#------------------------------------------------------------------------------
#$Date: 2025-08-23 00:12:46 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301866 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/53/7235303.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_7235303
loop_
_publ_author_name
'Borah, Ruli'
'Dutta, Arup Kumar'
'Sarma, Parishmita'
'Dutta, Champak'
'Sarma, Bipul'
_publ_section_title
;
 Synthesis of anti-2,3-dihydro-1,2,3-trisubstituted-1H-naphth
 [1,2-e][1,3]oxazine derivatives via multicomponent approach
;
_journal_issue                   21
_journal_name_full               'RSC Advances'
_journal_page_first              10912
_journal_paper_doi               10.1039/c3ra47211f
_journal_volume                  4
_journal_year                    2014
_chemical_formula_sum            'C28 H27 N O'
_chemical_formula_weight         393.51
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                96.088(3)
_cell_angle_beta                 98.252(3)
_cell_angle_gamma                97.358(3)
_cell_formula_units_Z            2
_cell_length_a                   8.8634(4)
_cell_length_b                   10.7499(5)
_cell_length_c                   11.8110(6)
_cell_measurement_reflns_used    3651
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.94
_cell_measurement_theta_min      2.35
_cell_volume                     1095.62(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and 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  0.0316
_diffrn_reflns_av_sigmaI/netI    0.0298
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13783
_diffrn_reflns_theta_full        24.48
_diffrn_reflns_theta_max         24.48
_diffrn_reflns_theta_min         1.76
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.9845
_exptl_absorpt_correction_T_min  0.9706
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         3627
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0478
_refine_ls_shift/su_max          3.295
_refine_ls_shift/su_mean         0.021
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1037P)²+0.0640P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1377
_refine_ls_wR_factor_ref         0.1713
_reflns_number_gt                2536
_reflns_number_total             3627
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ra47211f2.cif
_cod_data_source_block           bs_arup1_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Triclinic' was changed to
'triclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7235303
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
O1 O 0.08564(14) 0.20044(12) 0.60100(11) 0.0563(4) Uani 1 1 d .
N1 N 0.16144(16) 0.37450(13) 0.75187(13) 0.0472(4) Uani 1 1 d .
C11 C 0.3446(2) 0.30831(16) 0.62714(17) 0.0484(5) Uani 1 1 d .
C1 C -0.0719(2) 0.22255(16) 0.75049(17) 0.0485(5) Uani 1 1 d .
C2 C -0.2150(2) 0.18377(17) 0.78802(18) 0.0536(5) Uani 1 1 d .
C9 C -0.1608(2) 0.08248(18) 0.57098(19) 0.0608(6) Uani 1 1 d .
H9 H -0.1418 0.0495 0.4992 0.073 Uiso 1 1 calc R
C10 C 0.2096(2) 0.27056(17) 0.68640(17) 0.0482(5) Uani 1 1 d .
H10 H 0.242(2) 0.2124(18) 0.7406(16) 0.058 Uiso 1 1 calc .
C17 C 0.0501(2) 0.32294(16) 0.82343(16) 0.0491(5) Uani 1 1 d .
H17 H -0.0025 0.3925 0.8504 0.059 Uiso 1 1 calc R
C7 C -0.3286(2) 0.09389(19) 0.7143(2) 0.0607(6) Uani 1 1 d .
C18 C 0.1361(2) 0.27967(17) 0.92942(16) 0.0497(5) Uani 1 1 d .
C3 C -0.2490(2) 0.2298(2) 0.8966(2) 0.0664(6) Uani 1 1 d .
H3 H -0.1765 0.2887 0.9461 0.080 Uiso 1 1 calc R
C23 C 0.1225(2) 0.15533(18) 0.95040(17) 0.0559(5) Uani 1 1 d .
H23 H 0.0558 0.0944 0.8987 0.067 Uiso 1 1 calc R
C16 C 0.4792(2) 0.37089(19) 0.69563(19) 0.0602(6) Uani 1 1 d .
H16 H 0.4809 0.3920 0.7743 0.072 Uiso 1 1 calc R
C24 C 0.1040(2) 0.46906(17) 0.68258(17) 0.0548(5) Uani 1 1 d .
H24A H -0.0054 0.4443 0.6554 0.066 Uiso 1 1 calc R
H24B H 0.1557 0.4716 0.6156 0.066 Uiso 1 1 calc R
C12 C 0.3449(2) 0.2783(2) 0.51148(19) 0.0629(6) Uani 1 1 d .
H12 H 0.2559 0.2367 0.4641 0.075 Uiso 1 1 calc R
C8 C -0.2972(2) 0.04603(19) 0.6060(2) 0.0648(6) Uani 1 1 d .
H8 H -0.3716 -0.0119 0.5572 0.078 Uiso 1 1 calc R
C6 C -0.4687(2) 0.0548(2) 0.7529(3) 0.0775(7) Uani 1 1 d .
H6 H -0.5435 -0.0035 0.7049 0.093 Uiso 1 1 calc R
C4 C -0.3862(3) 0.1893(3) 0.9301(2) 0.0837(8) Uani 1 1 d .
H4 H -0.4064 0.2215 1.0018 0.100 Uiso 1 1 calc R
C13 C 0.4778(3) 0.3097(2) 0.4648(2) 0.0763(7) Uani 1 1 d .
H13 H 0.4772 0.2891 0.3862 0.092 Uiso 1 1 calc R
C25 C 0.1305(3) 0.59984(19) 0.7506(2) 0.0707(6) Uani 1 1 d .
H25A H 0.0846 0.5954 0.8201 0.085 Uiso 1 1 calc R
H25B H 0.2404 0.6259 0.7738 0.085 Uiso 1 1 calc R
C14 C 0.6094(3) 0.3705(2) 0.5333(2) 0.0731(7) Uani 1 1 d .
H14 H 0.6983 0.3904 0.5018 0.088 Uiso 1 1 calc R
C15 C 0.6096(2) 0.4018(2) 0.6484(2) 0.0694(6) Uani 1 1 d .
H15 H 0.6987 0.4443 0.6950 0.083 Uiso 1 1 calc R
C22 C 0.2054(3) 0.1192(2) 1.0462(2) 0.0707(6) Uani 1 1 d .
H22 H 0.1948 0.0346 1.0582 0.085 Uiso 1 1 calc R
C5 C -0.4966(3) 0.1001(3) 0.8580(3) 0.0868(8) Uani 1 1 d .
H5 H -0.5890 0.0720 0.8820 0.104 Uiso 1 1 calc R
C26 C 0.0655(3) 0.6976(2) 0.6858(2) 0.0915(8) Uani 1 1 d .
H26A H -0.0451 0.6731 0.6654 0.110 Uiso 1 1 calc R
H26B H 0.1079 0.6992 0.6146 0.110 Uiso 1 1 calc R
C19 C 0.2376(3) 0.3676(2) 1.0089(2) 0.0780(7) Uani 1 1 d .
H19 H 0.2504 0.4522 0.9970 0.094 Uiso 1 1 calc R
C21 C 0.3033(3) 0.2074(3) 1.1237(2) 0.0847(8) Uani 1 1 d .
H21 H 0.3585 0.1831 1.1888 0.102 Uiso 1 1 calc R
C27 C 0.0964(4) 0.8285(2) 0.7500(3) 0.1100(10) Uani 1 1 d .
H27A H 0.0514 0.8290 0.8192 0.165 Uiso 1 1 calc R
H27B H 0.0520 0.8857 0.7023 0.165 Uiso 1 1 calc R
H27C H 0.2056 0.8546 0.7695 0.165 Uiso 1 1 calc R
C20 C 0.3197(3) 0.3309(3) 1.1054(2) 0.0954(9) Uani 1 1 d .
H20 H 0.3865 0.3909 1.1581 0.115 Uiso 1 1 calc R
C28 C -0.0481(2) 0.17095(17) 0.64461(17) 0.0505(5) 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
C28 O1 C10 113.06(14)
C10 N1 C24 114.35(15)
C10 N1 C17 108.44(13)
C24 N1 C17 113.16(14)
C12 C11 C16 118.56(18)
C12 C11 C10 123.83(18)
C16 C11 C10 117.50(18)
C28 C1 C2 118.71(17)
C28 C1 C17 119.89(16)
C2 C1 C17 121.36(17)
C3 C2 C7 117.90(19)
C3 C2 C1 122.82(19)
C7 C2 C1 119.28(19)
C8 C9 C28 119.3(2)
C8 C9 H9 120.3
C28 C9 H9 120.3
N1 C10 O1 112.49(14)
N1 C10 C11 113.85(14)
O1 C10 C11 108.49(15)
N1 C10 H10 104.6(10)
O1 C10 H10 107.0(10)
C11 C10 H10 110.2(10)
N1 C17 C18 109.74(14)
N1 C17 C1 110.24(15)
C18 C17 C1 114.86(15)
N1 C17 H17 107.2
C18 C17 H17 107.2
C1 C17 H17 107.2
C8 C7 C6 122.2(2)
C8 C7 C2 118.99(18)
C6 C7 C2 118.8(2)
C23 C18 C19 117.27(19)
C23 C18 C17 123.25(17)
C19 C18 C17 119.45(17)
C4 C3 C2 121.2(2)
C4 C3 H3 119.4
C2 C3 H3 119.4
C18 C23 C22 121.6(2)
C18 C23 H23 119.2
C22 C23 H23 119.2
C15 C16 C11 120.7(2)
C15 C16 H16 119.7
C11 C16 H16 119.7
N1 C24 C25 112.07(17)
N1 C24 H24A 109.2
C25 C24 H24A 109.2
N1 C24 H24B 109.2
C25 C24 H24B 109.2
H24A C24 H24B 107.9
C11 C12 C13 120.2(2)
C11 C12 H12 119.9
C13 C12 H12 119.9
C9 C8 C7 121.5(2)
C9 C8 H8 119.2
C7 C8 H8 119.2
C5 C6 C7 121.6(2)
C5 C6 H6 119.2
C7 C6 H6 119.2
C3 C4 C5 120.7(2)
C3 C4 H4 119.7
C5 C4 H4 119.7
C14 C13 C12 120.5(2)
C14 C13 H13 119.7
C12 C13 H13 119.7
C26 C25 C24 114.0(2)
C26 C25 H25A 108.8
C24 C25 H25A 108.8
C26 C25 H25B 108.8
C24 C25 H25B 108.8
H25A C25 H25B 107.7
C15 C14 C13 119.7(2)
C15 C14 H14 120.2
C13 C14 H14 120.2
C14 C15 C16 120.4(2)
C14 C15 H15 119.8
C16 C15 H15 119.8
C21 C22 C23 120.1(2)
C21 C22 H22 119.9
C23 C22 H22 119.9
C6 C5 C4 119.8(2)
C6 C5 H5 120.1
C4 C5 H5 120.1
C25 C26 C27 114.6(2)
C25 C26 H26A 108.6
C27 C26 H26A 108.6
C25 C26 H26B 108.6
C27 C26 H26B 108.6
H26A C26 H26B 107.6
C20 C19 C18 120.9(2)
C20 C19 H19 119.6
C18 C19 H19 119.6
C20 C21 C22 119.8(2)
C20 C21 H21 120.1
C22 C21 H21 120.1
C26 C27 H27A 109.5
C26 C27 H27B 109.5
H27A C27 H27B 109.5
C26 C27 H27C 109.5
H27A C27 H27C 109.5
H27B C27 H27C 109.5
C21 C20 C19 120.4(2)
C21 C20 H20 119.8
C19 C20 H20 119.8
C1 C28 O1 123.39(16)
C1 C28 C9 122.15(18)
O1 C28 C9 114.45(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C28 1.372(2)
O1 C10 1.449(2)
N1 C10 1.436(2)
N1 C24 1.467(2)
N1 C17 1.481(2)
C11 C12 1.371(3)
C11 C16 1.390(3)
C11 C10 1.504(3)
C1 C28 1.369(3)
C1 C2 1.430(3)
C1 C17 1.521(3)
C2 C3 1.412(3)
C2 C7 1.424(3)
C9 C8 1.357(3)
C9 C28 1.411(3)
C9 H9 0.9300
C10 H10 1.030(19)
C17 C18 1.518(3)
C17 H17 0.9800
C7 C8 1.407(3)
C7 C6 1.413(3)
C18 C23 1.378(3)
C18 C19 1.391(3)
C3 C4 1.366(3)
C3 H3 0.9300
C23 C22 1.379(3)
C23 H23 0.9300
C16 C15 1.373(3)
C16 H16 0.9300
C24 C25 1.516(3)
C24 H24A 0.9700
C24 H24B 0.9700
C12 C13 1.389(3)
C12 H12 0.9300
C8 H8 0.9300
C6 C5 1.352(4)
C6 H6 0.9300
C4 C5 1.397(4)
C4 H4 0.9300
C13 C14 1.365(3)
C13 H13 0.9300
C25 C26 1.490(3)
C25 H25A 0.9700
C25 H25B 0.9700
C14 C15 1.364(3)
C14 H14 0.9300
C15 H15 0.9300
C22 C21 1.366(3)
C22 H22 0.9300
C5 H5 0.9300
C26 C27 1.498(4)
C26 H26A 0.9700
C26 H26B 0.9700
C19 C20 1.385(3)
C19 H19 0.9300
C21 C20 1.360(4)
C21 H21 0.9300
C27 H27A 0.9600
C27 H27B 0.9600
C27 H27C 0.9600
C20 H20 0.9300
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139075412
