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

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

data_C
_database_code_depnum_ccdc_archive 'CCDC 1058984'
_audit_update_record             
;
2015-04-10 deposited with the CCDC.
2016-01-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H20 P, C17 H14 N O3 S, 0.7(H2 O)'
_chemical_formula_sum            'C41 H35.40 N O3.70 P S'
_chemical_formula_weight         664.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

_cell_length_a                   14.3436(10)
_cell_length_b                   13.8575(9)
_cell_length_c                   18.0804(12)
_cell_angle_alpha                90
_cell_angle_beta                 112.786(2)
_cell_angle_gamma                90
_cell_volume                     3313.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    90.0(5)
_cell_measurement_reflns_used    9289
_cell_measurement_theta_min      3.34
_cell_measurement_theta_max      68.37

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1396
_exptl_absorpt_coefficient_mu    1.673
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5806
_exptl_absorpt_correction_T_max  0.8919
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      90.0(5)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'I\mS microfocus'
_diffrn_radiation_monochromator  'QUAZAR multilayer optics'
_diffrn_measurement_device_type  'Bruker Kappa APEX-II DUO'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            42167
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_av_sigmaI/netI    0.0674
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.34
_diffrn_reflns_theta_max         68.77
_reflns_number_total             5810
_reflns_number_gt                5188
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_refine_special_details          SQUEEZE

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0796P)²+2.5341P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5810
_refine_ls_number_parameters     428
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0493
_refine_ls_wR_factor_ref         0.1445
_refine_ls_wR_factor_gt          0.1420
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.19661(4) 0.93319(4) 0.14146(3) 0.02344(16) Uani 1 1 d . . .
O1 O 0.22438(13) 0.87171(12) 0.08766(10) 0.0299(4) Uani 1 1 d . . .
O2 O 0.08927(12) 0.95385(12) 0.11146(10) 0.0315(4) Uani 1 1 d . . .
O3 O 0.26064(14) 1.01792(12) 0.16625(11) 0.0365(4) Uani 1 1 d . . .
N1 N 0.41655(16) 0.64478(16) 0.56919(12) 0.0306(4) Uani 1 1 d . . .
H1N H 0.365(2) 0.621(2) 0.5739(18) 0.037 Uiso 1 1 d . . .
C1 C 0.22359(17) 0.86388(17) 0.23015(14) 0.0266(5) Uani 1 1 d . . .
C2 C 0.14636(17) 0.81469(16) 0.24500(13) 0.0251(5) Uani 1 1 d . . .
H2 H 0.0785 0.8185 0.2071 0.030 Uiso 1 1 calc R . .
C3 C 0.16834(17) 0.76154(16) 0.31362(13) 0.0245(5) Uani 1 1 d . . .
H3 H 0.1154 0.7295 0.3230 0.029 Uiso 1 1 calc R . .
C4 C 0.26887(18) 0.75370(17) 0.37066(14) 0.0271(5) Uani 1 1 d . . .
C5 C 0.29478(18) 0.70265(16) 0.44393(14) 0.0263(5) Uani 1 1 d . . .
H5 H 0.2431 0.6720 0.4559 0.032 Uiso 1 1 calc R . .
C6 C 0.39379(18) 0.69670(18) 0.49810(14) 0.0304(5) Uani 1 1 d . . .
C7 C 0.4712(2) 0.7407(3) 0.47893(16) 0.0467(7) Uani 1 1 d . . .
H7 H 0.5399 0.7340 0.5145 0.056 Uiso 1 1 calc R . .
C8 C 0.4478(2) 0.7922(3) 0.41019(19) 0.0573(10) Uani 1 1 d . . .
H8 H 0.5005 0.8224 0.3993 0.069 Uiso 1 1 calc R . .
C9 C 0.34640(19) 0.8020(2) 0.35410(16) 0.0402(6) Uani 1 1 d . . .
C10 C 0.32107(19) 0.8575(2) 0.28373(16) 0.0391(6) Uani 1 1 d . . .
H10 H 0.3727 0.8910 0.2736 0.047 Uiso 1 1 calc R . .
C11 C 0.49161(17) 0.66913(18) 0.64410(14) 0.0277(5) Uani 1 1 d . . .
C12 C 0.51399(18) 0.60149(17) 0.70585(14) 0.0275(5) Uani 1 1 d . . .
H12 H 0.4838 0.5393 0.6947 0.033 Uiso 1 1 calc R . .
C13 C 0.57997(18) 0.62412(18) 0.78349(14) 0.0281(5) Uani 1 1 d . . .
H13 H 0.5938 0.5771 0.8246 0.034 Uiso 1 1 calc R . .
C14 C 0.62622(18) 0.71440(19) 0.80214(15) 0.0313(5) Uani 1 1 d . . .
C15 C 0.60692(19) 0.78006(19) 0.73984(16) 0.0353(6) Uani 1 1 d . . .
H15 H 0.6397 0.8411 0.7506 0.042 Uiso 1 1 calc R . .
C16 C 0.54060(18) 0.75825(18) 0.66205(16) 0.0341(6) Uani 1 1 d . . .
H16 H 0.5285 0.8046 0.6207 0.041 Uiso 1 1 calc R . .
C17 C 0.6906(2) 0.7423(2) 0.88710(16) 0.0406(6) Uani 1 1 d . . .
H17A H 0.6470 0.7611 0.9151 0.061 Uiso 1 1 calc R . .
H17B H 0.7341 0.7968 0.8868 0.061 Uiso 1 1 calc R . .
H17C H 0.7327 0.6873 0.9147 0.061 Uiso 1 1 calc R . .
P1 P 0.09622(4) 0.47965(4) 0.19390(3) 0.02232(16) Uani 1 1 d . . .
C18 C 0.05375(17) 0.36294(15) 0.15127(13) 0.0236(4) Uani 1 1 d . . .
C19 C 0.11089(18) 0.28091(16) 0.18563(14) 0.0266(5) Uani 1 1 d . . .
H19 H 0.1666 0.2851 0.2358 0.032 Uiso 1 1 calc R . .
C20 C 0.08531(19) 0.19298(17) 0.14555(15) 0.0301(5) Uani 1 1 d . . .
H20 H 0.1241 0.1370 0.1683 0.036 Uiso 1 1 calc R . .
C21 C 0.00363(18) 0.18649(17) 0.07257(14) 0.0285(5) Uani 1 1 d . . .
H21 H -0.0127 0.1264 0.0452 0.034 Uiso 1 1 calc R . .
C22 C -0.05439(18) 0.26781(17) 0.03943(14) 0.0279(5) Uani 1 1 d . . .
H22 H -0.1113 0.2629 -0.0099 0.033 Uiso 1 1 calc R . .
C23 C -0.02919(18) 0.35608(17) 0.07847(14) 0.0269(5) Uani 1 1 d . . .
H23 H -0.0684 0.4117 0.0556 0.032 Uiso 1 1 calc R . .
C24 C -0.01189(17) 0.55891(16) 0.16421(13) 0.0244(5) Uani 1 1 d . . .
C25 C -0.01273(18) 0.64420(16) 0.12281(13) 0.0268(5) Uani 1 1 d . . .
H25 H 0.0441 0.6613 0.1109 0.032 Uiso 1 1 calc R . .
C26 C -0.09684(19) 0.70367(17) 0.09919(14) 0.0306(5) Uani 1 1 d . . .
H26 H -0.0980 0.7612 0.0702 0.037 Uiso 1 1 calc R . .
C27 C -0.17899(19) 0.68008(18) 0.11740(14) 0.0327(5) Uani 1 1 d . . .
H27 H -0.2359 0.7218 0.1018 0.039 Uiso 1 1 calc R . .
C28 C -0.17852(19) 0.59542(19) 0.15855(15) 0.0325(5) Uani 1 1 d . . .
H28 H -0.2350 0.5795 0.1713 0.039 Uiso 1 1 calc R . .
C29 C -0.09563(18) 0.53397(17) 0.18110(14) 0.0285(5) Uani 1 1 d . . .
H29 H -0.0961 0.4752 0.2080 0.034 Uiso 1 1 calc R . .
C30 C 0.16030(17) 0.47139(15) 0.30088(13) 0.0242(5) Uani 1 1 d . . .
C31 C 0.10672(18) 0.47841(16) 0.35133(14) 0.0264(5) Uani 1 1 d . . .
H31 H 0.0361 0.4911 0.3292 0.032 Uiso 1 1 calc R . .
C32 C 0.15679(19) 0.46687(16) 0.43303(14) 0.0289(5) Uani 1 1 d . . .
H32 H 0.1202 0.4700 0.4669 0.035 Uiso 1 1 calc R . .
C33 C 0.26031(19) 0.45067(16) 0.46595(14) 0.0291(5) Uani 1 1 d . . .
H33 H 0.2947 0.4443 0.5224 0.035 Uiso 1 1 calc R . .
C34 C 0.31366(19) 0.44381(17) 0.41626(15) 0.0307(5) Uani 1 1 d . . .
H34 H 0.3846 0.4328 0.4389 0.037 Uiso 1 1 calc R . .
C35 C 0.26378(18) 0.45292(17) 0.33374(14) 0.0288(5) Uani 1 1 d . . .
H35 H 0.3001 0.4466 0.2998 0.035 Uiso 1 1 calc R . .
C36 C 0.18318(17) 0.52485(16) 0.15220(14) 0.0250(5) Uani 1 1 d . . .
C37 C 0.18393(18) 0.48416(17) 0.08188(14) 0.0280(5) Uani 1 1 d . . .
H37 H 0.1416 0.4307 0.0578 0.034 Uiso 1 1 calc R . .
C38 C 0.24708(18) 0.52244(19) 0.04726(15) 0.0320(5) Uani 1 1 d . . .
H38 H 0.2480 0.4949 -0.0006 0.038 Uiso 1 1 calc R . .
C39 C 0.30859(19) 0.60046(19) 0.08212(15) 0.0327(5) Uani 1 1 d . . .
H39 H 0.3509 0.6268 0.0578 0.039 Uiso 1 1 calc R . .
C40 C 0.30873(19) 0.64048(18) 0.15269(17) 0.0350(6) Uani 1 1 d . . .
H40 H 0.3514 0.6938 0.1766 0.042 Uiso 1 1 calc R . .
C41 C 0.24633(19) 0.60249(17) 0.18841(16) 0.0306(5) Uani 1 1 d . . .
H41 H 0.2468 0.6292 0.2369 0.037 Uiso 1 1 calc R . .


_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 O2 1.4491(17) . ?
S1 O3 1.4506(17) . ?
S1 O1 1.4598(17) . ?
S1 C1 1.778(2) . ?
N1 C6 1.397(3) . ?
N1 C11 1.406(3) . ?
N1 H1N 0.84(3) . ?
C1 C10 1.361(4) . ?
C1 C2 1.412(3) . ?
C2 C3 1.370(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.415(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.419(3) . ?
C4 C9 1.425(4) . ?
C5 C6 1.380(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.422(4) . ?
C7 C8 1.358(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.421(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.409(4) . ?
C10 H10 0.9500 . ?
C11 C16 1.395(4) . ?
C11 C12 1.397(3) . ?
C12 C13 1.391(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.395(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.390(4) . ?
C14 C17 1.504(4) . ?
C15 C16 1.392(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
P1 C18 1.794(2) . ?
P1 C30 1.795(2) . ?
P1 C36 1.801(2) . ?
P1 C24 1.804(2) . ?
C18 C23 1.394(3) . ?
C18 C19 1.398(3) . ?
C19 C20 1.392(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.387(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.391(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.388(3) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 C29 1.393(3) . ?
C24 C25 1.396(3) . ?
C25 C26 1.385(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.380(4) . ?
C26 H26 0.9500 . ?
C27 C28 1.388(4) . ?
C27 H27 0.9500 . ?
C28 C29 1.389(3) . ?
C28 H28 0.9500 . ?
C29 H29 0.9500 . ?
C30 C35 1.392(3) . ?
C30 C31 1.405(3) . ?
C31 C32 1.379(3) . ?
C31 H31 0.9500 . ?
C32 C33 1.387(4) . ?
C32 H32 0.9500 . ?
C33 C34 1.391(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.388(3) . ?
C34 H34 0.9500 . ?
C35 H35 0.9500 . ?
C36 C37 1.395(3) . ?
C36 C41 1.395(3) . ?
C37 C38 1.390(3) . ?
C37 H37 0.9500 . ?
C38 C39 1.383(4) . ?
C38 H38 0.9500 . ?
C39 C40 1.391(4) . ?
C39 H39 0.9500 . ?
C40 C41 1.394(3) . ?
C40 H40 0.9500 . ?
C41 H41 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O3 114.18(10) . . ?
O2 S1 O1 112.98(10) . . ?
O3 S1 O1 112.01(11) . . ?
O2 S1 C1 105.84(10) . . ?
O3 S1 C1 105.54(11) . . ?
O1 S1 C1 105.39(10) . . ?
C6 N1 C11 125.6(2) . . ?
C6 N1 H1N 113(2) . . ?
C11 N1 H1N 112(2) . . ?
C10 C1 C2 119.9(2) . . ?
C10 C1 S1 118.79(18) . . ?
C2 C1 S1 121.28(18) . . ?
C3 C2 C1 120.6(2) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 120.9(2) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C3 C4 C5 122.9(2) . . ?
C3 C4 C9 117.9(2) . . ?
C5 C4 C9 119.1(2) . . ?
C6 C5 C4 121.2(2) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 N1 119.5(2) . . ?
C5 C6 C7 119.2(2) . . ?
N1 C6 C7 121.3(2) . . ?
C8 C7 C6 120.6(2) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C9 121.7(3) . . ?
C7 C8 H8 119.1 . . ?
C9 C8 H8 119.1 . . ?
C10 C9 C8 122.1(2) . . ?
C10 C9 C4 119.8(2) . . ?
C8 C9 C4 118.1(2) . . ?
C1 C10 C9 120.8(2) . . ?
C1 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C16 C11 C12 118.0(2) . . ?
C16 C11 N1 124.4(2) . . ?
C12 C11 N1 117.5(2) . . ?
C13 C12 C11 120.7(2) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 121.3(2) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 H13 119.3 . . ?
C15 C14 C13 117.7(2) . . ?
C15 C14 C17 120.7(2) . . ?
C13 C14 C17 121.6(2) . . ?
C14 C15 C16 121.4(2) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 H15 119.3 . . ?
C15 C16 C11 120.8(2) . . ?
C15 C16 H16 119.6 . . ?
C11 C16 H16 119.6 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C18 P1 C30 110.64(10) . . ?
C18 P1 C36 107.97(10) . . ?
C30 P1 C36 108.94(11) . . ?
C18 P1 C24 108.14(11) . . ?
C30 P1 C24 112.45(10) . . ?
C36 P1 C24 108.57(10) . . ?
C23 C18 C19 120.2(2) . . ?
C23 C18 P1 119.40(17) . . ?
C19 C18 P1 119.94(17) . . ?
C20 C19 C18 119.3(2) . . ?
C20 C19 H19 120.4 . . ?
C18 C19 H19 120.4 . . ?
C21 C20 C19 120.5(2) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C20 C21 C22 120.1(2) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C23 C22 C21 120.0(2) . . ?
C23 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C22 C23 C18 119.9(2) . . ?
C22 C23 H23 120.0 . . ?
C18 C23 H23 120.0 . . ?
C29 C24 C25 119.9(2) . . ?
C29 C24 P1 119.91(17) . . ?
C25 C24 P1 120.19(18) . . ?
C26 C25 C24 119.6(2) . . ?
C26 C25 H25 120.2 . . ?
C24 C25 H25 120.2 . . ?
C27 C26 C25 120.5(2) . . ?
C27 C26 H26 119.7 . . ?
C25 C26 H26 119.7 . . ?
C26 C27 C28 120.1(2) . . ?
C26 C27 H27 120.0 . . ?
C28 C27 H27 120.0 . . ?
C27 C28 C29 120.1(2) . . ?
C27 C28 H28 120.0 . . ?
C29 C28 H28 120.0 . . ?
C28 C29 C24 119.8(2) . . ?
C28 C29 H29 120.1 . . ?
C24 C29 H29 120.1 . . ?
C35 C30 C31 119.8(2) . . ?
C35 C30 P1 119.20(17) . . ?
C31 C30 P1 120.96(18) . . ?
C32 C31 C30 119.9(2) . . ?
C32 C31 H31 120.1 . . ?
C30 C31 H31 120.1 . . ?
C31 C32 C33 120.3(2) . . ?
C31 C32 H32 119.8 . . ?
C33 C32 H32 119.8 . . ?
C32 C33 C34 119.9(2) . . ?
C32 C33 H33 120.0 . . ?
C34 C33 H33 120.0 . . ?
C35 C34 C33 120.3(2) . . ?
C35 C34 H34 119.8 . . ?
C33 C34 H34 119.8 . . ?
C34 C35 C30 119.7(2) . . ?
C34 C35 H35 120.1 . . ?
C30 C35 H35 120.1 . . ?
C37 C36 C41 120.4(2) . . ?
C37 C36 P1 119.48(18) . . ?
C41 C36 P1 120.03(17) . . ?
C38 C37 C36 119.5(2) . . ?
C38 C37 H37 120.2 . . ?
C36 C37 H37 120.2 . . ?
C39 C38 C37 120.3(2) . . ?
C39 C38 H38 119.8 . . ?
C37 C38 H38 119.8 . . ?
C38 C39 C40 120.3(2) . . ?
C38 C39 H39 119.9 . . ?
C40 C39 H39 119.9 . . ?
C39 C40 C41 120.1(2) . . ?
C39 C40 H40 120.0 . . ?
C41 C40 H40 120.0 . . ?
C40 C41 C36 119.4(2) . . ?
C40 C41 H41 120.3 . . ?
C36 C41 H41 120.3 . . ?

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 H1N O1 0.84(3) 2.13(3) 2.911(3) 155(3) 4_576

_diffrn_measured_fraction_theta_max 0.947
_diffrn_reflns_theta_full        66.50
_diffrn_measured_fraction_theta_full 0.978
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.485
_refine_diff_density_rms         0.080

# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.500 0.000 0.500 69 12 ' '
2 0.522 0.091 0.132 21 1 ' '
3 0.522 0.409 0.632 21 1 ' '
4 0.500 0.500 1.000 69 12 ' '
5 0.478 0.591 0.368 21 1 ' '
6 0.478 0.909 0.868 21 1 ' '
_platon_squeeze_details          
;
The 28 electrons per cell removed by SQUEEZE correspond to 2.8
disordered water molecules, or 0.7 per formula unit of the CIF.
The solvent is included in the formula, FW, density, etc., but 
is not in the model.
;
# END OF CIF
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
####################################################################### 
# 
# 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_B
_database_code_depnum_ccdc_archive 'CCDC 1058985'
_audit_update_record             
;
2015-04-10 deposited with the CCDC.
2016-01-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H22 P, C17 H14 N O3 S, C H2 Cl2'
_chemical_formula_sum            'C43 H38 Cl2 N O3 P S'
_chemical_formula_weight         750.67

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_Hall  'P 1 '
_symmetry_space_group_name_H-M   'P 1   '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'

_cell_length_a                   10.0089(4)
_cell_length_b                   10.4658(4)
_cell_length_c                   10.8995(4)
_cell_angle_alpha                61.537(2)
_cell_angle_beta                 78.686(2)
_cell_angle_gamma                66.103(2)
_cell_volume                     917.68(6)
_cell_formula_units_Z            1
_cell_measurement_temperature    90.0(5)
_cell_measurement_reflns_used    7222
_cell_measurement_theta_min      3.08
_cell_measurement_theta_max      34.93

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             392
_exptl_absorpt_coefficient_mu    0.320
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8625
_exptl_absorpt_correction_T_max  0.9596
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      90.0(5)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'TRIUMPH curved graphite'
_diffrn_measurement_device_type  'Bruker Kappa APEX-II DUO'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14763
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_av_sigmaI/netI    0.0446
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.13
_diffrn_reflns_theta_max         35.01
_reflns_number_total             12497
_reflns_number_gt                11156
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0595P)²+0.1456P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details '4745 Friedel pairs (Flack, 1983) '
_refine_ls_abs_structure_Flack   0.03(4)
_refine_ls_number_reflns         12497
_refine_ls_number_parameters     465
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0412
_refine_ls_wR_factor_ref         0.1064
_refine_ls_wR_factor_gt          0.1001
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.83760(4) 0.59173(4) 0.87007(4) 0.01277(7) Uani 1 1 d . . .
O1 O 0.78802(16) 0.60745(17) 0.99882(15) 0.0206(3) Uani 1 1 d . . .
O2 O 0.99309(14) 0.50296(16) 0.86840(16) 0.0188(3) Uani 1 1 d . . .
O3 O 0.79063(15) 0.74191(15) 0.74704(15) 0.0177(2) Uani 1 1 d . . .
N1 N 0.56091(17) -0.01245(17) 0.80670(18) 0.0162(3) Uani 1 1 d . . .
H1N H 0.627(3) -0.092(3) 0.792(3) 0.019 Uiso 1 1 d . . .
C1 C 0.74749(18) 0.48149(19) 0.86065(18) 0.0126(3) Uani 1 1 d . . .
C2 C 0.59492(18) 0.54883(19) 0.83396(19) 0.0140(3) Uani 1 1 d . . .
H2 H 0.5406 0.6517 0.8238 0.017 Uiso 1 1 calc R . .
C3 C 0.52632(18) 0.46436(19) 0.82293(19) 0.0136(3) Uani 1 1 d . . .
H3 H 0.4242 0.5097 0.8059 0.016 Uiso 1 1 calc R . .
C4 C 0.60502(17) 0.31053(18) 0.83654(18) 0.0116(3) Uani 1 1 d . . .
C5 C 0.53737(18) 0.22511(19) 0.81808(19) 0.0131(3) Uani 1 1 d . . .
H5 H 0.4358 0.2700 0.7986 0.016 Uiso 1 1 calc R . .
C6 C 0.61713(18) 0.07755(19) 0.82797(19) 0.0130(3) Uani 1 1 d . . .
C7 C 0.76921(18) 0.00961(19) 0.8615(2) 0.0153(3) Uani 1 1 d . . .
H7 H 0.8242 -0.0931 0.8715 0.018 Uiso 1 1 calc R . .
C8 C 0.83662(19) 0.0901(2) 0.8791(2) 0.0151(3) Uani 1 1 d . . .
H8 H 0.9379 0.0428 0.9005 0.018 Uiso 1 1 calc R . .
C9 C 0.75750(17) 0.24385(18) 0.86604(18) 0.0122(3) Uani 1 1 d . . .
C10 C 0.82606(18) 0.33199(19) 0.87776(19) 0.0131(3) Uani 1 1 d . . .
H10 H 0.9275 0.2873 0.8977 0.016 Uiso 1 1 calc R . .
C11 C 0.43318(19) 0.0517(2) 0.72745(19) 0.0153(3) Uani 1 1 d . . .
C12 C 0.2955(2) 0.1275(2) 0.7684(2) 0.0172(3) Uani 1 1 d . . .
H12 H 0.2840 0.1375 0.8523 0.021 Uiso 1 1 calc R . .
C13 C 0.1742(2) 0.1887(2) 0.6852(2) 0.0189(3) Uani 1 1 d . . .
H13 H 0.0807 0.2407 0.7137 0.023 Uiso 1 1 calc R . .
C14 C 0.1864(2) 0.1758(2) 0.5622(2) 0.0191(3) Uani 1 1 d . . .
C15 C 0.3243(2) 0.0961(2) 0.5239(2) 0.0198(3) Uani 1 1 d . . .
H15 H 0.3352 0.0848 0.4406 0.024 Uiso 1 1 calc R . .
C16 C 0.44631(19) 0.0330(2) 0.6063(2) 0.0181(3) Uani 1 1 d . . .
H16 H 0.5390 -0.0231 0.5799 0.022 Uiso 1 1 calc R . .
C17 C 0.0537(2) 0.2451(3) 0.4733(3) 0.0309(5) Uani 1 1 d . . .
H17A H -0.0329 0.2417 0.5332 0.046 Uiso 1 1 calc R . .
H17B H 0.0678 0.1851 0.4219 0.046 Uiso 1 1 calc R . .
H17C H 0.0401 0.3536 0.4070 0.046 Uiso 1 1 calc R . .
P1 P 0.55548(4) 0.59409(5) 0.31980(4) 0.01213(8) Uani 1 1 d . . .
C18 C 0.47185(18) 0.7239(2) 0.14828(19) 0.0144(3) Uani 1 1 d . . .
H18A H 0.5491 0.7413 0.0769 0.017 Uiso 1 1 calc R . .
H18B H 0.4196 0.6742 0.1270 0.017 Uiso 1 1 calc R . .
C19 C 0.36576(19) 0.8788(2) 0.14166(19) 0.0147(3) Uani 1 1 d . . .
C20 C 0.2162(2) 0.9059(2) 0.1570(2) 0.0201(3) Uani 1 1 d . . .
H20 H 0.1824 0.8277 0.1694 0.024 Uiso 1 1 calc R . .
C21 C 0.1163(2) 1.0456(3) 0.1542(2) 0.0270(4) Uani 1 1 d . . .
H21 H 0.0149 1.0629 0.1638 0.032 Uiso 1 1 calc R . .
C22 C 0.1643(3) 1.1601(3) 0.1376(2) 0.0289(4) Uani 1 1 d . . .
H22 H 0.0960 1.2555 0.1365 0.035 Uiso 1 1 calc R . .
C23 C 0.3125(3) 1.1348(2) 0.1225(2) 0.0246(4) Uani 1 1 d . . .
H23 H 0.3455 1.2133 0.1106 0.029 Uiso 1 1 calc R . .
C24 C 0.4138(2) 0.9940(2) 0.1249(2) 0.0177(3) Uani 1 1 d . . .
H24 H 0.5152 0.9771 0.1151 0.021 Uiso 1 1 calc R . .
C25 C 0.63017(18) 0.39715(19) 0.34169(19) 0.0143(3) Uani 1 1 d . . .
C26 C 0.6890(2) 0.2767(2) 0.4714(2) 0.0182(3) Uani 1 1 d . . .
H26 H 0.6847 0.2995 0.5469 0.022 Uiso 1 1 calc R . .
C27 C 0.7535(2) 0.1242(2) 0.4893(2) 0.0217(4) Uani 1 1 d . . .
H27 H 0.7945 0.0423 0.5768 0.026 Uiso 1 1 calc R . .
C28 C 0.7580(2) 0.0913(2) 0.3791(3) 0.0249(4) Uani 1 1 d . . .
H28 H 0.8014 -0.0134 0.3918 0.030 Uiso 1 1 calc R . .
C29 C 0.7000(2) 0.2098(2) 0.2510(2) 0.0239(4) Uani 1 1 d . . .
H29 H 0.7035 0.1861 0.1762 0.029 Uiso 1 1 calc R . .
C30 C 0.6364(2) 0.3637(2) 0.2311(2) 0.0185(3) Uani 1 1 d . . .
H30 H 0.5977 0.4453 0.1426 0.022 Uiso 1 1 calc R . .
C31 C 0.69767(18) 0.64690(19) 0.33839(18) 0.0131(3) Uani 1 1 d . . .
C32 C 0.77631(19) 0.7150(2) 0.22135(19) 0.0160(3) Uani 1 1 d . . .
H32 H 0.7515 0.7383 0.1313 0.019 Uiso 1 1 calc R . .
C33 C 0.8911(2) 0.7488(2) 0.2369(2) 0.0176(3) Uani 1 1 d . . .
H33 H 0.9435 0.7970 0.1572 0.021 Uiso 1 1 calc R . .
C34 C 0.9290(2) 0.7121(2) 0.3685(2) 0.0185(3) Uani 1 1 d . . .
H34 H 1.0082 0.7341 0.3788 0.022 Uiso 1 1 calc R . .
C35 C 0.8516(2) 0.6434(2) 0.4855(2) 0.0192(3) Uani 1 1 d . . .
H35 H 0.8785 0.6181 0.5754 0.023 Uiso 1 1 calc R . .
C36 C 0.7352(2) 0.6114(2) 0.47126(19) 0.0169(3) Uani 1 1 d . . .
H36 H 0.6813 0.5659 0.5510 0.020 Uiso 1 1 calc R . .
C37 C 0.41598(18) 0.61482(19) 0.44767(18) 0.0132(3) Uani 1 1 d . . .
C38 C 0.33686(19) 0.5147(2) 0.50774(19) 0.0152(3) Uani 1 1 d . . .
H38 H 0.3647 0.4265 0.4906 0.018 Uiso 1 1 calc R . .
C39 C 0.21690(19) 0.5461(2) 0.5929(2) 0.0168(3) Uani 1 1 d . . .
H39 H 0.1650 0.4768 0.6366 0.020 Uiso 1 1 calc R . .
C40 C 0.1726(2) 0.6786(2) 0.6146(2) 0.0172(3) Uani 1 1 d . . .
H40 H 0.0885 0.7015 0.6697 0.021 Uiso 1 1 calc R . .
C41 C 0.2520(2) 0.7772(2) 0.5552(2) 0.0173(3) Uani 1 1 d . . .
H41 H 0.2230 0.8663 0.5715 0.021 Uiso 1 1 calc R . .
C42 C 0.37327(19) 0.7458(2) 0.4724(2) 0.0163(3) Uani 1 1 d . . .
H42 H 0.4274 0.8131 0.4325 0.020 Uiso 1 1 calc R . .
C43 C 0.1555(2) 0.5756(3) 1.0242(3) 0.0297(5) Uani 1 1 d . . .
H43A H 0.0501 0.5962 1.0452 0.036 Uiso 1 1 calc R . .
H43B H 0.1889 0.5091 0.9750 0.036 Uiso 1 1 calc R . .
Cl1 Cl 0.25316(6) 0.47669(6) 1.18138(7) 0.03190(12) Uani 1 1 d . . .
Cl2 Cl 0.18201(7) 0.75500(6) 0.91436(6) 0.03241(12) 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
S1 O2 1.4557(13) . ?
S1 O1 1.4572(14) . ?
S1 O3 1.4593(14) . ?
S1 C1 1.7741(16) . ?
N1 C6 1.395(2) . ?
N1 C11 1.420(2) . ?
N1 H1N 0.89(3) . ?
C1 C10 1.373(2) . ?
C1 C2 1.421(2) . ?
C2 C3 1.376(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.423(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.419(2) . ?
C4 C9 1.427(2) . ?
C5 C6 1.382(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.432(2) . ?
C7 C8 1.367(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.425(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.413(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.392(3) . ?
C11 C16 1.399(3) . ?
C12 C13 1.398(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.388(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.396(3) . ?
C14 C17 1.511(3) . ?
C15 C16 1.395(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
P1 C25 1.7936(17) . ?
P1 C37 1.7939(17) . ?
P1 C31 1.7969(16) . ?
P1 C18 1.8202(18) . ?
C18 C19 1.511(2) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C24 1.394(2) . ?
C19 C20 1.398(2) . ?
C20 C21 1.387(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.388(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.387(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.401(3) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 C30 1.391(3) . ?
C25 C26 1.400(3) . ?
C26 C27 1.386(3) . ?
C26 H26 0.9500 . ?
C27 C28 1.386(3) . ?
C27 H27 0.9500 . ?
C28 C29 1.382(3) . ?
C28 H28 0.9500 . ?
C29 C30 1.392(3) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
C31 C32 1.396(3) . ?
C31 C36 1.401(2) . ?
C32 C33 1.391(2) . ?
C32 H32 0.9500 . ?
C33 C34 1.386(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.390(3) . ?
C34 H34 0.9500 . ?
C35 C36 1.389(2) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C37 C38 1.403(2) . ?
C37 C42 1.403(2) . ?
C38 C39 1.395(3) . ?
C38 H38 0.9500 . ?
C39 C40 1.395(3) . ?
C39 H39 0.9500 . ?
C40 C41 1.394(3) . ?
C40 H40 0.9500 . ?
C41 C42 1.387(3) . ?
C41 H41 0.9500 . ?
C42 H42 0.9500 . ?
C43 Cl1 1.763(2) . ?
C43 Cl2 1.779(3) . ?
C43 H43A 0.9900 . ?
C43 H43B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 113.71(9) . . ?
O2 S1 O3 112.92(8) . . ?
O1 S1 O3 111.81(8) . . ?
O2 S1 C1 105.51(8) . . ?
O1 S1 C1 106.46(8) . . ?
O3 S1 C1 105.67(8) . . ?
C6 N1 C11 123.35(14) . . ?
C6 N1 H1N 115.7(17) . . ?
C11 N1 H1N 110.1(17) . . ?
C10 C1 C2 120.38(14) . . ?
C10 C1 S1 119.69(12) . . ?
C2 C1 S1 119.93(12) . . ?
C3 C2 C1 119.69(15) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 121.45(15) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C5 C4 C3 122.09(14) . . ?
C5 C4 C9 119.88(14) . . ?
C3 C4 C9 118.00(13) . . ?
C6 C5 C4 120.97(15) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 N1 124.85(15) . . ?
C5 C6 C7 118.85(14) . . ?
N1 C6 C7 116.30(14) . . ?
C8 C7 C6 121.09(15) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C7 C8 C9 121.06(15) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
C10 C9 C8 122.10(14) . . ?
C10 C9 C4 119.78(14) . . ?
C8 C9 C4 118.10(14) . . ?
C1 C10 C9 120.66(15) . . ?
C1 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C12 C11 C16 119.07(16) . . ?
C12 C11 N1 122.47(16) . . ?
C16 C11 N1 118.42(16) . . ?
C11 C12 C13 119.62(17) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C14 C13 C12 121.91(17) . . ?
C14 C13 H13 119.0 . . ?
C12 C13 H13 119.0 . . ?
C13 C14 C15 118.04(17) . . ?
C13 C14 C17 120.76(18) . . ?
C15 C14 C17 121.20(18) . . ?
C16 C15 C14 120.84(18) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C15 C16 C11 120.45(17) . . ?
C15 C16 H16 119.8 . . ?
C11 C16 H16 119.8 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C25 P1 C37 110.61(8) . . ?
C25 P1 C31 109.72(8) . . ?
C37 P1 C31 109.02(8) . . ?
C25 P1 C18 109.39(8) . . ?
C37 P1 C18 107.68(8) . . ?
C31 P1 C18 110.40(8) . . ?
C19 C18 P1 111.36(12) . . ?
C19 C18 H18A 109.4 . . ?
P1 C18 H18A 109.4 . . ?
C19 C18 H18B 109.4 . . ?
P1 C18 H18B 109.4 . . ?
H18A C18 H18B 108.0 . . ?
C24 C19 C20 118.97(16) . . ?
C24 C19 C18 121.56(15) . . ?
C20 C19 C18 119.44(15) . . ?
C21 C20 C19 120.80(19) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C20 C21 C22 120.2(2) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C23 C22 C21 119.69(19) . . ?
C23 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
C22 C23 C24 120.40(19) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 H23 119.8 . . ?
C19 C24 C23 119.97(18) . . ?
C19 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C30 C25 C26 120.05(16) . . ?
C30 C25 P1 121.21(14) . . ?
C26 C25 P1 118.68(13) . . ?
C27 C26 C25 119.87(18) . . ?
C27 C26 H26 120.1 . . ?
C25 C26 H26 120.1 . . ?
C28 C27 C26 119.85(19) . . ?
C28 C27 H27 120.1 . . ?
C26 C27 H27 120.1 . . ?
C29 C28 C27 120.48(18) . . ?
C29 C28 H28 119.8 . . ?
C27 C28 H28 119.8 . . ?
C28 C29 C30 120.28(19) . . ?
C28 C29 H29 119.9 . . ?
C30 C29 H29 119.9 . . ?
C25 C30 C29 119.46(18) . . ?
C25 C30 H30 120.3 . . ?
C29 C30 H30 120.3 . . ?
C32 C31 C36 120.03(15) . . ?
C32 C31 P1 119.91(13) . . ?
C36 C31 P1 119.95(13) . . ?
C33 C32 C31 119.84(16) . . ?
C33 C32 H32 120.1 . . ?
C31 C32 H32 120.1 . . ?
C34 C33 C32 120.04(17) . . ?
C34 C33 H33 120.0 . . ?
C32 C33 H33 120.0 . . ?
C33 C34 C35 120.34(16) . . ?
C33 C34 H34 119.8 . . ?
C35 C34 H34 119.8 . . ?
C36 C35 C34 120.22(17) . . ?
C36 C35 H35 119.9 . . ?
C34 C35 H35 119.9 . . ?
C35 C36 C31 119.51(17) . . ?
C35 C36 H36 120.2 . . ?
C31 C36 H36 120.2 . . ?
C38 C37 C42 119.97(16) . . ?
C38 C37 P1 120.83(13) . . ?
C42 C37 P1 118.61(13) . . ?
C39 C38 C37 119.35(16) . . ?
C39 C38 H38 120.3 . . ?
C37 C38 H38 120.3 . . ?
C40 C39 C38 120.50(16) . . ?
C40 C39 H39 119.7 . . ?
C38 C39 H39 119.7 . . ?
C41 C40 C39 119.88(17) . . ?
C41 C40 H40 120.1 . . ?
C39 C40 H40 120.1 . . ?
C42 C41 C40 120.23(16) . . ?
C42 C41 H41 119.9 . . ?
C40 C41 H41 119.9 . . ?
C41 C42 C37 120.02(16) . . ?
C41 C42 H42 120.0 . . ?
C37 C42 H42 120.0 . . ?
Cl1 C43 Cl2 110.92(11) . . ?
Cl1 C43 H43A 109.5 . . ?
Cl2 C43 H43A 109.5 . . ?
Cl1 C43 H43B 109.5 . . ?
Cl2 C43 H43B 109.5 . . ?
H43A C43 H43B 108.0 . . ?

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 H1N O3 0.89(3) 2.04(3) 2.922(2) 174(3) 1_545

_diffrn_measured_fraction_theta_max 0.959
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.665
_refine_diff_density_min         -0.539
_refine_diff_density_rms         0.078
# END OF CIF

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane/chloroform'
####################################################################### 
# 
# 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_A
_database_code_depnum_ccdc_archive 'CCDC 1058986'
_audit_update_record             
;
2015-04-10 deposited with the CCDC.
2016-01-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H36 P, C17 H14 N O3 S'
_chemical_formula_sum            'C33 H50 N O3 P S'
_chemical_formula_weight         571.77

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

_cell_length_a                   10.3977(4)
_cell_length_b                   18.2132(7)
_cell_length_c                   17.4211(6)
_cell_angle_alpha                90
_cell_angle_beta                 102.071(3)
_cell_angle_gamma                90
_cell_volume                     3226.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    90.0(5)
_cell_measurement_reflns_used    2479
_cell_measurement_theta_min      3.55
_cell_measurement_theta_max      49.53

_exptl_crystal_description       fragment
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.177
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1240
_exptl_absorpt_coefficient_mu    1.604
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7717
_exptl_absorpt_correction_T_max  0.9386
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      90.0(5)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'I\mS microfocus'
_diffrn_radiation_monochromator  'QUAZAR multilayer optics'
_diffrn_measurement_device_type  'Bruker Kappa APEX-II DUO'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14480
_diffrn_reflns_av_R_equivalents  0.0681
_diffrn_reflns_av_sigmaI/netI    0.0889
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.55
_diffrn_reflns_theta_max         59.04
_reflns_number_total             4636
_reflns_number_gt                2612
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0803P)²+1.8620P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4636
_refine_ls_number_parameters     359
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1341
_refine_ls_R_factor_gt           0.0702
_refine_ls_wR_factor_ref         0.1902
_refine_ls_wR_factor_gt          0.1605
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 1.37337(12) 0.22187(8) 0.90514(8) 0.0561(4) Uani 1 1 d . . .
O1 O 1.4426(3) 0.15529(19) 0.9342(2) 0.0644(10) Uani 1 1 d . . .
O2 O 1.3702(3) 0.2752(2) 0.9661(2) 0.0722(11) Uani 1 1 d . . .
O3 O 1.4190(3) 0.2506(2) 0.8382(2) 0.0750(11) Uani 1 1 d . . .
N1 N 0.5917(4) 0.1180(2) 0.8043(3) 0.0628(12) Uani 1 1 d D . .
H1N H 0.547(5) 0.133(3) 0.838(2) 0.075 Uiso 1 1 d D . .
C1 C 1.2085(5) 0.1948(3) 0.8696(3) 0.0491(13) Uani 1 1 d . . .
C2 C 1.1828(5) 0.1372(3) 0.8151(3) 0.0601(15) Uani 1 1 d . . .
H2 H 1.2532 0.1165 0.7952 0.072 Uiso 1 1 calc R . .
C3 C 1.0587(5) 0.1103(3) 0.7899(3) 0.0577(14) Uani 1 1 d . . .
H3 H 1.0440 0.0708 0.7536 0.069 Uiso 1 1 calc R . .
C4 C 0.9502(5) 0.1412(3) 0.8179(3) 0.0535(13) Uani 1 1 d . . .
C5 C 0.8213(5) 0.1133(3) 0.7940(3) 0.0549(14) Uani 1 1 d . . .
H5 H 0.8049 0.0737 0.7578 0.066 Uiso 1 1 calc R . .
C6 C 0.7193(5) 0.1433(3) 0.8228(3) 0.0534(13) Uani 1 1 d . . .
C7 C 0.7457(5) 0.2023(3) 0.8769(3) 0.0533(13) Uani 1 1 d . . .
H7 H 0.6760 0.2233 0.8971 0.064 Uiso 1 1 calc R . .
C8 C 0.8696(5) 0.2290(3) 0.9002(3) 0.0542(13) Uani 1 1 d . . .
H8 H 0.8848 0.2683 0.9367 0.065 Uiso 1 1 calc R . .
C9 C 0.9763(5) 0.2001(3) 0.8717(3) 0.0497(13) Uani 1 1 d . . .
C10 C 1.1063(5) 0.2255(3) 0.8967(3) 0.0513(13) Uani 1 1 d . . .
H10 H 1.1234 0.2649 0.9331 0.062 Uiso 1 1 calc R . .
C11 C 0.5357(5) 0.0681(3) 0.7462(3) 0.0580(14) Uani 1 1 d . . .
C12 C 0.5696(5) 0.0638(3) 0.6736(3) 0.0646(15) Uani 1 1 d . . .
H12 H 0.6343 0.0962 0.6616 0.078 Uiso 1 1 calc R . .
C13 C 0.5106(6) 0.0129(3) 0.6182(3) 0.0703(16) Uani 1 1 d . . .
H13 H 0.5364 0.0110 0.5690 0.084 Uiso 1 1 calc R . .
C14 C 0.4153(5) -0.0352(3) 0.6321(3) 0.0631(15) Uani 1 1 d . . .
C15 C 0.3783(5) -0.0284(3) 0.7041(3) 0.0627(15) Uani 1 1 d . . .
H15 H 0.3098 -0.0588 0.7146 0.075 Uiso 1 1 calc R . .
C16 C 0.4369(5) 0.0205(3) 0.7602(3) 0.0606(15) Uani 1 1 d . . .
H16 H 0.4105 0.0222 0.8091 0.073 Uiso 1 1 calc R . .
C17 C 0.3560(6) -0.0920(3) 0.5718(3) 0.0820(18) Uani 1 1 d . . .
H17A H 0.3071 -0.0673 0.5247 0.123 Uiso 1 1 calc R . .
H17B H 0.2961 -0.1236 0.5936 0.123 Uiso 1 1 calc R . .
H17C H 0.4262 -0.1219 0.5581 0.123 Uiso 1 1 calc R . .
C18 C 0.2969(5) 0.3780(3) 0.7329(3) 0.0583(14) Uani 1 1 d . . .
H18A H 0.3541 0.3529 0.7778 0.070 Uiso 1 1 calc R . .
H18B H 0.3261 0.4297 0.7334 0.070 Uiso 1 1 calc R . .
P1 P 0.32067(14) 0.33612(8) 0.64439(8) 0.0574(4) Uani 1 1 d . . .
C19 C 0.1549(5) 0.3766(3) 0.7454(3) 0.0618(15) Uani 1 1 d . . .
H19A H 0.0973 0.4028 0.7015 0.074 Uiso 1 1 calc R . .
H19B H 0.1245 0.3250 0.7445 0.074 Uiso 1 1 calc R . .
C20 C 0.1420(5) 0.4117(3) 0.8221(3) 0.0631(15) Uani 1 1 d . . .
H20A H 0.1753 0.4628 0.8238 0.076 Uiso 1 1 calc R . .
H20B H 0.1969 0.3844 0.8662 0.076 Uiso 1 1 calc R . .
C21 C 0.0009(5) 0.4123(3) 0.8320(3) 0.0743(17) Uani 1 1 d . . .
H21A H -0.0525 0.4423 0.7905 0.111 Uiso 1 1 calc R . .
H21B H -0.0030 0.4331 0.8833 0.111 Uiso 1 1 calc R . .
H21C H -0.0332 0.3620 0.8285 0.111 Uiso 1 1 calc R . .
C22 C 0.2801(5) 0.2396(3) 0.6374(3) 0.0642(15) Uani 1 1 d . . .
H22A H 0.3263 0.2177 0.5987 0.077 Uiso 1 1 calc R . .
H22B H 0.3180 0.2171 0.6888 0.077 Uiso 1 1 calc R . .
C23 C 0.1382(5) 0.2162(3) 0.6151(3) 0.0664(15) Uani 1 1 d . . .
H23A H 0.0921 0.2461 0.5703 0.080 Uiso 1 1 calc R . .
H23B H 0.0950 0.2246 0.6598 0.080 Uiso 1 1 calc R . .
C24 C 0.1284(6) 0.1345(3) 0.5924(3) 0.0728(16) Uani 1 1 d . . .
H24A H 0.1777 0.1050 0.6366 0.087 Uiso 1 1 calc R . .
H24B H 0.1693 0.1267 0.5466 0.087 Uiso 1 1 calc R . .
C25 C -0.0163(6) 0.1081(3) 0.5720(4) 0.0857(19) Uani 1 1 d . . .
H25A H -0.0583 0.1178 0.6163 0.128 Uiso 1 1 calc R . .
H25B H -0.0186 0.0552 0.5611 0.128 Uiso 1 1 calc R . .
H25C H -0.0636 0.1344 0.5255 0.128 Uiso 1 1 calc R . .
C26 C 0.4898(5) 0.3417(3) 0.6371(3) 0.0645(15) Uani 1 1 d . . .
H26A H 0.4958 0.3293 0.5827 0.077 Uiso 1 1 calc R . .
H26B H 0.5190 0.3933 0.6467 0.077 Uiso 1 1 calc R . .
C27 C 0.5838(5) 0.2932(3) 0.6922(3) 0.0648(15) Uani 1 1 d . . .
H27A H 0.5537 0.2417 0.6847 0.078 Uiso 1 1 calc R . .
H27B H 0.5829 0.3073 0.7470 0.078 Uiso 1 1 calc R . .
C28 C 0.7240(5) 0.2985(3) 0.6794(3) 0.0673(16) Uani 1 1 d . . .
H28A H 0.7513 0.3507 0.6835 0.081 Uiso 1 1 calc R . .
H28B H 0.7829 0.2714 0.7221 0.081 Uiso 1 1 calc R . .
C29 C 0.7431(6) 0.2686(3) 0.6012(3) 0.0859(19) Uani 1 1 d . . .
H29A H 0.7195 0.2165 0.5973 0.129 Uiso 1 1 calc R . .
H29B H 0.8353 0.2745 0.5975 0.129 Uiso 1 1 calc R . .
H29C H 0.6867 0.2957 0.5584 0.129 Uiso 1 1 calc R . .
C30 C 0.2282(5) 0.3853(3) 0.5628(3) 0.0661(15) Uani 1 1 d . . .
H30A H 0.2558 0.3686 0.5146 0.079 Uiso 1 1 calc R . .
H30B H 0.1341 0.3726 0.5572 0.079 Uiso 1 1 calc R . .
C31 C 0.2421(7) 0.4677(3) 0.5682(4) 0.093(2) Uani 1 1 d . . .
H31A H 0.3370 0.4798 0.5814 0.112 Uiso 1 1 calc R . .
H31B H 0.2032 0.4848 0.6123 0.112 Uiso 1 1 calc R . .
C32 C 0.1719(9) 0.5161(7) 0.4866(6) 0.181(6) Uani 1 1 d . . .
H32A H 0.1007 0.4887 0.4515 0.217 Uiso 1 1 calc R . .
H32B H 0.1404 0.5651 0.4988 0.217 Uiso 1 1 calc R . .
C33 C 0.2806(13) 0.5189(6) 0.4599(7) 0.212(6) Uani 1 1 d . . .
H33A H 0.2640 0.5448 0.4095 0.318 Uiso 1 1 calc R . .
H33B H 0.3108 0.4689 0.4527 0.318 Uiso 1 1 calc R . .
H33C H 0.3482 0.5450 0.4976 0.318 Uiso 1 1 calc R . .


_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 O2 1.445(4) . ?
S1 O3 1.446(3) . ?
S1 O1 1.446(3) . ?
S1 C1 1.767(5) . ?
N1 C6 1.377(6) . ?
N1 C11 1.395(7) . ?
N1 H1N 0.868(19) . ?
C1 C10 1.369(6) . ?
C1 C2 1.403(7) . ?
C2 C3 1.364(7) . ?
C2 H2 0.9500 . ?
C3 C4 1.434(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.412(7) . ?
C4 C9 1.412(7) . ?
C5 C6 1.377(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.417(6) . ?
C7 C8 1.357(7) . ?
C7 H7 0.9500 . ?
C8 C9 1.409(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.410(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.384(7) . ?
C11 C16 1.403(7) . ?
C12 C13 1.386(7) . ?
C12 H12 0.9500 . ?
C13 C14 1.381(7) . ?
C13 H13 0.9500 . ?
C14 C15 1.392(7) . ?
C14 C17 1.511(7) . ?
C15 C16 1.367(7) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.537(7) . ?
C18 P1 1.783(5) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
P1 C30 1.783(5) . ?
P1 C26 1.792(5) . ?
P1 C22 1.806(5) . ?
C19 C20 1.513(6) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.513(7) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.506(7) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.537(7) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.549(7) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 C27 1.505(7) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C28 1.524(7) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 C29 1.518(7) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 C31 1.509(7) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 C32 1.702(12) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 C33 1.309(14) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O3 114.3(2) . . ?
O2 S1 O1 113.1(2) . . ?
O3 S1 O1 111.2(2) . . ?
O2 S1 C1 106.0(2) . . ?
O3 S1 C1 106.0(2) . . ?
O1 S1 C1 105.3(2) . . ?
C6 N1 C11 128.6(4) . . ?
C6 N1 H1N 112(4) . . ?
C11 N1 H1N 119(4) . . ?
C10 C1 C2 119.2(5) . . ?
C10 C1 S1 122.1(4) . . ?
C2 C1 S1 118.7(4) . . ?
C3 C2 C1 121.3(5) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C2 C3 C4 120.6(5) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C9 120.5(4) . . ?
C5 C4 C3 121.6(5) . . ?
C9 C4 C3 117.9(5) . . ?
C6 C5 C4 120.4(5) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
N1 C6 C5 124.1(5) . . ?
N1 C6 C7 116.9(5) . . ?
C5 C6 C7 119.0(5) . . ?
C8 C7 C6 120.7(5) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C9 121.9(5) . . ?
C7 C8 H8 119.0 . . ?
C9 C8 H8 119.0 . . ?
C8 C9 C10 122.9(5) . . ?
C8 C9 C4 117.5(5) . . ?
C10 C9 C4 119.6(4) . . ?
C1 C10 C9 121.5(5) . . ?
C1 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C12 C11 N1 123.5(5) . . ?
C12 C11 C16 117.3(5) . . ?
N1 C11 C16 119.1(5) . . ?
C11 C12 C13 120.9(5) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C14 C13 C12 122.1(6) . . ?
C14 C13 H13 119.0 . . ?
C12 C13 H13 119.0 . . ?
C13 C14 C15 116.5(5) . . ?
C13 C14 C17 121.0(5) . . ?
C15 C14 C17 122.5(5) . . ?
C16 C15 C14 122.4(5) . . ?
C16 C15 H15 118.8 . . ?
C14 C15 H15 118.8 . . ?
C15 C16 C11 120.8(5) . . ?
C15 C16 H16 119.6 . . ?
C11 C16 H16 119.6 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 P1 115.2(4) . . ?
C19 C18 H18A 108.5 . . ?
P1 C18 H18A 108.5 . . ?
C19 C18 H18B 108.5 . . ?
P1 C18 H18B 108.5 . . ?
H18A C18 H18B 107.5 . . ?
C18 P1 C30 109.0(2) . . ?
C18 P1 C26 110.6(2) . . ?
C30 P1 C26 106.8(3) . . ?
C18 P1 C22 113.7(3) . . ?
C30 P1 C22 110.8(3) . . ?
C26 P1 C22 105.6(2) . . ?
C20 C19 C18 112.5(4) . . ?
C20 C19 H19A 109.1 . . ?
C18 C19 H19A 109.1 . . ?
C20 C19 H19B 109.1 . . ?
C18 C19 H19B 109.1 . . ?
H19A C19 H19B 107.8 . . ?
C19 C20 C21 111.8(5) . . ?
C19 C20 H20A 109.3 . . ?
C21 C20 H20A 109.3 . . ?
C19 C20 H20B 109.3 . . ?
C21 C20 H20B 109.3 . . ?
H20A C20 H20B 107.9 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 P1 119.7(4) . . ?
C23 C22 H22A 107.4 . . ?
P1 C22 H22A 107.4 . . ?
C23 C22 H22B 107.4 . . ?
P1 C22 H22B 107.4 . . ?
H22A C22 H22B 106.9 . . ?
C22 C23 C24 110.4(4) . . ?
C22 C23 H23A 109.6 . . ?
C24 C23 H23A 109.6 . . ?
C22 C23 H23B 109.6 . . ?
C24 C23 H23B 109.6 . . ?
H23A C23 H23B 108.1 . . ?
C23 C24 C25 111.7(5) . . ?
C23 C24 H24A 109.3 . . ?
C25 C24 H24A 109.3 . . ?
C23 C24 H24B 109.3 . . ?
C25 C24 H24B 109.3 . . ?
H24A C24 H24B 107.9 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C27 C26 P1 116.0(4) . . ?
C27 C26 H26A 108.3 . . ?
P1 C26 H26A 108.3 . . ?
C27 C26 H26B 108.3 . . ?
P1 C26 H26B 108.3 . . ?
H26A C26 H26B 107.4 . . ?
C26 C27 C28 112.5(4) . . ?
C26 C27 H27A 109.1 . . ?
C28 C27 H27A 109.1 . . ?
C26 C27 H27B 109.1 . . ?
C28 C27 H27B 109.1 . . ?
H27A C27 H27B 107.8 . . ?
C29 C28 C27 114.7(5) . . ?
C29 C28 H28A 108.6 . . ?
C27 C28 H28A 108.6 . . ?
C29 C28 H28B 108.6 . . ?
C27 C28 H28B 108.6 . . ?
H28A C28 H28B 107.6 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C31 C30 P1 114.9(4) . . ?
C31 C30 H30A 108.5 . . ?
P1 C30 H30A 108.5 . . ?
C31 C30 H30B 108.5 . . ?
P1 C30 H30B 108.5 . . ?
H30A C30 H30B 107.5 . . ?
C30 C31 C32 116.3(6) . . ?
C30 C31 H31A 108.2 . . ?
C32 C31 H31A 108.2 . . ?
C30 C31 H31B 108.2 . . ?
C32 C31 H31B 108.2 . . ?
H31A C31 H31B 107.4 . . ?
C33 C32 C31 93.8(9) . . ?
C33 C32 H32A 113.0 . . ?
C31 C32 H32A 113.0 . . ?
C33 C32 H32B 113.0 . . ?
C31 C32 H32B 113.0 . . ?
H32A C32 H32B 110.4 . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 S1 C1 C10 3.1(5) . . . . ?
O3 S1 C1 C10 -118.8(4) . . . . ?
O1 S1 C1 C10 123.2(4) . . . . ?
O2 S1 C1 C2 -173.4(4) . . . . ?
O3 S1 C1 C2 64.7(4) . . . . ?
O1 S1 C1 C2 -53.3(4) . . . . ?
C10 C1 C2 C3 -1.5(8) . . . . ?
S1 C1 C2 C3 175.1(4) . . . . ?
C1 C2 C3 C4 1.0(8) . . . . ?
C2 C3 C4 C5 -178.6(5) . . . . ?
C2 C3 C4 C9 0.2(7) . . . . ?
C9 C4 C5 C6 0.1(7) . . . . ?
C3 C4 C5 C6 178.9(5) . . . . ?
C11 N1 C6 C5 -11.2(9) . . . . ?
C11 N1 C6 C7 170.9(5) . . . . ?
C4 C5 C6 N1 -178.1(5) . . . . ?
C4 C5 C6 C7 -0.2(7) . . . . ?
N1 C6 C7 C8 178.0(5) . . . . ?
C5 C6 C7 C8 -0.1(8) . . . . ?
C6 C7 C8 C9 0.4(8) . . . . ?
C7 C8 C9 C10 -178.1(5) . . . . ?
C7 C8 C9 C4 -0.5(7) . . . . ?
C5 C4 C9 C8 0.2(7) . . . . ?
C3 C4 C9 C8 -178.6(4) . . . . ?
C5 C4 C9 C10 178.0(4) . . . . ?
C3 C4 C9 C10 -0.9(7) . . . . ?
C2 C1 C10 C9 0.7(7) . . . . ?
S1 C1 C10 C9 -175.7(4) . . . . ?
C8 C9 C10 C1 178.0(4) . . . . ?
C4 C9 C10 C1 0.4(7) . . . . ?
C6 N1 C11 C12 -35.8(8) . . . . ?
C6 N1 C11 C16 146.0(5) . . . . ?
N1 C11 C12 C13 180.0(5) . . . . ?
C16 C11 C12 C13 -1.8(8) . . . . ?
C11 C12 C13 C14 0.5(9) . . . . ?
C12 C13 C14 C15 2.0(8) . . . . ?
C12 C13 C14 C17 -177.8(5) . . . . ?
C13 C14 C15 C16 -3.2(8) . . . . ?
C17 C14 C15 C16 176.5(5) . . . . ?
C14 C15 C16 C11 2.0(8) . . . . ?
C12 C11 C16 C15 0.6(8) . . . . ?
N1 C11 C16 C15 178.9(5) . . . . ?
C19 C18 P1 C30 62.8(4) . . . . ?
C19 C18 P1 C26 179.9(4) . . . . ?
C19 C18 P1 C22 -61.5(4) . . . . ?
P1 C18 C19 C20 179.0(4) . . . . ?
C18 C19 C20 C21 177.9(4) . . . . ?
C18 P1 C22 C23 78.4(5) . . . . ?
C30 P1 C22 C23 -44.9(5) . . . . ?
C26 P1 C22 C23 -160.2(4) . . . . ?
P1 C22 C23 C24 165.6(4) . . . . ?
C22 C23 C24 C25 178.0(5) . . . . ?
C18 P1 C26 C27 71.6(5) . . . . ?
C30 P1 C26 C27 -169.9(4) . . . . ?
C22 P1 C26 C27 -51.9(5) . . . . ?
P1 C26 C27 C28 177.1(4) . . . . ?
C26 C27 C28 C29 -66.6(6) . . . . ?
C18 P1 C30 C31 46.7(5) . . . . ?
C26 P1 C30 C31 -72.8(5) . . . . ?
C22 P1 C30 C31 172.6(4) . . . . ?
P1 C30 C31 C32 172.2(4) . . . . ?
C30 C31 C32 C33 -94.2(10) . . . . ?

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 H1N O1 0.868(19) 2.21(2) 3.073(5) 172(5) 1_455

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        59.04
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.509
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.053
# END OF CIF
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
