#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:26:53 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180299 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/13/7151327.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_7151327
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            'C43 H36 Br2 Cl2 O2 P2 Pd S'
_chemical_formula_weight         1015.84
_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                96.201(2)
_cell_angle_beta                 105.5040(10)
_cell_angle_gamma                113.5420(10)
_cell_formula_units_Z            2
_cell_length_a                   11.5181(9)
_cell_length_b                   11.8484(9)
_cell_length_c                   18.2094(14)
_cell_measurement_temperature    293(2)
_cell_volume                     2129.4(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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 0.919
_diffrn_measured_fraction_theta_max 0.856
_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  0.0329
_diffrn_reflns_av_sigmaI/netI    0.1100
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            12633
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.02
_diffrn_reflns_theta_min         1.93
_exptl_absorpt_coefficient_mu    2.597
_exptl_absorpt_correction_T_max  0.771
_exptl_absorpt_correction_T_min  0.519
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.584
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1012
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.940
_refine_diff_density_min         -0.676
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.851
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     479
_refine_ls_number_reflns         8817
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.851
_refine_ls_R_factor_all          0.0953
_refine_ls_R_factor_gt           0.0471
_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)+(0.0375P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0894
_refine_ls_wR_factor_ref         0.0989
_reflns_number_gt                4917
_reflns_number_total             8817
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b612235c.txt
_cod_data_source_block           rp16
_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               7151327
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 1.02486(4) 0.84054(4) 0.28190(2) 0.03558(12) Uani 1 1 d . . .
Br2 Br 1.26668(6) 0.99657(5) 0.32755(4) 0.06163(19) Uani 1 1 d . . .
Br1 Br 0.81662(7) 0.70536(6) 0.07180(3) 0.0671(2) Uani 1 1 d . . .
P1 P 0.96040(13) 1.00394(12) 0.28389(7) 0.0359(3) Uani 1 1 d . . .
P2 P 1.08285(14) 0.67218(12) 0.28103(8) 0.0385(3) Uani 1 1 d . . .
S S 0.73256(14) 0.64438(12) 0.28790(8) 0.0452(3) Uani 1 1 d . . .
O1 O 0.3775(5) 0.3721(4) 0.1559(3) 0.0873(14) Uani 1 1 d . . .
O2 O 0.4777(4) 0.4495(4) 0.2860(3) 0.0770(13) Uani 1 1 d . . .
C1 C 0.8280(5) 0.7125(4) 0.2329(3) 0.0380(12) Uani 1 1 d . . .
C2 C 0.7519(5) 0.6597(5) 0.1563(3) 0.0442(13) Uani 1 1 d . . .
C3 C 0.6195(6) 0.5653(5) 0.1389(3) 0.0494(14) Uani 1 1 d . . .
H3 H 0.5580 0.5218 0.0886 0.059 Uiso 1 1 calc R . .
C4 C 0.5949(6) 0.5472(5) 0.2072(3) 0.0498(14) Uani 1 1 d . . .
C5 C 0.4713(6) 0.4481(6) 0.2114(4) 0.0594(16) Uani 1 1 d . . .
C6 C 0.3668(8) 0.3479(6) 0.2967(5) 0.115(3) Uani 1 1 d . . .
H6A H 0.2838 0.3481 0.2679 0.172 Uiso 1 1 calc R . .
H6B H 0.3775 0.3597 0.3515 0.172 Uiso 1 1 calc R . .
H6C H 0.3650 0.2682 0.2777 0.172 Uiso 1 1 calc R . .
C10 C 0.7910(5) 0.9638(5) 0.2855(3) 0.0426(13) Uani 1 1 d . . .
C11 C 0.7698(7) 0.9963(5) 0.3553(4) 0.0623(17) Uani 1 1 d . . .
H11 H 0.8427 1.0417 0.4014 0.075 Uiso 1 1 calc R . .
C12 C 0.6405(9) 0.9607(7) 0.3555(5) 0.088(2) Uani 1 1 d . . .
H12 H 0.6260 0.9812 0.4019 0.106 Uiso 1 1 calc R . .
C13 C 0.5324(8) 0.8946(8) 0.2867(6) 0.098(3) Uani 1 1 d . . .
H13 H 0.4452 0.8720 0.2867 0.118 Uiso 1 1 calc R . .
C14 C 0.5528(7) 0.8626(6) 0.2188(5) 0.081(2) Uani 1 1 d . . .
H14 H 0.4797 0.8172 0.1727 0.098 Uiso 1 1 calc R . .
C15 C 0.6823(6) 0.8975(5) 0.2184(4) 0.0566(15) Uani 1 1 d . . .
H15 H 0.6956 0.8755 0.1718 0.068 Uiso 1 1 calc R . .
C21 C 1.1196(6) 1.1160(5) 0.4408(3) 0.0593(16) Uani 1 1 d . . .
H21 H 1.1075 1.0343 0.4437 0.071 Uiso 1 1 calc R . .
C20 C 1.0658(5) 1.1377(5) 0.3689(3) 0.0387(12) Uani 1 1 d . . .
C22 C 1.1903(7) 1.2130(6) 0.5079(3) 0.076(2) Uani 1 1 d . . .
H22 H 1.2207 1.1955 0.5560 0.091 Uiso 1 1 calc R . .
C23 C 1.2159(6) 1.3344(6) 0.5043(3) 0.0665(18) Uani 1 1 d . . .
H23 H 1.2663 1.4004 0.5493 0.080 Uiso 1 1 calc R . .
C24 C 1.1669(6) 1.3582(5) 0.4340(3) 0.0627(17) Uani 1 1 d . . .
H24 H 1.1844 1.4410 0.4312 0.075 Uiso 1 1 calc R . .
C25 C 1.0910(5) 1.2603(5) 0.3664(3) 0.0471(14) Uani 1 1 d . . .
H25 H 1.0571 1.2781 0.3190 0.057 Uiso 1 1 calc R . .
C30 C 0.9650(5) 1.0681(4) 0.1975(3) 0.0369(12) Uani 1 1 d . . .
C31 C 1.0504(5) 1.0592(5) 0.1594(3) 0.0499(14) Uani 1 1 d . . .
H31 H 1.1055 1.0214 0.1782 0.060 Uiso 1 1 calc R . .
C32 C 1.0548(6) 1.1064(5) 0.0927(3) 0.0622(17) Uani 1 1 d . . .
H32 H 1.1145 1.1023 0.0680 0.075 Uiso 1 1 calc R . .
C33 C 0.9713(6) 1.1586(5) 0.0640(3) 0.0585(16) Uani 1 1 d . . .
H33 H 0.9721 1.1870 0.0184 0.070 Uiso 1 1 calc R . .
C34 C 0.8863(6) 1.1701(5) 0.1012(3) 0.0581(16) Uani 1 1 d . . .
H34 H 0.8306 1.2070 0.0816 0.070 Uiso 1 1 calc R . .
C35 C 0.8847(6) 1.1257(5) 0.1683(3) 0.0544(15) Uani 1 1 d . . .
H35 H 0.8285 1.1347 0.1944 0.065 Uiso 1 1 calc R . .
C40 C 1.2305(5) 0.6995(5) 0.3626(3) 0.0451(13) Uani 1 1 d . . .
C41 C 1.3204(5) 0.6533(5) 0.3532(3) 0.0538(15) Uani 1 1 d . . .
H41 H 1.3053 0.6081 0.3038 0.065 Uiso 1 1 calc R . .
C42 C 1.4311(7) 0.6723(6) 0.4150(4) 0.0779(19) Uani 1 1 d . . .
H42 H 1.4899 0.6407 0.4068 0.093 Uiso 1 1 calc R . .
C43 C 1.4547(8) 0.7369(7) 0.4874(5) 0.090(2) Uani 1 1 d . . .
H43 H 1.5298 0.7500 0.5291 0.108 Uiso 1 1 calc R . .
C44 C 1.3680(9) 0.7831(7) 0.4995(4) 0.098(3) Uani 1 1 d . . .
H44 H 1.3827 0.8253 0.5497 0.118 Uiso 1 1 calc R . .
C45 C 1.2570(7) 0.7667(6) 0.4362(4) 0.081(2) Uani 1 1 d . . .
H45 H 1.2008 0.8017 0.4442 0.097 Uiso 1 1 calc R . .
C50 C 0.9529(6) 0.5218(5) 0.2849(3) 0.0486(14) Uani 1 1 d . . .
C51 C 0.8484(6) 0.4396(5) 0.2179(4) 0.0552(15) Uani 1 1 d . . .
H51 H 0.8481 0.4551 0.1689 0.066 Uiso 1 1 calc R . .
C52 C 0.7449(6) 0.3348(6) 0.2240(5) 0.0742(19) Uani 1 1 d . . .
H52 H 0.6751 0.2798 0.1785 0.089 Uiso 1 1 calc R . .
C53 C 0.7423(8) 0.3097(7) 0.2947(6) 0.088(2) Uani 1 1 d . . .
H53 H 0.6714 0.2381 0.2973 0.106 Uiso 1 1 calc R . .
C54 C 0.8437(8) 0.3898(7) 0.3617(5) 0.091(2) Uani 1 1 d . . .
H54 H 0.8420 0.3727 0.4101 0.110 Uiso 1 1 calc R . .
C55 C 0.9494(6) 0.4963(6) 0.3580(4) 0.0663(17) Uani 1 1 d . . .
H55 H 1.0181 0.5511 0.4039 0.080 Uiso 1 1 calc R . .
C60 C 1.1193(5) 0.6332(5) 0.1924(3) 0.0404(12) Uani 1 1 d . . .
C61 C 1.1605(5) 0.7288(5) 0.1525(3) 0.0492(14) Uani 1 1 d . . .
H61 H 1.1628 0.8069 0.1690 0.059 Uiso 1 1 calc R . .
C62 C 1.1980(6) 0.7055(6) 0.0875(3) 0.0592(16) Uani 1 1 d . . .
H62 H 1.2261 0.7686 0.0610 0.071 Uiso 1 1 calc R . .
C63 C 1.1933(6) 0.5912(6) 0.0633(3) 0.0650(17) Uani 1 1 d . . .
H63 H 1.2167 0.5760 0.0194 0.078 Uiso 1 1 calc R . .
C64 C 1.1547(6) 0.4973(6) 0.1024(4) 0.0662(18) Uani 1 1 d . . .
H64 H 1.1541 0.4199 0.0859 0.079 Uiso 1 1 calc R . .
C65 C 1.1169(6) 0.5184(5) 0.1663(3) 0.0528(15) Uani 1 1 d . . .
H65 H 1.0893 0.4543 0.1921 0.063 Uiso 1 1 calc R . .
Cl1 Cl 0.3989(3) 0.0614(2) 0.10706(17) 0.1632(11) Uani 1 1 d . . .
Cl2 Cl 0.5150(3) 0.2111(4) 0.00532(16) 0.1839(13) Uani 1 1 d . . .
C7 C 0.3798(7) 0.1441(7) 0.0360(4) 0.104(3) Uani 1 1 d . . .
H7A H 0.3022 0.0868 -0.0094 0.125 Uiso 1 1 calc R . .
H7B H 0.3600 0.2110 0.0562 0.125 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
Pd Pd -0.9988 1.0072 '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'
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'
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'
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 89.34(12) . . ?
C1 Pd P2 89.05(13) . . ?
P1 Pd P2 177.96(5) . . ?
C1 Pd Br2 173.92(13) . . ?
P1 Pd Br2 91.06(4) . . ?
P2 Pd Br2 90.68(4) . . ?
C20 P1 C10 102.9(2) . . ?
C20 P1 C30 106.4(2) . . ?
C10 P1 C30 104.1(2) . . ?
C20 P1 Pd 113.88(16) . . ?
C10 P1 Pd 116.78(16) . . ?
C30 P1 Pd 111.68(15) . . ?
C40 P2 C60 105.2(2) . . ?
C40 P2 C50 103.3(2) . . ?
C60 P2 C50 104.8(2) . . ?
C40 P2 Pd 114.96(17) . . ?
C60 P2 Pd 112.29(16) . . ?
C50 P2 Pd 115.16(16) . . ?
C1 S C4 93.4(3) . . ?
C5 O2 C6 115.5(6) . . ?
C2 C1 S 108.1(4) . . ?
C2 C1 Pd 129.4(4) . . ?
S C1 Pd 122.4(3) . . ?
C1 C2 C3 117.3(5) . . ?
C1 C2 Br1 123.4(4) . . ?
C3 C2 Br1 119.4(4) . . ?
C4 C3 C2 109.7(5) . . ?
C3 C4 C5 124.4(6) . . ?
C3 C4 S 111.6(4) . . ?
C5 C4 S 123.7(5) . . ?
O1 C5 O2 123.5(6) . . ?
O1 C5 C4 125.2(6) . . ?
O2 C5 C4 111.2(6) . . ?
C15 C10 C11 119.1(5) . . ?
C15 C10 P1 119.9(4) . . ?
C11 C10 P1 121.0(5) . . ?
C12 C11 C10 119.8(7) . . ?
C11 C12 C13 120.0(7) . . ?
C14 C13 C12 120.3(7) . . ?
C13 C14 C15 119.9(7) . . ?
C10 C15 C14 120.9(6) . . ?
C22 C21 C20 121.3(5) . . ?
C25 C20 C21 117.6(5) . . ?
C25 C20 P1 122.9(4) . . ?
C21 C20 P1 119.4(4) . . ?
C23 C22 C21 120.3(5) . . ?
C22 C23 C24 119.3(5) . . ?
C23 C24 C25 120.9(5) . . ?
C20 C25 C24 120.6(5) . . ?
C31 C30 C35 118.4(4) . . ?
C31 C30 P1 119.3(4) . . ?
C35 C30 P1 122.2(4) . . ?
C30 C31 C32 120.4(5) . . ?
C33 C32 C31 119.7(5) . . ?
C32 C33 C34 121.1(5) . . ?
C33 C34 C35 118.8(5) . . ?
C34 C35 C30 121.5(5) . . ?
C45 C40 C41 117.4(5) . . ?
C45 C40 P2 120.9(4) . . ?
C41 C40 P2 121.7(4) . . ?
C42 C41 C40 121.9(6) . . ?
C43 C42 C41 120.1(6) . . ?
C42 C43 C44 120.0(7) . . ?
C43 C44 C45 120.0(6) . . ?
C40 C45 C44 120.6(6) . . ?
C51 C50 C55 118.6(5) . . ?
C51 C50 P2 121.3(4) . . ?
C55 C50 P2 119.6(5) . . ?
C52 C51 C50 119.8(6) . . ?
C53 C52 C51 121.6(7) . . ?
C52 C53 C54 119.8(7) . . ?
C53 C54 C55 120.3(7) . . ?
C54 C55 C50 119.9(7) . . ?
C65 C60 C61 118.7(5) . . ?
C65 C60 P2 123.4(4) . . ?
C61 C60 P2 117.7(4) . . ?
C62 C61 C60 119.5(5) . . ?
C63 C62 C61 120.0(5) . . ?
C62 C63 C64 121.1(5) . . ?
C63 C64 C65 119.6(5) . . ?
C60 C65 C64 121.1(5) . . ?
Cl2 C7 Cl1 115.9(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
Pd C1 2.029(5) . ?
Pd P1 2.3341(12) . ?
Pd P2 2.3429(12) . ?
Pd Br2 2.4867(7) . ?
Br1 C2 1.919(5) . ?
P1 C20 1.819(5) . ?
P1 C10 1.824(5) . ?
P1 C30 1.824(5) . ?
P2 C40 1.819(5) . ?
P2 C60 1.830(5) . ?
P2 C50 1.837(5) . ?
S C1 1.708(5) . ?
S C4 1.712(6) . ?
O1 C5 1.200(7) . ?
O2 C5 1.338(7) . ?
O2 C6 1.441(7) . ?
C1 C2 1.351(7) . ?
C2 C3 1.408(7) . ?
C3 C4 1.367(7) . ?
C4 C5 1.468(8) . ?
C10 C15 1.366(7) . ?
C10 C11 1.400(7) . ?
C11 C12 1.377(8) . ?
C12 C13 1.382(10) . ?
C13 C14 1.361(9) . ?
C14 C15 1.381(8) . ?
C21 C22 1.376(8) . ?
C21 C20 1.390(6) . ?
C20 C25 1.372(6) . ?
C22 C23 1.362(7) . ?
C23 C24 1.362(7) . ?
C24 C25 1.390(7) . ?
C30 C31 1.374(6) . ?
C30 C35 1.387(6) . ?
C31 C32 1.396(7) . ?
C32 C33 1.363(7) . ?
C33 C34 1.370(7) . ?
C34 C35 1.383(6) . ?
C40 C45 1.372(7) . ?
C40 C41 1.389(6) . ?
C41 C42 1.375(7) . ?
C42 C43 1.351(8) . ?
C43 C44 1.368(9) . ?
C44 C45 1.403(9) . ?
C50 C51 1.381(7) . ?
C50 C55 1.403(7) . ?
C51 C52 1.376(8) . ?
C52 C53 1.357(9) . ?
C53 C54 1.363(9) . ?
C54 C55 1.384(9) . ?
C60 C65 1.378(6) . ?
C60 C61 1.403(6) . ?
C61 C62 1.400(7) . ?
C62 C63 1.354(7) . ?
C63 C64 1.374(7) . ?
C64 C65 1.379(7) . ?
Cl1 C7 1.725(7) . ?
Cl2 C7 1.715(7) . ?
