#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:26:53 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180299 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/13/7151329.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_7151329
loop_
_publ_author_name
'Pereira, Raquel'
'Furst, Audrey'
'Iglesias, Beatriz'
'Germain, Pierre'
'Gronemeyer, Hinrich'
'de Lera, Angel R.'
_publ_section_title
;
 Insights into the mechanism of the site-selective sequential
 palladium-catalyzed cross-coupling reactions of
 dibromothiophenes/dibromothiazoles and arylboronic acids. Synthesis of
 PPARbeta/delta agonists.
;
_journal_issue                   24
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              4514
_journal_page_last               4525
_journal_paper_doi               10.1039/b612235c
_journal_volume                  4
_journal_year                    2006
_chemical_formula_sum            'C42 H34 Br2 Cl3 N O2 P2 Pd S'
_chemical_formula_weight         1051.27
_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                90.3990(10)
_cell_angle_beta                 105.424(2)
_cell_angle_gamma                98.5010(10)
_cell_formula_units_Z            2
_cell_length_a                   11.6242(8)
_cell_length_b                   11.8469(9)
_cell_length_c                   16.6140(13)
_cell_measurement_temperature    293(2)
_cell_volume                     2178.7(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.917
_diffrn_measured_fraction_theta_max 0.848
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_av_sigmaI/netI    0.0891
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12794
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.05
_diffrn_reflns_theta_min         1.74
_exptl_absorpt_coefficient_mu    2.601
_exptl_absorpt_correction_T_max  0.579
_exptl_absorpt_correction_T_min  0.325
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.602
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1044
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.849
_refine_diff_density_min         -1.027
_refine_diff_density_rms         0.113
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.909
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     488
_refine_ls_number_reflns         8973
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.919
_refine_ls_R_factor_all          0.0916
_refine_ls_R_factor_gt           0.0548
_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)+(0.0823P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1358
_refine_ls_wR_factor_ref         0.1539
_reflns_number_gt                5230
_reflns_number_total             8973
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b612235c.txt
_cod_data_source_block           rp20
_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.

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               7151329
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
Pd Pd 0.10075(4) 0.02649(4) 0.26486(3) 0.04195(14) Uani 1 1 d . . .
Br2 Br 0.24938(6) -0.10874(6) 0.30116(5) 0.0612(2) Uani 1 1 d . . .
Br1 Br -0.23213(8) 0.34707(7) 0.24788(5) 0.0767(3) Uani 1 1 d . . .
S S -0.07111(14) 0.12991(14) 0.11165(10) 0.0521(4) Uani 1 1 d . . .
N N -0.0716(4) 0.1931(4) 0.2604(3) 0.0453(12) Uani 1 1 d . . .
O1 O -0.2358(5) 0.2198(4) -0.0227(3) 0.0785(15) Uani 1 1 d . . .
O2 O -0.3115(4) 0.3375(4) 0.0476(3) 0.0730(14) Uani 1 1 d . . .
P1 P -0.05430(14) -0.12123(12) 0.26835(10) 0.0435(4) Uani 1 1 d . . .
P2 P 0.25089(14) 0.18133(13) 0.26591(10) 0.0457(4) Uani 1 1 d . . .
C1 C -0.0208(5) 0.1268(5) 0.2197(4) 0.0495(15) Uani 1 1 d . . .
C2 C -0.1502(5) 0.2472(5) 0.2036(4) 0.0466(14) Uani 1 1 d . . .
C3 C -0.1668(5) 0.2253(5) 0.1201(4) 0.0461(14) Uani 1 1 d . . .
C4 C -0.2449(5) 0.2685(5) 0.0458(4) 0.0485(15) Uani 1 1 d . . .
C5 C -0.3057(8) 0.2605(9) -0.1008(5) 0.109(3) Uani 1 1 d . . .
H5A H -0.3822 0.2745 -0.0946 0.163 Uiso 1 1 calc R . .
H5B H -0.3187 0.2036 -0.1451 0.163 Uiso 1 1 calc R . .
H5C H -0.2621 0.3299 -0.1140 0.163 Uiso 1 1 calc R . .
C10 C -0.0891(5) -0.2275(5) 0.1811(4) 0.0497(15) Uani 1 1 d . . .
C11 C -0.1907(6) -0.3102(5) 0.1655(5) 0.0643(19) Uani 1 1 d . . .
H11 H -0.2408 -0.3130 0.2010 0.077 Uiso 1 1 calc R . .
C12 C -0.2196(7) -0.3879(7) 0.0990(5) 0.082(2) Uani 1 1 d . . .
H12 H -0.2889 -0.4423 0.0891 0.098 Uiso 1 1 calc R . .
C13 C -0.1458(8) -0.3844(8) 0.0480(5) 0.088(3) Uani 1 1 d . . .
H13 H -0.1628 -0.4390 0.0042 0.106 Uiso 1 1 calc R . .
C14 C -0.0451(8) -0.3005(7) 0.0602(5) 0.075(2) Uani 1 1 d . . .
H14 H 0.0019 -0.2954 0.0226 0.090 Uiso 1 1 calc R . .
C15 C -0.0156(6) -0.2254(6) 0.1280(4) 0.0582(17) Uani 1 1 d . . .
H15 H 0.0547 -0.1724 0.1384 0.070 Uiso 1 1 calc R . .
C20 C -0.2006(5) -0.0808(5) 0.2635(4) 0.0541(16) Uani 1 1 d . . .
C21 C -0.2374(7) -0.0580(7) 0.3335(5) 0.082(2) Uani 1 1 d . . .
H21 H -0.1888 -0.0676 0.3866 0.098 Uiso 1 1 calc R . .
C22 C -0.3461(9) -0.0210(8) 0.3240(7) 0.101(3) Uani 1 1 d . . .
H22 H -0.3725 -0.0094 0.3712 0.121 Uiso 1 1 calc R . .
C23 C -0.4162(8) -0.0008(10) 0.2484(8) 0.115(4) Uani 1 1 d . . .
H23 H -0.4880 0.0274 0.2440 0.138 Uiso 1 1 calc R . .
C24 C -0.3815(7) -0.0216(7) 0.1793(6) 0.085(2) Uani 1 1 d . . .
H24 H -0.4317 -0.0125 0.1267 0.102 Uiso 1 1 calc R . .
C25 C -0.2762(6) -0.0551(6) 0.1865(5) 0.0635(18) Uani 1 1 d . . .
H25 H -0.2505 -0.0621 0.1385 0.076 Uiso 1 1 calc R . .
C30 C -0.0205(6) -0.1969(5) 0.3648(4) 0.0508(15) Uani 1 1 d . . .
C31 C -0.0580(8) -0.3094(6) 0.3697(5) 0.084(2) Uani 1 1 d . . .
H31 H -0.0990 -0.3532 0.3211 0.101 Uiso 1 1 calc R . .
C32 C -0.0363(11) -0.3609(8) 0.4458(6) 0.123(4) Uani 1 1 d . . .
H32 H -0.0573 -0.4395 0.4479 0.147 Uiso 1 1 calc R . .
C33 C 0.0174(9) -0.2939(9) 0.5194(5) 0.098(3) Uani 1 1 d . . .
H33 H 0.0252 -0.3262 0.5711 0.118 Uiso 1 1 calc R . .
C34 C 0.0564(8) -0.1857(9) 0.5153(5) 0.095(3) Uani 1 1 d . . .
H34 H 0.0965 -0.1426 0.5643 0.114 Uiso 1 1 calc R . .
C35 C 0.0397(7) -0.1334(6) 0.4395(4) 0.074(2) Uani 1 1 d . . .
H35 H 0.0685 -0.0561 0.4382 0.089 Uiso 1 1 calc R . .
C40 C 0.3842(6) 0.1896(5) 0.3534(4) 0.0528(15) Uani 1 1 d . . .
C41 C 0.3781(8) 0.1430(8) 0.4279(5) 0.108(4) Uani 1 1 d . . .
H41 H 0.3046 0.1066 0.4341 0.130 Uiso 1 1 calc R . .
C42 C 0.4826(10) 0.1503(9) 0.4947(6) 0.127(4) Uani 1 1 d . . .
H42 H 0.4779 0.1180 0.5447 0.152 Uiso 1 1 calc R . .
C43 C 0.5887(9) 0.2029(9) 0.4874(6) 0.102(3) Uani 1 1 d . . .
H43 H 0.6570 0.2074 0.5325 0.123 Uiso 1 1 calc R . .
C44 C 0.5975(8) 0.2493(9) 0.4156(6) 0.104(3) Uani 1 1 d . . .
H44 H 0.6704 0.2897 0.4113 0.125 Uiso 1 1 calc R . .
C45 C 0.4962(7) 0.2361(7) 0.3477(5) 0.081(2) Uani 1 1 d . . .
H45 H 0.5049 0.2599 0.2962 0.097 Uiso 1 1 calc R . .
C50 C 0.2077(6) 0.3213(5) 0.2709(5) 0.0589(18) Uani 1 1 d . . .
C51 C 0.2239(8) 0.3770(7) 0.3461(7) 0.093(3) Uani 1 1 d . . .
H51 H 0.2593 0.3439 0.3953 0.111 Uiso 1 1 calc R . .
C52 C 0.1880(12) 0.4824(9) 0.3492(10) 0.139(5) Uani 1 1 d . . .
H52 H 0.2009 0.5201 0.4009 0.166 Uiso 1 1 calc R . .
C53 C 0.1349(13) 0.5318(9) 0.2796(12) 0.145(6) Uani 1 1 d . . .
H53 H 0.1125 0.6034 0.2835 0.174 Uiso 1 1 calc R . .
C54 C 0.1134(9) 0.4771(8) 0.2023(9) 0.117(4) Uani 1 1 d . . .
H54 H 0.0747 0.5096 0.1536 0.141 Uiso 1 1 calc R . .
C55 C 0.1515(7) 0.3718(6) 0.1997(6) 0.082(2) Uani 1 1 d . . .
H55 H 0.1387 0.3340 0.1481 0.098 Uiso 1 1 calc R . .
C60 C 0.3031(5) 0.1793(6) 0.1719(4) 0.0498(15) Uani 1 1 d . . .
C61 C 0.2786(6) 0.0840(6) 0.1221(4) 0.0597(17) Uani 1 1 d . . .
H61 H 0.2299 0.0199 0.1337 0.072 Uiso 1 1 calc R . .
C62 C 0.3260(7) 0.0804(8) 0.0527(5) 0.082(2) Uani 1 1 d . . .
H62 H 0.3102 0.0137 0.0191 0.099 Uiso 1 1 calc R . .
C63 C 0.3955(7) 0.1754(9) 0.0347(5) 0.089(3) Uani 1 1 d . . .
H63 H 0.4270 0.1732 -0.0111 0.106 Uiso 1 1 calc R . .
C64 C 0.4179(7) 0.2704(8) 0.0823(6) 0.083(2) Uani 1 1 d . . .
H64 H 0.4660 0.3342 0.0699 0.100 Uiso 1 1 calc R . .
C65 C 0.3706(6) 0.2764(6) 0.1505(5) 0.068(2) Uani 1 1 d . . .
H65 H 0.3839 0.3447 0.1818 0.082 Uiso 1 1 calc R . .
Cl2 Cl 0.4505(6) 0.6896(6) 0.3056(3) 0.279(3) Uani 1 1 d D . .
Cl1 Cl 0.5560(5) 0.5469(4) 0.2321(6) 0.344(5) Uani 1 1 d D . .
Cl3 Cl 0.6159(11) 0.5803(8) 0.4049(6) 0.544(10) Uani 1 1 d D . .
C6 C 0.5170(17) 0.5871(15) 0.3119(10) 0.320(14) Uani 1 1 d D . .
H6 H 0.4528 0.5244 0.3141 0.384 Uiso 1 1 calc R . .
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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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'
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'
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 Pd P1 89.65(17) . . ?
C1 Pd P2 88.25(17) . . ?
P1 Pd P2 176.55(6) . . ?
C1 Pd Br2 172.06(19) . . ?
P1 Pd Br2 89.85(4) . . ?
P2 Pd Br2 92.60(5) . . ?
C3 S C1 90.9(3) . . ?
C1 N C2 108.9(5) . . ?
C4 O1 C5 115.6(6) . . ?
C20 P1 C30 103.1(3) . . ?
C20 P1 C10 103.0(3) . . ?
C30 P1 C10 107.5(3) . . ?
C20 P1 Pd 116.6(2) . . ?
C30 P1 Pd 112.1(2) . . ?
C10 P1 Pd 113.47(19) . . ?
C50 P2 C40 102.8(3) . . ?
C50 P2 C60 104.6(3) . . ?
C40 P2 C60 106.2(3) . . ?
C50 P2 Pd 115.8(2) . . ?
C40 P2 Pd 114.7(2) . . ?
C60 P2 Pd 111.7(2) . . ?
N C1 S 113.9(5) . . ?
N C1 Pd 129.3(5) . . ?
S C1 Pd 116.8(4) . . ?
N C2 C3 119.6(5) . . ?
N C2 Br1 116.1(5) . . ?
C3 C2 Br1 124.2(5) . . ?
C2 C3 C4 131.8(6) . . ?
C2 C3 S 106.6(4) . . ?
C4 C3 S 121.6(5) . . ?
O2 C4 O1 124.4(6) . . ?
O2 C4 C3 124.7(6) . . ?
O1 C4 C3 110.9(5) . . ?
C15 C10 C11 118.2(6) . . ?
C15 C10 P1 120.6(5) . . ?
C11 C10 P1 121.2(5) . . ?
C12 C11 C10 121.7(7) . . ?
C13 C12 C11 119.0(7) . . ?
C12 C13 C14 120.8(7) . . ?
C15 C14 C13 119.4(7) . . ?
C14 C15 C10 120.7(6) . . ?
C21 C20 C25 115.9(7) . . ?
C21 C20 P1 123.3(6) . . ?
C25 C20 P1 120.2(5) . . ?
C22 C21 C20 119.3(8) . . ?
C23 C22 C21 122.0(9) . . ?
C24 C23 C22 119.6(9) . . ?
C25 C24 C23 119.7(9) . . ?
C24 C25 C20 123.1(8) . . ?
C31 C30 C35 117.8(6) . . ?
C31 C30 P1 123.7(5) . . ?
C35 C30 P1 118.3(5) . . ?
C30 C31 C32 121.2(8) . . ?
C31 C32 C33 119.5(8) . . ?
C34 C33 C32 119.6(8) . . ?
C33 C34 C35 121.6(8) . . ?
C34 C35 C30 120.1(7) . . ?
C45 C40 C41 116.5(7) . . ?
C45 C40 P2 122.3(6) . . ?
C41 C40 P2 121.1(6) . . ?
C40 C41 C42 120.0(8) . . ?
C43 C42 C41 121.0(8) . . ?
C42 C43 C44 120.3(9) . . ?
C43 C44 C45 118.9(9) . . ?
C40 C45 C44 122.8(8) . . ?
C51 C50 C55 118.0(7) . . ?
C51 C50 P2 120.5(6) . . ?
C55 C50 P2 121.4(6) . . ?
C50 C51 C52 120.1(11) . . ?
C53 C52 C51 121.5(13) . . ?
C52 C53 C54 120.4(11) . . ?
C53 C54 C55 117.5(11) . . ?
C50 C55 C54 122.4(10) . . ?
C61 C60 C65 118.7(6) . . ?
C61 C60 P2 120.6(5) . . ?
C65 C60 P2 120.7(5) . . ?
C60 C61 C62 120.4(7) . . ?
C63 C62 C61 119.8(8) . . ?
C64 C63 C62 120.2(8) . . ?
C63 C64 C65 121.1(8) . . ?
C64 C65 C60 119.7(7) . . ?
Cl2 C6 Cl1 118.8(12) . . ?
Cl2 C6 Cl3 113.8(10) . . ?
Cl1 C6 Cl3 116.2(10) . . ?
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
Pd C1 1.979(6) . ?
Pd P1 2.3321(15) . ?
Pd P2 2.3341(15) . ?
Pd Br2 2.4886(8) . ?
Br1 C2 1.882(6) . ?
P1 C20 1.816(6) . ?
P1 C30 1.821(6) . ?
P1 C10 1.834(6) . ?
P2 C50 1.809(7) . ?
P2 C40 1.811(7) . ?
P2 C60 1.822(6) . ?
S C3 1.728(6) . ?
S C1 1.737(7) . ?
N C1 1.328(7) . ?
N C2 1.363(7) . ?
O1 C4 1.309(8) . ?
O1 C5 1.463(8) . ?
O2 C4 1.210(7) . ?
C3 C4 1.470(8) . ?
C2 C3 1.367(8) . ?
C10 C15 1.380(9) . ?
C10 C11 1.383(8) . ?
C11 C12 1.370(10) . ?
C12 C13 1.354(11) . ?
C13 C14 1.389(10) . ?
C14 C15 1.366(9) . ?
C20 C21 1.379(10) . ?
C20 C25 1.410(9) . ?
C21 C22 1.369(11) . ?
C22 C23 1.347(13) . ?
C23 C24 1.346(13) . ?
C24 C25 1.318(9) . ?
C30 C31 1.350(9) . ?
C30 C35 1.401(9) . ?
C31 C32 1.387(11) . ?
C32 C33 1.395(12) . ?
C33 C34 1.304(11) . ?
C34 C35 1.386(10) . ?
C40 C45 1.363(9) . ?
C40 C41 1.375(9) . ?
C41 C42 1.401(12) . ?
C42 C43 1.333(12) . ?
C43 C44 1.340(12) . ?
C44 C45 1.385(10) . ?
C50 C51 1.364(11) . ?
C50 C55 1.377(10) . ?
C51 C52 1.378(13) . ?
C52 C53 1.341(18) . ?
C53 C54 1.379(17) . ?
C54 C55 1.389(12) . ?
C60 C61 1.344(9) . ?
C60 C65 1.397(9) . ?
C61 C62 1.408(10) . ?
C62 C63 1.368(11) . ?
C63 C64 1.323(11) . ?
C64 C65 1.391(11) . ?
Cl2 C6 1.523(12) . ?
Cl1 C6 1.601(14) . ?
Cl3 C6 1.673(15) . ?
