#------------------------------------------------------------------------------
#$Date: 2025-04-22 19:48:50 +0300 (Tue, 22 Apr 2025) $
#$Revision: 299347 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/55/8105551.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_8105551
loop_
_publ_author_name
'Chen, Xiao-Ming'
'Zhang, Xing-Yu'
'He, Fu-Lin'
'Pan, Jun'
'Jia, Guo-Kai'
_publ_section_title
;
 Crystal structure of (2E,4Z)-dimethyl
 4-((phenylamino)methylene)pent-2-enedioate, C14H15N1O4
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              87
_journal_page_last               89
_journal_paper_doi               10.1515/ncrs-2018-0194
_journal_volume                  234
_journal_year                    2018
_chemical_formula_moiety         'C14 H15 N O4'
_chemical_formula_sum            'C14 H15 N O4'
_chemical_formula_weight         261.27
_chemical_name_systematic
;
(2E,4Z)-dimethyl 4-((phenylamino)methylene)pent-2-enedioate
;
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                79.242(2)
_cell_angle_beta                 78.647(3)
_cell_angle_gamma                85.496(3)
_cell_formula_units_Z            4
_cell_length_a                   8.2018(4)
_cell_length_b                   11.5512(5)
_cell_length_c                   14.4121(7)
_cell_measurement_reflns_used    7358
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.44
_cell_measurement_theta_min      2.51
_cell_volume                     1313.93(11)
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans '
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0169
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            20977
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.586
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6889
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
ADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0740 before and 0.0338 after correction.
The Ratio of minimum to maximum transmission is 0.9241.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details ' '
_refine_ls_abs_structure_Flack   ' '
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     347
_refine_ls_number_reflns         5899
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0548
_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)+(0.1052P)²+0.1148P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1565
_refine_ls_wR_factor_ref         0.1805
_cod_data_source_file            suppl_ncrs-2018-0194_suppl.cif
_cod_data_source_block           1
_cod_depositor_comments
;

2025-04-22
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_weight         522.54
_cod_original_formula_moiety         '2(C14 H15 N O4)'
_cod_original_formula_units_Z            2
_cod_original_sg_symbol_H-M      'P -1 '
_cod_original_formula_sum        'C28 H30 N2 O8 '
_cod_database_code               8105551
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 'x, y, z'
2 '-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
O7 O 0.82537(15) 0.62219(10) 0.75870(8) 0.0605(3) Uani 1 1 d . . . . .
O3 O 0.83969(15) 0.43118(10) 0.46707(9) 0.0607(3) Uani 1 1 d . . . . .
O4 O 0.71137(16) 0.42066(10) 0.61983(9) 0.0638(3) Uani 1 1 d . . . . .
O5 O 0.80262(16) 0.91956(10) 0.50978(8) 0.0632(4) Uani 1 1 d . . . . .
O6 O 0.64784(17) 1.08640(10) 0.51680(8) 0.0691(4) Uani 1 1 d . . . . .
O1 O 0.77740(18) 0.70625(10) 0.20914(8) 0.0703(4) Uani 1 1 d . . . . .
O8 O 0.71188(16) 0.61463(11) 0.91433(9) 0.0684(4) Uani 1 1 d . . . . .
O2 O 0.68179(19) 0.89080(10) 0.21902(9) 0.0745(4) Uani 1 1 d . . . . .
N1 N 0.49067(16) 0.59313(10) 0.66189(9) 0.0503(3) Uani 1 1 d . . . . .
H1 H 0.539924 0.527202 0.681547 0.060 Uiso 1 1 calc R . . . .
N2 N 0.49905(17) 0.79047(11) 0.95934(9) 0.0540(4) Uani 1 1 d . . . . .
H2 H 0.546581 0.723685 0.978604 0.065 Uiso 1 1 calc R . . . .
C18 C 0.69641(19) 0.84022(12) 0.70105(10) 0.0451(3) Uani 1 1 d . . . . .
H18 H 0.775211 0.799546 0.661877 0.054 Uiso 1 1 calc R . . . .
C8 C 0.53875(19) 0.63916(12) 0.56918(11) 0.0457(4) Uani 1 1 d . . . . .
H8 H 0.490213 0.711800 0.546611 0.055 Uiso 1 1 calc R . . . .
C6 C 0.73413(19) 0.47397(13) 0.53767(11) 0.0481(4) Uani 1 1 d . . . . .
C5 C 0.65401(19) 0.58790(12) 0.50454(11) 0.0452(4) Uani 1 1 d . . . . .
C22 C 0.54497(19) 0.83624(13) 0.86660(10) 0.0476(4) Uani 1 1 d . . . . .
H22 H 0.498156 0.909819 0.844825 0.057 Uiso 1 1 calc R . . . .
C19 C 0.65539(19) 0.78393(13) 0.80070(11) 0.0463(4) Uani 1 1 d . . . . .
C20 C 0.7313(2) 0.66769(13) 0.83123(11) 0.0495(4) Uani 1 1 d . . . . .
C9 C 0.3710(2) 0.63771(13) 0.73128(11) 0.0469(4) Uani 1 1 d . . . . .
C4 C 0.69484(19) 0.64128(12) 0.40386(11) 0.0475(4) Uani 1 1 d . . . . .
H4 H 0.763220 0.595024 0.364360 0.057 Uiso 1 1 calc R . . . .
C16 C 0.6924(2) 0.99066(13) 0.55655(11) 0.0484(4) Uani 1 1 d . . . . .
C23 C 0.3829(2) 0.83753(13) 1.02953(11) 0.0486(4) Uani 1 1 d . . . . .
C2 C 0.7012(2) 0.79044(14) 0.25783(11) 0.0525(4) Uani 1 1 d . . . . .
C17 C 0.6367(2) 0.94246(13) 0.65769(11) 0.0524(4) Uani 1 1 d . . . . .
H17 H 0.555412 0.985021 0.693859 0.063 Uiso 1 1 calc R . . . .
C28 C 0.2854(2) 0.93922(15) 1.00824(12) 0.0610(5) Uani 1 1 d . . . . .
H28 H 0.294166 0.979222 0.945284 0.073 Uiso 1 1 calc R . . . .
C10 C 0.3468(2) 0.57444(15) 0.82455(12) 0.0585(4) Uani 1 1 d . . . . .
H10 H 0.407962 0.504172 0.838282 0.070 Uiso 1 1 calc R . . . .
C14 C 0.2781(2) 0.74213(15) 0.71127(12) 0.0589(4) Uani 1 1 d . . . . .
H14 H 0.291918 0.785525 0.649245 0.071 Uiso 1 1 calc R . . . .
C24 C 0.3650(3) 0.77924(16) 1.12374(13) 0.0654(5) Uani 1 1 d . . . . .
H24 H 0.428938 0.710530 1.138385 0.078 Uiso 1 1 calc R . . . .
C3 C 0.6484(2) 0.74683(14) 0.36010(11) 0.0556(4) Uani 1 1 d . . . . .
H3 H 0.578455 0.795488 0.396742 0.067 Uiso 1 1 calc R . . . .
C11 C 0.2339(3) 0.61424(16) 0.89659(12) 0.0671(5) Uani 1 1 d . . . . .
H11 H 0.219312 0.571263 0.958773 0.080 Uiso 1 1 calc R . . . .
C13 C 0.1650(3) 0.78041(17) 0.78491(13) 0.0709(5) Uani 1 1 d . . . . .
H13 H 0.102876 0.850376 0.771701 0.085 Uiso 1 1 calc R . . . .
C27 C 0.1756(3) 0.98000(16) 1.08157(13) 0.0704(5) Uani 1 1 d . . . . .
H27 H 0.110535 1.048271 1.067512 0.085 Uiso 1 1 calc R . . . .
C15 C 0.8677(3) 0.96535(17) 0.41106(12) 0.0709(5) Uani 1 1 d . . . . .
H15A H 0.777904 0.983005 0.376127 0.106 Uiso 1 1 calc GR . . . .
H15B H 0.943798 0.907734 0.383888 0.106 Uiso 1 1 calc GR . . . .
H15C H 0.925005 1.035972 0.407032 0.106 Uiso 1 1 calc GR . . . .
C12 C 0.1417(3) 0.71829(18) 0.87677(13) 0.0714(5) Uani 1 1 d . . . . .
H12 H 0.064800 0.745704 0.925300 0.086 Uiso 1 1 calc R . . . .
C21 C 0.9084(3) 0.50944(16) 0.78300(15) 0.0726(5) Uani 1 1 d . . . . .
H21A H 0.970825 0.485415 0.725528 0.109 Uiso 1 1 calc GR . . . .
H21B H 0.827358 0.452171 0.814081 0.109 Uiso 1 1 calc GR . . . .
H21C H 0.982579 0.515446 0.825626 0.109 Uiso 1 1 calc GR . . . .
C7 C 0.9226(2) 0.31916(15) 0.49457(15) 0.0702(5) Uani 1 1 d . . . . .
H7A H 0.995494 0.297071 0.439310 0.105 Uiso 1 1 calc GR . . . .
H7B H 0.841264 0.260447 0.520203 0.105 Uiso 1 1 calc GR . . . .
H7C H 0.986218 0.325230 0.542548 0.105 Uiso 1 1 calc GR . . . .
C1 C 0.8426(3) 0.74309(18) 0.10951(12) 0.0754(6) Uani 1 1 d . . . . .
H1A H 0.875329 0.675029 0.079748 0.113 Uiso 1 1 calc GR . . . .
H1B H 0.937647 0.789687 0.102514 0.113 Uiso 1 1 calc GR . . . .
H1C H 0.758878 0.789366 0.079223 0.113 Uiso 1 1 calc GR . . . .
C26 C 0.1600(3) 0.92208(17) 1.17525(13) 0.0720(5) Uani 1 1 d . . . . .
H26 H 0.085824 0.951311 1.223952 0.086 Uiso 1 1 calc R . . . .
C25 C 0.2547(3) 0.82105(18) 1.19600(12) 0.0725(5) Uani 1 1 d . . . . .
H25 H 0.244244 0.780778 1.258943 0.087 Uiso 1 1 calc R . . . .
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
C20 O7 C21 116.90(13) . .
C6 O3 C7 116.14(13) . .
C16 O5 C15 115.87(12) . .
C2 O1 C1 116.67(13) . .
C8 N1 C9 128.71(12) . .
C22 N2 C23 128.19(13) . .
C17 C18 C19 128.87(14) . .
N1 C8 C5 125.26(13) . .
O3 C6 C5 113.18(13) . .
O4 C6 O3 121.41(13) . .
O4 C6 C5 125.41(14) . .
C8 C5 C6 118.91(13) . .
C8 C5 C4 122.00(13) . .
C4 C5 C6 119.06(13) . .
N2 C22 C19 125.44(14) . .
C18 C19 C20 119.21(13) . .
C22 C19 C18 121.43(13) . .
C22 C19 C20 119.35(13) . .
O7 C20 C19 113.39(13) . .
O8 C20 O7 121.91(13) . .
O8 C20 C19 124.70(14) . .
C10 C9 N1 117.78(13) . .
C14 C9 N1 123.06(14) . .
C14 C9 C10 119.16(15) . .
C3 C4 C5 129.19(14) . .
O5 C16 C17 113.63(12) . .
O6 C16 O5 121.78(14) . .
O6 C16 C17 124.57(14) . .
C28 C23 N2 122.83(14) . .
C24 C23 N2 118.20(14) . .
C24 C23 C28 118.96(15) . .
O1 C2 C3 113.03(13) . .
O2 C2 O1 122.16(15) . .
O2 C2 C3 124.81(15) . .
C18 C17 C16 123.21(14) . .
C27 C28 C23 119.09(15) . .
C11 C10 C9 120.88(16) . .
C13 C14 C9 118.95(15) . .
C25 C24 C23 121.17(17) . .
C4 C3 C2 123.50(14) . .
C10 C11 C12 119.98(16) . .
C12 C13 C14 121.83(16) . .
C28 C27 C26 121.52(17) . .
C13 C12 C11 119.20(17) . .
C25 C26 C27 119.34(17) . .
C26 C25 C24 119.90(16) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O7 C20 1.3374(19) .
O7 C21 1.4379(19) .
O3 C6 1.343(2) .
O3 C7 1.4386(19) .
O4 C6 1.2144(18) .
O5 C16 1.3403(18) .
O5 C15 1.4329(19) .
O6 C16 1.2112(18) .
O1 C2 1.3473(19) .
O1 C1 1.426(2) .
O8 C20 1.2253(18) .
O2 C2 1.2026(19) .
N1 C8 1.3356(18) .
N1 C9 1.398(2) .
N2 C22 1.3330(19) .
N2 C23 1.404(2) .
C18 C19 1.447(2) .
C18 C17 1.334(2) .
C8 C5 1.372(2) .
C6 C5 1.4646(19) .
C5 C4 1.451(2) .
C22 C19 1.370(2) .
C19 C20 1.463(2) .
C9 C10 1.390(2) .
C9 C14 1.390(2) .
C4 C3 1.328(2) .
C16 C17 1.455(2) .
C23 C28 1.388(2) .
C23 C24 1.384(2) .
C2 C3 1.456(2) .
C28 C27 1.376(2) .
C10 C11 1.371(3) .
C14 C13 1.381(3) .
C24 C25 1.373(3) .
C11 C12 1.383(3) .
C13 C12 1.368(3) .
C27 C26 1.377(2) .
C26 C25 1.369(3) .
