#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/62/2016293.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_2016293
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 Cl F O2'
_chemical_formula_moiety         'C21 H14 Cl F O2'
_chemical_formula_sum            'C21 H14 Cl F O2'
_chemical_formula_weight         352.77
_chemical_name_systematic
;
(2E)-1-(4-chlorophenyl)-3-(2-fluoro-4-phenoxyphenyl)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                99.109(7)
_cell_angle_beta                 104.800(8)
_cell_angle_gamma                113.697(9)
_cell_formula_units_Z            2
_cell_length_a                   9.045(6)
_cell_length_b                   9.833(6)
_cell_length_c                   11.474(7)
_cell_measurement_reflns_used    965
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      25.6
_cell_measurement_theta_min      1.8
_cell_volume                     863.3(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 0.961
_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  0.0246
_diffrn_reflns_av_sigmaI/netI    0.0306
_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       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8889
_diffrn_reflns_reduction_process
;
?
;
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.36
_diffrn_reflns_theta_min         1.92
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.242
_exptl_absorpt_correction_T_max  0.9692
_exptl_absorpt_correction_T_min  0.9207
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.172
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         3395
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0662
_refine_ls_R_factor_gt           0.0453
_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)+(0.0598P)²+0.1181P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1105
_refine_ls_wR_factor_ref         0.1341
_reflns_number_gt                2672
_reflns_number_total             3395
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            av3115.cif
_cod_data_source_block           III
_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_database_code               2016293
_cod_database_fobs_code          2016293
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
Cl Cl1 0.80478(8) -0.08233(8) 1.54625(6) 0.0844(2) Uani d 1
F F1 0.3850(2) 0.53648(17) 0.67286(14) 0.0977(5) Uani d 1
O O1 0.17510(18) -0.0423(2) 1.12692(15) 0.0821(5) Uani d 1
O O2 0.0572(2) 0.35710(18) 0.66076(13) 0.0764(5) Uani d 1
C C1 0.6701(3) -0.0510(2) 1.42744(18) 0.0587(5) Uani d 1
C C2 0.4951(3) -0.1411(3) 1.3894(2) 0.0641(5) Uani d 1
C C3 0.3879(3) -0.1147(3) 1.2967(2) 0.0625(5) Uani d 1
C C4 0.4542(2) 0.0022(2) 1.24170(17) 0.0531(4) Uani d 1
C C5 0.6326(3) 0.0909(3) 1.2821(2) 0.0618(5) Uani d 1
C C6 0.7412(3) 0.0657(3) 1.3758(2) 0.0665(5) Uani d 1
C C7 0.3295(2) 0.0254(2) 1.14370(18) 0.0584(5) Uani d 1
C C8 0.3895(3) 0.1278(2) 1.06718(19) 0.0592(5) Uani d 1
C C9 0.2777(3) 0.1439(3) 0.97700(19) 0.0595(5) Uani d 1
C C10 0.3106(2) 0.2425(2) 0.89503(17) 0.0552(5) Uani d 1
C C11 0.1716(3) 0.2531(3) 0.81658(19) 0.0618(5) Uani d 1
C C12 0.1963(3) 0.3517(2) 0.74220(18) 0.0627(5) Uani d 1
C C13 0.3606(3) 0.4386(3) 0.7448(2) 0.0682(6) Uani d 1
C C14 0.4998(3) 0.4288(3) 0.8190(2) 0.0705(6) Uani d 1
C C15 0.4744(3) 0.3311(2) 0.89346(19) 0.0606(5) Uani d 1
C C16 0.0107(3) 0.4685(2) 0.7048(2) 0.0607(5) Uani d 1
C C17 0.0689(3) 0.5504(3) 0.8294(2) 0.0765(6) Uani d 1
C C18 0.0146(4) 0.6599(4) 0.8621(3) 0.0957(9) Uani d 1
C C19 -0.0963(4) 0.6846(4) 0.7712(4) 0.0970(10) Uani d 1
C C20 -0.1569(4) 0.5991(3) 0.6481(3) 0.0878(8) Uani d 1
C C21 -0.1036(3) 0.4910(3) 0.6142(2) 0.0705(6) Uani d 1
H H2 0.447(3) -0.223(3) 1.428(2) 0.076(6) Uiso d 1
H H3 0.265(3) -0.180(3) 1.266(2) 0.091(8) Uiso d 1
H H5 0.686(3) 0.173(3) 1.249(2) 0.075(6) Uiso d 1
H H6 0.863(3) 0.128(3) 1.406(2) 0.092(8) Uiso d 1
H H8 0.509(3) 0.181(3) 1.079(2) 0.076(6) Uiso d 1
H H9 0.163(3) 0.088(2) 0.967(2) 0.072(6) Uiso d 1
H H11 0.059(3) 0.193(2) 0.8184(17) 0.056(5) Uiso d 1
H H14 0.604(3) 0.488(3) 0.819(2) 0.088(8) Uiso d 1
H H15 0.572(3) 0.323(2) 0.948(2) 0.065(6) Uiso d 1
H H17 0.135(3) 0.531(3) 0.888(2) 0.077(7) Uiso d 1
H H18 0.052(3) 0.708(3) 0.942(2) 0.092(7) Uiso d 1
H H19 -0.125(4) 0.756(4) 0.797(3) 0.128(12) Uiso d 1
H H20 -0.236(3) 0.623(3) 0.584(3) 0.103(8) Uiso d 1
H H21 -0.147(3) 0.429(3) 0.522(2) 0.085(7) 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'
Cl Cl 0.1484 0.1585 '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
C5 C4 C3 118.09(18) ?
C5 C4 C7 123.88(18) yes
C3 C4 C7 118.03(18) ?
C9 C8 C7 120.7(2) ?
C9 C8 H8 118.7(15) ?
C7 C8 H8 120.5(14) ?
C15 C10 C11 118.2(2) ?
C15 C10 C9 123.31(18) ?
C11 C10 C9 118.50(19) ?
C12 O2 C16 117.69(15) ?
O1 C7 C8 119.80(18) ?
O1 C7 C4 119.35(18) ?
C8 C7 C4 120.85(17) ?
C2 C1 C6 121.57(19) ?
C2 C1 Cl1 118.99(17) ?
C6 C1 Cl1 119.42(17) ?
C1 C6 C5 119.0(2) ?
C1 C6 H6 119.8(16) ?
C5 C6 H6 121.2(17) ?
C2 C3 C4 121.3(2) ?
C2 C3 H3 120.2(16) ?
C4 C3 H3 118.5(16) ?
C8 C9 C10 129.2(2) yes
C8 C9 H9 115.9(15) ?
C10 C9 H9 114.9(14) ?
C13 C12 C11 118.77(19) ?
C13 C12 O2 120.2(2) ?
C11 C12 O2 120.9(2) ?
C12 C11 C10 121.1(2) ?
C12 C11 H11 120.8(12) ?
C10 C11 H11 118.0(12) ?
C1 C2 C3 119.1(2) ?
C1 C2 H2 120.1(13) ?
C3 C2 H2 120.8(14) ?
C6 C5 C4 120.9(2) ?
C6 C5 H5 116.7(14) ?
C4 C5 H5 122.3(14) ?
C17 C16 C21 120.6(2) ?
C17 C16 O2 123.8(2) ?
C21 C16 O2 115.53(19) ?
C14 C15 C10 121.0(2) ?
C14 C15 H15 120.7(13) ?
C10 C15 H15 118.3(13) ?
C15 C14 C13 119.3(2) ?
C15 C14 H14 121.8(17) ?
C13 C14 H14 118.8(17) ?
C20 C21 C16 120.0(3) ?
C20 C21 H21 119.9(14) ?
C16 C21 H21 120.1(14) ?
C16 C17 C18 118.6(3) ?
C16 C17 H17 120.8(15) ?
C18 C17 H17 120.6(15) ?
F1 C13 C12 118.8(2) ?
F1 C13 C14 119.7(2) ?
C12 C13 C14 121.6(2) ?
C19 C20 C21 120.0(3) ?
C19 C20 H20 117.3(15) ?
C21 C20 H20 122.6(15) ?
C19 C18 C17 120.6(3) ?
C19 C18 H18 123.4(16) ?
C17 C18 H18 115.9(16) ?
C20 C19 C18 120.1(3) ?
C20 C19 H19 123(2) ?
C18 C19 H19 117(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C1 1.739(2) ?
C4 C5 1.392(3) ?
C4 C3 1.395(3) ?
C4 C7 1.493(3) yes
C8 C9 1.328(3) yes
C8 C7 1.471(3) yes
C8 H8 0.95(2) ?
C10 C15 1.391(3) ?
C10 C11 1.399(3) ?
C10 C9 1.454(3) yes
O2 C12 1.389(2) yes
O2 C16 1.391(2) yes
O1 C7 1.227(2) yes
C1 C2 1.371(3) ?
C1 C6 1.377(3) ?
C6 C5 1.387(3) ?
C6 H6 0.95(3) ?
C3 C2 1.379(3) ?
C3 H3 0.96(3) ?
C9 H9 0.92(2) ?
C12 C13 1.374(3) ?
C12 C11 1.380(3) ?
C11 H11 0.96(2) ?
C2 H2 0.98(3) ?
C5 H5 0.96(2) ?
C16 C17 1.371(3) ?
C16 C21 1.381(3) ?
C15 C14 1.374(3) ?
C15 H15 0.99(2) ?
C14 C13 1.377(3) ?
C14 H14 0.89(3) ?
C21 C20 1.376(3) ?
C21 H21 1.02(2) ?
C17 C18 1.390(4) ?
C17 H17 0.88(2) ?
C13 F1 1.352(3) ?
C20 C19 1.363(5) ?
C20 H20 1.01(3) ?
C18 C19 1.376(5) ?
C18 H18 0.87(2) ?
C19 H19 0.88(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 0.96(2) 2.35(2) 3.285(3) 165(2) yes
C18 H18 O1 1_565 0.87(2) 2.59(2) 3.381(4) 151(2) yes
C5 H5 Cg3 2_665 0.96(2) 3.13(3) 3.940(4) 144(2) 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
C9 C8 C7 O1 -2.3(3) ?
C9 C8 C7 C4 177.57(17) yes
C5 C4 C7 O1 -169.50(19) ?
C3 C4 C7 O1 10.0(3) ?
C5 C4 C7 C8 10.7(3) ?
C3 C4 C7 C8 -169.80(18) yes
C2 C1 C6 C5 -0.8(3) ?
Cl1 C1 C6 C5 -179.30(15) ?
C5 C4 C3 C2 0.7(3) ?
C7 C4 C3 C2 -178.81(18) ?
C7 C8 C9 C10 177.47(18) yes
C15 C10 C9 C8 5.3(3) ?
C11 C10 C9 C8 -172.6(2) yes
C16 O2 C12 C13 -89.9(2) ?
C16 O2 C12 C11 93.7(2) yes
C13 C12 C11 C10 1.0(3) ?
O2 C12 C11 C10 177.40(16) ?
C15 C10 C11 C12 -1.8(3) ?
C9 C10 C11 C12 176.17(18) ?
C6 C1 C2 C3 0.5(3) ?
Cl1 C1 C2 C3 178.94(15) ?
C4 C3 C2 C1 -0.4(3) ?
C1 C6 C5 C4 1.2(3) ?
C3 C4 C5 C6 -1.1(3) ?
C7 C4 C5 C6 178.41(18) ?
C12 O2 C16 C17 -14.0(3) yes
C12 O2 C16 C21 167.34(19) ?
C11 C10 C15 C14 1.4(3) ?
C9 C10 C15 C14 -176.51(19) ?
C10 C15 C14 C13 -0.1(3) ?
C17 C16 C21 C20 1.6(3) ?
O2 C16 C21 C20 -179.7(2) ?
C21 C16 C17 C18 -1.9(4) ?
O2 C16 C17 C18 179.4(2) ?
C11 C12 C13 F1 -179.31(18) ?
O2 C12 C13 F1 4.3(3) ?
C11 C12 C13 C14 0.3(3) ?
O2 C12 C13 C14 -176.14(18) ?
C15 C14 C13 F1 178.88(19) ?
C15 C14 C13 C12 -0.7(3) ?
C16 C21 C20 C19 0.3(4) ?
C16 C17 C18 C19 0.5(4) ?
C21 C20 C19 C18 -1.7(4) ?
C17 C18 C19 C20 1.3(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654086
