#------------------------------------------------------------------------------
#$Date: 2025-08-19 14:52:15 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301804 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/16/2211664.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_2211664
loop_
_publ_author_name
'Wu, Yun'
'Zhao, Bo'
'Li, Baolong'
_publ_section_title
;
 N-[4-(4-Nitrobenzylideneamino)phenyl]acetamide
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o5677
_journal_page_last               o5678
_journal_paper_doi               10.1107/S1600536806048173
_journal_volume                  62
_journal_year                    2006
_chemical_formula_moiety         'C15 H13 N3 O3'
_chemical_formula_sum            'C15 H13 N3 O3'
_chemical_formula_weight         283.28
_chemical_melting_point          497
_chemical_name_systematic
;
N-(4-(4-nitrobenzylideneamino)phenyl)acetamide
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.0477(8)
_cell_length_b                   15.1868(17)
_cell_length_c                   24.426(3)
_cell_measurement_reflns_used    7894
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      25.3491
_cell_measurement_theta_min      3.0088
_cell_volume                     2614.4(5)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku, 2002)'
_computing_data_reduction        CrystalClear
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku Mercury CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_av_sigmaI/netI    0.0261
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            23604
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.16
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.9797
_exptl_absorpt_correction_T_min  0.9619
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Jacobson, 1998)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.450
_refine_diff_density_min         -0.387
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.152
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2392
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.152
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0634
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0512P)²+2.827P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1385
_refine_ls_wR_factor_ref         0.1421
_reflns_number_gt                2200
_reflns_number_total             2392
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            wn2091.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2211664
_cod_database_fobs_code          2211664
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, z'
'x, -y+1/2, z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, -z'
'-x, y-1/2, -z-1/2'
'x-1/2, y, -z-1/2'
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_refinement_flags
_atom_site_occupancy
O O1 0.3086(3) 0.07263(12) 0.67188(7) 0.0363(5) Uani d . 1
O O2 0.3856(3) -0.03098(12) 0.61546(8) 0.0385(5) Uani d . 1
O O3 0.4621(3) 0.71569(11) 0.29691(7) 0.0348(5) Uani d . 1
N N1 0.3465(3) 0.04611(14) 0.62565(8) 0.0285(5) Uani d . 1
N N2 0.3429(3) 0.37099(13) 0.45248(8) 0.0242(5) Uani d . 1
N N3 0.3848(3) 0.58092(12) 0.26271(8) 0.0237(5) Uani d . 1
H H3B 0.3595 0.5529 0.2320 0.028 Uiso calc R 1
C C1 0.3482(3) 0.22741(15) 0.49499(9) 0.0224(5) Uani d . 1
C C2 0.3512(3) 0.13726(15) 0.48497(10) 0.0253(5) Uani d . 1
H H2A 0.3561 0.1165 0.4483 0.030 Uiso calc R 1
C C3 0.3471(3) 0.07745(15) 0.52765(10) 0.0260(5) Uani d . 1
H H3A 0.3459 0.0159 0.5208 0.031 Uiso calc R 1
C C4 0.3449(3) 0.10956(15) 0.58038(9) 0.0227(5) Uani d . 1
C C5 0.3440(3) 0.19894(16) 0.59231(9) 0.0243(5) Uani d . 1
H H5A 0.3436 0.2191 0.6291 0.029 Uiso calc R 1
C C6 0.3438(3) 0.25790(16) 0.54911(9) 0.0245(5) Uani d . 1
H H6A 0.3406 0.3194 0.5562 0.029 Uiso calc R 1
C C7 0.3521(3) 0.28737(16) 0.44817(9) 0.0247(5) Uani d . 1
H H7A 0.3619 0.2627 0.4125 0.030 Uiso calc R 1
C C8 0.3469(3) 0.42199(15) 0.40380(9) 0.0220(5) Uani d . 1
C C9 0.2770(3) 0.39398(15) 0.35312(9) 0.0234(5) Uani d . 1
H H9A 0.2205 0.3374 0.3500 0.028 Uiso calc R 1
C C10 0.2892(3) 0.44732(15) 0.30780(9) 0.0235(5) Uani d . 1
H H10A 0.2417 0.4270 0.2737 0.028 Uiso calc R 1
C C11 0.3703(3) 0.53090(15) 0.31132(9) 0.0214(5) Uani d . 1
C C12 0.4357(3) 0.56071(15) 0.36204(9) 0.0247(5) Uani d . 1
H H12A 0.4892 0.6179 0.3654 0.030 Uiso calc R 1
C C13 0.4221(3) 0.50630(15) 0.40751(9) 0.0244(5) Uani d . 1
H H13A 0.4653 0.5272 0.4420 0.029 Uiso calc R 1
C C14 0.4334(3) 0.66774(15) 0.25763(10) 0.0243(5) Uani d . 1
C C15 0.4494(4) 0.70047(17) 0.19978(10) 0.0312(6) Uani d . 1
H H15A 0.4858 0.7627 0.2000 0.047 Uiso calc R 1
H H15B 0.3268 0.6938 0.1813 0.047 Uiso calc R 1
H H15C 0.5459 0.6662 0.1803 0.047 Uiso calc R 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
O2 N1 O1 123.2(2)
O2 N1 C4 118.4(2)
O1 N1 C4 118.4(2)
C7 N2 C8 118.2(2)
C14 N3 C11 127.77(19)
C14 N3 H3B 116.1
C11 N3 H3B 116.1
C2 C1 C6 119.4(2)
C2 C1 C7 118.4(2)
C6 C1 C7 122.2(2)
C3 C2 C1 120.9(2)
C3 C2 H2A 119.5
C1 C2 H2A 119.5
C4 C3 C2 118.2(2)
C4 C3 H3A 120.9
C2 C3 H3A 120.9
C3 C4 C5 122.9(2)
C3 C4 N1 118.2(2)
C5 C4 N1 119.0(2)
C6 C5 C4 118.2(2)
C6 C5 H5A 120.9
C4 C5 H5A 120.9
C5 C6 C1 120.4(2)
C5 C6 H6A 119.8
C1 C6 H6A 119.8
N2 C7 C1 123.7(2)
N2 C7 H7A 118.2
C1 C7 H7A 118.2
C13 C8 C9 118.2(2)
C13 C8 N2 117.1(2)
C9 C8 N2 124.6(2)
C10 C9 C8 120.8(2)
C10 C9 H9A 119.6
C8 C9 H9A 119.6
C9 C10 C11 120.8(2)
C9 C10 H10A 119.6
C11 C10 H10A 119.6
C10 C11 C12 119.0(2)
C10 C11 N3 117.9(2)
C12 C11 N3 123.2(2)
C13 C12 C11 119.6(2)
C13 C12 H12A 120.2
C11 C12 H12A 120.2
C12 C13 C8 121.5(2)
C12 C13 H13A 119.2
C8 C13 H13A 119.2
O3 C14 N3 123.0(2)
O3 C14 C15 122.0(2)
N3 C14 C15 115.0(2)
C14 C15 H15A 109.5
C14 C15 H15B 109.5
H15A C15 H15B 109.5
C14 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
O1 N1 1.228(3)
O2 N1 1.228(3)
O3 C14 1.221(3)
N1 C4 1.467(3)
N2 C7 1.276(3)
N2 C8 1.419(3)
N3 C14 1.368(3)
N3 C11 1.413(3)
N3 H3B 0.8800
C1 C2 1.391(3)
C1 C6 1.401(3)
C1 C7 1.462(3)
C2 C3 1.383(3)
C2 H2A 0.9500
C3 C4 1.377(3)
C3 H3A 0.9500
C4 C5 1.388(3)
C5 C6 1.384(3)
C5 H5A 0.9500
C6 H6A 0.9500
C7 H7A 0.9500
C8 C13 1.389(3)
C8 C9 1.399(3)
C9 C10 1.374(3)
C9 H9A 0.9500
C10 C11 1.395(3)
C10 H10A 0.9500
C11 C12 1.397(3)
C12 C13 1.388(3)
C12 H12A 0.9500
C13 H13A 0.9500
C14 C15 1.502(3)
C15 H15A 0.9800
C15 H15B 0.9800
C15 H15C 0.9800
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
N3 H3B O1 3_554 0.88 2.43 3.263(3) 157
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
C6 C1 C2 C3 0.9(4)
C7 C1 C2 C3 -179.8(2)
C1 C2 C3 C4 -1.6(4)
C2 C3 C4 C5 0.9(4)
C2 C3 C4 N1 -178.2(2)
O2 N1 C4 C3 13.6(3)
O1 N1 C4 C3 -166.4(2)
O2 N1 C4 C5 -165.5(2)
O1 N1 C4 C5 14.5(3)
C3 C4 C5 C6 0.6(4)
N1 C4 C5 C6 179.6(2)
C4 C5 C6 C1 -1.3(3)
C2 C1 C6 C5 0.6(3)
C7 C1 C6 C5 -178.7(2)
C8 N2 C7 C1 -179.7(2)
C2 C1 C7 N2 177.3(2)
C6 C1 C7 N2 -3.3(4)
C7 N2 C8 C13 -151.3(2)
C7 N2 C8 C9 30.1(3)
C13 C8 C9 C10 2.4(3)
N2 C8 C9 C10 -179.1(2)
C8 C9 C10 C11 -0.4(4)
C9 C10 C11 C12 -1.4(3)
C9 C10 C11 N3 177.6(2)
C14 N3 C11 C10 169.9(2)
C14 N3 C11 C12 -11.1(4)
C10 C11 C12 C13 1.2(3)
N3 C11 C12 C13 -177.8(2)
C11 C12 C13 C8 0.8(4)
C9 C8 C13 C12 -2.6(4)
N2 C8 C13 C12 178.8(2)
C11 N3 C14 O3 -4.0(4)
C11 N3 C14 C15 176.0(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 690781
