#------------------------------------------------------------------------------
#$Date: 2022-06-02 11:28:23 +0200 (Thu 02 de Jun de 2022) $
#$Revision: 275745 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/26/4022606.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_4022606
loop_
_publ_author_name
'Lasri, Jamal'
'Charmier, M. Adília Januário'
'Haukka, Matti'
'Pombeiro, Armando J. L.'
_publ_section_title
;
 Stereospecific Synthesis of Polysubstituted E-Olefins by Reaction
 of Acyclic Nitrones with Free and Platinum(II) Coordinated Organonitriles
;
_journal_coden_ASTM              JOCEAH
_journal_issue                   3
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              750
_journal_page_last               755
_journal_paper_doi               10.1021/jo061659b
_journal_volume                  72
_journal_year                    2007
_chemical_formula_sum            'C12 H11 N O2'
_chemical_formula_weight         201.22
_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                71.924(5)
_cell_angle_beta                 89.510(8)
_cell_angle_gamma                81.010(5)
_cell_formula_units_Z            2
_cell_length_a                   3.9990(4)
_cell_length_b                   11.1539(11)
_cell_length_c                   12.2250(10)
_cell_measurement_temperature    100(2)
_cell_volume                     511.55(8)
_computing_cell_refinement       'Denzo/Scalepack (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction        'Denzo/Scalepack (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'XP in SHELXTL v.6.12 (Bruker AXS, 2002)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_sigmaI/netI    0.0420
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            2965
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.89
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             212
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         1765
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0491
_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)+(0.0641P)²+0.2572P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1200
_refine_ls_wR_factor_ref         0.1322
_reflns_number_gt                1410
_reflns_number_total             1765
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo061659bsi20060810_121904.cif
_cod_data_source_block           z2d
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_database_code               4022606
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
C1 C 0.4858(6) 0.07321(19) 0.12754(18) 0.0323(5) Uani 1 1 d .
H1A H 0.7292 0.0702 0.1156 0.048 Uiso 1 1 calc R
H1B H 0.4302 -0.0133 0.1467 0.048 Uiso 1 1 calc R
H1C H 0.4254 0.1078 0.1909 0.048 Uiso 1 1 calc R
C2 C 0.3279(5) 0.27857(18) -0.00736(17) 0.0249(5) Uani 1 1 d .
C3 C 0.1427(5) 0.35241(18) -0.11879(16) 0.0238(5) Uani 1 1 d .
N1 N -0.1611(5) 0.22223(16) -0.21682(16) 0.0335(5) Uani 1 1 d .
C5 C 0.1481(5) 0.47909(18) -0.16121(17) 0.0243(4) Uani 1 1 d .
H5 H 0.2618 0.5126 -0.1122 0.029 Uiso 1 1 calc R
C6 C 0.0098(5) 0.57340(18) -0.26915(17) 0.0242(4) Uani 1 1 d .
C7 C -0.1471(5) 0.54636(19) -0.35919(17) 0.0272(5) Uani 1 1 d .
H7 H -0.1752 0.4610 -0.3509 0.033 Uiso 1 1 calc R
C8 C -0.2610(5) 0.64284(19) -0.45975(18) 0.0282(5) Uani 1 1 d .
H8 H -0.3654 0.6224 -0.5197 0.034 Uiso 1 1 calc R
C9 C -0.2264(5) 0.76950(18) -0.47530(17) 0.0254(5) Uani 1 1 d .
C10 C -0.0700(5) 0.79631(18) -0.38604(18) 0.0269(5) Uani 1 1 d .
H10 H -0.0434 0.8819 -0.3946 0.032 Uiso 1 1 calc R
C11 C 0.0474(5) 0.70039(18) -0.28505(17) 0.0259(5) Uani 1 1 d .
H11 H 0.1548 0.7211 -0.2258 0.031 Uiso 1 1 calc R
C12 C -0.3525(5) 0.87286(19) -0.58534(18) 0.0305(5) Uani 1 1 d .
H12A H -0.3951 0.9556 -0.5712 0.046 Uiso 1 1 calc R
H12B H -0.5632 0.8554 -0.6131 0.046 Uiso 1 1 calc R
H12C H -0.1814 0.8750 -0.6435 0.046 Uiso 1 1 calc R
C4 C -0.0238(5) 0.28056(18) -0.17431(17) 0.0259(5) Uani 1 1 d .
O1 O 0.2973(3) 0.15437(12) 0.02326(12) 0.0275(4) Uani 1 1 d .
O2 O 0.4892(4) 0.32394(13) 0.04813(12) 0.0331(4) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0399(12) 0.0234(10) 0.0296(11) -0.0028(8) -0.0026(9) -0.0045(9)
C2 0.0261(10) 0.0227(10) 0.0259(11) -0.0078(8) 0.0038(8) -0.0039(8)
C3 0.0257(10) 0.0227(10) 0.0247(11) -0.0095(8) 0.0038(8) -0.0050(8)
N1 0.0387(11) 0.0270(9) 0.0360(11) -0.0111(8) -0.0012(8) -0.0064(8)
C5 0.0261(10) 0.0242(10) 0.0247(10) -0.0106(8) 0.0035(8) -0.0046(7)
C6 0.0234(10) 0.0232(10) 0.0264(11) -0.0084(8) 0.0025(8) -0.0033(8)
C7 0.0315(11) 0.0246(10) 0.0289(11) -0.0122(8) 0.0010(9) -0.0065(8)
C8 0.0303(11) 0.0298(11) 0.0264(11) -0.0118(8) -0.0020(8) -0.0047(8)
C9 0.0233(10) 0.0270(10) 0.0258(11) -0.0086(8) 0.0019(8) -0.0027(8)
C10 0.0303(11) 0.0196(9) 0.0311(11) -0.0083(8) 0.0002(9) -0.0040(8)
C11 0.0283(10) 0.0247(10) 0.0265(11) -0.0104(8) 0.0003(8) -0.0053(8)
C12 0.0335(11) 0.0278(11) 0.0282(11) -0.0079(9) -0.0017(9) -0.0007(8)
C4 0.0283(11) 0.0216(10) 0.0270(11) -0.0066(8) 0.0030(8) -0.0040(8)
O1 0.0341(8) 0.0198(7) 0.0270(8) -0.0039(6) -0.0018(6) -0.0061(6)
O2 0.0456(9) 0.0254(7) 0.0296(8) -0.0080(6) -0.0063(7) -0.0104(6)
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 C1 H1A 109.5
O1 C1 H1B 109.5
H1A C1 H1B 109.5
O1 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
O2 C2 O1 124.03(18)
O2 C2 C3 124.37(17)
O1 C2 C3 111.59(16)
C5 C3 C4 124.99(18)
C5 C3 C2 118.80(17)
C4 C3 C2 116.19(16)
C3 C5 C6 131.20(19)
C3 C5 H5 114.4
C6 C5 H5 114.4
C11 C6 C7 117.86(17)
C11 C6 C5 116.85(18)
C7 C6 C5 125.26(17)
C8 C7 C6 120.59(18)
C8 C7 H7 119.7
C6 C7 H7 119.7
C7 C8 C9 121.60(19)
C7 C8 H8 119.2
C9 C8 H8 119.2
C10 C9 C8 117.80(18)
C10 C9 C12 121.52(18)
C8 C9 C12 120.68(18)
C11 C10 C9 121.20(18)
C11 C10 H10 119.4
C9 C10 H10 119.4
C10 C11 C6 120.93(18)
C10 C11 H11 119.5
C6 C11 H11 119.5
C9 C12 H12A 109.5
C9 C12 H12B 109.5
H12A C12 H12B 109.5
C9 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
N1 C4 C3 178.6(2)
C2 O1 C1 115.60(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.449(2)
C1 H1A 0.9800
C1 H1B 0.9800
C1 H1C 0.9800
C2 O2 1.206(2)
C2 O1 1.343(2)
C2 C3 1.488(3)
C3 C5 1.349(3)
C3 C4 1.435(3)
N1 C4 1.149(3)
C5 C6 1.457(3)
C5 H5 0.9500
C6 C11 1.401(3)
C6 C7 1.405(3)
C7 C8 1.383(3)
C7 H7 0.9500
C8 C9 1.395(3)
C8 H8 0.9500
C9 C10 1.394(3)
C9 C12 1.504(3)
C10 C11 1.387(3)
C10 H10 0.9500
C11 H11 0.9500
C12 H12A 0.9800
C12 H12B 0.9800
C12 H12C 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
O2 C2 C3 C5 -1.1(3)
O1 C2 C3 C5 179.77(16)
O2 C2 C3 C4 177.59(19)
O1 C2 C3 C4 -1.6(2)
C4 C3 C5 C6 -2.5(3)
C2 C3 C5 C6 176.06(18)
C3 C5 C6 C11 177.33(19)
C3 C5 C6 C7 -4.8(3)
C11 C6 C7 C8 -0.3(3)
C5 C6 C7 C8 -178.06(18)
C6 C7 C8 C9 -0.3(3)
C7 C8 C9 C10 0.4(3)
C7 C8 C9 C12 -179.94(19)
C8 C9 C10 C11 0.0(3)
C12 C9 C10 C11 -179.63(18)
C9 C10 C11 C6 -0.5(3)
C7 C6 C11 C10 0.7(3)
C5 C6 C11 C10 178.67(18)
C5 C3 C4 N1 -122(9)
C2 C3 C4 N1 59(9)
O2 C2 O1 C1 -2.6(3)
C3 C2 O1 C1 176.56(16)
loop_
_cod_changelog_entry_id
_cod_changelog_entry_author
_cod_changelog_entry_date
_cod_changelog_entry_text
1 'Vaitkus, Antanas' 2022-06-02T12:25:00+03:00
'Updated bibliographic information.'
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4732121
