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#$Date: 2024-05-04 04:52:38 +0300 (Sat, 04 May 2024) $
#$Revision: 291491 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/31/2023117.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_2023117
loop_
_publ_author_name
'Shi, Xin-Wei'
'Bai, Ming-sheng'
'Zheng, Shao-Jun'
'Lu, Qiang-Qiang'
'Li, Gen'
'Zhou, Ya-Fu'
_publ_section_title
;
 Crystal structure characterization, Hirshfeld surface analysis, and DFT
 calculation studies of 1-(6-amino-5-nitronaphthalen-2-yl)ethanone
;
_journal_coeditor_code           ZN2036
_journal_issue                   6
_journal_name_full
'Acta Crystallographica Section E Crystallographic Communications'
_journal_paper_doi               10.1107/S2056989024003797
_journal_volume                  80
_journal_year                    2024
_chemical_formula_iupac          'C12 H10 N2 O3'
_chemical_formula_moiety         'C12 H10 N2 O3'
_chemical_formula_sum            'C12 H10 N2 O3'
_chemical_formula_weight         230.22
_chemical_name_systematic
;
1-(6-Amino-5-nitronaphthalen-2-yl)ethanone
;
_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   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                73.338(4)
_cell_angle_beta                 72.167(4)
_cell_angle_gamma                62.966(4)
_cell_formula_units_Z            2
_cell_length_a                   8.1208(13)
_cell_length_b                   8.2262(14)
_cell_length_c                   9.5944(15)
_cell_measurement_reflns_used    1265
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.96
_cell_measurement_theta_min      2.82
_cell_volume                     535.19(15)
_computing_cell_refinement
;
SMART (Bruker, 2002)
;
_computing_data_collection
;
SMART (Bruker, 2002)
;
_computing_data_reduction
;
SAINT (Bruker, 2002)
;
_computing_molecular_graphics
;
SHELXL2014/7 (Sheldrick, 2015b)
;
_computing_publication_material
;
publcif  (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014/7 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014/7 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0132
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3406
_diffrn_reflns_theta_full        24.986
_diffrn_reflns_theta_max         24.986
_diffrn_reflns_theta_min         2.264
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_description       block
_exptl_crystal_F_000             240
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.412
_refine_diff_density_min         -0.299
_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     155
_refine_ls_number_reflns         1884
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0505
_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)+(0.0735P)²+0.2098P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1337
_refine_ls_wR_factor_ref         0.1480
_reflns_number_gt                1448
_reflns_number_total             1884
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            zn2036.cif
_cod_data_source_block           I
_cod_database_code               2023117
_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   0.959
_shelx_estimated_absorpt_t_max   0.984
loop_
_space_group_symop_operation_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
_atom_site_disorder_assembly
_atom_site_disorder_group
C C12 0.0695(3) 0.0991(3) 0.7872(3) 0.0632(7) Uani d 1 . .
H H12A 0.1914 0.0236 0.8117 0.095 Uiso calc 1 . .
H H12B 0.0717 0.0847 0.6908 0.095 Uiso calc 1 . .
H H12C -0.0238 0.0615 0.8599 0.095 Uiso calc 1 . .
C C11 0.0216(3) 0.2974(3) 0.7860(2) 0.0456(5) Uani d 1 . .
C C3 0.1180(3) 0.3996(3) 0.6612(2) 0.0372(4) Uani d 1 . .
C C2 0.0793(3) 0.5851(3) 0.6600(2) 0.0444(5) Uani d 1 . .
H H2 -0.0081 0.6426 0.7383 0.053 Uiso calc 1 . .
C C1 0.1661(3) 0.6831(3) 0.5474(2) 0.0423(5) Uani d 1 . .
H H1 0.1366 0.8052 0.5514 0.051 Uiso calc 1 . .
C C9 0.2999(2) 0.6039(2) 0.4247(2) 0.0324(4) Uani d 1 . .
C C10 0.3356(2) 0.4177(2) 0.42440(19) 0.0328(4) Uani d 1 . .
C C4 0.2454(3) 0.3209(2) 0.5420(2) 0.0357(4) Uani d 1 . .
H H4 0.2726 0.1990 0.5396 0.043 Uiso calc 1 . .
C C5 0.4643(3) 0.3292(2) 0.3033(2) 0.0392(5) Uani d 1 . .
H H5 0.4859 0.2079 0.3040 0.047 Uiso calc 1 . .
C C6 0.5553(3) 0.4150(3) 0.1883(2) 0.0408(5) Uani d 1 . .
H H6 0.6395 0.3514 0.1120 0.049 Uiso calc 1 . .
C C7 0.5262(3) 0.6024(3) 0.1800(2) 0.0380(5) Uani d 1 . .
C C8 0.3990(3) 0.6942(2) 0.2985(2) 0.0357(4) Uani d 1 . .
N N1 0.3732(3) 0.8791(2) 0.2929(2) 0.0489(5) Uani d 1 . .
N N2 0.6247(3) 0.6726(3) 0.05977(18) 0.0538(5) Uani d 1 . .
H H2A 0.6136 0.7843 0.0491 0.065 Uiso calc 1 . .
H H2B 0.6992 0.6062 -0.0071 0.065 Uiso calc 1 . .
O O1 -0.0958(2) 0.3728(2) 0.88712(17) 0.0677(5) Uani d 1 . .
O O2 0.2953(3) 0.9525(2) 0.4026(2) 0.0887(7) Uani d 1 . .
O O3 0.4405(4) 0.9628(2) 0.1795(2) 0.0975(8) 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
O1 C11 C3 . . 120.96(19) ?
O1 C11 C12 . . 119.56(19) ?
C3 C11 C12 . . 119.48(18) ?
C4 C3 C2 . . 117.08(17) ?
C4 C3 C11 . . 122.46(17) ?
C2 C3 C11 . . 120.46(17) ?
C1 C2 C3 . . 122.07(17) ?
C2 C1 C9 . . 121.76(17) ?
C1 C9 C10 . . 116.07(16) ?
C1 C9 C8 . . 126.75(16) ?
C10 C9 C8 . . 117.15(16) ?
C4 C10 C5 . . 119.62(16) ?
C4 C10 C9 . . 120.65(16) ?
C5 C10 C9 . . 119.73(16) ?
C3 C4 C10 . . 122.33(17) ?
C6 C5 C10 . . 122.09(17) ?
C5 C6 C7 . . 121.51(17) ?
N2 C7 C8 . . 126.40(17) ?
N2 C7 C6 . . 115.85(17) ?
C8 C7 C6 . . 117.75(16) ?
C7 C8 N1 . . 118.03(16) ?
C7 C8 C9 . . 121.77(16) ?
N1 C8 C9 . . 120.18(16) ?
O2 N1 O3 . . 118.66(17) ?
O2 N1 C8 . . 120.96(17) ?
O3 N1 C8 . . 120.21(18) ?
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
C12 C11 . 1.492(3) ?
C11 O1 . 1.215(2) ?
C11 C3 . 1.483(3) ?
C3 C4 . 1.373(2) ?
C3 C2 . 1.408(3) ?
C2 C1 . 1.366(3) ?
C1 C9 . 1.416(3) ?
C9 C10 . 1.424(2) ?
C9 C8 . 1.447(3) ?
C10 C4 . 1.398(2) ?
C10 C5 . 1.422(2) ?
C5 C6 . 1.338(3) ?
C6 C7 . 1.431(3) ?
C7 N2 . 1.333(2) ?
C7 C8 . 1.412(3) ?
C8 N1 . 1.425(2) ?
N1 O2 . 1.217(2) ?
N1 O3 . 1.227(2) ?
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 H2B O1 1_654 0.86 2.16 2.988(2) 161.7
N2 H2A O3 2_675 0.86 2.54 3.146(3) 127.8
N2 H2A O3 . 0.86 1.95 2.556(3) 126.5
C6 H6 O1 1_654 0.93 2.57 3.341(2) 140.9
C1 H1 O2 . 0.93 2.11 2.720(3) 121.6
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
O1 C11 C3 C4 . . . . -177.21(19) ?
C12 C11 C3 C4 . . . . 2.8(3) ?
O1 C11 C3 C2 . . . . 2.0(3) ?
C12 C11 C3 C2 . . . . -178.01(19) ?
C4 C3 C2 C1 . . . . -1.1(3) ?
C11 C3 C2 C1 . . . . 179.64(18) ?
C3 C2 C1 C9 . . . . 0.2(3) ?
C2 C1 C9 C10 . . . . 1.1(3) ?
C2 C1 C9 C8 . . . . 179.23(18) ?
C1 C9 C10 C4 . . . . -1.7(3) ?
C8 C9 C10 C4 . . . . -179.93(16) ?
C1 C9 C10 C5 . . . . 178.33(16) ?
C8 C9 C10 C5 . . . . 0.1(3) ?
C2 C3 C4 C10 . . . . 0.6(3) ?
C11 C3 C4 C10 . . . . 179.81(17) ?
C5 C10 C4 C3 . . . . -179.17(17) ?
C9 C10 C4 C3 . . . . 0.8(3) ?
C4 C10 C5 C6 . . . . -179.61(18) ?
C9 C10 C5 C6 . . . . 0.4(3) ?
C10 C5 C6 C7 . . . . -0.8(3) ?
C5 C6 C7 N2 . . . . -179.82(18) ?
C5 C6 C7 C8 . . . . 0.6(3) ?
N2 C7 C8 N1 . . . . -1.2(3) ?
C6 C7 C8 N1 . . . . 178.35(17) ?
N2 C7 C8 C9 . . . . -179.66(18) ?
C6 C7 C8 C9 . . . . -0.2(3) ?
C1 C9 C8 C7 . . . . -178.23(18) ?
C10 C9 C8 C7 . . . . -0.2(3) ?
C1 C9 C8 N1 . . . . 3.3(3) ?
C10 C9 C8 N1 . . . . -178.64(16) ?
C7 C8 N1 O2 . . . . -165.8(2) ?
C9 C8 N1 O2 . . . . 12.8(3) ?
C7 C8 N1 O3 . . . . 9.4(3) ?
C9 C8 N1 O3 . . . . -172.1(2) ?
