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

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 975869'
_audit_update_record             
;
2013-12-09 deposited with the CCDC.
2014-11-28 downloaded from the CCDC.
;



_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;

 ?

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         ?

_chemical_formula_sum            
'C12 H7 La N2 O7'

_chemical_formula_weight         430.11



loop_

_atom_type_symbol

_atom_type_description

_atom_type_scat_dispersion_real

_atom_type_scat_dispersion_imag

_atom_type_scat_source










C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
La La -0.2871 2.4523 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'



_symmetry_cell_setting           Monoclinic

_symmetry_space_group_name_H-M   Cc



loop_

_symmetry_equiv_pos_as_xyz




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



_cell_length_a                   17.724(3)

_cell_length_b                   10.6818(15)

_cell_length_c                   7.0003(10)

_cell_angle_alpha                90.00

_cell_angle_beta                 111.8390(10)

_cell_angle_gamma                90.00

_cell_volume                     1230.2(3)

_cell_formula_units_Z            4

_cell_measurement_temperature    296(2)

_cell_measurement_reflns_used    3887

_cell_measurement_theta_min      2.27

_cell_measurement_theta_max      28.27



_exptl_crystal_description       block

_exptl_crystal_colour            colourless

_exptl_crystal_size_max          0.19

_exptl_crystal_size_mid          0.18

_exptl_crystal_size_min          0.17

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    2.322

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             824

_exptl_absorpt_coefficient_mu    3.514

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.5548

_exptl_absorpt_correction_T_max  0.5864

_exptl_absorpt_process_details   sadabs



_exptl_special_details           
;

 ?

;



_diffrn_ambient_temperature      296(2)

_diffrn_radiation_wavelength     0.71073

_diffrn_radiation_type           MoK\a

_diffrn_radiation_source         'fine-focus sealed tube'

_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'CCD area detector'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean ?

_diffrn_standards_number         0

_diffrn_standards_interval_count 0

_diffrn_standards_interval_time  0

_diffrn_standards_decay_%        0

_diffrn_reflns_number            4627

_diffrn_reflns_av_R_equivalents  0.0139

_diffrn_reflns_av_sigmaI/netI    0.0243

_diffrn_reflns_limit_h_min       -21

_diffrn_reflns_limit_h_max       21

_diffrn_reflns_limit_k_min       -12

_diffrn_reflns_limit_k_max       12

_diffrn_reflns_limit_l_min       -8

_diffrn_reflns_limit_l_max       8

_diffrn_reflns_theta_min         2.27

_diffrn_reflns_theta_max         25.49

_reflns_number_total             2254

_reflns_number_gt                2180

_reflns_threshold_expression     >2sigma(I)



_computing_data_collection       'Bruker SMART'

_computing_cell_refinement       'Bruker SMART'

_computing_data_reduction        'Bruker SAINT'

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_computing_molecular_graphics    'Bruker SHELXTL'

_computing_publication_material  'Bruker SHELXTL'



_refine_special_details          
;

 Refinement of F² against ALL reflections.  The weighted R-factor wR and

 goodness of fit S are based on F², conventional R-factors R are based

 on F, with F set to zero for negative F². The threshold expression of

 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is

 not relevant to the choice of reflections for refinement.  R-factors based

 on F² are statistically about twice as large as those based on F, and R-

 factors based on ALL data will be even larger.

;



_refine_ls_structure_factor_coef Fsqd

_refine_ls_matrix_type           full

_refine_ls_weighting_scheme      calc

_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0214P)²+0.2495P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_primary     direct

_atom_sites_solution_secondary   difmap

_atom_sites_solution_hydrogens   geom

_refine_ls_hydrogen_treatment    constr

_refine_ls_extinction_method     none

_refine_ls_extinction_coef       ?

_refine_ls_abs_structure_details 
'Flack H D (1983), Acta Cryst. A39, 876-881'

_refine_ls_abs_structure_Flack   0.016(15)

_refine_ls_number_reflns         2254

_refine_ls_number_parameters     200

_refine_ls_number_restraints     2

_refine_ls_R_factor_all          0.0149

_refine_ls_R_factor_gt           0.0143

_refine_ls_wR_factor_ref         0.0392

_refine_ls_wR_factor_gt          0.0386

_refine_ls_goodness_of_fit_ref   1.022

_refine_ls_restrained_S_all      1.021

_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





























La1 La 0.24960(5) 0.253995(11) 0.25019(10) 0.01271(6) Uani 1 1 d . . .
N1 N 0.10358(13) 0.3060(2) -0.0416(3) 0.0128(5) Uani 1 1 d . . .
N2 N 0.13210(14) 0.0770(2) 0.1168(3) 0.0132(5) Uani 1 1 d . . .
O1 O 0.23980(12) 0.44794(19) 0.0508(3) 0.0252(5) Uani 1 1 d . . .
O2 O 0.16684(13) 0.61167(18) -0.1147(3) 0.0223(5) Uani 1 1 d . . .
O3 O 0.28262(12) 0.04436(19) 0.4039(3) 0.0252(5) Uani 1 1 d . . .
O4 O 0.25962(12) -0.15965(17) 0.4282(3) 0.0190(4) Uani 1 1 d . . .
O5 O -0.10796(13) 0.2139(2) -0.2055(4) 0.0218(5) Uani 1 1 d . . .
O6 O -0.06747(13) 0.0030(2) -0.2717(3) 0.0237(5) Uani 1 1 d . . .
H6 H -0.0862 0.0726 -0.2666 0.035 Uiso 1 1 calc R . .
O7 O 0.33177(16) 0.2835(2) 0.6480(4) 0.0299(5) Uani 1 1 d . . .
H1W H 0.3509 0.3556 0.6628 0.045 Uiso 1 1 d R . .
H2W H 0.3021 0.2743 0.7147 0.045 Uiso 1 1 d R . .
C1 C 0.09559(17) 0.4269(3) -0.1002(4) 0.0161(6) Uani 1 1 d . . .
C2 C 0.01993(18) 0.4804(3) -0.2036(5) 0.0207(7) Uani 1 1 d . . .
H2 H 0.0154 0.5631 -0.2482 0.025 Uiso 1 1 calc R . .
C3 C -0.04853(18) 0.4081(3) -0.2388(5) 0.0215(7) Uani 1 1 d . . .
H3 H -0.0997 0.4433 -0.3046 0.026 Uiso 1 1 calc R . .
C4 C -0.04215(19) 0.2835(3) -0.1776(5) 0.0163(6) Uani 1 1 d . . .
C5 C 0.0377(2) 0.2307(3) -0.0841(5) 0.0144(6) Uani 1 1 d . . .
C6 C 0.17362(16) 0.5008(3) -0.0500(4) 0.0168(6) Uani 1 1 d . . .
C7 C 0.05710(16) 0.0975(3) -0.0269(4) 0.0141(6) Uani 1 1 d . . .
C8 C 0.00635(17) -0.0071(3) -0.1224(5) 0.0177(6) Uani 1 1 d . . .
C9 C 0.03670(17) -0.1275(3) -0.0685(4) 0.0196(6) Uani 1 1 d . . .
H9 H 0.0054 -0.1961 -0.1333 0.024 Uiso 1 1 calc R . .
C10 C 0.11305(18) -0.1458(3) 0.0806(4) 0.0178(6) Uani 1 1 d . . .
H10 H 0.1336 -0.2260 0.1184 0.021 Uiso 1 1 calc R . .
C11 C 0.15839(17) -0.0403(3) 0.1726(4) 0.0155(6) Uani 1 1 d . . .
C12 C 0.23993(17) -0.0529(3) 0.3469(4) 0.0167(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







































La1 O5 2.451(2) 4 ?
La1 O3 2.459(2) . ?
La1 O1 2.468(2) . ?
La1 O2 2.477(2) 2_565 ?
La1 O4 2.535(2) 2_554 ?
La1 O7 2.638(3) . ?
La1 N1 2.692(2) . ?
La1 N2 2.709(2) . ?
N1 C1 1.346(4) . ?
N1 C5 1.356(4) . ?
N2 C11 1.343(4) . ?
N2 C7 1.354(4) . ?
O1 C6 1.256(3) . ?
O2 C6 1.258(3) . ?
O2 La1 2.477(2) 2_564 ?
O3 C12 1.260(3) . ?
O4 C12 1.264(3) . ?
O4 La1 2.535(2) 2 ?
O5 C4 1.335(4) . ?
O5 La1 2.451(2) 4_454 ?
O6 C8 1.341(4) . ?
O6 H6 0.8200 . ?
O7 H1W 0.8325 . ?
O7 H2W 0.8286 . ?
C1 C2 1.388(4) . ?
C1 C6 1.516(4) . ?
C2 C3 1.381(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.389(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.436(5) . ?
C5 C7 1.483(4) . ?
C7 C8 1.435(4) . ?
C8 C9 1.391(4) . ?
C9 C10 1.381(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.395(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.511(4) . ?



loop_

_geom_angle_atom_site_label_1

_geom_angle_atom_site_label_2

_geom_angle_atom_site_label_3

_geom_angle

_geom_angle_site_symmetry_1

_geom_angle_site_symmetry_3

_geom_angle_publ_flag















































































O5 La1 O3 90.33(8) 4 . ?
O5 La1 O1 78.84(7) 4 . ?
O3 La1 O1 165.29(8) . . ?
O5 La1 O2 126.81(7) 4 2_565 ?
O3 La1 O2 116.03(8) . 2_565 ?
O1 La1 O2 78.62(7) . 2_565 ?
O5 La1 O4 76.02(7) 4 2_554 ?
O3 La1 O4 86.74(7) . 2_554 ?
O1 La1 O4 81.04(7) . 2_554 ?
O2 La1 O4 144.79(8) 2_565 2_554 ?
O5 La1 O7 73.23(8) 4 . ?
O3 La1 O7 72.47(8) . . ?
O1 La1 O7 113.07(8) . . ?
O2 La1 O7 72.57(8) 2_565 . ?
O4 La1 O7 142.41(8) 2_554 . ?
O5 La1 N1 136.18(8) 4 . ?
O3 La1 N1 121.68(7) . . ?
O1 La1 N1 63.38(7) . . ?
O2 La1 N1 68.37(7) 2_565 . ?
O4 La1 N1 76.88(7) 2_554 . ?
O7 La1 N1 140.70(8) . . ?
O5 La1 N2 139.91(7) 4 . ?
O3 La1 N2 62.77(7) . . ?
O1 La1 N2 120.51(8) . . ?
O2 La1 N2 92.72(7) 2_565 . ?
O4 La1 N2 73.45(7) 2_554 . ?
O7 La1 N2 119.95(8) . . ?
N1 La1 N2 58.91(7) . . ?
C1 N1 C5 121.2(3) . . ?
C1 N1 La1 113.06(17) . . ?
C5 N1 La1 123.37(19) . . ?
C11 N2 C7 120.4(2) . . ?
C11 N2 La1 114.32(17) . . ?
C7 N2 La1 124.01(18) . . ?
C6 O1 La1 123.33(17) . . ?
C6 O2 La1 133.80(18) . 2_564 ?
C12 O3 La1 126.54(17) . . ?
C12 O4 La1 131.29(18) . 2 ?
C4 O5 La1 138.0(2) . 4_454 ?
C8 O6 H6 109.5 . . ?
La1 O7 H1W 106.4 . . ?
La1 O7 H2W 111.4 . . ?
H1W O7 H2W 110.8 . . ?
N1 C1 C2 121.7(3) . . ?
N1 C1 C6 116.4(2) . . ?
C2 C1 C6 121.9(3) . . ?
C3 C2 C1 118.5(3) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C2 C3 C4 121.0(3) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
O5 C4 C3 121.5(3) . . ?
O5 C4 C5 120.5(3) . . ?
C3 C4 C5 118.1(3) . . ?
N1 C5 C4 119.3(3) . . ?
N1 C5 C7 114.6(3) . . ?
C4 C5 C7 126.2(3) . . ?
O1 C6 O2 124.7(3) . . ?
O1 C6 C1 118.5(2) . . ?
O2 C6 C1 116.8(2) . . ?
N2 C7 C8 119.5(2) . . ?
N2 C7 C5 114.9(3) . . ?
C8 C7 C5 125.4(3) . . ?
O6 C8 C9 116.9(3) . . ?
O6 C8 C7 124.1(3) . . ?
C9 C8 C7 118.8(3) . . ?
C10 C9 C8 120.5(3) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C11 117.9(3) . . ?
C9 C10 H10 121.0 . . ?
C11 C10 H10 121.0 . . ?
N2 C11 C10 122.8(3) . . ?
N2 C11 C12 116.3(2) . . ?
C10 C11 C12 120.9(2) . . ?
O3 C12 O4 124.7(3) . . ?
O3 C12 C11 117.6(2) . . ?
O4 C12 C11 117.7(2) . . ?



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


































































































O5 La1 N1 C1 -52.1(2) 4 . . . ?
O3 La1 N1 C1 177.16(17) . . . . ?
O1 La1 N1 C1 -18.67(17) . . . . ?
O2 La1 N1 C1 69.10(18) 2_565 . . . ?
O4 La1 N1 C1 -105.11(18) 2_554 . . . ?
O7 La1 N1 C1 75.9(2) . . . . ?
N2 La1 N1 C1 176.5(2) . . . . ?
O5 La1 N1 C5 145.4(2) 4 . . . ?
O3 La1 N1 C5 14.6(3) . . . . ?
O1 La1 N1 C5 178.8(3) . . . . ?
O2 La1 N1 C5 -93.5(2) 2_565 . . . ?
O4 La1 N1 C5 92.3(2) 2_554 . . . ?
O7 La1 N1 C5 -86.7(3) . . . . ?
N2 La1 N1 C5 13.9(2) . . . . ?
O5 La1 N2 C11 39.8(2) 4 . . . ?
O3 La1 N2 C11 -13.24(17) . . . . ?
O1 La1 N2 C11 150.37(17) . . . . ?
O2 La1 N2 C11 -131.25(18) 2_565 . . . ?
O4 La1 N2 C11 81.70(18) 2_554 . . . ?
O7 La1 N2 C11 -59.8(2) . . . . ?
N1 La1 N2 C11 166.1(2) . . . . ?
O5 La1 N2 C7 -127.4(2) 4 . . . ?
O3 La1 N2 C7 179.6(2) . . . . ?
O1 La1 N2 C7 -16.8(2) . . . . ?
O2 La1 N2 C7 61.6(2) 2_565 . . . ?
O4 La1 N2 C7 -85.5(2) 2_554 . . . ?
O7 La1 N2 C7 133.0(2) . . . . ?
N1 La1 N2 C7 -1.07(19) . . . . ?
O5 La1 O1 C6 176.1(2) 4 . . . ?
O3 La1 O1 C6 132.8(3) . . . . ?
O2 La1 O1 C6 -52.4(2) 2_565 . . . ?
O4 La1 O1 C6 98.7(2) 2_554 . . . ?
O7 La1 O1 C6 -117.7(2) . . . . ?
N1 La1 O1 C6 18.9(2) . . . . ?
N2 La1 O1 C6 34.0(2) . . . . ?
O5 La1 O3 C12 -140.6(2) 4 . . . ?
O1 La1 O3 C12 -98.4(4) . . . . ?
O2 La1 O3 C12 87.3(2) 2_565 . . . ?
O4 La1 O3 C12 -64.7(2) 2_554 . . . ?
O7 La1 O3 C12 147.1(2) . . . . ?
N1 La1 O3 C12 7.7(3) . . . . ?
N2 La1 O3 C12 8.4(2) . . . . ?
C5 N1 C1 C2 1.0(4) . . . . ?
La1 N1 C1 C2 -162.0(2) . . . . ?
C5 N1 C1 C6 -178.1(3) . . . . ?
La1 N1 C1 C6 18.9(3) . . . . ?
N1 C1 C2 C3 2.7(4) . . . . ?
C6 C1 C2 C3 -178.3(3) . . . . ?
C1 C2 C3 C4 -1.8(5) . . . . ?
La1 O5 C4 C3 -23.6(5) 4_454 . . . ?
La1 O5 C4 C5 156.9(2) 4_454 . . . ?
C2 C3 C4 O5 178.0(3) . . . . ?
C2 C3 C4 C5 -2.5(5) . . . . ?
C1 N1 C5 C4 -5.4(4) . . . . ?
La1 N1 C5 C4 155.8(2) . . . . ?
C1 N1 C5 C7 174.5(2) . . . . ?
La1 N1 C5 C7 -24.3(4) . . . . ?
O5 C4 C5 N1 -174.4(3) . . . . ?
C3 C4 C5 N1 6.1(5) . . . . ?
O5 C4 C5 C7 5.7(5) . . . . ?
C3 C4 C5 C7 -173.8(3) . . . . ?
La1 O1 C6 O2 163.5(2) . . . . ?
La1 O1 C6 C1 -16.9(3) . . . . ?
La1 O2 C6 O1 35.7(4) 2_564 . . . ?
La1 O2 C6 C1 -143.8(2) 2_564 . . . ?
N1 C1 C6 O1 -3.6(4) . . . . ?
C2 C1 C6 O1 177.3(3) . . . . ?
N1 C1 C6 O2 176.0(2) . . . . ?
C2 C1 C6 O2 -3.1(4) . . . . ?
C11 N2 C7 C8 -1.2(4) . . . . ?
La1 N2 C7 C8 165.19(18) . . . . ?
C11 N2 C7 C5 -176.2(3) . . . . ?
La1 N2 C7 C5 -9.8(3) . . . . ?
N1 C5 C7 N2 21.2(4) . . . . ?
C4 C5 C7 N2 -158.9(3) . . . . ?
N1 C5 C7 C8 -153.4(3) . . . . ?
C4 C5 C7 C8 26.5(5) . . . . ?
N2 C7 C8 O6 -177.3(3) . . . . ?
C5 C7 C8 O6 -3.0(5) . . . . ?
N2 C7 C8 C9 -1.8(4) . . . . ?
C5 C7 C8 C9 172.6(3) . . . . ?
O6 C8 C9 C10 178.5(3) . . . . ?
C7 C8 C9 C10 2.7(4) . . . . ?
C8 C9 C10 C11 -0.6(4) . . . . ?
C7 N2 C11 C10 3.5(4) . . . . ?
La1 N2 C11 C10 -164.2(2) . . . . ?
C7 N2 C11 C12 -174.9(2) . . . . ?
La1 N2 C11 C12 17.4(3) . . . . ?
C9 C10 C11 N2 -2.6(4) . . . . ?
C9 C10 C11 C12 175.8(2) . . . . ?
La1 O3 C12 O4 178.9(2) . . . . ?
La1 O3 C12 C11 -2.8(4) . . . . ?
La1 O4 C12 O3 81.0(3) 2 . . . ?
La1 O4 C12 C11 -97.3(3) 2 . . . ?
N2 C11 C12 O3 -11.1(4) . . . . ?
C10 C11 C12 O3 170.4(3) . . . . ?
N2 C11 C12 O4 167.3(2) . . . . ?
C10 C11 C12 O4 -11.2(4) . . . . ?



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



O6 H6 O5 0.82 1.65 2.460(3) 167.3 .
O7 H1W O6 0.83 2.07 2.873(3) 161.8 3_556
O7 H2W O4 0.83 2.27 3.017(3) 150.7 2



_diffrn_measured_fraction_theta_max 0.999

_diffrn_reflns_theta_full        25.49

_diffrn_measured_fraction_theta_full 0.999

_refine_diff_density_max         0.270

_refine_diff_density_min         -0.683

_refine_diff_density_rms         0.078

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

data_2
_database_code_depnum_ccdc_archive 'CCDC 975870'
_audit_update_record             
;
2013-12-09 deposited with the CCDC.
2014-11-28 downloaded from the CCDC.
;



_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;

 ?

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         ?

_chemical_formula_sum            
'C12 H7 Ce N2 O7'

_chemical_formula_weight         431.32



loop_

_atom_type_symbol

_atom_type_description

_atom_type_scat_dispersion_real

_atom_type_scat_dispersion_imag

_atom_type_scat_source










C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ce Ce -0.2486 2.6331 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'



_symmetry_cell_setting           Monoclinic

_symmetry_space_group_name_H-M   Cc



loop_

_symmetry_equiv_pos_as_xyz




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



_cell_length_a                   17.604(16)

_cell_length_b                   10.624(9)

_cell_length_c                   6.996(6)

_cell_angle_alpha                90.00

_cell_angle_beta                 111.663(8)

_cell_angle_gamma                90.00

_cell_volume                     1216.1(19)

_cell_formula_units_Z            4

_cell_measurement_temperature    296(2)

_cell_measurement_reflns_used    3342

_cell_measurement_theta_min      2.49

_cell_measurement_theta_max      28.13



_exptl_crystal_description       block

_exptl_crystal_colour            yellow

_exptl_crystal_size_max          0.41

_exptl_crystal_size_mid          0.29

_exptl_crystal_size_min          0.19

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    2.356

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             828

_exptl_absorpt_coefficient_mu    3.785

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.3059

_exptl_absorpt_correction_T_max  0.5332

_exptl_absorpt_process_details   sadabs



_exptl_special_details           
;

 ?

;



_diffrn_ambient_temperature      296(2)

_diffrn_radiation_wavelength     0.71073

_diffrn_radiation_type           MoK\a

_diffrn_radiation_source         'fine-focus sealed tube'

_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'CCD area detector'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean ?

_diffrn_standards_number         0

_diffrn_standards_interval_count 0

_diffrn_standards_interval_time  0

_diffrn_standards_decay_%        0

_diffrn_reflns_number            4455

_diffrn_reflns_av_R_equivalents  0.0150

_diffrn_reflns_av_sigmaI/netI    0.0275

_diffrn_reflns_limit_h_min       -21

_diffrn_reflns_limit_h_max       21

_diffrn_reflns_limit_k_min       -12

_diffrn_reflns_limit_k_max       12

_diffrn_reflns_limit_l_min       -8

_diffrn_reflns_limit_l_max       8

_diffrn_reflns_theta_min         2.29

_diffrn_reflns_theta_max         25.48

_reflns_number_total             2229

_reflns_number_gt                2109

_reflns_threshold_expression     >2sigma(I)



_computing_data_collection       'Bruker SMART'

_computing_cell_refinement       'Bruker SMART'

_computing_data_reduction        'Bruker SAINT'

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_computing_molecular_graphics    'Bruker SHELXTL'

_computing_publication_material  'Bruker SHELXTL'



_refine_special_details          
;

 Refinement of F² against ALL reflections.  The weighted R-factor wR and

 goodness of fit S are based on F², conventional R-factors R are based

 on F, with F set to zero for negative F². The threshold expression of

 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is

 not relevant to the choice of reflections for refinement.  R-factors based

 on F² are statistically about twice as large as those based on F, and R-

 factors based on ALL data will be even larger.

;



_refine_ls_structure_factor_coef Fsqd

_refine_ls_matrix_type           full

_refine_ls_weighting_scheme      calc

_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0124P)²+1.1080P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_primary     direct

_atom_sites_solution_secondary   difmap

_atom_sites_solution_hydrogens   geom

_refine_ls_hydrogen_treatment    constr

_refine_ls_extinction_method     none

_refine_ls_extinction_coef       ?

_refine_ls_abs_structure_details 
'Flack H D (1983), Acta Cryst. A39, 876-881'

_refine_ls_abs_structure_Flack   0.057(17)

_refine_ls_number_reflns         2229

_refine_ls_number_parameters     200

_refine_ls_number_restraints     2

_refine_ls_R_factor_all          0.0160

_refine_ls_R_factor_gt           0.0149

_refine_ls_wR_factor_ref         0.0402

_refine_ls_wR_factor_gt          0.0397

_refine_ls_goodness_of_fit_ref   1.080

_refine_ls_restrained_S_all      1.079

_refine_ls_shift/su_max          0.001

_refine_ls_shift/su_mean         0.000



loop_

_atom_site_label

_atom_site_type_symbol

_atom_site_fract_x

_atom_site_fract_y

_atom_site_fract_z

_atom_site_U_iso_or_equiv

_atom_site_adp_type

_atom_site_occupancy

_atom_site_symmetry_multiplicity

_atom_site_calc_flag

_atom_site_refinement_flags

_atom_site_disorder_assembly

_atom_site_disorder_group





























Ce1 Ce 0.24953(5) 0.246585(15) 1.25109(9) 0.01293(6) Uani 1 1 d . . .
N1 N 0.10429(18) 0.1926(3) 0.9640(4) 0.0137(6) Uani 1 1 d . . .
N2 N 0.13222(18) 0.4221(3) 1.1216(4) 0.0132(6) Uani 1 1 d . . .
O1 O 0.24115(15) 0.0521(2) 1.0586(4) 0.0247(6) Uani 1 1 d . . .
O2 O 0.16883(16) -0.1129(2) 0.8902(4) 0.0218(6) Uani 1 1 d . . .
O3 O -0.10875(16) 0.2841(3) 0.7975(4) 0.0220(6) Uani 1 1 d . . .
O4 O 0.28328(16) 0.4546(2) 1.4058(4) 0.0250(6) Uani 1 1 d . . .
O5 O 0.26044(15) 0.6589(2) 1.4335(4) 0.0198(6) Uani 1 1 d . . .
O6 O -0.06787(17) 0.4965(2) 0.7333(4) 0.0229(6) Uani 1 1 d . . .
H6 H -0.0854 0.4248 0.7322 0.034 Uiso 1 1 calc R . .
O7 O 0.33223(19) 0.2178(3) 1.6469(4) 0.0302(7) Uani 1 1 d . . .
H1W H 0.3475 0.1517 1.6524 0.045 Uiso 1 1 d R . .
H2W H 0.3122 0.2413 1.7325 0.045 Uiso 1 1 d R . .
C1 C 0.0374(2) 0.2672(3) 0.9203(6) 0.0148(8) Uani 1 1 d . . .
C2 C -0.0422(2) 0.2142(4) 0.8260(6) 0.0166(8) Uani 1 1 d . . .
C3 C -0.0480(2) 0.0892(4) 0.7659(6) 0.0222(8) Uani 1 1 d . . .
H3 H -0.0993 0.0533 0.7003 0.027 Uiso 1 1 calc R . .
C4 C 0.0207(2) 0.0177(3) 0.8018(6) 0.0205(8) Uani 1 1 d . . .
H4 H 0.0166 -0.0655 0.7575 0.025 Uiso 1 1 calc R . .
C5 C 0.0963(2) 0.0717(3) 0.9052(5) 0.0151(7) Uani 1 1 d . . .
C6 C 0.1746(2) -0.0018(3) 0.9558(5) 0.0183(8) Uani 1 1 d . . .
C7 C 0.0571(2) 0.4019(3) 0.9771(5) 0.0143(7) Uani 1 1 d . . .
C8 C 0.0061(2) 0.5062(3) 0.8823(5) 0.0162(8) Uani 1 1 d . . .
C9 C 0.0361(2) 0.6275(3) 0.9362(5) 0.0192(8) Uani 1 1 d . . .
H9 H 0.0044 0.6964 0.8718 0.023 Uiso 1 1 calc R . .
C10 C 0.1127(2) 0.6458(3) 1.0852(5) 0.0185(8) Uani 1 1 d . . .
H10 H 0.1332 0.7264 1.1232 0.022 Uiso 1 1 calc R . .
C11 C 0.1583(2) 0.5402(3) 1.1769(6) 0.0163(8) Uani 1 1 d . . .
C12 C 0.2403(2) 0.5523(3) 1.3502(5) 0.0176(8) 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







































Ce1 O3 2.416(4) 4 ?
Ce1 O4 2.436(3) . ?
Ce1 O1 2.441(3) . ?
Ce1 O2 2.450(3) 2 ?
Ce1 O5 2.509(3) 2_564 ?
Ce1 O7 2.628(4) . ?
Ce1 N1 2.666(3) . ?
Ce1 N2 2.680(3) . ?
N1 C5 1.341(5) . ?
N1 C1 1.356(5) . ?
N2 C11 1.342(5) . ?
N2 C7 1.353(5) . ?
O1 C6 1.263(4) . ?
O2 C6 1.257(4) . ?
O2 Ce1 2.450(3) 2_554 ?
O3 C2 1.339(5) . ?
O3 Ce1 2.416(4) 4_454 ?
O4 C12 1.258(4) . ?
O5 C12 1.264(4) . ?
O5 Ce1 2.509(3) 2_565 ?
O6 C8 1.338(5) . ?
O6 H6 0.8200 . ?
O7 H1W 0.7482 . ?
O7 H2W 0.8377 . ?
C1 C2 1.426(5) . ?
C1 C7 1.492(5) . ?
C2 C3 1.385(5) . ?
C3 C4 1.372(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.509(5) . ?
C7 C8 1.426(5) . ?
C8 C9 1.391(5) . ?
C9 C10 1.380(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.391(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.510(5) . ?



loop_

_geom_angle_atom_site_label_1

_geom_angle_atom_site_label_2

_geom_angle_atom_site_label_3

_geom_angle

_geom_angle_site_symmetry_1

_geom_angle_site_symmetry_3

_geom_angle_publ_flag















































































O3 Ce1 O4 89.56(10) 4 . ?
O3 Ce1 O1 78.99(9) 4 . ?
O4 Ce1 O1 165.53(9) . . ?
O3 Ce1 O2 126.13(10) 4 2 ?
O4 Ce1 O2 115.56(11) . 2 ?
O1 Ce1 O2 78.62(10) . 2 ?
O3 Ce1 O5 76.13(9) 4 2_564 ?
O4 Ce1 O5 86.83(10) . 2_564 ?
O1 Ce1 O5 81.89(11) . 2_564 ?
O2 Ce1 O5 145.97(10) 2 2_564 ?
O3 Ce1 O7 72.52(10) 4 . ?
O4 Ce1 O7 71.81(10) . . ?
O1 Ce1 O7 112.34(10) . . ?
O2 Ce1 O7 72.00(11) 2 . ?
O5 Ce1 O7 141.80(10) 2_564 . ?
O3 Ce1 N1 136.69(11) 4 . ?
O4 Ce1 N1 122.59(9) . . ?
O1 Ce1 N1 63.67(9) . . ?
O2 Ce1 N1 68.86(11) 2 . ?
O5 Ce1 N1 77.55(10) 2_564 . ?
O7 Ce1 N1 140.64(10) . . ?
O3 Ce1 N2 140.18(9) 4 . ?
O4 Ce1 N2 63.25(10) . . ?
O1 Ce1 N2 121.37(10) . . ?
O2 Ce1 N2 92.88(11) 2 . ?
O5 Ce1 N2 73.96(9) 2_564 . ?
O7 Ce1 N2 119.67(9) . . ?
N1 Ce1 N2 59.34(10) . . ?
C5 N1 C1 120.4(3) . . ?
C5 N1 Ce1 113.6(2) . . ?
C1 N1 Ce1 123.7(2) . . ?
C11 N2 C7 120.0(3) . . ?
C11 N2 Ce1 114.5(2) . . ?
C7 N2 Ce1 124.1(2) . . ?
C6 O1 Ce1 123.5(2) . . ?
C6 O2 Ce1 135.1(2) . 2_554 ?
C2 O3 Ce1 138.5(2) . 4_454 ?
C12 O4 Ce1 126.2(2) . . ?
C12 O5 Ce1 131.8(2) . 2_565 ?
C8 O6 H6 109.5 . . ?
Ce1 O7 H1W 102.2 . . ?
Ce1 O7 H2W 120.2 . . ?
H1W O7 H2W 118.7 . . ?
N1 C1 C2 119.8(3) . . ?
N1 C1 C7 113.8(3) . . ?
C2 C1 C7 126.4(3) . . ?
O3 C2 C3 121.6(4) . . ?
O3 C2 C1 120.5(3) . . ?
C3 C2 C1 118.0(3) . . ?
C4 C3 C2 120.9(4) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 118.6(3) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
N1 C5 C4 122.0(3) . . ?
N1 C5 C6 116.1(3) . . ?
C4 C5 C6 121.8(3) . . ?
O2 C6 O1 124.5(3) . . ?
O2 C6 C5 117.1(3) . . ?
O1 C6 C5 118.3(3) . . ?
N2 C7 C8 119.9(3) . . ?
N2 C7 C1 114.7(3) . . ?
C8 C7 C1 125.3(3) . . ?
O6 C8 C9 116.5(3) . . ?
O6 C8 C7 124.5(3) . . ?
C9 C8 C7 118.9(3) . . ?
C10 C9 C8 120.1(3) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C11 118.1(3) . . ?
C9 C10 H10 120.9 . . ?
C11 C10 H10 120.9 . . ?
N2 C11 C10 122.9(3) . . ?
N2 C11 C12 115.8(3) . . ?
C10 C11 C12 121.3(3) . . ?
O4 C12 O5 124.3(3) . . ?
O4 C12 C11 117.8(3) . . ?
O5 C12 C11 118.0(3) . . ?



loop_

_geom_torsion_atom_site_label_1

_geom_torsion_atom_site_label_2

_geom_torsion_atom_site_label_3

_geom_torsion_atom_site_label_4

_geom_torsion

_geom_torsion_site_symmetry_1

_geom_torsion_site_symmetry_2

_geom_torsion_site_symmetry_3

_geom_torsion_site_symmetry_4

_geom_torsion_publ_flag


































































































O3 Ce1 N1 C5 51.3(3) 4 . . . ?
O4 Ce1 N1 C5 -177.0(2) . . . . ?
O1 Ce1 N1 C5 18.0(2) . . . . ?
O2 Ce1 N1 C5 -69.4(2) 2 . . . ?
O5 Ce1 N1 C5 105.0(2) 2_564 . . . ?
O7 Ce1 N1 C5 -75.7(3) . . . . ?
N2 Ce1 N1 C5 -176.4(3) . . . . ?
O3 Ce1 N1 C1 -145.8(3) 4 . . . ?
O4 Ce1 N1 C1 -14.2(3) . . . . ?
O1 Ce1 N1 C1 -179.2(3) . . . . ?
O2 Ce1 N1 C1 93.4(3) 2 . . . ?
O5 Ce1 N1 C1 -92.1(3) 2_564 . . . ?
O7 Ce1 N1 C1 87.1(3) . . . . ?
N2 Ce1 N1 C1 -13.6(3) . . . . ?
O3 Ce1 N2 C11 -38.4(3) 4 . . . ?
O4 Ce1 N2 C11 13.4(2) . . . . ?
O1 Ce1 N2 C11 -150.9(2) . . . . ?
O2 Ce1 N2 C11 130.7(2) 2 . . . ?
O5 Ce1 N2 C11 -81.2(2) 2_564 . . . ?
O7 Ce1 N2 C11 59.8(3) . . . . ?
N1 Ce1 N2 C11 -166.0(3) . . . . ?
O3 Ce1 N2 C7 127.7(3) 4 . . . ?
O4 Ce1 N2 C7 179.6(3) . . . . ?
O1 Ce1 N2 C7 15.3(3) . . . . ?
O2 Ce1 N2 C7 -63.1(3) 2 . . . ?
O5 Ce1 N2 C7 85.0(3) 2_564 . . . ?
O7 Ce1 N2 C7 -134.0(3) . . . . ?
N1 Ce1 N2 C7 0.1(2) . . . . ?
O3 Ce1 O1 C6 -175.2(3) 4 . . . ?
O4 Ce1 O1 C6 -137.0(4) . . . . ?
O2 Ce1 O1 C6 54.1(3) 2 . . . ?
O5 Ce1 O1 C6 -97.9(3) 2_564 . . . ?
O7 Ce1 O1 C6 119.0(3) . . . . ?
N1 Ce1 O1 C6 -17.8(3) . . . . ?
N2 Ce1 O1 C6 -32.3(3) . . . . ?
O3 Ce1 O4 C12 141.4(3) 4 . . . ?
O1 Ce1 O4 C12 104.0(5) . . . . ?
O2 Ce1 O4 C12 -88.0(3) 2 . . . ?
O5 Ce1 O4 C12 65.3(3) 2_564 . . . ?
O7 Ce1 O4 C12 -146.9(3) . . . . ?
N1 Ce1 O4 C12 -7.8(3) . . . . ?
N2 Ce1 O4 C12 -8.3(3) . . . . ?
C5 N1 C1 C2 5.0(5) . . . . ?
Ce1 N1 C1 C2 -156.7(3) . . . . ?
C5 N1 C1 C7 -174.2(3) . . . . ?
Ce1 N1 C1 C7 24.1(4) . . . . ?
Ce1 O3 C2 C3 22.9(6) 4_454 . . . ?
Ce1 O3 C2 C1 -156.9(3) 4_454 . . . ?
N1 C1 C2 O3 174.4(3) . . . . ?
C7 C1 C2 O3 -6.5(6) . . . . ?
N1 C1 C2 C3 -5.5(5) . . . . ?
C7 C1 C2 C3 173.6(4) . . . . ?
O3 C2 C3 C4 -177.9(4) . . . . ?
C1 C2 C3 C4 1.9(6) . . . . ?
C2 C3 C4 C5 2.0(6) . . . . ?
C1 N1 C5 C4 -0.9(5) . . . . ?
Ce1 N1 C5 C4 162.5(3) . . . . ?
C1 N1 C5 C6 178.2(3) . . . . ?
Ce1 N1 C5 C6 -18.3(4) . . . . ?
C3 C4 C5 N1 -2.6(6) . . . . ?
C3 C4 C5 C6 178.3(4) . . . . ?
Ce1 O2 C6 O1 -36.9(5) 2_554 . . . ?
Ce1 O2 C6 C5 142.4(3) 2_554 . . . ?
Ce1 O1 C6 O2 -165.1(3) . . . . ?
Ce1 O1 C6 C5 15.6(4) . . . . ?
N1 C5 C6 O2 -175.4(3) . . . . ?
C4 C5 C6 O2 3.7(5) . . . . ?
N1 C5 C6 O1 4.0(5) . . . . ?
C4 C5 C6 O1 -176.9(3) . . . . ?
C11 N2 C7 C8 0.7(5) . . . . ?
Ce1 N2 C7 C8 -164.7(2) . . . . ?
C11 N2 C7 C1 176.4(3) . . . . ?
Ce1 N2 C7 C1 11.0(4) . . . . ?
N1 C1 C7 N2 -21.7(5) . . . . ?
C2 C1 C7 N2 159.1(4) . . . . ?
N1 C1 C7 C8 153.7(3) . . . . ?
C2 C1 C7 C8 -25.4(6) . . . . ?
N2 C7 C8 O6 177.6(3) . . . . ?
C1 C7 C8 O6 2.4(6) . . . . ?
N2 C7 C8 C9 2.0(5) . . . . ?
C1 C7 C8 C9 -173.2(4) . . . . ?
O6 C8 C9 C10 -178.5(3) . . . . ?
C7 C8 C9 C10 -2.6(5) . . . . ?
C8 C9 C10 C11 0.4(5) . . . . ?
C7 N2 C11 C10 -3.0(5) . . . . ?
Ce1 N2 C11 C10 163.8(3) . . . . ?
C7 N2 C11 C12 175.6(3) . . . . ?
Ce1 N2 C11 C12 -17.6(4) . . . . ?
C9 C10 C11 N2 2.4(5) . . . . ?
C9 C10 C11 C12 -176.1(3) . . . . ?
Ce1 O4 C12 O5 -179.3(3) . . . . ?
Ce1 O4 C12 C11 2.6(5) . . . . ?
Ce1 O5 C12 O4 -82.1(5) 2_565 . . . ?
Ce1 O5 C12 C11 96.0(4) 2_565 . . . ?
N2 C11 C12 O4 11.3(5) . . . . ?
C10 C11 C12 O4 -170.0(4) . . . . ?
N2 C11 C12 O5 -166.9(3) . . . . ?
C10 C11 C12 O5 11.7(5) . . . . ?



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



O6 H6 O3 0.82 1.66 2.459(4) 164.7 .
O7 H1W O6 0.75 2.15 2.865(4) 159.0 3_546
O7 H2W O5 0.84 2.21 3.034(4) 168.5 2_565



_diffrn_measured_fraction_theta_max 1.000

_diffrn_reflns_theta_full        25.48

_diffrn_measured_fraction_theta_full 1.000

_refine_diff_density_max         0.322

_refine_diff_density_min         -0.520

_refine_diff_density_rms         0.089

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

data_3
_database_code_depnum_ccdc_archive 'CCDC 975871'
_audit_update_record             
;
2013-12-09 deposited with the CCDC.
2014-11-28 downloaded from the CCDC.
;



_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;

 ?

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         ?

_chemical_formula_sum            
'C12 H7 N2 O7 Pr'

_chemical_formula_weight         432.11



loop_

_atom_type_symbol

_atom_type_description

_atom_type_scat_dispersion_real

_atom_type_scat_dispersion_imag

_atom_type_scat_source










C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pr Pr -0.2180 2.8214 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'



_symmetry_cell_setting           Monoclinic

_symmetry_space_group_name_H-M   Cc



loop_

_symmetry_equiv_pos_as_xyz




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



_cell_length_a                   17.570(3)

_cell_length_b                   10.6061(15)

_cell_length_c                   6.9846(10)

_cell_angle_alpha                90.00

_cell_angle_beta                 111.5980(10)

_cell_angle_gamma                90.00

_cell_volume                     1210.2(3)

_cell_formula_units_Z            4

_cell_measurement_temperature    296(2)

_cell_measurement_reflns_used    3662

_cell_measurement_theta_min      3.49

_cell_measurement_theta_max      28.21



_exptl_crystal_description       block

_exptl_crystal_colour            yellow

_exptl_crystal_size_max          0.41

_exptl_crystal_size_mid          0.29

_exptl_crystal_size_min          0.19

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    2.372

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             832

_exptl_absorpt_coefficient_mu    4.069

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.2863

_exptl_absorpt_correction_T_max  0.5120

_exptl_absorpt_process_details   sadabs



_exptl_special_details           
;

 ?

;



_diffrn_ambient_temperature      296(2)

_diffrn_radiation_wavelength     0.71073

_diffrn_radiation_type           MoK\a

_diffrn_radiation_source         'fine-focus sealed tube'

_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'CCD area detector'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean ?

_diffrn_standards_number         0

_diffrn_standards_interval_count 0

_diffrn_standards_interval_time  0

_diffrn_standards_decay_%        0

_diffrn_reflns_number            4500

_diffrn_reflns_av_R_equivalents  0.0116

_diffrn_reflns_av_sigmaI/netI    0.0165

_diffrn_reflns_limit_h_min       -21

_diffrn_reflns_limit_h_max       21

_diffrn_reflns_limit_k_min       -12

_diffrn_reflns_limit_k_max       12

_diffrn_reflns_limit_l_min       -8

_diffrn_reflns_limit_l_max       8

_diffrn_reflns_theta_min         2.29

_diffrn_reflns_theta_max         25.50

_reflns_number_total             2208

_reflns_number_gt                2135

_reflns_threshold_expression     >2sigma(I)



_computing_data_collection       'Bruker SMART'

_computing_cell_refinement       'Bruker SMART'

_computing_data_reduction        'Bruker SAINT'

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_computing_molecular_graphics    'Bruker SHELXTL'

_computing_publication_material  'Bruker SHELXTL'



_refine_special_details          
;

 Refinement of F² against ALL reflections.  The weighted R-factor wR and

 goodness of fit S are based on F², conventional R-factors R are based

 on F, with F set to zero for negative F². The threshold expression of

 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is

 not relevant to the choice of reflections for refinement.  R-factors based

 on F² are statistically about twice as large as those based on F, and R-

 factors based on ALL data will be even larger.

;



_refine_ls_structure_factor_coef Fsqd

_refine_ls_matrix_type           full

_refine_ls_weighting_scheme      calc

_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0200P)²+1.6051P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_primary     direct

_atom_sites_solution_secondary   difmap

_atom_sites_solution_hydrogens   geom

_refine_ls_hydrogen_treatment    constr

_refine_ls_extinction_method     none

_refine_ls_extinction_coef       ?

_refine_ls_abs_structure_details 
'Flack H D (1983), Acta Cryst. A39, 876-881'

_refine_ls_abs_structure_Flack   -0.044(16)

_refine_ls_number_reflns         2208

_refine_ls_number_parameters     200

_refine_ls_number_restraints     2

_refine_ls_R_factor_all          0.0153

_refine_ls_R_factor_gt           0.0148

_refine_ls_wR_factor_ref         0.0382

_refine_ls_wR_factor_gt          0.0379

_refine_ls_goodness_of_fit_ref   1.086

_refine_ls_restrained_S_all      1.086

_refine_ls_shift/su_max          0.006

_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





























Pr1 Pr 0.24921(5) 0.247219(13) 0.25002(10) 0.01164(6) Uani 1 1 d . . .
N1 N 0.10471(16) 0.1924(2) -0.0338(4) 0.0127(5) Uani 1 1 d . . .
N2 N 0.13229(16) 0.4223(2) 0.1227(4) 0.0129(5) Uani 1 1 d . . .
O1 O 0.24216(13) 0.0526(2) 0.0615(4) 0.0235(6) Uani 1 1 d . . .
O2 O 0.17025(14) -0.1130(2) -0.1091(4) 0.0206(5) Uani 1 1 d . . .
O3 O -0.10938(14) 0.2839(2) -0.2030(4) 0.0204(5) Uani 1 1 d . . .
O4 O 0.28359(15) 0.4538(2) 0.4056(4) 0.0228(5) Uani 1 1 d . . .
O5 O 0.26071(14) 0.6588(2) 0.4353(3) 0.0184(5) Uani 1 1 d . . .
O6 O -0.06839(15) 0.4968(2) -0.2664(4) 0.0224(5) Uani 1 1 d . . .
H6 H -0.0869 0.4263 -0.2624 0.034 Uiso 1 1 calc R . .
O7 O 0.33196(18) 0.2190(3) 0.6429(4) 0.0277(6) Uani 1 1 d . . .
H1W H 0.3472 0.1529 0.6484 0.042 Uiso 1 1 d R . .
H2W H 0.3119 0.2424 0.7285 0.042 Uiso 1 1 d R . .
C1 C 0.0374(2) 0.2667(3) -0.0785(5) 0.0139(7) Uani 1 1 d . . .
C2 C -0.0427(2) 0.2141(3) -0.1743(5) 0.0154(6) Uani 1 1 d . . .
C3 C -0.0481(2) 0.0887(3) -0.2336(5) 0.0200(7) Uani 1 1 d . . .
H3 H -0.0995 0.0526 -0.2990 0.024 Uiso 1 1 calc R . .
C4 C 0.0208(2) 0.0163(3) -0.1977(5) 0.0192(7) Uani 1 1 d . . .
H4 H 0.0167 -0.0670 -0.2420 0.023 Uiso 1 1 calc R . .
C5 C 0.09672(19) 0.0713(3) -0.0933(5) 0.0146(6) Uani 1 1 d . . .
C6 C 0.17607(19) -0.0016(3) -0.0422(5) 0.0166(7) Uani 1 1 d . . .
C7 C 0.05681(18) 0.4016(3) -0.0216(5) 0.0128(6) Uani 1 1 d . . .
C8 C 0.00588(19) 0.5070(3) -0.1175(5) 0.0161(7) Uani 1 1 d . . .
C9 C 0.0363(2) 0.6286(3) -0.0622(5) 0.0179(7) Uani 1 1 d . . .
H9 H 0.0046 0.6979 -0.1261 0.021 Uiso 1 1 calc R . .
C10 C 0.1130(2) 0.6469(3) 0.0865(5) 0.0169(7) Uani 1 1 d . . .
H10 H 0.1337 0.7277 0.1243 0.020 Uiso 1 1 calc R . .
C11 C 0.1588(2) 0.5405(3) 0.1788(5) 0.0146(6) Uani 1 1 d . . .
C12 C 0.2408(2) 0.5523(3) 0.3521(5) 0.0159(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







































Pr1 O3 2.406(2) 4 ?
Pr1 O4 2.422(2) . ?
Pr1 O1 2.427(2) . ?
Pr1 O2 2.434(2) 2 ?
Pr1 O5 2.488(2) 2_564 ?
Pr1 O7 2.607(3) . ?
Pr1 N1 2.647(3) . ?
Pr1 N2 2.667(3) . ?
N1 C5 1.342(4) . ?
N1 C1 1.359(4) . ?
N2 C11 1.344(4) . ?
N2 C7 1.356(4) . ?
O1 C6 1.258(4) . ?
O2 C6 1.261(4) . ?
O2 Pr1 2.434(2) 2_554 ?
O3 C2 1.337(4) . ?
O3 Pr1 2.406(2) 4_454 ?
O4 C12 1.261(4) . ?
O5 C12 1.259(4) . ?
O5 Pr1 2.488(2) 2_565 ?
O6 C8 1.340(4) . ?
O6 H6 0.8200 . ?
O7 H1W 0.7469 . ?
O7 H2W 0.8360 . ?
C1 C2 1.430(5) . ?
C1 C7 1.491(4) . ?
C2 C3 1.386(5) . ?
C3 C4 1.377(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.391(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.517(4) . ?
C7 C8 1.435(4) . ?
C8 C9 1.395(5) . ?
C9 C10 1.380(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.398(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.508(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















































































O3 Pr1 O4 89.34(9) 4 . ?
O3 Pr1 O1 78.53(8) 4 . ?
O4 Pr1 O1 165.38(8) . . ?
O3 Pr1 O2 125.32(8) 4 2 ?
O4 Pr1 O2 115.64(9) . 2 ?
O1 Pr1 O2 78.42(8) . 2 ?
O3 Pr1 O5 76.12(8) 4 2_564 ?
O4 Pr1 O5 86.91(8) . 2_564 ?
O1 Pr1 O5 82.30(8) . 2_564 ?
O2 Pr1 O5 146.62(9) 2 2_564 ?
O3 Pr1 O7 72.11(9) 4 . ?
O4 Pr1 O7 71.41(9) . . ?
O1 Pr1 O7 111.76(9) . . ?
O2 Pr1 O7 71.77(9) 2 . ?
O5 Pr1 O7 141.32(9) 2_564 . ?
O3 Pr1 N1 136.85(9) 4 . ?
O4 Pr1 N1 123.14(8) . . ?
O1 Pr1 N1 64.13(8) . . ?
O2 Pr1 N1 69.04(8) 2 . ?
O5 Pr1 N1 78.09(8) 2_564 . ?
O7 Pr1 N1 140.59(9) . . ?
O3 Pr1 N2 140.45(8) 4 . ?
O4 Pr1 N2 63.51(8) . . ?
O1 Pr1 N2 122.14(9) . . ?
O2 Pr1 N2 93.33(8) 2 . ?
O5 Pr1 N2 74.32(8) 2_564 . ?
O7 Pr1 N2 119.57(9) . . ?
N1 Pr1 N2 59.63(8) . . ?
C5 N1 C1 120.1(3) . . ?
C5 N1 Pr1 113.8(2) . . ?
C1 N1 Pr1 124.0(2) . . ?
C11 N2 C7 120.4(3) . . ?
C11 N2 Pr1 114.2(2) . . ?
C7 N2 Pr1 123.9(2) . . ?
C6 O1 Pr1 123.54(19) . . ?
C6 O2 Pr1 135.8(2) . 2_554 ?
C2 O3 Pr1 138.4(2) . 4_454 ?
C12 O4 Pr1 126.4(2) . . ?
C12 O5 Pr1 131.9(2) . 2_565 ?
C8 O6 H6 109.5 . . ?
Pr1 O7 H1W 102.3 . . ?
Pr1 O7 H2W 120.0 . . ?
H1W O7 H2W 118.7 . . ?
N1 C1 C2 120.3(3) . . ?
N1 C1 C7 113.6(3) . . ?
C2 C1 C7 126.1(3) . . ?
O3 C2 C3 121.8(3) . . ?
O3 C2 C1 120.7(3) . . ?
C3 C2 C1 117.5(3) . . ?
C4 C3 C2 121.4(3) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C5 118.1(3) . . ?
C3 C4 H4 120.9 . . ?
C5 C4 H4 120.9 . . ?
N1 C5 C4 122.3(3) . . ?
N1 C5 C6 115.7(3) . . ?
C4 C5 C6 122.0(3) . . ?
O1 C6 O2 124.9(3) . . ?
O1 C6 C5 118.4(3) . . ?
O2 C6 C5 116.6(3) . . ?
N2 C7 C8 119.5(3) . . ?
N2 C7 C1 114.8(3) . . ?
C8 C7 C1 125.5(3) . . ?
O6 C8 C9 117.0(3) . . ?
O6 C8 C7 124.1(3) . . ?
C9 C8 C7 118.8(3) . . ?
C10 C9 C8 120.5(3) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C11 118.0(3) . . ?
C9 C10 H10 121.0 . . ?
C11 C10 H10 121.0 . . ?
N2 C11 C10 122.7(3) . . ?
N2 C11 C12 116.0(3) . . ?
C10 C11 C12 121.3(3) . . ?
O4 C12 O5 124.9(3) . . ?
O4 C12 C11 117.3(3) . . ?
O5 C12 C11 117.8(3) . . ?



loop_

_geom_torsion_atom_site_label_1

_geom_torsion_atom_site_label_2

_geom_torsion_atom_site_label_3

_geom_torsion_atom_site_label_4

_geom_torsion

_geom_torsion_site_symmetry_1

_geom_torsion_site_symmetry_2

_geom_torsion_site_symmetry_3

_geom_torsion_site_symmetry_4

_geom_torsion_publ_flag


































































































O3 Pr1 N1 C5 50.4(3) 4 . . . ?
O4 Pr1 N1 C5 -177.0(2) . . . . ?
O1 Pr1 N1 C5 17.6(2) . . . . ?
O2 Pr1 N1 C5 -69.4(2) 2 . . . ?
O5 Pr1 N1 C5 104.7(2) 2_564 . . . ?
O7 Pr1 N1 C5 -75.8(3) . . . . ?
N2 Pr1 N1 C5 -176.6(2) . . . . ?
O3 Pr1 N1 C1 -146.2(2) 4 . . . ?
O4 Pr1 N1 C1 -13.7(3) . . . . ?
O1 Pr1 N1 C1 -179.1(3) . . . . ?
O2 Pr1 N1 C1 94.0(3) 2 . . . ?
O5 Pr1 N1 C1 -91.9(3) 2_564 . . . ?
O7 Pr1 N1 C1 87.5(3) . . . . ?
N2 Pr1 N1 C1 -13.3(2) . . . . ?
O3 Pr1 N2 C11 -38.0(3) 4 . . . ?
O4 Pr1 N2 C11 13.4(2) . . . . ?
O1 Pr1 N2 C11 -151.1(2) . . . . ?
O2 Pr1 N2 C11 130.5(2) 2 . . . ?
O5 Pr1 N2 C11 -81.0(2) 2_564 . . . ?
O7 Pr1 N2 C11 59.6(2) . . . . ?
N1 Pr1 N2 C11 -166.2(2) . . . . ?
O3 Pr1 N2 C7 128.3(2) 4 . . . ?
O4 Pr1 N2 C7 179.7(3) . . . . ?
O1 Pr1 N2 C7 15.2(3) . . . . ?
O2 Pr1 N2 C7 -63.2(2) 2 . . . ?
O5 Pr1 N2 C7 85.3(2) 2_564 . . . ?
O7 Pr1 N2 C7 -134.1(2) . . . . ?
N1 Pr1 N2 C7 0.1(2) . . . . ?
O3 Pr1 O1 C6 -174.7(3) 4 . . . ?
O4 Pr1 O1 C6 -140.2(3) . . . . ?
O2 Pr1 O1 C6 55.2(2) 2 . . . ?
O5 Pr1 O1 C6 -97.4(3) 2_564 . . . ?
O7 Pr1 O1 C6 120.0(3) . . . . ?
N1 Pr1 O1 C6 -16.9(2) . . . . ?
N2 Pr1 O1 C6 -31.4(3) . . . . ?
O3 Pr1 O4 C12 142.0(3) 4 . . . ?
O1 Pr1 O4 C12 108.2(4) . . . . ?
O2 Pr1 O4 C12 -88.6(3) 2 . . . ?
O5 Pr1 O4 C12 65.8(3) 2_564 . . . ?
O7 Pr1 O4 C12 -146.7(3) . . . . ?
N1 Pr1 O4 C12 -7.8(3) . . . . ?
N2 Pr1 O4 C12 -8.2(2) . . . . ?
C5 N1 C1 C2 4.9(5) . . . . ?
Pr1 N1 C1 C2 -157.4(2) . . . . ?
C5 N1 C1 C7 -174.0(3) . . . . ?
Pr1 N1 C1 C7 23.6(4) . . . . ?
Pr1 O3 C2 C3 22.6(5) 4_454 . . . ?
Pr1 O3 C2 C1 -156.7(3) 4_454 . . . ?
N1 C1 C2 O3 174.3(3) . . . . ?
C7 C1 C2 O3 -6.8(5) . . . . ?
N1 C1 C2 C3 -5.0(5) . . . . ?
C7 C1 C2 C3 173.8(3) . . . . ?
O3 C2 C3 C4 -177.9(3) . . . . ?
C1 C2 C3 C4 1.4(5) . . . . ?
C2 C3 C4 C5 2.2(5) . . . . ?
C1 N1 C5 C4 -1.2(5) . . . . ?
Pr1 N1 C5 C4 162.9(2) . . . . ?
C1 N1 C5 C6 177.9(3) . . . . ?
Pr1 N1 C5 C6 -18.1(3) . . . . ?
C3 C4 C5 N1 -2.4(5) . . . . ?
C3 C4 C5 C6 178.6(3) . . . . ?
Pr1 O1 C6 O2 -165.9(2) . . . . ?
Pr1 O1 C6 C5 14.5(4) . . . . ?
Pr1 O2 C6 O1 -37.4(5) 2_554 . . . ?
Pr1 O2 C6 C5 142.3(2) 2_554 . . . ?
N1 C5 C6 O1 4.4(4) . . . . ?
C4 C5 C6 O1 -176.6(3) . . . . ?
N1 C5 C6 O2 -175.3(3) . . . . ?
C4 C5 C6 O2 3.8(5) . . . . ?
C11 N2 C7 C8 1.3(4) . . . . ?
Pr1 N2 C7 C8 -164.2(2) . . . . ?
C11 N2 C7 C1 176.3(3) . . . . ?
Pr1 N2 C7 C1 10.9(4) . . . . ?
N1 C1 C7 N2 -21.3(4) . . . . ?
C2 C1 C7 N2 159.8(3) . . . . ?
N1 C1 C7 C8 153.5(3) . . . . ?
C2 C1 C7 C8 -25.5(5) . . . . ?
N2 C7 C8 O6 177.7(3) . . . . ?
C1 C7 C8 O6 3.2(5) . . . . ?
N2 C7 C8 C9 1.3(4) . . . . ?
C1 C7 C8 C9 -173.2(3) . . . . ?
O6 C8 C9 C10 -178.5(3) . . . . ?
C7 C8 C9 C10 -2.0(5) . . . . ?
C8 C9 C10 C11 0.1(5) . . . . ?
C7 N2 C11 C10 -3.3(5) . . . . ?
Pr1 N2 C11 C10 163.5(2) . . . . ?
C7 N2 C11 C12 175.4(3) . . . . ?
Pr1 N2 C11 C12 -17.8(3) . . . . ?
C9 C10 C11 N2 2.6(5) . . . . ?
C9 C10 C11 C12 -176.0(3) . . . . ?
Pr1 O4 C12 O5 -179.5(2) . . . . ?
Pr1 O4 C12 C11 2.2(4) . . . . ?
Pr1 O5 C12 O4 -82.5(4) 2_565 . . . ?
Pr1 O5 C12 C11 95.8(3) 2_565 . . . ?
N2 C11 C12 O4 11.8(4) . . . . ?
C10 C11 C12 O4 -169.5(3) . . . . ?
N2 C11 C12 O5 -166.7(3) . . . . ?
C10 C11 C12 O5 12.0(4) . . . . ?



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



O6 H6 O3 0.82 1.65 2.459(4) 167.5 .
O7 H1W O6 0.75 2.15 2.864(4) 158.9 3_546
O7 H2W O5 0.84 2.22 3.050(4) 169.1 2_565



_diffrn_measured_fraction_theta_max 0.999

_diffrn_reflns_theta_full        25.50

_diffrn_measured_fraction_theta_full 0.999

_refine_diff_density_max         0.378

_refine_diff_density_min         -0.462

_refine_diff_density_rms         0.064

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

data_4
_database_code_depnum_ccdc_archive 'CCDC 975872'
_audit_update_record             
;
2013-12-09 deposited with the CCDC.
2014-11-28 downloaded from the CCDC.
;



_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;

 ?

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         ?

_chemical_formula_sum            
'C12 H9 Eu N2 O8'

_chemical_formula_weight         461.17



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'
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'
Eu Eu -0.1578 3.6682 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'



_symmetry_cell_setting           Monoclinic

_symmetry_space_group_name_H-M   Cc



loop_

_symmetry_equiv_pos_as_xyz




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



_cell_length_a                   17.909(3)

_cell_length_b                   10.2645(15)

_cell_length_c                   7.4561(11)

_cell_angle_alpha                90.00

_cell_angle_beta                 96.9570(10)

_cell_angle_gamma                90.00

_cell_volume                     1360.5(3)

_cell_formula_units_Z            4

_cell_measurement_temperature    296(2)

_cell_measurement_reflns_used    3412

_cell_measurement_theta_min      2.29

_cell_measurement_theta_max      28.24



_exptl_crystal_description       block

_exptl_crystal_colour            yellow

_exptl_crystal_size_max          0.19

_exptl_crystal_size_mid          0.16

_exptl_crystal_size_min          0.12

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    2.251

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             888

_exptl_absorpt_coefficient_mu    4.658

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.4715

_exptl_absorpt_correction_T_max  0.6049

_exptl_absorpt_process_details   sadabs



_exptl_special_details           
;

 ?

;



_diffrn_ambient_temperature      296(2)

_diffrn_radiation_wavelength     0.71073

_diffrn_radiation_type           MoK\a

_diffrn_radiation_source         'fine-focus sealed tube'

_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'CCD area detector'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean ?

_diffrn_standards_number         0

_diffrn_standards_interval_count 0

_diffrn_standards_interval_time  0

_diffrn_standards_decay_%        0

_diffrn_reflns_number            4096

_diffrn_reflns_av_R_equivalents  0.0153

_diffrn_reflns_av_sigmaI/netI    0.0324

_diffrn_reflns_limit_h_min       -21

_diffrn_reflns_limit_h_max       20

_diffrn_reflns_limit_k_min       -12

_diffrn_reflns_limit_k_max       10

_diffrn_reflns_limit_l_min       -8

_diffrn_reflns_limit_l_max       9

_diffrn_reflns_theta_min         2.29

_diffrn_reflns_theta_max         25.49

_reflns_number_total             2296

_reflns_number_gt                2217

_reflns_threshold_expression     >2sigma(I)



_computing_data_collection       'Bruker SMART'

_computing_cell_refinement       'Bruker SMART'

_computing_data_reduction        'Bruker SAINT'

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_computing_molecular_graphics    'Bruker SHELXTL'

_computing_publication_material  'Bruker SHELXTL'



_refine_special_details          
;

 Refinement of F² against ALL reflections.  The weighted R-factor wR and

 goodness of fit S are based on F², conventional R-factors R are based

 on F, with F set to zero for negative F². The threshold expression of

 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is

 not relevant to the choice of reflections for refinement.  R-factors based

 on F² are statistically about twice as large as those based on F, and R-

 factors based on ALL data will be even larger.

;



_refine_ls_structure_factor_coef Fsqd

_refine_ls_matrix_type           full

_refine_ls_weighting_scheme      calc

_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0179P)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    constr

_refine_ls_extinction_method     none

_refine_ls_extinction_coef       ?

_refine_ls_abs_structure_details 
'Flack H D (1983), Acta Cryst. A39, 876-881'

_refine_ls_abs_structure_Flack   0.017(13)

_refine_ls_number_reflns         2296

_refine_ls_number_parameters     208

_refine_ls_number_restraints     4

_refine_ls_R_factor_all          0.0180

_refine_ls_R_factor_gt           0.0171

_refine_ls_wR_factor_ref         0.0425

_refine_ls_wR_factor_gt          0.0419

_refine_ls_goodness_of_fit_ref   1.024

_refine_ls_restrained_S_all      1.023

_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
































Eu1 Eu 0.39782(4) 0.759689(14) 0.24976(6) 0.01408(6) Uani 1 1 d . . .
N1 N 0.52973(18) 0.8181(3) 0.1596(4) 0.0144(7) Uani 1 1 d . . .
N2 N 0.5018(2) 0.5879(3) 0.2957(4) 0.0157(7) Uani 1 1 d . . .
O1 O 0.40783(17) 0.9687(3) 0.1124(4) 0.0283(8) Uani 1 1 d . . .
O2 O 0.47218(17) 1.1281(3) -0.0061(4) 0.0221(7) Uani 1 1 d . . .
O3 O 0.36362(19) 0.5693(3) 0.3976(5) 0.0275(7) Uani 1 1 d . . .
O4 O 0.38478(17) 0.3616(3) 0.4820(4) 0.0259(7) Uani 1 1 d . . .
O5 O 0.72555(17) 0.7128(3) 0.2234(4) 0.0273(7) Uani 1 1 d D . .
H5D H 0.6997 0.6042 0.2018 0.041 Uiso 1 1 d RD . .
O6 O 0.68171(17) 0.4958(3) 0.1496(5) 0.0313(8) Uani 1 1 d D . .
O7 O 0.3142(2) 0.8465(4) 0.4533(5) 0.0371(9) Uani 1 1 d . . .
H1W H 0.3274 0.9074 0.5223 0.056 Uiso 1 1 d R . .
H2W H 0.2847 0.7964 0.4962 0.056 Uiso 1 1 d R . .
O8 O 0.27333(19) 0.7900(4) 0.0920(5) 0.0326(8) Uani 1 1 d . . .
H3W H 0.2572 0.7996 -0.0165 0.049 Uiso 1 1 d R . .
H4W H 0.2554 0.8456 0.1550 0.049 Uiso 1 1 d R . .
C1 C 0.5388(2) 0.9404(4) 0.1043(6) 0.0182(9) Uani 1 1 d . . .
C2 C 0.6088(2) 0.9912(5) 0.0802(6) 0.0248(10) Uani 1 1 d . . .
H2 H 0.6134 1.0757 0.0379 0.030 Uiso 1 1 calc R . .
C3 C 0.6714(3) 0.9136(5) 0.1203(7) 0.0299(11) Uani 1 1 d . . .
H3 H 0.7189 0.9463 0.1075 0.036 Uiso 1 1 calc R . .
C4 C 0.6637(2) 0.7876(5) 0.1793(6) 0.0199(9) Uani 1 1 d . . .
C5 C 0.5898(3) 0.7375(4) 0.1924(6) 0.0178(10) Uani 1 1 d . . .
C6 C 0.5709(2) 0.6006(4) 0.2379(5) 0.0167(9) Uani 1 1 d . . .
C7 C 0.6142(2) 0.4885(5) 0.2101(6) 0.0245(10) Uani 1 1 d . . .
C8 C 0.5840(3) 0.3666(4) 0.2377(6) 0.0265(11) Uani 1 1 d . . .
H8 H 0.6109 0.2920 0.2156 0.032 Uiso 1 1 calc R . .
C9 C 0.5142(3) 0.3551(5) 0.2978(6) 0.0245(10) Uani 1 1 d . . .
H9 H 0.4936 0.2737 0.3161 0.029 Uiso 1 1 calc R . .
C10 C 0.4757(2) 0.4690(5) 0.3302(6) 0.0205(10) Uani 1 1 d . . .
C11 C 0.4686(2) 1.0208(4) 0.0673(6) 0.0196(9) Uani 1 1 d . . .
C12 C 0.4016(2) 0.4671(4) 0.4073(6) 0.0207(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











































Eu1 O4 2.340(3) 2_564 ?
Eu1 O3 2.361(3) . ?
Eu1 O1 2.393(3) . ?
Eu1 O8 2.412(3) . ?
Eu1 O2 2.414(3) 2_575 ?
Eu1 O7 2.427(3) . ?
Eu1 N2 2.557(3) . ?
Eu1 N1 2.603(3) . ?
Eu1 C12 3.223(4) . ?
Eu1 H4W 2.7098 . ?
N1 C1 1.337(5) . ?
N1 C5 1.356(6) . ?
N2 C10 1.343(6) . ?
N2 C6 1.366(5) . ?
O1 C11 1.294(5) . ?
O2 C11 1.235(5) . ?
O2 Eu1 2.414(3) 2_574 ?
O3 C12 1.247(5) . ?
O4 C12 1.270(5) . ?
O4 Eu1 2.340(3) 2_565 ?
O5 C4 1.355(6) . ?
O5 H5D 1.2100 . ?
O6 C7 1.343(5) . ?
O6 H5D 1.2100 . ?
O7 H1W 0.8261 . ?
O7 H2W 0.8285 . ?
O8 H3W 0.8314 . ?
O8 H4W 0.8280 . ?
C1 C2 1.389(6) . ?
C1 C11 1.501(6) . ?
C2 C3 1.377(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.379(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.433(6) . ?
C5 C6 1.494(6) . ?
C6 C7 1.417(6) . ?
C7 C8 1.388(7) . ?
C8 C9 1.382(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.393(6) . ?
C9 H9 0.9300 . ?
C10 C12 1.510(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 Eu1 O3 87.30(12) 2_564 . ?
O4 Eu1 O1 96.72(12) 2_564 . ?
O3 Eu1 O1 168.23(11) . . ?
O4 Eu1 O8 70.23(11) 2_564 . ?
O3 Eu1 O8 93.31(13) . . ?
O1 Eu1 O8 77.78(12) . . ?
O4 Eu1 O2 152.40(11) 2_564 2_575 ?
O3 Eu1 O2 101.16(12) . 2_575 ?
O1 Eu1 O2 80.32(11) . 2_575 ?
O8 Eu1 O2 134.35(11) . 2_575 ?
O4 Eu1 O7 136.33(12) 2_564 . ?
O3 Eu1 O7 78.30(12) . . ?
O1 Eu1 O7 91.29(11) . . ?
O8 Eu1 O7 69.74(12) . . ?
O2 Eu1 O7 71.27(11) 2_575 . ?
O4 Eu1 N2 75.13(11) 2_564 . ?
O3 Eu1 N2 65.95(11) . . ?
O1 Eu1 N2 125.76(11) . . ?
O8 Eu1 N2 140.32(11) . . ?
O2 Eu1 N2 84.36(11) 2_575 . ?
O7 Eu1 N2 131.57(12) . . ?
O4 Eu1 N1 84.40(11) 2_564 . ?
O3 Eu1 N1 127.31(11) . . ?
O1 Eu1 N1 64.26(10) . . ?
O8 Eu1 N1 131.19(12) . . ?
O2 Eu1 N1 69.51(10) 2_575 . ?
O7 Eu1 N1 136.46(11) . . ?
N2 Eu1 N1 61.62(11) . . ?
O4 Eu1 C12 79.07(11) 2_564 . ?
O3 Eu1 C12 18.81(11) . . ?
O1 Eu1 C12 172.77(12) . . ?
O8 Eu1 C12 105.99(12) . . ?
O2 Eu1 C12 100.64(11) 2_575 . ?
O7 Eu1 C12 95.81(12) . . ?
N2 Eu1 C12 47.61(11) . . ?
N1 Eu1 C12 109.22(11) . . ?
O4 Eu1 H4W 87.6 2_564 . ?
O3 Eu1 H4W 95.9 . . ?
O1 Eu1 H4W 73.4 . . ?
O8 Eu1 H4W 17.4 . . ?
O2 Eu1 H4W 117.2 2_575 . ?
O7 Eu1 H4W 53.9 . . ?
N2 Eu1 H4W 155.0 . . ?
N1 Eu1 H4W 135.4 . . ?
C12 Eu1 H4W 112.1 . . ?
C1 N1 C5 120.3(4) . . ?
C1 N1 Eu1 116.4(3) . . ?
C5 N1 Eu1 122.5(3) . . ?
C10 N2 C6 119.7(4) . . ?
C10 N2 Eu1 112.8(3) . . ?
C6 N2 Eu1 124.4(3) . . ?
C11 O1 Eu1 126.2(3) . . ?
C11 O2 Eu1 135.0(3) . 2_574 ?
C12 O3 Eu1 123.6(3) . . ?
C12 O4 Eu1 145.4(3) . 2_565 ?
C4 O5 H5D 101.6 . . ?
C7 O6 H5D 99.2 . . ?
Eu1 O7 H1W 121.0 . . ?
Eu1 O7 H2W 119.0 . . ?
H1W O7 H2W 112.2 . . ?
Eu1 O8 H3W 133.0 . . ?
Eu1 O8 H4W 102.2 . . ?
H3W O8 H4W 111.0 . . ?
N1 C1 C2 122.5(4) . . ?
N1 C1 C11 116.2(4) . . ?
C2 C1 C11 121.3(4) . . ?
C3 C2 C1 118.5(4) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C2 C3 C4 120.1(4) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
O5 C4 C3 119.9(4) . . ?
O5 C4 C5 121.0(4) . . ?
C3 C4 C5 119.1(4) . . ?
N1 C5 C4 119.2(4) . . ?
N1 C5 C6 114.8(4) . . ?
C4 C5 C6 126.1(4) . . ?
N2 C6 C7 120.1(4) . . ?
N2 C6 C5 113.6(4) . . ?
C7 C6 C5 126.0(4) . . ?
O6 C7 C8 118.9(4) . . ?
O6 C7 C6 122.3(4) . . ?
C8 C7 C6 118.7(4) . . ?
C7 C8 C9 120.6(4) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C10 C9 C8 118.0(4) . . ?
C10 C9 H9 121.0 . . ?
C8 C9 H9 121.0 . . ?
N2 C10 C9 122.6(4) . . ?
N2 C10 C12 115.3(4) . . ?
C9 C10 C12 122.1(4) . . ?
O2 C11 O1 125.0(4) . . ?
O2 C11 C1 119.0(4) . . ?
O1 C11 C1 116.0(4) . . ?
O3 C12 O4 125.8(4) . . ?
O3 C12 C10 117.7(4) . . ?
O4 C12 C10 116.4(4) . . ?
O3 C12 Eu1 37.6(2) . . ?
O4 C12 Eu1 163.4(3) . . ?
C10 C12 Eu1 80.2(2) . . ?



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































































































































O4 Eu1 N1 C1 108.5(3) 2_564 . . . ?
O3 Eu1 N1 C1 -169.2(3) . . . . ?
O1 Eu1 N1 C1 8.3(3) . . . . ?
O8 Eu1 N1 C1 51.0(3) . . . . ?
O2 Eu1 N1 C1 -80.6(3) 2_575 . . . ?
O7 Eu1 N1 C1 -53.6(3) . . . . ?
N2 Eu1 N1 C1 -175.4(3) . . . . ?
C12 Eu1 N1 C1 -175.1(3) . . . . ?
O4 Eu1 N1 C5 -81.5(3) 2_564 . . . ?
O3 Eu1 N1 C5 0.8(4) . . . . ?
O1 Eu1 N1 C5 178.2(3) . . . . ?
O8 Eu1 N1 C5 -139.0(3) . . . . ?
O2 Eu1 N1 C5 89.3(3) 2_575 . . . ?
O7 Eu1 N1 C5 116.3(3) . . . . ?
N2 Eu1 N1 C5 -5.4(3) . . . . ?
C12 Eu1 N1 C5 -5.2(3) . . . . ?
O4 Eu1 N2 C10 -75.6(3) 2_564 . . . ?
O3 Eu1 N2 C10 18.2(3) . . . . ?
O1 Eu1 N2 C10 -163.1(3) . . . . ?
O8 Eu1 N2 C10 -45.8(3) . . . . ?
O2 Eu1 N2 C10 123.1(3) 2_575 . . . ?
O7 Eu1 N2 C10 64.3(3) . . . . ?
N1 Eu1 N2 C10 -167.2(3) . . . . ?
C12 Eu1 N2 C10 13.1(2) . . . . ?
O4 Eu1 N2 C6 84.7(3) 2_564 . . . ?
O3 Eu1 N2 C6 178.5(3) . . . . ?
O1 Eu1 N2 C6 -2.9(4) . . . . ?
O8 Eu1 N2 C6 114.5(3) . . . . ?
O2 Eu1 N2 C6 -76.6(3) 2_575 . . . ?
O7 Eu1 N2 C6 -135.4(3) . . . . ?
N1 Eu1 N2 C6 -6.9(3) . . . . ?
C12 Eu1 N2 C6 173.4(4) . . . . ?
O4 Eu1 O1 C11 -84.9(4) 2_564 . . . ?
O3 Eu1 O1 C11 165.6(5) . . . . ?
O8 Eu1 O1 C11 -153.0(4) . . . . ?
O2 Eu1 O1 C11 67.3(3) 2_575 . . . ?
O7 Eu1 O1 C11 138.1(3) . . . . ?
N2 Eu1 O1 C11 -8.4(4) . . . . ?
N1 Eu1 O1 C11 -4.5(3) . . . . ?
C12 Eu1 O1 C11 -30.9(12) . . . . ?
O4 Eu1 O3 C12 63.3(4) 2_564 . . . ?
O1 Eu1 O3 C12 173.6(6) . . . . ?
O8 Eu1 O3 C12 133.3(4) . . . . ?
O2 Eu1 O3 C12 -90.2(4) 2_575 . . . ?
O7 Eu1 O3 C12 -158.2(4) . . . . ?
N2 Eu1 O3 C12 -11.6(3) . . . . ?
N1 Eu1 O3 C12 -17.6(4) . . . . ?
C5 N1 C1 C2 -0.9(6) . . . . ?
Eu1 N1 C1 C2 169.3(3) . . . . ?
C5 N1 C1 C11 178.5(4) . . . . ?
Eu1 N1 C1 C11 -11.3(5) . . . . ?
N1 C1 C2 C3 -2.1(7) . . . . ?
C11 C1 C2 C3 178.6(4) . . . . ?
C1 C2 C3 C4 1.3(7) . . . . ?
C2 C3 C4 O5 -178.1(4) . . . . ?
C2 C3 C4 C5 2.1(7) . . . . ?
C1 N1 C5 C4 4.3(6) . . . . ?
Eu1 N1 C5 C4 -165.2(3) . . . . ?
C1 N1 C5 C6 -175.0(4) . . . . ?
Eu1 N1 C5 C6 15.4(5) . . . . ?
O5 C4 C5 N1 175.3(4) . . . . ?
C3 C4 C5 N1 -5.0(7) . . . . ?
O5 C4 C5 C6 -5.5(7) . . . . ?
C3 C4 C5 C6 174.3(4) . . . . ?
C10 N2 C6 C7 1.5(6) . . . . ?
Eu1 N2 C6 C7 -157.5(3) . . . . ?
C10 N2 C6 C5 175.8(4) . . . . ?
Eu1 N2 C6 C5 16.7(5) . . . . ?
N1 C5 C6 N2 -20.0(5) . . . . ?
C4 C5 C6 N2 160.7(4) . . . . ?
N1 C5 C6 C7 153.9(4) . . . . ?
C4 C5 C6 C7 -25.4(7) . . . . ?
N2 C6 C7 O6 178.5(4) . . . . ?
C5 C6 C7 O6 5.0(7) . . . . ?
N2 C6 C7 C8 1.9(6) . . . . ?
C5 C6 C7 C8 -171.6(4) . . . . ?
O6 C7 C8 C9 -179.2(4) . . . . ?
C6 C7 C8 C9 -2.5(7) . . . . ?
C7 C8 C9 C10 -0.2(7) . . . . ?
C6 N2 C10 C9 -4.4(6) . . . . ?
Eu1 N2 C10 C9 156.9(3) . . . . ?
C6 N2 C10 C12 175.4(3) . . . . ?
Eu1 N2 C10 C12 -23.3(4) . . . . ?
C8 C9 C10 N2 3.8(7) . . . . ?
C8 C9 C10 C12 -176.0(4) . . . . ?
Eu1 O2 C11 O1 -44.0(6) 2_574 . . . ?
Eu1 O2 C11 C1 134.2(3) 2_574 . . . ?
Eu1 O1 C11 O2 178.8(3) . . . . ?
Eu1 O1 C11 C1 0.6(5) . . . . ?
N1 C1 C11 O2 -170.7(4) . . . . ?
C2 C1 C11 O2 8.7(6) . . . . ?
N1 C1 C11 O1 7.7(6) . . . . ?
C2 C1 C11 O1 -172.9(4) . . . . ?
Eu1 O3 C12 O4 -178.5(3) . . . . ?
Eu1 O3 C12 C10 4.0(5) . . . . ?
Eu1 O4 C12 O3 -91.5(6) 2_565 . . . ?
Eu1 O4 C12 C10 86.0(6) 2_565 . . . ?
Eu1 O4 C12 Eu1 -94.7(11) 2_565 . . . ?
N2 C10 C12 O3 14.6(6) . . . . ?
C9 C10 C12 O3 -165.6(4) . . . . ?
N2 C10 C12 O4 -163.1(4) . . . . ?
C9 C10 C12 O4 16.7(6) . . . . ?
N2 C10 C12 Eu1 17.1(3) . . . . ?
C9 C10 C12 Eu1 -163.1(4) . . . . ?
O4 Eu1 C12 O3 -114.7(4) 2_564 . . . ?
O1 Eu1 C12 O3 -169.7(9) . . . . ?
O8 Eu1 C12 O3 -49.1(4) . . . . ?
O2 Eu1 C12 O3 93.4(4) 2_575 . . . ?
O7 Eu1 C12 O3 21.4(4) . . . . ?
N2 Eu1 C12 O3 165.5(4) . . . . ?
N1 Eu1 C12 O3 165.3(4) . . . . ?
O4 Eu1 C12 O4 -110.5(11) 2_564 . . . ?
O3 Eu1 C12 O4 4.2(9) . . . . ?
O1 Eu1 C12 O4 -165.4(9) . . . . ?
O8 Eu1 C12 O4 -44.9(11) . . . . ?
O2 Eu1 C12 O4 97.6(10) 2_575 . . . ?
O7 Eu1 C12 O4 25.6(10) . . . . ?
N2 Eu1 C12 O4 169.8(11) . . . . ?
N1 Eu1 C12 O4 169.5(10) . . . . ?
O4 Eu1 C12 C10 68.9(2) 2_564 . . . ?
O3 Eu1 C12 C10 -176.4(5) . . . . ?
O1 Eu1 C12 C10 13.9(11) . . . . ?
O8 Eu1 C12 C10 134.4(2) . . . . ?
O2 Eu1 C12 C10 -83.0(2) 2_575 . . . ?
O7 Eu1 C12 C10 -155.0(2) . . . . ?
N2 Eu1 C12 C10 -10.9(2) . . . . ?
N1 Eu1 C12 C10 -11.2(2) . . . . ?



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






O5 H5D O6 1.21 1.21 2.4035(12) 166.6 .
O7 H1W O1 0.83 1.98 2.709(4) 147.3 2_575
O7 H2W O5 0.83 2.11 2.779(5) 138.1 4_465
O8 H3W O5 0.83 1.96 2.778(5) 168.9 4_464
O8 H4W O6 0.83 2.03 2.740(4) 144.0 3_455
O8 H4W O7 0.83 2.34 2.766(5) 112.4 .



_diffrn_measured_fraction_theta_max 0.998

_diffrn_reflns_theta_full        25.49

_diffrn_measured_fraction_theta_full 0.998

_refine_diff_density_max         0.431

_refine_diff_density_min         -0.889

_refine_diff_density_rms         0.091

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

data_5
_database_code_depnum_ccdc_archive 'CCDC 975873'
_audit_update_record             
;
2013-12-09 deposited with the CCDC.
2014-11-28 downloaded from the CCDC.
;



_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;

 ?

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         ?

_chemical_formula_sum            
'C12 H9 Gd N2 O8'

_chemical_formula_weight         466.46



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'
Gd Gd -0.1653 3.9035 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'



_symmetry_cell_setting           Monoclinic

_symmetry_space_group_name_H-M   Cc



loop_

_symmetry_equiv_pos_as_xyz




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



_cell_length_a                   17.858(3)

_cell_length_b                   10.2355(15)

_cell_length_c                   7.4678(11)

_cell_angle_alpha                90.00

_cell_angle_beta                 96.909(2)

_cell_angle_gamma                90.00

_cell_volume                     1355.1(3)

_cell_formula_units_Z            4

_cell_measurement_temperature    296(2)

_cell_measurement_reflns_used    4462

_cell_measurement_theta_min      2.30

_cell_measurement_theta_max      28.21



_exptl_crystal_description       block

_exptl_crystal_colour            yellow

_exptl_crystal_size_max          0.38

_exptl_crystal_size_mid          0.24

_exptl_crystal_size_min          0.16

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    2.286

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             892

_exptl_absorpt_coefficient_mu    4.942

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.2553

_exptl_absorpt_correction_T_max  0.5052

_exptl_absorpt_process_details   sadabs



_exptl_special_details           
;

 ?

;



_diffrn_ambient_temperature      296(2)

_diffrn_radiation_wavelength     0.71073

_diffrn_radiation_type           MoK\a

_diffrn_radiation_source         'fine-focus sealed tube'

_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'CCD area detector'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean ?

_diffrn_standards_number         0

_diffrn_standards_interval_count ?

_diffrn_standards_interval_time  ?

_diffrn_standards_decay_%        ?

_diffrn_reflns_number            4382

_diffrn_reflns_av_R_equivalents  0.0151

_diffrn_reflns_av_sigmaI/netI    0.0326

_diffrn_reflns_limit_h_min       -21

_diffrn_reflns_limit_h_max       21

_diffrn_reflns_limit_k_min       -12

_diffrn_reflns_limit_k_max       12

_diffrn_reflns_limit_l_min       -9

_diffrn_reflns_limit_l_max       9

_diffrn_reflns_theta_min         2.30

_diffrn_reflns_theta_max         25.50

_reflns_number_total             2425

_reflns_number_gt                2377

_reflns_threshold_expression     >2sigma(I)



_computing_data_collection       'Bruker SMART'

_computing_cell_refinement       'Bruker SMART'

_computing_data_reduction        'Bruker SAINT'

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_computing_molecular_graphics    'Bruker SHELXTL'

_computing_publication_material  'Bruker SHELXTL'



_refine_special_details          
;

 Refinement of F² against ALL reflections.  The weighted R-factor wR and

 goodness of fit S are based on F², conventional R-factors R are based

 on F, with F set to zero for negative F². The threshold expression of

 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is

 not relevant to the choice of reflections for refinement.  R-factors based

 on F² are statistically about twice as large as those based on F, and R-

 factors based on ALL data will be even larger.

;



_refine_ls_structure_factor_coef Fsqd

_refine_ls_matrix_type           full

_refine_ls_weighting_scheme      calc

_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0575P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_primary     direct

_atom_sites_solution_secondary   difmap

_atom_sites_solution_hydrogens   geom

_refine_ls_hydrogen_treatment    constr

_refine_ls_extinction_method     none

_refine_ls_extinction_coef       ?

_refine_ls_abs_structure_details 
'Flack H D (1983), Acta Cryst. A39, 876-881'

_refine_ls_abs_structure_Flack   0.027(11)

_refine_ls_number_reflns         2425

_refine_ls_number_parameters     208

_refine_ls_number_restraints     2

_refine_ls_R_factor_all          0.0188

_refine_ls_R_factor_gt           0.0185

_refine_ls_wR_factor_ref         0.0533

_refine_ls_wR_factor_gt          0.0520

_refine_ls_goodness_of_fit_ref   0.488

_refine_ls_restrained_S_all      0.488

_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
































Gd1 Gd 0.94265(4) 0.740174(12) -0.01167(8) 0.01307(8) Uani 1 1 d . . .
O1 O 0.97760(16) 0.9304(3) -0.1607(4) 0.0270(6) Uani 1 1 d . . .
O2 O 0.95598(15) 1.1374(3) -0.2467(3) 0.0250(6) Uani 1 1 d . . .
O3 O 0.65825(16) 1.0039(3) 0.0872(4) 0.0305(7) Uani 1 1 d . . .
H3D H 0.6284 0.8993 0.0525 0.046 Uiso 1 1 d R . .
O4 O 0.6146(2) 0.7851(4) 0.0150(5) 0.0276(7) Uani 1 1 d . . .
O5 O 0.86927(15) 0.3711(3) 0.2439(4) 0.0231(6) Uani 1 1 d . . .
O6 O 0.93354(15) 0.5299(3) 0.1257(4) 0.0271(7) Uani 1 1 d . . .
O7 O 1.0672(2) 0.7106(4) 0.1458(5) 0.0316(7) Uani 1 1 d . . .
H1W H 1.0913 0.6479 0.1048 0.047 Uiso 1 1 d R . .
H2W H 1.0700 0.7262 0.2582 0.047 Uiso 1 1 d R . .
O8 O 1.02742(16) 0.6527(4) -0.2112(4) 0.0350(8) Uani 1 1 d . . .
H3W H 1.0594 0.6848 -0.2743 0.052 Uiso 1 1 d R . .
H4W H 1.0018 0.6016 -0.2845 0.052 Uiso 1 1 d R . .
N1 N 0.83840(17) 0.9107(3) -0.0581(4) 0.0149(6) Uani 1 1 d . . .
N2 N 0.81098(16) 0.6810(3) 0.0776(4) 0.0139(6) Uani 1 1 d . . .
C1 C 0.8643(2) 1.0304(4) -0.0929(4) 0.0175(7) Uani 1 1 d . . .
C2 C 0.8260(2) 1.1450(4) -0.0618(5) 0.0232(8) Uani 1 1 d . . .
H2 H 0.8465 1.2266 -0.0807 0.028 Uiso 1 1 calc R . .
C3 C 0.7556(2) 1.1326(4) -0.0014(5) 0.0261(9) Uani 1 1 d . . .
H3A H 0.7282 1.2070 0.0204 0.031 Uiso 1 1 calc R . .
C4 C 0.72583(19) 1.0095(4) 0.0266(5) 0.0218(8) Uani 1 1 d . . .
C5 C 0.76964(18) 0.8979(4) 0.0000(4) 0.0149(7) Uani 1 1 d . . .
C6 C 0.7503(3) 0.7617(4) 0.0451(8) 0.0177(11) Uani 1 1 d . . .
C7 C 0.6763(2) 0.7118(5) 0.0587(6) 0.0198(8) Uani 1 1 d . . .
C8 C 0.6689(2) 0.5847(5) 0.1183(6) 0.0286(9) Uani 1 1 d . . .
H8 H 0.6213 0.5519 0.1315 0.034 Uiso 1 1 calc R . .
C9 C 0.7318(2) 0.5064(4) 0.1581(5) 0.0249(8) Uani 1 1 d . . .
H9 H 0.7275 0.4216 0.2004 0.030 Uiso 1 1 calc R . .
C10 C 0.80172(19) 0.5585(4) 0.1329(4) 0.0161(7) Uani 1 1 d . . .
C11 C 0.9389(2) 1.0313(4) -0.1715(5) 0.0200(8) Uani 1 1 d . . .
C12 C 0.87288(19) 0.4790(4) 0.1701(4) 0.0191(8) 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 O2 2.330(3) 2_575 ?
Gd1 O1 2.364(3) . ?
Gd1 O6 2.398(3) . ?
Gd1 O5 2.402(3) 2_564 ?
Gd1 O7 2.407(4) . ?
Gd1 O8 2.420(3) . ?
Gd1 N1 2.545(3) . ?
Gd1 N2 2.592(3) . ?
O1 C11 1.240(5) . ?
O2 C11 1.275(4) . ?
O2 Gd1 2.330(3) 2_574 ?
O3 C4 1.340(4) . ?
O3 H3D 1.2107 . ?
O4 C7 1.341(6) . ?
O4 H3D 1.2205 . ?
O5 C12 1.240(5) . ?
O5 Gd1 2.402(3) 2_565 ?
O6 C12 1.281(4) . ?
O7 H1W 0.8500 . ?
O7 H2W 0.8499 . ?
O8 H3W 0.8500 . ?
O8 H4W 0.8500 . ?
N1 C1 1.346(5) . ?
N1 C5 1.357(4) . ?
N2 C10 1.336(5) . ?
N2 C6 1.361(6) . ?
C1 C2 1.392(6) . ?
C1 C11 1.518(5) . ?
C2 C3 1.391(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.393(6) . ?
C3 H3A 0.9300 . ?
C4 C5 1.411(5) . ?
C5 C6 1.485(5) . ?
C6 C7 1.432(7) . ?
C7 C8 1.387(7) . ?
C8 C9 1.383(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.391(5) . ?
C9 H9 0.9300 . ?
C10 C12 1.506(5) . ?



loop_

_geom_angle_atom_site_label_1

_geom_angle_atom_site_label_2

_geom_angle_atom_site_label_3

_geom_angle

_geom_angle_site_symmetry_1

_geom_angle_site_symmetry_3

_geom_angle_publ_flag


















































































O2 Gd1 O1 87.18(11) 2_575 . ?
O2 Gd1 O6 97.17(11) 2_575 . ?
O1 Gd1 O6 167.45(11) . . ?
O2 Gd1 O5 152.99(11) 2_575 2_564 ?
O1 Gd1 O5 100.58(12) . 2_564 ?
O6 Gd1 O5 80.83(10) . 2_564 ?
O2 Gd1 O7 70.05(11) 2_575 . ?
O1 Gd1 O7 93.04(13) . . ?
O6 Gd1 O7 77.53(13) . . ?
O5 Gd1 O7 134.36(11) 2_564 . ?
O2 Gd1 O8 135.58(12) 2_575 . ?
O1 Gd1 O8 78.16(12) . . ?
O6 Gd1 O8 90.62(11) . . ?
O5 Gd1 O8 71.41(10) 2_564 . ?
O7 Gd1 O8 69.17(11) . . ?
O2 Gd1 N1 75.23(9) 2_575 . ?
O1 Gd1 N1 66.49(9) . . ?
O6 Gd1 N1 126.00(11) . . ?
O5 Gd1 N1 84.17(10) 2_564 . ?
O7 Gd1 N1 140.42(12) . . ?
O8 Gd1 N1 132.18(12) . . ?
O2 Gd1 N2 84.86(10) 2_575 . ?
O1 Gd1 N2 127.80(10) . . ?
O6 Gd1 N2 64.52(9) . . ?
O5 Gd1 N2 69.87(9) 2_564 . ?
O7 Gd1 N2 131.18(12) . . ?
O8 Gd1 N2 136.55(10) . . ?
N1 Gd1 N2 61.58(10) . . ?
C11 O1 Gd1 122.7(2) . . ?
C11 O2 Gd1 145.7(2) . 2_574 ?
C4 O3 H3D 110.9 . . ?
C7 O4 H3D 110.0 . . ?
C12 O5 Gd1 135.0(2) . 2_565 ?
C12 O6 Gd1 125.3(2) . . ?
Gd1 O7 H1W 113.5 . . ?
Gd1 O7 H2W 113.6 . . ?
H1W O7 H2W 121.7 . . ?
Gd1 O8 H3W 135.3 . . ?
Gd1 O8 H4W 107.3 . . ?
H3W O8 H4W 103.1 . . ?
C1 N1 C5 119.7(3) . . ?
C1 N1 Gd1 112.8(2) . . ?
C5 N1 Gd1 124.4(2) . . ?
C10 N2 C6 120.0(3) . . ?
C10 N2 Gd1 116.7(2) . . ?
C6 N2 Gd1 122.6(3) . . ?
N1 C1 C2 123.1(3) . . ?
N1 C1 C11 114.8(3) . . ?
C2 C1 C11 122.1(3) . . ?
C3 C2 C1 117.4(4) . . ?
C3 C2 H2 121.3 . . ?
C1 C2 H2 121.3 . . ?
C2 C3 C4 120.5(4) . . ?
C2 C3 H3A 119.8 . . ?
C4 C3 H3A 119.8 . . ?
O3 C4 C3 117.7(4) . . ?
O3 C4 C5 123.4(4) . . ?
C3 C4 C5 118.9(3) . . ?
N1 C5 C4 120.3(3) . . ?
N1 C5 C6 114.0(4) . . ?
C4 C5 C6 125.5(4) . . ?
N2 C6 C7 119.5(4) . . ?
N2 C6 C5 114.2(5) . . ?
C7 C6 C5 126.4(4) . . ?
O4 C7 C8 119.7(4) . . ?
O4 C7 C6 121.5(4) . . ?
C8 C7 C6 118.9(4) . . ?
C9 C8 C7 120.4(4) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 117.9(4) . . ?
C8 C9 H9 121.1 . . ?
C10 C9 H9 121.1 . . ?
N2 C10 C9 123.2(3) . . ?
N2 C10 C12 115.5(3) . . ?
C9 C10 C12 121.3(3) . . ?
O1 C11 O2 125.2(3) . . ?
O1 C11 C1 118.5(3) . . ?
O2 C11 C1 116.3(3) . . ?
O5 C12 O6 124.6(3) . . ?
O5 C12 C10 118.4(3) . . ?
O6 C12 C10 117.0(3) . . ?



loop_

_geom_torsion_atom_site_label_1

_geom_torsion_atom_site_label_2

_geom_torsion_atom_site_label_3

_geom_torsion_atom_site_label_4

_geom_torsion

_geom_torsion_site_symmetry_1

_geom_torsion_site_symmetry_2

_geom_torsion_site_symmetry_3

_geom_torsion_site_symmetry_4

_geom_torsion_publ_flag
































































































O2 Gd1 O1 C11 -64.1(3) 2_575 . . . ?
O6 Gd1 O1 C11 -174.8(5) . . . . ?
O5 Gd1 O1 C11 89.8(3) 2_564 . . . ?
O7 Gd1 O1 C11 -134.0(3) . . . . ?
O8 Gd1 O1 C11 158.1(3) . . . . ?
N1 Gd1 O1 C11 11.0(3) . . . . ?
N2 Gd1 O1 C11 17.2(4) . . . . ?
O2 Gd1 O6 C12 85.0(3) 2_575 . . . ?
O1 Gd1 O6 C12 -165.3(5) . . . . ?
O5 Gd1 O6 C12 -67.8(3) 2_564 . . . ?
O7 Gd1 O6 C12 152.7(3) . . . . ?
O8 Gd1 O6 C12 -138.8(3) . . . . ?
N1 Gd1 O6 C12 8.1(3) . . . . ?
N2 Gd1 O6 C12 4.2(3) . . . . ?
O2 Gd1 N1 C1 75.1(2) 2_575 . . . ?
O1 Gd1 N1 C1 -18.3(2) . . . . ?
O6 Gd1 N1 C1 163.3(2) . . . . ?
O5 Gd1 N1 C1 -122.5(2) 2_564 . . . ?
O7 Gd1 N1 C1 45.9(3) . . . . ?
O8 Gd1 N1 C1 -64.2(3) . . . . ?
N2 Gd1 N1 C1 167.2(2) . . . . ?
O2 Gd1 N1 C5 -84.9(3) 2_575 . . . ?
O1 Gd1 N1 C5 -178.3(3) . . . . ?
O6 Gd1 N1 C5 3.3(3) . . . . ?
O5 Gd1 N1 C5 77.5(3) 2_564 . . . ?
O7 Gd1 N1 C5 -114.1(3) . . . . ?
O8 Gd1 N1 C5 135.9(2) . . . . ?
N2 Gd1 N1 C5 7.3(2) . . . . ?
O2 Gd1 N2 C10 -108.8(2) 2_575 . . . ?
O1 Gd1 N2 C10 168.8(2) . . . . ?
O6 Gd1 N2 C10 -8.3(2) . . . . ?
O5 Gd1 N2 C10 80.9(2) 2_564 . . . ?
O7 Gd1 N2 C10 -51.0(3) . . . . ?
O8 Gd1 N2 C10 52.7(3) . . . . ?
N1 Gd1 N2 C10 175.3(3) . . . . ?
O2 Gd1 N2 C6 81.2(4) 2_575 . . . ?
O1 Gd1 N2 C6 -1.2(4) . . . . ?
O6 Gd1 N2 C6 -178.4(4) . . . . ?
O5 Gd1 N2 C6 -89.1(4) 2_564 . . . ?
O7 Gd1 N2 C6 138.9(3) . . . . ?
O8 Gd1 N2 C6 -117.4(4) . . . . ?
N1 Gd1 N2 C6 5.2(3) . . . . ?
C5 N1 C1 C2 4.1(5) . . . . ?
Gd1 N1 C1 C2 -156.9(3) . . . . ?
C5 N1 C1 C11 -175.2(3) . . . . ?
Gd1 N1 C1 C11 23.8(3) . . . . ?
N1 C1 C2 C3 -3.7(5) . . . . ?
C11 C1 C2 C3 175.5(3) . . . . ?
C1 C2 C3 C4 0.2(5) . . . . ?
C2 C3 C4 O3 179.1(3) . . . . ?
C2 C3 C4 C5 2.7(5) . . . . ?
C1 N1 C5 C4 -0.9(4) . . . . ?
Gd1 N1 C5 C4 157.7(2) . . . . ?
C1 N1 C5 C6 -176.0(4) . . . . ?
Gd1 N1 C5 C6 -17.4(4) . . . . ?
O3 C4 C5 N1 -178.6(3) . . . . ?
C3 C4 C5 N1 -2.4(5) . . . . ?
O3 C4 C5 C6 -4.1(6) . . . . ?
C3 C4 C5 C6 172.2(4) . . . . ?
C10 N2 C6 C7 -4.2(7) . . . . ?
Gd1 N2 C6 C7 165.6(3) . . . . ?
C10 N2 C6 C5 175.0(4) . . . . ?
Gd1 N2 C6 C5 -15.3(6) . . . . ?
N1 C5 C6 N2 20.2(6) . . . . ?
C4 C5 C6 N2 -154.6(4) . . . . ?
N1 C5 C6 C7 -160.7(5) . . . . ?
C4 C5 C6 C7 24.5(8) . . . . ?
N2 C6 C7 O4 -175.0(4) . . . . ?
C5 C6 C7 O4 5.9(8) . . . . ?
N2 C6 C7 C8 4.8(7) . . . . ?
C5 C6 C7 C8 -174.2(5) . . . . ?
O4 C7 C8 C9 177.8(4) . . . . ?
C6 C7 C8 C9 -2.1(7) . . . . ?
C7 C8 C9 C10 -1.3(6) . . . . ?
C6 N2 C10 C9 0.7(6) . . . . ?
Gd1 N2 C10 C9 -169.6(3) . . . . ?
C6 N2 C10 C12 -178.3(4) . . . . ?
Gd1 N2 C10 C12 11.4(4) . . . . ?
C8 C9 C10 N2 2.1(6) . . . . ?
C8 C9 C10 C12 -179.0(3) . . . . ?
Gd1 O1 C11 O2 178.3(3) . . . . ?
Gd1 O1 C11 C1 -2.8(4) . . . . ?
Gd1 O2 C11 O1 93.3(5) 2_574 . . . ?
Gd1 O2 C11 C1 -85.6(5) 2_574 . . . ?
N1 C1 C11 O1 -15.7(4) . . . . ?
C2 C1 C11 O1 165.0(4) . . . . ?
N1 C1 C11 O2 163.3(3) . . . . ?
C2 C1 C11 O2 -16.0(5) . . . . ?
Gd1 O5 C12 O6 44.7(5) 2_565 . . . ?
Gd1 O5 C12 C10 -133.9(3) 2_565 . . . ?
Gd1 O6 C12 O5 -178.7(3) . . . . ?
Gd1 O6 C12 C10 -0.1(4) . . . . ?
N2 C10 C12 O5 170.7(3) . . . . ?
C9 C10 C12 O5 -8.3(5) . . . . ?
N2 C10 C12 O6 -8.0(5) . . . . ?
C9 C10 C12 O6 173.0(3) . . . . ?



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




O8 H4W O6 0.85 1.88 2.701(4) 160.7 2_564
O8 H3W O4 0.85 1.98 2.789(5) 159.1 4_564
O7 H2W O4 0.85 1.99 2.785(5) 155.5 4_565
O7 H1W O3 0.85 1.91 2.735(5) 162.7 3_545



_diffrn_measured_fraction_theta_max 0.999

_diffrn_reflns_theta_full        25.50

_diffrn_measured_fraction_theta_full 0.999

_refine_diff_density_max         0.427

_refine_diff_density_min         -1.232

_refine_diff_density_rms         0.135

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

data_6
_database_code_depnum_ccdc_archive 'CCDC 975874'
_audit_update_record             
;
2013-12-09 deposited with the CCDC.
2014-11-28 downloaded from the CCDC.
;



_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;

 ?

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         ?

_chemical_formula_sum            
'C12 H9 N2 O8 Tb'

_chemical_formula_weight         468.13



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'
Tb Tb -0.1723 4.1537 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'



_symmetry_cell_setting           Orthorhombic

_symmetry_space_group_name_H-M   Pbcn



loop_

_symmetry_equiv_pos_as_xyz








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



_cell_length_a                   8.4886(11)

_cell_length_b                   20.972(3)

_cell_length_c                   8.0409(10)

_cell_angle_alpha                90.00

_cell_angle_beta                 90.00

_cell_angle_gamma                90.00

_cell_volume                     1431.4(3)

_cell_formula_units_Z            4

_cell_measurement_temperature    293(2)

_cell_measurement_reflns_used    5194

_cell_measurement_theta_min      2.59

_cell_measurement_theta_max      28.20



_exptl_crystal_description       block

_exptl_crystal_colour            yellow

_exptl_crystal_size_max          0.21

_exptl_crystal_size_mid          0.15

_exptl_crystal_size_min          0.10

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    2.172

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             896

_exptl_absorpt_coefficient_mu    4.986

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.4207

_exptl_absorpt_correction_T_max  0.6355

_exptl_absorpt_process_details   sadabs



_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  'CCD area detector'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean ?

_diffrn_standards_number         0

_diffrn_standards_interval_count 0

_diffrn_standards_interval_time  0

_diffrn_standards_decay_%        0

_diffrn_reflns_number            9879

_diffrn_reflns_av_R_equivalents  0.0232

_diffrn_reflns_av_sigmaI/netI    0.0147

_diffrn_reflns_limit_h_min       -10

_diffrn_reflns_limit_h_max       10

_diffrn_reflns_limit_k_min       -25

_diffrn_reflns_limit_k_max       24

_diffrn_reflns_limit_l_min       -9

_diffrn_reflns_limit_l_max       9

_diffrn_reflns_theta_min         2.59

_diffrn_reflns_theta_max         25.49

_reflns_number_total             1335

_reflns_number_gt                1143

_reflns_threshold_expression     >2sigma(I)



_computing_data_collection       'Bruker SMART'

_computing_cell_refinement       'Bruker SMART'

_computing_data_reduction        'Bruker SAINT'

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_computing_molecular_graphics    'Bruker SHELXTL'

_computing_publication_material  'Bruker SHELXTL'



_refine_special_details          
;

 Refinement of F² against ALL reflections.  The weighted R-factor wR and

 goodness of fit S are based on F², conventional R-factors R are based

 on F, with F set to zero for negative F². The threshold expression of

 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is

 not relevant to the choice of reflections for refinement.  R-factors based

 on F² are statistically about twice as large as those based on F, and R-

 factors based on ALL data will be even larger.

;



_refine_ls_structure_factor_coef Fsqd

_refine_ls_matrix_type           full

_refine_ls_weighting_scheme      calc

_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0201P)²+2.1972P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_primary     direct

_atom_sites_solution_secondary   difmap

_atom_sites_solution_hydrogens   geom

_refine_ls_hydrogen_treatment    constr

_refine_ls_extinction_method     none

_refine_ls_extinction_coef       ?

_refine_ls_number_reflns         1335

_refine_ls_number_parameters     105

_refine_ls_number_restraints     0

_refine_ls_R_factor_all          0.0211

_refine_ls_R_factor_gt           0.0168

_refine_ls_wR_factor_ref         0.0420

_refine_ls_wR_factor_gt          0.0397

_refine_ls_goodness_of_fit_ref   1.036

_refine_ls_restrained_S_all      1.036

_refine_ls_shift/su_max          0.000

_refine_ls_shift/su_mean         0.000



loop_

_atom_site_label

_atom_site_type_symbol

_atom_site_fract_x

_atom_site_fract_y

_atom_site_fract_z

_atom_site_U_iso_or_equiv

_atom_site_adp_type

_atom_site_occupancy

_atom_site_symmetry_multiplicity

_atom_site_calc_flag

_atom_site_refinement_flags

_atom_site_disorder_assembly

_atom_site_disorder_group

















Tb1 Tb 0.0000 0.211101(8) 0.7500 0.01589(8) Uani 1 2 d S . .
N1 N 0.1220(3) 0.10947(10) 0.6480(3) 0.0180(5) Uani 1 1 d . . .
O1 O 0.2079(3) 0.22805(10) 0.5746(3) 0.0399(6) Uani 1 1 d . . .
O2 O 0.3853(2) 0.19593(10) 0.3884(3) 0.0293(5) Uani 1 1 d . . .
O3 O 0.1091(2) -0.06383(9) 0.6574(3) 0.0292(5) Uani 1 1 d . . .
H3D H -0.0001 -0.0666 0.7501 0.044 Uiso 1 2 d SR . .
O4 O -0.1535(3) 0.16966(10) 0.5306(3) 0.0461(7) Uani 1 1 d . . .
H1W H -0.1359 0.1372 0.4756 0.069 Uiso 1 1 d R . .
H2W H -0.2087 0.1956 0.4796 0.069 Uiso 1 1 d R . .
C1 C 0.2431(3) 0.11730(13) 0.5422(3) 0.0206(6) Uani 1 1 d . . .
C2 C 0.3245(3) 0.06591(14) 0.4753(4) 0.0264(6) Uani 1 1 d . . .
H2 H 0.4082 0.0722 0.4026 0.032 Uiso 1 1 calc R . .
C3 C 0.2779(4) 0.00562(13) 0.5197(3) 0.0256(6) Uani 1 1 d . . .
H3A H 0.3324 -0.0294 0.4782 0.031 Uiso 1 1 calc R . .
C4 C 0.1499(3) -0.00401(12) 0.6262(3) 0.0210(6) Uani 1 1 d . . .
C5 C 0.0706(3) 0.05088(13) 0.6920(3) 0.0171(5) Uani 1 1 d . . .
C6 C 0.2834(3) 0.18491(13) 0.4972(4) 0.0248(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

























Tb1 O1 2.286(2) . ?
Tb1 O1 2.286(2) 4_556 ?
Tb1 O4 2.359(2) . ?
Tb1 O4 2.359(2) 4_556 ?
Tb1 O2 2.447(2) 2 ?
Tb1 O2 2.447(2) 3_456 ?
Tb1 N1 2.508(2) 4_556 ?
Tb1 N1 2.508(2) . ?
N1 C1 1.344(3) . ?
N1 C5 1.351(3) . ?
O1 C6 1.272(4) . ?
O2 C6 1.252(3) . ?
O2 Tb1 2.447(2) 2_554 ?
O3 C4 1.325(3) . ?
O3 H3D 1.1912 . ?
O4 H1W 0.8253 . ?
O4 H2W 0.8259 . ?
C1 C2 1.389(4) . ?
C1 C6 1.503(4) . ?
C2 C3 1.372(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.399(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.435(4) . ?
C5 C5 1.518(5) 4_556 ?



loop_

_geom_angle_atom_site_label_1

_geom_angle_atom_site_label_2

_geom_angle_atom_site_label_3

_geom_angle

_geom_angle_site_symmetry_1

_geom_angle_site_symmetry_3

_geom_angle_publ_flag























































O1 Tb1 O1 162.11(10) . 4_556 ?
O1 Tb1 O4 91.28(10) . . ?
O1 Tb1 O4 95.29(9) 4_556 . ?
O1 Tb1 O4 95.29(9) . 4_556 ?
O1 Tb1 O4 91.28(10) 4_556 4_556 ?
O4 Tb1 O4 136.77(10) . 4_556 ?
O1 Tb1 O2 81.34(8) . 2 ?
O1 Tb1 O2 84.42(8) 4_556 2 ?
O4 Tb1 O2 148.57(7) . 2 ?
O4 Tb1 O2 74.55(7) 4_556 2 ?
O1 Tb1 O2 84.42(8) . 3_456 ?
O1 Tb1 O2 81.34(8) 4_556 3_456 ?
O4 Tb1 O2 74.55(7) . 3_456 ?
O4 Tb1 O2 148.57(7) 4_556 3_456 ?
O2 Tb1 O2 74.35(9) 2 3_456 ?
O1 Tb1 N1 130.74(7) . 4_556 ?
O1 Tb1 N1 67.15(7) 4_556 4_556 ?
O4 Tb1 N1 72.75(8) . 4_556 ?
O4 Tb1 N1 70.75(7) 4_556 4_556 ?
O2 Tb1 N1 133.86(7) 2 4_556 ?
O2 Tb1 N1 131.43(7) 3_456 4_556 ?
O1 Tb1 N1 67.15(7) . . ?
O1 Tb1 N1 130.74(7) 4_556 . ?
O4 Tb1 N1 70.75(7) . . ?
O4 Tb1 N1 72.75(8) 4_556 . ?
O2 Tb1 N1 131.43(7) 2 . ?
O2 Tb1 N1 133.86(7) 3_456 . ?
N1 Tb1 N1 63.59(10) 4_556 . ?
C1 N1 C5 121.6(2) . . ?
C1 N1 Tb1 114.77(16) . . ?
C5 N1 Tb1 123.63(17) . . ?
C6 O1 Tb1 125.48(18) . . ?
C6 O2 Tb1 137.72(18) . 2_554 ?
C4 O3 H3D 111.6 . . ?
Tb1 O4 H1W 127.2 . . ?
Tb1 O4 H2W 116.2 . . ?
H1W O4 H2W 112.3 . . ?
N1 C1 C2 122.1(3) . . ?
N1 C1 C6 116.2(2) . . ?
C2 C1 C6 121.7(3) . . ?
C3 C2 C1 118.1(3) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
C2 C3 C4 121.1(3) . . ?
C2 C3 H3A 119.5 . . ?
C4 C3 H3A 119.5 . . ?
O3 C4 C3 117.1(2) . . ?
O3 C4 C5 124.6(3) . . ?
C3 C4 C5 118.3(2) . . ?
N1 C5 C4 118.8(2) . . ?
N1 C5 C5 114.57(15) . 4_556 ?
C4 C5 C5 126.64(16) . 4_556 ?
O2 C6 O1 124.0(3) . . ?
O2 C6 C1 120.0(3) . . ?
O1 C6 C1 116.0(2) . . ?



loop_

_geom_torsion_atom_site_label_1

_geom_torsion_atom_site_label_2

_geom_torsion_atom_site_label_3

_geom_torsion_atom_site_label_4

_geom_torsion

_geom_torsion_site_symmetry_1

_geom_torsion_site_symmetry_2

_geom_torsion_site_symmetry_3

_geom_torsion_site_symmetry_4

_geom_torsion_publ_flag














































O1 Tb1 N1 C1 -1.07(18) . . . . ?
O1 Tb1 N1 C1 178.99(18) 4_556 . . . ?
O4 Tb1 N1 C1 98.9(2) . . . . ?
O4 Tb1 N1 C1 -104.69(19) 4_556 . . . ?
O2 Tb1 N1 C1 -54.9(2) 2 . . . ?
O2 Tb1 N1 C1 55.5(2) 3_456 . . . ?
N1 Tb1 N1 C1 178.7(2) 4_556 . . . ?
O1 Tb1 N1 C5 179.9(2) . . . . ?
O1 Tb1 N1 C5 0.0(2) 4_556 . . . ?
O4 Tb1 N1 C5 -80.1(2) . . . . ?
O4 Tb1 N1 C5 76.3(2) 4_556 . . . ?
O2 Tb1 N1 C5 126.1(2) 2 . . . ?
O2 Tb1 N1 C5 -123.5(2) 3_456 . . . ?
N1 Tb1 N1 C5 -0.35(15) 4_556 . . . ?
O1 Tb1 O1 C6 -175.2(3) 4_556 . . . ?
O4 Tb1 O1 C6 -63.5(3) . . . . ?
O4 Tb1 O1 C6 73.7(3) 4_556 . . . ?
O2 Tb1 O1 C6 147.1(3) 2 . . . ?
O2 Tb1 O1 C6 -137.9(3) 3_456 . . . ?
N1 Tb1 O1 C6 4.6(3) 4_556 . . . ?
N1 Tb1 O1 C6 4.9(2) . . . . ?
C5 N1 C1 C2 -1.5(4) . . . . ?
Tb1 N1 C1 C2 179.4(2) . . . . ?
C5 N1 C1 C6 177.2(3) . . . . ?
Tb1 N1 C1 C6 -1.9(3) . . . . ?
N1 C1 C2 C3 0.2(4) . . . . ?
C6 C1 C2 C3 -178.4(3) . . . . ?
C1 C2 C3 C4 1.4(4) . . . . ?
C2 C3 C4 O3 177.4(3) . . . . ?
C2 C3 C4 C5 -1.7(4) . . . . ?
C1 N1 C5 C4 1.2(4) . . . . ?
Tb1 N1 C5 C4 -179.84(18) . . . . ?
C1 N1 C5 C5 -178.1(3) . . . 4_556 ?
Tb1 N1 C5 C5 0.9(4) . . . 4_556 ?
O3 C4 C5 N1 -178.7(3) . . . . ?
C3 C4 C5 N1 0.4(4) . . . . ?
O3 C4 C5 C5 0.5(5) . . . 4_556 ?
C3 C4 C5 C5 179.6(3) . . . 4_556 ?
Tb1 O2 C6 O1 -2.1(5) 2_554 . . . ?
Tb1 O2 C6 C1 177.37(19) 2_554 . . . ?
Tb1 O1 C6 O2 171.9(2) . . . . ?
Tb1 O1 C6 C1 -7.6(4) . . . . ?
N1 C1 C6 O2 -173.7(3) . . . . ?
C2 C1 C6 O2 5.0(5) . . . . ?
N1 C1 C6 O1 5.8(4) . . . . ?
C2 C1 C6 O1 -175.5(3) . . . . ?



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


O4 H1W O3 0.83 1.89 2.711(3) 176.1 5_556
O4 H2W O1 0.83 1.81 2.589(3) 157.8 3_456



_diffrn_measured_fraction_theta_max 0.999

_diffrn_reflns_theta_full        25.49

_diffrn_measured_fraction_theta_full 0.999

_refine_diff_density_max         0.349

_refine_diff_density_min         -0.775

_refine_diff_density_rms         0.078

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

data_7
_database_code_depnum_ccdc_archive 'CCDC 975875'
_audit_update_record             
;
2013-12-09 deposited with the CCDC.
2014-11-28 downloaded from the CCDC.
;



_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;

 ?

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         ?

_chemical_formula_sum            
'C12 H9 Dy N2 O8'

_chemical_formula_weight         471.71



loop_

_atom_type_symbol

_atom_type_description

_atom_type_scat_dispersion_real

_atom_type_scat_dispersion_imag

_atom_type_scat_source










C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
Dy Dy -0.1892 4.4098 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'



_symmetry_cell_setting           Orthorhombic

_symmetry_space_group_name_H-M   Pbcn



loop_

_symmetry_equiv_pos_as_xyz








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



_cell_length_a                   8.439(2)

_cell_length_b                   20.933(5)

_cell_length_c                   8.016(2)

_cell_angle_alpha                90.00

_cell_angle_beta                 90.00

_cell_angle_gamma                90.00

_cell_volume                     1416.0(6)

_cell_formula_units_Z            4

_cell_measurement_temperature    296(2)

_cell_measurement_reflns_used    3246

_cell_measurement_theta_min      2.60

_cell_measurement_theta_max      28.10



_exptl_crystal_description       block

_exptl_crystal_colour            yellow

_exptl_crystal_size_max          0.21

_exptl_crystal_size_mid          0.18

_exptl_crystal_size_min          0.15

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    2.213

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             900

_exptl_absorpt_coefficient_mu    5.323

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.4011

_exptl_absorpt_correction_T_max  0.5023

_exptl_absorpt_process_details   sadabs



_exptl_special_details           
;

 ?

;



_diffrn_ambient_temperature      296(2)

_diffrn_radiation_wavelength     0.71073

_diffrn_radiation_type           MoK\a

_diffrn_radiation_source         'fine-focus sealed tube'

_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'CCD area detector'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean ?

_diffrn_standards_number         0

_diffrn_standards_interval_count 0

_diffrn_standards_interval_time  0

_diffrn_standards_decay_%        0

_diffrn_reflns_number            9575

_diffrn_reflns_av_R_equivalents  0.0387

_diffrn_reflns_av_sigmaI/netI    0.0237

_diffrn_reflns_limit_h_min       -10

_diffrn_reflns_limit_h_max       10

_diffrn_reflns_limit_k_min       -25

_diffrn_reflns_limit_k_max       25

_diffrn_reflns_limit_l_min       -9

_diffrn_reflns_limit_l_max       9

_diffrn_reflns_theta_min         2.60

_diffrn_reflns_theta_max         25.49

_reflns_number_total             1314

_reflns_number_gt                1010

_reflns_threshold_expression     >2sigma(I)



_computing_data_collection       'Bruker SMART'

_computing_cell_refinement       'Bruker SMART'

_computing_data_reduction        'Bruker SAINT'

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_computing_molecular_graphics    'Bruker SHELXTL'

_computing_publication_material  'Bruker SHELXTL'



_refine_special_details          
;

 Refinement of F² against ALL reflections.  The weighted R-factor wR and

 goodness of fit S are based on F², conventional R-factors R are based

 on F, with F set to zero for negative F². The threshold expression of

 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is

 not relevant to the choice of reflections for refinement.  R-factors based

 on F² are statistically about twice as large as those based on F, and R-

 factors based on ALL data will be even larger.

;



_refine_ls_structure_factor_coef Fsqd

_refine_ls_matrix_type           full

_refine_ls_weighting_scheme      calc

_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0135P)²+2.5894P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_primary     direct

_atom_sites_solution_secondary   difmap

_atom_sites_solution_hydrogens   geom

_refine_ls_hydrogen_treatment    constr

_refine_ls_extinction_method     none

_refine_ls_extinction_coef       ?

_refine_ls_number_reflns         1314

_refine_ls_number_parameters     105

_refine_ls_number_restraints     0

_refine_ls_R_factor_all          0.0275

_refine_ls_R_factor_gt           0.0179

_refine_ls_wR_factor_ref         0.0438

_refine_ls_wR_factor_gt          0.0395

_refine_ls_goodness_of_fit_ref   1.061

_refine_ls_restrained_S_all      1.061

_refine_ls_shift/su_max          0.000

_refine_ls_shift/su_mean         0.000



loop_

_atom_site_label

_atom_site_type_symbol

_atom_site_fract_x

_atom_site_fract_y

_atom_site_fract_z

_atom_site_U_iso_or_equiv

_atom_site_adp_type

_atom_site_occupancy

_atom_site_symmetry_multiplicity

_atom_site_calc_flag

_atom_site_refinement_flags

_atom_site_disorder_assembly

_atom_site_disorder_group

















Dy1 Dy 0.0000 0.210636(9) 0.2500 0.01501(8) Uani 1 2 d S . .
N1 N 0.1228(3) 0.10961(13) 0.3523(3) 0.0167(6) Uani 1 1 d . . .
O1 O 0.2069(4) 0.22820(12) 0.4251(4) 0.0370(8) Uani 1 1 d . . .
O2 O 0.3860(3) 0.19668(12) 0.6120(3) 0.0275(6) Uani 1 1 d . . .
O3 O 0.1099(3) -0.06378(11) 0.3434(3) 0.0268(6) Uani 1 1 d . . .
H3D H 0.0000 -0.0665 0.2500 0.040 Uiso 1 2 d SR . .
O4 O -0.1548(4) 0.16972(13) 0.4683(4) 0.0426(8) Uani 1 1 d . . .
H1W H -0.1291 0.1388 0.5177 0.064 Uiso 1 1 d R . .
H2W H -0.2146 0.1942 0.5205 0.064 Uiso 1 1 d R . .
C1 C 0.2433(4) 0.11754(16) 0.4586(4) 0.0196(8) Uani 1 1 d . . .
C2 C 0.3249(5) 0.06631(18) 0.5257(5) 0.0245(8) Uani 1 1 d . . .
H2 H 0.4085 0.0727 0.5995 0.029 Uiso 1 1 calc R . .
C3 C 0.2795(4) 0.00603(17) 0.4809(4) 0.0229(8) Uani 1 1 d . . .
H3A H 0.3354 -0.0289 0.5218 0.027 Uiso 1 1 calc R . .
C4 C 0.1501(4) -0.00400(16) 0.3743(4) 0.0197(8) Uani 1 1 d . . .
C5 C 0.0703(4) 0.05094(16) 0.3080(4) 0.0149(7) Uani 1 1 d . . .
C6 C 0.2837(4) 0.18540(17) 0.5043(5) 0.0233(9) Uani 1 1 d . . .






_geom_special_details            
;

 All esds (except the esd in the dihedral angle between two l.s. planes)

 are estimated using the full covariance matrix.  The cell esds are taken

 into account individually in the estimation of esds in distances, angles

 and torsion angles; correlations between esds in cell parameters are only

 used when they are defined by crystal symmetry.  An approximate (isotropic)

 treatment of cell esds is used for estimating esds involving l.s. planes.

;



loop_

_geom_bond_atom_site_label_1

_geom_bond_atom_site_label_2

_geom_bond_distance

_geom_bond_site_symmetry_2

_geom_bond_publ_flag

























Dy1 O1 2.270(3) . ?
Dy1 O1 2.270(3) 3 ?
Dy1 O4 2.345(3) 3 ?
Dy1 O4 2.345(3) . ?
Dy1 O2 2.432(3) 4_456 ?
Dy1 O2 2.432(3) 2_554 ?
Dy1 N1 2.494(3) 3 ?
Dy1 N1 2.494(3) . ?
N1 C1 1.337(4) . ?
N1 C5 1.353(4) . ?
O1 C6 1.275(5) . ?
O2 C6 1.243(4) . ?
O2 Dy1 2.432(3) 2 ?
O3 C4 1.320(4) . ?
O3 H3D 1.1936 . ?
O4 H1W 0.7902 . ?
O4 H2W 0.8324 . ?
C1 C2 1.384(5) . ?
C1 C6 1.506(5) . ?
C2 C3 1.367(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.403(5) . ?
C3 H3A 0.9300 . ?
C4 C5 1.435(5) . ?
C5 C5 1.507(7) 3 ?



loop_

_geom_angle_atom_site_label_1

_geom_angle_atom_site_label_2

_geom_angle_atom_site_label_3

_geom_angle

_geom_angle_site_symmetry_1

_geom_angle_site_symmetry_3

_geom_angle_publ_flag























































O1 Dy1 O1 161.36(13) . 3 ?
O1 Dy1 O4 95.28(12) . 3 ?
O1 Dy1 O4 91.51(12) 3 3 ?
O1 Dy1 O4 91.51(12) . . ?
O1 Dy1 O4 95.28(12) 3 . ?
O4 Dy1 O4 137.16(13) 3 . ?
O1 Dy1 O2 83.91(10) . 4_456 ?
O1 Dy1 O2 81.24(10) 3 4_456 ?
O4 Dy1 O2 148.33(9) 3 4_456 ?
O4 Dy1 O2 74.43(9) . 4_456 ?
O1 Dy1 O2 81.24(10) . 2_554 ?
O1 Dy1 O2 83.91(10) 3 2_554 ?
O4 Dy1 O2 74.43(9) 3 2_554 ?
O4 Dy1 O2 148.33(9) . 2_554 ?
O2 Dy1 O2 74.16(12) 4_456 2_554 ?
O1 Dy1 N1 131.32(9) . 3 ?
O1 Dy1 N1 67.32(9) 3 3 ?
O4 Dy1 N1 71.12(9) 3 3 ?
O4 Dy1 N1 72.79(10) . 3 ?
O2 Dy1 N1 131.43(9) 4_456 3 ?
O2 Dy1 N1 133.74(9) 2_554 3 ?
O1 Dy1 N1 67.32(9) . . ?
O1 Dy1 N1 131.32(9) 3 . ?
O4 Dy1 N1 72.79(10) 3 . ?
O4 Dy1 N1 71.12(9) . . ?
O2 Dy1 N1 133.74(9) 4_456 . ?
O2 Dy1 N1 131.43(9) 2_554 . ?
N1 Dy1 N1 64.00(13) 3 . ?
C1 N1 C5 121.9(3) . . ?
C1 N1 Dy1 114.9(2) . . ?
C5 N1 Dy1 123.2(2) . . ?
C6 O1 Dy1 125.8(2) . . ?
C6 O2 Dy1 137.9(2) . 2 ?
C4 O3 H3D 111.3 . . ?
Dy1 O4 H1W 121.4 . . ?
Dy1 O4 H2W 119.2 . . ?
H1W O4 H2W 114.8 . . ?
N1 C1 C2 122.0(3) . . ?
N1 C1 C6 116.4(3) . . ?
C2 C1 C6 121.6(3) . . ?
C3 C2 C1 118.3(3) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
C2 C3 C4 121.1(3) . . ?
C2 C3 H3A 119.4 . . ?
C4 C3 H3A 119.4 . . ?
O3 C4 C3 117.1(3) . . ?
O3 C4 C5 124.7(3) . . ?
C3 C4 C5 118.1(3) . . ?
N1 C5 C4 118.5(3) . . ?
N1 C5 C5 114.82(19) . 3 ?
C4 C5 C5 126.7(2) . 3 ?
O2 C6 O1 124.4(3) . . ?
O2 C6 C1 120.3(3) . . ?
O1 C6 C1 115.2(3) . . ?



loop_

_geom_torsion_atom_site_label_1

_geom_torsion_atom_site_label_2

_geom_torsion_atom_site_label_3

_geom_torsion_atom_site_label_4

_geom_torsion

_geom_torsion_site_symmetry_1

_geom_torsion_site_symmetry_2

_geom_torsion_site_symmetry_3

_geom_torsion_site_symmetry_4

_geom_torsion_publ_flag














































O1 Dy1 N1 C1 1.3(2) . . . . ?
O1 Dy1 N1 C1 -178.8(2) 3 . . . ?
O4 Dy1 N1 C1 104.8(3) 3 . . . ?
O4 Dy1 N1 C1 -98.7(3) . . . . ?
O2 Dy1 N1 C1 -54.7(3) 4_456 . . . ?
O2 Dy1 N1 C1 55.2(3) 2_554 . . . ?
N1 Dy1 N1 C1 -178.2(3) 3 . . . ?
O1 Dy1 N1 C5 179.7(3) . . . . ?
O1 Dy1 N1 C5 -0.4(3) 3 . . . ?
O4 Dy1 N1 C5 -76.8(3) 3 . . . ?
O4 Dy1 N1 C5 79.8(3) . . . . ?
O2 Dy1 N1 C5 123.7(2) 4_456 . . . ?
O2 Dy1 N1 C5 -126.4(2) 2_554 . . . ?
N1 Dy1 N1 C5 0.19(19) 3 . . . ?
O1 Dy1 O1 C6 175.0(3) 3 . . . ?
O4 Dy1 O1 C6 -74.1(3) 3 . . . ?
O4 Dy1 O1 C6 63.6(3) . . . . ?
O2 Dy1 O1 C6 137.8(3) 4_456 . . . ?
O2 Dy1 O1 C6 -147.4(3) 2_554 . . . ?
N1 Dy1 O1 C6 -4.6(4) 3 . . . ?
N1 Dy1 O1 C6 -5.2(3) . . . . ?
C5 N1 C1 C2 2.1(5) . . . . ?
Dy1 N1 C1 C2 -179.5(3) . . . . ?
C5 N1 C1 C6 -176.8(3) . . . . ?
Dy1 N1 C1 C6 1.7(4) . . . . ?
N1 C1 C2 C3 -0.1(6) . . . . ?
C6 C1 C2 C3 178.7(4) . . . . ?
C1 C2 C3 C4 -2.2(6) . . . . ?
C2 C3 C4 O3 -177.0(3) . . . . ?
C2 C3 C4 C5 2.4(5) . . . . ?
C1 N1 C5 C4 -1.7(5) . . . . ?
Dy1 N1 C5 C4 179.9(2) . . . . ?
C1 N1 C5 C5 177.8(4) . . . 3 ?
Dy1 N1 C5 C5 -0.5(5) . . . 3 ?
O3 C4 C5 N1 179.0(3) . . . . ?
C3 C4 C5 N1 -0.5(5) . . . . ?
O3 C4 C5 C5 -0.6(6) . . . 3 ?
C3 C4 C5 C5 -180.0(4) . . . 3 ?
Dy1 O2 C6 O1 3.1(6) 2 . . . ?
Dy1 O2 C6 C1 -177.2(2) 2 . . . ?
Dy1 O1 C6 O2 -172.5(3) . . . . ?
Dy1 O1 C6 C1 7.8(5) . . . . ?
N1 C1 C6 O2 174.5(3) . . . . ?
C2 C1 C6 O2 -4.4(6) . . . . ?
N1 C1 C6 O1 -5.8(5) . . . . ?
C2 C1 C6 O1 175.4(4) . . . . ?



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


O4 H2W O1 0.83 1.81 2.581(4) 153.7 4_456
O4 H1W O3 0.79 1.93 2.709(4) 168.2 5_556



_diffrn_measured_fraction_theta_max 0.999

_diffrn_reflns_theta_full        25.49

_diffrn_measured_fraction_theta_full 0.999

_refine_diff_density_max         0.591

_refine_diff_density_min         -0.507

_refine_diff_density_rms         0.097

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

data_8
_database_code_depnum_ccdc_archive 'CCDC 975876'
_audit_update_record             
;
2013-12-09 deposited with the CCDC.
2014-11-28 downloaded from the CCDC.
;



_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;

 ?

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         ?

_chemical_formula_sum            
'C12 H9 Ho N2 O8'

_chemical_formula_weight         474.14



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



_symmetry_cell_setting           Orthorhombic

_symmetry_space_group_name_H-M   Pbcn



loop_

_symmetry_equiv_pos_as_xyz








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



_cell_length_a                   8.446(4)

_cell_length_b                   21.009(10)

_cell_length_c                   8.016(4)

_cell_angle_alpha                90.00

_cell_angle_beta                 90.00

_cell_angle_gamma                90.00

_cell_volume                     1422.4(12)

_cell_formula_units_Z            4

_cell_measurement_temperature    296(2)

_cell_measurement_reflns_used    5505

_cell_measurement_theta_min      2.60

_cell_measurement_theta_max      28.10



_exptl_crystal_description       block

_exptl_crystal_colour            orange

_exptl_crystal_size_max          0.41

_exptl_crystal_size_mid          0.32

_exptl_crystal_size_min          0.25

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    2.214

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             904

_exptl_absorpt_coefficient_mu    5.608

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.2070

_exptl_absorpt_correction_T_max  0.3345

_exptl_absorpt_process_details   sadabs



_exptl_special_details           
;

 ?

;



_diffrn_ambient_temperature      296(2)

_diffrn_radiation_wavelength     0.71073

_diffrn_radiation_type           MoK\a

_diffrn_radiation_source         'fine-focus sealed tube'

_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'CCD area detector'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean ?

_diffrn_standards_number         0

_diffrn_standards_interval_count ?

_diffrn_standards_interval_time  ?

_diffrn_standards_decay_%        ?

_diffrn_reflns_number            8996

_diffrn_reflns_av_R_equivalents  0.0266

_diffrn_reflns_av_sigmaI/netI    0.0172

_diffrn_reflns_limit_h_min       -10

_diffrn_reflns_limit_h_max       10

_diffrn_reflns_limit_k_min       -25

_diffrn_reflns_limit_k_max       25

_diffrn_reflns_limit_l_min       -9

_diffrn_reflns_limit_l_max       9

_diffrn_reflns_theta_min         2.60

_diffrn_reflns_theta_max         25.49

_reflns_number_total             1323

_reflns_number_gt                1188

_reflns_threshold_expression     >2sigma(I)



_computing_data_collection       'Bruker SMART'

_computing_cell_refinement       'Bruker SMART'

_computing_data_reduction        'Bruker SAINT'

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_computing_molecular_graphics    'Bruker SHELXTL'

_computing_publication_material  'Bruker SHELXTL'



_refine_special_details          
;

 Refinement of F² against ALL reflections.  The weighted R-factor wR and

 goodness of fit S are based on F², conventional R-factors R are based

 on F, with F set to zero for negative F². The threshold expression of

 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is

 not relevant to the choice of reflections for refinement.  R-factors based

 on F² are statistically about twice as large as those based on F, and R-

 factors based on ALL data will be even larger.

;



_refine_ls_structure_factor_coef Fsqd

_refine_ls_matrix_type           full

_refine_ls_weighting_scheme      calc

_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0346P)²+1.5666P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_primary     direct

_atom_sites_solution_secondary   difmap

_atom_sites_solution_hydrogens   geom

_refine_ls_hydrogen_treatment    constr

_refine_ls_extinction_method     none

_refine_ls_extinction_coef       ?

_refine_ls_number_reflns         1323

_refine_ls_number_parameters     105

_refine_ls_number_restraints     0

_refine_ls_R_factor_all          0.0219

_refine_ls_R_factor_gt           0.0196

_refine_ls_wR_factor_ref         0.0555

_refine_ls_wR_factor_gt          0.0533

_refine_ls_goodness_of_fit_ref   1.041

_refine_ls_restrained_S_all      1.041

_refine_ls_shift/su_max          0.000

_refine_ls_shift/su_mean         0.000



loop_

_atom_site_label

_atom_site_type_symbol

_atom_site_fract_x

_atom_site_fract_y

_atom_site_fract_z

_atom_site_U_iso_or_equiv

_atom_site_adp_type

_atom_site_occupancy

_atom_site_symmetry_multiplicity

_atom_site_calc_flag

_atom_site_refinement_flags

_atom_site_disorder_assembly

_atom_site_disorder_group

















Ho1 Ho 0.5000 0.289663(8) 0.7500 0.01278(10) Uani 1 2 d S . .
O1 O 0.2935(3) 0.27143(10) 0.5748(3) 0.0338(6) Uani 1 1 d . . .
O2 O 0.1141(2) 0.30272(10) 0.3871(3) 0.0251(5) Uani 1 1 d . . .
O3 O 0.3906(2) 0.56357(9) 0.6562(3) 0.0250(5) Uani 1 1 d . . .
H3D H 0.5000 0.5703 0.7500 0.037 Uiso 1 2 d SR . .
O4 O 0.6548(3) 0.33062(10) 0.5326(3) 0.0391(6) Uani 1 1 d . . .
H2W H 0.6290 0.3607 0.4670 0.059 Uiso 1 1 d R . .
H1W H 0.7116 0.3010 0.4920 0.059 Uiso 1 1 d R . .
N1 N 0.3782(3) 0.39002(10) 0.6474(3) 0.0150(5) Uani 1 1 d . . .
C1 C 0.2557(3) 0.38189(13) 0.5409(3) 0.0174(6) Uani 1 1 d . . .
C2 C 0.1736(3) 0.43308(14) 0.4734(4) 0.0216(6) Uani 1 1 d . . .
H2 H 0.0896 0.4267 0.4003 0.026 Uiso 1 1 calc R . .
C3 C 0.2203(4) 0.49358(13) 0.5182(3) 0.0219(7) Uani 1 1 d . . .
H3W H 0.1653 0.5285 0.4765 0.026 Uiso 1 1 calc R . .
C4 C 0.3496(3) 0.50353(13) 0.6257(3) 0.0173(6) Uani 1 1 d . . .
C5 C 0.4294(3) 0.44884(12) 0.6918(3) 0.0143(5) Uani 1 1 d . . .
C6 C 0.2168(3) 0.31429(13) 0.4964(4) 0.0204(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

























Ho1 O1 2.271(2) . ?
Ho1 O1 2.271(2) 3_656 ?
Ho1 O4 2.343(2) 3_656 ?
Ho1 O4 2.343(2) . ?
Ho1 O2 2.430(2) 4_556 ?
Ho1 O2 2.430(2) 2 ?
Ho1 N1 2.486(2) 3_656 ?
Ho1 N1 2.486(2) . ?
O1 C6 1.275(4) . ?
O2 C6 1.257(3) . ?
O2 Ho1 2.430(2) 2_554 ?
O3 C4 1.331(3) . ?
O3 H3D 1.1994 . ?
O4 H2W 0.8501 . ?
O4 H1W 0.8501 . ?
N1 C1 1.352(4) . ?
N1 C5 1.357(3) . ?
C1 C2 1.389(4) . ?
C1 C6 1.501(4) . ?
C2 C3 1.378(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.407(4) . ?
C3 H3W 0.9300 . ?
C4 C5 1.434(4) . ?
C5 C5 1.514(6) 3_656 ?



loop_

_geom_angle_atom_site_label_1

_geom_angle_atom_site_label_2

_geom_angle_atom_site_label_3

_geom_angle

_geom_angle_site_symmetry_1

_geom_angle_site_symmetry_3

_geom_angle_publ_flag























































O1 Ho1 O1 160.58(11) . 3_656 ?
O1 Ho1 O4 95.36(10) . 3_656 ?
O1 Ho1 O4 91.75(10) 3_656 3_656 ?
O1 Ho1 O4 91.75(10) . . ?
O1 Ho1 O4 95.36(10) 3_656 . ?
O4 Ho1 O4 136.90(11) 3_656 . ?
O1 Ho1 O2 83.69(8) . 4_556 ?
O1 Ho1 O2 80.82(8) 3_656 4_556 ?
O4 Ho1 O2 148.35(7) 3_656 4_556 ?
O4 Ho1 O2 74.66(8) . 4_556 ?
O1 Ho1 O2 80.82(8) . 2 ?
O1 Ho1 O2 83.69(8) 3_656 2 ?
O4 Ho1 O2 74.66(8) 3_656 2 ?
O4 Ho1 O2 148.35(7) . 2 ?
O2 Ho1 O2 73.96(10) 4_556 2 ?
O1 Ho1 N1 131.71(7) . 3_656 ?
O1 Ho1 N1 67.71(8) 3_656 3_656 ?
O4 Ho1 N1 70.93(8) 3_656 3_656 ?
O4 Ho1 N1 72.76(8) . 3_656 ?
O2 Ho1 N1 131.53(8) 4_556 3_656 ?
O2 Ho1 N1 133.78(8) 2 3_656 ?
O1 Ho1 N1 67.71(8) . . ?
O1 Ho1 N1 131.71(7) 3_656 . ?
O4 Ho1 N1 72.76(8) 3_656 . ?
O4 Ho1 N1 70.93(8) . . ?
O2 Ho1 N1 133.78(8) 4_556 . ?
O2 Ho1 N1 131.53(8) 2 . ?
N1 Ho1 N1 64.00(11) 3_656 . ?
C6 O1 Ho1 125.17(18) . . ?
C6 O2 Ho1 138.04(18) . 2_554 ?
C4 O3 H3D 115.4 . . ?
Ho1 O4 H2W 126.1 . . ?
Ho1 O4 H1W 109.3 . . ?
H2W O4 H1W 116.9 . . ?
C1 N1 C5 121.7(2) . . ?
C1 N1 Ho1 114.74(17) . . ?
C5 N1 Ho1 123.60(18) . . ?
N1 C1 C2 122.0(3) . . ?
N1 C1 C6 115.9(2) . . ?
C2 C1 C6 122.1(3) . . ?
C3 C2 C1 118.0(3) . . ?
C3 C2 H2 121.0 . . ?
C1 C2 H2 121.0 . . ?
C2 C3 C4 121.2(3) . . ?
C2 C3 H3W 119.4 . . ?
C4 C3 H3W 119.4 . . ?
O3 C4 C3 117.1(2) . . ?
O3 C4 C5 124.7(2) . . ?
C3 C4 C5 118.2(2) . . ?
N1 C5 C4 118.9(2) . . ?
N1 C5 C5 114.40(15) . 3_656 ?
C4 C5 C5 126.75(16) . 3_656 ?
O2 C6 O1 123.9(3) . . ?
O2 C6 C1 120.0(2) . . ?
O1 C6 C1 116.1(2) . . ?



loop_

_geom_torsion_atom_site_label_1

_geom_torsion_atom_site_label_2

_geom_torsion_atom_site_label_3

_geom_torsion_atom_site_label_4

_geom_torsion

_geom_torsion_site_symmetry_1

_geom_torsion_site_symmetry_2

_geom_torsion_site_symmetry_3

_geom_torsion_site_symmetry_4

_geom_torsion_publ_flag














































O1 Ho1 O1 C6 -175.4(3) 3_656 . . . ?
O4 Ho1 O1 C6 73.6(3) 3_656 . . . ?
O4 Ho1 O1 C6 -63.8(3) . . . . ?
O2 Ho1 O1 C6 -138.2(3) 4_556 . . . ?
O2 Ho1 O1 C6 147.1(3) 2 . . . ?
N1 Ho1 O1 C6 4.4(3) 3_656 . . . ?
N1 Ho1 O1 C6 4.7(2) . . . . ?
O1 Ho1 N1 C1 -0.75(18) . . . . ?
O1 Ho1 N1 C1 179.30(17) 3_656 . . . ?
O4 Ho1 N1 C1 -104.22(19) 3_656 . . . ?
O4 Ho1 N1 C1 99.4(2) . . . . ?
O2 Ho1 N1 C1 55.4(2) 4_556 . . . ?
O2 Ho1 N1 C1 -54.4(2) 2 . . . ?
N1 Ho1 N1 C1 179.0(2) 3_656 . . . ?
O1 Ho1 N1 C5 179.8(2) . . . . ?
O1 Ho1 N1 C5 -0.1(2) 3_656 . . . ?
O4 Ho1 N1 C5 76.4(2) 3_656 . . . ?
O4 Ho1 N1 C5 -80.0(2) . . . . ?
O2 Ho1 N1 C5 -124.05(19) 4_556 . . . ?
O2 Ho1 N1 C5 126.2(2) 2 . . . ?
N1 Ho1 N1 C5 -0.39(15) 3_656 . . . ?
C5 N1 C1 C2 -1.2(4) . . . . ?
Ho1 N1 C1 C2 179.3(2) . . . . ?
C5 N1 C1 C6 177.1(2) . . . . ?
Ho1 N1 C1 C6 -2.3(3) . . . . ?
N1 C1 C2 C3 0.0(4) . . . . ?
C6 C1 C2 C3 -178.3(3) . . . . ?
C1 C2 C3 C4 1.5(4) . . . . ?
C2 C3 C4 O3 177.1(3) . . . . ?
C2 C3 C4 C5 -1.7(4) . . . . ?
C1 N1 C5 C4 1.0(4) . . . . ?
Ho1 N1 C5 C4 -179.64(17) . . . . ?
C1 N1 C5 C5 -178.4(3) . . . 3_656 ?
Ho1 N1 C5 C5 1.0(4) . . . 3_656 ?
O3 C4 C5 N1 -178.3(2) . . . . ?
C3 C4 C5 N1 0.5(4) . . . . ?
O3 C4 C5 C5 1.0(5) . . . 3_656 ?
C3 C4 C5 C5 179.7(3) . . . 3_656 ?
Ho1 O2 C6 O1 -2.2(5) 2_554 . . . ?
Ho1 O2 C6 C1 177.64(19) 2_554 . . . ?
Ho1 O1 C6 O2 172.3(2) . . . . ?
Ho1 O1 C6 C1 -7.6(4) . . . . ?
N1 C1 C6 O2 -173.7(2) . . . . ?
C2 C1 C6 O2 4.6(4) . . . . ?
N1 C1 C6 O1 6.1(4) . . . . ?
C2 C1 C6 O1 -175.5(3) . . . . ?



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


O4 H1W O1 0.85 1.76 2.591(3) 166.7 4_556
O4 H2W O3 0.85 1.88 2.717(3) 167.5 5_666



_diffrn_measured_fraction_theta_max 0.998

_diffrn_reflns_theta_full        25.49

_diffrn_measured_fraction_theta_full 0.998

_refine_diff_density_max         0.288

_refine_diff_density_min         -1.549

_refine_diff_density_rms         0.158

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

data_9
_database_code_depnum_ccdc_archive 'CCDC 975877'
_audit_update_record             
;
2013-12-09 deposited with the CCDC.
2014-11-28 downloaded from the CCDC.
;



_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;

 ?

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         ?

_chemical_formula_sum            
'C12 H9 Er N2 O8'

_chemical_formula_weight         476.47



loop_

_atom_type_symbol

_atom_type_description

_atom_type_scat_dispersion_real

_atom_type_scat_dispersion_imag

_atom_type_scat_source










C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Er Er -0.2586 4.9576 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'



_symmetry_cell_setting           Orthorhombic

_symmetry_space_group_name_H-M   Pbcn



loop_

_symmetry_equiv_pos_as_xyz








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



_cell_length_a                   8.4022(15)

_cell_length_b                   20.939(4)

_cell_length_c                   7.9883(14)

_cell_angle_alpha                90.00

_cell_angle_beta                 90.00

_cell_angle_gamma                90.00

_cell_volume                     1405.4(4)

_cell_formula_units_Z            4

_cell_measurement_temperature    293(2)

_cell_measurement_reflns_used    4440

_cell_measurement_theta_min      2.61

_cell_measurement_theta_max      28.15



_exptl_crystal_description       block

_exptl_crystal_colour            yellow

_exptl_crystal_size_max          0.21

_exptl_crystal_size_mid          0.15

_exptl_crystal_size_min          0.10

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    2.252

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             908

_exptl_absorpt_coefficient_mu    6.018

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.3647

_exptl_absorpt_correction_T_max  0.5844

_exptl_absorpt_process_details   sadabs



_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  'CCD area detector'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean ?

_diffrn_standards_number         0

_diffrn_standards_interval_count 0

_diffrn_standards_interval_time  0

_diffrn_standards_decay_%        0

_diffrn_reflns_number            9727

_diffrn_reflns_av_R_equivalents  0.0284

_diffrn_reflns_av_sigmaI/netI    0.0166

_diffrn_reflns_limit_h_min       -10

_diffrn_reflns_limit_h_max       10

_diffrn_reflns_limit_k_min       -25

_diffrn_reflns_limit_k_max       25

_diffrn_reflns_limit_l_min       -9

_diffrn_reflns_limit_l_max       9

_diffrn_reflns_theta_min         2.61

_diffrn_reflns_theta_max         25.47

_reflns_number_total             1304

_reflns_number_gt                1061

_reflns_threshold_expression     >2sigma(I)



_computing_data_collection       'Bruker SMART'

_computing_cell_refinement       'Bruker SMART'

_computing_data_reduction        'Bruker SAINT'

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_computing_molecular_graphics    'Bruker SHELXTL'

_computing_publication_material  'Bruker SHELXTL'



_refine_special_details          
;

 Refinement of F² against ALL reflections.  The weighted R-factor wR and

 goodness of fit S are based on F², conventional R-factors R are based

 on F, with F set to zero for negative F². The threshold expression of

 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is

 not relevant to the choice of reflections for refinement.  R-factors based

 on F² are statistically about twice as large as those based on F, and R-

 factors based on ALL data will be even larger.

;



_refine_ls_structure_factor_coef Fsqd

_refine_ls_matrix_type           full

_refine_ls_weighting_scheme      calc

_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0116P)²+2.4897P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_primary     direct

_atom_sites_solution_secondary   difmap

_atom_sites_solution_hydrogens   geom

_refine_ls_hydrogen_treatment    constr

_refine_ls_extinction_method     none

_refine_ls_extinction_coef       ?

_refine_ls_number_reflns         1304

_refine_ls_number_parameters     105

_refine_ls_number_restraints     0

_refine_ls_R_factor_all          0.0218

_refine_ls_R_factor_gt           0.0147

_refine_ls_wR_factor_ref         0.0349

_refine_ls_wR_factor_gt          0.0319

_refine_ls_goodness_of_fit_ref   1.046

_refine_ls_restrained_S_all      1.046

_refine_ls_shift/su_max          0.000

_refine_ls_shift/su_mean         0.000



loop_

_atom_site_label

_atom_site_type_symbol

_atom_site_fract_x

_atom_site_fract_y

_atom_site_fract_z

_atom_site_U_iso_or_equiv

_atom_site_adp_type

_atom_site_occupancy

_atom_site_symmetry_multiplicity

_atom_site_calc_flag

_atom_site_refinement_flags

_atom_site_disorder_assembly

_atom_site_disorder_group

















Er1 Er 0.0000 0.209972(8) 0.7500 0.01313(7) Uani 1 2 d S . .
N1 N 0.1224(3) 0.11009(11) 0.6478(3) 0.0146(5) Uani 1 1 d . . .
O1 O 0.2054(3) 0.22895(10) 0.5751(3) 0.0319(6) Uani 1 1 d . . .
O2 O 0.3862(3) 0.19781(10) 0.3871(3) 0.0241(5) Uani 1 1 d . . .
O3 O 0.1100(3) -0.06340(9) 0.6557(3) 0.0240(5) Uani 1 1 d . . .
H3D H 0.0000 -0.0662 0.7500 0.036 Uiso 1 2 d SR . .
O4 O -0.1546(3) 0.16965(11) 0.5334(3) 0.0378(7) Uani 1 1 d . . .
H1W H -0.1370 0.1372 0.4784 0.057 Uiso 1 1 d R . .
H2W H -0.2097 0.1955 0.4824 0.057 Uiso 1 1 d R . .
C1 C 0.2443(4) 0.11832(14) 0.5407(4) 0.0172(6) Uani 1 1 d . . .
C2 C 0.3265(4) 0.06719(15) 0.4730(4) 0.0216(7) Uani 1 1 d . . .
H2 H 0.4104 0.0737 0.3991 0.026 Uiso 1 1 calc R . .
C3 C 0.2809(4) 0.00690(15) 0.5177(4) 0.0220(7) Uani 1 1 d . . .
H3A H 0.3370 -0.0280 0.4760 0.026 Uiso 1 1 calc R . .
C4 C 0.1513(4) -0.00348(14) 0.6252(4) 0.0167(6) Uani 1 1 d . . .
C5 C 0.0705(4) 0.05115(13) 0.6918(4) 0.0136(6) Uani 1 1 d . . .
C6 C 0.2841(4) 0.18630(14) 0.4963(4) 0.0199(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

























Er1 O1 2.255(2) . ?
Er1 O1 2.255(2) 3_556 ?
Er1 O4 2.323(2) . ?
Er1 O4 2.323(2) 3_556 ?
Er1 O2 2.417(2) 2 ?
Er1 O2 2.417(2) 4_456 ?
Er1 N1 2.469(2) . ?
Er1 N1 2.469(2) 3_556 ?
N1 C1 1.346(4) . ?
N1 C5 1.355(4) . ?
O1 C6 1.277(4) . ?
O2 C6 1.247(4) . ?
O2 Er1 2.417(2) 2_554 ?
O3 C4 1.324(4) . ?
O3 H3D 1.1932 . ?
O4 H1W 0.8226 . ?
O4 H2W 0.8214 . ?
C1 C2 1.384(4) . ?
C1 C6 1.505(4) . ?
C2 C3 1.367(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.404(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.433(4) . ?
C5 C5 1.506(6) 3_556 ?



loop_

_geom_angle_atom_site_label_1

_geom_angle_atom_site_label_2

_geom_angle_atom_site_label_3

_geom_angle

_geom_angle_site_symmetry_1

_geom_angle_site_symmetry_3

_geom_angle_publ_flag























































O1 Er1 O1 159.70(11) . 3_556 ?
O1 Er1 O4 91.75(10) . . ?
O1 Er1 O4 95.60(10) 3_556 . ?
O1 Er1 O4 95.60(10) . 3_556 ?
O1 Er1 O4 91.75(10) 3_556 3_556 ?
O4 Er1 O4 137.37(11) . 3_556 ?
O1 Er1 O2 80.63(8) . 2 ?
O1 Er1 O2 83.18(8) 3_556 2 ?
O4 Er1 O2 148.12(8) . 2 ?
O4 Er1 O2 74.43(7) 3_556 2 ?
O1 Er1 O2 83.18(8) . 4_456 ?
O1 Er1 O2 80.63(8) 3_556 4_456 ?
O4 Er1 O2 74.43(7) . 4_456 ?
O4 Er1 O2 148.12(8) 3_556 4_456 ?
O2 Er1 O2 73.95(10) 2 4_456 ?
O1 Er1 N1 68.03(8) . . ?
O1 Er1 N1 132.27(8) 3_556 . ?
O4 Er1 N1 71.25(8) . . ?
O4 Er1 N1 72.89(8) 3_556 . ?
O2 Er1 N1 131.44(8) 2 . ?
O2 Er1 N1 133.74(8) 4_456 . ?
O1 Er1 N1 132.27(8) . 3_556 ?
O1 Er1 N1 68.03(8) 3_556 3_556 ?
O4 Er1 N1 72.89(8) . 3_556 ?
O4 Er1 N1 71.25(8) 3_556 3_556 ?
O2 Er1 N1 133.74(8) 2 3_556 ?
O2 Er1 N1 131.44(8) 4_456 3_556 ?
N1 Er1 N1 64.25(11) . 3_556 ?
C1 N1 C5 121.8(2) . . ?
C1 N1 Er1 114.76(18) . . ?
C5 N1 Er1 123.46(19) . . ?
C6 O1 Er1 125.34(19) . . ?
C6 O2 Er1 138.02(19) . 2_554 ?
C4 O3 H3D 111.4 . . ?
Er1 O4 H1W 126.7 . . ?
Er1 O4 H2W 116.4 . . ?
H1W O4 H2W 112.4 . . ?
N1 C1 C2 121.9(3) . . ?
N1 C1 C6 116.1(3) . . ?
C2 C1 C6 121.9(3) . . ?
C3 C2 C1 118.2(3) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
C2 C3 C4 121.3(3) . . ?
C2 C3 H3A 119.3 . . ?
C4 C3 H3A 119.3 . . ?
O3 C4 C3 117.5(3) . . ?
O3 C4 C5 124.3(3) . . ?
C3 C4 C5 118.1(3) . . ?
N1 C5 C4 118.6(3) . . ?
N1 C5 C5 114.41(16) . 3_556 ?
C4 C5 C5 127.01(17) . 3_556 ?
O2 C6 O1 124.5(3) . . ?
O2 C6 C1 120.0(3) . . ?
O1 C6 C1 115.5(3) . . ?



loop_

_geom_torsion_atom_site_label_1

_geom_torsion_atom_site_label_2

_geom_torsion_atom_site_label_3

_geom_torsion_atom_site_label_4

_geom_torsion

_geom_torsion_site_symmetry_1

_geom_torsion_site_symmetry_2

_geom_torsion_site_symmetry_3

_geom_torsion_site_symmetry_4

_geom_torsion_publ_flag














































O1 Er1 N1 C1 -1.0(2) . . . . ?
O1 Er1 N1 C1 179.18(19) 3_556 . . . ?
O4 Er1 N1 C1 98.9(2) . . . . ?
O4 Er1 N1 C1 -104.5(2) 3_556 . . . ?
O2 Er1 N1 C1 -54.8(2) 2 . . . ?
O2 Er1 N1 C1 54.8(2) 4_456 . . . ?
N1 Er1 N1 C1 178.5(3) 3_556 . . . ?
O1 Er1 N1 C5 -179.7(2) . . . . ?
O1 Er1 N1 C5 0.5(3) 3_556 . . . ?
O4 Er1 N1 C5 -79.8(2) . . . . ?
O4 Er1 N1 C5 76.8(2) 3_556 . . . ?
O2 Er1 N1 C5 126.5(2) 2 . . . ?
O2 Er1 N1 C5 -124.0(2) 4_456 . . . ?
N1 Er1 N1 C5 -0.22(16) 3_556 . . . ?
O1 Er1 O1 C6 -176.0(3) 3_556 . . . ?
O4 Er1 O1 C6 -64.6(3) . . . . ?
O4 Er1 O1 C6 73.3(3) 3_556 . . . ?
O2 Er1 O1 C6 146.5(3) 2 . . . ?
O2 Er1 O1 C6 -138.7(3) 4_456 . . . ?
N1 Er1 O1 C6 4.3(3) . . . . ?
N1 Er1 O1 C6 3.7(3) 3_556 . . . ?
C5 N1 C1 C2 -1.8(4) . . . . ?
Er1 N1 C1 C2 179.5(2) . . . . ?
C5 N1 C1 C6 177.1(3) . . . . ?
Er1 N1 C1 C6 -1.7(3) . . . . ?
N1 C1 C2 C3 -0.1(5) . . . . ?
C6 C1 C2 C3 -178.9(3) . . . . ?
C1 C2 C3 C4 2.0(5) . . . . ?
C2 C3 C4 O3 176.7(3) . . . . ?
C2 C3 C4 C5 -2.0(5) . . . . ?
C1 N1 C5 C4 1.7(4) . . . . ?
Er1 N1 C5 C4 -179.72(19) . . . . ?
C1 N1 C5 C5 -178.1(3) . . . 3_556 ?
Er1 N1 C5 C5 0.6(4) . . . 3_556 ?
O3 C4 C5 N1 -178.4(3) . . . . ?
C3 C4 C5 N1 0.2(4) . . . . ?
O3 C4 C5 C5 1.3(6) . . . 3_556 ?
C3 C4 C5 C5 179.9(3) . . . 3_556 ?
Er1 O2 C6 O1 -1.4(5) 2_554 . . . ?
Er1 O2 C6 C1 177.4(2) 2_554 . . . ?
Er1 O1 C6 O2 172.2(2) . . . . ?
Er1 O1 C6 C1 -6.7(4) . . . . ?
N1 C1 C6 O2 -173.8(3) . . . . ?
C2 C1 C6 O2 5.0(5) . . . . ?
N1 C1 C6 O1 5.1(4) . . . . ?
C2 C1 C6 O1 -176.0(3) . . . . ?



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



O3 H3D O3 1.19 1.19 2.384(4) 174.4 3_556
O4 H1W O3 0.82 1.89 2.715(3) 176.1 5_556
O4 H2W O1 0.82 1.79 2.577(3) 158.9 4_456



_diffrn_measured_fraction_theta_max 0.999

_diffrn_reflns_theta_full        25.47

_diffrn_measured_fraction_theta_full 0.999

_refine_diff_density_max         0.428

_refine_diff_density_min         -0.655

_refine_diff_density_rms         0.081

