# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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. 
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data_p21c
_database_code_depnum_ccdc_archive 'CCDC 1837294'
_audit_update_record             
;
2018-04-15 deposited with the CCDC.
2018-06-21 downloaded from the CCDC.
;
_audit_creation_date             2017-11-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C25 H47 N6 O2 P S'
_chemical_formula_sum            'C25 H47 N6 O2 P S'
_chemical_formula_weight         526.71
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   14.9831(2)
_cell_length_b                   9.7363(2)
_cell_length_c                   20.8595(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.8892(8)
_cell_angle_gamma                90
_cell_volume                     2954.01(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9943
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.276
_cell_measurement_theta_min      2.321
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.195
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1336 before and 0.0307 after correction.
The Ratio of minimum to maximum transmission is 0.7961.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.184
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1144
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            38731
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.297
_diffrn_reflns_theta_min         2.011
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6306
_reflns_number_total             7311
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     349
_refine_ls_number_reflns         7311
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0353
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0410P)²+1.4741P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0870
_refine_ls_wR_factor_ref         0.0912
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(S1A)=Sof(O1A)=1-FVAR(1)
 Sof(S1)=Sof(O1)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C6(H6), C9(H9), C17(H17), C20(H20), C23(H23)
3.b Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C10(H10A,
 H10B,H10C), C11(H11A,H11B,H11C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C),
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C21(H21A,H21B,H21C), C22(H22A,H22B,
 H22C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
S1 S 0.20405(4) 0.69663(6) 0.02803(2) 0.01865(15) Uani 0.912(3) 1 d . . P A 1
S1A S 0.2352(6) 0.7412(9) 0.0263(3) 0.0406(18) Uani 0.088(3) 1 d . . P A 2
P1 P 0.32664(2) 0.61392(3) 0.10112(2) 0.01511(8) Uani 1 1 d . . . . .
O1 O 0.22444(8) 0.84521(12) 0.02144(5) 0.0289(3) Uani 0.912(3) 1 d . . P A 1
O1A O 0.1490(8) 0.7147(18) 0.0526(6) 0.046(5) Uani 0.088(3) 1 d . . P A 2
O2 O 0.21552(8) 0.61632(11) -0.03056(4) 0.0322(2) Uani 1 1 d . . . . .
N1 N 0.36778(7) 0.70923(11) 0.16431(5) 0.0164(2) Uani 1 1 d . . . . .
N2 N 0.26898(7) 0.81465(11) 0.22552(5) 0.0168(2) Uani 1 1 d . . . . .
N3 N 0.34343(7) 0.63034(11) 0.26809(5) 0.0162(2) Uani 1 1 d . . . . .
N4 N 0.29228(7) 0.46633(11) 0.11987(5) 0.0166(2) Uani 1 1 d . . . . .
N5 N 0.14044(7) 0.38183(11) 0.11484(5) 0.0181(2) Uani 1 1 d . . . . .
N6 N 0.20815(7) 0.30471(11) 0.04017(5) 0.0169(2) Uani 1 1 d . . . . .
C1 C 0.32821(8) 0.71623(12) 0.21521(5) 0.0146(2) Uani 1 1 d . . . . .
C2 C 0.24636(9) 0.78960(14) 0.28596(6) 0.0196(2) Uani 1 1 d . . . . .
C3 C 0.29249(9) 0.67590(13) 0.31238(6) 0.0187(2) Uani 1 1 d . . . . .
C4 C 0.17876(11) 0.87250(17) 0.31175(7) 0.0315(3) Uani 1 1 d . . . . .
H4A H 0.1919 0.9704 0.3082 0.047 Uiso 1 1 calc GR . . . .
H4B H 0.1836 0.8490 0.3581 0.047 Uiso 1 1 calc GR . . . .
H4C H 0.1164 0.8525 0.2858 0.047 Uiso 1 1 calc GR . . . .
C5 C 0.28738(10) 0.60300(15) 0.37443(6) 0.0268(3) Uani 1 1 d . . . . .
H5A H 0.2528 0.5173 0.3633 0.040 Uiso 1 1 calc GR . . . .
H5B H 0.2563 0.6617 0.4005 0.040 Uiso 1 1 calc GR . . . .
H5C H 0.3497 0.5822 0.4002 0.040 Uiso 1 1 calc GR . . . .
C6 C 0.24133(9) 0.93080(13) 0.17966(6) 0.0201(2) Uani 1 1 d . . . . .
H6 H 0.2705 0.9153 0.1419 0.024 Uiso 1 1 calc R . . . .
C7 C 0.13803(10) 0.93407(16) 0.15074(7) 0.0302(3) Uani 1 1 d . . . . .
H7A H 0.1174 0.8439 0.1320 0.045 Uiso 1 1 calc GR . . . .
H7B H 0.1234 1.0039 0.1160 0.045 Uiso 1 1 calc GR . . . .
H7C H 0.1067 0.9565 0.1856 0.045 Uiso 1 1 calc GR . . . .
C8 C 0.27877(11) 1.06659(14) 0.21128(7) 0.0303(3) Uani 1 1 d . . . . .
H8A H 0.2462 1.0917 0.2451 0.045 Uiso 1 1 calc GR . . . .
H8B H 0.2696 1.1384 0.1774 0.045 Uiso 1 1 calc GR . . . .
H8C H 0.3446 1.0570 0.2317 0.045 Uiso 1 1 calc GR . . . .
C9 C 0.41514(9) 0.52322(13) 0.27813(6) 0.0198(2) Uani 1 1 d . . . . .
H9 H 0.4385 0.5214 0.2371 0.024 Uiso 1 1 calc R . . . .
C10 C 0.37837(10) 0.38028(14) 0.28581(7) 0.0269(3) Uani 1 1 d . . . . .
H10A H 0.3547 0.3770 0.3257 0.040 Uiso 1 1 calc GR . . . .
H10B H 0.4280 0.3130 0.2895 0.040 Uiso 1 1 calc GR . . . .
H10C H 0.3287 0.3586 0.2472 0.040 Uiso 1 1 calc GR . . . .
C11 C 0.49650(9) 0.56265(15) 0.33438(7) 0.0273(3) Uani 1 1 d . . . . .
H11A H 0.5193 0.6533 0.3256 0.041 Uiso 1 1 calc GR . . . .
H11B H 0.5456 0.4946 0.3378 0.041 Uiso 1 1 calc GR . . . .
H11C H 0.4769 0.5654 0.3759 0.041 Uiso 1 1 calc GR . . . .
C12 C 0.21826(8) 0.39337(12) 0.09194(5) 0.0157(2) Uani 1 1 d . . . . .
C13 C 0.08148(8) 0.28482(13) 0.07679(6) 0.0201(2) Uani 1 1 d . . . . .
C14 C 0.12329(8) 0.23763(13) 0.03063(6) 0.0193(2) Uani 1 1 d . . . . .
C15 C -0.00784(9) 0.24082(16) 0.08991(8) 0.0291(3) Uani 1 1 d . . . . .
H15A H 0.0031 0.2007 0.1342 0.044 Uiso 1 1 calc GR . . . .
H15B H -0.0368 0.1722 0.0571 0.044 Uiso 1 1 calc GR . . . .
H15C H -0.0485 0.3206 0.0871 0.044 Uiso 1 1 calc GR . . . .
C16 C 0.08891(10) 0.13334(14) -0.02206(7) 0.0260(3) Uani 1 1 d . . . . .
H16A H 0.0878 0.1735 -0.0653 0.039 Uiso 1 1 calc GR . . . .
H16B H 0.0267 0.1048 -0.0207 0.039 Uiso 1 1 calc GR . . . .
H16C H 0.1298 0.0533 -0.0147 0.039 Uiso 1 1 calc GR . . . .
C17 C 0.12156(9) 0.47386(14) 0.16599(7) 0.0236(3) Uani 1 1 d . . . . .
H17 H 0.1764 0.5351 0.1800 0.028 Uiso 1 1 calc R . . . .
C18 C 0.03953(10) 0.56689(15) 0.13857(8) 0.0319(3) Uani 1 1 d . . . . .
H18A H 0.0463 0.6089 0.0973 0.048 Uiso 1 1 calc GR . . . .
H18B H 0.0367 0.6391 0.1708 0.048 Uiso 1 1 calc GR . . . .
H18C H -0.0172 0.5126 0.1300 0.048 Uiso 1 1 calc GR . . . .
C19 C 0.11190(11) 0.39598(18) 0.22752(7) 0.0345(3) Uani 1 1 d . . . . .
H19A H 0.0553 0.3415 0.2171 0.052 Uiso 1 1 calc GR . . . .
H19B H 0.1094 0.4616 0.2627 0.052 Uiso 1 1 calc GR . . . .
H19C H 0.1648 0.3349 0.2423 0.052 Uiso 1 1 calc GR . . . .
C20 C 0.28245(9) 0.27959(13) 0.00634(6) 0.0213(3) Uani 1 1 d . . . . .
H20 H 0.3322 0.3474 0.0246 0.026 Uiso 1 1 calc R . . . .
C21 C 0.25268(12) 0.30539(16) -0.06784(7) 0.0337(3) Uani 1 1 d . . . . .
H21A H 0.2122 0.2309 -0.0890 0.051 Uiso 1 1 calc GR . . . .
H21B H 0.3071 0.3089 -0.0862 0.051 Uiso 1 1 calc GR . . . .
H21C H 0.2197 0.3930 -0.0761 0.051 Uiso 1 1 calc GR . . . .
C22 C 0.32388(9) 0.13780(15) 0.02295(7) 0.0268(3) Uani 1 1 d . . . . .
H22A H 0.3440 0.1276 0.0710 0.040 Uiso 1 1 calc GR . . . .
H22B H 0.3768 0.1266 0.0034 0.040 Uiso 1 1 calc GR . . . .
H22C H 0.2776 0.0677 0.0051 0.040 Uiso 1 1 calc GR . . . .
C23 C 0.41920(9) 0.60075(14) 0.05890(6) 0.0238(3) Uani 1 1 d . . . . .
H23 H 0.3942 0.5518 0.0162 0.029 Uiso 1 1 calc R . . . .
C24 C 0.45144(11) 0.74281(16) 0.04226(7) 0.0325(3) Uani 1 1 d . . . . .
H24A H 0.3982 0.7970 0.0193 0.049 Uiso 1 1 calc GR . . . .
H24B H 0.4944 0.7325 0.0138 0.049 Uiso 1 1 calc GR . . . .
H24C H 0.4823 0.7898 0.0831 0.049 Uiso 1 1 calc GR . . . .
C25 C 0.49794(10) 0.51406(17) 0.09901(8) 0.0335(3) Uani 1 1 d . . . . .
H25A H 0.5255 0.5610 0.1406 0.050 Uiso 1 1 calc GR . . . .
H25B H 0.5446 0.5012 0.0737 0.050 Uiso 1 1 calc GR . . . .
H25C H 0.4743 0.4244 0.1084 0.050 Uiso 1 1 calc GR . . . .


_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
S1 P1 2.2367(5) . ?
S1 O1 1.4916(13) . ?
S1 O2 1.4951(10) . ?
S1A P1 2.196(7) . ?
S1A O1A 1.541(15) . ?
S1A O2 1.675(7) . ?
P1 N1 1.6088(10) . ?
P1 N4 1.6062(11) . ?
P1 C23 1.8171(12) . ?
N1 C1 1.3362(14) . ?
N2 C1 1.3579(15) . ?
N2 C2 1.4031(14) . ?
N2 C6 1.4750(15) . ?
N3 C1 1.3591(15) . ?
N3 C3 1.4040(15) . ?
N3 C9 1.4757(16) . ?
N4 C12 1.3281(15) . ?
N5 C12 1.3667(15) . ?
N5 C13 1.4021(16) . ?
N5 C17 1.4717(16) . ?
N6 C12 1.3622(15) . ?
N6 C14 1.4005(15) . ?
N6 C20 1.4745(15) . ?
C2 C3 1.3506(18) . ?
C2 C4 1.4927(18) . ?
C3 C5 1.4943(17) . ?
C6 C7 1.5205(19) . ?
C6 C8 1.5231(18) . ?
C9 C10 1.5194(18) . ?
C9 C11 1.5244(18) . ?
C13 C14 1.3492(18) . ?
C13 C15 1.4916(17) . ?
C14 C16 1.4943(17) . ?
C17 C18 1.523(2) . ?
C17 C19 1.527(2) . ?
C20 C21 1.5248(18) . ?
C20 C22 1.5192(19) . ?
C23 C24 1.5321(19) . ?
C23 C25 1.527(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 P1 105.02(6) . . ?
O1 S1 O2 111.44(7) . . ?
O2 S1 P1 97.60(4) . . ?
O1A S1A P1 94.9(6) . . ?
O1A S1A O2 96.3(8) . . ?
O2 S1A P1 93.9(3) . . ?
N1 P1 S1 116.18(4) . . ?
N1 P1 S1A 107.9(2) . . ?
N1 P1 C23 104.54(6) . . ?
N4 P1 S1 103.26(4) . . ?
N4 P1 S1A 119.8(3) . . ?
N4 P1 N1 113.50(5) . . ?
N4 P1 C23 112.42(6) . . ?
C23 P1 S1 107.00(5) . . ?
C23 P1 S1A 96.6(2) . . ?
C1 N1 P1 121.64(8) . . ?
C1 N2 C2 109.13(10) . . ?
C1 N2 C6 122.06(10) . . ?
C2 N2 C6 128.70(10) . . ?
C1 N3 C3 109.14(10) . . ?
C1 N3 C9 121.64(10) . . ?
C3 N3 C9 128.47(10) . . ?
C12 N4 P1 130.88(9) . . ?
C12 N5 C13 109.39(10) . . ?
C12 N5 C17 122.14(10) . . ?
C13 N5 C17 128.01(10) . . ?
C12 N6 C14 109.42(10) . . ?
C12 N6 C20 122.10(10) . . ?
C14 N6 C20 128.22(10) . . ?
N1 C1 N2 126.40(11) . . ?
N1 C1 N3 126.40(11) . . ?
N2 C1 N3 107.12(10) . . ?
N2 C2 C4 124.12(11) . . ?
C3 C2 N2 107.38(10) . . ?
C3 C2 C4 128.41(11) . . ?
N3 C3 C5 124.67(11) . . ?
C2 C3 N3 107.24(10) . . ?
C2 C3 C5 127.96(11) . . ?
N2 C6 C7 111.96(11) . . ?
N2 C6 C8 111.57(10) . . ?
C7 C6 C8 112.81(12) . . ?
N3 C9 C10 113.10(11) . . ?
N3 C9 C11 110.59(10) . . ?
C10 C9 C11 113.12(11) . . ?
N4 C12 N5 125.68(11) . . ?
N4 C12 N6 127.51(11) . . ?
N6 C12 N5 106.45(10) . . ?
N5 C13 C15 124.10(12) . . ?
C14 C13 N5 107.22(11) . . ?
C14 C13 C15 128.59(12) . . ?
N6 C14 C16 124.21(11) . . ?
C13 C14 N6 107.52(11) . . ?
C13 C14 C16 128.26(12) . . ?
N5 C17 C18 111.60(11) . . ?
N5 C17 C19 112.36(12) . . ?
C18 C17 C19 112.34(11) . . ?
N6 C20 C21 112.82(11) . . ?
N6 C20 C22 110.84(10) . . ?
C22 C20 C21 112.65(11) . . ?
C24 C23 P1 111.40(10) . . ?
C25 C23 P1 110.65(9) . . ?
C25 C23 C24 112.28(12) . . ?

####################################################################### 
# 
# 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_i-43d_pre2
_database_code_depnum_ccdc_archive 'CCDC 1837295'
_audit_update_record             
;
2018-04-15 deposited with the CCDC.
2018-06-21 downloaded from the CCDC.
;
_audit_creation_date             2016-12-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C33 H60 N9 O2 P1 S1'
_chemical_formula_sum            'C33 H60 N9 O2 P S'
_chemical_formula_weight         677.93
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      cubic
_space_group_IT_number           220
_space_group_name_H-M_alt        'I -4 3 d'
_space_group_name_Hall           'I -4bd 2c 3'
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'
'z, x, y'
'z+1/2, -x+1/2, -y'
'-z+1/2, -x, y+1/2'
'-z, x+1/2, -y+1/2'
'y, z, x'
'-y, z+1/2, -x+1/2'
'y+1/2, -z+1/2, -x'
'-y+1/2, -z, x+1/2'
'y+1/4, x+1/4, z+1/4'
'-y+1/4, -x+3/4, z+3/4'
'y+3/4, -x+1/4, -z+3/4'
'-y+3/4, x+3/4, -z+1/4'
'x+1/4, z+1/4, y+1/4'
'-x+3/4, z+3/4, -y+1/4'
'-x+1/4, -z+3/4, y+3/4'
'x+3/4, -z+1/4, -y+3/4'
'z+1/4, y+1/4, x+1/4'
'z+3/4, -y+1/4, -x+3/4'
'-z+3/4, y+3/4, -x+1/4'
'-z+1/4, -y+3/4, x+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-x+1/2, y+1, -z+1'
'x+1, -y+1, -z+1/2'
'z+1/2, x+1/2, y+1/2'
'z+1, -x+1, -y+1/2'
'-z+1, -x+1/2, y+1'
'-z+1/2, x+1, -y+1'
'y+1/2, z+1/2, x+1/2'
'-y+1/2, z+1, -x+1'
'y+1, -z+1, -x+1/2'
'-y+1, -z+1/2, x+1'
'y+3/4, x+3/4, z+3/4'
'-y+3/4, -x+5/4, z+5/4'
'y+5/4, -x+3/4, -z+5/4'
'-y+5/4, x+5/4, -z+3/4'
'x+3/4, z+3/4, y+3/4'
'-x+5/4, z+5/4, -y+3/4'
'-x+3/4, -z+5/4, y+5/4'
'x+5/4, -z+3/4, -y+5/4'
'z+3/4, y+3/4, x+3/4'
'z+5/4, -y+3/4, -x+5/4'
'-z+5/4, y+5/4, -x+3/4'
'-z+3/4, -y+5/4, x+5/4'

_cell_length_a                   24.5396(3)
_cell_length_b                   24.5396(3)
_cell_length_c                   24.5396(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     14777.6(5)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    9462
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.192
_cell_measurement_theta_min      3.321
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.173
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0861 before and 0.0500 after correction.
The Ratio of minimum to maximum transmission is 0.9085.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             5888
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0526
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            41644
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.359
_diffrn_reflns_theta_min         3.713
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.853
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.982
_reflns_number_gt                2210
_reflns_number_total             2505
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 
;
 Flack x determined using 903 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.01(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2505
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0441
_refine_ls_restrained_S_all      1.084
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0391P)²+14.7170P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0926
_refine_ls_wR_factor_ref         0.0968
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Others
 Fixed Sof: O1(0.6667)
 Fixed Uiso: H4A(0.061) H4B(0.061) H4C(0.061) H5A(0.063) H5B(0.063) H5C(0.063)
 H6(0.032) H7A(0.058) H7B(0.058) H7C(0.058) H8A(0.053) H8B(0.053) H8C(0.053)
 H9(0.034) H10A(0.07) H10B(0.07) H10C(0.07) H11A(0.057) H11B(0.057) H11C(0.057)
 Fixed X: H4A(0.2771) H4B(0.2825) H4C(0.2803) H5A(0.4041) H5B(0.3417)
 H5C(0.3858) H6(0.3952) H7A(0.2928) H7B(0.3127) H7C(0.3437) H8A(0.3641)
 H8B(0.3342) H8C(0.3039) H9(0.523) H10A(0.4898) H10B(0.5353) H10C(0.4721)
 H11A(0.4889) H11B(0.5505) H11C(0.509)
 Fixed Y: H4A(0.5533) H4B(0.6052) H4C(0.6131) H5A(0.6398) H5B(0.622)
 H5C(0.579) H6(0.5531) H7A(0.5194) H7B(0.5088) H7C(0.4803) H8A(0.6448)
 H8B(0.6115) H8C(0.6217) H9(0.5676) H10A(0.5067) H10B(0.5448) H10C(0.5559)
 H11A(0.6546) H11B(0.6405) H11C(0.6623)
 Fixed Z: H4A(-0.0986) H4B(-0.1377) H4C(-0.073) H5A(-0.2072) H5B(-0.2007) H5C(-
 0.2221) H6(0.026) H7A(-0.0165) H7B(0.0447) H7C(-0.0051) H8A(0.0171)
 H8B(0.0645) H8C(0.0076) H9(-0.119) H10A(-0.1836) H10B(-0.2106) H10C(-0.2225)
 H11A(-0.1873) H11B(-0.171) H11C(-0.1257)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
S1 S 0.54850(4) 0.45150(4) -0.04850(4) 0.0357(4) Uani 1 3 d S T P . .
P1 P 0.49667(3) 0.50333(3) 0.00333(3) 0.0203(3) Uani 1 3 d S T P . .
O1 O 0.51786(17) 0.44845(17) -0.09918(15) 0.0445(11) Uani 0.6667 1 d . . P . .
N1 N 0.47905(11) 0.55457(11) -0.03351(11) 0.0232(6) Uani 1 1 d . . . . .
N2 N 0.38336(11) 0.56818(11) -0.05356(11) 0.0236(6) Uani 1 1 d . . . . .
N3 N 0.44254(11) 0.57950(11) -0.11908(11) 0.0243(6) Uani 1 1 d . . . . .
C1 C 0.43749(13) 0.56439(12) -0.06589(13) 0.0209(6) Uani 1 1 d . . . . .
C2 C 0.35437(14) 0.58520(13) -0.09987(13) 0.0263(8) Uani 1 1 d . . . . .
C3 C 0.39049(14) 0.59245(14) -0.14011(14) 0.0276(8) Uani 1 1 d . . . . .
C4 C 0.29325(15) 0.58959(17) -0.10253(16) 0.0405(10) Uani 1 1 d . . . . .
H4A H 0.2771 0.5533 -0.0986 0.061 Uiso 1 1 calc GR . . . .
H4B H 0.2825 0.6052 -0.1377 0.061 Uiso 1 1 calc GR . . . .
H4C H 0.2803 0.6131 -0.0730 0.061 Uiso 1 1 calc GR . . . .
C5 C 0.37959(17) 0.60979(17) -0.19747(16) 0.0418(10) Uani 1 1 d . . . . .
H5A H 0.4041 0.6398 -0.2072 0.063 Uiso 1 1 calc GR . . . .
H5B H 0.3417 0.6220 -0.2007 0.063 Uiso 1 1 calc GR . . . .
H5C H 0.3858 0.5790 -0.2221 0.063 Uiso 1 1 calc GR . . . .
C6 C 0.36287(13) 0.56192(13) 0.00281(14) 0.0271(7) Uani 1 1 d . . . . .
H6 H 0.3952 0.5531 0.0260 0.032 Uiso 1 1 calc R . . . .
C7 C 0.32462(14) 0.51327(16) 0.00681(16) 0.0384(9) Uani 1 1 d . . . . .
H7A H 0.2928 0.5194 -0.0165 0.058 Uiso 1 1 calc GR . . . .
H7B H 0.3127 0.5088 0.0447 0.058 Uiso 1 1 calc GR . . . .
H7C H 0.3437 0.4803 -0.0051 0.058 Uiso 1 1 calc GR . . . .
C8 C 0.33917(15) 0.61469(16) 0.02496(15) 0.0353(9) Uani 1 1 d . . . . .
H8A H 0.3641 0.6448 0.0171 0.053 Uiso 1 1 calc GR . . . .
H8B H 0.3342 0.6115 0.0645 0.053 Uiso 1 1 calc GR . . . .
H8C H 0.3039 0.6217 0.0076 0.053 Uiso 1 1 calc GR . . . .
C9 C 0.49589(14) 0.58180(14) -0.14592(13) 0.0285(7) Uani 1 1 d . . . . .
H9 H 0.5230 0.5676 -0.1190 0.034 Uiso 1 1 calc R . . . .
C10 C 0.49850(19) 0.54392(17) -0.19502(15) 0.0466(10) Uani 1 1 d . . . . .
H10A H 0.4898 0.5067 -0.1836 0.070 Uiso 1 1 calc GR . . . .
H10B H 0.5353 0.5448 -0.2106 0.070 Uiso 1 1 calc GR . . . .
H10C H 0.4721 0.5559 -0.2225 0.070 Uiso 1 1 calc GR . . . .
C11 C 0.51257(15) 0.63993(16) -0.15860(16) 0.0382(9) Uani 1 1 d . . . . .
H11A H 0.4889 0.6546 -0.1873 0.057 Uiso 1 1 calc GR . . . .
H11B H 0.5505 0.6405 -0.1710 0.057 Uiso 1 1 calc GR . . . .
H11C H 0.5090 0.6623 -0.1257 0.057 Uiso 1 1 calc GR . . . .


_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
S1 P1 2.203(2) . ?
S1 O1 1.455(4) 10_655 ?
S1 O1 1.455(4) . ?
S1 O1 1.455(4) 7_564 ?
P1 N1 1.608(3) 10_655 ?
P1 N1 1.608(3) 7_564 ?
P1 N1 1.608(3) . ?
N1 C1 1.315(4) . ?
N2 C1 1.365(4) . ?
N2 C2 1.404(4) . ?
N2 C6 1.480(4) . ?
N3 C1 1.363(4) . ?
N3 C3 1.414(4) . ?
N3 C9 1.467(4) . ?
C2 C3 1.339(5) . ?
C2 C4 1.505(5) . ?
C3 C5 1.495(5) . ?
C6 C7 1.522(5) . ?
C6 C8 1.520(5) . ?
C9 C10 1.523(5) . ?
C9 C11 1.516(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 P1 102.99(18) . . ?
O1 S1 P1 102.99(18) 7_564 . ?
O1 S1 P1 102.99(18) 10_655 . ?
O1 S1 O1 115.10(13) . 7_564 ?
O1 S1 O1 115.10(13) . 10_655 ?
O1 S1 O1 115.10(13) 7_564 10_655 ?
N1 P1 S1 106.39(11) . . ?
N1 P1 S1 106.39(11) 7_564 . ?
N1 P1 S1 106.39(11) 10_655 . ?
N1 P1 N1 112.37(9) . 7_564 ?
N1 P1 N1 112.37(9) . 10_655 ?
N1 P1 N1 112.37(9) 7_564 10_655 ?
C1 N1 P1 133.7(2) . . ?
C1 N2 C2 109.5(3) . . ?
C1 N2 C6 122.0(3) . . ?
C2 N2 C6 128.0(3) . . ?
C1 N3 C3 109.2(3) . . ?
C1 N3 C9 121.5(3) . . ?
C3 N3 C9 129.4(3) . . ?
N1 C1 N2 129.3(3) . . ?
N1 C1 N3 123.9(3) . . ?
N3 C1 N2 106.4(3) . . ?
N2 C2 C4 124.1(3) . . ?
C3 C2 N2 107.5(3) . . ?
C3 C2 C4 128.2(3) . . ?
N3 C3 C5 124.7(3) . . ?
C2 C3 N3 107.4(3) . . ?
C2 C3 C5 127.9(3) . . ?
N2 C6 C7 110.6(3) . . ?
N2 C6 C8 112.1(3) . . ?
C8 C6 C7 114.2(3) . . ?
N3 C9 C10 111.7(3) . . ?
N3 C9 C11 111.7(3) . . ?
C11 C9 C10 113.6(3) . . ?

####################################################################### 
# 
# 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_p21n_pre
_database_code_depnum_ccdc_archive 'CCDC 1837297'
_audit_update_record             
;
2018-04-15 deposited with the CCDC.
2018-06-21 downloaded from the CCDC.
;
_audit_creation_date             2016-08-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C12 H27 O3 P S'
_chemical_formula_sum            'C12 H27 O3 P S'
_chemical_formula_weight         282.36
_chemical_melting_point          ?
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'
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.04457(8)
_cell_length_b                   13.70329(14)
_cell_length_c                   13.50419(12)
_cell_angle_alpha                90
_cell_angle_beta                 91.7658(4)
_cell_angle_gamma                90
_cell_volume                     1487.96(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9998
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.498
_cell_measurement_theta_min      3.018
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.321
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9475
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0541 before and 0.0279 after correction.
The Ratio of minimum to maximum transmission is 0.9475.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0165
_diffrn_reflns_av_unetI/netI     0.0153
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16409
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.509
_diffrn_reflns_theta_min         3.907
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4246
_reflns_number_total             4532
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.418
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         4532
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0262
_refine_ls_R_factor_gt           0.0244
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0370P)²+0.5018P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0693
_refine_ls_wR_factor_ref         0.0708
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2.a Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C4(H4A,H4B,H4C), C6(H6A,H6B,H6C), C7(H7A,
 H7B,H7C), C8(H8A,H8B,H8C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,
 H12B,H12C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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
S1 S 0.44045(3) 0.79302(2) 0.22486(2) 0.01233(6) Uani 1 1 d . . . . .
P1 P 0.57756(3) 0.65447(2) 0.24592(2) 0.00776(6) Uani 1 1 d . . . . .
O1 O 0.36491(9) 0.80927(5) 0.31938(5) 0.01969(14) Uani 1 1 d . . . . .
O2 O 0.32343(9) 0.77135(5) 0.14424(5) 0.01801(14) Uani 1 1 d . . . . .
O3 O 0.56871(9) 0.86240(5) 0.20104(5) 0.01916(14) Uani 1 1 d . . . . .
C1 C 0.41836(10) 0.55341(6) 0.23657(6) 0.01113(14) Uani 1 1 d . . . . .
C2 C 0.35888(12) 0.53684(7) 0.12826(6) 0.01672(17) Uani 1 1 d . . . . .
H2A H 0.3157 0.5982 0.1004 0.025 Uiso 1 1 calc GR . . . .
H2B H 0.2707 0.4875 0.1261 0.025 Uiso 1 1 calc GR . . . .
H2C H 0.4524 0.5143 0.0894 0.025 Uiso 1 1 calc GR . . . .
C3 C 0.49206(11) 0.45716(6) 0.27691(6) 0.01478(16) Uani 1 1 d . . . . .
H3A H 0.5956 0.4428 0.2435 0.022 Uiso 1 1 calc GR . . . .
H3B H 0.4124 0.4041 0.2646 0.022 Uiso 1 1 calc GR . . . .
H3C H 0.5151 0.4633 0.3483 0.022 Uiso 1 1 calc GR . . . .
C4 C 0.26194(11) 0.57954(7) 0.29408(7) 0.01684(17) Uani 1 1 d . . . . .
H4A H 0.2923 0.5881 0.3644 0.025 Uiso 1 1 calc GR . . . .
H4B H 0.1802 0.5268 0.2867 0.025 Uiso 1 1 calc GR . . . .
H4C H 0.2139 0.6403 0.2678 0.025 Uiso 1 1 calc GR . . . .
C5 C 0.73199(11) 0.64837(6) 0.14331(6) 0.01143(15) Uani 1 1 d . . . . .
C6 C 0.65097(12) 0.68405(7) 0.04477(6) 0.01476(16) Uani 1 1 d . . . . .
H6A H 0.5525 0.6444 0.0286 0.022 Uiso 1 1 calc GR . . . .
H6B H 0.7308 0.6779 -0.0082 0.022 Uiso 1 1 calc GR . . . .
H6C H 0.6182 0.7526 0.0513 0.022 Uiso 1 1 calc GR . . . .
C7 C 0.87953(11) 0.71673(7) 0.16591(7) 0.01719(17) Uani 1 1 d . . . . .
H7A H 0.8388 0.7835 0.1742 0.026 Uiso 1 1 calc GR . . . .
H7B H 0.9562 0.7147 0.1109 0.026 Uiso 1 1 calc GR . . . .
H7C H 0.9378 0.6956 0.2270 0.026 Uiso 1 1 calc GR . . . .
C8 C 0.79913(12) 0.54399(7) 0.13000(7) 0.01643(17) Uani 1 1 d . . . . .
H8A H 0.8443 0.5198 0.1936 0.025 Uiso 1 1 calc GR . . . .
H8B H 0.8871 0.5446 0.0814 0.025 Uiso 1 1 calc GR . . . .
H8C H 0.7086 0.5012 0.1065 0.025 Uiso 1 1 calc GR . . . .
C9 C 0.68162(11) 0.66138(6) 0.37317(6) 0.01104(14) Uani 1 1 d . . . . .
C10 C 0.75326(13) 0.76459(7) 0.39167(6) 0.01792(17) Uani 1 1 d . . . . .
H10A H 0.8389 0.7782 0.3435 0.027 Uiso 1 1 calc GR . . . .
H10B H 0.8025 0.7681 0.4589 0.027 Uiso 1 1 calc GR . . . .
H10C H 0.6639 0.8129 0.3844 0.027 Uiso 1 1 calc GR . . . .
C11 C 0.82182(11) 0.58557(7) 0.38673(6) 0.01616(16) Uani 1 1 d . . . . .
H11A H 0.7771 0.5201 0.3740 0.024 Uiso 1 1 calc GR . . . .
H11B H 0.8678 0.5890 0.4547 0.024 Uiso 1 1 calc GR . . . .
H11C H 0.9098 0.5994 0.3401 0.024 Uiso 1 1 calc GR . . . .
C12 C 0.55427(12) 0.64414(6) 0.45412(6) 0.01454(16) Uani 1 1 d . . . . .
H12A H 0.4603 0.6890 0.4441 0.022 Uiso 1 1 calc GR . . . .
H12B H 0.6072 0.6558 0.5194 0.022 Uiso 1 1 calc GR . . . .
H12C H 0.5142 0.5767 0.4504 0.022 Uiso 1 1 calc GR . . . .


_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
S1 P1 2.2098(3) . ?
S1 O1 1.4477(7) . ?
S1 O2 1.4479(7) . ?
S1 O3 1.4465(7) . ?
P1 C1 1.8878(8) . ?
P1 C5 1.8910(8) . ?
P1 C9 1.8906(8) . ?
C1 C2 1.5416(12) . ?
C1 C3 1.5388(12) . ?
C1 C4 1.5411(12) . ?
C5 C6 1.5432(11) . ?
C5 C7 1.5353(12) . ?
C5 C8 1.5413(12) . ?
C9 C10 1.5447(12) . ?
C9 C11 1.5401(12) . ?
C9 C12 1.5393(12) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 P1 103.89(3) . . ?
O1 S1 O2 114.43(4) . . ?
O2 S1 P1 103.35(3) . . ?
O3 S1 P1 103.69(3) . . ?
O3 S1 O1 114.62(4) . . ?
O3 S1 O2 114.79(4) . . ?
C1 P1 S1 106.66(3) . . ?
C1 P1 C5 112.22(4) . . ?
C1 P1 C9 112.21(4) . . ?
C5 P1 S1 106.27(3) . . ?
C9 P1 S1 106.21(3) . . ?
C9 P1 C5 112.69(4) . . ?
C2 C1 P1 111.20(6) . . ?
C3 C1 P1 110.60(6) . . ?
C3 C1 C2 108.34(7) . . ?
C3 C1 C4 109.41(7) . . ?
C4 C1 P1 111.02(6) . . ?
C4 C1 C2 106.14(7) . . ?
C6 C5 P1 110.39(6) . . ?
C7 C5 P1 110.41(6) . . ?
C7 C5 C6 106.34(7) . . ?
C7 C5 C8 108.53(7) . . ?
C8 C5 P1 111.53(6) . . ?
C8 C5 C6 109.49(7) . . ?
C10 C9 P1 110.21(5) . . ?
C11 C9 P1 112.11(6) . . ?
C11 C9 C10 109.28(7) . . ?
C12 C9 P1 110.61(6) . . ?
C12 C9 C10 106.19(7) . . ?
C12 C9 C11 108.24(7) . . ?

####################################################################### 
# 
# 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_p212121
_database_code_depnum_ccdc_archive 'CCDC 1837296'
_audit_update_record             
;
2018-04-15 deposited with the CCDC.
2018-06-21 downloaded from the CCDC.
;
_audit_creation_date             2017-12-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C17 H34 N3 O3 P S'
_chemical_formula_sum            'C17 H34 N3 O3 P S'
_chemical_formula_weight         391.50
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   9.35040(10)
_cell_length_b                   9.84690(10)
_cell_length_c                   22.5631(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2077.44(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9945
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.486
_cell_measurement_theta_min      2.256
_shelx_estimated_absorpt_T_max   0.949
_shelx_estimated_absorpt_T_min   0.869
_exptl_absorpt_coefficient_mu    0.253
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9030
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1064 before and 0.0410 after correction. The Ratio of minimum to maximum transmission is 0.9030. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.21
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_unetI/netI     0.0157
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            37810
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.486
_diffrn_reflns_theta_min         1.805
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.773
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                6212
_reflns_number_total             6329
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 
;
 Flack x determined using 2696 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.002(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         6329
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0223
_refine_ls_R_factor_gt           0.0219
_refine_ls_restrained_S_all      1.097
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0327P)²+0.3504P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0607
_refine_ls_wR_factor_ref         0.0610
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C9(H9), C12(H12), C15(H15)
2.b Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C10(H10A,
 H10B,H10C), C11(H11A,H11B,H11C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C),
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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
S1 S 0.79770(3) 0.86471(3) 0.65674(2) 0.01279(6) Uani 1 1 d . . . . .
P1 P 0.80732(3) 0.65925(3) 0.69261(2) 0.01020(6) Uani 1 1 d . . . . .
O1 O 0.71311(12) 0.93742(10) 0.70042(5) 0.0212(2) Uani 1 1 d . . . . .
O2 O 0.94449(11) 0.91134(10) 0.65174(5) 0.01851(19) Uani 1 1 d . . . . .
O3 O 0.72664(11) 0.84405(11) 0.60013(4) 0.0195(2) Uani 1 1 d . . . . .
N1 N 0.83059(12) 0.54173(11) 0.64591(5) 0.0129(2) Uani 1 1 d . . . . .
N2 N 0.88484(12) 0.57401(11) 0.54250(5) 0.01244(19) Uani 1 1 d . . . . .
N3 N 0.71214(12) 0.43282(10) 0.56512(5) 0.01249(19) Uani 1 1 d . . . . .
C1 C 0.80739(14) 0.52274(12) 0.58835(5) 0.0113(2) Uani 1 1 d . . . . .
C2 C 0.83861(14) 0.51335(13) 0.48957(5) 0.0140(2) Uani 1 1 d . . . . .
C3 C 0.73179(14) 0.42617(13) 0.50358(6) 0.0145(2) Uani 1 1 d . . . . .
C4 C 0.89199(16) 0.55150(16) 0.42969(6) 0.0203(3) Uani 1 1 d . . . . .
H4A H 0.8511 0.6392 0.4181 0.030 Uiso 1 1 calc GR . . . .
H4B H 0.8635 0.4820 0.4009 0.030 Uiso 1 1 calc GR . . . .
H4C H 0.9965 0.5584 0.4306 0.030 Uiso 1 1 calc GR . . . .
C5 C 0.63802(16) 0.34714(16) 0.46264(6) 0.0215(3) Uani 1 1 d . . . . .
H5A H 0.6327 0.2526 0.4761 0.032 Uiso 1 1 calc GR . . . .
H5B H 0.6779 0.3501 0.4225 0.032 Uiso 1 1 calc GR . . . .
H5C H 0.5419 0.3868 0.4625 0.032 Uiso 1 1 calc GR . . . .
C6 C 1.01116(13) 0.66077(14) 0.55228(5) 0.0136(2) Uani 1 1 d . . . . .
H6 H 1.0051 0.6939 0.5941 0.016 Uiso 1 1 calc R . . . .
C7 C 1.14712(15) 0.57583(15) 0.54803(7) 0.0197(3) Uani 1 1 d . . . . .
H7A H 1.1382 0.4958 0.5736 0.030 Uiso 1 1 calc GR . . . .
H7B H 1.2291 0.6303 0.5609 0.030 Uiso 1 1 calc GR . . . .
H7C H 1.1614 0.5468 0.5069 0.030 Uiso 1 1 calc GR . . . .
C8 C 1.01308(16) 0.78631(15) 0.51303(6) 0.0193(3) Uani 1 1 d . . . . .
H8A H 1.0367 0.7600 0.4723 0.029 Uiso 1 1 calc GR . . . .
H8B H 1.0851 0.8503 0.5277 0.029 Uiso 1 1 calc GR . . . .
H8C H 0.9187 0.8296 0.5138 0.029 Uiso 1 1 calc GR . . . .
C9 C 0.62481(14) 0.34338(14) 0.60279(6) 0.0164(2) Uani 1 1 d . . . . .
H9 H 0.6329 0.3789 0.6442 0.020 Uiso 1 1 calc R . . . .
C10 C 0.46649(15) 0.34739(18) 0.58655(7) 0.0248(3) Uani 1 1 d . . . . .
H10A H 0.4376 0.4415 0.5791 0.037 Uiso 1 1 calc GR . . . .
H10B H 0.4099 0.3102 0.6193 0.037 Uiso 1 1 calc GR . . . .
H10C H 0.4503 0.2931 0.5508 0.037 Uiso 1 1 calc GR . . . .
C11 C 0.6859(2) 0.19995(15) 0.60334(8) 0.0269(3) Uani 1 1 d . . . . .
H11A H 0.6724 0.1582 0.5643 0.040 Uiso 1 1 calc GR . . . .
H11B H 0.6365 0.1458 0.6335 0.040 Uiso 1 1 calc GR . . . .
H11C H 0.7883 0.2037 0.6126 0.040 Uiso 1 1 calc GR . . . .
C12 C 0.63884(14) 0.64145(16) 0.73315(6) 0.0180(2) Uani 1 1 d . . . . .
H12 H 0.6329 0.7171 0.7626 0.022 Uiso 1 1 calc R . . . .
C13 C 0.51052(14) 0.65344(17) 0.69128(7) 0.0238(3) Uani 1 1 d . . . . .
H13A H 0.5079 0.7449 0.6742 0.036 Uiso 1 1 calc GR . . . .
H13B H 0.4221 0.6368 0.7134 0.036 Uiso 1 1 calc GR . . . .
H13C H 0.5195 0.5863 0.6594 0.036 Uiso 1 1 calc GR . . . .
C14 C 0.63785(19) 0.50678(18) 0.76736(7) 0.0260(3) Uani 1 1 d . . . . .
H14A H 0.6552 0.4316 0.7398 0.039 Uiso 1 1 calc GR . . . .
H14B H 0.5446 0.4945 0.7865 0.039 Uiso 1 1 calc GR . . . .
H14C H 0.7131 0.5082 0.7976 0.039 Uiso 1 1 calc GR . . . .
C15 C 0.95147(14) 0.65159(15) 0.74654(6) 0.0154(2) Uani 1 1 d . . . . .
H15 H 0.9459 0.5603 0.7658 0.018 Uiso 1 1 calc R . . . .
C16 C 1.09908(14) 0.66176(16) 0.71792(6) 0.0206(3) Uani 1 1 d . . . . .
H16A H 1.1069 0.5946 0.6860 0.031 Uiso 1 1 calc GR . . . .
H16B H 1.1728 0.6442 0.7478 0.031 Uiso 1 1 calc GR . . . .
H16C H 1.1123 0.7531 0.7015 0.031 Uiso 1 1 calc GR . . . .
C17 C 0.93218(18) 0.75755(17) 0.79582(6) 0.0235(3) Uani 1 1 d . . . . .
H17A H 0.9339 0.8488 0.7785 0.035 Uiso 1 1 calc GR . . . .
H17B H 1.0100 0.7487 0.8247 0.035 Uiso 1 1 calc GR . . . .
H17C H 0.8403 0.7427 0.8157 0.035 Uiso 1 1 calc GR . . . .


_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
S1 P1 2.1809(4) . ?
S1 O1 1.4524(10) . ?
S1 O2 1.4518(11) . ?
S1 O3 1.4540(10) . ?
P1 N1 1.5799(11) . ?
P1 C12 1.8302(13) . ?
P1 C15 1.8175(13) . ?
N1 C1 1.3301(15) . ?
N2 C1 1.3599(15) . ?
N2 C2 1.4036(16) . ?
N2 C6 1.4743(16) . ?
N3 C1 1.3608(15) . ?
N3 C3 1.4021(16) . ?
N3 C9 1.4713(17) . ?
C2 C3 1.3545(19) . ?
C2 C4 1.4884(18) . ?
C3 C5 1.4926(18) . ?
C6 C7 1.5247(19) . ?
C6 C8 1.5207(19) . ?
C9 C10 1.526(2) . ?
C9 C11 1.524(2) . ?
C12 C13 1.532(2) . ?
C12 C14 1.534(2) . ?
C15 C16 1.5271(19) . ?
C15 C17 1.535(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 P1 103.18(4) . . ?
O1 S1 O3 114.59(6) . . ?
O2 S1 P1 106.45(4) . . ?
O2 S1 O1 114.31(7) . . ?
O2 S1 O3 114.08(6) . . ?
O3 S1 P1 102.42(5) . . ?
N1 P1 S1 115.95(4) . . ?
N1 P1 C12 112.44(6) . . ?
N1 P1 C15 108.30(6) . . ?
C12 P1 S1 103.81(5) . . ?
C15 P1 S1 108.52(5) . . ?
C15 P1 C12 107.44(6) . . ?
C1 N1 P1 137.03(10) . . ?
C1 N2 C2 108.98(10) . . ?
C1 N2 C6 121.87(10) . . ?
C2 N2 C6 128.36(10) . . ?
C1 N3 C3 109.03(10) . . ?
C1 N3 C9 122.03(10) . . ?
C3 N3 C9 128.08(11) . . ?
N1 C1 N2 127.13(12) . . ?
N1 C1 N3 125.05(11) . . ?
N2 C1 N3 107.29(10) . . ?
N2 C2 C4 124.17(12) . . ?
C3 C2 N2 107.35(11) . . ?
C3 C2 C4 128.25(12) . . ?
N3 C3 C5 124.08(12) . . ?
C2 C3 N3 107.35(11) . . ?
C2 C3 C5 128.25(12) . . ?
N2 C6 C7 109.92(11) . . ?
N2 C6 C8 113.16(11) . . ?
C8 C6 C7 113.55(11) . . ?
N3 C9 C10 112.60(11) . . ?
N3 C9 C11 110.57(12) . . ?
C11 C9 C10 112.95(12) . . ?
C13 C12 P1 111.01(9) . . ?
C13 C12 C14 111.85(13) . . ?
C14 C12 P1 109.84(11) . . ?
C16 C15 P1 112.61(9) . . ?
C16 C15 C17 111.58(12) . . ?
C17 C15 P1 111.68(10) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
