#------------------------------------------------------------------------------
#$Date: 2016-03-21 14:21:25 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178714 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/25/4082539.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_4082539
loop_
_publ_author_name
'Oliva-Madrid, María-José'
'García-López, José-Antonio'
'Saura-Llamas, Isabel'
'Bautista, Delia'
'Vicente, José'
_publ_section_title
;
 Reactivity toward Neutral N- and P-Donor Ligands of Eight-Membered
 Palladacycles Arising from Monoinsertion of Alkynes into the Pd--C Bond
 of Orthopalladated Homoveratrylamine and Phentermine. A New Example of
 the Transphobia Effect
;
_journal_issue                   1
_journal_name_full               Organometallics
_journal_page_first              33
_journal_paper_doi               10.1021/om401090b
_journal_volume                  33
_journal_year                    2014
_chemical_formula_sum            'C27 H33 Br N O2 P Pd'
_chemical_formula_weight         620.82
_chemical_name_systematic
; 
 ? 
;
_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                 92.022(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.1328(9)
_cell_length_b                   8.1803(7)
_cell_length_c                   31.117(3)
_cell_measurement_reflns_used    6772
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.68
_cell_measurement_theta_min      2.57
_cell_volume                     2577.7(4)
_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 1.000
_diffrn_measured_fraction_theta_max 0.945
_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  0.0293
_diffrn_reflns_av_sigmaI/netI    0.0246
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            30530
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.68
_diffrn_reflns_theta_min         2.09
_exptl_absorpt_coefficient_mu    2.356
_exptl_absorpt_correction_T_max  0.8913
_exptl_absorpt_correction_T_min  0.7175
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.600
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1256
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.586
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment
'NH2 free with SADI, rigid methyls, others riding'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         6278
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0285
_refine_ls_R_factor_gt           0.0247
_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)+(0.0263P)²+2.0375P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0564
_refine_ls_wR_factor_ref         0.0578
_reflns_number_gt                5731
_reflns_number_total             6278
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om401090b_si_002.cif
_cod_data_source_block           jod991s
_cod_original_sg_symbol_H-M      'P 2(1)/n'
_cod_database_code               4082539
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 0.216830(13) -0.028887(17) 0.156222(5) 0.01142(5) Uani 1 1 d .
N1 N 0.09199(17) -0.2234(2) 0.13477(6) 0.0161(3) Uani 1 1 d D
H01A H 0.0183(18) -0.213(2) 0.1467(6) 0.006(5) Uiso 1 1 d D
H01B H 0.128(2) -0.303(3) 0.1476(8) 0.024(7) Uiso 1 1 d D
P1 P 0.34351(5) 0.17678(6) 0.181559(16) 0.01348(10) Uani 1 1 d .
Br1 Br 0.412059(19) -0.22017(2) 0.154921(7) 0.01962(6) Uani 1 1 d .
C1 C 0.12420(18) 0.1794(2) 0.07940(6) 0.0125(4) Uani 1 1 d .
C2 C 0.12317(18) 0.0342(2) 0.05598(6) 0.0131(4) Uani 1 1 d .
C3 C 0.21201(19) 0.0160(2) 0.02247(6) 0.0145(4) Uani 1 1 d .
H3 H 0.2107 -0.0824 0.0062 0.017 Uiso 1 1 calc R
C4 C 0.30075(18) 0.1370(2) 0.01262(6) 0.0136(4) Uani 1 1 d .
C5 C 0.30385(18) 0.2826(2) 0.03713(6) 0.0138(4) Uani 1 1 d .
C6 C 0.21345(18) 0.3041(2) 0.06880(6) 0.0137(4) Uani 1 1 d .
H6 H 0.2113 0.4052 0.0838 0.016 Uiso 1 1 calc R
C7 C 0.03445(18) 0.2041(2) 0.11623(6) 0.0124(4) Uani 1 1 d .
C8 C 0.05627(17) 0.1152(2) 0.15223(6) 0.0121(3) Uani 1 1 d .
C9 C 0.0814(2) -0.2516(2) 0.08764(7) 0.0173(4) Uani 1 1 d .
H9A H 0.0235 -0.3470 0.0818 0.021 Uiso 1 1 calc R
H9B H 0.1700 -0.2778 0.0771 0.021 Uiso 1 1 calc R
C10 C 0.02591(18) -0.1035(2) 0.06309(6) 0.0151(4) Uani 1 1 d .
H10A H -0.0093 -0.1410 0.0347 0.018 Uiso 1 1 calc R
H10B H -0.0491 -0.0593 0.0790 0.018 Uiso 1 1 calc R
C11 C -0.07150(18) 0.3288(2) 0.11068(6) 0.0128(4) Uani 1 1 d .
C12 C -0.13307(19) 0.3586(2) 0.07025(7) 0.0175(4) Uani 1 1 d .
H12 H -0.1084 0.2958 0.0461 0.021 Uiso 1 1 calc R
C13 C -0.2293(2) 0.4783(3) 0.06505(7) 0.0240(5) Uani 1 1 d .
H13 H -0.2716 0.4950 0.0377 0.029 Uiso 1 1 calc R
C14 C -0.2641(2) 0.5741(3) 0.09987(7) 0.0225(4) Uani 1 1 d .
H14 H -0.3293 0.6568 0.0962 0.027 Uiso 1 1 calc R
C15 C -0.2037(2) 0.5486(2) 0.13954(7) 0.0190(4) Uani 1 1 d .
H15 H -0.2273 0.6140 0.1633 0.023 Uiso 1 1 calc R
C16 C -0.10810(19) 0.4273(2) 0.14513(6) 0.0155(4) Uani 1 1 d .
H16 H -0.0671 0.4111 0.1727 0.019 Uiso 1 1 calc R
C21 C -0.04048(18) 0.0838(2) 0.18584(6) 0.0130(4) Uani 1 1 d .
C22 C -0.16267(19) 0.0139(2) 0.17348(6) 0.0157(4) Uani 1 1 d .
H22 H -0.1858 0.0032 0.1438 0.019 Uiso 1 1 calc R
C23 C -0.25020(19) -0.0397(2) 0.20365(7) 0.0185(4) Uani 1 1 d .
H23 H -0.3313 -0.0890 0.1945 0.022 Uiso 1 1 calc R
C24 C -0.2197(2) -0.0214(3) 0.24721(7) 0.0186(4) Uani 1 1 d .
H24 H -0.2790 -0.0593 0.2680 0.022 Uiso 1 1 calc R
C25 C -0.1013(2) 0.0529(2) 0.26014(6) 0.0175(4) Uani 1 1 d .
H25 H -0.0816 0.0703 0.2899 0.021 Uiso 1 1 calc R
C26 C -0.01162(18) 0.1019(2) 0.22989(6) 0.0147(4) Uani 1 1 d .
H26 H 0.0704 0.1484 0.2393 0.018 Uiso 1 1 calc R
C27 C 0.3816(2) -0.0071(3) -0.04790(7) 0.0212(4) Uani 1 1 d .
H27A H 0.4010 -0.1066 -0.0313 0.032 Uiso 1 1 calc R
H27B H 0.4467 0.0054 -0.0702 0.032 Uiso 1 1 calc R
H27C H 0.2929 -0.0150 -0.0613 0.032 Uiso 1 1 calc R
O1 O 0.38799(14) 0.13144(17) -0.01989(4) 0.0181(3) Uani 1 1 d .
C28 C 0.3990(2) 0.5465(3) 0.04802(7) 0.0221(4) Uani 1 1 d .
H28A H 0.3155 0.6029 0.0414 0.033 Uiso 1 1 calc R
H28B H 0.4725 0.6131 0.0382 0.033 Uiso 1 1 calc R
H28C H 0.4091 0.5293 0.0791 0.033 Uiso 1 1 calc R
O2 O 0.39912(13) 0.39207(17) 0.02657(4) 0.0167(3) Uani 1 1 d .
C31 C 0.2678(2) 0.3752(2) 0.18893(7) 0.0194(4) Uani 1 1 d .
H31A H 0.3355 0.4542 0.1984 0.029 Uiso 1 1 calc R
H31B H 0.2006 0.3670 0.2107 0.029 Uiso 1 1 calc R
H31C H 0.2263 0.4117 0.1617 0.029 Uiso 1 1 calc R
C32 C 0.4176(2) 0.1362(3) 0.23471(7) 0.0203(4) Uani 1 1 d .
H32A H 0.4838 0.2202 0.2418 0.030 Uiso 1 1 calc R
H32B H 0.4600 0.0285 0.2348 0.030 Uiso 1 1 calc R
H32C H 0.3489 0.1380 0.2561 0.030 Uiso 1 1 calc R
C33 C 0.4837(2) 0.2207(3) 0.14867(7) 0.0199(4) Uani 1 1 d .
H33A H 0.4521 0.2560 0.1200 0.030 Uiso 1 1 calc R
H33B H 0.5377 0.1220 0.1461 0.030 Uiso 1 1 calc R
H33C H 0.5371 0.3078 0.1622 0.030 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
C8 Pd1 N1 87.01(7)
C8 Pd1 P1 91.94(5)
N1 Pd1 P1 177.44(5)
C8 Pd1 Br1 174.97(5)
N1 Pd1 Br1 89.37(5)
P1 Pd1 Br1 91.807(15)
C9 N1 Pd1 116.62(12)
C31 P1 C33 103.72(10)
C31 P1 C32 102.17(10)
C33 P1 C32 104.00(10)
C31 P1 Pd1 118.46(7)
C33 P1 Pd1 113.57(7)
C32 P1 Pd1 113.25(7)
C2 C1 C6 119.17(17)
C2 C1 C7 121.36(17)
C6 C1 C7 119.46(17)
C1 C2 C3 118.93(17)
C1 C2 C10 123.31(17)
C3 C2 C10 117.68(17)
C4 C3 C2 121.83(17)
O1 C4 C3 125.76(17)
O1 C4 C5 115.10(17)
C3 C4 C5 119.13(17)
O2 C5 C6 125.52(17)
O2 C5 C4 115.14(16)
C6 C5 C4 119.33(17)
C5 C6 C1 121.47(18)
C8 C7 C11 124.33(17)
C8 C7 C1 118.40(16)
C11 C7 C1 117.26(16)
C7 C8 C21 125.98(17)
C7 C8 Pd1 118.48(13)
C21 C8 Pd1 114.17(13)
N1 C9 C10 112.51(16)
C2 C10 C9 115.57(16)
C16 C11 C12 117.64(17)
C16 C11 C7 121.00(17)
C12 C11 C7 121.26(17)
C13 C12 C11 120.97(19)
C12 C13 C14 120.2(2)
C15 C14 C13 119.78(19)
C14 C15 C16 120.39(19)
C15 C16 C11 121.04(19)
C26 C21 C22 117.59(17)
C26 C21 C8 123.55(17)
C22 C21 C8 118.43(17)
C23 C22 C21 121.48(18)
C22 C23 C24 120.13(18)
C23 C24 C25 119.31(18)
C26 C25 C24 120.51(19)
C25 C26 C21 120.90(18)
C4 O1 C27 117.44(16)
C5 O2 C28 117.08(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Pd1 C8 2.0091(18)
Pd1 N1 2.1252(17)
Pd1 P1 2.2424(5)
Pd1 Br1 2.5237(3)
N1 C9 1.485(3)
P1 C31 1.814(2)
P1 C33 1.816(2)
P1 C32 1.823(2)
C1 C2 1.394(3)
C1 C6 1.410(3)
C1 C7 1.502(3)
C2 C3 1.409(3)
C2 C10 1.518(3)
C3 C4 1.379(3)
C4 O1 1.367(2)
C4 C5 1.415(3)
C5 O2 1.365(2)
C5 C6 1.380(3)
C7 C8 1.348(3)
C7 C11 1.486(3)
C8 C21 1.481(3)
C9 C10 1.528(3)
C11 C16 1.401(3)
C11 C12 1.406(3)
C12 C13 1.388(3)
C13 C14 1.392(3)
C14 C15 1.374(3)
C15 C16 1.393(3)
C21 C26 1.399(3)
C21 C22 1.405(3)
C22 C23 1.385(3)
C23 C24 1.388(3)
C24 C25 1.392(3)
C25 C26 1.390(3)
C27 O1 1.429(2)
C28 O2 1.429(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
C13 H13 O2 0.95 2.52 3.445(3) 165.4 3_565
C28 H28B O1 0.98 2.60 3.535(2) 160.2 3_665
