# Electronic Supplementary Material (ESI) for RSC Advances
# This journal is © The Royal Society of Chemistry 2012


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#  This CIF contains data from an original supplementary publication 
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#  experimental, refinement, atomic coordinates, 
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted. 
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data_071123a
_database_code_depnum_ccdc_archive 'CCDC 675752'
#TrackingRef '- 071123A-new revision.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H21 Br N O2 P S'
_chemical_formula_weight         486.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   17.142(4)
_cell_length_b                   14.596(3)
_cell_length_c                   18.909(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.326(4)
_cell_angle_gamma                90.00
_cell_volume                     4407.1(16)
_cell_formula_units_Z            8
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    8456
_cell_measurement_theta_min      3.54
_cell_measurement_theta_max      27.61

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1984
_exptl_absorpt_coefficient_mu    2.052
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.5780
_exptl_absorpt_correction_T_max  0.6387
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       '\f scans, and \w scans with \k offsets'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            12410
_diffrn_reflns_av_R_equivalents  0.0556
_diffrn_reflns_av_sigmaI/netI    0.0655
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.89
_diffrn_reflns_theta_max         26.43
_reflns_number_total             4522
_reflns_number_gt                2638
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0460P)^2^+7.4162P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4522
_refine_ls_number_parameters     267
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1036
_refine_ls_R_factor_gt           0.0472
_refine_ls_wR_factor_ref         0.1251
_refine_ls_wR_factor_gt          0.1018
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 1.02462(3) 0.96087(4) 0.14487(4) 0.0820(2) Uani 1 1 d . . .
P1 P 0.68792(6) 0.83156(6) 0.16870(6) 0.0316(2) Uani 1 1 d . . .
S1 S 0.73235(6) 0.83098(7) 0.27942(6) 0.0441(3) Uani 1 1 d . . .
O1 O 0.92357(16) 0.56792(19) 0.15041(16) 0.0489(7) Uani 1 1 d . . .
O2 O 0.75887(18) 0.6462(2) 0.01776(16) 0.0520(7) Uani 1 1 d . . .
N1 N 0.74592(18) 0.7746(2) 0.13086(17) 0.0341(7) Uani 1 1 d D . .
C1 C 0.8101(2) 0.7073(2) 0.1693(2) 0.0319(8) Uani 1 1 d . . .
H1 H 0.8211 0.7123 0.2238 0.038 Uiso 1 1 calc R . .
C2 C 0.8918(2) 0.7291(3) 0.1582(2) 0.0327(8) Uani 1 1 d . . .
C3 C 0.9173(2) 0.8183(3) 0.1565(2) 0.0426(10) Uani 1 1 d . . .
H3 H 0.8846 0.8662 0.1628 0.051 Uiso 1 1 calc R . .
C4 C 0.9913(3) 0.8369(3) 0.1457(2) 0.0496(11) Uani 1 1 d . . .
C5 C 1.0398(2) 0.7667(4) 0.1346(2) 0.0533(12) Uani 1 1 d . . .
H5 H 1.0886 0.7798 0.1259 0.064 Uiso 1 1 calc R . .
C6 C 1.0155(2) 0.6783(3) 0.1364(2) 0.0483(11) Uani 1 1 d . . .
H6 H 1.0479 0.6307 0.1292 0.058 Uiso 1 1 calc R . .
C7 C 0.9426(2) 0.6592(3) 0.1491(2) 0.0383(9) Uani 1 1 d . . .
C8 C 0.8610(2) 0.5475(3) 0.1816(2) 0.0457(10) Uani 1 1 d . . .
H8A H 0.8839 0.5573 0.2360 0.055 Uiso 1 1 calc R . .
H8B H 0.8450 0.4836 0.1724 0.055 Uiso 1 1 calc R . .
C9 C 0.7839(2) 0.6079(2) 0.1460(2) 0.0359(9) Uani 1 1 d . . .
H9 H 0.7420 0.5901 0.1675 0.043 Uiso 1 1 calc R . .
C10 C 0.7468(2) 0.5926(3) 0.0610(2) 0.0383(9) Uani 1 1 d . . .
C11 C 0.6955(3) 0.5076(3) 0.0341(3) 0.0702(14) Uani 1 1 d . . .
H11A H 0.6849 0.4985 -0.0189 0.105 Uiso 1 1 calc R . .
H11B H 0.6433 0.5140 0.0415 0.105 Uiso 1 1 calc R . .
H11C H 0.7255 0.4558 0.0625 0.105 Uiso 1 1 calc R . .
C12 C 0.6810(2) 0.9452(2) 0.1280(2) 0.0366(9) Uani 1 1 d . . .
C13 C 0.7390(3) 1.0107(3) 0.1674(3) 0.0504(11) Uani 1 1 d . . .
H13 H 0.7783 0.9971 0.2152 0.061 Uiso 1 1 calc R . .
C14 C 0.7384(3) 1.0958(3) 0.1358(3) 0.0660(14) Uani 1 1 d . . .
H14 H 0.7775 1.1396 0.1623 0.079 Uiso 1 1 calc R . .
C15 C 0.6810(4) 1.1161(3) 0.0660(4) 0.0700(15) Uani 1 1 d . . .
H15 H 0.6807 1.1741 0.0455 0.084 Uiso 1 1 calc R . .
C16 C 0.6237(3) 1.0523(3) 0.0255(3) 0.0650(14) Uani 1 1 d . . .
H16 H 0.5852 1.0666 -0.0224 0.078 Uiso 1 1 calc R . .
C17 C 0.6232(3) 0.9663(3) 0.0564(2) 0.0481(11) Uani 1 1 d . . .
H17 H 0.5843 0.9227 0.0292 0.058 Uiso 1 1 calc R . .
C18 C 0.5830(2) 0.7845(2) 0.1312(2) 0.0344(9) Uani 1 1 d . . .
C19 C 0.5241(2) 0.8123(3) 0.1610(3) 0.0566(12) Uani 1 1 d . . .
H19 H 0.5377 0.8578 0.1980 0.068 Uiso 1 1 calc R . .
C20 C 0.4455(3) 0.7733(4) 0.1363(3) 0.0717(15) Uani 1 1 d . . .
H20 H 0.4064 0.7926 0.1566 0.086 Uiso 1 1 calc R . .
C21 C 0.4247(3) 0.7061(3) 0.0819(3) 0.0615(13) Uani 1 1 d . . .
H21 H 0.3722 0.6786 0.0663 0.074 Uiso 1 1 calc R . .
C22 C 0.4810(3) 0.6801(3) 0.0511(3) 0.0546(11) Uani 1 1 d . . .
H22 H 0.4664 0.6355 0.0135 0.065 Uiso 1 1 calc R . .
C23 C 0.5601(2) 0.7189(3) 0.0747(2) 0.0464(10) Uani 1 1 d . . .
H23 H 0.5979 0.7006 0.0524 0.056 Uiso 1 1 calc R . .
H1A H 0.742(2) 0.796(2) 0.0858(10) 0.029(10) Uiso 1 1 d D . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0695(4) 0.0677(4) 0.1057(5) 0.0135(3) 0.0283(3) -0.0272(3)
P1 0.0315(5) 0.0335(5) 0.0345(6) -0.0017(4) 0.0178(4) 0.0023(4)
S1 0.0450(6) 0.0574(7) 0.0334(6) -0.0027(5) 0.0187(5) 0.0078(5)
O1 0.0501(16) 0.0392(16) 0.065(2) 0.0001(14) 0.0293(15) 0.0103(13)
O2 0.0711(19) 0.0516(18) 0.0385(17) 0.0043(14) 0.0262(15) -0.0007(15)
N1 0.0398(17) 0.0390(18) 0.0293(18) 0.0049(15) 0.0196(15) 0.0095(14)
C1 0.0354(19) 0.035(2) 0.030(2) 0.0022(16) 0.0186(17) 0.0054(16)
C2 0.0310(19) 0.038(2) 0.031(2) 0.0006(17) 0.0133(16) -0.0002(17)
C3 0.041(2) 0.043(2) 0.045(2) 0.0040(19) 0.0164(19) 0.0010(18)
C4 0.041(2) 0.054(3) 0.048(3) 0.009(2) 0.011(2) -0.016(2)
C5 0.036(2) 0.082(4) 0.046(3) 0.012(2) 0.021(2) 0.000(2)
C6 0.039(2) 0.065(3) 0.044(3) 0.007(2) 0.018(2) 0.013(2)
C7 0.036(2) 0.047(3) 0.033(2) 0.0017(18) 0.0131(17) 0.0054(18)
C8 0.051(2) 0.037(2) 0.050(3) 0.006(2) 0.018(2) 0.0018(19)
C9 0.042(2) 0.033(2) 0.040(2) 0.0015(17) 0.0236(19) -0.0024(17)
C10 0.037(2) 0.038(2) 0.044(2) -0.007(2) 0.0191(19) 0.0012(17)
C11 0.072(3) 0.066(3) 0.067(3) -0.022(3) 0.019(3) -0.019(3)
C12 0.039(2) 0.034(2) 0.046(2) -0.0034(19) 0.0258(19) 0.0028(17)
C13 0.060(3) 0.043(3) 0.055(3) -0.005(2) 0.028(2) -0.006(2)
C14 0.085(4) 0.035(3) 0.097(4) -0.012(3) 0.056(3) -0.012(2)
C15 0.087(4) 0.039(3) 0.112(5) 0.017(3) 0.070(4) 0.014(3)
C16 0.069(3) 0.061(3) 0.075(4) 0.030(3) 0.037(3) 0.024(3)
C17 0.045(2) 0.053(3) 0.052(3) 0.010(2) 0.024(2) 0.008(2)
C18 0.035(2) 0.034(2) 0.040(2) 0.0010(18) 0.0201(18) 0.0008(16)
C19 0.045(2) 0.074(3) 0.058(3) -0.018(3) 0.027(2) -0.007(2)
C20 0.044(3) 0.101(4) 0.084(4) -0.013(3) 0.041(3) -0.016(3)
C21 0.044(3) 0.076(3) 0.064(3) -0.001(3) 0.020(2) -0.022(2)
C22 0.056(3) 0.048(3) 0.055(3) -0.007(2) 0.015(2) -0.013(2)
C23 0.045(2) 0.044(2) 0.055(3) -0.009(2) 0.024(2) -0.0027(19)

_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
Br1 C4 1.899(4) . ?
P1 N1 1.646(3) . ?
P1 C18 1.811(4) . ?
P1 C12 1.814(4) . ?
P1 S1 1.9501(15) . ?
O1 C7 1.373(5) . ?
O1 C8 1.430(5) . ?
O2 C10 1.202(5) . ?
N1 C1 1.457(4) . ?
N1 H1A 0.888(10) . ?
C1 C2 1.523(5) . ?
C1 C9 1.535(5) . ?
C1 H1 0.9800 . ?
C2 C3 1.377(5) . ?
C2 C7 1.392(5) . ?
C3 C4 1.384(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.383(6) . ?
C5 C6 1.360(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.384(5) . ?
C6 H6 0.9300 . ?
C8 C9 1.525(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.515(5) . ?
C9 H9 0.9800 . ?
C10 C11 1.499(6) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.386(6) . ?
C12 C17 1.390(5) . ?
C13 C14 1.377(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.363(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.367(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.386(6) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C23 1.381(5) . ?
C18 C19 1.384(5) . ?
C19 C20 1.380(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.370(6) . ?
C20 H20 0.9300 . ?
C21 C22 1.351(6) . ?
C21 H21 0.9300 . ?
C22 C23 1.385(5) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?

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
N1 P1 C18 107.96(17) . . ?
N1 P1 C12 103.55(16) . . ?
C18 P1 C12 106.12(17) . . ?
N1 P1 S1 113.74(12) . . ?
C18 P1 S1 111.32(13) . . ?
C12 P1 S1 113.55(14) . . ?
C7 O1 C8 115.3(3) . . ?
C1 N1 P1 126.2(2) . . ?
C1 N1 H1A 120(2) . . ?
P1 N1 H1A 113(2) . . ?
N1 C1 C2 110.8(3) . . ?
N1 C1 C9 113.9(3) . . ?
C2 C1 C9 110.2(3) . . ?
N1 C1 H1 107.2 . . ?
C2 C1 H1 107.2 . . ?
C9 C1 H1 107.2 . . ?
C3 C2 C7 118.2(3) . . ?
C3 C2 C1 121.1(3) . . ?
C7 C2 C1 120.7(3) . . ?
C2 C3 C4 120.4(4) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 120.7(4) . . ?
C5 C4 Br1 120.4(3) . . ?
C3 C4 Br1 118.9(3) . . ?
C6 C5 C4 119.5(4) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C5 C6 C7 120.1(4) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
O1 C7 C6 115.7(4) . . ?
O1 C7 C2 123.1(3) . . ?
C6 C7 C2 121.2(4) . . ?
O1 C8 C9 110.9(3) . . ?
O1 C8 H8A 109.5 . . ?
C9 C8 H8A 109.5 . . ?
O1 C8 H8B 109.5 . . ?
C9 C8 H8B 109.5 . . ?
H8A C8 H8B 108.0 . . ?
C10 C9 C8 110.2(3) . . ?
C10 C9 C1 114.2(3) . . ?
C8 C9 C1 107.7(3) . . ?
C10 C9 H9 108.2 . . ?
C8 C9 H9 108.2 . . ?
C1 C9 H9 108.2 . . ?
O2 C10 C11 122.2(4) . . ?
O2 C10 C9 121.1(3) . . ?
C11 C10 C9 116.7(4) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C17 119.3(4) . . ?
C13 C12 P1 118.6(3) . . ?
C17 C12 P1 122.0(3) . . ?
C14 C13 C12 119.9(5) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C15 C14 C13 120.4(5) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 120.8(5) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C15 C16 C17 119.7(5) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
C16 C17 C12 120.0(4) . . ?
C16 C17 H17 120.0 . . ?
C12 C17 H17 120.0 . . ?
C23 C18 C19 118.3(4) . . ?
C23 C18 P1 121.9(3) . . ?
C19 C18 P1 119.7(3) . . ?
C20 C19 C18 120.6(4) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C21 C20 C19 120.3(4) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C22 C21 C20 119.5(4) . . ?
C22 C21 H21 120.3 . . ?
C20 C21 H21 120.3 . . ?
C21 C22 C23 121.1(4) . . ?
C21 C22 H22 119.4 . . ?
C23 C22 H22 119.4 . . ?
C18 C23 C22 120.1(4) . . ?
C18 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?

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
C18 P1 N1 C1 -106.7(3) . . . . ?
C12 P1 N1 C1 141.1(3) . . . . ?
S1 P1 N1 C1 17.4(3) . . . . ?
P1 N1 C1 C2 -129.0(3) . . . . ?
P1 N1 C1 C9 106.0(3) . . . . ?
N1 C1 C2 C3 36.5(5) . . . . ?
C9 C1 C2 C3 163.5(3) . . . . ?
N1 C1 C2 C7 -143.3(3) . . . . ?
C9 C1 C2 C7 -16.3(5) . . . . ?
C7 C2 C3 C4 0.4(6) . . . . ?
C1 C2 C3 C4 -179.4(3) . . . . ?
C2 C3 C4 C5 1.5(6) . . . . ?
C2 C3 C4 Br1 -179.4(3) . . . . ?
C3 C4 C5 C6 -1.8(6) . . . . ?
Br1 C4 C5 C6 179.0(3) . . . . ?
C4 C5 C6 C7 0.2(6) . . . . ?
C8 O1 C7 C6 165.2(3) . . . . ?
C8 O1 C7 C2 -16.2(5) . . . . ?
C5 C6 C7 O1 -179.7(4) . . . . ?
C5 C6 C7 C2 1.7(6) . . . . ?
C3 C2 C7 O1 179.5(3) . . . . ?
C1 C2 C7 O1 -0.7(5) . . . . ?
C3 C2 C7 C6 -2.0(5) . . . . ?
C1 C2 C7 C6 177.8(3) . . . . ?
C7 O1 C8 C9 49.6(4) . . . . ?
O1 C8 C9 C10 59.8(4) . . . . ?
O1 C8 C9 C1 -65.3(4) . . . . ?
N1 C1 C9 C10 49.2(4) . . . . ?
C2 C1 C9 C10 -76.1(4) . . . . ?
N1 C1 C9 C8 171.8(3) . . . . ?
C2 C1 C9 C8 46.5(4) . . . . ?
C8 C9 C10 O2 -101.6(4) . . . . ?
C1 C9 C10 O2 19.7(5) . . . . ?
C8 C9 C10 C11 77.8(4) . . . . ?
C1 C9 C10 C11 -160.9(4) . . . . ?
N1 P1 C12 C13 -92.8(3) . . . . ?
C18 P1 C12 C13 153.7(3) . . . . ?
S1 P1 C12 C13 31.1(3) . . . . ?
N1 P1 C12 C17 82.5(3) . . . . ?
C18 P1 C12 C17 -31.0(3) . . . . ?
S1 P1 C12 C17 -153.6(3) . . . . ?
C17 C12 C13 C14 0.6(6) . . . . ?
P1 C12 C13 C14 176.1(3) . . . . ?
C12 C13 C14 C15 0.1(7) . . . . ?
C13 C14 C15 C16 -0.9(7) . . . . ?
C14 C15 C16 C17 0.9(7) . . . . ?
C15 C16 C17 C12 -0.2(6) . . . . ?
C13 C12 C17 C16 -0.6(6) . . . . ?
P1 C12 C17 C16 -175.9(3) . . . . ?
N1 P1 C18 C23 -6.1(4) . . . . ?
C12 P1 C18 C23 104.4(3) . . . . ?
S1 P1 C18 C23 -131.6(3) . . . . ?
N1 P1 C18 C19 171.8(3) . . . . ?
C12 P1 C18 C19 -77.7(4) . . . . ?
S1 P1 C18 C19 46.3(4) . . . . ?
C23 C18 C19 C20 1.9(7) . . . . ?
P1 C18 C19 C20 -176.1(4) . . . . ?
C18 C19 C20 C21 0.1(8) . . . . ?
C19 C20 C21 C22 -1.8(8) . . . . ?
C20 C21 C22 C23 1.3(7) . . . . ?
C19 C18 C23 C22 -2.4(6) . . . . ?
P1 C18 C23 C22 175.6(3) . . . . ?
C21 C22 C23 C18 0.8(7) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O2 0.888(10) 2.126(11) 3.012(4) 175(3) 7_665

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        26.43
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.886
_refine_diff_density_min         -0.876
_refine_diff_density_rms         0.071