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

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

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H15 N O11 Pr'
_chemical_formula_weight         454.13

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'
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   p21/c

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

_cell_length_a                   15.930(6)
_cell_length_b                   13.588(5)
_cell_length_c                   6.663(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.392(5)
_cell_angle_gamma                90.00
_cell_volume                     1430.2(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1581
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      23.31

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.109
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             892
_exptl_absorpt_coefficient_mu    3.465
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.541
_exptl_absorpt_correction_T_max  0.707
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6748
_diffrn_reflns_av_R_equivalents  0.0568
_diffrn_reflns_av_sigmaI/netI    0.0630
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         1.29
_diffrn_reflns_theta_max         24.62
_reflns_number_total             2393
_reflns_number_gt                1916
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL-XP (Bruker, 2004)'
_computing_publication_material  SHELXL-97

_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)+(0.0875P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2393
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0504
_refine_ls_wR_factor_ref         0.1435
_refine_ls_wR_factor_gt          0.1322
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.012
_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 0.74945(3) 0.94004(3) 1.02861(7) 0.0266(2) Uani 1 1 d . . .
C1 C 0.6433(5) 0.7839(6) 0.6575(12) 0.0274(19) Uani 1 1 d . . .
C2 C 0.5485(5) 0.7834(6) 0.6230(12) 0.0261(18) Uani 1 1 d . . .
C3 C 0.5056(5) 0.8738(6) 0.6211(12) 0.0277(18) Uani 1 1 d . . .
H3A H 0.5370 0.9312 0.6453 0.033 Uiso 1 1 calc R . .
C4 C 0.3768(5) 0.7975(6) 0.5552(13) 0.031(2) Uani 1 1 d . . .
H4A H 0.3181 0.8022 0.5309 0.037 Uiso 1 1 calc R . .
C5 C 0.4136(5) 0.7042(6) 0.5578(12) 0.0297(19) Uani 1 1 d . . .
C6 C 0.5007(5) 0.6972(6) 0.5930(12) 0.0273(18) Uani 1 1 d . . .
H6A H 0.5271 0.6361 0.5968 0.033 Uiso 1 1 calc R . .
C7 C 0.3577(5) 0.6144(6) 0.5218(13) 0.0292(19) Uani 1 1 d . . .
C8 C 0.8993(8) 0.9524(8) 1.3290(19) 0.059(3) Uani 1 1 d . . .
C9 C 0.9813(8) 0.9539(7) 1.489(2) 0.079(4) Uani 1 1 d . . .
H9A H 0.9665 0.9325 1.6188 0.095 Uiso 1 1 calc R . .
H9B H 1.0219 0.9073 1.4476 0.095 Uiso 1 1 calc R . .
N1 N 0.4216(4) 0.8805(5) 0.5860(10) 0.0295(16) Uani 1 1 d . . .
O1 O 0.6806(4) 0.8620(4) 0.7099(9) 0.0360(14) Uani 1 1 d . . .
O2 O 0.6796(4) 0.7044(4) 0.6333(11) 0.0446(17) Uani 1 1 d . . .
O3 O 0.2813(4) 0.6245(4) 0.4505(10) 0.0379(15) Uani 1 1 d . . .
O4 O 0.3898(4) 0.5309(4) 0.5630(10) 0.0415(16) Uani 1 1 d . . .
O5 O 0.8886(4) 1.0133(5) 1.1850(13) 0.063(2) Uani 1 1 d . . .
O6 O 0.8490(5) 0.8830(7) 1.3394(15) 0.085(3) Uani 1 1 d . . .
O1W O 0.6916(5) 0.9771(5) 1.3562(10) 0.057(2) Uani 1 1 d . . .
H1WA H 0.6981 0.9291 1.4311 0.068 Uiso 1 1 d R . .
H1WB H 0.6393 0.9908 1.3306 0.068 Uiso 1 1 d R . .
O2W O 0.8024(5) 1.0280(5) 0.7362(10) 0.0546(19) Uani 1 1 d . . .
H2WA H 0.8086 1.0867 0.7629 0.065 Uiso 1 1 d R . .
H2WB H 0.7667 1.0209 0.6309 0.065 Uiso 1 1 d R . .
O3W O 0.8557(5) 0.8170(6) 0.9244(16) 0.087(3) Uani 1 1 d . . .
H3WA H 0.8337 0.7624 0.9114 0.104 Uiso 1 1 d R . .
H3WB H 0.8714 0.8350 0.8129 0.104 Uiso 1 1 d R . .
O4W O 0.0290(4) 0.8378(6) -0.0065(17) 0.107(4) Uani 1 1 d G . .
H4WA H -0.0165 0.8176 -0.0748 0.128 Uiso 1 1 d R . .
H4WB H 0.0227 0.8485 0.1163 0.128 Uiso 1 1 d R . .
O5W O 0.8374(5) 0.2279(5) 0.6894(16) 0.091(3) Uani 1 1 d G . .
H5WA H 0.8536 0.2335 0.8154 0.109 Uiso 1 1 d R . .
H5WB H 0.8809 0.2378 0.6304 0.109 Uiso 1 1 d R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Pr1 O2 2.403(6) 4_576 ?
Pr1 O1 2.497(6) . ?
Pr1 O2W 2.522(7) . ?
Pr1 O1W 2.527(7) . ?
Pr1 O5 2.529(6) . ?
Pr1 O3W 2.538(7) . ?
Pr1 O4 2.544(6) 2_656 ?
Pr1 O6 2.561(8) . ?
Pr1 O3 2.561(6) 2_656 ?
Pr1 C7 2.914(8) 2_656 ?
C1 O1 1.245(9) . ?
C1 O2 1.246(10) . ?
C1 C2 1.497(11) . ?
C2 C6 1.397(10) . ?
C2 C3 1.406(10) . ?
C3 N1 1.331(10) . ?
C3 H3A 0.9300 . ?
C4 N1 1.336(10) . ?
C4 C5 1.396(11) . ?
C4 H4A 0.9300 . ?
C5 C6 1.381(11) . ?
C5 C7 1.511(11) . ?
C6 H6A 0.9300 . ?
C7 O3 1.256(9) . ?
C7 O4 1.260(10) . ?
C7 Pr1 2.914(8) 2_646 ?
C8 O6 1.244(13) . ?
C8 O5 1.262(14) . ?
C8 C9 1.576(16) . ?
C9 C9 1.39(2) 3_778 ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
O2 Pr1 2.403(6) 4_575 ?
O3 Pr1 2.561(6) 2_646 ?
O4 Pr1 2.544(6) 2_646 ?
O1W H1WA 0.8200 . ?
O1W H1WB 0.8500 . ?
O2W H2WA 0.8200 . ?
O2W H2WB 0.8499 . ?
O3W H3WA 0.8199 . ?
O3W H3WB 0.8502 . ?
O4W H4WA 0.8501 . ?
O4W H4WB 0.8500 . ?
O5W H5WA 0.8501 . ?
O5W H5WB 0.8500 . ?

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 Pr1 O1 74.4(2) 4_576 . ?
O2 Pr1 O2W 145.6(2) 4_576 . ?
O1 Pr1 O2W 72.4(2) . . ?
O2 Pr1 O1W 71.2(2) 4_576 . ?
O1 Pr1 O1W 130.5(2) . . ?
O2W Pr1 O1W 140.2(2) . . ?
O2 Pr1 O5 128.0(2) 4_576 . ?
O1 Pr1 O5 141.6(3) . . ?
O2W Pr1 O5 76.6(3) . . ?
O1W Pr1 O5 87.9(3) . . ?
O2 Pr1 O3W 83.8(3) 4_576 . ?
O1 Pr1 O3W 73.9(2) . . ?
O2W Pr1 O3W 78.5(3) . . ?
O1W Pr1 O3W 134.2(3) . . ?
O5 Pr1 O3W 78.0(3) . . ?
O2 Pr1 O4 92.5(2) 4_576 2_656 ?
O1 Pr1 O4 74.20(19) . 2_656 ?
O2W Pr1 O4 87.3(2) . 2_656 ?
O1W Pr1 O4 72.9(2) . 2_656 ?
O5 Pr1 O4 126.8(2) . 2_656 ?
O3W Pr1 O4 147.7(3) . 2_656 ?
O2 Pr1 O6 77.3(3) 4_576 . ?
O1 Pr1 O6 135.9(3) . . ?
O2W Pr1 O6 122.3(3) . . ?
O1W Pr1 O6 67.6(3) . . ?
O5 Pr1 O6 50.7(3) . . ?
O3W Pr1 O6 69.9(3) . . ?
O4 Pr1 O6 140.4(3) 2_656 . ?
O2 Pr1 O3 133.2(2) 4_576 2_656 ?
O1 Pr1 O3 113.29(19) . 2_656 ?
O2W Pr1 O3 70.3(2) . 2_656 ?
O1W Pr1 O3 70.4(2) . 2_656 ?
O5 Pr1 O3 75.9(2) . 2_656 ?
O3W Pr1 O3 143.0(3) . 2_656 ?
O4 Pr1 O3 51.04(19) 2_656 2_656 ?
O6 Pr1 O3 110.8(3) . 2_656 ?
O2 Pr1 C7 114.3(2) 4_576 2_656 ?
O1 Pr1 C7 93.5(2) . 2_656 ?
O2W Pr1 C7 77.0(2) . 2_656 ?
O1W Pr1 C7 70.4(2) . 2_656 ?
O5 Pr1 C7 101.3(2) . 2_656 ?
O3W Pr1 C7 154.8(3) . 2_656 ?
O4 Pr1 C7 25.6(2) 2_656 2_656 ?
O6 Pr1 C7 129.2(3) . 2_656 ?
O3 Pr1 C7 25.5(2) 2_656 2_656 ?
O1 C1 O2 124.3(8) . . ?
O1 C1 C2 118.8(7) . . ?
O2 C1 C2 116.9(7) . . ?
C6 C2 C3 118.3(7) . . ?
C6 C2 C1 123.1(7) . . ?
C3 C2 C1 118.5(7) . . ?
N1 C3 C2 122.6(7) . . ?
N1 C3 H3A 118.7 . . ?
C2 C3 H3A 118.7 . . ?
N1 C4 C5 123.4(8) . . ?
N1 C4 H4A 118.3 . . ?
C5 C4 H4A 118.3 . . ?
C6 C5 C4 118.4(7) . . ?
C6 C5 C7 122.1(7) . . ?
C4 C5 C7 119.6(8) . . ?
C5 C6 C2 119.0(7) . . ?
C5 C6 H6A 120.5 . . ?
C2 C6 H6A 120.5 . . ?
O3 C7 O4 121.9(7) . . ?
O3 C7 C5 119.6(7) . . ?
O4 C7 C5 118.5(8) . . ?
O3 C7 Pr1 61.4(4) . 2_646 ?
O4 C7 Pr1 60.6(4) . 2_646 ?
C5 C7 Pr1 177.5(6) . 2_646 ?
O6 C8 O5 121.0(10) . . ?
O6 C8 C9 117.1(11) . . ?
O5 C8 C9 121.6(11) . . ?
C9 C9 C8 113.0(14) 3_778 . ?
C9 C9 H9A 109.0 3_778 . ?
C8 C9 H9A 109.0 . . ?
C9 C9 H9B 109.0 3_778 . ?
C8 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C3 N1 C4 118.3(7) . . ?
C1 O1 Pr1 137.9(5) . . ?
C1 O2 Pr1 170.3(6) . 4_575 ?
C7 O3 Pr1 93.1(5) . 2_646 ?
C7 O4 Pr1 93.8(5) . 2_646 ?
C8 O5 Pr1 94.6(6) . . ?
C8 O6 Pr1 93.6(7) . . ?
Pr1 O1W H1WA 109.6 . . ?
Pr1 O1W H1WB 109.1 . . ?
H1WA O1W H1WB 109.8 . . ?
Pr1 O2W H2WA 109.6 . . ?
Pr1 O2W H2WB 109.2 . . ?
H2WA O2W H2WB 109.8 . . ?
Pr1 O3W H3WA 109.6 . . ?
Pr1 O3W H3WB 109.3 . . ?
H3WA O3W H3WB 109.8 . . ?
H4WA O4W H4WB 111.8 . . ?
H5WA O5W H5WB 106.2 . . ?

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 C1 C2 C6 -170.4(8) . . . . ?
O2 C1 C2 C6 8.9(12) . . . . ?
O1 C1 C2 C3 9.5(12) . . . . ?
O2 C1 C2 C3 -171.3(8) . . . . ?
C6 C2 C3 N1 -2.1(12) . . . . ?
C1 C2 C3 N1 178.1(7) . . . . ?
N1 C4 C5 C6 -0.3(13) . . . . ?
N1 C4 C5 C7 179.9(8) . . . . ?
C4 C5 C6 C2 -0.5(12) . . . . ?
C7 C5 C6 C2 179.3(7) . . . . ?
C3 C2 C6 C5 1.6(12) . . . . ?
C1 C2 C6 C5 -178.5(7) . . . . ?
C6 C5 C7 O3 -165.5(8) . . . . ?
C4 C5 C7 O3 14.3(12) . . . . ?
C6 C5 C7 O4 13.7(12) . . . . ?
C4 C5 C7 O4 -166.4(8) . . . . ?
C6 C5 C7 Pr1 82(14) . . . 2_646 ?
C4 C5 C7 Pr1 -98(14) . . . 2_646 ?
O6 C8 C9 C9 -160.1(18) . . . 3_778 ?
O5 C8 C9 C9 26(2) . . . 3_778 ?
C2 C3 N1 C4 1.3(12) . . . . ?
C5 C4 N1 C3 -0.1(12) . . . . ?
O2 C1 O1 Pr1 -79.6(12) . . . . ?
C2 C1 O1 Pr1 99.6(9) . . . . ?
O2 Pr1 O1 C1 -8.8(8) 4_576 . . . ?
O2W Pr1 O1 C1 161.8(9) . . . . ?
O1W Pr1 O1 C1 -56.1(9) . . . . ?
O5 Pr1 O1 C1 123.8(8) . . . . ?
O3W Pr1 O1 C1 79.1(9) . . . . ?
O4 Pr1 O1 C1 -106.1(8) 2_656 . . . ?
O6 Pr1 O1 C1 43.2(9) . . . . ?
O3 Pr1 O1 C1 -139.6(8) 2_656 . . . ?
C7 Pr1 O1 C1 -123.1(8) 2_656 . . . ?
O1 C1 O2 Pr1 -90(3) . . . 4_575 ?
C2 C1 O2 Pr1 91(4) . . . 4_575 ?
O4 C7 O3 Pr1 3.4(9) . . . 2_646 ?
C5 C7 O3 Pr1 -177.4(7) . . . 2_646 ?
O3 C7 O4 Pr1 -3.4(9) . . . 2_646 ?
C5 C7 O4 Pr1 177.4(6) . . . 2_646 ?
O6 C8 O5 Pr1 4.0(13) . . . . ?
C9 C8 O5 Pr1 177.4(11) . . . . ?
O2 Pr1 O5 C8 -3.8(8) 4_576 . . . ?
O1 Pr1 O5 C8 -119.6(7) . . . . ?
O2W Pr1 O5 C8 -156.7(8) . . . . ?
O1W Pr1 O5 C8 60.3(7) . . . . ?
O3W Pr1 O5 C8 -75.9(7) . . . . ?
O4 Pr1 O5 C8 127.1(7) 2_656 . . . ?
O6 Pr1 O5 C8 -2.2(7) . . . . ?
O3 Pr1 O5 C8 130.6(8) 2_656 . . . ?
C7 Pr1 O5 C8 129.8(7) 2_656 . . . ?
O5 C8 O6 Pr1 -3.9(13) . . . . ?
C9 C8 O6 Pr1 -177.6(10) . . . . ?
O2 Pr1 O6 C8 -179.1(9) 4_576 . . . ?
O1 Pr1 O6 C8 129.8(8) . . . . ?
O2W Pr1 O6 C8 31.8(10) . . . . ?
O1W Pr1 O6 C8 -104.4(9) . . . . ?
O5 Pr1 O6 C8 2.2(7) . . . . ?
O3W Pr1 O6 C8 92.9(9) . . . . ?
O4 Pr1 O6 C8 -100.8(8) 2_656 . . . ?
O3 Pr1 O6 C8 -47.5(9) 2_656 . . . ?
C7 Pr1 O6 C8 -68.0(9) 2_656 . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        24.62
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         1.990
_refine_diff_density_min         -1.844
_refine_diff_density_rms         0.216
_database_code_depnum_ccdc_archive 'CCDC 967478'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
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#  from this site to visualise CIF-encoded structures and 
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data_CCDC
_audit_creation_date             2014-03-19
_audit_creation_method           
;
  Olex2 1.2
  (compiled Dec  5 2012 16:20:19, GUI svn.r4385)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C9 H11 Eu N O9, 2(H2 O)'
_chemical_formula_sum            'C9 H15 Eu N O11'
_chemical_formula_weight         465.18
_chemical_melting_point          ?
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   15.9131(14)
_cell_length_b                   13.5396(11)
_cell_length_c                   6.6475(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.6620(10)
_cell_angle_gamma                90.00
_cell_volume                     1419.5(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2419
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.06
_cell_measurement_theta_min      2.58
_exptl_absorpt_coefficient_mu    4.478
_exptl_absorpt_correction_T_max  0.475
_exptl_absorpt_correction_T_min  0.414
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.177
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             908
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            7176
_diffrn_reflns_theta_full        25.20
_diffrn_reflns_theta_max         25.20
_diffrn_reflns_theta_min         1.98
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_reflns_number_gt                2152
_reflns_number_total             2533
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'SHELXTL-XP (Bruker, 2004)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_refine_diff_density_max         0.763
_refine_diff_density_min         -0.716
_refine_diff_density_rms         0.139
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2533
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0310
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0427P)²+3.2957P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0764
_refine_ls_wR_factor_ref         0.0812
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  H6 of C6, {H9A,H9B} of C9, {H1WA,H1WB} of O1W, {H2WA,H2WB} of O2W, {H3WA,
  H3WB} of O3W, {H4WA,H4WB} of O4W, H3 of C3, H4 of C4, {H5WA,H5WB} of O5W
2.a Riding coordinates:
 O1W(H1WA,H1WB), O2W(H2WA,H2WB), O3W(H3WA,H3WB), O4W(H4WA,H4WB), O5W(H5WA,H5WB)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.250875(17) 1.06030(2) 0.46874(4) 0.02120(12) Uani 1 1 d . . .
C1 C 0.3582(3) 0.8868(4) 0.5200(8) 0.0197(12) Uani 1 1 d . . .
C2 C 0.4134(3) 0.7962(4) 0.5551(7) 0.0168(11) Uani 1 1 d . . .
C3 C 0.3767(3) 0.7028(4) 0.5520(8) 0.0209(12) Uani 1 1 d . . .
H3 H 0.3179 0.6986 0.5250 0.025 Uiso 1 1 calc R . .
C4 C 0.5049(3) 0.6265(4) 0.6200(7) 0.0186(11) Uani 1 1 d . . .
H4 H 0.5364 0.5688 0.6431 0.022 Uiso 1 1 calc R . .
C5 C 0.5482(3) 0.7157(4) 0.6235(7) 0.0169(11) Uani 1 1 d . . .
C6 C 0.5010(3) 0.8027(4) 0.5924(7) 0.0179(11) Uani 1 1 d . . .
H6 H 0.5278 0.8638 0.5968 0.022 Uiso 1 1 calc R . .
C7 C 0.6438(3) 0.7171(4) 0.6605(7) 0.0185(11) Uani 1 1 d . . .
C8 C 0.1009(4) 1.0496(5) 0.1700(11) 0.0396(17) Uani 1 1 d . . .
C9 C 0.0214(5) 1.0476(5) 0.0122(14) 0.057(2) Uani 1 1 d . . .
H9A H -0.0184 1.0962 0.0504 0.069 Uiso 1 1 calc R . .
H9B H 0.0371 1.0674 -0.1179 0.069 Uiso 1 1 calc R . .
N1 N 0.4204(3) 0.6189(3) 0.5853(7) 0.0208(10) Uani 1 1 d . . .
O1 O 0.3891(3) 0.9699(3) 0.5617(6) 0.0277(9) Uani 1 1 d . . .
O2 O 0.2817(2) 0.8758(3) 0.4481(6) 0.0280(9) Uani 1 1 d . . .
O3 O 0.6807(2) 0.6373(3) 0.7114(6) 0.0238(9) Uani 1 1 d . . .
O4 O 0.6798(3) 0.7964(3) 0.6325(7) 0.0331(10) Uani 1 1 d . . .
O5 O 0.1128(3) 0.9880(3) 0.3095(8) 0.0443(12) Uani 1 1 d . . .
O6 O 0.1516(3) 1.1184(4) 0.1565(9) 0.0654(17) Uani 1 1 d . . .
O1W O 0.1994(3) 0.9707(3) 0.7597(6) 0.0414(12) Uani 1 1 d . . .
H1WA H 0.1525 0.9955 0.7823 0.050 Uiso 1 1 d R . .
H1WB H 0.2350 0.9778 0.8658 0.050 Uiso 1 1 d R . .
O2W O 0.3073(3) 1.0236(3) 0.1415(6) 0.0412(12) Uani 1 1 d . . .
H2WA H 0.3596 1.0089 0.1667 0.049 Uiso 1 1 d R . .
H2WB H 0.3014 1.0722 0.0675 0.049 Uiso 1 1 d R . .
O3W O 0.1469(3) 1.1816(4) 0.5778(10) 0.0694(18) Uani 1 1 d . . .
H3WA H 0.1330 1.1636 0.6914 0.083 Uiso 1 1 d R . .
H3WB H 0.1024 1.1826 0.4915 0.083 Uiso 1 1 d R . .
O4W O 0.1621(4) 0.7726(4) 0.8008(10) 0.080(2) Uani 1 1 d . . .
H4WA H 0.2037 0.7342 0.8354 0.096 Uiso 1 1 d R . .
H4WB H 0.1190 0.7491 0.8471 0.096 Uiso 1 1 d R . .
O5W O -0.0278(4) 1.1639(5) 0.5083(11) 0.091(2) Uani 1 1 d . . .
H5WA H -0.0563 1.1742 0.3927 0.109 Uiso 1 1 d R . .
H5WB H -0.0246 1.1020 0.5294 0.109 Uiso 1 1 d R . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Eu1 C1 2.898(5) . ?
Eu1 C8 2.898(6) . ?
Eu1 O1 2.522(4) . ?
Eu1 O2 2.552(4) . ?
Eu1 O3 2.485(4) 2_656 ?
Eu1 O4 2.373(4) 3_676 ?
Eu1 O5 2.508(4) . ?
Eu1 O6 2.559(5) . ?
Eu1 O1W 2.511(4) . ?
Eu1 O2W 2.512(4) . ?
Eu1 O3W 2.507(5) . ?
C1 C2 1.508(7) . ?
C1 O1 1.245(6) . ?
C1 O2 1.255(6) . ?
C2 C3 1.392(7) . ?
C2 C6 1.385(7) . ?
C3 H3 0.9300 . ?
C3 N1 1.335(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.390(7) . ?
C4 N1 1.338(7) . ?
C5 C6 1.397(7) . ?
C5 C7 1.507(7) . ?
C6 H6 0.9300 . ?
C7 O3 1.256(6) . ?
C7 O4 1.243(6) . ?
C8 C9 1.532(9) . ?
C8 O5 1.243(8) . ?
C8 O6 1.245(8) . ?
C9 C9 1.456(13) 3_575 ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
O3 Eu1 2.485(3) 2_646 ?
O4 Eu1 2.373(4) 3_676 ?
O1W H1WA 0.8500 . ?
O1W H1WB 0.8500 . ?
O2W H2WA 0.8502 . ?
O2W H2WB 0.8201 . ?
O3W H3WA 0.8500 . ?
O3W H3WB 0.8499 . ?
O4W H4WA 0.8500 . ?
O4W H4WB 0.8499 . ?
O5W H5WA 0.8499 . ?
O5W H5WB 0.8501 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 Eu1 C1 117.29(17) . . ?
O1 Eu1 C1 25.35(13) . . ?
O1 Eu1 C8 139.07(16) . . ?
O1 Eu1 O2 50.97(12) . . ?
O1 Eu1 O6 140.55(18) . . ?
O2 Eu1 C1 25.64(13) . . ?
O2 Eu1 C8 93.49(16) . . ?
O2 Eu1 O6 111.09(16) . . ?
O3 Eu1 C1 93.18(13) 2_656 . ?
O3 Eu1 C8 146.52(17) 2_656 . ?
O3 Eu1 O1 74.08(12) 2_656 . ?
O3 Eu1 O2 113.01(12) 2_656 . ?
O3 Eu1 O5 141.65(16) 2_656 . ?
O3 Eu1 O6 135.85(17) 2_656 . ?
O3 Eu1 O1W 72.20(13) 2_656 . ?
O3 Eu1 O2W 131.14(15) 2_656 . ?
O3 Eu1 O3W 73.05(15) 2_656 . ?
O4 Eu1 C1 114.03(15) 3_676 . ?
O4 Eu1 C8 102.61(18) 3_676 . ?
O4 Eu1 O1 92.47(13) 3_676 . ?
O4 Eu1 O2 133.20(14) 3_676 . ?
O4 Eu1 O3 74.50(14) 3_676 2_656 ?
O4 Eu1 O5 127.86(15) 3_676 . ?
O4 Eu1 O6 77.21(15) 3_676 . ?
O4 Eu1 O1W 145.61(15) 3_676 . ?
O4 Eu1 O2W 71.51(15) 3_676 . ?
O4 Eu1 O3W 84.04(17) 3_676 . ?
O5 Eu1 C1 101.68(15) . . ?
O5 Eu1 C8 25.27(17) . . ?
O5 Eu1 O1 126.91(14) . . ?
O5 Eu1 O2 76.07(14) . . ?
O5 Eu1 O6 50.67(16) . . ?
O5 Eu1 O1W 77.22(16) . . ?
O5 Eu1 O2W 87.21(17) . . ?
O6 Eu1 C1 129.43(18) . . ?
O6 Eu1 C8 25.40(18) . . ?
O1W Eu1 C1 76.44(15) . . ?
O1W Eu1 C8 100.35(19) . . ?
O1W Eu1 O1 86.59(15) . . ?
O1W Eu1 O2 69.73(14) . . ?
O1W Eu1 O6 122.92(17) . . ?
O1W Eu1 O2W 139.68(14) . . ?
O2W Eu1 C1 70.60(14) . . ?
O2W Eu1 C8 75.74(19) . . ?
O2W Eu1 O1 73.44(14) . . ?
O2W Eu1 O2 70.49(13) . . ?
O2W Eu1 O6 67.16(18) . . ?
O3W Eu1 C1 154.01(19) . . ?
O3W Eu1 C8 73.48(19) . . ?
O3W Eu1 O1 146.67(16) . . ?
O3W Eu1 O2 142.74(16) . . ?
O3W Eu1 O5 78.63(16) . . ?
O3W Eu1 O6 70.9(2) . . ?
O3W Eu1 O1W 78.35(19) . . ?
O3W Eu1 O2W 134.95(19) . . ?
C2 C1 Eu1 177.8(4) . . ?
O1 C1 Eu1 60.2(3) . . ?
O1 C1 C2 119.7(5) . . ?
O1 C1 O2 121.7(5) . . ?
O2 C1 Eu1 61.6(3) . . ?
O2 C1 C2 118.6(5) . . ?
C3 C2 C1 120.1(5) . . ?
C6 C2 C1 121.8(5) . . ?
C6 C2 C3 118.0(5) . . ?
C2 C3 H3 117.9 . . ?
N1 C3 C2 124.2(5) . . ?
N1 C3 H3 117.9 . . ?
C5 C4 H4 118.2 . . ?
N1 C4 H4 118.2 . . ?
N1 C4 C5 123.7(5) . . ?
C4 C5 C6 118.3(5) . . ?
C4 C5 C7 120.1(4) . . ?
C6 C5 C7 121.7(5) . . ?
C2 C6 C5 118.8(5) . . ?
C2 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
O3 C7 C5 117.3(5) . . ?
O4 C7 C5 117.5(5) . . ?
O4 C7 O3 125.1(5) . . ?
C9 C8 Eu1 178.1(5) . . ?
O5 C8 Eu1 59.5(3) . . ?
O5 C8 C9 122.0(6) . . ?
O5 C8 O6 121.4(6) . . ?
O6 C8 Eu1 61.9(3) . . ?
O6 C8 C9 116.6(6) . . ?
C8 C9 H9A 108.5 . . ?
C8 C9 H9B 108.5 . . ?
C9 C9 C8 115.0(8) 3_575 . ?
C9 C9 H9A 108.5 3_575 . ?
C9 C9 H9B 108.5 3_575 . ?
H9A C9 H9B 107.5 . . ?
C3 N1 C4 116.9(5) . . ?
C1 O1 Eu1 94.5(3) . . ?
C1 O2 Eu1 92.8(3) . . ?
C7 O3 Eu1 136.7(3) . 2_646 ?
C7 O4 Eu1 171.9(4) . 3_676 ?
C8 O5 Eu1 95.2(4) . . ?
C8 O6 Eu1 92.7(4) . . ?
Eu1 O1W H1WA 109.3 . . ?
Eu1 O1W H1WB 109.5 . . ?
H1WA O1W H1WB 108.2 . . ?
Eu1 O2W H2WA 109.2 . . ?
Eu1 O2W H2WB 109.5 . . ?
H2WA O2W H2WB 109.8 . . ?
Eu1 O3W H3WA 109.2 . . ?
Eu1 O3W H3WB 109.7 . . ?
H3WA O3W H3WB 108.2 . . ?
H4WA O4W H4WB 108.0 . . ?
H5WA O5W H5WB 108.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Eu1 C1 C2 C3 79(10) . . . . ?
Eu1 C1 C2 C6 -100(9) . . . . ?
Eu1 C8 C9 C9 -163(17) . . . 3_575 ?
C1 Eu1 C8 C9 -163(18) . . . . ?
C1 Eu1 C8 O5 56.0(5) . . . . ?
C1 Eu1 C8 O6 -125.4(4) . . . . ?
C1 Eu1 O5 C8 -131.2(4) . . . . ?
C1 Eu1 O6 C8 69.6(5) . . . . ?
C1 C2 C3 N1 -178.6(5) . . . . ?
C1 C2 C6 C5 -180.0(4) . . . . ?
C2 C1 O1 Eu1 -177.4(4) . . . . ?
C2 C1 O2 Eu1 177.5(4) . . . . ?
C2 C3 N1 C4 -1.2(8) . . . . ?
C3 C2 C6 C5 0.5(7) . . . . ?
C4 C5 C6 C2 -1.4(7) . . . . ?
C4 C5 C7 O3 -8.3(7) . . . . ?
C4 C5 C7 O4 169.5(5) . . . . ?
C5 C4 N1 C3 0.2(8) . . . . ?
C5 C7 O3 Eu1 -101.1(5) . . . 2_646 ?
C5 C7 O4 Eu1 -92(3) . . . 3_676 ?
C6 C2 C3 N1 0.9(8) . . . . ?
C6 C5 C7 O3 171.5(5) . . . . ?
C6 C5 C7 O4 -10.6(7) . . . . ?
C7 C5 C6 C2 178.7(4) . . . . ?
C8 Eu1 C1 C2 -118(9) . . . . ?
C8 Eu1 C1 O1 153.7(3) . . . . ?
C8 Eu1 C1 O2 -23.5(4) . . . . ?
C8 Eu1 O1 C1 -36.9(5) . . . . ?
C8 Eu1 O2 C1 159.2(3) . . . . ?
C9 C8 O5 Eu1 -178.6(6) . . . . ?
C9 C8 O6 Eu1 178.7(6) . . . . ?
N1 C4 C5 C6 1.1(8) . . . . ?
N1 C4 C5 C7 -179.0(5) . . . . ?
O1 Eu1 C1 C2 88(9) . . . . ?
O1 Eu1 C1 O2 -177.3(5) . . . . ?
O1 Eu1 C8 C9 -146(18) . . . . ?
O1 Eu1 C8 O5 72.8(5) . . . . ?
O1 Eu1 C8 O6 -108.6(5) . . . . ?
O1 Eu1 O2 C1 1.5(3) . . . . ?
O1 Eu1 O5 C8 -128.5(4) . . . . ?
O1 Eu1 O6 C8 102.3(5) . . . . ?
O1 C1 C2 C3 165.9(5) . . . . ?
O1 C1 C2 C6 -13.6(8) . . . . ?
O1 C1 O2 Eu1 -2.8(5) . . . . ?
O2 Eu1 C1 C2 -95(10) . . . . ?
O2 Eu1 C1 O1 177.3(5) . . . . ?
O2 Eu1 C8 C9 -173(18) . . . . ?
O2 Eu1 C8 O5 46.0(4) . . . . ?
O2 Eu1 C8 O6 -135.4(5) . . . . ?
O2 Eu1 O1 C1 -1.5(3) . . . . ?
O2 Eu1 O5 C8 -132.2(4) . . . . ?
O2 Eu1 O6 C8 48.7(5) . . . . ?
O2 C1 C2 C3 -14.3(7) . . . . ?
O2 C1 C2 C6 166.1(5) . . . . ?
O2 C1 O1 Eu1 2.8(6) . . . . ?
O3 Eu1 C1 C2 47(9) 2_656 . . . ?
O3 Eu1 C1 O1 -40.6(3) 2_656 . . . ?
O3 Eu1 C1 O2 142.1(3) 2_656 . . . ?
O3 Eu1 C8 C9 44(18) 2_656 . . . ?
O3 Eu1 C8 O5 -97.3(5) 2_656 . . . ?
O3 Eu1 C8 O6 81.3(6) 2_656 . . . ?
O3 Eu1 O1 C1 137.5(3) 2_656 . . . ?
O3 Eu1 O2 C1 -41.8(3) 2_656 . . . ?
O3 Eu1 O5 C8 118.1(4) 2_656 . . . ?
O3 Eu1 O6 C8 -128.5(4) 2_656 . . . ?
O3 C7 O4 Eu1 86(3) . . . 3_676 ?
O4 Eu1 C1 C2 122(9) 3_676 . . . ?
O4 Eu1 C1 O1 33.8(4) 3_676 . . . ?
O4 Eu1 C1 O2 -143.5(3) 3_676 . . . ?
O4 Eu1 C8 C9 -37(18) 3_676 . . . ?
O4 Eu1 C8 O5 -178.2(4) 3_676 . . . ?
O4 Eu1 C8 O6 0.4(5) 3_676 . . . ?
O4 Eu1 O1 C1 -149.4(3) 3_676 . . . ?
O4 Eu1 O2 C1 48.2(4) 3_676 . . . ?
O4 Eu1 O5 C8 2.2(5) 3_676 . . . ?
O4 Eu1 O6 C8 -179.6(5) 3_676 . . . ?
O4 C7 O3 Eu1 81.2(7) . . . 2_646 ?
O5 Eu1 C1 C2 -97(9) . . . . ?
O5 Eu1 C1 O1 174.9(3) . . . . ?
O5 Eu1 C1 O2 -2.3(3) . . . . ?
O5 Eu1 C8 C9 141(18) . . . . ?
O5 Eu1 C8 O6 178.6(7) . . . . ?
O5 Eu1 O1 C1 -6.2(4) . . . . ?
O5 Eu1 O2 C1 177.6(3) . . . . ?
O5 Eu1 O6 C8 -0.8(4) . . . . ?
O5 C8 C9 C9 -22.3(15) . . . 3_575 ?
O5 C8 O6 Eu1 1.4(8) . . . . ?
O6 Eu1 C1 C2 -145(9) . . . . ?
O6 Eu1 C1 O1 126.8(3) . . . . ?
O6 Eu1 C1 O2 -50.4(4) . . . . ?
O6 Eu1 C8 C9 -38(18) . . . . ?
O6 Eu1 C8 O5 -178.6(7) . . . . ?
O6 Eu1 O1 C1 -76.7(4) . . . . ?
O6 Eu1 O2 C1 140.3(3) . . . . ?
O6 Eu1 O5 C8 0.8(4) . . . . ?
O6 C8 C9 C9 160.5(10) . . . 3_575 ?
O6 C8 O5 Eu1 -1.5(8) . . . . ?
O1W Eu1 C1 C2 -24(9) . . . . ?
O1W Eu1 C1 O1 -111.5(3) . . . . ?
O1W Eu1 C1 O2 71.3(3) . . . . ?
O1W Eu1 C8 C9 117(18) . . . . ?
O1W Eu1 C8 O5 -24.0(4) . . . . ?
O1W Eu1 C8 O6 154.6(5) . . . . ?
O1W Eu1 O1 C1 65.0(3) . . . . ?
O1W Eu1 O2 C1 -101.1(3) . . . . ?
O1W Eu1 O5 C8 155.8(5) . . . . ?
O1W Eu1 O6 C8 -30.2(5) . . . . ?
O2W Eu1 C1 C2 180(100) . . . . ?
O2W Eu1 C1 O1 92.1(3) . . . . ?
O2W Eu1 C1 O2 -85.1(3) . . . . ?
O2W Eu1 C8 C9 -104(18) . . . . ?
O2W Eu1 C8 O5 114.9(4) . . . . ?
O2W Eu1 C8 O6 -66.5(5) . . . . ?
O2W Eu1 O1 C1 -79.5(3) . . . . ?
O2W Eu1 O2 C1 85.6(3) . . . . ?
O2W Eu1 O5 C8 -61.7(4) . . . . ?
O2W Eu1 O6 C8 105.3(5) . . . . ?
O3W Eu1 C1 C2 -9(10) . . . . ?
O3W Eu1 C1 O1 -97.1(4) . . . . ?
O3W Eu1 C1 O2 85.6(4) . . . . ?
O3W Eu1 C8 C9 43(18) . . . . ?
O3W Eu1 C8 O5 -98.4(5) . . . . ?
O3W Eu1 C8 O6 80.2(5) . . . . ?
O3W Eu1 O1 C1 127.7(4) . . . . ?
O3W Eu1 O2 C1 -133.8(4) . . . . ?
O3W Eu1 O5 C8 75.3(4) . . . . ?
O3W Eu1 O6 C8 -91.6(5) . . . . ?

_database_code_depnum_ccdc_archive 'CCDC 967479'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_CCDC

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         C9H11NO9Tb,2(H2O)
_chemical_formula_sum            'C9 H15 N O11 Tb'
_chemical_formula_weight         472.14

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   p21/c

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

_cell_length_a                   15.8734(12)
_cell_length_b                   13.4525(10)
_cell_length_c                   6.6309(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.8620(10)
_cell_angle_gamma                90.00
_cell_volume                     1402.63(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5830
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      28.39

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.236
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             916
_exptl_absorpt_coefficient_mu    5.102
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.607
_exptl_absorpt_correction_T_max  0.654
_exptl_absorpt_process_details   ?

_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7014
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_av_sigmaI/netI    0.0225
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         1.99
_diffrn_reflns_theta_max         25.19
_reflns_number_total             2503
_reflns_number_gt                2380
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL-XP (Bruker, 2004)'
_computing_publication_material  SHELXL-97

_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)+(0.0338P)²+3.7984P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0067(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2503
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0239
_refine_ls_R_factor_gt           0.0227
_refine_ls_wR_factor_ref         0.0626
_refine_ls_wR_factor_gt          0.0618
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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
Tb1 Tb 0.251177(11) -0.060801(13) 0.46505(3) 0.01937(11) Uani 1 1 d . . .
O1 O 0.31965(18) -0.2033(2) 0.3655(5) 0.0319(7) Uani 1 1 d . . .
O1W O 0.1476(2) -0.1789(3) 0.5770(8) 0.0629(13) Uani 1 1 d . . .
H1 H 0.1025 -0.1791 0.4917 0.094 Uiso 1 1 d R . .
H2 H 0.1348 -0.1606 0.6917 0.094 Uiso 1 1 d R . .
O2 O 0.31887(17) -0.3627(2) 0.2840(4) 0.0235(6) Uani 1 1 d . . .
O2W O 0.3061(2) -0.0246(2) 0.1402(5) 0.0384(8) Uani 1 1 d . . .
H3 H 0.3582 -0.0080 0.1643 0.058 Uiso 1 1 d R . .
H4 H 0.2785 0.0237 0.0809 0.058 Uiso 1 1 d R . .
O3 O 0.71921(17) -0.1235(2) 0.5553(5) 0.0262(6) Uani 1 1 d . . .
O3W O 0.2009(2) 0.0271(3) 0.7541(5) 0.0383(8) Uani 1 1 d . . .
H5 H 0.1541 0.0016 0.7767 0.057 Uiso 1 1 d R . .
H6 H 0.1937 0.0886 0.7282 0.057 Uiso 1 1 d R . .
O4 O 0.61040(18) -0.0283(2) 0.4415(5) 0.0263(6) Uani 1 1 d . . .
O5 O 0.1527(2) -0.1207(3) 0.1537(7) 0.0577(12) Uani 1 1 d . . .
O6 O 0.11453(19) 0.0114(2) 0.3073(6) 0.0379(8) Uani 1 1 d . . .
N1 N 0.5798(2) -0.3810(2) 0.4163(5) 0.0202(7) Uani 1 1 d . . .
C1 C 0.3562(2) -0.2830(3) 0.3376(5) 0.0166(7) Uani 1 1 d . . .
C2 C 0.4521(2) -0.2836(3) 0.3762(5) 0.0148(7) Uani 1 1 d . . .
C3 C 0.4954(2) -0.3741(3) 0.3795(5) 0.0171(7) Uani 1 1 d . . .
H3A H 0.4639 -0.4321 0.3548 0.021 Uiso 1 1 calc R . .
C4 C 0.6239(2) -0.2968(3) 0.4510(6) 0.0196(8) Uani 1 1 d . . .
H4A H 0.6827 -0.3012 0.4802 0.024 Uiso 1 1 calc R . .
C5 C 0.5871(2) -0.2034(3) 0.4460(5) 0.0165(7) Uani 1 1 d . . .
C6 C 0.4990(2) -0.1969(3) 0.4082(5) 0.0172(7) Uani 1 1 d . . .
H6A H 0.4720 -0.1354 0.4043 0.021 Uiso 1 1 calc R . .
C7 C 0.6424(2) -0.1120(3) 0.4824(6) 0.0184(8) Uani 1 1 d . . .
C8 C 0.1007(3) -0.0514(3) 0.1672(8) 0.0346(11) Uani 1 1 d . . .
C9 C 0.0219(4) -0.0481(4) 0.0106(10) 0.0513(15) Uani 1 1 d . . .
H9A H 0.0379 -0.0664 -0.1206 0.062 Uiso 1 1 calc R . .
H9B H -0.0177 -0.0979 0.0461 0.062 Uiso 1 1 calc R . .
O4W O 0.1616(3) -0.7276(3) 0.2987(9) 0.0759(15) Uani 1 1 d . . .
H7 H 0.1553 -0.7494 0.1772 0.114 Uiso 1 1 d R . .
H8 H 0.2082 -0.7522 0.3551 0.114 Uiso 1 1 d R . .
O5W O 0.0280(3) -0.6616(4) -0.0087(9) 0.0884(17) Uani 1 1 d . . .
H9 H 0.0443 -0.6061 -0.0510 0.133 Uiso 1 1 d R . .
H10 H 0.0348 -0.6612 0.1207 0.133 Uiso 1 1 d R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Tb1 O1 2.342(3) . ?
Tb1 O2 2.462(3) 4_556 ?
Tb1 O6 2.474(3) . ?
Tb1 O1W 2.472(3) . ?
Tb1 O3W 2.475(3) . ?
Tb1 O2W 2.480(3) . ?
Tb1 O4 2.505(3) 3_656 ?
Tb1 O3 2.531(3) 3_656 ?
Tb1 O5 2.544(4) . ?
Tb1 C7 2.867(4) 3_656 ?
Tb1 C8 2.886(5) . ?
O1 C1 1.245(5) . ?
O1W H1 0.8501 . ?
O1W H2 0.8501 . ?
O2 C1 1.253(5) . ?
O2 Tb1 2.462(3) 4 ?
O2W H3 0.8500 . ?
O2W H4 0.8500 . ?
O3 C7 1.259(5) . ?
O3 Tb1 2.531(3) 3_656 ?
O3W H5 0.8501 . ?
O3W H6 0.8499 . ?
O4 C7 1.250(5) . ?
O4 Tb1 2.505(3) 3_656 ?
O5 C8 1.256(6) . ?
O6 C8 1.252(6) . ?
N1 C3 1.332(5) . ?
N1 C4 1.334(5) . ?
C1 C2 1.509(5) . ?
C2 C6 1.384(5) . ?
C2 C3 1.397(5) . ?
C3 H3A 0.9300 . ?
C4 C5 1.385(5) . ?
C4 H4A 0.9300 . ?
C5 C6 1.388(5) . ?
C5 C7 1.510(5) . ?
C6 H6A 0.9300 . ?
C7 Tb1 2.867(4) 3_656 ?
C8 C9 1.513(7) . ?
C9 C9 1.467(10) 3 ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
O4W H7 0.8500 . ?
O4W H8 0.8500 . ?
O5W H9 0.8500 . ?
O5W H10 0.8500 . ?

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 O2 74.66(10) . 4_556 ?
O1 Tb1 O6 128.01(11) . . ?
O2 Tb1 O6 141.39(11) 4_556 . ?
O1 Tb1 O1W 84.94(13) . . ?
O2 Tb1 O1W 72.75(12) 4_556 . ?
O6 Tb1 O1W 78.39(12) . . ?
O1 Tb1 O3W 145.11(11) . . ?
O2 Tb1 O3W 71.55(10) 4_556 . ?
O6 Tb1 O3W 77.47(11) . . ?
O1W Tb1 O3W 77.09(15) . . ?
O1 Tb1 O2W 71.59(12) . . ?
O2 Tb1 O2W 131.59(11) 4_556 . ?
O6 Tb1 O2W 87.02(12) . . ?
O1W Tb1 O2W 135.59(14) . . ?
O3W Tb1 O2W 140.13(11) . . ?
O1 Tb1 O4 92.07(10) . 3_656 ?
O2 Tb1 O4 73.88(9) 4_556 3_656 ?
O6 Tb1 O4 127.26(10) . 3_656 ?
O1W Tb1 O4 146.08(13) . 3_656 ?
O3W Tb1 O4 86.82(11) . 3_656 ?
O2W Tb1 O4 73.75(11) . 3_656 ?
O1 Tb1 O3 133.63(10) . 3_656 ?
O2 Tb1 O3 113.12(9) 4_556 3_656 ?
O6 Tb1 O3 75.61(10) . 3_656 ?
O1W Tb1 O3 141.42(12) . 3_656 ?
O3W Tb1 O3 69.82(11) . 3_656 ?
O2W Tb1 O3 70.82(10) . 3_656 ?
O4 Tb1 O3 51.79(9) 3_656 3_656 ?
O1 Tb1 O5 76.68(11) . . ?
O2 Tb1 O5 135.41(12) 4_556 . ?
O6 Tb1 O5 51.33(11) . . ?
O1W Tb1 O5 71.35(16) . . ?
O3W Tb1 O5 123.52(12) . . ?
O2W Tb1 O5 66.90(13) . . ?
O4 Tb1 O5 140.63(13) 3_656 . ?
O3 Tb1 O5 111.41(12) 3_656 . ?
O1 Tb1 C7 114.16(11) . 3_656 ?
O2 Tb1 C7 93.08(10) 4_556 3_656 ?
O6 Tb1 C7 101.61(11) . 3_656 ?
O1W Tb1 C7 152.84(14) . 3_656 ?
O3W Tb1 C7 76.45(11) . 3_656 ?
O2W Tb1 C7 71.02(10) . 3_656 ?
O4 Tb1 C7 25.80(10) 3_656 3_656 ?
O3 Tb1 C7 26.02(10) 3_656 3_656 ?
O5 Tb1 C7 129.93(13) . 3_656 ?
O1 Tb1 C8 102.45(12) . . ?
O2 Tb1 C8 146.00(12) 4_556 . ?
O6 Tb1 C8 25.56(12) . . ?
O1W Tb1 C8 73.25(14) . . ?
O3W Tb1 C8 100.63(13) . . ?
O2W Tb1 C8 75.74(14) . . ?
O4 Tb1 C8 139.82(11) 3_656 . ?
O3 Tb1 C8 93.61(11) 3_656 . ?
O5 Tb1 C8 25.78(12) . . ?
C7 Tb1 C8 117.79(12) 3_656 . ?
C1 O1 Tb1 172.0(3) . . ?
Tb1 O1W H1 109.7 . . ?
Tb1 O1W H2 109.4 . . ?
H1 O1W H2 108.2 . . ?
C1 O2 Tb1 137.3(2) . 4 ?
Tb1 O2W H3 109.7 . . ?
Tb1 O2W H4 109.4 . . ?
H3 O2W H4 108.2 . . ?
C7 O3 Tb1 92.1(2) . 3_656 ?
Tb1 O3W H5 109.0 . . ?
Tb1 O3W H6 111.0 . . ?
H5 O3W H6 109.4 . . ?
C7 O4 Tb1 93.5(2) . 3_656 ?
C8 O5 Tb1 92.5(3) . . ?
C8 O6 Tb1 96.0(3) . . ?
C3 N1 C4 117.5(3) . . ?
O1 C1 O2 124.6(3) . . ?
O1 C1 C2 117.3(3) . . ?
O2 C1 C2 118.1(3) . . ?
C6 C2 C3 118.6(3) . . ?
C6 C2 C1 122.0(3) . . ?
C3 C2 C1 119.3(3) . . ?
N1 C3 C2 123.0(3) . . ?
N1 C3 H3A 118.5 . . ?
C2 C3 H3A 118.5 . . ?
N1 C4 C5 123.9(3) . . ?
N1 C4 H4A 118.1 . . ?
C5 C4 H4A 118.1 . . ?
C4 C5 C6 118.1(3) . . ?
C4 C5 C7 120.1(3) . . ?
C6 C5 C7 121.8(3) . . ?
C2 C6 C5 118.8(3) . . ?
C2 C6 H6A 120.6 . . ?
C5 C6 H6A 120.6 . . ?
O4 C7 O3 122.5(3) . . ?
O4 C7 C5 119.3(3) . . ?
O3 C7 C5 118.2(3) . . ?
O4 C7 Tb1 60.70(19) . 3_656 ?
O3 C7 Tb1 61.90(19) . 3_656 ?
C5 C7 Tb1 177.7(3) . 3_656 ?
O6 C8 O5 120.2(4) . . ?
O6 C8 C9 122.3(4) . . ?
O5 C8 C9 117.5(4) . . ?
O6 C8 Tb1 58.5(2) . . ?
O5 C8 Tb1 61.7(2) . . ?
C9 C8 Tb1 179.1(3) . . ?
C9 C9 C8 115.4(6) 3 . ?
C9 C9 H9A 108.4 3 . ?
C8 C9 H9A 108.4 . . ?
C9 C9 H9B 108.4 3 . ?
C8 C9 H9B 108.4 . . ?
H9A C9 H9B 107.5 . . ?
H7 O4W H8 105.4 . . ?
H9 O5W H10 109.0 . . ?

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 Tb1 O1 C1 18.4(19) 4_556 . . . ?
O6 Tb1 O1 C1 -126.1(19) . . . . ?
O1W Tb1 O1 C1 -55.1(19) . . . . ?
O3W Tb1 O1 C1 4(2) . . . . ?
O2W Tb1 O1 C1 163.1(19) . . . . ?
O4 Tb1 O1 C1 91.0(19) 3_656 . . . ?
O3 Tb1 O1 C1 125.9(19) 3_656 . . . ?
O5 Tb1 O1 C1 -127.1(19) . . . . ?
C7 Tb1 O1 C1 104.8(19) 3_656 . . . ?
C8 Tb1 O1 C1 -126.7(19) . . . . ?
O1 Tb1 O5 C8 179.1(4) . . . . ?
O2 Tb1 O5 C8 127.9(3) 4_556 . . . ?
O6 Tb1 O5 C8 0.1(3) . . . . ?
O1W Tb1 O5 C8 90.0(3) . . . . ?
O3W Tb1 O5 C8 30.4(4) . . . . ?
O2W Tb1 O5 C8 -105.5(4) . . . . ?
O4 Tb1 O5 C8 -104.2(3) 3_656 . . . ?
O3 Tb1 O5 C8 -49.0(4) 3_656 . . . ?
C7 Tb1 O5 C8 -70.4(4) 3_656 . . . ?
O1 Tb1 O6 C8 -1.3(4) . . . . ?
O2 Tb1 O6 C8 -117.4(3) 4_556 . . . ?
O1W Tb1 O6 C8 -75.4(3) . . . . ?
O3W Tb1 O6 C8 -154.5(3) . . . . ?
O2W Tb1 O6 C8 62.4(3) . . . . ?
O4 Tb1 O6 C8 129.4(3) 3_656 . . . ?
O3 Tb1 O6 C8 133.4(3) 3_656 . . . ?
O5 Tb1 O6 C8 -0.1(3) . . . . ?
C7 Tb1 O6 C8 132.4(3) 3_656 . . . ?
Tb1 O1 C1 O2 89.3(19) . . . . ?
Tb1 O1 C1 C2 -89.2(19) . . . . ?
Tb1 O2 C1 O1 81.0(5) 4 . . . ?
Tb1 O2 C1 C2 -100.5(4) 4 . . . ?
O1 C1 C2 C6 -10.6(5) . . . . ?
O2 C1 C2 C6 170.9(3) . . . . ?
O1 C1 C2 C3 169.6(3) . . . . ?
O2 C1 C2 C3 -8.9(5) . . . . ?
C4 N1 C3 C2 -0.1(5) . . . . ?
C6 C2 C3 N1 1.5(5) . . . . ?
C1 C2 C3 N1 -178.7(3) . . . . ?
C3 N1 C4 C5 -1.6(6) . . . . ?
N1 C4 C5 C6 1.8(6) . . . . ?
N1 C4 C5 C7 -178.5(3) . . . . ?
C3 C2 C6 C5 -1.2(5) . . . . ?
C1 C2 C6 C5 179.0(3) . . . . ?
C4 C5 C6 C2 -0.3(5) . . . . ?
C7 C5 C6 C2 -179.9(3) . . . . ?
Tb1 O4 C7 O3 3.4(4) 3_656 . . . ?
Tb1 O4 C7 C5 -177.4(3) 3_656 . . . ?
Tb1 O3 C7 O4 -3.3(4) 3_656 . . . ?
Tb1 O3 C7 C5 177.4(3) 3_656 . . . ?
C4 C5 C7 O4 167.0(4) . . . . ?
C6 C5 C7 O4 -13.3(5) . . . . ?
C4 C5 C7 O3 -13.6(5) . . . . ?
C6 C5 C7 O3 166.0(3) . . . . ?
C4 C5 C7 Tb1 79(7) . . . 3_656 ?
C6 C5 C7 Tb1 -101(7) . . . 3_656 ?
Tb1 O6 C8 O5 0.1(5) . . . . ?
Tb1 O6 C8 C9 179.6(5) . . . . ?
Tb1 O5 C8 O6 -0.1(5) . . . . ?
Tb1 O5 C8 C9 -179.6(5) . . . . ?
O1 Tb1 C8 O6 178.9(3) . . . . ?
O2 Tb1 C8 O6 98.0(3) 4_556 . . . ?
O1W Tb1 C8 O6 98.2(3) . . . . ?
O3W Tb1 C8 O6 25.3(3) . . . . ?
O2W Tb1 C8 O6 -114.0(3) . . . . ?
O4 Tb1 C8 O6 -72.5(4) 3_656 . . . ?
O3 Tb1 C8 O6 -44.9(3) 3_656 . . . ?
O5 Tb1 C8 O6 179.9(5) . . . . ?
C7 Tb1 C8 O6 -54.9(3) 3_656 . . . ?
O1 Tb1 C8 O5 -0.9(4) . . . . ?
O2 Tb1 C8 O5 -81.9(4) 4_556 . . . ?
O6 Tb1 C8 O5 -179.9(5) . . . . ?
O1W Tb1 C8 O5 -81.7(3) . . . . ?
O3W Tb1 C8 O5 -154.6(3) . . . . ?
O2W Tb1 C8 O5 66.1(3) . . . . ?
O4 Tb1 C8 O5 107.7(3) 3_656 . . . ?
O3 Tb1 C8 O5 135.3(3) 3_656 . . . ?
C7 Tb1 C8 O5 125.2(3) 3_656 . . . ?
O1 Tb1 C8 C9 23(29) . . . . ?
O2 Tb1 C8 C9 -58(29) 4_556 . . . ?
O6 Tb1 C8 C9 -156(29) . . . . ?
O1W Tb1 C8 C9 -58(29) . . . . ?
O3W Tb1 C8 C9 -131(29) . . . . ?
O2W Tb1 C8 C9 90(29) . . . . ?
O4 Tb1 C8 C9 131(29) 3_656 . . . ?
O3 Tb1 C8 C9 159(29) 3_656 . . . ?
O5 Tb1 C8 C9 24(29) . . . . ?
C7 Tb1 C8 C9 149(29) 3_656 . . . ?
O6 C8 C9 C9 19.5(11) . . . 3 ?
O5 C8 C9 C9 -161.0(7) . . . 3 ?
Tb1 C8 C9 C9 176(100) . . . 3 ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.19
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.798
_refine_diff_density_min         -0.697
_refine_diff_density_rms         0.117
_database_code_depnum_ccdc_archive 'CCDC 967480'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_CCDC

_audit_creation_date             2014-03-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.02.28 svn.r2899 for OlexSys, GUI svn.r4781)
;
_chemical_formula_moiety         'C9 H11 Er N O9, 2(H2 O)'
_chemical_formula_sum            'C9 H15 Er N O11'
_chemical_formula_weight         480.48
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Er -0.12730 5.10226 27.65630 16.42850 14.97790 2.98233 2.07356 0.22354 11.36040
105.70300 5.92046022415
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        P21/c
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   15.8585(14)
_cell_length_b                   13.4190(11)
_cell_length_c                   6.6158(6)
_cell_angle_alpha                90
_cell_angle_beta                 97.925(1)
_cell_angle_gamma                90
_cell_volume                     1394.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2367
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      27.44

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.216
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             928.1655
_exptl_absorpt_coefficient_mu    6.078
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5886
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'

_exptl_special_details           
; 
 ? 
;
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_unetI/netI     0.0495
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            8488
_diffrn_reflns_theta_full        25.1929
_diffrn_reflns_theta_max         25.19
_diffrn_reflns_theta_min         1.30
_diffrn_measured_fraction_theta_full 0.9996
_diffrn_measured_fraction_theta_max 0.9996
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              18
_reflns_limit_h_min              -18
_reflns_limit_k_max              16
_reflns_limit_k_min              0
_reflns_limit_l_max              7
_reflns_limit_l_min              0
_reflns_number_gt                2087
_reflns_number_total             2493
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2013)'
_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_refine_diff_density_max         1.5058
_refine_diff_density_min         -0.9365
_refine_diff_density_rms         0.2347
_refine_ls_d_res_high            0.8348
_refine_ls_d_res_low             15.7070
_refine_ls_goodness_of_fit_ref   1.0237
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    25
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2493
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0374
_refine_ls_restrained_S_all      1.0237
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0564P)²+12.9048P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1002
_refine_ls_wR_factor_ref         0.1085
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O4W(N1,O1,O2,O3,O4,O5,O6,O1W), O4W(H4Wa,H4Wb), O5W(H5Wa,H5Wb)
2.b Rotating group:
 O1W(H1Wa,H1Wb), O2W(H2Wa,H2Wb), O3W(H3Wa,H3Wb)
2.c Secondary CH2 refined with riding coordinates:
 C9(H9a,H9b)
2.d Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6)
;
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_refinement_flags_posn
Er1 Er 0.24882(2) 0.56099(2) 1.03600(6) 0.01985(16) Uani 1.000000 .
C1 C 0.1429(5) 0.3885(6) 0.9833(12) 0.0236(18) Uani 1.000000 .
C2 C 0.0868(5) 0.2968(6) 0.9461(12) 0.0208(17) Uani 1.000000 .
C3 C 0.1244(5) 0.2032(6) 0.9521(12) 0.0247(18) Uani 1.000000 .
C4 C -0.0045(5) 0.1263(6) 0.8797(11) 0.0206(17) Uani 1.000000 .
C5 C -0.0485(5) 0.2161(6) 0.8770(11) 0.0184(16) Uani 1.000000 .
C6 C -0.0003(5) 0.3037(6) 0.9074(11) 0.0192(17) Uani 1.000000 .
C7 C -0.1435(5) 0.2169(6) 0.8367(12) 0.0196(17) Uani 1.000000 .
C8 C 0.3995(6) 0.5519(7) 1.3333(17) 0.038(2) Uani 1.000000 .
C9 C 0.4781(7) 0.5486(8) 1.4904(19) 0.052(3) Uani 1.000000 .
O4W O 0.33738(19) 0.2719(3) 0.7084(7) 0.086(3) Uani 1.000000 .
N1 N 0.07988(19) 0.11876(17) 0.9170(6) 0.0225(15) Uani 1.000000 G
O1 O 0.11087(15) 0.47319(16) 0.9428(5) 0.0298(14) Uani 1.000000 G
O2 O 0.21950(15) 0.37756(18) 1.0561(4) 0.0295(14) Uani 1.000000 G
O3 O -0.18108(18) 0.1369(3) 0.7828(6) 0.0284(14) Uani 1.000000 G
O4 O -0.18102(15) 0.2967(3) 0.8655(7) 0.0367(16) Uani 1.000000 G
O5 O 0.38482(16) 0.4879(2) 1.1928(6) 0.0410(17) Uani 1.000000 G
O6 O 0.3468(2) 0.6211(3) 1.3460(7) 0.063(2) Uani 1.000000 G
O1W O 0.30052(19) 0.4736(3) 0.7499(5) 0.0442(18) Uani 1.000000 G
O2W O 0.1949(5) 0.5241(5) 1.3588(10) 0.0466(19) Uani 1.000000 .
O3W O 0.3520(5) 0.6777(6) 0.9237(16) 0.070(3) Uani 1.000000 .
O5W O 0.5278(7) 0.6590(9) 0.9922(19) 0.090(3) Uani 1.000000 .
H3 H 0.1833(5) 0.1990(6) 0.9819(12) 0.030(2) Uiso 1.000000 R
H4 H -0.0360(5) 0.0680(6) 0.8539(11) 0.025(2) Uiso 1.000000 R
H6 H -0.0269(5) 0.3655(6) 0.9014(11) 0.023(2) Uiso 1.000000 R
H9a H 0.5178(7) 0.5986(8) 1.4557(19) 0.062(4) Uiso 1.000000 R
H9b H 0.4621(7) 0.5663(8) 1.6221(19) 0.062(4) Uiso 1.000000 R
H1Wa H 0.307(6) 0.5152(12) 0.656(6) 0.066(3) Uiso 1.000000 GR
H1Wb H 0.265(3) 0.429(5) 0.704(9) 0.066(3) Uiso 1.000000 GR
H2Wa H 0.218(5) 0.563(5) 1.451(4) 0.070(3) Uiso 1.000000 GR
H2Wb H 0.207(6) 0.464(2) 1.393(8) 0.070(3) Uiso 1.000000 GR
H3Wa H 0.397(3) 0.6465(17) 0.908(18) 0.105(4) Uiso 1.000000 GR
H3Wb H 0.364(6) 0.723(5) 1.013(9) 0.105(4) Uiso 1.000000 GR
H4Wa H 0.291(6) 0.248(12) 0.65(2) 0.129(5) Uiso 1.000000 G
H4Wb H 0.346(10) 0.251(12) 0.831(9) 0.129(5) Uiso 1.000000 G
H5Wa H 0.544(12) 0.623(11) 0.899(16) 0.135(5) Uiso 1.000000 G
H5Wb H 0.543(13) 0.631(12) 1.107(11) 0.135(5) Uiso 1.000000 G


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 2.486(2) . ?
Er1 O2 2.512(2) . ?
Er1 O3 2.453(3) 2_556 ?
Er1 O4 2.328(3) 3_567 ?
Er1 O5 2.464(3) . ?
Er1 O6 2.529(3) . ?
Er1 O1W 2.461(3) . ?
Er1 O2W 2.457(6) . ?
Er1 O3W 2.454(7) . ?
C1 C2 1.518(11) . ?
C1 O1 1.259(9) . ?
C1 O2 1.252(9) . ?
C2 C3 1.389(11) . ?
C2 C6 1.372(11) . ?
C3 N1 1.338(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.391(11) . ?
C4 N1 1.331(9) . ?
C4 H4 0.9300 . ?
C5 C6 1.401(11) . ?
C5 C7 1.493(11) . ?
C6 H6 0.9300 . ?
C7 O3 1.255(8) . ?
C7 O4 1.252(9) . ?
C8 C9 1.510(14) . ?
C8 O5 1.263(11) . ?
C8 O6 1.260(11) . ?
C9 C9 1.47(2) 3_668 ?
C9 H9a 0.9700 . ?
C9 H9b 0.9700 . ?
O4W H4Wa 0.8500 . ?
O4W H4Wb 0.8500 . ?
O1W H1Wa 0.8500 . ?
O1W H1Wb 0.8500 . ?
O2W H2Wa 0.8500 . ?
O2W H2Wb 0.8500 . ?
O3W H3Wa 0.8500 . ?
O3W H3Wb 0.8500 . ?
O5W H5Wa 0.8500 . ?
O5W H5Wb 0.8500 . ?

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 Er1 O1 52.11(5) . . ?
O3 Er1 O1 73.60(10) 2_556 . ?
O3 Er1 O2 112.98(10) 2_556 . ?
O4 Er1 O1 91.93(8) 3_567 . ?
O4 Er1 O2 133.86(8) 3_567 . ?
O4 Er1 O3 74.66(8) 3_567 2_556 ?
O5 Er1 O1 127.21(11) . . ?
O5 Er1 O2 75.24(8) . . ?
O5 Er1 O3 141.39(12) . 2_556 ?
O5 Er1 O4 128.31(12) . 3_567 ?
O6 Er1 O1 140.68(16) . . ?
O6 Er1 O2 111.54(13) . . ?
O6 Er1 O3 135.43(12) . 2_556 ?
O6 Er1 O4 76.54(14) . 3_567 ?
O6 Er1 O5 51.78(6) . . ?
O1W Er1 O1 87.63(9) . . ?
O1W Er1 O2 69.99(7) . . ?
O1W Er1 O3 71.91(13) . 2_556 ?
O1W Er1 O4 145.24(16) . 3_567 ?
O1W Er1 O5 76.65(9) . . ?
O1W Er1 O6 122.90(11) . . ?
O2W Er1 O1 73.76(19) . . ?
O2W Er1 O2 70.59(17) . . ?
O2W Er1 O3 131.8(2) . 2_556 ?
O2W Er1 O4 72.1(2) . 3_567 ?
O2W Er1 O5 86.8(2) . . ?
O2W Er1 O6 66.9(2) . . ?
O2W Er1 O1W 139.92(18) . . ?
O3W Er1 O1 145.9(2) . . ?
O3W Er1 O2 141.1(2) . . ?
O3W Er1 O3 72.9(2) . 2_556 ?
O3W Er1 O4 85.1(2) . 3_567 ?
O3W Er1 O5 78.46(19) . . ?
O3W Er1 O6 71.4(3) . . ?
O3W Er1 O1W 76.4(3) . . ?
O3W Er1 O2W 135.9(3) . . ?
O1 C1 C2 119.1(7) . . ?
O2 C1 C2 118.9(7) . . ?
O2 C1 O1 121.9(7) . . ?
C3 C2 C1 119.2(7) . . ?
C6 C2 C1 121.9(7) . . ?
C6 C2 C3 118.9(7) . . ?
N1 C3 C2 123.1(7) . . ?
H3 C3 C2 118.4(5) . . ?
H3 C3 N1 118.4(4) . . ?
N1 C4 C5 123.9(7) . . ?
H4 C4 C5 118.1(5) . . ?
H4 C4 N1 118.1(3) . . ?
C6 C5 C4 117.5(7) . . ?
C7 C5 C4 120.0(7) . . ?
C7 C5 C6 122.4(7) . . ?
C5 C6 C2 119.0(7) . . ?
H6 C6 C2 120.5(5) . . ?
H6 C6 C5 120.5(5) . . ?
O3 C7 C5 118.2(7) . . ?
O4 C7 C5 117.9(6) . . ?
O4 C7 O3 123.8(7) . . ?
O5 C8 C9 122.5(9) . . ?
O6 C8 C9 117.9(9) . . ?
O6 C8 O5 119.6(8) . . ?
C9 C9 C8 114.8(12) 3_668 . ?
H9a C9 C8 108.6(6) . . ?
H9b C9 C8 108.6(7) . . ?
H9b C9 H9a 107.5 . . ?
H4Wb O4W H4Wa 109.5 . . ?
C4 N1 C3 117.5(5) . . ?
C1 O1 Er1 93.4(4) . . ?
C1 O2 Er1 92.4(4) . . ?
C7 O3 Er1 137.2(4) . 2_546 ?
C7 O4 Er1 172.5(5) . 3_567 ?
C8 O5 Er1 95.8(5) . . ?
C8 O6 Er1 92.8(5) . . ?
H1Wa O1W Er1 109.5 . . ?
H1Wb O1W Er1 109.5 . . ?
H1Wb O1W H1Wa 109.5 . . ?
H2Wa O2W Er1 109.5 . . ?
H2Wb O2W Er1 109.5 . . ?
H2Wb O2W H2Wa 109.5 . . ?
H3Wa O3W Er1 109.5 . . ?
H3Wb O3W Er1 109.5 . . ?
H3Wb O3W H3Wa 109.5 . . ?
H5Wb O5W H5Wa 109.5 . . ?

_database_code_depnum_ccdc_archive 'CCDC 967481'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_CCDC

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         C9H9NO8Yb,2(H2O)
_chemical_formula_sum            'C9 H13 N O10 Yb'
_chemical_formula_weight         468.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Yb Yb -0.3850 5.5486 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   p-1

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

_cell_length_a                   5.3448(6)
_cell_length_b                   8.9517(10)
_cell_length_c                   15.6623(18)
_cell_angle_alpha                104.9120(10)
_cell_angle_beta                 93.0360(10)
_cell_angle_gamma                97.1570(10)
_cell_volume                     715.65(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3084
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      28.12

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.173
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             448
_exptl_absorpt_coefficient_mu    6.583
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3527
_exptl_absorpt_correction_T_max  0.5589
_exptl_absorpt_process_details   ?

_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       'ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3715
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_av_sigmaI/netI    0.0358
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.35
_diffrn_reflns_theta_max         25.20
_reflns_number_total             2527
_reflns_number_gt                2366
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL-XP (Bruker, 2004)'
_computing_publication_material  SHELXL-97

_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)+(0.0348P)²+0.1015P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0030(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2527
_refine_ls_number_parameters     195
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0261
_refine_ls_R_factor_gt           0.0245
_refine_ls_wR_factor_ref         0.0616
_refine_ls_wR_factor_gt          0.0607
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_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
Yb1 Yb 0.03059(4) 0.63775(2) 0.263059(12) 0.02087(10) Uani 1 1 d . . .
C1 C 0.3020(9) 0.7229(5) 0.4297(3) 0.0244(10) Uani 1 1 d . . .
C2 C 0.4658(9) 0.7468(5) 0.5144(3) 0.0218(10) Uani 1 1 d . . .
C3 C 0.6869(10) 0.8529(6) 0.5347(3) 0.0270(11) Uani 1 1 d . . .
H3A H 0.7254 0.9154 0.4967 0.032 Uiso 1 1 calc R . .
N1 N 0.8474(8) 0.8699(5) 0.6060(3) 0.0298(10) Uani 1 1 d . . .
C4 C 0.7933(9) 0.7763(6) 0.6586(3) 0.0263(11) Uani 1 1 d . . .
H4A H 0.9087 0.7825 0.7064 0.032 Uiso 1 1 calc R . .
C5 C 0.5715(9) 0.6697(5) 0.6451(3) 0.0224(10) Uani 1 1 d . . .
C7 C 0.5219(9) 0.5683(5) 0.7065(3) 0.0244(10) Uani 1 1 d . . .
C8 C -0.2575(10) 0.5263(6) 0.1016(3) 0.0303(12) Uani 1 1 d . . .
C9 C -0.4444(14) 0.4477(7) 0.0226(4) 0.0507(18) Uani 1 1 d . . .
H9A H -0.3604 0.3764 -0.0202 0.061 Uiso 1 1 calc R . .
H9B H -0.5808 0.3856 0.0419 0.061 Uiso 1 1 calc R . .
C6 C 0.4047(9) 0.6573(5) 0.5725(3) 0.0236(10) Uani 1 1 d . . .
H6A H 0.2530 0.5896 0.5627 0.028 Uiso 1 1 calc R . .
O1 O 0.3769(6) 0.7905(4) 0.3710(2) 0.0274(8) Uani 1 1 d . . .
O2 O 0.0966(7) 0.6323(4) 0.4157(2) 0.0340(9) Uani 1 1 d . . .
O3 O 0.7041(6) 0.5400(4) 0.7501(2) 0.0288(8) Uani 1 1 d . . .
O4 O 0.2953(7) 0.5163(4) 0.7092(3) 0.0381(9) Uani 1 1 d . . .
O5 O -0.2745(6) 0.6617(4) 0.1491(2) 0.0280(8) Uani 1 1 d . . .
O6 O -0.0891(7) 0.4527(4) 0.1226(2) 0.0387(9) Uani 1 1 d . . .
O1W O 0.2853(7) 0.7687(4) 0.1850(2) 0.0332(8) Uani 1 1 d . . .
H1WB H 0.3212 0.8641 0.2140 0.040 Uiso 1 1 d R . .
H1WA H 0.2070 0.7645 0.1356 0.040 Uiso 1 1 d R . .
O2W O -0.1471(7) 0.8532(4) 0.3240(2) 0.0308(8) Uani 1 1 d . . .
H2WA H -0.2898 0.8267 0.3367 0.046 Uiso 1 1 calc R . .
O3W O 0.8064(14) 0.1340(6) 0.0915(4) 0.094(2) Uani 1 1 d . . .
H3WB H 0.7190 0.2059 0.1124 0.113 Uiso 1 1 d R . .
H3WC H 0.8119 0.0687 0.1223 0.113 Uiso 1 1 d R . .
O4W O 0.2537(12) 0.9946(6) 0.0967(3) 0.0757(16) Uani 1 1 d . . .
H4WB H 0.3953 1.0485 0.0952 0.091 Uiso 1 1 d R . .
H4WA H 0.2286 0.9130 0.0534 0.091 Uiso 1 1 d R . .
H2WB H -0.092(13) 0.946(7) 0.350(4) 0.048(19) Uiso 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
Yb1 O4 2.217(4) 2_566 ?
Yb1 O3 2.239(3) 2_666 ?
Yb1 O2W 2.267(4) . ?
Yb1 O1W 2.288(3) . ?
Yb1 O6 2.389(4) . ?
Yb1 O2 2.412(3) . ?
Yb1 O5 2.422(3) . ?
Yb1 O1 2.449(3) . ?
Yb1 H1WB 2.6928 . ?
Yb1 H1WA 2.6943 . ?
C1 O2 1.254(6) . ?
C1 O1 1.280(6) . ?
C1 C2 1.502(6) . ?
C2 C6 1.385(7) . ?
C2 C3 1.388(7) . ?
C3 N1 1.336(6) . ?
C3 H3A 0.9300 . ?
N1 C4 1.336(6) . ?
C4 C5 1.396(7) . ?
C4 H4A 0.9300 . ?
C5 C6 1.379(7) . ?
C5 C7 1.495(6) . ?
C7 O4 1.249(6) . ?
C7 O3 1.248(6) . ?
C8 O6 1.257(6) . ?
C8 O5 1.266(6) . ?
C8 C9 1.506(8) . ?
C9 C9 1.472(10) 2_465 ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C6 H6A 0.9300 . ?
O3 Yb1 2.239(3) 2_666 ?
O4 Yb1 2.217(4) 2_566 ?
O1W H1WB 0.8501 . ?
O1W H1WA 0.8499 . ?
O2W H2WA 0.8200 . ?
O2W H2WB 0.83(6) . ?
O3W H3WB 0.8500 . ?
O3W H3WC 0.8499 . ?
O4W H4WB 0.8501 . ?
O4W H4WA 0.8500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 Yb1 O3 94.77(14) 2_566 2_666 ?
O4 Yb1 O2W 91.17(14) 2_566 . ?
O3 Yb1 O2W 158.79(13) 2_666 . ?
O4 Yb1 O1W 159.08(14) 2_566 . ?
O3 Yb1 O1W 89.48(12) 2_666 . ?
O2W Yb1 O1W 92.20(13) . . ?
O4 Yb1 O6 77.00(15) 2_566 . ?
O3 Yb1 O6 73.52(12) 2_666 . ?
O2W Yb1 O6 127.69(12) . . ?
O1W Yb1 O6 84.64(14) . . ?
O4 Yb1 O2 72.51(13) 2_566 . ?
O3 Yb1 O2 79.69(13) 2_666 . ?
O2W Yb1 O2 82.74(13) . . ?
O1W Yb1 O2 128.40(12) . . ?
O6 Yb1 O2 137.12(13) . . ?
O4 Yb1 O5 81.96(12) 2_566 . ?
O3 Yb1 O5 126.85(12) 2_666 . ?
O2W Yb1 O5 74.14(12) . . ?
O1W Yb1 O5 79.14(12) . . ?
O6 Yb1 O5 53.94(11) . . ?
O2 Yb1 O5 145.03(13) . . ?
O4 Yb1 O1 126.12(12) 2_566 . ?
O3 Yb1 O1 80.71(12) 2_666 . ?
O2W Yb1 O1 79.34(12) . . ?
O1W Yb1 O1 74.77(12) . . ?
O6 Yb1 O1 147.04(13) . . ?
O2 Yb1 O1 53.77(11) . . ?
O5 Yb1 O1 141.71(11) . . ?
O4 Yb1 H1WB 163.8 2_566 . ?
O3 Yb1 H1WB 100.0 2_666 . ?
O2W Yb1 H1WB 77.4 . . ?
O1W Yb1 H1WB 17.3 . . ?
O6 Yb1 H1WB 100.8 . . ?
O2 Yb1 H1WB 116.6 . . ?
O5 Yb1 H1WB 83.9 . . ?
O1 Yb1 H1WB 63.5 . . ?
O4 Yb1 H1WA 142.0 2_566 . ?
O3 Yb1 H1WA 96.4 2_666 . ?
O2W Yb1 H1WA 91.3 . . ?
O1W Yb1 H1WA 17.3 . . ?
O6 Yb1 H1WA 71.6 . . ?
O2 Yb1 H1WA 145.3 . . ?
O5 Yb1 H1WA 62.4 . . ?
O1 Yb1 H1WA 91.6 . . ?
H1WB Yb1 H1WA 29.6 . . ?
O2 C1 O1 120.4(4) . . ?
O2 C1 C2 119.6(4) . . ?
O1 C1 C2 119.9(4) . . ?
C6 C2 C3 118.3(4) . . ?
C6 C2 C1 120.3(4) . . ?
C3 C2 C1 121.3(4) . . ?
N1 C3 C2 123.3(5) . . ?
N1 C3 H3A 118.3 . . ?
C2 C3 H3A 118.3 . . ?
C4 N1 C3 117.7(4) . . ?
N1 C4 C5 122.9(5) . . ?
N1 C4 H4A 118.5 . . ?
C5 C4 H4A 118.5 . . ?
C6 C5 C4 118.4(4) . . ?
C6 C5 C7 121.2(4) . . ?
C4 C5 C7 120.4(4) . . ?
O4 C7 O3 124.7(4) . . ?
O4 C7 C5 116.0(4) . . ?
O3 C7 C5 119.2(4) . . ?
O6 C8 O5 119.7(5) . . ?
O6 C8 C9 119.0(5) . . ?
O5 C8 C9 121.1(5) . . ?
C9 C9 C8 115.9(6) 2_465 . ?
C9 C9 H9A 108.3 2_465 . ?
C8 C9 H9A 108.3 . . ?
C9 C9 H9B 108.3 2_465 . ?
C8 C9 H9B 108.3 . . ?
H9A C9 H9B 107.4 . . ?
C2 C6 C5 119.3(5) . . ?
C2 C6 H6A 120.4 . . ?
C5 C6 H6A 120.4 . . ?
C1 O1 Yb1 91.4(3) . . ?
C1 O2 Yb1 93.9(3) . . ?
C7 O3 Yb1 138.9(3) . 2_666 ?
C7 O4 Yb1 157.6(3) . 2_566 ?
C8 O5 Yb1 91.9(3) . . ?
C8 O6 Yb1 93.7(3) . . ?
Yb1 O1W H1WB 109.4 . . ?
Yb1 O1W H1WA 109.5 . . ?
H1WB O1W H1WA 108.2 . . ?
Yb1 O2W H2WA 109.5 . . ?
Yb1 O2W H2WB 135(5) . . ?
H2WA O2W H2WB 112.1 . . ?
H3WB O3W H3WC 113.5 . . ?
H4WB O4W H4WA 110.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C1 C2 C6 6.9(7) . . . . ?
O1 C1 C2 C6 -170.6(5) . . . . ?
O2 C1 C2 C3 -176.2(5) . . . . ?
O1 C1 C2 C3 6.3(7) . . . . ?
C6 C2 C3 N1 2.0(7) . . . . ?
C1 C2 C3 N1 -175.0(4) . . . . ?
C2 C3 N1 C4 1.8(8) . . . . ?
C3 N1 C4 C5 -3.9(8) . . . . ?
N1 C4 C5 C6 2.0(7) . . . . ?
N1 C4 C5 C7 -180.0(5) . . . . ?
C6 C5 C7 O4 -24.9(7) . . . . ?
C4 C5 C7 O4 157.1(5) . . . . ?
C6 C5 C7 O3 154.4(5) . . . . ?
C4 C5 C7 O3 -23.6(7) . . . . ?
O6 C8 C9 C9 -153.4(8) . . . 2_465 ?
O5 C8 C9 C9 29.8(12) . . . 2_465 ?
C3 C2 C6 C5 -3.8(7) . . . . ?
C1 C2 C6 C5 173.2(4) . . . . ?
C4 C5 C6 C2 1.9(7) . . . . ?
C7 C5 C6 C2 -176.1(4) . . . . ?
O2 C1 O1 Yb1 -7.3(5) . . . . ?
C2 C1 O1 Yb1 170.2(4) . . . . ?
O4 Yb1 O1 C1 9.2(3) 2_566 . . . ?
O3 Yb1 O1 C1 -79.9(3) 2_666 . . . ?
O2W Yb1 O1 C1 92.8(3) . . . . ?
O1W Yb1 O1 C1 -171.9(3) . . . . ?
O6 Yb1 O1 C1 -118.6(3) . . . . ?
O2 Yb1 O1 C1 4.0(3) . . . . ?
O5 Yb1 O1 C1 139.4(3) . . . . ?
O1 C1 O2 Yb1 7.4(5) . . . . ?
C2 C1 O2 Yb1 -170.1(4) . . . . ?
O4 Yb1 O2 C1 -179.7(3) 2_566 . . . ?
O3 Yb1 O2 C1 81.9(3) 2_666 . . . ?
O2W Yb1 O2 C1 -86.2(3) . . . . ?
O1W Yb1 O2 C1 0.8(4) . . . . ?
O6 Yb1 O2 C1 133.6(3) . . . . ?
O5 Yb1 O2 C1 -134.7(3) . . . . ?
O1 Yb1 O2 C1 -4.1(3) . . . . ?
O4 C7 O3 Yb1 88.7(7) . . . 2_666 ?
C5 C7 O3 Yb1 -90.5(6) . . . 2_666 ?
O3 C7 O4 Yb1 -17.1(13) . . . 2_566 ?
C5 C7 O4 Yb1 162.1(7) . . . 2_566 ?
O6 C8 O5 Yb1 -8.9(5) . . . . ?
C9 C8 O5 Yb1 167.9(5) . . . . ?
O4 Yb1 O5 C8 -74.7(3) 2_566 . . . ?
O3 Yb1 O5 C8 15.2(4) 2_666 . . . ?
O2W Yb1 O5 C8 -168.3(3) . . . . ?
O1W Yb1 O5 C8 96.3(3) . . . . ?
O6 Yb1 O5 C8 5.0(3) . . . . ?
O2 Yb1 O5 C8 -117.7(3) . . . . ?
O1 Yb1 O5 C8 143.8(3) . . . . ?
O5 C8 O6 Yb1 9.0(6) . . . . ?
C9 C8 O6 Yb1 -167.8(5) . . . . ?
O4 Yb1 O6 C8 84.4(3) 2_566 . . . ?
O3 Yb1 O6 C8 -176.5(4) 2_666 . . . ?
O2W Yb1 O6 C8 3.1(4) . . . . ?
O1W Yb1 O6 C8 -85.5(3) . . . . ?
O2 Yb1 O6 C8 129.8(3) . . . . ?
O5 Yb1 O6 C8 -5.0(3) . . . . ?
O1 Yb1 O6 C8 -136.5(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.976
_diffrn_reflns_theta_full        25.20
_diffrn_measured_fraction_theta_full 0.976
_refine_diff_density_max         1.101
_refine_diff_density_min         -1.191
_refine_diff_density_rms         0.130
_database_code_depnum_ccdc_archive 'CCDC 967482'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_CCDC

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H13 Lu N O10'
_chemical_formula_weight         470.17

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'
Lu Lu -0.4720 5.8584 '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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   p-1

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

_cell_length_a                   5.3400(8)
_cell_length_b                   8.9530(14)
_cell_length_c                   15.655(2)
_cell_angle_alpha                104.760(2)
_cell_angle_beta                 93.015(2)
_cell_angle_gamma                97.273(2)
_cell_volume                     715.11(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3440
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      27.53

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.184
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             450
_exptl_absorpt_coefficient_mu    6.952
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.206
_exptl_absorpt_correction_T_max  0.352
_exptl_absorpt_process_details   ?

_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3672
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_av_sigmaI/netI    0.0326
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.38
_diffrn_reflns_theta_max         25.20
_reflns_number_total             2517
_reflns_number_gt                2412
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL-XP (Bruker, 2004)'
_computing_publication_material  SHELXL-97

_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)+(0.0384P)²+4.9647P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2517
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0284
_refine_ls_R_factor_gt           0.0271
_refine_ls_wR_factor_ref         0.0783
_refine_ls_wR_factor_gt          0.0775
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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
Lu1 Lu 0.97009(5) 0.36274(3) 0.237090(17) 0.01991(11) Uani 1 1 d . . .
C1 C 0.6979(13) 0.2773(8) 0.0708(4) 0.0257(14) Uani 1 1 d . . .
C2 C 0.5348(12) 0.2517(8) -0.0134(4) 0.0237(14) Uani 1 1 d . . .
C3 C 0.3160(13) 0.1472(7) -0.0340(4) 0.0232(13) Uani 1 1 d . . .
H3A H 0.2789 0.0840 0.0038 0.028 Uiso 1 1 calc R . .
C4 C 0.2045(12) 0.2214(8) -0.1604(5) 0.0247(14) Uani 1 1 d . . .
H4A H 0.0927 0.2124 -0.2096 0.030 Uiso 1 1 calc R . .
C5 C 0.4258(12) 0.3301(8) -0.1446(4) 0.0225(13) Uani 1 1 d . . .
C6 C 0.5947(12) 0.3430(7) -0.0724(4) 0.0221(13) Uani 1 1 d . . .
H6A H 0.7461 0.4113 -0.0629 0.026 Uiso 1 1 calc R . .
C7 C 0.4791(13) 0.4325(7) -0.2055(4) 0.0244(14) Uani 1 1 d . . .
C8 C 1.2592(14) 0.4745(9) 0.3981(4) 0.0297(15) Uani 1 1 d . . .
C9 C 1.4466(19) 0.5517(10) 0.4789(6) 0.052(2) Uani 1 1 d . . .
H9A H 1.5837 0.6156 0.4608 0.063 Uiso 1 1 calc R . .
H9B H 1.3612 0.6210 0.5221 0.063 Uiso 1 1 calc R . .
N1 N 0.1497(11) 0.1293(7) -0.1056(4) 0.0295(13) Uani 1 1 d . . .
O1 O 0.6234(9) 0.2100(6) 0.1294(3) 0.0262(10) Uani 1 1 d . . .
O2 O 0.9030(9) 0.3671(6) 0.0845(3) 0.0335(12) Uani 1 1 d . . .
O3 O 0.2936(9) 0.4594(6) -0.2506(3) 0.0303(11) Uani 1 1 d . . .
O4 O 0.7046(9) 0.4854(7) -0.2082(4) 0.0378(13) Uani 1 1 d . . .
O5 O 1.2747(9) 0.3391(6) 0.3501(3) 0.0272(10) Uani 1 1 d . . .
O6 O 1.0906(10) 0.5473(6) 0.3767(3) 0.0396(13) Uani 1 1 d . . .
O1W O 0.7192(9) 0.2325(6) 0.3151(3) 0.0324(11) Uani 1 1 d . . .
H1WA H 0.7975 0.2375 0.3647 0.039 Uiso 1 1 d R . .
H1WB H 0.6839 0.1369 0.2866 0.039 Uiso 1 1 d R . .
O2W O 1.1464(9) 0.1471(6) 0.1760(3) 0.0310(11) Uani 1 1 d . . .
H2WA H 1.0554 0.0931 0.1296 0.037 Uiso 1 1 d R . .
H2WB H 1.1531 0.0916 0.2125 0.037 Uiso 1 1 d R . .
O3W O 0.7470(17) 0.0067(8) 0.4047(4) 0.075(2) Uani 1 1 d G . .
H3WA H 0.6048 -0.0478 0.4050 0.091 Uiso 1 1 d R . .
H3WB H 0.7721 0.0858 0.4494 0.091 Uiso 1 1 d R . .
O4W O 0.8017(19) 0.1340(9) 0.5946(4) 0.086(3) Uani 1 1 d G . .
H4WA H 0.9177 0.0772 0.5949 0.103 Uiso 1 1 d R . .
H4WB H 0.8268 0.2131 0.6393 0.103 Uiso 1 1 d R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Lu1 O4 2.207(5) 2_765 ?
Lu1 O3 2.234(5) 2_665 ?
Lu1 O2W 2.267(5) . ?
Lu1 O1W 2.269(5) . ?
Lu1 O6 2.380(5) . ?
Lu1 O2 2.407(5) . ?
Lu1 O5 2.408(4) . ?
Lu1 O1 2.449(5) . ?
C1 O2 1.247(8) . ?
C1 O1 1.274(8) . ?
C1 C2 1.491(9) . ?
C2 C3 1.369(9) . ?
C2 C6 1.405(9) . ?
C3 N1 1.355(9) . ?
C3 H3A 0.9300 . ?
C4 N1 1.352(9) . ?
C4 C5 1.400(9) . ?
C4 H4A 0.9300 . ?
C5 C6 1.381(9) . ?
C5 C7 1.495(9) . ?
C6 H6A 0.9300 . ?
C7 O4 1.244(8) . ?
C7 O3 1.270(8) . ?
C8 O6 1.255(9) . ?
C8 O5 1.267(9) . ?
C8 C9 1.525(10) . ?
C9 C9 1.424(17) 2_866 ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
O3 Lu1 2.234(5) 2_665 ?
O4 Lu1 2.207(5) 2_765 ?
O1W H1WA 0.8500 . ?
O1W H1WB 0.8500 . ?
O2W H2WA 0.8500 . ?
O2W H2WB 0.8500 . ?
O3W H3WA 0.8500 . ?
O3W H3WB 0.8501 . ?
O4W H4WA 0.8500 . ?
O4W H4WB 0.8499 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 Lu1 O3 94.97(19) 2_765 2_665 ?
O4 Lu1 O2W 90.9(2) 2_765 . ?
O3 Lu1 O2W 158.86(18) 2_665 . ?
O4 Lu1 O1W 159.13(19) 2_765 . ?
O3 Lu1 O1W 89.75(17) 2_665 . ?
O2W Lu1 O1W 91.98(18) . . ?
O4 Lu1 O6 77.3(2) 2_765 . ?
O3 Lu1 O6 73.28(17) 2_665 . ?
O2W Lu1 O6 127.86(17) . . ?
O1W Lu1 O6 84.6(2) . . ?
O4 Lu1 O2 72.42(17) 2_765 . ?
O3 Lu1 O2 79.99(18) 2_665 . ?
O2W Lu1 O2 82.47(19) . . ?
O1W Lu1 O2 128.45(17) . . ?
O6 Lu1 O2 137.29(19) . . ?
O4 Lu1 O5 81.94(17) 2_765 . ?
O3 Lu1 O5 126.68(17) 2_665 . ?
O2W Lu1 O5 74.24(17) . . ?
O1W Lu1 O5 78.96(17) . . ?
O6 Lu1 O5 54.00(16) . . ?
O2 Lu1 O5 144.93(17) . . ?
O4 Lu1 O1 125.76(17) 2_765 . ?
O3 Lu1 O1 80.99(17) 2_665 . ?
O2W Lu1 O1 79.12(16) . . ?
O1W Lu1 O1 75.05(17) . . ?
O6 Lu1 O1 147.16(17) . . ?
O2 Lu1 O1 53.51(15) . . ?
O5 Lu1 O1 141.78(16) . . ?
O2 C1 O1 120.3(6) . . ?
O2 C1 C2 120.1(6) . . ?
O1 C1 C2 119.5(6) . . ?
C3 C2 C6 117.4(6) . . ?
C3 C2 C1 122.4(6) . . ?
C6 C2 C1 120.1(6) . . ?
N1 C3 C2 124.7(6) . . ?
N1 C3 H3A 117.6 . . ?
C2 C3 H3A 117.6 . . ?
N1 C4 C5 121.5(6) . . ?
N1 C4 H4A 119.3 . . ?
C5 C4 H4A 119.3 . . ?
C6 C5 C4 119.7(6) . . ?
C6 C5 C7 120.0(6) . . ?
C4 C5 C7 120.3(6) . . ?
C5 C6 C2 119.1(6) . . ?
C5 C6 H6A 120.5 . . ?
C2 C6 H6A 120.5 . . ?
O4 C7 O3 124.5(6) . . ?
O4 C7 C5 117.1(6) . . ?
O3 C7 C5 118.4(6) . . ?
O6 C8 O5 119.0(6) . . ?
O6 C8 C9 119.7(7) . . ?
O5 C8 C9 121.2(6) . . ?
C9 C9 C8 115.7(9) 2_866 . ?
C9 C9 H9A 108.3 2_866 . ?
C8 C9 H9A 108.3 . . ?
C9 C9 H9B 108.3 2_866 . ?
C8 C9 H9B 108.3 . . ?
H9A C9 H9B 107.4 . . ?
C4 N1 C3 117.4(6) . . ?
C1 O1 Lu1 91.5(4) . . ?
C1 O2 Lu1 94.1(4) . . ?
C7 O3 Lu1 137.9(5) . 2_665 ?
C7 O4 Lu1 158.0(5) . 2_765 ?
C8 O5 Lu1 92.3(4) . . ?
C8 O6 Lu1 93.9(4) . . ?
Lu1 O1W H1WA 109.7 . . ?
Lu1 O1W H1WB 109.6 . . ?
H1WA O1W H1WB 108.2 . . ?
Lu1 O2W H2WA 109.6 . . ?
Lu1 O2W H2WB 109.7 . . ?
H2WA O2W H2WB 108.2 . . ?
H3WA O3W H3WB 110.6 . . ?
H4WA O4W H4WB 110.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C1 C2 C3 175.9(7) . . . . ?
O1 C1 C2 C3 -5.9(10) . . . . ?
O2 C1 C2 C6 -8.2(10) . . . . ?
O1 C1 C2 C6 170.1(6) . . . . ?
C6 C2 C3 N1 -2.2(10) . . . . ?
C1 C2 C3 N1 173.8(6) . . . . ?
N1 C4 C5 C6 0.8(10) . . . . ?
N1 C4 C5 C7 -178.9(6) . . . . ?
C4 C5 C6 C2 -3.0(10) . . . . ?
C7 C5 C6 C2 176.7(6) . . . . ?
C3 C2 C6 C5 3.7(9) . . . . ?
C1 C2 C6 C5 -172.5(6) . . . . ?
C6 C5 C7 O4 24.4(10) . . . . ?
C4 C5 C7 O4 -155.9(7) . . . . ?
C6 C5 C7 O3 -155.7(6) . . . . ?
C4 C5 C7 O3 24.0(9) . . . . ?
O6 C8 C9 C9 153.7(11) . . . 2_866 ?
O5 C8 C9 C9 -28.4(17) . . . 2_866 ?
C5 C4 N1 C3 0.7(10) . . . . ?
C2 C3 N1 C4 0.0(10) . . . . ?
O2 C1 O1 Lu1 7.5(7) . . . . ?
C2 C1 O1 Lu1 -170.8(5) . . . . ?
O4 Lu1 O1 C1 -9.7(5) 2_765 . . . ?
O3 Lu1 O1 C1 80.0(4) 2_665 . . . ?
O2W Lu1 O1 C1 -92.8(4) . . . . ?
O1W Lu1 O1 C1 172.2(4) . . . . ?
O6 Lu1 O1 C1 118.5(4) . . . . ?
O2 Lu1 O1 C1 -4.2(4) . . . . ?
O5 Lu1 O1 C1 -139.1(4) . . . . ?
O1 C1 O2 Lu1 -7.7(7) . . . . ?
C2 C1 O2 Lu1 170.6(5) . . . . ?
O4 Lu1 O2 C1 179.6(5) 2_765 . . . ?
O3 Lu1 O2 C1 -81.9(4) 2_665 . . . ?
O2W Lu1 O2 C1 86.3(4) . . . . ?
O1W Lu1 O2 C1 -0.3(5) . . . . ?
O6 Lu1 O2 C1 -133.4(4) . . . . ?
O5 Lu1 O2 C1 134.6(4) . . . . ?
O1 Lu1 O2 C1 4.3(4) . . . . ?
O4 C7 O3 Lu1 -88.7(9) . . . 2_665 ?
C5 C7 O3 Lu1 91.4(8) . . . 2_665 ?
O3 C7 O4 Lu1 15.9(19) . . . 2_765 ?
C5 C7 O4 Lu1 -164.2(11) . . . 2_765 ?
O6 C8 O5 Lu1 8.7(7) . . . . ?
C9 C8 O5 Lu1 -169.2(7) . . . . ?
O4 Lu1 O5 C8 75.2(4) 2_765 . . . ?
O3 Lu1 O5 C8 -15.0(5) 2_665 . . . ?
O2W Lu1 O5 C8 168.4(4) . . . . ?
O1W Lu1 O5 C8 -96.3(4) . . . . ?
O6 Lu1 O5 C8 -5.0(4) . . . . ?
O2 Lu1 O5 C8 118.1(5) . . . . ?
O1 Lu1 O5 C8 -144.1(4) . . . . ?
O5 C8 O6 Lu1 -8.8(7) . . . . ?
C9 C8 O6 Lu1 169.1(7) . . . . ?
O4 Lu1 O6 C8 -84.2(5) 2_765 . . . ?
O3 Lu1 O6 C8 176.6(5) 2_665 . . . ?
O2W Lu1 O6 C8 -3.1(6) . . . . ?
O1W Lu1 O6 C8 85.3(5) . . . . ?
O2 Lu1 O6 C8 -129.8(5) . . . . ?
O5 Lu1 O6 C8 5.0(4) . . . . ?
O1 Lu1 O6 C8 136.7(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.972
_diffrn_reflns_theta_full        25.20
_diffrn_measured_fraction_theta_full 0.972
_refine_diff_density_max         0.960
_refine_diff_density_min         -1.473
_refine_diff_density_rms         0.153
_database_code_depnum_ccdc_archive 'CCDC 967483'
