# 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. 
# 
#######################################################################

data_emo270916
_database_code_depnum_ccdc_archive 'CCDC 1846730'
_audit_update_record             
;
2018-06-01 deposited with the CCDC.
2018-07-05 downloaded from the CCDC.
;

_audit_creation_date             2016-09-29T11:14:59-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C19 H29 O3 P S'
_chemical_formula_sum            'C19 H29 O3 P S'
_chemical_formula_weight         368.45
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a                   10.7191(5)
_cell_length_b                   13.3649(6)
_cell_length_c                   14.3514(7)
_cell_angle_alpha                90.835(2)
_cell_angle_beta                 100.446(2)
_cell_angle_gamma                110.079(2)
_cell_volume                     1892.43(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9910
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      30.28
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             792

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.27
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_absorpt_correction_T_min  0.715
_exptl_absorpt_correction_T_max  0.905

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'Bruker Kappa APEX II'
_diffrn_measurement_method       ω-φ
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_number            41652
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.087
_diffrn_reflns_theta_max         30.393
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.893
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.893
_diffrn_reflns_point_group_measured_fraction_max 0.893
_reflns_number_total             10212
_reflns_number_gt                9433
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_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-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0358P)²+0.8978P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         10212
_refine_ls_number_parameters     443
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0305
_refine_ls_R_factor_gt           0.0277
_refine_ls_wR_factor_ref         0.0767
_refine_ls_wR_factor_gt          0.0742
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.498
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.05

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.80192(2) 0.32630(2) 0.09778(2) 0.01247(5) Uani 1 d . .
S2 S 0.82730(2) 0.84023(2) 0.35296(2) 0.01178(5) Uani 1 d . .
P1 P 0.89804(2) 0.59092(2) 0.16034(2) 0.01097(5) Uani 1 d . .
P2 P 0.99541(2) 1.08768(2) 0.29844(2) 0.01109(6) Uani 1 d . .
O1 O 0.90533(8) 0.29439(7) 0.15638(6) 0.02127(16) Uani 1 d . .
O2 O 0.85843(8) 0.41714(6) 0.04403(5) 0.01764(15) Uani 1 d . .
O3 O 0.69232(8) 0.23827(6) 0.04179(6) 0.02216(17) Uani 1 d . .
O4 O 0.93223(8) 0.80059(6) 0.33427(5) 0.01717(15) Uani 1 d . .
O5 O 0.70910(8) 0.75722(6) 0.37344(6) 0.01885(15) Uani 1 d . .
O6 O 0.88087(7) 0.93472(6) 0.42046(5) 0.01405(14) Uani 1 d . .
C1 C 0.57826(10) 0.34228(8) 0.29130(7) 0.01522(19) Uani 1 d . .
H1 H 0.511768 0.292324 0.319453 0.018 Uiso 1 calc . .
C2 C 0.62997(10) 0.30597(8) 0.22131(7) 0.01439(18) Uani 1 d . .
H19 H 0.598094 0.231835 0.201632 0.017 Uiso 1 calc . .
C3 C 0.72838(10) 0.37774(8) 0.17977(7) 0.01202(17) Uani 1 d . .
C4 C 0.77176(9) 0.48739(8) 0.20687(7) 0.01130(17) Uani 1 d . .
C5 C 0.84812(10) 0.62689(8) 0.04077(7) 0.01297(17) Uani 1 d . .
H5 H 0.896031 0.601025 -0.0025 0.016 Uiso 1 calc . .
C6 C 0.69458(11) 0.57500(9) 0.00263(7) 0.01699(19) Uani 1 d . .
H7 H 0.666974 0.496298 0.002575 0.02 Uiso 1 calc . .
H6 H 0.644907 0.599584 0.044355 0.02 Uiso 1 calc . .
C7 C 0.65913(12) 0.60550(9) -0.09853(8) 0.0208(2) Uani 1 d . .
H13 H 0.702443 0.574971 -0.141058 0.025 Uiso 1 calc . .
H14 H 0.559796 0.574438 -0.121561 0.025 Uiso 1 calc . .
C8 C 0.70628(11) 0.72683(9) -0.10301(8) 0.0192(2) Uani 1 d . .
H2 H 0.688608 0.743437 -0.170058 0.023 Uiso 1 calc . .
H8 H 0.653727 0.756295 -0.067649 0.023 Uiso 1 calc . .
C9 C 1.34216(11) 0.66741(10) 0.30669(9) 0.0240(2) Uani 1 d . .
H3 H 1.435029 0.665488 0.323281 0.029 Uiso 1 calc . .
H28 H 1.336169 0.723539 0.349608 0.029 Uiso 1 calc . .
C10 C 1.31447(11) 0.69455(9) 0.20376(9) 0.0217(2) Uani 1 d . .
H27 H 1.329827 0.642399 0.161684 0.026 Uiso 1 calc . .
H26 H 1.378805 0.766461 0.197065 0.026 Uiso 1 calc . .
C11 C 1.16956(10) 0.69263(8) 0.17254(8) 0.01577(19) Uani 1 d . .
H25 H 1.153469 0.70578 0.104453 0.019 Uiso 1 calc . .
H4 H 1.157016 0.750334 0.20955 0.019 Uiso 1 calc . .
C12 C 1.06704(10) 0.58440(8) 0.18781(7) 0.01273(17) Uani 1 d . .
H24 H 1.072245 0.527321 0.144472 0.015 Uiso 1 calc . .
C13 C 0.85708(11) 0.77976(9) -0.06065(8) 0.0186(2) Uani 1 d . .
H9 H 0.8825 0.85837 -0.059892 0.022 Uiso 1 calc . .
H10 H 0.910125 0.757714 -0.101259 0.022 Uiso 1 calc . .
C14 C 0.89265(10) 0.74950(8) 0.04055(7) 0.01541(18) Uani 1 d . .
H12 H 0.846238 0.777004 0.082875 0.018 Uiso 1 calc . .
H11 H 0.991582 0.78221 0.064752 0.018 Uiso 1 calc . .
C15 C 0.62193(10) 0.45053(8) 0.32112(7) 0.01429(18) Uani 1 d . .
C16 C 0.71826(10) 0.52283(8) 0.27773(7) 0.01315(18) Uani 1 d . .
H15 H 0.747978 0.597079 0.296456 0.016 Uiso 1 calc . .
C17 C 0.56746(12) 0.48855(9) 0.39892(8) 0.0209(2) Uani 1 d . .
H17 H 0.469358 0.470338 0.378872 0.031 Uiso 1 calc . .
H18 H 0.611198 0.56623 0.411753 0.031 Uiso 1 calc . .
H16 H 0.586404 0.453825 0.45676 0.031 Uiso 1 calc . .
C18 C 1.09420(11) 0.55664(9) 0.29122(8) 0.0186(2) Uani 1 d . .
H22 H 1.079072 0.608584 0.333669 0.022 Uiso 1 calc . .
H23 H 1.030305 0.484524 0.297842 0.022 Uiso 1 calc . .
C19 C 1.23997(11) 0.55927(10) 0.32062(8) 0.0217(2) Uani 1 d . .
H21 H 1.256992 0.544679 0.388286 0.026 Uiso 1 calc . .
H20 H 1.252148 0.502417 0.282212 0.026 Uiso 1 calc . .
C20 C 0.61832(10) 0.86056(9) 0.09416(7) 0.01588(19) Uani 1 d . .
H29 H 0.537797 0.816661 0.052432 0.019 Uiso 1 calc . .
C21 C 0.69494(10) 0.95881(8) 0.06700(7) 0.01472(18) Uani 1 d . .
C22 C 0.80960(10) 1.02454(8) 0.13161(7) 0.01365(18) Uani 1 d . .
H53 H 0.860861 1.092753 0.114732 0.016 Uiso 1 calc . .
C23 C 0.85006(10) 0.99144(8) 0.22073(7) 0.01182(17) Uani 1 d . .
C24 C 1.13693(10) 1.04335(8) 0.34015(7) 0.01247(17) Uani 1 d . .
H43 H 1.108799 0.987196 0.38512 0.015 Uiso 1 calc . .
C25 C 1.25995(10) 1.13679(8) 0.39397(7) 0.01415(18) Uani 1 d . .
H45 H 1.28898 1.193952 0.351047 0.017 Uiso 1 calc . .
H46 H 1.234912 1.166908 0.448184 0.017 Uiso 1 calc . .
C26 C 1.37621(11) 1.09676(9) 0.43033(8) 0.0195(2) Uani 1 d . .
H48 H 1.456234 1.157554 0.462984 0.023 Uiso 1 calc . .
H47 H 1.348995 1.043994 0.477265 0.023 Uiso 1 calc . .
C27 C 1.41470(11) 1.04503(9) 0.34970(9) 0.0209(2) Uani 1 d . .
H30 H 1.452967 1.099947 0.306997 0.025 Uiso 1 calc . .
H49 H 1.485215 1.015435 0.376518 0.025 Uiso 1 calc . .
C28 C 0.65671(12) 0.99364(9) -0.03010(7) 0.0203(2) Uani 1 d . .
H31 H 0.718358 0.986163 -0.070257 0.03 Uiso 1 calc . .
H56 H 0.663414 1.068544 -0.024205 0.03 Uiso 1 calc . .
H55 H 0.563503 0.948877 -0.05902 0.03 Uiso 1 calc . .
C29 C 0.65859(10) 0.82603(8) 0.18195(7) 0.01467(18) Uani 1 d . .
H54 H 0.606406 0.758126 0.198867 0.018 Uiso 1 calc . .
C30 C 0.77414(10) 0.88991(8) 0.24480(7) 0.01186(17) Uani 1 d . .
C31 C 0.95919(10) 1.16339(8) 0.39014(7) 0.01213(17) Uani 1 d . .
H42 H 0.983149 1.136258 0.452974 0.015 Uiso 1 calc . .
C32 C 1.04840(10) 1.28274(8) 0.39342(7) 0.01537(19) Uani 1 d . .
H41 H 1.145278 1.290372 0.407432 0.018 Uiso 1 calc . .
H40 H 1.029022 1.310109 0.330744 0.018 Uiso 1 calc . .
C33 C 1.01974(11) 1.34805(8) 0.47013(7) 0.01660(19) Uani 1 d . .
H39 H 1.045459 1.324083 0.533346 0.02 Uiso 1 calc . .
H38 H 1.075148 1.424527 0.470288 0.02 Uiso 1 calc . .
C34 C 0.87018(11) 1.33463(8) 0.45183(8) 0.0176(2) Uani 1 d . .
H36 H 0.845972 1.363284 0.390664 0.021 Uiso 1 calc . .
H37 H 0.852938 1.375687 0.50293 0.021 Uiso 1 calc . .
C35 C 0.78223(11) 1.21676(9) 0.44856(8) 0.0187(2) Uani 1 d . .
H35 H 0.685473 1.209514 0.435111 0.022 Uiso 1 calc . .
H34 H 0.801939 1.189747 0.51136 0.022 Uiso 1 calc . .
C36 C 0.80822(10) 1.14949(8) 0.37223(7) 0.01509(18) Uani 1 d . .
H32 H 0.781317 1.172171 0.308654 0.018 Uiso 1 calc . .
H33 H 0.752997 1.073231 0.373585 0.018 Uiso 1 calc . .
C37 C 1.17350(11) 0.99380(8) 0.25655(7) 0.01575(19) Uani 1 d . .
H44 H 1.093898 0.932593 0.224042 0.019 Uiso 1 calc . .
H52 H 1.199095 1.047481 0.210069 0.019 Uiso 1 calc . .
C38 C 1.29174(11) 0.95575(8) 0.29270(8) 0.0182(2) Uani 1 d . .
H51 H 1.261882 0.896227 0.333243 0.022 Uiso 1 calc . .
H50 H 1.318115 0.9282 0.237794 0.022 Uiso 1 calc . .
H1B H 0.9103(14) 0.6734(11) 0.2142(10) 0.019(3) Uiso 1 d . .
H2B H 1.0413(15) 1.1571(11) 0.2386(10) 0.020(3) Uiso 1 d . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 O3 1.4461(8) . ?
S1 O1 1.4543(8) . ?
S1 O2 1.4586(8) . ?
S1 C3 1.7786(10) . ?
S2 O5 1.4498(8) . ?
S2 O6 1.4586(7) . ?
S2 O4 1.4601(8) . ?
S2 C30 1.7732(10) . ?
P1 C4 1.8059(10) . ?
P1 C12 1.8153(10) . ?
P1 C5 1.8248(10) . ?
P1 H1B 1.292(14) . ?
P2 C23 1.8105(10) . ?
P2 C24 1.8190(10) . ?
P2 C31 1.8228(10) . ?
P2 H2B 1.305(14) . ?
C1 C2 1.3871(14) . ?
C1 C15 1.3927(15) . ?
C1 H1 0.95 . ?
C2 C3 1.3921(14) . ?
C2 H19 0.95 . ?
C3 C4 1.4019(13) . ?
C4 C16 1.4040(13) . ?
C5 C6 1.5388(14) . ?
C5 C14 1.5417(14) . ?
C5 H5 1 . ?
C6 C7 1.5303(14) . ?
C6 H7 0.99 . ?
C6 H6 0.99 . ?
C7 C8 1.5300(16) . ?
C7 H13 0.99 . ?
C7 H14 0.99 . ?
C8 C13 1.5261(15) . ?
C8 H2 0.99 . ?
C8 H8 0.99 . ?
C9 C19 1.5263(17) . ?
C9 C10 1.5272(17) . ?
C9 H3 0.99 . ?
C9 H28 0.99 . ?
C10 C11 1.5278(14) . ?
C10 H27 0.99 . ?
C10 H26 0.99 . ?
C11 C12 1.5340(14) . ?
C11 H25 0.99 . ?
C11 H4 0.99 . ?
C12 C18 1.5357(14) . ?
C12 H24 1 . ?
C13 C14 1.5298(14) . ?
C13 H9 0.99 . ?
C13 H10 0.99 . ?
C14 H12 0.99 . ?
C14 H11 0.99 . ?
C15 C16 1.3977(14) . ?
C15 C17 1.5064(14) . ?
C16 H15 0.95 . ?
C17 H17 0.98 . ?
C17 H18 0.98 . ?
C17 H16 0.98 . ?
C18 C19 1.5308(15) . ?
C18 H22 0.99 . ?
C18 H23 0.99 . ?
C19 H21 0.99 . ?
C19 H20 0.99 . ?
C20 C21 1.3933(15) . ?
C20 C29 1.3939(14) . ?
C20 H29 0.95 . ?
C21 C22 1.4013(14) . ?
C21 C28 1.5065(14) . ?
C22 C23 1.4024(13) . ?
C22 H53 0.95 . ?
C23 C30 1.4072(13) . ?
C24 C37 1.5354(14) . ?
C24 C25 1.5385(13) . ?
C24 H43 1 . ?
C25 C26 1.5302(14) . ?
C25 H45 0.99 . ?
C25 H46 0.99 . ?
C26 C27 1.5273(16) . ?
C26 H48 0.99 . ?
C26 H47 0.99 . ?
C27 C38 1.5268(15) . ?
C27 H30 0.99 . ?
C27 H49 0.99 . ?
C28 H31 0.98 . ?
C28 H56 0.98 . ?
C28 H55 0.98 . ?
C29 C30 1.3867(13) . ?
C29 H54 0.95 . ?
C31 C36 1.5364(14) . ?
C31 C32 1.5477(14) . ?
C31 H42 1 . ?
C32 C33 1.5320(14) . ?
C32 H41 0.99 . ?
C32 H40 0.99 . ?
C33 C34 1.5230(15) . ?
C33 H39 0.99 . ?
C33 H38 0.99 . ?
C34 C35 1.5279(15) . ?
C34 H36 0.99 . ?
C34 H37 0.99 . ?
C35 C36 1.5297(14) . ?
C35 H35 0.99 . ?
C35 H34 0.99 . ?
C36 H32 0.99 . ?
C36 H33 0.99 . ?
C37 C38 1.5316(14) . ?
C37 H44 0.99 . ?
C37 H52 0.99 . ?
C38 H51 0.99 . ?
C38 H50 0.99 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 S1 O1 113.85(5) . . ?
O3 S1 O2 114.09(5) . . ?
O1 S1 O2 112.90(5) . . ?
O3 S1 C3 105.92(5) . . ?
O1 S1 C3 105.05(5) . . ?
O2 S1 C3 103.77(5) . . ?
O5 S2 O6 114.41(5) . . ?
O5 S2 O4 113.43(5) . . ?
O6 S2 O4 112.74(5) . . ?
O5 S2 C30 107.04(5) . . ?
O6 S2 C30 103.31(4) . . ?
O4 S2 C30 104.69(5) . . ?
C4 P1 C12 114.55(4) . . ?
C4 P1 C5 117.34(4) . . ?
C12 P1 C5 115.11(5) . . ?
C4 P1 H1B 100.7(6) . . ?
C12 P1 H1B 102.4(6) . . ?
C5 P1 H1B 103.4(6) . . ?
C23 P2 C24 115.90(5) . . ?
C23 P2 C31 116.26(5) . . ?
C24 P2 C31 113.53(5) . . ?
C23 P2 H2B 100.5(6) . . ?
C24 P2 H2B 103.0(6) . . ?
C31 P2 H2B 104.9(6) . . ?
C2 C1 C15 121.29(9) . . ?
C2 C1 H1 119.4 . . ?
C15 C1 H1 119.4 . . ?
C1 C2 C3 120.26(9) . . ?
C1 C2 H19 119.9 . . ?
C3 C2 H19 119.9 . . ?
C2 C3 C4 119.59(9) . . ?
C2 C3 S1 118.56(7) . . ?
C4 C3 S1 121.77(7) . . ?
C3 C4 C16 119.40(9) . . ?
C3 C4 P1 125.30(7) . . ?
C16 C4 P1 115.28(7) . . ?
C6 C5 C14 110.25(8) . . ?
C6 C5 P1 112.00(7) . . ?
C14 C5 P1 109.72(7) . . ?
C6 C5 H5 108.3 . . ?
C14 C5 H5 108.3 . . ?
P1 C5 H5 108.3 . . ?
C7 C6 C5 109.73(9) . . ?
C7 C6 H7 109.7 . . ?
C5 C6 H7 109.7 . . ?
C7 C6 H6 109.7 . . ?
C5 C6 H6 109.7 . . ?
H7 C6 H6 108.2 . . ?
C8 C7 C6 111.71(9) . . ?
C8 C7 H13 109.3 . . ?
C6 C7 H13 109.3 . . ?
C8 C7 H14 109.3 . . ?
C6 C7 H14 109.3 . . ?
H13 C7 H14 107.9 . . ?
C13 C8 C7 111.40(9) . . ?
C13 C8 H2 109.3 . . ?
C7 C8 H2 109.3 . . ?
C13 C8 H8 109.3 . . ?
C7 C8 H8 109.3 . . ?
H2 C8 H8 108 . . ?
C19 C9 C10 110.60(9) . . ?
C19 C9 H3 109.5 . . ?
C10 C9 H3 109.5 . . ?
C19 C9 H28 109.5 . . ?
C10 C9 H28 109.5 . . ?
H3 C9 H28 108.1 . . ?
C9 C10 C11 111.79(9) . . ?
C9 C10 H27 109.3 . . ?
C11 C10 H27 109.3 . . ?
C9 C10 H26 109.3 . . ?
C11 C10 H26 109.3 . . ?
H27 C10 H26 107.9 . . ?
C10 C11 C12 110.68(8) . . ?
C10 C11 H25 109.5 . . ?
C12 C11 H25 109.5 . . ?
C10 C11 H4 109.5 . . ?
C12 C11 H4 109.5 . . ?
H25 C11 H4 108.1 . . ?
C11 C12 C18 111.50(8) . . ?
C11 C12 P1 108.78(7) . . ?
C18 C12 P1 108.40(7) . . ?
C11 C12 H24 109.4 . . ?
C18 C12 H24 109.4 . . ?
P1 C12 H24 109.4 . . ?
C8 C13 C14 111.77(9) . . ?
C8 C13 H9 109.3 . . ?
C14 C13 H9 109.3 . . ?
C8 C13 H10 109.3 . . ?
C14 C13 H10 109.3 . . ?
H9 C13 H10 107.9 . . ?
C13 C14 C5 109.66(8) . . ?
C13 C14 H12 109.7 . . ?
C5 C14 H12 109.7 . . ?
C13 C14 H11 109.7 . . ?
C5 C14 H11 109.7 . . ?
H12 C14 H11 108.2 . . ?
C1 C15 C16 118.42(9) . . ?
C1 C15 C17 120.73(9) . . ?
C16 C15 C17 120.85(9) . . ?
C15 C16 C4 121.00(9) . . ?
C15 C16 H15 119.5 . . ?
C4 C16 H15 119.5 . . ?
C15 C17 H17 109.5 . . ?
C15 C17 H18 109.5 . . ?
H17 C17 H18 109.5 . . ?
C15 C17 H16 109.5 . . ?
H17 C17 H16 109.5 . . ?
H18 C17 H16 109.5 . . ?
C19 C18 C12 110.47(9) . . ?
C19 C18 H22 109.6 . . ?
C12 C18 H22 109.6 . . ?
C19 C18 H23 109.6 . . ?
C12 C18 H23 109.6 . . ?
H22 C18 H23 108.1 . . ?
C9 C19 C18 111.43(9) . . ?
C9 C19 H21 109.3 . . ?
C18 C19 H21 109.3 . . ?
C9 C19 H20 109.3 . . ?
C18 C19 H20 109.3 . . ?
H21 C19 H20 108 . . ?
C21 C20 C29 120.68(9) . . ?
C21 C20 H29 119.7 . . ?
C29 C20 H29 119.7 . . ?
C20 C21 C22 118.64(9) . . ?
C20 C21 C28 120.94(9) . . ?
C22 C21 C28 120.42(10) . . ?
C21 C22 C23 121.20(9) . . ?
C21 C22 H53 119.4 . . ?
C23 C22 H53 119.4 . . ?
C22 C23 C30 119.00(9) . . ?
C22 C23 P2 115.98(7) . . ?
C30 C23 P2 124.97(7) . . ?
C37 C24 C25 110.93(8) . . ?
C37 C24 P2 110.47(7) . . ?
C25 C24 P2 110.52(7) . . ?
C37 C24 H43 108.3 . . ?
C25 C24 H43 108.3 . . ?
P2 C24 H43 108.3 . . ?
C26 C25 C24 109.44(8) . . ?
C26 C25 H45 109.8 . . ?
C24 C25 H45 109.8 . . ?
C26 C25 H46 109.8 . . ?
C24 C25 H46 109.8 . . ?
H45 C25 H46 108.2 . . ?
C27 C26 C25 111.87(9) . . ?
C27 C26 H48 109.2 . . ?
C25 C26 H48 109.2 . . ?
C27 C26 H47 109.2 . . ?
C25 C26 H47 109.2 . . ?
H48 C26 H47 107.9 . . ?
C38 C27 C26 111.12(9) . . ?
C38 C27 H30 109.4 . . ?
C26 C27 H30 109.4 . . ?
C38 C27 H49 109.4 . . ?
C26 C27 H49 109.4 . . ?
H30 C27 H49 108 . . ?
C21 C28 H31 109.5 . . ?
C21 C28 H56 109.5 . . ?
H31 C28 H56 109.5 . . ?
C21 C28 H55 109.5 . . ?
H31 C28 H55 109.5 . . ?
H56 C28 H55 109.5 . . ?
C30 C29 C20 120.59(9) . . ?
C30 C29 H54 119.7 . . ?
C20 C29 H54 119.7 . . ?
C29 C30 C23 119.82(9) . . ?
C29 C30 S2 119.27(8) . . ?
C23 C30 S2 120.88(7) . . ?
C36 C31 C32 110.79(8) . . ?
C36 C31 P2 111.24(7) . . ?
C32 C31 P2 109.22(7) . . ?
C36 C31 H42 108.5 . . ?
C32 C31 H42 108.5 . . ?
P2 C31 H42 108.5 . . ?
C33 C32 C31 110.17(8) . . ?
C33 C32 H41 109.6 . . ?
C31 C32 H41 109.6 . . ?
C33 C32 H40 109.6 . . ?
C31 C32 H40 109.6 . . ?
H41 C32 H40 108.1 . . ?
C34 C33 C32 110.57(8) . . ?
C34 C33 H39 109.5 . . ?
C32 C33 H39 109.5 . . ?
C34 C33 H38 109.5 . . ?
C32 C33 H38 109.5 . . ?
H39 C33 H38 108.1 . . ?
C33 C34 C35 110.54(8) . . ?
C33 C34 H36 109.5 . . ?
C35 C34 H36 109.5 . . ?
C33 C34 H37 109.5 . . ?
C35 C34 H37 109.5 . . ?
H36 C34 H37 108.1 . . ?
C34 C35 C36 111.43(9) . . ?
C34 C35 H35 109.3 . . ?
C36 C35 H35 109.3 . . ?
C34 C35 H34 109.3 . . ?
C36 C35 H34 109.3 . . ?
H35 C35 H34 108 . . ?
C35 C36 C31 109.87(8) . . ?
C35 C36 H32 109.7 . . ?
C31 C36 H32 109.7 . . ?
C35 C36 H33 109.7 . . ?
C31 C36 H33 109.7 . . ?
H32 C36 H33 108.2 . . ?
C38 C37 C24 109.96(8) . . ?
C38 C37 H44 109.7 . . ?
C24 C37 H44 109.7 . . ?
C38 C37 H52 109.7 . . ?
C24 C37 H52 109.7 . . ?
H44 C37 H52 108.2 . . ?
C27 C38 C37 112.21(9) . . ?
C27 C38 H51 109.2 . . ?
C37 C38 H51 109.2 . . ?
C27 C38 H50 109.2 . . ?
C37 C38 H50 109.2 . . ?
H51 C38 H50 107.9 . . ?
####################################################################### 
# 
# 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_EM230518
_database_code_depnum_ccdc_archive 'CCDC 1846731'
_audit_update_record             
;
2018-06-01 deposited with the CCDC.
2018-07-05 downloaded from the CCDC.
;
_cell_length_a                   8.5873(12)
_cell_length_b                   11.2568(15)
_cell_length_c                   14.919(2)
_cell_angle_alpha                109.369(4)
_cell_angle_beta                 102.428(5)
_cell_angle_gamma                95.686(4)
_cell_volume                     1305.7(3)

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1 '
_symmetry_space_group_name_Hall  ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
P 0.1023 0.0942 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645
1.1149 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
S 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720
0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784
-9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            2

# Given Formula = C23 H24 Cl4 O5 P1 S5 
# Dc =      1.81 Fooo =    730.00 Mu =      9.53 M =    713.56
# Found Formula = C23 H25 Cl4 O5 P1 S1 
# Dc =      1.49 FOOO =    604.00 Mu =      6.27 M =    586.30

_chemical_formula_sum            'C23 H25 Cl4 O5 P1 S1'
_chemical_formula_moiety         'C23 H25 Cl4 O5 P1 S1'
_chemical_compound_source        ?
_chemical_formula_weight         586.30


_cell_measurement_reflns_used    9866
_cell_measurement_theta_min      2
_cell_measurement_theta_max      31
_cell_measurement_temperature    100

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.030
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_max          0.150

_exptl_crystal_density_diffrn    1.491
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             604
_exptl_absorpt_coefficient_mu    0.627

# Sheldrick geometric approximatio 0.94 0.98 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_T_max  0.98
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       'φ & ω scans'

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXS 86 (Sheldrick, 1986)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      100
_diffrn_reflns_number            30680
_reflns_number_total             7859
_diffrn_reflns_av_R_equivalents  0.030
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 7859 
# Theoretical number of reflections is about 17328 


_diffrn_reflns_theta_min         1.500
_diffrn_reflns_theta_max         31.461
_diffrn_measured_fraction_theta_max 0.905

_diffrn_reflns_theta_full        26.113
_diffrn_measured_fraction_theta_full 0.996


_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_reflns_limit_h_min              -12
_reflns_limit_h_max              12
_reflns_limit_k_min              -16
_reflns_limit_k_max              15
_reflns_limit_l_min              0
_reflns_limit_l_max              21


_atom_sites_solution_primary     direct #heavy,direct,difmap,geom,iterative
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.60
_refine_diff_density_max         0.90


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_refine_ls_number_reflns         6890
_refine_ls_number_restraints     0
_refine_ls_number_parameters     307
_refine_ls_wR_factor_ref         0.0335
_refine_ls_goodness_of_fit_ref   1.0330
_refine_ls_shift/su_max          0.0024420
_refine_ls_shift/su_mean         0.0000871


# The values computed with all filters except I/sigma 
_refine_ls_R_factor_all          0.0323
_refine_ls_wR_factor_all         0.0378

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                7112
_refine_ls_R_factor_gt           0.0287
_refine_ls_wR_factor_gt          0.0339

# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration .


_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 0.582 0.491 0.310 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
S1 S 0.32274(3) -0.45201(2) 0.761350(16) 0.0111 1.0000 Uani . . . . . .
Cl2 Cl 0.74450(3) -0.20923(2) 1.02350(2) 0.0230 1.0000 Uani . . . . . .
Cl3 Cl 0.80830(4) -0.46836(3) 0.93984(2) 0.0279 1.0000 Uani . . . . . .
Cl4 Cl -0.05764(4) -0.71317(3) 0.78631(2) 0.0299 1.0000 Uani . . . . . .
Cl5 Cl -0.02368(5) -0.91794(3) 0.61369(3) 0.0422 1.0000 Uani . . . . . .
P1 P 0.41564(3) -0.18481(2) 0.711283(16) 0.0094 1.0000 Uani . . . . . .
O1 O 0.54706(9) 0.03390(7) 0.88557(5) 0.0164 1.0000 Uani . . . . . .
O2 O 0.32491(9) -0.49379(7) 0.84387(6) 0.0185 1.0000 Uani . . . . . .
O3 O 0.48223(8) -0.39496(7) 0.76076(6) 0.0161 1.0000 Uani . . . . . .
O4 O 0.23257(9) -0.54890(7) 0.66674(5) 0.0165 1.0000 Uani . . . . . .
O5 O 0.64782(8) -0.25267(7) 0.59913(5) 0.0163 1.0000 Uani . . . . . .
C1 C 0.64746(14) 0.12397(11) 0.97812(8) 0.0245 1.0000 Uani . . . . . .
H13 H 0.7479 0.1568 0.9696 0.0500 1.0000 Uiso R . . . . .
H12 H 0.6684 0.0813 1.0249 0.0500 1.0000 Uiso R . . . . .
H100 H 0.5923 0.1930 1.0029 0.0500 1.0000 Uiso R . . . . .
C2 C 0.51616(11) 0.07447(9) 0.80845(7) 0.0134 1.0000 Uani . . . . . .
C3 C 0.44518(11) -0.02332(8) 0.71622(7) 0.0119 1.0000 Uani . . . . . .
C4 C 0.24779(10) -0.21386(8) 0.76076(6) 0.0103 1.0000 Uani . . . . . .
C5 C 0.14794(11) -0.12188(8) 0.77577(7) 0.0121 1.0000 Uani . . . . . .
H51 H 0.1745 -0.0470 0.7642 0.0500 1.0000 Uiso R . . . . .
C6 C 0.00933(11) -0.13935(9) 0.80818(7) 0.0140 1.0000 Uani . . . . . .
C7 C -0.09888(12) -0.04125(10) 0.82189(8) 0.0195 1.0000 Uani . . . . . .
H72 H -0.1696 -0.0523 0.7593 0.0500 1.0000 Uiso R . . . . .
H71 H -0.0333 0.0430 0.8500 0.0500 1.0000 Uiso R . . . . .
H73 H -0.1623 -0.0520 0.8653 0.0500 1.0000 Uiso R . . . . .
C8 C 0.30143(12) -0.44263(9) 0.38856(7) 0.0162 1.0000 Uani . . . . . .
H81 H 0.2787 -0.4946 0.3227 0.0500 1.0000 Uiso R . . . . .
C9 C 0.46266(11) -0.39222(9) 0.44189(7) 0.0134 1.0000 Uani . . . . . .
H91 H 0.5458 -0.4112 0.4121 0.0500 1.0000 Uiso R . . . . .
C10 C 0.49677(11) -0.31287(8) 0.54074(6) 0.0114 1.0000 Uani . . . . . .
C11 C 0.36969(11) -0.28930(8) 0.58611(6) 0.0112 1.0000 Uani . . . . . .
C12 C 0.20914(11) -0.34178(9) 0.53135(7) 0.0147 1.0000 Uani . . . . . .
H121 H 0.1256 -0.3264 0.5620 0.0500 1.0000 Uiso R . . . . .
C13 C 0.17410(12) -0.41704(10) 0.43182(7) 0.0173 1.0000 Uani . . . . . .
H131 H 0.0675 -0.4495 0.3946 0.0500 1.0000 Uiso R . . . . .
C14 C 0.54932(12) 0.20144(9) 0.81575(8) 0.0189 1.0000 Uani . . . . . .
H141 H 0.5952 0.2669 0.8765 0.0500 1.0000 Uiso R . . . . .
C15 C 0.51289(14) 0.22928(10) 0.72995(9) 0.0228 1.0000 Uani . . . . . .
H151 H 0.5345 0.3134 0.7340 0.0500 1.0000 Uiso R . . . . .
C16 C 0.44487(15) 0.13320(11) 0.63840(9) 0.0235 1.0000 Uani . . . . . .
H161 H 0.4234 0.1533 0.5820 0.0500 1.0000 Uiso R . . . . .
C17 C 0.40975(13) 0.00661(10) 0.63135(7) 0.0174 1.0000 Uani . . . . . .
H171 H 0.3632 -0.0576 0.5702 0.0500 1.0000 Uiso R . . . . .
C18 C 0.20886(11) -0.32578(8) 0.77988(6) 0.0112 1.0000 Uani . . . . . .
C19 C 0.07153(12) -0.34300(9) 0.81302(7) 0.0146 1.0000 Uani . . . . . .
H191 H 0.0455 -0.4168 0.8255 0.0500 1.0000 Uiso R . . . . .
C20 C -0.02766(11) -0.25150(9) 0.82607(7) 0.0152 1.0000 Uani . . . . . .
H201 H -0.1193 -0.2650 0.8475 0.0500 1.0000 Uiso R . . . . .
C21 C 0.78109(11) -0.27093(10) 0.55505(7) 0.0174 1.0000 Uani . . . . . .
H211 H 0.7864 -0.3606 0.5314 0.0500 1.0000 Uiso R . . . . .
H213 H 0.8805 -0.2240 0.6035 0.0500 1.0000 Uiso R . . . . .
H212 H 0.7656 -0.2411 0.5013 0.0500 1.0000 Uiso R . . . . .
C22 C 0.68072(12) -0.37502(10) 0.99854(8) 0.0176 1.0000 Uani . . . . . .
H221 H 0.5705 -0.4031 0.9570 0.0500 1.0000 Uiso R . . . . .
H222 H 0.6819 -0.3877 1.0600 0.0500 1.0000 Uiso R . . . . .
C23 C 0.07558(15) -0.78112(11) 0.71806(9) 0.0245 1.0000 Uani . . . . . .
H232 H 0.1606 -0.8042 0.7597 0.0500 1.0000 Uiso R . . . . .
H231 H 0.1259 -0.7178 0.6968 0.0500 1.0000 Uiso R . . . . .
H11 H 0.5421 -0.1981 0.7588 0.0500 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 . O2 . 1.4538(7) yes
S1 . O3 . 1.4570(7) yes
S1 . O4 . 1.4569(7) yes
S1 . C18 . 1.7841(9) yes
Cl2 . C22 . 1.7806(11) yes
Cl3 . C22 . 1.7613(11) yes
Cl4 . C23 . 1.7575(12) yes
Cl5 . C23 . 1.7610(12) yes
P1 . C3 . 1.7850(9) yes
P1 . C4 . 1.8040(9) yes
P1 . C11 . 1.7778(9) yes
P1 . H11 . 1.214 no
O1 . C1 . 1.4366(12) yes
O1 . C2 . 1.3580(11) yes
O5 . C10 . 1.3596(11) yes
O5 . C21 . 1.4372(11) yes
C1 . H13 . 0.955 no
C1 . H12 . 0.967 no
C1 . H100 . 0.960 no
C2 . C3 . 1.4064(12) yes
C2 . C14 . 1.3923(13) yes
C3 . C17 . 1.3953(13) yes
C4 . C5 . 1.4008(12) yes
C4 . C18 . 1.4058(12) yes
C5 . H51 . 0.931 no
C5 . C6 . 1.3977(13) yes
C6 . C7 . 1.5034(13) yes
C6 . C20 . 1.3952(13) yes
C7 . H72 . 0.959 no
C7 . H71 . 0.960 no
C7 . H73 . 0.960 no
C8 . H81 . 0.927 no
C8 . C9 . 1.3937(13) yes
C8 . C13 . 1.3921(14) yes
C9 . H91 . 0.926 no
C9 . C10 . 1.3954(12) yes
C10 . C11 . 1.4055(12) yes
C11 . C12 . 1.3967(12) yes
C12 . H121 . 0.931 no
C12 . C13 . 1.3913(13) yes
C13 . H131 . 0.928 no
C14 . H141 . 0.930 no
C14 . C15 . 1.3957(16) yes
C15 . H151 . 0.926 no
C15 . C16 . 1.3885(17) yes
C16 . H161 . 0.928 no
C16 . C17 . 1.3909(14) yes
C17 . H171 . 0.929 no
C18 . C19 . 1.3935(12) yes
C19 . H191 . 0.927 no
C19 . C20 . 1.3916(13) yes
C20 . H201 . 0.929 no
C21 . H211 . 0.962 no
C21 . H213 . 0.960 no
C21 . H212 . 0.957 no
C22 . H221 . 0.968 no
C22 . H222 . 0.972 no
C23 . H232 . 0.967 no
C23 . H231 . 0.972 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 . S1 . O3 . 113.69(5) yes
O2 . S1 . O4 . 113.28(5) yes
O3 . S1 . O4 . 113.29(4) yes
O2 . S1 . C18 . 105.05(4) yes
O3 . S1 . C18 . 105.58(4) yes
O4 . S1 . C18 . 104.83(4) yes
C3 . P1 . C4 . 109.83(4) yes
C3 . P1 . C11 . 108.60(4) yes
C4 . P1 . C11 . 108.87(4) yes
C3 . P1 . H11 . 106.5 no
C4 . P1 . H11 . 112.0 no
C11 . P1 . H11 . 111.0 no
C1 . O1 . C2 . 117.37(8) yes
C10 . O5 . C21 . 117.37(8) yes
O1 . C1 . H13 . 109.9 no
O1 . C1 . H12 . 109.2 no
H13 . C1 . H12 . 109.4 no
O1 . C1 . H100 . 109.6 no
H13 . C1 . H100 . 109.9 no
H12 . C1 . H100 . 108.9 no
O1 . C2 . C3 . 114.75(8) yes
O1 . C2 . C14 . 124.91(9) yes
C3 . C2 . C14 . 120.33(9) yes
P1 . C3 . C2 . 118.00(7) yes
P1 . C3 . C17 . 121.93(7) yes
C2 . C3 . C17 . 119.94(8) yes
P1 . C4 . C5 . 117.31(6) yes
P1 . C4 . C18 . 123.36(7) yes
C5 . C4 . C18 . 119.25(8) yes
C4 . C5 . H51 . 119.4 no
C4 . C5 . C6 . 121.59(8) yes
H51 . C5 . C6 . 119.0 no
C5 . C6 . C7 . 121.09(9) yes
C5 . C6 . C20 . 118.20(9) yes
C7 . C6 . C20 . 120.69(9) yes
C6 . C7 . H72 . 109.5 no
C6 . C7 . H71 . 109.3 no
H72 . C7 . H71 . 109.6 no
C6 . C7 . H73 . 109.3 no
H72 . C7 . H73 . 109.6 no
H71 . C7 . H73 . 109.5 no
H81 . C8 . C9 . 119.1 no
H81 . C8 . C13 . 119.3 no
C9 . C8 . C13 . 121.63(9) yes
C8 . C9 . H91 . 120.4 no
C8 . C9 . C10 . 119.04(9) yes
H91 . C9 . C10 . 120.6 no
C9 . C10 . O5 . 124.68(8) yes
C9 . C10 . C11 . 119.90(8) yes
O5 . C10 . C11 . 115.41(8) yes
P1 . C11 . C10 . 119.09(7) yes
P1 . C11 . C12 . 120.84(7) yes
C10 . C11 . C12 . 119.97(8) yes
C11 . C12 . H121 . 119.5 no
C11 . C12 . C13 . 120.32(9) yes
H121 . C12 . C13 . 120.2 no
C8 . C13 . C12 . 119.07(9) yes
C8 . C13 . H131 . 120.3 no
C12 . C13 . H131 . 120.6 no
C2 . C14 . H141 . 121.0 no
C2 . C14 . C15 . 118.80(10) yes
H141 . C14 . C15 . 120.2 no
C14 . C15 . H151 . 119.5 no
C14 . C15 . C16 . 121.30(10) yes
H151 . C15 . C16 . 119.2 no
C15 . C16 . H161 . 120.1 no
C15 . C16 . C17 . 119.85(10) yes
H161 . C16 . C17 . 120.1 no
C3 . C17 . C16 . 119.78(10) yes
C3 . C17 . H171 . 120.3 no
C16 . C17 . H171 . 119.9 no
S1 . C18 . C4 . 123.88(7) yes
S1 . C18 . C19 . 116.80(7) yes
C4 . C18 . C19 . 119.30(8) yes
C18 . C19 . H191 . 119.5 no
C18 . C19 . C20 . 120.66(9) yes
H191 . C19 . C20 . 119.9 no
C6 . C20 . C19 . 120.98(9) yes
C6 . C20 . H201 . 119.6 no
C19 . C20 . H201 . 119.4 no
O5 . C21 . H211 . 109.3 no
O5 . C21 . H213 . 109.3 no
H211 . C21 . H213 . 109.3 no
O5 . C21 . H212 . 109.6 no
H211 . C21 . H212 . 109.6 no
H213 . C21 . H212 . 109.7 no
Cl2 . C22 . Cl3 . 111.42(6) yes
Cl2 . C22 . H221 . 109.5 no
Cl3 . C22 . H221 . 109.4 no
Cl2 . C22 . H222 . 109.3 no
Cl3 . C22 . H222 . 109.2 no
H221 . C22 . H222 . 108.0 no
Cl5 . C23 . Cl4 . 112.41(7) yes
Cl5 . C23 . H232 . 109.1 no
Cl4 . C23 . H232 . 109.3 no
Cl5 . C23 . H231 . 108.9 no
Cl4 . C23 . H231 . 109.1 no
H232 . C23 . H231 . 107.9 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C9 . H91 . O4 2_646 177 0.93 2.45 3.3724(15) yes
C13 . H131 . O4 2_546 158 0.93 2.54 3.4140(15) yes
C22 . H221 . O2 . 171 0.97 2.29 3.2492(15) yes
C22 . H222 . O2 2_647 155 0.97 2.27 3.1699(15) yes
C23 . H231 . O4 . 171 0.97 2.25 3.2109(15) yes


####################################################################### 
# 
# 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_sbo060617
_database_code_depnum_ccdc_archive 'CCDC 1846732'
_audit_update_record             
;
2018-06-01 deposited with the CCDC.
2018-07-05 downloaded from the CCDC.
;

_audit_creation_date             2017-06-09T14:16:18-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C17 H25 O3 P S, C H Cl3'
_chemical_formula_sum            'C18 H26 Cl3 O3 P S'
_chemical_formula_weight         459.77
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
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                   10.7641(8)
_cell_length_b                   7.7851(6)
_cell_length_c                   25.9961(19)
_cell_angle_alpha                90
_cell_angle_beta                 95.025(2)
_cell_angle_gamma                90
_cell_volume                     2170.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9357
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      28.28
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             960

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.608
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_absorpt_correction_T_min  0.865
_exptl_absorpt_correction_T_max  0.994

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'Bruker Kappa APEX II'
_diffrn_measurement_method       ω-φ
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_number            32508
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.899
_diffrn_reflns_theta_max         25.025
_diffrn_reflns_theta_full        25.025
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_reflns_number_total             3837
_reflns_number_gt                3658
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_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-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0788P)²+11.9932P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3837
_refine_ls_number_parameters     242
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0823
_refine_ls_R_factor_gt           0.0798
_refine_ls_wR_factor_ref         0.1956
_refine_ls_wR_factor_gt          0.1939
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.688
_refine_diff_density_min         -0.98
_refine_diff_density_rms         0.11

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
CL1 Cl -0.08285(16) 0.6038(3) 0.42035(8) 0.0690(5) Uani 1 d . .
CL2 Cl -0.03338(16) 0.9702(3) 0.43492(6) 0.0653(5) Uani 1 d . .
CL3 Cl -0.00376(19) 0.8102(3) 0.33766(7) 0.0753(6) Uani 1 d . .
S1 S 0.44515(10) 0.32203(13) 0.12248(4) 0.0230(3) Uani 1 d . .
P1 P 0.45580(10) 0.74228(15) 0.15156(4) 0.0214(3) Uani 1 d . .
O1 O 0.3620(4) 0.3432(5) 0.16285(14) 0.0438(9) Uani 1 d . .
O2 O 0.5752(3) 0.3495(4) 0.13789(13) 0.0328(8) Uani 1 d . .
O3 O 0.4214(4) 0.1610(4) 0.09552(16) 0.0463(10) Uani 1 d . .
C1 C 0.2848(5) 0.8687(7) -0.03804(18) 0.0357(11) Uani 1 d . .
H22 H 0.279764 0.817943 -0.072661 0.054 Uiso 1 calc . .
H23 H 0.345625 0.962589 -0.035989 0.054 Uiso 1 calc . .
H1 H 0.202782 0.913359 -0.031125 0.054 Uiso 1 calc . .
C2 C 0.3250(4) 0.7336(6) 0.00138(16) 0.0219(9) Uani 1 d . .
C3 C 0.3686(4) 0.7807(5) 0.05148(16) 0.0206(8) Uani 1 d . .
H21 H 0.373145 0.899068 0.060342 0.025 Uiso 1 calc . .
C4 C 0.4055(4) 0.6589(5) 0.08876(15) 0.0167(8) Uani 1 d . .
C5 C 0.3301(4) 0.8519(7) 0.17614(19) 0.0317(11) Uani 1 d . .
H4 H 0.307409 0.949538 0.152125 0.038 Uiso 1 calc . .
C6 C 0.3553(4) 0.9285(6) 0.23070(16) 0.0268(10) Uani 1 d . .
H9 H 0.414972 0.856087 0.252184 0.032 Uiso 1 calc . .
H8 H 0.390048 1.045867 0.228978 0.032 Uiso 1 calc . .
C7A C 0.2295(5) 0.9324(12) 0.2530(2) 0.065(2) Uani 1 d . .
H7A1 H 0.203873 1.052545 0.258582 0.078 Uiso 1 calc . .
H7A2 H 0.234663 0.871608 0.286559 0.078 Uiso 1 calc . .
C8 C 0.3203(4) 0.5601(6) -0.01065(15) 0.0232(9) Uani 1 d . .
H3 H 0.291163 0.525289 -0.044602 0.028 Uiso 1 calc . .
C9 C 0.3573(4) 0.4366(5) 0.02587(16) 0.0213(9) Uani 1 d . .
H24 H 0.353524 0.318511 0.016663 0.026 Uiso 1 calc . .
C10 C 0.4002(3) 0.4841(5) 0.07601(14) 0.0159(8) Uani 1 d . .
C11 C 0.2122(4) 0.7411(7) 0.1786(2) 0.0354(11) Uani 1 d . .
H6 H 0.16706 0.727864 0.143966 0.043 Uiso 1 calc . .
H5 H 0.233239 0.625893 0.192978 0.043 Uiso 1 calc . .
C12 C 0.1353(4) 0.8440(7) 0.21458(18) 0.0322(11) Uani 1 d . .
H10 H 0.082839 0.930014 0.194814 0.039 Uiso 1 calc . .
H11 H 0.080464 0.766933 0.232749 0.039 Uiso 1 calc . .
C13 C 0.5976(4) 0.8591(6) 0.14901(19) 0.0304(10) Uani 1 d . .
H20 H 0.580214 0.96189 0.12645 0.037 Uiso 1 calc . .
C14 C 0.7003(4) 0.7527(6) 0.12652(17) 0.0257(9) Uani 1 d . .
H13 H 0.694333 0.630234 0.136309 0.031 Uiso 1 calc . .
H12 H 0.694196 0.76152 0.088393 0.031 Uiso 1 calc . .
C15 C 0.8221(4) 0.8320(7) 0.15037(18) 0.0305(10) Uani 1 d . .
H18 H 0.877838 0.741404 0.166016 0.037 Uiso 1 calc . .
H19 H 0.865586 0.891887 0.123553 0.037 Uiso 1 calc . .
C16A C 0.7891(6) 0.9558(12) 0.1906(3) 0.078(3) Uani 1 d . .
H16A H 0.79738 1.074989 0.178058 0.093 Uiso 1 calc . .
H16B H 0.845975 0.941087 0.222316 0.093 Uiso 1 calc . .
C17 C 0.6552(4) 0.9217(7) 0.20213(18) 0.0316(11) Uani 1 d . .
H14 H 0.614106 1.027564 0.213164 0.038 Uiso 1 calc . .
H15 H 0.650758 0.832138 0.228942 0.038 Uiso 1 calc . .
C18 C -0.0894(5) 0.8107(9) 0.3919(2) 0.0486(15) Uani 1 d . .
H25 H -0.178339 0.837203 0.380257 0.058 Uiso 1 calc . .
H1B H 0.478(5) 0.604(7) 0.183(2) 0.042(15) Uiso 1 d . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
CL1 C18 1.772(7) . ?
CL2 C18 1.743(6) . ?
CL3 C18 1.750(6) . ?
S1 O2 1.438(3) . ?
S1 O1 1.447(4) . ?
S1 O3 1.448(4) . ?
S1 C10 1.784(4) . ?
P1 C5 1.766(5) . ?
P1 C13 1.784(5) . ?
P1 C4 1.796(4) . ?
P1 H1B 1.35(6) . ?
C1 C2 1.505(6) . ?
C1 H22 0.98 . ?
C1 H23 0.98 . ?
C1 H1 0.98 . ?
C2 C8 1.386(6) . ?
C2 C3 1.394(6) . ?
C3 C4 1.389(6) . ?
C3 H21 0.95 . ?
C4 C10 1.400(6) . ?
C5 C6 1.540(6) . ?
C5 C11 1.541(7) . ?
C5 H4 1 . ?
C6 C7A 1.518(7) . ?
C6 H9 0.99 . ?
C6 H8 0.99 . ?
C7A C12 1.524(7) . ?
C7A H7A1 0.99 . ?
C7A H7A2 0.99 . ?
C8 C9 1.385(6) . ?
C8 H3 0.95 . ?
C9 C10 1.394(6) . ?
C9 H24 0.95 . ?
C11 C12 1.530(7) . ?
C11 H6 0.99 . ?
C11 H5 0.99 . ?
C12 H10 0.99 . ?
C12 H11 0.99 . ?
C13 C14 1.537(6) . ?
C13 C17 1.542(6) . ?
C13 H20 1 . ?
C14 C15 1.530(6) . ?
C14 H13 0.99 . ?
C14 H12 0.99 . ?
C15 C16A 1.487(8) . ?
C15 H18 0.99 . ?
C15 H19 0.99 . ?
C16A C17 1.521(7) . ?
C16A H16A 0.99 . ?
C16A H16B 0.99 . ?
C17 H14 0.99 . ?
C17 H15 0.99 . ?
C18 H25 1 . ?

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 115.5(2) . . ?
O2 S1 O3 112.9(2) . . ?
O1 S1 O3 110.8(3) . . ?
O2 S1 C10 106.46(18) . . ?
O1 S1 C10 105.19(19) . . ?
O3 S1 C10 105.0(2) . . ?
C5 P1 C13 116.9(2) . . ?
C5 P1 C4 108.9(2) . . ?
C13 P1 C4 110.0(2) . . ?
C5 P1 H1B 105(2) . . ?
C13 P1 H1B 109(2) . . ?
C4 P1 H1B 106(2) . . ?
C2 C1 H22 109.5 . . ?
C2 C1 H23 109.5 . . ?
H22 C1 H23 109.5 . . ?
C2 C1 H1 109.5 . . ?
H22 C1 H1 109.5 . . ?
H23 C1 H1 109.5 . . ?
C8 C2 C3 118.0(4) . . ?
C8 C2 C1 121.6(4) . . ?
C3 C2 C1 120.4(4) . . ?
C4 C3 C2 121.6(4) . . ?
C4 C3 H21 119.2 . . ?
C2 C3 H21 119.2 . . ?
C3 C4 C10 119.7(4) . . ?
C3 C4 P1 115.6(3) . . ?
C10 C4 P1 124.7(3) . . ?
C6 C5 C11 104.9(4) . . ?
C6 C5 P1 116.2(3) . . ?
C11 C5 P1 113.8(3) . . ?
C6 C5 H4 107.1 . . ?
C11 C5 H4 107.1 . . ?
P1 C5 H4 107.1 . . ?
C7A C6 C5 105.6(4) . . ?
C7A C6 H9 110.6 . . ?
C5 C6 H9 110.6 . . ?
C7A C6 H8 110.6 . . ?
C5 C6 H8 110.6 . . ?
H9 C6 H8 108.8 . . ?
C6 C7A C12 107.8(4) . . ?
C6 C7A H7A1 110.1 . . ?
C12 C7A H7A1 110.1 . . ?
C6 C7A H7A2 110.1 . . ?
C12 C7A H7A2 110.1 . . ?
H7A1 C7A H7A2 108.5 . . ?
C9 C8 C2 121.3(4) . . ?
C9 C8 H3 119.4 . . ?
C2 C8 H3 119.4 . . ?
C8 C9 C10 120.6(4) . . ?
C8 C9 H24 119.7 . . ?
C10 C9 H24 119.7 . . ?
C9 C10 C4 118.9(4) . . ?
C9 C10 S1 119.6(3) . . ?
C4 C10 S1 121.6(3) . . ?
C12 C11 C5 102.9(4) . . ?
C12 C11 H6 111.2 . . ?
C5 C11 H6 111.2 . . ?
C12 C11 H5 111.2 . . ?
C5 C11 H5 111.2 . . ?
H6 C11 H5 109.1 . . ?
C7A C12 C11 105.8(4) . . ?
C7A C12 H10 110.6 . . ?
C11 C12 H10 110.6 . . ?
C7A C12 H11 110.6 . . ?
C11 C12 H11 110.6 . . ?
H10 C12 H11 108.7 . . ?
C14 C13 C17 105.4(4) . . ?
C14 C13 P1 112.7(3) . . ?
C17 C13 P1 114.0(3) . . ?
C14 C13 H20 108.2 . . ?
C17 C13 H20 108.2 . . ?
P1 C13 H20 108.2 . . ?
C15 C14 C13 104.3(4) . . ?
C15 C14 H13 110.9 . . ?
C13 C14 H13 110.9 . . ?
C15 C14 H12 110.9 . . ?
C13 C14 H12 110.9 . . ?
H13 C14 H12 108.9 . . ?
C16A C15 C14 107.3(4) . . ?
C16A C15 H18 110.3 . . ?
C14 C15 H18 110.3 . . ?
C16A C15 H19 110.3 . . ?
C14 C15 H19 110.3 . . ?
H18 C15 H19 108.5 . . ?
C15 C16A C17 108.3(5) . . ?
C15 C16A H16A 110 . . ?
C17 C16A H16A 110 . . ?
C15 C16A H16B 110 . . ?
C17 C16A H16B 110 . . ?
H16A C16A H16B 108.4 . . ?
C16A C17 C13 101.1(4) . . ?
C16A C17 H14 111.6 . . ?
C13 C17 H14 111.6 . . ?
C16A C17 H15 111.6 . . ?
C13 C17 H15 111.6 . . ?
H14 C17 H15 109.4 . . ?
CL2 C18 CL3 110.0(3) . . ?
CL2 C18 CL1 112.4(3) . . ?
CL3 C18 CL1 109.2(3) . . ?
CL2 C18 H25 108.4 . . ?
CL3 C18 H25 108.4 . . ?
CL1 C18 H25 108.4 . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
