##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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data_global
_audit_creation_method     ?
_journal_date_recd_electronic     2008-04-12
_journal_date_accepted     2008-04-15
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue      5
_journal_page_first     o867
_journal_page_last     o868
_journal_paper_category     QO
_journal_coeditor_code     HK2452
_publ_contact_author
;Muhammad Nawaz Tahir
University of Sargodha
Department of Physics
Sargodha
Pakistan
;
_publ_contact_author_email     dmntahir_uos@yahoo.com
_publ_contact_author_fax     '0092 48 32 22 121'
_publ_contact_author_phone     '0092 48 92 30 170'
_publ_section_title
;
(2E)-3-(4-Chlorophenyl)-1-(1H-pyrrol-2-yl)prop-2-en-1-one
;
loop_
    _publ_author_name
    _publ_author_address
    'Bukhari, Mujahid Hussain'
;
Institute of Chemistry,
University of the Punjab,
Lahore 54590
Pakistan
;
    'Siddiqui, Hamid Latif'
;
Institute of Chemistry,
University of the Punjab,
Lahore 54590
Pakistan
;
    'Tahir, M. Nawaz'
;
University of Sargodha,
Department of Physics,
Sargodha
Pakistan
;
    'Chaudhary, Muhammad Ashraf'
;
Department of Chemistry,
F.C. University,
Lahore 54600
Pakistan
;
    'Iqbal, Amjid'
;
Institute of Chemistry,
University of the Punjab,
Lahore 54590
Pakistan
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
(2E)-3-(4-Chlorophenyl)-1-(1H-pyrrol-2-yl)prop-2-en-1-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C13 H10 Cl N O'
_chemical_formula_sum     'C13 H10 Cl N O'
_chemical_formula_iupac     'C13 H10 Cl N O'
_chemical_formula_weight     231.67
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
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'
_cell_length_a     13.0401(7)
_cell_length_b     5.6326(3)
_cell_length_c     15.6857(8)
_cell_angle_alpha     90.00
_cell_angle_beta     94.979(3)
_cell_angle_gamma     90.00
_cell_volume     1147.76(10)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2883
_cell_measurement_theta_min     2.43
_cell_measurement_theta_max     28.73
_cell_measurement_temperature     296(2)
_exptl_crystal_description     prismatic
_exptl_crystal_colour     'light yellow'
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.22
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.341
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     480
_exptl_absorpt_coefficient_mu     0.309
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2005)'
_exptl_absorpt_correction_T_min     0.903
_exptl_absorpt_correction_T_max     0.935
_exptl_special_details
;
;
_diffrn_ambient_temperature     296(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker KappaAPEXII CCD'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     7.30
_diffrn_reflns_number     13745
_diffrn_reflns_av_R_equivalents     0.0260
_diffrn_reflns_av_sigmaI/netI     0.0205
_diffrn_reflns_theta_min     1.57
_diffrn_reflns_theta_max     29.11
_diffrn_reflns_theta_full     29.11
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -17
_diffrn_reflns_limit_h_max     17
_diffrn_reflns_limit_k_min     -7
_diffrn_reflns_limit_k_max     7
_diffrn_reflns_limit_l_min     -21
_diffrn_reflns_limit_l_max     21
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     3081
_reflns_number_gt     2180
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_gt     0.0428
_refine_ls_wR_factor_gt     0.1077
_refine_ls_wR_factor_ref     0.1283
_refine_ls_goodness_of_fit_ref     1.020
_refine_ls_restrained_S_all     1.020
_refine_ls_number_reflns     3081
_refine_ls_number_parameters     185
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     refall
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0533P)²+0.3294P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.292
_refine_diff_density_min     -0.304
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_extinction_expression     ?
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'
    'Cl' 'Cl' 0.1484 0.1585
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'APEX2 (Bruker, 2007)'
_computing_cell_refinement     'APEX2 (Bruker, 2007)'
_computing_data_reduction     'SAINT (Bruker, 2007)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
                  'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003)'
_computing_publication_material
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2003)
;
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
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Cl Cl 0.47349(5) -0.30082(12) 0.06812(4) 0.0972(3) Uani d . 1 . .
    O O1 0.10949(10) 0.4232(2) 0.43283(8) 0.0672(4) Uani d . 1 . .
    N N1 0.05564(11) 0.2306(3) 0.58749(10) 0.0572(4) Uani d . 1 . .
    C C1 0.29765(11) 0.0517(3) 0.26744(10) 0.0464(3) Uani d . 1 . .
    C C2 0.34920(13) -0.1623(3) 0.28485(11) 0.0525(4) Uani d . 1 . .
    C C3 0.40411(13) -0.2692(3) 0.22394(12) 0.0566(4) Uani d . 1 . .
    C C4 0.40726(13) -0.1631(3) 0.14559(11) 0.0563(4) Uani d . 1 . .
    C C5 0.35867(14) 0.0498(3) 0.12645(11) 0.0588(4) Uani d . 1 . .
    C C6 0.30445(13) 0.1551(3) 0.18805(11) 0.0537(4) Uani d . 1 . .
    C C7 0.23600(12) 0.1706(3) 0.32855(10) 0.0503(4) Uani d . 1 . .
    C C8 0.20870(13) 0.0873(3) 0.40137(11) 0.0548(4) Uani d . 1 . .
    C C9 0.14204(12) 0.2253(3) 0.45499(11) 0.0522(4) Uani d . 1 . .
    C C10 0.11764(11) 0.1179(3) 0.53393(10) 0.0501(4) Uani d . 1 . .
    C C11 0.14707(13) -0.0945(3) 0.57282(11) 0.0566(4) Uani d . 1 . .
    C C12 0.10275(15) -0.1076(4) 0.65000(13) 0.0659(5) Uani d . 1 . .
    C C13 0.04627(14) 0.0958(4) 0.65667(12) 0.0668(5) Uani d . 1 . .
    H H2 0.3481(14) -0.236(3) 0.3387(13) 0.066(5) Uiso d . 1 . .
    H H3 0.4387(13) -0.413(3) 0.2358(11) 0.062(5) Uiso d . 1 . .
    H H6 0.2713(14) 0.300(4) 0.1763(12) 0.063(5) Uiso d . 1 . .
    H H5 0.3607(15) 0.124(4) 0.0702(14) 0.075(6) Uiso d . 1 . .
    H H7 0.2116(14) 0.324(4) 0.3102(12) 0.067(5) Uiso d . 1 . .
    H H8 0.2289(15) -0.069(4) 0.4203(13) 0.076(6) Uiso d . 1 . .
    H H1 0.0220(17) 0.353(4) 0.5749(14) 0.073(6) Uiso d . 1 . .
    H H11 0.1896(14) -0.211(3) 0.5521(12) 0.063(5) Uiso d . 1 . .
    H H12 0.1118(15) -0.226(4) 0.6931(14) 0.075(6) Uiso d . 1 . .
    H H13 0.0089(17) 0.150(4) 0.7011(15) 0.091(7) Uiso 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
    Cl 0.1189(5) 0.0979(5) 0.0810(4) 0.0298(3) 0.0442(3) -0.0182(3)
    O1 0.0738(8) 0.0584(7) 0.0716(8) 0.0223(6) 0.0185(6) -0.0044(6)
    N1 0.0521(7) 0.0644(9) 0.0560(8) 0.0095(7) 0.0107(6) -0.0144(7)
    C1 0.0443(7) 0.0442(7) 0.0509(8) 0.0037(6) 0.0063(6) -0.0076(6)
    C2 0.0576(9) 0.0474(8) 0.0535(9) 0.0092(7) 0.0107(7) 0.0012(7)
    C3 0.0576(9) 0.0457(8) 0.0676(11) 0.0115(7) 0.0123(8) -0.0056(7)
    C4 0.0568(9) 0.0561(9) 0.0578(9) 0.0044(7) 0.0144(7) -0.0152(7)
    C5 0.0653(10) 0.0612(10) 0.0512(9) 0.0050(8) 0.0120(7) -0.0006(8)
    C6 0.0584(9) 0.0467(8) 0.0567(9) 0.0107(7) 0.0083(7) 0.0008(7)
    C7 0.0500(8) 0.0475(8) 0.0536(9) 0.0098(6) 0.0062(6) -0.0073(7)
    C8 0.0558(9) 0.0531(9) 0.0565(9) 0.0132(7) 0.0113(7) -0.0078(7)
    C9 0.0481(8) 0.0550(9) 0.0537(9) 0.0078(7) 0.0062(6) -0.0136(7)
    C10 0.0439(7) 0.0546(9) 0.0518(8) 0.0040(6) 0.0048(6) -0.0162(7)
    C11 0.0531(9) 0.0556(9) 0.0614(10) 0.0012(7) 0.0072(7) -0.0107(8)
    C12 0.0647(10) 0.0701(12) 0.0638(11) -0.0064(9) 0.0113(8) -0.0008(10)
    C13 0.0576(10) 0.0844(13) 0.0604(11) -0.0042(9) 0.0163(8) -0.0137(10)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s.
planes) are estimated using the full covariance matrix. The cell e.s.d.'s
are taken into account individually in the estimation of e.s.d.'s in
distances, angles and torsion angles; correlations between e.s.d.'s in
cell parameters are only used when they are defined by crystal symmetry.
An approximate (isotropic) treatment of cell e.s.d.'s is used for
estimating e.s.d.'s involving l.s. planes.
;
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
    Cl C4 . 1.7339(15) ?
    O1 C9 . 1.232(2) ?
    N1 C13 . 1.338(3) ?
    N1 C10 . 1.3711(19) ?
    N1 H1 . 0.83(2) ?
    C1 C6 . 1.384(2) ?
    C1 C2 . 1.396(2) ?
    C1 C7 . 1.465(2) ?
    C2 C3 . 1.381(2) ?
    C2 H2 . 0.94(2) ?
    C3 C4 . 1.370(3) ?
    C3 H3 . 0.938(18) ?
    C4 C5 . 1.377(2) ?
    C5 C6 . 1.380(2) ?
    C5 H5 . 0.98(2) ?
    C6 H6 . 0.94(2) ?
    C7 C8 . 1.312(2) ?
    C7 H7 . 0.96(2) ?
    C8 C9 . 1.481(2) ?
    C8 H8 . 0.96(2) ?
    C9 C10 . 1.438(2) ?
    C10 C11 . 1.382(2) ?
    C11 C12 . 1.388(3) ?
    C11 H11 . 0.937(19) ?
    C12 C13 . 1.371(3) ?
    C12 H12 . 0.95(2) ?
    C13 H13 . 0.94(2) ?
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
    C13 N1 C10 . . 109.55(16) ?
    C13 N1 H1 . . 125.3(15) ?
    C10 N1 H1 . . 124.5(15) ?
    C6 C1 C2 . . 118.16(14) ?
    C6 C1 C7 . . 118.54(14) ?
    C2 C1 C7 . . 123.29(15) ?
    C3 C2 C1 . . 120.73(16) ?
    C3 C2 H2 . . 118.7(12) ?
    C1 C2 H2 . . 120.6(12) ?
    C4 C3 C2 . . 119.22(16) ?
    C4 C3 H3 . . 120.2(11) ?
    C2 C3 H3 . . 120.5(11) ?
    C3 C4 C5 . . 121.75(15) ?
    C3 C4 Cl . . 119.27(13) ?
    C5 C4 Cl . . 118.98(14) ?
    C4 C5 C6 . . 118.40(16) ?
    C4 C5 H5 . . 121.3(12) ?
    C6 C5 H5 . . 120.3(12) ?
    C5 C6 C1 . . 121.72(15) ?
    C5 C6 H6 . . 119.6(12) ?
    C1 C6 H6 . . 118.7(12) ?
    C8 C7 C1 . . 127.72(15) ?
    C8 C7 H7 . . 118.5(12) ?
    C1 C7 H7 . . 113.7(12) ?
    C7 C8 C9 . . 121.58(16) ?
    C7 C8 H8 . . 120.7(12) ?
    C9 C8 H8 . . 117.7(12) ?
    O1 C9 C10 . . 121.80(14) ?
    O1 C9 C8 . . 121.29(16) ?
    C10 C9 C8 . . 116.91(14) ?
    N1 C10 C11 . . 106.62(15) ?
    N1 C10 C9 . . 121.27(15) ?
    C11 C10 C9 . . 132.10(14) ?
    C10 C11 C12 . . 108.08(16) ?
    C10 C11 H11 . . 127.2(12) ?
    C12 C11 H11 . . 124.7(12) ?
    C13 C12 C11 . . 106.80(18) ?
    C13 C12 H12 . . 124.5(13) ?
    C11 C12 H12 . . 128.6(13) ?
    N1 C13 C12 . . 108.94(17) ?
    N1 C13 H13 . . 120.7(15) ?
    C12 C13 H13 . . 130.3(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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C6 C1 C2 C3 . . . . -0.9(2) ?
    C7 C1 C2 C3 . . . . 178.38(16) ?
    C1 C2 C3 C4 . . . . -0.3(3) ?
    C2 C3 C4 C5 . . . . 1.2(3) ?
    C2 C3 C4 Cl . . . . -178.39(13) ?
    C3 C4 C5 C6 . . . . -1.0(3) ?
    Cl C4 C5 C6 . . . . 178.67(14) ?
    C4 C5 C6 C1 . . . . -0.3(3) ?
    C2 C1 C6 C5 . . . . 1.2(3) ?
    C7 C1 C6 C5 . . . . -178.12(15) ?
    C6 C1 C7 C8 . . . . 170.00(17) ?
    C2 C1 C7 C8 . . . . -9.3(3) ?
    C1 C7 C8 C9 . . . . -177.33(15) ?
    C7 C8 C9 O1 . . . . 0.3(3) ?
    C7 C8 C9 C10 . . . . -179.47(15) ?
    C13 N1 C10 C11 . . . . -0.09(19) ?
    C13 N1 C10 C9 . . . . -179.06(15) ?
    O1 C9 C10 N1 . . . . 0.9(2) ?
    C8 C9 C10 N1 . . . . -179.32(14) ?
    O1 C9 C10 C11 . . . . -177.75(17) ?
    C8 C9 C10 C11 . . . . 2.0(3) ?
    N1 C10 C11 C12 . . . . -0.27(19) ?
    C9 C10 C11 C12 . . . . 178.54(17) ?
    C10 C11 C12 C13 . . . . 0.5(2) ?
    C10 N1 C13 C12 . . . . 0.4(2) ?
    C11 C12 C13 N1 . . . . -0.6(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
    N1 H1 O1 3_566 0.83(2) 2.12(2) 2.902(2) 156(2)
    C3 H3 CgA 2_645 0.938(18) 2.897(17) 3.6339(19) 136.4(13)
    C6 H6 CgB 4_554 0.94(2) 2.651(19) 3.4017(19) 137.8(16)
