# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_X
_database_code_depnum_ccdc_archive 'CCDC 1414831'
_audit_update_record             
;
2016-02-25 deposited with the CCDC.
2016-03-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H44 N12 O18 Pr2, 2(Cl O4)'
_chemical_formula_sum            'C36 H44 Cl2 N12 O26 Pr2'
_chemical_formula_weight         1413.55

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pr Pr -0.2180 2.8214 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   6.8160(14)
_cell_length_b                   17.247(3)
_cell_length_c                   27.329(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.03(3)
_cell_angle_gamma                90
_cell_volume                     3212.2(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5897
_cell_measurement_theta_min      1.396
_cell_measurement_theta_max      25.368

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_F_000             1408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.661
_shelx_estimated_absorpt_T_min   0.730
_shelx_estimated_absorpt_T_max   0.850
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5897
_diffrn_reflns_av_unetI/netI     0.0878
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         1.396
_diffrn_reflns_theta_max         25.368
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5897
_reflns_number_gt                3874
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       block
_computing_cell_refinement       green
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0859P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5897
_refine_ls_number_parameters     358
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0935
_refine_ls_R_factor_gt           0.0573
_refine_ls_wR_factor_ref         0.1535
_refine_ls_wR_factor_gt          0.1381
_refine_ls_goodness_of_fit_ref   0.963
_refine_ls_restrained_S_all      0.962
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Pr Pr 0.53232(6) 0.64094(2) 0.04211(2) 0.02918(15) Uani 1 1 d . . . . .
O1 O 0.4531(9) 0.6084(4) -0.04100(18) 0.0457(15) Uani 1 1 d . . . . .
N1 N 0.4782(9) 0.6620(4) -0.2719(2) 0.0329(15) Uani 1 1 d . . . . .
C1 C 0.4213(11) 0.5594(4) -0.0739(3) 0.0288(16) Uani 1 1 d . . . . .
O2 O 0.4817(9) 0.7540(3) 0.10540(19) 0.0409(14) Uani 1 1 d . . . . .
C2 C 0.4377(10) 0.5858(4) -0.1254(2) 0.0271(16) Uani 1 1 d . . . . .
N2 N 0.5038(12) 0.6594(5) -0.3515(3) 0.057(2) Uani 1 1 d . . . . .
O3 O 0.3874(9) 0.6376(3) 0.12632(18) 0.0421(14) Uani 1 1 d . . . . .
N3 N 0.4543(10) 0.7343(5) -0.3367(3) 0.049(2) Uani 1 1 d . . . . .
C3 C 0.4173(12) 0.5333(5) -0.1647(3) 0.0336(18) Uani 1 1 d . . . . .
H3B H 0.3953 0.4811 -0.1582 0.040 Uiso 1 1 calc R U . . .
N4 N 0.4959(10) 0.7829(5) 0.3406(2) 0.0441(18) Uani 1 1 d . . . . .
C4 C 0.4293(13) 0.5580(5) -0.2123(3) 0.039(2) Uani 1 1 d . . . . .
H4A H 0.4110 0.5232 -0.2380 0.047 Uiso 1 1 calc R U . . .
O4 O 0.6946(10) 0.7557(4) 0.0050(2) 0.0597(18) Uani 1 1 d . . . . .
H4C H 0.6136 0.7931 0.0036 0.072 Uiso 1 1 d R U . . .
H4B H 0.7932 0.7685 0.0227 0.072 Uiso 1 1 d R U . . .
C5 C 0.4689(10) 0.6350(5) -0.2216(3) 0.0319(17) Uani 1 1 d . . . . .
O5 O 0.2561(9) 0.7247(4) 0.0130(2) 0.0566(18) Uani 1 1 d . . . . .
H5A H 0.1953 0.7525 0.0334 0.068 Uiso 1 1 d R U . . .
H5B H 0.2227 0.7255 -0.0171 0.068 Uiso 1 1 d R U . . .
N5 N 0.4786(12) 0.8452(5) 0.4095(3) 0.057(2) Uani 1 1 d . . . . .
O6 O 0.8259(9) 0.6511(4) 0.0983(2) 0.0531(17) Uani 1 1 d . . . . .
H6A H 0.8133 0.6697 0.1268 0.064 Uiso 1 1 d R U . . .
H6B H 0.9377 0.6361 0.0888 0.064 Uiso 1 1 d R U . . .
N6 N 0.5607(14) 0.7716(5) 0.4188(3) 0.065(2) Uani 1 1 d . . . . .
C6 C 0.4908(12) 0.6886(5) -0.1839(3) 0.041(2) Uani 1 1 d . . . . .
H6C H 0.5167 0.7404 -0.1907 0.049 Uiso 1 1 calc R U . . .
C7 C 0.4734(11) 0.6636(5) -0.1361(3) 0.0336(18) Uani 1 1 d . . . . .
H7A H 0.4858 0.6992 -0.1106 0.040 Uiso 1 1 calc R U . . .
O7 O 0.2116(9) 0.5529(4) 0.0441(2) 0.0446(15) Uani 1 1 d D . . . .
O8 O 0.6194(8) 0.5107(3) 0.06626(19) 0.0399(14) Uani 1 1 d . . . . .
C8 C 0.5141(14) 0.6162(6) -0.3126(3) 0.051(2) Uani 1 1 d . . . . .
H8A H 0.5411 0.5633 -0.3121 0.061 Uiso 1 1 calc R U . . .
O9 O 0.8454(8) 0.5948(3) -0.00235(18) 0.0373(13) Uani 1 1 d . . . . .
H9A H 0.9573 0.5977 0.0118 0.045 Uiso 1 1 d R U . . .
H9C H 0.8354 0.5768 -0.0313 0.045 Uiso 1 1 d R U . . .
C9 C 0.4416(13) 0.7331(5) -0.2900(3) 0.045(2) Uani 1 1 d . . . . .
H9B H 0.4108 0.7760 -0.2710 0.054 Uiso 1 1 calc R U . . .
C10 C 0.4338(12) 0.7072(5) 0.1379(3) 0.0366(19) Uani 1 1 d . . . . .
C11 C 0.4435(11) 0.7291(5) 0.1911(3) 0.0332(18) Uani 1 1 d . . . . .
C12 C 0.4683(11) 0.8050(5) 0.2057(3) 0.0354(18) Uani 1 1 d . . . . .
H12A H 0.4754 0.8439 0.1822 0.043 Uiso 1 1 calc R U . . .
C13 C 0.4827(12) 0.8240(5) 0.2544(3) 0.0359(18) Uani 1 1 d . . . . .
H13A H 0.4956 0.8754 0.2642 0.043 Uiso 1 1 calc R U . . .
C14 C 0.4776(12) 0.7644(5) 0.2893(3) 0.039(2) Uani 1 1 d . . . . .
C15 C 0.4500(14) 0.6883(5) 0.2750(3) 0.048(2) Uani 1 1 d . . . . .
H15A H 0.4427 0.6495 0.2986 0.058 Uiso 1 1 calc R U . . .
C16 C 0.4332(14) 0.6696(5) 0.2266(3) 0.047(2) Uani 1 1 d . . . . .
H16A H 0.4152 0.6183 0.2170 0.057 Uiso 1 1 calc R U . . .
C17 C 0.4493(12) 0.8488(6) 0.3639(3) 0.046(2) Uani 1 1 d . . . . .
H17A H 0.4005 0.8926 0.3480 0.055 Uiso 1 1 calc R U . . .
C18 C 0.5678(16) 0.7374(6) 0.3769(3) 0.063(3) Uani 1 1 d . . . . .
H18A H 0.6163 0.6876 0.3723 0.075 Uiso 1 1 calc R U . . .
Cl Cl 0.5181(6) 0.05220(19) 0.20841(14) 0.0852(10) Uani 1 1 d . . . . .
O10 O 0.345(2) 0.0195(8) 0.2166(8) 0.226(9) Uani 1 1 d . . . . .
O11 O 0.586(2) 0.0783(8) 0.2559(5) 0.166(5) Uani 1 1 d . . . . .
O12 O 0.502(2) 0.1184(7) 0.1827(5) 0.174(6) Uani 1 1 d . . . . .
O13 O 0.6491(19) -0.0008(7) 0.1895(4) 0.140(5) Uani 1 1 d . . . . .
H7C H 0.17(2) 0.528(7) 0.069(3) 0.168 Uiso 1 1 d D U . . .
H7B H 0.25(2) 0.598(4) 0.052(5) 0.168 Uiso 1 1 d D U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Pr O1 2.392(5) . ?
Pr O8 2.412(6) . ?
Pr O5 2.492(6) . ?
Pr O4 2.492(6) . ?
Pr O6 2.506(6) . ?
Pr O3 2.521(5) . ?
Pr O9 2.600(5) . ?
Pr O2 2.633(6) . ?
Pr O7 2.663(6) . ?
Pr C10 2.945(7) . ?
Pr H7B 2.08(13) . ?
O1 C1 1.249(9) . ?
N1 C9 1.345(10) . ?
N1 C8 1.391(11) . ?
N1 C5 1.454(8) . ?
C1 O8 1.259(9) 3_665 ?
C1 C2 1.487(9) . ?
O2 C10 1.247(10) . ?
C2 C7 1.395(11) . ?
C2 C3 1.409(10) . ?
N2 C8 1.297(11) . ?
N2 N3 1.397(11) . ?
O3 C10 1.279(10) . ?
N3 C9 1.281(10) . ?
C3 C4 1.373(10) . ?
C3 H3B 0.9300 . ?
N4 C17 1.343(11) . ?
N4 C18 1.351(12) . ?
N4 C14 1.440(9) . ?
C4 C5 1.381(11) . ?
C4 H4A 0.9300 . ?
O4 H4C 0.8499 . ?
O4 H4B 0.8504 . ?
C5 C6 1.390(11) . ?
O5 H5A 0.8500 . ?
O5 H5B 0.8500 . ?
N5 C17 1.262(11) . ?
N5 N6 1.408(12) . ?
O6 H6A 0.8501 . ?
O6 H6B 0.8500 . ?
N6 C18 1.290(11) . ?
C6 C7 1.383(11) . ?
C6 H6C 0.9300 . ?
C7 H7A 0.9300 . ?
O7 H7C 0.85(2) . ?
O7 H7B 0.85(2) . ?
O8 C1 1.259(9) 3_665 ?
C8 H8A 0.9300 . ?
O9 H9A 0.8498 . ?
O9 H9C 0.8504 . ?
C9 H9B 0.9300 . ?
C10 C11 1.503(10) . ?
C11 C12 1.379(11) . ?
C11 C16 1.415(12) . ?
C12 C13 1.374(10) . ?
C12 H12A 0.9300 . ?
C13 C14 1.403(12) . ?
C13 H13A 0.9300 . ?
C14 C15 1.381(12) . ?
C15 C16 1.365(11) . ?
C15 H15A 0.9300 . ?
C16 H16A 0.9300 . ?
C17 H17A 0.9300 . ?
C18 H18A 0.9300 . ?
Cl O10 1.329(13) . ?
Cl O12 1.344(12) . ?
Cl O13 1.384(10) . ?
Cl O11 1.443(12) . ?

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 Pr O8 95.25(19) . . ?
O1 Pr O5 71.1(2) . . ?
O8 Pr O5 143.9(2) . . ?
O1 Pr O4 83.9(2) . . ?
O8 Pr O4 137.9(2) . . ?
O5 Pr O4 75.4(2) . . ?
O1 Pr O6 139.6(2) . . ?
O8 Pr O6 73.0(2) . . ?
O5 Pr O6 138.2(2) . . ?
O4 Pr O6 80.7(2) . . ?
O1 Pr O3 140.9(2) . . ?
O8 Pr O3 80.08(18) . . ?
O5 Pr O3 89.9(2) . . ?
O4 Pr O3 125.0(2) . . ?
O6 Pr O3 76.4(2) . . ?
O1 Pr O9 69.96(19) . . ?
O8 Pr O9 69.06(17) . . ?
O5 Pr O9 130.57(18) . . ?
O4 Pr O9 71.3(2) . . ?
O6 Pr O9 69.79(18) . . ?
O3 Pr O9 139.29(18) . . ?
O1 Pr O2 140.14(19) . . ?
O8 Pr O2 122.96(17) . . ?
O5 Pr O2 70.94(18) . . ?
O4 Pr O2 75.1(2) . . ?
O6 Pr O2 70.02(18) . . ?
O3 Pr O2 50.13(18) . . ?
O9 Pr O2 130.71(18) . . ?
O1 Pr O7 73.39(19) . . ?
O8 Pr O7 70.20(19) . . ?
O5 Pr O7 73.8(2) . . ?
O4 Pr O7 146.3(2) . . ?
O6 Pr O7 132.4(2) . . ?
O3 Pr O7 68.49(18) . . ?
O9 Pr O7 121.05(18) . . ?
O2 Pr O7 106.96(18) . . ?
O1 Pr C10 152.1(2) . . ?
O8 Pr C10 100.2(2) . . ?
O5 Pr C10 82.8(2) . . ?
O4 Pr C10 99.4(2) . . ?
O6 Pr C10 67.7(2) . . ?
O3 Pr C10 25.6(2) . . ?
O9 Pr C10 137.45(19) . . ?
O2 Pr C10 25.0(2) . . ?
O7 Pr C10 90.2(2) . . ?
O1 Pr H7B 81(4) . . ?
O8 Pr H7B 82(2) . . ?
O5 Pr H7B 64(3) . . ?
O4 Pr H7B 139(3) . . ?
O6 Pr H7B 132(4) . . ?
O3 Pr H7B 60(3) . . ?
O9 Pr H7B 136(2) . . ?
O2 Pr H7B 94(2) . . ?
O7 Pr H7B 15(3) . . ?
C10 Pr H7B 78(3) . . ?
C1 O1 Pr 151.0(5) . . ?
C9 N1 C8 104.9(7) . . ?
C9 N1 C5 129.0(7) . . ?
C8 N1 C5 126.0(7) . . ?
O1 C1 O8 124.5(7) . 3_665 ?
O1 C1 C2 117.3(7) . . ?
O8 C1 C2 118.1(7) 3_665 . ?
C10 O2 Pr 91.6(5) . . ?
C7 C2 C3 118.4(6) . . ?
C7 C2 C1 120.6(7) . . ?
C3 C2 C1 121.0(7) . . ?
C8 N2 N3 107.7(7) . . ?
C10 O3 Pr 96.0(4) . . ?
C9 N3 N2 107.1(7) . . ?
C4 C3 C2 121.0(7) . . ?
C4 C3 H3B 119.5 . . ?
C2 C3 H3B 119.5 . . ?
C17 N4 C18 103.3(7) . . ?
C17 N4 C14 129.1(8) . . ?
C18 N4 C14 127.6(8) . . ?
C3 C4 C5 119.2(7) . . ?
C3 C4 H4A 120.4 . . ?
C5 C4 H4A 120.4 . . ?
Pr O4 H4C 109.2 . . ?
Pr O4 H4B 109.1 . . ?
H4C O4 H4B 109.5 . . ?
C4 C5 C6 121.5(7) . . ?
C4 C5 N1 119.6(7) . . ?
C6 C5 N1 118.8(7) . . ?
Pr O5 H5A 119.5 . . ?
Pr O5 H5B 120.5 . . ?
H5A O5 H5B 120.0 . . ?
C17 N5 N6 106.2(8) . . ?
Pr O6 H6A 119.8 . . ?
Pr O6 H6B 120.2 . . ?
H6A O6 H6B 120.0 . . ?
C18 N6 N5 105.9(8) . . ?
C7 C6 C5 118.9(7) . . ?
C7 C6 H6C 120.6 . . ?
C5 C6 H6C 120.6 . . ?
C6 C7 C2 121.0(7) . . ?
C6 C7 H7A 119.5 . . ?
C2 C7 H7A 119.5 . . ?
Pr O7 H7C 124(10) . . ?
Pr O7 H7B 40(9) . . ?
H7C O7 H7B 111(4) . . ?
C1 O8 Pr 152.4(5) 3_665 . ?
N2 C8 N1 108.7(8) . . ?
N2 C8 H8A 125.6 . . ?
N1 C8 H8A 125.6 . . ?
Pr O9 H9A 120.5 . . ?
Pr O9 H9C 119.6 . . ?
H9A O9 H9C 120.0 . . ?
N3 C9 N1 111.5(9) . . ?
N3 C9 H9B 124.3 . . ?
N1 C9 H9B 124.3 . . ?
O2 C10 O3 119.8(7) . . ?
O2 C10 C11 121.3(8) . . ?
O3 C10 C11 118.7(7) . . ?
O2 C10 Pr 63.3(4) . . ?
O3 C10 Pr 58.4(4) . . ?
C11 C10 Pr 162.0(5) . . ?
C12 C11 C16 119.9(7) . . ?
C12 C11 C10 121.4(8) . . ?
C16 C11 C10 118.7(7) . . ?
C13 C12 C11 120.8(8) . . ?
C13 C12 H12A 119.6 . . ?
C11 C12 H12A 119.6 . . ?
C12 C13 C14 118.9(8) . . ?
C12 C13 H13A 120.6 . . ?
C14 C13 H13A 120.6 . . ?
C15 C14 C13 120.5(7) . . ?
C15 C14 N4 119.7(8) . . ?
C13 C14 N4 119.7(7) . . ?
C16 C15 C14 120.5(8) . . ?
C16 C15 H15A 119.7 . . ?
C14 C15 H15A 119.7 . . ?
C15 C16 C11 119.2(8) . . ?
C15 C16 H16A 120.4 . . ?
C11 C16 H16A 120.4 . . ?
N5 C17 N4 113.1(9) . . ?
N5 C17 H17A 123.5 . . ?
N4 C17 H17A 123.5 . . ?
N6 C18 N4 111.6(10) . . ?
N6 C18 H18A 124.2 . . ?
N4 C18 H18A 124.2 . . ?
O10 Cl O12 112.6(11) . . ?
O10 Cl O13 111.3(9) . . ?
O12 Cl O13 114.4(8) . . ?
O10 Cl O11 104.5(11) . . ?
O12 Cl O11 103.1(9) . . ?
O13 Cl O11 110.1(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
Pr O1 C1 O8 17.6(17) . . . 3_665 ?
Pr O1 C1 C2 -160.9(8) . . . . ?
O1 C1 C2 C7 -4.4(11) . . . . ?
O8 C1 C2 C7 177.0(7) 3_665 . . . ?
O1 C1 C2 C3 175.7(7) . . . . ?
O8 C1 C2 C3 -2.9(11) 3_665 . . . ?
C8 N2 N3 C9 1.4(10) . . . . ?
C7 C2 C3 C4 -0.9(12) . . . . ?
C1 C2 C3 C4 178.9(7) . . . . ?
C2 C3 C4 C5 2.3(13) . . . . ?
C3 C4 C5 C6 -2.0(13) . . . . ?
C3 C4 C5 N1 -178.8(7) . . . . ?
C9 N1 C5 C4 152.5(8) . . . . ?
C8 N1 C5 C4 -22.2(12) . . . . ?
C9 N1 C5 C6 -24.4(12) . . . . ?
C8 N1 C5 C6 160.9(8) . . . . ?
C17 N5 N6 C18 -1.6(11) . . . . ?
C4 C5 C6 C7 0.4(12) . . . . ?
N1 C5 C6 C7 177.2(7) . . . . ?
C5 C6 C7 C2 1.0(12) . . . . ?
C3 C2 C7 C6 -0.8(11) . . . . ?
C1 C2 C7 C6 179.4(7) . . . . ?
N3 N2 C8 N1 -1.9(10) . . . . ?
C9 N1 C8 N2 1.7(10) . . . . ?
C5 N1 C8 N2 177.5(7) . . . . ?
N2 N3 C9 N1 -0.3(10) . . . . ?
C8 N1 C9 N3 -0.8(10) . . . . ?
C5 N1 C9 N3 -176.4(7) . . . . ?
Pr O2 C10 O3 -15.4(8) . . . . ?
Pr O2 C10 C11 160.0(6) . . . . ?
Pr O3 C10 O2 16.2(8) . . . . ?
Pr O3 C10 C11 -159.4(6) . . . . ?
O2 C10 C11 C12 12.8(12) . . . . ?
O3 C10 C11 C12 -171.8(7) . . . . ?
Pr C10 C11 C12 112.6(19) . . . . ?
O2 C10 C11 C16 -165.1(8) . . . . ?
O3 C10 C11 C16 10.3(11) . . . . ?
Pr C10 C11 C16 -65(2) . . . . ?
C16 C11 C12 C13 -0.2(12) . . . . ?
C10 C11 C12 C13 -178.1(7) . . . . ?
C11 C12 C13 C14 1.9(12) . . . . ?
C12 C13 C14 C15 -2.8(13) . . . . ?
C12 C13 C14 N4 178.9(7) . . . . ?
C17 N4 C14 C15 -151.7(9) . . . . ?
C18 N4 C14 C15 29.3(14) . . . . ?
C17 N4 C14 C13 26.7(13) . . . . ?
C18 N4 C14 C13 -152.4(9) . . . . ?
C13 C14 C15 C16 2.0(14) . . . . ?
N4 C14 C15 C16 -179.7(8) . . . . ?
C14 C15 C16 C11 -0.3(14) . . . . ?
C12 C11 C16 C15 -0.6(13) . . . . ?
C10 C11 C16 C15 177.3(8) . . . . ?
N6 N5 C17 N4 2.7(11) . . . . ?
C18 N4 C17 N5 -2.7(11) . . . . ?
C14 N4 C17 N5 178.0(8) . . . . ?
N5 N6 C18 N4 -0.1(12) . . . . ?
C17 N4 C18 N6 1.6(12) . . . . ?
C14 N4 C18 N6 -179.1(9) . . . . ?

_refine_diff_density_max         1.385
_refine_diff_density_min         -0.869
_refine_diff_density_rms         0.147


# SQUEEZE RESULTS (Version = 201115)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.029 0.000 0.000 336 70 ' '
2 -0.026 0.500 0.500 336 70 ' '
3 0.100 0.531 0.162 12 8 ' '
4 0.400 0.031 0.338 12 8 ' '
5 0.600 0.969 0.662 12 8 ' '
6 0.900 0.469 0.838 12 8 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          ?

# start Validation Reply Form
_vrf_PLAT420_X                   
;
PROBLEM: D-H Without Acceptor       O4     --  H4B    ...     Please Check 
RESPONSE: There are large amount of disorder water molecules in this crystal structure, some of these molecules are taken out with the squeeze restraint and give rise to the hydrogen riding on O atoms have no acceptor.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_X
_database_code_depnum_ccdc_archive 'CCDC 1414832'
_audit_update_record             
;
2016-02-25 deposited with the CCDC.
2016-03-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H17 Er N6 O7, 2(H2 O)'
_chemical_formula_sum            'C18 H21 Er N6 O9'
_chemical_formula_weight         632.67

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -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                   21.171(4)
_cell_length_b                   14.704(3)
_cell_length_c                   10.024(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.03(3)
_cell_angle_gamma                90
_cell_volume                     3103.2(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2870
_cell_measurement_theta_min      1.689
_cell_measurement_theta_max      25.409

_exptl_crystal_description       block
_exptl_crystal_colour            rufous
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_F_000             1244
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    2.749
_shelx_estimated_absorpt_T_min   0.410
_shelx_estimated_absorpt_T_max   0.613
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2870
_diffrn_reflns_av_unetI/netI     0.1392
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_theta_min         1.689
_diffrn_reflns_theta_max         25.409
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2870
_reflns_number_gt                1952
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1287P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0008(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2835
_refine_ls_number_parameters     164
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1321
_refine_ls_R_factor_gt           0.0827
_refine_ls_wR_factor_ref         0.2108
_refine_ls_wR_factor_gt          0.1877
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_restrained_S_all      0.989
_refine_ls_shift/su_max          0.082
_refine_ls_shift/su_mean         0.004

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
Er Er 0.5000 0.51734(6) 0.2500 0.0316(4) Uani 1 2 d S T P . .
O1 O 0.4107(4) 0.4743(6) 0.3470(8) 0.038(2) Uani 1 1 d . . . . .
C1 C 0.3966(5) 0.4625(8) 0.4633(10) 0.025(3) Uani 1 1 d . . . . .
N1 N 0.1496(5) 0.3190(8) 0.5113(12) 0.048(3) Uani 1 1 d . . . . .
O2 O 0.4590(5) 0.6502(7) 0.3436(10) 0.054(3) Uani 1 1 d . . . . .
H2A H 0.4330 0.6456 0.4024 0.065 Uiso 1 1 d R U . . .
H2B H 0.4702 0.7024 0.3183 0.065 Uiso 1 1 d R U . . .
C2 C 0.3309(6) 0.4269(9) 0.4731(11) 0.033(3) Uani 1 1 d . . . . .
N2 N 0.0695(6) 0.2540(9) 0.5993(12) 0.057(4) Uani 1 1 d . . . . .
O3 O 0.5686(5) 0.5245(7) 0.4309(9) 0.050(3) Uani 1 1 d . . . . .
N3 N 0.0556(6) 0.2559(10) 0.4638(13) 0.061(4) Uani 1 1 d . . . . .
C3 C 0.3074(7) 0.4150(10) 0.6013(11) 0.045(4) Uani 1 1 d . . . . .
H3C H 0.3332 0.4311 0.6785 0.054 Uiso 1 1 calc R U . . .
O4 O 0.5000 0.3591(10) 0.2500 0.052(4) Uani 1 2 d S T P . .
H4A H 0.5232 0.3405 0.1954 0.079 Uiso 0.5 1 calc R U P . .
C4 C 0.2492(7) 0.3812(11) 0.6129(14) 0.051(4) Uani 1 1 d . . . . .
H4B H 0.2348 0.3750 0.6970 0.062 Uiso 1 1 calc R U . . .
C5 C 0.2128(6) 0.3570(10) 0.5037(13) 0.041(3) Uani 1 1 d . . . . .
C6 C 0.2298(7) 0.3693(11) 0.3741(13) 0.053(4) Uani 1 1 d . . . . .
H6A H 0.2023 0.3541 0.2987 0.064 Uiso 1 1 calc R U . . .
C7 C 0.2899(7) 0.4053(10) 0.3633(11) 0.047(4) Uani 1 1 d . . . . .
H7A H 0.3025 0.4151 0.2784 0.056 Uiso 1 1 calc R U . . .
C8 C 0.1258(7) 0.2890(12) 0.6286(15) 0.061(5) Uani 1 1 d . . . . .
H8A H 0.1470 0.2934 0.7145 0.074 Uiso 1 1 calc R U . . .
C9 C 0.1032(7) 0.2956(13) 0.4132(18) 0.071(5) Uani 1 1 d . . . . .
H9A H 0.1050 0.3063 0.3222 0.085 Uiso 1 1 calc R U . . .
O5 O 0.2033(10) 0.2327(13) 0.0202(12) 0.115(6) Uani 1 1 d D . . . .
H5A H 0.237(7) 0.23(2) 0.08(2) 0.20(17) Uiso 1 1 d D . . . .
H5B H 0.177(10) 0.192(16) 0.04(3) 0.25(17) Uiso 1 1 d D . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Er O3 2.203(10) . ?
Er O3 2.203(10) 2_655 ?
Er O1 2.304(7) 2_655 ?
Er O1 2.304(7) . ?
Er O4 2.327(14) . ?
Er O2 2.371(9) . ?
Er O2 2.371(9) 2_655 ?
O1 C1 1.246(13) . ?
C1 O3 1.241(15) 5_666 ?
C1 C2 1.498(15) . ?
N1 C9 1.359(19) . ?
N1 C8 1.397(17) . ?
N1 C5 1.459(15) . ?
O2 H2A 0.8500 . ?
O2 H2B 0.8500 . ?
C2 C7 1.366(17) . ?
C2 C3 1.436(14) . ?
N2 C8 1.304(17) . ?
N2 N3 1.360(16) . ?
O3 C1 1.241(15) 5_666 ?
N3 C9 1.311(17) . ?
C3 C4 1.345(18) . ?
C3 H3C 0.9300 . ?
O4 H4A 0.8200 . ?
C4 C5 1.321(19) . ?
C4 H4B 0.9300 . ?
C5 C6 1.396(17) . ?
C6 C7 1.393(18) . ?
C6 H6A 0.9300 . ?
C7 H7A 0.9300 . ?
C8 H8A 0.9300 . ?
C9 H9A 0.9300 . ?
O5 H5A 0.86(2) . ?
O5 H5B 0.86(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 Er O3 174.5(6) . 2_655 ?
O3 Er O1 82.0(3) . 2_655 ?
O3 Er O1 99.5(3) 2_655 2_655 ?
O3 Er O1 99.5(3) . . ?
O3 Er O1 82.0(3) 2_655 . ?
O1 Er O1 148.1(5) 2_655 . ?
O3 Er O4 92.7(3) . . ?
O3 Er O4 92.7(3) 2_655 . ?
O1 Er O4 74.1(2) 2_655 . ?
O1 Er O4 74.1(2) . . ?
O3 Er O2 82.6(4) . . ?
O3 Er O2 92.8(4) 2_655 . ?
O1 Er O2 138.1(3) 2_655 . ?
O1 Er O2 73.0(3) . . ?
O4 Er O2 145.5(2) . . ?
O3 Er O2 92.8(4) . 2_655 ?
O3 Er O2 82.6(4) 2_655 2_655 ?
O1 Er O2 73.0(3) 2_655 2_655 ?
O1 Er O2 138.1(3) . 2_655 ?
O4 Er O2 145.5(2) . 2_655 ?
O2 Er O2 69.0(4) . 2_655 ?
C1 O1 Er 136.2(8) . . ?
O3 C1 O1 126.8(10) 5_666 . ?
O3 C1 C2 118.0(9) 5_666 . ?
O1 C1 C2 115.2(10) . . ?
C9 N1 C8 103.5(12) . . ?
C9 N1 C5 131.0(12) . . ?
C8 N1 C5 125.3(12) . . ?
Er O2 H2A 120.0 . . ?
Er O2 H2B 120.0 . . ?
H2A O2 H2B 120.0 . . ?
C7 C2 C3 116.2(11) . . ?
C7 C2 C1 123.0(10) . . ?
C3 C2 C1 120.8(11) . . ?
C8 N2 N3 108.2(11) . . ?
C1 O3 Er 172.6(9) 5_666 . ?
C9 N3 N2 107.5(13) . . ?
C4 C3 C2 122.0(12) . . ?
C4 C3 H3C 119.0 . . ?
C2 C3 H3C 119.0 . . ?
Er O4 H4A 109.5 . . ?
C5 C4 C3 119.3(12) . . ?
C5 C4 H4B 120.4 . . ?
C3 C4 H4B 120.4 . . ?
C4 C5 C6 123.5(13) . . ?
C4 C5 N1 121.3(11) . . ?
C6 C5 N1 115.2(12) . . ?
C7 C6 C5 116.6(13) . . ?
C7 C6 H6A 121.7 . . ?
C5 C6 H6A 121.7 . . ?
C2 C7 C6 122.4(11) . . ?
C2 C7 H7A 118.8 . . ?
C6 C7 H7A 118.8 . . ?
N2 C8 N1 109.7(13) . . ?
N2 C8 H8A 125.2 . . ?
N1 C8 H8A 125.2 . . ?
N3 C9 N1 111.0(15) . . ?
N3 C9 H9A 124.5 . . ?
N1 C9 H9A 124.5 . . ?
H5A O5 H5B 109(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Er O1 C1 O3 3(2) . . . 5_666 ?
Er O1 C1 C2 -175.8(8) . . . . ?
O3 C1 C2 C7 -176.2(14) 5_666 . . . ?
O1 C1 C2 C7 2.4(19) . . . . ?
O3 C1 C2 C3 4.8(19) 5_666 . . . ?
O1 C1 C2 C3 -176.5(13) . . . . ?
C8 N2 N3 C9 -2(2) . . . . ?
C7 C2 C3 C4 3(2) . . . . ?
C1 C2 C3 C4 -178.5(14) . . . . ?
C2 C3 C4 C5 1(2) . . . . ?
C3 C4 C5 C6 -4(3) . . . . ?
C3 C4 C5 N1 179.2(14) . . . . ?
C9 N1 C5 C4 175.0(17) . . . . ?
C8 N1 C5 C4 -12(2) . . . . ?
C9 N1 C5 C6 -2(2) . . . . ?
C8 N1 C5 C6 170.5(15) . . . . ?
C4 C5 C6 C7 3(2) . . . . ?
N1 C5 C6 C7 -179.9(13) . . . . ?
C3 C2 C7 C6 -3(2) . . . . ?
C1 C2 C7 C6 177.7(14) . . . . ?
C5 C6 C7 C2 1(2) . . . . ?
N3 N2 C8 N1 2.7(19) . . . . ?
C9 N1 C8 N2 -1.9(18) . . . . ?
C5 N1 C8 N2 -176.2(13) . . . . ?
N2 N3 C9 N1 1(2) . . . . ?
C8 N1 C9 N3 0.3(19) . . . . ?
C5 N1 C9 N3 174.2(14) . . . . ?

_refine_diff_density_max         3.690
_refine_diff_density_min         -1.372
_refine_diff_density_rms         0.250

# SQUEEZE RESULTS (Version = 201115)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.500 0.000 0.004 449 53 ' '
2 0.000 0.500 -0.052 449 53 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          ?

# start Validation Reply Form
_vrf_PLAT417_X                   
;
PROBLEM: Short Inter D-H..H-D       H5A    ..  H5A     ..       1.90 Ang.  
RESPONSE: This problem are caused by the disorder water molecules.
;
_vrf_PLAT420_X                   
;
PROBLEM: D-H Without Acceptor       O2     --  H2A    ...     Please Check 
RESPONSE: There are large amount of disorder water molecules in this crystal structure, some of these molecules are taken out with the squeeze restraint and give rise to the hydrogen riding on O2 or O5 have no acceptor.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_X
_database_code_depnum_ccdc_archive 'CCDC 1414833'
_audit_update_record             
;
2016-02-25 deposited with the CCDC.
2016-03-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H23 N6 O8 Sm, Cl O4'
_chemical_formula_sum            'C20 H23 Cl N6 O12 Sm'
_chemical_formula_weight         725.25

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sm Sm -0.1638 3.4418 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   12.668(3)
_cell_length_b                   15.483(3)
_cell_length_c                   14.625(3)
_cell_angle_alpha                90
_cell_angle_beta                 113.28(3)
_cell_angle_gamma                90
_cell_volume                     2635.0(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4857
_cell_measurement_theta_min      1.807
_cell_measurement_theta_max      25.242

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.828
_exptl_crystal_F_000             1440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    2.403
_shelx_estimated_absorpt_T_min   0.645
_shelx_estimated_absorpt_T_max   0.795
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4857
_diffrn_reflns_av_unetI/netI     0.1992
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_theta_min         1.807
_diffrn_reflns_theta_max         25.402
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4848
_reflns_number_gt                2447
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0170P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4848
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1681
_refine_ls_R_factor_gt           0.0771
_refine_ls_wR_factor_ref         0.1281
_refine_ls_wR_factor_gt          0.1076
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
Sm Sm 0.97276(6) 0.13263(4) 0.39972(5) 0.02445(17) Uani 1 1 d . . . . .
O1 O 0.8341(7) 0.1047(5) 0.4669(6) 0.030(2) Uani 1 1 d . . . . .
N1 N 0.4823(8) 0.0580(7) 0.6798(8) 0.032(3) Uani 1 1 d . . . . .
C1 C 0.8229(11) 0.0409(9) 0.5155(10) 0.031 Uani 1 1 d . . . . .
N2 N 0.3623(9) 0.0277(7) 0.7471(9) 0.041(3) Uani 1 1 d . . . . .
O2 O 0.8043(7) 0.1739(5) 0.2612(6) 0.044(3) Uani 1 1 d . . . . .
H2A H 0.7734 0.2228 0.2601 0.052 Uiso 1 1 d R U . . .
H2B H 0.7754 0.1395 0.2123 0.052 Uiso 1 1 d R U . . .
C2 C 0.7280(11) 0.0395(8) 0.5539(10) 0.032 Uani 1 1 d . . . . .
N3 N 0.3922(9) 0.1133(7) 0.7677(8) 0.044(3) Uani 1 1 d . . . . .
O3 O 1.0719(7) 0.1565(5) 0.5798(6) 0.039(2) Uani 1 1 d . . . . .
H3B H 1.1153 0.2005 0.5901 0.046 Uiso 1 1 d R U . . .
H3D H 1.0222 0.1652 0.6044 0.046 Uiso 1 1 d R U . . .
C3 C 0.7014(11) -0.0303(8) 0.5961(9) 0.032(3) Uani 1 1 d . . . . .
H3C H 0.7397 -0.0822 0.5996 0.038 Uiso 1 1 calc R U . . .
N4 N 1.3940(9) 0.5462(6) 0.3435(7) 0.027(3) Uani 1 1 d . . . . .
C4 C 0.6171(10) -0.0249(8) 0.6341(9) 0.028(3) Uani 1 1 d . . . . .
H4A H 0.6000 -0.0732 0.6635 0.034 Uiso 1 1 calc R U . . .
O4 O 1.1070(7) 0.0215(6) 0.4603(6) 0.037(2) Uani 1 1 d . . . . .
N5 N 1.4390(11) 0.6751(7) 0.3078(9) 0.051(4) Uani 1 1 d . . . . .
C5 C 0.5588(9) 0.0507(8) 0.6289(8) 0.023(3) Uani 1 1 d . . . . .
O5 O 0.8783(6) 0.0015(5) 0.3132(5) 0.026(2) Uani 1 1 d . . . . .
H5A H 0.9177 -0.0508 0.3270 0.031 Uiso 1 1 d R U . . .
H5B H 0.8029 0.0038 0.2665 0.031 Uiso 1 1 d R U . . .
N6 N 1.4752(8) 0.6124(6) 0.2562(7) 0.024(2) Uani 1 1 d . . . . .
C6 C 0.5812(9) 0.1210(8) 0.5843(8) 0.027(3) Uani 1 1 d . . . . .
H6B H 0.5393 0.1715 0.5792 0.033 Uiso 1 1 calc R U . . .
O7 O 1.1332(7) 0.2215(6) 0.4222(6) 0.037 Uani 1 1 d . . . . .
C7 C 0.6651(10) 0.1188(8) 0.5465(8) 0.036(3) Uani 1 1 d . . . . .
H7A H 0.6809 0.1675 0.5169 0.043 Uiso 1 1 calc R U . . .
O6 O 1.2183(9) 0.2676(6) 0.5766(7) 0.060(3) Uani 1 1 d . . . . .
C8 C 0.4161(11) -0.0027(9) 0.7011(11) 0.040(4) Uani 1 1 d . . . . .
H8A H 0.4126 -0.0604 0.6827 0.048 Uiso 1 1 calc R U . . .
C9 C 0.4623(10) 0.1273(10) 0.7260(10) 0.039(4) Uani 1 1 d . . . . .
H9A H 0.4965 0.1808 0.7275 0.047 Uiso 1 1 calc R U . . .
C10 C 1.1934(11) 0.2754(8) 0.4854(8) 0.029(3) Uani 1 1 d . . . . .
C11 C 1.2503(10) 0.3467(7) 0.4534(9) 0.026(3) Uani 1 1 d . . . . .
C12 C 1.2914(11) 0.4220(8) 0.5087(9) 0.037(4) Uani 1 1 d . . . . .
H12A H 1.2849 0.4289 0.5695 0.044 Uiso 1 1 calc R U . . .
C13 C 1.3411(11) 0.4859(8) 0.4741(10) 0.037(4) Uani 1 1 d . . . . .
H13A H 1.3707 0.5347 0.5128 0.044 Uiso 1 1 calc R U . . .
C14 C 1.3476(10) 0.4787(8) 0.3845(9) 0.026(3) Uani 1 1 d . . . . .
C15 C 1.3031(10) 0.4079(8) 0.3261(9) 0.033(3) Uani 1 1 d . . . . .
H15A H 1.3039 0.4049 0.2628 0.040 Uiso 1 1 calc R U . . .
C16 C 1.2566(10) 0.3399(8) 0.3611(9) 0.034(4) Uani 1 1 d . . . . .
H16A H 1.2300 0.2905 0.3228 0.041 Uiso 1 1 calc R U . . .
C17 C 1.3904(11) 0.6322(10) 0.3587(10) 0.046(4) Uani 1 1 d . . . . .
H17A H 1.3581 0.6574 0.3994 0.055 Uiso 1 1 calc R U . . .
C18 C 1.4495(11) 0.5400(8) 0.2834(10) 0.033(3) Uani 1 1 d . . . . .
H18A H 1.4679 0.4873 0.2629 0.040 Uiso 1 1 calc R U . . .
O8 O 0.9102(8) 0.2812(5) 0.4272(7) 0.041(3) Uani 1 1 d . . . . .
C19 C 0.8740(17) 0.3219(12) 0.4925(12) 0.084(7) Uani 1 1 d . . . . .
H19A H 0.8730 0.2796 0.5411 0.101 Uiso 1 1 calc R U . . .
H19B H 0.7952 0.3402 0.4559 0.101 Uiso 1 1 calc R U . . .
C20 C 0.9356(17) 0.3926(14) 0.5438(14) 0.130(10) Uani 1 1 d . . . . .
H20A H 0.9011 0.4148 0.5868 0.194 Uiso 1 1 calc R U . . .
H20B H 1.0134 0.3756 0.5830 0.194 Uiso 1 1 calc R U . . .
H20C H 0.9352 0.4365 0.4974 0.194 Uiso 1 1 calc R U . . .
Cl Cl 1.5184(4) 0.2720(3) 0.3017(3) 0.0524(11) Uani 1 1 d . . . . .
O9 O 1.5549(11) 0.3197(9) 0.3875(10) 0.129(6) Uani 1 1 d . . . . .
O10 O 1.4658(9) 0.3291(7) 0.2181(7) 0.070(4) Uani 1 1 d . . . . .
O11 O 1.4344(14) 0.2167(8) 0.3009(15) 0.154(8) Uani 1 1 d . . . . .
O12 O 1.6067(11) 0.2232(8) 0.2898(11) 0.113(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
Sm O4 2.334(8) . ?
Sm O1 2.367(7) . ?
Sm O7 2.367(9) . ?
Sm O2 2.376(8) . ?
Sm O5 2.441(7) . ?
Sm O3 2.457(8) . ?
Sm O8 2.516(8) . ?
Sm N6 2.630(10) 2_745 ?
O1 C1 1.257(13) . ?
N1 C9 1.344(15) . ?
N1 C8 1.375(15) . ?
N1 C5 1.442(13) . ?
C1 O4 1.265(14) 3_756 ?
C1 C2 1.515(16) . ?
N2 C8 1.225(15) . ?
N2 N3 1.379(14) . ?
O2 H2A 0.8499 . ?
O2 H2B 0.8500 . ?
C2 C3 1.352(16) . ?
C2 C7 1.445(16) . ?
N3 C9 1.279(14) . ?
O3 H3B 0.8499 . ?
O3 H3D 0.8501 . ?
C3 C4 1.387(15) . ?
C3 H3C 0.9300 . ?
N4 C18 1.329(14) . ?
N4 C17 1.353(16) . ?
N4 C14 1.442(14) . ?
C4 C5 1.370(15) . ?
C4 H4A 0.9300 . ?
O4 C1 1.265(14) 3_756 ?
N5 C17 1.319(15) . ?
N5 N6 1.414(13) . ?
C5 C6 1.355(15) . ?
O5 H5A 0.9299 . ?
O5 H5B 0.9300 . ?
N6 C18 1.274(14) . ?
N6 Sm 2.630(10) 2_755 ?
C6 C7 1.379(14) . ?
C6 H6B 0.9300 . ?
O7 C10 1.255(14) . ?
C7 H7A 0.9300 . ?
O6 C10 1.249(13) . ?
C8 H8A 0.9300 . ?
C9 H9A 0.9300 . ?
C10 C11 1.492(16) . ?
C11 C16 1.386(16) . ?
C11 C12 1.397(15) . ?
C12 C13 1.373(15) . ?
C12 H12A 0.9300 . ?
C13 C14 1.349(15) . ?
C13 H13A 0.9300 . ?
C14 C15 1.366(16) . ?
C15 C16 1.399(15) . ?
C15 H15A 0.9300 . ?
C16 H16A 0.9300 . ?
C17 H17A 0.9300 . ?
C18 H18A 0.9300 . ?
O8 C19 1.367(17) . ?
C19 C20 1.38(2) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
Cl O11 1.363(13) . ?
Cl O9 1.369(12) . ?
Cl O12 1.417(11) . ?
Cl O10 1.441(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 Sm O1 104.9(3) . . ?
O4 Sm O7 85.4(3) . . ?
O1 Sm O7 141.8(3) . . ?
O4 Sm O2 142.7(3) . . ?
O1 Sm O2 80.7(3) . . ?
O7 Sm O2 113.3(3) . . ?
O4 Sm O5 73.6(3) . . ?
O1 Sm O5 76.7(3) . . ?
O7 Sm O5 140.7(3) . . ?
O2 Sm O5 72.0(3) . . ?
O4 Sm O3 73.6(3) . . ?
O1 Sm O3 74.4(3) . . ?
O7 Sm O3 73.5(3) . . ?
O2 Sm O3 141.2(3) . . ?
O5 Sm O3 128.2(2) . . ?
O4 Sm O8 147.3(3) . . ?
O1 Sm O8 76.6(3) . . ?
O7 Sm O8 75.7(3) . . ?
O2 Sm O8 70.0(3) . . ?
O5 Sm O8 136.2(3) . . ?
O3 Sm O8 75.6(3) . . ?
O4 Sm N6 81.2(3) . 2_745 ?
O1 Sm N6 145.0(3) . 2_745 ?
O7 Sm N6 72.2(3) . 2_745 ?
O2 Sm N6 75.0(3) . 2_745 ?
O5 Sm N6 72.0(3) . 2_745 ?
O3 Sm N6 138.6(3) . 2_745 ?
O8 Sm N6 116.7(3) . 2_745 ?
C1 O1 Sm 130.2(8) . . ?
C9 N1 C8 100.3(10) . . ?
C9 N1 C5 128.4(11) . . ?
C8 N1 C5 131.2(11) . . ?
O1 C1 O4 122.3(12) . 3_756 ?
O1 C1 C2 120.3(12) . . ?
O4 C1 C2 117.3(12) 3_756 . ?
C8 N2 N3 108.8(11) . . ?
Sm O2 H2A 120.5 . . ?
Sm O2 H2B 119.5 . . ?
H2A O2 H2B 120.0 . . ?
C3 C2 C7 118.9(11) . . ?
C3 C2 C1 123.9(12) . . ?
C7 C2 C1 117.1(12) . . ?
C9 N3 N2 104.1(11) . . ?
Sm O3 H3B 109.4 . . ?
Sm O3 H3D 109.1 . . ?
H3B O3 H3D 109.5 . . ?
C2 C3 C4 120.4(12) . . ?
C2 C3 H3C 119.8 . . ?
C4 C3 H3C 119.8 . . ?
C18 N4 C17 104.0(10) . . ?
C18 N4 C14 129.2(11) . . ?
C17 N4 C14 126.8(11) . . ?
C5 C4 C3 120.8(12) . . ?
C5 C4 H4A 119.6 . . ?
C3 C4 H4A 119.6 . . ?
C1 O4 Sm 174.5(9) 3_756 . ?
C17 N5 N6 106.1(10) . . ?
C6 C5 C4 120.2(11) . . ?
C6 C5 N1 119.7(11) . . ?
C4 C5 N1 119.7(11) . . ?
Sm O5 H5A 120.0 . . ?
Sm O5 H5B 120.0 . . ?
H5A O5 H5B 120.0 . . ?
C18 N6 N5 105.1(10) . . ?
C18 N6 Sm 123.9(8) . 2_755 ?
N5 N6 Sm 128.8(7) . 2_755 ?
C5 C6 C7 120.9(12) . . ?
C5 C6 H6B 119.5 . . ?
C7 C6 H6B 119.5 . . ?
C10 O7 Sm 136.7(8) . . ?
C6 C7 C2 118.8(12) . . ?
C6 C7 H7A 120.6 . . ?
C2 C7 H7A 120.6 . . ?
N2 C8 N1 112.6(12) . . ?
N2 C8 H8A 123.7 . . ?
N1 C8 H8A 123.7 . . ?
N3 C9 N1 114.1(13) . . ?
N3 C9 H9A 123.0 . . ?
N1 C9 H9A 123.0 . . ?
O6 C10 O7 123.0(12) . . ?
O6 C10 C11 117.2(12) . . ?
O7 C10 C11 119.3(11) . . ?
C16 C11 C12 118.4(11) . . ?
C16 C11 C10 118.0(11) . . ?
C12 C11 C10 123.5(11) . . ?
C13 C12 C11 120.5(11) . . ?
C13 C12 H12A 119.7 . . ?
C11 C12 H12A 119.7 . . ?
C14 C13 C12 120.7(12) . . ?
C14 C13 H13A 119.6 . . ?
C12 C13 H13A 119.6 . . ?
C13 C14 C15 120.4(12) . . ?
C13 C14 N4 122.3(11) . . ?
C15 C14 N4 117.2(11) . . ?
C14 C15 C16 120.2(12) . . ?
C14 C15 H15A 119.9 . . ?
C16 C15 H15A 119.9 . . ?
C11 C16 C15 119.6(11) . . ?
C11 C16 H16A 120.2 . . ?
C15 C16 H16A 120.2 . . ?
N5 C17 N4 110.4(12) . . ?
N5 C17 H17A 124.8 . . ?
N4 C17 H17A 124.8 . . ?
N6 C18 N4 114.2(12) . . ?
N6 C18 H18A 122.9 . . ?
N4 C18 H18A 122.9 . . ?
C19 O8 Sm 138.4(9) . . ?
O8 C19 C20 118.1(19) . . ?
O8 C19 H19A 107.8 . . ?
C20 C19 H19A 107.8 . . ?
O8 C19 H19B 107.8 . . ?
C20 C19 H19B 107.8 . . ?
H19A C19 H19B 107.1 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O11 Cl O9 109.1(11) . . ?
O11 Cl O12 108.3(9) . . ?
O9 Cl O12 113.8(9) . . ?
O11 Cl O10 106.3(9) . . ?
O9 Cl O10 108.8(8) . . ?
O12 Cl O10 110.3(8) . . ?

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
Sm O1 C1 O4 2.3(19) . . . 3_756 ?
Sm O1 C1 C2 177.9(8) . . . . ?
O1 C1 C2 C3 171.7(12) . . . . ?
O4 C1 C2 C3 -13(2) 3_756 . . . ?
O1 C1 C2 C7 -9.9(19) . . . . ?
O4 C1 C2 C7 165.9(11) 3_756 . . . ?
C8 N2 N3 C9 2.5(17) . . . . ?
C7 C2 C3 C4 -2(2) . . . . ?
C1 C2 C3 C4 176.6(12) . . . . ?
C2 C3 C4 C5 1(2) . . . . ?
C3 C4 C5 C6 1.4(19) . . . . ?
C3 C4 C5 N1 -172.2(11) . . . . ?
C9 N1 C5 C6 -29.6(19) . . . . ?
C8 N1 C5 C6 155.3(14) . . . . ?
C9 N1 C5 C4 144.0(14) . . . . ?
C8 N1 C5 C4 -31(2) . . . . ?
C17 N5 N6 C18 -2.3(14) . . . . ?
C17 N5 N6 Sm 161.1(9) . . . 2_755 ?
C4 C5 C6 C7 -2.1(18) . . . . ?
N1 C5 C6 C7 171.4(10) . . . . ?
C5 C6 C7 C2 0.9(18) . . . . ?
C3 C2 C7 C6 1.1(19) . . . . ?
C1 C2 C7 C6 -177.4(11) . . . . ?
N3 N2 C8 N1 -3.7(18) . . . . ?
C9 N1 C8 N2 3.2(16) . . . . ?
C5 N1 C8 N2 179.2(12) . . . . ?
N2 N3 C9 N1 -0.4(17) . . . . ?
C8 N1 C9 N3 -1.5(16) . . . . ?
C5 N1 C9 N3 -177.7(12) . . . . ?
Sm O7 C10 O6 36(2) . . . . ?
Sm O7 C10 C11 -151.4(9) . . . . ?
O6 C10 C11 C16 158.3(12) . . . . ?
O7 C10 C11 C16 -14.5(19) . . . . ?
O6 C10 C11 C12 -26(2) . . . . ?
O7 C10 C11 C12 161.6(12) . . . . ?
C16 C11 C12 C13 -3(2) . . . . ?
C10 C11 C12 C13 -178.9(12) . . . . ?
C11 C12 C13 C14 2(2) . . . . ?
C12 C13 C14 C15 1(2) . . . . ?
C12 C13 C14 N4 176.9(12) . . . . ?
C18 N4 C14 C13 149.1(14) . . . . ?
C17 N4 C14 C13 -31(2) . . . . ?
C18 N4 C14 C15 -34.8(19) . . . . ?
C17 N4 C14 C15 145.3(13) . . . . ?
C13 C14 C15 C16 -4(2) . . . . ?
N4 C14 C15 C16 -180.0(10) . . . . ?
C12 C11 C16 C15 -0.1(19) . . . . ?
C10 C11 C16 C15 176.2(11) . . . . ?
C14 C15 C16 C11 3.3(19) . . . . ?
N6 N5 C17 N4 0.4(16) . . . . ?
C18 N4 C17 N5 1.5(16) . . . . ?
C14 N4 C17 N5 -178.5(12) . . . . ?
N5 N6 C18 N4 3.5(15) . . . . ?
Sm N6 C18 N4 -161.0(8) 2_755 . . . ?
C17 N4 C18 N6 -3.2(16) . . . . ?
C14 N4 C18 N6 176.8(11) . . . . ?
Sm O8 C19 C20 122.3(16) . . . . ?

_refine_diff_density_max         1.108
_refine_diff_density_min         -1.470
_refine_diff_density_rms         0.210

####################################################################### 
# 
# 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_X
_database_code_depnum_ccdc_archive 'CCDC 1430646'
_audit_update_record             
;
2016-02-25 deposited with the CCDC.
2016-03-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H18 Lu N6 O7, 2(H2 O)'
_chemical_formula_sum            'C18 H22 Lu N6 O9'
_chemical_formula_weight         641.39

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'
Lu Lu -0.4720 5.8584 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -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                   21.218(4)
_cell_length_b                   14.370(3)
_cell_length_c                   9.954(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.35(3)
_cell_angle_gamma                90
_cell_volume                     3016.4(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2781
_cell_measurement_theta_min      1.715
_cell_measurement_theta_max      25.416

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_F_000             1260
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    3.319
_shelx_estimated_absorpt_T_min   0.354
_shelx_estimated_absorpt_T_max   0.560
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2781
_diffrn_reflns_av_unetI/netI     0.0812
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_theta_min         1.715
_diffrn_reflns_theta_max         25.416
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2764
_reflns_number_gt                2186
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+8.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2764
_refine_ls_number_parameters     155
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0920
_refine_ls_R_factor_gt           0.0696
_refine_ls_wR_factor_ref         0.1773
_refine_ls_wR_factor_gt          0.1649
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.089
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
Lu Lu 0.5000 -0.01763(5) 0.2500 0.0307(3) Uani 1 2 d S T P . .
O1 O 0.5859(3) 0.0279(6) 0.1511(7) 0.0377(18) Uani 1 1 d . . . . .
N1 N 0.9469(5) 0.2354(10) 0.0406(13) 0.065(3) Uani 1 1 d . . . . .
C1 C 0.8959(6) 0.2019(11) 0.0870(15) 0.061(4) Uani 1 1 d . . . . .
H1B H 0.8914 0.1954 0.1784 0.073 Uiso 1 1 calc R U . . .
N2 N 0.9317(5) 0.2402(8) -0.1005(15) 0.063(3) Uani 1 1 d . . . . .
C2 C 0.8739(6) 0.2082(11) -0.1307(17) 0.068(4) Uani 1 1 d . . . . .
H2B H 0.8519 0.2061 -0.2168 0.082 Uiso 1 1 calc R U . . .
O2 O 0.5000 0.1414(8) 0.2500 0.054(3) Uani 1 2 d S T P . .
H2A H 0.5220 0.1710 0.1978 0.064 Uiso 1 1 d R U . . .
O3 O 0.4325(3) -0.0230(6) 0.0708(9) 0.046(2) Uani 1 1 d . . . . .
N3 N 0.8511(5) 0.1782(8) -0.0131(11) 0.054(3) Uani 1 1 d . . . . .
C3 C 0.7893(5) 0.1385(8) 0.0030(11) 0.037 Uani 1 1 d . . . . .
O4 O 0.5415(4) -0.1508(6) 0.1580(8) 0.048(2) Uani 1 1 d . . . . .
H4C H 0.5840 -0.1618 0.1984 0.072 Uiso 1 1 d R U . . .
H4D H 0.5415 -0.1421 0.0624 0.072 Uiso 1 1 d R U . . .
C4 C 0.7503(6) 0.1150(11) -0.1170(15) 0.061(4) Uani 1 1 d . . . . .
H4B H 0.7641 0.1207 -0.2021 0.073 Uiso 1 1 calc R U . . .
C5 C 0.6887(5) 0.0822(10) -0.0989(12) 0.050(3) Uani 1 1 d . . . . .
H5A H 0.6612 0.0662 -0.1745 0.060 Uiso 1 1 calc R U . . .
C6 C 0.6694(5) 0.0737(8) 0.0227(11) 0.035(2) Uani 1 1 d . . . . .
C7 C 0.7084(6) 0.0933(10) 0.1372(12) 0.050(3) Uani 1 1 d . . . . .
H7A H 0.6947 0.0839 0.2217 0.060 Uiso 1 1 calc R U . . .
C8 C 0.7690(5) 0.1273(11) 0.1267(14) 0.062(4) Uani 1 1 d . . . . .
H8A H 0.7956 0.1423 0.2043 0.074 Uiso 1 1 calc R U . . .
C9 C 0.6022(4) 0.0386(7) 0.0364(11) 0.028(2) Uani 1 1 d . . . . .
O5 O 0.8004(9) 0.2595(14) 0.4781(11) 0.153(8) Uani 1 1 d D . . . .
H5B H 0.828(8) 0.290(15) 0.437(19) 0.183 Uiso 1 1 d D U . . .
H5C H 0.774(8) 0.233(16) 0.417(16) 0.183 Uiso 1 1 d D U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Lu O3 2.162(8) 2_655 ?
Lu O3 2.162(8) . ?
Lu O1 2.262(7) . ?
Lu O1 2.262(7) 2_655 ?
Lu O2 2.286(12) . ?
Lu O4 2.336(8) . ?
Lu O4 2.336(8) 2_655 ?
O1 C9 1.238(13) . ?
N1 C1 1.315(15) . ?
N1 N2 1.407(17) . ?
C1 N3 1.343(16) . ?
C1 H1B 0.9300 . ?
N2 C2 1.313(16) . ?
C2 N3 1.384(18) . ?
C2 H2B 0.9300 . ?
O2 H2A 0.8500 . ?
O3 C9 1.248(13) 5_655 ?
N3 C3 1.456(14) . ?
C3 C8 1.359(17) . ?
C3 C4 1.416(18) . ?
O4 H4C 0.9600 . ?
O4 H4D 0.9601 . ?
C4 C5 1.418(15) . ?
C4 H4B 0.9300 . ?
C5 C6 1.327(16) . ?
C5 H5A 0.9300 . ?
C6 C7 1.362(15) . ?
C6 C9 1.532(13) . ?
C7 C8 1.389(16) . ?
C7 H7A 0.9300 . ?
C8 H8A 0.9300 . ?
C9 O3 1.248(13) 5_655 ?
O5 H5C 0.87(2) . ?
O5 H5B 0.87(2) . ?
O5 H5C 0.87(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 Lu O3 175.9(5) 2_655 . ?
O3 Lu O1 83.0(3) 2_655 . ?
O3 Lu O1 98.2(3) . . ?
O3 Lu O1 98.2(3) 2_655 2_655 ?
O3 Lu O1 83.0(3) . 2_655 ?
O1 Lu O1 146.4(4) . 2_655 ?
O3 Lu O2 92.1(2) 2_655 . ?
O3 Lu O2 92.1(2) . . ?
O1 Lu O2 73.2(2) . . ?
O1 Lu O2 73.2(2) 2_655 . ?
O3 Lu O4 92.9(3) 2_655 . ?
O3 Lu O4 83.7(3) . . ?
O1 Lu O4 73.1(3) . . ?
O1 Lu O4 139.8(3) 2_655 . ?
O2 Lu O4 145.0(2) . . ?
O3 Lu O4 83.7(3) 2_655 2_655 ?
O3 Lu O4 92.9(3) . 2_655 ?
O1 Lu O4 139.8(3) . 2_655 ?
O1 Lu O4 73.1(3) 2_655 2_655 ?
O2 Lu O4 145.0(2) . 2_655 ?
O4 Lu O4 69.9(4) . 2_655 ?
C9 O1 Lu 139.3(7) . . ?
C1 N1 N2 105.1(11) . . ?
N1 C1 N3 112.0(13) . . ?
N1 C1 H1B 124.0 . . ?
N3 C1 H1B 124.0 . . ?
C2 N2 N1 108.5(12) . . ?
N2 C2 N3 108.6(14) . . ?
N2 C2 H2B 125.7 . . ?
N3 C2 H2B 125.7 . . ?
Lu O2 H2A 120.0 . . ?
C9 O3 Lu 170.6(8) 5_655 . ?
C1 N3 C2 105.3(10) . . ?
C1 N3 C3 126.2(11) . . ?
C2 N3 C3 128.2(11) . . ?
C8 C3 C4 121.4(11) . . ?
C8 C3 N3 121.7(10) . . ?
C4 C3 N3 116.8(10) . . ?
Lu O4 H4C 110.3 . . ?
Lu O4 H4D 108.8 . . ?
H4C O4 H4D 109.5 . . ?
C3 C4 C5 115.6(12) . . ?
C3 C4 H4B 122.2 . . ?
C5 C4 H4B 122.2 . . ?
C6 C5 C4 121.9(12) . . ?
C6 C5 H5A 119.0 . . ?
C4 C5 H5A 119.0 . . ?
C5 C6 C7 121.6(10) . . ?
C5 C6 C9 119.8(10) . . ?
C7 C6 C9 118.6(10) . . ?
C6 C7 C8 119.4(12) . . ?
C6 C7 H7A 120.3 . . ?
C8 C7 H7A 120.3 . . ?
C3 C8 C7 119.9(12) . . ?
C3 C8 H8A 120.0 . . ?
C7 C8 H8A 120.0 . . ?
O1 C9 O3 124.5(9) . 5_655 ?
O1 C9 C6 118.8(9) . . ?
O3 C9 C6 116.8(9) 5_655 . ?
H5C O5 H5B 108(3) . . ?
H5C O5 H5C 0(10) . . ?
H5B O5 H5C 108(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
N2 N1 C1 N3 4.8(18) . . . . ?
C1 N1 N2 C2 -1.2(17) . . . . ?
N1 N2 C2 N3 -2.7(17) . . . . ?
N1 C1 N3 C2 -6.4(17) . . . . ?
N1 C1 N3 C3 179.6(13) . . . . ?
N2 C2 N3 C1 5.4(17) . . . . ?
N2 C2 N3 C3 179.3(12) . . . . ?
C1 N3 C3 C8 5(2) . . . . ?
C2 N3 C3 C8 -168.0(15) . . . . ?
C1 N3 C3 C4 -177.4(14) . . . . ?
C2 N3 C3 C4 10(2) . . . . ?
C8 C3 C4 C5 2(2) . . . . ?
N3 C3 C4 C5 -176.0(12) . . . . ?
C3 C4 C5 C6 0(2) . . . . ?
C4 C5 C6 C7 -2(2) . . . . ?
C4 C5 C6 C9 179.6(12) . . . . ?
C5 C6 C7 C8 3(2) . . . . ?
C9 C6 C7 C8 -178.5(12) . . . . ?
C4 C3 C8 C7 -1(2) . . . . ?
N3 C3 C8 C7 176.9(13) . . . . ?
C6 C7 C8 C3 -2(2) . . . . ?
Lu O1 C9 O3 -0.2(18) . . . 5_655 ?
Lu O1 C9 C6 179.5(7) . . . . ?
C5 C6 C9 O1 177.4(11) . . . . ?
C7 C6 C9 O1 -0.9(16) . . . . ?
C5 C6 C9 O3 -2.9(16) . . . 5_655 ?
C7 C6 C9 O3 178.8(11) . . . 5_655 ?

_refine_diff_density_max         3.512
_refine_diff_density_min         -2.402
_refine_diff_density_rms         0.267

# SQUEEZE RESULTS (Version = 201115)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 -0.025 405 34 ' '
2 0.500 0.500 0.004 405 34 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          ?
# start Validation Reply Form
_vrf_PLAT420_X                   
;
PROBLEM:D-H Without Acceptor       O4     --  H4D    ...     Please Check 
 D-H Without Acceptor       O5     --  H5B    ...     Please Check 
 D-H Without Acceptor       O5     --  H5C    ...     Please Check 

RESPONSE: There are large amount of disorder water molecules in this crystal structure, some of these molecules are taken out with the squeeze restraint and give rise to the hydrogen riding on O4 or O5 have no acceptor.
;
# end Validation Reply Form


