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

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

data_1-Eu
_database_code_depnum_ccdc_archive 'CCDC 1439792'
_audit_update_record             
;
2016-02-01 deposited with the CCDC.
2016-02-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H9 Eu N O9 P, 3(H2 O)'
_chemical_formula_sum            'C8 H15 Eu N O12 P'
_chemical_formula_weight         500.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Eu Eu -0.1578 3.6682 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   9.7558(2)
_cell_length_b                   10.5549(2)
_cell_length_c                   16.5111(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.447(2)
_cell_angle_gamma                90.00
_cell_volume                     1571.36(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3930
_cell_measurement_theta_min      2.8763
_cell_measurement_theta_max      28.9149

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.114
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             976
_exptl_absorpt_coefficient_mu    4.155
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4418
_exptl_absorpt_correction_T_max  0.4758
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1954
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6297
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_sigmaI/netI    0.0286
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.88
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2766
_reflns_number_gt                2548
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
omit -2 50
ISOR 0.01 O11 O12
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0254P)²+4.6978P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2766
_refine_ls_number_parameters     209
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0278
_refine_ls_R_factor_gt           0.0247
_refine_ls_wR_factor_ref         0.0612
_refine_ls_wR_factor_gt          0.0593
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.052
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.3214(6) 1.0510(6) -0.0291(4) 0.0442(14) Uani 1 1 d . . .
H1 H -0.3926 1.1064 -0.0654 0.053 Uiso 1 1 calc R . .
C2 C -0.3538(7) 0.9248(7) -0.0280(5) 0.0587(19) Uani 1 1 d . . .
H2 H -0.4466 0.8944 -0.0640 0.070 Uiso 1 1 calc R . .
C3 C -0.2505(9) 0.8441(7) 0.0258(4) 0.063(2) Uani 1 1 d . . .
H3 H -0.2725 0.7586 0.0271 0.076 Uiso 1 1 calc R . .
C4 C -0.1126(8) 0.8902(5) 0.0784(4) 0.0480(15) Uani 1 1 d . . .
H4 H -0.0418 0.8352 0.1153 0.058 Uiso 1 1 calc R . .
C5 C -0.0789(5) 1.0165(5) 0.0768(3) 0.0304(11) Uani 1 1 d . . .
C6 C 0.0670(5) 1.0724(5) 0.1292(3) 0.0308(11) Uani 1 1 d . . .
H6A H 0.0904 1.1364 0.0943 0.037 Uiso 1 1 calc R . .
H6B H 0.1421 1.0068 0.1426 0.037 Uiso 1 1 calc R . .
C7 C -0.0717(4) 0.9673(4) 0.4681(3) 0.0218(9) Uani 1 1 d . . .
C8 C 0.5177(4) 0.9401(4) 0.5284(3) 0.0197(9) Uani 1 1 d . . .
Eu1 Eu 0.17947(2) 0.88824(2) 0.393348(12) 0.01686(9) Uani 1 1 d . . .
N1 N -0.1856(4) 1.0947(4) 0.0227(3) 0.0288(9) Uani 1 1 d . . .
O1 O 0.0602(3) 1.0407(3) 0.28972(19) 0.0261(7) Uani 1 1 d . . .
O2 O 0.2346(3) 1.2043(4) 0.2702(2) 0.0372(9) Uani 1 1 d . . .
H2A H 0.2862 1.1643 0.3138 0.056 Uiso 1 1 calc R . .
O3 O -0.0391(3) 1.2457(3) 0.21039(18) 0.0259(7) Uani 1 1 d . . .
O4 O -0.1560(4) 1.2166(3) 0.0178(2) 0.0312(8) Uani 1 1 d . . .
O5 O -0.1858(3) 0.9804(3) 0.4847(2) 0.0280(7) Uani 1 1 d . . .
O6 O -0.0618(3) 0.9092(3) 0.4054(2) 0.0282(8) Uani 1 1 d . . .
O7 O 0.4265(3) 0.8518(3) 0.5068(2) 0.0311(8) Uani 1 1 d . . .
O8 O 0.6395(3) 0.9408(3) 0.59289(19) 0.0275(7) Uani 1 1 d . . .
O9 O 0.3205(4) 0.8226(5) 0.3091(3) 0.0668(15) Uani 1 1 d . . .
H91 H 0.2837 0.7680 0.2780 0.100 Uiso 1 1 d R . .
H92 H 0.3985 0.8635 0.3116 0.100 Uiso 1 1 d R . .
O10 O 0.6006(5) 0.8742(7) 0.3237(4) 0.120(3) Uani 1 1 d . . .
H101 H 0.6489 0.8710 0.2935 0.180 Uiso 1 1 d R . .
H102 H 0.6476 0.9176 0.3715 0.180 Uiso 1 1 d R . .
O11 O 0.2811(9) 0.5317(11) 0.2788(6) 0.187(4) Uani 1 1 d U . .
H111 H 0.2844 0.4565 0.3021 0.281 Uiso 1 1 d R . .
H112 H 0.2080 0.5704 0.2859 0.281 Uiso 1 1 d R . .
O12 O 0.2457(16) 0.6985(15) 0.1612(9) 0.297(7) Uani 1 1 d U . .
H121 H 0.2452 0.6231 0.1795 0.445 Uiso 1 1 d R . .
H122 H 0.1866 0.6766 0.1096 0.445 Uiso 1 1 d R . .
P1 P 0.07484(12) 1.14356(12) 0.23056(7) 0.0215(3) 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
C1 N1 1.355(6) . ?
C1 C2 1.370(9) . ?
C1 H1 0.9300 . ?
C2 C3 1.358(10) . ?
C2 H2 0.9300 . ?
C3 C4 1.381(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.376(7) . ?
C4 H4 0.9300 . ?
C5 N1 1.361(6) . ?
C5 C6 1.477(7) . ?
C6 P1 1.810(5) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 O6 1.238(5) . ?
C7 O5 1.252(5) . ?
C7 C7 1.556(8) 3_576 ?
C7 Eu1 3.241(4) 3_576 ?
C8 O7 1.244(5) . ?
C8 O8 1.256(5) . ?
C8 C8 1.533(9) 3_676 ?
Eu1 O3 2.298(3) 2_545 ?
Eu1 O1 2.313(3) . ?
Eu1 O4 2.397(3) 2_545 ?
Eu1 O9 2.402(4) . ?
Eu1 O5 2.425(3) 3_576 ?
Eu1 O6 2.447(3) . ?
Eu1 O7 2.453(3) . ?
Eu1 O8 2.474(3) 3_676 ?
Eu1 C7 3.241(4) 3_576 ?
Eu1 H91 2.7842 . ?
N1 O4 1.327(5) . ?
O1 P1 1.503(3) . ?
O2 P1 1.577(3) . ?
O2 H2A 0.8200 . ?
O3 P1 1.492(3) . ?
O3 Eu1 2.298(3) 2 ?
O4 Eu1 2.397(3) 2 ?
O5 Eu1 2.425(3) 3_576 ?
O8 Eu1 2.474(3) 3_676 ?
O9 H91 0.7643 . ?
O9 H92 0.8618 . ?
O10 H101 0.8058 . ?
O10 H102 0.8751 . ?
O11 H111 0.8773 . ?
O11 H112 0.8677 . ?
O12 H121 0.8521 . ?
O12 H122 0.8582 . ?

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
N1 C1 C2 119.8(6) . . ?
N1 C1 H1 120.1 . . ?
C2 C1 H1 120.1 . . ?
C3 C2 C1 120.1(6) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 119.4(6) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C5 C4 C3 120.8(6) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
N1 C5 C4 118.1(5) . . ?
N1 C5 C6 117.8(5) . . ?
C4 C5 C6 124.0(5) . . ?
C5 C6 P1 113.5(3) . . ?
C5 C6 H6A 108.9 . . ?
P1 C6 H6A 108.9 . . ?
C5 C6 H6B 108.9 . . ?
P1 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
O6 C7 O5 126.7(4) . . ?
O6 C7 C7 116.7(5) . 3_576 ?
O5 C7 C7 116.6(5) . 3_576 ?
O6 C7 Eu1 166.7(3) . 3_576 ?
O5 C7 Eu1 40.3(2) . 3_576 ?
C7 C7 Eu1 76.3(3) 3_576 3_576 ?
O7 C8 O8 126.1(4) . . ?
O7 C8 C8 118.2(4) . 3_676 ?
O8 C8 C8 115.7(5) . 3_676 ?
O3 Eu1 O1 85.17(11) 2_545 . ?
O3 Eu1 O4 78.01(11) 2_545 2_545 ?
O1 Eu1 O4 147.14(11) . 2_545 ?
O3 Eu1 O9 71.92(12) 2_545 . ?
O1 Eu1 O9 90.57(15) . . ?
O4 Eu1 O9 110.25(16) 2_545 . ?
O3 Eu1 O5 144.28(10) 2_545 3_576 ?
O1 Eu1 O5 93.59(11) . 3_576 ?
O4 Eu1 O5 84.38(11) 2_545 3_576 ?
O9 Eu1 O5 143.78(12) . 3_576 ?
O3 Eu1 O6 78.57(11) 2_545 . ?
O1 Eu1 O6 76.68(11) . . ?
O4 Eu1 O6 72.45(12) 2_545 . ?
O9 Eu1 O6 148.74(12) . . ?
O5 Eu1 O6 66.50(10) 3_576 . ?
O3 Eu1 O7 126.78(11) 2_545 . ?
O1 Eu1 O7 138.09(11) . . ?
O4 Eu1 O7 73.11(11) 2_545 . ?
O9 Eu1 O7 77.54(13) . . ?
O5 Eu1 O7 75.47(11) 3_576 . ?
O6 Eu1 O7 130.29(11) . . ?
O3 Eu1 O8 138.36(10) 2_545 3_676 ?
O1 Eu1 O8 72.56(10) . 3_676 ?
O4 Eu1 O8 136.63(10) 2_545 3_676 ?
O9 Eu1 O8 73.56(13) . 3_676 ?
O5 Eu1 O8 73.49(11) 3_576 3_676 ?
O6 Eu1 O8 127.00(11) . 3_676 ?
O7 Eu1 O8 65.53(10) . 3_676 ?
O3 Eu1 C7 124.93(10) 2_545 3_576 ?
O1 Eu1 C7 89.31(11) . 3_576 ?
O4 Eu1 C7 77.92(12) 2_545 3_576 ?
O9 Eu1 C7 163.05(12) . 3_576 ?
O5 Eu1 C7 19.52(10) 3_576 3_576 ?
O6 Eu1 C7 47.04(10) . 3_576 ?
O7 Eu1 C7 91.33(11) . 3_576 ?
O8 Eu1 C7 90.27(11) 3_676 3_576 ?
O3 Eu1 H91 57.4 2_545 . ?
O1 Eu1 H91 91.3 . . ?
O4 Eu1 H91 102.7 2_545 . ?
O9 Eu1 H91 14.7 . . ?
O5 Eu1 H91 158.1 3_576 . ?
O6 Eu1 H91 135.3 . . ?
O7 Eu1 H91 86.7 . . ?
O8 Eu1 H91 87.8 3_676 . ?
C7 Eu1 H91 177.7 3_576 . ?
O4 N1 C1 118.4(4) . . ?
O4 N1 C5 119.9(4) . . ?
C1 N1 C5 121.7(5) . . ?
P1 O1 Eu1 146.85(18) . . ?
P1 O2 H2A 109.5 . . ?
P1 O3 Eu1 145.14(18) . 2 ?
N1 O4 Eu1 128.4(3) . 2 ?
C7 O5 Eu1 120.2(3) . 3_576 ?
C7 O6 Eu1 119.8(3) . . ?
C8 O7 Eu1 119.2(3) . . ?
C8 O8 Eu1 119.5(3) . 3_676 ?
Eu1 O9 H91 112.4 . . ?
Eu1 O9 H92 121.2 . . ?
H91 O9 H92 126.1 . . ?
H101 O10 H102 110.5 . . ?
H111 O11 H112 105.1 . . ?
H121 O12 H122 90.4 . . ?
O3 P1 O1 114.79(18) . . ?
O3 P1 O2 109.4(2) . . ?
O1 P1 O2 110.37(17) . . ?
O3 P1 C6 109.2(2) . . ?
O1 P1 C6 108.7(2) . . ?
O2 P1 C6 103.8(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2A O8 0.82 1.81 2.616(4) 166.9 3_676
O9 H91 O3 0.76 2.48 2.762(5) 103.8 2_545
O9 H91 O11 0.76 2.49 3.111(12) 138.9 .
O10 H101 O11 0.81 2.32 2.906(11) 130.0 2_655
O10 H101 O2 0.81 2.53 3.179(7) 138.4 2_645
O10 H102 O5 0.88 2.06 2.905(6) 161.0 1_655
O10 H102 O6 0.88 2.67 3.068(5) 108.7 1_655
O11 H112 O1 0.87 2.45 3.082(9) 130.1 2_545
O11 H112 O3 0.87 2.49 3.321(10) 159.6 2_545
O12 H121 O11 0.85 1.82 2.545(18) 142.2 .
O12 H122 O4 0.86 2.30 2.886(15) 125.2 3_575
O12 H122 O5 0.86 2.59 3.220(15) 131.2 2_545

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.923
_refine_diff_density_min         -0.922
_refine_diff_density_rms         0.111
####################################################################### 
# 
# 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_2-Gd
_database_code_depnum_ccdc_archive 'CCDC 1439793'
_audit_update_record             
;
2016-02-01 deposited with the CCDC.
2016-02-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H9 Gd N O9 P, 3(H2 O)'
_chemical_formula_sum            'C8 H15 Gd N O12 P'
_chemical_formula_weight         505.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Gd Gd -0.1653 3.9035 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   9.7306(19)
_cell_length_b                   10.530(2)
_cell_length_c                   16.416(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.13(2)
_cell_angle_gamma                90.00
_cell_volume                     1558.1(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    14478
_cell_measurement_theta_min      3.03
_cell_measurement_theta_max      27.52

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.155
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             980
_exptl_absorpt_coefficient_mu    4.421
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5646
_exptl_absorpt_correction_T_max  0.6190
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            11695
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_sigmaI/netI    0.0266
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.30
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2740
_reflns_number_gt                2659
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'RAPID-AUTO (Rigaku Corporation, 1998)'
_computing_cell_refinement       RAPID-AUTO
_computing_data_reduction        
'CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2002)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXL-97

_refine_special_details          
; 
omit -2 50
ISOR 0.01 O11 O12
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0266P)²+3.4916P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2740
_refine_ls_number_parameters     209
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0261
_refine_ls_R_factor_gt           0.0246
_refine_ls_wR_factor_ref         0.0614
_refine_ls_wR_factor_gt          0.0606
_refine_ls_goodness_of_fit_ref   1.153
_refine_ls_restrained_S_all      1.153
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.3229(5) 1.0539(5) -0.0307(3) 0.0452(12) Uani 1 1 d . . .
H1 H -0.3926 1.1102 -0.0673 0.054 Uiso 1 1 calc R . .
C2 C -0.3579(6) 0.9271(6) -0.0295(4) 0.0575(16) Uani 1 1 d . . .
H2 H -0.4506 0.8972 -0.0661 0.069 Uiso 1 1 calc R . .
C3 C -0.2558(8) 0.8458(6) 0.0257(4) 0.0627(17) Uani 1 1 d . . .
H3 H -0.2798 0.7606 0.0276 0.075 Uiso 1 1 calc R . .
C4 C -0.1183(7) 0.8891(4) 0.0783(3) 0.0479(13) Uani 1 1 d . . .
H4 H -0.0489 0.8332 0.1156 0.057 Uiso 1 1 calc R . .
C5 C -0.0817(5) 1.0171(4) 0.0760(3) 0.0297(9) Uani 1 1 d . . .
C6 C 0.0660(5) 1.0714(4) 0.1280(3) 0.0302(9) Uani 1 1 d . . .
H6A H 0.0903 1.1349 0.0928 0.036 Uiso 1 1 calc R . .
H6B H 0.1398 1.0046 0.1410 0.036 Uiso 1 1 calc R . .
C7 C -0.0715(4) 0.9674(3) 0.4680(2) 0.0200(7) Uani 1 1 d . . .
C8 C 0.5165(4) 0.9399(3) 0.5291(2) 0.0201(7) Uani 1 1 d . . .
Gd1 Gd 0.180219(17) 0.888037(16) 0.393420(10) 0.01644(9) Uani 1 1 d . . .
N1 N -0.1867(4) 1.0962(3) 0.0215(2) 0.0274(7) Uani 1 1 d . . .
O1 O 0.0620(3) 1.0420(3) 0.29066(17) 0.0254(6) Uani 1 1 d . . .
O2 O 0.2371(3) 1.2032(3) 0.26798(19) 0.0345(7) Uani 1 1 d . . .
H2A H 0.2840 1.1730 0.3166 0.052 Uiso 1 1 calc R . .
O3 O -0.0385(3) 1.2463(2) 0.21048(16) 0.0246(6) Uani 1 1 d . . .
O4 O -0.1546(3) 1.2179(3) 0.01707(17) 0.0296(6) Uani 1 1 d . . .
O5 O -0.1857(3) 0.9794(3) 0.48541(18) 0.0279(6) Uani 1 1 d . . .
O6 O -0.0619(3) 0.9090(3) 0.40476(18) 0.0274(6) Uani 1 1 d . . .
O7 O 0.4262(3) 0.8520(3) 0.50717(19) 0.0296(6) Uani 1 1 d . . .
O8 O 0.6373(3) 0.9432(3) 0.59488(17) 0.0267(6) Uani 1 1 d . . .
O9 O 0.3212(4) 0.8160(4) 0.3099(3) 0.0596(11) Uani 1 1 d . . .
H91 H 0.2771 0.7593 0.2723 0.089 Uiso 1 1 d R . .
H92 H 0.3947 0.8610 0.3114 0.089 Uiso 1 1 d R . .
O10 O 0.6036(4) 0.8668(5) 0.3216(3) 0.0759(14) Uani 1 1 d . . .
H101 H 0.6549 0.8715 0.2897 0.114 Uiso 1 1 d R . .
H102 H 0.6435 0.9129 0.3669 0.114 Uiso 1 1 d R . .
O11 O 0.2741(7) 0.5601(8) 0.2665(6) 0.149(3) Uani 1 1 d . . .
H111 H 0.2057 0.5716 0.2861 0.224 Uiso 1 1 d R . .
H112 H 0.2807 0.4852 0.2869 0.224 Uiso 1 1 d R . .
O12 O 0.214(3) 0.681(3) 0.1625(16) 0.463(14) Uani 1 1 d U . .
H121 H 0.3032 0.6896 0.1661 0.694 Uiso 1 1 d R . .
H122 H 0.1792 0.6738 0.1068 0.694 Uiso 1 1 d R . .
P1 P 0.07588(10) 1.14354(9) 0.23021(6) 0.0201(2) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.353(6) . ?
C1 C2 1.381(8) . ?
C1 H1 0.9300 . ?
C2 C3 1.365(9) . ?
C2 H2 0.9300 . ?
C3 C4 1.369(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.398(6) . ?
C4 H4 0.9300 . ?
C5 N1 1.360(5) . ?
C5 C6 1.482(6) . ?
C6 P1 1.811(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 O6 1.240(5) . ?
C7 O5 1.253(5) . ?
C7 C7 1.553(7) 3_576 ?
C8 O7 1.233(5) . ?
C8 O8 1.262(4) . ?
C8 C8 1.546(7) 3_676 ?
Gd1 O3 2.295(3) 2_545 ?
Gd1 O1 2.310(3) . ?
Gd1 O4 2.389(3) 2_545 ?
Gd1 O9 2.399(3) . ?
Gd1 O5 2.414(3) 3_576 ?
Gd1 O6 2.443(3) . ?
Gd1 O7 2.448(3) . ?
Gd1 O8 2.468(3) 3_676 ?
N1 O4 1.328(4) . ?
O1 P1 1.499(3) . ?
O2 P1 1.584(3) . ?
O2 H2A 0.8200 . ?
O3 P1 1.498(3) . ?
O3 Gd1 2.295(3) 2 ?
O4 Gd1 2.389(3) 2 ?
O5 Gd1 2.414(3) 3_576 ?
O8 Gd1 2.468(3) 3_676 ?
O9 H91 0.8500 . ?
O9 H92 0.8500 . ?
O10 H101 0.8500 . ?
O10 H102 0.8501 . ?
O11 H111 0.8500 . ?
O11 H112 0.8500 . ?
O12 H121 0.8500 . ?
O12 H122 0.8500 . ?

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
N1 C1 C2 119.8(5) . . ?
N1 C1 H1 120.1 . . ?
C2 C1 H1 120.1 . . ?
C3 C2 C1 119.6(5) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 120.2(5) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C5 120.2(5) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
N1 C5 C4 118.2(4) . . ?
N1 C5 C6 117.9(4) . . ?
C4 C5 C6 123.9(4) . . ?
C5 C6 P1 113.4(3) . . ?
C5 C6 H6A 108.9 . . ?
P1 C6 H6A 108.9 . . ?
C5 C6 H6B 108.9 . . ?
P1 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
O6 C7 O5 126.4(3) . . ?
O6 C7 C7 117.0(4) . 3_576 ?
O5 C7 C7 116.6(4) . 3_576 ?
O7 C8 O8 127.1(3) . . ?
O7 C8 C8 118.3(4) . 3_676 ?
O8 C8 C8 114.6(4) . 3_676 ?
O3 Gd1 O1 85.37(10) 2_545 . ?
O3 Gd1 O4 78.27(9) 2_545 2_545 ?
O1 Gd1 O4 146.82(9) . 2_545 ?
O3 Gd1 O9 71.48(10) 2_545 . ?
O1 Gd1 O9 92.25(13) . . ?
O4 Gd1 O9 109.21(13) 2_545 . ?
O3 Gd1 O5 144.01(9) 2_545 3_576 ?
O1 Gd1 O5 92.65(10) . 3_576 ?
O4 Gd1 O5 84.37(10) 2_545 3_576 ?
O9 Gd1 O5 144.47(10) . 3_576 ?
O3 Gd1 O6 77.81(9) 2_545 . ?
O1 Gd1 O6 76.27(10) . . ?
O4 Gd1 O6 72.18(10) 2_545 . ?
O9 Gd1 O6 147.99(10) . . ?
O5 Gd1 O6 66.89(9) 3_576 . ?
O3 Gd1 O7 127.38(10) 2_545 . ?
O1 Gd1 O7 137.80(9) . . ?
O4 Gd1 O7 73.32(9) 2_545 . ?
O9 Gd1 O7 77.39(12) . . ?
O5 Gd1 O7 75.47(10) 3_576 . ?
O6 Gd1 O7 130.53(10) . . ?
O3 Gd1 O8 137.68(9) 2_545 3_676 ?
O1 Gd1 O8 72.37(9) . 3_676 ?
O4 Gd1 O8 136.96(9) 2_545 3_676 ?
O9 Gd1 O8 73.90(11) . 3_676 ?
O5 Gd1 O8 74.19(9) 3_576 3_676 ?
O6 Gd1 O8 127.97(9) . 3_676 ?
O7 Gd1 O8 65.44(9) . 3_676 ?
O4 N1 C1 118.5(4) . . ?
O4 N1 C5 119.5(3) . . ?
C1 N1 C5 121.9(4) . . ?
P1 O1 Gd1 147.10(16) . . ?
P1 O2 H2A 109.5 . . ?
P1 O3 Gd1 145.09(16) . 2 ?
N1 O4 Gd1 127.6(2) . 2 ?
C7 O5 Gd1 120.0(2) . 3_576 ?
C7 O6 Gd1 119.2(2) . . ?
C8 O7 Gd1 119.4(2) . . ?
C8 O8 Gd1 119.8(2) . 3_676 ?
Gd1 O9 H91 113.3 . . ?
Gd1 O9 H92 117.5 . . ?
H91 O9 H92 127.1 . . ?
H101 O10 H102 109.0 . . ?
H111 O11 H112 86.4 . . ?
H121 O12 H122 94.0 . . ?
O3 P1 O1 114.40(16) . . ?
O3 P1 O2 110.14(17) . . ?
O1 P1 O2 110.29(15) . . ?
O3 P1 C6 109.08(17) . . ?
O1 P1 C6 109.14(19) . . ?
O2 P1 C6 103.19(19) . . ?

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
O12 H122 O5 0.85 2.56 3.16(3) 128.0 2_545
O12 H122 O4 0.85 2.26 2.98(2) 141.9 3_575
O11 H111 O3 0.85 2.47 3.146(7) 137.0 2_545
O11 H111 O1 0.85 2.45 3.050(7) 128.3 2_545
O10 H102 O6 0.85 2.70 3.050(5) 106.7 1_655
O10 H102 O5 0.85 2.14 2.947(5) 157.3 1_655
O10 H101 O2 0.85 2.43 3.041(5) 129.6 2_645
O10 H101 O11 0.85 2.40 2.990(8) 127.3 2_655
O9 H91 O11 0.85 2.10 2.781(9) 136.9 .
O9 H91 O3 0.85 2.45 2.743(4) 101.4 2_545
O2 H2A O8 0.82 1.83 2.620(4) 160.8 3_676

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.981
_refine_diff_density_min         -0.763
_refine_diff_density_rms         0.131
####################################################################### 
# 
# 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_3-Tb
_database_code_depnum_ccdc_archive 'CCDC 1439794'
_audit_update_record             
;
2016-02-01 deposited with the CCDC.
2016-02-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H9 N O9 P Tb, 3(H2 O)'
_chemical_formula_sum            'C8 H15 N O12 P Tb'
_chemical_formula_weight         507.10

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'
Tb Tb -0.1723 4.1537 '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'
P P 0.1023 0.0942 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   9.7284(3)
_cell_length_b                   10.4717(3)
_cell_length_c                   16.4594(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.511(3)
_cell_angle_gamma                90.00
_cell_volume                     1549.01(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3708
_cell_measurement_theta_min      3.3047
_cell_measurement_theta_max      29.1392

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.174
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             984
_exptl_absorpt_coefficient_mu    4.731
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4636
_exptl_absorpt_correction_T_max  0.5019
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1954
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6094
_diffrn_reflns_av_R_equivalents  0.0147
_diffrn_reflns_av_sigmaI/netI    0.0216
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.31
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2719
_reflns_number_gt                2544
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
omit -2 50
ISOR 0.01 O11 O12
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0244P)²+3.7332P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2719
_refine_ls_number_parameters     209
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0243
_refine_ls_R_factor_gt           0.0220
_refine_ls_wR_factor_ref         0.0552
_refine_ls_wR_factor_gt          0.0541
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.127
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.3216(5) 1.0573(6) -0.0309(4) 0.0414(13) Uani 1 1 d . . .
H1 H -0.3913 1.1140 -0.0677 0.050 Uiso 1 1 calc R . .
C2 C -0.3566(7) 0.9298(7) -0.0301(4) 0.0556(17) Uani 1 1 d . . .
H2 H -0.4501 0.8999 -0.0663 0.067 Uiso 1 1 calc R . .
C3 C -0.2536(8) 0.8484(6) 0.0238(4) 0.0583(18) Uani 1 1 d . . .
H3 H -0.2763 0.7624 0.0250 0.070 Uiso 1 1 calc R . .
C4 C -0.1147(8) 0.8934(5) 0.0770(4) 0.0469(14) Uani 1 1 d . . .
H4 H -0.0444 0.8372 0.1139 0.056 Uiso 1 1 calc R . .
C5 C -0.0793(5) 1.0206(5) 0.0760(3) 0.0283(10) Uani 1 1 d . . .
C6 C 0.0677(5) 1.0756(5) 0.1297(3) 0.0297(11) Uani 1 1 d . . .
H6A H 0.0929 1.1397 0.0951 0.036 Uiso 1 1 calc R . .
H6B H 0.1421 1.0087 0.1436 0.036 Uiso 1 1 calc R . .
C7 C -0.0716(4) 0.9683(4) 0.4673(3) 0.0192(9) Uani 1 1 d . . .
C8 C 0.5177(4) 0.9387(4) 0.5274(3) 0.0174(8) Uani 1 1 d . . .
Tb1 Tb 0.178729(19) 0.892522(18) 0.393138(11) 0.01450(8) Uani 1 1 d . . .
N1 N -0.1854(4) 1.0994(4) 0.0222(2) 0.0256(8) Uani 1 1 d . . .
O1 O 0.0600(3) 1.0452(3) 0.29084(18) 0.0232(6) Uani 1 1 d . . .
O2 O 0.2349(3) 1.2092(3) 0.2710(2) 0.0331(8) Uani 1 1 d . . .
H2A H 0.2867 1.1691 0.3148 0.050 Uiso 1 1 calc R . .
O3 O -0.0404(3) 1.2501(3) 0.20993(18) 0.0236(6) Uani 1 1 d . . .
O4 O -0.1542(3) 1.2221(3) 0.01776(19) 0.0273(7) Uani 1 1 d . . .
O5 O -0.1857(3) 0.9798(3) 0.48470(19) 0.0262(7) Uani 1 1 d . . .
O6 O -0.0626(3) 0.9123(3) 0.40331(19) 0.0250(7) Uani 1 1 d . . .
O7 O 0.4238(3) 0.8513(3) 0.5052(2) 0.0277(7) Uani 1 1 d . . .
O8 O 0.6407(3) 0.9367(3) 0.59170(18) 0.0241(7) Uani 1 1 d . . .
O9 O 0.3165(4) 0.8297(5) 0.3081(3) 0.0598(13) Uani 1 1 d . . .
H91 H 0.2797 0.7751 0.2770 0.090 Uiso 1 1 d R . .
H92 H 0.3945 0.8707 0.3106 0.090 Uiso 1 1 d R . .
O10 O 0.5982(5) 0.8769(7) 0.3231(4) 0.123(3) Uani 1 1 d . . .
H101 H 0.6465 0.8737 0.2929 0.184 Uiso 1 1 d R . .
H102 H 0.6452 0.9203 0.3709 0.184 Uiso 1 1 d R . .
O11 O 0.2821(10) 0.5349(12) 0.2801(6) 0.193(4) Uani 1 1 d U . .
H111 H 0.2854 0.4598 0.3034 0.289 Uiso 1 1 d R . .
H112 H 0.2090 0.5736 0.2872 0.289 Uiso 1 1 d R . .
O12 O 0.2379(15) 0.6983(14) 0.1623(8) 0.258(6) Uani 1 1 d U . .
H121 H 0.2374 0.6229 0.1806 0.387 Uiso 1 1 d R . .
H122 H 0.1788 0.6763 0.1108 0.387 Uiso 1 1 d R . .
P1 P 0.07489(11) 1.14779(11) 0.23106(7) 0.0189(2) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.351(6) . ?
C1 C2 1.380(9) . ?
C1 H1 0.9300 . ?
C2 C3 1.355(10) . ?
C2 H2 0.9300 . ?
C3 C4 1.381(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(7) . ?
C4 H4 0.9300 . ?
C5 N1 1.353(6) . ?
C5 C6 1.480(7) . ?
C6 P1 1.808(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 O6 1.237(5) . ?
C7 O5 1.254(5) . ?
C7 C7 1.547(8) 3_576 ?
C8 O7 1.245(5) . ?
C8 O8 1.258(5) . ?
C8 C8 1.531(8) 3_676 ?
Tb1 O3 2.273(3) 2_545 ?
Tb1 O1 2.289(3) . ?
Tb1 O9 2.372(3) . ?
Tb1 O4 2.379(3) 2_545 ?
Tb1 O5 2.394(3) 3_576 ?
Tb1 O6 2.426(3) . ?
Tb1 O7 2.430(3) . ?
Tb1 O8 2.452(3) 3_676 ?
N1 O4 1.329(5) . ?
O1 P1 1.501(3) . ?
O2 P1 1.577(3) . ?
O2 H2A 0.8200 . ?
O3 P1 1.493(3) . ?
O3 Tb1 2.273(3) 2 ?
O4 Tb1 2.379(3) 2 ?
O5 Tb1 2.394(3) 3_576 ?
O8 Tb1 2.452(3) 3_676 ?
O9 H91 0.7596 . ?
O9 H92 0.8582 . ?
O10 H101 0.8037 . ?
O10 H102 0.8709 . ?
O11 H111 0.8711 . ?
O11 H112 0.8643 . ?
O12 H121 0.8459 . ?
O12 H122 0.8547 . ?

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
N1 C1 C2 119.6(6) . . ?
N1 C1 H1 120.2 . . ?
C2 C1 H1 120.2 . . ?
C3 C2 C1 119.4(6) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 C4 120.0(6) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 120.7(6) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
N1 C5 C4 117.8(5) . . ?
N1 C5 C6 118.3(4) . . ?
C4 C5 C6 124.0(5) . . ?
C5 C6 P1 113.6(3) . . ?
C5 C6 H6A 108.8 . . ?
P1 C6 H6A 108.8 . . ?
C5 C6 H6B 108.8 . . ?
P1 C6 H6B 108.8 . . ?
H6A C6 H6B 107.7 . . ?
O6 C7 O5 126.7(4) . . ?
O6 C7 C7 117.3(4) . 3_576 ?
O5 C7 C7 116.0(4) . 3_576 ?
O7 C8 O8 126.2(4) . . ?
O7 C8 C8 118.0(4) . 3_676 ?
O8 C8 C8 115.9(4) . 3_676 ?
O3 Tb1 O1 85.49(11) 2_545 . ?
O3 Tb1 O9 71.62(11) 2_545 . ?
O1 Tb1 O9 89.99(14) . . ?
O3 Tb1 O4 78.32(10) 2_545 2_545 ?
O1 Tb1 O4 146.73(10) . 2_545 ?
O9 Tb1 O4 111.63(14) . 2_545 ?
O3 Tb1 O5 144.25(10) 2_545 3_576 ?
O1 Tb1 O5 94.11(11) . 3_576 ?
O9 Tb1 O5 144.09(11) . 3_576 ?
O4 Tb1 O5 83.01(11) 2_545 3_576 ?
O3 Tb1 O6 78.19(10) 2_545 . ?
O1 Tb1 O6 76.21(10) . . ?
O9 Tb1 O6 147.69(11) . . ?
O4 Tb1 O6 72.15(11) 2_545 . ?
O5 Tb1 O6 67.11(9) 3_576 . ?
O3 Tb1 O7 125.36(11) 2_545 . ?
O1 Tb1 O7 139.00(10) . . ?
O9 Tb1 O7 77.67(13) . . ?
O4 Tb1 O7 72.54(10) 2_545 . ?
O5 Tb1 O7 75.99(11) 3_576 . ?
O6 Tb1 O7 131.09(10) . . ?
O3 Tb1 O8 138.68(10) 2_545 3_676 ?
O1 Tb1 O8 72.87(10) . 3_676 ?
O9 Tb1 O8 73.58(12) . 3_676 ?
O4 Tb1 O8 136.17(10) 2_545 3_676 ?
O5 Tb1 O8 73.65(10) 3_576 3_676 ?
O6 Tb1 O8 127.26(10) . 3_676 ?
O7 Tb1 O8 66.14(10) . 3_676 ?
O4 N1 C1 117.9(4) . . ?
O4 N1 C5 119.5(4) . . ?
C1 N1 C5 122.5(4) . . ?
P1 O1 Tb1 146.52(17) . . ?
P1 O2 H2A 109.5 . . ?
P1 O3 Tb1 145.32(17) . 2 ?
N1 O4 Tb1 127.8(2) . 2 ?
C7 O5 Tb1 120.2(3) . 3_576 ?
C7 O6 Tb1 119.0(2) . . ?
C8 O7 Tb1 119.3(3) . . ?
C8 O8 Tb1 119.2(3) . 3_676 ?
Tb1 O9 H91 112.3 . . ?
Tb1 O9 H92 121.5 . . ?
H91 O9 H92 126.0 . . ?
H101 O10 H102 110.5 . . ?
H111 O11 H112 104.9 . . ?
H121 O12 H122 90.5 . . ?
O3 P1 O1 114.44(17) . . ?
O3 P1 O2 109.76(19) . . ?
O1 P1 O2 110.27(16) . . ?
O3 P1 C6 108.96(19) . . ?
O1 P1 C6 109.1(2) . . ?
O2 P1 C6 103.8(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2A O8 0.82 1.81 2.610(4) 166.4 3_676
O12 H122 O4 0.85 2.30 2.880(13) 125.7 3_575
O12 H121 O11 0.85 1.78 2.496(17) 141.0 .
O11 H112 O3 0.86 2.48 3.306(10) 159.2 2_545
O11 H112 O1 0.86 2.45 3.078(9) 129.8 2_545
O10 H102 O5 0.87 2.06 2.894(6) 160.0 1_655
O10 H101 O2 0.80 2.52 3.169(7) 139.2 2_645
O10 H101 O11 0.80 2.33 2.914(11) 130.4 2_655
O9 H91 O11 0.76 2.52 3.120(12) 137.8 .
O9 H91 O12 0.76 1.95 2.614(12) 146.5 .

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.861
_refine_diff_density_min         -0.868
_refine_diff_density_rms         0.107
####################################################################### 
# 
# 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_4-Dy
_database_code_depnum_ccdc_archive 'CCDC 1439795'
_audit_update_record             
;
2016-02-01 deposited with the CCDC.
2016-02-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H9 Dy N O9 P, 3(H2 O)'
_chemical_formula_sum            'C8 H15 Dy N O12 P'
_chemical_formula_weight         510.68

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Dy Dy -0.1892 4.4098 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   9.7192(2)
_cell_length_b                   10.4517(2)
_cell_length_c                   16.4217(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.580(2)
_cell_angle_gamma                90.00
_cell_volume                     1540.28(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4029
_cell_measurement_theta_min      2.9858
_cell_measurement_theta_max      29.0701

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.202
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             988
_exptl_absorpt_coefficient_mu    5.018
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4188
_exptl_absorpt_correction_T_max  0.4620
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1954
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6207
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_av_sigmaI/netI    0.0284
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.99
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2704
_reflns_number_gt                2512
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
omit -2 50
ISOR 0.01 O11 O12
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0282P)²+3.7787P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2704
_refine_ls_number_parameters     209
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0264
_refine_ls_R_factor_gt           0.0239
_refine_ls_wR_factor_ref         0.0618
_refine_ls_wR_factor_gt          0.0605
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.096
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.3210(6) 1.0598(6) -0.0315(4) 0.0421(14) Uani 1 1 d . . .
H1 H -0.3904 1.1169 -0.0684 0.051 Uiso 1 1 calc R . .
C2 C -0.3580(8) 0.9327(7) -0.0315(5) 0.0553(19) Uani 1 1 d . . .
H2 H -0.4517 0.9033 -0.0681 0.066 Uiso 1 1 calc R . .
C3 C -0.2536(9) 0.8502(7) 0.0234(5) 0.060(2) Uani 1 1 d . . .
H3 H -0.2762 0.7639 0.0243 0.072 Uiso 1 1 calc R . .
C4 C -0.1168(9) 0.8949(5) 0.0766(4) 0.0486(17) Uani 1 1 d . . .
H4 H -0.0469 0.8384 0.1139 0.058 Uiso 1 1 calc R . .
C5 C -0.0799(6) 1.0224(5) 0.0761(3) 0.0274(11) Uani 1 1 d . . .
C6 C 0.0678(6) 1.0767(5) 0.1298(3) 0.0295(11) Uani 1 1 d . . .
H6A H 0.0936 1.1404 0.0951 0.035 Uiso 1 1 calc R . .
H6B H 0.1418 1.0091 0.1439 0.035 Uiso 1 1 calc R . .
C7 C -0.0722(5) 0.9687(4) 0.4671(3) 0.0190(9) Uani 1 1 d . . .
C8 C 0.5172(5) 0.9382(4) 0.5273(3) 0.0182(9) Uani 1 1 d . . .
Dy1 Dy 0.17842(2) 0.894285(19) 0.393023(12) 0.01456(9) Uani 1 1 d . . .
N1 N -0.1857(5) 1.1020(4) 0.0214(3) 0.0258(9) Uani 1 1 d . . .
O1 O 0.0603(3) 1.0476(3) 0.2919(2) 0.0228(7) Uani 1 1 d . . .
O2 O 0.2350(4) 1.2111(4) 0.2709(2) 0.0337(9) Uani 1 1 d . . .
H2A H 0.2872 1.1707 0.3147 0.051 Uiso 1 1 calc R . .
O3 O -0.0405(3) 1.2519(3) 0.2100(2) 0.0232(7) Uani 1 1 d . . .
O4 O -0.1536(4) 1.2249(3) 0.0177(2) 0.0269(7) Uani 1 1 d . . .
O5 O -0.1860(3) 0.9794(3) 0.4847(2) 0.0252(7) Uani 1 1 d . . .
O6 O -0.0633(3) 0.9136(3) 0.4024(2) 0.0245(7) Uani 1 1 d . . .
O7 O 0.4226(3) 0.8512(3) 0.5044(2) 0.0268(8) Uani 1 1 d . . .
O8 O 0.6411(3) 0.9352(3) 0.5911(2) 0.0243(7) Uani 1 1 d . . .
O9 O 0.3155(4) 0.8316(5) 0.3079(3) 0.0567(13) Uani 1 1 d . . .
H91 H 0.2787 0.7770 0.2768 0.085 Uiso 1 1 d R . .
H92 H 0.3934 0.8726 0.3104 0.085 Uiso 1 1 d R . .
O10 O 0.5975(6) 0.8772(7) 0.3225(4) 0.116(3) Uani 1 1 d . . .
H101 H 0.6458 0.8739 0.2923 0.174 Uiso 1 1 d R . .
H102 H 0.6445 0.9205 0.3703 0.174 Uiso 1 1 d R . .
O11 O 0.2807(11) 0.5384(12) 0.2789(8) 0.201(5) Uani 1 1 d U . .
H111 H 0.2840 0.4632 0.3022 0.302 Uiso 1 1 d R . .
H112 H 0.2076 0.5771 0.2860 0.302 Uiso 1 1 d R . .
O12 O 0.2310(15) 0.6982(14) 0.1620(8) 0.244(6) Uani 1 1 d U . .
H121 H 0.2305 0.6228 0.1803 0.366 Uiso 1 1 d R . .
H122 H 0.1718 0.6762 0.1105 0.366 Uiso 1 1 d R . .
P1 P 0.07480(13) 1.14983(12) 0.23131(7) 0.0188(2) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.342(7) . ?
C1 C2 1.375(9) . ?
C1 H1 0.9300 . ?
C2 C3 1.373(11) . ?
C2 H2 0.9300 . ?
C3 C4 1.363(10) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(7) . ?
C4 H4 0.9300 . ?
C5 N1 1.359(6) . ?
C5 C6 1.479(7) . ?
C6 P1 1.811(5) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 O6 1.240(5) . ?
C7 O5 1.252(5) . ?
C7 C7 1.550(8) 3_576 ?
C8 O7 1.244(6) . ?
C8 O8 1.256(5) . ?
C8 C8 1.535(9) 3_676 ?
Dy1 O3 2.265(3) 2_545 ?
Dy1 O1 2.276(3) . ?
Dy1 O9 2.363(4) . ?
Dy1 O4 2.370(3) 2_545 ?
Dy1 O5 2.380(3) 3_576 ?
Dy1 O7 2.418(3) . ?
Dy1 O6 2.421(3) . ?
Dy1 O8 2.443(3) 3_676 ?
N1 O4 1.329(5) . ?
O1 P1 1.503(3) . ?
O2 P1 1.575(3) . ?
O2 H2A 0.8200 . ?
O3 P1 1.489(3) . ?
O3 Dy1 2.265(3) 2 ?
O4 Dy1 2.370(3) 2 ?
O5 Dy1 2.380(3) 3_576 ?
O8 Dy1 2.443(3) 3_676 ?
O9 H91 0.7578 . ?
O9 H92 0.8572 . ?
O10 H101 0.8027 . ?
O10 H102 0.8686 . ?
O11 H111 0.8694 . ?
O11 H112 0.8634 . ?
O12 H121 0.8442 . ?
O12 H122 0.8523 . ?

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
N1 C1 C2 120.6(6) . . ?
N1 C1 H1 119.7 . . ?
C2 C1 H1 119.7 . . ?
C3 C2 C1 118.6(6) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C4 C3 C2 119.9(6) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 121.2(7) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
N1 C5 C4 117.6(5) . . ?
N1 C5 C6 118.3(4) . . ?
C4 C5 C6 124.1(5) . . ?
C5 C6 P1 113.3(3) . . ?
C5 C6 H6A 108.9 . . ?
P1 C6 H6A 108.9 . . ?
C5 C6 H6B 108.9 . . ?
P1 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
O6 C7 O5 126.8(4) . . ?
O6 C7 C7 116.8(5) . 3_576 ?
O5 C7 C7 116.4(5) . 3_576 ?
O7 C8 O8 126.5(4) . . ?
O7 C8 C8 117.9(5) . 3_676 ?
O8 C8 C8 115.6(5) . 3_676 ?
O3 Dy1 O1 85.96(12) 2_545 . ?
O3 Dy1 O9 71.50(12) 2_545 . ?
O1 Dy1 O9 90.27(15) . . ?
O3 Dy1 O4 78.44(11) 2_545 2_545 ?
O1 Dy1 O4 146.60(11) . 2_545 ?
O9 Dy1 O4 111.93(15) . 2_545 ?
O3 Dy1 O5 144.31(11) 2_545 3_576 ?
O1 Dy1 O5 93.93(12) . 3_576 ?
O9 Dy1 O5 144.13(12) . 3_576 ?
O4 Dy1 O5 82.53(11) 2_545 3_576 ?
O3 Dy1 O7 124.75(11) 2_545 . ?
O1 Dy1 O7 139.16(11) . . ?
O9 Dy1 O7 77.47(14) . . ?
O4 Dy1 O7 72.35(11) 2_545 . ?
O5 Dy1 O7 76.21(11) 3_576 . ?
O3 Dy1 O6 77.98(11) 2_545 . ?
O1 Dy1 O6 75.97(11) . . ?
O9 Dy1 O6 147.32(12) . . ?
O4 Dy1 O6 72.00(12) 2_545 . ?
O5 Dy1 O6 67.48(10) 3_576 . ?
O7 Dy1 O6 131.47(11) . . ?
O3 Dy1 O8 138.90(11) 2_545 3_676 ?
O1 Dy1 O8 72.83(11) . 3_676 ?
O9 Dy1 O8 73.78(13) . 3_676 ?
O4 Dy1 O8 135.93(11) 2_545 3_676 ?
O5 Dy1 O8 73.55(11) 3_576 3_676 ?
O7 Dy1 O8 66.35(10) . 3_676 ?
O6 Dy1 O8 127.36(11) . 3_676 ?
O4 N1 C1 118.5(5) . . ?
O4 N1 C5 119.4(4) . . ?
C1 N1 C5 122.1(5) . . ?
P1 O1 Dy1 146.53(19) . . ?
P1 O2 H2A 109.5 . . ?
P1 O3 Dy1 145.36(18) . 2 ?
N1 O4 Dy1 127.7(3) . 2 ?
C7 O5 Dy1 120.1(3) . 3_576 ?
C7 O6 Dy1 118.8(3) . . ?
C8 O7 Dy1 119.3(3) . . ?
C8 O8 Dy1 119.3(3) . 3_676 ?
Dy1 O9 H91 112.3 . . ?
Dy1 O9 H92 121.5 . . ?
H91 O9 H92 126.0 . . ?
H101 O10 H102 110.5 . . ?
H111 O11 H112 104.9 . . ?
H121 O12 H122 90.5 . . ?
O3 P1 O1 114.30(18) . . ?
O3 P1 O2 110.0(2) . . ?
O1 P1 O2 110.17(18) . . ?
O3 P1 C6 109.1(2) . . ?
O1 P1 C6 109.2(2) . . ?
O2 P1 C6 103.5(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2A O8 0.82 1.81 2.613(4) 165.9 3_676
O9 H91 O3 0.76 2.42 2.705(5) 104.0 2_545
O9 H91 O11 0.76 2.49 3.101(13) 138.1 .
O10 H101 O11 0.80 2.34 2.919(12) 129.8 2_655
O10 H101 O2 0.80 2.50 3.152(7) 139.4 2_645
O10 H102 O5 0.87 2.06 2.892(7) 159.9 1_655
O11 H112 O1 0.86 2.44 3.064(11) 129.7 2_545
O11 H112 O3 0.86 2.46 3.285(11) 159.5 2_545
O12 H121 O11 0.84 1.74 2.448(17) 140.0 .
O12 H122 O4 0.85 2.29 2.867(13) 125.2 3_575

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.938
_refine_diff_density_min         -0.990
_refine_diff_density_rms         0.118
####################################################################### 
# 
# 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_5-Ho
_database_code_depnum_ccdc_archive 'CCDC 1439796'
_audit_update_record             
;
2016-02-01 deposited with the CCDC.
2016-02-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H9 Ho N O9 P, 3(H2 O)'
_chemical_formula_sum            'C8 H15 Ho N O12 P'
_chemical_formula_weight         513.11

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ho Ho -0.2175 4.6783 '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'
P P 0.1023 0.0942 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   9.7216(3)
_cell_length_b                   10.4273(3)
_cell_length_c                   16.4046(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.678(3)
_cell_angle_gamma                90.00
_cell_volume                     1534.37(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3120
_cell_measurement_theta_min      2.8972
_cell_measurement_theta_max      29.0508

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.221
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             992
_exptl_absorpt_coefficient_mu    5.324
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4577
_exptl_absorpt_correction_T_max  0.5103
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1954
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6067
_diffrn_reflns_av_R_equivalents  0.0187
_diffrn_reflns_av_sigmaI/netI    0.0257
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.90
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2697
_reflns_number_gt                2518
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
omit -2 50
ISOR 0.01 O11 O12
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0260P)²+4.7288P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2697
_refine_ls_number_parameters     209
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0251
_refine_ls_R_factor_gt           0.0228
_refine_ls_wR_factor_ref         0.0568
_refine_ls_wR_factor_gt          0.0552
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.048
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.3212(6) 1.0615(6) -0.0324(4) 0.0414(14) Uani 1 1 d . . .
H1 H -0.3908 1.1184 -0.0697 0.050 Uiso 1 1 calc R . .
C2 C -0.3570(7) 0.9342(7) -0.0321(5) 0.0535(18) Uani 1 1 d . . .
H2 H -0.4506 0.9045 -0.0688 0.064 Uiso 1 1 calc R . .
C3 C -0.2539(9) 0.8517(7) 0.0226(5) 0.059(2) Uani 1 1 d . . .
H3 H -0.2772 0.7654 0.0233 0.071 Uiso 1 1 calc R . .
C4 C -0.1158(8) 0.8958(5) 0.0767(4) 0.0482(16) Uani 1 1 d . . .
H4 H -0.0461 0.8391 0.1142 0.058 Uiso 1 1 calc R . .
C5 C -0.0792(6) 1.0240(5) 0.0760(3) 0.0280(11) Uani 1 1 d . . .
C6 C 0.0689(5) 1.0790(5) 0.1305(3) 0.0293(11) Uani 1 1 d . . .
H6A H 0.0949 1.1430 0.0960 0.035 Uiso 1 1 calc R . .
H6B H 0.1432 1.0115 0.1449 0.035 Uiso 1 1 calc R . .
C7 C -0.0718(5) 0.9690(4) 0.4670(3) 0.0191(9) Uani 1 1 d . . .
C8 C 0.5172(5) 0.9375(4) 0.5266(3) 0.0169(9) Uani 1 1 d . . .
Ho1 Ho 0.17796(2) 0.896396(19) 0.392929(12) 0.01447(8) Uani 1 1 d . . .
N1 N -0.1856(4) 1.1044(4) 0.0214(3) 0.0255(9) Uani 1 1 d . . .
O1 O 0.0606(3) 1.0497(3) 0.2924(2) 0.0228(7) Uani 1 1 d . . .
O2 O 0.2348(4) 1.2138(4) 0.2719(2) 0.0348(9) Uani 1 1 d . . .
H2A H 0.2868 1.1737 0.3160 0.052 Uiso 1 1 calc R . .
O3 O -0.0418(3) 1.2538(3) 0.20991(19) 0.0248(7) Uani 1 1 d . . .
O4 O -0.1527(3) 1.2275(3) 0.0178(2) 0.0261(7) Uani 1 1 d . . .
O5 O -0.1860(3) 0.9791(3) 0.4842(2) 0.0254(7) Uani 1 1 d . . .
O6 O -0.0632(3) 0.9154(3) 0.4017(2) 0.0241(7) Uani 1 1 d . . .
O7 O 0.4217(3) 0.8511(3) 0.5033(2) 0.0262(7) Uani 1 1 d . . .
O8 O 0.6416(3) 0.9332(3) 0.5901(2) 0.0232(7) Uani 1 1 d . . .
O9 O 0.3126(4) 0.8376(5) 0.3067(3) 0.0552(13) Uani 1 1 d . . .
H91 H 0.2833 0.7685 0.2778 0.083 Uiso 1 1 d R . .
H92 H 0.3981 0.8640 0.3113 0.083 Uiso 1 1 d R . .
O10 O 0.5942(6) 0.8824(8) 0.3229(4) 0.136(4) Uani 1 1 d . . .
H101 H 0.6487 0.8715 0.2934 0.205 Uiso 1 1 d R . .
H102 H 0.6475 0.9181 0.3714 0.205 Uiso 1 1 d R . .
O11 O 0.2833(12) 0.5323(13) 0.2829(7) 0.214(5) Uani 1 1 d U . .
H111 H 0.2844 0.4565 0.3021 0.321 Uiso 1 1 d R . .
H112 H 0.2082 0.5703 0.2861 0.321 Uiso 1 1 d R . .
O12 O 0.2313(13) 0.7010(12) 0.1627(7) 0.219(5) Uani 1 1 d U . .
H121 H 0.2440 0.6232 0.1795 0.329 Uiso 1 1 d R . .
H122 H 0.1854 0.6766 0.1096 0.329 Uiso 1 1 d R . .
P1 P 0.07448(12) 1.15183(12) 0.23178(7) 0.0195(2) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.349(7) . ?
C1 C2 1.373(9) . ?
C1 H1 0.9300 . ?
C2 C3 1.362(10) . ?
C2 H2 0.9300 . ?
C3 C4 1.372(10) . ?
C3 H3 0.9300 . ?
C4 C5 1.384(7) . ?
C4 H4 0.9300 . ?
C5 N1 1.365(6) . ?
C5 C6 1.485(7) . ?
C6 P1 1.808(5) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 O6 1.240(5) . ?
C7 O5 1.251(5) . ?
C7 C7 1.540(8) 3_576 ?
C8 O7 1.243(5) . ?
C8 O8 1.257(5) . ?
C8 C8 1.531(9) 3_676 ?
Ho1 O3 2.255(3) 2_545 ?
Ho1 O1 2.264(3) . ?
Ho1 O9 2.349(3) . ?
Ho1 O4 2.363(3) 2_545 ?
Ho1 O5 2.373(3) 3_576 ?
Ho1 O7 2.410(3) . ?
Ho1 O6 2.412(3) . ?
Ho1 O8 2.436(3) 3_676 ?
N1 O4 1.330(5) . ?
O1 P1 1.498(3) . ?
O2 P1 1.577(3) . ?
O2 H2A 0.8200 . ?
O3 P1 1.492(3) . ?
O3 Ho1 2.255(3) 2 ?
O4 Ho1 2.363(3) 2 ?
O5 Ho1 2.373(3) 3_576 ?
O8 Ho1 2.436(3) 3_676 ?
O9 H91 0.8499 . ?
O9 H92 0.8500 . ?
O10 H101 0.8501 . ?
O10 H102 0.8501 . ?
O11 H111 0.8500 . ?
O11 H112 0.8500 . ?
O12 H121 0.8500 . ?
O12 H122 0.8500 . ?

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
N1 C1 C2 120.2(6) . . ?
N1 C1 H1 119.9 . . ?
C2 C1 H1 119.9 . . ?
C3 C2 C1 119.3(6) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 C4 120.2(6) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C5 120.6(6) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
N1 C5 C4 117.8(5) . . ?
N1 C5 C6 118.2(4) . . ?
C4 C5 C6 124.0(5) . . ?
C5 C6 P1 113.2(3) . . ?
C5 C6 H6A 108.9 . . ?
P1 C6 H6A 108.9 . . ?
C5 C6 H6B 108.9 . . ?
P1 C6 H6B 108.9 . . ?
H6A C6 H6B 107.8 . . ?
O6 C7 O5 126.4(4) . . ?
O6 C7 C7 116.8(5) . 3_576 ?
O5 C7 C7 116.7(5) . 3_576 ?
O7 C8 O8 126.5(4) . . ?
O7 C8 C8 117.9(4) . 3_676 ?
O8 C8 C8 115.6(5) . 3_676 ?
O3 Ho1 O1 86.27(12) 2_545 . ?
O3 Ho1 O9 71.36(12) 2_545 . ?
O1 Ho1 O9 89.26(15) . . ?
O3 Ho1 O4 78.54(11) 2_545 2_545 ?
O1 Ho1 O4 146.51(11) . 2_545 ?
O9 Ho1 O4 113.21(15) . 2_545 ?
O3 Ho1 O5 144.44(10) 2_545 3_576 ?
O1 Ho1 O5 94.27(12) . 3_576 ?
O9 Ho1 O5 144.14(12) . 3_576 ?
O4 Ho1 O5 81.87(11) 2_545 3_576 ?
O3 Ho1 O7 123.82(11) 2_545 . ?
O1 Ho1 O7 139.37(11) . . ?
O9 Ho1 O7 77.67(13) . . ?
O4 Ho1 O7 72.27(11) 2_545 . ?
O5 Ho1 O7 76.59(11) 3_576 . ?
O3 Ho1 O6 78.16(11) 2_545 . ?
O1 Ho1 O6 75.93(11) . . ?
O9 Ho1 O6 146.88(12) . . ?
O4 Ho1 O6 71.85(11) 2_545 . ?
O5 Ho1 O6 67.61(10) 3_576 . ?
O7 Ho1 O6 131.93(11) . . ?
O3 Ho1 O8 139.05(11) 2_545 3_676 ?
O1 Ho1 O8 72.93(10) . 3_676 ?
O9 Ho1 O8 73.45(13) . 3_676 ?
O4 Ho1 O8 135.65(10) 2_545 3_676 ?
O5 Ho1 O8 73.59(11) 3_576 3_676 ?
O7 Ho1 O8 66.49(10) . 3_676 ?
O6 Ho1 O8 127.37(11) . 3_676 ?
O4 N1 C1 118.9(5) . . ?
O4 N1 C5 119.2(4) . . ?
C1 N1 C5 121.9(5) . . ?
P1 O1 Ho1 146.74(18) . . ?
P1 O2 H2A 109.5 . . ?
P1 O3 Ho1 145.27(18) . 2 ?
N1 O4 Ho1 127.4(3) . 2 ?
C7 O5 Ho1 119.7(3) . 3_576 ?
C7 O6 Ho1 118.6(3) . . ?
C8 O7 Ho1 119.4(3) . . ?
C8 O8 Ho1 119.3(3) . 3_676 ?
Ho1 O9 H91 114.4 . . ?
Ho1 O9 H92 127.9 . . ?
H91 O9 H92 115.5 . . ?
H101 O10 H102 107.6 . . ?
H111 O11 H112 107.4 . . ?
H121 O12 H122 90.0 . . ?
O3 P1 O1 114.37(18) . . ?
O3 P1 O2 110.1(2) . . ?
O1 P1 O2 109.98(18) . . ?
O3 P1 C6 109.1(2) . . ?
O1 P1 C6 109.4(2) . . ?
O2 P1 C6 103.3(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O9 H91 O3 0.85 2.44 2.687(5) 97.7 2_545
O9 H91 O11 0.85 2.46 3.206(14) 146.4 .
O10 H101 O11 0.85 2.34 2.910(12) 125.2 2_655
O10 H101 O2 0.85 2.46 3.203(8) 145.7 2_645
O10 H102 O5 0.85 2.03 2.868(6) 166.5 1_655
O10 H102 O6 0.85 2.66 3.092(6) 112.8 1_655
O11 H112 O1 0.85 2.44 3.090(11) 134.2 2_545
O11 H112 O3 0.85 2.52 3.328(12) 158.4 2_545
O12 H121 O11 0.85 1.85 2.542(17) 137.6 .
O12 H122 O4 0.85 2.23 2.857(11) 131.0 3_575
O12 H122 O5 0.85 2.57 3.247(11) 136.9 2_545
O2 H2A O8 0.82 1.81 2.611(4) 165.9 3_676

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.988
_refine_diff_density_min         -0.961
_refine_diff_density_rms         0.113
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_6-ER
_database_code_depnum_ccdc_archive 'CCDC 1439797'
_audit_update_record             
;
2016-02-01 deposited with the CCDC.
2016-02-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_absolute_configuration ad
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H12 Er2 N O15 P, H2 O'
_chemical_formula_sum            'C10 H14 Er2 N O16 P'
_chemical_formula_weight         769.71

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Er Er -0.2586 4.9576 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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

_cell_length_a                   10.989(2)
_cell_length_b                   11.526(2)
_cell_length_c                   14.980(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1897.3(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    18502
_cell_measurement_theta_min      3.24
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.42
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.695
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1440
_exptl_absorpt_coefficient_mu    8.955
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1039
_exptl_absorpt_correction_T_max  0.1159
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            14804
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_sigmaI/netI    0.0304
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.24
_diffrn_reflns_theta_max         24.98
_reflns_number_total             3323
_reflns_number_gt                3296
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'RAPID-AUTO (Rigaku Corporation, 1998)'
_computing_cell_refinement       RAPID-AUTO
_computing_data_reduction        
'CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2002)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXL-97

_refine_special_details          
; 
OMIT  -2.00  50.00 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0000P)²+4.2413P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.009(10)
_refine_ls_number_reflns         3323
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0161
_refine_ls_R_factor_gt           0.0157
_refine_ls_wR_factor_ref         0.0397
_refine_ls_wR_factor_gt          0.0396
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2901(6) 0.9419(5) 0.7494(4) 0.0317(15) Uani 1 1 d . . .
H1 H 0.2263 0.9729 0.7825 0.038 Uiso 1 1 calc R . .
C2 C 0.3945(7) 1.0035(5) 0.7376(5) 0.0452(19) Uani 1 1 d . . .
H2 H 0.4022 1.0763 0.7638 0.054 Uiso 1 1 calc R . .
C3 C 0.4894(7) 0.9592(6) 0.6872(4) 0.0439(17) Uani 1 1 d . . .
H3 H 0.5598 1.0021 0.6776 0.053 Uiso 1 1 calc R . .
C4 C 0.4763(5) 0.8493(5) 0.6515(4) 0.0323(14) Uani 1 1 d . . .
H4 H 0.5395 0.8177 0.6181 0.039 Uiso 1 1 calc R . .
C5 C 0.3710(4) 0.7854(5) 0.6643(3) 0.0174(10) Uani 1 1 d . . .
C6 C 0.3517(4) 0.6680(4) 0.6264(3) 0.0180(10) Uani 1 1 d . . .
H6A H 0.3052 0.6221 0.6686 0.022 Uiso 1 1 calc R . .
H6B H 0.4302 0.6307 0.6187 0.022 Uiso 1 1 calc R . .
C7 C 0.3438(4) 0.6318(4) 0.2084(3) 0.0129(10) Uani 1 1 d . . .
C8 C 0.3704(4) 0.7576(4) 0.1811(3) 0.0134(10) Uani 1 1 d . . .
C9 C 0.5193(4) 0.2807(4) 0.5571(3) 0.0141(9) Uani 1 1 d . . .
C10 C 0.4707(4) 0.1764(4) 0.5013(3) 0.0123(10) Uani 1 1 d . . .
Er1 Er 0.508633(17) 0.731341(17) 0.366020(13) 0.00928(6) Uani 1 1 d . . .
Er2 Er 0.252502(19) 0.353573(15) 0.507980(12) 0.00903(6) Uani 1 1 d . . .
N1 N 0.2796(4) 0.8347(4) 0.7125(2) 0.0150(9) Uani 1 1 d . . .
O1 O 0.3508(3) 0.7406(3) 0.4562(2) 0.0162(8) Uani 1 1 d . . .
O2 O 0.2633(3) 0.5437(3) 0.4892(2) 0.0161(7) Uani 1 1 d . . .
O3 O 0.1489(3) 0.7252(3) 0.5329(2) 0.0147(7) Uani 1 1 d . . .
O4 O 0.1753(3) 0.7769(4) 0.7279(2) 0.0177(7) Uani 1 1 d . . .
O5 O 0.3953(3) 0.5960(3) 0.2789(2) 0.0204(8) Uani 1 1 d . . .
O6 O 0.2793(3) 0.5738(3) 0.1579(2) 0.0185(8) Uani 1 1 d . . .
O7 O 0.4338(4) 0.8162(3) 0.2329(2) 0.0232(8) Uani 1 1 d . . .
O8 O 0.3291(3) 0.7908(3) 0.1078(2) 0.0219(8) Uani 1 1 d . . .
O9 O 0.4463(3) 0.3612(3) 0.5703(3) 0.0245(9) Uani 1 1 d . . .
O10 O 0.6285(3) 0.2722(3) 0.5816(2) 0.0204(8) Uani 1 1 d . . .
O11 O 0.3632(3) 0.1813(3) 0.4754(2) 0.0176(7) Uani 1 1 d . . .
O12 O 0.5450(3) 0.0961(3) 0.4867(2) 0.0171(7) Uani 1 1 d . . .
O13 O 0.4867(4) 0.9319(3) 0.3702(2) 0.0256(8) Uani 1 1 d . . .
H131 H 0.5055 0.9873 0.4051 0.038 Uiso 1 1 d R . .
H132 H 0.4932 0.9780 0.3262 0.038 Uiso 1 1 d R . .
O14 O 0.5693(4) 0.5495(3) 0.4111(3) 0.0321(10) Uani 1 1 d . . .
H141 H 0.6248 0.5069 0.3931 0.048 Uiso 1 1 d R . .
H142 H 0.5324 0.5179 0.4557 0.048 Uiso 1 1 d R . .
O15 O 0.3162(4) 0.3843(3) 0.3619(3) 0.0310(10) Uani 1 1 d . . .
H151 H 0.3322 0.4466 0.3340 0.047 Uiso 1 1 d R . .
H152 H 0.3319 0.3280 0.3271 0.047 Uiso 1 1 d R . .
O16 O 0.2227(4) 0.9653(4) 0.4554(3) 0.0497(13) Uani 1 1 d . . .
H161 H 0.2484 1.0337 0.4649 0.075 Uiso 1 1 d R . .
H162 H 0.2550 0.9025 0.4733 0.075 Uiso 1 1 d R . .
P1 P 0.27216(11) 0.66828(9) 0.51917(8) 0.0093(2) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.358(7) . ?
C1 C2 1.361(10) . ?
C1 H1 0.9300 . ?
C2 C3 1.385(10) . ?
C2 H2 0.9300 . ?
C3 C4 1.382(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.385(7) . ?
C4 H4 0.9300 . ?
C5 N1 1.361(6) . ?
C5 C6 1.483(7) . ?
C6 P1 1.829(5) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 O6 1.234(6) . ?
C7 O5 1.268(6) . ?
C7 C8 1.534(7) . ?
C8 O7 1.242(6) . ?
C8 O8 1.248(6) . ?
C9 O9 1.243(6) . ?
C9 O10 1.259(6) . ?
C9 C10 1.558(6) . ?
C10 O11 1.245(6) . ?
C10 O12 1.254(5) . ?
Er1 O1 2.202(3) . ?
Er1 O3 2.218(3) 4_566 ?
Er1 O14 2.301(4) . ?
Er1 O4 2.311(3) 4_566 ?
Er1 O13 2.325(3) . ?
Er1 O7 2.368(3) . ?
Er1 O5 2.384(3) . ?
Er2 O2 2.213(3) . ?
Er2 O15 2.325(4) . ?
Er2 O9 2.327(3) . ?
Er2 O12 2.354(3) 4_456 ?
Er2 O11 2.379(3) . ?
Er2 O10 2.400(3) 4_456 ?
Er2 O8 2.410(3) 2_565 ?
Er2 O6 2.422(3) 2_565 ?
N1 O4 1.346(5) . ?
O1 P1 1.526(3) . ?
O2 P1 1.507(3) . ?
O3 P1 1.519(3) . ?
O3 Er1 2.218(3) 4_466 ?
O4 Er1 2.311(3) 4_466 ?
O6 Er2 2.422(3) 2_564 ?
O8 Er2 2.410(3) 2_564 ?
O10 Er2 2.400(3) 4_556 ?
O12 Er2 2.354(3) 4_556 ?
O13 H131 0.8501 . ?
O13 H132 0.8500 . ?
O14 H141 0.8283 . ?
O14 H142 0.8614 . ?
O15 H151 0.8499 . ?
O15 H152 0.8500 . ?
O16 H161 0.8500 . ?
O16 H162 0.8500 . ?

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
N1 C1 C2 119.6(6) . . ?
N1 C1 H1 120.2 . . ?
C2 C1 H1 120.2 . . ?
C1 C2 C3 120.9(6) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
C4 C3 C2 118.1(6) . . ?
C4 C3 H3 121.0 . . ?
C2 C3 H3 121.0 . . ?
C3 C4 C5 121.4(6) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
N1 C5 C4 117.9(5) . . ?
N1 C5 C6 118.6(4) . . ?
C4 C5 C6 123.5(5) . . ?
C5 C6 P1 113.8(3) . . ?
C5 C6 H6A 108.8 . . ?
P1 C6 H6A 108.8 . . ?
C5 C6 H6B 108.8 . . ?
P1 C6 H6B 108.8 . . ?
H6A C6 H6B 107.7 . . ?
O6 C7 O5 126.3(5) . . ?
O6 C7 C8 117.3(4) . . ?
O5 C7 C8 116.4(4) . . ?
O7 C8 O8 126.0(5) . . ?
O7 C8 C7 117.0(4) . . ?
O8 C8 C7 117.0(4) . . ?
O9 C9 O10 128.8(5) . . ?
O9 C9 C10 116.1(4) . . ?
O10 C9 C10 115.0(4) . . ?
O11 C10 O12 126.7(4) . . ?
O11 C10 C9 117.3(4) . . ?
O12 C10 C9 116.1(4) . . ?
O1 Er1 O3 96.76(13) . 4_566 ?
O1 Er1 O14 95.27(14) . . ?
O3 Er1 O14 78.70(14) 4_566 . ?
O1 Er1 O4 179.45(13) . 4_566 ?
O3 Er1 O4 82.78(12) 4_566 4_566 ?
O14 Er1 O4 84.94(15) . 4_566 ?
O1 Er1 O13 81.59(13) . . ?
O3 Er1 O13 80.15(13) 4_566 . ?
O14 Er1 O13 158.09(13) . . ?
O4 Er1 O13 98.02(14) 4_566 . ?
O1 Er1 O7 102.89(13) . . ?
O3 Er1 O7 136.30(13) 4_566 . ?
O14 Er1 O7 136.38(13) . . ?
O4 Er1 O7 77.26(13) 4_566 . ?
O13 Er1 O7 64.94(12) . . ?
O1 Er1 O5 87.46(13) . . ?
O3 Er1 O5 152.15(13) 4_566 . ?
O14 Er1 O5 73.50(13) . . ?
O4 Er1 O5 93.08(13) 4_566 . ?
O13 Er1 O5 127.67(12) . . ?
O7 Er1 O5 68.16(12) . . ?
O2 Er2 O15 73.33(12) . . ?
O2 Er2 O9 87.95(12) . . ?
O15 Er2 O9 95.53(14) . . ?
O2 Er2 O12 79.20(12) . 4_456 ?
O15 Er2 O12 106.62(14) . 4_456 ?
O9 Er2 O12 149.72(12) . 4_456 ?
O2 Er2 O11 140.62(12) . . ?
O15 Er2 O11 77.30(13) . . ?
O9 Er2 O11 69.27(12) . . ?
O12 Er2 O11 135.04(11) 4_456 . ?
O2 Er2 O10 123.89(12) . 4_456 ?
O15 Er2 O10 74.72(13) . 4_456 ?
O9 Er2 O10 140.08(12) . 4_456 ?
O12 Er2 O10 67.52(11) 4_456 4_456 ?
O11 Er2 O10 70.83(12) . 4_456 ?
O2 Er2 O8 141.51(12) . 2_565 ?
O15 Er2 O8 143.25(12) . 2_565 ?
O9 Er2 O8 96.77(13) . 2_565 ?
O12 Er2 O8 77.80(12) 4_456 2_565 ?
O11 Er2 O8 75.00(12) . 2_565 ?
O10 Er2 O8 73.67(12) 4_456 2_565 ?
O2 Er2 O6 77.49(11) . 2_565 ?
O15 Er2 O6 149.73(12) . 2_565 ?
O9 Er2 O6 75.36(12) . 2_565 ?
O12 Er2 O6 75.14(12) 4_456 2_565 ?
O11 Er2 O6 123.54(12) . 2_565 ?
O10 Er2 O6 130.19(11) 4_456 2_565 ?
O8 Er2 O6 67.02(11) 2_565 2_565 ?
O4 N1 C1 116.9(4) . . ?
O4 N1 C5 120.9(4) . . ?
C1 N1 C5 122.2(5) . . ?
P1 O1 Er1 143.0(2) . . ?
P1 O2 Er2 155.33(19) . . ?
P1 O3 Er1 144.07(19) . 4_466 ?
N1 O4 Er1 126.2(3) . 4_466 ?
C7 O5 Er1 118.5(3) . . ?
C7 O6 Er2 117.7(3) . 2_564 ?
C8 O7 Er1 119.8(3) . . ?
C8 O8 Er2 118.0(3) . 2_564 ?
C9 O9 Er2 119.9(3) . . ?
C9 O10 Er2 115.2(3) . 4_556 ?
C10 O11 Er2 117.3(3) . . ?
C10 O12 Er2 116.3(3) . 4_556 ?
Er1 O13 H131 137.6 . . ?
Er1 O13 H132 126.3 . . ?
H131 O13 H132 89.2 . . ?
Er1 O14 H141 131.1 . . ?
Er1 O14 H142 118.5 . . ?
H141 O14 H142 110.4 . . ?
Er2 O15 H151 130.8 . . ?
Er2 O15 H152 121.5 . . ?
H151 O15 H152 107.6 . . ?
H161 O16 H162 126.8 . . ?
O2 P1 O3 113.2(2) . . ?
O2 P1 O1 111.84(19) . . ?
O3 P1 O1 110.7(2) . . ?
O2 P1 C6 106.9(2) . . ?
O3 P1 C6 108.0(2) . . ?
O1 P1 C6 105.9(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O16 H161 O11 0.85 2.12 2.945(6) 162.4 1_565
O16 H162 O1 0.85 2.16 2.948(6) 154.6 .
O15 H152 O4 0.85 1.92 2.736(5) 161.6 2_564
O15 H151 O5 0.85 2.03 2.873(5) 170.9 .
O14 H142 O9 0.86 2.67 3.495(6) 162.3 .
O14 H141 O8 0.83 2.54 3.197(5) 136.8 3_645
O13 H132 O5 0.85 2.42 3.202(5) 154.2 3_655
O13 H131 O12 0.85 1.81 2.653(5) 175.2 1_565

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        24.98
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.970
_refine_diff_density_rms         0.124
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_7-Tm
_database_code_depnum_ccdc_archive 'CCDC 1439798'
_audit_update_record             
;
2016-02-01 deposited with the CCDC.
2016-02-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_absolute_configuration ad
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H12 Tm2 N O15 P, H2 O'
_chemical_formula_sum            'C10 H14 N O16 P Tm2'
_chemical_formula_weight         773.05

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'
Tm Tm -0.3139 5.2483 '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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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

_cell_length_a                   10.9138(3)
_cell_length_b                   11.4793(3)
_cell_length_c                   14.9124(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1868.27(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2878
_cell_measurement_theta_min      3.2514
_cell_measurement_theta_max      28.7128

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.748
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1448
_exptl_absorpt_coefficient_mu    9.607
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2738
_exptl_absorpt_correction_T_max  0.2936
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1954
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4528
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_sigmaI/netI    0.0427
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.26
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3035
_reflns_number_gt                2976
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
omit -2 50
isor 0.01 n1 c3 c7
delu 0.02 o5 c7
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0510P)²+5.6033P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(2)
_refine_ls_number_reflns         3035
_refine_ls_number_parameters     271
_refine_ls_number_restraints     19
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0330
_refine_ls_wR_factor_ref         0.0839
_refine_ls_wR_factor_gt          0.0832
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.047
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7093(12) 0.0558(10) 0.2503(8) 0.028(3) Uani 1 1 d . . .
H1 H 0.7730 0.0249 0.2164 0.033 Uiso 1 1 calc R . .
C2 C 0.6082(15) -0.0045(11) 0.2620(9) 0.037(4) Uani 1 1 d . . .
H2 H 0.6014 -0.0782 0.2366 0.044 Uiso 1 1 calc R . .
C3 C 0.5112(14) 0.0398(11) 0.3119(8) 0.039(3) Uani 1 1 d U . .
H3 H 0.4402 -0.0037 0.3204 0.047 Uiso 1 1 calc R . .
C4 C 0.5228(11) 0.1503(11) 0.3486(7) 0.029(3) Uani 1 1 d . . .
H4 H 0.4593 0.1810 0.3828 0.035 Uiso 1 1 calc R . .
C5 C 0.6285(9) 0.2154(10) 0.3347(6) 0.015(2) Uani 1 1 d . . .
C6 C 0.6481(9) 0.3319(10) 0.3728(7) 0.018(2) Uani 1 1 d . . .
H6A H 0.5692 0.3695 0.3803 0.022 Uiso 1 1 calc R . .
H6B H 0.6951 0.3779 0.3304 0.022 Uiso 1 1 calc R . .
C7 C 0.6544(10) 0.3698(10) 0.7921(7) 0.016(2) Uani 1 1 d U . .
C8 C 0.6298(10) 0.2423(9) 0.8196(6) 0.016(2) Uani 1 1 d . . .
C9 C 0.4803(10) 0.7194(9) 0.4428(6) 0.013(2) Uani 1 1 d . . .
C10 C 0.5296(8) 0.8236(8) 0.4984(6) 0.010(2) Uani 1 1 d . . .
Tm1 Tm 0.49138(4) 0.26876(4) 0.63393(3) 0.00839(13) Uani 1 1 d . . .
Tm2 Tm 0.74782(4) 0.64671(3) 0.49197(2) 0.00830(13) Uani 1 1 d . . .
N1 N 0.7209(8) 0.1650(8) 0.2881(5) 0.0157(19) Uani 1 1 d U . .
O1 O 0.6497(7) 0.2612(7) 0.5440(5) 0.0167(17) Uani 1 1 d . . .
O2 O 0.7369(6) 0.4569(5) 0.5104(4) 0.0140(14) Uani 1 1 d . . .
O3 O 0.8513(6) 0.2735(7) 0.4673(4) 0.0131(15) Uani 1 1 d . . .
O4 O 0.8252(6) 0.2225(7) 0.2723(4) 0.0163(16) Uani 1 1 d . . .
O5 O 0.6042(7) 0.4048(6) 0.7213(5) 0.0184(17) Uani 1 1 d U . .
O6 O 0.7203(7) 0.4268(6) 0.8426(4) 0.0179(17) Uani 1 1 d . . .
O7 O 0.5655(7) 0.1840(6) 0.7665(5) 0.0210(18) Uani 1 1 d . . .
O8 O 0.6712(7) 0.2089(6) 0.8920(4) 0.0190(17) Uani 1 1 d . . .
O9 O 0.5552(6) 0.6378(7) 0.4294(5) 0.0223(18) Uani 1 1 d . . .
O10 O 0.3703(6) 0.7275(7) 0.4181(5) 0.0176(16) Uani 1 1 d . . .
O11 O 0.6374(6) 0.8185(6) 0.5246(5) 0.0162(16) Uani 1 1 d . . .
O12 O 0.4549(6) 0.9039(6) 0.5133(5) 0.0159(16) Uani 1 1 d . . .
O13 O 0.5124(7) 0.0688(6) 0.6293(5) 0.0247(18) Uani 1 1 d . . .
H131 H 0.4935 0.0130 0.5942 0.037 Uiso 1 1 d R . .
H132 H 0.5059 0.0223 0.6737 0.037 Uiso 1 1 d R . .
O14 O 0.4307(8) 0.4494(7) 0.5876(5) 0.028(2) Uani 1 1 d . . .
H141 H 0.3738 0.4943 0.6064 0.042 Uiso 1 1 d R . .
H142 H 0.4662 0.4833 0.5438 0.042 Uiso 1 1 d R . .
O15 O 0.6842(7) 0.6152(6) 0.6367(5) 0.0268(19) Uani 1 1 d . . .
H151 H 0.6680 0.5523 0.6648 0.040 Uiso 1 1 d R . .
H152 H 0.6684 0.6719 0.6718 0.040 Uiso 1 1 d R . .
O16 O 0.7781(9) 0.0354(8) 0.5461(6) 0.043(3) Uani 1 1 d . . .
H161 H 0.7522 -0.0336 0.5366 0.065 Uiso 1 1 d R . .
H162 H 0.7455 0.0987 0.5281 0.065 Uiso 1 1 d R . .
P1 P 0.7282(2) 0.3323(2) 0.48105(16) 0.0082(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
C1 C2 1.315(19) . ?
C1 N1 1.380(14) . ?
C1 H1 0.9300 . ?
C2 C3 1.39(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.388(16) . ?
C3 H3 0.9300 . ?
C4 C5 1.390(15) . ?
C4 H4 0.9300 . ?
C5 N1 1.355(13) . ?
C5 C6 1.468(15) . ?
C6 P1 1.836(11) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 O6 1.229(12) . ?
C7 O5 1.257(12) . ?
C7 C8 1.543(15) . ?
C8 O8 1.232(12) . ?
C8 O7 1.252(12) . ?
C9 O10 1.259(12) . ?
C9 O9 1.259(12) . ?
C9 C10 1.551(13) . ?
C10 O11 1.241(11) . ?
C10 O12 1.251(11) . ?
Tm1 O1 2.189(7) . ?
Tm1 O3 2.203(7) 4_456 ?
Tm1 O14 2.284(8) . ?
Tm1 O4 2.292(7) 4_456 ?
Tm1 O13 2.308(7) . ?
Tm1 O7 2.347(7) . ?
Tm1 O5 2.377(7) . ?
Tm2 O2 2.200(6) . ?
Tm2 O15 2.296(7) . ?
Tm2 O9 2.302(7) . ?
Tm2 O12 2.335(6) 4_566 ?
Tm2 O11 2.362(7) . ?
Tm2 O10 2.382(7) 4_566 ?
Tm2 O8 2.399(7) 2_664 ?
Tm2 O6 2.407(7) 2_664 ?
N1 O4 1.337(11) . ?
O1 P1 1.510(8) . ?
O2 P1 1.499(7) . ?
O3 P1 1.516(7) . ?
O3 Tm1 2.203(7) 4_556 ?
O4 Tm1 2.292(7) 4_556 ?
O6 Tm2 2.407(7) 2_665 ?
O8 Tm2 2.399(7) 2_665 ?
O10 Tm2 2.382(7) 4_466 ?
O12 Tm2 2.335(6) 4_466 ?
O13 H131 0.8531 . ?
O13 H132 0.8532 . ?
O14 H141 0.8540 . ?
O14 H142 0.8537 . ?
O15 H151 0.8529 . ?
O15 H152 0.8531 . ?
O16 H161 0.8528 . ?
O16 H162 0.8530 . ?

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
C2 C1 N1 120.0(12) . . ?
C2 C1 H1 120.0 . . ?
N1 C1 H1 120.0 . . ?
C1 C2 C3 121.2(12) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 H2 119.4 . . ?
C4 C3 C2 118.4(13) . . ?
C4 C3 H3 120.8 . . ?
C2 C3 H3 120.8 . . ?
C3 C4 C5 120.6(12) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
N1 C5 C4 117.6(11) . . ?
N1 C5 C6 118.6(9) . . ?
C4 C5 C6 123.6(10) . . ?
C5 C6 P1 114.3(7) . . ?
C5 C6 H6A 108.7 . . ?
P1 C6 H6A 108.7 . . ?
C5 C6 H6B 108.7 . . ?
P1 C6 H6B 108.7 . . ?
H6A C6 H6B 107.6 . . ?
O6 C7 O5 126.9(10) . . ?
O6 C7 C8 116.4(9) . . ?
O5 C7 C8 116.8(9) . . ?
O8 C8 O7 126.4(10) . . ?
O8 C8 C7 117.6(10) . . ?
O7 C8 C7 115.9(9) . . ?
O10 C9 O9 128.9(10) . . ?
O10 C9 C10 115.5(9) . . ?
O9 C9 C10 115.7(9) . . ?
O11 C10 O12 126.6(9) . . ?
O11 C10 C9 117.4(8) . . ?
O12 C10 C9 116.0(8) . . ?
O1 Tm1 O3 96.9(3) . 4_456 ?
O1 Tm1 O14 94.6(3) . . ?
O3 Tm1 O14 78.0(3) 4_456 . ?
O1 Tm1 O4 179.7(3) . 4_456 ?
O3 Tm1 O4 83.0(2) 4_456 4_456 ?
O14 Tm1 O4 85.1(3) . 4_456 ?
O1 Tm1 O13 82.2(3) . . ?
O3 Tm1 O13 80.2(3) 4_456 . ?
O14 Tm1 O13 157.3(3) . . ?
O4 Tm1 O13 98.1(3) 4_456 . ?
O1 Tm1 O7 103.2(3) . . ?
O3 Tm1 O7 136.5(3) 4_456 . ?
O14 Tm1 O7 137.0(3) . . ?
O4 Tm1 O7 77.1(3) 4_456 . ?
O13 Tm1 O7 65.1(2) . . ?
O1 Tm1 O5 87.3(3) . . ?
O3 Tm1 O5 151.6(3) 4_456 . ?
O14 Tm1 O5 73.7(3) . . ?
O4 Tm1 O5 92.7(3) 4_456 . ?
O13 Tm1 O5 128.2(3) . . ?
O7 Tm1 O5 68.4(2) . . ?
O2 Tm2 O15 73.1(2) . . ?
O2 Tm2 O9 87.5(3) . . ?
O15 Tm2 O9 95.6(3) . . ?
O2 Tm2 O12 79.1(2) . 4_566 ?
O15 Tm2 O12 106.6(3) . 4_566 ?
O9 Tm2 O12 149.2(3) . 4_566 ?
O2 Tm2 O11 140.7(3) . . ?
O15 Tm2 O11 77.5(3) . . ?
O9 Tm2 O11 69.8(2) . . ?
O12 Tm2 O11 135.1(2) 4_566 . ?
O2 Tm2 O10 124.1(3) . 4_566 ?
O15 Tm2 O10 74.7(3) . 4_566 ?
O9 Tm2 O10 140.2(3) . 4_566 ?
O12 Tm2 O10 68.1(2) 4_566 4_566 ?
O11 Tm2 O10 70.4(2) . 4_566 ?
O2 Tm2 O8 141.5(2) . 2_664 ?
O15 Tm2 O8 143.6(2) . 2_664 ?
O9 Tm2 O8 96.6(3) . 2_664 ?
O12 Tm2 O8 78.1(3) 4_566 2_664 ?
O11 Tm2 O8 74.9(3) . 2_664 ?
O10 Tm2 O8 74.0(2) 4_566 2_664 ?
O2 Tm2 O6 77.1(2) . 2_664 ?
O15 Tm2 O6 149.1(3) . 2_664 ?
O9 Tm2 O6 75.0(3) . 2_664 ?
O12 Tm2 O6 75.0(3) 4_566 2_664 ?
O11 Tm2 O6 123.8(3) . 2_664 ?
O10 Tm2 O6 130.7(2) 4_566 2_664 ?
O8 Tm2 O6 67.3(2) 2_664 2_664 ?
O4 N1 C5 120.9(9) . . ?
O4 N1 C1 117.0(9) . . ?
C5 N1 C1 122.0(10) . . ?
P1 O1 Tm1 143.8(5) . . ?
P1 O2 Tm2 155.8(4) . . ?
P1 O3 Tm1 143.6(4) . 4_556 ?
N1 O4 Tm1 126.0(6) . 4_556 ?
C7 O5 Tm1 118.5(7) . . ?
C7 O6 Tm2 117.7(7) . 2_665 ?
C8 O7 Tm1 120.3(7) . . ?
C8 O8 Tm2 117.7(7) . 2_665 ?
C9 O9 Tm2 119.7(7) . . ?
C9 O10 Tm2 114.5(6) . 4_466 ?
C10 O11 Tm2 117.3(6) . . ?
C10 O12 Tm2 116.2(6) . 4_466 ?
Tm1 O13 H131 137.9 . . ?
Tm1 O13 H132 126.2 . . ?
H131 O13 H132 89.2 . . ?
Tm1 O14 H141 131.2 . . ?
Tm1 O14 H142 120.9 . . ?
H141 O14 H142 107.8 . . ?
Tm2 O15 H151 131.1 . . ?
Tm2 O15 H152 121.2 . . ?
H151 O15 H152 107.6 . . ?
H161 O16 H162 126.9 . . ?
O2 P1 O1 111.7(4) . . ?
O2 P1 O3 114.1(4) . . ?
O1 P1 O3 110.2(5) . . ?
O2 P1 C6 106.8(4) . . ?
O1 P1 C6 106.0(5) . . ?
O3 P1 C6 107.6(4) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O13 H131 O12 0.85 1.79 2.640(10) 175.4 1_545
O13 H132 O5 0.85 2.39 3.183(11) 154.6 3_646
O14 H141 O8 0.85 2.51 3.194(11) 137.5 3_656
O14 H142 O9 0.85 2.65 3.477(12) 165.0 .
O15 H151 O5 0.85 2.02 2.861(10) 171.0 .
O15 H152 O4 0.85 1.93 2.752(11) 161.7 2_665
O16 H162 O3 0.85 2.49 3.081(12) 127.6 .
O16 H161 O11 0.85 2.12 2.942(12) 162.7 1_545

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         1.017
_refine_diff_density_min         -2.204
_refine_diff_density_rms         0.279
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_8-YB
_database_code_depnum_ccdc_archive 'CCDC 1439799'
_audit_update_record             
;
2016-02-01 deposited with the CCDC.
2016-02-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_absolute_configuration ad
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H12 Yb2 N O15 P, H2 O'
_chemical_formula_sum            'C10 H14 N O16 P Yb2'
_chemical_formula_weight         781.27

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'
Yb Yb -0.3850 5.5486 '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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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

_cell_length_a                   10.901(2)
_cell_length_b                   11.447(2)
_cell_length_c                   14.890(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1858.0(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    17216
_cell_measurement_theta_min      3.27
_cell_measurement_theta_max      27.65

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.793
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1456
_exptl_absorpt_coefficient_mu    10.177
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.1993
_exptl_absorpt_correction_T_max  0.2193
_exptl_absorpt_process_details   
;
'ABSCOR (Higashi, 1995)' 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            13881
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_sigmaI/netI    0.0346
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.26
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3231
_reflns_number_gt                3170
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'RAPID-AUTO (Rigaku Corporation, 1998)'
_computing_cell_refinement       RAPID-AUTO
_computing_data_reduction        
'CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2002)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
FREE C10  Yb2
FREE C9   Yb2
FREE Yb1  P1
FREE C8   Yb1
FREE C7   Yb1
omit     3  10   3
omit    11   1   1
omit     0  11   4
omit    -4   2   2
omit     2   0   1
omit     3  12   4
OMIT  -2.00  50.00
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0201P)²+0.3323P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.009(10)
_refine_ls_number_reflns         3231
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0247
_refine_ls_R_factor_gt           0.0234
_refine_ls_wR_factor_ref         0.0466
_refine_ls_wR_factor_gt          0.0463
_refine_ls_goodness_of_fit_ref   1.147
_refine_ls_restrained_S_all      1.147
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2897(6) 0.9420(8) 0.7476(5) 0.0369(19) Uani 1 1 d . . .
H1 H 0.2248 0.9740 0.7798 0.044 Uiso 1 1 calc R . .
C2 C 0.3952(8) 1.0043(7) 0.7367(5) 0.047(2) Uani 1 1 d . . .
H2 H 0.4028 1.0774 0.7635 0.056 Uiso 1 1 calc R . .
C3 C 0.4895(6) 0.9610(7) 0.6871(5) 0.045(2) Uani 1 1 d . . .
H3 H 0.5603 1.0043 0.6769 0.054 Uiso 1 1 calc R . .
C4 C 0.4757(5) 0.8501(7) 0.6525(4) 0.0347(17) Uani 1 1 d . . .
H4 H 0.5401 0.8179 0.6198 0.042 Uiso 1 1 calc R . .
C5 C 0.3718(5) 0.7852(6) 0.6641(4) 0.0204(14) Uani 1 1 d . . .
C6 C 0.3539(5) 0.6674(6) 0.6271(4) 0.0207(14) Uani 1 1 d . . .
H6A H 0.3081 0.6209 0.6701 0.025 Uiso 1 1 calc R . .
H6B H 0.4334 0.6308 0.6190 0.025 Uiso 1 1 calc R . .
C7 C 0.3447(5) 0.6323(6) 0.2090(4) 0.0157(13) Uani 1 1 d . . .
C8 C 0.3706(4) 0.7572(5) 0.1812(3) 0.0152(13) Uani 1 1 d . . .
C9 C 0.5192(5) 0.2822(6) 0.5563(4) 0.0154(11) Uani 1 1 d . . .
C10 C 0.4706(5) 0.1773(5) 0.5016(4) 0.0151(12) Uani 1 1 d . . .
Yb1 Yb 0.508591(18) 0.73139(2) 0.366094(15) 0.01202(7) Uani 1 1 d . . .
Yb2 Yb 0.251893(18) 0.35305(2) 0.508224(13) 0.01164(7) Uani 1 1 d . . .
N1 N 0.2790(4) 0.8358(5) 0.7125(3) 0.0162(11) Uani 1 1 d . . .
O1 O 0.3512(3) 0.7392(4) 0.4552(3) 0.0172(10) Uani 1 1 d . . .
O2 O 0.2634(3) 0.5423(4) 0.4901(2) 0.0173(8) Uani 1 1 d . . .
O3 O 0.1489(3) 0.7255(4) 0.5335(2) 0.0172(9) Uani 1 1 d . . .
O4 O 0.1736(3) 0.7763(5) 0.7272(3) 0.0198(9) Uani 1 1 d . . .
O5 O 0.3957(4) 0.5965(4) 0.2802(3) 0.0220(10) Uani 1 1 d . . .
O6 O 0.2795(3) 0.5733(4) 0.1573(3) 0.0197(10) Uani 1 1 d . . .
O7 O 0.4342(4) 0.8171(4) 0.2335(3) 0.0253(11) Uani 1 1 d . . .
O8 O 0.3283(4) 0.7908(4) 0.1074(3) 0.0254(10) Uani 1 1 d . . .
O9 O 0.4451(3) 0.3628(4) 0.5702(3) 0.0257(11) Uani 1 1 d . . .
O10 O 0.6296(3) 0.2734(4) 0.5815(3) 0.0215(9) Uani 1 1 d . . .
O11 O 0.3620(3) 0.1821(4) 0.4760(3) 0.0201(10) Uani 1 1 d . . .
O12 O 0.5452(3) 0.0968(4) 0.4865(3) 0.0202(9) Uani 1 1 d . . .
O13 O 0.4865(4) 0.9305(4) 0.3717(3) 0.0279(10) Uani 1 1 d . . .
H131 H 0.5055 0.9863 0.4069 0.042 Uiso 1 1 d R . .
H132 H 0.4930 0.9770 0.3274 0.042 Uiso 1 1 d R . .
O14 O 0.5683(4) 0.5509(4) 0.4111(3) 0.0324(12) Uani 1 1 d . . .
H141 H 0.6252 0.5060 0.3923 0.049 Uiso 1 1 d R . .
H142 H 0.5328 0.5170 0.4549 0.049 Uiso 1 1 d R . .
O15 O 0.3163(4) 0.3841(4) 0.3639(3) 0.0317(11) Uani 1 1 d . . .
H151 H 0.3325 0.4469 0.3358 0.048 Uiso 1 1 d R . .
H152 H 0.3321 0.3274 0.3288 0.048 Uiso 1 1 d R . .
O16 O 0.2222(4) 0.9639(5) 0.4535(4) 0.0516(15) Uani 1 1 d . . .
H161 H 0.2480 1.0329 0.4631 0.077 Uiso 1 1 d R . .
H162 H 0.2548 0.9006 0.4716 0.077 Uiso 1 1 d R . .
P1 P 0.27181(11) 0.66679(13) 0.51919(9) 0.0119(3) 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
C1 N1 1.328(9) . ?
C1 C2 1.363(11) . ?
C1 H1 0.9300 . ?
C2 C3 1.360(11) . ?
C2 H2 0.9300 . ?
C3 C4 1.378(11) . ?
C3 H3 0.9300 . ?
C4 C5 1.365(8) . ?
C4 H4 0.9300 . ?
C5 N1 1.371(7) . ?
C5 C6 1.470(9) . ?
C6 P1 1.839(6) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 O6 1.248(7) . ?
C7 O5 1.265(7) . ?
C7 C8 1.514(9) . ?
C7 Yb2 3.174(5) 2_564 ?
C8 O7 1.249(7) . ?
C8 O8 1.253(6) . ?
C8 Yb2 3.163(5) 2_564 ?
C9 O9 1.244(7) . ?
C9 O10 1.265(6) . ?
C9 C10 1.544(8) . ?
C9 Yb2 3.123(5) 4_556 ?
C10 O11 1.245(6) . ?
C10 O12 1.249(6) . ?
C10 Yb2 3.089(5) 4_556 ?
Yb1 O1 2.171(3) . ?
Yb1 O3 2.195(4) 4_566 ?
Yb1 O14 2.267(5) . ?
Yb1 O4 2.274(4) 4_566 ?
Yb1 O13 2.293(4) . ?
Yb1 O7 2.349(4) . ?
Yb1 O5 2.352(4) . ?
Yb1 P1 3.5368(14) 4_566 ?
Yb2 O2 2.187(4) . ?
Yb2 O15 2.288(4) . ?
Yb2 O9 2.302(4) . ?
Yb2 O12 2.327(3) 4_456 ?
Yb2 O11 2.345(4) . ?
Yb2 O8 2.378(4) 2_565 ?
Yb2 O10 2.379(4) 4_456 ?
Yb2 O6 2.399(4) 2_565 ?
Yb2 C10 3.089(5) 4_456 ?
Yb2 C9 3.123(5) 4_456 ?
Yb2 C8 3.163(5) 2_565 ?
Yb2 C7 3.174(5) 2_565 ?
N1 O4 1.354(6) . ?
O1 P1 1.531(4) . ?
O2 P1 1.492(4) . ?
O3 P1 1.514(4) . ?
O3 Yb1 2.195(4) 4_466 ?
O4 Yb1 2.274(4) 4_466 ?
O6 Yb2 2.399(4) 2_564 ?
O8 Yb2 2.378(4) 2_564 ?
O10 Yb2 2.379(4) 4_556 ?
O12 Yb2 2.327(3) 4_556 ?
O13 H131 0.8512 . ?
O13 H132 0.8515 . ?
O14 H141 0.8524 . ?
O14 H142 0.8523 . ?
O15 H151 0.8508 . ?
O15 H152 0.8512 . ?
O16 H161 0.8506 . ?
O16 H162 0.8509 . ?
P1 Yb1 3.5368(13) 4_466 ?

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
N1 C1 C2 120.4(7) . . ?
N1 C1 H1 119.8 . . ?
C2 C1 H1 119.8 . . ?
C3 C2 C1 120.8(7) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 117.2(6) . . ?
C2 C3 H3 121.4 . . ?
C4 C3 H3 121.4 . . ?
C5 C4 C3 123.0(7) . . ?
C5 C4 H4 118.5 . . ?
C3 C4 H4 118.5 . . ?
C4 C5 N1 116.7(6) . . ?
C4 C5 C6 124.2(6) . . ?
N1 C5 C6 119.1(5) . . ?
C5 C6 P1 113.3(4) . . ?
C5 C6 H6A 108.9 . . ?
P1 C6 H6A 108.9 . . ?
C5 C6 H6B 108.9 . . ?
P1 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
O6 C7 O5 126.3(6) . . ?
O6 C7 C8 116.7(5) . . ?
O5 C7 C8 116.9(5) . . ?
O5 C7 Yb2 162.2(4) . 2_564 ?
C8 C7 Yb2 75.8(3) . 2_564 ?
O7 C8 O8 125.7(6) . . ?
O7 C8 C7 116.8(5) . . ?
O8 C8 C7 117.5(5) . . ?
O7 C8 Yb2 164.1(4) . 2_564 ?
C7 C8 Yb2 76.6(3) . 2_564 ?
O9 C9 O10 128.9(6) . . ?
O9 C9 C10 116.2(5) . . ?
O10 C9 C10 114.9(5) . . ?
O9 C9 Yb2 161.2(4) . 4_556 ?
C10 C9 Yb2 74.4(3) . 4_556 ?
O11 C10 O12 126.6(5) . . ?
O11 C10 C9 116.9(5) . . ?
O12 C10 C9 116.5(5) . . ?
O11 C10 Yb2 159.1(4) . 4_556 ?
C9 C10 Yb2 76.8(3) . 4_556 ?
O1 Yb1 O3 97.18(15) . 4_566 ?
O1 Yb1 O14 94.80(17) . . ?
O3 Yb1 O14 78.69(17) 4_566 . ?
O1 Yb1 O4 179.86(19) . 4_566 ?
O3 Yb1 O4 82.74(13) 4_566 4_566 ?
O14 Yb1 O4 85.29(17) . 4_566 ?
O1 Yb1 O13 81.60(16) . . ?
O3 Yb1 O13 79.90(16) 4_566 . ?
O14 Yb1 O13 157.66(15) . . ?
O4 Yb1 O13 98.28(17) 4_566 . ?
O1 Yb1 O7 102.93(15) . . ?
O3 Yb1 O7 135.97(16) 4_566 . ?
O14 Yb1 O7 136.72(17) . . ?
O4 Yb1 O7 77.06(14) 4_566 . ?
O13 Yb1 O7 65.12(15) . . ?
O1 Yb1 O5 86.91(15) . . ?
O3 Yb1 O5 151.95(16) 4_566 . ?
O14 Yb1 O5 73.31(15) . . ?
O4 Yb1 O5 93.21(15) 4_566 . ?
O13 Yb1 O5 128.11(14) . . ?
O7 Yb1 O5 68.69(15) . . ?
O1 Yb1 P1 109.41(11) . 4_566 ?
O3 Yb1 P1 14.46(11) 4_566 4_566 ?
O14 Yb1 P1 85.68(11) . 4_566 ?
O4 Yb1 P1 70.49(10) 4_566 4_566 ?
O13 Yb1 P1 74.93(10) . 4_566 ?
O7 Yb1 P1 123.25(11) . 4_566 ?
O5 Yb1 P1 154.58(11) . 4_566 ?
O2 Yb2 O15 73.30(15) . . ?
O2 Yb2 O9 87.09(15) . . ?
O15 Yb2 O9 95.05(16) . . ?
O2 Yb2 O12 79.35(14) . 4_456 ?
O15 Yb2 O12 106.90(16) . 4_456 ?
O9 Yb2 O12 149.39(16) . 4_456 ?
O2 Yb2 O11 140.53(14) . . ?
O15 Yb2 O11 77.31(16) . . ?
O9 Yb2 O11 69.76(14) . . ?
O12 Yb2 O11 135.11(14) 4_456 . ?
O2 Yb2 O8 141.61(14) . 2_565 ?
O15 Yb2 O8 143.44(16) . 2_565 ?
O9 Yb2 O8 96.95(16) . 2_565 ?
O12 Yb2 O8 78.11(15) 4_456 2_565 ?
O11 Yb2 O8 74.77(15) . 2_565 ?
O2 Yb2 O10 124.43(14) . 4_456 ?
O15 Yb2 O10 74.87(15) . 4_456 ?
O9 Yb2 O10 140.12(15) . 4_456 ?
O12 Yb2 O10 68.05(14) 4_456 4_456 ?
O11 Yb2 O10 70.38(13) . 4_456 ?
O8 Yb2 O10 73.83(15) 2_565 4_456 ?
O2 Yb2 O6 76.95(14) . 2_565 ?
O15 Yb2 O6 149.08(16) . 2_565 ?
O9 Yb2 O6 75.09(14) . 2_565 ?
O12 Yb2 O6 75.17(13) 4_456 2_565 ?
O11 Yb2 O6 123.75(15) . 2_565 ?
O8 Yb2 O6 67.47(15) 2_565 2_565 ?
O10 Yb2 O6 130.84(12) 4_456 2_565 ?
O2 Yb2 C10 99.35(14) . 4_456 ?
O15 Yb2 C10 106.12(15) . 4_456 ?
O9 Yb2 C10 158.83(15) . 4_456 ?
O12 Yb2 C10 21.27(15) 4_456 4_456 ?
O11 Yb2 C10 113.86(14) . 4_456 ?
O8 Yb2 C10 65.59(15) 2_565 4_456 ?
O10 Yb2 C10 49.36(13) 4_456 4_456 ?
O6 Yb2 C10 86.67(13) 2_565 4_456 ?
O2 Yb2 C9 119.97(14) . 4_456 ?
O15 Yb2 C9 92.14(15) . 4_456 ?
O9 Yb2 C9 152.92(17) . 4_456 ?
O12 Yb2 C9 49.16(15) 4_456 4_456 ?
O11 Yb2 C9 86.52(14) . 4_456 ?
O8 Yb2 C9 63.21(15) 2_565 4_456 ?
O10 Yb2 C9 21.62(14) 4_456 4_456 ?
O6 Yb2 C9 110.07(13) 2_565 4_456 ?
C10 Yb2 C9 28.78(15) 4_456 4_456 ?
O2 Yb2 C8 121.33(14) . 2_565 ?
O15 Yb2 C8 162.92(16) . 2_565 ?
O9 Yb2 C8 94.54(15) . 2_565 ?
O12 Yb2 C8 70.26(14) 4_456 2_565 ?
O11 Yb2 C8 92.85(15) . 2_565 ?
O8 Yb2 C8 20.49(16) 2_565 2_565 ?
O10 Yb2 C8 88.75(14) 4_456 2_565 ?
O6 Yb2 C8 47.69(15) 2_565 2_565 ?
C10 Yb2 C8 64.84(13) 4_456 2_565 ?
C9 Yb2 C8 73.14(14) 4_456 2_565 ?
O2 Yb2 C7 94.77(15) . 2_565 ?
O15 Yb2 C7 167.98(17) . 2_565 ?
O9 Yb2 C7 85.62(14) . 2_565 ?
O12 Yb2 C7 68.52(14) 4_456 2_565 ?
O11 Yb2 C7 113.98(16) . 2_565 ?
O8 Yb2 C7 47.92(16) 2_565 2_565 ?
O10 Yb2 C7 112.04(14) 4_456 2_565 ?
O6 Yb2 C7 20.40(15) 2_565 2_565 ?
C10 Yb2 C7 73.81(14) 4_456 2_565 ?
C9 Yb2 C7 92.66(14) 4_456 2_565 ?
C8 Yb2 C7 27.65(16) 2_565 2_565 ?
C1 N1 O4 118.1(5) . . ?
C1 N1 C5 122.0(5) . . ?
O4 N1 C5 119.9(5) . . ?
P1 O1 Yb1 143.6(3) . . ?
P1 O2 Yb2 156.0(2) . . ?
P1 O3 Yb1 144.3(2) . 4_466 ?
N1 O4 Yb1 126.3(3) . 4_466 ?
C7 O5 Yb1 118.2(4) . . ?
C7 O6 Yb2 117.5(4) . 2_564 ?
C8 O7 Yb1 119.1(4) . . ?
C8 O8 Yb2 117.9(4) . 2_564 ?
C9 O9 Yb2 119.5(4) . . ?
C9 O10 Yb2 114.5(3) . 4_556 ?
C10 O11 Yb2 117.4(4) . . ?
C10 O12 Yb2 116.2(4) . 4_556 ?
Yb1 O13 H131 138.0 . . ?
Yb1 O13 H132 125.7 . . ?
H131 O13 H132 89.3 . . ?
Yb1 O14 H141 131.4 . . ?
Yb1 O14 H142 120.7 . . ?
H141 O14 H142 107.9 . . ?
Yb2 O15 H151 131.0 . . ?
Yb2 O15 H152 121.3 . . ?
H151 O15 H152 107.5 . . ?
H161 O16 H162 126.8 . . ?
O2 P1 O3 114.2(2) . . ?
O2 P1 O1 111.8(2) . . ?
O3 P1 O1 110.4(3) . . ?
O2 P1 C6 106.7(3) . . ?
O3 P1 C6 107.8(2) . . ?
O1 P1 C6 105.5(3) . . ?
O2 P1 Yb1 113.90(15) . 4_466 ?
O1 P1 Yb1 125.52(18) . 4_466 ?
C6 P1 Yb1 88.37(18) . 4_466 ?

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
O16 H161 O11 0.85 2.12 2.945(7) 163.2 1_565
O16 H162 O3 0.85 2.49 3.083(7) 127.5 .
O15 H152 O4 0.85 1.92 2.744(6) 161.3 2_564
O15 H151 O5 0.85 2.02 2.867(6) 171.0 .
O14 H142 O9 0.85 2.64 3.472(7) 165.1 .
O14 H141 O8 0.85 2.52 3.196(7) 137.4 3_645
O13 H132 O5 0.85 2.43 3.222(6) 154.8 3_655
O13 H131 O12 0.85 1.79 2.637(6) 176.3 1_565

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         2.535
_refine_diff_density_min         -0.742
_refine_diff_density_rms         0.186
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_9-lu
_database_code_depnum_ccdc_archive 'CCDC 1439800'
_audit_update_record             
;
2016-02-01 deposited with the CCDC.
2016-02-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_absolute_configuration ad
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H12 Lu2 N O15 P, H2 O'
_chemical_formula_sum            'C10 H14 Lu2 N O16 P'
_chemical_formula_weight         785.13

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Lu Lu -0.4720 5.8584 '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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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

_cell_length_a                   10.8491(2)
_cell_length_b                   11.4465(2)
_cell_length_c                   14.8471(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1843.78(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2735
_cell_measurement_theta_min      3.2642
_cell_measurement_theta_max      28.9665

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.828
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1464
_exptl_absorpt_coefficient_mu    10.820
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2621
_exptl_absorpt_correction_T_max  0.2848
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1954
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4641
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_sigmaI/netI    0.0465
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.27
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2949
_reflns_number_gt                2834
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
omit     2   0   4
omit     6   1  12
OMIT  -2.00  50.00
isor 0.01 o5 c5
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0147P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.014(13)
_refine_ls_number_reflns         2949
_refine_ls_number_parameters     271
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0276
_refine_ls_R_factor_gt           0.0257
_refine_ls_wR_factor_ref         0.0535
_refine_ls_wR_factor_gt          0.0527
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.062
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2889(9) 0.9429(9) 0.7484(6) 0.030(3) Uani 1 1 d . . .
H1 H 0.2247 0.9737 0.7824 0.036 Uiso 1 1 calc R . .
C2 C 0.3919(12) 1.0053(9) 0.7356(7) 0.046(3) Uani 1 1 d . . .
H2 H 0.3977 1.0799 0.7602 0.056 Uiso 1 1 calc R . .
C3 C 0.4899(11) 0.9612(9) 0.6867(6) 0.043(3) Uani 1 1 d . . .
H3 H 0.5616 1.0043 0.6779 0.051 Uiso 1 1 calc R . .
C4 C 0.4763(9) 0.8499(9) 0.6513(5) 0.031(2) Uani 1 1 d . . .
H4 H 0.5403 0.8185 0.6174 0.037 Uiso 1 1 calc R . .
C5 C 0.3716(7) 0.7843(8) 0.6644(5) 0.0169(19) Uani 1 1 d U . .
C6 C 0.3522(7) 0.6678(7) 0.6277(5) 0.0146(18) Uani 1 1 d . . .
H6A H 0.3049 0.6223 0.6707 0.018 Uiso 1 1 calc R . .
H6B H 0.4315 0.6300 0.6204 0.018 Uiso 1 1 calc R . .
C7 C 0.3446(8) 0.6320(7) 0.2091(5) 0.0126(19) Uani 1 1 d . . .
C8 C 0.3721(8) 0.7582(7) 0.1810(5) 0.014(2) Uani 1 1 d . . .
C9 C 0.5202(8) 0.2825(7) 0.5565(5) 0.0149(18) Uani 1 1 d . . .
C10 C 0.4701(8) 0.1754(6) 0.5018(5) 0.0152(19) Uani 1 1 d . . .
Lu1 Lu 0.50824(3) 0.73177(3) 0.36603(2) 0.00985(9) Uani 1 1 d . . .
Lu2 Lu 0.25147(3) 0.35279(3) 0.508284(18) 0.00962(9) Uani 1 1 d . . .
N1 N 0.2784(6) 0.8353(6) 0.7119(4) 0.0147(16) Uani 1 1 d . . .
O1 O 0.3497(5) 0.7384(5) 0.4537(3) 0.0175(14) Uani 1 1 d . . .
O2 O 0.2616(5) 0.5413(4) 0.4898(3) 0.0161(12) Uani 1 1 d . . .
O3 O 0.1477(5) 0.7251(5) 0.5331(3) 0.0150(13) Uani 1 1 d . . .
O4 O 0.1729(5) 0.7764(6) 0.7281(3) 0.0169(13) Uani 1 1 d . . .
O5 O 0.3953(5) 0.5962(5) 0.2802(4) 0.0186(14) Uani 1 1 d U . .
O6 O 0.2794(5) 0.5733(5) 0.1578(3) 0.0167(14) Uani 1 1 d . . .
O7 O 0.4334(6) 0.8166(5) 0.2334(3) 0.0235(15) Uani 1 1 d . . .
O8 O 0.3282(5) 0.7915(5) 0.1071(4) 0.0206(15) Uani 1 1 d . . .
O9 O 0.4445(5) 0.3629(5) 0.5698(4) 0.0217(15) Uani 1 1 d . . .
O10 O 0.6296(5) 0.2727(5) 0.5822(3) 0.0178(13) Uani 1 1 d . . .
O11 O 0.3616(5) 0.1822(5) 0.4752(4) 0.0167(13) Uani 1 1 d . . .
O12 O 0.5453(5) 0.0962(5) 0.4868(4) 0.0157(13) Uani 1 1 d . . .
O13 O 0.4871(6) 0.9303(4) 0.3709(4) 0.0275(15) Uani 1 1 d . . .
H131 H 0.5061 0.9861 0.4060 0.041 Uiso 1 1 d R . .
H132 H 0.4937 0.9768 0.3265 0.041 Uiso 1 1 d R . .
O14 O 0.5679(6) 0.5517(5) 0.4122(4) 0.0294(16) Uani 1 1 d . . .
H141 H 0.6247 0.5069 0.3934 0.044 Uiso 1 1 d R . .
H142 H 0.5323 0.5178 0.4560 0.044 Uiso 1 1 d R . .
O15 O 0.3145(6) 0.3837(5) 0.3634(4) 0.0282(16) Uani 1 1 d . . .
H151 H 0.3307 0.4465 0.3353 0.042 Uiso 1 1 d R . .
H152 H 0.3303 0.3270 0.3283 0.042 Uiso 1 1 d R . .
O16 O 0.2199(7) 0.9629(6) 0.4525(5) 0.047(2) Uani 1 1 d . . .
H161 H 0.2458 1.0319 0.4621 0.071 Uiso 1 1 d R . .
H162 H 0.2525 0.8996 0.4706 0.071 Uiso 1 1 d R . .
P1 P 0.2713(2) 0.66679(17) 0.51905(12) 0.0096(4) 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
C1 C2 1.340(14) . ?
C1 N1 1.351(11) . ?
C1 H1 0.9300 . ?
C2 C3 1.383(15) . ?
C2 H2 0.9300 . ?
C3 C4 1.386(12) . ?
C3 H3 0.9300 . ?
C4 C5 1.376(11) . ?
C4 H4 0.9300 . ?
C5 N1 1.365(10) . ?
C5 C6 1.456(11) . ?
C6 P1 1.836(7) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 O6 1.239(9) . ?
C7 O5 1.258(9) . ?
C7 C8 1.533(11) . ?
C8 O7 1.223(9) . ?
C8 O8 1.255(9) . ?
C9 O9 1.249(9) . ?
C9 O10 1.252(9) . ?
C9 C10 1.568(10) . ?
C10 O12 1.240(9) . ?
C10 O11 1.244(9) . ?
Lu1 O1 2.159(5) . ?
Lu1 O3 2.185(5) 3_566 ?
Lu1 O14 2.266(6) . ?
Lu1 O4 2.269(5) 3_566 ?
Lu1 O13 2.285(5) . ?
Lu1 O7 2.341(5) . ?
Lu1 O5 2.353(5) . ?
Lu2 O2 2.178(5) . ?
Lu2 O15 2.285(5) . ?
Lu2 O9 2.288(6) . ?
Lu2 O12 2.313(5) 3_456 ?
Lu2 O11 2.341(5) . ?
Lu2 O10 2.370(5) 3_456 ?
Lu2 O8 2.372(5) 2_565 ?
Lu2 O6 2.399(5) 2_565 ?
N1 O4 1.350(8) . ?
O1 P1 1.528(6) . ?
O2 P1 1.505(5) . ?
O3 P1 1.513(6) . ?
O3 Lu1 2.185(5) 3_466 ?
O4 Lu1 2.269(5) 3_466 ?
O6 Lu2 2.399(5) 2_564 ?
O8 Lu2 2.372(5) 2_564 ?
O10 Lu2 2.370(5) 3_556 ?
O12 Lu2 2.313(5) 3_556 ?
O13 H131 0.8500 . ?
O13 H132 0.8499 . ?
O14 H141 0.8500 . ?
O14 H142 0.8500 . ?
O15 H151 0.8500 . ?
O15 H152 0.8500 . ?
O16 H161 0.8500 . ?
O16 H162 0.8500 . ?

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
C2 C1 N1 120.0(9) . . ?
C2 C1 H1 120.0 . . ?
N1 C1 H1 120.0 . . ?
C1 C2 C3 121.4(10) . . ?
C1 C2 H2 119.3 . . ?
C3 C2 H2 119.3 . . ?
C2 C3 C4 116.9(10) . . ?
C2 C3 H3 121.5 . . ?
C4 C3 H3 121.5 . . ?
C5 C4 C3 122.4(10) . . ?
C5 C4 H4 118.8 . . ?
C3 C4 H4 118.8 . . ?
N1 C5 C4 116.8(9) . . ?
N1 C5 C6 118.5(7) . . ?
C4 C5 C6 124.6(8) . . ?
C5 C6 P1 113.8(6) . . ?
C5 C6 H6A 108.8 . . ?
P1 C6 H6A 108.8 . . ?
C5 C6 H6B 108.8 . . ?
P1 C6 H6B 108.8 . . ?
H6A C6 H6B 107.7 . . ?
O6 C7 O5 126.1(8) . . ?
O6 C7 C8 117.1(7) . . ?
O5 C7 C8 116.8(7) . . ?
O7 C8 O8 126.6(8) . . ?
O7 C8 C7 116.6(7) . . ?
O8 C8 C7 116.8(7) . . ?
O9 C9 O10 129.9(8) . . ?
O9 C9 C10 115.5(7) . . ?
O10 C9 C10 114.6(7) . . ?
O12 C10 O11 127.7(7) . . ?
O12 C10 C9 115.9(7) . . ?
O11 C10 C9 116.3(7) . . ?
O1 Lu1 O3 97.5(2) . 3_566 ?
O1 Lu1 O14 94.4(2) . . ?
O3 Lu1 O14 78.5(2) 3_566 . ?
O1 Lu1 O4 179.0(2) . 3_566 ?
O3 Lu1 O4 83.46(19) 3_566 3_566 ?
O14 Lu1 O4 85.6(2) . 3_566 ?
O1 Lu1 O13 82.3(2) . . ?
O3 Lu1 O13 79.8(2) 3_566 . ?
O14 Lu1 O13 157.4(2) . . ?
O4 Lu1 O13 98.0(2) 3_566 . ?
O1 Lu1 O7 102.5(2) . . ?
O3 Lu1 O7 136.3(2) 3_566 . ?
O14 Lu1 O7 137.0(2) . . ?
O4 Lu1 O7 76.8(2) 3_566 . ?
O13 Lu1 O7 65.1(2) . . ?
O1 Lu1 O5 86.3(2) . . ?
O3 Lu1 O5 151.7(2) 3_566 . ?
O14 Lu1 O5 73.3(2) . . ?
O4 Lu1 O5 92.8(2) 3_566 . ?
O13 Lu1 O5 128.4(2) . . ?
O7 Lu1 O5 68.7(2) . . ?
O2 Lu2 O15 73.30(19) . . ?
O2 Lu2 O9 87.4(2) . . ?
O15 Lu2 O9 95.4(2) . . ?
O2 Lu2 O12 78.6(2) . 3_456 ?
O15 Lu2 O12 106.3(2) . 3_456 ?
O9 Lu2 O12 149.3(2) . 3_456 ?
O2 Lu2 O11 140.7(2) . . ?
O15 Lu2 O11 77.2(2) . . ?
O9 Lu2 O11 70.1(2) . . ?
O12 Lu2 O11 135.29(19) 3_456 . ?
O2 Lu2 O10 123.9(2) . 3_456 ?
O15 Lu2 O10 74.2(2) . 3_456 ?
O9 Lu2 O10 140.1(2) . 3_456 ?
O12 Lu2 O10 68.37(18) 3_456 3_456 ?
O11 Lu2 O10 70.12(19) . 3_456 ?
O2 Lu2 O8 141.85(19) . 2_565 ?
O15 Lu2 O8 143.04(19) . 2_565 ?
O9 Lu2 O8 97.0(2) . 2_565 ?
O12 Lu2 O8 78.7(2) 3_456 2_565 ?
O11 Lu2 O8 74.6(2) . 2_565 ?
O10 Lu2 O8 74.04(19) 3_456 2_565 ?
O2 Lu2 O6 76.96(18) . 2_565 ?
O15 Lu2 O6 149.12(19) . 2_565 ?
O9 Lu2 O6 75.0(2) . 2_565 ?
O12 Lu2 O6 75.34(19) 3_456 2_565 ?
O11 Lu2 O6 124.05(19) . 2_565 ?
O10 Lu2 O6 131.34(18) 3_456 2_565 ?
O8 Lu2 O6 67.84(18) 2_565 2_565 ?
O4 N1 C1 117.1(7) . . ?
O4 N1 C5 120.4(7) . . ?
C1 N1 C5 122.3(8) . . ?
P1 O1 Lu1 143.8(4) . . ?
P1 O2 Lu2 155.9(3) . . ?
P1 O3 Lu1 143.9(3) . 3_466 ?
N1 O4 Lu1 125.3(4) . 3_466 ?
C7 O5 Lu1 117.8(5) . . ?
C7 O6 Lu2 117.2(5) . 2_564 ?
C8 O7 Lu1 119.8(5) . . ?
C8 O8 Lu2 117.9(5) . 2_564 ?
C9 O9 Lu2 120.1(5) . . ?
C9 O10 Lu2 114.2(5) . 3_556 ?
C10 O11 Lu2 117.9(5) . . ?
C10 O12 Lu2 116.5(5) . 3_556 ?
Lu1 O13 H131 138.0 . . ?
Lu1 O13 H132 126.2 . . ?
H131 O13 H132 89.1 . . ?
Lu1 O14 H141 131.1 . . ?
Lu1 O14 H142 121.2 . . ?
H141 O14 H142 107.7 . . ?
Lu2 O15 H151 130.9 . . ?
Lu2 O15 H152 121.3 . . ?
H151 O15 H152 107.7 . . ?
H161 O16 H162 127.0 . . ?
O2 P1 O3 113.5(3) . . ?
O2 P1 O1 111.6(3) . . ?
O3 P1 O1 110.1(3) . . ?
O2 P1 C6 107.1(3) . . ?
O3 P1 C6 107.4(3) . . ?
O1 P1 C6 106.8(4) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O16 H161 O11 0.85 2.14 2.962(9) 163.0 1_565
O16 H162 O3 0.85 2.48 3.075(9) 127.9 .
O15 H152 O4 0.85 1.90 2.723(8) 162.1 2_564
O15 H151 O5 0.85 2.02 2.865(8) 170.6 .
O14 H142 O9 0.85 2.63 3.455(9) 164.7 .
O14 H141 O8 0.85 2.52 3.198(8) 137.7 4_645
O13 H132 O5 0.85 2.41 3.203(8) 154.8 4_655
O13 H131 O12 0.85 1.79 2.640(7) 175.7 1_565

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.764
_refine_diff_density_min         -1.511
_refine_diff_density_rms         0.170
