 
data_1 
  
_audit_creation_method            'SHELXL-2014/7' 
_shelx_SHELXL_version_number      '2014/7' 
_chemical_name_systematic         ? 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C24 H27 O2 P S' 
_chemical_formula_weight          410.48 
  
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                    14.4632(6) 
_cell_length_b                    10.7632(5) 
_cell_length_c                    14.5754(6) 
_cell_angle_alpha                 90 
_cell_angle_beta                  105.3574(13) 
_cell_angle_gamma                 90 
_cell_volume                      2187.94(16) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     296(2) 
_cell_measurement_reflns_used     3503 
_cell_measurement_theta_min       2.38 
_cell_measurement_theta_max       26.34 
  
_exptl_crystal_description        plate 
_exptl_crystal_colour             colourless 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ? 
_exptl_crystal_density_diffrn     1.246 
_exptl_crystal_F_000              872 
_exptl_transmission_factor_min    ? 
_exptl_transmission_factor_max    ? 
_exptl_crystal_size_max           0.280 
_exptl_crystal_size_mid           0.240 
_exptl_crystal_size_min           0.110 
_exptl_absorpt_coefficient_mu     0.238 
_shelx_estimated_absorpt_T_min    0.936 
_shelx_estimated_absorpt_T_max    0.974 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.6652 
_exptl_absorpt_correction_T_max   0.7454 
_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             12846 
_diffrn_reflns_av_unetI/netI      0.0579 
_diffrn_reflns_av_R_equivalents   0.0546 
_diffrn_reflns_limit_h_min        -17 
_diffrn_reflns_limit_h_max        14 
_diffrn_reflns_limit_k_min        -12 
_diffrn_reflns_limit_k_max        12 
_diffrn_reflns_limit_l_min        -17 
_diffrn_reflns_limit_l_max        16 
_diffrn_reflns_theta_min          2.383 
_diffrn_reflns_theta_max          25.000 
_diffrn_reflns_theta_full         25.000 
_diffrn_measured_fraction_theta_max   0.999 
_diffrn_measured_fraction_theta_full  0.999 
_diffrn_reflns_Laue_measured_fraction_max    0.999 
_diffrn_reflns_Laue_measured_fraction_full   0.999 
_diffrn_reflns_point_group_measured_fraction_max   0.999 
_diffrn_reflns_point_group_measured_fraction_full  0.999 
_reflns_number_total              3856 
_reflns_number_gt                 2419 
_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-2014/7 (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)+(0.0326P)²+0.6493P] 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          3856 
_refine_ls_number_parameters      254 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0901 
_refine_ls_R_factor_gt            0.0448 
_refine_ls_wR_factor_ref          0.1002 
_refine_ls_wR_factor_gt           0.0840 
_refine_ls_goodness_of_fit_ref    1.009 
_refine_ls_restrained_S_all       1.009 
_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 1.36013(18) 0.3829(3) 0.2721(2) 0.0486(7) Uani 1 1 d . . . . . 
C2 C 1.4378(2) 0.4065(3) 0.3483(2) 0.0704(9) Uani 1 1 d . . . . . 
H2 H 1.4409 0.4800 0.3825 0.085 Uiso 1 1 calc R U . . . 
C3 C 1.5115(2) 0.3203(5) 0.3737(3) 0.0911(13) Uani 1 1 d . . . . . 
H3 H 1.5638 0.3362 0.4253 0.109 Uiso 1 1 calc R U . . . 
C4 C 1.5080(3) 0.2125(4) 0.3239(3) 0.0923(13) Uani 1 1 d . . . . . 
H4 H 1.5578 0.1553 0.3409 0.111 Uiso 1 1 calc R U . . . 
C5 C 1.4315(3) 0.1894(3) 0.2495(3) 0.0889(12) Uani 1 1 d . . . . . 
H5 H 1.4286 0.1153 0.2160 0.107 Uiso 1 1 calc R U . . . 
C6 C 1.3578(2) 0.2740(3) 0.2227(2) 0.0701(9) Uani 1 1 d . . . . . 
H6 H 1.3062 0.2572 0.1707 0.084 Uiso 1 1 calc R U . . . 
C7 C 1.16041(17) 0.4094(2) 0.2029(2) 0.0467(7) Uani 1 1 d . . . . . 
H7A H 1.1465 0.3904 0.1355 0.056 Uiso 1 1 calc R U . . . 
H7B H 1.1674 0.3317 0.2377 0.056 Uiso 1 1 calc R U . . . 
C8 C 1.07947(17) 0.4839(2) 0.22234(19) 0.0409(6) Uani 1 1 d . . . . . 
H8 H 1.0953 0.5035 0.2904 0.049 Uiso 1 1 calc R U . . . 
C9 C 0.88924(17) 0.4878(2) 0.24688(17) 0.0401(6) Uani 1 1 d . . . . . 
H9A H 0.9055 0.5752 0.2469 0.048 Uiso 1 1 calc R U . . . 
H9B H 0.8227 0.4782 0.2113 0.048 Uiso 1 1 calc R U . . . 
C10 C 0.9016(3) 0.4443(3) 0.3484(2) 0.0758(10) Uani 1 1 d . . . . . 
H10A H 0.8762 0.3607 0.3468 0.091 Uiso 1 1 calc R U . . . 
H10B H 0.9697 0.4402 0.3797 0.091 Uiso 1 1 calc R U . . . 
C11 C 0.8542(2) 0.5240(3) 0.40753(19) 0.0503(7) Uani 1 1 d . . . . . 
C12 C 0.8989(2) 0.6275(3) 0.4543(2) 0.0618(8) Uani 1 1 d . . . . . 
H12 H 0.9576 0.6523 0.4455 0.074 Uiso 1 1 calc R U . . . 
C13 C 0.8582(3) 0.6952(3) 0.5139(2) 0.0746(10) Uani 1 1 d . . . . . 
H13 H 0.8903 0.7637 0.5462 0.090 Uiso 1 1 calc R U . . . 
C14 C 0.7713(3) 0.6619(4) 0.5256(2) 0.0799(11) Uani 1 1 d . . . . . 
H14 H 0.7435 0.7078 0.5653 0.096 Uiso 1 1 calc R U . . . 
C15 C 0.7255(3) 0.5610(4) 0.4789(3) 0.0798(11) Uani 1 1 d . . . . . 
H15 H 0.6661 0.5378 0.4866 0.096 Uiso 1 1 calc R U . . . 
C16 C 0.7663(2) 0.4933(3) 0.4204(2) 0.0657(9) Uani 1 1 d . . . . . 
H16 H 0.7337 0.4248 0.3886 0.079 Uiso 1 1 calc R U . . . 
C17 C 0.92111(18) 0.4160(2) 0.06260(18) 0.0450(7) Uani 1 1 d . . . . . 
H17A H 0.8999 0.5010 0.0483 0.054 Uiso 1 1 calc R U . . . 
H17B H 0.9737 0.4012 0.0343 0.054 Uiso 1 1 calc R U . . . 
C18 C 0.83822(19) 0.3282(3) 0.01606(19) 0.0507(7) Uani 1 1 d . . . . . 
H18A H 0.8232 0.3376 -0.0525 0.061 Uiso 1 1 calc R U . . . 
H18B H 0.8585 0.2431 0.0313 0.061 Uiso 1 1 calc R U . . . 
C19 C 0.74948(19) 0.3528(3) 0.04827(19) 0.0452(7) Uani 1 1 d . . . . . 
C20 C 0.6991(2) 0.4630(3) 0.0249(2) 0.0603(8) Uani 1 1 d . . . . . 
H20 H 0.7173 0.5193 -0.0155 0.072 Uiso 1 1 calc R U . . . 
C21 C 0.6225(2) 0.4899(3) 0.0609(3) 0.0763(10) Uani 1 1 d . . . . . 
H21 H 0.5900 0.5648 0.0456 0.092 Uiso 1 1 calc R U . . . 
C22 C 0.5938(2) 0.4066(4) 0.1193(3) 0.0818(11) Uani 1 1 d . . . . . 
H22 H 0.5418 0.4248 0.1433 0.098 Uiso 1 1 calc R U . . . 
C23 C 0.6420(2) 0.2971(3) 0.1419(2) 0.0715(10) Uani 1 1 d . . . . . 
H23 H 0.6227 0.2404 0.1813 0.086 Uiso 1 1 calc R U . . . 
C24 C 0.7189(2) 0.2703(3) 0.1067(2) 0.0573(8) Uani 1 1 d . . . . . 
H24 H 0.7510 0.1952 0.1226 0.069 Uiso 1 1 calc R U . . . 
O1 O 1.06832(14) 0.59706(15) 0.17016(13) 0.0502(5) Uani 1 1 d . . . . . 
H1 H 1.0550 0.6531 0.2025 0.075 Uiso 1 1 calc R U . . . 
O2 O 0.97674(13) 0.26623(15) 0.21947(13) 0.0491(5) Uani 1 1 d . . . . . 
P1 P 0.96492(5) 0.39952(6) 0.18971(5) 0.03774(19) Uani 1 1 d . . . . . 
S1 S 1.27029(5) 0.49816(7) 0.23943(6) 0.0580(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 C6 1.371(4) . ? 
C1 C2 1.378(4) . ? 
C1 S1 1.768(3) . ? 
C2 C3 1.387(5) . ? 
C2 H2 0.9300 . ? 
C3 C4 1.363(5) . ? 
C3 H3 0.9300 . ? 
C4 C5 1.351(5) . ? 
C4 H4 0.9300 . ? 
C5 C6 1.378(4) . ? 
C5 H5 0.9300 . ? 
C6 H6 0.9300 . ? 
C7 C8 1.507(3) . ? 
C7 S1 1.810(2) . ? 
C7 H7A 0.9700 . ? 
C7 H7B 0.9700 . ? 
C8 O1 1.422(3) . ? 
C8 P1 1.838(3) . ? 
C8 H8 0.9800 . ? 
C9 C10 1.517(4) . ? 
C9 P1 1.810(2) . ? 
C9 H9A 0.9700 . ? 
C9 H9B 0.9700 . ? 
C10 C11 1.503(4) . ? 
C10 H10A 0.9700 . ? 
C10 H10B 0.9700 . ? 
C11 C16 1.374(4) . ? 
C11 C12 1.375(4) . ? 
C12 C13 1.380(4) . ? 
C12 H12 0.9300 . ? 
C13 C14 1.361(5) . ? 
C13 H13 0.9300 . ? 
C14 C15 1.357(5) . ? 
C14 H14 0.9300 . ? 
C15 C16 1.368(4) . ? 
C15 H15 0.9300 . ? 
C16 H16 0.9300 . ? 
C17 C18 1.536(3) . ? 
C17 P1 1.801(3) . ? 
C17 H17A 0.9700 . ? 
C17 H17B 0.9700 . ? 
C18 C19 1.502(3) . ? 
C18 H18A 0.9700 . ? 
C18 H18B 0.9700 . ? 
C19 C24 1.382(4) . ? 
C19 C20 1.386(4) . ? 
C20 C21 1.377(4) . ? 
C20 H20 0.9300 . ? 
C21 C22 1.374(5) . ? 
C21 H21 0.9300 . ? 
C22 C23 1.365(4) . ? 
C22 H22 0.9300 . ? 
C23 C24 1.373(4) . ? 
C23 H23 0.9300 . ? 
C24 H24 0.9300 . ? 
O1 H1 0.8200 . ? 
O2 P1 1.4954(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 
C6 C1 C2 118.8(3) . . ? 
C6 C1 S1 123.0(2) . . ? 
C2 C1 S1 118.1(2) . . ? 
C1 C2 C3 119.8(3) . . ? 
C1 C2 H2 120.1 . . ? 
C3 C2 H2 120.1 . . ? 
C4 C3 C2 120.6(4) . . ? 
C4 C3 H3 119.7 . . ? 
C2 C3 H3 119.7 . . ? 
C5 C4 C3 119.5(4) . . ? 
C5 C4 H4 120.3 . . ? 
C3 C4 H4 120.3 . . ? 
C4 C5 C6 120.9(4) . . ? 
C4 C5 H5 119.6 . . ? 
C6 C5 H5 119.5 . . ? 
C1 C6 C5 120.4(3) . . ? 
C1 C6 H6 119.8 . . ? 
C5 C6 H6 119.8 . . ? 
C8 C7 S1 109.21(18) . . ? 
C8 C7 H7A 109.8 . . ? 
S1 C7 H7A 109.8 . . ? 
C8 C7 H7B 109.8 . . ? 
S1 C7 H7B 109.8 . . ? 
H7A C7 H7B 108.3 . . ? 
O1 C8 C7 109.8(2) . . ? 
O1 C8 P1 108.54(17) . . ? 
C7 C8 P1 112.34(17) . . ? 
O1 C8 H8 108.7 . . ? 
C7 C8 H8 108.7 . . ? 
P1 C8 H8 108.7 . . ? 
C10 C9 P1 110.96(18) . . ? 
C10 C9 H9A 109.4 . . ? 
P1 C9 H9A 109.4 . . ? 
C10 C9 H9B 109.4 . . ? 
P1 C9 H9B 109.4 . . ? 
H9A C9 H9B 108.0 . . ? 
C11 C10 C9 115.4(2) . . ? 
C11 C10 H10A 108.4 . . ? 
C9 C10 H10A 108.4 . . ? 
C11 C10 H10B 108.4 . . ? 
C9 C10 H10B 108.4 . . ? 
H10A C10 H10B 107.5 . . ? 
C16 C11 C12 117.2(3) . . ? 
C16 C11 C10 121.4(3) . . ? 
C12 C11 C10 121.4(3) . . ? 
C11 C12 C13 121.2(3) . . ? 
C11 C12 H12 119.4 . . ? 
C13 C12 H12 119.4 . . ? 
C14 C13 C12 120.1(3) . . ? 
C14 C13 H13 120.0 . . ? 
C12 C13 H13 120.0 . . ? 
C15 C14 C13 119.5(3) . . ? 
C15 C14 H14 120.3 . . ? 
C13 C14 H14 120.3 . . ? 
C14 C15 C16 120.3(3) . . ? 
C14 C15 H15 119.8 . . ? 
C16 C15 H15 119.8 . . ? 
C15 C16 C11 121.6(3) . . ? 
C15 C16 H16 119.2 . . ? 
C11 C16 H16 119.2 . . ? 
C18 C17 P1 114.50(18) . . ? 
C18 C17 H17A 108.6 . . ? 
P1 C17 H17A 108.6 . . ? 
C18 C17 H17B 108.6 . . ? 
P1 C17 H17B 108.6 . . ? 
H17A C17 H17B 107.6 . . ? 
C19 C18 C17 112.7(2) . . ? 
C19 C18 H18A 109.1 . . ? 
C17 C18 H18A 109.1 . . ? 
C19 C18 H18B 109.1 . . ? 
C17 C18 H18B 109.1 . . ? 
H18A C18 H18B 107.8 . . ? 
C24 C19 C20 117.9(3) . . ? 
C24 C19 C18 121.3(3) . . ? 
C20 C19 C18 120.7(3) . . ? 
C21 C20 C19 120.7(3) . . ? 
C21 C20 H20 119.7 . . ? 
C19 C20 H20 119.7 . . ? 
C22 C21 C20 120.3(3) . . ? 
C22 C21 H21 119.9 . . ? 
C20 C21 H21 119.9 . . ? 
C23 C22 C21 119.6(3) . . ? 
C23 C22 H22 120.2 . . ? 
C21 C22 H22 120.2 . . ? 
C22 C23 C24 120.2(3) . . ? 
C22 C23 H23 119.9 . . ? 
C24 C23 H23 119.9 . . ? 
C23 C24 C19 121.2(3) . . ? 
C23 C24 H24 119.4 . . ? 
C19 C24 H24 119.4 . . ? 
C8 O1 H1 109.5 . . ? 
O2 P1 C17 112.01(11) . . ? 
O2 P1 C9 113.98(11) . . ? 
C17 P1 C9 109.33(12) . . ? 
O2 P1 C8 111.90(11) . . ? 
C17 P1 C8 105.37(12) . . ? 
C9 P1 C8 103.59(12) . . ? 
C1 S1 C7 103.54(13) . . ? 
  
_refine_diff_density_max    0.204 
_refine_diff_density_min   -0.192 
_refine_diff_density_rms    0.040 
  
  
  
