#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/28/2222878.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2222878
loop_
_publ_author_name
'Jasinski, Jerry P.'
'Butcher, Ray J.'
'Veena, K.'
'Narayana, B.'
'Yathirajan, H. S.'
_publ_section_title
;
 A second polymorph of
 (2E)-1-(4-fluorophenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one
;
_journal_coeditor_code           SJ2632
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1965
_journal_page_last               o1966
_journal_paper_doi               10.1107/S1600536809028517
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C18 H17 F O4'
_chemical_formula_moiety         'C18 H17 F O4'
_chemical_formula_sum            'C18 H17 F O4'
_chemical_formula_weight         316.32
_chemical_name_systematic
;
(2E)-1-(4-fluorophenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 98.3217(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.4250(2)
_cell_length_b                   8.62800(10)
_cell_length_c                   14.9038(2)
_cell_measurement_reflns_used    4493
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      77.2678
_cell_measurement_theta_min      4.3281
_cell_volume                     1580.91(4)
_computing_cell_refinement
'CrysAlis RED (Oxford Diffraction, 2007)'
_computing_data_collection
'CrysAlis Pro (Oxford Diffraction, 2007)'
_computing_data_reduction
'CrysAlis RED (Oxford Diffraction, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 10.5081
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device_type  'Oxford Diffraction Gemini R'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0181
_diffrn_reflns_av_sigmaI/netI    0.0158
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8137
_diffrn_reflns_theta_full        67.50
_diffrn_reflns_theta_max         77.89
_diffrn_reflns_theta_min         5.94
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.846
_exptl_absorpt_correction_T_max  0.830
_exptl_absorpt_correction_T_min  0.557
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis RED; Oxford Diffraction, 2007)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.126
_refine_diff_density_min         -0.176
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3216
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0402
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0683P)²+0.1035P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1171
_refine_ls_wR_factor_ref         0.1260
_reflns_number_gt                2396
_reflns_number_total             3216
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj2632.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2222878
_cod_database_fobs_code          2222878
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'
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 O4 0.54332(9) 0.78663(17) 0.56646(8) 0.0813(4) Uani d . 1 . .
F F 0.12194(11) 0.38071(16) -0.04098(8) 0.0982(4) Uani d . 1 . .
O O1 0.01131(9) 0.41222(15) 0.35678(8) 0.0737(3) Uani d . 1 . .
O O2 0.33800(9) 0.64264(16) 0.79007(7) 0.0751(3) Uani d . 1 . .
O O3 0.51516(9) 0.76879(15) 0.74012(8) 0.0716(3) Uani d . 1 . .
C C1 0.10184(11) 0.43862(16) 0.22896(11) 0.0576(3) Uani d . 1 . .
C C2 0.16144(13) 0.54012(19) 0.18363(12) 0.0684(4) Uani d . 1 . .
H H2A 0.1980 0.6219 0.2152 0.082 Uiso calc R 1 . .
C C3 0.16769(15) 0.5225(2) 0.09261(12) 0.0745(4) Uani d . 1 . .
H H3A 0.2071 0.5920 0.0625 0.089 Uiso calc R 1 . .
C C4 0.11452(13) 0.4002(2) 0.04776(12) 0.0698(4) Uani d . 1 . .
C C5 0.05441(14) 0.2970(2) 0.08954(14) 0.0765(5) Uani d . 1 . .
H H5A 0.0189 0.2149 0.0574 0.092 Uiso calc R 1 . .
C C6 0.04768(13) 0.31760(19) 0.17996(13) 0.0695(4) Uani d . 1 . .
H H6A 0.0061 0.2493 0.2090 0.083 Uiso calc R 1 . .
C C7 0.09279(11) 0.45582(16) 0.32705(11) 0.0591(3) Uani d . 1 . .
C C8 0.18590(12) 0.52523(19) 0.38636(11) 0.0633(4) Uani d . 1 . .
H H8A 0.2441 0.5643 0.3605 0.076 Uiso calc R 1 . .
C C9 0.18866(11) 0.53327(18) 0.47527(11) 0.0612(4) Uani d . 1 . .
H H9A 0.1275 0.4964 0.4978 0.073 Uiso calc R 1 . .
C C10 0.27643(11) 0.59319(17) 0.54241(10) 0.0572(3) Uani d . 1 . .
C C11 0.26418(11) 0.58419(18) 0.63367(10) 0.0605(4) Uani d . 1 . .
H H11A 0.2019 0.5398 0.6505 0.073 Uiso calc R 1 . .
C C12 0.34453(11) 0.64123(18) 0.69953(10) 0.0587(3) Uani d . 1 . .
C C13 0.43756(12) 0.70811(18) 0.67455(10) 0.0591(3) Uani d . 1 . .
C C14 0.44971(11) 0.71778(19) 0.58304(10) 0.0611(4) Uani d . 1 . .
C C15 0.36992(12) 0.66065(19) 0.51690(10) 0.0611(4) Uani d . 1 . .
H H15A 0.3783 0.6670 0.4560 0.073 Uiso calc R 1 . .
C C16 0.25626(17) 0.5508(3) 0.82150(13) 0.0855(5) Uani d . 1 . .
H H16A 0.1858 0.5875 0.7950 0.128 Uiso calc R 1 . .
H H16B 0.2630 0.5581 0.8863 0.128 Uiso calc R 1 . .
H H16C 0.2647 0.4448 0.8044 0.128 Uiso calc R 1 . .
C C17 0.60831(14) 0.6733(3) 0.75995(13) 0.0836(5) Uani d . 1 . .
H H17A 0.5874 0.5746 0.7817 0.125 Uiso calc R 1 . .
H H17B 0.6597 0.7219 0.8056 0.125 Uiso calc R 1 . .
H H17C 0.6410 0.6586 0.7060 0.125 Uiso calc R 1 . .
C C18 0.56292(15) 0.7943(3) 0.47481(13) 0.0864(6) Uani d . 1 . .
H H18A 0.5608 0.6918 0.4496 0.130 Uiso calc R 1 . .
H H18B 0.6332 0.8392 0.4727 0.130 Uiso calc R 1 . .
H H18C 0.5080 0.8571 0.4403 0.130 Uiso calc R 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
C14 O4 C18 . . 117.66(13) ?
C12 O2 C16 . . 117.99(14) ?
C13 O3 C17 . . 113.25(13) ?
C2 C1 C6 . . 118.10(15) ?
C2 C1 C7 . . 122.51(13) ?
C6 C1 C7 . . 119.38(13) ?
C3 C2 C1 . . 121.37(15) ?
C3 C2 H2A . . 119.3 ?
C1 C2 H2A . . 119.3 ?
C4 C3 C2 . . 118.33(16) ?
C4 C3 H3A . . 120.8 ?
C2 C3 H3A . . 120.8 ?
F C4 C3 . . 118.60(16) ?
F C4 C5 . . 118.96(15) ?
C3 C4 C5 . . 122.45(16) ?
C4 C5 C6 . . 118.50(15) ?
C4 C5 H5A . . 120.8 ?
C6 C5 H5A . . 120.8 ?
C5 C6 C1 . . 121.24(15) ?
C5 C6 H6A . . 119.4 ?
C1 C6 H6A . . 119.4 ?
O1 C7 C8 . . 121.74(15) ?
O1 C7 C1 . . 120.62(13) ?
C8 C7 C1 . . 117.64(12) ?
C9 C8 C7 . . 121.69(14) ?
C9 C8 H8A . . 119.2 ?
C7 C8 H8A . . 119.2 ?
C8 C9 C10 . . 127.76(14) ?
C8 C9 H9A . . 116.1 ?
C10 C9 H9A . . 116.1 ?
C11 C10 C15 . . 120.04(13) ?
C11 C10 C9 . . 118.17(13) ?
C15 C10 C9 . . 121.77(13) ?
C12 C11 C10 . . 120.19(13) ?
C12 C11 H11A . . 119.9 ?
C10 C11 H11A . . 119.9 ?
O2 C12 C11 . . 124.36(13) ?
O2 C12 C13 . . 115.61(13) ?
C11 C12 C13 . . 119.98(13) ?
O3 C13 C12 . . 119.54(13) ?
O3 C13 C14 . . 120.55(13) ?
C12 C13 C14 . . 119.88(14) ?
O4 C14 C15 . . 124.71(14) ?
O4 C14 C13 . . 114.82(13) ?
C15 C14 C13 . . 120.47(13) ?
C14 C15 C10 . . 119.45(14) ?
C14 C15 H15A . . 120.3 ?
C10 C15 H15A . . 120.3 ?
O2 C16 H16A . . 109.5 ?
O2 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
O2 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
O3 C17 H17A . . 109.5 ?
O3 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
O3 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
O4 C18 H18A . . 109.5 ?
O4 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
O4 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
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
O4 C14 . 1.3602(18) ?
O4 C18 . 1.423(2) ?
F C4 . 1.350(2) ?
O1 C7 . 1.2218(18) ?
O2 C12 . 1.3635(18) ?
O2 C16 . 1.420(2) ?
O3 C13 . 1.3734(19) ?
O3 C17 . 1.417(2) ?
C1 C2 . 1.384(2) ?
C1 C6 . 1.391(2) ?
C1 C7 . 1.490(2) ?
C2 C3 . 1.378(2) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.367(2) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.368(3) ?
C5 C6 . 1.374(3) ?
C5 H5A . 0.9300 ?
C6 H6A . 0.9300 ?
C7 C8 . 1.477(2) ?
C8 C9 . 1.322(2) ?
C8 H8A . 0.9300 ?
C9 C10 . 1.463(2) ?
C9 H9A . 0.9300 ?
C10 C11 . 1.393(2) ?
C10 C15 . 1.400(2) ?
C11 C12 . 1.385(2) ?
C11 H11A . 0.9300 ?
C12 C13 . 1.390(2) ?
C13 C14 . 1.396(2) ?
C14 C15 . 1.384(2) ?
C15 H15A . 0.9300 ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 0.9600 ?
C17 H17A . 0.9600 ?
C17 H17B . 0.9600 ?
C17 H17C . 0.9600 ?
C18 H18A . 0.9600 ?
C18 H18B . 0.9600 ?
C18 H18C . 0.9600 ?
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
C3 H3A Cg2 4_575 0.93 2.91 3.6571(19) 138.0
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 . . . . -0.2(2) ?
C7 C1 C2 C3 . . . . -179.40(14) ?
C1 C2 C3 C4 . . . . -0.9(3) ?
C2 C3 C4 F . . . . -178.84(16) ?
C2 C3 C4 C5 . . . . 1.0(3) ?
F C4 C5 C6 . . . . 179.78(15) ?
C3 C4 C5 C6 . . . . -0.1(3) ?
C4 C5 C6 C1 . . . . -1.0(3) ?
C2 C1 C6 C5 . . . . 1.2(2) ?
C7 C1 C6 C5 . . . . -179.61(15) ?
C2 C1 C7 O1 . . . . 149.90(16) ?
C6 C1 C7 O1 . . . . -29.3(2) ?
C2 C1 C7 C8 . . . . -30.8(2) ?
C6 C1 C7 C8 . . . . 150.00(14) ?
O1 C7 C8 C9 . . . . 4.9(2) ?
C1 C7 C8 C9 . . . . -174.35(14) ?
C7 C8 C9 C10 . . . . 177.60(14) ?
C8 C9 C10 C11 . . . . -177.15(15) ?
C8 C9 C10 C15 . . . . 4.0(2) ?
C15 C10 C11 C12 . . . . -0.3(2) ?
C9 C10 C11 C12 . . . . -179.18(14) ?
C16 O2 C12 C11 . . . . 14.4(2) ?
C16 O2 C12 C13 . . . . -168.15(15) ?
C10 C11 C12 O2 . . . . 177.51(14) ?
C10 C11 C12 C13 . . . . 0.2(2) ?
C17 O3 C13 C12 . . . . 104.04(17) ?
C17 O3 C13 C14 . . . . -78.13(19) ?
O2 C12 C13 O3 . . . . 0.4(2) ?
C11 C12 C13 O3 . . . . 177.92(13) ?
O2 C12 C13 C14 . . . . -177.47(13) ?
C11 C12 C13 C14 . . . . 0.1(2) ?
C18 O4 C14 C15 . . . . -2.9(3) ?
C18 O4 C14 C13 . . . . 177.40(16) ?
O3 C13 C14 O4 . . . . 1.6(2) ?
C12 C13 C14 O4 . . . . 179.41(14) ?
O3 C13 C14 C15 . . . . -178.09(15) ?
C12 C13 C14 C15 . . . . -0.3(2) ?
O4 C14 C15 C10 . . . . -179.47(15) ?
C13 C14 C15 C10 . . . . 0.2(2) ?
C11 C10 C15 C14 . . . . 0.1(2) ?
C9 C10 C15 C14 . . . . 178.96(14) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4503169
