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#$Date: 2025-08-22 00:26:11 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301853 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/59/7105925.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_7105925
loop_
_publ_author_name
'Jing An '
'Ning-Jie Chang'
'Li-Dong Song'
'Yu-Qin Jin'
'Ying Ma'
'Jia-Rong Chen '
' Wen-Jing Xiao'
_publ_section_title
;
 An Efficient and General Synthesis of Oxazino[4,3-a]indoles by A Cascade
 Addition-Cyclization Reaction of (1H-Indol-2-yl)methanols and Vinyl
 Sulfonium Salts
;
_journal_name_full               Chem.Commun.
_journal_page_first              1869
_journal_paper_doi               10.1039/c0cc03823g
_journal_volume                  47
_journal_year                    2011
_chemical_formula_moiety         'C12 H12 N2 O'
_chemical_formula_sum            'C12 H12 N2 O'
_chemical_formula_weight         200.24
_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                 98.375(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.5035(12)
_cell_length_b                   8.0361(9)
_cell_length_c                   12.2743(14)
_cell_measurement_reflns_used    3329
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.86
_cell_measurement_theta_min      3.04
_cell_volume                     1025.0(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0307
_diffrn_reflns_av_sigmaI/netI    0.0239
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12261
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         1.96
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2541
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0489
_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)+(0.0821P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1371
_refine_ls_wR_factor_ref         0.1458
_reflns_number_gt                1780
_reflns_number_total             2541
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            C0CC03823G.TXT
_cod_data_source_block           101104cm
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7105925
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
C1 C 0.16565(13) 0.13074(17) 0.19738(11) 0.0515(4) Uani 1 1 d . . .
C2 C 0.24280(16) 0.0599(2) 0.28771(13) 0.0670(4) Uani 1 1 d . . .
H2 H 0.2102 -0.0170 0.3331 0.080 Uiso 1 1 calc R . .
C3 C 0.37007(18) 0.1096(3) 0.30643(18) 0.0891(6) Uani 1 1 d . . .
H3 H 0.4243 0.0658 0.3662 0.107 Uiso 1 1 calc R . .
C4 C 0.41932(19) 0.2246(3) 0.2375(2) 0.0960(7) Uani 1 1 d . . .
H4 H 0.5055 0.2553 0.2525 0.115 Uiso 1 1 calc R . .
C5 C 0.34380(18) 0.2920(2) 0.14953(17) 0.0850(6) Uani 1 1 d . . .
H5 H 0.3780 0.3678 0.1044 0.102 Uiso 1 1 calc R . .
C6 C 0.21429(15) 0.24668(19) 0.12714(12) 0.0596(4) Uani 1 1 d . . .
C7 C 0.11106(16) 0.29173(18) 0.04598(12) 0.0603(4) Uani 1 1 d . . .
H7 H 0.1144 0.3661 -0.0116 0.072 Uiso 1 1 calc R . .
C8 C 0.00541(14) 0.20640(14) 0.06732(10) 0.0476(3) Uani 1 1 d . . .
C9 C -0.12593(15) 0.20632(16) 0.00743(11) 0.0527(4) Uani 1 1 d . . .
C10 C -0.18620(14) 0.0630(2) 0.16895(12) 0.0625(4) Uani 1 1 d . . .
H10A H -0.2474 -0.0235 0.1802 0.075 Uiso 1 1 calc R . .
H10B H -0.1982 0.1543 0.2181 0.075 Uiso 1 1 calc R . .
C11 C -0.05322(13) -0.00387(17) 0.19816(11) 0.0533(4) Uani 1 1 d . . .
H11A H -0.0333 -0.0173 0.2774 0.064 Uiso 1 1 calc R . .
H11B H -0.0470 -0.1120 0.1642 0.064 Uiso 1 1 calc R . .
C12 C -0.34675(17) 0.1207(3) 0.00354(16) 0.0897(6) Uani 1 1 d . . .
H12A H -0.3945 0.2014 0.0387 0.134 Uiso 1 1 calc R . .
H12B H -0.3829 0.0122 0.0108 0.134 Uiso 1 1 calc R . .
H12C H -0.3511 0.1477 -0.0731 0.134 Uiso 1 1 calc R . .
N1 N 0.03789(10) 0.11018(12) 0.15995(8) 0.0449(3) Uani 1 1 d . . .
N2 N -0.21352(11) 0.12156(15) 0.05536(9) 0.0576(3) Uani 1 1 d . . .
O1 O -0.15158(12) 0.27745(14) -0.08203(9) 0.0782(4) Uani 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
N1 C1 C2 130.33(14) . . ?
N1 C1 C6 107.43(13) . . ?
C2 C1 C6 122.24(14) . . ?
C3 C2 C1 116.72(18) . . ?
C3 C2 H2 121.6 . . ?
C1 C2 H2 121.6 . . ?
C2 C3 C4 121.57(19) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C5 C4 C3 121.29(18) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C6 119.50(19) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C5 C6 C7 134.39(17) . . ?
C5 C6 C1 118.67(17) . . ?
C7 C6 C1 106.93(13) . . ?
C8 C7 C6 107.42(13) . . ?
C8 C7 H7 126.3 . . ?
C6 C7 H7 126.3 . . ?
C7 C8 N1 109.32(13) . . ?
C7 C8 C9 129.61(12) . . ?
N1 C8 C9 121.07(11) . . ?
O1 C9 N2 123.30(15) . . ?
O1 C9 C8 120.95(14) . . ?
N2 C9 C8 115.73(12) . . ?
N2 C10 C11 113.13(12) . . ?
N2 C10 H10A 109.0 . . ?
C11 C10 H10A 109.0 . . ?
N2 C10 H10B 109.0 . . ?
C11 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
N1 C11 C10 109.49(11) . . ?
N1 C11 H11A 109.8 . . ?
C10 C11 H11A 109.8 . . ?
N1 C11 H11B 109.8 . . ?
C10 C11 H11B 109.8 . . ?
H11A C11 H11B 108.2 . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C1 N1 C8 108.88(11) . . ?
C1 N1 C11 129.08(11) . . ?
C8 N1 C11 121.74(11) . . ?
C9 N2 C12 119.20(14) . . ?
C9 N2 C10 121.90(12) . . ?
C12 N2 C10 117.39(13) . . ?
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 N1 1.3637(17) . ?
C1 C2 1.396(2) . ?
C1 C6 1.414(2) . ?
C2 C3 1.382(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.401(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.356(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.396(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.409(2) . ?
C7 C8 1.3620(19) . ?
C7 H7 0.9300 . ?
C8 N1 1.3762(16) . ?
C8 C9 1.466(2) . ?
C9 O1 1.2325(17) . ?
C9 N2 1.3470(18) . ?
C10 N2 1.4600(18) . ?
C10 C11 1.491(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 N1 1.4514(16) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 N2 1.450(2) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 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
N1 C1 C2 C3 -178.18(13) . . . . ?
C6 C1 C2 C3 0.6(2) . . . . ?
C1 C2 C3 C4 -0.5(2) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C3 C4 C5 C6 0.2(3) . . . . ?
C4 C5 C6 C7 179.34(16) . . . . ?
C4 C5 C6 C1 -0.1(2) . . . . ?
N1 C1 C6 C5 178.71(12) . . . . ?
C2 C1 C6 C5 -0.3(2) . . . . ?
N1 C1 C6 C7 -0.89(15) . . . . ?
C2 C1 C6 C7 -179.91(13) . . . . ?
C5 C6 C7 C8 -179.36(16) . . . . ?
C1 C6 C7 C8 0.15(15) . . . . ?
C6 C7 C8 N1 0.65(15) . . . . ?
C6 C7 C8 C9 -179.15(12) . . . . ?
C7 C8 C9 O1 8.0(2) . . . . ?
N1 C8 C9 O1 -171.75(12) . . . . ?
C7 C8 C9 N2 -173.35(13) . . . . ?
N1 C8 C9 N2 6.88(17) . . . . ?
N2 C10 C11 N1 46.54(17) . . . . ?
C2 C1 N1 C8 -179.79(13) . . . . ?
C6 C1 N1 C8 1.29(14) . . . . ?
C2 C1 N1 C11 -6.1(2) . . . . ?
C6 C1 N1 C11 175.00(12) . . . . ?
C7 C8 N1 C1 -1.23(14) . . . . ?
C9 C8 N1 C1 178.58(10) . . . . ?
C7 C8 N1 C11 -175.49(11) . . . . ?
C9 C8 N1 C11 4.33(18) . . . . ?
C10 C11 N1 C1 156.04(12) . . . . ?
C10 C11 N1 C8 -30.97(16) . . . . ?
O1 C9 N2 C12 -3.8(2) . . . . ?
C8 C9 N2 C12 177.66(13) . . . . ?
O1 C9 N2 C10 -169.37(14) . . . . ?
C8 C9 N2 C10 12.04(19) . . . . ?
C11 C10 N2 C9 -40.2(2) . . . . ?
C11 C10 N2 C12 153.92(15) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653246
2 PubChem 57873494
