##############################################################################
#                                                                            #
# This CIF contains the data for a data article accepted for                 #
# publication in IUCrData. It conforms to the requirements of                #
# Notes for Authors for IUCrData, and has been                               #
# peer reviewed under the auspices of IUCrData.                              #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the data    # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     'SHELXL-2017/1'
_journal_date_recd_electronic     2022-03-09
_journal_date_accepted     2022-03-10
_journal_name_full     'IUCrData'
_journal_year     2022
_journal_volume     7
_journal_issue      3
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     HO
_journal_paper_doi     10.1107/S2414314622002772
_journal_coeditor_code     HB4403
_publ_contact_author_name     'Rao M. Uppu'
_publ_contact_author_address
;
Department of Environmental Toxicology
Southern University and A&M College
Baton Rouge, LA 70813
USA
;
_publ_contact_author_email
;
rao_uppu@subr.edu
;
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;
N-(4-Methoxy-2-nitrophenyl)acetamide
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Hines III, James E.' .
;
Department of Environmental Toxicology
Southern University and A&M College
Baton Rouge, LA 70813
USA
;
    'Deere, Curtistine J.' .
;
Department of Environmental Toxicology
Southern University and A&M College
Baton Rouge, LA 70813
USA
;
    'Vaddi, Poornasai' .
;
Department of Environmental Toxicology
Southern University and A&M College
Baton Rouge, LA 70813
USA
;
    'Kondati, Ranjeeth R.' .
;
Department of Environmental Toxicology
Southern University and A&M College
Baton Rouge, LA 70813
USA
;
    'Fronczek, Frank R.' .
;
Department of Chemistry
Louisiana State University
Baton Rouge, LA 70803
USA
;
    'Uppu, Rao M.' .
;
Department of Environmental Toxicology
Southern University and A&M College
Baton Rouge, LA 70813
USA
;
_publ_section_synopsis
;
In the title compound, the pendant groups differ in their divergence from
coplanarity with the central ring.
;
_chemical_name_systematic
;
N-(4-Methoxy-2-nitrophenyl)acetamide
;
_chemical_name_common     ?
_chemical_formula_moiety     'C9 H10 N2 O4'
_chemical_formula_sum     'C9 H10 N2 O4'
_chemical_formula_iupac     'C9 H10 N2 O4'
_chemical_formula_weight     210.19
_chemical_melting_point     ?
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 21/n'
_space_group_name_Hall     '-P 2yn'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     14.8713(7)
_cell_length_b     3.9563(2)
_cell_length_c     17.2057(9)
_cell_angle_alpha     90
_cell_angle_beta     114.051(3)
_cell_angle_gamma     90
_cell_volume     924.42(8)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2102
_cell_measurement_theta_min     3.32
_cell_measurement_theta_max     66.29
_cell_measurement_temperature     90.0(5)
_exptl_crystal_description     'lath'
_exptl_crystal_colour     'yellow'
_exptl_crystal_size_max     0.420
_exptl_crystal_size_mid     0.060
_exptl_crystal_size_min     0.010
_exptl_crystal_density_diffrn     1.510
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     440
_exptl_absorpt_coefficient_mu     1.029
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al., 2015)
;
_exptl_absorpt_correction_T_min     0.692
_exptl_absorpt_correction_T_max     0.990
_diffrn_ambient_temperature     90.0(5)
_diffrn_radiation_type     CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_source     'I\mS microfocus'
_diffrn_radiation_monochromator     'QUAZAR multilayer optics'
_diffrn_measurement_device_type     'Bruker Kappa APEXII DUO CCD'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     11516
_diffrn_reflns_av_R_equivalents     0.1217
_diffrn_reflns_av_unetI/netI     0.1570
_diffrn_reflns_theta_min     3.323
_diffrn_reflns_theta_max     66.646
_diffrn_reflns_theta_full     66.646
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -17
_diffrn_reflns_limit_h_max     17
_diffrn_reflns_limit_k_min     -4
_diffrn_reflns_limit_k_max     4
_diffrn_reflns_limit_l_min     -20
_diffrn_reflns_limit_l_max     20
_refine_special_details
;
All H atoms were located in
difference maps and those on C were thereafter treated as riding in
geometrically idealized positions with C---H distances 0.95 Å for phenyl and
0.98 Å for methyl. Coordinates of the N---H hydrogen atom were refined.
Uiso(H) values were assigned as 1.2Ueq for the attached atom
(1.5 for methyl).
;
_reflns_number_total     1638
_reflns_number_gt     1211
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0902
_refine_ls_R_factor_gt     0.0707
_refine_ls_wR_factor_gt     0.1866
_refine_ls_wR_factor_ref     0.2029
_refine_ls_goodness_of_fit_ref     1.091
_refine_ls_restrained_S_all     1.091
_refine_ls_number_reflns     1638
_refine_ls_number_parameters     141
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                           'w=1/[σ²(Fo²)+0.2980P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.244
_refine_diff_density_min     -0.271
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
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'
_computing_data_collection
;
APEX2 (Bruker, 2016)
;
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_reduction
;
SAINT (Bruker, 2016)
;
_computing_structure_solution
;
SHELXT2014/5 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2017/1 (Sheldrick, 2015)
;
_computing_molecular_graphics
;
Mercury (Macrae et al., 2020)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
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
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O1 0.58485(18) 0.7604(7) 0.81731(16) 0.0512(7) Uani d 1 . .
    O O2 0.36866(18) 0.2368(6) 0.43490(15) 0.0455(6) Uani d 1 . .
    O O3 0.23210(18) 0.9412(7) 0.67288(16) 0.0529(7) Uani d 1 . .
    O O4 0.16683(18) 0.9595(6) 0.53559(16) 0.0480(7) Uani d 1 . .
    N N1 0.4165(2) 0.7462(7) 0.75182(18) 0.0447(7) Uani d 1 . .
    H H1N 0.363(4) 0.830(11) 0.753(3) 0.054 Uiso d 1 . .
    N N2 0.2326(2) 0.8718(7) 0.60286(18) 0.0416(7) Uani d 1 . .
    C C1 0.4018(3) 0.6185(9) 0.6716(2) 0.0428(8) Uani d 1 . .
    C C2 0.3144(2) 0.6751(8) 0.5992(2) 0.0420(8) Uani d 1 . .
    C C3 0.3005(2) 0.5555(8) 0.5182(2) 0.0415(8) Uani d 1 . .
    H H3A 0.241073 0.602472 0.470197 0.050 Uiso calc 1 . .
    C C4 0.3736(3) 0.3699(8) 0.5092(2) 0.0417(8) Uani d 1 . .
    C C5 0.4605(3) 0.3057(8) 0.5806(2) 0.0431(8) Uani d 1 . .
    H H5 0.511084 0.176401 0.574482 0.052 Uiso calc 1 . .
    C C6 0.4740(3) 0.4264(9) 0.6593(2) 0.0442(8) Uani d 1 . .
    H H6 0.533915 0.378381 0.706654 0.053 Uiso calc 1 . .
    C C7 0.5054(3) 0.8178(8) 0.8187(2) 0.0435(8) Uani d 1 . .
    C C8 0.4928(3) 0.9743(9) 0.8926(2) 0.0475(8) Uani d 1 . .
    H H8A 0.473964 0.799894 0.923540 0.071 Uiso calc 1 . .
    H H8B 0.441299 1.147414 0.872021 0.071 Uiso calc 1 . .
    H H8C 0.554993 1.078496 0.930706 0.071 Uiso calc 1 . .
    C C9 0.2843(3) 0.3245(9) 0.3589(2) 0.0488(9) Uani d 1 . .
    H H9A 0.224837 0.228708 0.361637 0.073 Uiso calc 1 . .
    H H9B 0.292327 0.233462 0.309172 0.073 Uiso calc 1 . .
    H H9C 0.278101 0.571021 0.354165 0.073 Uiso calc 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    O1 C7 . 1.214(4) ?
    O2 C4 . 1.357(4) ?
    O2 C9 . 1.438(4) ?
    O3 N2 . 1.239(4) ?
    O4 N2 . 1.222(4) ?
    N1 C7 . 1.383(5) ?
    N1 C1 . 1.401(5) ?
    N1 H1N . 0.87(5) ?
    N2 C2 . 1.467(4) ?
    C1 C6 . 1.400(5) ?
    C1 C2 . 1.405(5) ?
    C2 C3 . 1.404(5) ?
    C3 C4 . 1.372(5) ?
    C3 H3A . 0.9500 ?
    C4 C5 . 1.395(5) ?
    C5 C6 . 1.371(5) ?
    C5 H5 . 0.9500 ?
    C6 H6 . 0.9500 ?
    C7 C8 . 1.492(5) ?
    C8 H8A . 0.9800 ?
    C8 H8B . 0.9800 ?
    C8 H8C . 0.9800 ?
    C9 H9A . 0.9800 ?
    C9 H9B . 0.9800 ?
    C9 H9C . 0.9800 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C4 O2 C9 . . 117.1(3) ?
    C7 N1 C1 . . 127.4(3) ?
    C7 N1 H1N . . 118(3) ?
    C1 N1 H1N . . 113(3) ?
    O4 N2 O3 . . 122.6(3) ?
    O4 N2 C2 . . 117.9(3) ?
    O3 N2 C2 . . 119.6(3) ?
    C6 C1 N1 . . 121.6(3) ?
    C6 C1 C2 . . 116.2(3) ?
    N1 C1 C2 . . 122.2(3) ?
    C3 C2 C1 . . 122.4(3) ?
    C3 C2 N2 . . 115.6(3) ?
    C1 C2 N2 . . 122.0(3) ?
    C4 C3 C2 . . 119.2(3) ?
    C4 C3 H3A . . 120.4 ?
    C2 C3 H3A . . 120.4 ?
    O2 C4 C3 . . 124.9(3) ?
    O2 C4 C5 . . 115.7(3) ?
    C3 C4 C5 . . 119.4(3) ?
    C6 C5 C4 . . 121.0(3) ?
    C6 C5 H5 . . 119.5 ?
    C4 C5 H5 . . 119.5 ?
    C5 C6 C1 . . 121.7(3) ?
    C5 C6 H6 . . 119.1 ?
    C1 C6 H6 . . 119.1 ?
    O1 C7 N1 . . 123.6(3) ?
    O1 C7 C8 . . 123.8(3) ?
    N1 C7 C8 . . 112.7(3) ?
    C7 C8 H8A . . 109.5 ?
    C7 C8 H8B . . 109.5 ?
    H8A C8 H8B . . 109.5 ?
    C7 C8 H8C . . 109.5 ?
    H8A C8 H8C . . 109.5 ?
    H8B C8 H8C . . 109.5 ?
    O2 C9 H9A . . 109.5 ?
    O2 C9 H9B . . 109.5 ?
    H9A C9 H9B . . 109.5 ?
    O2 C9 H9C . . 109.5 ?
    H9A C9 H9C . . 109.5 ?
    H9B C9 H9C . . 109.5 ?
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C7 N1 C1 C6 . . . . 25.4(5) ?
    C7 N1 C1 C2 . . . . -154.6(3) ?
    C6 C1 C2 C3 . . . . -1.8(5) ?
    N1 C1 C2 C3 . . . . 178.2(3) ?
    C6 C1 C2 N2 . . . . 180.0(3) ?
    N1 C1 C2 N2 . . . . -0.1(5) ?
    O4 N2 C2 C3 . . . . -10.9(4) ?
    O3 N2 C2 C3 . . . . 168.8(3) ?
    O4 N2 C2 C1 . . . . 167.5(3) ?
    O3 N2 C2 C1 . . . . -12.8(5) ?
    C1 C2 C3 C4 . . . . 1.5(5) ?
    N2 C2 C3 C4 . . . . 179.9(3) ?
    C9 O2 C4 C3 . . . . 6.1(5) ?
    C9 O2 C4 C5 . . . . -174.3(3) ?
    C2 C3 C4 O2 . . . . 179.1(3) ?
    C2 C3 C4 C5 . . . . -0.4(5) ?
    O2 C4 C5 C6 . . . . -179.9(3) ?
    C3 C4 C5 C6 . . . . -0.3(5) ?
    C4 C5 C6 C1 . . . . -0.1(5) ?
    N1 C1 C6 C5 . . . . -178.9(3) ?
    C2 C1 C6 C5 . . . . 1.1(5) ?
    C1 N1 C7 O1 . . . . -3.9(6) ?
    C1 N1 C7 C8 . . . . 175.8(3) ?
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
    N1 H1N O3 . 0.87(5) 1.92(5) 2.632(4) 137(4) yes
    C5 H5 O2 3_656 0.95 2.48 3.418(4) 171 yes
    C6 H6 O1 . 0.95 2.30 2.864(4) 117 yes
    C8 H8B O3 2_556 0.98 2.64 3.578(4) 160 yes
    C8 H8C O4 4_686 0.98 2.63 3.546(4) 156 yes
_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     0.672
_shelx_estimated_absorpt_T_max     0.990
