# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_Z8-Tb-14R2
_database_code_depnum_ccdc_archive 'CCDC 1506104'
_audit_update_record             
;
2017-03-03 deposited with the CCDC.
2017-03-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H15 N3 O17 Tb2'
_chemical_formula_weight         815.13

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Tb Tb -0.1723 4.1537 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   9.4916(3)
_cell_length_b                   22.4131(7)
_cell_length_c                   10.1084(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.5000(10)
_cell_angle_gamma                90
_cell_volume                     2099.45(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9913
_cell_measurement_theta_min      2.82
_cell_measurement_theta_max      28.33

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.579
_exptl_crystal_F_000             1544
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    6.779
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3684
_exptl_absorpt_correction_T_max  0.4694
_exptl_absorpt_process_details   'SADABS (Bruker, 2000)'

_exptl_special_details           ?

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17215
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.820
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4120
_reflns_number_gt                3688
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0155P)²+5.1583P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4120
_refine_ls_number_parameters     326
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0247
_refine_ls_R_factor_gt           0.0195
_refine_ls_wR_factor_ref         0.0441
_refine_ls_wR_factor_gt          0.0424
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.061
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Tb1 Tb 0.71840(2) 0.43434(2) 0.85995(2) 0.01280(5) Uani 1 1 d . . . . .
Tb2 Tb 1.24869(2) 0.27656(2) 1.04949(2) 0.01455(5) Uani 1 1 d . . . . .
N1 N 0.5995(3) 0.41505(13) 0.6261(3) 0.0146(6) Uani 1 1 d . . . . .
N2 N 0.5327(3) 0.41333(14) 0.4047(3) 0.0174(7) Uani 1 1 d . . . . .
H2 H 0.527228 0.422563 0.321185 0.021 Uiso 1 1 calc R U . . .
N3 N 0.7750(4) 0.50784(15) 0.6461(4) 0.0253(8) Uani 1 1 d . . . . .
O1 O 1.0664(3) 0.33749(13) 1.1113(3) 0.0249(6) Uani 1 1 d . . . . .
O2 O 1.0312(3) 0.28688(12) 0.8683(3) 0.0249(6) Uani 1 1 d . . . . .
O3 O 0.8295(3) 0.34106(12) 0.7966(3) 0.0242(6) Uani 1 1 d . . . . .
O4 O 0.8507(3) 0.38060(13) 1.0504(3) 0.0261(7) Uani 1 1 d . . . . .
O5 O 0.5230(3) 0.36048(12) 0.8218(2) 0.0197(6) Uani 1 1 d . . . . .
O6 O 0.3794(3) 0.29552(12) 0.6935(3) 0.0223(6) Uani 1 1 d . . . . .
O7 O 0.2756(3) 0.29407(12) 0.3928(3) 0.0201(6) Uani 1 1 d . . . . .
O8 O 0.3663(3) 0.33668(12) 0.2310(3) 0.0211(6) Uani 1 1 d . . . . .
O9 O 0.6017(3) 0.43646(12) 1.0521(3) 0.0214(6) Uani 1 1 d . . . . .
O10 O 0.4690(3) 0.49137(12) 1.1634(3) 0.0199(6) Uani 1 1 d . . . . .
O11 O 0.9760(3) 0.44801(12) 0.8697(3) 0.0215(6) Uani 1 1 d . . . . .
O12 O 1.1785(3) 0.48189(12) 1.0020(3) 0.0239(6) Uani 1 1 d . . . . .
O13 O 1.2754(3) 0.36878(12) 0.9349(3) 0.0286(7) Uani 1 1 d . . . . .
H13A H 1.240628 0.400974 0.950473 0.043 Uiso 1 1 d R U . . .
H13B H 1.350456 0.376404 0.910799 0.043 Uiso 1 1 d R U . . .
O14 O 1.5035(3) 0.28355(13) 1.0310(3) 0.0304(7) Uani 1 1 d . . . . .
H14A H 1.564064 0.293534 1.097499 0.046 Uiso 1 1 d R U . . .
H14B H 1.520074 0.301567 0.965522 0.046 Uiso 1 1 d R U . . .
O15 O 1.0809(3) 0.20924(13) 1.1110(3) 0.0301(7) Uani 1 1 d . . . . .
H15A H 0.998691 0.215917 1.068010 0.045 Uiso 1 1 d R U . . .
H15B H 1.076581 0.207073 1.191292 0.045 Uiso 1 1 d R U . . .
O16 O 0.7281(6) 0.1733(3) 0.7549(5) 0.0990(17) Uani 1 1 d . U . . .
O17 O 0.7827(5) 0.2137(2) 0.0278(5) 0.0765(14) Uani 1 1 d . . . . .
C1 C 0.4550(4) 0.36906(16) 0.4507(4) 0.0148(7) Uani 1 1 d . . . . .
C2 C 0.4990(4) 0.37105(16) 0.5901(4) 0.0138(7) Uani 1 1 d . . . . .
C3 C 0.6184(4) 0.43977(16) 0.5119(4) 0.0158(8) Uani 1 1 d . . . . .
C4 C 0.7215(4) 0.48878(17) 0.5174(4) 0.0183(8) Uani 1 1 d . . . . .
C5 C 0.7635(5) 0.5123(2) 0.4055(5) 0.0325(10) Uani 1 1 d . . . . .
H5 H 0.727468 0.497151 0.319082 0.039 Uiso 1 1 calc R U . . .
C6 C 0.8617(6) 0.5595(2) 0.4265(5) 0.0416(12) Uani 1 1 d . . . . .
H6 H 0.892272 0.576871 0.354013 0.050 Uiso 1 1 calc R U . . .
C7 C 0.9125(6) 0.5799(2) 0.5565(6) 0.0422(13) Uani 1 1 d . . . . .
H7 H 0.976018 0.611977 0.572681 0.051 Uiso 1 1 calc R U . . .
C8 C 0.8690(5) 0.5525(2) 0.6615(5) 0.0341(11) Uani 1 1 d . . . . .
H8 H 0.907322 0.566007 0.748955 0.041 Uiso 1 1 calc R U . . .
C9 C 0.3572(4) 0.33021(16) 0.3520(4) 0.0150(8) Uani 1 1 d . . . . .
C10 C 0.4620(4) 0.33872(16) 0.7068(4) 0.0143(8) Uani 1 1 d . . . . .
C11 C 0.5202(4) 0.47895(16) 1.0617(3) 0.0151(8) Uani 1 1 d . . . . .
C12 C 1.0442(4) 0.47999(16) 0.9620(4) 0.0172(8) Uani 1 1 d . . . . .
C13 C 0.9526(4) 0.34885(17) 1.0292(4) 0.0207(8) Uani 1 1 d . . . . .
C14 C 0.9351(4) 0.32319(17) 0.8844(4) 0.0200(8) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Tb1 O4 2.385(3) . ?
Tb1 O10 2.410(3) 3_667 ?
Tb1 O12 2.416(3) 3_767 ?
Tb1 N1 2.428(3) . ?
Tb1 O9 2.436(3) . ?
Tb1 O11 2.444(3) . ?
Tb1 O5 2.454(3) . ?
Tb1 O3 2.487(3) . ?
Tb1 N3 2.860(4) . ?
Tb2 O7 2.293(3) 4_666 ?
Tb2 O6 2.342(3) 4_666 ?
Tb2 O8 2.354(3) 1_656 ?
Tb2 O15 2.373(3) . ?
Tb2 O1 2.391(3) . ?
Tb2 O13 2.409(3) . ?
Tb2 O2 2.456(3) . ?
Tb2 O14 2.470(3) . ?
N1 C3 1.327(4) . ?
N1 C2 1.365(5) . ?
N2 C3 1.344(5) . ?
N2 C1 1.376(5) . ?
N2 H2 0.8600 . ?
N3 C8 1.328(6) . ?
N3 C4 1.359(5) . ?
O1 C13 1.238(5) . ?
O2 C14 1.259(5) . ?
O3 C14 1.253(5) . ?
O4 C13 1.256(5) . ?
O5 C10 1.278(4) . ?
O6 C10 1.235(4) . ?
O7 C9 1.251(4) . ?
O8 C9 1.253(4) . ?
O9 C11 1.244(4) . ?
O10 C11 1.260(4) . ?
O11 C12 1.241(5) . ?
O12 C12 1.252(5) . ?
O13 H13A 0.8228 . ?
O13 H13B 0.8194 . ?
O14 H14A 0.8157 . ?
O14 H14B 0.8193 . ?
O15 H15A 0.8208 . ?
O15 H15B 0.8224 . ?
C1 C2 1.381(5) . ?
C1 C9 1.488(5) . ?
C2 C10 1.489(5) . ?
C3 C4 1.464(5) . ?
C4 C5 1.383(6) . ?
C5 C6 1.396(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.376(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.365(7) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C11 C11 1.544(7) 3_667 ?
C12 C12 1.542(7) 3_767 ?
C13 C14 1.547(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 Tb1 O10 132.55(9) . 3_667 ?
O4 Tb1 O12 81.36(10) . 3_767 ?
O10 Tb1 O12 73.60(9) 3_667 3_767 ?
O4 Tb1 N1 138.48(10) . . ?
O10 Tb1 N1 81.38(9) 3_667 . ?
O12 Tb1 N1 138.20(10) 3_767 . ?
O4 Tb1 O9 67.48(9) . . ?
O10 Tb1 O9 67.12(9) 3_667 . ?
O12 Tb1 O9 73.84(9) 3_767 . ?
N1 Tb1 O9 125.73(10) . . ?
O4 Tb1 O11 71.55(10) . . ?
O10 Tb1 O11 128.87(9) 3_667 . ?
O12 Tb1 O11 66.59(9) 3_767 . ?
N1 Tb1 O11 108.18(10) . . ?
O9 Tb1 O11 126.07(9) . . ?
O4 Tb1 O5 91.96(10) . . ?
O10 Tb1 O5 86.22(9) 3_667 . ?
O12 Tb1 O5 144.38(9) 3_767 . ?
N1 Tb1 O5 63.28(9) . . ?
O9 Tb1 O5 71.32(9) . . ?
O11 Tb1 O5 143.74(9) . . ?
O4 Tb1 O3 66.73(9) . . ?
O10 Tb1 O3 154.23(9) 3_667 . ?
O12 Tb1 O3 131.35(9) 3_767 . ?
N1 Tb1 O3 74.53(9) . . ?
O9 Tb1 O3 120.87(9) . . ?
O11 Tb1 O3 68.88(9) . . ?
O5 Tb1 O3 74.97(9) . . ?
O4 Tb1 N3 138.50(10) . . ?
O10 Tb1 N3 77.50(9) 3_667 . ?
O12 Tb1 N3 82.53(10) 3_767 . ?
N1 Tb1 N3 59.36(10) . . ?
O9 Tb1 N3 141.61(9) . . ?
O11 Tb1 N3 66.95(9) . . ?
O5 Tb1 N3 121.94(9) . . ?
O3 Tb1 N3 97.47(10) . . ?
O7 Tb2 O6 80.20(9) 4_666 4_666 ?
O7 Tb2 O8 145.99(10) 4_666 1_656 ?
O6 Tb2 O8 79.20(10) 4_666 1_656 ?
O7 Tb2 O15 85.62(10) 4_666 . ?
O6 Tb2 O15 72.15(10) 4_666 . ?
O8 Tb2 O15 113.04(10) 1_656 . ?
O7 Tb2 O1 140.36(10) 4_666 . ?
O6 Tb2 O1 123.20(9) 4_666 . ?
O8 Tb2 O1 73.58(10) 1_656 . ?
O15 Tb2 O1 74.33(10) . . ?
O7 Tb2 O13 102.77(10) 4_666 . ?
O6 Tb2 O13 142.55(10) 4_666 . ?
O8 Tb2 O13 78.60(10) 1_656 . ?
O15 Tb2 O13 144.89(10) . . ?
O1 Tb2 O13 78.06(10) . . ?
O7 Tb2 O2 75.59(9) 4_666 . ?
O6 Tb2 O2 140.79(10) 4_666 . ?
O8 Tb2 O2 135.03(9) 1_656 . ?
O15 Tb2 O2 75.63(10) . . ?
O1 Tb2 O2 66.54(9) . . ?
O13 Tb2 O2 73.72(10) . . ?
O7 Tb2 O14 74.58(10) 4_666 . ?
O6 Tb2 O14 72.26(10) 4_666 . ?
O8 Tb2 O14 73.50(10) 1_656 . ?
O15 Tb2 O14 141.61(10) . . ?
O1 Tb2 O14 139.39(10) . . ?
O13 Tb2 O14 72.71(10) . . ?
O2 Tb2 O14 128.04(10) . . ?
C3 N1 C2 106.8(3) . . ?
C3 N1 Tb1 130.6(2) . . ?
C2 N1 Tb1 122.6(2) . . ?
C3 N2 C1 108.7(3) . . ?
C3 N2 H2 125.7 . . ?
C1 N2 H2 125.7 . . ?
C8 N3 C4 116.9(4) . . ?
C8 N3 Tb1 125.2(3) . . ?
C4 N3 Tb1 116.7(2) . . ?
C13 O1 Tb2 121.2(3) . . ?
C14 O2 Tb2 118.7(2) . . ?
C14 O3 Tb1 113.9(2) . . ?
C13 O4 Tb1 116.0(2) . . ?
C10 O5 Tb1 125.3(2) . . ?
C10 O6 Tb2 147.9(2) . 4_465 ?
C9 O7 Tb2 147.6(2) . 4_465 ?
C9 O8 Tb2 125.0(2) . 1_454 ?
C11 O9 Tb1 118.3(2) . . ?
C11 O10 Tb1 118.7(2) . 3_667 ?
C12 O11 Tb1 117.2(2) . . ?
C12 O12 Tb1 118.0(2) . 3_767 ?
Tb2 O13 H13A 124.9 . . ?
Tb2 O13 H13B 120.7 . . ?
H13A O13 H13B 106.5 . . ?
Tb2 O14 H14A 118.8 . . ?
Tb2 O14 H14B 117.1 . . ?
H14A O14 H14B 107.8 . . ?
Tb2 O15 H15A 111.1 . . ?
Tb2 O15 H15B 118.4 . . ?
H15A O15 H15B 106.8 . . ?
N2 C1 C2 104.8(3) . . ?
N2 C1 C9 119.8(3) . . ?
C2 C1 C9 135.2(3) . . ?
N1 C2 C1 109.5(3) . . ?
N1 C2 C10 114.3(3) . . ?
C1 C2 C10 136.2(3) . . ?
N1 C3 N2 110.2(3) . . ?
N1 C3 C4 119.7(3) . . ?
N2 C3 C4 130.1(3) . . ?
N3 C4 C5 123.3(4) . . ?
N3 C4 C3 112.4(3) . . ?
C5 C4 C3 124.3(4) . . ?
C4 C5 C6 117.7(4) . . ?
C4 C5 H5 121.1 . . ?
C6 C5 H5 121.1 . . ?
C7 C6 C5 118.8(4) . . ?
C7 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
C8 C7 C6 119.4(4) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
N3 C8 C7 123.8(4) . . ?
N3 C8 H8 118.1 . . ?
C7 C8 H8 118.1 . . ?
O7 C9 O8 125.1(3) . . ?
O7 C9 C1 119.9(3) . . ?
O8 C9 C1 115.0(3) . . ?
O6 C10 O5 123.4(3) . . ?
O6 C10 C2 123.2(3) . . ?
O5 C10 C2 113.4(3) . . ?
O9 C11 O10 126.1(3) . . ?
O9 C11 C11 117.1(4) . 3_667 ?
O10 C11 C11 116.8(4) . 3_667 ?
O11 C12 O12 126.3(4) . . ?
O11 C12 C12 117.3(4) . 3_767 ?
O12 C12 C12 116.4(4) . 3_767 ?
O1 C13 O4 126.5(4) . . ?
O1 C13 C14 117.2(3) . . ?
O4 C13 C14 116.3(3) . . ?
O3 C14 O2 127.3(4) . . ?
O3 C14 C13 117.2(3) . . ?
O2 C14 C13 115.5(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N2 C1 C2 0.3(4) . . . . ?
C3 N2 C1 C9 -176.5(3) . . . . ?
C3 N1 C2 C1 -0.3(4) . . . . ?
Tb1 N1 C2 C1 -177.5(2) . . . . ?
C3 N1 C2 C10 -179.1(3) . . . . ?
Tb1 N1 C2 C10 3.7(4) . . . . ?
N2 C1 C2 N1 0.0(4) . . . . ?
C9 C1 C2 N1 176.0(4) . . . . ?
N2 C1 C2 C10 178.4(4) . . . . ?
C9 C1 C2 C10 -5.6(8) . . . . ?
C2 N1 C3 N2 0.5(4) . . . . ?
Tb1 N1 C3 N2 177.4(2) . . . . ?
C2 N1 C3 C4 -179.8(3) . . . . ?
Tb1 N1 C3 C4 -2.9(5) . . . . ?
C1 N2 C3 N1 -0.5(4) . . . . ?
C1 N2 C3 C4 179.8(4) . . . . ?
C8 N3 C4 C5 2.1(6) . . . . ?
Tb1 N3 C4 C5 -166.4(3) . . . . ?
C8 N3 C4 C3 -179.6(4) . . . . ?
Tb1 N3 C4 C3 11.9(4) . . . . ?
N1 C3 C4 N3 -7.2(5) . . . . ?
N2 C3 C4 N3 172.4(4) . . . . ?
N1 C3 C4 C5 171.1(4) . . . . ?
N2 C3 C4 C5 -9.3(7) . . . . ?
N3 C4 C5 C6 -2.5(7) . . . . ?
C3 C4 C5 C6 179.3(4) . . . . ?
C4 C5 C6 C7 0.5(7) . . . . ?
C5 C6 C7 C8 1.8(8) . . . . ?
C4 N3 C8 C7 0.4(7) . . . . ?
Tb1 N3 C8 C7 167.9(4) . . . . ?
C6 C7 C8 N3 -2.4(8) . . . . ?
Tb2 O7 C9 O8 135.1(4) 4_465 . . . ?
Tb2 O7 C9 C1 -44.0(6) 4_465 . . . ?
Tb2 O8 C9 O7 -6.1(5) 1_454 . . . ?
Tb2 O8 C9 C1 173.0(2) 1_454 . . . ?
N2 C1 C9 O7 -172.7(3) . . . . ?
C2 C1 C9 O7 11.7(7) . . . . ?
N2 C1 C9 O8 8.1(5) . . . . ?
C2 C1 C9 O8 -167.4(4) . . . . ?
Tb2 O6 C10 O5 -170.0(3) 4_465 . . . ?
Tb2 O6 C10 C2 10.8(7) 4_465 . . . ?
Tb1 O5 C10 O6 169.0(3) . . . . ?
Tb1 O5 C10 C2 -11.8(4) . . . . ?
N1 C2 C10 O6 -175.9(3) . . . . ?
C1 C2 C10 O6 5.7(7) . . . . ?
N1 C2 C10 O5 4.8(5) . . . . ?
C1 C2 C10 O5 -173.5(4) . . . . ?
Tb1 O9 C11 O10 -168.8(3) . . . . ?
Tb1 O9 C11 C11 10.1(5) . . . 3_667 ?
Tb1 O10 C11 O9 -169.4(3) 3_667 . . . ?
Tb1 O10 C11 C11 11.7(5) 3_667 . . 3_667 ?
Tb1 O11 C12 O12 163.2(3) . . . . ?
Tb1 O11 C12 C12 -14.9(5) . . . 3_767 ?
Tb1 O12 C12 O11 164.1(3) 3_767 . . . ?
Tb1 O12 C12 C12 -17.8(5) 3_767 . . 3_767 ?
Tb2 O1 C13 O4 -179.4(3) . . . . ?
Tb2 O1 C13 C14 -1.3(5) . . . . ?
Tb1 O4 C13 O1 148.3(3) . . . . ?
Tb1 O4 C13 C14 -29.7(4) . . . . ?
Tb1 O3 C14 O2 -161.8(3) . . . . ?
Tb1 O3 C14 C13 17.2(4) . . . . ?
Tb2 O2 C14 O3 168.0(3) . . . . ?
Tb2 O2 C14 C13 -11.0(4) . . . . ?
O1 C13 C14 O3 -170.7(4) . . . . ?
O4 C13 C14 O3 7.5(5) . . . . ?
O1 C13 C14 O2 8.4(5) . . . . ?
O4 C13 C14 O2 -173.4(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
O15 H15B O2 0.82 1.93 2.743(4) 167.7 4_566
O15 H15A O17 0.82 2.00 2.775(6) 156.5 1_556
O14 H14B O5 0.82 1.97 2.766(4) 164.4 1_655
O14 H14A O16 0.82 2.11 2.918(7) 173.4 4_666
O13 H13B O5 0.82 2.06 2.833(4) 156.5 1_655
O13 H13A O12 0.82 2.01 2.829(4) 173.3 .
N2 H2 O10 0.86 2.20 2.956(4) 146.3 1_554
N2 H2 O8 0.86 2.50 2.707(4) 94.3 .

_refine_diff_density_max         1.016
_refine_diff_density_min         -0.612
_refine_diff_density_rms         0.113

####################################################################### 
# 
# 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_Z9-Dy-zb26-14R1
_database_code_depnum_ccdc_archive 'CCDC 1506105'
_audit_update_record             
;
2017-02-28 deposited with the CCDC.
2017-03-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H15 Dy2 N3 O17'
_chemical_formula_weight         822.29

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Dy Dy -0.1290 4.5270 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   9.4280(19)
_cell_length_b                   22.415(5)
_cell_length_c                   10.051(2)
_cell_angle_alpha                90
_cell_angle_beta                 102.12(3)
_cell_angle_gamma                90
_cell_volume                     2076.7(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    11485
_cell_measurement_theta_min      2.10
_cell_measurement_theta_max      30.95

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.630
_exptl_crystal_F_000             1552
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    7.455
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.720
_diffrn_radiation_type           synchrotron
_diffrn_source                   'synchrotron, 3W1A at BSRF'
_diffrn_measurement_device_type  mar165
_diffrn_measurement_method       'oscillation mode'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7251
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.238
_diffrn_reflns_theta_max         25.986
_diffrn_reflns_theta_full        25.595
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3924
_reflns_number_gt                3688
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0257P)²+4.6806P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3924
_refine_ls_number_parameters     326
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0248
_refine_ls_R_factor_gt           0.0230
_refine_ls_wR_factor_ref         0.0525
_refine_ls_wR_factor_gt          0.0516
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Dy1 Dy 1.25050(2) 0.27717(2) 1.04663(2) 0.00555(6) Uani 1 1 d . . . . .
Dy2 Dy 0.71833(2) 0.43461(2) 0.85831(2) 0.00348(6) Uani 1 1 d . . . . .
N1 N 0.5983(3) 0.41520(13) 0.6254(3) 0.0052(5) Uani 1 1 d . . . . .
N2 N 0.5341(3) 0.41369(13) 0.4025(3) 0.0058(5) Uani 1 1 d . . . . .
H2 H 0.524060 0.426680 0.321414 0.007 Uiso 1 1 d R U . . .
N3 N 0.7766(3) 0.50743(15) 0.6483(3) 0.0103(6) Uani 1 1 d . . . . .
O1 O 1.0677(3) 0.33781(12) 1.1094(2) 0.0113(5) Uani 1 1 d . . . . .
O2 O 1.0343(3) 0.28800(12) 0.8635(2) 0.0107(5) Uani 1 1 d . . . . .
O3 O 0.8303(3) 0.34248(11) 0.7913(2) 0.0099(5) Uani 1 1 d . . . . .
O4 O 0.8490(3) 0.38065(12) 1.0488(2) 0.0107(5) Uani 1 1 d . . . . .
O5 O 0.5242(3) 0.35985(11) 0.8231(2) 0.0072(5) Uani 1 1 d . . . . .
O6 O 0.3776(3) 0.29458(12) 0.6937(2) 0.0091(5) Uani 1 1 d . . . . .
O7 O 0.2771(3) 0.29313(12) 0.3914(2) 0.0082(5) Uani 1 1 d . . . . .
O8 O 0.3651(3) 0.33741(12) 0.2273(2) 0.0089(5) Uani 1 1 d . . . . .
O9 O 0.6013(3) 0.43610(11) 1.0509(2) 0.0087(5) Uani 1 1 d . . . . .
O10 O 0.4695(2) 0.49149(11) 1.1657(2) 0.0075(5) Uani 1 1 d . . . . .
O11 O 0.9769(3) 0.44787(12) 0.8687(2) 0.0090(5) Uani 1 1 d . . . . .
O12 O 1.1808(3) 0.48171(11) 1.0047(2) 0.0102(5) Uani 1 1 d . . . . .
O13 O 1.2777(3) 0.36961(12) 0.9344(2) 0.0107(5) Uani 1 1 d . . . . .
H13A H 1.247955 0.401929 0.955277 0.016 Uiso 1 1 d R U . . .
H13B H 1.354197 0.375529 0.909939 0.016 Uiso 1 1 d R U . . .
O14 O 1.5097(3) 0.28360(12) 1.0332(3) 0.0125(5) Uani 1 1 d . . . . .
H14A H 1.552039 0.300005 1.103263 0.019 Uiso 1 1 d R U . . .
H14B H 1.513403 0.306170 0.969814 0.019 Uiso 1 1 d R U . . .
O15 O 1.0771(3) 0.21059(12) 1.1046(3) 0.0124(5) Uani 1 1 d . . . . .
H15A H 0.995730 0.216975 1.058843 0.019 Uiso 1 1 d R U . . .
H15B H 1.070008 0.208959 1.184417 0.019 Uiso 1 1 d R U . . .
O16 O 0.7154(4) 0.1740(2) 0.7488(4) 0.0472(11) Uani 1 1 d . . . . .
H16A H 0.781371 0.159844 0.716578 0.071 Uiso 1 1 d R U . . .
H16B H 0.738739 0.169817 0.831586 0.071 Uiso 1 1 d R U . . .
O17 O 0.7742(3) 0.20923(15) 0.0277(3) 0.0234(6) Uani 1 1 d . . . . .
H17A H 0.729103 0.240565 0.012546 0.035 Uiso 1 1 d R U . . .
H17B H 0.808992 0.208240 0.109685 0.035 Uiso 1 1 d R U . . .
C1 C 0.4560(3) 0.36928(15) 0.4488(3) 0.0054(6) Uani 1 1 d . . . . .
C2 C 0.4980(3) 0.37080(15) 0.5894(3) 0.0053(6) Uani 1 1 d . . . . .
C3 C 0.6193(4) 0.44017(15) 0.5117(3) 0.0048(6) Uani 1 1 d . . . . .
C4 C 0.7235(4) 0.48952(16) 0.5185(3) 0.0071(6) Uani 1 1 d . . . . .
C5 C 0.7649(4) 0.51421(18) 0.4051(4) 0.0127(7) Uani 1 1 d . . . . .
H5 H 0.727567 0.499352 0.316077 0.015 Uiso 1 1 calc R U . . .
C6 C 0.8633(4) 0.56168(18) 0.4272(4) 0.0170(8) Uani 1 1 d . . . . .
H6 H 0.894644 0.579943 0.353093 0.020 Uiso 1 1 calc R U . . .
C7 C 0.9144(4) 0.58159(18) 0.5588(4) 0.0184(8) Uani 1 1 d . . . . .
H7 H 0.979648 0.614355 0.576031 0.022 Uiso 1 1 calc R U . . .
C8 C 0.8693(4) 0.55318(17) 0.6654(4) 0.0134(7) Uani 1 1 d . . . . .
H8 H 0.906470 0.567005 0.755311 0.016 Uiso 1 1 calc R U . . .
C9 C 0.3578(3) 0.33023(15) 0.3497(3) 0.0057(6) Uani 1 1 d . U . . .
C10 C 0.4617(3) 0.33826(15) 0.7068(3) 0.0052(6) Uani 1 1 d . . . . .
C11 C 0.5209(3) 0.47858(15) 1.0620(3) 0.0057(6) Uani 1 1 d . . . . .
C12 C 1.0452(4) 0.47976(15) 0.9625(3) 0.0067(7) Uani 1 1 d . . . . .
C13 C 0.9530(4) 0.34932(16) 1.0263(3) 0.0085(7) Uani 1 1 d . . . . .
C14 C 0.9368(4) 0.32420(16) 0.8801(3) 0.0093(7) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Dy1 O7 2.268(2) 4_666 ?
Dy1 O6 2.338(2) 4_666 ?
Dy1 O8 2.338(2) 1_656 ?
Dy1 O15 2.375(3) . ?
Dy1 O1 2.382(3) . ?
Dy1 O13 2.399(3) . ?
Dy1 O2 2.455(3) . ?
Dy1 O14 2.480(3) . ?
Dy2 O4 2.378(2) . ?
Dy2 O10 2.400(2) 3_667 ?
Dy2 O12 2.401(2) 3_767 ?
Dy2 N1 2.416(3) . ?
Dy2 O9 2.421(3) . ?
Dy2 O11 2.437(2) . ?
Dy2 O5 2.452(2) . ?
Dy2 O3 2.476(3) . ?
Dy2 N3 2.812(3) . ?
N1 C3 1.324(4) . ?
N1 C2 1.368(4) . ?
N2 C3 1.354(4) . ?
N2 C1 1.376(4) . ?
N2 H2 0.8515 . ?
N3 C8 1.335(5) . ?
N3 C4 1.356(4) . ?
O1 C13 1.247(4) . ?
O2 C14 1.263(4) . ?
O3 C14 1.264(4) . ?
O4 C13 1.264(4) . ?
O5 C10 1.288(4) . ?
O6 C10 1.249(4) . ?
O7 C9 1.257(4) . ?
O8 C9 1.257(4) . ?
O9 C11 1.237(4) . ?
O10 C11 1.272(4) . ?
O11 C12 1.249(4) . ?
O12 C12 1.260(4) . ?
O13 H13A 0.8200 . ?
O13 H13B 0.8199 . ?
O14 H14A 0.8201 . ?
O14 H14B 0.8200 . ?
O15 H15A 0.8201 . ?
O15 H15B 0.8201 . ?
O16 H16A 0.8226 . ?
O16 H16B 0.8201 . ?
O17 H17A 0.8183 . ?
O17 H17B 0.8211 . ?
C1 C2 1.386(4) . ?
C1 C9 1.493(4) . ?
C2 C10 1.487(5) . ?
C3 C4 1.471(5) . ?
C4 C5 1.395(5) . ?
C5 C6 1.399(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.383(6) . ?
C6 H6 0.9500 . ?
C7 C8 1.387(6) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C11 C11 1.558(6) 3_667 ?
C12 C12 1.546(7) 3_767 ?
C13 C14 1.552(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O7 Dy1 O6 80.84(9) 4_666 4_666 ?
O7 Dy1 O8 146.70(9) 4_666 1_656 ?
O6 Dy1 O8 79.29(9) 4_666 1_656 ?
O7 Dy1 O15 85.02(9) 4_666 . ?
O6 Dy1 O15 72.57(9) 4_666 . ?
O8 Dy1 O15 113.73(9) 1_656 . ?
O7 Dy1 O1 140.30(9) 4_666 . ?
O6 Dy1 O1 121.91(9) 4_666 . ?
O8 Dy1 O1 72.95(9) 1_656 . ?
O15 Dy1 O1 73.74(10) . . ?
O7 Dy1 O13 103.80(9) 4_666 . ?
O6 Dy1 O13 143.17(9) 4_666 . ?
O8 Dy1 O13 77.80(9) 1_656 . ?
O15 Dy1 O13 143.66(9) . . ?
O1 Dy1 O13 77.68(9) . . ?
O7 Dy1 O2 75.35(9) 4_666 . ?
O6 Dy1 O2 140.98(9) 4_666 . ?
O8 Dy1 O2 134.51(9) 1_656 . ?
O15 Dy1 O2 74.94(9) . . ?
O1 Dy1 O2 67.00(8) . . ?
O13 Dy1 O2 73.49(9) . . ?
O7 Dy1 O14 75.54(9) 4_666 . ?
O6 Dy1 O14 72.19(9) 4_666 . ?
O8 Dy1 O14 73.06(9) 1_656 . ?
O15 Dy1 O14 141.89(9) . . ?
O1 Dy1 O14 139.25(9) . . ?
O13 Dy1 O14 73.75(9) . . ?
O2 Dy1 O14 128.75(9) . . ?
O4 Dy2 O10 132.74(8) . 3_667 ?
O4 Dy2 O12 81.95(9) . 3_767 ?
O10 Dy2 O12 73.36(8) 3_667 3_767 ?
O4 Dy2 N1 138.28(9) . . ?
O10 Dy2 N1 80.86(9) 3_667 . ?
O12 Dy2 N1 138.13(9) 3_767 . ?
O4 Dy2 O9 67.01(8) . . ?
O10 Dy2 O9 67.69(8) 3_667 . ?
O12 Dy2 O9 73.91(9) 3_767 . ?
N1 Dy2 O9 125.29(9) . . ?
O4 Dy2 O11 71.52(9) . . ?
O10 Dy2 O11 129.11(9) 3_667 . ?
O12 Dy2 O11 66.93(8) 3_767 . ?
N1 Dy2 O11 108.93(9) . . ?
O9 Dy2 O11 125.73(8) . . ?
O4 Dy2 O5 90.76(9) . . ?
O10 Dy2 O5 86.81(9) 3_667 . ?
O12 Dy2 O5 144.10(8) 3_767 . ?
N1 Dy2 O5 63.48(9) . . ?
O9 Dy2 O5 70.91(8) . . ?
O11 Dy2 O5 143.08(9) . . ?
O4 Dy2 O3 67.44(8) . . ?
O10 Dy2 O3 153.64(8) 3_667 . ?
O12 Dy2 O3 131.85(8) 3_767 . ?
N1 Dy2 O3 74.10(9) . . ?
O9 Dy2 O3 121.39(8) . . ?
O11 Dy2 O3 68.49(8) . . ?
O5 Dy2 O3 74.86(8) . . ?
O4 Dy2 N3 138.56(8) . . ?
O10 Dy2 N3 77.30(9) 3_667 . ?
O12 Dy2 N3 82.00(9) 3_767 . ?
N1 Dy2 N3 60.19(9) . . ?
O9 Dy2 N3 141.78(9) . . ?
O11 Dy2 N3 67.05(9) . . ?
O5 Dy2 N3 123.09(8) . . ?
O3 Dy2 N3 96.79(9) . . ?
C3 N1 C2 107.5(3) . . ?
C3 N1 Dy2 129.4(2) . . ?
C2 N1 Dy2 123.0(2) . . ?
C3 N2 C1 108.1(3) . . ?
C3 N2 H2 123.6 . . ?
C1 N2 H2 127.7 . . ?
C8 N3 C4 116.8(3) . . ?
C8 N3 Dy2 125.1(2) . . ?
C4 N3 Dy2 117.4(2) . . ?
C13 O1 Dy1 121.0(2) . . ?
C14 O2 Dy1 118.5(2) . . ?
C14 O3 Dy2 113.5(2) . . ?
C13 O4 Dy2 115.4(2) . . ?
C10 O5 Dy2 124.9(2) . . ?
C10 O6 Dy1 146.7(2) . 4_465 ?
C9 O7 Dy1 148.3(2) . 4_465 ?
C9 O8 Dy1 125.1(2) . 1_454 ?
C11 O9 Dy2 118.3(2) . . ?
C11 O10 Dy2 118.3(2) . 3_667 ?
C12 O11 Dy2 117.1(2) . . ?
C12 O12 Dy2 118.1(2) . 3_767 ?
Dy1 O13 H13A 124.5 . . ?
Dy1 O13 H13B 117.9 . . ?
H13A O13 H13B 107.7 . . ?
Dy1 O14 H14A 106.7 . . ?
Dy1 O14 H14B 106.3 . . ?
H14A O14 H14B 107.3 . . ?
Dy1 O15 H15A 111.4 . . ?
Dy1 O15 H15B 118.0 . . ?
H15A O15 H15B 107.3 . . ?
H16A O16 H16B 107.0 . . ?
H17A O17 H17B 107.0 . . ?
N2 C1 C2 105.6(3) . . ?
N2 C1 C9 120.0(3) . . ?
C2 C1 C9 134.4(3) . . ?
N1 C2 C1 108.7(3) . . ?
N1 C2 C10 114.1(3) . . ?
C1 C2 C10 137.2(3) . . ?
N1 C3 N2 110.1(3) . . ?
N1 C3 C4 119.8(3) . . ?
N2 C3 C4 130.1(3) . . ?
N3 C4 C5 124.0(3) . . ?
N3 C4 C3 112.0(3) . . ?
C5 C4 C3 124.0(3) . . ?
C4 C5 C6 117.5(3) . . ?
C4 C5 H5 121.3 . . ?
C6 C5 H5 121.3 . . ?
C7 C6 C5 119.0(4) . . ?
C7 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C6 C7 C8 119.2(4) . . ?
C6 C7 H7 120.4 . . ?
C8 C7 H7 120.4 . . ?
N3 C8 C7 123.5(3) . . ?
N3 C8 H8 118.2 . . ?
C7 C8 H8 118.2 . . ?
O8 C9 O7 124.9(3) . . ?
O8 C9 C1 115.1(3) . . ?
O7 C9 C1 120.0(3) . . ?
O6 C10 O5 123.3(3) . . ?
O6 C10 C2 123.2(3) . . ?
O5 C10 C2 113.5(3) . . ?
O9 C11 O10 126.6(3) . . ?
O9 C11 C11 117.3(4) . 3_667 ?
O10 C11 C11 116.1(4) . 3_667 ?
O11 C12 O12 126.9(3) . . ?
O11 C12 C12 117.0(4) . 3_767 ?
O12 C12 C12 116.1(4) . 3_767 ?
O1 C13 O4 126.3(3) . . ?
O1 C13 C14 117.3(3) . . ?
O4 C13 C14 116.4(3) . . ?
O2 C14 O3 127.4(3) . . ?
O2 C14 C13 115.4(3) . . ?
O3 C14 C13 117.2(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N2 C1 C2 0.2(4) . . . . ?
C3 N2 C1 C9 -176.9(3) . . . . ?
C3 N1 C2 C1 -0.6(4) . . . . ?
Dy2 N1 C2 C1 -176.7(2) . . . . ?
C3 N1 C2 C10 -179.8(3) . . . . ?
Dy2 N1 C2 C10 4.1(4) . . . . ?
N2 C1 C2 N1 0.2(4) . . . . ?
C9 C1 C2 N1 176.7(4) . . . . ?
N2 C1 C2 C10 179.1(4) . . . . ?
C9 C1 C2 C10 -4.4(7) . . . . ?
C2 N1 C3 N2 0.7(4) . . . . ?
Dy2 N1 C3 N2 176.6(2) . . . . ?
C2 N1 C3 C4 -179.5(3) . . . . ?
Dy2 N1 C3 C4 -3.7(5) . . . . ?
C1 N2 C3 N1 -0.6(4) . . . . ?
C1 N2 C3 C4 179.7(3) . . . . ?
C8 N3 C4 C5 2.8(5) . . . . ?
Dy2 N3 C4 C5 -167.6(3) . . . . ?
C8 N3 C4 C3 -178.3(3) . . . . ?
Dy2 N3 C4 C3 11.3(3) . . . . ?
N1 C3 C4 N3 -6.2(4) . . . . ?
N2 C3 C4 N3 173.5(3) . . . . ?
N1 C3 C4 C5 172.7(3) . . . . ?
N2 C3 C4 C5 -7.6(6) . . . . ?
N3 C4 C5 C6 -2.3(5) . . . . ?
C3 C4 C5 C6 179.0(3) . . . . ?
C4 C5 C6 C7 0.0(6) . . . . ?
C5 C6 C7 C8 1.4(6) . . . . ?
C4 N3 C8 C7 -1.2(5) . . . . ?
Dy2 N3 C8 C7 168.4(3) . . . . ?
C6 C7 C8 N3 -0.9(6) . . . . ?
Dy1 O8 C9 O7 -7.0(5) 1_454 . . . ?
Dy1 O8 C9 C1 172.1(2) 1_454 . . . ?
Dy1 O7 C9 O8 136.4(3) 4_465 . . . ?
Dy1 O7 C9 C1 -42.8(6) 4_465 . . . ?
N2 C1 C9 O8 6.9(5) . . . . ?
C2 C1 C9 O8 -169.2(4) . . . . ?
N2 C1 C9 O7 -173.8(3) . . . . ?
C2 C1 C9 O7 10.1(6) . . . . ?
Dy1 O6 C10 O5 -168.4(3) 4_465 . . . ?
Dy1 O6 C10 C2 12.3(6) 4_465 . . . ?
Dy2 O5 C10 O6 169.8(2) . . . . ?
Dy2 O5 C10 C2 -10.8(4) . . . . ?
N1 C2 C10 O6 -176.6(3) . . . . ?
C1 C2 C10 O6 4.5(6) . . . . ?
N1 C2 C10 O5 4.1(4) . . . . ?
C1 C2 C10 O5 -174.8(4) . . . . ?
Dy2 O9 C11 O10 -168.1(3) . . . . ?
Dy2 O9 C11 C11 11.0(5) . . . 3_667 ?
Dy2 O10 C11 O9 -168.6(3) 3_667 . . . ?
Dy2 O10 C11 C11 12.2(4) 3_667 . . 3_667 ?
Dy2 O11 C12 O12 162.9(3) . . . . ?
Dy2 O11 C12 C12 -15.7(5) . . . 3_767 ?
Dy2 O12 C12 O11 163.4(3) 3_767 . . . ?
Dy2 O12 C12 C12 -18.0(5) 3_767 . . 3_767 ?
Dy1 O1 C13 O4 179.7(3) . . . . ?
Dy1 O1 C13 C14 -1.8(4) . . . . ?
Dy2 O4 C13 O1 148.5(3) . . . . ?
Dy2 O4 C13 C14 -30.0(4) . . . . ?
Dy1 O2 C14 O3 168.3(3) . . . . ?
Dy1 O2 C14 C13 -10.7(4) . . . . ?
Dy2 O3 C14 O2 -162.0(3) . . . . ?
Dy2 O3 C14 C13 16.9(4) . . . . ?
O1 C13 C14 O2 8.5(5) . . . . ?
O4 C13 C14 O2 -172.8(3) . . . . ?
O1 C13 C14 O3 -170.6(3) . . . . ?
O4 C13 C14 O3 8.1(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
O17 H17B O3 0.82 2.12 2.838(4) 145.4 4_565
O17 H17A O14 0.82 2.33 3.009(4) 140.8 1_454
O16 H16B O17 0.82 2.12 2.852(5) 148.4 1_556
O16 H16A O4 0.82 2.13 2.862(4) 148.6 4_565
O15 H15B O2 0.82 1.90 2.716(4) 172.9 4_566
O15 H15A O17 0.82 2.05 2.798(4) 150.8 1_556
O14 H14B O5 0.82 1.92 2.742(4) 179.1 1_655
O14 H14A O16 0.82 1.98 2.756(5) 158.6 4_666
O13 H13B O5 0.82 2.01 2.791(4) 158.9 1_655
O13 H13A O12 0.82 1.99 2.814(4) 178.3 .
N2 H2 O10 0.85 2.12 2.910(4) 154.5 1_554

_refine_diff_density_max         1.722
_refine_diff_density_min         -1.529
_refine_diff_density_rms         0.180

####################################################################### 
# 
# 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_Z6-Eu-zb60-14R1
_database_code_depnum_ccdc_archive 'CCDC 1506102'
_audit_update_record             
;
2017-02-28 deposited with the CCDC.
2017-03-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H15 Eu2 N3 O17'
_chemical_formula_weight         801.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Eu Eu -0.0970 3.7690 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   9.5740(19)
_cell_length_b                   22.547(5)
_cell_length_c                   10.122(2)
_cell_angle_alpha                90
_cell_angle_beta                 102.04(3)
_cell_angle_gamma                90
_cell_volume                     2136.9(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    11418
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      30.95

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.490
_exptl_crystal_F_000             1528
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    6.068
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3684
_exptl_absorpt_correction_T_max  0.4694
_exptl_absorpt_process_details   '(HKL SCALEPACK; Otwinowski & Minor, 1997)'

_exptl_special_details           ?

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.720
_diffrn_radiation_type           synchrotron
_diffrn_source                   'synchrotron, 3W1A at BSRF'
_diffrn_measurement_device_type  mar165
_diffrn_measurement_method       'oscillation mode'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8221
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.203
_diffrn_reflns_theta_max         26.997
_diffrn_reflns_theta_full        25.595
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4489
_reflns_number_gt                4050
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0491P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4489
_refine_ls_number_parameters     338
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0293
_refine_ls_wR_factor_ref         0.0754
_refine_ls_wR_factor_gt          0.0736
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Eu1 Eu -0.25085(2) 0.72216(2) -0.04316(2) 0.00447(8) Uani 1 1 d . . . . .
Eu2 Eu 0.28188(2) 0.56499(2) 0.14376(2) 0.00388(8) Uani 1 1 d . . . . .
N1 N 0.2272(4) 0.49221(17) 0.3582(4) 0.0135(8) Uani 1 1 d . U . . .
N2 N 0.4018(4) 0.58492(14) 0.3786(3) 0.0059(7) Uani 1 1 d . . . . .
N3 N 0.4654(4) 0.58658(14) 0.6003(3) 0.0057(7) Uani 1 1 d . . . . .
H3 H 0.475544 0.571614 0.679749 0.007 Uiso 1 1 d R U . . .
O1 O -0.0675(3) 0.66083(13) -0.1055(3) 0.0105(6) Uani 1 1 d . . . . .
O2 O -0.0347(3) 0.71058(13) 0.1391(3) 0.0085(6) Uani 1 1 d . . . . .
O3 O 0.1679(3) 0.65797(12) 0.2095(3) 0.0077(6) Uani 1 1 d . . . . .
O4 O 0.1511(3) 0.62078(13) -0.0473(3) 0.0099(6) Uani 1 1 d . . . . .
O5 O -0.0743(3) 0.78886(13) -0.1010(3) 0.0105(6) Uani 1 1 d . . . . .
H5A H -0.067523 0.786018 -0.180180 0.016 Uiso 1 1 d R U . . .
H5B H 0.006792 0.786852 -0.054664 0.016 Uiso 1 1 d R U . . .
O6 O -0.5112(3) 0.71532(13) -0.0290(3) 0.0105(6) Uani 1 1 d . . . . .
H6A H -0.566507 0.699951 -0.092581 0.016 Uiso 1 1 d R U . . .
H6B H -0.531443 0.702508 0.040502 0.016 Uiso 1 1 d R U . . .
O7 O -0.2781(3) 0.62825(12) 0.0707(3) 0.0099(6) Uani 1 1 d . . . . .
H7A H -0.240446 0.597685 0.051416 0.015 Uiso 1 1 d R U . . .
H7B H -0.353332 0.618945 0.091758 0.015 Uiso 1 1 d R U . . .
O8 O 0.3995(3) 0.56390(12) -0.0488(3) 0.0083(6) Uani 1 1 d . . . . .
O9 O 0.5299(3) 0.50961(12) -0.1646(3) 0.0082(6) Uani 1 1 d . . . . .
O10 O 0.1783(3) 0.48098(12) 0.0037(3) 0.0106(6) Uani 1 1 d . . . . .
O11 O -0.0243(3) 0.44898(13) -0.1326(3) 0.0084(6) Uani 1 1 d . . . . .
O12 O 0.4782(3) 0.63990(12) 0.1819(3) 0.0066(6) Uani 1 1 d . . . . .
O13 O 0.6238(3) 0.70400(13) 0.3117(3) 0.0081(6) Uani 1 1 d . . . . .
O14 O 0.7205(3) 0.70621(13) 0.6139(3) 0.0084(6) Uani 1 1 d . . . . .
O15 O 0.6329(3) 0.66118(13) 0.7754(3) 0.0086(6) Uani 1 1 d . . . . .
O16 O 0.7130(4) 0.3255(2) 0.2453(4) 0.0412(12) Uani 1 1 d D . . . .
H16A H 0.772(6) 0.342(3) 0.209(6) 0.062 Uiso 1 1 d D U . . .
H16B H 0.748(7) 0.324(3) 0.3266(17) 0.062 Uiso 1 1 d D U . . .
O17 O 0.7741(4) 0.20911(16) 0.0258(3) 0.0191(7) Uani 1 1 d D . . . .
H17A H 0.798(5) 0.194(2) 0.101(3) 0.029 Uiso 1 1 d D U . . .
H17B H 0.701(4) 0.228(2) 0.025(5) 0.029 Uiso 1 1 d D U . . .
C1 C 0.0478(4) 0.65027(17) -0.0250(4) 0.0073(8) Uani 1 1 d . U . . .
C2 C 0.0627(4) 0.67565(17) 0.1220(4) 0.0077(8) Uani 1 1 d . . . . .
C3 C 0.0438(4) 0.47986(16) -0.0382(4) 0.0053(8) Uani 1 1 d . . . . .
C4 C 0.4786(4) 0.52144(16) -0.0613(4) 0.0056(8) Uani 1 1 d . U . . .
C5 C 0.5395(4) 0.66089(18) 0.2976(4) 0.0061(8) Uani 1 1 d . . . . .
C6 C 0.6408(4) 0.66910(17) 0.6541(4) 0.0065(8) Uani 1 1 d . . . . .
C7 C 0.5023(4) 0.62899(16) 0.4142(4) 0.0041(7) Uani 1 1 d . . . . .
C8 C 0.5440(4) 0.63103(17) 0.5542(4) 0.0050(7) Uani 1 1 d . . . . .
C9 C 0.3822(4) 0.56007(17) 0.4925(4) 0.0052(8) Uani 1 1 d . . . . .
C10 C 0.2785(4) 0.51114(18) 0.4873(4) 0.0082(8) Uani 1 1 d . . . . .
C11 C 0.2373(5) 0.4871(2) 0.5995(5) 0.0165(10) Uani 1 1 d . . . . .
H11 H 0.273147 0.502141 0.687718 0.020 Uiso 1 1 calc R U . . .
C12 C 0.1403(6) 0.4395(2) 0.5772(6) 0.0247(12) Uani 1 1 d . . . . .
H12 H 0.108107 0.421606 0.650416 0.030 Uiso 1 1 calc R U . . .
C13 C 0.0921(5) 0.4190(2) 0.4454(6) 0.0257(12) Uani 1 1 d . . . . .
H13 H 0.029833 0.385764 0.428609 0.031 Uiso 1 1 calc R U . . .
C14 C 0.1346(5) 0.4468(2) 0.3409(5) 0.0174(10) Uani 1 1 d . . . . .
H14 H 0.097004 0.433362 0.251544 0.021 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Eu1 O14 2.322(3) 4_475 ?
Eu1 O13 2.374(3) 4_475 ?
Eu1 O15 2.377(3) 1_454 ?
Eu1 O1 2.419(3) . ?
Eu1 O5 2.424(3) . ?
Eu1 O7 2.450(3) . ?
Eu1 O2 2.482(3) . ?
Eu1 O6 2.531(3) . ?
Eu1 C6 3.251(4) 1_454 ?
Eu1 C1 3.259(4) . ?
Eu2 O4 2.425(3) . ?
Eu2 O9 2.442(3) 3_665 ?
Eu2 O8 2.446(3) . ?
Eu2 O10 2.449(3) . ?
Eu2 N2 2.456(3) . ?
Eu2 O11 2.465(3) 3_565 ?
Eu2 O12 2.496(3) . ?
Eu2 O3 2.516(3) . ?
Eu2 N1 2.855(4) . ?
Eu2 C1 3.169(4) . ?
Eu2 C4 3.233(4) . ?
Eu2 C2 3.238(4) . ?
N1 C14 1.342(6) . ?
N1 C10 1.365(5) . ?
N2 C9 1.330(5) . ?
N2 C7 1.378(5) . ?
N3 C9 1.349(5) . ?
N3 C8 1.391(5) . ?
N3 H3 0.8591 . ?
O1 C1 1.251(5) . ?
O2 C2 1.259(5) . ?
O3 C2 1.260(5) . ?
O4 C1 1.250(5) . ?
O5 H5A 0.8200 . ?
O5 H5B 0.8200 . ?
O6 H6A 0.8202 . ?
O6 H6B 0.8201 . ?
O7 H7A 0.8199 . ?
O7 H7B 0.8200 . ?
O8 C4 1.244(5) . ?
O9 C4 1.273(5) . ?
O10 C3 1.269(5) . ?
O11 C3 1.250(5) . ?
O12 C5 1.286(5) . ?
O13 C5 1.252(5) . ?
O14 C6 1.256(5) . ?
O15 C6 1.258(5) . ?
O16 H16A 0.820(10) . ?
O16 H16B 0.821(10) . ?
O17 H17A 0.822(10) . ?
O17 H17B 0.821(10) . ?
C1 C2 1.572(6) . ?
C3 C3 1.549(8) 3_565 ?
C4 C4 1.559(7) 3_665 ?
C5 C7 1.487(5) . ?
C6 C8 1.492(5) . ?
C7 C8 1.391(5) . ?
C9 C10 1.478(5) . ?
C10 C11 1.388(6) . ?
C11 C12 1.407(7) . ?
C11 H11 0.9500 . ?
C12 C13 1.396(8) . ?
C12 H12 0.9500 . ?
C13 C14 1.363(8) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?

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
O14 Eu1 O13 79.58(10) 4_475 4_475 ?
O14 Eu1 O15 145.91(10) 4_475 1_454 ?
O13 Eu1 O15 80.37(10) 4_475 1_454 ?
O14 Eu1 O1 140.51(10) 4_475 . ?
O13 Eu1 O1 122.70(10) 4_475 . ?
O15 Eu1 O1 73.51(10) 1_454 . ?
O14 Eu1 O5 85.51(10) 4_475 . ?
O13 Eu1 O5 72.75(10) 4_475 . ?
O15 Eu1 O5 114.21(10) 1_454 . ?
O1 Eu1 O5 73.21(11) . . ?
O14 Eu1 O7 103.87(10) 4_475 . ?
O13 Eu1 O7 143.84(10) 4_475 . ?
O15 Eu1 O7 77.58(10) 1_454 . ?
O1 Eu1 O7 77.46(10) . . ?
O5 Eu1 O7 142.91(10) . . ?
O14 Eu1 O2 76.33(10) 4_475 . ?
O13 Eu1 O2 140.28(10) 4_475 . ?
O15 Eu1 O2 134.17(10) 1_454 . ?
O1 Eu1 O2 66.16(10) . . ?
O5 Eu1 O2 74.29(10) . . ?
O7 Eu1 O2 73.37(10) . . ?
O14 Eu1 O6 75.24(10) 4_475 . ?
O13 Eu1 O6 72.61(10) 4_475 . ?
O15 Eu1 O6 72.59(10) 1_454 . ?
O1 Eu1 O6 139.16(10) . . ?
O5 Eu1 O6 142.77(10) . . ?
O7 Eu1 O6 73.62(10) . . ?
O2 Eu1 O6 129.03(10) . . ?
O14 Eu1 C6 147.25(10) 4_475 1_454 ?
O13 Eu1 C6 69.76(10) 4_475 1_454 ?
O15 Eu1 C6 18.73(10) 1_454 1_454 ?
O1 Eu1 C6 69.53(10) . 1_454 ?
O5 Eu1 C6 95.87(10) . 1_454 ?
O7 Eu1 C6 94.64(10) . 1_454 ?
O2 Eu1 C6 135.59(10) . 1_454 ?
O6 Eu1 C6 84.64(10) . 1_454 ?
O14 Eu1 C1 122.34(10) 4_475 . ?
O13 Eu1 C1 135.09(10) 4_475 . ?
O15 Eu1 C1 91.13(10) 1_454 . ?
O1 Eu1 C1 19.01(10) . . ?
O5 Eu1 C1 70.99(10) . . ?
O7 Eu1 C1 73.85(10) . . ?
O2 Eu1 C1 47.15(10) . . ?
O6 Eu1 C1 146.04(10) . . ?
C6 Eu1 C1 88.50(10) 1_454 . ?
O4 Eu2 O9 132.48(9) . 3_665 ?
O4 Eu2 O8 67.46(10) . . ?
O9 Eu2 O8 66.91(9) 3_665 . ?
O4 Eu2 O10 81.96(10) . . ?
O9 Eu2 O10 73.73(10) 3_665 . ?
O8 Eu2 O10 74.28(10) . . ?
O4 Eu2 N2 137.43(10) . . ?
O9 Eu2 N2 81.64(10) 3_665 . ?
O8 Eu2 N2 124.96(11) . . ?
O10 Eu2 N2 138.86(10) . . ?
O4 Eu2 O11 71.61(10) . 3_565 ?
O9 Eu2 O11 128.98(9) 3_665 3_565 ?
O8 Eu2 O11 125.78(10) . 3_565 ?
O10 Eu2 O11 66.05(10) . 3_565 ?
N2 Eu2 O11 109.21(11) . 3_565 ?
O4 Eu2 O12 91.10(10) . . ?
O9 Eu2 O12 86.23(10) 3_665 . ?
O8 Eu2 O12 70.92(9) . . ?
O10 Eu2 O12 144.48(10) . . ?
N2 Eu2 O12 62.72(10) . . ?
O11 Eu2 O12 143.83(9) 3_565 . ?
O4 Eu2 O3 66.32(9) . . ?
O9 Eu2 O3 154.68(9) 3_665 . ?
O8 Eu2 O3 121.07(9) . . ?
O10 Eu2 O3 130.69(9) . . ?
N2 Eu2 O3 74.50(10) . . ?
O11 Eu2 O3 68.52(9) 3_565 . ?
O12 Eu2 O3 75.49(9) . . ?
O4 Eu2 N1 139.32(10) . . ?
O9 Eu2 N1 77.72(10) 3_665 . ?
O8 Eu2 N1 141.99(10) . . ?
O10 Eu2 N1 83.07(10) . . ?
N2 Eu2 N1 59.48(10) . . ?
O11 Eu2 N1 67.74(10) 3_565 . ?
O12 Eu2 N1 121.52(10) . . ?
O3 Eu2 N1 96.86(10) . . ?
O4 Eu2 C1 20.89(10) . . ?
O9 Eu2 C1 152.97(10) 3_665 . ?
O8 Eu2 C1 88.16(10) . . ?
O10 Eu2 C1 90.10(10) . . ?
N2 Eu2 C1 123.10(11) . . ?
O11 Eu2 C1 57.63(10) 3_565 . ?
O12 Eu2 C1 95.61(10) . . ?
O3 Eu2 C1 48.70(10) . . ?
N1 Eu2 C1 122.51(10) . . ?
O4 Eu2 C4 85.33(9) . . ?
O9 Eu2 C4 47.78(9) 3_665 . ?
O8 Eu2 C4 19.72(9) . . ?
O10 Eu2 C4 67.24(10) . . ?
N2 Eu2 C4 117.36(11) . . ?
O11 Eu2 C4 130.02(10) 3_565 . ?
O12 Eu2 C4 77.53(9) . . ?
O3 Eu2 C4 139.97(9) . . ?
N1 Eu2 C4 122.50(10) . . ?
C1 Eu2 C4 106.22(10) . . ?
O4 Eu2 C2 47.65(10) . . ?
O9 Eu2 C2 173.12(10) 3_665 . ?
O8 Eu2 C2 110.67(10) . . ?
O10 Eu2 C2 112.21(10) . . ?
N2 Eu2 C2 95.20(11) . . ?
O11 Eu2 C2 57.82(10) 3_565 . ?
O12 Eu2 C2 86.89(10) . . ?
O3 Eu2 C2 20.84(10) . . ?
N1 Eu2 C2 106.00(10) . . ?
C1 Eu2 C2 28.39(10) . . ?
C4 Eu2 C2 130.27(10) . . ?
C14 N1 C10 117.4(4) . . ?
C14 N1 Eu2 124.0(3) . . ?
C10 N1 Eu2 117.5(3) . . ?
C9 N2 C7 107.1(3) . . ?
C9 N2 Eu2 129.8(3) . . ?
C7 N2 Eu2 123.0(3) . . ?
C9 N3 C8 108.5(3) . . ?
C9 N3 H3 121.0 . . ?
C8 N3 H3 129.4 . . ?
C1 O1 Eu1 122.0(3) . . ?
C2 O2 Eu1 119.3(3) . . ?
C2 O3 Eu2 113.9(3) . . ?
C1 O4 Eu2 115.4(3) . . ?
Eu1 O5 H5A 112.9 . . ?
Eu1 O5 H5B 116.9 . . ?
H5A O5 H5B 107.2 . . ?
Eu1 O6 H6A 117.6 . . ?
Eu1 O6 H6B 118.8 . . ?
H6A O6 H6B 107.1 . . ?
Eu1 O7 H7A 121.3 . . ?
Eu1 O7 H7B 121.9 . . ?
H7A O7 H7B 107.5 . . ?
C4 O8 Eu2 118.7(3) . . ?
C4 O9 Eu2 118.5(2) . 3_665 ?
C3 O10 Eu2 118.0(2) . . ?
C3 O11 Eu2 117.6(2) . 3_565 ?
C5 O12 Eu2 125.1(2) . . ?
C5 O13 Eu1 147.7(3) . 4_676 ?
C6 O14 Eu1 148.4(3) . 4_676 ?
C6 O15 Eu1 123.9(3) . 1_656 ?
H16A O16 H16B 106.8(18) . . ?
H17A O17 H17B 106.9(18) . . ?
O4 C1 O1 127.4(4) . . ?
O4 C1 C2 116.4(4) . . ?
O1 C1 C2 116.1(3) . . ?
O4 C1 Eu2 43.75(19) . . ?
O1 C1 Eu2 153.6(3) . . ?
C2 C1 Eu2 78.3(2) . . ?
O4 C1 Eu1 166.4(3) . . ?
O1 C1 Eu1 39.04(19) . . ?
C2 C1 Eu1 77.1(2) . . ?
Eu2 C1 Eu1 147.76(14) . . ?
O2 C2 O3 127.4(4) . . ?
O2 C2 C1 115.7(3) . . ?
O3 C2 C1 116.8(3) . . ?
O2 C2 Eu2 163.8(3) . . ?
O3 C2 Eu2 45.27(19) . . ?
C1 C2 Eu2 73.4(2) . . ?
O11 C3 O10 126.7(4) . . ?
O11 C3 C3 117.2(4) . 3_565 ?
O10 C3 C3 116.0(4) . 3_565 ?
O11 C3 Eu2 42.37(19) . 3_565 ?
O10 C3 Eu2 162.9(3) . 3_565 ?
C3 C3 Eu2 76.3(3) 3_565 3_565 ?
O11 C3 Eu2 163.0(3) . . ?
O10 C3 Eu2 41.81(18) . . ?
C3 C3 Eu2 76.1(3) 3_565 . ?
Eu2 C3 Eu2 152.36(13) 3_565 . ?
O8 C4 O9 126.3(4) . . ?
O8 C4 C4 117.4(4) . 3_665 ?
O9 C4 C4 116.2(4) . 3_665 ?
O8 C4 Eu2 41.6(2) . . ?
O9 C4 Eu2 165.3(3) . . ?
C4 C4 Eu2 76.6(3) 3_665 . ?
O8 C4 Eu2 165.0(3) . 3_665 ?
O9 C4 Eu2 41.35(18) . 3_665 ?
C4 C4 Eu2 75.5(3) 3_665 3_665 ?
Eu2 C4 Eu2 152.17(13) . 3_665 ?
O13 C5 O12 123.4(4) . . ?
O13 C5 C7 122.7(4) . . ?
O12 C5 C7 113.9(3) . . ?
O14 C6 O15 125.1(4) . . ?
O14 C6 C8 119.8(4) . . ?
O15 C6 C8 115.1(4) . . ?
O14 C6 Eu1 88.0(2) . 1_656 ?
O15 C6 Eu1 37.34(18) . 1_656 ?
C8 C6 Eu1 151.8(3) . 1_656 ?
N2 C7 C8 109.0(3) . . ?
N2 C7 C5 114.3(3) . . ?
C8 C7 C5 136.6(4) . . ?
C7 C8 N3 104.9(3) . . ?
C7 C8 C6 135.7(4) . . ?
N3 C8 C6 119.3(3) . . ?
N2 C9 N3 110.4(3) . . ?
N2 C9 C10 119.9(4) . . ?
N3 C9 C10 129.7(4) . . ?
N1 C10 C11 123.6(4) . . ?
N1 C10 C9 111.9(4) . . ?
C11 C10 C9 124.5(4) . . ?
C10 C11 C12 117.2(5) . . ?
C10 C11 H11 121.4 . . ?
C12 C11 H11 121.4 . . ?
C13 C12 C11 118.8(5) . . ?
C13 C12 H12 120.6 . . ?
C11 C12 H12 120.6 . . ?
C14 C13 C12 119.8(5) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
N1 C14 C13 123.0(5) . . ?
N1 C14 H14 118.5 . . ?
C13 C14 H14 118.5 . . ?

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
Eu2 O4 C1 O1 -146.3(4) . . . . ?
Eu2 O4 C1 C2 32.0(4) . . . . ?
Eu2 O4 C1 Eu1 -152.1(11) . . . . ?
Eu1 O1 C1 O4 -177.8(3) . . . . ?
Eu1 O1 C1 C2 3.9(5) . . . . ?
Eu1 O1 C1 Eu2 122.4(5) . . . . ?
Eu1 O2 C2 O3 -168.7(3) . . . . ?
Eu1 O2 C2 C1 9.7(4) . . . . ?
Eu1 O2 C2 Eu2 -111.6(10) . . . . ?
Eu2 O3 C2 O2 160.7(3) . . . . ?
Eu2 O3 C2 C1 -17.6(4) . . . . ?
O4 C1 C2 O2 172.5(4) . . . . ?
O1 C1 C2 O2 -9.1(5) . . . . ?
Eu2 C1 C2 O2 -165.6(3) . . . . ?
Eu1 C1 C2 O2 -6.6(3) . . . . ?
O4 C1 C2 O3 -9.0(5) . . . . ?
O1 C1 C2 O3 169.4(4) . . . . ?
Eu2 C1 C2 O3 13.0(3) . . . . ?
Eu1 C1 C2 O3 172.0(3) . . . . ?
O4 C1 C2 Eu2 -22.0(3) . . . . ?
O1 C1 C2 Eu2 156.5(3) . . . . ?
Eu1 C1 C2 Eu2 159.00(10) . . . . ?
Eu2 O11 C3 O10 162.2(3) 3_565 . . . ?
Eu2 O11 C3 C3 -16.5(5) 3_565 . . 3_565 ?
Eu2 O11 C3 Eu2 -155.6(8) 3_565 . . . ?
Eu2 O10 C3 O11 162.9(3) . . . . ?
Eu2 O10 C3 C3 -18.5(5) . . . 3_565 ?
Eu2 O10 C3 Eu2 -152.4(8) . . . 3_565 ?
Eu2 O8 C4 O9 168.7(3) . . . . ?
Eu2 O8 C4 C4 -12.1(6) . . . 3_665 ?
Eu2 O8 C4 Eu2 -160.0(9) . . . 3_665 ?
Eu2 O9 C4 O8 168.2(3) 3_665 . . . ?
Eu2 O9 C4 C4 -11.1(5) 3_665 . . 3_665 ?
Eu2 O9 C4 Eu2 -160.8(9) 3_665 . . . ?
Eu1 O13 C5 O12 165.9(3) 4_676 . . . ?
Eu1 O13 C5 C7 -14.6(7) 4_676 . . . ?
Eu2 O12 C5 O13 -170.0(3) . . . . ?
Eu2 O12 C5 C7 10.4(5) . . . . ?
Eu1 O14 C6 O15 -137.6(4) 4_676 . . . ?
Eu1 O14 C6 C8 41.3(7) 4_676 . . . ?
Eu1 O14 C6 Eu1 -133.4(4) 4_676 . . 1_656 ?
Eu1 O15 C6 O14 7.0(5) 1_656 . . . ?
Eu1 O15 C6 C8 -172.0(2) 1_656 . . . ?
C9 N2 C7 C8 -0.4(4) . . . . ?
Eu2 N2 C7 C8 176.8(2) . . . . ?
C9 N2 C7 C5 178.8(3) . . . . ?
Eu2 N2 C7 C5 -4.0(4) . . . . ?
O13 C5 C7 N2 176.5(4) . . . . ?
O12 C5 C7 N2 -3.9(5) . . . . ?
O13 C5 C7 C8 -4.6(7) . . . . ?
O12 C5 C7 C8 175.0(4) . . . . ?
N2 C7 C8 N3 0.2(4) . . . . ?
C5 C7 C8 N3 -178.7(4) . . . . ?
N2 C7 C8 C6 -176.6(4) . . . . ?
C5 C7 C8 C6 4.5(8) . . . . ?
C9 N3 C8 C7 0.0(4) . . . . ?
C9 N3 C8 C6 177.5(3) . . . . ?
O14 C6 C8 C7 -9.1(7) . . . . ?
O15 C6 C8 C7 170.0(4) . . . . ?
Eu1 C6 C8 C7 159.6(4) 1_656 . . . ?
O14 C6 C8 N3 174.4(3) . . . . ?
O15 C6 C8 N3 -6.5(5) . . . . ?
Eu1 C6 C8 N3 -16.9(7) 1_656 . . . ?
C7 N2 C9 N3 0.4(4) . . . . ?
Eu2 N2 C9 N3 -176.6(2) . . . . ?
C7 N2 C9 C10 179.5(3) . . . . ?
Eu2 N2 C9 C10 2.5(5) . . . . ?
C8 N3 C9 N2 -0.2(5) . . . . ?
C8 N3 C9 C10 -179.2(4) . . . . ?
C14 N1 C10 C11 -1.7(6) . . . . ?
Eu2 N1 C10 C11 166.9(3) . . . . ?
C14 N1 C10 C9 178.3(4) . . . . ?
Eu2 N1 C10 C9 -13.0(4) . . . . ?
N2 C9 C10 N1 8.1(5) . . . . ?
N3 C9 C10 N1 -173.0(4) . . . . ?
N2 C9 C10 C11 -171.8(4) . . . . ?
N3 C9 C10 C11 7.1(7) . . . . ?
N1 C10 C11 C12 1.9(7) . . . . ?
C9 C10 C11 C12 -178.3(4) . . . . ?
C10 C11 C12 C13 0.5(7) . . . . ?
C11 C12 C13 C14 -2.8(7) . . . . ?
C10 N1 C14 C13 -0.8(7) . . . . ?
Eu2 N1 C14 C13 -168.6(4) . . . . ?
C12 C13 C14 N1 3.0(8) . . . . ?

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
O17 H17B O6 0.821(10) 2.225(12) 3.045(5) 176(6) 3_565
O17 H17A O3 0.822(10) 2.045(13) 2.863(4) 173(5) 2_645
O16 H16B O17 0.821(10) 2.12(3) 2.884(5) 155(6) 4_566
O16 H16A O4 0.820(10) 2.11(3) 2.875(5) 156(6) 3_665
O7 H7B O12 0.82 2.07 2.806(4) 149.9 1_455
O7 H7A O10 0.82 1.99 2.801(4) 171.6 3_565
O6 H6B O12 0.82 2.00 2.747(4) 151.5 1_455
O6 H6A O16 0.82 1.94 2.759(5) 171.6 3_565
O5 H5B O17 0.82 2.06 2.816(5) 153.3 3_665
O5 H5A O2 0.82 1.92 2.736(4) 171.7 4_575
N3 H3 O9 0.86 2.09 2.906(4) 158.5 1_556

_refine_diff_density_max         1.946
_refine_diff_density_min         -2.542
_refine_diff_density_rms         0.211

####################################################################### 
# 
# 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_Z5-Sm-zb40-14R1
_database_code_depnum_ccdc_archive 'CCDC 1506101'
_audit_update_record             
;
2017-02-28 deposited with the CCDC.
2017-03-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H14.75 N3 O17 Sm2'
_chemical_formula_weight         797.74

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sm Sm -0.1030 3.5380 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   9.5900(19)
_cell_length_b                   22.621(5)
_cell_length_c                   10.129(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.61(3)
_cell_angle_gamma                90
_cell_volume                     2152.4(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    10581
_cell_measurement_theta_min      2.08
_cell_measurement_theta_max      29.55

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.462
_exptl_crystal_F_000             1519
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    5.667
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3684
_exptl_absorpt_correction_T_max  0.5694
_exptl_absorpt_process_details   '(HKL SCALEPACK; Otwinowski & Minor, 1997)'

_exptl_special_details           ?

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.720
_diffrn_radiation_type           synchrotron
_diffrn_source                   'synchrotron, 3W1A at BSRF'
_diffrn_measurement_device_type  mar165
_diffrn_measurement_method       'oscillation mode'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7064
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.196
_diffrn_reflns_theta_max         25.497
_diffrn_reflns_theta_full        25.497
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3843
_reflns_number_gt                3697
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0256P)²+3.1145P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3843
_refine_ls_number_parameters     327
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0250
_refine_ls_R_factor_gt           0.0243
_refine_ls_wR_factor_ref         0.0568
_refine_ls_wR_factor_gt          0.0563
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Sm1 Sm 1.24947(2) 0.27703(2) 1.04694(2) 0.01362(7) Uani 1 1 d . . . . .
Sm2 Sm 0.72018(2) 0.43443(2) 0.85643(2) 0.01027(7) Uani 1 1 d . . . . .
N1 N 0.5989(3) 0.41469(13) 0.6207(3) 0.0126(5) Uani 1 1 d . . . . .
N2 N 0.5339(3) 0.41381(13) 0.4008(3) 0.0164(6) Uani 1 1 d . . . . .
H2 H 0.523237 0.422615 0.316652 0.020 Uiso 1 1 d R U . . .
N3 N 0.7742(3) 0.50658(14) 0.6422(3) 0.0195(6) Uani 1 1 d . . . . .
O1 O 1.0650(3) 0.33834(13) 1.1094(2) 0.0259(6) Uani 1 1 d . . . . .
O2 O 1.0333(3) 0.28809(12) 0.8657(2) 0.0244(6) Uani 1 1 d . . . . .
O3 O 0.8335(3) 0.34115(12) 0.7955(2) 0.0232(6) Uani 1 1 d . . . . .
O4 O 0.8505(3) 0.38014(14) 1.0494(2) 0.0280(6) Uani 1 1 d . . . . .
O5 O 0.5236(2) 0.35958(11) 0.8170(2) 0.0191(5) Uani 1 1 d . . . . .
O6 O 0.3780(3) 0.29633(12) 0.6896(2) 0.0228(6) Uani 1 1 d . . . . .
O7 O 0.2789(3) 0.29513(11) 0.3888(2) 0.0215(5) Uani 1 1 d . . . . .
O8 O 0.3682(3) 0.33901(12) 0.2274(2) 0.0227(5) Uani 1 1 d . . . . .
O9 O 0.5986(3) 0.43630(11) 1.0496(2) 0.0192(5) Uani 1 1 d . . . . .
O10 O 0.4682(2) 0.49065(11) 1.1637(2) 0.0170(5) Uani 1 1 d . . . . .
O11 O 0.9786(2) 0.44933(12) 0.8682(2) 0.0207(5) Uani 1 1 d . . . . .
O12 O 1.1774(2) 0.48099(12) 1.0040(3) 0.0224(5) Uani 1 1 d . . . . .
O13 O 1.2775(3) 0.37089(12) 0.9320(3) 0.0267(6) Uani 1 1 d . . . . .
H13A H 1.229160 0.400282 0.938288 0.040 Uiso 1 1 d R U . . .
H13B H 1.353255 0.381916 0.914822 0.040 Uiso 1 1 d R U . . .
O14 O 1.5060(3) 0.28440(14) 1.0266(3) 0.0329(7) Uani 1 1 d . . . . .
H14A H 1.555468 0.303939 1.086396 0.049 Uiso 1 1 d R U . . .
H14B H 1.524270 0.295585 0.954938 0.049 Uiso 1 1 d R U . . .
O15 O 1.0766(3) 0.20926(14) 1.1072(3) 0.0314(6) Uani 1 1 d . . . . .
H15A H 0.993810 0.213526 1.067633 0.047 Uiso 1 1 d R U . . .
H15B H 1.076086 0.204322 1.187262 0.047 Uiso 1 1 d R U . . .
O16 O 0.7252(7) 0.1750(5) 0.7507(6) 0.120(4) Uani 0.870(18) 1 d . U P . .
O17 O 0.7817(5) 0.2131(3) 0.0261(6) 0.0956(18) Uani 1 1 d . . . . .
C1 C 0.4573(3) 0.36966(15) 0.4468(3) 0.0129(6) Uani 1 1 d . . . . .
C2 C 0.4996(3) 0.37089(14) 0.5862(3) 0.0123(6) Uani 1 1 d . . . . .
C3 C 0.6187(3) 0.43971(15) 0.5080(3) 0.0139(7) Uani 1 1 d . . . . .
C4 C 0.7213(3) 0.48841(16) 0.5143(3) 0.0167(7) Uani 1 1 d . . . . .
C5 C 0.7616(4) 0.51294(19) 0.4011(4) 0.0273(8) Uani 1 1 d . . . . .
H5 H 0.724385 0.498333 0.313179 0.033 Uiso 1 1 calc R U . . .
C6 C 0.8586(5) 0.5597(2) 0.4219(5) 0.0357(10) Uani 1 1 d . . . . .
H6 H 0.888897 0.577804 0.347784 0.043 Uiso 1 1 calc R U . . .
C7 C 0.9098(4) 0.57925(19) 0.5516(4) 0.0346(10) Uani 1 1 d . . . . .
H7 H 0.974287 0.611557 0.567596 0.041 Uiso 1 1 calc R U . . .
C8 C 0.8667(4) 0.55152(18) 0.6577(4) 0.0281(8) Uani 1 1 d . . . . .
H8 H 0.904639 0.565028 0.746445 0.034 Uiso 1 1 calc R U . . .
C9 C 0.3606(3) 0.33164(15) 0.3484(3) 0.0140(6) Uani 1 1 d . . . . .
C10 C 0.4625(3) 0.33891(15) 0.7031(3) 0.0133(6) Uani 1 1 d . . . . .
C11 C 0.5198(3) 0.47870(14) 1.0610(3) 0.0117(6) Uani 1 1 d . . . . .
C12 C 1.0446(3) 0.47983(14) 0.9623(3) 0.0149(7) Uani 1 1 d . . . . .
C13 C 0.9523(4) 0.34923(16) 1.0276(3) 0.0187(7) Uani 1 1 d . . . . .
C14 C 0.9376(4) 0.32376(16) 0.8826(3) 0.0182(7) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Sm1 O7 2.344(3) 4_666 ?
Sm1 O6 2.376(2) 4_666 ?
Sm1 O8 2.401(2) 1_656 ?
Sm1 O15 2.424(3) . ?
Sm1 O1 2.430(3) . ?
Sm1 O13 2.462(3) . ?
Sm1 O2 2.489(2) . ?
Sm1 O14 2.515(3) . ?
Sm2 O4 2.430(3) . ?
Sm2 O10 2.456(2) 3_667 ?
Sm2 O12 2.463(2) 3_767 ?
Sm2 O9 2.472(3) . ?
Sm2 N1 2.477(3) . ?
Sm2 O11 2.480(2) . ?
Sm2 O5 2.506(2) . ?
Sm2 O3 2.507(3) . ?
Sm2 N3 2.845(3) . ?
N1 C3 1.322(4) . ?
N1 C2 1.370(4) . ?
N2 C3 1.352(4) . ?
N2 C1 1.376(4) . ?
N2 H2 0.8609 . ?
N3 C8 1.338(5) . ?
N3 C4 1.356(4) . ?
O1 C13 1.247(4) . ?
O2 C14 1.259(4) . ?
O3 C14 1.255(4) . ?
O4 C13 1.255(4) . ?
O5 C10 1.273(4) . ?
O6 C10 1.248(4) . ?
O7 C9 1.262(4) . ?
O8 C9 1.253(4) . ?
O9 C11 1.241(4) . ?
O10 C11 1.268(4) . ?
O11 C12 1.242(4) . ?
O12 C12 1.259(4) . ?
O13 H13A 0.8200 . ?
O13 H13B 0.8198 . ?
O14 H14A 0.8198 . ?
O14 H14B 0.8200 . ?
O15 H15A 0.8200 . ?
O15 H15B 0.8201 . ?
C1 C2 1.389(4) . ?
C1 C9 1.491(4) . ?
C2 C10 1.490(5) . ?
C3 C4 1.470(5) . ?
C4 C5 1.397(5) . ?
C5 C6 1.397(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.379(6) . ?
C6 H6 0.9500 . ?
C7 C8 1.378(6) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C11 C11 1.553(6) 3_667 ?
C12 C12 1.553(7) 3_767 ?
C13 C14 1.558(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O7 Sm1 O6 79.06(9) 4_666 4_666 ?
O7 Sm1 O8 145.40(9) 4_666 1_656 ?
O6 Sm1 O8 80.59(9) 4_666 1_656 ?
O7 Sm1 O15 85.08(10) 4_666 . ?
O6 Sm1 O15 72.69(10) 4_666 . ?
O8 Sm1 O15 114.90(9) 1_656 . ?
O7 Sm1 O1 140.34(8) 4_666 . ?
O6 Sm1 O1 123.78(9) 4_666 . ?
O8 Sm1 O1 74.15(9) 1_656 . ?
O15 Sm1 O1 74.03(11) . . ?
O7 Sm1 O13 103.76(9) 4_666 . ?
O6 Sm1 O13 142.89(9) 4_666 . ?
O8 Sm1 O13 77.07(9) 1_656 . ?
O15 Sm1 O13 144.04(9) . . ?
O1 Sm1 O13 77.59(9) . . ?
O7 Sm1 O2 76.30(8) 4_666 . ?
O6 Sm1 O2 140.51(9) 4_666 . ?
O8 Sm1 O2 134.38(9) 1_656 . ?
O15 Sm1 O2 74.87(10) . . ?
O1 Sm1 O2 65.96(8) . . ?
O13 Sm1 O2 73.66(9) . . ?
O7 Sm1 O14 74.67(10) 4_666 . ?
O6 Sm1 O14 72.55(9) 4_666 . ?
O8 Sm1 O14 72.67(10) 1_656 . ?
O15 Sm1 O14 142.39(10) . . ?
O1 Sm1 O14 139.36(10) . . ?
O13 Sm1 O14 72.69(9) . . ?
O2 Sm1 O14 128.02(9) . . ?
O4 Sm2 O10 131.79(8) . 3_667 ?
O4 Sm2 O12 81.37(10) . 3_767 ?
O10 Sm2 O12 73.35(8) 3_667 3_767 ?
O4 Sm2 O9 67.69(8) . . ?
O10 Sm2 O9 66.27(8) 3_667 . ?
O12 Sm2 O9 74.31(9) 3_767 . ?
O4 Sm2 N1 138.56(10) . . ?
O10 Sm2 N1 81.34(8) 3_667 . ?
O12 Sm2 N1 138.51(9) 3_767 . ?
O9 Sm2 N1 124.15(9) . . ?
O4 Sm2 O11 71.51(9) . . ?
O10 Sm2 O11 128.43(9) 3_667 . ?
O12 Sm2 O11 65.64(8) 3_767 . ?
O9 Sm2 O11 125.86(8) . . ?
N1 Sm2 O11 109.97(9) . . ?
O4 Sm2 O5 92.02(9) . . ?
O10 Sm2 O5 86.32(9) 3_667 . ?
O12 Sm2 O5 144.79(8) 3_767 . ?
O9 Sm2 O5 71.21(8) . . ?
N1 Sm2 O5 62.11(8) . . ?
O11 Sm2 O5 144.29(9) . . ?
O4 Sm2 O3 66.07(8) . . ?
O10 Sm2 O3 155.32(8) 3_667 . ?
O12 Sm2 O3 130.74(8) 3_767 . ?
O9 Sm2 O3 120.42(9) . . ?
N1 Sm2 O3 75.73(8) . . ?
O11 Sm2 O3 69.37(8) . . ?
O5 Sm2 O3 75.02(9) . . ?
O4 Sm2 N3 139.48(8) . . ?
O10 Sm2 N3 77.56(8) 3_667 . ?
O12 Sm2 N3 83.06(9) 3_767 . ?
O9 Sm2 N3 141.39(8) . . ?
N1 Sm2 N3 59.37(8) . . ?
O11 Sm2 N3 67.98(8) . . ?
O5 Sm2 N3 120.85(8) . . ?
O3 Sm2 N3 98.08(9) . . ?
C3 N1 C2 107.6(3) . . ?
C3 N1 Sm2 129.4(2) . . ?
C2 N1 Sm2 122.9(2) . . ?
C3 N2 C1 108.6(3) . . ?
C3 N2 H2 128.8 . . ?
C1 N2 H2 122.6 . . ?
C8 N3 C4 117.0(3) . . ?
C8 N3 Sm2 124.4(2) . . ?
C4 N3 Sm2 117.7(2) . . ?
C13 O1 Sm1 121.3(2) . . ?
C14 O2 Sm1 119.1(2) . . ?
C14 O3 Sm2 114.4(2) . . ?
C13 O4 Sm2 115.6(2) . . ?
C10 O5 Sm2 125.9(2) . . ?
C10 O6 Sm1 148.3(2) . 4_465 ?
C9 O7 Sm1 147.8(2) . 4_465 ?
C9 O8 Sm1 123.7(2) . 1_454 ?
C11 O9 Sm2 118.7(2) . . ?
C11 O10 Sm2 118.8(2) . 3_667 ?
C12 O11 Sm2 117.5(2) . . ?
C12 O12 Sm2 118.0(2) . 3_767 ?
Sm1 O13 H13A 123.1 . . ?
Sm1 O13 H13B 123.3 . . ?
H13A O13 H13B 108.0 . . ?
Sm1 O14 H14A 113.9 . . ?
Sm1 O14 H14B 118.7 . . ?
H14A O14 H14B 107.0 . . ?
Sm1 O15 H15A 116.5 . . ?
Sm1 O15 H15B 118.4 . . ?
H15A O15 H15B 107.5 . . ?
N2 C1 C2 105.3(3) . . ?
N2 C1 C9 119.7(3) . . ?
C2 C1 C9 135.0(3) . . ?
N1 C2 C1 108.6(3) . . ?
N1 C2 C10 114.4(3) . . ?
C1 C2 C10 136.9(3) . . ?
N1 C3 N2 109.9(3) . . ?
N1 C3 C4 119.6(3) . . ?
N2 C3 C4 130.5(3) . . ?
N3 C4 C5 123.5(3) . . ?
N3 C4 C3 112.8(3) . . ?
C5 C4 C3 123.7(3) . . ?
C6 C5 C4 117.6(4) . . ?
C6 C5 H5 121.2 . . ?
C4 C5 H5 121.2 . . ?
C7 C6 C5 119.0(4) . . ?
C7 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C8 C7 C6 119.5(4) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
N3 C8 C7 123.4(4) . . ?
N3 C8 H8 118.3 . . ?
C7 C8 H8 118.3 . . ?
O8 C9 O7 124.5(3) . . ?
O8 C9 C1 115.2(3) . . ?
O7 C9 C1 120.3(3) . . ?
O6 C10 O5 123.5(3) . . ?
O6 C10 C2 122.8(3) . . ?
O5 C10 C2 113.7(3) . . ?
O9 C11 O10 125.9(3) . . ?
O9 C11 C11 117.5(3) . 3_667 ?
O10 C11 C11 116.6(3) . 3_667 ?
O11 C12 O12 126.5(3) . . ?
O11 C12 C12 117.3(3) . 3_767 ?
O12 C12 C12 116.2(3) . 3_767 ?
O1 C13 O4 126.5(3) . . ?
O1 C13 C14 117.1(3) . . ?
O4 C13 C14 116.4(3) . . ?
O3 C14 O2 127.1(3) . . ?
O3 C14 C13 117.1(3) . . ?
O2 C14 C13 115.8(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N2 C1 C2 0.5(4) . . . . ?
C3 N2 C1 C9 -176.7(3) . . . . ?
C3 N1 C2 C1 -0.3(4) . . . . ?
Sm2 N1 C2 C1 -177.3(2) . . . . ?
C3 N1 C2 C10 -178.7(3) . . . . ?
Sm2 N1 C2 C10 4.3(4) . . . . ?
N2 C1 C2 N1 -0.2(4) . . . . ?
C9 C1 C2 N1 176.4(3) . . . . ?
N2 C1 C2 C10 177.8(4) . . . . ?
C9 C1 C2 C10 -5.6(7) . . . . ?
C2 N1 C3 N2 0.6(4) . . . . ?
Sm2 N1 C3 N2 177.4(2) . . . . ?
C2 N1 C3 C4 -179.7(3) . . . . ?
Sm2 N1 C3 C4 -2.9(5) . . . . ?
C1 N2 C3 N1 -0.7(4) . . . . ?
C1 N2 C3 C4 179.6(3) . . . . ?
C8 N3 C4 C5 1.9(5) . . . . ?
Sm2 N3 C4 C5 -167.4(3) . . . . ?
C8 N3 C4 C3 -178.9(3) . . . . ?
Sm2 N3 C4 C3 11.8(4) . . . . ?
N1 C3 C4 N3 -6.9(4) . . . . ?
N2 C3 C4 N3 172.7(3) . . . . ?
N1 C3 C4 C5 172.3(4) . . . . ?
N2 C3 C4 C5 -8.1(6) . . . . ?
N3 C4 C5 C6 -1.8(6) . . . . ?
C3 C4 C5 C6 179.0(4) . . . . ?
C4 C5 C6 C7 0.1(6) . . . . ?
C5 C6 C7 C8 1.4(7) . . . . ?
C4 N3 C8 C7 -0.3(6) . . . . ?
Sm2 N3 C8 C7 168.3(3) . . . . ?
C6 C7 C8 N3 -1.3(7) . . . . ?
Sm1 O8 C9 O7 -7.7(5) 1_454 . . . ?
Sm1 O8 C9 C1 172.1(2) 1_454 . . . ?
Sm1 O7 C9 O8 136.9(3) 4_465 . . . ?
Sm1 O7 C9 C1 -42.9(6) 4_465 . . . ?
N2 C1 C9 O8 7.5(5) . . . . ?
C2 C1 C9 O8 -168.7(4) . . . . ?
N2 C1 C9 O7 -172.7(3) . . . . ?
C2 C1 C9 O7 11.1(6) . . . . ?
Sm1 O6 C10 O5 -166.4(3) 4_465 . . . ?
Sm1 O6 C10 C2 14.5(6) 4_465 . . . ?
Sm2 O5 C10 O6 170.5(2) . . . . ?
Sm2 O5 C10 C2 -10.3(4) . . . . ?
N1 C2 C10 O6 -177.2(3) . . . . ?
C1 C2 C10 O6 4.9(6) . . . . ?
N1 C2 C10 O5 3.6(4) . . . . ?
C1 C2 C10 O5 -174.3(4) . . . . ?
Sm2 O9 C11 O10 -168.4(2) . . . . ?
Sm2 O9 C11 C11 11.6(4) . . . 3_667 ?
Sm2 O10 C11 O9 -168.3(2) 3_667 . . . ?
Sm2 O10 C11 C11 11.7(4) 3_667 . . 3_667 ?
Sm2 O11 C12 O12 161.9(3) . . . . ?
Sm2 O11 C12 C12 -17.3(5) . . . 3_767 ?
Sm2 O12 C12 O11 162.2(3) 3_767 . . . ?
Sm2 O12 C12 C12 -18.6(5) 3_767 . . 3_767 ?
Sm1 O1 C13 O4 179.9(3) . . . . ?
Sm1 O1 C13 C14 -2.2(4) . . . . ?
Sm2 O4 C13 O1 147.8(3) . . . . ?
Sm2 O4 C13 C14 -30.1(4) . . . . ?
Sm2 O3 C14 O2 -161.2(3) . . . . ?
Sm2 O3 C14 C13 18.1(4) . . . . ?
Sm1 O2 C14 O3 168.6(3) . . . . ?
Sm1 O2 C14 C13 -10.7(4) . . . . ?
O1 C13 C14 O3 -170.6(3) . . . . ?
O4 C13 C14 O3 7.5(5) . . . . ?
O1 C13 C14 O2 8.8(5) . . . . ?
O4 C13 C14 O2 -173.1(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O15 H15B O2 0.82 1.94 2.734(4) 162.6 4_566
O15 H15A O17 0.82 1.99 2.783(6) 161.8 1_556
O14 H14B O5 0.82 2.01 2.752(4) 149.9 1_655
O14 H14A O16 0.82 2.14 2.916(8) 159.1 4_666
O13 H13B O5 0.82 2.13 2.847(4) 145.2 1_655
O13 H13A O12 0.82 2.04 2.817(4) 158.4 .
O13 H13A O11 0.82 2.61 3.322(4) 145.7 .
N2 H2 O10 0.86 2.17 2.928(4) 146.4 1_554

_refine_diff_density_max         1.728
_refine_diff_density_min         -1.675
_refine_diff_density_rms         0.153

####################################################################### 
# 
# 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_Z7-Gd-zb25-14R1
_database_code_depnum_ccdc_archive 'CCDC 1506103'
_audit_update_record             
;
2017-02-28 deposited with the CCDC.
2017-03-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H15 Gd2 N3 O17'
_chemical_formula_weight         811.79

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Gd Gd -0.1653 3.9035 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   9.5261(7)
_cell_length_b                   22.4729(16)
_cell_length_c                   10.1216(7)
_cell_angle_alpha                90
_cell_angle_beta                 102.263(2)
_cell_angle_gamma                90
_cell_volume                     2117.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5282
_cell_measurement_theta_min      2.8
_cell_measurement_theta_max      28.4

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.547
_exptl_crystal_F_000             1536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    6.306
_shelx_estimated_absorpt_T_min   0.302
_shelx_estimated_absorpt_T_max   0.302
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7636
_exptl_absorpt_correction_T_max  0.8476
_exptl_absorpt_process_details   '(HKL SCALEPACK; Otwinowski & Minor, 1997)'

_exptl_special_details           ?

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17469
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.817
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4153
_reflns_number_gt                3576
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0130P)²+3.4271P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4153
_refine_ls_number_parameters     355
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.0310
_refine_ls_R_factor_gt           0.0220
_refine_ls_wR_factor_ref         0.0427
_refine_ls_wR_factor_gt          0.0401
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Gd1 Gd 0.71895(2) 0.43454(2) 0.85846(2) 0.01256(5) Uani 1 1 d . . . . .
Gd2 Gd 1.24923(2) 0.27679(2) 1.04843(2) 0.01451(5) Uani 1 1 d . . . . .
N1 N 0.5991(3) 0.41480(14) 0.6239(3) 0.0144(7) Uani 1 1 d . . . . .
N2 N 0.5334(3) 0.41373(14) 0.4039(3) 0.0171(7) Uani 1 1 d . . . . .
H2 H 0.491622 0.410470 0.319938 0.020 Uiso 1 1 d R U . . .
N3 N 0.7745(4) 0.50730(15) 0.6454(4) 0.0231(8) Uani 1 1 d . . . . .
O1 O 1.0656(3) 0.33787(13) 1.1102(3) 0.0245(7) Uani 1 1 d . . . . .
O2 O 1.0317(3) 0.28740(13) 0.8672(3) 0.0245(7) Uani 1 1 d . . . . .
O3 O 0.8313(3) 0.34137(13) 0.7957(3) 0.0242(7) Uani 1 1 d . . . . .
O4 O 0.8494(3) 0.38033(14) 1.0494(3) 0.0259(7) Uani 1 1 d . . . . .
O5 O 0.5229(3) 0.36023(12) 0.8197(3) 0.0191(6) Uani 1 1 d . . . . .
O6 O 0.3797(3) 0.29574(13) 0.6920(3) 0.0229(7) Uani 1 1 d . . . . .
O7 O 0.2770(3) 0.29424(12) 0.3910(3) 0.0214(6) Uani 1 1 d . . . . .
O8 O 0.3675(3) 0.33745(13) 0.2298(3) 0.0212(6) Uani 1 1 d . . . . .
O9 O 0.6009(3) 0.43641(13) 1.0505(3) 0.0214(6) Uani 1 1 d . . . . .
O10 O 0.4688(3) 0.49088(12) 1.1632(3) 0.0183(6) Uani 1 1 d . . . . .
O11 O 0.9768(3) 0.44861(12) 0.8688(3) 0.0208(6) Uani 1 1 d . . . . .
O12 O 1.1782(3) 0.48116(13) 1.0032(3) 0.0241(7) Uani 1 1 d . . . . .
O13 O 1.2768(3) 0.36934(13) 0.9339(3) 0.0290(7) Uani 1 1 d D . . . .
H13A H 1.247(4) 0.4025(9) 0.948(5) 0.044 Uiso 1 1 d D U . . .
H13B H 1.351(3) 0.3739(17) 0.908(5) 0.044 Uiso 1 1 d D U . . .
O14 O 1.5044(3) 0.28355(15) 1.0285(3) 0.0315(8) Uani 1 1 d D . . . .
H14A H 1.560(4) 0.293(2) 1.098(2) 0.047 Uiso 1 1 d D U . . .
H14B H 1.526(5) 0.3024(19) 0.966(3) 0.047 Uiso 1 1 d D U . . .
O15 O 1.0799(3) 0.20926(16) 1.1097(3) 0.0317(8) Uani 1 1 d D . . . .
H15A H 0.996(2) 0.212(2) 1.068(3) 0.048 Uiso 1 1 d D U . . .
H15B H 1.077(4) 0.208(2) 1.1900(13) 0.048 Uiso 1 1 d D U . . .
O16 O 0.7256(6) 0.1731(3) 0.7549(7) 0.1065(19) Uani 1 1 d D U . . .
H16A H 0.775(8) 0.144(2) 0.748(10) 0.160 Uiso 1 1 d D U . . .
H16B H 0.774(8) 0.203(2) 0.749(11) 0.160 Uiso 1 1 d D U . . .
O17 O 0.7827(6) 0.2144(2) 0.0289(5) 0.0841(15) Uani 1 1 d D . . . .
H17A H 0.746(9) 0.223(3) -0.049(3) 0.126 Uiso 1 1 d D U . . .
H17B H 0.818(9) 0.1812(18) 0.028(7) 0.126 Uiso 1 1 d D U . . .
C1 C 0.4553(4) 0.36923(17) 0.4492(4) 0.0148(8) Uani 1 1 d . . . . .
C2 C 0.4988(4) 0.37095(17) 0.5884(4) 0.0140(8) Uani 1 1 d . . . . .
C3 C 0.6174(4) 0.43997(17) 0.5109(4) 0.0157(8) Uani 1 1 d . . . . .
C4 C 0.7219(4) 0.48852(19) 0.5169(4) 0.0192(9) Uani 1 1 d . . . . .
C5 C 0.7616(5) 0.5129(2) 0.4048(5) 0.0304(11) Uani 1 1 d . . . . .
H5 H 0.723759 0.498451 0.318506 0.036 Uiso 1 1 calc R U . . .
C6 C 0.8603(5) 0.5598(2) 0.4249(5) 0.0373(12) Uani 1 1 d . . . . .
H6 H 0.890433 0.577242 0.352409 0.045 Uiso 1 1 calc R U . . .
C7 C 0.9114(5) 0.5794(2) 0.5549(5) 0.0388(13) Uani 1 1 d . . . . .
H7 H 0.975655 0.611085 0.570931 0.047 Uiso 1 1 calc R U . . .
C8 C 0.8681(5) 0.5524(2) 0.6610(5) 0.0316(11) Uani 1 1 d . . . . .
H8 H 0.905590 0.566129 0.747998 0.038 Uiso 1 1 calc R U . . .
C9 C 0.3585(4) 0.33058(17) 0.3506(4) 0.0152(8) Uani 1 1 d . . . . .
C10 C 0.4628(4) 0.33865(17) 0.7054(4) 0.0140(8) Uani 1 1 d . . . . .
C11 C 0.5198(4) 0.47909(18) 1.0618(4) 0.0151(8) Uani 1 1 d . . . . .
C12 C 1.0446(4) 0.47944(18) 0.9623(4) 0.0179(9) Uani 1 1 d . . . . .
C13 C 0.9523(4) 0.34939(18) 1.0273(4) 0.0186(9) Uani 1 1 d . . . . .
C14 C 0.9359(4) 0.32359(18) 0.8839(4) 0.0184(9) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Gd1 O4 2.396(3) . ?
Gd1 O10 2.426(3) 3_667 ?
Gd1 O12 2.434(3) 3_767 ?
Gd1 O9 2.444(3) . ?
Gd1 N1 2.447(3) . ?
Gd1 O11 2.457(3) . ?
Gd1 O5 2.474(3) . ?
Gd1 O3 2.495(3) . ?
Gd1 N3 2.844(4) . ?
Gd2 O7 2.310(3) 4_666 ?
Gd2 O6 2.355(3) 4_666 ?
Gd2 O8 2.371(3) 1_656 ?
Gd2 O15 2.391(3) . ?
Gd2 O1 2.408(3) . ?
Gd2 O13 2.422(3) . ?
Gd2 O2 2.470(3) . ?
Gd2 O14 2.486(3) . ?
N1 C3 1.320(5) . ?
N1 C2 1.366(5) . ?
N2 C3 1.339(5) . ?
N2 C1 1.381(5) . ?
N2 H2 0.8617 . ?
N3 C8 1.337(5) . ?
N3 C4 1.358(5) . ?
O1 C13 1.246(5) . ?
O2 C14 1.261(5) . ?
O3 C14 1.254(5) . ?
O4 C13 1.260(5) . ?
O5 C10 1.273(4) . ?
O6 C10 1.237(4) . ?
O7 C9 1.254(5) . ?
O8 C9 1.253(4) . ?
O9 C11 1.252(5) . ?
O10 C11 1.254(4) . ?
O11 C12 1.238(5) . ?
O12 C12 1.253(5) . ?
O13 H13A 0.820(10) . ?
O13 H13B 0.816(10) . ?
O14 H14A 0.816(10) . ?
O14 H14B 0.820(10) . ?
O15 H15A 0.822(10) . ?
O15 H15B 0.819(10) . ?
O16 H16A 0.817(10) . ?
O16 H16B 0.821(10) . ?
O17 H17A 0.818(10) . ?
O17 H17B 0.819(10) . ?
C1 C2 1.382(5) . ?
C1 C9 1.486(5) . ?
C2 C10 1.490(5) . ?
C3 C4 1.469(5) . ?
C4 C5 1.382(6) . ?
C5 C6 1.398(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.375(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.371(7) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C11 C11 1.546(7) 3_667 ?
C12 C12 1.560(8) 3_767 ?
C13 C14 1.539(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 Gd1 O10 132.07(9) . 3_667 ?
O4 Gd1 O12 81.69(10) . 3_767 ?
O10 Gd1 O12 73.34(9) 3_667 3_767 ?
O4 Gd1 O9 67.33(9) . . ?
O10 Gd1 O9 66.76(9) 3_667 . ?
O12 Gd1 O9 74.10(10) 3_767 . ?
O4 Gd1 N1 138.21(10) . . ?
O10 Gd1 N1 81.62(10) 3_667 . ?
O12 Gd1 N1 138.34(10) 3_767 . ?
O9 Gd1 N1 125.18(10) . . ?
O4 Gd1 O11 71.86(10) . . ?
O10 Gd1 O11 128.75(9) 3_667 . ?
O12 Gd1 O11 66.35(9) 3_767 . ?
O9 Gd1 O11 126.06(9) . . ?
N1 Gd1 O11 108.73(10) . . ?
O4 Gd1 O5 91.68(10) . . ?
O10 Gd1 O5 86.26(9) 3_667 . ?
O12 Gd1 O5 144.53(9) 3_767 . ?
O9 Gd1 O5 71.23(9) . . ?
N1 Gd1 O5 62.80(9) . . ?
O11 Gd1 O5 143.91(9) . . ?
O4 Gd1 O3 66.52(9) . . ?
O10 Gd1 O3 154.76(9) 3_667 . ?
O12 Gd1 O3 131.13(9) 3_767 . ?
O9 Gd1 O3 120.78(10) . . ?
N1 Gd1 O3 74.80(10) . . ?
O11 Gd1 O3 68.88(9) . . ?
O5 Gd1 O3 75.13(9) . . ?
O4 Gd1 N3 139.09(10) . . ?
O10 Gd1 N3 77.67(9) 3_667 . ?
O12 Gd1 N3 82.63(10) 3_767 . ?
O9 Gd1 N3 141.65(10) . . ?
N1 Gd1 N3 59.47(10) . . ?
O11 Gd1 N3 67.23(10) . . ?
O5 Gd1 N3 121.59(9) . . ?
O3 Gd1 N3 97.51(10) . . ?
O7 Gd2 O6 79.89(9) 4_666 4_666 ?
O7 Gd2 O8 145.71(10) 4_666 1_656 ?
O6 Gd2 O8 79.53(10) 4_666 1_656 ?
O7 Gd2 O15 85.57(11) 4_666 . ?
O6 Gd2 O15 72.37(11) 4_666 . ?
O8 Gd2 O15 113.58(10) 1_656 . ?
O7 Gd2 O1 140.26(10) 4_666 . ?
O6 Gd2 O1 123.47(10) 4_666 . ?
O8 Gd2 O1 73.93(10) 1_656 . ?
O15 Gd2 O1 74.17(11) . . ?
O7 Gd2 O13 102.90(10) 4_666 . ?
O6 Gd2 O13 142.47(11) 4_666 . ?
O8 Gd2 O13 78.17(11) 1_656 . ?
O15 Gd2 O13 144.78(11) . . ?
O1 Gd2 O13 78.07(10) . . ?
O7 Gd2 O2 75.84(9) 4_666 . ?
O6 Gd2 O2 140.76(10) 4_666 . ?
O8 Gd2 O2 134.88(10) 1_656 . ?
O15 Gd2 O2 75.42(11) . . ?
O1 Gd2 O2 66.23(9) . . ?
O13 Gd2 O2 73.78(11) . . ?
O7 Gd2 O14 74.28(11) 4_666 . ?
O6 Gd2 O14 72.27(10) 4_666 . ?
O8 Gd2 O14 73.47(10) 1_656 . ?
O15 Gd2 O14 141.72(11) . . ?
O1 Gd2 O14 139.72(11) . . ?
O13 Gd2 O14 72.64(11) . . ?
O2 Gd2 O14 127.90(10) . . ?
C3 N1 C2 107.2(3) . . ?
C3 N1 Gd1 130.0(3) . . ?
C2 N1 Gd1 122.8(2) . . ?
C3 N2 C1 108.8(3) . . ?
C3 N2 H2 155.0 . . ?
C1 N2 H2 95.6 . . ?
C8 N3 C4 116.7(4) . . ?
C8 N3 Gd1 125.0(3) . . ?
C4 N3 Gd1 117.2(3) . . ?
C13 O1 Gd2 121.1(3) . . ?
C14 O2 Gd2 118.6(2) . . ?
C14 O3 Gd1 113.9(2) . . ?
C13 O4 Gd1 115.3(2) . . ?
C10 O5 Gd1 125.4(2) . . ?
C10 O6 Gd2 148.1(3) . 4_465 ?
C9 O7 Gd2 147.6(3) . 4_465 ?
C9 O8 Gd2 124.4(3) . 1_454 ?
C11 O9 Gd1 118.8(2) . . ?
C11 O10 Gd1 118.6(2) . 3_667 ?
C12 O11 Gd1 117.3(2) . . ?
C12 O12 Gd1 118.1(3) . 3_767 ?
Gd2 O13 H13A 128(3) . . ?
Gd2 O13 H13B 117(3) . . ?
H13A O13 H13B 107.5(18) . . ?
Gd2 O14 H14A 114(3) . . ?
Gd2 O14 H14B 120(3) . . ?
H14A O14 H14B 107.7(18) . . ?
Gd2 O15 H15A 117(4) . . ?
Gd2 O15 H15B 116(3) . . ?
H15A O15 H15B 106.6(17) . . ?
H16A O16 H16B 107.7(18) . . ?
H17A O17 H17B 107.5(18) . . ?
N2 C1 C2 104.6(3) . . ?
N2 C1 C9 120.1(3) . . ?
C2 C1 C9 135.2(3) . . ?
N1 C2 C1 109.2(3) . . ?
N1 C2 C10 114.1(3) . . ?
C1 C2 C10 136.6(3) . . ?
N1 C3 N2 110.2(3) . . ?
N1 C3 C4 119.7(3) . . ?
N2 C3 C4 130.1(3) . . ?
N3 C4 C5 123.6(4) . . ?
N3 C4 C3 112.2(3) . . ?
C5 C4 C3 124.1(4) . . ?
C4 C5 C6 118.1(4) . . ?
C4 C5 H5 120.9 . . ?
C6 C5 H5 120.9 . . ?
C7 C6 C5 118.2(4) . . ?
C7 C6 H6 120.9 . . ?
C5 C6 H6 120.9 . . ?
C8 C7 C6 120.2(4) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
N3 C8 C7 123.2(4) . . ?
N3 C8 H8 118.4 . . ?
C7 C8 H8 118.4 . . ?
O8 C9 O7 125.0(4) . . ?
O8 C9 C1 114.9(3) . . ?
O7 C9 C1 120.0(3) . . ?
O6 C10 O5 123.4(4) . . ?
O6 C10 C2 122.9(3) . . ?
O5 C10 C2 113.7(3) . . ?
O9 C11 O10 126.2(4) . . ?
O9 C11 C11 116.2(4) . 3_667 ?
O10 C11 C11 117.6(4) . 3_667 ?
O11 C12 O12 126.7(4) . . ?
O11 C12 C12 117.1(4) . 3_767 ?
O12 C12 C12 116.2(4) . 3_767 ?
O1 C13 O4 126.2(4) . . ?
O1 C13 C14 117.2(4) . . ?
O4 C13 C14 116.6(4) . . ?
O3 C14 O2 126.8(4) . . ?
O3 C14 C13 117.2(3) . . ?
O2 C14 C13 116.0(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
C3 N2 C1 C2 -0.1(4) . . . . ?
C3 N2 C1 C9 -176.7(3) . . . . ?
C3 N1 C2 C1 0.3(4) . . . . ?
Gd1 N1 C2 C1 -177.6(2) . . . . ?
C3 N1 C2 C10 -178.7(3) . . . . ?
Gd1 N1 C2 C10 3.4(4) . . . . ?
N2 C1 C2 N1 -0.1(4) . . . . ?
C9 C1 C2 N1 175.7(4) . . . . ?
N2 C1 C2 C10 178.6(4) . . . . ?
C9 C1 C2 C10 -5.6(8) . . . . ?
C2 N1 C3 N2 -0.4(4) . . . . ?
Gd1 N1 C3 N2 177.3(2) . . . . ?
C2 N1 C3 C4 -178.9(3) . . . . ?
Gd1 N1 C3 C4 -1.2(5) . . . . ?
C1 N2 C3 N1 0.3(5) . . . . ?
C1 N2 C3 C4 178.7(4) . . . . ?
C8 N3 C4 C5 0.9(6) . . . . ?
Gd1 N3 C4 C5 -167.8(3) . . . . ?
C8 N3 C4 C3 -178.5(4) . . . . ?
Gd1 N3 C4 C3 12.8(4) . . . . ?
N1 C3 C4 N3 -8.7(5) . . . . ?
N2 C3 C4 N3 173.1(4) . . . . ?
N1 C3 C4 C5 171.9(4) . . . . ?
N2 C3 C4 C5 -6.4(7) . . . . ?
N3 C4 C5 C6 -0.6(7) . . . . ?
C3 C4 C5 C6 178.7(4) . . . . ?
C4 C5 C6 C7 -0.5(7) . . . . ?
C5 C6 C7 C8 1.3(8) . . . . ?
C4 N3 C8 C7 -0.1(7) . . . . ?
Gd1 N3 C8 C7 167.7(4) . . . . ?
C6 C7 C8 N3 -1.1(8) . . . . ?
Gd2 O8 C9 O7 -6.3(6) 1_454 . . . ?
Gd2 O8 C9 C1 173.1(2) 1_454 . . . ?
Gd2 O7 C9 O8 135.9(4) 4_465 . . . ?
Gd2 O7 C9 C1 -43.5(7) 4_465 . . . ?
N2 C1 C9 O8 7.7(5) . . . . ?
C2 C1 C9 O8 -167.6(4) . . . . ?
N2 C1 C9 O7 -172.9(3) . . . . ?
C2 C1 C9 O7 11.9(7) . . . . ?
Gd2 O6 C10 O5 -169.5(3) 4_465 . . . ?
Gd2 O6 C10 C2 12.3(7) 4_465 . . . ?
Gd1 O5 C10 O6 169.5(3) . . . . ?
Gd1 O5 C10 C2 -12.1(5) . . . . ?
N1 C2 C10 O6 -176.3(4) . . . . ?
C1 C2 C10 O6 5.0(7) . . . . ?
N1 C2 C10 O5 5.3(5) . . . . ?
C1 C2 C10 O5 -173.4(4) . . . . ?
Gd1 O9 C11 O10 -168.9(3) . . . . ?
Gd1 O9 C11 C11 10.9(5) . . . 3_667 ?
Gd1 O10 C11 O9 -169.0(3) 3_667 . . . ?
Gd1 O10 C11 C11 11.2(5) 3_667 . . 3_667 ?
Gd1 O11 C12 O12 162.8(3) . . . . ?
Gd1 O11 C12 C12 -17.2(6) . . . 3_767 ?
Gd1 O12 C12 O11 162.5(3) 3_767 . . . ?
Gd1 O12 C12 C12 -17.5(6) 3_767 . . 3_767 ?
Gd2 O1 C13 O4 179.4(3) . . . . ?
Gd2 O1 C13 C14 -0.7(5) . . . . ?
Gd1 O4 C13 O1 148.7(4) . . . . ?
Gd1 O4 C13 C14 -31.2(4) . . . . ?
Gd1 O3 C14 O2 -161.7(3) . . . . ?
Gd1 O3 C14 C13 16.7(4) . . . . ?
Gd2 O2 C14 O3 167.8(3) . . . . ?
Gd2 O2 C14 C13 -10.7(5) . . . . ?
O1 C13 C14 O3 -170.9(4) . . . . ?
O4 C13 C14 O3 9.1(6) . . . . ?
O1 C13 C14 O2 7.8(6) . . . . ?
O4 C13 C14 O2 -172.3(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
O17 H17A O16 0.818(10) 2.25(5) 2.865(9) 132(6) 1_554
O16 H16A O4 0.817(10) 2.33(9) 2.864(7) 123(9) 4_565
O15 H15B O2 0.819(10) 1.934(15) 2.741(4) 168(4) 4_566
O15 H15A O17 0.822(10) 1.99(2) 2.778(6) 160(4) 1_556
O14 H14B O5 0.820(10) 1.967(18) 2.761(4) 163(5) 1_655
O14 H14A O16 0.816(10) 2.125(16) 2.931(8) 169(4) 4_666
O13 H13B O5 0.816(10) 2.043(15) 2.833(4) 163(4) 1_655
O13 H13A O12 0.820(10) 2.006(12) 2.823(4) 174(5) .
N2 H2 O10 0.86 2.38 2.947(4) 123.4 1_554
N2 H2 O8 0.86 2.11 2.712(4) 126.2 .

_refine_diff_density_max         0.682
_refine_diff_density_min         -0.735
_refine_diff_density_rms         0.123

####################################################################### 
# 
# 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_Z1-La-zb162-2R1
_database_code_depnum_ccdc_archive 'CCDC 1506097'
_audit_update_record             
;
2017-02-28 deposited with the CCDC.
2017-03-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H7 La N3 O7'
_chemical_formula_weight         432.11

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
La La -0.2871 2.4523 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   7.1614(8)
_cell_length_b                   19.471(2)
_cell_length_c                   8.7123(9)
_cell_angle_alpha                90
_cell_angle_beta                 92.426(2)
_cell_angle_gamma                90
_cell_volume                     1213.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    6430
_cell_measurement_theta_min      3.03
_cell_measurement_theta_max      28.32

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.365
_exptl_crystal_F_000             828
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    3.565
_shelx_estimated_absorpt_T_min   0.368
_shelx_estimated_absorpt_T_max   0.469
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3684
_exptl_absorpt_correction_T_max  0.4694
_exptl_absorpt_process_details   '(HKL SCALEPACK; Otwinowski & Minor, 1997)'

_exptl_special_details           ?

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8483
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.033
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             2370
_reflns_number_gt                2080
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2 (Bruker, 2000)'
_computing_cell_refinement       'Bruker SAINT (Bruker, 2000)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     'w=1/[σ²(Fo²)] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2370
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0261
_refine_ls_wR_factor_ref         0.0497
_refine_ls_wR_factor_gt          0.0487
_refine_ls_goodness_of_fit_ref   1.670
_refine_ls_restrained_S_all      1.670
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
La1 La 0.30956(3) 0.14786(2) 0.89845(2) 0.01501(7) Uani 1 1 d . . . . .
O1 O 0.5249(4) 0.17233(14) 0.1215(3) 0.0269(7) Uani 1 1 d . . . . .
O2 O 0.6263(4) 0.26090(15) 0.2624(3) 0.0378(8) Uani 1 1 d . . . . .
O3 O 0.6394(4) 0.29091(15) 0.5921(3) 0.0369(8) Uani 1 1 d . . . . .
O4 O 0.5370(4) 0.23082(14) 0.7862(3) 0.0331(8) Uani 1 1 d . . . . .
O5 O 0.4115(3) -0.06391(13) 1.1161(3) 0.0220(6) Uani 1 1 d . . . . .
O6 O 0.3041(4) 0.04125(12) 1.0715(3) 0.0193(6) Uani 1 1 d . . . . .
O7 O -0.0546(5) 0.12068(18) 0.8859(5) 0.0578(11) Uani 1 1 d . . . . .
N1 N 0.2088(5) 0.02256(17) 0.7094(4) 0.0254(8) Uani 1 1 d . . . . .
N2 N 0.3930(4) 0.13332(15) 0.6161(4) 0.0177(7) Uani 1 1 d . . . . .
N3 N 0.3888(4) 0.10766(15) 0.3729(4) 0.0195(7) Uani 1 1 d . . . . .
H3A H 0.371900 0.086694 0.286021 0.023 Uiso 1 1 d R U . . .
C1 C 0.1285(6) -0.0344(2) 0.7612(5) 0.0320(11) Uani 1 1 d . . . . .
H1 H 0.095535 -0.035472 0.863314 0.038 Uiso 1 1 calc R U . . .
C2 C 0.0918(6) -0.0918(2) 0.6721(5) 0.0328(11) Uani 1 1 d . . . . .
H2 H 0.034918 -0.130192 0.713153 0.039 Uiso 1 1 calc R U . . .
C3 C 0.1414(6) -0.0911(2) 0.5198(6) 0.0323(11) Uani 1 1 d . . . . .
H3 H 0.118856 -0.129099 0.457089 0.039 Uiso 1 1 calc R U . . .
C4 C 0.2252(5) -0.03272(19) 0.4626(5) 0.0235(10) Uani 1 1 d . . . . .
H4 H 0.260491 -0.030767 0.361224 0.028 Uiso 1 1 calc R U . . .
C5 C 0.2546(5) 0.02218(19) 0.5600(5) 0.0189(8) Uani 1 1 d . . . . .
C6 C 0.3421(5) 0.08683(19) 0.5132(4) 0.0183(8) Uani 1 1 d . . . . .
C7 C 0.4775(5) 0.17048(18) 0.3864(5) 0.0175(8) Uani 1 1 d . . . . .
C8 C 0.4794(5) 0.18510(18) 0.5410(4) 0.0176(8) Uani 1 1 d . . . . .
C9 C 0.5479(5) 0.2043(2) 0.2455(5) 0.0218(9) Uani 1 1 d . . . . .
C10 C 0.5579(6) 0.2401(2) 0.6455(5) 0.0226(9) Uani 1 1 d . . . . .
C11 C 0.4184(5) -0.00639(19) 1.0541(4) 0.0156(8) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
La1 O3 2.435(3) 4_566 ?
La1 O1 2.476(3) 1_556 ?
La1 O2 2.480(3) 4_566 ?
La1 O4 2.521(3) . ?
La1 O6 2.567(2) . ?
La1 N2 2.572(3) . ?
La1 O5 2.588(3) 3_657 ?
La1 O7 2.659(3) . ?
La1 N1 3.014(3) . ?
O1 C9 1.251(4) . ?
O2 C9 1.243(4) . ?
O3 C10 1.249(5) . ?
O4 C10 1.254(5) . ?
O5 C11 1.245(4) . ?
O6 C11 1.251(4) . ?
N1 C1 1.337(5) . ?
N1 C5 1.356(5) . ?
N2 C6 1.314(4) . ?
N2 C8 1.364(5) . ?
N3 C6 1.344(5) . ?
N3 C7 1.381(4) . ?
N3 H3A 0.8639 . ?
C1 C2 1.379(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.388(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.387(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.375(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.471(5) . ?
C7 C8 1.376(5) . ?
C7 C9 1.499(5) . ?
C8 C10 1.499(5) . ?
C11 C11 1.552(7) 3_657 ?

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 La1 O1 71.03(10) 4_566 1_556 ?
O3 La1 O2 73.15(9) 4_566 4_566 ?
O1 La1 O2 122.45(10) 1_556 4_566 ?
O3 La1 O4 107.80(11) 4_566 . ?
O1 La1 O4 77.87(9) 1_556 . ?
O2 La1 O4 72.13(11) 4_566 . ?
O3 La1 O6 88.19(9) 4_566 . ?
O1 La1 O6 73.67(8) 1_556 . ?
O2 La1 O6 147.04(10) 4_566 . ?
O4 La1 O6 140.55(9) . . ?
O3 La1 N2 149.35(9) 4_566 . ?
O1 La1 N2 127.59(10) 1_556 . ?
O2 La1 N2 76.20(9) 4_566 . ?
O4 La1 N2 61.27(9) . . ?
O6 La1 N2 118.87(9) . . ?
O3 La1 O5 138.86(9) 4_566 3_657 ?
O1 La1 O5 72.76(9) 1_556 3_657 ?
O2 La1 O5 145.37(9) 4_566 3_657 ?
O4 La1 O5 82.70(9) . 3_657 ?
O6 La1 O5 63.19(8) . 3_657 ?
N2 La1 O5 70.89(9) . 3_657 ?
O3 La1 O7 66.86(12) 4_566 . ?
O1 La1 O7 130.37(11) 1_556 . ?
O2 La1 O7 67.96(11) 4_566 . ?
O4 La1 O7 139.51(11) . . ?
O6 La1 O7 79.86(10) . . ?
N2 La1 O7 101.89(11) . . ?
O5 La1 O7 129.05(9) 3_657 . ?
O3 La1 N1 131.29(10) 4_566 . ?
O1 La1 N1 135.36(9) 1_556 . ?
O2 La1 N1 102.07(9) 4_566 . ?
O4 La1 N1 116.77(9) . . ?
O6 La1 N1 69.95(9) . . ?
N2 La1 N1 56.50(9) . . ?
O5 La1 N1 68.26(8) 3_657 . ?
O7 La1 N1 66.72(10) . . ?
C9 O1 La1 145.9(3) . 1_554 ?
C9 O2 La1 156.8(3) . 4_665 ?
C10 O3 La1 154.4(3) . 4_665 ?
C10 O4 La1 125.2(2) . . ?
C11 O5 La1 120.1(2) . 3_657 ?
C11 O6 La1 120.2(2) . . ?
C1 N1 C5 116.4(4) . . ?
C1 N1 La1 125.7(3) . . ?
C5 N1 La1 117.8(2) . . ?
C6 N2 C8 107.5(3) . . ?
C6 N2 La1 131.2(3) . . ?
C8 N2 La1 120.4(2) . . ?
C6 N3 C7 108.7(3) . . ?
C6 N3 H3A 128.6 . . ?
C7 N3 H3A 122.7 . . ?
N1 C1 C2 123.8(4) . . ?
N1 C1 H1 118.1 . . ?
C2 C1 H1 118.1 . . ?
C1 C2 C3 118.7(4) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C4 C3 C2 118.9(4) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C5 C4 C3 118.2(4) . . ?
C5 C4 H4 120.9 . . ?
C3 C4 H4 120.9 . . ?
N1 C5 C4 124.0(4) . . ?
N1 C5 C6 112.6(3) . . ?
C4 C5 C6 123.4(4) . . ?
N2 C6 N3 109.9(3) . . ?
N2 C6 C5 120.6(4) . . ?
N3 C6 C5 129.5(3) . . ?
C8 C7 N3 104.6(3) . . ?
C8 C7 C9 136.1(3) . . ?
N3 C7 C9 119.2(3) . . ?
N2 C8 C7 109.3(3) . . ?
N2 C8 C10 113.7(3) . . ?
C7 C8 C10 136.9(4) . . ?
O2 C9 O1 125.9(4) . . ?
O2 C9 C7 117.3(3) . . ?
O1 C9 C7 116.9(3) . . ?
O3 C10 O4 123.7(4) . . ?
O3 C10 C8 120.6(4) . . ?
O4 C10 C8 115.7(3) . . ?
O5 C11 O6 125.2(4) . . ?
O5 C11 C11 116.9(4) . 3_657 ?
O6 C11 C11 117.9(4) . 3_657 ?

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
C5 N1 C1 C2 0.1(6) . . . . ?
La1 N1 C1 C2 -177.2(3) . . . . ?
N1 C1 C2 C3 0.4(6) . . . . ?
C1 C2 C3 C4 -0.3(6) . . . . ?
C2 C3 C4 C5 -0.3(6) . . . . ?
C1 N1 C5 C4 -0.7(6) . . . . ?
La1 N1 C5 C4 176.8(3) . . . . ?
C1 N1 C5 C6 -180.0(3) . . . . ?
La1 N1 C5 C6 -2.4(4) . . . . ?
C3 C4 C5 N1 0.8(6) . . . . ?
C3 C4 C5 C6 180.0(4) . . . . ?
C8 N2 C6 N3 -1.5(4) . . . . ?
La1 N2 C6 N3 167.3(2) . . . . ?
C8 N2 C6 C5 176.3(3) . . . . ?
La1 N2 C6 C5 -14.9(5) . . . . ?
C7 N3 C6 N2 1.1(4) . . . . ?
C7 N3 C6 C5 -176.5(4) . . . . ?
N1 C5 C6 N2 9.8(5) . . . . ?
C4 C5 C6 N2 -169.4(4) . . . . ?
N1 C5 C6 N3 -172.8(4) . . . . ?
C4 C5 C6 N3 7.9(6) . . . . ?
C6 N3 C7 C8 -0.2(4) . . . . ?
C6 N3 C7 C9 178.6(3) . . . . ?
C6 N2 C8 C7 1.4(4) . . . . ?
La1 N2 C8 C7 -168.8(2) . . . . ?
C6 N2 C8 C10 -175.9(3) . . . . ?
La1 N2 C8 C10 13.8(4) . . . . ?
N3 C7 C8 N2 -0.7(4) . . . . ?
C9 C7 C8 N2 -179.3(4) . . . . ?
N3 C7 C8 C10 175.7(4) . . . . ?
C9 C7 C8 C10 -2.9(8) . . . . ?
La1 O2 C9 O1 -150.5(5) 4_665 . . . ?
La1 O2 C9 C7 28.2(10) 4_665 . . . ?
La1 O1 C9 O2 -95.3(6) 1_554 . . . ?
La1 O1 C9 C7 85.9(5) 1_554 . . . ?
C8 C7 C9 O2 -1.9(7) . . . . ?
N3 C7 C9 O2 179.8(4) . . . . ?
C8 C7 C9 O1 177.0(4) . . . . ?
N3 C7 C9 O1 -1.4(5) . . . . ?
La1 O3 C10 O4 157.1(5) 4_665 . . . ?
La1 O3 C10 C8 -22.3(9) 4_665 . . . ?
La1 O4 C10 O3 163.7(3) . . . . ?
La1 O4 C10 C8 -16.9(5) . . . . ?
N2 C8 C10 O3 -179.4(4) . . . . ?
C7 C8 C10 O3 4.3(8) . . . . ?
N2 C8 C10 O4 1.2(5) . . . . ?
C7 C8 C10 O4 -175.1(4) . . . . ?
La1 O5 C11 O6 -169.7(3) 3_657 . . . ?
La1 O5 C11 C11 10.7(5) 3_657 . . 3_657 ?
La1 O6 C11 O5 -169.3(3) . . . . ?
La1 O6 C11 C11 10.2(5) . . . 3_657 ?

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
N3 H3A O6 0.86 2.11 2.966(4) 174.0 1_554

_refine_diff_density_max         1.551
_refine_diff_density_min         -0.766
_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_Z3-Pr-zb39-14R1
_database_code_depnum_ccdc_archive 'CCDC 1506099'
_audit_update_record             
;
2017-02-28 deposited with the CCDC.
2017-03-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H15 N3 O17 Pr2'
_chemical_formula_weight         779.11

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pr Pr -0.1570 2.9030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   9.6120(19)
_cell_length_b                   22.868(5)
_cell_length_c                   10.159(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.07(3)
_cell_angle_gamma                90
_cell_volume                     2191.5(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5856
_cell_measurement_theta_min      1.80
_cell_measurement_theta_max      29.55

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.361
_exptl_crystal_F_000             1496
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    4.604
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3459
_exptl_absorpt_correction_T_max  0.4461
_exptl_absorpt_process_details   '(HKL SCALEPACK; Otwinowski & Minor, 1997)'

_exptl_special_details           ?

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.720
_diffrn_radiation_type           synchrotron
_diffrn_source                   'synchrotron, 3W1A at BSRF'
_diffrn_measurement_device_type  mar165
_diffrn_measurement_method       'oscillation mode'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4495
_diffrn_reflns_av_unetI/netI     0.0155
_diffrn_reflns_av_R_equivalents  0.0566
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_theta_min         1.804
_diffrn_reflns_theta_max         26.995
_diffrn_reflns_theta_full        25.595
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             4495
_reflns_number_gt                4489
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0255P)²+7.3536P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4495
_refine_ls_number_parameters     331
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0206
_refine_ls_R_factor_gt           0.0205
_refine_ls_wR_factor_ref         0.0554
_refine_ls_wR_factor_gt          0.0554
_refine_ls_goodness_of_fit_ref   1.150
_refine_ls_restrained_S_all      1.148
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Pr1 Pr 1.25589(2) 0.27799(2) 1.03749(2) 0.00382(6) Uani 1 1 d . . . . .
Pr2 Pr 0.72041(2) 0.43549(2) 0.85034(2) 0.00272(6) Uani 1 1 d . . . . .
N1 N 0.5972(3) 0.41592(10) 0.6139(2) 0.0054(5) Uani 1 1 d . . . . .
N2 N 0.5336(3) 0.41630(11) 0.3942(2) 0.0059(5) Uani 1 1 d . . . . .
H2 H 0.528707 0.426331 0.309799 0.007 Uiso 1 1 calc R U . . .
N3 N 0.7713(3) 0.50727(12) 0.6359(3) 0.0099(5) Uani 1 1 d . . . . .
O1 O 1.0688(2) 0.34065(9) 1.0988(2) 0.0105(4) Uani 1 1 d . . . . .
O2 O 1.0391(2) 0.29129(9) 0.8552(2) 0.0085(4) Uani 1 1 d . . . . .
O3 O 0.8503(2) 0.37878(10) 1.0427(2) 0.0108(4) Uani 1 1 d . . . . .
O4 O 0.8390(2) 0.34303(9) 0.7862(2) 0.0083(4) Uani 1 1 d . . . . .
O5 O 1.2834(2) 0.37420(9) 0.9263(2) 0.0089(4) Uani 1 1 d . . . . .
H5A H 1.233654 0.402297 0.933534 0.013 Uiso 1 1 d R U . . .
H5B H 1.358684 0.376290 0.899603 0.013 Uiso 1 1 d R U . . .
O6 O 1.5171(2) 0.28399(10) 1.0156(2) 0.0123(4) Uani 1 1 d . . . . .
H6A H 1.568339 0.297919 1.091886 0.018 Uiso 1 1 d R U . . .
H6B H 1.525403 0.307848 0.948142 0.018 Uiso 1 1 d R U . . .
O7 O 1.0712(2) 0.21223(10) 1.0958(2) 0.0104(4) Uani 1 1 d . . . . .
H7A H 0.996171 0.215240 1.057151 0.016 Uiso 1 1 d R U . . .
H7B H 1.084036 0.207764 1.179146 0.016 Uiso 1 1 d R U . . .
O8 O 0.5964(2) 0.43569(9) 1.0441(2) 0.0084(4) Uani 1 1 d . . . . .
O9 O 0.4711(2) 0.48968(9) 1.1642(2) 0.0070(4) Uani 1 1 d . . . . .
O10 O 0.3794(2) 0.29746(9) 0.6809(2) 0.0086(4) Uani 1 1 d . . . . .
O11 O 0.5221(2) 0.36037(9) 0.8091(2) 0.0067(4) Uani 1 1 d . . . . .
O12 O 0.2832(2) 0.29676(9) 0.3799(2) 0.0085(4) Uani 1 1 d . U . . .
O13 O 0.3756(2) 0.34096(9) 0.2205(2) 0.0098(4) Uani 1 1 d . U . . .
O14 O 1.1781(2) 0.48027(9) 1.0062(2) 0.0095(4) Uani 1 1 d . . . . .
O15 O 0.9804(2) 0.45148(9) 0.8648(2) 0.0082(4) Uani 1 1 d . . . . .
O16 O 0.7703(3) 0.21202(12) 0.0202(3) 0.0213(5) Uani 1 1 d D . . . .
H16B H 0.781(5) 0.2449(7) 0.052(4) 0.032 Uiso 1 1 d D U . . .
H16A H 0.790(5) 0.1888(13) 0.083(3) 0.032 Uiso 1 1 d D U . . .
O17 O 0.7192(3) 0.16579(17) 0.7581(3) 0.0440(9) Uani 1 1 d . . . . .
H17B H 0.788269 0.148709 0.737214 0.066 Uiso 1 1 d R U . . .
H17A H 0.709740 0.149575 0.825792 0.066 Uiso 1 1 d R U . . .
C1 C 0.4573(3) 0.37187(12) 0.4402(3) 0.0047(5) Uani 1 1 d . . . . .
C2 C 0.4982(3) 0.37277(12) 0.5785(3) 0.0053(5) Uani 1 1 d . . . . .
C3 C 0.6170(3) 0.44153(12) 0.5014(3) 0.0049(5) Uani 1 1 d . . . . .
C4 C 0.7194(3) 0.49003(13) 0.5077(3) 0.0071(5) Uani 1 1 d . . . . .
C5 C 0.7595(3) 0.51474(14) 0.3964(3) 0.0124(6) Uani 1 1 d . . . . .
H5 H 0.722718 0.500567 0.308694 0.015 Uiso 1 1 calc R U . . .
C6 C 0.8562(4) 0.56138(15) 0.4168(4) 0.0170(7) Uani 1 1 d . . . . .
H6 H 0.885921 0.579643 0.342901 0.020 Uiso 1 1 calc R U . . .
C7 C 0.9077(3) 0.58040(15) 0.5470(4) 0.0161(7) Uani 1 1 d . . . . .
H7 H 0.972320 0.612193 0.563339 0.019 Uiso 1 1 calc R U . . .
C8 C 0.8632(3) 0.55219(14) 0.6531(3) 0.0123(6) Uani 1 1 d . . . . .
H8 H 0.899493 0.565296 0.741810 0.015 Uiso 1 1 calc R U . . .
C9 C 0.5203(3) 0.47822(12) 1.0595(3) 0.0046(5) Uani 1 1 d . . . . .
C10 C 1.0449(3) 0.48019(12) 0.9617(3) 0.0060(5) Uani 1 1 d . . . . .
C11 C 0.4618(3) 0.34007(12) 0.6946(3) 0.0043(5) Uani 1 1 d . . . . .
C12 C 0.3646(3) 0.33369(12) 0.3404(3) 0.0058(5) Uani 1 1 d . U . . .
C13 C 0.9551(3) 0.35014(12) 1.0188(3) 0.0074(5) Uani 1 1 d . . . . .
C14 C 0.9419(3) 0.32556(12) 0.8732(3) 0.0072(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Pr1 O12 2.390(2) 4_666 ?
Pr1 O10 2.418(2) 4_666 ?
Pr1 O13 2.456(2) 1_656 ?
Pr1 O1 2.471(2) . ?
Pr1 O7 2.483(2) . ?
Pr1 O5 2.510(2) . ?
Pr1 O2 2.526(2) . ?
Pr1 O6 2.566(2) . ?
Pr2 O3 2.474(2) . ?
Pr2 O8 2.489(2) . ?
Pr2 O9 2.497(2) 3_667 ?
Pr2 O14 2.498(2) 3_767 ?
Pr2 O15 2.502(2) . ?
Pr2 N1 2.506(3) . ?
Pr2 O11 2.540(2) . ?
Pr2 O4 2.545(2) . ?
Pr2 N3 2.844(3) . ?
N1 C3 1.330(4) . ?
N1 C2 1.371(4) . ?
N2 C3 1.351(4) . ?
N2 C1 1.386(4) . ?
N2 H2 0.8800 . ?
N3 C8 1.344(4) . ?
N3 C4 1.360(4) . ?
O1 C13 1.249(4) . ?
O2 C14 1.260(4) . ?
O3 C13 1.263(4) . ?
O4 C14 1.258(4) . ?
O5 H5A 0.8128 . ?
O5 H5B 0.8213 . ?
O6 H6A 0.8933 . ?
O6 H6B 0.8916 . ?
O7 H7A 0.7547 . ?
O7 H7B 0.8386 . ?
O8 C9 1.245(4) . ?
O9 C9 1.272(4) . ?
O10 C11 1.247(4) . ?
O11 C11 1.283(4) . ?
O12 C12 1.268(4) . ?
O13 C12 1.253(4) . ?
O14 C10 1.274(4) . ?
O15 C10 1.245(4) . ?
O16 H16B 0.819(10) . ?
O16 H16A 0.823(10) . ?
O17 H17B 0.8323 . ?
O17 H17A 0.8012 . ?
C1 C2 1.385(4) . ?
C1 C12 1.496(4) . ?
C2 C11 1.493(4) . ?
C3 C4 1.476(4) . ?
C4 C5 1.384(4) . ?
C5 C6 1.403(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.390(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.392(5) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C9 1.557(5) 3_667 ?
C10 C10 1.559(5) 3_767 ?
C13 C14 1.564(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O12 Pr1 O10 77.82(7) 4_666 4_666 ?
O12 Pr1 O13 146.14(7) 4_666 1_656 ?
O10 Pr1 O13 81.82(7) 4_666 1_656 ?
O12 Pr1 O1 139.66(7) 4_666 . ?
O10 Pr1 O1 123.98(7) 4_666 . ?
O13 Pr1 O1 74.17(8) 1_656 . ?
O12 Pr1 O7 84.38(8) 4_666 . ?
O10 Pr1 O7 73.44(8) 4_666 . ?
O13 Pr1 O7 115.28(7) 1_656 . ?
O1 Pr1 O7 72.71(8) . . ?
O12 Pr1 O5 106.90(7) 4_666 . ?
O10 Pr1 O5 144.56(7) 4_666 . ?
O13 Pr1 O5 75.66(7) 1_656 . ?
O1 Pr1 O5 75.51(7) . . ?
O7 Pr1 O5 141.25(7) . . ?
O12 Pr1 O2 77.08(7) 4_666 . ?
O10 Pr1 O2 140.19(7) 4_666 . ?
O13 Pr1 O2 133.22(7) 1_656 . ?
O1 Pr1 O2 64.98(7) . . ?
O7 Pr1 O2 73.79(7) . . ?
O5 Pr1 O2 73.01(7) . . ?
O12 Pr1 O6 75.24(8) 4_666 . ?
O10 Pr1 O6 73.45(7) 4_666 . ?
O13 Pr1 O6 73.16(8) 1_656 . ?
O1 Pr1 O6 139.67(7) . . ?
O7 Pr1 O6 144.01(7) . . ?
O5 Pr1 O6 74.02(7) . . ?
O2 Pr1 O6 127.80(7) . . ?
O3 Pr2 O8 67.80(7) . . ?
O3 Pr2 O9 131.34(7) . 3_667 ?
O8 Pr2 O9 65.55(7) . 3_667 ?
O3 Pr2 O14 82.08(8) . 3_767 ?
O8 Pr2 O14 74.32(7) . 3_767 ?
O9 Pr2 O14 72.95(7) 3_667 3_767 ?
O3 Pr2 O15 71.53(8) . . ?
O8 Pr2 O15 125.30(8) . . ?
O9 Pr2 O15 128.31(7) 3_667 . ?
O14 Pr2 O15 65.13(7) 3_767 . ?
O3 Pr2 N1 137.51(8) . . ?
O8 Pr2 N1 123.27(8) . . ?
O9 Pr2 N1 81.86(8) 3_667 . ?
O14 Pr2 N1 139.16(8) 3_767 . ?
O15 Pr2 N1 111.41(8) . . ?
O3 Pr2 O11 91.42(8) . . ?
O8 Pr2 O11 70.94(7) . . ?
O9 Pr2 O11 86.12(7) 3_667 . ?
O14 Pr2 O11 144.50(7) 3_767 . ?
O15 Pr2 O11 144.88(7) . . ?
N1 Pr2 O11 61.31(7) . . ?
O3 Pr2 O4 65.41(7) . . ?
O8 Pr2 O4 120.65(7) . . ?
O9 Pr2 O4 156.27(7) 3_667 . ?
O14 Pr2 O4 130.24(7) 3_767 . ?
O15 Pr2 O4 69.21(7) . . ?
N1 Pr2 O4 76.04(7) . . ?
O11 Pr2 O4 75.81(7) . . ?
O3 Pr2 N3 140.56(7) . . ?
O8 Pr2 N3 141.59(7) . . ?
O9 Pr2 N3 78.02(7) 3_667 . ?
O14 Pr2 N3 84.06(8) 3_767 . ?
O15 Pr2 N3 69.13(8) . . ?
N1 Pr2 N3 59.20(8) . . ?
O11 Pr2 N3 119.88(7) . . ?
O4 Pr2 N3 97.59(7) . . ?
C3 N1 C2 107.4(2) . . ?
C3 N1 Pr2 128.76(19) . . ?
C2 N1 Pr2 123.80(19) . . ?
C3 N2 C1 108.2(2) . . ?
C3 N2 H2 125.9 . . ?
C1 N2 H2 125.9 . . ?
C8 N3 C4 117.2(3) . . ?
C8 N3 Pr2 123.1(2) . . ?
C4 N3 Pr2 118.72(19) . . ?
C13 O1 Pr1 121.68(19) . . ?
C14 O2 Pr1 119.94(19) . . ?
C13 O3 Pr2 114.85(19) . . ?
C14 O4 Pr2 114.48(18) . . ?
Pr1 O5 H5A 122.5 . . ?
Pr1 O5 H5B 112.0 . . ?
H5A O5 H5B 123.7 . . ?
Pr1 O6 H6A 109.3 . . ?
Pr1 O6 H6B 109.5 . . ?
H6A O6 H6B 109.4 . . ?
Pr1 O7 H7A 118.4 . . ?
Pr1 O7 H7B 109.9 . . ?
H7A O7 H7B 118.5 . . ?
C9 O8 Pr2 118.88(18) . . ?
C9 O9 Pr2 118.70(18) . 3_667 ?
C11 O10 Pr1 148.5(2) . 4_465 ?
C11 O11 Pr2 126.01(18) . . ?
C12 O12 Pr1 147.37(19) . 4_465 ?
C12 O13 Pr1 122.90(19) . 1_454 ?
C10 O14 Pr2 117.49(18) . 3_767 ?
C10 O15 Pr2 117.62(18) . . ?
H16B O16 H16A 107.0(17) . . ?
H17B O17 H17A 103.3 . . ?
C2 C1 N2 105.4(2) . . ?
C2 C1 C12 135.4(3) . . ?
N2 C1 C12 119.0(2) . . ?
N1 C2 C1 108.9(2) . . ?
N1 C2 C11 114.2(2) . . ?
C1 C2 C11 136.9(3) . . ?
N1 C3 N2 110.1(2) . . ?
N1 C3 C4 119.8(3) . . ?
N2 C3 C4 130.0(3) . . ?
N3 C4 C5 123.7(3) . . ?
N3 C4 C3 112.2(3) . . ?
C5 C4 C3 124.0(3) . . ?
C4 C5 C6 118.0(3) . . ?
C4 C5 H5 121.0 . . ?
C6 C5 H5 121.0 . . ?
C7 C6 C5 118.9(3) . . ?
C7 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C6 C7 C8 119.1(3) . . ?
C6 C7 H7 120.5 . . ?
C8 C7 H7 120.5 . . ?
N3 C8 C7 123.0(3) . . ?
N3 C8 H8 118.5 . . ?
C7 C8 H8 118.5 . . ?
O8 C9 O9 126.0(3) . . ?
O8 C9 C9 117.9(3) . 3_667 ?
O9 C9 C9 116.1(3) . 3_667 ?
O15 C10 O14 126.6(3) . . ?
O15 C10 C10 117.5(3) . 3_767 ?
O14 C10 C10 115.9(3) . 3_767 ?
O10 C11 O11 123.4(3) . . ?
O10 C11 C2 122.9(3) . . ?
O11 C11 C2 113.7(2) . . ?
O13 C12 O12 124.6(3) . . ?
O13 C12 C1 115.5(3) . . ?
O12 C12 C1 119.8(3) . . ?
O1 C13 O3 126.5(3) . . ?
O1 C13 C14 117.0(3) . . ?
O3 C13 C14 116.4(3) . . ?
O4 C14 O2 126.9(3) . . ?
O4 C14 C13 117.4(3) . . ?
O2 C14 C13 115.7(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N2 C1 C2 0.8(3) . . . . ?
C3 N2 C1 C12 -175.3(2) . . . . ?
C3 N1 C2 C1 0.5(3) . . . . ?
Pr2 N1 C2 C1 -176.79(18) . . . . ?
C3 N1 C2 C11 -179.1(2) . . . . ?
Pr2 N1 C2 C11 3.7(3) . . . . ?
N2 C1 C2 N1 -0.8(3) . . . . ?
C12 C1 C2 N1 174.3(3) . . . . ?
N2 C1 C2 C11 178.6(3) . . . . ?
C12 C1 C2 C11 -6.3(6) . . . . ?
C2 N1 C3 N2 0.0(3) . . . . ?
Pr2 N1 C3 N2 177.10(18) . . . . ?
C2 N1 C3 C4 -179.7(2) . . . . ?
Pr2 N1 C3 C4 -2.6(4) . . . . ?
C1 N2 C3 N1 -0.5(3) . . . . ?
C1 N2 C3 C4 179.2(3) . . . . ?
C8 N3 C4 C5 2.2(4) . . . . ?
Pr2 N3 C4 C5 -167.1(2) . . . . ?
C8 N3 C4 C3 -178.5(3) . . . . ?
Pr2 N3 C4 C3 12.2(3) . . . . ?
N1 C3 C4 N3 -7.2(4) . . . . ?
N2 C3 C4 N3 173.1(3) . . . . ?
N1 C3 C4 C5 172.1(3) . . . . ?
N2 C3 C4 C5 -7.6(5) . . . . ?
N3 C4 C5 C6 -1.9(5) . . . . ?
C3 C4 C5 C6 178.9(3) . . . . ?
C4 C5 C6 C7 0.3(5) . . . . ?
C5 C6 C7 C8 0.8(5) . . . . ?
C4 N3 C8 C7 -1.0(5) . . . . ?
Pr2 N3 C8 C7 167.8(2) . . . . ?
C6 C7 C8 N3 -0.5(5) . . . . ?
Pr2 O8 C9 O9 -166.7(2) . . . . ?
Pr2 O8 C9 C9 13.7(4) . . . 3_667 ?
Pr2 O9 C9 O8 -166.6(2) 3_667 . . . ?
Pr2 O9 C9 C9 13.1(4) 3_667 . . 3_667 ?
Pr2 O15 C10 O14 160.2(2) . . . . ?
Pr2 O15 C10 C10 -19.1(4) . . . 3_767 ?
Pr2 O14 C10 O15 160.7(2) 3_767 . . . ?
Pr2 O14 C10 C10 -20.0(4) 3_767 . . 3_767 ?
Pr1 O10 C11 O11 -164.1(2) 4_465 . . . ?
Pr1 O10 C11 C2 16.6(5) 4_465 . . . ?
Pr2 O11 C11 O10 169.5(2) . . . . ?
Pr2 O11 C11 C2 -11.2(3) . . . . ?
N1 C2 C11 O10 -176.2(3) . . . . ?
C1 C2 C11 O10 4.5(5) . . . . ?
N1 C2 C11 O11 4.5(3) . . . . ?
C1 C2 C11 O11 -174.8(3) . . . . ?
Pr1 O13 C12 O12 -5.9(4) 1_454 . . . ?
Pr1 O13 C12 C1 173.49(17) 1_454 . . . ?
Pr1 O12 C12 O13 133.8(3) 4_465 . . . ?
Pr1 O12 C12 C1 -45.5(5) 4_465 . . . ?
C2 C1 C12 O13 -166.9(3) . . . . ?
N2 C1 C12 O13 7.7(4) . . . . ?
C2 C1 C12 O12 12.5(5) . . . . ?
N2 C1 C12 O12 -172.9(3) . . . . ?
Pr1 O1 C13 O3 176.0(2) . . . . ?
Pr1 O1 C13 C14 -5.7(3) . . . . ?
Pr2 O3 C13 O1 145.4(3) . . . . ?
Pr2 O3 C13 C14 -32.9(3) . . . . ?
Pr2 O4 C14 O2 -160.6(2) . . . . ?
Pr2 O4 C14 C13 17.2(3) . . . . ?
Pr1 O2 C14 O4 168.9(2) . . . . ?
Pr1 O2 C14 C13 -8.9(3) . . . . ?
O1 C13 C14 O4 -168.3(3) . . . . ?
O3 C13 C14 O4 10.2(4) . . . . ?
O1 C13 C14 O2 9.7(4) . . . . ?
O3 C13 C14 O2 -171.7(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O9 0.88 2.07 2.845(3) 146.7 1_554
O5 H5A O14 0.81 2.04 2.808(3) 157.4 .
O5 H5A O15 0.81 2.65 3.361(3) 147.0 .
O5 H5B O11 0.82 2.00 2.798(3) 163.9 1_655
O6 H6A O17 0.89 2.17 3.054(5) 170.7 4_666
O6 H6B O11 0.89 1.85 2.737(3) 173.4 1_655
O7 H7A O16 0.75 2.13 2.846(4) 158.0 1_556
O7 H7B O2 0.84 1.92 2.713(3) 157.6 4_566
O16 H16B O6 0.819(10) 2.65(5) 2.931(4) 102(4) 1_454
O16 H16A O4 0.823(10) 2.157(19) 2.940(3) 159(4) 4_565
O17 H17B O3 0.83 2.26 2.912(4) 135.3 4_565
O17 H17A N2 0.80 2.46 3.092(5) 136.2 4_566
O17 H17A O16 0.80 2.42 2.818(4) 112.2 1_556

_refine_diff_density_max         0.896
_refine_diff_density_min         -1.520
_refine_diff_density_rms         0.124

####################################################################### 
# 
# 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_zlyzb66-14
_database_code_depnum_ccdc_archive 'CCDC 1506100'
_audit_update_record             
;
2017-01-20 deposited with the CCDC.
2017-03-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H15 N3 Nd2 O17'
_chemical_formula_weight         785.77

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Nd Nd -0.1330 3.1040 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   9.5940(19)
_cell_length_b                   22.789(5)
_cell_length_c                   10.146(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.32(3)
_cell_angle_gamma                90
_cell_volume                     2175.2(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    12007
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      26.00

_exptl_crystal_description       block
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.399
_exptl_crystal_F_000             1504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    4.946
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3684
_exptl_absorpt_correction_T_max  0.4694
_exptl_absorpt_process_details   '(HKL SCALEPACK; Otwinowski & Minor, 1997)'

_exptl_special_details           ?

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.720
_diffrn_radiation_type           synchrotron
_diffrn_source                   'synchrotron, 3W1A at BSRF'
_diffrn_measurement_device_type  mar165
_diffrn_measurement_method       'oscillation mode'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7627
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.373
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_full        25.595
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measured_fraction_theta_full 0.954
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_Laue_measured_fraction_full 0.954
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_point_group_measured_fraction_full 0.954
_reflns_number_total             3922
_reflns_number_gt                3710
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0256P)²+2.8156P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3922
_refine_ls_number_parameters     325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0200
_refine_ls_R_factor_gt           0.0187
_refine_ls_wR_factor_ref         0.0486
_refine_ls_wR_factor_gt          0.0479
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Nd1 Nd 1.25464(2) 0.27797(2) 1.03910(2) 0.00604(6) Uani 1 1 d . . . . .
Nd2 Nd 0.71997(2) 0.43537(2) 0.85184(2) 0.00493(6) Uani 1 1 d . . . . .
N1 N 0.5976(2) 0.41577(10) 0.6156(2) 0.0078(5) Uani 1 1 d . . . . .
N2 N 0.5339(2) 0.41565(10) 0.3953(3) 0.0079(5) Uani 1 1 d . . . . .
H2 H 0.5198 0.4275 0.3134 0.012 Uiso 1 1 d R U . . .
N3 N 0.7720(2) 0.50723(11) 0.6384(3) 0.0121(5) Uani 1 1 d . . . . .
O1 O 1.0680(2) 0.34014(9) 1.1013(2) 0.0119(4) Uani 1 1 d . . . . .
O2 O 1.0383(2) 0.29070(9) 0.8567(2) 0.0102(4) Uani 1 1 d . . . . .
O3 O 0.8370(2) 0.34288(8) 0.7871(2) 0.0105(4) Uani 1 1 d . . . . .
O4 O 0.8495(2) 0.37893(9) 1.0437(2) 0.0120(4) Uani 1 1 d . . . . .
O5 O 0.5223(2) 0.36028(8) 0.8117(2) 0.0087(4) Uani 1 1 d . . . . .
O6 O 0.3788(2) 0.29698(8) 0.6833(2) 0.0105(4) Uani 1 1 d . . . . .
O7 O 0.2822(2) 0.29621(8) 0.3815(2) 0.0101(4) Uani 1 1 d . . . . .
O8 O 0.3740(2) 0.34038(9) 0.2216(2) 0.0117(4) Uani 1 1 d . . . . .
O9 O 0.5980(2) 0.43609(8) 1.0451(2) 0.0104(4) Uani 1 1 d . . . . .
O10 O 0.4709(2) 0.48992(9) 1.1642(2) 0.0092(4) Uani 1 1 d . . . . .
O11 O 0.9801(2) 0.45067(9) 0.8658(2) 0.0098(4) Uani 1 1 d . . . . .
O12 O 1.1782(2) 0.48015(8) 1.0066(2) 0.0114(4) Uani 1 1 d . . . . .
O13 O 1.2823(2) 0.37324(8) 0.9276(2) 0.0112(4) Uani 1 1 d . . . . .
H13A H 1.2485 0.4052 0.9412 0.017 Uiso 1 1 d R U . . .
H13B H 1.3499 0.3794 0.8911 0.017 Uiso 1 1 d R U . . .
O14 O 1.5153(2) 0.28405(9) 1.0186(2) 0.0143(5) Uani 1 1 d . . . . .
H14A H 1.5750 0.2916 1.0862 0.022 Uiso 1 1 d R U . . .
H14B H 1.5271 0.3072 0.9598 0.022 Uiso 1 1 d R U . . .
O15 O 1.0721(2) 0.21177(9) 1.0972(2) 0.0120(4) Uani 1 1 d . . . . .
H15A H 0.9897 0.2152 1.0568 0.018 Uiso 1 1 d R U . . .
H15B H 1.0705 0.2116 1.1777 0.018 Uiso 1 1 d R U . . .
O16 O 0.7172(3) 0.16764(16) 0.7562(3) 0.0522(9) Uani 1 1 d . . . . .
H16B H 0.7728 0.1542 0.7122 0.078 Uiso 1 1 d R U . . .
H16A H 0.7645 0.1845 0.8213 0.078 Uiso 1 1 d R U . . .
O17 O 0.7719(2) 0.21157(11) 0.0217(3) 0.0229(5) Uani 1 1 d . . . . .
H17B H 0.7026 0.2324 0.0234 0.034 Uiso 1 1 d R U . . .
H17A H 0.7919 0.1947 0.0943 0.034 Uiso 1 1 d R U . . .
C1 C 0.4571(3) 0.37123(12) 0.4420(3) 0.0076(6) Uani 1 1 d . . . . .
C2 C 0.4983(3) 0.37218(11) 0.5803(3) 0.0065(5) Uani 1 1 d . . . . .
C3 C 0.6175(3) 0.44125(12) 0.5037(3) 0.0071(6) Uani 1 1 d . . . . .
C4 C 0.7195(3) 0.48964(12) 0.5098(3) 0.0090(6) Uani 1 1 d . . . . .
C5 C 0.7607(3) 0.51467(14) 0.3981(3) 0.0165(7) Uani 1 1 d . . . . .
H5 H 0.7241 0.5005 0.3101 0.020 Uiso 1 1 calc R U . . .
C6 C 0.8575(4) 0.56132(14) 0.4192(4) 0.0203(7) Uani 1 1 d . . . . .
H6 H 0.8881 0.5795 0.3455 0.024 Uiso 1 1 calc R U . . .
C7 C 0.9077(3) 0.58043(13) 0.5490(4) 0.0188(7) Uani 1 1 d . . . . .
H7 H 0.9718 0.6126 0.5653 0.023 Uiso 1 1 calc R U . . .
C8 C 0.8641(3) 0.55237(13) 0.6558(3) 0.0157(7) Uani 1 1 d . . . . .
H8 H 0.9008 0.5656 0.7446 0.019 Uiso 1 1 calc R U . . .
C9 C 0.3632(3) 0.33302(11) 0.3418(3) 0.0071(6) Uani 1 1 d . . . . .
C10 C 0.4617(3) 0.33953(12) 0.6963(3) 0.0064(5) Uani 1 1 d . . . . .
C11 C 0.5202(3) 0.47836(11) 1.0605(3) 0.0069(6) Uani 1 1 d . . . . .
C12 C 1.0452(3) 0.47999(12) 0.9617(3) 0.0084(6) Uani 1 1 d . . . . .
C13 C 0.9542(3) 0.34982(12) 1.0204(3) 0.0097(6) Uani 1 1 d . . . . .
C14 C 0.9410(3) 0.32542(12) 0.8750(3) 0.0088(6) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Nd1 O7 2.377(2) 4_666 ?
Nd1 O6 2.407(2) 4_666 ?
Nd1 O8 2.436(2) 1_656 ?
Nd1 O1 2.461(2) . ?
Nd1 O15 2.469(2) . ?
Nd1 O13 2.486(2) . ?
Nd1 O2 2.512(2) . ?
Nd1 O14 2.554(2) . ?
Nd2 O4 2.457(2) . ?
Nd2 O9 2.473(2) . ?
Nd2 O10 2.4824(19) 3_667 ?
Nd2 O12 2.485(2) 3_767 ?
Nd2 N1 2.494(3) . ?
Nd2 O11 2.497(2) . ?
Nd2 O5 2.5275(19) . ?
Nd2 O3 2.5345(19) . ?
Nd2 N3 2.837(3) . ?
N1 C3 1.322(4) . ?
N1 C2 1.374(4) . ?
N2 C3 1.359(4) . ?
N2 C1 1.388(4) . ?
N2 H2 0.8594 . ?
N3 C8 1.345(4) . ?
N3 C4 1.363(4) . ?
O1 C13 1.250(4) . ?
O2 C14 1.265(3) . ?
O3 C14 1.265(4) . ?
O4 C13 1.265(4) . ?
O5 C10 1.290(3) . ?
O6 C10 1.245(3) . ?
O6 Nd1 2.407(2) 4_465 ?
O7 C9 1.262(3) . ?
O7 Nd1 2.377(2) 4_465 ?
O8 C9 1.255(4) . ?
O8 Nd1 2.435(2) 1_454 ?
O9 C11 1.247(3) . ?
O10 C11 1.263(4) . ?
O10 Nd2 2.4823(19) 3_667 ?
O11 C12 1.243(4) . ?
O12 C12 1.268(3) . ?
O12 Nd2 2.485(2) 3_767 ?
O13 H13A 0.8200 . ?
O13 H13B 0.8199 . ?
O14 H14A 0.8200 . ?
O14 H14B 0.8200 . ?
O15 H15A 0.8200 . ?
O15 H15B 0.8200 . ?
O16 H16B 0.8200 . ?
O16 H16A 0.8200 . ?
O17 H17B 0.8200 . ?
O17 H17A 0.8200 . ?
C1 C2 1.381(4) . ?
C1 C9 1.498(4) . ?
C2 C10 1.492(4) . ?
C3 C4 1.468(4) . ?
C4 C5 1.393(4) . ?
C5 C6 1.401(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.381(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.392(5) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C11 C11 1.563(5) 3_667 ?
C12 C12 1.566(6) 3_767 ?
C13 C14 1.558(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O7 Nd1 O6 78.29(7) 4_666 4_666 ?
O7 Nd1 O8 146.01(7) 4_666 1_656 ?
O6 Nd1 O8 81.34(7) 4_666 1_656 ?
O7 Nd1 O1 139.85(7) 4_666 . ?
O6 Nd1 O1 123.45(7) 4_666 . ?
O8 Nd1 O1 74.10(7) 1_656 . ?
O7 Nd1 O15 84.47(7) 4_666 . ?
O6 Nd1 O15 73.20(7) 4_666 . ?
O8 Nd1 O15 115.16(7) 1_656 . ?
O1 Nd1 O15 72.82(7) . . ?
O7 Nd1 O13 106.21(7) 4_666 . ?
O6 Nd1 O13 144.27(7) 4_666 . ?
O8 Nd1 O13 76.09(7) 1_656 . ?
O1 Nd1 O13 76.23(7) . . ?
O15 Nd1 O13 141.85(7) . . ?
O7 Nd1 O2 76.78(7) 4_666 . ?
O6 Nd1 O2 140.24(7) 4_666 . ?
O8 Nd1 O2 133.63(7) 1_656 . ?
O1 Nd1 O2 65.47(7) . . ?
O15 Nd1 O2 74.00(7) . . ?
O13 Nd1 O2 73.17(7) . . ?
O7 Nd1 O14 75.17(7) 4_666 . ?
O6 Nd1 O14 73.26(7) 4_666 . ?
O8 Nd1 O14 73.04(7) 1_656 . ?
O1 Nd1 O14 139.75(7) . . ?
O15 Nd1 O14 143.56(7) . . ?
O13 Nd1 O14 73.85(7) . . ?
O2 Nd1 O14 127.92(7) . . ?
O4 Nd2 O9 67.64(7) . . ?
O4 Nd2 O10 131.50(7) . 3_667 ?
O9 Nd2 O10 65.77(7) . 3_667 ?
O4 Nd2 O12 82.37(7) . 3_767 ?
O9 Nd2 O12 74.33(7) . 3_767 ?
O10 Nd2 O12 73.00(7) 3_667 3_767 ?
O4 Nd2 N1 137.50(7) . . ?
O9 Nd2 N1 123.81(7) . . ?
O10 Nd2 N1 81.82(7) 3_667 . ?
O12 Nd2 N1 138.77(7) 3_767 . ?
O4 Nd2 O11 71.57(7) . . ?
O9 Nd2 O11 125.28(7) . . ?
O10 Nd2 O11 128.64(6) 3_667 . ?
O12 Nd2 O11 65.41(7) 3_767 . ?
N1 Nd2 O11 110.88(8) . . ?
O4 Nd2 O5 91.15(7) . . ?
O9 Nd2 O5 71.07(7) . . ?
O10 Nd2 O5 86.17(7) 3_667 . ?
O12 Nd2 O5 144.61(7) 3_767 . ?
N1 Nd2 O5 61.76(7) . . ?
O11 Nd2 O5 144.48(6) . . ?
O4 Nd2 O3 65.75(7) . . ?
O9 Nd2 O3 120.91(7) . . ?
O10 Nd2 O3 155.78(7) 3_667 . ?
O12 Nd2 O3 130.57(7) 3_767 . ?
N1 Nd2 O3 75.58(7) . . ?
O11 Nd2 O3 69.03(6) . . ?
O5 Nd2 O3 75.62(6) . . ?
O4 Nd2 N3 140.34(7) . . ?
O9 Nd2 N3 141.55(7) . . ?
O10 Nd2 N3 78.00(7) 3_667 . ?
O12 Nd2 N3 83.46(7) 3_767 . ?
N1 Nd2 N3 59.32(7) . . ?
O11 Nd2 N3 68.83(7) . . ?
O5 Nd2 N3 120.44(7) . . ?
O3 Nd2 N3 97.41(7) . . ?
C3 N1 C2 107.6(2) . . ?
C3 N1 Nd2 128.81(18) . . ?
C2 N1 Nd2 123.48(19) . . ?
C3 N2 C1 107.8(2) . . ?
C3 N2 H2 127.1 . . ?
C1 N2 H2 124.5 . . ?
C8 N3 C4 117.4(3) . . ?
C8 N3 Nd2 123.4(2) . . ?
C4 N3 Nd2 118.28(18) . . ?
C13 O1 Nd1 121.27(19) . . ?
C14 O2 Nd1 119.39(18) . . ?
C14 O3 Nd2 114.01(17) . . ?
C13 O4 Nd2 115.03(18) . . ?
C10 O5 Nd2 125.78(17) . . ?
C10 O6 Nd1 147.94(19) . 4_465 ?
C9 O7 Nd1 147.56(18) . 4_465 ?
C9 O8 Nd1 122.99(17) . 1_454 ?
C11 O9 Nd2 119.48(18) . . ?
C11 O10 Nd2 118.72(17) . 3_667 ?
C12 O11 Nd2 117.55(18) . . ?
C12 O12 Nd2 117.61(17) . 3_767 ?
Nd1 O13 H13A 128.2 . . ?
Nd1 O13 H13B 121.4 . . ?
H13A O13 H13B 107.3 . . ?
Nd1 O14 H14A 118.5 . . ?
Nd1 O14 H14B 111.8 . . ?
H14A O14 H14B 107.5 . . ?
Nd1 O15 H15A 118.9 . . ?
Nd1 O15 H15B 113.1 . . ?
H15A O15 H15B 107.1 . . ?
H16B O16 H16A 107.3 . . ?
H17B O17 H17A 107.4 . . ?
C2 C1 N2 105.7(2) . . ?
C2 C1 C9 135.4(3) . . ?
N2 C1 C9 118.8(3) . . ?
N1 C2 C1 108.8(2) . . ?
N1 C2 C10 114.4(2) . . ?
C1 C2 C10 136.8(3) . . ?
N1 C3 N2 110.2(2) . . ?
N1 C3 C4 120.1(3) . . ?
N2 C3 C4 129.8(3) . . ?
N3 C4 C5 123.2(3) . . ?
N3 C4 C3 112.3(3) . . ?
C5 C4 C3 124.5(3) . . ?
C4 C5 C6 118.2(3) . . ?
C4 C5 H5 120.9 . . ?
C6 C5 H5 120.9 . . ?
C7 C6 C5 118.8(3) . . ?
C7 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
C6 C7 C8 119.7(3) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
N3 C8 C7 122.6(3) . . ?
N3 C8 H8 118.7 . . ?
C7 C8 H8 118.7 . . ?
O8 C9 O7 124.9(3) . . ?
O8 C9 C1 115.3(2) . . ?
O7 C9 C1 119.7(3) . . ?
O6 C10 O5 123.2(3) . . ?
O6 C10 C2 123.3(3) . . ?
O5 C10 C2 113.5(2) . . ?
O9 C11 O10 126.6(3) . . ?
O9 C11 C11 116.8(3) . 3_667 ?
O10 C11 C11 116.6(3) . 3_667 ?
O11 C12 O12 126.7(3) . . ?
O11 C12 C12 117.3(3) . 3_767 ?
O12 C12 C12 115.9(3) . 3_767 ?
O1 C13 O4 126.4(3) . . ?
O1 C13 C14 117.2(2) . . ?
O4 C13 C14 116.4(2) . . ?
O3 C14 O2 126.6(3) . . ?
O3 C14 C13 117.5(2) . . ?
O2 C14 C13 115.9(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N2 C1 C2 0.3(3) . . . . ?
C3 N2 C1 C9 -175.9(2) . . . . ?
C3 N1 C2 C1 0.2(3) . . . . ?
Nd2 N1 C2 C1 -176.93(17) . . . . ?
C3 N1 C2 C10 -179.0(2) . . . . ?
Nd2 N1 C2 C10 3.9(3) . . . . ?
N2 C1 C2 N1 -0.3(3) . . . . ?
C9 C1 C2 N1 175.0(3) . . . . ?
N2 C1 C2 C10 178.6(3) . . . . ?
C9 C1 C2 C10 -6.1(6) . . . . ?
C2 N1 C3 N2 0.0(3) . . . . ?
Nd2 N1 C3 N2 176.94(17) . . . . ?
C2 N1 C3 C4 -179.6(2) . . . . ?
Nd2 N1 C3 C4 -2.7(4) . . . . ?
C1 N2 C3 N1 -0.2(3) . . . . ?
C1 N2 C3 C4 179.3(3) . . . . ?
C8 N3 C4 C5 2.4(4) . . . . ?
Nd2 N3 C4 C5 -167.1(2) . . . . ?
C8 N3 C4 C3 -178.4(2) . . . . ?
Nd2 N3 C4 C3 12.0(3) . . . . ?
N1 C3 C4 N3 -7.1(4) . . . . ?
N2 C3 C4 N3 173.4(3) . . . . ?
N1 C3 C4 C5 172.0(3) . . . . ?
N2 C3 C4 C5 -7.5(5) . . . . ?
N3 C4 C5 C6 -2.0(5) . . . . ?
C3 C4 C5 C6 179.0(3) . . . . ?
C4 C5 C6 C7 0.0(5) . . . . ?
C5 C6 C7 C8 1.4(5) . . . . ?
C4 N3 C8 C7 -0.9(4) . . . . ?
Nd2 N3 C8 C7 168.1(2) . . . . ?
C6 C7 C8 N3 -1.0(5) . . . . ?
Nd1 O8 C9 O7 -5.8(4) 1_454 . . . ?
Nd1 O8 C9 C1 173.28(16) 1_454 . . . ?
Nd1 O7 C9 O8 134.2(3) 4_465 . . . ?
Nd1 O7 C9 C1 -44.8(5) 4_465 . . . ?
C2 C1 C9 O8 -167.1(3) . . . . ?
N2 C1 C9 O8 7.7(4) . . . . ?
C2 C1 C9 O7 12.1(5) . . . . ?
N2 C1 C9 O7 -173.1(2) . . . . ?
Nd1 O6 C10 O5 -164.9(2) 4_465 . . . ?
Nd1 O6 C10 C2 16.3(5) 4_465 . . . ?
Nd2 O5 C10 O6 169.83(19) . . . . ?
Nd2 O5 C10 C2 -11.3(3) . . . . ?
N1 C2 C10 O6 -176.7(2) . . . . ?
C1 C2 C10 O6 4.4(5) . . . . ?
N1 C2 C10 O5 4.5(3) . . . . ?
C1 C2 C10 O5 -174.4(3) . . . . ?
Nd2 O9 C11 O10 -167.1(2) . . . . ?
Nd2 O9 C11 C11 12.6(4) . . . 3_667 ?
Nd2 O10 C11 O9 -167.4(2) 3_667 . . . ?
Nd2 O10 C11 C11 12.8(4) 3_667 . . 3_667 ?
Nd2 O11 C12 O12 160.2(2) . . . . ?
Nd2 O11 C12 C12 -18.2(4) . . . 3_767 ?
Nd2 O12 C12 O11 161.2(2) 3_767 . . . ?
Nd2 O12 C12 C12 -20.4(4) 3_767 . . 3_767 ?
Nd1 O1 C13 O4 176.9(2) . . . . ?
Nd1 O1 C13 C14 -5.2(3) . . . . ?
Nd2 O4 C13 O1 145.6(2) . . . . ?
Nd2 O4 C13 C14 -32.3(3) . . . . ?
Nd2 O3 C14 O2 -160.8(2) . . . . ?
Nd2 O3 C14 C13 17.6(3) . . . . ?
Nd1 O2 C14 O3 168.9(2) . . . . ?
Nd1 O2 C14 C13 -9.5(3) . . . . ?
O1 C13 C14 O3 -168.8(2) . . . . ?
O4 C13 C14 O3 9.4(4) . . . . ?
O1 C13 C14 O2 9.8(4) . . . . ?
O4 C13 C14 O2 -172.0(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O10 0.86 2.06 2.859(3) 153.8 1_554
O13 H13A O12 0.82 2.00 2.809(3) 170.5 .
O13 H13B O5 0.82 2.02 2.799(3) 157.4 1_655
O14 H14A O16 0.82 2.19 2.990(4) 166.8 4_666
O14 H14B O5 0.82 1.92 2.736(3) 170.8 1_655
O15 H15A O17 0.82 2.05 2.831(3) 158.9 1_556
O15 H15B O2 0.82 1.90 2.716(3) 171.8 4_566
O16 H16B O4 0.82 2.13 2.909(4) 159.3 4_565
O16 H16A O17 0.82 2.11 2.824(4) 145.1 1_556
O17 H17B O14 0.82 2.14 2.960(3) 176.9 1_454
O17 H17A O3 0.82 2.10 2.919(3) 175.6 4_565

_refine_diff_density_max         0.896
_refine_diff_density_min         -1.093
_refine_diff_density_rms         0.116

####################################################################### 
# 
# 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_Z2-Ce-zb22-14R1
_database_code_depnum_ccdc_archive 'CCDC 1506098'
_audit_update_record             
;
2017-02-28 deposited with the CCDC.
2017-03-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H7 Ce N3 O7'
_chemical_formula_weight         433.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ce Ce -0.1870 2.7090 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   7.0860(14)
_cell_length_b                   19.480(4)
_cell_length_c                   8.6770(17)
_cell_angle_alpha                90
_cell_angle_beta                 92.55(3)
_cell_angle_gamma                90
_cell_volume                     1196.5(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7027
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      31.97

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.405
_exptl_crystal_F_000             832
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    3.957
_shelx_estimated_absorpt_T_min   0.338
_shelx_estimated_absorpt_T_max   0.438
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3459
_exptl_absorpt_correction_T_max  0.4461
_exptl_absorpt_process_details   '(HKL SCALEPACK; Otwinowski & Minor, 1997)'

_exptl_special_details           ?

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.700
_diffrn_radiation_type           synchrotron
_diffrn_source                   'synchrotron, 3W1A at BSRF'
_diffrn_measurement_device_type  mar165
_diffrn_measurement_method       'oscillation mode'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4513
_diffrn_reflns_av_unetI/netI     0.0538
_diffrn_reflns_av_R_equivalents  0.0566
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.533
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        24.835
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2447
_reflns_number_gt                2268
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0487P)²+0.1362P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2447
_refine_ls_number_parameters     205
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0280
_refine_ls_wR_factor_ref         0.0780
_refine_ls_wR_factor_gt          0.0760
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ce1 Ce 0.31429(2) 0.14787(2) 0.89750(2) 0.00772(10) Uani 1 1 d . . . . .
O1 O 0.5355(3) 0.17066(12) 0.1193(2) 0.0144(4) Uani 1 1 d . . . . .
O2 O 0.6363(3) 0.26048(12) 0.2603(2) 0.0193(5) Uani 1 1 d . . . . .
O3 O 0.6495(3) 0.29099(13) 0.5930(2) 0.0178(5) Uani 1 1 d . . . . .
O4 O 0.5476(3) 0.22979(12) 0.7892(2) 0.0184(5) Uani 1 1 d . . . . .
O5 O 0.4075(3) -0.06358(10) 1.1170(2) 0.0113(4) Uani 1 1 d . . . . .
O6 O 0.3029(3) 0.04282(11) 1.0707(2) 0.0102(4) Uani 1 1 d . . . . .
O7 O -0.0505(4) 0.12373(16) 0.8830(4) 0.0287(6) Uani 1 1 d . . . . .
H7A H -0.139(7) 0.094(3) 0.873(5) 0.043 Uiso 1 1 d . U . . .
H7B H -0.094(8) 0.155(3) 0.935(7) 0.043 Uiso 1 1 d . U . . .
N1 N 0.2097(4) 0.02257(14) 0.7125(3) 0.0132(5) Uani 1 1 d . . . . .
N2 N 0.3976(4) 0.13323(13) 0.6172(3) 0.0098(5) Uani 1 1 d . . . . .
N3 N 0.3924(3) 0.10702(13) 0.3715(3) 0.0099(5) Uani 1 1 d . . . . .
H3A H 0.368700 0.089313 0.281969 0.012 Uiso 1 1 d R U . . .
C1 C 0.1266(4) -0.03405(17) 0.7650(3) 0.0136(6) Uani 1 1 d . . . . .
H1 H 0.092645 -0.034622 0.869661 0.016 Uiso 1 1 calc R U . . .
C2 C 0.0872(4) -0.09155(17) 0.6767(4) 0.0175(6) Uani 1 1 d . . . . .
H2 H 0.027819 -0.130379 0.719734 0.021 Uiso 1 1 calc R U . . .
C3 C 0.1366(4) -0.09148(16) 0.5218(4) 0.0157(6) Uani 1 1 d . . . . .
H3 H 0.112018 -0.130345 0.457939 0.019 Uiso 1 1 calc R U . . .
C4 C 0.2225(4) -0.03328(17) 0.4640(4) 0.0120(6) Uani 1 1 d . . . . .
H4 H 0.257949 -0.031765 0.359763 0.014 Uiso 1 1 calc R U . . .
C5 C 0.2557(4) 0.02287(15) 0.5614(3) 0.0095(6) Uani 1 1 d . . . . .
C6 C 0.3447(4) 0.08681(16) 0.5142(3) 0.0102(5) Uani 1 1 d . . . . .
C7 C 0.4829(4) 0.16971(16) 0.3855(3) 0.0102(6) Uani 1 1 d . . . . .
C8 C 0.4859(4) 0.18523(15) 0.5420(3) 0.0107(6) Uani 1 1 d . . . . .
C9 C 0.5568(4) 0.20335(16) 0.2447(3) 0.0123(6) Uani 1 1 d . . . . .
C10 C 0.5675(4) 0.23989(17) 0.6471(3) 0.0125(6) Uani 1 1 d . . . . .
C11 C 0.4164(4) -0.00631(15) 1.0542(3) 0.0089(6) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ce1 O3 2.415(2) 4_566 ?
Ce1 O2 2.462(2) 4_566 ?
Ce1 O1 2.468(2) 1_556 ?
Ce1 O4 2.510(2) . ?
Ce1 O6 2.542(2) . ?
Ce1 N2 2.545(3) . ?
Ce1 O5 2.573(2) 3_657 ?
Ce1 O7 2.625(3) . ?
Ce1 N1 2.996(3) . ?
O1 C9 1.264(4) . ?
O2 C9 1.252(4) . ?
O3 C10 1.254(4) . ?
O4 C10 1.263(3) . ?
O5 C11 1.244(3) . ?
O6 C11 1.262(4) . ?
O7 H7A 0.86(5) . ?
O7 H7B 0.82(5) . ?
N1 C1 1.340(4) . ?
N1 C5 1.365(4) . ?
N2 C6 1.314(4) . ?
N2 C8 1.371(4) . ?
N3 C6 1.356(4) . ?
N3 C7 1.382(4) . ?
N3 H3A 0.8601 . ?
C1 C2 1.378(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.404(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.391(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.396(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.463(4) . ?
C7 C8 1.391(4) . ?
C7 C9 1.500(4) . ?
C8 C10 1.500(4) . ?
C11 C11 1.565(6) 3_657 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 Ce1 O2 74.26(7) 4_566 4_566 ?
O3 Ce1 O1 70.96(8) 4_566 1_556 ?
O2 Ce1 O1 122.73(8) 4_566 1_556 ?
O3 Ce1 O4 107.24(8) 4_566 . ?
O2 Ce1 O4 71.94(8) 4_566 . ?
O1 Ce1 O4 76.79(7) 1_556 . ?
O3 Ce1 O6 87.30(7) 4_566 . ?
O2 Ce1 O6 147.19(8) 4_566 . ?
O1 Ce1 O6 73.71(7) 1_556 . ?
O4 Ce1 O6 140.50(7) . . ?
O3 Ce1 N2 150.05(8) 4_566 . ?
O2 Ce1 N2 75.80(8) 4_566 . ?
O1 Ce1 N2 126.83(8) 1_556 . ?
O4 Ce1 N2 61.89(8) . . ?
O6 Ce1 N2 119.32(7) . . ?
O3 Ce1 O5 138.10(7) 4_566 3_657 ?
O2 Ce1 O5 144.71(7) 4_566 3_657 ?
O1 Ce1 O5 72.03(7) 1_556 3_657 ?
O4 Ce1 O5 82.45(8) . 3_657 ?
O6 Ce1 O5 63.87(7) . 3_657 ?
N2 Ce1 O5 70.78(8) . 3_657 ?
O3 Ce1 O7 67.43(10) 4_566 . ?
O2 Ce1 O7 67.94(9) 4_566 . ?
O1 Ce1 O7 131.27(9) 1_556 . ?
O4 Ce1 O7 139.43(9) . . ?
O6 Ce1 O7 80.05(8) . . ?
N2 Ce1 O7 101.77(9) . . ?
O5 Ce1 O7 129.66(8) 3_657 . ?
O3 Ce1 N1 131.45(8) 4_566 . ?
O2 Ce1 N1 102.85(7) 4_566 . ?
O1 Ce1 N1 134.25(7) 1_556 . ?
O4 Ce1 N1 117.95(7) . . ?
O6 Ce1 N1 69.35(7) . . ?
N2 Ce1 N1 57.25(8) . . ?
O5 Ce1 N1 68.02(7) 3_657 . ?
O7 Ce1 N1 66.97(9) . . ?
C9 O1 Ce1 144.0(2) . 1_554 ?
C9 O2 Ce1 156.21(19) . 4_665 ?
C10 O3 Ce1 154.2(2) . 4_665 ?
C10 O4 Ce1 124.65(19) . . ?
C11 O5 Ce1 119.80(18) . 3_657 ?
C11 O6 Ce1 120.42(18) . . ?
Ce1 O7 H7A 147(3) . . ?
Ce1 O7 H7B 103(4) . . ?
H7A O7 H7B 106(5) . . ?
C1 N1 C5 117.2(3) . . ?
C1 N1 Ce1 126.2(2) . . ?
C5 N1 Ce1 116.56(19) . . ?
C6 N2 C8 107.9(2) . . ?
C6 N2 Ce1 131.0(2) . . ?
C8 N2 Ce1 120.13(18) . . ?
C6 N3 C7 108.1(2) . . ?
C6 N3 H3A 131.4 . . ?
C7 N3 H3A 120.3 . . ?
N1 C1 C2 124.2(3) . . ?
N1 C1 H1 117.9 . . ?
C2 C1 H1 117.9 . . ?
C1 C2 C3 118.6(3) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C4 C3 C2 118.6(3) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
C3 C4 C5 119.0(3) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
N1 C5 C4 122.5(3) . . ?
N1 C5 C6 113.4(3) . . ?
C4 C5 C6 124.1(3) . . ?
N2 C6 N3 110.2(3) . . ?
N2 C6 C5 120.6(3) . . ?
N3 C6 C5 129.1(3) . . ?
N3 C7 C8 105.3(2) . . ?
N3 C7 C9 119.5(2) . . ?
C8 C7 C9 135.2(3) . . ?
N2 C8 C7 108.4(3) . . ?
N2 C8 C10 114.0(2) . . ?
C7 C8 C10 137.4(3) . . ?
O2 C9 O1 125.2(3) . . ?
O2 C9 C7 118.2(3) . . ?
O1 C9 C7 116.6(3) . . ?
O3 C10 O4 124.2(3) . . ?
O3 C10 C8 120.6(2) . . ?
O4 C10 C8 115.2(3) . . ?
O5 C11 O6 125.8(3) . . ?
O5 C11 C11 117.3(3) . 3_657 ?
O6 C11 C11 116.9(3) . 3_657 ?

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
C5 N1 C1 C2 0.7(4) . . . . ?
Ce1 N1 C1 C2 -177.6(2) . . . . ?
N1 C1 C2 C3 0.1(5) . . . . ?
C1 C2 C3 C4 -0.3(4) . . . . ?
C2 C3 C4 C5 -0.2(4) . . . . ?
C1 N1 C5 C4 -1.2(4) . . . . ?
Ce1 N1 C5 C4 177.2(2) . . . . ?
C1 N1 C5 C6 179.7(3) . . . . ?
Ce1 N1 C5 C6 -1.9(3) . . . . ?
C3 C4 C5 N1 1.0(4) . . . . ?
C3 C4 C5 C6 -180.0(3) . . . . ?
C8 N2 C6 N3 -1.1(3) . . . . ?
Ce1 N2 C6 N3 167.40(19) . . . . ?
C8 N2 C6 C5 176.4(3) . . . . ?
Ce1 N2 C6 C5 -15.1(4) . . . . ?
C7 N3 C6 N2 0.7(3) . . . . ?
C7 N3 C6 C5 -176.5(3) . . . . ?
N1 C5 C6 N2 9.6(4) . . . . ?
C4 C5 C6 N2 -169.5(3) . . . . ?
N1 C5 C6 N3 -173.5(3) . . . . ?
C4 C5 C6 N3 7.4(5) . . . . ?
C6 N3 C7 C8 0.0(3) . . . . ?
C6 N3 C7 C9 178.2(3) . . . . ?
C6 N2 C8 C7 1.1(3) . . . . ?
Ce1 N2 C8 C7 -168.90(19) . . . . ?
C6 N2 C8 C10 -175.7(3) . . . . ?
Ce1 N2 C8 C10 14.4(3) . . . . ?
N3 C7 C8 N2 -0.6(3) . . . . ?
C9 C7 C8 N2 -178.4(3) . . . . ?
N3 C7 C8 C10 174.9(3) . . . . ?
C9 C7 C8 C10 -2.9(6) . . . . ?
Ce1 O2 C9 O1 -152.8(4) 4_665 . . . ?
Ce1 O2 C9 C7 26.1(7) 4_665 . . . ?
Ce1 O1 C9 O2 -95.3(4) 1_554 . . . ?
Ce1 O1 C9 C7 85.7(4) 1_554 . . . ?
N3 C7 C9 O2 179.2(3) . . . . ?
C8 C7 C9 O2 -3.2(5) . . . . ?
N3 C7 C9 O1 -1.8(4) . . . . ?
C8 C7 C9 O1 175.8(3) . . . . ?
Ce1 O3 C10 O4 158.4(3) 4_665 . . . ?
Ce1 O3 C10 C8 -21.2(7) 4_665 . . . ?
Ce1 O4 C10 O3 162.5(2) . . . . ?
Ce1 O4 C10 C8 -17.9(4) . . . . ?
N2 C8 C10 O3 -178.8(3) . . . . ?
C7 C8 C10 O3 5.8(6) . . . . ?
N2 C8 C10 O4 1.5(4) . . . . ?
C7 C8 C10 O4 -173.8(3) . . . . ?
Ce1 O5 C11 O6 -169.5(2) 3_657 . . . ?
Ce1 O5 C11 C11 10.1(4) 3_657 . . 3_657 ?
Ce1 O6 C11 O5 -169.6(2) . . . . ?
Ce1 O6 C11 C11 10.8(4) . . . 3_657 ?

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 H7A O5 0.86(5) 1.99(5) 2.788(3) 152(5) 3_557
O7 H7B O3 0.82(5) 2.40(6) 2.803(4) 111(5) 4_566
N3 H3A O6 0.86 2.08 2.938(3) 177.1 1_554

_refine_diff_density_max         1.017
_refine_diff_density_min         -1.222
_refine_diff_density_rms         0.162

####################################################################### 
# 
# 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_Z11-Er-zb217-14R1
_database_code_depnum_ccdc_archive 'CCDC 1506107'
_audit_update_record             
;
2017-02-28 deposited with the CCDC.
2017-03-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H15 Er2 N3 O17'
_chemical_formula_weight         831.81

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Er Er -0.2586 4.9576 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   9.4056(6)
_cell_length_b                   22.3152(15)
_cell_length_c                   10.0820(7)
_cell_angle_alpha                90
_cell_angle_beta                 102.960(2)
_cell_angle_gamma                90
_cell_volume                     2062.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9627
_cell_measurement_theta_min      2.88
_cell_measurement_theta_max      28.33

_exptl_crystal_description       block
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.679
_exptl_crystal_F_000             1568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_exptl_absorpt_coefficient_mu    8.182
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7636
_exptl_absorpt_correction_T_max  0.8476
_exptl_absorpt_process_details   'SADABS (Bruker, 2000)'

_exptl_special_details           ?

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17004
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.829
_diffrn_reflns_theta_max         25.993
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4030
_reflns_number_gt                3474
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0206P)²+3.7936P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4030
_refine_ls_number_parameters     326
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0238
_refine_ls_wR_factor_ref         0.0537
_refine_ls_wR_factor_gt          0.0507
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Er1 Er 1.24787(2) 0.27613(2) 1.05256(2) 0.01354(7) Uani 1 1 d . . . . .
Er2 Er 0.71757(2) 0.43395(2) 0.86311(2) 0.01226(6) Uani 1 1 d . . . . .
N1 N 0.5998(4) 0.41516(17) 0.6297(4) 0.0141(8) Uani 1 1 d . . . . .
N2 N 0.5329(4) 0.41262(18) 0.4072(4) 0.0156(9) Uani 1 1 d . . . . .
H2 H 0.518669 0.422166 0.322733 0.023 Uiso 1 1 d R U . . .
N3 N 0.7766(5) 0.5085(2) 0.6505(5) 0.0257(11) Uani 1 1 d . . . . .
O1 O 1.0664(4) 0.33652(16) 1.1143(4) 0.0227(8) Uani 1 1 d . . . . .
O2 O 1.0294(4) 0.28574(16) 0.8708(4) 0.0228(8) Uani 1 1 d . . . . .
O3 O 0.8273(4) 0.34105(15) 0.7984(4) 0.0226(8) Uani 1 1 d . . . . .
O4 O 0.8499(4) 0.38093(16) 1.0522(4) 0.0228(8) Uani 1 1 d . . . . .
O5 O 0.5233(4) 0.36042(15) 0.8268(3) 0.0169(7) Uani 1 1 d . . . . .
O9 O 0.6019(4) 0.43630(15) 1.0539(3) 0.0199(8) Uani 1 1 d . . . . .
O6 O 0.3801(4) 0.29478(16) 0.6977(4) 0.0222(8) Uani 1 1 d . . . . .
O7 O 0.2731(4) 0.29258(15) 0.3966(4) 0.0198(8) Uani 1 1 d . . . . .
O8 O 0.3646(4) 0.33489(15) 0.2336(3) 0.0189(8) Uani 1 1 d . . . . .
O10 O 0.4689(4) 0.49216(15) 1.1630(3) 0.0183(7) Uani 1 1 d . . . . .
O11 O 0.9743(4) 0.44671(15) 0.8708(4) 0.0209(8) Uani 1 1 d . . . . .
O12 O 1.1809(4) 0.48236(15) 1.0010(4) 0.0239(9) Uani 1 1 d . . . . .
O13 O 1.2737(4) 0.36667(16) 0.9384(4) 0.0274(9) Uani 1 1 d . . . . .
H13A H 1.241351 0.400568 0.942662 0.041 Uiso 1 1 d R U . . .
H13B H 1.345211 0.369824 0.905055 0.041 Uiso 1 1 d R U . . .
O14 O 1.5013(4) 0.28315(17) 1.0358(4) 0.0290(9) Uani 1 1 d . . . . .
H14A H 1.556024 0.296089 1.104826 0.044 Uiso 1 1 d R U . . .
H14B H 1.515323 0.303183 0.971673 0.044 Uiso 1 1 d R U . . .
O15 O 1.0840(4) 0.20944(16) 1.1145(4) 0.0279(9) Uani 1 1 d . . . . .
H15A H 1.000016 0.207750 1.069173 0.042 Uiso 1 1 d R U . . .
H15B H 1.079156 0.208011 1.194607 0.042 Uiso 1 1 d R U . . .
O16 O 0.7320(7) 0.1739(3) 0.7581(7) 0.089(2) Uani 1 1 d . U . . .
O17 O 0.7854(6) 0.2142(3) 0.0311(6) 0.0686(16) Uani 1 1 d . . . . .
C1 C 0.4537(5) 0.3682(2) 0.4534(5) 0.0133(10) Uani 1 1 d . . . . .
C2 C 0.4991(5) 0.3705(2) 0.5944(5) 0.0118(10) Uani 1 1 d . . . . .
C3 C 0.6187(5) 0.4400(2) 0.5161(5) 0.0150(10) Uani 1 1 d . . . . .
C4 C 0.7228(5) 0.4892(2) 0.5211(5) 0.0169(10) Uani 1 1 d . . . . .
C5 C 0.7651(6) 0.5120(3) 0.4077(6) 0.0299(13) Uani 1 1 d . . . . .
H5 H 0.729121 0.496056 0.321482 0.036 Uiso 1 1 calc R U . . .
C6 C 0.8636(7) 0.5598(3) 0.4277(7) 0.0401(16) Uani 1 1 d . . . . .
H6 H 0.893765 0.577353 0.354969 0.048 Uiso 1 1 calc R U . . .
C7 C 0.9149(7) 0.5802(3) 0.5596(7) 0.0397(17) Uani 1 1 d . . . . .
H7 H 0.979283 0.612382 0.576008 0.048 Uiso 1 1 calc R U . . .
C8 C 0.8717(7) 0.5535(3) 0.6649(7) 0.0335(14) Uani 1 1 d . . . . .
H8 H 0.910802 0.567469 0.752393 0.040 Uiso 1 1 calc R U . . .
C9 C 0.3558(5) 0.3288(2) 0.3547(5) 0.0157(10) Uani 1 1 d . . . . .
C10 C 0.4633(5) 0.3385(2) 0.7104(5) 0.0129(10) Uani 1 1 d . . . . .
C11 C 0.5206(5) 0.4793(2) 1.0634(5) 0.0148(10) Uani 1 1 d . . . . .
C12 C 1.0444(5) 0.4796(2) 0.9613(5) 0.0174(11) Uani 1 1 d . . . . .
C13 C 0.9518(5) 0.3482(2) 1.0311(5) 0.0189(11) Uani 1 1 d . . . . .
C14 C 0.9333(5) 0.3229(2) 0.8857(5) 0.0185(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
Er1 O7 2.246(3) 4_666 ?
Er1 O8 2.315(3) 1_656 ?
Er1 O6 2.319(3) 4_666 ?
Er1 O15 2.326(4) . ?
Er1 O13 2.364(4) . ?
Er1 O1 2.365(3) . ?
Er1 O14 2.433(4) . ?
Er1 O2 2.436(3) . ?
Er2 O4 2.349(3) . ?
Er2 O10 2.378(3) 3_667 ?
Er2 O12 2.385(3) 3_767 ?
Er2 N1 2.402(4) . ?
Er2 O9 2.413(4) . ?
Er2 O11 2.415(3) . ?
Er2 O5 2.422(3) . ?
Er2 O3 2.468(3) . ?
Er2 N3 2.864(5) . ?
N1 C3 1.320(6) . ?
N1 C2 1.367(6) . ?
N2 C3 1.354(6) . ?
N2 C1 1.382(6) . ?
N2 H2 0.8587 . ?
N3 C8 1.331(7) . ?
N3 C4 1.359(7) . ?
O1 C13 1.236(6) . ?
O2 C14 1.260(6) . ?
O3 C14 1.241(6) . ?
O4 C13 1.260(6) . ?
O5 C10 1.280(6) . ?
O9 C11 1.245(6) . ?
O6 C10 1.240(5) . ?
O7 C9 1.259(6) . ?
O8 C9 1.249(6) . ?
O10 C11 1.244(6) . ?
O11 C12 1.239(6) . ?
O12 C12 1.258(6) . ?
O13 H13A 0.8200 . ?
O13 H13B 0.8200 . ?
O14 H14A 0.8199 . ?
O14 H14B 0.8201 . ?
O15 H15A 0.8200 . ?
O15 H15B 0.8201 . ?
C1 C2 1.391(6) . ?
C1 C9 1.483(6) . ?
C2 C10 1.471(6) . ?
C3 C4 1.465(6) . ?
C4 C5 1.389(7) . ?
C5 C6 1.398(8) . ?
C5 H5 0.9300 . ?
C6 C7 1.385(9) . ?
C6 H6 0.9300 . ?
C7 C8 1.357(9) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C11 C11 1.552(10) 3_667 ?
C12 C12 1.559(10) 3_767 ?
C13 C14 1.545(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O7 Er1 O8 146.39(12) 4_666 1_656 ?
O7 Er1 O6 81.39(12) 4_666 4_666 ?
O8 Er1 O6 78.25(12) 1_656 4_666 ?
O7 Er1 O15 86.07(14) 4_666 . ?
O8 Er1 O15 112.11(13) 1_656 . ?
O6 Er1 O15 71.81(13) 4_666 . ?
O7 Er1 O13 101.77(13) 4_666 . ?
O8 Er1 O13 79.49(13) 1_656 . ?
O6 Er1 O13 142.31(13) 4_666 . ?
O15 Er1 O13 145.47(13) . . ?
O7 Er1 O1 140.24(12) 4_666 . ?
O8 Er1 O1 73.28(12) 1_656 . ?
O6 Er1 O1 122.63(12) 4_666 . ?
O15 Er1 O1 74.53(13) . . ?
O13 Er1 O1 78.47(13) . . ?
O7 Er1 O14 74.72(13) 4_666 . ?
O8 Er1 O14 73.71(13) 1_656 . ?
O6 Er1 O14 72.10(13) 4_666 . ?
O15 Er1 O14 141.12(13) . . ?
O13 Er1 O14 72.66(12) . . ?
O1 Er1 O14 139.29(13) . . ?
O7 Er1 O2 74.76(12) 4_666 . ?
O8 Er1 O2 135.57(12) 1_656 . ?
O6 Er1 O2 141.01(13) 4_666 . ?
O15 Er1 O2 76.14(13) . . ?
O13 Er1 O2 73.74(13) . . ?
O1 Er1 O2 67.12(12) . . ?
O14 Er1 O2 128.04(13) . . ?
O4 Er2 O10 133.03(12) . 3_667 ?
O4 Er2 O12 81.80(13) . 3_767 ?
O10 Er2 O12 73.22(12) 3_667 3_767 ?
O4 Er2 N1 138.67(13) . . ?
O10 Er2 N1 81.14(12) 3_667 . ?
O12 Er2 N1 137.43(13) 3_767 . ?
O4 Er2 O9 67.39(11) . . ?
O10 Er2 O9 67.68(11) 3_667 . ?
O12 Er2 O9 73.70(12) 3_767 . ?
N1 Er2 O9 126.39(13) . . ?
O4 Er2 O11 71.91(13) . . ?
O10 Er2 O11 128.98(12) 3_667 . ?
O12 Er2 O11 67.71(12) 3_767 . ?
N1 Er2 O11 106.86(13) . . ?
O9 Er2 O11 126.72(12) . . ?
O4 Er2 O5 91.48(12) . . ?
O10 Er2 O5 86.57(12) 3_667 . ?
O12 Er2 O5 143.96(12) 3_767 . ?
N1 Er2 O5 64.35(12) . . ?
O9 Er2 O5 71.07(11) . . ?
O11 Er2 O5 143.10(11) . . ?
O4 Er2 O3 67.32(12) . . ?
O10 Er2 O3 153.47(11) 3_667 . ?
O12 Er2 O3 132.24(11) 3_767 . ?
N1 Er2 O3 73.90(12) . . ?
O9 Er2 O3 121.24(12) . . ?
O11 Er2 O3 68.49(11) . . ?
O5 Er2 O3 74.74(12) . . ?
O4 Er2 N3 138.03(13) . . ?
O10 Er2 N3 77.09(12) 3_667 . ?
O12 Er2 N3 81.69(13) 3_767 . ?
N1 Er2 N3 59.49(12) . . ?
O9 Er2 N3 141.42(12) . . ?
O11 Er2 N3 66.13(12) . . ?
O5 Er2 N3 123.13(11) . . ?
O3 Er2 N3 97.31(13) . . ?
C3 N1 C2 107.5(4) . . ?
C3 N1 Er2 130.9(3) . . ?
C2 N1 Er2 121.5(3) . . ?
C3 N2 C1 108.6(4) . . ?
C3 N2 H2 128.7 . . ?
C1 N2 H2 122.4 . . ?
C8 N3 C4 116.1(5) . . ?
C8 N3 Er2 126.5(4) . . ?
C4 N3 Er2 116.2(3) . . ?
C13 O1 Er1 120.8(3) . . ?
C14 O2 Er1 118.4(3) . . ?
C14 O3 Er2 113.9(3) . . ?
C13 O4 Er2 116.1(3) . . ?
C10 O5 Er2 124.0(3) . . ?
C11 O9 Er2 118.2(3) . . ?
C10 O6 Er1 147.0(3) . 4_465 ?
C9 O7 Er1 147.5(3) . 4_465 ?
C9 O8 Er1 125.8(3) . 1_454 ?
C11 O10 Er2 118.8(3) . 3_667 ?
C12 O11 Er2 117.2(3) . . ?
C12 O12 Er2 118.1(3) . 3_767 ?
Er1 O13 H13A 133.1 . . ?
Er1 O13 H13B 117.1 . . ?
H13A O13 H13B 106.9 . . ?
Er1 O14 H14A 113.7 . . ?
Er1 O14 H14B 115.0 . . ?
H14A O14 H14B 107.2 . . ?
Er1 O15 H15A 119.6 . . ?
Er1 O15 H15B 118.4 . . ?
H15A O15 H15B 106.7 . . ?
N2 C1 C2 104.7(4) . . ?
N2 C1 C9 120.0(4) . . ?
C2 C1 C9 135.2(4) . . ?
N1 C2 C1 109.2(4) . . ?
N1 C2 C10 114.5(4) . . ?
C1 C2 C10 136.2(4) . . ?
N1 C3 N2 110.1(4) . . ?
N1 C3 C4 120.3(4) . . ?
N2 C3 C4 129.7(5) . . ?
N3 C4 C5 124.1(5) . . ?
N3 C4 C3 111.8(5) . . ?
C5 C4 C3 124.0(5) . . ?
C4 C5 C6 117.6(6) . . ?
C4 C5 H5 121.2 . . ?
C6 C5 H5 121.2 . . ?
C7 C6 C5 117.8(6) . . ?
C7 C6 H6 121.1 . . ?
C5 C6 H6 121.1 . . ?
C8 C7 C6 120.4(5) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
N3 C8 C7 123.9(6) . . ?
N3 C8 H8 118.0 . . ?
C7 C8 H8 118.0 . . ?
O8 C9 O7 125.4(4) . . ?
O8 C9 C1 115.1(4) . . ?
O7 C9 C1 119.5(4) . . ?
O6 C10 O5 122.2(4) . . ?
O6 C10 C2 123.5(4) . . ?
O5 C10 C2 114.3(4) . . ?
O10 C11 O9 126.7(5) . . ?
O10 C11 C11 117.3(5) . 3_667 ?
O9 C11 C11 116.0(6) . 3_667 ?
O11 C12 O12 126.9(5) . . ?
O11 C12 C12 117.3(5) . 3_767 ?
O12 C12 C12 115.7(5) . 3_767 ?
O1 C13 O4 126.0(5) . . ?
O1 C13 C14 117.6(5) . . ?
O4 C13 C14 116.4(4) . . ?
O3 C14 O2 128.0(5) . . ?
O3 C14 C13 117.0(4) . . ?
O2 C14 C13 115.0(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
C3 N2 C1 C2 -0.9(5) . . . . ?
C3 N2 C1 C9 -176.9(4) . . . . ?
C3 N1 C2 C1 -0.5(5) . . . . ?
Er2 N1 C2 C1 -177.6(3) . . . . ?
C3 N1 C2 C10 -179.0(4) . . . . ?
Er2 N1 C2 C10 3.9(5) . . . . ?
N2 C1 C2 N1 0.8(5) . . . . ?
C9 C1 C2 N1 175.9(5) . . . . ?
N2 C1 C2 C10 178.9(5) . . . . ?
C9 C1 C2 C10 -6.0(10) . . . . ?
C2 N1 C3 N2 -0.1(5) . . . . ?
Er2 N1 C3 N2 176.6(3) . . . . ?
C2 N1 C3 C4 -179.1(4) . . . . ?
Er2 N1 C3 C4 -2.4(7) . . . . ?
C1 N2 C3 N1 0.6(6) . . . . ?
C1 N2 C3 C4 179.5(5) . . . . ?
C8 N3 C4 C5 2.4(8) . . . . ?
Er2 N3 C4 C5 -166.0(4) . . . . ?
C8 N3 C4 C3 -179.6(5) . . . . ?
Er2 N3 C4 C3 12.0(5) . . . . ?
N1 C3 C4 N3 -7.7(7) . . . . ?
N2 C3 C4 N3 173.5(5) . . . . ?
N1 C3 C4 C5 170.3(5) . . . . ?
N2 C3 C4 C5 -8.5(8) . . . . ?
N3 C4 C5 C6 -3.4(8) . . . . ?
C3 C4 C5 C6 178.9(5) . . . . ?
C4 C5 C6 C7 1.5(9) . . . . ?
C5 C6 C7 C8 1.1(10) . . . . ?
C4 N3 C8 C7 0.4(9) . . . . ?
Er2 N3 C8 C7 167.5(5) . . . . ?
C6 C7 C8 N3 -2.1(10) . . . . ?
Er1 O8 C9 O7 -5.8(7) 1_454 . . . ?
Er1 O8 C9 C1 173.8(3) 1_454 . . . ?
Er1 O7 C9 O8 135.1(5) 4_465 . . . ?
Er1 O7 C9 C1 -44.5(8) 4_465 . . . ?
N2 C1 C9 O8 7.5(7) . . . . ?
C2 C1 C9 O8 -166.9(5) . . . . ?
N2 C1 C9 O7 -172.8(4) . . . . ?
C2 C1 C9 O7 12.7(8) . . . . ?
Er1 O6 C10 O5 -172.1(4) 4_465 . . . ?
Er1 O6 C10 C2 9.3(9) 4_465 . . . ?
Er2 O5 C10 O6 169.0(3) . . . . ?
Er2 O5 C10 C2 -12.3(5) . . . . ?
N1 C2 C10 O6 -176.2(4) . . . . ?
C1 C2 C10 O6 5.8(9) . . . . ?
N1 C2 C10 O5 5.1(6) . . . . ?
C1 C2 C10 O5 -172.8(5) . . . . ?
Er2 O10 C11 O9 -168.7(4) 3_667 . . . ?
Er2 O10 C11 C11 10.8(7) 3_667 . . 3_667 ?
Er2 O9 C11 O10 -169.2(4) . . . . ?
Er2 O9 C11 C11 11.2(6) . . . 3_667 ?
Er2 O11 C12 O12 163.9(4) . . . . ?
Er2 O11 C12 C12 -13.7(7) . . . 3_767 ?
Er2 O12 C12 O11 165.2(4) 3_767 . . . ?
Er2 O12 C12 C12 -17.2(7) 3_767 . . 3_767 ?
Er1 O1 C13 O4 -178.2(4) . . . . ?
Er1 O1 C13 C14 -1.0(6) . . . . ?
Er2 O4 C13 O1 148.8(4) . . . . ?
Er2 O4 C13 C14 -28.5(6) . . . . ?
Er2 O3 C14 O2 -162.8(4) . . . . ?
Er2 O3 C14 C13 17.2(6) . . . . ?
Er1 O2 C14 O3 167.7(4) . . . . ?
Er1 O2 C14 C13 -12.3(6) . . . . ?
O1 C13 C14 O3 -170.9(5) . . . . ?
O4 C13 C14 O3 6.6(7) . . . . ?
O1 C13 C14 O2 9.1(7) . . . . ?
O4 C13 C14 O2 -173.4(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
O15 H15B O2 0.82 1.94 2.748(5) 167.7 4_566
O15 H15A O17 0.82 1.97 2.747(7) 157.0 1_556
O14 H14B O5 0.82 1.95 2.766(5) 170.0 1_655
O14 H14A O16 0.82 2.10 2.910(8) 167.4 4_666
O13 H13B O5 0.82 2.02 2.825(5) 169.0 1_655
O13 H13A O12 0.82 2.04 2.841(5) 166.5 .
N2 H2 O10 0.86 2.22 2.985(5) 148.9 1_554

_refine_diff_density_max         1.018
_refine_diff_density_min         -0.727
_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_Z10-Ho-14R1
_database_code_depnum_ccdc_archive 'CCDC 1506106'
_audit_update_record             
;
2017-02-28 deposited with the CCDC.
2017-03-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H15 Ho2 N3 O17'
_chemical_formula_weight         827.15

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ho Ho -0.2175 4.6783 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   9.4299(3)
_cell_length_b                   22.3272(8)
_cell_length_c                   10.0874(4)
_cell_angle_alpha                90
_cell_angle_beta                 102.8170(10)
_cell_angle_gamma                90
_cell_volume                     2070.92(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9966
_cell_measurement_theta_min      2.83
_cell_measurement_theta_max      28.28

_exptl_crystal_description       block
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.653
_exptl_crystal_F_000             1560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    7.684
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7636
_exptl_absorpt_correction_T_max  0.8476
_exptl_absorpt_process_details   'SADABS (Bruker, 2000)'

_exptl_special_details           ?

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16542
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.827
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4049
_reflns_number_gt                3586
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0125P)²+5.6246P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4049
_refine_ls_number_parameters     326
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0269
_refine_ls_R_factor_gt           0.0209
_refine_ls_wR_factor_ref         0.0430
_refine_ls_wR_factor_gt          0.0413
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ho1 Ho 1.24816(2) 0.27630(2) 1.05136(2) 0.01382(5) Uani 1 1 d . . . . .
Ho2 Ho 0.71783(2) 0.43411(2) 0.86187(2) 0.01261(5) Uani 1 1 d . . . . .
N1 N 0.5994(4) 0.41501(15) 0.6288(3) 0.0144(7) Uani 1 1 d . . . . .
N2 N 0.5330(4) 0.41311(16) 0.4068(3) 0.0175(7) Uani 1 1 d . . . . .
H2 H 0.510859 0.425731 0.325138 0.021 Uiso 1 1 d R U . . .
N3 N 0.7760(4) 0.50796(17) 0.6493(4) 0.0249(9) Uani 1 1 d . . . . .
O1 O 1.0668(3) 0.33687(14) 1.1130(3) 0.0239(7) Uani 1 1 d . . . . .
O2 O 1.0303(3) 0.28609(14) 0.8698(3) 0.0236(7) Uani 1 1 d . . . . .
O3 O 0.8276(3) 0.34113(13) 0.7975(3) 0.0227(7) Uani 1 1 d . . . . .
O4 O 0.8498(3) 0.38077(14) 1.0510(3) 0.0249(7) Uani 1 1 d . . . . .
O5 O 0.5234(3) 0.36042(13) 0.8246(3) 0.0188(6) Uani 1 1 d . . . . .
O6 O 0.3799(3) 0.29485(13) 0.6964(3) 0.0219(7) Uani 1 1 d . . . . .
O9 O 0.6017(3) 0.43635(13) 1.0526(3) 0.0208(6) Uani 1 1 d . . . . .
O7 O 0.2740(3) 0.29305(13) 0.3954(3) 0.0189(6) Uani 1 1 d . . . . .
O8 O 0.3659(3) 0.33549(13) 0.2328(3) 0.0194(6) Uani 1 1 d . . . . .
O10 O 0.4682(3) 0.49163(13) 1.1632(3) 0.0191(6) Uani 1 1 d . . . . .
O11 O 0.9748(3) 0.44747(13) 0.8704(3) 0.0211(7) Uani 1 1 d . . . . .
O12 O 1.1802(3) 0.48200(13) 1.0016(3) 0.0241(7) Uani 1 1 d . . . . .
O13 O 1.2745(3) 0.36731(14) 0.9371(3) 0.0274(7) Uani 1 1 d . . . . .
H13A H 1.242741 0.400085 0.953024 0.041 Uiso 1 1 d R U . . .
H13B H 1.344869 0.373456 0.903629 0.041 Uiso 1 1 d R U . . .
O14 O 1.5021(4) 0.28353(14) 1.0338(3) 0.0285(7) Uani 1 1 d . . . . .
H14A H 1.552260 0.294296 1.107005 0.043 Uiso 1 1 d R U . . .
H14B H 1.524105 0.304506 0.974716 0.043 Uiso 1 1 d R U . . .
O15 O 1.0826(4) 0.20924(14) 1.1127(3) 0.0292(8) Uani 1 1 d . . . . .
H15A H 0.997937 0.212121 1.070455 0.044 Uiso 1 1 d R U . . .
H15B H 1.081375 0.208491 1.193736 0.044 Uiso 1 1 d R U . . .
O16 O 0.7305(6) 0.1738(3) 0.7563(6) 0.0931(18) Uani 1 1 d . U . . .
O17 O 0.7846(5) 0.2143(2) 0.0301(5) 0.0697(14) Uani 1 1 d . . . . .
C1 C 0.4548(4) 0.36851(17) 0.4523(4) 0.0139(8) Uani 1 1 d . . . . .
C2 C 0.4981(4) 0.37054(17) 0.5928(4) 0.0131(8) Uani 1 1 d . . . . .
C3 C 0.6190(4) 0.43976(18) 0.5148(4) 0.0142(8) Uani 1 1 d . . . . .
C4 C 0.7221(4) 0.48906(19) 0.5197(4) 0.0182(9) Uani 1 1 d . . . . .
C5 C 0.7632(5) 0.5122(2) 0.4068(5) 0.0300(11) Uani 1 1 d . . . . .
H5 H 0.726220 0.496875 0.320370 0.036 Uiso 1 1 calc R U . . .
C6 C 0.8631(6) 0.5598(2) 0.4276(6) 0.0409(14) Uani 1 1 d . . . . .
H6 H 0.893773 0.577083 0.354830 0.049 Uiso 1 1 calc R U . . .
C7 C 0.9144(6) 0.5804(2) 0.5579(6) 0.0412(14) Uani 1 1 d . . . . .
H7 H 0.978480 0.612589 0.573954 0.049 Uiso 1 1 calc R U . . .
C8 C 0.8708(5) 0.5534(2) 0.6638(5) 0.0341(12) Uani 1 1 d . . . . .
H8 H 0.909376 0.567409 0.751163 0.041 Uiso 1 1 calc R U . . .
C9 C 0.3570(4) 0.32910(18) 0.3537(4) 0.0146(8) Uani 1 1 d . . . . .
C10 C 0.4631(4) 0.33827(18) 0.7092(4) 0.0139(8) Uani 1 1 d . . . . .
C11 C 0.5203(4) 0.47913(18) 1.0620(4) 0.0163(9) Uani 1 1 d . . . . .
C12 C 1.0442(5) 0.47967(18) 0.9620(4) 0.0181(9) Uani 1 1 d . . . . .
C13 C 0.9523(5) 0.34887(19) 1.0304(4) 0.0180(9) Uani 1 1 d . . . . .
C14 C 0.9342(5) 0.32279(19) 0.8855(4) 0.0190(9) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ho1 O7 2.259(3) 4_666 ?
Ho1 O6 2.324(3) 4_666 ?
Ho1 O8 2.330(3) 1_656 ?
Ho1 O15 2.343(3) . ?
Ho1 O1 2.368(3) . ?
Ho1 O13 2.376(3) . ?
Ho1 O2 2.439(3) . ?
Ho1 O14 2.445(3) . ?
Ho2 O4 2.357(3) . ?
Ho2 O10 2.386(3) 3_667 ?
Ho2 O12 2.396(3) 3_767 ?
Ho2 N1 2.406(3) . ?
Ho2 O9 2.416(3) . ?
Ho2 O11 2.424(3) . ?
Ho2 O5 2.430(3) . ?
Ho2 O3 2.470(3) . ?
Ho2 N3 2.853(4) . ?
N1 C3 1.325(5) . ?
N1 C2 1.370(5) . ?
N2 C3 1.345(5) . ?
N2 C1 1.378(5) . ?
N2 H2 0.8512 . ?
N3 C8 1.339(6) . ?
N3 C4 1.361(6) . ?
O1 C13 1.238(5) . ?
O2 C14 1.258(5) . ?
O3 C14 1.253(5) . ?
O4 C13 1.255(5) . ?
O5 C10 1.276(5) . ?
O6 C10 1.236(5) . ?
O9 C11 1.242(5) . ?
O7 C9 1.258(5) . ?
O8 C9 1.248(5) . ?
O10 C11 1.258(5) . ?
O11 C12 1.237(5) . ?
O12 C12 1.257(5) . ?
O13 H13A 0.8200 . ?
O13 H13B 0.8200 . ?
O14 H14A 0.8200 . ?
O14 H14B 0.8200 . ?
O15 H15A 0.8200 . ?
O15 H15B 0.8200 . ?
C1 C2 1.385(5) . ?
C1 C9 1.486(5) . ?
C2 C10 1.477(5) . ?
C3 C4 1.462(5) . ?
C4 C5 1.382(6) . ?
C5 C6 1.404(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.375(8) . ?
C6 H6 0.9300 . ?
C7 C8 1.367(8) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C11 C11 1.538(8) 3_667 ?
C12 C12 1.546(8) 3_767 ?
C13 C14 1.547(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O7 Ho1 O6 81.07(10) 4_666 4_666 ?
O7 Ho1 O8 146.06(11) 4_666 1_656 ?
O6 Ho1 O8 78.35(11) 4_666 1_656 ?
O7 Ho1 O15 85.83(11) 4_666 . ?
O6 Ho1 O15 72.02(11) 4_666 . ?
O8 Ho1 O15 112.59(10) 1_656 . ?
O7 Ho1 O1 140.35(10) 4_666 . ?
O6 Ho1 O1 122.77(10) 4_666 . ?
O8 Ho1 O1 73.50(10) 1_656 . ?
O15 Ho1 O1 74.54(11) . . ?
O7 Ho1 O13 102.07(11) 4_666 . ?
O6 Ho1 O13 142.28(11) 4_666 . ?
O8 Ho1 O13 79.24(11) 1_656 . ?
O15 Ho1 O13 145.29(11) . . ?
O1 Ho1 O13 78.37(11) . . ?
O7 Ho1 O2 75.03(10) 4_666 . ?
O6 Ho1 O2 141.01(11) 4_666 . ?
O8 Ho1 O2 135.58(10) 1_656 . ?
O15 Ho1 O2 75.88(11) . . ?
O1 Ho1 O2 67.00(10) . . ?
O13 Ho1 O2 73.78(11) . . ?
O7 Ho1 O14 74.68(11) 4_666 . ?
O6 Ho1 O14 72.27(11) 4_666 . ?
O8 Ho1 O14 73.49(11) 1_656 . ?
O15 Ho1 O14 141.42(11) . . ?
O1 Ho1 O14 139.19(11) . . ?
O13 Ho1 O14 72.48(10) . . ?
O2 Ho1 O14 127.93(10) . . ?
O4 Ho2 O10 132.89(10) . 3_667 ?
O4 Ho2 O12 81.79(11) . 3_767 ?
O10 Ho2 O12 73.13(10) 3_667 3_767 ?
O4 Ho2 N1 138.47(11) . . ?
O10 Ho2 N1 81.30(10) 3_667 . ?
O12 Ho2 N1 137.74(11) 3_767 . ?
O4 Ho2 O9 67.46(10) . . ?
O10 Ho2 O9 67.52(9) 3_667 . ?
O12 Ho2 O9 73.80(10) 3_767 . ?
N1 Ho2 O9 126.00(11) . . ?
O4 Ho2 O11 71.90(11) . . ?
O10 Ho2 O11 128.61(10) 3_667 . ?
O12 Ho2 O11 67.22(9) 3_767 . ?
N1 Ho2 O11 107.46(11) . . ?
O9 Ho2 O11 126.52(10) . . ?
O4 Ho2 O5 91.58(11) . . ?
O10 Ho2 O5 86.69(10) 3_667 . ?
O12 Ho2 O5 144.19(10) 3_767 . ?
N1 Ho2 O5 63.79(10) . . ?
O9 Ho2 O5 71.18(10) . . ?
O11 Ho2 O5 143.40(10) . . ?
O4 Ho2 O3 67.12(10) . . ?
O10 Ho2 O3 153.80(10) 3_667 . ?
O12 Ho2 O3 132.05(10) 3_767 . ?
N1 Ho2 O3 74.04(10) . . ?
O9 Ho2 O3 121.13(10) . . ?
O11 Ho2 O3 68.82(10) . . ?
O5 Ho2 O3 74.70(10) . . ?
O4 Ho2 N3 138.22(11) . . ?
O10 Ho2 N3 77.18(10) 3_667 . ?
O12 Ho2 N3 81.99(11) 3_767 . ?
N1 Ho2 N3 59.54(11) . . ?
O9 Ho2 N3 141.55(10) . . ?
O11 Ho2 N3 66.32(10) . . ?
O5 Ho2 N3 122.64(10) . . ?
O3 Ho2 N3 97.28(11) . . ?
C3 N1 C2 107.2(3) . . ?
C3 N1 Ho2 130.6(3) . . ?
C2 N1 Ho2 122.2(2) . . ?
C3 N2 C1 108.7(3) . . ?
C3 N2 H2 127.7 . . ?
C1 N2 H2 121.8 . . ?
C8 N3 C4 116.0(4) . . ?
C8 N3 Ho2 126.2(3) . . ?
C4 N3 Ho2 116.7(3) . . ?
C13 O1 Ho1 121.3(3) . . ?
C14 O2 Ho1 118.3(3) . . ?
C14 O3 Ho2 113.9(3) . . ?
C13 O4 Ho2 116.1(3) . . ?
C10 O5 Ho2 124.8(2) . . ?
C10 O6 Ho1 147.2(3) . 4_465 ?
C11 O9 Ho2 118.2(3) . . ?
C9 O7 Ho1 147.4(3) . 4_465 ?
C9 O8 Ho1 125.3(3) . 1_454 ?
C11 O10 Ho2 118.6(3) . 3_667 ?
C12 O11 Ho2 117.2(3) . . ?
C12 O12 Ho2 117.8(3) . 3_767 ?
Ho1 O13 H13A 125.9 . . ?
Ho1 O13 H13B 121.6 . . ?
H13A O13 H13B 107.2 . . ?
Ho1 O14 H14A 109.4 . . ?
Ho1 O14 H14B 120.0 . . ?
H14A O14 H14B 107.4 . . ?
Ho1 O15 H15A 116.2 . . ?
Ho1 O15 H15B 115.7 . . ?
H15A O15 H15B 107.0 . . ?
N2 C1 C2 105.0(3) . . ?
N2 C1 C9 120.2(3) . . ?
C2 C1 C9 134.7(4) . . ?
N1 C2 C1 109.0(3) . . ?
N1 C2 C10 114.1(3) . . ?
C1 C2 C10 136.9(4) . . ?
N1 C3 N2 110.1(4) . . ?
N1 C3 C4 120.3(4) . . ?
N2 C3 C4 129.6(4) . . ?
N3 C4 C5 124.2(4) . . ?
N3 C4 C3 111.7(4) . . ?
C5 C4 C3 124.1(4) . . ?
C4 C5 C6 117.5(5) . . ?
C4 C5 H5 121.2 . . ?
C6 C5 H5 121.2 . . ?
C7 C6 C5 118.5(5) . . ?
C7 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
C8 C7 C6 119.8(5) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
N3 C8 C7 124.0(5) . . ?
N3 C8 H8 118.0 . . ?
C7 C8 H8 118.0 . . ?
O8 C9 O7 125.5(4) . . ?
O8 C9 C1 114.8(4) . . ?
O7 C9 C1 119.6(3) . . ?
O6 C10 O5 122.9(4) . . ?
O6 C10 C2 123.2(4) . . ?
O5 C10 C2 113.8(3) . . ?
O9 C11 O10 126.2(4) . . ?
O9 C11 C11 116.8(5) . 3_667 ?
O10 C11 C11 117.0(5) . 3_667 ?
O11 C12 O12 126.5(4) . . ?
O11 C12 C12 117.2(5) . 3_767 ?
O12 C12 C12 116.3(5) . 3_767 ?
O1 C13 O4 126.9(4) . . ?
O1 C13 C14 116.8(4) . . ?
O4 C13 C14 116.2(4) . . ?
O3 C14 O2 127.6(4) . . ?
O3 C14 C13 116.7(4) . . ?
O2 C14 C13 115.6(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
N2 H2 O10 0.85 2.17 2.969(4) 156.6 1_554
O13 H13A O12 0.82 2.02 2.834(4) 175.5 .
O13 H13B O5 0.82 2.04 2.828(4) 162.1 1_655
O14 H14A O16 0.82 2.12 2.905(7) 161.5 4_666
O14 H14B O5 0.82 1.96 2.762(4) 165.1 1_655
O15 H15A O17 0.82 1.96 2.750(6) 160.9 1_556
O15 H15B O2 0.82 1.94 2.747(4) 166.0 4_566

_refine_diff_density_max         1.009
_refine_diff_density_min         -0.561
_refine_diff_density_rms         0.123

