#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/16/7151651.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_7151651
loop_
_publ_author_name
'Chen, Guofei'
'Fu, Chunling'
'Ma, Shengming'
_publ_section_title
;
 A novel synthesis of oxazolidine-2,4-diones via an efficient fixation
 of CO2 with 3-aryl-2-alkynamides.
;
_journal_issue                   1
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              105
_journal_page_last               110
_journal_paper_doi               10.1039/C0OB00550A
_journal_volume                  9
_journal_year                    2011
_chemical_formula_sum            'C17 H13 N O3'
_chemical_formula_weight         279.28
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 106.517(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.4285(4)
_cell_length_b                   31.4664(18)
_cell_length_c                   7.0702(4)
_cell_measurement_temperature    173(2)
_cell_volume                     1371.16(14)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0299
_diffrn_reflns_av_sigmaI/netI    0.0185
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            15862
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.59
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.795411
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.505
_exptl_crystal_size_mid          0.121
_exptl_crystal_size_min          0.077
_refine_diff_density_max         0.382
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2426
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0411
_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)+(0.0416P)²+0.6758P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0989
_refine_ls_wR_factor_ref         0.1038
_reflns_number_gt                2086
_reflns_number_total             2426
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            C0OB00550A.TXT
_cod_data_source_block           z
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7151651
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
N1 N 0.2001(2) 0.10956(4) 0.17480(19) 0.0300(3) Uani 1 1 d . . .
O1 O -0.1567(2) 0.13115(4) 0.05164(19) 0.0451(3) Uani 1 1 d . . .
O2 O 0.49464(19) 0.06670(4) 0.31777(18) 0.0395(3) Uani 1 1 d . . .
O3 O -0.07127(18) 0.06384(4) 0.15223(16) 0.0340(3) Uani 1 1 d . . .
C1 C 0.0385(3) -0.07197(5) 0.3451(2) 0.0329(4) Uani 1 1 d . . .
H1A H 0.1888 -0.0781 0.3957 0.039 Uiso 1 1 calc R . .
C2 C -0.1124(3) -0.10362(6) 0.3351(3) 0.0375(4) Uani 1 1 d . . .
H2A H -0.0651 -0.1314 0.3794 0.045 Uiso 1 1 calc R . .
C3 C -0.3295(3) -0.09543(6) 0.2620(2) 0.0368(4) Uani 1 1 d . . .
H3A H -0.4323 -0.1175 0.2561 0.044 Uiso 1 1 calc R . .
C4 C -0.3985(3) -0.05528(6) 0.1973(2) 0.0360(4) Uani 1 1 d . . .
H4A H -0.5493 -0.0498 0.1450 0.043 Uiso 1 1 calc R . .
C5 C -0.2515(3) -0.02289(5) 0.2073(2) 0.0327(4) Uani 1 1 d . . .
H5A H -0.3014 0.0048 0.1640 0.039 Uiso 1 1 calc R . .
C6 C -0.0285(3) -0.03074(5) 0.2811(2) 0.0292(4) Uani 1 1 d U . .
C7 C 0.1368(3) 0.00169(5) 0.2945(2) 0.0304(4) Uani 1 1 d U . .
H7A H 0.2810 -0.0077 0.3541 0.036 Uiso 1 1 calc R . .
C8 C 0.1214(3) 0.04235(5) 0.2377(2) 0.0301(4) Uani 1 1 d . . .
C9 C 0.3014(3) 0.07201(5) 0.2536(2) 0.0307(4) Uani 1 1 d . . .
C10 C -0.0212(3) 0.10496(5) 0.1188(2) 0.0326(4) Uani 1 1 d . . .
C11 C 0.3135(3) 0.14893(6) 0.1559(2) 0.0357(4) Uani 1 1 d . . .
H11A H 0.2186 0.1667 0.0505 0.043 Uiso 1 1 calc R . .
H11B H 0.4457 0.1420 0.1167 0.043 Uiso 1 1 calc R . .
C12 C 0.3764(3) 0.17383(5) 0.3459(2) 0.0342(4) Uani 1 1 d . . .
C13 C 0.5893(3) 0.17374(6) 0.4630(3) 0.0434(5) Uani 1 1 d . . .
H13A H 0.6968 0.1587 0.4217 0.052 Uiso 1 1 calc R . .
C14 C 0.6458(4) 0.19568(6) 0.6411(3) 0.0557(6) Uani 1 1 d . . .
H14A H 0.7919 0.1955 0.7216 0.067 Uiso 1 1 calc R . .
C15 C 0.4907(4) 0.21772(6) 0.7012(3) 0.0587(6) Uani 1 1 d . . .
H15A H 0.5297 0.2326 0.8231 0.070 Uiso 1 1 calc R . .
C16 C 0.2798(4) 0.21811(6) 0.5848(3) 0.0556(6) Uani 1 1 d . . .
H16A H 0.1730 0.2335 0.6260 0.067 Uiso 1 1 calc R . .
C17 C 0.2218(3) 0.19625(6) 0.4075(3) 0.0425(5) Uani 1 1 d . . .
H17A H 0.0754 0.1966 0.3278 0.051 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'
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
C10 N1 C9 110.87(14) . . ?
C10 N1 C11 124.49(14) . . ?
C9 N1 C11 124.64(14) . . ?
C10 O3 C8 108.08(13) . . ?
C2 C1 C6 120.34(16) . . ?
C2 C1 H1A 119.8 . . ?
C6 C1 H1A 119.8 . . ?
C3 C2 C1 120.73(16) . . ?
C3 C2 H2A 119.6 . . ?
C1 C2 H2A 119.6 . . ?
C2 C3 C4 119.82(16) . . ?
C2 C3 H3A 120.1 . . ?
C4 C3 H3A 120.1 . . ?
C3 C4 C5 120.76(16) . . ?
C3 C4 H4A 119.6 . . ?
C5 C4 H4A 119.6 . . ?
C4 C5 C6 120.19(16) . . ?
C4 C5 H5A 119.9 . . ?
C6 C5 H5A 119.9 . . ?
C5 C6 C1 118.16(15) . . ?
C5 C6 C7 123.44(15) . . ?
C1 C6 C7 118.40(15) . . ?
C8 C7 C6 131.36(16) . . ?
C8 C7 H7A 114.3 . . ?
C6 C7 H7A 114.3 . . ?
C7 C8 O3 125.25(15) . . ?
C7 C8 C9 126.68(16) . . ?
O3 C8 C9 108.07(13) . . ?
O2 C9 N1 125.79(16) . . ?
O2 C9 C8 130.26(16) . . ?
N1 C9 C8 103.95(14) . . ?
O1 C10 O3 122.64(16) . . ?
O1 C10 N1 128.38(16) . . ?
O3 C10 N1 108.99(14) . . ?
N1 C11 C12 111.89(13) . . ?
N1 C11 H11A 109.2 . . ?
C12 C11 H11A 109.2 . . ?
N1 C11 H11B 109.2 . . ?
C12 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C13 C12 C17 119.26(17) . . ?
C13 C12 C11 120.06(16) . . ?
C17 C12 C11 120.66(17) . . ?
C12 C13 C14 119.99(19) . . ?
C12 C13 H13A 120.0 . . ?
C14 C13 H13A 120.0 . . ?
C15 C14 C13 120.2(2) . . ?
C15 C14 H14A 119.9 . . ?
C13 C14 H14A 119.9 . . ?
C16 C15 C14 119.90(19) . . ?
C16 C15 H15A 120.1 . . ?
C14 C15 H15A 120.1 . . ?
C15 C16 C17 120.3(2) . . ?
C15 C16 H16A 119.9 . . ?
C17 C16 H16A 119.9 . . ?
C16 C17 C12 120.3(2) . . ?
C16 C17 H17A 119.8 . . ?
C12 C17 H17A 119.8 . . ?
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
N1 C10 1.371(2) . ?
N1 C9 1.387(2) . ?
N1 C11 1.463(2) . ?
O1 C10 1.195(2) . ?
O2 C9 1.207(2) . ?
O3 C10 1.370(2) . ?
O3 C8 1.390(2) . ?
C1 C2 1.378(2) . ?
C1 C6 1.401(2) . ?
C1 H1A 0.9500 . ?
C2 C3 1.368(3) . ?
C2 H2A 0.9500 . ?
C3 C4 1.374(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.378(2) . ?
C4 H4A 0.9500 . ?
C5 C6 1.400(2) . ?
C5 H5A 0.9500 . ?
C6 C7 1.457(2) . ?
C7 C8 1.336(2) . ?
C7 H7A 0.9500 . ?
C8 C9 1.466(2) . ?
C11 C12 1.508(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.383(3) . ?
C12 C17 1.386(3) . ?
C13 C14 1.391(3) . ?
C13 H13A 0.9500 . ?
C14 C15 1.377(3) . ?
C14 H14A 0.9500 . ?
C15 C16 1.372(3) . ?
C15 H15A 0.9500 . ?
C16 C17 1.385(3) . ?
C16 H16A 0.9500 . ?
C17 H17A 0.9500 . ?
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
C6 C1 C2 C3 0.3(2) . . . . ?
C1 C2 C3 C4 0.2(3) . . . . ?
C2 C3 C4 C5 -0.8(2) . . . . ?
C3 C4 C5 C6 1.0(2) . . . . ?
C4 C5 C6 C1 -0.6(2) . . . . ?
C4 C5 C6 C7 179.35(14) . . . . ?
C2 C1 C6 C5 0.0(2) . . . . ?
C2 C1 C6 C7 -179.98(14) . . . . ?
C5 C6 C7 C8 -3.2(3) . . . . ?
C1 C6 C7 C8 176.69(16) . . . . ?
C6 C7 C8 O3 1.9(3) . . . . ?
C6 C7 C8 C9 -178.06(15) . . . . ?
C10 O3 C8 C7 178.74(15) . . . . ?
C10 O3 C8 C9 -1.33(16) . . . . ?
C10 N1 C9 O2 -178.88(15) . . . . ?
C11 N1 C9 O2 0.5(2) . . . . ?
C10 N1 C9 C8 1.36(16) . . . . ?
C11 N1 C9 C8 -179.25(13) . . . . ?
C7 C8 C9 O2 0.2(3) . . . . ?
O3 C8 C9 O2 -179.75(15) . . . . ?
C7 C8 C9 N1 179.93(15) . . . . ?
O3 C8 C9 N1 0.00(16) . . . . ?
C8 O3 C10 O1 -177.60(15) . . . . ?
C8 O3 C10 N1 2.18(16) . . . . ?
C9 N1 C10 O1 177.51(17) . . . . ?
C11 N1 C10 O1 -1.9(3) . . . . ?
C9 N1 C10 O3 -2.26(17) . . . . ?
C11 N1 C10 O3 178.35(13) . . . . ?
C10 N1 C11 C12 97.09(18) . . . . ?
C9 N1 C11 C12 -82.22(19) . . . . ?
N1 C11 C12 C13 103.75(18) . . . . ?
N1 C11 C12 C17 -74.8(2) . . . . ?
C17 C12 C13 C14 0.6(3) . . . . ?
C11 C12 C13 C14 -178.07(17) . . . . ?
C12 C13 C14 C15 -0.3(3) . . . . ?
C13 C14 C15 C16 -0.1(3) . . . . ?
C14 C15 C16 C17 0.3(3) . . . . ?
C15 C16 C17 C12 -0.1(3) . . . . ?
C13 C12 C17 C16 -0.3(3) . . . . ?
C11 C12 C17 C16 178.27(16) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 29434818
2 PubChem 50917911
