##############################################################################
#                                                                            #
# 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     'from SHELXL97 CIF and IUCr SHELXL97-template'
_journal_date_recd_electronic     2016-11-23
_journal_date_accepted     2016-12-25
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2017
_journal_volume     73
_journal_issue      2
_journal_page_first     118
_journal_page_last     121
_journal_paper_category     GO
_journal_paper_doi     10.1107/S2056989016020508
_journal_coeditor_code     XU5896
_publ_contact_author_name     'Van Tuyen Nguyen'
_publ_contact_author_address
;
Institute of Chemistry, Vietnam Academy of Science and Technology,
18 Hoang Quoc Viet, Hanoi, Vietnam
;
_publ_contact_author_email     'ngvtuyen@hotmail.com'
_publ_contact_author_fax     '+844-37-54-74-29'
_publ_contact_author_phone     '+844-37-54-70-15'
_publ_section_title
;\
Crystal structure of
22,24,25-trimethyl-8,11,14-trioxa-25-azatetracyclo[19.3.1.0^2,7^.0^15,20^]\
pentacosa-2,4,6,15(20),16,18-hexaen-23-one
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Nguyen, Van Tuyen' .
;
Institute of Chemistry, Vietnam Academy of Science and Technology,
18 Hoang Quoc Viet, Hanoi,
Vietnam
Graduate University of Science and Technplogy, 18 Hoang Quoc Viet, Hanoi,
Vietnam
;
    'Truong, Hong Hieu' .
;
Department of Biotechnology, Vietnam--Russia Tropical Centre,
58 Nguyen Van Huyen, Hanoi,
Vietnam
;
    'Le, Tuan Anh' .
;
Faculty of Chemistry, VNU University of Science, Vietnam National University,
19 Le Thanh Tong, Hoan Kiem, Hanoi,
Vietnam
;
    'Soldatenkov, Anatoly T.' .
;
Organic Chemistry Department, Peoples' Friendship University of Russia,
6 Miklukho-Maklaya St., Moscow 117198, Russian Federation
;
    'Thi, Tuyet Anh Dang' .
;
Institute of Chemistry, Vietnam Academy of Science and Technology,
18 Hoang Quoc Viet, Hanoi,
Vietnam
;
    'Tran, Thi Thanh Van' .
;
Faculty of Chemistry, VNU University of Science, Vietnam National University,
19 Le Thanh Tong, Hoan Kiem, Hanoi,
Vietnam
;
    'Esina, Natalia Ya.' .
;
Inorganic Chemistry Department, Peoples' Friendship University of Russia,
6 Miklukho-Maklay St., Moscow 117198, Russian Federation
;
    'Khrustalev, Victor N.' .
;
Inorganic Chemistry Department, Peoples' Friendship University of Russia,
6 Miklukho-Maklay St., Moscow 117198, Russian Federation
X-Ray Structural Centre,
A.N. Nesmeyanov Institute of Organoelement Compounds,
Russian Academy of Sciences,
28 Vavilov St., B-334, Moscow 119991, Russian Federation
;
_publ_section_synopsis
;\
Macrocyclic
22,24,25-trimethyl-8,11,14-trioxa-25-azatetracyclo[19.3.1.0^2,7^.0^15,20^]\
pentacosa-2,4,6,15(20),16,18-hexaen-23-one obtained by a Petrenko--Kritchenko
condensation of 1,5-bis(2-formylphenoxy)-3-oxapentane, pentan-3-one and
methylammonium acetate has been studied by X-ray structural analysis.
;
data_I
_audit_creation_method     'SHELXTL (Sheldrick, 2015)'
_chemical_name_systematic
;\
22,24,25-Trimethyl-8,11,14-trioxa-25-azatetracyclo[19.3.1.0^2,7^.0^15,20^]\
pentacosa-2,4,6,15(20),16,18-hexaen-23-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C24 H29 N O4'
_chemical_formula_sum     'C24 H29 N O4'
_chemical_formula_iupac     'C24 H29 N O4'
_chemical_formula_weight     395.48
_chemical_melting_point     ?
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system     orthorhombic
_space_group_name_H-M_alt     'P n m a'
_space_group_name_Hall     '-P 2ac 2n'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    '-x, y+1/2, -z'
    'x+1/2, -y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, y, -z-1/2'
    'x, -y-1/2, z'
    '-x-1/2, y-1/2, z-1/2'
_cell_length_a     8.1468(5)
_cell_length_b     20.3402(11)
_cell_length_c     12.0155(7)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     1991.1(2)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     4090
_cell_measurement_theta_min     3.02
_cell_measurement_theta_max     29.19
_cell_measurement_temperature     120(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.20
_exptl_crystal_size_mid     0.15
_exptl_crystal_size_min     0.15
_exptl_crystal_density_diffrn     1.319
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     848
_exptl_absorpt_coefficient_mu     0.089
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2003)
;
_shelx_estimated_absorpt_T_min     0.982
_shelx_estimated_absorpt_T_max     0.987
_exptl_absorpt_correction_T_min     0.970
_exptl_absorpt_correction_T_max     0.980
_diffrn_ambient_temperature     120(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type     'Bruker APEXII CCD'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     25079
_diffrn_reflns_av_R_equivalents     0.0653
_diffrn_reflns_theta_min     1.969
_diffrn_reflns_theta_max     30.562
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -29
_diffrn_reflns_limit_k_max     29
_diffrn_reflns_limit_l_min     -17
_diffrn_reflns_limit_l_max     16
_refine_special_details     ?
_reflns_number_total     3128
_reflns_number_gt     2469
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0760
_refine_ls_R_factor_gt     0.0561
_refine_ls_wR_factor_gt     0.1197
_refine_ls_wR_factor_ref     0.1298
_refine_ls_goodness_of_fit_ref     1.018
_refine_ls_restrained_S_all     1.018
_refine_ls_number_reflns     3128
_refine_ls_number_parameters     140
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                 'w=1/[σ²(Fo²)+(0.046P)²+1.66P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.340
_refine_diff_density_min     -0.234
_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, 2005)
;
_computing_cell_refinement
;
SAINT (Bruker, 2001)
;
_computing_data_reduction
;
SAINT (Bruker, 2001)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL2015 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
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 0.58338(18) 0.30912(7) -0.07447(12) 0.0151(3) Uani d 1 . .
    H H1 0.4639 0.3029 -0.0903 0.018 Uiso calc 1 . .
    C C2 0.60218(18) 0.37109(7) -0.00494(12) 0.0156(3) Uani d 1 . .
    C C3 0.75023(19) 0.40480(7) 0.00526(13) 0.0190(3) Uani d 1 . .
    H H3 0.8432 0.3900 -0.0354 0.023 Uiso calc 1 . .
    C C4 0.7652(2) 0.45976(7) 0.07366(14) 0.0223(3) Uani d 1 . .
    H H4 0.8670 0.4822 0.0793 0.027 Uiso calc 1 . .
    C C5 0.6301(2) 0.48134(7) 0.13342(13) 0.0223(3) Uani d 1 . .
    H H5 0.6398 0.5188 0.1803 0.027 Uiso calc 1 . .
    C C6 0.4808(2) 0.44885(7) 0.12557(13) 0.0195(3) Uani d 1 . .
    H H6 0.3888 0.4637 0.1672 0.023 Uiso calc 1 . .
    C C7 0.46690(18) 0.39412(7) 0.05590(12) 0.0162(3) Uani d 1 . .
    O O8 0.32384(13) 0.35995(5) 0.04244(9) 0.0194(2) Uani d 1 . .
    C C9 0.19912(19) 0.36553(8) 0.12588(13) 0.0201(3) Uani d 1 . .
    H H9A 0.1387 0.4074 0.1172 0.024 Uiso calc 1 . .
    H H9B 0.2488 0.3645 0.2011 0.024 Uiso calc 1 . .
    C C10 0.08483(19) 0.30816(7) 0.11056(13) 0.0197(3) Uani d 1 . .
    H H10A -0.0119 0.3129 0.1597 0.024 Uiso calc 1 . .
    H H10B 0.0462 0.3062 0.0325 0.024 Uiso calc 1 . .
    O O11 0.17272(19) 0.2500 0.13785(13) 0.0192(3) Uani d 1 . .
    C C12 0.6367(3) 0.2500 -0.24937(18) 0.0157(4) Uani d 1 . .
    O O12 0.5743(2) 0.2500 -0.34102(13) 0.0219(3) Uani d 1 . .
    C C13 0.67442(18) 0.31314(7) -0.18726(12) 0.0160(3) Uani d 1 . .
    H H13 0.7951 0.3147 -0.1722 0.019 Uiso calc 1 . .
    N N14 0.6428(2) 0.2500 -0.01435(14) 0.0148(3) Uani d 1 . .
    C C15 0.6282(2) 0.37347(7) -0.25565(13) 0.0192(3) Uani d 1 . .
    H H15A 0.6833 0.3715 -0.3281 0.029 Uiso calc 1 . .
    H H15B 0.6626 0.4133 -0.2161 0.029 Uiso calc 1 . .
    H H15C 0.5091 0.3744 -0.2667 0.029 Uiso calc 1 . .
    C C16 0.6033(3) 0.2500 0.10474(17) 0.0186(4) Uani d 1 . .
    H H16A 0.6489 0.2885 0.1390 0.028 Uiso d 1 . .
    H H16B 0.4864 0.2500 0.1141 0.028 Uiso d 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 N14 . 1.4840(17) ?
    C1 C2 . 1.5197(19) ?
    C1 C13 . 1.547(2) ?
    C1 H1 . 1.0000 ?
    C2 C3 . 1.393(2) ?
    C2 C7 . 1.403(2) ?
    C3 C4 . 1.393(2) ?
    C3 H3 . 0.9500 ?
    C4 C5 . 1.385(2) ?
    C4 H4 . 0.9500 ?
    C5 C6 . 1.388(2) ?
    C5 H5 . 0.9500 ?
    C6 C7 . 1.397(2) ?
    C6 H6 . 0.9500 ?
    C7 O8 . 1.3666(18) ?
    O8 C9 . 1.4319(18) ?
    C9 C10 . 1.504(2) ?
    C9 H9A . 0.9900 ?
    C9 H9B . 0.9900 ?
    C10 O11 . 1.4211(17) ?
    C10 H10A . 0.9900 ?
    C10 H10B . 0.9900 ?
    O11 C10 7_565 1.4211(17) ?
    C12 O12 . 1.213(3) ?
    C12 C13 7_565 1.5168(18) ?
    C12 C13 . 1.5168(18) ?
    C13 C15 . 1.524(2) ?
    C13 H13 . 1.0000 ?
    N14 C16 . 1.467(3) ?
    N14 C1 7_565 1.4840(17) ?
    C15 H15A . 0.9800 ?
    C15 H15B . 0.9800 ?
    C15 H15C . 0.9800 ?
    C16 H16A . 0.9595 ?
    C16 H16B . 0.9593 ?
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
    N14 C1 C2 . . 111.82(12) ?
    N14 C1 C13 . . 108.23(12) ?
    C2 C1 C13 . . 112.92(12) ?
    N14 C1 H1 . . 107.9 ?
    C2 C1 H1 . . 107.9 ?
    C13 C1 H1 . . 107.9 ?
    C3 C2 C7 . . 118.03(13) ?
    C3 C2 C1 . . 122.95(13) ?
    C7 C2 C1 . . 118.96(13) ?
    C2 C3 C4 . . 121.51(15) ?
    C2 C3 H3 . . 119.2 ?
    C4 C3 H3 . . 119.2 ?
    C5 C4 C3 . . 119.40(15) ?
    C5 C4 H4 . . 120.3 ?
    C3 C4 H4 . . 120.3 ?
    C4 C5 C6 . . 120.68(14) ?
    C4 C5 H5 . . 119.7 ?
    C6 C5 H5 . . 119.7 ?
    C5 C6 C7 . . 119.40(14) ?
    C5 C6 H6 . . 120.3 ?
    C7 C6 H6 . . 120.3 ?
    O8 C7 C6 . . 123.03(14) ?
    O8 C7 C2 . . 116.00(12) ?
    C6 C7 C2 . . 120.97(14) ?
    C7 O8 C9 . . 118.82(11) ?
    O8 C9 C10 . . 106.99(12) ?
    O8 C9 H9A . . 110.3 ?
    C10 C9 H9A . . 110.3 ?
    O8 C9 H9B . . 110.3 ?
    C10 C9 H9B . . 110.3 ?
    H9A C9 H9B . . 108.6 ?
    O11 C10 C9 . . 107.80(13) ?
    O11 C10 H10A . . 110.1 ?
    C9 C10 H10A . . 110.1 ?
    O11 C10 H10B . . 110.1 ?
    C9 C10 H10B . . 110.1 ?
    H10A C10 H10B . . 108.5 ?
    C10 O11 C10 . 7_565 112.69(16) ?
    O12 C12 C13 . 7_565 122.11(9) ?
    O12 C12 C13 . . 122.11(9) ?
    C13 C12 C13 7_565 . 115.71(18) ?
    C12 C13 C15 . . 111.50(13) ?
    C12 C13 C1 . . 106.80(12) ?
    C15 C13 C1 . . 113.36(12) ?
    C12 C13 H13 . . 108.3 ?
    C15 C13 H13 . . 108.3 ?
    C1 C13 H13 . . 108.3 ?
    C16 N14 C1 . 7_565 113.80(10) ?
    C16 N14 C1 . . 113.80(10) ?
    C1 N14 C1 7_565 . 108.27(15) ?
    C13 C15 H15A . . 109.5 ?
    C13 C15 H15B . . 109.5 ?
    H15A C15 H15B . . 109.5 ?
    C13 C15 H15C . . 109.5 ?
    H15A C15 H15C . . 109.5 ?
    H15B C15 H15C . . 109.5 ?
    N14 C16 H16A . . 109.5 ?
    N14 C16 H16B . . 109.4 ?
    H16A C16 H16B . . 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
    N14 C1 C2 C3 . . . . 80.51(18) ?
    C13 C1 C2 C3 . . . . -41.84(19) ?
    N14 C1 C2 C7 . . . . -96.59(16) ?
    C13 C1 C2 C7 . . . . 141.06(13) ?
    C7 C2 C3 C4 . . . . 0.1(2) ?
    C1 C2 C3 C4 . . . . -177.05(14) ?
    C2 C3 C4 C5 . . . . 0.3(2) ?
    C3 C4 C5 C6 . . . . -0.1(2) ?
    C4 C5 C6 C7 . . . . -0.5(2) ?
    C5 C6 C7 O8 . . . . -179.15(14) ?
    C5 C6 C7 C2 . . . . 0.9(2) ?
    C3 C2 C7 O8 . . . . 179.34(13) ?
    C1 C2 C7 O8 . . . . -3.41(19) ?
    C3 C2 C7 C6 . . . . -0.7(2) ?
    C1 C2 C7 C6 . . . . 176.59(13) ?
    C6 C7 O8 C9 . . . . -20.6(2) ?
    C2 C7 O8 C9 . . . . 159.44(13) ?
    C7 O8 C9 C10 . . . . -161.82(12) ?
    O8 C9 C10 O11 . . . . 67.31(16) ?
    C9 C10 O11 C10 . . . 7_565 -171.15(10) ?
    O12 C12 C13 C15 . . . . -1.4(2) ?
    C13 C12 C13 C15 7_565 . . . -178.58(11) ?
    O12 C12 C13 C1 . . . . 122.9(2) ?
    C13 C12 C13 C1 7_565 . . . -54.2(2) ?
    N14 C1 C13 C12 . . . . 58.80(16) ?
    C2 C1 C13 C12 . . . . -176.87(13) ?
    N14 C1 C13 C15 . . . . -178.02(12) ?
    C2 C1 C13 C15 . . . . -53.68(16) ?
    C2 C1 N14 C16 . . . . 38.57(19) ?
    C13 C1 N14 C16 . . . . 163.56(14) ?
    C2 C1 N14 C1 . . . 7_565 166.15(9) ?
    C13 C1 N14 C1 . . . 7_565 -68.85(18) ?
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
    C10 H10B O12 4_454 0.99 2.58 3.449(2) 147
    C16 H16B O11 . 0.96 2.57 3.530(3) 180
_shelxl_version_number     2014/6
