#------------------------------------------------------------------------------
#$Date: 2018-09-09 21:18:12 +0300 (Sun, 09 Sep 2018) $
#$Revision: 210668 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/38/7113849.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_7113849
loop_
_publ_author_name
'Crawforth, Catherine M.'
'Burling, Suzanne'
'Fairlamb, Ian J. S.'
'Taylor, Richard J. K.'
'Whitwood, Adrian C.'
_publ_section_title
;
 Bromobis(triphenylphosphine)(N-succinimide)palladium(II) as a novel
 catalyst for Stille cross-coupling reactions
;
_journal_coden_ASTM              CHCOFS
_journal_issue                   17
_journal_name_full
;
 Chemical Communications (Cambridge, United Kingdom)
;
_journal_page_first              2194
_journal_page_last               2195
_journal_paper_doi               10.1039/b304960d
_journal_year                    2003
_chemical_formula_moiety         'C4 H4 N O2, Br, (P C18 H15)2, Pd '
_chemical_formula_sum            'C40 H34 Br N O2 P2 Pd'
_chemical_formula_weight         808.93
_chemical_name_common
Bromobis(triphenylphosphine)(N-succinimide)palladium(ii)
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 90.182(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.3222(11)
_cell_length_b                   19.880(2)
_cell_length_c                   13.6371(13)
_cell_measurement_reflns_used    1863
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      24.0
_cell_measurement_theta_min      2.5
_cell_volume                     3340.6(6)
_computing_cell_refinement       'SAINT+ v6.22 (Bruker)'
_computing_data_collection       'SMART v5.625 (Bruker)'
_computing_data_reduction        'SAINT+ v6.22 (Bruker)'
_computing_molecular_graphics    'XSHELL v4.02 (Bruker)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      386(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       ω
_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  0.0733
_diffrn_reflns_av_sigmaI/netI    0.0814
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18654
_diffrn_reflns_theta_full        25.06
_diffrn_reflns_theta_max         25.06
_diffrn_reflns_theta_min         1.81
_exptl_absorpt_coefficient_mu    1.885
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.817
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2.03; (Sheldrick)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.608
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.629
_refine_diff_density_min         -0.454
_refine_diff_density_rms         0.106
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.974
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     424
_refine_ls_number_reflns         5900
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.974
_refine_ls_R_factor_all          0.0849
_refine_ls_R_factor_gt           0.0402
_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)+(0.0331P)²+0.0000P] where P==(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0774
_refine_ls_wR_factor_ref         0.0905
_reflns_number_gt                3772
_reflns_number_total             5900
_reflns_threshold_expression     >2sigma(I)
_cod_duplicate_entry             7103858
_cod_data_source_file            b304960d.txt
_cod_data_source_block           ijf0307m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               7113849
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
Pd1 Pd 0.20672(3) 0.168717(19) 0.96047(3) 0.01276(11) Uani 1 1 d .
Br2 Br 0.10210(4) 0.16700(3) 1.11453(3) 0.02084(14) Uani 1 1 d .
P1 P 0.30062(10) 0.16492(7) 0.81684(8) 0.0135(3) Uani 1 1 d .
P2 P 0.31233(10) 0.24797(6) 1.03700(9) 0.0142(3) Uani 1 1 d .
O1 O 0.2412(3) 0.01219(17) 0.9497(2) 0.0228(8) Uani 1 1 d .
C13 C 0.6327(4) 0.1708(3) 0.8144(3) 0.0234(12) Uani 1 1 d .
H13 H 0.6875 0.1972 0.7878 0.028 Uiso 1 1 calc R
N1 N 0.1118(3) 0.09045(19) 0.9125(3) 0.0129(9) Uani 1 1 d .
C30 C 0.1278(4) 0.3304(3) 1.0454(3) 0.0185(11) Uani 1 1 d .
H30 H 0.0919 0.2948 1.0152 0.022 Uiso 1 1 calc R
C34 C 0.2897(4) 0.3793(3) 1.1128(3) 0.0191(12) Uani 1 1 d .
H34 H 0.3635 0.3766 1.1271 0.023 Uiso 1 1 calc R
C18 C 0.2052(4) 0.2870(3) 0.7706(4) 0.0203(12) Uani 1 1 d .
H18 H 0.1673 0.2816 0.8290 0.024 Uiso 1 1 calc R
C24 C 0.3712(4) 0.1363(3) 1.1455(4) 0.0215(12) Uani 1 1 d .
H24 H 0.3563 0.1132 1.0877 0.026 Uiso 1 1 calc R
C22 C 0.3371(4) 0.2483(3) 0.6541(3) 0.0189(12) Uani 1 1 d .
H22 H 0.3868 0.2163 0.6331 0.023 Uiso 1 1 calc R
C17 C 0.2831(4) 0.2395(2) 0.7426(3) 0.0161(11) Uani 1 1 d .
C28 C 0.3872(4) 0.2396(3) 1.2342(3) 0.0194(12) Uani 1 1 d .
H28 H 0.3834 0.2863 1.2368 0.023 Uiso 1 1 calc R
C21 C 0.3171(4) 0.3047(3) 0.5974(4) 0.0248(13) Uani 1 1 d .
H21 H 0.3553 0.3112 0.5394 0.030 Uiso 1 1 calc R
O2 O -0.0477(3) 0.14197(18) 0.8686(3) 0.0260(9) Uani 1 1 d .
C6 C 0.3149(4) 0.0439(3) 0.7061(4) 0.0230(12) Uani 1 1 d .
H6 H 0.3820 0.0365 0.7356 0.028 Uiso 1 1 calc R
C36 C 0.5373(4) 0.2664(3) 1.0085(4) 0.0199(12) Uani 1 1 d .
H36 H 0.5475 0.2337 1.0564 0.024 Uiso 1 1 calc R
C5 C 0.2538(4) 0.1005(2) 0.7309(3) 0.0154(11) Uani 1 1 d .
C27 C 0.4170(4) 0.2040(3) 1.3174(4) 0.0254(13) Uani 1 1 d .
H27 H 0.4325 0.2268 1.3753 0.030 Uiso 1 1 calc R
C1 C 0.1530(4) 0.0263(2) 0.9170(3) 0.0122(11) Uani 1 1 d .
C4 C 0.0088(4) 0.0914(3) 0.8770(3) 0.0186(12) Uani 1 1 d .
C35 C 0.4337(4) 0.2855(2) 0.9821(3) 0.0145(11) Uani 1 1 d .
C26 C 0.4238(4) 0.1348(3) 1.3148(4) 0.0273(13) Uani 1 1 d .
H26 H 0.4434 0.1111 1.3709 0.033 Uiso 1 1 calc R
C12 C 0.5276(4) 0.1868(2) 0.7964(3) 0.0175(12) Uani 1 1 d .
H12 H 0.5111 0.2237 0.7573 0.021 Uiso 1 1 calc R
C8 C 0.1754(5) 0.0086(3) 0.5924(4) 0.0318(14) Uani 1 1 d .
H8 H 0.1497 -0.0220 0.5463 0.038 Uiso 1 1 calc R
C10 C 0.1540(4) 0.1102(3) 0.6851(3) 0.0188(12) Uani 1 1 d .
H10 H 0.1128 0.1479 0.7006 0.023 Uiso 1 1 calc R
C31 C 0.0717(4) 0.3894(3) 1.0660(3) 0.0215(12) Uani 1 1 d .
H31 H -0.0015 0.3927 1.0500 0.026 Uiso 1 1 calc R
C11 C 0.4436(4) 0.1481(3) 0.8364(3) 0.0180(12) Uani 1 1 d .
C3 C -0.0279(4) 0.0215(3) 0.8503(4) 0.0231(13) Uani 1 1 d .
H3A H -0.0468 0.0187 0.7814 0.028 Uiso 1 1 calc R
H3B H -0.0901 0.0081 0.8891 0.028 Uiso 1 1 calc R
C20 C 0.2406(4) 0.3511(3) 0.6267(4) 0.0273(14) Uani 1 1 d .
H20 H 0.2272 0.3888 0.5881 0.033 Uiso 1 1 calc R
C29 C 0.2367(4) 0.3243(2) 1.0694(3) 0.0172(11) Uani 1 1 d .
C7 C 0.2756(4) -0.0010(3) 0.6380(4) 0.0252(13) Uani 1 1 d .
H7 H 0.3167 -0.0386 0.6220 0.030 Uiso 1 1 calc R
C23 C 0.3629(4) 0.2068(2) 1.1474(3) 0.0165(11) Uani 1 1 d .
C15 C 0.5776(4) 0.0768(3) 0.9118(4) 0.0257(13) Uani 1 1 d .
H15 H 0.5949 0.0400 0.9508 0.031 Uiso 1 1 calc R
C33 C 0.2330(4) 0.4376(3) 1.1346(4) 0.0251(13) Uani 1 1 d .
H33 H 0.2680 0.4732 1.1657 0.030 Uiso 1 1 calc R
C32 C 0.1230(4) 0.4427(3) 1.1097(3) 0.0252(13) Uani 1 1 d .
H32 H 0.0850 0.4821 1.1228 0.030 Uiso 1 1 calc R
C25 C 0.4012(4) 0.1007(3) 1.2283(4) 0.0272(14) Uani 1 1 d .
H25 H 0.4062 0.0541 1.2261 0.033 Uiso 1 1 calc R
C19 C 0.1847(4) 0.3423(3) 0.7111(4) 0.0231(12) Uani 1 1 d .
H19 H 0.1322 0.3735 0.7293 0.028 Uiso 1 1 calc R
C16 C 0.4696(4) 0.0925(3) 0.8942(4) 0.0225(12) Uani 1 1 d .
H16 H 0.4149 0.0660 0.9208 0.027 Uiso 1 1 calc R
C37 C 0.6268(4) 0.2959(3) 0.9633(3) 0.0187(12) Uani 1 1 d .
H37 H 0.6966 0.2831 0.9817 0.022 Uiso 1 1 calc R
C2 C 0.0715(4) -0.0225(2) 0.8740(4) 0.0201(12) Uani 1 1 d .
H2A H 0.0531 -0.0573 0.9209 0.024 Uiso 1 1 calc R
H2B H 0.0996 -0.0434 0.8151 0.024 Uiso 1 1 calc R
C40 C 0.4197(4) 0.3345(2) 0.9098(3) 0.0165(11) Uani 1 1 d .
H40 H 0.3501 0.3475 0.8914 0.020 Uiso 1 1 calc R
C14 C 0.6602(4) 0.1156(3) 0.8719(4) 0.0264(13) Uani 1 1 d .
H14 H 0.7326 0.1048 0.8834 0.032 Uiso 1 1 calc R
C9 C 0.1153(4) 0.0647(3) 0.6171(3) 0.0234(13) Uani 1 1 d .
H9 H 0.0481 0.0718 0.5876 0.028 Uiso 1 1 calc R
C39 C 0.5096(4) 0.3640(3) 0.8651(3) 0.0204(12) Uani 1 1 d .
H39 H 0.5001 0.3970 0.8176 0.024 Uiso 1 1 calc R
C38 C 0.6124(4) 0.3440(3) 0.8917(4) 0.0220(13) Uani 1 1 d .
H38 H 0.6725 0.3631 0.8613 0.026 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N1 Pd1 P1 89.50(11)
N1 Pd1 P2 171.18(11)
P1 Pd1 P2 97.18(5)
N1 Pd1 Br2 87.83(10)
P1 Pd1 Br2 177.14(4)
P2 Pd1 Br2 85.37(3)
C17 P1 C11 110.4(2)
C17 P1 C5 100.3(2)
C11 P1 C5 105.6(2)
C17 P1 Pd1 113.19(16)
C11 P1 Pd1 112.07(16)
C5 P1 Pd1 114.48(15)
C23 P2 C35 104.0(2)
C23 P2 C29 110.2(2)
C35 P2 C29 100.2(2)
C23 P2 Pd1 105.05(17)
C35 P2 Pd1 123.79(15)
C29 P2 Pd1 112.96(17)
C12 C13 C14 121.2(5)
C4 N1 C1 112.0(4)
C4 N1 Pd1 129.4(3)
C1 N1 Pd1 118.7(3)
C29 C30 C31 120.5(5)
C33 C34 C29 120.5(5)
C19 C18 C17 119.9(5)
C25 C24 C23 121.0(5)
C21 C22 C17 120.2(5)
C22 C17 C18 118.7(5)
C22 C17 P1 122.2(4)
C18 C17 P1 118.8(4)
C23 C28 C27 121.1(5)
C20 C21 C22 120.0(5)
C7 C6 C5 119.8(5)
C35 C36 C37 120.2(5)
C10 C5 C6 118.7(5)
C10 C5 P1 117.9(4)
C6 C5 P1 123.4(4)
C26 C27 C28 120.3(5)
O1 C1 N1 124.3(4)
O1 C1 C2 126.2(4)
N1 C1 C2 109.4(4)
O2 C4 N1 125.1(5)
O2 C4 C3 124.3(5)
N1 C4 C3 110.6(4)
C36 C35 C40 119.2(4)
C36 C35 P2 122.5(4)
C40 C35 P2 118.2(4)
C27 C26 C25 119.8(5)
C13 C12 C11 120.5(5)
C9 C8 C7 118.5(5)
C9 C10 C5 121.0(5)
C32 C31 C30 120.8(5)
C16 C11 C12 119.1(5)
C16 C11 P1 116.8(4)
C12 C11 P1 124.1(4)
C4 C3 C2 103.7(4)
C19 C20 C21 120.7(5)
C30 C29 C34 118.7(5)
C30 C29 P2 120.5(4)
C34 C29 P2 120.7(4)
C6 C7 C8 121.5(5)
C28 C23 C24 118.0(5)
C28 C23 P2 124.6(4)
C24 C23 P2 117.3(4)
C16 C15 C14 120.8(5)
C34 C33 C32 119.8(5)
C31 C32 C33 119.7(5)
C24 C25 C26 119.8(5)
C20 C19 C18 120.4(5)
C15 C16 C11 119.7(5)
C38 C37 C36 120.3(5)
C1 C2 C3 104.2(4)
C39 C40 C35 120.4(4)
C15 C14 C13 118.8(5)
C10 C9 C8 120.5(5)
C38 C39 C40 119.7(5)
C39 C38 C37 120.3(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Pd1 N1 2.052(4)
Pd1 P1 2.2794(12)
Pd1 P2 2.2928(13)
Pd1 Br2 2.4687(6)
P1 C17 1.807(5)
P1 C11 1.812(5)
P1 C5 1.828(5)
P2 C23 1.821(5)
P2 C35 1.833(5)
P2 C29 1.835(5)
O1 C1 1.206(5)
C13 C12 1.356(7)
C13 C14 1.389(7)
N1 C4 1.357(6)
N1 C1 1.374(6)
C30 C29 1.386(7)
C30 C31 1.390(7)
C34 C33 1.386(7)
C34 C29 1.403(7)
C18 C19 1.389(7)
C18 C17 1.401(7)
C24 C25 1.381(7)
C24 C23 1.406(7)
C22 C21 1.383(7)
C22 C17 1.391(6)
C28 C23 1.383(6)
C28 C27 1.386(7)
C21 C20 1.380(7)
O2 C4 1.227(6)
C6 C7 1.374(7)
C6 C5 1.397(7)
C36 C35 1.378(6)
C36 C37 1.395(6)
C5 C10 1.390(7)
C27 C26 1.377(7)
C1 C2 1.512(6)
C4 C3 1.506(7)
C35 C40 1.396(6)
C26 C25 1.388(7)
C12 C11 1.401(7)
C8 C9 1.381(7)
C8 C7 1.393(7)
C10 C9 1.380(7)
C31 C32 1.369(7)
C11 C16 1.395(7)
C3 C2 1.538(7)
C20 C19 1.354(7)
C15 C16 1.387(7)
C15 C14 1.389(7)
C33 C32 1.400(7)
C37 C38 1.378(7)
C40 C39 1.396(6)
C39 C38 1.375(7)
