 
data_01src322
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C33 H25 F3 N O2 P Pd' 
_chemical_formula_weight          661.91 
 
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' 
 'F'  'F'   0.0171   0.0103 
 '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' 
 'Pd'  'Pd'  -0.9988   1.0072 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 
_symmetry_cell_setting            Monoclinic 
_symmetry_space_group_name_H-M    P2(1)/c 
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, y+1/2, -z+1/2' 
 '-x, -y, -z' 
 'x, -y-1/2, z-1/2' 
 
_cell_length_a                    9.911(2) 
_cell_length_b                    29.932(6) 
_cell_length_c                    9.907(2) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  104.20(3) 
_cell_angle_gamma                 90.00 
_cell_volume                      2849.3(10) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     150(2) 
_cell_measurement_reflns_used     14475
_cell_measurement_theta_min       2.94
_cell_measurement_theta_max       26.00
 
_exptl_crystal_description        Block 
_exptl_crystal_colour             yellow 
_exptl_crystal_size_max           0.50 
_exptl_crystal_size_mid           0.15 
_exptl_crystal_size_min           0.02 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.543 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              1336 
_exptl_absorpt_coefficient_mu     0.759 
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.7029 
_exptl_absorpt_correction_T_max   0.9850 
_exptl_absorpt_process_details    'SORTAV (Blessing, 1997)'
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       150(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'Bruker-Nonius FR591 rotating anode' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Bruker-Nonius KappaCCD'
_diffrn_measurement_method        'Φ & ω scans'
_diffrn_detector_area_resol_mean  9.091
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             14475 
_diffrn_reflns_av_R_equivalents   0.0868 
_diffrn_reflns_av_sigmaI/netI     0.0683 
_diffrn_reflns_limit_h_min        -10 
_diffrn_reflns_limit_h_max        12 
_diffrn_reflns_limit_k_min        -33 
_diffrn_reflns_limit_k_max        36 
_diffrn_reflns_limit_l_min        -12 
_diffrn_reflns_limit_l_max        9 
_diffrn_reflns_theta_min          2.94 
_diffrn_reflns_theta_max          26.00 
_reflns_number_total              5317 
_reflns_number_gt                 4675 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        'COLLECT (Hooft, 1998)'
_computing_cell_refinement        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)'
_computing_data_reduction         
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)'
_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 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)+(0.0580P)²+1.7947P] where P=(Fo²+2Fc²)/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      SHELXL 
_refine_ls_extinction_coef        0.0010(5) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^' 
_refine_ls_number_reflns          5317 
_refine_ls_number_parameters      396 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0493 
_refine_ls_R_factor_gt            0.0429 
_refine_ls_wR_factor_ref          0.1188 
_refine_ls_wR_factor_gt           0.1154 
_refine_ls_goodness_of_fit_ref    1.098 
_refine_ls_restrained_S_all       1.098 
_refine_ls_shift/su_max           0.016 
_refine_ls_shift/su_mean          0.002 
 
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 
Pd1 Pd 0.20873(2) 0.164766(7) 0.43763(2) 0.01575(12) Uani 1 1 d . . . 
P1 P 0.30991(9) 0.09713(3) 0.47456(8) 0.01532(19) Uani 1 1 d . . . 
F1 F -0.1684(4) 0.15083(14) 0.0324(4) 0.1088(16) Uani 1 1 d . . . 
F2 F -0.1242(4) 0.08435(12) 0.0787(3) 0.0879(12) Uani 1 1 d . . . 
F3 F -0.0492(3) 0.11455(12) -0.0777(2) 0.0674(9) Uani 1 1 d . . . 
O1 O 0.0432(2) 0.14077(8) 0.2749(2) 0.0217(5) Uani 1 1 d . . . 
O2 O 0.1714(3) 0.13996(8) 0.1165(2) 0.0285(6) Uani 1 1 d . . . 
N1 N 0.1287(3) 0.23084(9) 0.4154(3) 0.0198(6) Uani 1 1 d . . . 
C1 C 0.1958(4) 0.25617(11) 0.5150(3) 0.0237(7) Uani 1 1 d . . . 
H1 H 0.1686 0.2864 0.5214 0.025(9) Uiso 1 1 calc R . . 
C2 C 0.3126(4) 0.23783(11) 0.6162(3) 0.0212(7) Uani 1 1 d . . . 
C3 C 0.3478(3) 0.19305(11) 0.5957(3) 0.0201(7) Uani 1 1 d . . . 
C4 C 0.4672(4) 0.17690(12) 0.6895(3) 0.0247(8) Uani 1 1 d . . . 
H4 H 0.4984 0.1475 0.6779 0.025(9) Uiso 1 1 calc R . . 
C5 C 0.5415(4) 0.20284(13) 0.7994(4) 0.0302(8) Uani 1 1 d . . . 
H5 H 0.6225 0.1909 0.8608 0.027(10) Uiso 1 1 calc R . . 
C6 C 0.4993(4) 0.24565(13) 0.8206(4) 0.0327(9) Uani 1 1 d . . . 
H6 H 0.5481 0.2626 0.8985 0.028(10) Uiso 1 1 calc R . . 
C7 C 0.3856(4) 0.26361(12) 0.7274(4) 0.0299(8) Uani 1 1 d . . . 
H7 H 0.3571 0.2934 0.7390 0.025(9) Uiso 1 1 calc R . . 
C8 C 0.0634(3) 0.13553(10) 0.1555(3) 0.0202(7) Uani 1 1 d . . . 
C9 C -0.0685(4) 0.12206(12) 0.0462(3) 0.0275(8) Uani 1 1 d . . . 
C10 C 0.0218(3) 0.25109(11) 0.3084(3) 0.0203(7) Uani 1 1 d . . . 
C11 C -0.1054(4) 0.23011(12) 0.2613(3) 0.0245(7) Uani 1 1 d . . . 
H11 H -0.1220 0.2019 0.2981 0.010(8) Uiso 1 1 calc R . . 
C12 C -0.2077(4) 0.25044(13) 0.1607(4) 0.0311(8) Uani 1 1 d . . . 
H12 H -0.2950 0.2360 0.1282 0.043(12) Uiso 1 1 calc R . . 
C13 C -0.1850(4) 0.29186(13) 0.1059(4) 0.0333(9) Uani 1 1 d . . . 
H13 H -0.2564 0.3059 0.0375 0.055(13) Uiso 1 1 calc R . . 
C14 C -0.0569(4) 0.31214(13) 0.1529(4) 0.0332(9) Uani 1 1 d . . . 
H14 H -0.0397 0.3402 0.1157 0.058(15) Uiso 1 1 calc R . . 
C15 C 0.0460(4) 0.29200(12) 0.2531(4) 0.0267(8) Uani 1 1 d . . . 
H15 H 0.1339 0.3062 0.2845 0.023(9) Uiso 1 1 calc R . . 
C20 C 0.2102(3) 0.05365(11) 0.3648(3) 0.0178(7) Uani 1 1 d . . . 
C21 C 0.2568(4) 0.03024(11) 0.2644(3) 0.0240(8) Uani 1 1 d . . . 
H21 H 0.3453 0.0368 0.2482 0.038(11) Uiso 1 1 calc R . . 
C22 C 0.1741(4) -0.00277(13) 0.1874(4) 0.0330(9) Uani 1 1 d . . . 
H22 H 0.2066 -0.0188 0.1188 0.060(14) Uiso 1 1 calc R . . 
C23 C 0.0446(4) -0.01263(13) 0.2097(4) 0.0321(9) Uani 1 1 d . . . 
H23 H -0.0116 -0.0352 0.1563 0.035(11) Uiso 1 1 calc R . . 
C24 C -0.0023(4) 0.01045(12) 0.3097(4) 0.0287(8) Uani 1 1 d . . . 
H24 H -0.0909 0.0038 0.3254 0.026(9) Uiso 1 1 calc R . . 
C25 C 0.0793(3) 0.04320(12) 0.3868(3) 0.0234(7) Uani 1 1 d . . . 
H25 H 0.0465 0.0589 0.4557 0.025(9) Uiso 1 1 calc R . . 
C30 C 0.4811(3) 0.09706(10) 0.4376(3) 0.0176(7) Uani 1 1 d . . . 
C31 C 0.6019(3) 0.08133(11) 0.5292(3) 0.0222(7) Uani 1 1 d . . . 
H31 H 0.5972 0.0682 0.6152 0.026(10) Uiso 1 1 calc R . . 
C32 C 0.7294(4) 0.08485(12) 0.4945(4) 0.0268(8) Uani 1 1 d . . . 
H32 H 0.8112 0.0738 0.5569 0.049(13) Uiso 1 1 calc R . . 
C33 C 0.7383(4) 0.10431(12) 0.3700(4) 0.0299(8) Uani 1 1 d . . . 
H33 H 0.8258 0.1069 0.3475 0.059(14) Uiso 1 1 calc R . . 
C34 C 0.6189(4) 0.11984(12) 0.2792(4) 0.0278(8) Uani 1 1 d . . . 
H34 H 0.6246 0.1331 0.1936 0.043(12) Uiso 1 1 calc R . . 
C35 C 0.4898(4) 0.11628(11) 0.3116(3) 0.0235(7) Uani 1 1 d . . . 
H35 H 0.4082 0.1269 0.2480 0.030(10) Uiso 1 1 calc R . . 
C40 C 0.3274(3) 0.07203(11) 0.6453(3) 0.0173(7) Uani 1 1 d . . . 
C41 C 0.2829(4) 0.09456(11) 0.7498(3) 0.0229(7) Uani 1 1 d . . . 
H41 H 0.2459 0.1239 0.7329 0.021(9) Uiso 1 1 calc R . . 
C42 C 0.2922(4) 0.07473(13) 0.8775(3) 0.0292(8) Uani 1 1 d . . . 
H42 H 0.2627 0.0904 0.9486 0.026(10) Uiso 1 1 calc R . . 
C43 C 0.3448(4) 0.03180(14) 0.9013(3) 0.0311(9) Uani 1 1 d . . . 
H43 H 0.3521 0.0182 0.9894 0.021(9) Uiso 1 1 calc R . . 
C44 C 0.3866(4) 0.00869(12) 0.7981(3) 0.0258(8) Uani 1 1 d . . . 
H44 H 0.4220 -0.0208 0.8151 0.023(9) Uiso 1 1 calc R . . 
C45 C 0.3768(3) 0.02852(11) 0.6695(3) 0.0214(7) Uani 1 1 d . . . 
H45 H 0.4039 0.0124 0.5979 0.021(9) Uiso 1 1 calc 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 
Pd1 C3 2.003(3) . ? 
Pd1 N1 2.122(3) . ? 
Pd1 O1 2.124(2) . ? 
Pd1 P1 2.2489(9) . ? 
P1 C30 1.821(3) . ? 
P1 C40 1.820(3) . ? 
P1 C20 1.823(3) . ? 
F1 C9 1.294(5) . ? 
F2 C9 1.330(5) . ? 
F3 C9 1.308(4) . ? 
O1 C8 1.257(4) . ? 
O2 C8 1.232(4) . ? 
N1 C1 1.292(4) . ? 
N1 C10 1.436(4) . ? 
C1 C2 1.441(5) . ? 
C1 H1 0.9500 . ? 
C2 C7 1.393(5) . ? 
C2 C3 1.412(5) . ? 
C3 C4 1.399(5) . ? 
C4 C5 1.392(5) . ? 
C4 H4 0.9500 . ? 
C5 C6 1.380(5) . ? 
C5 H5 0.9500 . ? 
C6 C7 1.380(5) . ? 
C6 H6 0.9500 . ? 
C7 H7 0.9500 . ? 
C8 C9 1.533(5) . ? 
C10 C15 1.386(5) . ? 
C10 C11 1.383(5) . ? 
C11 C12 1.377(5) . ? 
C11 H11 0.9500 . ? 
C12 C13 1.394(5) . ? 
C12 H12 0.9500 . ? 
C13 C14 1.381(6) . ? 
C13 H13 0.9500 . ? 
C14 C15 1.375(5) . ? 
C14 H14 0.9500 . ? 
C15 H15 0.9500 . ? 
C20 C21 1.386(4) . ? 
C20 C25 1.403(4) . ? 
C21 C22 1.386(5) . ? 
C21 H21 0.9500 . ? 
C22 C23 1.387(5) . ? 
C22 H22 0.9500 . ? 
C23 C24 1.379(5) . ? 
C23 H23 0.9500 . ? 
C24 C25 1.377(5) . ? 
C24 H24 0.9500 . ? 
C25 H25 0.9500 . ? 
C30 C35 1.396(4) . ? 
C30 C31 1.395(5) . ? 
C31 C32 1.392(5) . ? 
C31 H31 0.9500 . ? 
C32 C33 1.386(5) . ? 
C32 H32 0.9500 . ? 
C33 C34 1.380(5) . ? 
C33 H33 0.9500 . ? 
C34 C35 1.398(5) . ? 
C34 H34 0.9500 . ? 
C35 H35 0.9500 . ? 
C40 C45 1.391(5) . ? 
C40 C41 1.395(4) . ? 
C41 C42 1.380(5) . ? 
C41 H41 0.9500 . ? 
C42 C43 1.385(5) . ? 
C42 H42 0.9500 . ? 
C43 C44 1.379(5) . ? 
C43 H43 0.9500 . ? 
C44 C45 1.388(5) . ? 
C44 H44 0.9500 . ? 
C45 H45 0.9500 . ? 
 
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 Pd1 N1 81.67(12) . . ? 
C3 Pd1 O1 172.80(11) . . ? 
N1 Pd1 O1 92.12(10) . . ? 
C3 Pd1 P1 93.41(10) . . ? 
N1 Pd1 P1 175.00(8) . . ? 
O1 Pd1 P1 92.85(7) . . ? 
C30 P1 C40 107.78(15) . . ? 
C30 P1 C20 105.93(14) . . ? 
C40 P1 C20 100.00(15) . . ? 
C30 P1 Pd1 111.62(10) . . ? 
C40 P1 Pd1 117.38(11) . . ? 
C20 P1 Pd1 113.00(11) . . ? 
C8 O1 Pd1 119.0(2) . . ? 
C1 N1 C10 117.7(3) . . ? 
C1 N1 Pd1 111.0(2) . . ? 
C10 N1 Pd1 131.2(2) . . ? 
N1 C1 C2 118.9(3) . . ? 
N1 C1 H1 120.6 . . ? 
C2 C1 H1 120.6 . . ? 
C7 C2 C3 122.7(3) . . ? 
C7 C2 C1 120.8(3) . . ? 
C3 C2 C1 116.5(3) . . ? 
C4 C3 C2 115.5(3) . . ? 
C4 C3 Pd1 132.9(3) . . ? 
C2 C3 Pd1 111.5(2) . . ? 
C5 C4 C3 121.7(3) . . ? 
C5 C4 H4 119.1 . . ? 
C3 C4 H4 119.1 . . ? 
C6 C5 C4 121.0(3) . . ? 
C6 C5 H5 119.5 . . ? 
C4 C5 H5 119.5 . . ? 
C5 C6 C7 119.2(3) . . ? 
C5 C6 H6 120.4 . . ? 
C7 C6 H6 120.4 . . ? 
C6 C7 C2 119.6(3) . . ? 
C6 C7 H7 120.2 . . ? 
C2 C7 H7 120.2 . . ? 
O2 C8 O1 129.3(3) . . ? 
O2 C8 C9 117.6(3) . . ? 
O1 C8 C9 113.1(3) . . ? 
F1 C9 F3 107.4(3) . . ? 
F1 C9 F2 103.8(4) . . ? 
F3 C9 F2 104.2(3) . . ? 
F1 C9 C8 113.4(3) . . ? 
F3 C9 C8 114.4(3) . . ? 
F2 C9 C8 112.6(3) . . ? 
C15 C10 C11 120.0(3) . . ? 
C15 C10 N1 119.8(3) . . ? 
C11 C10 N1 120.2(3) . . ? 
C12 C11 C10 119.5(3) . . ? 
C12 C11 H11 120.3 . . ? 
C10 C11 H11 120.3 . . ? 
C11 C12 C13 121.0(4) . . ? 
C11 C12 H12 119.5 . . ? 
C13 C12 H12 119.5 . . ? 
C14 C13 C12 118.9(4) . . ? 
C14 C13 H13 120.6 . . ? 
C12 C13 H13 120.6 . . ? 
C15 C14 C13 120.6(4) . . ? 
C15 C14 H14 119.7 . . ? 
C13 C14 H14 119.7 . . ? 
C14 C15 C10 120.2(4) . . ? 
C14 C15 H15 119.9 . . ? 
C10 C15 H15 119.9 . . ? 
C21 C20 C25 118.8(3) . . ? 
C21 C20 P1 124.2(3) . . ? 
C25 C20 P1 117.0(2) . . ? 
C20 C21 C22 120.0(3) . . ? 
C20 C21 H21 120.0 . . ? 
C22 C21 H21 120.0 . . ? 
C23 C22 C21 120.6(3) . . ? 
C23 C22 H22 119.7 . . ? 
C21 C22 H22 119.7 . . ? 
C24 C23 C22 119.8(3) . . ? 
C24 C23 H23 120.1 . . ? 
C22 C23 H23 120.1 . . ? 
C23 C24 C25 120.0(3) . . ? 
C23 C24 H24 120.0 . . ? 
C25 C24 H24 120.0 . . ? 
C24 C25 C20 120.9(3) . . ? 
C24 C25 H25 119.6 . . ? 
C20 C25 H25 119.6 . . ? 
C35 C30 C31 119.3(3) . . ? 
C35 C30 P1 116.4(2) . . ? 
C31 C30 P1 124.3(2) . . ? 
C32 C31 C30 120.0(3) . . ? 
C32 C31 H31 120.0 . . ? 
C30 C31 H31 120.0 . . ? 
C33 C32 C31 120.7(3) . . ? 
C33 C32 H32 119.6 . . ? 
C31 C32 H32 119.6 . . ? 
C34 C33 C32 119.4(3) . . ? 
C34 C33 H33 120.3 . . ? 
C32 C33 H33 120.3 . . ? 
C33 C34 C35 120.7(3) . . ? 
C33 C34 H34 119.6 . . ? 
C35 C34 H34 119.6 . . ? 
C30 C35 C34 119.9(3) . . ? 
C30 C35 H35 120.1 . . ? 
C34 C35 H35 120.1 . . ? 
C45 C40 C41 119.1(3) . . ? 
C45 C40 P1 119.7(2) . . ? 
C41 C40 P1 121.0(2) . . ? 
C42 C41 C40 120.7(3) . . ? 
C42 C41 H41 119.6 . . ? 
C40 C41 H41 119.6 . . ? 
C41 C42 C43 119.5(3) . . ? 
C41 C42 H42 120.2 . . ? 
C43 C42 H42 120.2 . . ? 
C44 C43 C42 120.5(3) . . ? 
C44 C43 H43 119.7 . . ? 
C42 C43 H43 119.7 . . ? 
C43 C44 C45 120.0(3) . . ? 
C43 C44 H44 120.0 . . ? 
C45 C44 H44 120.0 . . ? 
C44 C45 C40 120.1(3) . . ? 
C44 C45 H45 120.0 . . ? 
C40 C45 H45 120.0 . . ? 
 
_diffrn_measured_fraction_theta_max    0.949 
_diffrn_reflns_theta_full              26.00 
_diffrn_measured_fraction_theta_full   0.949 
_refine_diff_density_max    1.074 
_refine_diff_density_min   -1.297 
_refine_diff_density_rms    0.102 
