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

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

data_mb3
_database_code_depnum_ccdc_archive 'CCDC 1537043'
_audit_update_record             
;
2017-03-09 deposited with the CCDC.
2017-04-11 downloaded from the CCDC.
;
_audit_creation_date             2017-02-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H15 N O8 Yb'
_chemical_formula_sum            'C15 H15 N O8 Yb'
_chemical_formula_weight         510.32
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 N2 O2 Yb'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Yb Yb -0.3850 5.5486 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   8.5054(2)
_cell_length_b                   10.2435(2)
_cell_length_c                   10.9144(3)
_cell_angle_alpha                63.350(2)
_cell_angle_beta                 71.042(2)
_cell_angle_gamma                82.5615(19)
_cell_volume                     803.65(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    12740
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.5724
_cell_measurement_theta_min      3.3329
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.864
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61400
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.109
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             492
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.905
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15243
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.905
_diffrn_reflns_theta_full        28.000
_diffrn_reflns_theta_max         30.641
_diffrn_reflns_theta_min         3.340
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.2833
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.905
_diffrn_measurement_details      
'#__ type_ start__ end____ width___ exp.time_ 1 omega 25.00 88.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - 14.4190 38.0000 -150.0000 63 #__ type_ start__ end____ width___ exp.time_ 2 omega -3.00 82.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - 14.4190 55.0000 147.0000 85 #__ type_ start__ end____ width___ exp.time_ 3 omega -18.00 92.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - 14.4190 77.0000 -60.0000 110 #__ type_ start__ end____ width___ exp.time_ 4 omega -59.00 44.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - 14.4190 -55.0000 -175.0000 103 #__ type_ start__ end____ width___ exp.time_ 5 omega -30.00 40.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - 14.4190 -38.0000 0.0000 70 #__ type_ start__ end____ width___ exp.time_ 6 omega 34.00 76.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - 14.4190 179.0000 30.0000 42 #__ type_ start__ end____ width___ exp.time_ 7 omega 5.00 85.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - 14.4190 38.0000 90.0000 80 #__ type_ start__ end____ width___ exp.time_ 8 omega 34.00 88.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - 14.4190 179.0000 -150.0000 54 #__ type_ start__ end____ width___ exp.time_ 9 omega -91.00 -52.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - -15.2002 153.0000 -126.0000 39 #__ type_ start__ end____ width___ exp.time_ 10 omega -93.00 -67.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - -15.2002 155.0000 49.0000 26'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0782193000
_diffrn_orient_matrix_UB_12      0.0226442000
_diffrn_orient_matrix_UB_13      -0.0120262000
_diffrn_orient_matrix_UB_21      0.0334940000
_diffrn_orient_matrix_UB_22      0.0711519000
_diffrn_orient_matrix_UB_23      -0.0488486000
_diffrn_orient_matrix_UB_31      0.0231951000
_diffrn_orient_matrix_UB_32      -0.0207162000
_diffrn_orient_matrix_UB_33      -0.0572991000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4402
_reflns_number_total             4490
_reflns_odcompleteness_completeness 99.35
_reflns_odcompleteness_iscentric 0
_reflns_odcompleteness_theta     28.02
_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       
'CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40)'
_computing_data_collection       
'CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40)'
_computing_data_reduction        
'CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40)'
_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    'ShelXS-1997 (Sheldrick, 2008)'
_refine_diff_density_max         1.029
_refine_diff_density_min         -0.792
_refine_diff_density_rms         0.110
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         4490
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0168
_refine_ls_R_factor_gt           0.0162
_refine_ls_restrained_S_all      1.067
_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)+(0.0127P)²+0.6471P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0362
_refine_ls_wR_factor_ref         0.0365
_refine_special_details          ?
_olex2_refinement_description    
;
The hydrogens on the coordinated water (O501) were located in 
a difference map.
They were allowed to refine with a distance restraint (DFIX 0.85) 
and thermal parameters equal to 1.5 times that of O501 to which 
they were attached.

1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Restrained distances
 O501-H50A = O501-H50B
 0.85 with sigma of 0.008
3.a Aromatic/amide H refined with riding coordinates:
 C104(H104), C105(H105), C204(H204), C205(H205), C304(H304), C305(H305),
 C402(H402)
3.b Idealised Me refined as rotating group:
 C404(H40A,H40B,H40C), C405(H40D,H40E,H40F)
;
_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
Yb1 Yb 0.36393(2) 0.56591(2) 0.33189(2) 0.00628(3) Uani 1 1 d . . . . .
O101 O 0.54610(18) 0.50008(15) 0.15242(14) 0.0107(3) Uani 1 1 d . . . . .
O102 O 0.65383(18) 0.62757(14) 0.22407(13) 0.0095(3) Uani 1 1 d . . . . .
C102 C 0.6710(2) 0.55244(19) 0.15424(18) 0.0085(3) Uani 1 1 d . . . . .
C103 C 0.8416(2) 0.5239(2) 0.07546(19) 0.0092(4) Uani 1 1 d . . . . .
C104 C 0.8623(3) 0.4295(2) 0.0112(2) 0.0113(4) Uani 1 1 d . . . . .
H104 H 0.768836 0.381346 0.019082 0.014 Uiso 1 1 calc R . . . .
C105 C 1.0218(3) 0.4067(2) -0.0646(2) 0.0112(4) Uani 1 1 d . . . . .
H105 H 1.036902 0.343041 -0.109326 0.013 Uiso 1 1 calc R . . . .
O201 O 0.33115(19) 0.75557(15) 0.11864(14) 0.0124(3) Uani 1 1 d . . . . .
O202 O 0.10719(19) 0.69331(15) 0.30744(14) 0.0113(3) Uani 1 1 d . . . . .
C202 C 0.1807(3) 0.7749(2) 0.17562(19) 0.0089(3) Uani 1 1 d . . . . .
C203 C 0.0864(3) 0.8933(2) 0.08649(19) 0.0095(4) Uani 1 1 d . . . . .
C204 C 0.1678(3) 0.9810(2) -0.0575(2) 0.0133(4) Uani 1 1 d . . . . .
H204 H 0.282853 0.968112 -0.096626 0.016 Uiso 1 1 calc R . . . .
C205 C 0.0819(3) 1.0872(2) -0.1443(2) 0.0124(4) Uani 1 1 d . . . . .
H205 H 0.137812 1.146088 -0.242528 0.015 Uiso 1 1 calc R . . . .
O301 O 0.50183(19) 0.37484(15) 0.45981(14) 0.0126(3) Uani 1 1 d . . . . .
O302 O 0.61524(19) 0.23438(15) 0.63145(14) 0.0118(3) Uani 1 1 d . . . . .
C302 C 0.5481(2) 0.2519(2) 0.53775(19) 0.0078(3) Uani 1 1 d . . . . .
C303 C 0.5246(3) 0.1216(2) 0.51783(19) 0.0093(4) Uani 1 1 d . . . . .
C304 C 0.5173(3) 0.1384(2) 0.38527(19) 0.0106(4) Uani 1 1 d . . . . .
H304 H 0.529553 0.232789 0.307069 0.013 Uiso 1 1 calc R . . . .
C305 C 0.4924(3) 0.0180(2) 0.36809(19) 0.0109(4) Uani 1 1 d . . . . .
H305 H 0.486839 0.029957 0.278110 0.013 Uiso 1 1 calc R . . . .
O401 O 0.20967(19) 0.40763(15) 0.32199(15) 0.0124(3) Uani 1 1 d . . . . .
C402 C 0.2358(3) 0.3320(2) 0.2540(2) 0.0128(4) Uani 1 1 d . . . . .
H402 H 0.336399 0.348375 0.177650 0.015 Uiso 1 1 calc R . . . .
N403 N 0.1308(2) 0.23085(18) 0.28295(19) 0.0144(3) Uani 1 1 d . . . . .
C404 C 0.1698(3) 0.1406(2) 0.2046(2) 0.0205(5) Uani 1 1 d . . . . .
H40A H 0.276595 0.172932 0.129138 0.031 Uiso 1 1 calc GR . . . .
H40B H 0.082263 0.150227 0.160911 0.031 Uiso 1 1 calc GR . . . .
H40C H 0.176595 0.038163 0.271255 0.031 Uiso 1 1 calc GR . . . .
C405 C -0.0287(3) 0.2073(3) 0.3946(3) 0.0246(5) Uani 1 1 d . . . . .
H40D H -0.010122 0.165549 0.488869 0.037 Uiso 1 1 calc GR . . . .
H40E H -0.098034 0.139744 0.392041 0.037 Uiso 1 1 calc GR . . . .
H40F H -0.085075 0.300715 0.377790 0.037 Uiso 1 1 calc GR . . . .
O501 O 0.18745(19) 0.47287(16) 0.56579(14) 0.0120(3) Uani 1 1 d D . . . .
H50A H 0.232(3) 0.439(3) 0.633(2) 0.018 Uiso 1 1 d DR . . . .
H50B H 0.0964(18) 0.425(2) 0.603(3) 0.018 Uiso 1 1 d DR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Yb1 O101 2.3738(13) . ?
Yb1 O102 2.3906(15) . ?
Yb1 O201 2.3440(13) . ?
Yb1 O202 2.4230(14) . ?
Yb1 O301 2.2747(13) . ?
Yb1 O302 2.2914(14) 2_666 ?
Yb1 C302 3.0826(19) 2_666 ?
Yb1 O401 2.2721(15) . ?
Yb1 O501 2.3187(14) . ?
O101 C102 1.260(3) . ?
O102 C102 1.273(2) . ?
C102 C103 1.495(3) . ?
C103 C104 1.392(3) . ?
C103 C105 1.386(3) 2_765 ?
C104 H104 0.9500 . ?
C104 C105 1.394(3) . ?
C105 H105 0.9500 . ?
O201 C202 1.262(2) . ?
O202 C202 1.277(2) . ?
C202 C203 1.502(3) . ?
C203 C204 1.394(3) . ?
C203 C205 1.393(3) 2_575 ?
C204 H204 0.9500 . ?
C204 C205 1.390(3) . ?
C205 H205 0.9500 . ?
O301 C302 1.262(2) . ?
O302 C302 1.262(2) . ?
C302 C303 1.492(3) . ?
C303 C304 1.400(3) . ?
C303 C305 1.398(2) 2_656 ?
C304 H304 0.9500 . ?
C304 C305 1.379(3) . ?
C305 H305 0.9500 . ?
O401 C402 1.251(2) . ?
C402 H402 0.9500 . ?
C402 N403 1.317(3) . ?
N403 C404 1.464(3) . ?
N403 C405 1.459(3) . ?
C404 H40A 0.9800 . ?
C404 H40B 0.9800 . ?
C404 H40C 0.9800 . ?
C405 H40D 0.9800 . ?
C405 H40E 0.9800 . ?
C405 H40F 0.9800 . ?
O501 H50A 0.845(8) . ?
O501 H50B 0.850(8) . ?

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
O101 Yb1 O102 55.05(5) . . ?
O101 Yb1 O202 122.60(5) . . ?
O101 Yb1 C302 127.04(5) . 2_666 ?
O102 Yb1 O202 135.78(4) . . ?
O102 Yb1 C302 72.00(5) . 2_666 ?
O201 Yb1 O101 77.19(5) . . ?
O201 Yb1 O102 85.56(5) . . ?
O201 Yb1 O202 55.10(5) . . ?
O201 Yb1 C302 99.37(5) . 2_666 ?
O202 Yb1 C302 93.41(5) . 2_666 ?
O301 Yb1 O101 77.58(5) . . ?
O301 Yb1 O102 73.08(5) . . ?
O301 Yb1 O201 153.38(5) . . ?
O301 Yb1 O202 150.09(5) . . ?
O301 Yb1 O302 110.31(5) . 2_666 ?
O301 Yb1 C302 89.13(5) . 2_666 ?
O301 Yb1 O501 75.07(5) . . ?
O302 Yb1 O101 127.66(5) 2_666 . ?
O302 Yb1 O102 77.22(5) 2_666 . ?
O302 Yb1 O201 79.19(5) 2_666 . ?
O302 Yb1 O202 76.27(5) 2_666 . ?
O302 Yb1 C302 21.31(5) 2_666 2_666 ?
O302 Yb1 O501 84.49(5) 2_666 . ?
O401 Yb1 O101 76.06(5) . . ?
O401 Yb1 O102 130.35(5) . . ?
O401 Yb1 O201 92.19(5) . . ?
O401 Yb1 O202 75.96(5) . . ?
O401 Yb1 O301 89.85(5) . . ?
O401 Yb1 O302 150.79(5) . 2_666 ?
O401 Yb1 C302 155.90(5) . 2_666 ?
O401 Yb1 O501 80.50(5) . . ?
O501 Yb1 O101 143.74(5) . . ?
O501 Yb1 O102 134.56(5) . . ?
O501 Yb1 O201 131.41(5) . . ?
O501 Yb1 O202 76.66(5) . . ?
O501 Yb1 C302 75.98(5) . 2_666 ?
C102 O101 Yb1 92.24(11) . . ?
C102 O102 Yb1 91.14(12) . . ?
O101 C102 O102 120.82(18) . . ?
O101 C102 C103 119.63(17) . . ?
O102 C102 C103 119.55(18) . . ?
C104 C103 C102 119.89(19) . . ?
C105 C103 C102 119.83(17) 2_765 . ?
C105 C103 C104 120.28(18) 2_765 . ?
C103 C104 H104 120.4 . . ?
C103 C104 C105 119.2(2) . . ?
C105 C104 H104 120.4 . . ?
C103 C105 C104 120.53(18) 2_765 . ?
C103 C105 H105 119.7 2_765 . ?
C104 C105 H105 119.7 . . ?
C202 O201 Yb1 94.11(11) . . ?
C202 O202 Yb1 90.07(12) . . ?
O201 C202 O202 120.65(17) . . ?
O201 C202 C203 119.53(16) . . ?
O202 C202 C203 119.81(18) . . ?
C204 C203 C202 119.21(18) . . ?
C205 C203 C202 120.93(17) 2_575 . ?
C205 C203 C204 119.81(17) 2_575 . ?
C203 C204 H204 119.8 . . ?
C205 C204 C203 120.49(19) . . ?
C205 C204 H204 119.8 . . ?
C203 C205 H205 120.2 2_575 . ?
C204 C205 C203 119.69(18) . 2_575 ?
C204 C205 H205 120.2 . . ?
C302 O301 Yb1 166.43(14) . . ?
C302 O302 Yb1 117.38(12) . 2_666 ?
O301 C302 Yb1 81.49(11) . 2_666 ?
O301 C302 C303 118.99(17) . . ?
O302 C302 Yb1 41.30(9) . 2_666 ?
O302 C302 O301 122.72(18) . . ?
O302 C302 C303 118.29(16) . . ?
C303 C302 Yb1 159.43(12) . 2_666 ?
C304 C303 C302 120.23(16) . . ?
C305 C303 C302 120.28(16) 2_656 . ?
C305 C303 C304 119.48(18) 2_656 . ?
C303 C304 H304 120.0 . . ?
C305 C304 C303 120.06(17) . . ?
C305 C304 H304 120.0 . . ?
C303 C305 H305 119.8 2_656 . ?
C304 C305 C303 120.46(17) . 2_656 ?
C304 C305 H305 119.8 . . ?
C402 O401 Yb1 135.16(14) . . ?
O401 C402 H402 118.4 . . ?
O401 C402 N403 123.2(2) . . ?
N403 C402 H402 118.4 . . ?
C402 N403 C404 121.34(19) . . ?
C402 N403 C405 120.10(18) . . ?
C405 N403 C404 118.6(2) . . ?
N403 C404 H40A 109.5 . . ?
N403 C404 H40B 109.5 . . ?
N403 C404 H40C 109.5 . . ?
H40A C404 H40B 109.5 . . ?
H40A C404 H40C 109.5 . . ?
H40B C404 H40C 109.5 . . ?
N403 C405 H40D 109.5 . . ?
N403 C405 H40E 109.5 . . ?
N403 C405 H40F 109.5 . . ?
H40D C405 H40E 109.5 . . ?
H40D C405 H40F 109.5 . . ?
H40E C405 H40F 109.5 . . ?
Yb1 O501 H50A 117.1(19) . . ?
Yb1 O501 H50B 130.5(18) . . ?
H50A O501 H50B 104(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
O501 H50A O102 0.845(8) 1.928(9) 2.771(2) 176(3) 2_666
O501 H50B O202 0.850(8) 1.949(8) 2.798(2) 177(3) 2_566

_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_rc1_twin1_hklf5
_database_code_depnum_ccdc_archive 'CCDC 1537042'
_audit_update_record             
;
2017-03-09 deposited with the CCDC.
2017-04-11 downloaded from the CCDC.
;
_audit_creation_date             2017-03-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.02.23 svn.r3390 for OlexSys, GUI svn.r5320)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H5 O6 Yb'
_chemical_formula_sum            'C9 H5 O6 Yb'
_chemical_formula_weight         382.17
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 N2 O2 Yb'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Yb Yb -7.2108 4.4329 '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                   10.56825(17)
_cell_length_b                   12.66272(19)
_cell_length_c                   6.62290(13)
_cell_angle_alpha                90
_cell_angle_beta                 95.2274(17)
_cell_angle_gamma                90
_cell_volume                     882.61(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5305
_cell_measurement_temperature    296(3)
_cell_measurement_theta_max      77.5500
_cell_measurement_theta_min      4.1790
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    19.776
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.28995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.876
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             708
_exptl_crystal_size_max          0.1
_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  ?
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            3200
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.644
_diffrn_reflns_theta_min         4.201
_diffrn_ambient_temperature      296(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2833
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1350213000
_diffrn_orient_matrix_UB_12      -0.0382177000
_diffrn_orient_matrix_UB_13      0.0725536000
_diffrn_orient_matrix_UB_21      0.0491870000
_diffrn_orient_matrix_UB_22      0.1142940000
_diffrn_orient_matrix_UB_23      -0.0079085000
_diffrn_orient_matrix_UB_31      -0.0282293000
_diffrn_orient_matrix_UB_32      0.0165419000
_diffrn_orient_matrix_UB_33      0.2218477000
loop_
_diffrn_oxdiff_twin_id
_diffrn_oxdiff_twin_ratio
_diffrn_oxdiff_twin_reflns_isolated
_diffrn_oxdiff_twin_reflns_overlapped
1 0.6644 4033 4763
2 0.3356 4027 4763

_diffrn_oxdiff_twin_integration_method simultaneous
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2625
_reflns_number_total             3200
_reflns_special_details          
;
 _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       
'CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01)'
_computing_data_collection       
'CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01)'
_computing_data_reduction        
'CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01)'
_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         2.993
_refine_diff_density_min         -1.777
_refine_diff_density_rms         0.330
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         3200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0561
_refine_ls_restrained_S_all      1.066
_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)+(0.1193P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1522
_refine_ls_wR_factor_ref         0.1554
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
All the samples of the blocks investigated were twinned to some extent making 
the diffraction from the small crystals very weak.
The most promising sample with the least amount of twinning was recorded and 
the structural refinement appears here.

The asymmetric unit contains a terephthalate, a Yb and a formate. Four times 
all this in the unit cell.

Matrices relating the two twin components were
1  1.0000  0.0000  0.0000  0.0000  1.0000  0.0000  0.0000  0.0000  1.0000
2 -1.0000  0.0007 -0.2907 -0.0007 -1.0001 -0.0003  0.0004 -0.0002  1.0001

The volume of the two domains in the crystal from the integration is
  _diffrn_oxdiff_twin_id
  _diffrn_oxdiff_twin_ratio
  _diffrn_oxdiff_twin_reflns_isolated
  _diffrn_oxdiff_twin_reflns_overlapped
 1 0.6644 4033 4763
 2 0.3356 4027 4763

Twinned data refinement with Shelxl/Olex2 from the refinement of the BASF 
on F2 (see Shelx manual for details)
The refined scale factors (twin ratios) were   0.7145(18) 0.2855(18)

1. Twinned data refinement
 Scales: 0.7145(18)
 0.2855(18)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8), C12(H12)
;
_atom_sites_solution_hydrogens   geom
_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
Yb1 Yb 0.92795(4) 0.62845(3) 0.09726(8) 0.0115(2) Uani 1 1 d . . . . .
O1 O 0.8303(7) 0.6139(7) 0.3762(13) 0.0196(15) Uani 1 1 d . . . . .
O2 O 0.7632(6) 0.7588(6) 0.5294(12) 0.0177(14) Uani 1 1 d . . . . .
C2 C 0.7436(10) 0.6737(8) 0.4376(17) 0.016(2) Uani 1 1 d . . . . .
C3 C 0.6090(10) 0.6396(9) 0.3856(17) 0.018(2) Uani 1 1 d . . . . .
C4 C 0.5813(9) 0.5451(9) 0.2882(18) 0.020(2) Uani 1 1 d . . . . .
H4 H 0.647376 0.500584 0.259798 0.023 Uiso 1 1 calc R . . . .
C5 C 0.4572(10) 0.5153(9) 0.2318(19) 0.020(2) Uani 1 1 d . . . . .
H5 H 0.440290 0.450437 0.169102 0.024 Uiso 1 1 calc R . . . .
C6 C 0.3572(10) 0.5825(9) 0.2692(19) 0.020(2) Uani 1 1 d . . . . .
C7 C 0.3825(10) 0.6775(9) 0.3705(19) 0.021(2) Uani 1 1 d . . . . .
H7 H 0.316022 0.721547 0.399193 0.026 Uiso 1 1 calc R . . . .
C8 C 0.5071(10) 0.7064(9) 0.4286(19) 0.021(2) Uani 1 1 d . . . . .
H8 H 0.523976 0.769961 0.496233 0.025 Uiso 1 1 calc R . . . .
O9 O 0.1358(7) 0.6158(7) 0.2183(15) 0.0244(18) Uani 1 1 d . . . . .
C9 C 0.2244(9) 0.5503(9) 0.1962(19) 0.019(2) Uani 1 1 d . . . . .
O10 O 0.2113(7) 0.4621(6) 0.1133(14) 0.0216(16) Uani 1 1 d . . . . .
O11 O 0.9896(6) 0.7120(6) -0.2202(12) 0.0179(15) Uani 1 1 d . . . . .
O12 O 1.0453(8) 0.5484(6) -0.1762(14) 0.0215(16) Uani 1 1 d . . . . .
C12 C 1.0406(10) 0.6313(8) -0.2804(18) 0.019(2) Uani 1 1 d . . . . .
H12 H 1.075864 0.632175 -0.404020 0.022 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
Yb1 Yb1 3.8625(8) 3_765 ?
Yb1 O1 2.204(8) . ?
Yb1 O2 2.265(7) 4_575 ?
Yb1 O9 2.274(8) 1_655 ?
Yb1 O10 2.247(8) 3_665 ?
Yb1 O11 2.413(8) 4_576 ?
Yb1 O11 2.493(8) . ?
Yb1 O12 2.501(9) . ?
Yb1 O12 2.312(8) 3_765 ?
O1 C2 1.283(13) . ?
O2 C2 1.245(14) . ?
C2 C3 1.496(14) . ?
C3 C4 1.378(16) . ?
C3 C8 1.419(15) . ?
C4 H4 0.9300 . ?
C4 C5 1.384(14) . ?
C5 H5 0.9300 . ?
C5 C6 1.396(15) . ?
C6 C7 1.391(16) . ?
C6 C9 1.499(13) . ?
C7 H7 0.9300 . ?
C7 C8 1.387(15) . ?
C8 H8 0.9300 . ?
O9 C9 1.269(13) . ?
C9 O10 1.247(14) . ?
O11 C12 1.238(14) . ?
O12 C12 1.254(14) . ?
C12 H12 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 Yb1 Yb1 116.0(2) . 3_765 ?
O1 Yb1 O2 79.0(3) . 4_575 ?
O1 Yb1 O9 102.1(3) . 1_655 ?
O1 Yb1 O10 98.5(3) . 3_665 ?
O1 Yb1 O11 157.0(3) . . ?
O1 Yb1 O11 77.0(3) . 4_576 ?
O1 Yb1 O12 77.7(3) . 3_765 ?
O1 Yb1 O12 150.9(3) . . ?
O2 Yb1 Yb1 141.6(2) 4_575 3_765 ?
O2 Yb1 O9 144.6(3) 4_575 1_655 ?
O2 Yb1 O11 79.6(3) 4_575 . ?
O2 Yb1 O11 74.9(3) 4_575 4_576 ?
O2 Yb1 O12 137.0(3) 4_575 3_765 ?
O2 Yb1 O12 122.3(3) 4_575 . ?
O9 Yb1 Yb1 70.2(2) 1_655 3_765 ?
O9 Yb1 O11 71.0(3) 1_655 4_576 ?
O9 Yb1 O11 90.5(3) 1_655 . ?
O9 Yb1 O12 72.5(3) 1_655 . ?
O9 Yb1 O12 76.0(3) 1_655 3_765 ?
O10 Yb1 Yb1 67.61(19) 3_665 3_765 ?
O10 Yb1 O2 75.6(3) 3_665 4_575 ?
O10 Yb1 O9 137.7(3) 3_665 1_655 ?
O10 Yb1 O11 150.4(3) 3_665 4_576 ?
O10 Yb1 O11 84.3(3) 3_665 . ?
O10 Yb1 O12 71.6(3) 3_665 . ?
O10 Yb1 O12 72.9(3) 3_665 3_765 ?
O11 Yb1 Yb1 140.85(16) 4_576 3_765 ?
O11 Yb1 Yb1 86.27(19) . 3_765 ?
O11 Yb1 O11 89.31(13) 4_576 . ?
O11 Yb1 O12 51.4(3) . . ?
O11 Yb1 O12 125.0(3) 4_576 . ?
O12 Yb1 Yb1 38.3(2) 3_765 3_765 ?
O12 Yb1 Yb1 34.98(19) . 3_765 ?
O12 Yb1 O11 132.5(3) 3_765 4_576 ?
O12 Yb1 O11 124.5(3) 3_765 . ?
O12 Yb1 O12 73.3(3) 3_765 . ?
C2 O1 Yb1 128.2(7) . . ?
C2 O2 Yb1 137.2(7) . 4_576 ?
O1 C2 C3 116.6(10) . . ?
O2 C2 O1 125.0(9) . . ?
O2 C2 C3 118.3(10) . . ?
C4 C3 C2 121.0(10) . . ?
C4 C3 C8 118.6(10) . . ?
C8 C3 C2 120.3(10) . . ?
C3 C4 H4 119.4 . . ?
C3 C4 C5 121.3(10) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 119.9(11) . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C9 118.5(10) . . ?
C7 C6 C5 119.9(10) . . ?
C7 C6 C9 121.6(10) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 C6 119.8(10) . . ?
C8 C7 H7 120.1 . . ?
C3 C8 H8 119.8 . . ?
C7 C8 C3 120.4(11) . . ?
C7 C8 H8 119.8 . . ?
C9 O9 Yb1 134.8(7) . 1_455 ?
O9 C9 C6 117.7(10) . . ?
O10 C9 C6 116.7(9) . . ?
O10 C9 O9 125.6(10) . . ?
C9 O10 Yb1 140.4(7) . 3_665 ?
Yb1 O11 Yb1 134.3(3) 4_575 . ?
C12 O11 Yb1 94.4(7) . . ?
C12 O11 Yb1 129.4(7) . 4_575 ?
Yb1 O12 Yb1 106.7(3) 3_765 . ?
C12 O12 Yb1 158.9(8) . 3_765 ?
C12 O12 Yb1 93.6(7) . . ?
O11 C12 O12 120.7(11) . . ?
O11 C12 H12 119.7 . . ?
O12 C12 H12 119.7 . . ?

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
Yb1 O1 C2 O2 -82.1(13) . . . . ?
Yb1 O1 C2 C3 95.0(11) . . . . ?
Yb1 O2 C2 O1 12.5(18) 4_576 . . . ?
Yb1 O2 C2 C3 -164.6(7) 4_576 . . . ?
Yb1 O9 C9 C6 167.4(9) 1_455 . . . ?
Yb1 O9 C9 O10 -10(2) 1_455 . . . ?
Yb1 O11 C12 O12 -1.1(11) . . . . ?
Yb1 O11 C12 O12 -167.0(7) 4_575 . . . ?
Yb1 O12 C12 O11 164.9(14) 3_765 . . . ?
Yb1 O12 C12 O11 1.1(11) . . . . ?
O1 C2 C3 C4 4.1(16) . . . . ?
O1 C2 C3 C8 -173.3(10) . . . . ?
O2 C2 C3 C4 -178.5(10) . . . . ?
O2 C2 C3 C8 4.0(16) . . . . ?
C2 C3 C4 C5 -177.2(11) . . . . ?
C2 C3 C8 C7 176.5(11) . . . . ?
C3 C4 C5 C6 1.5(19) . . . . ?
C4 C3 C8 C7 -1.0(18) . . . . ?
C4 C5 C6 C7 -2.6(19) . . . . ?
C4 C5 C6 C9 176.8(11) . . . . ?
C5 C6 C7 C8 1.9(19) . . . . ?
C5 C6 C9 O9 -174.9(12) . . . . ?
C5 C6 C9 O10 3.0(17) . . . . ?
C6 C7 C8 C3 -0.1(19) . . . . ?
C6 C9 O10 Yb1 -159.6(9) . . . 3_665 ?
C7 C6 C9 O9 4.4(18) . . . . ?
C7 C6 C9 O10 -177.6(12) . . . . ?
C8 C3 C4 C5 0.3(17) . . . . ?
O9 C9 O10 Yb1 18(2) . . . 3_665 ?
C9 C6 C7 C8 -177.5(12) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.7145(18)
2 0.2855(18)

####################################################################### 
# 
# 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_mb2_twin1_hklf5
_audit_block_doi                 10.5517/ccdc.csd.cc14hcnn
_database_code_depnum_ccdc_archive 'CCDC 1057461'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1002/anie.201600896 2016
_audit_update_record             
;
2015-12-16 deposited with the CCDC.
2017-04-11 downloaded from the CCDC.
;
_audit_creation_date             2015-07-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3151 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H13 N O7 Yb, 0.5(H2 O)'
_chemical_formula_sum            'C15 H14 N O7.50 Yb'
_chemical_formula_weight         501.31
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C15 H10N1 O8 Yb'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Yb Yb -0.3850 5.5486 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   18.2950(4)
_cell_length_b                   10.8482(2)
_cell_length_c                   17.3984(4)
_cell_angle_alpha                90
_cell_angle_beta                 101.395(2)
_cell_angle_gamma                90
_cell_volume                     3384.96(13)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6851
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.3060
_cell_measurement_theta_min      3.4070
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.565
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67856
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.967
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1928
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            40716
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.419
_diffrn_reflns_theta_min         3.074
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2833
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -6.00  108.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       23.1033   77.0000  150.0000 228

#__ type_ start__ end____ width___ exp.time_
  2 omega  -22.00  118.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       23.1033   77.0000  -60.0000 280

#__ type_ start__ end____ width___ exp.time_
  3 omega   42.00   67.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.8220   77.0000 -120.0000 50

#__ type_ start__ end____ width___ exp.time_
  4 omega   -9.00   19.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.8220   77.0000 -120.0000 56

#__ type_ start__ end____ width___ exp.time_
  5 omega  -64.00   69.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.8220   77.0000   30.0000 266
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0328388000
_diffrn_orient_matrix_UB_12      -0.0354829000
_diffrn_orient_matrix_UB_13      -0.0014490000
_diffrn_orient_matrix_UB_21      -0.0188485000
_diffrn_orient_matrix_UB_22      0.0530794000
_diffrn_orient_matrix_UB_23      0.0098677000
_diffrn_orient_matrix_UB_31      -0.0114857000
_diffrn_orient_matrix_UB_32      0.0142109000
_diffrn_orient_matrix_UB_33      -0.0404364000
loop_
_diffrn_oxdiff_twin_id
_diffrn_oxdiff_twin_ratio
_diffrn_oxdiff_twin_reflns_isolated
_diffrn_oxdiff_twin_reflns_overlapped
1 0.8291 12002 16698
2 0.1709 12016 16698

_diffrn_oxdiff_twin_integration_method simultaneous
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7025
_reflns_number_total             8841
_reflns_special_details          
;
 _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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         2.636
_refine_diff_density_min         -1.456
_refine_diff_density_rms         0.292
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         8841
_refine_ls_number_restraints     32
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0358
_refine_ls_restrained_S_all      1.049
_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)+(0.0782P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1042
_refine_ls_wR_factor_ref         0.1155
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;

The crystal chosen had a twin component. The relationship between the UB matrix and the 
two twin orientations are 
Twin 1  1.0000  0.0000  0.0000  0.0000  1.0000  0.0000  0.0000  0.0000  1.0000
Twin 2 -0.9994 -0.0001 -0.4142  0.0001 -1.0001  0.0000 -0.0001  0.0001  0.9994

From the twin log generated by CrysalisPro
Twin analysis: Component 1 with component 2
TL  =UB[1]-1*UB[2]:  -0.9994  -0.0000  -0.4141    -0.0001  -1.0002  -0.0000    -0.0001  -0.0001   0.9994   det 0.999026
TL-1=UB[2]*UB[1]-1:  -1.0005   0.0001  -0.4146     0.0001  -0.9998   0.0000    -0.0001  -0.0001   1.0006   det 1.000975
the two orientations are related by a
rotation = -179.9892 deg around the following vectors: 
Reciprocal space (hkl): -0.2036 0.0002 0.9790
Direct space (uvw)    : -0.0001 -0.0000 1.0000

Twinned data refinement
The scale factors (twin ratios) were   0.8746(5) : 0.1254(5)

The integration of the data was conducted with the twinning suite in the Crysalis Pro software 
and refined with Olex2

The coordinated DMF had cigar shaped thermal ellipsoids and was refined with SIMU and DELU 
restraints to give it reasonable thermal parameters.

Electron density not close enough to be metal bound or part of the ligand was modeled as a 
partially occupied water (half occupancy). Hydrogens were placed at calculated positions on 
this water. The partially occupied water molecule was refined behind a PART -1 instruction 
as it is close to a symmetry related water but this is possible as it is only half occupied 
and lies in either one position or the other in the crystal lattice.



1. Twinned data refinement
 Scales: 0.8746(5) 0.1254(5)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
3. Rigid bond restraints
 O301, C302, N303, C304, C305
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Uiso/Uaniso restraints and constraints
O301 \\sim C302 \\sim N303 \\sim C304 \\sim C305: within 1.7A with sigma of
0.002 and sigma for terminal atoms of 0.004
5. Others
 Fixed Sof: O1(0.5) H1A(0.5) H1B(0.5)
6.a Free rotating group:
 O1(H1A,H1B)
6.b Aromatic/amide H refined with riding coordinates:
 C205(H205), C302(H302), C104(H104), C108(H108), C107(H107), C105(H105),
 C204(H204)
6.c Idealised Me refined as rotating group:
 C305(H30A,H30B,H30C), C304(H30D,H30E,H30F)
;
_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
Yb1 Yb 0.48898(2) 0.40159(2) 0.10204(2) 0.00731(10) Uani 1 1 d . . . . .
C102 C 0.6134(3) 0.6078(4) 0.0830(4) 0.0131(11) Uani 1 1 d . . . . .
O201 O 0.5632(2) 0.3429(4) 0.0212(2) 0.0158(8) Uani 1 1 d . . . . .
O202 O 0.5834(2) 0.4230(3) -0.0913(2) 0.0161(8) Uani 1 1 d . . . . .
O101 O 0.5757(2) 0.5494(4) 0.1251(2) 0.0144(8) Uani 1 1 d . . . . .
O110 O 0.9259(2) 0.8938(3) 0.1972(2) 0.0117(8) Uani 1 1 d . . . . .
O0AA O 0.9150(2) 0.8085(3) 0.3104(2) 0.0150(8) Uani 1 1 d . . . . .
C106 C 0.8198(3) 0.7699(5) 0.1990(3) 0.0128(10) Uani 1 1 d . . . . .
C202 C 0.6033(3) 0.3600(5) -0.0296(3) 0.0118(10) Uani 1 1 d . . . . .
C109 C 0.8919(3) 0.8273(5) 0.2385(3) 0.0107(10) Uani 1 1 d . . . . .
C205 C 0.7200(3) 0.2950(5) -0.0746(3) 0.0161(11) Uani 1 1 d . . . . .
H205 H 0.6996 0.3258 -0.1255 0.019 Uiso 1 1 calc R . . . .
O102 O 0.5966(2) 0.6197(3) 0.0099(2) 0.0156(8) Uani 1 1 d . . . . .
C103 C 0.6849(3) 0.6661(5) 0.1240(3) 0.0132(10) Uani 1 1 d . . . . .
O301 O 0.4604(3) 0.1932(3) 0.0971(2) 0.0202(8) Uani 1 1 d . U . . .
C302 C 0.5044(5) 0.1054(5) 0.0992(4) 0.0269(10) Uani 1 1 d . U . . .
H302 H 0.5529 0.1224 0.0901 0.032 Uiso 1 1 calc R . . . .
C104 C 0.7171(3) 0.7607(5) 0.0877(3) 0.0158(11) Uani 1 1 d . . . . .
H104 H 0.6933 0.7894 0.0374 0.019 Uiso 1 1 calc R . . . .
C108 C 0.7200(3) 0.6237(5) 0.1981(3) 0.0152(11) Uani 1 1 d . . . . .
H108 H 0.6979 0.5597 0.2230 0.018 Uiso 1 1 calc R . . . .
C203 C 0.6794(3) 0.3027(5) -0.0147(3) 0.0130(10) Uani 1 1 d . . . . .
C107 C 0.7870(3) 0.6751(5) 0.2351(3) 0.0161(11) Uani 1 1 d . . . . .
H107 H 0.8109 0.6458 0.2853 0.019 Uiso 1 1 calc R . . . .
C105 C 0.7837(3) 0.8126(5) 0.1253(3) 0.0158(11) Uani 1 1 d . . . . .
H105 H 0.8052 0.8779 0.1009 0.019 Uiso 1 1 calc R . . . .
C204 C 0.7097(3) 0.2579(5) 0.0593(3) 0.0173(11) Uani 1 1 d . . . . .
H204 H 0.6820 0.2636 0.0999 0.021 Uiso 1 1 calc R . . . .
N303 N 0.4880(3) -0.0107(5) 0.1134(3) 0.0360(11) Uani 1 1 d . U . . .
C305 C 0.5416(6) -0.1082(6) 0.1131(5) 0.0492(18) Uani 1 1 d . U . . .
H30A H 0.5859 -0.0749 0.0965 0.074 Uiso 1 1 calc GR . . . .
H30B H 0.5195 -0.1730 0.0766 0.074 Uiso 1 1 calc GR . . . .
H30C H 0.5560 -0.1428 0.1660 0.074 Uiso 1 1 calc GR . . . .
C304 C 0.4145(5) -0.0407(7) 0.1258(6) 0.0571(18) Uani 1 1 d . U . . .
H30D H 0.3949 0.0285 0.1518 0.086 Uiso 1 1 calc GR . . . .
H30E H 0.4170 -0.1144 0.1588 0.086 Uiso 1 1 calc GR . . . .
H30F H 0.3814 -0.0566 0.0751 0.086 Uiso 1 1 calc GR . . . .
O1 O 0.5552(7) 0.2937(8) -0.2380(6) 0.037(2) Uani 0.5 1 d . . P . .
H1A H 0.5649 0.3257 -0.1913 0.056 Uiso 0.5 1 d G . P . .
H1B H 0.5548 0.3514 -0.2728 0.056 Uiso 0.5 1 d G . P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Yb1 Yb1 4.2302(4) 5_665 ?
Yb1 O201 2.232(4) . ?
Yb1 O202 2.304(4) 5_665 ?
Yb1 O101 2.235(4) . ?
Yb1 O110 2.199(4) 3_445 ?
Yb1 O0AA 2.317(4) 4_645 ?
Yb1 C202 3.207(5) 5_665 ?
Yb1 O102 2.257(4) 5_665 ?
Yb1 O301 2.317(4) . ?
C102 O101 1.271(7) . ?
C102 O102 1.254(7) . ?
C102 C103 1.501(7) . ?
O201 C202 1.269(6) . ?
O202 Yb1 2.304(4) 5_665 ?
O202 C202 1.264(7) . ?
O110 Yb1 2.199(4) 3 ?
O110 C109 1.265(6) . ?
O0AA Yb1 2.317(4) 4_655 ?
O0AA C109 1.255(6) . ?
C106 C109 1.497(7) . ?
C106 C107 1.401(7) . ?
C106 C105 1.400(7) . ?
C202 Yb1 3.207(5) 5_665 ?
C202 C203 1.501(7) . ?
C205 H205 0.9500 . ?
C205 C203 1.397(7) . ?
C205 C204 1.385(7) 7_655 ?
O102 Yb1 2.257(4) 5_665 ?
C103 C104 1.394(7) . ?
C103 C108 1.400(8) . ?
O301 C302 1.242(8) . ?
C302 H302 0.9500 . ?
C302 N303 1.330(8) . ?
C104 H104 0.9500 . ?
C104 C105 1.385(7) . ?
C108 H108 0.9500 . ?
C108 C107 1.384(8) . ?
C203 C204 1.385(7) . ?
C107 H107 0.9500 . ?
C105 H105 0.9500 . ?
C204 C205 1.385(7) 7_655 ?
C204 H204 0.9500 . ?
N303 C305 1.444(9) . ?
N303 C304 1.440(10) . ?
C305 H30A 0.9800 . ?
C305 H30B 0.9800 . ?
C305 H30C 0.9800 . ?
C304 H30D 0.9800 . ?
C304 H30E 0.9800 . ?
C304 H30F 0.9800 . ?
O1 H1A 0.8696 . ?
O1 H1B 0.8700 . ?

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
O201 Yb1 Yb1 56.23(10) . 5_665 ?
O201 Yb1 O202 126.56(14) . 5_665 ?
O201 Yb1 O101 79.59(15) . . ?
O201 Yb1 O0AA 79.26(13) . 4_645 ?
O201 Yb1 C202 108.71(13) . 5_665 ?
O201 Yb1 O102 80.30(14) . 5_665 ?
O201 Yb1 O301 81.89(14) . . ?
O202 Yb1 Yb1 70.36(10) 5_665 5_665 ?
O202 Yb1 O0AA 139.64(14) 5_665 4_645 ?
O202 Yb1 C202 18.74(14) 5_665 5_665 ?
O202 Yb1 O301 132.88(15) 5_665 . ?
O101 Yb1 Yb1 66.84(10) . 5_665 ?
O101 Yb1 O202 78.37(15) . 5_665 ?
O101 Yb1 O0AA 77.05(14) . 4_645 ?
O101 Yb1 C202 77.98(13) . 5_665 ?
O101 Yb1 O102 125.09(13) . 5_665 ?
O101 Yb1 O301 148.53(15) . . ?
O110 Yb1 Yb1 143.41(10) 3_445 5_665 ?
O110 Yb1 O201 159.81(14) 3_445 . ?
O110 Yb1 O202 73.40(14) 3_445 5_665 ?
O110 Yb1 O101 110.59(13) 3_445 . ?
O110 Yb1 O0AA 86.00(14) 3_445 4_645 ?
O110 Yb1 C202 90.77(13) 3_445 5_665 ?
O110 Yb1 O102 105.56(15) 3_445 5_665 ?
O110 Yb1 O301 80.94(13) 3_445 . ?
O0AA Yb1 Yb1 125.89(9) 4_645 5_665 ?
O0AA Yb1 C202 151.84(13) 4_645 5_665 ?
O0AA Yb1 O301 74.65(14) 4_645 . ?
C202 Yb1 Yb1 52.64(9) 5_665 5_665 ?
O102 Yb1 Yb1 59.48(10) 5_665 5_665 ?
O102 Yb1 O202 74.02(15) 5_665 5_665 ?
O102 Yb1 O0AA 146.04(13) 5_665 4_645 ?
O102 Yb1 C202 61.42(13) 5_665 5_665 ?
O102 Yb1 O301 75.84(14) 5_665 . ?
O301 Yb1 Yb1 121.27(10) . 5_665 ?
O301 Yb1 C202 132.42(15) . 5_665 ?
O101 C102 C103 117.3(5) . . ?
O102 C102 O101 125.7(5) . . ?
O102 C102 C103 117.0(5) . . ?
C202 O201 Yb1 154.8(4) . . ?
C202 O202 Yb1 125.4(3) . 5_665 ?
C102 O101 Yb1 134.5(4) . . ?
C109 O110 Yb1 147.1(3) . 3 ?
C109 O0AA Yb1 130.3(3) . 4_655 ?
C107 C106 C109 121.0(5) . . ?
C105 C106 C109 119.8(5) . . ?
C105 C106 C107 119.2(5) . . ?
O201 C202 Yb1 93.4(3) . 5_665 ?
O201 C202 C203 117.7(5) . . ?
O202 C202 Yb1 35.9(2) . 5_665 ?
O202 C202 O201 124.2(5) . . ?
O202 C202 C203 118.2(5) . . ?
C203 C202 Yb1 143.2(3) . 5_665 ?
O110 C109 C106 117.6(5) . . ?
O0AA C109 O110 123.5(5) . . ?
O0AA C109 C106 118.8(5) . . ?
C203 C205 H205 120.3 . . ?
C204 C205 H205 120.3 7_655 . ?
C204 C205 C203 119.4(5) 7_655 . ?
C102 O102 Yb1 148.6(4) . 5_665 ?
C104 C103 C102 120.1(5) . . ?
C104 C103 C108 120.1(5) . . ?
C108 C103 C102 119.9(5) . . ?
C302 O301 Yb1 127.4(5) . . ?
O301 C302 H302 117.9 . . ?
O301 C302 N303 124.3(8) . . ?
N303 C302 H302 117.9 . . ?
C103 C104 H104 120.1 . . ?
C105 C104 C103 119.8(5) . . ?
C105 C104 H104 120.1 . . ?
C103 C108 H108 120.0 . . ?
C107 C108 C103 119.9(5) . . ?
C107 C108 H108 120.0 . . ?
C205 C203 C202 120.6(5) . . ?
C204 C203 C202 119.5(5) . . ?
C204 C203 C205 119.9(5) . . ?
C106 C107 H107 119.8 . . ?
C108 C107 C106 120.3(5) . . ?
C108 C107 H107 119.8 . . ?
C106 C105 H105 119.7 . . ?
C104 C105 C106 120.7(5) . . ?
C104 C105 H105 119.7 . . ?
C205 C204 C203 120.7(5) 7_655 . ?
C205 C204 H204 119.6 7_655 . ?
C203 C204 H204 119.6 . . ?
C302 N303 C305 120.9(7) . . ?
C302 N303 C304 119.6(6) . . ?
C304 N303 C305 119.4(6) . . ?
N303 C305 H30A 109.5 . . ?
N303 C305 H30B 109.5 . . ?
N303 C305 H30C 109.5 . . ?
H30A C305 H30B 109.5 . . ?
H30A C305 H30C 109.5 . . ?
H30B C305 H30C 109.5 . . ?
N303 C304 H30D 109.5 . . ?
N303 C304 H30E 109.5 . . ?
N303 C304 H30F 109.5 . . ?
H30D C304 H30E 109.5 . . ?
H30D C304 H30F 109.5 . . ?
H30E C304 H30F 109.5 . . ?
H1A O1 H1B 109.5 . . ?

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
O1 H1A O202 0.87 2.01 2.869(11) 171.7 .
O1 H1B O101 0.87 2.17 3.011(10) 161.1 6_565

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
Yb1 O201 C202 Yb1 -28.2(9) . . . 5_665 ?
Yb1 O201 C202 O202 -48.0(12) . . . . ?
Yb1 O201 C202 C203 131.3(7) . . . . ?
Yb1 O202 C202 O201 35.3(8) 5_665 . . . ?
Yb1 O202 C202 C203 -144.0(4) 5_665 . . . ?
Yb1 O110 C109 O0AA 112.0(7) 3 . . . ?
Yb1 O110 C109 C106 -68.8(8) 3 . . . ?
Yb1 O0AA C109 O110 10.2(8) 4_655 . . . ?
Yb1 O0AA C109 C106 -168.9(3) 4_655 . . . ?
Yb1 C202 C203 C205 -49.4(8) 5_665 . . . ?
Yb1 C202 C203 C204 130.2(5) 5_665 . . . ?
Yb1 O301 C302 N303 164.5(5) . . . . ?
C102 C103 C104 C105 -178.9(5) . . . . ?
C102 C103 C108 C107 178.3(5) . . . . ?
O201 C202 C203 C205 166.2(5) . . . . ?
O201 C202 C203 C204 -14.2(8) . . . . ?
O202 C202 C203 C205 -14.4(8) . . . . ?
O202 C202 C203 C204 165.2(5) . . . . ?
O101 C102 O102 Yb1 11.5(11) . . . 5_665 ?
O101 C102 C103 C104 -160.3(5) . . . . ?
O101 C102 C103 C108 20.9(8) . . . . ?
C202 C203 C204 C205 -179.8(5) . . . 7_655 ?
C109 C106 C107 C108 179.5(5) . . . . ?
C109 C106 C105 C104 179.9(5) . . . . ?
C205 C203 C204 C205 -0.2(9) . . . 7_655 ?
O102 C102 O101 Yb1 21.0(9) . . . . ?
O102 C102 C103 C104 20.7(8) . . . . ?
O102 C102 C103 C108 -158.2(5) . . . . ?
C103 C102 O101 Yb1 -158.0(4) . . . . ?
C103 C102 O102 Yb1 -169.6(5) . . . 5_665 ?
C103 C104 C105 C106 0.9(8) . . . . ?
C103 C108 C107 C106 0.4(8) . . . . ?
O301 C302 N303 C305 178.6(6) . . . . ?
O301 C302 N303 C304 1.4(11) . . . . ?
C104 C103 C108 C107 -0.5(8) . . . . ?
C108 C103 C104 C105 -0.1(8) . . . . ?
C107 C106 C109 O110 166.0(5) . . . . ?
C107 C106 C109 O0AA -14.8(8) . . . . ?
C107 C106 C105 C104 -1.1(8) . . . . ?
C105 C106 C109 O110 -15.0(7) . . . . ?
C105 C106 C109 O0AA 164.2(5) . . . . ?
C105 C106 C107 C108 0.5(8) . . . . ?
C204 C205 C203 C202 179.8(5) 7_655 . . . ?
C204 C205 C203 C204 0.2(9) 7_655 . . . ?

_shelx_SHELXL_version_number     2014/7
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
2 4 -23 0.1308 2.4801 4.1710 -23.4512 -0.1955 -0.0568 0.9791
0 15 -5 0.0396 -0.0070 14.9997 -5.0027 -0.5248 0.7469 0.4155
25 3 0 0.0576 24.5462 3.4479 0.3373 -0.9289 -0.2763 -0.2466
-5 15 -5 0.0498 -5.1034 14.5613 -4.6185 -0.3424 0.8235 0.4523
0 4 23 0.1379 0.1955 3.9028 23.1764 -0.1785 0.4322 -0.8840
-7 14 -2 0.0566 -7.0097 14.0014 -2.0011 -0.2637 0.8556 0.3604
-18 -10 -4 0.0672 -17.9990 -9.9990 -3.9935 0.9516 -0.2309 0.2261
-11 -14 2 0.0267 -10.9963 -13.9988 2.0053 0.8549 -0.5160 -0.1537
-5 -5 23 0.1280 -5.2037 -4.5487 23.3839 0.2984 0.0874 -0.9504
-11 -13 -3 0.0230 -10.9953 -12.9999 -2.9945 0.8267 -0.5123 0.0626
2 -15 -8 0.0675 2.0117 -15.0031 -7.9967 0.4779 -0.9132 0.0870
25 -1 -1 0.0955 25.0091 -1.0039 -1.0054 -0.7842 -0.5346 -0.2609
25 4 -1 0.0903 25.0063 3.9965 -1.0065 -0.9615 -0.2691 -0.1897
-25 0 -1 0.0783 -25.0079 0.0033 -0.9942 0.8226 0.4617 0.3275
-18 -11 1 0.0688 -18.0000 -10.9979 1.0063 0.9799 -0.2346 0.0098
5 -15 0 0.0171 4.9619 -14.9865 0.2163 0.3685 -0.8869 -0.2787

_olex2_submission_special_instructions 'No special instructions were received'

loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.8746(5)
2 0.1254(5)

####################################################################### 
# 
# 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_mb5
_database_code_depnum_ccdc_archive 'CCDC 1537044'
_audit_update_record             
;
2017-03-09 deposited with the CCDC.
2017-04-11 downloaded from the CCDC.
;
_audit_creation_date             2017-03-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.02.23 svn.r3390 for OlexSys, GUI svn.r5320)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C18 H13 O8 Yb, C3 H7 N O'
_chemical_formula_sum            'C21 H20 N O9 Yb'
_chemical_formula_weight         603.42
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 N2 O18P Ir'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Yb Yb -0.3850 5.5486 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   8.4515(2)
_cell_length_b                   12.3972(4)
_cell_length_c                   12.5680(3)
_cell_angle_alpha                110.453(2)
_cell_angle_beta                 102.132(2)
_cell_angle_gamma                109.619(3)
_cell_volume                     1079.19(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    13197
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      31.3520
_cell_measurement_theta_min      3.0980
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.386
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65580
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.38.43d (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.857
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             590
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
9 7 -9 0.0967
0 7 -17 0.1543
-4 -6 18 0.0689
4 -5 15 0.1295
6 -13 -7 0.0886
-5 13 7 0.0088
-9 -7 8 0.0230

_exptl_crystal_size_max          0.357
_exptl_crystal_size_mid          0.124
_exptl_crystal_size_min          0.105
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
9.0011 7.0015 -9.0019 -0.8941 -0.5037 -0.0406
0.0017 7.0003 -17.0036 -0.3140 -0.1822 0.9121
-4.0019 -6.0003 18.0031 0.4829 0.4523 -0.7824
3.9986 -4.9997 15.0033 -0.0292 -0.0281 -1.0325
6.0013 -13.0028 -6.9968 0.4733 -0.8394 0.3366
-5.0013 13.0029 6.9969 -0.5322 0.7842 -0.3885
-9.0010 -7.0016 8.0018 0.9004 0.4818 0.1013

_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0837
_diffrn_reflns_av_unetI/netI     0.0580
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.903
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            20934
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.903
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.595
_diffrn_reflns_theta_min         3.099
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2833
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.903
_diffrn_measurement_details      
'List of Runs (angles in degrees, time in seconds): # Type Start End Width tₑₓₚ ω θ κ φ Frames -------------------------------------------------------------------------- 1 ω -58.00 43.00 1.00 25.00 -- 16.32 -57.00 -60.00 101 2 ω -56.00 32.00 1.00 25.00 -- 16.32 -57.00 60.00 88 3 ω -47.00 50.00 1.00 25.00 -- -17.25 57.00-180.00 97 4 ω -91.00 12.00 1.00 25.00 -- -17.25 -57.00 30.00 103 5 ω -79.00 9.00 1.00 25.00 -- -17.25 -38.00-120.00 88 6 ω -90.00 16.00 1.00 25.00 -- -17.25 -77.00-180.00 106 7 ω -91.00 -34.00 1.00 25.00 -- -17.25 150.00-157.74 57 8 ω -80.00 -34.00 1.00 25.00 -- -17.25 133.00 -7.67 46'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0588476000
_diffrn_orient_matrix_UB_12      -0.0601649000
_diffrn_orient_matrix_UB_13      -0.0063111000
_diffrn_orient_matrix_UB_21      -0.0552321000
_diffrn_orient_matrix_UB_22      0.0272633000
_diffrn_orient_matrix_UB_23      0.0219347000
_diffrn_orient_matrix_UB_31      -0.0518766000
_diffrn_orient_matrix_UB_32      -0.0171615000
_diffrn_orient_matrix_UB_33      -0.0607112000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5870
_reflns_number_total             6549
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.98
_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       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         2.462
_refine_diff_density_min         -1.764
_refine_diff_density_rms         0.218
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         6549
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0403
_refine_ls_restrained_S_all      1.041
_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)+(0.0711P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1032
_refine_ls_wR_factor_ref         0.1065
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
All the crystals examined were twinned. The data was collected on the best crystal. 
A suitable twin refinement could not be realized so the refinement was conducted on 
the major twin component and is the data presented here.
The hydrogens on the water were located in a difference map but placed at calculated 
positions for the refinement.
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Rotating group:
 O1D(H1DA,H1DB), O1E(H1EA,H1EB)
2.b Aromatic/amide H refined with riding coordinates:
 C4A(H4A), C5A(H5A), C7A(H7A), C4B(H4B), C5B(H5B), C7B(H7B), C4C(H4C),
 C5C(H5C), C7C(H7C), C101(H101)
2.c Idealised Me refined as rotating group:
 C103(H10A,H10B,H10C), C104(H10D,H10E,H10F)
;
_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
Yb1 Yb 0.70597(2) 0.54147(2) 0.40361(2) 0.01868(7) Uani 1 1 d . . . . .
O1A O 0.8610(4) 0.7339(3) 0.3927(3) 0.0293(6) Uani 1 1 d . . . . .
O2A O 1.0282(4) 0.6717(3) 0.4932(3) 0.0258(5) Uani 1 1 d . . . . .
C2A C 1.0143(6) 0.7489(4) 0.4500(4) 0.0246(7) Uani 1 1 d . . . . .
C3A C 1.1823(5) 0.8529(4) 0.4638(4) 0.0248(7) Uani 1 1 d . . . . .
C4A C 1.1694(6) 0.9521(4) 0.4356(4) 0.0278(8) Uani 1 1 d . . . . .
H4A H 1.0551 0.9511 0.4081 0.033 Uiso 1 1 calc R . . . .
C5A C 1.3230(5) 1.0492(4) 0.4484(4) 0.0277(8) Uani 1 1 d . . . . .
H5A H 1.3149 1.1167 0.4318 0.033 Uiso 1 1 calc R . . . .
C6A C 1.4934(6) 1.0494(4) 0.4863(4) 0.0253(7) Uani 1 1 d . . . . .
C7A C 1.6534(6) 1.1466(4) 0.4969(4) 0.0269(7) Uani 1 1 d . . . . .
H7A H 1.6464 1.2122 0.4764 0.032 Uiso 1 1 calc R . . . .
O1B O 0.5503(4) 0.4915(3) 0.2010(2) 0.0271(6) Uani 1 1 d . . . . .
O2B O 0.4408(4) 0.5666(3) 0.3389(2) 0.0247(5) Uani 1 1 d . . . . .
C2B C 0.4301(5) 0.5213(4) 0.2275(3) 0.0226(7) Uani 1 1 d . . . . .
C3B C 0.2759(5) 0.5035(4) 0.1282(4) 0.0258(8) Uani 1 1 d . . . . .
C4B C 0.2617(6) 0.4449(5) 0.0057(4) 0.0314(9) Uani 1 1 d . . . . .
H4B H 0.3489 0.4167 -0.0122 0.038 Uiso 1 1 calc R . . . .
C5B C 0.1234(6) 0.4283(5) -0.0876(4) 0.0323(9) Uani 1 1 d . . . . .
H5B H 0.1149 0.3886 -0.1697 0.039 Uiso 1 1 calc R . . . .
C6B C -0.0074(5) 0.4705(4) -0.0617(3) 0.0239(7) Uani 1 1 d . . . . .
C7B C -0.1507(5) 0.4545(4) -0.1558(3) 0.0260(7) Uani 1 1 d . . . . .
H7B H -0.1614 0.4148 -0.2384 0.031 Uiso 1 1 calc R . . . .
O1C O 0.7165(4) 0.6730(3) 0.5784(3) 0.0305(6) Uani 1 1 d . . . . .
O2C O 0.5160(4) 0.6585(3) 0.6678(3) 0.0317(6) Uani 1 1 d . . . . .
C2C C 0.6715(6) 0.7086(4) 0.6685(3) 0.0234(7) Uani 1 1 d . . . . .
C3C C 0.8179(6) 0.8210(4) 0.7851(4) 0.0242(7) Uani 1 1 d . . . . .
C4C C 0.9997(7) 0.8658(5) 0.7961(4) 0.0428(12) Uani 1 1 d . . . . .
H4C H 1.0300 0.8283 0.7283 0.051 Uiso 1 1 calc R . . . .
C5C C 1.1319(6) 0.9622(5) 0.9032(4) 0.0445(12) Uani 1 1 d . . . . .
H5C H 1.2546 0.9892 0.9103 0.053 Uiso 1 1 calc R . . . .
C6C C 1.0913(6) 1.0235(4) 1.0044(4) 0.0309(9) Uani 1 1 d . . . . .
C7C C 1.2265(6) 1.1270(4) 1.1167(4) 0.0323(9) Uani 1 1 d . . . . .
H7C H 1.3492 1.1608 1.1239 0.039 Uiso 1 1 calc R . . . .
O1D O 0.8255(4) 0.4205(3) 0.2988(3) 0.0315(7) Uani 1 1 d . . . . .
H1DA H 0.9388 0.4496 0.3428 0.047 Uiso 1 1 d GR . . . .
H1DB H 0.8172 0.4250 0.2305 0.047 Uiso 1 1 d GR . . . .
O1E O 0.8045(4) 0.4763(3) 0.5504(2) 0.0224(5) Uani 1 1 d . . . . .
H1EA H 0.7301 0.4673 0.5898 0.034 Uiso 1 1 d GR . . . .
H1EB H 0.8296 0.4163 0.5178 0.034 Uiso 1 1 d GR . . . .
O100 O 0.6806(7) 0.2435(4) 0.0747(3) 0.0568(11) Uani 1 1 d . . . . .
C101 C 0.5764(9) 0.2462(5) -0.0064(5) 0.0447(12) Uani 1 1 d . . . . .
H101 H 0.5193 0.2999 0.0175 0.054 Uiso 1 1 calc R . . . .
N102 N 0.5358(8) 0.1804(5) -0.1254(4) 0.0509(12) Uani 1 1 d . . . . .
C103 C 0.4033(10) 0.1798(6) -0.2191(5) 0.0575(16) Uani 1 1 d . . . . .
H10A H 0.3533 0.2370 -0.1809 0.086 Uiso 1 1 calc GR . . . .
H10B H 0.3057 0.0922 -0.2700 0.086 Uiso 1 1 calc GR . . . .
H10C H 0.4606 0.2099 -0.2701 0.086 Uiso 1 1 calc GR . . . .
C104 C 0.6352(17) 0.1092(10) -0.1645(7) 0.107(4) Uani 1 1 d . . . A 1
H10D H 0.5548 0.0167 -0.2037 0.160 Uiso 1 1 calc GR . . A 1
H10E H 0.7366 0.1310 -0.0934 0.160 Uiso 1 1 calc GR . . A 1
H10F H 0.6816 0.1316 -0.2229 0.160 Uiso 1 1 calc GR . . A 1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Yb1 O1A 2.372(3) . ?
Yb1 O2A 2.404(3) . ?
Yb1 O1B 2.354(3) . ?
Yb1 O2B 2.379(3) . ?
Yb1 O1C 2.193(3) . ?
Yb1 O2C 2.255(3) 2_666 ?
Yb1 O1D 2.281(3) . ?
Yb1 H1DA 2.6993 . ?
Yb1 H1DB 2.6975 . ?
Yb1 O1E 2.366(3) . ?
Yb1 H1EB 2.7528 . ?
O1A C2A 1.258(5) . ?
O2A C2A 1.279(5) . ?
C2A C3A 1.490(6) . ?
C3A C4A 1.424(5) . ?
C3A C7A 1.370(5) 2_876 ?
C4A H4A 0.9500 . ?
C4A C5A 1.374(6) . ?
C5A H5A 0.9500 . ?
C5A C6A 1.418(5) . ?
C6A C6A 1.415(7) 2_876 ?
C6A C7A 1.421(6) . ?
C7A C3A 1.370(5) 2_876 ?
C7A H7A 0.9500 . ?
O1B C2B 1.260(4) . ?
O2B C2B 1.284(4) . ?
C2B C3B 1.495(5) . ?
C3B C4B 1.412(5) . ?
C3B C7B 1.382(5) 2_565 ?
C4B H4B 0.9500 . ?
C4B C5B 1.371(5) . ?
C5B H5B 0.9500 . ?
C5B C6B 1.422(5) . ?
C6B C6B 1.420(7) 2_565 ?
C6B C7B 1.406(5) . ?
C7B C3B 1.382(5) 2_565 ?
C7B H7B 0.9500 . ?
O1C C2C 1.252(5) . ?
O2C Yb1 2.255(3) 2_666 ?
O2C C2C 1.247(5) . ?
C2C C3C 1.508(5) . ?
C3C C4C 1.404(6) . ?
C3C C7C 1.371(5) 2_777 ?
C4C H4C 0.9500 . ?
C4C C5C 1.354(6) . ?
C5C H5C 0.9500 . ?
C5C C6C 1.414(6) . ?
C6C C6C 1.418(8) 2_777 ?
C6C C7C 1.420(6) . ?
C7C C3C 1.371(5) 2_777 ?
C7C H7C 0.9500 . ?
O1D H1DA 0.8713 . ?
O1D H1DB 0.8700 . ?
O1E H1EA 0.8795 . ?
O1E H1EB 0.8348 . ?
O100 C101 1.218(6) . ?
C101 H101 0.9500 . ?
C101 N102 1.329(6) . ?
N102 C103 1.441(8) . ?
N102 C104 1.447(9) . ?
C103 H10A 0.9800 . ?
C103 H10B 0.9800 . ?
C103 H10C 0.9800 . ?
C104 H10D 0.9800 . ?
C104 H10E 0.9800 . ?
C104 H10F 0.9800 . ?

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
O1A Yb1 O2A 54.88(9) . . ?
O1A Yb1 O2B 85.65(10) . . ?
O1A Yb1 H1DA 92.3 . . ?
O1A Yb1 H1DB 87.0 . . ?
O1A Yb1 H1EB 131.4 . . ?
O2A Yb1 H1DA 57.5 . . ?
O2A Yb1 H1DB 77.5 . . ?
O2A Yb1 H1EB 76.5 . . ?
O1B Yb1 O1A 77.29(11) . . ?
O1B Yb1 O2A 118.74(10) . . ?
O1B Yb1 O2B 55.48(9) . . ?
O1B Yb1 H1DA 93.3 . . ?
O1B Yb1 H1DB 62.8 . . ?
O1B Yb1 O1E 150.36(10) . . ?
O1B Yb1 H1EB 135.9 . . ?
O2B Yb1 O2A 138.05(10) . . ?
O2B Yb1 H1DA 148.4 . . ?
O2B Yb1 H1DB 118.0 . . ?
O2B Yb1 H1EB 139.9 . . ?
O1C Yb1 O1A 83.81(12) . . ?
O1C Yb1 O2A 82.92(11) . . ?
O1C Yb1 O1B 131.21(10) . . ?
O1C Yb1 O2B 78.79(10) . . ?
O1C Yb1 O2C 111.11(12) . 2_666 ?
O1C Yb1 O1D 149.22(11) . . ?
O1C Yb1 H1DA 132.4 . . ?
O1C Yb1 H1DB 160.2 . . ?
O1C Yb1 O1E 72.86(10) . . ?
O1C Yb1 H1EB 89.5 . . ?
O2C Yb1 O1A 154.60(12) 2_666 . ?
O2C Yb1 O2A 144.24(10) 2_666 . ?
O2C Yb1 O1B 77.48(11) 2_666 . ?
O2C Yb1 O2B 77.71(11) 2_666 . ?
O2C Yb1 O1D 79.22(12) 2_666 . ?
O2C Yb1 H1DA 92.0 2_666 . ?
O2C Yb1 H1DB 84.1 2_666 . ?
O2C Yb1 O1E 77.00(10) 2_666 . ?
O2C Yb1 H1EB 71.1 2_666 . ?
O1D Yb1 O1A 98.57(12) . . ?
O1D Yb1 O2A 73.93(10) . . ?
O1D Yb1 O1B 78.64(10) . . ?
O1D Yb1 O2B 131.93(10) . . ?
O1D Yb1 H1DA 17.7 . . ?
O1D Yb1 H1DB 17.7 . . ?
O1D Yb1 O1E 82.00(10) . . ?
O1D Yb1 H1EB 65.8 . . ?
H1DA Yb1 H1DB 30.6 . . ?
H1DA Yb1 H1EB 58.5 . . ?
H1DB Yb1 H1EB 83.5 . . ?
O1E Yb1 O1A 128.06(10) . . ?
O1E Yb1 O2A 76.26(9) . . ?
O1E Yb1 O2B 131.51(9) . . ?
O1E Yb1 H1DA 72.8 . . ?
O1E Yb1 H1DB 99.7 . . ?
O1E Yb1 H1EB 16.7 . . ?
C2A O1A Yb1 93.3(2) . . ?
C2A O2A Yb1 91.3(2) . . ?
O1A C2A O2A 120.3(4) . . ?
O1A C2A C3A 120.7(4) . . ?
O2A C2A C3A 118.8(4) . . ?
C4A C3A C2A 118.9(4) . . ?
C7A C3A C2A 120.6(4) 2_876 . ?
C7A C3A C4A 120.5(4) 2_876 . ?
C3A C4A H4A 120.1 . . ?
C5A C4A C3A 119.7(4) . . ?
C5A C4A H4A 120.1 . . ?
C4A C5A H5A 119.8 . . ?
C4A C5A C6A 120.4(4) . . ?
C6A C5A H5A 119.8 . . ?
C5A C6A C7A 121.5(4) . . ?
C6A C6A C5A 120.0(5) 2_876 . ?
C6A C6A C7A 118.5(5) 2_876 . ?
C3A C7A C6A 120.8(4) 2_876 . ?
C3A C7A H7A 119.6 2_876 . ?
C6A C7A H7A 119.6 . . ?
C2B O1B Yb1 93.1(2) . . ?
C2B O2B Yb1 91.3(2) . . ?
O1B C2B O2B 120.0(3) . . ?
O1B C2B C3B 119.4(3) . . ?
O2B C2B C3B 120.6(3) . . ?
C4B C3B C2B 119.0(3) . . ?
C7B C3B C2B 120.6(4) 2_565 . ?
C7B C3B C4B 120.4(4) 2_565 . ?
C3B C4B H4B 119.7 . . ?
C5B C4B C3B 120.6(4) . . ?
C5B C4B H4B 119.7 . . ?
C4B C5B H5B 120.0 . . ?
C4B C5B C6B 120.1(4) . . ?
C6B C5B H5B 120.0 . . ?
C6B C6B C5B 119.1(4) 2_565 . ?
C7B C6B C5B 121.2(3) . . ?
C7B C6B C6B 119.7(4) . 2_565 ?
C3B C7B C6B 120.1(4) 2_565 . ?
C3B C7B H7B 120.0 2_565 . ?
C6B C7B H7B 120.0 . . ?
C2C O1C Yb1 157.7(3) . . ?
C2C O2C Yb1 137.5(3) . 2_666 ?
O1C C2C C3C 116.5(4) . . ?
O2C C2C O1C 124.7(4) . . ?
O2C C2C C3C 118.7(4) . . ?
C4C C3C C2C 120.3(4) . . ?
C7C C3C C2C 119.3(4) 2_777 . ?
C7C C3C C4C 120.2(4) 2_777 . ?
C3C C4C H4C 119.9 . . ?
C5C C4C C3C 120.2(4) . . ?
C5C C4C H4C 119.9 . . ?
C4C C5C H5C 119.3 . . ?
C4C C5C C6C 121.4(4) . . ?
C6C C5C H5C 119.3 . . ?
C5C C6C C6C 118.8(5) . 2_777 ?
C5C C6C C7C 122.8(4) . . ?
C6C C6C C7C 118.4(5) 2_777 . ?
C3C C7C C6C 120.8(4) 2_777 . ?
C3C C7C H7C 119.6 2_777 . ?
C6C C7C H7C 119.6 . . ?
Yb1 O1D H1DA 109.5 . . ?
Yb1 O1D H1DB 109.4 . . ?
H1DA O1D H1DB 109.5 . . ?
Yb1 O1E H1EA 109.9 . . ?
Yb1 O1E H1EB 108.9 . . ?
H1EA O1E H1EB 120.0 . . ?
O100 C101 H101 117.3 . . ?
O100 C101 N102 125.4(5) . . ?
N102 C101 H101 117.3 . . ?
C101 N102 C103 123.9(5) . . ?
C101 N102 C104 118.7(5) . . ?
C103 N102 C104 117.4(5) . . ?
N102 C103 H10A 109.5 . . ?
N102 C103 H10B 109.5 . . ?
N102 C103 H10C 109.5 . . ?
H10A C103 H10B 109.5 . . ?
H10A C103 H10C 109.5 . . ?
H10B C103 H10C 109.5 . . ?
N102 C104 H10D 109.5 . . ?
N102 C104 H10E 109.5 . . ?
N102 C104 H10F 109.5 . . ?
H10D C104 H10E 109.5 . . ?
H10D C104 H10F 109.5 . . ?
H10E C104 H10F 109.5 . . ?

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
O1D H1DA O1E 0.87 1.98 2.852(4) 176.8 2_766
O1D H1DB O100 0.87 2.11 2.584(5) 113.4 .
O1E H1EA O2B 0.88 1.86 2.739(4) 174.7 2_666
O1E H1EB O2A 0.83 1.87 2.652(4) 155.4 2_766

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
'Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling'
_oxdiff_exptl_absorpt_empirical_full_max 1.476
_oxdiff_exptl_absorpt_empirical_full_min 0.724
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               3
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.7738 16658 5221 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000 0.0000
1.0000
2 0.1899 16666 5243 nmt 1.0102 0.0179 0.0024 -0.0203 1.0054 0.0298 -0.0145
-0.0412 0.9840
3 0.0362 17062 4967 nmt 0.9983 0.0211 -0.0246 -0.0451 1.0081 0.0562 0.0545
-0.0521 0.9857

_twin_special_details            
'Component 2 rotated by 2.1977° around [-0.69 0.47 -0.55] (reciprocal) or [-0.90 -0.14 -0.42] (direct) Component 3 rotated by 4.2318° around [-0.67 -0.59 -0.46] (reciprocal) or [-0.77 -0.49 -0.40] (direct)'
