# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_61007Am
_database_code_depnum_ccdc_archive 'CCDC 2233015'
loop_
_audit_author_name
_audit_author_address
ab
;NanJing university
China
;
_audit_update_record             
;
2022-12-27 deposited with the CCDC.	2023-07-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H11 La N O9 P S'
_chemical_formula_sum            'C9 H11 La N O9 P S'
_chemical_formula_weight         479.13

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'
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'
La La -0.2871 2.4523 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-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                   8.5067(19)
_cell_length_b                   12.250(3)
_cell_length_c                   26.474(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2758.8(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    881
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      27.6

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.307
_exptl_crystal_F_000             1856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    3.412
_shelx_estimated_absorpt_T_min   0.611
_shelx_estimated_absorpt_T_max   0.647
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.585
_exptl_absorpt_correction_T_max  0.647
_exptl_absorpt_process_details   'SADABS(Bruker, 2000)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13735
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.846
_diffrn_reflns_theta_max         25.987
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2700
_reflns_number_gt                2473
_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)+(0.0490P)²+52.1512P] 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         2700
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0545
_refine_ls_wR_factor_ref         0.1264
_refine_ls_wR_factor_gt          0.1222
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001

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
La1 La 0.25558(5) 0.44252(3) 0.48926(2) 0.01453(16) Uani 1 1 d . . . . .
P1 P -0.0098(2) 0.31106(15) 0.55745(7) 0.0139(4) Uani 1 1 d . . . . .
S1 S 0.4572(2) 0.55045(15) 0.39843(7) 0.0164(4) Uani 1 1 d . . . . .
C1 C -0.0436(9) 0.3163(7) 0.6256(3) 0.0188(16) Uani 1 1 d . . . . .
C2 C 0.0009(12) 0.4037(8) 0.6561(3) 0.031(2) Uani 1 1 d . . . . .
H2A H 0.0465 0.4654 0.6418 0.038 Uiso 1 1 calc R U . . .
C3 C -0.0228(12) 0.3985(8) 0.7070(3) 0.036(2) Uani 1 1 d . . . . .
H3A H 0.0105 0.4559 0.7273 0.043 Uiso 1 1 calc R U . . .
C4 C -0.0967(11) 0.3078(7) 0.7291(3) 0.029(2) Uani 1 1 d . . . . .
C5 C -0.1250(13) 0.2989(9) 0.7821(4) 0.041(3) Uani 1 1 d . . . . .
H5A H -0.0947 0.3544 0.8040 0.049 Uiso 1 1 calc R U . . .
C6 C -0.1973(15) 0.2074(9) 0.7998(4) 0.045(3) Uani 1 1 d . . . . .
H6A H -0.2146 0.2007 0.8343 0.054 Uiso 1 1 calc R U . . .
C7 C -0.2460(13) 0.1241(10) 0.7683(4) 0.045(3) Uani 1 1 d . . . . .
H7A H -0.2971 0.0638 0.7819 0.053 Uiso 1 1 calc R U . . .
C8 C -0.2202(12) 0.1290(9) 0.7172(4) 0.037(2) Uani 1 1 d . . . . .
H8A H -0.2528 0.0725 0.6962 0.044 Uiso 1 1 calc R U . . .
C9 C -0.1437(10) 0.2208(7) 0.6973(3) 0.0252(19) Uani 1 1 d . . . . .
N1 N -0.1121(8) 0.2303(5) 0.6468(2) 0.0187(14) Uani 1 1 d . . . . .
H1C H -0.1418 0.1718 0.6278 0.022 Uiso 1 1 d R U . . .
O1 O 0.1663(7) 0.3010(5) 0.5509(2) 0.0223(13) Uani 1 1 d . . . . .
O2 O -0.0588(7) 0.4198(5) 0.5364(2) 0.0247(13) Uani 1 1 d . . . . .
O3 O -0.1020(7) 0.2143(5) 0.5409(2) 0.0243(13) Uani 1 1 d . . . . .
O4 O 0.3180(7) 0.4786(5) 0.3956(2) 0.0219(12) Uani 1 1 d . . . . .
O5 O 0.4935(6) 0.5571(4) 0.4538(2) 0.0178(11) Uani 1 1 d . . . . .
O6 O 0.4197(8) 0.6575(5) 0.3789(2) 0.0283(14) Uani 1 1 d . . . . .
O7 O 0.5878(7) 0.5010(5) 0.3711(2) 0.0264(14) Uani 1 1 d . . . . .
O1W O 0.0681(7) 0.3421(5) 0.4341(2) 0.0278(14) Uani 1 1 d . . . . .
H1WA H 0.0870 0.2814 0.4150 0.033 Uiso 1 1 d R U . . .
H1WB H -0.0304 0.3705 0.4340 0.033 Uiso 1 1 d R U . . .
O2W O 0.2363(6) 0.5932(5) 0.5578(2) 0.0237(13) Uani 1 1 d . . . . .
H2WA H 0.2596 0.6630 0.5476 0.028 Uiso 1 1 d R U . . .
H2WB H 0.2827 0.5666 0.5859 0.028 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
La1 O3 2.407(5) 4_556 ?
La1 O2 2.472(6) 5_566 ?
La1 O1W 2.488(6) . ?
La1 O1 2.500(6) . ?
La1 O4 2.573(6) . ?
La1 O2W 2.594(5) . ?
La1 O5 2.613(6) 5_666 ?
La1 O5 2.636(5) . ?
La1 O2 2.965(6) . ?
La1 S1 3.236(2) . ?
La1 P1 3.309(2) . ?
P1 O3 1.487(6) . ?
P1 O2 1.503(6) . ?
P1 O1 1.513(6) . ?
P1 C1 1.827(8) . ?
S1 O6 1.446(6) . ?
S1 O7 1.457(6) . ?
S1 O4 1.477(6) . ?
S1 O5 1.500(6) . ?
C1 N1 1.328(10) . ?
C1 C2 1.394(12) . ?
C2 C3 1.364(13) . ?
C2 H2A 0.9300 . ?
C3 C4 1.405(14) . ?
C3 H3A 0.9300 . ?
C4 C9 1.417(12) . ?
C4 C5 1.426(13) . ?
C5 C6 1.363(16) . ?
C5 H5A 0.9300 . ?
C6 C7 1.380(16) . ?
C6 H6A 0.9300 . ?
C7 C8 1.371(13) . ?
C7 H7A 0.9300 . ?
C8 C9 1.402(13) . ?
C8 H8A 0.9300 . ?
C9 N1 1.368(10) . ?
N1 H1C 0.9118 . ?
O2 La1 2.472(6) 5_566 ?
O3 La1 2.407(5) 4_456 ?
O5 La1 2.613(5) 5_666 ?
O1W H1WA 0.9133 . ?
O1W H1WB 0.9071 . ?
O2W H2WA 0.9187 . ?
O2W H2WB 0.9015 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 La1 O2 142.58(19) 4_556 5_566 ?
O3 La1 O1W 74.6(2) 4_556 . ?
O2 La1 O1W 75.0(2) 5_566 . ?
O3 La1 O1 79.38(19) 4_556 . ?
O2 La1 O1 116.57(19) 5_566 . ?
O1W La1 O1 81.1(2) . . ?
O3 La1 O4 73.37(19) 4_556 . ?
O2 La1 O4 75.97(19) 5_566 . ?
O1W La1 O4 69.60(19) . . ?
O1 La1 O4 144.18(18) . . ?
O3 La1 O2W 146.26(18) 4_556 . ?
O2 La1 O2W 70.38(18) 5_566 . ?
O1W La1 O2W 136.23(18) . . ?
O1 La1 O2W 91.00(19) . . ?
O4 La1 O2W 124.40(19) . . ?
O3 La1 O5 77.38(18) 4_556 5_666 ?
O2 La1 O5 135.29(18) 5_566 5_666 ?
O1W La1 O5 149.69(18) . 5_666 ?
O1 La1 O5 82.69(17) . 5_666 ?
O4 La1 O5 112.74(17) . 5_666 ?
O2W La1 O5 69.30(16) . 5_666 ?
O3 La1 O5 85.43(18) 4_556 . ?
O2 La1 O5 93.37(18) 5_566 . ?
O1W La1 O5 123.10(19) . . ?
O1 La1 O5 146.64(18) . . ?
O4 La1 O5 53.62(17) . . ?
O2W La1 O5 85.35(17) . . ?
O5 La1 O5 64.98(19) 5_666 . ?
O3 La1 O2 121.26(19) 4_556 . ?
O2 La1 O2 64.5(2) 5_566 . ?
O1W La1 O2 67.85(18) . . ?
O1 La1 O2 52.10(17) . . ?
O4 La1 O2 127.46(17) . . ?
O2W La1 O2 73.43(17) . . ?
O5 La1 O2 119.60(16) 5_666 . ?
O5 La1 O2 153.21(16) . . ?
O3 La1 S1 79.22(15) 4_556 . ?
O2 La1 S1 82.86(14) 5_566 . ?
O1W La1 S1 96.04(15) . . ?
O1 La1 S1 158.39(13) . . ?
O4 La1 S1 26.44(13) . . ?
O2W La1 S1 105.23(14) . . ?
O5 La1 S1 89.70(12) 5_666 . ?
O5 La1 S1 27.23(12) . . ?
O2 La1 S1 146.05(11) . . ?
O3 La1 P1 97.81(15) 4_556 . ?
O2 La1 P1 91.15(14) 5_566 . ?
O1W La1 P1 69.06(15) . . ?
O1 La1 P1 25.69(13) . . ?
O4 La1 P1 138.59(13) . . ?
O2W La1 P1 85.49(14) . . ?
O5 La1 P1 104.09(12) 5_666 . ?
O5 La1 P1 167.78(12) . . ?
O2 La1 P1 27.01(11) . . ?
S1 La1 P1 164.99(5) . . ?
O3 P1 O2 116.8(3) . . ?
O3 P1 O1 115.0(3) . . ?
O2 P1 O1 107.7(3) . . ?
O3 P1 C1 103.7(4) . . ?
O2 P1 C1 106.9(3) . . ?
O1 P1 C1 105.7(3) . . ?
O3 P1 La1 125.9(2) . . ?
O2 P1 La1 63.6(2) . . ?
O1 P1 La1 45.7(2) . . ?
C1 P1 La1 129.0(3) . . ?
O6 S1 O7 111.6(4) . . ?
O6 S1 O4 110.2(4) . . ?
O7 S1 O4 109.8(4) . . ?
O6 S1 O5 110.3(3) . . ?
O7 S1 O5 110.5(3) . . ?
O4 S1 O5 104.2(3) . . ?
O6 S1 La1 121.3(3) . . ?
O7 S1 La1 127.1(2) . . ?
O4 S1 La1 50.9(2) . . ?
O5 S1 La1 53.5(2) . . ?
N1 C1 C2 118.9(7) . . ?
N1 C1 P1 117.3(6) . . ?
C2 C1 P1 123.8(6) . . ?
C3 C2 C1 119.7(9) . . ?
C3 C2 H2A 120.1 . . ?
C1 C2 H2A 120.1 . . ?
C2 C3 C4 121.0(8) . . ?
C2 C3 H3A 119.5 . . ?
C4 C3 H3A 119.5 . . ?
C3 C4 C9 118.2(8) . . ?
C3 C4 C5 123.1(9) . . ?
C9 C4 C5 118.7(9) . . ?
C6 C5 C4 118.4(9) . . ?
C6 C5 H5A 120.8 . . ?
C4 C5 H5A 120.8 . . ?
C5 C6 C7 122.4(9) . . ?
C5 C6 H6A 118.8 . . ?
C7 C6 H6A 118.8 . . ?
C8 C7 C6 121.0(11) . . ?
C8 C7 H7A 119.5 . . ?
C6 C7 H7A 119.5 . . ?
C7 C8 C9 118.7(10) . . ?
C7 C8 H8A 120.6 . . ?
C9 C8 H8A 120.6 . . ?
N1 C9 C8 121.9(8) . . ?
N1 C9 C4 117.5(8) . . ?
C8 C9 C4 120.7(8) . . ?
C1 N1 C9 124.6(7) . . ?
C1 N1 H1C 120.8 . . ?
C9 N1 H1C 114.6 . . ?
P1 O1 La1 108.6(3) . . ?
P1 O2 La1 153.5(4) . 5_566 ?
P1 O2 La1 89.4(3) . . ?
La1 O2 La1 115.5(2) 5_566 . ?
P1 O3 La1 177.5(4) . 4_456 ?
S1 O4 La1 102.7(3) . . ?
S1 O5 La1 137.0(3) . 5_666 ?
S1 O5 La1 99.3(3) . . ?
La1 O5 La1 115.02(19) 5_666 . ?
La1 O1W H1WA 127.9 . . ?
La1 O1W H1WB 113.8 . . ?
H1WA O1W H1WB 118.2 . . ?
La1 O2W H2WA 116.3 . . ?
La1 O2W H2WB 106.9 . . ?
H2WA O2W H2WB 119.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 P1 C1 N1 11.3(7) . . . . ?
O2 P1 C1 N1 135.3(6) . . . . ?
O1 P1 C1 N1 -110.0(6) . . . . ?
La1 P1 C1 N1 -155.2(5) . . . . ?
O3 P1 C1 C2 -169.9(7) . . . . ?
O2 P1 C1 C2 -45.9(8) . . . . ?
O1 P1 C1 C2 68.7(8) . . . . ?
La1 P1 C1 C2 23.5(9) . . . . ?
N1 C1 C2 C3 1.6(14) . . . . ?
P1 C1 C2 C3 -177.1(7) . . . . ?
C1 C2 C3 C4 -2.3(15) . . . . ?
C2 C3 C4 C9 1.1(15) . . . . ?
C2 C3 C4 C5 -179.6(10) . . . . ?
C3 C4 C5 C6 -179.9(10) . . . . ?
C9 C4 C5 C6 -0.5(15) . . . . ?
C4 C5 C6 C7 -1.0(17) . . . . ?
C5 C6 C7 C8 1.4(18) . . . . ?
C6 C7 C8 C9 -0.3(17) . . . . ?
C7 C8 C9 N1 179.0(9) . . . . ?
C7 C8 C9 C4 -1.2(15) . . . . ?
C3 C4 C9 N1 0.8(13) . . . . ?
C5 C4 C9 N1 -178.6(8) . . . . ?
C3 C4 C9 C8 -179.0(9) . . . . ?
C5 C4 C9 C8 1.6(14) . . . . ?
C2 C1 N1 C9 0.3(12) . . . . ?
P1 C1 N1 C9 179.1(6) . . . . ?
C8 C9 N1 C1 178.3(8) . . . . ?
C4 C9 N1 C1 -1.5(12) . . . . ?
O3 P1 O1 La1 116.7(3) . . . . ?
O2 P1 O1 La1 -15.6(4) . . . . ?
C1 P1 O1 La1 -129.6(3) . . . . ?
O3 P1 O2 La1 41.6(9) . . . 5_566 ?
O1 P1 O2 La1 172.9(7) . . . 5_566 ?
C1 P1 O2 La1 -73.9(8) . . . 5_566 ?
La1 P1 O2 La1 160.5(8) . . . 5_566 ?
O3 P1 O2 La1 -118.9(3) . . . . ?
O1 P1 O2 La1 12.4(3) . . . . ?
C1 P1 O2 La1 125.6(3) . . . . ?
O6 S1 O4 La1 -114.5(3) . . . . ?
O7 S1 O4 La1 122.3(3) . . . . ?
O5 S1 O4 La1 3.8(3) . . . . ?
O6 S1 O5 La1 -101.9(5) . . . 5_666 ?
O7 S1 O5 La1 21.9(5) . . . 5_666 ?
O4 S1 O5 La1 139.8(4) . . . 5_666 ?
La1 S1 O5 La1 143.5(5) . . . 5_666 ?
O6 S1 O5 La1 114.6(3) . . . . ?
O7 S1 O5 La1 -121.6(3) . . . . ?
O4 S1 O5 La1 -3.7(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1C O4 0.91 1.97 2.857(9) 162.9 4_456
O1W H1WA O6 0.91 1.79 2.694(8) 167.9 8_655
O1W H1WB O2W 0.91 1.82 2.716(8) 169.1 5_566
O2W H2WA O1 0.92 1.81 2.683(8) 158.7 8_665
O2W H2WB O7 0.90 1.79 2.667(8) 164.1 5_666

_refine_diff_density_max         1.181
_refine_diff_density_min         -0.925
_refine_diff_density_rms         0.148

_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_51019Cm
_database_code_depnum_ccdc_archive 'CCDC 2233020'
loop_
_audit_author_name
_audit_author_address
Pr
;NanJing university
China
;
_audit_update_record             
;
2022-12-27 deposited with the CCDC.	2023-07-20 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 Pr S'
_chemical_formula_sum            'C9 H11 N O9 P Pr S'
_chemical_formula_weight         481.13

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-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                   8.4758(18)
_cell_length_b                   12.107(3)
_cell_length_c                   26.511(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2720.4(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    927
_cell_measurement_theta_min      3.03
_cell_measurement_theta_max      27.8

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.349
_exptl_crystal_F_000             1872
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.260
_exptl_absorpt_coefficient_mu    3.901
_shelx_estimated_absorpt_T_min   0.387
_shelx_estimated_absorpt_T_max   0.430
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.323
_exptl_absorpt_correction_T_max  0.356
_exptl_absorpt_process_details   'SADABS(Bruker, 2000)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13618
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.853
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2676
_reflns_number_gt                2464
_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)+(0.0417P)²+17.8766P] 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         2676
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0375
_refine_ls_wR_factor_ref         0.0890
_refine_ls_wR_factor_gt          0.0858
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001

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
Pr1 Pr 0.26007(3) 0.44308(2) 0.48847(2) 0.01554(11) Uani 1 1 d . . . . .
P1 P -0.01157(15) 0.31259(10) 0.55670(5) 0.0154(3) Uani 1 1 d . . . . .
S1 S 0.45922(15) 0.55116(10) 0.39892(5) 0.0184(3) Uani 1 1 d . . . . .
C1 C -0.0422(6) 0.3164(4) 0.6249(2) 0.0199(11) Uani 1 1 d . . . . .
C2 C 0.0046(7) 0.4047(5) 0.6553(2) 0.0297(13) Uani 1 1 d . . . . .
H2A H 0.0518 0.4665 0.6410 0.036 Uiso 1 1 calc R U . . .
C3 C -0.0192(7) 0.3997(5) 0.7061(2) 0.0320(14) Uani 1 1 d . . . . .
H3A H 0.0149 0.4578 0.7263 0.038 Uiso 1 1 calc R U . . .
C4 C -0.0941(7) 0.3086(5) 0.7284(2) 0.0287(13) Uani 1 1 d . . . . .
C5 C -0.1216(8) 0.2994(6) 0.7808(2) 0.0395(16) Uani 1 1 d . . . . .
H5A H -0.0891 0.3551 0.8026 0.047 Uiso 1 1 calc R U . . .
C6 C -0.1960(9) 0.2081(6) 0.7991(3) 0.0422(17) Uani 1 1 d . . . . .
H6A H -0.2134 0.2020 0.8337 0.051 Uiso 1 1 calc R U . . .
C7 C -0.2466(8) 0.1239(6) 0.7675(3) 0.0395(17) Uani 1 1 d . . . . .
H7A H -0.2989 0.0632 0.7810 0.047 Uiso 1 1 calc R U . . .
C8 C -0.2201(8) 0.1291(6) 0.7164(2) 0.0353(15) Uani 1 1 d . . . . .
H8A H -0.2534 0.0725 0.6953 0.042 Uiso 1 1 calc R U . . .
C9 C -0.1422(7) 0.2216(5) 0.6969(2) 0.0243(12) Uani 1 1 d . . . . .
N1 N -0.1123(5) 0.2312(4) 0.64624(17) 0.0208(10) Uani 1 1 d . . . . .
H1C H -0.1421 0.1727 0.6272 0.025 Uiso 1 1 d R U . . .
O1 O 0.1658(4) 0.3071(3) 0.54960(14) 0.0248(9) Uani 1 1 d . . . . .
O2 O -0.0698(5) 0.4204(3) 0.53678(15) 0.0312(10) Uani 1 1 d . . . . .
O3 O -0.0985(4) 0.2116(3) 0.54064(14) 0.0246(9) Uani 1 1 d . . . . .
O4 O 0.3190(5) 0.4788(3) 0.39616(14) 0.0237(8) Uani 1 1 d . . . . .
O5 O 0.4943(4) 0.5573(3) 0.45453(14) 0.0207(8) Uani 1 1 d . . . . .
O6 O 0.4236(5) 0.6600(3) 0.37944(15) 0.0297(9) Uani 1 1 d . . . . .
O7 O 0.5905(5) 0.5008(3) 0.37210(15) 0.0284(9) Uani 1 1 d . . . . .
O1W O 0.0712(4) 0.3438(3) 0.43579(15) 0.0278(9) Uani 1 1 d . . . . .
H1WA H 0.0898 0.2818 0.4175 0.033 Uiso 1 1 d R U . . .
H1WB H -0.0259 0.3743 0.4341 0.033 Uiso 1 1 d R U . . .
O2W O 0.2368(4) 0.5929(3) 0.55619(16) 0.0244(9) Uani 1 1 d . . . . .
H2WA H 0.2658 0.6613 0.5454 0.029 Uiso 1 1 d R U . . .
H2WB H 0.2883 0.5617 0.5823 0.029 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
Pr1 O3 2.354(4) 4_556 ?
Pr1 O2 2.404(4) 5_566 ?
Pr1 O1W 2.441(4) . ?
Pr1 O1 2.445(4) . ?
Pr1 O4 2.535(4) . ?
Pr1 O2W 2.560(4) . ?
Pr1 O5 2.572(4) 5_666 ?
Pr1 O5 2.581(4) . ?
Pr1 S1 3.1933(14) . ?
Pr1 P1 3.3270(14) . ?
P1 O3 1.489(4) . ?
P1 O2 1.492(4) . ?
P1 O1 1.516(4) . ?
P1 C1 1.827(6) . ?
S1 O6 1.447(4) . ?
S1 O7 1.455(4) . ?
S1 O4 1.478(4) . ?
S1 O5 1.506(4) . ?
C1 N1 1.318(7) . ?
C1 C2 1.396(8) . ?
C2 C3 1.363(9) . ?
C2 H2A 0.9300 . ?
C3 C4 1.404(9) . ?
C3 H3A 0.9300 . ?
C4 C9 1.404(8) . ?
C4 C5 1.412(9) . ?
C5 C6 1.362(10) . ?
C5 H5A 0.9300 . ?
C6 C7 1.388(10) . ?
C6 H6A 0.9300 . ?
C7 C8 1.374(9) . ?
C7 H7A 0.9300 . ?
C8 C9 1.399(9) . ?
C8 H8A 0.9300 . ?
C9 N1 1.373(7) . ?
N1 H1C 0.9055 . ?
O2 Pr1 2.405(4) 5_566 ?
O3 Pr1 2.354(4) 4_456 ?
O5 Pr1 2.572(4) 5_666 ?
O1W H1WA 0.9072 . ?
O1W H1WB 0.9031 . ?
O2W H2WA 0.9090 . ?
O2W H2WB 0.9006 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 Pr1 O2 142.88(14) 4_556 5_566 ?
O3 Pr1 O1W 75.79(13) 4_556 . ?
O2 Pr1 O1W 74.89(14) 5_566 . ?
O3 Pr1 O1 81.24(13) 4_556 . ?
O2 Pr1 O1 115.36(14) 5_566 . ?
O1W Pr1 O1 80.40(14) . . ?
O3 Pr1 O4 73.68(13) 4_556 . ?
O2 Pr1 O4 75.29(13) 5_566 . ?
O1W Pr1 O4 70.18(13) . . ?
O1 Pr1 O4 145.02(13) . . ?
O3 Pr1 O2W 146.41(13) 4_556 . ?
O2 Pr1 O2W 69.90(13) 5_566 . ?
O1W Pr1 O2W 134.40(12) . . ?
O1 Pr1 O2W 89.27(13) . . ?
O4 Pr1 O2W 124.84(13) . . ?
O3 Pr1 O5 77.24(12) 4_556 5_666 ?
O2 Pr1 O5 135.04(13) 5_566 5_666 ?
O1W Pr1 O5 150.00(12) . 5_666 ?
O1 Pr1 O5 82.76(12) . 5_666 ?
O4 Pr1 O5 114.08(12) . 5_666 ?
O2W Pr1 O5 69.61(11) . 5_666 ?
O3 Pr1 O5 85.43(12) 4_556 . ?
O2 Pr1 O5 92.91(14) 5_566 . ?
O1W Pr1 O5 124.67(13) . . ?
O1 Pr1 O5 147.48(12) . . ?
O4 Pr1 O5 54.59(12) . . ?
O2W Pr1 O5 85.65(12) . . ?
O5 Pr1 O5 65.37(14) 5_666 . ?
O3 Pr1 S1 79.24(10) 4_556 . ?
O2 Pr1 S1 82.30(11) 5_566 . ?
O1W Pr1 S1 97.08(10) . . ?
O1 Pr1 S1 160.32(9) . . ?
O4 Pr1 S1 26.90(9) . . ?
O2W Pr1 S1 105.77(10) . . ?
O5 Pr1 S1 90.55(9) 5_666 . ?
O5 Pr1 S1 27.73(8) . . ?
O3 Pr1 P1 98.78(10) 4_556 . ?
O2 Pr1 P1 90.78(11) 5_566 . ?
O1W Pr1 P1 67.87(10) . . ?
O1 Pr1 P1 24.98(9) . . ?
O4 Pr1 P1 137.92(9) . . ?
O2W Pr1 P1 84.37(9) . . ?
O5 Pr1 P1 103.88(8) 5_666 . ?
O5 Pr1 P1 167.46(9) . . ?
S1 Pr1 P1 164.71(3) . . ?
O3 P1 O2 116.9(2) . . ?
O3 P1 O1 114.8(2) . . ?
O2 P1 O1 108.8(3) . . ?
O3 P1 C1 103.5(2) . . ?
O2 P1 C1 106.3(2) . . ?
O1 P1 C1 105.4(2) . . ?
O3 P1 Pr1 125.21(16) . . ?
O2 P1 Pr1 67.72(19) . . ?
O1 P1 Pr1 42.90(15) . . ?
C1 P1 Pr1 128.65(18) . . ?
O6 S1 O7 111.5(2) . . ?
O6 S1 O4 110.7(2) . . ?
O7 S1 O4 110.0(2) . . ?
O6 S1 O5 110.2(2) . . ?
O7 S1 O5 110.4(2) . . ?
O4 S1 O5 103.7(2) . . ?
O6 S1 Pr1 121.89(18) . . ?
O7 S1 Pr1 126.58(17) . . ?
O4 S1 Pr1 50.88(15) . . ?
O5 S1 Pr1 52.90(14) . . ?
N1 C1 C2 118.6(5) . . ?
N1 C1 P1 118.0(4) . . ?
C2 C1 P1 123.4(4) . . ?
C3 C2 C1 119.6(6) . . ?
C3 C2 H2A 120.2 . . ?
C1 C2 H2A 120.2 . . ?
C2 C3 C4 121.2(6) . . ?
C2 C3 H3A 119.4 . . ?
C4 C3 H3A 119.4 . . ?
C9 C4 C3 118.0(5) . . ?
C9 C4 C5 118.5(6) . . ?
C3 C4 C5 123.5(6) . . ?
C6 C5 C4 119.4(6) . . ?
C6 C5 H5A 120.3 . . ?
C4 C5 H5A 120.3 . . ?
C5 C6 C7 121.6(6) . . ?
C5 C6 H6A 119.2 . . ?
C7 C6 H6A 119.2 . . ?
C8 C7 C6 120.7(7) . . ?
C8 C7 H7A 119.6 . . ?
C6 C7 H7A 119.6 . . ?
C7 C8 C9 118.5(6) . . ?
C7 C8 H8A 120.7 . . ?
C9 C8 H8A 120.7 . . ?
N1 C9 C8 121.1(5) . . ?
N1 C9 C4 117.8(5) . . ?
C8 C9 C4 121.2(5) . . ?
C1 N1 C9 124.7(5) . . ?
C1 N1 H1C 119.9 . . ?
C9 N1 H1C 115.3 . . ?
P1 O1 Pr1 112.1(2) . . ?
P1 O2 Pr1 157.2(3) . 5_566 ?
P1 O3 Pr1 177.1(3) . 4_456 ?
S1 O4 Pr1 102.22(19) . . ?
S1 O5 Pr1 137.3(2) . 5_666 ?
S1 O5 Pr1 99.37(18) . . ?
Pr1 O5 Pr1 114.63(13) 5_666 . ?
Pr1 O1W H1WA 126.8 . . ?
Pr1 O1W H1WB 115.1 . . ?
H1WA O1W H1WB 118.1 . . ?
Pr1 O2W H2WA 113.8 . . ?
Pr1 O2W H2WB 101.7 . . ?
H2WA O2W H2WB 119.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 P1 C1 N1 7.2(5) . . . . ?
O2 P1 C1 N1 131.0(4) . . . . ?
O1 P1 C1 N1 -113.6(4) . . . . ?
Pr1 P1 C1 N1 -154.8(3) . . . . ?
O3 P1 C1 C2 -172.8(5) . . . . ?
O2 P1 C1 C2 -49.0(5) . . . . ?
O1 P1 C1 C2 66.4(5) . . . . ?
Pr1 P1 C1 C2 25.2(6) . . . . ?
N1 C1 C2 C3 1.7(9) . . . . ?
P1 C1 C2 C3 -178.4(5) . . . . ?
C1 C2 C3 C4 -1.8(10) . . . . ?
C2 C3 C4 C9 0.9(9) . . . . ?
C2 C3 C4 C5 180.0(6) . . . . ?
C9 C4 C5 C6 -1.3(10) . . . . ?
C3 C4 C5 C6 179.7(6) . . . . ?
C4 C5 C6 C7 -0.4(11) . . . . ?
C5 C6 C7 C8 1.3(11) . . . . ?
C6 C7 C8 C9 -0.4(10) . . . . ?
C7 C8 C9 N1 179.9(6) . . . . ?
C7 C8 C9 C4 -1.2(9) . . . . ?
C3 C4 C9 N1 0.1(8) . . . . ?
C5 C4 C9 N1 -179.0(5) . . . . ?
C3 C4 C9 C8 -178.8(6) . . . . ?
C5 C4 C9 C8 2.1(9) . . . . ?
C2 C1 N1 C9 -0.6(8) . . . . ?
P1 C1 N1 C9 179.4(4) . . . . ?
C8 C9 N1 C1 178.7(5) . . . . ?
C4 C9 N1 C1 -0.3(8) . . . . ?
O3 P1 O1 Pr1 115.9(2) . . . . ?
O2 P1 O1 Pr1 -17.3(3) . . . . ?
C1 P1 O1 Pr1 -131.0(2) . . . . ?
O3 P1 O2 Pr1 40.0(7) . . . 5_566 ?
O1 P1 O2 Pr1 172.0(6) . . . 5_566 ?
C1 P1 O2 Pr1 -75.0(7) . . . 5_566 ?
Pr1 P1 O2 Pr1 159.3(7) . . . 5_566 ?
O6 S1 O4 Pr1 -114.8(2) . . . . ?
O7 S1 O4 Pr1 121.4(2) . . . . ?
O5 S1 O4 Pr1 3.4(2) . . . . ?
O6 S1 O5 Pr1 -101.4(3) . . . 5_666 ?
O7 S1 O5 Pr1 22.2(4) . . . 5_666 ?
O4 S1 O5 Pr1 140.0(3) . . . 5_666 ?
Pr1 S1 O5 Pr1 143.3(3) . . . 5_666 ?
O6 S1 O5 Pr1 115.3(2) . . . . ?
O7 S1 O5 Pr1 -121.1(2) . . . . ?
O4 S1 O5 Pr1 -3.3(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
N1 H1C O4 0.91 1.96 2.840(6) 162.5 4_456
O1W H1WA O6 0.91 1.79 2.681(6) 166.3 8_655
O1W H1WB O2W 0.90 1.85 2.729(5) 164.2 5_566
O2W H2WA O1 0.91 1.86 2.726(6) 158.2 8_665
O2W H2WB O7 0.90 1.76 2.654(6) 172.7 5_666

_refine_diff_density_max         0.872
_refine_diff_density_min         -0.633
_refine_diff_density_rms         0.124

_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_60908Bm
_database_code_depnum_ccdc_archive 'CCDC 2233016'
loop_
_audit_author_name
_audit_author_address
Ce
;NanJing university
China
;
_audit_update_record             
;
2022-12-27 deposited with the CCDC.	2023-07-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H11 Ce N O9 P S'
_chemical_formula_sum            'C9 H11 Ce N O9 P S'
_chemical_formula_weight         480.34

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'
Ce Ce -0.2486 2.6331 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-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                   8.4923(11)
_cell_length_b                   12.1763(15)
_cell_length_c                   26.509(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2741.1(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    905
_cell_measurement_theta_min      2.85
_cell_measurement_theta_max      18.73

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.328
_exptl_crystal_F_000             1864
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    3.638
_shelx_estimated_absorpt_T_min   0.476
_shelx_estimated_absorpt_T_max   0.530
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.434
_exptl_absorpt_correction_T_max  0.530
_exptl_absorpt_process_details   'SADABS(Bruker, 2000)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13788
_diffrn_reflns_av_unetI/netI     0.0699
_diffrn_reflns_av_R_equivalents  0.0896
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.849
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2698
_reflns_number_gt                1988
_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)+(0.0546P)²+18.9379P] 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         2698
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0913
_refine_ls_R_factor_gt           0.0609
_refine_ls_wR_factor_ref         0.1328
_refine_ls_wR_factor_gt          0.1195
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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
Ce1 Ce 0.25829(6) 0.44264(4) 0.48879(2) 0.01638(18) Uani 1 1 d . . . . .
P1 P -0.0113(3) 0.31208(18) 0.55694(9) 0.0158(5) Uani 1 1 d . . . . .
S1 S 0.4582(3) 0.55097(18) 0.39878(8) 0.0189(5) Uani 1 1 d . . . . .
C1 C -0.0429(11) 0.3167(8) 0.6256(4) 0.021(2) Uani 1 1 d . . . . .
C2 C 0.0044(13) 0.4020(8) 0.6556(4) 0.030(2) Uani 1 1 d . . . . .
H2A H 0.0542 0.4624 0.6412 0.036 Uiso 1 1 calc R U . . .
C3 C -0.0207(14) 0.3991(9) 0.7061(4) 0.037(3) Uani 1 1 d . . . . .
H3A H 0.0112 0.4578 0.7260 0.044 Uiso 1 1 calc R U . . .
C4 C -0.0949(13) 0.3075(8) 0.7287(4) 0.029(2) Uani 1 1 d . . . . .
C5 C -0.1229(15) 0.2991(9) 0.7810(4) 0.040(3) Uani 1 1 d . . . . .
H5A H -0.0926 0.3555 0.8026 0.048 Uiso 1 1 calc R U . . .
C6 C -0.1938(16) 0.2088(10) 0.7993(4) 0.043(3) Uani 1 1 d . . . . .
H6A H -0.2088 0.2025 0.8340 0.052 Uiso 1 1 calc R U . . .
C7 C -0.2465(14) 0.1231(10) 0.7674(4) 0.042(3) Uani 1 1 d . . . . .
H7A H -0.3007 0.0635 0.7809 0.050 Uiso 1 1 calc R U . . .
C8 C -0.2170(13) 0.1284(9) 0.7165(4) 0.034(3) Uani 1 1 d . . . . .
H8A H -0.2456 0.0711 0.6952 0.040 Uiso 1 1 calc R U . . .
C9 C -0.1430(12) 0.2222(9) 0.6976(4) 0.027(2) Uani 1 1 d . . . . .
N1 N -0.1114(9) 0.2304(7) 0.6467(3) 0.0231(19) Uani 1 1 d . . . . .
H1C H -0.1412 0.1719 0.6277 0.028 Uiso 1 1 d R U . . .
O1 O 0.1662(8) 0.3049(5) 0.5504(2) 0.0256(16) Uani 1 1 d . . . . .
O2 O -0.0670(9) 0.4200(5) 0.5363(3) 0.0308(17) Uani 1 1 d . . . . .
O3 O -0.1009(8) 0.2126(5) 0.5405(2) 0.0262(16) Uani 1 1 d . . . . .
O4 O 0.3188(8) 0.4788(5) 0.3959(2) 0.0243(15) Uani 1 1 d . . . . .
O5 O 0.4944(7) 0.5572(5) 0.4543(2) 0.0179(14) Uani 1 1 d . . . . .
O6 O 0.4217(9) 0.6590(5) 0.3792(2) 0.0289(17) Uani 1 1 d . . . . .
O7 O 0.5901(8) 0.5011(6) 0.3718(2) 0.0288(16) Uani 1 1 d . . . . .
O1W O 0.0698(8) 0.3431(5) 0.4345(3) 0.0306(17) Uani 1 1 d . . . . .
H1WA H 0.0823 0.2796 0.4168 0.037 Uiso 1 1 d R U . . .
H1WB H -0.0266 0.3750 0.4349 0.037 Uiso 1 1 d R U . . .
O2W O 0.2366(7) 0.5932(5) 0.5570(3) 0.0274(16) Uani 1 1 d . . . . .
H2WA H 0.2678 0.6616 0.5469 0.033 Uiso 1 1 d R U . . .
H2WB H 0.2802 0.5649 0.5852 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
Ce1 O3 2.368(6) 4_556 ?
Ce1 O2 2.425(7) 5_566 ?
Ce1 O1 2.469(7) . ?
Ce1 O1W 2.471(7) . ?
Ce1 O4 2.553(6) . ?
Ce1 O2W 2.582(6) . ?
Ce1 O5 2.586(6) 5_666 ?
Ce1 O5 2.608(6) . ?
P1 O3 1.495(6) . ?
P1 O2 1.499(7) . ?
P1 O1 1.520(7) . ?
P1 C1 1.841(10) . ?
S1 O6 1.449(6) . ?
S1 O7 1.461(7) . ?
S1 O4 1.477(7) . ?
S1 O5 1.506(6) . ?
C1 N1 1.324(12) . ?
C1 C2 1.368(13) . ?
C2 C3 1.356(14) . ?
C2 H2A 0.9300 . ?
C3 C4 1.414(14) . ?
C3 H3A 0.9300 . ?
C4 C9 1.388(14) . ?
C4 C5 1.411(14) . ?
C5 C6 1.344(16) . ?
C5 H5A 0.9300 . ?
C6 C7 1.416(16) . ?
C6 H6A 0.9300 . ?
C7 C8 1.375(14) . ?
C7 H7A 0.9300 . ?
C8 C9 1.397(15) . ?
C8 H8A 0.9300 . ?
C9 N1 1.380(12) . ?
N1 H1C 0.9087 . ?
O2 Ce1 2.425(7) 5_566 ?
O3 Ce1 2.368(6) 4_456 ?
O5 Ce1 2.586(6) 5_666 ?
O1W H1WA 0.9110 . ?
O1W H1WB 0.9055 . ?
O2W H2WA 0.9138 . ?
O2W H2WB 0.9015 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 Ce1 O2 143.0(2) 4_556 5_566 ?
O3 Ce1 O1 80.5(2) 4_556 . ?
O2 Ce1 O1 116.0(2) 5_566 . ?
O3 Ce1 O1W 75.2(2) 4_556 . ?
O2 Ce1 O1W 75.2(2) 5_566 . ?
O1 Ce1 O1W 81.2(2) . . ?
O3 Ce1 O4 73.7(2) 4_556 . ?
O2 Ce1 O4 75.6(2) 5_566 . ?
O1 Ce1 O4 145.0(2) . . ?
O1W Ce1 O4 69.7(2) . . ?
O3 Ce1 O2W 146.4(2) 4_556 . ?
O2 Ce1 O2W 69.8(2) 5_566 . ?
O1 Ce1 O2W 89.8(2) . . ?
O1W Ce1 O2W 135.3(2) . . ?
O4 Ce1 O2W 124.6(2) . . ?
O3 Ce1 O5 77.4(2) 4_556 5_666 ?
O2 Ce1 O5 134.7(2) 5_566 5_666 ?
O1 Ce1 O5 82.6(2) . 5_666 ?
O1W Ce1 O5 150.1(2) . 5_666 ?
O4 Ce1 O5 113.50(19) . 5_666 ?
O2W Ce1 O5 69.44(19) . 5_666 ?
O3 Ce1 O5 85.6(2) 4_556 . ?
O2 Ce1 O5 92.9(2) 5_566 . ?
O1 Ce1 O5 147.0(2) . . ?
O1W Ce1 O5 123.8(2) . . ?
O4 Ce1 O5 54.22(19) . . ?
O2W Ce1 O5 85.44(19) . . ?
O5 Ce1 O5 65.1(2) 5_666 . ?
O3 P1 O2 116.3(4) . . ?
O3 P1 O1 115.2(4) . . ?
O2 P1 O1 108.8(4) . . ?
O3 P1 C1 103.8(4) . . ?
O2 P1 C1 106.7(4) . . ?
O1 P1 C1 105.0(4) . . ?
O6 S1 O7 111.5(4) . . ?
O6 S1 O4 110.5(4) . . ?
O7 S1 O4 110.0(4) . . ?
O6 S1 O5 110.4(4) . . ?
O7 S1 O5 110.1(4) . . ?
O4 S1 O5 104.1(4) . . ?
N1 C1 C2 119.1(9) . . ?
N1 C1 P1 117.2(7) . . ?
C2 C1 P1 123.7(8) . . ?
C3 C2 C1 120.5(10) . . ?
C3 C2 H2A 119.8 . . ?
C1 C2 H2A 119.8 . . ?
C2 C3 C4 120.7(10) . . ?
C2 C3 H3A 119.7 . . ?
C4 C3 H3A 119.7 . . ?
C9 C4 C5 118.8(10) . . ?
C9 C4 C3 117.9(9) . . ?
C5 C4 C3 123.3(10) . . ?
C6 C5 C4 119.3(10) . . ?
C6 C5 H5A 120.4 . . ?
C4 C5 H5A 120.4 . . ?
C5 C6 C7 121.9(11) . . ?
C5 C6 H6A 119.0 . . ?
C7 C6 H6A 119.0 . . ?
C8 C7 C6 119.6(11) . . ?
C8 C7 H7A 120.2 . . ?
C6 C7 H7A 120.2 . . ?
C7 C8 C9 118.2(10) . . ?
C7 C8 H8A 120.9 . . ?
C9 C8 H8A 120.9 . . ?
N1 C9 C4 118.1(10) . . ?
N1 C9 C8 119.9(10) . . ?
C4 C9 C8 122.1(9) . . ?
C1 N1 C9 123.7(9) . . ?
C1 N1 H1C 120.7 . . ?
C9 N1 H1C 115.5 . . ?
P1 O1 Ce1 110.5(4) . . ?
P1 O2 Ce1 156.3(5) . 5_566 ?
P1 O3 Ce1 177.8(4) . 4_456 ?
S1 O4 Ce1 102.4(3) . . ?
S1 O5 Ce1 137.4(3) . 5_666 ?
S1 O5 Ce1 99.1(3) . . ?
Ce1 O5 Ce1 114.9(2) 5_666 . ?
Ce1 O1W H1WA 129.9 . . ?
Ce1 O1W H1WB 111.6 . . ?
H1WA O1W H1WB 118.4 . . ?
Ce1 O2W H2WA 114.9 . . ?
Ce1 O2W H2WB 106.2 . . ?
H2WA O2W H2WB 118.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 P1 C1 N1 9.4(8) . . . . ?
O2 P1 C1 N1 132.8(7) . . . . ?
O1 P1 C1 N1 -111.9(7) . . . . ?
O3 P1 C1 C2 -172.6(8) . . . . ?
O2 P1 C1 C2 -49.2(9) . . . . ?
O1 P1 C1 C2 66.1(9) . . . . ?
N1 C1 C2 C3 -1.0(15) . . . . ?
P1 C1 C2 C3 -179.0(8) . . . . ?
C1 C2 C3 C4 0.6(17) . . . . ?
C2 C3 C4 C9 -1.0(16) . . . . ?
C2 C3 C4 C5 179.4(11) . . . . ?
C9 C4 C5 C6 0.6(17) . . . . ?
C3 C4 C5 C6 -179.8(11) . . . . ?
C4 C5 C6 C7 -2.2(19) . . . . ?
C5 C6 C7 C8 3.8(19) . . . . ?
C6 C7 C8 C9 -3.5(17) . . . . ?
C5 C4 C9 N1 -178.5(9) . . . . ?
C3 C4 C9 N1 1.9(14) . . . . ?
C5 C4 C9 C8 -0.5(16) . . . . ?
C3 C4 C9 C8 179.9(10) . . . . ?
C7 C8 C9 N1 179.9(10) . . . . ?
C7 C8 C9 C4 2.0(16) . . . . ?
C2 C1 N1 C9 2.0(14) . . . . ?
P1 C1 N1 C9 -179.9(7) . . . . ?
C4 C9 N1 C1 -2.5(14) . . . . ?
C8 C9 N1 C1 179.4(9) . . . . ?
O3 P1 O1 Ce1 115.8(4) . . . . ?
O2 P1 O1 Ce1 -16.7(5) . . . . ?
C1 P1 O1 Ce1 -130.7(4) . . . . ?
O3 P1 O2 Ce1 41.9(11) . . . 5_566 ?
O1 P1 O2 Ce1 173.9(9) . . . 5_566 ?
C1 P1 O2 Ce1 -73.3(11) . . . 5_566 ?
O6 S1 O4 Ce1 -114.8(4) . . . . ?
O7 S1 O4 Ce1 121.7(3) . . . . ?
O5 S1 O4 Ce1 3.7(4) . . . . ?
O6 S1 O5 Ce1 -101.5(5) . . . 5_666 ?
O7 S1 O5 Ce1 22.1(6) . . . 5_666 ?
O4 S1 O5 Ce1 139.9(5) . . . 5_666 ?
O6 S1 O5 Ce1 115.0(4) . . . . ?
O7 S1 O5 Ce1 -121.4(3) . . . . ?
O4 S1 O5 Ce1 -3.6(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
O2W H2WB O7 0.90 1.78 2.655(9) 163.5 5_666
O2W H2WB S1 0.90 2.67 3.342(7) 132.6 5_666
O2W H2WA O1 0.91 1.84 2.712(10) 160.0 8_665
O1W H1WB O2W 0.91 1.84 2.724(9) 165.7 5_566
O1W H1WA O6 0.91 1.77 2.679(9) 171.7 8_655
O1W H1WA S1 0.91 2.85 3.689(7) 154.5 8_655
N1 H1C O4 0.91 1.97 2.849(11) 162.9 4_456
N1 H1C S1 0.91 2.93 3.680(8) 141.2 4_456
C8 H8A O4 0.93 2.55 3.267(12) 134.2 4_456
N1 H1C O4 0.91 1.97 2.849(11) 162.9 4_456
O1W H1WA O6 0.91 1.77 2.679(9) 171.7 8_655
O1W H1WB O2W 0.91 1.84 2.724(9) 165.7 5_566
O2W H2WA O1 0.91 1.84 2.712(10) 160.0 8_665
O2W H2WB O7 0.90 1.78 2.655(9) 163.5 5_666

_refine_diff_density_max         1.003
_refine_diff_density_min         -1.176
_refine_diff_density_rms         0.185

_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_51023A1m
_database_code_depnum_ccdc_archive 'CCDC 2233022'
loop_
_audit_author_name
_audit_author_address
Sm
;NanJing university
China
;
_audit_update_record             
;
2022-12-27 deposited with the CCDC.	2023-07-20 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2013
_audit_creation_date             2021-05-14
_chemical_formula_sum            'C9 H11 N O9 P S Sm'
_chemical_formula_weight         490.570
_refine_ls_R_factor_all          0.033
_cell_length_a                   8.4635(7)
_cell_length_b                   11.9568(11)
_cell_length_c                   26.595(2)
_cell_angle_alpha                90.000
_cell_angle_beta                 90.000
_cell_angle_gamma                90.000
_cell_volume                     2691.3(4)
_cell_formula_units_Z            8
_symmetry_int_tables_number      61
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_space_group_name_Hall  -P_2ac_2ab

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,-y,1/2+z
3 1/2+x,1/2-y,-z
4 -x,1/2+y,1/2-z
5 -x,-y,-z
6 1/2+x,y,1/2-z
7 1/2-x,1/2+y,z
8 x,1/2-y,1/2+z

loop_
_atom_type_symbol
_atom_type_oxidation_number
_atom_type_radius_bond
Sm ? 1.200
P ? 1.200
S ? 1.200
C ? 1.200
H ? 1.200
N ? 1.200
O ? 1.200


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_Wyckoff_symbol
_atom_site_attached_hydrogens
_atom_site_calc_flag
_atom_site_thermal_displace_type
_atom_site_u_iso_or_equiv
Sm1 Sm 0.2665(0) 0.4439(0) 0.4875(0) 1.000 8 c ? d Uani 0.01403(10)
P1 P -0.0126(1) 0.3150(1) 0.556() 1.000 8 c ? d Uani 0.0140(2)
S1 S 0.4625(1) 0.5520(1) 0.3996(0) 1.000 8 c ? d Uani 0.0168(2)
C1 C -0.0397(5) 0.3179(4) 0.6242(2) 1.000 8 c ? d Uani 0.0162(9)
C2 C 0.0089(7) 0.4074(5) 0.6548(2) 1.000 8 c ? d Uani 0.0295(12)
H2A H 0.0571 0.4697 0.6405 1.000 8 c ? calc Uiso 0.03500
C3 C -0.0149(7) 0.4025(5) 0.7051(2) 1.000 8 c ? d Uani 0.0342(13)
H3A H 0.0200 0.4611 0.7253 1.000 8 c ? calc Uiso 0.04100
C4 C -0.0910(6) 0.3111(4) 0.7273(2) 1.000 8 c ? d Uani 0.0264(12)
C5 C -0.1184(8) 0.3013(5) 0.7796(2) 1.000 8 c ? d Uani 0.0381(15)
H5A H -0.0841 0.3574 0.8013 1.000 8 c ? calc Uiso 0.04600
C6 C -0.1945(9) 0.2104(6) 0.7985(2) 1.000 8 c ? d Uani 0.0426(15)
H6A H -0.2119 0.2047 0.8330 1.000 8 c ? calc Uiso 0.05100
C7 C -0.2469(7) 0.1255(6) 0.7664(2) 1.000 8 c ? d Uani 0.0379(15)
H7A H -0.3005 0.0646 0.7798 1.000 8 c ? calc Uiso 0.04500
C8 C -0.2210(7) 0.1301(5) 0.7155(2) 1.000 8 c ? d Uani 0.0320(13)
H8A H -0.2555 0.0728 0.6945 1.000 8 c ? calc Uiso 0.03800
C9 C -0.1411(6) 0.2236(4) 0.6960(2) 1.000 8 c ? d Uani 0.0243(11)
N1 N -0.1110(5) 0.2319(3) 0.6455(1) 1.000 8 c ? d Uani 0.0189(8)
H1C H -0.1408 0.1733 0.6265 1.000 8 c ? d Uiso 0.02300
O1 O 0.1649(4) 0.3153(3) 0.5480(1) 1.000 8 c ? d Uani 0.0229(8)
O2 O -0.0834(5) 0.4211(3) 0.5370(1) 1.000 8 c ? d Uani 0.0312(9)
O3 O -0.0924(4) 0.2094(3) 0.5404(1) 1.000 8 c ? d Uani 0.0232(8)
O4 O 0.3217(4) 0.4791(3) 0.3965(1) 1.000 8 c ? d Uani 0.0213(7)
O5 O 0.4960(4) 0.5573(3) 0.4550(1) 1.000 8 c ? d Uani 0.0187(7)
O6 O 0.4278(5) 0.6624(3) 0.3803(1) 1.000 8 c ? d Uani 0.0287(8)
O7 O 0.5937(4) 0.4999(3) 0.3731(1) 1.000 8 c ? d Uani 0.0256(8)
O1W O 0.0753(4) 0.3464(3) 0.4377(1) 1.000 8 c ? d Uani 0.0268(8)
H1WA H 0.0889 0.2786 0.4236 1.000 8 c ? d Uiso 0.03200
H1WB H -0.0198 0.3791 0.4340 1.000 8 c ? d Uiso 0.03200
O2W O 0.2367(4) 0.5924(3) 0.5546(1) 1.000 8 c ? d Uani 0.0230(8)
H2WA H 0.2626 0.6605 0.5426 1.000 8 c ? d Uiso 0.02800
H2WB H 0.2887 0.5672 0.5818 1.000 8 c ? d Uiso 0.02800



loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Sm1 O3 . 3_556 2.310(3) no
Sm1 O2 . 5_566 2.330(4) no
Sm1 O1 . . 2.386(3) no
Sm1 O1W . . 2.394(3) no
Sm1 O4 . . 2.499(3) no
Sm1 O5 . . 2.522(3) no
Sm1 O5 . 5_666 2.527(3) no
Sm1 O2W . . 2.530(4) no
Sm1 S1 . . 3.1446(12) no
Sm1 P1 . . 3.3584(12) no
P1 O3 . . 1.490(3) no
P1 O2 . . 1.492(4) no
P1 O1 . . 1.518(3) no
P1 C1 . . 1.829(5) no
S1 O6 . . 1.447(4) no
S1 O7 . . 1.454(4) no
S1 O4 . . 1.478(4) no
S1 O5 . . 1.502(3) no
C1 N1 . . 1.320(6) no
C1 C2 . . 1.405(7) no
C2 C3 . . 1.356(8) no
C2 H2A . . 0.9300 no
C3 C4 . . 1.399(8) no
C3 H3A . . 0.9300 no
C4 C9 . . 1.404(7) no
C4 C5 . . 1.415(8) no
C5 C6 . . 1.359(9) no
C5 H5A . . 0.9300 no
C6 C7 . . 1.399(10) no
C6 H6A . . 0.9300 no
C7 C8 . . 1.372(8) no
C7 H7A . . 0.9300 no
C8 C9 . . 1.406(8) no
C8 H8A . . 0.9300 no
C9 N1 . . 1.369(6) no
N1 H1C . . 0.8994 no
O2 Sm1 . 5_566 2.330(4) no
O3 Sm1 . 3_456 2.310(3) no
O5 Sm1 . 5_666 2.527(3) no
O1W H1WA . . 0.9001 no
O1W H1WB . . 0.9000 no
O2W H2WA . . 0.9001 no
O2W H2WB . . 0.9000 no
Sm1 Sm1 . 5_666 4.2271(5) no
Sm1 Sm1 . 7 5.9849(6) no
Sm1 Sm1 . 3_456 6.3125(5) no
Sm1 Sm1 . 5_566 4.7532(5) no

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O3 Sm1 O2 3_556 . 5_566 143.51(13) no
O3 Sm1 O1 3_556 . . 83.76(12) no
O2 Sm1 O1 5_566 . . 113.26(13) no
O3 Sm1 O1W 3_556 . . 77.63(12) no
O2 Sm1 O1W 5_566 . . 74.52(13) no
O1 Sm1 O1W . . . 79.38(12) no
O3 Sm1 O4 3_556 . . 74.12(12) no
O2 Sm1 O4 5_566 . . 74.79(12) no
O1 Sm1 O4 . . . 145.97(12) no
O1W Sm1 O4 . . . 70.93(12) no
O3 Sm1 O5 3_556 . . 85.33(11) no
O2 Sm1 O5 5_566 . . 92.53(13) no
O1 Sm1 O5 . . . 148.79(11) no
O1W Sm1 O5 . . . 126.38(12) no
O4 Sm1 O5 . . . 55.50(11) no
O3 Sm1 O5 3_556 . 5_666 77.20(11) no
O2 Sm1 O5 5_566 . 5_666 134.60(12) no
O1 Sm1 O5 . . 5_666 82.79(11) no
O1W Sm1 O5 . . 5_666 150.48(11) no
O4 Sm1 O5 . . 5_666 115.99(11) no
O5 Sm1 O5 . . 5_666 66.28(12) no
O3 Sm1 O2W 3_556 . . 146.60(12) no
O2 Sm1 O2W 5_566 . . 69.17(12) no
O1 Sm1 O2W . . . 86.61(12) no
O1W Sm1 O2W . . . 131.64(11) no
O4 Sm1 O2W . . . 125.65(12) no
O5 Sm1 O2W . . . 86.61(11) no
O5 Sm1 O2W 5_666 . . 69.88(10) no
O3 Sm1 S1 3_556 . . 79.33(9) no
O2 Sm1 S1 5_566 . . 81.88(10) no
O1 Sm1 S1 . . . 163.02(9) no
O1W Sm1 S1 . . . 98.37(9) no
O4 Sm1 S1 . . . 27.44(8) no
O5 Sm1 S1 . . . 28.10(8) no
O5 Sm1 S1 5_666 . . 91.89(8) no
O2W Sm1 S1 . . . 106.76(9) no
O3 Sm1 P1 3_556 . . 100.00(9) no
O2 Sm1 P1 5_566 . . 90.08(11) no
O1 Sm1 P1 . . . 23.76(8) no
O1W Sm1 P1 . . . 66.49(9) no
O4 Sm1 P1 . . . 137.24(8) no
O5 Sm1 P1 . . . 167.07(8) no
O5 Sm1 P1 5_666 . . 103.20(8) no
O2W Sm1 P1 . . . 82.50(9) no
S1 Sm1 P1 . . . 164.41(3) no
O3 P1 O2 . . . 116.4(2) no
O3 P1 O1 . . . 114.3(2) no
O2 P1 O1 . . . 110.3(2) no
O3 P1 C1 . . . 103.6(2) no
O2 P1 C1 . . . 105.7(2) no
O1 P1 C1 . . . 105.3(2) no
O3 P1 Sm1 . . . 123.79(14) no
O2 P1 Sm1 . . . 73.00(17) no
O1 P1 Sm1 . . . 39.29(13) no
C1 P1 Sm1 . . . 128.15(15) no
O6 S1 O7 . . . 112.0(2) no
O6 S1 O4 . . . 110.8(2) no
O7 S1 O4 . . . 109.7(2) no
O6 S1 O5 . . . 110.3(2) no
O7 S1 O5 . . . 110.4(2) no
O4 S1 O5 . . . 103.33(19) no
O6 S1 Sm1 . . . 122.13(16) no
O7 S1 Sm1 . . . 125.89(15) no
O4 S1 Sm1 . . . 51.17(13) no
O5 S1 Sm1 . . . 52.23(13) no
N1 C1 C2 . . . 118.7(4) no
N1 C1 P1 . . . 117.9(3) no
C2 C1 P1 . . . 123.4(4) no
C3 C2 C1 . . . 119.7(5) no
C3 C2 H2A . . . 120.20 no
C1 C2 H2A . . . 120.20 no
C2 C3 C4 . . . 121.2(5) no
C2 C3 H3A . . . 119.40 no
C4 C3 H3A . . . 119.40 no
C3 C4 C9 . . . 118.1(5) no
C3 C4 C5 . . . 123.7(5) no
C9 C4 C5 . . . 118.2(5) no
C6 C5 C4 . . . 120.5(6) no
C6 C5 H5A . . . 119.80 no
C4 C5 H5A . . . 119.80 no
C5 C6 C7 . . . 120.3(6) no
C5 C6 H6A . . . 119.90 no
C7 C6 H6A . . . 119.90 no
C8 C7 C6 . . . 121.6(6) no
C8 C7 H7A . . . 119.20 no
C6 C7 H7A . . . 119.20 no
C7 C8 C9 . . . 118.2(6) no
C7 C8 H8A . . . 120.90 no
C9 C8 H8A . . . 120.90 no
N1 C9 C4 . . . 118.2(5) no
N1 C9 C8 . . . 120.6(5) no
C4 C9 C8 . . . 121.2(5) no
C1 N1 C9 . . . 124.2(4) no
C1 N1 H1C . . . 119.60 no
C9 N1 H1C . . . 116.20 no
P1 O1 Sm1 . . . 116.96(19) no
P1 O2 Sm1 . . 5_566 162.0(3) no
P1 O3 Sm1 . . 3_456 174.6(2) no
S1 O4 Sm1 . . . 101.39(17) no
S1 O5 Sm1 . . . 99.67(17) no
S1 O5 Sm1 . . 5_666 138.1(2) no
Sm1 O5 Sm1 . . 5_666 113.72(12) no
Sm1 O1W H1WA . . . 125.50 no
Sm1 O1W H1WB . . . 117.00 no
H1WA O1W H1WB . . . 117.40 no
Sm1 O2W H2WA . . . 111.20 no
Sm1 O2W H2WB . . . 106.50 no
H2WA O2W H2WB . . . 117.90 no

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O3 P1 C1 N1 . . . . 3.0(4) no
O2 P1 C1 N1 . . . . 125.9(4) no
O1 P1 C1 N1 . . . . -117.4(4) no
Sm1 P1 C1 N1 . . . . -153.7(3) no
O3 P1 C1 C2 . . . . -175.9(4) no
O2 P1 C1 C2 . . . . -53.0(5) no
O1 P1 C1 C2 . . . . 63.8(5) no
Sm1 P1 C1 C2 . . . . 27.5(5) no
N1 C1 C2 C3 . . . . 1.5(8) no
P1 C1 C2 C3 . . . . -179.6(4) no
C1 C2 C3 C4 . . . . -1.7(9) no
C2 C3 C4 C9 . . . . 0.6(9) no
C2 C3 C4 C5 . . . . 179.7(6) no
C3 C4 C5 C6 . . . . 179.4(6) no
C9 C4 C5 C6 . . . . -1.5(9) no
C4 C5 C6 C7 . . . . -0.1(10) no
C5 C6 C7 C8 . . . . 1.2(10) no
C6 C7 C8 C9 . . . . -0.6(9) no
C3 C4 C9 N1 . . . . 0.8(8) no
C5 C4 C9 N1 . . . . -178.4(5) no
C3 C4 C9 C8 . . . . -178.8(5) no
C5 C4 C9 C8 . . . . 2.1(8) no
C7 C8 C9 N1 . . . . 179.4(5) no
C7 C8 C9 C4 . . . . -1.0(9) no
C2 C1 N1 C9 . . . . -0.2(7) no
P1 C1 N1 C9 . . . . -179.0(4) no
C4 C9 N1 C1 . . . . -1.0(7) no
C8 C9 N1 C1 . . . . 178.5(5) no
O3 P1 O1 Sm1 . . . . 114.3(2) no
O2 P1 O1 Sm1 . . . . -19.1(3) no
C1 P1 O1 Sm1 . . . . -132.7(2) no
O3 P1 O2 Sm1 . . . 5_566 39.2(8) no
O1 P1 O2 Sm1 . . . 5_566 171.5(7) no
C1 P1 O2 Sm1 . . . 5_566 -75.2(8) no
Sm1 P1 O2 Sm1 . . . 5_566 159.0(8) no
O6 S1 O4 Sm1 . . . . -115.11(19) no
O7 S1 O4 Sm1 . . . . 120.77(18) no
O5 S1 O4 Sm1 . . . . 3.1(2) no
O6 S1 O5 Sm1 . . . . 115.5(2) no
O7 S1 O5 Sm1 . . . . -120.21(18) no
O4 S1 O5 Sm1 . . . . -3.0(2) no
O6 S1 O5 Sm1 . . . 5_666 -101.3(3) no
O7 S1 O5 Sm1 . . . 5_666 23.0(3) no
O4 S1 O5 Sm1 . . . 5_666 140.2(3) no
Sm1 S1 O5 Sm1 . . . 5_666 143.2(3) no
Sm1 O1 O3 Sm1 . . . 3_456 -86.83(39) no
Sm1 O1 O2 Sm1 . . . 5_566 8.38(68) no
Sm1 O2 O3 Sm1 5_566 . . 3_456 -14.97(45) no

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1C O4 . . 3_456 0.9000 1.9500 2.817(5) 161.80 no
O1W H1WA O6 . . 7_545 0.9000 1.8100 2.678(5) 161.00 no
O1W H1WB O2W . . 5_566 0.9000 1.8900 2.748(5) 158.20 no
O2W H2WA O1 . . 7 0.9000 1.9600 2.797(5) 155.00 no
O2W H2WB O7 . . 5_666 0.9000 1.7500 2.642(5) 169.10 no
####################################################################### 
# 
# 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_51011Bm
_database_code_depnum_ccdc_archive 'CCDC 2233021'
loop_
_audit_author_name
_audit_author_address
Nd
;NanJing university
China
;
_audit_update_record             
;
2022-12-27 deposited with the CCDC.	2023-07-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H11 N Nd O9 P S'
_chemical_formula_sum            'C9 H11 N Nd O9 P S'
_chemical_formula_weight         484.46

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'
Nd Nd -0.1943 3.0179 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-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                   8.4677(19)
_cell_length_b                   12.060(3)
_cell_length_c                   26.514(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2707.5(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    805
_cell_measurement_theta_min      3.04
_cell_measurement_theta_max      27.8

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.377
_exptl_crystal_F_000             1880
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    4.156
_shelx_estimated_absorpt_T_min   0.435
_shelx_estimated_absorpt_T_max   0.490
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.385
_exptl_absorpt_correction_T_max  0.490
_exptl_absorpt_process_details   'SADABS(Bruker, 2000)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13512
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.854
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2667
_reflns_number_gt                2517
_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)+(0.0587P)²+23.3086P] 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         2667
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0420
_refine_ls_wR_factor_ref         0.1112
_refine_ls_wR_factor_gt          0.1085
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.003
_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
Nd1 Nd 0.26196(4) 0.44341(3) 0.48820(2) 0.01529(14) Uani 1 1 d . . . . .
P1 P -0.01146(18) 0.31332(12) 0.55651(6) 0.0145(3) Uani 1 1 d . . . . .
S1 S 0.45998(19) 0.55124(12) 0.39921(6) 0.0179(3) Uani 1 1 d . . . . .
C1 C -0.0418(7) 0.3167(5) 0.6247(2) 0.0185(13) Uani 1 1 d . . . . .
C2 C 0.0065(9) 0.4056(6) 0.6553(3) 0.0283(15) Uani 1 1 d . . . . .
H2A H 0.0543 0.4676 0.6411 0.034 Uiso 1 1 calc R U . . .
C3 C -0.0177(9) 0.4000(7) 0.7059(3) 0.0331(17) Uani 1 1 d . . . . .
H3A H 0.0167 0.4580 0.7261 0.040 Uiso 1 1 calc R U . . .
C4 C -0.0929(8) 0.3091(6) 0.7283(2) 0.0258(15) Uani 1 1 d . . . . .
C5 C -0.1209(10) 0.2996(7) 0.7806(3) 0.0376(19) Uani 1 1 d . . . . .
H5A H -0.0890 0.3558 0.8023 0.045 Uiso 1 1 calc R U . . .
C6 C -0.1949(11) 0.2080(7) 0.7990(3) 0.043(2) Uani 1 1 d . . . . .
H6A H -0.2107 0.2015 0.8336 0.052 Uiso 1 1 calc R U . . .
C7 C -0.2468(10) 0.1246(8) 0.7675(3) 0.040(2) Uani 1 1 d . . . . .
H7A H -0.2999 0.0640 0.7811 0.048 Uiso 1 1 calc R U . . .
C8 C -0.2210(9) 0.1297(7) 0.7161(3) 0.0328(17) Uani 1 1 d . . . . .
H8A H -0.2549 0.0730 0.6950 0.039 Uiso 1 1 calc R U . . .
C9 C -0.1431(8) 0.2220(6) 0.6968(2) 0.0239(14) Uani 1 1 d . . . . .
N1 N -0.1115(6) 0.2313(4) 0.64624(18) 0.0174(11) Uani 1 1 d . . . . .
H1C H -0.1413 0.1728 0.6272 0.021 Uiso 1 1 d R U . . .
O1 O 0.1660(5) 0.3096(4) 0.54906(17) 0.0230(10) Uani 1 1 d . . . . .
O2 O -0.0734(7) 0.4207(4) 0.53667(18) 0.0320(12) Uani 1 1 d . . . . .
O3 O -0.0964(5) 0.2114(4) 0.54042(16) 0.0232(10) Uani 1 1 d . . . . .
O4 O 0.3192(6) 0.4790(4) 0.39628(17) 0.0236(10) Uani 1 1 d . . . . .
O5 O 0.4946(5) 0.5575(3) 0.45467(16) 0.0203(10) Uani 1 1 d . . . . .
O6 O 0.4244(6) 0.6608(4) 0.37972(17) 0.0282(11) Uani 1 1 d . . . . .
O7 O 0.5911(6) 0.5000(4) 0.37222(17) 0.0283(11) Uani 1 1 d . . . . .
O1W O 0.0722(5) 0.3447(4) 0.43651(18) 0.0276(11) Uani 1 1 d . . . . .
H1WA H 0.0903 0.2786 0.4214 0.033 Uiso 1 1 d R U . . .
H1WB H -0.0251 0.3747 0.4342 0.033 Uiso 1 1 d R U . . .
O2W O 0.2372(5) 0.5933(4) 0.55557(19) 0.0245(10) Uani 1 1 d . . . . .
H2WA H 0.2648 0.6630 0.5463 0.029 Uiso 1 1 d R U . . .
H2WB H 0.2915 0.5618 0.5810 0.029 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
Nd1 O3 2.346(4) 4_556 ?
Nd1 O2 2.381(5) 5_566 ?
Nd1 O1 2.422(4) . ?
Nd1 O1W 2.424(5) . ?
Nd1 O4 2.522(5) . ?
Nd1 O2W 2.550(5) . ?
Nd1 O5 2.558(5) 5_666 ?
Nd1 O5 2.562(4) . ?
Nd1 S1 3.1735(16) . ?
Nd1 P1 3.3319(16) . ?
P1 O3 1.486(5) . ?
P1 O2 1.493(5) . ?
P1 O1 1.516(5) . ?
P1 C1 1.827(6) . ?
S1 O6 1.450(5) . ?
S1 O7 1.458(5) . ?
S1 O4 1.479(5) . ?
S1 O5 1.501(5) . ?
C1 N1 1.317(8) . ?
C1 C2 1.405(9) . ?
C2 C3 1.357(10) . ?
C2 H2A 0.9300 . ?
C3 C4 1.400(10) . ?
C3 H3A 0.9300 . ?
C4 C9 1.407(10) . ?
C4 C5 1.412(10) . ?
C5 C6 1.361(12) . ?
C5 H5A 0.9300 . ?
C6 C7 1.379(13) . ?
C6 H6A 0.9300 . ?
C7 C8 1.382(11) . ?
C7 H7A 0.9300 . ?
C8 C9 1.392(10) . ?
C8 H8A 0.9300 . ?
C9 N1 1.371(8) . ?
N1 H1C 0.9033 . ?
O2 Nd1 2.381(5) 5_566 ?
O3 Nd1 2.346(4) 4_456 ?
O5 Nd1 2.558(5) 5_666 ?
O1W H1WA 0.9056 . ?
O1W H1WB 0.9019 . ?
O2W H2WA 0.9065 . ?
O2W H2WB 0.9000 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 Nd1 O2 143.25(16) 4_556 5_566 ?
O3 Nd1 O1 81.77(16) 4_556 . ?
O2 Nd1 O1 114.71(17) 5_566 . ?
O3 Nd1 O1W 76.43(16) 4_556 . ?
O2 Nd1 O1W 74.74(17) 5_566 . ?
O1 Nd1 O1W 80.05(16) . . ?
O3 Nd1 O4 74.01(15) 4_556 . ?
O2 Nd1 O4 75.18(16) 5_566 . ?
O1 Nd1 O4 145.25(15) . . ?
O1W Nd1 O4 70.39(15) . . ?
O3 Nd1 O2W 146.41(15) 4_556 . ?
O2 Nd1 O2W 69.57(16) 5_566 . ?
O1 Nd1 O2W 88.74(16) . . ?
O1W Nd1 O2W 133.59(15) . . ?
O4 Nd1 O2W 124.90(16) . . ?
O3 Nd1 O5 77.06(15) 4_556 5_666 ?
O2 Nd1 O5 135.01(16) 5_566 5_666 ?
O1 Nd1 O5 82.72(14) . 5_666 ?
O1W Nd1 O5 150.10(15) . 5_666 ?
O4 Nd1 O5 114.71(15) . 5_666 ?
O2W Nd1 O5 69.79(14) . 5_666 ?
O3 Nd1 O5 85.52(15) 4_556 . ?
O2 Nd1 O5 92.86(17) 5_566 . ?
O1 Nd1 O5 147.87(15) . . ?
O1W Nd1 O5 125.24(15) . . ?
O4 Nd1 O5 54.93(14) . . ?
O2W Nd1 O5 85.74(15) . . ?
O5 Nd1 O5 65.67(16) 5_666 . ?
O3 Nd1 S1 79.36(12) 4_556 . ?
O2 Nd1 S1 82.32(13) 5_566 . ?
O1 Nd1 S1 161.00(11) . . ?
O1W Nd1 S1 97.53(12) . . ?
O4 Nd1 S1 27.14(11) . . ?
O2W Nd1 S1 105.89(12) . . ?
O5 Nd1 S1 90.92(10) 5_666 . ?
O5 Nd1 S1 27.82(10) . . ?
O3 Nd1 P1 99.00(12) 4_556 . ?
O2 Nd1 P1 90.49(14) 5_566 . ?
O1 Nd1 P1 24.66(11) . . ?
O1W Nd1 P1 67.40(12) . . ?
O4 Nd1 P1 137.65(11) . . ?
O2W Nd1 P1 84.02(12) . . ?
O5 Nd1 P1 103.66(10) 5_666 . ?
O5 Nd1 P1 167.36(10) . . ?
S1 Nd1 P1 164.64(4) . . ?
O3 P1 O2 116.5(3) . . ?
O3 P1 O1 114.7(3) . . ?
O2 P1 O1 109.1(3) . . ?
O3 P1 C1 103.6(3) . . ?
O2 P1 C1 106.3(3) . . ?
O1 P1 C1 105.6(3) . . ?
O3 P1 Nd1 124.71(19) . . ?
O2 P1 Nd1 69.1(2) . . ?
O1 P1 Nd1 41.80(18) . . ?
C1 P1 Nd1 128.7(2) . . ?
O6 S1 O7 111.7(3) . . ?
O6 S1 O4 110.5(3) . . ?
O7 S1 O4 109.8(3) . . ?
O6 S1 O5 110.1(3) . . ?
O7 S1 O5 110.7(3) . . ?
O4 S1 O5 103.8(3) . . ?
O6 S1 Nd1 121.9(2) . . ?
O7 S1 Nd1 126.4(2) . . ?
O4 S1 Nd1 51.06(18) . . ?
O5 S1 Nd1 52.79(18) . . ?
N1 C1 C2 118.5(6) . . ?
N1 C1 P1 118.3(5) . . ?
C2 C1 P1 123.2(5) . . ?
C3 C2 C1 119.2(7) . . ?
C3 C2 H2A 120.4 . . ?
C1 C2 H2A 120.4 . . ?
C2 C3 C4 121.8(7) . . ?
C2 C3 H3A 119.1 . . ?
C4 C3 H3A 119.1 . . ?
C3 C4 C9 118.0(6) . . ?
C3 C4 C5 123.9(7) . . ?
C9 C4 C5 118.1(7) . . ?
C6 C5 C4 119.8(7) . . ?
C6 C5 H5A 120.1 . . ?
C4 C5 H5A 120.1 . . ?
C5 C6 C7 121.4(7) . . ?
C5 C6 H6A 119.3 . . ?
C7 C6 H6A 119.3 . . ?
C6 C7 C8 120.9(8) . . ?
C6 C7 H7A 119.5 . . ?
C8 C7 H7A 119.5 . . ?
C7 C8 C9 118.3(7) . . ?
C7 C8 H8A 120.8 . . ?
C9 C8 H8A 120.8 . . ?
N1 C9 C8 121.2(6) . . ?
N1 C9 C4 117.4(6) . . ?
C8 C9 C4 121.4(6) . . ?
C1 N1 C9 125.1(6) . . ?
C1 N1 H1C 119.6 . . ?
C9 N1 H1C 115.3 . . ?
P1 O1 Nd1 113.5(2) . . ?
P1 O2 Nd1 158.4(4) . 5_566 ?
P1 O3 Nd1 176.8(3) . 4_456 ?
S1 O4 Nd1 101.8(2) . . ?
S1 O5 Nd1 137.5(3) . 5_666 ?
S1 O5 Nd1 99.4(2) . . ?
Nd1 O5 Nd1 114.33(16) 5_666 . ?
Nd1 O1W H1WA 124.8 . . ?
Nd1 O1W H1WB 116.6 . . ?
H1WA O1W H1WB 118.5 . . ?
Nd1 O2W H2WA 116.4 . . ?
Nd1 O2W H2WB 100.5 . . ?
H2WA O2W H2WB 117.6 . . ?

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
O3 P1 C1 N1 6.5(6) . . . . ?
O2 P1 C1 N1 129.8(5) . . . . ?
O1 P1 C1 N1 -114.4(5) . . . . ?
Nd1 P1 C1 N1 -154.2(4) . . . . ?
O3 P1 C1 C2 -173.9(6) . . . . ?
O2 P1 C1 C2 -50.6(6) . . . . ?
O1 P1 C1 C2 65.2(6) . . . . ?
Nd1 P1 C1 C2 25.4(7) . . . . ?
N1 C1 C2 C3 1.1(10) . . . . ?
P1 C1 C2 C3 -178.5(6) . . . . ?
C1 C2 C3 C4 -1.6(12) . . . . ?
C2 C3 C4 C9 0.3(11) . . . . ?
C2 C3 C4 C5 -179.8(8) . . . . ?
C3 C4 C5 C6 -179.9(8) . . . . ?
C9 C4 C5 C6 0.0(11) . . . . ?
C4 C5 C6 C7 -1.5(13) . . . . ?
C5 C6 C7 C8 2.0(14) . . . . ?
C6 C7 C8 C9 -0.9(13) . . . . ?
C7 C8 C9 N1 178.9(7) . . . . ?
C7 C8 C9 C4 -0.7(11) . . . . ?
C3 C4 C9 N1 1.4(10) . . . . ?
C5 C4 C9 N1 -178.4(6) . . . . ?
C3 C4 C9 C8 -179.0(7) . . . . ?
C5 C4 C9 C8 1.2(10) . . . . ?
C2 C1 N1 C9 0.7(9) . . . . ?
P1 C1 N1 C9 -179.6(5) . . . . ?
C8 C9 N1 C1 178.4(6) . . . . ?
C4 C9 N1 C1 -2.0(9) . . . . ?
O3 P1 O1 Nd1 115.2(3) . . . . ?
O2 P1 O1 Nd1 -17.5(3) . . . . ?
C1 P1 O1 Nd1 -131.4(3) . . . . ?
O3 P1 O2 Nd1 40.6(9) . . . 5_566 ?
O1 P1 O2 Nd1 172.4(7) . . . 5_566 ?
C1 P1 O2 Nd1 -74.2(8) . . . 5_566 ?
Nd1 P1 O2 Nd1 160.0(8) . . . 5_566 ?
O6 S1 O4 Nd1 -115.0(3) . . . . ?
O7 S1 O4 Nd1 121.4(2) . . . . ?
O5 S1 O4 Nd1 3.0(3) . . . . ?
O6 S1 O5 Nd1 -101.7(4) . . . 5_666 ?
O7 S1 O5 Nd1 22.3(4) . . . 5_666 ?
O4 S1 O5 Nd1 140.0(3) . . . 5_666 ?
Nd1 S1 O5 Nd1 142.9(4) . . . 5_666 ?
O6 S1 O5 Nd1 115.4(3) . . . . ?
O7 S1 O5 Nd1 -120.7(3) . . . . ?
O4 S1 O5 Nd1 -2.9(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1C O4 0.90 1.96 2.837(7) 162.5 4_456
O1W H1WA O6 0.91 1.80 2.681(7) 162.4 8_655
O1W H1WB O2W 0.90 1.86 2.732(6) 163.1 5_566
O2W H2WA O1 0.91 1.86 2.740(7) 161.7 8_665
O2W H2WB O7 0.90 1.76 2.654(7) 176.1 5_666

_refine_diff_density_max         0.804
_refine_diff_density_min         -0.849
_refine_diff_density_rms         0.136

_shelxl_version_number           2013-4

