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#$Date: 2022-05-09 11:34:02 +0300 (Mon, 09 May 2022) $
#$Revision: 275270 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/51/8105183.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8105183
loop_
_publ_author_name
'Wang, Yin-Xin'
'Qin, Kun'
'Wang, Rui'
'Zhang, Wen-Li'
'Zhong, Qi-Di'
_publ_section_title
;
 Crystal structure of (E)-1-(4-benzyl-3,5-dioxomorpholin-2-ylidene)ethyl
 acetate, C15H15N1O5
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              217
_journal_page_last               218
_journal_paper_doi               10.1515/ncrs-2021-0450
_journal_volume                  237
_journal_year                    2022
_chemical_formula_sum            'C15 H15 N O5'
_chemical_formula_weight         289.28
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                106.064(10)
_cell_angle_beta                 96.091(11)
_cell_angle_gamma                98.189(10)
_cell_formula_units_Z            2
_cell_length_a                   5.075(4)
_cell_length_b                   11.147(8)
_cell_length_c                   13.319(9)
_cell_measurement_reflns_used    1547
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.89
_cell_measurement_theta_min      2.86
_cell_volume                     708.2(9)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXS 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0155
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4176
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.743
_diffrn_reflns_theta_min         1.610
_exptl_absorpt_coefficient_mu    0.103
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_description       block
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2944
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0611
_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
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1403
_refine_ls_wR_factor_ref         0.1581
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2137
_reflns_number_total             2944
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2021-0450_suppl.cif
_cod_data_source_block           202111101_0m
_cod_database_code               8105183
_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. 
;
_shelx_estimated_absorpt_t_min   0.982
_shelx_estimated_absorpt_t_max   0.985
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2758(2) 0.25763(11) 0.77312(9) 0.0491(3) Uani 1 1 d . . . . .
O2 O 0.5557(3) 0.19720(14) 0.88394(11) 0.0645(4) Uani 1 1 d . . . . .
O3 O 0.7462(3) 0.22041(11) 0.58637(9) 0.0540(4) Uani 1 1 d . . . . .
O4 O 0.6944(3) 0.45584(11) 0.82403(10) 0.0601(4) Uani 1 1 d . . . . .
O5 O 1.2367(3) 0.47210(14) 0.57681(12) 0.0702(4) Uani 1 1 d . . . . .
N1 N 0.9774(3) 0.46502(13) 0.70509(11) 0.0457(4) Uani 1 1 d . . . . .
C1 C 1.1582(4) 0.81208(19) 0.85985(15) 0.0645(5) Uani 1 1 d . . . . .
H1 H 1.300609 0.810195 0.909143 0.077 Uiso 1 1 calc R U . . .
C2 C 1.0682(5) 0.92528(19) 0.86500(18) 0.0753(7) Uani 1 1 d . . . . .
H2 H 1.150879 0.998838 0.917953 0.090 Uiso 1 1 calc R U . . .
C3 C 0.8590(5) 0.9298(2) 0.7929(2) 0.0744(7) Uani 1 1 d . . . . .
H3 H 0.798946 1.005732 0.796849 0.089 Uiso 1 1 calc R U . . .
C4 C 0.7394(4) 0.8211(2) 0.7151(2) 0.0726(6) Uani 1 1 d . . . . .
H4 H 0.598107 0.823635 0.665680 0.087 Uiso 1 1 calc R U . . .
C5 C 0.8259(4) 0.70769(17) 0.70910(15) 0.0527(5) Uani 1 1 d . . . . .
H5 H 0.741517 0.634717 0.655869 0.063 Uiso 1 1 calc R U . . .
C6 C 1.0355(3) 0.70137(15) 0.78093(12) 0.0426(4) Uani 1 1 d . . . . .
C7 C 1.1414(3) 0.58140(16) 0.77989(15) 0.0527(5) Uani 1 1 d . . . . .
H7A H 1.322547 0.589932 0.762390 0.063 Uiso 1 1 calc R U . . .
H7B H 1.152946 0.572299 0.850493 0.063 Uiso 1 1 calc R U . . .
C8 C 1.0428(4) 0.42022(17) 0.60509(15) 0.0517(4) Uani 1 1 d . . . . .
C9 C 0.8524(5) 0.30636(19) 0.53250(15) 0.0616(5) Uani 1 1 d . . . . .
H9A H 0.704602 0.334445 0.498345 0.074 Uiso 1 1 calc R U . . .
H9B H 0.946114 0.262111 0.477833 0.074 Uiso 1 1 calc R U . . .
C10 C 0.6245(3) 0.27695(15) 0.67069(12) 0.0429(4) Uani 1 1 d . . . . .
C11 C 0.7589(3) 0.40466(15) 0.73986(13) 0.0437(4) Uani 1 1 d . . . . .
C12 C 0.4084(3) 0.20737(16) 0.68940(13) 0.0445(4) Uani 1 1 d . . . . .
C13 C 0.2845(4) 0.07532(18) 0.62471(17) 0.0638(5) Uani 1 1 d . . . . .
H13A H 0.363514 0.053300 0.561203 0.096 Uiso 1 1 calc R U . . .
H13B H 0.094045 0.070013 0.606696 0.096 Uiso 1 1 calc R U . . .
H13C H 0.316132 0.017634 0.664583 0.096 Uiso 1 1 calc R U . . .
C14 C 0.3741(3) 0.25106(16) 0.87100(13) 0.0460(4) Uani 1 1 d . . . . .
C15 C 0.2252(4) 0.3173(2) 0.95281(16) 0.0663(6) Uani 1 1 d . . . . .
H15A H 0.285295 0.304005 1.019070 0.099 Uiso 1 1 calc R U . . .
H15B H 0.035783 0.284220 0.932244 0.099 Uiso 1 1 calc R U . . .
H15C H 0.257792 0.406457 0.960155 0.099 Uiso 1 1 calc R U . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C14 O1 C12 117.66(13) . .
C10 O3 C9 113.40(14) . .
C8 N1 C11 122.96(15) . .
C8 N1 C7 119.51(15) . .
C11 N1 C7 117.53(14) . .
C2 C1 C6 120.1(2) . .
C2 C1 H1 120.0 . .
C6 C1 H1 120.0 . .
C3 C2 C1 120.72(19) . .
C3 C2 H2 119.6 . .
C1 C2 H2 119.6 . .
C4 C3 C2 119.2(2) . .
C4 C3 H3 120.4 . .
C2 C3 H3 120.4 . .
C3 C4 C5 120.9(2) . .
C3 C4 H4 119.6 . .
C5 C4 H4 119.6 . .
C6 C5 C4 120.78(17) . .
C6 C5 H5 119.6 . .
C4 C5 H5 119.6 . .
C5 C6 C1 118.42(17) . .
C5 C6 C7 124.03(14) . .
C1 C6 C7 117.55(17) . .
N1 C7 C6 114.58(15) . .
N1 C7 H7A 108.6 . .
C6 C7 H7A 108.6 . .
N1 C7 H7B 108.6 . .
C6 C7 H7B 108.6 . .
H7A C7 H7B 107.6 . .
O5 C8 N1 122.20(18) . .
O5 C8 C9 122.38(18) . .
N1 C8 C9 115.37(15) . .
O3 C9 C8 112.72(17) . .
O3 C9 H9A 109.0 . .
C8 C9 H9A 109.0 . .
O3 C9 H9B 109.0 . .
C8 C9 H9B 109.0 . .
H9A C9 H9B 107.8 . .
C12 C10 O3 117.17(15) . .
C12 C10 C11 124.89(15) . .
O3 C10 C11 117.62(14) . .
O4 C11 N1 119.67(15) . .
O4 C11 C10 123.66(15) . .
N1 C11 C10 116.64(14) . .
C10 C12 O1 120.47(15) . .
C10 C12 C13 125.21(15) . .
O1 C12 C13 114.30(15) . .
C12 C13 H13A 109.5 . .
C12 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
C12 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
O2 C14 O1 121.94(16) . .
O2 C14 C15 126.93(18) . .
O1 C14 C15 111.13(16) . .
C14 C15 H15A 109.5 . .
C14 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
C14 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C14 1.371(2) .
O1 C12 1.3895(19) .
O2 C14 1.192(2) .
O3 C10 1.3808(19) .
O3 C9 1.428(2) .
O4 C11 1.211(2) .
O5 C8 1.217(2) .
N1 C8 1.381(2) .
N1 C11 1.402(2) .
N1 C7 1.473(2) .
C1 C2 1.389(3) .
C1 C6 1.393(2) .
C1 H1 0.9300 .
C2 C3 1.370(3) .
C2 H2 0.9300 .
C3 C4 1.368(3) .
C3 H3 0.9300 .
C4 C5 1.381(3) .
C4 H4 0.9300 .
C5 C6 1.376(3) .
C5 H5 0.9300 .
C6 C7 1.508(3) .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C8 C9 1.501(3) .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C10 C12 1.337(2) .
C10 C11 1.485(2) .
C12 C13 1.491(3) .
C13 H13A 0.9600 .
C13 H13B 0.9600 .
C13 H13C 0.9600 .
C14 C15 1.480(3) .
C15 H15A 0.9600 .
C15 H15B 0.9600 .
C15 H15C 0.9600 .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C6 C1 C2 C3 -0.1(3) . . . .
C1 C2 C3 C4 -0.2(3) . . . .
C2 C3 C4 C5 0.4(3) . . . .
C3 C4 C5 C6 -0.3(3) . . . .
C4 C5 C6 C1 0.0(3) . . . .
C4 C5 C6 C7 179.90(18) . . . .
C2 C1 C6 C5 0.2(3) . . . .
C2 C1 C6 C7 -179.70(18) . . . .
C8 N1 C7 C6 94.23(18) . . . .
C11 N1 C7 C6 -85.68(19) . . . .
C5 C6 C7 N1 -8.8(2) . . . .
C1 C6 C7 N1 171.13(15) . . . .
C11 N1 C8 O5 -178.35(16) . . . .
C7 N1 C8 O5 1.7(3) . . . .
C11 N1 C8 C9 4.0(2) . . . .
C7 N1 C8 C9 -175.95(16) . . . .
C10 O3 C9 C8 54.6(2) . . . .
O5 C8 C9 O3 146.41(19) . . . .
N1 C8 C9 O3 -35.9(2) . . . .
C9 O3 C10 C12 144.87(17) . . . .
C9 O3 C10 C11 -41.3(2) . . . .
C8 N1 C11 O4 -172.02(16) . . . .
C7 N1 C11 O4 7.9(2) . . . .
C8 N1 C11 C10 10.0(2) . . . .
C7 N1 C11 C10 -170.09(14) . . . .
C12 C10 C11 O4 4.4(3) . . . .
O3 C10 C11 O4 -168.97(16) . . . .
C12 C10 C11 N1 -177.72(15) . . . .
O3 C10 C11 N1 8.9(2) . . . .
O3 C10 C12 O1 179.75(13) . . . .
C11 C10 C12 O1 6.4(3) . . . .
O3 C10 C12 C13 -1.8(3) . . . .
C11 C10 C12 C13 -175.23(17) . . . .
C14 O1 C12 C10 -84.7(2) . . . .
C14 O1 C12 C13 96.77(19) . . . .
C12 O1 C14 O2 -4.8(2) . . . .
C12 O1 C14 C15 175.53(15) . . . .
