#------------------------------------------------------------------------------
#$Date: 2016-03-21 06:59:19 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178543 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/49/4064968.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_4064968
loop_
_publ_author_name
'Vicente, José'
'Saura-Llamas, Isabel'
'Oliva-Madrid, María-José'
'García-López, José-Antonio'
'Bautista, Delia'
_publ_section_title
;
 A New Method for High-Yield Cyclopalladation of Primary and Secondary
 Amines. Atom-Efficient Open-to-Air Inexpensive Synthesis of Buchwald-Type
 Precatalysts
;
_journal_issue                   17
_journal_name_full               Organometallics
_journal_page_first              4624
_journal_paper_doi               10.1021/om200464s
_journal_volume                  30
_journal_year                    2011
_chemical_absolute_configuration rmad
_chemical_formula_sum            'C37 H48 Cl3 I N O4 P Pd'
_chemical_formula_weight         941.38
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 100.862(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.9357(11)
_cell_length_b                   11.9801(12)
_cell_length_c                   13.0750(11)
_cell_measurement_reflns_used    7837
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.93
_cell_measurement_theta_min      2.32
_cell_volume                     1989.9(3)
_computing_cell_refinement       'Bruker SAINT'
_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      100(2)
_diffrn_detector_area_resol_mean 8.26
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       ω-scan
_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  0.0368
_diffrn_reflns_av_sigmaI/netI    0.0527
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            24605
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.71
_diffrn_reflns_theta_min         1.60
_exptl_absorpt_coefficient_mu    1.522
_exptl_absorpt_correction_T_max  0.8880
_exptl_absorpt_correction_T_min  0.7724
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_density_diffrn    1.571
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             948
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.535
_refine_diff_density_min         -1.026
_refine_diff_density_rms         0.117
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.009(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    'NH2 free, rigid methyls, others riding'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     434
_refine_ls_number_reflns         9421
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0422
_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)+(0.0386P)²+1.7729P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0900
_refine_ls_wR_factor_ref         0.0911
_reflns_number_gt                9000
_reflns_number_total             9421
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om200464s_si_001.cif
_cod_data_source_block           jod1382s
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               4064968
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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_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 0.29428(3) 0.55917(3) 0.18759(3) 0.01530(8) Uani 1 1 d . . .
I1 I 0.09954(2) 0.47884(2) 0.11113(2) 0.02054(8) Uani 1 1 d . . .
N1 N 0.3293(3) 0.3984(4) 0.2540(4) 0.0245(9) Uani 1 1 d D . .
H01A H 0.275(4) 0.358(5) 0.240(5) 0.029 Uiso 1 1 d D . .
H01B H 0.336(5) 0.410(5) 0.319(3) 0.029 Uiso 1 1 d D . .
P1 P 0.25950(9) 0.73059(10) 0.11238(9) 0.0143(2) Uani 1 1 d . . .
C1 C 0.4442(4) 0.5961(4) 0.2577(4) 0.0180(10) Uani 1 1 d . . .
C2 C 0.5208(4) 0.5166(4) 0.2438(4) 0.0178(10) Uani 1 1 d . . .
C3 C 0.6242(4) 0.5348(4) 0.2879(4) 0.0229(11) Uani 1 1 d . . .
H3 H 0.6756 0.4810 0.2785 0.027 Uiso 1 1 calc R . .
C4 C 0.6558(4) 0.6305(5) 0.3465(4) 0.0262(11) Uani 1 1 d . . .
H4 H 0.7280 0.6431 0.3747 0.031 Uiso 1 1 calc R . .
C5 C 0.5800(4) 0.7066(4) 0.3627(4) 0.0236(11) Uani 1 1 d . . .
H5 H 0.5993 0.7714 0.4037 0.028 Uiso 1 1 calc R . .
C6 C 0.4751(4) 0.6872(4) 0.3181(4) 0.0193(10) Uani 1 1 d . . .
H6 H 0.4232 0.7391 0.3303 0.023 Uiso 1 1 calc R . .
C7 C 0.4178(4) 0.3361(4) 0.2243(4) 0.0229(11) Uani 1 1 d . . .
H7 H 0.3884 0.2795 0.1703 0.027 Uiso 1 1 calc R . .
C8 C 0.4904(4) 0.4150(4) 0.1780(4) 0.0211(10) Uani 1 1 d . . .
H8A H 0.5549 0.3740 0.1702 0.025 Uiso 1 1 calc R . .
H8B H 0.4544 0.4387 0.1077 0.025 Uiso 1 1 calc R . .
C9 C 0.4764(4) 0.2748(4) 0.3204(5) 0.0242(12) Uani 1 1 d . . .
O1 O 0.4622(3) 0.2907(3) 0.4062(3) 0.0319(9) Uani 1 1 d . . .
C10 C 0.6058(4) 0.1412(5) 0.3805(5) 0.0385(14) Uani 1 1 d . . .
H10A H 0.6486 0.1925 0.4294 0.058 Uiso 1 1 calc R . .
H10B H 0.6519 0.0880 0.3539 0.058 Uiso 1 1 calc R . .
H10C H 0.5573 0.1005 0.4163 0.058 Uiso 1 1 calc R . .
O2 O 0.5465(3) 0.2034(3) 0.2952(3) 0.0297(8) Uani 1 1 d . . .
C11 C 0.1977(3) 0.7189(4) -0.0268(3) 0.0143(9) Uani 1 1 d . . .
H11 H 0.1243 0.6917 -0.0289 0.017 Uiso 1 1 calc R . .
C13 C 0.1896(4) 0.6207(4) -0.1979(4) 0.0229(11) Uani 1 1 d . . .
H13A H 0.1177 0.5934 -0.1965 0.027 Uiso 1 1 calc R . .
H13B H 0.2250 0.5651 -0.2354 0.027 Uiso 1 1 calc R . .
C12 C 0.2508(4) 0.6334(4) -0.0864(4) 0.0216(10) Uani 1 1 d . . .
H12A H 0.2543 0.5605 -0.0504 0.026 Uiso 1 1 calc R . .
H12B H 0.3236 0.6577 -0.0879 0.026 Uiso 1 1 calc R . .
C14 C 0.1832(4) 0.7326(4) -0.2552(4) 0.0223(10) Uani 1 1 d . . .
H14A H 0.2548 0.7579 -0.2603 0.027 Uiso 1 1 calc R . .
H14B H 0.1421 0.7236 -0.3267 0.027 Uiso 1 1 calc R . .
C15 C 0.1308(4) 0.8191(4) -0.1969(4) 0.0209(10) Uani 1 1 d . . .
H15A H 0.0569 0.7968 -0.1978 0.025 Uiso 1 1 calc R . .
H15B H 0.1299 0.8920 -0.2328 0.025 Uiso 1 1 calc R . .
C16 C 0.1881(4) 0.8321(4) -0.0837(4) 0.0176(10) Uani 1 1 d . . .
H16A H 0.1490 0.8850 -0.0470 0.021 Uiso 1 1 calc R . .
H16B H 0.2593 0.8631 -0.0824 0.021 Uiso 1 1 calc R . .
C21 C 0.1654(3) 0.8100(4) 0.1751(4) 0.0162(9) Uani 1 1 d . . .
H21 H 0.1832 0.8909 0.1715 0.019 Uiso 1 1 calc R . .
C22 C 0.0490(4) 0.7960(4) 0.1230(4) 0.0199(10) Uani 1 1 d . . .
H22A H 0.0392 0.8190 0.0491 0.024 Uiso 1 1 calc R . .
H22B H 0.0286 0.7165 0.1253 0.024 Uiso 1 1 calc R . .
C23 C -0.0209(4) 0.8668(4) 0.1790(4) 0.0243(11) Uani 1 1 d . . .
H23A H -0.0952 0.8577 0.1441 0.029 Uiso 1 1 calc R . .
H23B H -0.0019 0.9464 0.1743 0.029 Uiso 1 1 calc R . .
C24 C -0.0093(4) 0.8340(5) 0.2933(4) 0.0317(13) Uani 1 1 d . . .
H24A H -0.0537 0.8832 0.3279 0.038 Uiso 1 1 calc R . .
H24B H -0.0336 0.7561 0.2985 0.038 Uiso 1 1 calc R . .
C25 C 0.1047(4) 0.8440(5) 0.3474(4) 0.0314(12) Uani 1 1 d . . .
H25A H 0.1121 0.8158 0.4196 0.038 Uiso 1 1 calc R . .
H25B H 0.1253 0.9237 0.3510 0.038 Uiso 1 1 calc R . .
C26 C 0.1796(4) 0.7783(5) 0.2907(4) 0.0252(11) Uani 1 1 d . . .
H26A H 0.2533 0.7932 0.3250 0.030 Uiso 1 1 calc R . .
H26B H 0.1663 0.6974 0.2966 0.030 Uiso 1 1 calc R . .
C31 C 0.3794(3) 0.8130(4) 0.1088(3) 0.0140(9) Uani 1 1 d . . .
C32 C 0.4026(4) 0.9275(4) 0.1306(3) 0.0147(9) Uani 1 1 d . . .
C33 C 0.5033(4) 0.9649(4) 0.1277(4) 0.0182(9) Uani 1 1 d . . .
H33 H 0.5202 1.0405 0.1454 0.022 Uiso 1 1 calc R . .
C34 C 0.5802(4) 0.8977(5) 0.1002(4) 0.0225(11) Uani 1 1 d . . .
H34 H 0.6484 0.9267 0.0994 0.027 Uiso 1 1 calc R . .
C35 C 0.5570(4) 0.7878(4) 0.0740(4) 0.0184(10) Uani 1 1 d . . .
H35 H 0.6083 0.7408 0.0530 0.022 Uiso 1 1 calc R . .
C36 C 0.4581(4) 0.7468(4) 0.0786(3) 0.0158(9) Uani 1 1 d . . .
H36 H 0.4428 0.6709 0.0608 0.019 Uiso 1 1 calc R . .
C41 C 0.3272(4) 1.0100(3) 0.1606(4) 0.0163(9) Uani 1 1 d . . .
C42 C 0.3224(4) 1.0273(4) 0.2666(4) 0.0212(10) Uani 1 1 d . . .
C43 C 0.2513(5) 1.1025(4) 0.2960(5) 0.0282(12) Uani 1 1 d . . .
H43 H 0.2490 1.1140 0.3674 0.034 Uiso 1 1 calc R . .
C44 C 0.1844(4) 1.1601(4) 0.2193(5) 0.0272(12) Uani 1 1 d . . .
H44 H 0.1333 1.2084 0.2391 0.033 Uiso 1 1 calc R . .
C45 C 0.1886(4) 1.1503(4) 0.1154(4) 0.0246(11) Uani 1 1 d . . .
H45 H 0.1425 1.1921 0.0643 0.030 Uiso 1 1 calc R . .
C46 C 0.2636(4) 1.0763(4) 0.0866(4) 0.0177(9) Uani 1 1 d . . .
C47 C 0.3863(5) 0.9737(6) 0.4435(4) 0.0366(12) Uani 1 1 d . . .
H47A H 0.4071 1.0494 0.4675 0.055 Uiso 1 1 calc R . .
H47B H 0.4343 0.9195 0.4836 0.055 Uiso 1 1 calc R . .
H47C H 0.3143 0.9592 0.4535 0.055 Uiso 1 1 calc R . .
O3 O 0.3908(3) 0.9637(3) 0.3345(3) 0.0274(8) Uani 1 1 d . . .
C48 C 0.2056(4) 1.1179(4) -0.0935(4) 0.0232(11) Uani 1 1 d . . .
H48A H 0.1348 1.0890 -0.0930 0.035 Uiso 1 1 calc R . .
H48B H 0.2245 1.1026 -0.1613 0.035 Uiso 1 1 calc R . .
H48C H 0.2068 1.1986 -0.0813 0.035 Uiso 1 1 calc R . .
O4 O 0.2789(2) 1.0649(3) -0.0139(2) 0.0188(6) Uiso 1 1 d . . .
C99 C 0.9081(8) 0.9448(9) 0.5915(14) 0.055(5) Uiso 0.600(10) 1 d PDU A 1
H99 H 0.9166 0.9517 0.6689 0.066 Uiso 0.600(10) 1 calc PR A 1
Cl1 Cl 0.9187(7) 0.8138(8) 0.5630(8) 0.142(4) Uiso 0.600(10) 1 d PDU A 1
Cl2 Cl 0.7860(3) 0.9902(4) 0.5372(3) 0.0695(14) Uiso 0.600(10) 1 d PDU A 1
Cl3 Cl 1.0023(5) 1.0246(4) 0.5516(4) 0.0771(14) Uiso 0.600(10) 1 d PDU A 1
C99' C 0.9341(17) 0.9612(19) 0.5981(19) 0.048(5) Uiso 0.400(10) 1 d PU A 2
H99' H 0.9356 0.9687 0.6746 0.058 Uiso 0.400(10) 1 calc PR A 2
Cl1' Cl 0.9280(3) 0.8058(3) 0.5618(3) 0.0200(11) Uiso 0.400(10) 1 d PU A 2
Cl2' Cl 0.8250(8) 1.0408(9) 0.5279(6) 0.100(3) Uiso 0.400(10) 1 d PU A 2
Cl3' Cl 1.0476(6) 1.0193(4) 0.5689(5) 0.0531(17) Uiso 0.400(10) 1 d PU A 2
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'
Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
C1 Pd1 N1 84.32(17)
C1 Pd1 P1 95.29(13)
N1 Pd1 P1 178.27(14)
C1 Pd1 I1 170.84(13)
N1 Pd1 I1 86.60(12)
P1 Pd1 I1 93.82(3)
C7 N1 Pd1 117.8(3)
C31 P1 C11 103.0(2)
C31 P1 C21 111.2(2)
C11 P1 C21 106.0(2)
C31 P1 Pd1 113.17(15)
C11 P1 Pd1 111.64(14)
C21 P1 Pd1 111.30(16)
C6 C1 C2 118.7(5)
C6 C1 Pd1 125.9(4)
C2 C1 Pd1 115.4(3)
C3 C2 C1 119.5(4)
C3 C2 C8 120.0(4)
C1 C2 C8 120.5(4)
C2 C3 C4 121.5(5)
C5 C4 C3 118.9(5)
C4 C5 C6 119.2(5)
C1 C6 C5 122.2(5)
N1 C7 C9 108.3(4)
N1 C7 C8 110.8(4)
C9 C7 C8 112.0(4)
C2 C8 C7 112.8(4)
O1 C9 O2 124.9(5)
O1 C9 C7 124.0(5)
O2 C9 C7 111.1(5)
C9 O2 C10 115.4(5)
C12 C11 C16 110.3(4)
C12 C11 P1 113.7(3)
C16 C11 P1 112.9(3)
C12 C13 C14 110.5(4)
C11 C12 C13 110.6(4)
C15 C14 C13 109.9(4)
C14 C15 C16 111.9(4)
C15 C16 C11 111.0(4)
C26 C21 C22 109.5(4)
C26 C21 P1 110.0(3)
C22 C21 P1 114.7(3)
C23 C22 C21 110.2(4)
C22 C23 C24 111.7(4)
C25 C24 C23 110.1(4)
C24 C25 C26 112.3(5)
C21 C26 C25 112.2(4)
C36 C31 C32 117.6(4)
C36 C31 P1 111.2(3)
C32 C31 P1 131.1(3)
C33 C32 C31 118.1(4)
C33 C32 C41 117.2(4)
C31 C32 C41 124.6(4)
C34 C33 C32 123.1(4)
C33 C34 C35 119.2(4)
C34 C35 C36 119.3(4)
C35 C36 C31 122.5(4)
C46 C41 C42 117.9(4)
C46 C41 C32 121.6(4)
C42 C41 C32 120.4(4)
O3 C42 C43 124.3(5)
O3 C42 C41 114.5(4)
C43 C42 C41 121.2(5)
C44 C43 C42 118.7(5)
C45 C44 C43 122.6(5)
C44 C45 C46 118.2(5)
O4 C46 C41 115.8(4)
O4 C46 C45 123.1(4)
C41 C46 C45 121.0(4)
C42 O3 C47 117.1(4)
C46 O4 C48 117.4(4)
Cl1 C99 Cl2 109.0(9)
Cl1 C99 Cl3 112.0(9)
Cl2 C99 Cl3 110.8(8)
Cl3' C99' Cl2' 106.8(13)
Cl3' C99' Cl1' 109.4(11)
Cl2' C99' Cl1' 113.3(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Pd1 C1 2.032(5)
Pd1 N1 2.126(4)
Pd1 P1 2.2848(12)
Pd1 I1 2.7060(5)
N1 C7 1.479(7)
P1 C31 1.846(5)
P1 C11 1.849(5)
P1 C21 1.854(5)
C1 C6 1.362(7)
C1 C2 1.410(7)
C2 C3 1.372(7)
C2 C8 1.500(7)
C3 C4 1.396(8)
C4 C5 1.385(8)
C5 C6 1.392(7)
C7 C9 1.528(7)
C7 C8 1.535(7)
C9 O1 1.186(7)
C9 O2 1.333(7)
C10 O2 1.437(6)
C11 C12 1.526(6)
C11 C16 1.540(6)
C13 C12 1.529(7)
C13 C14 1.530(7)
C14 C15 1.520(7)
C15 C16 1.534(7)
C21 C26 1.535(7)
C21 C22 1.540(6)
C22 C23 1.523(7)
C23 C24 1.526(8)
C24 C25 1.516(8)
C25 C26 1.542(7)
C31 C36 1.405(6)
C31 C32 1.422(6)
C32 C33 1.385(6)
C32 C41 1.493(6)
C33 C34 1.379(7)
C34 C35 1.379(7)
C35 C36 1.381(6)
C41 C46 1.395(6)
C41 C42 1.413(7)
C42 O3 1.363(6)
C42 C43 1.392(7)
C43 C44 1.379(8)
C44 C45 1.376(8)
C45 C46 1.416(7)
C46 O4 1.372(6)
C47 O3 1.442(6)
C48 O4 1.419(6)
C99 Cl1 1.625(12)
C99 Cl2 1.694(12)
C99 Cl3 1.706(12)
C99' Cl3' 1.73(2)
C99' Cl2' 1.80(2)
C99' Cl1' 1.92(2)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C22 H22B I1 0.99 3.01 3.863(5) 145.3 .
C47 H47B O1 0.98 2.35 3.325(8) 173.7 2_656
