#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/93/2019385.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2019385
loop_
_publ_author_name
'Schwarzer, Anke'
'Weber, Edwin'
_publ_section_title
;
 Photochemical dimerization of a fluorinated dibenzylideneacetone in
 chloroform solution
;
_journal_coeditor_code           EG3145
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              202
_journal_page_last               206
_journal_paper_doi               10.1107/S2053229613034232
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C17 H10 F4 O'
_chemical_formula_moiety         'C17 H10 F4 O'
_chemical_formula_sum            'C17 H10 F4 O'
_chemical_formula_weight         306.25
_chemical_name_systematic
;
1,5-Bis(2,6-difluorophenyl)penta-1,4-dien-3-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 104.831(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.4793(6)
_cell_length_b                   15.6410(13)
_cell_length_c                   12.0962(11)
_cell_measurement_reflns_used    1695
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      26.91
_cell_measurement_theta_min      2.17
_cell_volume                     1367.9(2)
_computing_cell_refinement       'SMART (Bruker, 2007)'
_computing_data_collection       'SMART (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Bruker, 2007)'
_diffrn_ambient_temperature      93(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'phi and omega 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  0.0555
_diffrn_reflns_av_sigmaI/netI    0.0584
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10280
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         2.91
_exptl_absorpt_coefficient_mu    0.129
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.250
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2964
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.990
_refine_ls_R_factor_all          0.0888
_refine_ls_R_factor_gt           0.0438
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0590P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1015
_refine_ls_wR_factor_ref         0.1163
_reflns_number_gt                1849
_reflns_number_total             2964
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            eg3145sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     -P2yn
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2019385
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_symmetry_multiplicity
O O1 0.95990(19) 0.88009(9) 0.72219(12) 0.0311(4) Uani d . 1 1
F F1 1.28188(17) 0.62221(8) 0.75771(10) 0.0408(3) Uani d . 1 1
F F2 0.96248(16) 0.68269(8) 0.37687(10) 0.0375(3) Uani d . 1 1
F F3 0.62824(16) 1.05282(7) 0.35881(10) 0.0320(3) Uani d . 1 1
F F4 0.71941(17) 1.15006(8) 0.73743(10) 0.0416(4) Uani d . 1 1
C C1 1.2344(3) 0.60131(13) 0.64476(17) 0.0279(5) Uani d . 1 1
C C2 1.3041(3) 0.52711(14) 0.6123(2) 0.0326(5) Uani d . 1 1
H H2 1.3821 0.4909 0.6670 0.039 Uiso calc R 1 1
C C3 1.2570(3) 0.50662(14) 0.4971(2) 0.0326(5) Uani d . 1 1
H H3 1.3043 0.4557 0.4724 0.039 Uiso calc R 1 1
C C4 1.1418(3) 0.55928(13) 0.41686(19) 0.0298(5) Uani d . 1 1
H H4 1.1093 0.5451 0.3379 0.036 Uiso calc R 1 1
C C5 1.0764(3) 0.63254(13) 0.45580(18) 0.0262(5) Uani d . 1 1
C C6 1.1190(2) 0.65834(13) 0.56930(16) 0.0226(4) Uani d . 1 1
C C7 1.0584(2) 0.73719(12) 0.61288(17) 0.0237(4) Uani d . 1 1
H H7 1.0936 0.7435 0.6937 0.028 Uiso calc R 1 1
C C8 0.9598(2) 0.80204(12) 0.55473(17) 0.0227(4) Uani d . 1 1
H H8 0.9172 0.7994 0.4738 0.027 Uiso calc R 1 1
C C9 0.9178(2) 0.87745(12) 0.61683(17) 0.0226(4) Uani d . 1 1
C C10 0.8211(2) 0.94938(12) 0.54759(17) 0.0230(4) Uani d . 1 1
H H10 0.7903 0.9465 0.4665 0.028 Uiso calc R 1 1
C C11 0.7772(2) 1.01847(12) 0.59975(17) 0.0226(4) Uani d . 1 1
H H11 0.8147 1.0170 0.6809 0.027 Uiso calc R 1 1
C C12 0.6802(2) 1.09605(12) 0.55061(16) 0.0218(4) Uani d . 1 1
C C13 0.6070(2) 1.11323(13) 0.43514(16) 0.0229(4) Uani d . 1 1
C C14 0.5135(3) 1.18678(13) 0.39291(17) 0.0259(5) Uani d . 1 1
H H14 0.4659 1.1949 0.3129 0.031 Uiso calc R 1 1
C C15 0.4906(3) 1.24870(13) 0.46984(18) 0.0275(5) Uani d . 1 1
H H15 0.4261 1.2999 0.4423 0.033 Uiso calc R 1 1
C C16 0.5603(3) 1.23702(13) 0.58599(18) 0.0297(5) Uani d . 1 1
H H16 0.5456 1.2797 0.6389 0.036 Uiso calc R 1 1
C C17 0.6515(3) 1.16191(13) 0.62293(17) 0.0267(5) Uani d . 1 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
F1 C1 C2 118.09(18)
F1 C1 C6 117.34(18)
C2 C1 C6 124.6(2)
C1 C2 C3 117.9(2)
C1 C2 H2 121.1
C3 C2 H2 121.1
C2 C3 C4 121.2(2)
C2 C3 H3 119.4
C4 C3 H3 119.4
C5 C4 C3 117.7(2)
C5 C4 H4 121.1
C3 C4 H4 121.1
F2 C5 C4 117.09(18)
F2 C5 C6 118.20(17)
C4 C5 C6 124.71(19)
C5 C6 C1 113.95(18)
C5 C6 C7 126.13(18)
C1 C6 C7 119.91(18)
C8 C7 C6 129.02(19)
C8 C7 H7 115.5
C6 C7 H7 115.5
C7 C8 C9 119.84(18)
C7 C8 H8 120.1
C9 C8 H8 120.1
O1 C9 C8 121.46(18)
O1 C9 C10 121.30(18)
C8 C9 C10 117.24(17)
C11 C10 C9 119.53(18)
C11 C10 H10 120.2
C9 C10 H10 120.2
C10 C11 C12 129.61(19)
C10 C11 H11 115.2
C12 C11 H11 115.2
C13 C12 C17 113.64(17)
C13 C12 C11 126.63(18)
C17 C12 C11 119.72(18)
F3 C13 C14 117.79(17)
F3 C13 C12 117.66(17)
C14 C13 C12 124.55(18)
C13 C14 C15 118.33(19)
C13 C14 H14 120.8
C15 C14 H14 120.8
C16 C15 C14 120.82(19)
C16 C15 H15 119.6
C14 C15 H15 119.6
C17 C16 C15 118.10(19)
C17 C16 H16 121.0
C15 C16 H16 121.0
F4 C17 C16 118.19(18)
F4 C17 C12 117.25(18)
C16 C17 C12 124.56(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C9 1.233(2)
F1 C1 1.361(2)
F2 C5 1.355(2)
F3 C13 1.359(2)
F4 C17 1.360(2)
C1 C2 1.370(3)
C1 C6 1.404(3)
C2 C3 1.385(3)
C2 H2 0.9500
C3 C4 1.391(3)
C3 H3 0.9500
C4 C5 1.375(3)
C4 H4 0.9500
C5 C6 1.388(3)
C6 C7 1.458(3)
C7 C8 1.342(3)
C7 H7 0.9500
C8 C9 1.475(3)
C8 H8 0.9500
C9 C10 1.477(3)
C10 C11 1.334(3)
C10 H10 0.9500
C11 C12 1.460(3)
C11 H11 0.9500
C12 C13 1.390(3)
C12 C17 1.403(3)
C13 C14 1.375(3)
C14 C15 1.384(3)
C14 H14 0.9500
C15 C16 1.380(3)
C15 H15 0.9500
C16 C17 1.374(3)
C16 H16 0.9500
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
C2 H2 O1 2_746 0.95 2.32 3.256(3) 168.3
C16 H16 O1 2_656 0.95 2.31 3.255(3) 174.2
C4 H4 F3 2_645 0.95 2.58 3.429(2) 148.7
C14 H14 F2 2_655 0.95 2.49 3.314(2) 144.5
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
F1 C1 C2 C3 -179.28(18)
C6 C1 C2 C3 -0.3(3)
C1 C2 C3 C4 -0.4(3)
C2 C3 C4 C5 0.2(3)
C3 C4 C5 F2 -179.23(17)
C3 C4 C5 C6 0.9(3)
F2 C5 C6 C1 178.63(17)
C4 C5 C6 C1 -1.5(3)
F2 C5 C6 C7 -2.6(3)
C4 C5 C6 C7 177.34(18)
F1 C1 C6 C5 -179.83(17)
C2 C1 C6 C5 1.1(3)
F1 C1 C6 C7 1.3(3)
C2 C1 C6 C7 -177.72(18)
C5 C6 C7 C8 -3.8(3)
C1 C6 C7 C8 174.96(19)
C6 C7 C8 C9 -178.40(17)
C7 C8 C9 O1 -5.2(3)
C7 C8 C9 C10 175.51(17)
O1 C9 C10 C11 -0.4(3)
C8 C9 C10 C11 178.90(16)
C9 C10 C11 C12 -178.86(17)
C10 C11 C12 C13 1.9(3)
C10 C11 C12 C17 -179.01(18)
C17 C12 C13 F3 -179.93(15)
C11 C12 C13 F3 -0.7(3)
C17 C12 C13 C14 -0.5(3)
C11 C12 C13 C14 178.73(18)
F3 C13 C14 C15 179.83(16)
C12 C13 C14 C15 0.4(3)
C13 C14 C15 C16 0.2(3)
C14 C15 C16 C17 -0.6(3)
C15 C16 C17 F4 -179.64(17)
C15 C16 C17 C12 0.4(3)
C13 C12 C17 F4 -179.88(16)
C11 C12 C17 F4 0.9(3)
C13 C12 C17 C16 0.0(3)
C11 C12 C17 C16 -179.20(18)
