#------------------------------------------------------------------------------
#$Date: 2025-08-22 00:26:11 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301853 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/61/7106125.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_7106125
loop_
_publ_author_name
'Santosh J. Gharpure'
'A. M. Sathiyanarayanan'
_publ_section_title
;
 Stereoselective synthesis of oxazino [4,3-a]indoles employing
 oxa-Pictet-Spengler reaction of indoles bearing N-tethered vinylogous
 caronate
;
_journal_name_full               Chem.Commun.
_journal_page_first              3625
_journal_paper_doi               10.1039/c0cc05558a
_journal_volume                  47
_journal_year                    2011
_chemical_formula_sum            'C14 H15 N O3'
_chemical_formula_weight         245.27
_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                 100.186(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.05110(10)
_cell_length_b                   14.5244(5)
_cell_length_c                   14.0584(5)
_cell_measurement_reflns_used    2420
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.29
_cell_measurement_theta_min      2.80
_cell_volume                     1216.10(6)
_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 0.965
_diffrn_measured_fraction_theta_max 0.932
_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  0.0323
_diffrn_reflns_av_sigmaI/netI    0.0418
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8987
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         3.17
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.9860
_exptl_absorpt_correction_T_min  0.9677
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            clear
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.901
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2805
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.901
_refine_ls_R_factor_all          0.0749
_refine_ls_R_factor_gt           0.0440
_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1207
_refine_ls_wR_factor_ref         0.1434
_reflns_number_gt                1883
_reflns_number_total             2805
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0cc05558a.txt
_cod_data_source_block           pox
_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               7106125
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 0.6820(2) 0.21807(10) 0.82592(11) 0.0290(4) Uani 1 1 d . . .
C2 C 0.5965(3) 0.19786(12) 0.90905(12) 0.0371(4) Uani 1 1 d . . .
H2 H 0.6072 0.2399 0.9596 0.044 Uiso 1 1 calc R . .
C3 C 0.4953(3) 0.11350(13) 0.91394(14) 0.0453(5) Uani 1 1 d . . .
H3 H 0.4368 0.0991 0.9690 0.054 Uiso 1 1 calc R . .
C4 C 0.4769(3) 0.04862(12) 0.83963(15) 0.0487(5) Uani 1 1 d . . .
H4 H 0.4024 -0.0067 0.8445 0.058 Uiso 1 1 calc R . .
C5 C 0.5693(3) 0.06699(12) 0.75950(14) 0.0424(4) Uani 1 1 d . . .
H5 H 0.5614 0.0239 0.7101 0.051 Uiso 1 1 calc R . .
C6 C 0.6752(2) 0.15129(10) 0.75331(11) 0.0313(4) Uani 1 1 d . . .
C7 C 0.7913(2) 0.18869(11) 0.68079(11) 0.0320(4) Uani 1 1 d . . .
C8 C 0.8829(2) 0.28388(10) 0.71811(11) 0.0295(4) Uani 1 1 d . . .
C9 C 1.0243(3) 0.38056(14) 0.61000(14) 0.0485(5) Uani 1 1 d . . .
H9A H 1.0689 0.4423 0.6316 0.058 Uiso 1 1 calc R . .
H9B H 0.9959 0.3796 0.5399 0.058 Uiso 1 1 calc R . .
C10 C 1.2055(3) 0.31200(13) 0.64948(13) 0.0417(4) Uani 1 1 d . . .
H10A H 1.2042 0.2596 0.6065 0.050 Uiso 1 1 calc R . .
H10B H 1.3530 0.3403 0.6594 0.050 Uiso 1 1 calc R . .
C11 C 1.1414(2) 0.28391(11) 0.74418(11) 0.0321(4) Uani 1 1 d . . .
H11 H 1.2005 0.2230 0.7651 0.039 Uiso 1 1 calc R . .
C12 C 1.1255(2) 0.34832(11) 0.89942(11) 0.0330(4) Uani 1 1 d . . .
H12 H 1.1484 0.2864 0.9271 0.040 Uiso 1 1 calc R . .
C13 C 0.8773(3) 0.36691(11) 0.87187(12) 0.0348(4) Uani 1 1 d . . .
H13A H 0.8078 0.3633 0.9289 0.042 Uiso 1 1 calc R . .
H13B H 0.8537 0.4285 0.8453 0.042 Uiso 1 1 calc R . .
C14 C 1.2461(3) 0.41746(12) 0.97019(13) 0.0443(4) Uani 1 1 d . . .
H14A H 1.4038 0.4038 0.9828 0.067 Uiso 1 1 calc R . .
H14B H 1.1883 0.4144 1.0294 0.067 Uiso 1 1 calc R . .
H14C H 1.2231 0.4782 0.9434 0.067 Uiso 1 1 calc R . .
N1 N 0.77355(19) 0.29991(8) 0.80060(9) 0.0307(3) Uani 1 1 d . . .
O1 O 0.8193(2) 0.15665(9) 0.60372(9) 0.0493(4) Uani 1 1 d . . .
O2 O 0.82686(17) 0.35275(7) 0.64663(8) 0.0388(3) Uani 1 1 d . . .
O3 O 1.22115(16) 0.35309(7) 0.81323(8) 0.0348(3) 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 128.50(14) . . ?
N1 C1 C6 111.61(14) . . ?
C2 C1 C6 119.86(14) . . ?
C3 C2 C1 117.69(16) . . ?
C3 C2 H2 121.2 . . ?
C1 C2 H2 121.2 . . ?
C2 C3 C4 122.71(17) . . ?
C2 C3 H3 118.6 . . ?
C4 C3 H3 118.6 . . ?
C5 C4 C3 119.59(16) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 118.83(16) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C5 C6 C1 121.15(15) . . ?
C5 C6 C7 131.49(15) . . ?
C1 C6 C7 107.36(13) . . ?
O1 C7 C6 130.27(15) . . ?
O1 C7 C8 123.06(15) . . ?
C6 C7 C8 106.66(13) . . ?
O2 C8 N1 111.59(12) . . ?
O2 C8 C11 105.89(12) . . ?
N1 C8 C11 113.36(12) . . ?
O2 C8 C7 111.37(12) . . ?
N1 C8 C7 103.18(12) . . ?
C11 C8 C7 111.61(12) . . ?
O2 C9 C10 106.12(14) . . ?
O2 C9 H9A 110.5 . . ?
C10 C9 H9A 110.5 . . ?
O2 C9 H9B 110.5 . . ?
C10 C9 H9B 110.5 . . ?
H9A C9 H9B 108.7 . . ?
C11 C10 C9 102.66(13) . . ?
C11 C10 H10A 111.2 . . ?
C9 C10 H10A 111.2 . . ?
C11 C10 H10B 111.2 . . ?
C9 C10 H10B 111.2 . . ?
H10A C10 H10B 109.1 . . ?
O3 C11 C10 107.62(13) . . ?
O3 C11 C8 111.71(12) . . ?
C10 C11 C8 101.47(12) . . ?
O3 C11 H11 111.8 . . ?
C10 C11 H11 111.8 . . ?
C8 C11 H11 111.8 . . ?
O3 C12 C13 107.88(13) . . ?
O3 C12 C14 107.74(12) . . ?
C13 C12 C14 113.22(13) . . ?
O3 C12 H12 109.3 . . ?
C13 C12 H12 109.3 . . ?
C14 C12 H12 109.3 . . ?
N1 C13 C12 110.21(12) . . ?
N1 C13 H13A 109.6 . . ?
C12 C13 H13A 109.6 . . ?
N1 C13 H13B 109.6 . . ?
C12 C13 H13B 109.6 . . ?
H13A C13 H13B 108.1 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C1 N1 C8 109.09(12) . . ?
C1 N1 C13 122.69(13) . . ?
C8 N1 C13 117.05(12) . . ?
C8 O2 C9 110.03(12) . . ?
C11 O3 C12 113.84(11) . . ?
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 1.384(2) . ?
C1 C2 1.391(2) . ?
C1 C6 1.403(2) . ?
C2 C3 1.377(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.397(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.369(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.392(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.443(2) . ?
C7 O1 1.2182(19) . ?
C7 C8 1.546(2) . ?
C8 O2 1.4159(18) . ?
C8 N1 1.452(2) . ?
C8 C11 1.543(2) . ?
C9 O2 1.440(2) . ?
C9 C10 1.512(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.507(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 O3 1.4209(18) . ?
C11 H11 0.9800 . ?
C12 O3 1.4340(19) . ?
C12 C13 1.508(2) . ?
C12 C14 1.508(2) . ?
C12 H12 0.9800 . ?
C13 N1 1.4567(19) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
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
N1 C1 C2 C3 174.22(14) . . . . ?
C6 C1 C2 C3 -3.7(2) . . . . ?
C1 C2 C3 C4 0.2(2) . . . . ?
C2 C3 C4 C5 2.4(3) . . . . ?
C3 C4 C5 C6 -1.5(3) . . . . ?
C4 C5 C6 C1 -2.0(2) . . . . ?
C4 C5 C6 C7 177.99(16) . . . . ?
N1 C1 C6 C5 -173.54(14) . . . . ?
C2 C1 C6 C5 4.7(2) . . . . ?
N1 C1 C6 C7 6.44(16) . . . . ?
C2 C1 C6 C7 -175.30(13) . . . . ?
C5 C6 C7 O1 3.1(3) . . . . ?
C1 C6 C7 O1 -176.89(16) . . . . ?
C5 C6 C7 C8 -177.07(16) . . . . ?
C1 C6 C7 C8 2.96(15) . . . . ?
O1 C7 C8 O2 49.51(19) . . . . ?
C6 C7 C8 O2 -130.35(13) . . . . ?
O1 C7 C8 N1 169.34(14) . . . . ?
C6 C7 C8 N1 -10.52(14) . . . . ?
O1 C7 C8 C11 -68.60(19) . . . . ?
C6 C7 C8 C11 111.54(14) . . . . ?
O2 C9 C10 C11 -29.95(18) . . . . ?
C9 C10 C11 O3 -81.05(15) . . . . ?
C9 C10 C11 C8 36.37(16) . . . . ?
O2 C8 C11 O3 83.17(15) . . . . ?
N1 C8 C11 O3 -39.49(17) . . . . ?
C7 C8 C11 O3 -155.48(13) . . . . ?
O2 C8 C11 C10 -31.24(15) . . . . ?
N1 C8 C11 C10 -153.90(13) . . . . ?
C7 C8 C11 C10 90.11(15) . . . . ?
O3 C12 C13 N1 58.57(16) . . . . ?
C14 C12 C13 N1 177.70(14) . . . . ?
C2 C1 N1 C8 168.12(14) . . . . ?
C6 C1 N1 C8 -13.80(16) . . . . ?
C2 C1 N1 C13 25.6(2) . . . . ?
C6 C1 N1 C13 -156.36(13) . . . . ?
O2 C8 N1 C1 134.18(12) . . . . ?
C11 C8 N1 C1 -106.37(14) . . . . ?
C7 C8 N1 C1 14.50(15) . . . . ?
O2 C8 N1 C13 -80.89(15) . . . . ?
C11 C8 N1 C13 38.57(17) . . . . ?
C7 C8 N1 C13 159.44(12) . . . . ?
C12 C13 N1 C1 91.39(17) . . . . ?
C12 C13 N1 C8 -48.43(17) . . . . ?
N1 C8 O2 C9 136.98(14) . . . . ?
C11 C8 O2 C9 13.20(16) . . . . ?
C7 C8 O2 C9 -108.30(14) . . . . ?
C10 C9 O2 C8 10.40(19) . . . . ?
C10 C11 O3 C12 165.10(12) . . . . ?
C8 C11 O3 C12 54.55(16) . . . . ?
C13 C12 O3 C11 -64.46(15) . . . . ?
C14 C12 O3 C11 172.98(12) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139181773
