#------------------------------------------------------------------------------
#$Date: 2022-08-24 12:00:36 +0300 (Wed, 24 Aug 2022) $
#$Revision: 277378 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/56/8105694.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8105694
loop_
_publ_author_name
'Maluleka, Marole M'
'Mphahlele, Malose J'
_publ_section_title
;
 Crystal structure of (E)-1-(2--nitrophenyl)-3-phenylprop-2-en-1-one,
 C15H11NO3
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              351
_journal_page_last               353
_journal_paper_doi               10.1515/ncrs-2022-0032
_journal_volume                  237
_journal_year                    2022
_chemical_formula_moiety         'C15  H11  N  O3'
_chemical_formula_sum            'C15 H11 N O3'
_chemical_formula_weight         253.25
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     'dual - dual-space method e.g. SHELXD'
_atom_sites_solution_secondary   'dual - dual-space method e.g. SHELXD'
_cell_angle_alpha                90
_cell_angle_beta                 96.0800(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.4092(2)
_cell_length_b                   23.9605(8)
_cell_length_c                   9.4887(3)
_cell_measurement_reflns_used    9494
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.3
_cell_measurement_theta_min      2.75
_cell_measurement_wavelength     0.71073
_cell_volume                     1222.89(7)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture Photon CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0107
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            46990
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_min         3.342
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7039
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.164
_exptl_crystal_size_min          0.121
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2281
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0358
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0336P)²+0.4553P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0864
_refine_ls_wR_factor_ref         0.0888
_reflns_Friedel_coverage         0
_reflns_number_gt                2091
_reflns_number_total             2281
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0032_suppl.cif
_cod_data_source_block           K020
_cod_database_code               8105694
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.966
_olex2_refinement_description
;
1.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2115(2) 0.65511(5) 0.17385(13) 0.0265(3) Uani 1 1 d . . . . .
C2 C 0.1734(2) 0.71158(5) 0.19862(13) 0.0268(3) Uani 1 1 d . . . . .
C3 C 0.3018(3) 0.75327(6) 0.13585(15) 0.0346(3) Uani 1 1 d . . . . .
H3 H 0.272488 0.791456 0.155255 0.042 Uiso 1 1 calc R U . . .
C4 C 0.4731(3) 0.73827(7) 0.04465(16) 0.0402(4) Uani 1 1 d . . . . .
H4 H 0.564084 0.766231 0.001381 0.048 Uiso 1 1 calc R U . . .
C5 C 0.5121(3) 0.68263(7) 0.01636(15) 0.0409(4) Uani 1 1 d . . . . .
H5 H 0.628736 0.672464 -0.047268 0.049 Uiso 1 1 calc R U . . .
C6 C 0.3829(3) 0.64170(6) 0.07984(14) 0.0347(3) Uani 1 1 d . . . . .
H6 H 0.41161 0.603614 0.058951 0.042 Uiso 1 1 calc R U . . .
C7 C 0.0812(2) 0.60745(5) 0.23931(14) 0.0295(3) Uani 1 1 d . . . . .
C8 C 0.1829(2) 0.58635(5) 0.37817(14) 0.0307(3) Uani 1 1 d . . . . .
H8 H 0.089866 0.558842 0.42172 0.037 Uiso 1 1 calc R U . . .
C9 C 0.3969(2) 0.60304(5) 0.44772(13) 0.0274(3) Uani 1 1 d . . . . .
H9 H 0.48529 0.631365 0.404089 0.033 Uiso 1 1 calc R U . . .
C10 C 0.5096(2) 0.58215(5) 0.58452(13) 0.0273(3) Uani 1 1 d . . . . .
C11 C 0.7317(3) 0.60567(6) 0.64539(15) 0.0340(3) Uani 1 1 d . . . . .
H11 H 0.807931 0.634699 0.597251 0.041 Uiso 1 1 calc R U . . .
C12 C 0.8420(3) 0.58710(6) 0.77533(16) 0.0407(4) Uani 1 1 d . . . . .
H12 H 0.993013 0.603489 0.815803 0.049 Uiso 1 1 calc R U . . .
C13 C 0.7334(3) 0.54486(6) 0.84627(15) 0.0408(4) Uani 1 1 d . . . . .
H13 H 0.80954 0.53212 0.935272 0.049 Uiso 1 1 calc R U . . .
C14 C 0.5138(3) 0.52125(6) 0.78737(16) 0.0413(4) Uani 1 1 d . . . . .
H14 H 0.438899 0.492215 0.836159 0.05 Uiso 1 1 calc R U . . .
C15 C 0.4023(3) 0.53951(6) 0.65810(15) 0.0354(3) Uani 1 1 d . . . . .
H15 H 0.251061 0.522933 0.618674 0.043 Uiso 1 1 calc R U . . .
N1 N -0.0103(2) 0.72862(5) 0.29322(12) 0.0307(3) Uani 1 1 d . . . . .
O1 O -0.0475(2) 0.77829(4) 0.30923(13) 0.0504(3) Uani 1 1 d . . . . .
O2 O -0.11979(19) 0.69190(4) 0.35205(11) 0.0408(3) Uani 1 1 d . . . . .
O3 O -0.09393(19) 0.58472(4) 0.17099(12) 0.0439(3) Uani 1 1 d . . . . .
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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -1 0 0.166
-1 1 0 0.125
0 1 -2 0.069
0 -1 2 0.041
0 -1 0 0.06
0 1 0 0.008
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C2 C1 C7 125.56(11) . .
C6 C1 C2 116.97(12) . .
C6 C1 C7 117.47(12) . .
C1 C2 N1 119.74(11) . .
C3 C2 C1 122.52(12) . .
C3 C2 N1 117.73(12) . .
C2 C3 H3 120.6 . .
C4 C3 C2 118.80(14) . .
C4 C3 H3 120.6 . .
C3 C4 H4 120 . .
C5 C4 C3 119.98(14) . .
C5 C4 H4 120 . .
C4 C5 H5 119.8 . .
C6 C5 C4 120.45(13) . .
C6 C5 H5 119.8 . .
C1 C6 H6 119.4 . .
C5 C6 C1 121.26(14) . .
C5 C6 H6 119.4 . .
C8 C7 C1 118.97(11) . .
O3 C7 C1 119.33(12) . .
O3 C7 C8 121.45(13) . .
C7 C8 H8 117.7 . .
C9 C8 C7 124.52(12) . .
C9 C8 H8 117.7 . .
C8 C9 H9 116.7 . .
C8 C9 C10 126.57(12) . .
C10 C9 H9 116.7 . .
C11 C10 C9 119.26(12) . .
C11 C10 C15 118.24(12) . .
C15 C10 C9 122.50(12) . .
C10 C11 H11 119.7 . .
C12 C11 C10 120.63(14) . .
C12 C11 H11 119.7 . .
C11 C12 H12 119.9 . .
C13 C12 C11 120.26(14) . .
C13 C12 H12 119.9 . .
C12 C13 H13 120.1 . .
C14 C13 C12 119.72(13) . .
C14 C13 H13 120.1 . .
C13 C14 H14 119.8 . .
C13 C14 C15 120.45(14) . .
C15 C14 H14 119.8 . .
C10 C15 H15 119.7 . .
C14 C15 C10 120.68(14) . .
C14 C15 H15 119.7 . .
O1 N1 C2 118.67(11) . .
O1 N1 O2 123.30(12) . .
O2 N1 C2 118.03(11) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.3924(18) .
C1 C6 1.3908(18) .
C1 C7 1.5097(18) .
C2 C3 1.3866(19) .
C2 N1 1.4657(16) .
C3 H3 0.95 .
C3 C4 1.381(2) .
C4 H4 0.95 .
C4 C5 1.381(2) .
C5 H5 0.95 .
C5 C6 1.379(2) .
C6 H6 0.95 .
C7 C8 1.4632(19) .
C7 O3 1.2182(16) .
C8 H8 0.95 .
C8 C9 1.3319(19) .
C9 H9 0.95 .
C9 C10 1.4627(18) .
C10 C11 1.3953(19) .
C10 C15 1.3978(19) .
C11 H11 0.95 .
C11 C12 1.385(2) .
C12 H12 0.95 .
C12 C13 1.381(2) .
C13 H13 0.95 .
C13 C14 1.379(2) .
C14 H14 0.95 .
C14 C15 1.380(2) .
C15 H15 0.95 .
N1 O1 1.2194(15) .
N1 O2 1.2275(15) .
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C1 C2 C3 C4 0.4(2) . . . .
C1 C2 N1 O1 -177.24(12) . . . .
C1 C2 N1 O2 2.48(18) . . . .
C1 C7 C8 C9 -5.9(2) . . . .
C2 C1 C6 C5 1.15(19) . . . .
C2 C1 C7 C8 -86.01(16) . . . .
C2 C1 C7 O3 99.65(16) . . . .
C2 C3 C4 C5 0.6(2) . . . .
C3 C2 N1 O1 2.19(18) . . . .
C3 C2 N1 O2 -178.09(12) . . . .
C3 C4 C5 C6 -0.7(2) . . . .
C4 C5 C6 C1 -0.2(2) . . . .
C6 C1 C2 C3 -1.25(19) . . . .
C6 C1 C2 N1 178.16(11) . . . .
C6 C1 C7 C8 94.54(15) . . . .
C6 C1 C7 O3 -79.80(16) . . . .
C7 C1 C2 C3 179.30(12) . . . .
C7 C1 C2 N1 -1.30(19) . . . .
C7 C1 C6 C5 -179.35(12) . . . .
C7 C8 C9 C10 -178.16(12) . . . .
C8 C9 C10 C11 -177.74(13) . . . .
C8 C9 C10 C15 1.7(2) . . . .
C9 C10 C11 C12 179.49(13) . . . .
C9 C10 C15 C14 -179.57(13) . . . .
C10 C11 C12 C13 0.1(2) . . . .
C11 C10 C15 C14 -0.1(2) . . . .
C11 C12 C13 C14 -0.2(2) . . . .
C12 C13 C14 C15 0.1(2) . . . .
C13 C14 C15 C10 0.1(2) . . . .
C15 C10 C11 C12 0.0(2) . . . .
N1 C2 C3 C4 -179.04(12) . . . .
O3 C7 C8 C9 168.30(14) . . . .
