#------------------------------------------------------------------------------
#$Date: 2016-03-21 07:50:34 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178584 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/95/4069582.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_4069582
loop_
_publ_author_name
'Vicente, José'
'Saura-Llamas, Isabel'
'Turpín, Juana'
'Bautista, Delia'
'de Arellano, Carmen Ramírez'
'Jones, Peter G.'
_publ_section_title
;
 Insertion of One, Two, and Three Molecules of Alkyne into the Pd−C
 Bond of Ortho-palladated Primary and Secondary Arylalkylamines
;
_journal_issue                   14
_journal_name_full               Organometallics
_journal_page_first              4175
_journal_paper_doi               10.1021/om9002895
_journal_volume                  28
_journal_year                    2009
_chemical_formula_sum            'C30 H33 Br N2 O2 Pd'
_chemical_formula_weight         639.89
_chemical_name_systematic
; 
 ? 
;
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                89.506(2)
_cell_angle_beta                 78.929(2)
_cell_angle_gamma                70.892(2)
_cell_formula_units_Z            2
_cell_length_a                   9.2820(4)
_cell_length_b                   11.3665(5)
_cell_length_c                   14.9421(7)
_cell_measurement_reflns_used    6679
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.05
_cell_measurement_theta_min      2.29
_cell_volume                     1459.37(11)
_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      173(2)
_diffrn_detector_area_resol_mean 8.26
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.908
_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  0.0245
_diffrn_reflns_av_sigmaI/netI    0.0344
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            17030
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.24
_diffrn_reflns_theta_min         1.90
_exptl_absorpt_coefficient_mu    2.032
_exptl_absorpt_correction_T_max  0.7925
_exptl_absorpt_correction_T_min  0.7503
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.529
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    'NH free, rigid methyls others riding'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     332
_refine_ls_number_reflns         6555
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0296
_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)+(0.0346P)²+0.4178P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0683
_refine_ls_wR_factor_ref         0.0709
_reflns_number_gt                5778
_reflns_number_total             6555
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om9002895_si_002.cif
_cod_data_source_block           ja43bs
_cod_database_code               4069582
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_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 -0.050623(19) 0.683630(15) 0.330773(11) 0.01848(6) Uani 1 1 d . . .
Br1 Br -0.19521(3) 0.64034(2) 0.480876(15) 0.02669(7) Uani 1 1 d . . .
N1 N 0.0740(2) 0.49209(18) 0.31512(14) 0.0200(4) Uani 1 1 d . . .
H01 H 0.074(3) 0.475(2) 0.3645(15) 0.005(6) Uiso 1 1 d . . .
N2 N -0.2524(2) 0.96041(19) 0.34800(15) 0.0305(5) Uani 1 1 d . . .
C1 C 0.3239(3) 0.5355(2) 0.28969(15) 0.0216(5) Uani 1 1 d . . .
C2 C 0.3146(3) 0.6481(2) 0.24780(15) 0.0207(5) Uani 1 1 d . . .
C3 C 0.4106(3) 0.7138(2) 0.26549(17) 0.0264(5) Uani 1 1 d . . .
H3 H 0.4096 0.7874 0.2346 0.032 Uiso 1 1 calc R . .
C4 C 0.5073(3) 0.6729(2) 0.32744(18) 0.0308(6) Uani 1 1 d . . .
H4 H 0.5712 0.7190 0.3394 0.037 Uiso 1 1 calc R . .
C5 C 0.5109(3) 0.5655(3) 0.37186(17) 0.0310(6) Uani 1 1 d . . .
H5 H 0.5749 0.5386 0.4157 0.037 Uiso 1 1 calc R . .
C6 C 0.4213(3) 0.4972(2) 0.35230(16) 0.0260(5) Uani 1 1 d . . .
H6 H 0.4260 0.4224 0.3822 0.031 Uiso 1 1 calc R . .
C7 C 0.2375(3) 0.4537(2) 0.26412(16) 0.0229(5) Uani 1 1 d . . .
H7A H 0.2382 0.4569 0.1978 0.027 Uiso 1 1 calc R . .
H7B H 0.2920 0.3664 0.2765 0.027 Uiso 1 1 calc R . .
C8 C -0.0176(3) 0.4234(2) 0.27918(17) 0.0251(5) Uani 1 1 d . . .
H8A H -0.0114 0.4363 0.2131 0.030 Uiso 1 1 calc R . .
H8B H -0.1282 0.4602 0.3099 0.030 Uiso 1 1 calc R . .
C9 C 0.2055(3) 0.6951(2) 0.18400(15) 0.0218(5) Uani 1 1 d . A .
C10 C 0.0534(3) 0.7151(2) 0.20552(15) 0.0206(5) Uani 1 1 d . . .
C11 C -0.1723(3) 0.8590(2) 0.34330(16) 0.0262(5) Uani 1 1 d . . .
C12 C -0.3651(3) 1.0871(2) 0.35266(19) 0.0322(6) Uani 1 1 d . . .
C13 C -0.3010(3) 1.1555(2) 0.2753(2) 0.0391(7) Uani 1 1 d . . .
H13A H -0.2000 1.1586 0.2834 0.059 Uiso 1 1 calc R . .
H13B H -0.3736 1.2406 0.2760 0.059 Uiso 1 1 calc R . .
H13C H -0.2882 1.1114 0.2168 0.059 Uiso 1 1 calc R . .
C14 C -0.5173(3) 1.0732(3) 0.3404(3) 0.0559(9) Uani 1 1 d . . .
H14A H -0.5016 1.0288 0.2815 0.084 Uiso 1 1 calc R . .
H14B H -0.5957 1.1560 0.3419 0.084 Uiso 1 1 calc R . .
H14C H -0.5531 1.0260 0.3898 0.084 Uiso 1 1 calc R . .
C15 C -0.3784(4) 1.1477(3) 0.4458(2) 0.0481(8) Uani 1 1 d . . .
H15A H -0.4099 1.0968 0.4939 0.072 Uiso 1 1 calc R . .
H15B H -0.4565 1.2313 0.4525 0.072 Uiso 1 1 calc R . .
H15C H -0.2775 1.1541 0.4509 0.072 Uiso 1 1 calc R . .
C16 C 0.2824(3) 0.7158(2) 0.08987(16) 0.0262(5) Uani 1 1 d . . .
O1 O 0.3411(2) 0.79507(19) 0.07050(13) 0.0416(5) Uani 1 1 d . A .
O2 O 0.2648(6) 0.6430(5) 0.0281(2) 0.0255(10) Uiso 0.596(16) 1 d P A 1
C17 C 0.3244(9) 0.6602(7) -0.0666(4) 0.0391(15) Uiso 0.596(16) 1 d P A 1
H17A H 0.4362 0.6511 -0.0761 0.047 Uiso 0.596(16) 1 calc PR A 1
H17B H 0.2667 0.7441 -0.0842 0.047 Uiso 0.596(16) 1 calc PR A 1
C18 C 0.3015(9) 0.5619(7) -0.1215(4) 0.0419(16) Uiso 0.596(16) 1 d P A 1
H18A H 0.3568 0.4797 -0.1020 0.050 Uiso 0.596(16) 1 calc PR A 1
H18B H 0.3425 0.5677 -0.1863 0.050 Uiso 0.596(16) 1 calc PR A 1
H18C H 0.1902 0.5735 -0.1125 0.050 Uiso 0.596(16) 1 calc PR A 1
O2' O 0.3039(11) 0.6129(8) 0.0320(4) 0.0345(17) Uiso 0.404(16) 1 d P A 2
C17' C 0.3699(13) 0.6205(11) -0.0637(6) 0.041(2) Uiso 0.404(16) 1 d P A 2
H17C H 0.4713 0.5531 -0.0823 0.049 Uiso 0.404(16) 1 calc PR A 2
H17D H 0.3867 0.7017 -0.0733 0.049 Uiso 0.404(16) 1 calc PR A 2
C18' C 0.2527(14) 0.6066(13) -0.1215(6) 0.048(3) Uiso 0.404(16) 1 d P A 2
H18D H 0.2335 0.5276 -0.1095 0.057 Uiso 0.404(16) 1 calc PR A 2
H18E H 0.2963 0.6075 -0.1866 0.057 Uiso 0.404(16) 1 calc PR A 2
H18F H 0.1545 0.6760 -0.1047 0.057 Uiso 0.404(16) 1 calc PR A 2
C21 C 0.0349(3) 0.2851(2) 0.29202(18) 0.0278(5) Uani 1 1 d . . .
C22 C 0.1114(3) 0.1984(3) 0.2187(2) 0.0378(6) Uani 1 1 d . . .
H22 H 0.1338 0.2261 0.1592 0.045 Uiso 1 1 calc R . .
C23 C 0.1552(4) 0.0713(3) 0.2322(3) 0.0509(9) Uani 1 1 d . . .
H23 H 0.2063 0.0125 0.1818 0.061 Uiso 1 1 calc R . .
C24 C 0.1244(4) 0.0309(3) 0.3184(3) 0.0539(9) Uani 1 1 d . . .
H24 H 0.1536 -0.0560 0.3273 0.065 Uiso 1 1 calc R . .
C25 C 0.0517(4) 0.1152(3) 0.3919(3) 0.0487(8) Uani 1 1 d . . .
H25 H 0.0332 0.0868 0.4516 0.058 Uiso 1 1 calc R . .
C26 C 0.0052(3) 0.2424(2) 0.3784(2) 0.0343(6) Uani 1 1 d . . .
H26 H -0.0474 0.3005 0.4290 0.041 Uiso 1 1 calc R . .
C31 C -0.0559(3) 0.7697(2) 0.14334(16) 0.0252(5) Uani 1 1 d . . .
C32 C -0.0596(3) 0.8810(2) 0.10305(18) 0.0330(6) Uani 1 1 d . . .
H32 H 0.0128 0.9202 0.1124 0.040 Uiso 1 1 calc R . .
C33 C -0.1675(3) 0.9356(3) 0.04943(19) 0.0426(7) Uani 1 1 d . . .
H33 H -0.1679 1.0115 0.0222 0.051 Uiso 1 1 calc R . .
C34 C -0.2739(3) 0.8808(3) 0.0354(2) 0.0481(8) Uani 1 1 d . . .
H34 H -0.3470 0.9181 -0.0018 0.058 Uiso 1 1 calc R . .
C35 C -0.2733(4) 0.7715(3) 0.0758(2) 0.0530(9) Uani 1 1 d . . .
H35 H -0.3466 0.7331 0.0666 0.064 Uiso 1 1 calc R . .
C36 C -0.1662(3) 0.7171(3) 0.1299(2) 0.0415(7) Uani 1 1 d . . .
H36 H -0.1684 0.6424 0.1584 0.050 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'
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
C11 Pd1 C10 87.37(9)
C11 Pd1 N1 177.66(9)
C10 Pd1 N1 92.74(8)
C11 Pd1 Br1 92.78(7)
C10 Pd1 Br1 175.55(6)
N1 Pd1 Br1 86.94(6)
C7 N1 C8 111.99(18)
C7 N1 Pd1 117.07(14)
C8 N1 Pd1 110.21(14)
C11 N2 C12 175.4(2)
C6 C1 C2 118.7(2)
C6 C1 C7 120.2(2)
C2 C1 C7 121.0(2)
C3 C2 C1 119.1(2)
C3 C2 C9 120.8(2)
C1 C2 C9 120.1(2)
C4 C3 C2 120.8(2)
C5 C4 C3 120.0(2)
C6 C5 C4 119.7(2)
C5 C6 C1 121.5(2)
N1 C7 C1 112.48(18)
N1 C8 C21 114.83(19)
C10 C9 C2 124.3(2)
C10 C9 C16 121.3(2)
C2 C9 C16 114.35(19)
C9 C10 C31 123.8(2)
C9 C10 Pd1 121.76(17)
C31 C10 Pd1 114.27(16)
N2 C11 Pd1 174.9(2)
N2 C12 C14 106.8(2)
N2 C12 C13 107.1(2)
C14 C12 C13 111.6(2)
N2 C12 C15 107.2(2)
C14 C12 C15 112.3(3)
C13 C12 C15 111.6(2)
O1 C16 O2 122.8(3)
O1 C16 O2' 124.4(3)
O2 C16 O2' 17.6(3)
O1 C16 C9 125.9(2)
O2 C16 C9 111.0(2)
O2' C16 C9 108.4(3)
C16 O2 C17 116.4(3)
O2 C17 C18 105.9(4)
C16 O2' C17' 115.8(5)
O2' C17' C18' 107.7(6)
C26 C21 C22 118.7(2)
C26 C21 C8 119.7(2)
C22 C21 C8 121.6(2)
C23 C22 C21 120.4(3)
C24 C23 C22 119.9(3)
C23 C24 C25 120.5(3)
C24 C25 C26 119.7(3)
C21 C26 C25 120.8(3)
C36 C31 C32 117.7(2)
C36 C31 C10 121.2(2)
C32 C31 C10 120.9(2)
C33 C32 C31 120.9(3)
C34 C33 C32 120.5(3)
C33 C34 C35 119.3(3)
C34 C35 C36 120.2(3)
C35 C36 C31 121.2(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Pd1 C11 1.933(2)
Pd1 C10 2.021(2)
Pd1 N1 2.0950(19)
Pd1 Br1 2.5162(3)
N1 C7 1.484(3)
N1 C8 1.496(3)
N2 C11 1.143(3)
N2 C12 1.469(3)
C1 C6 1.393(3)
C1 C2 1.405(3)
C1 C7 1.505(3)
C2 C3 1.397(3)
C2 C9 1.492(3)
C3 C4 1.384(3)
C4 C5 1.379(4)
C5 C6 1.378(3)
C8 C21 1.508(3)
C9 C10 1.328(3)
C9 C16 1.504(3)
C10 C31 1.489(3)
C12 C14 1.516(4)
C12 C13 1.522(4)
C12 C15 1.524(4)
C16 O1 1.204(3)
C16 O2 1.313(4)
C16 O2' 1.398(7)
O2 C17 1.454(6)
C17 C18 1.485(8)
O2' C17' 1.458(10)
C17' C18' 1.559(14)
C21 C26 1.385(4)
C21 C22 1.392(4)
C22 C23 1.391(4)
C23 C24 1.373(5)
C24 C25 1.375(5)
C25 C26 1.391(4)
C31 C36 1.389(3)
C31 C32 1.390(3)
C32 C33 1.387(4)
C33 C34 1.375(4)
C34 C35 1.376(4)
C35 C36 1.386(4)
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
N1 H01 Br1 0.76(2) 2.88(2) 3.599(2) 158(2) 2_566
C15 H15B Br1 0.98 3.05 3.848(3) 140.0 2_476
