5(7) . . . . ?
O4 C1 Lu1 O3 113.6(7) . . . . ?
C7 C1 Lu1 O3 9(9) . . . . ?
O5 C1 Lu1 O4 179.9(11) . . . . ?
C7 C1 Lu1 O4 -105(9) . . . . ?
O4 C1 Lu1 O5 -179.9(11) . . . . ?
C7 C1 Lu1 O5 75(9) . . . . ?
O5 C1 Lu1 O6 83.9(7) . . . . ?
O4 C1 Lu1 O6 -96.0(7) . . . . ?
C7 C1 Lu1 O6 159(9) . . . . ?
C10 C2 N1 N1 -3(2) . . . 5_575 ?
C3 C2 N1 N1 -175.8(15) . . . 5_575 ?
C6 C9 N2 N2 -167.6(15) . . . 7_556 ?
C5 C9 N2 N2 14(2) . . . 7_556 ?
O7 C4 O1 Lu1 31(2) . . . . ?
C8 C4 O1 Lu1 -140.4(10) . . . . ?
O2 Lu1 O1 C4 43.7(12) 4_545 . . . ?
O4 Lu1 O1 C4 120.9(13) 4_545 . . . ?
O7 Lu1 O1 C4 170.3(10) 4_545 . . . ?
O3 Lu1 O1 C4 -154.7(13) . . . . ?
O4 Lu1 O1 C4 -53.1(12) . . . . ?
O5 Lu1 O1 C4 -93.0(12) . . . . ?
O6 Lu1 O1 C4 3.4(16) . . . . ?
C1 Lu1 O1 C4 -72.2(12) . . . . ?
C13 C14 O2 Lu1 -149.4(9) . . . 4 ?
C7 C14 O2 Lu1 33.9(16) . . . 4 ?
O5 C1 O4 Lu1 165.2(8) . . . 4 ?
C7 C1 O4 Lu1 -20.2(16) . . . 4 ?
Lu1 C1 O4 Lu1 165.3(10) . . . 4 ?
O5 C1 O4 Lu1 -0.1(11) . . . . ?
C7 C1 O4 Lu1 174.5(10) . . . . ?
O2 Lu1 O4 C1 149.0(7) 4_545 . . . ?
O1 Lu1 O4 C1 -135.6(7) . . . . ?
O4 Lu1 O4 C1 -149.2(7) 4_545 . . . ?
O7 Lu1 O4 C1 14.2(8) 4_545 . . . ?
O3 Lu1 O4 C1 -66.8(7) . . . . ?
O5 Lu1 O4 C1 0.1(6) . . . . ?
O6 Lu1 O4 C1 77.8(7) . . . . ?
O2 Lu1 O4 Lu1 -16.5(5) 4_545 . . 4 ?
O1 Lu1 O4 Lu1 58.8(5) . . . 4 ?
O4 Lu1 O4 Lu1 45.3(5) 4_545 . . 4 ?
O7 Lu1 O4 Lu1 -151.3(5) 4_545 . . 4 ?
O3 Lu1 O4 Lu1 127.7(5) . . . 4 ?
O5 Lu1 O4 Lu1 -165.5(7) . . . 4 ?
O6 Lu1 O4 Lu1 -87.8(5) . . . 4 ?
C1 Lu1 O4 Lu1 -165.5(10) . . . 4 ?
O4 C1 O5 Lu1 0.1(11) . . . . ?
C7 C1 O5 Lu1 -174.7(9) . . . . ?
O2 Lu1 O5 C1 -49.7(9) 4_545 . . . ?
O1 Lu1 O5 C1 49.4(8) . . . . ?
O4 Lu1 O5 C1 156.7(7) 4_545 . . . ?
O7 Lu1 O5 C1 -168.2(8) 4_545 . . . ?
O3 Lu1 O5 C1 109.0(7) . . . . ?
O4 Lu1 O5 C1 -0.1(6) . . . . ?
O6 Lu1 O5 C1 -88.4(7) . . . . ?
O1 C4 O7 Lu1 15(2) . . . 4 ?
C8 C4 O7 Lu1 -173.3(9) . . . 4 ?

_diffrn_measured_fraction_theta_max 0.976
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.976
_refine_diff_density_max         5.614
_refine_diff_density_min         -3.942
_refine_diff_density_rms         0.332

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 -0.323 0.215 725 264 ' '
2 0.500 -0.028 0.099 725 264 ' '
_platon_squeeze_details          
;
;
####################################################################### 
# 
# 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_p2015110917_0m
_audit_block_doi                 10.5517/ccdc.csd.cc1nllrl
_database_code_depnum_ccdc_archive 'CCDC 1537220'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C7CC01898C 2017
_audit_update_record             
;
2017-03-10 deposited with the CCDC.
2017-06-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H18 Dy N3 O9'
_chemical_formula_weight         570.84

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Dy Dy -0.1892 4.4098 '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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.7525(13)
_cell_length_b                   8.7492(12)
_cell_length_c                   27.498(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.074(9)
_cell_angle_gamma                90.00
_cell_volume                     2059.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7654
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      27.68

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.841
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1116
_exptl_absorpt_coefficient_mu    3.683
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.5263
_exptl_absorpt_correction_T_max  0.5903
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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            13190
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_sigmaI/netI    0.0255
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.38
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3633
_reflns_number_gt                3251
_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)+(0.0241P)²+1.0336P] 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         3633
_refine_ls_number_parameters     293
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0223
_refine_ls_R_factor_gt           0.0187
_refine_ls_wR_factor_ref         0.0472
_refine_ls_wR_factor_gt          0.0461
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.059
_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
C1 C 0.6947(4) 0.1527(4) 0.14662(13) 0.0354(8) Uani 1 1 d . . .
H1 H 0.6032 0.1842 0.1253 0.042 Uiso 1 1 calc R . .
C2 C 0.8152(6) 0.1618(6) 0.07574(15) 0.0703(13) Uani 1 1 d . . .
H2A H 0.7135 0.1966 0.0592 0.105 Uiso 1 1 calc R . .
H2B H 0.8405 0.0697 0.0602 0.105 Uiso 1 1 calc R . .
H2C H 0.8913 0.2390 0.0734 0.105 Uiso 1 1 calc R . .
C3 C 0.9573(7) 0.0785(10) 0.1579(3) 0.135(3) Uani 1 1 d . . .
H3A H 0.9982 0.1550 0.1821 0.202 Uiso 1 1 calc R . .
H3B H 1.0320 0.0581 0.1376 0.202 Uiso 1 1 calc R . .
H3C H 0.9372 -0.0136 0.1745 0.202 Uiso 1 1 calc R . .
C4 C 0.6556(3) -0.1859(3) 0.32457(9) 0.0201(6) Uani 1 1 d . . .
C5 C 0.7415(3) -0.0638(3) 0.35588(10) 0.0194(6) Uani 1 1 d . . .
C6 C 0.7625(4) 0.0849(3) 0.33803(11) 0.0228(6) Uani 1 1 d . . .
C7 C 0.8444(4) 0.1912(4) 0.37230(11) 0.0374(8) Uani 1 1 d . . .
H7 H 0.8554 0.2908 0.3617 0.045 Uiso 1 1 calc R . .
C8 C 0.9080(4) 0.1541(4) 0.42025(12) 0.0399(9) Uani 1 1 d . . .
H8 H 0.9612 0.2278 0.4417 0.048 Uiso 1 1 calc R . .
C9 C 0.8937(4) 0.0044(3) 0.43770(10) 0.0258(6) Uani 1 1 d . . .
C10 C 0.8096(3) -0.1002(3) 0.40528(10) 0.0231(6) Uani 1 1 d . . .
H10 H 0.7975 -0.1987 0.4166 0.028 Uiso 1 1 calc R . .
C11 C 0.4398(4) 0.2499(3) 0.33421(10) 0.0238(6) Uani 1 1 d . . .
C12 C 0.4158(4) 0.2283(3) 0.38579(11) 0.0268(7) Uani 1 1 d . . .
C13 C 0.3437(5) 0.0961(4) 0.39927(13) 0.0398(9) Uani 1 1 d . . .
C14 C 0.3225(6) 0.0810(4) 0.44755(15) 0.0585(12) Uani 1 1 d . . .
H14 H 0.2765 -0.0072 0.4568 0.070 Uiso 1 1 calc R . .
C15 C 0.3683(5) 0.1938(5) 0.48160(12) 0.0513(10) Uani 1 1 d . . .
H15 H 0.3535 0.1817 0.5139 0.062 Uiso 1 1 calc R . .
C16 C 0.4367(4) 0.3262(4) 0.46868(11) 0.0344(7) Uani 1 1 d . . .
C17 C 0.4631(4) 0.3409(3) 0.42094(10) 0.0283(7) Uani 1 1 d . . .
H17 H 0.5132 0.4276 0.4125 0.034 Uiso 1 1 calc R . .
Dy1 Dy 0.496684(15) 0.063717(13) 0.233494(4) 0.01682(6) Uani 1 1 d . . .
H1M H 0.324(5) 0.000(5) 0.3399(10) 0.069(14) Uiso 1 1 d D . .
H1W H 1.027(4) 0.076(2) 0.2674(13) 0.014(9) Uiso 1 1 d D . .
H2W H 0.9156(16) -0.012(8) 0.270(5) 0.28(6) Uiso 1 1 d D . .
H3W H 0.187(3) -0.057(3) 0.2454(13) 0.049(12) Uiso 1 1 d D . .
H4W H 0.244(4) -0.1613(15) 0.2231(12) 0.045(11) Uiso 1 1 d D . .
N1 N 0.8156(4) 0.1321(4) 0.12728(11) 0.0455(8) Uani 1 1 d . . .
N2 N 0.9622(3) -0.0492(3) 0.48572(9) 0.0287(6) Uani 1 1 d . . .
N3 N 0.4760(4) 0.4384(3) 0.50688(10) 0.0393(7) Uani 1 1 d . . .
O1 O 0.5713(2) -0.1570(2) 0.28149(7) 0.0233(4) Uani 1 1 d . . .
O2 O 0.3982(3) 0.1412(2) 0.30323(7) 0.0287(5) Uani 1 1 d . . .
O3 O 0.2579(3) -0.0682(2) 0.22962(8) 0.0280(5) Uani 1 1 d D . .
O4 O 0.7139(2) 0.1262(2) 0.29112(7) 0.0249(4) Uani 1 1 d . . .
O5 O 0.4989(3) 0.3721(2) 0.32380(7) 0.0298(5) Uani 1 1 d . . .
O6 O 0.6891(3) 0.1347(3) 0.19048(8) 0.0404(6) Uani 1 1 d . . .
O7 O 0.6627(2) -0.3214(2) 0.33975(7) 0.0293(5) Uani 1 1 d . . .
O8 O 0.2945(4) -0.0176(3) 0.36667(10) 0.0604(9) Uani 1 1 d D . .
O9 O 1.0146(7) -0.0184(12) 0.2785(2) 0.164(3) Uani 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
C1 O6 1.227(4) . ?
C1 N1 1.293(4) . ?
C1 H1 0.9300 . ?
C2 N1 1.440(5) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 N1 1.424(6) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 O7 1.254(3) . ?
C4 O1 1.283(3) . ?
C4 C5 1.476(4) . ?
C4 Dy1 2.870(3) 2_645 ?
C5 C10 1.401(4) . ?
C5 C6 1.416(4) . ?
C6 O4 1.321(3) . ?
C6 C7 1.409(4) . ?
C7 C8 1.359(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.409(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.379(4) . ?
C9 N2 1.411(4) . ?
C10 H10 0.9300 . ?
C11 O5 1.247(3) . ?
C11 O2 1.278(3) . ?
C11 C12 1.488(4) . ?
C12 C17 1.381(4) . ?
C12 C13 1.405(4) . ?
C13 O8 1.348(4) . ?
C13 C14 1.385(5) . ?
C14 C15 1.362(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.384(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.386(4) . ?
C16 N3 1.426(4) . ?
C17 H17 0.9300 . ?
Dy1 O4 2.2729(19) . ?
Dy1 O5 2.3061(19) 2_645 ?
Dy1 O6 2.336(2) . ?
Dy1 O1 2.3530(18) . ?
Dy1 O2 2.3602(19) . ?
Dy1 O3 2.371(2) . ?
Dy1 O7 2.4158(19) 2_655 ?
Dy1 O1 2.5281(18) 2_655 ?
Dy1 C4 2.870(3) 2_655 ?
N2 N2 1.256(5) 3_756 ?
N3 N3 1.244(5) 3_666 ?
O1 Dy1 2.5281(18) 2_645 ?
O3 H3W 0.836(10) . ?
O3 H4W 0.838(10) . ?
O5 Dy1 2.3061(19) 2_655 ?
O7 Dy1 2.4158(19) 2_645 ?
O8 H1M 0.844(10) . ?
O9 H1W 0.892(10) . ?
O9 H2W 0.851(10) . ?

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
O6 C1 N1 126.2(4) . . ?
O6 C1 H1 116.9 . . ?
N1 C1 H1 116.9 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C3 H3A 109.5 . . ?
N1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
O7 C4 O1 118.2(2) . . ?
O7 C4 C5 120.4(2) . . ?
O1 C4 C5 121.4(2) . . ?
O7 C4 Dy1 56.51(13) . 2_645 ?
O1 C4 Dy1 61.70(14) . 2_645 ?
C5 C4 Dy1 176.4(2) . 2_645 ?
C10 C5 C6 119.0(2) . . ?
C10 C5 C4 117.5(2) . . ?
C6 C5 C4 123.4(2) . . ?
O4 C6 C7 119.1(2) . . ?
O4 C6 C5 123.5(3) . . ?
C7 C6 C5 117.4(3) . . ?
C8 C7 C6 122.6(3) . . ?
C8 C7 H7 118.7 . . ?
C6 C7 H7 118.7 . . ?
C7 C8 C9 120.3(3) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C10 C9 C8 118.0(3) . . ?
C10 C9 N2 116.7(3) . . ?
C8 C9 N2 125.2(3) . . ?
C9 C10 C5 122.5(3) . . ?
C9 C10 H10 118.8 . . ?
C5 C10 H10 118.8 . . ?
O5 C11 O2 124.0(3) . . ?
O5 C11 C12 118.4(3) . . ?
O2 C11 C12 117.6(2) . . ?
C17 C12 C13 119.2(3) . . ?
C17 C12 C11 119.7(3) . . ?
C13 C12 C11 121.1(3) . . ?
O8 C13 C14 118.6(3) . . ?
O8 C13 C12 122.1(3) . . ?
C14 C13 C12 119.3(3) . . ?
C15 C14 C13 120.7(3) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C14 C15 C16 120.7(3) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C15 C16 C17 119.2(3) . . ?
C15 C16 N3 116.0(3) . . ?
C17 C16 N3 124.9(3) . . ?
C12 C17 C16 120.8(3) . . ?
C12 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
O4 Dy1 O5 121.34(8) . 2_645 ?
O4 Dy1 O6 72.68(8) . . ?
O5 Dy1 O6 74.37(8) 2_645 . ?
O4 Dy1 O1 73.32(7) . . ?
O5 Dy1 O1 75.19(7) 2_645 . ?
O6 Dy1 O1 110.95(8) . . ?
O4 Dy1 O2 76.04(7) . . ?
O5 Dy1 O2 145.59(7) 2_645 . ?
O6 Dy1 O2 139.41(8) . . ?
O1 Dy1 O2 83.44(7) . . ?
O4 Dy1 O3 138.57(7) . . ?
O5 Dy1 O3 75.88(8) 2_645 . ?
O6 Dy1 O3 146.02(8) . . ?
O1 Dy1 O3 76.36(7) . . ?
O2 Dy1 O3 73.03(7) . . ?
O4 Dy1 O7 137.23(7) . 2_655 ?
O5 Dy1 O7 79.75(7) 2_645 2_655 ?
O6 Dy1 O7 79.57(8) . 2_655 ?
O1 Dy1 O7 148.54(7) . 2_655 ?
O2 Dy1 O7 108.21(7) . 2_655 ?
O3 Dy1 O7 79.35(7) . 2_655 ?
O4 Dy1 O1 90.86(7) . 2_655 ?
O5 Dy1 O1 128.91(6) 2_645 2_655 ?
O6 Dy1 O1 80.23(8) . 2_655 ?
O1 Dy1 O1 155.90(3) . 2_655 ?
O2 Dy1 O1 75.01(6) . 2_655 ?
O3 Dy1 O1 106.75(7) . 2_655 ?
O7 Dy1 O1 52.19(6) 2_655 2_655 ?
O4 Dy1 C4 115.32(7) . 2_655 ?
O5 Dy1 C4 104.30(7) 2_645 2_655 ?
O6 Dy1 C4 79.35(8) . 2_655 ?
O1 Dy1 C4 168.72(7) . 2_655 ?
O2 Dy1 C4 91.53(7) . 2_655 ?
O3 Dy1 C4 92.54(8) . 2_655 ?
O7 Dy1 C4 25.66(7) 2_655 2_655 ?
O1 Dy1 C4 26.55(7) 2_655 2_655 ?
C1 N1 C3 119.3(4) . . ?
C1 N1 C2 123.1(3) . . ?
C3 N1 C2 117.6(4) . . ?
N2 N2 C9 115.0(3) 3_756 . ?
N3 N3 C16 114.6(3) 3_666 . ?
C4 O1 Dy1 135.88(17) . . ?
C4 O1 Dy1 91.75(16) . 2_645 ?
Dy1 O1 Dy1 132.35(8) . 2_645 ?
C11 O2 Dy1 130.85(18) . . ?
Dy1 O3 H3W 132(2) . . ?
Dy1 O3 H4W 125(2) . . ?
H3W O3 H4W 97.5(14) . . ?
C6 O4 Dy1 131.76(17) . . ?
C11 O5 Dy1 147.9(2) . 2_655 ?
C1 O6 Dy1 135.4(2) . . ?
C4 O7 Dy1 97.83(16) . 2_645 ?
C13 O8 H1M 109(3) . . ?
H1W O9 H2W 91.7(14) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O7 C4 C5 C10 -9.8(4) . . . . ?
O1 C4 C5 C10 169.8(3) . . . . ?
Dy1 C4 C5 C10 -40(3) 2_645 . . . ?
O7 C4 C5 C6 168.0(3) . . . . ?
O1 C4 C5 C6 -12.4(4) . . . . ?
Dy1 C4 C5 C6 138(3) 2_645 . . . ?
C10 C5 C6 O4 174.3(3) . . . . ?
C4 C5 C6 O4 -3.5(5) . . . . ?
C10 C5 C6 C7 -3.4(4) . . . . ?
C4 C5 C6 C7 178.8(3) . . . . ?
O4 C6 C7 C8 -175.0(3) . . . . ?
C5 C6 C7 C8 2.8(5) . . . . ?
C6 C7 C8 C9 0.0(6) . . . . ?
C7 C8 C9 C10 -2.1(5) . . . . ?
C7 C8 C9 N2 176.2(3) . . . . ?
C8 C9 C10 C5 1.4(5) . . . . ?
N2 C9 C10 C5 -177.1(3) . . . . ?
C6 C5 C10 C9 1.4(5) . . . . ?
C4 C5 C10 C9 179.4(3) . . . . ?
O5 C11 C12 C17 -1.8(4) . . . . ?
O2 C11 C12 C17 178.2(3) . . . . ?
O5 C11 C12 C13 177.2(3) . . . . ?
O2 C11 C12 C13 -2.8(5) . . . . ?
C17 C12 C13 O8 179.8(3) . . . . ?
C11 C12 C13 O8 0.7(6) . . . . ?
C17 C12 C13 C14 -0.5(6) . . . . ?
C11 C12 C13 C14 -179.5(4) . . . . ?
O8 C13 C14 C15 -179.1(4) . . . . ?
C12 C13 C14 C15 1.2(7) . . . . ?
C13 C14 C15 C16 0.2(7) . . . . ?
C14 C15 C16 C17 -2.2(6) . . . . ?
C14 C15 C16 N3 178.3(4) . . . . ?
C13 C12 C17 C16 -1.6(5) . . . . ?
C11 C12 C17 C16 177.5(3) . . . . ?
C15 C16 C17 C12 2.9(5) . . . . ?
N3 C16 C17 C12 -177.6(3) . . . . ?
O6 C1 N1 C3 2.3(7) . . . . ?
O6 C1 N1 C2 -177.2(4) . . . . ?
C10 C9 N2 N2 -179.9(3) . . . 3_756 ?
C8 C9 N2 N2 1.7(5) . . . 3_756 ?
C15 C16 N3 N3 -173.8(4) . . . 3_666 ?
C17 C16 N3 N3 6.7(6) . . . 3_666 ?
O7 C4 O1 Dy1 175.98(18) . . . . ?
C5 C4 O1 Dy1 -3.6(4) . . . . ?
Dy1 C4 O1 Dy1 178.4(2) 2_645 . . . ?
O7 C4 O1 Dy1 -2.4(3) . . . 2_645 ?
C5 C4 O1 Dy1 178.0(2) . . . 2_645 ?
O4 Dy1 O1 C4 20.1(2) . . . . ?
O5 Dy1 O1 C4 150.0(3) 2_645 . . . ?
O6 Dy1 O1 C4 83.5(3) . . . . ?
O2 Dy1 O1 C4 -57.2(2) . . . . ?
O3 Dy1 O1 C4 -131.3(3) . . . . ?
O7 Dy1 O1 C4 -171.7(2) 2_655 . . . ?
O1 Dy1 O1 C4 -30.7(2) 2_655 . . . ?
C4 Dy1 O1 C4 -121.2(3) 2_655 . . . ?
O4 Dy1 O1 Dy1 -162.06(13) . . . 2_645 ?
O5 Dy1 O1 Dy1 -32.21(11) 2_645 . . 2_645 ?
O6 Dy1 O1 Dy1 -98.64(12) . . . 2_645 ?
O2 Dy1 O1 Dy1 120.60(12) . . . 2_645 ?
O3 Dy1 O1 Dy1 46.52(11) . . . 2_645 ?
O7 Dy1 O1 Dy1 6.1(2) 2_655 . . 2_645 ?
O1 Dy1 O1 Dy1 147.10(12) 2_655 . . 2_645 ?
C4 Dy1 O1 Dy1 56.6(4) 2_655 . . 2_645 ?
O5 C11 O2 Dy1 29.6(4) . . . . ?
C12 C11 O2 Dy1 -150.4(2) . . . . ?
O4 Dy1 O2 C11 39.5(2) . . . . ?
O5 Dy1 O2 C11 165.3(2) 2_645 . . . ?
O6 Dy1 O2 C11 -0.9(3) . . . . ?
O1 Dy1 O2 C11 113.9(2) . . . . ?
O3 Dy1 O2 C11 -168.4(3) . . . . ?
O7 Dy1 O2 C11 -96.1(2) 2_655 . . . ?
O1 Dy1 O2 C11 -55.2(2) 2_655 . . . ?
C4 Dy1 O2 C11 -76.2(2) 2_655 . . . ?
C7 C6 O4 Dy1 -145.3(2) . . . . ?
C5 C6 O4 Dy1 37.1(4) . . . . ?
O5 Dy1 O4 C6 -96.7(2) 2_645 . . . ?
O6 Dy1 O4 C6 -155.3(3) . . . . ?
O1 Dy1 O4 C6 -36.3(2) . . . . ?
O2 Dy1 O4 C6 50.9(2) . . . . ?
O3 Dy1 O4 C6 8.3(3) . . . . ?
O7 Dy1 O4 C6 152.8(2) 2_655 . . . ?
O1 Dy1 O4 C6 125.2(2) 2_655 . . . ?
C4 Dy1 O4 C6 135.9(2) 2_655 . . . ?
O2 C11 O5 Dy1 38.4(5) . . . 2_655 ?
C12 C11 O5 Dy1 -141.6(3) . . . 2_655 ?
N1 C1 O6 Dy1 -149.9(3) . . . . ?
O4 Dy1 O6 C1 -175.1(3) . . . . ?
O5 Dy1 O6 C1 54.1(3) 2_645 . . . ?
O1 Dy1 O6 C1 121.1(3) . . . . ?
O2 Dy1 O6 C1 -133.9(3) . . . . ?
O3 Dy1 O6 C1 24.4(4) . . . . ?
O7 Dy1 O6 C1 -28.0(3) 2_655 . . . ?
O1 Dy1 O6 C1 -81.1(3) 2_655 . . . ?
C4 Dy1 O6 C1 -54.2(3) 2_655 . . . ?
O1 C4 O7 Dy1 2.5(3) . . . 2_645 ?
C5 C4 O7 Dy1 -177.8(2) . . . 2_645 ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.716
_refine_diff_density_min         -0.486
_refine_diff_density_rms         0.086
