 
data_s92
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C23 H18 I2 N O3 P W'
_chemical_formula_sum
 'C23 H18 I2 N O3 P W'
_chemical_formula_weight          825.00
 
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'
 'N'  'N'   0.0061   0.0033
 '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'
 'I'  'I'  -0.4742   1.8119
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'W'  'W'  -0.8490   6.8722
 '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)/n
_symmetry_space_group_name_hall   '-P 2yn'
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x-1/2, -y-1/2, z-1/2'
 
_cell_length_a                    11.456(7)
_cell_length_b                    10.938(2)
_cell_length_c                    20.2783(16)
_cell_angle_alpha                 90.00
_cell_angle_beta                  104.50(2)
_cell_angle_gamma                 90.00
_cell_volume                      2460.1(16)
_cell_formula_units_Z             4
_cell_measurement_temperature     293(2)
_cell_measurement_reflns_used     ?
_cell_measurement_theta_min       ?
_cell_measurement_theta_max       ?
 
_exptl_crystal_description        unk
_exptl_crystal_colour             unk
_exptl_crystal_size_max           0.2
_exptl_crystal_size_mid           0.2
_exptl_crystal_size_min           0.2
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     2.227
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              1528
_exptl_absorpt_coefficient_mu     7.294
_exptl_absorpt_correction_type    none
_exptl_absorpt_correction_T_min   ?
_exptl_absorpt_correction_T_max   ?
_exptl_absorpt_process_details    ?
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       293(2)
_diffrn_radiation_wavelength      0.71069
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source         'rotating anode generator'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Delft instruments FAST area detector'
_diffrn_measurement_method
 'Intensity measurements as described by Darr, Drake, Hursthouse & Malik (1993)'
_diffrn_standards_number         'None'
_diffrn_standards_interval_count 'N/A'
_diffrn_standards_interval_time  'N/A'
_diffrn_standards_decay_%        'N/A'
_diffrn_reflns_number             7089
_diffrn_reflns_av_R_equivalents   0.0639
_diffrn_reflns_av_sigmaI/netI     0.1318
_diffrn_reflns_limit_h_min        -9
_diffrn_reflns_limit_h_max        12
_diffrn_reflns_limit_k_min        -4
_diffrn_reflns_limit_k_max        12
_diffrn_reflns_limit_l_min        -22
_diffrn_reflns_limit_l_max        22
_diffrn_reflns_theta_min          2.98
_diffrn_reflns_theta_max          24.91
_reflns_number_total              3763
_reflns_number_gt                 3276
_reflns_threshold_expression      >2σ(I)
 
_computing_data_collection        'MADNES (Pflugrath & Messerschmidt, 1989)'
_computing_cell_refinement        REFINE
_computing_data_reduction         'ABSURD (Karaulov, 1992)'
_computing_structure_solution     'SIR92 (Altomare, Cascarano, Giacovazzo & Guaglitardi, 1993)'
_computing_structure_refinement   'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material   SHELXL97
 
_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 > 2σ(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)+(0.0000P)²+0.0000P] 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          3763
_refine_ls_number_parameters      274
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0449
_refine_ls_R_factor_gt            0.0404
_refine_ls_wR_factor_ref          0.1114
_refine_ls_wR_factor_gt           0.1064
_refine_ls_goodness_of_fit_ref    0.735
_refine_ls_restrained_S_all       0.735
_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
W1 W 0.15789(3) 0.24878(3) 0.127997(17) 0.01220(15) Uani 1 1 d . . .
I1 I 0.03750(5) 0.16762(6) 0.22761(3) 0.02368(19) Uani 1 1 d . . .
I2 I 0.28738(5) 0.02354(5) 0.14532(3) 0.02144(18) Uani 1 1 d . . .
P1 P 0.3230(2) 0.3175(2) 0.07095(11) 0.0139(5) Uani 1 1 d . . .
N1 N 0.2985(6) 0.3059(7) 0.2157(4) 0.0180(17) Uani 1 1 d . . .
O1 O 0.0353(5) 0.3596(6) -0.0137(3) 0.0258(16) Uani 1 1 d . . .
O2 O 0.0177(6) 0.4834(6) 0.1558(4) 0.0328(17) Uani 1 1 d . . .
O3 O -0.0380(6) 0.0618(6) 0.0539(3) 0.0286(16) Uani 1 1 d . . .
C1 C 0.0826(8) 0.3201(9) 0.0380(5) 0.0202(15) Uani 1 1 d . . .
C2 C 0.0699(8) 0.3984(9) 0.1473(4) 0.022(2) Uani 1 1 d . . .
C3 C 0.0323(8) 0.1309(9) 0.0793(5) 0.0202(15) Uani 1 1 d . . .
C4 C 0.3751(8) 0.3110(8) 0.2643(5) 0.018(2) Uani 1 1 d . . .
C5 C 0.4764(9) 0.3111(10) 0.3230(5) 0.029(2) Uani 1 1 d . . .
H5A H 0.4971 0.2284 0.3371 0.044 Uiso 1 1 calc R . .
H5B H 0.4557 0.3552 0.3594 0.044 Uiso 1 1 calc R . .
H5C H 0.5440 0.3498 0.3116 0.044 Uiso 1 1 calc R . .
C7 C 0.3398(9) 0.2344(8) -0.0040(5) 0.016(2) Uani 1 1 d . . .
C8 C 0.2588(8) 0.1436(8) -0.0327(4) 0.0160(19) Uani 1 1 d . . .
H8 H 0.1946 0.1254 -0.0140 0.019 Uiso 1 1 calc R . .
C9 C 0.2731(9) 0.0796(9) -0.0894(4) 0.025(2) Uani 1 1 d . . .
H9 H 0.2201 0.0171 -0.1082 0.030 Uiso 1 1 calc R . .
C10 C 0.3681(8) 0.1106(9) -0.1175(4) 0.022(2) Uani 1 1 d . . .
H10 H 0.3780 0.0683 -0.1555 0.026 Uiso 1 1 calc R . .
C11 C 0.4469(9) 0.2016(10) -0.0906(5) 0.026(2) Uani 1 1 d . . .
H11 H 0.5088 0.2227 -0.1107 0.031 Uiso 1 1 calc R . .
C12 C 0.4335(9) 0.2624(8) -0.0328(5) 0.020(2) Uani 1 1 d . . .
H12 H 0.4884 0.3229 -0.0133 0.025 Uiso 1 1 calc R . .
C13 C 0.4791(8) 0.3220(8) 0.1236(4) 0.0161(19) Uani 1 1 d . . .
C14 C 0.5447(8) 0.2136(10) 0.1367(5) 0.024(2) Uani 1 1 d . . .
H14 H 0.5106 0.1416 0.1162 0.029 Uiso 1 1 calc R . .
C15 C 0.6585(9) 0.2110(10) 0.1792(5) 0.030(2) Uani 1 1 d . . .
H15 H 0.7001 0.1375 0.1883 0.036 Uiso 1 1 calc R . .
C16 C 0.7111(9) 0.3185(11) 0.2085(5) 0.035(3) Uani 1 1 d . . .
H16 H 0.7880 0.3175 0.2376 0.042 Uiso 1 1 calc R . .
C17 C 0.6492(9) 0.4265(11) 0.1942(5) 0.037(3) Uani 1 1 d . . .
H17 H 0.6849 0.4991 0.2130 0.045 Uiso 1 1 calc R . .
C18 C 0.5349(8) 0.4280(10) 0.1525(5) 0.027(2) Uani 1 1 d . . .
H18 H 0.4940 0.5020 0.1434 0.033 Uiso 1 1 calc R . .
C19 C 0.2923(7) 0.4766(8) 0.0448(4) 0.0156(19) Uani 1 1 d . . .
C20 C 0.2756(8) 0.5175(9) -0.0229(5) 0.026(2) Uani 1 1 d . . .
H20 H 0.2815 0.4631 -0.0571 0.031 Uiso 1 1 calc R . .
C21 C 0.2510(8) 0.6369(10) -0.0374(5) 0.031(3) Uani 1 1 d . . .
H21 H 0.2395 0.6630 -0.0823 0.037 Uiso 1 1 calc R . .
C22 C 0.2424(9) 0.7210(10) 0.0115(6) 0.033(3) Uani 1 1 d . . .
H22 H 0.2274 0.8030 0.0003 0.039 Uiso 1 1 calc R . .
C23 C 0.2564(8) 0.6813(9) 0.0773(6) 0.027(2) Uani 1 1 d . . .
H23 H 0.2500 0.7370 0.1109 0.032 Uiso 1 1 calc R . .
C24 C 0.2801(8) 0.5589(9) 0.0945(5) 0.022(2) Uani 1 1 d . . .
H24 H 0.2877 0.5327 0.1390 0.026 Uiso 1 1 calc R . .
 
 
_geom_special_details
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
W1 C1 1.974(9) . ?
W1 C3 1.999(9) . ?
W1 C2 2.011(10) . ?
W1 N1 2.170(7) . ?
W1 P1 2.564(3) . ?
W1 I2 2.8519(9) . ?
W1 I1 2.8576(10) . ?
P1 C7 1.823(9) . ?
P1 C19 1.827(9) . ?
P1 C13 1.840(9) . ?
N1 C4 1.146(11) . ?
O1 C1 1.138(10) . ?
O2 C2 1.142(11) . ?
O3 C3 1.130(11) . ?
C4 C5 1.439(13) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C7 C12 1.378(14) . ?
C7 C8 1.383(12) . ?
C8 C9 1.390(13) . ?
C8 H8 0.9300 . ?
C9 C10 1.391(13) . ?
C9 H9 0.9300 . ?
C10 C11 1.363(14) . ?
C10 H10 0.9300 . ?
C11 C12 1.389(13) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C18 1.381(13) . ?
C13 C14 1.393(13) . ?
C14 C15 1.371(13) . ?
C14 H14 0.9300 . ?
C15 C16 1.386(15) . ?
C15 H15 0.9300 . ?
C16 C17 1.371(15) . ?
C16 H16 0.9300 . ?
C17 C18 1.369(13) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C24 1.385(13) . ?
C19 C20 1.410(13) . ?
C20 C21 1.353(14) . ?
C20 H20 0.9300 . ?
C21 C22 1.375(16) . ?
C21 H21 0.9300 . ?
C22 C23 1.374(15) . ?
C22 H22 0.9300 . ?
C23 C24 1.393(13) . ?
C23 H23 0.9300 . ?
C24 H24 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
C1 W1 C3 72.8(4) . . ?
C1 W1 C2 74.6(4) . . ?
C3 W1 C2 106.7(4) . . ?
C1 W1 N1 134.9(3) . . ?
C3 W1 N1 152.2(3) . . ?
C2 W1 N1 84.9(3) . . ?
C1 W1 P1 70.6(3) . . ?
C3 W1 P1 119.2(3) . . ?
C2 W1 P1 108.1(3) . . ?
N1 W1 P1 78.8(2) . . ?
C1 W1 I2 123.3(3) . . ?
C3 W1 I2 78.0(3) . . ?
C2 W1 I2 161.7(3) . . ?
N1 W1 I2 83.8(2) . . ?
P1 W1 I2 83.64(6) . . ?
C1 W1 I1 126.9(3) . . ?
C3 W1 I1 74.5(3) . . ?
C2 W1 I1 76.2(3) . . ?
N1 W1 I1 84.32(19) . . ?
P1 W1 I1 161.99(5) . . ?
I2 W1 I1 88.44(3) . . ?
C7 P1 C19 106.6(4) . . ?
C7 P1 C13 101.9(4) . . ?
C19 P1 C13 103.4(4) . . ?
C7 P1 W1 118.3(3) . . ?
C19 P1 W1 107.5(3) . . ?
C13 P1 W1 117.7(3) . . ?
C4 N1 W1 166.0(7) . . ?
O1 C1 W1 177.6(8) . . ?
O2 C2 W1 177.5(8) . . ?
O3 C3 W1 177.5(8) . . ?
N1 C4 C5 175.7(10) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C12 C7 C8 119.5(9) . . ?
C12 C7 P1 119.9(7) . . ?
C8 C7 P1 120.6(7) . . ?
C7 C8 C9 120.2(9) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C8 C9 C10 118.9(9) . . ?
C8 C9 H9 120.6 . . ?
C10 C9 H9 120.6 . . ?
C11 C10 C9 121.5(9) . . ?
C11 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C10 C11 C12 119.0(9) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 H11 120.5 . . ?
C7 C12 C11 120.9(9) . . ?
C7 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C18 C13 C14 117.6(9) . . ?
C18 C13 P1 123.2(7) . . ?
C14 C13 P1 119.2(7) . . ?
C15 C14 C13 121.3(10) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C14 C15 C16 119.7(10) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C17 C16 C15 119.6(10) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C18 C17 C16 120.3(10) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C13 121.4(10) . . ?
C17 C18 H18 119.3 . . ?
C13 C18 H18 119.3 . . ?
C24 C19 C20 119.2(9) . . ?
C24 C19 P1 117.1(7) . . ?
C20 C19 P1 123.7(7) . . ?
C21 C20 C19 119.3(10) . . ?
C21 C20 H20 120.3 . . ?
C19 C20 H20 120.3 . . ?
C20 C21 C22 122.5(10) . . ?
C20 C21 H21 118.8 . . ?
C22 C21 H21 118.8 . . ?
C23 C22 C21 118.5(10) . . ?
C23 C22 H22 120.8 . . ?
C21 C22 H22 120.8 . . ?
C22 C23 C24 121.0(10) . . ?
C22 C23 H23 119.5 . . ?
C24 C23 H23 119.5 . . ?
C19 C24 C23 119.5(9) . . ?
C19 C24 H24 120.3 . . ?
C23 C24 H24 120.3 . . ?
 
_diffrn_measured_fraction_theta_max    0.877
_diffrn_reflns_theta_full              24.91
_diffrn_measured_fraction_theta_full   0.877
_refine_diff_density_max    1.447
_refine_diff_density_min   -2.190
_refine_diff_density_rms    0.268
