#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:03:29 +0200 (vie 13 de oct de 2017) $
#$Revision: 201974 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/90/2219074.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_2219074
loop_
_publ_author_name
'Fun, Hoong-Kun'
'Jebas, Samuel Robinson'
'Patil, P. S.'
'Dharmaprakash, S. M.'
_publ_section_title
;
 (E)-3-(4-Chlorophenyl)-1-(2-thienyl)prop-2-en-1-one
;
_journal_coeditor_code           IS2316
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1592
_journal_page_last               o1593
_journal_paper_doi               10.1107/S1600536808022782
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C13 H9 Cl O S'
_chemical_formula_moiety         'C13 H9 Cl O S'
_chemical_formula_sum            'C13 H9 Cl O S'
_chemical_formula_weight         248.71
_chemical_name_systematic
;
(E)-3-(4-Chlorophenyl)-1-(2-thienyl)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                 96.735(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.7023(3)
_cell_length_b                   13.3576(8)
_cell_length_c                   14.7017(10)
_cell_measurement_reflns_used    3595
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.76
_cell_measurement_theta_min      2.79
_cell_volume                     1112.09(12)
_computing_cell_refinement       'APEX2 (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD area-detector'
_diffrn_measurement_method       'φ and 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  0.0304
_diffrn_reflns_av_sigmaI/netI    0.0300
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12436
_diffrn_reflns_theta_full        30.13
_diffrn_reflns_theta_max         30.13
_diffrn_reflns_theta_min         2.79
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.503
_exptl_absorpt_correction_T_max  0.9417
_exptl_absorpt_correction_T_min  0.8043
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.761
_refine_diff_density_min         -0.488
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         3238
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0826
_refine_ls_R_factor_gt           0.0680
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0986P)²+1.8996P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1890
_refine_ls_wR_factor_ref         0.1986
_reflns_number_gt                2546
_reflns_number_total             3238
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is2316.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c '
_cod_database_code               2219074
_cod_database_fobs_code          2219074
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 0.90267(12) 1.35871(6) 0.43901(5) 0.0277(2) Uani d . 1
Cl Cl1 0.00412(13) 0.64087(5) 0.29914(5) 0.0299(2) Uani d . 1
O O1 0.9797(4) 1.14167(16) 0.44334(16) 0.0327(5) Uani d . 1
C C2 0.4870(5) 1.4144(2) 0.3764(2) 0.0293(6) Uani d . 1
H H2A 0.3575 1.4550 0.3579 0.035 Uiso calc R 1
C C3 0.4820(5) 1.3077(2) 0.37026(19) 0.0224(5) Uani d . 1
H H3A 0.3505 1.2703 0.3476 0.027 Uiso calc R 1
C C4 0.7018(5) 1.2675(2) 0.40300(18) 0.0223(5) Uani d . 1
C C5 0.7766(5) 1.1625(2) 0.4128(2) 0.0250(6) Uani d . 1
C C6 0.5981(5) 1.0853(2) 0.3844(2) 0.0268(6) Uani d . 1
H H6A 0.4539 1.1042 0.3529 0.032 Uiso calc R 1
C C7 0.6405(5) 0.9890(2) 0.40334(19) 0.0240(5) Uani d . 1
H H7A 0.7868 0.9732 0.4349 0.029 Uiso calc R 1
C C8 0.4777(5) 0.9050(2) 0.37894(18) 0.0222(5) Uani d . 1
C C9 0.2473(5) 0.9190(2) 0.3366(2) 0.0248(6) Uani d . 1
H H9A 0.1911 0.9837 0.3252 0.030 Uiso calc R 1
C C10 0.1021(5) 0.8388(2) 0.31147(19) 0.0238(5) Uani d . 1
H H10A -0.0501 0.8491 0.2827 0.029 Uiso calc R 1
C C1 0.7028(5) 1.4507(2) 0.4124(2) 0.0301(6) Uani d . 1
H H1A 0.7357 1.5184 0.4211 0.036 Uiso calc R 1
C C12 0.4120(5) 0.7255(2) 0.3732(2) 0.0259(6) Uani d . 1
H H12A 0.4659 0.6607 0.3856 0.031 Uiso calc R 1
C C13 0.5557(5) 0.8070(2) 0.39794(19) 0.0238(5) Uani d . 1
H H13A 0.7068 0.7965 0.4277 0.029 Uiso calc R 1
C C11 0.1866(5) 0.7422(2) 0.32979(19) 0.0224(5) Uani d . 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
S1 0.0200(3) 0.0344(4) 0.0281(4) -0.0065(3) 0.0004(3) -0.0013(3)
Cl1 0.0258(4) 0.0293(4) 0.0341(4) -0.0077(3) 0.0020(3) -0.0027(3)
O1 0.0221(10) 0.0339(12) 0.0397(13) -0.0002(8) -0.0060(9) 0.0006(9)
C2 0.0217(13) 0.0321(15) 0.0342(16) 0.0004(11) 0.0034(11) -0.0023(12)
C3 0.0171(11) 0.0235(12) 0.0262(13) -0.0011(9) 0.0012(9) -0.0021(10)
C4 0.0174(11) 0.0281(13) 0.0207(12) -0.0040(10) 0.0001(9) -0.0028(10)
C5 0.0201(12) 0.0304(14) 0.0243(13) -0.0007(10) 0.0014(10) -0.0009(10)
C6 0.0191(12) 0.0287(14) 0.0312(15) -0.0021(10) -0.0029(10) 0.0005(11)
C7 0.0172(11) 0.0281(13) 0.0262(13) -0.0028(10) 0.0007(9) -0.0002(10)
C8 0.0173(11) 0.0266(13) 0.0224(12) 0.0009(9) 0.0016(9) -0.0015(10)
C9 0.0170(12) 0.0288(14) 0.0279(14) 0.0025(10) -0.0003(10) 0.0004(11)
C10 0.0170(11) 0.0307(13) 0.0233(13) 0.0012(10) 0.0004(9) 0.0023(10)
C1 0.0288(14) 0.0307(14) 0.0318(15) -0.0076(11) 0.0072(11) -0.0024(12)
C12 0.0224(13) 0.0252(13) 0.0300(14) 0.0007(10) 0.0031(10) 0.0038(11)
C13 0.0171(11) 0.0279(13) 0.0263(13) 0.0024(10) 0.0018(9) 0.0036(10)
C11 0.0196(12) 0.0256(13) 0.0227(13) -0.0048(10) 0.0050(9) 0.0003(10)
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'
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'
Cl Cl 0.1484 0.1585 '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
C1 S1 C4 92.14(14)
C1 C2 C3 112.8(3)
C1 C2 H2A 123.6
C3 C2 H2A 123.6
C4 C3 C2 110.6(2)
C4 C3 H3A 124.7
C2 C3 H3A 124.7
C3 C4 C5 129.8(2)
C3 C4 S1 111.9(2)
C5 C4 S1 118.2(2)
O1 C5 C4 120.3(3)
O1 C5 C6 122.5(3)
C4 C5 C6 117.2(2)
C7 C6 C5 120.9(3)
C7 C6 H6A 119.5
C5 C6 H6A 119.5
C6 C7 C8 126.2(3)
C6 C7 H7A 116.9
C8 C7 H7A 116.9
C9 C8 C13 118.3(3)
C9 C8 C7 122.6(3)
C13 C8 C7 119.1(2)
C10 C9 C8 121.3(3)
C10 C9 H9A 119.4
C8 C9 H9A 119.4
C9 C10 C11 119.0(2)
C9 C10 H10A 120.5
C11 C10 H10A 120.5
C2 C1 S1 112.5(2)
C2 C1 H1A 123.7
S1 C1 H1A 123.7
C11 C12 C13 118.9(3)
C11 C12 H12A 120.6
C13 C12 H12A 120.6
C12 C13 C8 121.2(2)
C12 C13 H13A 119.4
C8 C13 H13A 119.4
C12 C11 C10 121.3(2)
C12 C11 Cl1 119.3(2)
C10 C11 Cl1 119.3(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C1 1.691(3)
S1 C4 1.713(3)
Cl1 C11 1.735(3)
O1 C5 1.224(3)
C2 C1 1.369(4)
C2 C3 1.428(4)
C2 H2A 0.9300
C3 C4 1.397(4)
C3 H3A 0.9300
C4 C5 1.468(4)
C5 C6 1.474(4)
C6 C7 1.333(4)
C6 H6A 0.9300
C7 C8 1.473(4)
C7 H7A 0.9300
C8 C9 1.398(4)
C8 C13 1.400(4)
C9 C10 1.377(4)
C9 H9A 0.9300
C10 C11 1.393(4)
C10 H10A 0.9300
C1 H1A 0.9300
C12 C11 1.385(4)
C12 C13 1.386(4)
C12 H12A 0.9300
C13 H13A 0.9300
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
C7 H7A O1 . 0.93 2.50 2.825(4) 101
C13 H13A O1 3_776 0.93 2.58 3.389(4) 145
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
C1 C2 C3 C4 0.0(4)
C2 C3 C4 C5 177.7(3)
C2 C3 C4 S1 -0.2(3)
C1 S1 C4 C3 0.2(2)
C1 S1 C4 C5 -177.9(2)
C3 C4 C5 O1 -180.0(3)
S1 C4 C5 O1 -2.3(4)
C3 C4 C5 C6 0.2(5)
S1 C4 C5 C6 177.9(2)
O1 C5 C6 C7 10.0(5)
C4 C5 C6 C7 -170.1(3)
C5 C6 C7 C8 180.0(3)
C6 C7 C8 C9 -4.1(5)
C6 C7 C8 C13 175.3(3)
C13 C8 C9 C10 -2.0(4)
C7 C8 C9 C10 177.5(3)
C8 C9 C10 C11 0.8(4)
C3 C2 C1 S1 0.2(3)
C4 S1 C1 C2 -0.2(3)
C11 C12 C13 C8 -0.6(4)
C9 C8 C13 C12 1.9(4)
C7 C8 C13 C12 -177.6(3)
C13 C12 C11 C10 -0.6(4)
C13 C12 C11 Cl1 -179.6(2)
C9 C10 C11 C12 0.5(4)
C9 C10 C11 Cl1 179.5(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9797670
