#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:52:15 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301804 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/46/2214650.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_2214650
loop_
_publ_author_name
'Sarojini, B. K.'
'Narayana,  B.'
'Vijesh, A. M.'
'Yathirajan, H. S.'
'Bolte, Michael'
_publ_section_title
;
 (2E)-1-(3-Methyl-2-thienyl)-3-(3-nitrophenyl)prop-2-en-1-one
;
_journal_coeditor_code           FL2146
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3656
_journal_page_last               o3656
_journal_paper_doi               10.1107/S1600536807035453
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C14 H11 N O3 S'
_chemical_formula_moiety         'C14 H11 N O3 S'
_chemical_formula_sum            'C14 H11 N O3 S'
_chemical_formula_weight         273.30
_chemical_name_systematic
;
(2E)-1-(3-Methyl-2-thienyl)-3-(3-nitrophenyl)prop-2-en-1-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 108.130(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.9340(18)
_cell_length_b                   5.4166(4)
_cell_length_c                   17.789(2)
_cell_measurement_reflns_used    6618
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.3
_cell_measurement_theta_min      4.0
_cell_volume                     1276.0(2)
_computing_cell_refinement       X-Area
_computing_data_collection       'X-Area (Stoe & Cie, 2001)'
_computing_data_reduction        X-Area
_computing_molecular_graphics
'XP in SHELXTL-Plus (Sheldrick, 1991) and PLATON (Spek, 2003)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'STOE IPDS II two-circle diffractometer'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0599
_diffrn_reflns_av_sigmaI/netI    0.0423
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            6347
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         3.95
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.256
_exptl_absorpt_correction_T_max  0.8869
_exptl_absorpt_correction_T_min  0.8848
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(MULABS; Spek, 2003; Blessing, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.48
_refine_diff_density_max         0.652
_refine_diff_density_min         -0.503
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2252
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0647
_refine_ls_R_factor_gt           0.0588
_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)+(0.0815P)²+1.8590P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1565
_refine_ls_wR_factor_ref         0.1605
_reflns_number_gt                1989
_reflns_number_total             2252
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fl2146.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2214650
_cod_database_fobs_code          2214650
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, 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
S S1 0.65303(5) 0.90494(15) 0.09287(4) 0.0336(3) Uani d . 1
N N1 0.53891(18) 0.0052(5) 0.33857(14) 0.0337(6) Uani d . 1
O O1 0.92587(15) 0.6119(4) 0.17453(14) 0.0389(6) Uani d . 1
O O2 0.51014(18) -0.1315(6) 0.38191(15) 0.0560(7) Uani d . 1
O O3 0.48346(16) 0.1519(5) 0.29313(14) 0.0430(6) Uani d . 1
C C1 0.8357(2) 0.6517(5) 0.16477(16) 0.0262(6) Uani d . 1
C C2 0.7792(2) 0.4971(5) 0.20648(15) 0.0246(6) Uani d . 1
H H2 0.7098 0.5291 0.1991 0.030 Uiso calc R 1
C C3 0.8258(2) 0.3148(5) 0.25392(15) 0.0240(6) Uani d . 1
H H3 0.8950 0.2903 0.2588 0.029 Uiso calc R 1
C C11 0.7828(2) 0.8523(5) 0.11302(16) 0.0264(6) Uani d . 1
C C12 0.8250(2) 1.0284(5) 0.07533(16) 0.0312(7) Uani d . 1
C C13 0.7517(2) 1.1975(6) 0.03129(16) 0.0345(7) Uani d . 1
H H13 0.7670 1.3292 0.0017 0.041 Uiso calc R 1
C C14 0.6564(3) 1.1539(6) 0.03523(17) 0.0357(7) Uani d . 1
H H14 0.5990 1.2511 0.0089 0.043 Uiso calc R 1
C C15 0.9313(3) 1.0447(6) 0.08332(18) 0.0397(8) Uani d . 1
H H15A 0.9700 1.0738 0.1389 0.060 Uiso calc R 1
H H15B 0.9425 1.1815 0.0510 0.060 Uiso calc R 1
H H15C 0.9536 0.8899 0.0655 0.060 Uiso calc R 1
C C21 0.78249(19) 0.1471(5) 0.29973(15) 0.0227(6) Uani d . 1
C C22 0.6811(2) 0.1600(5) 0.29780(15) 0.0242(6) Uani d . 1
H H22 0.6373 0.2830 0.2674 0.029 Uiso calc R 1
C C23 0.6465(2) -0.0106(5) 0.34115(15) 0.0250(6) Uani d . 1
C C24 0.7056(2) -0.1942(5) 0.38641(16) 0.0284(6) Uani d . 1
H H24 0.6786 -0.3086 0.4150 0.034 Uiso calc R 1
C C25 0.8057(2) -0.2053(6) 0.38861(16) 0.0309(7) Uani d . 1
H H25 0.8486 -0.3295 0.4191 0.037 Uiso calc R 1
C C26 0.8442(2) -0.0355(5) 0.34632(16) 0.0274(6) Uani d . 1
H H26 0.9133 -0.0441 0.3492 0.033 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'
S S 0.1246 0.1234 '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
C14 S1 C11 91.85(15)
O3 N1 O2 123.2(2)
O3 N1 C23 118.8(2)
O2 N1 C23 118.1(3)
O1 C1 C11 120.6(2)
O1 C1 C2 120.2(3)
C11 C1 C2 119.2(2)
C3 C2 C1 120.1(2)
C3 C2 H2 120.0
C1 C2 H2 120.0
C2 C3 C21 127.3(2)
C2 C3 H3 116.3
C21 C3 H3 116.3
C12 C11 C1 127.1(3)
C12 C11 S1 110.6(2)
C1 C11 S1 122.3(2)
C11 C12 C13 111.7(3)
C11 C12 C15 124.5(3)
C13 C12 C15 123.8(3)
C14 C13 C12 113.8(3)
C14 C13 H13 123.1
C12 C13 H13 123.1
C13 C14 S1 112.0(2)
C13 C14 H14 124.0
S1 C14 H14 124.0
C12 C15 H15A 109.5
C12 C15 H15B 109.5
H15A C15 H15B 109.5
C12 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
C26 C21 C22 118.5(2)
C26 C21 C3 118.8(2)
C22 C21 C3 122.6(2)
C23 C22 C21 118.4(3)
C23 C22 H22 120.8
C21 C22 H22 120.8
C24 C23 C22 124.0(3)
C24 C23 N1 118.2(2)
C22 C23 N1 117.8(2)
C23 C24 C25 117.4(3)
C23 C24 H24 121.3
C25 C24 H24 121.3
C24 C25 C26 120.6(3)
C24 C25 H25 119.7
C26 C25 H25 119.7
C25 C26 C21 121.1(3)
C25 C26 H26 119.5
C21 C26 H26 119.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C14 1.703(3)
S1 C11 1.754(3)
N1 O3 1.222(3)
N1 O2 1.223(3)
N1 C23 1.488(3)
O1 C1 1.233(3)
C1 C11 1.466(4)
C1 C2 1.496(4)
C2 C3 1.330(4)
C2 H2 0.9500
C3 C21 1.470(4)
C3 H3 0.9500
C11 C12 1.396(4)
C12 C13 1.414(4)
C12 C15 1.446(5)
C13 C14 1.372(5)
C13 H13 0.9500
C14 H14 0.9500
C15 H15A 0.9800
C15 H15B 0.9800
C15 H15C 0.9800
C21 C26 1.400(4)
C21 C22 1.404(4)
C22 C23 1.383(4)
C22 H22 0.9500
C23 C24 1.379(4)
C24 C25 1.385(4)
C24 H24 0.9500
C25 C26 1.396(4)
C25 H25 0.9500
C26 H26 0.9500
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
O1 C1 C2 C3 -0.4(4)
C11 C1 C2 C3 -179.7(2)
C1 C2 C3 C21 179.5(2)
O1 C1 C11 C12 -5.6(4)
C2 C1 C11 C12 173.7(3)
O1 C1 C11 S1 176.3(2)
C2 C1 C11 S1 -4.4(4)
C14 S1 C11 C12 0.4(2)
C14 S1 C11 C1 178.8(2)
C1 C11 C12 C13 -178.7(3)
S1 C11 C12 C13 -0.4(3)
C1 C11 C12 C15 -1.7(5)
S1 C11 C12 C15 176.6(2)
C11 C12 C13 C14 0.3(4)
C15 C12 C13 C14 -176.8(3)
C12 C13 C14 S1 0.0(3)
C11 S1 C14 C13 -0.2(2)
C2 C3 C21 C26 179.6(3)
C2 C3 C21 C22 0.6(4)
C26 C21 C22 C23 -0.9(4)
C3 C21 C22 C23 178.1(2)
C21 C22 C23 C24 -0.1(4)
C21 C22 C23 N1 180.0(2)
O3 N1 C23 C24 -173.3(3)
O2 N1 C23 C24 6.1(4)
O3 N1 C23 C22 6.6(4)
O2 N1 C23 C22 -173.9(3)
C22 C23 C24 C25 0.5(4)
N1 C23 C24 C25 -179.6(2)
C23 C24 C25 C26 0.1(4)
C24 C25 C26 C21 -1.1(4)
C22 C21 C26 C25 1.5(4)
C3 C21 C26 C25 -177.6(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139072687
