##############################################################################
#                                                                            #
# 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_I
_audit_creation_method     'WinGX routine CIF_UPDATE'
_publ_section_title
;\
Crystal structure of
4,10-dimethoxy-13-methyl-6H,12H-6,12-epiminodibenzo[b,\
f][1,5]dioxocine
;
_publ_section_title_footnote     .
_publ_section_synopsis
;
The Schiff base molecule is transformed into a substituted
dibenzoimino[1,5]dioxocin compound featuring a folded butterfly-like
conformation with a dihedral angle of 84.72 (7)° between the benzene rings.
;
_chemical_name_systematic
;\
4,10-Dimethoxy-13-methyl-6H,12H-6,12-\
epiminodibenzo[b,f][1,5]dioxocine
;
_chemical_formula_moiety     'C17 H17 N O4'
_chemical_formula_sum     'C17 H17 N O4'
_chemical_formula_iupac     'C17 H17 N O4'
_chemical_formula_weight     299.31
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     6.9956(5)
_cell_length_b     8.8589(6)
_cell_length_c     12.0938(9)
_cell_angle_alpha     93.980(6)
_cell_angle_beta     106.603(7)
_cell_angle_gamma     102.133(6)
_cell_volume     695.46(9)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     2735
_cell_measurement_theta_min     3.857
_cell_measurement_theta_max     67.096
_cell_measurement_temperature     100(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     brown
_exptl_crystal_size_max     0.18
_exptl_crystal_size_mid     0.06
_exptl_crystal_size_min     0.04
_exptl_crystal_density_diffrn     1.429
_exptl_crystal_F_000     316
_exptl_absorpt_coefficient_mu     0.842
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2015)
;
_exptl_absorpt_correction_T_min     0.81756
_exptl_absorpt_correction_T_max     1
_diffrn_ambient_temperature     100(2)
_diffrn_radiation_type     CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator     mirror
_diffrn_measurement_device_type     'Oxford Diffraction Gemini'
_diffrn_measurement_device     'four-circle diffractometer'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     10.4738
_diffrn_reflns_number     5235
_diffrn_reflns_av_R_equivalents     0.0266
_diffrn_reflns_theta_min     3.851
_diffrn_reflns_theta_max     67.242
_diffrn_reflns_theta_full     67.243
_diffrn_measured_fraction_theta_max     0.981
_diffrn_measured_fraction_theta_full     0.981
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_l_min     -12
_diffrn_reflns_limit_l_max     14
_reflns_number_total     2456
_reflns_number_gt     2147
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0459
_refine_ls_R_factor_gt     0.0406
_refine_ls_wR_factor_gt     0.1139
_refine_ls_wR_factor_ref     0.1206
_refine_ls_goodness_of_fit_ref     1.065
_refine_ls_restrained_S_all     1.065
_refine_ls_number_reflns     2456
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0737P)²+0.1321P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_refine_ls_shift/su_max     0
_refine_ls_shift/su_mean     0
_refine_diff_density_max     0.222
_refine_diff_density_min     -0.249
_refine_ls_extinction_method     none
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg, 1999) and Mercury (Macrae et al.,
2006)
;
_computing_publication_material
;
WinGX (Farrugia, 1999)
;
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
    C C1 0.8680(3) 0.77719(18) 0.96792(13) 0.0272(4) Uani d 1 . .
    H H1A 1.0173 0.8034 1.0043 0.041 Uiso calc 1 . .
    H H1B 0.802 0.8059 1.0249 0.041 Uiso calc 1 . .
    H H1C 0.8334 0.8345 0.9014 0.041 Uiso calc 1 . .
    N N1 0.7947(2) 0.60859(15) 0.92762(11) 0.0239(3) Uani d 1 . .
    C C11 0.6973(2) 0.64283(16) 0.69544(13) 0.0208(3) Uani d 1 . .
    O O11 0.89314(15) 0.63442(12) 0.75392(9) 0.0216(3) Uani d 1 . .
    C C12 0.5341(2) 0.60187(17) 0.74052(13) 0.0220(3) Uani d 1 . .
    C C121 0.5761(2) 0.56411(17) 0.86455(13) 0.0234(3) Uani d 1 . .
    H H121 0.5042 0.624 0.9056 0.028 Uiso calc 1 . .
    C C13 0.3363(2) 0.60620(17) 0.67238(14) 0.0248(3) Uani d 1 . .
    H H13 0.2232 0.5779 0.7016 0.03 Uiso calc 1 . .
    C C14 0.3059(2) 0.65148(18) 0.56296(14) 0.0260(4) Uani d 1 . .
    H H14 0.1707 0.6494 0.5159 0.031 Uiso calc 1 . .
    C C15 0.4714(2) 0.70032(17) 0.52068(13) 0.0245(3) Uani d 1 . .
    H H15 0.4492 0.7351 0.4465 0.029 Uiso calc 1 . .
    C C16 0.6678(2) 0.69812(17) 0.58676(13) 0.0217(3) Uani d 1 . .
    O O16 0.84270(16) 0.74649(12) 0.55663(9) 0.0252(3) Uani d 1 . .
    C C161 0.8176(3) 0.80636(19) 0.44818(13) 0.0280(4) Uani d 1 . .
    H H16A 0.7297 0.7244 0.3846 0.042 Uiso calc 1 . .
    H H16B 0.9522 0.8411 0.4367 0.042 Uiso calc 1 . .
    H H16C 0.7536 0.8946 0.4488 0.042 Uiso calc 1 . .
    C C21 0.6140(2) 0.31265(18) 0.82770(12) 0.0214(3) Uani d 1 . .
    O O21 0.50055(16) 0.40035(12) 0.86700(9) 0.0242(3) Uani d 1 . .
    C C22 0.8031(2) 0.37774(17) 0.81425(12) 0.0215(3) Uani d 1 . .
    C C221 0.8989(2) 0.55005(17) 0.85422(13) 0.0218(3) Uani d 1 . .
    H H221 1.0459 0.563 0.9011 0.026 Uiso calc 1 . .
    C C23 0.9039(2) 0.28166(18) 0.76738(13) 0.0232(3) Uani d 1 . .
    H H23 1.033 0.3251 0.7573 0.028 Uiso calc 1 . .
    C C24 0.8164(2) 0.12416(18) 0.73579(13) 0.0241(3) Uani d 1 . .
    H H24 0.8838 0.0603 0.7017 0.029 Uiso calc 1 . .
    C C25 0.6289(2) 0.05727(18) 0.75355(13) 0.0235(3) Uani d 1 . .
    H H25 0.5711 -0.0517 0.7332 0.028 Uiso calc 1 . .
    C C26 0.5290(2) 0.15091(18) 0.80075(13) 0.0225(3) Uani d 1 . .
    O O26 0.34536(17) 0.10158(12) 0.82185(10) 0.0275(3) Uani d 1 . .
    C C261 0.2625(3) -0.06296(19) 0.80651(16) 0.0326(4) Uani d 1 . .
    H H26A 0.2318 -0.1056 0.7247 0.049 Uiso calc 1 . .
    H H26B 0.1359 -0.0843 0.8284 0.049 Uiso calc 1 . .
    H H26C 0.3628 -0.1118 0.8559 0.049 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
    C1 N1 . 1.4716(19) ?
    C1 H1A . 0.98 ?
    C1 H1B . 0.98 ?
    C1 H1C . 0.98 ?
    N1 C221 . 1.433(2) ?
    N1 C121 . 1.454(2) ?
    C11 O11 . 1.3707(18) ?
    C11 C12 . 1.394(2) ?
    C11 C16 . 1.410(2) ?
    O11 C221 . 1.4636(17) ?
    C12 C13 . 1.403(2) ?
    C12 C121 . 1.519(2) ?
    C121 O21 . 1.4413(18) ?
    C121 H121 . 1 ?
    C13 C14 . 1.381(2) ?
    C13 H13 . 0.95 ?
    C14 C15 . 1.395(2) ?
    C14 H14 . 0.95 ?
    C15 C16 . 1.382(2) ?
    C15 H15 . 0.95 ?
    C16 O16 . 1.3675(19) ?
    O16 C161 . 1.4271(18) ?
    C161 H16A . 0.98 ?
    C161 H16B . 0.98 ?
    C161 H16C . 0.98 ?
    C21 O21 . 1.3723(18) ?
    C21 C22 . 1.387(2) ?
    C21 C26 . 1.407(2) ?
    C22 C23 . 1.399(2) ?
    C22 C221 . 1.515(2) ?
    C221 H221 . 1 ?
    C23 C24 . 1.379(2) ?
    C23 H23 . 0.95 ?
    C24 C25 . 1.403(2) ?
    C24 H24 . 0.95 ?
    C25 C26 . 1.381(2) ?
    C25 H25 . 0.95 ?
    C26 O26 . 1.3690(19) ?
    O26 C261 . 1.4286(18) ?
    C261 H26A . 0.98 ?
    C261 H26B . 0.98 ?
    C261 H26C . 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
    N1 C1 H1A . . 109.5 ?
    N1 C1 H1B . . 109.5 ?
    H1A C1 H1B . . 109.5 ?
    N1 C1 H1C . . 109.5 ?
    H1A C1 H1C . . 109.5 ?
    H1B C1 H1C . . 109.5 ?
    C221 N1 C121 . . 107.32(12) ?
    C221 N1 C1 . . 114.33(12) ?
    C121 N1 C1 . . 112.09(12) ?
    O11 C11 C12 . . 122.53(13) ?
    O11 C11 C16 . . 116.70(13) ?
    C12 C11 C16 . . 120.76(13) ?
    C11 O11 C221 . . 111.80(11) ?
    C11 C12 C13 . . 118.88(14) ?
    C11 C12 C121 . . 119.41(13) ?
    C13 C12 C121 . . 121.58(13) ?
    O21 C121 N1 . . 108.62(12) ?
    O21 C121 C12 . . 111.51(12) ?
    N1 C121 C12 . . 111.31(12) ?
    O21 C121 H121 . . 108.4 ?
    N1 C121 H121 . . 108.4 ?
    C12 C121 H121 . . 108.4 ?
    C14 C13 C12 . . 120.10(14) ?
    C14 C13 H13 . . 120 ?
    C12 C13 H13 . . 120 ?
    C13 C14 C15 . . 120.80(14) ?
    C13 C14 H14 . . 119.6 ?
    C15 C14 H14 . . 119.6 ?
    C16 C15 C14 . . 119.99(14) ?
    C16 C15 H15 . . 120 ?
    C14 C15 H15 . . 120 ?
    O16 C16 C15 . . 125.65(14) ?
    O16 C16 C11 . . 115.10(13) ?
    C15 C16 C11 . . 119.24(14) ?
    C16 O16 C161 . . 116.22(11) ?
    O16 C161 H16A . . 109.5 ?
    O16 C161 H16B . . 109.5 ?
    H16A C161 H16B . . 109.5 ?
    O16 C161 H16C . . 109.5 ?
    H16A C161 H16C . . 109.5 ?
    H16B C161 H16C . . 109.5 ?
    O21 C21 C22 . . 122.61(14) ?
    O21 C21 C26 . . 116.68(13) ?
    C22 C21 C26 . . 120.72(14) ?
    C21 O21 C121 . . 111.48(11) ?
    C21 C22 C23 . . 119.15(14) ?
    C21 C22 C221 . . 119.33(13) ?
    C23 C22 C221 . . 121.48(13) ?
    N1 C221 O11 . . 111.99(12) ?
    N1 C221 C22 . . 109.13(12) ?
    O11 C221 C22 . . 110.50(11) ?
    N1 C221 H221 . . 108.4 ?
    O11 C221 H221 . . 108.4 ?
    C22 C221 H221 . . 108.4 ?
    C24 C23 C22 . . 120.23(14) ?
    C24 C23 H23 . . 119.9 ?
    C22 C23 H23 . . 119.9 ?
    C23 C24 C25 . . 120.62(14) ?
    C23 C24 H24 . . 119.7 ?
    C25 C24 H24 . . 119.7 ?
    C26 C25 C24 . . 119.59(14) ?
    C26 C25 H25 . . 120.2 ?
    C24 C25 H25 . . 120.2 ?
    O26 C26 C25 . . 125.72(14) ?
    O26 C26 C21 . . 114.69(13) ?
    C25 C26 C21 . . 119.56(14) ?
    C26 O26 C261 . . 116.82(12) ?
    O26 C261 H26A . . 109.5 ?
    O26 C261 H26B . . 109.5 ?
    H26A C261 H26B . . 109.5 ?
    O26 C261 H26C . . 109.5 ?
    H26A C261 H26C . . 109.5 ?
    H26B C261 H26C . . 109.5 ?
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
    C13 H13 O11 1_455 0.95 2.69 3.5616(19) 152.1
    C1 H1B O26 2_667 0.98 2.53 3.508(2) 175.6
data_global
_journal_date_recd_electronic     2017-02-10
_journal_date_accepted     2017-02-11
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2017
_journal_volume     73
_journal_issue      3
_journal_page_first     410
_journal_page_last     412
_journal_paper_category     GO
_journal_paper_doi     10.1107/S2056989017002328
_journal_coeditor_code     HG5482
_publ_contact_author_name     'Vassilyeva, Olga Yu.'
_publ_contact_author_address
;
Department of Chemistry,
Taras Shevchenko National University of Kyiv,
64/13 Volodymyrska Street,
Kyiv 01601, Ukraine
;
_publ_contact_author_email     vassilyeva@univ.kiev.ua
_publ_contact_author_fax     '+380(44)296-2467'
_publ_contact_author_phone     '+380(44)235-4371'
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Kasyanova, Katerina V.' .
;
Department of Chemistry,
Taras Shevchenko National University of Kyiv,
64/13 Volodymyrska Street,
Kyiv 01601, Ukraine
;
    'Kokozay, Vladimir N.' .
;
Department of Chemistry,
Taras Shevchenko National University of Kyiv,
64/13 Volodymyrska Street,
Kyiv 01601, Ukraine
;
    'Buvaylo, Elena A.' .
;
Department of Chemistry,
Taras Shevchenko National University of Kyiv,
64/13 Volodymyrska Street,
Kyiv 01601, Ukraine
;
    'Vassilyeva, Olga Yu.' .
;
Department of Chemistry,
Taras Shevchenko National University of Kyiv,
64/13 Volodymyrska Street,
Kyiv 01601, Ukraine
;
    'Skelton, Brian W.' .
;
School of Molecular Sciences,
M310, University of Western Australia,
Perth, WA 6009,
Australia
;
