#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:26:53 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180299 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/13/7151328.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_7151328
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            'C40 H32 Br2 P2 Pd S'
_chemical_formula_weight         872.88
_chemical_name_systematic
;
?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 113.7810(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   25.7511(18)
_cell_length_b                   13.0925(9)
_cell_length_c                   11.5739(8)
_cell_measurement_temperature    293(2)
_cell_volume                     3570.8(4)
_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 0.942
_diffrn_measured_fraction_theta_max 0.942
_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  0.0399
_diffrn_reflns_av_sigmaI/netI    0.0597
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10568
_diffrn_reflns_theta_full        28.06
_diffrn_reflns_theta_max         28.06
_diffrn_reflns_theta_min         1.78
_exptl_absorpt_coefficient_mu    2.934
_exptl_absorpt_correction_T_max  0.495
_exptl_absorpt_correction_T_min  0.341
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.624
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1736
_exptl_crystal_size_max          .31
_exptl_crystal_size_mid          .26
_exptl_crystal_size_min          .24
_refine_diff_density_max         1.191
_refine_diff_density_min         -1.234
_refine_diff_density_rms         0.128
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.157
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         4089
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.157
_refine_ls_R_factor_all          0.1024
_refine_ls_R_factor_gt           0.0709
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0546P)²+55.2417P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2024
_refine_ls_wR_factor_ref         0.2102
_reflns_number_gt                2692
_reflns_number_total             4089
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b612235c.txt
_cod_data_source_block           rp17
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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      C2/c
_cod_database_code               7151328
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
Pd Pd 0.5000 0.75563(7) 0.2500 0.0391(3) Uani 1 2 d S . .
Br2 Br 0.5000 0.56416(12) 0.2500 0.0717(5) Uani 1 2 d S . .
Br1 Br 0.4839(2) 1.2054(2) 0.1617(5) 0.1528(19) Uani 0.50 1 d P . .
P1 P 0.59826(8) 0.75627(19) 0.32184(19) 0.0430(5) Uani 1 1 d . . .
S S 0.5246(3) 0.9535(4) 0.4266(6) 0.0725(16) Uani 0.50 1 d P . .
C1 C 0.5042(7) 0.9069(14) 0.2930(15) 0.046(5) Uani 0.50 1 d P . .
C2 C 0.4889(8) 0.988(2) 0.194(2) 0.070(7) Uani 0.50 1 d P . .
H2 H 0.4741 0.9765 0.1077 0.084 Uiso 0.50 1 calc PR . .
C3 C 0.5000 1.0789(19) 0.2500 0.092(6) Uani 1 2 d S . .
C4 C 0.5171(11) 1.0838(15) 0.382(4) 0.093(10) Uani 0.50 1 d P . .
H4 H 0.5230 1.1412 0.4336 0.112 Uiso 0.50 1 calc PR . .
C10 C 0.6337(3) 0.8792(7) 0.3633(9) 0.048(2) Uani 1 1 d . . .
C11 C 0.6636(5) 0.9105(9) 0.4868(11) 0.074(3) Uani 1 1 d . . .
H11 H 0.6708 0.8639 0.5520 0.088 Uiso 1 1 calc R . .
C12 C 0.6831(6) 1.0108(12) 0.5152(15) 0.097(5) Uani 1 1 d . . .
H12 H 0.7028 1.0311 0.5986 0.116 Uiso 1 1 calc R . .
C14 C 0.6464(5) 1.0496(10) 0.2979(14) 0.083(4) Uani 1 1 d . . .
H14 H 0.6418 1.0961 0.2338 0.099 Uiso 1 1 calc R . .
C13 C 0.6733(6) 1.0768(11) 0.4217(18) 0.104(6) Uani 1 1 d . . .
H13 H 0.6852 1.1441 0.4413 0.125 Uiso 1 1 calc R . .
C15 C 0.6261(4) 0.9509(8) 0.2703(11) 0.061(3) Uani 1 1 d . . .
H15 H 0.6066 0.9321 0.1862 0.073 Uiso 1 1 calc R . .
C20 C 0.6258(4) 0.7083(7) 0.2109(8) 0.046(2) Uani 1 1 d . . .
C21 C 0.5909(5) 0.6531(9) 0.1041(10) 0.069(3) Uani 1 1 d . . .
H21 H 0.5542 0.6346 0.0917 0.083 Uiso 1 1 calc R . .
C22 C 0.6135(7) 0.6273(12) 0.0177(13) 0.102(5) Uani 1 1 d . . .
H22 H 0.5898 0.5962 -0.0574 0.123 Uiso 1 1 calc R . .
C23 C 0.6671(7) 0.6444(10) 0.0363(13) 0.087(4) Uani 1 1 d . . .
H23 H 0.6806 0.6216 -0.0226 0.105 Uiso 1 1 calc R . .
C24 C 0.7033(5) 0.6963(9) 0.1436(12) 0.071(3) Uani 1 1 d . . .
H24 H 0.7407 0.7100 0.1569 0.086 Uiso 1 1 calc R . .
C25 C 0.6815(4) 0.7271(8) 0.2304(10) 0.058(2) Uani 1 1 d . . .
H25 H 0.7051 0.7612 0.3032 0.070 Uiso 1 1 calc R . .
C30 C 0.6290(4) 0.6844(8) 0.4683(8) 0.050(2) Uani 1 1 d . . .
C31 C 0.6815(4) 0.6375(8) 0.5078(9) 0.057(3) Uani 1 1 d . . .
H31 H 0.7015 0.6389 0.4566 0.068 Uiso 1 1 calc R . .
C32 C 0.7042(5) 0.5883(10) 0.6238(11) 0.075(3) Uani 1 1 d . . .
H32 H 0.7392 0.5560 0.6494 0.090 Uiso 1 1 calc R . .
C33 C 0.6752(5) 0.5868(12) 0.7017(12) 0.091(4) Uani 1 1 d . . .
H33 H 0.6907 0.5548 0.7800 0.109 Uiso 1 1 calc R . .
C34 C 0.6227(5) 0.6341(12) 0.6608(11) 0.093(5) Uani 1 1 d . . .
H34 H 0.6025 0.6337 0.7117 0.112 Uiso 1 1 calc R . .
C35 C 0.6002(4) 0.6820(11) 0.5437(10) 0.076(3) Uani 1 1 d . . .
H35 H 0.5648 0.7129 0.5167 0.091 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'
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'
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'
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 C1 26.4(9) . 2_655 ?
C1 Pd P1 91.5(5) . 2_655 ?
C1 Pd P1 88.1(5) 2_655 2_655 ?
C1 Pd P1 88.1(5) . . ?
C1 Pd P1 91.5(5) 2_655 . ?
P1 Pd P1 179.59(13) 2_655 . ?
C1 Pd Br2 166.8(4) . . ?
C1 Pd Br2 166.8(4) 2_655 . ?
P1 Pd Br2 90.21(7) 2_655 . ?
P1 Pd Br2 90.21(7) . . ?
C4 Br1 Br1 106.3(14) 2_655 2_655 ?
C4 Br1 C3 46.1(15) 2_655 . ?
Br1 Br1 C3 60.6(4) 2_655 . ?
C20 P1 C10 101.2(4) . . ?
C20 P1 C30 109.5(4) . . ?
C10 P1 C30 103.2(4) . . ?
C20 P1 Pd 115.3(3) . . ?
C10 P1 Pd 117.2(3) . . ?
C30 P1 Pd 109.5(3) . . ?
C2 S C1 42.7(10) 2_655 . ?
C2 S C4 55.8(14) 2_655 . ?
C1 S C4 97.9(14) . . ?
C1 C1 C2 95.7(18) 2_655 2_655 ?
C1 C1 C2 45.9(13) 2_655 . ?
C2 C1 C2 52(3) 2_655 . ?
C1 C1 S 155.6(11) 2_655 . ?
C2 C1 S 60.2(18) 2_655 . ?
C2 C1 S 111.4(16) . . ?
C1 C1 Pd 76.8(4) 2_655 . ?
C2 C1 Pd 169(2) 2_655 . ?
C2 C1 Pd 122.2(15) . . ?
S C1 Pd 126.4(8) . . ?
C3 C2 C1 109(2) . . ?
C2 C3 C2 52.6(18) . 2_655 ?
C2 C3 C4 118(2) . . ?
C2 C3 C4 66.7(12) 2_655 . ?
C2 C3 C4 66.7(12) . 2_655 ?
C2 C3 C4 118(2) 2_655 2_655 ?
C4 C3 C4 175(3) . 2_655 ?
C2 C3 Br1 176.7(12) . 2_655 ?
C2 C3 Br1 124.3(8) 2_655 2_655 ?
C4 C3 Br1 58.2(11) . 2_655 ?
C4 C3 Br1 116.6(17) 2_655 2_655 ?
C2 C3 Br1 124.3(8) . . ?
C2 C3 Br1 176.7(12) 2_655 . ?
C4 C3 Br1 116.6(17) . . ?
C4 C3 Br1 58.2(11) 2_655 . ?
Br1 C3 Br1 58.9(8) 2_655 . ?
C3 C4 S 102.7(18) . . ?
C15 C10 C11 116.7(10) . . ?
C15 C10 P1 119.9(7) . . ?
C11 C10 P1 123.1(9) . . ?
C10 C11 C12 121.3(13) . . ?
C11 C12 C13 119.2(13) . . ?
C12 C13 C14 122.4(13) . . ?
C13 C14 C15 118.2(14) . . ?
C10 C15 C14 122.2(11) . . ?
C21 C20 C25 119.4(9) . . ?
C25 C20 P1 120.0(7) . . ?
C21 C20 P1 120.6(8) . . ?
C20 C21 C22 117.2(11) . . ?
C21 C22 C23 123.5(12) . . ?
C22 C23 C24 120.3(11) . . ?
C25 C24 C23 117.8(12) . . ?
C20 C25 C24 121.5(10) . . ?
C35 C30 C34 119.5(9) . . ?
C35 C30 P1 117.8(8) . . ?
C31 C30 P1 122.6(7) . . ?
C30 C31 C32 120.1(10) . . ?
C31 C32 C33 120.6(11) . . ?
C32 C33 C34 118.7(11) . . ?
C33 C34 C35 120.0(12) . . ?
C30 C35 C34 121.2(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
Pd C1 2.03(2) . ?
Pd C1 2.03(2) 2_655 ?
Pd P 2.323(2) 2_655 ?
Pd P 2.323(2) . ?
Pd Br2 2.5068(18) . ?
Br1 C4 1.67(2) 2_655 ?
Br1 Br1 1.871(11) 2_655 ?
Br1 C3 1.90(2) . ?
Br1 C3 1.90(2) 2_655 ?
P1 C20 1.812(9) . ?
P1 C10 1.817(9) . ?
P1 C30 1.818(9) . ?
S C2 1.38(3) 2_655 ?
S C1 1.54(2) . ?
S C4 1.77(2) . ?
C1 C1 0.93(3) 2_655 ?
C1 C2 1.490(19) . ?
C1 C2 1.07(3) 2_655 ?
C2 C3 1.33(3) . ?
C2 C3 1.33(3) 2_655 ?
C3 C4 1.42(4) . ?
C3 C4 1.42(4) 2_655 ?
C10 C15 1.381(14) . ?
C10 C11 1.384(13) . ?
C11 C12 1.398(17) . ?
C12 C13 1.33(2) . ?
C13 C14 1.36(2) . ?
C14 C15 1.382(15) . ?
C20 C25 1.381(13) . ?
C20 C21 1.400(13) . ?
C21 C22 1.385(17) . ?
C22 C23 1.328(19) . ?
C23 C24 1.393(18) . ?
C24 C25 1.391(14) . ?
C30 C35 1.355(14) . ?
C30 C31 1.382(13) . ?
C31 C32 1.388(14) . ?
C32 C33 1.383(17) . ?
C33 C34 1.385(17) . ?
C34 C35 1.390(16) . ?
