# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_compound23
_database_code_depnum_ccdc_archive 'CCDC 1818362'
_audit_update_record             
;
2018-01-21 deposited with the CCDC.
2018-04-24 downloaded from the CCDC.
;
#  internal code  phos3

#===============================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
"(1R,Rₚ)-(1',3',5'(10')-estratrien-3'-ylmethyl) ethyl (1-hydroxy-2-methylsulfanyl-1-phenylethyl)phosphonate"
_chemical_name_common            'compound 23'
_chemical_melting_point          383
# in K (in Celsius 108-112 deg C)
_chemical_formula_moiety         'C30 H41 O4 P S'
_chemical_formula_structural     ?
_chemical_formula_sum            'C30 H41 O4 P S'
_chemical_formula_iupac          ?
_chemical_formula_weight         528.66
_chemical_compound_source        'see text'

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'

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 2'
_symmetry_Int_Tables_number      5

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,y,-z
3 1/2+x,1/2+y,z
4 1/2-x,1/2+y,-z

_cell_length_a                   21.157(6)
_cell_length_b                   6.917(2)
_cell_length_c                   20.174(6)
_cell_angle_alpha                90
_cell_angle_beta                 98.00(3)
_cell_angle_gamma                90
_cell_volume                     2923.6(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    293
_cell_measurement_reflns_used    42
_cell_measurement_theta_min      6.00
_cell_measurement_theta_max      22.00
_cell_special_details            
;
;

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless

_exptl_crystal_size_max          0.850
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.070
_exptl_crystal_size_rad          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             1136
_exptl_absorpt_coefficient_mu    0.197
_exptl_crystal_density_meas_temp ?

_exptl_absorpt_correction_type   none

#===============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
; 
Philips PW1100 four-circle diffractometer with sealed X-ray tube,
graphite monochromator, and szintillation detector (point detector).
Reflection intensities were measured by theta-2theta scans 
with stationary background measurements on both sides of the scans.
;
_diffrn_ambient_temperature      293
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'Philips PW1100 four-circle diffractometer'
_diffrn_measurement_method       'θ--2θ scans'
_diffrn_standards_number         3
_diffrn_standards_interval_time  120
_diffrn_standards_decay_%        0.7

# number of measured reflections (redundant set)
_diffrn_reflns_number            2575
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_sigmaI/netI    0.0350
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.50
_diffrn_reflns_theta_max         24.00
_diffrn_reflns_theta_full        24.00
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_reduction_process 
;
;

# number of unique reflections
_reflns_number_total             2499
# number of observed reflections (> n sig(I))
_reflns_number_gt                2202
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Philips PW1100 (Philips AG, Eindhoven, 1973)'
_computing_cell_refinement       'Local software'
_computing_data_reduction        'Local software'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2006)'
_computing_publication_material  'PLATON (Spek, 2003)'

#===============================================================================

# 8. REFINEMENT DATA

_refine_special_details          
;
 Refinement on F² for ALL reflections except those
 flagged by the user for potential systematic errors.
 Weighted R-factors wR and all goodnesses of fit S
 are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The
 observed criterion of F² > 2sigma(F²) is used only
 for calculating -R-factor-obs etc. and is not
 relevant to the choice of reflections for refinement.
 R-factors based on F² are statistically about twice
 as large as those based on F, and R-factors based on
 ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0288P)²+0.0630P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom


_refine_ls_hydrogen_treatment    constr

_refine_ls_extinction_method     none
_refine_ls_abs_structure_details 
;
The absolute structure was fixed by the known absolute
configuration of the 1,3,5(10)-estratrien-3-ol used 
in the synthesis of the title compound.
;
_refine_ls_abs_structure_Flack   0.07(5)

# Permitted for _chemical_absolute_configuration:
# Absolute configuration details
# rm   = Det. by chiral ref. mol. with known abs.conf
# ad   = Det. by anomalous dispersion
# rmad = Det. by 'rm' and 'ad'
# syn  = Det. with reference to synthesis
# unk  = Unknown/Arbitrary
_chemical_absolute_configuration rm

_refine_ls_number_reflns         2496
_refine_ls_number_parameters     334
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0441
_refine_ls_wR_factor_ref         0.1197
_refine_ls_wR_factor_gt          0.1031
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.046

#===============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.0857(1) 0.7006(2) 0.0971(1) 0.056(1) Uani 1 1 d . . .
S1 S -0.0836(1) 0.4195(2) 0.1653(1) 0.079(1) Uani 1 1 d . . .
O1 O -0.0316(1) 0.8036(5) 0.0906(1) 0.059(1) Uani 1 1 d . . .
H1 H -0.0422 0.7436 0.0524 0.085 Uiso 1 1 calc R . .
O2 O 0.0798(1) 0.6335(6) 0.0276(1) 0.067(1) Uani 1 1 d . . .
O3 O 0.1343(1) 0.5842(6) 0.1474(1) 0.071(1) Uani 1 1 d . . .
O4 O 0.1096(2) 0.9138(6) 0.1072(2) 0.073(1) Uani 1 1 d . . .
C1 C 0.0104(2) 0.6806(7) 0.1325(2) 0.052(1) Uani 1 1 d . . .
C2 C -0.0130(2) 0.4712(8) 0.1274(2) 0.065(1) Uani 1 1 d . . .
H2A H -0.0215 0.4365 0.0804 0.078 Uiso 1 1 calc R . .
H2B H 0.0212 0.3886 0.1480 0.078 Uiso 1 1 calc R . .
C3 C -0.1468(2) 0.5218(12) 0.1091(3) 0.095(2) Uani 1 1 d . . .
H3A H -0.1866 0.5004 0.1258 0.143 Uiso 1 1 calc R . .
H3B H -0.1398 0.6582 0.1052 0.143 Uiso 1 1 calc R . .
H3C H -0.1482 0.4622 0.0659 0.143 Uiso 1 1 calc R . .
C4 C 0.0181(2) 0.7603(7) 0.2030(2) 0.054(1) Uani 1 1 d . . .
C5 C 0.0470(2) 0.6528(11) 0.2569(2) 0.076(2)^00 Uani 1 1 d . . .
H5 H 0.0624 0.5295 0.2501 0.092 Uiso 1 1 calc R . .
C6 C 0.0530(2) 0.7301(15) 0.3215(3) 0.095(2) Uani 1 1 d . . .
H6 H 0.0725 0.6585 0.3577 0.114 Uiso 1 1 calc R . .
C7 C 0.0303(3) 0.9102(17) 0.3312(3) 0.111(3) Uani 1 1 d . . .
H7 H 0.0341 0.9618 0.3741 0.141 Uiso 1 1 calc R . .
C8 C 0.0024(3) 1.0183(12) 0.2787(3) 0.096(2) Uani 1 1 d . . .
H8 H -0.0131 1.1412 0.2860 0.107 Uiso 1 1 calc R . .
C9 C -0.0038(2) 0.9424(10) 0.2147(2) 0.073(2) Uani 1 1 d . . .
H9 H -0.0229 1.0174 0.1792 0.087 Uiso 1 1 calc R . .
C10 C 0.2014(2) 0.5727(11) 0.1415(2) 0.083(2) Uani 1 1 d . . .
H10A H 0.2210 0.6987 0.1500 0.100 Uiso 1 1 calc R . .
H10B H 0.2067 0.5341 0.0964 0.100 Uiso 1 1 calc R . .
C11 C 0.3293(2) 0.3016(8) 0.2503(2) 0.061(1) Uani 1 1 d . . .
H11 H 0.3733 0.3103 0.2619 0.074 Uiso 1 1 calc R . .
C12 C 0.2985(2) 0.4360(9) 0.2073(2) 0.064(1) Uani 1 1 d . . .
H12 H 0.3221 0.5319 0.1896 0.077 Uiso 1 1 calc R . .
C13 C 0.2331(2) 0.4309(9) 0.1899(2) 0.062(1) Uani 1 1 d . . .
C14 C 0.2006(2) 0.2843(10) 0.2175(2) 0.073(2) Uani 1 1 d . . .
H14 H 0.1566 0.2769 0.2059 0.085 Uiso 1 1 calc R . .
C15 C 0.2301(2) 0.1500(8) 0.2609(2) 0.063(1) Uani 1 1 d . . .
C16 C 0.1894(2) -0.0002(10) 0.2905(2) 0.086(2) Uani 1 1 d . . .
H16A H 0.1585 -0.0516 0.2549 0.103 Uiso 1 1 calc R . .
H16B H 0.1659 0.0635 0.3223 0.103 Uiso 1 1 calc R . .
C17 C 0.2259(2) -0.1641(10) 0.3248(2) 0.078(2) Uani 1 1 d . . .
H17A H 0.2361 -0.2558 0.2915 0.094 Uiso 1 1 calc R . .
H17B H 0.1994 -0.2298 0.3533 0.094 Uiso 1 1 calc R . .
C18 C 0.2869(2) -0.0995(7) 0.3667(2) 0.054(1) Uani 1 1 d . . .
H18 H 0.2760 -0.0018 0.3984 0.064 Uiso 1 1 calc R . .
C19 C 0.3303(2) -0.0037(7) 0.3210(2) 0.056(1) Uani 1 1 d . . .
H19 H 0.3403 -0.1055 0.2903 0.068 Uiso 1 1 calc R . .
C20 C 0.2964(2) 0.1523(7) 0.2771(2) 0.052(1) Uani 1 1 d . . .
C21 C 0.3942(2) 0.0576(9) 0.3597(2) 0.073(2) Uani 1 1 d . . .
H21A H 0.3873 0.1650 0.3887 0.087 Uiso 1 1 calc R . .
H21B H 0.4218 0.1024 0.3283 0.087 Uiso 1 1 calc R . .
C22 C 0.4280(2) -0.1059(10) 0.4022(2) 0.079(2) Uani 1 1 d . . .
H22A H 0.4659 -0.0549 0.4291 0.095 Uiso 1 1 calc R . .
H22B H 0.4414 -0.2044 0.3729 0.095 Uiso 1 1 calc R . .
C23 C 0.3852(2) -0.1967(8) 0.4478(2) 0.061(1) Uani 1 1 d . . .
C24 C 0.3232(2) -0.2598(8) 0.4053(2) 0.062(1) Uani 1 1 d . . .
H24 H 0.3360 -0.3482 0.3716 0.074 Uiso 1 1 calc R . .
C25 C 0.2916(2) -0.3868(10) 0.4533(3) 0.087(2) Uani 1 1 d . . .
H25A H 0.2653 -0.4848 0.4286 0.104 Uiso 1 1 calc R . .
H25B H 0.2651 -0.3103 0.4789 0.104 Uiso 1 1 calc R . .
C26 C 0.3467(3) -0.4793(11) 0.4993(4) 0.103(2) Uani 1 1 d . . .
H26A H 0.3469 -0.6182 0.4927 0.124 Uiso 1 1 calc R . .
H26B H 0.3428 -0.4532 0.5458 0.124 Uiso 1 1 calc R . .
C27 C 0.4077(3) -0.3893(10) 0.4807(3) 0.088(2) Uani 1 1 d . . .
H27A H 0.4387 -0.3682 0.5202 0.106 Uiso 1 1 calc R . .
H27B H 0.4265 -0.4712 0.4497 0.106 Uiso 1 1 calc R . .
C28 C 0.3736(3) -0.0545(11) 0.5030(3) 0.087(2) Uani 1 1 d . . .
H28A H 0.3595 0.0671 0.4833 0.131 Uiso 1 1 calc R . .
H28B H 0.3415 -0.1056 0.5274 0.131 Uiso 1 1 calc R . .
H28C H 0.4126 -0.0358 0.5329 0.131 Uiso 1 1 calc R . .
C29 C 0.1041(3) 1.0565(10) 0.0532(3) 0.091(2) Uani 1 1 d . . .
H29A H 0.0927 1.1810 0.0702 0.109 Uiso 1 1 calc R . .
H29B H 0.0705 1.0179 0.0180 0.109 Uiso 1 1 calc R . .
C30 C 0.1630(4) 1.0734(15) 0.0263(4) 0.157(4) Uani 1 1 d . . .
H30A H 0.1584 1.1676 -0.0090 0.235 Uiso 1 1 calc R . .
H30B H 0.1962 1.1134 0.0610 0.235 Uiso 1 1 calc R . .
H30C H 0.1739 0.9506 0.0089 0.235 Uiso 1 1 calc R . .


#===============================================================================

# 10. MOLECULAR GEOMETRY

# 10. MOLECULAR GEOMETRY

_geom_special_details            
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C2 1.806(5) . . yes
S1 C3 1.775(6) . . yes
P1 O2 1.466(3) . . yes
P1 O3 1.564(3) . . yes
P1 O4 1.563(4) . . yes
P1 C1 1.840(5) . . yes
O1 C1 1.421(5) . . yes
O3 C10 1.443(5) . . yes
O4 C29 1.463(8) . . yes
O1 H1 0.8800 . . no
C1 C4 1.513(6) . . no
C1 C2 1.530(7) . . no
C4 C9 1.374(8) . . no
C4 C5 1.387(7) . . no
C5 C6 1.398(8) . . no
C6 C7 1.359(15) . . no
C7 C8 1.362(11) . . no
C8 C9 1.383(8) . . no
C10 C13 1.478(8) . . no
C11 C20 1.396(7) . . no
C11 C12 1.373(7) . . no
C12 C13 1.380(6) . . no
C13 C14 1.385(8) . . no
C14 C15 1.366(7) . . no
C15 C16 1.523(7) . . no
C15 C20 1.395(6) . . no
C16 C17 1.487(8) . . no
C17 C18 1.509(6) . . no
C18 C24 1.503(7) . . no
C18 C19 1.539(6) . . no
C19 C20 1.512(6) . . no
C19 C21 1.524(6) . . no
C21 C22 1.535(8) . . no
C22 C23 1.514(7) . . no
C23 C27 1.534(9) . . no
C23 C28 1.531(8) . . no
C23 C24 1.528(6) . . no
C24 C25 1.529(8) . . no
C25 C26 1.526(9) . . no
C26 C27 1.526(9) . . no
C29 C30 1.432(11) . . no
C2 H2A 0.9700 . . no
C2 H2B 0.9700 . . no
C3 H3A 0.9600 . . no
C3 H3B 0.9600 . . no
C3 H3C 0.9600 . . no
C5 H5 0.9300 . . no
C6 H6 0.9300 . . no
C7 H7 0.9300 . . no
C8 H8 0.9300 . . no
C9 H9 0.9300 . . no
C10 H10A 0.9700 . . no
C10 H10B 0.9700 . . no
C11 H11 0.9300 . . no
C12 H12 0.9300 . . no
C14 H14 0.9300 . . no
C16 H16A 0.9700 . . no
C16 H16B 0.9700 . . no
C17 H17A 0.9700 . . no
C17 H17B 0.9700 . . no
C18 H18 0.9800 . . no
C19 H19 0.9800 . . no
C21 H21A 0.9700 . . no
C21 H21B 0.9700 . . no
C22 H22A 0.9700 . . no
C22 H22B 0.9700 . . no
C24 H24 0.9800 . . no
C25 H25A 0.9700 . . no
C25 H25B 0.9700 . . no
C26 H26A 0.9700 . . no
C26 H26B 0.9700 . . no
C27 H27A 0.9700 . . no
C27 H27B 0.9700 . . no
C28 H28A 0.9600 . . no
C28 H28B 0.9600 . . no
C28 H28C 0.9600 . . no
C29 H29A 0.9700 . . no
C29 H29B 0.9700 . . no
C30 H30A 0.9600 . . no
C30 H30B 0.9600 . . no
C30 H30C 0.9600 . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 S1 C3 104.2(2) . . . yes
O2 P1 O3 114.7(2) . . . yes
O2 P1 O4 114.0(2) . . . yes
O2 P1 C1 112.6(2) . . . yes
O3 P1 O4 103.3(2) . . . yes
O3 P1 C1 103.7(2) . . . yes
O4 P1 C1 107.6(2) . . . yes
P1 O3 C10 122.7(3) . . . yes
P1 O4 C29 123.3(4) . . . yes
C1 O1 H1 108.00 . . . no
P1 C1 O1 103.2(3) . . . yes
P1 C1 C2 109.6(3) . . . yes
O1 C1 C2 110.9(3) . . . yes
O1 C1 C4 108.5(4) . . . yes
P1 C1 C4 110.6(3) . . . yes
C2 C1 C4 113.6(4) . . . no
S1 C2 C1 116.0(3) . . . yes
C1 C4 C9 120.1(4) . . . no
C5 C4 C9 118.6(4) . . . no
C1 C4 C5 121.3(5) . . . no
C4 C5 C6 119.9(7) . . . no
C5 C6 C7 119.8(6) . . . no
C6 C7 C8 121.0(7) . . . no
C7 C8 C9 119.5(8) . . . no
C4 C9 C8 121.2(5) . . . no
O3 C10 C13 110.1(4) . . . yes
C12 C11 C20 121.8(4) . . . no
C11 C12 C13 121.0(5) . . . no
C10 C13 C12 119.9(5) . . . no
C10 C13 C14 123.1(4) . . . no
C12 C13 C14 116.9(5) . . . no
C13 C14 C15 123.2(4) . . . no
C14 C15 C20 119.8(4) . . . no
C16 C15 C20 121.4(4) . . . no
C14 C15 C16 118.8(4) . . . no
C15 C16 C17 114.7(4) . . . no
C16 C17 C18 112.5(5) . . . no
C17 C18 C19 109.1(3) . . . no
C17 C18 C24 114.0(4) . . . no
C19 C18 C24 108.9(4) . . . no
C18 C19 C21 111.9(3) . . . no
C20 C19 C21 114.6(4) . . . no
C18 C19 C20 112.6(4) . . . no
C11 C20 C19 122.2(4) . . . no
C15 C20 C19 120.6(4) . . . no
C11 C20 C15 117.2(4) . . . no
C19 C21 C22 113.1(5) . . . no
C21 C22 C23 111.9(4) . . . no
C22 C23 C27 116.6(4) . . . no
C22 C23 C28 110.2(5) . . . no
C22 C23 C24 108.5(3) . . . no
C24 C23 C28 112.3(4) . . . no
C27 C23 C28 108.3(4) . . . no
C24 C23 C27 100.7(4) . . . no
C18 C24 C25 121.0(4) . . . no
C23 C24 C25 103.1(4) . . . no
C18 C24 C23 114.6(4) . . . no
C24 C25 C26 105.2(4) . . . no
C25 C26 C27 106.3(6) . . . no
C23 C27 C26 103.8(5) . . . no
O4 C29 C30 110.8(6) . . . yes
S1 C2 H2A 108.00 . . . no
S1 C2 H2B 108.00 . . . no
C1 C2 H2A 108.00 . . . no
C1 C2 H2B 108.00 . . . no
H2A C2 H2B 107.00 . . . no
S1 C3 H3A 109.00 . . . no
S1 C3 H3B 109.00 . . . no
S1 C3 H3C 109.00 . . . no
H3A C3 H3B 109.00 . . . no
H3A C3 H3C 110.00 . . . no
H3B C3 H3C 109.00 . . . no
C4 C5 H5 120.00 . . . no
C6 C5 H5 120.00 . . . no
C5 C6 H6 120.00 . . . no
C7 C6 H6 120.00 . . . no
C6 C7 H7 120.00 . . . no
C8 C7 H7 119.00 . . . no
C7 C8 H8 120.00 . . . no
C9 C8 H8 120.00 . . . no
C4 C9 H9 120.00 . . . no
C8 C9 H9 119.00 . . . no
O3 C10 H10A 110.00 . . . no
O3 C10 H10B 110.00 . . . no
C13 C10 H10A 110.00 . . . no
C13 C10 H10B 110.00 . . . no
H10A C10 H10B 108.00 . . . no
C12 C11 H11 119.00 . . . no
C20 C11 H11 119.00 . . . no
C11 C12 H12 119.00 . . . no
C13 C12 H12 120.00 . . . no
C13 C14 H14 118.00 . . . no
C15 C14 H14 118.00 . . . no
C15 C16 H16A 109.00 . . . no
C15 C16 H16B 109.00 . . . no
C17 C16 H16A 109.00 . . . no
C17 C16 H16B 109.00 . . . no
H16A C16 H16B 108.00 . . . no
C16 C17 H17A 109.00 . . . no
C16 C17 H17B 109.00 . . . no
C18 C17 H17A 109.00 . . . no
C18 C17 H17B 109.00 . . . no
H17A C17 H17B 108.00 . . . no
C17 C18 H18 108.00 . . . no
C19 C18 H18 108.00 . . . no
C24 C18 H18 109.00 . . . no
C18 C19 H19 106.00 . . . no
C20 C19 H19 106.00 . . . no
C21 C19 H19 106.00 . . . no
C19 C21 H21A 109.00 . . . no
C19 C21 H21B 109.00 . . . no
C22 C21 H21A 109.00 . . . no
C22 C21 H21B 109.00 . . . no
H21A C21 H21B 108.00 . . . no
C21 C22 H22A 109.00 . . . no
C21 C22 H22B 109.00 . . . no
C23 C22 H22A 109.00 . . . no
C23 C22 H22B 109.00 . . . no
H22A C22 H22B 108.00 . . . no
C18 C24 H24 106.00 . . . no
C23 C24 H24 106.00 . . . no
C25 C24 H24 106.00 . . . no
C24 C25 H25A 110.00 . . . no
C24 C25 H25B 111.00 . . . no
C26 C25 H25A 111.00 . . . no
C26 C25 H25B 111.00 . . . no
H25A C25 H25B 109.00 . . . no
C25 C26 H26A 110.00 . . . no
C25 C26 H26B 110.00 . . . no
C27 C26 H26A 111.00 . . . no
C27 C26 H26B 111.00 . . . no
H26A C26 H26B 109.00 . . . no
C23 C27 H27A 111.00 . . . no
C23 C27 H27B 111.00 . . . no
C26 C27 H27A 111.00 . . . no
C26 C27 H27B 111.00 . . . no
H27A C27 H27B 109.00 . . . no
C23 C28 H28A 110.00 . . . no
C23 C28 H28B 109.00 . . . no
C23 C28 H28C 109.00 . . . no
H28A C28 H28B 109.00 . . . no
H28A C28 H28C 109.00 . . . no
H28B C28 H28C 110.00 . . . no
O4 C29 H29A 109.00 . . . no
O4 C29 H29B 110.00 . . . no
C30 C29 H29A 110.00 . . . no
C30 C29 H29B 109.00 . . . no
H29A C29 H29B 108.00 . . . no
C29 C30 H30A 109.00 . . . no
C29 C30 H30B 110.00 . . . no
C29 C30 H30C 109.00 . . . no
H30A C30 H30B 109.00 . . . no
H30A C30 H30C 110.00 . . . no
H30B C30 H30C 109.00 . . . no

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 S1 C2 C1 74.5(4) . . . . no
O2 P1 O3 C10 61.2(5) . . . . no
O4 P1 O3 C10 -63.5(5) . . . . no
C1 P1 O3 C10 -175.6(4) . . . . no
O2 P1 O4 C29 21.8(5) . . . . no
O3 P1 O4 C29 146.9(4) . . . . no
C1 P1 O4 C29 -103.8(4) . . . . no
O2 P1 C1 O1 -61.4(3) . . . . no
O2 P1 C1 C2 56.8(4) . . . . no
O2 P1 C1 C4 -177.3(3) . . . . no
O3 P1 C1 O1 174.0(3) . . . . no
O3 P1 C1 C2 -67.8(3) . . . . no
O3 P1 C1 C4 58.1(4) . . . . no
O4 P1 C1 O1 65.0(3) . . . . no
O4 P1 C1 C2 -176.8(3) . . . . no
O4 P1 C1 C4 -50.9(4) . . . . no
P1 O3 C10 C13 -171.8(4) . . . . no
P1 O4 C29 C30 -98.5(6) . . . . no
P1 C1 C2 S1 175.6(2) . . . . no
O1 C1 C2 S1 -71.1(4) . . . . no
C4 C1 C2 S1 51.4(5) . . . . no
P1 C1 C4 C5 -79.2(5) . . . . no
P1 C1 C4 C9 100.9(4) . . . . no
O1 C1 C4 C5 168.3(4) . . . . no
O1 C1 C4 C9 -11.6(6) . . . . no
C2 C1 C4 C5 44.4(6) . . . . no
C2 C1 C4 C9 -135.5(4) . . . . no
C1 C4 C5 C6 -179.6(4) . . . . no
C9 C4 C5 C6 0.3(7) . . . . no
C1 C4 C9 C8 179.7(5) . . . . no
C5 C4 C9 C8 -0.2(7) . . . . no
C4 C5 C6 C7 0.2(8) . . . . no
C5 C6 C7 C8 -0.9(10) . . . . no
C6 C7 C8 C9 1.0(10) . . . . no
C7 C8 C9 C4 -0.5(9) . . . . no
O3 C10 C13 C12 -160.9(5) . . . . no
O3 C10 C13 C14 21.9(7) . . . . no
C20 C11 C12 C13 1.4(7) . . . . no
C12 C11 C20 C15 -3.0(7) . . . . no
C12 C11 C20 C19 176.1(4) . . . . no
C11 C12 C13 C10 -177.7(5) . . . . no
C11 C12 C13 C14 -0.3(7) . . . . no
C10 C13 C14 C15 178.2(5) . . . . no
C12 C13 C14 C15 1.0(8) . . . . no
C13 C14 C15 C16 177.5(5) . . . . no
C13 C14 C15 C20 -2.6(8) . . . . no
C14 C15 C16 C17 167.3(5) . . . . no
C20 C15 C16 C17 -12.6(6) . . . . no
C14 C15 C20 C11 3.5(7) . . . . no
C14 C15 C20 C19 -175.5(4) . . . . no
C16 C15 C20 C11 -176.7(4) . . . . no
C16 C15 C20 C19 4.3(7) . . . . no
C15 C16 C17 C18 41.5(5) . . . . no
C16 C17 C18 C19 -61.4(5) . . . . no
C16 C17 C18 C24 176.6(3) . . . . no
C17 C18 C19 C20 51.6(5) . . . . no
C17 C18 C19 C21 -177.6(4) . . . . no
C24 C18 C19 C20 176.7(4) . . . . no
C24 C18 C19 C21 -52.5(5) . . . . no
C17 C18 C24 C23 179.8(3) . . . . no
C17 C18 C24 C25 -55.8(6) . . . . no
C19 C18 C24 C23 57.7(5) . . . . no
C19 C18 C24 C25 -177.8(4) . . . . no
C18 C19 C20 C11 156.7(4) . . . . no
C18 C19 C20 C15 -24.4(6) . . . . no
C21 C19 C20 C11 27.2(6) . . . . no
C21 C19 C20 C15 -153.8(4) . . . . no
C18 C19 C21 C22 51.8(5) . . . . no
C20 C19 C21 C22 -178.5(4) . . . . no
C19 C21 C22 C23 -53.0(5) . . . . no
C21 C22 C23 C24 53.9(6) . . . . no
C21 C22 C23 C27 166.6(4) . . . . no
C21 C22 C23 C28 -69.5(5) . . . . no
C22 C23 C24 C18 -58.8(5) . . . . no
C22 C23 C24 C25 167.8(5) . . . . no
C27 C23 C24 C18 178.4(4) . . . . no
C27 C23 C24 C25 44.9(5) . . . . no
C28 C23 C24 C18 63.3(5) . . . . no
C28 C23 C24 C25 -70.2(6) . . . . no
C22 C23 C27 C26 -158.8(5) . . . . no
C24 C23 C27 C26 -41.7(5) . . . . no
C28 C23 C27 C26 76.3(6) . . . . no
C18 C24 C25 C26 -160.9(5) . . . . no
C23 C24 C25 C26 -31.2(6) . . . . no
C24 C25 C26 C27 5.0(7) . . . . no
C25 C26 C27 C23 22.9(7) . . . . no


# H-bond

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
_geom_hbond_publ_flag
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
O1 H1 O2 0.8800 1.8600 2.727(4) 169.00 2_555 yes





#===============================================================================

# 7. Validation Reply Form

_vrf_THETM01_compound23          
;
PROBLEM:
Alert level B
THETM01_ALERT_3_B  The value of sine(theta_max)/wavelength is less than 0.575
            Calculated sin(theta_max)/wavelength =    0.5723
RESPONSE: 
No CCD area detector diffractometer was available at the time of the
corresponding experiments. Therefore, a PHILIPS PW1100 X-ray four circle
diffractometer with a point detector in sequential measurement of each
single reflection had to be used without crystal cooling. Because of
a significant decline in intensities at higher Bragg angles, data collection
had to be limited to theta(max) = 24deg (MoKalfa radiation).
Making use of the known stable absolute configuration of the 
1,3,5(10)-estratrien-3-ol applied in the construction of the 
title compound (compound23), its absolute structure could be 
reliably determined despite the low theta cutoff.
;

_vrf_REFNR01_compound23          
;
PROBLEM:
Alert level C
REFNR01_ALERT_3_C  Ratio of reflections to parameters is < 8 for a
            non-centrosymmetric structure, where ZMAX < 18
            sine(theta)/lambda                0.5723
            Proportion of unique data used    0.9988
            Ratio reflections to parameters   7.4731
RESPONSE: 
Due to the prolonged measurement time with the X-ray instrument given above,
only a quarter of an Ewald sphere could be measured.
;

# end Validation Reply Form

#===END
#=============================end of CIF======================================= 




_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexanes, isopropanol'
