# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_1sm
_database_code_depnum_ccdc_archive 'CCDC 1863664'
_audit_update_record             
;
2018-08-24 deposited with the CCDC.
2018-09-26 downloaded from the CCDC.
;
_audit_creation_date             2018-03-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H7 O8 Sm, C4 H3 O2, H2 O'
_chemical_formula_sum            'C10 H12 O11 Sm'
_chemical_formula_weight         458.55
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sm Sm -0.1638 3.4418 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.0814(7)
_cell_length_b                   9.3267(7)
_cell_length_c                   9.8315(7)
_cell_angle_alpha                83.997(3)
_cell_angle_beta                 65.410(2)
_cell_angle_gamma                63.057(2)
_cell_volume                     671.38(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2015
_cell_measurement_temperature    296
_cell_measurement_theta_max      28.321
_cell_measurement_theta_min      2.949
_shelx_estimated_absorpt_T_max   0.666
_shelx_estimated_absorpt_T_min   0.471
_exptl_absorpt_coefficient_mu    4.433
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6769
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0656 before and 0.0554 after correction. The Ratio of minimum to maximum transmission is 0.9077. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.268
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0514
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            32296
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.321
_diffrn_reflns_theta_min         2.949
_diffrn_ambient_temperature      296.0
_diffrn_detector                 'Bruker PHOTON 100 area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'PHOTON area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'four-circle KAPPA diffractometer'
_diffrn_measurement_device_type  'BRUKER D8 QUEST CMOS'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    '0.5 mm'
_diffrn_radiation_monochromator  'graphiteDouble Bounce Multilayer Mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed x-ray tube'
_diffrn_source_type              'Incoatec I\mus'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3078
_reflns_number_total             3330
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2016)'
_computing_data_collection       'APEX 3 (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'

_refine_diff_density_max         0.465
_refine_diff_density_min         -0.383
_refine_diff_density_rms         0.100
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3330
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0221
_refine_ls_R_factor_gt           0.0176
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0145P)²+0.3989P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0348
_refine_ls_wR_factor_ref         0.0359
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 O11-H11B = O11-H11A
 0.84 with sigma of 0.01
 O7-H7B = O7-H7A
 0.84 with sigma of 0.01
 O10-H10
 0.82 with sigma of 0.01
 H7B-H7A
 1.42 with sigma of 0.02
 H11A-H11B
 1.37 with sigma of 0.02
 O8-H8A = O8-H8B
 0.84 with sigma of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C9(H9), C10(H10A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.23509(2) 0.50942(2) 0.53887(2) 0.01134(4) Uani 1 1 d . . . . .
O1 O 0.4624(2) 0.41883(19) 0.26436(18) 0.0178(3) Uani 1 1 d . . . . .
O2 O 0.2071(2) 0.63720(19) 0.30437(17) 0.0173(3) Uani 1 1 d . . . . .
O3 O 0.4208(2) 0.65085(18) 0.47193(19) 0.0205(4) Uani 1 1 d . . . . .
O4 O 0.6001(2) 0.7658(2) 0.4034(2) 0.0252(4) Uani 1 1 d . . . . .
O5 O 0.0217(2) 1.21461(19) 0.38833(19) 0.0185(3) Uani 1 1 d . . . . .
O6 O 0.1423(2) 1.34928(18) 0.43908(19) 0.0206(4) Uani 1 1 d . . . . .
O7 O 0.0141(2) 0.4566(2) 0.7596(2) 0.0212(4) Uani 1 1 d D . . . .
H7A H -0.054(3) 0.434(3) 0.740(3) 0.036(9) Uiso 1 1 d D . . . .
H7B H 0.053(4) 0.392(3) 0.817(3) 0.036(9) Uiso 1 1 d D . . . .
O8 O 0.2156(2) 0.5976(3) 0.7725(2) 0.0300(4) Uani 1 1 d D . . . .
H8A H 0.299(3) 0.611(4) 0.774(4) 0.042(10) Uiso 1 1 d D . . . .
H8B H 0.125(3) 0.641(4) 0.853(2) 0.059(12) Uiso 1 1 d D . . . .
C1 C 0.3629(3) 0.5337(3) 0.2153(2) 0.0145(4) Uani 1 1 d . . . . .
C2 C 0.4209(3) 0.5506(3) 0.0515(3) 0.0187(5) Uani 1 1 d . . . . .
H2 H 0.341803 0.636564 0.020099 0.022 Uiso 1 1 calc R . . . .
C3 C 0.4487(3) 0.7731(3) 0.4335(3) 0.0148(4) Uani 1 1 d . . . . .
C4 C 0.2966(3) 0.9250(3) 0.4267(3) 0.0158(5) Uani 1 1 d . . . . .
H4 H 0.191734 0.922178 0.436278 0.019 Uiso 1 1 calc R . . . .
C5 C 0.3045(3) 1.0636(3) 0.4078(3) 0.0147(4) Uani 1 1 d . . . . .
H5 H 0.412162 1.065198 0.391646 0.018 Uiso 1 1 calc R . . . .
C6 C 0.1474(3) 1.2180(3) 0.4113(2) 0.0142(4) Uani 1 1 d . . . . .
O9 O 0.0718(2) 0.2194(2) 0.9545(2) 0.0270(4) Uani 1 1 d . . . . .
O10 O 0.2232(3) -0.0302(2) 0.8380(3) 0.0383(5) Uani 1 1 d D . . . .
H10 H 0.135(3) -0.004(4) 0.819(4) 0.057(12) Uiso 1 1 d D . . . .
C7 C 0.2041(3) 0.0855(3) 0.9175(3) 0.0223(5) Uani 1 1 d . . . . .
C8 C 0.3580(3) 0.0409(3) 0.9598(3) 0.0193(5) Uani 1 1 d . . . . .
C9 C 0.3634(3) 0.1582(3) 1.0304(3) 0.0230(5) Uani 1 1 d . . . . .
H9 H 0.272132 0.264193 1.050302 0.028 Uiso 1 1 calc R . . . .
C10 C 0.5052(3) 0.1173(3) 1.0713(3) 0.0229(5) Uani 1 1 d . . . . .
H10A H 0.508731 0.195504 1.119516 0.027 Uiso 1 1 calc R . . . .
O11 O -0.0509(3) 0.0391(2) 0.7778(2) 0.0301(4) Uani 1 1 d D . . . .
H11A H -0.101(5) 0.128(2) 0.749(4) 0.062(12) Uiso 1 1 d D . . . .
H11B H -0.046(5) -0.033(3) 0.731(4) 0.059(12) Uiso 1 1 d 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 O1 2.5531(16) . ?
Sm1 O2 2.5374(15) . ?
Sm1 O3 2.4349(16) . ?
Sm1 O3 2.7448(17) 2_666 ?
Sm1 O4 2.4641(16) 2_666 ?
Sm1 O5 2.4765(15) 2_576 ?
Sm1 O6 2.4575(16) 1_545 ?
Sm1 O7 2.4552(17) . ?
Sm1 O8 2.4311(18) . ?
O1 C1 1.255(3) . ?
O2 C1 1.268(3) . ?
O3 C3 1.264(3) . ?
O4 C3 1.250(3) . ?
O5 C6 1.266(3) . ?
O6 C6 1.259(3) . ?
O7 H7A 0.834(10) . ?
O7 H7B 0.838(10) . ?
O8 H8A 0.826(10) . ?
O8 H8B 0.829(10) . ?
C1 C2 1.488(3) . ?
C2 C2 1.319(5) 2_665 ?
C2 H2 0.9300 . ?
C3 C4 1.484(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.317(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.489(3) . ?
O9 C7 1.228(3) . ?
O10 H10 0.818(10) . ?
O10 C7 1.304(3) . ?
C7 C8 1.490(3) . ?
C8 C9 1.385(3) . ?
C8 C10 1.389(3) 2_657 ?
C9 H9 0.9300 . ?
C9 C10 1.385(3) . ?
C10 H10A 0.9300 . ?
O11 H11A 0.835(10) . ?
O11 H11B 0.835(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Sm1 O3 71.40(5) . 2_666 ?
O2 Sm1 O1 51.03(5) . . ?
O2 Sm1 O3 116.53(5) . 2_666 ?
O3 Sm1 O1 71.65(5) . . ?
O3 Sm1 O2 76.23(5) . . ?
O3 Sm1 O3 60.89(6) . 2_666 ?
O3 Sm1 O4 110.06(5) . 2_666 ?
O3 Sm1 O5 84.05(5) . 2_576 ?
O3 Sm1 O6 144.67(6) . 1_545 ?
O3 Sm1 O7 140.80(6) . . ?
O4 Sm1 O1 87.87(6) 2_666 . ?
O4 Sm1 O2 135.38(6) 2_666 . ?
O4 Sm1 O3 49.22(5) 2_666 2_666 ?
O4 Sm1 O5 151.80(6) 2_666 2_576 ?
O5 Sm1 O1 120.15(5) 2_576 . ?
O5 Sm1 O2 70.62(5) 2_576 . ?
O5 Sm1 O3 138.55(5) 2_576 2_666 ?
O6 Sm1 O1 74.20(5) 1_545 . ?
O6 Sm1 O2 75.48(5) 1_545 . ?
O6 Sm1 O3 115.55(5) 1_545 2_666 ?
O6 Sm1 O4 77.14(5) 1_545 2_666 ?
O6 Sm1 O5 105.83(5) 1_545 2_576 ?
O7 Sm1 O1 146.23(6) . . ?
O7 Sm1 O2 130.21(5) . . ?
O7 Sm1 O3 112.02(5) . 2_666 ?
O7 Sm1 O4 73.11(6) . 2_666 ?
O7 Sm1 O5 80.63(6) . 2_576 ?
O7 Sm1 O6 74.48(6) . 1_545 ?
O8 Sm1 O1 139.03(6) . . ?
O8 Sm1 O2 136.12(6) . . ?
O8 Sm1 O3 73.12(6) . . ?
O8 Sm1 O3 73.60(6) . 2_666 ?
O8 Sm1 O4 85.10(7) . 2_666 ?
O8 Sm1 O5 75.61(6) . 2_576 ?
O8 Sm1 O6 141.94(6) . 1_545 ?
O8 Sm1 O7 68.19(6) . . ?
C1 O1 Sm1 93.94(13) . . ?
C1 O2 Sm1 94.32(13) . . ?
Sm1 O3 Sm1 119.11(6) . 2_666 ?
C3 O3 Sm1 152.74(15) . . ?
C3 O3 Sm1 88.14(13) . 2_666 ?
C3 O4 Sm1 101.92(14) . 2_666 ?
C6 O5 Sm1 107.41(13) . 2_576 ?
C6 O6 Sm1 152.32(15) . 1_565 ?
Sm1 O7 H7A 114(2) . . ?
Sm1 O7 H7B 118(2) . . ?
H7A O7 H7B 110(2) . . ?
Sm1 O8 H8A 121(2) . . ?
Sm1 O8 H8B 130(3) . . ?
H8A O8 H8B 108(3) . . ?
O1 C1 O2 120.7(2) . . ?
O1 C1 C2 121.4(2) . . ?
O2 C1 C2 117.9(2) . . ?
C1 C2 H2 118.4 . . ?
C2 C2 C1 123.2(3) 2_665 . ?
C2 C2 H2 118.4 2_665 . ?
O3 C3 Sm1 66.81(12) . 2_666 ?
O3 C3 C4 118.2(2) . . ?
O4 C3 Sm1 53.88(11) . 2_666 ?
O4 C3 O3 120.6(2) . . ?
O4 C3 C4 121.2(2) . . ?
C4 C3 Sm1 173.64(16) . 2_666 ?
C3 C4 H4 118.7 . . ?
C5 C4 C3 122.5(2) . . ?
C5 C4 H4 118.7 . . ?
C4 C5 H5 118.8 . . ?
C4 C5 C6 122.5(2) . . ?
C6 C5 H5 118.8 . . ?
O5 C6 C5 119.73(19) . . ?
O6 C6 O5 121.6(2) . . ?
O6 C6 C5 118.7(2) . . ?
C7 O10 H10 112(3) . . ?
O9 C7 O10 123.4(2) . . ?
O9 C7 C8 122.7(2) . . ?
O10 C7 C8 113.9(2) . . ?
C9 C8 C7 119.5(2) . . ?
C9 C8 C10 120.3(2) . 2_657 ?
C10 C8 C7 120.3(2) 2_657 . ?
C8 C9 H9 120.1 . . ?
C10 C9 C8 119.8(2) . . ?
C10 C9 H9 120.1 . . ?
C8 C10 H10A 120.0 2_657 . ?
C9 C10 C8 119.9(2) . 2_657 ?
C9 C10 H10A 120.0 . . ?
H11A O11 H11B 110(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
O7 H7A O2 0.834(10) 1.988(10) 2.821(2) 176(3) 2_566
O7 H7B O9 0.838(10) 1.987(15) 2.781(2) 158(3) .
O8 H8A O1 0.826(10) 1.928(14) 2.726(2) 162(3) 2_666
O8 H8B O9 0.829(10) 2.016(13) 2.832(3) 168(4) 2_567
O10 H10 O11 0.818(10) 1.762(11) 2.579(3) 176(4) .
O11 H11A O2 0.835(10) 2.062(11) 2.889(3) 171(3) 2_566
O11 H11B O5 0.835(10) 2.033(10) 2.867(3) 177(4) 2_566

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
Sm1 O1 C1 O2 -1.1(2) . . . . ?
Sm1 O1 C1 C2 -179.39(19) . . . . ?
Sm1 O2 C1 O1 1.1(2) . . . . ?
Sm1 O2 C1 C2 179.45(17) . . . . ?
Sm1 O3 C3 Sm1 -179.0(3) . . . 2_666 ?
Sm1 O3 C3 O4 3.7(2) 2_666 . . . ?
Sm1 O3 C3 O4 -175.3(2) . . . . ?
Sm1 O3 C3 C4 5.4(5) . . . . ?
Sm1 O3 C3 C4 -175.64(19) 2_666 . . . ?
Sm1 O4 C3 O3 -4.2(3) 2_666 . . . ?
Sm1 O4 C3 C4 175.11(18) 2_666 . . . ?
Sm1 O5 C6 O6 -11.6(3) 2_576 . . . ?
Sm1 O5 C6 C5 167.56(16) 2_576 . . . ?
Sm1 O6 C6 O5 159.7(2) 1_565 . . . ?
Sm1 O6 C6 C5 -19.4(4) 1_565 . . . ?
O1 C1 C2 C2 -1.1(4) . . . 2_665 ?
O2 C1 C2 C2 -179.4(3) . . . 2_665 ?
O3 C3 C4 C5 170.7(2) . . . . ?
O4 C3 C4 C5 -8.7(4) . . . . ?
C3 C4 C5 C6 -175.8(2) . . . . ?
C4 C5 C6 O5 -20.9(3) . . . . ?
C4 C5 C6 O6 158.2(2) . . . . ?
O9 C7 C8 C9 -6.8(4) . . . . ?
O9 C7 C8 C10 173.2(2) . . . 2_657 ?
O10 C7 C8 C9 173.2(2) . . . . ?
O10 C7 C8 C10 -6.9(4) . . . 2_657 ?
C7 C8 C9 C10 179.4(2) . . . . ?
C8 C9 C10 C8 0.6(4) . . . 2_657 ?
C10 C8 C9 C10 -0.6(4) 2_657 . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_14dy
_database_code_depnum_ccdc_archive 'CCDC 1863677'
_audit_update_record             
;
2018-08-24 deposited with the CCDC.
2018-09-26 downloaded from the CCDC.
;
_audit_creation_date             2018-08-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C9 H8 Dy O8, 0.7(H2 O1)'
_chemical_formula_sum            'C9 H9.40 Dy O8.70'
_chemical_formula_weight         419.27
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Dy Dy -0.1892 4.4098 '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'

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

_cell_length_a                   8.2905(3)
_cell_length_b                   18.7105(7)
_cell_length_c                   7.7970(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.9687(15)
_cell_angle_gamma                90.00
_cell_volume                     1162.79(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4077
_cell_measurement_temperature    296.0
_cell_measurement_theta_max      26.742
_cell_measurement_theta_min      2.928
_exptl_absorpt_coefficient_mu    6.464
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5938
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0611 before and 0.0328 after correction. The Ratio of minimum to maximum transmission is 0.7966. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            'light orange'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    2.395
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             796
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6131
_diffrn_reflns_theta_full        26.74
_diffrn_reflns_theta_max         26.74
_diffrn_reflns_theta_min         2.93
_diffrn_ambient_temperature      296.0
_diffrn_detector                 'Bruker PHOTON 100 area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'PHOTON area detector'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'four-circle KAPPA diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_collimation    '0.5 mm'
_diffrn_radiation_monochromator  'graphiteDouble Bounce Multilayer Mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed x-ray tube'
_diffrn_source_type              'Incoatec I\mus'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                2230
_reflns_number_total             2461
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.667
_refine_diff_density_min         -0.510
_refine_diff_density_rms         0.111
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2461
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0227
_refine_ls_R_factor_gt           0.0188
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0207P)²+0.6290P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0427
_refine_ls_wR_factor_ref         0.0441
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 O9-H9A = O9-H9B
 0.85 with sigma of 0.02
 O7-H7A = O7-H7B = O8-H8A
 0.84 with sigma of 0.01
 O8-H8B
 0.84 with sigma of 0.01
 H9A-H9B
 1.34 with sigma of 0.04
3. Others
 Fixed Sof: O9(0.7) H9A(0.7) H9B(0.7)
4.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Dy1 Dy 0.243261(15) 0.519761(7) 0.761177(16) 0.01374(6) Uani 1 d . . .
O1 O 0.1678(3) 0.44522(11) 0.5228(3) 0.0260(5) Uani 1 d . . .
O2 O -0.0213(3) 0.39913(11) 0.2901(3) 0.0257(5) Uani 1 d . . .
O3 O 0.6031(3) 0.12153(11) 0.6249(3) 0.0249(5) Uani 1 d . . .
O4 O 0.3851(3) 0.07105(11) 0.4338(3) 0.0268(5) Uani 1 d . . .
O5 O 0.1980(2) 0.53944(11) 1.0515(3) 0.0224(5) Uani 1 d . . .
O6 O 0.0016(3) 0.54384(11) 1.1980(3) 0.0198(4) Uani 1 d . . .
O7 O 0.2496(3) 0.59351(14) 0.5003(3) 0.0316(5) Uani 1 d . . D
O8 O 0.5105(3) 0.50475(16) 0.6873(3) 0.0319(6) Uani 1 d . . D
C1 C 0.2079(4) 0.32672(15) 0.4358(4) 0.0188(6) Uani 1 d . . .
C2 C 0.3696(4) 0.32151(16) 0.5467(4) 0.0236(7) Uani 1 d . . .
H2 H 0.4238 0.3621 0.6036 0.028 Uiso 1 calc . . R
C3 C 0.4505(4) 0.25623(16) 0.5731(4) 0.0227(7) Uani 1 d . . .
H3 H 0.5596 0.2532 0.6468 0.027 Uiso 1 calc . . R
C4 C 0.3704(4) 0.19521(15) 0.4905(4) 0.0190(6) Uani 1 d . . .
C5 C 0.2096(4) 0.20032(16) 0.3790(4) 0.0271(7) Uani 1 d . . .
H5 H 0.1555 0.1597 0.3226 0.033 Uiso 1 calc . . R
C6 C 0.1287(4) 0.26546(17) 0.3510(5) 0.0283(7) Uani 1 d . . .
H6 H 0.0207 0.2686 0.2749 0.034 Uiso 1 calc . . R
C7 C 0.1119(4) 0.39541(15) 0.4145(4) 0.0177(6) Uani 1 d . . .
C8 C 0.4587(4) 0.12416(14) 0.5178(4) 0.0174(6) Uani 1 d . . .
C9 C 0.0583(4) 0.52415(15) 1.0718(4) 0.0172(6) Uani 1 d . . .
O9 O 0.2082(6) 0.7605(3) 0.5295(8) 0.0745(15) Uani 0.70 d . . D
H9A H 0.193(10) 0.800(3) 0.573(10) 0.112 Uiso 0.70 d . . DR
H9B H 0.133(8) 0.753(4) 0.433(7) 0.112 Uiso 0.70 d . . DR
H7A H 0.250(6) 0.6382(6) 0.508(7) 0.076(17) Uiso 1 d . . D
H7B H 0.176(4) 0.584(2) 0.404(3) 0.052(13) Uiso 1 d . . D
H8A H 0.598(3) 0.489(2) 0.758(5) 0.061(15) Uiso 1 d . . D
H8B H 0.553(7) 0.529(3) 0.620(6) 0.11(2) Uiso 1 d . . D


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Dy1 O1 2.270(2) . ?
Dy1 O2 2.333(2) 3_566 ?
Dy1 O3 2.327(2) 2_656 ?
Dy1 O4 2.283(2) 4_566 ?
Dy1 O5 2.422(2) . ?
Dy1 O6 2.448(2) 3_567 ?
Dy1 O7 2.471(2) . ?
Dy1 O8 2.454(2) . ?
O1 C7 1.257(3) . ?
O2 Dy1 2.333(2) 3_566 ?
O2 C7 1.256(3) . ?
O3 Dy1 2.327(2) 2_646 ?
O3 C8 1.258(3) . ?
O4 Dy1 2.283(2) 4_565 ?
O4 C8 1.253(3) . ?
O5 C9 1.245(3) . ?
O6 Dy1 2.448(2) 3_567 ?
O6 C9 1.256(4) . ?
O7 H7A 0.838(10) . ?
O7 H7B 0.843(10) . ?
O8 H8A 0.836(10) . ?
O8 H8B 0.837(10) . ?
C1 C2 1.384(4) . ?
C1 C6 1.394(4) . ?
C1 C7 1.497(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.382(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.387(4) . ?
C4 C5 1.380(4) . ?
C4 C8 1.505(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.379(4) . ?
C6 H6 0.9300 . ?
C9 C9 1.552(6) 3_567 ?
O9 H9A 0.84(2) . ?
O9 H9B 0.84(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Dy1 O2 103.47(7) . 3_566 ?
O1 Dy1 O3 144.49(8) . 2_656 ?
O1 Dy1 O4 90.37(8) . 4_566 ?
O1 Dy1 O5 141.26(7) . . ?
O1 Dy1 O6 75.89(7) . 3_567 ?
O1 Dy1 O7 74.48(8) . . ?
O1 Dy1 O8 78.50(8) . . ?
O2 Dy1 O5 75.15(7) 3_566 . ?
O2 Dy1 O6 72.27(7) 3_566 3_567 ?
O2 Dy1 O7 71.95(8) 3_566 . ?
O2 Dy1 O8 138.99(9) 3_566 . ?
O3 Dy1 O2 81.73(7) 2_656 3_566 ?
O3 Dy1 O5 74.23(7) 2_656 . ?
O3 Dy1 O6 137.27(7) 2_656 3_567 ?
O3 Dy1 O7 73.97(8) 2_656 . ?
O3 Dy1 O8 75.43(9) 2_656 . ?
O4 Dy1 O2 147.06(8) 4_566 3_566 ?
O4 Dy1 O3 104.18(8) 4_566 2_656 ?
O4 Dy1 O5 75.48(8) 4_566 . ?
O4 Dy1 O6 82.69(7) 4_566 3_567 ?
O4 Dy1 O7 140.99(9) 4_566 . ?
O4 Dy1 O8 72.62(9) 4_566 . ?
O5 Dy1 O6 66.75(7) . 3_567 ?
O5 Dy1 O7 136.76(8) . . ?
O5 Dy1 O8 128.22(8) . . ?
O6 Dy1 O7 125.78(8) 3_567 . ?
O6 Dy1 O8 144.03(7) 3_567 . ?
O8 Dy1 O7 69.24(9) . . ?
C7 O1 Dy1 166.7(2) . . ?
C7 O2 Dy1 130.77(18) . 3_566 ?
C8 O3 Dy1 127.32(18) . 2_646 ?
C8 O4 Dy1 175.4(2) . 4_565 ?
C9 O5 Dy1 118.21(18) . . ?
C9 O6 Dy1 117.47(18) . 3_567 ?
Dy1 O7 H7A 120(3) . . ?
Dy1 O7 H7B 116(3) . . ?
H7A O7 H7B 105(4) . . ?
Dy1 O8 H8A 124(3) . . ?
Dy1 O8 H8B 130(4) . . ?
H8A O8 H8B 99(5) . . ?
C2 C1 C6 119.2(3) . . ?
C2 C1 C7 121.6(3) . . ?
C6 C1 C7 119.1(3) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.2(3) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.5(3) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C8 120.6(3) . . ?
C5 C4 C3 119.5(3) . . ?
C5 C4 C8 119.9(3) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.3(3) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 H6 119.8 . . ?
C5 C6 C1 120.4(3) . . ?
C5 C6 H6 119.8 . . ?
O1 C7 C1 118.4(3) . . ?
O2 C7 O1 124.2(3) . . ?
O2 C7 C1 117.5(2) . . ?
O3 C8 C4 117.8(2) . . ?
O4 C8 O3 123.6(3) . . ?
O4 C8 C4 118.6(3) . . ?
O5 C9 O6 126.4(3) . . ?
O5 C9 C9 117.3(3) . 3_567 ?
O6 C9 C9 116.3(3) . 3_567 ?
H9A O9 H9B 110(5) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O7 H7A O9 0.838(10) 2.329(14) 3.159(6) 171(5) .
O7 H7B O6 0.843(10) 1.993(13) 2.825(3) 169(4) 1_554
O8 H8A O5 0.836(10) 1.990(12) 2.822(3) 173(4) 3_667

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
Dy1 O1 C7 O2 101.5(9) . . . . ?
Dy1 O1 C7 C1 -77.5(9) . . . . ?
Dy1 O2 C7 O1 -14.8(4) 3_566 . . . ?
Dy1 O2 C7 C1 164.22(18) 3_566 . . . ?
Dy1 O3 C8 O4 -11.6(4) 2_646 . . . ?
Dy1 O3 C8 C4 168.20(18) 2_646 . . . ?
Dy1 O4 C8 O3 -140(2) 4_565 . . . ?
Dy1 O4 C8 C4 40(3) 4_565 . . . ?
Dy1 O5 C9 O6 -164.4(2) . . . . ?
Dy1 O5 C9 C9 15.8(4) . . . 3_567 ?
Dy1 O6 C9 O5 -164.6(2) 3_567 . . . ?
Dy1 O6 C9 C9 15.3(4) 3_567 . . 3_567 ?
O1 Dy1 O5 C9 -33.1(3) . . . . ?
O2 Dy1 O1 C7 -93.2(9) 3_566 . . . ?
O2 Dy1 O5 C9 60.1(2) 3_566 . . . ?
O3 Dy1 O1 C7 172.1(8) 2_656 . . . ?
O3 Dy1 O5 C9 145.5(2) 2_656 . . . ?
O4 Dy1 O1 C7 56.6(9) 4_566 . . . ?
O4 Dy1 O5 C9 -104.9(2) 4_566 . . . ?
O5 Dy1 O1 C7 -10.3(9) . . . . ?
O6 Dy1 O1 C7 -25.8(9) 3_567 . . . ?
O6 Dy1 O5 C9 -16.70(19) 3_567 . . . ?
O7 Dy1 O1 C7 -159.8(9) . . . . ?
O7 Dy1 O5 C9 101.5(2) . . . . ?
O8 Dy1 O1 C7 128.8(9) . . . . ?
O8 Dy1 O5 C9 -158.2(2) . . . . ?
C1 C2 C3 C4 -0.7(5) . . . . ?
C2 C1 C6 C5 0.9(5) . . . . ?
C2 C1 C7 O1 -12.7(4) . . . . ?
C2 C1 C7 O2 168.2(3) . . . . ?
C2 C3 C4 C5 1.0(5) . . . . ?
C2 C3 C4 C8 179.5(3) . . . . ?
C3 C4 C5 C6 -0.5(5) . . . . ?
C3 C4 C8 O3 3.8(4) . . . . ?
C3 C4 C8 O4 -176.4(3) . . . . ?
C4 C5 C6 C1 -0.5(5) . . . . ?
C5 C4 C8 O3 -177.8(3) . . . . ?
C5 C4 C8 O4 2.0(4) . . . . ?
C6 C1 C2 C3 -0.3(5) . . . . ?
C6 C1 C7 O1 163.0(3) . . . . ?
C6 C1 C7 O2 -16.1(4) . . . . ?
C7 C1 C2 C3 175.5(3) . . . . ?
C7 C1 C6 C5 -175.0(3) . . . . ?
C8 C4 C5 C6 -178.9(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_13tb
_database_code_depnum_ccdc_archive 'CCDC 1863676'
_audit_update_record             
;
2018-08-24 deposited with the CCDC.
2018-09-26 downloaded from the CCDC.
;
_audit_creation_date             2018-08-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C9 H8 O8 Tb, 0.7(H2 O1)'
_chemical_formula_sum            'C9 H9.40 O8.70 Tb'
_chemical_formula_weight         415.69
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   8.3156(4)
_cell_length_b                   18.7115(7)
_cell_length_c                   7.8028(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.171(2)
_cell_angle_gamma                90.00
_cell_volume                     1166.06(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3951
_cell_measurement_temperature    296.0
_cell_measurement_theta_max      27.12
_cell_measurement_theta_min      2.93
_exptl_absorpt_coefficient_mu    6.103
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5747
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1997 before and 0.0517 after correction. The Ratio of minimum to maximum transmission is 0.7262. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            'light orange'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    2.368
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0607
_diffrn_reflns_av_unetI/netI     0.0539
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            12626
_diffrn_reflns_theta_full        28.32
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         2.93
_diffrn_ambient_temperature      296.0
_diffrn_detector                 'Bruker PHOTON 100 area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'PHOTON area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'four-circle KAPPA diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_collimation    '0.5 mm'
_diffrn_radiation_monochromator  'graphiteDouble Bounce Multilayer Mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed x-ray tube'
_diffrn_source_target            Cu
_diffrn_source_type              'Incoatec I\mus'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                2288
_reflns_number_total             2891
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.932
_refine_diff_density_min         -0.901
_refine_diff_density_rms         0.183
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2891
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0311
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0204P)²+0.6562P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0526
_refine_ls_wR_factor_ref         0.0568
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 O9-H9A = O9-H9B
 0.85 with sigma of 0.02
 O7-H7A = O7-H7B = O8-H8A
 0.84 with sigma of 0.01
 O8-H8B
 0.84 with sigma of 0.01
 H9A-H9B
 1.34 with sigma of 0.04
3. Others
 Fixed Sof: O9(0.7) H9A(0.7) H9B(0.7)
4.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Tb1 Tb 0.24340(2) 0.519787(10) 0.76126(3) 0.01250(7) Uani 1 d . . .
O1 O 0.1679(4) 0.44524(16) 0.5214(4) 0.0246(7) Uani 1 d . . .
O2 O -0.0210(3) 0.39888(16) 0.2886(4) 0.0241(7) Uani 1 d . . .
O3 O 0.6039(4) 0.12249(16) 0.6245(4) 0.0234(7) Uani 1 d . . .
O4 O 0.3865(4) 0.07155(15) 0.4332(4) 0.0248(7) Uani 1 d . . .
O5 O 0.1981(3) 0.53927(16) 1.0525(4) 0.0216(7) Uani 1 d . . .
O6 O 0.0021(3) 0.54418(15) 1.1977(4) 0.0180(6) Uani 1 d . . .
O7 O 0.2486(4) 0.5942(2) 0.5004(5) 0.0295(8) Uani 1 d . . D
O8 O 0.5113(4) 0.5051(2) 0.6869(5) 0.0289(8) Uani 1 d . . D
C1 C 0.2078(5) 0.3265(2) 0.4339(6) 0.0172(9) Uani 1 d . . .
C2 C 0.3698(5) 0.3217(2) 0.5464(6) 0.0227(10) Uani 1 d . . .
H2 H 0.4239 0.3622 0.6035 0.027 Uiso 1 calc . . R
C3 C 0.4495(5) 0.2566(2) 0.5727(6) 0.0228(10) Uani 1 d . . .
H3 H 0.5582 0.2537 0.6471 0.027 Uiso 1 calc . . R
C4 C 0.3714(5) 0.1954(2) 0.4909(6) 0.0176(9) Uani 1 d . . .
C5 C 0.2092(6) 0.2007(2) 0.3783(7) 0.0259(11) Uani 1 d . . .
H5 H 0.1548 0.1601 0.3221 0.031 Uiso 1 calc . . R
C6 C 0.1299(6) 0.2654(2) 0.3501(6) 0.0254(11) Uani 1 d . . .
H6 H 0.0221 0.2685 0.2736 0.031 Uiso 1 calc . . R
C7 C 0.1125(5) 0.3955(2) 0.4137(6) 0.0173(9) Uani 1 d . . .
C8 C 0.4593(5) 0.1244(2) 0.5178(6) 0.0165(9) Uani 1 d . . .
C9 C 0.0574(5) 0.5243(2) 1.0715(6) 0.0163(9) Uani 1 d . . .
O9 O 0.2085(8) 0.7602(4) 0.5282(10) 0.0659(19) Uani 0.70 d . . D
H9A H 0.179(12) 0.796(4) 0.578(13) 0.099 Uiso 0.70 d . . DR
H9B H 0.129(9) 0.751(5) 0.436(9) 0.099 Uiso 0.70 d . . DR
H7A H 0.246(7) 0.6388(6) 0.498(8) 0.06(2) Uiso 1 d . . D
H7B H 0.179(4) 0.583(2) 0.405(3) 0.021(13) Uiso 1 d . . D
H8A H 0.600(4) 0.490(3) 0.756(6) 0.047(18) Uiso 1 d . . D
H8B H 0.538(10) 0.543(3) 0.643(11) 0.14(4) Uiso 1 d . . D


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Tb1 O1 2.278(3) . ?
Tb1 O2 2.342(3) 3_566 ?
Tb1 O3 2.339(3) 2_656 ?
Tb1 O4 2.291(3) 4_566 ?
Tb1 O5 2.432(3) . ?
Tb1 O6 2.463(3) 3_567 ?
Tb1 O7 2.476(3) . ?
Tb1 O8 2.469(3) . ?
O1 C7 1.253(5) . ?
O2 Tb1 2.342(3) 3_566 ?
O2 C7 1.260(5) . ?
O3 Tb1 2.339(3) 2_646 ?
O3 C8 1.258(5) . ?
O4 Tb1 2.291(3) 4_565 ?
O4 C8 1.249(5) . ?
O5 C9 1.251(5) . ?
O6 Tb1 2.463(3) 3_567 ?
O6 C9 1.254(5) . ?
O7 H7A 0.835(10) . ?
O7 H7B 0.836(10) . ?
O8 H8A 0.836(10) . ?
O8 H8B 0.837(10) . ?
C1 C2 1.391(6) . ?
C1 C6 1.385(6) . ?
C1 C7 1.499(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.374(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.381(6) . ?
C4 C5 1.393(6) . ?
C4 C8 1.502(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.368(6) . ?
C6 H6 0.9300 . ?
C9 C9 1.546(8) 3_567 ?
O9 H9A 0.85(2) . ?
O9 H9B 0.85(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Tb1 O2 103.73(11) . 3_566 ?
O1 Tb1 O3 144.33(11) . 2_656 ?
O1 Tb1 O4 90.22(11) . 4_566 ?
O1 Tb1 O5 141.32(10) . . ?
O1 Tb1 O6 76.15(10) . 3_567 ?
O1 Tb1 O7 74.50(12) . . ?
O1 Tb1 O8 78.39(12) . . ?
O2 Tb1 O5 74.77(11) 3_566 . ?
O2 Tb1 O6 72.11(10) 3_566 3_567 ?
O2 Tb1 O7 72.05(11) 3_566 . ?
O2 Tb1 O8 139.10(12) 3_566 . ?
O3 Tb1 O2 81.32(10) 2_656 3_566 ?
O3 Tb1 O5 74.32(10) 2_656 . ?
O3 Tb1 O6 137.01(10) 2_656 3_567 ?
O3 Tb1 O7 73.70(12) 2_656 . ?
O3 Tb1 O8 75.61(12) 2_656 . ?
O4 Tb1 O2 147.07(11) 4_566 3_566 ?
O4 Tb1 O3 104.57(11) 4_566 2_656 ?
O4 Tb1 O5 75.82(11) 4_566 . ?
O4 Tb1 O6 82.84(10) 4_566 3_567 ?
O4 Tb1 O7 140.87(12) 4_566 . ?
O4 Tb1 O8 72.46(12) 4_566 . ?
O5 Tb1 O6 66.53(9) . 3_567 ?
O5 Tb1 O7 136.59(11) . . ?
O5 Tb1 O8 128.38(11) . . ?
O6 Tb1 O7 125.80(11) 3_567 . ?
O6 Tb1 O8 144.20(11) 3_567 . ?
O8 Tb1 O7 69.28(12) . . ?
C7 O1 Tb1 166.4(3) . . ?
C7 O2 Tb1 130.3(3) . 3_566 ?
C8 O3 Tb1 126.4(3) . 2_646 ?
C8 O4 Tb1 175.7(3) . 4_565 ?
C9 O5 Tb1 118.1(3) . . ?
C9 O6 Tb1 117.2(3) . 3_567 ?
Tb1 O7 H7A 125(4) . . ?
Tb1 O7 H7B 115(3) . . ?
H7A O7 H7B 103(5) . . ?
Tb1 O8 H8A 125(4) . . ?
Tb1 O8 H8B 111(6) . . ?
H8A O8 H8B 105(7) . . ?
C2 C1 C7 120.9(4) . . ?
C6 C1 C2 119.2(4) . . ?
C6 C1 C7 119.8(4) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 C1 119.6(4) . . ?
C3 C2 H2 120.2 . . ?
C2 C3 H3 119.3 . . ?
C2 C3 C4 121.3(4) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 C5 118.7(4) . . ?
C3 C4 C8 121.4(4) . . ?
C5 C4 C8 119.9(4) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.2(4) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 H6 119.5 . . ?
C5 C6 C1 120.9(4) . . ?
C5 C6 H6 119.5 . . ?
O1 C7 O2 124.2(4) . . ?
O1 C7 C1 119.0(4) . . ?
O2 C7 C1 116.8(4) . . ?
O3 C8 C4 117.1(4) . . ?
O4 C8 O3 124.1(4) . . ?
O4 C8 C4 118.8(4) . . ?
O5 C9 O6 125.9(4) . . ?
O5 C9 C9 117.1(4) . 3_567 ?
O6 C9 C9 117.0(4) . 3_567 ?
H9A O9 H9B 107(5) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O7 H7A O9 0.835(10) 2.313(17) 3.138(9) 169(5) .
O7 H7B O6 0.836(10) 1.993(13) 2.822(5) 171(4) 1_554
O8 H8A O5 0.836(10) 1.984(14) 2.815(5) 172(6) 3_667

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
Tb1 O1 C7 O2 102.2(12) . . . . ?
Tb1 O1 C7 C1 -76.9(13) . . . . ?
Tb1 O2 C7 O1 -15.1(6) 3_566 . . . ?
Tb1 O2 C7 C1 164.1(3) 3_566 . . . ?
Tb1 O3 C8 O4 -12.7(6) 2_646 . . . ?
Tb1 O3 C8 C4 167.9(3) 2_646 . . . ?
Tb1 O4 C8 O3 -148(4) 4_565 . . . ?
Tb1 O4 C8 C4 31(4) 4_565 . . . ?
Tb1 O5 C9 O6 -164.4(3) . . . . ?
Tb1 O5 C9 C9 16.8(6) . . . 3_567 ?
Tb1 O6 C9 O5 -163.9(3) 3_567 . . . ?
Tb1 O6 C9 C9 14.8(6) 3_567 . . 3_567 ?
O1 Tb1 O5 C9 -33.6(4) . . . . ?
O2 Tb1 O1 C7 -93.8(12) 3_566 . . . ?
O2 Tb1 O5 C9 59.5(3) 3_566 . . . ?
O3 Tb1 O1 C7 172.0(12) 2_656 . . . ?
O3 Tb1 O5 C9 144.6(3) 2_656 . . . ?
O4 Tb1 O1 C7 56.1(12) 4_566 . . . ?
O4 Tb1 O5 C9 -105.5(3) 4_566 . . . ?
O5 Tb1 O1 C7 -11.1(13) . . . . ?
O6 Tb1 O1 C7 -26.5(12) 3_567 . . . ?
O6 Tb1 O5 C9 -17.3(3) 3_567 . . . ?
O7 Tb1 O1 C7 -160.4(12) . . . . ?
O7 Tb1 O5 C9 100.7(3) . . . . ?
O8 Tb1 O1 C7 128.1(12) . . . . ?
O8 Tb1 O5 C9 -158.9(3) . . . . ?
C1 C2 C3 C4 -0.6(7) . . . . ?
C2 C1 C6 C5 0.8(7) . . . . ?
C2 C1 C7 O1 -12.2(6) . . . . ?
C2 C1 C7 O2 168.6(4) . . . . ?
C2 C3 C4 C5 0.7(7) . . . . ?
C2 C3 C4 C8 179.2(4) . . . . ?
C3 C4 C5 C6 0.0(7) . . . . ?
C3 C4 C8 O3 3.3(6) . . . . ?
C3 C4 C8 O4 -176.1(4) . . . . ?
C4 C5 C6 C1 -0.7(7) . . . . ?
C5 C4 C8 O3 -178.2(4) . . . . ?
C5 C4 C8 O4 2.4(6) . . . . ?
C6 C1 C2 C3 -0.1(7) . . . . ?
C6 C1 C7 O1 162.9(4) . . . . ?
C6 C1 C7 O2 -16.3(6) . . . . ?
C7 C1 C2 C3 175.1(4) . . . . ?
C7 C1 C6 C5 -174.5(4) . . . . ?
C8 C4 C5 C6 -178.5(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_9
_database_code_depnum_ccdc_archive 'CCDC 1863672'
_audit_update_record             
;
2018-08-24 deposited with the CCDC.
2018-09-26 downloaded from the CCDC.
;
_audit_creation_date             2018-03-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H5 O6 Tb'
_chemical_formula_sum            'C10 H5 O6 Tb'
_chemical_formula_weight         380.06
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   14.0391(4)
_cell_length_b                   6.7782(2)
_cell_length_c                   21.9289(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2086.75(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8759
_cell_measurement_temperature    296
_cell_measurement_theta_max      27.107
_cell_measurement_theta_min      3.446
_shelx_estimated_absorpt_T_max   0.876
_shelx_estimated_absorpt_T_min   0.450
_exptl_absorpt_coefficient_mu    6.791
_exptl_absorpt_correction_T_max  0.3330
_exptl_absorpt_correction_T_min  0.2847
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0708 before and 0.0575 after correction. The Ratio of minimum to maximum transmission is 0.8550. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.419
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0580
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            29688
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.135
_diffrn_reflns_theta_min         3.446
_diffrn_ambient_temperature      296.0
_diffrn_detector                 'Bruker PHOTON 100 area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'PHOTON area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'four-circle KAPPA diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_collimation    '0.5 mm'
_diffrn_radiation_monochromator  'graphiteDouble Bounce Multilayer Mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed x-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Incoatec I\mus'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1920
_reflns_number_total             2304
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2016)'
_computing_data_collection       'APEX 3 (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'

_refine_diff_density_max         0.526
_refine_diff_density_min         -0.504
_refine_diff_density_rms         0.113
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2304
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0214
_refine_ls_restrained_S_all      1.093
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0042P)²+5.3790P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0345
_refine_ls_wR_factor_ref         0.0363
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C7(H7), C8(H8)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.66907(2) 1.04973(2) 0.55702(2) 0.01351(5) Uani 1 1 d . . . . .
O1 O 0.67047(17) 0.6946(3) 0.54867(11) 0.0220(5) Uani 1 1 d . . . . .
O2 O 0.67214(18) 0.3908(3) 0.51520(10) 0.0201(5) Uani 1 1 d . . . . .
O3 O 0.51370(17) 0.9929(4) 0.57209(10) 0.0255(6) Uani 1 1 d . . . . .
O4 O 0.36197(17) 0.9978(4) 0.54488(10) 0.0232(6) Uani 1 1 d . . . . .
O5 O 0.3732(2) 0.7780(4) 0.86805(12) 0.0347(7) Uani 1 1 d . . . . .
O6 O 0.2362(2) 0.9343(4) 0.85371(11) 0.0311(6) Uani 1 1 d . . . . .
C1 C 0.6278(2) 0.5479(6) 0.52514(16) 0.0187(7) Uani 1 1 d . . . . .
C2 C 0.5260(3) 0.5685(6) 0.5104(2) 0.0345(10) Uani 1 1 d . . . . .
H2 H 0.497911 0.691028 0.516688 0.041 Uiso 1 1 calc R . . . .
C3 C 0.3974(2) 0.9647(6) 0.64969(15) 0.0202(7) Uani 1 1 d . . . . .
C4 C 0.4647(3) 0.9076(7) 0.69308(17) 0.0308(10) Uani 1 1 d . . . . .
H4 H 0.527811 0.888835 0.681653 0.037 Uiso 1 1 calc R . . . .
C5 C 0.4376(3) 0.8789(7) 0.75299(17) 0.0323(10) Uani 1 1 d . . . . .
H5 H 0.482175 0.836782 0.781514 0.039 Uiso 1 1 calc R . . . .
C6 C 0.3448(3) 0.9123(5) 0.77071(15) 0.0230(8) Uani 1 1 d . . . . .
C7 C 0.2779(3) 0.9719(7) 0.72812(16) 0.0296(9) Uani 1 1 d . . . . .
H7 H 0.215343 0.995590 0.740023 0.036 Uiso 1 1 calc R . . . .
C8 C 0.3045(3) 0.9964(6) 0.66741(16) 0.0248(9) Uani 1 1 d . . . . .
H8 H 0.259340 1.034228 0.638685 0.030 Uiso 1 1 calc R . . . .
C9 C 0.4264(2) 0.9881(5) 0.58425(15) 0.0172(7) Uani 1 1 d . . . . .
C10 C 0.3157(3) 0.8722(6) 0.83543(16) 0.0246(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 O1 2.414(2) . ?
Tb1 O1 2.464(2) 8_765 ?
Tb1 O2 2.640(2) 8_765 ?
Tb1 O2 2.488(2) 1_565 ?
Tb1 O3 2.239(2) . ?
Tb1 O4 2.299(2) 5_676 ?
Tb1 O5 2.333(3) 3_656 ?
Tb1 O6 2.309(2) 6_657 ?
O1 C1 1.270(4) . ?
O2 C1 1.252(4) . ?
O3 C9 1.255(4) . ?
O4 C9 1.252(4) . ?
O5 C10 1.254(5) . ?
O6 C10 1.259(5) . ?
C1 C2 1.472(5) . ?
C2 C2 1.266(8) 5_666 ?
C2 H2 0.9300 . ?
C3 C4 1.395(5) . ?
C3 C8 1.378(5) . ?
C3 C9 1.500(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.382(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.378(5) . ?
C6 C7 1.384(5) . ?
C6 C10 1.502(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.393(5) . ?
C8 H8 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Tb1 O1 112.59(6) . 8_765 ?
O1 Tb1 O2 65.57(8) 8_765 1_565 ?
O1 Tb1 O2 63.90(8) . 8_765 ?
O1 Tb1 O2 153.98(8) . 1_565 ?
O1 Tb1 O2 50.57(7) 8_765 8_765 ?
O2 Tb1 O2 103.68(7) 1_565 8_765 ?
O3 Tb1 O1 165.90(9) . 8_765 ?
O3 Tb1 O1 81.24(9) . . ?
O3 Tb1 O2 143.46(9) . 8_765 ?
O3 Tb1 O2 103.36(9) . 1_565 ?
O3 Tb1 O4 86.26(8) . 5_676 ?
O3 Tb1 O5 76.26(10) . 3_656 ?
O3 Tb1 O6 102.36(9) . 6_657 ?
O4 Tb1 O1 77.78(9) 5_676 . ?
O4 Tb1 O1 99.02(8) 5_676 8_765 ?
O4 Tb1 O2 77.00(9) 5_676 1_565 ?
O4 Tb1 O2 76.43(8) 5_676 8_765 ?
O4 Tb1 O5 136.80(10) 5_676 3_656 ?
O4 Tb1 O6 148.63(10) 5_676 6_657 ?
O5 Tb1 O1 135.77(9) 3_656 . ?
O5 Tb1 O1 91.18(9) 3_656 8_765 ?
O5 Tb1 O2 136.86(9) 3_656 8_765 ?
O5 Tb1 O2 69.38(9) 3_656 1_565 ?
O6 Tb1 O1 73.93(9) 6_657 . ?
O6 Tb1 O1 79.92(9) 6_657 8_765 ?
O6 Tb1 O2 79.15(9) 6_657 8_765 ?
O6 Tb1 O2 128.34(9) 6_657 1_565 ?
O6 Tb1 O5 74.42(10) 6_657 3_656 ?
Tb1 O1 Tb1 113.52(9) . 8_755 ?
C1 O1 Tb1 98.6(2) . 8_755 ?
C1 O1 Tb1 143.8(2) . . ?
Tb1 O2 Tb1 105.41(8) 1_545 8_755 ?
C1 O2 Tb1 90.7(2) . 8_755 ?
C1 O2 Tb1 135.8(2) . 1_545 ?
C9 O3 Tb1 170.8(3) . . ?
C9 O4 Tb1 143.1(2) . 5_676 ?
C10 O5 Tb1 125.2(3) . 3_646 ?
C10 O6 Tb1 138.2(2) . 6_557 ?
O1 C1 Tb1 56.09(16) . 8_755 ?
O1 C1 C2 118.2(4) . . ?
O2 C1 Tb1 64.05(17) . 8_755 ?
O2 C1 O1 120.1(3) . . ?
O2 C1 C2 121.7(4) . . ?
C2 C1 Tb1 174.2(3) . 8_755 ?
C1 C2 H2 117.6 . . ?
C2 C2 C1 124.7(5) 5_666 . ?
C2 C2 H2 117.6 5_666 . ?
C4 C3 C9 119.9(3) . . ?
C8 C3 C4 119.4(3) . . ?
C8 C3 C9 120.7(3) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.1(4) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.3(4) . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C7 119.9(3) . . ?
C5 C6 C10 119.6(3) . . ?
C7 C6 C10 120.4(3) . . ?
C6 C7 H7 120.1 . . ?
C6 C7 C8 119.8(3) . . ?
C8 C7 H7 120.1 . . ?
C3 C8 C7 120.3(3) . . ?
C3 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
O3 C9 C3 118.1(3) . . ?
O4 C9 O3 123.9(3) . . ?
O4 C9 C3 118.0(3) . . ?
O5 C10 O6 124.0(3) . . ?
O5 C10 C6 117.2(3) . . ?
O6 C10 C6 118.8(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
C2 H2 O3 0.93 2.39 3.184(5) 143.2 .

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
Tb1 O1 C1 Tb1 153.0(4) . . . 8_755 ?
Tb1 O1 C1 O2 154.3(3) . . . . ?
Tb1 O1 C1 O2 1.3(4) 8_755 . . . ?
Tb1 O1 C1 C2 -25.9(6) . . . . ?
Tb1 O1 C1 C2 -178.9(3) 8_755 . . . ?
Tb1 O2 C1 Tb1 113.2(3) 1_545 . . 8_755 ?
Tb1 O2 C1 O1 -1.2(3) 8_755 . . . ?
Tb1 O2 C1 O1 112.0(3) 1_545 . . . ?
Tb1 O2 C1 C2 -67.8(5) 1_545 . . . ?
Tb1 O2 C1 C2 179.0(3) 8_755 . . . ?
Tb1 O4 C9 O3 21.5(6) 5_676 . . . ?
Tb1 O4 C9 C3 -157.1(3) 5_676 . . . ?
Tb1 O5 C10 O6 35.6(5) 3_646 . . . ?
Tb1 O5 C10 C6 -144.4(3) 3_646 . . . ?
Tb1 O6 C10 O5 32.6(6) 6_557 . . . ?
Tb1 O6 C10 C6 -147.3(3) 6_557 . . . ?
O1 C1 C2 C2 -176.3(6) . . . 5_666 ?
O2 C1 C2 C2 3.5(9) . . . 5_666 ?
C3 C4 C5 C6 -2.0(7) . . . . ?
C4 C3 C8 C7 0.1(6) . . . . ?
C4 C3 C9 O3 -13.5(6) . . . . ?
C4 C3 C9 O4 165.1(4) . . . . ?
C4 C5 C6 C7 1.0(6) . . . . ?
C4 C5 C6 C10 177.5(4) . . . . ?
C5 C6 C7 C8 0.5(6) . . . . ?
C5 C6 C10 O5 -12.0(6) . . . . ?
C5 C6 C10 O6 168.0(4) . . . . ?
C6 C7 C8 C3 -1.1(6) . . . . ?
C7 C6 C10 O5 164.4(4) . . . . ?
C7 C6 C10 O6 -15.6(6) . . . . ?
C8 C3 C4 C5 1.4(7) . . . . ?
C8 C3 C9 O3 167.4(4) . . . . ?
C8 C3 C9 O4 -14.0(6) . . . . ?
C9 C3 C4 C5 -177.6(4) . . . . ?
C9 C3 C8 C7 179.2(4) . . . . ?
C10 C6 C7 C8 -175.9(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_11sm
_database_code_depnum_ccdc_archive 'CCDC 1863674'
_audit_update_record             
;
2018-08-24 deposited with the CCDC.
2018-09-26 downloaded from the CCDC.
;
_audit_creation_date             2018-08-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C9 H8 O8 Sm, 0.7(H2 O1)'
_chemical_formula_sum            'C9 H9.40 O8.70 Sm'
_chemical_formula_weight         407.12
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sm Sm -0.1638 3.4418 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.3815(3)
_cell_length_b                   18.8425(6)
_cell_length_c                   7.8522(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.3107(11)
_cell_angle_gamma                90.00
_cell_volume                     1190.18(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8234
_cell_measurement_temperature    296
_cell_measurement_theta_max      28.34
_cell_measurement_theta_min      2.91
_exptl_absorpt_coefficient_mu    4.971
_exptl_absorpt_correction_T_max  0.2627
_exptl_absorpt_correction_T_min  0.2248
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0738 before and 0.0610 after correction. The Ratio of minimum to maximum transmission is 0.8557. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            'light brown'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    2.272
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             780
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0657
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            31182
_diffrn_reflns_theta_full        28.35
_diffrn_reflns_theta_max         28.35
_diffrn_reflns_theta_min         2.91
_diffrn_ambient_temperature      296
_diffrn_detector                 'Bruker PHOTON 100 area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'PHOTON area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'four-circle KAPPA diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_collimation    '0.5 mm'
_diffrn_radiation_monochromator  'graphiteDouble Bounce Multilayer Mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed x-ray tube'
_diffrn_source_type              'Incoatec I\mus'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                2457
_reflns_number_total             2973
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.135
_refine_diff_density_min         -0.479
_refine_diff_density_rms         0.127
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2973
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0253
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0172P)²+1.6005P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0461
_refine_ls_wR_factor_ref         0.0494
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 O9-H9A = O9-H9B
 0.85 with sigma of 0.02
 O7-H7A = O7-H7B = O8-H8A
 0.84 with sigma of 0.01
 O8-H8B
 0.84 with sigma of 0.01
 H9A-H9B
 1.34 with sigma of 0.04
3. Others
 Fixed Sof: O9(0.7) H9A(0.7) H9B(0.7)
4.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Sm1 Sm 0.24452(2) 0.519673(8) 0.76082(2) 0.01573(6) Uani 1 d . . .
O1 O 0.1667(3) 0.44392(14) 0.5187(3) 0.0298(6) Uani 1 d . . .
O2 O -0.0202(3) 0.39725(13) 0.2875(3) 0.0299(6) Uani 1 d . . .
O3 O 0.6045(3) 0.12439(14) 0.6256(3) 0.0300(6) Uani 1 d . . .
O4 O 0.3909(3) 0.07284(13) 0.4348(3) 0.0305(6) Uani 1 d . . .
O5 O 0.1982(3) 0.53788(13) 1.0542(3) 0.0244(6) Uani 1 d . . .
O6 O 0.0024(3) 0.54421(13) 1.1961(3) 0.0212(5) Uani 1 d . . .
O7 O 0.2466(4) 0.59411(18) 0.4954(4) 0.0350(6) Uani 1 d . . D
H7A H 0.255(7) 0.6377(8) 0.515(7) 0.072(19) Uiso 1 d . . D
H7B H 0.180(6) 0.580(3) 0.401(5) 0.10(2) Uiso 1 d . . D
O8 O 0.5149(3) 0.50578(19) 0.6849(4) 0.0364(7) Uani 1 d . . D
H8A H 0.593(4) 0.485(2) 0.758(5) 0.056(16) Uiso 1 d . . D
H8B H 0.552(9) 0.540(3) 0.641(9) 0.14(3) Uiso 1 d . . D
O9 O 0.2077(7) 0.7594(4) 0.5272(9) 0.088(2) Uani 0.70 d . . D
H9A H 0.150(11) 0.742(6) 0.594(10) 0.132 Uiso 0.70 d . . DR
H9B H 0.147(11) 0.747(6) 0.421(5) 0.132 Uiso 0.70 d . . DR
C1 C 0.2067(4) 0.32574(18) 0.4351(4) 0.0212(7) Uani 1 d . . .
C2 C 0.3673(4) 0.32153(19) 0.5431(5) 0.0278(8) Uani 1 d . . .
H2 H 0.4205 0.3622 0.5982 0.033 Uiso 1 calc . . R
C3 C 0.4500(4) 0.2571(2) 0.5702(5) 0.0285(8) Uani 1 d . . .
H3 H 0.5588 0.2549 0.6425 0.034 Uiso 1 calc . . R
C4 C 0.3722(4) 0.19588(18) 0.4905(4) 0.0209(7) Uani 1 d . . .
C5 C 0.2109(5) 0.2003(2) 0.3815(5) 0.0306(9) Uani 1 d . . .
H5 H 0.1572 0.1596 0.3271 0.037 Uiso 1 calc . . R
C6 C 0.1294(5) 0.2646(2) 0.3531(5) 0.0340(9) Uani 1 d . . .
H6 H 0.0216 0.2671 0.2784 0.041 Uiso 1 calc . . R
C7 C 0.1117(4) 0.39426(18) 0.4114(4) 0.0209(7) Uani 1 d . . .
C8 C 0.4609(4) 0.12600(18) 0.5185(4) 0.0203(7) Uani 1 d . . .
C9 C 0.0580(4) 0.52393(18) 1.0729(4) 0.0191(7) Uani 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 O1 2.320(2) . ?
Sm1 O2 2.394(2) 3_566 ?
Sm1 O3 2.378(2) 2_656 ?
Sm1 O4 2.339(2) 4_566 ?
Sm1 O5 2.465(2) . ?
Sm1 O6 2.498(2) 3_567 ?
Sm1 O7 2.516(3) . ?
Sm1 O8 2.513(3) . ?
O1 C7 1.257(4) . ?
O2 Sm1 2.394(2) 3_566 ?
O2 C7 1.252(4) . ?
O3 Sm1 2.378(2) 2_646 ?
O3 C8 1.260(4) . ?
O4 Sm1 2.339(2) 4_565 ?
O4 C8 1.250(4) . ?
O5 C9 1.252(4) . ?
O6 Sm1 2.498(2) 3_567 ?
O6 C9 1.246(4) . ?
O7 H7A 0.834(10) . ?
O7 H7B 0.838(10) . ?
O8 H8A 0.835(10) . ?
O8 H8B 0.838(10) . ?
O9 H9A 0.87(2) . ?
O9 H9B 0.87(2) . ?
C1 C2 1.377(5) . ?
C1 C6 1.388(5) . ?
C1 C7 1.501(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.385(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.385(5) . ?
C4 C5 1.385(5) . ?
C4 C8 1.498(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.378(5) . ?
C6 H6 0.9300 . ?
C9 C9 1.564(6) 3_567 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Sm1 O2 104.18(9) . 3_566 ?
O1 Sm1 O3 144.62(10) . 2_656 ?
O1 Sm1 O4 90.05(9) . 4_566 ?
O1 Sm1 O5 140.32(9) . . ?
O1 Sm1 O6 76.20(9) . 3_567 ?
O1 Sm1 O7 74.33(10) . . ?
O1 Sm1 O8 78.83(10) . . ?
O2 Sm1 O5 74.58(9) 3_566 . ?
O2 Sm1 O6 72.11(9) 3_566 3_567 ?
O2 Sm1 O7 72.06(10) 3_566 . ?
O2 Sm1 O8 138.68(10) 3_566 . ?
O3 Sm1 O2 80.12(9) 2_656 3_566 ?
O3 Sm1 O5 74.99(9) 2_656 . ?
O3 Sm1 O6 136.29(8) 2_656 3_567 ?
O3 Sm1 O7 73.82(10) 2_656 . ?
O3 Sm1 O8 75.82(10) 2_656 . ?
O4 Sm1 O2 147.13(9) 4_566 3_566 ?
O4 Sm1 O3 105.24(9) 4_566 2_656 ?
O4 Sm1 O5 75.66(9) 4_566 . ?
O4 Sm1 O6 83.13(8) 4_566 3_567 ?
O4 Sm1 O7 140.80(10) 4_566 . ?
O4 Sm1 O8 72.60(10) 4_566 . ?
O5 Sm1 O6 65.58(7) . 3_567 ?
O5 Sm1 O7 137.38(10) . . ?
O5 Sm1 O8 128.69(9) . . ?
O6 Sm1 O7 125.41(9) 3_567 . ?
O6 Sm1 O8 144.92(9) 3_567 . ?
O8 Sm1 O7 69.23(10) . . ?
C7 O1 Sm1 166.7(2) . . ?
C7 O2 Sm1 129.4(2) . 3_566 ?
C8 O3 Sm1 125.3(2) . 2_646 ?
C8 O4 Sm1 174.9(2) . 4_565 ?
C9 O5 Sm1 118.7(2) . . ?
C9 O6 Sm1 117.5(2) . 3_567 ?
Sm1 O7 H7A 115(4) . . ?
Sm1 O7 H7B 114(4) . . ?
H7A O7 H7B 118(6) . . ?
Sm1 O8 H8A 118(3) . . ?
Sm1 O8 H8B 119(6) . . ?
H8A O8 H8B 109(6) . . ?
H9A O9 H9B 102(4) . . ?
C2 C1 C6 119.1(3) . . ?
C2 C1 C7 121.2(3) . . ?
C6 C1 C7 119.6(3) . . ?
C1 C2 H2 119.8 . . ?
C1 C2 C3 120.4(3) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.6(3) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 C5 118.9(3) . . ?
C3 C4 C8 121.0(3) . . ?
C5 C4 C8 120.1(3) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.4(3) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 H6 119.7 . . ?
C5 C6 C1 120.6(3) . . ?
C5 C6 H6 119.7 . . ?
O1 C7 C1 118.4(3) . . ?
O2 C7 O1 124.4(3) . . ?
O2 C7 C1 117.2(3) . . ?
O3 C8 C4 117.4(3) . . ?
O4 C8 O3 123.4(3) . . ?
O4 C8 C4 119.1(3) . . ?
O5 C9 C9 116.5(3) . 3_567 ?
O6 C9 O5 126.5(3) . . ?
O6 C9 C9 117.0(3) . 3_567 ?

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 O9 0.834(10) 2.334(19) 3.148(9) 165(5) .
O7 H7B O6 0.838(10) 1.977(14) 2.810(4) 173(6) 1_554
O8 H8A O5 0.835(10) 1.994(17) 2.809(4) 165(5) 3_667

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
Sm1 O1 C7 O2 103.2(10) . . . . ?
Sm1 O1 C7 C1 -75.0(11) . . . . ?
Sm1 O2 C7 O1 -15.0(5) 3_566 . . . ?
Sm1 O2 C7 C1 163.3(2) 3_566 . . . ?
Sm1 O3 C8 O4 -12.8(5) 2_646 . . . ?
Sm1 O3 C8 C4 167.9(2) 2_646 . . . ?
Sm1 O4 C8 O3 -160(3) 4_565 . . . ?
Sm1 O4 C8 C4 19(3) 4_565 . . . ?
Sm1 O5 C9 O6 -162.9(3) . . . . ?
Sm1 O5 C9 C9 17.3(5) . . . 3_567 ?
Sm1 O6 C9 O5 -163.2(3) 3_567 . . . ?
Sm1 O6 C9 C9 16.6(5) 3_567 . . 3_567 ?
O1 Sm1 O5 C9 -34.9(3) . . . . ?
O2 Sm1 O1 C7 -94.7(10) 3_566 . . . ?
O2 Sm1 O5 C9 58.8(2) 3_566 . . . ?
O3 Sm1 O1 C7 172.4(10) 2_656 . . . ?
O3 Sm1 O5 C9 142.5(3) 2_656 . . . ?
O4 Sm1 O1 C7 55.3(10) 4_566 . . . ?
O4 Sm1 O5 C9 -107.1(3) 4_566 . . . ?
O5 Sm1 O1 C7 -11.9(11) . . . . ?
O6 Sm1 O1 C7 -27.6(10) 3_567 . . . ?
O6 Sm1 O5 C9 -18.2(2) 3_567 . . . ?
O7 Sm1 O1 C7 -161.1(10) . . . . ?
O7 Sm1 O5 C9 98.3(3) . . . . ?
O8 Sm1 O1 C7 127.6(10) . . . . ?
O8 Sm1 O5 C9 -160.2(2) . . . . ?
C1 C2 C3 C4 -0.6(6) . . . . ?
C2 C1 C6 C5 1.0(6) . . . . ?
C2 C1 C7 O1 -14.6(5) . . . . ?
C2 C1 C7 O2 167.1(3) . . . . ?
C2 C3 C4 C5 0.8(6) . . . . ?
C2 C3 C4 C8 179.8(3) . . . . ?
C3 C4 C5 C6 0.0(6) . . . . ?
C3 C4 C8 O3 4.3(5) . . . . ?
C3 C4 C8 O4 -175.1(3) . . . . ?
C4 C5 C6 C1 -0.9(6) . . . . ?
C5 C4 C8 O3 -176.7(3) . . . . ?
C5 C4 C8 O4 3.9(5) . . . . ?
C6 C1 C2 C3 -0.3(6) . . . . ?
C6 C1 C7 O1 162.4(4) . . . . ?
C6 C1 C7 O2 -15.9(5) . . . . ?
C7 C1 C2 C3 176.8(3) . . . . ?
C7 C1 C6 C5 -176.1(4) . . . . ?
C8 C4 C5 C6 -179.1(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_3sm
_database_code_depnum_ccdc_archive 'CCDC 1863666'
_audit_update_record             
;
2018-08-24 deposited with the CCDC.
2018-09-26 downloaded from the CCDC.
;
_audit_creation_date             2018-03-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H16 O16 Sm2, 2(H2 O)'
_chemical_formula_sum            'C16 H20 O18 Sm2'
_chemical_formula_weight         801.02
_chemical_absolute_configuration unk
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sm Sm -0.1638 3.4418 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.0276(2)
_cell_length_b                   12.5114(3)
_cell_length_c                   10.4264(2)
_cell_angle_alpha                90
_cell_angle_beta                 103.2380(10)
_cell_angle_gamma                90
_cell_volume                     1146.35(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2201
_cell_measurement_temperature    296
_cell_measurement_theta_max      30.574
_cell_measurement_theta_min      3.150
_shelx_estimated_absorpt_T_max   0.820
_shelx_estimated_absorpt_T_min   0.532
_exptl_absorpt_coefficient_mu    5.161
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6837
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0728 before and 0.0667 after correction. The Ratio of minimum to maximum transmission is 0.9164. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.321
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0620
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            75933
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.574
_diffrn_reflns_theta_min         3.150
_diffrn_ambient_temperature      296
_diffrn_detector                 'Bruker PHOTON 100 area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'PHOTON area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'four-circle KAPPA diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST CMOS'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    '0.5 mm'
_diffrn_radiation_monochromator  'graphiteDouble Bounce Multilayer Mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed x-ray tube'
_diffrn_source_type              'Incoatec I\mus'
_reflns_Friedel_coverage         0.919
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                6572
_reflns_number_total             7002
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2016)'
_computing_data_collection       'APEX 3 (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'

_refine_diff_density_max         0.808
_refine_diff_density_min         -0.506
_refine_diff_density_rms         0.111
_refine_ls_abs_structure_details 
;
 Flack x determined using 2994 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.002(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     373
_refine_ls_number_reflns         7002
_refine_ls_number_restraints     19
_refine_ls_R_factor_all          0.0247
_refine_ls_R_factor_gt           0.0202
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0161P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0360
_refine_ls_wR_factor_ref         0.0368
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 O14-H14A = O16-H16A
 0.84 with sigma of 0.01
 O14-H14B
 0.84 with sigma of 0.01
 H14A-H14B
 1.37 with sigma of 0.02
 O13-H13A
 0.84 with sigma of 0.01
 O17-H17A
 0.84 with sigma of 0.01
 O16-H16B
 0.84 with sigma of 0.01
 H16A-H16B
 1.355 with sigma of 0.02
 O17-H17B
 0.84 with sigma of 0.01
 H17A-H17B
 1.35 with sigma of 0.02
 O13-H13B
 0.84 with sigma of 0.01
 H13B-H13A
 1.365 with sigma of 0.02
 O15-H15A
 0.84 with sigma of 0.01
 O15-H15B
 0.84 with sigma of 0.01
 H15B-H15A
 1.37 with sigma of 0.02
 O18-H18A
 0.84 with sigma of 0.01
 O18-H18B
 0.84 with sigma of 0.01
 H18A-H18B
 1.39 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C10(H10), C11(H11), C14(H14), C15(H15)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.38442(2) 0.58956(2) 0.67949(2) 0.01286(5) Uani 1 1 d . . . . .
Sm2 Sm 0.07391(2) 0.50560(2) 0.88305(2) 0.01226(5) Uani 1 1 d . . . . .
O1 O 0.4402(4) 0.6196(3) 0.4617(4) 0.0360(10) Uani 1 1 d . . . . .
O2 O 0.5999(3) 0.5142(4) 0.5885(3) 0.0305(8) Uani 1 1 d . . . . .
O3 O 0.8580(4) 0.5706(3) -0.0287(3) 0.0308(9) Uani 1 1 d . . . . .
O4 O 1.0376(5) 0.4889(4) 0.1121(4) 0.0482(13) Uani 1 1 d . . . . .
O5 O 0.1344(4) 0.6558(3) 0.5788(3) 0.0258(8) Uani 1 1 d . . . . .
O6 O -0.0240(4) 0.6278(3) 0.7128(3) 0.0253(8) Uani 1 1 d . . . . .
O7 O -0.1855(4) 0.9444(3) 0.2892(3) 0.0208(7) Uani 1 1 d . . . . .
O8 O -0.2797(5) 0.9345(3) 0.4617(4) 0.0357(10) Uani 1 1 d . . . . .
O9 O 0.4880(4) 0.4741(3) 0.8588(3) 0.0237(7) Uani 1 1 d . . . . .
O10 O 0.3261(4) 0.4508(3) 0.9905(3) 0.0252(8) Uani 1 1 d . . . . .
O11 O 0.8559(5) 0.1767(3) 1.0031(4) 0.0447(11) Uani 1 1 d . . . . .
O12 O 0.7097(4) 0.1585(3) 1.1416(3) 0.0222(7) Uani 1 1 d . . . . .
O13 O 0.3920(5) 0.7856(3) 0.6403(5) 0.0459(11) Uani 1 1 d D . . . .
H13A H 0.467(5) 0.825(5) 0.644(7) 0.06(2) Uiso 1 1 d D . . . .
H13B H 0.379(12) 0.747(9) 0.573(8) 0.20(7) Uiso 1 1 d D . . . .
O14 O 0.6272(4) 0.6694(3) 0.8012(4) 0.0303(8) Uani 1 1 d D . . . .
H14A H 0.696(6) 0.630(5) 0.845(7) 0.09(3) Uiso 1 1 d D . . . .
H14B H 0.669(8) 0.721(5) 0.773(9) 0.13(4) Uiso 1 1 d D . . . .
O15 O 0.0752(5) 0.3104(3) 0.9317(5) 0.0433(10) Uani 1 1 d D . . . .
H15A H 0.017(12) 0.306(10) 0.984(11) 0.22(7) Uiso 1 1 d D . . . .
H15B H 0.138(8) 0.260(5) 0.946(9) 0.10(3) Uiso 1 1 d D . . . .
O16 O -0.1496(4) 0.4208(3) 0.7480(4) 0.0282(8) Uani 1 1 d D . . . .
H16A H -0.220(4) 0.456(3) 0.702(5) 0.032(16) Uiso 1 1 d D . . . .
H16B H -0.169(6) 0.3559(13) 0.736(5) 0.035(16) Uiso 1 1 d D . . . .
O17 O 0.6663(5) 0.8868(4) 0.7183(5) 0.0470(11) Uani 1 1 d D . . . .
H17A H 0.690(11) 0.934(5) 0.669(6) 0.12(4) Uiso 1 1 d D . . . .
H17B H 0.707(9) 0.905(6) 0.796(3) 0.08(3) Uiso 1 1 d D . . . .
O18 O -0.1950(7) 0.2094(4) 0.7181(5) 0.0622(14) Uani 1 1 d D . . . .
H18A H -0.195(11) 0.187(8) 0.794(3) 0.14(5) Uiso 1 1 d D . . . .
H18B H -0.259(6) 0.179(5) 0.659(5) 0.06(2) Uiso 1 1 d D . . . .
C1 C 0.6525(5) 0.5601(4) 0.3813(5) 0.0205(10) Uani 1 1 d . . . . .
C2 C 0.5977(6) 0.6050(5) 0.2574(5) 0.0314(13) Uani 1 1 d . . . . .
H2 H 0.504267 0.639933 0.238700 0.038 Uiso 1 1 calc R . . . .
C3 C 0.6814(5) 0.5980(6) 0.1617(5) 0.0305(12) Uani 1 1 d . . . . .
H3 H 0.643638 0.627167 0.078597 0.037 Uiso 1 1 calc R . . . .
C4 C 0.8223(6) 0.5472(4) 0.1904(5) 0.0232(10) Uani 1 1 d . . . . .
C5 C 0.8788(5) 0.5062(6) 0.3134(5) 0.0278(10) Uani 1 1 d . . . . .
H5 H 0.974518 0.474468 0.333189 0.033 Uiso 1 1 calc R . . . .
C6 C 0.7944(5) 0.5115(5) 0.4089(4) 0.0240(9) Uani 1 1 d . . . . .
H6 H 0.833097 0.482348 0.491820 0.029 Uiso 1 1 calc R . . . .
C7 C 0.5599(5) 0.5644(4) 0.4838(5) 0.0198(10) Uani 1 1 d . . . . .
C8 C 0.9106(6) 0.5345(4) 0.0864(5) 0.0207(11) Uani 1 1 d . . . . .
C9 C 0.0147(5) 0.6738(4) 0.6194(4) 0.0200(9) Uani 1 1 d . . . . .
C10 C -0.0899(6) 0.7603(4) 0.5555(5) 0.0282(11) Uani 1 1 d . . . . .
H10 H -0.166216 0.780459 0.597208 0.034 Uiso 1 1 calc R . . . .
C11 C -0.0854(5) 0.8105(4) 0.4473(5) 0.0241(10) Uani 1 1 d . . . . .
H11 H -0.014451 0.789668 0.400034 0.029 Uiso 1 1 calc R . . . .
C12 C -0.1899(5) 0.9000(4) 0.3971(5) 0.0200(9) Uani 1 1 d . . . . .
C13 C 0.4453(5) 0.4294(4) 0.9519(5) 0.0193(9) Uani 1 1 d . . . . .
C14 C 0.5394(5) 0.3399(4) 1.0213(5) 0.0240(10) Uani 1 1 d . . . . .
H14 H 0.509667 0.308182 1.092049 0.029 Uiso 1 1 calc R . . . .
C15 C 0.6603(6) 0.3035(4) 0.9889(5) 0.0253(10) Uani 1 1 d . . . . .
H15 H 0.695426 0.339399 0.923562 0.030 Uiso 1 1 calc R . . . .
C16 C 0.7460(5) 0.2080(4) 1.0497(5) 0.0211(10) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Sm1 O1 2.465(3) . ?
Sm1 O2 2.534(3) . ?
Sm1 O5 2.408(3) . ?
Sm1 O7 2.627(3) 2_546 ?
Sm1 O8 2.487(4) 2_546 ?
Sm1 O9 2.378(3) . ?
Sm1 O12 2.381(3) 2_657 ?
Sm1 O13 2.490(4) . ?
Sm1 H13B 2.26(13) . ?
Sm1 O14 2.477(4) . ?
Sm2 O3 2.476(3) 1_456 ?
Sm2 O4 2.492(3) 1_456 ?
Sm2 O6 2.356(3) . ?
Sm2 O7 2.378(3) 2_546 ?
Sm2 O10 2.396(3) . ?
Sm2 O11 2.459(4) 2_657 ?
Sm2 O12 2.788(3) 2_657 ?
Sm2 O15 2.494(4) . ?
Sm2 O16 2.424(3) . ?
O1 C7 1.258(6) . ?
O2 C7 1.238(6) . ?
O3 C8 1.268(6) . ?
O4 C8 1.254(6) . ?
O5 C9 1.268(6) . ?
O6 C9 1.249(5) . ?
O7 C12 1.264(5) . ?
O8 C12 1.244(6) . ?
O9 C13 1.255(5) . ?
O10 C13 1.262(5) . ?
O11 C16 1.263(6) . ?
O12 C16 1.246(5) . ?
O13 H13A 0.832(14) . ?
O13 H13B 0.837(14) . ?
O14 H14A 0.842(14) . ?
O14 H14B 0.838(15) . ?
O15 H15A 0.840(15) . ?
O15 H15B 0.837(14) . ?
O16 H16A 0.831(14) . ?
O16 H16B 0.834(14) . ?
O17 H17A 0.840(14) . ?
O17 H17B 0.837(14) . ?
O18 H18A 0.838(14) . ?
O18 H18B 0.835(14) . ?
C1 C2 1.391(7) . ?
C1 C6 1.387(6) . ?
C1 C7 1.502(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.386(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.392(7) . ?
C4 C5 1.367(7) . ?
C4 C8 1.494(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.387(6) . ?
C6 H6 0.9300 . ?
C9 C10 1.490(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.300(7) . ?
C11 H11 0.9300 . ?
C11 C12 1.480(6) . ?
C13 C14 1.489(6) . ?
C14 H14 0.9300 . ?
C14 C15 1.296(7) . ?
C15 H15 0.9300 . ?
C15 C16 1.485(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
O1 Sm1 O2 51.33(12) . . ?
O1 Sm1 O7 120.64(13) . 2_546 ?
O1 Sm1 O8 72.75(13) . 2_546 ?
O1 Sm1 O13 71.32(16) . . ?
O1 Sm1 H13B 53.2(11) . . ?
O1 Sm1 O14 93.85(14) . . ?
O2 Sm1 O7 113.26(13) . 2_546 ?
O2 Sm1 H13B 94(2) . . ?
O5 Sm1 O1 85.11(12) . . ?
O5 Sm1 O2 133.48(11) . . ?
O5 Sm1 O7 72.12(11) . 2_546 ?
O5 Sm1 O8 79.58(14) . 2_546 ?
O5 Sm1 O13 69.36(14) . . ?
O5 Sm1 H13B 65(3) . . ?
O5 Sm1 O14 135.67(14) . . ?
O7 Sm1 H13B 137(3) 2_546 . ?
O8 Sm1 O2 73.05(13) 2_546 . ?
O8 Sm1 O7 49.94(11) 2_546 2_546 ?
O8 Sm1 O13 133.79(16) 2_546 . ?
O8 Sm1 H13B 115.3(10) 2_546 . ?
O9 Sm1 O1 133.64(12) . . ?
O9 Sm1 O2 82.59(11) . . ?
O9 Sm1 O5 135.44(11) . . ?
O9 Sm1 O7 68.85(11) . 2_546 ?
O9 Sm1 O8 91.10(13) . 2_546 ?
O9 Sm1 O12 75.57(12) . 2_657 ?
O9 Sm1 O13 134.98(15) . . ?
O9 Sm1 H13B 151(2) . . ?
O9 Sm1 O14 72.53(13) . . ?
O12 Sm1 O1 148.36(12) 2_657 . ?
O12 Sm1 O2 150.50(11) 2_657 . ?
O12 Sm1 O5 75.53(12) 2_657 . ?
O12 Sm1 O7 77.07(10) 2_657 2_546 ?
O12 Sm1 O8 126.21(11) 2_657 2_546 ?
O12 Sm1 O13 78.46(16) 2_657 . ?
O12 Sm1 H13B 95.6(13) 2_657 . ?
O12 Sm1 O14 83.39(12) 2_657 . ?
O13 Sm1 O2 104.64(16) . . ?
O13 Sm1 O7 138.31(13) . 2_546 ?
O13 Sm1 H13B 19.5(5) . . ?
O14 Sm1 O2 71.15(13) . . ?
O14 Sm1 O7 139.90(12) . 2_546 ?
O14 Sm1 O8 142.14(14) . 2_546 ?
O14 Sm1 O13 68.44(15) . . ?
O14 Sm1 H13B 80(2) . . ?
O3 Sm2 O4 51.99(12) 1_456 1_456 ?
O3 Sm2 O12 115.90(12) 1_456 2_657 ?
O3 Sm2 O15 102.35(15) 1_456 . ?
O4 Sm2 O12 113.24(15) 1_456 2_657 ?
O4 Sm2 O15 73.65(18) 1_456 . ?
O6 Sm2 O3 82.83(12) . 1_456 ?
O6 Sm2 O4 131.87(13) . 1_456 ?
O6 Sm2 O7 77.92(12) . 2_546 ?
O6 Sm2 O10 133.68(12) . . ?
O6 Sm2 O11 79.03(14) . 2_657 ?
O6 Sm2 O12 68.61(11) . 2_657 ?
O6 Sm2 O15 140.55(15) . . ?
O6 Sm2 O16 74.20(12) . . ?
O7 Sm2 O3 153.15(11) 2_546 1_456 ?
O7 Sm2 O4 150.21(12) 2_546 1_456 ?
O7 Sm2 O10 74.91(12) 2_546 . ?
O7 Sm2 O11 122.55(12) 2_546 2_657 ?
O7 Sm2 O12 74.00(10) 2_546 2_657 ?
O7 Sm2 O15 81.66(15) 2_546 . ?
O7 Sm2 O16 81.98(12) 2_546 . ?
O10 Sm2 O3 131.67(11) . 1_456 ?
O10 Sm2 O4 81.19(12) . 1_456 ?
O10 Sm2 O11 84.90(15) . 2_657 ?
O10 Sm2 O12 68.20(11) . 2_657 ?
O10 Sm2 O15 70.41(13) . . ?
O10 Sm2 O16 136.18(13) . . ?
O11 Sm2 O3 70.87(12) 2_657 1_456 ?
O11 Sm2 O4 71.73(16) 2_657 1_456 ?
O11 Sm2 O12 48.61(11) 2_657 2_657 ?
O11 Sm2 O15 139.95(18) 2_657 . ?
O15 Sm2 O12 136.04(13) . 2_657 ?
O16 Sm2 O3 74.84(13) . 1_456 ?
O16 Sm2 O4 104.20(15) . 1_456 ?
O16 Sm2 O11 138.54(14) . 2_657 ?
O16 Sm2 O12 138.97(12) . 2_657 ?
O16 Sm2 O15 69.76(14) . . ?
C7 O1 Sm1 95.5(3) . . ?
C7 O2 Sm1 92.7(3) . . ?
C8 O3 Sm2 94.5(3) . 1_654 ?
C8 O4 Sm2 94.1(3) . 1_654 ?
C9 O5 Sm1 134.5(3) . . ?
C9 O6 Sm2 139.8(3) . . ?
Sm2 O7 Sm1 106.92(11) 2_556 2_556 ?
C12 O7 Sm1 91.8(3) . 2_556 ?
C12 O7 Sm2 156.8(3) . 2_556 ?
C12 O8 Sm1 99.0(3) . 2_556 ?
C13 O9 Sm1 138.1(3) . . ?
C13 O10 Sm2 134.4(3) . . ?
C16 O11 Sm2 102.9(3) . 2_647 ?
Sm1 O12 Sm2 101.95(11) 2_647 2_647 ?
C16 O12 Sm1 170.4(3) . 2_647 ?
C16 O12 Sm2 87.5(3) . 2_647 ?
Sm1 O13 H13A 129(5) . . ?
Sm1 O13 H13B 64(9) . . ?
H13A O13 H13B 109(4) . . ?
Sm1 O14 H14A 119(5) . . ?
Sm1 O14 H14B 123(6) . . ?
H14A O14 H14B 108(4) . . ?
Sm2 O15 H15A 103(8) . . ?
Sm2 O15 H15B 138(6) . . ?
H15A O15 H15B 109(4) . . ?
Sm2 O16 H16A 122(3) . . ?
Sm2 O16 H16B 129(3) . . ?
H16A O16 H16B 109(3) . . ?
H17A O17 H17B 107(4) . . ?
H18A O18 H18B 113(4) . . ?
C2 C1 C7 120.6(4) . . ?
C6 C1 C2 119.0(4) . . ?
C6 C1 C7 120.4(4) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.4(5) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.8(5) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 C8 120.4(4) . . ?
C5 C4 C3 119.9(4) . . ?
C5 C4 C8 119.6(4) . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.5(5) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 H6 119.8 . . ?
C5 C6 C1 120.3(4) . . ?
C5 C6 H6 119.8 . . ?
O1 C7 C1 118.9(4) . . ?
O2 C7 O1 120.3(4) . . ?
O2 C7 C1 120.7(4) . . ?
O3 C8 Sm2 59.4(2) . 1_654 ?
O3 C8 C4 120.1(4) . . ?
O4 C8 Sm2 60.1(2) . 1_654 ?
O4 C8 O3 119.4(4) . . ?
O4 C8 C4 120.5(4) . . ?
C4 C8 Sm2 178.3(3) . 1_654 ?
O5 C9 C10 118.8(4) . . ?
O6 C9 O5 126.2(4) . . ?
O6 C9 C10 115.0(4) . . ?
C9 C10 H10 116.7 . . ?
C11 C10 C9 126.6(5) . . ?
C11 C10 H10 116.7 . . ?
C10 C11 H11 119.1 . . ?
C10 C11 C12 121.8(5) . . ?
C12 C11 H11 119.1 . . ?
O7 C12 Sm1 62.9(2) . 2_556 ?
O7 C12 C11 119.9(4) . . ?
O8 C12 Sm1 56.4(2) . 2_556 ?
O8 C12 O7 119.2(4) . . ?
O8 C12 C11 120.9(4) . . ?
C11 C12 Sm1 174.5(4) . 2_556 ?
O9 C13 O10 126.0(4) . . ?
O9 C13 C14 118.0(4) . . ?
O10 C13 C14 116.0(4) . . ?
C13 C14 H14 118.0 . . ?
C15 C14 C13 123.9(4) . . ?
C15 C14 H14 118.0 . . ?
C14 C15 H15 118.0 . . ?
C14 C15 C16 124.0(4) . . ?
C16 C15 H15 118.0 . . ?
O11 C16 Sm2 52.9(2) . 2_647 ?
O11 C16 C15 117.6(4) . . ?
O12 C16 Sm2 68.0(3) . 2_647 ?
O12 C16 O11 120.7(4) . . ?
O12 C16 C15 121.7(4) . . ?
C15 C16 Sm2 168.3(3) . 2_647 ?

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
O13 H13A O17 0.832(14) 1.95(3) 2.734(6) 157(7) .
O14 H14A O3 0.842(14) 1.88(3) 2.706(5) 166(8) 1_556
O14 H14B O17 0.838(15) 2.15(5) 2.900(6) 150(8) .
O15 H15A O11 0.840(15) 2.21(11) 2.819(6) 129(12) 1_455
O15 H15B O3 0.837(14) 2.52(6) 3.178(6) 137(8) 2_646
O16 H16A O2 0.831(14) 1.921(18) 2.743(5) 170(5) 1_455
O16 H16B O18 0.834(14) 1.852(15) 2.683(6) 175(5) .
O17 H17A O8 0.840(14) 2.24(6) 2.889(6) 134(7) 1_655
O17 H17B O4 0.837(14) 2.52(6) 3.120(6) 130(7) 2_756
O17 H17B O10 0.837(14) 2.39(5) 3.124(6) 147(8) 2_657
O18 H18A O11 0.838(14) 2.13(3) 2.930(7) 160(8) 1_455
O18 H18B O1 0.835(14) 1.97(2) 2.789(6) 168(7) 2_546

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
Sm1 O1 C7 O2 4.3(5) . . . . ?
Sm1 O1 C7 C1 -175.9(3) . . . . ?
Sm1 O2 C7 O1 -4.2(5) . . . . ?
Sm1 O2 C7 C1 176.1(4) . . . . ?
Sm1 O5 C9 O6 -27.3(8) . . . . ?
Sm1 O5 C9 C10 150.2(4) . . . . ?
Sm1 O7 C12 O8 3.4(5) 2_556 . . . ?
Sm1 O7 C12 C11 -174.6(4) 2_556 . . . ?
Sm1 O8 C12 O7 -3.6(5) 2_556 . . . ?
Sm1 O8 C12 C11 174.4(4) 2_556 . . . ?
Sm1 O9 C13 O10 -13.5(8) . . . . ?
Sm1 O9 C13 C14 164.1(3) . . . . ?
Sm2 O3 C8 O4 2.3(5) 1_654 . . . ?
Sm2 O3 C8 C4 -178.2(4) 1_654 . . . ?
Sm2 O4 C8 O3 -2.3(5) 1_654 . . . ?
Sm2 O4 C8 C4 178.2(4) 1_654 . . . ?
Sm2 O6 C9 O5 7.9(9) . . . . ?
Sm2 O6 C9 C10 -169.8(4) . . . . ?
Sm2 O7 C12 Sm1 144.3(8) 2_556 . . 2_556 ?
Sm2 O7 C12 O8 147.7(6) 2_556 . . . ?
Sm2 O7 C12 C11 -30.3(11) 2_556 . . . ?
Sm2 O10 C13 O9 34.8(8) . . . . ?
Sm2 O10 C13 C14 -142.8(4) . . . . ?
Sm2 O11 C16 O12 6.6(6) 2_647 . . . ?
Sm2 O11 C16 C15 -171.9(4) 2_647 . . . ?
Sm2 O12 C16 O11 -5.7(5) 2_647 . . . ?
Sm2 O12 C16 C15 172.7(4) 2_647 . . . ?
O5 C9 C10 C11 11.4(8) . . . . ?
O6 C9 C10 C11 -170.8(5) . . . . ?
O9 C13 C14 C15 -2.0(8) . . . . ?
O10 C13 C14 C15 175.8(5) . . . . ?
C1 C2 C3 C4 -1.0(9) . . . . ?
C2 C1 C6 C5 -1.2(8) . . . . ?
C2 C1 C7 O1 -8.0(7) . . . . ?
C2 C1 C7 O2 171.7(5) . . . . ?
C2 C3 C4 C5 -1.2(9) . . . . ?
C2 C3 C4 C8 177.1(5) . . . . ?
C3 C4 C5 C6 2.2(9) . . . . ?
C3 C4 C8 O3 0.4(7) . . . . ?
C3 C4 C8 O4 179.9(6) . . . . ?
C4 C5 C6 C1 -1.0(9) . . . . ?
C5 C4 C8 O3 178.8(5) . . . . ?
C5 C4 C8 O4 -1.7(8) . . . . ?
C6 C1 C2 C3 2.2(8) . . . . ?
C6 C1 C7 O1 171.7(5) . . . . ?
C6 C1 C7 O2 -8.5(7) . . . . ?
C7 C1 C2 C3 -178.0(5) . . . . ?
C7 C1 C6 C5 179.0(5) . . . . ?
C8 C4 C5 C6 -176.1(5) . . . . ?
C9 C10 C11 C12 -176.2(5) . . . . ?
C10 C11 C12 O7 -177.5(5) . . . . ?
C10 C11 C12 O8 4.5(8) . . . . ?
C13 C14 C15 C16 -174.1(5) . . . . ?
C14 C15 C16 Sm2 141.4(14) . . . 2_647 ?
C14 C15 C16 O11 175.3(6) . . . . ?
C14 C15 C16 O12 -3.1(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_2tb
_database_code_depnum_ccdc_archive 'CCDC 1863665'
_audit_update_record             
;
2018-08-24 deposited with the CCDC.
2018-09-26 downloaded from the CCDC.
;
_audit_creation_date             2018-03-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H7 O8 Tb, C4 H3 O2, H2 O'
_chemical_formula_sum            'C10 H12 O11 Tb'
_chemical_formula_weight         467.12
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.1538(4)
_cell_length_b                   9.3150(4)
_cell_length_c                   9.7631(5)
_cell_angle_alpha                84.2320(17)
_cell_angle_beta                 65.5330(15)
_cell_angle_gamma                62.7110(16)
_cell_volume                     669.27(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3571
_cell_measurement_temperature    296
_cell_measurement_theta_max      26.402
_cell_measurement_theta_min      2.955
_shelx_estimated_absorpt_T_max   0.815
_shelx_estimated_absorpt_T_min   0.446
_exptl_absorpt_coefficient_mu    5.343
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6355
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0632 before and 0.0527 after correction. The Ratio of minimum to maximum transmission is 0.8526. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.318
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             450
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0535
_diffrn_reflns_av_unetI/netI     0.0602
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7872
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.427
_diffrn_reflns_theta_min         2.955
_diffrn_ambient_temperature      296.0
_diffrn_detector                 'Bruker PHOTON 100 area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'PHOTON area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'four-circle KAPPA diffractometer'
_diffrn_measurement_device_type  'BRUKER D8 QUEST CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_collimation    '0.5 mm'
_diffrn_radiation_monochromator  'graphiteDouble Bounce Multilayer Mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed x-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Incoatec I\mus'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2323
_reflns_number_total             2740
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2016)'
_computing_data_collection       'APEX 3 (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'

_refine_diff_density_max         0.967
_refine_diff_density_min         -1.420
_refine_diff_density_rms         0.200
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         2740
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0350
_refine_ls_restrained_S_all      1.096
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0006P)²+1.5151P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0510
_refine_ls_wR_factor_ref         0.0542
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 O11-H11B = O11-H11A
 0.84 with sigma of 0.01
 O7-H7B = O7-H7A
 0.84 with sigma of 0.01
 O10-H10
 0.82 with sigma of 0.01
 H7B-H7A
 1.42 with sigma of 0.02
 H11A-H11B
 1.37 with sigma of 0.02
 O8-H8A = O8-H8B
 0.84 with sigma of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C9(H9), C10(H10A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.23298(4) 0.51053(3) 0.53819(3) 0.01491(8) Uani 1 1 d . . . . .
O1 O 0.4610(5) 0.4217(4) 0.2670(4) 0.0207(9) Uani 1 1 d . . . . .
O2 O 0.2024(5) 0.6366(4) 0.3056(4) 0.0187(8) Uani 1 1 d . . . . .
O3 O 0.4018(6) 0.6536(5) 0.4789(5) 0.0287(10) Uani 1 1 d . . . . .
O4 O 0.5904(5) 0.7565(5) 0.4124(5) 0.0276(10) Uani 1 1 d . . . . .
O5 O 0.0257(5) 1.2215(4) 0.3869(4) 0.0202(9) Uani 1 1 d . . . . .
O6 O 0.1520(5) 1.3511(4) 0.4364(4) 0.0230(9) Uani 1 1 d . . . . .
O7 O 0.0206(5) 0.4550(5) 0.7542(5) 0.0244(9) Uani 1 1 d D . . . .
H7A H -0.032(8) 0.421(7) 0.723(6) 0.05(2) Uiso 1 1 d D . . . .
H7B H 0.063(9) 0.398(7) 0.813(7) 0.08(3) Uiso 1 1 d D . . . .
O8 O 0.2180(6) 0.5921(6) 0.7707(5) 0.0304(10) Uani 1 1 d D . . . .
H8A H 0.304(6) 0.605(8) 0.768(7) 0.04(2) Uiso 1 1 d D . . . .
H8B H 0.131(6) 0.642(7) 0.853(4) 0.05(2) Uiso 1 1 d D . . . .
C1 C 0.3611(7) 0.5336(6) 0.2168(6) 0.0144(11) Uani 1 1 d . . . . .
C2 C 0.4211(7) 0.5492(7) 0.0521(6) 0.0201(13) Uani 1 1 d . . . . .
H2 H 0.341258 0.634585 0.020657 0.024 Uiso 1 1 calc R . . . .
C3 C 0.4378(7) 0.7705(6) 0.4400(6) 0.0178(12) Uani 1 1 d . . . . .
C4 C 0.2936(7) 0.9266(6) 0.4284(6) 0.0166(12) Uani 1 1 d . . . . .
H4 H 0.188774 0.927848 0.434798 0.020 Uiso 1 1 calc R . . . .
C5 C 0.3054(7) 1.0635(6) 0.4095(6) 0.0152(12) Uani 1 1 d . . . . .
H5 H 0.412842 1.062212 0.395579 0.018 Uiso 1 1 calc R . . . .
C6 C 0.1514(7) 1.2214(6) 0.4098(6) 0.0147(12) Uani 1 1 d . . . . .
O9 O 0.0731(5) 0.2206(5) 0.9548(4) 0.0285(10) Uani 1 1 d . . . . .
O10 O 0.2245(6) -0.0321(6) 0.8383(5) 0.0406(12) Uani 1 1 d D . . . .
H10 H 0.132(6) 0.001(9) 0.826(8) 0.07(3) Uiso 1 1 d D . . . .
C7 C 0.2046(8) 0.0866(7) 0.9185(6) 0.0248(13) Uani 1 1 d . . . . .
C8 C 0.3570(7) 0.0416(7) 0.9600(6) 0.0185(12) Uani 1 1 d . . . . .
C9 C 0.3633(7) 0.1591(7) 1.0306(6) 0.0234(13) Uani 1 1 d . . . . .
H9 H 0.272425 0.265870 1.050903 0.028 Uiso 1 1 calc R . . . .
C10 C 0.5041(7) 0.1181(7) 1.0708(6) 0.0240(13) Uani 1 1 d . . . . .
H10A H 0.506782 0.197482 1.119004 0.029 Uiso 1 1 calc R . . . .
O11 O -0.0493(6) 0.0376(6) 0.7789(5) 0.0315(10) Uani 1 1 d D . . . .
H11A H -0.090(12) 0.129(4) 0.749(9) 0.11(4) Uiso 1 1 d D . . . .
H11B H -0.058(7) -0.029(4) 0.736(5) 0.012(15) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Tb1 O1 2.516(4) . ?
Tb1 O2 2.510(3) . ?
Tb1 O3 2.343(4) . ?
Tb1 O3 2.906(4) 2_666 ?
Tb1 O4 2.398(4) 2_666 ?
Tb1 O5 2.426(3) 2_576 ?
Tb1 O6 2.379(4) 1_545 ?
Tb1 O7 2.408(4) . ?
Tb1 O8 2.396(4) . ?
O1 C1 1.249(6) . ?
O2 C1 1.276(6) . ?
O3 C3 1.257(6) . ?
O4 C3 1.252(6) . ?
O5 C6 1.259(6) . ?
O6 C6 1.263(6) . ?
O7 H7A 0.840(10) . ?
O7 H7B 0.838(10) . ?
O8 H8A 0.840(10) . ?
O8 H8B 0.837(10) . ?
C1 C2 1.484(7) . ?
C2 C2 1.310(10) 2_665 ?
C2 H2 0.9300 . ?
C3 C4 1.484(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.317(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.499(7) . ?
O9 C7 1.221(7) . ?
O10 H10 0.820(10) . ?
O10 C7 1.319(7) . ?
C7 C8 1.478(7) . ?
C8 C9 1.386(7) . ?
C8 C10 1.400(7) 2_657 ?
C9 H9 0.9300 . ?
C9 C10 1.377(7) . ?
C10 H10A 0.9300 . ?
O11 H11A 0.837(10) . ?
O11 H11B 0.834(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Tb1 O3 69.48(11) . 2_666 ?
O2 Tb1 O1 51.80(11) . . ?
O2 Tb1 O3 115.60(11) . 2_666 ?
O3 Tb1 O1 71.79(13) . . ?
O3 Tb1 O2 76.73(13) . . ?
O3 Tb1 O3 60.61(15) . 2_666 ?
O3 Tb1 O4 108.04(14) . 2_666 ?
O3 Tb1 O5 84.40(13) . 2_576 ?
O3 Tb1 O6 144.87(14) . 1_545 ?
O3 Tb1 O7 140.25(14) . . ?
O3 Tb1 O8 72.53(15) . . ?
O4 Tb1 O1 85.94(13) 2_666 . ?
O4 Tb1 O2 134.66(12) 2_666 . ?
O4 Tb1 O3 47.52(12) 2_666 2_666 ?
O4 Tb1 O5 152.89(13) 2_666 2_576 ?
O4 Tb1 O7 75.30(14) 2_666 . ?
O5 Tb1 O1 121.11(12) 2_576 . ?
O5 Tb1 O2 70.86(12) 2_576 . ?
O5 Tb1 O3 139.33(12) 2_576 2_666 ?
O6 Tb1 O1 74.44(12) 1_545 . ?
O6 Tb1 O2 75.01(12) 1_545 . ?
O6 Tb1 O3 115.22(12) 1_545 2_666 ?
O6 Tb1 O4 78.64(13) 1_545 2_666 ?
O6 Tb1 O5 105.30(13) 1_545 2_576 ?
O6 Tb1 O7 74.81(14) 1_545 . ?
O6 Tb1 O8 142.16(15) 1_545 . ?
O7 Tb1 O1 146.51(13) . . ?
O7 Tb1 O2 129.94(13) . . ?
O7 Tb1 O3 113.14(13) . 2_666 ?
O7 Tb1 O5 79.88(13) . 2_576 ?
O8 Tb1 O1 137.22(13) . . ?
O8 Tb1 O2 137.49(14) . . ?
O8 Tb1 O3 72.86(13) . 2_666 ?
O8 Tb1 O4 83.35(15) . 2_666 ?
O8 Tb1 O5 77.51(14) . 2_576 ?
O8 Tb1 O7 68.52(15) . . ?
C1 O1 Tb1 93.9(3) . . ?
C1 O2 Tb1 93.5(3) . . ?
Tb1 O3 Tb1 119.39(15) . 2_666 ?
C3 O3 Tb1 83.2(3) . 2_666 ?
C3 O3 Tb1 157.3(4) . . ?
C3 O4 Tb1 107.9(3) . 2_666 ?
C6 O5 Tb1 110.3(3) . 2_576 ?
C6 O6 Tb1 154.4(3) . 1_565 ?
Tb1 O7 H7A 108(4) . . ?
Tb1 O7 H7B 115(5) . . ?
H7A O7 H7B 115(3) . . ?
Tb1 O8 H8A 118(4) . . ?
Tb1 O8 H8B 132(5) . . ?
H8A O8 H8B 106(6) . . ?
O1 C1 O2 120.8(5) . . ?
O1 C1 C2 121.2(5) . . ?
O2 C1 C2 117.9(5) . . ?
C1 C2 H2 117.7 . . ?
C2 C2 C1 124.5(7) 2_665 . ?
C2 C2 H2 117.7 2_665 . ?
O3 C3 Tb1 72.4(3) . 2_666 ?
O3 C3 C4 118.0(5) . . ?
O4 C3 Tb1 48.9(3) . 2_666 ?
O4 C3 O3 121.3(5) . . ?
O4 C3 C4 120.7(5) . . ?
C4 C3 Tb1 169.3(4) . 2_666 ?
C3 C4 H4 118.1 . . ?
C5 C4 C3 123.8(5) . . ?
C5 C4 H4 118.1 . . ?
C4 C5 H5 118.9 . . ?
C4 C5 C6 122.2(5) . . ?
C6 C5 H5 118.9 . . ?
O5 C6 O6 122.4(5) . . ?
O5 C6 C5 119.9(5) . . ?
O6 C6 C5 117.7(5) . . ?
C7 O10 H10 107(6) . . ?
O9 C7 O10 123.3(6) . . ?
O9 C7 C8 123.3(5) . . ?
O10 C7 C8 113.4(5) . . ?
C9 C8 C7 119.7(5) . . ?
C9 C8 C10 119.1(5) . 2_657 ?
C10 C8 C7 121.2(5) 2_657 . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.1(5) . . ?
C10 C9 H9 119.9 . . ?
C8 C10 H10A 119.6 2_657 . ?
C9 C10 C8 120.8(5) . 2_657 ?
C9 C10 H10A 119.6 . . ?
H11A O11 H11B 111(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
O7 H7A O2 0.840(10) 1.991(19) 2.815(5) 167(6) 2_566
O7 H7B O9 0.838(10) 2.04(3) 2.792(5) 149(5) .
O8 H8A O1 0.840(10) 1.93(2) 2.749(6) 165(6) 2_666
O8 H8B O9 0.837(10) 2.009(14) 2.844(6) 175(7) 2_567
O10 H10 O11 0.820(10) 1.773(18) 2.584(6) 170(8) .
O11 H11A O2 0.837(10) 2.064(13) 2.900(6) 175(8) 2_566
O11 H11B O5 0.834(10) 2.095(15) 2.917(6) 169(5) 2_566

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
Tb1 O1 C1 O2 -0.9(5) . . . . ?
Tb1 O1 C1 C2 -179.5(4) . . . . ?
Tb1 O2 C1 O1 0.9(5) . . . . ?
Tb1 O2 C1 C2 179.5(4) . . . . ?
Tb1 O3 C3 Tb1 -174.5(9) . . . 2_666 ?
Tb1 O3 C3 O4 2.5(5) 2_666 . . . ?
Tb1 O3 C3 O4 -171.9(6) . . . . ?
Tb1 O3 C3 C4 -177.2(4) 2_666 . . . ?
Tb1 O3 C3 C4 8.3(13) . . . . ?
Tb1 O4 C3 O3 -3.2(6) 2_666 . . . ?
Tb1 O4 C3 C4 176.5(4) 2_666 . . . ?
Tb1 O5 C6 O6 -13.9(6) 2_576 . . . ?
Tb1 O5 C6 C5 164.7(4) 2_576 . . . ?
Tb1 O6 C6 O5 154.5(6) 1_565 . . . ?
Tb1 O6 C6 C5 -24.1(11) 1_565 . . . ?
Tb1 C3 C4 C5 5(2) 2_666 . . . ?
O1 C1 C2 C2 -0.2(10) . . . 2_665 ?
O2 C1 C2 C2 -178.9(7) . . . 2_665 ?
O3 C3 C4 C5 170.3(5) . . . . ?
O4 C3 C4 C5 -9.5(8) . . . . ?
C3 C4 C5 C6 -175.4(4) . . . . ?
C4 C5 C6 O5 -19.4(8) . . . . ?
C4 C5 C6 O6 159.3(5) . . . . ?
O9 C7 C8 C9 -6.7(9) . . . . ?
O9 C7 C8 C10 173.4(5) . . . 2_657 ?
O10 C7 C8 C9 173.3(5) . . . . ?
O10 C7 C8 C10 -6.6(8) . . . 2_657 ?
C7 C8 C9 C10 179.5(5) . . . . ?
C8 C9 C10 C8 0.6(9) . . . 2_657 ?
C10 C8 C9 C10 -0.6(9) 2_657 . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_6er
_database_code_depnum_ccdc_archive 'CCDC 1863669'
_audit_update_record             
;
2018-08-24 deposited with the CCDC.
2018-09-26 downloaded from the CCDC.
;
_audit_creation_date             2018-03-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H16 Er2 O16, 2(H2 O)'
_chemical_formula_sum            'C16 H20 Er2 O18'
_chemical_formula_weight         834.84
_chemical_absolute_configuration unk
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Er Er -0.2586 4.9576 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.9118(2)
_cell_length_b                   12.3451(3)
_cell_length_c                   10.3400(2)
_cell_angle_alpha                90
_cell_angle_beta                 103.0475(9)
_cell_angle_gamma                90
_cell_volume                     1108.21(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9665
_cell_measurement_temperature    296
_cell_measurement_theta_max      30.521
_cell_measurement_theta_min      3.190
_shelx_estimated_absorpt_T_max   0.581
_shelx_estimated_absorpt_T_min   0.376
_exptl_absorpt_coefficient_mu    7.613
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6301
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0799 before and 0.0588 after correction. The Ratio of minimum to maximum transmission is 0.8445. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light pink'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    pink
_exptl_crystal_density_diffrn    2.502
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            34355
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.539
_diffrn_reflns_theta_min         3.190
_diffrn_ambient_temperature      296.0
_diffrn_detector                 'Bruker PHOTON 100 area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'PHOTON area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'four-circle KAPPA diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_collimation    '0.5 mm'
_diffrn_radiation_monochromator  'graphiteDouble Bounce Multilayer Mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed x-ray tube'
_diffrn_source_target            Cu
_diffrn_source_type              'Incoatec I\mus'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.917
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                6323
_reflns_number_total             6761
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2016)'
_computing_data_collection       'APEX 3 (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'

_refine_diff_density_max         0.583
_refine_diff_density_min         -0.671
_refine_diff_density_rms         0.128
_refine_ls_abs_structure_details 
;
 Flack x determined using 2857 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.002(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     373
_refine_ls_number_reflns         6761
_refine_ls_number_restraints     19
_refine_ls_R_factor_all          0.0257
_refine_ls_R_factor_gt           0.0209
_refine_ls_restrained_S_all      1.003
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0084P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0318
_refine_ls_wR_factor_ref         0.0326
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 O14-H14A = O16-H16A
 0.84 with sigma of 0.01
 O14-H14B
 0.84 with sigma of 0.01
 H14A-H14B
 1.37 with sigma of 0.02
 O17-H17A
 0.84 with sigma of 0.01
 O16-H16B
 0.84 with sigma of 0.01
 H16A-H16B
 1.355 with sigma of 0.02
 O17-H17B
 0.84 with sigma of 0.01
 H17A-H17B
 1.35 with sigma of 0.02
 O15-H15A
 0.84 with sigma of 0.01
 O15-H15B
 0.84 with sigma of 0.01
 H15B-H15A
 1.37 with sigma of 0.02
 O18-H18A
 0.84 with sigma of 0.01
 O18-H18B
 0.84 with sigma of 0.01
 H18A-H18B
 1.39 with sigma of 0.02
 O13-H13B = O13-H13A
 0.84 with sigma of 0.01
 H13B-H13A
 1.39 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C10(H10), C11(H11), C14(H14), C15(H15)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.38205(2) 0.59007(2) 0.67819(2) 0.01233(5) Uani 1 1 d . . . . .
Er2 Er 0.07138(2) 0.50508(2) 0.88152(2) 0.01168(5) Uani 1 1 d . . . . .
O1 O 0.4368(5) 0.6204(3) 0.4652(4) 0.0359(11) Uani 1 1 d . . . . .
O2 O 0.5969(4) 0.5124(4) 0.5913(3) 0.0308(8) Uani 1 1 d . . . . .
O3 O 0.8570(4) 0.5715(3) -0.0346(3) 0.0295(9) Uani 1 1 d . . . . .
O4 O 1.0389(5) 0.4859(4) 0.1065(4) 0.0450(13) Uani 1 1 d . . . . .
O5 O 0.1352(4) 0.6516(3) 0.5785(3) 0.0208(8) Uani 1 1 d . . . . .
O6 O -0.0223(4) 0.6270(3) 0.7166(3) 0.0210(8) Uani 1 1 d . . . . .
O7 O -0.1802(4) 0.9457(3) 0.2850(3) 0.0185(7) Uani 1 1 d . . . . .
O8 O -0.2819(5) 0.9356(3) 0.4563(4) 0.0308(10) Uani 1 1 d . . . . .
O9 O 0.4854(4) 0.4751(3) 0.8510(3) 0.0206(8) Uani 1 1 d . . . . .
O10 O 0.3208(4) 0.4562(3) 0.9857(4) 0.0234(8) Uani 1 1 d . . . . .
O11 O 0.8534(5) 0.1721(3) 1.0084(4) 0.0357(10) Uani 1 1 d . . . . .
O12 O 0.7051(4) 0.1627(3) 1.1491(3) 0.0227(8) Uani 1 1 d . . . . .
O13 O 0.3870(6) 0.7835(4) 0.6356(6) 0.0485(12) Uani 1 1 d D . . . .
H13A H 0.369(12) 0.790(10) 0.5527(17) 0.19(7) Uiso 1 1 d D . . . .
H13B H 0.464(7) 0.821(6) 0.671(7) 0.09(3) Uiso 1 1 d D . . . .
O14 O 0.6198(4) 0.6693(4) 0.7945(4) 0.0310(9) Uani 1 1 d D . . . .
H14A H 0.691(6) 0.630(6) 0.836(8) 0.11(4) Uiso 1 1 d D . . . .
H14B H 0.655(7) 0.717(4) 0.752(6) 0.06(2) Uiso 1 1 d D . . . .
O15 O 0.0749(6) 0.3137(3) 0.9309(5) 0.0390(10) Uani 1 1 d D . . . .
H15A H 0.002(7) 0.297(7) 0.966(9) 0.12(4) Uiso 1 1 d D . . . .
H15B H 0.144(8) 0.267(6) 0.952(11) 0.14(5) Uiso 1 1 d D . . . .
O16 O -0.1474(4) 0.4210(3) 0.7509(4) 0.0265(8) Uani 1 1 d D . . . .
H16A H -0.213(4) 0.458(3) 0.700(4) 0.020(14) Uiso 1 1 d D . . . .
H16B H -0.165(8) 0.3560(16) 0.729(7) 0.07(3) Uiso 1 1 d D . . . .
C1 C 0.6520(6) 0.5611(4) 0.3812(6) 0.0251(13) Uani 1 1 d . . . . .
C2 C 0.5970(7) 0.6085(5) 0.2580(6) 0.0330(15) Uani 1 1 d . . . . .
H2 H 0.503225 0.644840 0.240363 0.040 Uiso 1 1 calc R . . . .
C3 C 0.6821(6) 0.6016(6) 0.1606(5) 0.0337(14) Uani 1 1 d . . . . .
H3 H 0.645011 0.632962 0.077817 0.040 Uiso 1 1 calc R . . . .
C4 C 0.8214(6) 0.5480(4) 0.1875(5) 0.0231(11) Uani 1 1 d . . . . .
C5 C 0.8777(6) 0.5043(6) 0.3092(5) 0.0307(12) Uani 1 1 d . . . . .
H5 H 0.973240 0.470281 0.327556 0.037 Uiso 1 1 calc R . . . .
C6 C 0.7925(6) 0.5103(5) 0.4074(5) 0.0267(11) Uani 1 1 d . . . . .
H6 H 0.831168 0.479855 0.490499 0.032 Uiso 1 1 calc R . . . .
C7 C 0.5571(6) 0.5642(4) 0.4853(5) 0.0223(12) Uani 1 1 d . . . . .
C8 C 0.9095(6) 0.5344(4) 0.0799(6) 0.0216(12) Uani 1 1 d . . . . .
C9 C 0.0160(5) 0.6716(4) 0.6197(5) 0.0170(9) Uani 1 1 d . . . . .
C10 C -0.0906(6) 0.7577(4) 0.5541(5) 0.0245(11) Uani 1 1 d . . . . .
H10 H -0.170108 0.776704 0.594509 0.029 Uiso 1 1 calc R . . . .
C11 C -0.0843(6) 0.8094(4) 0.4456(5) 0.0212(10) Uani 1 1 d . . . . .
H11 H -0.011465 0.788090 0.398903 0.025 Uiso 1 1 calc R . . . .
C12 C -0.1882(6) 0.9006(4) 0.3937(5) 0.0179(10) Uani 1 1 d . . . . .
C13 C 0.4416(5) 0.4328(4) 0.9464(5) 0.0173(9) Uani 1 1 d . . . . .
C14 C 0.5370(5) 0.3445(4) 1.0213(5) 0.0222(11) Uani 1 1 d . . . . .
H14 H 0.508520 0.316728 1.095899 0.027 Uiso 1 1 calc R . . . .
C15 C 0.6575(6) 0.3039(4) 0.9886(5) 0.0231(11) Uani 1 1 d . . . . .
H15 H 0.692747 0.336719 0.920071 0.028 Uiso 1 1 calc R . . . .
C16 C 0.7424(6) 0.2080(4) 1.0543(5) 0.0199(10) Uani 1 1 d . . . . .
O17 O 0.6670(5) 0.8886(4) 0.7171(5) 0.0415(11) Uani 1 1 d D . . . .
H17A H 0.694(10) 0.926(6) 0.659(5) 0.09(3) Uiso 1 1 d D . . . .
H17B H 0.705(7) 0.917(5) 0.790(3) 0.05(2) Uiso 1 1 d D . . . .
O18 O -0.1918(7) 0.2062(4) 0.7208(5) 0.0537(13) Uani 1 1 d D . . . .
H18A H -0.179(9) 0.178(6) 0.796(3) 0.08(3) Uiso 1 1 d D . . . .
H18B H -0.263(6) 0.176(6) 0.666(5) 0.06(3) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Er1 O1 2.391(4) . ?
Er1 O2 2.484(3) . ?
Er1 O5 2.336(3) . ?
Er1 O7 2.621(3) 2_546 ?
Er1 O8 2.409(4) 2_546 ?
Er1 O9 2.305(3) . ?
Er1 O12 2.286(3) 2_657 ?
Er1 O13 2.430(4) . ?
Er1 O14 2.397(4) . ?
Er2 O3 2.413(3) 1_456 ?
Er2 O4 2.420(3) 1_456 ?
Er2 O6 2.286(3) . ?
Er2 O7 2.279(3) 2_546 ?
Er2 O10 2.321(4) . ?
Er2 O11 2.377(4) 2_657 ?
Er2 O12 2.854(4) 2_657 ?
Er2 O15 2.416(4) . ?
Er2 O16 2.349(4) . ?
O1 C7 1.254(6) . ?
O2 C7 1.250(6) . ?
O3 C8 1.257(6) . ?
O4 C8 1.273(6) . ?
O5 C9 1.255(6) . ?
O6 C9 1.256(6) . ?
O7 C12 1.271(6) . ?
O8 C12 1.244(6) . ?
O9 C13 1.254(6) . ?
O10 C13 1.267(6) . ?
O11 C16 1.270(6) . ?
O12 C16 1.237(6) . ?
O13 H13A 0.839(14) . ?
O13 H13B 0.840(15) . ?
O14 H14A 0.836(14) . ?
O14 H14B 0.836(14) . ?
O15 H15A 0.840(14) . ?
O15 H15B 0.838(14) . ?
O16 H16A 0.835(14) . ?
O16 H16B 0.839(14) . ?
C1 C2 1.387(8) . ?
C1 C6 1.371(7) . ?
C1 C7 1.512(7) . ?
C2 H2 0.9300 . ?
C2 C3 1.393(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.379(8) . ?
C4 C5 1.357(8) . ?
C4 C8 1.509(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.400(6) . ?
C6 H6 0.9300 . ?
C9 C10 1.484(7) . ?
C10 H10 0.9300 . ?
C10 C11 1.303(7) . ?
C11 H11 0.9300 . ?
C11 C12 1.479(7) . ?
C13 C14 1.487(7) . ?
C14 H14 0.9300 . ?
C14 C15 1.298(7) . ?
C15 H15 0.9300 . ?
C15 C16 1.484(7) . ?
O17 H17A 0.835(14) . ?
O17 H17B 0.832(14) . ?
O18 H18A 0.838(14) . ?
O18 H18B 0.838(14) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Er1 O2 52.61(13) . . ?
O1 Er1 O7 122.01(14) . 2_546 ?
O1 Er1 O8 73.63(14) . 2_546 ?
O1 Er1 O13 70.34(17) . . ?
O1 Er1 O14 93.28(15) . . ?
O2 Er1 O7 113.62(13) . 2_546 ?
O5 Er1 O1 84.85(13) . . ?
O5 Er1 O2 133.79(11) . . ?
O5 Er1 O7 71.11(12) . 2_546 ?
O5 Er1 O8 79.24(14) . 2_546 ?
O5 Er1 O13 69.77(15) . . ?
O5 Er1 O14 136.62(15) . . ?
O8 Er1 O2 72.62(14) 2_546 . ?
O8 Er1 O7 50.85(11) 2_546 2_546 ?
O8 Er1 O13 133.82(17) 2_546 . ?
O9 Er1 O1 132.97(12) . . ?
O9 Er1 O2 80.62(12) . . ?
O9 Er1 O5 135.58(11) . . ?
O9 Er1 O7 68.65(11) . 2_546 ?
O9 Er1 O8 89.50(14) . 2_546 ?
O9 Er1 O13 136.47(16) . . ?
O9 Er1 O14 73.07(14) . . ?
O12 Er1 O1 146.58(13) 2_657 . ?
O12 Er1 O2 149.28(12) 2_657 . ?
O12 Er1 O5 76.42(12) 2_657 . ?
O12 Er1 O7 77.76(12) 2_657 2_546 ?
O12 Er1 O8 127.94(12) 2_657 2_546 ?
O12 Er1 O9 77.44(13) 2_657 . ?
O12 Er1 O13 77.24(17) 2_657 . ?
O12 Er1 O14 82.26(14) 2_657 . ?
O13 Er1 O2 105.47(18) . . ?
O13 Er1 O7 137.37(15) . 2_546 ?
O14 Er1 O2 70.88(14) . . ?
O14 Er1 O7 139.72(13) . 2_546 ?
O14 Er1 O8 141.54(14) . 2_546 ?
O14 Er1 O13 68.88(17) . . ?
O3 Er2 O4 53.96(13) 1_456 1_456 ?
O3 Er2 O12 115.93(12) 1_456 2_657 ?
O3 Er2 O15 103.30(16) 1_456 . ?
O4 Er2 O12 114.28(15) 1_456 2_657 ?
O6 Er2 O3 81.89(12) . 1_456 ?
O6 Er2 O4 132.75(13) . 1_456 ?
O6 Er2 O10 131.87(12) . . ?
O6 Er2 O11 78.59(14) . 2_657 ?
O6 Er2 O12 67.34(11) . 2_657 ?
O6 Er2 O15 141.86(15) . . ?
O6 Er2 O16 75.28(13) . . ?
O7 Er2 O3 152.51(12) 2_546 1_456 ?
O7 Er2 O4 149.11(13) 2_546 1_456 ?
O7 Er2 O6 78.14(12) 2_546 . ?
O7 Er2 O10 74.96(12) 2_546 . ?
O7 Er2 O11 121.24(12) 2_546 2_657 ?
O7 Er2 O12 73.09(10) 2_546 2_657 ?
O7 Er2 O15 81.80(16) 2_546 . ?
O7 Er2 O16 82.11(13) 2_546 . ?
O10 Er2 O3 132.45(12) . 1_456 ?
O10 Er2 O4 80.69(13) . 1_456 ?
O10 Er2 O11 82.31(15) . 2_657 ?
O10 Er2 O12 66.99(12) . 2_657 ?
O10 Er2 O15 71.47(14) . . ?
O10 Er2 O16 137.40(14) . . ?
O11 Er2 O3 72.17(13) 2_657 1_456 ?
O11 Er2 O4 72.94(16) 2_657 1_456 ?
O11 Er2 O12 48.16(11) 2_657 2_657 ?
O11 Er2 O15 139.31(17) 2_657 . ?
O15 Er2 O4 72.53(17) . 1_456 ?
O15 Er2 O12 135.59(14) . 2_657 ?
O16 Er2 O3 74.63(14) . 1_456 ?
O16 Er2 O4 104.24(16) . 1_456 ?
O16 Er2 O11 140.05(15) . 2_657 ?
O16 Er2 O12 138.38(12) . 2_657 ?
O16 Er2 O15 70.05(15) . . ?
C7 O1 Er1 96.1(3) . . ?
C7 O2 Er1 91.7(3) . . ?
C8 O3 Er2 93.3(3) . 1_654 ?
C8 O4 Er2 92.6(3) . 1_654 ?
C9 O5 Er1 134.3(3) . . ?
C9 O6 Er2 139.9(3) . . ?
Er2 O7 Er1 108.29(12) 2_556 2_556 ?
C12 O7 Er1 89.5(3) . 2_556 ?
C12 O7 Er2 158.0(3) . 2_556 ?
C12 O8 Er1 100.4(3) . 2_556 ?
C13 O9 Er1 136.5(3) . . ?
C13 O10 Er2 134.8(3) . . ?
C16 O11 Er2 106.5(3) . 2_647 ?
Er1 O12 Er2 100.82(12) 2_647 2_647 ?
C16 O12 Er1 174.8(4) . 2_647 ?
C16 O12 Er2 84.3(3) . 2_647 ?
Er1 O13 H13A 106(9) . . ?
Er1 O13 H13B 121(6) . . ?
H13A O13 H13B 110(4) . . ?
Er1 O14 H14A 120(6) . . ?
Er1 O14 H14B 114(5) . . ?
H14A O14 H14B 110(4) . . ?
Er2 O15 H15A 111(6) . . ?
Er2 O15 H15B 135(7) . . ?
H15A O15 H15B 109(4) . . ?
Er2 O16 H16A 120(3) . . ?
Er2 O16 H16B 131(4) . . ?
H16A O16 H16B 107(3) . . ?
C2 C1 C7 120.3(5) . . ?
C6 C1 C2 119.5(5) . . ?
C6 C1 C7 120.2(5) . . ?
C1 C2 H2 120.0 . . ?
C1 C2 C3 120.1(5) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.7(5) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 C8 119.9(5) . . ?
C5 C4 C3 120.3(5) . . ?
C5 C4 C8 119.7(5) . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.3(5) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 120.1(5) . . ?
C1 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
O1 C7 C1 119.4(5) . . ?
O2 C7 O1 119.4(4) . . ?
O2 C7 C1 121.2(5) . . ?
O3 C8 Er2 59.9(3) . 1_654 ?
O3 C8 O4 120.1(5) . . ?
O3 C8 C4 120.6(5) . . ?
O4 C8 Er2 60.2(3) . 1_654 ?
O4 C8 C4 119.3(5) . . ?
C4 C8 Er2 178.9(3) . 1_654 ?
O5 C9 O6 126.0(5) . . ?
O5 C9 C10 119.3(4) . . ?
O6 C9 C10 114.7(4) . . ?
C9 C10 H10 116.7 . . ?
C11 C10 C9 126.6(5) . . ?
C11 C10 H10 116.7 . . ?
C10 C11 H11 118.7 . . ?
C10 C11 C12 122.7(5) . . ?
C12 C11 H11 118.7 . . ?
O7 C12 Er1 64.5(3) . 2_556 ?
O7 C12 C11 119.9(4) . . ?
O8 C12 Er1 54.7(3) . 2_556 ?
O8 C12 O7 119.1(5) . . ?
O8 C12 C11 121.0(5) . . ?
C11 C12 Er1 173.5(4) . 2_556 ?
O9 C13 O10 126.5(4) . . ?
O9 C13 C14 118.2(4) . . ?
O10 C13 C14 115.3(4) . . ?
C13 C14 H14 118.1 . . ?
C15 C14 C13 123.8(5) . . ?
C15 C14 H14 118.1 . . ?
C14 C15 H15 118.2 . . ?
C14 C15 C16 123.7(5) . . ?
C16 C15 H15 118.2 . . ?
O11 C16 Er2 49.6(2) . 2_647 ?
O11 C16 C15 117.8(4) . . ?
O12 C16 Er2 71.4(3) . 2_647 ?
O12 C16 O11 120.6(5) . . ?
O12 C16 C15 121.5(5) . . ?
C15 C16 Er2 165.4(3) . 2_647 ?
H17A O17 H17B 107(4) . . ?
H18A O18 H18B 112(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
O13 H13B O17 0.840(15) 1.95(3) 2.771(7) 164(9) .
O14 H14A O3 0.836(14) 1.90(3) 2.713(6) 164(10) 1_556
O14 H14B O17 0.836(14) 2.16(4) 2.881(6) 145(7) .
O15 H15A O11 0.840(14) 2.14(6) 2.883(6) 147(9) 1_455
O15 H15B O3 0.838(14) 2.56(7) 3.188(6) 133(8) 2_646
O16 H16A O2 0.835(14) 1.92(2) 2.737(5) 164(5) 1_455
O16 H16B O18 0.839(14) 1.86(2) 2.689(6) 167(7) .
O17 H17A O8 0.835(14) 2.16(4) 2.893(6) 147(7) 1_655
O17 H17B O4 0.832(14) 2.44(5) 3.079(6) 134(6) 2_756
O17 H17B O10 0.832(14) 2.43(4) 3.163(6) 148(6) 2_657
O18 H18A O11 0.838(14) 2.15(3) 2.940(6) 157(8) 1_455
O18 H18B O1 0.838(14) 1.939(17) 2.773(7) 174(8) 2_546

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
Er1 O1 C7 O2 4.3(6) . . . . ?
Er1 O1 C7 C1 -175.2(4) . . . . ?
Er1 O2 C7 O1 -4.1(5) . . . . ?
Er1 O2 C7 C1 175.4(4) . . . . ?
Er1 O5 C9 O6 -28.9(8) . . . . ?
Er1 O5 C9 C10 149.0(4) . . . . ?
Er1 O7 C12 O8 4.0(5) 2_556 . . . ?
Er1 O7 C12 C11 -174.6(4) 2_556 . . . ?
Er1 O8 C12 O7 -4.4(5) 2_556 . . . ?
Er1 O8 C12 C11 174.2(4) 2_556 . . . ?
Er1 O9 C13 O10 -10.6(8) . . . . ?
Er1 O9 C13 C14 168.1(3) . . . . ?
Er2 O3 C8 O4 1.9(6) 1_654 . . . ?
Er2 O3 C8 C4 -178.9(4) 1_654 . . . ?
Er2 O4 C8 O3 -1.9(6) 1_654 . . . ?
Er2 O4 C8 C4 178.9(4) 1_654 . . . ?
Er2 O6 C9 O5 4.9(9) . . . . ?
Er2 O6 C9 C10 -173.1(4) . . . . ?
Er2 O7 C12 Er1 145.0(9) 2_556 . . 2_556 ?
Er2 O7 C12 O8 149.0(7) 2_556 . . . ?
Er2 O7 C12 C11 -29.6(11) 2_556 . . . ?
Er2 O10 C13 O9 36.7(8) . . . . ?
Er2 O10 C13 C14 -142.0(4) . . . . ?
Er2 O11 C16 O12 7.3(6) 2_647 . . . ?
Er2 O11 C16 C15 -171.2(4) 2_647 . . . ?
Er2 O12 C16 O11 -5.9(5) 2_647 . . . ?
Er2 O12 C16 C15 172.6(5) 2_647 . . . ?
O5 C9 C10 C11 8.2(9) . . . . ?
O6 C9 C10 C11 -173.7(6) . . . . ?
O9 C13 C14 C15 -4.6(8) . . . . ?
O10 C13 C14 C15 174.3(5) . . . . ?
C1 C2 C3 C4 -0.3(10) . . . . ?
C2 C1 C6 C5 -1.5(9) . . . . ?
C2 C1 C7 O1 -8.1(7) . . . . ?
C2 C1 C7 O2 172.3(6) . . . . ?
C2 C3 C4 C5 -1.6(10) . . . . ?
C2 C3 C4 C8 176.3(5) . . . . ?
C3 C4 C5 C6 2.0(10) . . . . ?
C3 C4 C8 O3 0.0(8) . . . . ?
C3 C4 C8 O4 179.2(6) . . . . ?
C4 C5 C6 C1 -0.5(10) . . . . ?
C5 C4 C8 O3 177.9(6) . . . . ?
C5 C4 C8 O4 -2.9(8) . . . . ?
C6 C1 C2 C3 1.8(9) . . . . ?
C6 C1 C7 O1 172.6(5) . . . . ?
C6 C1 C7 O2 -6.9(8) . . . . ?
C7 C1 C2 C3 -177.4(6) . . . . ?
C7 C1 C6 C5 177.8(6) . . . . ?
C8 C4 C5 C6 -175.9(5) . . . . ?
C9 C10 C11 C12 -174.7(5) . . . . ?
C10 C11 C12 O7 -177.6(5) . . . . ?
C10 C11 C12 O8 3.8(8) . . . . ?
C13 C14 C15 C16 -173.1(5) . . . . ?
C14 C15 C16 Er2 148.3(12) . . . 2_647 ?
C14 C15 C16 O11 176.0(5) . . . . ?
C14 C15 C16 O12 -2.5(9) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_8
_database_code_depnum_ccdc_archive 'CCDC 1863671'
_audit_update_record             
;
2018-08-24 deposited with the CCDC.
2018-09-26 downloaded from the CCDC.
;
_audit_creation_date             2018-04-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.18 svn.r3501 for OlexSys, GUI svn.r5488)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C10 H5 Eu O6'
_chemical_formula_sum            'C10 H5 Eu O6'
_chemical_formula_weight         373.10
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Eu Eu -0.1578 3.6682 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 '-x, y+1/2, -z+1/2'
4 'x+1/2, -y+1/2, -z'
5 '-x, -y, -z'
6 'x-1/2, y, -z-1/2'
7 'x, -y-1/2, z-1/2'
8 '-x-1/2, y-1/2, z'

_cell_length_a                   14.0967(8)
_cell_length_b                   6.8258(3)
_cell_length_c                   22.0196(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2118.8(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6598
_cell_measurement_temperature    296
_cell_measurement_theta_max      26.986
_cell_measurement_theta_min      2.35
_exptl_absorpt_coefficient_mu    5.933
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6764
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0792 before and 0.0663 after correction. The Ratio of minimum to maximum transmission is 0.9073. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.339
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0849
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            28005
_diffrn_reflns_theta_full        27.15
_diffrn_reflns_theta_max         27.15
_diffrn_reflns_theta_min         1.85
_diffrn_ambient_temperature      296.0
_diffrn_detector                 'Bruker PHOTON 100 area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'PHOTON area detector'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'four-circle KAPPA diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_collimation    '0.5 mm'
_diffrn_radiation_monochromator  'graphiteDouble Bounce Multilayer Mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed x-ray tube'
_diffrn_source_type              'Incoatec I\mus'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                1761
_reflns_number_total             2326
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2016)'
_computing_data_collection       'APEX 3 (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.875
_refine_diff_density_min         -0.838
_refine_diff_density_rms         0.317
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2326
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0259
_refine_ls_restrained_S_all      1.149
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0443P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0572
_refine_ls_wR_factor_ref         0.0845
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C7(H7), C8(H8)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Eu1 Eu 0.668643(18) 1.05090(4) 0.557235(12) 0.01119(11) Uani 1 d . . .
O1 O 0.6696(3) 0.6949(6) 0.54889(18) 0.0202(10) Uani 1 d . . .
O2 O 0.6715(3) 0.3920(6) 0.51568(19) 0.0183(9) Uani 1 d . . .
O3 O 0.5123(3) 0.9926(6) 0.57243(18) 0.0212(9) Uani 1 d . . .
O4 O 0.3614(3) 0.9973(7) 0.54598(18) 0.0213(10) Uani 1 d . . .
O5 O 0.3743(3) 0.7786(7) 0.86713(19) 0.0313(11) Uani 1 d . . .
O6 O 0.2376(3) 0.9331(6) 0.85317(19) 0.0291(11) Uani 1 d . . .
C1 C 0.6271(4) 0.5489(9) 0.5255(3) 0.0168(12) Uani 1 d . . .
C2 C 0.5257(4) 0.5680(8) 0.5105(3) 0.0280(16) Uani 1 d . . .
H2 H 0.4973 0.6891 0.5170 0.034 Uiso 1 calc . . R
C3 C 0.3970(4) 0.9651(9) 0.6506(3) 0.0174(13) Uani 1 d . . .
C4 C 0.4646(4) 0.9086(10) 0.6931(3) 0.0271(15) Uani 1 d . . .
H4 H 0.5276 0.8917 0.6818 0.033 Uiso 1 calc . . R
C5 C 0.4366(5) 0.8780(10) 0.7526(3) 0.0296(16) Uani 1 d . . .
H5 H 0.4807 0.8346 0.7809 0.036 Uiso 1 calc . . R
C6 C 0.3447(4) 0.9107(9) 0.7703(3) 0.0196(13) Uani 1 d . . .
C7 C 0.2786(5) 0.9741(10) 0.7283(3) 0.0253(15) Uani 1 d . . .
H7 H 0.2167 1.0007 0.7402 0.030 Uiso 1 calc . . R
C8 C 0.3053(4) 0.9973(10) 0.6686(3) 0.0227(14) Uani 1 d . . .
H8 H 0.2603 1.0356 0.6400 0.027 Uiso 1 calc . . R
C9 C 0.4254(4) 0.9874(8) 0.5853(3) 0.0146(12) Uani 1 d . . .
C10 C 0.3167(4) 0.8733(9) 0.8348(3) 0.0225(14) Uani 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Eu1 Eu1 4.1121(3) 8_765 ?
Eu1 Eu1 4.1120(3) 8_755 ?
Eu1 O1 2.437(4) . ?
Eu1 O1 2.490(4) 8_765 ?
Eu1 O2 2.502(4) 1_565 ?
Eu1 O2 2.663(4) 8_765 ?
Eu1 O3 2.264(4) . ?
Eu1 O4 2.335(4) 5_676 ?
Eu1 O5 2.357(4) 3_656 ?
Eu1 O6 2.341(4) 6_657 ?
Eu1 C1 2.963(6) 8_765 ?
Eu1 C10 3.246(6) 3_656 ?
O1 Eu1 2.490(4) 8_755 ?
O1 C1 1.272(7) . ?
O2 Eu1 2.502(4) 1_545 ?
O2 Eu1 2.663(4) 8_755 ?
O2 C1 1.259(7) . ?
O3 C9 1.258(7) . ?
O4 Eu1 2.335(4) 5_676 ?
O4 C9 1.253(7) . ?
O5 Eu1 2.357(4) 3_646 ?
O5 C10 1.259(8) . ?
O6 Eu1 2.341(4) 6_557 ?
O6 C10 1.254(7) . ?
C1 Eu1 2.963(6) 8_755 ?
C1 C2 1.473(8) . ?
C2 C2 1.266(12) 5_666 ?
C2 H2 0.9300 . ?
C3 C4 1.391(8) . ?
C3 C8 1.370(8) . ?
C3 C9 1.501(8) . ?
C4 H4 0.9300 . ?
C4 C5 1.383(9) . ?
C5 H5 0.9300 . ?
C5 C6 1.371(8) . ?
C6 C7 1.383(9) . ?
C6 C10 1.496(8) . ?
C7 H7 0.9300 . ?
C7 C8 1.376(9) . ?
C8 H8 0.9300 . ?
C10 Eu1 3.246(6) 3_646 ?

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
Eu1 Eu1 Eu1 112.193(12) 8_755 8_765 ?
O1 Eu1 Eu1 33.02(9) 8_765 8_765 ?
O1 Eu1 Eu1 33.83(9) . 8_755 ?
O1 Eu1 Eu1 145.54(9) . 8_765 ?
O1 Eu1 Eu1 79.44(9) 8_765 8_755 ?
O1 Eu1 O1 112.51(11) . 8_765 ?
O1 Eu1 O2 64.10(12) . 8_765 ?
O1 Eu1 O2 154.19(14) . 1_565 ?
O1 Eu1 O2 65.85(13) 8_765 1_565 ?
O1 Eu1 O2 50.24(12) 8_765 8_765 ?
O1 Eu1 C1 88.41(14) . 8_765 ?
O1 Eu1 C1 25.10(15) 8_765 8_765 ?
O1 Eu1 C10 74.22(14) 8_765 3_656 ?
O1 Eu1 C10 136.95(14) . 3_656 ?
O2 Eu1 Eu1 35.90(9) 8_765 8_755 ?
O2 Eu1 Eu1 82.31(8) 8_765 8_765 ?
O2 Eu1 Eu1 38.61(9) 1_565 8_765 ?
O2 Eu1 Eu1 139.76(9) 1_565 8_755 ?
O2 Eu1 O2 103.87(12) 1_565 8_765 ?
O2 Eu1 C1 25.14(14) 8_765 8_765 ?
O2 Eu1 C1 84.38(14) 1_565 8_765 ?
O2 Eu1 C10 118.28(14) 8_765 3_656 ?
O2 Eu1 C10 68.66(15) 1_565 3_656 ?
O3 Eu1 Eu1 113.39(11) . 8_755 ?
O3 Eu1 Eu1 133.54(11) . 8_765 ?
O3 Eu1 O1 80.87(14) . . ?
O3 Eu1 O1 166.33(14) . 8_765 ?
O3 Eu1 O2 103.50(14) . 1_565 ?
O3 Eu1 O2 143.39(14) . 8_765 ?
O3 Eu1 O4 86.72(15) . 5_676 ?
O3 Eu1 O5 76.19(16) . 3_656 ?
O3 Eu1 O6 102.65(16) . 6_657 ?
O3 Eu1 C1 168.47(16) . 8_765 ?
O3 Eu1 C10 94.19(15) . 3_656 ?
O4 Eu1 Eu1 89.09(11) 5_676 8_755 ?
O4 Eu1 Eu1 102.59(12) 5_676 8_765 ?
O4 Eu1 O1 77.71(15) 5_676 . ?
O4 Eu1 O1 98.60(14) 5_676 8_765 ?
O4 Eu1 O2 77.18(15) 5_676 1_565 ?
O4 Eu1 O2 76.19(14) 5_676 8_765 ?
O4 Eu1 O5 137.23(16) 5_676 3_656 ?
O4 Eu1 O6 147.87(16) 5_676 6_657 ?
O4 Eu1 C1 86.87(16) 5_676 8_765 ?
O4 Eu1 C10 145.08(16) 5_676 3_656 ?
O5 Eu1 Eu1 66.18(12) 3_656 8_765 ?
O5 Eu1 Eu1 133.67(12) 3_656 8_755 ?
O5 Eu1 O1 91.57(15) 3_656 8_765 ?
O5 Eu1 O1 135.41(15) 3_656 . ?
O5 Eu1 O2 136.79(15) 3_656 8_765 ?
O5 Eu1 O2 69.46(14) 3_656 1_565 ?
O5 Eu1 C1 114.81(17) 3_656 8_765 ?
O5 Eu1 C10 18.56(16) 3_656 3_656 ?
O6 Eu1 Eu1 58.91(11) 6_657 8_755 ?
O6 Eu1 Eu1 93.06(11) 6_657 8_765 ?
O6 Eu1 O1 73.68(14) 6_657 . ?
O6 Eu1 O1 79.49(15) 6_657 8_765 ?
O6 Eu1 O2 78.38(15) 6_657 8_765 ?
O6 Eu1 O2 128.38(14) 6_657 1_565 ?
O6 Eu1 O5 74.79(17) 6_657 3_656 ?
O6 Eu1 C1 78.12(17) 6_657 8_765 ?
O6 Eu1 C10 65.74(16) 6_657 3_656 ?
C1 Eu1 Eu1 56.92(12) 8_765 8_755 ?
C1 Eu1 Eu1 57.44(12) 8_765 8_765 ?
C1 Eu1 C10 96.55(16) 8_765 3_656 ?
C10 Eu1 Eu1 53.26(11) 3_656 8_765 ?
C10 Eu1 Eu1 121.80(11) 3_656 8_755 ?
Eu1 O1 Eu1 113.15(14) . 8_755 ?
C1 O1 Eu1 98.7(3) . 8_755 ?
C1 O1 Eu1 144.0(4) . . ?
Eu1 O2 Eu1 105.49(14) 1_545 8_755 ?
C1 O2 Eu1 90.9(3) . 8_755 ?
C1 O2 Eu1 136.1(4) . 1_545 ?
C9 O3 Eu1 170.4(4) . . ?
C9 O4 Eu1 142.7(4) . 5_676 ?
C10 O5 Eu1 124.9(4) . 3_646 ?
C10 O6 Eu1 138.8(4) . 6_557 ?
O1 C1 Eu1 56.2(3) . 8_755 ?
O1 C1 C2 118.6(5) . . ?
O2 C1 Eu1 64.0(3) . 8_755 ?
O2 C1 O1 120.1(5) . . ?
O2 C1 C2 121.3(5) . . ?
C2 C1 Eu1 174.6(4) . 8_755 ?
C1 C2 H2 117.5 . . ?
C2 C2 C1 125.0(7) 5_666 . ?
C2 C2 H2 117.5 5_666 . ?
C4 C3 C9 119.3(5) . . ?
C8 C3 C4 119.9(5) . . ?
C8 C3 C9 120.8(5) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 C3 118.9(6) . . ?
C5 C4 H4 120.6 . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 121.0(6) . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C7 119.8(6) . . ?
C5 C6 C10 119.5(6) . . ?
C7 C6 C10 120.7(6) . . ?
C6 C7 H7 120.3 . . ?
C8 C7 C6 119.4(6) . . ?
C8 C7 H7 120.3 . . ?
C3 C8 C7 121.0(6) . . ?
C3 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
O3 C9 C3 118.6(5) . . ?
O4 C9 O3 123.0(5) . . ?
O4 C9 C3 118.4(5) . . ?
O5 C10 Eu1 36.6(3) . 3_646 ?
O5 C10 C6 117.0(5) . . ?
O6 C10 Eu1 92.4(4) . 3_646 ?
O6 C10 O5 124.0(6) . . ?
O6 C10 C6 119.1(6) . . ?
C6 C10 Eu1 142.6(4) . 3_646 ?

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
C2 H2 O3 0.93 2.41 3.209(7) 143.5 .

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
Eu1 Eu1 O1 Eu1 12.8(3) 8_765 . . 8_755 ?
Eu1 Eu1 O1 C1 -150.5(8) 8_755 . . . ?
Eu1 Eu1 O1 C1 -137.6(6) 8_765 . . . ?
Eu1 Eu1 O3 C9 147(2) 8_755 . . . ?
Eu1 Eu1 O3 C9 -21(3) 8_765 . . . ?
Eu1 O1 C1 Eu1 152.7(7) . . . 8_755 ?
Eu1 O1 C1 O2 154.3(4) . . . . ?
Eu1 O1 C1 O2 1.6(6) 8_755 . . . ?
Eu1 O1 C1 C2 -178.7(5) 8_755 . . . ?
Eu1 O1 C1 C2 -26.0(10) . . . . ?
Eu1 O2 C1 Eu1 113.7(5) 1_545 . . 8_755 ?
Eu1 O2 C1 O1 -1.5(6) 8_755 . . . ?
Eu1 O2 C1 O1 112.2(6) 1_545 . . . ?
Eu1 O2 C1 C2 178.8(6) 8_755 . . . ?
Eu1 O2 C1 C2 -67.5(8) 1_545 . . . ?
Eu1 O3 C9 O4 112(2) . . . . ?
Eu1 O3 C9 C3 -69(3) . . . . ?
Eu1 O4 C9 O3 21.7(10) 5_676 . . . ?
Eu1 O4 C9 C3 -157.4(5) 5_676 . . . ?
Eu1 O5 C10 O6 34.4(9) 3_646 . . . ?
Eu1 O5 C10 C6 -144.1(4) 3_646 . . . ?
Eu1 O6 C10 Eu1 53.8(6) 6_557 . . 3_646 ?
Eu1 O6 C10 O5 34.1(10) 6_557 . . . ?
Eu1 O6 C10 C6 -147.5(5) 6_557 . . . ?
Eu1 C1 C2 C2 171(4) 8_755 . . 5_666 ?
O1 Eu1 O1 Eu1 12.9(3) 8_765 . . 8_755 ?
O1 Eu1 O1 C1 -137.6(6) 8_765 . . . ?
O1 Eu1 O3 C9 157(2) . . . . ?
O1 Eu1 O3 C9 -12(3) 8_765 . . . ?
O1 C1 C2 C2 -176.9(10) . . . 5_666 ?
O2 Eu1 O1 Eu1 93.7(3) 1_565 . . 8_755 ?
O2 Eu1 O1 Eu1 26.75(14) 8_765 . . 8_755 ?
O2 Eu1 O1 C1 -56.8(8) 1_565 . . . ?
O2 Eu1 O1 C1 -123.7(7) 8_765 . . . ?
O2 Eu1 O3 C9 -49(2) 1_565 . . . ?
O2 Eu1 O3 C9 173(2) 8_765 . . . ?
O2 C1 C2 C2 2.8(14) . . . 5_666 ?
O3 Eu1 O1 Eu1 -164.18(19) . . . 8_755 ?
O3 Eu1 O1 C1 45.4(7) . . . . ?
O4 Eu1 O1 Eu1 107.21(19) 5_676 . . 8_755 ?
O4 Eu1 O1 C1 -43.2(7) 5_676 . . . ?
O4 Eu1 O3 C9 -125(2) 5_676 . . . ?
O5 Eu1 O1 Eu1 -104.7(2) 3_656 . . 8_755 ?
O5 Eu1 O1 C1 104.9(7) 3_656 . . . ?
O5 Eu1 O3 C9 15(2) 3_656 . . . ?
O6 Eu1 O1 Eu1 -58.02(18) 6_657 . . 8_755 ?
O6 Eu1 O1 C1 151.5(7) 6_657 . . . ?
O6 Eu1 O3 C9 86(2) 6_657 . . . ?
C1 Eu1 O1 Eu1 20.06(18) 8_765 . . 8_755 ?
C1 Eu1 O1 C1 -130.4(7) 8_765 . . . ?
C1 Eu1 O3 C9 179(2) 8_765 . . . ?
C3 C4 C5 C6 -2.8(11) . . . . ?
C4 C3 C8 C7 -0.2(10) . . . . ?
C4 C3 C9 O3 -13.9(9) . . . . ?
C4 C3 C9 O4 165.2(6) . . . . ?
C4 C5 C6 C7 0.4(10) . . . . ?
C4 C5 C6 C10 179.1(6) . . . . ?
C5 C6 C7 C8 2.1(10) . . . . ?
C5 C6 C10 Eu1 -48.1(9) . . . 3_646 ?
C5 C6 C10 O5 -13.0(9) . . . . ?
C5 C6 C10 O6 168.4(6) . . . . ?
C6 C7 C8 C3 -2.2(10) . . . . ?
C7 C6 C10 Eu1 130.6(6) . . . 3_646 ?
C7 C6 C10 O5 165.7(6) . . . . ?
C7 C6 C10 O6 -12.9(9) . . . . ?
C8 C3 C4 C5 2.7(10) . . . . ?
C8 C3 C9 O3 166.9(6) . . . . ?
C8 C3 C9 O4 -14.0(9) . . . . ?
C9 C3 C4 C5 -176.5(6) . . . . ?
C9 C3 C8 C7 179.0(6) . . . . ?
C10 Eu1 O1 Eu1 -77.8(2) 3_656 . . 8_755 ?
C10 Eu1 O1 C1 131.7(6) 3_656 . . . ?
C10 Eu1 O3 C9 20(2) 3_656 . . . ?
C10 C6 C7 C8 -176.6(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_4eu
_database_code_depnum_ccdc_archive 'CCDC 1863667'
_audit_update_record             
;
2018-08-24 deposited with the CCDC.
2018-09-26 downloaded from the CCDC.
;
_audit_creation_date             2018-03-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H16 Eu2 O16, 2(H2 O)'
_chemical_formula_sum            'C16 H20 Eu2 O18'
_chemical_formula_weight         804.24
_chemical_absolute_configuration unk
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Eu Eu -0.1578 3.6682 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.0081(3)
_cell_length_b                   12.4849(4)
_cell_length_c                   10.4062(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.2113(10)
_cell_angle_gamma                90
_cell_volume                     1139.36(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9965
_cell_measurement_temperature    296
_cell_measurement_theta_max      32.906
_cell_measurement_theta_min      3.157
_shelx_estimated_absorpt_T_max   0.665
_shelx_estimated_absorpt_T_min   0.375
_exptl_absorpt_coefficient_mu    5.544
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6282
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0697 before and 0.0498 after correction. The Ratio of minimum to maximum transmission is 0.8420. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.344
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             772
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            38748
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.586
_diffrn_reflns_theta_min         3.157
_diffrn_ambient_temperature      296.0
_diffrn_detector                 'Bruker PHOTON 100 area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'PHOTON area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'four-circle KAPPA diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_collimation    '0.5 mm'
_diffrn_radiation_monochromator  'graphiteDouble Bounce Multilayer Mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed x-ray tube'
_diffrn_source_target            Cu
_diffrn_source_type              'Incoatec I\mus'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.920
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                6662
_reflns_number_total             6962
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2016)'
_computing_data_collection       'APEX 3 (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.489
_refine_diff_density_min         -0.444
_refine_diff_density_rms         0.093
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.281(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     374
_refine_ls_number_reflns         6962
_refine_ls_number_restraints     19
_refine_ls_R_factor_all          0.0191
_refine_ls_R_factor_gt           0.0164
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0104P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0282
_refine_ls_wR_factor_ref         0.0286
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.719(8)
 0.281(8)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3. Restrained distances
 O14-H14A = O16-H16A
 0.84 with sigma of 0.01
 O14-H14B
 0.84 with sigma of 0.01
 H14A-H14B
 1.37 with sigma of 0.02
 O13-H13A
 0.84 with sigma of 0.01
 O17-H17A
 0.84 with sigma of 0.01
 O16-H16B
 0.84 with sigma of 0.01
 H16A-H16B
 1.355 with sigma of 0.02
 O17-H17B
 0.84 with sigma of 0.01
 H17A-H17B
 1.35 with sigma of 0.02
 O13-H13B
 0.84 with sigma of 0.01
 H13B-H13A
 1.365 with sigma of 0.02
 O15-H15A
 0.84 with sigma of 0.01
 O15-H15B
 0.84 with sigma of 0.01
 H15B-H15A
 1.37 with sigma of 0.02
 O18-H18A
 0.84 with sigma of 0.01
 O18-H18B
 0.84 with sigma of 0.01
 H18A-H18B
 1.39 with sigma of 0.02
4.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C10(H10), C11(H11), C14(H14), C15(H15)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 -0.38402(2) -0.58944(2) -0.67949(2) 0.01229(4) Uani 1 1 d . . . . .
Eu2 Eu -0.07365(2) -0.50574(2) -0.88290(2) 0.01189(4) Uani 1 1 d . . . . .
O1 O -0.4395(3) -0.6197(2) -0.4622(3) 0.0349(8) Uani 1 1 d . . . . .
O2 O -0.5998(3) -0.5143(3) -0.5895(2) 0.0286(6) Uani 1 1 d . . . . .
O3 O -0.8578(3) -0.5705(2) 0.0296(2) 0.0279(7) Uani 1 1 d . . . . .
O4 O -1.0376(4) -0.4893(3) -0.1114(3) 0.0461(9) Uani 1 1 d . . . . .
O5 O -0.1348(3) -0.6552(2) -0.5793(3) 0.0234(6) Uani 1 1 d . . . . .
O6 O 0.0235(3) -0.6278(2) -0.7136(3) 0.0237(6) Uani 1 1 d . . . . .
O7 O 0.1842(3) -0.94429(19) -0.2879(2) 0.0194(5) Uani 1 1 d . . . . .
O8 O 0.2801(4) -0.9345(2) -0.4612(3) 0.0324(7) Uani 1 1 d . . . . .
O9 O -0.4872(3) -0.4742(2) -0.8579(2) 0.0217(6) Uani 1 1 d . . . . .
O10 O -0.3253(3) -0.4520(2) -0.9905(3) 0.0244(6) Uani 1 1 d . . . . .
O11 O -0.8561(4) -0.1765(3) -1.0042(3) 0.0411(8) Uani 1 1 d . . . . .
O12 O -0.7092(3) -0.1590(2) -1.1423(3) 0.0211(6) Uani 1 1 d . . . . .
O13 O -0.3910(4) -0.7846(3) -0.6392(4) 0.0457(9) Uani 1 1 d D . . . .
H13A H -0.467(4) -0.824(3) -0.656(4) 0.039(14) Uiso 1 1 d D . . . .
H13B H -0.354(8) -0.787(7) -0.558(2) 0.16(4) Uiso 1 1 d D . . . .
O14 O -0.6256(3) -0.6691(3) -0.8014(3) 0.0292(6) Uani 1 1 d D . . . .
H14A H -0.688(5) -0.621(4) -0.835(6) 0.10(3) Uiso 1 1 d D . . . .
H14B H -0.671(6) -0.718(3) -0.771(6) 0.08(2) Uiso 1 1 d D . . . .
O15 O -0.0748(4) -0.3110(3) -0.9319(4) 0.0404(8) Uani 1 1 d D . . . .
H15A H -0.005(5) -0.288(6) -0.966(6) 0.12(3) Uiso 1 1 d D . . . .
H15B H -0.159(3) -0.287(5) -0.971(5) 0.08(2) Uiso 1 1 d D . . . .
O16 O 0.1489(3) -0.4208(2) -0.7485(3) 0.0273(6) Uani 1 1 d D . . . .
H16A H 0.217(3) -0.456(2) -0.702(4) 0.026(12) Uiso 1 1 d D . . . .
H16B H 0.169(5) -0.3559(13) -0.745(5) 0.053(16) Uiso 1 1 d D . . . .
C1 C -0.6530(4) -0.5605(3) -0.3812(4) 0.0195(8) Uani 1 1 d . . . . .
C2 C -0.5977(5) -0.6054(4) -0.2574(4) 0.0293(10) Uani 1 1 d . . . . .
H2 H -0.503848 -0.640139 -0.238693 0.035 Uiso 1 1 calc R . . . .
C3 C -0.6817(4) -0.5988(4) -0.1617(4) 0.0288(9) Uani 1 1 d . . . . .
H3 H -0.644075 -0.628682 -0.078753 0.035 Uiso 1 1 calc R . . . .
C4 C -0.8222(4) -0.5475(3) -0.1895(4) 0.0201(8) Uani 1 1 d . . . . .
C5 C -0.8791(4) -0.5068(4) -0.3132(4) 0.0251(8) Uani 1 1 d . . . . .
H5 H -0.975411 -0.475708 -0.333266 0.030 Uiso 1 1 calc R . . . .
C6 C -0.7941(4) -0.5115(4) -0.4091(3) 0.0227(7) Uani 1 1 d . . . . .
H6 H -0.832376 -0.481724 -0.491920 0.027 Uiso 1 1 calc R . . . .
C7 C -0.5598(4) -0.5642(3) -0.4830(4) 0.0189(8) Uani 1 1 d . . . . .
C8 C -0.9110(4) -0.5346(3) -0.0851(4) 0.0200(9) Uani 1 1 d . . . . .
C9 C -0.0159(4) -0.6735(3) -0.6195(3) 0.0182(7) Uani 1 1 d . . . . .
C10 C 0.0896(4) -0.7601(3) -0.5555(4) 0.0262(8) Uani 1 1 d . . . . .
H10 H 0.165553 -0.780692 -0.597750 0.031 Uiso 1 1 calc R . . . .
C11 C 0.0853(4) -0.8100(3) -0.4456(4) 0.0218(8) Uani 1 1 d . . . . .
H11 H 0.015330 -0.788472 -0.397465 0.026 Uiso 1 1 calc R . . . .
C12 C 0.1904(4) -0.9003(3) -0.3964(4) 0.0183(7) Uani 1 1 d . . . . .
C13 C -0.4450(4) -0.4301(3) -0.9512(3) 0.0173(7) Uani 1 1 d . . . . .
C14 C -0.5388(4) -0.3409(3) -1.0220(4) 0.0225(8) Uani 1 1 d . . . . .
H14 H -0.509356 -0.309862 -1.093503 0.027 Uiso 1 1 calc R . . . .
C15 C -0.6604(4) -0.3040(3) -0.9887(4) 0.0247(8) Uani 1 1 d . . . . .
H15 H -0.695707 -0.339530 -0.923046 0.030 Uiso 1 1 calc R . . . .
C16 C -0.7449(4) -0.2085(3) -1.0503(4) 0.0207(8) Uani 1 1 d . . . . .
O17 O -0.6665(4) -0.8867(3) -0.7178(4) 0.0447(8) Uani 1 1 d D . . . .
H17A H -0.699(7) -0.923(4) -0.663(4) 0.08(2) Uiso 1 1 d D . . . .
H17B H -0.693(7) -0.918(4) -0.790(3) 0.07(2) Uiso 1 1 d D . . . .
O18 O 0.1947(5) -0.2095(3) -0.7179(4) 0.0587(11) Uani 1 1 d D . . . .
H18A H 0.200(7) -0.193(5) -0.794(2) 0.09(3) Uiso 1 1 d D . . . .
H18B H 0.256(5) -0.177(4) -0.660(3) 0.047(15) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Eu1 O1 2.454(3) . ?
Eu1 O2 2.523(2) . ?
Eu1 O5 2.394(3) . ?
Eu1 O7 2.630(3) 2_554 ?
Eu1 O8 2.477(3) 2_554 ?
Eu1 O9 2.365(2) . ?
Eu1 O12 2.369(2) 2_443 ?
Eu1 O13 2.475(3) . ?
Eu1 H13B 2.76(7) . ?
Eu1 O14 2.464(3) . ?
Eu2 O3 2.465(3) 1_654 ?
Eu2 O4 2.481(3) 1_654 ?
Eu2 O6 2.343(2) . ?
Eu2 O7 2.356(2) 2_554 ?
Eu2 O10 2.384(3) . ?
Eu2 O11 2.447(3) 2_443 ?
Eu2 O12 2.791(3) 2_443 ?
Eu2 O15 2.484(3) . ?
Eu2 O16 2.413(3) . ?
O1 C7 1.262(4) . ?
O2 C7 1.251(5) . ?
O3 C8 1.262(5) . ?
O4 C8 1.246(5) . ?
O5 C9 1.256(4) . ?
O6 C9 1.253(4) . ?
O7 C12 1.268(4) . ?
O8 C12 1.241(4) . ?
O9 C13 1.247(4) . ?
O10 C13 1.267(4) . ?
O11 C16 1.269(5) . ?
O12 C16 1.242(4) . ?
O13 H13A 0.831(14) . ?
O13 H13B 0.837(14) . ?
O14 H14A 0.841(14) . ?
O14 H14B 0.837(14) . ?
O15 H15A 0.839(14) . ?
O15 H15B 0.830(14) . ?
O16 H16A 0.821(14) . ?
O16 H16B 0.829(14) . ?
C1 C2 1.389(5) . ?
C1 C6 1.381(5) . ?
C1 C7 1.495(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.384(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.388(6) . ?
C4 C5 1.370(5) . ?
C4 C8 1.498(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.390(5) . ?
C6 H6 0.9300 . ?
C9 C10 1.492(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.311(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.485(5) . ?
C13 C14 1.488(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.306(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.479(5) . ?
O17 H17A 0.835(14) . ?
O17 H17B 0.834(14) . ?
O18 H18A 0.832(14) . ?
O18 H18B 0.830(14) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Eu1 O2 51.60(9) . . ?
O1 Eu1 O7 120.95(10) . 2_554 ?
O1 Eu1 O8 72.81(10) . 2_554 ?
O1 Eu1 O13 70.98(12) . . ?
O1 Eu1 H13B 57.1(14) . . ?
O1 Eu1 O14 94.04(11) . . ?
O2 Eu1 O7 113.55(10) . 2_554 ?
O2 Eu1 H13B 99.4(17) . . ?
O5 Eu1 O1 85.07(9) . . ?
O5 Eu1 O2 133.72(8) . . ?
O5 Eu1 O7 72.01(9) . 2_554 ?
O5 Eu1 O8 79.63(11) . 2_554 ?
O5 Eu1 O13 69.29(11) . . ?
O5 Eu1 H13B 60.7(13) . . ?
O5 Eu1 O14 135.72(11) . . ?
O7 Eu1 H13B 132.7(13) 2_554 . ?
O8 Eu1 O2 73.11(10) 2_554 . ?
O8 Eu1 O7 50.27(8) 2_554 2_554 ?
O8 Eu1 H13B 116.3(8) 2_554 . ?
O9 Eu1 O1 133.70(9) . . ?
O9 Eu1 O2 82.38(9) . . ?
O9 Eu1 O5 135.37(9) . . ?
O9 Eu1 O7 68.73(8) . 2_554 ?
O9 Eu1 O8 90.95(10) . 2_554 ?
O9 Eu1 O12 75.79(9) . 2_443 ?
O9 Eu1 O13 135.34(11) . . ?
O9 Eu1 H13B 152.2(7) . . ?
O9 Eu1 O14 72.48(10) . . ?
O12 Eu1 O1 148.02(9) 2_443 . ?
O12 Eu1 O2 150.22(8) 2_443 . ?
O12 Eu1 O5 75.54(9) 2_443 . ?
O12 Eu1 O7 77.07(8) 2_443 2_554 ?
O12 Eu1 O8 126.54(9) 2_443 2_554 ?
O12 Eu1 O13 78.39(12) 2_443 . ?
O12 Eu1 H13B 91.0(15) 2_443 . ?
O12 Eu1 O14 83.02(10) 2_443 . ?
O13 Eu1 O2 104.57(12) . . ?
O13 Eu1 O7 138.12(11) . 2_554 ?
O13 Eu1 O8 133.57(12) . 2_554 ?
O13 Eu1 H13B 17.4(8) . . ?
O14 Eu1 O2 71.12(10) . . ?
O14 Eu1 O7 139.60(9) . 2_554 ?
O14 Eu1 O8 142.14(11) . 2_554 ?
O14 Eu1 O13 68.69(12) . . ?
O14 Eu1 H13B 81.8(10) . . ?
O3 Eu2 O4 52.10(9) 1_654 1_654 ?
O3 Eu2 O12 116.03(9) 1_654 2_443 ?
O3 Eu2 O15 102.23(11) 1_654 . ?
O4 Eu2 O12 113.27(11) 1_654 2_443 ?
O4 Eu2 O15 73.58(13) 1_654 . ?
O6 Eu2 O3 82.75(9) . 1_654 ?
O6 Eu2 O4 131.80(10) . 1_654 ?
O6 Eu2 O7 78.12(9) . 2_554 ?
O6 Eu2 O10 133.49(9) . . ?
O6 Eu2 O11 78.78(11) . 2_443 ?
O6 Eu2 O12 68.46(9) . 2_443 ?
O6 Eu2 O15 140.75(11) . . ?
O6 Eu2 O16 74.43(10) . . ?
O7 Eu2 O3 153.01(9) 2_554 1_654 ?
O7 Eu2 O4 150.09(9) 2_554 1_654 ?
O7 Eu2 O10 75.04(9) 2_554 . ?
O7 Eu2 O11 122.58(9) 2_554 2_443 ?
O7 Eu2 O12 74.11(8) 2_554 2_443 ?
O7 Eu2 O15 81.58(11) 2_554 . ?
O7 Eu2 O16 81.83(10) 2_554 . ?
O10 Eu2 O3 131.66(9) . 1_654 ?
O10 Eu2 O4 81.11(9) . 1_654 ?
O10 Eu2 O11 84.62(11) . 2_443 ?
O10 Eu2 O12 68.02(9) . 2_443 ?
O10 Eu2 O15 70.67(10) . . ?
O10 Eu2 O16 136.34(10) . . ?
O11 Eu2 O3 71.10(9) 2_443 1_654 ?
O11 Eu2 O4 71.84(12) 2_443 1_654 ?
O11 Eu2 O12 48.53(8) 2_443 2_443 ?
O11 Eu2 O15 140.00(13) 2_443 . ?
O15 Eu2 O12 136.08(10) . 2_443 ?
O16 Eu2 O3 74.77(10) . 1_654 ?
O16 Eu2 O4 104.23(12) . 1_654 ?
O16 Eu2 O11 138.68(11) . 2_443 ?
O16 Eu2 O12 138.96(9) . 2_443 ?
O16 Eu2 O15 69.66(11) . . ?
C7 O1 Eu1 96.0(2) . . ?
C7 O2 Eu1 93.1(2) . . ?
C8 O3 Eu2 94.1(2) . 1_456 ?
C8 O4 Eu2 93.8(2) . 1_456 ?
C9 O5 Eu1 134.7(2) . . ?
C9 O6 Eu2 139.5(2) . . ?
Eu2 O7 Eu1 107.02(9) 2_544 2_544 ?
C12 O7 Eu1 90.7(2) . 2_544 ?
C12 O7 Eu2 157.7(2) . 2_544 ?
C12 O8 Eu1 98.8(2) . 2_544 ?
C13 O9 Eu1 138.1(2) . . ?
C13 O10 Eu2 134.2(2) . . ?
C16 O11 Eu2 103.4(2) . 2_453 ?
Eu1 O12 Eu2 101.75(8) 2_453 2_453 ?
C16 O12 Eu1 170.6(3) . 2_453 ?
C16 O12 Eu2 87.6(2) . 2_453 ?
Eu1 O13 H13A 127(3) . . ?
Eu1 O13 H13B 101(6) . . ?
H13A O13 H13B 108(3) . . ?
Eu1 O14 H14A 111(4) . . ?
Eu1 O14 H14B 123(4) . . ?
H14A O14 H14B 109(3) . . ?
Eu2 O15 H15A 117(5) . . ?
Eu2 O15 H15B 115(4) . . ?
H15A O15 H15B 111(3) . . ?
Eu2 O16 H16A 121(3) . . ?
Eu2 O16 H16B 127(3) . . ?
H16A O16 H16B 112(3) . . ?
C2 C1 C7 120.3(3) . . ?
C6 C1 C2 119.4(3) . . ?
C6 C1 C7 120.3(3) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.3(4) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 120.0(4) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C8 120.7(3) . . ?
C5 C4 C3 119.6(3) . . ?
C5 C4 C8 119.6(3) . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.6(3) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 120.0(3) . . ?
C1 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
O1 C7 C1 119.7(3) . . ?
O2 C7 O1 119.2(3) . . ?
O2 C7 C1 121.2(3) . . ?
O3 C8 Eu2 59.67(18) . 1_456 ?
O3 C8 C4 119.8(3) . . ?
O4 C8 Eu2 60.35(19) . 1_456 ?
O4 C8 O3 120.0(3) . . ?
O4 C8 C4 120.2(3) . . ?
C4 C8 Eu2 178.4(3) . 1_456 ?
O5 C9 C10 119.2(3) . . ?
O6 C9 O5 126.4(3) . . ?
O6 C9 C10 114.4(3) . . ?
C9 C10 H10 116.9 . . ?
C11 C10 C9 126.2(4) . . ?
C11 C10 H10 116.9 . . ?
C10 C11 H11 119.4 . . ?
C10 C11 C12 121.2(4) . . ?
C12 C11 H11 119.4 . . ?
O7 C12 Eu1 63.65(18) . 2_544 ?
O7 C12 C11 118.8(3) . . ?
O8 C12 Eu1 56.51(19) . 2_544 ?
O8 C12 O7 120.1(3) . . ?
O8 C12 C11 121.1(3) . . ?
C11 C12 Eu1 174.9(3) . 2_544 ?
O9 C13 O10 126.1(3) . . ?
O9 C13 C14 118.4(3) . . ?
O10 C13 C14 115.5(3) . . ?
C13 C14 H14 118.3 . . ?
C15 C14 C13 123.3(3) . . ?
C15 C14 H14 118.3 . . ?
C14 C15 H15 118.3 . . ?
C14 C15 C16 123.4(3) . . ?
C16 C15 H15 118.3 . . ?
O11 C16 Eu2 52.32(18) . 2_453 ?
O11 C16 C15 117.5(3) . . ?
O12 C16 Eu2 68.1(2) . 2_453 ?
O12 C16 O11 120.1(3) . . ?
O12 C16 C15 122.4(3) . . ?
C15 C16 Eu2 167.8(3) . 2_453 ?
H17A O17 H17B 107(3) . . ?
H18A O18 H18B 114(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
O13 H13A O17 0.831(14) 1.928(17) 2.744(5) 167(5) .
O14 H14A O3 0.841(14) 1.93(4) 2.702(4) 151(7) 1_554
O14 H14B O17 0.837(14) 2.18(3) 2.902(5) 145(5) .
O15 H15A O11 0.839(14) 2.03(4) 2.818(5) 156(8) 1_655
O15 H15B O3 0.830(14) 2.78(6) 3.184(4) 112(5) 2_454
O16 H16A O2 0.821(14) 1.932(17) 2.741(4) 169(4) 1_655
O16 H16B O18 0.829(14) 1.855(17) 2.677(5) 171(6) .
O17 H17A O8 0.835(14) 2.15(3) 2.882(5) 146(5) 1_455
O17 H17B O4 0.834(14) 2.56(5) 3.121(5) 125(5) 2_344
O17 H17B O10 0.834(14) 2.36(3) 3.128(5) 152(5) 2_443
O18 H18A O11 0.832(14) 2.14(2) 2.938(5) 162(5) 1_655
O18 H18B O1 0.830(14) 1.970(19) 2.783(5) 166(5) 2_554

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Eu1 O1 C7 O2 -3.7(4) . . . . ?
Eu1 O1 C7 C1 175.4(3) . . . . ?
Eu1 O2 C7 O1 3.6(4) . . . . ?
Eu1 O2 C7 C1 -175.5(3) . . . . ?
Eu1 O5 C9 O6 27.4(6) . . . . ?
Eu1 O5 C9 C10 -150.1(3) . . . . ?
Eu1 O7 C12 O8 -3.3(4) 2_544 . . . ?
Eu1 O7 C12 C11 174.9(3) 2_544 . . . ?
Eu1 O8 C12 O7 3.5(4) 2_544 . . . ?
Eu1 O8 C12 C11 -174.6(3) 2_544 . . . ?
Eu1 O9 C13 O10 13.0(6) . . . . ?
Eu1 O9 C13 C14 -164.8(3) . . . . ?
Eu2 O3 C8 O4 -2.3(4) 1_456 . . . ?
Eu2 O3 C8 C4 178.2(3) 1_456 . . . ?
Eu2 O4 C8 O3 2.2(4) 1_456 . . . ?
Eu2 O4 C8 C4 -178.2(3) 1_456 . . . ?
Eu2 O6 C9 O5 -7.3(6) . . . . ?
Eu2 O6 C9 C10 170.3(3) . . . . ?
Eu2 O7 C12 Eu1 -143.3(6) 2_544 . . 2_544 ?
Eu2 O7 C12 O8 -146.6(5) 2_544 . . . ?
Eu2 O7 C12 C11 31.6(8) 2_544 . . . ?
Eu2 O10 C13 O9 -35.1(6) . . . . ?
Eu2 O10 C13 C14 142.7(3) . . . . ?
Eu2 O11 C16 O12 -7.1(4) 2_453 . . . ?
Eu2 O11 C16 C15 171.9(3) 2_453 . . . ?
Eu2 O12 C16 O11 6.0(4) 2_453 . . . ?
Eu2 O12 C16 C15 -172.9(4) 2_453 . . . ?
O5 C9 C10 C11 -11.8(6) . . . . ?
O6 C9 C10 C11 170.4(4) . . . . ?
O9 C13 C14 C15 2.3(6) . . . . ?
O10 C13 C14 C15 -175.7(4) . . . . ?
C1 C2 C3 C4 0.3(7) . . . . ?
C2 C1 C6 C5 0.5(6) . . . . ?
C2 C1 C7 O1 8.8(5) . . . . ?
C2 C1 C7 O2 -172.1(4) . . . . ?
C2 C3 C4 C5 2.1(7) . . . . ?
C2 C3 C4 C8 -176.8(4) . . . . ?
C3 C4 C5 C6 -3.3(7) . . . . ?
C3 C4 C8 O3 0.1(6) . . . . ?
C3 C4 C8 O4 -179.4(4) . . . . ?
C4 C5 C6 C1 2.0(7) . . . . ?
C5 C4 C8 O3 -178.8(4) . . . . ?
C5 C4 C8 O4 1.6(6) . . . . ?
C6 C1 C2 C3 -1.6(6) . . . . ?
C6 C1 C7 O1 -171.8(4) . . . . ?
C6 C1 C7 O2 7.3(5) . . . . ?
C7 C1 C2 C3 177.8(4) . . . . ?
C7 C1 C6 C5 -178.9(4) . . . . ?
C8 C4 C5 C6 175.7(4) . . . . ?
C9 C10 C11 C12 175.8(3) . . . . ?
C10 C11 C12 O7 178.3(4) . . . . ?
C10 C11 C12 O8 -3.5(6) . . . . ?
C13 C14 C15 C16 173.7(4) . . . . ?
C14 C15 C16 Eu2 -144.0(11) . . . 2_453 ?
C14 C15 C16 O11 -175.9(4) . . . . ?
C14 C15 C16 O12 3.0(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.719(8)
2 0.281(8)

####################################################################### 
# 
# 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_5tb
_database_code_depnum_ccdc_archive 'CCDC 1863668'
_audit_update_record             
;
2018-08-24 deposited with the CCDC.
2018-09-26 downloaded from the CCDC.
;
_audit_creation_date             2018-03-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H16 O16 Tb2, 2(H2 O)'
_chemical_formula_sum            'C16 H20 O18 Tb2'
_chemical_formula_weight         818.16
_chemical_absolute_configuration unk
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.9635(3)
_cell_length_b                   12.4252(4)
_cell_length_c                   10.3811(4)
_cell_angle_alpha                90
_cell_angle_beta                 103.1226(11)
_cell_angle_gamma                90
_cell_volume                     1125.99(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9953
_cell_measurement_temperature    296
_cell_measurement_theta_max      28.197
_cell_measurement_theta_min      3.171
_shelx_estimated_absorpt_T_max   0.431
_shelx_estimated_absorpt_T_min   0.365
_exptl_absorpt_coefficient_mu    6.320
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6583
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0806 before and 0.0695 after correction. The Ratio of minimum to maximum transmission is 0.8828. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.413
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             780
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0684
_diffrn_reflns_av_unetI/netI     0.0474
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            38307
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.380
_diffrn_reflns_theta_min         2.852
_diffrn_ambient_temperature      296.0
_diffrn_detector                 'Bruker PHOTON 100 area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'PHOTON area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'four-circle KAPPA diffractometer'
_diffrn_measurement_device_type  'BRUKER D8 QUEST CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_collimation    '0.5 mm'
_diffrn_radiation_monochromator  'graphiteDouble Bounce Multilayer Mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed x-ray tube'
_diffrn_source_target            Cu
_diffrn_source_type              'Incoatec I\mus'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.915
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                5030
_reflns_number_total             5578
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2016)'
_computing_data_collection       'APEX 3 (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.009
_refine_diff_density_min         -1.157
_refine_diff_density_rms         0.168
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.451(17)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     374
_refine_ls_number_reflns         5578
_refine_ls_number_restraints     19
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0281
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0242P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0484
_refine_ls_wR_factor_ref         0.0508
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.549(17)
 0.451(17)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3. Restrained distances
 O14-H14A = O16-H16A
 0.84 with sigma of 0.01
 O14-H14B
 0.84 with sigma of 0.01
 H14A-H14B
 1.37 with sigma of 0.02
 O17-H17A
 0.84 with sigma of 0.01
 O16-H16B
 0.84 with sigma of 0.01
 H16A-H16B
 1.355 with sigma of 0.02
 O17-H17B
 0.84 with sigma of 0.01
 H17A-H17B
 1.365 with sigma of 0.02
 O13-H13A
 0.84 with sigma of 0.01
 O15-H15A
 0.84 with sigma of 0.01
 O15-H15B
 0.84 with sigma of 0.01
 H15B-H15A
 1.37 with sigma of 0.02
 O18-H18A
 0.84 with sigma of 0.01
 O18-H18B
 0.84 with sigma of 0.01
 H18A-H18B
 1.37 with sigma of 0.02
 O13-H13B
 0.84 with sigma of 0.01
 H13A-H13B
 1.355 with sigma of 0.02
4.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C10(H10), C11(H11), C14(H14), C15(H15)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 -0.38321(4) -0.58958(2) -0.67921(3) 0.01290(9) Uani 1 1 d . . . . .
Tb2 Tb -0.07276(4) -0.50556(3) -0.88233(3) 0.01254(9) Uani 1 1 d . . . . .
O1 O -0.4370(7) -0.6195(5) -0.4628(6) 0.0338(17) Uani 1 1 d . . . . .
O2 O -0.5984(6) -0.5140(6) -0.5903(5) 0.0298(13) Uani 1 1 d . . . . .
O3 O -0.8570(6) -0.5710(6) 0.0315(5) 0.0295(15) Uani 1 1 d . . . . .
O4 O -1.0382(8) -0.4880(7) -0.1092(6) 0.046(2) Uani 1 1 d . . . . .
O5 O -0.1345(6) -0.6534(5) -0.5789(6) 0.0222(13) Uani 1 1 d . . . . .
O6 O 0.0233(6) -0.6277(5) -0.7153(6) 0.0232(13) Uani 1 1 d . . . . .
O7 O 0.1821(6) -0.9450(5) -0.2867(5) 0.0204(12) Uani 1 1 d . . . . .
O8 O 0.2806(7) -0.9341(5) -0.4591(6) 0.0309(16) Uani 1 1 d . . . . .
O9 O -0.4862(6) -0.4748(4) -0.8558(5) 0.0226(14) Uani 1 1 d . . . . .
O10 O -0.3233(6) -0.4535(5) -0.9889(6) 0.0229(14) Uani 1 1 d . . . . .
O11 O -0.8563(8) -0.1742(5) -1.0064(7) 0.0363(17) Uani 1 1 d . . . . .
O12 O -0.7083(6) -0.1599(5) -1.1455(5) 0.0217(13) Uani 1 1 d . . . . .
O13 O -0.3908(9) -0.7825(6) -0.6381(9) 0.049(2) Uani 1 1 d D . . . .
H13A H -0.463(6) -0.826(5) -0.660(8) 0.02(2) Uiso 1 1 d D . . . .
O14 O -0.6230(7) -0.6696(6) -0.7981(7) 0.0322(15) Uani 1 1 d D . . . .
H14A H -0.693(7) -0.632(5) -0.845(7) 0.02(2) Uiso 1 1 d D . . . .
H14B H -0.662(10) -0.713(11) -0.754(15) 0.18(10) Uiso 1 1 d D . . . .
O15 O -0.0761(8) -0.3115(5) -0.9318(8) 0.0388(17) Uani 1 1 d D . . . .
H15A H 0.000(8) -0.296(10) -0.963(11) 0.07(4) Uiso 1 1 d D . . . .
H15B H -0.141(17) -0.262(12) -0.95(3) 0.30(16) Uiso 1 1 d D . . . .
O16 O 0.1482(7) -0.4203(5) -0.7498(6) 0.0262(14) Uani 1 1 d D . . . .
H16A H 0.204(9) -0.463(5) -0.699(7) 0.03(3) Uiso 1 1 d D . . . .
H16B H 0.161(16) -0.358(3) -0.718(11) 0.11(6) Uiso 1 1 d D . . . .
O17 O -0.6660(9) -0.8871(6) -0.7177(8) 0.0439(18) Uani 1 1 d D . . . .
H17A H -0.703(11) -0.910(8) -0.656(6) 0.05(3) Uiso 1 1 d D . . . .
H17B H -0.693(11) -0.927(6) -0.784(5) 0.03(3) Uiso 1 1 d D . . . .
O18 O 0.1944(10) -0.2086(6) -0.7194(8) 0.054(2) Uani 1 1 d D . . . .
H18A H 0.182(15) -0.177(12) -0.792(7) 0.12(7) Uiso 1 1 d D . . . .
H18B H 0.274(9) -0.185(10) -0.669(9) 0.08(5) Uiso 1 1 d D . . . .
C1 C -0.6517(10) -0.5605(7) -0.3823(8) 0.022(2) Uani 1 1 d . . . . .
C2 C -0.5971(10) -0.6065(8) -0.2577(9) 0.031(2) Uani 1 1 d . . . . .
H2 H -0.502445 -0.640884 -0.238906 0.037 Uiso 1 1 calc R . . . .
C3 C -0.6816(10) -0.6017(9) -0.1620(8) 0.029(2) Uani 1 1 d . . . . .
H3 H -0.645078 -0.633873 -0.080055 0.035 Uiso 1 1 calc R . . . .
C4 C -0.8215(9) -0.5485(7) -0.1889(8) 0.0187(18) Uani 1 1 d . . . . .
C5 C -0.8788(10) -0.5061(10) -0.3122(8) 0.0273(19) Uani 1 1 d . . . . .
H5 H -0.974462 -0.473150 -0.331147 0.033 Uiso 1 1 calc R . . . .
C6 C -0.7951(9) -0.5121(9) -0.4082(8) 0.0259(18) Uani 1 1 d . . . . .
H6 H -0.835268 -0.483328 -0.491570 0.031 Uiso 1 1 calc R . . . .
C7 C -0.5583(10) -0.5654(7) -0.4844(9) 0.024(2) Uani 1 1 d . . . . .
C8 C -0.9106(10) -0.5357(7) -0.0833(9) 0.021(2) Uani 1 1 d . . . . .
C9 C -0.0154(8) -0.6722(7) -0.6195(8) 0.0185(17) Uani 1 1 d . . . . .
C10 C 0.0905(10) -0.7591(7) -0.5551(8) 0.0255(19) Uani 1 1 d . . . . .
H10 H 0.167577 -0.779550 -0.596771 0.031 Uiso 1 1 calc R . . . .
C11 C 0.0850(10) -0.8095(7) -0.4448(8) 0.0231(19) Uani 1 1 d . . . . .
H11 H 0.014456 -0.787621 -0.396792 0.028 Uiso 1 1 calc R . . . .
C12 C 0.1892(9) -0.9004(7) -0.3958(8) 0.0188(17) Uani 1 1 d . . . . .
C13 C -0.4437(9) -0.4311(6) -0.9507(8) 0.0188(17) Uani 1 1 d . . . . .
C14 C -0.5379(9) -0.3433(8) -1.0219(9) 0.0240(19) Uani 1 1 d . . . . .
H14 H -0.509668 -0.314286 -1.095441 0.029 Uiso 1 1 calc R . . . .
C15 C -0.6587(10) -0.3035(7) -0.9885(8) 0.0242(19) Uani 1 1 d . . . . .
H15 H -0.692725 -0.337222 -0.920472 0.029 Uiso 1 1 calc R . . . .
C16 C -0.7453(9) -0.2083(7) -1.0515(8) 0.0203(18) Uani 1 1 d . . . . .
H13B H -0.308(5) -0.815(7) -0.628(16) 0.12(7) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Tb1 O1 2.431(6) . ?
Tb1 O2 2.502(5) . ?
Tb1 O5 2.373(6) . ?
Tb1 O7 2.626(6) 2_554 ?
Tb1 O8 2.458(6) 2_554 ?
Tb1 O9 2.341(5) . ?
Tb1 O12 2.329(5) 2_443 ?
Tb1 O13 2.438(7) . ?
Tb1 O14 2.434(6) . ?
Tb2 O3 2.447(5) 1_654 ?
Tb2 O4 2.454(6) 1_654 ?
Tb2 O6 2.318(5) . ?
Tb2 O7 2.321(5) 2_554 ?
Tb2 O10 2.357(6) . ?
Tb2 O11 2.408(6) 2_443 ?
Tb2 O12 2.806(6) 2_443 ?
Tb2 O15 2.464(7) . ?
Tb2 O16 2.388(6) . ?
Tb2 C8 2.825(8) 1_654 ?
O1 C7 1.254(10) . ?
O2 C7 1.252(10) . ?
O3 C8 1.258(10) . ?
O4 C8 1.261(10) . ?
O5 C9 1.255(9) . ?
O6 C9 1.254(10) . ?
O7 C12 1.275(9) . ?
O8 C12 1.234(10) . ?
O9 C13 1.257(9) . ?
O10 C13 1.262(10) . ?
O11 C16 1.265(10) . ?
O12 C16 1.253(9) . ?
O13 H13A 0.833(15) . ?
O13 H13B 0.835(15) . ?
O14 H14A 0.840(15) . ?
O14 H14B 0.840(15) . ?
O15 H15A 0.839(15) . ?
O15 H15B 0.839(15) . ?
O16 H16A 0.834(15) . ?
O16 H16B 0.837(15) . ?
O17 H17A 0.839(15) . ?
O17 H17B 0.837(15) . ?
O18 H18A 0.838(15) . ?
O18 H18B 0.840(15) . ?
C1 C2 1.397(12) . ?
C1 C6 1.389(12) . ?
C1 C7 1.494(11) . ?
C2 H2 0.9300 . ?
C2 C3 1.380(12) . ?
C3 H3 0.9300 . ?
C3 C4 1.388(12) . ?
C4 C5 1.372(12) . ?
C4 C8 1.504(11) . ?
C5 H5 0.9300 . ?
C5 C6 1.379(11) . ?
C6 H6 0.9300 . ?
C9 C10 1.492(11) . ?
C10 H10 0.9300 . ?
C10 C11 1.316(12) . ?
C11 H11 0.9300 . ?
C11 C12 1.480(11) . ?
C13 C14 1.472(11) . ?
C14 H14 0.9300 . ?
C14 C15 1.307(12) . ?
C15 H15 0.9300 . ?
C15 C16 1.483(11) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Tb1 O2 52.1(2) . . ?
O1 Tb1 O7 121.0(2) . 2_554 ?
O1 Tb1 O8 72.9(2) . 2_554 ?
O1 Tb1 O13 70.7(3) . . ?
O1 Tb1 O14 93.9(2) . . ?
O2 Tb1 O7 113.8(2) . 2_554 ?
O5 Tb1 O1 84.7(2) . . ?
O5 Tb1 O2 133.61(19) . . ?
O5 Tb1 O7 71.48(19) . 2_554 ?
O5 Tb1 O8 79.4(2) . 2_554 ?
O5 Tb1 O13 69.8(2) . . ?
O5 Tb1 O14 136.0(2) . . ?
O8 Tb1 O2 73.0(2) 2_554 . ?
O8 Tb1 O7 50.48(19) 2_554 2_554 ?
O9 Tb1 O1 133.7(2) . . ?
O9 Tb1 O2 82.0(2) . . ?
O9 Tb1 O5 135.37(19) . . ?
O9 Tb1 O7 68.79(19) . 2_554 ?
O9 Tb1 O8 90.4(2) . 2_554 ?
O9 Tb1 O13 135.6(2) . . ?
O9 Tb1 O14 72.9(2) . . ?
O12 Tb1 O1 147.5(2) 2_443 . ?
O12 Tb1 O2 150.04(19) 2_443 . ?
O12 Tb1 O5 75.8(2) 2_443 . ?
O12 Tb1 O7 77.12(18) 2_443 2_554 ?
O12 Tb1 O8 126.9(2) 2_443 2_554 ?
O12 Tb1 O9 76.3(2) 2_443 . ?
O12 Tb1 O13 78.3(3) 2_443 . ?
O12 Tb1 O14 83.0(2) 2_443 . ?
O13 Tb1 O2 104.5(3) . . ?
O13 Tb1 O7 138.0(2) . 2_554 ?
O13 Tb1 O8 133.8(3) . 2_554 ?
O14 Tb1 O2 71.0(2) . . ?
O14 Tb1 O7 139.9(2) . 2_554 ?
O14 Tb1 O8 141.9(2) . 2_554 ?
O14 Tb1 O13 68.3(3) . . ?
O3 Tb2 O4 52.9(2) 1_654 1_654 ?
O3 Tb2 O12 116.1(2) 1_654 2_443 ?
O3 Tb2 O15 102.8(2) 1_654 . ?
O3 Tb2 C8 26.4(2) 1_654 1_654 ?
O4 Tb2 O12 113.8(2) 1_654 2_443 ?
O4 Tb2 O15 73.2(3) 1_654 . ?
O4 Tb2 C8 26.5(2) 1_654 1_654 ?
O6 Tb2 O3 82.3(2) . 1_654 ?
O6 Tb2 O4 132.0(2) . 1_654 ?
O6 Tb2 O7 78.2(2) . 2_554 ?
O6 Tb2 O10 133.1(2) . . ?
O6 Tb2 O11 78.6(2) . 2_443 ?
O6 Tb2 O12 67.99(19) . 2_443 ?
O6 Tb2 O15 141.4(2) . . ?
O6 Tb2 O16 75.0(2) . . ?
O6 Tb2 C8 107.4(2) . 1_654 ?
O7 Tb2 O3 152.70(19) 2_554 1_654 ?
O7 Tb2 O4 149.7(2) 2_554 1_654 ?
O7 Tb2 O10 75.2(2) 2_554 . ?
O7 Tb2 O11 122.3(2) 2_554 2_443 ?
O7 Tb2 O12 73.66(17) 2_554 2_443 ?
O7 Tb2 O15 81.5(2) 2_554 . ?
O7 Tb2 O16 81.8(2) 2_554 . ?
O7 Tb2 C8 167.8(2) 2_554 1_654 ?
O10 Tb2 O3 131.87(19) . 1_654 ?
O10 Tb2 O4 80.8(2) . 1_654 ?
O10 Tb2 O11 83.9(2) . 2_443 ?
O10 Tb2 O12 67.76(19) . 2_443 ?
O10 Tb2 O15 70.6(2) . . ?
O10 Tb2 O16 136.6(2) . . ?
O10 Tb2 C8 106.5(2) . 1_654 ?
O11 Tb2 O3 71.3(2) 2_443 1_654 ?
O11 Tb2 O4 72.2(3) 2_443 1_654 ?
O11 Tb2 O12 48.68(18) 2_443 2_443 ?
O11 Tb2 O15 139.7(3) 2_443 . ?
O11 Tb2 C8 69.8(2) 2_443 1_654 ?
O12 Tb2 C8 118.3(2) 2_443 1_654 ?
O15 Tb2 O12 135.6(2) . 2_443 ?
O15 Tb2 C8 87.7(3) . 1_654 ?
O16 Tb2 O3 74.8(2) . 1_654 ?
O16 Tb2 O4 104.2(3) . 1_654 ?
O16 Tb2 O11 139.2(2) . 2_443 ?
O16 Tb2 O12 138.8(2) . 2_443 ?
O16 Tb2 O15 69.8(2) . . ?
O16 Tb2 C8 89.2(2) . 1_654 ?
C7 O1 Tb1 95.7(5) . . ?
C7 O2 Tb1 92.3(5) . . ?
C8 O3 Tb2 93.8(5) . 1_456 ?
C8 O4 Tb2 93.4(5) . 1_456 ?
C9 O5 Tb1 134.5(5) . . ?
C9 O6 Tb2 139.4(5) . . ?
Tb2 O7 Tb1 107.5(2) 2_544 2_544 ?
C12 O7 Tb1 90.2(5) . 2_544 ?
C12 O7 Tb2 158.0(5) . 2_544 ?
C12 O8 Tb1 99.3(5) . 2_544 ?
C13 O9 Tb1 137.8(5) . . ?
C13 O10 Tb2 134.8(5) . . ?
C16 O11 Tb2 104.9(5) . 2_453 ?
Tb1 O12 Tb2 101.7(2) 2_453 2_453 ?
C16 O12 Tb1 172.2(6) . 2_453 ?
C16 O12 Tb2 86.1(5) . 2_453 ?
Tb1 O13 H13A 130(6) . . ?
Tb1 O13 H13B 116(7) . . ?
H13A O13 H13B 110(4) . . ?
Tb1 O14 H14A 122(6) . . ?
Tb1 O14 H14B 115(10) . . ?
H14A O14 H14B 109(4) . . ?
Tb2 O15 H15A 109(9) . . ?
Tb2 O15 H15B 137(10) . . ?
H15A O15 H15B 110(4) . . ?
Tb2 O16 H16A 112(6) . . ?
Tb2 O16 H16B 131(8) . . ?
H16A O16 H16B 110(4) . . ?
H17A O17 H17B 110(4) . . ?
H18A O18 H18B 109(4) . . ?
C2 C1 C7 120.3(7) . . ?
C6 C1 C2 118.1(7) . . ?
C6 C1 C7 121.5(7) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 C1 120.9(8) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 H3 120.2 . . ?
C2 C3 C4 119.7(8) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C8 120.6(7) . . ?
C5 C4 C3 120.0(7) . . ?
C5 C4 C8 119.4(7) . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.3(8) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 H6 119.5 . . ?
C5 C6 C1 121.0(8) . . ?
C5 C6 H6 119.5 . . ?
O1 C7 C1 119.9(8) . . ?
O2 C7 O1 119.6(8) . . ?
O2 C7 C1 120.5(7) . . ?
O3 C8 Tb2 59.8(4) . 1_456 ?
O3 C8 O4 119.9(8) . . ?
O3 C8 C4 120.1(8) . . ?
O4 C8 Tb2 60.1(4) . 1_456 ?
O4 C8 C4 120.0(8) . . ?
C4 C8 Tb2 178.2(6) . 1_456 ?
O5 C9 C10 119.1(7) . . ?
O6 C9 O5 126.4(8) . . ?
O6 C9 C10 114.3(7) . . ?
C9 C10 H10 117.0 . . ?
C11 C10 C9 126.1(8) . . ?
C11 C10 H10 117.0 . . ?
C10 C11 H11 119.4 . . ?
C10 C11 C12 121.1(8) . . ?
C12 C11 H11 119.4 . . ?
O7 C12 Tb1 64.0(4) . 2_544 ?
O7 C12 C11 118.8(7) . . ?
O8 C12 Tb1 56.1(4) . 2_544 ?
O8 C12 O7 119.9(8) . . ?
O8 C12 C11 121.3(8) . . ?
C11 C12 Tb1 175.0(6) . 2_544 ?
O9 C13 O10 125.7(7) . . ?
O9 C13 C14 118.2(7) . . ?
O10 C13 C14 116.1(7) . . ?
C13 C14 H14 117.9 . . ?
C15 C14 C13 124.2(8) . . ?
C15 C14 H14 117.9 . . ?
C14 C15 H15 117.7 . . ?
C14 C15 C16 124.5(8) . . ?
C16 C15 H15 117.7 . . ?
O11 C16 Tb2 51.0(4) . 2_453 ?
O11 C16 C15 118.7(7) . . ?
O12 C16 Tb2 69.2(5) . 2_453 ?
O12 C16 O11 119.9(8) . . ?
O12 C16 C15 121.4(8) . . ?
C15 C16 Tb2 167.3(6) . 2_453 ?

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
O13 H13A O17 0.833(15) 1.94(3) 2.744(10) 163(8) .
O14 H14B O17 0.840(15) 2.19(12) 2.880(11) 139(16) .
O16 H16B O18 0.837(15) 1.88(6) 2.671(10) 157(14) .

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
Tb1 O1 C7 O2 -5.4(9) . . . . ?
Tb1 O1 C7 C1 176.2(6) . . . . ?
Tb1 O2 C7 O1 5.2(9) . . . . ?
Tb1 O2 C7 C1 -176.4(7) . . . . ?
Tb1 O5 C9 O6 27.3(13) . . . . ?
Tb1 O5 C9 C10 -149.4(6) . . . . ?
Tb1 O7 C12 O8 -3.9(8) 2_544 . . . ?
Tb1 O7 C12 C11 175.3(7) 2_544 . . . ?
Tb1 O8 C12 O7 4.2(9) 2_544 . . . ?
Tb1 O8 C12 C11 -174.9(7) 2_544 . . . ?
Tb1 O9 C13 O10 11.7(14) . . . . ?
Tb1 O9 C13 C14 -166.0(6) . . . . ?
Tb2 O3 C8 O4 -1.0(9) 1_456 . . . ?
Tb2 O3 C8 C4 177.9(6) 1_456 . . . ?
Tb2 O4 C8 O3 1.0(9) 1_456 . . . ?
Tb2 O4 C8 C4 -178.0(6) 1_456 . . . ?
Tb2 O6 C9 O5 -5.1(15) . . . . ?
Tb2 O6 C9 C10 171.7(6) . . . . ?
Tb2 O7 C12 Tb1 -144.1(15) 2_544 . . 2_544 ?
Tb2 O7 C12 O8 -148.0(11) 2_544 . . . ?
Tb2 O7 C12 C11 31.2(19) 2_544 . . . ?
Tb2 O10 C13 O9 -35.2(13) . . . . ?
Tb2 O10 C13 C14 142.6(6) . . . . ?
Tb2 O11 C16 O12 -7.3(10) 2_453 . . . ?
Tb2 O11 C16 C15 171.0(6) 2_453 . . . ?
Tb2 O12 C16 O11 6.0(8) 2_453 . . . ?
Tb2 O12 C16 C15 -172.2(7) 2_453 . . . ?
O5 C9 C10 C11 -10.9(14) . . . . ?
O6 C9 C10 C11 172.0(9) . . . . ?
O9 C13 C14 C15 4.0(14) . . . . ?
O10 C13 C14 C15 -173.9(9) . . . . ?
C1 C2 C3 C4 -1.3(15) . . . . ?
C2 C1 C6 C5 2.4(14) . . . . ?
C2 C1 C7 O1 6.5(12) . . . . ?
C2 C1 C7 O2 -171.8(9) . . . . ?
C2 C3 C4 C5 3.4(15) . . . . ?
C2 C3 C4 C8 -175.8(8) . . . . ?
C3 C4 C5 C6 -2.7(16) . . . . ?
C3 C4 C8 O3 1.6(12) . . . . ?
C3 C4 C8 O4 -179.4(9) . . . . ?
C4 C5 C6 C1 -0.3(16) . . . . ?
C5 C4 C8 O3 -177.6(9) . . . . ?
C5 C4 C8 O4 1.4(13) . . . . ?
C6 C1 C2 C3 -1.6(14) . . . . ?
C6 C1 C7 O1 -172.4(9) . . . . ?
C6 C1 C7 O2 9.2(13) . . . . ?
C7 C1 C2 C3 179.4(9) . . . . ?
C7 C1 C6 C5 -178.6(9) . . . . ?
C8 C4 C5 C6 176.6(9) . . . . ?
C9 C10 C11 C12 175.2(8) . . . . ?
C10 C11 C12 O7 178.3(8) . . . . ?
C10 C11 C12 O8 -2.6(14) . . . . ?
C13 C14 C15 C16 173.8(8) . . . . ?
C14 C15 C16 Tb2 -143(2) . . . 2_453 ?
C14 C15 C16 O11 -176.7(9) . . . . ?
C14 C15 C16 O12 1.5(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.549(17)
2 0.451(17)

####################################################################### 
# 
# 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_7
_database_code_depnum_ccdc_archive 'CCDC 1863670'
_audit_update_record             
;
2018-08-24 deposited with the CCDC.
2018-09-26 downloaded from the CCDC.
;
_audit_creation_date             2018-04-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.18 svn.r3501 for OlexSys, GUI svn.r5488)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H5 O6 Sm'
_chemical_formula_sum            'C10 H5 O6 Sm'
_chemical_formula_weight         371.49
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sm Sm -0.1638 3.4418 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   14.1351(6)
_cell_length_b                   6.8443(3)
_cell_length_c                   22.0442(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2132.66(16)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5690
_cell_measurement_temperature    296
_cell_measurement_theta_max      25.154
_cell_measurement_theta_min      2.882
_shelx_estimated_absorpt_T_max   0.809
_shelx_estimated_absorpt_T_min   0.512
_exptl_absorpt_coefficient_mu    5.519
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6425
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0830 before and 0.0730 after correction. The Ratio of minimum to maximum transmission is 0.8622. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.314
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1400
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0931
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            27566
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.406
_diffrn_reflns_theta_min         2.882
_diffrn_ambient_temperature      296.0
_diffrn_detector                 'Bruker PHOTON 100 area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'PHOTON area detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'four-circle KAPPA diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_collimation    '0.5 mm'
_diffrn_radiation_monochromator  'graphiteDouble Bounce Multilayer Mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed x-ray tube'
_diffrn_source_target            Cu
_diffrn_source_type              'Incoatec I\mus'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1551
_reflns_number_total             1956
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2016)'
_computing_data_collection       'APEX 3 (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.915
_refine_diff_density_min         -0.925
_refine_diff_density_rms         0.228
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.199
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         1956
_refine_ls_number_restraints     54
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0412
_refine_ls_restrained_S_all      1.182
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0544P)²+4.1054P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0972
_refine_ls_wR_factor_ref         0.1039
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid body (RIGU) restrains
 C3, C4, C5, C6, C7, C8
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
 O1, C1, O2, C2
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C7(H7), C8(H8)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.66848(2) 1.05056(6) 0.55728(2) 0.01218(16) Uani 1 1 d . . . . .
O1 O 0.6693(4) 0.6966(8) 0.5480(2) 0.0223(11) Uani 1 1 d . U . . .
O2 O 0.6713(4) 0.3923(8) 0.5152(3) 0.0192(10) Uani 1 1 d . U . . .
O3 O 0.5122(4) 0.9919(9) 0.5726(2) 0.0249(14) Uani 1 1 d . . . . .
O4 O 0.3610(4) 0.9973(9) 0.5461(2) 0.0227(14) Uani 1 1 d . . . . .
O5 O 0.3735(5) 0.7791(10) 0.8670(3) 0.0394(18) Uani 1 1 d . . . . .
O6 O 0.2382(5) 0.9314(10) 0.8533(3) 0.0329(15) Uani 1 1 d . . . . .
C1 C 0.6271(5) 0.5477(13) 0.5250(4) 0.0173(13) Uani 1 1 d . U . . .
C2 C 0.5260(6) 0.5691(13) 0.5108(5) 0.030(2) Uani 1 1 d . U . . .
H2 H 0.497812 0.689855 0.517740 0.036 Uiso 1 1 calc R . . . .
C3 C 0.3962(6) 0.9653(13) 0.6502(4) 0.0225(15) Uani 1 1 d . U . . .
C4 C 0.4628(6) 0.9055(14) 0.6927(4) 0.031(2) Uani 1 1 d . U . . .
H4 H 0.524985 0.883503 0.680710 0.038 Uiso 1 1 calc R . . . .
C5 C 0.4371(6) 0.8786(15) 0.7525(4) 0.0305(19) Uani 1 1 d . U . . .
H5 H 0.481882 0.838058 0.780778 0.037 Uiso 1 1 calc R . . . .
C6 C 0.3442(6) 0.9122(12) 0.7705(4) 0.0214(15) Uani 1 1 d . U . . .
C7 C 0.2794(6) 0.9746(13) 0.7281(4) 0.0254(17) Uani 1 1 d . U . . .
H7 H 0.217591 1.001530 0.739943 0.030 Uiso 1 1 calc R . . . .
C8 C 0.3050(6) 0.9976(13) 0.6682(4) 0.0257(17) Uani 1 1 d . U . . .
H8 H 0.259857 1.035461 0.639856 0.031 Uiso 1 1 calc R . . . .
C9 C 0.4250(5) 0.9873(11) 0.5853(3) 0.0162(17) Uani 1 1 d . . . . .
C10 C 0.3172(6) 0.8721(13) 0.8350(4) 0.027(2) 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 O1 2.431(6) . ?
Sm1 O1 2.510(5) 8_765 ?
Sm1 O2 2.677(5) 8_765 ?
Sm1 O2 2.517(6) 1_565 ?
Sm1 O3 2.270(6) . ?
Sm1 O4 2.340(5) 5_676 ?
Sm1 O5 2.364(6) 3_656 ?
Sm1 O6 2.350(6) 6_657 ?
Sm1 C1 2.975(7) 8_765 ?
O1 C1 1.285(10) . ?
O2 C1 1.252(10) . ?
O3 C9 1.265(9) . ?
O4 C9 1.252(10) . ?
O5 C10 1.239(11) . ?
O6 C10 1.254(11) . ?
C1 C2 1.471(11) . ?
C2 C2 1.289(17) 5_666 ?
C2 H2 0.9300 . ?
C3 C4 1.390(12) . ?
C3 C8 1.367(12) . ?
C3 C9 1.494(11) . ?
C4 H4 0.9300 . ?
C4 C5 1.381(12) . ?
C5 H5 0.9300 . ?
C5 C6 1.392(11) . ?
C6 C7 1.377(11) . ?
C6 C10 1.498(11) . ?
C7 H7 0.9300 . ?
C7 C8 1.377(12) . ?
C8 H8 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Sm1 O1 112.68(14) . 8_765 ?
O1 Sm1 O2 64.13(17) . 8_765 ?
O1 Sm1 O2 50.19(17) 8_765 8_765 ?
O1 Sm1 O2 153.52(18) . 1_565 ?
O1 Sm1 O2 65.51(17) 8_765 1_565 ?
O1 Sm1 C1 25.3(2) 8_765 8_765 ?
O1 Sm1 C1 88.2(2) . 8_765 ?
O2 Sm1 O2 103.58(16) 1_565 8_765 ?
O2 Sm1 C1 84.42(19) 1_565 8_765 ?
O2 Sm1 C1 24.9(2) 8_765 8_765 ?
O3 Sm1 O1 166.3(2) . 8_765 ?
O3 Sm1 O1 80.8(2) . . ?
O3 Sm1 O2 103.56(19) . 1_565 ?
O3 Sm1 O2 143.4(2) . 8_765 ?
O3 Sm1 O4 86.9(2) . 5_676 ?
O3 Sm1 O5 76.6(2) . 3_656 ?
O3 Sm1 O6 102.8(2) . 6_657 ?
O3 Sm1 C1 168.3(2) . 8_765 ?
O4 Sm1 O1 77.3(2) 5_676 . ?
O4 Sm1 O1 98.0(2) 5_676 8_765 ?
O4 Sm1 O2 76.9(2) 5_676 1_565 ?
O4 Sm1 O2 75.88(19) 5_676 8_765 ?
O4 Sm1 O5 137.4(2) 5_676 3_656 ?
O4 Sm1 O6 147.5(2) 5_676 6_657 ?
O4 Sm1 C1 86.5(2) 5_676 8_765 ?
O5 Sm1 O1 91.3(2) 3_656 8_765 ?
O5 Sm1 O1 136.0(2) 3_656 . ?
O5 Sm1 O2 69.5(2) 3_656 1_565 ?
O5 Sm1 O2 136.5(2) 3_656 8_765 ?
O5 Sm1 C1 114.7(2) 3_656 8_765 ?
O6 Sm1 O1 73.9(2) 6_657 . ?
O6 Sm1 O1 79.8(2) 6_657 8_765 ?
O6 Sm1 O2 128.7(2) 6_657 1_565 ?
O6 Sm1 O2 78.2(2) 6_657 8_765 ?
O6 Sm1 O5 75.1(2) 6_657 3_656 ?
O6 Sm1 C1 77.9(2) 6_657 8_765 ?
Sm1 O1 Sm1 113.2(2) . 8_755 ?
C1 O1 Sm1 98.1(5) . 8_755 ?
C1 O1 Sm1 145.2(5) . . ?
Sm1 O2 Sm1 105.16(18) 1_545 8_755 ?
C1 O2 Sm1 91.0(5) . 8_755 ?
C1 O2 Sm1 135.8(5) . 1_545 ?
C9 O3 Sm1 170.3(6) . . ?
C9 O4 Sm1 142.4(5) . 5_676 ?
C10 O5 Sm1 125.4(6) . 3_646 ?
C10 O6 Sm1 139.1(6) . 6_557 ?
O1 C1 Sm1 56.6(4) . 8_755 ?
O1 C1 C2 117.1(8) . . ?
O2 C1 Sm1 64.1(4) . 8_755 ?
O2 C1 O1 120.7(7) . . ?
O2 C1 C2 122.1(8) . . ?
C2 C1 Sm1 173.7(6) . 8_755 ?
C1 C2 H2 118.0 . . ?
C2 C2 C1 124.0(11) 5_666 . ?
C2 C2 H2 118.0 5_666 . ?
C4 C3 C9 119.4(8) . . ?
C8 C3 C4 119.3(8) . . ?
C8 C3 C9 121.3(8) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.4(8) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.9(8) . . ?
C6 C5 H5 120.1 . . ?
C5 C6 C10 118.7(8) . . ?
C7 C6 C5 119.1(8) . . ?
C7 C6 C10 122.2(8) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 C6 120.8(8) . . ?
C8 C7 H7 119.6 . . ?
C3 C8 C7 120.6(8) . . ?
C3 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
O3 C9 C3 118.7(7) . . ?
O4 C9 O3 123.3(7) . . ?
O4 C9 C3 117.9(7) . . ?
O5 C10 O6 123.7(8) . . ?
O5 C10 C6 118.1(8) . . ?
O6 C10 C6 118.2(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
C2 H2 O3 0.93 2.40 3.204(11) 144.2 .

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
Sm1 O1 C1 Sm1 154.4(9) . . . 8_755 ?
Sm1 O1 C1 O2 154.8(6) . . . . ?
Sm1 O1 C1 O2 0.4(8) 8_755 . . . ?
Sm1 O1 C1 C2 -24.9(13) . . . . ?
Sm1 O1 C1 C2 -179.3(7) 8_755 . . . ?
Sm1 O2 C1 Sm1 113.2(6) 1_545 . . 8_755 ?
Sm1 O2 C1 O1 -0.4(8) 8_755 . . . ?
Sm1 O2 C1 O1 112.9(8) 1_545 . . . ?
Sm1 O2 C1 C2 -67.5(11) 1_545 . . . ?
Sm1 O2 C1 C2 179.3(8) 8_755 . . . ?
Sm1 O4 C9 O3 21.3(15) 5_676 . . . ?
Sm1 O4 C9 C3 -157.6(7) 5_676 . . . ?
Sm1 O5 C10 O6 34.5(12) 3_646 . . . ?
Sm1 O5 C10 C6 -144.2(6) 3_646 . . . ?
Sm1 O6 C10 O5 34.6(15) 6_557 . . . ?
Sm1 O6 C10 C6 -146.7(7) 6_557 . . . ?
O1 C1 C2 C2 -177.9(13) . . . 5_666 ?
O2 C1 C2 C2 2.4(19) . . . 5_666 ?
C3 C4 C5 C6 -0.3(15) . . . . ?
C4 C3 C8 C7 1.1(14) . . . . ?
C4 C3 C9 O3 -14.9(13) . . . . ?
C4 C3 C9 O4 164.1(8) . . . . ?
C4 C5 C6 C7 -0.8(14) . . . . ?
C4 C5 C6 C10 176.9(9) . . . . ?
C5 C6 C7 C8 2.1(14) . . . . ?
C5 C6 C10 O5 -12.4(13) . . . . ?
C5 C6 C10 O6 168.8(9) . . . . ?
C6 C7 C8 C3 -2.2(15) . . . . ?
C7 C6 C10 O5 165.3(9) . . . . ?
C7 C6 C10 O6 -13.5(13) . . . . ?
C8 C3 C4 C5 0.1(15) . . . . ?
C8 C3 C9 O3 167.0(8) . . . . ?
C8 C3 C9 O4 -14.1(13) . . . . ?
C9 C3 C4 C5 -178.1(9) . . . . ?
C9 C3 C8 C7 179.3(9) . . . . ?
C10 C6 C7 C8 -175.6(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_10
_database_code_depnum_ccdc_archive 'CCDC 1863673'
_audit_update_record             
;
2018-08-24 deposited with the CCDC.
2018-09-26 downloaded from the CCDC.
;
_audit_creation_date             2018-02-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H5 Er O6'
_chemical_formula_sum            'C10 H5 Er O6'
_chemical_formula_weight         388.40
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Er Er -0.2586 4.9576 '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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   13.9332(16)
_cell_length_b                   6.7258(8)
_cell_length_c                   21.795(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2042.4(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9923
_cell_measurement_temperature    296
_cell_measurement_theta_max      31.526
_cell_measurement_theta_min      2.924
_shelx_estimated_absorpt_T_max   0.734
_shelx_estimated_absorpt_T_min   0.290
_exptl_absorpt_coefficient_mu    8.231
_exptl_absorpt_correction_T_max  0.2671
_exptl_absorpt_correction_T_min  0.1502
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1108 before and 0.0438 after correction. The Ratio of minimum to maximum transmission is 0.5623. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.526
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1448
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            23356
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.543
_diffrn_reflns_theta_min         3.471
_diffrn_ambient_temperature      296.0
_diffrn_detector                 'Bruker PHOTON 100 area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'PHOTON area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'four-circle KAPPA diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_collimation    '0.5 mm'
_diffrn_radiation_monochromator  'graphiteDouble Bounce Multilayer Mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed x-ray tube'
_diffrn_source_target            Cu
_diffrn_source_type              'Incoatec I\mus'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2952
_reflns_number_total             3398
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         2.311
_refine_diff_density_min         -0.839
_refine_diff_density_rms         0.141
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         3398
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0232
_refine_ls_restrained_S_all      1.104
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0219P)²+2.8745P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0486
_refine_ls_wR_factor_ref         0.0504
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C7(H7), C8(H8)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.66955(2) 1.04947(2) 0.55648(2) 0.01428(4) Uani 1 1 d . . . . .
O1 O 0.67194(12) 0.6960(3) 0.54864(10) 0.0235(4) Uani 1 1 d . . . . .
O2 O 0.67353(12) 0.3914(3) 0.51446(10) 0.0221(4) Uani 1 1 d . . . . .
O3 O 0.51562(14) 0.9917(4) 0.57186(10) 0.0258(4) Uani 1 1 d . . . . .
O4 O 0.36288(15) 0.9955(4) 0.54430(9) 0.0241(4) Uani 1 1 d . . . . .
O5 O 0.37298(16) 0.7775(4) 0.86958(9) 0.0312(5) Uani 1 1 d . . . . .
O6 O 0.23529(16) 0.9366(3) 0.85461(9) 0.0289(5) Uani 1 1 d . . . . .
C1 C 0.62891(17) 0.5484(4) 0.52481(13) 0.0198(5) Uani 1 1 d . . . . .
C2 C 0.5266(2) 0.5705(5) 0.50967(19) 0.0373(9) Uani 1 1 d . . . . .
H2 H 0.498856 0.695332 0.514512 0.045 Uiso 1 1 calc R . . . .
C3 C 0.39897(18) 0.9629(4) 0.64976(12) 0.0191(5) Uani 1 1 d . . . . .
C4 C 0.4664(2) 0.9076(5) 0.69353(13) 0.0302(7) Uani 1 1 d . . . . .
H4 H 0.530111 0.889211 0.682166 0.036 Uiso 1 1 calc R . . . .
C5 C 0.4390(2) 0.8796(6) 0.75410(13) 0.0313(7) Uani 1 1 d . . . . .
H5 H 0.483939 0.839180 0.783070 0.038 Uiso 1 1 calc R . . . .
C6 C 0.3445(2) 0.9122(4) 0.77139(12) 0.0221(5) Uani 1 1 d . . . . .
C7 C 0.2773(2) 0.9710(5) 0.72828(13) 0.0277(6) Uani 1 1 d . . . . .
H7 H 0.214258 0.995235 0.740080 0.033 Uiso 1 1 calc R . . . .
C8 C 0.3042(2) 0.9935(5) 0.66765(13) 0.0243(6) Uani 1 1 d . . . . .
H8 H 0.258604 1.029380 0.638537 0.029 Uiso 1 1 calc R . . . .
C9 C 0.42766(18) 0.9862(4) 0.58429(11) 0.0173(5) Uani 1 1 d . . . . .
C10 C 0.3153(2) 0.8730(5) 0.83648(12) 0.0235(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
Er1 O1 2.384(2) . ?
Er1 O1 2.4244(18) 8_765 ?
Er1 O2 2.5979(19) 8_765 ?
Er1 O2 2.476(2) 1_565 ?
Er1 O3 2.2053(19) . ?
Er1 O4 2.263(2) 5_676 ?
Er1 O5 2.302(2) 3_656 ?
Er1 O6 2.274(2) 6_657 ?
Er1 C1 2.892(2) 8_765 ?
O1 C1 1.271(3) . ?
O2 C1 1.246(3) . ?
O3 C9 1.256(3) . ?
O4 C9 1.256(3) . ?
O5 C10 1.257(4) . ?
O6 C10 1.258(3) . ?
C1 C2 1.471(4) . ?
C2 C2 1.275(6) 5_666 ?
C2 H2 0.9300 . ?
C3 C4 1.389(4) . ?
C3 C8 1.392(4) . ?
C3 C9 1.490(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.387(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.387(4) . ?
C6 C7 1.384(4) . ?
C6 C10 1.499(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.382(4) . ?
C8 H8 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Er1 O1 112.80(5) . 8_765 ?
O1 Er1 O2 63.57(6) . 8_765 ?
O1 Er1 O2 51.30(7) 8_765 8_765 ?
O1 Er1 O2 154.09(7) . 1_565 ?
O1 Er1 O2 64.92(6) 8_765 1_565 ?
O1 Er1 C1 25.78(7) 8_765 8_765 ?
O1 Er1 C1 88.10(7) . 8_765 ?
O2 Er1 O2 103.35(6) 1_565 8_765 ?
O2 Er1 C1 83.82(7) 1_565 8_765 ?
O2 Er1 C1 25.52(7) 8_765 8_765 ?
O3 Er1 O1 165.53(8) . 8_765 ?
O3 Er1 O1 81.30(8) . . ?
O3 Er1 O2 103.98(7) . 1_565 ?
O3 Er1 O2 143.13(8) . 8_765 ?
O3 Er1 O4 85.98(8) . 5_676 ?
O3 Er1 O5 76.16(8) . 3_656 ?
O3 Er1 O6 101.74(8) . 6_657 ?
O3 Er1 C1 168.60(8) . 8_765 ?
O4 Er1 O1 78.46(8) 5_676 . ?
O4 Er1 O1 99.65(7) 5_676 8_765 ?
O4 Er1 O2 76.68(8) 5_676 1_565 ?
O4 Er1 O2 76.77(7) 5_676 8_765 ?
O4 Er1 O5 135.81(8) 5_676 3_656 ?
O4 Er1 O6 149.66(8) 5_676 6_657 ?
O4 Er1 C1 87.81(8) 5_676 8_765 ?
O5 Er1 O1 90.75(8) 3_656 8_765 ?
O5 Er1 O1 135.91(8) 3_656 . ?
O5 Er1 O2 69.26(8) 3_656 1_565 ?
O5 Er1 O2 137.39(7) 3_656 8_765 ?
O5 Er1 C1 114.75(8) 3_656 8_765 ?
O6 Er1 O1 73.88(7) 6_657 . ?
O6 Er1 O1 80.15(8) 6_657 8_765 ?
O6 Er1 O2 128.05(7) 6_657 1_565 ?
O6 Er1 O2 79.90(7) 6_657 8_765 ?
O6 Er1 O5 74.32(8) 6_657 3_656 ?
O6 Er1 C1 79.13(8) 6_657 8_765 ?
Er1 O1 Er1 114.40(7) . 8_755 ?
C1 O1 Er1 98.12(16) . 8_755 ?
C1 O1 Er1 143.30(17) . . ?
Er1 O2 Er1 105.58(7) 1_545 8_755 ?
C1 O2 Er1 90.54(16) . 8_755 ?
C1 O2 Er1 135.16(18) . 1_545 ?
C9 O3 Er1 170.8(2) . . ?
C9 O4 Er1 144.12(18) . 5_676 ?
C10 O5 Er1 125.29(19) . 3_646 ?
C10 O6 Er1 137.59(19) . 6_557 ?
O1 C1 Er1 56.10(12) . 8_755 ?
O1 C1 C2 118.0(3) . . ?
O2 C1 Er1 63.94(13) . 8_755 ?
O2 C1 O1 120.0(2) . . ?
O2 C1 C2 121.9(3) . . ?
C2 C1 Er1 174.0(2) . 8_755 ?
C1 C2 H2 117.9 . . ?
C2 C2 C1 124.2(4) 5_666 . ?
C2 C2 H2 117.9 5_666 . ?
C4 C3 C8 119.2(2) . . ?
C4 C3 C9 120.3(2) . . ?
C8 C3 C9 120.5(2) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.2(3) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 119.9(3) . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C10 119.2(3) . . ?
C7 C6 C5 120.2(2) . . ?
C7 C6 C10 120.6(3) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 C6 119.8(3) . . ?
C8 C7 H7 120.1 . . ?
C3 C8 H8 119.7 . . ?
C7 C8 C3 120.6(3) . . ?
C7 C8 H8 119.7 . . ?
O3 C9 O4 123.4(2) . . ?
O3 C9 C3 118.1(2) . . ?
O4 C9 C3 118.5(2) . . ?
O5 C10 O6 124.1(3) . . ?
O5 C10 C6 117.3(3) . . ?
O6 C10 C6 118.6(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
C2 H2 O3 0.93 2.36 3.144(4) 141.3 .

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
Er1 O1 C1 Er1 152.8(3) . . . 8_755 ?
Er1 O1 C1 O2 153.7(2) . . . . ?
Er1 O1 C1 O2 0.9(3) 8_755 . . . ?
Er1 O1 C1 C2 -178.5(3) 8_755 . . . ?
Er1 O1 C1 C2 -25.7(5) . . . . ?
Er1 O2 C1 Er1 113.0(2) 1_545 . . 8_755 ?
Er1 O2 C1 O1 112.1(3) 1_545 . . . ?
Er1 O2 C1 O1 -0.8(3) 8_755 . . . ?
Er1 O2 C1 C2 178.6(3) 8_755 . . . ?
Er1 O2 C1 C2 -68.5(4) 1_545 . . . ?
Er1 O4 C9 O3 21.2(5) 5_676 . . . ?
Er1 O4 C9 C3 -157.4(2) 5_676 . . . ?
Er1 O5 C10 O6 36.2(4) 3_646 . . . ?
Er1 O5 C10 C6 -143.6(2) 3_646 . . . ?
Er1 O6 C10 O5 31.8(5) 6_557 . . . ?
Er1 O6 C10 C6 -148.3(2) 6_557 . . . ?
O1 C1 C2 C2 -174.0(5) . . . 5_666 ?
O2 C1 C2 C2 6.5(8) . . . 5_666 ?
C3 C4 C5 C6 -1.7(6) . . . . ?
C4 C3 C8 C7 0.6(5) . . . . ?
C4 C3 C9 O3 -13.2(4) . . . . ?
C4 C3 C9 O4 165.5(3) . . . . ?
C4 C5 C6 C7 0.5(5) . . . . ?
C4 C5 C6 C10 177.5(3) . . . . ?
C5 C6 C7 C8 1.3(5) . . . . ?
C5 C6 C10 O5 -13.1(4) . . . . ?
C5 C6 C10 O6 167.1(3) . . . . ?
C6 C7 C8 C3 -1.8(5) . . . . ?
C7 C6 C10 O5 163.9(3) . . . . ?
C7 C6 C10 O6 -16.0(4) . . . . ?
C8 C3 C4 C5 1.2(5) . . . . ?
C8 C3 C9 O3 167.7(3) . . . . ?
C8 C3 C9 O4 -13.6(4) . . . . ?
C9 C3 C4 C5 -177.9(3) . . . . ?
C9 C3 C8 C7 179.7(3) . . . . ?
C10 C6 C7 C8 -175.7(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_12gd
_database_code_depnum_ccdc_archive 'CCDC 1863675'
_audit_update_record             
;
2018-08-24 deposited with the CCDC.
2018-09-26 downloaded from the CCDC.
;
_audit_creation_date             2018-08-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C9 H8 Gd O8, 0.7(H2 O1)'
_chemical_formula_sum            'C9 H9.40 Gd O8.70'
_chemical_formula_weight         414.02
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Gd Gd -0.1653 3.9035 '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'

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

_cell_length_a                   8.3194(7)
_cell_length_b                   18.7938(15)
_cell_length_c                   7.8274(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.066(2)
_cell_angle_gamma                90.00
_cell_volume                     1176.04(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9043
_cell_measurement_temperature    296
_cell_measurement_theta_max      28.293
_cell_measurement_theta_min      2.92
_exptl_absorpt_coefficient_mu    5.677
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5135
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1125 before and 0.0482 after correction. The Ratio of minimum to maximum transmission is 0.6886. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            'light orange'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    2.338
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             788
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0162
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            30909
_diffrn_reflns_theta_full        28.32
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         2.92
_diffrn_ambient_temperature      296
_diffrn_detector                 'Bruker PHOTON 100 area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'PHOTON area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'four-circle KAPPA diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_collimation    '0.5 mm'
_diffrn_radiation_monochromator  'graphiteDouble Bounce Multilayer Mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed x-ray tube'
_diffrn_source_type              'Incoatec I\mus'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                2724
_reflns_number_total             2924
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.862
_refine_diff_density_min         -0.528
_refine_diff_density_rms         0.094
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2924
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0219
_refine_ls_R_factor_gt           0.0186
_refine_ls_restrained_S_all      1.111
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0121P)²+1.9032P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0385
_refine_ls_wR_factor_ref         0.0395
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 O9-H9A = O9-H9B
 0.85 with sigma of 0.02
 O7-H7A = O7-H7B = O8-H8A
 0.84 with sigma of 0.01
 O8-H8B
 0.84 with sigma of 0.01
 H9A-H9B
 1.34 with sigma of 0.04
3. Others
 Fixed Sof: O9(0.7) H9A(0.7) H9B(0.7)
4.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Gd1 Gd 0.244356(13) 0.519607(6) 0.760626(14) 0.01474(4) Uani 1 d . . .
O1 O 0.1677(2) 0.44444(10) 0.5204(2) 0.0284(4) Uani 1 d . . .
O2 O -0.0208(2) 0.39841(10) 0.2894(3) 0.0282(4) Uani 1 d . . .
O3 O 0.6025(2) 0.12287(10) 0.6269(3) 0.0276(4) Uani 1 d . . .
O4 O 0.3877(2) 0.07226(10) 0.4340(3) 0.0287(4) Uani 1 d . . .
O5 O 0.1983(2) 0.53876(10) 1.0522(2) 0.0240(4) Uani 1 d . . .
O6 O 0.0022(2) 0.54386(10) 1.1972(2) 0.0204(4) Uani 1 d . . .
O7 O 0.2488(3) 0.59323(13) 0.4972(3) 0.0335(5) Uani 1 d . . D
O8 O 0.5137(3) 0.50471(14) 0.6864(3) 0.0335(5) Uani 1 d . . D
C1 C 0.2073(3) 0.32609(13) 0.4359(3) 0.0202(5) Uani 1 d . . .
C2 C 0.3687(3) 0.32149(14) 0.5446(4) 0.0260(6) Uani 1 d . . .
H2 H 0.4228 0.3621 0.5999 0.031 Uiso 1 calc . . R
C3 C 0.4506(3) 0.25652(14) 0.5717(4) 0.0262(6) Uani 1 d . . .
H3 H 0.5597 0.2538 0.6447 0.031 Uiso 1 calc . . R
C4 C 0.3712(3) 0.19551(13) 0.4908(3) 0.0199(5) Uani 1 d . . .
C5 C 0.2090(3) 0.20005(15) 0.3806(4) 0.0296(6) Uani 1 d . . .
H5 H 0.1547 0.1594 0.3257 0.036 Uiso 1 calc . . R
C6 C 0.1281(4) 0.26507(15) 0.3523(4) 0.0309(6) Uani 1 d . . .
H6 H 0.0202 0.2681 0.2769 0.037 Uiso 1 calc . . R
C7 C 0.1118(3) 0.39473(13) 0.4128(3) 0.0198(5) Uani 1 d . . .
C8 C 0.4594(3) 0.12511(13) 0.5187(3) 0.0194(5) Uani 1 d . . .
C9 C 0.0580(3) 0.52413(13) 1.0721(3) 0.0175(5) Uani 1 d . . .
O9 O 0.2086(7) 0.7599(4) 0.5261(8) 0.0936(17) Uani 0.70 d . . D
H9A H 0.152(10) 0.740(5) 0.593(9) 0.140 Uiso 0.70 d . . DR
H9B H 0.144(10) 0.749(5) 0.419(5) 0.140 Uiso 0.70 d . . DR
H7A H 0.251(6) 0.6374(6) 0.506(6) 0.074(15) Uiso 1 d . . D
H7B H 0.176(4) 0.585(2) 0.401(3) 0.051(11) Uiso 1 d . . D
H8A H 0.600(3) 0.488(2) 0.756(5) 0.067(14) Uiso 1 d . . D
H8B H 0.549(8) 0.537(3) 0.633(8) 0.15(3) Uiso 1 d . . 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 O1 2.2967(18) . ?
Gd1 O2 2.3627(18) 3_566 ?
Gd1 O3 2.3545(18) 2_656 ?
Gd1 O4 2.3129(18) 4_566 ?
Gd1 O5 2.4430(18) . ?
Gd1 O6 2.4722(17) 3_567 ?
Gd1 O7 2.492(2) . ?
Gd1 O8 2.481(2) . ?
O1 C7 1.258(3) . ?
O2 Gd1 2.3627(18) 3_566 ?
O2 C7 1.251(3) . ?
O3 Gd1 2.3544(18) 2_646 ?
O3 C8 1.257(3) . ?
O4 Gd1 2.3130(18) 4_565 ?
O4 C8 1.250(3) . ?
O5 C9 1.250(3) . ?
O6 Gd1 2.4722(17) 3_567 ?
O6 C9 1.251(3) . ?
O7 H7A 0.833(10) . ?
O7 H7B 0.839(10) . ?
O8 H8A 0.835(10) . ?
O8 H8B 0.838(10) . ?
C1 C2 1.379(3) . ?
C1 C6 1.392(4) . ?
C1 C7 1.499(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.386(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.386(4) . ?
C4 C5 1.389(4) . ?
C4 C8 1.499(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.383(4) . ?
C6 H6 0.9300 . ?
C9 C9 1.558(5) 3_567 ?
O9 H9A 0.88(2) . ?
O9 H9B 0.88(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Gd1 O2 103.77(7) . 3_566 ?
O1 Gd1 O3 144.30(7) . 2_656 ?
O1 Gd1 O4 90.15(7) . 4_566 ?
O1 Gd1 O5 140.87(7) . . ?
O1 Gd1 O6 76.10(7) . 3_567 ?
O1 Gd1 O7 74.24(7) . . ?
O1 Gd1 O8 78.64(7) . . ?
O2 Gd1 O5 74.87(7) 3_566 . ?
O2 Gd1 O6 72.11(7) 3_566 3_567 ?
O2 Gd1 O7 72.07(7) 3_566 . ?
O2 Gd1 O8 139.04(8) 3_566 . ?
O3 Gd1 O2 81.02(7) 2_656 3_566 ?
O3 Gd1 O5 74.79(7) 2_656 . ?
O3 Gd1 O6 136.95(6) 2_656 3_567 ?
O3 Gd1 O7 73.82(7) 2_656 . ?
O3 Gd1 O8 75.55(8) 2_656 . ?
O4 Gd1 O2 146.98(7) 4_566 3_566 ?
O4 Gd1 O3 104.96(7) 4_566 2_656 ?
O4 Gd1 O5 75.56(7) 4_566 . ?
O4 Gd1 O6 82.75(7) 4_566 3_567 ?
O4 Gd1 O7 140.95(8) 4_566 . ?
O4 Gd1 O8 72.58(8) 4_566 . ?
O5 Gd1 O6 66.18(6) . 3_567 ?
O5 Gd1 O7 137.16(7) . . ?
O5 Gd1 O8 128.36(6) . . ?
O6 Gd1 O7 125.53(6) 3_567 . ?
O6 Gd1 O8 144.39(7) 3_567 . ?
O8 Gd1 O7 69.37(8) . . ?
C7 O1 Gd1 166.58(19) . . ?
C7 O2 Gd1 130.51(17) . 3_566 ?
C8 O3 Gd1 126.40(17) . 2_646 ?
C8 O4 Gd1 175.63(18) . 4_565 ?
C9 O5 Gd1 118.52(15) . . ?
C9 O6 Gd1 117.59(15) . 3_567 ?
Gd1 O7 H7A 120(3) . . ?
Gd1 O7 H7B 117(3) . . ?
H7A O7 H7B 105(4) . . ?
Gd1 O8 H8A 124(3) . . ?
Gd1 O8 H8B 120(5) . . ?
H8A O8 H8B 104(5) . . ?
C2 C1 C6 119.4(2) . . ?
C2 C1 C7 121.4(2) . . ?
C6 C1 C7 119.1(2) . . ?
C1 C2 H2 119.9 . . ?
C1 C2 C3 120.2(2) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.5(2) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C5 119.4(2) . . ?
C3 C4 C8 120.8(2) . . ?
C5 C4 C8 119.8(2) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 120.0(3) . . ?
C6 C5 H5 120.0 . . ?
C1 C6 H6 119.8 . . ?
C5 C6 C1 120.5(2) . . ?
C5 C6 H6 119.8 . . ?
O1 C7 C1 118.2(2) . . ?
O2 C7 O1 124.0(2) . . ?
O2 C7 C1 117.7(2) . . ?
O3 C8 C4 117.5(2) . . ?
O4 C8 O3 123.7(2) . . ?
O4 C8 C4 118.8(2) . . ?
O5 C9 O6 126.5(2) . . ?
O5 C9 C9 116.7(3) . 3_567 ?
O6 C9 C9 116.8(3) . 3_567 ?
H9A O9 H9B 101(4) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O7 H7A O9 0.833(10) 2.341(15) 3.165(8) 170(4) .
O7 H7B O6 0.839(10) 1.988(13) 2.814(3) 168(4) 1_554
O8 H8A O5 0.835(10) 1.980(13) 2.808(3) 170(4) 3_667

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
Gd1 O1 C7 O2 101.9(7) . . . . ?
Gd1 O1 C7 C1 -76.6(8) . . . . ?
Gd1 O2 C7 O1 -15.0(4) 3_566 . . . ?
Gd1 O2 C7 C1 163.46(17) 3_566 . . . ?
Gd1 O3 C8 O4 -11.4(4) 2_646 . . . ?
Gd1 O3 C8 C4 168.69(16) 2_646 . . . ?
Gd1 O4 C8 O3 -152(2) 4_565 . . . ?
Gd1 O4 C8 C4 28(3) 4_565 . . . ?
Gd1 O5 C9 O6 -164.1(2) . . . . ?
Gd1 O5 C9 C9 16.6(3) . . . 3_567 ?
Gd1 O6 C9 O5 -164.0(2) 3_567 . . . ?
Gd1 O6 C9 C9 15.3(3) 3_567 . . 3_567 ?
O1 Gd1 O5 C9 -33.8(2) . . . . ?
O2 Gd1 O1 C7 -93.5(8) 3_566 . . . ?
O2 Gd1 O5 C9 59.51(18) 3_566 . . . ?
O3 Gd1 O1 C7 172.7(7) 2_656 . . . ?
O3 Gd1 O5 C9 144.11(19) 2_656 . . . ?
O4 Gd1 O1 C7 56.2(8) 4_566 . . . ?
O4 Gd1 O5 C9 -105.63(19) 4_566 . . . ?
O5 Gd1 O1 C7 -10.7(8) . . . . ?
O6 Gd1 O1 C7 -26.3(7) 3_567 . . . ?
O6 Gd1 O5 C9 -17.28(17) 3_567 . . . ?
O7 Gd1 O1 C7 -160.1(8) . . . . ?
O7 Gd1 O5 C9 100.0(2) . . . . ?
O8 Gd1 O1 C7 128.4(8) . . . . ?
O8 Gd1 O5 C9 -158.90(18) . . . . ?
C1 C2 C3 C4 -0.3(4) . . . . ?
C2 C1 C6 C5 1.3(5) . . . . ?
C2 C1 C7 O1 -14.1(4) . . . . ?
C2 C1 C7 O2 167.4(3) . . . . ?
C2 C3 C4 C5 0.7(4) . . . . ?
C2 C3 C4 C8 179.6(3) . . . . ?
C3 C4 C5 C6 0.0(4) . . . . ?
C3 C4 C8 O3 4.7(4) . . . . ?
C3 C4 C8 O4 -175.2(3) . . . . ?
C4 C5 C6 C1 -1.0(5) . . . . ?
C5 C4 C8 O3 -176.3(3) . . . . ?
C5 C4 C8 O4 3.8(4) . . . . ?
C6 C1 C2 C3 -0.7(4) . . . . ?
C6 C1 C7 O1 162.9(3) . . . . ?
C6 C1 C7 O2 -15.6(4) . . . . ?
C7 C1 C2 C3 176.2(3) . . . . ?
C7 C1 C6 C5 -175.7(3) . . . . ?
C8 C4 C5 C6 -179.0(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
