#------------------------------------------------------------------------------
#$Date: 2016-03-22 23:46:46 +0200 (Tue, 22 Mar 2016) $
#$Revision: 179077 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/39/4303925.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_4303925
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_formula_sum            'C10 H9 N O3'
_chemical_formula_weight         191.18
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                95.711(5)
_cell_angle_beta                 93.853(4)
_cell_angle_gamma                101.686(4)
_cell_formula_units_Z            2
_cell_length_a                   5.9865(2)
_cell_length_b                   7.4403(4)
_cell_length_c                   10.3211(6)
_cell_measurement_reflns_used    2390
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.0735
_cell_measurement_theta_min      3.2551
_cell_volume                     446.15(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0482
_diffrn_reflns_av_sigmaI/netI    0.0639
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7242
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.81
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.9979
_exptl_absorpt_correction_T_min  0.9811
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             200
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.871
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1569
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.871
_refine_ls_R_factor_all          0.0729
_refine_ls_R_factor_gt           0.0374
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0403P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0712
_refine_ls_wR_factor_ref         0.0769
_reflns_number_gt                990
_reflns_number_total             1569
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic901941s_si_002_4.cif
_cod_data_source_block           '__5'
_cod_database_code               4303925
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
O1 O 0.26066(19) 0.69165(16) 0.52708(12) 0.0278(3) Uani 1 1 d . . .
O2 O -0.2164(2) 0.6176(2) 0.87004(14) 0.0444(4) Uani 1 1 d . . .
O3 O -0.4708(2) 0.79558(17) 0.84080(12) 0.0345(4) Uani 1 1 d . . .
N1 N -0.0853(2) 0.66599(19) 0.61493(14) 0.0254(4) Uani 1 1 d . . .
H1A H -0.1328 0.5459 0.5950 0.031 Uiso 1 1 calc R . .
C1 C 0.1408(3) 0.9522(2) 0.64386(16) 0.0208(4) Uani 1 1 d . . .
C2 C 0.3170(3) 1.1034(2) 0.64161(17) 0.0266(5) Uani 1 1 d . . .
H2A H 0.4538 1.0914 0.6031 0.032 Uiso 1 1 calc R . .
C3 C 0.2875(3) 1.2727(3) 0.69735(19) 0.0319(5) Uani 1 1 d . . .
H3A H 0.4055 1.3792 0.6966 0.038 Uiso 1 1 calc R . .
C4 C 0.0879(3) 1.2894(3) 0.75443(19) 0.0327(5) Uani 1 1 d . . .
H4A H 0.0719 1.4070 0.7930 0.039 Uiso 1 1 calc R . .
C5 C -0.0875(3) 1.1374(3) 0.75577(18) 0.0282(5) Uani 1 1 d . . .
H5A H -0.2239 1.1487 0.7949 0.034 Uiso 1 1 calc R . .
C6 C -0.0591(3) 0.9686(2) 0.69874(17) 0.0225(4) Uani 1 1 d . . .
C7 C -0.2212(3) 0.7813(2) 0.67933(17) 0.0227(4) Uani 1 1 d . . .
H7A H -0.3581 0.7858 0.6196 0.027 Uiso 1 1 calc R . .
C8 C -0.2971(3) 0.7191(3) 0.80739(19) 0.0252(5) Uani 1 1 d . . .
C9 C 0.1198(3) 0.7580(2) 0.58809(17) 0.0220(4) Uani 1 1 d . . .
C10 C -0.5650(3) 0.7511(3) 0.9620(2) 0.0441(6) Uani 1 1 d . . .
H10A H -0.7029 0.8017 0.9710 0.066 Uiso 1 1 calc R . .
H10B H -0.4513 0.8050 1.0357 0.066 Uiso 1 1 calc R . .
H10C H -0.6045 0.6167 0.9616 0.066 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'
O O 0.0106 0.0060 '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'
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
C8 O3 C10 116.69(14) . . ?
C9 N1 C7 114.05(14) . . ?
C9 N1 H1A 123.0 . . ?
C7 N1 H1A 123.0 . . ?
C6 C1 C2 121.53(17) . . ?
C6 C1 C9 108.65(15) . . ?
C2 C1 C9 129.76(16) . . ?
C1 C2 C3 117.66(17) . . ?
C1 C2 H2A 121.2 . . ?
C3 C2 H2A 121.2 . . ?
C2 C3 C4 121.01(18) . . ?
C2 C3 H3A 119.5 . . ?
C4 C3 H3A 119.5 . . ?
C5 C4 C3 120.82(18) . . ?
C5 C4 H4A 119.6 . . ?
C3 C4 H4A 119.6 . . ?
C4 C5 C6 118.18(17) . . ?
C4 C5 H5A 120.9 . . ?
C6 C5 H5A 120.9 . . ?
C1 C6 C5 120.77(17) . . ?
C1 C6 C7 108.57(15) . . ?
C5 C6 C7 130.63(16) . . ?
N1 C7 C8 113.32(14) . . ?
N1 C7 C6 102.10(13) . . ?
C8 C7 C6 111.96(15) . . ?
N1 C7 H7A 109.7 . . ?
C8 C7 H7A 109.7 . . ?
C6 C7 H7A 109.7 . . ?
O2 C8 O3 124.52(17) . . ?
O2 C8 C7 126.26(16) . . ?
O3 C8 C7 109.22(16) . . ?
O1 C9 N1 126.03(16) . . ?
O1 C9 C1 127.46(15) . . ?
N1 C9 C1 106.50(15) . . ?
O3 C10 H10A 109.5 . . ?
O3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 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
O1 C9 1.2367(19) . ?
O2 C8 1.193(2) . ?
O3 C8 1.332(2) . ?
O3 C10 1.447(2) . ?
N1 C9 1.340(2) . ?
N1 C7 1.443(2) . ?
N1 H1A 0.8800 . ?
C1 C6 1.380(2) . ?
C1 C2 1.381(2) . ?
C1 C9 1.478(2) . ?
C2 C3 1.381(2) . ?
C2 H2A 0.9500 . ?
C3 C4 1.390(2) . ?
C3 H3A 0.9500 . ?
C4 C5 1.380(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.381(2) . ?
C5 H5A 0.9500 . ?
C6 C7 1.515(2) . ?
C7 C8 1.512(2) . ?
C7 H7A 1.0000 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
