##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_global
_audit_creation_method     'APEX3 v2019.11-0'
_journal_date_recd_electronic     2023-07-24
_journal_date_accepted     2023-08-17
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2023
_journal_volume     79
_journal_issue      9
_journal_page_first     831
_journal_page_last     836
_journal_paper_category     GO
_journal_paper_doi     10.1107/S2056989023007259
_journal_coeditor_code     DX2054
_publ_contact_author_name     'Joseph M. Tanski'
_publ_contact_author_address
;
Department of Chemistry
Vassar College
Poughkeepsie, NY 12604
USA
;
_publ_contact_author_email     'jotanski@vassar.edu'
_publ_contact_author_fax     '845-437-5747'
_publ_contact_author_phone     '845-437-5731'
_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
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Flores, Maritza J.' .
;
Department of Chemistry
Vassar College
Poughkeepsie
NY 12604
USA
;
    'Mai, Brandon' .
;
Department of Chemistry
Vassar College
Poughkeepsie
NY 12604
USA
;
    'Tanski, Joseph M.' .
;
Department of Chemistry
Vassar College
Poughkeepsie
NY 12604
USA
;
_publ_section_synopsis
;
9-Methoxy-3,4,5,6-tetrahydro-1H-benzo[b]azonine-2,7-dione and
6-methoxy-1,2,3,4-tetrahydrocarbazole represent the structures of a
benzoazonine that contains a nine-membered ring and its parent
tetrahydrocarbazole. The molecules of the former pack together via
strong amide N---H...O hydrogen bonding and weak C---H...O interactions,
whereas the parent tetrahydrocarbazole packs with C/N---H...π interactions,
as visualized by Hirshfeld surface characterization.
;
data_I
_chemical_name_systematic
;
9-Methoxy-3,4,5,6-tetrahydro-1H-benzo[b]azonine-2,7-dione
;
_chemical_name_common     ?
_chemical_formula_moiety     'C13 H15 N O3'
_chemical_formula_sum     'C13 H15 N O3'
_chemical_formula_iupac     'C13 H15 N O3'
_chemical_formula_weight     233.26
_chemical_melting_point     ?
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 1 21/c 1'
_space_group_name_Hall     '-P 2ybc'
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'
_cell_length_a     16.0139(8)
_cell_length_b     8.2743(4)
_cell_length_c     8.5596(4)
_cell_angle_alpha     90
_cell_angle_beta     96.4840(10)
_cell_angle_gamma     90
_cell_volume     1126.92(9)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     9966
_cell_measurement_theta_min     2.5601
_cell_measurement_theta_max     30.5027
_cell_measurement_temperature     125.(2)
_exptl_crystal_description     needle
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.400
_exptl_crystal_size_mid     0.100
_exptl_crystal_size_min     0.030
_exptl_crystal_density_diffrn     1.375
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     496
_exptl_absorpt_coefficient_mu     0.098
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2013)
;
_exptl_absorpt_correction_T_min     0.91
_exptl_absorpt_correction_T_max     1.00
_exptl_special_details
;
;
_diffrn_ambient_temperature     125.(2)
_diffrn_source     'sealed X-ray tube'
_diffrn_source_power     1.50
_diffrn_source_voltage     45
_diffrn_source_current     30.0
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker APEXII CCD'
_diffrn_measurement_device     'three-circle diffractometer'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     8.3333
_diffrn_reflns_number     27192
_diffrn_reflns_av_R_equivalents     0.0384
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_theta_min     2.56
_diffrn_reflns_theta_max     30.53
_diffrn_reflns_theta_full     25.24
_diffrn_measured_fraction_theta_max     0.997
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -22
_diffrn_reflns_limit_h_max     22
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -12
_diffrn_reflns_limit_l_max     12
_diffrn_radiation_probe     x-ray
_refine_special_details
;
;
_reflns_number_total     3432
_reflns_number_gt     2685
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0559
_refine_ls_R_factor_gt     0.0401
_refine_ls_wR_factor_gt     0.0997
_refine_ls_wR_factor_ref     0.1099
_refine_ls_goodness_of_fit_ref     1.044
_refine_ls_restrained_S_all     1.044
_refine_ls_number_reflns     3432
_refine_ls_number_parameters     158
_refine_ls_number_restraints     1
_refine_ls_number_constraints     ?
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0545P)²+0.3033P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.374
_refine_diff_density_min     -0.190
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection
;
APEX2 (Bruker, 2013)
;
_computing_cell_refinement
;
SAINT (Bruker, 2013)
;
_computing_data_reduction
;
SAINT (Bruker, 2013)
;
_computing_structure_solution
;
SHELXT2018 (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL2017 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
SHELXTL2014 (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXTL2014 (Sheldrick, 2008), OLEX2 (Dolomanov et al.,
2009), and
Mercury (Macrae et al.,  2020)
;
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 . .
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
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_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_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) ?
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
data_II
_chemical_name_systematic
;
6-Methoxy-1,2,3,4-tetrahydrocarbazole
;
_chemical_name_common     ?
_chemical_formula_moiety     'C13 H15 N O'
_chemical_formula_sum     'C13 H15 N O'
_chemical_formula_iupac     'C13 H15 N O'
_chemical_formula_weight     201.26
_chemical_melting_point     ?
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'C 1 2/c 1'
_space_group_name_Hall     '-C 2yc'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, y, -z+1/2'
    'x+1/2, y+1/2, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y, z-1/2'
    '-x+1/2, -y+1/2, -z'
    'x+1/2, -y+1/2, z-1/2'
_cell_length_a     20.513(2)
_cell_length_b     5.6374(6)
_cell_length_c     18.783(2)
_cell_angle_alpha     90
_cell_angle_beta     100.757(2)
_cell_angle_gamma     90
_cell_volume     2133.9(4)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     7271
_cell_measurement_theta_min     2.2073
_cell_measurement_theta_max     30.5219
_cell_measurement_temperature     125.(2)
_exptl_crystal_description     block
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.210
_exptl_crystal_size_mid     0.100
_exptl_crystal_size_min     0.100
_exptl_crystal_density_diffrn     1.253
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     864
_exptl_absorpt_coefficient_mu     0.079
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2013)
;
_exptl_absorpt_correction_T_min     0.93
_exptl_absorpt_correction_T_max     0.99
_exptl_special_details
;
;
_diffrn_ambient_temperature     125.(2)
_diffrn_source     'sealed X-ray tube'
_diffrn_source_power     1.50
_diffrn_source_voltage     50
_diffrn_source_current     30.0
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker APEXII CCD'
_diffrn_measurement_device     'three-circle diffractometer'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     8.3333
_diffrn_reflns_number     24248
_diffrn_reflns_av_R_equivalents     0.0303
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_theta_min     2.02
_diffrn_reflns_theta_max     30.53
_diffrn_reflns_theta_full     25.24
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -29
_diffrn_reflns_limit_h_max     29
_diffrn_reflns_limit_k_min     -8
_diffrn_reflns_limit_k_max     8
_diffrn_reflns_limit_l_min     -26
_diffrn_reflns_limit_l_max     26
_diffrn_radiation_probe     x-ray
_refine_special_details
;
;
_reflns_number_total     3249
_reflns_number_gt     2619
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0540
_refine_ls_R_factor_gt     0.0415
_refine_ls_wR_factor_gt     0.1082
_refine_ls_wR_factor_ref     0.1166
_refine_ls_goodness_of_fit_ref     1.032
_refine_ls_restrained_S_all     1.031
_refine_ls_number_reflns     3249
_refine_ls_number_parameters     140
_refine_ls_number_restraints     1
_refine_ls_number_constraints     ?
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0616P)²+1.0160P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.418
_refine_diff_density_min     -0.178
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection
;
APEX2 (Bruker, 2013)
;
_computing_cell_refinement
;
SAINT (Bruker, 2013)
;
_computing_data_reduction
;
SAINT (Bruker, 2013)
;
_computing_structure_solution
;
SHELXT2018 (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL2017 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
SHELXTL2014 (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXTL2014 (Sheldrick, 2008), OLEX2 (Dolomanov et al.,
2009), and
Mercury (Macrae et al.,  2020)
;
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 0.87890(4) 0.58856(15) 0.58257(5) 0.0314(2) Uani d 1 . .
    N N1 0.68765(4) 1.06336(16) 0.69736(5) 0.02345(19) Uani d 1 . .
    H H1 0.6884(6) 1.180(2) 0.7285(7) 0.028 Uiso d 1 . .
    C C1 0.63171(5) 0.93481(17) 0.66796(5) 0.0209(2) Uani d 1 . .
    C C2 0.56378(5) 0.97953(19) 0.68306(6) 0.0262(2) Uani d 1 . .
    H H2A 0.543971 1.11983 0.655501 0.031 Uiso calc 1 . .
    H H2B 0.566248 1.011127 0.735341 0.031 Uiso calc 1 . .
    C C3 0.52072(5) 0.7590(2) 0.66027(6) 0.0269(2) Uani d 1 . .
    H H3A 0.533725 0.631075 0.696225 0.032 Uiso calc 1 . .
    H H3B 0.473584 0.798258 0.659681 0.032 Uiso calc 1 . .
    C C4 0.52847(5) 0.6710(2) 0.58520(6) 0.0275(2) Uani d 1 . .
    H H4A 0.516861 0.800874 0.549615 0.033 Uiso calc 1 . .
    H H4B 0.497181 0.538507 0.570449 0.033 Uiso calc 1 . .
    C C5 0.59931(5) 0.58670(19) 0.58405(6) 0.0232(2) Uani d 1 . .
    H H5A 0.606042 0.426696 0.605908 0.028 Uiso calc 1 . .
    H H5B 0.606091 0.57628 0.533321 0.028 Uiso calc 1 . .
    C C6 0.64860(5) 0.75580(17) 0.62552(5) 0.01940(19) Uani d 1 . .
    C C7 0.71886(5) 0.76989(17) 0.62904(5) 0.01899(19) Uani d 1 . .
    C C8 0.76363(5) 0.63638(18) 0.59683(5) 0.0215(2) Uani d 1 . .
    H H8A 0.74878 0.505574 0.566186 0.026 Uiso calc 1 . .
    C C9 0.83002(5) 0.70122(18) 0.61111(5) 0.0229(2) Uani d 1 . .
    C C10 0.85231(5) 0.89428(19) 0.65691(6) 0.0246(2) Uani d 1 . .
    H H10A 0.898194 0.93291 0.666406 0.03 Uiso calc 1 . .
    C C11 0.80883(5) 1.02892(18) 0.68837(6) 0.0241(2) Uani d 1 . .
    H H11A 0.824024 1.160428 0.718572 0.029 Uiso calc 1 . .
    C C12 0.74189(5) 0.96489(17) 0.67422(5) 0.02058(19) Uani d 1 . .
    C C13 0.85810(6) 0.4022(2) 0.53217(6) 0.0298(2) Uani d 1 . .
    H H13A 0.896092 0.346117 0.512031 0.045 Uiso calc 1 . .
    H H13B 0.823643 0.461442 0.492906 0.045 Uiso calc 1 . .
    H H13C 0.840275 0.271001 0.556907 0.045 Uiso calc 1 . .
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C9 . 1.3772(12) ?
    O1 C13 . 1.4251(15) ?
    N1 C1 . 1.3822(13) ?
    N1 C12 . 1.3841(13) ?
    N1 H1 . 0.878(12) ?
    C1 C6 . 1.3700(14) ?
    C1 C2 . 1.4944(14) ?
    C2 C3 . 1.5387(15) ?
    C2 H2A . 0.99 ?
    C2 H2B . 0.99 ?
    C3 C4 . 1.5309(15) ?
    C3 H3A . 0.99 ?
    C3 H3B . 0.99 ?
    C4 C5 . 1.5329(15) ?
    C4 H4A . 0.99 ?
    C4 H4B . 0.99 ?
    C5 C6 . 1.4979(14) ?
    C5 H5A . 0.99 ?
    C5 H5B . 0.99 ?
    C6 C7 . 1.4327(13) ?
    C7 C8 . 1.4083(13) ?
    C7 C12 . 1.4150(13) ?
    C8 C9 . 1.3870(14) ?
    C8 H8A . 0.95 ?
    C9 C10 . 1.4096(15) ?
    C10 C11 . 1.3848(15) ?
    C10 H10A . 0.95 ?
    C11 C12 . 1.3964(14) ?
    C11 H11A . 0.95 ?
    C13 H13A . 0.98 ?
    C13 H13B . 0.98 ?
    C13 H13C . 0.98 ?
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 O1 C13 . . 116.68(8) ?
    C1 N1 C12 . . 108.69(8) ?
    C1 N1 H1 . . 124.7(9) ?
    C12 N1 H1 . . 126.4(9) ?
    C6 C1 N1 . . 109.72(9) ?
    C6 C1 C2 . . 125.50(9) ?
    N1 C1 C2 . . 124.73(9) ?
    C1 C2 C3 . . 108.54(9) ?
    C1 C2 H2A . . 110.0 ?
    C3 C2 H2A . . 110.0 ?
    C1 C2 H2B . . 110.0 ?
    C3 C2 H2B . . 110.0 ?
    H2A C2 H2B . . 108.4 ?
    C4 C3 C2 . . 111.42(9) ?
    C4 C3 H3A . . 109.3 ?
    C2 C3 H3A . . 109.3 ?
    C4 C3 H3B . . 109.3 ?
    C2 C3 H3B . . 109.3 ?
    H3A C3 H3B . . 108.0 ?
    C3 C4 C5 . . 112.03(9) ?
    C3 C4 H4A . . 109.2 ?
    C5 C4 H4A . . 109.2 ?
    C3 C4 H4B . . 109.2 ?
    C5 C4 H4B . . 109.2 ?
    H4A C4 H4B . . 107.9 ?
    C6 C5 C4 . . 110.18(9) ?
    C6 C5 H5A . . 109.6 ?
    C4 C5 H5A . . 109.6 ?
    C6 C5 H5B . . 109.6 ?
    C4 C5 H5B . . 109.6 ?
    H5A C5 H5B . . 108.1 ?
    C1 C6 C7 . . 107.08(8) ?
    C1 C6 C5 . . 123.50(9) ?
    C7 C6 C5 . . 129.41(9) ?
    C8 C7 C12 . . 120.09(9) ?
    C8 C7 C6 . . 132.97(9) ?
    C12 C7 C6 . . 106.93(8) ?
    C9 C8 C7 . . 118.14(9) ?
    C9 C8 H8A . . 120.9 ?
    C7 C8 H8A . . 120.9 ?
    O1 C9 C8 . . 124.27(10) ?
    O1 C9 C10 . . 114.63(9) ?
    C8 C9 C10 . . 121.09(9) ?
    C11 C10 C9 . . 121.49(9) ?
    C11 C10 H10A . . 119.3 ?
    C9 C10 H10A . . 119.3 ?
    C10 C11 C12 . . 117.76(10) ?
    C10 C11 H11A . . 121.1 ?
    C12 C11 H11A . . 121.1 ?
    N1 C12 C11 . . 131.00(10) ?
    N1 C12 C7 . . 107.57(9) ?
    C11 C12 C7 . . 121.42(9) ?
    O1 C13 H13A . . 109.5 ?
    O1 C13 H13B . . 109.5 ?
    H13A C13 H13B . . 109.5 ?
    O1 C13 H13C . . 109.5 ?
    H13A C13 H13C . . 109.5 ?
    H13B C13 H13C . . 109.5 ?
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 C6 . . . . -0.59(11) ?
    C12 N1 C1 C2 . . . . 177.03(9) ?
    C6 C1 C2 C3 . . . . 14.48(14) ?
    N1 C1 C2 C3 . . . . -162.77(10) ?
    C1 C2 C3 C4 . . . . -46.60(12) ?
    C2 C3 C4 C5 . . . . 63.94(12) ?
    C3 C4 C5 C6 . . . . -42.77(12) ?
    N1 C1 C6 C7 . . . . 0.80(11) ?
    C2 C1 C6 C7 . . . . -176.80(9) ?
    N1 C1 C6 C5 . . . . -178.39(9) ?
    C2 C1 C6 C5 . . . . 4.01(16) ?
    C4 C5 C6 C1 . . . . 10.21(14) ?
    C4 C5 C6 C7 . . . . -168.79(10) ?
    C1 C6 C7 C8 . . . . -179.49(10) ?
    C5 C6 C7 C8 . . . . -0.36(18) ?
    C1 C6 C7 C12 . . . . -0.71(11) ?
    C5 C6 C7 C12 . . . . 178.41(9) ?
    C12 C7 C8 C9 . . . . 0.33(14) ?
    C6 C7 C8 C9 . . . . 178.98(10) ?
    C13 O1 C9 C8 . . . . 3.57(15) ?
    C13 O1 C9 C10 . . . . -175.98(9) ?
    C7 C8 C9 O1 . . . . -179.13(9) ?
    C7 C8 C9 C10 . . . . 0.40(15) ?
    O1 C9 C10 C11 . . . . 178.46(9) ?
    C8 C9 C10 C11 . . . . -1.11(16) ?
    C9 C10 C11 C12 . . . . 1.03(15) ?
    C1 N1 C12 C11 . . . . 179.80(10) ?
    C1 N1 C12 C7 . . . . 0.13(11) ?
    C10 C11 C12 N1 . . . . -179.93(10) ?
    C10 C11 C12 C7 . . . . -0.29(15) ?
    C8 C7 C12 N1 . . . . 179.32(9) ?
    C6 C7 C12 N1 . . . . 0.36(11) ?
    C8 C7 C12 C11 . . . . -0.39(15) ?
    C6 C7 C12 C11 . . . . -179.36(9) ?
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 <i>Cg</i>1 4_656 0.878(12) 2.409(12) 3.2645(11) 150 y
    C11 H11A <i>Cg</i>2 4_656 0.95 2.6083 3.5018(12) 146 y
