#------------------------------------------------------------------------------
#$Date: 2025-08-22 00:26:11 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301853 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/61/7106124.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_7106124
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_moiety         'C16 H19 N O3'
_chemical_formula_sum            'C16 H19 N O3'
_chemical_formula_weight         273.32
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 102.944(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.4764(4)
_cell_length_b                   8.4739(3)
_cell_length_c                   17.5527(8)
_cell_measurement_temperature    298(2)
_cell_volume                     1518.66(11)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.922
_diffrn_measurement_device_type  'Bruker APEX II 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  0.0268
_diffrn_reflns_av_sigmaI/netI    0.0336
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12548
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.06
_diffrn_reflns_theta_min         2.54
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.9837
_exptl_absorpt_correction_T_min  0.9694
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker,2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.008(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3748
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.1076
_refine_ls_R_factor_gt           0.0562
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0944P)²+0.1235P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1533
_refine_ls_wR_factor_ref         0.1851
_reflns_number_gt                2032
_reflns_number_total             3748
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0cc05558a.txt
_cod_data_source_block           shelxl
_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_Hall     '-P 2yn '
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7106124
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
C1 C 0.67414(19) 0.1478(2) -0.02963(12) 0.0555(5) Uani 1 1 d . . .
C2 C 0.6333(2) 0.2212(3) -0.10170(13) 0.0732(6) Uani 1 1 d . . .
H2 H 0.5632 0.2912 -0.1114 0.088 Uiso 1 1 calc R . .
C3 C 0.7008(3) 0.1862(4) -0.15798(16) 0.0925(8) Uani 1 1 d . . .
H3 H 0.6763 0.2339 -0.2068 0.111 Uiso 1 1 calc R . .
C4 C 0.8054(3) 0.0805(4) -0.14360(16) 0.0973(9) Uani 1 1 d . . .
H4 H 0.8484 0.0582 -0.1833 0.117 Uiso 1 1 calc R . .
C5 C 0.8462(2) 0.0091(3) -0.07264(15) 0.0787(7) Uani 1 1 d . . .
H5 H 0.9165 -0.0607 -0.0638 0.094 Uiso 1 1 calc R . .
C6 C 0.78023(18) 0.0426(2) -0.01345(12) 0.0589(5) Uani 1 1 d . . .
C7 C 0.79236(18) -0.0081(2) 0.06524(13) 0.0580(5) Uani 1 1 d . . .
C8 C 0.69699(15) 0.0643(2) 0.09324(11) 0.0485(4) Uani 1 1 d . . .
C9 C 0.65956(16) 0.0571(2) 0.17038(11) 0.0496(5) Uani 1 1 d . . .
H9 H 0.6040 -0.0357 0.1713 0.059 Uiso 1 1 calc R . .
C10 C 0.47551(16) 0.2142(2) 0.12000(12) 0.0558(5) Uani 1 1 d . . .
H10 H 0.4287 0.1134 0.1109 0.067 Uiso 1 1 calc R . .
C11 C 0.51781(17) 0.2615(2) 0.04687(12) 0.0590(5) Uani 1 1 d . . .
H11A H 0.4443 0.2534 0.0022 0.071 Uiso 1 1 calc R . .
H11B H 0.5477 0.3702 0.0511 0.071 Uiso 1 1 calc R . .
C12 C 0.77887(16) 0.0466(2) 0.23814(11) 0.0572(5) Uani 1 1 d . . .
H12A H 0.8264 -0.0494 0.2326 0.069 Uiso 1 1 calc R . .
H12B H 0.8362 0.1350 0.2350 0.069 Uiso 1 1 calc R . .
C13 C 0.74706(19) 0.0471(2) 0.31679(13) 0.0615(5) Uani 1 1 d . . .
C14 C 0.6045(3) -0.0532(4) 0.39264(17) 0.1109(11) Uani 1 1 d . . .
H14A H 0.6014 -0.1618 0.4096 0.133 Uiso 1 1 calc R A 1
H14B H 0.6660 0.0039 0.4327 0.133 Uiso 1 1 calc R A 1
C15A C 0.4761(6) 0.0173(11) 0.3815(4) 0.122(2) Uani 0.571(6) 1 d P B 1
H15A H 0.4229 -0.0167 0.3323 0.183 Uiso 0.571(6) 1 calc PR B 1
H15B H 0.4841 0.1302 0.3816 0.183 Uiso 0.571(6) 1 calc PR B 1
H15C H 0.4359 -0.0147 0.4231 0.183 Uiso 0.571(6) 1 calc PR B 1
C15B C 0.4853(9) -0.1059(14) 0.3848(6) 0.122(2) Uani 0.429(6) 1 d P B 2
H15D H 0.4251 -0.0345 0.3528 0.183 Uiso 0.429(6) 1 calc PR B 2
H15E H 0.4649 -0.1140 0.4353 0.183 Uiso 0.429(6) 1 calc PR B 2
H15F H 0.4781 -0.2081 0.3606 0.183 Uiso 0.429(6) 1 calc PR B 2
C16 C 0.3876(2) 0.3359(3) 0.14445(16) 0.0832(7) Uani 1 1 d . . .
H16A H 0.3536 0.2953 0.1870 0.125 Uiso 1 1 calc R . .
H16B H 0.3164 0.3595 0.1011 0.125 Uiso 1 1 calc R . .
H16C H 0.4368 0.4302 0.1608 0.125 Uiso 1 1 calc R . .
N1 N 0.62351(13) 0.15820(17) 0.03575(9) 0.0513(4) Uani 1 1 d . . .
O1 O 0.58872(11) 0.19546(14) 0.18220(7) 0.0538(4) Uani 1 1 d . . .
O2 O 0.64730(14) -0.0479(2) 0.31969(9) 0.0789(5) Uani 1 1 d . B .
O3 O 0.80566(18) 0.1200(2) 0.37129(10) 0.1042(6) Uani 1 1 d . . .
H7 H 0.855(2) -0.074(2) 0.0923(13) 0.069(6) Uiso 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 129.51(19) . . ?
N1 C1 C6 107.99(16) . . ?
C2 C1 C6 122.5(2) . . ?
C3 C2 C1 117.2(2) . . ?
C3 C2 H2 121.4 . . ?
C1 C2 H2 121.4 . . ?
C2 C3 C4 121.4(2) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C5 C4 C3 121.6(2) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C4 C5 C6 118.8(2) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C5 C6 C1 118.6(2) . . ?
C5 C6 C7 135.0(2) . . ?
C1 C6 C7 106.40(17) . . ?
C8 C7 C6 107.58(18) . . ?
C8 C7 H7 126.4(13) . . ?
C6 C7 H7 126.0(13) . . ?
C7 C8 N1 109.42(18) . . ?
C7 C8 C9 132.45(17) . . ?
N1 C8 C9 118.12(15) . . ?
O1 C9 C8 110.40(14) . . ?
O1 C9 C12 107.26(15) . . ?
C8 C9 C12 111.99(14) . . ?
O1 C9 H9 109.0 . . ?
C8 C9 H9 109.0 . . ?
C12 C9 H9 109.0 . . ?
O1 C10 C11 109.20(14) . . ?
O1 C10 C16 108.29(17) . . ?
C11 C10 C16 112.13(17) . . ?
O1 C10 H10 109.1 . . ?
C11 C10 H10 109.1 . . ?
C16 C10 H10 109.1 . . ?
N1 C11 C10 109.41(15) . . ?
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 . . ?
C13 C12 C9 114.11(15) . . ?
C13 C12 H12A 108.7 . . ?
C9 C12 H12A 108.7 . . ?
C13 C12 H12B 108.7 . . ?
C9 C12 H12B 108.7 . . ?
H12A C12 H12B 107.6 . . ?
O3 C13 O2 123.6(2) . . ?
O3 C13 C12 124.4(2) . . ?
O2 C13 C12 112.00(19) . . ?
C15B C14 C15A 44.5(4) . . ?
C15B C14 O2 113.3(5) . . ?
C15A C14 O2 109.3(3) . . ?
C15B C14 H14A 67.0 . . ?
C15A C14 H14A 109.8 . . ?
O2 C14 H14A 109.8 . . ?
C15B C14 H14B 135.4 . . ?
C15A C14 H14B 109.8 . . ?
O2 C14 H14B 109.8 . . ?
H14A C14 H14B 108.3 . . ?
C14 C15A H15A 109.5 . . ?
C14 C15A H15B 109.5 . . ?
C14 C15A H15C 109.5 . . ?
C14 C15B H15D 109.5 . . ?
C14 C15B H15E 109.5 . . ?
H15D C15B H15E 109.5 . . ?
C14 C15B H15F 109.5 . . ?
H15D C15B H15F 109.5 . . ?
H15E C15B H15F 109.5 . . ?
C10 C16 H16A 109.5 . . ?
C10 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C10 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C1 N1 C8 108.60(15) . . ?
C1 N1 C11 126.75(16) . . ?
C8 N1 C11 124.42(16) . . ?
C9 O1 C10 110.47(13) . . ?
C13 O2 C14 117.0(2) . . ?
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 1.371(2) . ?
C1 C2 1.389(3) . ?
C1 C6 1.404(3) . ?
C2 C3 1.370(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.394(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.365(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.400(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.425(3) . ?
C7 C8 1.355(3) . ?
C7 H7 0.91(2) . ?
C8 N1 1.377(2) . ?
C8 C9 1.493(3) . ?
C9 O1 1.428(2) . ?
C9 C12 1.523(3) . ?
C9 H9 0.9800 . ?
C10 O1 1.430(2) . ?
C10 C11 1.503(3) . ?
C10 C16 1.507(3) . ?
C10 H10 0.9800 . ?
C11 N1 1.458(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.491(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 O3 1.188(2) . ?
C13 O2 1.329(2) . ?
C14 C15B 1.305(9) . ?
C14 C15A 1.445(7) . ?
C14 O2 1.449(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15A H15A 0.9600 . ?
C15A H15B 0.9600 . ?
C15A H15C 0.9600 . ?
C15B H15D 0.9600 . ?
C15B H15E 0.9600 . ?
C15B H15F 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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 -178.41(19) . . . . ?
C6 C1 C2 C3 0.4(3) . . . . ?
C1 C2 C3 C4 0.4(4) . . . . ?
C2 C3 C4 C5 -0.9(4) . . . . ?
C3 C4 C5 C6 0.4(4) . . . . ?
C4 C5 C6 C1 0.4(3) . . . . ?
C4 C5 C6 C7 179.2(2) . . . . ?
N1 C1 C6 C5 178.24(17) . . . . ?
C2 C1 C6 C5 -0.8(3) . . . . ?
N1 C1 C6 C7 -0.87(19) . . . . ?
C2 C1 C6 C7 -179.93(19) . . . . ?
C5 C6 C7 C8 -178.7(2) . . . . ?
C1 C6 C7 C8 0.2(2) . . . . ?
C6 C7 C8 N1 0.5(2) . . . . ?
C6 C7 C8 C9 179.21(17) . . . . ?
C7 C8 C9 O1 157.52(18) . . . . ?
N1 C8 C9 O1 -23.9(2) . . . . ?
C7 C8 C9 C12 38.1(3) . . . . ?
N1 C8 C9 C12 -143.34(16) . . . . ?
O1 C10 C11 N1 47.76(19) . . . . ?
C16 C10 C11 N1 167.79(15) . . . . ?
O1 C9 C12 C13 55.9(2) . . . . ?
C8 C9 C12 C13 177.14(16) . . . . ?
C9 C12 C13 O3 -137.3(2) . . . . ?
C9 C12 C13 O2 44.6(2) . . . . ?
C2 C1 N1 C8 -179.82(19) . . . . ?
C6 C1 N1 C8 1.21(19) . . . . ?
C2 C1 N1 C11 -5.2(3) . . . . ?
C6 C1 N1 C11 175.80(15) . . . . ?
C7 C8 N1 C1 -1.09(19) . . . . ?
C9 C8 N1 C1 -179.99(14) . . . . ?
C7 C8 N1 C11 -175.84(15) . . . . ?
C9 C8 N1 C11 5.3(2) . . . . ?
C10 C11 N1 C1 169.27(16) . . . . ?
C10 C11 N1 C8 -17.0(2) . . . . ?
C8 C9 O1 C10 57.05(17) . . . . ?
C12 C9 O1 C10 179.32(14) . . . . ?
C11 C10 O1 C9 -71.37(18) . . . . ?
C16 C10 O1 C9 166.26(16) . . . . ?
O3 C13 O2 C14 3.9(3) . . . . ?
C12 C13 O2 C14 -177.99(18) . . . . ?
C15B C14 O2 C13 159.5(6) . . . . ?
C15A C14 O2 C13 111.7(4) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139181772
