# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_N2S2POK
_database_code_depnum_ccdc_archive 'CCDC 1969818'
loop_
_audit_author_name
_audit_author_address
'Briana Schrage'
;The University of Akron
United States of America
;
_audit_update_record             
;
2019-12-03 deposited with the CCDC.	2020-02-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H25 K N O9 P S'
_chemical_formula_weight         357.40

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'
K K 0.2009 0.2494 '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'

_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                   18.4319(11)
_cell_length_b                   8.4812(5)
_cell_length_c                   10.0288(5)
_cell_angle_alpha                90
_cell_angle_beta                 100.191(4)
_cell_angle_gamma                90
_cell_volume                     1543.01(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5170
_cell_measurement_theta_min      3.24
_cell_measurement_theta_max      28.30

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_F_000             760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.193
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.619
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6754
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14493
_diffrn_reflns_av_unetI/netI     0.0745
_diffrn_reflns_av_R_equivalents  0.0642
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.245
_diffrn_reflns_theta_max         28.413
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3854
_reflns_number_gt                2745
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker 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)+(0.0329P)²+1.0736P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3854
_refine_ls_number_parameters     224
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0743
_refine_ls_R_factor_gt           0.0452
_refine_ls_wR_factor_ref         0.1008
_refine_ls_wR_factor_gt          0.0880
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_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
C1 C 0.92414(13) 0.6920(3) 1.1353(2) 0.0113(5) Uani 1 1 d . . . . .
H1A H 0.951387 0.607901 1.191622 0.014 Uiso 1 1 calc R U . . .
H1B H 0.882165 0.723890 1.178642 0.014 Uiso 1 1 calc R U . . .
C2 C 0.89411(13) 0.6249(3) 0.9958(2) 0.0119(5) Uani 1 1 d . . . . .
H2A H 0.935221 0.590371 0.951230 0.014 Uiso 1 1 calc R U . . .
H2B H 0.865478 0.706412 0.938456 0.014 Uiso 1 1 calc R U . . .
C3 C 0.84478(13) 0.4852(3) 1.0135(2) 0.0107(5) Uani 1 1 d . . . . .
H3A H 0.870399 0.419066 1.088676 0.013 Uiso 1 1 calc R U . . .
H3B H 0.799208 0.525760 1.040818 0.013 Uiso 1 1 calc R U . . .
C4 C 0.76748(13) 0.4626(3) 0.7857(2) 0.0111(5) Uani 1 1 d . . . . .
H4A H 0.789732 0.561122 0.758637 0.013 Uiso 1 1 calc R U . . .
H4B H 0.725168 0.492852 0.828802 0.013 Uiso 1 1 calc R U . . .
C5 C 0.88767(12) 0.3191(3) 0.8332(2) 0.0112(5) Uani 1 1 d . . . . .
H5A H 0.914955 0.408345 0.801886 0.013 Uiso 1 1 calc R U . . .
H5B H 0.869252 0.251765 0.753743 0.013 Uiso 1 1 calc R U . . .
C6 C 0.94005(13) 0.2233(3) 0.9371(2) 0.0124(5) Uani 1 1 d . . . . .
H6A H 0.912250 0.137016 0.971572 0.015 Uiso 1 1 calc R U . . .
H6B H 0.960259 0.291997 1.014659 0.015 Uiso 1 1 calc R U . . .
H7 H 0.4823(19) 0.322(4) 0.480(4) 0.042(10) Uiso 1 1 d . . . . .
H8 H 0.552(3) 0.320(6) 0.568(4) 0.083(16) Uiso 1 1 d . . . . .
H9 H 0.3694(17) 0.681(4) 0.726(3) 0.025(9) Uiso 1 1 d . . . . .
H10 H 0.3812(17) 0.646(4) 0.611(3) 0.026(9) Uiso 1 1 d . . . . .
H11 H 0.6126(17) 0.699(4) 0.766(3) 0.031(9) Uiso 1 1 d . . . . .
H12 H 0.614(2) 0.585(5) 0.659(4) 0.054(12) Uiso 1 1 d . . . . .
H13 H 0.6477(19) 0.459(4) 1.067(3) 0.034(10) Uiso 1 1 d . . . . .
H14 H 0.633(2) 0.591(5) 1.005(4) 0.044(13) Uiso 1 1 d . . . . .
H15 H 0.7172(19) 0.819(4) 0.884(3) 0.040(10) Uiso 1 1 d . . . . .
H16 H 0.674(2) 0.857(5) 0.963(4) 0.053(14) Uiso 1 1 d . . . . .
H17 H 0.7721(19) 0.999(5) 0.774(3) 0.036(11) Uiso 1 1 d . . . . .
H18 H 0.7965(18) 0.994(4) 0.901(4) 0.041(11) Uiso 1 1 d . . . . .
H19 H 0.8017(16) 0.301(4) 0.925(3) 0.022(8) Uiso 1 1 d . . . . .
K1 K 0.49840(3) 0.44453(8) 0.81882(5) 0.01562(15) Uani 1 1 d . . . . .
N1 N 0.82330(11) 0.3819(3) 0.89004(19) 0.0090(4) Uani 1 1 d . . . . .
O1 O 0.66132(9) 0.4389(2) 0.57383(16) 0.0127(4) Uani 1 1 d . . . . .
O2 O 0.71864(9) 0.1830(2) 0.67580(16) 0.0133(4) Uani 1 1 d . . . . .
O3 O 0.78911(9) 0.3580(2) 0.53915(16) 0.0118(4) Uani 1 1 d . . . . .
O4 O 0.50603(12) 0.2994(3) 0.5637(2) 0.0233(5) Uani 1 1 d . . . . .
O5 O 0.40166(10) 0.6744(3) 0.6827(2) 0.0178(5) Uani 1 1 d . . . . .
O6 O 0.58524(10) 0.6496(3) 0.69839(19) 0.0169(4) Uani 1 1 d . . . . .
O7 O 0.61400(11) 0.5169(3) 1.0251(2) 0.0178(5) Uani 1 1 d . . . . .
O8 O 0.68092(12) 0.7879(3) 0.9212(2) 0.0234(5) Uani 1 1 d . . . . .
O9 O 0.79530(11) 0.9430(3) 0.8257(2) 0.0172(4) Uani 1 1 d . . . . .
P1 P 0.73167(3) 0.34967(8) 0.63061(6) 0.00870(15) Uani 1 1 d . . . . .
S1 S 0.98469(3) 0.85982(8) 1.13336(6) 0.01363(16) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.520(3) . ?
C1 S1 1.811(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.522(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 N1 1.511(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 N1 1.497(3) . ?
C4 P1 1.846(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 N1 1.502(3) . ?
C5 C6 1.524(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 S1 1.808(2) 3_767 ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
K1 O7 2.763(2) . ?
K1 O6 2.780(2) . ?
K1 O5 2.826(2) . ?
K1 O7 2.828(2) 3_667 ?
K1 O4 2.865(2) . ?
K1 O6 2.927(2) 2_646 ?
K1 O5 2.941(2) 2_646 ?
K1 O4 3.195(2) 4_566 ?
K1 O4 3.238(2) 2_656 ?
K1 K1 3.7442(11) 3_667 ?
K1 K1 4.4632(4) 2_646 ?
K1 K1 4.4632(4) 2_656 ?
K1 H8 3.05(4) . ?
N1 H19 0.89(3) . ?
O1 P1 1.5219(17) . ?
O2 P1 1.516(2) . ?
O3 P1 1.5202(17) . ?
O4 H7 0.90(4) . ?
O4 H8 0.85(5) . ?
O5 H9 0.80(3) . ?
O5 H10 0.79(3) . ?
O6 H11 0.88(3) . ?
O6 H12 0.90(4) . ?
O7 H13 0.84(4) . ?
O7 H14 0.77(4) . ?
O8 H15 0.87(4) . ?
O8 H16 0.75(4) . ?
O9 H17 0.77(4) . ?
O9 H18 0.87(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 S1 114.16(17) . . ?
C2 C1 H1A 108.7 . . ?
S1 C1 H1A 108.7 . . ?
C2 C1 H1B 108.7 . . ?
S1 C1 H1B 108.7 . . ?
H1A C1 H1B 107.6 . . ?
C1 C2 C3 108.17(19) . . ?
C1 C2 H2A 110.1 . . ?
C3 C2 H2A 110.1 . . ?
C1 C2 H2B 110.1 . . ?
C3 C2 H2B 110.1 . . ?
H2A C2 H2B 108.4 . . ?
N1 C3 C2 115.52(19) . . ?
N1 C3 H3A 108.4 . . ?
C2 C3 H3A 108.4 . . ?
N1 C3 H3B 108.4 . . ?
C2 C3 H3B 108.4 . . ?
H3A C3 H3B 107.5 . . ?
N1 C4 P1 116.81(18) . . ?
N1 C4 H4A 108.1 . . ?
P1 C4 H4A 108.1 . . ?
N1 C4 H4B 108.1 . . ?
P1 C4 H4B 108.1 . . ?
H4A C4 H4B 107.3 . . ?
N1 C5 C6 112.12(19) . . ?
N1 C5 H5A 109.2 . . ?
C6 C5 H5A 109.2 . . ?
N1 C5 H5B 109.2 . . ?
C6 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
C5 C6 S1 112.17(16) . 3_767 ?
C5 C6 H6A 109.2 . . ?
S1 C6 H6A 109.2 3_767 . ?
C5 C6 H6B 109.2 . . ?
S1 C6 H6B 109.2 3_767 . ?
H6A C6 H6B 107.9 . . ?
O7 K1 O6 76.08(6) . . ?
O7 K1 O5 123.06(7) . . ?
O6 K1 O5 73.80(6) . . ?
O7 K1 O7 95.93(6) . 3_667 ?
O6 K1 O7 134.62(7) . 3_667 ?
O5 K1 O7 74.10(6) . 3_667 ?
O7 K1 O4 127.64(6) . . ?
O6 K1 O4 75.99(6) . . ?
O5 K1 O4 89.52(6) . . ?
O7 K1 O4 134.47(6) 3_667 . ?
O7 K1 O6 124.21(7) . 2_646 ?
O6 K1 O6 147.85(4) . 2_646 ?
O5 K1 O6 106.28(6) . 2_646 ?
O7 K1 O6 72.65(6) 3_667 2_646 ?
O4 K1 O6 71.86(6) . 2_646 ?
O7 K1 O5 77.06(6) . 2_646 ?
O6 K1 O5 94.35(6) . 2_646 ?
O5 K1 O5 151.31(3) . 2_646 ?
O7 K1 O5 127.87(7) 3_667 2_646 ?
O4 K1 O5 62.03(6) . 2_646 ?
O6 K1 O5 70.00(6) 2_646 2_646 ?
O7 K1 O4 69.21(6) . 4_566 ?
O6 K1 O4 142.05(6) . 4_566 ?
O5 K1 O4 139.15(6) . 4_566 ?
O7 K1 O4 65.57(6) 3_667 4_566 ?
O4 K1 O4 113.94(2) . 4_566 ?
O6 K1 O4 56.17(6) 2_646 4_566 ?
O5 K1 O4 63.72(6) 2_646 4_566 ?
O7 K1 O4 65.61(6) . 2_656 ?
O6 K1 O4 68.30(6) . 2_656 ?
O5 K1 O4 58.67(6) . 2_656 ?
O7 K1 O4 67.84(6) 3_667 2_656 ?
O4 K1 O4 137.11(6) . 2_656 ?
O6 K1 O4 140.23(6) 2_646 2_656 ?
O5 K1 O4 141.43(6) 2_646 2_656 ?
O4 K1 O4 108.82(5) 4_566 2_656 ?
O7 K1 K1 48.70(4) . 3_667 ?
O6 K1 K1 110.67(5) . 3_667 ?
O5 K1 K1 101.29(5) . 3_667 ?
O7 K1 K1 47.23(4) 3_667 3_667 ?
O4 K1 K1 168.48(6) . 3_667 ?
O6 K1 K1 100.93(4) 2_646 3_667 ?
O5 K1 K1 107.36(4) 2_646 3_667 ?
O4 K1 K1 54.95(4) 4_566 3_667 ?
O4 K1 K1 53.87(4) 2_656 3_667 ?
O7 K1 K1 113.07(5) . 2_646 ?
O6 K1 K1 114.83(5) . 2_646 ?
O5 K1 K1 123.23(5) . 2_646 ?
O7 K1 K1 109.41(5) 3_667 2_646 ?
O4 K1 K1 46.38(5) . 2_646 ?
O6 K1 K1 37.40(4) 2_646 2_646 ?
O5 K1 K1 38.36(4) 2_646 2_646 ?
O4 K1 K1 67.75(4) 4_566 2_646 ?
O4 K1 K1 176.47(4) 2_656 2_646 ?
K1 K1 K1 122.69(3) 3_667 2_646 ?
O7 K1 K1 88.28(6) . 2_656 ?
O6 K1 K1 39.75(4) . 2_656 ?
O5 K1 K1 40.24(4) . 2_656 ?
O7 K1 K1 96.44(5) 3_667 2_656 ?
O4 K1 K1 97.28(5) . 2_656 ?
O6 K1 K1 146.02(4) 2_646 2_656 ?
O5 K1 K1 134.10(5) 2_646 2_656 ?
O4 K1 K1 148.40(5) 4_566 2_656 ?
O4 K1 K1 39.83(4) 2_656 2_656 ?
K1 K1 K1 93.59(2) 3_667 2_656 ?
K1 K1 K1 143.65(3) 2_646 2_656 ?
O7 K1 H8 112.1(9) . . ?
O6 K1 H8 64.2(9) . . ?
O5 K1 H8 96.3(9) . . ?
O7 K1 H8 150.7(9) 3_667 . ?
O4 K1 H8 16.2(9) . . ?
O6 K1 H8 84.1(9) 2_646 . ?
O5 K1 H8 55.3(9) 2_646 . ?
O4 K1 H8 115.6(9) 4_566 . ?
O4 K1 H8 131.0(9) 2_656 . ?
K1 K1 H8 159.4(9) 3_667 . ?
K1 K1 H8 52.5(9) 2_646 . ?
K1 K1 H8 92.9(9) 2_656 . ?
C4 N1 C5 112.84(18) . . ?
C4 N1 C3 110.9(2) . . ?
C5 N1 C3 114.00(18) . . ?
C4 N1 H19 109.1(18) . . ?
C5 N1 H19 108(2) . . ?
C3 N1 H19 100.9(19) . . ?
K1 O4 K1 164.19(9) . 4_565 ?
K1 O4 K1 93.79(6) . 2_646 ?
K1 O4 K1 71.18(5) 4_565 2_646 ?
K1 O4 H7 131(2) . . ?
K1 O4 H7 58(2) 4_565 . ?
K1 O4 H7 120(2) 2_646 . ?
K1 O4 H8 94(3) . . ?
K1 O4 H8 95(3) 4_565 . ?
K1 O4 H8 105(3) 2_646 . ?
H7 O4 H8 109(4) . . ?
K1 O5 K1 101.40(6) . 2_656 ?
K1 O5 H9 105(2) . . ?
K1 O5 H9 119(2) 2_656 . ?
K1 O5 H10 113(2) . . ?
K1 O5 H10 115(2) 2_656 . ?
H9 O5 H10 104(3) . . ?
K1 O6 K1 102.85(6) . 2_656 ?
K1 O6 H11 105(2) . . ?
K1 O6 H11 82(2) 2_656 . ?
K1 O6 H12 104(3) . . ?
K1 O6 H12 147(2) 2_656 . ?
H11 O6 H12 109(3) . . ?
K1 O7 K1 84.07(6) . 3_667 ?
K1 O7 H13 130(2) . . ?
K1 O7 H13 110(2) 3_667 . ?
K1 O7 H14 108(3) . . ?
K1 O7 H14 118(3) 3_667 . ?
H13 O7 H14 106(3) . . ?
H15 O8 H16 104(4) . . ?
H17 O9 H18 102(4) . . ?
O2 P1 O3 112.81(10) . . ?
O2 P1 O1 113.93(10) . . ?
O3 P1 O1 112.92(10) . . ?
O2 P1 C4 106.47(11) . . ?
O3 P1 C4 107.51(11) . . ?
O1 P1 C4 102.20(11) . . ?
C6 S1 C1 102.39(12) 3_767 . ?

_refine_diff_density_max         0.565
_refine_diff_density_min         -0.525
_refine_diff_density_rms         0.105

