##############################################################################
#                                                                            #
# 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 Acta Crystallographica 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.                                       #
#                                                                            #
# 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 journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_global
_audit_creation_method     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2012-01-04
_journal_date_accepted     2012-01-09
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2012
_journal_volume     68
_journal_issue      2
_journal_page_first     o478
_journal_page_last     o479
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536812000827
_journal_coeditor_code     HB6592
_publ_contact_author_name     'Ibrahim Abdul Razak'
_publ_contact_author_address
;
      School of Physics
      Universiti Sains Malaysia
      11800 USM, Penang
      MALAYSIA
;
_publ_contact_author_email     'arazaki@usm.my'
_publ_contact_author_fax     '604 6579150'
_publ_contact_author_phone     '604 6533438'
_publ_section_title
;
10-(4-Methylbenzylidene)anthracen-9(10H)-one
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Abdulrahman I. Almansour' ?
;
Department of Chemistry
College of Sciences
King Saud University
PO Box 2455, Riyadh 11451
Saudi Arabia
;
    'Natarajan Arumugam'
;
Additional correspondence author, e-mail: anatarajan@ksu.edu.sa.
;
;
Department of Chemistry
College of Sciences
King Saud University
PO Box 2455, Riyadh 11451
Saudi Arabia
;
    'Usama Karama' ?
;
Department of Chemistry
College of Sciences
King Saud University
PO Box 2455, Riyadh 11451
Saudi Arabia
;
    'Ibrahim Abdul Razak'
;
Thomson Reuters ResearcherID: A-5599-2009.
;
;
School of Physics
Universiti Sains Malaysia
11800 USM, Penang
Malaysia
;
    'Suhana Arshad' ?
;
School of Physics
Universiti Sains Malaysia
11800 USM, Penang
Malaysia
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
10-(4-Methylbenzylidene)anthracen-9(10H)-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C22 H16 O'
_chemical_formula_sum     'C22 H16 O'
_chemical_formula_iupac     'C22 H16 O'
_chemical_formula_weight     296.35
_chemical_melting_point     ?
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P n a 21'
_symmetry_space_group_name_Hall     'P 2c -2n'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, z+1/2'
    'x+1/2, -y+1/2, z'
    '-x+1/2, y+1/2, z+1/2'
_cell_length_a     7.29590(10)
_cell_length_b     16.3853(2)
_cell_length_c     13.0028(2)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     1554.43(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     8371
_cell_measurement_theta_min     3.13
_cell_measurement_theta_max     31.72
_cell_measurement_temperature     100.0(10)
_exptl_crystal_description     'block'
_exptl_crystal_colour     'yellow'
_exptl_crystal_size_max     0.33
_exptl_crystal_size_mid     0.27
_exptl_crystal_size_min     0.21
_exptl_crystal_density_diffrn     1.266
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     624
_exptl_absorpt_coefficient_mu     0.076
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2009)'
_exptl_absorpt_correction_T_min     0.9751
_exptl_absorpt_correction_T_max     0.9845
_exptl_special_details
;
The crystal was placed in the cold stream of an Oxford Cryosystems Cobra
open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.
;
_diffrn_ambient_temperature     100.0(10)
_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 SMART APEXII CCD'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     20184
_diffrn_reflns_av_R_equivalents     0.0303
_diffrn_reflns_av_sigmaI/netI     0.0192
_diffrn_reflns_theta_min     2.00
_diffrn_reflns_theta_max     31.80
_diffrn_reflns_theta_full     31.80
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -24
_diffrn_reflns_limit_k_max     21
_diffrn_reflns_limit_l_min     -19
_diffrn_reflns_limit_l_max     17
_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 >
σ(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     2757
_reflns_number_gt     2575
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0460
_refine_ls_R_factor_gt     0.0431
_refine_ls_wR_factor_gt     0.1195
_refine_ls_wR_factor_ref     0.1220
_refine_ls_goodness_of_fit_ref     1.092
_refine_ls_restrained_S_all     1.092
_refine_ls_number_reflns     2757
_refine_ls_number_parameters     209
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0831P)²+0.1277P] 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     0.002
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.395
_refine_diff_density_min     -0.189
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details     'Flack (1983), 2319 Friedel pairs'
_refine_ls_abs_structure_Flack     0(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 0.0000
                         '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 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'APEX2 (Bruker, 2009)'
_computing_cell_refinement     'SAINT (Bruker, 2009)'
_computing_data_reduction     'SAINT (Bruker, 2009)'
_computing_structure_solution     'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
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_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O1 0.22961(18) 0.09172(9) 0.36336(11) 0.0332(3) Uani d . 1 1 . .
    C C1 0.34392(19) 0.11506(9) 0.63231(12) 0.0204(3) Uani d . 1 1 . .
    C C2 0.4267(2) 0.07120(10) 0.71248(13) 0.0249(3) Uani d . 1 1 . .
    H H2A 0.4357 0.0949 0.7789 0.030 Uiso calc R 1 1 . .
    C C3 0.4956(2) -0.00689(11) 0.69531(15) 0.0297(4) Uani d . 1 1 . .
    H H3A 0.5527 -0.0357 0.7500 0.036 Uiso calc R 1 1 . .
    C C4 0.4818(2) -0.04321(11) 0.59886(16) 0.0311(4) Uani d . 1 1 . .
    H H4A 0.5270 -0.0969 0.5880 0.037 Uiso calc R 1 1 . .
    C C5 0.4016(2) -0.00049(10) 0.51897(15) 0.0274(3) Uani d . 1 1 . .
    H H5A 0.3917 -0.0250 0.4530 0.033 Uiso calc R 1 1 . .
    C C6 0.3352(2) 0.07847(10) 0.53448(12) 0.0223(3) Uani d . 1 1 . .
    C C7 0.2696(2) 0.12531(10) 0.44437(12) 0.0234(3) Uani d . 1 1 . .
    C C8 0.2672(2) 0.21516(11) 0.45515(12) 0.0239(3) Uani d . 1 1 . .
    C C9 0.2547(3) 0.26344(13) 0.36613(16) 0.0328(4) Uani d . 1 1 . .
    H H9A 0.2415 0.2381 0.3008 0.039 Uiso calc R 1 1 . .
    C C10 0.2613(3) 0.34737(13) 0.37306(18) 0.0384(5) Uani d . 1 1 . .
    H H10A 0.2514 0.3799 0.3129 0.046 Uiso calc R 1 1 . .
    C C11 0.2828(2) 0.38405(12) 0.46872(18) 0.0351(4) Uani d . 1 1 . .
    H H11A 0.2905 0.4418 0.4733 0.042 Uiso calc R 1 1 . .
    C C12 0.2931(2) 0.33765(10) 0.55740(16) 0.0281(3) Uani d . 1 1 . .
    H H12A 0.3071 0.3638 0.6221 0.034 Uiso calc R 1 1 . .
    C C13 0.2829(2) 0.25202(10) 0.55238(13) 0.0227(3) Uani d . 1 1 . .
    C C14 0.2792(2) 0.20019(9) 0.64518(12) 0.0203(3) Uani d . 1 1 . .
    C C15 0.2111(2) 0.23176(9) 0.73396(12) 0.0223(3) Uani d . 1 1 . .
    H H15A 0.1904 0.2890 0.7325 0.027 Uiso calc R 1 1 . .
    C C16 0.1643(2) 0.19219(9) 0.83166(12) 0.0220(3) Uani d . 1 1 . .
    C C17 0.2006(2) 0.23303(10) 0.92404(14) 0.0274(3) Uani d . 1 1 . .
    H H17A 0.2577 0.2851 0.9224 0.033 Uiso calc R 1 1 . .
    C C18 0.1542(2) 0.19832(12) 1.01808(13) 0.0293(3) Uani d . 1 1 . .
    H H18A 0.1828 0.2265 1.0799 0.035 Uiso calc R 1 1 . .
    C C19 0.0662(2) 0.12249(11) 1.02327(13) 0.0269(3) Uani d . 1 1 . .
    C C20 0.0247(2) 0.08341(10) 0.93057(13) 0.0240(3) Uani d . 1 1 . .
    H H20A -0.0385 0.0327 0.9321 0.029 Uiso calc R 1 1 . .
    C C21 0.0736(2) 0.11680(9) 0.83647(12) 0.0223(3) Uani d . 1 1 . .
    H H21A 0.0454 0.0884 0.7748 0.027 Uiso calc R 1 1 . .
    C C22 0.0189(3) 0.08462(15) 1.12512(15) 0.0386(4) Uani d . 1 1 . .
    H H22A 0.0738 0.1168 1.1807 0.058 Uiso calc R 1 1 . .
    H H22B 0.0665 0.0287 1.1276 0.058 Uiso calc R 1 1 . .
    H H22C -0.1146 0.0836 1.1335 0.058 Uiso calc R 1 1 . .
_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
    O1 C7 . 1.224(2) ?
    C1 C2 . 1.403(2) ?
    C1 C6 . 1.408(2) ?
    C1 C14 . 1.482(2) ?
    C2 C3 . 1.393(2) ?
    C2 H2A . 0.9500 ?
    C3 C4 . 1.392(3) ?
    C3 H3A . 0.9500 ?
    C4 C5 . 1.382(3) ?
    C4 H4A . 0.9500 ?
    C5 C6 . 1.396(2) ?
    C5 H5A . 0.9500 ?
    C6 C7 . 1.480(2) ?
    C7 C8 . 1.479(2) ?
    C8 C13 . 1.406(2) ?
    C8 C9 . 1.405(2) ?
    C9 C10 . 1.379(3) ?
    C9 H9A . 0.9500 ?
    C10 C11 . 1.390(4) ?
    C10 H10A . 0.9500 ?
    C11 C12 . 1.383(3) ?
    C11 H11A . 0.9500 ?
    C12 C13 . 1.407(2) ?
    C12 H12A . 0.9500 ?
    C13 C14 . 1.476(2) ?
    C14 C15 . 1.359(2) ?
    C15 C16 . 1.467(2) ?
    C15 H15A . 0.9500 ?
    C16 C17 . 1.400(2) ?
    C16 C21 . 1.403(2) ?
    C17 C18 . 1.390(2) ?
    C17 H17A . 0.9500 ?
    C18 C19 . 1.400(3) ?
    C18 H18A . 0.9500 ?
    C19 C20 . 1.398(2) ?
    C19 C22 . 1.503(3) ?
    C20 C21 . 1.387(2) ?
    C20 H20A . 0.9500 ?
    C21 H21A . 0.9500 ?
    C22 H22A . 0.9800 ?
    C22 H22B . 0.9800 ?
    C22 H22C . 0.9800 ?
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
    C2 C1 C6 . . 118.21(14) ?
    C2 C1 C14 . . 122.37(15) ?
    C6 C1 C14 . . 119.25(14) ?
    C3 C2 C1 . . 120.46(16) ?
    C3 C2 H2A . . 119.8 ?
    C1 C2 H2A . . 119.8 ?
    C4 C3 C2 . . 120.73(15) ?
    C4 C3 H3A . . 119.6 ?
    C2 C3 H3A . . 119.6 ?
    C5 C4 C3 . . 119.43(15) ?
    C5 C4 H4A . . 120.3 ?
    C3 C4 H4A . . 120.3 ?
    C4 C5 C6 . . 120.50(17) ?
    C4 C5 H5A . . 119.8 ?
    C6 C5 H5A . . 119.8 ?
    C5 C6 C1 . . 120.63(15) ?
    C5 C6 C7 . . 118.58(15) ?
    C1 C6 C7 . . 120.60(14) ?
    O1 C7 C8 . . 121.76(15) ?
    O1 C7 C6 . . 121.69(15) ?
    C8 C7 C6 . . 116.42(14) ?
    C13 C8 C9 . . 120.29(16) ?
    C13 C8 C7 . . 120.79(13) ?
    C9 C8 C7 . . 118.89(16) ?
    C10 C9 C8 . . 120.4(2) ?
    C10 C9 H9A . . 119.8 ?
    C8 C9 H9A . . 119.8 ?
    C9 C10 C11 . . 119.57(17) ?
    C9 C10 H10A . . 120.2 ?
    C11 C10 H10A . . 120.2 ?
    C12 C11 C10 . . 120.96(17) ?
    C12 C11 H11A . . 119.5 ?
    C10 C11 H11A . . 119.5 ?
    C11 C12 C13 . . 120.45(18) ?
    C11 C12 H12A . . 119.8 ?
    C13 C12 H12A . . 119.8 ?
    C8 C13 C12 . . 118.33(15) ?
    C8 C13 C14 . . 119.12(14) ?
    C12 C13 C14 . . 122.48(15) ?
    C15 C14 C13 . . 118.82(13) ?
    C15 C14 C1 . . 124.79(14) ?
    C13 C14 C1 . . 116.33(14) ?
    C14 C15 C16 . . 130.74(13) ?
    C14 C15 H15A . . 114.6 ?
    C16 C15 H15A . . 114.6 ?
    C17 C16 C21 . . 118.16(14) ?
    C17 C16 C15 . . 119.18(13) ?
    C21 C16 C15 . . 122.54(14) ?
    C18 C17 C16 . . 120.85(15) ?
    C18 C17 H17A . . 119.6 ?
    C16 C17 H17A . . 119.6 ?
    C17 C18 C19 . . 121.12(15) ?
    C17 C18 H18A . . 119.4 ?
    C19 C18 H18A . . 119.4 ?
    C20 C19 C18 . . 117.66(15) ?
    C20 C19 C22 . . 121.40(16) ?
    C18 C19 C22 . . 120.94(16) ?
    C21 C20 C19 . . 121.62(14) ?
    C21 C20 H20A . . 119.2 ?
    C19 C20 H20A . . 119.2 ?
    C20 C21 C16 . . 120.53(15) ?
    C20 C21 H21A . . 119.7 ?
    C16 C21 H21A . . 119.7 ?
    C19 C22 H22A . . 109.5 ?
    C19 C22 H22B . . 109.5 ?
    H22A C22 H22B . . 109.5 ?
    C19 C22 H22C . . 109.5 ?
    H22A C22 H22C . . 109.5 ?
    H22B C22 H22C . . 109.5 ?
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) ?
    C14 C1 C2 C3 . . . . -176.04(15) ?
    C1 C2 C3 C4 . . . . -0.8(3) ?
    C2 C3 C4 C5 . . . . 1.2(3) ?
    C3 C4 C5 C6 . . . . 0.1(3) ?
    C4 C5 C6 C1 . . . . -1.8(2) ?
    C4 C5 C6 C7 . . . . 173.23(15) ?
    C2 C1 C6 C5 . . . . 2.2(2) ?
    C14 C1 C6 C5 . . . . 177.49(14) ?
    C2 C1 C6 C7 . . . . -172.75(14) ?
    C14 C1 C6 C7 . . . . 2.6(2) ?
    C5 C6 C7 O1 . . . . 18.3(2) ?
    C1 C6 C7 O1 . . . . -166.66(15) ?
    C5 C6 C7 C8 . . . . -157.66(14) ?
    C1 C6 C7 C8 . . . . 17.4(2) ?
    O1 C7 C8 C13 . . . . 169.11(15) ?
    C6 C7 C8 C13 . . . . -14.9(2) ?
    O1 C7 C8 C9 . . . . -12.8(2) ?
    C6 C7 C8 C9 . . . . 163.10(15) ?
    C13 C8 C9 C10 . . . . 1.3(3) ?
    C7 C8 C9 C10 . . . . -176.73(16) ?
    C8 C9 C10 C11 . . . . 0.8(3) ?
    C9 C10 C11 C12 . . . . -1.6(3) ?
    C10 C11 C12 C13 . . . . 0.3(3) ?
    C9 C8 C13 C12 . . . . -2.5(2) ?
    C7 C8 C13 C12 . . . . 175.48(14) ?
    C9 C8 C13 C14 . . . . 174.59(15) ?
    C7 C8 C13 C14 . . . . -7.4(2) ?
    C11 C12 C13 C8 . . . . 1.7(2) ?
    C11 C12 C13 C14 . . . . -175.30(15) ?
    C8 C13 C14 C15 . . . . -150.02(15) ?
    C12 C13 C14 C15 . . . . 27.0(2) ?
    C8 C13 C14 C1 . . . . 27.30(19) ?
    C12 C13 C14 C1 . . . . -155.71(14) ?
    C2 C1 C14 C15 . . . . -32.6(2) ?
    C6 C1 C14 C15 . . . . 152.29(16) ?
    C2 C1 C14 C13 . . . . 150.25(14) ?
    C6 C1 C14 C13 . . . . -24.9(2) ?
    C13 C14 C15 C16 . . . . 169.27(16) ?
    C1 C14 C15 C16 . . . . -7.8(3) ?
    C14 C15 C16 C17 . . . . 142.24(19) ?
    C14 C15 C16 C21 . . . . -41.8(3) ?
    C21 C16 C17 C18 . . . . 2.4(2) ?
    C15 C16 C17 C18 . . . . 178.48(17) ?
    C16 C17 C18 C19 . . . . -1.5(3) ?
    C17 C18 C19 C20 . . . . -0.7(3) ?
    C17 C18 C19 C22 . . . . 179.07(18) ?
    C18 C19 C20 C21 . . . . 2.0(2) ?
    C22 C19 C20 C21 . . . . -177.81(17) ?
    C19 C20 C21 C16 . . . . -1.1(2) ?
    C17 C16 C21 C20 . . . . -1.1(2) ?
    C15 C16 C21 C20 . . . . -177.09(14) ?
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
    C3 H3A O1 2_655 0.95 2.35 3.275(2) 164 yes
    C22 H22C Cg1 2_555 0.98 2.94 3.726(2) 138 yes
    C17 H17A Cg2 4_555 0.95 2.76 3.5073(16) 136 yes
