#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:26:53 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180299 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/13/7151330.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_7151330
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 H33 Br2 N O P2 Pd S'
_chemical_formula_weight         903.89
_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                 113.582(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   25.775(4)
_cell_length_b                   13.4291(19)
_cell_length_c                   11.7221(16)
_cell_measurement_temperature    293(2)
_cell_volume                     3718.6(9)
_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 0.973
_diffrn_measured_fraction_theta_max 0.931
_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  0.0563
_diffrn_reflns_av_sigmaI/netI    0.0776
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10594
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.01
_diffrn_reflns_theta_min         1.72
_exptl_absorpt_coefficient_mu    2.823
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6282
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.615
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1800
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.17
_refine_diff_density_max         1.344
_refine_diff_density_min         -0.895
_refine_diff_density_rms         0.135
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         4193
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.142
_refine_ls_R_factor_all          0.1219
_refine_ls_R_factor_gt           0.0794
_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)+(0.0534P)²+57.7928P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2022
_refine_ls_wR_factor_ref         0.2156
_reflns_number_gt                2691
_reflns_number_total             4193
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b612235c.txt
_cod_data_source_block           rp21
_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.

'_exptl_absorpt_correction_type' value 'MULTI-SCAN' 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      C2/c
_cod_database_code               7151330
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 0.0000 0.25300(7) 0.7500 0.0404(3) Uani 1 2 d S . .
Br2 Br 0.0000 0.44008(11) 0.7500 0.0719(5) Uani 1 2 d S . .
P1 P 0.09914(9) 0.25221(19) 0.8237(2) 0.0457(6) Uani 1 1 d . . .
C10 C 0.1302(4) 0.3247(7) 0.9649(9) 0.051(2) Uani 1 1 d . . .
C11 C 0.1847(4) 0.3676(8) 1.0080(10) 0.054(2) Uani 1 1 d . . .
H11 H 0.2053 0.3638 0.9588 0.065 Uiso 1 1 calc R . .
C12 C 0.2078(5) 0.4148(9) 1.1209(11) 0.070(3) Uani 1 1 d . . .
H12 H 0.2433 0.4444 1.1465 0.083 Uiso 1 1 calc R . .
C13 C 0.1789(6) 0.4183(11) 1.1953(11) 0.085(4) Uani 1 1 d . . .
H13 H 0.1954 0.4498 1.2722 0.102 Uiso 1 1 calc R . .
C14 C 0.1258(6) 0.3768(14) 1.1608(12) 0.104(5) Uani 1 1 d . . .
H14 H 0.1067 0.3775 1.2134 0.125 Uiso 1 1 calc R . .
C15 C 0.1020(5) 0.3334(10) 1.0420(11) 0.078(4) Uani 1 1 d . . .
H15 H 0.0652 0.3093 1.0141 0.094 Uiso 1 1 calc R . .
C20 C 0.1344(4) 0.1313(8) 0.8677(9) 0.049(2) Uani 1 1 d . . .
C21 C 0.1615(4) 0.1023(9) 0.9940(11) 0.069(3) Uani 1 1 d . . .
H21 H 0.1662 0.1477 1.0573 0.082 Uiso 1 1 calc R . .
C22 C 0.1809(5) 0.0047(12) 1.0221(15) 0.090(5) Uani 1 1 d . . .
H22 H 0.2006 -0.0131 1.1050 0.108 Uiso 1 1 calc R . .
C23 C 0.1720(6) -0.0648(12) 0.9327(17) 0.093(5) Uani 1 1 d . . .
H23 H 0.1832 -0.1304 0.9542 0.112 Uiso 1 1 calc R . .
C24 C 0.1449(5) -0.0360(9) 0.8038(15) 0.081(4) Uani 1 1 d . . .
H24 H 0.1405 -0.0818 0.7411 0.097 Uiso 1 1 calc R . .
C25 C 0.1255(4) 0.0609(8) 0.7743(11) 0.061(3) Uani 1 1 d . . .
H25 H 0.1063 0.0791 0.6914 0.073 Uiso 1 1 calc R . .
C30 C 0.1268(4) 0.2977(7) 0.7100(9) 0.049(2) Uani 1 1 d . . .
C31 C 0.1819(5) 0.2741(8) 0.7293(11) 0.062(3) Uani 1 1 d . . .
H31 H 0.2048 0.2403 0.8011 0.074 Uiso 1 1 calc R . .
C33 C 0.1665(8) 0.3543(10) 0.5365(14) 0.094(5) Uani 1 1 d . . .
H33 H 0.1796 0.3740 0.4767 0.112 Uiso 1 1 calc R . .
C32 C 0.2036(6) 0.3012(9) 0.6400(12) 0.074(3) Uani 1 1 d . . .
H32 H 0.2402 0.2849 0.6495 0.088 Uiso 1 1 calc R . .
C34 C 0.1138(7) 0.3780(10) 0.5184(12) 0.084(4) Uani 1 1 d . . .
H34 H 0.0915 0.4142 0.4483 0.101 Uiso 1 1 calc R . .
C35 C 0.0922(5) 0.3494(7) 0.6024(10) 0.061(3) Uani 1 1 d . . .
H35 H 0.0549 0.3642 0.5884 0.074 Uiso 1 1 calc R . .
S S 0.0154(2) 0.0512(4) 0.8976(6) 0.0474(13) Uani 0.50 1 d P . .
C1 C 0.0000 0.1056(9) 0.7500 0.040(3) Uani 1 2 d S . .
C3 C 0.0006(9) -0.0668(16) 0.830(2) 0.045(5) Uani 0.50 1 d P . .
Br1 Br -0.03846(13) -0.16554(17) 0.5984(2) 0.0665(7) Uani 0.50 1 d P . .
N N -0.0161(7) 0.0389(13) 0.6639(17) 0.040(4) Uani 0.50 1 d P . .
C2 C -0.0162(9) -0.0569(16) 0.708(2) 0.043(5) Uani 0.50 1 d P . .
C4 C 0.0016(13) -0.1555(17) 0.906(3) 0.082(8) Uani 0.50 1 d P . .
H4A H -0.0022 -0.2152 0.8561 0.099 Uiso 0.50 1 calc PR . .
H4B H 0.0377 -0.1587 0.9766 0.099 Uiso 0.50 1 calc PR . .
O O -0.0441(14) -0.1522(16) 0.949(2) 0.153(12) Uani 0.50 1 d P . .
H1 H -0.0735 -0.1345 0.8921 0.230 Uiso 0.50 1 calc PR . .
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'
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 P1 89.74(7) . 2_556 ?
C1 Pd P1 89.74(7) . . ?
P1 Pd P1 179.48(13) 2_556 . ?
C1 Pd Br2 180.000(1) . . ?
P1 Pd Br2 90.26(7) 2_556 . ?
P1 Pd Br2 90.26(7) . . ?
C10 P1 C20 103.4(5) . . ?
C10 P1 C30 109.0(4) . . ?
C20 P1 C30 101.8(4) . . ?
C10 P1 Pd 110.6(3) . . ?
C20 P1 Pd 116.9(3) . . ?
C30 P1 Pd 114.2(3) . . ?
C15 C10 C11 116.2(10) . . ?
C15 C10 P1 119.5(8) . . ?
C11 C10 P1 124.1(8) . . ?
C12 C11 C10 121.4(10) . . ?
C13 C12 C11 119.9(11) . . ?
C12 C13 C14 122.2(12) . . ?
C13 C14 C15 116.5(13) . . ?
C10 C15 C14 123.6(11) . . ?
C25 C20 C21 119.5(10) . . ?
C25 C20 P1 118.2(7) . . ?
C21 C20 P1 121.3(9) . . ?
C22 C21 C20 119.0(13) . . ?
C23 C22 C21 122.1(13) . . ?
C22 C23 C24 119.2(13) . . ?
C25 C24 C23 119.2(14) . . ?
C24 C25 C20 120.7(11) . . ?
C31 C30 C35 120.2(10) . . ?
C31 C30 P1 118.2(8) . . ?
C35 C30 P1 121.5(8) . . ?
C30 C31 C32 120.2(11) . . ?
C34 C33 C32 124.1(13) . . ?
C33 C32 C31 115.8(13) . . ?
C33 C34 C35 120.3(13) . . ?
C34 C35 C30 119.4(12) . . ?
C3 S C1 90.4(9) . . ?
N C1 S 110.7(11) . . ?
N C1 Pd 134.1(9) . . ?
S C1 Pd 114.4(4) . . ?
C2 C3 C4 131(2) . . ?
C2 C3 S 108.5(19) . . ?
C4 C3 S 120.5(19) . . ?
C1 N C2 113.7(17) . . ?
C3 C2 N 117(2) . . ?
C3 C2 Br1 123(2) . . ?
N C2 Br1 120.9(17) . . ?
O C4 C3 111(2) . . ?
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(12) . ?
Pd P1 2.347(2) 2_556 ?
Pd P1 2.347(2) . ?
Pd Br2 2.5123(18) . ?
P1 C10 1.808(10) . ?
P1 C20 1.832(10) . ?
P1 C30 1.849(10) . ?
C10 C15 1.371(15) . ?
C10 C11 1.412(13) . ?
C11 C12 1.370(14) . ?
C12 C13 1.356(18) . ?
C13 C14 1.382(19) . ?
C14 C15 1.403(17) . ?
C20 C25 1.394(15) . ?
C20 C21 1.416(14) . ?
C21 C22 1.394(17) . ?
C22 C23 1.35(2) . ?
C23 C24 1.44(2) . ?
C24 C25 1.387(15) . ?
C30 C31 1.383(14) . ?
C30 C35 1.403(14) . ?
C31 C32 1.419(15) . ?
C33 C34 1.33(2) . ?
C33 C32 1.40(2) . ?
C34 C35 1.367(17) . ?
S C3 1.75(2) . ?
S C1 1.770(7) . ?
C1 N 1.288(19) . ?
C3 C2 1.32(3) . ?
C3 C4 1.48(3) . ?
Br1 C2 1.87(2) . ?
N C2 1.39(3) . ?
C4 O 1.46(4) . ?
