# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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
_database_code_depnum_ccdc_archive 'CCDC 1035242'
_audit_update_record             
;
2014-11-20 deposited with the CCDC.
2015-01-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H11 Dy N O9 P S'
_chemical_formula_sum            'C9 H11 Dy N O9 P S'
_chemical_formula_weight         502.72

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'
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'
S S 0.1246 0.1234 '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'
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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.792(3)
_cell_length_b                   7.596(4)
_cell_length_c                   13.368(6)
_cell_angle_alpha                90.362(8)
_cell_angle_beta                 93.280(7)
_cell_angle_gamma                102.383(7)
_cell_volume                     672.4(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2741
_cell_measurement_theta_min      2.746
_cell_measurement_theta_max      28.515

_exptl_crystal_description       sheet-like
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.483
_exptl_crystal_F_000             482
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    5.879
_shelx_estimated_absorpt_T_min   0.591
_shelx_estimated_absorpt_T_max   0.758
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.710
_exptl_absorpt_correction_T_max  0.758
_exptl_absorpt_process_details   'SADABS(Bruker, 2000)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4832
_diffrn_reflns_av_unetI/netI     0.0483
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.526
_diffrn_reflns_theta_max         28.515
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             3299
_reflns_number_gt                3004
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'SMART (Bruker, 2000)'
_computing_cell_refinement       SMART
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_structure_solution    'SHELXTL (Bruker, 2000)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0624P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3299
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0354
_refine_ls_wR_factor_ref         0.0936
_refine_ls_wR_factor_gt          0.0910
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Dy1 Dy 0.29351(3) 0.76583(3) 0.45616(2) 0.01265(9) Uani 1 1 d . . . . .
P1 P 0.24451(19) 0.38457(17) 0.61967(10) 0.0131(3) Uani 1 1 d . . . . .
S1 S 0.39840(19) 1.07315(17) 0.30765(10) 0.0159(3) Uani 1 1 d . . . . .
C1 C 0.2337(8) 0.3912(7) 0.7568(4) 0.0172(10) Uani 1 1 d . . . . .
C2 C 0.1858(9) 0.2340(8) 0.8124(5) 0.0240(12) Uani 1 1 d . . . . .
H2 H 0.1534 0.1222 0.7797 0.029 Uiso 1 1 calc R U . . .
C3 C 0.1866(9) 0.2440(8) 0.9155(5) 0.0255(12) Uani 1 1 d . . . . .
H3 H 0.1578 0.1387 0.9520 0.031 Uiso 1 1 calc R U . . .
C4 C 0.2305(8) 0.4120(8) 0.9656(4) 0.0220(11) Uani 1 1 d . . . . .
C5 C 0.2306(10) 0.4311(9) 1.0714(5) 0.0302(13) Uani 1 1 d . . . . .
H5 H 0.2023 0.3296 1.1111 0.036 Uiso 1 1 calc R U . . .
C6 C 0.2728(9) 0.6006(10) 1.1148(5) 0.0319(15) Uani 1 1 d . . . . .
H6 H 0.2751 0.6129 1.1842 0.038 Uiso 1 1 calc R U . . .
C7 C 0.3120(10) 0.7535(9) 1.0570(5) 0.0322(14) Uani 1 1 d . . . . .
H7 H 0.3372 0.8664 1.0884 0.039 Uiso 1 1 calc R U . . .
C8 C 0.3146(9) 0.7428(8) 0.9540(5) 0.0277(13) Uani 1 1 d . . . . .
H8 H 0.3425 0.8464 0.9160 0.033 Uiso 1 1 calc R U . . .
C9 C 0.2734(8) 0.5691(8) 0.9079(4) 0.0207(11) Uani 1 1 d . . . . .
N1 N 0.2748(7) 0.5493(6) 0.8058(3) 0.0173(9) Uani 1 1 d . . . . .
H1A H 0.3043 0.6454 0.7711 0.021 Uiso 1 1 calc R U . . .
O1 O 0.2530(6) 0.5763(5) 0.5892(3) 0.0198(8) Uani 1 1 d . . . . .
O2 O 0.4296(5) 0.3142(5) 0.6007(3) 0.0208(8) Uani 1 1 d . . . . .
O3 O 0.0506(5) 0.2553(5) 0.5833(3) 0.0185(8) Uani 1 1 d . . . . .
O4 O 0.2797(6) 0.8879(5) 0.2881(3) 0.0225(8) Uani 1 1 d . . . . .
O5 O 0.4350(6) 1.0821(5) 0.4206(3) 0.0180(7) Uani 1 1 d . . . . .
O6 O 0.2932(7) 1.2100(6) 0.2725(4) 0.0309(10) Uani 1 1 d . . . . .
O7 O 0.5944(6) 1.0987(5) 0.2608(3) 0.0221(8) Uani 1 1 d . . . . .
O1W O 0.1722(6) 0.4777(5) 0.3709(3) 0.0248(9) Uani 1 1 d . . . . .
H1WA H 0.2218 0.4032 0.3364 0.037 Uiso 1 1 d R U . . .
H1WB H 0.0690 0.4213 0.4008 0.037 Uiso 1 1 d R U . . .
O2W O 0.1399(6) 0.9148(6) 0.5814(3) 0.0231(8) Uani 1 1 d . . . . .
H2WA H 0.1044 0.8401 0.6283 0.035 Uiso 1 1 d R U . . .
H2WB H 0.2265 1.0078 0.6054 0.035 Uiso 1 1 d R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Dy1 O2 2.265(4) 2_666 ?
Dy1 O1 2.287(4) . ?
Dy1 O3 2.337(4) 2_566 ?
Dy1 O2W 2.420(4) . ?
Dy1 O1W 2.420(4) . ?
Dy1 O4 2.440(4) . ?
Dy1 O5 2.449(4) . ?
Dy1 O5 2.482(4) 2_676 ?
P1 O1 1.505(4) . ?
P1 O2 1.501(4) . ?
P1 O3 1.517(4) . ?
P1 C1 1.840(6) . ?
S1 O6 1.448(4) . ?
S1 O4 1.478(4) . ?
S1 O7 1.479(4) . ?
S1 O5 1.515(4) . ?
C1 N1 1.332(7) . ?
C1 C2 1.398(8) . ?
C2 C3 1.380(9) . ?
C2 H2 0.9300 . ?
C3 C4 1.403(8) . ?
C3 H3 0.9300 . ?
C4 C9 1.411(8) . ?
C4 C5 1.421(8) . ?
C5 C6 1.375(9) . ?
C5 H5 0.9300 . ?
C6 C7 1.385(10) . ?
C6 H6 0.9300 . ?
C7 C8 1.380(9) . ?
C7 H7 0.9300 . ?
C8 C9 1.418(8) . ?
C8 H8 0.9300 . ?
C9 N1 1.374(7) . ?
N1 H1A 0.8600 . ?
O2 Dy1 2.265(4) 2_666 ?
O3 Dy1 2.337(4) 2_566 ?
O5 Dy1 2.482(4) 2_676 ?
O1W H1WA 0.8608 . ?
O1W H1WB 0.8603 . ?
O2W H2WA 0.8578 . ?
O2W H2WB 0.8631 . ?

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
O2 Dy1 O1 97.25(15) 2_666 . ?
O2 Dy1 O3 142.20(14) 2_666 2_566 ?
O1 Dy1 O3 96.11(15) . 2_566 ?
O2 Dy1 O2W 149.62(14) 2_666 . ?
O1 Dy1 O2W 74.09(15) . . ?
O3 Dy1 O2W 68.18(13) 2_566 . ?
O2 Dy1 O1W 74.17(14) 2_666 . ?
O1 Dy1 O1W 79.11(15) . . ?
O3 Dy1 O1W 73.92(13) 2_566 . ?
O2W Dy1 O1W 130.13(14) . . ?
O2 Dy1 O4 81.52(15) 2_666 . ?
O1 Dy1 O4 162.95(14) . . ?
O3 Dy1 O4 75.63(14) 2_566 . ?
O2W Dy1 O4 115.09(15) . . ?
O1W Dy1 O4 84.24(15) . . ?
O2 Dy1 O5 90.33(14) 2_666 . ?
O1 Dy1 O5 139.61(13) . . ?
O3 Dy1 O5 101.81(13) 2_566 . ?
O2W Dy1 O5 79.48(14) . . ?
O1W Dy1 O5 140.63(15) . . ?
O4 Dy1 O5 57.41(12) . . ?
O2 Dy1 O5 77.65(14) 2_666 2_676 ?
O1 Dy1 O5 77.41(13) . 2_676 ?
O3 Dy1 O5 139.94(13) 2_566 2_676 ?
O2W Dy1 O5 72.06(13) . 2_676 ?
O1W Dy1 O5 140.36(14) . 2_676 ?
O4 Dy1 O5 118.54(13) . 2_676 ?
O5 Dy1 O5 65.57(15) . 2_676 ?
O1 P1 O2 115.1(2) . . ?
O1 P1 O3 113.5(2) . . ?
O2 P1 O3 112.8(2) . . ?
O1 P1 C1 104.2(2) . . ?
O2 P1 C1 105.4(2) . . ?
O3 P1 C1 104.5(2) . . ?
O6 S1 O4 113.0(3) . . ?
O6 S1 O7 109.3(3) . . ?
O4 S1 O7 110.4(2) . . ?
O6 S1 O5 111.4(3) . . ?
O4 S1 O5 103.3(2) . . ?
O7 S1 O5 109.2(2) . . ?
N1 C1 C2 118.3(5) . . ?
N1 C1 P1 119.7(4) . . ?
C2 C1 P1 121.9(4) . . ?
C3 C2 C1 120.3(5) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 120.4(6) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C9 118.3(5) . . ?
C3 C4 C5 123.0(6) . . ?
C9 C4 C5 118.6(6) . . ?
C6 C5 C4 119.5(6) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C5 C6 C7 121.1(6) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C8 C7 C6 121.8(6) . . ?
C8 C7 H7 119.1 . . ?
C6 C7 H7 119.1 . . ?
C7 C8 C9 118.0(6) . . ?
C7 C8 H8 121.0 . . ?
C9 C8 H8 121.0 . . ?
N1 C9 C4 118.2(5) . . ?
N1 C9 C8 120.8(5) . . ?
C4 C9 C8 121.0(6) . . ?
C1 N1 C9 124.4(5) . . ?
C1 N1 H1A 117.8 . . ?
C9 N1 H1A 117.8 . . ?
P1 O1 Dy1 143.5(2) . . ?
P1 O2 Dy1 169.1(3) . 2_666 ?
P1 O3 Dy1 143.4(2) . 2_566 ?
S1 O4 Dy1 100.1(2) . . ?
S1 O5 Dy1 98.61(18) . . ?
S1 O5 Dy1 136.8(2) . 2_676 ?
Dy1 O5 Dy1 114.43(15) . 2_676 ?
Dy1 O1W H1WA 137.4 . . ?
Dy1 O1W H1WB 107.6 . . ?
H1WA O1W H1WB 110.4 . . ?
Dy1 O2W H2WA 108.4 . . ?
Dy1 O2W H2WB 109.3 . . ?
H2WA O2W H2WB 109.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 P1 C1 N1 -13.3(5) . . . . ?
O2 P1 C1 N1 108.3(4) . . . . ?
O3 P1 C1 N1 -132.7(4) . . . . ?
O1 P1 C1 C2 167.6(5) . . . . ?
O2 P1 C1 C2 -70.9(5) . . . . ?
O3 P1 C1 C2 48.2(5) . . . . ?
N1 C1 C2 C3 -1.6(9) . . . . ?
P1 C1 C2 C3 177.6(5) . . . . ?
C1 C2 C3 C4 1.6(9) . . . . ?
C2 C3 C4 C9 0.0(9) . . . . ?
C2 C3 C4 C5 179.0(6) . . . . ?
C3 C4 C5 C6 -179.2(6) . . . . ?
C9 C4 C5 C6 -0.2(9) . . . . ?
C4 C5 C6 C7 1.1(10) . . . . ?
C5 C6 C7 C8 -1.4(10) . . . . ?
C6 C7 C8 C9 0.7(10) . . . . ?
C3 C4 C9 N1 -1.6(8) . . . . ?
C5 C4 C9 N1 179.4(5) . . . . ?
C3 C4 C9 C8 178.6(6) . . . . ?
C5 C4 C9 C8 -0.4(8) . . . . ?
C7 C8 C9 N1 -179.6(6) . . . . ?
C7 C8 C9 C4 0.2(9) . . . . ?
C2 C1 N1 C9 -0.1(8) . . . . ?
P1 C1 N1 C9 -179.2(4) . . . . ?
C4 C9 N1 C1 1.7(8) . . . . ?
C8 C9 N1 C1 -178.6(5) . . . . ?
O2 P1 O1 Dy1 58.4(5) . . . . ?
O3 P1 O1 Dy1 -73.7(4) . . . . ?
C1 P1 O1 Dy1 173.3(4) . . . . ?
O1 P1 O2 Dy1 -43.2(14) . . . 2_666 ?
O3 P1 O2 Dy1 89.3(13) . . . 2_666 ?
C1 P1 O2 Dy1 -157.4(13) . . . 2_666 ?
O1 P1 O3 Dy1 -30.4(5) . . . 2_566 ?
O2 P1 O3 Dy1 -163.6(4) . . . 2_566 ?
C1 P1 O3 Dy1 82.5(4) . . . 2_566 ?
O6 S1 O4 Dy1 -127.0(2) . . . . ?
O7 S1 O4 Dy1 110.2(2) . . . . ?
O5 S1 O4 Dy1 -6.5(2) . . . . ?
O6 S1 O5 Dy1 128.0(2) . . . . ?
O4 S1 O5 Dy1 6.4(2) . . . . ?
O7 S1 O5 Dy1 -111.1(2) . . . . ?
O6 S1 O5 Dy1 -91.4(4) . . . 2_676 ?
O4 S1 O5 Dy1 147.0(3) . . . 2_676 ?
O7 S1 O5 Dy1 29.5(4) . . . 2_676 ?

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
O2W H2WB O2 0.86 2.44 3.242(6) 154.7 1_565
O1W H1WB O1 0.86 2.20 2.909(6) 139.3 2_566
O1W H1WA O6 0.86 1.86 2.710(6) 169.4 1_545
N1 H1A O7 0.86 1.98 2.799(6) 159.7 2_676
N1 H1A O1 0.86 2.47 2.901(6) 111.5 .
C8 H8 O7 0.93 2.45 3.164(8) 133.7 2_676

_refine_diff_density_max         3.478
_refine_diff_density_min         -1.291
_refine_diff_density_rms         0.265

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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
_database_code_depnum_ccdc_archive 'CCDC 1035243'
_audit_update_record             
;
2014-11-20 deposited with the CCDC.
2015-01-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H11 Dy N O9 P S'
_chemical_formula_sum            'C9 H11 Dy N O9 P S'
_chemical_formula_weight         502.72

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   13.3163(5)
_cell_length_b                   6.7704(3)
_cell_length_c                   15.0967(6)
_cell_angle_alpha                90
_cell_angle_beta                 90.6391(6)
_cell_angle_gamma                90
_cell_volume                     1360.98(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6084
_cell_measurement_theta_min      2.698
_cell_measurement_theta_max      28.339

_exptl_crystal_description       rod-like
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.453
_exptl_crystal_F_000             964
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    5.809
_shelx_estimated_absorpt_T_min   0.205
_shelx_estimated_absorpt_T_max   0.654
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.250
_exptl_absorpt_correction_T_max  0.628
_exptl_absorpt_process_details   'SADABS(Bruker, 2000)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7759
_diffrn_reflns_av_unetI/netI     0.0144
_diffrn_reflns_av_R_equivalents  0.0136
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.529
_diffrn_reflns_theta_max         25.995
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2678
_reflns_number_gt                2492
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'SMART (Bruker, 2000)'
_computing_cell_refinement       SMART
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_structure_solution    'SHELXTL (Bruker, 2000)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0198P)²+3.3814P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2678
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0188
_refine_ls_R_factor_gt           0.0170
_refine_ls_wR_factor_ref         0.0415
_refine_ls_wR_factor_gt          0.0405
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Dy1 Dy 0.45477(2) 0.12185(2) 0.38012(2) 0.01271(5) Uani 1 1 d . . . . .
P1 P 0.62081(5) 0.12716(10) 0.19576(5) 0.01276(14) Uani 1 1 d . . . . .
S1 S 0.30691(5) 0.08976(13) 0.53466(5) 0.02226(17) Uani 1 1 d . . . . .
C1 C 0.7585(2) 0.1333(4) 0.19753(19) 0.0175(6) Uani 1 1 d . . . . .
C2 C 0.8142(2) 0.1349(5) 0.1189(2) 0.0274(7) Uani 1 1 d . . . . .
H2 H 0.7813 0.1339 0.0642 0.033 Uiso 1 1 calc R U . . .
C3 C 0.9171(3) 0.1380(6) 0.1229(2) 0.0299(8) Uani 1 1 d . . . . .
H3 H 0.9535 0.1395 0.0707 0.036 Uiso 1 1 calc R U . . .
C4 C 0.9684(2) 0.1388(5) 0.2048(2) 0.0244(7) Uani 1 1 d . . . . .
C5 C 1.0749(2) 0.1401(5) 0.2136(3) 0.0315(8) Uani 1 1 d . . . . .
H5 H 1.1145 0.1415 0.1633 0.038 Uiso 1 1 calc R U . . .
C6 C 1.1188(3) 0.1391(6) 0.2951(3) 0.0345(8) Uani 1 1 d . . . . .
H6 H 1.1884 0.1399 0.3001 0.041 Uiso 1 1 calc R U . . .
C7 C 1.0603(3) 0.1370(6) 0.3723(3) 0.0344(8) Uani 1 1 d . . . . .
H7 H 1.0919 0.1374 0.4275 0.041 Uiso 1 1 calc R U . . .
C8 C 0.9580(2) 0.1344(5) 0.3669(2) 0.0293(8) Uani 1 1 d . . . . .
H8 H 0.9198 0.1315 0.4181 0.035 Uiso 1 1 calc R U . . .
C9 C 0.9111(2) 0.1360(5) 0.2829(2) 0.0220(6) Uani 1 1 d . . . . .
N1 N 0.80812(18) 0.1340(4) 0.27483(17) 0.0191(5) Uani 1 1 d . . . . .
H1A H 0.7735 0.1332 0.3226 0.023 Uiso 1 1 calc R U . . .
O1 O 0.59155(15) 0.1619(3) 0.29110(13) 0.0223(5) Uani 1 1 d . . . . .
O3 O 0.59056(16) 0.2937(3) 0.13429(13) 0.0185(4) Uani 1 1 d . . . . .
O2 O 0.59480(18) -0.0727(3) 0.16081(16) 0.0276(5) Uani 1 1 d . . . . .
O4 O 0.28813(17) 0.1496(4) 0.44176(14) 0.0280(5) Uani 1 1 d . . . . .
O5 O 0.41899(14) 0.0642(3) 0.53835(13) 0.0179(4) Uani 1 1 d . . . . .
O7 O 0.25954(19) -0.1030(4) 0.55370(16) 0.0393(7) Uani 1 1 d . . . . .
O6 O 0.2751(2) 0.2339(5) 0.59827(18) 0.0487(8) Uani 1 1 d . . . . .
O1W O 0.37601(17) 0.0807(3) 0.23603(14) 0.0246(5) Uani 1 1 d . . . . .
H1WA H 0.3883 -0.0289 0.2109 0.030 Uiso 1 1 d R U . . .
H1WB H 0.3584 0.1675 0.1983 0.030 Uiso 1 1 d R U . . .
O2W O 0.56109(19) 0.3551(3) 0.46072(17) 0.0315(5) Uani 1 1 d . . . . .
H2WA H 0.6212 0.3632 0.4424 0.038 Uiso 1 1 d R U . . .
H2WB H 0.5602 0.3493 0.5170 0.038 Uiso 1 1 d R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Dy1 O2 2.255(2) 2_655 ?
Dy1 O1 2.292(2) . ?
Dy1 O3 2.312(2) 2_645 ?
Dy1 O1W 2.420(2) . ?
Dy1 O4 2.423(2) . ?
Dy1 O5 2.425(2) 3_656 ?
Dy1 O2W 2.437(2) . ?
Dy1 O5 2.472(2) . ?
P1 O2 1.492(2) . ?
P1 O3 1.512(2) . ?
P1 O1 1.514(2) . ?
P1 C1 1.834(3) . ?
S1 O6 1.436(3) . ?
S1 O4 1.478(2) . ?
S1 O7 1.479(3) . ?
S1 O5 1.503(2) . ?
C1 N1 1.334(4) . ?
C1 C2 1.407(4) . ?
C2 C3 1.370(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.407(5) . ?
C3 H3 0.9300 . ?
C4 C9 1.411(5) . ?
C4 C5 1.423(4) . ?
C5 C6 1.355(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.408(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.364(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.408(4) . ?
C8 H8 0.9300 . ?
C9 N1 1.375(4) . ?
N1 H1A 0.8600 . ?
O3 Dy1 2.312(2) 2_655 ?
O2 Dy1 2.255(2) 2_645 ?
O5 Dy1 2.425(2) 3_656 ?
O1W H1WA 0.8500 . ?
O1W H1WB 0.8500 . ?
O2W H2WA 0.8516 . ?
O2W H2WB 0.8504 . ?

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
O2 Dy1 O1 87.88(9) 2_655 . ?
O2 Dy1 O3 141.28(8) 2_655 2_645 ?
O1 Dy1 O3 105.48(8) . 2_645 ?
O2 Dy1 O1W 74.74(8) 2_655 . ?
O1 Dy1 O1W 79.97(8) . . ?
O3 Dy1 O1W 72.22(7) 2_645 . ?
O2 Dy1 O4 76.57(9) 2_655 . ?
O1 Dy1 O4 162.42(8) . . ?
O3 Dy1 O4 82.60(8) 2_645 . ?
O1W Dy1 O4 87.97(8) . . ?
O2 Dy1 O5 144.54(8) 2_655 3_656 ?
O1 Dy1 O5 78.94(7) . 3_656 ?
O3 Dy1 O5 74.18(7) 2_645 3_656 ?
O1W Dy1 O5 133.41(7) . 3_656 ?
O4 Dy1 O5 118.55(7) . 3_656 ?
O2 Dy1 O2W 73.09(8) 2_655 . ?
O1 Dy1 O2W 75.83(9) . . ?
O3 Dy1 O2W 145.02(7) 2_645 . ?
O1W Dy1 O2W 140.06(8) . . ?
O4 Dy1 O2W 106.70(9) . . ?
O5 Dy1 O2W 71.81(8) 3_656 . ?
O2 Dy1 O5 110.52(8) 2_655 . ?
O1 Dy1 O5 138.45(7) . . ?
O3 Dy1 O5 83.47(7) 2_645 . ?
O1W Dy1 O5 139.81(7) . . ?
O4 Dy1 O5 56.90(7) . . ?
O5 Dy1 O5 64.38(8) 3_656 . ?
O2W Dy1 O5 74.75(8) . . ?
O2 P1 O3 113.58(13) . . ?
O2 P1 O1 114.58(14) . . ?
O3 P1 O1 113.47(12) . . ?
O2 P1 C1 104.71(14) . . ?
O3 P1 C1 104.56(13) . . ?
O1 P1 C1 104.51(13) . . ?
O6 S1 O4 113.60(17) . . ?
O6 S1 O7 109.87(18) . . ?
O4 S1 O7 110.98(15) . . ?
O6 S1 O5 110.70(15) . . ?
O4 S1 O5 102.94(12) . . ?
O7 S1 O5 108.47(15) . . ?
N1 C1 C2 118.5(3) . . ?
N1 C1 P1 119.8(2) . . ?
C2 C1 P1 121.6(2) . . ?
C3 C2 C1 119.9(3) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 120.9(3) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C3 C4 C9 118.2(3) . . ?
C3 C4 C5 123.8(3) . . ?
C9 C4 C5 118.0(3) . . ?
C6 C5 C4 120.3(3) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C7 120.9(3) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C8 C7 C6 120.8(3) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C7 C8 C9 119.1(3) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
N1 C9 C8 120.8(3) . . ?
N1 C9 C4 118.3(3) . . ?
C8 C9 C4 120.9(3) . . ?
C1 N1 C9 124.1(3) . . ?
C1 N1 H1A 118.0 . . ?
C9 N1 H1A 118.0 . . ?
P1 O1 Dy1 138.94(13) . . ?
P1 O3 Dy1 147.33(12) . 2_655 ?
P1 O2 Dy1 174.20(16) . 2_645 ?
S1 O4 Dy1 101.37(11) . . ?
S1 O5 Dy1 139.55(12) . 3_656 ?
S1 O5 Dy1 98.52(10) . . ?
Dy1 O5 Dy1 115.62(8) 3_656 . ?
Dy1 O1W H1WA 114.7 . . ?
Dy1 O1W H1WB 129.5 . . ?
H1WA O1W H1WB 111.0 . . ?
Dy1 O2W H2WA 115.0 . . ?
Dy1 O2W H2WB 117.0 . . ?
H2WA O2W H2WB 110.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 P1 C1 N1 -110.7(3) . . . . ?
O3 P1 C1 N1 129.6(2) . . . . ?
O1 P1 C1 N1 10.1(3) . . . . ?
O2 P1 C1 C2 68.5(3) . . . . ?
O3 P1 C1 C2 -51.2(3) . . . . ?
O1 P1 C1 C2 -170.7(3) . . . . ?
N1 C1 C2 C3 -0.3(5) . . . . ?
P1 C1 C2 C3 -179.5(3) . . . . ?
C1 C2 C3 C4 0.2(6) . . . . ?
C2 C3 C4 C9 0.1(5) . . . . ?
C2 C3 C4 C5 179.4(4) . . . . ?
C3 C4 C5 C6 -179.5(4) . . . . ?
C9 C4 C5 C6 -0.2(5) . . . . ?
C4 C5 C6 C7 0.0(6) . . . . ?
C5 C6 C7 C8 0.5(6) . . . . ?
C6 C7 C8 C9 -0.7(6) . . . . ?
C7 C8 C9 N1 -179.8(3) . . . . ?
C7 C8 C9 C4 0.5(5) . . . . ?
C3 C4 C9 N1 -0.4(5) . . . . ?
C5 C4 C9 N1 -179.8(3) . . . . ?
C3 C4 C9 C8 179.3(3) . . . . ?
C5 C4 C9 C8 -0.1(5) . . . . ?
C2 C1 N1 C9 -0.1(5) . . . . ?
P1 C1 N1 C9 179.1(2) . . . . ?
C8 C9 N1 C1 -179.3(3) . . . . ?
C4 C9 N1 C1 0.4(5) . . . . ?
O2 P1 O1 Dy1 -48.4(2) . . . . ?
O3 P1 O1 Dy1 84.3(2) . . . . ?
C1 P1 O1 Dy1 -162.44(19) . . . . ?
O2 P1 O3 Dy1 153.4(2) . . . 2_655 ?
O1 P1 O3 Dy1 20.2(3) . . . 2_655 ?
C1 P1 O3 Dy1 -93.1(2) . . . 2_655 ?
O6 S1 O4 Dy1 124.47(16) . . . . ?
O7 S1 O4 Dy1 -111.14(15) . . . . ?
O5 S1 O4 Dy1 4.73(14) . . . . ?
O6 S1 O5 Dy1 85.5(2) . . . 3_656 ?
O4 S1 O5 Dy1 -152.77(19) . . . 3_656 ?
O7 S1 O5 Dy1 -35.1(2) . . . 3_656 ?
O6 S1 O5 Dy1 -126.32(16) . . . . ?
O4 S1 O5 Dy1 -4.59(14) . . . . ?
O7 S1 O5 Dy1 113.05(12) . . . . ?

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
O1W H1WA O1 0.85 2.11 2.898(3) 153.8 2_645
N1 H1A O1 0.86 2.47 2.903(3) 111.8 .
N1 H1A O1 0.86 2.47 2.903(3) 111.8 .
O1W H1WA O1 0.85 2.11 2.898(3) 153.8 2_645

_refine_diff_density_max         1.101
_refine_diff_density_min         -0.577
_refine_diff_density_rms         0.091

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_Y
_database_code_depnum_ccdc_archive 'CCDC 1035244'
_audit_update_record             
;
2014-11-20 deposited with the CCDC.
2015-01-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H11 N O9 P S Y'
_chemical_formula_sum            'C9 H11 N O9 P S Y'
_chemical_formula_weight         429.13

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'
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'
S S 0.1246 0.1234 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Y Y -2.7962 3.5667 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.778(3)
_cell_length_b                   7.572(3)
_cell_length_c                   13.356(5)
_cell_angle_alpha                90.423(6)
_cell_angle_beta                 93.298(7)
_cell_angle_gamma                102.310(6)
_cell_volume                     668.4(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    747
_cell_measurement_theta_min      2.754
_cell_measurement_theta_max      25.344

_exptl_crystal_description       sheet-like
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.132
_exptl_crystal_F_000             428
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    4.687
_shelx_estimated_absorpt_T_min   0.651
_shelx_estimated_absorpt_T_max   0.799
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.755
_exptl_absorpt_correction_T_max  0.799
_exptl_absorpt_process_details   'SADABS(Bruker, 2000)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4878
_diffrn_reflns_av_unetI/netI     0.0989
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.527
_diffrn_reflns_theta_max         28.464
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             3311
_reflns_number_gt                2444
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'SMART (Bruker, 2000)'
_computing_cell_refinement       SMART
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_structure_solution    'SHELXTL (Bruker, 2000)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0785P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3311
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0885
_refine_ls_R_factor_gt           0.0601
_refine_ls_wR_factor_ref         0.1533
_refine_ls_wR_factor_gt          0.1378
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Y1 Y 0.29334(8) 0.76591(7) 0.45639(4) 0.01372(17) Uani 1 1 d . . . . .
P1 P 0.2451(2) 0.38475(19) 0.61875(11) 0.0136(3) Uani 1 1 d . . . . .
S1 S 0.3967(2) 1.07150(19) 0.30800(10) 0.0166(3) Uani 1 1 d . . . . .
C1 C 0.2334(9) 0.3909(8) 0.7566(4) 0.0185(12) Uani 1 1 d . . . . .
C2 C 0.1858(10) 0.2342(9) 0.8126(5) 0.0252(14) Uani 1 1 d . . . . .
H2 H 0.1541 0.1221 0.7798 0.030 Uiso 1 1 calc R U . . .
C3 C 0.1849(10) 0.2425(9) 0.9135(5) 0.0258(14) Uani 1 1 d . . . . .
H3 H 0.1550 0.1361 0.9493 0.031 Uiso 1 1 calc R U . . .
C4 C 0.2289(10) 0.4116(9) 0.9657(4) 0.0230(13) Uani 1 1 d . . . . .
C5 C 0.2294(11) 0.4319(10) 1.0710(5) 0.0282(15) Uani 1 1 d . . . . .
H5 H 0.2013 0.3301 1.1106 0.034 Uiso 1 1 calc R U . . .
C6 C 0.2707(11) 0.5998(10) 1.1147(5) 0.0340(17) Uani 1 1 d . . . . .
H6 H 0.2709 0.6118 1.1841 0.041 Uiso 1 1 calc R U . . .
C7 C 0.3126(11) 0.7536(10) 1.0567(5) 0.0341(17) Uani 1 1 d . . . . .
H7 H 0.3401 0.8668 1.0883 0.041 Uiso 1 1 calc R U . . .
C8 C 0.3145(11) 0.7429(9) 0.9547(5) 0.0292(15) Uani 1 1 d . . . . .
H8 H 0.3411 0.8469 0.9168 0.035 Uiso 1 1 calc R U . . .
C9 C 0.2746(9) 0.5678(9) 0.9077(5) 0.0208(13) Uani 1 1 d . . . . .
N1 N 0.2761(8) 0.5495(7) 0.8053(4) 0.0183(10) Uani 1 1 d . . . . .
H1A H 0.3062 0.6460 0.7708 0.022 Uiso 1 1 calc R U . . .
O1 O 0.2540(7) 0.5781(5) 0.5889(3) 0.0201(9) Uani 1 1 d . . . . .
O2 O 0.4301(6) 0.3140(6) 0.6001(3) 0.0203(9) Uani 1 1 d . . . . .
O3 O 0.0509(6) 0.2572(5) 0.5839(3) 0.0195(9) Uani 1 1 d . . . . .
O4 O 0.2781(7) 0.8866(6) 0.2882(3) 0.0230(10) Uani 1 1 d . . . . .
O5 O 0.4343(6) 1.0808(5) 0.4204(3) 0.0174(9) Uani 1 1 d . . . . .
O6 O 0.2896(8) 1.2075(6) 0.2732(3) 0.0320(11) Uani 1 1 d . . . . .
O7 O 0.5937(7) 1.0974(6) 0.2610(3) 0.0230(10) Uani 1 1 d . . . . .
O1W O 0.1718(7) 0.4791(6) 0.3717(3) 0.0263(10) Uani 1 1 d . . . . .
H1WA H 0.2213 0.4046 0.3372 0.040 Uiso 1 1 d R U . . .
H1WB H 0.0686 0.4227 0.4016 0.040 Uiso 1 1 d R U . . .
O2W O 0.1397(6) 0.9151(6) 0.5810(3) 0.0223(9) Uani 1 1 d . . . . .
H2WA H 0.1042 0.8404 0.6279 0.033 Uiso 1 1 d R U . . .
H2WB H 0.2263 1.0081 0.6050 0.033 Uiso 1 1 d R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Y1 O2 2.256(4) 2_666 ?
Y1 O1 2.270(4) . ?
Y1 O3 2.333(4) 2_566 ?
Y1 O1W 2.402(4) . ?
Y1 O2W 2.409(4) . ?
Y1 O5 2.435(4) . ?
Y1 O4 2.436(4) . ?
Y1 O5 2.484(4) 2_676 ?
P1 O2 1.497(4) . ?
P1 O3 1.504(4) . ?
P1 O1 1.510(4) . ?
P1 C1 1.848(6) . ?
S1 O6 1.446(5) . ?
S1 O4 1.472(4) . ?
S1 O7 1.484(4) . ?
S1 O5 1.507(4) . ?
C1 N1 1.330(8) . ?
C1 C2 1.396(9) . ?
C2 C3 1.349(9) . ?
C2 H2 0.9300 . ?
C3 C4 1.419(9) . ?
C3 H3 0.9300 . ?
C4 C9 1.407(9) . ?
C4 C5 1.414(8) . ?
C5 C6 1.362(10) . ?
C5 H5 0.9300 . ?
C6 C7 1.391(10) . ?
C6 H6 0.9300 . ?
C7 C8 1.365(9) . ?
C7 H7 0.9300 . ?
C8 C9 1.428(9) . ?
C8 H8 0.9300 . ?
C9 N1 1.374(7) . ?
N1 H1A 0.8600 . ?
O2 Y1 2.256(4) 2_666 ?
O3 Y1 2.333(4) 2_566 ?
O5 Y1 2.484(4) 2_676 ?
O1W H1WA 0.8584 . ?
O1W H1WB 0.8594 . ?
O2W H2WA 0.8569 . ?
O2W H2WB 0.8612 . ?

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
O2 Y1 O1 97.24(15) 2_666 . ?
O2 Y1 O3 141.85(15) 2_666 2_566 ?
O1 Y1 O3 96.20(15) . 2_566 ?
O2 Y1 O1W 74.43(15) 2_666 . ?
O1 Y1 O1W 79.27(15) . . ?
O3 Y1 O1W 73.29(15) 2_566 . ?
O2 Y1 O2W 149.63(15) 2_666 . ?
O1 Y1 O2W 74.09(15) . . ?
O3 Y1 O2W 68.52(14) 2_566 . ?
O1W Y1 O2W 129.95(15) . . ?
O2 Y1 O5 90.14(15) 2_666 . ?
O1 Y1 O5 139.64(14) . . ?
O3 Y1 O5 102.11(14) 2_566 . ?
O1W Y1 O5 140.44(14) . . ?
O2W Y1 O5 79.66(14) . . ?
O2 Y1 O4 81.58(15) 2_666 . ?
O1 Y1 O4 162.87(14) . . ?
O3 Y1 O4 75.37(15) 2_566 . ?
O1W Y1 O4 83.99(15) . . ?
O2W Y1 O4 115.08(15) . . ?
O5 Y1 O4 57.47(13) . . ?
O2 Y1 O5 77.56(14) 2_666 2_676 ?
O1 Y1 O5 77.37(14) . 2_676 ?
O3 Y1 O5 140.38(14) 2_566 2_676 ?
O1W Y1 O5 140.60(15) . 2_676 ?
O2W Y1 O5 72.16(14) . 2_676 ?
O5 Y1 O5 65.57(16) . 2_676 ?
O4 Y1 O5 118.66(13) . 2_676 ?
O2 P1 O3 113.5(2) . . ?
O2 P1 O1 115.2(2) . . ?
O3 P1 O1 113.6(2) . . ?
O2 P1 C1 105.3(3) . . ?
O3 P1 C1 103.5(3) . . ?
O1 P1 C1 104.0(3) . . ?
O6 S1 O4 112.4(3) . . ?
O6 S1 O7 109.7(3) . . ?
O4 S1 O7 110.5(3) . . ?
O6 S1 O5 111.5(3) . . ?
O4 S1 O5 103.6(2) . . ?
O7 S1 O5 109.0(2) . . ?
N1 C1 C2 118.2(5) . . ?
N1 C1 P1 119.3(4) . . ?
C2 C1 P1 122.4(5) . . ?
C3 C2 C1 121.2(6) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C2 C3 C4 120.7(6) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C9 C4 C5 118.7(6) . . ?
C9 C4 C3 117.1(6) . . ?
C5 C4 C3 124.2(6) . . ?
C6 C5 C4 120.3(6) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C7 120.7(6) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C8 C7 C6 121.8(7) . . ?
C8 C7 H7 119.1 . . ?
C6 C7 H7 119.1 . . ?
C7 C8 C9 118.3(6) . . ?
C7 C8 H8 120.9 . . ?
C9 C8 H8 120.9 . . ?
N1 C9 C4 119.1(6) . . ?
N1 C9 C8 120.6(6) . . ?
C4 C9 C8 120.3(6) . . ?
C1 N1 C9 123.6(5) . . ?
C1 N1 H1A 118.2 . . ?
C9 N1 H1A 118.2 . . ?
P1 O1 Y1 143.0(2) . . ?
P1 O2 Y1 169.0(3) . 2_666 ?
P1 O3 Y1 144.4(2) . 2_566 ?
S1 O4 Y1 99.7(2) . . ?
S1 O5 Y1 98.71(19) . . ?
S1 O5 Y1 136.9(2) . 2_676 ?
Y1 O5 Y1 114.43(16) . 2_676 ?
Y1 O1W H1WA 137.2 . . ?
Y1 O1W H1WB 107.7 . . ?
H1WA O1W H1WB 110.4 . . ?
Y1 O2W H2WA 108.3 . . ?
Y1 O2W H2WB 109.2 . . ?
H2WA O2W H2WB 109.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 P1 C1 N1 107.8(5) . . . . ?
O3 P1 C1 N1 -132.8(5) . . . . ?
O1 P1 C1 N1 -13.8(5) . . . . ?
O2 P1 C1 C2 -70.7(6) . . . . ?
O3 P1 C1 C2 48.7(6) . . . . ?
O1 P1 C1 C2 167.8(5) . . . . ?
N1 C1 C2 C3 -0.7(10) . . . . ?
P1 C1 C2 C3 177.8(5) . . . . ?
C1 C2 C3 C4 1.1(10) . . . . ?
C2 C3 C4 C9 -0.5(10) . . . . ?
C2 C3 C4 C5 179.4(7) . . . . ?
C9 C4 C5 C6 0.8(10) . . . . ?
C3 C4 C5 C6 -179.1(7) . . . . ?
C4 C5 C6 C7 0.1(11) . . . . ?
C5 C6 C7 C8 -0.1(12) . . . . ?
C6 C7 C8 C9 -0.8(11) . . . . ?
C5 C4 C9 N1 179.5(6) . . . . ?
C3 C4 C9 N1 -0.5(9) . . . . ?
C5 C4 C9 C8 -1.8(10) . . . . ?
C3 C4 C9 C8 178.1(6) . . . . ?
C7 C8 C9 N1 -179.6(6) . . . . ?
C7 C8 C9 C4 1.8(10) . . . . ?
C2 C1 N1 C9 -0.4(9) . . . . ?
P1 C1 N1 C9 -179.0(4) . . . . ?
C4 C9 N1 C1 1.0(9) . . . . ?
C8 C9 N1 C1 -177.6(6) . . . . ?
O2 P1 O1 Y1 59.2(5) . . . . ?
O3 P1 O1 Y1 -74.2(5) . . . . ?
C1 P1 O1 Y1 173.9(4) . . . . ?
O3 P1 O2 Y1 90.2(14) . . . 2_666 ?
O1 P1 O2 Y1 -43.3(15) . . . 2_666 ?
C1 P1 O2 Y1 -157.3(13) . . . 2_666 ?
O2 P1 O3 Y1 -162.8(4) . . . 2_566 ?
O1 P1 O3 Y1 -28.6(5) . . . 2_566 ?
C1 P1 O3 Y1 83.6(5) . . . 2_566 ?
O6 S1 O4 Y1 -126.8(2) . . . . ?
O7 S1 O4 Y1 110.3(2) . . . . ?
O5 S1 O4 Y1 -6.3(3) . . . . ?
O6 S1 O5 Y1 127.4(3) . . . . ?
O4 S1 O5 Y1 6.3(3) . . . . ?
O7 S1 O5 Y1 -111.4(2) . . . . ?
O6 S1 O5 Y1 -91.7(4) . . . 2_676 ?
O4 S1 O5 Y1 147.2(3) . . . 2_676 ?
O7 S1 O5 Y1 29.6(4) . . . 2_676 ?

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
O2W H2WB O2 0.86 2.43 3.234(6) 154.7 1_565
O1W H1WB O1 0.86 2.20 2.905(6) 139.7 2_566
O1W H1WA O6 0.86 1.87 2.716(6) 168.6 1_545
N1 H1A O7 0.86 1.97 2.798(6) 160.0 2_676
N1 H1A O1 0.86 2.47 2.898(6) 111.5 .
N1 H1A S1 0.86 2.86 3.630(5) 150.0 2_676
C8 H8 O7 0.93 2.46 3.176(8) 133.5 2_676

_refine_diff_density_max         1.762
_refine_diff_density_min         -1.062
_refine_diff_density_rms         0.203

_shelxl_version_number           2013-4

