#------------------------------------------------------------------------------
#$Date: 2016-03-25 13:21:28 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179839 $
#$URL: svn://www.crystallography.net/cod/cif/7/01/35/7013551.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_7013551
loop_
_publ_author_name
'Burrows, Andrew D.'
'Mahon, Mary F.'
'Varrone, Maurizio'
_publ_section_title
;
 The synthesis and late transition metal chemistry of 7-aza-N-indolyl
 phosphines and the activity of their palladium complexes in CO?ethene
 co-polymerisation
;
_journal_issue                   24
_journal_name_full               'Dalton Transactions'
_journal_page_first              4718
_journal_paper_doi               10.1039/b309882f
_journal_year                    2003
_chemical_formula_sum            'C24 H22 F3 N2 O4 P Pd S'
_chemical_formula_weight         628.87
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                71.4250(9)
_cell_angle_beta                 77.4640(8)
_cell_angle_gamma                89.6770(13)
_cell_formula_units_Z            2
_cell_length_a                   8.29100(10)
_cell_length_b                   11.8690(2)
_cell_length_c                   13.8810(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      18
_cell_measurement_theta_min      12
_cell_volume                     1260.97(4)
_computing_data_reduction
'Denzo and Scalepack (otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEX (P.McArdle, 1995)'
_computing_publication_material  'SHELXL-97/2 (Sheldrick,1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       KappaCCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0529
_diffrn_reflns_av_sigmaI/netI    0.0413
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            20472
_diffrn_reflns_theta_full        24.98
_diffrn_reflns_theta_max         24.98
_diffrn_reflns_theta_min         3.58
_exptl_absorpt_coefficient_mu    0.938
_exptl_absorpt_correction_T_max  0.9546
_exptl_absorpt_correction_T_min  0.8721
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sortav Blessing (1995) '
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.656
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.601
_refine_diff_density_min         -0.720
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       0.0028(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.801
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         4408
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.801
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0348
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0857P)²+1.6646P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0969
_refine_ls_wR_factor_ref         0.1052
_reflns_number_gt                3794
_reflns_number_total             4408
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b309882f.txt
_cod_data_source_block           compound8a_k01adb2
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'multiscan' changed to
'multi-scan' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7013551
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.04611(3) 0.50151(2) 0.15028(2) 0.03339(13) Uani 1 1 d . . .
S1 S 0.30719(15) 0.81816(10) 0.25740(9) 0.0566(3) Uani 1 1 d . . .
P1 P 0.06811(11) 0.31209(8) 0.22506(8) 0.0388(2) Uani 1 1 d . . .
F1 F 0.3813(5) 0.7703(8) 0.4364(3) 0.207(4) Uani 1 1 d . . .
F2 F 0.1682(4) 0.6692(4) 0.4385(3) 0.1146(14) Uani 1 1 d . . .
F3 F 0.4104(5) 0.6276(5) 0.3709(4) 0.160(2) Uani 1 1 d . . .
O1 O 0.0077(3) 0.6825(2) 0.0848(2) 0.0397(6) Uani 1 1 d . . .
O2 O 0.2397(4) 0.7475(4) 0.2099(3) 0.0768(10) Uani 1 1 d . . .
O3 O 0.4767(5) 0.8582(4) 0.2096(3) 0.1020(16) Uani 1 1 d . . .
O4 O 0.1994(7) 0.9046(4) 0.2826(4) 0.125(2) Uani 1 1 d . . .
N1 N 0.2095(4) 0.2806(3) 0.1285(3) 0.0447(8) Uani 1 1 d . . .
N2 N 0.2282(3) 0.4840(3) 0.0218(2) 0.0366(7) Uani 1 1 d . . .
C1 C 0.2916(5) 0.1792(4) 0.1169(4) 0.0577(11) Uani 1 1 d . . .
H1 H 0.2721 0.1018 0.1673 0.069 Uiso 1 1 calc R . .
C2 C 0.4002(5) 0.2078(4) 0.0251(4) 0.0558(11) Uani 1 1 d . . .
H2 H 0.4695 0.1547 -0.0003 0.067 Uiso 1 1 calc R . .
C3 C 0.3948(4) 0.3320(4) -0.0287(3) 0.0465(10) Uani 1 1 d . . .
C4 C 0.4765(4) 0.4169(4) -0.1219(3) 0.0491(10) Uani 1 1 d . . .
H4 H 0.5596 0.3958 -0.1709 0.059 Uiso 1 1 calc R . .
C5 C 0.4318(5) 0.5330(4) -0.1402(3) 0.0473(9) Uani 1 1 d . . .
H5 H 0.4858 0.5930 -0.2027 0.057 Uiso 1 1 calc R . .
C6 C 0.3097(4) 0.5634(4) -0.0689(3) 0.0420(9) Uani 1 1 d . . .
H6 H 0.2823 0.6441 -0.0848 0.050 Uiso 1 1 calc R . .
C7 C 0.2747(4) 0.3731(3) 0.0379(3) 0.0380(8) Uani 1 1 d . . .
C8 C -0.1126(4) 0.2131(3) 0.2514(3) 0.0441(9) Uani 1 1 d . . .
C9 C -0.1406(5) 0.1584(4) 0.1809(4) 0.0537(11) Uani 1 1 d . . .
H9 H -0.0584 0.1654 0.1194 0.064 Uiso 1 1 calc R . .
C10 C -0.2896(5) 0.0939(4) 0.2014(5) 0.0659(14) Uani 1 1 d . . .
H10 H -0.3084 0.0549 0.1544 0.079 Uiso 1 1 calc R . .
C11 C -0.4108(5) 0.0853(4) 0.2888(5) 0.0640(14) Uani 1 1 d . . .
H11 H -0.5128 0.0412 0.3013 0.077 Uiso 1 1 calc R . .
C12 C -0.3856(5) 0.1403(4) 0.3587(4) 0.0595(12) Uani 1 1 d . . .
H12 H -0.4697 0.1344 0.4190 0.071 Uiso 1 1 calc R . .
C13 C -0.2357(5) 0.2044(4) 0.3398(4) 0.0516(10) Uani 1 1 d . . .
H13 H -0.2173 0.2425 0.3876 0.062 Uiso 1 1 calc R . .
C14 C 0.1445(4) 0.2647(3) 0.3435(3) 0.0448(9) Uani 1 1 d . . .
C15 C 0.2035(4) 0.3516(4) 0.3779(3) 0.0449(9) Uani 1 1 d . . .
H15 H 0.2088 0.4334 0.3374 0.054 Uiso 1 1 calc R . .
C16 C 0.2546(5) 0.3183(4) 0.4719(3) 0.0555(11) Uani 1 1 d . . .
H16 H 0.2962 0.3769 0.4952 0.067 Uiso 1 1 calc R . .
C17 C 0.2441(5) 0.1994(5) 0.5306(4) 0.0710(15) Uani 1 1 d . . .
H17 H 0.2771 0.1764 0.5952 0.085 Uiso 1 1 calc R . .
C18 C 0.1864(5) 0.1140(5) 0.4969(4) 0.0768(17) Uani 1 1 d . . .
H18 H 0.1804 0.0324 0.5383 0.092 Uiso 1 1 calc R . .
C19 C 0.1366(5) 0.1453(4) 0.4026(4) 0.0624(13) Uani 1 1 d . . .
H19 H 0.0978 0.0858 0.3793 0.075 Uiso 1 1 calc R . .
C20 C -0.1259(4) 0.5157(3) 0.2737(3) 0.0408(8) Uani 1 1 d . . .
H20A H -0.2347 0.4795 0.2762 0.049 Uiso 1 1 calc R . .
H20B H -0.0926 0.4741 0.3397 0.049 Uiso 1 1 calc R . .
C21 C -0.1370(5) 0.6478(4) 0.2592(3) 0.0453(9) Uani 1 1 d . . .
H21A H -0.2543 0.6634 0.2817 0.054 Uiso 1 1 calc R . .
H21B H -0.0742 0.6690 0.3048 0.054 Uiso 1 1 calc R . .
C22 C -0.0717(4) 0.7250(3) 0.1500(3) 0.0410(9) Uani 1 1 d . . .
C23 C -0.0998(6) 0.8545(4) 0.1192(4) 0.0602(12) Uani 1 1 d . . .
H23A H -0.0463 0.8930 0.0455 0.090 Uiso 1 1 calc R . .
H23B H -0.0526 0.8908 0.1621 0.090 Uiso 1 1 calc R . .
H23C H -0.2190 0.8648 0.1298 0.090 Uiso 1 1 calc R . .
C24 C 0.3171(6) 0.7175(7) 0.3820(4) 0.092(2) 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'
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'
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'
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
C20 Pd1 O1 82.88(13) . . ?
C20 Pd1 N2 179.11(13) . . ?
O1 Pd1 N2 97.98(11) . . ?
C20 Pd1 P1 93.46(11) . . ?
O1 Pd1 P1 175.92(7) . . ?
N2 Pd1 P1 85.69(9) . . ?
O2 S1 O3 113.5(2) . . ?
O2 S1 O4 113.9(3) . . ?
O3 S1 O4 116.7(3) . . ?
O2 S1 C24 104.2(3) . . ?
O3 S1 C24 103.2(3) . . ?
O4 S1 C24 103.2(3) . . ?
N1 P1 C8 105.45(18) . . ?
N1 P1 C14 108.34(17) . . ?
C8 P1 C14 105.07(18) . . ?
N1 P1 Pd1 100.71(12) . . ?
C8 P1 Pd1 117.03(12) . . ?
C14 P1 Pd1 119.12(14) . . ?
C22 O1 Pd1 112.6(2) . . ?
C7 N1 C1 105.7(3) . . ?
C7 N1 P1 118.1(2) . . ?
C1 N1 P1 136.0(3) . . ?
C7 N2 C6 114.5(3) . . ?
C7 N2 Pd1 112.8(3) . . ?
C6 N2 Pd1 132.7(3) . . ?
C2 C1 N1 110.3(4) . . ?
C1 C2 C3 108.5(4) . . ?
C4 C3 C7 116.5(4) . . ?
C4 C3 C2 137.9(4) . . ?
C7 C3 C2 105.5(4) . . ?
C5 C4 C3 117.3(4) . . ?
C4 C5 C6 121.2(4) . . ?
N2 C6 C5 123.1(4) . . ?
N2 C7 N1 122.6(3) . . ?
N2 C7 C3 127.4(4) . . ?
N1 C7 C3 110.0(3) . . ?
C13 C8 C9 119.7(4) . . ?
C13 C8 P1 117.4(3) . . ?
C9 C8 P1 122.4(3) . . ?
C10 C9 C8 119.2(4) . . ?
C11 C10 C9 120.9(4) . . ?
C10 C11 C12 120.5(4) . . ?
C11 C12 C13 119.3(5) . . ?
C8 C13 C12 120.4(4) . . ?
C19 C14 C15 120.1(4) . . ?
C19 C14 P1 121.2(3) . . ?
C15 C14 P1 118.6(3) . . ?
C14 C15 C16 120.0(4) . . ?
C17 C16 C15 119.3(5) . . ?
C18 C17 C16 120.8(4) . . ?
C17 C18 C19 120.8(4) . . ?
C14 C19 C18 119.0(5) . . ?
C21 C20 Pd1 107.2(3) . . ?
C22 C21 C20 113.1(3) . . ?
O1 C22 C21 120.3(3) . . ?
O1 C22 C23 120.1(4) . . ?
C21 C22 C23 119.6(4) . . ?
F1 C24 F2 107.4(5) . . ?
F1 C24 F3 108.3(5) . . ?
F2 C24 F3 107.0(6) . . ?
F1 C24 S1 111.8(6) . . ?
F2 C24 S1 111.9(4) . . ?
F3 C24 S1 110.1(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
Pd1 C20 2.029(4) . ?
Pd1 O1 2.102(2) . ?
Pd1 N2 2.137(3) . ?
Pd1 P1 2.1808(10) . ?
S1 O2 1.403(3) . ?
S1 O3 1.429(4) . ?
S1 O4 1.435(4) . ?
S1 C24 1.780(6) . ?
P1 N1 1.716(3) . ?
P1 C8 1.807(4) . ?
P1 C14 1.811(4) . ?
F1 C24 1.313(8) . ?
F2 C24 1.330(6) . ?
F3 C24 1.343(9) . ?
O1 C22 1.238(4) . ?
N1 C7 1.383(5) . ?
N1 C1 1.415(5) . ?
N2 C7 1.332(5) . ?
N2 C6 1.346(5) . ?
C1 C2 1.335(7) . ?
C2 C3 1.430(6) . ?
C3 C4 1.395(6) . ?
C3 C7 1.401(5) . ?
C4 C5 1.383(6) . ?
C5 C6 1.387(6) . ?
C8 C13 1.391(6) . ?
C8 C9 1.393(6) . ?
C9 C10 1.383(6) . ?
C10 C11 1.373(7) . ?
C11 C12 1.379(7) . ?
C12 C13 1.391(5) . ?
C14 C19 1.387(6) . ?
C14 C15 1.397(6) . ?
C15 C16 1.395(6) . ?
C16 C17 1.378(7) . ?
C17 C18 1.371(8) . ?
C18 C19 1.395(7) . ?
C20 C21 1.521(5) . ?
C21 C22 1.482(6) . ?
C22 C23 1.490(6) . ?
