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#$Date: 2019-03-05 10:52:05 +0200 (Tue, 05 Mar 2019) $
#$Revision: 213973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/37/7103768.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_7103768
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 H26 Cl2 N P Pd S'
_chemical_formula_weight         556.78
_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                 106.6950(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.3320(2)
_cell_length_b                   17.1370(5)
_cell_length_c                   13.1100(4)
_cell_measurement_temperature    293(2)
_cell_volume                     2223.40(10)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0512
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5046
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         2.01
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    1.252
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.663
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1128
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.916
_refine_diff_density_min         -1.185
_refine_diff_density_rms         0.128
_refine_ls_extinction_coef       0.0012(3)
_refine_ls_extinction_expression Fc^*^==kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         5046
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0662
_refine_ls_R_factor_gt           0.0444
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w==1/[σ²(Fo²)+(0.0415P)²+6.2387P] where P==(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1039
_refine_ls_wR_factor_ref         0.1142
_reflns_number_gt                3887
_reflns_number_total             5046
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b304308h.txt
_cod_data_source_block           compound_1c'
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               7103768
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
C1 C 0.1840(4) 0.1115(3) 0.7001(4) 0.0235(9) Uani 1 1 d . . .
C2 C 0.1004(5) 0.1244(3) 0.6011(4) 0.0246(9) Uani 1 1 d . . .
C3 C 0.1405(5) 0.1650(3) 0.5131(4) 0.0291(10) Uani 1 1 d . . .
H3A H 0.2273 0.1451 0.5102 0.035 Uiso 1 1 calc R . .
H3B H 0.1505 0.2204 0.5284 0.035 Uiso 1 1 calc R . .
C4 C 0.0363(5) 0.1529(3) 0.4050(4) 0.0355(12) Uani 1 1 d . . .
H4A H 0.0559 0.1876 0.3529 0.043 Uiso 1 1 calc R . .
H4B H 0.0413 0.0996 0.3814 0.043 Uiso 1 1 calc R . .
C5 C -0.1044(5) 0.1691(3) 0.4132(4) 0.0357(12) Uani 1 1 d . . .
H5A H -0.1683 0.1694 0.3426 0.043 Uiso 1 1 calc R . .
H5B H -0.1066 0.2200 0.4450 0.043 Uiso 1 1 calc R . .
C6 C -0.1439(5) 0.1064(3) 0.4814(4) 0.0306(11) Uani 1 1 d . . .
H6A H -0.2268 0.1220 0.4964 0.037 Uiso 1 1 calc R . .
H6B H -0.1617 0.0580 0.4413 0.037 Uiso 1 1 calc R . .
C7 C -0.0370(4) 0.0919(3) 0.5850(3) 0.0241(9) Uani 1 1 d . . .
C8 C -0.0547(4) 0.0493(3) 0.6683(3) 0.0207(9) Uani 1 1 d . . .
C9 C -0.1744(4) 0.0121(3) 0.6819(4) 0.0231(9) Uani 1 1 d . . .
C10 C -0.1804(4) -0.0311(3) 0.7688(4) 0.0241(9) Uani 1 1 d . . .
H10 H -0.1069 -0.0384 0.8286 0.029 Uiso 1 1 calc R . .
C11 C -0.3105(4) -0.0634(3) 0.7580(4) 0.0273(10) Uani 1 1 d . . .
H11 H -0.3311 -0.0943 0.8095 0.033 Uiso 1 1 calc R . .
C12 C -0.4008(5) -0.0441(3) 0.6644(4) 0.0332(11) Uani 1 1 d . . .
H12 H -0.4906 -0.0600 0.6444 0.040 Uiso 1 1 calc R . .
C13 C 0.3310(4) 0.1155(3) 0.7422(4) 0.0252(9) Uani 1 1 d . . .
C14 C 0.4124(5) 0.1728(3) 0.7178(4) 0.0307(11) Uani 1 1 d . . .
H14 H 0.3747 0.2120 0.6693 0.037 Uiso 1 1 calc R . .
C15 C 0.5506(5) 0.1709(3) 0.7665(4) 0.0305(11) Uani 1 1 d . . .
H15 H 0.6066 0.2078 0.7489 0.037 Uiso 1 1 calc R . .
C16 C 0.6046(5) 0.1143(3) 0.8410(4) 0.0308(11) Uani 1 1 d . . .
H16 H 0.6964 0.1139 0.8771 0.037 Uiso 1 1 calc R . .
C17 C 0.5188(4) 0.0574(3) 0.8613(4) 0.0261(9) Uani 1 1 d . . .
H17 H 0.5554 0.0185 0.9105 0.031 Uiso 1 1 calc R . .
C20 C 0.0544(4) 0.1225(2) 0.8747(3) 0.0199(8) Uani 1 1 d . . .
H20 H 0.0097 0.0913 0.9175 0.024 Uiso 1 1 calc R . .
C21 C -0.0448(4) 0.1864(3) 0.8174(4) 0.0234(9) Uani 1 1 d . . .
H21A H -0.0058 0.2151 0.7696 0.028 Uiso 1 1 calc R . .
H21B H -0.1280 0.1625 0.7752 0.028 Uiso 1 1 calc R . .
C22 C -0.0757(4) 0.2428(3) 0.8980(4) 0.0242(9) Uani 1 1 d . . .
H22A H -0.1337 0.2844 0.8603 0.029 Uiso 1 1 calc R . .
H22B H -0.1233 0.2152 0.9408 0.029 Uiso 1 1 calc R . .
C23 C 0.0543(4) 0.2777(3) 0.9702(4) 0.0275(10) Uani 1 1 d . . .
H23A H 0.0325 0.3118 1.0219 0.033 Uiso 1 1 calc R . .
H23B H 0.0979 0.3088 0.9278 0.033 Uiso 1 1 calc R . .
C24 C 0.1513(4) 0.2143(3) 1.0284(4) 0.0270(10) Uani 1 1 d . . .
H24A H 0.1110 0.1862 1.0759 0.032 Uiso 1 1 calc R . .
H24B H 0.2342 0.2383 1.0712 0.032 Uiso 1 1 calc R . .
C25 C 0.1841(4) 0.1569(3) 0.9497(4) 0.0252(9) Uani 1 1 d . . .
H25A H 0.2401 0.1150 0.9887 0.030 Uiso 1 1 calc R . .
H25B H 0.2345 0.1836 0.9081 0.030 Uiso 1 1 calc R . .
N1 N 0.3867(3) 0.0566(2) 0.8130(3) 0.0230(8) Uani 1 1 d . . .
P1 P 0.09932(10) 0.05669(7) 0.77832(9) 0.0198(2) Uani 1 1 d . . .
S1 S -0.33163(12) 0.01239(8) 0.58711(10) 0.0321(3) Uani 1 1 d . . .
Cl1 Cl 0.12181(9) -0.12014(6) 0.88368(8) 0.0226(2) Uani 1 1 d . . .
Cl2 Cl 0.43955(10) -0.12465(7) 0.88256(10) 0.0283(3) Uani 1 1 d . . .
Pd1 Pd 0.26254(3) -0.031491(19) 0.83986(3) 0.02033(12) Uani 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
C2 C1 C13 131.5(4) . . ?
C2 C1 P1 110.6(3) . . ?
C13 C1 P1 115.7(3) . . ?
C1 C2 C7 113.4(4) . . ?
C1 C2 C3 124.8(4) . . ?
C7 C2 C3 121.9(4) . . ?
C2 C3 C4 111.9(4) . . ?
C5 C4 C3 110.2(4) . . ?
C4 C5 C6 109.6(4) . . ?
C7 C6 C5 113.2(4) . . ?
C8 C7 C2 115.4(4) . . ?
C8 C7 C6 125.2(4) . . ?
C2 C7 C6 119.4(4) . . ?
C7 C8 C9 130.4(4) . . ?
C7 C8 P1 108.0(3) . . ?
C9 C8 P1 121.1(3) . . ?
C10 C9 C8 125.7(4) . . ?
C10 C9 S1 109.8(3) . . ?
C8 C9 S1 124.5(3) . . ?
C9 C10 C11 113.1(4) . . ?
C12 C11 C10 112.4(4) . . ?
C11 C12 S1 112.4(4) . . ?
N1 C13 C14 120.6(4) . . ?
N1 C13 C1 114.0(4) . . ?
C14 C13 C1 125.4(4) . . ?
C15 C14 C13 119.3(5) . . ?
C16 C15 C14 119.8(4) . . ?
C15 C16 C17 118.5(4) . . ?
N1 C17 C16 122.7(5) . . ?
C25 C20 C21 112.1(4) . . ?
C25 C20 P1 109.1(3) . . ?
C21 C20 P1 111.3(3) . . ?
C22 C21 C20 110.7(4) . . ?
C23 C22 C21 110.8(4) . . ?
C22 C23 C24 111.5(4) . . ?
C23 C24 C25 111.1(4) . . ?
C24 C25 C20 110.9(3) . . ?
C17 N1 C13 119.0(4) . . ?
C17 N1 Pd1 121.8(3) . . ?
C13 N1 Pd1 119.2(3) . . ?
C1 P1 C8 92.4(2) . . ?
C1 P1 C20 109.3(2) . . ?
C8 P1 C20 104.44(19) . . ?
C1 P1 Pd1 96.84(14) . . ?
C8 P1 Pd1 129.56(15) . . ?
C20 P1 Pd1 118.50(14) . . ?
C12 S1 C9 92.2(2) . . ?
N1 Pd1 P1 83.46(10) . . ?
N1 Pd1 Cl1 173.77(11) . . ?
P1 Pd1 Cl1 94.10(4) . . ?
N1 Pd1 Cl2 93.29(10) . . ?
P1 Pd1 Cl2 172.50(4) . . ?
Cl1 Pd1 Cl2 89.79(4) . . ?
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
C1 C2 1.354(6) . ?
C1 C13 1.461(6) . ?
C1 P1 1.794(4) . ?
C2 C7 1.483(6) . ?
C2 C3 1.504(6) . ?
C3 C4 1.527(7) . ?
C4 C5 1.513(7) . ?
C5 C6 1.528(7) . ?
C6 C7 1.505(6) . ?
C7 C8 1.369(6) . ?
C8 C9 1.448(6) . ?
C8 P1 1.819(4) . ?
C9 C10 1.374(6) . ?
C9 S1 1.739(4) . ?
C10 C11 1.423(6) . ?
C11 C12 1.352(7) . ?
C12 S1 1.700(5) . ?
C13 N1 1.381(6) . ?
C13 C14 1.389(6) . ?
C14 C15 1.387(7) . ?
C15 C16 1.377(7) . ?
C16 C17 1.393(6) . ?
C17 N1 1.329(5) . ?
C20 C25 1.534(6) . ?
C20 C21 1.540(6) . ?
C20 P1 1.849(4) . ?
C21 C22 1.531(6) . ?
C22 C23 1.525(6) . ?
C23 C24 1.525(7) . ?
C24 C25 1.533(6) . ?
N1 Pd1 2.076(4) . ?
P1 Pd1 2.2353(11) . ?
Cl1 Pd1 2.2874(10) . ?
Cl2 Pd1 2.3704(11) . ?
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
C13 C1 C2 C7 163.0(5) . . . . ?
P1 C1 C2 C7 1.3(5) . . . . ?
C13 C1 C2 C3 -15.0(8) . . . . ?
P1 C1 C2 C3 -176.8(4) . . . . ?
C1 C2 C3 C4 166.0(4) . . . . ?
C7 C2 C3 C4 -11.9(6) . . . . ?
C2 C3 C4 C5 48.3(6) . . . . ?
C3 C4 C5 C6 -68.3(6) . . . . ?
C4 C5 C6 C7 48.9(6) . . . . ?
C1 C2 C7 C8 -4.9(6) . . . . ?
C3 C2 C7 C8 173.2(4) . . . . ?
C1 C2 C7 C6 175.9(4) . . . . ?
C3 C2 C7 C6 -6.0(6) . . . . ?
C5 C6 C7 C8 168.1(4) . . . . ?
C5 C6 C7 C2 -12.8(6) . . . . ?
C2 C7 C8 C9 177.5(4) . . . . ?
C6 C7 C8 C9 -3.4(8) . . . . ?
C2 C7 C8 P1 5.8(5) . . . . ?
C6 C7 C8 P1 -175.0(4) . . . . ?
C7 C8 C9 C10 178.6(5) . . . . ?
P1 C8 C9 C10 -10.7(6) . . . . ?
C7 C8 C9 S1 1.2(7) . . . . ?
P1 C8 C9 S1 171.9(2) . . . . ?
C8 C9 C10 C11 -177.5(4) . . . . ?
S1 C9 C10 C11 0.2(5) . . . . ?
C9 C10 C11 C12 -0.4(6) . . . . ?
C10 C11 C12 S1 0.4(6) . . . . ?
C2 C1 C13 N1 -139.7(5) . . . . ?
P1 C1 C13 N1 21.3(5) . . . . ?
C2 C1 C13 C14 41.5(8) . . . . ?
P1 C1 C13 C14 -157.5(4) . . . . ?
N1 C13 C14 C15 -0.9(7) . . . . ?
C1 C13 C14 C15 177.8(4) . . . . ?
C13 C14 C15 C16 -2.4(7) . . . . ?
C14 C15 C16 C17 3.4(7) . . . . ?
C15 C16 C17 N1 -1.3(7) . . . . ?
C25 C20 C21 C22 -54.7(4) . . . . ?
P1 C20 C21 C22 -177.2(3) . . . . ?
C20 C21 C22 C23 55.7(5) . . . . ?
C21 C22 C23 C24 -57.2(5) . . . . ?
C22 C23 C24 C25 56.7(5) . . . . ?
C23 C24 C25 C20 -54.7(5) . . . . ?
C21 C20 C25 C24 54.2(5) . . . . ?
P1 C20 C25 C24 177.9(3) . . . . ?
C16 C17 N1 C13 -1.9(7) . . . . ?
C16 C17 N1 Pd1 177.3(3) . . . . ?
C14 C13 N1 C17 3.0(7) . . . . ?
C1 C13 N1 C17 -175.9(4) . . . . ?
C14 C13 N1 Pd1 -176.2(3) . . . . ?
C1 C13 N1 Pd1 4.9(5) . . . . ?
C2 C1 P1 C8 1.6(4) . . . . ?
C13 C1 P1 C8 -163.3(4) . . . . ?
C2 C1 P1 C20 -104.6(3) . . . . ?
C13 C1 P1 C20 90.5(4) . . . . ?
C2 C1 P1 Pd1 132.0(3) . . . . ?
C13 C1 P1 Pd1 -32.9(3) . . . . ?
C7 C8 P1 C1 -4.2(3) . . . . ?
C9 C8 P1 C1 -176.8(4) . . . . ?
C7 C8 P1 C20 106.4(3) . . . . ?
C9 C8 P1 C20 -66.2(4) . . . . ?
C7 C8 P1 Pd1 -105.2(3) . . . . ?
C9 C8 P1 Pd1 82.2(4) . . . . ?
C25 C20 P1 C1 -61.7(3) . . . . ?
C21 C20 P1 C1 62.5(3) . . . . ?
C25 C20 P1 C8 -159.5(3) . . . . ?
C21 C20 P1 C8 -35.4(3) . . . . ?
C25 C20 P1 Pd1 47.8(3) . . . . ?
C21 C20 P1 Pd1 172.0(2) . . . . ?
C11 C12 S1 C9 -0.3(4) . . . . ?
C10 C9 S1 C12 0.0(4) . . . . ?
C8 C9 S1 C12 177.7(4) . . . . ?
C17 N1 Pd1 P1 159.3(3) . . . . ?
C13 N1 Pd1 P1 -21.5(3) . . . . ?
C17 N1 Pd1 Cl1 92.0(10) . . . . ?
C13 N1 Pd1 Cl1 -88.8(10) . . . . ?
C17 N1 Pd1 Cl2 -27.5(3) . . . . ?
C13 N1 Pd1 Cl2 151.7(3) . . . . ?
C1 P1 Pd1 N1 25.37(19) . . . . ?
C8 P1 Pd1 N1 124.2(2) . . . . ?
C20 P1 Pd1 N1 -91.01(18) . . . . ?
C1 P1 Pd1 Cl1 -160.39(15) . . . . ?
C8 P1 Pd1 Cl1 -61.51(18) . . . . ?
C20 P1 Pd1 Cl1 83.24(15) . . . . ?
C1 P1 Pd1 Cl2 -39.2(4) . . . . ?
C8 P1 Pd1 Cl2 59.6(4) . . . . ?
C20 P1 Pd1 Cl2 -155.6(3) . . . . ?
