#------------------------------------------------------------------------------
#$Date: 2024-05-06 07:21:48 +0300 (Mon, 06 May 2024) $
#$Revision: 291728 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/30/2023047.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_2023047
loop_
_publ_author_name
'Shi, Xin-Wei'
'Zheng, Shao-Jun'
'Lu, Qiang-Qiang'
'Li, Gen'
'Zhou, Ya-Fu'
_publ_section_title
;
 Synthesis, crystal structure and Hirshfeld surface analysis of
 N-(6-acetyl-1-nitro-naphthalen-2-yl)acetamide.
;
_journal_coeditor_code           ZN2035
_journal_issue                   'Pt 4'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first              347
_journal_page_last               350
_journal_paper_doi               10.1107/S2056989024001609
_journal_volume                  80
_journal_year                    2024
_chemical_formula_iupac          'C14 H12 N2 O4'
_chemical_formula_moiety         'C14 H12 N2 O4'
_chemical_formula_sum            'C14 H12 N2 O4'
_chemical_formula_weight         272.26
_chemical_name_systematic
;
N-(6-Acetyl-1-nitronaphthalen-2-yl)acetamide
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 104.676(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.7649(14)
_cell_length_b                   6.8899(11)
_cell_length_c                   10.6868(18)
_cell_measurement_reflns_used    1846
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.04
_cell_measurement_theta_min      2.40
_cell_volume                     624.31(18)
_computing_cell_refinement
;
SMART (Bruker, 2002)
;
_computing_data_collection
;
SMART (Bruker, 2002)
;
_computing_data_reduction
;
SAINT (Bruker, 2002)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
publcif (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014/7 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014/7 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0163
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4087
_diffrn_reflns_theta_full        25.192
_diffrn_reflns_theta_max         25.192
_diffrn_reflns_theta_min         1.970
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_description       block
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.286
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1229
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0430
_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)+(0.0709P)²+0.1248P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1188
_refine_ls_wR_factor_ref         0.1237
_reflns_number_gt                1079
_reflns_number_total             1229
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            zn2035.cif
_cod_data_source_block           I
_cod_depositor_comments          'Adding full bibliography for 2023047.cif.'
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               2023047
_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   0.977
_shelx_estimated_absorpt_t_max   0.981
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.0705(2) 0.7500 -0.18378(17) 0.0351(4) Uani d 1 . .
H H1 -0.0097 0.7500 -0.2598 0.042 Uiso calc 1 . .
C C2 0.2243(2) 0.7500 -0.19094(18) 0.0376(5) Uani d 1 . .
C C3 0.3449(2) 0.7500 -0.07463(19) 0.0438(5) Uani d 1 . .
H H3 0.4497 0.7500 -0.0786 0.053 Uiso calc 1 . .
C C4 0.3117(2) 0.7500 0.04290(19) 0.0416(5) Uani d 1 . .
H H4 0.3934 0.7500 0.1179 0.050 Uiso calc 1 . .
C C5 0.1084(2) 0.7500 0.16916(16) 0.0319(4) Uani d 1 . .
C C6 -0.0450(2) 0.7500 0.17851(17) 0.0323(4) Uani d 1 . .
C C7 -0.1648(2) 0.7500 0.06065(18) 0.0384(5) Uani d 1 . .
H H7 -0.2703 0.7500 0.0626 0.046 Uiso calc 1 . .
C C8 -0.1267(2) 0.7500 -0.05469(18) 0.0378(5) Uani d 1 . .
H H8 -0.2076 0.7500 -0.1303 0.045 Uiso calc 1 . .
C C9 0.0307(2) 0.7500 -0.06439(17) 0.0321(4) Uani d 1 . .
C C10 0.1533(2) 0.7500 0.05139(17) 0.0320(4) Uani d 1 . .
C C11 0.2589(2) 0.7500 -0.32103(19) 0.0423(5) Uani d 1 . .
C C12 0.4260(3) 0.7500 -0.3295(2) 0.0620(7) Uani d 1 . .
H H12A 0.4321 0.7500 -0.4154 0.074 Uiso d 1 . .
H H12B 0.4769 0.6362 -0.2882 0.074 Uiso d 1 . .
C C13 -0.2245(2) 0.7500 0.3252(2) 0.0440(5) Uani d 1 . .
C C14 -0.2240(3) 0.7500 0.4642(2) 0.0561(6) Uani d 1 . .
H H14A -0.3152 0.7500 0.4775 0.067 Uiso d 1 . .
H H14B -0.1689 0.8561 0.5077 0.067 Uiso d 1 . .
N N1 0.23711(18) 0.7500 0.28778(14) 0.0398(4) Uani d 1 . .
N N2 -0.07930(18) 0.7500 0.29967(15) 0.0389(4) Uani d 1 . .
H H2 0.0005 0.7500 0.3659 0.047 Uiso calc 1 . .
O O1 0.15177(18) 0.7500 -0.41834(14) 0.0603(5) Uani d 1 . .
O O2 -0.34453(19) 0.7500 0.24224(16) 0.0925(8) Uani d 1 . .
O O3 0.28721(15) 0.5958(2) 0.33316(11) 0.0761(5) Uani 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C9 . . 121.65(17) ?
C2 C1 H1 . . 119.2 ?
C9 C1 H1 . . 119.2 ?
C1 C2 C3 . . 118.58(17) ?
C1 C2 C11 . . 119.07(18) ?
C3 C2 C11 . . 122.34(17) ?
C4 C3 C2 . . 121.69(18) ?
C4 C3 H3 . . 119.2 ?
C2 C3 H3 . . 119.2 ?
C3 C4 C10 . . 120.19(17) ?
C3 C4 H4 . . 119.9 ?
C10 C4 H4 . . 119.9 ?
C6 C5 C10 . . 124.35(16) ?
C6 C5 N1 . . 119.30(16) ?
C10 C5 N1 . . 116.35(15) ?
C5 C6 N2 . . 120.69(16) ?
C5 C6 C7 . . 116.93(16) ?
N2 C6 C7 . . 122.38(16) ?
C8 C7 C6 . . 120.58(17) ?
C8 C7 H7 . . 119.7 ?
C6 C7 H7 . . 119.7 ?
C7 C8 C9 . . 122.54(17) ?
C7 C8 H8 . . 118.7 ?
C9 C8 H8 . . 118.7 ?
C1 C9 C8 . . 122.63(17) ?
C1 C9 C10 . . 119.02(17) ?
C8 C9 C10 . . 118.35(17) ?
C5 C10 C4 . . 123.87(17) ?
C5 C10 C9 . . 117.26(16) ?
C4 C10 C9 . . 118.87(17) ?
O1 C11 C12 . . 120.52(18) ?
O1 C11 C2 . . 120.13(18) ?
C12 C11 C2 . . 119.35(18) ?
C11 C12 H12A . . 111.2 ?
C11 C12 H12B . . 108.9 ?
H12A C12 H12B . . 108.6 ?
O2 C13 N2 . . 122.84(19) ?
O2 C13 C14 . . 121.53(19) ?
N2 C13 C14 . . 115.63(17) ?
C13 C14 H14A . . 113.9 ?
C13 C14 H14B . . 111.7 ?
H14A C14 H14B . . 107.9 ?
O3 N1 O3 . 4_575 123.93(18) ?
O3 N1 C5 . . 118.03(9) ?
O3 N1 C5 4_575 . 118.03(9) ?
C13 N2 C6 . . 127.79(16) ?
C13 N2 H2 . . 116.1 ?
C6 N2 H2 . . 116.1 ?
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
C1 C2 . 1.370(3) ?
C1 C9 . 1.405(3) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.413(3) ?
C2 C11 . 1.496(3) ?
C3 C4 . 1.359(3) ?
C3 H3 . 0.9300 ?
C4 C10 . 1.414(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.374(3) ?
C5 C10 . 1.410(3) ?
C5 N1 . 1.468(2) ?
C6 N2 . 1.402(2) ?
C6 C7 . 1.421(3) ?
C7 C8 . 1.356(3) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.410(3) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.418(2) ?
C11 O1 . 1.212(2) ?
C11 C12 . 1.490(3) ?
C12 H12A . 0.9328 ?
C12 H12B . 0.9534 ?
C13 O2 . 1.192(3) ?
C13 N2 . 1.367(2) ?
C13 C14 . 1.484(3) ?
C14 H14A . 0.8470 ?
C14 H14B . 0.9329 ?
N1 O3 . 1.2038(14) ?
N1 O3 4_575 1.2038(14) ?
N2 H2 . 0.8600 ?
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
N2 H2 O1 1_556 0.86 2.35 3.177(2) 161.1
C7 H7 O2 . 0.93 2.18 2.792(2) 122.7
C4 H4 O2 1_655 0.93 2.34 3.219(2) 156.7
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
C9 C1 C2 C3 . . . . 0.000000 ?
C9 C1 C2 C11 . . . . 180.000000 ?
C1 C2 C3 C4 . . . . 0.000000 ?
C11 C2 C3 C4 . . . . 180.000000 ?
C2 C3 C4 C10 . . . . 0.000000 ?
C10 C5 C6 N2 . . . . 180.000000 ?
N1 C5 C6 N2 . . . . 0.000000 ?
C10 C5 C6 C7 . . . . 0.000000 ?
N1 C5 C6 C7 . . . . 180.000000 ?
C5 C6 C7 C8 . . . . 0.000000 ?
N2 C6 C7 C8 . . . . 180.000000 ?
C6 C7 C8 C9 . . . . 0.000000 ?
C2 C1 C9 C8 . . . . 180.000000 ?
C2 C1 C9 C10 . . . . 0.000000 ?
C7 C8 C9 C1 . . . . 180.000000 ?
C7 C8 C9 C10 . . . . 0.000000 ?
C6 C5 C10 C4 . . . . 180.000000 ?
N1 C5 C10 C4 . . . . 0.000000 ?
C6 C5 C10 C9 . . . . 0.000000 ?
N1 C5 C10 C9 . . . . 180.000000 ?
C3 C4 C10 C5 . . . . 180.000000 ?
C3 C4 C10 C9 . . . . 0.0 ?
C1 C9 C10 C5 . . . . 180.000000 ?
C8 C9 C10 C5 . . . . 0.0 ?
C1 C9 C10 C4 . . . . 0.000000 ?
C8 C9 C10 C4 . . . . 180.0 ?
C1 C2 C11 O1 . . . . 0.000000 ?
C3 C2 C11 O1 . . . . 180.000000 ?
C1 C2 C11 C12 . . . . 180.000000 ?
C3 C2 C11 C12 . . . . 0.000000 ?
C6 C5 N1 O3 . . . . 90.34(15) ?
C10 C5 N1 O3 . . . . -89.66(15) ?
C6 C5 N1 O3 . . . 4_575 -90.34(15) ?
C10 C5 N1 O3 . . . 4_575 89.66(15) ?
O2 C13 N2 C6 . . . . 0.000000 ?
C14 C13 N2 C6 . . . . 180.000000 ?
C5 C6 N2 C13 . . . . 180.000000 ?
C7 C6 N2 C13 . . . . 0.000000 ?
