#------------------------------------------------------------------------------
#$Date: 2018-01-26 10:37:39 +0200 (Fri, 26 Jan 2018) $
#$Revision: 205721 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/23/2242340.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_2242340
loop_
_publ_author_name
'Yaman, Mavişe'
'Almarhoon, Zainab M.'
'Çakmak, Şükriye'
'Kütük, Halil'
'Meral, Güngör'
'Dege, Necmi'
_publ_section_title
;
 Crystal structure of 2,3-dimethoxy-N-(4-nitrophenyl)benzamide
;
_journal_coeditor_code           XU5912
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              41
_journal_page_last               44
_journal_paper_doi               10.1107/S2056989017017741
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac          'C15 H14 N2 O5'
_chemical_formula_moiety         'C15 H14 N2 O5'
_chemical_formula_sum            'C15 H14 N2 O5'
_chemical_formula_weight         302.28
_chemical_name_systematic
;
2,3-Dimethoxy-N-(4-nitrophenyl)benzamide
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                94.198(6)
_cell_angle_beta                 96.189(6)
_cell_angle_gamma                116.053(5)
_cell_formula_units_Z            2
_cell_length_a                   6.9293(5)
_cell_length_b                   7.3270(5)
_cell_length_c                   15.7411(11)
_cell_measurement_reflns_used    12957
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.52
_cell_measurement_theta_min      2.63
_cell_volume                     707.27(9)
_computing_cell_refinement
;
X-AREA (Stoe & Cie, 2002)
;
_computing_data_collection
;
X-AREA (Stoe & Cie, 2002)
;
_computing_data_reduction
;
X-RED32 (Stoe & Cie, 2002)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
WinGX (Farrugia, 2012) and PLATON (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL2017 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'Stoe IPDS 2'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1086
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10204
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_min         2.627
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.9717
_exptl_absorpt_correction_T_min  0.9470
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
(X-RED32; Stoe & Cie, 2002)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_description       prism
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.740
_exptl_crystal_size_mid          0.487
_exptl_crystal_size_min          0.280
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.147
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2776
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0390
_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)+(0.0593P)²+0.0364P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1085
_refine_ls_wR_factor_ref         0.1140
_reflns_number_gt                2011
_reflns_number_total             2776
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            xu5912sup1.cif
_cod_data_source_block           I
_cod_database_code               2242340
_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.
;
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
O O4 0.64070(15) 0.29058(17) 0.80665(6) 0.0545(3) Uani d 1
O O5 0.60933(17) 0.26544(19) 0.97197(7) 0.0616(3) Uani d 1
N N2 0.4382(2) 0.2366(2) 0.64515(8) 0.0511(3) Uani d 1
O O3 0.10391(19) 0.2209(2) 0.63299(8) 0.0808(4) Uani d 1
C C13 0.4424(2) 0.2492(2) 0.83248(9) 0.0471(3) Uani d 1
C C4 0.4797(2) 0.2459(2) 0.56018(9) 0.0459(3) Uani d 1
C C8 0.2622(2) 0.2150(2) 0.77272(10) 0.0488(4) Uani d 1
O O2 0.8200(3) 0.2760(3) 0.30063(10) 0.1064(5) Uani d 1
N N1 0.6417(3) 0.2623(2) 0.30988(11) 0.0768(5) Uani d 1
C C7 0.2601(2) 0.2247(2) 0.67740(10) 0.0517(4) Uani d 1
C C12 0.4247(2) 0.2346(2) 0.91990(10) 0.0507(4) Uani d 1
C C1 0.5861(3) 0.2588(2) 0.39713(10) 0.0570(4) Uani d 1
C C3 0.3267(3) 0.2228(3) 0.49000(10) 0.0549(4) Uani d 1
H H3 0.188086 0.202409 0.498155 0.066 Uiso calc 1
O O1 0.5080(3) 0.2514(3) 0.25036(9) 0.1153(6) Uani d 1
C C5 0.6860(2) 0.2752(2) 0.54688(10) 0.0540(4) Uani d 1
H H5 0.788868 0.291175 0.593672 0.065 Uiso calc 1
C C9 0.0660(2) 0.1701(3) 0.80232(11) 0.0598(4) Uani d 1
H H9 -0.055930 0.146485 0.763333 0.072 Uiso calc 1
C C6 0.7391(3) 0.2808(3) 0.46522(11) 0.0597(4) Uani d 1
H H6 0.876591 0.299130 0.456262 0.072 Uiso calc 1
C C11 0.2278(3) 0.1919(3) 0.94704(10) 0.0610(4) Uani d 1
H H11 0.215193 0.184597 1.005063 0.073 Uiso calc 1
C C2 0.3818(3) 0.2305(3) 0.40828(10) 0.0594(4) Uani d 1
H H2B 0.281017 0.216468 0.361048 0.071 Uiso calc 1
C C10 0.0500(3) 0.1603(3) 0.88803(12) 0.0667(5) Uani d 1
H H10 -0.081928 0.131915 0.906628 0.080 Uiso calc 1
C C14 0.6008(3) 0.2573(3) 1.06211(10) 0.0672(5) Uani d 1
H H14A 0.740231 0.281308 1.091532 0.101 Uiso calc 1
H H14B 0.563274 0.360514 1.084938 0.101 Uiso calc 1
H H14C 0.493006 0.124535 1.070342 0.101 Uiso calc 1
C C15 0.8027(3) 0.5006(3) 0.83037(13) 0.0752(5) Uani d 1
H H15A 0.935274 0.518241 0.810544 0.113 Uiso calc 1
H H15B 0.751827 0.589244 0.804407 0.113 Uiso calc 1
H H15C 0.828921 0.534368 0.891963 0.113 Uiso calc 1
H H2 0.540(3) 0.244(3) 0.6846(12) 0.072(5) Uiso d 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
_geom_angle_publ_flag
C13 O4 C15 113.96(12) ?
C12 O5 C14 117.60(13) ?
C7 N2 C4 129.19(13) ?
C7 N2 H2 113.0(12) ?
C4 N2 H2 117.7(12) ?
O4 C13 C8 120.97(12) ?
O4 C13 C12 118.37(12) ?
C8 C13 C12 120.61(13) ?
C3 C4 C5 119.50(14) ?
C3 C4 N2 123.89(13) ?
C5 C4 N2 116.58(13) ?
C9 C8 C13 118.36(14) ?
C9 C8 C7 116.01(13) ?
C13 C8 C7 125.63(13) ?
O1 N1 O2 123.34(17) y
O1 N1 C1 118.39(18) y
O2 N1 C1 118.27(18) ?
O3 C7 N2 122.79(14) ?
O3 C7 C8 120.31(13) ?
N2 C7 C8 116.90(12) y
O5 C12 C11 125.07(14) ?
O5 C12 C13 115.56(13) ?
C11 C12 C13 119.37(14) ?
C2 C1 C6 121.87(15) ?
C2 C1 N1 119.17(16) y
C6 C1 N1 118.95(16) y
C2 C3 C4 119.64(15) ?
C2 C3 H3 120.2 ?
C4 C3 H3 120.2 ?
C6 C5 C4 120.53(14) ?
C6 C5 H5 119.7 ?
C4 C5 H5 119.7 ?
C10 C9 C8 120.98(15) ?
C10 C9 H9 119.5 ?
C8 C9 H9 119.5 ?
C1 C6 C5 118.91(15) ?
C1 C6 H6 120.5 ?
C5 C6 H6 120.5 ?
C10 C11 C12 119.99(14) ?
C10 C11 H11 120.0 ?
C12 C11 H11 120.0 ?
C1 C2 C3 119.54(15) ?
C1 C2 H2B 120.2 ?
C3 C2 H2B 120.2 ?
C9 C10 C11 120.66(14) ?
C9 C10 H10 119.7 ?
C11 C10 H10 119.7 ?
O5 C14 H14A 109.5 ?
O5 C14 H14B 109.5 ?
H14A C14 H14B 109.5 ?
O5 C14 H14C 109.5 ?
H14A C14 H14C 109.5 ?
H14B C14 H14C 109.5 ?
O4 C15 H15A 109.5 ?
O4 C15 H15B 109.5 ?
H15A C15 H15B 109.5 ?
O4 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_publ_flag
O4 C13 1.3849(16) y
O4 C15 1.441(2) y
O5 C12 1.3612(18) y
O5 C14 1.4311(19) y
N2 C7 1.3547(19) y
N2 C4 1.3983(19) y
N2 H2 0.870(19) ?
O3 C7 1.2115(18) y
C13 C8 1.394(2) ?
C13 C12 1.402(2) ?
C4 C3 1.391(2) ?
C4 C5 1.392(2) ?
C8 C9 1.393(2) ?
C8 C7 1.506(2) ?
O2 N1 1.221(2) y
N1 O1 1.216(2) y
N1 C1 1.465(2) y
C12 C11 1.383(2) ?
C1 C2 1.370(2) ?
C1 C6 1.371(2) ?
C3 C2 1.379(2) ?
C3 H3 0.9300 ?
C5 C6 1.373(2) ?
C5 H5 0.9300 ?
C9 C10 1.370(2) ?
C9 H9 0.9300 ?
C6 H6 0.9300 ?
C11 C10 1.380(2) ?
C11 H11 0.9300 ?
C2 H2B 0.9300 ?
C10 H10 0.9300 ?
C14 H14A 0.9600 ?
C14 H14B 0.9600 ?
C14 H14C 0.9600 ?
C15 H15A 0.9600 ?
C15 H15B 0.9600 ?
C15 H15C 0.9600 ?
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
_geom_hbond_publ_flag
N2 H2 O4 . 0.870(19) 1.924(19) 2.6805(16) 144.6(17) yes
C5 H5 O3 1_655 0.93 2.48 3.2597(19) 141.3 yes
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_publ_flag
C15 O4 C13 C8 107.52(16) y
C15 O4 C13 C12 -74.91(17) y
C7 N2 C4 C3 -6.9(3) y
C7 N2 C4 C5 174.65(15) y
O4 C13 C8 C9 178.74(14) ?
C12 C13 C8 C9 1.2(2) ?
O4 C13 C8 C7 -2.0(2) y
C12 C13 C8 C7 -179.54(15) ?
C4 N2 C7 O3 -0.2(3) ?
C4 N2 C7 C8 179.49(14) ?
C9 C8 C7 O3 9.6(2) ?
C13 C8 C7 O3 -169.65(16) ?
C9 C8 C7 N2 -170.15(14) ?
C13 C8 C7 N2 10.6(2) ?
C14 O5 C12 C11 -1.3(2) ?
C14 O5 C12 C13 178.43(14) ?
O4 C13 C12 O5 0.7(2) ?
C8 C13 C12 O5 178.26(14) ?
O4 C13 C12 C11 -179.54(14) ?
C8 C13 C12 C11 -2.0(2) ?
O1 N1 C1 C2 4.1(3) ?
O2 N1 C1 C2 -175.90(16) ?
O1 N1 C1 C6 -176.93(17) ?
O2 N1 C1 C6 3.1(2) ?
C5 C4 C3 C2 -0.4(2) ?
N2 C4 C3 C2 -178.75(15) ?
C3 C4 C5 C6 -0.2(2) ?
N2 C4 C5 C6 178.27(14) ?
C13 C8 C9 C10 0.2(2) ?
C7 C8 C9 C10 -179.11(16) ?
C2 C1 C6 C5 -0.3(3) ?
N1 C1 C6 C5 -179.30(15) ?
C4 C5 C6 C1 0.6(2) ?
O5 C12 C11 C10 -178.99(15) ?
C13 C12 C11 C10 1.3(2) ?
C6 C1 C2 C3 -0.2(3) ?
N1 C1 C2 C3 178.71(15) ?
C4 C3 C2 C1 0.6(2) ?
C8 C9 C10 C11 -0.9(3) ?
C12 C11 C10 C9 0.1(3) ?

_cod_database_fobs_code 2242340
