#------------------------------------------------------------------------------
#$Date: 2016-03-22 23:46:46 +0200 (Tue, 22 Mar 2016) $
#$Revision: 179077 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/39/4303923.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_4303923
loop_
_publ_author_name
'Sonia Nieto'
'Palmira Arnau'
'Elena Serrano'
'Rafael Navarro'
'Tatiana Soler'
'Carlos Cativiela'
'Esteban P. Urriolabeitia'
_publ_contact_author_address
'ICMA, CSIC-Universidad de Zaragoza, Plaza S. Francisco, 50009 Zaragoza (Spain)'
_publ_contact_author_email       esteban@unizar.es
_publ_contact_author_fax         (+34)976761187
_publ_contact_author_name        'Esteban P. Urriolabeitia'
_publ_contact_author_phone       (+34)976762302
_publ_section_title
;
Functionalization of Methyl (R)-Phenylglycinate Through Orthopalladation:
C-Hal, C-O, C-N, and C-C Bond Coupling
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              11963
_journal_page_last               11975
_journal_paper_doi               10.1021/ic901941s
_journal_volume                  48
_journal_year                    2009
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C18 H20 Cl2 N2 O4 Pd2'
_chemical_formula_sum            'C18 H20 Cl2 N2 O4 Pd2'
_chemical_formula_weight         612.06
_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                   4.97020(10)
_cell_length_b                   15.6329(3)
_cell_length_c                   26.4781(5)
_cell_measurement_reflns_used    7584
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      28.6597
_cell_measurement_theta_min      3.0668
_cell_volume                     2057.31(7)
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.19 (release 28-02-2008 CrysAlis171 .NET)
(compiled Feb 28 2008,12:10:31)
;
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.19 (release 28-02-2008 CrysAlis171 .NET)
(compiled Feb 28 2008,12:10:31)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.19 (release 28-02-2008 CrysAlis171 .NET)
(compiled Feb 28 2008,12:10:31)
;
_computing_molecular_graphics
;
SHELXTL  Rel. 6.12/V (Sheldrick, Acta Cryst. 2008, A64, 112-122)
;
_computing_publication_material
;
SHELX-97 (Sheldrick, Acta Cryst. 2008, A64, 112-122)' 
;
_computing_structure_refinement
;
SHELXL-97 (Sheldrick, Acta Cryst. 2008, A64, 112-122) 
;
_computing_structure_solution
;
SHELXL-97 (Sheldrick, Acta Cryst. 2008, A64, 112-122) 
;
_diffrn_ambient_temperature      150(1)
_diffrn_detector_area_resol_mean 16.3990
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur2'
_diffrn_measurement_method       'ω and φ scans'
_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  0.0301
_diffrn_reflns_av_sigmaI/netI    0.0361
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            12132
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.72
_exptl_absorpt_coefficient_mu    2.035
_exptl_absorpt_correction_T_max  0.8707
_exptl_absorpt_correction_T_min  0.8337
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.19 (release 28-02-2008 CrysAlis171 .NET)
(compiled Feb 28 2008,12:10:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.976
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.526
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.074
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3600
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0288
_refine_ls_R_factor_gt           0.0235
_refine_ls_shift/su_max          0.036
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0205P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0459
_refine_ls_wR_factor_ref         0.0467
_reflns_number_gt                3198
_reflns_number_total             3600
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ic901941s_si_002_2.cif
_cod_data_source_block           '__1'
_cod_database_code               4303923
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
Pd1 Pd 0.51590(8) 0.062780(18) 0.901233(10) 0.02112(9) Uani 1 1 d . . .
Pd2 Pd 1.01877(8) 0.046229(17) 0.990797(10) 0.01881(8) Uani 1 1 d . . .
Cl2 Cl 0.7881(2) 0.16816(6) 0.94918(4) 0.0217(2) Uani 1 1 d . . .
Cl1 Cl 0.7440(2) -0.04492(7) 0.94429(4) 0.0262(2) Uani 1 1 d . . .
O1 O 0.5584(7) 0.19546(17) 0.78301(10) 0.0305(8) Uani 1 1 d . . .
O2 O 0.2739(7) 0.12608(18) 0.73250(11) 0.0340(8) Uani 1 1 d . . .
O3 O 0.9939(8) 0.15672(15) 1.11282(8) 0.0259(6) Uani 1 1 d . . .
O4 O 1.2347(6) 0.06777(18) 1.16046(10) 0.0328(8) Uani 1 1 d . . .
N1 N 0.2916(7) 0.1565(2) 0.86735(11) 0.0234(9) Uani 1 1 d . . .
H1A H 0.1819 0.1557 0.8927 0.028 Uiso 1 1 d R . .
H1B H 0.3860 0.2057 0.8657 0.028 Uiso 1 1 d R . .
N2 N 1.2746(7) 0.12424(19) 1.02900(11) 0.0188(8) Uani 1 1 d . . .
H2A H 1.2365 0.1706 1.0447 0.023 Uiso 1 1 d R . .
H2B H 1.4704 0.1364 1.0118 0.023 Uiso 1 1 d R . .
C1 C 0.2926(9) -0.0117(3) 0.85860(15) 0.0223(10) Uani 1 1 d . . .
C2 C 0.2706(10) -0.1005(3) 0.86233(16) 0.0290(11) Uani 1 1 d . . .
H2 H 0.3797 -0.1313 0.8855 0.035 Uiso 1 1 calc R . .
C3 C 0.0883(9) -0.1432(3) 0.83194(16) 0.0318(12) Uani 1 1 d . . .
H3 H 0.0712 -0.2035 0.8350 0.038 Uiso 1 1 calc R . .
C4 C -0.0666(10) -0.1011(3) 0.79789(16) 0.0333(13) Uani 1 1 d . . .
H4A H -0.1891 -0.1318 0.7772 0.040 Uiso 1 1 calc R . .
C5 C -0.0459(11) -0.0136(3) 0.79335(15) 0.0313(13) Uani 1 1 d . . .
H5 H -0.1572 0.0159 0.7700 0.038 Uiso 1 1 calc R . .
C6 C 0.1363(9) 0.0318(3) 0.82271(15) 0.0224(10) Uani 1 1 d . . .
C7 C 0.1718(9) 0.1274(3) 0.81916(15) 0.0231(10) Uani 1 1 d . . .
H7 H -0.0075 0.1553 0.8143 0.028 Uiso 1 1 calc R . .
C8 C 0.3600(9) 0.1541(3) 0.77695(16) 0.0225(11) Uani 1 1 d . . .
C9 C 0.4403(11) 0.1495(3) 0.69104(15) 0.0374(14) Uani 1 1 d . . .
H9A H 0.3654 0.1259 0.6598 0.056 Uiso 1 1 calc R . .
H9B H 0.6220 0.1268 0.6963 0.056 Uiso 1 1 calc R . .
H9C H 0.4482 0.2120 0.6885 0.056 Uiso 1 1 calc R . .
C10 C 1.2082(9) -0.0418(3) 1.02933(15) 0.0224(10) Uani 1 1 d . . .
C11 C 1.1964(10) -0.1296(3) 1.02192(17) 0.0336(12) Uani 1 1 d . . .
H11 H 1.0757 -0.1527 0.9977 0.040 Uiso 1 1 calc R . .
C12 C 1.3601(10) -0.1837(3) 1.04974(19) 0.0410(14) Uani 1 1 d . . .
H12 H 1.3455 -0.2437 1.0450 0.049 Uiso 1 1 calc R . .
C13 C 1.5402(12) -0.1531(3) 1.08346(17) 0.0388(13) Uani 1 1 d . . .
H13 H 1.6591 -0.1910 1.1005 0.047 Uiso 1 1 calc R . .
C14 C 1.5498(9) -0.0655(3) 1.09305(15) 0.0307(11) Uani 1 1 d . . .
H14 H 1.6712 -0.0433 1.1174 0.037 Uiso 1 1 calc R . .
C15 C 1.3821(8) -0.0116(2) 1.06691(15) 0.0197(10) Uani 1 1 d . . .
C16 C 1.3714(9) 0.0845(2) 1.07616(15) 0.0201(10) Uani 1 1 d . . .
H16 H 1.5550 0.1064 1.0846 0.024 Uiso 1 1 calc R . .
C17 C 1.1762(9) 0.1078(2) 1.11748(15) 0.0196(10) Uani 1 1 d . . .
C18 C 1.0581(11) 0.0851(3) 1.20202(14) 0.0364(14) Uani 1 1 d . . .
H18A H 1.1066 0.0486 1.2307 0.055 Uiso 1 1 calc R . .
H18B H 0.8720 0.0734 1.1919 0.055 Uiso 1 1 calc R . .
H18C H 1.0751 0.1453 1.2119 0.055 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'
Cl Cl 0.1484 0.1585 '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'
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
C1 Pd1 N1 82.22(15) . . ?
C1 Pd1 Cl1 97.36(13) . . ?
N1 Pd1 Cl1 175.55(10) . . ?
C1 Pd1 Cl2 174.42(12) . . ?
N1 Pd1 Cl2 92.63(10) . . ?
Cl1 Pd1 Cl2 87.94(4) . . ?
C10 Pd2 N2 82.04(15) . . ?
C10 Pd2 Cl1 97.33(13) . . ?
N2 Pd2 Cl1 177.06(10) . . ?
C10 Pd2 Cl2 174.12(12) . . ?
N2 Pd2 Cl2 92.81(9) . . ?
Cl1 Pd2 Cl2 87.95(4) . . ?
Pd1 Cl2 Pd2 88.23(3) . . ?
Pd2 Cl1 Pd1 95.86(4) . . ?
C8 O2 C9 114.3(4) . . ?
C17 O4 C18 115.7(3) . . ?
C7 N1 Pd1 112.2(2) . . ?
C7 N1 H1A 114.2 . . ?
Pd1 N1 H1A 89.6 . . ?
C7 N1 H1B 115.4 . . ?
Pd1 N1 H1B 110.4 . . ?
H1A N1 H1B 112.3 . . ?
C16 N2 Pd2 111.9(2) . . ?
C16 N2 H2A 91.1 . . ?
Pd2 N2 H2A 127.7 . . ?
C16 N2 H2B 97.8 . . ?
Pd2 N2 H2B 117.0 . . ?
H2A N2 H2B 104.6 . . ?
C2 C1 C6 119.1(4) . . ?
C2 C1 Pd1 126.3(4) . . ?
C6 C1 Pd1 114.5(3) . . ?
C3 C2 C1 119.4(5) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C4 C3 C2 121.6(4) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C5 119.9(5) . . ?
C3 C4 H4A 120.0 . . ?
C5 C4 H4A 120.0 . . ?
C4 C5 C6 120.5(5) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 119.5(4) . . ?
C5 C6 C7 123.2(4) . . ?
C1 C6 C7 117.2(4) . . ?
N1 C7 C8 107.6(3) . . ?
N1 C7 C6 107.3(3) . . ?
C8 C7 C6 113.0(3) . . ?
N1 C7 H7 109.6 . . ?
C8 C7 H7 109.6 . . ?
C6 C7 H7 109.6 . . ?
O1 C8 O2 124.5(4) . . ?
O1 C8 C7 124.1(4) . . ?
O2 C8 C7 111.4(4) . . ?
O2 C9 H9A 109.5 . . ?
O2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C15 117.4(4) . . ?
C11 C10 Pd2 127.0(4) . . ?
C15 C10 Pd2 115.5(3) . . ?
C12 C11 C10 120.2(5) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C13 C12 C11 121.7(4) . . ?
C13 C12 H12 119.2 . . ?
C11 C12 H12 119.2 . . ?
C12 C13 C14 119.3(5) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
C15 C14 C13 119.4(4) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C14 C15 C10 121.8(4) . . ?
C14 C15 C16 123.1(4) . . ?
C10 C15 C16 115.2(4) . . ?
N2 C16 C17 107.6(3) . . ?
N2 C16 C15 106.9(3) . . ?
C17 C16 C15 112.2(3) . . ?
N2 C16 H16 110.0 . . ?
C17 C16 H16 110.0 . . ?
C15 C16 H16 110.0 . . ?
O3 C17 O4 123.8(4) . . ?
O3 C17 C16 124.7(4) . . ?
O4 C17 C16 111.5(3) . . ?
O4 C18 H18A 109.5 . . ?
O4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
Pd1 C1 1.965(4) . ?
Pd1 N1 2.048(3) . ?
Pd1 Cl1 2.3279(11) . ?
Pd1 Cl2 2.4811(11) . ?
Pd2 C10 1.955(4) . ?
Pd2 N2 2.031(3) . ?
Pd2 Cl1 2.3264(11) . ?
Pd2 Cl2 2.4824(11) . ?
O1 C8 1.190(5) . ?
O2 C8 1.327(5) . ?
O2 C9 1.423(5) . ?
O3 C17 1.193(5) . ?
O4 C17 1.331(4) . ?
O4 C18 1.433(5) . ?
N1 C7 1.480(5) . ?
N1 H1A 0.8642 . ?
N1 H1B 0.9018 . ?
N2 C16 1.476(5) . ?
N2 H2A 0.8568 . ?
N2 H2B 1.0910 . ?
C1 C2 1.396(5) . ?
C1 C6 1.403(6) . ?
C2 C3 1.384(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.356(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.376(5) . ?
C4 H4A 0.9500 . ?
C5 C6 1.389(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.508(5) . ?
C7 C8 1.516(6) . ?
C7 H7 1.0000 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.387(5) . ?
C10 C15 1.400(6) . ?
C11 C12 1.385(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.351(7) . ?
C12 H12 0.9500 . ?
C13 C14 1.394(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.372(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.523(5) . ?
C16 C17 1.507(6) . ?
C16 H16 1.0000 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
