#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/49/7204992.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_7204992
_publ_section_title
;
 4-Phenyloxazolidin-2-ones and isoindolin-1-ones: chiral auxiliaries for
 Diels--Alder reactions of N-substituted 1,3-dienes
;
_journal_issue                   1
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              69
_journal_paper_doi               10.1039/b108059h
_journal_year                    2002
_chemical_formula_sum            'C13 H13 N O2'
_chemical_formula_weight         215.24
_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   difmap
_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            4
_cell_length_a                   6.0693(6)
_cell_length_b                   8.7995(9)
_cell_length_c                   21.691(2)
_cell_measurement_temperature    153(2)
_cell_volume                     1158.4(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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      153(2)
_diffrn_measured_fraction_theta_full 0.871
_diffrn_measured_fraction_theta_max 0.871
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0374
_diffrn_reflns_av_sigmaI/netI    0.0330
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            5654
_diffrn_reflns_theta_full        28.55
_diffrn_reflns_theta_max         28.55
_diffrn_reflns_theta_min         1.88
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1.2(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     197
_refine_ls_number_reflns         2405
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0483
_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)+(0.0858P)²+0.0444P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1194
_refine_ls_wR_factor_ref         0.1306
_reflns_number_gt                2159
_reflns_number_total             2405
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b108059h.txt
_cod_data_source_block           ps5m
_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 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not_measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7204992
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
C1 C -0.2945(4) 0.5260(3) -0.17498(9) 0.0452(5) Uani 1 1 d . . .
H1A H -0.272(4) 0.640(3) -0.1888(12) 0.052(7) Uiso 1 1 d . . .
H1B H -0.163(4) 0.474(3) -0.1593(11) 0.047(6) Uiso 1 1 d . . .
C2 C -0.4822(3) 0.4566(2) -0.18615(8) 0.0353(4) Uani 1 1 d . . .
H2 H -0.596(4) 0.511(3) -0.2066(10) 0.043(6) Uiso 1 1 d . . .
C3 C -0.5279(3) 0.2985(2) -0.17195(8) 0.0316(4) Uani 1 1 d . . .
H3 H -0.415(4) 0.246(3) -0.1565(9) 0.033(5) Uiso 1 1 d . . .
C4 C -0.7199(3) 0.2343(2) -0.18453(8) 0.0308(4) Uani 1 1 d . . .
H4 H -0.840(3) 0.284(2) -0.2020(9) 0.026(5) Uiso 1 1 d . . .
N5 N -0.7714(3) 0.08209(18) -0.17344(7) 0.0322(3) Uani 1 1 d . . .
C6 C -0.9671(3) 0.0221(2) -0.19159(8) 0.0347(4) Uani 1 1 d . . .
O6 O -1.1233(2) 0.08834(18) -0.21230(7) 0.0469(4) Uani 1 1 d . . .
O7 O -0.9660(2) -0.12883(16) -0.18236(7) 0.0428(4) Uani 1 1 d . . .
C8 C -0.7466(4) -0.1770(3) -0.16542(11) 0.0479(6) Uani 1 1 d . . .
H8A H -0.675(6) -0.229(4) -0.2031(16) 0.088(11) Uiso 1 1 d . . .
H8B H -0.769(4) -0.228(3) -0.1292(12) 0.045(6) Uiso 1 1 d . . .
C9 C -0.6156(3) -0.0315(2) -0.15183(8) 0.0322(4) Uani 1 1 d . . .
H9A H -0.473(4) -0.028(3) -0.1773(10) 0.040(5) Uiso 1 1 d . . .
C10 C -0.5478(3) -0.0127(2) -0.08502(7) 0.0339(4) Uani 1 1 d . . .
C11 C -0.6720(4) 0.0688(3) -0.04339(9) 0.0487(6) Uani 1 1 d . . .
H11 H -0.805(4) 0.110(3) -0.0567(11) 0.045(6) Uiso 1 1 d . . .
C12 C -0.6000(6) 0.0838(4) 0.01748(10) 0.0696(8) Uani 1 1 d . . .
H12 H -0.690(5) 0.149(4) 0.0445(14) 0.065(8) Uiso 1 1 d . . .
C13 C -0.4102(5) 0.0145(3) 0.03647(10) 0.0646(7) Uani 1 1 d . . .
H13 H -0.358(5) 0.024(4) 0.0812(15) 0.076(9) Uiso 1 1 d . . .
C14 C -0.2855(5) -0.0671(4) -0.00461(10) 0.0604(7) Uani 1 1 d . . .
H14 H -0.155(5) -0.113(4) 0.0035(13) 0.065(9) Uiso 1 1 d . . .
C15 C -0.3553(3) -0.0809(3) -0.06553(9) 0.0469(5) Uani 1 1 d . . .
H15 H -0.276(5) -0.148(4) -0.0923(14) 0.078(10) Uiso 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'
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 C2 C3 124.86(19) . . ?
C4 C3 C2 122.26(19) . . ?
C3 C4 N5 124.84(18) . . ?
C6 N5 C4 121.24(16) . . ?
C6 N5 C9 113.27(16) . . ?
C4 N5 C9 124.73(16) . . ?
O6 C6 O7 122.66(18) . . ?
O6 C6 N5 127.66(19) . . ?
O7 C6 N5 109.67(17) . . ?
C6 O7 C8 109.43(15) . . ?
O7 C8 C9 106.32(17) . . ?
N5 C9 C10 114.19(15) . . ?
N5 C9 C8 100.08(15) . . ?
C10 C9 C8 114.54(16) . . ?
C11 C10 C15 119.27(18) . . ?
C11 C10 C9 122.35(17) . . ?
C15 C10 C9 118.38(17) . . ?
C10 C11 C12 119.8(2) . . ?
C13 C12 C11 120.4(2) . . ?
C12 C13 C14 120.2(2) . . ?
C13 C14 C15 119.6(3) . . ?
C10 C15 C14 120.7(2) . . ?
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
C1 C2 1.315(3) . ?
C2 C3 1.451(3) . ?
C3 C4 1.324(3) . ?
C4 N5 1.396(3) . ?
N5 C6 1.358(3) . ?
N5 C9 1.454(2) . ?
C6 O6 1.200(2) . ?
C6 O7 1.343(3) . ?
O7 C8 1.445(3) . ?
C8 C9 1.535(3) . ?
C9 C10 1.516(2) . ?
C10 C11 1.378(3) . ?
C10 C15 1.380(3) . ?
C11 C12 1.397(3) . ?
C12 C13 1.367(4) . ?
C13 C14 1.372(4) . ?
C14 C15 1.393(3) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9032162
