#------------------------------------------------------------------------------
#$Date: 2016-03-25 13:15:42 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179834 $
#$URL: svn://www.crystallography.net/cod/cif/7/01/30/7013077.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_7013077
loop_
_publ_author_name
'Robin B. Bedford'
'Catherine S. J. Cazin'
'Simon J. Coles'
'Thomas Gelbrich'
'Michael B. Hursthouse'
'Véronique J. M. Scordia'
_publ_section_title
;
 Phosphine and arsine adducts of N-donor palladacycles as catalysts in
 the Suzuki coupling of aryl bromides
;
_journal_issue                   17
_journal_name_full               'Dalton Trans.'
_journal_page_first              3350
_journal_page_last               3356
_journal_paper_doi               10.1039/B304053D
_journal_year                    2003
_chemical_formula_sum            'C33 H25 F3 N O2 P Pd'
_chemical_formula_weight         661.91
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 104.20(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.911(2)
_cell_length_b                   29.932(6)
_cell_length_c                   9.907(2)
_cell_measurement_temperature    150(2)
_cell_volume                     2849.2(11)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.949
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0868
_diffrn_reflns_av_sigmaI/netI    0.0683
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            14475
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.94
_exptl_absorpt_coefficient_mu    0.759
_exptl_absorpt_correction_T_max  0.9850
_exptl_absorpt_correction_T_min  0.7029
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SORTAV (Blessing, 1997)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1336
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.074
_refine_diff_density_min         -1.297
_refine_diff_density_rms         0.102
_refine_ls_extinction_coef       0.0010(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     396
_refine_ls_number_reflns         5317
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0429
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0580P)²+1.7947P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1154
_refine_ls_wR_factor_ref         0.1188
_reflns_number_gt                4675
_reflns_number_total             5317
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            B304053D.txt
_cod_data_source_block           9d
_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_cell_volume        2849.3(10)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7013077
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
Pd1 Pd 0.20873(2) 0.164766(7) 0.43763(2) 0.01575(12) Uani 1 1 d . . .
P1 P 0.30991(9) 0.09713(3) 0.47456(8) 0.01532(19) Uani 1 1 d . . .
F1 F -0.1684(4) 0.15083(14) 0.0324(4) 0.1088(16) Uani 1 1 d . . .
F2 F -0.1242(4) 0.08435(12) 0.0787(3) 0.0879(12) Uani 1 1 d . . .
F3 F -0.0492(3) 0.11455(12) -0.0777(2) 0.0674(9) Uani 1 1 d . . .
O1 O 0.0432(2) 0.14077(8) 0.2749(2) 0.0217(5) Uani 1 1 d . . .
O2 O 0.1714(3) 0.13996(8) 0.1165(2) 0.0285(6) Uani 1 1 d . . .
N1 N 0.1287(3) 0.23084(9) 0.4154(3) 0.0198(6) Uani 1 1 d . . .
C1 C 0.1958(4) 0.25617(11) 0.5150(3) 0.0237(7) Uani 1 1 d . . .
H1 H 0.1686 0.2864 0.5214 0.025(9) Uiso 1 1 calc R . .
C2 C 0.3126(4) 0.23783(11) 0.6162(3) 0.0212(7) Uani 1 1 d . . .
C3 C 0.3478(3) 0.19305(11) 0.5957(3) 0.0201(7) Uani 1 1 d . . .
C4 C 0.4672(4) 0.17690(12) 0.6895(3) 0.0247(8) Uani 1 1 d . . .
H4 H 0.4984 0.1475 0.6779 0.025(9) Uiso 1 1 calc R . .
C5 C 0.5415(4) 0.20284(13) 0.7994(4) 0.0302(8) Uani 1 1 d . . .
H5 H 0.6225 0.1909 0.8608 0.027(10) Uiso 1 1 calc R . .
C6 C 0.4993(4) 0.24565(13) 0.8206(4) 0.0327(9) Uani 1 1 d . . .
H6 H 0.5481 0.2626 0.8985 0.028(10) Uiso 1 1 calc R . .
C7 C 0.3856(4) 0.26361(12) 0.7274(4) 0.0299(8) Uani 1 1 d . . .
H7 H 0.3571 0.2934 0.7390 0.025(9) Uiso 1 1 calc R . .
C8 C 0.0634(3) 0.13553(10) 0.1555(3) 0.0202(7) Uani 1 1 d . . .
C9 C -0.0685(4) 0.12206(12) 0.0462(3) 0.0275(8) Uani 1 1 d . . .
C10 C 0.0218(3) 0.25109(11) 0.3084(3) 0.0203(7) Uani 1 1 d . . .
C11 C -0.1054(4) 0.23011(12) 0.2613(3) 0.0245(7) Uani 1 1 d . . .
H11 H -0.1220 0.2019 0.2981 0.010(8) Uiso 1 1 calc R . .
C12 C -0.2077(4) 0.25044(13) 0.1607(4) 0.0311(8) Uani 1 1 d . . .
H12 H -0.2950 0.2360 0.1282 0.043(12) Uiso 1 1 calc R . .
C13 C -0.1850(4) 0.29186(13) 0.1059(4) 0.0333(9) Uani 1 1 d . . .
H13 H -0.2564 0.3059 0.0375 0.055(13) Uiso 1 1 calc R . .
C14 C -0.0569(4) 0.31214(13) 0.1529(4) 0.0332(9) Uani 1 1 d . . .
H14 H -0.0397 0.3402 0.1157 0.058(15) Uiso 1 1 calc R . .
C15 C 0.0460(4) 0.29200(12) 0.2531(4) 0.0267(8) Uani 1 1 d . . .
H15 H 0.1339 0.3062 0.2845 0.023(9) Uiso 1 1 calc R . .
C20 C 0.2102(3) 0.05365(11) 0.3648(3) 0.0178(7) Uani 1 1 d . . .
C21 C 0.2568(4) 0.03024(11) 0.2644(3) 0.0240(8) Uani 1 1 d . . .
H21 H 0.3453 0.0368 0.2482 0.038(11) Uiso 1 1 calc R . .
C22 C 0.1741(4) -0.00277(13) 0.1874(4) 0.0330(9) Uani 1 1 d . . .
H22 H 0.2066 -0.0188 0.1188 0.060(14) Uiso 1 1 calc R . .
C23 C 0.0446(4) -0.01263(13) 0.2097(4) 0.0321(9) Uani 1 1 d . . .
H23 H -0.0116 -0.0352 0.1563 0.035(11) Uiso 1 1 calc R . .
C24 C -0.0023(4) 0.01045(12) 0.3097(4) 0.0287(8) Uani 1 1 d . . .
H24 H -0.0909 0.0038 0.3254 0.026(9) Uiso 1 1 calc R . .
C25 C 0.0793(3) 0.04320(12) 0.3868(3) 0.0234(7) Uani 1 1 d . . .
H25 H 0.0465 0.0589 0.4557 0.025(9) Uiso 1 1 calc R . .
C30 C 0.4811(3) 0.09706(10) 0.4376(3) 0.0176(7) Uani 1 1 d . . .
C31 C 0.6019(3) 0.08133(11) 0.5292(3) 0.0222(7) Uani 1 1 d . . .
H31 H 0.5972 0.0682 0.6152 0.026(10) Uiso 1 1 calc R . .
C32 C 0.7294(4) 0.08485(12) 0.4945(4) 0.0268(8) Uani 1 1 d . . .
H32 H 0.8112 0.0738 0.5569 0.049(13) Uiso 1 1 calc R . .
C33 C 0.7383(4) 0.10431(12) 0.3700(4) 0.0299(8) Uani 1 1 d . . .
H33 H 0.8258 0.1069 0.3475 0.059(14) Uiso 1 1 calc R . .
C34 C 0.6189(4) 0.11984(12) 0.2792(4) 0.0278(8) Uani 1 1 d . . .
H34 H 0.6246 0.1331 0.1936 0.043(12) Uiso 1 1 calc R . .
C35 C 0.4898(4) 0.11628(11) 0.3116(3) 0.0235(7) Uani 1 1 d . . .
H35 H 0.4082 0.1269 0.2480 0.030(10) Uiso 1 1 calc R . .
C40 C 0.3274(3) 0.07203(11) 0.6453(3) 0.0173(7) Uani 1 1 d . . .
C41 C 0.2829(4) 0.09456(11) 0.7498(3) 0.0229(7) Uani 1 1 d . . .
H41 H 0.2459 0.1239 0.7329 0.021(9) Uiso 1 1 calc R . .
C42 C 0.2922(4) 0.07473(13) 0.8775(3) 0.0292(8) Uani 1 1 d . . .
H42 H 0.2627 0.0904 0.9486 0.026(10) Uiso 1 1 calc R . .
C43 C 0.3448(4) 0.03180(14) 0.9013(3) 0.0311(9) Uani 1 1 d . . .
H43 H 0.3521 0.0182 0.9894 0.021(9) Uiso 1 1 calc R . .
C44 C 0.3866(4) 0.00869(12) 0.7981(3) 0.0258(8) Uani 1 1 d . . .
H44 H 0.4220 -0.0208 0.8151 0.023(9) Uiso 1 1 calc R . .
C45 C 0.3768(3) 0.02852(11) 0.6695(3) 0.0214(7) Uani 1 1 d . . .
H45 H 0.4039 0.0124 0.5979 0.021(9) 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'
F F 0.0171 0.0103 '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'
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
C3 Pd1 N1 81.67(12) . . ?
C3 Pd1 O1 172.80(11) . . ?
N1 Pd1 O1 92.12(10) . . ?
C3 Pd1 P1 93.41(10) . . ?
N1 Pd1 P1 175.00(8) . . ?
O1 Pd1 P1 92.85(7) . . ?
C30 P1 C40 107.78(15) . . ?
C30 P1 C20 105.93(14) . . ?
C40 P1 C20 100.00(15) . . ?
C30 P1 Pd1 111.62(10) . . ?
C40 P1 Pd1 117.38(11) . . ?
C20 P1 Pd1 113.00(11) . . ?
C8 O1 Pd1 119.0(2) . . ?
C1 N1 C10 117.7(3) . . ?
C1 N1 Pd1 111.0(2) . . ?
C10 N1 Pd1 131.2(2) . . ?
N1 C1 C2 118.9(3) . . ?
N1 C1 H1 120.6 . . ?
C2 C1 H1 120.6 . . ?
C7 C2 C3 122.7(3) . . ?
C7 C2 C1 120.8(3) . . ?
C3 C2 C1 116.5(3) . . ?
C4 C3 C2 115.5(3) . . ?
C4 C3 Pd1 132.9(3) . . ?
C2 C3 Pd1 111.5(2) . . ?
C5 C4 C3 121.7(3) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 H4 119.1 . . ?
C6 C5 C4 121.0(3) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C7 119.2(3) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 H6 120.4 . . ?
C6 C7 C2 119.6(3) . . ?
C6 C7 H7 120.2 . . ?
C2 C7 H7 120.2 . . ?
O2 C8 O1 129.3(3) . . ?
O2 C8 C9 117.6(3) . . ?
O1 C8 C9 113.1(3) . . ?
F1 C9 F3 107.4(3) . . ?
F1 C9 F2 103.8(4) . . ?
F3 C9 F2 104.2(3) . . ?
F1 C9 C8 113.4(3) . . ?
F3 C9 C8 114.4(3) . . ?
F2 C9 C8 112.6(3) . . ?
C15 C10 C11 120.0(3) . . ?
C15 C10 N1 119.8(3) . . ?
C11 C10 N1 120.2(3) . . ?
C12 C11 C10 119.5(3) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C11 C12 C13 121.0(4) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C14 C13 C12 118.9(4) . . ?
C14 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?
C15 C14 C13 120.6(4) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C10 120.2(4) . . ?
C14 C15 H15 119.9 . . ?
C10 C15 H15 119.9 . . ?
C21 C20 C25 118.8(3) . . ?
C21 C20 P1 124.2(3) . . ?
C25 C20 P1 117.0(2) . . ?
C20 C21 C22 120.0(3) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C23 C22 C21 120.6(3) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C24 C23 C22 119.8(3) . . ?
C24 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C23 C24 C25 120.0(3) . . ?
C23 C24 H24 120.0 . . ?
C25 C24 H24 120.0 . . ?
C24 C25 C20 120.9(3) . . ?
C24 C25 H25 119.6 . . ?
C20 C25 H25 119.6 . . ?
C35 C30 C31 119.3(3) . . ?
C35 C30 P1 116.4(2) . . ?
C31 C30 P1 124.3(2) . . ?
C32 C31 C30 120.0(3) . . ?
C32 C31 H31 120.0 . . ?
C30 C31 H31 120.0 . . ?
C33 C32 C31 120.7(3) . . ?
C33 C32 H32 119.6 . . ?
C31 C32 H32 119.6 . . ?
C34 C33 C32 119.4(3) . . ?
C34 C33 H33 120.3 . . ?
C32 C33 H33 120.3 . . ?
C33 C34 C35 120.7(3) . . ?
C33 C34 H34 119.6 . . ?
C35 C34 H34 119.6 . . ?
C30 C35 C34 119.9(3) . . ?
C30 C35 H35 120.1 . . ?
C34 C35 H35 120.1 . . ?
C45 C40 C41 119.1(3) . . ?
C45 C40 P1 119.7(2) . . ?
C41 C40 P1 121.0(2) . . ?
C42 C41 C40 120.7(3) . . ?
C42 C41 H41 119.6 . . ?
C40 C41 H41 119.6 . . ?
C41 C42 C43 119.5(3) . . ?
C41 C42 H42 120.2 . . ?
C43 C42 H42 120.2 . . ?
C44 C43 C42 120.5(3) . . ?
C44 C43 H43 119.7 . . ?
C42 C43 H43 119.7 . . ?
C43 C44 C45 120.0(3) . . ?
C43 C44 H44 120.0 . . ?
C45 C44 H44 120.0 . . ?
C44 C45 C40 120.1(3) . . ?
C44 C45 H45 120.0 . . ?
C40 C45 H45 120.0 . . ?
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
Pd1 C3 2.003(3) . ?
Pd1 N1 2.122(3) . ?
Pd1 O1 2.124(2) . ?
Pd1 P1 2.2489(9) . ?
P1 C30 1.821(3) . ?
P1 C40 1.820(3) . ?
P1 C20 1.823(3) . ?
F1 C9 1.294(5) . ?
F2 C9 1.330(5) . ?
F3 C9 1.308(4) . ?
O1 C8 1.257(4) . ?
O2 C8 1.232(4) . ?
N1 C1 1.292(4) . ?
N1 C10 1.436(4) . ?
C1 C2 1.441(5) . ?
C1 H1 0.9500 . ?
C2 C7 1.393(5) . ?
C2 C3 1.412(5) . ?
C3 C4 1.399(5) . ?
C4 C5 1.392(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.380(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.380(5) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.533(5) . ?
C10 C15 1.386(5) . ?
C10 C11 1.383(5) . ?
C11 C12 1.377(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.394(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.381(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.375(5) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C20 C21 1.386(4) . ?
C20 C25 1.403(4) . ?
C21 C22 1.386(5) . ?
C21 H21 0.9500 . ?
C22 C23 1.387(5) . ?
C22 H22 0.9500 . ?
C23 C24 1.379(5) . ?
C23 H23 0.9500 . ?
C24 C25 1.377(5) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C30 C35 1.396(4) . ?
C30 C31 1.395(5) . ?
C31 C32 1.392(5) . ?
C31 H31 0.9500 . ?
C32 C33 1.386(5) . ?
C32 H32 0.9500 . ?
C33 C34 1.380(5) . ?
C33 H33 0.9500 . ?
C34 C35 1.398(5) . ?
C34 H34 0.9500 . ?
C35 H35 0.9500 . ?
C40 C45 1.391(5) . ?
C40 C41 1.395(4) . ?
C41 C42 1.380(5) . ?
C41 H41 0.9500 . ?
C42 C43 1.385(5) . ?
C42 H42 0.9500 . ?
C43 C44 1.379(5) . ?
C43 H43 0.9500 . ?
C44 C45 1.388(5) . ?
C44 H44 0.9500 . ?
C45 H45 0.9500 . ?
