#------------------------------------------------------------------------------
#$Date: 2016-03-25 11:14:35 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179781 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/77/7007779.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_7007779
loop_
_publ_author_name
'Cardile, Steven A.'
'Jennings, Michael C.'
'Jones, Nathan D.'
_publ_section_title
;
 Pyridinyloxazolidines: versatile scaffolds for chiral catalyst
 construction.
;
_journal_issue                   39
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              4672
_journal_page_last               4678
_journal_paper_doi               10.1039/b610079a
_journal_year                    2006
_chemical_formula_sum            'C17 H19 Cl5 N2 O Pd'
_chemical_formula_weight         550.99
_chemical_name_systematic
;
?
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.9866(2)
_cell_length_b                   14.0192(4)
_cell_length_c                   17.0694(4)
_cell_measurement_reflns_used    2809
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.70
_cell_volume                     2150.49(9)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1997-2001)'
_computing_data_reduction        DENZO-SMN
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 2001)'
_computing_publication_material  SHELXTL/PC
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Nonius Kappa-CCD'
_diffrn_measurement_method       'φ scans, and ω scans with κ offsets'
_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  0.0610
_diffrn_reflns_av_sigmaI/netI    0.0345
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            22310
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.56
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.493
_exptl_absorpt_correction_T_max  0.9291
_exptl_absorpt_correction_T_min  0.4613
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO-SMN (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.702
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.61
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.05(4)
_refine_ls_extinction_coef       0.0029(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3792
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.113
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0383
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0505P)²+0.4599P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0902
_refine_ls_wR_factor_ref         0.0951
_reflns_number_gt                3192
_reflns_number_total             3792
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b610079a.txt
_cod_data_source_block           11ox
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7007779
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -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
Pd Pd 0.90860(4) 1.33557(3) 0.42902(2) 0.05077(15) Uani 1 1 d . . .
Cl1 Cl 0.76166(19) 1.36706(13) 0.53435(9) 0.0814(5) Uani 1 1 d . . .
Cl2 Cl 0.99514(16) 1.48929(10) 0.43423(10) 0.0732(4) Uani 1 1 d . . .
O O 0.8499(4) 1.0762(3) 0.3231(3) 0.0732(12) Uani 1 1 d . . .
N1 N 0.8315(4) 1.1963(3) 0.4190(3) 0.0517(10) Uani 1 1 d . . .
N2 N 1.0319(5) 1.3001(3) 0.3348(3) 0.0553(11) Uani 1 1 d . . .
C2 C 0.9316(6) 1.1447(4) 0.3645(3) 0.0581(14) Uani 1 1 d . . .
H2 H 1.0049 1.1105 0.3964 0.070 Uiso 1 1 calc R . .
C4 C 0.6812(6) 1.1858(4) 0.3795(3) 0.0538(14) Uani 1 1 d . . .
H4 H 0.6035 1.1832 0.4198 0.065 Uiso 1 1 calc R . .
C5 C 0.6929(6) 1.0872(4) 0.3392(4) 0.0591(15) Uani 1 1 d . . .
H5 H 0.6649 1.0386 0.3778 0.071 Uiso 1 1 calc R . .
C6 C 0.8320(8) 1.1439(5) 0.4955(3) 0.0769(18) Uani 1 1 d . . .
H6A H 0.7956 1.0802 0.4877 0.115 Uiso 1 1 calc R . .
H6B H 0.7691 1.1766 0.5322 0.115 Uiso 1 1 calc R . .
H6C H 0.9317 1.1414 0.5157 0.115 Uiso 1 1 calc R . .
C7 C 0.6465(7) 1.2660(4) 0.3230(4) 0.0656(16) Uani 1 1 d . . .
H7A H 0.6406 1.3252 0.3512 0.098 Uiso 1 1 calc R . .
H7B H 0.5531 1.2537 0.2977 0.098 Uiso 1 1 calc R . .
H7C H 0.7238 1.2701 0.2843 0.098 Uiso 1 1 calc R . .
C8 C 0.6038(7) 1.0699(4) 0.2671(3) 0.0585(13) Uani 1 1 d . . .
C9 C 0.4580(7) 1.0413(5) 0.2737(4) 0.080(2) Uani 1 1 d . . .
H9 H 0.4141 1.0348 0.3228 0.096 Uiso 1 1 calc R . .
C10 C 0.3774(9) 1.0221(5) 0.2060(6) 0.102(3) Uani 1 1 d . . .
H10 H 0.2793 1.0018 0.2102 0.122 Uiso 1 1 calc R . .
C11 C 0.4396(12) 1.0326(6) 0.1333(5) 0.101(3) Uani 1 1 d . . .
H11 H 0.3853 1.0181 0.0885 0.121 Uiso 1 1 calc R . .
C12 C 0.5784(11) 1.0639(5) 0.1279(4) 0.093(2) Uani 1 1 d . . .
H12 H 0.6193 1.0734 0.0785 0.112 Uiso 1 1 calc R . .
C13 C 0.6636(8) 1.0825(4) 0.1924(4) 0.0779(18) Uani 1 1 d . . .
H13 H 0.7611 1.1036 0.1865 0.093 Uiso 1 1 calc R . .
C14 C 1.0161(6) 1.2096(4) 0.3104(3) 0.0571(14) Uani 1 1 d . . .
C15 C 1.0819(8) 1.1767(5) 0.2421(4) 0.0807(18) Uani 1 1 d . . .
H15 H 1.0658 1.1146 0.2250 0.097 Uiso 1 1 calc R . .
C16 C 1.1700(9) 1.2365(6) 0.2009(5) 0.101(3) Uani 1 1 d . . .
H16 H 1.2170 1.2154 0.1555 0.122 Uiso 1 1 calc R . .
C17 C 1.1898(8) 1.3295(6) 0.2265(4) 0.093(2) Uani 1 1 d . . .
H17 H 1.2504 1.3711 0.1986 0.112 Uiso 1 1 calc R . .
C18 C 1.1200(6) 1.3594(4) 0.2929(4) 0.0703(16) Uani 1 1 d . . .
H18 H 1.1332 1.4220 0.3097 0.084 Uiso 1 1 calc R . .
C1A C 1.2312(8) 1.1349(5) -0.0638(4) 0.103(2) Uani 1 1 d D . .
H1A H 1.2060 1.0832 -0.0275 0.123 Uiso 1 1 calc R . .
Cl3A Cl 1.3046(5) 1.2297(3) -0.01189(17) 0.1797(14) Uani 1 1 d D . .
Cl3B Cl 1.3634(3) 1.0936(2) -0.1328(2) 0.1476(11) Uani 1 1 d D . .
Cl3C Cl 1.0716(3) 1.17055(19) -0.11425(13) 0.1202(7) Uani 1 1 d 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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Pd N1 83.45(17) . . ?
N2 Pd Cl1 176.49(14) . . ?
N1 Pd Cl1 93.10(12) . . ?
N2 Pd Cl2 94.37(13) . . ?
N1 Pd Cl2 177.47(13) . . ?
Cl1 Pd Cl2 89.07(6) . . ?
C2 O C5 110.1(4) . . ?
C2 N1 C6 107.9(4) . . ?
C2 N1 C4 102.4(4) . . ?
C6 N1 C4 110.0(4) . . ?
C2 N1 Pd 107.9(3) . . ?
C6 N1 Pd 112.8(3) . . ?
C4 N1 Pd 115.1(3) . . ?
C14 N2 C18 118.5(5) . . ?
C14 N2 Pd 115.0(4) . . ?
C18 N2 Pd 126.3(4) . . ?
O C2 N1 109.5(4) . . ?
O C2 C14 111.7(5) . . ?
N1 C2 C14 113.4(4) . . ?
O C2 H2 107.3 . . ?
N1 C2 H2 107.3 . . ?
C14 C2 H2 107.3 . . ?
C7 C4 N1 113.2(4) . . ?
C7 C4 C5 113.2(4) . . ?
N1 C4 C5 102.9(4) . . ?
C7 C4 H4 109.1 . . ?
N1 C4 H4 109.1 . . ?
C5 C4 H4 109.1 . . ?
O C5 C8 110.5(5) . . ?
O C5 C4 104.2(4) . . ?
C8 C5 C4 118.4(5) . . ?
O C5 H5 107.7 . . ?
C8 C5 H5 107.7 . . ?
C4 C5 H5 107.7 . . ?
N1 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C13 118.7(6) . . ?
C9 C8 C5 119.4(6) . . ?
C13 C8 C5 121.9(5) . . ?
C8 C9 C10 119.0(7) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 H9 120.5 . . ?
C11 C10 C9 121.4(8) . . ?
C11 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C12 C11 C10 118.8(8) . . ?
C12 C11 H11 120.6 . . ?
C10 C11 H11 120.6 . . ?
C11 C12 C13 122.4(9) . . ?
C11 C12 H12 118.8 . . ?
C13 C12 H12 118.8 . . ?
C12 C13 C8 119.7(7) . . ?
C12 C13 H13 120.2 . . ?
C8 C13 H13 120.2 . . ?
N2 C14 C15 122.0(5) . . ?
N2 C14 C2 115.8(5) . . ?
C15 C14 C2 122.1(5) . . ?
C16 C15 C14 118.8(6) . . ?
C16 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
C15 C16 C17 119.6(6) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
C18 C17 C16 119.6(7) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
N2 C18 C17 121.4(6) . . ?
N2 C18 H18 119.3 . . ?
C17 C18 H18 119.3 . . ?
Cl3A C1A Cl3C 110.3(4) . . ?
Cl3A C1A Cl3B 109.7(4) . . ?
Cl3C C1A Cl3B 108.4(4) . . ?
Cl3A C1A H1A 109.5 . . ?
Cl3C C1A H1A 109.5 . . ?
Cl3B C1A H1A 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Pd N2 2.015(4) . ?
Pd N1 2.079(4) . ?
Pd Cl1 2.2739(15) . ?
Pd Cl2 2.2929(15) . ?
O C2 1.400(7) . ?
O C5 1.445(7) . ?
N1 C2 1.482(7) . ?
N1 C6 1.499(7) . ?
N1 C4 1.517(6) . ?
N2 C14 1.343(7) . ?
N2 C18 1.353(7) . ?
C2 C14 1.502(8) . ?
C2 H2 0.9800 . ?
C4 C7 1.514(7) . ?
C4 C5 1.548(8) . ?
C4 H4 0.9800 . ?
C5 C8 1.489(8) . ?
C5 H5 0.9800 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.374(8) . ?
C8 C13 1.395(9) . ?
C9 C10 1.390(10) . ?
C9 H9 0.9300 . ?
C10 C11 1.369(12) . ?
C10 H10 0.9300 . ?
C11 C12 1.326(12) . ?
C11 H11 0.9300 . ?
C12 C13 1.366(10) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.385(8) . ?
C15 C16 1.350(9) . ?
C15 H15 0.9300 . ?
C16 C17 1.387(11) . ?
C16 H16 0.9300 . ?
C17 C18 1.360(8) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C1A Cl3A 1.728(7) . ?
C1A Cl3C 1.746(7) . ?
C1A Cl3B 1.770(7) . ?
C1A H1A 0.9800 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 Pd N1 C2 13.4(3) . . . . ?
Cl1 Pd N1 C2 -167.3(3) . . . . ?
Cl2 Pd N1 C2 43(3) . . . . ?
N2 Pd N1 C6 132.4(4) . . . . ?
Cl1 Pd N1 C6 -48.2(4) . . . . ?
Cl2 Pd N1 C6 162(2) . . . . ?
N2 Pd N1 C4 -100.2(3) . . . . ?
Cl1 Pd N1 C4 79.1(3) . . . . ?
Cl2 Pd N1 C4 -70(3) . . . . ?
N1 Pd N2 C14 -2.0(4) . . . . ?
Cl1 Pd N2 C14 -12(3) . . . . ?
Cl2 Pd N2 C14 179.3(4) . . . . ?
N1 Pd N2 C18 174.2(5) . . . . ?
Cl1 Pd N2 C18 164(2) . . . . ?
Cl2 Pd N2 C18 -4.5(5) . . . . ?
C5 O C2 N1 7.7(6) . . . . ?
C5 O C2 C14 -118.7(5) . . . . ?
C6 N1 C2 O 90.2(5) . . . . ?
C4 N1 C2 O -25.8(5) . . . . ?
Pd N1 C2 O -147.6(3) . . . . ?
C6 N1 C2 C14 -144.3(5) . . . . ?
C4 N1 C2 C14 99.7(5) . . . . ?
Pd N1 C2 C14 -22.1(5) . . . . ?
C2 N1 C4 C7 -90.2(5) . . . . ?
C6 N1 C4 C7 155.4(5) . . . . ?
Pd N1 C4 C7 26.6(5) . . . . ?
C2 N1 C4 C5 32.4(5) . . . . ?
C6 N1 C4 C5 -82.0(5) . . . . ?
Pd N1 C4 C5 149.2(3) . . . . ?
C2 O C5 C8 141.8(5) . . . . ?
C2 O C5 C4 13.5(6) . . . . ?
C7 C4 C5 O 93.9(6) . . . . ?
N1 C4 C5 O -28.6(5) . . . . ?
C7 C4 C5 C8 -29.3(7) . . . . ?
N1 C4 C5 C8 -151.9(5) . . . . ?
O C5 C8 C9 155.6(5) . . . . ?
C4 C5 C8 C9 -84.4(7) . . . . ?
O C5 C8 C13 -24.9(7) . . . . ?
C4 C5 C8 C13 95.2(6) . . . . ?
C13 C8 C9 C10 2.7(9) . . . . ?
C5 C8 C9 C10 -177.8(6) . . . . ?
C8 C9 C10 C11 -1.0(10) . . . . ?
C9 C10 C11 C12 -1.6(11) . . . . ?
C10 C11 C12 C13 2.5(12) . . . . ?
C11 C12 C13 C8 -0.8(11) . . . . ?
C9 C8 C13 C12 -1.8(9) . . . . ?
C5 C8 C13 C12 178.6(6) . . . . ?
C18 N2 C14 C15 -2.8(8) . . . . ?
Pd N2 C14 C15 173.7(5) . . . . ?
C18 N2 C14 C2 173.1(5) . . . . ?
Pd N2 C14 C2 -10.4(6) . . . . ?
O C2 C14 N2 146.7(5) . . . . ?
N1 C2 C14 N2 22.4(7) . . . . ?
O C2 C14 C15 -37.4(7) . . . . ?
N1 C2 C14 C15 -161.7(5) . . . . ?
N2 C14 C15 C16 3.0(10) . . . . ?
C2 C14 C15 C16 -172.7(6) . . . . ?
C14 C15 C16 C17 -1.4(12) . . . . ?
C15 C16 C17 C18 -0.2(13) . . . . ?
C14 N2 C18 C17 1.1(9) . . . . ?
Pd N2 C18 C17 -174.9(5) . . . . ?
C16 C17 C18 N2 0.3(11) . . . . ?
