##############################################################################
#                                                                            #
# This CIF contains the data for a data article accepted for                 #
# publication in IUCrData. It conforms to the requirements of                #
# Notes for Authors for IUCrData, and has been                               #
# peer reviewed under the auspices of IUCrData.                              #
#                                                                            #
# 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.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the data    # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_global
_audit_creation_method     'PLATON <TABLE ACC> option'
_journal_date_recd_electronic     2016-11-17
_journal_date_accepted     2016-11-22
_journal_name_full     'IUCrData'
_journal_year     2016
_journal_volume     1
_journal_issue     11
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     HO
_journal_paper_doi     10.1107/S2414314616018654
_journal_coeditor_code     XU4018
_publ_contact_author_name     'Dr Muneer Abdoh'
_publ_contact_author_address
;
Department of Physics,
Science College, An-Najah National University,
PO Box 7, Nablus, West Bank, Palestine Territories
;
_publ_contact_author_email
                           'muneer@najah.edu, lokanath@physics.uni-mysore.ac.in'
_publ_contact_author_fax     '+972 9234 5982'
_publ_contact_author_phone     '+972 9234 5982'
_publ_section_title
;
2,5-Bis(4-chlorobenzylidene)cyclopentanone
;
loop_
    _publ_author_name
    'Seranthimata Samshuddin'
    'Naveen, S.'
    'Ananya, L. N.'
    'Vishwanatha, P.'
    'Lokanath, N. K.'
    'Muneer Abdoh'
    xu4018
loop_
    _publ_author_address
;
Department of Chemistry,
SDM Institute of Technology,
Ujire 574 240, India
;
;
Institution of Excellence,
University of Mysore,
Manasagangotri,
Mysuru 570 006, India
;
;
Department of P.G. Studies in Chemistry,
Alva's College, Moodbidri 574 227,
India
;
;
Department of Chemistry,
SDM Degree College (Autonomous),
Ujire 574 240, India
;
;
Department of Studies in Physics,
University of Mysore,
Manasagangotri,
Mysuru 570 006, India
;
;
Department of Physics,
Science College, An-Najah National University,
PO Box 7, Nablus, West Bank, Palestinian Territories
;
_publ_section_synopsis
;
In the crystal of this bis-chalcone compound, the molecules are linked
via weak C---H...O hydrogen bonds, forming  supramolecular chains
propagating along the [100] direction.
;
data_I
_chemical_name_systematic
;
(2E,5E)-2,5-Bis(4-chlorobenzylidene)cyclopentanone
;
_chemical_name_common     ?
_chemical_formula_moiety     'C19 H14 Cl2 O'
_chemical_formula_sum     'C19 H14 Cl2 O'
_chemical_formula_iupac     'C19 H14 Cl2 O'
_chemical_formula_weight     329.20
_chemical_melting_point     432
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P n m a'
_symmetry_space_group_name_Hall     '-P 2ac 2n'
loop_
    _symmetry_equiv_pos_site_id
    _symmetry_equiv_pos_as_xyz
    1 x,y,z
    2 1/2-x,-y,1/2+z
    3 1/2+x,1/2-y,1/2-z
    4 -x,1/2+y,-z
    5 -x,-y,-z
    6 1/2+x,y,1/2-z
    7 1/2-x,1/2+y,1/2+z
    8 x,1/2-y,z
_cell_length_a     6.1029(4)
_cell_length_b     35.7084(18)
_cell_length_c     7.2217(6)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     1573.79(18)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     1063
_cell_measurement_theta_min     2.88
_cell_measurement_theta_max     26.10
_cell_measurement_temperature     296
_cell_special_details
;
;
_exptl_crystal_description     'rectangle'
_exptl_crystal_colour     'colorless'
_exptl_crystal_size_max     0.29
_exptl_crystal_size_mid     0.27
_exptl_crystal_size_min     0.25
_exptl_crystal_size_rad     ?
_exptl_crystal_density_diffrn     1.389
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'Not Measured'
_exptl_crystal_F_000     680
_exptl_absorpt_coefficient_mu     0.411
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2011)
;
_exptl_absorpt_correction_T_min     0.888
_exptl_absorpt_correction_T_max     0.902
_exptl_special_details
;
;
_diffrn_ambient_temperature     296
_diffrn_radiation_type     'MoK\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'Enraf Nonius FR590'
_diffrn_radiation_monochromator     'graphite'
_diffrn_measurement_device_type     'Bruker APEXII'
_diffrn_measurement_method     'CCD rotation images, thick slices'
_diffrn_detector_area_resol_mean     18.4
_diffrn_reflns_number     6328
_diffrn_reflns_av_R_equivalents     0.0343
_diffrn_reflns_av_sigmaI/netI     0.0355
_diffrn_reflns_theta_min     2.88
_diffrn_reflns_theta_max     26.10
_diffrn_reflns_theta_full     26.10
_diffrn_measured_fraction_theta_max     0.996
_diffrn_measured_fraction_theta_full     0.996
_diffrn_reflns_limit_h_min     -7
_diffrn_reflns_limit_h_max     5
_diffrn_reflns_limit_k_min     -43
_diffrn_reflns_limit_k_max     42
_diffrn_reflns_limit_l_min     -4
_diffrn_reflns_limit_l_max     8
_diffrn_reflns_reduction_process
;
;
_refine_special_details
;
 Refinement on F² for ALL reflections except those
 flagged by the user for potential systematic errors.
 Weighted R-factors wR and all goodnesses of fit S
 are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The
 observed criterion of F² > 2sigma(F²) is used only
 for calculating -R-factor-obs 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     1583
_reflns_number_gt     1063
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0771
_refine_ls_R_factor_gt     0.0438
_refine_ls_wR_factor_gt     0.0974
_refine_ls_wR_factor_ref     0.1109
_refine_ls_goodness_of_fit_ref     1.042
_refine_ls_restrained_S_all     1.042
_refine_ls_number_reflns     1583
_refine_ls_number_parameters     103
_refine_ls_number_restraints     0
_refine_ls_number_constraints     ?
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0447P)²+0.4484P] 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     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.195
_refine_diff_density_min     -0.199
_refine_ls_extinction_method     'none'
_refine_ls_abs_structure_details     ?
_refine_ls_abs_structure_Flack     .
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'
    Cl Cl 0.1484 0.1585 ' 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'
_computing_data_collection
;
APEX2 (Bruker, 2011)
;
_computing_cell_refinement
;
SAINT (Bruker, 2011)
;
_computing_data_reduction
;
SAINT (Bruker, 2011)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_molecular_graphics
;
Mercury (Macrae et al., 2008)
;
_computing_publication_material
;
Mercury (Macrae et al., 2008)
;
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_thermal_displace_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Cl Cl1 0.78079(13) 0.52896(2) 1.04515(13) 0.0841(4) Uani d . 1.000 . .
    O O1 0.1615(3) 0.75000 0.8758(3) 0.0438(7) Uani d S 1.000 . .
    C C1 0.6686(4) 0.57327(6) 1.0207(3) 0.0482(8) Uani d . 1.000 . .
    C C2 0.7870(4) 0.60368(6) 1.0815(3) 0.0475(8) Uani d . 1.000 . .
    C C3 0.7013(3) 0.63916(6) 1.0602(3) 0.0425(8) Uani d . 1.000 . .
    C C4 0.4964(3) 0.64510(5) 0.9785(3) 0.0347(7) Uani d . 1.000 . .
    C C5 0.3827(4) 0.61340(5) 0.9195(3) 0.0422(8) Uani d . 1.000 . .
    C C6 0.4653(4) 0.57775(6) 0.9402(3) 0.0509(9) Uani d . 1.000 . .
    C C7 0.3980(3) 0.68207(5) 0.9492(3) 0.0341(7) Uani d . 1.000 . .
    C C8 0.4771(3) 0.71622(5) 0.9844(3) 0.0324(6) Uani d . 1.000 . .
    C C9 0.6917(3) 0.72845(5) 1.0656(3) 0.0411(8) Uani d . 1.000 . .
    C C10 0.3465(4) 0.75000 0.9390(4) 0.0318(9) Uani d S 1.000 . .
    H H1 0.78180 0.65970 1.10110 0.0510 Uiso c R 1.000 . .
    H H2 0.38550 0.55710 0.90050 0.0610 Uiso c R 1.000 . .
    H H3 0.24620 0.61640 0.86410 0.0510 Uiso c R 1.000 . .
    H H4 0.25820 0.68170 0.89810 0.0410 Uiso c R 1.000 . .
    H H5 0.81240 0.71900 0.99180 0.0490 Uiso c R 1.000 . .
    H H7 0.92350 0.60030 1.13630 0.0570 Uiso c R 1.000 . .
    H H8 0.70690 0.71900 1.19090 0.0490 Uiso c R 1.000 . .
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
    Cl1 0.0893(6) 0.0438(4) 0.1191(8) 0.0186(3) -0.0081(5) 0.0048(4)
    O1 0.0301(10) 0.0461(12) 0.0551(16) 0.0000 -0.0091(10) 0.0000
    C1 0.0577(14) 0.0395(12) 0.0474(16) 0.0083(11) 0.0044(13) 0.0044(10)
    C2 0.0426(12) 0.0511(14) 0.0489(17) 0.0045(11) -0.0060(11) 0.0071(11)
    C3 0.0422(12) 0.0399(12) 0.0454(16) -0.0008(10) -0.0064(11) 0.0028(10)
    C4 0.0356(10) 0.0376(11) 0.0308(13) -0.0018(9) 0.0028(10) 0.0018(9)
    C5 0.0413(11) 0.0429(13) 0.0425(16) -0.0042(9) -0.0035(11) -0.0005(10)
    C6 0.0593(15) 0.0366(12) 0.0567(18) -0.0069(11) -0.0052(13) -0.0023(11)
    C7 0.0293(10) 0.0406(12) 0.0323(14) -0.0015(9) -0.0019(9) 0.0012(9)
    C8 0.0313(10) 0.0388(11) 0.0272(12) 0.0001(9) 0.0010(9) 0.0027(9)
    C9 0.0364(11) 0.0400(12) 0.0469(16) -0.0004(9) -0.0127(11) 0.0026(10)
    C10 0.0272(14) 0.0429(16) 0.0254(18) 0.0000 0.0018(13) 0.0000
_geom_special_details
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_1
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    Cl1 C1 . . 1.733(2) .
    O1 C10 . . 1.218(3) .
    C1 C2 . . 1.376(3) no
    C1 C6 . . 1.380(3) no
    C2 C3 . . 1.379(3) no
    C3 C4 . . 1.399(3) no
    C4 C5 . . 1.394(3) no
    C4 C7 . . 1.466(3) no
    C5 C6 . . 1.377(3) no
    C7 C8 . . 1.336(3) no
    C8 C9 . . 1.500(3) no
    C8 C10 . . 1.483(2) no
    C9 C9 . 8_565 1.539(3) no
    C2 H7 . . 0.9300 no
    C3 H1 . . 0.9300 no
    C5 H3 . . 0.9300 no
    C6 H2 . . 0.9300 no
    C7 H4 . . 0.9300 no
    C9 H5 . . 0.9700 no
    C9 H8 . . 0.9700 no
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_2
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    Cl1 C1 C2 . . . 118.72(18) .
    Cl1 C1 C6 . . . 120.27(17) .
    C2 C1 C6 . . . 121.0(2) no
    C1 C2 C3 . . . 119.4(2) no
    C2 C3 C4 . . . 121.69(19) no
    C3 C4 C5 . . . 116.79(18) no
    C3 C4 C7 . . . 124.32(17) no
    C5 C4 C7 . . . 118.89(18) no
    C4 C5 C6 . . . 122.3(2) no
    C1 C6 C5 . . . 118.8(2) no
    C4 C7 C8 . . . 130.29(18) no
    C7 C8 C9 . . . 130.97(17) no
    C7 C8 C10 . . . 120.42(18) no
    C9 C8 C10 . . . 108.60(15) no
    C8 C9 C9 . . 8_565 106.93(15) no
    O1 C10 C8 . . . 125.55(11) .
    O1 C10 C8 . . 8_565 125.55(11) .
    C8 C10 C8 . . 8_565 108.91(19) no
    C1 C2 H7 . . . 120.00 no
    C3 C2 H7 . . . 120.00 no
    C2 C3 H1 . . . 119.00 no
    C4 C3 H1 . . . 119.00 no
    C4 C5 H3 . . . 119.00 no
    C6 C5 H3 . . . 119.00 no
    C1 C6 H2 . . . 121.00 no
    C5 C6 H2 . . . 121.00 no
    C4 C7 H4 . . . 115.00 no
    C8 C7 H4 . . . 115.00 no
    C8 C9 H5 . . . 110.00 no
    C8 C9 H8 . . . 110.00 no
    H5 C9 H8 . . . 109.00 no
    C9 C9 H5 8_565 . . 110.00 no
    C9 C9 H8 8_565 . . 110.00 no
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
    Cl1 C1 C2 C3 . . . . 178.96(17) no
    C6 C1 C2 C3 . . . . -0.5(3) no
    Cl1 C1 C6 C5 . . . . -178.73(18) no
    C2 C1 C6 C5 . . . . 0.7(3) no
    C1 C2 C3 C4 . . . . 0.1(3) no
    C2 C3 C4 C5 . . . . 0.0(3) no
    C2 C3 C4 C7 . . . . -179.0(2) no
    C3 C4 C5 C6 . . . . 0.2(3) no
    C7 C4 C5 C6 . . . . 179.3(2) no
    C3 C4 C7 C8 . . . . 2.5(4) no
    C5 C4 C7 C8 . . . . -176.4(2) no
    C4 C5 C6 C1 . . . . -0.6(3) no
    C4 C7 C8 C9 . . . . -0.1(4) no
    C4 C7 C8 C10 . . . . 178.9(2) no
    C7 C8 C9 C9 . . . 8_565 178.0(2) no
    C10 C8 C9 C9 . . . 8_565 -1.1(2) no
    C7 C8 C10 O1 . . . . 3.0(4) no
    C7 C8 C10 C8 . . . 8_565 -177.4(2) no
    C9 C8 C10 O1 . . . . -177.8(3) no
    C9 C8 C10 C8 . . . 8_565 1.8(3) no
    C8 C9 C9 C8 . . 8_565 8_565 0.0(2) no
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
    _geom_hbond_publ_flag
    C9 H5 O1 1_655 0.97 2.54 3.270(3) 132 yes
_iucr_refine_instructions_details
;
TITL India_sam205_0ma in Pnma
CELL  0.71073   6.1029  35.7084   7.2217   90.000   90.000   90.000
ZERR     8.00   0.0004   0.0018   0.0006    0.000    0.000    0.000
LATT   1
SYMM  1/2 + X, 1/2 - Y, 1/2 - Z
SYMM  - X, 1/2 + Y, - Z
SYMM  1/2 - X, - Y, 1/2 + Z
SFAC  C    H    CL   N    O
UNIT  76   56   8    0    4
MERG   2
OMIT     0   2   0
FMAP   2
PLAN   20
ACTA
BOND   $H
CONF
L.S.   6
TEMP    23.00
WGHT    0.044700    0.448400
FVAR       0.30746
CL1   3    0.780791    0.528956    1.045147    11.00000    0.08934    0.04381 =
         0.11906    0.00484   -0.00812    0.01864
C1    1    0.668587    0.573267    1.020736    11.00000    0.05771    0.03953 =
         0.04742    0.00442    0.00445    0.00833
C2    1    0.787033    0.603683    1.081467    11.00000    0.04259    0.05108 =
         0.04890    0.00711   -0.00601    0.00449
AFIX  43
H7    2    0.923513    0.600345    1.136321    11.00000   -1.20000
AFIX   0
C3    1    0.701325    0.639157    1.060169    11.00000    0.04223    0.03989 =
         0.04535    0.00278   -0.00644   -0.00076
AFIX  43
H1    2    0.781847    0.659656    1.101146    11.00000   -1.20000
AFIX   0
C4    1    0.496415    0.645102    0.978528    11.00000    0.03558    0.03764 =
         0.03082    0.00181    0.00279   -0.00185
C7    1    0.398019    0.682074    0.949244    11.00000    0.02931    0.04061 =
         0.03226    0.00116   -0.00194   -0.00150
AFIX  43
H4    2    0.258208    0.681698    0.898051    11.00000   -1.20000
AFIX   0
C8    1    0.477132    0.716225    0.984359    11.00000    0.03132    0.03883 =
         0.02724    0.00269    0.00097    0.00014
C10   1    0.346496    0.750000    0.939018    10.50000    0.02716    0.04294 =
         0.02536    0.00000    0.00182    0.00000
C5    1    0.382700    0.613405    0.919470    11.00000    0.04134    0.04292 =
         0.04246   -0.00049   -0.00345   -0.00416
AFIX  43
H3    2    0.246244    0.616444    0.864148    11.00000   -1.20000
AFIX   0
C6    1    0.465338    0.577749    0.940175    11.00000    0.05933    0.03664 =
         0.05665   -0.00228   -0.00522   -0.00692
AFIX  43
H2    2    0.385500    0.557065    0.900535    11.00000   -1.20000
AFIX   0
C9    1    0.691654    0.728454    1.065579    11.00000    0.03638    0.04003 =
         0.04693    0.00260   -0.01272   -0.00037
AFIX  23
H5    2    0.812449    0.719014    0.991811    11.00000   -1.20000
H8    2    0.706922    0.719014    1.190863    11.00000   -1.20000
AFIX   0
O1    5    0.161484    0.750000    0.875796    10.50000    0.03005    0.04614 =
         0.05506    0.00000   -0.00906    0.00000
HKLF 4  1.0  1.00  0.00  0.00  0.00  1.00  0.00  0.00  0.00  1.00
REM  India_sam205_0ma in Pnma
REM R1 =  0.0438 for   1063 Fo > 4sig(Fo)  and  0.0771 for all   1583 data
REM    103 parameters refined using      0 restraints
END
WGHT      0.0469      0.4080
REM Highest difference peak  0.195,  deepest hole -0.199,  1-sigma level  0.042
Q1    1   0.7402  0.7500  1.1034  10.50000  0.05    0.20
Q2    1   0.4730  0.6619  0.9243  11.00000  0.05    0.17
Q3    1   0.4798  0.7015  0.9223  11.00000  0.05    0.14
Q4    1   0.4244  0.7309  0.9444  11.00000  0.05    0.14
Q5    1   0.4305  0.7037  1.0285  11.00000  0.05    0.13
Q6    1   0.8794  0.4809  1.0029  11.00000  0.05    0.13
Q7    1   0.7185  0.5537  1.0273  11.00000  0.05    0.13
Q8    1   0.5876  0.7182  1.0120  11.00000  0.05    0.13
Q9    1   0.7182  0.6189  1.1450  11.00000  0.05    0.12
Q10   1   0.8834  0.6616  0.9940  11.00000  0.05    0.12
Q11   1   0.7811  0.6188  1.0048  11.00000  0.05    0.12
Q12   1   0.7430  0.7500  0.9895  10.50000  0.05    0.12
Q13   1   0.1404  0.6206  0.9525  11.00000  0.05    0.11
Q14   1   0.8446  0.5504  0.9903  11.00000  0.05    0.11
Q15   1   0.9965  0.5688  1.2010  11.00000  0.05    0.11
Q16   1   0.7792  0.6663  1.2599  11.00000  0.05    0.11
Q17   1   0.6255  0.5712  0.8766  11.00000  0.05    0.11
Q18   1   1.0397  0.6092  1.0749  11.00000  0.05    0.11
Q19   1   0.7879  0.7131  1.0794  11.00000  0.05    0.11
Q20   1   0.9946  0.7036  1.0351  11.00000  0.05    0.11
;
