#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/62/2016294.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_2016294
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          'C22 H17 F O2'
_chemical_formula_moiety         'C22 H17 F O2'
_chemical_formula_sum            'C22 H17 F O2'
_chemical_formula_weight         332.36
_chemical_name_systematic
;
(2E)-3-(2-fluoro-4-phenoxyphenyl)-1-(4-methylphenyl)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                98.887(9)
_cell_angle_beta                 104.304(9)
_cell_angle_gamma                113.754(8)
_cell_formula_units_Z            2
_cell_length_a                   9.196(5)
_cell_length_b                   9.726(5)
_cell_length_c                   11.554(7)
_cell_measurement_reflns_used    795
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      26.4
_cell_measurement_theta_min      1.7
_cell_volume                     878.1(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 0.995
_diffrn_measured_fraction_theta_max 0.969
_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  0.0140
_diffrn_reflns_av_sigmaI/netI    0.0161
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9092
_diffrn_reflns_reduction_process
;
?
;
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         1.90
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9897
_exptl_absorpt_correction_T_min  0.9402
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.128
_refine_diff_density_min         -0.164
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         3476
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0447
_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)+(0.0597P)²+0.0991P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1120
_refine_ls_wR_factor_ref         0.1242
_reflns_number_gt                2575
_reflns_number_total             3476
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            av3115.cif
_cod_data_source_block           IV
_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        878.2(9)
_cod_database_code               2016294
_cod_database_fobs_code          2016294
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
O O1 0.17659(14) -0.04092(16) 1.13449(11) 0.0907(4) Uani d 1
O O2 0.06739(15) 0.36096(14) 0.66600(10) 0.0844(4) Uani d 1
F F1 0.38959(15) 0.53565(13) 0.67279(10) 0.1047(4) Uani d 1
C C1 0.6681(2) -0.05428(18) 1.42690(14) 0.0668(4) Uani d 1
C C2 0.4938(2) -0.1431(2) 1.38939(16) 0.0728(4) Uani d 1
C C3 0.3865(2) -0.11751(19) 1.29901(15) 0.0685(4) Uani d 1
C C4 0.45019(17) -0.00169(16) 1.24141(13) 0.0590(4) Uani d 1
C C5 0.6250(2) 0.08632(19) 1.27797(16) 0.0695(4) Uani d 1
C C6 0.7315(2) 0.0602(2) 1.36934(16) 0.0740(4) Uani d 1
C C7 0.32788(19) 0.02334(18) 1.14699(14) 0.0640(4) Uani d 1
C C8 0.3861(2) 0.12508(18) 1.06832(14) 0.0649(4) Uani d 1
C C9 0.2770(2) 0.14442(19) 0.98197(14) 0.0648(4) Uani d 1
C C10 0.31118(18) 0.24397(16) 0.89912(13) 0.0602(4) Uani d 1
C C11 0.1763(2) 0.25677(19) 0.82261(14) 0.0661(4) Uani d 1
C C12 0.2026(2) 0.35441(19) 0.74715(14) 0.0676(4) Uani d 1
C C13 0.3648(2) 0.43956(19) 0.74719(15) 0.0730(4) Uani d 1
C C14 0.4997(2) 0.4273(2) 0.81945(16) 0.0739(4) Uani d 1
C C15 0.4725(2) 0.32965(18) 0.89480(14) 0.0655(4) Uani d 1
C C16 0.01872(19) 0.47103(18) 0.70882(15) 0.0667(4) Uani d 1
C C17 0.0755(2) 0.5551(2) 0.83148(18) 0.0822(5) Uani d 1
C C18 0.0179(3) 0.6631(3) 0.8624(3) 0.1039(7) Uani d 1
C C19 -0.0937(3) 0.6838(3) 0.7718(3) 0.1062(7) Uani d 1
C C20 -0.1520(3) 0.5954(3) 0.6516(3) 0.0987(6) Uani d 1
C C21 -0.0965(2) 0.4896(2) 0.61837(19) 0.0798(5) Uani d 1
C C22 0.7837(3) -0.0820(3) 1.5274(2) 0.0892(6) Uani d 1
H H2 0.446(2) -0.224(2) 1.4274(15) 0.080(5) Uiso d 1
H H3 0.267(2) -0.176(2) 1.2749(16) 0.088(5) Uiso d 1
H H5 0.673(2) 0.164(2) 1.2396(15) 0.077(5) Uiso d 1
H H6 0.850(2) 0.121(2) 1.3957(16) 0.085(5) Uiso d 1
H H8 0.505(2) 0.177(2) 1.0836(15) 0.081(5) Uiso d 1
H H9 0.160(2) 0.0865(19) 0.9748(15) 0.077(5) Uiso d 1
H H11 0.066(2) 0.1988(19) 0.8246(15) 0.075(5) Uiso d 1
H H14 0.606(2) 0.486(2) 0.8163(15) 0.085(5) Uiso d 1
H H15 0.570(2) 0.3187(17) 0.9463(14) 0.072(4) Uiso d 1
H H17 0.152(2) 0.536(2) 0.8917(17) 0.087(5) Uiso d 1
H H18 0.057(3) 0.708(3) 0.945(2) 0.106(7) Uiso d 1
H H19 -0.128(3) 0.761(3) 0.798(2) 0.131(8) Uiso d 1
H H20 -0.243(3) 0.606(3) 0.583(2) 0.132(8) Uiso d 1
H H21 -0.132(3) 0.427(2) 0.529(2) 0.111(7) Uiso d 1
H H22B 0.825(3) -0.147(3) 1.492(2) 0.126(8) Uiso d 1
H H22C 0.732(4) -0.121(4) 1.584(3) 0.163(11) Uiso d 1
H H22A 0.892(4) 0.017(4) 1.578(3) 0.168(11) 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 118.34(15) ?
C15 C10 C9 123.30(13) ?
C11 C10 C9 118.34(14) ?
C5 C4 C3 117.94(14) ?
C5 C4 C7 123.77(14) yes
C3 C4 C7 118.27(14) ?
C16 O2 C12 118.04(12) ?
C12 C11 C10 120.77(16) ?
C12 C11 H11 120.1(10) ?
C10 C11 H11 119.1(10) ?
C9 C8 C7 120.75(15) ?
C9 C8 H8 122.1(10) ?
C7 C8 H8 117.1(10) ?
C8 C9 C10 128.49(15) yes
C8 C9 H9 114.8(10) ?
C10 C9 H9 116.7(10) ?
O1 C7 C8 119.68(14) ?
O1 C7 C4 119.71(14) ?
C8 C7 C4 120.61(13) ?
C2 C3 C4 120.79(16) ?
C2 C3 H3 121.3(11) ?
C4 C3 H3 117.9(11) ?
C11 C12 C13 119.15(15) ?
C11 C12 O2 120.83(15) ?
C13 C12 O2 119.90(15) ?
C13 C14 C15 118.97(17) ?
C13 C14 H14 118.9(11) ?
C15 C14 H14 122.2(11) ?
C6 C1 C2 117.94(15) ?
C6 C1 C22 121.38(18) ?
C2 C1 C22 120.69(17) ?
C6 C5 C4 120.79(16) ?
C6 C5 H5 118.8(10) ?
C4 C5 H5 120.4(10) ?
C17 C16 C21 121.04(17) ?
C17 C16 O2 123.88(15) ?
C21 C16 O2 115.07(15) ?
C5 C6 C1 121.19(16) ?
C5 C6 H6 121.2(11) ?
C1 C6 H6 117.6(11) ?
C3 C2 C1 121.35(16) ?
C3 C2 H2 118.7(10) ?
C1 C2 H2 120.0(10) ?
C14 C15 C10 121.20(15) ?
C14 C15 H15 119.2(9) ?
C10 C15 H15 119.6(9) ?
F1 C13 C14 119.67(16) ?
F1 C13 C12 118.79(16) ?
C14 C13 C12 121.54(16) ?
C20 C21 C16 119.4(2) ?
C20 C21 H21 122.7(12) ?
C16 C21 H21 117.9(12) ?
C1 C22 H22B 110.5(14) ?
C1 C22 H22C 111.6(18) ?
H22B C22 H22C 113(2) ?
C1 C22 H22A 112.6(17) ?
H22B C22 H22A 102(2) ?
H22C C22 H22A 107(2) ?
C16 C17 C18 118.3(2) ?
C16 C17 H17 118.6(11) ?
C18 C17 H17 123.0(11) ?
C19 C18 C17 120.5(2) ?
C19 C18 H18 127.2(14) ?
C17 C18 H18 112.2(14) ?
C19 C20 C21 120.8(2) ?
C19 C20 H20 120.4(13) ?
C21 C20 H20 118.8(13) ?
C20 C19 C18 120.0(2) ?
C20 C19 H19 122.8(15) ?
C18 C19 H19 117.2(15) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C10 C15 1.397(2) ?
C10 C11 1.397(2) ?
C10 C9 1.464(2) yes
C4 C5 1.392(2) ?
C4 C3 1.395(2) ?
C4 C7 1.487(2) yes
O2 C16 1.387(2) yes
O2 C12 1.3911(19) yes
C11 C12 1.377(2) ?
C11 H11 0.951(18) ?
C8 C9 1.324(2) yes
C8 C7 1.478(2) yes
C8 H8 0.954(18) ?
C9 H9 0.964(18) ?
C7 O1 1.2326(19) yes
C3 C2 1.376(2) ?
C3 H3 0.949(19) ?
C12 C13 1.384(3) ?
C14 C13 1.374(3) ?
C14 C15 1.376(2) ?
C14 H14 0.925(18) ?
C1 C6 1.385(2) ?
C1 C2 1.389(2) ?
C1 C22 1.507(2) ?
C5 C6 1.383(2) ?
C5 H5 0.945(17) ?
F1 C13 1.356(2) ?
C16 C17 1.372(2) ?
C16 C21 1.383(2) ?
C6 H6 0.946(19) ?
C2 H2 0.962(18) ?
C15 H15 1.001(16) ?
C21 C20 1.366(3) ?
C21 H21 1.01(2) ?
C22 H22B 0.95(3) ?
C22 H22C 0.94(3) ?
C22 H22A 1.01(3) ?
C17 C18 1.392(3) ?
C17 H17 0.954(18) ?
C18 C19 1.375(4) ?
C18 H18 0.89(2) ?
C20 C19 1.359(4) ?
C20 H20 1.05(2) ?
C19 H19 0.96(3) ?
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) 2.35(2) 3.288(3) 167(2) yes
C18 H18 O1 1_565 0.89(2) 2.64(2) 3.443(3) 150(2) yes
C5 H5 Cg3 2_665 0.95(2) 3.21(2) 3.980(3) 140.0(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 176.97(13) ?
C7 C8 C9 C10 177.56(13) yes
C15 C10 C9 C8 4.3(2) ?
C11 C10 C9 C8 -174.20(15) yes
C9 C8 C7 O1 -2.0(2) ?
C9 C8 C7 C4 178.26(13) yes
C5 C4 C7 O1 -168.08(15) ?
C3 C4 C7 O1 10.4(2) ?
C5 C4 C7 C8 11.7(2) ?
C3 C4 C7 C8 -169.90(13) yes
C5 C4 C3 C2 0.2(2) ?
C7 C4 C3 C2 -178.31(14) ?
C10 C11 C12 C13 0.4(2) ?
C10 C11 C12 O2 176.52(12) ?
C16 O2 C12 C11 91.19(18) yes
C16 O2 C12 C13 -92.74(18) ?
C3 C4 C5 C6 -0.5(2) ?
C7 C4 C5 C6 177.89(14) ?
C12 O2 C16 C17 -11.6(2) yes
C12 O2 C16 C21 169.66(14) ?
C4 C5 C6 C1 0.2(3) ?
C2 C1 C6 C5 0.5(2) ?
C22 C1 C6 C5 -179.35(17) ?
C4 C3 C2 C1 0.5(2) ?
C6 C1 C2 C3 -0.8(2) ?
C22 C1 C2 C3 179.02(17) ?
C13 C14 C15 C10 -0.2(2) ?
C11 C10 C15 C14 1.5(2) ?
C9 C10 C15 C14 -176.99(14) ?
C15 C14 C13 F1 179.79(14) ?
C15 C14 C13 C12 -1.0(2) ?
C11 C12 C13 F1 -179.89(13) ?
O2 C12 C13 F1 4.0(2) ?
C11 C12 C13 C14 0.9(2) ?
O2 C12 C13 C14 -175.24(14) ?
C17 C16 C21 C20 1.2(3) ?
O2 C16 C21 C20 180.00(16) ?
C21 C16 C17 C18 -1.8(3) ?
O2 C16 C17 C18 179.55(16) ?
C16 C17 C18 C19 0.3(3) ?
C16 C21 C20 C19 0.9(3) ?
C21 C20 C19 C18 -2.4(3) ?
C17 C18 C19 C20 1.8(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654087
