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

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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1508176'
_audit_update_record             
;
2016-11-03 deposited with the CCDC.
2016-11-14 downloaded from the CCDC.
;
_audit_creation_date             2016-10-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H2 Gd O9, 0.5(C10 H26 N2 O4)'
_chemical_formula_sum            'C9 H15 Gd N O11'
_chemical_formula_weight         470.47
_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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.3203(7)
_cell_length_b                   11.7949(8)
_cell_length_c                   11.5472(7)
_cell_angle_alpha                90
_cell_angle_beta                 105.129(2)
_cell_angle_gamma                90
_cell_volume                     1356.89(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    9524
_cell_measurement_theta_min      6.16
_cell_measurement_theta_max      54.96
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.949
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5142
_exptl_absorpt_correction_T_max  0.5835
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5)
multi-scan from symmetry-related measurements
Sortav (Blessing 1995, 1997)
;
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.303
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0584
_diffrn_reflns_av_unetI/netI     0.0640
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10499
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_min         3.530
_diffrn_ambient_temperature      153(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2788
_reflns_number_total             3071
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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         2.952
_refine_diff_density_min         -1.621
_refine_diff_density_rms         0.201
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3071
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0353
_refine_ls_restrained_S_all      1.044
_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)+(0.0307P)²+4.1310P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0824
_refine_ls_wR_factor_ref         0.0844
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2.a Rotating group:
 O1W(H1WA,H1WB)
2.b Ternary CH refined with riding coordinates:
 N1(H1A)
2.c Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C1(H1B,H1C), C5(H5A,H5B)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O00G(H00G)
;
_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
Gd1 Gd 0.24714(2) 0.34850(2) -0.01694(2) 0.01031(10) Uani 1 1 d . . . . .
O002 O 0.3051(3) 0.3171(3) 0.3753(3) 0.0143(6) Uani 1 1 d . . . . .
O5X O 0.0833(3) 0.3929(3) 0.0947(3) 0.0184(7) Uani 1 1 d . . . . .
O1X O 0.3494(3) 0.3788(3) 0.2048(3) 0.0187(7) Uani 1 1 d . . . . .
O3X O 0.4868(3) 0.3522(3) 0.0063(3) 0.0167(7) Uani 1 1 d . . . . .
O1W O 0.0433(3) 0.2466(3) -0.1195(3) 0.0196(7) Uani 1 1 d . . . . .
H1WA H -0.0247 0.2653 -0.0904 0.029 Uiso 1 1 d GR . . . .
H1WB H 0.0553 0.1727 -0.1108 0.029 Uiso 1 1 d GR . . . .
O007 O 0.2634(3) 0.1094(3) 0.2815(3) 0.0168(7) Uani 1 1 d . . . . .
O2X O 0.2675(3) 0.1782(3) 0.1017(3) 0.0170(7) Uani 1 1 d . . . . .
O4X O 0.6605(3) 0.4604(3) -0.0085(3) 0.0164(7) Uani 1 1 d . . . . .
O6X O -0.0795(3) 0.5105(3) 0.1153(3) 0.0143(6) Uani 1 1 d . . . . .
C2W C 0.2772(4) 0.1869(4) 0.2121(4) 0.0134(9) Uani 1 1 d . . . . .
O1 O 0.0218(4) 0.4824(3) 0.3540(3) 0.0210(7) Uani 1 1 d . . . . .
H1 H -0.0101 0.4796 0.2812 0.031 Uiso 1 1 calc GR . . . .
C3W C 0.0016(4) 0.4714(4) 0.0611(4) 0.0127(9) Uani 1 1 d . . . . .
C1W C 0.3122(4) 0.3064(4) 0.2689(4) 0.0119(8) Uani 1 1 d . . . . .
C4W C 0.5422(4) 0.4459(4) -0.0008(4) 0.0139(9) Uani 1 1 d . . . . .
O00G O 0.2184(4) 0.7748(3) 0.5855(4) 0.0352(10) Uani 1 1 d . . . . .
H00G H 0.2443 0.8364 0.5671 0.053 Uiso 1 1 calc GR . . . .
N1 N 0.3146(4) 0.5383(4) 0.4802(4) 0.0231(9) Uani 1 1 d . . . . .
H1A H 0.2847 0.4592 0.4719 0.028 Uiso 1 1 calc R . . . .
C2 C 0.2188(5) 0.6052(5) 0.3826(4) 0.0192(10) Uani 1 1 d . . . . .
H2A H 0.2270 0.5794 0.3051 0.023 Uiso 1 1 calc R . . . .
H2B H 0.2438 0.6846 0.3906 0.023 Uiso 1 1 calc R . . . .
C3 C 0.3088(6) 0.5793(5) 0.6088(5) 0.0328(13) Uani 1 1 d . . . . .
H3A H 0.2210 0.5608 0.6191 0.039 Uiso 1 1 calc R . . . .
H3B H 0.3744 0.5363 0.6680 0.039 Uiso 1 1 calc R . . . .
C4 C 0.3340(6) 0.7023(5) 0.6356(5) 0.0314(13) Uani 1 1 d . . . . .
H4A H 0.3610 0.7125 0.7219 0.038 Uiso 1 1 calc R . . . .
H4B H 0.4080 0.7266 0.6042 0.038 Uiso 1 1 calc R . . . .
C1 C 0.0741(5) 0.5934(4) 0.3870(4) 0.0219(10) Uani 1 1 d . . . . .
H1B H 0.0678 0.6101 0.4675 0.026 Uiso 1 1 calc R . . . .
H1C H 0.0197 0.6484 0.3331 0.026 Uiso 1 1 calc R . . . .
C5 C 0.4532(5) 0.5416(5) 0.4599(5) 0.0256(11) Uani 1 1 d . . . . .
H5A H 0.4896 0.6176 0.4757 0.031 Uiso 1 1 calc R . . . .
H5B H 0.4472 0.5238 0.3767 0.031 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Gd1 O002 2.472(3) 4_565 ?
Gd1 O5X 2.436(3) . ?
Gd1 O1X 2.528(3) . ?
Gd1 O3X 2.418(3) . ?
Gd1 O1W 2.444(3) . ?
Gd1 O007 2.428(3) 4_565 ?
Gd1 O2X 2.409(3) . ?
Gd1 O4X 2.435(3) 3_665 ?
Gd1 O6X 2.454(3) 3_565 ?
O002 Gd1 2.472(3) 4_566 ?
O002 C1W 1.256(5) . ?
O5X C3W 1.245(5) . ?
O1X C1W 1.254(6) . ?
O3X C4W 1.256(6) . ?
O1W H1WA 0.8823 . ?
O1W H1WB 0.8818 . ?
O007 Gd1 2.428(3) 4_566 ?
O007 C2W 1.248(6) . ?
O2X C2W 1.257(5) . ?
O4X Gd1 2.435(3) 3_665 ?
O4X C4W 1.259(6) . ?
O6X Gd1 2.454(3) 3_565 ?
O6X C3W 1.256(5) . ?
C2W C1W 1.557(6) . ?
O1 H1 0.8200 . ?
O1 C1 1.429(6) . ?
C3W C3W 1.557(8) 3_565 ?
C4W C4W 1.547(9) 3_665 ?
O00G H00G 0.8200 . ?
O00G C4 1.459(7) . ?
N1 H1A 0.9800 . ?
N1 C2 1.513(6) . ?
N1 C3 1.578(7) . ?
N1 C5 1.510(7) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C1 1.514(7) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.492(9) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C1 H1B 0.9700 . ?
C1 H1C 0.9700 . ?
C5 C5 1.513(10) 3_666 ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?

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
O002 Gd1 O1X 121.98(11) 4_565 . ?
O5X Gd1 O002 136.79(11) . 4_565 ?
O5X Gd1 O1X 66.27(11) . . ?
O5X Gd1 O1W 74.55(11) . . ?
O5X Gd1 O6X 66.20(10) . 3_565 ?
O3X Gd1 O002 72.25(11) . 4_565 ?
O3X Gd1 O5X 140.25(11) . . ?
O3X Gd1 O1X 74.95(12) . . ?
O3X Gd1 O1W 142.08(11) . . ?
O3X Gd1 O007 77.18(11) . 4_565 ?
O3X Gd1 O4X 67.22(10) . 3_665 ?
O3X Gd1 O6X 128.05(11) . 3_565 ?
O1W Gd1 O002 70.01(11) . 4_565 ?
O1W Gd1 O1X 129.78(11) . . ?
O1W Gd1 O6X 72.26(11) . 3_565 ?
O007 Gd1 O002 65.97(11) 4_565 4_565 ?
O007 Gd1 O5X 133.98(11) 4_565 . ?
O007 Gd1 O1X 145.81(11) 4_565 . ?
O007 Gd1 O1W 84.37(11) 4_565 . ?
O007 Gd1 O4X 78.67(11) 4_565 3_665 ?
O007 Gd1 O6X 68.55(10) 4_565 3_565 ?
O2X Gd1 O002 68.32(11) . 4_565 ?
O2X Gd1 O5X 81.25(11) . . ?
O2X Gd1 O1X 65.83(11) . . ?
O2X Gd1 O3X 90.99(11) . . ?
O2X Gd1 O1W 78.57(11) . . ?
O2X Gd1 O007 134.26(11) . 4_565 ?
O2X Gd1 O4X 136.88(10) . 3_665 ?
O2X Gd1 O6X 140.75(11) . 3_565 ?
O4X Gd1 O002 130.81(11) 3_665 4_565 ?
O4X Gd1 O5X 92.37(11) 3_665 . ?
O4X Gd1 O1X 72.55(11) 3_665 . ?
O4X Gd1 O1W 140.73(11) 3_665 . ?
O4X Gd1 O6X 68.61(10) 3_665 3_565 ?
O6X Gd1 O002 122.44(10) 3_565 4_565 ?
O6X Gd1 O1X 115.52(11) 3_565 . ?
C1W O002 Gd1 119.8(3) . 4_566 ?
C3W O5X Gd1 120.2(3) . . ?
C1W O1X Gd1 113.0(3) . . ?
C4W O3X Gd1 118.6(3) . . ?
Gd1 O1W H1WA 111.2 . . ?
Gd1 O1W H1WB 110.7 . . ?
H1WA O1W H1WB 107.8 . . ?
C2W O007 Gd1 120.9(3) . 4_566 ?
C2W O2X Gd1 118.7(3) . . ?
C4W O4X Gd1 118.3(3) . 3_665 ?
C3W O6X Gd1 119.9(3) . 3_565 ?
O007 C2W O2X 126.8(4) . . ?
O007 C2W C1W 116.4(4) . . ?
O2X C2W C1W 116.7(4) . . ?
C1 O1 H1 109.5 . . ?
O5X C3W O6X 127.1(4) . . ?
O5X C3W C3W 117.2(5) . 3_565 ?
O6X C3W C3W 115.7(5) . 3_565 ?
O002 C1W C2W 115.9(4) . . ?
O1X C1W O002 127.9(4) . . ?
O1X C1W C2W 116.2(4) . . ?
O3X C4W O4X 126.1(4) . . ?
O3X C4W C4W 117.3(5) . 3_665 ?
O4X C4W C4W 116.6(5) . 3_665 ?
C4 O00G H00G 109.5 . . ?
C2 N1 H1A 107.2 . . ?
C2 N1 C3 111.3(4) . . ?
C3 N1 H1A 107.2 . . ?
C5 N1 H1A 107.2 . . ?
C5 N1 C2 109.4(4) . . ?
C5 N1 C3 114.1(4) . . ?
N1 C2 H2A 109.1 . . ?
N1 C2 H2B 109.1 . . ?
N1 C2 C1 112.7(4) . . ?
H2A C2 H2B 107.8 . . ?
C1 C2 H2A 109.1 . . ?
C1 C2 H2B 109.1 . . ?
N1 C3 H3A 108.2 . . ?
N1 C3 H3B 108.2 . . ?
H3A C3 H3B 107.3 . . ?
C4 C3 N1 116.5(4) . . ?
C4 C3 H3A 108.2 . . ?
C4 C3 H3B 108.2 . . ?
O00G C4 C3 114.1(5) . . ?
O00G C4 H4A 108.7 . . ?
O00G C4 H4B 108.7 . . ?
C3 C4 H4A 108.7 . . ?
C3 C4 H4B 108.7 . . ?
H4A C4 H4B 107.6 . . ?
O1 C1 C2 112.5(4) . . ?
O1 C1 H1B 109.1 . . ?
O1 C1 H1C 109.1 . . ?
C2 C1 H1B 109.1 . . ?
C2 C1 H1C 109.1 . . ?
H1B C1 H1C 107.8 . . ?
N1 C5 C5 111.6(6) . 3_666 ?
N1 C5 H5A 109.3 . . ?
N1 C5 H5B 109.3 . . ?
C5 C5 H5A 109.3 3_666 . ?
C5 C5 H5B 109.3 3_666 . ?
H5A C5 H5B 108.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Gd1 O002 C1W O1X -174.4(4) 4_566 . . . ?
Gd1 O002 C1W C2W 2.3(5) 4_566 . . . ?
Gd1 O5X C3W O6X -172.8(3) . . . . ?
Gd1 O5X C3W C3W 7.0(6) . . . 3_565 ?
Gd1 O1X C1W O002 -153.5(4) . . . . ?
Gd1 O1X C1W C2W 29.9(5) . . . . ?
Gd1 O3X C4W O4X -168.8(3) . . . . ?
Gd1 O3X C4W C4W 11.6(6) . . . 3_665 ?
Gd1 O007 C2W O2X -169.0(4) 4_566 . . . ?
Gd1 O007 C2W C1W 12.0(5) 4_566 . . . ?
Gd1 O2X C2W O007 165.6(4) . . . . ?
Gd1 O2X C2W C1W -15.4(5) . . . . ?
Gd1 O4X C4W O3X -168.7(3) 3_665 . . . ?
Gd1 O4X C4W C4W 11.0(6) 3_665 . . 3_665 ?
Gd1 O6X C3W O5X -173.0(4) 3_565 . . . ?
Gd1 O6X C3W C3W 7.1(6) 3_565 . . 3_565 ?
O007 C2W C1W O002 -9.4(6) . . . . ?
O007 C2W C1W O1X 167.6(4) . . . . ?
O2X C2W C1W O002 171.5(4) . . . . ?
O2X C2W C1W O1X -11.4(6) . . . . ?
N1 C2 C1 O1 -69.5(5) . . . . ?
N1 C3 C4 O00G 79.6(6) . . . . ?
C2 N1 C3 C4 -55.6(6) . . . . ?
C2 N1 C5 C5 -169.1(5) . . . 3_666 ?
C3 N1 C2 C1 -60.5(6) . . . . ?
C3 N1 C5 C5 65.5(7) . . . 3_666 ?
C5 N1 C2 C1 172.5(4) . . . . ?
C5 N1 C3 C4 68.8(6) . . . . ?

_shelx_SHELXL_version_number     23-Oct-2016

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

data_a
_database_code_depnum_ccdc_archive 'CCDC 1508177'
_audit_update_record             
;
2016-11-03 deposited with the CCDC.
2016-11-14 downloaded from the CCDC.
;
_audit_creation_date             2016-10-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H2 O9 Tb, C5 H13 N O2'
_chemical_formula_sum            'C9 H15 N O11 Tb'
_chemical_formula_weight         472.14
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.2803(3)
_cell_length_b                   11.7237(4)
_cell_length_c                   11.4883(4)
_cell_angle_alpha                90
_cell_angle_beta                 104.7650(10)
_cell_angle_gamma                90
_cell_volume                     1338.89(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7986
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.51
_cell_measurement_theta_min      2.53
_shelx_estimated_absorpt_T_max   0.835
_shelx_estimated_absorpt_T_min   0.614
_exptl_absorpt_coefficient_mu    5.345
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6162
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0917 before and 0.0354 after correction. The Ratio of minimum to maximum transmission is 0.8264.
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    2.342
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             916
_exptl_crystal_size_max          0.101
_exptl_crystal_size_mid          0.089
_exptl_crystal_size_min          0.035
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_Laue_measured_fraction_full 0.997
_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       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10003
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         2.526
_diffrn_ambient_temperature      120.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2238
_reflns_number_total             2357
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    ?
_refine_diff_density_max         2.092
_refine_diff_density_min         -0.824
_refine_diff_density_rms         0.119
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2357
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0200
_refine_ls_R_factor_gt           0.0185
_refine_ls_restrained_S_all      1.112
_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)+(0.0204P)²+3.6493P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0451
_refine_ls_wR_factor_ref         0.0456
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2.a Rotating group:
 O00B(H00M,H00N)
2.b Ternary CH refined with riding coordinates:
 N00D(H00D)
2.c Secondary CH2 refined with riding coordinates:
 C00E(H00A,H00B), C00F(H00E,H00F), C00H(H00G,H00H), C00J(H00I,H00J), C00L(H00K,
 H00L)
2.d Idealised tetrahedral OH refined as rotating group:
 O003(H003), O00C(H00C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
Tb01 Tb 0.24702(2) 0.65141(2) -0.01772(2) 0.00407(7) Uani 1 1 d . . . . .
O002 O 0.6615(2) 0.5398(2) -0.0072(2) 0.0086(5) Uani 1 1 d . . . . .
O003 O 0.2179(3) 0.2246(2) 0.5864(3) 0.0235(6) Uani 1 1 d . . . . .
H003 H 0.2442 0.1631 0.5626 0.035 Uiso 1 1 calc GR . . . .
O004 O 0.4862(2) 0.64847(19) 0.0056(2) 0.0095(5) Uani 1 1 d . . . . .
O005 O 0.0832(2) 0.6084(2) 0.0938(2) 0.0102(5) Uani 1 1 d . . . . .
O006 O 0.3055(2) 0.68227(19) 0.3756(2) 0.0075(5) Uani 1 1 d . . . . .
O007 O 0.2631(2) 0.8905(2) 0.2818(2) 0.0090(5) Uani 1 1 d . . . . .
O008 O 0.2664(2) 0.82098(19) 0.1008(2) 0.0088(5) Uani 1 1 d . . . . .
O009 O 0.3487(2) 0.6194(2) 0.2038(2) 0.0100(5) Uani 1 1 d . . . . .
O00A O -0.0797(2) 0.4898(2) 0.1161(2) 0.0089(5) Uani 1 1 d . . . . .
O00B O 0.0449(2) 0.7530(2) -0.1199(2) 0.0113(5) Uani 1 1 d . . . . .
H00M H 0.0564 0.8293 -0.1112 0.017 Uiso 1 1 d GR . . . .
H00N H -0.0252 0.7333 -0.0899 0.017 Uiso 1 1 d GR . . . .
O00C O 0.0213(2) 0.5172(2) 0.3546(2) 0.0127(5) Uani 1 1 d . . . . .
H00C H -0.0141 0.5195 0.2802 0.019 Uiso 1 1 calc GR . . . .
N00D N 0.3147(3) 0.4608(3) 0.4808(3) 0.0148(7) Uani 1 1 d . . . . .
H00D H 0.2847 0.5422 0.4722 0.018 Uiso 1 1 calc R . . . .
C00E C 0.2187(3) 0.3946(3) 0.3824(3) 0.0120(7) Uani 1 1 d . . . . .
H00A H 0.2445 0.3130 0.3894 0.014 Uiso 1 1 calc R . . . .
H00B H 0.2273 0.4222 0.3032 0.014 Uiso 1 1 calc R . . . .
C00F C 0.3083(4) 0.4213(3) 0.6090(4) 0.0225(9) Uani 1 1 d . . . . .
H00E H 0.3752 0.4659 0.6691 0.027 Uiso 1 1 calc R . . . .
H00F H 0.2183 0.4407 0.6195 0.027 Uiso 1 1 calc R . . . .
C00G C 0.5423(3) 0.5547(3) -0.0005(3) 0.0066(7) Uani 1 1 d . . . . .
C00H C 0.3335(4) 0.2974(4) 0.6367(4) 0.0246(9) Uani 1 1 d . . . . .
H00G H 0.4098 0.2722 0.6051 0.030 Uiso 1 1 calc R . . . .
H00H H 0.3601 0.2873 0.7252 0.030 Uiso 1 1 calc R . . . .
C00I C 0.0015(3) 0.5290(3) 0.0606(3) 0.0071(7) Uani 1 1 d . . . . .
C00J C 0.4534(3) 0.4576(3) 0.4596(3) 0.0158(8) Uani 1 1 d . . . . .
H00I H 0.4475 0.4759 0.3743 0.019 Uiso 1 1 calc R . . . .
H00J H 0.4910 0.3798 0.4759 0.019 Uiso 1 1 calc R . . . .
C00K C 0.2768(3) 0.8126(3) 0.2121(3) 0.0065(7) Uani 1 1 d . . . . .
C00L C 0.0733(4) 0.4056(3) 0.3872(3) 0.0143(8) Uani 1 1 d . . . . .
H00K H 0.0181 0.3492 0.3318 0.017 Uiso 1 1 calc R . . . .
H00L H 0.0664 0.3880 0.4697 0.017 Uiso 1 1 calc R . . . .
C00M C 0.3127(3) 0.6928(3) 0.2681(3) 0.0059(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Tb01 O002 2.419(2) 3_665 ?
Tb01 O004 2.405(2) . ?
Tb01 O005 2.415(2) . ?
Tb01 O006 2.458(2) 4_575 ?
Tb01 O007 2.402(2) 4_575 ?
Tb01 O008 2.389(2) . ?
Tb01 O009 2.520(2) . ?
Tb01 O00A 2.446(2) 3_565 ?
Tb01 O00B 2.423(2) . ?
O002 Tb01 2.420(2) 3_665 ?
O002 C00G 1.260(4) . ?
O003 H003 0.8400 . ?
O003 C00H 1.457(5) . ?
O004 C00G 1.252(4) . ?
O005 C00I 1.247(4) . ?
O006 Tb01 2.458(2) 4_576 ?
O006 C00M 1.263(4) . ?
O007 Tb01 2.402(2) 4_576 ?
O007 C00K 1.246(4) . ?
O008 C00K 1.260(4) . ?
O009 C00M 1.250(4) . ?
O00A Tb01 2.446(2) 3_565 ?
O00A C00I 1.259(4) . ?
O00B H00M 0.9042 . ?
O00B H00N 0.9041 . ?
O00C H00C 0.8400 . ?
O00C C00L 1.426(4) . ?
N00D H00D 1.0000 . ?
N00D C00E 1.512(4) . ?
N00D C00F 1.561(5) . ?
N00D C00J 1.506(4) . ?
C00E H00A 0.9900 . ?
C00E H00B 0.9900 . ?
C00E C00L 1.516(5) . ?
C00F H00E 0.9900 . ?
C00F H00F 0.9900 . ?
C00F C00H 1.496(6) . ?
C00G C00G 1.550(6) 3_665 ?
C00H H00G 0.9900 . ?
C00H H00H 0.9900 . ?
C00I C00I 1.543(6) 3_565 ?
C00J C00J 1.522(7) 3_666 ?
C00J H00I 0.9900 . ?
C00J H00J 0.9900 . ?
C00K C00M 1.549(5) . ?
C00L H00K 0.9900 . ?
C00L H00L 0.9900 . ?

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
O002 Tb01 O006 131.06(7) 3_665 4_575 ?
O002 Tb01 O009 72.18(8) 3_665 . ?
O002 Tb01 O00A 68.54(8) 3_665 3_565 ?
O002 Tb01 O00B 140.55(8) 3_665 . ?
O004 Tb01 O002 67.55(7) . 3_665 ?
O004 Tb01 O005 140.30(8) . . ?
O004 Tb01 O006 72.16(8) . 4_575 ?
O004 Tb01 O009 74.72(8) . . ?
O004 Tb01 O00A 128.35(8) . 3_565 ?
O004 Tb01 O00B 141.93(8) . . ?
O005 Tb01 O002 92.66(8) . 3_665 ?
O005 Tb01 O006 136.26(8) . 4_575 ?
O005 Tb01 O009 66.35(8) . . ?
O005 Tb01 O00A 66.44(8) . 3_565 ?
O005 Tb01 O00B 74.45(8) . . ?
O006 Tb01 O009 122.03(8) 4_575 . ?
O007 Tb01 O002 78.71(8) 4_575 3_665 ?
O007 Tb01 O004 77.61(8) 4_575 . ?
O007 Tb01 O005 133.94(8) 4_575 . ?
O007 Tb01 O006 66.35(8) 4_575 4_575 ?
O007 Tb01 O009 145.65(8) 4_575 . ?
O007 Tb01 O00A 68.34(7) 4_575 3_565 ?
O007 Tb01 O00B 84.04(8) 4_575 . ?
O008 Tb01 O002 136.91(8) . 3_665 ?
O008 Tb01 O004 90.81(8) . . ?
O008 Tb01 O005 80.76(8) . . ?
O008 Tb01 O006 68.18(8) . 4_575 ?
O008 Tb01 O007 134.47(8) . 4_575 ?
O008 Tb01 O009 66.17(8) . . ?
O008 Tb01 O00A 140.61(8) . 3_565 ?
O008 Tb01 O00B 78.67(8) . . ?
O00A Tb01 O006 122.63(8) 3_565 4_575 ?
O00A Tb01 O009 115.29(8) 3_565 . ?
O00B Tb01 O006 69.95(8) . 4_575 ?
O00B Tb01 O009 130.24(8) . . ?
O00B Tb01 O00A 72.16(8) . 3_565 ?
C00G O002 Tb01 118.4(2) . 3_665 ?
C00H O003 H003 109.5 . . ?
C00G O004 Tb01 118.6(2) . . ?
C00I O005 Tb01 120.0(2) . . ?
C00M O006 Tb01 119.5(2) . 4_576 ?
C00K O007 Tb01 120.8(2) . 4_576 ?
C00K O008 Tb01 119.1(2) . . ?
C00M O009 Tb01 112.6(2) . . ?
C00I O00A Tb01 119.5(2) . 3_565 ?
Tb01 O00B H00M 111.2 . . ?
Tb01 O00B H00N 111.0 . . ?
H00M O00B H00N 107.7 . . ?
C00L O00C H00C 109.5 . . ?
C00E N00D H00D 106.8 . . ?
C00E N00D C00F 112.1(3) . . ?
C00F N00D H00D 106.8 . . ?
C00J N00D H00D 106.8 . . ?
C00J N00D C00E 109.3(3) . . ?
C00J N00D C00F 114.5(3) . . ?
N00D C00E H00A 109.0 . . ?
N00D C00E H00B 109.0 . . ?
N00D C00E C00L 113.0(3) . . ?
H00A C00E H00B 107.8 . . ?
C00L C00E H00A 109.0 . . ?
C00L C00E H00B 109.0 . . ?
N00D C00F H00E 108.2 . . ?
N00D C00F H00F 108.2 . . ?
H00E C00F H00F 107.4 . . ?
C00H C00F N00D 116.2(3) . . ?
C00H C00F H00E 108.2 . . ?
C00H C00F H00F 108.2 . . ?
O002 C00G C00G 116.3(4) . 3_665 ?
O004 C00G O002 126.4(3) . . ?
O004 C00G C00G 117.3(3) . 3_665 ?
O003 C00H C00F 113.9(3) . . ?
O003 C00H H00G 108.8 . . ?
O003 C00H H00H 108.8 . . ?
C00F C00H H00G 108.8 . . ?
C00F C00H H00H 108.8 . . ?
H00G C00H H00H 107.7 . . ?
O005 C00I O00A 126.9(3) . . ?
O005 C00I C00I 117.5(3) . 3_565 ?
O00A C00I C00I 115.6(4) . 3_565 ?
N00D C00J C00J 111.1(4) . 3_666 ?
N00D C00J H00I 109.4 . . ?
N00D C00J H00J 109.4 . . ?
C00J C00J H00I 109.4 3_666 . ?
C00J C00J H00J 109.4 3_666 . ?
H00I C00J H00J 108.0 . . ?
O007 C00K O008 126.9(3) . . ?
O007 C00K C00M 116.9(3) . . ?
O008 C00K C00M 116.2(3) . . ?
O00C C00L C00E 112.1(3) . . ?
O00C C00L H00K 109.2 . . ?
O00C C00L H00L 109.2 . . ?
C00E C00L H00K 109.2 . . ?
C00E C00L H00L 109.2 . . ?
H00K C00L H00L 107.9 . . ?
O006 C00M C00K 115.3(3) . . ?
O009 C00M O006 127.6(3) . . ?
O009 C00M C00K 117.0(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Tb01 O002 C00G O004 169.3(3) 3_665 . . . ?
Tb01 O002 C00G C00G -10.5(4) 3_665 . . 3_665 ?
Tb01 O004 C00G O002 169.3(2) . . . . ?
Tb01 O004 C00G C00G -10.8(4) . . . 3_665 ?
Tb01 O005 C00I O00A 172.3(3) . . . . ?
Tb01 O005 C00I C00I -7.2(5) . . . 3_565 ?
Tb01 O006 C00M O009 175.3(3) 4_576 . . . ?
Tb01 O006 C00M C00K -2.4(3) 4_576 . . . ?
Tb01 O007 C00K O008 168.6(3) 4_576 . . . ?
Tb01 O007 C00K C00M -12.4(4) 4_576 . . . ?
Tb01 O008 C00K O007 -165.8(3) . . . . ?
Tb01 O008 C00K C00M 15.2(4) . . . . ?
Tb01 O009 C00M O006 153.7(3) . . . . ?
Tb01 O009 C00M C00K -28.6(3) . . . . ?
Tb01 O00A C00I O005 172.8(3) 3_565 . . . ?
Tb01 O00A C00I C00I -7.8(5) 3_565 . . 3_565 ?
O007 C00K C00M O006 9.8(4) . . . . ?
O007 C00K C00M O009 -168.3(3) . . . . ?
O008 C00K C00M O006 -171.1(3) . . . . ?
O008 C00K C00M O009 10.8(4) . . . . ?
N00D C00E C00L O00C 70.0(4) . . . . ?
N00D C00F C00H O003 -79.2(4) . . . . ?
C00E N00D C00F C00H 56.2(4) . . . . ?
C00E N00D C00J C00J 168.3(4) . . . 3_666 ?
C00F N00D C00E C00L 59.2(4) . . . . ?
C00F N00D C00J C00J -65.0(5) . . . 3_666 ?
C00J N00D C00E C00L -172.7(3) . . . . ?
C00J N00D C00F C00H -69.0(4) . . . . ?

_shelx_SHELXL_version_number     27-10-2016

_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_a
_database_code_depnum_ccdc_archive 'CCDC 1508178'
_audit_update_record             
;
2016-11-03 deposited with the CCDC.
2016-11-14 downloaded from the CCDC.
;
_audit_creation_date             2016-10-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H2 Dy O9, 0.5(C10 H26 N2 O4) '
_chemical_formula_sum            'C9 H15 Dy N O11'
_chemical_formula_weight         475.72
_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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.2355(4)
_cell_length_b                   11.7090(4)
_cell_length_c                   11.4476(4)
_cell_angle_alpha                90
_cell_angle_beta                 104.3930(10)
_cell_angle_gamma                90
_cell_volume                     1328.90(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9988
_cell_measurement_temperature    137(2)
_cell_measurement_theta_max      27.52
_cell_measurement_theta_min      3.48
_shelx_estimated_absorpt_T_max   0.826
_shelx_estimated_absorpt_T_min   0.568
_exptl_absorpt_coefficient_mu    5.686
_exptl_absorpt_correction_T_max  0.482
_exptl_absorpt_correction_T_min  0.298
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.378
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.112
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.035
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0156
_diffrn_reflns_av_unetI/netI     0.0099
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            16829
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.028
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         2.957
_diffrn_ambient_temperature      136.99
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2283
_reflns_number_total             2337
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    ?
_refine_diff_density_max         1.926
_refine_diff_density_min         -0.731
_refine_diff_density_rms         0.103
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2337
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0161
_refine_ls_R_factor_gt           0.0156
_refine_ls_restrained_S_all      1.120
_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)+(0.0202P)²+3.1321P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0398
_refine_ls_wR_factor_ref         0.0400
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2.a Rotating group:
 O1W(H1WA,H1WB)
2.b Ternary CH refined with riding coordinates:
 N1(H1)
2.c Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C2(H2A,H2B), C5(H5A,H5B), C3(H3A,H3B), C1(H1B,H1C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1A), O2(H2)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
Dy1 Dy 0.75286(2) 0.34883(2) 1.01832(2) 0.00490(6) Uani 1 1 d . . . . .
N1 N 0.6858(2) 0.5397(2) 0.5193(2) 0.0147(5) Uani 1 1 d . . . . .
H1 H 0.7160 0.4583 0.5278 0.018 Uiso 1 1 calc R . . . .
O6X O 0.33784(19) 0.46022(16) 1.00629(18) 0.0092(4) Uani 1 1 d . . . . .
O1 O 0.9784(2) 0.48258(17) 0.64510(19) 0.0140(4) Uani 1 1 d . . . . .
H1A H 1.0128 0.4795 0.7197 0.021 Uiso 1 1 calc GR . . . .
C4 C 0.6935(3) 0.5786(3) 0.3922(3) 0.0211(7) Uani 1 1 d . . . . .
H4A H 0.7844 0.5596 0.3822 0.025 Uiso 1 1 calc R . . . .
H4B H 0.6275 0.5333 0.3320 0.025 Uiso 1 1 calc R . . . .
O3X O 0.7371(2) 0.10993(16) 0.71844(17) 0.0102(4) Uani 1 1 d . . . . .
O8X O 1.08027(19) 0.51017(17) 0.88370(17) 0.0100(4) Uani 1 1 d . . . . .
O7X O 0.9165(2) 0.39208(17) 0.90637(18) 0.0119(4) Uani 1 1 d . . . . .
O1X O 0.6521(2) 0.38137(17) 0.79701(18) 0.0112(4) Uani 1 1 d . . . . .
C2 C 0.7811(3) 0.6054(3) 0.6177(3) 0.0135(6) Uani 1 1 d . . . . .
H2A H 0.7718 0.5776 0.6969 0.016 Uiso 1 1 calc R . . . .
H2B H 0.7554 0.6871 0.6110 0.016 Uiso 1 1 calc R . . . .
O5X O 0.5144(2) 0.35158(15) 0.9951(2) 0.0102(4) Uani 1 1 d . . . . .
O2X O 0.7346(2) 0.17970(16) 0.90030(18) 0.0096(4) Uani 1 1 d . . . . .
O2 O 0.7827(2) 0.7752(2) 0.4138(2) 0.0241(5) Uani 1 1 d . . . . .
H2 H 0.7565 0.8349 0.4417 0.036 Uiso 1 1 calc GR . . . .
O1W O 0.95354(19) 0.24729(17) 1.11966(18) 0.0119(4) Uani 1 1 d . . . . .
H1WA H 1.0238 0.2669 1.0898 0.018 Uiso 1 1 d GR . . . .
H1WB H 0.9414 0.1714 1.1106 0.018 Uiso 1 1 d GR . . . .
O4X O 0.69386(19) 0.31793(16) 0.62433(17) 0.0081(4) Uani 1 1 d . . . . .
C5 C 0.6675(3) 0.7030(3) 0.3628(3) 0.0225(7) Uani 1 1 d . . . . .
H5A H 0.6424 0.7125 0.2741 0.027 Uiso 1 1 calc R . . . .
H5B H 0.5900 0.7284 0.3937 0.027 Uiso 1 1 calc R . . . .
C3 C 0.5466(3) 0.5425(3) 0.5407(3) 0.0163(6) Uani 1 1 d . . . . .
H3A H 0.5088 0.6204 0.5247 0.020 Uiso 1 1 calc R . . . .
H3B H 0.5521 0.5238 0.6261 0.020 Uiso 1 1 calc R . . . .
C1 C 0.9267(3) 0.5947(3) 0.6133(3) 0.0153(6) Uani 1 1 d . . . . .
H1B H 0.9346 0.6130 0.5309 0.018 Uiso 1 1 calc R . . . .
H1C H 0.9816 0.6507 0.6695 0.018 Uiso 1 1 calc R . . . .
C3X C 0.4576(3) 0.4451(2) 1.0004(2) 0.0080(6) Uani 1 1 d . . . . .
C4X C 0.9988(3) 0.4710(2) 0.9391(2) 0.0078(6) Uani 1 1 d . . . . .
C2X C 0.7234(3) 0.1884(2) 0.7886(2) 0.0074(5) Uani 1 1 d . . . . .
C1X C 0.6871(3) 0.3075(2) 0.7320(2) 0.0074(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
Dy1 O6X 2.4105(19) 3_667 ?
Dy1 O3X 2.3857(19) 4_566 ?
Dy1 O8X 2.4390(19) 3_767 ?
Dy1 O7X 2.4027(19) . ?
Dy1 O1X 2.516(2) . ?
Dy1 O5X 2.389(2) . ?
Dy1 O2X 2.3783(19) . ?
Dy1 O1W 2.4070(19) . ?
Dy1 O4X 2.4525(19) 4_566 ?
N1 H1 1.0000 . ?
N1 C4 1.545(4) . ?
N1 C2 1.506(4) . ?
N1 C3 1.505(4) . ?
O6X Dy1 2.4105(19) 3_667 ?
O6X C3X 1.257(3) . ?
O1 H1A 0.8400 . ?
O1 C1 1.428(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.503(5) . ?
O3X Dy1 2.3857(19) 4_565 ?
O3X C2X 1.250(3) . ?
O8X Dy1 2.4390(19) 3_767 ?
O8X C4X 1.254(3) . ?
O7X C4X 1.244(3) . ?
O1X C1X 1.249(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C1 1.509(4) . ?
O5X C3X 1.248(3) . ?
O2X C2X 1.260(4) . ?
O2 H2 0.8400 . ?
O2 C5 1.451(4) . ?
O1W H1WA 0.8997 . ?
O1W H1WB 0.8996 . ?
O4X Dy1 2.4525(19) 4_565 ?
O4X C1X 1.258(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C3 C3 1.525(6) 3_666 ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C1 H1B 0.9900 . ?
C1 H1C 0.9900 . ?
C3X C3X 1.552(5) 3_667 ?
C4X C4X 1.545(5) 3_767 ?
C2X C1X 1.544(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O6X Dy1 O8X 68.36(6) 3_667 3_767 ?
O6X Dy1 O1X 72.08(6) 3_667 . ?
O6X Dy1 O4X 131.40(6) 3_667 4_566 ?
O3X Dy1 O6X 78.95(7) 4_566 3_667 ?
O3X Dy1 O8X 68.17(6) 4_566 3_767 ?
O3X Dy1 O7X 133.80(7) 4_566 . ?
O3X Dy1 O1X 145.87(7) 4_566 . ?
O3X Dy1 O5X 78.04(7) 4_566 . ?
O3X Dy1 O1W 83.71(7) 4_566 . ?
O3X Dy1 O4X 66.56(6) 4_566 4_566 ?
O8X Dy1 O1X 115.19(7) 3_767 . ?
O8X Dy1 O4X 122.81(6) 3_767 4_566 ?
O7X Dy1 O6X 92.38(7) . 3_667 ?
O7X Dy1 O8X 66.50(7) . 3_767 ?
O7X Dy1 O1X 66.21(7) . . ?
O7X Dy1 O1W 74.73(7) . . ?
O7X Dy1 O4X 136.21(7) . 4_566 ?
O5X Dy1 O6X 67.75(6) . 3_667 ?
O5X Dy1 O8X 128.41(6) . 3_767 ?
O5X Dy1 O7X 140.05(7) . . ?
O5X Dy1 O1X 74.59(7) . . ?
O5X Dy1 O1W 141.82(7) . . ?
O5X Dy1 O4X 72.26(6) . 4_566 ?
O2X Dy1 O6X 137.09(7) . 3_667 ?
O2X Dy1 O3X 134.39(7) . 4_566 ?
O2X Dy1 O8X 140.54(7) . 3_767 ?
O2X Dy1 O7X 80.75(7) . . ?
O2X Dy1 O1X 66.38(7) . . ?
O2X Dy1 O5X 90.82(7) . . ?
O2X Dy1 O1W 78.44(7) . . ?
O2X Dy1 O4X 67.91(7) . 4_566 ?
O1W Dy1 O6X 140.55(7) . 3_667 ?
O1W Dy1 O8X 72.34(7) . 3_767 ?
O1W Dy1 O1X 130.34(7) . . ?
O1W Dy1 O4X 69.75(7) . 4_566 ?
O4X Dy1 O1X 121.95(7) 4_566 . ?
C4 N1 H1 106.7 . . ?
C2 N1 H1 106.7 . . ?
C2 N1 C4 112.3(2) . . ?
C3 N1 H1 106.7 . . ?
C3 N1 C4 114.8(2) . . ?
C3 N1 C2 109.3(2) . . ?
C3X O6X Dy1 118.48(17) . 3_667 ?
C1 O1 H1A 109.5 . . ?
N1 C4 H4A 108.1 . . ?
N1 C4 H4B 108.1 . . ?
H4A C4 H4B 107.3 . . ?
C5 C4 N1 116.6(3) . . ?
C5 C4 H4A 108.1 . . ?
C5 C4 H4B 108.1 . . ?
C2X O3X Dy1 120.85(18) . 4_565 ?
C4X O8X Dy1 119.52(17) . 3_767 ?
C4X O7X Dy1 120.36(17) . . ?
C1X O1X Dy1 112.85(17) . . ?
N1 C2 H2A 108.9 . . ?
N1 C2 H2B 108.9 . . ?
N1 C2 C1 113.2(2) . . ?
H2A C2 H2B 107.7 . . ?
C1 C2 H2A 108.9 . . ?
C1 C2 H2B 108.9 . . ?
C3X O5X Dy1 118.77(17) . . ?
C2X O2X Dy1 118.97(17) . . ?
C5 O2 H2 109.5 . . ?
Dy1 O1W H1WA 111.0 . . ?
Dy1 O1W H1WB 110.8 . . ?
H1WA O1W H1WB 107.9 . . ?
C1X O4X Dy1 119.24(17) . 4_565 ?
C4 C5 H5A 108.9 . . ?
C4 C5 H5B 108.9 . . ?
O2 C5 C4 113.2(3) . . ?
O2 C5 H5A 108.9 . . ?
O2 C5 H5B 108.9 . . ?
H5A C5 H5B 107.8 . . ?
N1 C3 C3 111.1(3) . 3_666 ?
N1 C3 H3A 109.4 . . ?
N1 C3 H3B 109.4 . . ?
C3 C3 H3A 109.4 3_666 . ?
C3 C3 H3B 109.4 3_666 . ?
H3A C3 H3B 108.0 . . ?
O1 C1 C2 112.0(2) . . ?
O1 C1 H1B 109.2 . . ?
O1 C1 H1C 109.2 . . ?
C2 C1 H1B 109.2 . . ?
C2 C1 H1C 109.2 . . ?
H1B C1 H1C 107.9 . . ?
O6X C3X C3X 115.9(3) . 3_667 ?
O5X C3X O6X 126.7(3) . . ?
O5X C3X C3X 117.3(3) . 3_667 ?
O8X C4X C4X 115.6(3) . 3_767 ?
O7X C4X O8X 127.2(3) . . ?
O7X C4X C4X 117.1(3) . 3_767 ?
O3X C2X O2X 126.6(3) . . ?
O3X C2X C1X 116.7(2) . . ?
O2X C2X C1X 116.7(2) . . ?
O1X C1X O4X 127.6(3) . . ?
O1X C1X C2X 116.8(2) . . ?
O4X C1X C2X 115.6(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
Dy1 O6X C3X O5X -169.8(2) 3_667 . . . ?
Dy1 O6X C3X C3X 10.1(4) 3_667 . . 3_667 ?
Dy1 O3X C2X O2X -168.3(2) 4_565 . . . ?
Dy1 O3X C2X C1X 12.7(3) 4_565 . . . ?
Dy1 O8X C4X O7X -173.1(2) 3_767 . . . ?
Dy1 O8X C4X C4X 7.6(4) 3_767 . . 3_767 ?
Dy1 O7X C4X O8X -172.4(2) . . . . ?
Dy1 O7X C4X C4X 6.8(4) . . . 3_767 ?
Dy1 O1X C1X O4X -154.0(2) . . . . ?
Dy1 O1X C1X C2X 27.5(3) . . . . ?
Dy1 O5X C3X O6X -169.8(2) . . . . ?
Dy1 O5X C3X C3X 10.3(4) . . . 3_667 ?
Dy1 O2X C2X O3X 166.2(2) . . . . ?
Dy1 O2X C2X C1X -14.8(3) . . . . ?
Dy1 O4X C1X O1X -176.1(2) 4_565 . . . ?
Dy1 O4X C1X C2X 2.4(3) 4_565 . . . ?
N1 C4 C5 O2 79.0(3) . . . . ?
N1 C2 C1 O1 -69.7(3) . . . . ?
C4 N1 C2 C1 -59.0(3) . . . . ?
C4 N1 C3 C3 64.6(4) . . . 3_666 ?
O3X C2X C1X O1X 168.8(2) . . . . ?
O3X C2X C1X O4X -9.9(4) . . . . ?
C2 N1 C4 C5 -56.9(3) . . . . ?
C2 N1 C3 C3 -168.2(3) . . . 3_666 ?
O2X C2X C1X O1X -10.3(4) . . . . ?
O2X C2X C1X O4X 171.0(2) . . . . ?
C3 N1 C4 C5 68.7(3) . . . . ?
C3 N1 C2 C1 172.5(2) . . . . ?

_shelx_SHELXL_version_number     2014/7

_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_a
_database_code_depnum_ccdc_archive 'CCDC 1508179'
_audit_update_record             
;
2016-11-03 deposited with the CCDC.
2016-11-14 downloaded from the CCDC.
;
_audit_creation_date             2016-10-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H2 Ho O9, 0.5(C10 H26 N2 O4)'
_chemical_formula_sum            'C9 H15 Ho N O11'
_chemical_formula_weight         478.15
_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'
Ho Ho -0.2175 4.6783 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.2074(4)
_cell_length_b                   11.6791(4)
_cell_length_c                   11.4238(5)
_cell_angle_alpha                90
_cell_angle_beta                 104.2460(10)
_cell_angle_gamma                90
_cell_volume                     1319.99(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8385
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.52
_cell_measurement_theta_min      2.53
_shelx_estimated_absorpt_T_max   0.798
_shelx_estimated_absorpt_T_min   0.627
_exptl_absorpt_coefficient_mu    6.058
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6244
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0778 before and 0.0416 after correction. 
The Ratio of minimum to maximum transmission is 0.8374.
 The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            pink
_exptl_crystal_colour_primary    pink
_exptl_crystal_density_diffrn    2.406
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             924
_exptl_crystal_size_max          0.085
_exptl_crystal_size_mid          0.046
_exptl_crystal_size_min          0.039
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_unetI/netI     0.0254
_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       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15157
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.544
_diffrn_reflns_theta_min         2.535
_diffrn_ambient_temperature      120.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2708
_reflns_number_total             3033
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    ?
_refine_diff_density_max         2.470
_refine_diff_density_min         -0.828
_refine_diff_density_rms         0.133
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         3033
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0271
_refine_ls_R_factor_gt           0.0210
_refine_ls_restrained_S_all      1.080
_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)+(0.0168P)²+3.1448P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0433
_refine_ls_wR_factor_ref         0.0447
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Rotating group:
 O1W(H1WA)
2.b Ternary CH refined with riding coordinates:
 N1(H1)
2.c Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4A,H4B), C3(H3A,H3B), C5(H5A,H5B), C1(H1B,H1C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2), O1(H1A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
Ho1 Ho 0.74716(2) 0.65101(2) 0.98112(2) 0.00457(5) Uani 1 1 d . . . . .
O2X O 0.8065(2) 0.81813(18) 0.8754(2) 0.0079(5) Uani 1 1 d . . . . .
O1X O 0.7632(2) 0.61000(19) 0.7812(2) 0.0093(5) Uani 1 1 d . . . . .
O4X O 0.7646(2) 0.68010(18) 0.5986(2) 0.0093(5) Uani 1 1 d . . . . .
O3X O 0.8483(2) 0.88206(19) 0.7020(2) 0.0094(5) Uani 1 1 d . . . . .
O8X O 0.4160(2) 0.3917(2) 0.9064(2) 0.0110(5) Uani 1 1 d . . . . .
O1W O 0.5481(2) 0.7525(2) 0.8798(2) 0.0114(5) Uani 1 1 d . . . . .
H1WA H 0.4792 0.7307 0.9082 0.017 Uiso 1 1 d GR . . . .
O6X O 1.1629(2) 0.53948(18) 0.9947(2) 0.0085(4) Uani 1 1 d . . . . .
O5X O 0.9852(2) 0.64870(18) 1.0040(2) 0.0094(4) Uani 1 1 d . . . . .
O2 O 0.4783(2) 0.48271(19) 0.6447(2) 0.0126(5) Uani 1 1 d . . . . .
H2 H 0.5126 0.4793 0.7194 0.019 Uiso 1 1 calc GR . . . .
O7X O 0.5806(2) 0.50990(19) 0.8835(2) 0.0083(5) Uani 1 1 d . . . . .
C1X C 0.7762(3) 0.6888(3) 0.7109(3) 0.0072(6) Uani 1 1 d . . . . .
C2X C 0.8132(3) 0.8075(3) 0.7669(3) 0.0063(6) Uani 1 1 d . . . . .
N1 N 0.1861(3) 0.5398(2) 0.5196(3) 0.0139(6) Uani 1 1 d . . . . .
H1 H 0.2164 0.4582 0.5288 0.017 Uiso 1 1 calc R . . . .
O1 O 0.2837(2) 0.7763(2) 0.4123(3) 0.0226(6) Uani 1 1 d . . . . .
H1A H 0.2570 0.8363 0.4398 0.034 Uiso 1 1 calc GR . . . .
C4X C 0.4986(3) 0.4711(3) 0.9391(3) 0.0077(6) Uani 1 1 d . . . . .
C2 C 0.1941(4) 0.5785(3) 0.3905(4) 0.0220(8) Uani 1 1 d . . . . .
H2A H 0.2850 0.5591 0.3802 0.026 Uiso 1 1 calc R . . . .
H2B H 0.1276 0.5334 0.3305 0.026 Uiso 1 1 calc R . . . .
C4 C 0.2813(3) 0.6067(3) 0.6186(3) 0.0124(7) Uani 1 1 d . . . . .
H4A H 0.2555 0.6886 0.6113 0.015 Uiso 1 1 calc R . . . .
H4B H 0.2718 0.5792 0.6980 0.015 Uiso 1 1 calc R . . . .
C3X C 1.0427(3) 0.5548(3) 0.9997(3) 0.0071(6) Uani 1 1 d . . . . .
C3 C 0.0461(3) 0.5431(3) 0.5408(3) 0.0147(7) Uani 1 1 d . . . . .
H3A H 0.0081 0.6211 0.5239 0.018 Uiso 1 1 calc R . . . .
H3B H 0.0510 0.5250 0.6264 0.018 Uiso 1 1 calc R . . . .
C5 C 0.4272(3) 0.5952(3) 0.6134(3) 0.0135(7) Uani 1 1 d . . . . .
H5A H 0.4349 0.6135 0.5308 0.016 Uiso 1 1 calc R . . . .
H5B H 0.4827 0.6510 0.6695 0.016 Uiso 1 1 calc R . . . .
C1 C 0.1686(4) 0.7034(3) 0.3617(4) 0.0224(8) Uani 1 1 d . . . . .
H1B H 0.1434 0.7131 0.2729 0.027 Uiso 1 1 calc R . . . .
H1C H 0.0910 0.7287 0.3928 0.027 Uiso 1 1 calc R . . . .
H1WB H 0.554(5) 0.823(4) 0.877(5) 0.045(16) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ho1 O2X 2.448(2) . ?
Ho1 O1X 2.378(2) . ?
Ho1 O4X 2.367(2) 4_576 ?
Ho1 O3X 2.509(2) 4_576 ?
Ho1 O8X 2.394(2) 3_667 ?
Ho1 O1W 2.390(2) . ?
Ho1 O6X 2.397(2) 3_767 ?
Ho1 O5X 2.379(2) . ?
Ho1 O7X 2.433(2) . ?
O2X C2X 1.264(4) . ?
O1X C1X 1.249(4) . ?
O4X Ho1 2.367(2) 4_575 ?
O4X C1X 1.263(4) . ?
O3X Ho1 2.509(2) 4_575 ?
O3X C2X 1.252(4) . ?
O8X Ho1 2.394(2) 3_667 ?
O8X C4X 1.247(4) . ?
O1W H1WA 0.8819 . ?
O1W H1WB 0.83(5) . ?
O6X Ho1 2.397(2) 3_767 ?
O6X C3X 1.254(4) . ?
O5X C3X 1.251(4) . ?
O2 H2 0.8400 . ?
O2 C5 1.426(4) . ?
O7X C4X 1.254(4) . ?
C1X C2X 1.536(4) . ?
N1 H1 1.0000 . ?
N1 C2 1.564(5) . ?
N1 C4 1.514(4) . ?
N1 C3 1.507(4) . ?
O1 H1A 0.8400 . ?
O1 C1 1.451(5) . ?
C4X C4X 1.539(6) 3_667 ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C1 1.503(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.510(5) . ?
C3X C3X 1.549(6) 3_767 ?
C3 C3 1.529(7) 3_566 ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C1 H1B 0.9900 . ?
C1 H1C 0.9900 . ?

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
O2X Ho1 O3X 121.87(7) . 4_576 ?
O1X Ho1 O2X 66.62(7) . . ?
O1X Ho1 O3X 145.69(8) . 4_576 ?
O1X Ho1 O8X 134.03(8) . 3_667 ?
O1X Ho1 O1W 83.46(8) . . ?
O1X Ho1 O6X 78.97(8) . 3_767 ?
O1X Ho1 O5X 78.09(8) . . ?
O1X Ho1 O7X 68.19(7) . . ?
O4X Ho1 O2X 67.79(8) 4_576 . ?
O4X Ho1 O1X 134.32(8) 4_576 . ?
O4X Ho1 O3X 66.64(7) 4_576 4_576 ?
O4X Ho1 O8X 80.48(8) 4_576 3_667 ?
O4X Ho1 O1W 78.33(8) 4_576 . ?
O4X Ho1 O6X 137.29(8) 4_576 3_767 ?
O4X Ho1 O5X 90.85(8) 4_576 . ?
O4X Ho1 O7X 140.44(8) 4_576 . ?
O8X Ho1 O2X 136.09(8) 3_667 . ?
O8X Ho1 O3X 66.19(8) 3_667 4_576 ?
O8X Ho1 O6X 92.42(8) 3_667 3_767 ?
O8X Ho1 O7X 66.72(8) 3_667 . ?
O1W Ho1 O2X 69.52(8) . . ?
O1W Ho1 O3X 130.78(8) . 4_576 ?
O1W Ho1 O8X 75.08(8) . 3_667 ?
O1W Ho1 O6X 140.52(8) . 3_767 ?
O1W Ho1 O7X 72.48(8) . . ?
O6X Ho1 O2X 131.49(7) 3_767 . ?
O6X Ho1 O3X 71.96(7) 3_767 4_576 ?
O6X Ho1 O7X 68.20(7) 3_767 . ?
O5X Ho1 O2X 72.14(7) . . ?
O5X Ho1 O3X 74.43(8) . 4_576 ?
O5X Ho1 O8X 139.94(8) . 3_667 ?
O5X Ho1 O1W 141.47(8) . . ?
O5X Ho1 O6X 67.96(7) . 3_767 ?
O5X Ho1 O7X 128.48(7) . . ?
O7X Ho1 O2X 122.94(7) . . ?
O7X Ho1 O3X 115.14(7) . 4_576 ?
C2X O2X Ho1 119.02(19) . . ?
C1X O1X Ho1 120.8(2) . . ?
C1X O4X Ho1 118.96(19) . 4_575 ?
C2X O3X Ho1 112.46(19) . 4_575 ?
C4X O8X Ho1 120.1(2) . 3_667 ?
Ho1 O1W H1WA 109.8 . . ?
Ho1 O1W H1WB 117(4) . . ?
H1WA O1W H1WB 111.9 . . ?
C3X O6X Ho1 118.6(2) . 3_767 ?
C3X O5X Ho1 118.85(19) . . ?
C5 O2 H2 109.5 . . ?
C4X O7X Ho1 119.4(2) . . ?
O1X C1X O4X 126.6(3) . . ?
O1X C1X C2X 116.8(3) . . ?
O4X C1X C2X 116.6(3) . . ?
O2X C2X C1X 115.5(3) . . ?
O3X C2X O2X 127.3(3) . . ?
O3X C2X C1X 117.2(3) . . ?
C2 N1 H1 106.8 . . ?
C4 N1 H1 106.8 . . ?
C4 N1 C2 112.5(3) . . ?
C3 N1 H1 106.8 . . ?
C3 N1 C2 114.5(3) . . ?
C3 N1 C4 109.1(3) . . ?
C1 O1 H1A 109.5 . . ?
O8X C4X O7X 127.0(3) . . ?
O8X C4X C4X 117.2(3) . 3_667 ?
O7X C4X C4X 115.7(3) . 3_667 ?
N1 C2 H2A 108.3 . . ?
N1 C2 H2B 108.3 . . ?
H2A C2 H2B 107.4 . . ?
C1 C2 N1 116.1(3) . . ?
C1 C2 H2A 108.3 . . ?
C1 C2 H2B 108.3 . . ?
N1 C4 H4A 109.1 . . ?
N1 C4 H4B 109.1 . . ?
H4A C4 H4B 107.8 . . ?
C5 C4 N1 112.5(3) . . ?
C5 C4 H4A 109.1 . . ?
C5 C4 H4B 109.1 . . ?
O6X C3X C3X 116.1(3) . 3_767 ?
O5X C3X O6X 126.9(3) . . ?
O5X C3X C3X 117.0(3) . 3_767 ?
N1 C3 C3 110.6(4) . 3_566 ?
N1 C3 H3A 109.5 . . ?
N1 C3 H3B 109.5 . . ?
C3 C3 H3A 109.5 3_566 . ?
C3 C3 H3B 109.5 3_566 . ?
H3A C3 H3B 108.1 . . ?
O2 C5 C4 112.1(3) . . ?
O2 C5 H5A 109.2 . . ?
O2 C5 H5B 109.2 . . ?
C4 C5 H5A 109.2 . . ?
C4 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
O1 C1 C2 113.8(3) . . ?
O1 C1 H1B 108.8 . . ?
O1 C1 H1C 108.8 . . ?
C2 C1 H1B 108.8 . . ?
C2 C1 H1C 108.8 . . ?
H1B C1 H1C 107.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Ho1 O2X C2X O3X -176.2(2) . . . . ?
Ho1 O2X C2X C1X 2.6(3) . . . . ?
Ho1 O1X C1X O4X -168.1(2) . . . . ?
Ho1 O1X C1X C2X 13.4(3) . . . . ?
Ho1 O4X C1X O1X 166.8(2) 4_575 . . . ?
Ho1 O4X C1X C2X -14.8(3) 4_575 . . . ?
Ho1 O3X C2X O2X -154.1(3) 4_575 . . . ?
Ho1 O3X C2X C1X 27.1(3) 4_575 . . . ?
Ho1 O8X C4X O7X -172.8(2) 3_667 . . . ?
Ho1 O8X C4X C4X 7.1(4) 3_667 . . 3_667 ?
Ho1 O6X C3X O5X 170.5(2) 3_767 . . . ?
Ho1 O6X C3X C3X -9.7(4) 3_767 . . 3_767 ?
Ho1 O5X C3X O6X 170.3(2) . . . . ?
Ho1 O5X C3X C3X -9.5(4) . . . 3_767 ?
Ho1 O7X C4X O8X -173.0(2) . . . . ?
Ho1 O7X C4X C4X 7.0(4) . . . 3_667 ?
O1X C1X C2X O2X -10.5(4) . . . . ?
O1X C1X C2X O3X 168.5(3) . . . . ?
O4X C1X C2X O2X 170.9(3) . . . . ?
O4X C1X C2X O3X -10.2(4) . . . . ?
N1 C2 C1 O1 78.9(4) . . . . ?
N1 C4 C5 O2 -69.3(4) . . . . ?
C2 N1 C4 C5 -59.1(4) . . . . ?
C2 N1 C3 C3 64.8(4) . . . 3_566 ?
C4 N1 C2 C1 -56.2(4) . . . . ?
C4 N1 C3 C3 -168.2(3) . . . 3_566 ?
C3 N1 C2 C1 69.0(4) . . . . ?
C3 N1 C4 C5 172.6(3) . . . . ?

_shelx_SHELXL_version_number     23-Oct-2016

