# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2014

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#
#                 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
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  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_2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H13 Gd2 O14, C2 H8 N'
_chemical_formula_sum            'C27 H21 Gd2 N O14'
_chemical_formula_weight         897.95

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

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1'
_space_group_name_Hall           '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.3576(2)
_cell_length_b                   10.5283(4)
_cell_length_c                   17.4675(6)
_cell_angle_alpha                98.741(3)
_cell_angle_beta                 97.008(3)
_cell_angle_gamma                100.523(3)
_cell_volume                     1475.75(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6388
_cell_measurement_theta_min      2.8642
_cell_measurement_theta_max      28.0391

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.021
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             860
_exptl_crystal_F_000'            859.77
_exptl_absorpt_coefficient_mu    4.526
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.55995
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_exptl_special_details           
; 
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            11570
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_sigmaI/netI    0.0483
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.87
_diffrn_reflns_theta_max         25.03
_reflns_number_total             5220
_reflns_number_gt                4564
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP, Ver. 6.10, Bruker AXS Inc., 2000.'
_computing_publication_material  'SHELXTL-Bruker AXS Inc., 1998.'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0177P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5189
_refine_ls_number_parameters     400
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0262
_refine_ls_wR_factor_ref         0.0559
_refine_ls_wR_factor_gt          0.0523
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Gd1 Gd 0.03334(2) 0.18963(2) 0.236737(10) 0.01453(7) Uani 1 1 d . . .
Gd2 Gd 0.52029(2) 0.13507(2) 0.295276(11) 0.01648(7) Uani 1 1 d . . .
C1 C 0.2759(5) 0.2073(5) 0.4101(2) 0.0274(11) Uani 1 1 d . . .
C2 C 0.1841(5) 0.1962(5) 0.4784(2) 0.0221(10) Uani 1 1 d . . .
C3 C 0.2189(4) 0.1121(4) 0.5287(2) 0.0198(9) Uani 1 1 d . . .
H3 H 0.3036 0.0672 0.5219 0.024 Uiso 1 1 calc R . .
C4 C 0.1287(5) 0.0940(4) 0.5894(2) 0.0214(10) Uani 1 1 d . . .
C5 C 0.0046(5) 0.1627(5) 0.5987(3) 0.0365(13) Uani 1 1 d . . .
H5 H -0.0577 0.1506 0.6387 0.044 Uiso 1 1 calc R . .
C6 C -0.0283(6) 0.2481(6) 0.5502(3) 0.0466(15) Uani 1 1 d . . .
H6 H -0.1111 0.2947 0.5580 0.056 Uiso 1 1 calc R . .
C7 C 0.0607(5) 0.2659(5) 0.4896(3) 0.0346(12) Uani 1 1 d . . .
H7 H 0.0380 0.3241 0.4567 0.042 Uiso 1 1 calc R . .
C8 C 0.1641(5) -0.0014(5) 0.6416(2) 0.0219(10) Uani 1 1 d . . .
C9 C 0.3395(5) 0.2271(4) 0.1402(2) 0.0204(10) Uani 1 1 d . . .
C10 C 0.4163(4) 0.2024(4) 0.0682(2) 0.0196(9) Uani 1 1 d . . .
C11 C 0.3275(4) 0.1200(5) 0.0007(2) 0.0199(10) Uani 1 1 d . . .
H11 H 0.2176 0.0819 -0.0002 0.024 Uiso 1 1 calc R . .
C12 C 0.4015(5) 0.0941(5) -0.0652(2) 0.0219(10) Uani 1 1 d . . .
C13 C 0.5657(5) 0.1539(5) -0.0632(3) 0.0362(13) Uani 1 1 d . . .
H13 H 0.6157 0.1387 -0.1075 0.043 Uiso 1 1 calc R . .
C14 C 0.6543(5) 0.2347(6) 0.0033(3) 0.0434(15) Uani 1 1 d . . .
H14 H 0.7640 0.2733 0.0040 0.052 Uiso 1 1 calc R . .
C15 C 0.5803(5) 0.2590(5) 0.0692(3) 0.0327(12) Uani 1 1 d . . .
H15 H 0.6407 0.3134 0.1143 0.039 Uiso 1 1 calc R . .
C16 C 0.3132(5) 0.0014(4) -0.1369(2) 0.0218(10) Uani 1 1 d . . .
C17 C 0.0265(5) 0.4386(5) 0.1940(2) 0.0220(10) Uani 1 1 d . . .
C18 C 0.0274(5) 0.5696(4) 0.1709(2) 0.0232(10) Uani 1 1 d . . .
C19 C 0.1226(5) 0.6830(4) 0.2176(2) 0.0231(10) Uani 1 1 d . . .
H19 H 0.1844 0.6779 0.2646 0.028 Uiso 1 1 calc R . .
C20 C 0.1264(4) 0.8047(4) 0.1947(2) 0.0206(10) Uani 1 1 d . . .
C21 C 0.0330(5) 0.8121(5) 0.1248(3) 0.0301(11) Uani 1 1 d . . .
H21 H 0.0327 0.8930 0.1096 0.036 Uiso 1 1 calc R . .
C22 C -0.0598(6) 0.6981(5) 0.0775(3) 0.0385(12) Uani 1 1 d . . .
H22 H -0.1200 0.7031 0.0301 0.046 Uiso 1 1 calc R . .
C23 C -0.0642(5) 0.5780(5) 0.0997(3) 0.0326(11) Uani 1 1 d . . .
H23 H -0.1277 0.5025 0.0677 0.039 Uiso 1 1 calc R . .
C24 C 0.2405(5) 0.9223(5) 0.2424(2) 0.0220(10) Uani 1 1 d . . .
C25 C 0.7842(5) 0.3674(5) 0.3362(3) 0.0291(11) Uani 1 1 d . . .
H25 H 0.8660 0.4432 0.3506 0.028(12) Uiso 1 1 calc R . .
C26 C 0.4419(11) 0.6114(11) 0.3921(6) 0.161(6) Uani 1 1 d . . .
H26A H 0.4255 0.6984 0.3887 0.241 Uiso 1 1 calc R . .
H26B H 0.5440 0.6166 0.4254 0.241 Uiso 1 1 calc R . .
H26C H 0.3528 0.5654 0.4136 0.241 Uiso 1 1 calc R . .
C27 C 0.5389(10) 0.6114(10) 0.2609(8) 0.164(6) Uani 1 1 d . . .
H27A H 0.5023 0.5697 0.2072 0.247 Uiso 1 1 calc R . .
H27B H 0.6542 0.6129 0.2743 0.247 Uiso 1 1 calc R . .
H27C H 0.5211 0.6997 0.2678 0.247 Uiso 1 1 calc R . .
N1 N 0.4471(6) 0.5387(6) 0.3113(4) 0.090(2) Uani 1 1 d . . .
H1A H 0.4904 0.4677 0.3167 0.107 Uiso 1 1 calc R . .
H1B H 0.3428 0.5094 0.2866 0.107 Uiso 1 1 calc R . .
O1 O 0.2200(4) 0.2613(3) 0.35555(16) 0.0350(8) Uani 1 1 d . . .
O2 O 0.4028(4) 0.1604(4) 0.41014(17) 0.0382(9) Uani 1 1 d . . .
O3 O 0.0639(3) -0.0306(3) 0.68729(16) 0.0266(7) Uani 1 1 d . . .
O4 O 0.2919(3) -0.0475(3) 0.63458(16) 0.0293(8) Uani 1 1 d . . .
O5 O 0.1857(3) 0.2088(3) 0.13264(16) 0.0282(7) Uani 1 1 d . . .
O6 O 0.4337(3) 0.2649(3) 0.20630(15) 0.0245(7) Uani 1 1 d . . .
O7 O 0.1622(3) -0.0455(3) -0.14118(15) 0.0234(7) Uani 1 1 d . . .
O8 O 0.3973(3) -0.0268(3) -0.19017(16) 0.0316(8) Uani 1 1 d . . .
O9 O 0.1247(3) 0.4316(3) 0.25459(16) 0.0278(7) Uani 1 1 d . . .
O10 O -0.0704(3) 0.3399(3) 0.15591(17) 0.0279(7) Uani 1 1 d . . .
O11 O 0.3610(3) 0.9080(3) 0.28845(18) 0.0323(8) Uani 1 1 d . . .
O12 O 0.2239(3) 1.0370(3) 0.23258(16) 0.0234(7) Uani 1 1 d . . .
O13 O 0.6487(3) 0.3671(3) 0.35893(17) 0.0334(8) Uani 1 1 d . . .
O14 O 0.8142(3) 0.2707(3) 0.29500(17) 0.0287(7) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Gd1 O7 2.328(3) 2 ?
Gd1 O5 2.356(3) . ?
Gd1 O1 2.369(3) . ?
Gd1 O3 2.381(3) 2_556 ?
Gd1 O14 2.425(3) 1_455 ?
Gd1 O12 2.460(3) 1_545 ?
Gd1 O10 2.475(3) . ?
Gd1 O9 2.482(3) . ?
Gd1 C17 2.841(4) . ?
Gd2 O8 2.259(3) 2_655 ?
Gd2 O4 2.284(3) 2_656 ?
Gd2 O2 2.340(3) . ?
Gd2 O6 2.353(3) . ?
Gd2 O11 2.493(3) 1_545 ?
Gd2 O13 2.506(3) . ?
Gd2 O12 2.542(3) 1_545 ?
Gd2 O14 2.607(3) . ?
Gd2 C24 2.875(4) 1_545 ?
Gd2 C25 2.911(5) . ?
C1 O2 1.249(5) . ?
C1 O1 1.266(5) . ?
C1 C2 1.502(5) . ?
C2 C3 1.381(6) . ?
C2 C7 1.387(6) . ?
C3 C4 1.390(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.380(6) . ?
C4 C8 1.500(6) . ?
C5 C6 1.367(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.382(6) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 O3 1.256(4) . ?
C8 O4 1.262(5) . ?
C9 O5 1.252(5) . ?
C9 O6 1.278(5) . ?
C9 C10 1.491(5) . ?
C10 C15 1.388(5) . ?
C10 C11 1.390(6) . ?
C11 C12 1.387(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.395(5) . ?
C12 C16 1.485(6) . ?
C13 C14 1.371(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.384(6) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 O7 1.257(4) . ?
C16 O8 1.265(5) . ?
C17 O10 1.237(5) . ?
C17 O9 1.277(5) . ?
C17 C18 1.494(6) . ?
C18 C19 1.386(6) . ?
C18 C23 1.402(6) . ?
C19 C20 1.395(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.388(6) . ?
C20 C24 1.483(6) . ?
C21 C22 1.388(7) . ?
C21 H21 0.9300 . ?
C22 C23 1.373(7) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 O11 1.256(5) . ?
C24 O12 1.275(5) . ?
C24 Gd2 2.875(4) 1_565 ?
C25 O14 1.237(5) . ?
C25 O13 1.245(5) . ?
C25 H25 0.9300 . ?
C26 N1 1.510(10) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 N1 1.451(10) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
N1 H1A 0.9000 . ?
N1 H1B 0.9000 . ?
O3 Gd1 2.381(3) 2_556 ?
O4 Gd2 2.284(3) 2_656 ?
O7 Gd1 2.328(3) 2 ?
O8 Gd2 2.259(3) 2_655 ?
O11 Gd2 2.493(3) 1_565 ?
O12 Gd1 2.460(3) 1_565 ?
O12 Gd2 2.542(3) 1_565 ?
O14 Gd1 2.425(3) 1_655 ?

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
O7 Gd1 O5 83.83(10) 2 . ?
O7 Gd1 O1 157.60(11) 2 . ?
O5 Gd1 O1 107.74(10) . . ?
O7 Gd1 O3 80.54(10) 2 2_556 ?
O5 Gd1 O3 139.36(11) . 2_556 ?
O1 Gd1 O3 78.33(10) . 2_556 ?
O7 Gd1 O14 89.72(10) 2 1_455 ?
O5 Gd1 O14 141.97(10) . 1_455 ?
O1 Gd1 O14 92.06(11) . 1_455 ?
O3 Gd1 O14 75.35(10) 2_556 1_455 ?
O7 Gd1 O12 91.96(10) 2 1_545 ?
O5 Gd1 O12 69.04(10) . 1_545 ?
O1 Gd1 O12 75.25(11) . 1_545 ?
O3 Gd1 O12 74.25(9) 2_556 1_545 ?
O14 Gd1 O12 148.84(9) 1_455 1_545 ?
O7 Gd1 O10 77.76(10) 2 . ?
O5 Gd1 O10 70.43(10) . . ?
O1 Gd1 O10 123.87(11) . . ?
O3 Gd1 O10 140.18(9) 2_556 . ?
O14 Gd1 O10 71.58(10) 1_455 . ?
O12 Gd1 O10 138.99(9) 1_545 . ?
O7 Gd1 O9 130.17(10) 2 . ?
O5 Gd1 O9 79.02(11) . . ?
O1 Gd1 O9 71.79(10) . . ?
O3 Gd1 O9 137.96(10) 2_556 . ?
O14 Gd1 O9 76.86(10) 1_455 . ?
O12 Gd1 O9 123.47(9) 1_545 . ?
O10 Gd1 O9 52.43(9) . . ?
O7 Gd1 C17 103.48(11) 2 . ?
O5 Gd1 C17 72.12(11) . . ?
O1 Gd1 C17 98.39(12) . . ?
O3 Gd1 C17 148.15(10) 2_556 . ?
O14 Gd1 C17 73.11(10) 1_455 . ?
O12 Gd1 C17 136.13(10) 1_545 . ?
O10 Gd1 C17 25.76(10) . . ?
O9 Gd1 C17 26.69(10) . . ?
O8 Gd2 O4 84.12(11) 2_655 2_656 ?
O8 Gd2 O2 157.10(13) 2_655 . ?
O4 Gd2 O2 85.47(11) 2_656 . ?
O8 Gd2 O6 83.99(11) 2_655 . ?
O4 Gd2 O6 155.20(9) 2_656 . ?
O2 Gd2 O6 112.70(11) . . ?
O8 Gd2 O11 79.00(11) 2_655 1_545 ?
O4 Gd2 O11 79.06(10) 2_656 1_545 ?
O2 Gd2 O11 79.03(12) . 1_545 ?
O6 Gd2 O11 119.68(10) . 1_545 ?
O8 Gd2 O13 123.80(10) 2_655 . ?
O4 Gd2 O13 93.99(11) 2_656 . ?
O2 Gd2 O13 77.23(11) . . ?
O6 Gd2 O13 74.90(10) . . ?
O11 Gd2 O13 155.71(10) 1_545 . ?
O8 Gd2 O12 88.45(10) 2_655 1_545 ?
O4 Gd2 O12 130.62(10) 2_656 1_545 ?
O2 Gd2 O12 82.95(10) . 1_545 ?
O6 Gd2 O12 70.65(9) . 1_545 ?
O11 Gd2 O12 51.63(9) 1_545 1_545 ?
O13 Gd2 O12 129.24(9) . 1_545 ?
O8 Gd2 O14 76.73(10) 2_655 . ?
O4 Gd2 O14 71.36(10) 2_656 . ?
O2 Gd2 O14 118.82(11) . . ?
O6 Gd2 O14 84.75(9) . . ?
O11 Gd2 O14 143.21(10) 1_545 . ?
O13 Gd2 O14 50.32(9) . . ?
O12 Gd2 O14 152.54(9) 1_545 . ?
O8 Gd2 C24 79.35(11) 2_655 1_545 ?
O4 Gd2 C24 104.76(12) 2_656 1_545 ?
O2 Gd2 C24 83.68(11) . 1_545 ?
O6 Gd2 C24 94.32(11) . 1_545 ?
O11 Gd2 C24 25.82(11) 1_545 1_545 ?
O13 Gd2 C24 152.04(11) . 1_545 ?
O12 Gd2 C24 26.31(10) 1_545 1_545 ?
O14 Gd2 C24 156.02(10) . 1_545 ?
O8 Gd2 C25 100.41(12) 2_655 . ?
O4 Gd2 C25 81.97(12) 2_656 . ?
O2 Gd2 C25 98.26(12) . . ?
O6 Gd2 C25 78.88(11) . . ?
O11 Gd2 C25 160.98(11) 1_545 . ?
O13 Gd2 C25 25.18(10) . . ?
O12 Gd2 C25 147.19(11) 1_545 . ?
O14 Gd2 C25 25.14(10) . . ?
C24 Gd2 C25 173.17(12) 1_545 . ?
O2 C1 O1 123.7(4) . . ?
O2 C1 C2 117.5(4) . . ?
O1 C1 C2 118.8(4) . . ?
C3 C2 C7 119.7(3) . . ?
C3 C2 C1 119.7(4) . . ?
C7 C2 C1 120.5(4) . . ?
C2 C3 C4 120.8(4) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 118.5(4) . . ?
C5 C4 C8 121.4(3) . . ?
C3 C4 C8 120.0(4) . . ?
C6 C5 C4 121.1(4) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C7 120.5(4) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C6 C7 C2 119.4(4) . . ?
C6 C7 H7 120.3 . . ?
C2 C7 H7 120.3 . . ?
O3 C8 O4 125.5(4) . . ?
O3 C8 C4 117.9(3) . . ?
O4 C8 C4 116.6(3) . . ?
O5 C9 O6 123.6(3) . . ?
O5 C9 C10 118.0(3) . . ?
O6 C9 C10 118.4(3) . . ?
C15 C10 C11 119.5(3) . . ?
C15 C10 C9 119.6(4) . . ?
C11 C10 C9 120.9(3) . . ?
C12 C11 C10 120.5(3) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C13 118.9(4) . . ?
C11 C12 C16 122.1(4) . . ?
C13 C12 C16 118.9(3) . . ?
C14 C13 C12 120.8(4) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C15 120.0(4) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C14 C15 C10 120.2(4) . . ?
C14 C15 H15 119.9 . . ?
C10 C15 H15 119.9 . . ?
O7 C16 O8 123.9(4) . . ?
O7 C16 C12 119.2(3) . . ?
O8 C16 C12 116.9(3) . . ?
O10 C17 O9 121.1(4) . . ?
O10 C17 C18 120.2(4) . . ?
O9 C17 C18 118.7(4) . . ?
O10 C17 Gd1 60.4(2) . . ?
O9 C17 Gd1 60.8(2) . . ?
C18 C17 Gd1 178.4(3) . . ?
C19 C18 C23 119.3(4) . . ?
C19 C18 C17 120.8(4) . . ?
C23 C18 C17 119.8(4) . . ?
C18 C19 C20 120.6(4) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C21 C20 C19 119.5(4) . . ?
C21 C20 C24 121.1(4) . . ?
C19 C20 C24 119.2(4) . . ?
C22 C21 C20 119.7(4) . . ?
C22 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?
C23 C22 C21 121.1(4) . . ?
C23 C22 H22 119.4 . . ?
C21 C22 H22 119.5 . . ?
C22 C23 C18 119.7(4) . . ?
C22 C23 H23 120.1 . . ?
C18 C23 H23 120.1 . . ?
O11 C24 O12 120.1(4) . . ?
O11 C24 C20 119.4(4) . . ?
O12 C24 C20 120.3(4) . . ?
O11 C24 Gd2 59.8(2) . 1_565 ?
O12 C24 Gd2 62.1(2) . 1_565 ?
C20 C24 Gd2 161.8(3) . 1_565 ?
O14 C25 O13 122.5(4) . . ?
O14 C25 Gd2 63.5(2) . . ?
O13 C25 Gd2 58.9(2) . . ?
O14 C25 H25 118.8 . . ?
O13 C25 H25 118.8 . . ?
Gd2 C25 H25 177.7 . . ?
N1 C26 H26A 109.5 . . ?
N1 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
N1 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
N1 C27 H27A 109.5 . . ?
N1 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
N1 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C27 N1 C26 116.9(8) . . ?
C27 N1 H1A 108.1 . . ?
C26 N1 H1A 108.1 . . ?
C27 N1 H1B 108.1 . . ?
C26 N1 H1B 108.1 . . ?
H1A N1 H1B 107.3 . . ?
C1 O1 Gd1 135.7(3) . . ?
C1 O2 Gd2 119.1(3) . . ?
C8 O3 Gd1 144.4(3) . 2_556 ?
C8 O4 Gd2 140.6(2) . 2_656 ?
C9 O5 Gd1 124.2(2) . . ?
C9 O6 Gd2 128.1(3) . . ?
C16 O7 Gd1 133.8(2) . 2 ?
C16 O8 Gd2 161.3(3) . 2_655 ?
C17 O9 Gd1 92.5(3) . . ?
C17 O10 Gd1 93.8(2) . . ?
C24 O11 Gd2 94.4(3) . 1_565 ?
C24 O12 Gd1 144.0(2) . 1_565 ?
C24 O12 Gd2 91.6(2) . 1_565 ?
Gd1 O12 Gd2 115.80(12) 1_565 1_565 ?
C25 O13 Gd2 95.9(3) . . ?
C25 O14 Gd1 142.5(3) . 1_655 ?
C25 O14 Gd2 91.3(3) . . ?
Gd1 O14 Gd2 125.99(13) 1_655 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C1 C2 C3 -14.1(6) . . . . ?
O1 C1 C2 C3 164.9(4) . . . . ?
O2 C1 C2 C7 168.3(4) . . . . ?
O1 C1 C2 C7 -12.8(6) . . . . ?
C7 C2 C3 C4 1.7(6) . . . . ?
C1 C2 C3 C4 -176.0(4) . . . . ?
C2 C3 C4 C5 -0.6(6) . . . . ?
C2 C3 C4 C8 177.7(4) . . . . ?
C3 C4 C5 C6 -0.8(7) . . . . ?
C8 C4 C5 C6 -179.1(5) . . . . ?
C4 C5 C6 C7 1.1(9) . . . . ?
C5 C6 C7 C2 0.0(8) . . . . ?
C3 C2 C7 C6 -1.4(7) . . . . ?
C1 C2 C7 C6 176.3(5) . . . . ?
C5 C4 C8 O3 9.4(6) . . . . ?
C3 C4 C8 O3 -168.9(4) . . . . ?
C5 C4 C8 O4 -171.8(4) . . . . ?
C3 C4 C8 O4 9.9(6) . . . . ?
O5 C9 C10 C15 159.6(4) . . . . ?
O6 C9 C10 C15 -20.8(6) . . . . ?
O5 C9 C10 C11 -22.5(6) . . . . ?
O6 C9 C10 C11 157.1(4) . . . . ?
C15 C10 C11 C12 0.0(7) . . . . ?
C9 C10 C11 C12 -177.9(4) . . . . ?
C10 C11 C12 C13 -1.1(7) . . . . ?
C10 C11 C12 C16 176.8(4) . . . . ?
C11 C12 C13 C14 1.4(8) . . . . ?
C16 C12 C13 C14 -176.5(5) . . . . ?
C12 C13 C14 C15 -0.7(9) . . . . ?
C13 C14 C15 C10 -0.4(8) . . . . ?
C11 C10 C15 C14 0.7(7) . . . . ?
C9 C10 C15 C14 178.6(5) . . . . ?
C11 C12 C16 O7 7.2(6) . . . . ?
C13 C12 C16 O7 -175.0(4) . . . . ?
C11 C12 C16 O8 -172.0(4) . . . . ?
C13 C12 C16 O8 5.9(6) . . . . ?
O7 Gd1 C17 O10 3.0(3) 2 . . . ?
O5 Gd1 C17 O10 81.9(2) . . . . ?
O1 Gd1 C17 O10 -172.1(2) . . . . ?
O3 Gd1 C17 O10 -90.7(3) 2_556 . . . ?
O14 Gd1 C17 O10 -82.5(2) 1_455 . . . ?
O12 Gd1 C17 O10 110.5(2) 1_545 . . . ?
O9 Gd1 C17 O10 -176.8(4) . . . . ?
O7 Gd1 C17 O9 179.8(2) 2 . . . ?
O5 Gd1 C17 O9 -101.3(2) . . . . ?
O1 Gd1 C17 O9 4.7(2) . . . . ?
O3 Gd1 C17 O9 86.1(3) 2_556 . . . ?
O14 Gd1 C17 O9 94.3(2) 1_455 . . . ?
O12 Gd1 C17 O9 -72.7(3) 1_545 . . . ?
O10 Gd1 C17 O9 176.8(4) . . . . ?
O7 Gd1 C17 C18 -108(11) 2 . . . ?
O5 Gd1 C17 C18 -29(11) . . . . ?
O1 Gd1 C17 C18 77(11) . . . . ?
O3 Gd1 C17 C18 158(11) 2_556 . . . ?
O14 Gd1 C17 C18 166(11) 1_455 . . . ?
O12 Gd1 C17 C18 -1(12) 1_545 . . . ?
O10 Gd1 C17 C18 -111(12) . . . . ?
O9 Gd1 C17 C18 72(11) . . . . ?
O10 C17 C18 C19 173.1(4) . . . . ?
O9 C17 C18 C19 -5.4(6) . . . . ?
Gd1 C17 C18 C19 -77(12) . . . . ?
O10 C17 C18 C23 -9.2(6) . . . . ?
O9 C17 C18 C23 172.3(4) . . . . ?
Gd1 C17 C18 C23 101(11) . . . . ?
C23 C18 C19 C20 0.6(6) . . . . ?
C17 C18 C19 C20 178.3(3) . . . . ?
C18 C19 C20 C21 0.4(6) . . . . ?
C18 C19 C20 C24 -174.7(4) . . . . ?
C19 C20 C21 C22 -1.5(6) . . . . ?
C24 C20 C21 C22 173.5(4) . . . . ?
C20 C21 C22 C23 1.6(7) . . . . ?
C21 C22 C23 C18 -0.6(7) . . . . ?
C19 C18 C23 C22 -0.6(6) . . . . ?
C17 C18 C23 C22 -178.3(4) . . . . ?
C21 C20 C24 O11 -155.6(4) . . . . ?
C19 C20 C24 O11 19.5(5) . . . . ?
C21 C20 C24 O12 19.1(6) . . . . ?
C19 C20 C24 O12 -165.9(3) . . . . ?
C21 C20 C24 Gd2 -73.3(11) . . . 1_565 ?
C19 C20 C24 Gd2 101.7(9) . . . 1_565 ?
O8 Gd2 C25 O14 -19.8(3) 2_655 . . . ?
O4 Gd2 C25 O14 62.7(3) 2_656 . . . ?
O2 Gd2 C25 O14 146.9(3) . . . . ?
O6 Gd2 C25 O14 -101.5(3) . . . . ?
O11 Gd2 C25 O14 66.6(5) 1_545 . . . ?
O13 Gd2 C25 O14 -179.6(4) . . . . ?
O12 Gd2 C25 O14 -123.3(3) 1_545 . . . ?
C24 Gd2 C25 O14 -107.1(10) 1_545 . . . ?
O8 Gd2 C25 O13 159.8(3) 2_655 . . . ?
O4 Gd2 C25 O13 -117.7(3) 2_656 . . . ?
O2 Gd2 C25 O13 -33.5(3) . . . . ?
O6 Gd2 C25 O13 78.1(3) . . . . ?
O11 Gd2 C25 O13 -113.8(4) 1_545 . . . ?
O12 Gd2 C25 O13 56.3(3) 1_545 . . . ?
O14 Gd2 C25 O13 179.6(4) . . . . ?
C24 Gd2 C25 O13 72.5(10) 1_545 . . . ?
O2 C1 O1 Gd1 89.7(5) . . . . ?
C2 C1 O1 Gd1 -89.2(5) . . . . ?
O7 Gd1 O1 C1 7.5(6) 2 . . . ?
O5 Gd1 O1 C1 -111.2(4) . . . . ?
O3 Gd1 O1 C1 27.2(4) 2_556 . . . ?
O14 Gd1 O1 C1 101.7(4) 1_455 . . . ?
O12 Gd1 O1 C1 -49.4(4) 1_545 . . . ?
O10 Gd1 O1 C1 170.9(4) . . . . ?
O9 Gd1 O1 C1 177.2(4) . . . . ?
C17 Gd1 O1 C1 175.0(4) . . . . ?
O1 C1 O2 Gd2 -11.5(6) . . . . ?
C2 C1 O2 Gd2 167.5(3) . . . . ?
O8 Gd2 O2 C1 -115.3(4) 2_655 . . . ?
O4 Gd2 O2 C1 -178.5(4) 2_656 . . . ?
O6 Gd2 O2 C1 19.0(4) . . . . ?
O11 Gd2 O2 C1 -98.7(3) 1_545 . . . ?
O13 Gd2 O2 C1 86.4(3) . . . . ?
O12 Gd2 O2 C1 -46.6(3) 1_545 . . . ?
O14 Gd2 O2 C1 115.7(3) . . . . ?
C24 Gd2 O2 C1 -73.0(3) 1_545 . . . ?
C25 Gd2 O2 C1 100.4(3) . . . . ?
O4 C8 O3 Gd1 -19.7(8) . . . 2_556 ?
C4 C8 O3 Gd1 159.0(3) . . . 2_556 ?
O3 C8 O4 Gd2 -26.6(7) . . . 2_656 ?
C4 C8 O4 Gd2 154.7(3) . . . 2_656 ?
O6 C9 O5 Gd1 -15.4(6) . . . . ?
C10 C9 O5 Gd1 164.2(3) . . . . ?
O7 Gd1 O5 C9 -146.9(3) 2 . . . ?
O1 Gd1 O5 C9 13.4(4) . . . . ?
O3 Gd1 O5 C9 -79.2(4) 2_556 . . . ?
O14 Gd1 O5 C9 131.5(3) 1_455 . . . ?
O12 Gd1 O5 C9 -52.4(3) 1_545 . . . ?
O10 Gd1 O5 C9 133.9(4) . . . . ?
O9 Gd1 O5 C9 80.1(3) . . . . ?
C17 Gd1 O5 C9 106.8(3) . . . . ?
O5 C9 O6 Gd2 86.7(5) . . . . ?
C10 C9 O6 Gd2 -92.9(4) . . . . ?
O8 Gd2 O6 C9 53.6(3) 2_655 . . . ?
O4 Gd2 O6 C9 115.4(4) 2_656 . . . ?
O2 Gd2 O6 C9 -110.1(3) . . . . ?
O11 Gd2 O6 C9 -20.1(3) 1_545 . . . ?
O13 Gd2 O6 C9 -178.9(3) . . . . ?
O12 Gd2 O6 C9 -36.8(3) 1_545 . . . ?
O14 Gd2 O6 C9 130.8(3) . . . . ?
C24 Gd2 O6 C9 -25.2(3) 1_545 . . . ?
C25 Gd2 O6 C9 155.5(3) . . . . ?
O8 C16 O7 Gd1 -1.4(6) . . . 2 ?
C12 C16 O7 Gd1 179.5(3) . . . 2 ?
O7 C16 O8 Gd2 -22.0(11) . . . 2_655 ?
C12 C16 O8 Gd2 157.1(7) . . . 2_655 ?
O10 C17 O9 Gd1 3.2(4) . . . . ?
C18 C17 O9 Gd1 -178.3(3) . . . . ?
O7 Gd1 O9 C17 -0.2(3) 2 . . . ?
O5 Gd1 O9 C17 71.9(2) . . . . ?
O1 Gd1 O9 C17 -175.1(2) . . . . ?
O3 Gd1 O9 C17 -128.2(2) 2_556 . . . ?
O14 Gd1 O9 C17 -78.5(2) 1_455 . . . ?
O12 Gd1 O9 C17 127.5(2) 1_545 . . . ?
O10 Gd1 O9 C17 -1.7(2) . . . . ?
O9 C17 O10 Gd1 -3.2(4) . . . . ?
C18 C17 O10 Gd1 178.3(3) . . . . ?
O7 Gd1 O10 C17 -177.0(3) 2 . . . ?
O5 Gd1 O10 C17 -89.3(2) . . . . ?
O1 Gd1 O10 C17 9.4(3) . . . . ?
O3 Gd1 O10 C17 124.5(2) 2_556 . . . ?
O14 Gd1 O10 C17 89.2(2) 1_455 . . . ?
O12 Gd1 O10 C17 -98.3(3) 1_545 . . . ?
O9 Gd1 O10 C17 1.8(2) . . . . ?
O12 C24 O11 Gd2 -15.6(4) . . . 1_565 ?
C20 C24 O11 Gd2 159.1(3) . . . 1_565 ?
O11 C24 O12 Gd1 -125.9(4) . . . 1_565 ?
C20 C24 O12 Gd1 59.5(6) . . . 1_565 ?
Gd2 C24 O12 Gd1 -141.2(4) 1_565 . . 1_565 ?
O11 C24 O12 Gd2 15.3(4) . . . 1_565 ?
C20 C24 O12 Gd2 -159.4(3) . . . 1_565 ?
O14 C25 O13 Gd2 0.4(5) . . . . ?
O8 Gd2 O13 C25 -24.1(3) 2_655 . . . ?
O4 Gd2 O13 C25 61.5(3) 2_656 . . . ?
O2 Gd2 O13 C25 145.9(3) . . . . ?
O6 Gd2 O13 C25 -96.0(3) . . . . ?
O11 Gd2 O13 C25 133.5(3) 1_545 . . . ?
O12 Gd2 O13 C25 -144.4(2) 1_545 . . . ?
O14 Gd2 O13 C25 -0.2(2) . . . . ?
C24 Gd2 O13 C25 -166.0(3) 1_545 . . . ?
O13 C25 O14 Gd1 -174.8(3) . . . 1_655 ?
Gd2 C25 O14 Gd1 -174.4(5) . . . 1_655 ?
O13 C25 O14 Gd2 -0.4(5) . . . . ?
O8 Gd2 O14 C25 160.0(3) 2_655 . . . ?
O4 Gd2 O14 C25 -111.8(3) 2_656 . . . ?
O2 Gd2 O14 C25 -38.1(3) . . . . ?
O6 Gd2 O14 C25 74.9(3) . . . . ?
O11 Gd2 O14 C25 -150.0(3) 1_545 . . . ?
O13 Gd2 O14 C25 0.2(2) . . . . ?
O12 Gd2 O14 C25 100.9(3) 1_545 . . . ?
C24 Gd2 O14 C25 163.8(3) 1_545 . . . ?
O8 Gd2 O14 Gd1 -24.26(15) 2_655 . . 1_655 ?
O4 Gd2 O14 Gd1 63.94(15) 2_656 . . 1_655 ?
O2 Gd2 O14 Gd1 137.63(15) . . . 1_655 ?
O6 Gd2 O14 Gd1 -109.30(15) . . . 1_655 ?
O11 Gd2 O14 Gd1 25.7(2) 1_545 . . 1_655 ?
O13 Gd2 O14 Gd1 176.0(2) . . . 1_655 ?
O12 Gd2 O14 Gd1 -83.3(2) 1_545 . . 1_655 ?
C24 Gd2 O14 Gd1 -20.5(3) 1_545 . . 1_655 ?
C25 Gd2 O14 Gd1 175.8(4) . . . 1_655 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O13 0.90 1.98 2.832(6) 157.0 .
N1 H1A O6 0.90 2.58 3.148(7) 121.6 .
N1 H1B O9 0.90 1.84 2.722(5) 167.5 .

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.946
_refine_diff_density_min         -0.846
_refine_diff_density_rms         0.122
_database_code_depnum_ccdc_archive 'CCDC 981208'
#######################################################################
#
#                 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_3

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H13 Sm2 O14, C2 H8 N'
_chemical_formula_sum            'C27 H21 Sm2 N O14'
_chemical_formula_weight         884.17

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sm Sm -0.1638 3.4418 '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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1'
_space_group_name_Hall           '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.3911(2)
_cell_length_b                   10.5518(3)
_cell_length_c                   17.4632(5)
_cell_angle_alpha                98.993(3)
_cell_angle_beta                 97.112(2)
_cell_angle_gamma                100.424(3)
_cell_volume                     1483.48(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8909
_cell_measurement_theta_min      2.9430
_cell_measurement_theta_max      28.3370

_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.979
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             852
_exptl_crystal_F_000'            851.78
_exptl_absorpt_coefficient_mu    3.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.63995
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            13786
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_sigmaI/netI    0.0331
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.82
_diffrn_reflns_theta_max         25.00
_reflns_number_total             5226
_reflns_number_gt                4598
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP, Ver. 6.10, Bruker AXS Inc., 2000.'
_computing_publication_material  'SHELXTL-Bruker AXS Inc., 1998.'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0160P)²+0.3593P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5219
_refine_ls_number_parameters     399
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0270
_refine_ls_R_factor_gt           0.0206
_refine_ls_wR_factor_ref         0.0448
_refine_ls_wR_factor_gt          0.0428
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Sm1 Sm 0.521363(19) 0.137859(16) 0.296433(9) 0.01731(6) Uani 1 1 d . . .
Sm2 Sm 1.034631(18) 0.190852(15) 0.237465(8) 0.01522(5) Uani 1 1 d . . .
C1 C 1.0259(4) 0.4417(3) 0.19563(19) 0.0227(7) Uani 1 1 d . . .
C2 C 1.0276(4) 0.5714(3) 0.1714(2) 0.0257(8) Uani 1 1 d . . .
C3 C 1.1226(4) 0.6848(3) 0.21756(19) 0.0235(7) Uani 1 1 d . . .
H13 H 1.1840 0.6803 0.2648 0.028 Uiso 1 1 calc R . .
C4 C 1.1277(4) 0.8055(3) 0.19442(18) 0.0208(7) Uani 1 1 d . . .
C5 C 1.0347(4) 0.8113(3) 0.1243(2) 0.0316(9) Uani 1 1 d . . .
H11 H 1.0354 0.8918 0.1088 0.038 Uiso 1 1 calc R . .
C6 C 0.9403(5) 0.6978(4) 0.0769(2) 0.0403(10) Uani 1 1 d . . .
H10 H 0.8798 0.7021 0.0294 0.048 Uiso 1 1 calc R . .
C7 C 0.9366(4) 0.5786(4) 0.1008(2) 0.0347(9) Uani 1 1 d . . .
H12 H 0.8728 0.5027 0.0693 0.042 Uiso 1 1 calc R . .
C8 C 1.2413(4) 0.9227(3) 0.24236(19) 0.0220(7) Uani 1 1 d . . .
C9 C 0.8391(4) 0.0017(3) 0.35876(18) 0.0218(7) Uani 1 1 d . . .
C10 C 0.8725(4) -0.0939(3) 0.41111(17) 0.0204(7) Uani 1 1 d . . .
C11 C 0.9980(4) -0.1622(4) 0.4022(2) 0.0333(9) Uani 1 1 d . . .
H21 H 1.0618 -0.1498 0.3630 0.040 Uiso 1 1 calc R . .
C12 C 1.0278(5) -0.2482(4) 0.4512(2) 0.0453(11) Uani 1 1 d . . .
H18 H 1.1101 -0.2953 0.4440 0.054 Uiso 1 1 calc R . .
C13 C 0.9373(5) -0.2656(4) 0.5110(2) 0.0337(9) Uani 1 1 d . . .
H19 H 0.9595 -0.3231 0.5443 0.040 Uiso 1 1 calc R . .
C14 C 0.8128(4) -0.1967(3) 0.52119(18) 0.0225(7) Uani 1 1 d . . .
C15 C 0.7802(4) -0.1129(3) 0.47042(17) 0.0207(7) Uani 1 1 d . . .
H20 H 0.6949 -0.0686 0.4762 0.025 Uiso 1 1 calc R . .
C16 C 0.7187(5) -0.2090(3) 0.58747(19) 0.0280(8) Uani 1 1 d . . .
C17 C 0.6883(4) -0.0001(3) 0.13666(18) 0.0228(7) Uani 1 1 d . . .
C18 C 0.5984(4) -0.0941(3) 0.06496(18) 0.0214(7) Uani 1 1 d . . .
C19 C 0.4344(4) -0.1515(4) 0.0626(2) 0.0360(9) Uani 1 1 d . . .
H15 H 0.3837 -0.1341 0.1064 0.043 Uiso 1 1 calc R . .
C20 C 0.3469(4) -0.2336(4) -0.0039(2) 0.0425(10) Uani 1 1 d . . .
H14 H 0.2378 -0.2724 -0.0048 0.051 Uiso 1 1 calc R . .
C21 C 0.4204(4) -0.2588(4) -0.0697(2) 0.0319(9) Uani 1 1 d . . .
H16 H 0.3598 -0.3126 -0.1151 0.038 Uiso 1 1 calc R . .
C22 C 0.5836(4) -0.2045(3) -0.06822(17) 0.0199(7) Uani 1 1 d . . .
C23 C 0.6726(4) -0.1210(3) -0.00053(17) 0.0196(7) Uani 1 1 d . . .
H17 H 0.7822 -0.0832 0.0005 0.023 Uiso 1 1 calc R . .
C24 C 0.6606(4) -0.2295(3) -0.14022(18) 0.0202(7) Uani 1 1 d . . .
C25 C 0.7858(4) 0.3723(4) 0.3378(2) 0.0316(9) Uani 1 1 d . . .
H9 H 0.8669 0.4482 0.3512 0.038 Uiso 1 1 calc R . .
C26 C 1.5384(8) 0.6154(7) 0.2625(6) 0.158(4) Uani 1 1 d . . .
H3 H 1.5134 0.5684 0.2093 0.236 Uiso 1 1 calc R . .
H2 H 1.6536 0.6266 0.2809 0.236 Uiso 1 1 calc R . .
H7 H 1.5097 0.6998 0.2646 0.236 Uiso 1 1 calc R . .
C27 C 1.4395(9) 0.6129(7) 0.3928(5) 0.155(4) Uani 1 1 d . . .
H6 H 1.3878 0.6861 0.3889 0.232 Uiso 1 1 calc R . .
H5 H 1.5490 0.6435 0.4209 0.232 Uiso 1 1 calc R . .
H4 H 1.3777 0.5541 0.4203 0.232 Uiso 1 1 calc R . .
N15 N 1.4456(5) 0.5421(4) 0.3119(3) 0.0892(17) Uani 1 1 d . . .
H8 H 1.4881 0.4708 0.3168 0.107 Uiso 1 1 calc R . .
H1 H 1.3419 0.5137 0.2867 0.107 Uiso 1 1 calc R . .
O1 O 1.1248(3) 0.4349(2) 0.25617(13) 0.0282(5) Uani 1 1 d . . .
O2 O 0.9286(3) 0.3426(2) 0.15765(13) 0.0288(6) Uani 1 1 d . . .
O3 O 1.3586(3) 0.9101(2) 0.29022(14) 0.0338(6) Uani 1 1 d . . .
O4 O 1.2254(3) 1.0374(2) 0.23106(13) 0.0253(5) Uani 1 1 d . . .
O5 O 0.8376(3) 0.0455(2) 0.14082(13) 0.0273(5) Uani 1 1 d . . .
O6 O 0.6047(3) 0.0289(3) 0.18983(13) 0.0346(6) Uani 1 1 d . . .
O7 O 0.8135(3) -0.2125(2) -0.13194(13) 0.0301(6) Uani 1 1 d . . .
O8 O 0.5674(3) -0.2675(2) -0.20657(12) 0.0249(5) Uani 1 1 d . . .
O9 O 0.7100(3) 0.0457(2) 0.36471(13) 0.0314(6) Uani 1 1 d . . .
O10 O 0.9389(3) 0.0311(2) 0.31374(13) 0.0276(5) Uani 1 1 d . . .
O11 O 0.5898(3) -0.1650(3) 0.58519(14) 0.0408(7) Uani 1 1 d . . .
O12 O 0.7721(3) -0.2606(3) 0.64359(13) 0.0396(7) Uani 1 1 d . . .
O13 O 0.8169(3) 0.2739(2) 0.29827(14) 0.0316(6) Uani 1 1 d . . .
O14 O 0.6514(3) 0.3740(2) 0.36017(14) 0.0355(6) 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
Sm1 O6 2.285(2) . ?
Sm1 O9 2.308(2) . ?
Sm1 O11 2.369(2) 2_656 ?
Sm1 O8 2.375(2) 2_655 ?
Sm1 O3 2.519(2) 1_445 ?
Sm1 O14 2.547(2) . ?
Sm1 O4 2.562(2) 1_445 ?
Sm1 O13 2.625(2) . ?
Sm1 C8 2.901(3) 1_445 ?
Sm1 C25 2.936(4) . ?
Sm2 O5 2.349(2) . ?
Sm2 O7 2.383(2) 2_755 ?
Sm2 O10 2.395(2) . ?
Sm2 O12 2.396(2) 2_756 ?
Sm2 O13 2.450(2) . ?
Sm2 O4 2.474(2) 1_545 ?
Sm2 O2 2.491(2) . ?
Sm2 O1 2.506(2) . ?
Sm2 C1 2.865(3) . ?
C1 O2 1.241(4) . ?
C1 O1 1.281(4) . ?
C1 C2 1.492(5) . ?
C2 C3 1.382(5) . ?
C2 C7 1.388(5) . ?
C3 C4 1.390(4) . ?
C4 C5 1.384(5) . ?
C4 C8 1.480(5) . ?
C5 C6 1.389(5) . ?
C6 C7 1.383(5) . ?
C8 O3 1.250(4) . ?
C8 O4 1.283(4) . ?
C8 Sm1 2.901(3) 1_665 ?
C9 O10 1.249(4) . ?
C9 O9 1.263(4) . ?
C9 C10 1.502(4) . ?
C10 C15 1.386(4) . ?
C10 C11 1.391(4) . ?
C11 C12 1.375(5) . ?
C12 C13 1.381(5) . ?
C13 C14 1.390(5) . ?
C14 C15 1.384(4) . ?
C14 C16 1.488(4) . ?
C16 O11 1.251(4) . ?
C16 O12 1.266(4) . ?
C17 O5 1.247(4) . ?
C17 O6 1.264(4) . ?
C17 C18 1.493(5) . ?
C18 C23 1.384(4) . ?
C18 C19 1.393(5) . ?
C19 C20 1.372(5) . ?
C20 C21 1.382(5) . ?
C21 C22 1.381(5) . ?
C22 C23 1.396(4) . ?
C22 C24 1.492(4) . ?
C24 O7 1.250(4) . ?
C24 O8 1.277(4) . ?
C25 O14 1.241(4) . ?
C25 O13 1.242(4) . ?
C26 N15 1.451(8) . ?
C27 N15 1.503(8) . ?
O3 Sm1 2.519(2) 1_665 ?
O4 Sm2 2.474(2) 1_565 ?
O4 Sm1 2.562(2) 1_665 ?
O7 Sm2 2.383(2) 2_755 ?
O8 Sm1 2.375(2) 2_655 ?
O11 Sm1 2.369(2) 2_656 ?
O12 Sm2 2.396(2) 2_756 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O6 Sm1 O9 82.92(8) . . ?
O6 Sm1 O11 157.43(9) . 2_656 ?
O9 Sm1 O11 85.19(9) . 2_656 ?
O6 Sm1 O8 83.86(8) . 2_655 ?
O9 Sm1 O8 155.32(8) . 2_655 ?
O11 Sm1 O8 113.58(8) 2_656 2_655 ?
O6 Sm1 O3 79.95(9) . 1_445 ?
O9 Sm1 O3 78.61(8) . 1_445 ?
O11 Sm1 O3 78.94(9) 2_656 1_445 ?
O8 Sm1 O3 119.30(8) 2_655 1_445 ?
O6 Sm1 O14 123.15(9) . . ?
O9 Sm1 O14 95.52(9) . . ?
O11 Sm1 O14 77.02(9) 2_656 . ?
O8 Sm1 O14 74.63(8) 2_655 . ?
O3 Sm1 O14 155.65(8) 1_445 . ?
O6 Sm1 O4 87.67(8) . 1_445 ?
O9 Sm1 O4 129.75(8) . 1_445 ?
O11 Sm1 O4 85.28(9) 2_656 1_445 ?
O8 Sm1 O4 70.22(7) 2_655 1_445 ?
O3 Sm1 O4 51.14(7) 1_445 1_445 ?
O14 Sm1 O4 129.70(7) . 1_445 ?
O6 Sm1 O13 76.98(8) . . ?
O9 Sm1 O13 71.14(8) . . ?
O11 Sm1 O13 116.94(9) 2_656 . ?
O8 Sm1 O13 85.62(8) 2_655 . ?
O3 Sm1 O13 143.75(7) 1_445 . ?
O14 Sm1 O13 49.88(7) . . ?
O4 Sm1 O13 152.70(7) 1_445 . ?
O6 Sm1 C8 79.29(9) . 1_445 ?
O9 Sm1 C8 103.73(9) . 1_445 ?
O11 Sm1 C8 85.02(9) 2_656 1_445 ?
O8 Sm1 C8 94.13(9) 2_655 1_445 ?
O3 Sm1 C8 25.43(8) 1_445 1_445 ?
O14 Sm1 C8 152.42(8) . 1_445 ?
O4 Sm1 C8 26.24(8) 1_445 1_445 ?
O13 Sm1 C8 156.16(8) . 1_445 ?
O6 Sm1 C25 100.22(10) . . ?
O9 Sm1 C25 82.98(9) . . ?
O11 Sm1 C25 97.28(10) 2_656 . ?
O8 Sm1 C25 78.98(9) 2_655 . ?
O3 Sm1 C25 161.44(9) 1_445 . ?
O14 Sm1 C25 24.87(8) . . ?
O4 Sm1 C25 147.21(8) 1_445 . ?
O13 Sm1 C25 25.01(8) . . ?
C8 Sm1 C25 173.10(9) 1_445 . ?
O5 Sm2 O7 84.04(8) . 2_755 ?
O5 Sm2 O10 80.61(8) . . ?
O7 Sm2 O10 139.93(8) 2_755 . ?
O5 Sm2 O12 157.22(8) . 2_756 ?
O7 Sm2 O12 106.78(8) 2_755 2_756 ?
O10 Sm2 O12 78.36(8) . 2_756 ?
O5 Sm2 O13 90.39(8) . . ?
O7 Sm2 O13 141.68(8) 2_755 . ?
O10 Sm2 O13 75.40(7) . . ?
O12 Sm2 O13 92.70(9) 2_756 . ?
O5 Sm2 O4 91.54(8) . 1_545 ?
O7 Sm2 O4 69.11(7) 2_755 1_545 ?
O10 Sm2 O4 74.54(7) . 1_545 ?
O12 Sm2 O4 74.51(9) 2_756 1_545 ?
O13 Sm2 O4 149.12(7) . 1_545 ?
O5 Sm2 O2 78.00(8) . . ?
O7 Sm2 O2 70.35(8) 2_755 . ?
O10 Sm2 O2 140.02(8) . . ?
O12 Sm2 O2 124.28(8) 2_756 . ?
O13 Sm2 O2 71.41(8) . . ?
O4 Sm2 O2 138.93(7) 1_545 . ?
O5 Sm2 O1 130.07(7) . . ?
O7 Sm2 O1 78.64(8) 2_755 . ?
O10 Sm2 O1 137.84(8) . . ?
O12 Sm2 O1 72.45(8) 2_756 . ?
O13 Sm2 O1 76.29(8) . . ?
O4 Sm2 O1 123.76(7) 1_545 . ?
O2 Sm2 O1 52.09(7) . . ?
O5 Sm2 C1 103.54(9) . . ?
O7 Sm2 C1 71.75(8) 2_755 . ?
O10 Sm2 C1 147.97(8) . . ?
O12 Sm2 C1 98.93(9) 2_756 . ?
O13 Sm2 C1 72.85(8) . . ?
O4 Sm2 C1 136.07(8) 1_545 . ?
O2 Sm2 C1 25.60(8) . . ?
O1 Sm2 C1 26.52(8) . . ?
O2 C1 O1 120.9(3) . . ?
O2 C1 C2 120.0(3) . . ?
O1 C1 C2 119.1(3) . . ?
O2 C1 Sm2 60.11(16) . . ?
O1 C1 Sm2 60.91(16) . . ?
C2 C1 Sm2 177.2(2) . . ?
C3 C2 C7 119.2(3) . . ?
C3 C2 C1 120.8(3) . . ?
C7 C2 C1 119.9(3) . . ?
C2 C3 C4 121.1(3) . . ?
C5 C4 C3 119.0(3) . . ?
C5 C4 C8 121.7(3) . . ?
C3 C4 C8 119.2(3) . . ?
C4 C5 C6 120.5(3) . . ?
C7 C6 C5 119.7(3) . . ?
C6 C7 C2 120.4(3) . . ?
O3 C8 O4 119.9(3) . . ?
O3 C8 C4 120.2(3) . . ?
O4 C8 C4 119.7(3) . . ?
O3 C8 Sm1 59.93(17) . 1_665 ?
O4 C8 Sm1 61.95(17) . 1_665 ?
C4 C8 Sm1 162.1(2) . 1_665 ?
O10 C9 O9 125.6(3) . . ?
O10 C9 C10 118.5(3) . . ?
O9 C9 C10 115.9(3) . . ?
C15 C10 C11 118.9(3) . . ?
C15 C10 C9 120.1(3) . . ?
C11 C10 C9 120.9(3) . . ?
C12 C11 C10 120.1(3) . . ?
C11 C12 C13 120.9(3) . . ?
C12 C13 C14 119.6(3) . . ?
C15 C14 C13 119.3(3) . . ?
C15 C14 C16 120.0(3) . . ?
C13 C14 C16 120.6(3) . . ?
C14 C15 C10 121.1(3) . . ?
O11 C16 O12 122.9(3) . . ?
O11 C16 C14 117.3(3) . . ?
O12 C16 C14 119.7(3) . . ?
O5 C17 O6 124.1(3) . . ?
O5 C17 C18 119.5(3) . . ?
O6 C17 C18 116.4(3) . . ?
C23 C18 C19 119.2(3) . . ?
C23 C18 C17 121.3(3) . . ?
C19 C18 C17 119.4(3) . . ?
C20 C19 C18 120.5(3) . . ?
C19 C20 C21 120.2(3) . . ?
C22 C21 C20 120.3(3) . . ?
C21 C22 C23 119.5(3) . . ?
C21 C22 C24 119.8(3) . . ?
C23 C22 C24 120.6(3) . . ?
C18 C23 C22 120.2(3) . . ?
O7 C24 O8 123.7(3) . . ?
O7 C24 C22 117.8(3) . . ?
O8 C24 C22 118.6(3) . . ?
O14 C25 O13 123.0(3) . . ?
O14 C25 Sm1 59.70(18) . . ?
O13 C25 Sm1 63.33(19) . . ?
C26 N15 C27 117.0(6) . . ?
C1 O1 Sm2 92.57(19) . . ?
C1 O2 Sm2 94.29(19) . . ?
C8 O3 Sm1 94.64(19) . 1_665 ?
C8 O4 Sm2 142.9(2) . 1_565 ?
C8 O4 Sm1 91.81(19) . 1_665 ?
Sm2 O4 Sm1 114.88(9) 1_565 1_665 ?
C17 O5 Sm2 133.6(2) . . ?
C17 O6 Sm1 161.7(2) . . ?
C24 O7 Sm2 123.21(19) . 2_755 ?
C24 O8 Sm1 128.4(2) . 2_655 ?
C9 O9 Sm1 142.0(2) . . ?
C9 O10 Sm2 144.3(2) . . ?
C16 O11 Sm1 116.4(2) . 2_656 ?
C16 O12 Sm2 136.8(2) . 2_756 ?
C25 O13 Sm2 143.0(2) . . ?
C25 O13 Sm1 91.7(2) . . ?
Sm2 O13 Sm1 125.34(10) . . ?
C25 O14 Sm1 95.4(2) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.437
_refine_diff_density_min         -0.508
_refine_diff_density_rms         0.093
_database_code_depnum_ccdc_archive 'CCDC 981209'
