 
data_shelxl 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          'C24 H24 F N3 O3 S' 
_chemical_formula_sum 
 'C24 H24 F N3 O3 S' 
_chemical_formula_weight          453.52 
 
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' 
 'F'  'F'   0.0171   0.0103 
 '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' 
 'S'  'S'   0.1246   0.1234 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 
_symmetry_cell_setting            'triclinic' 
_symmetry_space_group_name_H-M    'P -1' 
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, -y, -z' 
 
_cell_length_a                    10.1760(7) 
_cell_length_b                    10.7150(6) 
_cell_length_c                    21.5609(18) 
_cell_angle_alpha                 99.229(6) 
_cell_angle_beta                  100.256(8) 
_cell_angle_gamma                 91.188(6) 
_cell_volume                      2280.5(3) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     150(1) 
_cell_measurement_reflns_used     41687
_cell_measurement_theta_min       1 
_cell_measurement_theta_max       27.5 
 
_exptl_crystal_description        'block' 
_exptl_crystal_colour             'colourless' 
_exptl_crystal_size_max           0.37 
_exptl_crystal_size_mid           0.17 
_exptl_crystal_size_min           0.16 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.321 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              952 
_exptl_absorpt_coefficient_mu     0.181 
# Absorption correction 

loop_
_exptl_crystal_face_index_h 
_exptl_crystal_face_index_k 
_exptl_crystal_face_index_l 
_exptl_crystal_face_perp_dist 
    1    0    1  0.019
   -1    0   -1  0.076
   -1    0    1  0.126
    1    0   -1  0.134
    0   -1    0  0.059
    0    1    0  0.076
    0    1   -1  0.094
    0    0   -1  0.156
    0    0    1  0.121


_exptl_absorpt_correction_type 'integration' 
_exptl_absorpt_correction_T_min  0.959
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details
;
Gaussian integration (Coppens, 1970)
;

 
_diffrn_ambient_temperature       150(1) 
_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   'Bruker Nonius KappaCCD area detector' 
_diffrn_measurement_method        'φ and ω scans to fill the Ewald sphere'  
_diffrn_detector_area_resol_mean  9.091
_diffrn_standards_number          0  
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             41644 
_diffrn_reflns_av_R_equivalents   0.0701 
_diffrn_reflns_av_sigmaI/netI     0.0630 
_diffrn_reflns_limit_h_min        -12 
_diffrn_reflns_limit_h_max        13 
_diffrn_reflns_limit_k_min        -13 
_diffrn_reflns_limit_k_max        13 
_diffrn_reflns_limit_l_min        -28 
_diffrn_reflns_limit_l_max        26 
_diffrn_reflns_theta_min          1.93 
_diffrn_reflns_theta_max          27.50 
_reflns_number_total              10323 
_reflns_number_gt                 6104 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        
'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)'
_computing_cell_refinement        'COLLECT and DENZO' 
_computing_data_reduction         'COLLECT and DENZO' 
_computing_structure_solution     'SIR92 (Altomare et al., 1994)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     'PLATON (Spek, 2003)'
_computing_publication_material   'SHELXL-97 (Sheldrick, 1997)'
 
_refine_special_details 
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) 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)+(0.0618P)²+7.9557P] 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_extinction_coef        ? 
_refine_ls_number_reflns          10323 
_refine_ls_number_parameters      577 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.1556 
_refine_ls_R_factor_gt            0.0915 
_refine_ls_wR_factor_ref          0.2338 
_refine_ls_wR_factor_gt           0.1922 
_refine_ls_goodness_of_fit_ref    1.079 
_refine_ls_restrained_S_all       1.079 
_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_symmetry_multiplicity 
 _atom_site_calc_flag 
 _atom_site_refinement_flags 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
S1 S 0.22069(12) 0.00541(12) 0.32898(6) 0.0384(3) Uani 1 1 d . . . 
S2 S 0.73082(12) 0.97059(11) 0.17722(6) 0.0359(3) Uani 1 1 d . . . 
O3 O 0.0633(3) 0.4194(3) 0.20857(14) 0.0304(7) Uani 1 1 d . . . 
O6 O 0.8761(3) 0.5577(3) 0.30024(14) 0.0303(7) Uani 1 1 d . . . 
O5 O 0.7459(3) 0.3138(3) 0.22588(14) 0.0329(7) Uani 1 1 d . . . 
O2 O 0.1983(3) 0.6630(3) 0.28091(15) 0.0327(7) Uani 1 1 d . . . 
O1 O 0.2267(3) 0.3694(3) 0.41413(14) 0.0312(7) Uani 1 1 d . . . 
C11 C 0.1873(4) 0.5657(4) 0.30115(19) 0.0234(9) Uani 1 1 d . . . 
N6 N 0.7260(3) 0.4320(3) 0.14386(15) 0.0229(7) Uani 1 1 d . . . 
O4 O 0.7367(3) 0.6055(3) 0.09250(14) 0.0318(7) Uani 1 1 d . . . 
C110 C 0.7580(4) 0.5579(4) 0.1396(2) 0.0240(9) Uani 1 1 d . . . 
N2 N 0.1320(3) 0.3585(3) 0.30693(16) 0.0253(8) Uani 1 1 d . . . 
C111 C 0.7624(4) 0.4098(4) 0.20575(19) 0.0236(9) Uani 1 1 d . . . 
N3 N 0.2349(3) 0.5427(3) 0.36189(16) 0.0225(7) Uani 1 1 d . . . 
N4 N 0.6051(4) 0.7733(4) 0.20660(18) 0.0399(11) Uani 1 1 d . . . 
C12 C 0.1174(4) 0.4402(4) 0.2635(2) 0.0246(9) Uani 1 1 d . . . 
N5 N 0.8199(3) 0.6171(3) 0.20074(16) 0.0248(7) Uani 1 1 d . . . 
C122 C 0.4404(4) 0.4681(4) 0.1145(2) 0.0259(9) Uani 1 1 d . . . 
H122 H 0.5100 0.5221 0.1448 0.031 Uiso 1 1 d R . . 
C113 C 0.6454(4) 0.3449(4) 0.09232(19) 0.0242(9) Uani 1 1 d . . . 
F2 F 0.2507(3) 1.1185(3) 0.12709(18) 0.0639(10) Uani 1 1 d . . . 
C7 C 0.2255(4) 0.1534(4) 0.3046(2) 0.0282(9) Uani 1 1 d . . . 
F1 F 0.7006(3) -0.1448(3) 0.37499(17) 0.0616(9) Uani 1 1 d . . . 
C13 C 0.3171(4) 0.6316(4) 0.41275(19) 0.0252(9) Uani 1 1 d . . . 
C10 C 0.2014(4) 0.4176(4) 0.3672(2) 0.0239(9) Uani 1 1 d . . . 
C103 C 0.5593(4) 0.9693(4) 0.1705(2) 0.0275(9) Uani 1 1 d . . . 
C107 C 0.7255(4) 0.8224(4) 0.20143(19) 0.0238(9) Uani 1 1 d . . . 
C8 C 0.0979(4) 0.2231(4) 0.2909(2) 0.0313(10) Uani 1 1 d . . . 
H8 H 0.0633 0.2032 0.2449 0.038 Uiso 1 1 d R . . 
C115 C 0.6271(5) 0.1632(4) 0.0112(2) 0.0341(10) Uani 1 1 d . . . 
H115 H 0.6650 0.0969 -0.0118 0.041 Uiso 1 1 d R . . 
C4 C 0.4409(5) 0.1150(4) 0.3168(2) 0.0305(10) Uani 1 1 d . . . 
C112 C 0.8279(4) 0.5363(4) 0.24404(19) 0.0227(8) Uani 1 1 d . . . 
C3 C 0.3920(4) 0.0052(4) 0.3343(2) 0.0283(9) Uani 1 1 d . . . 
C117 C 0.4319(4) 0.2720(4) 0.0307(2) 0.0286(9) Uani 1 1 d . . . 
H117 H 0.3400 0.2796 0.0202 0.034 Uiso 1 1 d R . . 
C118 C 0.5078(4) 0.3600(4) 0.07956(19) 0.0235(8) Uani 1 1 d . . . 
C18 C 0.2534(4) 0.7267(4) 0.4463(2) 0.0308(10) Uani 1 1 d . . . 
N1 N 0.3452(4) 0.2018(4) 0.29861(18) 0.0423(11) Uani 1 1 d . . . 
C14 C 0.4546(4) 0.6169(4) 0.4238(2) 0.0261(9) Uani 1 1 d . . . 
C108 C 0.8528(4) 0.7541(4) 0.2167(2) 0.0308(10) Uani 1 1 d . . . 
H108 H 0.8854 0.7746 0.2629 0.037 Uiso 1 1 d R . . 
C114 C 0.7090(4) 0.2472(4) 0.0586(2) 0.0303(10) Uani 1 1 d . . . 
C15 C 0.5310(5) 0.7059(4) 0.4717(2) 0.0331(10) Uani 1 1 d . . . 
H15 H 0.6232 0.6999 0.4811 0.040 Uiso 1 1 d R . . 
C21 C 0.5358(5) 0.5490(5) 0.3207(2) 0.0432(12) Uani 1 1 d . . . 
H21A H 0.4526 0.5765 0.2999 0.052 Uiso 1 1 d R . . 
H21B H 0.5627 0.4773 0.2939 0.052 Uiso 1 1 d R . . 
H21C H 0.6031 0.6166 0.3282 0.052 Uiso 1 1 d R . . 
C17 C 0.3352(5) 0.8150(5) 0.4922(2) 0.0386(11) Uani 1 1 d . . . 
H17 H 0.2977 0.8829 0.5142 0.046 Uiso 1 1 d R . . 
C19 C 0.5188(4) 0.5123(4) 0.3844(2) 0.0299(10) Uani 1 1 d . . . 
H19 H 0.4578 0.4369 0.3748 0.036 Uiso 1 1 d R . . 
C105 C 0.3751(5) 0.8401(5) 0.1853(2) 0.0399(12) Uani 1 1 d . . . 
H105 H 0.3421 0.7678 0.1973 0.048 Uiso 1 1 d R . . 
C2 C 0.4764(5) -0.0868(4) 0.3541(2) 0.0360(11) Uani 1 1 d . . . 
H2 H 0.4445 -0.1603 0.3655 0.043 Uiso 1 1 d R . . 
C116 C 0.4907(5) 0.1746(4) -0.0022(2) 0.0355(11) Uani 1 1 d . . . 
H116 H 0.4378 0.1161 -0.0339 0.043 Uiso 1 1 d R . . 
C9 C -0.0106(5) 0.1848(5) 0.3251(3) 0.0431(12) Uani 1 1 d . . . 
H9A H 0.0229 0.1987 0.3703 0.052 Uiso 1 1 d R . . 
H9B H -0.0364 0.0967 0.3107 0.052 Uiso 1 1 d R . . 
H9C H -0.0867 0.2347 0.3161 0.052 Uiso 1 1 d R . . 
C102 C 0.4753(5) 1.0619(4) 0.1499(2) 0.0378(11) Uani 1 1 d . . . 
H102 H 0.5075 1.1355 0.1387 0.045 Uiso 1 1 d R . . 
C106 C 0.2905(5) 0.9280(5) 0.1647(3) 0.0435(13) Uani 1 1 d . . . 
H106 H 0.1988 0.9157 0.1624 0.052 Uiso 1 1 d R . . 
C16 C 0.4718(5) 0.8029(5) 0.5046(2) 0.0404(12) Uani 1 1 d . . . 
H16 H 0.5249 0.8611 0.5362 0.049 Uiso 1 1 d R . . 
C101 C 0.3410(5) 1.0359(5) 0.1476(2) 0.0430(13) Uani 1 1 d . . . 
C6 C 0.6597(5) 0.0467(5) 0.3385(2) 0.0406(12) Uani 1 1 d . . . 
H6 H 0.7512 0.0595 0.3408 0.049 Uiso 1 1 d R . . 
C124 C 0.3429(6) 0.4198(5) 0.1523(3) 0.0481(14) Uani 1 1 d . . . 
H124A H 0.2705 0.3715 0.1231 0.058 Uiso 1 1 d R . . 
H124B H 0.3085 0.4901 0.1769 0.058 Uiso 1 1 d R . . 
H124C H 0.3881 0.3670 0.1804 0.058 Uiso 1 1 d R . . 
C104 C 0.5101(5) 0.8607(4) 0.1879(2) 0.0298(10) Uani 1 1 d . . . 
C22 C 0.1021(5) 0.7334(5) 0.4361(2) 0.0383(11) Uani 1 1 d . . . 
H22 H 0.0660 0.6999 0.3911 0.046 Uiso 1 1 d R . . 
C119 C 0.8599(5) 0.2389(5) 0.0718(2) 0.0409(12) Uani 1 1 d . . . 
H119 H 0.8914 0.2656 0.1178 0.049 Uiso 1 1 d R . . 
C5 C 0.5757(5) 0.1346(5) 0.3188(2) 0.0394(12) Uani 1 1 d . . . 
H5 H 0.6083 0.2070 0.3067 0.047 Uiso 1 1 d R . . 
C1 C 0.6103(5) -0.0620(5) 0.3556(2) 0.0449(13) Uani 1 1 d . . . 
C20 C 0.6528(5) 0.4761(5) 0.4195(3) 0.0435(12) Uani 1 1 d . . . 
H20A H 0.7168 0.5463 0.4267 0.052 Uiso 1 1 d R . . 
H20B H 0.6839 0.4049 0.3939 0.052 Uiso 1 1 d R . . 
H20C H 0.6418 0.4539 0.4597 0.052 Uiso 1 1 d R . . 
C109 C 0.9635(5) 0.7928(5) 0.1835(3) 0.0414(12) Uani 1 1 d . . . 
H109A H 1.0398 0.7437 0.1937 0.050 Uiso 1 1 d R . . 
H109B H 0.9882 0.8811 0.1979 0.050 Uiso 1 1 d R . . 
H109C H 0.9325 0.7782 0.1381 0.050 Uiso 1 1 d R . . 
C123 C 0.3703(6) 0.5477(5) 0.0680(2) 0.0496(14) Uani 1 1 d . . . 
H123A H 0.4331 0.5777 0.0446 0.060 Uiso 1 1 d R . . 
H123B H 0.3334 0.6186 0.0910 0.060 Uiso 1 1 d R . . 
H123C H 0.2997 0.4971 0.0387 0.060 Uiso 1 1 d R . . 
C120 C 0.9036(6) 0.1046(6) 0.0540(3) 0.0645(17) Uani 1 1 d . . . 
H120A H 0.8964 0.0847 0.0084 0.077 Uiso 1 1 d R . . 
H120B H 0.8470 0.0461 0.0678 0.077 Uiso 1 1 d R . . 
H120C H 0.9946 0.0985 0.0743 0.077 Uiso 1 1 d R . . 
C121 C 0.9248(6) 0.3280(7) 0.0379(4) 0.076(2) Uani 1 1 d . . . 
H121A H 0.9071 0.2963 -0.0072 0.092 Uiso 1 1 d R . . 
H121B H 1.0196 0.3347 0.0533 0.092 Uiso 1 1 d R . . 
H121C H 0.8889 0.4100 0.0457 0.092 Uiso 1 1 d R . . 
C24 C 0.0538(7) 0.8655(7) 0.4511(5) 0.090(3) Uani 1 1 d . . . 
H24A H 0.0572 0.8873 0.4964 0.108 Uiso 1 1 d R . . 
H24B H -0.0365 0.8684 0.4291 0.108 Uiso 1 1 d R . . 
H24C H 0.1103 0.9246 0.4375 0.108 Uiso 1 1 d R . . 
C23 C 0.0477(7) 0.6507(8) 0.4755(4) 0.091(3) Uani 1 1 d . . . 
H23A H 0.0898 0.5712 0.4717 0.109 Uiso 1 1 d R . . 
H23B H -0.0471 0.6364 0.4612 0.109 Uiso 1 1 d R . . 
H23C H 0.0655 0.6915 0.5194 0.109 Uiso 1 1 d R . . 
 
 
_geom_special_details 
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
; 
 
loop_ 
 _geom_bond_atom_site_label_1 
 _geom_bond_atom_site_label_2 
 _geom_bond_distance 
 _geom_bond_site_symmetry_2 
 _geom_bond_publ_flag 
S1 C3 1.727(4) . ? 
S1 C7 1.751(4) . ? 
S2 C103 1.726(4) . ? 
S2 C107 1.751(4) . ? 
O3 C12 1.197(5) . ? 
O6 C112 1.207(5) . ? 
O5 C111 1.198(5) . ? 
O2 C11 1.203(5) . ? 
O1 C10 1.199(5) . ? 
C11 N3 1.376(5) . ? 
C11 C12 1.542(6) . ? 
N6 C111 1.380(5) . ? 
N6 C110 1.403(5) . ? 
N6 C113 1.446(5) . ? 
O4 C110 1.195(5) . ? 
C110 N5 1.399(5) . ? 
N2 C12 1.373(5) . ? 
N2 C10 1.407(5) . ? 
N2 C8 1.457(5) . ? 
C111 C112 1.540(6) . ? 
N3 C10 1.404(5) . ? 
N3 C13 1.454(5) . ? 
N4 C107 1.353(6) . ? 
N4 C104 1.413(6) . ? 
N5 C112 1.365(5) . ? 
N5 C108 1.470(5) . ? 
C122 C123 1.513(6) . ? 
C122 C124 1.521(6) . ? 
C122 C118 1.522(6) . ? 
C122 H122 0.9800 . ? 
C113 C118 1.396(6) . ? 
C113 C114 1.412(6) . ? 
F2 C101 1.355(5) . ? 
C7 N1 1.350(6) . ? 
C7 C8 1.518(6) . ? 
F1 C1 1.350(5) . ? 
C13 C14 1.393(6) . ? 
C13 C18 1.394(6) . ? 
C103 C104 1.388(6) . ? 
C103 C102 1.398(6) . ? 
C107 C108 1.513(6) . ? 
C8 C9 1.516(6) . ? 
C8 H8 0.9799 . ? 
C115 C116 1.379(7) . ? 
C115 C114 1.385(6) . ? 
C115 H115 0.9300 . ? 
C4 C5 1.375(6) . ? 
C4 C3 1.400(6) . ? 
C4 N1 1.409(6) . ? 
C3 C2 1.390(6) . ? 
C117 C116 1.375(6) . ? 
C117 C118 1.399(6) . ? 
C117 H117 0.9300 . ? 
C18 C17 1.393(6) . ? 
C18 C22 1.520(6) . ? 
C14 C15 1.395(6) . ? 
C14 C19 1.526(6) . ? 
C108 C109 1.521(7) . ? 
C108 H108 0.9799 . ? 
C114 C119 1.519(6) . ? 
C15 C16 1.374(7) . ? 
C15 H15 0.9300 . ? 
C21 C19 1.527(6) . ? 
C21 H21A 0.9599 . ? 
C21 H21B 0.9600 . ? 
C21 H21C 0.9600 . ? 
C17 C16 1.381(7) . ? 
C17 H17 0.9299 . ? 
C19 C20 1.526(6) . ? 
C19 H19 0.9800 . ? 
C105 C106 1.362(7) . ? 
C105 C104 1.376(7) . ? 
C105 H105 0.9301 . ? 
C2 C1 1.376(7) . ? 
C2 H2 0.9300 . ? 
C116 H116 0.9301 . ? 
C9 H9A 0.9601 . ? 
C9 H9B 0.9601 . ? 
C9 H9C 0.9598 . ? 
C102 C101 1.380(7) . ? 
C102 H102 0.9302 . ? 
C106 C101 1.385(8) . ? 
C106 H106 0.9300 . ? 
C16 H16 0.9299 . ? 
C6 C5 1.353(7) . ? 
C6 C1 1.388(8) . ? 
C6 H6 0.9300 . ? 
C124 H124A 0.9600 . ? 
C124 H124B 0.9600 . ? 
C124 H124C 0.9599 . ? 
C22 C23 1.484(8) . ? 
C22 C24 1.513(8) . ? 
C22 H22 0.9800 . ? 
C119 C121 1.501(8) . ? 
C119 C120 1.525(7) . ? 
C119 H119 0.9799 . ? 
C5 H5 0.9300 . ? 
C20 H20A 0.9600 . ? 
C20 H20B 0.9600 . ? 
C20 H20C 0.9599 . ? 
C109 H109A 0.9600 . ? 
C109 H109B 0.9600 . ? 
C109 H109C 0.9605 . ? 
C123 H123A 0.9600 . ? 
C123 H123B 0.9600 . ? 
C123 H123C 0.9600 . ? 
C120 H120A 0.9599 . ? 
C120 H120B 0.9600 . ? 
C120 H120C 0.9601 . ? 
C121 H121A 0.9601 . ? 
C121 H121B 0.9597 . ? 
C121 H121C 0.9601 . ? 
C24 H24A 0.9599 . ? 
C24 H24B 0.9601 . ? 
C24 H24C 0.9600 . ? 
C23 H23A 0.9600 . ? 
C23 H23B 0.9600 . ? 
C23 H23C 0.9601 . ? 
 
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 S1 C7 88.1(2) . . ? 
C103 S2 C107 87.9(2) . . ? 
O2 C11 N3 127.6(4) . . ? 
O2 C11 C12 126.5(4) . . ? 
N3 C11 C12 105.9(3) . . ? 
C111 N6 C110 111.1(3) . . ? 
C111 N6 C113 124.7(3) . . ? 
C110 N6 C113 123.4(3) . . ? 
O4 C110 N5 126.5(4) . . ? 
O4 C110 N6 126.5(4) . . ? 
N5 C110 N6 107.0(3) . . ? 
C12 N2 C10 111.7(3) . . ? 
C12 N2 C8 124.4(4) . . ? 
C10 N2 C8 123.3(3) . . ? 
O5 C111 N6 128.0(4) . . ? 
O5 C111 C112 127.1(4) . . ? 
N6 C111 C112 104.9(3) . . ? 
C11 N3 C10 110.7(3) . . ? 
C11 N3 C13 125.2(3) . . ? 
C10 N3 C13 123.9(3) . . ? 
C107 N4 C104 106.4(4) . . ? 
O3 C12 N2 128.1(4) . . ? 
O3 C12 C11 127.4(4) . . ? 
N2 C12 C11 104.5(3) . . ? 
C112 N5 C110 111.8(3) . . ? 
C112 N5 C108 125.0(4) . . ? 
C110 N5 C108 122.6(3) . . ? 
C123 C122 C124 110.6(4) . . ? 
C123 C122 C118 110.5(4) . . ? 
C124 C122 C118 111.7(4) . . ? 
C123 C122 H122 108.0 . . ? 
C124 C122 H122 107.9 . . ? 
C118 C122 H122 108.1 . . ? 
C118 C113 C114 123.4(4) . . ? 
C118 C113 N6 118.0(4) . . ? 
C114 C113 N6 118.6(4) . . ? 
N1 C7 C8 122.0(4) . . ? 
N1 C7 S1 117.8(3) . . ? 
C8 C7 S1 120.2(3) . . ? 
C14 C13 C18 124.5(4) . . ? 
C14 C13 N3 117.7(4) . . ? 
C18 C13 N3 117.8(4) . . ? 
O1 C10 N3 126.8(4) . . ? 
O1 C10 N2 126.0(4) . . ? 
N3 C10 N2 107.2(3) . . ? 
C104 C103 C102 122.0(4) . . ? 
C104 C103 S2 111.3(3) . . ? 
C102 C103 S2 126.7(4) . . ? 
N4 C107 C108 121.9(4) . . ? 
N4 C107 S2 117.9(3) . . ? 
C108 C107 S2 120.2(3) . . ? 
N2 C8 C9 111.7(4) . . ? 
N2 C8 C7 108.2(3) . . ? 
C9 C8 C7 113.6(4) . . ? 
N2 C8 H8 107.8 . . ? 
C9 C8 H8 107.7 . . ? 
C7 C8 H8 107.7 . . ? 
C116 C115 C114 121.6(4) . . ? 
C116 C115 H115 119.2 . . ? 
C114 C115 H115 119.2 . . ? 
C5 C4 C3 120.3(4) . . ? 
C5 C4 N1 123.5(4) . . ? 
C3 C4 N1 116.2(4) . . ? 
O6 C112 N5 128.1(4) . . ? 
O6 C112 C111 126.7(4) . . ? 
N5 C112 C111 105.2(3) . . ? 
C2 C3 C4 121.8(4) . . ? 
C2 C3 S1 127.2(4) . . ? 
C4 C3 S1 111.0(3) . . ? 
C116 C117 C118 121.2(4) . . ? 
C116 C117 H117 119.4 . . ? 
C118 C117 H117 119.4 . . ? 
C113 C118 C117 116.8(4) . . ? 
C113 C118 C122 123.1(4) . . ? 
C117 C118 C122 120.1(4) . . ? 
C17 C18 C13 116.7(4) . . ? 
C17 C18 C22 120.6(4) . . ? 
C13 C18 C22 122.7(4) . . ? 
C7 N1 C4 106.9(4) . . ? 
C13 C14 C15 116.2(4) . . ? 
C13 C14 C19 122.0(4) . . ? 
C15 C14 C19 121.7(4) . . ? 
N5 C108 C107 108.3(3) . . ? 
N5 C108 C109 111.6(4) . . ? 
C107 C108 C109 113.6(4) . . ? 
N5 C108 H108 107.7 . . ? 
C107 C108 H108 107.7 . . ? 
C109 C108 H108 107.7 . . ? 
C115 C114 C113 116.5(4) . . ? 
C115 C114 C119 122.0(4) . . ? 
C113 C114 C119 121.4(4) . . ? 
C16 C15 C14 120.8(4) . . ? 
C16 C15 H15 119.6 . . ? 
C14 C15 H15 119.5 . . ? 
C19 C21 H21A 109.6 . . ? 
C19 C21 H21B 109.6 . . ? 
H21A C21 H21B 109.5 . . ? 
C19 C21 H21C 109.3 . . ? 
H21A C21 H21C 109.5 . . ? 
H21B C21 H21C 109.5 . . ? 
C16 C17 C18 120.2(4) . . ? 
C16 C17 H17 119.9 . . ? 
C18 C17 H17 119.8 . . ? 
C14 C19 C20 113.3(4) . . ? 
C14 C19 C21 110.9(4) . . ? 
C20 C19 C21 109.8(4) . . ? 
C14 C19 H19 107.7 . . ? 
C20 C19 H19 107.6 . . ? 
C21 C19 H19 107.3 . . ? 
C106 C105 C104 118.6(5) . . ? 
C106 C105 H105 120.5 . . ? 
C104 C105 H105 120.8 . . ? 
C1 C2 C3 115.5(4) . . ? 
C1 C2 H2 122.3 . . ? 
C3 C2 H2 122.2 . . ? 
C117 C116 C115 120.5(4) . . ? 
C117 C116 H116 119.6 . . ? 
C115 C116 H116 119.9 . . ? 
C8 C9 H9A 109.3 . . ? 
C8 C9 H9B 109.6 . . ? 
H9A C9 H9B 109.5 . . ? 
C8 C9 H9C 109.5 . . ? 
H9A C9 H9C 109.5 . . ? 
H9B C9 H9C 109.5 . . ? 
C101 C102 C103 114.8(4) . . ? 
C101 C102 H102 122.6 . . ? 
C103 C102 H102 122.6 . . ? 
C105 C106 C101 120.0(5) . . ? 
C105 C106 H106 120.0 . . ? 
C101 C106 H106 120.0 . . ? 
C15 C16 C17 121.5(4) . . ? 
C15 C16 H16 119.2 . . ? 
C17 C16 H16 119.3 . . ? 
F2 C101 C102 119.6(5) . . ? 
F2 C101 C106 116.6(5) . . ? 
C102 C101 C106 123.8(5) . . ? 
C5 C6 C1 120.5(5) . . ? 
C5 C6 H6 119.7 . . ? 
C1 C6 H6 119.8 . . ? 
C122 C124 H124A 109.2 . . ? 
C122 C124 H124B 109.7 . . ? 
H124A C124 H124B 109.5 . . ? 
C122 C124 H124C 109.5 . . ? 
H124A C124 H124C 109.5 . . ? 
H124B C124 H124C 109.5 . . ? 
C105 C104 C103 120.8(4) . . ? 
C105 C104 N4 122.8(4) . . ? 
C103 C104 N4 116.5(4) . . ? 
C23 C22 C24 109.2(5) . . ? 
C23 C22 C18 109.3(5) . . ? 
C24 C22 C18 114.3(5) . . ? 
C23 C22 H22 107.8 . . ? 
C24 C22 H22 108.0 . . ? 
C18 C22 H22 108.0 . . ? 
C121 C119 C114 110.6(4) . . ? 
C121 C119 C120 110.3(5) . . ? 
C114 C119 C120 112.6(5) . . ? 
C121 C119 H119 107.7 . . ? 
C114 C119 H119 107.8 . . ? 
C120 C119 H119 107.7 . . ? 
C6 C5 C4 118.9(5) . . ? 
C6 C5 H5 120.7 . . ? 
C4 C5 H5 120.4 . . ? 
F1 C1 C2 120.1(5) . . ? 
F1 C1 C6 116.9(5) . . ? 
C2 C1 C6 123.1(5) . . ? 
C19 C20 H20A 109.6 . . ? 
C19 C20 H20B 109.3 . . ? 
H20A C20 H20B 109.5 . . ? 
C19 C20 H20C 109.5 . . ? 
H20A C20 H20C 109.5 . . ? 
H20B C20 H20C 109.5 . . ? 
C108 C109 H109A 109.4 . . ? 
C108 C109 H109B 109.5 . . ? 
H109A C109 H109B 109.5 . . ? 
C108 C109 H109C 109.6 . . ? 
H109A C109 H109C 109.4 . . ? 
H109B C109 H109C 109.5 . . ? 
C122 C123 H123A 109.6 . . ? 
C122 C123 H123B 109.5 . . ? 
H123A C123 H123B 109.5 . . ? 
C122 C123 H123C 109.3 . . ? 
H123A C123 H123C 109.5 . . ? 
H123B C123 H123C 109.5 . . ? 
C119 C120 H120A 109.3 . . ? 
C119 C120 H120B 109.4 . . ? 
H120A C120 H120B 109.5 . . ? 
C119 C120 H120C 109.6 . . ? 
H120A C120 H120C 109.5 . . ? 
H120B C120 H120C 109.5 . . ? 
C119 C121 H121A 109.3 . . ? 
C119 C121 H121B 109.7 . . ? 
H121A C121 H121B 109.5 . . ? 
C119 C121 H121C 109.4 . . ? 
H121A C121 H121C 109.5 . . ? 
H121B C121 H121C 109.5 . . ? 
C22 C24 H24A 109.4 . . ? 
C22 C24 H24B 109.6 . . ? 
H24A C24 H24B 109.5 . . ? 
C22 C24 H24C 109.4 . . ? 
H24A C24 H24C 109.5 . . ? 
H24B C24 H24C 109.5 . . ? 
C22 C23 H23A 109.6 . . ? 
C22 C23 H23B 109.8 . . ? 
H23A C23 H23B 109.5 . . ? 
C22 C23 H23C 109.1 . . ? 
H23A C23 H23C 109.5 . . ? 
H23B C23 H23C 109.5 . . ? 
 
_diffrn_measured_fraction_theta_max    0.986 
_diffrn_reflns_theta_full              27.50 
_diffrn_measured_fraction_theta_full   0.986 
_refine_diff_density_max    1.295 
_refine_diff_density_min   -0.538 
_refine_diff_density_rms    0.082 
