##############################################################################
#                                                                            #
# 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     2012-07-31
_journal_date_accepted     2012-08-07
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2012
_journal_volume     68
_journal_issue      9
_journal_page_first     o2724
_journal_page_last     o2724
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536812034897
_journal_coeditor_code     IS5181
_publ_contact_author_name     'Prof. Fun, Hoong-Kun'
_publ_contact_author_address
;
      X-ray Crystallography Unit
      School of Physics
      Universiti Sains Malaysia
      11800 USM, Penang
      MALAYSIA
;
_publ_contact_author_email     'hkfun@usm.my'
_publ_contact_author_fax     '604 6579150'
_publ_contact_author_phone     '604 6533652'
_publ_section_title
;
(2E)-3-[4-(Benzyloxy)phenyl]-1-(pyridin-3-yl)prop-2-en-1-one
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Hoong-Kun Fun'
;
      Thomson Reuters ResearcherID: A-3561-2009.
;
;     X-ray Crystallography Unit
      School of Physics
      Universiti Sains Malaysia
      11800 USM, Penang
      Malaysia
;
    'Ching Kheng Quah'
;
      Thomson Reuters ResearcherID: A-5525-2009.
;
;
      X-ray Crystallography Unit
      School of Physics
      Universiti Sains Malaysia
      11800 USM, Penang
      Malaysia
;
    'Prakash S. Nayak' ?
;
      Department of Studies in Chemistry
      Mangalore University
      Mangalagangotri 574 199
      India
;
    'B. Narayana' ?
;
      Department of Studies in Chemistry
      Mangalore University
      Mangalagangotri 574 199
      India
;
    'B. K. Sarojini' ?
;
      Department of Chemistry
      P. A. College of Engineering
      Nadupadavu, Mangalore 574 153
      India
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
(2E)-3-[4-(Benzyloxy)phenyl]-1-(pyridin-3-yl)prop-2-en-1-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C21 H17 N O2'
_chemical_formula_sum     'C21 H17 N O2'
_chemical_formula_iupac     'C21 H17 N O2'
_chemical_formula_weight     315.36
_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     5.9845(6)
_cell_length_b     38.187(4)
_cell_length_c     8.5412(7)
_cell_angle_alpha     90.00
_cell_angle_beta     123.372(5)
_cell_angle_gamma     90.00
_cell_volume     1630.1(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     4372
_cell_measurement_theta_min     2.86
_cell_measurement_theta_max     26.53
_cell_measurement_temperature     100
_exptl_crystal_description     'block'
_exptl_crystal_colour     'yellow'
_exptl_crystal_size_max     0.401
_exptl_crystal_size_mid     0.33
_exptl_crystal_size_min     0.166
_exptl_crystal_density_diffrn     1.285
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     664
_exptl_absorpt_coefficient_mu     0.083
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2009)'
_exptl_absorpt_correction_T_min     0.9676
_exptl_absorpt_correction_T_max     0.9864
_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
_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 DUO CCD area-detector
;
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     18812
_diffrn_reflns_av_R_equivalents     0.0283
_diffrn_reflns_av_sigmaI/netI     0.0266
_diffrn_reflns_theta_min     2.13
_diffrn_reflns_theta_max     30.02
_diffrn_reflns_theta_full     30.02
_diffrn_measured_fraction_theta_max     0.996
_diffrn_measured_fraction_theta_full     0.996
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     -53
_diffrn_reflns_limit_k_max     47
_diffrn_reflns_limit_l_min     -11
_diffrn_reflns_limit_l_max     11
_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     4751
_reflns_number_gt     3171
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0786
_refine_ls_R_factor_gt     0.0495
_refine_ls_wR_factor_gt     0.1240
_refine_ls_wR_factor_ref     0.1410
_refine_ls_goodness_of_fit_ref     1.024
_refine_ls_restrained_S_all     1.024
_refine_ls_number_reflns     4751
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0590P)²+0.2532P] 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     0.001
_refine_diff_density_max     0.166
_refine_diff_density_min     -0.153
_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'
    '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'
_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 -0.1642(2) -0.12817(2) 0.76557(15) 0.0534(3) Uani d . 1 1 . .
    O O2 0.6625(3) 0.04322(3) 0.69065(19) 0.0690(3) Uani d . 1 1 . .
    N N1 0.5921(3) 0.14650(3) 0.7813(2) 0.0668(4) Uani d . 1 1 . .
    C C1 -0.2000(4) -0.20724(4) 0.8950(3) 0.0637(4) Uani d . 1 1 . .
    H H1A -0.0178 -0.2048 0.9949 0.076 Uiso calc R 1 1 . .
    C C2 -0.3631(4) -0.23073(4) 0.9115(3) 0.0725(5) Uani d . 1 1 . .
    H H2A -0.2924 -0.2442 1.0225 0.087 Uiso calc R 1 1 . .
    C C3 -0.6271(4) -0.23442(4) 0.7671(3) 0.0700(5) Uani d . 1 1 . .
    H H3A -0.7382 -0.2506 0.7778 0.084 Uiso calc R 1 1 . .
    C C4 -0.7299(4) -0.21464(4) 0.6074(3) 0.0673(4) Uani d . 1 1 . .
    H H4A -0.9128 -0.2169 0.5085 0.081 Uiso calc R 1 1 . .
    C C5 -0.5668(3) -0.19132(4) 0.5905(2) 0.0583(4) Uani d . 1 1 . .
    H H5A -0.6381 -0.1779 0.4792 0.070 Uiso calc R 1 1 . .
    C C6 -0.3010(3) -0.18749(3) 0.7344(2) 0.0496(3) Uani d . 1 1 . .
    C C7 -0.1254(3) -0.16226(3) 0.7147(2) 0.0524(3) Uani d . 1 1 . .
    H H7A 0.0645 -0.1693 0.7978 0.063 Uiso calc R 1 1 . .
    H H7B -0.1734 -0.1621 0.5838 0.063 Uiso calc R 1 1 . .
    C C8 -0.0323(3) -0.10096(3) 0.74586(18) 0.0425(3) Uani d . 1 1 . .
    C C9 -0.0638(3) -0.06836(3) 0.8049(2) 0.0480(3) Uani d . 1 1 . .
    H H9A -0.1686 -0.0664 0.8569 0.058 Uiso calc R 1 1 . .
    C C10 0.0551(3) -0.03911(3) 0.7886(2) 0.0467(3) Uani d . 1 1 . .
    H H10A 0.0300 -0.0170 0.8282 0.056 Uiso calc R 1 1 . .
    C C11 0.2133(2) -0.04140(3) 0.71422(18) 0.0427(3) Uani d . 1 1 . .
    C C12 0.2424(3) -0.07406(3) 0.65656(19) 0.0485(3) Uani d . 1 1 . .
    H H12A 0.3472 -0.0761 0.6045 0.058 Uiso calc R 1 1 . .
    C C13 0.1238(3) -0.10387(4) 0.6723(2) 0.0484(3) Uani d . 1 1 . .
    H H13A 0.1490 -0.1260 0.6332 0.058 Uiso calc R 1 1 . .
    C C14 0.3499(3) -0.01114(3) 0.69900(19) 0.0467(3) Uani d . 1 1 . .
    H H14A 0.4507 -0.0153 0.6454 0.056 Uiso calc R 1 1 . .
    C C15 0.3490(3) 0.02140(4) 0.7514(2) 0.0507(3) Uani d . 1 1 . .
    H H15A 0.2462 0.0269 0.8021 0.061 Uiso calc R 1 1 . .
    C C16 0.5021(3) 0.04934(4) 0.73355(19) 0.0470(3) Uani d . 1 1 . .
    C C17 0.4655(3) 0.08627(3) 0.77386(18) 0.0433(3) Uani d . 1 1 . .
    C C18 0.6038(3) 0.11266(4) 0.7499(2) 0.0562(4) Uani d . 1 1 . .
    H H18A 0.7154 0.1060 0.7079 0.067 Uiso calc R 1 1 . .
    C C19 0.4329(4) 0.15510(4) 0.8397(2) 0.0652(4) Uani d . 1 1 . .
    H H19A 0.4199 0.1791 0.8629 0.078 Uiso calc R 1 1 . .
    C C20 0.2878(4) 0.13133(4) 0.8679(3) 0.0687(5) Uani d . 1 1 . .
    H H20A 0.1783 0.1388 0.9103 0.082 Uiso calc R 1 1 . .
    C C21 0.3026(3) 0.09635(4) 0.8339(2) 0.0579(4) Uani d . 1 1 . .
    H H21A 0.2022 0.0794 0.8516 0.069 Uiso calc R 1 1 . .
_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 C8 . 1.3700(15) ?
    O1 C7 . 1.4313(15) ?
    O2 C16 . 1.2235(16) ?
    N1 C18 . 1.3297(19) ?
    N1 C19 . 1.337(2) ?
    C1 C6 . 1.380(2) ?
    C1 C2 . 1.388(2) ?
    C1 H1A . 0.9500 ?
    C2 C3 . 1.376(3) ?
    C2 H2A . 0.9500 ?
    C3 C4 . 1.373(3) ?
    C3 H3A . 0.9500 ?
    C4 C5 . 1.386(2) ?
    C4 H4A . 0.9500 ?
    C5 C6 . 1.383(2) ?
    C5 H5A . 0.9500 ?
    C6 C7 . 1.5019(18) ?
    C7 H7A . 0.9900 ?
    C7 H7B . 0.9900 ?
    C8 C13 . 1.3877(18) ?
    C8 C9 . 1.3943(18) ?
    C9 C10 . 1.3718(18) ?
    C9 H9A . 0.9500 ?
    C10 C11 . 1.4037(18) ?
    C10 H10A . 0.9500 ?
    C11 C12 . 1.3869(18) ?
    C11 C14 . 1.4620(17) ?
    C12 C13 . 1.3866(18) ?
    C12 H12A . 0.9500 ?
    C13 H13A . 0.9500 ?
    C14 C15 . 1.3217(19) ?
    C14 H14A . 0.9500 ?
    C15 C16 . 1.4682(18) ?
    C15 H15A . 0.9500 ?
    C16 C17 . 1.4963(18) ?
    C17 C21 . 1.3826(19) ?
    C17 C18 . 1.3889(18) ?
    C18 H18A . 0.9500 ?
    C19 C20 . 1.366(2) ?
    C19 H19A . 0.9500 ?
    C20 C21 . 1.380(2) ?
    C20 H20A . 0.9500 ?
    C21 H21A . 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
    C8 O1 C7 . . 116.85(10) ?
    C18 N1 C19 . . 116.22(13) ?
    C6 C1 C2 . . 120.41(17) ?
    C6 C1 H1A . . 119.8 ?
    C2 C1 H1A . . 119.8 ?
    C3 C2 C1 . . 119.97(16) ?
    C3 C2 H2A . . 120.0 ?
    C1 C2 H2A . . 120.0 ?
    C4 C3 C2 . . 120.02(15) ?
    C4 C3 H3A . . 120.0 ?
    C2 C3 H3A . . 120.0 ?
    C3 C4 C5 . . 120.03(17) ?
    C3 C4 H4A . . 120.0 ?
    C5 C4 H4A . . 120.0 ?
    C6 C5 C4 . . 120.44(16) ?
    C6 C5 H5A . . 119.8 ?
    C4 C5 H5A . . 119.8 ?
    C1 C6 C5 . . 119.13(14) ?
    C1 C6 C7 . . 120.75(14) ?
    C5 C6 C7 . . 120.12(13) ?
    O1 C7 C6 . . 108.00(11) ?
    O1 C7 H7A . . 110.1 ?
    C6 C7 H7A . . 110.1 ?
    O1 C7 H7B . . 110.1 ?
    C6 C7 H7B . . 110.1 ?
    H7A C7 H7B . . 108.4 ?
    O1 C8 C13 . . 124.89(11) ?
    O1 C8 C9 . . 115.53(11) ?
    C13 C8 C9 . . 119.58(12) ?
    C10 C9 C8 . . 120.64(12) ?
    C10 C9 H9A . . 119.7 ?
    C8 C9 H9A . . 119.7 ?
    C9 C10 C11 . . 120.79(12) ?
    C9 C10 H10A . . 119.6 ?
    C11 C10 H10A . . 119.6 ?
    C12 C11 C10 . . 117.68(11) ?
    C12 C11 C14 . . 119.58(12) ?
    C10 C11 C14 . . 122.73(12) ?
    C13 C12 C11 . . 122.20(12) ?
    C13 C12 H12A . . 118.9 ?
    C11 C12 H12A . . 118.9 ?
    C12 C13 C8 . . 119.10(12) ?
    C12 C13 H13A . . 120.4 ?
    C8 C13 H13A . . 120.4 ?
    C15 C14 C11 . . 127.31(12) ?
    C15 C14 H14A . . 116.3 ?
    C11 C14 H14A . . 116.3 ?
    C14 C15 C16 . . 121.93(13) ?
    C14 C15 H15A . . 119.0 ?
    C16 C15 H15A . . 119.0 ?
    O2 C16 C15 . . 121.97(13) ?
    O2 C16 C17 . . 119.18(12) ?
    C15 C16 C17 . . 118.83(11) ?
    C21 C17 C18 . . 116.88(13) ?
    C21 C17 C16 . . 124.77(12) ?
    C18 C17 C16 . . 118.36(11) ?
    N1 C18 C17 . . 124.98(14) ?
    N1 C18 H18A . . 117.5 ?
    C17 C18 H18A . . 117.5 ?
    N1 C19 C20 . . 123.70(15) ?
    N1 C19 H19A . . 118.2 ?
    C20 C19 H19A . . 118.2 ?
    C19 C20 C21 . . 119.08(15) ?
    C19 C20 H20A . . 120.5 ?
    C21 C20 H20A . . 120.5 ?
    C20 C21 C17 . . 119.14(14) ?
    C20 C21 H21A . . 120.4 ?
    C17 C21 H21A . . 120.4 ?
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 . . . . 0.0(3) ?
    C1 C2 C3 C4 . . . . -0.6(3) ?
    C2 C3 C4 C5 . . . . 0.9(3) ?
    C3 C4 C5 C6 . . . . -0.7(2) ?
    C2 C1 C6 C5 . . . . 0.2(2) ?
    C2 C1 C6 C7 . . . . -179.44(14) ?
    C4 C5 C6 C1 . . . . 0.1(2) ?
    C4 C5 C6 C7 . . . . 179.77(13) ?
    C8 O1 C7 C6 . . . . -176.20(12) ?
    C1 C6 C7 O1 . . . . -96.55(15) ?
    C5 C6 C7 O1 . . . . 83.83(16) ?
    C7 O1 C8 C13 . . . . 3.3(2) ?
    C7 O1 C8 C9 . . . . -177.05(12) ?
    O1 C8 C9 C10 . . . . -178.79(12) ?
    C13 C8 C9 C10 . . . . 0.9(2) ?
    C8 C9 C10 C11 . . . . -0.7(2) ?
    C9 C10 C11 C12 . . . . 0.6(2) ?
    C9 C10 C11 C14 . . . . -178.24(13) ?
    C10 C11 C12 C13 . . . . -0.7(2) ?
    C14 C11 C12 C13 . . . . 178.21(13) ?
    C11 C12 C13 C8 . . . . 0.9(2) ?
    O1 C8 C13 C12 . . . . 178.71(12) ?
    C9 C8 C13 C12 . . . . -0.9(2) ?
    C12 C11 C14 C15 . . . . -178.19(14) ?
    C10 C11 C14 C15 . . . . 0.7(2) ?
    C11 C14 C15 C16 . . . . 178.09(13) ?
    C14 C15 C16 O2 . . . . -8.9(2) ?
    C14 C15 C16 C17 . . . . 172.68(13) ?
    O2 C16 C17 C21 . . . . -176.13(15) ?
    C15 C16 C17 C21 . . . . 2.4(2) ?
    O2 C16 C17 C18 . . . . 3.9(2) ?
    C15 C16 C17 C18 . . . . -177.67(13) ?
    C19 N1 C18 C17 . . . . -0.2(3) ?
    C21 C17 C18 N1 . . . . 0.4(2) ?
    C16 C17 C18 N1 . . . . -179.58(15) ?
    C18 N1 C19 C20 . . . . 0.2(3) ?
    N1 C19 C20 C21 . . . . -0.4(3) ?
    C19 C20 C21 C17 . . . . 0.5(3) ?
    C18 C17 C21 C20 . . . . -0.5(2) ?
    C16 C17 C21 C20 . . . . 179.44(15) ?
