#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/62/2016292.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_2016292
loop_
_publ_author_name
'Chopra, Deepak'
'Mohan, T. P.'
'Vishalakshi, B.'
'Guru Row, T. N.'
_publ_section_title
;
 A series of substituted
 (2E)-3-(2-fluoro-4-phenoxyphenyl)-1-phenylprop-2-en-1-ones
;
_journal_coeditor_code           AV3115
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o704
_journal_page_last               o710
_journal_paper_doi               10.1107/S0108270107049426
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C21 H14 F2 O2'
_chemical_formula_moiety         'C21 H14 F2 O2'
_chemical_formula_sum            'C21 H14 F2 O2'
_chemical_formula_weight         336.32
_chemical_name_systematic
;
(2E)-3-(2-fluoro-4-phenoxyphenyl)-1-(4-fluorophenyl)prop-2-en-1-one
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                97.362(10)
_cell_angle_beta                 101.898(9)
_cell_angle_gamma                108.731(9)
_cell_formula_units_Z            2
_cell_length_a                   8.164(5)
_cell_length_b                   10.036(6)
_cell_length_c                   11.136(7)
_cell_measurement_reflns_used    775
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      25.2
_cell_measurement_theta_min      1.4
_cell_volume                     826.7(9)
_computing_cell_refinement       'SMART (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics
'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)'
_computing_publication_material  'PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al.,  1993)'
_diffrn_ambient_temperature      290(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0165
_diffrn_reflns_av_sigmaI/netI    0.0216
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8638
_diffrn_reflns_reduction_process
;
?
;
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.35
_diffrn_reflns_theta_min         1.91
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.9940
_exptl_absorpt_correction_T_min  0.9443
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       'plate '
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.122
_refine_diff_density_min         -0.192
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         3291
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0696
_refine_ls_R_factor_gt           0.0424
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0622P)²+0.0408P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1047
_refine_ls_wR_factor_ref         0.1176
_reflns_number_gt                2205
_reflns_number_total             3291
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            av3115.cif
_cod_data_source_block           II
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        826.8(9)
_cod_database_code               2016292
_cod_database_fobs_code          2016292
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
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_occupancy
F F1 0.37217(15) 0.54948(11) 0.68943(10) 0.0887(4) Uani d 1
F F2 0.83443(16) -0.04147(15) 1.56720(12) 0.1073(4) Uani d 1
O O1 0.21063(19) -0.08620(17) 1.11312(13) 0.1068(5) Uani d 1
O O2 0.03588(16) 0.36217(12) 0.67485(11) 0.0756(4) Uani d 1
C C1 0.7219(3) -0.0300(2) 1.46365(17) 0.0717(5) Uani d 1
C C2 0.5551(3) -0.1331(2) 1.41942(18) 0.0711(5) Uani d 1
C C3 0.4404(3) -0.11863(18) 1.31695(16) 0.0647(4) Uani d 1
C C4 0.4925(2) -0.00337(15) 1.25774(13) 0.0537(4) Uani d 1
C C5 0.6633(2) 0.09816(18) 1.30612(16) 0.0629(4) Uani d 1
C C6 0.7799(3) 0.0859(2) 1.41007(18) 0.0737(5) Uani d 1
C C7 0.3617(2) 0.00398(18) 1.14640(15) 0.0631(4) Uani d 1
C C8 0.4118(2) 0.11838(18) 1.07501(15) 0.0595(4) Uani d 1
C C9 0.2936(2) 0.13165(18) 0.98114(15) 0.0620(4) Uani d 1
C C10 0.3201(2) 0.23957(16) 0.90318(14) 0.0557(4) Uani d 1
C C11 0.1693(2) 0.25153(18) 0.82563(15) 0.0615(4) Uani d 1
C C12 0.1868(2) 0.35544(17) 0.75469(14) 0.0615(4) Uani d 1
C C13 0.3558(2) 0.44685(17) 0.75926(15) 0.0634(4) Uani d 1
C C14 0.5068(2) 0.43697(19) 0.83293(16) 0.0642(4) Uani d 1
C C15 0.4880(2) 0.33308(17) 0.90426(15) 0.0592(4) Uani d 1
C C16 -0.0158(2) 0.47810(16) 0.70489(15) 0.0606(4) Uani d 1
C C17 0.0394(2) 0.5635(2) 0.82288(19) 0.0729(5) Uani d 1
C C18 -0.0181(3) 0.6791(2) 0.8418(3) 0.0882(6) Uani d 1
C C19 -0.1305(3) 0.7051(3) 0.7448(3) 0.0926(7) Uani d 1
C C20 -0.1876(3) 0.6162(3) 0.6296(2) 0.0905(7) Uani d 1
C C21 -0.1322(2) 0.5024(2) 0.6085(2) 0.0732(5) Uani d 1
H H2 0.517(2) -0.2113(19) 1.4593(17) 0.079(5) Uiso d 1
H H3 0.323(3) -0.187(2) 1.2838(17) 0.081(6) Uiso d 1
H H5 0.706(2) 0.1796(18) 1.2666(15) 0.070(5) Uiso d 1
H H6 0.895(3) 0.154(2) 1.4414(18) 0.089(6) Uiso d 1
H H8 0.531(3) 0.1797(19) 1.0988(16) 0.078(5) Uiso d 1
H H9 0.175(3) 0.0639(19) 0.9656(17) 0.084(6) Uiso d 1
H H11 0.053(2) 0.1887(17) 0.8247(14) 0.063(4) Uiso d 1
H H14 0.621(3) 0.4998(19) 0.8320(16) 0.076(5) Uiso d 1
H H15 0.592(2) 0.3252(16) 0.9564(15) 0.063(4) Uiso d 1
H H17 0.112(2) 0.5395(18) 0.8877(17) 0.072(5) Uiso d 1
H H18 0.022(3) 0.731(2) 0.921(2) 0.093(7) Uiso d 1
H H19 -0.168(3) 0.786(2) 0.7597(19) 0.103(7) Uiso d 1
H H20 -0.273(3) 0.634(2) 0.558(2) 0.114(7) Uiso d 1
H H21 -0.168(3) 0.442(2) 0.529(2) 0.089(6) Uiso d 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'
C C 0.0033 0.0016 '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
_geom_angle_publ_flag
C15 C10 C11 118.16(15) ?
C15 C10 C9 123.09(14) ?
C11 C10 C9 118.73(15) ?
C16 O2 C12 118.17(12) ?
C12 C11 C10 120.96(16) ?
C12 C11 H11 120.0(9) ?
C10 C11 H11 119.0(9) ?
C13 C14 C15 119.00(16) ?
C13 C14 H14 119.4(10) ?
C15 C14 H14 121.6(10) ?
C8 C9 C10 128.49(16) yes
C8 C9 H9 114.7(11) ?
C10 C9 H9 116.8(11) ?
C13 C12 C11 119.03(15) ?
C13 C12 O2 120.85(15) ?
C11 C12 O2 120.04(15) ?
C5 C4 C3 118.07(15) ?
C5 C4 C7 123.47(14) yes
C3 C4 C7 118.46(15) ?
C9 C8 C7 121.68(16) ?
C9 C8 H8 121.8(11) ?
C7 C8 H8 116.6(11) ?
C2 C3 C4 121.56(18) ?
C2 C3 H3 121.0(11) ?
C4 C3 H3 117.5(11) ?
O1 C7 C8 119.37(16) ?
O1 C7 C4 119.45(15) ?
C8 C7 C4 121.17(14) ?
F1 C13 C14 119.65(15) ?
F1 C13 C12 118.74(15) ?
C14 C13 C12 121.60(15) ?
C1 C6 C5 118.27(18) ?
C1 C6 H6 121.0(12) ?
C5 C6 H6 120.7(12) ?
C14 C15 C10 121.24(16) ?
C14 C15 H15 119.9(10) ?
C10 C15 H15 118.9(9) ?
C4 C5 C6 121.08(16) ?
C4 C5 H5 120.8(10) ?
C6 C5 H5 118.1(10) ?
C17 C16 C21 120.76(18) ?
C17 C16 O2 123.35(15) ?
C21 C16 O2 115.87(16) ?
F2 C1 C2 118.42(17) ?
F2 C1 C6 118.64(18) ?
C2 C1 C6 122.92(17) ?
C1 C2 C3 118.09(17) ?
C1 C2 H2 121.6(11) ?
C3 C2 H2 120.3(11) ?
C20 C21 C16 119.6(2) ?
C20 C21 H21 121.3(12) ?
C16 C21 H21 119.0(12) ?
C16 C17 C18 118.5(2) ?
C16 C17 H17 118.3(10) ?
C18 C17 H17 123.3(11) ?
C19 C18 C17 120.6(2) ?
C19 C18 H18 124.8(14) ?
C17 C18 H18 114.6(14) ?
C20 C19 C18 119.8(2) ?
C20 C19 H19 120.8(13) ?
C18 C19 H19 119.4(13) ?
C19 C20 C21 120.7(2) ?
C19 C20 H20 119.9(13) ?
C21 C20 H20 119.4(13) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C10 C15 1.387(2) ?
C10 C11 1.400(2) ?
C10 C9 1.463(2) yes
F1 C13 1.3576(19) ?
O2 C16 1.385(2) yes
O2 C12 1.3895(19) yes
C11 C12 1.376(2) ?
C11 H11 0.953(17) ?
C14 C13 1.373(2) ?
C14 C15 1.379(2) ?
C14 H14 0.947(19) ?
C9 C8 1.321(2) yes
C9 H9 0.955(19) ?
C12 C13 1.376(2) ?
C4 C5 1.382(2) ?
C4 C3 1.396(2) ?
C4 C7 1.487(2) yes
C8 C7 1.478(2) yes
C8 H8 0.932(19) ?
F2 C1 1.361(2) ?
C3 C2 1.375(3) ?
C3 H3 0.944(19) ?
C7 O1 1.219(2) yes
C6 C1 1.369(3) ?
C6 C5 1.385(2) ?
C6 H6 0.93(2) ?
C15 H15 0.959(16) ?
C5 H5 0.978(17) ?
C16 C17 1.373(3) ?
C16 C21 1.382(2) ?
C1 C2 1.362(3) ?
C2 H2 0.949(18) ?
C21 C20 1.368(3) ?
C21 H21 0.94(2) ?
C17 C18 1.392(3) ?
C17 H17 0.946(18) ?
C18 C19 1.376(3) ?
C18 H18 0.90(2) ?
C19 C20 1.361(3) ?
C19 H19 0.97(2) ?
C20 H20 1.02(2) ?
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
C11 H11 O1 2_557 0.95(2) 2.36(2) 3.271(3) 161(2) yes
C18 H18 O1 1_565 0.90(2) 2.48(2) 3.345(3) 162(2) yes
C5 H5 Cg3 2_665 0.98(2) 3.12(2) 3.894(3) 137.0(10) yes
C14 H14 Cg3 1_455 0.95(2) 2.91(2) 3.780(3) 153.0(10) yes
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
_geom_torsion_publ_flag
C15 C10 C11 C12 -1.6(2) ?
C9 C10 C11 C12 177.14(15) ?
C15 C10 C9 C8 11.4(3) ?
C11 C10 C9 C8 -167.27(17) yes
C10 C11 C12 C13 1.0(2) ?
C10 C11 C12 O2 177.66(13) ?
C16 O2 C12 C13 -72.5(2) ?
C16 O2 C12 C11 110.98(18) yes
C10 C9 C8 C7 178.70(15) yes
C5 C4 C3 C2 -0.9(2) ?
C7 C4 C3 C2 179.22(15) ?
C9 C8 C7 O1 4.8(3) ?
C9 C8 C7 C4 -175.44(15) yes
C5 C4 C7 O1 -176.52(17) ?
C3 C4 C7 O1 3.4(2) ?
C5 C4 C7 C8 3.7(2) ?
C3 C4 C7 C8 -176.41(14) yes
C15 C14 C13 F1 179.39(14) ?
C15 C14 C13 C12 -0.2(3) ?
C11 C12 C13 F1 -179.75(14) ?
O2 C12 C13 F1 3.7(2) ?
C11 C12 C13 C14 -0.1(3) ?
O2 C12 C13 C14 -176.72(15) ?
C13 C14 C15 C10 -0.3(2) ?
C11 C10 C15 C14 1.2(2) ?
C9 C10 C15 C14 -177.44(15) ?
C3 C4 C5 C6 0.2(2) ?
C7 C4 C5 C6 -179.90(15) ?
C1 C6 C5 C4 0.3(3) ?
C12 O2 C16 C17 -18.9(2) yes
C12 O2 C16 C21 162.58(15) ?
C5 C6 C1 F2 -178.81(15) ?
C5 C6 C1 C2 -0.2(3) ?
F2 C1 C2 C3 178.17(15) ?
C6 C1 C2 C3 -0.5(3) ?
C4 C3 C2 C1 1.0(3) ?
C17 C16 C21 C20 2.5(3) ?
O2 C16 C21 C20 -178.93(16) ?
C21 C16 C17 C18 -2.8(3) ?
O2 C16 C17 C18 178.72(16) ?
C16 C17 C18 C19 1.2(3) ?
C17 C18 C19 C20 0.7(3) ?
C18 C19 C20 C21 -1.1(3) ?
C16 C21 C20 C19 -0.5(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654085
