# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_228-7la
_database_code_depnum_ccdc_archive 'CCDC 1434380'
_audit_update_record             
;
2015-10-30 deposited with the CCDC.
2016-02-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H17 F3 La N3 O10'
_chemical_formula_weight         631.26

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
La La -0.2871 2.4523 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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                   6.8378(4)
_cell_length_b                   12.9909(8)
_cell_length_c                   13.6543(8)
_cell_angle_alpha                74.892(5)
_cell_angle_beta                 77.728(5)
_cell_angle_gamma                77.116(5)
_cell_volume                     1126.02(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.862
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             620
_exptl_absorpt_coefficient_mu    1.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6372
_exptl_absorpt_correction_T_max  0.6927
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71000
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APE-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7188
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_av_sigmaI/netI    0.0884
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.30
_diffrn_reflns_theta_max         25.04
_reflns_number_total             3994
_reflns_number_gt                3343
_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    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0000P)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         3994
_refine_ls_number_parameters     327
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0423
_refine_ls_wR_factor_ref         0.0707
_refine_ls_wR_factor_gt          0.0618
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_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
La1 La 0.17460(5) 0.61646(2) 0.62610(2) 0.02266(10) Uani 1 1 d . . .
N1 N -0.0247(7) 1.0464(4) 0.2569(4) 0.0394(12) Uani 1 1 d . . .
N2 N 0.3747(8) 0.3321(4) 1.0801(4) 0.0463(14) Uani 1 1 d . . .
N3 N 0.4968(7) 0.0540(4) 0.6958(4) 0.0407(13) Uani 1 1 d . . .
O1 O 0.1261(6) 0.6716(3) 0.4227(3) 0.0392(10) Uani 1 1 d . . .
O2 O -0.0071(6) 0.7937(3) 0.5144(3) 0.0431(11) Uani 1 1 d . . .
O3 O 0.4684(6) 0.5356(3) 0.7330(3) 0.0397(10) Uani 1 1 d . . .
O4 O 0.1601(6) 0.5161(3) 0.8156(3) 0.0400(10) Uani 1 1 d . . .
O5 O 0.2979(6) 0.4359(3) 0.5946(3) 0.0355(10) Uani 1 1 d . . .
O6 O 0.5053(5) 0.3446(3) 0.4844(3) 0.0331(9) Uani 1 1 d . . .
O7 O -0.1204(6) 0.5198(3) 0.6396(3) 0.0448(11) Uani 1 1 d . . .
H1W H -0.0806 0.4694 0.6068 0.067 Uiso 1 1 d R . .
H2W H -0.2165 0.5653 0.6136 0.067 Uiso 1 1 d R . .
O8 O -0.1391(6) 0.7066(3) 0.7292(3) 0.0452(11) Uani 1 1 d . . .
H4W H -0.1271 0.7710 0.7280 0.068 Uiso 1 1 d R . .
H3W H -0.1513 0.6702 0.7914 0.068 Uiso 1 1 d R . .
O9 O 0.2690(6) 0.7697(3) 0.6791(3) 0.0437(11) Uani 1 1 d . . .
H5W H 0.1623 0.8182 0.6894 0.066 Uiso 1 1 d R . .
H6W H 0.3570 0.7994 0.6310 0.066 Uiso 1 1 d R . .
O10 O 0.6056(8) 0.8702(4) 0.6145(4) 0.0529(13) Uani 1 1 d . . .
F1 F 0.2071(6) 0.9047(3) 0.0583(2) 0.0733(13) Uani 1 1 d . . .
F2 F 0.9117(6) 0.2991(3) 0.9927(3) 0.0700(11) Uani 1 1 d . . .
F3 F 0.2763(7) 0.1472(3) 0.9253(3) 0.0800(14) Uani 1 1 d . . .
C1 C 0.0556(8) 0.7668(4) 0.4280(4) 0.0280(13) Uani 1 1 d . . .
C2 C 0.0518(8) 0.8553(4) 0.3327(4) 0.0255(12) Uani 1 1 d . . .
C3 C 0.1297(8) 0.8344(4) 0.2370(4) 0.0346(14) Uani 1 1 d . . .
H3 H 0.1804 0.7640 0.2285 0.042 Uiso 1 1 calc R . .
C4 C 0.1296(9) 0.9211(5) 0.1546(4) 0.0394(16) Uani 1 1 d . . .
C5 C 0.0523(9) 1.0248(5) 0.1647(4) 0.0421(16) Uani 1 1 d . . .
H5 H 0.0535 1.0812 0.1065 0.051 Uiso 1 1 calc R . .
C6 C -0.0231(8) 0.9624(4) 0.3384(4) 0.0335(14) Uani 1 1 d . . .
H6 H -0.0756 0.9768 0.4031 0.040 Uiso 1 1 calc R . .
C7 C 0.3505(9) 0.4988(4) 0.8124(4) 0.0304(13) Uani 1 1 d . . .
C8 C 0.4388(9) 0.4297(4) 0.9049(4) 0.0289(13) Uani 1 1 d . . .
C9 C 0.6444(9) 0.3985(4) 0.9029(4) 0.0336(14) Uani 1 1 d . . .
H9 H 0.7360 0.4208 0.8443 0.040 Uiso 1 1 calc R . .
C10 C 0.7103(9) 0.3333(5) 0.9904(5) 0.0402(15) Uani 1 1 d . . .
C11 C 0.5757(10) 0.3016(5) 1.0767(4) 0.0448(16) Uani 1 1 d . . .
H11 H 0.6253 0.2576 1.1349 0.054 Uiso 1 1 calc R . .
C12 C 0.3106(9) 0.3942(5) 0.9947(4) 0.0388(15) Uani 1 1 d . . .
H12 H 0.1712 0.4151 0.9955 0.047 Uiso 1 1 calc R . .
C13 C 0.4015(8) 0.3514(4) 0.5704(4) 0.0248(12) Uani 1 1 d . . .
C14 C 0.4038(8) 0.2481(4) 0.6536(4) 0.0263(13) Uani 1 1 d . . .
C15 C 0.3265(8) 0.2489(4) 0.7555(4) 0.0347(14) Uani 1 1 d . . .
H15 H 0.2664 0.3131 0.7763 0.042 Uiso 1 1 calc R . .
C16 C 0.3425(10) 0.1511(5) 0.8245(5) 0.0451(17) Uani 1 1 d . . .
C17 C 0.4264(9) 0.0559(5) 0.7940(5) 0.0481(17) Uani 1 1 d . . .
H17 H 0.4342 -0.0090 0.8432 0.058 Uiso 1 1 calc R . .
C18 C 0.4865(8) 0.1482(4) 0.6282(4) 0.0318(14) Uani 1 1 d . . .
H18 H 0.5376 0.1478 0.5595 0.038 Uiso 1 1 calc R . .
H7W H 0.586(12) 0.925(6) 0.641(6) 0.11(4) Uiso 1 1 d . . .
H8W H 0.696(10) 0.876(5) 0.566(5) 0.05(2) 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
La1 O5 2.426(3) . ?
La1 O6 2.453(3) 2_666 ?
La1 O8 2.532(3) . ?
La1 O9 2.535(3) . ?
La1 O7 2.556(3) . ?
La1 O4 2.569(3) . ?
La1 O3 2.603(4) . ?
La1 O2 2.621(4) . ?
La1 O1 2.754(4) . ?
N1 C5 1.333(6) . ?
N1 C6 1.340(6) . ?
N2 C12 1.331(7) . ?
N2 C11 1.337(7) . ?
N3 C18 1.325(6) . ?
N3 C17 1.329(7) . ?
O1 C1 1.239(6) . ?
O2 C1 1.278(5) . ?
O3 C7 1.259(6) . ?
O4 C7 1.264(6) . ?
O5 C13 1.249(6) . ?
O6 C13 1.250(5) . ?
O6 La1 2.453(3) 2_666 ?
O7 H1W 0.8508 . ?
O7 H2W 0.8509 . ?
O8 H4W 0.8550 . ?
O8 H3W 0.8549 . ?
O9 H5W 0.8643 . ?
O9 H6W 0.8640 . ?
O10 H7W 0.85(7) . ?
O10 H8W 0.81(6) . ?
F1 C4 1.362(5) . ?
F2 C10 1.354(6) . ?
F3 C16 1.346(6) . ?
C1 C2 1.495(7) . ?
C2 C3 1.375(6) . ?
C2 C6 1.388(7) . ?
C3 C4 1.369(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.365(8) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.502(7) . ?
C8 C9 1.369(7) . ?
C8 C12 1.383(7) . ?
C9 C10 1.371(8) . ?
C9 H9 0.9300 . ?
C10 C11 1.364(7) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.515(7) . ?
C14 C15 1.382(6) . ?
C14 C18 1.395(7) . ?
C15 C16 1.368(8) . ?
C15 H15 0.9300 . ?
C16 C17 1.372(8) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O5 La1 O6 83.69(11) . 2_666 ?
O5 La1 O8 135.25(11) . . ?
O6 La1 O8 141.06(11) 2_666 . ?
O5 La1 O9 144.29(13) . . ?
O6 La1 O9 73.03(11) 2_666 . ?
O8 La1 O9 71.88(12) . . ?
O5 La1 O7 68.92(13) . . ?
O6 La1 O7 141.69(11) 2_666 . ?
O8 La1 O7 71.08(12) . . ?
O9 La1 O7 142.96(12) . . ?
O5 La1 O4 83.51(12) . . ?
O6 La1 O4 122.00(12) 2_666 . ?
O8 La1 O4 71.83(12) . . ?
O9 La1 O4 86.30(12) . . ?
O7 La1 O4 82.08(12) . . ?
O5 La1 O3 75.48(12) . . ?
O6 La1 O3 71.58(12) 2_666 . ?
O8 La1 O3 111.93(12) . . ?
O9 La1 O3 71.70(12) . . ?
O7 La1 O3 123.07(12) . . ?
O4 La1 O3 50.44(11) . . ?
O5 La1 O2 131.28(12) . . ?
O6 La1 O2 87.22(12) 2_666 . ?
O8 La1 O2 67.93(11) . . ?
O9 La1 O2 75.16(12) . . ?
O7 La1 O2 91.20(13) . . ?
O4 La1 O2 139.17(12) . . ?
O3 La1 O2 144.58(11) . . ?
O5 La1 O1 84.04(11) . . ?
O6 La1 O1 70.05(11) 2_666 . ?
O8 La1 O1 108.44(12) . . ?
O9 La1 O1 111.70(11) . . ?
O7 La1 O1 80.60(11) . . ?
O4 La1 O1 161.42(10) . . ?
O3 La1 O1 138.04(11) . . ?
O2 La1 O1 48.15(11) . . ?
C5 N1 C6 117.3(5) . . ?
C12 N2 C11 117.0(5) . . ?
C18 N3 C17 117.4(5) . . ?
C1 O1 La1 91.2(3) . . ?
C1 O2 La1 96.6(3) . . ?
C7 O3 La1 93.1(3) . . ?
C7 O4 La1 94.5(3) . . ?
C13 O5 La1 165.9(3) . . ?
C13 O6 La1 142.2(3) . 2_666 ?
La1 O7 H1W 109.5 . . ?
La1 O7 H2W 109.0 . . ?
H1W O7 H2W 109.5 . . ?
La1 O8 H4W 109.9 . . ?
La1 O8 H3W 108.8 . . ?
H4W O8 H3W 109.1 . . ?
La1 O9 H5W 110.1 . . ?
La1 O9 H6W 109.7 . . ?
H5W O9 H6W 108.8 . . ?
H7W O10 H8W 109(6) . . ?
O1 C1 O2 121.6(5) . . ?
O1 C1 C2 120.6(5) . . ?
O2 C1 C2 117.7(5) . . ?
C3 C2 C6 117.7(5) . . ?
C3 C2 C1 121.5(5) . . ?
C6 C2 C1 120.8(5) . . ?
C4 C3 C2 117.4(5) . . ?
C4 C3 H3 121.3 . . ?
C2 C3 H3 121.3 . . ?
F1 C4 C5 117.9(5) . . ?
F1 C4 C3 119.6(5) . . ?
C5 C4 C3 122.4(5) . . ?
N1 C5 C4 120.9(5) . . ?
N1 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
N1 C6 C2 124.3(5) . . ?
N1 C6 H6 117.9 . . ?
C2 C6 H6 117.9 . . ?
O3 C7 O4 121.8(5) . . ?
O3 C7 C8 119.1(5) . . ?
O4 C7 C8 119.0(5) . . ?
C9 C8 C12 118.3(5) . . ?
C9 C8 C7 122.0(5) . . ?
C12 C8 C7 119.7(5) . . ?
C8 C9 C10 117.7(5) . . ?
C8 C9 H9 121.2 . . ?
C10 C9 H9 121.2 . . ?
F2 C10 C11 118.6(6) . . ?
F2 C10 C9 120.3(5) . . ?
C11 C10 C9 121.1(6) . . ?
N2 C11 C10 121.9(6) . . ?
N2 C11 H11 119.0 . . ?
C10 C11 H11 119.0 . . ?
N2 C12 C8 124.0(6) . . ?
N2 C12 H12 118.0 . . ?
C8 C12 H12 118.0 . . ?
O5 C13 O6 125.9(5) . . ?
O5 C13 C14 116.9(4) . . ?
O6 C13 C14 117.2(5) . . ?
C15 C14 C18 118.1(5) . . ?
C15 C14 C13 122.0(5) . . ?
C18 C14 C13 119.9(5) . . ?
C16 C15 C14 116.9(5) . . ?
C16 C15 H15 121.5 . . ?
C14 C15 H15 121.5 . . ?
F3 C16 C15 119.7(5) . . ?
F3 C16 C17 118.5(6) . . ?
C15 C16 C17 121.8(5) . . ?
N3 C17 C16 121.7(6) . . ?
N3 C17 H17 119.2 . . ?
C16 C17 H17 119.2 . . ?
N3 C18 C14 124.1(5) . . ?
N3 C18 H18 117.9 . . ?
C14 C18 H18 117.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O5 La1 O1 C1 178.5(3) . . . . ?
O6 La1 O1 C1 -96.0(3) 2_666 . . . ?
O8 La1 O1 C1 42.7(3) . . . . ?
O9 La1 O1 C1 -34.6(3) . . . . ?
O7 La1 O1 C1 109.0(3) . . . . ?
O4 La1 O1 C1 130.4(4) . . . . ?
O3 La1 O1 C1 -121.0(3) . . . . ?
O2 La1 O1 C1 8.8(3) . . . . ?
O5 La1 O2 C1 -22.2(4) . . . . ?
O6 La1 O2 C1 56.9(3) 2_666 . . . ?
O8 La1 O2 C1 -153.8(3) . . . . ?
O9 La1 O2 C1 130.1(3) . . . . ?
O7 La1 O2 C1 -84.8(3) . . . . ?
O4 La1 O2 C1 -164.1(3) . . . . ?
O3 La1 O2 C1 109.0(3) . . . . ?
O1 La1 O2 C1 -8.6(3) . . . . ?
O5 La1 O3 C7 -91.4(3) . . . . ?
O6 La1 O3 C7 -179.5(3) 2_666 . . . ?
O8 La1 O3 C7 41.9(3) . . . . ?
O9 La1 O3 C7 102.8(3) . . . . ?
O7 La1 O3 C7 -39.2(3) . . . . ?
O4 La1 O3 C7 2.2(3) . . . . ?
O2 La1 O3 C7 124.3(3) . . . . ?
O1 La1 O3 C7 -154.8(3) . . . . ?
O5 La1 O4 C7 74.3(3) . . . . ?
O6 La1 O4 C7 -4.0(3) 2_666 . . . ?
O8 La1 O4 C7 -143.5(3) . . . . ?
O9 La1 O4 C7 -71.4(3) . . . . ?
O7 La1 O4 C7 143.9(3) . . . . ?
O3 La1 O4 C7 -2.2(3) . . . . ?
O2 La1 O4 C7 -133.5(3) . . . . ?
O1 La1 O4 C7 122.6(4) . . . . ?
O6 La1 O5 C13 13.9(15) 2_666 . . . ?
O8 La1 O5 C13 -165.3(14) . . . . ?
O9 La1 O5 C13 -35.0(16) . . . . ?
O7 La1 O5 C13 166.6(15) . . . . ?
O4 La1 O5 C13 -109.4(15) . . . . ?
O3 La1 O5 C13 -58.7(15) . . . . ?
O2 La1 O5 C13 94.6(15) . . . . ?
O1 La1 O5 C13 84.4(15) . . . . ?
La1 O1 C1 O2 -15.9(5) . . . . ?
La1 O1 C1 C2 160.7(4) . . . . ?
La1 O2 C1 O1 16.9(6) . . . . ?
La1 O2 C1 C2 -159.9(4) . . . . ?
O1 C1 C2 C3 -1.4(8) . . . . ?
O2 C1 C2 C3 175.4(5) . . . . ?
O1 C1 C2 C6 -178.6(5) . . . . ?
O2 C1 C2 C6 -1.9(8) . . . . ?
C6 C2 C3 C4 0.8(8) . . . . ?
C1 C2 C3 C4 -176.6(5) . . . . ?
C2 C3 C4 F1 179.3(5) . . . . ?
C2 C3 C4 C5 -1.3(9) . . . . ?
C6 N1 C5 C4 0.0(9) . . . . ?
F1 C4 C5 N1 -179.6(5) . . . . ?
C3 C4 C5 N1 1.0(10) . . . . ?
C5 N1 C6 C2 -0.5(9) . . . . ?
C3 C2 C6 N1 0.1(8) . . . . ?
C1 C2 C6 N1 177.5(5) . . . . ?
La1 O3 C7 O4 -4.0(5) . . . . ?
La1 O3 C7 C8 174.3(4) . . . . ?
La1 O4 C7 O3 4.1(5) . . . . ?
La1 O4 C7 C8 -174.2(4) . . . . ?
O3 C7 C8 C9 -5.2(7) . . . . ?
O4 C7 C8 C9 173.1(5) . . . . ?
O3 C7 C8 C12 176.0(4) . . . . ?
O4 C7 C8 C12 -5.7(7) . . . . ?
C12 C8 C9 C10 0.4(8) . . . . ?
C7 C8 C9 C10 -178.5(5) . . . . ?
C8 C9 C10 F2 179.4(5) . . . . ?
C8 C9 C10 C11 -0.8(8) . . . . ?
C12 N2 C11 C10 0.6(9) . . . . ?
F2 C10 C11 N2 -179.9(5) . . . . ?
C9 C10 C11 N2 0.3(9) . . . . ?
C11 N2 C12 C8 -1.1(8) . . . . ?
C9 C8 C12 N2 0.5(8) . . . . ?
C7 C8 C12 N2 179.4(5) . . . . ?
La1 O5 C13 O6 -53.8(18) . . . . ?
La1 O5 C13 C14 125.2(13) . . . . ?
La1 O6 C13 O5 75.7(8) 2_666 . . . ?
La1 O6 C13 C14 -103.4(5) 2_666 . . . ?
O5 C13 C14 C15 -11.3(8) . . . . ?
O6 C13 C14 C15 167.9(5) . . . . ?
O5 C13 C14 C18 169.0(5) . . . . ?
O6 C13 C14 C18 -11.8(7) . . . . ?
C18 C14 C15 C16 1.8(8) . . . . ?
C13 C14 C15 C16 -178.0(5) . . . . ?
C14 C15 C16 F3 177.7(5) . . . . ?
C14 C15 C16 C17 -1.7(9) . . . . ?
C18 N3 C17 C16 1.2(9) . . . . ?
F3 C16 C17 N3 -179.3(5) . . . . ?
C15 C16 C17 N3 0.1(10) . . . . ?
C17 N3 C18 C14 -1.1(8) . . . . ?
C15 C14 C18 N3 -0.4(8) . . . . ?
C13 C14 C18 N3 179.3(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O7 H1W O1 0.85 2.08 2.839(5) 149.1 2_566
O8 H3W N2 0.85 2.07 2.743(5) 135.7 2_567
O9 H5W N1 0.86 2.04 2.820(6) 149.8 2_576
O9 H6W O10 0.86 2.05 2.767(6) 139.6 .
O10 H7W N3 0.85(7) 1.93(7) 2.780(6) 170(8) 1_565
O10 H8W O2 0.81(6) 2.14(6) 2.804(6) 139(6) 1_655

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.04
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.752
_refine_diff_density_min         -0.608
_refine_diff_density_rms         0.130
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_gu205_10pr
_database_code_depnum_ccdc_archive 'CCDC 1434381'
_audit_update_record             
;
2015-10-30 deposited with the CCDC.
2016-02-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H17 F3 N3 O10 Pr'
_chemical_formula_weight         633.26

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   6.8156(8)
_cell_length_b                   12.9140(15)
_cell_length_c                   13.6372(13)
_cell_angle_alpha                74.710(9)
_cell_angle_beta                 77.652(9)
_cell_angle_gamma                76.938(10)
_cell_volume                     1112.6(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.890
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_absorpt_coefficient_mu    2.275
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6001
_exptl_absorpt_correction_T_max  0.6590
_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 APE-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7838
_diffrn_reflns_av_R_equivalents  0.0521
_diffrn_reflns_av_sigmaI/netI    0.0826
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.34
_diffrn_reflns_theta_max         25.05
_reflns_number_total             3930
_reflns_number_gt                3345
_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    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0264P)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         3930
_refine_ls_number_parameters     322
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_ref         0.0860
_refine_ls_wR_factor_gt          0.0802
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_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
Pr1 Pr 0.17691(5) 0.11586(2) 0.12597(2) 0.01987(11) Uani 1 1 d . . .
O1 O 0.4707(6) 0.0348(3) 0.2318(3) 0.0347(10) Uani 1 1 d . . .
O2 O 0.1603(6) 0.0159(3) 0.3129(3) 0.0363(11) Uani 1 1 d . . .
O3 O 0.1273(7) 0.1697(3) -0.0759(3) 0.0377(11) Uani 1 1 d . . .
O4 O -0.0025(7) 0.2922(3) 0.0162(3) 0.0413(11) Uani 1 1 d . . .
O5 O 0.4924(6) 0.1554(3) 0.0164(3) 0.0293(9) Uani 1 1 d . . .
O6 O 0.6996(6) 0.0623(3) -0.0934(3) 0.0310(10) Uani 1 1 d . . .
O7 O -0.1283(6) 0.2049(3) 0.2294(3) 0.0386(11) Uani 1 1 d . . .
H1W H -0.1697 0.1586 0.2867 0.058 Uiso 1 1 d R . .
H2W H -0.2306 0.2291 0.1941 0.058 Uiso 1 1 d R . .
O8 O -0.1147(6) 0.0236(3) 0.1342(3) 0.0394(11) Uani 1 1 d . . .
H3W H -0.2172 0.0422 0.1812 0.059 Uiso 1 1 d R . .
H4W H -0.0771 -0.0476 0.1502 0.059 Uiso 1 1 d R . .
O9 O 0.2687(7) 0.2665(3) 0.1802(3) 0.0388(11) Uani 1 1 d . . .
H5W H 0.1594 0.3168 0.1925 0.058 Uiso 1 1 d R . .
H6W H 0.3581 0.2994 0.1314 0.058 Uiso 1 1 d R . .
O10 O 0.6057(7) 0.3686(4) 0.1143(4) 0.0481(12) Uani 1 1 d G . .
H7W H 0.7081 0.3672 0.0661 0.072 Uiso 1 1 d G . .
H8W H 0.5902 0.4258 0.1368 0.072 Uiso 1 1 d G . .
N1 N 0.3686(9) -0.1669(4) 0.5801(4) 0.0456(15) Uani 1 1 d . . .
N2 N -0.0248(8) 0.5472(4) -0.2412(4) 0.0370(13) Uani 1 1 d . . .
N3 N 0.5046(8) 0.4471(4) -0.1959(4) 0.0354(13) Uani 1 1 d . . .
F1 F 0.9084(6) -0.2020(3) 0.4949(3) 0.0680(14) Uani 1 1 d . . .
F2 F 0.2071(7) 0.4054(3) -0.4404(3) 0.0687(13) Uani 1 1 d . . .
F3 F 0.7265(8) 0.3527(3) -0.4252(3) 0.0752(14) Uani 1 1 d . . .
C1 C 0.3506(9) -0.0014(4) 0.3100(4) 0.0263(13) Uani 1 1 d . . .
C2 C 0.4362(9) -0.0712(4) 0.4051(4) 0.0257(13) Uani 1 1 d . . .
C3 C 0.3054(10) -0.1053(5) 0.4936(5) 0.0403(17) Uani 1 1 d . . .
H3 H 0.1657 -0.0845 0.4932 0.048 Uiso 1 1 calc R . .
C4 C 0.5700(11) -0.1980(5) 0.5788(5) 0.0438(18) Uani 1 1 d . . .
H4 H 0.6184 -0.2412 0.6379 0.053 Uiso 1 1 calc R . .
C5 C 0.7053(10) -0.1673(5) 0.4920(5) 0.0400(17) Uani 1 1 d . . .
C6 C 0.6446(9) -0.1016(5) 0.4027(4) 0.0315(15) Uani 1 1 d . . .
H6 H 0.7378 -0.0790 0.3445 0.038 Uiso 1 1 calc R . .
C7 C 0.0567(9) 0.2650(5) -0.0689(5) 0.0275(14) Uani 1 1 d . . .
C8 C 0.0526(8) 0.3554(4) -0.1663(4) 0.0242(13) Uani 1 1 d . . .
C9 C -0.0239(9) 0.4637(4) -0.1590(5) 0.0316(15) Uani 1 1 d . . .
H9 H -0.0764 0.4781 -0.0942 0.038 Uiso 1 1 calc R . .
C10 C 0.0526(10) 0.5259(5) -0.3333(5) 0.0422(17) Uani 1 1 d . . .
H10 H 0.0547 0.5834 -0.3912 0.051 Uiso 1 1 calc R . .
C11 C 0.1293(10) 0.4216(5) -0.3451(4) 0.0372(16) Uani 1 1 d . . .
C12 C 0.1300(9) 0.3341(5) -0.2615(4) 0.0323(15) Uani 1 1 d . . .
H12 H 0.1812 0.2632 -0.2695 0.039 Uiso 1 1 calc R . .
C13 C 0.5963(8) 0.1465(4) -0.0694(4) 0.0228(13) Uani 1 1 d . . .
C14 C 0.5966(8) 0.2512(4) -0.1522(4) 0.0249(13) Uani 1 1 d . . .
C15 C 0.5139(8) 0.3515(4) -0.1274(5) 0.0274(13) Uani 1 1 d . . .
H15 H 0.4617 0.3521 -0.0586 0.033 Uiso 1 1 calc R . .
C16 C 0.5764(10) 0.4442(5) -0.2944(5) 0.0408(18) Uani 1 1 d . . .
H16 H 0.5690 0.5092 -0.3443 0.049 Uiso 1 1 calc R . .
C17 C 0.6597(10) 0.3491(5) -0.3237(5) 0.0410(17) Uani 1 1 d . . .
C18 C 0.6757(9) 0.2502(5) -0.2545(5) 0.0371(16) Uani 1 1 d . . .
H18 H 0.7367 0.1856 -0.2751 0.045 Uiso 1 1 calc 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 O6 2.388(4) 2_655 ?
Pr1 O5 2.416(4) . ?
Pr1 O7 2.482(4) . ?
Pr1 O9 2.497(4) . ?
Pr1 O8 2.507(4) . ?
Pr1 O2 2.527(3) . ?
Pr1 O4 2.579(4) . ?
Pr1 O1 2.585(4) . ?
Pr1 O3 2.731(4) . ?
O1 C1 1.250(6) . ?
O2 C1 1.259(6) . ?
O3 C7 1.237(7) . ?
O4 C7 1.258(7) . ?
O5 C13 1.251(7) . ?
O6 C13 1.236(7) . ?
O6 Pr1 2.388(4) 2_655 ?
O7 H1W 0.8846 . ?
O7 H2W 0.8838 . ?
O8 H3W 0.8774 . ?
O8 H4W 0.8776 . ?
O9 H5W 0.8888 . ?
O9 H6W 0.8880 . ?
O10 H7W 0.8501 . ?
O10 H8W 0.8499 . ?
N1 C3 1.333(7) . ?
N1 C4 1.338(8) . ?
N2 C10 1.328(8) . ?
N2 C9 1.335(7) . ?
N3 C15 1.335(7) . ?
N3 C16 1.336(8) . ?
F1 C5 1.361(7) . ?
F2 C11 1.347(7) . ?
F3 C17 1.353(7) . ?
C1 C2 1.518(7) . ?
C2 C3 1.372(8) . ?
C2 C6 1.382(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.363(9) . ?
C4 H4 0.9300 . ?
C5 C6 1.374(8) . ?
C6 H6 0.9300 . ?
C7 C8 1.521(7) . ?
C8 C12 1.367(8) . ?
C8 C9 1.400(8) . ?
C9 H9 0.9300 . ?
C10 C11 1.370(9) . ?
C10 H10 0.9300 . ?
C11 C12 1.377(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.516(7) . ?
C14 C18 1.386(8) . ?
C14 C15 1.389(8) . ?
C15 H15 0.9300 . ?
C16 C17 1.355(10) . ?
C16 H16 0.9300 . ?
C17 C18 1.372(8) . ?
C18 H18 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O6 Pr1 O5 83.52(13) 2_655 . ?
O6 Pr1 O7 135.99(13) 2_655 . ?
O5 Pr1 O7 140.47(13) . . ?
O6 Pr1 O9 144.21(14) 2_655 . ?
O5 Pr1 O9 73.38(14) . . ?
O7 Pr1 O9 70.82(15) . . ?
O6 Pr1 O8 69.42(14) 2_655 . ?
O5 Pr1 O8 140.70(14) . . ?
O7 Pr1 O8 72.14(15) . . ?
O9 Pr1 O8 142.95(15) . . ?
O6 Pr1 O2 84.00(14) 2_655 . ?
O5 Pr1 O2 122.64(12) . . ?
O7 Pr1 O2 70.92(13) . . ?
O9 Pr1 O2 85.91(14) . . ?
O8 Pr1 O2 83.33(13) . . ?
O6 Pr1 O4 131.08(14) 2_655 . ?
O5 Pr1 O4 86.87(13) . . ?
O7 Pr1 O4 68.44(13) . . ?
O9 Pr1 O4 75.38(14) . . ?
O8 Pr1 O4 90.00(14) . . ?
O2 Pr1 O4 138.90(14) . . ?
O6 Pr1 O1 75.66(14) 2_655 . ?
O5 Pr1 O1 71.64(12) . . ?
O7 Pr1 O1 111.10(13) . . ?
O9 Pr1 O1 71.35(13) . . ?
O8 Pr1 O1 124.69(12) . . ?
O2 Pr1 O1 51.02(12) . . ?
O4 Pr1 O1 144.30(14) . . ?
O6 Pr1 O3 83.20(13) 2_655 . ?
O5 Pr1 O3 70.18(13) . . ?
O7 Pr1 O3 109.38(13) . . ?
O9 Pr1 O3 112.83(12) . . ?
O8 Pr1 O3 78.54(13) . . ?
O2 Pr1 O3 160.59(13) . . ?
O4 Pr1 O3 48.65(13) . . ?
O1 Pr1 O3 137.96(13) . . ?
C1 O1 Pr1 91.8(3) . . ?
C1 O2 Pr1 94.3(3) . . ?
C7 O3 Pr1 89.8(4) . . ?
C7 O4 Pr1 96.4(3) . . ?
C13 O5 Pr1 141.4(4) . . ?
C13 O6 Pr1 166.2(4) . 2_655 ?
Pr1 O7 H1W 111.1 . . ?
Pr1 O7 H2W 110.7 . . ?
H1W O7 H2W 107.8 . . ?
Pr1 O8 H3W 110.5 . . ?
Pr1 O8 H4W 110.5 . . ?
H3W O8 H4W 108.2 . . ?
Pr1 O9 H5W 111.2 . . ?
Pr1 O9 H6W 110.9 . . ?
H5W O9 H6W 107.6 . . ?
H7W O10 H8W 109.5 . . ?
C3 N1 C4 117.6(6) . . ?
C10 N2 C9 118.2(6) . . ?
C15 N3 C16 116.9(6) . . ?
O1 C1 O2 122.7(5) . . ?
O1 C1 C2 119.1(5) . . ?
O2 C1 C2 118.1(5) . . ?
C3 C2 C6 119.9(5) . . ?
C3 C2 C1 119.7(5) . . ?
C6 C2 C1 120.4(5) . . ?
N1 C3 C2 123.3(6) . . ?
N1 C3 H3 118.4 . . ?
C2 C3 H3 118.4 . . ?
N1 C4 C5 121.0(5) . . ?
N1 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
F1 C5 C4 118.5(5) . . ?
F1 C5 C6 118.9(6) . . ?
C4 C5 C6 122.6(6) . . ?
C5 C6 C2 115.6(6) . . ?
C5 C6 H6 122.2 . . ?
C2 C6 H6 122.2 . . ?
O3 C7 O4 122.9(5) . . ?
O3 C7 C8 119.4(6) . . ?
O4 C7 C8 117.6(5) . . ?
C12 C8 C9 118.7(5) . . ?
C12 C8 C7 121.4(5) . . ?
C9 C8 C7 119.8(5) . . ?
N2 C9 C8 122.7(6) . . ?
N2 C9 H9 118.6 . . ?
C8 C9 H9 118.6 . . ?
N2 C10 C11 121.6(5) . . ?
N2 C10 H10 119.2 . . ?
C11 C10 H10 119.2 . . ?
F2 C11 C10 118.8(5) . . ?
F2 C11 C12 120.0(6) . . ?
C10 C11 C12 121.2(6) . . ?
C8 C12 C11 117.5(6) . . ?
C8 C12 H12 121.2 . . ?
C11 C12 H12 121.2 . . ?
O6 C13 O5 127.1(5) . . ?
O6 C13 C14 116.9(5) . . ?
O5 C13 C14 115.9(5) . . ?
C18 C14 C15 118.0(5) . . ?
C18 C14 C13 121.5(6) . . ?
C15 C14 C13 120.5(5) . . ?
N3 C15 C14 124.2(6) . . ?
N3 C15 H15 117.9 . . ?
C14 C15 H15 117.9 . . ?
N3 C16 C17 121.9(5) . . ?
N3 C16 H16 119.1 . . ?
C17 C16 H16 119.1 . . ?
F3 C17 C16 118.4(5) . . ?
F3 C17 C18 119.3(7) . . ?
C16 C17 C18 122.3(6) . . ?
C17 C18 C14 116.7(6) . . ?
C17 C18 H18 121.7 . . ?
C14 C18 H18 121.7 . . ?

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
O6 Pr1 O1 C1 -91.9(4) 2_655 . . . ?
O5 Pr1 O1 C1 -179.8(4) . . . . ?
O7 Pr1 O1 C1 42.3(4) . . . . ?
O9 Pr1 O1 C1 102.1(4) . . . . ?
O8 Pr1 O1 C1 -40.1(4) . . . . ?
O2 Pr1 O1 C1 2.0(3) . . . . ?
O4 Pr1 O1 C1 124.3(4) . . . . ?
O3 Pr1 O1 C1 -154.1(3) . . . . ?
O6 Pr1 O2 C1 74.4(4) 2_655 . . . ?
O5 Pr1 O2 C1 -3.9(4) . . . . ?
O7 Pr1 O2 C1 -142.3(4) . . . . ?
O9 Pr1 O2 C1 -71.2(4) . . . . ?
O8 Pr1 O2 C1 144.3(4) . . . . ?
O4 Pr1 O2 C1 -133.4(4) . . . . ?
O1 Pr1 O2 C1 -2.0(3) . . . . ?
O3 Pr1 O2 C1 123.4(4) . . . . ?
O6 Pr1 O3 C7 178.8(4) 2_655 . . . ?
O5 Pr1 O3 C7 -95.6(3) . . . . ?
O7 Pr1 O3 C7 42.3(4) . . . . ?
O9 Pr1 O3 C7 -34.4(4) . . . . ?
O8 Pr1 O3 C7 108.5(4) . . . . ?
O2 Pr1 O3 C7 129.8(4) . . . . ?
O4 Pr1 O3 C7 8.3(3) . . . . ?
O1 Pr1 O3 C7 -121.5(3) . . . . ?
O6 Pr1 O4 C7 -20.6(4) 2_655 . . . ?
O5 Pr1 O4 C7 58.0(4) . . . . ?
O7 Pr1 O4 C7 -153.6(4) . . . . ?
O9 Pr1 O4 C7 131.6(4) . . . . ?
O8 Pr1 O4 C7 -82.8(4) . . . . ?
O2 Pr1 O4 C7 -162.7(3) . . . . ?
O1 Pr1 O4 C7 109.9(4) . . . . ?
O3 Pr1 O4 C7 -8.2(3) . . . . ?
O6 Pr1 O5 C13 50.7(6) 2_655 . . . ?
O7 Pr1 O5 C13 -131.1(5) . . . . ?
O9 Pr1 O5 C13 -157.0(6) . . . . ?
O8 Pr1 O5 C13 4.9(7) . . . . ?
O2 Pr1 O5 C13 129.3(6) . . . . ?
O4 Pr1 O5 C13 -81.3(6) . . . . ?
O1 Pr1 O5 C13 127.7(6) . . . . ?
O3 Pr1 O5 C13 -34.4(6) . . . . ?
Pr1 O1 C1 O2 -3.7(6) . . . . ?
Pr1 O1 C1 C2 174.9(5) . . . . ?
Pr1 O2 C1 O1 3.8(6) . . . . ?
Pr1 O2 C1 C2 -174.8(4) . . . . ?
O1 C1 C2 C3 175.7(6) . . . . ?
O2 C1 C2 C3 -5.7(9) . . . . ?
O1 C1 C2 C6 -5.0(9) . . . . ?
O2 C1 C2 C6 173.6(6) . . . . ?
C4 N1 C3 C2 -1.3(10) . . . . ?
C6 C2 C3 N1 0.6(10) . . . . ?
C1 C2 C3 N1 179.9(6) . . . . ?
C3 N1 C4 C5 0.2(10) . . . . ?
N1 C4 C5 F1 -179.5(6) . . . . ?
N1 C4 C5 C6 1.5(11) . . . . ?
F1 C5 C6 C2 178.9(6) . . . . ?
C4 C5 C6 C2 -2.1(10) . . . . ?
C3 C2 C6 C5 1.1(9) . . . . ?
C1 C2 C6 C5 -178.2(6) . . . . ?
Pr1 O3 C7 O4 -15.3(6) . . . . ?
Pr1 O3 C7 C8 160.7(5) . . . . ?
Pr1 O4 C7 O3 16.3(6) . . . . ?
Pr1 O4 C7 C8 -159.7(4) . . . . ?
O3 C7 C8 C12 -1.7(9) . . . . ?
O4 C7 C8 C12 174.5(6) . . . . ?
O3 C7 C8 C9 -179.0(5) . . . . ?
O4 C7 C8 C9 -2.8(8) . . . . ?
C10 N2 C9 C8 -0.8(9) . . . . ?
C12 C8 C9 N2 0.1(9) . . . . ?
C7 C8 C9 N2 177.5(5) . . . . ?
C9 N2 C10 C11 0.9(10) . . . . ?
N2 C10 C11 F2 -179.5(6) . . . . ?
N2 C10 C11 C12 -0.2(11) . . . . ?
C9 C8 C12 C11 0.5(9) . . . . ?
C7 C8 C12 C11 -176.8(5) . . . . ?
F2 C11 C12 C8 178.8(6) . . . . ?
C10 C11 C12 C8 -0.5(10) . . . . ?
Pr1 O6 C13 O5 56.2(19) 2_655 . . . ?
Pr1 O6 C13 C14 -124.6(14) 2_655 . . . ?
Pr1 O5 C13 O6 -74.3(8) . . . . ?
Pr1 O5 C13 C14 106.5(6) . . . . ?
O6 C13 C14 C18 11.9(8) . . . . ?
O5 C13 C14 C18 -168.8(5) . . . . ?
O6 C13 C14 C15 -169.1(5) . . . . ?
O5 C13 C14 C15 10.3(8) . . . . ?
C16 N3 C15 C14 1.4(9) . . . . ?
C18 C14 C15 N3 0.4(9) . . . . ?
C13 C14 C15 N3 -178.7(5) . . . . ?
C15 N3 C16 C17 -1.6(9) . . . . ?
N3 C16 C17 F3 179.1(6) . . . . ?
N3 C16 C17 C18 0.0(11) . . . . ?
F3 C17 C18 C14 -177.2(6) . . . . ?
C16 C17 C18 C14 1.8(10) . . . . ?
C15 C14 C18 C17 -2.0(9) . . . . ?
C13 C14 C18 C17 177.1(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O7 H1W N1 0.88 2.03 2.746(7) 136.9 2_556
O7 H2W O10 0.88 2.06 2.821(6) 143.2 1_455
O8 H3W O1 0.88 2.11 2.843(6) 141.0 1_455
O8 H4W O3 0.88 2.21 2.836(6) 128.4 2
O9 H5W N2 0.89 2.00 2.810(7) 151.2 2_565
O9 H6W O10 0.89 2.03 2.771(6) 140.7 .
O10 H7W O4 0.85 2.05 2.805(7) 147.7 1_655
O10 H8W N3 0.85 1.94 2.774(7) 168.0 2_665

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.771
_refine_diff_density_min         -1.156
_refine_diff_density_rms         0.144
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_227-9nd1
_database_code_depnum_ccdc_archive 'CCDC 1434382'
_audit_update_record             
;
2015-10-30 deposited with the CCDC.
2016-02-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H17 F3 N3 Nd O10'
_chemical_formula_weight         636.59

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Nd Nd -0.1943 3.0179 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   6.8060(3)
_cell_length_b                   12.8810(9)
_cell_length_c                   13.6265(8)
_cell_angle_alpha                74.631(6)
_cell_angle_beta                 77.655(5)
_cell_angle_gamma                76.893(5)
_cell_volume                     1106.76(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.910
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             626
_exptl_absorpt_coefficient_mu    2.432
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5816
_exptl_absorpt_correction_T_max  0.7930
_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 APE-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7188
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_sigmaI/netI    0.0732
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.25
_diffrn_reflns_theta_max         25.05
_reflns_number_total             3905
_reflns_number_gt                3427
_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    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0149P)²+1.1212P] 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         3905
_refine_ls_number_parameters     322
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0390
_refine_ls_wR_factor_ref         0.0812
_refine_ls_wR_factor_gt          0.0749
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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
Nd1 Nd 0.17785(4) 0.61561(2) 0.12589(2) 0.02048(10) Uani 1 1 d . . .
O1 O 0.4713(6) 0.5334(3) 0.2307(3) 0.0358(10) Uani 1 1 d . . .
O2 O 0.1616(6) 0.5152(3) 0.3113(3) 0.0367(10) Uani 1 1 d . . .
O3 O 0.1292(6) 0.6688(3) -0.0754(3) 0.0365(10) Uani 1 1 d . . .
O4 O 0.0011(6) 0.7923(3) 0.0165(3) 0.0404(11) Uani 1 1 d . . .
O5 O 0.3005(6) 0.4387(3) 0.0930(3) 0.0336(9) Uani 1 1 d . . .
O6 O 0.5097(5) 0.3447(3) -0.0165(3) 0.0287(9) Uani 1 1 d . . .
O7 O -0.1125(5) 0.5251(3) 0.1329(3) 0.0388(10) Uani 1 1 d . . .
H2W H -0.2118 0.5336 0.1882 0.058 Uiso 1 1 d R . .
H1W H -0.0725 0.4516 0.1381 0.058 Uiso 1 1 d R . .
O8 O -0.1266(6) 0.7043(3) 0.2293(3) 0.0394(10) Uani 1 1 d . . .
H3W H -0.1635 0.6585 0.2866 0.059 Uiso 1 1 d R . .
H4W H -0.2287 0.7261 0.1949 0.059 Uiso 1 1 d R . .
O9 O 0.2691(6) 0.7647(3) 0.1800(3) 0.0390(10) Uani 1 1 d . . .
H5W H 0.1623 0.8205 0.1854 0.058 Uiso 1 1 d R . .
H6W H 0.3713 0.7936 0.1344 0.058 Uiso 1 1 d R . .
O10 O 0.6065(6) 0.8673(3) 0.1147(4) 0.0488(12) Uani 1 1 d . . .
H7W H 0.7141 0.8604 0.0701 0.059 Uiso 1 1 d R . .
H8W H 0.5778 0.9294 0.1302 0.059 Uiso 1 1 d R . .
N1 N 0.3669(8) 0.3332(4) 0.5798(4) 0.0452(14) Uani 1 1 d . . .
N2 N -0.0236(7) 1.0470(4) -0.2404(4) 0.0369(12) Uani 1 1 d . . .
N3 N 0.4957(7) 0.0526(4) 0.1959(4) 0.0382(13) Uani 1 1 d . . .
C1 C 0.3522(9) 0.4979(4) 0.3088(4) 0.0279(13) Uani 1 1 d . . .
C2 C 0.4347(8) 0.4287(4) 0.4030(4) 0.0242(12) Uani 1 1 d . . .
C3 C 0.6436(9) 0.3980(5) 0.4037(5) 0.0355(15) Uani 1 1 d . . .
C4 C 0.7038(9) 0.3334(5) 0.4924(5) 0.0390(16) Uani 1 1 d . . .
C5 C 0.5700(11) 0.3017(6) 0.5784(5) 0.0451(18) Uani 1 1 d . . .
C6 C 0.3051(9) 0.3947(5) 0.4929(4) 0.0369(15) Uani 1 1 d . . .
H6 H 0.1651 0.4161 0.4928 0.044 Uiso 1 1 calc R . .
C7 C 0.0586(8) 0.7652(5) -0.0689(4) 0.0275(13) Uani 1 1 d . . .
C8 C 0.0516(8) 0.8548(4) -0.1641(4) 0.0236(12) Uani 1 1 d . . .
C9 C 0.1305(9) 0.8334(5) -0.2609(4) 0.0339(14) Uani 1 1 d . . .
H9 H 0.1824 0.7624 -0.2691 0.041 Uiso 1 1 calc R . .
C10 C 0.1288(9) 0.9217(5) -0.3442(4) 0.0374(15) Uani 1 1 d . . .
C11 C 0.0527(9) 1.0269(5) -0.3336(5) 0.0386(15) Uani 1 1 d . . .
H11 H 0.0544 1.0846 -0.3915 0.046 Uiso 1 1 calc R . .
C12 C -0.0236(8) 0.9627(4) -0.1590(4) 0.0305(13) Uani 1 1 d . . .
H12 H -0.0778 0.9773 -0.0944 0.037 Uiso 1 1 calc R . .
C13 C 0.4039(7) 0.3529(4) 0.0689(4) 0.0219(12) Uani 1 1 d . . .
C14 C 0.4036(7) 0.2488(4) 0.1520(4) 0.0235(12) Uani 1 1 d . . .
C15 C 0.4861(8) 0.1488(4) 0.1272(5) 0.0300(13) Uani 1 1 d . . .
H15 H 0.5382 0.1483 0.0584 0.036 Uiso 1 1 calc R . .
C16 C 0.4234(9) 0.0546(5) 0.2942(5) 0.0415(16) Uani 1 1 d . . .
H16 H 0.4287 -0.0110 0.3437 0.050 Uiso 1 1 calc R . .
C17 C 0.3404(9) 0.1517(5) 0.3245(4) 0.0404(16) Uani 1 1 d . . .
C18 C 0.3237(8) 0.2500(5) 0.2543(4) 0.0338(14) Uani 1 1 d . . .
H18 H 0.2614 0.3149 0.2743 0.041 Uiso 1 1 calc R . .
F2 F 0.2067(7) 0.9050(3) -0.4398(3) 0.0702(13) Uani 1 1 d . . .
F3 F 0.2706(7) 0.1474(4) 0.4259(3) 0.0782(14) Uani 1 1 d . . .
H3 H 0.739(8) 0.414(4) 0.359(4) 0.023(16) Uiso 1 1 d . . .
H5 H 0.602(8) 0.261(4) 0.640(4) 0.031(16) Uiso 1 1 d . . .
F1 F 0.9063(5) 0.2976(3) 0.4965(3) 0.0500(10) 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
Nd1 O5 2.368(4) . ?
Nd1 O6 2.396(4) 2_665 ?
Nd1 O9 2.471(4) . ?
Nd1 O8 2.473(4) . ?
Nd1 O7 2.486(4) . ?
Nd1 O2 2.506(4) . ?
Nd1 O4 2.565(4) . ?
Nd1 O1 2.571(3) . ?
Nd1 O3 2.719(4) . ?
O1 C1 1.241(7) . ?
O2 C1 1.260(6) . ?
O3 C7 1.245(6) . ?
O4 C7 1.260(7) . ?
O5 C13 1.251(6) . ?
O6 C13 1.247(6) . ?
O6 Nd1 2.396(4) 2_665 ?
O7 H2W 0.9105 . ?
O7 H1W 0.9110 . ?
O8 H3W 0.8729 . ?
O8 H4W 0.8726 . ?
O9 H5W 0.9052 . ?
O9 H6W 0.9038 . ?
O10 H7W 0.8493 . ?
O10 H8W 0.8505 . ?
N1 C6 1.331(7) . ?
N1 C5 1.347(8) . ?
N2 C12 1.331(7) . ?
N2 C11 1.334(7) . ?
N3 C16 1.329(8) . ?
N3 C15 1.338(7) . ?
C1 C2 1.493(7) . ?
C2 C6 1.378(8) . ?
C2 C3 1.389(7) . ?
C3 C4 1.358(8) . ?
C3 H3 0.81(5) . ?
C4 C5 1.352(9) . ?
C4 F1 1.359(6) . ?
C5 H5 0.90(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.491(7) . ?
C8 C12 1.382(7) . ?
C8 C9 1.388(8) . ?
C9 C10 1.378(8) . ?
C9 H9 0.9300 . ?
C10 F2 1.350(7) . ?
C10 C11 1.372(8) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.508(7) . ?
C14 C15 1.383(7) . ?
C14 C18 1.386(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.381(9) . ?
C16 H16 0.9300 . ?
C17 F3 1.352(7) . ?
C17 C18 1.368(8) . ?
C18 H18 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O5 Nd1 O6 83.46(13) . 2_665 ?
O5 Nd1 O9 144.21(13) . . ?
O6 Nd1 O9 73.51(13) 2_665 . ?
O5 Nd1 O8 136.03(14) . . ?
O6 Nd1 O8 140.49(13) 2_665 . ?
O9 Nd1 O8 70.84(14) . . ?
O5 Nd1 O7 69.60(13) . . ?
O6 Nd1 O7 140.36(13) 2_665 . ?
O9 Nd1 O7 142.91(13) . . ?
O8 Nd1 O7 72.10(14) . . ?
O5 Nd1 O2 83.97(13) . . ?
O6 Nd1 O2 122.91(12) 2_665 . ?
O9 Nd1 O2 86.01(14) . . ?
O8 Nd1 O2 70.99(12) . . ?
O7 Nd1 O2 83.60(13) . . ?
O5 Nd1 O4 131.09(13) . . ?
O6 Nd1 O4 86.35(12) 2_665 . ?
O9 Nd1 O4 75.18(13) . . ?
O8 Nd1 O4 68.64(12) . . ?
O7 Nd1 O4 89.99(13) . . ?
O2 Nd1 O4 139.13(13) . . ?
O5 Nd1 O1 75.41(13) . . ?
O6 Nd1 O1 71.82(12) 2_665 . ?
O9 Nd1 O1 71.60(13) . . ?
O8 Nd1 O1 111.36(13) . . ?
O7 Nd1 O1 124.94(13) . . ?
O2 Nd1 O1 51.12(12) . . ?
O4 Nd1 O1 144.18(14) . . ?
O5 Nd1 O3 82.77(12) . . ?
O6 Nd1 O3 69.84(12) 2_665 . ?
O9 Nd1 O3 113.11(12) . . ?
O8 Nd1 O3 109.66(12) . . ?
O7 Nd1 O3 78.14(13) . . ?
O2 Nd1 O3 160.29(13) . . ?
O4 Nd1 O3 49.00(12) . . ?
O1 Nd1 O3 137.55(12) . . ?
C1 O1 Nd1 91.9(3) . . ?
C1 O2 Nd1 94.5(3) . . ?
C7 O3 Nd1 89.8(3) . . ?
C7 O4 Nd1 96.7(3) . . ?
C13 O5 Nd1 166.7(4) . . ?
C13 O6 Nd1 142.4(3) . 2_665 ?
Nd1 O7 H2W 112.0 . . ?
Nd1 O7 H1W 112.2 . . ?
H2W O7 H1W 106.5 . . ?
Nd1 O8 H3W 110.4 . . ?
Nd1 O8 H4W 110.4 . . ?
H3W O8 H4W 108.3 . . ?
Nd1 O9 H5W 112.1 . . ?
Nd1 O9 H6W 111.7 . . ?
H5W O9 H6W 106.8 . . ?
H7W O10 H8W 112.9 . . ?
C6 N1 C5 117.1(6) . . ?
C12 N2 C11 118.3(5) . . ?
C16 N3 C15 117.3(5) . . ?
O1 C1 O2 122.3(5) . . ?
O1 C1 C2 119.8(5) . . ?
O2 C1 C2 117.8(5) . . ?
C6 C2 C3 117.7(5) . . ?
C6 C2 C1 120.9(5) . . ?
C3 C2 C1 121.4(5) . . ?
C4 C3 C2 117.1(6) . . ?
C4 C3 H3 113(4) . . ?
C2 C3 H3 130(4) . . ?
C5 C4 C3 122.8(6) . . ?
C5 C4 F1 117.5(5) . . ?
C3 C4 F1 119.7(6) . . ?
N1 C5 C4 120.8(6) . . ?
N1 C5 H5 113(3) . . ?
C4 C5 H5 126(3) . . ?
N1 C6 C2 124.4(5) . . ?
N1 C6 H6 117.8 . . ?
C2 C6 H6 117.8 . . ?
O3 C7 O4 122.4(5) . . ?
O3 C7 C8 120.2(5) . . ?
O4 C7 C8 117.3(5) . . ?
C12 C8 C9 117.5(5) . . ?
C12 C8 C7 121.4(5) . . ?
C9 C8 C7 121.0(5) . . ?
C10 C9 C8 117.3(5) . . ?
C10 C9 H9 121.4 . . ?
C8 C9 H9 121.4 . . ?
F2 C10 C11 118.4(5) . . ?
F2 C10 C9 119.4(6) . . ?
C11 C10 C9 122.2(6) . . ?
N2 C11 C10 120.3(5) . . ?
N2 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
N2 C12 C8 124.4(5) . . ?
N2 C12 H12 117.8 . . ?
C8 C12 H12 117.8 . . ?
O6 C13 O5 126.7(5) . . ?
O6 C13 C14 116.5(5) . . ?
O5 C13 C14 116.8(5) . . ?
C15 C14 C18 118.2(5) . . ?
C15 C14 C13 120.1(5) . . ?
C18 C14 C13 121.8(5) . . ?
N3 C15 C14 124.2(6) . . ?
N3 C15 H15 117.9 . . ?
C14 C15 H15 117.9 . . ?
N3 C16 C17 121.6(5) . . ?
N3 C16 H16 119.2 . . ?
C17 C16 H16 119.2 . . ?
F3 C17 C18 120.2(6) . . ?
F3 C17 C16 118.3(5) . . ?
C18 C17 C16 121.4(6) . . ?
C17 C18 C14 117.3(6) . . ?
C17 C18 H18 121.4 . . ?
C14 C18 H18 121.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O5 Nd1 O1 C1 -92.6(3) . . . . ?
O6 Nd1 O1 C1 179.6(4) 2_665 . . . ?
O9 Nd1 O1 C1 101.5(4) . . . . ?
O8 Nd1 O1 C1 41.6(4) . . . . ?
O7 Nd1 O1 C1 -41.0(4) . . . . ?
O2 Nd1 O1 C1 1.5(3) . . . . ?
O4 Nd1 O1 C1 124.4(3) . . . . ?
O3 Nd1 O1 C1 -154.1(3) . . . . ?
O5 Nd1 O2 C1 74.6(3) . . . . ?
O6 Nd1 O2 C1 -3.6(4) 2_665 . . . ?
O9 Nd1 O2 C1 -71.0(3) . . . . ?
O8 Nd1 O2 C1 -142.1(4) . . . . ?
O7 Nd1 O2 C1 144.7(3) . . . . ?
O4 Nd1 O2 C1 -132.8(3) . . . . ?
O1 Nd1 O2 C1 -1.5(3) . . . . ?
O3 Nd1 O2 C1 122.6(4) . . . . ?
O5 Nd1 O3 C7 179.1(3) . . . . ?
O6 Nd1 O3 C7 -95.3(3) 2_665 . . . ?
O9 Nd1 O3 C7 -34.3(3) . . . . ?
O8 Nd1 O3 C7 42.6(3) . . . . ?
O7 Nd1 O3 C7 108.5(3) . . . . ?
O2 Nd1 O3 C7 131.0(4) . . . . ?
O4 Nd1 O3 C7 8.0(3) . . . . ?
O1 Nd1 O3 C7 -121.9(3) . . . . ?
O5 Nd1 O4 C7 -19.7(4) . . . . ?
O6 Nd1 O4 C7 58.4(3) 2_665 . . . ?
O9 Nd1 O4 C7 132.3(4) . . . . ?
O8 Nd1 O4 C7 -152.9(4) . . . . ?
O7 Nd1 O4 C7 -82.1(3) . . . . ?
O2 Nd1 O4 C7 -162.3(3) . . . . ?
O1 Nd1 O4 C7 109.9(4) . . . . ?
O3 Nd1 O4 C7 -7.9(3) . . . . ?
O6 Nd1 O5 C13 16.7(15) 2_665 . . . ?
O9 Nd1 O5 C13 -33.0(16) . . . . ?
O8 Nd1 O5 C13 -162.0(14) . . . . ?
O7 Nd1 O5 C13 167.1(15) . . . . ?
O2 Nd1 O5 C13 -107.5(15) . . . . ?
O4 Nd1 O5 C13 96.0(15) . . . . ?
O1 Nd1 O5 C13 -56.2(15) . . . . ?
O3 Nd1 O5 C13 87.1(15) . . . . ?
Nd1 O1 C1 O2 -2.7(6) . . . . ?
Nd1 O1 C1 C2 175.0(4) . . . . ?
Nd1 O2 C1 O1 2.8(6) . . . . ?
Nd1 O2 C1 C2 -174.9(4) . . . . ?
O1 C1 C2 C6 175.5(6) . . . . ?
O2 C1 C2 C6 -6.8(8) . . . . ?
O1 C1 C2 C3 -3.3(9) . . . . ?
O2 C1 C2 C3 174.4(5) . . . . ?
C6 C2 C3 C4 2.3(9) . . . . ?
C1 C2 C3 C4 -178.9(5) . . . . ?
C2 C3 C4 C5 -1.9(10) . . . . ?
C2 C3 C4 F1 177.7(5) . . . . ?
C6 N1 C5 C4 1.2(10) . . . . ?
C3 C4 C5 N1 0.1(11) . . . . ?
F1 C4 C5 N1 -179.4(6) . . . . ?
C5 N1 C6 C2 -0.8(10) . . . . ?
C3 C2 C6 N1 -1.0(10) . . . . ?
C1 C2 C6 N1 -179.8(5) . . . . ?
Nd1 O3 C7 O4 -14.6(5) . . . . ?
Nd1 O3 C7 C8 161.5(4) . . . . ?
Nd1 O4 C7 O3 15.6(6) . . . . ?
Nd1 O4 C7 C8 -160.6(4) . . . . ?
O3 C7 C8 C12 -179.2(5) . . . . ?
O4 C7 C8 C12 -2.9(7) . . . . ?
O3 C7 C8 C9 -2.6(8) . . . . ?
O4 C7 C8 C9 173.7(5) . . . . ?
C12 C8 C9 C10 0.4(8) . . . . ?
C7 C8 C9 C10 -176.3(5) . . . . ?
C8 C9 C10 F2 179.0(5) . . . . ?
C8 C9 C10 C11 -0.1(9) . . . . ?
C12 N2 C11 C10 0.1(8) . . . . ?
F2 C10 C11 N2 -179.3(5) . . . . ?
C9 C10 C11 N2 -0.2(9) . . . . ?
C11 N2 C12 C8 0.3(8) . . . . ?
C9 C8 C12 N2 -0.6(8) . . . . ?
C7 C8 C12 N2 176.1(5) . . . . ?
Nd1 O6 C13 O5 72.8(7) 2_665 . . . ?
Nd1 O6 C13 C14 -106.2(6) 2_665 . . . ?
Nd1 O5 C13 O6 -55.7(17) . . . . ?
Nd1 O5 C13 C14 123.4(14) . . . . ?
O6 C13 C14 C15 -11.3(7) . . . . ?
O5 C13 C14 C15 169.5(5) . . . . ?
O6 C13 C14 C18 168.0(5) . . . . ?
O5 C13 C14 C18 -11.1(7) . . . . ?
C16 N3 C15 C14 -0.9(8) . . . . ?
C18 C14 C15 N3 -0.7(8) . . . . ?
C13 C14 C15 N3 178.7(5) . . . . ?
C15 N3 C16 C17 0.3(9) . . . . ?
N3 C16 C17 F3 -179.7(5) . . . . ?
N3 C16 C17 C18 1.9(10) . . . . ?
F3 C17 C18 C14 178.2(5) . . . . ?
C16 C17 C18 C14 -3.4(9) . . . . ?
C15 C14 C18 C17 2.7(8) . . . . ?
C13 C14 C18 C17 -176.6(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O10 H8W N3 0.85 1.94 2.779(7) 167.5 1_565
O10 H7W O4 0.85 2.02 2.812(6) 155.3 1_655
O9 H6W O10 0.90 1.98 2.773(6) 146.0 .
O9 H5W N2 0.91 2.00 2.825(6) 150.5 2_575
O8 H4W O10 0.87 2.08 2.809(5) 141.2 1_455
O8 H3W N1 0.87 2.05 2.747(6) 136.4 2_566
O7 H1W O3 0.91 2.10 2.841(6) 137.9 2_565
O7 H2W O1 0.91 2.11 2.852(5) 137.9 1_455

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.041
_refine_diff_density_min         -1.564
_refine_diff_density_rms         0.132
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_229-11eu
_database_code_depnum_ccdc_archive 'CCDC 1434383'
_audit_update_record             
;
2015-10-30 deposited with the CCDC.
2016-02-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H17 Eu F3 N3 O10'
_chemical_formula_weight         644.31

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'
Eu Eu -0.1578 3.6682 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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                   6.7955(4)
_cell_length_b                   12.8007(8)
_cell_length_c                   13.6033(9)
_cell_angle_alpha                74.644(5)
_cell_angle_beta                 77.629(5)
_cell_angle_gamma                76.699(5)
_cell_volume                     1095.54(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.953
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632
_exptl_absorpt_coefficient_mu    2.949
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4923
_exptl_absorpt_correction_T_max  0.5379
_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 APE-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6796
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_sigmaI/netI    0.0595
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.36
_diffrn_reflns_theta_max         25.05
_reflns_number_total             3861
_reflns_number_gt                3445
_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    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0194P)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         3861
_refine_ls_number_parameters     322
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0311
_refine_ls_wR_factor_ref         0.0630
_refine_ls_wR_factor_gt          0.0584
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Eu1 Eu 0.31949(3) 0.384851(18) 0.374110(17) 0.01983(8) Uani 1 1 d . . .
O1 O 0.3692(5) 0.3341(3) 0.5756(3) 0.0386(9) Uani 1 1 d . . .
O2 O 0.4932(5) 0.2108(3) 0.4814(3) 0.0383(9) Uani 1 1 d . . .
O3 O 0.0244(4) 0.4663(3) 0.2712(3) 0.0342(8) Uani 1 1 d . . .
O4 O 0.3375(4) 0.4854(3) 0.1924(3) 0.0348(8) Uani 1 1 d . . .
O5 O 0.1977(4) 0.5591(2) 0.4082(3) 0.0307(8) Uani 1 1 d . . .
O6 O -0.0132(4) 0.6543(3) 0.5167(3) 0.0301(8) Uani 1 1 d . . .
O7 O 0.6072(4) 0.4730(3) 0.3666(3) 0.0379(9) Uani 1 1 d . . .
H1W H 0.7120 0.4237 0.3813 0.057 Uiso 1 1 d R . .
H2W H 0.5747 0.5137 0.4105 0.057 Uiso 1 1 d R . .
O8 O 0.6230(4) 0.2974(3) 0.2720(3) 0.0384(8) Uani 1 1 d . . .
H4W H 0.6345 0.3348 0.2099 0.058 Uiso 1 1 d R . .
H3W H 0.6100 0.2324 0.2735 0.058 Uiso 1 1 d R . .
O9 O 0.2276(5) 0.2366(3) 0.3223(3) 0.0387(9) Uani 1 1 d . . .
H5W H 0.3333 0.1831 0.3172 0.058 Uiso 1 1 d R . .
H6W H 0.1871 0.2807 0.2621 0.058 Uiso 1 1 d R . .
O10 O 0.8906(5) 0.1348(3) 0.3856(4) 0.0478(10) Uani 1 1 d G . .
H8W H 0.7790 0.1382 0.4281 0.072 Uiso 1 1 d G . .
H7W H 0.9228 0.0720 0.3707 0.072 Uiso 1 1 d G . .
N1 N 0.5248(6) -0.0480(3) 0.7384(4) 0.0375(10) Uani 1 1 d . . .
N2 N 0.1389(6) 0.6668(4) -0.0790(3) 0.0435(11) Uani 1 1 d . . .
N3 N 0.0052(6) 0.9480(3) 0.3047(4) 0.0358(10) Uani 1 1 d . . .
C1 C 0.4397(6) 0.2373(4) 0.5678(4) 0.0279(11) Uani 1 1 d . . .
C2 C 0.4456(6) 0.1458(4) 0.6641(4) 0.0237(10) Uani 1 1 d . . .
C3 C 0.5230(7) 0.0368(4) 0.6574(4) 0.0302(11) Uani 1 1 d . . .
H3 H 0.5765 0.0227 0.5923 0.036 Uiso 1 1 calc R . .
C4 C 0.4464(7) -0.0273(4) 0.8312(4) 0.0401(13) Uani 1 1 d . . .
H4 H 0.4438 -0.0855 0.8891 0.048 Uiso 1 1 calc R . .
C5 C 0.3695(7) 0.0782(4) 0.8430(4) 0.0361(12) Uani 1 1 d . . .
C6 C 0.3682(7) 0.1664(4) 0.7606(4) 0.0339(12) Uani 1 1 d . . .
H6 H 0.3167 0.2378 0.7693 0.041 Uiso 1 1 calc R . .
C7 C 0.1459(7) 0.5015(4) 0.1933(4) 0.0267(11) Uani 1 1 d . . .
C8 C 0.0655(6) 0.5710(4) 0.0967(4) 0.0247(10) Uani 1 1 d . . .
C9 C 0.1979(7) 0.6059(4) 0.0085(4) 0.0366(13) Uani 1 1 d . . .
H9 H 0.3378 0.5855 0.0104 0.044 Uiso 1 1 calc R . .
C10 C -0.0618(8) 0.6983(4) -0.0797(4) 0.0430(14) Uani 1 1 d . . .
H10 H -0.1080 0.7424 -0.1396 0.052 Uiso 1 1 calc R . .
C11 C -0.2011(7) 0.6671(4) 0.0056(4) 0.0356(13) Uani 1 1 d . . .
C12 C -0.1443(7) 0.6022(4) 0.0961(4) 0.0329(12) Uani 1 1 d . . .
H12 H -0.2401 0.5802 0.1536 0.039 Uiso 1 1 calc R . .
C13 C 0.0934(6) 0.6453(4) 0.4310(4) 0.0228(10) Uani 1 1 d . . .
C14 C 0.0964(6) 0.7506(4) 0.3480(4) 0.0229(10) Uani 1 1 d . . .
C15 C 0.0142(6) 0.8512(4) 0.3735(4) 0.0275(11) Uani 1 1 d . . .
H15 H -0.0380 0.8515 0.4425 0.033 Uiso 1 1 calc R . .
C16 C 0.0770(7) 0.9469(4) 0.2062(5) 0.0414(14) Uani 1 1 d . . .
H16 H 0.0692 1.0130 0.1568 0.050 Uiso 1 1 calc R . .
C17 C 0.1627(8) 0.8495(5) 0.1756(4) 0.0400(13) Uani 1 1 d . . .
C18 C 0.1779(7) 0.7490(4) 0.2469(4) 0.0335(12) Uani 1 1 d . . .
H18 H 0.2404 0.6835 0.2269 0.040 Uiso 1 1 calc R . .
F1 F 0.2905(6) 0.0942(3) 0.9393(3) 0.0729(11) Uani 1 1 d . . .
F2 F -0.4041(4) 0.7022(3) -0.0003(3) 0.0655(10) Uani 1 1 d . . .
F3 F 0.2331(6) 0.8524(3) 0.0750(3) 0.0767(11) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Eu1 O5 2.325(3) . ?
Eu1 O6 2.356(3) 2_566 ?
Eu1 O9 2.436(3) . ?
Eu1 O8 2.443(3) . ?
Eu1 O7 2.444(3) . ?
Eu1 O4 2.458(3) . ?
Eu1 O2 2.509(3) . ?
Eu1 O3 2.557(3) . ?
Eu1 O1 2.720(4) . ?
Eu1 H6W 2.6687 . ?
O1 C1 1.246(5) . ?
O2 C1 1.266(6) . ?
O3 C7 1.245(5) . ?
O4 C7 1.268(5) . ?
O5 C13 1.243(5) . ?
O6 C13 1.252(5) . ?
O6 Eu1 2.356(3) 2_566 ?
O7 H1W 0.8559 . ?
O7 H2W 0.8558 . ?
O8 H4W 0.8508 . ?
O8 H3W 0.8510 . ?
O9 H5W 0.8756 . ?
O9 H6W 0.9195 . ?
O10 H8W 0.8500 . ?
O10 H7W 0.8499 . ?
N1 C3 1.327(6) . ?
N1 C4 1.331(6) . ?
N2 C9 1.325(6) . ?
N2 C10 1.332(6) . ?
N3 C16 1.328(7) . ?
N3 C15 1.338(6) . ?
C1 C2 1.509(6) . ?
C2 C6 1.376(6) . ?
C2 C3 1.393(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.369(7) . ?
C4 H4 0.9300 . ?
C5 F1 1.356(6) . ?
C5 C6 1.364(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.511(6) . ?
C8 C9 1.373(6) . ?
C8 C12 1.391(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.364(7) . ?
C10 H10 0.9300 . ?
C11 F2 1.362(5) . ?
C11 C12 1.366(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.513(6) . ?
C14 C18 1.372(6) . ?
C14 C15 1.383(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.379(7) . ?
C16 H16 0.9300 . ?
C17 F3 1.343(6) . ?
C17 C18 1.388(7) . ?
C18 H18 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O5 Eu1 O6 83.02(11) . 2_566 ?
O5 Eu1 O9 144.11(10) . . ?
O6 Eu1 O9 73.31(11) 2_566 . ?
O5 Eu1 O8 135.93(11) . . ?
O6 Eu1 O8 141.05(11) 2_566 . ?
O9 Eu1 O8 71.81(11) . . ?
O5 Eu1 O7 70.17(10) . . ?
O6 Eu1 O7 140.26(11) 2_566 . ?
O9 Eu1 O7 142.86(11) . . ?
O8 Eu1 O7 71.11(11) . . ?
O5 Eu1 O4 84.07(11) . . ?
O6 Eu1 O4 123.86(10) 2_566 . ?
O9 Eu1 O4 87.13(11) . . ?
O8 Eu1 O4 71.01(11) . . ?
O7 Eu1 O4 82.89(11) . . ?
O5 Eu1 O2 130.58(11) . . ?
O6 Eu1 O2 85.99(11) 2_566 . ?
O9 Eu1 O2 75.03(11) . . ?
O8 Eu1 O2 68.74(11) . . ?
O7 Eu1 O2 89.71(11) . . ?
O4 Eu1 O2 139.31(11) . . ?
O5 Eu1 O3 75.78(10) . . ?
O6 Eu1 O3 71.75(11) 2_566 . ?
O9 Eu1 O3 71.42(11) . . ?
O8 Eu1 O3 111.99(11) . . ?
O7 Eu1 O3 125.65(11) . . ?
O4 Eu1 O3 52.11(10) . . ?
O2 Eu1 O3 143.78(11) . . ?
O5 Eu1 O1 81.59(11) . . ?
O6 Eu1 O1 69.63(10) 2_566 . ?
O9 Eu1 O1 113.47(11) . . ?
O8 Eu1 O1 109.70(10) . . ?
O7 Eu1 O1 77.67(11) . . ?
O4 Eu1 O1 158.85(10) . . ?
O2 Eu1 O1 49.58(10) . . ?
O3 Eu1 O1 137.07(10) . . ?
O5 Eu1 H6W 130.4 . . ?
O6 Eu1 H6W 80.0 2_566 . ?
O9 Eu1 H6W 20.1 . . ?
O8 Eu1 H6W 73.2 . . ?
O7 Eu1 H6W 139.7 . . ?
O4 Eu1 H6W 68.3 . . ?
O2 Eu1 H6W 94.3 . . ?
O3 Eu1 H6W 54.7 . . ?
O1 Eu1 H6W 132.7 . . ?
C1 O1 Eu1 88.4(3) . . ?
C1 O2 Eu1 97.8(3) . . ?
C7 O3 Eu1 90.6(3) . . ?
C7 O4 Eu1 94.7(3) . . ?
C13 O5 Eu1 166.6(3) . . ?
C13 O6 Eu1 142.8(3) . 2_566 ?
Eu1 O7 H1W 109.7 . . ?
Eu1 O7 H2W 109.3 . . ?
H1W O7 H2W 109.1 . . ?
Eu1 O8 H4W 109.2 . . ?
Eu1 O8 H3W 109.2 . . ?
H4W O8 H3W 109.4 . . ?
Eu1 O9 H5W 110.5 . . ?
Eu1 O9 H6W 94.4 . . ?
H5W O9 H6W 117.8 . . ?
H8W O10 H7W 109.5 . . ?
C3 N1 C4 117.7(4) . . ?
C9 N2 C10 117.3(5) . . ?
C16 N3 C15 117.8(5) . . ?
O1 C1 O2 122.4(5) . . ?
O1 C1 C2 119.6(5) . . ?
O2 C1 C2 117.8(4) . . ?
C6 C2 C3 117.9(5) . . ?
C6 C2 C1 121.4(4) . . ?
C3 C2 C1 120.7(4) . . ?
N1 C3 C2 123.8(5) . . ?
N1 C3 H3 118.1 . . ?
C2 C3 H3 118.1 . . ?
N1 C4 C5 121.2(5) . . ?
N1 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
F1 C5 C6 119.6(5) . . ?
F1 C5 C4 118.6(5) . . ?
C6 C5 C4 121.8(5) . . ?
C5 C6 C2 117.6(5) . . ?
C5 C6 H6 121.2 . . ?
C2 C6 H6 121.2 . . ?
O3 C7 O4 122.6(4) . . ?
O3 C7 C8 120.0(4) . . ?
O4 C7 C8 117.4(4) . . ?
C9 C8 C12 118.8(5) . . ?
C9 C8 C7 120.7(4) . . ?
C12 C8 C7 120.4(4) . . ?
N2 C9 C8 124.1(4) . . ?
N2 C9 H9 117.9 . . ?
C8 C9 H9 117.9 . . ?
N2 C10 C11 121.3(5) . . ?
N2 C10 H10 119.3 . . ?
C11 C10 H10 119.3 . . ?
F2 C11 C10 118.3(5) . . ?
F2 C11 C12 119.2(5) . . ?
C10 C11 C12 122.5(4) . . ?
C11 C12 C8 115.9(5) . . ?
C11 C12 H12 122.1 . . ?
C8 C12 H12 122.1 . . ?
O5 C13 O6 126.5(5) . . ?
O5 C13 C14 117.2(4) . . ?
O6 C13 C14 116.2(4) . . ?
C18 C14 C15 118.7(5) . . ?
C18 C14 C13 121.5(4) . . ?
C15 C14 C13 119.8(4) . . ?
N3 C15 C14 123.8(5) . . ?
N3 C15 H15 118.1 . . ?
C14 C15 H15 118.1 . . ?
N3 C16 C17 121.3(5) . . ?
N3 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
F3 C17 C16 119.2(5) . . ?
F3 C17 C18 119.6(5) . . ?
C16 C17 C18 121.2(5) . . ?
C14 C18 C17 117.1(5) . . ?
C14 C18 H18 121.5 . . ?
C17 C18 H18 121.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O5 Eu1 O1 C1 -179.4(3) . . . . ?
O6 Eu1 O1 C1 95.0(3) 2_566 . . . ?
O9 Eu1 O1 C1 34.6(3) . . . . ?
O8 Eu1 O1 C1 -43.5(3) . . . . ?
O7 Eu1 O1 C1 -108.0(3) . . . . ?
O4 Eu1 O1 C1 -131.6(3) . . . . ?
O2 Eu1 O1 C1 -7.6(2) . . . . ?
O3 Eu1 O1 C1 122.2(3) . . . . ?
O5 Eu1 O2 C1 18.4(3) . . . . ?
O6 Eu1 O2 C1 -58.9(3) 2_566 . . . ?
O9 Eu1 O2 C1 -132.7(3) . . . . ?
O8 Eu1 O2 C1 151.3(3) . . . . ?
O7 Eu1 O2 C1 81.6(3) . . . . ?
O4 Eu1 O2 C1 160.3(2) . . . . ?
O3 Eu1 O2 C1 -110.1(3) . . . . ?
O1 Eu1 O2 C1 7.6(2) . . . . ?
O5 Eu1 O3 C7 92.9(3) . . . . ?
O6 Eu1 O3 C7 -179.9(3) 2_566 . . . ?
O9 Eu1 O3 C7 -101.9(3) . . . . ?
O8 Eu1 O3 C7 -41.3(3) . . . . ?
O7 Eu1 O3 C7 40.6(3) . . . . ?
O4 Eu1 O3 C7 -0.7(2) . . . . ?
O2 Eu1 O3 C7 -125.0(3) . . . . ?
O1 Eu1 O3 C7 153.3(2) . . . . ?
O5 Eu1 O4 C7 -75.9(3) . . . . ?
O6 Eu1 O4 C7 1.6(3) 2_566 . . . ?
O9 Eu1 O4 C7 69.3(3) . . . . ?
O8 Eu1 O4 C7 141.0(3) . . . . ?
O7 Eu1 O4 C7 -146.6(3) . . . . ?
O2 Eu1 O4 C7 132.2(3) . . . . ?
O3 Eu1 O4 C7 0.7(2) . . . . ?
O1 Eu1 O4 C7 -123.3(3) . . . . ?
O6 Eu1 O5 C13 -22.6(14) 2_566 . . . ?
O9 Eu1 O5 C13 25.9(15) . . . . ?
O8 Eu1 O5 C13 157.4(13) . . . . ?
O7 Eu1 O5 C13 -172.8(14) . . . . ?
O4 Eu1 O5 C13 102.7(14) . . . . ?
O2 Eu1 O5 C13 -101.2(14) . . . . ?
O3 Eu1 O5 C13 50.3(14) . . . . ?
O1 Eu1 O5 C13 -92.9(14) . . . . ?
Eu1 O1 C1 O2 13.7(4) . . . . ?
Eu1 O1 C1 C2 -160.8(3) . . . . ?
Eu1 O2 C1 O1 -15.1(4) . . . . ?
Eu1 O2 C1 C2 159.5(3) . . . . ?
O1 C1 C2 C6 2.3(6) . . . . ?
O2 C1 C2 C6 -172.5(4) . . . . ?
O1 C1 C2 C3 179.7(4) . . . . ?
O2 C1 C2 C3 5.0(6) . . . . ?
C4 N1 C3 C2 0.5(7) . . . . ?
C6 C2 C3 N1 0.5(6) . . . . ?
C1 C2 C3 N1 -177.0(4) . . . . ?
C3 N1 C4 C5 -1.0(7) . . . . ?
N1 C4 C5 F1 179.6(4) . . . . ?
N1 C4 C5 C6 0.5(8) . . . . ?
F1 C5 C6 C2 -178.5(4) . . . . ?
C4 C5 C6 C2 0.5(7) . . . . ?
C3 C2 C6 C5 -1.0(6) . . . . ?
C1 C2 C6 C5 176.5(4) . . . . ?
Eu1 O3 C7 O4 1.3(4) . . . . ?
Eu1 O3 C7 C8 -175.7(4) . . . . ?
Eu1 O4 C7 O3 -1.3(5) . . . . ?
Eu1 O4 C7 C8 175.7(3) . . . . ?
O3 C7 C8 C9 -176.7(4) . . . . ?
O4 C7 C8 C9 6.1(6) . . . . ?
O3 C7 C8 C12 4.2(7) . . . . ?
O4 C7 C8 C12 -172.9(4) . . . . ?
C10 N2 C9 C8 2.0(8) . . . . ?
C12 C8 C9 N2 -1.1(8) . . . . ?
C7 C8 C9 N2 179.9(5) . . . . ?
C9 N2 C10 C11 -1.4(8) . . . . ?
N2 C10 C11 F2 180.0(4) . . . . ?
N2 C10 C11 C12 -0.1(8) . . . . ?
F2 C11 C12 C8 -179.0(4) . . . . ?
C10 C11 C12 C8 1.1(7) . . . . ?
C9 C8 C12 C11 -0.5(7) . . . . ?
C7 C8 C12 C11 178.6(4) . . . . ?
Eu1 O5 C13 O6 61.5(16) . . . . ?
Eu1 O5 C13 C14 -119.3(13) . . . . ?
Eu1 O6 C13 O5 -72.8(7) 2_566 . . . ?
Eu1 O6 C13 C14 108.1(5) 2_566 . . . ?
O5 C13 C14 C18 12.1(6) . . . . ?
O6 C13 C14 C18 -168.7(4) . . . . ?
O5 C13 C14 C15 -168.5(4) . . . . ?
O6 C13 C14 C15 10.7(6) . . . . ?
C16 N3 C15 C14 1.0(6) . . . . ?
C18 C14 C15 N3 1.4(6) . . . . ?
C13 C14 C15 N3 -178.1(4) . . . . ?
C15 N3 C16 C17 -1.6(7) . . . . ?
N3 C16 C17 F3 179.9(4) . . . . ?
N3 C16 C17 C18 -0.2(7) . . . . ?
C15 C14 C18 C17 -3.0(6) . . . . ?
C13 C14 C18 C17 176.4(4) . . . . ?
F3 C17 C18 C14 -177.6(4) . . . . ?
C16 C17 C18 C14 2.6(7) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O8 H4W N2 0.85 2.09 2.758(5) 134.9 2_665
O7 H2W O1 0.86 2.13 2.830(4) 138.4 2_666
O7 H1W O3 0.86 2.41 2.846(4) 112.6 1_655

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.506
_refine_diff_density_min         -0.637
_refine_diff_density_rms         0.117
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_227-10gd
_database_code_depnum_ccdc_archive 'CCDC 1434384'
_audit_update_record             
;
2015-10-30 deposited with the CCDC.
2016-02-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H17 F3 Gd N3 O10'
_chemical_formula_weight         649.60

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Gd Gd -0.1653 3.9035 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   6.7892(5)
_cell_length_b                   12.7644(12)
_cell_length_c                   13.5843(16)
_cell_angle_alpha                74.594(9)
_cell_angle_beta                 77.659(9)
_cell_angle_gamma                76.719(8)
_cell_volume                     1089.84(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.983
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             636
_exptl_absorpt_coefficient_mu    3.130
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5083
_exptl_absorpt_correction_T_max  0.7051
_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 APE-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7040
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_sigmaI/netI    0.0603
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.27
_diffrn_reflns_theta_max         25.10
_reflns_number_total             3865
_reflns_number_gt                3507
_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    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0315P)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         3865
_refine_ls_number_parameters     327
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0329
_refine_ls_wR_factor_ref         0.0759
_refine_ls_wR_factor_gt          0.0723
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.062
_refine_ls_shift/su_mean         0.002

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Gd1 Gd 0.18123(3) 0.115041(15) 0.625914(16) 0.01928(9) Uani 1 1 d . . .
O1 O 0.1628(6) 0.0148(3) 0.8072(3) 0.0342(9) Uani 1 1 d . . .
O2 O 0.4766(5) 0.0337(3) 0.7286(3) 0.0342(9) Uani 1 1 d . . .
O3 O 0.0098(6) 0.2884(3) 0.5186(3) 0.0370(9) Uani 1 1 d . . .
O4 O 0.1308(6) 0.1646(3) 0.4249(3) 0.0395(10) Uani 1 1 d . . .
O5 O 0.4853(5) 0.1541(2) 0.5169(3) 0.0286(8) Uani 1 1 d . . .
O6 O 0.6973(5) 0.0586(2) 0.4080(3) 0.0306(8) Uani 1 1 d . . .
O7 O 0.2733(6) 0.2624(3) 0.6778(3) 0.0386(9) Uani 1 1 d . . .
H2W H 0.3323 0.2160 0.7311 0.058 Uiso 1 1 d R . .
H1W H 0.1644 0.3087 0.6928 0.058 Uiso 1 1 d R . .
O8 O -0.1209(6) 0.2015(3) 0.7289(3) 0.0391(10) Uani 1 1 d . . .
H3W H -0.1463 0.2718 0.7031 0.059 Uiso 1 1 d R . .
H4W H -0.1000 0.1905 0.7916 0.059 Uiso 1 1 d R . .
O9 O -0.1060(5) 0.0284(3) 0.6326(3) 0.0394(9) Uani 1 1 d . . .
H6W H -0.0868 0.0016 0.5793 0.059 Uiso 1 1 d R . .
H5W H -0.2160 0.0768 0.6331 0.059 Uiso 1 1 d R . .
O10 O 0.6083(8) 0.3648(4) 0.6145(4) 0.0473(12) Uani 1 1 d . . .
N1 N 0.3584(8) -0.1668(4) 1.0783(3) 0.0461(13) Uani 1 1 d . . .
N2 N -0.0240(7) 0.5474(3) 0.2622(4) 0.0360(11) Uani 1 1 d . . .
N3 N 0.5051(7) 0.4483(3) 0.3042(4) 0.0359(11) Uani 1 1 d . . .
C1 C 0.3544(8) -0.0021(4) 0.8058(4) 0.0272(12) Uani 1 1 d . . .
C2 C 0.4350(8) -0.0703(4) 0.9020(4) 0.0270(11) Uani 1 1 d . . .
C3 C 0.2997(9) -0.1059(4) 0.9913(4) 0.0350(13) Uani 1 1 d . . .
H3 H 0.1598 -0.0855 0.9892 0.042 Uiso 1 1 calc R . .
C4 C 0.5602(10) -0.1979(4) 1.0801(4) 0.0439(15) Uani 1 1 d . . .
H4 H 0.6052 -0.2411 1.1408 0.053 Uiso 1 1 calc R . .
C5 C 0.7006(9) -0.1677(4) 0.9954(4) 0.0388(14) Uani 1 1 d . . .
C6 C 0.6430(8) -0.1019(4) 0.9043(4) 0.0325(12) Uani 1 1 d . . .
H6 H 0.7394 -0.0797 0.8470 0.039 Uiso 1 1 calc R . .
C7 C 0.0628(8) 0.2624(4) 0.4318(4) 0.0272(11) Uani 1 1 d . . .
C8 C 0.0541(7) 0.3536(4) 0.3363(4) 0.0246(11) Uani 1 1 d . . .
C9 C -0.0224(8) 0.4627(4) 0.3434(4) 0.0311(12) Uani 1 1 d . . .
H9 H -0.0750 0.4769 0.4086 0.037 Uiso 1 1 calc R . .
C10 C 0.0531(9) 0.5272(4) 0.1701(4) 0.0419(14) Uani 1 1 d . . .
H10 H 0.0541 0.5859 0.1124 0.050 Uiso 1 1 calc R . .
C11 C 0.1314(9) 0.4225(4) 0.1571(4) 0.0397(14) Uani 1 1 d . . .
C12 C 0.1324(8) 0.3333(4) 0.2392(4) 0.0331(13) Uani 1 1 d . . .
H12 H 0.1838 0.2618 0.2302 0.040 Uiso 1 1 calc R . .
C13 C 0.5933(7) 0.1452(3) 0.4308(4) 0.0228(11) Uani 1 1 d . . .
C14 C 0.5969(7) 0.2506(3) 0.3490(4) 0.0216(10) Uani 1 1 d . . .
C15 C 0.5137(8) 0.3513(4) 0.3741(4) 0.0290(12) Uani 1 1 d . . .
H15 H 0.4608 0.3520 0.4430 0.035 Uiso 1 1 calc R . .
C16 C 0.5797(9) 0.4459(4) 0.2057(5) 0.0437(15) Uani 1 1 d . . .
H16 H 0.5747 0.5120 0.1558 0.052 Uiso 1 1 calc R . .
C17 C 0.6633(9) 0.3487(4) 0.1760(4) 0.0399(14) Uani 1 1 d . . .
C18 C 0.6788(8) 0.2497(4) 0.2455(4) 0.0311(12) Uani 1 1 d . . .
H18 H 0.7411 0.1842 0.2252 0.037 Uiso 1 1 calc R . .
F1 F 0.9019(6) -0.2021(3) 1.0014(3) 0.0683(11) Uani 1 1 d . . .
F2 F 0.2106(7) 0.4064(3) 0.0611(2) 0.0712(13) Uani 1 1 d . . .
F3 F 0.7342(7) 0.3523(3) 0.0748(3) 0.0762(13) Uani 1 1 d . . .
H7W H 0.707(10) 0.367(5) 0.581(5) 0.04(2) Uiso 1 1 d . . .
H8W H 0.579(12) 0.435(6) 0.634(6) 0.10(3) 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
Gd1 O6 2.312(3) 2_656 ?
Gd1 O5 2.340(3) . ?
Gd1 O7 2.421(3) . ?
Gd1 O9 2.428(4) . ?
Gd1 O8 2.436(3) . ?
Gd1 O1 2.446(3) . ?
Gd1 O3 2.491(3) . ?
Gd1 O2 2.552(4) . ?
Gd1 O4 2.712(4) . ?
O1 C1 1.266(6) . ?
O2 C1 1.243(6) . ?
O3 C7 1.265(6) . ?
O4 C7 1.249(5) . ?
O5 C13 1.259(5) . ?
O6 C13 1.243(5) . ?
O6 Gd1 2.312(3) 2_656 ?
O7 H2W 0.9077 . ?
O7 H1W 0.8579 . ?
O8 H3W 0.8633 . ?
O8 H4W 0.8627 . ?
O9 H6W 0.8530 . ?
O9 H5W 0.8529 . ?
O10 H7W 0.73(6) . ?
O10 H8W 0.96(7) . ?
N1 C3 1.316(6) . ?
N1 C4 1.340(8) . ?
N2 C10 1.317(7) . ?
N2 C9 1.323(6) . ?
N3 C16 1.332(7) . ?
N3 C15 1.343(6) . ?
C1 C2 1.499(7) . ?
C2 C6 1.381(7) . ?
C2 C3 1.394(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.359(8) . ?
C4 H4 0.9300 . ?
C5 F1 1.349(6) . ?
C5 C6 1.376(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.497(6) . ?
C8 C12 1.381(7) . ?
C8 C9 1.392(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.363(7) . ?
C10 H10 0.9300 . ?
C11 F2 1.351(6) . ?
C11 C12 1.366(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.502(6) . ?
C14 C15 1.379(6) . ?
C14 C18 1.399(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.367(7) . ?
C16 H16 0.9300 . ?
C17 F3 1.348(6) . ?
C17 C18 1.359(7) . ?
C18 H18 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O6 Gd1 O5 82.90(11) 2_656 . ?
O6 Gd1 O7 143.93(13) 2_656 . ?
O5 Gd1 O7 73.45(11) . . ?
O6 Gd1 O9 70.49(12) 2_656 . ?
O5 Gd1 O9 140.02(12) . . ?
O7 Gd1 O9 142.77(12) . . ?
O6 Gd1 O8 135.81(12) 2_656 . ?
O5 Gd1 O8 141.29(11) . . ?
O7 Gd1 O8 71.85(13) . . ?
O9 Gd1 O8 71.01(12) . . ?
O6 Gd1 O1 84.18(12) 2_656 . ?
O5 Gd1 O1 124.09(12) . . ?
O7 Gd1 O1 86.96(12) . . ?
O9 Gd1 O1 83.19(13) . . ?
O8 Gd1 O1 70.49(12) . . ?
O6 Gd1 O3 130.44(12) 2_656 . ?
O5 Gd1 O3 85.70(12) . . ?
O7 Gd1 O3 75.23(12) . . ?
O9 Gd1 O3 89.40(13) . . ?
O8 Gd1 O3 69.37(11) . . ?
O1 Gd1 O3 139.41(11) . . ?
O6 Gd1 O2 75.77(12) 2_656 . ?
O5 Gd1 O2 71.78(11) . . ?
O7 Gd1 O2 71.21(12) . . ?
O9 Gd1 O2 126.17(12) . . ?
O8 Gd1 O2 111.71(12) . . ?
O1 Gd1 O2 52.32(11) . . ?
O3 Gd1 O2 143.63(12) . . ?
O6 Gd1 O4 81.28(11) 2_656 . ?
O5 Gd1 O4 69.67(12) . . ?
O7 Gd1 O4 113.99(11) . . ?
O9 Gd1 O4 77.06(12) . . ?
O8 Gd1 O4 110.14(12) . . ?
O1 Gd1 O4 158.49(12) . . ?
O3 Gd1 O4 49.68(10) . . ?
O2 Gd1 O4 137.01(11) . . ?
C1 O1 Gd1 94.5(3) . . ?
C1 O2 Gd1 90.1(3) . . ?
C7 O3 Gd1 98.3(3) . . ?
C7 O4 Gd1 88.3(3) . . ?
C13 O5 Gd1 143.3(3) . . ?
C13 O6 Gd1 166.8(3) . 2_656 ?
Gd1 O7 H2W 93.7 . . ?
Gd1 O7 H1W 109.3 . . ?
H2W O7 H1W 117.5 . . ?
Gd1 O8 H3W 110.0 . . ?
Gd1 O8 H4W 109.9 . . ?
H3W O8 H4W 108.8 . . ?
Gd1 O9 H6W 109.3 . . ?
Gd1 O9 H5W 109.2 . . ?
H6W O9 H5W 109.3 . . ?
H7W O10 H8W 102(6) . . ?
C3 N1 C4 117.8(5) . . ?
C10 N2 C9 118.1(4) . . ?
C16 N3 C15 117.6(4) . . ?
O2 C1 O1 123.1(5) . . ?
O2 C1 C2 119.3(5) . . ?
O1 C1 C2 117.6(4) . . ?
C6 C2 C3 118.3(5) . . ?
C6 C2 C1 121.5(5) . . ?
C3 C2 C1 120.2(5) . . ?
N1 C3 C2 123.8(5) . . ?
N1 C3 H3 118.1 . . ?
C2 C3 H3 118.1 . . ?
N1 C4 C5 121.5(5) . . ?
N1 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
F1 C5 C4 118.9(5) . . ?
F1 C5 C6 119.3(5) . . ?
C4 C5 C6 121.8(5) . . ?
C5 C6 C2 116.8(5) . . ?
C5 C6 H6 121.6 . . ?
C2 C6 H6 121.6 . . ?
O4 C7 O3 121.6(4) . . ?
O4 C7 C8 120.3(4) . . ?
O3 C7 C8 117.9(4) . . ?
C12 C8 C9 117.9(4) . . ?
C12 C8 C7 121.3(4) . . ?
C9 C8 C7 120.7(4) . . ?
N2 C9 C8 123.4(4) . . ?
N2 C9 H9 118.3 . . ?
C8 C9 H9 118.3 . . ?
N2 C10 C11 121.8(5) . . ?
N2 C10 H10 119.1 . . ?
C11 C10 H10 119.1 . . ?
F2 C11 C10 119.4(5) . . ?
F2 C11 C12 119.2(5) . . ?
C10 C11 C12 121.4(5) . . ?
C11 C12 C8 117.3(5) . . ?
C11 C12 H12 121.3 . . ?
C8 C12 H12 121.3 . . ?
O6 C13 O5 126.4(4) . . ?
O6 C13 C14 117.7(4) . . ?
O5 C13 C14 115.9(4) . . ?
C15 C14 C18 118.3(4) . . ?
C15 C14 C13 120.4(4) . . ?
C18 C14 C13 121.3(4) . . ?
N3 C15 C14 123.5(5) . . ?
N3 C15 H15 118.3 . . ?
C14 C15 H15 118.3 . . ?
N3 C16 C17 121.6(5) . . ?
N3 C16 H16 119.2 . . ?
C17 C16 H16 119.2 . . ?
F3 C17 C18 119.6(5) . . ?
F3 C17 C16 118.4(5) . . ?
C18 C17 C16 121.9(5) . . ?
C17 C18 C14 117.1(4) . . ?
C17 C18 H18 121.4 . . ?
C14 C18 H18 121.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O6 Gd1 O1 C1 75.2(3) 2_656 . . . ?
O5 Gd1 O1 C1 -2.1(3) . . . . ?
O7 Gd1 O1 C1 -69.7(3) . . . . ?
O9 Gd1 O1 C1 146.2(3) . . . . ?
O8 Gd1 O1 C1 -141.6(3) . . . . ?
O3 Gd1 O1 C1 -132.7(3) . . . . ?
O2 Gd1 O1 C1 -1.3(2) . . . . ?
O4 Gd1 O1 C1 122.9(4) . . . . ?
O6 Gd1 O2 C1 -92.4(3) 2_656 . . . ?
O5 Gd1 O2 C1 -179.5(3) . . . . ?
O7 Gd1 O2 C1 102.4(3) . . . . ?
O9 Gd1 O2 C1 -40.1(3) . . . . ?
O8 Gd1 O2 C1 41.7(3) . . . . ?
O1 Gd1 O2 C1 1.3(3) . . . . ?
O3 Gd1 O2 C1 126.0(3) . . . . ?
O4 Gd1 O2 C1 -152.3(2) . . . . ?
O6 Gd1 O3 C7 -18.1(4) 2_656 . . . ?
O5 Gd1 O3 C7 58.7(3) . . . . ?
O7 Gd1 O3 C7 132.7(3) . . . . ?
O9 Gd1 O3 C7 -81.5(3) . . . . ?
O8 Gd1 O3 C7 -151.4(3) . . . . ?
O1 Gd1 O3 C7 -160.3(3) . . . . ?
O2 Gd1 O3 C7 109.6(3) . . . . ?
O4 Gd1 O3 C7 -8.1(3) . . . . ?
O6 Gd1 O4 C7 -179.6(3) 2_656 . . . ?
O5 Gd1 O4 C7 -94.0(3) . . . . ?
O7 Gd1 O4 C7 -33.8(3) . . . . ?
O9 Gd1 O4 C7 108.5(3) . . . . ?
O8 Gd1 O4 C7 44.6(3) . . . . ?
O1 Gd1 O4 C7 132.4(3) . . . . ?
O3 Gd1 O4 C7 8.1(3) . . . . ?
O2 Gd1 O4 C7 -121.5(3) . . . . ?
O6 Gd1 O5 C13 48.8(5) 2_656 . . . ?
O7 Gd1 O5 C13 -158.7(5) . . . . ?
O9 Gd1 O5 C13 1.1(6) . . . . ?
O8 Gd1 O5 C13 -131.6(5) . . . . ?
O1 Gd1 O5 C13 126.9(5) . . . . ?
O3 Gd1 O5 C13 -82.8(5) . . . . ?
O2 Gd1 O5 C13 126.1(5) . . . . ?
O4 Gd1 O5 C13 -34.5(5) . . . . ?
Gd1 O2 C1 O1 -2.3(5) . . . . ?
Gd1 O2 C1 C2 176.5(4) . . . . ?
Gd1 O1 C1 O2 2.4(5) . . . . ?
Gd1 O1 C1 C2 -176.5(3) . . . . ?
O2 C1 C2 C6 -5.3(7) . . . . ?
O1 C1 C2 C6 173.7(4) . . . . ?
O2 C1 C2 C3 176.4(4) . . . . ?
O1 C1 C2 C3 -4.7(7) . . . . ?
C4 N1 C3 C2 -1.3(8) . . . . ?
C6 C2 C3 N1 0.9(8) . . . . ?
C1 C2 C3 N1 179.3(5) . . . . ?
C3 N1 C4 C5 0.2(8) . . . . ?
N1 C4 C5 F1 -179.5(5) . . . . ?
N1 C4 C5 C6 1.4(9) . . . . ?
F1 C5 C6 C2 179.2(4) . . . . ?
C4 C5 C6 C2 -1.8(8) . . . . ?
C3 C2 C6 C5 0.6(7) . . . . ?
C1 C2 C6 C5 -177.8(4) . . . . ?
Gd1 O4 C7 O3 -14.4(5) . . . . ?
Gd1 O4 C7 C8 161.8(4) . . . . ?
Gd1 O3 C7 O4 15.9(6) . . . . ?
Gd1 O3 C7 C8 -160.4(4) . . . . ?
O4 C7 C8 C12 -4.3(8) . . . . ?
O3 C7 C8 C12 172.1(5) . . . . ?
O4 C7 C8 C9 179.7(5) . . . . ?
O3 C7 C8 C9 -3.9(8) . . . . ?
C10 N2 C9 C8 -0.9(8) . . . . ?
C12 C8 C9 N2 0.2(8) . . . . ?
C7 C8 C9 N2 176.3(5) . . . . ?
C9 N2 C10 C11 0.6(9) . . . . ?
N2 C10 C11 F2 -179.3(6) . . . . ?
N2 C10 C11 C12 0.4(10) . . . . ?
F2 C11 C12 C8 178.6(5) . . . . ?
C10 C11 C12 C8 -1.1(9) . . . . ?
C9 C8 C12 C11 0.8(8) . . . . ?
C7 C8 C12 C11 -175.4(5) . . . . ?
Gd1 O6 C13 O5 61.0(16) 2_656 . . . ?
Gd1 O6 C13 C14 -119.8(12) 2_656 . . . ?
Gd1 O5 C13 O6 -72.2(7) . . . . ?
Gd1 O5 C13 C14 108.6(5) . . . . ?
O6 C13 C14 C15 -169.1(5) . . . . ?
O5 C13 C14 C15 10.2(7) . . . . ?
O6 C13 C14 C18 12.7(7) . . . . ?
O5 C13 C14 C18 -168.0(5) . . . . ?
C16 N3 C15 C14 0.7(8) . . . . ?
C18 C14 C15 N3 0.8(8) . . . . ?
C13 C14 C15 N3 -177.5(5) . . . . ?
C15 N3 C16 C17 -0.4(9) . . . . ?
N3 C16 C17 F3 179.4(6) . . . . ?
N3 C16 C17 C18 -1.4(10) . . . . ?
F3 C17 C18 C14 -178.1(5) . . . . ?
C16 C17 C18 C14 2.8(9) . . . . ?
C15 C14 C18 C17 -2.4(8) . . . . ?
C13 C14 C18 C17 175.8(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O7 H1W N2 0.86 2.05 2.828(5) 150.5 2_566
O8 H3W O10 0.86 2.20 2.806(6) 127.5 1_455
O8 H4W N1 0.86 2.22 2.750(6) 119.6 2_557
O9 H5W O2 0.85 2.31 2.848(5) 121.4 1_455
O9 H6W O4 0.85 2.23 2.824(5) 127.1 2_556
O10 H8W N3 0.96(7) 1.83(8) 2.774(6) 168(7) 2_666
O10 H7W O3 0.73(6) 2.17(6) 2.831(6) 151(6) 1_655

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.10
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         1.123
_refine_diff_density_min         -1.502
_refine_diff_density_rms         0.132
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_227-12tb
_database_code_depnum_ccdc_archive 'CCDC 1434385'
_audit_update_record             
;
2015-10-30 deposited with the CCDC.
2016-02-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H17 F3 N3 O10 Tb'
_chemical_formula_weight         651.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   6.7859(4)
_cell_length_b                   12.7748(7)
_cell_length_c                   13.5660(8)
_cell_angle_alpha                74.689(5)
_cell_angle_beta                 77.546(5)
_cell_angle_gamma                76.536(5)
_cell_volume                     1088.10(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.988
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             636
_exptl_absorpt_coefficient_mu    3.337
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4892
_exptl_absorpt_correction_T_max  0.5849
_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 APE-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7228
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_sigmaI/netI    0.0560
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.37
_diffrn_reflns_theta_max         25.05
_reflns_number_total             3831
_reflns_number_gt                3482
_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    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0179P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3831
_refine_ls_number_parameters     327
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0288
_refine_ls_wR_factor_ref         0.0621
_refine_ls_wR_factor_gt          0.0589
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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 0.68208(3) 0.115115(16) 0.626042(14) 0.01925(8) Uani 1 1 d . . .
O1 O 0.9781(5) 0.0336(3) 0.7288(2) 0.0358(8) Uani 1 1 d . . .
O2 O 0.6641(4) 0.0147(3) 0.8053(2) 0.0331(8) Uani 1 1 d . . .
O3 O 0.6313(5) 0.1645(3) 0.4229(3) 0.0406(8) Uani 1 1 d . . .
O4 O 0.5109(5) 0.2865(3) 0.5189(2) 0.0377(8) Uani 1 1 d . . .
O5 O 0.9833(4) 0.1532(2) 0.5172(2) 0.0287(7) Uani 1 1 d . . .
O6 O 1.1967(4) 0.0581(2) 0.4078(2) 0.0291(7) Uani 1 1 d . . .
O7 O 0.7724(5) 0.2605(3) 0.6794(2) 0.0386(8) Uani 1 1 d . . .
H1W H 0.6644 0.3101 0.6908 0.058 Uiso 1 1 d R . .
H2W H 0.8614 0.2915 0.6315 0.058 Uiso 1 1 d R . .
O8 O 0.3854(5) 0.2034(3) 0.7290(2) 0.0361(8) Uani 1 1 d . . .
H3W H 0.3498 0.1570 0.7849 0.054 Uiso 1 1 d R . .
H4W H 0.2854 0.2262 0.6947 0.054 Uiso 1 1 d R . .
O9 O 0.3953(4) 0.0320(3) 0.6289(2) 0.0378(8) Uani 1 1 d . . .
H5W H 0.3055 0.0393 0.6830 0.057 Uiso 1 1 d R . .
H6W H 0.4370 -0.0371 0.6300 0.057 Uiso 1 1 d R . .
O10 O 0.1117(6) 0.3636(3) 0.6141(4) 0.0468(10) Uani 1 1 d . . .
N1 N 0.8557(6) -0.1667(4) 1.0786(3) 0.0449(11) Uani 1 1 d . . .
N2 N 0.4754(6) 0.5479(3) 0.2633(3) 0.0363(10) Uani 1 1 d . . .
N3 N 1.0061(6) 0.4473(3) 0.3051(3) 0.0353(10) Uani 1 1 d . . .
C1 C 0.8557(7) -0.0020(4) 0.8056(3) 0.0266(10) Uani 1 1 d . . .
C2 C 0.9349(6) -0.0711(4) 0.9021(3) 0.0250(10) Uani 1 1 d . . .
C3 C 0.7998(7) -0.1051(4) 0.9898(3) 0.0374(12) Uani 1 1 d . . .
H3 H 0.6601 -0.0837 0.9869 0.045 Uiso 1 1 calc R . .
C4 C 1.0587(8) -0.1982(4) 1.0806(4) 0.0448(14) Uani 1 1 d . . .
H4 H 1.1038 -0.2417 1.1412 0.054 Uiso 1 1 calc R . .
C5 C 1.1989(7) -0.1676(4) 0.9956(4) 0.0371(12) Uani 1 1 d . . .
C6 C 1.1442(7) -0.1017(4) 0.9051(3) 0.0325(11) Uani 1 1 d . . .
H6 H 1.2415 -0.0786 0.8485 0.039 Uiso 1 1 calc R . .
C7 C 0.5633(6) 0.2604(4) 0.4319(4) 0.0298(11) Uani 1 1 d . . .
C8 C 0.5552(6) 0.3531(4) 0.3363(3) 0.0234(9) Uani 1 1 d . . .
C9 C 0.4786(6) 0.4619(4) 0.3435(3) 0.0295(10) Uani 1 1 d . . .
H9 H 0.4258 0.4755 0.4091 0.035 Uiso 1 1 calc R . .
C10 C 0.5528(7) 0.5282(4) 0.1700(4) 0.0406(12) Uani 1 1 d . . .
H10 H 0.5538 0.5870 0.1124 0.049 Uiso 1 1 calc R . .
C11 C 0.6315(8) 0.4223(4) 0.1570(3) 0.0376(12) Uani 1 1 d . . .
C12 C 0.6323(7) 0.3332(4) 0.2390(3) 0.0331(11) Uani 1 1 d . . .
H12 H 0.6830 0.2618 0.2295 0.040 Uiso 1 1 calc R . .
C13 C 1.0913(6) 0.1446(3) 0.4308(3) 0.0212(9) Uani 1 1 d . . .
C14 C 1.0957(6) 0.2499(3) 0.3490(3) 0.0215(9) Uani 1 1 d . . .
C15 C 1.0125(6) 0.3510(4) 0.3740(3) 0.0285(10) Uani 1 1 d . . .
H15 H 0.9580 0.3518 0.4429 0.034 Uiso 1 1 calc R . .
C16 C 1.0792(7) 0.4467(4) 0.2059(4) 0.0409(12) Uani 1 1 d . . .
H16 H 1.0724 0.5128 0.1562 0.049 Uiso 1 1 calc R . .
C17 C 1.1652(8) 0.3480(4) 0.1767(3) 0.0382(12) Uani 1 1 d . . .
C18 C 1.1784(7) 0.2486(4) 0.2465(3) 0.0319(11) Uani 1 1 d . . .
H18 H 1.2403 0.1830 0.2261 0.038 Uiso 1 1 calc R . .
F1 F 1.4015(4) -0.2024(3) 1.0030(3) 0.0683(10) Uani 1 1 d . . .
F2 F 0.7101(6) 0.4065(3) 0.0601(2) 0.0727(11) Uani 1 1 d . . .
F3 F 1.2352(6) 0.3518(3) 0.0749(2) 0.0762(11) Uani 1 1 d . . .
H7W H 0.220(10) 0.361(5) 0.558(5) 0.08(2) Uiso 1 1 d . . .
H8W H 0.075(9) 0.411(5) 0.639(5) 0.06(2) 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
Tb1 O6 2.304(3) 2_756 ?
Tb1 O5 2.319(3) . ?
Tb1 O7 2.404(3) . ?
Tb1 O9 2.413(3) . ?
Tb1 O8 2.417(3) . ?
Tb1 O2 2.423(3) . ?
Tb1 O4 2.473(3) . ?
Tb1 O1 2.555(3) . ?
Tb1 O3 2.739(3) . ?
O1 C1 1.239(5) . ?
O2 C1 1.268(5) . ?
O3 C7 1.233(5) . ?
O4 C7 1.266(5) . ?
O5 C13 1.258(5) . ?
O6 C13 1.244(5) . ?
O6 Tb1 2.304(3) 2_756 ?
O7 H1W 0.8662 . ?
O7 H2W 0.8661 . ?
O8 H3W 0.8571 . ?
O8 H4W 0.8572 . ?
O9 H5W 0.8588 . ?
O9 H6W 0.8587 . ?
O10 H7W 0.94(6) . ?
O10 H8W 0.74(5) . ?
N1 C3 1.332(6) . ?
N1 C4 1.346(6) . ?
N2 C10 1.326(6) . ?
N2 C9 1.326(6) . ?
N3 C16 1.331(6) . ?
N3 C15 1.332(6) . ?
C1 C2 1.501(6) . ?
C2 C3 1.374(6) . ?
C2 C6 1.389(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.361(7) . ?
C4 H4 0.9300 . ?
C5 F1 1.359(5) . ?
C5 C6 1.364(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.508(6) . ?
C8 C12 1.378(6) . ?
C8 C9 1.388(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.377(7) . ?
C10 H10 0.9300 . ?
C11 F2 1.357(5) . ?
C11 C12 1.365(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.503(6) . ?
C14 C15 1.383(6) . ?
C14 C18 1.386(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.381(7) . ?
C16 H16 0.9300 . ?
C17 F3 1.352(5) . ?
C17 C18 1.366(7) . ?
C18 H18 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O6 Tb1 O5 82.89(10) 2_756 . ?
O6 Tb1 O7 143.94(10) 2_756 . ?
O5 Tb1 O7 74.01(10) . . ?
O6 Tb1 O9 70.72(10) 2_756 . ?
O5 Tb1 O9 138.98(10) . . ?
O7 Tb1 O9 142.67(10) . . ?
O6 Tb1 O8 136.61(11) 2_756 . ?
O5 Tb1 O8 140.49(11) . . ?
O7 Tb1 O8 70.56(11) . . ?
O9 Tb1 O8 72.27(11) . . ?
O6 Tb1 O2 83.66(10) 2_756 . ?
O5 Tb1 O2 124.27(9) . . ?
O7 Tb1 O2 86.89(11) . . ?
O9 Tb1 O2 84.24(11) . . ?
O8 Tb1 O2 70.83(10) . . ?
O6 Tb1 O4 130.13(10) 2_756 . ?
O5 Tb1 O4 85.64(10) . . ?
O7 Tb1 O4 75.94(11) . . ?
O9 Tb1 O4 88.03(11) . . ?
O8 Tb1 O4 69.40(10) . . ?
O2 Tb1 O4 139.97(10) . . ?
O6 Tb1 O1 75.82(10) 2_756 . ?
O5 Tb1 O1 71.96(10) . . ?
O7 Tb1 O1 70.93(11) . . ?
O9 Tb1 O1 127.39(11) . . ?
O8 Tb1 O1 111.13(10) . . ?
O2 Tb1 O1 52.31(10) . . ?
O4 Tb1 O1 143.90(11) . . ?
O6 Tb1 O3 81.22(10) 2_756 . ?
O5 Tb1 O3 69.48(10) . . ?
O7 Tb1 O3 114.59(11) . . ?
O9 Tb1 O3 75.75(10) . . ?
O8 Tb1 O3 110.57(10) . . ?
O2 Tb1 O3 158.01(10) . . ?
O4 Tb1 O3 49.45(10) . . ?
O1 Tb1 O3 137.00(10) . . ?
C1 O1 Tb1 89.9(3) . . ?
C1 O2 Tb1 95.4(3) . . ?
C7 O3 Tb1 87.0(3) . . ?
C7 O4 Tb1 98.7(3) . . ?
C13 O5 Tb1 143.6(3) . . ?
C13 O6 Tb1 166.4(3) . 2_756 ?
Tb1 O7 H1W 110.2 . . ?
Tb1 O7 H2W 110.2 . . ?
H1W O7 H2W 108.7 . . ?
Tb1 O8 H3W 109.6 . . ?
Tb1 O8 H4W 109.6 . . ?
H3W O8 H4W 109.1 . . ?
Tb1 O9 H5W 109.9 . . ?
Tb1 O9 H6W 109.7 . . ?
H5W O9 H6W 109.0 . . ?
H7W O10 H8W 124(6) . . ?
C3 N1 C4 116.9(4) . . ?
C10 N2 C9 117.6(4) . . ?
C16 N3 C15 118.5(4) . . ?
O1 C1 O2 122.4(4) . . ?
O1 C1 C2 119.6(4) . . ?
O2 C1 C2 118.0(4) . . ?
C3 C2 C6 118.7(4) . . ?
C3 C2 C1 120.1(4) . . ?
C6 C2 C1 121.3(4) . . ?
N1 C3 C2 124.3(4) . . ?
N1 C3 H3 117.8 . . ?
C2 C3 H3 117.8 . . ?
N1 C4 C5 121.1(4) . . ?
N1 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
F1 C5 C4 118.0(4) . . ?
F1 C5 C6 119.3(5) . . ?
C4 C5 C6 122.7(4) . . ?
C5 C6 C2 116.2(4) . . ?
C5 C6 H6 121.9 . . ?
C2 C6 H6 121.9 . . ?
O3 C7 O4 122.7(4) . . ?
O3 C7 C8 119.7(4) . . ?
O4 C7 C8 117.4(4) . . ?
C12 C8 C9 117.6(4) . . ?
C12 C8 C7 121.1(4) . . ?
C9 C8 C7 121.2(4) . . ?
N2 C9 C8 124.4(4) . . ?
N2 C9 H9 117.8 . . ?
C8 C9 H9 117.8 . . ?
N2 C10 C11 121.2(4) . . ?
N2 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
F2 C11 C12 119.4(5) . . ?
F2 C11 C10 119.0(5) . . ?
C12 C11 C10 121.6(4) . . ?
C11 C12 C8 117.6(4) . . ?
C11 C12 H12 121.2 . . ?
C8 C12 H12 121.2 . . ?
O6 C13 O5 126.3(4) . . ?
O6 C13 C14 117.5(4) . . ?
O5 C13 C14 116.2(4) . . ?
C15 C14 C18 118.1(4) . . ?
C15 C14 C13 120.5(4) . . ?
C18 C14 C13 121.3(4) . . ?
N3 C15 C14 123.7(4) . . ?
N3 C15 H15 118.1 . . ?
C14 C15 H15 118.1 . . ?
N3 C16 C17 120.1(5) . . ?
N3 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
F3 C17 C18 119.8(4) . . ?
F3 C17 C16 117.9(4) . . ?
C18 C17 C16 122.3(4) . . ?
C17 C18 C14 117.1(4) . . ?
C17 C18 H18 121.4 . . ?
C14 C18 H18 121.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O6 Tb1 O1 C1 -92.1(3) 2_756 . . . ?
O5 Tb1 O1 C1 -179.1(3) . . . . ?
O7 Tb1 O1 C1 102.1(3) . . . . ?
O9 Tb1 O1 C1 -40.5(3) . . . . ?
O8 Tb1 O1 C1 42.8(3) . . . . ?
O2 Tb1 O1 C1 0.9(2) . . . . ?
O4 Tb1 O1 C1 126.5(3) . . . . ?
O3 Tb1 O1 C1 -152.0(2) . . . . ?
O6 Tb1 O2 C1 76.1(3) 2_756 . . . ?
O5 Tb1 O2 C1 -0.8(3) . . . . ?
O7 Tb1 O2 C1 -69.0(3) . . . . ?
O9 Tb1 O2 C1 147.3(3) . . . . ?
O8 Tb1 O2 C1 -139.5(3) . . . . ?
O4 Tb1 O2 C1 -132.7(2) . . . . ?
O1 Tb1 O2 C1 -0.8(2) . . . . ?
O3 Tb1 O2 C1 122.9(3) . . . . ?
O6 Tb1 O3 C7 179.9(3) 2_756 . . . ?
O5 Tb1 O3 C7 -94.4(3) . . . . ?
O7 Tb1 O3 C7 -34.1(3) . . . . ?
O9 Tb1 O3 C7 107.7(3) . . . . ?
O8 Tb1 O3 C7 43.3(3) . . . . ?
O2 Tb1 O3 C7 132.8(3) . . . . ?
O4 Tb1 O3 C7 7.9(2) . . . . ?
O1 Tb1 O3 C7 -122.0(3) . . . . ?
O6 Tb1 O4 C7 -18.1(3) 2_756 . . . ?
O5 Tb1 O4 C7 58.8(3) . . . . ?
O7 Tb1 O4 C7 133.4(3) . . . . ?
O9 Tb1 O4 C7 -80.6(3) . . . . ?
O8 Tb1 O4 C7 -152.4(3) . . . . ?
O2 Tb1 O4 C7 -159.3(2) . . . . ?
O1 Tb1 O4 C7 109.6(3) . . . . ?
O3 Tb1 O4 C7 -7.8(2) . . . . ?
O6 Tb1 O5 C13 49.2(5) 2_756 . . . ?
O7 Tb1 O5 C13 -158.7(5) . . . . ?
O9 Tb1 O5 C13 -0.2(5) . . . . ?
O8 Tb1 O5 C13 -131.8(4) . . . . ?
O2 Tb1 O5 C13 126.5(4) . . . . ?
O4 Tb1 O5 C13 -82.1(5) . . . . ?
O1 Tb1 O5 C13 126.6(5) . . . . ?
O3 Tb1 O5 C13 -34.0(4) . . . . ?
Tb1 O1 C1 O2 -1.5(4) . . . . ?
Tb1 O1 C1 C2 176.2(3) . . . . ?
Tb1 O2 C1 O1 1.6(5) . . . . ?
Tb1 O2 C1 C2 -176.1(3) . . . . ?
O1 C1 C2 C3 175.9(4) . . . . ?
O2 C1 C2 C3 -6.3(6) . . . . ?
O1 C1 C2 C6 -4.0(6) . . . . ?
O2 C1 C2 C6 173.8(4) . . . . ?
C4 N1 C3 C2 -1.0(8) . . . . ?
C6 C2 C3 N1 -0.4(7) . . . . ?
C1 C2 C3 N1 179.8(4) . . . . ?
C3 N1 C4 C5 0.4(8) . . . . ?
N1 C4 C5 F1 180.0(4) . . . . ?
N1 C4 C5 C6 1.7(8) . . . . ?
F1 C5 C6 C2 178.7(4) . . . . ?
C4 C5 C6 C2 -3.0(7) . . . . ?
C3 C2 C6 C5 2.3(6) . . . . ?
C1 C2 C6 C5 -177.8(4) . . . . ?
Tb1 O3 C7 O4 -14.1(4) . . . . ?
Tb1 O3 C7 C8 161.2(3) . . . . ?
Tb1 O4 C7 O3 15.8(5) . . . . ?
Tb1 O4 C7 C8 -159.6(3) . . . . ?
O3 C7 C8 C12 -3.3(6) . . . . ?
O4 C7 C8 C12 172.2(4) . . . . ?
O3 C7 C8 C9 179.6(4) . . . . ?
O4 C7 C8 C9 -4.8(6) . . . . ?
C10 N2 C9 C8 -0.7(7) . . . . ?
C12 C8 C9 N2 -0.3(6) . . . . ?
C7 C8 C9 N2 176.8(4) . . . . ?
C9 N2 C10 C11 0.7(7) . . . . ?
N2 C10 C11 F2 -179.6(4) . . . . ?
N2 C10 C11 C12 0.4(8) . . . . ?
F2 C11 C12 C8 178.6(4) . . . . ?
C10 C11 C12 C8 -1.4(7) . . . . ?
C9 C8 C12 C11 1.3(6) . . . . ?
C7 C8 C12 C11 -175.8(4) . . . . ?
Tb1 O6 C13 O5 61.4(13) 2_756 . . . ?
Tb1 O6 C13 C14 -120.1(11) 2_756 . . . ?
Tb1 O5 C13 O6 -72.8(6) . . . . ?
Tb1 O5 C13 C14 108.6(5) . . . . ?
O6 C13 C14 C15 -168.6(4) . . . . ?
O5 C13 C14 C15 10.1(5) . . . . ?
O6 C13 C14 C18 12.9(6) . . . . ?
O5 C13 C14 C18 -168.5(4) . . . . ?
C16 N3 C15 C14 1.6(7) . . . . ?
C18 C14 C15 N3 0.5(6) . . . . ?
C13 C14 C15 N3 -178.1(4) . . . . ?
C15 N3 C16 C17 -1.9(7) . . . . ?
N3 C16 C17 F3 179.3(4) . . . . ?
N3 C16 C17 C18 0.2(7) . . . . ?
F3 C17 C18 C14 -177.2(4) . . . . ?
C16 C17 C18 C14 1.9(7) . . . . ?
C15 C14 C18 C17 -2.2(6) . . . . ?
C13 C14 C18 C17 176.4(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O7 H1W N2 0.87 2.03 2.820(5) 151.3 2_666
O7 H2W O10 0.87 2.06 2.782(5) 140.7 1_655
O8 H3W N1 0.86 2.08 2.752(5) 135.2 2_657
O8 H4W O10 0.86 2.06 2.804(5) 144.7 .
O9 H5W O1 0.86 2.19 2.861(4) 135.2 1_455
O9 H6W O3 0.86 2.12 2.833(4) 140.2 2_656
O10 H7W O4 0.94(6) 2.00(6) 2.810(5) 143(5) .
O10 H8W N3 0.74(5) 2.05(6) 2.792(5) 174(7) 2_666

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.586
_refine_diff_density_min         -0.845
_refine_diff_density_rms         0.115
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_228-9tm1
_database_code_depnum_ccdc_archive 'CCDC 1434386'
_audit_update_record             
;
2015-10-30 deposited with the CCDC.
2016-02-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H19 F3 N3 O11 Tm'
_chemical_formula_weight         679.29

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Tm Tm -0.3139 5.2483 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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                   6.7196(4)
_cell_length_b                   13.0045(9)
_cell_length_c                   13.3399(9)
_cell_angle_alpha                94.604(6)
_cell_angle_beta                 93.382(5)
_cell_angle_gamma                102.228(5)
_cell_volume                     1132.13(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.993
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_absorpt_coefficient_mu    4.008
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4221
_exptl_absorpt_correction_T_max  0.5323
_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 APE-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7335
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_sigmaI/netI    0.0660
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.36
_diffrn_reflns_theta_max         25.05
_reflns_number_total             3982
_reflns_number_gt                3553
_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    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0214P)²+0.5429P] 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         3982
_refine_ls_number_parameters     332
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0364
_refine_ls_wR_factor_ref         0.0768
_refine_ls_wR_factor_gt          0.0713
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_restrained_S_all      1.107
_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
Tm1 Tm 0.51158(4) -0.08357(2) 0.657738(19) 0.01929(10) Uani 1 1 d . . .
N1 N 0.8922(8) 0.1636(5) 1.0835(4) 0.0341(14) Uani 1 1 d . . .
N2 N 0.8200(8) 0.4540(4) 0.6703(5) 0.0344(14) Uani 1 1 d . . .
N3 N 0.3706(9) 0.5693(5) 0.7402(5) 0.0453(16) Uani 1 1 d . . .
O1 O 0.5563(6) -0.0099(4) 0.8287(3) 0.0339(11) Uani 1 1 d . . .
O2 O 0.8360(6) -0.0245(3) 0.7562(3) 0.0299(10) Uani 1 1 d . . .
O3 O 0.6178(6) 0.0807(3) 0.6100(3) 0.0294(10) Uani 1 1 d . . .
O4 O 0.6747(6) 0.1770(3) 0.4807(3) 0.0292(10) Uani 1 1 d . . .
O5 O 0.7679(6) -0.0987(4) 0.5476(3) 0.0290(10) Uani 1 1 d . . .
H1W H 0.7844 -0.0478 0.5077 0.044 Uiso 1 1 d R . .
H2W H 0.7348 -0.1590 0.5101 0.044 Uiso 1 1 d R . .
O6 O 0.6064(6) -0.2415(3) 0.6855(3) 0.0339(11) Uani 1 1 d . . .
H3W H 0.5104 -0.2813 0.7120 0.051 Uiso 1 1 d R . .
H4W H 0.7141 -0.2286 0.7254 0.051 Uiso 1 1 d R . .
O7 O 0.2431(6) -0.1921(3) 0.7276(3) 0.0288(10) Uani 1 1 d . . .
H5W H 0.2785 -0.1995 0.7886 0.043 Uiso 1 1 d R . .
H6W H 0.2147 -0.2524 0.6936 0.043 Uiso 1 1 d R . .
O8 O 0.2283(6) -0.0004(3) 0.6514(3) 0.0347(11) Uani 1 1 d . . .
H7W H 0.1188 -0.0471 0.6352 0.052 Uiso 1 1 d R . .
H8W H 0.2437 0.0443 0.6075 0.052 Uiso 1 1 d R . .
O9 O 0.2231(8) 0.1963(4) 0.6921(4) 0.0491(13) Uani 1 1 d . . .
O10 O 0.2350(7) 0.2833(4) 0.5552(4) 0.0472(13) Uani 1 1 d . . .
O11 O 0.9223(8) 0.6657(4) 0.6231(4) 0.0430(13) Uani 1 1 d G . .
H9W H 0.9101 0.6011 0.6333 0.064 Uiso 1 1 d G . .
H10W H 0.8821 0.6702 0.5623 0.064 Uiso 1 1 d G . .
F1 F 1.3936(5) 0.2097(4) 0.9949(3) 0.0553(12) Uani 1 1 d . . .
F2 F 0.7664(8) 0.3489(4) 0.9101(3) 0.0727(15) Uani 1 1 d . . .
F3 F 0.2782(8) 0.4681(4) 0.9779(3) 0.0824(17) Uani 1 1 d . . .
C1 C 0.7508(9) 0.0088(5) 0.8290(5) 0.0244(14) Uani 1 1 d . . .
C2 C 0.8773(9) 0.0756(5) 0.9168(4) 0.0209(13) Uani 1 1 d . . .
C3 C 0.7878(9) 0.1052(5) 1.0032(5) 0.0289(15) Uani 1 1 d . . .
H3 H 0.6471 0.0829 1.0047 0.035 Uiso 1 1 calc R . .
C4 C 1.0938(10) 0.1973(5) 1.0784(5) 0.0340(16) Uani 1 1 d . . .
H4 H 1.1707 0.2392 1.1330 0.041 Uiso 1 1 calc R . .
C5 C 1.1900(9) 0.1717(6) 0.9946(5) 0.0337(17) Uani 1 1 d . . .
C6 C 1.0847(9) 0.1101(5) 0.9128(5) 0.0279(15) Uani 1 1 d . . .
H6 H 1.1505 0.0922 0.8567 0.033 Uiso 1 1 calc R . .
C7 C 0.6699(8) 0.1668(5) 0.5726(5) 0.0208(14) Uani 1 1 d . . .
C8 C 0.7232(8) 0.2650(5) 0.6446(4) 0.0194(13) Uani 1 1 d . . .
C9 C 0.7777(8) 0.3644(5) 0.6098(5) 0.0268(15) Uani 1 1 d . . .
H9 H 0.7850 0.3684 0.5408 0.032 Uiso 1 1 calc R . .
C10 C 0.8161(9) 0.4472(6) 0.7698(6) 0.0395(18) Uani 1 1 d . . .
H10 H 0.8480 0.5087 0.8136 0.047 Uiso 1 1 calc R . .
C11 C 0.7660(10) 0.3514(6) 0.8083(5) 0.0370(17) Uani 1 1 d . . .
C12 C 0.7168(9) 0.2594(5) 0.7478(5) 0.0293(15) Uani 1 1 d . . .
H12 H 0.6799 0.1948 0.7745 0.035 Uiso 1 1 calc R . .
C13 C 0.2414(9) 0.2776(5) 0.6480(5) 0.0295(16) Uani 1 1 d . . .
C14 C 0.2790(8) 0.3804(5) 0.7158(5) 0.0262(15) Uani 1 1 d . . .
C15 C 0.3340(9) 0.4803(6) 0.6807(5) 0.0354(17) Uani 1 1 d . . .
H15 H 0.3453 0.4840 0.6119 0.043 Uiso 1 1 calc R . .
C16 C 0.3506(11) 0.5638(6) 0.8383(6) 0.048(2) Uani 1 1 d . . .
H16 H 0.3726 0.6260 0.8810 0.058 Uiso 1 1 calc R . .
C17 C 0.2986(11) 0.4691(6) 0.8778(5) 0.0434(19) Uani 1 1 d . . .
C18 C 0.2621(9) 0.3760(5) 0.8178(5) 0.0355(17) Uani 1 1 d . . .
H18 H 0.2268 0.3115 0.8449 0.043 Uiso 1 1 calc 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
Tm1 O3 2.259(4) . ?
Tm1 O4 2.276(4) 2_656 ?
Tm1 O6 2.325(4) . ?
Tm1 O7 2.333(4) . ?
Tm1 O5 2.358(4) . ?
Tm1 O1 2.378(4) . ?
Tm1 O8 2.381(4) . ?
Tm1 O2 2.420(4) . ?
N1 C3 1.331(8) . ?
N1 C4 1.340(8) . ?
N2 C9 1.331(8) . ?
N2 C10 1.339(8) . ?
N3 C15 1.318(9) . ?
N3 C16 1.330(9) . ?
O1 C1 1.277(7) . ?
O2 C1 1.250(7) . ?
O3 C7 1.253(6) . ?
O4 C7 1.245(7) . ?
O4 Tm1 2.276(4) 2_656 ?
O5 H1W 0.8753 . ?
O5 H2W 0.8743 . ?
O6 H3W 0.8511 . ?
O6 H4W 0.8508 . ?
O7 H5W 0.8526 . ?
O7 H6W 0.8526 . ?
O8 H7W 0.8532 . ?
O8 H8W 0.8536 . ?
O9 C13 1.239(7) . ?
O10 C13 1.244(7) . ?
O11 H9W 0.8501 . ?
O11 H10W 0.8502 . ?
F1 C5 1.352(7) . ?
F2 C11 1.362(7) . ?
F3 C17 1.351(8) . ?
C1 C2 1.501(8) . ?
C2 C6 1.377(8) . ?
C2 C3 1.395(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(10) . ?
C4 H4 0.9300 . ?
C5 C6 1.364(9) . ?
C6 H6 0.9300 . ?
C7 C8 1.500(8) . ?
C8 C12 1.387(8) . ?
C8 C9 1.391(8) . ?
C9 H9 0.9300 . ?
C10 C11 1.369(9) . ?
C10 H10 0.9300 . ?
C11 C12 1.356(9) . ?
C12 H12 0.9300 . ?
C13 C14 1.519(9) . ?
C14 C18 1.376(9) . ?
C14 C15 1.399(8) . ?
C15 H15 0.9300 . ?
C16 C17 1.365(10) . ?
C16 H16 0.9300 . ?
C17 C18 1.365(10) . ?
C18 H18 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 Tm1 O4 104.39(15) . 2_656 ?
O3 Tm1 O6 145.02(15) . . ?
O4 Tm1 O6 84.98(15) 2_656 . ?
O3 Tm1 O7 142.91(15) . . ?
O4 Tm1 O7 77.30(15) 2_656 . ?
O6 Tm1 O7 71.75(14) . . ?
O3 Tm1 O5 75.16(15) . . ?
O4 Tm1 O5 78.23(14) 2_656 . ?
O6 Tm1 O5 73.96(15) . . ?
O7 Tm1 O5 139.14(16) . . ?
O3 Tm1 O1 88.94(16) . . ?
O4 Tm1 O1 153.80(14) 2_656 . ?
O6 Tm1 O1 97.00(16) . . ?
O7 Tm1 O1 78.56(15) . . ?
O5 Tm1 O1 127.52(14) . . ?
O3 Tm1 O8 71.53(14) . . ?
O4 Tm1 O8 79.81(16) 2_656 . ?
O6 Tm1 O8 143.32(15) . . ?
O7 Tm1 O8 72.41(14) . . ?
O5 Tm1 O8 133.62(15) . . ?
O1 Tm1 O8 83.35(15) . . ?
O3 Tm1 O2 78.40(14) . . ?
O4 Tm1 O2 149.53(15) 2_656 . ?
O6 Tm1 O2 77.29(15) . . ?
O7 Tm1 O2 118.98(14) . . ?
O5 Tm1 O2 73.17(14) . . ?
O1 Tm1 O2 54.57(14) . . ?
O8 Tm1 O2 128.27(16) . . ?
C3 N1 C4 117.1(6) . . ?
C9 N2 C10 117.8(6) . . ?
C15 N3 C16 118.3(6) . . ?
C1 O1 Tm1 92.5(4) . . ?
C1 O2 Tm1 91.3(4) . . ?
C7 O3 Tm1 172.9(4) . . ?
C7 O4 Tm1 132.6(4) . 2_656 ?
Tm1 O5 H1W 111.0 . . ?
Tm1 O5 H2W 110.3 . . ?
H1W O5 H2W 108.1 . . ?
Tm1 O6 H3W 109.1 . . ?
Tm1 O6 H4W 109.3 . . ?
H3W O6 H4W 109.4 . . ?
Tm1 O7 H5W 109.8 . . ?
Tm1 O7 H6W 108.8 . . ?
H5W O7 H6W 109.3 . . ?
Tm1 O8 H7W 109.3 . . ?
Tm1 O8 H8W 109.5 . . ?
H7W O8 H8W 109.3 . . ?
H9W O11 H10W 109.5 . . ?
O2 C1 O1 121.0(6) . . ?
O2 C1 C2 119.9(5) . . ?
O1 C1 C2 119.0(6) . . ?
C6 C2 C3 118.6(6) . . ?
C6 C2 C1 120.4(6) . . ?
C3 C2 C1 121.1(5) . . ?
N1 C3 C2 123.7(6) . . ?
N1 C3 H3 118.1 . . ?
C2 C3 H3 118.1 . . ?
N1 C4 C5 121.7(6) . . ?
N1 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
F1 C5 C6 120.2(6) . . ?
F1 C5 C4 118.2(6) . . ?
C6 C5 C4 121.6(6) . . ?
C5 C6 C2 117.3(6) . . ?
C5 C6 H6 121.3 . . ?
C2 C6 H6 121.3 . . ?
O4 C7 O3 125.0(6) . . ?
O4 C7 C8 117.9(5) . . ?
O3 C7 C8 117.0(5) . . ?
C12 C8 C9 118.1(6) . . ?
C12 C8 C7 120.9(5) . . ?
C9 C8 C7 121.0(5) . . ?
N2 C9 C8 123.3(6) . . ?
N2 C9 H9 118.3 . . ?
C8 C9 H9 118.3 . . ?
N2 C10 C11 121.3(7) . . ?
N2 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
C12 C11 F2 119.4(6) . . ?
C12 C11 C10 121.8(6) . . ?
F2 C11 C10 118.9(7) . . ?
C11 C12 C8 117.7(6) . . ?
C11 C12 H12 121.2 . . ?
C8 C12 H12 121.2 . . ?
O9 C13 O10 126.9(7) . . ?
O9 C13 C14 115.5(6) . . ?
O10 C13 C14 117.6(6) . . ?
C18 C14 C15 117.7(7) . . ?
C18 C14 C13 118.7(6) . . ?
C15 C14 C13 123.6(6) . . ?
N3 C15 C14 123.4(7) . . ?
N3 C15 H15 118.3 . . ?
C14 C15 H15 118.3 . . ?
N3 C16 C17 121.5(7) . . ?
N3 C16 H16 119.3 . . ?
C17 C16 H16 119.3 . . ?
F3 C17 C16 119.0(7) . . ?
F3 C17 C18 119.7(7) . . ?
C16 C17 C18 121.2(7) . . ?
C17 C18 C14 118.0(6) . . ?
C17 C18 H18 121.0 . . ?
C14 C18 H18 121.0 . . ?

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
O3 Tm1 O1 C1 -72.2(3) . . . . ?
O4 Tm1 O1 C1 166.1(3) 2_656 . . . ?
O6 Tm1 O1 C1 73.2(4) . . . . ?
O7 Tm1 O1 C1 142.9(4) . . . . ?
O5 Tm1 O1 C1 -1.9(4) . . . . ?
O8 Tm1 O1 C1 -143.8(4) . . . . ?
O2 Tm1 O1 C1 4.3(3) . . . . ?
O3 Tm1 O2 C1 92.7(4) . . . . ?
O4 Tm1 O2 C1 -168.6(3) 2_656 . . . ?
O6 Tm1 O2 C1 -112.6(4) . . . . ?
O7 Tm1 O2 C1 -52.1(4) . . . . ?
O5 Tm1 O2 C1 170.5(4) . . . . ?
O1 Tm1 O2 C1 -4.4(3) . . . . ?
O8 Tm1 O2 C1 37.7(4) . . . . ?
O4 Tm1 O3 C7 -13(3) 2_656 . . . ?
O6 Tm1 O3 C7 89(3) . . . . ?
O7 Tm1 O3 C7 -101(3) . . . . ?
O5 Tm1 O3 C7 60(3) . . . . ?
O1 Tm1 O3 C7 -170(3) . . . . ?
O8 Tm1 O3 C7 -87(3) . . . . ?
O2 Tm1 O3 C7 136(3) . . . . ?
Tm1 O2 C1 O1 7.7(6) . . . . ?
Tm1 O2 C1 C2 -169.7(4) . . . . ?
Tm1 O1 C1 O2 -7.9(6) . . . . ?
Tm1 O1 C1 C2 169.6(4) . . . . ?
O2 C1 C2 C6 7.1(8) . . . . ?
O1 C1 C2 C6 -170.4(5) . . . . ?
O2 C1 C2 C3 -173.8(5) . . . . ?
O1 C1 C2 C3 8.7(8) . . . . ?
C4 N1 C3 C2 1.9(9) . . . . ?
C6 C2 C3 N1 -1.4(9) . . . . ?
C1 C2 C3 N1 179.5(5) . . . . ?
C3 N1 C4 C5 -0.9(10) . . . . ?
N1 C4 C5 F1 179.3(6) . . . . ?
N1 C4 C5 C6 -0.4(10) . . . . ?
F1 C5 C6 C2 -178.9(5) . . . . ?
C4 C5 C6 C2 0.9(9) . . . . ?
C3 C2 C6 C5 0.0(8) . . . . ?
C1 C2 C6 C5 179.1(5) . . . . ?
Tm1 O4 C7 O3 30.5(9) 2_656 . . . ?
Tm1 O4 C7 C8 -147.3(4) 2_656 . . . ?
Tm1 O3 C7 O4 -9(4) . . . . ?
Tm1 O3 C7 C8 168(3) . . . . ?
O4 C7 C8 C12 178.7(5) . . . . ?
O3 C7 C8 C12 0.7(8) . . . . ?
O4 C7 C8 C9 -0.4(8) . . . . ?
O3 C7 C8 C9 -178.4(5) . . . . ?
C10 N2 C9 C8 2.3(9) . . . . ?
C12 C8 C9 N2 -1.3(9) . . . . ?
C7 C8 C9 N2 177.8(5) . . . . ?
C9 N2 C10 C11 -1.4(9) . . . . ?
N2 C10 C11 C12 -0.5(10) . . . . ?
N2 C10 C11 F2 179.4(6) . . . . ?
F2 C11 C12 C8 -178.4(6) . . . . ?
C10 C11 C12 C8 1.5(10) . . . . ?
C9 C8 C12 C11 -0.6(8) . . . . ?
C7 C8 C12 C11 -179.7(5) . . . . ?
O9 C13 C14 C18 -8.8(8) . . . . ?
O10 C13 C14 C18 172.1(6) . . . . ?
O9 C13 C14 C15 170.0(6) . . . . ?
O10 C13 C14 C15 -9.0(9) . . . . ?
C16 N3 C15 C14 -1.3(10) . . . . ?
C18 C14 C15 N3 0.3(9) . . . . ?
C13 C14 C15 N3 -178.6(6) . . . . ?
C15 N3 C16 C17 1.6(11) . . . . ?
N3 C16 C17 F3 -179.3(6) . . . . ?
N3 C16 C17 C18 -1.0(11) . . . . ?
F3 C17 C18 C14 178.2(6) . . . . ?
C16 C17 C18 C14 -0.1(10) . . . . ?
C15 C14 C18 C17 0.4(9) . . . . ?
C13 C14 C18 C17 179.3(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O5 H1W O8 0.88 2.26 3.043(6) 148.2 2_656
O5 H2W O10 0.87 1.83 2.664(7) 158.7 2_656
O6 H3W N3 0.85 2.05 2.806(7) 148.3 1_545
O7 H5W N1 0.85 2.19 2.753(7) 123.9 2_657
O7 H6W O11 0.85 2.15 2.748(6) 127.2 1_445
O8 H7W O2 0.85 2.61 3.025(6) 111.0 1_455
O8 H8W O5 0.85 2.24 3.043(6) 156.2 2_656
O11 H9W N2 0.85 1.99 2.824(7) 166.5 .
O11 H10W O10 0.85 1.91 2.733(6) 162.3 2_666

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.689
_refine_diff_density_min         -0.682
_refine_diff_density_rms         0.150
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_233-9eu2
_database_code_depnum_ccdc_archive 'CCDC 1434387'
_audit_update_record             
;
2015-10-30 deposited with the CCDC.
2016-02-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H28 Eu F2 N7 O10'
_chemical_formula_weight         908.61

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'
F F 0.0171 0.0103 '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                   8.6142(2)
_cell_length_b                   27.4686(9)
_cell_length_c                   15.3524(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.233(3)
_cell_angle_gamma                90.00
_cell_volume                     3574.89(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.688
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1816
_exptl_absorpt_coefficient_mu    1.835
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6570
_exptl_absorpt_correction_T_max  0.6993
_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 APE-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14575
_diffrn_reflns_av_R_equivalents  0.0509
_diffrn_reflns_av_sigmaI/netI    0.0748
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.26
_diffrn_reflns_theta_max         25.05
_reflns_number_total             6318
_reflns_number_gt                4590
_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    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0480P)²+3.7938P] 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         6318
_refine_ls_number_parameters     509
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0709
_refine_ls_R_factor_gt           0.0470
_refine_ls_wR_factor_ref         0.1255
_refine_ls_wR_factor_gt          0.1078
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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
Eu1 Eu 0.32818(3) 0.375732(12) 0.763479(19) 0.03399(13) Uani 1 1 d . . .
N1 N 0.2565(12) 0.4518(4) 0.4063(7) 0.128(4) Uani 1 1 d . . .
N2 N 0.1888(9) 0.3365(3) 1.1663(4) 0.075(2) Uani 1 1 d . . .
N3 N 0.3744(6) 0.3480(2) 0.6055(3) 0.0412(14) Uani 1 1 d . . .
N4 N 0.1130(6) 0.3198(2) 0.6666(3) 0.0418(14) Uani 1 1 d . . .
N5 N 0.5063(6) 0.3882(2) 0.9265(3) 0.0424(14) Uani 1 1 d . . .
N6 N 0.2735(6) 0.4527(2) 0.8575(3) 0.0404(13) Uani 1 1 d . . .
N7 N 0.5418(7) 0.2899(3) 0.7945(4) 0.0518(16) Uani 1 1 d . . .
O1 O 0.1724(6) 0.42631(19) 0.6623(3) 0.0576(14) Uani 1 1 d . . .
O2 O -0.0874(7) 0.4240(3) 0.6093(4) 0.111(3) Uani 1 1 d . . .
O3 O 0.1580(5) 0.35431(17) 0.8561(3) 0.0410(11) Uani 1 1 d . . .
O4 O -0.0350(6) 0.3837(2) 0.9190(3) 0.0641(16) Uani 1 1 d . . .
O5 O 0.5148(5) 0.43498(18) 0.7330(3) 0.0530(13) Uani 1 1 d . . .
H1W H 0.5198 0.4352 0.6771 0.079 Uiso 1 1 d R . .
H2W H 0.6073 0.4280 0.7626 0.079 Uiso 1 1 d R . .
O6 O 0.3987(5) 0.28908(18) 0.8061(3) 0.0501(12) Uani 1 1 d . . .
O7 O 0.5911(5) 0.3299(2) 0.7690(3) 0.0510(12) Uani 1 1 d . . .
O8 O 0.6278(6) 0.2537(2) 0.8095(4) 0.0693(16) Uani 1 1 d . . .
O9 O 0.8204(5) 0.4309(2) 0.7686(3) 0.0695(16) Uani 1 1 d G . .
H3W H 0.8653 0.4165 0.8154 0.083 Uiso 1 1 d R . .
H4W H 0.8492 0.4291 0.7185 0.083 Uiso 1 1 d R . .
O10 O 0.480(2) 0.5248(4) 0.6326(9) 0.367(13) Uani 1 1 d . . .
H5W H 0.5681 0.5329 0.6195 0.440 Uiso 1 1 d R . .
H6W H 0.4889 0.4985 0.6423 0.440 Uiso 1 1 d R . .
F1 F -0.1103(15) 0.4069(6) 0.2859(7) 0.297(7) Uani 1 1 d . . .
F2 F 0.4840(5) 0.25889(18) 1.1018(3) 0.0739(13) Uani 1 1 d . . .
C1 C 0.0552(11) 0.4277(3) 0.6011(5) 0.068(2) Uani 1 1 d . . .
C2 C 0.0822(10) 0.4350(3) 0.5090(5) 0.066(2) Uani 1 1 d . . .
C3 C 0.2271(12) 0.4485(4) 0.4909(6) 0.090(3) Uani 1 1 d . . .
H3 H 0.3080 0.4557 0.5379 0.108 Uiso 1 1 calc R . .
C4 C 0.1466(16) 0.4410(6) 0.3392(8) 0.133(5) Uani 1 1 d . . .
H4 H 0.1667 0.4430 0.2817 0.160 Uiso 1 1 calc R . .
C5 C 0.0029(15) 0.4268(5) 0.3539(6) 0.116(5) Uani 1 1 d . . .
C6 C -0.0373(13) 0.4237(4) 0.4374(6) 0.102(4) Uani 1 1 d . . .
H6 H -0.1379 0.4147 0.4453 0.122 Uiso 1 1 calc R . .
C7 C 0.0900(7) 0.3613(2) 0.9220(4) 0.0388(16) Uani 1 1 d . . .
C8 C 0.1690(8) 0.3396(2) 1.0077(4) 0.0414(16) Uani 1 1 d . . .
C9 C 0.1233(9) 0.3529(3) 1.0873(5) 0.0547(19) Uani 1 1 d . . .
H9 H 0.0404 0.3749 1.0844 0.066 Uiso 1 1 calc R . .
C10 C 0.3082(11) 0.3047(3) 1.1687(5) 0.070(2) Uani 1 1 d . . .
H10 H 0.3572 0.2921 1.2229 0.084 Uiso 1 1 calc R . .
C11 C 0.3593(8) 0.2903(3) 1.0933(5) 0.0498(18) Uani 1 1 d . . .
C12 C 0.2901(7) 0.3064(3) 1.0110(4) 0.0412(16) Uani 1 1 d . . .
H12 H 0.3231 0.2954 0.9600 0.049 Uiso 1 1 calc R . .
C13 C 0.5061(8) 0.3594(3) 0.5761(5) 0.0532(19) Uani 1 1 d . . .
H13 H 0.5894 0.3726 0.6160 0.064 Uiso 1 1 calc R . .
C14 C 0.5260(10) 0.3527(4) 0.4888(5) 0.075(3) Uani 1 1 d . . .
H14 H 0.6200 0.3614 0.4711 0.090 Uiso 1 1 calc R . .
C15 C 0.4055(10) 0.3332(4) 0.4300(5) 0.075(3) Uani 1 1 d . . .
H15 H 0.4157 0.3288 0.3712 0.090 Uiso 1 1 calc R . .
C16 C 0.2680(9) 0.3199(3) 0.4579(5) 0.0537(19) Uani 1 1 d . . .
C17 C 0.2561(7) 0.3275(3) 0.5467(4) 0.0423(17) Uani 1 1 d . . .
C18 C 0.1351(10) 0.2988(3) 0.3991(5) 0.069(2) Uani 1 1 d . . .
H18 H 0.1391 0.2953 0.3393 0.083 Uiso 1 1 calc R . .
C19 C 0.0066(9) 0.2845(3) 0.4297(4) 0.061(2) Uani 1 1 d . . .
H19 H -0.0761 0.2703 0.3908 0.073 Uiso 1 1 calc R . .
C20 C -0.0069(7) 0.2903(3) 0.5200(4) 0.0445(17) Uani 1 1 d . . .
C21 C 0.1163(7) 0.3129(2) 0.5796(4) 0.0386(15) Uani 1 1 d . . .
C22 C -0.1404(8) 0.2743(3) 0.5548(5) 0.057(2) Uani 1 1 d . . .
H22 H -0.2244 0.2591 0.5185 0.068 Uiso 1 1 calc R . .
C23 C -0.1435(8) 0.2816(3) 0.6416(5) 0.064(2) Uani 1 1 d . . .
H23 H -0.2300 0.2716 0.6656 0.077 Uiso 1 1 calc R . .
C24 C -0.0162(8) 0.3041(3) 0.6944(5) 0.060(2) Uani 1 1 d . . .
H24 H -0.0214 0.3086 0.7539 0.072 Uiso 1 1 calc R . .
C25 C 0.6238(7) 0.3596(3) 0.9619(5) 0.0469(18) Uani 1 1 d . . .
H25 H 0.6695 0.3401 0.9238 0.056 Uiso 1 1 calc R . .
C26 C 0.6851(8) 0.3563(3) 1.0524(5) 0.059(2) Uani 1 1 d . . .
H26 H 0.7680 0.3352 1.0733 0.071 Uiso 1 1 calc R . .
C27 C 0.6201(8) 0.3846(3) 1.1085(5) 0.055(2) Uani 1 1 d . . .
H27 H 0.6553 0.3822 1.1692 0.066 Uiso 1 1 calc R . .
C28 C 0.5010(8) 0.4172(3) 1.0757(4) 0.0476(18) Uani 1 1 d . . .
C29 C 0.4446(7) 0.4186(3) 0.9823(4) 0.0407(16) Uani 1 1 d . . .
C30 C 0.4344(10) 0.4501(3) 1.1312(5) 0.062(2) Uani 1 1 d . . .
H30 H 0.4678 0.4489 1.1922 0.074 Uiso 1 1 calc R . .
C31 C 0.3247(9) 0.4827(3) 1.0967(5) 0.059(2) Uani 1 1 d . . .
H31 H 0.2842 0.5040 1.1341 0.071 Uiso 1 1 calc R . .
C32 C 0.2693(8) 0.4853(3) 1.0038(5) 0.0469(18) Uani 1 1 d . . .
C33 C 0.3250(7) 0.4528(2) 0.9462(4) 0.0389(16) Uani 1 1 d . . .
C34 C 0.1568(8) 0.5201(3) 0.9654(6) 0.057(2) Uani 1 1 d . . .
H34 H 0.1169 0.5425 1.0011 0.068 Uiso 1 1 calc R . .
C35 C 0.1074(8) 0.5208(3) 0.8771(5) 0.056(2) Uani 1 1 d . . .
H35 H 0.0342 0.5438 0.8511 0.067 Uiso 1 1 calc R . .
C36 C 0.1686(8) 0.4862(3) 0.8251(5) 0.0551(19) Uani 1 1 d . . .
H36 H 0.1335 0.4869 0.7642 0.066 Uiso 1 1 calc 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 O3 2.293(4) . ?
Eu1 O1 2.324(5) . ?
Eu1 O5 2.392(4) . ?
Eu1 O6 2.514(5) . ?
Eu1 O7 2.579(4) . ?
Eu1 N3 2.639(5) . ?
Eu1 N6 2.649(5) . ?
Eu1 N4 2.652(5) . ?
Eu1 N5 2.715(5) . ?
Eu1 H1W 2.8151 . ?
Eu1 H2W 2.8030 . ?
N1 C4 1.304(13) . ?
N1 C3 1.370(12) . ?
N2 C9 1.323(9) . ?
N2 C10 1.346(10) . ?
N3 C13 1.331(8) . ?
N3 C17 1.357(8) . ?
N4 C24 1.332(8) . ?
N4 C21 1.354(8) . ?
N5 C25 1.319(8) . ?
N5 C29 1.370(8) . ?
N6 C36 1.324(9) . ?
N6 C33 1.354(8) . ?
N7 O8 1.237(7) . ?
N7 O7 1.265(8) . ?
N7 O6 1.277(7) . ?
O1 C1 1.252(9) . ?
O2 C1 1.261(10) . ?
O3 C7 1.271(7) . ?
O4 C7 1.233(7) . ?
O5 H1W 0.8662 . ?
O5 H2W 0.8656 . ?
O9 H3W 0.8500 . ?
O9 H4W 0.8508 . ?
O10 H5W 0.8521 . ?
O10 H6W 0.7382 . ?
F1 C5 1.407(14) . ?
F2 C11 1.366(8) . ?
C1 C2 1.487(10) . ?
C2 C3 1.377(12) . ?
C2 C6 1.401(12) . ?
C3 H3 0.9300 . ?
C4 C5 1.354(16) . ?
C4 H4 0.9300 . ?
C5 C6 1.387(13) . ?
C6 H6 0.9300 . ?
C7 C8 1.494(9) . ?
C8 C12 1.380(9) . ?
C8 C9 1.397(9) . ?
C9 H9 0.9300 . ?
C10 C11 1.367(10) . ?
C10 H10 0.9300 . ?
C11 C12 1.371(9) . ?
C12 H12 0.9300 . ?
C13 C14 1.394(10) . ?
C13 H13 0.9300 . ?
C14 C15 1.359(11) . ?
C14 H14 0.9300 . ?
C15 C16 1.378(10) . ?
C15 H15 0.9300 . ?
C16 C17 1.401(9) . ?
C16 C18 1.447(10) . ?
C17 C21 1.443(9) . ?
C18 C19 1.336(10) . ?
C18 H18 0.9300 . ?
C19 C20 1.420(9) . ?
C19 H19 0.9300 . ?
C20 C21 1.416(9) . ?
C20 C22 1.421(9) . ?
C22 C23 1.352(10) . ?
C22 H22 0.9300 . ?
C23 C24 1.388(9) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 C26 1.398(10) . ?
C25 H25 0.9300 . ?
C26 C27 1.355(11) . ?
C26 H26 0.9300 . ?
C27 C28 1.387(10) . ?
C27 H27 0.9300 . ?
C28 C30 1.429(10) . ?
C28 C29 1.431(9) . ?
C29 C33 1.432(9) . ?
C30 C31 1.341(11) . ?
C30 H30 0.9300 . ?
C31 C32 1.423(10) . ?
C31 H31 0.9300 . ?
C32 C33 1.399(9) . ?
C32 C34 1.414(10) . ?
C34 C35 1.347(10) . ?
C34 H34 0.9300 . ?
C35 C36 1.402(9) . ?
C35 H35 0.9300 . ?
C36 H36 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 Eu1 O1 102.17(16) . . ?
O3 Eu1 O5 145.29(16) . . ?
O1 Eu1 O5 77.93(18) . . ?
O3 Eu1 O6 75.34(15) . . ?
O1 Eu1 O6 145.48(17) . . ?
O5 Eu1 O6 123.75(15) . . ?
O3 Eu1 O7 120.58(16) . . ?
O1 Eu1 O7 135.50(16) . . ?
O5 Eu1 O7 73.83(17) . . ?
O6 Eu1 O7 50.18(15) . . ?
O3 Eu1 N3 135.48(16) . . ?
O1 Eu1 N3 73.88(17) . . ?
O5 Eu1 N3 78.50(16) . . ?
O6 Eu1 N3 84.07(16) . . ?
O7 Eu1 N3 67.32(16) . . ?
O3 Eu1 N6 70.83(16) . . ?
O1 Eu1 N6 75.51(17) . . ?
O5 Eu1 N6 75.78(16) . . ?
O6 Eu1 N6 132.18(16) . . ?
O7 Eu1 N6 127.69(16) . . ?
N3 Eu1 N6 143.33(17) . . ?
O3 Eu1 N4 74.88(15) . . ?
O1 Eu1 N4 73.04(18) . . ?
O5 Eu1 N4 135.38(16) . . ?
O6 Eu1 N4 73.14(16) . . ?
O7 Eu1 N4 104.96(16) . . ?
N3 Eu1 N4 61.40(15) . . ?
N6 Eu1 N4 126.45(16) . . ?
O3 Eu1 N5 77.26(15) . . ?
O1 Eu1 N5 134.86(17) . . ?
O5 Eu1 N5 78.77(16) . . ?
O6 Eu1 N5 78.94(17) . . ?
O7 Eu1 N5 71.43(16) . . ?
N3 Eu1 N5 136.94(16) . . ?
N6 Eu1 N5 61.52(17) . . ?
N4 Eu1 N5 144.54(17) . . ?
O3 Eu1 H1W 159.0 . . ?
O1 Eu1 H1W 69.9 . . ?
O5 Eu1 H1W 16.7 . . ?
O6 Eu1 H1W 122.5 . . ?
O7 Eu1 H1W 73.3 . . ?
N3 Eu1 H1W 62.5 . . ?
N6 Eu1 H1W 88.3 . . ?
N4 Eu1 H1W 118.8 . . ?
N5 Eu1 H1W 94.5 . . ?
O3 Eu1 H2W 141.1 . . ?
O1 Eu1 H2W 94.8 . . ?
O5 Eu1 H2W 16.9 . . ?
O6 Eu1 H2W 108.6 . . ?
O7 Eu1 H2W 60.1 . . ?
N3 Eu1 H2W 82.8 . . ?
N6 Eu1 H2W 80.2 . . ?
N4 Eu1 H2W 144.0 . . ?
N5 Eu1 H2W 66.1 . . ?
H1W Eu1 H2W 29.0 . . ?
C4 N1 C3 120.3(11) . . ?
C9 N2 C10 116.4(7) . . ?
C13 N3 C17 117.2(6) . . ?
C13 N3 Eu1 121.3(5) . . ?
C17 N3 Eu1 120.9(4) . . ?
C24 N4 C21 115.9(6) . . ?
C24 N4 Eu1 123.2(4) . . ?
C21 N4 Eu1 120.0(4) . . ?
C25 N5 C29 117.4(6) . . ?
C25 N5 Eu1 124.9(4) . . ?
C29 N5 Eu1 115.7(4) . . ?
C36 N6 C33 117.1(6) . . ?
C36 N6 Eu1 121.7(4) . . ?
C33 N6 Eu1 119.5(4) . . ?
O8 N7 O7 122.2(6) . . ?
O8 N7 O6 121.4(7) . . ?
O7 N7 O6 116.4(6) . . ?
C1 O1 Eu1 144.4(6) . . ?
C7 O3 Eu1 153.0(4) . . ?
Eu1 O5 H1W 110.6 . . ?
Eu1 O5 H2W 109.6 . . ?
H1W O5 H2W 108.5 . . ?
N7 O6 Eu1 98.1(4) . . ?
N7 O7 Eu1 95.3(4) . . ?
H3W O9 H4W 125.2 . . ?
H5W O10 H6W 103.5 . . ?
O1 C1 O2 126.3(8) . . ?
O1 C1 C2 118.5(8) . . ?
O2 C1 C2 115.2(8) . . ?
C3 C2 C6 117.9(9) . . ?
C3 C2 C1 121.9(8) . . ?
C6 C2 C1 120.0(9) . . ?
N1 C3 C2 122.4(10) . . ?
N1 C3 H3 118.8 . . ?
C2 C3 H3 118.8 . . ?
N1 C4 C5 119.3(12) . . ?
N1 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C4 C5 C6 123.9(10) . . ?
C4 C5 F1 121.4(12) . . ?
C6 C5 F1 114.0(12) . . ?
C5 C6 C2 116.2(10) . . ?
C5 C6 H6 121.9 . . ?
C2 C6 H6 121.9 . . ?
O4 C7 O3 124.7(6) . . ?
O4 C7 C8 119.3(6) . . ?
O3 C7 C8 116.0(6) . . ?
C12 C8 C9 117.9(7) . . ?
C12 C8 C7 121.3(6) . . ?
C9 C8 C7 120.7(6) . . ?
N2 C9 C8 125.0(7) . . ?
N2 C9 H9 117.5 . . ?
C8 C9 H9 117.5 . . ?
N2 C10 C11 121.6(7) . . ?
N2 C10 H10 119.2 . . ?
C11 C10 H10 119.2 . . ?
C10 C11 F2 117.9(7) . . ?
C10 C11 C12 122.3(7) . . ?
F2 C11 C12 119.8(6) . . ?
C11 C12 C8 116.7(6) . . ?
C11 C12 H12 121.6 . . ?
C8 C12 H12 121.6 . . ?
N3 C13 C14 123.6(7) . . ?
N3 C13 H13 118.2 . . ?
C14 C13 H13 118.2 . . ?
C15 C14 C13 118.7(7) . . ?
C15 C14 H14 120.6 . . ?
C13 C14 H14 120.6 . . ?
C14 C15 C16 119.7(7) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C15 C16 C17 118.6(7) . . ?
C15 C16 C18 122.7(7) . . ?
C17 C16 C18 118.7(6) . . ?
N3 C17 C16 122.2(6) . . ?
N3 C17 C21 117.2(5) . . ?
C16 C17 C21 120.6(6) . . ?
C19 C18 C16 120.8(7) . . ?
C19 C18 H18 119.6 . . ?
C16 C18 H18 119.6 . . ?
C18 C19 C20 121.8(7) . . ?
C18 C19 H19 119.1 . . ?
C20 C19 H19 119.1 . . ?
C21 C20 C22 117.1(6) . . ?
C21 C20 C19 119.8(6) . . ?
C22 C20 C19 123.0(6) . . ?
N4 C21 C20 123.6(6) . . ?
N4 C21 C17 118.1(6) . . ?
C20 C21 C17 118.2(6) . . ?
C23 C22 C20 119.0(7) . . ?
C23 C22 H22 120.5 . . ?
C20 C22 H22 120.5 . . ?
C22 C23 C24 119.3(7) . . ?
C22 C23 H23 120.3 . . ?
C24 C23 H23 120.3 . . ?
N4 C24 C23 125.1(7) . . ?
N4 C24 H24 117.5 . . ?
C23 C24 H24 117.5 . . ?
N5 C25 C26 125.1(7) . . ?
N5 C25 H25 117.5 . . ?
C26 C25 H25 117.5 . . ?
C27 C26 C25 118.0(7) . . ?
C27 C26 H26 121.0 . . ?
C25 C26 H26 121.0 . . ?
C26 C27 C28 120.2(7) . . ?
C26 C27 H27 119.9 . . ?
C28 C27 H27 119.9 . . ?
C27 C28 C30 122.7(7) . . ?
C27 C28 C29 118.6(7) . . ?
C30 C28 C29 118.7(7) . . ?
N5 C29 C33 119.4(6) . . ?
N5 C29 C28 120.7(6) . . ?
C33 C29 C28 119.9(6) . . ?
C31 C30 C28 121.1(7) . . ?
C31 C30 H30 119.4 . . ?
C28 C30 H30 119.4 . . ?
C30 C31 C32 121.0(7) . . ?
C30 C31 H31 119.5 . . ?
C32 C31 H31 119.5 . . ?
C33 C32 C34 117.0(6) . . ?
C33 C32 C31 120.7(7) . . ?
C34 C32 C31 122.3(7) . . ?
N6 C33 C32 123.3(6) . . ?
N6 C33 C29 118.2(6) . . ?
C32 C33 C29 118.5(6) . . ?
C35 C34 C32 120.1(7) . . ?
C35 C34 H34 120.0 . . ?
C32 C34 H34 120.0 . . ?
C34 C35 C36 118.6(7) . . ?
C34 C35 H35 120.7 . . ?
C36 C35 H35 120.7 . . ?
N6 C36 C35 123.9(7) . . ?
N6 C36 H36 118.0 . . ?
C35 C36 H36 118.0 . . ?

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
O3 Eu1 N3 C13 -164.6(5) . . . . ?
O1 Eu1 N3 C13 104.3(6) . . . . ?
O5 Eu1 N3 C13 23.7(6) . . . . ?
O6 Eu1 N3 C13 -102.6(6) . . . . ?
O7 Eu1 N3 C13 -53.4(6) . . . . ?
N6 Eu1 N3 C13 69.8(6) . . . . ?
N4 Eu1 N3 C13 -176.6(6) . . . . ?
N5 Eu1 N3 C13 -35.7(7) . . . . ?
O3 Eu1 N3 C17 24.8(6) . . . . ?
O1 Eu1 N3 C17 -66.3(5) . . . . ?
O5 Eu1 N3 C17 -146.9(5) . . . . ?
O6 Eu1 N3 C17 86.8(5) . . . . ?
O7 Eu1 N3 C17 135.9(6) . . . . ?
N6 Eu1 N3 C17 -100.8(5) . . . . ?
N4 Eu1 N3 C17 12.8(5) . . . . ?
N5 Eu1 N3 C17 153.6(5) . . . . ?
O3 Eu1 N4 C24 7.2(6) . . . . ?
O1 Eu1 N4 C24 -100.9(6) . . . . ?
O5 Eu1 N4 C24 -152.6(5) . . . . ?
O6 Eu1 N4 C24 86.1(6) . . . . ?
O7 Eu1 N4 C24 125.4(6) . . . . ?
N3 Eu1 N4 C24 178.5(6) . . . . ?
N6 Eu1 N4 C24 -44.3(6) . . . . ?
N5 Eu1 N4 C24 46.5(7) . . . . ?
O3 Eu1 N4 C21 175.5(5) . . . . ?
O1 Eu1 N4 C21 67.4(5) . . . . ?
O5 Eu1 N4 C21 15.7(6) . . . . ?
O6 Eu1 N4 C21 -105.5(5) . . . . ?
O7 Eu1 N4 C21 -66.2(5) . . . . ?
N3 Eu1 N4 C21 -13.1(5) . . . . ?
N6 Eu1 N4 C21 124.0(5) . . . . ?
N5 Eu1 N4 C21 -145.1(4) . . . . ?
O3 Eu1 N5 C25 107.9(6) . . . . ?
O1 Eu1 N5 C25 -157.5(5) . . . . ?
O5 Eu1 N5 C25 -97.4(5) . . . . ?
O6 Eu1 N5 C25 30.6(5) . . . . ?
O7 Eu1 N5 C25 -20.9(5) . . . . ?
N3 Eu1 N5 C25 -38.1(6) . . . . ?
N6 Eu1 N5 C25 -177.2(6) . . . . ?
N4 Eu1 N5 C25 69.0(6) . . . . ?
O3 Eu1 N5 C29 -55.5(4) . . . . ?
O1 Eu1 N5 C29 39.1(5) . . . . ?
O5 Eu1 N5 C29 99.2(5) . . . . ?
O6 Eu1 N5 C29 -132.8(4) . . . . ?
O7 Eu1 N5 C29 175.7(5) . . . . ?
N3 Eu1 N5 C29 158.5(4) . . . . ?
N6 Eu1 N5 C29 19.4(4) . . . . ?
N4 Eu1 N5 C29 -94.4(5) . . . . ?
O3 Eu1 N6 C36 -98.3(5) . . . . ?
O1 Eu1 N6 C36 10.4(5) . . . . ?
O5 Eu1 N6 C36 91.4(5) . . . . ?
O6 Eu1 N6 C36 -145.7(5) . . . . ?
O7 Eu1 N6 C36 147.4(5) . . . . ?
N3 Eu1 N6 C36 44.6(6) . . . . ?
N4 Eu1 N6 C36 -45.2(6) . . . . ?
N5 Eu1 N6 C36 176.1(6) . . . . ?
O3 Eu1 N6 C33 66.4(4) . . . . ?
O1 Eu1 N6 C33 175.1(5) . . . . ?
O5 Eu1 N6 C33 -104.0(4) . . . . ?
O6 Eu1 N6 C33 19.0(5) . . . . ?
O7 Eu1 N6 C33 -47.9(5) . . . . ?
N3 Eu1 N6 C33 -150.8(4) . . . . ?
N4 Eu1 N6 C33 119.5(4) . . . . ?
N5 Eu1 N6 C33 -19.2(4) . . . . ?
O3 Eu1 O1 C1 -67.6(8) . . . . ?
O5 Eu1 O1 C1 147.9(9) . . . . ?
O6 Eu1 O1 C1 14.1(10) . . . . ?
O7 Eu1 O1 C1 96.5(9) . . . . ?
N3 Eu1 O1 C1 66.6(8) . . . . ?
N6 Eu1 O1 C1 -133.9(8) . . . . ?
N4 Eu1 O1 C1 2.2(8) . . . . ?
N5 Eu1 O1 C1 -151.7(8) . . . . ?
O1 Eu1 O3 C7 -84.8(9) . . . . ?
O5 Eu1 O3 C7 1.5(11) . . . . ?
O6 Eu1 O3 C7 130.6(9) . . . . ?
O7 Eu1 O3 C7 108.1(9) . . . . ?
N3 Eu1 O3 C7 -164.1(9) . . . . ?
N6 Eu1 O3 C7 -15.1(9) . . . . ?
N4 Eu1 O3 C7 -153.3(10) . . . . ?
N5 Eu1 O3 C7 48.9(9) . . . . ?
O8 N7 O6 Eu1 178.8(5) . . . . ?
O7 N7 O6 Eu1 0.4(6) . . . . ?
O3 Eu1 O6 N7 -154.8(4) . . . . ?
O1 Eu1 O6 N7 115.0(4) . . . . ?
O5 Eu1 O6 N7 -6.9(4) . . . . ?
O7 Eu1 O6 N7 -0.2(3) . . . . ?
N3 Eu1 O6 N7 65.1(4) . . . . ?
N6 Eu1 O6 N7 -108.8(4) . . . . ?
N4 Eu1 O6 N7 126.9(4) . . . . ?
N5 Eu1 O6 N7 -75.2(4) . . . . ?
O8 N7 O7 Eu1 -178.8(5) . . . . ?
O6 N7 O7 Eu1 -0.4(6) . . . . ?
O3 Eu1 O7 N7 29.1(4) . . . . ?
O1 Eu1 O7 N7 -132.8(4) . . . . ?
O5 Eu1 O7 N7 174.5(4) . . . . ?
O6 Eu1 O7 N7 0.2(3) . . . . ?
N3 Eu1 O7 N7 -101.5(4) . . . . ?
N6 Eu1 O7 N7 117.7(4) . . . . ?
N4 Eu1 O7 N7 -51.9(4) . . . . ?
N5 Eu1 O7 N7 91.2(4) . . . . ?
Eu1 O1 C1 O2 72.7(13) . . . . ?
Eu1 O1 C1 C2 -108.0(10) . . . . ?
O1 C1 C2 C3 -11.6(14) . . . . ?
O2 C1 C2 C3 167.8(9) . . . . ?
O1 C1 C2 C6 162.6(9) . . . . ?
O2 C1 C2 C6 -18.0(14) . . . . ?
C4 N1 C3 C2 -1(2) . . . . ?
C6 C2 C3 N1 0.7(17) . . . . ?
C1 C2 C3 N1 175.0(10) . . . . ?
C3 N1 C4 C5 0(2) . . . . ?
N1 C4 C5 C6 1(2) . . . . ?
N1 C4 C5 F1 -168.9(14) . . . . ?
C4 C5 C6 C2 -2(2) . . . . ?
F1 C5 C6 C2 169.0(12) . . . . ?
C3 C2 C6 C5 0.7(16) . . . . ?
C1 C2 C6 C5 -173.7(10) . . . . ?
Eu1 O3 C7 O4 88.8(11) . . . . ?
Eu1 O3 C7 C8 -92.4(10) . . . . ?
O4 C7 C8 C12 166.8(7) . . . . ?
O3 C7 C8 C12 -12.1(10) . . . . ?
O4 C7 C8 C9 -13.9(10) . . . . ?
O3 C7 C8 C9 167.2(6) . . . . ?
C10 N2 C9 C8 -0.2(13) . . . . ?
C12 C8 C9 N2 1.1(12) . . . . ?
C7 C8 C9 N2 -178.2(7) . . . . ?
C9 N2 C10 C11 0.4(13) . . . . ?
N2 C10 C11 F2 178.2(8) . . . . ?
N2 C10 C11 C12 -1.6(13) . . . . ?
C10 C11 C12 C8 2.5(11) . . . . ?
F2 C11 C12 C8 -177.3(6) . . . . ?
C9 C8 C12 C11 -2.1(10) . . . . ?
C7 C8 C12 C11 177.2(6) . . . . ?
C17 N3 C13 C14 1.8(12) . . . . ?
Eu1 N3 C13 C14 -169.2(7) . . . . ?
N3 C13 C14 C15 -0.4(15) . . . . ?
C13 C14 C15 C16 -0.9(15) . . . . ?
C14 C15 C16 C17 0.6(14) . . . . ?
C14 C15 C16 C18 -179.8(9) . . . . ?
C13 N3 C17 C16 -2.0(11) . . . . ?
Eu1 N3 C17 C16 169.0(5) . . . . ?
C13 N3 C17 C21 177.0(6) . . . . ?
Eu1 N3 C17 C21 -12.0(8) . . . . ?
C15 C16 C17 N3 0.9(12) . . . . ?
C18 C16 C17 N3 -178.7(7) . . . . ?
C15 C16 C17 C21 -178.1(8) . . . . ?
C18 C16 C17 C21 2.3(11) . . . . ?
C15 C16 C18 C19 176.9(9) . . . . ?
C17 C16 C18 C19 -3.5(13) . . . . ?
C16 C18 C19 C20 1.6(14) . . . . ?
C18 C19 C20 C21 1.6(12) . . . . ?
C18 C19 C20 C22 -178.5(8) . . . . ?
C24 N4 C21 C20 -0.3(10) . . . . ?
Eu1 N4 C21 C20 -169.5(5) . . . . ?
C24 N4 C21 C17 -177.7(7) . . . . ?
Eu1 N4 C21 C17 13.2(8) . . . . ?
C22 C20 C21 N4 0.1(11) . . . . ?
C19 C20 C21 N4 -180.0(7) . . . . ?
C22 C20 C21 C17 177.4(6) . . . . ?
C19 C20 C21 C17 -2.6(10) . . . . ?
N3 C17 C21 N4 -0.9(10) . . . . ?
C16 C17 C21 N4 178.1(7) . . . . ?
N3 C17 C21 C20 -178.3(6) . . . . ?
C16 C17 C21 C20 0.7(10) . . . . ?
C21 C20 C22 C23 0.3(11) . . . . ?
C19 C20 C22 C23 -179.7(8) . . . . ?
C20 C22 C23 C24 -0.4(13) . . . . ?
C21 N4 C24 C23 0.2(12) . . . . ?
Eu1 N4 C24 C23 169.0(7) . . . . ?
C22 C23 C24 N4 0.1(14) . . . . ?
C29 N5 C25 C26 3.2(11) . . . . ?
Eu1 N5 C25 C26 -159.9(6) . . . . ?
N5 C25 C26 C27 -0.3(12) . . . . ?
C25 C26 C27 C28 -2.7(11) . . . . ?
C26 C27 C28 C30 -176.1(7) . . . . ?
C26 C27 C28 C29 2.7(11) . . . . ?
C25 N5 C29 C33 175.3(6) . . . . ?
Eu1 N5 C29 C33 -20.0(7) . . . . ?
C25 N5 C29 C28 -3.1(9) . . . . ?
Eu1 N5 C29 C28 161.6(5) . . . . ?
C27 C28 C29 N5 0.3(10) . . . . ?
C30 C28 C29 N5 179.1(6) . . . . ?
C27 C28 C29 C33 -178.2(6) . . . . ?
C30 C28 C29 C33 0.7(9) . . . . ?
C27 C28 C30 C31 176.8(7) . . . . ?
C29 C28 C30 C31 -2.0(11) . . . . ?
C28 C30 C31 C32 0.8(12) . . . . ?
C30 C31 C32 C33 1.8(11) . . . . ?
C30 C31 C32 C34 -178.3(7) . . . . ?
C36 N6 C33 C32 2.1(9) . . . . ?
Eu1 N6 C33 C32 -163.3(5) . . . . ?
C36 N6 C33 C29 -176.8(6) . . . . ?
Eu1 N6 C33 C29 17.9(7) . . . . ?
C34 C32 C33 N6 -1.8(9) . . . . ?
C31 C32 C33 N6 178.2(6) . . . . ?
C34 C32 C33 C29 177.1(6) . . . . ?
C31 C32 C33 C29 -3.0(9) . . . . ?
N5 C29 C33 N6 2.2(9) . . . . ?
C28 C29 C33 N6 -179.4(6) . . . . ?
N5 C29 C33 C32 -176.7(5) . . . . ?
C28 C29 C33 C32 1.8(9) . . . . ?
C33 C32 C34 C35 0.4(10) . . . . ?
C31 C32 C34 C35 -179.6(7) . . . . ?
C32 C34 C35 C36 0.6(11) . . . . ?
C33 N6 C36 C35 -1.0(10) . . . . ?
Eu1 N6 C36 C35 164.0(5) . . . . ?
C34 C35 C36 N6 -0.3(11) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O10 H6W O5 0.74 2.22 2.895(13) 152.9 .
O10 H5W N1 0.85 1.68 2.53(2) 179.4 3_666
O9 H4W O2 0.85 1.86 2.709(8) 178.9 1_655
O9 H3W O4 0.85 1.90 2.746(7) 179.2 1_655
O5 H2W O9 0.87 1.82 2.595(6) 147.3 .

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.100
_refine_diff_density_min         -0.843
_refine_diff_density_rms         0.107
