#------------------------------------------------------------------------------
#$Date: 2023-08-24 04:43:32 +0300 (Thu, 24 Aug 2023) $
#$Revision: 285854 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/28/2022840.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2022840
loop_
_publ_author_name
'Flores, Maritza J.'
'Mai, Brandon'
'Tanski, Joseph M.'
_publ_section_title
;
 Spectroscopic, crystallographic, and Hirshfeld surface characterization
 of nine-membered-ring-containing
 9-methoxy-3,4,5,6-tetrahydro-1H-benzo[b]azonine-2,7-dione and its parent
 tetrahydrocarbazole
;
_journal_coeditor_code           DX2054
_journal_issue                   9
_journal_name_full
'Acta Crystallographica Section E Crystallographic Communications'
_journal_paper_doi               10.1107/S2056989023007259
_journal_volume                  79
_journal_year                    2023
_chemical_formula_iupac          'C13 H15 N O3'
_chemical_formula_moiety         'C13 H15 N O3'
_chemical_formula_sum            'C13 H15 N O3'
_chemical_formula_weight         233.26
_chemical_name_systematic
;
9-Methoxy-3,4,5,6-tetrahydro-1H-benzo[b]azonine-2,7-dione
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 96.4840(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.0139(8)
_cell_length_b                   8.2743(4)
_cell_length_c                   8.5596(4)
_cell_measurement_reflns_used    9966
_cell_measurement_temperature    125.(2)
_cell_measurement_theta_max      30.5027
_cell_measurement_theta_min      2.5601
_cell_volume                     1126.92(9)
_computing_cell_refinement
;
SAINT (Bruker, 2013)
;
_computing_data_collection
;
APEX2 (Bruker, 2013)
;
_computing_data_reduction
;
SAINT (Bruker, 2013)
;
_computing_molecular_graphics
;
SHELXTL2014 (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXTL2014 (Sheldrick, 2008), OLEX2 (Dolomanov et al.,
2009), and
Mercury (Macrae et al.,  2020)
;
_computing_structure_refinement
;
SHELXL2017 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2018 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      125.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            27192
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         30.53
_diffrn_reflns_theta_min         2.56
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.50
_diffrn_source_voltage           45
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2013)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.190
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         3432
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0401
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0545P)²+0.3033P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0997
_refine_ls_wR_factor_ref         0.1099
_reflns_number_gt                2685
_reflns_number_total             3432
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            dx2054sup1.cif
_cod_data_source_block           I
_cod_database_code               2022840
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.11242(5) 0.38292(11) 0.51840(9) 0.02220(19) Uani d 1 . .
O O2 0.27855(6) 0.62150(11) 0.56201(10) 0.0280(2) Uani d 1 . .
O O3 0.47875(5) 0.12590(10) 0.65022(10) 0.0253(2) Uani d 1 . .
N N1 0.16638(6) 0.25619(12) 0.31640(10) 0.01783(19) Uani d 1 . .
H H1 0.1564(9) 0.2229(17) 0.2199(14) 0.021 Uiso d 1 . .
C C1 0.10773(7) 0.34800(14) 0.37727(12) 0.0177(2) Uani d 1 . .
C C2 0.04082(7) 0.41965(15) 0.26000(13) 0.0213(2) Uani d 1 . .
H H2A -0.005196 0.463892 0.31533 0.026 Uiso calc 1 . .
H H2B 0.017052 0.33484 0.186381 0.026 Uiso calc 1 . .
C C3 0.07963(7) 0.55581(15) 0.16766(13) 0.0217(2) Uani d 1 . .
H H3A 0.106874 0.50615 0.081181 0.026 Uiso calc 1 . .
H H3B 0.033617 0.625756 0.119347 0.026 Uiso calc 1 . .
C C4 0.14461(7) 0.66276(14) 0.26519(13) 0.0218(2) Uani d 1 . .
H H4A 0.125394 0.681824 0.369587 0.026 Uiso calc 1 . .
H H4B 0.147046 0.768829 0.21239 0.026 Uiso calc 1 . .
C C5 0.23445(7) 0.58971(14) 0.28901(13) 0.0204(2) Uani d 1 . .
H H5A 0.236483 0.499036 0.214073 0.024 Uiso calc 1 . .
H H5B 0.274181 0.67316 0.259799 0.024 Uiso calc 1 . .
C C6 0.26634(7) 0.52791(14) 0.45201(13) 0.0181(2) Uani d 1 . .
C C7 0.29362(7) 0.35427(13) 0.47129(12) 0.0163(2) Uani d 1 . .
C C8 0.37105(7) 0.32367(13) 0.55989(12) 0.0181(2) Uani d 1 . .
H H8 0.401666 0.409546 0.613125 0.022 Uiso calc 1 . .
C C9 0.40292(7) 0.16727(14) 0.56963(12) 0.0186(2) Uani d 1 . .
C C10 0.35732(7) 0.04099(14) 0.49279(13) 0.0208(2) Uani d 1 . .
H H10 0.379971 -0.065242 0.496916 0.025 Uiso calc 1 . .
C C11 0.27931(7) 0.06986(14) 0.41066(13) 0.0196(2) Uani d 1 . .
H H11 0.247791 -0.017201 0.361538 0.024 Uiso calc 1 . .
C C12 0.24680(6) 0.22611(13) 0.39972(12) 0.0161(2) Uani d 1 . .
C C13 0.52750(8) 0.25286(16) 0.72746(15) 0.0268(3) Uani d 1 . .
H H13A 0.540945 0.332863 0.649661 0.04 Uiso calc 1 . .
H H13B 0.579679 0.20819 0.78132 0.04 Uiso calc 1 . .
H H13C 0.495377 0.304782 0.804483 0.04 Uiso calc 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C9 O3 C13 . . 117.19(9) ?
C1 N1 C12 . . 122.17(9) ?
C1 N1 H1 . . 118.8(9) ?
C12 N1 H1 . . 118.8(9) ?
O1 C1 N1 . . 122.53(10) ?
O1 C1 C2 . . 121.33(10) ?
N1 C1 C2 . . 115.85(9) ?
C1 C2 C3 . . 109.33(9) ?
C1 C2 H2A . . 109.8 ?
C3 C2 H2A . . 109.8 ?
C1 C2 H2B . . 109.8 ?
C3 C2 H2B . . 109.8 ?
H2A C2 H2B . . 108.3 ?
C4 C3 C2 . . 115.34(9) ?
C4 C3 H3A . . 108.4 ?
C2 C3 H3A . . 108.4 ?
C4 C3 H3B . . 108.4 ?
C2 C3 H3B . . 108.4 ?
H3A C3 H3B . . 107.5 ?
C3 C4 C5 . . 114.03(10) ?
C3 C4 H4A . . 108.7 ?
C5 C4 H4A . . 108.7 ?
C3 C4 H4B . . 108.7 ?
C5 C4 H4B . . 108.7 ?
H4A C4 H4B . . 107.6 ?
C6 C5 C4 . . 117.52(9) ?
C6 C5 H5A . . 107.9 ?
C4 C5 H5A . . 107.9 ?
C6 C5 H5B . . 107.9 ?
C4 C5 H5B . . 107.9 ?
H5A C5 H5B . . 107.2 ?
O2 C6 C7 . . 120.19(10) ?
O2 C6 C5 . . 120.27(10) ?
C7 C6 C5 . . 119.03(9) ?
C12 C7 C8 . . 119.84(10) ?
C12 C7 C6 . . 122.73(9) ?
C8 C7 C6 . . 117.38(9) ?
C9 C8 C7 . . 119.81(10) ?
C9 C8 H8 . . 120.1 ?
C7 C8 H8 . . 120.1 ?
O3 C9 C8 . . 124.13(10) ?
O3 C9 C10 . . 115.90(10) ?
C8 C9 C10 . . 119.97(10) ?
C11 C10 C9 . . 120.30(10) ?
C11 C10 H10 . . 119.9 ?
C9 C10 H10 . . 119.9 ?
C10 C11 C12 . . 120.24(10) ?
C10 C11 H11 . . 119.9 ?
C12 C11 H11 . . 119.9 ?
C11 C12 C7 . . 119.74(10) ?
C11 C12 N1 . . 120.44(10) ?
C7 C12 N1 . . 119.81(10) ?
O3 C13 H13A . . 109.5 ?
O3 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
O3 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . 1.2361(13) ?
O2 C6 . 1.2177(13) ?
O3 C9 . 1.3705(13) ?
O3 C13 . 1.4260(15) ?
N1 C1 . 1.3570(14) ?
N1 C12 . 1.4218(14) ?
N1 H1 . 0.869(12) ?
C1 C2 . 1.5047(15) ?
C2 C3 . 1.5463(17) ?
C2 H2A . 0.99 ?
C2 H2B . 0.99 ?
C3 C4 . 1.5384(16) ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C4 C5 . 1.5526(16) ?
C4 H4A . 0.99 ?
C4 H4B . 0.99 ?
C5 C6 . 1.5192(15) ?
C5 H5A . 0.99 ?
C5 H5B . 0.99 ?
C6 C7 . 1.5053(15) ?
C7 C12 . 1.3995(15) ?
C7 C8 . 1.4015(15) ?
C8 C9 . 1.3901(16) ?
C8 H8 . 0.95 ?
C9 C10 . 1.3961(16) ?
C10 C11 . 1.3834(16) ?
C10 H10 . 0.95 ?
C11 C12 . 1.3930(15) ?
C11 H11 . 0.95 ?
C13 H13A . 0.98 ?
C13 H13B . 0.98 ?
C13 H13C . 0.98 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 O1 4_565 0.869(12) 1.990(12) 2.8426(12) 166.7(14) y
C5 H5B O2 4_575 0.99 2.41 3.2085(14) 138 y
C13 H13B O2 2_646 0.98 2.60 3.5793(15) 174 y
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C12 N1 C1 O1 . . . . -15.63(16) ?
C12 N1 C1 C2 . . . . 158.31(10) ?
O1 C1 C2 C3 . . . . 102.43(12) ?
N1 C1 C2 C3 . . . . -71.59(13) ?
C1 C2 C3 C4 . . . . -38.86(13) ?
C2 C3 C4 C5 . . . . 82.68(12) ?
C3 C4 C5 C6 . . . . -108.22(11) ?
C4 C5 C6 O2 . . . . -65.85(14) ?
C4 C5 C6 C7 . . . . 122.35(11) ?
O2 C6 C7 C12 . . . . 142.88(11) ?
C5 C6 C7 C12 . . . . -45.31(14) ?
O2 C6 C7 C8 . . . . -39.79(15) ?
C5 C6 C7 C8 . . . . 132.02(10) ?
C12 C7 C8 C9 . . . . 3.25(16) ?
C6 C7 C8 C9 . . . . -174.16(10) ?
C13 O3 C9 C8 . . . . -0.42(16) ?
C13 O3 C9 C10 . . . . 178.85(10) ?
C7 C8 C9 O3 . . . . 178.48(10) ?
C7 C8 C9 C10 . . . . -0.76(16) ?
O3 C9 C10 C11 . . . . 178.79(10) ?
C8 C9 C10 C11 . . . . -1.91(16) ?
C9 C10 C11 C12 . . . . 2.07(17) ?
C10 C11 C12 C7 . . . . 0.44(16) ?
C10 C11 C12 N1 . . . . -179.54(10) ?
C8 C7 C12 C11 . . . . -3.09(15) ?
C6 C7 C12 C11 . . . . 174.17(10) ?
C8 C7 C12 N1 . . . . 176.89(9) ?
C6 C7 C12 N1 . . . . -5.85(15) ?
C1 N1 C12 C11 . . . . 132.57(11) ?
C1 N1 C12 C7 . . . . -47.40(14) ?

_cod_database_fobs_code 2022840
