# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_cyz170801
_database_code_depnum_ccdc_archive 'CCDC 1573906'
_audit_update_record             
;
2017-09-12 deposited with the CCDC.
2018-11-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'(E)-(1-(2-cyclopropyl-3-tosylprop-1-en-1-yl)-2-(4-methoxyphenyl)-2-methylcyclopropyl)diphenylphosphine oxide'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H37 O4 P S'
_chemical_formula_sum            'C36 H37 O4 P S'
_chemical_formula_weight         596.68

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   8.7333(10)
_cell_length_b                   32.515(5)
_cell_length_c                   11.3552(17)
_cell_angle_alpha                90
_cell_angle_beta                 92.555(4)
_cell_angle_gamma                90
_cell_volume                     3221.2(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7823
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      22.47

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_F_000             1264
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.187
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6984
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32918
_diffrn_reflns_av_unetI/netI     0.0644
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.334
_diffrn_reflns_theta_max         27.594
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             7225
_reflns_number_gt                3918
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0643P)²+0.5266P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7225
_refine_ls_number_parameters     409
_refine_ls_number_restraints     90
_refine_ls_R_factor_all          0.1292
_refine_ls_R_factor_gt           0.0566
_refine_ls_wR_factor_ref         0.1417
_refine_ls_wR_factor_gt          0.1176
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.011
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5025(3) 0.29118(7) 0.4052(2) 0.0563(6) Uani 1 1 d . . . . .
C2 C 0.5121(2) 0.32665(7) 0.31341(18) 0.0495(6) Uani 1 1 d . . . . .
C3 C 0.4644(3) 0.28309(7) 0.2785(2) 0.0662(7) Uani 1 1 d . . . . .
H3A H 0.3576 0.2785 0.2552 0.079 Uiso 1 1 calc R U . . .
H3B H 0.5364 0.2668 0.2355 0.079 Uiso 1 1 calc R U . . .
C4 C 0.3870(2) 0.35818(6) 0.31511(19) 0.0449(5) Uani 1 1 d . . . . .
H4 H 0.3715 0.3709 0.3869 0.054 Uiso 1 1 calc R U . . .
C5 C 0.2964(2) 0.36965(7) 0.2244(2) 0.0485(5) Uani 1 1 d . . . . .
C6 C 0.1704(3) 0.40057(7) 0.2442(2) 0.0570(6) Uani 1 1 d . . . . .
H6A H 0.1224 0.3937 0.3171 0.068 Uiso 1 1 calc R U . . .
H6B H 0.0930 0.3980 0.1807 0.068 Uiso 1 1 calc R U . . .
C7 C 0.6471(3) 0.27123(9) 0.4604(3) 0.0854(9) Uani 1 1 d . . . . .
H7A H 0.6222 0.2446 0.4907 0.128 Uiso 1 1 calc R U . . .
H7B H 0.6879 0.2882 0.5234 0.128 Uiso 1 1 calc R U . . .
H7C H 0.7221 0.2683 0.4016 0.128 Uiso 1 1 calc R U . . .
C8 C 0.3801(3) 0.29487(7) 0.4931(2) 0.0513(6) Uani 1 1 d . . . . .
C9 C 0.2442(3) 0.27371(7) 0.4850(2) 0.0618(7) Uani 1 1 d . . . . .
H9 H 0.2220 0.2577 0.4185 0.074 Uiso 1 1 calc R U . . .
C10 C 0.1386(3) 0.27540(8) 0.5729(2) 0.0643(7) Uani 1 1 d . . . . .
H10 H 0.0472 0.2608 0.5650 0.077 Uiso 1 1 calc R U . . .
C11 C 0.1702(3) 0.29880(7) 0.6712(2) 0.0569(6) Uani 1 1 d . . . . .
C12 C 0.3061(3) 0.32047(8) 0.6805(2) 0.0646(7) Uani 1 1 d . . . . .
H12 H 0.3284 0.3364 0.7472 0.077 Uiso 1 1 calc R U . . .
C13 C 0.4079(3) 0.31881(7) 0.5933(2) 0.0600(6) Uani 1 1 d . . . . .
H13 H 0.4980 0.3340 0.6009 0.072 Uiso 1 1 calc R U . . .
C14 C -0.0651(4) 0.28227(12) 0.7606(3) 0.1118(12) Uani 1 1 d . . . . .
H14A H -0.1269 0.2918 0.6941 0.168 Uiso 1 1 calc R U . . .
H14B H -0.1167 0.2878 0.8318 0.168 Uiso 1 1 calc R U . . .
H14C H -0.0484 0.2532 0.7534 0.168 Uiso 1 1 calc R U . . .
C15 C 0.7641(2) 0.37367(7) 0.4077(2) 0.0536(6) Uani 1 1 d . . . . .
C16 C 0.6783(3) 0.40459(8) 0.4593(2) 0.0647(7) Uani 1 1 d . . . . .
H16 H 0.5846 0.4124 0.4241 0.078 Uiso 1 1 calc R U . . .
C17 C 0.7309(3) 0.42384(9) 0.5621(2) 0.0745(8) Uani 1 1 d . . . . .
H17 H 0.6721 0.4442 0.5957 0.089 Uiso 1 1 calc R U . . .
C18 C 0.8686(4) 0.41299(10) 0.6144(3) 0.0816(8) Uani 1 1 d . . . . .
H18 H 0.9032 0.4259 0.6836 0.098 Uiso 1 1 calc R U . . .
C19 C 0.9559(3) 0.38322(10) 0.5653(3) 0.0843(9) Uani 1 1 d . . . . .
H19 H 1.0501 0.3761 0.6010 0.101 Uiso 1 1 calc R U . . .
C20 C 0.9051(3) 0.36348(8) 0.4625(3) 0.0679(7) Uani 1 1 d . . . . .
H20 H 0.9656 0.3433 0.4299 0.082 Uiso 1 1 calc R U . . .
C21 C 0.6918(3) 0.37789(8) 0.1528(2) 0.0562(6) Uani 1 1 d . . . . .
C22 C 0.6435(3) 0.41833(8) 0.1526(2) 0.0663(7) Uani 1 1 d . . . . .
H22 H 0.6100 0.4300 0.2216 0.080 Uiso 1 1 calc R U . . .
C23 C 0.6446(3) 0.44176(9) 0.0498(3) 0.0795(8) Uani 1 1 d . . . . .
H23 H 0.6121 0.4690 0.0503 0.095 Uiso 1 1 calc R U . . .
C24 C 0.6937(3) 0.42455(13) -0.0517(3) 0.0912(10) Uani 1 1 d . . . . .
H24 H 0.6938 0.4401 -0.1205 0.109 Uiso 1 1 calc R U . . .
C25 C 0.7423(4) 0.38489(13) -0.0526(3) 0.1056(11) Uani 1 1 d . . . . .
H25 H 0.7763 0.3735 -0.1218 0.127 Uiso 1 1 calc R U . . .
C26 C 0.7417(3) 0.36145(10) 0.0485(3) 0.0847(9) Uani 1 1 d . . . . .
H26 H 0.7750 0.3343 0.0467 0.102 Uiso 1 1 calc R U . . .
C27A C 0.315(3) 0.3537(8) 0.106(2) 0.071(2) Uani 0.603(8) 1 d . U P A 1
H27A H 0.3951 0.3326 0.1057 0.085 Uiso 0.603(8) 1 calc R U P A 1
C28A C 0.3100(9) 0.37720(17) -0.0061(4) 0.0803(16) Uani 0.603(8) 1 d . U P A 1
H28A H 0.3880 0.3714 -0.0619 0.096 Uiso 0.603(8) 1 calc R U P A 1
H28B H 0.2781 0.4057 -0.0034 0.096 Uiso 0.603(8) 1 calc R U P A 1
C29A C 0.1920(8) 0.3452(3) 0.0116(6) 0.0814(16) Uani 0.603(8) 1 d . U P A 1
H29A H 0.1987 0.3199 -0.0328 0.098 Uiso 0.603(8) 1 calc R U P A 1
H29B H 0.0886 0.3543 0.0258 0.098 Uiso 0.603(8) 1 calc R U P A 1
C27B C 0.297(4) 0.3508(13) 0.102(4) 0.075(2) Uani 0.397(8) 1 d . U P A 2
H27B H 0.3890 0.3359 0.0797 0.090 Uiso 0.397(8) 1 calc R U P A 2
C28B C 0.2008(15) 0.3727(3) 0.0044(7) 0.078(2) Uani 0.397(8) 1 d . U P A 2
H28C H 0.2435 0.3715 -0.0618 0.093 Uiso 0.397(8) 1 d R U P A 2
H28D H 0.1549 0.3952 0.0200 0.093 Uiso 0.397(8) 1 d R U P A 2
C29B C 0.1475(13) 0.3353(3) 0.0589(9) 0.079(2) Uani 0.397(8) 1 d . U P A 2
H29C H 0.1462 0.3104 0.0117 0.095 Uiso 0.397(8) 1 calc R U P A 2
H29D H 0.0630 0.3376 0.1111 0.095 Uiso 0.397(8) 1 calc R U P A 2
C30 C 0.0596(2) 0.48015(7) 0.25854(19) 0.0478(5) Uani 1 1 d . . . . .
C31 C -0.0263(3) 0.47833(7) 0.3580(2) 0.0603(6) Uani 1 1 d . . . . .
H31 H 0.0064 0.4623 0.4221 0.072 Uiso 1 1 calc R U . . .
C32 C -0.1603(3) 0.50045(8) 0.3613(2) 0.0678(7) Uani 1 1 d . . . . .
H32 H -0.2171 0.4995 0.4286 0.081 Uiso 1 1 calc R U . . .
C33 C -0.2121(3) 0.52401(8) 0.2670(3) 0.0656(7) Uani 1 1 d . . . . .
C34 C -0.1260(3) 0.52496(9) 0.1692(2) 0.0719(7) Uani 1 1 d . . . . .
H34 H -0.1601 0.5406 0.1046 0.086 Uiso 1 1 calc R U . . .
C35 C 0.0095(3) 0.50353(8) 0.1636(2) 0.0611(6) Uani 1 1 d . . . . .
H35 H 0.0664 0.5049 0.0964 0.073 Uiso 1 1 calc R U . . .
C36 C -0.3603(3) 0.54750(12) 0.2734(3) 0.1136(12) Uani 1 1 d . . . . .
H36A H -0.3791 0.5626 0.2016 0.170 Uiso 1 1 d R U . . .
H36B H -0.3532 0.5663 0.3387 0.170 Uiso 1 1 d R U . . .
H36C H -0.4429 0.5286 0.2840 0.170 Uiso 1 1 d R U . . .
O1 O 0.0762(2) 0.30273(6) 0.76415(16) 0.0797(5) Uani 1 1 d . . . . .
O2 O 0.8096(2) 0.31033(5) 0.25623(16) 0.0792(6) Uani 1 1 d . . . . .
O3 O 0.3204(2) 0.45813(6) 0.35998(18) 0.0883(6) Uani 1 1 d . . . . .
O4 O 0.3018(2) 0.46378(5) 0.14440(18) 0.0861(6) Uani 1 1 d . . . . .
P1 P 0.70237(7) 0.34420(2) 0.27928(6) 0.0563(2) Uani 1 1 d . . . . .
S1 S 0.23234(7) 0.45266(2) 0.25196(6) 0.0564(2) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C3 1.486(3) . ?
C1 C8 1.500(3) . ?
C1 C7 1.529(3) . ?
C1 C2 1.559(3) . ?
C2 C4 1.499(3) . ?
C2 C3 1.524(3) . ?
C2 P1 1.815(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.324(3) . ?
C4 H4 0.9300 . ?
C5 C27A 1.46(3) . ?
C5 C6 1.514(3) . ?
C5 C27B 1.52(4) . ?
C6 S1 1.779(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.371(3) . ?
C8 C13 1.391(3) . ?
C9 C10 1.390(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.369(3) . ?
C10 H10 0.9300 . ?
C11 O1 1.371(3) . ?
C11 C12 1.380(3) . ?
C12 C13 1.361(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 O1 1.401(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C20 1.395(3) . ?
C15 C16 1.398(3) . ?
C15 P1 1.807(2) . ?
C16 C17 1.385(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.364(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.366(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.387(4) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C22 1.381(3) . ?
C21 C26 1.387(3) . ?
C21 P1 1.805(2) . ?
C22 C23 1.394(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.367(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.358(5) . ?
C24 H24 0.9300 . ?
C25 C26 1.378(4) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27A C28A 1.48(3) . ?
C27A C29A 1.51(2) . ?
C27A H27A 0.9800 . ?
C28A C29A 1.483(8) . ?
C28A H28A 0.9700 . ?
C28A H28B 0.9700 . ?
C29A H29A 0.9700 . ?
C29A H29B 0.9700 . ?
C27B C29B 1.46(3) . ?
C27B C28B 1.53(4) . ?
C27B H27B 0.9800 . ?
C28B C29B 1.451(14) . ?
C28B H28C 0.8557 . ?
C28B H28D 0.8553 . ?
C29B H29C 0.9700 . ?
C29B H29D 0.9700 . ?
C30 C35 1.374(3) . ?
C30 C31 1.384(3) . ?
C30 S1 1.758(2) . ?
C31 C32 1.376(3) . ?
C31 H31 0.9300 . ?
C32 C33 1.376(3) . ?
C32 H32 0.9300 . ?
C33 C34 1.369(4) . ?
C33 C36 1.507(4) . ?
C34 C35 1.377(3) . ?
C34 H34 0.9300 . ?
C35 H35 0.9300 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
O2 P1 1.4766(17) . ?
O3 S1 1.4293(18) . ?
O4 S1 1.4338(18) . ?

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
C3 C1 C8 121.5(2) . . ?
C3 C1 C7 117.8(2) . . ?
C8 C1 C7 111.2(2) . . ?
C3 C1 C2 59.99(15) . . ?
C8 C1 C2 116.54(18) . . ?
C7 C1 C2 121.3(2) . . ?
C4 C2 C3 116.6(2) . . ?
C4 C2 C1 115.88(18) . . ?
C3 C2 C1 57.61(15) . . ?
C4 C2 P1 117.55(15) . . ?
C3 C2 P1 118.60(16) . . ?
C1 C2 P1 116.87(16) . . ?
C1 C3 C2 62.40(15) . . ?
C1 C3 H3A 117.5 . . ?
C2 C3 H3A 117.5 . . ?
C1 C3 H3B 117.5 . . ?
C2 C3 H3B 117.5 . . ?
H3A C3 H3B 114.6 . . ?
C5 C4 C2 126.4(2) . . ?
C5 C4 H4 116.8 . . ?
C2 C4 H4 116.8 . . ?
C4 C5 C27A 122.0(11) . . ?
C4 C5 C6 119.0(2) . . ?
C27A C5 C6 119.0(11) . . ?
C4 C5 C27B 124.8(16) . . ?
C6 C5 C27B 115.9(16) . . ?
C5 C6 S1 114.70(15) . . ?
C5 C6 H6A 108.6 . . ?
S1 C6 H6A 108.6 . . ?
C5 C6 H6B 108.6 . . ?
S1 C6 H6B 108.6 . . ?
H6A C6 H6B 107.6 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C13 117.1(2) . . ?
C9 C8 C1 123.8(2) . . ?
C13 C8 C1 119.0(2) . . ?
C8 C9 C10 122.1(2) . . ?
C8 C9 H9 118.9 . . ?
C10 C9 H9 118.9 . . ?
C11 C10 C9 119.4(2) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C10 C11 O1 125.0(2) . . ?
C10 C11 C12 119.2(2) . . ?
O1 C11 C12 115.8(2) . . ?
C13 C12 C11 120.8(2) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C8 121.4(2) . . ?
C12 C13 H13 119.3 . . ?
C8 C13 H13 119.3 . . ?
O1 C14 H14A 109.5 . . ?
O1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C20 C15 C16 117.6(2) . . ?
C20 C15 P1 117.4(2) . . ?
C16 C15 P1 124.99(18) . . ?
C17 C16 C15 121.0(2) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C18 C17 C16 120.2(3) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C17 C18 C19 120.2(3) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C18 C19 C20 120.5(3) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C19 C20 C15 120.5(3) . . ?
C19 C20 H20 119.7 . . ?
C15 C20 H20 119.7 . . ?
C22 C21 C26 118.2(2) . . ?
C22 C21 P1 125.71(19) . . ?
C26 C21 P1 116.0(2) . . ?
C21 C22 C23 120.5(3) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C24 C23 C22 119.8(3) . . ?
C24 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C25 C24 C23 120.3(3) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C24 C25 C26 120.4(3) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C25 C26 C21 120.7(3) . . ?
C25 C26 H26 119.6 . . ?
C21 C26 H26 119.6 . . ?
C5 C27A C28A 127.5(19) . . ?
C5 C27A C29A 127.8(18) . . ?
C28A C27A C29A 59.5(10) . . ?
C5 C27A H27A 110.9 . . ?
C28A C27A H27A 110.9 . . ?
C29A C27A H27A 110.9 . . ?
C27A C28A C29A 61.2(8) . . ?
C27A C28A H28A 117.7 . . ?
C29A C28A H28A 117.7 . . ?
C27A C28A H28B 117.6 . . ?
C29A C28A H28B 117.7 . . ?
H28A C28A H28B 114.8 . . ?
C28A C29A C27A 59.3(10) . . ?
C28A C29A H29A 117.8 . . ?
C27A C29A H29A 117.8 . . ?
C28A C29A H29B 117.8 . . ?
C27A C29A H29B 117.8 . . ?
H29A C29A H29B 115.0 . . ?
C29B C27B C5 114(3) . . ?
C29B C27B C28B 57.8(14) . . ?
C5 C27B C28B 117(3) . . ?
C29B C27B H27B 118.2 . . ?
C5 C27B H27B 118.2 . . ?
C28B C27B H27B 118.2 . . ?
C29B C28B C27B 58.7(14) . . ?
C29B C28B H28C 119.8 . . ?
C27B C28B H28C 111.5 . . ?
C29B C28B H28D 117.8 . . ?
C27B C28B H28D 119.6 . . ?
H28C C28B H28D 116.6 . . ?
C28B C29B C27B 63.5(17) . . ?
C28B C29B H29C 117.4 . . ?
C27B C29B H29C 117.4 . . ?
C28B C29B H29D 117.4 . . ?
C27B C29B H29D 117.4 . . ?
H29C C29B H29D 114.5 . . ?
C35 C30 C31 119.9(2) . . ?
C35 C30 S1 119.47(17) . . ?
C31 C30 S1 120.68(18) . . ?
C32 C31 C30 119.5(2) . . ?
C32 C31 H31 120.2 . . ?
C30 C31 H31 120.2 . . ?
C31 C32 C33 121.3(2) . . ?
C31 C32 H32 119.3 . . ?
C33 C32 H32 119.3 . . ?
C34 C33 C32 118.1(2) . . ?
C34 C33 C36 122.1(3) . . ?
C32 C33 C36 119.8(3) . . ?
C33 C34 C35 122.0(2) . . ?
C33 C34 H34 119.0 . . ?
C35 C34 H34 119.0 . . ?
C30 C35 C34 119.2(2) . . ?
C30 C35 H35 120.4 . . ?
C34 C35 H35 120.4 . . ?
C33 C36 H36A 109.5 . . ?
C33 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C33 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C11 O1 C14 119.3(2) . . ?
O2 P1 C21 108.76(10) . . ?
O2 P1 C15 111.70(11) . . ?
C21 P1 C15 108.86(11) . . ?
O2 P1 C2 113.42(11) . . ?
C21 P1 C2 110.24(10) . . ?
C15 P1 C2 103.73(10) . . ?
O3 S1 O4 117.91(13) . . ?
O3 S1 C30 109.27(10) . . ?
O4 S1 C30 107.71(11) . . ?
O3 S1 C6 108.15(12) . . ?
O4 S1 C6 109.71(12) . . ?
C30 S1 C6 103.09(10) . . ?

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
C3 C1 C2 C4 106.4(2) . . . . ?
C8 C1 C2 C4 -6.4(3) . . . . ?
C7 C1 C2 C4 -147.4(2) . . . . ?
C8 C1 C2 C3 -112.8(2) . . . . ?
C7 C1 C2 C3 106.2(3) . . . . ?
C3 C1 C2 P1 -108.30(19) . . . . ?
C8 C1 C2 P1 138.94(18) . . . . ?
C7 C1 C2 P1 -2.1(3) . . . . ?
C8 C1 C3 C2 104.5(2) . . . . ?
C7 C1 C3 C2 -112.0(2) . . . . ?
C4 C2 C3 C1 -105.1(2) . . . . ?
P1 C2 C3 C1 105.29(19) . . . . ?
C3 C2 C4 C5 -60.6(3) . . . . ?
C1 C2 C4 C5 -125.6(2) . . . . ?
P1 C2 C4 C5 89.4(2) . . . . ?
C2 C4 C5 C27A -3.7(12) . . . . ?
C2 C4 C5 C6 176.92(19) . . . . ?
C2 C4 C5 C27B 3.8(19) . . . . ?
C4 C5 C6 S1 79.7(2) . . . . ?
C27A C5 C6 S1 -99.7(11) . . . . ?
C27B C5 C6 S1 -106.5(17) . . . . ?
C3 C1 C8 C9 32.0(3) . . . . ?
C7 C1 C8 C9 -113.6(3) . . . . ?
C2 C1 C8 C9 101.6(3) . . . . ?
C3 C1 C8 C13 -152.5(2) . . . . ?
C7 C1 C8 C13 61.9(3) . . . . ?
C2 C1 C8 C13 -82.9(3) . . . . ?
C13 C8 C9 C10 -0.8(3) . . . . ?
C1 C8 C9 C10 174.8(2) . . . . ?
C8 C9 C10 C11 -0.1(4) . . . . ?
C9 C10 C11 O1 -179.5(2) . . . . ?
C9 C10 C11 C12 0.4(4) . . . . ?
C10 C11 C12 C13 0.1(4) . . . . ?
O1 C11 C12 C13 -179.9(2) . . . . ?
C11 C12 C13 C8 -1.0(4) . . . . ?
C9 C8 C13 C12 1.3(4) . . . . ?
C1 C8 C13 C12 -174.5(2) . . . . ?
C20 C15 C16 C17 -1.0(4) . . . . ?
P1 C15 C16 C17 175.95(19) . . . . ?
C15 C16 C17 C18 0.5(4) . . . . ?
C16 C17 C18 C19 0.3(4) . . . . ?
C17 C18 C19 C20 -0.5(4) . . . . ?
C18 C19 C20 C15 -0.1(4) . . . . ?
C16 C15 C20 C19 0.8(3) . . . . ?
P1 C15 C20 C19 -176.4(2) . . . . ?
C26 C21 C22 C23 0.2(4) . . . . ?
P1 C21 C22 C23 178.1(2) . . . . ?
C21 C22 C23 C24 0.1(4) . . . . ?
C22 C23 C24 C25 -0.5(5) . . . . ?
C23 C24 C25 C26 0.5(5) . . . . ?
C24 C25 C26 C21 -0.2(5) . . . . ?
C22 C21 C26 C25 -0.2(4) . . . . ?
P1 C21 C26 C25 -178.3(3) . . . . ?
C4 C5 C27A C28A -136.0(15) . . . . ?
C6 C5 C27A C28A 43(2) . . . . ?
C4 C5 C27A C29A 146.3(17) . . . . ?
C6 C5 C27A C29A -34(3) . . . . ?
C5 C27A C28A C29A -116(2) . . . . ?
C5 C27A C29A C28A 116(3) . . . . ?
C4 C5 C27B C29B 124(2) . . . . ?
C6 C5 C27B C29B -49(3) . . . . ?
C4 C5 C27B C28B -171.0(15) . . . . ?
C6 C5 C27B C28B 16(3) . . . . ?
C5 C27B C28B C29B -103(3) . . . . ?
C5 C27B C29B C28B 108(3) . . . . ?
C35 C30 C31 C32 -0.8(4) . . . . ?
S1 C30 C31 C32 179.39(19) . . . . ?
C30 C31 C32 C33 0.9(4) . . . . ?
C31 C32 C33 C34 -0.2(4) . . . . ?
C31 C32 C33 C36 179.4(3) . . . . ?
C32 C33 C34 C35 -0.5(4) . . . . ?
C36 C33 C34 C35 179.9(3) . . . . ?
C31 C30 C35 C34 0.2(4) . . . . ?
S1 C30 C35 C34 179.9(2) . . . . ?
C33 C34 C35 C30 0.6(4) . . . . ?
C10 C11 O1 C14 -1.1(4) . . . . ?
C12 C11 O1 C14 178.9(3) . . . . ?
C22 C21 P1 O2 -159.1(2) . . . . ?
C26 C21 P1 O2 18.8(2) . . . . ?
C22 C21 P1 C15 -37.2(2) . . . . ?
C26 C21 P1 C15 140.7(2) . . . . ?
C22 C21 P1 C2 76.0(2) . . . . ?
C26 C21 P1 C2 -106.1(2) . . . . ?
C20 C15 P1 O2 4.5(2) . . . . ?
C16 C15 P1 O2 -172.5(2) . . . . ?
C20 C15 P1 C21 -115.59(19) . . . . ?
C16 C15 P1 C21 67.4(2) . . . . ?
C20 C15 P1 C2 127.04(18) . . . . ?
C16 C15 P1 C2 -49.9(2) . . . . ?
C4 C2 P1 O2 -168.41(16) . . . . ?
C3 C2 P1 O2 -19.0(2) . . . . ?
C1 C2 P1 O2 46.9(2) . . . . ?
C4 C2 P1 C21 -46.18(19) . . . . ?
C3 C2 P1 C21 103.18(19) . . . . ?
C1 C2 P1 C21 169.11(16) . . . . ?
C4 C2 P1 C15 70.22(18) . . . . ?
C3 C2 P1 C15 -140.42(18) . . . . ?
C1 C2 P1 C15 -74.48(18) . . . . ?
C35 C30 S1 O3 135.1(2) . . . . ?
C31 C30 S1 O3 -45.1(2) . . . . ?
C35 C30 S1 O4 5.9(2) . . . . ?
C31 C30 S1 O4 -174.34(19) . . . . ?
C35 C30 S1 C6 -110.1(2) . . . . ?
C31 C30 S1 C6 69.7(2) . . . . ?
C5 C6 S1 O3 -70.6(2) . . . . ?
C5 C6 S1 O4 59.2(2) . . . . ?
C5 C6 S1 C30 173.74(17) . . . . ?

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
C14 H14C O2 0.96 2.41 3.203(4) 139.7 4_466

_refine_diff_density_max         0.286
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.039



####################################################################### 
# 
# 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_CYZ170418_a
_database_code_depnum_ccdc_archive 'CCDC 1573907'
_audit_update_record             
;
2017-09-12 deposited with the CCDC.
2018-11-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
"(E)-(1-(2-([1,1'-biphenyl]-4-yl)-3-tosylprop-1-en-1-yl)-2-(4-methoxyphenyl)-2-methylcyclopropyl)diphenylphosphine oxide"
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C45 H41 O4 P S'
_chemical_formula_sum            'C45 H41 O4 P S'
_chemical_formula_weight         708.81

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.2440(3)
_cell_length_b                   13.1272(5)
_cell_length_c                   15.4443(5)
_cell_angle_alpha                85.2160(10)
_cell_angle_beta                 77.3190(10)
_cell_angle_gamma                69.9810(10)
_cell_volume                     1903.71(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9962
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      26.48

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_F_000             748
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.170
_shelx_estimated_absorpt_T_min   0.959
_shelx_estimated_absorpt_T_max   0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6811
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29840
_diffrn_reflns_av_unetI/netI     0.0439
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.143
_diffrn_reflns_theta_max         27.518
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             8679
_reflns_number_gt                5631
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0630P)²+0.3722P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8679
_refine_ls_number_parameters     463
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0945
_refine_ls_R_factor_gt           0.0539
_refine_ls_wR_factor_ref         0.1402
_refine_ls_wR_factor_gt          0.1232
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.82584(19) 0.47477(14) 0.14560(11) 0.0482(4) Uani 1 1 d . . . . .
C2 C 0.7525(2) 0.58792(15) 0.11670(11) 0.0529(5) Uani 1 1 d . . . . .
H2A H 0.6558 0.6055 0.1088 0.063 Uiso 1 1 calc R U . . .
H2B H 0.8091 0.6234 0.0748 0.063 Uiso 1 1 calc R U . . .
C3 C 0.77778(18) 0.57088(13) 0.21107(10) 0.0417(4) Uani 1 1 d . . . . .
C4 C 0.66088(18) 0.57164(13) 0.28788(10) 0.0426(4) Uani 1 1 d . . . . .
H4 H 0.6892 0.5278 0.3355 0.051 Uiso 1 1 calc R U . . .
C5 C 0.52215(18) 0.62514(14) 0.29929(11) 0.0449(4) Uani 1 1 d . . . . .
C6 C 0.4260(2) 0.59524(17) 0.37882(13) 0.0604(5) Uani 1 1 d . . . . .
H6A H 0.4755 0.5225 0.3976 0.072 Uiso 1 1 calc R U . . .
H6B H 0.3429 0.5930 0.3598 0.072 Uiso 1 1 calc R U . . .
C7 C 0.9821(2) 0.41772(16) 0.10716(14) 0.0633(5) Uani 1 1 d . . . . .
H7A H 1.0221 0.3625 0.1479 0.095 Uiso 1 1 calc R U . . .
H7B H 1.0313 0.4694 0.0977 0.095 Uiso 1 1 calc R U . . .
H7C H 0.9917 0.3852 0.0517 0.095 Uiso 1 1 calc R U . . .
C8 C 0.7416(2) 0.39891(15) 0.16128(13) 0.0543(5) Uani 1 1 d . . . . .
C9 C 0.6679(3) 0.3902(2) 0.09894(17) 0.0793(7) Uani 1 1 d . . . . .
H9 H 0.6691 0.4335 0.0481 0.095 Uiso 1 1 calc R U . . .
C10 C 0.5922(3) 0.3185(2) 0.1099(2) 0.0971(9) Uani 1 1 d . . . . .
H10 H 0.5450 0.3133 0.0663 0.117 Uiso 1 1 calc R U . . .
C11 C 0.5875(3) 0.2561(2) 0.1845(3) 0.0909(9) Uani 1 1 d . . . . .
C12 C 0.6611(3) 0.26151(18) 0.2461(2) 0.0818(7) Uani 1 1 d . . . . .
H12 H 0.6593 0.2176 0.2965 0.098 Uiso 1 1 calc R U . . .
C13 C 0.7388(2) 0.33137(15) 0.23498(15) 0.0633(5) Uani 1 1 d . . . . .
H13 H 0.7898 0.3329 0.2775 0.076 Uiso 1 1 calc R U . . .
C14 C 0.4154(4) 0.1896(3) 0.1465(4) 0.184(2) Uani 1 1 d . . . . .
H14A H 0.3507 0.2623 0.1444 0.276 Uiso 1 1 calc R U . . .
H14B H 0.3629 0.1415 0.1691 0.276 Uiso 1 1 calc R U . . .
H14C H 0.4689 0.1678 0.0878 0.276 Uiso 1 1 calc R U . . .
C15 C 1.02555(19) 0.52082(15) 0.29302(13) 0.0534(5) Uani 1 1 d . . . . .
C16 C 0.9782(2) 0.47129(18) 0.37051(15) 0.0690(6) Uani 1 1 d . . . . .
H16 H 0.8813 0.4882 0.3927 0.083 Uiso 1 1 calc R U . . .
C17 C 1.0735(3) 0.3971(2) 0.41509(18) 0.0845(7) Uani 1 1 d . . . . .
H17 H 1.0407 0.3641 0.4669 0.101 Uiso 1 1 calc R U . . .
C18 C 1.2160(3) 0.3724(2) 0.3832(2) 0.0922(8) Uani 1 1 d . . . . .
H18 H 1.2802 0.3235 0.4139 0.111 Uiso 1 1 calc R U . . .
C19 C 1.2641(3) 0.4195(2) 0.3060(2) 0.0907(8) Uani 1 1 d . . . . .
H19 H 1.3611 0.4021 0.2842 0.109 Uiso 1 1 calc R U . . .
C20 C 1.1702(2) 0.49203(18) 0.26075(16) 0.0683(6) Uani 1 1 d . . . . .
H20 H 1.2042 0.5222 0.2077 0.082 Uiso 1 1 calc R U . . .
C21 C 0.82767(19) 0.74294(15) 0.29379(13) 0.0501(4) Uani 1 1 d . . . . .
C22 C 0.8217(2) 0.83974(16) 0.24809(15) 0.0633(5) Uani 1 1 d . . . . .
H22 H 0.8650 0.8384 0.1884 0.076 Uiso 1 1 calc R U . . .
C23 C 0.7520(3) 0.93777(18) 0.29063(19) 0.0794(7) Uani 1 1 d . . . . .
H23 H 0.7451 1.0022 0.2589 0.095 Uiso 1 1 calc R U . . .
C24 C 0.6934(3) 0.9404(2) 0.3789(2) 0.0828(7) Uani 1 1 d . . . . .
H24 H 0.6482 1.0066 0.4077 0.099 Uiso 1 1 calc R U . . .
C25 C 0.7010(3) 0.8460(2) 0.42508(17) 0.0812(7) Uani 1 1 d . . . . .
H25 H 0.6617 0.8482 0.4855 0.097 Uiso 1 1 calc R U . . .
C26 C 0.7665(2) 0.74733(18) 0.38299(14) 0.0656(6) Uani 1 1 d . . . . .
H26 H 0.7695 0.6835 0.4149 0.079 Uiso 1 1 calc R U . . .
C27 C 0.2712(2) 0.8103(2) 0.43645(13) 0.0665(6) Uani 1 1 d . . . . .
C28 C 0.1375(3) 0.8310(3) 0.4211(2) 0.1039(9) Uani 1 1 d . . . . .
H28 H 0.0948 0.7778 0.4317 0.125 Uiso 1 1 calc R U . . .
C29 C 0.0671(3) 0.9322(3) 0.3895(2) 0.1204(11) Uani 1 1 d . . . . .
H29 H -0.0238 0.9460 0.3797 0.144 Uiso 1 1 calc R U . . .
C30 C 0.1255(4) 1.0126(3) 0.37222(18) 0.0987(9) Uani 1 1 d . . . . .
C31 C 0.2574(4) 0.9902(2) 0.38751(19) 0.0999(9) Uani 1 1 d . . . . .
H31 H 0.2998 1.0436 0.3766 0.120 Uiso 1 1 calc R U . . .
C32 C 0.3310(3) 0.8899(2) 0.41899(17) 0.0867(7) Uani 1 1 d . . . . .
H32 H 0.4221 0.8767 0.4283 0.104 Uiso 1 1 calc R U . . .
C33 C 0.0446(4) 1.1213(3) 0.3366(2) 0.1483(16) Uani 1 1 d . . . . .
H33A H 0.0538 1.1782 0.3674 0.222 Uiso 1 1 calc R U . . .
H33B H -0.0538 1.1284 0.3453 0.222 Uiso 1 1 calc R U . . .
H33C H 0.0824 1.1264 0.2744 0.222 Uiso 1 1 calc R U . . .
C34 C 0.45105(18) 0.71017(14) 0.23883(11) 0.0443(4) Uani 1 1 d . . . . .
C35 C 0.3334(2) 0.70688(18) 0.21068(15) 0.0717(6) Uani 1 1 d . . . . .
H35 H 0.3027 0.6477 0.2264 0.086 Uiso 1 1 calc R U . . .
C36 C 0.2606(2) 0.78887(18) 0.16001(14) 0.0665(6) Uani 1 1 d . . . . .
H36 H 0.1828 0.7833 0.1415 0.080 Uiso 1 1 calc R U . . .
C37 C 0.42269(19) 0.87987(15) 0.16076(13) 0.0530(5) Uani 1 1 d . . . . .
H37 H 0.4561 0.9374 0.1427 0.064 Uiso 1 1 calc R U . . .
C38 C 0.49551(19) 0.79743(14) 0.21121(12) 0.0512(5) Uani 1 1 d . . . . .
H38 H 0.5765 0.8008 0.2269 0.061 Uiso 1 1 calc R U . . .
C39 C 0.30070(18) 0.87913(14) 0.13618(11) 0.0452(4) Uani 1 1 d . . . . .
C40 C 0.21456(19) 0.97364(14) 0.09053(11) 0.0477(4) Uani 1 1 d . . . . .
C41 C 0.0679(2) 1.00849(19) 0.11317(14) 0.0691(6) Uani 1 1 d . . . . .
H41 H 0.0230 0.9705 0.1559 0.083 Uiso 1 1 calc R U . . .
C42 C -0.0132(3) 1.0995(2) 0.07286(16) 0.0817(7) Uani 1 1 d . . . . .
H42 H -0.1117 1.1220 0.0889 0.098 Uiso 1 1 calc R U . . .
C43 C 0.0505(3) 1.15591(18) 0.01014(17) 0.0773(7) Uani 1 1 d . . . . .
H43 H -0.0043 1.2164 -0.0171 0.093 Uiso 1 1 calc R U . . .
C44 C 0.1941(3) 1.12378(19) -0.01271(18) 0.0808(7) Uani 1 1 d . . . . .
H44 H 0.2379 1.1629 -0.0550 0.097 Uiso 1 1 calc R U . . .
C45 C 0.2754(2) 1.03302(17) 0.02679(14) 0.0642(5) Uani 1 1 d . . . . .
H45 H 0.3738 1.0114 0.0099 0.077 Uiso 1 1 calc R U . . .
O1 O 1.00109(15) 0.64539(11) 0.14416(9) 0.0683(4) Uani 1 1 d . . . . .
O2 O 0.5106(2) 0.18548(16) 0.2037(2) 0.1364(9) Uani 1 1 d . . . . .
O3 O 0.27069(18) 0.64085(17) 0.53589(10) 0.1042(6) Uani 1 1 d . . . . .
O4 O 0.48863(17) 0.68870(16) 0.50016(10) 0.0932(6) Uani 1 1 d . . . . .
P1 P 0.91523(5) 0.62074(4) 0.22843(3) 0.04930(15) Uani 1 1 d . . . . .
S1 S 0.36733(6) 0.68138(5) 0.47282(3) 0.0731(2) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.497(2) . ?
C1 C8 1.501(3) . ?
C1 C7 1.521(3) . ?
C1 C3 1.557(2) . ?
C2 C3 1.521(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.487(2) . ?
C3 P1 1.8190(18) . ?
C4 C5 1.331(2) . ?
C4 H4 0.9300 . ?
C5 C34 1.489(2) . ?
C5 C6 1.512(2) . ?
C6 S1 1.781(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.380(3) . ?
C8 C13 1.385(3) . ?
C9 C10 1.389(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.359(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.357(4) . ?
C11 O2 1.386(3) . ?
C12 C13 1.385(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 O2 1.438(5) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C20 1.383(3) . ?
C15 C16 1.386(3) . ?
C15 P1 1.804(2) . ?
C16 C17 1.381(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.365(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.369(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.370(3) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C26 1.380(3) . ?
C21 C22 1.390(3) . ?
C21 P1 1.8123(19) . ?
C22 C23 1.380(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.361(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.365(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.380(3) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 C32 1.364(3) . ?
C27 C28 1.372(3) . ?
C27 S1 1.759(2) . ?
C28 C29 1.383(4) . ?
C28 H28 0.9300 . ?
C29 C30 1.362(4) . ?
C29 H29 0.9300 . ?
C30 C31 1.351(4) . ?
C30 C33 1.512(4) . ?
C31 C32 1.383(4) . ?
C31 H31 0.9300 . ?
C32 H32 0.9300 . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C34 C38 1.375(2) . ?
C34 C35 1.382(3) . ?
C35 C36 1.376(3) . ?
C35 H35 0.9300 . ?
C36 C39 1.379(3) . ?
C36 H36 0.9300 . ?
C37 C38 1.377(2) . ?
C37 C39 1.387(2) . ?
C37 H37 0.9300 . ?
C38 H38 0.9300 . ?
C39 C40 1.481(2) . ?
C40 C45 1.379(3) . ?
C40 C41 1.384(3) . ?
C41 C42 1.389(3) . ?
C41 H41 0.9300 . ?
C42 C43 1.358(3) . ?
C42 H42 0.9300 . ?
C43 C44 1.356(4) . ?
C43 H43 0.9300 . ?
C44 C45 1.381(3) . ?
C44 H44 0.9300 . ?
C45 H45 0.9300 . ?
O1 P1 1.4812(13) . ?
O3 S1 1.4362(16) . ?
O4 S1 1.4318(17) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C8 116.71(16) . . ?
C2 C1 C7 120.27(16) . . ?
C8 C1 C7 112.49(15) . . ?
C2 C1 C3 59.68(11) . . ?
C8 C1 C3 117.18(14) . . ?
C7 C1 C3 121.05(16) . . ?
C1 C2 C3 62.12(11) . . ?
C1 C2 H2A 117.5 . . ?
C3 C2 H2A 117.5 . . ?
C1 C2 H2B 117.5 . . ?
C3 C2 H2B 117.5 . . ?
H2A C2 H2B 114.6 . . ?
C4 C3 C2 121.23(15) . . ?
C4 C3 C1 115.98(14) . . ?
C2 C3 C1 58.20(11) . . ?
C4 C3 P1 117.86(12) . . ?
C2 C3 P1 113.41(12) . . ?
C1 C3 P1 116.60(12) . . ?
C5 C4 C3 130.24(15) . . ?
C5 C4 H4 114.9 . . ?
C3 C4 H4 114.9 . . ?
C4 C5 C34 125.87(15) . . ?
C4 C5 C6 117.83(15) . . ?
C34 C5 C6 116.27(15) . . ?
C5 C6 S1 117.03(15) . . ?
C5 C6 H6A 108.0 . . ?
S1 C6 H6A 108.0 . . ?
C5 C6 H6B 108.0 . . ?
S1 C6 H6B 108.0 . . ?
H6A C6 H6B 107.3 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C13 116.9(2) . . ?
C9 C8 C1 120.25(19) . . ?
C13 C8 C1 122.76(19) . . ?
C8 C9 C10 121.9(3) . . ?
C8 C9 H9 119.1 . . ?
C10 C9 H9 119.1 . . ?
C11 C10 C9 119.7(3) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C12 C11 C10 119.7(3) . . ?
C12 C11 O2 116.0(3) . . ?
C10 C11 O2 124.4(3) . . ?
C11 C12 C13 121.0(3) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C8 C13 C12 120.8(2) . . ?
C8 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
O2 C14 H14A 109.5 . . ?
O2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C20 C15 C16 118.18(19) . . ?
C20 C15 P1 115.80(16) . . ?
C16 C15 P1 126.02(15) . . ?
C17 C16 C15 120.7(2) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C18 C17 C16 120.0(3) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C19 119.9(2) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
C18 C19 C20 120.5(2) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C19 C20 C15 120.7(2) . . ?
C19 C20 H20 119.6 . . ?
C15 C20 H20 119.6 . . ?
C26 C21 C22 118.44(19) . . ?
C26 C21 P1 125.79(15) . . ?
C22 C21 P1 115.77(15) . . ?
C23 C22 C21 120.5(2) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C24 C23 C22 120.2(2) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C23 C24 C25 120.0(2) . . ?
C23 C24 H24 120.0 . . ?
C25 C24 H24 120.0 . . ?
C24 C25 C26 120.6(2) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
C21 C26 C25 120.3(2) . . ?
C21 C26 H26 119.9 . . ?
C25 C26 H26 119.9 . . ?
C32 C27 C28 118.8(2) . . ?
C32 C27 S1 120.41(18) . . ?
C28 C27 S1 120.7(2) . . ?
C27 C28 C29 119.0(3) . . ?
C27 C28 H28 120.5 . . ?
C29 C28 H28 120.5 . . ?
C30 C29 C28 122.7(3) . . ?
C30 C29 H29 118.6 . . ?
C28 C29 H29 118.6 . . ?
C31 C30 C29 117.2(3) . . ?
C31 C30 C33 122.3(4) . . ?
C29 C30 C33 120.5(3) . . ?
C30 C31 C32 121.7(3) . . ?
C30 C31 H31 119.1 . . ?
C32 C31 H31 119.1 . . ?
C27 C32 C31 120.5(3) . . ?
C27 C32 H32 119.7 . . ?
C31 C32 H32 119.7 . . ?
C30 C33 H33A 109.5 . . ?
C30 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C30 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C38 C34 C35 116.97(16) . . ?
C38 C34 C5 121.82(16) . . ?
C35 C34 C5 121.16(16) . . ?
C36 C35 C34 121.79(18) . . ?
C36 C35 H35 119.1 . . ?
C34 C35 H35 119.1 . . ?
C35 C36 C39 121.23(18) . . ?
C35 C36 H36 119.4 . . ?
C39 C36 H36 119.4 . . ?
C38 C37 C39 121.55(17) . . ?
C38 C37 H37 119.2 . . ?
C39 C37 H37 119.2 . . ?
C34 C38 C37 121.42(17) . . ?
C34 C38 H38 119.3 . . ?
C37 C38 H38 119.3 . . ?
C36 C39 C37 116.87(16) . . ?
C36 C39 C40 122.03(16) . . ?
C37 C39 C40 121.04(16) . . ?
C45 C40 C41 117.13(17) . . ?
C45 C40 C39 122.17(16) . . ?
C41 C40 C39 120.66(17) . . ?
C40 C41 C42 120.8(2) . . ?
C40 C41 H41 119.6 . . ?
C42 C41 H41 119.6 . . ?
C43 C42 C41 120.4(2) . . ?
C43 C42 H42 119.8 . . ?
C41 C42 H42 119.8 . . ?
C44 C43 C42 119.9(2) . . ?
C44 C43 H43 120.1 . . ?
C42 C43 H43 120.1 . . ?
C43 C44 C45 120.1(2) . . ?
C43 C44 H44 120.0 . . ?
C45 C44 H44 120.0 . . ?
C40 C45 C44 121.7(2) . . ?
C40 C45 H45 119.1 . . ?
C44 C45 H45 119.1 . . ?
C11 O2 C14 117.2(3) . . ?
O1 P1 C15 111.04(9) . . ?
O1 P1 C21 109.49(8) . . ?
C15 P1 C21 108.00(9) . . ?
O1 P1 C3 112.71(8) . . ?
C15 P1 C3 108.13(8) . . ?
C21 P1 C3 107.29(8) . . ?
O4 S1 O3 118.01(11) . . ?
O4 S1 C27 108.54(12) . . ?
O3 S1 C27 108.29(11) . . ?
O4 S1 C6 108.93(10) . . ?
O3 S1 C6 106.29(11) . . ?
C27 S1 C6 106.18(9) . . ?

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
C8 C1 C2 C3 107.35(17) . . . . ?
C7 C1 C2 C3 -110.52(19) . . . . ?
C1 C2 C3 C4 -103.10(17) . . . . ?
C1 C2 C3 P1 107.80(14) . . . . ?
C2 C1 C3 C4 112.12(17) . . . . ?
C8 C1 C3 C4 5.6(2) . . . . ?
C7 C1 C3 C4 -138.64(17) . . . . ?
C8 C1 C3 C2 -106.55(19) . . . . ?
C7 C1 C3 C2 109.24(19) . . . . ?
C2 C1 C3 P1 -102.26(14) . . . . ?
C8 C1 C3 P1 151.19(14) . . . . ?
C7 C1 C3 P1 7.0(2) . . . . ?
C2 C3 C4 C5 -30.6(3) . . . . ?
C1 C3 C4 C5 -97.6(2) . . . . ?
P1 C3 C4 C5 117.21(19) . . . . ?
C3 C4 C5 C34 -7.8(3) . . . . ?
C3 C4 C5 C6 170.02(18) . . . . ?
C4 C5 C6 S1 100.25(19) . . . . ?
C34 C5 C6 S1 -81.74(19) . . . . ?
C2 C1 C8 C9 48.5(2) . . . . ?
C7 C1 C8 C9 -96.5(2) . . . . ?
C3 C1 C8 C9 116.4(2) . . . . ?
C2 C1 C8 C13 -134.77(18) . . . . ?
C7 C1 C8 C13 80.2(2) . . . . ?
C3 C1 C8 C13 -66.9(2) . . . . ?
C13 C8 C9 C10 1.1(3) . . . . ?
C1 C8 C9 C10 178.1(2) . . . . ?
C8 C9 C10 C11 1.2(4) . . . . ?
C9 C10 C11 C12 -2.4(4) . . . . ?
C9 C10 C11 O2 177.3(2) . . . . ?
C10 C11 C12 C13 1.3(4) . . . . ?
O2 C11 C12 C13 -178.39(19) . . . . ?
C9 C8 C13 C12 -2.2(3) . . . . ?
C1 C8 C13 C12 -179.08(17) . . . . ?
C11 C12 C13 C8 1.1(3) . . . . ?
C20 C15 C16 C17 1.5(3) . . . . ?
P1 C15 C16 C17 -178.78(18) . . . . ?
C15 C16 C17 C18 0.3(4) . . . . ?
C16 C17 C18 C19 -1.3(4) . . . . ?
C17 C18 C19 C20 0.4(4) . . . . ?
C18 C19 C20 C15 1.5(4) . . . . ?
C16 C15 C20 C19 -2.4(3) . . . . ?
P1 C15 C20 C19 177.86(18) . . . . ?
C26 C21 C22 C23 -2.1(3) . . . . ?
P1 C21 C22 C23 177.18(16) . . . . ?
C21 C22 C23 C24 2.7(3) . . . . ?
C22 C23 C24 C25 -1.3(4) . . . . ?
C23 C24 C25 C26 -0.7(4) . . . . ?
C22 C21 C26 C25 0.1(3) . . . . ?
P1 C21 C26 C25 -179.07(17) . . . . ?
C24 C25 C26 C21 1.2(4) . . . . ?
C32 C27 C28 C29 -0.8(4) . . . . ?
S1 C27 C28 C29 -177.7(2) . . . . ?
C27 C28 C29 C30 0.5(5) . . . . ?
C28 C29 C30 C31 -0.3(5) . . . . ?
C28 C29 C30 C33 179.2(3) . . . . ?
C29 C30 C31 C32 0.3(4) . . . . ?
C33 C30 C31 C32 -179.1(3) . . . . ?
C28 C27 C32 C31 0.9(4) . . . . ?
S1 C27 C32 C31 177.79(19) . . . . ?
C30 C31 C32 C27 -0.6(4) . . . . ?
C4 C5 C34 C38 -51.3(3) . . . . ?
C6 C5 C34 C38 130.92(19) . . . . ?
C4 C5 C34 C35 131.3(2) . . . . ?
C6 C5 C34 C35 -46.5(3) . . . . ?
C38 C34 C35 C36 -2.3(3) . . . . ?
C5 C34 C35 C36 175.3(2) . . . . ?
C34 C35 C36 C39 -1.0(4) . . . . ?
C35 C34 C38 C37 2.5(3) . . . . ?
C5 C34 C38 C37 -175.04(17) . . . . ?
C39 C37 C38 C34 0.6(3) . . . . ?
C35 C36 C39 C37 4.0(3) . . . . ?
C35 C36 C39 C40 -172.9(2) . . . . ?
C38 C37 C39 C36 -3.8(3) . . . . ?
C38 C37 C39 C40 173.18(17) . . . . ?
C36 C39 C40 C45 -144.2(2) . . . . ?
C37 C39 C40 C45 38.9(3) . . . . ?
C36 C39 C40 C41 38.3(3) . . . . ?
C37 C39 C40 C41 -138.5(2) . . . . ?
C45 C40 C41 C42 0.0(3) . . . . ?
C39 C40 C41 C42 177.56(19) . . . . ?
C40 C41 C42 C43 0.2(4) . . . . ?
C41 C42 C43 C44 -0.6(4) . . . . ?
C42 C43 C44 C45 0.9(4) . . . . ?
C41 C40 C45 C44 0.3(3) . . . . ?
C39 C40 C45 C44 -177.2(2) . . . . ?
C43 C44 C45 C40 -0.8(4) . . . . ?
C12 C11 O2 C14 171.1(3) . . . . ?
C10 C11 O2 C14 -8.6(4) . . . . ?
C20 C15 P1 O1 6.90(18) . . . . ?
C16 C15 P1 O1 -172.85(18) . . . . ?
C20 C15 P1 C21 -113.16(16) . . . . ?
C16 C15 P1 C21 67.1(2) . . . . ?
C20 C15 P1 C3 131.04(15) . . . . ?
C16 C15 P1 C3 -48.7(2) . . . . ?
C26 C21 P1 O1 -164.07(17) . . . . ?
C22 C21 P1 O1 16.71(17) . . . . ?
C26 C21 P1 C15 -43.04(19) . . . . ?
C22 C21 P1 C15 137.74(15) . . . . ?
C26 C21 P1 C3 73.32(19) . . . . ?
C22 C21 P1 C3 -105.91(15) . . . . ?
C4 C3 P1 O1 -163.67(12) . . . . ?
C2 C3 P1 O1 -13.45(15) . . . . ?
C1 C3 P1 O1 51.37(14) . . . . ?
C4 C3 P1 C15 73.20(14) . . . . ?
C2 C3 P1 C15 -136.59(13) . . . . ?
C1 C3 P1 C15 -71.76(14) . . . . ?
C4 C3 P1 C21 -43.07(14) . . . . ?
C2 C3 P1 C21 107.15(13) . . . . ?
C1 C3 P1 C21 171.97(12) . . . . ?
C32 C27 S1 O4 14.5(2) . . . . ?
C28 C27 S1 O4 -168.6(2) . . . . ?
C32 C27 S1 O3 143.8(2) . . . . ?
C28 C27 S1 O3 -39.4(2) . . . . ?
C32 C27 S1 C6 -102.4(2) . . . . ?
C28 C27 S1 C6 74.4(2) . . . . ?
C5 C6 S1 O4 -55.96(17) . . . . ?
C5 C6 S1 O3 175.91(14) . . . . ?
C5 C6 S1 C27 60.75(17) . . . . ?

_refine_diff_density_max         0.179
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.036



####################################################################### 
# 
# 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_CYZ170802
_database_code_depnum_ccdc_archive 'CCDC 1573912'
_audit_update_record             
;
2017-09-12 deposited with the CCDC.
2018-11-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'(E)-(2,2-dibenzyl-1-(2-methyl-3-tosylprop-1-en-1-yl)cyclopropyl)diphenylphosphine oxide'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C40 H39 O3 P S'
_chemical_formula_sum            'C40 H39 O3 P S'
_chemical_formula_weight         630.74

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   10.9576(5)
_cell_length_b                   24.0001(11)
_cell_length_c                   13.0509(6)
_cell_angle_alpha                90
_cell_angle_beta                 94.036(2)
_cell_angle_gamma                90
_cell_volume                     3423.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9990
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      27.14

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_F_000             1336
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.178
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6804
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            39323
_diffrn_reflns_av_unetI/netI     0.0449
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.521
_diffrn_reflns_theta_max         27.526
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             7858
_reflns_number_gt                4897
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0593P)²+0.6904P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7858
_refine_ls_number_parameters     408
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0969
_refine_ls_R_factor_gt           0.0501
_refine_ls_wR_factor_ref         0.1315
_refine_ls_wR_factor_gt          0.1136
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.77768(17) 0.61866(7) 0.38234(13) 0.0452(4) Uani 1 1 d . . . . .
C2 C 0.66107(16) 0.65272(7) 0.40042(13) 0.0424(4) Uani 1 1 d . . . . .
C3 C 0.65591(17) 0.59941(8) 0.33706(14) 0.0518(5) Uani 1 1 d . . . . .
H3A H 0.6205 0.5667 0.3669 0.062 Uiso 1 1 calc R U . . .
H3B H 0.6395 0.6029 0.2633 0.062 Uiso 1 1 calc R U . . .
C4 C 0.61760(17) 0.65148(7) 0.50670(13) 0.0421(4) Uani 1 1 d . . . . .
H4 H 0.6706 0.6663 0.5584 0.051 Uiso 1 1 calc R U . . .
C5 C 0.51230(17) 0.63168(7) 0.53556(13) 0.0441(4) Uani 1 1 d . . . . .
C6 C 0.49138(17) 0.63168(8) 0.64831(13) 0.0477(4) Uani 1 1 d . . . . .
H6A H 0.4048 0.6363 0.6573 0.057 Uiso 1 1 calc R U . . .
H6B H 0.5348 0.6627 0.6817 0.057 Uiso 1 1 calc R U . . .
C7 C 0.41086(19) 0.60788(10) 0.46589(16) 0.0649(6) Uani 1 1 d . . . . .
H7A H 0.4298 0.6125 0.3957 0.097 Uiso 1 1 calc R U . . .
H7B H 0.3359 0.6269 0.4770 0.097 Uiso 1 1 calc R U . . .
H7C H 0.4019 0.5689 0.4804 0.097 Uiso 1 1 calc R U . . .
C8 C 0.83189(17) 0.58399(7) 0.47208(14) 0.0500(5) Uani 1 1 d . . . . .
H8A H 0.7667 0.5754 0.5162 0.060 Uiso 1 1 calc R U . . .
H8B H 0.8596 0.5489 0.4449 0.060 Uiso 1 1 calc R U . . .
C9 C 0.93620(16) 0.60896(8) 0.53767(14) 0.0476(4) Uani 1 1 d . . . . .
C10 C 0.95187(19) 0.66545(9) 0.55124(15) 0.0579(5) Uani 1 1 d . . . . .
H10 H 0.8953 0.6899 0.5193 0.070 Uiso 1 1 calc R U . . .
C11 C 1.0497(2) 0.68660(11) 0.61129(18) 0.0723(6) Uani 1 1 d . . . . .
H11 H 1.0586 0.7249 0.6192 0.087 Uiso 1 1 calc R U . . .
C12 C 1.1337(2) 0.65146(14) 0.6592(2) 0.0847(8) Uani 1 1 d . . . . .
H12 H 1.1998 0.6657 0.6995 0.102 Uiso 1 1 calc R U . . .
C13 C 1.1196(2) 0.59529(14) 0.6474(2) 0.0875(8) Uani 1 1 d . . . . .
H13 H 1.1762 0.5711 0.6799 0.105 Uiso 1 1 calc R U . . .
C14 C 1.0218(2) 0.57427(10) 0.58741(17) 0.0672(6) Uani 1 1 d . . . . .
H14 H 1.0133 0.5359 0.5802 0.081 Uiso 1 1 calc R U . . .
C15 C 0.86966(18) 0.64001(8) 0.30900(14) 0.0525(5) Uani 1 1 d . . . . .
H15A H 0.8261 0.6593 0.2523 0.063 Uiso 1 1 calc R U . . .
H15B H 0.9240 0.6666 0.3449 0.063 Uiso 1 1 calc R U . . .
C16 C 0.94472(18) 0.59360(8) 0.26724(15) 0.0515(5) Uani 1 1 d . . . . .
C17 C 0.8987(2) 0.56014(9) 0.18808(17) 0.0641(6) Uani 1 1 d . . . . .
H17 H 0.8205 0.5668 0.1580 0.077 Uiso 1 1 calc R U . . .
C18 C 0.9680(2) 0.51643(10) 0.1526(2) 0.0817(7) Uani 1 1 d . . . . .
H18 H 0.9363 0.4943 0.0986 0.098 Uiso 1 1 calc R U . . .
C19 C 1.0830(2) 0.50596(11) 0.1972(2) 0.0809(7) Uani 1 1 d . . . . .
H19 H 1.1287 0.4765 0.1741 0.097 Uiso 1 1 calc R U . . .
C20 C 1.1297(2) 0.53867(11) 0.2749(2) 0.0757(7) Uani 1 1 d . . . . .
H20 H 1.2075 0.5316 0.3053 0.091 Uiso 1 1 calc R U . . .
C21 C 1.06189(19) 0.58243(10) 0.30915(16) 0.0642(6) Uani 1 1 d . . . . .
H21 H 1.0956 0.6050 0.3617 0.077 Uiso 1 1 calc R U . . .
C22 C 0.73307(17) 0.76854(7) 0.37732(14) 0.0454(4) Uani 1 1 d . . . . .
C23 C 0.75487(19) 0.78112(8) 0.48162(14) 0.0517(5) Uani 1 1 d . . . . .
H23 H 0.7108 0.7630 0.5300 0.062 Uiso 1 1 calc R U . . .
C24 C 0.8411(2) 0.82013(9) 0.51261(17) 0.0651(6) Uani 1 1 d . . . . .
H24 H 0.8558 0.8279 0.5822 0.078 Uiso 1 1 calc R U . . .
C25 C 0.9061(2) 0.84794(10) 0.4418(2) 0.0756(7) Uani 1 1 d . . . . .
H25 H 0.9642 0.8744 0.4637 0.091 Uiso 1 1 calc R U . . .
C26 C 0.8849(2) 0.83656(10) 0.3394(2) 0.0737(7) Uani 1 1 d . . . . .
H26 H 0.9281 0.8556 0.2916 0.088 Uiso 1 1 calc R U . . .
C27 C 0.80004(19) 0.79707(8) 0.30687(16) 0.0576(5) Uani 1 1 d . . . . .
H27 H 0.7871 0.7893 0.2371 0.069 Uiso 1 1 calc R U . . .
C28 C 0.47380(18) 0.73573(8) 0.35530(15) 0.0538(5) Uani 1 1 d . . . . .
C29 C 0.3824(2) 0.72171(11) 0.28192(19) 0.0793(7) Uani 1 1 d . . . . .
H29 H 0.4026 0.7066 0.2197 0.095 Uiso 1 1 calc R U . . .
C30 C 0.2604(3) 0.72993(14) 0.2999(3) 0.1004(9) Uani 1 1 d . . . . .
H30 H 0.1992 0.7190 0.2509 0.120 Uiso 1 1 calc R U . . .
C31 C 0.2299(3) 0.75397(14) 0.3894(3) 0.1032(10) Uani 1 1 d . . . . .
H31 H 0.1482 0.7597 0.4013 0.124 Uiso 1 1 calc R U . . .
C32 C 0.3200(3) 0.76957(12) 0.4614(2) 0.0939(8) Uani 1 1 d . . . . .
H32 H 0.2993 0.7866 0.5218 0.113 Uiso 1 1 calc R U . . .
C33 C 0.4410(2) 0.76026(10) 0.44529(19) 0.0713(6) Uani 1 1 d . . . . .
H33 H 0.5014 0.7705 0.4954 0.086 Uiso 1 1 calc R U . . .
C34 C 0.49747(19) 0.57101(8) 0.83210(14) 0.0520(5) Uani 1 1 d . . . . .
C35 C 0.3882(2) 0.54734(11) 0.85519(18) 0.0771(7) Uani 1 1 d . . . . .
H35 H 0.3388 0.5295 0.8045 0.093 Uiso 1 1 calc R U . . .
C36 C 0.3532(2) 0.55046(12) 0.95377(18) 0.0820(8) Uani 1 1 d . . . . .
H36 H 0.2795 0.5344 0.9691 0.098 Uiso 1 1 calc R U . . .
C37 C 0.42360(19) 0.57661(9) 1.03085(16) 0.0612(6) Uani 1 1 d . . . . .
C38 C 0.5328(2) 0.59953(9) 1.00629(16) 0.0646(6) Uani 1 1 d . . . . .
H38 H 0.5822 0.6174 1.0571 0.078 Uiso 1 1 calc R U . . .
C39 C 0.57024(19) 0.59661(9) 0.90820(15) 0.0590(5) Uani 1 1 d . . . . .
H39 H 0.6449 0.6120 0.8933 0.071 Uiso 1 1 calc R U . . .
C40 C 0.3821(3) 0.57970(13) 1.13805(18) 0.0921(8) Uani 1 1 d . . . . .
H40A H 0.4365 0.6034 1.1791 0.138 Uiso 1 1 calc R U . . .
H40B H 0.3828 0.5430 1.1675 0.138 Uiso 1 1 calc R U . . .
H40C H 0.3007 0.5946 1.1360 0.138 Uiso 1 1 calc R U . . .
O1 O 0.63483(14) 0.70892(6) 0.21478(9) 0.0631(4) Uani 1 1 d . . . . .
O2 O 0.67498(16) 0.56871(8) 0.70983(12) 0.0969(6) Uani 1 1 d . . . . .
O3 O 0.4791(2) 0.52400(7) 0.65388(13) 0.1155(8) Uani 1 1 d . . . . .
P1 P 0.62761(5) 0.71613(2) 0.32712(3) 0.04701(15) Uani 1 1 d . . . . .
S1 S 0.54369(6) 0.56806(2) 0.70572(4) 0.06213(18) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C3 1.494(3) . ?
C1 C8 1.523(2) . ?
C1 C15 1.527(3) . ?
C1 C2 1.549(2) . ?
C2 C4 1.498(2) . ?
C2 C3 1.522(2) . ?
C2 P1 1.8212(17) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.327(2) . ?
C4 H4 0.9300 . ?
C5 C7 1.499(3) . ?
C5 C6 1.505(2) . ?
C6 S1 1.7780(18) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.503(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.376(3) . ?
C9 C14 1.382(3) . ?
C10 C11 1.380(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.367(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.365(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.377(3) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.509(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.376(3) . ?
C16 C21 1.386(3) . ?
C17 C18 1.393(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.374(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.354(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.379(3) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C27 1.396(3) . ?
C22 C23 1.398(2) . ?
C22 P1 1.8000(19) . ?
C23 C24 1.371(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.378(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.368(3) . ?
C25 H25 0.9300 . ?
C26 C27 1.374(3) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 C29 1.378(3) . ?
C28 C33 1.383(3) . ?
C28 P1 1.812(2) . ?
C29 C30 1.388(4) . ?
C29 H29 0.9300 . ?
C30 C31 1.365(4) . ?
C30 H30 0.9300 . ?
C31 C32 1.366(4) . ?
C31 H31 0.9300 . ?
C32 C33 1.376(3) . ?
C32 H32 0.9300 . ?
C33 H33 0.9300 . ?
C34 C39 1.374(3) . ?
C34 C35 1.378(3) . ?
C34 S1 1.761(2) . ?
C35 C36 1.370(3) . ?
C35 H35 0.9300 . ?
C36 C37 1.375(3) . ?
C36 H36 0.9300 . ?
C37 C38 1.375(3) . ?
C37 C40 1.503(3) . ?
C38 C39 1.373(3) . ?
C38 H38 0.9300 . ?
C39 H39 0.9300 . ?
C40 H40A 0.9600 . ?
C40 H40B 0.9600 . ?
C40 H40C 0.9600 . ?
O1 P1 1.4839(13) . ?
O2 S1 1.4359(18) . ?
O3 S1 1.4176(18) . ?

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
C3 C1 C8 115.12(15) . . ?
C3 C1 C15 117.80(16) . . ?
C8 C1 C15 115.25(16) . . ?
C3 C1 C2 60.00(12) . . ?
C8 C1 C2 116.90(15) . . ?
C15 C1 C2 120.44(15) . . ?
C4 C2 C3 118.96(15) . . ?
C4 C2 C1 116.75(14) . . ?
C3 C2 C1 58.21(11) . . ?
C4 C2 P1 115.94(12) . . ?
C3 C2 P1 114.75(12) . . ?
C1 C2 P1 119.92(12) . . ?
C1 C3 C2 61.79(12) . . ?
C1 C3 H3A 117.6 . . ?
C2 C3 H3A 117.6 . . ?
C1 C3 H3B 117.6 . . ?
C2 C3 H3B 117.6 . . ?
H3A C3 H3B 114.7 . . ?
C5 C4 C2 127.55(16) . . ?
C5 C4 H4 116.2 . . ?
C2 C4 H4 116.2 . . ?
C4 C5 C7 125.94(17) . . ?
C4 C5 C6 118.22(16) . . ?
C7 C5 C6 115.83(16) . . ?
C5 C6 S1 110.19(13) . . ?
C5 C6 H6A 109.6 . . ?
S1 C6 H6A 109.6 . . ?
C5 C6 H6B 109.6 . . ?
S1 C6 H6B 109.6 . . ?
H6A C6 H6B 108.1 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C1 117.38(15) . . ?
C9 C8 H8A 108.0 . . ?
C1 C8 H8A 108.0 . . ?
C9 C8 H8B 108.0 . . ?
C1 C8 H8B 108.0 . . ?
H8A C8 H8B 107.2 . . ?
C10 C9 C14 117.29(19) . . ?
C10 C9 C8 123.28(17) . . ?
C14 C9 C8 119.43(18) . . ?
C9 C10 C11 121.4(2) . . ?
C9 C10 H10 119.3 . . ?
C11 C10 H10 119.3 . . ?
C12 C11 C10 120.3(2) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C13 C12 C11 119.3(2) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C12 C13 C14 120.3(2) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C13 C14 C9 121.4(2) . . ?
C13 C14 H14 119.3 . . ?
C9 C14 H14 119.3 . . ?
C16 C15 C1 112.30(15) . . ?
C16 C15 H15A 109.1 . . ?
C1 C15 H15A 109.1 . . ?
C16 C15 H15B 109.1 . . ?
C1 C15 H15B 109.1 . . ?
H15A C15 H15B 107.9 . . ?
C17 C16 C21 117.65(19) . . ?
C17 C16 C15 121.44(18) . . ?
C21 C16 C15 120.90(19) . . ?
C16 C17 C18 120.6(2) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C19 C18 C17 120.1(2) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C20 C19 C18 119.9(2) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C20 C21 120.0(2) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C20 C21 C16 121.7(2) . . ?
C20 C21 H21 119.2 . . ?
C16 C21 H21 119.2 . . ?
C27 C22 C23 118.27(18) . . ?
C27 C22 P1 117.19(15) . . ?
C23 C22 P1 124.50(14) . . ?
C24 C23 C22 120.11(18) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C23 C24 C25 120.7(2) . . ?
C23 C24 H24 119.6 . . ?
C25 C24 H24 119.6 . . ?
C26 C25 C24 119.9(2) . . ?
C26 C25 H25 120.1 . . ?
C24 C25 H25 120.1 . . ?
C25 C26 C27 120.3(2) . . ?
C25 C26 H26 119.8 . . ?
C27 C26 H26 119.8 . . ?
C26 C27 C22 120.7(2) . . ?
C26 C27 H27 119.7 . . ?
C22 C27 H27 119.7 . . ?
C29 C28 C33 118.3(2) . . ?
C29 C28 P1 115.89(17) . . ?
C33 C28 P1 125.68(16) . . ?
C28 C29 C30 120.7(3) . . ?
C28 C29 H29 119.7 . . ?
C30 C29 H29 119.7 . . ?
C31 C30 C29 120.1(3) . . ?
C31 C30 H30 120.0 . . ?
C29 C30 H30 120.0 . . ?
C30 C31 C32 119.8(3) . . ?
C30 C31 H31 120.1 . . ?
C32 C31 H31 120.1 . . ?
C31 C32 C33 120.5(3) . . ?
C31 C32 H32 119.7 . . ?
C33 C32 H32 119.7 . . ?
C32 C33 C28 120.6(2) . . ?
C32 C33 H33 119.7 . . ?
C28 C33 H33 119.7 . . ?
C39 C34 C35 119.70(19) . . ?
C39 C34 S1 120.30(16) . . ?
C35 C34 S1 120.00(16) . . ?
C36 C35 C34 119.2(2) . . ?
C36 C35 H35 120.4 . . ?
C34 C35 H35 120.4 . . ?
C35 C36 C37 122.2(2) . . ?
C35 C36 H36 118.9 . . ?
C37 C36 H36 118.9 . . ?
C36 C37 C38 117.7(2) . . ?
C36 C37 C40 120.9(2) . . ?
C38 C37 C40 121.5(2) . . ?
C39 C38 C37 121.26(19) . . ?
C39 C38 H38 119.4 . . ?
C37 C38 H38 119.4 . . ?
C38 C39 C34 120.01(19) . . ?
C38 C39 H39 120.0 . . ?
C34 C39 H39 120.0 . . ?
C37 C40 H40A 109.5 . . ?
C37 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C37 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
O1 P1 C22 111.32(8) . . ?
O1 P1 C28 110.23(9) . . ?
C22 P1 C28 109.10(9) . . ?
O1 P1 C2 113.50(8) . . ?
C22 P1 C2 107.00(8) . . ?
C28 P1 C2 105.43(8) . . ?
O3 S1 O2 119.42(14) . . ?
O3 S1 C34 108.07(11) . . ?
O2 S1 C34 108.54(10) . . ?
O3 S1 C6 107.72(11) . . ?
O2 S1 C6 107.39(10) . . ?
C34 S1 C6 104.76(9) . . ?

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
C3 C1 C2 C4 109.00(17) . . . . ?
C8 C1 C2 C4 4.1(2) . . . . ?
C15 C1 C2 C4 -144.41(17) . . . . ?
C8 C1 C2 C3 -104.87(18) . . . . ?
C15 C1 C2 C3 106.59(19) . . . . ?
C3 C1 C2 P1 -102.21(15) . . . . ?
C8 C1 C2 P1 152.91(13) . . . . ?
C15 C1 C2 P1 4.4(2) . . . . ?
C8 C1 C3 C2 107.84(17) . . . . ?
C15 C1 C3 C2 -110.91(17) . . . . ?
C4 C2 C3 C1 -105.20(17) . . . . ?
P1 C2 C3 C1 111.13(14) . . . . ?
C3 C2 C4 C5 -50.4(3) . . . . ?
C1 C2 C4 C5 -117.2(2) . . . . ?
P1 C2 C4 C5 92.8(2) . . . . ?
C2 C4 C5 C7 -2.5(3) . . . . ?
C2 C4 C5 C6 176.33(16) . . . . ?
C4 C5 C6 S1 -90.22(18) . . . . ?
C7 C5 C6 S1 88.73(18) . . . . ?
C3 C1 C8 C9 -164.63(15) . . . . ?
C15 C1 C8 C9 53.1(2) . . . . ?
C2 C1 C8 C9 -97.04(19) . . . . ?
C1 C8 C9 C10 28.4(3) . . . . ?
C1 C8 C9 C14 -151.52(18) . . . . ?
C14 C9 C10 C11 0.6(3) . . . . ?
C8 C9 C10 C11 -179.31(19) . . . . ?
C9 C10 C11 C12 -0.2(3) . . . . ?
C10 C11 C12 C13 -0.2(4) . . . . ?
C11 C12 C13 C14 0.2(4) . . . . ?
C12 C13 C14 C9 0.2(4) . . . . ?
C10 C9 C14 C13 -0.6(3) . . . . ?
C8 C9 C14 C13 179.3(2) . . . . ?
C3 C1 C15 C16 -86.2(2) . . . . ?
C8 C1 C15 C16 55.0(2) . . . . ?
C2 C1 C15 C16 -156.01(16) . . . . ?
C1 C15 C16 C17 79.3(2) . . . . ?
C1 C15 C16 C21 -99.2(2) . . . . ?
C21 C16 C17 C18 0.5(3) . . . . ?
C15 C16 C17 C18 -178.1(2) . . . . ?
C16 C17 C18 C19 0.6(4) . . . . ?
C17 C18 C19 C20 -0.9(4) . . . . ?
C18 C19 C20 C21 -0.1(4) . . . . ?
C19 C20 C21 C16 1.3(4) . . . . ?
C17 C16 C21 C20 -1.5(3) . . . . ?
C15 C16 C21 C20 177.12(19) . . . . ?
C27 C22 C23 C24 -0.7(3) . . . . ?
P1 C22 C23 C24 177.13(15) . . . . ?
C22 C23 C24 C25 0.9(3) . . . . ?
C23 C24 C25 C26 -0.1(4) . . . . ?
C24 C25 C26 C27 -0.7(4) . . . . ?
C25 C26 C27 C22 0.9(3) . . . . ?
C23 C22 C27 C26 -0.2(3) . . . . ?
P1 C22 C27 C26 -178.15(17) . . . . ?
C33 C28 C29 C30 -2.6(4) . . . . ?
P1 C28 C29 C30 173.8(2) . . . . ?
C28 C29 C30 C31 2.4(4) . . . . ?
C29 C30 C31 C32 -0.4(5) . . . . ?
C30 C31 C32 C33 -1.3(5) . . . . ?
C31 C32 C33 C28 1.0(4) . . . . ?
C29 C28 C33 C32 0.9(3) . . . . ?
P1 C28 C33 C32 -175.1(2) . . . . ?
C39 C34 C35 C36 0.9(4) . . . . ?
S1 C34 C35 C36 -179.4(2) . . . . ?
C34 C35 C36 C37 0.1(4) . . . . ?
C35 C36 C37 C38 -0.7(4) . . . . ?
C35 C36 C37 C40 179.5(3) . . . . ?
C36 C37 C38 C39 0.2(3) . . . . ?
C40 C37 C38 C39 -180.0(2) . . . . ?
C37 C38 C39 C34 0.8(3) . . . . ?
C35 C34 C39 C38 -1.4(3) . . . . ?
S1 C34 C39 C38 178.98(17) . . . . ?
C27 C22 P1 O1 3.73(17) . . . . ?
C23 C22 P1 O1 -174.13(15) . . . . ?
C27 C22 P1 C28 -118.14(15) . . . . ?
C23 C22 P1 C28 64.00(18) . . . . ?
C27 C22 P1 C2 128.26(15) . . . . ?
C23 C22 P1 C2 -49.59(18) . . . . ?
C29 C28 P1 O1 22.60(19) . . . . ?
C33 C28 P1 O1 -161.26(18) . . . . ?
C29 C28 P1 C22 145.13(16) . . . . ?
C33 C28 P1 C22 -38.7(2) . . . . ?
C29 C28 P1 C2 -100.26(17) . . . . ?
C33 C28 P1 C2 75.9(2) . . . . ?
C4 C2 P1 O1 -161.16(13) . . . . ?
C3 C2 P1 O1 -16.36(16) . . . . ?
C1 C2 P1 O1 49.81(16) . . . . ?
C4 C2 P1 C22 75.65(15) . . . . ?
C3 C2 P1 C22 -139.55(13) . . . . ?
C1 C2 P1 C22 -73.38(15) . . . . ?
C4 C2 P1 C28 -40.42(15) . . . . ?
C3 C2 P1 C28 104.39(14) . . . . ?
C1 C2 P1 C28 170.56(14) . . . . ?
C39 C34 S1 O3 159.10(18) . . . . ?
C35 C34 S1 O3 -20.6(2) . . . . ?
C39 C34 S1 O2 28.2(2) . . . . ?
C35 C34 S1 O2 -151.45(19) . . . . ?
C39 C34 S1 C6 -86.26(18) . . . . ?
C35 C34 S1 C6 94.08(19) . . . . ?
C5 C6 S1 O3 -58.55(17) . . . . ?
C5 C6 S1 O2 71.26(16) . . . . ?
C5 C6 S1 C34 -173.45(13) . . . . ?

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
C3 H3A O3 0.97 2.44 3.317(3) 150.0 3_666

_refine_diff_density_max         0.194
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.037



####################################################################### 
# 
# 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_NJAU_CYZ_001
_database_code_depnum_ccdc_archive 'CCDC 1573911'
_audit_update_record             
;
2017-09-12 deposited with the CCDC.
2018-11-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'(E)-(2-methyl-1-(2-methyl-3-tosylprop-1-en-1-yl)-2-(naphthalen-2-yl)cyclopropyl)diphenylphosphine oxide'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C37 H35 O3 P S'
_chemical_formula_sum            'C37 H35 O3 P S'
_chemical_formula_weight         590.68

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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   12.3705(6)
_cell_length_b                   13.8788(8)
_cell_length_c                   19.1238(10)
_cell_angle_alpha                90
_cell_angle_beta                 106.7020(10)
_cell_angle_gamma                90
_cell_volume                     3144.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9961
_cell_measurement_theta_min      2.260
_cell_measurement_theta_max      27.128

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_F_000             1248
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.280
_exptl_absorpt_coefficient_mu    0.189
_shelx_estimated_absorpt_T_min   0.937
_shelx_estimated_absorpt_T_max   0.949
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.930
_exptl_absorpt_correction_T_max  0.955
_exptl_absorpt_process_details   '(SADABS; Bruker, 2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30918
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.260
_diffrn_reflns_theta_max         27.509
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             7092
_reflns_number_gt                5114
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0536P)²+0.9790P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7092
_refine_ls_number_parameters     370
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0729
_refine_ls_R_factor_gt           0.0464
_refine_ls_wR_factor_ref         0.1237
_refine_ls_wR_factor_gt          0.1122
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.49775(14) 0.23544(12) 0.63762(9) 0.0362(4) Uani 1 1 d . . . . .
C2 C 0.43792(15) 0.15364(13) 0.58594(10) 0.0444(4) Uani 1 1 d . . . . .
C3 C 0.39265(16) 0.18552(14) 0.64672(10) 0.0480(5) Uani 1 1 d . . . . .
H3A H 0.4023 0.1424 0.6879 0.058 Uiso 1 1 calc R U . . .
H3B H 0.3226 0.2218 0.6339 0.058 Uiso 1 1 calc R U . . .
C4 C 0.37468(16) 0.18200(13) 0.50935(10) 0.0460(4) Uani 1 1 d . . . . .
C5 C 0.25966(17) 0.18030(14) 0.48559(11) 0.0540(5) Uani 1 1 d . . . . .
H5 H 0.2198 0.1629 0.5181 0.065 Uiso 1 1 calc R U . . .
C6 C 0.19922(18) 0.20420(15) 0.41305(12) 0.0586(6) Uani 1 1 d . . . . .
C7 C 0.0794(2) 0.20350(18) 0.38782(16) 0.0815(8) Uani 1 1 d . . . . .
H7 H 0.0381 0.1862 0.4195 0.098 Uiso 1 1 calc R U . . .
C8 C 0.0246(3) 0.2279(2) 0.3177(2) 0.0983(11) Uani 1 1 d . . . . .
H8 H -0.0539 0.2269 0.3018 0.118 Uiso 1 1 calc R U . . .
C9 C 0.0846(3) 0.2543(2) 0.26959(18) 0.1042(11) Uani 1 1 d . . . . .
H9 H 0.0459 0.2713 0.2219 0.125 Uiso 1 1 calc R U . . .
C10 C 0.1988(3) 0.25571(19) 0.29114(14) 0.0859(8) Uani 1 1 d . . . . .
H10 H 0.2376 0.2733 0.2581 0.103 Uiso 1 1 calc R U . . .
C11 C 0.2602(2) 0.23048(16) 0.36385(12) 0.0641(6) Uani 1 1 d . . . . .
C12 C 0.3787(2) 0.23076(17) 0.38885(12) 0.0657(6) Uani 1 1 d . . . . .
H12 H 0.4199 0.2474 0.3569 0.079 Uiso 1 1 calc R U . . .
C13 C 0.43409(18) 0.20705(15) 0.45925(11) 0.0557(5) Uani 1 1 d . . . . .
H13 H 0.5126 0.2074 0.4745 0.067 Uiso 1 1 calc R U . . .
C14 C 0.49115(19) 0.05458(14) 0.59070(12) 0.0578(5) Uani 1 1 d . . . . .
H14A H 0.5287 0.0396 0.6408 0.087 Uiso 1 1 calc R U . . .
H14B H 0.5449 0.0539 0.5631 0.087 Uiso 1 1 calc R U . . .
H14C H 0.4336 0.0075 0.5712 0.087 Uiso 1 1 calc R U . . .
C15 C 0.48761(13) 0.33642(12) 0.60980(8) 0.0338(4) Uani 1 1 d . . . . .
H15 H 0.5071 0.3482 0.5671 0.041 Uiso 1 1 calc R U . . .
C16 C 0.45296(13) 0.41068(12) 0.64131(8) 0.0343(4) Uani 1 1 d . . . . .
C17 C 0.41649(17) 0.40428(14) 0.70971(10) 0.0494(5) Uani 1 1 d . . . . .
H17A H 0.3396 0.4253 0.6995 0.074 Uiso 1 1 calc R U . . .
H17B H 0.4640 0.4446 0.7467 0.074 Uiso 1 1 calc R U . . .
H17C H 0.4225 0.3388 0.7265 0.074 Uiso 1 1 calc R U . . .
C18 C 0.45443(14) 0.51096(12) 0.61116(9) 0.0378(4) Uani 1 1 d . . . . .
H18A H 0.5237 0.5192 0.5977 0.045 Uiso 1 1 calc R U . . .
H18B H 0.4556 0.5570 0.6495 0.045 Uiso 1 1 calc R U . . .
C19 C 0.21786(14) 0.50511(13) 0.55924(9) 0.0390(4) Uani 1 1 d . . . . .
C20 C 0.16822(16) 0.57048(15) 0.59449(11) 0.0516(5) Uani 1 1 d . . . . .
H20 H 0.1971 0.6325 0.6042 0.062 Uiso 1 1 calc R U . . .
C21 C 0.07504(17) 0.54248(17) 0.61519(11) 0.0583(5) Uani 1 1 d . . . . .
H21 H 0.0404 0.5869 0.6382 0.070 Uiso 1 1 calc R U . . .
C22 C 0.03236(16) 0.45160(17) 0.60291(11) 0.0542(5) Uani 1 1 d . . . . .
C23 C 0.08287(18) 0.38742(17) 0.56745(13) 0.0644(6) Uani 1 1 d . . . . .
H23 H 0.0543 0.3252 0.5585 0.077 Uiso 1 1 calc R U . . .
C24 C 0.17520(17) 0.41340(15) 0.54486(12) 0.0552(5) Uani 1 1 d . . . . .
H24 H 0.2080 0.3696 0.5203 0.066 Uiso 1 1 calc R U . . .
C25 C -0.06873(19) 0.4235(2) 0.62743(15) 0.0867(9) Uani 1 1 d . . . . .
H25A H -0.1020 0.3661 0.6023 0.130 Uiso 1 1 calc R U . . .
H25B H -0.1231 0.4748 0.6165 0.130 Uiso 1 1 calc R U . . .
H25C H -0.0454 0.4118 0.6791 0.130 Uiso 1 1 calc R U . . .
C26 C 0.68610(10) 0.31706(8) 0.75418(6) 0.0434(4) Uani 1 1 d G . . . .
C27 C 0.72498(11) 0.39157(9) 0.71924(6) 0.0534(5) Uani 1 1 d G . . . .
H27 H 0.7196 0.3867 0.6699 0.064 Uiso 1 1 calc R U . . .
C28 C 0.77192(12) 0.47342(8) 0.75811(10) 0.0752(7) Uani 1 1 d G . . . .
H28 H 0.7979 0.5233 0.7347 0.090 Uiso 1 1 calc R U . . .
C29 C 0.77998(13) 0.48075(10) 0.83193(9) 0.0870(9) Uani 1 1 d G . . . .
H29 H 0.8114 0.5355 0.8579 0.104 Uiso 1 1 calc R U . . .
C30 C 0.74109(14) 0.40623(12) 0.86687(6) 0.0844(9) Uani 1 1 d G . . . .
H30 H 0.7465 0.4111 0.9163 0.101 Uiso 1 1 calc R U . . .
C31 C 0.69415(12) 0.32439(10) 0.82799(6) 0.0604(6) Uani 1 1 d G . . . .
H31 H 0.6681 0.2745 0.8514 0.072 Uiso 1 1 calc R U . . .
C32 C 0.72764(15) 0.16177(13) 0.66465(9) 0.0435(4) Uani 1 1 d . . . . .
C33 C 0.7907(2) 0.08097(15) 0.69398(12) 0.0629(6) Uani 1 1 d . . . . .
H33 H 0.7814 0.0522 0.7358 0.076 Uiso 1 1 calc R U . . .
C34 C 0.8671(2) 0.04344(19) 0.66126(16) 0.0854(8) Uani 1 1 d . . . . .
H34 H 0.9090 -0.0109 0.6808 0.102 Uiso 1 1 calc R U . . .
C35 C 0.8816(2) 0.0860(2) 0.59983(17) 0.0864(8) Uani 1 1 d . . . . .
H35 H 0.9334 0.0605 0.5780 0.104 Uiso 1 1 calc R U . . .
C36 C 0.8203(2) 0.16562(19) 0.57045(13) 0.0720(7) Uani 1 1 d . . . . .
H36 H 0.8307 0.1943 0.5289 0.086 Uiso 1 1 calc R U . . .
C37 C 0.74295(17) 0.20339(15) 0.60240(11) 0.0524(5) Uani 1 1 d . . . . .
H37 H 0.7008 0.2572 0.5820 0.063 Uiso 1 1 calc R U . . .
O1 O 0.34435(12) 0.47859(14) 0.47429(7) 0.0726(5) Uani 1 1 d . . . . .
O2 O 0.33734(12) 0.64093(11) 0.52506(9) 0.0737(5) Uani 1 1 d . . . . .
O3 O 0.60832(13) 0.13634(10) 0.76285(7) 0.0599(4) Uani 1 1 d . . . . .
P1 P 0.62687(4) 0.20608(3) 0.70901(2) 0.04010(13) Uani 1 1 d . . . . .
S1 S 0.33871(4) 0.53831(4) 0.53429(3) 0.04815(14) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C15 1.491(2) . ?
C1 C3 1.527(2) . ?
C1 C2 1.547(2) . ?
C1 P1 1.8243(17) . ?
C2 C3 1.495(3) . ?
C2 C4 1.501(3) . ?
C2 C14 1.516(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.364(3) . ?
C4 C13 1.408(3) . ?
C5 C6 1.413(3) . ?
C5 H5 0.9300 . ?
C6 C11 1.413(3) . ?
C6 C7 1.420(3) . ?
C7 C8 1.361(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.387(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.354(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.423(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.405(3) . ?
C12 C13 1.364(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.326(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.504(2) . ?
C16 C18 1.509(2) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 S1 1.7733(17) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C24 1.375(3) . ?
C19 C20 1.376(3) . ?
C19 S1 1.7564(17) . ?
C20 C21 1.378(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.361(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.374(3) . ?
C22 C25 1.507(3) . ?
C23 C24 1.380(3) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 C27 1.3900 . ?
C26 C31 1.3900 . ?
C26 P1 1.8143(10) . ?
C27 C28 1.3900 . ?
C27 H27 0.9300 . ?
C28 C29 1.3900 . ?
C28 H28 0.9300 . ?
C29 C30 1.3900 . ?
C29 H29 0.9300 . ?
C30 C31 1.3900 . ?
C30 H30 0.9300 . ?
C31 H31 0.9300 . ?
C32 C37 1.384(3) . ?
C32 C33 1.389(3) . ?
C32 P1 1.8054(19) . ?
C33 C34 1.377(3) . ?
C33 H33 0.9300 . ?
C34 C35 1.371(4) . ?
C34 H34 0.9300 . ?
C35 C36 1.366(4) . ?
C35 H35 0.9300 . ?
C36 C37 1.378(3) . ?
C36 H36 0.9300 . ?
C37 H37 0.9300 . ?
O1 S1 1.4333(16) . ?
O2 S1 1.4346(16) . ?
O3 P1 1.4783(13) . ?

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
C15 C1 C3 118.69(15) . . ?
C15 C1 C2 119.08(14) . . ?
C3 C1 C2 58.19(11) . . ?
C15 C1 P1 116.28(11) . . ?
C3 C1 P1 113.86(12) . . ?
C2 C1 P1 117.99(12) . . ?
C3 C2 C4 118.32(16) . . ?
C3 C2 C14 118.37(16) . . ?
C4 C2 C14 113.08(15) . . ?
C3 C2 C1 60.23(11) . . ?
C4 C2 C1 116.76(15) . . ?
C14 C2 C1 120.50(16) . . ?
C2 C3 C1 61.58(11) . . ?
C2 C3 H3A 117.6 . . ?
C1 C3 H3A 117.6 . . ?
C2 C3 H3B 117.6 . . ?
C1 C3 H3B 117.6 . . ?
H3A C3 H3B 114.7 . . ?
C5 C4 C13 118.44(19) . . ?
C5 C4 C2 121.44(18) . . ?
C13 C4 C2 120.06(17) . . ?
C4 C5 C6 122.0(2) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
C11 C6 C5 118.8(2) . . ?
C11 C6 C7 118.7(2) . . ?
C5 C6 C7 122.5(2) . . ?
C8 C7 C6 120.6(3) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C9 120.6(3) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C10 C9 C8 120.9(3) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C11 120.7(3) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C12 C11 C6 118.6(2) . . ?
C12 C11 C10 122.9(3) . . ?
C6 C11 C10 118.5(2) . . ?
C13 C12 C11 121.0(2) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C12 C13 C4 121.2(2) . . ?
C12 C13 H13 119.4 . . ?
C4 C13 H13 119.4 . . ?
C2 C14 H14A 109.5 . . ?
C2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C1 124.99(15) . . ?
C16 C15 H15 117.5 . . ?
C1 C15 H15 117.5 . . ?
C15 C16 C17 124.50(15) . . ?
C15 C16 C18 120.17(14) . . ?
C17 C16 C18 115.25(14) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 S1 114.75(12) . . ?
C16 C18 H18A 108.6 . . ?
S1 C18 H18A 108.6 . . ?
C16 C18 H18B 108.6 . . ?
S1 C18 H18B 108.6 . . ?
H18A C18 H18B 107.6 . . ?
C24 C19 C20 120.57(17) . . ?
C24 C19 S1 119.75(14) . . ?
C20 C19 S1 119.66(15) . . ?
C19 C20 C21 118.88(19) . . ?
C19 C20 H20 120.6 . . ?
C21 C20 H20 120.6 . . ?
C22 C21 C20 121.78(19) . . ?
C22 C21 H21 119.1 . . ?
C20 C21 H21 119.1 . . ?
C21 C22 C23 118.49(19) . . ?
C21 C22 C25 120.1(2) . . ?
C23 C22 C25 121.4(2) . . ?
C22 C23 C24 121.3(2) . . ?
C22 C23 H23 119.3 . . ?
C24 C23 H23 119.3 . . ?
C19 C24 C23 118.94(19) . . ?
C19 C24 H24 120.5 . . ?
C23 C24 H24 120.5 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C27 C26 C31 120.0 . . ?
C27 C26 P1 123.43(7) . . ?
C31 C26 P1 116.55(7) . . ?
C26 C27 C28 120.0 . . ?
C26 C27 H27 120.0 . . ?
C28 C27 H27 120.0 . . ?
C27 C28 C29 120.0 . . ?
C27 C28 H28 120.0 . . ?
C29 C28 H28 120.0 . . ?
C30 C29 C28 120.0 . . ?
C30 C29 H29 120.0 . . ?
C28 C29 H29 120.0 . . ?
C31 C30 C29 120.0 . . ?
C31 C30 H30 120.0 . . ?
C29 C30 H30 120.0 . . ?
C30 C31 C26 120.0 . . ?
C30 C31 H31 120.0 . . ?
C26 C31 H31 120.0 . . ?
C37 C32 C33 118.96(19) . . ?
C37 C32 P1 123.06(14) . . ?
C33 C32 P1 117.96(15) . . ?
C34 C33 C32 120.1(2) . . ?
C34 C33 H33 120.0 . . ?
C32 C33 H33 120.0 . . ?
C35 C34 C33 120.1(2) . . ?
C35 C34 H34 120.0 . . ?
C33 C34 H34 120.0 . . ?
C36 C35 C34 120.5(2) . . ?
C36 C35 H35 119.8 . . ?
C34 C35 H35 119.8 . . ?
C35 C36 C37 119.9(2) . . ?
C35 C36 H36 120.0 . . ?
C37 C36 H36 120.0 . . ?
C36 C37 C32 120.4(2) . . ?
C36 C37 H37 119.8 . . ?
C32 C37 H37 119.8 . . ?
O3 P1 C32 111.76(9) . . ?
O3 P1 C26 110.27(7) . . ?
C32 P1 C26 105.90(7) . . ?
O3 P1 C1 112.94(8) . . ?
C32 P1 C1 107.38(8) . . ?
C26 P1 C1 108.27(7) . . ?
O1 S1 O2 118.50(10) . . ?
O1 S1 C19 107.87(9) . . ?
O2 S1 C19 108.24(9) . . ?
O1 S1 C18 109.05(9) . . ?
O2 S1 C18 107.02(9) . . ?
C19 S1 C18 105.43(8) . . ?

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
C3 H3A O3 0.97 2.54 3.018(2) 110 .
C18 H18A O1 0.97 2.42 3.350(2) 161 3_666
C18 H18B O3 0.97 2.33 3.242(2) 157 2_656
C37 H37 O2 0.93 2.42 3.195(2) 141 3_666

_refine_diff_density_max         0.238
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.039



