#------------------------------------------------------------------------------
#$Date: 2018-07-11 15:20:40 +0300 (Wed, 11 Jul 2018) $
#$Revision: 208973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/37/7103772.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7103772
loop_
_publ_author_name
'Leca, François'
'Sauthier, Mathieu'
'Le Guennic, Boris'
'Lescop, Christophe'
'Toupet, Loic'
'Halet, Jean-François'
'Réau, Régis'
_publ_section_title
;
 Stereospecific isomerisation of P-heterocycles triggered by coordination:
 synthesis of the first P,N-chelates featuring a 2-phospholene moiety
;
_journal_coden_ASTM              CHCOFS
_journal_name_full
;
 Chemical Communications (Cambridge, United Kingdom)
;
_journal_page_first              1774
_journal_page_last               1775
_journal_paper_doi               10.1039/b304308h
_journal_year                    2003
_chemical_formula_sum            'C23.5 H26 Cl3 N P Pd S'
_chemical_formula_weight         598.23
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 106.722(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.866(5)
_cell_length_b                   15.475(5)
_cell_length_c                   16.973(5)
_cell_measurement_temperature    293(2)
_cell_volume                     2733.3(17)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       none
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0171
_diffrn_reflns_av_sigmaI/netI    0.0286
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            12092
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.92
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    1.118
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1208
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         1.254
_refine_diff_density_min         -0.837
_refine_diff_density_rms         0.132
_refine_ls_extinction_coef       0.0070(13)
_refine_ls_extinction_expression Fc^*^==kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         6251
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0709
_refine_ls_R_factor_gt           0.0570
_refine_ls_shift/su_max          2.106
_refine_ls_shift/su_mean         0.120
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w==1/[σ²(Fo²)+(0.1149P)²+3.1669P] where P==(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1687
_refine_ls_wR_factor_ref         0.1869
_reflns_number_gt                4972
_reflns_number_total             6251
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b304308h.txt
_cod_data_source_block           compound_2c'
_cod_original_sg_symbol_H-M      P21/n
_cod_original_formula_sum        'C23.50 H26 Cl3 N P Pd S'
_cod_database_code               7103772
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'
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 0.75507(3) 0.03964(2) 0.28992(2) 0.04885(17) Uani 1 1 d . . .
Cl1 Cl 0.61412(16) -0.03435(9) 0.34260(12) 0.0811(5) Uani 1 1 d . . .
Cl2 Cl 0.7444(2) -0.06794(12) 0.18811(14) 0.1094(7) Uani 1 1 d . . .
P1 P 0.75702(9) 0.14143(6) 0.37976(6) 0.0410(2) Uani 1 1 d . . .
S1 S 0.65237(14) 0.07311(11) 0.55784(11) 0.0789(4) Uani 1 1 d . . .
N1 N 0.8799(3) 0.1198(2) 0.2518(2) 0.0489(8) Uani 1 1 d . . .
C1 C 0.8737(4) 0.2203(3) 0.3625(3) 0.0467(9) Uani 1 1 d . . .
C2 C 0.9880(4) 0.2122(3) 0.4400(3) 0.0549(10) Uani 1 1 d . . .
C3 C 1.1055(6) 0.2460(5) 0.4497(4) 0.084(2) Uani 1 1 d . . .
C4 C 1.2114(7) 0.2396(7) 0.5258(4) 0.122(4) Uani 1 1 d . . .
H4A H 1.2609 0.2927 0.5340 0.147 Uiso 1 1 calc R . .
H4B H 1.2679 0.1926 0.5211 0.147 Uiso 1 1 calc R . .
C5 C 1.1601(6) 0.2235(6) 0.6012(4) 0.102(3) Uani 1 1 d . . .
H5A H 1.2315 0.2094 0.6488 0.122 Uiso 1 1 calc R . .
H5B H 1.1201 0.2758 0.6135 0.122 Uiso 1 1 calc R . .
C6 C 1.0634(5) 0.1505(5) 0.5849(3) 0.0728(15) Uani 1 1 d . . .
H6A H 1.1077 0.0963 0.5838 0.087 Uiso 1 1 calc R . .
H6B H 1.0245 0.1477 0.6296 0.087 Uiso 1 1 calc R . .
C7 C 0.9594(4) 0.1610(3) 0.5052(3) 0.0511(9) Uani 1 1 d . . .
C8 C 0.8431(4) 0.1223(3) 0.4863(3) 0.0448(8) Uani 1 1 d . . .
C9 C 0.8009(4) 0.0647(3) 0.5407(3) 0.0474(9) Uani 1 1 d . . .
C10 C 0.8720(5) -0.0018(4) 0.5893(4) 0.0709(15) Uani 1 1 d . . .
H10 H 0.9560 -0.0162 0.5915 0.085 Uiso 1 1 calc R . .
C11 C 0.7967(6) -0.0452(4) 0.6358(4) 0.0792(17) Uani 1 1 d . . .
H11 H 0.8265 -0.0924 0.6699 0.095 Uiso 1 1 calc R . .
C12 C 0.6811(6) -0.0108(4) 0.6249(4) 0.0792(16) Uani 1 1 d . . .
H12 H 0.6223 -0.0306 0.6512 0.095 Uiso 1 1 calc R . .
C13 C 0.9099(4) 0.1985(3) 0.2857(2) 0.0457(9) Uani 1 1 d . . .
C14 C 0.9756(5) 0.2591(3) 0.2524(3) 0.0598(11) Uani 1 1 d . . .
H14 H 0.9892 0.3147 0.2739 0.072 Uiso 1 1 calc R . .
C15 C 1.0201(5) 0.2357(5) 0.1874(3) 0.0726(15) Uani 1 1 d . . .
H15 H 1.0652 0.2750 0.1648 0.087 Uiso 1 1 calc R . .
C16 C 0.9969(6) 0.1535(5) 0.1565(3) 0.0800(17) Uani 1 1 d . . .
H16 H 1.0296 0.1356 0.1142 0.096 Uiso 1 1 calc R . .
C17 C 0.9250(5) 0.0976(4) 0.1885(3) 0.0646(12) Uani 1 1 d . . .
H17 H 0.9070 0.0428 0.1657 0.078 Uiso 1 1 calc R . .
C20 C 0.6000(4) 0.1909(3) 0.3699(3) 0.0504(9) Uani 1 1 d . . .
C21 C 0.5369(5) 0.2150(4) 0.2793(3) 0.0655(13) Uani 1 1 d . . .
H21A H 0.5310 0.1641 0.2451 0.079 Uiso 1 1 calc R . .
H21B H 0.5896 0.2574 0.2619 0.079 Uiso 1 1 calc R . .
C22 C 0.4029(6) 0.2520(5) 0.2684(4) 0.091(2) Uani 1 1 d . . .
H22A H 0.3669 0.2703 0.2118 0.109 Uiso 1 1 calc R . .
H22B H 0.3479 0.2071 0.2796 0.109 Uiso 1 1 calc R . .
C23 C 0.4049(7) 0.3271(5) 0.3243(5) 0.103(2) Uani 1 1 d . . .
H23A H 0.4495 0.3750 0.3078 0.124 Uiso 1 1 calc R . .
H23B H 0.3174 0.3453 0.3186 0.124 Uiso 1 1 calc R . .
C24 C 0.4711(7) 0.3051(5) 0.4147(5) 0.098(2) Uani 1 1 d . . .
H24A H 0.4200 0.2629 0.4336 0.117 Uiso 1 1 calc R . .
H24B H 0.4765 0.3568 0.4479 0.117 Uiso 1 1 calc R . .
C25 C 0.6067(5) 0.2688(3) 0.4264(3) 0.0609(12) Uani 1 1 d . . .
H25A H 0.6612 0.3131 0.4135 0.073 Uiso 1 1 calc R . .
H25B H 0.6438 0.2515 0.4832 0.073 Uiso 1 1 calc R . .
Cl70 Cl 1.1020(10) 0.6203(4) 0.4337(5) 0.244(6) Uani 0.50 1 d P . .
Cl72 Cl 1.2868(14) 0.4883(8) 0.4560(9) 0.286(7) Uani 0.50 1 d P . .
C70 C 1.080(2) 0.5125(10) 0.4021(14) 0.127(7) Uani 0.50 1 d P . .
H70A H 1.0514 0.5055 0.3429 0.153 Uiso 0.50 1 calc PR . .
H70B H 1.0264 0.4801 0.4282 0.153 Uiso 0.50 1 calc PR . .
H1 H 0.850(5) 0.284(4) 0.363(3) 0.061(14) Uiso 1 1 d . . .
H3 H 1.108(7) 0.286(5) 0.409(4) 0.10(2) Uiso 1 1 d . . .
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'
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'
Cl Cl 0.1484 0.1585 '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'
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 Pd1 P1 84.89(11) . . ?
N1 Pd1 Cl1 172.60(11) . . ?
P1 Pd1 Cl1 87.78(5) . . ?
N1 Pd1 Cl2 95.25(11) . . ?
P1 Pd1 Cl2 177.35(7) . . ?
Cl1 Pd1 Cl2 92.02(6) . . ?
C8 P1 C20 111.14(19) . . ?
C8 P1 C1 94.93(19) . . ?
C20 P1 C1 111.9(2) . . ?
C8 P1 Pd1 118.57(14) . . ?
C20 P1 Pd1 114.50(15) . . ?
C1 P1 Pd1 103.60(14) . . ?
C12 S1 C9 93.1(3) . . ?
C17 N1 C13 118.2(4) . . ?
C17 N1 Pd1 121.1(4) . . ?
C13 N1 Pd1 120.5(3) . . ?
C13 C1 C2 112.1(3) . . ?
C13 C1 P1 110.6(3) . . ?
C2 C1 P1 103.6(3) . . ?
C3 C2 C7 121.1(5) . . ?
C3 C2 C1 125.5(5) . . ?
C7 C2 C1 113.4(3) . . ?
C2 C3 C4 124.0(6) . . ?
C3 C4 C5 111.1(5) . . ?
C6 C5 C4 111.3(5) . . ?
C7 C6 C5 112.8(5) . . ?
C8 C7 C2 116.6(4) . . ?
C8 C7 C6 125.2(4) . . ?
C2 C7 C6 118.1(4) . . ?
C7 C8 C9 124.5(4) . . ?
C7 C8 P1 110.2(3) . . ?
C9 C8 P1 124.9(3) . . ?
C10 C9 C8 127.1(4) . . ?
C10 C9 S1 109.9(3) . . ?
C8 C9 S1 122.9(3) . . ?
C9 C10 C11 110.9(5) . . ?
C12 C11 C10 113.4(5) . . ?
C11 C12 S1 112.7(4) . . ?
N1 C13 C14 121.7(4) . . ?
N1 C13 C1 118.8(4) . . ?
C14 C13 C1 119.5(4) . . ?
C15 C14 C13 119.2(5) . . ?
C14 C15 C16 118.8(5) . . ?
C15 C16 C17 119.6(5) . . ?
N1 C17 C16 122.1(6) . . ?
C21 C20 C25 111.3(4) . . ?
C21 C20 P1 109.2(3) . . ?
C25 C20 P1 113.4(3) . . ?
C20 C21 C22 110.3(5) . . ?
C23 C22 C21 112.1(5) . . ?
C24 C23 C22 112.3(6) . . ?
C23 C24 C25 111.5(5) . . ?
C20 C25 C24 109.7(5) . . ?
Cl70 C70 Cl72 90.2(11) . . ?
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 N1 2.074(4) . ?
Pd1 P1 2.1883(11) . ?
Pd1 Cl1 2.2902(16) . ?
Pd1 Cl2 2.3782(16) . ?
P1 C8 1.804(4) . ?
P1 C20 1.833(4) . ?
P1 C1 1.843(4) . ?
S1 C12 1.695(7) . ?
S1 C9 1.725(4) . ?
N1 C17 1.346(6) . ?
N1 C13 1.346(6) . ?
C1 C13 1.505(6) . ?
C1 C2 1.532(6) . ?
C2 C3 1.345(7) . ?
C2 C7 1.466(6) . ?
C3 C4 1.465(9) . ?
C4 C5 1.556(9) . ?
C5 C6 1.513(8) . ?
C6 C7 1.501(7) . ?
C7 C8 1.351(6) . ?
C8 C9 1.450(6) . ?
C9 C10 1.404(7) . ?
C10 C11 1.455(8) . ?
C11 C12 1.327(9) . ?
C13 C14 1.393(6) . ?
C14 C15 1.374(8) . ?
C15 C16 1.371(10) . ?
C16 C17 1.378(9) . ?
C20 C21 1.538(6) . ?
C20 C25 1.529(7) . ?
C21 C22 1.525(7) . ?
C22 C23 1.496(11) . ?
C23 C24 1.534(10) . ?
C24 C25 1.536(7) . ?
Cl70 C70 1.746(19) . ?
Cl72 C70 2.20(3) . ?
