#------------------------------------------------------------------------------
#$Date: 2025-08-19 17:49:58 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301806 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/35/2233578.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_2233578
loop_
_publ_author_name
'Gao, Chao'
'Xiong, Ying'
'Xia, Yong'
'Yu, Luo-Ting'
_publ_section_title
;
 (Morpholin-4-yl)[2-(morpholin-4-yl)-3,5-dinitrophenyl]methanone
;
_journal_coeditor_code           NC2263
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o376
_journal_paper_doi               10.1107/S1600536812000426
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C15 H18 N4 O7'
_chemical_formula_moiety         'C15 H18 N4 O7'
_chemical_formula_sum            'C15 H18 N4 O7'
_chemical_formula_weight         366.33
_chemical_name_systematic
;
(Morpholin-4-yl)[2-(morpholin-4-yl)-3,5-dinitrophenyl]methanone
;
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 108.587(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.2640(4)
_cell_length_b                   21.5488(7)
_cell_length_c                   8.0061(3)
_cell_measurement_reflns_used    2613
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.0374
_cell_measurement_theta_min      2.9774
_cell_volume                     1678.40(11)
_computing_cell_refinement
;
CrysAlis PRO (Oxford Diffraction, 2006)
;
_computing_data_collection
;
CrysAlis PRO (Oxford Diffraction, 2006)
;
_computing_data_reduction
;
CrysAlis PRO (Oxford Diffraction, 2006)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al., 2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al., 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 16.0874
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0174
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7068
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.98
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99376
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Oxford Diffraction, 2006)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.200
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3422
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0683
_refine_ls_R_factor_gt           0.0444
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0426P)²+0.3019P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0958
_refine_ls_wR_factor_ref         0.1095
_reflns_number_gt                2440
_reflns_number_total             3422
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            nc2263.cif
_cod_data_source_block           I
_cod_original_cell_volume        1678.40(10)
_cod_database_code               2233578
_cod_database_fobs_code          2233578
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 '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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
O O1 0.38171(14) 0.03743(7) 0.58276(17) 0.0608(4) Uani d . 1 1
O O2 0.58939(14) 0.11924(7) 0.02632(18) 0.0588(4) Uani d . 1 1
O O3 0.27069(12) 0.25026(6) 0.21720(17) 0.0468(3) Uani d . 1 1
O O4 -0.13992(17) 0.22884(9) -0.4060(2) 0.0884(6) Uani d . 1 1
O O5 -0.30029(15) 0.16911(8) -0.38749(19) 0.0723(5) Uani d . 1 1
O O6 -0.11367(15) 0.07133(8) 0.3247(2) 0.0697(5) Uani d . 1 1
O O7 -0.17948(18) 0.01161(7) 0.0962(2) 0.0825(5) Uani d . 1 1
N N1 -0.18359(16) 0.18932(8) -0.3309(2) 0.0500(4) Uani d . 1 1
N N2 -0.12006(16) 0.05713(8) 0.1748(2) 0.0510(4) Uani d . 1 1
N N3 0.17106(14) 0.09335(6) 0.30645(17) 0.0375(4) Uani d . 1 1
N N4 0.36454(13) 0.17369(6) 0.09991(17) 0.0342(3) Uani d . 1 1
C C1 -0.09372(17) 0.16569(8) -0.1628(2) 0.0361(4) Uani d . 1 1
C C2 -0.14151(17) 0.12014(8) -0.0794(2) 0.0373(4) Uani d . 1 1
H H2 -0.2291 0.1036 -0.1289 0.045 Uiso calc R 1 1
C C3 -0.05571(17) 0.09943(8) 0.0810(2) 0.0342(4) Uani d . 1 1
C C4 0.07972(16) 0.12074(7) 0.1600(2) 0.0307(4) Uani d . 1 1
C C5 0.12146(16) 0.16958(7) 0.0703(2) 0.0306(4) Uani d . 1 1
C C6 0.03563(17) 0.19131(8) -0.0891(2) 0.0357(4) Uani d . 1 1
H H6 0.0648 0.2232 -0.1471 0.043 Uiso calc R 1 1
C C7 0.25205(19) 0.12947(9) 0.4592(2) 0.0464(5) Uani d . 1 1
H H7A 0.2059 0.1302 0.5476 0.056 Uiso calc R 1 1
H H7B 0.2613 0.1719 0.4238 0.056 Uiso calc R 1 1
C C8 0.3922(2) 0.10043(11) 0.5348(3) 0.0563(6) Uani d . 1 1
H H8A 0.4402 0.1024 0.4485 0.068 Uiso calc R 1 1
H H8B 0.4451 0.1236 0.6379 0.068 Uiso calc R 1 1
C C9 0.3045(2) 0.00286(10) 0.4328(3) 0.0570(5) Uani d . 1 1
H H9A 0.2990 -0.0400 0.4668 0.068 Uiso calc R 1 1
H H9B 0.3515 0.0037 0.3452 0.068 Uiso calc R 1 1
C C10 0.16127(19) 0.02827(8) 0.3529(3) 0.0460(5) Uani d . 1 1
H H10A 0.1125 0.0047 0.2485 0.055 Uiso calc R 1 1
H H10B 0.1110 0.0249 0.4366 0.055 Uiso calc R 1 1
C C11 0.25990(16) 0.20097(8) 0.1370(2) 0.0317(4) Uani d . 1 1
C C12 0.49371(17) 0.20777(9) 0.1316(3) 0.0456(5) Uani d . 1 1
H H12A 0.5083 0.2348 0.2329 0.055 Uiso calc R 1 1
H H12B 0.4886 0.2334 0.0301 0.055 Uiso calc R 1 1
C C13 0.61214(19) 0.16320(11) 0.1647(3) 0.0594(6) Uani d . 1 1
H H13A 0.6957 0.1862 0.1754 0.071 Uiso calc R 1 1
H H13B 0.6246 0.1416 0.2749 0.071 Uiso calc R 1 1
C C14 0.4726(2) 0.08302(9) 0.0182(3) 0.0493(5) Uani d . 1 1
H H14A 0.4871 0.0625 0.1305 0.059 Uiso calc R 1 1
H H14B 0.4603 0.0513 -0.0714 0.059 Uiso calc R 1 1
C C15 0.34554(18) 0.12219(8) -0.0241(2) 0.0419(4) Uani d . 1 1
H H15A 0.3240 0.1383 -0.1429 0.050 Uiso calc R 1 1
H H15B 0.2688 0.0968 -0.0189 0.050 Uiso calc R 1 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
C9 O1 C8 109.99(14)
C14 O2 C13 109.29(14)
O4 N1 O5 122.95(17)
O4 N1 C1 118.63(16)
O5 N1 C1 118.41(16)
O6 N2 C3 117.18(17)
O7 N2 O6 124.81(18)
O7 N2 C3 117.97(18)
C4 N3 C7 122.26(14)
C4 N3 C10 122.91(14)
C10 N3 C7 111.36(14)
C11 N4 C12 119.16(14)
C11 N4 C15 122.84(13)
C15 N4 C12 114.60(13)
C2 C1 N1 118.85(15)
C2 C1 C6 121.64(15)
C6 C1 N1 119.47(15)
C1 C2 H2 121.1
C1 C2 C3 117.78(15)
C3 C2 H2 121.1
C2 C3 N2 114.83(15)
C2 C3 C4 123.97(15)
C4 C3 N2 120.94(15)
N3 C4 C3 123.28(15)
N3 C4 C5 121.07(14)
C3 C4 C5 115.44(14)
C4 C5 C11 123.82(14)
C6 C5 C4 120.93(14)
C6 C5 C11 115.25(14)
C1 C6 H6 120.0
C5 C6 C1 120.07(15)
C5 C6 H6 120.0
N3 C7 H7A 109.8
N3 C7 H7B 109.8
N3 C7 C8 109.28(16)
H7A C7 H7B 108.3
C8 C7 H7A 109.8
C8 C7 H7B 109.8
O1 C8 C7 111.10(16)
O1 C8 H8A 109.4
O1 C8 H8B 109.4
C7 C8 H8A 109.4
C7 C8 H8B 109.4
H8A C8 H8B 108.0
O1 C9 H9A 109.2
O1 C9 H9B 109.2
O1 C9 C10 111.99(17)
H9A C9 H9B 107.9
C10 C9 H9A 109.2
C10 C9 H9B 109.2
N3 C10 C9 108.64(15)
N3 C10 H10A 110.0
N3 C10 H10B 110.0
C9 C10 H10A 110.0
C9 C10 H10B 110.0
H10A C10 H10B 108.3
O3 C11 N4 123.45(15)
O3 C11 C5 119.39(15)
N4 C11 C5 117.13(14)
N4 C12 H12A 109.6
N4 C12 H12B 109.6
N4 C12 C13 110.25(16)
H12A C12 H12B 108.1
C13 C12 H12A 109.6
C13 C12 H12B 109.6
O2 C13 C12 111.48(16)
O2 C13 H13A 109.3
O2 C13 H13B 109.3
C12 C13 H13A 109.3
C12 C13 H13B 109.3
H13A C13 H13B 108.0
O2 C14 H14A 109.4
O2 C14 H14B 109.4
O2 C14 C15 111.31(16)
H14A C14 H14B 108.0
C15 C14 H14A 109.4
C15 C14 H14B 109.4
N4 C15 C14 110.89(15)
N4 C15 H15A 109.5
N4 C15 H15B 109.5
C14 C15 H15A 109.5
C14 C15 H15B 109.5
H15A C15 H15B 108.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C8 1.424(2)
O1 C9 1.420(2)
O2 C13 1.419(2)
O2 C14 1.414(2)
O3 C11 1.2275(19)
O4 N1 1.208(2)
O5 N1 1.218(2)
O6 N2 1.220(2)
O7 N2 1.219(2)
N1 C1 1.460(2)
N2 C3 1.465(2)
N3 C4 1.379(2)
N3 C7 1.464(2)
N3 C10 1.463(2)
N4 C11 1.338(2)
N4 C12 1.465(2)
N4 C15 1.460(2)
C1 C2 1.363(2)
C1 C6 1.384(2)
C2 H2 0.9300
C2 C3 1.379(2)
C3 C4 1.408(2)
C4 C5 1.415(2)
C5 C6 1.381(2)
C5 C11 1.509(2)
C6 H6 0.9300
C7 H7A 0.9700
C7 H7B 0.9700
C7 C8 1.507(3)
C8 H8A 0.9700
C8 H8B 0.9700
C9 H9A 0.9700
C9 H9B 0.9700
C9 C10 1.507(2)
C10 H10A 0.9700
C10 H10B 0.9700
C12 H12A 0.9700
C12 H12B 0.9700
C12 C13 1.505(3)
C13 H13A 0.9700
C13 H13B 0.9700
C14 H14A 0.9700
C14 H14B 0.9700
C14 C15 1.499(2)
C15 H15A 0.9700
C15 H15B 0.9700
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
O1 C9 C10 N3 57.5(2)
O2 C14 C15 N4 -54.3(2)
O4 N1 C1 C2 -178.60(18)
O4 N1 C1 C6 3.5(3)
O5 N1 C1 C2 2.8(3)
O5 N1 C1 C6 -175.07(18)
O6 N2 C3 C2 -124.82(18)
O6 N2 C3 C4 49.6(2)
O7 N2 C3 C2 52.9(2)
O7 N2 C3 C4 -132.64(19)
N1 C1 C2 C3 -178.74(15)
N1 C1 C6 C5 179.70(15)
N2 C3 C4 N3 16.1(2)
N2 C3 C4 C5 -169.09(15)
N3 C4 C5 C6 171.26(15)
N3 C4 C5 C11 -8.0(2)
N3 C7 C8 O1 -57.6(2)
N4 C12 C13 O2 54.2(2)
C1 C2 C3 N2 171.64(16)
C1 C2 C3 C4 -2.6(3)
C2 C1 C6 C5 1.9(3)
C2 C3 C4 N3 -170.01(15)
C2 C3 C4 C5 4.8(2)
C3 C4 C5 C6 -3.7(2)
C3 C4 C5 C11 177.09(14)
C4 N3 C7 C8 -144.08(16)
C4 N3 C10 C9 144.78(16)
C4 C5 C6 C1 0.6(2)
C4 C5 C11 O3 -97.7(2)
C4 C5 C11 N4 84.29(19)
C6 C1 C2 C3 -0.9(3)
C6 C5 C11 O3 83.08(19)
C6 C5 C11 N4 -94.98(18)
C7 N3 C4 C3 -131.89(17)
C7 N3 C4 C5 53.6(2)
C7 N3 C10 C9 -55.9(2)
C8 O1 C9 C10 -59.5(2)
C9 O1 C8 C7 59.2(2)
C10 N3 C4 C3 25.3(2)
C10 N3 C4 C5 -149.27(16)
C10 N3 C7 C8 56.40(19)
C11 N4 C12 C13 153.48(16)
C11 N4 C15 C14 -154.09(16)
C11 C5 C6 C1 179.86(15)
C12 N4 C11 O3 -9.5(2)
C12 N4 C11 C5 168.46(14)
C12 N4 C15 C14 47.0(2)
C13 O2 C14 C15 62.6(2)
C14 O2 C13 C12 -62.8(2)
C15 N4 C11 O3 -167.52(16)
C15 N4 C11 C5 10.4(2)
C15 N4 C12 C13 -46.8(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 124023314
