##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# 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 2.1.    #
#                                                                            #
# 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     SHELXL97
_journal_date_recd_electronic     2007-10-13
_journal_date_accepted     2007-10-25
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2007
_journal_volume     63
_journal_issue     12
_journal_page_first     o4530
_journal_page_last     o4530
_journal_paper_category     QO
_journal_coeditor_code     IS2223
_publ_contact_author_name     'V.Manivannan'
_publ_contact_author_address
;
Department of Physics
Presidency College
Chennai 600 005
India
;
_publ_contact_author_email     manivan_1999@yahoo.com
_publ_contact_author_fax     ?
_publ_contact_author_phone     '04426187785'
_publ_section_title
;
3-Benzylidene-8-methoxy-6-methylchroman-4-one
;
loop_
    _publ_author_name
    _publ_author_address
    'A. Marx'
;
Department of Physics
Presidency College
Chennai 600 005
India
;
    'R. Suresh'
;
Department of Chemistry
Presidency College
Chennai 600 005
India
;
    'Charles Christoper Kanagam'
;
Department of Chemistry
Valliammai Engineering College
Kattankulathur
Chennai
India
;
    'V. Manivannan'
;
Department of Physics
Presidency College
Chennai 600 005
India
;
    'Büyükgüngör, Orhan'
;
Department of Physics
Ondokuz Mayis University
TR-55139 Samsun
Turkey
;
data_I
_chemical_name_systematic
;
3-Benzylidene-8-methoxy-6-methylchroman-4-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C18 H16 O3'
_chemical_formula_sum     'C18 H16 O3'
_chemical_formula_iupac     'C18 H16 O3'
_chemical_formula_weight     280.31
_chemical_melting_point     ?
_symmetry_cell_setting     'monoclinic'
_symmetry_space_group_name_H-M     'P 21/a'
_symmetry_space_group_name_Hall     '-P 2yab'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z'
_cell_length_a     13.0081(9)
_cell_length_b     8.1407(5)
_cell_length_c     13.7580(10)
_cell_angle_alpha     90.00
_cell_angle_beta     107.522(5)
_cell_angle_gamma     90.00
_cell_volume     1389.31(16)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     20682
_cell_measurement_theta_min     1.64
_cell_measurement_theta_max     28.83
_cell_measurement_temperature     150(2)
_exptl_crystal_description     'plate'
_exptl_crystal_colour     'yellow'
_exptl_crystal_size_max     0.440
_exptl_crystal_size_mid     0.287
_exptl_crystal_size_min     0.060
_exptl_crystal_density_diffrn     1.340
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     592
_exptl_absorpt_coefficient_mu     0.091
_exptl_absorpt_correction_type     integration
_exptl_absorpt_process_details     '(X-RED; Stoe & Cie, 2002)'
_exptl_absorpt_correction_T_min     0.988
_exptl_absorpt_correction_T_max     0.991
_exptl_special_details
;
;
_diffrn_ambient_temperature     150(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     'Stoe IPDS2'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     6.67
_diffrn_reflns_number     15939
_diffrn_reflns_av_R_equivalents     0.0552
_diffrn_reflns_av_sigmaI/netI     0.0383
_diffrn_reflns_theta_min     2.94
_diffrn_reflns_theta_max     28.70
_diffrn_reflns_theta_full     28.70
_diffrn_measured_fraction_theta_max     0.990
_diffrn_measured_fraction_theta_full     0.990
_diffrn_reflns_limit_h_min     -17
_diffrn_reflns_limit_h_max     17
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_l_min     -18
_diffrn_reflns_limit_l_max     18
_diffrn_standards_number     ?
_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     3551
_reflns_number_gt     2574
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0604
_refine_ls_R_factor_gt     0.0387
_refine_ls_wR_factor_gt     0.0924
_refine_ls_wR_factor_ref     0.0991
_refine_ls_goodness_of_fit_ref     1.027
_refine_ls_restrained_S_all     1.027
_refine_ls_number_reflns     3551
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
          'calc w=1/[σ²(Fo²)+(0.0515P)²+0.065P] 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     0.215
_refine_diff_density_min     -0.152
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection     'X-AREA (Stoe & Cie, 2002)'
_computing_cell_refinement     'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction     'X-RED32 (Stoe & Cie, 2002)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'PLATON (Spek, 2003)'
_computing_publication_material     'SHELXL97 (Sheldrick, 1997)'
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
    O O1 0.78602(7) 0.02990(10) 0.02502(6) 0.0269(2) Uani d . 1 . .
    O O3 0.75897(7) 0.05559(10) -0.17011(7) 0.0281(2) Uani d . 1 . .
    O O2 1.02517(7) -0.25015(11) 0.21383(7) 0.0316(2) Uani d . 1 . .
    C C17 0.89940(10) -0.14732(14) -0.16166(9) 0.0259(3) Uani d . 1 . .
    H H17 0.8907 -0.1371 -0.2325 0.031 Uiso calc R 1 . .
    C C11 0.92597(9) -0.17538(14) 0.04513(9) 0.0240(2) Uani d . 1 . .
    C C13 0.83512(10) -0.05403(14) -0.11889(9) 0.0243(2) Uani d . 1 . .
    C C10 0.84867(9) -0.06858(13) -0.01381(9) 0.0234(2) Uani d . 1 . .
    C C8 0.87402(10) -0.07504(14) 0.19619(9) 0.0249(2) Uani d . 1 . .
    C C14 0.73210(12) 0.05403(17) -0.27867(10) 0.0349(3) Uani d . 1 . .
    H H14A 0.7934 0.0950 -0.2991 0.052 Uiso calc R 1 . .
    H H14B 0.6693 0.1246 -0.3078 0.052 Uiso calc R 1 . .
    H H14C 0.7152 -0.0585 -0.3036 0.052 Uiso calc R 1 . .
    C C16 0.97710(10) -0.25671(14) -0.10298(10) 0.0263(3) Uani d . 1 . .
    C C12 0.94866(10) -0.17583(14) 0.15659(9) 0.0249(2) Uani d . 1 . .
    C C1 0.84397(10) 0.05118(15) 0.35372(9) 0.0273(3) Uani d . 1 . .
    C C7 0.90426(10) -0.03749(15) 0.29547(10) 0.0271(3) Uani d . 1 . .
    H H7 0.9744 -0.0731 0.3335 0.033 Uiso calc R 1 . .
    C C15 0.98897(10) -0.27015(14) -0.00074(10) 0.0262(3) Uani d . 1 . .
    H H15 1.0406 -0.3447 0.0397 0.031 Uiso calc R 1 . .
    C C6 0.73213(11) 0.03713(16) 0.33350(10) 0.0301(3) Uani d . 1 . .
    H H6 0.6917 -0.0300 0.2788 0.036 Uiso calc R 1 . .
    C C2 0.90143(12) 0.14728(16) 0.43647(10) 0.0332(3) Uani d . 1 . .
    H H2 0.9776 0.1551 0.4527 0.040 Uiso calc R 1 . .
    C C9 0.77010(10) -0.02889(16) 0.11825(10) 0.0276(3) Uani d . 1 . .
    H H9A 0.7220 -0.1259 0.1030 0.033 Uiso calc R 1 . .
    H H9B 0.7341 0.0576 0.1467 0.033 Uiso calc R 1 . .
    C C4 0.73819(13) 0.21907(18) 0.47312(11) 0.0389(3) Uani d . 1 . .
    H H4 0.7020 0.2778 0.5128 0.047 Uiso calc R 1 . .
    C C5 0.68008(12) 0.12118(18) 0.39318(10) 0.0350(3) Uani d . 1 . .
    H H5 0.6042 0.1113 0.3790 0.042 Uiso calc R 1 . .
    C C18 1.04741(11) -0.35413(16) -0.15150(11) 0.0329(3) Uani d . 1 . .
    H H18A 1.1090 -0.3991 -0.0982 0.049 Uiso calc R 1 . .
    H H18B 1.0734 -0.2823 -0.1962 0.049 Uiso calc R 1 . .
    H H18C 1.0054 -0.4443 -0.1916 0.049 Uiso calc R 1 . .
    C C3 0.84876(13) 0.23136(18) 0.49522(11) 0.0393(3) Uani d . 1 . .
    H H3 0.8888 0.2974 0.5507 0.047 Uiso calc R 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
    O1 0.0305(5) 0.0265(4) 0.0239(4) 0.0063(3) 0.0085(4) 0.0005(3)
    O3 0.0337(5) 0.0253(4) 0.0241(4) 0.0048(4) 0.0071(4) 0.0018(3)
    O2 0.0315(5) 0.0287(4) 0.0308(5) 0.0055(4) 0.0038(4) 0.0012(4)
    C17 0.0287(6) 0.0230(5) 0.0265(6) -0.0041(5) 0.0090(5) -0.0040(4)
    C11 0.0241(6) 0.0195(5) 0.0273(6) -0.0023(4) 0.0063(5) -0.0013(4)
    C13 0.0261(6) 0.0189(5) 0.0267(6) -0.0016(4) 0.0062(5) -0.0004(4)
    C10 0.0247(6) 0.0188(5) 0.0269(6) -0.0017(4) 0.0080(5) -0.0030(4)
    C8 0.0264(6) 0.0208(5) 0.0274(6) -0.0010(4) 0.0080(5) 0.0011(4)
    C14 0.0438(8) 0.0331(7) 0.0247(7) 0.0067(6) 0.0057(6) 0.0003(5)
    C16 0.0261(6) 0.0206(5) 0.0329(7) -0.0036(5) 0.0098(5) -0.0057(5)
    C12 0.0251(6) 0.0205(5) 0.0271(6) -0.0012(4) 0.0048(5) 0.0000(4)
    C1 0.0353(7) 0.0238(6) 0.0221(6) 0.0022(5) 0.0076(5) 0.0037(5)
    C7 0.0289(6) 0.0240(6) 0.0269(6) -0.0001(5) 0.0061(5) 0.0017(5)
    C15 0.0240(6) 0.0201(5) 0.0329(7) -0.0004(4) 0.0063(5) -0.0015(5)
    C6 0.0373(7) 0.0289(6) 0.0241(6) 0.0014(5) 0.0094(5) 0.0038(5)
    C2 0.0377(7) 0.0311(7) 0.0275(7) 0.0031(5) 0.0048(5) 0.0001(5)
    C9 0.0278(6) 0.0303(6) 0.0254(6) 0.0030(5) 0.0089(5) 0.0012(5)
    C4 0.0536(9) 0.0375(7) 0.0278(7) 0.0134(6) 0.0155(7) 0.0021(6)
    C5 0.0402(8) 0.0383(7) 0.0285(7) 0.0076(6) 0.0134(6) 0.0069(6)
    C18 0.0351(7) 0.0285(6) 0.0371(7) 0.0025(5) 0.0139(6) -0.0052(5)
    C3 0.0529(9) 0.0349(7) 0.0256(7) 0.0066(6) 0.0052(6) -0.0048(5)
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds 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 C10 . 1.3617(14) n
    O1 C9 . 1.4412(15) n
    O3 C13 . 1.3615(14) n
    O3 C14 . 1.4280(15) n
    O2 C12 . 1.2268(15) n
    C17 C13 . 1.3851(16) ?
    C17 C16 . 1.4054(18) ?
    C17 H17 . 0.9500 ?
    C11 C10 . 1.3906(16) ?
    C11 C15 . 1.4058(16) ?
    C11 C12 . 1.4718(17) ?
    C13 C10 . 1.4076(17) ?
    C8 C7 . 1.3381(18) ?
    C8 C12 . 1.4937(16) ?
    C8 C9 . 1.4985(18) ?
    C14 H14A . 0.9800 ?
    C14 H14B . 0.9800 ?
    C14 H14C . 0.9800 ?
    C16 C15 . 1.3724(18) ?
    C16 C18 . 1.5095(17) ?
    C1 C2 . 1.3981(18) ?
    C1 C6 . 1.4012(18) ?
    C1 C7 . 1.4685(17) ?
    C7 H7 . 0.9500 ?
    C15 H15 . 0.9500 ?
    C6 C5 . 1.3913(18) ?
    C6 H6 . 0.9500 ?
    C2 C3 . 1.3873(19) ?
    C2 H2 . 0.9500 ?
    C9 H9A . 0.9900 ?
    C9 H9B . 0.9900 ?
    C4 C3 . 1.381(2) ?
    C4 C5 . 1.384(2) ?
    C4 H4 . 0.9500 ?
    C5 H5 . 0.9500 ?
    C18 H18A . 0.9800 ?
    C18 H18B . 0.9800 ?
    C18 H18C . 0.9800 ?
    C3 H3 . 0.9500 ?
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
    C10 O1 C9 . . 114.64(9) n
    C13 O3 C14 . . 116.51(9) n
    C13 C17 C16 . . 121.68(11) ?
    C13 C17 H17 . . 119.2 ?
    C16 C17 H17 . . 119.2 ?
    C10 C11 C15 . . 119.89(11) ?
    C10 C11 C12 . . 119.48(10) ?
    C15 C11 C12 . . 120.35(11) ?
    O3 C13 C17 . . 125.28(11) n
    O3 C13 C10 . . 115.68(10) n
    C17 C13 C10 . . 119.03(11) ?
    O1 C10 C11 . . 123.53(11) n
    O1 C10 C13 . . 116.66(10) n
    C11 C10 C13 . . 119.76(10) ?
    C7 C8 C12 . . 118.31(11) ?
    C7 C8 C9 . . 126.72(11) ?
    C12 C8 C9 . . 114.97(10) ?
    O3 C14 H14A . . 109.5 ?
    O3 C14 H14B . . 109.5 ?
    H14A C14 H14B . . 109.5 ?
    O3 C14 H14C . . 109.5 ?
    H14A C14 H14C . . 109.5 ?
    H14B C14 H14C . . 109.5 ?
    C15 C16 C17 . . 118.60(11) ?
    C15 C16 C18 . . 121.01(12) ?
    C17 C16 C18 . . 120.37(11) ?
    O2 C12 C11 . . 122.65(11) n
    O2 C12 C8 . . 121.84(11) n
    C11 C12 C8 . . 115.48(10) ?
    C2 C1 C6 . . 118.42(12) ?
    C2 C1 C7 . . 118.49(12) ?
    C6 C1 C7 . . 123.00(12) ?
    C8 C7 C1 . . 128.91(12) ?
    C8 C7 H7 . . 115.5 ?
    C1 C7 H7 . . 115.5 ?
    C16 C15 C11 . . 121.03(11) ?
    C16 C15 H15 . . 119.5 ?
    C11 C15 H15 . . 119.5 ?
    C5 C6 C1 . . 120.22(13) ?
    C5 C6 H6 . . 119.9 ?
    C1 C6 H6 . . 119.9 ?
    C3 C2 C1 . . 120.92(13) ?
    C3 C2 H2 . . 119.5 ?
    C1 C2 H2 . . 119.5 ?
    O1 C9 C8 . . 112.32(10) n
    O1 C9 H9A . . 109.1 ?
    C8 C9 H9A . . 109.1 ?
    O1 C9 H9B . . 109.1 ?
    C8 C9 H9B . . 109.1 ?
    H9A C9 H9B . . 107.9 ?
    C3 C4 C5 . . 120.00(13) ?
    C3 C4 H4 . . 120.0 ?
    C5 C4 H4 . . 120.0 ?
    C4 C5 C6 . . 120.39(14) ?
    C4 C5 H5 . . 119.8 ?
    C6 C5 H5 . . 119.8 ?
    C16 C18 H18A . . 109.5 ?
    C16 C18 H18B . . 109.5 ?
    H18A C18 H18B . . 109.5 ?
    C16 C18 H18C . . 109.5 ?
    H18A C18 H18C . . 109.5 ?
    H18B C18 H18C . . 109.5 ?
    C4 C3 C2 . . 120.01(13) ?
    C4 C3 H3 . . 120.0 ?
    C2 C3 H3 . . 120.0 ?
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 H7 O2 . 0.95 2.43 2.7922(15) 103
    C18 H18C O2 3_745 0.98 2.52 3.3937(16) 148
    C9 H9B Cg1 2_655 0.99 2.99 3.7499(14) 135
    C14 H14C Cg2 2_645 0.98 2.91 3.8592(15) 162
