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#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
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#  as required by the journal to which it was submitted.
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data_Compound_1


_audit_creation_method           SHELXL-2013
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C66 H44 Cl6 La2 N4 O14'
_chemical_melting_point          ?

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colorless

_diffrn_ambient_temperature      293(2)
_chemical_formula_weight         1607.57

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'
Cl Cl 0.1484 0.1585 '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'

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

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

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

_cell_length_a                   10.0914(5)
_cell_length_b                   12.6143(6)
_cell_length_c                   13.2987(6)
_cell_angle_alpha                99.312(3)
_cell_angle_beta                 100.740(4)
_cell_angle_gamma                96.354(4)
_cell_volume                     1623.89(14)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    21900
_cell_measurement_theta_min      4.672
_cell_measurement_theta_max      45.288
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.644
_exptl_crystal_F_000             796
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    1.613
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6783
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS, Bruker-AXS (2008)'

_exptl_special_details           
;
 ?
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21899
_diffrn_reflns_av_unetI/netI     0.0554
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.586
_diffrn_reflns_theta_max         27.632
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7553
_reflns_number_gt                6092
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX, Bruker-AXS'
_computing_cell_refinement       'SAINT, Bruker-AXS'
_computing_data_reduction        'SAINT, Bruker-AXS'
_computing_structure_solution    'SIR92 (Gualardi, 1994)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Crystal Maker (Palmer, 2009)'
_computing_publication_material  'WINGX (Farrugia, 2012)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0250P)²+0.0180P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7553
_refine_ls_number_parameters     423
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0347
_refine_ls_wR_factor_ref         0.0659
_refine_ls_wR_factor_gt          0.0603
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
La1 La 0.15010(2) 0.12744(2) 0.99909(2) 0.02853(6) Uani 1 1 d . . . . .
Cl1 Cl -0.64285(10) 0.08804(10) 0.54766(9) 0.0761(3) Uani 1 1 d . . . . .
Cl2 Cl -0.07004(12) -0.27970(11) 0.33720(7) 0.0860(4) Uani 1 1 d . . . . .
Cl3 Cl 0.74914(18) 0.44509(12) 1.58956(11) 0.1352(7) Uani 1 1 d . . . . .
O2 O 0.1319(2) -0.05218(16) 1.05850(16) 0.0419(5) Uani 1 1 d . . . . .
OW1 O 0.3553(2) 0.05028(19) 0.94572(19) 0.0453(6) Uani 1 1 d D . . . .
O3 O 0.0905(2) -0.00415(17) 0.82807(16) 0.0447(6) Uani 1 1 d . . . . .
O1 O -0.0417(2) 0.18919(16) 0.87978(17) 0.0430(5) Uani 1 1 d . . . . .
O4 O 0.0551(2) 0.14335(17) 1.15551(16) 0.0494(6) Uani 1 1 d . . . . .
O5 O 0.3589(2) 0.20397(18) 1.13128(17) 0.0481(6) Uani 1 1 d . . . . .
O6 O 0.5570(2) 0.15571(18) 1.1045(2) 0.0553(6) Uani 1 1 d . . . . .
N2 N 0.2786(3) 0.2837(2) 0.9146(2) 0.0384(6) Uani 1 1 d . . . . .
C14 C -0.2649(3) 0.1057(2) 0.7938(2) 0.0336(7) Uani 1 1 d . . . . .
C12 C 0.1992(3) 0.4224(2) 1.0260(2) 0.0366(7) Uani 1 1 d . . . . .
N1 N 0.1314(3) 0.34339(19) 1.06342(19) 0.0363(6) Uani 1 1 d . . . . .
C11 C 0.2747(3) 0.3915(2) 0.9478(2) 0.0384(8) Uani 1 1 d . . . . .
C20 C 0.0109(3) -0.0906(3) 0.7920(2) 0.0371(7) Uani 1 1 d . . . . .
C27 C 0.4860(3) 0.2033(2) 1.1594(3) 0.0421(8) Uani 1 1 d . . . . .
C21 C -0.0080(3) -0.1385(2) 0.6787(2) 0.0347(7) Uani 1 1 d . . . . .
C13 C -0.1390(3) 0.1166(2) 0.8768(2) 0.0349(7) Uani 1 1 d . . . . .
C15 C -0.2625(3) 0.1598(3) 0.7109(2) 0.0424(8) Uani 1 1 d . . . . .
H15 H -0.1821 0.2013 0.7071 0.051 Uiso 1 1 calc R U . . .
C18 C -0.5006(3) 0.0365(3) 0.7216(3) 0.0505(9) Uani 1 1 d . . . . .
H18 H -0.5810 -0.0055 0.7245 0.061 Uiso 1 1 calc R U . . .
C17 C -0.4956(3) 0.0915(3) 0.6413(3) 0.0477(9) Uani 1 1 d . . . . .
C7 C 0.3433(4) 0.4728(3) 0.9067(3) 0.0525(9) Uani 1 1 d . . . . .
C4 C 0.1923(4) 0.5336(2) 1.0593(3) 0.0478(9) Uani 1 1 d . . . . .
C16 C -0.3770(3) 0.1528(3) 0.6345(3) 0.0498(9) Uani 1 1 d . . . . .
H16 H -0.3745 0.1889 0.5791 0.060 Uiso 1 1 calc R U . . .
C24 C -0.0457(3) -0.2255(3) 0.4696(2) 0.0481(9) Uani 1 1 d . . . . .
C1 C 0.0569(3) 0.3740(3) 1.1320(3) 0.0468(8) Uani 1 1 d . . . . .
H1 H 0.0104 0.3201 1.1578 0.056 Uiso 1 1 calc R U . . .
C10 C 0.3487(4) 0.2573(3) 0.8429(3) 0.0518(9) Uani 1 1 d . . . . .
H10 H 0.3520 0.1840 0.8208 0.062 Uiso 1 1 calc R U . . .
C25 C -0.1165(4) -0.2762(3) 0.5304(3) 0.0546(10) Uani 1 1 d . . . . .
H25 H -0.1769 -0.3397 0.5018 0.065 Uiso 1 1 calc R U . . .
C28 C 0.5523(3) 0.2653(3) 1.2662(3) 0.0471(9) Uani 1 1 d . . . . .
C19 C -0.3849(3) 0.0442(3) 0.7981(3) 0.0458(8) Uani 1 1 d . . . . .
H19 H -0.3880 0.0075 0.8531 0.055 Uiso 1 1 calc R U . . .
C3 C 0.1118(4) 0.5609(3) 1.1318(3) 0.0594(11) Uani 1 1 d . . . . .
H3 H 0.1051 0.6333 1.1551 0.071 Uiso 1 1 calc R U . . .
C26 C -0.0975(3) -0.2324(3) 0.6345(3) 0.0477(9) Uani 1 1 d . . . . .
H26 H -0.1460 -0.2668 0.6760 0.057 Uiso 1 1 calc R U . . .
C8 C 0.4152(4) 0.4395(3) 0.8299(3) 0.0657(11) Uani 1 1 d . . . . .
H8 H 0.4607 0.4911 0.8008 0.079 Uiso 1 1 calc R U . . .
C22 C 0.0637(3) -0.0884(3) 0.6152(3) 0.0469(8) Uani 1 1 d . . . . .
H22 H 0.1244 -0.0249 0.6433 0.056 Uiso 1 1 calc R U . . .
C2 C 0.0435(4) 0.4812(3) 1.1681(3) 0.0551(10) Uani 1 1 d . . . . .
H2 H -0.0110 0.4980 1.2159 0.066 Uiso 1 1 calc R U . . .
C9 C 0.4194(4) 0.3329(3) 0.7975(3) 0.0654(11) Uani 1 1 d . . . . .
H9 H 0.4674 0.3102 0.7467 0.078 Uiso 1 1 calc R U . . .
C5 C 0.2640(4) 0.6130(3) 1.0175(3) 0.0674(12) Uani 1 1 d . . . . .
H5 H 0.2609 0.6861 1.0408 0.081 Uiso 1 1 calc R U . . .
C33 C 0.6925(4) 0.2847(3) 1.2985(4) 0.0743(13) Uani 1 1 d . . . . .
H33 H 0.7472 0.2593 1.2535 0.089 Uiso 1 1 calc R U . . .
C23 C 0.0451(4) -0.1324(3) 0.5106(3) 0.0537(9) Uani 1 1 d . . . . .
H23 H 0.0936 -0.0992 0.4683 0.064 Uiso 1 1 calc R U . . .
C6 C 0.3358(4) 0.5849(3) 0.9453(4) 0.0690(12) Uani 1 1 d . . . . .
H6 H 0.3820 0.6388 0.9194 0.083 Uiso 1 1 calc R U . . .
C32 C 0.7516(5) 0.3414(4) 1.3972(4) 0.0940(17) Uani 1 1 d . . . . .
H32 H 0.8461 0.3551 1.4181 0.113 Uiso 1 1 calc R U . . .
C29 C 0.4764(4) 0.3039(4) 1.3347(3) 0.0788(13) Uani 1 1 d . . . . .
H29 H 0.3819 0.2925 1.3141 0.095 Uiso 1 1 calc R U . . .
C30 C 0.5361(5) 0.3595(4) 1.4342(4) 0.0956(16) Uani 1 1 d . . . . .
H30 H 0.4823 0.3842 1.4801 0.115 Uiso 1 1 calc R U . . .
C31 C 0.6730(6) 0.3773(4) 1.4639(4) 0.0828(15) Uani 1 1 d . . . . .
HW1 H 0.438(3) 0.083(3) 0.993(2) 0.076(13) Uiso 1 1 d D . . . .
HW2 H 0.364(4) -0.0212(18) 0.920(3) 0.101(16) Uiso 1 1 d D . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
La1 O4 2.437(2) . ?
La1 O5 2.466(2) . ?
La1 O2 2.517(2) . ?
La1 O3 2.517(2) . ?
La1 O1 2.542(2) . ?
La1 OW1 2.551(2) . ?
La1 N2 2.743(2) . ?
La1 N1 2.758(2) . ?
La1 O2 2.818(2) 2_557 ?
La1 C13 3.041(3) . ?
Cl1 C17 1.743(3) . ?
Cl2 C24 1.744(3) . ?
Cl3 C31 1.741(5) . ?
O2 C13 1.274(3) 2_557 ?
O2 La1 2.818(2) 2_557 ?
OW1 HW1 0.954(19) . ?
OW1 HW2 0.931(19) . ?
O3 C20 1.249(4) . ?
O1 C13 1.256(3) . ?
O4 C20 1.264(3) 2_557 ?
O5 C27 1.268(4) . ?
O6 C27 1.247(4) . ?
N2 C10 1.313(4) . ?
N2 C11 1.367(4) . ?
C14 C19 1.380(4) . ?
C14 C15 1.390(4) . ?
C14 C13 1.497(4) . ?
C12 N1 1.359(4) . ?
C12 C4 1.414(4) . ?
C12 C11 1.430(4) . ?
N1 C1 1.323(4) . ?
C11 C7 1.413(4) . ?
C20 O4 1.264(3) 2_557 ?
C20 C21 1.499(4) . ?
C27 C28 1.500(5) . ?
C21 C26 1.379(4) . ?
C21 C22 1.392(4) . ?
C13 O2 1.274(3) 2_557 ?
C15 C16 1.373(4) . ?
C15 H15 0.9300 . ?
C18 C17 1.369(5) . ?
C18 C19 1.381(4) . ?
C18 H18 0.9300 . ?
C17 C16 1.376(4) . ?
C7 C8 1.396(5) . ?
C7 C6 1.439(5) . ?
C4 C3 1.398(5) . ?
C4 C5 1.416(5) . ?
C16 H16 0.9300 . ?
C24 C25 1.362(5) . ?
C24 C23 1.373(5) . ?
C1 C2 1.390(4) . ?
C1 H1 0.9300 . ?
C10 C9 1.406(5) . ?
C10 H10 0.9300 . ?
C25 C26 1.374(4) . ?
C25 H25 0.9300 . ?
C28 C29 1.361(5) . ?
C28 C33 1.382(5) . ?
C19 H19 0.9300 . ?
C3 C2 1.359(5) . ?
C3 H3 0.9300 . ?
C26 H26 0.9300 . ?
C8 C9 1.352(5) . ?
C8 H8 0.9300 . ?
C22 C23 1.382(4) . ?
C22 H22 0.9300 . ?
C2 H2 0.9300 . ?
C9 H9 0.9300 . ?
C5 C6 1.335(6) . ?
C5 H5 0.9300 . ?
C33 C32 1.379(6) . ?
C33 H33 0.9300 . ?
C23 H23 0.9300 . ?
C6 H6 0.9300 . ?
C32 C31 1.353(7) . ?
C32 H32 0.9300 . ?
C29 C30 1.384(6) . ?
C29 H29 0.9300 . ?
C30 C31 1.347(6) . ?
C30 H30 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 La1 O5 80.41(8) . . ?
O4 La1 O2 70.20(7) . . ?
O5 La1 O2 93.38(7) . . ?
O4 La1 O3 133.10(7) . . ?
O5 La1 O3 136.44(7) . . ?
O2 La1 O3 78.35(7) . . ?
O4 La1 O1 98.41(8) . . ?
O5 La1 O1 140.08(7) . . ?
O2 La1 O1 124.07(7) . . ?
O3 La1 O1 71.43(7) . . ?
O4 La1 OW1 134.86(8) . . ?
O5 La1 OW1 69.83(8) . . ?
O2 La1 OW1 78.32(7) . . ?
O3 La1 OW1 66.61(8) . . ?
O1 La1 OW1 126.22(8) . . ?
O4 La1 N2 130.42(8) . . ?
O5 La1 N2 75.51(7) . . ?
O2 La1 N2 152.46(7) . . ?
O3 La1 N2 92.33(7) . . ?
O1 La1 N2 75.51(7) . . ?
OW1 La1 N2 74.21(8) . . ?
O4 La1 N1 71.95(7) . . ?
O5 La1 N1 73.45(7) . . ?
O2 La1 N1 141.48(7) . . ?
O3 La1 N1 135.58(7) . . ?
O1 La1 N1 68.45(7) . . ?
OW1 La1 N1 126.67(8) . . ?
N2 La1 N1 59.93(8) . . ?
O4 La1 O2 71.15(7) . 2_557 ?
O5 La1 O2 151.56(7) . 2_557 ?
O2 La1 O2 77.23(7) . 2_557 ?
O3 La1 O2 68.54(7) . 2_557 ?
O1 La1 O2 48.33(6) . 2_557 ?
OW1 La1 O2 132.15(7) . 2_557 ?
N2 La1 O2 123.64(7) . 2_557 ?
N1 La1 O2 97.16(7) . 2_557 ?
O4 La1 C13 87.08(8) . . ?
O5 La1 C13 157.07(7) . . ?
O2 La1 C13 100.39(8) . . ?
O3 La1 C13 65.06(7) . . ?
O1 La1 C13 23.93(7) . . ?
OW1 La1 C13 130.79(8) . . ?
N2 La1 C13 98.91(8) . . ?
N1 La1 C13 84.46(7) . . ?
O2 La1 C13 24.74(6) 2_557 . ?
O4 La1 La1 65.00(5) . 2_557 ?
O5 La1 La1 129.01(5) . 2_557 ?
O2 La1 La1 41.20(5) . 2_557 ?
O3 La1 La1 68.36(5) . 2_557 ?
O1 La1 La1 83.62(5) . 2_557 ?
OW1 La1 La1 109.34(6) . 2_557 ?
N2 La1 La1 155.36(5) . 2_557 ?
N1 La1 La1 123.78(5) . 2_557 ?
O2 La1 La1 36.03(4) 2_557 2_557 ?
C13 La1 La1 59.69(6) . 2_557 ?
C13 O2 La1 156.9(2) 2_557 . ?
C13 O2 La1 87.47(18) 2_557 2_557 ?
La1 O2 La1 102.77(7) . 2_557 ?
La1 OW1 HW1 111(2) . . ?
La1 OW1 HW2 129(3) . . ?
HW1 OW1 HW2 108(3) . . ?
C20 O3 La1 135.4(2) . . ?
C13 O1 La1 100.91(18) . . ?
C20 O4 La1 143.8(2) 2_557 . ?
C27 O5 La1 146.0(2) . . ?
C10 N2 C11 117.9(3) . . ?
C10 N2 La1 120.9(2) . . ?
C11 N2 La1 121.2(2) . . ?
C19 C14 C15 118.7(3) . . ?
C19 C14 C13 121.6(3) . . ?
C15 C14 C13 119.7(3) . . ?
N1 C12 C4 121.7(3) . . ?
N1 C12 C11 118.8(3) . . ?
C4 C12 C11 119.4(3) . . ?
C1 N1 C12 117.5(3) . . ?
C1 N1 La1 121.5(2) . . ?
C12 N1 La1 120.99(19) . . ?
N2 C11 C7 121.6(3) . . ?
N2 C11 C12 119.0(3) . . ?
C7 C11 C12 119.3(3) . . ?
O3 C20 O4 124.9(3) . 2_557 ?
O3 C20 C21 118.8(3) . . ?
O4 C20 C21 116.2(3) 2_557 . ?
O6 C27 O5 124.6(3) . . ?
O6 C27 C28 119.2(3) . . ?
O5 C27 C28 116.2(3) . . ?
C26 C21 C22 118.4(3) . . ?
C26 C21 C20 121.1(3) . . ?
C22 C21 C20 120.5(3) . . ?
O1 C13 O2 121.6(3) . 2_557 ?
O1 C13 C14 118.5(3) . . ?
O2 C13 C14 119.9(3) 2_557 . ?
O1 C13 La1 55.16(15) . . ?
O2 C13 La1 67.80(16) 2_557 . ?
C14 C13 La1 165.7(2) . . ?
C16 C15 C14 121.0(3) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C17 C18 C19 119.3(3) . . ?
C17 C18 H18 120.4 . . ?
C19 C18 H18 120.4 . . ?
C18 C17 C16 121.3(3) . . ?
C18 C17 Cl1 119.8(3) . . ?
C16 C17 Cl1 118.9(3) . . ?
C8 C7 C11 117.7(3) . . ?
C8 C7 C6 123.4(3) . . ?
C11 C7 C6 118.9(4) . . ?
C3 C4 C12 118.1(3) . . ?
C3 C4 C5 122.2(3) . . ?
C12 C4 C5 119.7(4) . . ?
C15 C16 C17 119.0(3) . . ?
C15 C16 H16 120.5 . . ?
C17 C16 H16 120.5 . . ?
C25 C24 C23 121.3(3) . . ?
C25 C24 Cl2 119.6(3) . . ?
C23 C24 Cl2 119.1(3) . . ?
N1 C1 C2 124.5(3) . . ?
N1 C1 H1 117.8 . . ?
C2 C1 H1 117.8 . . ?
N2 C10 C9 124.1(3) . . ?
N2 C10 H10 117.9 . . ?
C9 C10 H10 117.9 . . ?
C24 C25 C26 119.2(3) . . ?
C24 C25 H25 120.4 . . ?
C26 C25 H25 120.4 . . ?
C29 C28 C33 117.8(4) . . ?
C29 C28 C27 121.1(3) . . ?
C33 C28 C27 121.1(4) . . ?
C14 C19 C18 120.7(3) . . ?
C14 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C2 C3 C4 119.7(3) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C25 C26 C21 121.5(3) . . ?
C25 C26 H26 119.3 . . ?
C21 C26 H26 119.3 . . ?
C9 C8 C7 120.6(3) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C23 C22 C21 120.3(3) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C3 C2 C1 118.4(4) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C8 C9 C10 118.0(4) . . ?
C8 C9 H9 121.0 . . ?
C10 C9 H9 121.0 . . ?
C6 C5 C4 121.2(4) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C32 C33 C28 120.2(4) . . ?
C32 C33 H33 119.9 . . ?
C28 C33 H33 119.9 . . ?
C24 C23 C22 119.4(3) . . ?
C24 C23 H23 120.3 . . ?
C22 C23 H23 120.3 . . ?
C5 C6 C7 121.4(4) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C31 C32 C33 120.4(4) . . ?
C31 C32 H32 119.8 . . ?
C33 C32 H32 119.8 . . ?
C28 C29 C30 121.8(4) . . ?
C28 C29 H29 119.1 . . ?
C30 C29 H29 119.1 . . ?
C31 C30 C29 119.3(5) . . ?
C31 C30 H30 120.4 . . ?
C29 C30 H30 120.4 . . ?
C30 C31 C32 120.5(5) . . ?
C30 C31 Cl3 119.7(5) . . ?
C32 C31 Cl3 119.8(4) . . ?

_refine_diff_density_max         0.521
_refine_diff_density_min         -0.544
_refine_diff_density_rms         0.087

_shelxl_version_number           2013-4

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_h-m   'P -1'
_symmetry_int_tables_number      2
_chemical_absolute_configuration ?
_database_code_depnum_ccdc_archive 'CCDC 1018738'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_Compound_2



_audit_creation_method           SHELXL-2013
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C66 H44 Ce2 Cl6 N4 O14'
_chemical_melting_point          ?

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colorless

_diffrn_ambient_temperature      293(2)
_chemical_formula_weight         1609.99

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

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

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

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

_cell_length_a                   8.4595(5)
_cell_length_b                   12.9231(8)
_cell_length_c                   15.4404(9)
_cell_angle_alpha                98.995(6)
_cell_angle_beta                 100.654(7)
_cell_angle_gamma                100.680(6)
_cell_volume                     1598.09(17)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    21251
_cell_measurement_theta_min      4.663
_cell_measurement_theta_max      42.862
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.673
_exptl_crystal_F_000             798
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    1.726
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6562
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS, Bruker-AXS (2008)'

_exptl_special_details           
;
 ?
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21250
_diffrn_reflns_av_unetI/netI     0.0656
_diffrn_reflns_av_R_equivalents  0.0530
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.369
_diffrn_reflns_theta_max         27.608
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7386
_reflns_number_gt                5896
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX, Bruker-AXS'
_computing_cell_refinement       'SAINT, Bruker-AXS'
_computing_data_reduction        'SAINT, Bruker-AXS'
_computing_structure_solution    'SIR92 (Gualardi, 1994)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Crystal Maker (Palmer, 2009)'
_computing_publication_material  'WINGX (Farrugia, 2012)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0304P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7386
_refine_ls_number_parameters     423
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0570
_refine_ls_R_factor_gt           0.0384
_refine_ls_wR_factor_ref         0.0755
_refine_ls_wR_factor_gt          0.0688
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_restrained_S_all      0.995
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ce1 Ce 0.79554(2) 0.36922(2) 0.48194(2) 0.02544(7) Uani 1 1 d . . . . .
Cl1 Cl 0.83023(18) 0.28179(13) -0.05942(8) 0.0881(5) Uani 1 1 d . . . . .
Cl3 Cl 0.2016(2) 0.00987(17) -0.06788(10) 0.1207(7) Uani 1 1 d . . . . .
Cl2 Cl 0.5678(2) 0.6553(2) 0.01650(11) 0.1336(8) Uani 1 1 d . . . . .
OW1 O 0.5129(3) 0.3720(2) 0.50943(19) 0.0393(6) Uani 1 1 d D . . . .
O3 O 0.7118(3) 0.52069(19) 0.41953(16) 0.0351(6) Uani 1 1 d . . . . .
O5 O 0.5904(3) 0.2664(2) 0.34861(17) 0.0411(6) Uani 1 1 d . . . . .
O1 O 0.9889(3) 0.42897(19) 0.39049(16) 0.0362(6) Uani 1 1 d . . . . .
O4 O 1.0627(3) 0.35254(19) 0.56719(17) 0.0388(6) Uani 1 1 d . . . . .
N1 N 0.8683(4) 0.1804(2) 0.4184(2) 0.0348(7) Uani 1 1 d . . . . .
O6 O 0.3440(3) 0.3065(3) 0.34274(19) 0.0619(9) Uani 1 1 d . . . . .
N2 N 0.7220(4) 0.2024(2) 0.5628(2) 0.0388(8) Uani 1 1 d . . . . .
C3 C 0.9013(6) -0.0196(4) 0.3365(3) 0.0648(14) Uani 1 1 d . . . . .
H3 H 0.9092 -0.0865 0.3073 0.078 Uiso 1 1 calc R U . . .
C1 C 0.9429(5) 0.1692(3) 0.3510(3) 0.0450(10) Uani 1 1 d . . . . .
H1 H 0.9867 0.2307 0.3316 0.054 Uiso 1 1 calc R U . . .
C14 C 0.9996(4) 0.4230(3) 0.2364(2) 0.0310(8) Uani 1 1 d . . . . .
C11 C 0.7413(4) 0.1029(3) 0.5273(3) 0.0392(9) Uani 1 1 d . . . . .
C28 C 0.3853(5) 0.1994(3) 0.2152(3) 0.0372(9) Uani 1 1 d . . . . .
C16 C 0.8010(5) 0.3031(3) 0.1128(3) 0.0517(11) Uani 1 1 d . . . . .
H16 H 0.7040 0.2508 0.0913 0.062 Uiso 1 1 calc R U . . .
C15 C 0.8542(5) 0.3464(3) 0.2041(3) 0.0395(9) Uani 1 1 d . . . . .
H15 H 0.7914 0.3236 0.2438 0.047 Uiso 1 1 calc R U . . .
C12 C 0.8129(4) 0.0909(3) 0.4502(3) 0.0374(9) Uani 1 1 d . . . . .
O2 O 0.8133(3) 0.4552(2) 0.64094(17) 0.0428(7) Uani 1 1 d . . . . .
C21 C 0.7371(4) 0.6101(3) 0.2986(2) 0.0334(8) Uani 1 1 d . . . . .
C2 C 0.9604(6) 0.0696(4) 0.3065(3) 0.0591(13) Uani 1 1 d . . . . .
H2 H 1.0112 0.0652 0.2580 0.071 Uiso 1 1 calc R U . . .
C26 C 0.8416(5) 0.6725(3) 0.2576(3) 0.0458(10) Uani 1 1 d . . . . .
H26 H 0.9486 0.7050 0.2891 0.055 Uiso 1 1 calc R U . . .
C13 C 1.0632(4) 0.4685(3) 0.3349(2) 0.0320(8) Uani 1 1 d . . . . .
C27 C 0.4435(5) 0.2634(3) 0.3093(3) 0.0377(9) Uani 1 1 d . . . . .
C33 C 0.2416(5) 0.2105(4) 0.1617(3) 0.0534(11) Uani 1 1 d . . . . .
H33 H 0.1816 0.2573 0.1848 0.064 Uiso 1 1 calc R U . . .
C10 C 0.6621(5) 0.2136(4) 0.6360(3) 0.0519(11) Uani 1 1 d . . . . .
H10 H 0.6500 0.2813 0.6607 0.062 Uiso 1 1 calc R U . . .
C19 C 1.0890(5) 0.4584(3) 0.1756(3) 0.0434(10) Uani 1 1 d . . . . .
H19 H 1.1853 0.5115 0.1961 0.052 Uiso 1 1 calc R U . . .
C4 C 0.8289(5) -0.0125(3) 0.4103(3) 0.0517(12) Uani 1 1 d . . . . .
C30 C 0.4097(6) 0.0644(4) 0.0951(3) 0.0644(13) Uani 1 1 d . . . . .
H30 H 0.4634 0.0125 0.0736 0.077 Uiso 1 1 calc R U . . .
C20 C 0.8002(4) 0.5913(3) 0.3904(2) 0.0302(8) Uani 1 1 d . . . . .
C29 C 0.4673(5) 0.1256(3) 0.1810(3) 0.0486(11) Uani 1 1 d . . . . .
H29 H 0.5635 0.1166 0.2165 0.058 Uiso 1 1 calc R U . . .
C7 C 0.6932(5) 0.0118(3) 0.5639(3) 0.0536(12) Uani 1 1 d . . . . .
C24 C 0.6328(6) 0.6396(5) 0.1263(3) 0.0739(16) Uani 1 1 d . . . . .
C23 C 0.5269(6) 0.5773(5) 0.1649(3) 0.092(2) Uani 1 1 d . . . . .
H23 H 0.4200 0.5452 0.1329 0.110 Uiso 1 1 calc R U . . .
C18 C 1.0359(5) 0.4153(4) 0.0851(3) 0.0535(11) Uani 1 1 d . . . . .
H18 H 1.0969 0.4386 0.0448 0.064 Uiso 1 1 calc R U . . .
C31 C 0.2716(6) 0.0819(4) 0.0422(3) 0.0678(14) Uani 1 1 d . . . . .
C9 C 0.6154(6) 0.1271(4) 0.6785(3) 0.0683(14) Uani 1 1 d . . . . .
H9 H 0.5754 0.1376 0.7307 0.082 Uiso 1 1 calc R U . . .
C25 C 0.7896(6) 0.6870(4) 0.1716(3) 0.0592(12) Uani 1 1 d . . . . .
H25 H 0.8607 0.7285 0.1447 0.071 Uiso 1 1 calc R U . . .
C22 C 0.5796(5) 0.5625(4) 0.2511(3) 0.0585(13) Uani 1 1 d . . . . .
H22 H 0.5081 0.5200 0.2772 0.070 Uiso 1 1 calc R U . . .
C17 C 0.8935(5) 0.3385(4) 0.0549(3) 0.0508(11) Uani 1 1 d . . . . .
C8 C 0.6308(6) 0.0280(4) 0.6409(4) 0.0710(16) Uani 1 1 d . . . . .
H8 H 0.5988 -0.0301 0.6673 0.085 Uiso 1 1 calc R U . . .
C6 C 0.7113(6) -0.0912(4) 0.5216(4) 0.0684(15) Uani 1 1 d . . . . .
H6 H 0.6775 -0.1514 0.5452 0.082 Uiso 1 1 calc R U . . .
C32 C 0.1856(6) 0.1532(4) 0.0744(3) 0.0696(14) Uani 1 1 d . . . . .
H32 H 0.0908 0.1630 0.0382 0.083 Uiso 1 1 calc R U . . .
C5 C 0.7752(6) -0.1018(3) 0.4494(4) 0.0710(15) Uani 1 1 d . . . . .
H5 H 0.7854 -0.1696 0.4236 0.085 Uiso 1 1 calc R U . . .
HW1 H 0.433(5) 0.354(4) 0.453(2) 0.091(18) Uiso 1 1 d D . . . .
HW2 H 0.477(5) 0.424(3) 0.547(2) 0.072(15) Uiso 1 1 d D . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ce1 O5 2.446(2) . ?
Ce1 O1 2.448(2) . ?
Ce1 O4 2.461(2) . ?
Ce1 O3 2.472(2) . ?
Ce1 O2 2.497(2) . ?
Ce1 OW1 2.511(3) . ?
Ce1 N2 2.688(3) . ?
Ce1 N1 2.706(3) . ?
Cl1 C17 1.743(4) . ?
Cl3 C31 1.742(5) . ?
Cl2 C24 1.739(5) . ?
O3 C20 1.263(4) . ?
O5 C27 1.269(4) . ?
O1 C13 1.269(4) . ?
O4 C20 1.249(4) 2_766 ?
N1 C1 1.317(5) . ?
N1 C12 1.363(4) . ?
O6 C27 1.237(4) . ?
N2 C10 1.320(5) . ?
N2 C11 1.368(5) . ?
C3 C2 1.353(6) . ?
C3 C4 1.388(6) . ?
C1 C2 1.408(5) . ?
C14 C15 1.381(5) . ?
C14 C19 1.391(5) . ?
C14 C13 1.499(5) . ?
C11 C7 1.410(5) . ?
C11 C12 1.433(5) . ?
C28 C29 1.377(5) . ?
C28 C33 1.382(5) . ?
C28 C27 1.499(5) . ?
C16 C17 1.370(6) . ?
C16 C15 1.389(5) . ?
C12 C4 1.423(5) . ?
O2 C13 1.250(4) 2_766 ?
C21 C22 1.374(5) . ?
C21 C26 1.390(5) . ?
C21 C20 1.493(5) . ?
C26 C25 1.373(5) . ?
C13 O2 1.250(4) 2_766 ?
C33 C32 1.383(6) . ?
C10 C9 1.413(6) . ?
C19 C18 1.377(5) . ?
C4 C5 1.425(6) . ?
C30 C31 1.373(6) . ?
C30 C29 1.383(6) . ?
C20 O4 1.249(4) 2_766 ?
C7 C8 1.390(7) . ?
C7 C6 1.436(7) . ?
C24 C25 1.359(6) . ?
C24 C23 1.373(7) . ?
C23 C22 1.378(6) . ?
C18 C17 1.363(6) . ?
C31 C32 1.366(7) . ?
C9 C8 1.361(7) . ?
C6 C5 1.325(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O5 Ce1 O1 91.74(8) . . ?
O5 Ce1 O4 136.55(8) . . ?
O1 Ce1 O4 76.57(8) . . ?
O5 Ce1 O3 81.28(8) . . ?
O1 Ce1 O3 71.94(8) . . ?
O4 Ce1 O3 131.10(8) . . ?
O5 Ce1 O2 140.10(8) . . ?
O1 Ce1 O2 124.66(8) . . ?
O4 Ce1 O2 74.28(8) . . ?
O3 Ce1 O2 94.11(8) . . ?
O5 Ce1 OW1 71.23(9) . . ?
O1 Ce1 OW1 143.62(9) . . ?
O4 Ce1 OW1 137.47(9) . . ?
O3 Ce1 OW1 73.78(8) . . ?
O2 Ce1 OW1 69.45(9) . . ?
O5 Ce1 N2 87.75(9) . . ?
O1 Ce1 N2 137.73(9) . . ?
O4 Ce1 N2 75.15(9) . . ?
O3 Ce1 N2 148.95(9) . . ?
O2 Ce1 N2 76.00(9) . . ?
OW1 Ce1 N2 75.19(9) . . ?
O5 Ce1 N1 67.89(8) . . ?
O1 Ce1 N1 79.60(9) . . ?
O4 Ce1 N1 68.87(8) . . ?
O3 Ce1 N1 137.04(9) . . ?
O2 Ce1 N1 128.75(9) . . ?
OW1 Ce1 N1 119.79(9) . . ?
N2 Ce1 N1 61.17(9) . . ?
C20 O3 Ce1 127.2(2) . . ?
C27 O5 Ce1 138.7(2) . . ?
C13 O1 Ce1 167.2(2) . . ?
C20 O4 Ce1 140.9(2) 2_766 . ?
C1 N1 C12 117.9(3) . . ?
C1 N1 Ce1 121.8(2) . . ?
C12 N1 Ce1 120.0(2) . . ?
C10 N2 C11 118.4(3) . . ?
C10 N2 Ce1 121.0(3) . . ?
C11 N2 Ce1 120.5(2) . . ?
C2 C3 C4 120.8(4) . . ?
N1 C1 C2 123.9(4) . . ?
C15 C14 C19 118.8(3) . . ?
C15 C14 C13 121.9(3) . . ?
C19 C14 C13 119.3(3) . . ?
N2 C11 C7 122.3(4) . . ?
N2 C11 C12 118.8(3) . . ?
C7 C11 C12 118.8(4) . . ?
C29 C28 C33 118.3(4) . . ?
C29 C28 C27 121.8(3) . . ?
C33 C28 C27 119.9(4) . . ?
C17 C16 C15 119.1(4) . . ?
C14 C15 C16 120.6(4) . . ?
N1 C12 C4 121.7(4) . . ?
N1 C12 C11 118.5(3) . . ?
C4 C12 C11 119.8(4) . . ?
C13 O2 Ce1 108.7(2) 2_766 . ?
C22 C21 C26 118.6(4) . . ?
C22 C21 C20 121.5(3) . . ?
C26 C21 C20 119.8(3) . . ?
C3 C2 C1 118.1(4) . . ?
C25 C26 C21 121.2(4) . . ?
O2 C13 O1 122.4(3) 2_766 . ?
O2 C13 C14 118.7(3) 2_766 . ?
O1 C13 C14 118.9(3) . . ?
O6 C27 O5 125.6(4) . . ?
O6 C27 C28 117.6(3) . . ?
O5 C27 C28 116.7(3) . . ?
C32 C33 C28 121.2(4) . . ?
N2 C10 C9 122.9(4) . . ?
C18 C19 C14 120.4(4) . . ?
C3 C4 C12 117.6(4) . . ?
C3 C4 C5 123.7(4) . . ?
C12 C4 C5 118.7(5) . . ?
C31 C30 C29 118.6(4) . . ?
O4 C20 O3 124.8(3) 2_766 . ?
O4 C20 C21 117.0(3) 2_766 . ?
O3 C20 C21 118.1(3) . . ?
C28 C29 C30 121.4(4) . . ?
C8 C7 C11 116.9(4) . . ?
C8 C7 C6 123.5(4) . . ?
C11 C7 C6 119.7(5) . . ?
C25 C24 C23 121.2(4) . . ?
C25 C24 Cl2 119.2(4) . . ?
C23 C24 Cl2 119.6(4) . . ?
C24 C23 C22 119.7(4) . . ?
C17 C18 C19 119.8(4) . . ?
C32 C31 C30 121.5(4) . . ?
C32 C31 Cl3 119.0(4) . . ?
C30 C31 Cl3 119.5(4) . . ?
C8 C9 C10 118.0(5) . . ?
C24 C25 C26 119.0(4) . . ?
C21 C22 C23 120.3(4) . . ?
C18 C17 C16 121.3(4) . . ?
C18 C17 Cl1 119.4(3) . . ?
C16 C17 Cl1 119.2(3) . . ?
C9 C8 C7 121.5(4) . . ?
C5 C6 C7 121.1(4) . . ?
C31 C32 C33 118.9(4) . . ?
C6 C5 C4 121.9(5) . . ?

_refine_diff_density_max         0.708
_refine_diff_density_min         -0.690
_refine_diff_density_rms         0.103

_shelxl_version_number           2013-4

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_h-m   'P -1'
_symmetry_int_tables_number      2
_chemical_absolute_configuration ?
_database_code_depnum_ccdc_archive 'CCDC 1018739'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_Compound_3



_audit_creation_method           SHELXL-2013
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C66 H44 Cl6 N4 Nd2 O14'
_chemical_melting_point          ?

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colorless

_diffrn_ambient_temperature      293(2)
_chemical_formula_weight         1618.23

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

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

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

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

_cell_length_a                   8.4411(3)
_cell_length_b                   12.9074(4)
_cell_length_c                   15.4508(5)
_cell_angle_alpha                98.9760(10)
_cell_angle_beta                 100.8290(10)
_cell_angle_gamma                100.727(2)
_cell_volume                     1592.40(9)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    23852
_cell_measurement_theta_min      4.668
_cell_measurement_theta_max      46.286
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.687
_exptl_crystal_F_000             802
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    1.933
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6633
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   'SADABS, Bruker-AXS (2008)'

_exptl_special_details           
;
 ?
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23841
_diffrn_reflns_av_unetI/netI     0.0588
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.638
_diffrn_reflns_theta_max         30.460
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.914
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.914
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.914
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8831
_reflns_number_gt                7117
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX, Bruker-AXS'
_computing_cell_refinement       'SAINT, Bruker-AXS'
_computing_data_reduction        'SAINT, Bruker-AXS'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Crystal Maker (Palmer, 2009)'
_computing_publication_material  'WINGX (Farrugia, 2012)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0245P)²+0.2010P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8831
_refine_ls_number_parameters     423
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0532
_refine_ls_R_factor_gt           0.0370
_refine_ls_wR_factor_ref         0.0716
_refine_ls_wR_factor_gt          0.0653
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Nd1 Nd 0.70607(2) 0.63177(2) 0.51864(2) 0.02610(5) Uani 1 1 d . . . . .
Cl2 Cl 0.66508(15) 0.71526(11) 1.05980(7) 0.0883(4) Uani 1 1 d . . . . .
Cl3 Cl 1.29782(18) 0.98825(15) 1.06838(9) 0.1250(6) Uani 1 1 d . . . . .
Cl1 Cl 0.06742(18) 0.65468(17) 0.01890(9) 0.1309(7) Uani 1 1 d . . . . .
O6 O 1.1564(3) 0.6938(2) 0.65635(17) 0.0625(7) Uani 1 1 d . . . . .
O1 O 0.4412(2) 0.64667(16) 0.43528(14) 0.0378(5) Uani 1 1 d . . . . .
O4 O 0.5196(3) 0.57502(17) 0.61039(14) 0.0373(5) Uani 1 1 d . . . . .
O5 O 0.9089(2) 0.73265(17) 0.65023(14) 0.0424(5) Uani 1 1 d . . . . .
N1 N 0.6349(3) 0.81926(19) 0.58088(18) 0.0371(6) Uani 1 1 d . . . . .
C21 C 0.5022(3) 0.5781(2) 0.76264(19) 0.0308(6) Uani 1 1 d . . . . .
C13 C 0.3015(4) 0.5913(2) 0.3936(2) 0.0305(6) Uani 1 1 d . . . . .
N2 N 0.7785(3) 0.7940(2) 0.43630(18) 0.0393(6) Uani 1 1 d . . . . .
C26 C 0.6481(4) 0.6547(3) 0.7969(2) 0.0412(8) Uani 1 1 d . . . . .
H26 H 0.7126 0.6785 0.7582 0.049 Uiso 1 1 calc R U . . .
C20 C 0.4413(4) 0.5342(2) 0.6638(2) 0.0329(7) Uani 1 1 d . . . . .
C11 C 0.6900(4) 0.9075(2) 0.5482(2) 0.0398(8) Uani 1 1 d . . . . .
C14 C 0.2379(4) 0.6102(2) 0.3016(2) 0.0328(7) Uani 1 1 d . . . . .
C29 C 1.0313(4) 0.8732(3) 0.8186(2) 0.0487(9) Uani 1 1 d . . . . .
H29 H 0.9342 0.8815 0.7831 0.058 Uiso 1 1 calc R U . . .
C12 C 0.7606(4) 0.8941(3) 0.4709(2) 0.0422(8) Uani 1 1 d . . . . .
C27 C 1.0563(4) 0.7368(3) 0.6904(2) 0.0385(7) Uani 1 1 d . . . . .
C22 C 0.4107(4) 0.5409(3) 0.8217(2) 0.0455(8) Uani 1 1 d . . . . .
H22 H 0.3145 0.4875 0.7995 0.055 Uiso 1 1 calc R U . . .
C28 C 1.1150(4) 0.8002(3) 0.7845(2) 0.0376(7) Uani 1 1 d . . . . .
C25 C 0.6987(4) 0.6960(3) 0.8879(2) 0.0532(9) Uani 1 1 d . . . . .
H25 H 0.7963 0.7481 0.9106 0.064 Uiso 1 1 calc R U . . .
C15 C 0.3409(4) 0.6728(3) 0.2612(2) 0.0453(8) Uani 1 1 d . . . . .
H15 H 0.4480 0.7057 0.2931 0.054 Uiso 1 1 calc R U . . .
C23 C 0.4606(5) 0.5818(3) 0.9130(2) 0.0560(10) Uani 1 1 d . . . . .
H23 H 0.3982 0.5570 0.9523 0.067 Uiso 1 1 calc R U . . .
C10 C 0.8371(4) 0.7815(3) 0.3629(3) 0.0522(9) Uani 1 1 d . . . . .
H10 H 0.8495 0.7134 0.3392 0.063 Uiso 1 1 calc R U . . .
C30 C 1.0894(5) 0.9345(3) 0.9048(3) 0.0642(11) Uani 1 1 d . . . . .
H30 H 1.0357 0.9862 0.9266 0.077 Uiso 1 1 calc R U . . .
C2 C 0.5452(5) 0.9313(3) 0.6919(3) 0.0611(11) Uani 1 1 d . . . . .
H2 H 0.4955 0.9364 0.7407 0.073 Uiso 1 1 calc R U . . .
C1 C 0.5609(4) 0.8320(3) 0.6488(2) 0.0455(8) Uani 1 1 d . . . . .
H1 H 0.5169 0.7710 0.6689 0.055 Uiso 1 1 calc R U . . .
C24 C 0.6037(5) 0.6597(3) 0.9447(2) 0.0515(9) Uani 1 1 d . . . . .
C33 C 1.2587(4) 0.7894(3) 0.8383(2) 0.0557(10) Uani 1 1 d . . . . .
H33 H 1.3191 0.7428 0.8153 0.067 Uiso 1 1 calc R U . . .
C7 C 0.8077(4) 0.9842(3) 0.4324(3) 0.0564(10) Uani 1 1 d . . . . .
C8 C 0.8687(5) 0.9663(4) 0.3550(3) 0.0740(14) Uani 1 1 d . . . . .
H8 H 0.9010 1.0236 0.3277 0.089 Uiso 1 1 calc R U . . .
C4 C 0.6747(4) 1.0112(3) 0.5871(3) 0.0540(10) Uani 1 1 d . . . . .
C31 C 1.2290(5) 0.9165(4) 0.9575(3) 0.0675(12) Uani 1 1 d . . . . .
C16 C 0.2897(5) 0.6882(3) 0.1751(3) 0.0601(11) Uani 1 1 d . . . . .
H16 H 0.3605 0.7311 0.1489 0.072 Uiso 1 1 calc R U . . .
C19 C 0.0797(4) 0.5602(3) 0.2530(2) 0.0578(11) Uani 1 1 d . . . . .
H19 H 0.0089 0.5162 0.2784 0.069 Uiso 1 1 calc R U . . .
C17 C 0.1331(5) 0.6390(4) 0.1292(3) 0.0713(13) Uani 1 1 d . . . . .
O2 O 0.7863(2) 0.47973(16) 0.57728(14) 0.0349(5) Uani 1 1 d . . . . .
OW1 O 0.9859(3) 0.62870(18) 0.49042(16) 0.0391(5) Uani 1 1 d D . . . .
O3 O 0.6824(3) 0.54183(18) 0.36305(14) 0.0435(6) Uani 1 1 d . . . . .
C6 C 0.7918(5) 1.0879(3) 0.4744(3) 0.0684(13) Uani 1 1 d . . . . .
H6 H 0.8260 1.1476 0.4502 0.082 Uiso 1 1 calc R U . . .
C5 C 0.7287(5) 1.1006(3) 0.5476(3) 0.0725(13) Uani 1 1 d . . . . .
H5 H 0.7198 1.1689 0.5731 0.087 Uiso 1 1 calc R U . . .
C32 C 1.3144(5) 0.8463(4) 0.9256(3) 0.0709(12) Uani 1 1 d . . . . .
H32 H 1.4094 0.8364 0.9619 0.085 Uiso 1 1 calc R U . . .
C9 C 0.8817(5) 0.8662(4) 0.3188(3) 0.0694(12) Uani 1 1 d . . . . .
H9 H 0.9192 0.8540 0.2661 0.083 Uiso 1 1 calc R U . . .
C18 C 0.0272(5) 0.5755(4) 0.1669(3) 0.0858(16) Uani 1 1 d . . . . .
H18 H -0.0797 0.5429 0.1345 0.103 Uiso 1 1 calc R U . . .
C3 C 0.6037(5) 1.0204(3) 0.6613(3) 0.0678(12) Uani 1 1 d . . . . .
H3 H 0.5964 1.0877 0.6900 0.081 Uiso 1 1 calc R U . . .
HW1 H 1.022(4) 0.579(2) 0.453(2) 0.061(11) Uiso 1 1 d D . . . .
HW2 H 1.052(4) 0.647(3) 0.5489(16) 0.089(15) Uiso 1 1 d D . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Nd1 O4 2.3995(19) . ?
Nd1 O5 2.408(2) . ?
Nd1 O1 2.419(2) . ?
Nd1 O2 2.4391(19) . ?
Nd1 O3 2.456(2) . ?
Nd1 OW1 2.488(2) . ?
Nd1 N2 2.650(2) . ?
Nd1 N1 2.678(2) . ?
Cl2 C24 1.750(3) . ?
Cl3 C31 1.750(4) . ?
Cl1 C17 1.746(4) . ?
O6 C27 1.244(4) . ?
O1 C13 1.254(3) . ?
O4 C20 1.268(3) . ?
O5 C27 1.269(4) . ?
N1 C1 1.322(4) . ?
N1 C11 1.356(4) . ?
C21 C26 1.383(4) . ?
C21 C22 1.387(4) . ?
C21 C20 1.498(4) . ?
C13 O2 1.262(3) 2_666 ?
C13 C14 1.496(4) . ?
N2 C10 1.319(4) . ?
N2 C12 1.366(4) . ?
C26 C25 1.378(4) . ?
C20 O3 1.247(3) 2_666 ?
C11 C4 1.419(5) . ?
C11 C12 1.432(5) . ?
C14 C15 1.377(4) . ?
C14 C19 1.384(4) . ?
C29 C28 1.377(4) . ?
C29 C30 1.387(5) . ?
C12 C7 1.413(4) . ?
C27 C28 1.495(4) . ?
C22 C23 1.381(5) . ?
C28 C33 1.379(4) . ?
C25 C24 1.374(5) . ?
C15 C16 1.377(5) . ?
C23 C24 1.372(5) . ?
C10 C9 1.406(5) . ?
C30 C31 1.380(5) . ?
C2 C3 1.355(6) . ?
C2 C1 1.391(5) . ?
C33 C32 1.380(5) . ?
C7 C8 1.393(6) . ?
C7 C6 1.435(6) . ?
C8 C9 1.358(6) . ?
C4 C3 1.388(6) . ?
C4 C5 1.429(5) . ?
C31 C32 1.350(6) . ?
C16 C17 1.360(5) . ?
C19 C18 1.377(5) . ?
C17 C18 1.373(5) . ?
O2 C13 1.262(3) 2_666 ?
O3 C20 1.247(3) 2_666 ?
C6 C5 1.337(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 Nd1 O5 90.62(7) . . ?
O4 Nd1 O1 76.75(7) . . ?
O5 Nd1 O1 136.82(7) . . ?
O4 Nd1 O2 72.11(7) . . ?
O5 Nd1 O2 82.22(7) . . ?
O1 Nd1 O2 129.79(7) . . ?
O4 Nd1 O3 123.91(7) . . ?
O5 Nd1 O3 141.34(7) . . ?
O1 Nd1 O3 74.13(7) . . ?
O2 Nd1 O3 91.85(7) . . ?
O4 Nd1 OW1 143.48(7) . . ?
O5 Nd1 OW1 71.65(7) . . ?
O1 Nd1 OW1 137.49(8) . . ?
O2 Nd1 OW1 73.97(7) . . ?
O3 Nd1 OW1 70.00(7) . . ?
O4 Nd1 N2 138.32(8) . . ?
O5 Nd1 N2 88.73(8) . . ?
O1 Nd1 N2 75.58(7) . . ?
O2 Nd1 N2 148.58(7) . . ?
O3 Nd1 N2 76.68(8) . . ?
OW1 Nd1 N2 74.62(8) . . ?
O4 Nd1 N1 79.40(7) . . ?
O5 Nd1 N1 68.06(7) . . ?
O1 Nd1 N1 69.07(7) . . ?
O2 Nd1 N1 138.29(8) . . ?
O3 Nd1 N1 129.62(8) . . ?
OW1 Nd1 N1 119.76(8) . . ?
N2 Nd1 N1 61.86(8) . . ?
C13 O1 Nd1 142.08(18) . . ?
C20 O4 Nd1 168.71(19) . . ?
C27 O5 Nd1 139.6(2) . . ?
C1 N1 C11 117.9(3) . . ?
C1 N1 Nd1 122.3(2) . . ?
C11 N1 Nd1 119.5(2) . . ?
C26 C21 C22 118.9(3) . . ?
C26 C21 C20 121.8(3) . . ?
C22 C21 C20 119.4(3) . . ?
O1 C13 O2 125.0(3) . 2_666 ?
O1 C13 C14 116.7(3) . . ?
O2 C13 C14 118.3(3) 2_666 . ?
C10 N2 C12 118.3(3) . . ?
C10 N2 Nd1 121.3(2) . . ?
C12 N2 Nd1 120.3(2) . . ?
C25 C26 C21 120.5(3) . . ?
O3 C20 O4 122.3(3) 2_666 . ?
O3 C20 C21 119.3(3) 2_666 . ?
O4 C20 C21 118.4(3) . . ?
N1 C11 C4 121.5(3) . . ?
N1 C11 C12 118.7(3) . . ?
C4 C11 C12 119.8(3) . . ?
C15 C14 C19 118.5(3) . . ?
C15 C14 C13 120.0(3) . . ?
C19 C14 C13 121.3(3) . . ?
C28 C29 C30 121.1(3) . . ?
N2 C12 C7 122.1(3) . . ?
N2 C12 C11 118.7(3) . . ?
C7 C12 C11 119.2(3) . . ?
O6 C27 O5 124.6(3) . . ?
O6 C27 C28 117.7(3) . . ?
O5 C27 C28 117.6(3) . . ?
C23 C22 C21 121.0(3) . . ?
C29 C28 C33 118.4(3) . . ?
C29 C28 C27 121.3(3) . . ?
C33 C28 C27 120.3(3) . . ?
C24 C25 C26 119.4(3) . . ?
C14 C15 C16 121.9(3) . . ?
C24 C23 C22 118.8(3) . . ?
N2 C10 C9 123.1(4) . . ?
C31 C30 C29 118.2(4) . . ?
C3 C2 C1 118.8(4) . . ?
N1 C1 C2 123.8(4) . . ?
C23 C24 C25 121.4(3) . . ?
C23 C24 Cl2 119.3(3) . . ?
C25 C24 Cl2 119.3(3) . . ?
C28 C33 C32 121.3(4) . . ?
C8 C7 C12 117.1(4) . . ?
C8 C7 C6 123.7(4) . . ?
C12 C7 C6 119.2(4) . . ?
C9 C8 C7 120.8(4) . . ?
C3 C4 C11 118.0(3) . . ?
C3 C4 C5 123.0(4) . . ?
C11 C4 C5 119.1(4) . . ?
C32 C31 C30 121.9(4) . . ?
C32 C31 Cl3 119.3(3) . . ?
C30 C31 Cl3 118.8(3) . . ?
C17 C16 C15 118.3(3) . . ?
C18 C19 C14 120.0(3) . . ?
C16 C17 C18 121.5(4) . . ?
C16 C17 Cl1 119.1(3) . . ?
C18 C17 Cl1 119.4(3) . . ?
C13 O2 Nd1 127.79(17) 2_666 . ?
C20 O3 Nd1 112.12(18) 2_666 . ?
C5 C6 C7 121.5(4) . . ?
C6 C5 C4 121.2(4) . . ?
C31 C32 C33 119.0(4) . . ?
C8 C9 C10 118.5(4) . . ?
C17 C18 C19 119.8(4) . . ?
C2 C3 C4 119.9(4) . . ?

_refine_diff_density_max         1.249
_refine_diff_density_min         -0.557
_refine_diff_density_rms         0.104

_shelxl_version_number           2013-4

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_h-m   'P -1'
_symmetry_int_tables_number      2
_chemical_absolute_configuration ?
_database_code_depnum_ccdc_archive 'CCDC 1018740'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_Compound_4



_audit_creation_method           SHELXL-2013
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C66 H40 Cl6 N4 O12 Sm2'
_chemical_melting_point          ?

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colorless

_diffrn_ambient_temperature      293(2)
_chemical_formula_weight         1594.42

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'
Cl Cl 0.1484 0.1585 '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'

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

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

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

_cell_length_a                   10.0492(4)
_cell_length_b                   11.9135(5)
_cell_length_c                   14.3855(6)
_cell_angle_alpha                110.397(2)
_cell_angle_beta                 96.364(3)
_cell_angle_gamma                102.190(2)
_cell_volume                     1545.56(11)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    22875
_cell_measurement_theta_min      4.709
_cell_measurement_theta_max      60.044
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.713
_exptl_crystal_F_000             786
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.14
_exptl_absorpt_coefficient_mu    2.208
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.5385
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   'SADABS, Bruker-AXS (2008)'

_exptl_special_details           
;
 ?
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22869
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.542
_diffrn_reflns_theta_max         30.311
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.915
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.915
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.915
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8502
_reflns_number_gt                7798
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX, Bruker-AXS'
_computing_cell_refinement       'SAINT, Bruker-AXS'
_computing_data_reduction        'SAINT, Bruker-AXS'
_computing_structure_solution    'SIR92 (Gualardi, 1994)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Crystal Maker (Palmer, 2009)'
_computing_publication_material  'WINGX (Farrugia, 2012)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0222P)²+0.5645P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8502
_refine_ls_number_parameters     406
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0247
_refine_ls_R_factor_gt           0.0213
_refine_ls_wR_factor_ref         0.0523
_refine_ls_wR_factor_gt          0.0503
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Sm1 Sm 0.37503(2) 0.12575(2) 0.06427(2) 0.02494(3) Uani 1 1 d . . . . .
Cl1 Cl 0.14367(9) 0.31647(8) 0.65981(5) 0.0716(2) Uani 1 1 d . . . . .
Cl2 Cl 1.18912(10) 0.58144(8) 0.41344(7) 0.0906(3) Uani 1 1 d . . . . .
Cl3 Cl 0.79483(12) 0.07891(10) 0.59388(6) 0.1005(3) Uani 1 1 d . . . . .
O4 O 0.61664(16) 0.16907(18) 0.09814(13) 0.0537(4) Uani 1 1 d . . . . .
O5 O 0.42336(16) -0.00566(14) 0.14827(11) 0.0422(3) Uani 1 1 d . . . . .
O2 O 0.42837(16) 0.26187(14) 0.25059(11) 0.0408(3) Uani 1 1 d . . . . .
O1 O 0.21251(15) 0.15300(14) 0.17607(10) 0.0379(3) Uani 1 1 d . . . . .
N2 N 0.40222(17) 0.35747(14) 0.08709(12) 0.0324(3) Uani 1 1 d . . . . .
O3 O 0.22484(16) -0.07292(13) -0.04257(12) 0.0441(4) Uani 1 1 d . . . . .
O6 O 0.42503(16) 0.11399(14) -0.09582(11) 0.0414(3) Uani 1 1 d . . . . .
C25 C 1.0871(2) 0.39654(19) 0.22941(19) 0.0428(5) Uani 1 1 d . . . . .
H25 H 1.1743 0.4191 0.2148 0.051 Uiso 1 1 calc R U . . .
N1 N 0.17024(16) 0.17824(14) -0.03524(11) 0.0286(3) Uani 1 1 d . . . . .
C20 C 0.7393(2) 0.16233(18) 0.10062(15) 0.0338(4) Uani 1 1 d . . . . .
C27 C 0.5245(2) -0.04729(17) 0.16389(14) 0.0311(4) Uani 1 1 d . . . . .
C11 C 0.3083(2) 0.39114(17) 0.03421(14) 0.0312(4) Uani 1 1 d . . . . .
C14 C 0.2633(2) 0.24878(19) 0.35662(15) 0.0370(4) Uani 1 1 d . . . . .
C12 C 0.1874(2) 0.29632(17) -0.03212(14) 0.0292(4) Uani 1 1 d . . . . .
C13 C 0.3044(2) 0.22056(18) 0.25533(15) 0.0333(4) Uani 1 1 d . . . . .
C28 C 0.5910(2) -0.01669(18) 0.27171(15) 0.0342(4) Uani 1 1 d . . . . .
C26 C 0.9825(2) 0.29857(18) 0.15876(15) 0.0342(4) Uani 1 1 d . . . . .
H26 H 1.0009 0.2526 0.0969 0.041 Uiso 1 1 calc R U . . .
C3 C -0.0305(2) 0.2364(2) -0.14806(18) 0.0469(5) Uani 1 1 d . . . . .
H3 H -0.0973 0.2547 -0.1863 0.056 Uiso 1 1 calc R U . . .
C21 C 0.85135(19) 0.26803(17) 0.17878(14) 0.0302(4) Uani 1 1 d . . . . .
C4 C 0.0892(2) 0.3294(2) -0.08826(16) 0.0374(4) Uani 1 1 d . . . . .
C22 C 0.8248(2) 0.3343(2) 0.27232(17) 0.0449(5) Uani 1 1 d . . . . .
H22 H 0.7365 0.3148 0.2862 0.054 Uiso 1 1 calc R U . . .
C18 C 0.3269(3) 0.3372(3) 0.53869(19) 0.0619(7) Uani 1 1 d . . . . .
H18 H 0.3937 0.3811 0.5980 0.074 Uiso 1 1 calc R U . . .
C17 C 0.1907(3) 0.2930(3) 0.54270(18) 0.0520(6) Uani 1 1 d . . . . .
C7 C 0.3233(2) 0.51548(19) 0.04364(17) 0.0408(5) Uani 1 1 d . . . . .
C16 C 0.0895(3) 0.2294(3) 0.45624(19) 0.0517(6) Uani 1 1 d . . . . .
H16 H -0.0026 0.2018 0.4603 0.062 Uiso 1 1 calc R U . . .
C19 C 0.3636(3) 0.3154(3) 0.44487(18) 0.0532(6) Uani 1 1 d . . . . .
H19 H 0.4553 0.3454 0.4411 0.064 Uiso 1 1 calc R U . . .
C5 C 0.1133(3) 0.4564(2) -0.0798(2) 0.0510(6) Uani 1 1 d . . . . .
H5 H 0.0507 0.4773 -0.1192 0.061 Uiso 1 1 calc R U . . .
C10 C 0.5105(2) 0.4468(2) 0.15165(17) 0.0437(5) Uani 1 1 d . . . . .
H10 H 0.5748 0.4247 0.1887 0.052 Uiso 1 1 calc R U . . .
C24 C 1.0584(3) 0.4599(2) 0.32210(19) 0.0494(6) Uani 1 1 d . . . . .
C33 C 0.7040(3) -0.0598(2) 0.29331(19) 0.0489(5) Uani 1 1 d . . . . .
H33 H 0.7377 -0.1094 0.2407 0.059 Uiso 1 1 calc R U . . .
C1 C 0.0547(2) 0.09351(19) -0.09303(15) 0.0357(4) Uani 1 1 d . . . . .
H1 H 0.0417 0.0127 -0.0958 0.043 Uiso 1 1 calc R U . . .
C29 C 0.5430(3) 0.0575(2) 0.35052(17) 0.0505(6) Uani 1 1 d . . . . .
H29 H 0.4676 0.0869 0.3367 0.061 Uiso 1 1 calc R U . . .
C32 C 0.7667(3) -0.0293(3) 0.3928(2) 0.0616(7) Uani 1 1 d . . . . .
H32 H 0.8423 -0.0582 0.4073 0.074 Uiso 1 1 calc R U . . .
C15 C 0.1271(3) 0.2069(2) 0.36274(17) 0.0447(5) Uani 1 1 d . . . . .
H15 H 0.0598 0.1632 0.3037 0.054 Uiso 1 1 calc R U . . .
C8 C 0.4397(3) 0.6059(2) 0.1125(2) 0.0543(6) Uani 1 1 d . . . . .
H8 H 0.4535 0.6889 0.1211 0.065 Uiso 1 1 calc R U . . .
C31 C 0.7164(3) 0.0438(3) 0.46936(19) 0.0594(7) Uani 1 1 d . . . . .
C6 C 0.2234(3) 0.5443(2) -0.0169(2) 0.0515(6) Uani 1 1 d . . . . .
H6 H 0.2357 0.6258 -0.0123 0.062 Uiso 1 1 calc R U . . .
C2 C -0.0489(2) 0.1189(2) -0.15013(17) 0.0454(5) Uani 1 1 d . . . . .
H2 H -0.1287 0.0566 -0.1887 0.054 Uiso 1 1 calc R U . . .
C9 C 0.5320(3) 0.5719(2) 0.1663(2) 0.0551(6) Uani 1 1 d . . . . .
H9 H 0.6087 0.6314 0.2125 0.066 Uiso 1 1 calc R U . . .
C23 C 0.9301(3) 0.4294(2) 0.34473(19) 0.0570(7) Uani 1 1 d . . . . .
H23 H 0.9140 0.4723 0.4083 0.068 Uiso 1 1 calc R U . . .
C30 C 0.6061(3) 0.0887(3) 0.45052(19) 0.0629(7) Uani 1 1 d . . . . .
H30 H 0.5740 0.1392 0.5036 0.075 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Sm1 O4 2.3307(15) . ?
Sm1 O6 2.3743(14) . ?
Sm1 O5 2.3783(14) . ?
Sm1 O3 2.3840(14) . ?
Sm1 O1 2.4086(14) . ?
Sm1 O2 2.5270(14) . ?
Sm1 N2 2.6140(15) . ?
Sm1 N1 2.6813(15) . ?
Sm1 C13 2.8179(19) . ?
Cl1 C17 1.744(2) . ?
Cl2 C24 1.743(2) . ?
Cl3 C31 1.741(2) . ?
O4 C20 1.249(2) . ?
O5 C27 1.253(2) . ?
O2 C13 1.258(3) . ?
O1 C13 1.270(2) . ?
N2 C10 1.333(3) . ?
N2 C11 1.358(2) . ?
O3 C20 1.253(3) 2_655 ?
O6 C27 1.259(2) 2_655 ?
C25 C24 1.381(4) . ?
C25 C26 1.385(3) . ?
N1 C1 1.328(2) . ?
N1 C12 1.365(2) . ?
C20 O3 1.253(3) 2_655 ?
C20 C21 1.501(3) . ?
C27 O6 1.259(2) 2_655 ?
C27 C28 1.503(3) . ?
C11 C7 1.413(3) . ?
C11 C12 1.441(3) . ?
C14 C15 1.378(3) . ?
C14 C19 1.391(3) . ?
C14 C13 1.503(3) . ?
C12 C4 1.411(3) . ?
C28 C29 1.379(3) . ?
C28 C33 1.390(3) . ?
C26 C21 1.381(3) . ?
C3 C2 1.362(3) . ?
C3 C4 1.399(3) . ?
C21 C22 1.391(3) . ?
C4 C5 1.439(3) . ?
C22 C23 1.384(3) . ?
C18 C17 1.375(4) . ?
C18 C19 1.390(3) . ?
C17 C16 1.376(4) . ?
C7 C8 1.407(3) . ?
C7 C6 1.430(3) . ?
C16 C15 1.388(3) . ?
C5 C6 1.330(4) . ?
C10 C9 1.396(3) . ?
C24 C23 1.370(4) . ?
C33 C32 1.385(3) . ?
C1 C2 1.402(3) . ?
C29 C30 1.391(3) . ?
C32 C31 1.367(4) . ?
C8 C9 1.357(4) . ?
C31 C30 1.369(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
O4 Sm1 O6 78.82(6) . . ?
O4 Sm1 O5 75.30(6) . . ?
O6 Sm1 O5 125.51(5) . . ?
O4 Sm1 O3 123.71(6) . . ?
O6 Sm1 O3 79.36(6) . . ?
O5 Sm1 O3 76.72(5) . . ?
O4 Sm1 O1 131.12(5) . . ?
O6 Sm1 O1 147.44(5) . . ?
O5 Sm1 O1 80.54(5) . . ?
O3 Sm1 O1 89.97(5) . . ?
O4 Sm1 O2 79.76(6) . . ?
O6 Sm1 O2 144.21(5) . . ?
O5 Sm1 O2 75.21(5) . . ?
O3 Sm1 O2 136.40(5) . . ?
O1 Sm1 O2 53.02(5) . . ?
O4 Sm1 N2 88.38(6) . . ?
O6 Sm1 N2 80.79(5) . . ?
O5 Sm1 N2 143.90(5) . . ?
O3 Sm1 N2 137.35(5) . . ?
O1 Sm1 N2 86.93(5) . . ?
O2 Sm1 N2 70.25(5) . . ?
O4 Sm1 N1 140.47(5) . . ?
O6 Sm1 N1 71.36(5) . . ?
O5 Sm1 N1 143.77(5) . . ?
O3 Sm1 N1 75.86(5) . . ?
O1 Sm1 N1 76.23(5) . . ?
O2 Sm1 N1 110.48(5) . . ?
N2 Sm1 N1 62.08(5) . . ?
O4 Sm1 C13 104.92(6) . . ?
O6 Sm1 C13 159.80(5) . . ?
O5 Sm1 C13 74.17(5) . . ?
O3 Sm1 C13 112.86(6) . . ?
O1 Sm1 C13 26.69(5) . . ?
O2 Sm1 C13 26.51(5) . . ?
N2 Sm1 C13 79.49(5) . . ?
N1 Sm1 C13 95.35(5) . . ?
C20 O4 Sm1 164.53(16) . . ?
C27 O5 Sm1 135.14(13) . . ?
C13 O2 Sm1 89.75(12) . . ?
C13 O1 Sm1 94.93(12) . . ?
C10 N2 C11 117.84(17) . . ?
C10 N2 Sm1 120.37(14) . . ?
C11 N2 Sm1 121.80(12) . . ?
C20 O3 Sm1 126.17(13) 2_655 . ?
C27 O6 Sm1 137.92(13) 2_655 . ?
C24 C25 C26 118.2(2) . . ?
C1 N1 C12 117.26(16) . . ?
C1 N1 Sm1 123.52(12) . . ?
C12 N1 Sm1 119.10(12) . . ?
O4 C20 O3 124.46(19) . 2_655 ?
O4 C20 C21 117.87(19) . . ?
O3 C20 C21 117.68(17) 2_655 . ?
O5 C27 O6 124.96(18) . 2_655 ?
O5 C27 C28 118.10(17) . . ?
O6 C27 C28 116.94(17) 2_655 . ?
N2 C11 C7 122.55(19) . . ?
N2 C11 C12 118.36(16) . . ?
C7 C11 C12 119.07(18) . . ?
C15 C14 C19 119.7(2) . . ?
C15 C14 C13 120.42(19) . . ?
C19 C14 C13 119.9(2) . . ?
N1 C12 C4 122.61(18) . . ?
N1 C12 C11 118.20(16) . . ?
C4 C12 C11 119.15(17) . . ?
O2 C13 O1 121.47(18) . . ?
O2 C13 C14 119.85(18) . . ?
O1 C13 C14 118.67(19) . . ?
O2 C13 Sm1 63.74(10) . . ?
O1 C13 Sm1 58.38(10) . . ?
C14 C13 Sm1 170.15(13) . . ?
C29 C28 C33 119.1(2) . . ?
C29 C28 C27 120.38(19) . . ?
C33 C28 C27 120.46(19) . . ?
C21 C26 C25 121.0(2) . . ?
C2 C3 C4 119.8(2) . . ?
C26 C21 C22 119.57(18) . . ?
C26 C21 C20 120.04(17) . . ?
C22 C21 C20 120.38(18) . . ?
C3 C4 C12 117.69(19) . . ?
C3 C4 C5 122.9(2) . . ?
C12 C4 C5 119.4(2) . . ?
C23 C22 C21 119.8(2) . . ?
C17 C18 C19 119.1(2) . . ?
C18 C17 C16 121.6(2) . . ?
C18 C17 Cl1 119.7(2) . . ?
C16 C17 Cl1 118.7(2) . . ?
C8 C7 C11 117.2(2) . . ?
C8 C7 C6 122.9(2) . . ?
C11 C7 C6 119.9(2) . . ?
C17 C16 C15 118.9(2) . . ?
C18 C19 C14 120.0(2) . . ?
C6 C5 C4 121.3(2) . . ?
N2 C10 C9 123.2(2) . . ?
C23 C24 C25 121.9(2) . . ?
C23 C24 Cl2 118.9(2) . . ?
C25 C24 Cl2 119.2(2) . . ?
C32 C33 C28 120.3(2) . . ?
N1 C1 C2 123.77(19) . . ?
C28 C29 C30 120.7(2) . . ?
C31 C32 C33 119.3(2) . . ?
C14 C15 C16 120.6(2) . . ?
C9 C8 C7 119.9(2) . . ?
C32 C31 C30 121.8(2) . . ?
C32 C31 Cl3 118.6(2) . . ?
C30 C31 Cl3 119.6(2) . . ?
C5 C6 C7 121.0(2) . . ?
C3 C2 C1 118.8(2) . . ?
C8 C9 C10 119.3(2) . . ?
C24 C23 C22 119.5(2) . . ?
C31 C30 C29 118.7(3) . . ?

_refine_diff_density_max         0.627
_refine_diff_density_min         -0.465
_refine_diff_density_rms         0.073

_shelxl_version_number           2013-4

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_h-m   'P -1'
_symmetry_int_tables_number      2
_chemical_absolute_configuration ?
_database_code_depnum_ccdc_archive 'CCDC 1018741'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_Compound_5


_audit_creation_method           SHELXL-2013
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C66 H40 Cl6 Gd2 N4 O12'
_chemical_melting_point          ?

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colorless

_diffrn_ambient_temperature      293(2)
_chemical_formula_weight         1608.22

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

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

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

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

_cell_length_a                   10.0755(3)
_cell_length_b                   11.8866(3)
_cell_length_c                   14.3488(4)
_cell_angle_alpha                110.75(3)
_cell_angle_beta                 96.41(3)
_cell_angle_gamma                101.87(2)
_cell_volume                     1540.3(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    23098
_cell_measurement_theta_min      4.704
_cell_measurement_theta_max      54.534
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.734
_exptl_crystal_F_000             790
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    2.462
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6855
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   'SADABS, Bruker-AXS (2008)'

_exptl_special_details           
;
 ?
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23098
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.549
_diffrn_reflns_theta_max         30.357
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.919
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.919
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.919
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8534
_reflns_number_gt                7505
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX, Bruker-AXS'
_computing_cell_refinement       'SAINT, Bruker-AXS'
_computing_data_reduction        'SAINT, Bruker-AXS'
_computing_structure_solution    'SIR92 (Gualardi, 1994)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Crystal Maker (Palmer, 2009)'
_computing_publication_material  'WINGX (Farrugia, 2012)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0246P)²+0.1107P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8534
_refine_ls_number_parameters     406
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0249
_refine_ls_wR_factor_ref         0.0539
_refine_ls_wR_factor_gt          0.0513
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Gd1 Gd 0.87592(2) 0.12696(2) 0.06455(2) 0.02595(4) Uani 1 1 d . . . . .
Cl1 Cl 0.64000(10) 0.31416(9) 0.65900(6) 0.0737(2) Uani 1 1 d . . . . .
Cl3 Cl 1.29154(13) 0.08031(11) 0.59558(7) 0.1069(4) Uani 1 1 d . . . . .
Cl2 Cl 1.68951(10) 0.58038(9) 0.41250(8) 0.0931(3) Uani 1 1 d . . . . .
O1 O 0.71298(17) 0.15180(16) 0.17418(12) 0.0396(4) Uani 1 1 d . . . . .
O2 O 0.92682(18) 0.26252(15) 0.25043(12) 0.0424(4) Uani 1 1 d . . . . .
O6 O 0.92618(18) -0.00264(16) 0.14746(12) 0.0438(4) Uani 1 1 d . . . . .
O4 O 1.11446(17) 0.17292(19) 0.09893(14) 0.0522(5) Uani 1 1 d . . . . .
N2 N 0.90471(19) 0.35679(16) 0.08755(14) 0.0333(4) Uani 1 1 d . . . . .
C25 C 1.5838(3) 0.3947(2) 0.2280(2) 0.0443(6) Uani 1 1 d . . . . .
H25 H 1.6704 0.4160 0.2126 0.053 Uiso 1 1 calc R U . . .
O5 O 0.92406(18) 0.11388(16) -0.09511(12) 0.0419(4) Uani 1 1 d . . . . .
O3 O 0.73119(18) -0.07119(14) -0.04234(13) 0.0439(4) Uani 1 1 d . . . . .
N1 N 0.67252(18) 0.17788(16) -0.03411(13) 0.0293(4) Uani 1 1 d . . . . .
C12 C 0.6891(2) 0.2961(2) -0.03076(16) 0.0300(4) Uani 1 1 d . . . . .
C20 C 1.2357(2) 0.1633(2) 0.10052(17) 0.0345(5) Uani 1 1 d . . . . .
C27 C 1.0261(2) -0.0461(2) 0.16317(17) 0.0324(5) Uani 1 1 d . . . . .
C14 C 0.7617(3) 0.2484(2) 0.35555(17) 0.0387(5) Uani 1 1 d . . . . .
C13 C 0.8030(3) 0.2204(2) 0.25448(17) 0.0341(5) Uani 1 1 d . . . . .
C11 C 0.8104(2) 0.3909(2) 0.03520(16) 0.0320(5) Uani 1 1 d . . . . .
C26 C 1.4787(2) 0.2969(2) 0.15689(18) 0.0356(5) Uani 1 1 d . . . . .
H26 H 1.4958 0.2505 0.0942 0.043 Uiso 1 1 calc R U . . .
C21 C 1.3491(2) 0.2679(2) 0.17842(16) 0.0313(5) Uani 1 1 d . . . . .
C7 C 0.8253(3) 0.5156(2) 0.04504(19) 0.0412(6) Uani 1 1 d . . . . .
C28 C 1.0906(2) -0.0152(2) 0.27192(17) 0.0352(5) Uani 1 1 d . . . . .
C4 C 0.5910(3) 0.3298(2) -0.08636(18) 0.0379(5) Uani 1 1 d . . . . .
C3 C 0.4715(3) 0.2363(3) -0.14587(19) 0.0476(6) Uani 1 1 d . . . . .
H3 H 0.4045 0.2546 -0.1841 0.057 Uiso 1 1 calc R U . . .
C5 C 0.6147(3) 0.4560(3) -0.0781(2) 0.0506(7) Uani 1 1 d . . . . .
H5 H 0.5521 0.4768 -0.1177 0.061 Uiso 1 1 calc R U . . .
C17 C 0.6879(3) 0.2918(3) 0.5419(2) 0.0529(7) Uani 1 1 d . . . . .
C10 C 1.0127(3) 0.4460(2) 0.15166(19) 0.0429(6) Uani 1 1 d . . . . .
H10 H 1.0775 0.4238 0.1882 0.052 Uiso 1 1 calc R U . . .
C22 C 1.3247(3) 0.3352(2) 0.27301(19) 0.0450(6) Uani 1 1 d . . . . .
H22 H 1.2372 0.3169 0.2878 0.054 Uiso 1 1 calc R U . . .
C1 C 0.5572(2) 0.0932(2) -0.09118(17) 0.0357(5) Uani 1 1 d . . . . .
H1 H 0.5446 0.0123 -0.0938 0.043 Uiso 1 1 calc R U . . .
C33 C 1.2023(3) -0.0595(3) 0.2937(2) 0.0495(6) Uani 1 1 d . . . . .
H33 H 1.2357 -0.1102 0.2410 0.059 Uiso 1 1 calc R U . . .
C16 C 0.5875(3) 0.2270(3) 0.4545(2) 0.0531(7) Uani 1 1 d . . . . .
H16 H 0.4958 0.1981 0.4580 0.064 Uiso 1 1 calc R U . . .
C19 C 0.8599(3) 0.3149(3) 0.4449(2) 0.0537(7) Uani 1 1 d . . . . .
H19 H 0.9514 0.3451 0.4418 0.064 Uiso 1 1 calc R U . . .
C24 C 1.5582(3) 0.4592(2) 0.3210(2) 0.0508(7) Uani 1 1 d . . . . .
C8 C 0.9412(3) 0.6055(2) 0.1135(2) 0.0539(7) Uani 1 1 d . . . . .
H8 H 0.9547 0.6887 0.1223 0.065 Uiso 1 1 calc R U . . .
C18 C 0.8232(3) 0.3367(3) 0.5387(2) 0.0647(9) Uani 1 1 d . . . . .
H18 H 0.8893 0.3811 0.5985 0.078 Uiso 1 1 calc R U . . .
C29 C 1.0422(3) 0.0593(3) 0.3507(2) 0.0534(7) Uani 1 1 d . . . . .
H29 H 0.9672 0.0892 0.3367 0.064 Uiso 1 1 calc R U . . .
C15 C 0.6260(3) 0.2059(2) 0.36150(19) 0.0457(6) Uani 1 1 d . . . . .
H15 H 0.5593 0.1622 0.3019 0.055 Uiso 1 1 calc R U . . .
C9 C 1.0337(3) 0.5716(2) 0.1669(2) 0.0538(7) Uani 1 1 d . . . . .
H9 H 1.1102 0.6312 0.2132 0.065 Uiso 1 1 calc R U . . .
C32 C 1.2643(3) -0.0282(3) 0.3940(2) 0.0652(9) Uani 1 1 d . . . . .
H32 H 1.3399 -0.0569 0.4088 0.078 Uiso 1 1 calc R U . . .
C23 C 1.4312(3) 0.4297(3) 0.3453(2) 0.0578(8) Uani 1 1 d . . . . .
H23 H 1.4167 0.4729 0.4097 0.069 Uiso 1 1 calc R U . . .
C2 C 0.4532(3) 0.1187(3) -0.14780(19) 0.0459(6) Uani 1 1 d . . . . .
H2 H 0.3733 0.0564 -0.1860 0.055 Uiso 1 1 calc R U . . .
C6 C 0.7247(3) 0.5448(2) -0.0149(2) 0.0522(7) Uani 1 1 d . . . . .
H6 H 0.7362 0.6266 -0.0098 0.063 Uiso 1 1 calc R U . . .
C31 C 1.2136(3) 0.0451(3) 0.4706(2) 0.0606(8) Uani 1 1 d . . . . .
C30 C 1.1043(4) 0.0903(3) 0.4510(2) 0.0662(9) Uani 1 1 d . . . . .
H30 H 1.0718 0.1411 0.5041 0.079 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Gd1 O4 2.3069(16) . ?
Gd1 O6 2.3516(16) . ?
Gd1 O5 2.3526(15) . ?
Gd1 O3 2.3567(16) . ?
Gd1 O1 2.3883(15) . ?
Gd1 O2 2.5063(16) . ?
Gd1 N2 2.5826(18) . ?
Gd1 N1 2.6534(17) . ?
Gd1 C13 2.800(2) . ?
Cl1 C17 1.745(3) . ?
Cl3 C31 1.739(3) . ?
Cl2 C24 1.743(3) . ?
O1 C13 1.270(3) . ?
O2 C13 1.261(3) . ?
O6 C27 1.256(3) . ?
O4 C20 1.249(3) . ?
N2 C10 1.329(3) . ?
N2 C11 1.359(3) . ?
C25 C24 1.367(4) . ?
C25 C26 1.388(3) . ?
C25 H25 0.9300 . ?
O5 C27 1.254(3) 2_755 ?
O3 C20 1.253(3) 2_755 ?
N1 C1 1.325(3) . ?
N1 C12 1.363(3) . ?
C12 C4 1.410(3) . ?
C12 C11 1.442(3) . ?
C20 O3 1.253(3) 2_755 ?
C20 C21 1.499(3) . ?
C27 O5 1.254(3) 2_755 ?
C27 C28 1.504(3) . ?
C14 C15 1.380(4) . ?
C14 C19 1.388(4) . ?
C14 C13 1.496(3) . ?
C11 C7 1.412(3) . ?
C26 C21 1.378(3) . ?
C26 H26 0.9300 . ?
C21 C22 1.389(3) . ?
C7 C8 1.398(4) . ?
C7 C6 1.431(4) . ?
C28 C29 1.376(3) . ?
C28 C33 1.387(3) . ?
C4 C3 1.400(4) . ?
C4 C5 1.429(3) . ?
C3 C2 1.363(4) . ?
C3 H3 0.9300 . ?
C5 C6 1.334(4) . ?
C5 H5 0.9300 . ?
C17 C18 1.370(4) . ?
C17 C16 1.379(4) . ?
C10 C9 1.396(3) . ?
C10 H10 0.9300 . ?
C22 C23 1.385(4) . ?
C22 H22 0.9300 . ?
C1 C2 1.401(3) . ?
C1 H1 0.9300 . ?
C33 C32 1.387(4) . ?
C33 H33 0.9300 . ?
C16 C15 1.383(4) . ?
C16 H16 0.9300 . ?
C19 C18 1.385(4) . ?
C19 H19 0.9300 . ?
C24 C23 1.372(4) . ?
C8 C9 1.354(4) . ?
C8 H8 0.9300 . ?
C18 H18 0.9300 . ?
C29 C30 1.387(4) . ?
C29 H29 0.9300 . ?
C15 H15 0.9300 . ?
C9 H9 0.9300 . ?
C32 C31 1.364(4) . ?
C32 H32 0.9300 . ?
C23 H23 0.9300 . ?
C2 H2 0.9300 . ?
C6 H6 0.9300 . ?
C31 C30 1.365(4) . ?
C30 H30 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 Gd1 O6 75.49(6) . . ?
O4 Gd1 O5 79.04(6) . . ?
O6 Gd1 O5 125.22(6) . . ?
O4 Gd1 O3 123.73(6) . . ?
O6 Gd1 O3 76.59(6) . . ?
O5 Gd1 O3 78.82(6) . . ?
O4 Gd1 O1 131.60(6) . . ?
O6 Gd1 O1 80.81(6) . . ?
O5 Gd1 O1 146.90(6) . . ?
O3 Gd1 O1 89.72(6) . . ?
O4 Gd1 O2 79.72(6) . . ?
O6 Gd1 O2 75.23(6) . . ?
O5 Gd1 O2 144.74(6) . . ?
O3 Gd1 O2 136.41(6) . . ?
O1 Gd1 O2 53.46(6) . . ?
O4 Gd1 N2 86.89(6) . . ?
O6 Gd1 N2 143.63(6) . . ?
O5 Gd1 N2 80.64(6) . . ?
O3 Gd1 N2 138.24(6) . . ?
O1 Gd1 N2 88.07(6) . . ?
O2 Gd1 N2 70.40(6) . . ?
O4 Gd1 N1 140.18(6) . . ?
O6 Gd1 N1 143.92(6) . . ?
O5 Gd1 N1 71.36(5) . . ?
O3 Gd1 N1 76.23(5) . . ?
O1 Gd1 N1 75.78(5) . . ?
O2 Gd1 N1 110.31(5) . . ?
N2 Gd1 N1 62.83(6) . . ?
O4 Gd1 C13 105.20(7) . . ?
O6 Gd1 C13 74.38(6) . . ?
O5 Gd1 C13 160.03(6) . . ?
O3 Gd1 C13 112.76(7) . . ?
O1 Gd1 C13 26.86(6) . . ?
O2 Gd1 C13 26.76(6) . . ?
N2 Gd1 C13 80.13(6) . . ?
N1 Gd1 C13 94.94(6) . . ?
C13 O1 Gd1 94.93(14) . . ?
C13 O2 Gd1 89.70(13) . . ?
C27 O6 Gd1 136.47(15) . . ?
C20 O4 Gd1 162.42(18) . . ?
C10 N2 C11 117.7(2) . . ?
C10 N2 Gd1 120.83(15) . . ?
C11 N2 Gd1 121.51(14) . . ?
C24 C25 C26 119.0(2) . . ?
C24 C25 H25 120.5 . . ?
C26 C25 H25 120.5 . . ?
C27 O5 Gd1 137.53(14) 2_755 . ?
C20 O3 Gd1 128.42(15) 2_755 . ?
C1 N1 C12 117.41(18) . . ?
C1 N1 Gd1 123.70(14) . . ?
C12 N1 Gd1 118.81(14) . . ?
N1 C12 C4 122.8(2) . . ?
N1 C12 C11 118.17(19) . . ?
C4 C12 C11 119.0(2) . . ?
O4 C20 O3 124.4(2) . 2_755 ?
O4 C20 C21 117.8(2) . . ?
O3 C20 C21 117.8(2) 2_755 . ?
O5 C27 O6 125.0(2) 2_755 . ?
O5 C27 C28 117.4(2) 2_755 . ?
O6 C27 C28 117.6(2) . . ?
C15 C14 C19 118.9(2) . . ?
C15 C14 C13 120.6(2) . . ?
C19 C14 C13 120.5(2) . . ?
O2 C13 O1 121.2(2) . . ?
O2 C13 C14 119.7(2) . . ?
O1 C13 C14 119.1(2) . . ?
O2 C13 Gd1 63.54(12) . . ?
O1 C13 Gd1 58.20(11) . . ?
C14 C13 Gd1 170.20(15) . . ?
N2 C11 C7 122.5(2) . . ?
N2 C11 C12 118.29(19) . . ?
C7 C11 C12 119.2(2) . . ?
C21 C26 C25 120.5(2) . . ?
C21 C26 H26 119.7 . . ?
C25 C26 H26 119.7 . . ?
C26 C21 C22 119.7(2) . . ?
C26 C21 C20 120.1(2) . . ?
C22 C21 C20 120.3(2) . . ?
C8 C7 C11 117.3(2) . . ?
C8 C7 C6 123.0(2) . . ?
C11 C7 C6 119.8(2) . . ?
C29 C28 C33 119.3(2) . . ?
C29 C28 C27 120.7(2) . . ?
C33 C28 C27 120.0(2) . . ?
C3 C4 C12 117.3(2) . . ?
C3 C4 C5 123.0(2) . . ?
C12 C4 C5 119.7(2) . . ?
C2 C3 C4 120.0(2) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C6 C5 C4 121.5(2) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C18 C17 C16 121.8(2) . . ?
C18 C17 Cl1 119.7(2) . . ?
C16 C17 Cl1 118.4(2) . . ?
N2 C10 C9 123.3(2) . . ?
N2 C10 H10 118.4 . . ?
C9 C10 H10 118.4 . . ?
C23 C22 C21 119.7(2) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
N1 C1 C2 123.7(2) . . ?
N1 C1 H1 118.2 . . ?
C2 C1 H1 118.2 . . ?
C28 C33 C32 120.0(3) . . ?
C28 C33 H33 120.0 . . ?
C32 C33 H33 120.0 . . ?
C17 C16 C15 118.5(3) . . ?
C17 C16 H16 120.7 . . ?
C15 C16 H16 120.7 . . ?
C18 C19 C14 120.7(3) . . ?
C18 C19 H19 119.6 . . ?
C14 C19 H19 119.6 . . ?
C25 C24 C23 121.5(2) . . ?
C25 C24 Cl2 119.9(2) . . ?
C23 C24 Cl2 118.6(2) . . ?
C9 C8 C7 120.1(2) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C17 C18 C19 118.9(3) . . ?
C17 C18 H18 120.6 . . ?
C19 C18 H18 120.6 . . ?
C28 C29 C30 120.6(3) . . ?
C28 C29 H29 119.7 . . ?
C30 C29 H29 119.7 . . ?
C14 C15 C16 121.1(3) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C8 C9 C10 119.1(2) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
C31 C32 C33 119.5(3) . . ?
C31 C32 H32 120.2 . . ?
C33 C32 H32 120.2 . . ?
C24 C23 C22 119.5(3) . . ?
C24 C23 H23 120.2 . . ?
C22 C23 H23 120.2 . . ?
C3 C2 C1 118.7(2) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C5 C6 C7 120.8(2) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C32 C31 C30 121.5(3) . . ?
C32 C31 Cl3 118.4(2) . . ?
C30 C31 Cl3 120.1(3) . . ?
C31 C30 C29 119.1(3) . . ?
C31 C30 H30 120.4 . . ?
C29 C30 H30 120.4 . . ?

_refine_diff_density_max         0.528
_refine_diff_density_min         -0.487
_refine_diff_density_rms         0.077

_shelxl_version_number           2013-4

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_h-m   'P -1'
_symmetry_int_tables_number      2
_chemical_absolute_configuration ?
_database_code_depnum_ccdc_archive 'CCDC 1018742'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_Compound_6


_audit_creation_method           SHELXL-2013
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C66 H40 Cl6 Ho2 N4 O12'
_chemical_melting_point          ?

_exptl_crystal_description       Plate
_exptl_crystal_colour            Pink

_diffrn_ambient_temperature      293(2)
_chemical_formula_weight         1623.58

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'
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'
Cl Cl 0.1484 0.1585 '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'

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

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

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

_cell_length_a                   10.0939(3)
_cell_length_b                   11.8412(4)
_cell_length_c                   14.2899(5)
_cell_angle_alpha                111.041(2)
_cell_angle_beta                 96.4820(10)
_cell_angle_gamma                101.4680(10)
_cell_volume                     1530.24(9)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    22815
_cell_measurement_theta_min      4.702
_cell_measurement_theta_max      52.753
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.762
_exptl_crystal_F_000             796
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    2.896
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6432
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   'SADABS, Bruker-AXS (2008)'

_exptl_special_details           
;
 ?
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22815
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.559
_diffrn_reflns_theta_max         30.122
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.932
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.932
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.932
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8415
_reflns_number_gt                7359
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX, Bruker-AXS'
_computing_cell_refinement       'SAINT, Bruker-AXS'
_computing_data_reduction        'SAINT, Bruker-AXS'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Crystal Maker (Palmer, 2009)'
_computing_publication_material  'WINGX (Farrugia, 2012)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0239P)²+0.1125P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8415
_refine_ls_number_parameters     406
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0258
_refine_ls_wR_factor_ref         0.0541
_refine_ls_wR_factor_gt          0.0512
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ho1 Ho 0.87697(2) 0.12789(2) 0.06470(2) 0.02550(4) Uani 1 1 d . . . . .
Cl1 Cl 0.63753(10) 0.31295(10) 0.65843(6) 0.0720(3) Uani 1 1 d . . . . .
Cl3 Cl 0.31103(11) -0.57849(9) -0.41061(8) 0.0881(3) Uani 1 1 d . . . . .
Cl2 Cl 0.71054(14) -0.08141(12) -0.59689(7) 0.1045(4) Uani 1 1 d . . . . .
N1 N 0.67510(19) 0.17669(17) -0.03292(14) 0.0281(4) Uani 1 1 d . . . . .
N2 N 0.9069(2) 0.35502(18) 0.08760(15) 0.0321(4) Uani 1 1 d . . . . .
O1 O 0.71501(18) 0.15047(17) 0.17146(13) 0.0379(4) Uani 1 1 d . . . . .
O2 O 0.92701(19) 0.26239(16) 0.24962(13) 0.0410(4) Uani 1 1 d . . . . .
O3 O 0.92394(19) 0.11352(17) -0.09320(13) 0.0410(4) Uani 1 1 d . . . . .
O6 O 0.73826(18) -0.06816(15) -0.04132(14) 0.0413(4) Uani 1 1 d . . . . .
O5 O 0.9274(2) -0.00015(17) 0.14619(14) 0.0434(4) Uani 1 1 d . . . . .
C20 C 0.9742(3) 0.0450(2) -0.16185(19) 0.0315(5) Uani 1 1 d . . . . .
C12 C 0.6913(2) 0.2950(2) -0.02977(18) 0.0298(5) Uani 1 1 d . . . . .
O4 O 1.11114(18) 0.17572(19) 0.09954(15) 0.0487(5) Uani 1 1 d . . . . .
C11 C 0.8123(3) 0.3897(2) 0.03612(18) 0.0308(5) Uani 1 1 d . . . . .
C28 C 0.6546(2) -0.2663(2) -0.17736(18) 0.0300(5) Uani 1 1 d . . . . .
C27 C 0.7688(2) -0.1622(2) -0.10011(18) 0.0320(5) Uani 1 1 d . . . . .
C29 C 0.5260(3) -0.2943(2) -0.1544(2) 0.0351(5) Uani 1 1 d . . . . .
H29 H 0.5100 -0.2474 -0.0908 0.042 Uiso 1 1 calc R U . . .
C31 C 0.4443(3) -0.4572(3) -0.3205(2) 0.0491(7) Uani 1 1 d . . . . .
C13 C 0.8041(3) 0.2199(2) 0.25276(19) 0.0346(6) Uani 1 1 d . . . . .
C17 C 0.6866(3) 0.2912(3) 0.5412(2) 0.0514(8) Uani 1 1 d . . . . .
C21 C 0.9095(3) 0.0151(2) -0.27092(19) 0.0343(5) Uani 1 1 d . . . . .
C4 C 0.5924(3) 0.3287(3) -0.08517(19) 0.0371(6) Uani 1 1 d . . . . .
C14 C 0.7607(3) 0.2477(2) 0.35440(19) 0.0366(6) Uani 1 1 d . . . . .
C7 C 0.8266(3) 0.5152(2) 0.0461(2) 0.0398(6) Uani 1 1 d . . . . .
C10 C 1.0151(3) 0.4445(2) 0.1518(2) 0.0415(6) Uani 1 1 d . . . . .
H10 H 1.0800 0.4219 0.1882 0.050 Uiso 1 1 calc R U . . .
C1 C 0.5597(3) 0.0921(2) -0.08964(19) 0.0359(6) Uani 1 1 d . . . . .
H1 H 0.5472 0.0111 -0.0921 0.043 Uiso 1 1 calc R U . . .
C6 C 0.7259(3) 0.5443(3) -0.0133(2) 0.0492(7) Uani 1 1 d . . . . .
H6 H 0.7372 0.6265 -0.0079 0.059 Uiso 1 1 calc R U . . .
C3 C 0.4728(3) 0.2359(3) -0.1446(2) 0.0457(7) Uani 1 1 d . . . . .
H3 H 0.4056 0.2542 -0.1827 0.055 Uiso 1 1 calc R U . . .
C33 C 0.6772(3) -0.3346(3) -0.2733(2) 0.0453(7) Uani 1 1 d . . . . .
H33 H 0.7640 -0.3170 -0.2889 0.054 Uiso 1 1 calc R U . . .
C2 C 0.4559(3) 0.1177(3) -0.1459(2) 0.0450(7) Uani 1 1 d . . . . .
H2 H 0.3762 0.0553 -0.1838 0.054 Uiso 1 1 calc R U . . .
C22 C 0.7976(3) 0.0592(3) -0.2930(2) 0.0487(7) Uani 1 1 d . . . . .
H22 H 0.7636 0.1099 -0.2400 0.058 Uiso 1 1 calc R U . . .
C5 C 0.6156(3) 0.4560(3) -0.0766(2) 0.0494(7) Uani 1 1 d . . . . .
H5 H 0.5527 0.4772 -0.1158 0.059 Uiso 1 1 calc R U . . .
C18 C 0.8208(4) 0.3363(4) 0.5387(2) 0.0653(9) Uani 1 1 d . . . . .
H18 H 0.8862 0.3805 0.5991 0.078 Uiso 1 1 calc R U . . .
C32 C 0.5701(3) -0.4292(3) -0.3456(2) 0.0562(8) Uani 1 1 d . . . . .
H32 H 0.5838 -0.4732 -0.4107 0.067 Uiso 1 1 calc R U . . .
C30 C 0.4201(3) -0.3921(2) -0.2255(2) 0.0429(6) Uani 1 1 d . . . . .
H30 H 0.3345 -0.4132 -0.2091 0.051 Uiso 1 1 calc R U . . .
C19 C 0.8587(3) 0.3153(3) 0.4444(2) 0.0524(8) Uani 1 1 d . . . . .
H19 H 0.9496 0.3465 0.4417 0.063 Uiso 1 1 calc R U . . .
C15 C 0.6260(3) 0.2045(3) 0.3592(2) 0.0454(7) Uani 1 1 d . . . . .
H15 H 0.5602 0.1604 0.2990 0.055 Uiso 1 1 calc R U . . .
C9 C 1.0361(3) 0.5699(3) 0.1671(2) 0.0518(7) Uani 1 1 d . . . . .
H9 H 1.1132 0.6292 0.2130 0.062 Uiso 1 1 calc R U . . .
C26 C 0.9581(3) -0.0599(3) -0.3505(2) 0.0536(8) Uani 1 1 d . . . . .
H26 H 1.0329 -0.0902 -0.3364 0.064 Uiso 1 1 calc R U . . .
C16 C 0.5868(3) 0.2261(3) 0.4528(2) 0.0522(8) Uani 1 1 d . . . . .
H16 H 0.4954 0.1973 0.4560 0.063 Uiso 1 1 calc R U . . .
C24 C 0.7872(4) -0.0454(3) -0.4708(2) 0.0594(9) Uani 1 1 d . . . . .
C8 C 0.9429(3) 0.6052(3) 0.1143(2) 0.0522(8) Uani 1 1 d . . . . .
H8 H 0.9564 0.6888 0.1235 0.063 Uiso 1 1 calc R U . . .
C23 C 0.7361(4) 0.0278(3) -0.3937(3) 0.0625(9) Uani 1 1 d . . . . .
H23 H 0.6603 0.0567 -0.4086 0.075 Uiso 1 1 calc R U . . .
C25 C 0.8969(4) -0.0910(3) -0.4514(2) 0.0672(10) Uani 1 1 d . . . . .
H25 H 0.9298 -0.1420 -0.5049 0.081 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ho1 O4 2.2705(17) . ?
Ho1 O3 2.3115(17) . ?
Ho1 O6 2.3125(16) . ?
Ho1 O5 2.3141(17) . ?
Ho1 O1 2.3484(17) . ?
Ho1 O2 2.4761(17) . ?
Ho1 N2 2.5405(19) . ?
Ho1 N1 2.6148(18) . ?
Ho1 C13 2.759(2) . ?
Cl1 C17 1.745(3) . ?
Cl3 C31 1.745(3) . ?
Cl2 C24 1.740(3) . ?
N1 C1 1.325(3) . ?
N1 C12 1.362(3) . ?
N2 C10 1.331(3) . ?
N2 C11 1.356(3) . ?
O1 C13 1.272(3) . ?
O2 C13 1.255(3) . ?
O3 C20 1.258(3) . ?
O6 C27 1.251(3) . ?
O5 C20 1.250(3) 2_755 ?
C20 O5 1.250(3) 2_755 ?
C20 C21 1.504(3) . ?
C12 C4 1.410(3) . ?
C12 C11 1.440(3) . ?
O4 C27 1.253(3) 2_755 ?
C11 C7 1.416(3) . ?
C28 C29 1.381(3) . ?
C28 C33 1.390(3) . ?
C28 C27 1.496(3) . ?
C27 O4 1.253(3) 2_755 ?
C29 C30 1.390(4) . ?
C29 H29 0.9300 . ?
C31 C32 1.368(4) . ?
C31 C30 1.377(4) . ?
C13 C14 1.506(3) . ?
C17 C18 1.364(5) . ?
C17 C16 1.382(4) . ?
C21 C26 1.378(4) . ?
C21 C22 1.386(4) . ?
C4 C3 1.399(4) . ?
C4 C5 1.435(4) . ?
C14 C15 1.373(4) . ?
C14 C19 1.390(4) . ?
C7 C8 1.401(4) . ?
C7 C6 1.424(4) . ?
C10 C9 1.389(4) . ?
C10 H10 0.9300 . ?
C1 C2 1.395(4) . ?
C1 H1 0.9300 . ?
C6 C5 1.335(4) . ?
C6 H6 0.9300 . ?
C3 C2 1.368(4) . ?
C3 H3 0.9300 . ?
C33 C32 1.388(4) . ?
C33 H33 0.9300 . ?
C2 H2 0.9300 . ?
C22 C23 1.385(4) . ?
C22 H22 0.9300 . ?
C5 H5 0.9300 . ?
C18 C19 1.391(4) . ?
C18 H18 0.9300 . ?
C32 H32 0.9300 . ?
C30 H30 0.9300 . ?
C19 H19 0.9300 . ?
C15 C16 1.388(4) . ?
C15 H15 0.9300 . ?
C9 C8 1.360(4) . ?
C9 H9 0.9300 . ?
C26 C25 1.386(4) . ?
C26 H26 0.9300 . ?
C16 H16 0.9300 . ?
C24 C23 1.361(5) . ?
C24 C25 1.368(5) . ?
C8 H8 0.9300 . ?
C23 H23 0.9300 . ?
C25 H25 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 Ho1 O3 79.10(7) . . ?
O4 Ho1 O6 123.84(7) . . ?
O3 Ho1 O6 78.43(7) . . ?
O4 Ho1 O5 75.96(7) . . ?
O3 Ho1 O5 124.86(6) . . ?
O6 Ho1 O5 76.24(6) . . ?
O4 Ho1 O1 132.00(6) . . ?
O3 Ho1 O1 146.59(6) . . ?
O6 Ho1 O1 89.42(7) . . ?
O5 Ho1 O1 80.84(6) . . ?
O4 Ho1 O2 79.23(7) . . ?
O3 Ho1 O2 144.99(6) . . ?
O6 Ho1 O2 136.57(6) . . ?
O5 Ho1 O2 75.19(6) . . ?
O1 Ho1 O2 54.26(6) . . ?
O4 Ho1 N2 85.51(7) . . ?
O3 Ho1 N2 80.57(6) . . ?
O6 Ho1 N2 139.02(6) . . ?
O5 Ho1 N2 143.55(6) . . ?
O1 Ho1 N2 89.17(6) . . ?
O2 Ho1 N2 70.62(6) . . ?
O4 Ho1 N1 140.16(7) . . ?
O3 Ho1 N1 71.69(6) . . ?
O6 Ho1 N1 76.34(6) . . ?
O5 Ho1 N1 143.50(7) . . ?
O1 Ho1 N1 75.24(6) . . ?
O2 Ho1 N1 110.53(6) . . ?
N2 Ho1 N1 63.75(6) . . ?
O4 Ho1 C13 105.08(8) . . ?
O3 Ho1 C13 160.44(7) . . ?
O6 Ho1 C13 112.84(7) . . ?
O5 Ho1 C13 74.38(7) . . ?
O1 Ho1 C13 27.37(7) . . ?
O2 Ho1 C13 27.05(7) . . ?
N2 Ho1 C13 80.73(7) . . ?
N1 Ho1 C13 94.80(7) . . ?
C1 N1 C12 117.3(2) . . ?
C1 N1 Ho1 124.24(16) . . ?
C12 N1 Ho1 118.36(15) . . ?
C10 N2 C11 117.6(2) . . ?
C10 N2 Ho1 121.19(17) . . ?
C11 N2 Ho1 121.21(15) . . ?
C13 O1 Ho1 94.59(15) . . ?
C13 O2 Ho1 89.14(15) . . ?
C20 O3 Ho1 137.68(16) . . ?
C27 O6 Ho1 130.35(16) . . ?
C20 O5 Ho1 137.26(17) 2_755 . ?
O5 C20 O3 125.1(2) 2_755 . ?
O5 C20 C21 118.1(2) 2_755 . ?
O3 C20 C21 116.8(2) . . ?
N1 C12 C4 122.7(2) . . ?
N1 C12 C11 118.0(2) . . ?
C4 C12 C11 119.2(2) . . ?
C27 O4 Ho1 159.99(19) 2_755 . ?
N2 C11 C7 122.7(2) . . ?
N2 C11 C12 118.3(2) . . ?
C7 C11 C12 119.0(2) . . ?
C29 C28 C33 119.6(2) . . ?
C29 C28 C27 120.3(2) . . ?
C33 C28 C27 120.0(2) . . ?
O6 C27 O4 124.7(2) . 2_755 ?
O6 C27 C28 118.1(2) . . ?
O4 C27 C28 117.2(2) 2_755 . ?
C28 C29 C30 120.5(2) . . ?
C28 C29 H29 119.8 . . ?
C30 C29 H29 119.8 . . ?
C32 C31 C30 121.6(3) . . ?
C32 C31 Cl3 119.4(2) . . ?
C30 C31 Cl3 119.0(2) . . ?
O2 C13 O1 121.3(2) . . ?
O2 C13 C14 119.9(2) . . ?
O1 C13 C14 118.7(2) . . ?
O2 C13 Ho1 63.81(13) . . ?
O1 C13 Ho1 58.04(12) . . ?
C14 C13 Ho1 170.22(17) . . ?
C18 C17 C16 121.9(3) . . ?
C18 C17 Cl1 119.9(2) . . ?
C16 C17 Cl1 118.2(2) . . ?
C26 C21 C22 119.0(3) . . ?
C26 C21 C20 120.3(2) . . ?
C22 C21 C20 120.6(2) . . ?
C3 C4 C12 117.8(2) . . ?
C3 C4 C5 122.7(2) . . ?
C12 C4 C5 119.5(3) . . ?
C15 C14 C19 119.6(3) . . ?
C15 C14 C13 120.7(2) . . ?
C19 C14 C13 119.7(2) . . ?
C8 C7 C11 117.1(2) . . ?
C8 C7 C6 123.1(3) . . ?
C11 C7 C6 119.7(3) . . ?
N2 C10 C9 123.4(3) . . ?
N2 C10 H10 118.3 . . ?
C9 C10 H10 118.3 . . ?
N1 C1 C2 123.7(2) . . ?
N1 C1 H1 118.1 . . ?
C2 C1 H1 118.1 . . ?
C5 C6 C7 121.2(3) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C2 C3 C4 119.2(2) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C32 C33 C28 119.9(3) . . ?
C32 C33 H33 120.1 . . ?
C28 C33 H33 120.1 . . ?
C3 C2 C1 119.2(3) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C23 C22 C21 120.2(3) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C6 C5 C4 121.2(3) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C17 C18 C19 119.1(3) . . ?
C17 C18 H18 120.5 . . ?
C19 C18 H18 120.5 . . ?
C31 C32 C33 119.5(3) . . ?
C31 C32 H32 120.2 . . ?
C33 C32 H32 120.2 . . ?
C31 C30 C29 118.8(3) . . ?
C31 C30 H30 120.6 . . ?
C29 C30 H30 120.6 . . ?
C14 C19 C18 120.1(3) . . ?
C14 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C14 C15 C16 120.8(3) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C8 C9 C10 119.3(3) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
C21 C26 C25 120.9(3) . . ?
C21 C26 H26 119.5 . . ?
C25 C26 H26 119.5 . . ?
C17 C16 C15 118.5(3) . . ?
C17 C16 H16 120.7 . . ?
C15 C16 H16 120.7 . . ?
C23 C24 C25 121.6(3) . . ?
C23 C24 Cl2 118.9(3) . . ?
C25 C24 Cl2 119.5(3) . . ?
C9 C8 C7 119.8(3) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C24 C23 C22 119.6(3) . . ?
C24 C23 H23 120.2 . . ?
C22 C23 H23 120.2 . . ?
C24 C25 C26 118.8(3) . . ?
C24 C25 H25 120.6 . . ?
C26 C25 H25 120.6 . . ?

_refine_diff_density_max         0.500
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.086

_shelxl_version_number           2013-4

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_h-m   'P -1'
_symmetry_int_tables_number      2
_chemical_absolute_configuration ?
_database_code_depnum_ccdc_archive 'CCDC 1018743'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_Compound_7


_audit_creation_method           SHELXL-2013
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C66 H40 Cl6 Er2 N4 O12'
_chemical_melting_point          ?

_exptl_crystal_description       Plate
_exptl_crystal_colour            Pink

_diffrn_ambient_temperature      293(2)
_chemical_formula_weight         1628.24

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

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

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

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

_cell_length_a                   10.0959(3)
_cell_length_b                   11.8279(3)
_cell_length_c                   14.2740(4)
_cell_angle_alpha                111.1860(9)
_cell_angle_beta                 96.4610(9)
_cell_angle_gamma                101.3860(11)
_cell_volume                     1526.17(7)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    22343
_cell_measurement_theta_min      4.705
_cell_measurement_theta_max      54.239
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.772
_exptl_crystal_F_000             798
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    3.061
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6712
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   'SADABS, Bruker-AXS (2008)'

_exptl_special_details           
;
 ?
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22340
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.562
_diffrn_reflns_theta_max         29.078
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8051
_reflns_number_gt                7147
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX, Bruker-AXS'
_computing_cell_refinement       'SAINT, Bruker-AXS'
_computing_data_reduction        'SAINT, Bruker-AXS'
_computing_structure_solution    'SIR92 (Gualardi, 1994)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Crystal Maker (Palmer, 2009)'
_computing_publication_material  'WINGX (Farrugia, 2012)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0235P)²+0.1126P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8051
_refine_ls_number_parameters     406
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0236
_refine_ls_wR_factor_ref         0.0515
_refine_ls_wR_factor_gt          0.0493
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Er1 Er 0.37734(2) 0.12828(2) 0.06478(2) 0.02436(4) Uani 1 1 d . . . . .
Cl1 Cl 0.13616(10) 0.31224(10) 0.65828(6) 0.0691(2) Uani 1 1 d . . . . .
Cl2 Cl -0.18916(10) -0.57832(9) -0.41018(8) 0.0840(3) Uani 1 1 d . . . . .
Cl3 Cl 0.78847(13) 0.08169(11) 0.59744(7) 0.1016(4) Uani 1 1 d . . . . .
C25 C -0.0796(3) -0.3918(2) -0.2247(2) 0.0402(6) Uani 1 1 d . . . . .
H25 H -0.1649 -0.4126 -0.2079 0.048 Uiso 1 1 calc R U . . .
O1 O 0.21552(18) 0.15016(17) 0.17053(13) 0.0369(4) Uani 1 1 d . . . . .
O2 O 0.42687(19) 0.26264(16) 0.24946(13) 0.0394(4) Uani 1 1 d . . . . .
O5 O 0.42783(19) 0.00093(17) 0.14592(13) 0.0414(4) Uani 1 1 d . . . . .
O6 O 0.42361(18) 0.11336(17) -0.09275(13) 0.0392(4) Uani 1 1 d . . . . .
O3 O 0.23980(18) -0.06742(16) -0.04133(14) 0.0398(4) Uani 1 1 d . . . . .
N2 N 0.4075(2) 0.35471(18) 0.08786(15) 0.0301(4) Uani 1 1 d . . . . .
O4 O 0.61021(17) 0.17672(19) 0.09938(14) 0.0460(5) Uani 1 1 d . . . . .
C12 C 0.1915(2) 0.2945(2) -0.02928(17) 0.0280(5) Uani 1 1 d . . . . .
N1 N 0.17570(19) 0.17615(17) -0.03266(14) 0.0282(4) Uani 1 1 d . . . . .
C20 C 0.2702(2) -0.1624(2) -0.09970(18) 0.0309(5) Uani 1 1 d . . . . .
C13 C 0.3039(3) 0.2202(2) 0.25271(19) 0.0330(5) Uani 1 1 d . . . . .
C27 C 0.5260(2) -0.0445(2) 0.16146(18) 0.0304(5) Uani 1 1 d . . . . .
C11 C 0.3131(2) 0.3894(2) 0.03602(17) 0.0287(5) Uani 1 1 d . . . . .
C21 C 0.1552(2) -0.2666(2) -0.17713(18) 0.0293(5) Uani 1 1 d . . . . .
C14 C 0.2608(3) 0.2478(2) 0.35387(19) 0.0354(6) Uani 1 1 d . . . . .
C28 C 0.5899(3) -0.0149(2) 0.27071(18) 0.0330(5) Uani 1 1 d . . . . .
C1 C 0.0599(2) 0.0913(2) -0.08939(19) 0.0350(5) Uani 1 1 d . . . . .
H1 H 0.0475 0.0102 -0.0919 0.042 Uiso 1 1 calc R U . . .
C7 C 0.3276(3) 0.5154(2) 0.0466(2) 0.0373(6) Uani 1 1 d . . . . .
C5 C 0.1163(3) 0.4558(3) -0.0760(2) 0.0464(7) Uani 1 1 d . . . . .
H5 H 0.0531 0.4769 -0.1151 0.056 Uiso 1 1 calc R U . . .
C4 C 0.0929(3) 0.3284(2) -0.08456(19) 0.0346(5) Uani 1 1 d . . . . .
C29 C 0.7020(3) -0.0589(3) 0.2928(2) 0.0471(7) Uani 1 1 d . . . . .
H29 H 0.7365 -0.1091 0.2397 0.057 Uiso 1 1 calc R U . . .
C17 C 0.1848(3) 0.2902(3) 0.5409(2) 0.0496(7) Uani 1 1 d . . . . .
C10 C 0.5160(3) 0.4440(2) 0.1522(2) 0.0395(6) Uani 1 1 d . . . . .
H10 H 0.5810 0.4212 0.1884 0.047 Uiso 1 1 calc R U . . .
C24 C -0.0560(3) -0.4574(3) -0.3201(2) 0.0461(7) Uani 1 1 d . . . . .
C26 C 0.0270(2) -0.2936(2) -0.15381(19) 0.0341(5) Uani 1 1 d . . . . .
H26 H 0.0114 -0.2458 -0.0902 0.041 Uiso 1 1 calc R U . . .
C33 C 0.5408(3) 0.0606(3) 0.3506(2) 0.0511(8) Uani 1 1 d . . . . .
H33 H 0.4660 0.0911 0.3367 0.061 Uiso 1 1 calc R U . . .
C18 C 0.3193(4) 0.3356(3) 0.5387(2) 0.0585(9) Uani 1 1 d . . . . .
H18 H 0.3843 0.3794 0.5995 0.070 Uiso 1 1 calc R U . . .
C3 C -0.0264(3) 0.2353(3) -0.1437(2) 0.0437(7) Uani 1 1 d . . . . .
H3 H -0.0935 0.2538 -0.1818 0.052 Uiso 1 1 calc R U . . .
C8 C 0.4438(3) 0.6056(3) 0.1150(2) 0.0492(7) Uani 1 1 d . . . . .
H8 H 0.4572 0.6894 0.1244 0.059 Uiso 1 1 calc R U . . .
C9 C 0.5367(3) 0.5701(3) 0.1676(2) 0.0490(7) Uani 1 1 d . . . . .
H9 H 0.6137 0.6295 0.2136 0.059 Uiso 1 1 calc R U . . .
C15 C 0.1256(3) 0.2044(3) 0.3589(2) 0.0436(6) Uani 1 1 d . . . . .
H15 H 0.0600 0.1603 0.2985 0.052 Uiso 1 1 calc R U . . .
C2 C -0.0441(3) 0.1170(3) -0.1454(2) 0.0429(6) Uani 1 1 d . . . . .
H2 H -0.1240 0.0547 -0.1833 0.051 Uiso 1 1 calc R U . . .
C19 C 0.3583(3) 0.3156(3) 0.4445(2) 0.0510(7) Uani 1 1 d . . . . .
H19 H 0.4492 0.3475 0.4423 0.061 Uiso 1 1 calc R U . . .
C16 C 0.0860(3) 0.2252(3) 0.4518(2) 0.0497(7) Uani 1 1 d . . . . .
H16 H -0.0055 0.1961 0.4545 0.060 Uiso 1 1 calc R U . . .
C22 C 0.1766(3) -0.3348(3) -0.2736(2) 0.0419(6) Uani 1 1 d . . . . .
H22 H 0.2628 -0.3168 -0.2899 0.050 Uiso 1 1 calc R U . . .
C32 C 0.6026(4) 0.0912(3) 0.4516(2) 0.0640(9) Uani 1 1 d . . . . .
H32 H 0.5695 0.1420 0.5054 0.077 Uiso 1 1 calc R U . . .
C23 C 0.0700(3) -0.4292(3) -0.3456(2) 0.0525(8) Uani 1 1 d . . . . .
H23 H 0.0835 -0.4734 -0.4109 0.063 Uiso 1 1 calc R U . . .
C6 C 0.2261(3) 0.5442(3) -0.0134(2) 0.0488(7) Uani 1 1 d . . . . .
H6 H 0.2373 0.6262 -0.0085 0.059 Uiso 1 1 calc R U . . .
C31 C 0.7116(4) 0.0463(3) 0.4712(2) 0.0578(9) Uani 1 1 d . . . . .
C30 C 0.7633(3) -0.0284(3) 0.3941(3) 0.0616(9) Uani 1 1 d . . . . .
H30 H 0.8381 -0.0582 0.4091 0.074 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Er1 O4 2.2588(17) . ?
Er1 O6 2.2994(17) . ?
Er1 O5 2.3024(17) . ?
Er1 O3 2.3030(16) . ?
Er1 O1 2.3354(17) . ?
Er1 O2 2.4671(17) . ?
Er1 N2 2.5281(19) . ?
Er1 N1 2.6051(18) . ?
Er1 C13 2.754(2) . ?
Cl1 C17 1.743(3) . ?
Cl2 C24 1.740(3) . ?
Cl3 C31 1.743(3) . ?
C25 C24 1.376(4) . ?
C25 C26 1.394(3) . ?
C25 H25 0.9300 . ?
O1 C13 1.276(3) . ?
O2 C13 1.257(3) . ?
O5 C27 1.252(3) . ?
O6 C27 1.258(3) 2_655 ?
O3 C20 1.252(3) . ?
N2 C10 1.332(3) . ?
N2 C11 1.356(3) . ?
O4 C20 1.251(3) 2_655 ?
C12 N1 1.360(3) . ?
C12 C4 1.408(3) . ?
C12 C11 1.442(3) . ?
N1 C1 1.329(3) . ?
C20 O4 1.251(3) 2_655 ?
C20 C21 1.500(3) . ?
C13 C14 1.496(3) . ?
C27 O6 1.258(3) 2_655 ?
C27 C28 1.504(3) . ?
C11 C7 1.418(3) . ?
C21 C26 1.379(3) . ?
C21 C22 1.388(3) . ?
C14 C15 1.379(4) . ?
C14 C19 1.392(4) . ?
C28 C33 1.382(4) . ?
C28 C29 1.387(4) . ?
C1 C2 1.395(3) . ?
C1 H1 0.9300 . ?
C7 C8 1.401(4) . ?
C7 C6 1.431(4) . ?
C5 C6 1.329(4) . ?
C5 C4 1.435(4) . ?
C5 H5 0.9300 . ?
C4 C3 1.397(4) . ?
C29 C30 1.391(4) . ?
C29 H29 0.9300 . ?
C17 C18 1.366(4) . ?
C17 C16 1.382(4) . ?
C10 C9 1.395(4) . ?
C10 H10 0.9300 . ?
C24 C23 1.374(4) . ?
C26 H26 0.9300 . ?
C33 C32 1.389(4) . ?
C33 H33 0.9300 . ?
C18 C19 1.394(4) . ?
C18 H18 0.9300 . ?
C3 C2 1.366(4) . ?
C3 H3 0.9300 . ?
C8 C9 1.358(4) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C15 C16 1.379(4) . ?
C15 H15 0.9300 . ?
C2 H2 0.9300 . ?
C19 H19 0.9300 . ?
C16 H16 0.9300 . ?
C22 C23 1.381(4) . ?
C22 H22 0.9300 . ?
C32 C31 1.356(5) . ?
C32 H32 0.9300 . ?
C23 H23 0.9300 . ?
C6 H6 0.9300 . ?
C31 C30 1.368(5) . ?
C30 H30 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 Er1 O6 79.11(6) . . ?
O4 Er1 O5 76.17(7) . . ?
O6 Er1 O5 124.85(6) . . ?
O4 Er1 O3 123.92(7) . . ?
O6 Er1 O3 78.22(7) . . ?
O5 Er1 O3 76.29(6) . . ?
O4 Er1 O1 132.29(6) . . ?
O6 Er1 O1 146.34(6) . . ?
O5 Er1 O1 80.87(6) . . ?
O3 Er1 O1 89.26(6) . . ?
O4 Er1 O2 79.25(6) . . ?
O6 Er1 O2 145.16(6) . . ?
O5 Er1 O2 75.14(6) . . ?
O3 Er1 O2 136.62(6) . . ?
O1 Er1 O2 54.49(6) . . ?
O4 Er1 N2 85.12(7) . . ?
O6 Er1 N2 80.60(6) . . ?
O5 Er1 N2 143.45(6) . . ?
O3 Er1 N2 139.14(6) . . ?
O1 Er1 N2 89.44(6) . . ?
O2 Er1 N2 70.64(6) . . ?
O4 Er1 N1 140.09(7) . . ?
O6 Er1 N1 71.68(6) . . ?
O5 Er1 N1 143.36(6) . . ?
O3 Er1 N1 76.21(6) . . ?
O1 Er1 N1 75.04(6) . . ?
O2 Er1 N1 110.59(6) . . ?
N2 Er1 N1 64.05(6) . . ?
O4 Er1 C13 105.23(7) . . ?
O6 Er1 C13 160.52(7) . . ?
O5 Er1 C13 74.36(7) . . ?
O3 Er1 C13 112.80(7) . . ?
O1 Er1 C13 27.49(7) . . ?
O2 Er1 C13 27.15(7) . . ?
N2 Er1 C13 80.87(7) . . ?
N1 Er1 C13 94.72(7) . . ?
C24 C25 C26 118.7(3) . . ?
C24 C25 H25 120.7 . . ?
C26 C25 H25 120.7 . . ?
C13 O1 Er1 94.85(15) . . ?
C13 O2 Er1 89.25(14) . . ?
C27 O5 Er1 137.49(17) . . ?
C27 O6 Er1 137.60(16) 2_655 . ?
C20 O3 Er1 130.65(16) . . ?
C10 N2 C11 117.8(2) . . ?
C10 N2 Er1 121.03(16) . . ?
C11 N2 Er1 121.13(15) . . ?
C20 O4 Er1 159.44(18) 2_655 . ?
N1 C12 C4 122.9(2) . . ?
N1 C12 C11 118.1(2) . . ?
C4 C12 C11 119.0(2) . . ?
C1 N1 C12 117.3(2) . . ?
C1 N1 Er1 124.44(16) . . ?
C12 N1 Er1 118.24(15) . . ?
O4 C20 O3 125.0(2) 2_655 . ?
O4 C20 C21 117.2(2) 2_655 . ?
O3 C20 C21 117.8(2) . . ?
O2 C13 O1 120.7(2) . . ?
O2 C13 C14 120.0(2) . . ?
O1 C13 C14 119.2(2) . . ?
O2 C13 Er1 63.59(13) . . ?
O1 C13 Er1 57.66(12) . . ?
C14 C13 Er1 170.27(17) . . ?
O5 C27 O6 125.3(2) . 2_655 ?
O5 C27 C28 118.0(2) . . ?
O6 C27 C28 116.8(2) 2_655 . ?
N2 C11 C7 122.5(2) . . ?
N2 C11 C12 118.2(2) . . ?
C7 C11 C12 119.3(2) . . ?
C26 C21 C22 119.5(2) . . ?
C26 C21 C20 120.3(2) . . ?
C22 C21 C20 120.1(2) . . ?
C15 C14 C19 119.2(2) . . ?
C15 C14 C13 120.9(2) . . ?
C19 C14 C13 120.0(2) . . ?
C33 C28 C29 119.1(2) . . ?
C33 C28 C27 120.3(2) . . ?
C29 C28 C27 120.6(2) . . ?
N1 C1 C2 123.8(2) . . ?
N1 C1 H1 118.1 . . ?
C2 C1 H1 118.1 . . ?
C8 C7 C11 117.3(2) . . ?
C8 C7 C6 123.4(2) . . ?
C11 C7 C6 119.3(2) . . ?
C6 C5 C4 121.5(3) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C3 C4 C12 117.5(2) . . ?
C3 C4 C5 122.9(2) . . ?
C12 C4 C5 119.5(2) . . ?
C28 C29 C30 120.4(3) . . ?
C28 C29 H29 119.8 . . ?
C30 C29 H29 119.8 . . ?
C18 C17 C16 121.6(3) . . ?
C18 C17 Cl1 119.6(2) . . ?
C16 C17 Cl1 118.8(2) . . ?
N2 C10 C9 123.0(3) . . ?
N2 C10 H10 118.5 . . ?
C9 C10 H10 118.5 . . ?
C23 C24 C25 121.4(3) . . ?
C23 C24 Cl2 119.4(2) . . ?
C25 C24 Cl2 119.1(2) . . ?
C21 C26 C25 120.6(2) . . ?
C21 C26 H26 119.7 . . ?
C25 C26 H26 119.7 . . ?
C28 C33 C32 120.3(3) . . ?
C28 C33 H33 119.8 . . ?
C32 C33 H33 119.8 . . ?
C17 C18 C19 119.4(3) . . ?
C17 C18 H18 120.3 . . ?
C19 C18 H18 120.3 . . ?
C2 C3 C4 119.8(2) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C9 C8 C7 119.7(3) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C8 C9 C10 119.6(3) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C16 C15 C14 121.3(3) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C3 C2 C1 118.8(2) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C14 C19 C18 119.9(3) . . ?
C14 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C15 C16 C17 118.7(3) . . ?
C15 C16 H16 120.7 . . ?
C17 C16 H16 120.7 . . ?
C23 C22 C21 120.1(3) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C31 C32 C33 119.4(3) . . ?
C31 C32 H32 120.3 . . ?
C33 C32 H32 120.3 . . ?
C24 C23 C22 119.6(3) . . ?
C24 C23 H23 120.2 . . ?
C22 C23 H23 120.2 . . ?
C5 C6 C7 121.2(3) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C32 C31 C30 121.9(3) . . ?
C32 C31 Cl3 120.0(3) . . ?
C30 C31 Cl3 118.2(3) . . ?
C31 C30 C29 118.9(3) . . ?
C31 C30 H30 120.5 . . ?
C29 C30 H30 120.5 . . ?

_refine_diff_density_max         0.555
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.081

_shelxl_version_number           2013-4

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_h-m   'P -1'
_symmetry_int_tables_number      2
_chemical_absolute_configuration ?
_database_code_depnum_ccdc_archive 'CCDC 1018744'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_Compound_8


_audit_creation_method           SHELXL-2013
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C66 H40 Cl6 N4 O12 Tm2'
_chemical_melting_point          ?

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colorless

_diffrn_ambient_temperature      293(2)
_chemical_formula_weight         1631.58

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'
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'
Cl Cl 0.1484 0.1585 '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'

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

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

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

_cell_length_a                   10.1079(3)
_cell_length_b                   11.8190(3)
_cell_length_c                   14.2667(4)
_cell_angle_alpha                111.320(2)
_cell_angle_beta                 96.529(3)
_cell_angle_gamma                101.207(2)
_cell_volume                     1525.43(8)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    22033
_cell_measurement_theta_min      4.700
_cell_measurement_theta_max      51.877
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.776
_exptl_crystal_F_000             800
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    3.220
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6555
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   'SADABS, Bruker-AXS (2008)'

_exptl_special_details           
;
 ?
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22033
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.564
_diffrn_reflns_theta_max         28.850
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7934
_reflns_number_gt                6909
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX, Bruker-AXS'
_computing_cell_refinement       'SAINT, Bruker-AXS'
_computing_data_reduction        'SAINT, Bruker-AXS'
_computing_structure_solution    'SIR92 (Gualardi, 1994)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Crystal Maker (Palmer, 2009)'
_computing_publication_material  'WINGX (Farrugia, 2012)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0273P)²+0.1724P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7934
_refine_ls_number_parameters     406
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0267
_refine_ls_wR_factor_ref         0.0586
_refine_ls_wR_factor_gt          0.0554
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Tm1 Tm 0.12223(2) 0.37146(2) 0.93532(2) 0.02535(4) Uani 1 1 d . . . . .
Cl1 Cl 0.36419(12) 0.18813(11) 0.34230(7) 0.0707(3) Uani 1 1 d . . . . .
Cl2 Cl 0.68862(12) 1.07758(10) 1.40957(9) 0.0849(4) Uani 1 1 d . . . . .
Cl3 Cl -0.28806(16) 0.41818(13) 0.40243(8) 0.1035(5) Uani 1 1 d . . . . .
O2 O 0.0732(2) 0.2376(2) 0.75085(16) 0.0414(5) Uani 1 1 d . . . . .
C23 C 0.5777(3) 0.8907(3) 1.2237(3) 0.0433(8) Uani 1 1 d . . . . .
H23 H 0.6625 0.9117 1.2066 0.052 Uiso 1 1 calc R U . . .
O5 O 0.0712(2) 0.4981(2) 0.85430(15) 0.0426(5) Uani 1 1 d . . . . .
O3 O 0.2581(2) 0.56671(18) 1.04092(16) 0.0413(5) Uani 1 1 d . . . . .
O1 O 0.2833(2) 0.3503(2) 0.83020(15) 0.0385(5) Uani 1 1 d . . . . .
O6 O 0.0765(2) 0.3863(2) 1.09192(15) 0.0395(5) Uani 1 1 d . . . . .
N2 N 0.0919(2) 0.1455(2) 0.91196(17) 0.0315(5) Uani 1 1 d . . . . .
O4 O -0.1093(2) 0.3224(2) 0.90013(17) 0.0472(6) Uani 1 1 d . . . . .
C20 C 0.2285(3) 0.6621(3) 1.0998(2) 0.0324(6) Uani 1 1 d . . . . .
N1 N 0.3233(2) 0.3239(2) 1.03224(16) 0.0286(5) Uani 1 1 d . . . . .
C14 C 0.2393(3) 0.2522(3) 0.6468(2) 0.0379(7) Uani 1 1 d . . . . .
C13 C 0.1956(3) 0.2802(3) 0.7481(2) 0.0349(7) Uani 1 1 d . . . . .
C12 C 0.3077(3) 0.2058(3) 1.0295(2) 0.0289(6) Uani 1 1 d . . . . .
C21 C 0.3437(3) 0.7659(2) 1.1772(2) 0.0297(6) Uani 1 1 d . . . . .
C11 C 0.1866(3) 0.1106(2) 0.9634(2) 0.0298(6) Uani 1 1 d . . . . .
C27 C -0.0265(3) 0.5443(3) 0.8393(2) 0.0308(6) Uani 1 1 d . . . . .
C28 C -0.0899(3) 0.5147(3) 0.7296(2) 0.0344(6) Uani 1 1 d . . . . .
C1 C 0.4387(3) 0.4091(3) 1.0890(2) 0.0363(7) Uani 1 1 d . . . . .
H1 H 0.4508 0.4903 1.0916 0.044 Uiso 1 1 calc R U . . .
C4 C 0.4062(3) 0.1718(3) 1.0845(2) 0.0362(7) Uani 1 1 d . . . . .
C3 C 0.5262(3) 0.2651(3) 1.1436(2) 0.0439(8) Uani 1 1 d . . . . .
H3 H 0.5936 0.2465 1.1814 0.053 Uiso 1 1 calc R U . . .
C7 C 0.1722(3) -0.0149(3) 0.9531(2) 0.0384(7) Uani 1 1 d . . . . .
C5 C 0.3842(4) 0.0446(3) 1.0758(3) 0.0473(8) Uani 1 1 d . . . . .
H5 H 0.4479 0.0234 1.1145 0.057 Uiso 1 1 calc R U . . .
C17 C 0.3149(4) 0.2098(3) 0.4600(2) 0.0508(9) Uani 1 1 d . . . . .
C16 C 0.1812(4) 0.1639(4) 0.4617(3) 0.0618(11) Uani 1 1 d . . . . .
H16 H 0.1167 0.1189 0.4007 0.074 Uiso 1 1 calc R U . . .
C26 C 0.3228(3) 0.8350(3) 1.2741(2) 0.0427(7) Uani 1 1 d . . . . .
H26 H 0.2368 0.8178 1.2906 0.051 Uiso 1 1 calc R U . . .
C22 C 0.4715(3) 0.7926(3) 1.1527(2) 0.0347(6) Uani 1 1 d . . . . .
H22 H 0.4865 0.7449 1.0887 0.042 Uiso 1 1 calc R U . . .
C10 C -0.0166(3) 0.0560(3) 0.8481(2) 0.0401(7) Uani 1 1 d . . . . .
H10 H -0.0821 0.0788 0.8122 0.048 Uiso 1 1 calc R U . . .
C18 C 0.4133(4) 0.2747(3) 0.5487(3) 0.0503(8) Uani 1 1 d . . . . .
H18 H 0.5046 0.3037 0.5459 0.060 Uiso 1 1 calc R U . . .
C19 C 0.3742(3) 0.2958(3) 0.6420(2) 0.0442(8) Uani 1 1 d . . . . .
H19 H 0.4398 0.3401 0.7025 0.053 Uiso 1 1 calc R U . . .
C33 C -0.2019(4) 0.5588(3) 0.7076(3) 0.0484(8) Uani 1 1 d . . . . .
H33 H -0.2364 0.6092 0.7609 0.058 Uiso 1 1 calc R U . . .
C29 C -0.0409(4) 0.4396(3) 0.6498(2) 0.0519(9) Uani 1 1 d . . . . .
H29 H 0.0340 0.4093 0.6638 0.062 Uiso 1 1 calc R U . . .
C8 C 0.0562(4) -0.1051(3) 0.8851(3) 0.0497(8) Uani 1 1 d . . . . .
H8 H 0.0428 -0.1888 0.8761 0.060 Uiso 1 1 calc R U . . .
C2 C 0.5432(3) 0.3831(3) 1.1452(2) 0.0445(8) Uani 1 1 d . . . . .
H2 H 0.6229 0.4454 1.1830 0.053 Uiso 1 1 calc R U . . .
C32 C -0.2629(4) 0.5277(4) 0.6063(3) 0.0629(11) Uani 1 1 d . . . . .
H32 H -0.3384 0.5570 0.5915 0.076 Uiso 1 1 calc R U . . .
C9 C -0.0368(4) -0.0701(3) 0.8323(3) 0.0503(9) Uani 1 1 d . . . . .
H9 H -0.1134 -0.1297 0.7860 0.060 Uiso 1 1 calc R U . . .
C24 C 0.5549(3) 0.9561(3) 1.3197(3) 0.0475(8) Uani 1 1 d . . . . .
C6 C 0.2735(4) -0.0442(3) 1.0128(3) 0.0482(8) Uani 1 1 d . . . . .
H6 H 0.2622 -0.1264 1.0078 0.058 Uiso 1 1 calc R U . . .
C15 C 0.1421(4) 0.1851(3) 0.5557(2) 0.0517(9) Uani 1 1 d . . . . .
H15 H 0.0509 0.1544 0.5578 0.062 Uiso 1 1 calc R U . . .
C30 C -0.1021(5) 0.4086(4) 0.5483(3) 0.0661(11) Uani 1 1 d . . . . .
H30 H -0.0689 0.3575 0.4945 0.079 Uiso 1 1 calc R U . . .
C25 C 0.4297(4) 0.9289(3) 1.3456(3) 0.0546(9) Uani 1 1 d . . . . .
H25 H 0.4169 0.9736 1.4111 0.065 Uiso 1 1 calc R U . . .
C31 C -0.2116(4) 0.4541(4) 0.5286(3) 0.0596(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
Tm1 O4 2.249(2) . ?
Tm1 O6 2.2841(19) . ?
Tm1 O3 2.291(2) . ?
Tm1 O5 2.294(2) . ?
Tm1 O1 2.324(2) . ?
Tm1 O2 2.459(2) . ?
Tm1 N2 2.519(2) . ?
Tm1 N1 2.594(2) . ?
Tm1 C13 2.742(3) . ?
Cl1 C17 1.750(3) . ?
Cl2 C24 1.745(3) . ?
Cl3 C31 1.737(3) . ?
O2 C13 1.253(4) . ?
C23 C24 1.378(5) . ?
C23 C22 1.392(4) . ?
C23 H23 0.9300 . ?
O5 C27 1.251(3) . ?
O3 C20 1.251(3) . ?
O1 C13 1.272(4) . ?
O6 C27 1.256(3) 2_567 ?
N2 C10 1.332(4) . ?
N2 C11 1.356(3) . ?
O4 C20 1.254(3) 2_567 ?
C20 O4 1.254(3) 2_567 ?
C20 C21 1.498(4) . ?
N1 C1 1.329(4) . ?
N1 C12 1.359(3) . ?
C14 C19 1.380(4) . ?
C14 C15 1.393(4) . ?
C14 C13 1.499(4) . ?
C12 C4 1.406(4) . ?
C12 C11 1.444(4) . ?
C21 C22 1.384(4) . ?
C21 C26 1.392(4) . ?
C11 C7 1.413(4) . ?
C27 O6 1.256(3) 2_567 ?
C27 C28 1.506(4) . ?
C28 C29 1.377(4) . ?
C28 C33 1.386(4) . ?
C1 C2 1.401(4) . ?
C1 H1 0.9300 . ?
C4 C3 1.403(5) . ?
C4 C5 1.433(4) . ?
C3 C2 1.363(5) . ?
C3 H3 0.9300 . ?
C7 C8 1.399(5) . ?
C7 C6 1.431(5) . ?
C5 C6 1.338(5) . ?
C5 H5 0.9300 . ?
C17 C16 1.361(5) . ?
C17 C18 1.375(5) . ?
C16 C15 1.390(5) . ?
C16 H16 0.9300 . ?
C26 C25 1.378(5) . ?
C26 H26 0.9300 . ?
C22 H22 0.9300 . ?
C10 C9 1.394(4) . ?
C10 H10 0.9300 . ?
C18 C19 1.381(4) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C33 C32 1.389(5) . ?
C33 H33 0.9300 . ?
C29 C30 1.392(5) . ?
C29 H29 0.9300 . ?
C8 C9 1.356(5) . ?
C8 H8 0.9300 . ?
C2 H2 0.9300 . ?
C32 C31 1.364(5) . ?
C32 H32 0.9300 . ?
C9 H9 0.9300 . ?
C24 C25 1.370(5) . ?
C6 H6 0.9300 . ?
C15 H15 0.9300 . ?
C30 C31 1.366(5) . ?
C30 H30 0.9300 . ?
C25 H25 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 Tm1 O6 79.26(8) . . ?
O4 Tm1 O3 124.05(8) . . ?
O6 Tm1 O3 78.35(8) . . ?
O4 Tm1 O5 76.16(8) . . ?
O6 Tm1 O5 124.92(7) . . ?
O3 Tm1 O5 76.20(8) . . ?
O4 Tm1 O1 132.18(8) . . ?
O6 Tm1 O1 146.34(7) . . ?
O3 Tm1 O1 89.07(8) . . ?
O5 Tm1 O1 80.74(7) . . ?
O4 Tm1 O2 79.04(8) . . ?
O6 Tm1 O2 145.23(8) . . ?
O3 Tm1 O2 136.42(8) . . ?
O5 Tm1 O2 74.96(7) . . ?
O1 Tm1 O2 54.58(7) . . ?
O4 Tm1 N2 84.73(8) . . ?
O6 Tm1 N2 80.51(7) . . ?
O3 Tm1 N2 139.48(7) . . ?
O5 Tm1 N2 143.25(8) . . ?
O1 Tm1 N2 89.80(7) . . ?
O2 Tm1 N2 70.73(7) . . ?
O4 Tm1 N1 140.14(8) . . ?
O6 Tm1 N1 71.76(7) . . ?
O3 Tm1 N1 76.39(7) . . ?
O5 Tm1 N1 143.36(8) . . ?
O1 Tm1 N1 74.99(7) . . ?
O2 Tm1 N1 110.59(7) . . ?
N2 Tm1 N1 64.27(7) . . ?
O4 Tm1 C13 105.09(9) . . ?
O6 Tm1 C13 160.57(8) . . ?
O3 Tm1 C13 112.63(9) . . ?
O5 Tm1 C13 74.24(8) . . ?
O1 Tm1 C13 27.52(8) . . ?
O2 Tm1 C13 27.20(8) . . ?
N2 Tm1 C13 81.05(8) . . ?
N1 Tm1 C13 94.64(8) . . ?
C13 O2 Tm1 89.07(17) . . ?
C24 C23 C22 118.8(3) . . ?
C24 C23 H23 120.6 . . ?
C22 C23 H23 120.6 . . ?
C27 O5 Tm1 137.59(19) . . ?
C20 O3 Tm1 131.19(19) . . ?
C13 O1 Tm1 94.83(17) . . ?
C27 O6 Tm1 137.38(18) 2_567 . ?
C10 N2 C11 117.6(2) . . ?
C10 N2 Tm1 121.36(19) . . ?
C11 N2 Tm1 121.03(17) . . ?
C20 O4 Tm1 158.7(2) 2_567 . ?
O3 C20 O4 125.0(3) . 2_567 ?
O3 C20 C21 117.9(2) . . ?
O4 C20 C21 117.1(3) 2_567 . ?
C1 N1 C12 117.3(2) . . ?
C1 N1 Tm1 124.33(18) . . ?
C12 N1 Tm1 118.27(17) . . ?
C19 C14 C15 119.1(3) . . ?
C19 C14 C13 120.9(3) . . ?
C15 C14 C13 119.9(3) . . ?
O2 C13 O1 120.9(3) . . ?
O2 C13 C14 120.0(3) . . ?
O1 C13 C14 119.1(3) . . ?
O2 C13 Tm1 63.73(15) . . ?
O1 C13 Tm1 57.65(14) . . ?
C14 C13 Tm1 170.5(2) . . ?
N1 C12 C4 123.0(3) . . ?
N1 C12 C11 117.9(2) . . ?
C4 C12 C11 119.0(3) . . ?
C22 C21 C26 119.8(3) . . ?
C22 C21 C20 120.1(2) . . ?
C26 C21 C20 120.1(3) . . ?
N2 C11 C7 122.6(3) . . ?
N2 C11 C12 118.2(2) . . ?
C7 C11 C12 119.2(3) . . ?
O5 C27 O6 125.6(3) . 2_567 ?
O5 C27 C28 117.5(3) . . ?
O6 C27 C28 116.9(2) 2_567 . ?
C29 C28 C33 119.0(3) . . ?
C29 C28 C27 120.6(3) . . ?
C33 C28 C27 120.4(3) . . ?
N1 C1 C2 123.5(3) . . ?
N1 C1 H1 118.2 . . ?
C2 C1 H1 118.2 . . ?
C3 C4 C12 117.6(3) . . ?
C3 C4 C5 122.5(3) . . ?
C12 C4 C5 119.9(3) . . ?
C2 C3 C4 119.5(3) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C8 C7 C11 117.4(3) . . ?
C8 C7 C6 123.1(3) . . ?
C11 C7 C6 119.5(3) . . ?
C6 C5 C4 121.1(3) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C16 C17 C18 121.9(3) . . ?
C16 C17 Cl1 119.6(3) . . ?
C18 C17 Cl1 118.4(3) . . ?
C17 C16 C15 119.2(3) . . ?
C17 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
C25 C26 C21 119.9(3) . . ?
C25 C26 H26 120.0 . . ?
C21 C26 H26 120.0 . . ?
C21 C22 C23 120.1(3) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
N2 C10 C9 123.2(3) . . ?
N2 C10 H10 118.4 . . ?
C9 C10 H10 118.4 . . ?
C17 C18 C19 118.8(3) . . ?
C17 C18 H18 120.6 . . ?
C19 C18 H18 120.6 . . ?
C14 C19 C18 121.0(3) . . ?
C14 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
C28 C33 C32 120.2(3) . . ?
C28 C33 H33 119.9 . . ?
C32 C33 H33 119.9 . . ?
C28 C29 C30 120.8(3) . . ?
C28 C29 H29 119.6 . . ?
C30 C29 H29 119.6 . . ?
C9 C8 C7 119.8(3) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C3 C2 C1 119.0(3) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C31 C32 C33 119.7(3) . . ?
C31 C32 H32 120.2 . . ?
C33 C32 H32 120.2 . . ?
C8 C9 C10 119.4(3) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
C25 C24 C23 121.6(3) . . ?
C25 C24 Cl2 119.5(3) . . ?
C23 C24 Cl2 118.9(3) . . ?
C5 C6 C7 121.1(3) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C16 C15 C14 120.0(3) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C31 C30 C29 119.1(3) . . ?
C31 C30 H30 120.5 . . ?
C29 C30 H30 120.5 . . ?
C24 C25 C26 119.7(3) . . ?
C24 C25 H25 120.2 . . ?
C26 C25 H25 120.2 . . ?
C32 C31 C30 121.3(3) . . ?
C32 C31 Cl3 118.9(3) . . ?
C30 C31 Cl3 119.8(3) . . ?

_refine_diff_density_max         0.726
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.094

_shelxl_version_number           2013-4

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_h-m   'P -1'
_symmetry_int_tables_number      2
_chemical_absolute_configuration ?
_database_code_depnum_ccdc_archive 'CCDC 1018745'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_Compound_9

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C66 H40 Cl6 N4 O12 Yb2'
_chemical_melting_point          ?

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colorless

_diffrn_ambient_temperature      293(2)
_chemical_formula_weight         1639.80

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Yb Yb -0.3850 5.5486 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   10.0937(8)
_cell_length_b                   11.8057(9)
_cell_length_c                   14.2502(11)
_cell_angle_alpha                111.386(5)
_cell_angle_beta                 96.465(4)
_cell_angle_gamma                101.209(5)
_cell_volume                     1519.4(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    21595
_cell_measurement_theta_min      4.708
_cell_measurement_theta_max      48.526
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.792
_exptl_crystal_F_000             802
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    3.391
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6707
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS, Bruker-AXS (2008)'

_exptl_special_details           
;
 ?
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21595
_diffrn_reflns_av_unetI/netI     0.0453
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.567
_diffrn_reflns_theta_max         28.464
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7640
_reflns_number_gt                6571
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX, Bruker-AXS'
_computing_cell_refinement       'SAINT, Bruker-AXS'
_computing_data_reduction        'SAINT, Bruker-AXS'
_computing_structure_solution    'SIR92 (Gualardi, 1994)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Crystal Maker (Palmer, 2009)'
_computing_publication_material  'WINGX (Farrugia, 2012)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0263P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7640
_refine_ls_number_parameters     406
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0284
_refine_ls_wR_factor_ref         0.0586
_refine_ls_wR_factor_gt          0.0551
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_restrained_S_all      0.995
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Yb1 Yb 0.37796(2) 0.12890(2) 0.06465(2) 0.02380(5) Uani 1 1 d . . . . .
Cl1 Cl 0.13484(12) 0.31166(12) 0.65765(8) 0.0657(3) Uani 1 1 d . . . . .
Cl2 Cl -0.18896(12) -0.57761(11) -0.40978(10) 0.0797(4) Uani 1 1 d . . . . .
Cl3 Cl 0.78769(16) 0.08172(14) 0.59783(9) 0.0975(5) Uani 1 1 d . . . . .
C13 C 0.3051(4) 0.2204(3) 0.2519(2) 0.0323(7) Uani 1 1 d . . . . .
O2 O 0.4276(2) 0.2629(2) 0.24897(16) 0.0384(5) Uani 1 1 d . . . . .
O3 O 0.2429(2) -0.06596(19) -0.04065(17) 0.0378(5) Uani 1 1 d . . . . .
O1 O 0.2170(2) 0.1499(2) 0.16921(16) 0.0354(5) Uani 1 1 d . . . . .
N2 N 0.4088(3) 0.3543(2) 0.08791(19) 0.0298(6) Uani 1 1 d . . . . .
O5 O 0.4288(2) 0.0030(2) 0.14571(17) 0.0404(6) Uani 1 1 d . . . . .
O4 O 0.6091(2) 0.1782(2) 0.09941(18) 0.0440(6) Uani 1 1 d . . . . .
O6 O 0.4232(2) 0.1129(2) -0.09164(17) 0.0384(5) Uani 1 1 d . . . . .
C20 C 0.2719(3) -0.1618(3) -0.0996(2) 0.0304(7) Uani 1 1 d . . . . .
C16 C 0.0858(4) 0.2255(4) 0.4509(3) 0.0473(9) Uani 1 1 d . . . . .
H16 H -0.0056 0.1966 0.4536 0.057 Uiso 1 1 calc R U . . .
N1 N 0.1775(2) 0.1756(2) -0.03222(18) 0.0263(5) Uani 1 1 d . . . . .
C14 C 0.2604(3) 0.2477(3) 0.3531(2) 0.0340(7) Uani 1 1 d . . . . .
C4 C 0.0939(3) 0.3277(3) -0.0844(2) 0.0334(7) Uani 1 1 d . . . . .
C21 C 0.1569(3) -0.2659(3) -0.1768(2) 0.0272(6) Uani 1 1 d . . . . .
C11 C 0.3139(3) 0.3897(3) 0.0368(2) 0.0282(7) Uani 1 1 d . . . . .
C1 C 0.0613(3) 0.0907(3) -0.0886(2) 0.0335(7) Uani 1 1 d . . . . .
H1 H 0.0489 0.0094 -0.0911 0.040 Uiso 1 1 calc R U . . .
C27 C 0.5264(3) -0.0434(3) 0.1613(2) 0.0284(7) Uani 1 1 d . . . . .
C12 C 0.1929(3) 0.2944(3) -0.0289(2) 0.0268(6) Uani 1 1 d . . . . .
C23 C -0.0773(3) -0.3906(3) -0.2237(3) 0.0389(8) Uani 1 1 d . . . . .
H23 H -0.1621 -0.4114 -0.2064 0.047 Uiso 1 1 calc R U . . .
C28 C 0.5898(3) -0.0147(3) 0.2706(2) 0.0320(7) Uani 1 1 d . . . . .
C6 C 0.2264(4) 0.5443(3) -0.0128(3) 0.0456(9) Uani 1 1 d . . . . .
H6 H 0.2374 0.6265 -0.0078 0.055 Uiso 1 1 calc R U . . .
C3 C -0.0255(4) 0.2347(4) -0.1428(3) 0.0431(9) Uani 1 1 d . . . . .
H3 H -0.0929 0.2533 -0.1807 0.052 Uiso 1 1 calc R U . . .
C18 C 0.3190(4) 0.3367(4) 0.5383(3) 0.0571(11) Uani 1 1 d . . . . .
H18 H 0.3837 0.3817 0.5993 0.069 Uiso 1 1 calc R U . . .
C5 C 0.1165(4) 0.4553(3) -0.0755(3) 0.0441(9) Uani 1 1 d . . . . .
H5 H 0.0528 0.4763 -0.1145 0.053 Uiso 1 1 calc R U . . .
C8 C 0.4438(4) 0.6055(3) 0.1158(3) 0.0460(9) Uani 1 1 d . . . . .
H8 H 0.4565 0.6896 0.1257 0.055 Uiso 1 1 calc R U . . .
C29 C 0.5405(4) 0.0608(4) 0.3505(3) 0.0479(9) Uani 1 1 d . . . . .
H29 H 0.4654 0.0911 0.3366 0.057 Uiso 1 1 calc R U . . .
C32 C 0.7631(4) -0.0279(4) 0.3932(3) 0.0578(11) Uani 1 1 d . . . . .
H32 H 0.8386 -0.0572 0.4080 0.069 Uiso 1 1 calc R U . . .
C17 C 0.1844(4) 0.2904(4) 0.5401(3) 0.0487(9) Uani 1 1 d . . . . .
C15 C 0.1257(4) 0.2041(3) 0.3571(3) 0.0405(8) Uani 1 1 d . . . . .
H15 H 0.0605 0.1598 0.2963 0.049 Uiso 1 1 calc R U . . .
C10 C 0.5176(3) 0.4438(3) 0.1524(3) 0.0375(8) Uani 1 1 d . . . . .
H10 H 0.5828 0.4210 0.1886 0.045 Uiso 1 1 calc R U . . .
C33 C 0.7022(4) -0.0587(3) 0.2922(3) 0.0458(9) Uani 1 1 d . . . . .
H33 H 0.7367 -0.1090 0.2388 0.055 Uiso 1 1 calc R U . . .
C24 C -0.0551(4) -0.4569(3) -0.3196(3) 0.0432(9) Uani 1 1 d . . . . .
C26 C 0.1771(3) -0.3349(3) -0.2738(3) 0.0394(8) Uani 1 1 d . . . . .
H26 H 0.2631 -0.3176 -0.2904 0.047 Uiso 1 1 calc R U . . .
C22 C 0.0282(3) -0.2927(3) -0.1533(2) 0.0321(7) Uani 1 1 d . . . . .
H22 H 0.0125 -0.2444 -0.0896 0.039 Uiso 1 1 calc R U . . .
C9 C 0.5376(4) 0.5700(3) 0.1678(3) 0.0466(9) Uani 1 1 d . . . . .
H9 H 0.6148 0.6296 0.2135 0.056 Uiso 1 1 calc R U . . .
C2 C -0.0435(4) 0.1169(3) -0.1445(3) 0.0427(8) Uani 1 1 d . . . . .
H2 H -0.1237 0.0549 -0.1820 0.051 Uiso 1 1 calc R U . . .
C19 C 0.3573(4) 0.3152(4) 0.4440(3) 0.0482(9) Uani 1 1 d . . . . .
H19 H 0.4484 0.3462 0.4417 0.058 Uiso 1 1 calc R U . . .
C25 C 0.0704(4) -0.4290(4) -0.3459(3) 0.0496(10) Uani 1 1 d . . . . .
H25 H 0.0833 -0.4732 -0.4117 0.059 Uiso 1 1 calc R U . . .
C7 C 0.3280(4) 0.5151(3) 0.0472(3) 0.0367(8) Uani 1 1 d . . . . .
C31 C 0.7112(4) 0.0462(4) 0.4712(3) 0.0556(11) Uani 1 1 d . . . . .
C30 C 0.6023(5) 0.0918(4) 0.4518(3) 0.0613(12) Uani 1 1 d . . . . .
H30 H 0.5695 0.1433 0.5058 0.074 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Yb1 O4 2.242(2) . ?
Yb1 O6 2.272(2) . ?
Yb1 O3 2.281(2) . ?
Yb1 O5 2.285(2) . ?
Yb1 O1 2.314(2) . ?
Yb1 O2 2.453(2) . ?
Yb1 N2 2.509(2) . ?
Yb1 N1 2.581(2) . ?
Cl1 C17 1.747(4) . ?
Cl2 C24 1.742(3) . ?
Cl3 C31 1.743(4) . ?
C13 O2 1.252(4) . ?
C13 O1 1.278(4) . ?
C13 C14 1.500(4) . ?
O3 C20 1.250(4) . ?
N2 C10 1.335(4) . ?
N2 C11 1.357(4) . ?
O5 C27 1.252(4) . ?
O4 C20 1.254(4) 2_655 ?
O6 C27 1.265(4) 2_655 ?
C20 O4 1.254(4) 2_655 ?
C20 C21 1.497(4) . ?
C16 C17 1.378(5) . ?
C16 C15 1.389(5) . ?
C16 H16 0.9300 . ?
N1 C1 1.330(4) . ?
N1 C12 1.364(4) . ?
C14 C15 1.372(5) . ?
C14 C19 1.389(5) . ?
C4 C3 1.394(5) . ?
C4 C12 1.408(4) . ?
C4 C5 1.434(5) . ?
C21 C22 1.384(4) . ?
C21 C26 1.387(4) . ?
C11 C7 1.410(4) . ?
C11 C12 1.440(4) . ?
C1 C2 1.403(4) . ?
C1 H1 0.9300 . ?
C27 O6 1.265(4) 2_655 ?
C27 C28 1.503(4) . ?
C23 C24 1.374(5) . ?
C23 C22 1.383(4) . ?
C23 H23 0.9300 . ?
C28 C29 1.378(5) . ?
C28 C33 1.385(4) . ?
C6 C5 1.331(5) . ?
C6 C7 1.434(5) . ?
C6 H6 0.9300 . ?
C3 C2 1.357(5) . ?
C3 H3 0.9300 . ?
C18 C17 1.369(5) . ?
C18 C19 1.388(5) . ?
C18 H18 0.9300 . ?
C5 H5 0.9300 . ?
C8 C9 1.358(5) . ?
C8 C7 1.400(5) . ?
C8 H8 0.9300 . ?
C29 C30 1.389(5) . ?
C29 H29 0.9300 . ?
C32 C31 1.369(6) . ?
C32 C33 1.383(5) . ?
C32 H32 0.9300 . ?
C15 H15 0.9300 . ?
C10 C9 1.395(5) . ?
C10 H10 0.9300 . ?
C33 H33 0.9300 . ?
C24 C25 1.373(5) . ?
C26 C25 1.379(5) . ?
C26 H26 0.9300 . ?
C22 H22 0.9300 . ?
C9 H9 0.9300 . ?
C2 H2 0.9300 . ?
C19 H19 0.9300 . ?
C25 H25 0.9300 . ?
C31 C30 1.358(6) . ?
C30 H30 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 Yb1 O6 79.23(8) . . ?
O4 Yb1 O3 124.00(8) . . ?
O6 Yb1 O3 78.06(8) . . ?
O4 Yb1 O5 76.31(9) . . ?
O6 Yb1 O5 124.84(8) . . ?
O3 Yb1 O5 76.22(8) . . ?
O4 Yb1 O1 132.40(8) . . ?
O6 Yb1 O1 146.21(8) . . ?
O3 Yb1 O1 89.05(8) . . ?
O5 Yb1 O1 80.73(8) . . ?
O4 Yb1 O2 78.95(8) . . ?
O6 Yb1 O2 145.38(8) . . ?
O3 Yb1 O2 136.56(8) . . ?
O5 Yb1 O2 74.84(8) . . ?
O1 Yb1 O2 54.85(8) . . ?
O4 Yb1 N2 84.49(9) . . ?
O6 Yb1 N2 80.70(8) . . ?
O3 Yb1 N2 139.60(8) . . ?
O5 Yb1 N2 143.14(8) . . ?
O1 Yb1 N2 89.92(8) . . ?
O2 Yb1 N2 70.73(8) . . ?
O4 Yb1 N1 140.03(8) . . ?
O6 Yb1 N1 71.71(8) . . ?
O3 Yb1 N1 76.31(7) . . ?
O5 Yb1 N1 143.30(8) . . ?
O1 Yb1 N1 74.94(7) . . ?
O2 Yb1 N1 110.85(7) . . ?
N2 Yb1 N1 64.49(8) . . ?
O4 Yb1 C13 105.05(9) . . ?
O6 Yb1 C13 160.82(9) . . ?
O3 Yb1 C13 112.76(9) . . ?
O5 Yb1 C13 74.08(8) . . ?
O1 Yb1 C13 27.77(9) . . ?
O2 Yb1 C13 27.24(8) . . ?
N2 Yb1 C13 81.13(8) . . ?
N1 Yb1 C13 94.86(8) . . ?
O4 Yb1 Yb1 55.65(6) . 2_655 ?
O6 Yb1 Yb1 64.10(6) . 2_655 ?
O3 Yb1 Yb1 68.37(6) . 2_655 ?
O5 Yb1 Yb1 61.20(6) . 2_655 ?
O1 Yb1 Yb1 138.90(6) . 2_655 ?
O2 Yb1 Yb1 121.53(5) . 2_655 ?
N2 Yb1 Yb1 129.68(6) . 2_655 ?
N1 Yb1 Yb1 127.54(5) . 2_655 ?
C13 Yb1 Yb1 133.90(6) . 2_655 ?
O2 C13 O1 120.7(3) . . ?
O2 C13 C14 120.5(3) . . ?
O1 C13 C14 118.8(3) . . ?
O2 C13 Yb1 63.76(16) . . ?
O1 C13 Yb1 57.49(15) . . ?
C14 C13 Yb1 170.2(2) . . ?
C13 O2 Yb1 89.00(19) . . ?
C20 O3 Yb1 131.6(2) . . ?
C13 O1 Yb1 94.75(19) . . ?
C10 N2 C11 117.7(3) . . ?
C10 N2 Yb1 121.1(2) . . ?
C11 N2 Yb1 121.12(19) . . ?
C27 O5 Yb1 137.9(2) . . ?
C20 O4 Yb1 158.2(2) 2_655 . ?
C27 O6 Yb1 137.9(2) 2_655 . ?
O3 C20 O4 125.0(3) . 2_655 ?
O3 C20 C21 118.2(3) . . ?
O4 C20 C21 116.8(3) 2_655 . ?
C17 C16 C15 118.7(3) . . ?
C17 C16 H16 120.6 . . ?
C15 C16 H16 120.6 . . ?
C1 N1 C12 117.2(3) . . ?
C1 N1 Yb1 124.6(2) . . ?
C12 N1 Yb1 118.13(18) . . ?
C15 C14 C19 119.5(3) . . ?
C15 C14 C13 120.9(3) . . ?
C19 C14 C13 119.5(3) . . ?
C3 C4 C12 117.7(3) . . ?
C3 C4 C5 122.9(3) . . ?
C12 C4 C5 119.3(3) . . ?
C22 C21 C26 119.1(3) . . ?
C22 C21 C20 120.6(3) . . ?
C26 C21 C20 120.3(3) . . ?
N2 C11 C7 122.8(3) . . ?
N2 C11 C12 117.9(3) . . ?
C7 C11 C12 119.3(3) . . ?
N1 C1 C2 123.6(3) . . ?
N1 C1 H1 118.2 . . ?
C2 C1 H1 118.2 . . ?
O5 C27 O6 125.0(3) . 2_655 ?
O5 C27 C28 118.2(3) . . ?
O6 C27 C28 116.8(3) 2_655 . ?
N1 C12 C4 122.7(3) . . ?
N1 C12 C11 118.1(3) . . ?
C4 C12 C11 119.2(3) . . ?
C24 C23 C22 119.2(3) . . ?
C24 C23 H23 120.4 . . ?
C22 C23 H23 120.4 . . ?
C29 C28 C33 119.3(3) . . ?
C29 C28 C27 120.1(3) . . ?
C33 C28 C27 120.5(3) . . ?
C5 C6 C7 120.8(3) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C2 C3 C4 120.1(3) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C17 C18 C19 118.9(4) . . ?
C17 C18 H18 120.5 . . ?
C19 C18 H18 120.5 . . ?
C6 C5 C4 121.6(3) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C9 C8 C7 119.7(3) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C28 C29 C30 120.4(4) . . ?
C28 C29 H29 119.8 . . ?
C30 C29 H29 119.8 . . ?
C31 C32 C33 119.4(4) . . ?
C31 C32 H32 120.3 . . ?
C33 C32 H32 120.3 . . ?
C18 C17 C16 121.8(3) . . ?
C18 C17 Cl1 119.7(3) . . ?
C16 C17 Cl1 118.5(3) . . ?
C14 C15 C16 120.7(3) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
N2 C10 C9 122.7(3) . . ?
N2 C10 H10 118.6 . . ?
C9 C10 H10 118.6 . . ?
C32 C33 C28 120.1(4) . . ?
C32 C33 H33 120.0 . . ?
C28 C33 H33 120.0 . . ?
C23 C24 C25 121.2(3) . . ?
C23 C24 Cl2 119.3(3) . . ?
C25 C24 Cl2 119.5(3) . . ?
C25 C26 C21 120.5(3) . . ?
C25 C26 H26 119.8 . . ?
C21 C26 H26 119.8 . . ?
C21 C22 C23 120.6(3) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C8 C9 C10 119.7(3) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C3 C2 C1 118.7(3) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C18 C19 C14 120.4(4) . . ?
C18 C19 H19 119.8 . . ?
C14 C19 H19 119.8 . . ?
C24 C25 C26 119.4(3) . . ?
C24 C25 H25 120.3 . . ?
C26 C25 H25 120.3 . . ?
C8 C7 C11 117.3(3) . . ?
C8 C7 C6 123.1(3) . . ?
C11 C7 C6 119.6(3) . . ?
C30 C31 C32 121.6(4) . . ?
C30 C31 Cl3 119.8(3) . . ?
C32 C31 Cl3 118.6(3) . . ?
C31 C30 C29 119.3(4) . . ?
C31 C30 H30 120.4 . . ?
C29 C30 H30 120.4 . . ?

_refine_diff_density_max         0.666
_refine_diff_density_min         -0.543
_refine_diff_density_rms         0.103

_shelxl_version_number           2013-4

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_h-m   'P -1'
_symmetry_int_tables_number      2
_chemical_absolute_configuration ?
_database_code_depnum_ccdc_archive 'CCDC 1018746'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_Compound_10


_audit_creation_method           SHELXL-2013
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C66 H40 Cl6 Lu2 N4 O12'
_chemical_melting_point          ?

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colorless

_diffrn_ambient_temperature      293(2)
_chemical_formula_weight         1643.66

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

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

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

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

_cell_length_a                   10.1082(5)
_cell_length_b                   11.7926(5)
_cell_length_c                   14.2440(7)
_cell_angle_alpha                111.419(3)
_cell_angle_beta                 96.559(3)
_cell_angle_gamma                101.088(2)
_cell_volume                     1519.19(13)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    21080
_cell_measurement_theta_min      4.702
_cell_measurement_theta_max      40.334
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.797
_exptl_crystal_F_000             804
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    3.562
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6741
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS, Bruker-AXS (2008)'

_exptl_special_details           
;
 ?
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21078
_diffrn_reflns_av_unetI/netI     0.0818
_diffrn_reflns_av_R_equivalents  0.0653
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.568
_diffrn_reflns_theta_max         28.052
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7367
_reflns_number_gt                5578
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX, Bruker-AXS'
_computing_cell_refinement       'SAINT, Bruker-AXS'
_computing_data_reduction        'SAINT, Bruker-AXS'
_computing_structure_solution    'SIR92 (Gualardi, 1994)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Crystal Maker (Palmer, 2009)'
_computing_publication_material  'WINGX (Farrugia, 2012)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0174P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7367
_refine_ls_number_parameters     406
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0407
_refine_ls_wR_factor_ref         0.0661
_refine_ls_wR_factor_gt          0.0588
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_restrained_S_all      0.986
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Lu1 Lu 0.37838(2) 0.12888(2) 0.56466(2) 0.02654(6) Uani 1 1 d . . . . .
Cl1 Cl 0.13514(17) 0.31175(16) 1.15729(11) 0.0728(5) Uani 1 1 d . . . . .
Cl2 Cl 1.18809(17) 0.57646(15) 0.90857(13) 0.0872(6) Uani 1 1 d . . . . .
Cl3 Cl 0.7867(2) 0.08203(19) 1.09797(13) 0.1077(7) Uani 1 1 d . . . . .
O2 O 0.4286(4) 0.2630(3) 0.7488(2) 0.0429(9) Uani 1 1 d . . . . .
O5 O 0.4301(3) 0.0036(3) 0.6448(2) 0.0425(8) Uani 1 1 d . . . . .
O1 O 0.2184(3) 0.1497(3) 0.6693(2) 0.0381(8) Uani 1 1 d . . . . .
O4 O 0.6078(3) 0.1781(3) 0.5991(2) 0.0461(9) Uani 1 1 d . . . . .
C25 C 1.0741(5) 0.3896(5) 0.7234(4) 0.0458(13) Uani 1 1 d . . . . .
H25 H 1.1588 0.4099 0.7060 0.055 Uiso 1 1 calc R U . . .
N2 N 0.4095(4) 0.3532(3) 0.5879(3) 0.0318(9) Uani 1 1 d . . . . .
O6 O 0.4225(3) 0.1126(3) 0.4087(2) 0.0414(8) Uani 1 1 d . . . . .
O3 O 0.2445(3) -0.0651(3) 0.4604(2) 0.0399(8) Uani 1 1 d . . . . .
C14 C 0.2617(5) 0.2478(4) 0.8524(4) 0.0361(11) Uani 1 1 d . . . . .
C20 C 0.7265(5) 0.1616(4) 0.5988(4) 0.0319(11) Uani 1 1 d . . . . .
N1 N 0.1779(4) 0.1750(3) 0.4678(3) 0.0295(9) Uani 1 1 d . . . . .
C12 C 0.1927(5) 0.2936(4) 0.4721(3) 0.0280(10) Uani 1 1 d . . . . .
C28 C 0.5893(5) -0.0149(4) 0.7705(4) 0.0337(11) Uani 1 1 d . . . . .
C11 C 0.3138(5) 0.3884(4) 0.5366(3) 0.0289(10) Uani 1 1 d . . . . .
C13 C 0.3067(5) 0.2205(4) 0.7514(4) 0.0343(12) Uani 1 1 d . . . . .
C27 C 0.5265(5) -0.0434(4) 0.6608(4) 0.0318(11) Uani 1 1 d . . . . .
C1 C 0.0621(5) 0.0906(4) 0.4118(3) 0.0362(12) Uani 1 1 d . . . . .
H1 H 0.0496 0.0096 0.4101 0.043 Uiso 1 1 calc R U . . .
C21 C 0.8417(4) 0.2649(4) 0.6764(3) 0.0284(10) Uani 1 1 d . . . . .
C5 C 0.1160(6) 0.4548(5) 0.4251(4) 0.0506(15) Uani 1 1 d . . . . .
H5 H 0.0520 0.4763 0.3867 0.061 Uiso 1 1 calc R U . . .
C3 C -0.0256(5) 0.2338(5) 0.3568(4) 0.0464(14) Uani 1 1 d . . . . .
H3 H -0.0930 0.2526 0.3191 0.056 Uiso 1 1 calc R U . . .
C15 C 0.1273(5) 0.2046(5) 0.8569(4) 0.0453(13) Uani 1 1 d . . . . .
H15 H 0.0620 0.1603 0.7961 0.054 Uiso 1 1 calc R U . . .
C17 C 0.1839(6) 0.2896(5) 1.0386(4) 0.0526(15) Uani 1 1 d . . . . .
C16 C 0.0875(6) 0.2257(5) 0.9502(4) 0.0483(14) Uani 1 1 d . . . . .
H16 H -0.0039 0.1967 0.9524 0.058 Uiso 1 1 calc R U . . .
C4 C 0.0945(5) 0.3269(4) 0.4159(3) 0.0344(11) Uani 1 1 d . . . . .
C7 C 0.3292(5) 0.5148(4) 0.5468(4) 0.0379(12) Uani 1 1 d . . . . .
C18 C 0.3189(6) 0.3373(6) 1.0378(4) 0.0607(17) Uani 1 1 d . . . . .
H18 H 0.3829 0.3830 1.0992 0.073 Uiso 1 1 calc R U . . .
C29 C 0.5408(6) 0.0611(5) 0.8507(4) 0.0529(15) Uani 1 1 d . . . . .
H29 H 0.4667 0.0927 0.8370 0.064 Uiso 1 1 calc R U . . .
C26 C 0.9696(5) 0.2925(4) 0.6522(4) 0.0374(12) Uani 1 1 d . . . . .
H26 H 0.9851 0.2454 0.5880 0.045 Uiso 1 1 calc R U . . .
C22 C 0.8219(5) 0.3337(5) 0.7732(4) 0.0456(13) Uani 1 1 d . . . . .
H22 H 0.7363 0.3166 0.7903 0.055 Uiso 1 1 calc R U . . .
C10 C 0.5172(5) 0.4424(4) 0.6518(4) 0.0408(12) Uani 1 1 d . . . . .
H10 H 0.5822 0.4194 0.6880 0.049 Uiso 1 1 calc R U . . .
C8 C 0.4448(6) 0.6043(5) 0.6150(4) 0.0487(14) Uani 1 1 d . . . . .
H8 H 0.4581 0.6884 0.6247 0.058 Uiso 1 1 calc R U . . .
C6 C 0.2272(6) 0.5439(5) 0.4884(4) 0.0512(15) Uani 1 1 d . . . . .
H6 H 0.2377 0.6264 0.4941 0.061 Uiso 1 1 calc R U . . .
C33 C 0.7020(5) -0.0572(5) 0.7930(4) 0.0506(14) Uani 1 1 d . . . . .
H33 H 0.7377 -0.1062 0.7395 0.061 Uiso 1 1 calc R U . . .
C31 C 0.7104(7) 0.0460(6) 0.9723(4) 0.0627(17) Uani 1 1 d . . . . .
C30 C 0.6021(7) 0.0905(5) 0.9516(4) 0.0653(18) Uani 1 1 d . . . . .
H30 H 0.5684 0.1412 1.0054 0.078 Uiso 1 1 calc R U . . .
C19 C 0.3582(6) 0.3159(5) 0.9435(4) 0.0537(15) Uani 1 1 d . . . . .
H19 H 0.4491 0.3473 0.9415 0.064 Uiso 1 1 calc R U . . .
C2 C -0.0427(5) 0.1155(5) 0.3551(4) 0.0450(13) Uani 1 1 d . . . . .
H2 H -0.1221 0.0528 0.3171 0.054 Uiso 1 1 calc R U . . .
C24 C 1.0546(5) 0.4558(5) 0.8184(4) 0.0497(15) Uani 1 1 d . . . . .
C9 C 0.5382(6) 0.5685(5) 0.6676(4) 0.0523(15) Uani 1 1 d . . . . .
H9 H 0.6153 0.6278 0.7136 0.063 Uiso 1 1 calc R U . . .
C23 C 0.9297(6) 0.4284(5) 0.8450(4) 0.0553(15) Uani 1 1 d . . . . .
H23 H 0.9174 0.4731 0.9109 0.066 Uiso 1 1 calc R U . . .
C32 C 0.7630(6) -0.0277(6) 0.8940(5) 0.0679(18) Uani 1 1 d . . . . .
H32 H 0.8383 -0.0574 0.9086 0.081 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Lu1 O4 2.230(3) . ?
Lu1 O6 2.263(3) . ?
Lu1 O3 2.267(3) . ?
Lu1 O5 2.269(3) . ?
Lu1 O1 2.309(3) . ?
Lu1 O2 2.449(3) . ?
Lu1 N2 2.495(3) . ?
Lu1 N1 2.577(3) . ?
Lu1 C13 2.722(5) . ?
Cl1 C17 1.757(5) . ?
Cl2 C24 1.739(5) . ?
Cl3 C31 1.727(6) . ?
O2 C13 1.248(5) . ?
O5 C27 1.248(5) . ?
O1 C13 1.274(5) . ?
O4 C20 1.252(5) . ?
C25 C24 1.351(7) . ?
C25 C26 1.378(6) . ?
C25 H25 0.9300 . ?
N2 C10 1.324(5) . ?
N2 C11 1.363(5) . ?
O6 C27 1.265(5) 2_656 ?
O3 C20 1.255(5) 2_656 ?
C14 C15 1.373(6) . ?
C14 C19 1.389(6) . ?
C14 C13 1.499(6) . ?
C20 O3 1.255(5) 2_656 ?
C20 C21 1.496(6) . ?
N1 C1 1.325(5) . ?
N1 C12 1.354(5) . ?
C12 C4 1.407(6) . ?
C12 C11 1.435(6) . ?
C28 C29 1.377(6) . ?
C28 C33 1.378(6) . ?
C28 C27 1.505(6) . ?
C11 C7 1.419(6) . ?
C27 O6 1.265(5) 2_656 ?
C1 C2 1.399(6) . ?
C1 H1 0.9300 . ?
C21 C22 1.382(6) . ?
C21 C26 1.385(6) . ?
C5 C6 1.342(7) . ?
C5 C4 1.437(6) . ?
C5 H5 0.9300 . ?
C3 C2 1.363(6) . ?
C3 C4 1.402(6) . ?
C3 H3 0.9300 . ?
C15 C16 1.381(6) . ?
C15 H15 0.9300 . ?
C17 C16 1.360(7) . ?
C17 C18 1.376(7) . ?
C16 H16 0.9300 . ?
C7 C8 1.393(7) . ?
C7 C6 1.423(6) . ?
C18 C19 1.392(7) . ?
C18 H18 0.9300 . ?
C29 C30 1.386(7) . ?
C29 H29 0.9300 . ?
C26 H26 0.9300 . ?
C22 C23 1.386(6) . ?
C22 H22 0.9300 . ?
C10 C9 1.390(6) . ?
C10 H10 0.9300 . ?
C8 C9 1.361(7) . ?
C8 H8 0.9300 . ?
C6 H6 0.9300 . ?
C33 C32 1.387(7) . ?
C33 H33 0.9300 . ?
C31 C30 1.350(8) . ?
C31 C32 1.373(8) . ?
C30 H30 0.9300 . ?
C19 H19 0.9300 . ?
C2 H2 0.9300 . ?
C24 C23 1.373(7) . ?
C9 H9 0.9300 . ?
C23 H23 0.9300 . ?
C32 H32 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 Lu1 O6 79.29(11) . . ?
O4 Lu1 O3 124.05(11) . . ?
O6 Lu1 O3 78.14(11) . . ?
O4 Lu1 O5 76.19(12) . . ?
O6 Lu1 O5 124.62(11) . . ?
O3 Lu1 O5 76.07(11) . . ?
O4 Lu1 O1 132.35(11) . . ?
O6 Lu1 O1 146.23(11) . . ?
O3 Lu1 O1 88.92(12) . . ?
O5 Lu1 O1 80.86(11) . . ?
O4 Lu1 O2 78.84(11) . . ?
O6 Lu1 O2 145.37(11) . . ?
O3 Lu1 O2 136.49(11) . . ?
O5 Lu1 O2 74.98(11) . . ?
O1 Lu1 O2 54.94(11) . . ?
O4 Lu1 N2 84.21(12) . . ?
O6 Lu1 N2 80.70(11) . . ?
O3 Lu1 N2 139.90(12) . . ?
O5 Lu1 N2 143.08(12) . . ?
O1 Lu1 N2 90.17(11) . . ?
O2 Lu1 N2 70.67(11) . . ?
O4 Lu1 N1 140.05(12) . . ?
O6 Lu1 N1 71.64(11) . . ?
O3 Lu1 N1 76.30(11) . . ?
O5 Lu1 N1 143.37(12) . . ?
O1 Lu1 N1 75.04(11) . . ?
O2 Lu1 N1 110.99(11) . . ?
N2 Lu1 N1 64.81(12) . . ?
O4 Lu1 C13 104.98(14) . . ?
O6 Lu1 C13 160.80(12) . . ?
O3 Lu1 C13 112.71(14) . . ?
O5 Lu1 C13 74.32(12) . . ?
O1 Lu1 C13 27.81(12) . . ?
O2 Lu1 C13 27.27(12) . . ?
N2 Lu1 C13 81.14(12) . . ?
N1 Lu1 C13 94.92(12) . . ?
C13 O2 Lu1 88.7(3) . . ?
C27 O5 Lu1 138.9(3) . . ?
C13 O1 Lu1 94.4(3) . . ?
C20 O4 Lu1 158.1(3) . . ?
C24 C25 C26 120.6(5) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
C10 N2 C11 117.7(4) . . ?
C10 N2 Lu1 121.5(3) . . ?
C11 N2 Lu1 120.7(3) . . ?
C27 O6 Lu1 137.9(3) 2_656 . ?
C20 O3 Lu1 131.6(3) 2_656 . ?
C15 C14 C19 119.1(5) . . ?
C15 C14 C13 121.4(4) . . ?
C19 C14 C13 119.5(5) . . ?
O4 C20 O3 125.2(4) . 2_656 ?
O4 C20 C21 116.8(4) . . ?
O3 C20 C21 118.0(4) 2_656 . ?
C1 N1 C12 117.2(4) . . ?
C1 N1 Lu1 124.9(3) . . ?
C12 N1 Lu1 117.9(3) . . ?
N1 C12 C4 122.6(4) . . ?
N1 C12 C11 118.4(4) . . ?
C4 C12 C11 119.0(4) . . ?
C29 C28 C33 118.7(5) . . ?
C29 C28 C27 120.4(4) . . ?
C33 C28 C27 120.8(4) . . ?
N2 C11 C7 122.2(4) . . ?
N2 C11 C12 118.0(4) . . ?
C7 C11 C12 119.8(4) . . ?
O2 C13 O1 121.3(4) . . ?
O2 C13 C14 120.5(4) . . ?
O1 C13 C14 118.1(5) . . ?
O2 C13 Lu1 64.1(3) . . ?
O1 C13 Lu1 57.7(2) . . ?
C14 C13 Lu1 170.1(3) . . ?
O5 C27 O6 124.8(4) . 2_656 ?
O5 C27 C28 118.4(4) . . ?
O6 C27 C28 116.8(4) 2_656 . ?
N1 C1 C2 124.2(4) . . ?
N1 C1 H1 117.9 . . ?
C2 C1 H1 117.9 . . ?
C22 C21 C26 119.1(4) . . ?
C22 C21 C20 120.4(4) . . ?
C26 C21 C20 120.5(4) . . ?
C6 C5 C4 121.0(5) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C2 C3 C4 119.5(5) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C14 C15 C16 121.1(5) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C16 C17 C18 121.8(5) . . ?
C16 C17 Cl1 119.2(5) . . ?
C18 C17 Cl1 119.0(4) . . ?
C17 C16 C15 119.0(5) . . ?
C17 C16 H16 120.5 . . ?
C15 C16 H16 120.5 . . ?
C3 C4 C12 117.9(4) . . ?
C3 C4 C5 122.4(5) . . ?
C12 C4 C5 119.7(5) . . ?
C8 C7 C11 117.4(4) . . ?
C8 C7 C6 123.5(5) . . ?
C11 C7 C6 119.1(5) . . ?
C17 C18 C19 118.8(5) . . ?
C17 C18 H18 120.6 . . ?
C19 C18 H18 120.6 . . ?
C28 C29 C30 120.1(5) . . ?
C28 C29 H29 119.9 . . ?
C30 C29 H29 119.9 . . ?
C25 C26 C21 120.0(5) . . ?
C25 C26 H26 120.0 . . ?
C21 C26 H26 120.0 . . ?
C21 C22 C23 120.0(5) . . ?
C21 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?
N2 C10 C9 123.5(5) . . ?
N2 C10 H10 118.3 . . ?
C9 C10 H10 118.3 . . ?
C9 C8 C7 119.8(5) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C5 C6 C7 121.4(5) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C28 C33 C32 121.0(5) . . ?
C28 C33 H33 119.5 . . ?
C32 C33 H33 119.5 . . ?
C30 C31 C32 120.8(5) . . ?
C30 C31 Cl3 120.5(5) . . ?
C32 C31 Cl3 118.7(5) . . ?
C31 C30 C29 120.4(6) . . ?
C31 C30 H30 119.8 . . ?
C29 C30 H30 119.8 . . ?
C14 C19 C18 120.0(5) . . ?
C14 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C3 C2 C1 118.5(5) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C25 C24 C23 120.5(5) . . ?
C25 C24 Cl2 120.3(4) . . ?
C23 C24 Cl2 119.2(5) . . ?
C8 C9 C10 119.3(5) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
C24 C23 C22 119.7(5) . . ?
C24 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C31 C32 C33 119.0(6) . . ?
C31 C32 H32 120.5 . . ?
C33 C32 H32 120.5 . . ?

_refine_diff_density_max         0.956
_refine_diff_density_min         -1.069
_refine_diff_density_rms         0.146

_shelxl_version_number           2013-4

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_h-m   'P -1'
_symmetry_int_tables_number      2
_chemical_absolute_configuration ?
_database_code_depnum_ccdc_archive 'CCDC 1018747'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_Compound_11


_audit_creation_method           SHELXL-2013
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C66 H40 Cl6 N4 O12 Y2'
_chemical_melting_point          ?

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colorless

_diffrn_ambient_temperature      293(2)
_chemical_formula_weight         1471.54

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Y Y -2.7962 3.5667 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   10.0929(8)
_cell_length_b                   11.8472(9)
_cell_length_c                   14.2880(11)
_cell_angle_alpha                111.160(3)
_cell_angle_beta                 96.429(4)
_cell_angle_gamma                101.497(4)
_cell_volume                     1529.3(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    19695
_cell_measurement_theta_min      4.705
_cell_measurement_theta_max      44.368
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.598
_exptl_crystal_F_000             740
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.07
_exptl_absorpt_coefficient_mu    2.218
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6688
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   'SADABS, Bruker-AXS (2008)'

_exptl_special_details           
;
 ?
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19695
_diffrn_reflns_av_unetI/netI     0.0664
_diffrn_reflns_av_R_equivalents  0.0534
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.560
_diffrn_reflns_theta_max         27.051
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6696
_reflns_number_gt                4980
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX, Bruker-AXS'
_computing_cell_refinement       'SAINT, Bruker-AXS'
_computing_data_reduction        'SAINT, Bruker-AXS'
_computing_structure_solution    'SIR92 (Gualardi, 1994)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Crystal Maker (Palmer, 2009)'
_computing_publication_material  'WINGX (Farrugia, 2012)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0295P)²+0.2262P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6696
_refine_ls_number_parameters     406
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0696
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.0830
_refine_ls_wR_factor_gt          0.0744
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Y1 Y 0.87708(3) 0.62819(3) 0.06492(2) 0.02585(9) Uani 1 1 d . . . . .
Cl1 Cl 0.63696(11) 0.81262(10) 0.65846(7) 0.0712(3) Uani 1 1 d . . . . .
Cl2 Cl 0.31063(11) -0.07863(10) -0.41059(9) 0.0861(4) Uani 1 1 d . . . . .
Cl3 Cl 0.71137(15) 0.41901(12) -0.59698(8) 0.1036(5) Uani 1 1 d . . . . .
O3 O 0.7389(2) 0.43177(18) -0.04157(16) 0.0409(5) Uani 1 1 d . . . . .
O1 O 0.7152(2) 0.65037(19) 0.17143(15) 0.0386(5) Uani 1 1 d . . . . .
O2 O 0.9268(2) 0.76285(18) 0.24954(15) 0.0407(5) Uani 1 1 d . . . . .
O6 O 0.9241(2) 0.61319(19) -0.09277(15) 0.0402(5) Uani 1 1 d . . . . .
O5 O 0.9280(2) 0.50088(19) 0.14612(15) 0.0424(5) Uani 1 1 d . . . . .
O4 O 1.1110(2) 0.6766(2) 0.09946(16) 0.0468(6) Uani 1 1 d . . . . .
N1 N 0.6752(2) 0.6769(2) -0.03302(17) 0.0276(5) Uani 1 1 d . . . . .
N2 N 0.9067(2) 0.8555(2) 0.08794(18) 0.0312(6) Uani 1 1 d . . . . .
C14 C 0.7610(3) 0.7474(3) 0.3541(2) 0.0356(7) Uani 1 1 d . . . . .
C20 C 0.7695(3) 0.3370(3) -0.1003(2) 0.0327(7) Uani 1 1 d . . . . .
C12 C 0.6912(3) 0.7955(3) -0.0295(2) 0.0285(6) Uani 1 1 d . . . . .
C11 C 0.8124(3) 0.8905(3) 0.0365(2) 0.0290(7) Uani 1 1 d . . . . .
C27 C 0.9734(3) 0.5439(3) -0.1619(2) 0.0305(7) Uani 1 1 d . . . . .
C28 C 0.9099(3) 0.5148(3) -0.2710(2) 0.0346(7) Uani 1 1 d . . . . .
C21 C 0.6547(3) 0.2336(3) -0.1777(2) 0.0296(7) Uani 1 1 d . . . . .
C4 C 0.5925(3) 0.8290(3) -0.0851(2) 0.0358(7) Uani 1 1 d . . . . .
C33 C 0.7982(3) 0.5585(3) -0.2931(3) 0.0489(9) Uani 1 1 d . . . . .
H33 H 0.7640 0.6087 -0.2399 0.059 Uiso 1 1 calc R U . . .
C13 C 0.8038(3) 0.7202(3) 0.2529(2) 0.0342(7) Uani 1 1 d . . . . .
C6 C 0.7254(4) 1.0446(3) -0.0137(3) 0.0486(9) Uani 1 1 d . . . . .
H6 H 0.7364 1.1265 -0.0087 0.058 Uiso 1 1 calc R U . . .
C3 C 0.4734(3) 0.7353(3) -0.1442(2) 0.0457(8) Uani 1 1 d . . . . .
H3 H 0.4060 0.7534 -0.1824 0.055 Uiso 1 1 calc R U . . .
C22 C 0.5258(3) 0.2058(3) -0.1550(2) 0.0337(7) Uani 1 1 d . . . . .
H22 H 0.5096 0.2533 -0.0916 0.040 Uiso 1 1 calc R U . . .
C29 C 0.9580(4) 0.4392(3) -0.3510(2) 0.0514(9) Uani 1 1 d . . . . .
H29 H 1.0322 0.4082 -0.3372 0.062 Uiso 1 1 calc R U . . .
C1 C 0.5590(3) 0.5924(3) -0.0899(2) 0.0352(7) Uani 1 1 d . . . . .
H1 H 0.5459 0.5113 -0.0924 0.042 Uiso 1 1 calc R U . . .
C7 C 0.8274(3) 1.0156(3) 0.0465(2) 0.0375(7) Uani 1 1 d . . . . .
C26 C 0.6766(3) 0.1652(3) -0.2736(2) 0.0438(8) Uani 1 1 d . . . . .
H26 H 0.7630 0.1827 -0.2897 0.053 Uiso 1 1 calc R U . . .
C8 C 0.9435(4) 1.1055(3) 0.1143(3) 0.0489(9) Uani 1 1 d . . . . .
H8 H 0.9573 1.1889 0.1229 0.059 Uiso 1 1 calc R U . . .
C17 C 0.6852(4) 0.7904(3) 0.5408(3) 0.0492(9) Uani 1 1 d . . . . .
C10 C 1.0146(3) 0.9448(3) 0.1515(2) 0.0411(8) Uani 1 1 d . . . . .
H10 H 1.0798 0.9220 0.1874 0.049 Uiso 1 1 calc R U . . .
C16 C 0.5870(4) 0.7261(3) 0.4529(3) 0.0499(9) Uani 1 1 d . . . . .
H16 H 0.4957 0.6971 0.4562 0.060 Uiso 1 1 calc R U . . .
C24 C 0.4429(3) 0.0425(3) -0.3204(3) 0.0472(9) Uani 1 1 d . . . . .
C2 C 0.4560(3) 0.6183(3) -0.1459(2) 0.0442(8) Uani 1 1 d . . . . .
H2 H 0.3761 0.5560 -0.1839 0.053 Uiso 1 1 calc R U . . .
C19 C 0.8572(4) 0.8153(3) 0.4442(3) 0.0513(9) Uani 1 1 d . . . . .
H19 H 0.9482 0.8470 0.4418 0.062 Uiso 1 1 calc R U . . .
C23 C 0.4206(3) 0.1082(3) -0.2253(3) 0.0415(8) Uani 1 1 d . . . . .
H23 H 0.3354 0.0872 -0.2083 0.050 Uiso 1 1 calc R U . . .
C9 C 1.0360(4) 1.0708(3) 0.1677(3) 0.0490(9) Uani 1 1 d . . . . .
H9 H 1.1124 1.1302 0.2144 0.059 Uiso 1 1 calc R U . . .
C15 C 0.6249(3) 0.7045(3) 0.3589(2) 0.0443(8) Uani 1 1 d . . . . .
H15 H 0.5586 0.6609 0.2989 0.053 Uiso 1 1 calc R U . . .
C18 C 0.8196(4) 0.8366(4) 0.5382(3) 0.0588(10) Uani 1 1 d . . . . .
H18 H 0.8848 0.8817 0.5988 0.071 Uiso 1 1 calc R U . . .
C32 C 0.7370(4) 0.5283(3) -0.3933(3) 0.0621(11) Uani 1 1 d . . . . .
H32 H 0.6620 0.5581 -0.4077 0.074 Uiso 1 1 calc R U . . .
C31 C 0.7872(4) 0.4545(3) -0.4710(3) 0.0585(10) Uani 1 1 d . . . . .
C25 C 0.5688(4) 0.0704(3) -0.3455(3) 0.0526(9) Uani 1 1 d . . . . .
H25 H 0.5822 0.0259 -0.4107 0.063 Uiso 1 1 calc R U . . .
C5 C 0.6157(4) 0.9558(3) -0.0764(3) 0.0486(9) Uani 1 1 d . . . . .
H5 H 0.5524 0.9767 -0.1156 0.058 Uiso 1 1 calc R U . . .
C30 C 0.8975(4) 0.4092(4) -0.4511(3) 0.0641(11) Uani 1 1 d . . . . .
H30 H 0.9309 0.3587 -0.5047 0.077 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Y1 O4 2.268(2) . ?
Y1 O6 2.306(2) . ?
Y1 O5 2.3075(19) . ?
Y1 O3 2.3131(19) . ?
Y1 O1 2.3436(19) . ?
Y1 O2 2.470(2) . ?
Y1 N2 2.543(2) . ?
Y1 N1 2.618(2) . ?
Y1 C13 2.757(3) . ?
Cl1 C17 1.746(3) . ?
Cl2 C24 1.737(3) . ?
Cl3 C31 1.738(3) . ?
O3 C20 1.255(3) . ?
O1 C13 1.271(3) . ?
O2 C13 1.257(3) . ?
O6 C27 1.259(3) . ?
O5 C27 1.252(3) 2_765 ?
O4 C20 1.248(3) 2_765 ?
N1 C1 1.330(3) . ?
N1 C12 1.364(3) . ?
N2 C10 1.325(4) . ?
N2 C11 1.356(3) . ?
C14 C19 1.382(4) . ?
C14 C15 1.386(4) . ?
C14 C13 1.496(4) . ?
C20 O4 1.248(3) 2_765 ?
C20 C21 1.495(4) . ?
C12 C4 1.410(4) . ?
C12 C11 1.442(4) . ?
C11 C7 1.411(4) . ?
C27 O5 1.252(3) 2_765 ?
C27 C28 1.503(4) . ?
C28 C29 1.379(4) . ?
C28 C33 1.382(4) . ?
C21 C22 1.381(4) . ?
C21 C26 1.386(4) . ?
C4 C3 1.398(4) . ?
C4 C5 1.430(4) . ?
C33 C32 1.380(4) . ?
C33 H33 0.9300 . ?
C6 C5 1.330(4) . ?
C6 C7 1.440(4) . ?
C6 H6 0.9300 . ?
C3 C2 1.353(4) . ?
C3 H3 0.9300 . ?
C22 C23 1.381(4) . ?
C22 H22 0.9300 . ?
C29 C30 1.376(4) . ?
C29 H29 0.9300 . ?
C1 C2 1.390(4) . ?
C1 H1 0.9300 . ?
C7 C8 1.396(4) . ?
C26 C25 1.390(4) . ?
C26 H26 0.9300 . ?
C8 C9 1.358(4) . ?
C8 H8 0.9300 . ?
C17 C16 1.367(5) . ?
C17 C18 1.367(5) . ?
C10 C9 1.392(4) . ?
C10 H10 0.9300 . ?
C16 C15 1.386(4) . ?
C16 H16 0.9300 . ?
C24 C25 1.369(5) . ?
C24 C23 1.369(4) . ?
C2 H2 0.9300 . ?
C19 C18 1.385(4) . ?
C19 H19 0.9300 . ?
C23 H23 0.9300 . ?
C9 H9 0.9300 . ?
C15 H15 0.9300 . ?
C18 H18 0.9300 . ?
C32 C31 1.362(5) . ?
C32 H32 0.9300 . ?
C31 C30 1.373(5) . ?
C25 H25 0.9300 . ?
C5 H5 0.9300 . ?
C30 H30 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 Y1 O6 78.93(7) . . ?
O4 Y1 O5 76.01(8) . . ?
O6 Y1 O5 124.65(7) . . ?
O4 Y1 O3 123.77(8) . . ?
O6 Y1 O3 78.22(7) . . ?
O5 Y1 O3 76.33(7) . . ?
O4 Y1 O1 132.14(7) . . ?
O6 Y1 O1 146.67(7) . . ?
O5 Y1 O1 80.91(7) . . ?
O3 Y1 O1 89.48(7) . . ?
O4 Y1 O2 79.33(7) . . ?
O6 Y1 O2 145.06(7) . . ?
O5 Y1 O2 75.26(7) . . ?
O3 Y1 O2 136.72(7) . . ?
O1 Y1 O2 54.30(7) . . ?
O4 Y1 N2 85.42(8) . . ?
O6 Y1 N2 80.71(7) . . ?
O5 Y1 N2 143.54(8) . . ?
O3 Y1 N2 138.99(7) . . ?
O1 Y1 N2 89.23(7) . . ?
O2 Y1 N2 70.57(7) . . ?
O4 Y1 N1 139.86(7) . . ?
O6 Y1 N1 71.70(7) . . ?
O5 Y1 N1 143.74(7) . . ?
O3 Y1 N1 76.44(7) . . ?
O1 Y1 N1 75.35(7) . . ?
O2 Y1 N1 110.51(7) . . ?
N2 Y1 N1 63.63(7) . . ?
O4 Y1 C13 105.25(9) . . ?
O6 Y1 C13 160.58(7) . . ?
O5 Y1 C13 74.46(8) . . ?
O3 Y1 C13 112.91(9) . . ?
O1 Y1 C13 27.34(8) . . ?
O2 Y1 C13 27.11(8) . . ?
N2 Y1 C13 80.74(8) . . ?
N1 Y1 C13 94.82(8) . . ?
C20 O3 Y1 130.61(19) . . ?
C13 O1 Y1 94.75(17) . . ?
C13 O2 Y1 89.26(18) . . ?
C27 O6 Y1 137.77(18) . . ?
C27 O5 Y1 137.45(19) 2_765 . ?
C20 O4 Y1 159.8(2) 2_765 . ?
C1 N1 C12 117.0(2) . . ?
C1 N1 Y1 124.53(18) . . ?
C12 N1 Y1 118.43(18) . . ?
C10 N2 C11 117.3(2) . . ?
C10 N2 Y1 121.22(19) . . ?
C11 N2 Y1 121.52(18) . . ?
C19 C14 C15 119.0(3) . . ?
C19 C14 C13 120.4(3) . . ?
C15 C14 C13 120.7(3) . . ?
O4 C20 O3 124.7(3) 2_765 . ?
O4 C20 C21 117.6(3) 2_765 . ?
O3 C20 C21 117.7(3) . . ?
N1 C12 C4 122.7(3) . . ?
N1 C12 C11 118.1(2) . . ?
C4 C12 C11 119.2(3) . . ?
N2 C11 C7 122.7(3) . . ?
N2 C11 C12 118.0(2) . . ?
C7 C11 C12 119.3(3) . . ?
O5 C27 O6 124.8(3) 2_765 . ?
O5 C27 C28 118.1(3) 2_765 . ?
O6 C27 C28 117.2(3) . . ?
C29 C28 C33 118.7(3) . . ?
C29 C28 C27 120.6(3) . . ?
C33 C28 C27 120.6(3) . . ?
C22 C21 C26 119.3(3) . . ?
C22 C21 C20 120.6(3) . . ?
C26 C21 C20 120.1(3) . . ?
C3 C4 C12 117.3(3) . . ?
C3 C4 C5 123.2(3) . . ?
C12 C4 C5 119.5(3) . . ?
C32 C33 C28 120.6(3) . . ?
C32 C33 H33 119.7 . . ?
C28 C33 H33 119.7 . . ?
O2 C13 O1 121.0(3) . . ?
O2 C13 C14 120.0(3) . . ?
O1 C13 C14 119.0(3) . . ?
O2 C13 Y1 63.63(15) . . ?
O1 C13 Y1 57.91(14) . . ?
C14 C13 Y1 170.0(2) . . ?
C5 C6 C7 120.9(3) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C2 C3 C4 120.0(3) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C21 C22 C23 120.7(3) . . ?
C21 C22 H22 119.6 . . ?
C23 C22 H22 119.6 . . ?
C30 C29 C28 120.9(3) . . ?
C30 C29 H29 119.6 . . ?
C28 C29 H29 119.6 . . ?
N1 C1 C2 123.8(3) . . ?
N1 C1 H1 118.1 . . ?
C2 C1 H1 118.1 . . ?
C8 C7 C11 117.4(3) . . ?
C8 C7 C6 123.2(3) . . ?
C11 C7 C6 119.4(3) . . ?
C21 C26 C25 119.7(3) . . ?
C21 C26 H26 120.1 . . ?
C25 C26 H26 120.1 . . ?
C9 C8 C7 119.8(3) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C16 C17 C18 121.5(3) . . ?
C16 C17 Cl1 118.8(3) . . ?
C18 C17 Cl1 119.7(3) . . ?
N2 C10 C9 123.8(3) . . ?
N2 C10 H10 118.1 . . ?
C9 C10 H10 118.1 . . ?
C17 C16 C15 119.4(3) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C25 C24 C23 120.9(3) . . ?
C25 C24 Cl2 119.1(3) . . ?
C23 C24 Cl2 120.0(3) . . ?
C3 C2 C1 119.1(3) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C14 C19 C18 120.7(3) . . ?
C14 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C24 C23 C22 119.4(3) . . ?
C24 C23 H23 120.3 . . ?
C22 C23 H23 120.3 . . ?
C8 C9 C10 118.9(3) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 H9 120.5 . . ?
C16 C15 C14 120.3(3) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C17 C18 C19 119.0(3) . . ?
C17 C18 H18 120.5 . . ?
C19 C18 H18 120.5 . . ?
C31 C32 C33 119.6(3) . . ?
C31 C32 H32 120.2 . . ?
C33 C32 H32 120.2 . . ?
C32 C31 C30 121.0(3) . . ?
C32 C31 Cl3 119.3(3) . . ?
C30 C31 Cl3 119.7(3) . . ?
C24 C25 C26 119.9(3) . . ?
C24 C25 H25 120.1 . . ?
C26 C25 H25 120.1 . . ?
C6 C5 C4 121.7(3) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C31 C30 C29 119.2(3) . . ?
C31 C30 H30 120.4 . . ?
C29 C30 H30 120.4 . . ?

_refine_diff_density_max         0.342
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.069

_shelxl_version_number           2013-4

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_h-m   'P -1'
_symmetry_int_tables_number      2
_chemical_absolute_configuration ?

#===END
_database_code_depnum_ccdc_archive 'CCDC 1018748'
