#------------------------------------------------------------------------------
#$Date: 2016-03-21 11:07:37 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178681 $
#$URL: svn://www.crystallography.net/cod/cif/4/07/92/4079232.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_4079232
loop_
_publ_author_name
'García-López, José-Antonio'
'Oliva-Madrid, María-José'
'Saura-Llamas, Isabel'
'Bautista, Delia'
'Vicente, José'
_publ_section_title
;
 Reactivity toward CO of Eight-Membered Palladacycles Derived from the
 Insertion of Alkenes into the Pd--C Bond of Cyclopalladated Primary
 Arylalkylamines of Pharmaceutical Interest. Synthesis of
 Tetrahydrobenzazocinones, Ortho-Functionalized Phenethylamines, Ureas,
 and an Isocyanate
;
_journal_issue                   17
_journal_name_full               Organometallics
_journal_page_first              6351
_journal_paper_doi               10.1021/om300593x
_journal_volume                  31
_journal_year                    2012
_chemical_formula_sum            'C20 H27 Br N2 O3 Pd'
_chemical_formula_weight         529.75
_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                 138.854(17)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.1033(15)
_cell_length_b                   7.55022(17)
_cell_length_c                   24.464(2)
_cell_measurement_reflns_used    3756
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.3510
_cell_measurement_theta_min      2.3848
_cell_volume                     2078.6(8)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.18t (release 05-06-2012 CrysAlis171 .NET)
(compiled Jun  5 2012,17:40:27)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.18t (release 05-06-2012 CrysAlis171 .NET)
(compiled Jun  5 2012,17:40:27)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.18t (release 05-06-2012 CrysAlis171 .NET)
(compiled Jun  5 2012,17:40:27)
;
_computing_molecular_graphics    ShelxTL
_computing_publication_material  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 10.4948
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.839
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_sigmaI/netI    0.0610
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            9084
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         29.42
_diffrn_reflns_theta_min         2.39
_exptl_absorpt_coefficient_mu    2.841
_exptl_absorpt_correction_T_max  0.935
_exptl_absorpt_correction_T_min  0.784
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.18t (release 05-06-2012 CrysAlis171 .NET)
(compiled Jun  5 2012,17:40:27)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_density_diffrn    1.693
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.780
_refine_diff_density_min         -0.798
_refine_diff_density_rms         0.128
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment
'NH2 free with SADI, rigid methyls, others riding'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         4833
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0571
_refine_ls_R_factor_gt           0.0399
_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)+(0.0251P)²+1.1627P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0724
_refine_ls_wR_factor_ref         0.0797
_reflns_number_gt                3871
_reflns_number_total             4833
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om300593x_si_002.cif
_cod_data_source_block           joe951a
_cod_original_cell_volume        2078.6(7)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4079232
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
Pd1 Pd 0.72642(2) 0.59919(4) 0.698479(16) 0.01291(8) Uani 1 1 d .
N1 N 0.5625(3) 0.4822(4) 0.62127(19) 0.0149(6) Uani 1 1 d D
H01A H 0.508(3) 0.557(4) 0.5791(19) 0.014(10) Uiso 1 1 d D
H01B H 0.568(3) 0.392(4) 0.602(2) 0.010(9) Uiso 1 1 d D
N2 N 0.8896(2) 0.7093(4) 0.77250(18) 0.0138(6) Uani 1 1 d .
Br1 Br 0.82087(3) 0.30060(5) 0.75982(2) 0.02265(11) Uani 1 1 d .
C1 C 0.6452(3) 0.8460(5) 0.6471(2) 0.0135(7) Uani 1 1 d .
H1 H 0.7076 0.9399 0.6771 0.016 Uiso 1 1 calc R
C2 C 0.5617(3) 0.8884(5) 0.6507(2) 0.0151(7) Uani 1 1 d .
H2A H 0.5415 1.0160 0.6393 0.018 Uiso 1 1 calc R
H2B H 0.4872 0.8203 0.6071 0.018 Uiso 1 1 calc R
C3 C 0.6176(3) 0.8436(5) 0.7349(2) 0.0156(8) Uani 1 1 d .
C4 C 0.5920(3) 0.6893(5) 0.7498(2) 0.0168(8) Uani 1 1 d .
C5 C 0.6561(3) 0.6515(5) 0.8317(2) 0.0198(8) Uani 1 1 d .
H5 H 0.6395 0.5454 0.8424 0.024 Uiso 1 1 calc R
C6 C 0.7426(3) 0.7651(5) 0.8968(2) 0.0191(8) Uani 1 1 d .
C7 C 0.7665(3) 0.9217(5) 0.8811(2) 0.0188(8) Uani 1 1 d .
C8 C 0.7041(3) 0.9601(5) 0.8008(2) 0.0147(8) Uani 1 1 d .
H8 H 0.7201 1.0672 0.7902 0.018 Uiso 1 1 calc R
C9 C 0.8118(4) 0.5677(6) 1.0023(3) 0.0373(12) Uani 1 1 d .
H9A H 0.7327 0.5346 0.9739 0.056 Uiso 1 1 calc R
H9B H 0.8684 0.5650 1.0625 0.056 Uiso 1 1 calc R
H9C H 0.8372 0.4839 0.9874 0.056 Uiso 1 1 calc R
O1 O 0.8077(3) 0.7399(4) 0.97799(16) 0.0295(7) Uani 1 1 d .
C10 C 0.8865(4) 1.1829(5) 0.9367(2) 0.0267(9) Uani 1 1 d .
H10A H 0.9166 1.1464 0.9167 0.040 Uiso 1 1 calc R
H10B H 0.9491 1.2457 0.9896 0.040 Uiso 1 1 calc R
H10C H 0.8180 1.2614 0.8957 0.040 Uiso 1 1 calc R
O2 O 0.8510(2) 1.0296(4) 0.94836(15) 0.0229(6) Uani 1 1 d .
C11 C 0.4956(3) 0.5603(5) 0.6819(2) 0.0176(8) Uani 1 1 d .
H11A H 0.4295 0.6292 0.6310 0.021 Uiso 1 1 calc R
H11B H 0.4645 0.5020 0.6988 0.021 Uiso 1 1 calc R
C12 C 0.5308(3) 0.4156(5) 0.6597(2) 0.0167(8) Uani 1 1 d .
H12A H 0.5995 0.3496 0.7109 0.020 Uiso 1 1 calc R
H12B H 0.4640 0.3312 0.6209 0.020 Uiso 1 1 calc R
C13 C 0.5914(3) 0.8168(5) 0.5647(2) 0.0149(8) Uani 1 1 d .
O3 O 0.4895(2) 0.7597(3) 0.50482(15) 0.0175(6) Uani 1 1 d .
C14 C 0.6669(3) 0.8626(5) 0.5558(2) 0.0196(8) Uani 1 1 d .
H14A H 0.6403 0.7941 0.5100 0.029 Uiso 1 1 calc R
H14B H 0.7501 0.8343 0.6075 0.029 Uiso 1 1 calc R
H14C H 0.6595 0.9894 0.5439 0.029 Uiso 1 1 calc R
C15 C 0.9618(3) 0.6434(5) 0.7718(2) 0.0174(8) Uani 1 1 d .
H15 H 0.9331 0.5504 0.7341 0.021 Uiso 1 1 calc R
C16 C 1.0759(3) 0.7048(5) 0.8236(2) 0.0180(8) Uani 1 1 d .
H16 H 1.1236 0.6559 0.8204 0.022 Uiso 1 1 calc R
C17 C 1.1206(3) 0.8384(5) 0.8802(2) 0.0180(8) Uani 1 1 d .
C18 C 1.0455(3) 0.9084(5) 0.8798(2) 0.0191(8) Uani 1 1 d .
H18 H 1.0716 1.0026 0.9163 0.023 Uiso 1 1 calc R
C19 C 0.9322(3) 0.8403(5) 0.8259(2) 0.0177(8) Uani 1 1 d .
H19 H 0.8821 0.8892 0.8269 0.021 Uiso 1 1 calc R
C20 C 1.2441(3) 0.9058(5) 0.9377(2) 0.0238(9) Uani 1 1 d .
H20A H 1.2523 0.9563 0.9053 0.036 Uiso 1 1 calc R
H20B H 1.3006 0.8081 0.9718 0.036 Uiso 1 1 calc R
H20C H 1.2606 0.9975 0.9737 0.036 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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-15 0 -2 0.0148 -15.0000 -0.0000 -2.0000 -1.0129 0.0322 -0.0055
15 0 2 0.0148 15.0000 0.0000 2.0000 1.0129 -0.0322 0.0055
17 4 -31 0.0475 17.0000 4.0000 -31.0000 -0.0047 -0.0307 -0.9749
-17 -4 31 0.0475 -17.0000 -4.0000 31.0000 0.0047 0.0307 0.9749
18 0 -34 0.0183 18.0000 -0.0000 -34.0000 -0.0583 -0.4062 -0.8970
-18 0 34 0.0037 -18.0000 0.0000 34.0000 0.0583 0.4062 0.8970
7 -10 -15 0.0984 7.0000 -10.0000 -15.0000 -0.1137 -1.0303 -0.0046
1 11 1 0.0831 1.0000 11.0000 1.0000 0.1296 0.9464 -0.4054
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N2 Pd1 N1 177.65(12)
N2 Pd1 C1 90.90(13)
N1 Pd1 C1 90.11(13)
N2 Pd1 Br1 90.05(9)
N1 Pd1 Br1 88.96(9)
C1 Pd1 Br1 178.92(10)
C12 N1 Pd1 117.4(2)
C19 N2 C15 117.2(3)
C19 N2 Pd1 123.0(2)
C15 N2 Pd1 119.7(2)
C13 C1 C2 117.6(3)
C13 C1 Pd1 98.0(2)
C2 C1 Pd1 112.2(2)
C3 C2 C1 111.8(3)
C4 C3 C8 119.6(3)
C4 C3 C2 122.9(3)
C8 C3 C2 117.4(3)
C3 C4 C5 118.8(3)
C3 C4 C11 123.3(3)
C5 C4 C11 117.9(3)
C6 C5 C4 121.6(4)
O1 C6 C5 125.3(4)
O1 C6 C7 115.3(3)
C5 C6 C7 119.3(3)
O2 C7 C8 124.5(3)
O2 C7 C6 115.9(3)
C8 C7 C6 119.6(3)
C7 C8 C3 121.1(3)
C6 O1 C9 117.8(3)
C7 O2 C10 117.6(3)
C4 C11 C12 116.9(3)
N1 C12 C11 114.3(3)
O3 C13 C1 123.0(3)
O3 C13 C14 120.6(3)
C1 C13 C14 116.4(3)
N2 C15 C16 122.8(3)
C15 C16 C17 119.7(3)
C18 C17 C16 117.4(3)
C18 C17 C20 121.6(3)
C16 C17 C20 121.0(3)
C19 C18 C17 119.5(4)
N2 C19 C18 123.3(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Pd1 N2 2.037(3)
Pd1 N1 2.058(3)
Pd1 C1 2.086(3)
Pd1 Br1 2.5085(5)
N1 C12 1.482(4)
N2 C19 1.335(5)
N2 C15 1.343(4)
C1 C13 1.471(5)
C1 C2 1.531(5)
C2 C3 1.518(5)
C3 C4 1.387(5)
C3 C8 1.403(5)
C4 C5 1.409(5)
C4 C11 1.517(5)
C5 C6 1.383(5)
C6 O1 1.375(4)
C6 C7 1.395(5)
C7 O2 1.370(4)
C7 C8 1.388(5)
C9 O1 1.409(5)
C10 O2 1.432(5)
C11 C12 1.531(5)
C13 O3 1.235(4)
C13 C14 1.503(5)
C15 C16 1.381(5)
C16 C17 1.387(5)
C17 C18 1.382(5)
C17 C20 1.492(5)
C18 C19 1.382(5)
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 H01A O3 0.90(3) 2.21(3) 2.951(4) 140(3) .
N1 H01B O3 0.88(3) 2.28(3) 3.084(4) 152(3) 3_666
