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#$Date: 2022-06-24 09:52:44 +0300 (Fri, 24 Jun 2022) $
#$Revision: 276218 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/54/8105487.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_8105487
loop_
_publ_author_name
'Hanifa, Bibi'
'Sirajuddin, Muhammad'
'Lo, Kong Mun'
'Tiekink, Edward R.T.'
_publ_section_title
;
 Crystal structure of 4-[(4-methoxy-2-nitrophenyl)carbamoyl]butanoic acid,
 C12H14N2O6
;
_journal_issue                   6
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1435
_journal_page_last               1437
_journal_paper_doi               10.1515/ncrs-2020-0350
_journal_volume                  235
_journal_year                    2020
_chemical_formula_moiety         'C12 H14 N2 O6'
_chemical_formula_sum            'C12 H14 N2 O6'
_chemical_formula_weight         282.25
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                76.135(5)
_cell_angle_beta                 82.693(6)
_cell_angle_gamma                87.379(7)
_cell_formula_units_Z            2
_cell_length_a                   4.8835(4)
_cell_length_b                   9.2111(7)
_cell_length_c                   14.6655(7)
_cell_measurement_reflns_used    5658
_cell_measurement_temperature    293(1)
_cell_measurement_theta_max      76.3260
_cell_measurement_theta_min      4.9240
_cell_volume                     635.19(8)
_computing_cell_refinement       'CrysAlisPro [1]'
_computing_data_collection       'CrysAlisPro [1]'
_computing_data_reduction        'CrysAlisPro [1]'
_computing_molecular_graphics    'ORTEP-3 for Windows [4]'
_computing_publication_material  'SHELXL-2018/3 [3]'
_computing_structure_refinement  'SHELXL-2018/3 [3]'
_computing_structure_solution    'SHELXT 2014/5 [2]'
_diffrn_ambient_temperature      293(1)
_diffrn_detector_area_resol_mean 5.2558
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14803
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.077
_diffrn_reflns_theta_max         67.077
_diffrn_reflns_theta_min         3.126
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    1.026
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.758
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'CrysAlisPro [1]'
_exptl_crystal_colour            pale-yellow
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_description       prism
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.131
_exptl_crystal_size_mid          0.091
_exptl_crystal_size_min          0.058
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         2267
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0449
_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)+(0.0744P)²+0.1557P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1229
_refine_ls_wR_factor_ref         0.1297
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1969
_reflns_number_total             2267
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2020-0350_suppl.cif
_cod_data_source_block           shelx
_cod_database_code               8105487
_shelx_shelxl_version_number     2018/3
_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   0.877
_shelx_estimated_absorpt_t_max   0.943
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 0.7000(3) 0.57969(19) 0.05405(9) 0.0749(5) Uani 1 1 d D . . . .
H1O H 0.799(6) 0.583(4) 0.0032(14) 0.112 Uiso 1 1 d D U . . .
O2 O 0.9970(3) 0.40397(17) 0.11252(9) 0.0626(4) Uani 1 1 d . . . . .
O3 O 0.8601(3) 0.19436(18) 0.47437(9) 0.0675(5) Uani 1 1 d . . . . .
O4 O 0.4971(3) -0.15120(16) 0.90826(9) 0.0632(4) Uani 1 1 d . . . . .
O5 O 0.0053(3) 0.33983(16) 0.63309(9) 0.0645(4) Uani 1 1 d . . . . .
O6 O -0.0987(3) 0.27358(19) 0.78196(10) 0.0795(5) Uani 1 1 d . . . . .
N1 N 0.4247(3) 0.21163(18) 0.54797(10) 0.0495(4) Uani 1 1 d D . . . .
H1N H 0.269(3) 0.257(2) 0.5398(15) 0.059 Uiso 1 1 d D U . . .
N2 N 0.0423(3) 0.25956(16) 0.70976(10) 0.0469(4) Uani 1 1 d . . . . .
C1 C 0.7882(4) 0.4784(2) 0.12275(11) 0.0461(4) Uani 1 1 d . . . . .
C2 C 0.6057(4) 0.4619(2) 0.21419(11) 0.0474(4) Uani 1 1 d . . . . .
H2A H 0.430617 0.421954 0.207848 0.057 Uiso 1 1 calc R U . . .
H2B H 0.569303 0.560231 0.226627 0.057 Uiso 1 1 calc R U . . .
C3 C 0.7239(3) 0.3617(2) 0.29818(11) 0.0444(4) Uani 1 1 d . . . . .
H3A H 0.761780 0.263015 0.286435 0.053 Uiso 1 1 calc R U . . .
H3B H 0.896825 0.402060 0.306255 0.053 Uiso 1 1 calc R U . . .
C4 C 0.5254(4) 0.3489(2) 0.38768(11) 0.0481(4) Uani 1 1 d . . . . .
H4A H 0.495603 0.447298 0.400506 0.058 Uiso 1 1 calc R U . . .
H4B H 0.349208 0.314741 0.377520 0.058 Uiso 1 1 calc R U . . .
C5 C 0.6247(3) 0.2434(2) 0.47306(11) 0.0436(4) Uani 1 1 d . . . . .
C6 C 0.4441(3) 0.12560(19) 0.63937(11) 0.0410(4) Uani 1 1 d . . . . .
C7 C 0.6483(3) 0.0134(2) 0.65813(12) 0.0442(4) Uani 1 1 d . . . . .
H7 H 0.777368 -0.001931 0.608823 0.053 Uiso 1 1 calc R U . . .
C8 C 0.6613(3) -0.0740(2) 0.74762(12) 0.0461(4) Uani 1 1 d . . . . .
H8 H 0.800277 -0.146443 0.757922 0.055 Uiso 1 1 calc R U . . .
C9 C 0.4703(4) -0.0561(2) 0.82317(12) 0.0456(4) Uani 1 1 d . . . . .
C10 C 0.2700(3) 0.0538(2) 0.80762(11) 0.0448(4) Uani 1 1 d . . . . .
H10 H 0.141883 0.067954 0.857474 0.054 Uiso 1 1 calc R U . . .
C11 C 0.2592(3) 0.14377(18) 0.71717(11) 0.0401(4) Uani 1 1 d . . . . .
C12 C 0.2814(5) -0.1490(3) 0.98342(14) 0.0693(6) Uani 1 1 d . . . . .
H12A H 0.280685 -0.054918 1.000853 0.104 Uiso 1 1 calc R U . . .
H12B H 0.311520 -0.228699 1.037008 0.104 Uiso 1 1 calc R U . . .
H12C H 0.106920 -0.161791 0.962920 0.104 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 0.0181 0.0091 '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 0.0311 0.0180 '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'
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
C1 O1 H1O 111(2) . .
C9 O4 C12 117.22(14) . .
C5 N1 C6 128.85(14) . .
C5 N1 H1N 115.7(15) . .
C6 N1 H1N 115.1(15) . .
O5 N2 O6 121.18(14) . .
O5 N2 C11 120.50(14) . .
O6 N2 C11 118.33(14) . .
O2 C1 O1 122.96(15) . .
O2 C1 C2 123.80(15) . .
O1 C1 C2 113.23(15) . .
C1 C2 C3 114.26(14) . .
C1 C2 H2A 108.7 . .
C3 C2 H2A 108.7 . .
C1 C2 H2B 108.7 . .
C3 C2 H2B 108.7 . .
H2A C2 H2B 107.6 . .
C4 C3 C2 111.06(13) . .
C4 C3 H3A 109.4 . .
C2 C3 H3A 109.4 . .
C4 C3 H3B 109.4 . .
C2 C3 H3B 109.4 . .
H3A C3 H3B 108.0 . .
C5 C4 C3 113.58(14) . .
C5 C4 H4A 108.8 . .
C3 C4 H4A 108.8 . .
C5 C4 H4B 108.8 . .
C3 C4 H4B 108.8 . .
H4A C4 H4B 107.7 . .
O3 C5 N1 124.12(15) . .
O3 C5 C4 123.16(15) . .
N1 C5 C4 112.71(14) . .
N1 C6 C11 122.19(15) . .
N1 C6 C7 121.65(15) . .
C11 C6 C7 116.15(14) . .
C8 C7 C6 121.45(15) . .
C8 C7 H7 119.3 . .
C6 C7 H7 119.3 . .
C7 C8 C9 121.16(15) . .
C7 C8 H8 119.4 . .
C9 C8 H8 119.4 . .
O4 C9 C10 124.64(15) . .
O4 C9 C8 116.43(14) . .
C10 C9 C8 118.93(15) . .
C9 C10 C11 119.89(15) . .
C9 C10 H10 120.1 . .
C11 C10 H10 120.1 . .
C10 C11 C6 122.38(15) . .
C10 C11 N2 114.99(14) . .
C6 C11 N2 122.62(14) . .
O4 C12 H12A 109.5 . .
O4 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
O4 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.302(2) .
O1 H1O 0.830(10) .
O2 C1 1.216(2) .
O3 C5 1.216(2) .
O4 C9 1.360(2) .
O4 C12 1.428(2) .
O5 N2 1.2184(19) .
O6 N2 1.2180(19) .
N1 C5 1.359(2) .
N1 C6 1.396(2) .
N1 H1N 0.857(10) .
N2 C11 1.463(2) .
C1 C2 1.492(2) .
C2 C3 1.513(2) .
C2 H2A 0.9700 .
C2 H2B 0.9700 .
C3 C4 1.513(2) .
C3 H3A 0.9700 .
C3 H3B 0.9700 .
C4 C5 1.509(2) .
C4 H4A 0.9700 .
C4 H4B 0.9700 .
C6 C11 1.400(2) .
C6 C7 1.406(2) .
C7 C8 1.373(2) .
C7 H7 0.9300 .
C8 C9 1.391(2) .
C8 H8 0.9300 .
C9 C10 1.375(2) .
C10 C11 1.392(2) .
C10 H10 0.9300 .
C12 H12A 0.9600 .
C12 H12B 0.9600 .
C12 H12C 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
O2 C1 C2 C3 9.2(3) . . . .
O1 C1 C2 C3 -171.53(17) . . . .
C1 C2 C3 C4 -179.14(16) . . . .
C2 C3 C4 C5 176.77(15) . . . .
C6 N1 C5 O3 2.7(3) . . . .
C6 N1 C5 C4 -176.31(17) . . . .
C3 C4 C5 O3 12.6(3) . . . .
C3 C4 C5 N1 -168.45(16) . . . .
C5 N1 C6 C11 156.71(18) . . . .
C5 N1 C6 C7 -24.5(3) . . . .
N1 C6 C7 C8 -177.97(16) . . . .
C11 C6 C7 C8 0.9(3) . . . .
C6 C7 C8 C9 0.8(3) . . . .
C12 O4 C9 C10 8.4(3) . . . .
C12 O4 C9 C8 -171.37(18) . . . .
C7 C8 C9 O4 178.21(16) . . . .
C7 C8 C9 C10 -1.6(3) . . . .
O4 C9 C10 C11 -179.12(17) . . . .
C8 C9 C10 C11 0.7(3) . . . .
C9 C10 C11 C6 1.1(3) . . . .
C9 C10 C11 N2 -178.33(16) . . . .
N1 C6 C11 C10 177.02(16) . . . .
C7 C6 C11 C10 -1.8(3) . . . .
N1 C6 C11 N2 -3.6(3) . . . .
C7 C6 C11 N2 177.54(15) . . . .
O5 N2 C11 C10 -176.34(16) . . . .
O6 N2 C11 C10 3.9(2) . . . .
O5 N2 C11 C6 4.3(3) . . . .
O6 N2 C11 C6 -175.50(18) . . . .
