#------------------------------------------------------------------------------
#$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/45/7104583.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_7104583
loop_
_publ_author_name
'Rauf, Waqar'
'Thompson, Amber L'
'Brown, John M'
_publ_section_title
;
 Comparative catalytic C-H vs. C-Si activation of arenes with Pd
 complexes directed by urea or amide groups.
;
_journal_issue                   26
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              3874
_journal_page_last               3876
_journal_paper_doi               10.1039/b905717j
_journal_volume                  34
_journal_year                    2009
_chemical_formula_moiety         'C12 H12 F2 N3 O Pd, C7 H7 O3 S'
_chemical_formula_sum            'C19 H19 F2 N3 O4 Pd S'
_chemical_formula_weight         529.84
_chemical_melting_point          ?
_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
_audit_creation_date             08-06-13
_audit_creation_method           CRYSTALS_ver_12.86
_cell_angle_alpha                90.7614(17)
_cell_angle_beta                 101.0913(17)
_cell_angle_gamma                100.9648(19)
_cell_formula_units_Z            2
_cell_length_a                   7.2492(2)
_cell_length_b                   8.7969(3)
_cell_length_c                   16.6174(6)
_cell_measurement_reflns_used    4141
_cell_measurement_temperature    150
_cell_measurement_theta_max      27
_cell_measurement_theta_min      5
_cell_volume                     1019.55(6)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1997-2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device       'Nonius KappaCCD'
_diffrn_measurement_device_type  Area
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.043
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            14648
_diffrn_reflns_theta_full        25.614
_diffrn_reflns_theta_max         27.542
_diffrn_reflns_theta_min         5.118
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.062
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.77
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_density_diffrn    1.726
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       needle
_exptl_crystal_F_000             532
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.88
_refine_diff_density_min         -1.10
_refine_ls_extinction_coef       65(8)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   1.0018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4643
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0356
_refine_ls_shift/su_max          0.000343
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
Method= Modified Sheldrick
w=1/[σ²(F²) + ( 0.03P)² + 1.39P]
,where P=(max(Fo²,0) + 2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0862
_refine_ls_wR_factor_gt          0.0815
_refine_ls_wR_factor_ref         0.0862
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              11
_reflns_limit_k_min              -11
_reflns_limit_l_max              21
_reflns_limit_l_min              0
_reflns_number_gt                4061
_reflns_number_total             4643
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   2.18
_oxford_diffrn_Wilson_scale      4.77
_oxford_refine_ls_r_factor_ref   0.0439
_oxford_refine_ls_scale          0.4631(8)
_oxford_reflns_number_all        4643
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_structure_analysis_title 5877
_cod_data_source_file            b905717j.txt
_cod_data_source_block           5
_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 

The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_sg_symbol_H-M      'P -1 '
_cod_original_formula_sum        'C19 H19 F2 N3 O4 Pd1 S1'
_cod_database_code               7104583
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_oxford_atom_site_special_shape
_atom_site_attached_hydrogens
Pd1 Pd 0.29871(3) 0.03499(3) -0.066304(13) 0.0259 1.0000 Uani . . . . . . .
O2 O 0.3721(3) 0.2433(2) -0.00695(12) 0.0304 1.0000 Uani . . . . . . .
C3 C 0.3576(4) 0.2795(3) 0.06463(17) 0.0268 1.0000 Uani . . . . . . .
N4 N 0.2902(3) 0.1799(3) 0.11582(14) 0.0257 1.0000 Uani . . . . . . .
C5 C 0.2193(4) 0.0182(3) 0.10230(17) 0.0239 1.0000 Uani . . . . . . .
C6 C 0.2104(4) -0.0658(3) 0.02911(17) 0.0249 1.0000 Uani . . . . . . .
C7 C 0.1288(4) -0.2248(3) 0.02561(18) 0.0290 1.0000 Uani . . . . . . .
C8 C 0.0634(4) -0.2927(3) 0.09127(19) 0.0306 1.0000 Uani . . . . . . .
F9 F -0.0173(3) -0.4461(2) 0.08693(12) 0.0439 1.0000 Uani . . . . . . .
C10 C 0.0787(4) -0.2071(4) 0.16329(18) 0.0292 1.0000 Uani . . . . . . .
C11 C 0.1555(4) -0.0523(4) 0.16972(18) 0.0287 1.0000 Uani . . . . . . .
F12 F 0.0153(3) -0.2774(2) 0.22792(11) 0.0407 1.0000 Uani . . . . . . .
C13 C 0.4191(5) 0.4465(4) 0.0938(2) 0.0348 1.0000 Uani . . . . . . .
N14 N 0.2296(4) -0.1608(3) -0.13820(15) 0.0304 1.0000 Uani . . . . . . .
C15 C 0.2001(4) -0.2550(4) -0.18923(18) 0.0294 1.0000 Uani . . . . . . .
C16 C 0.1633(5) -0.3769(4) -0.2533(2) 0.0349 1.0000 Uani . . . . . . .
N17 N 0.3850(4) 0.1471(3) -0.16969(16) 0.0317 1.0000 Uani . . . . . . .
C18 C 0.4253(4) 0.1925(4) -0.22903(19) 0.0313 1.0000 Uani . . . . . . .
C19 C 0.4793(6) 0.2505(5) -0.3049(2) 0.0487 1.0000 Uani . . . . . . .
S20 S 0.37636(10) 0.27230(9) 0.34179(4) 0.0288 1.0000 Uani . . . . . . .
O21 O 0.5338(3) 0.3941(3) 0.38059(14) 0.0392 1.0000 Uani . . . . . . .
O22 O 0.4274(3) 0.1221(3) 0.33193(14) 0.0366 1.0000 Uani . . . . . . .
O23 O 0.2726(3) 0.3186(3) 0.26323(12) 0.0346 1.0000 Uani . . . . . . .
C24 C 0.2044(4) 0.2490(4) 0.40590(17) 0.0273 1.0000 Uani . . . . . . .
C25 C 0.0389(5) 0.1338(4) 0.3854(2) 0.0360 1.0000 Uani . . . . . . .
C26 C -0.1018(5) 0.1225(4) 0.4318(2) 0.0398 1.0000 Uani . . . . . . .
C27 C -0.0809(5) 0.2222(4) 0.4999(2) 0.0348 1.0000 Uani . . . . . . .
C28 C 0.0859(5) 0.3333(4) 0.5204(2) 0.0371 1.0000 Uani . . . . . . .
C29 C 0.2280(4) 0.3476(4) 0.47416(19) 0.0330 1.0000 Uani . . . . . . .
C30 C -0.2364(5) 0.2108(5) 0.5488(2) 0.0474 1.0000 Uani . . . . . . .
H71 H 0.1177 -0.2893 -0.0220 0.0350 1.0000 Uiso R . . . . . .
H111 H 0.1664 0.0069 0.2194 0.0343 1.0000 Uiso R . . . . . .
H131 H 0.4001 0.4602 0.1490 0.0542 1.0000 Uiso R . . . . . .
H132 H 0.5523 0.4836 0.0929 0.0541 1.0000 Uiso R . . . . . .
H133 H 0.3412 0.5051 0.0583 0.0538 1.0000 Uiso R . . . . . .
H163 H 0.2207 -0.3405 -0.2983 0.0545 1.0000 Uiso R . . . . . .
H162 H 0.2136 -0.4629 -0.2313 0.0542 1.0000 Uiso R . . . . . .
H161 H 0.0296 -0.4067 -0.2718 0.0545 1.0000 Uiso R . . . . . .
H191 H 0.3665 0.2581 -0.3438 0.0784 1.0000 Uiso R . . . . . .
H192 H 0.5457 0.1792 -0.3259 0.0784 1.0000 Uiso R . . . . . .
H193 H 0.5617 0.3499 -0.2949 0.0783 1.0000 Uiso R . . . . . .
H251 H 0.0216 0.0652 0.3401 0.0429 1.0000 Uiso R . . . . . .
H261 H -0.2142 0.0461 0.4172 0.0480 1.0000 Uiso R . . . . . .
H281 H 0.1033 0.4001 0.5669 0.0461 1.0000 Uiso R . . . . . .
H291 H 0.3397 0.4241 0.4888 0.0399 1.0000 Uiso R . . . . . .
H301 H -0.1927 0.2764 0.5979 0.0765 1.0000 Uiso R . . . . . .
H302 H -0.2741 0.1068 0.5649 0.0762 1.0000 Uiso R . . . . . .
H303 H -0.3472 0.2402 0.5173 0.0764 1.0000 Uiso R . . . . . .
H41 H 0.2868 0.2171 0.1632 0.0321 1.0000 Uiso R . . . . . .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476
0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Pd -0.9988 1.0072 19.3319 0.6987 15.5017 7.9893 5.2954 25.2052 0.6058 76.8986
5.2659 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
S 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720
0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
Pd1 2_655 Pd1 . O2 . 83.21(6) yes
Pd1 2_655 Pd1 . C6 . 72.97(8) yes
O2 . Pd1 . C6 . 92.26(10) yes
Pd1 2_655 Pd1 . N14 . 100.05(7) yes
O2 . Pd1 . N14 . 173.08(9) yes
C6 . Pd1 . N14 . 94.52(11) yes
Pd1 2_655 Pd1 . N17 . 108.86(7) yes
O2 . Pd1 . N17 . 87.12(9) yes
C6 . Pd1 . N17 . 177.97(10) yes
N14 . Pd1 . N17 . 86.06(10) yes
Pd1 . O2 . C3 . 128.70(19) yes
O2 . C3 . N4 . 124.3(3) yes
O2 . C3 . C13 . 118.0(3) yes
N4 . C3 . C13 . 117.7(3) yes
C3 . N4 . C5 . 128.5(2) yes
C3 . N4 . H41 . 116.5 no
C5 . N4 . H41 . 115.0 no
N4 . C5 . C6 . 124.4(3) yes
N4 . C5 . C11 . 113.5(2) yes
C6 . C5 . C11 . 122.1(3) yes
C5 . C6 . Pd1 . 121.9(2) yes
C5 . C6 . C7 . 116.5(3) yes
Pd1 . C6 . C7 . 121.6(2) yes
C6 . C7 . C8 . 121.1(3) yes
C6 . C7 . H71 . 121.4 no
C8 . C7 . H71 . 117.5 no
C7 . C8 . F9 . 120.7(3) yes
C7 . C8 . C10 . 120.8(3) yes
F9 . C8 . C10 . 118.5(3) yes
C8 . C10 . C11 . 120.4(3) yes
C8 . C10 . F12 . 119.7(3) yes
C11 . C10 . F12 . 119.9(3) yes
C5 . C11 . C10 . 119.0(3) yes
C5 . C11 . H111 . 120.4 no
C10 . C11 . H111 . 120.5 no
C3 . C13 . H131 . 110.5 no
C3 . C13 . H132 . 111.0 no
H131 . C13 . H132 . 108.6 no
C3 . C13 . H133 . 108.1 no
H131 . C13 . H133 . 108.6 no
H132 . C13 . H133 . 110.1 no
Pd1 . N14 . C15 . 167.9(2) yes
N14 . C15 . C16 . 179.1(3) yes
C15 . C16 . H163 . 110.4 no
C15 . C16 . H162 . 109.0 no
H163 . C16 . H162 . 110.2 no
C15 . C16 . H161 . 108.4 no
H163 . C16 . H161 . 109.1 no
H162 . C16 . H161 . 109.6 no
Pd1 . N17 . C18 . 173.0(3) yes
N17 . C18 . C19 . 179.3(3) yes
C18 . C19 . H191 . 109.3 no
C18 . C19 . H192 . 108.4 no
H191 . C19 . H192 . 110.0 no
C18 . C19 . H193 . 110.8 no
H191 . C19 . H193 . 109.3 no
H192 . C19 . H193 . 108.9 no
O21 . S20 . O22 . 114.80(14) yes
O21 . S20 . O23 . 112.02(14) yes
O22 . S20 . O23 . 111.09(13) yes
O21 . S20 . C24 . 106.94(13) yes
O22 . S20 . C24 . 107.15(14) yes
O23 . S20 . C24 . 104.05(13) yes
S20 . C24 . C25 . 119.7(2) yes
S20 . C24 . C29 . 120.9(2) yes
C25 . C24 . C29 . 119.4(3) yes
C24 . C25 . C26 . 119.9(3) yes
C24 . C25 . H251 . 120.5 no
C26 . C25 . H251 . 119.6 no
C25 . C26 . C27 . 121.2(3) yes
C25 . C26 . H261 . 119.7 no
C27 . C26 . H261 . 119.0 no
C26 . C27 . C28 . 118.1(3) yes
C26 . C27 . C30 . 120.7(3) yes
C28 . C27 . C30 . 121.2(3) yes
C27 . C28 . C29 . 121.6(3) yes
C27 . C28 . H281 . 119.0 no
C29 . C28 . H281 . 119.3 no
C28 . C29 . C24 . 119.8(3) yes
C28 . C29 . H291 . 120.4 no
C24 . C29 . H291 . 119.8 no
C27 . C30 . H301 . 110.3 no
C27 . C30 . H302 . 111.5 no
H301 . C30 . H302 . 107.6 no
C27 . C30 . H303 . 110.5 no
H301 . C30 . H303 . 109.2 no
H302 . C30 . H303 . 107.6 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Pd1 . Pd1 2_655 3.4636(4) yes
Pd1 . O2 . 1.999(2) yes
Pd1 . C6 . 1.980(3) yes
Pd1 . N14 . 2.008(3) yes
Pd1 . N17 . 2.130(3) yes
O2 . C3 . 1.256(3) yes
C3 . N4 . 1.322(4) yes
C3 . C13 . 1.496(4) yes
N4 . C5 . 1.417(4) yes
N4 . H41 . 0.855 no
C5 . C6 . 1.399(4) yes
C5 . C11 . 1.401(4) yes
C6 . C7 . 1.407(4) yes
C7 . C8 . 1.371(4) yes
C7 . H71 . 0.949 no
C8 . F9 . 1.360(3) yes
C8 . C10 . 1.380(4) yes
C10 . C11 . 1.365(4) yes
C10 . F12 . 1.359(3) yes
C11 . H111 . 0.952 no
C13 . H131 . 0.962 no
C13 . H132 . 0.962 no
C13 . H133 . 0.961 no
N14 . C15 . 1.138(4) yes
C15 . C16 . 1.452(4) yes
C16 . H163 . 0.954 no
C16 . H162 . 0.949 no
C16 . H161 . 0.943 no
N17 . C18 . 1.138(4) yes
C18 . C19 . 1.460(4) yes
C19 . H191 . 0.954 no
C19 . H192 . 0.960 no
C19 . H193 . 0.954 no
S20 . O21 . 1.449(2) yes
S20 . O22 . 1.454(2) yes
S20 . O23 . 1.480(2) yes
S20 . C24 . 1.775(3) yes
C24 . C25 . 1.398(4) yes
C24 . C29 . 1.382(4) yes
C25 . C26 . 1.382(4) yes
C25 . H251 . 0.932 no
C26 . C27 . 1.390(5) yes
C26 . H261 . 0.941 no
C27 . C28 . 1.384(5) yes
C27 . C30 . 1.502(4) yes
C28 . C29 . 1.387(4) yes
C28 . H281 . 0.939 no
C29 . H291 . 0.939 no
C30 . H301 . 0.958 no
C30 . H302 . 0.960 no
C30 . H303 . 0.952 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C11 . H111 . O22 . 136 0.95 2.44 3.194(5) yes
C13 . H131 . O23 . 143 0.96 2.51 3.332(5) yes
C16 . H163 . O21 2_655 142 0.95 2.55 3.349(5) yes
C16 . H161 . O23 2_555 141 0.94 2.49 3.270(5) yes
C29 . H291 . O21 2_666 131 0.94 2.59 3.275(5) yes
N4 . H41 . O23 . 174 0.85 1.91 2.758(5) yes
