#------------------------------------------------------------------------------
#$Date: 2022-04-22 18:35:43 +0300 (Fri, 22 Apr 2022) $
#$Revision: 274634 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/42/7204299.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_7204299
loop_
_publ_author_name
'Zhang, Yan'
'Xue, Jie'
'Gao, Yi'
'Fun, Hoong-Kun'
'Xu, Jian-Hua'
_publ_section_title
;
 Photoinduced [2+2] cycloadditions (the Paterno--Büchi reaction) of
 1-acetylisatin with enol ethers---regioselectivity, diastereoselectivity
 and acid catalysed transformations of the spirooxetane products
;
_journal_coden_ASTM              JCSPCE
_journal_issue                   3
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              345
_journal_page_last               353
_journal_paper_doi               10.1039/b109697d
_journal_year                    2002
_chemical_formula_sum            'C14 H11 N O4'
_chemical_formula_weight         257.24
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 121.111(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   19.2158(1)
_cell_length_b                   9.2422(2)
_cell_length_c                   15.6965(3)
_cell_measurement_reflns_used    3352
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.29
_cell_measurement_theta_min      2.48
_cell_volume                     2386.69(7)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material
;
SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990)
;
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type
;
Siemens SMART CCD area detector diffractometer
;
_diffrn_measurement_method       'ω 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  0.1385
_diffrn_reflns_av_sigmaI/netI    0.1312
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8222
_diffrn_reflns_theta_full        28.30
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         2.48
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.532
_refine_diff_density_min         -0.476
_refine_diff_density_rms         0.116
_refine_ls_extinction_coef       0.0128(19)
_refine_ls_extinction_expression Fc^*^==kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.886
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2893
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.886
_refine_ls_R_factor_all          0.1383
_refine_ls_R_factor_gt           0.0789
_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)+(0.1078P)²+0.0000P] where P==(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1902
_refine_ls_wR_factor_ref         0.2124
_reflns_number_gt                1349
_reflns_number_total             2893
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            b109697d.txt
_cod_data_source_block           compound8
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7204299
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
O1 O 0.22503(16) 0.3396(3) 0.38753(17) 0.0738(8) Uani 1 1 d . . .
O2 O 0.22868(11) 0.1421(2) 0.29500(13) 0.0520(6) Uani 1 1 d . . .
O3 O 0.11606(17) -0.1083(3) 0.23077(17) 0.0834(9) Uani 1 1 d . . .
O4 O 0.05513(16) -0.1797(3) -0.06136(19) 0.0741(8) Uani 1 1 d . . .
N1 N 0.10048(13) -0.0461(2) 0.07802(16) 0.0397(6) Uani 1 1 d . . .
C1 C 0.11670(15) 0.0826(3) 0.04060(19) 0.0361(6) Uani 1 1 d . . .
C2 C 0.1068(2) 0.1084(3) -0.0517(2) 0.0550(9) Uani 1 1 d . . .
H2A H 0.0858 0.0376 -0.1009 0.066 Uiso 1 1 calc R . .
C3 C 0.1291(2) 0.2423(4) -0.0686(3) 0.0709(11) Uani 1 1 d . . .
H3A H 0.1236 0.2612 -0.1301 0.085 Uiso 1 1 calc R . .
C4 C 0.1594(3) 0.3484(4) 0.0031(3) 0.0728(11) Uani 1 1 d . . .
H4A H 0.1730 0.4383 -0.0108 0.087 Uiso 1 1 calc R . .
C5 C 0.16964(19) 0.3223(3) 0.0957(2) 0.0507(8) Uani 1 1 d . . .
H5A H 0.1922 0.3924 0.1453 0.061 Uiso 1 1 calc R . .
C6 C 0.14588(15) 0.1907(3) 0.11300(18) 0.0354(6) Uani 1 1 d . . .
C7 C 0.14957(16) 0.1345(3) 0.20401(18) 0.0374(6) Uani 1 1 d . . .
C9 C 0.1689(2) 0.4335(4) 0.3175(3) 0.0725(11) Uani 1 1 d . . .
H9A H 0.1770 0.5331 0.3221 0.087 Uiso 1 1 calc R . .
C10 C 0.1035(2) 0.3735(4) 0.2440(2) 0.0609(9) Uani 1 1 d . . .
H10A H 0.0597 0.4224 0.1923 0.073 Uiso 1 1 calc R . .
C11 C 0.11135(17) 0.2145(3) 0.2575(2) 0.0451(7) Uani 1 1 d . . .
H11A H 0.0666 0.1647 0.2582 0.054 Uiso 1 1 calc R . .
C8 C 0.19467(19) 0.1990(4) 0.3502(2) 0.0547(9) Uani 1 1 d . . .
H8A H 0.1965 0.1322 0.3998 0.066 Uiso 1 1 calc R . .
C12 C 0.12071(17) -0.0220(3) 0.1766(2) 0.0484(8) Uani 1 1 d . . .
C13 C 0.07453(17) -0.1778(3) 0.0249(2) 0.0480(8) Uani 1 1 d . . .
C14 C 0.0698(2) -0.3078(3) 0.0780(3) 0.0708(11) Uani 1 1 d . . .
H14A H 0.0880 -0.2830 0.1458 0.106 Uiso 1 1 calc R . .
H14B H 0.1038 -0.3830 0.0768 0.106 Uiso 1 1 calc R . .
H14C H 0.0146 -0.3413 0.0457 0.106 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
C9 O1 C8 105.2(3) . . ?
C8 O2 C7 92.29(19) . . ?
C12 N1 C13 126.8(2) . . ?
C12 N1 C1 109.0(2) . . ?
C13 N1 C1 124.0(2) . . ?
C2 C1 C6 120.7(2) . . ?
C2 C1 N1 129.3(2) . . ?
C6 C1 N1 110.0(2) . . ?
C3 C2 C1 118.0(3) . . ?
C3 C2 H2A 121.0 . . ?
C1 C2 H2A 121.0 . . ?
C4 C3 C2 121.6(3) . . ?
C4 C3 H3A 119.2 . . ?
C2 C3 H3A 119.2 . . ?
C3 C4 C5 120.4(3) . . ?
C3 C4 H4A 119.8 . . ?
C5 C4 H4A 119.8 . . ?
C6 C5 C4 118.7(3) . . ?
C6 C5 H5A 120.7 . . ?
C4 C5 H5A 120.7 . . ?
C5 C6 C1 120.5(2) . . ?
C5 C6 C7 130.0(2) . . ?
C1 C6 C7 109.4(2) . . ?
O2 C7 C6 115.7(2) . . ?
O2 C7 C12 111.5(2) . . ?
C6 C7 C12 103.3(2) . . ?
O2 C7 C11 89.55(19) . . ?
C6 C7 C11 123.4(2) . . ?
C12 C7 C11 113.4(2) . . ?
C10 C9 O1 115.8(3) . . ?
C10 C9 H9A 122.1 . . ?
O1 C9 H9A 122.1 . . ?
C9 C10 C11 108.2(3) . . ?
C9 C10 H10A 125.9 . . ?
C11 C10 H10A 125.9 . . ?
C10 C11 C8 102.1(2) . . ?
C10 C11 C7 115.8(2) . . ?
C8 C11 C7 85.1(2) . . ?
C10 C11 H11A 116.3 . . ?
C8 C11 H11A 116.3 . . ?
C7 C11 H11A 116.3 . . ?
O1 C8 O2 111.6(3) . . ?
O1 C8 C11 108.3(3) . . ?
O2 C8 C11 92.3(2) . . ?
O1 C8 H8A 114.2 . . ?
O2 C8 H8A 114.2 . . ?
C11 C8 H8A 114.2 . . ?
O3 C12 N1 126.5(3) . . ?
O3 C12 C7 125.3(3) . . ?
N1 C12 C7 108.3(2) . . ?
O4 C13 N1 119.1(3) . . ?
O4 C13 C14 122.9(3) . . ?
N1 C13 C14 118.0(3) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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 1.378(4) . ?
O1 C8 1.421(4) . ?
O2 C8 1.428(3) . ?
O2 C7 1.453(3) . ?
O3 C12 1.202(3) . ?
O4 C13 1.205(4) . ?
N1 C12 1.405(4) . ?
N1 C13 1.412(3) . ?
N1 C1 1.430(3) . ?
C1 C2 1.381(4) . ?
C1 C6 1.395(4) . ?
C2 C3 1.379(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.375(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.384(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.375(4) . ?
C5 H5A 0.9300 . ?
C6 C7 1.487(3) . ?
C7 C12 1.529(4) . ?
C7 C11 1.559(4) . ?
C9 C10 1.312(5) . ?
C9 H9A 0.9300 . ?
C10 C11 1.481(4) . ?
C10 H10A 0.9300 . ?
C11 C8 1.514(4) . ?
C11 H11A 0.9800 . ?
C8 H8A 0.9800 . ?
C13 C14 1.492(4) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
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
C12 N1 C1 C2 179.4(3) . . . . ?
C13 N1 C1 C2 4.0(4) . . . . ?
C12 N1 C1 C6 -1.0(3) . . . . ?
C13 N1 C1 C6 -176.4(2) . . . . ?
C6 C1 C2 C3 2.0(5) . . . . ?
N1 C1 C2 C3 -178.4(3) . . . . ?
C1 C2 C3 C4 -0.8(6) . . . . ?
C2 C3 C4 C5 1.1(6) . . . . ?
C3 C4 C5 C6 -2.7(6) . . . . ?
C4 C5 C6 C1 3.9(5) . . . . ?
C4 C5 C6 C7 -179.8(3) . . . . ?
C2 C1 C6 C5 -3.7(4) . . . . ?
N1 C1 C6 C5 176.7(2) . . . . ?
C2 C1 C6 C7 179.4(2) . . . . ?
N1 C1 C6 C7 -0.3(3) . . . . ?
C8 O2 C7 C6 134.2(2) . . . . ?
C8 O2 C7 C12 -108.2(2) . . . . ?
C8 O2 C7 C11 6.8(2) . . . . ?
C5 C6 C7 O2 -53.2(4) . . . . ?
C1 C6 C7 O2 123.4(2) . . . . ?
C5 C6 C7 C12 -175.3(3) . . . . ?
C1 C6 C7 C12 1.3(3) . . . . ?
C5 C6 C7 C11 54.6(4) . . . . ?
C1 C6 C7 C11 -128.8(3) . . . . ?
C8 O1 C9 C10 5.0(4) . . . . ?
O1 C9 C10 C11 -1.9(4) . . . . ?
C9 C10 C11 C8 -1.9(3) . . . . ?
C9 C10 C11 C7 -92.3(3) . . . . ?
O2 C7 C11 C10 94.7(3) . . . . ?
C6 C7 C11 C10 -26.3(4) . . . . ?
C12 C7 C11 C10 -152.1(3) . . . . ?
O2 C7 C11 C8 -6.4(2) . . . . ?
C6 C7 C11 C8 -127.4(3) . . . . ?
C12 C7 C11 C8 106.8(2) . . . . ?
C9 O1 C8 O2 94.3(3) . . . . ?
C9 O1 C8 C11 -5.9(3) . . . . ?
C7 O2 C8 O1 -117.8(3) . . . . ?
C7 O2 C8 C11 -7.0(2) . . . . ?
C10 C11 C8 O1 4.9(3) . . . . ?
C7 C11 C8 O1 120.2(2) . . . . ?
C10 C11 C8 O2 -108.8(2) . . . . ?
C7 C11 C8 O2 6.6(2) . . . . ?
C13 N1 C12 O3 -3.3(5) . . . . ?
C1 N1 C12 O3 -178.5(3) . . . . ?
C13 N1 C12 C7 177.0(2) . . . . ?
C1 N1 C12 C7 1.8(3) . . . . ?
O2 C7 C12 O3 53.5(4) . . . . ?
C6 C7 C12 O3 178.4(3) . . . . ?
C11 C7 C12 O3 -45.7(4) . . . . ?
O2 C7 C12 N1 -126.8(2) . . . . ?
C6 C7 C12 N1 -1.9(3) . . . . ?
C11 C7 C12 N1 134.0(2) . . . . ?
C12 N1 C13 O4 176.1(3) . . . . ?
C1 N1 C13 O4 -9.4(4) . . . . ?
C12 N1 C13 C14 -1.9(4) . . . . ?
C1 N1 C13 C14 172.6(3) . . . . ?
loop_
_cod_changelog_entry_id
_cod_changelog_entry_author
_cod_changelog_entry_date
_cod_changelog_entry_text
1 'Vaitkus, Antanas' 2022-04-22T18:30:00+03:00
'Updated bibliographic information.'
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4416417
