#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/22/2212292.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2212292
loop_
_publ_author_name
'Parvez, Masood'
'Mehrdad, Morteza'
'Sureni, Hossein'
'Heydari, Akbar'
'Jadidi, Khosrow'
_publ_section_title
;An unexpected N-substituted oxindole:
 1-(3,3,5-trimethyl-2-phenyl-1,2-oxazolidin-5-yl)-1H-indol-3(2H)-one
;
_journal_coeditor_code           LH2292
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o877
_journal_page_last               o878
_journal_paper_doi               10.1107/S1600536807002097
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C20 H22 N2 O2'
_chemical_formula_moiety         'C20 H22 N2 O2'
_chemical_formula_sum            'C20 H22 N2 O2'
_chemical_formula_weight         322.40
_chemical_name_systematic
;
1-(3,3,5-trimethyl-2-phenyl-1,2-oxazolidin-5-yl)-1H-indol-3(2H)-one
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 98.554(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.321(3)
_cell_length_b                   14.446(4)
_cell_length_c                   11.378(4)
_cell_measurement_reflns_used    6053
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.5
_cell_volume                     1677.6(9)
_computing_cell_refinement       'DENZO (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Hooft, 1998)'
_computing_data_reduction        'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SAPI91 (Fan, 1991)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'ω and φ'
_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  0.025
_diffrn_reflns_av_sigmaI/netI    0.056
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6053
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         3.5
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SORTAV; Blessing, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.20
_refine_diff_density_min         -0.21
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.02
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3825
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.02
_refine_ls_R_factor_all          0.075
_refine_ls_R_factor_gt           0.042
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.00
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.052P)²+0.104P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.094
_refine_ls_wR_factor_ref         0.108
_reflns_number_gt                2632
_reflns_number_total             3825
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh2292.cif
_cod_data_source_block           4a
_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.

'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (8
times).

'_geom_angle_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (7 times).

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

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.

'_geom_bond_publ_flag' value 'Y' changed to 'y'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (8
times).

'_geom_angle_publ_flag' value 'Y' changed to 'y' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29 (7 times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2212292
_cod_database_fobs_code          2212292
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
O O1 0.32076(8) 0.06343(6) -0.02365(7) 0.0251(2) Uani d . 1
O O2 0.11403(9) 0.04877(7) -0.37098(8) 0.0343(3) Uani d . 1
N N1 0.20768(9) 0.06345(7) 0.04153(9) 0.0226(3) Uani d . 1
N N2 0.22364(10) -0.01500(8) -0.19824(9) 0.0244(3) Uani d . 1
C C1 0.26463(12) 0.07637(9) -0.14353(11) 0.0241(3) Uani d . 1
C C2 0.14409(12) 0.13848(10) -0.13813(12) 0.0273(3) Uani d . 1
H H2A 0.1544 0.1989 -0.1767 0.033 Uiso calc R 1
H H2B 0.0633 0.1083 -0.1782 0.033 Uiso calc R 1
C C3 0.13877(12) 0.15100(9) -0.00516(11) 0.0245(3) Uani d . 1
C C4 0.37133(12) 0.11751(10) -0.20610(12) 0.0299(3) Uani d . 1
H H4A 0.3398 0.1219 -0.2915 0.036 Uiso calc R 1
H H4B 0.4491 0.0778 -0.1929 0.036 Uiso calc R 1
H H4C 0.3939 0.1794 -0.1743 0.036 Uiso calc R 1
C C5 -0.00048(12) 0.15053(10) 0.02358(13) 0.0323(3) Uani d . 1
H H5A -0.0502 0.2014 -0.0187 0.039 Uiso calc R 1
H H5B 0.0015 0.1585 0.1094 0.039 Uiso calc R 1
H H5C -0.0425 0.0915 -0.0014 0.039 Uiso calc R 1
C C6 0.21117(13) 0.23798(10) 0.04388(13) 0.0322(3) Uani d . 1
H H6A 0.1666 0.2927 0.0064 0.039 Uiso calc R 1
H H6B 0.3014 0.2361 0.0267 0.039 Uiso calc R 1
H H6C 0.2120 0.2410 0.1300 0.039 Uiso calc R 1
C C7 0.25868(12) 0.06192(9) 0.16572(11) 0.0238(3) Uani d . 1
C C8 0.17162(13) 0.03570(10) 0.24268(12) 0.0300(3) Uani d . 1
H H8 0.0845 0.0182 0.2114 0.036 Uiso calc R 1
C C9 0.21170(15) 0.03505(10) 0.36421(13) 0.0351(4) Uani d . 1
H H9 0.1512 0.0195 0.4163 0.042 Uiso calc R 1
C C10 0.33994(15) 0.05701(11) 0.41012(13) 0.0369(4) Uani d . 1
H H10 0.3678 0.0561 0.4935 0.044 Uiso calc R 1
C C11 0.42687(14) 0.08027(10) 0.33391(13) 0.0350(4) Uani d . 1
H H11 0.5152 0.0941 0.3653 0.042 Uiso calc R 1
C C12 0.38697(13) 0.08371(10) 0.21185(12) 0.0298(3) Uani d . 1
H H12 0.4473 0.1009 0.1603 0.036 Uiso calc R 1
C C13 0.15714(12) -0.01865(10) -0.31306(12) 0.0276(3) Uani d . 1
C C14 0.14893(14) -0.11871(10) -0.35257(13) 0.0345(3) Uani d . 1
H H14A 0.0570 -0.1405 -0.3662 0.041 Uiso calc R 1
H H14B 0.1877 -0.1273 -0.4264 0.041 Uiso calc R 1
C C15 0.22670(13) -0.16867(10) -0.25062(12) 0.0302(3) Uani d . 1
C C16 0.25781(14) -0.26120(11) -0.23552(14) 0.0397(4) Uani d . 1
H H16 0.2292 -0.3046 -0.2967 0.048 Uiso calc R 1
C C17 0.33152(15) -0.29019(11) -0.12971(15) 0.0434(4) Uani d . 1
H H17 0.3546 -0.3536 -0.1187 0.052 Uiso calc R 1
C C18 0.37126(14) -0.22708(11) -0.04071(14) 0.0372(4) Uani d . 1
H H18 0.4208 -0.2481 0.0314 0.045 Uiso calc R 1
C C19 0.34072(12) -0.13343(10) -0.05376(13) 0.0302(3) Uani d . 1
H H19 0.3680 -0.0906 0.0083 0.036 Uiso calc R 1
C C20 0.26919(11) -0.10490(9) -0.16041(11) 0.0247(3) Uani d . 1
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_publ_flag
C1 O1 N1 104.14(8) y
C7 N1 O1 107.11(9) y
C7 N1 C3 116.43(10) y
O1 N1 C3 100.97(9) y
C13 N2 C20 110.21(11) y
C13 N2 C1 119.82(11) y
C20 N2 C1 128.24(10) y
O1 C1 N2 109.60(10) ?
O1 C1 C4 106.42(10) ?
N2 C1 C4 109.32(10) ?
O1 C1 C2 104.82(10) ?
N2 C1 C2 110.52(10) ?
C4 C1 C2 115.87(11) ?
C3 C2 C1 104.80(10) ?
C3 C2 H2A 110.8 ?
C1 C2 H2A 110.8 ?
C3 C2 H2B 110.8 ?
C1 C2 H2B 110.8 ?
H2A C2 H2B 108.9 ?
N1 C3 C5 109.37(10) ?
N1 C3 C6 112.48(11) ?
C5 C3 C6 110.64(11) ?
N1 C3 C2 99.47(10) ?
C5 C3 C2 112.67(11) ?
C6 C3 C2 111.77(11) ?
C1 C4 H4A 109.5 ?
C1 C4 H4B 109.5 ?
H4A C4 H4B 109.5 ?
C1 C4 H4C 109.5 ?
H4A C4 H4C 109.5 ?
H4B C4 H4C 109.5 ?
C3 C5 H5A 109.5 ?
C3 C5 H5B 109.5 ?
H5A C5 H5B 109.5 ?
C3 C5 H5C 109.5 ?
H5A C5 H5C 109.5 ?
H5B C5 H5C 109.5 ?
C3 C6 H6A 109.5 ?
C3 C6 H6B 109.5 ?
H6A C6 H6B 109.5 ?
C3 C6 H6C 109.5 ?
H6A C6 H6C 109.5 ?
H6B C6 H6C 109.5 ?
C12 C7 C8 119.44(13) ?
C12 C7 N1 124.06(11) ?
C8 C7 N1 116.50(11) ?
C9 C8 C7 120.26(13) ?
C9 C8 H8 119.9 ?
C7 C8 H8 119.9 ?
C8 C9 C10 120.15(13) ?
C8 C9 H9 119.9 ?
C10 C9 H9 119.9 ?
C11 C10 C9 119.54(14) ?
C11 C10 H10 120.2 ?
C9 C10 H10 120.2 ?
C10 C11 C12 120.89(14) ?
C10 C11 H11 119.6 ?
C12 C11 H11 119.6 ?
C7 C12 C11 119.65(12) ?
C7 C12 H12 120.2 ?
C11 C12 H12 120.2 ?
O2 C13 N2 124.65(13) ?
O2 C13 C14 126.98(13) ?
N2 C13 C14 108.37(12) ?
C15 C14 C13 103.35(11) ?
C15 C14 H14A 111.1 ?
C13 C14 H14A 111.1 ?
C15 C14 H14B 111.1 ?
C13 C14 H14B 111.1 ?
H14A C14 H14B 109.1 ?
C16 C15 C20 120.30(14) ?
C16 C15 C14 130.75(14) ?
C20 C15 C14 108.95(13) ?
C15 C16 C17 119.15(15) ?
C15 C16 H16 120.4 ?
C17 C16 H16 120.4 ?
C18 C17 C16 120.12(15) ?
C18 C17 H17 119.9 ?
C16 C17 H17 119.9 ?
C17 C18 C19 121.76(15) ?
C17 C18 H18 119.1 ?
C19 C18 H18 119.1 ?
C20 C19 C18 117.71(14) ?
C20 C19 H19 121.1 ?
C18 C19 H19 121.1 ?
C19 C20 C15 120.94(13) ?
C19 C20 N2 130.09(12) ?
C15 C20 N2 108.95(12) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 1.4128(15) y
O1 N1 1.4730(13) y
O2 C13 1.2221(17) y
N1 C7 1.4328(17) y
N1 C3 1.5083(17) y
N2 C13 1.3834(17) y
N2 C20 1.4257(17) y
N2 C1 1.4934(18) y
C1 C4 1.5186(17) ?
C1 C2 1.5426(18) ?
C2 C3 1.5328(19) ?
C2 H2A 0.9900 ?
C2 H2B 0.9900 ?
C3 C5 1.5206(18) ?
C3 C6 1.5247(19) ?
C4 H4A 0.9800 ?
C4 H4B 0.9800 ?
C4 H4C 0.9800 ?
C5 H5A 0.9800 ?
C5 H5B 0.9800 ?
C5 H5C 0.9800 ?
C6 H6A 0.9800 ?
C6 H6B 0.9800 ?
C6 H6C 0.9800 ?
C7 C12 1.3860(19) ?
C7 C8 1.3970(18) ?
C8 C9 1.383(2) ?
C8 H8 0.9500 ?
C9 C10 1.386(2) ?
C9 H9 0.9500 ?
C10 C11 1.379(2) ?
C10 H10 0.9500 ?
C11 C12 1.390(2) ?
C11 H11 0.9500 ?
C12 H12 0.9500 ?
C13 C14 1.512(2) ?
C14 C15 1.495(2) ?
C14 H14A 0.9900 ?
C14 H14B 0.9900 ?
C15 C16 1.379(2) ?
C15 C20 1.4003(19) ?
C16 C17 1.390(2) ?
C16 H16 0.9500 ?
C17 C18 1.379(2) ?
C17 H17 0.9500 ?
C18 C19 1.392(2) ?
C18 H18 0.9500 ?
C19 C20 1.3860(19) ?
C19 H19 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
C1 O1 N1 C7 -173.08(10)
C1 O1 N1 C3 -50.81(11)
N1 O1 C1 N2 -85.70(10)
N1 O1 C1 C4 156.20(10)
N1 O1 C1 C2 32.93(12)
C13 N2 C1 O1 175.20(9)
C20 N2 C1 O1 -21.35(15)
C13 N2 C1 C4 -68.51(14)
C20 N2 C1 C4 94.93(14)
C13 N2 C1 C2 60.16(14)
C20 N2 C1 C2 -136.39(12)
O1 C1 C2 C3 -3.43(13)
N2 C1 C2 C3 114.58(11)
C4 C1 C2 C3 -120.39(12)
C7 N1 C3 C5 -80.50(13)
O1 N1 C3 C5 163.97(10)
C7 N1 C3 C6 42.86(14)
O1 N1 C3 C6 -72.67(12)
C7 N1 C3 C2 161.28(10)
O1 N1 C3 C2 45.75(10)
C1 C2 C3 N1 -26.08(12)
C1 C2 C3 C5 -141.81(12)
C1 C2 C3 C6 92.87(13)
O1 N1 C7 C12 16.82(16)
C3 N1 C7 C12 -95.22(15)
O1 N1 C7 C8 -162.54(11)
C3 N1 C7 C8 85.42(14)
C12 C7 C8 C9 2.6(2)
N1 C7 C8 C9 -178.05(12)
C7 C8 C9 C10 -2.5(2)
C8 C9 C10 C11 0.6(2)
C9 C10 C11 C12 1.3(2)
C8 C7 C12 C11 -0.8(2)
N1 C7 C12 C11 179.90(13)
C10 C11 C12 C7 -1.1(2)
C20 N2 C13 O2 -175.45(12)
C1 N2 C13 O2 -9.25(18)
C20 N2 C13 C14 4.16(13)
C1 N2 C13 C14 170.37(10)
O2 C13 C14 C15 175.51(12)
N2 C13 C14 C15 -4.10(14)
C13 C14 C15 C16 -177.97(14)
C13 C14 C15 C20 2.61(14)
C20 C15 C16 C17 0.1(2)
C14 C15 C16 C17 -179.23(14)
C15 C16 C17 C18 0.8(2)
C16 C17 C18 C19 -0.7(2)
C17 C18 C19 C20 -0.5(2)
C18 C19 C20 C15 1.46(18)
C18 C19 C20 N2 179.55(12)
C16 C15 C20 C19 -1.31(19)
C14 C15 C20 C19 178.18(11)
C16 C15 C20 N2 -179.76(11)
C14 C15 C20 N2 -0.27(14)
C13 N2 C20 C19 179.24(12)
C1 N2 C20 C19 14.5(2)
C13 N2 C20 C15 -2.49(13)
C1 N2 C20 C15 -167.22(11)
