#------------------------------------------------------------------------------
#$Date: 2016-03-21 11:07:37 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178681 $
#$URL: svn://www.crystallography.net/cod/cif/4/07/92/4079236.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_4079236
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            'C14 H22 Cl N O'
_chemical_formula_weight         255.78
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   8.3839(3)
_cell_length_b                   9.2671(4)
_cell_length_c                   37.1174(15)
_cell_measurement_reflns_used    9202
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.93
_cell_measurement_theta_min      2.19
_cell_volume                     2883.8(2)
_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      293(2)
_diffrn_detector_area_resol_mean 8.26
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.956
_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  0.0475
_diffrn_reflns_av_sigmaI/netI    0.0280
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       48
_diffrn_reflns_limit_l_min       -49
_diffrn_reflns_number            30938
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         28.21
_diffrn_reflns_theta_min         2.19
_exptl_absorpt_coefficient_mu    0.251
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.178
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.438
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_hydrogen_treatment
'NH3 free with SADI, rigid methyl, others riding'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         3405
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.121
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0461
_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)+(0.0557P)²+0.9621P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1072
_refine_ls_wR_factor_ref         0.1117
_reflns_number_gt                3047
_reflns_number_total             3405
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om300593x_si_002.cif
_cod_data_source_block           jae923m
_cod_original_sg_symbol_H-M      'P bca'
_cod_database_code               4079236
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, 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
N1 N 0.08231(15) -0.02834(15) 0.28200(3) 0.0168(3) Uani 1 1 d D
H01A H 0.084(2) -0.1277(16) 0.2807(5) 0.031(6) Uiso 1 1 d D
H01B H 0.1822(19) 0.006(2) 0.2838(5) 0.025(5) Uiso 1 1 d D
H01C H 0.037(2) 0.008(2) 0.2618(4) 0.029(5) Uiso 1 1 d D
O1 O 0.35817(15) -0.05967(12) 0.46185(3) 0.0255(3) Uani 1 1 d .
C1 C -0.00053(17) -0.02138(15) 0.38361(4) 0.0147(3) Uani 1 1 d .
C2 C -0.13744(18) -0.09540(16) 0.39472(4) 0.0187(3) Uani 1 1 d .
H2 H -0.1811 -0.1651 0.3797 0.022 Uiso 1 1 calc R
C3 C -0.20970(19) -0.06757(17) 0.42759(4) 0.0220(3) Uani 1 1 d .
H3 H -0.3018 -0.1168 0.4342 0.026 Uiso 1 1 calc R
C4 C -0.1438(2) 0.03400(17) 0.45056(4) 0.0232(3) Uani 1 1 d .
H4 H -0.1912 0.0533 0.4727 0.028 Uiso 1 1 calc R
C5 C -0.00684(19) 0.10663(16) 0.44026(4) 0.0201(3) Uani 1 1 d .
H5 H 0.0375 0.1741 0.4559 0.024 Uiso 1 1 calc R
C6 C 0.06687(17) 0.08137(15) 0.40698(4) 0.0156(3) Uani 1 1 d .
C7 C 0.21835(18) 0.16284(16) 0.39815(4) 0.0178(3) Uani 1 1 d .
H7A H 0.2165 0.2548 0.4106 0.021 Uiso 1 1 calc R
H7B H 0.2204 0.1826 0.3725 0.021 Uiso 1 1 calc R
C8 C 0.37268(18) 0.08181(16) 0.40852(4) 0.0182(3) Uani 1 1 d .
H8A H 0.3755 -0.0107 0.3963 0.022 Uiso 1 1 calc R
H8B H 0.4646 0.1373 0.4007 0.022 Uiso 1 1 calc R
C9 C 0.38114(17) 0.05828(16) 0.44886(4) 0.0181(3) Uani 1 1 d .
C10 C 0.4164(2) 0.18701(17) 0.47198(5) 0.0264(4) Uani 1 1 d .
H10A H 0.3702 0.1733 0.4954 0.040 Uiso 1 1 calc R
H10B H 0.3718 0.2718 0.4611 0.040 Uiso 1 1 calc R
H10C H 0.5297 0.1984 0.4743 0.040 Uiso 1 1 calc R
C11 C 0.07066(16) -0.05616(16) 0.34712(4) 0.0149(3) Uani 1 1 d .
H11A H 0.0656 -0.1597 0.3435 0.018 Uiso 1 1 calc R
H11B H 0.1824 -0.0289 0.3473 0.018 Uiso 1 1 calc R
C12 C -0.01110(17) 0.01885(17) 0.31480(4) 0.0170(3) Uani 1 1 d .
C13 C -0.0024(2) 0.18281(17) 0.31648(4) 0.0231(4) Uani 1 1 d .
H13A H 0.1072 0.2126 0.3168 0.035 Uiso 1 1 calc R
H13B H -0.0545 0.2161 0.3380 0.035 Uiso 1 1 calc R
H13C H -0.0545 0.2231 0.2958 0.035 Uiso 1 1 calc R
C14 C -0.18163(18) -0.0330(2) 0.30912(4) 0.0270(4) Uani 1 1 d .
H14A H -0.2242 0.0100 0.2876 0.041 Uiso 1 1 calc R
H14B H -0.2458 -0.0055 0.3294 0.041 Uiso 1 1 calc R
H14C H -0.1824 -0.1361 0.3067 0.041 Uiso 1 1 calc R
Cl1 Cl 0.42101(4) 0.12219(4) 0.285910(10) 0.01996(13) Uani 1 1 d .
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'
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
C2 C1 C6 118.67(14)
C2 C1 C11 118.84(13)
C6 C1 C11 122.48(13)
C3 C2 C1 121.78(15)
C4 C3 C2 119.60(15)
C3 C4 C5 119.41(15)
C4 C5 C6 121.86(15)
C5 C6 C1 118.66(14)
C5 C6 C7 118.53(13)
C1 C6 C7 122.79(13)
C6 C7 C8 113.99(12)
C9 C8 C7 110.81(12)
O1 C9 C10 121.49(15)
O1 C9 C8 121.09(14)
C10 C9 C8 117.42(13)
C1 C11 C12 115.04(12)
N1 C12 C13 107.27(12)
N1 C12 C14 106.46(12)
C13 C12 C14 111.43(13)
N1 C12 C11 105.36(11)
C13 C12 C11 113.30(13)
C14 C12 C11 112.45(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C12 1.5122(19)
O1 C9 1.2100(19)
C1 C2 1.399(2)
C1 C6 1.406(2)
C1 C11 1.515(2)
C2 C3 1.386(2)
C3 C4 1.385(2)
C4 C5 1.385(2)
C5 C6 1.401(2)
C6 C7 1.513(2)
C7 C8 1.545(2)
C8 C9 1.515(2)
C9 C10 1.499(2)
C11 C12 1.547(2)
C12 C13 1.523(2)
C12 C14 1.523(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
N1 H01B Cl1 0.899(15) 2.274(15) 3.1672(13) 172.3(18) .
N1 H01A Cl1 0.922(15) 2.326(15) 3.2419(15) 172.1(17) 7_655
N1 H01C Cl1 0.906(14) 2.280(15) 3.1826(13) 174.1(17) 6_556
C10 H10B O1 0.96 2.48 3.309(2) 144.4 7_665
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C6 C1 C2 C3 1.5(2)
C11 C1 C2 C3 -179.22(13)
C1 C2 C3 C4 -1.3(2)
C2 C3 C4 C5 0.2(2)
C3 C4 C5 C6 0.6(2)
C4 C5 C6 C1 -0.3(2)
C4 C5 C6 C7 -178.63(14)
C2 C1 C6 C5 -0.7(2)
C11 C1 C6 C5 -179.93(13)
C2 C1 C6 C7 177.50(13)
C11 C1 C6 C7 -1.7(2)
C5 C6 C7 C8 92.64(17)
C1 C6 C7 C8 -85.58(17)
C6 C7 C8 C9 -62.76(16)
C7 C8 C9 O1 106.07(16)
C7 C8 C9 C10 -72.98(17)
C2 C1 C11 C12 81.39(17)
C6 C1 C11 C12 -99.40(16)
C1 C11 C12 N1 178.43(12)
C1 C11 C12 C13 61.46(17)
C1 C11 C12 C14 -66.01(17)
