#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/34/2223482.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_2223482
loop_
_publ_author_name
'Zeng, Wu-Lan'
'Jian, Fang-Fang'
_publ_section_title
;
 5-(2-Fluorobenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione
;
_journal_coeditor_code           LH2910
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2587
_journal_paper_doi               10.1107/S1600536809038811
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C13 H11 F O4'
_chemical_formula_moiety         'C13 H11 F O4'
_chemical_formula_sum            'C13 H11 F O4'
_chemical_formula_weight         250.22
_chemical_name_systematic
;
5-(2-Fluorobenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione
;
_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                104.66(3)
_cell_angle_beta                 97.00(3)
_cell_angle_gamma                98.50(3)
_cell_formula_units_Z            2
_cell_length_a                   5.9907(12)
_cell_length_b                   7.6135(15)
_cell_length_c                   13.712(3)
_cell_measurement_reflns_used    2680
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      3.11
_cell_volume                     590.1(2)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_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      293(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       'φ and ω'
_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  0.0152
_diffrn_reflns_av_sigmaI/netI    0.0162
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5846
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         3.11
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             260
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.207
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2680
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0402
_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)+(0.0689P)²+0.0762P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1142
_refine_ls_wR_factor_ref         0.1222
_reflns_number_gt                2232
_reflns_number_total             2680
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh2910.cif
_cod_data_source_block           I
_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        590.0(2)
_cod_database_code               2223482
_cod_database_fobs_code          2223482
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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O4 0.24998(15) 0.52398(12) 0.08949(6) 0.0433(2) Uani d . 1 . .
F F -0.21328(14) 0.74829(12) 0.22191(7) 0.0610(3) Uani d . 1 . .
O O3 0.42130(16) 0.39182(13) 0.21066(7) 0.0487(2) Uani d . 1 . .
O O2 0.19470(18) 0.81052(13) 0.13437(7) 0.0532(3) Uani d . 1 . .
C C10 0.22839(19) 0.67636(17) 0.16038(9) 0.0387(3) Uani d . 1 . .
O O1 0.5140(2) 0.54637(16) 0.37345(8) 0.0694(4) Uani d . 1 . .
C C4 0.0848(2) 0.93620(17) 0.35028(9) 0.0418(3) Uani d . 1 . .
C C11 0.2576(2) 0.35465(17) 0.11792(9) 0.0413(3) Uani d . 1 . .
C C7 0.2194(2) 0.78997(18) 0.34775(9) 0.0436(3) Uani d . 1 . .
H H7A 0.2780 0.7790 0.4115 0.052 Uiso calc R 1 . .
C C9 0.2713(2) 0.66953(16) 0.26804(9) 0.0390(3) Uani d . 1 . .
C C6 -0.2546(2) 1.0510(2) 0.29876(11) 0.0521(3) Uani d . 1 . .
H H6A -0.3967 1.0306 0.2578 0.063 Uiso calc R 1 . .
C C5 -0.1258(2) 0.91420(18) 0.29004(9) 0.0430(3) Uani d . 1 . .
C C8 0.4099(2) 0.53311(18) 0.29079(10) 0.0455(3) Uani d . 1 . .
C C3 0.1648(3) 1.1072(2) 0.42261(11) 0.0547(4) Uani d . 1 . .
H H3A 0.3034 1.1261 0.4660 0.066 Uiso calc R 1 . .
C C13 0.3522(3) 0.2316(2) 0.03544(11) 0.0592(4) Uani d . 1 . .
H H13A 0.5007 0.2923 0.0301 0.089 Uiso calc R 1 . .
H H13B 0.2516 0.2058 -0.0286 0.089 Uiso calc R 1 . .
H H13C 0.3649 0.1179 0.0520 0.089 Uiso calc R 1 . .
C C2 0.0417(3) 1.2483(2) 0.43080(12) 0.0613(4) Uani d . 1 . .
H H2A 0.1004 1.3627 0.4775 0.074 Uiso calc R 1 . .
C C1 -0.1683(3) 1.2195(2) 0.36964(12) 0.0582(4) Uani d . 1 . .
H H1A -0.2522 1.3141 0.3762 0.070 Uiso calc R 1 . .
C C12 0.0242(3) 0.2714(2) 0.13214(12) 0.0566(4) Uani d . 1 . .
H H12A -0.0266 0.3564 0.1856 0.085 Uiso calc R 1 . .
H H12B 0.0317 0.1583 0.1503 0.085 Uiso calc R 1 . .
H H12C -0.0815 0.2462 0.0696 0.085 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 0.0033 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C10 O4 C11 . . 119.32(9) ?
C8 O3 C11 . . 118.75(9) ?
O2 C10 O4 . . 119.30(11) ?
O2 C10 C9 . . 124.62(11) ?
O4 C10 C9 . . 115.80(10) ?
C5 C4 C3 . . 116.79(12) ?
C5 C4 C7 . . 124.51(12) ?
C3 C4 C7 . . 118.56(12) ?
O4 C11 O3 . . 109.41(10) ?
O4 C11 C13 . . 106.34(11) ?
O3 C11 C13 . . 106.18(11) ?
O4 C11 C12 . . 110.47(11) ?
O3 C11 C12 . . 110.71(11) ?
C13 C11 C12 . . 113.52(12) ?
C9 C7 C4 . . 130.10(11) ?
C9 C7 H7A . . 114.9 ?
C4 C7 H7A . . 114.9 ?
C7 C9 C10 . . 125.14(11) ?
C7 C9 C8 . . 117.26(11) ?
C10 C9 C8 . . 117.09(10) ?
C5 C6 C1 . . 118.59(13) ?
C5 C6 H6A . . 120.7 ?
C1 C6 H6A . . 120.7 ?
F C5 C6 . . 118.32(12) ?
F C5 C4 . . 118.57(12) ?
C6 C5 C4 . . 123.07(13) ?
O1 C8 O3 . . 119.85(12) ?
O1 C8 C9 . . 124.13(12) ?
O3 C8 C9 . . 115.98(11) ?
C2 C3 C4 . . 121.18(14) ?
C2 C3 H3A . . 119.4 ?
C4 C3 H3A . . 119.4 ?
C11 C13 H13A . . 109.5 ?
C11 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C11 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C1 C2 C3 . . 119.93(14) ?
C1 C2 H2A . . 120.0 ?
C3 C2 H2A . . 120.0 ?
C2 C1 C6 . . 120.39(13) ?
C2 C1 H1A . . 119.8 ?
C6 C1 H1A . . 119.8 ?
C11 C12 H12A . . 109.5 ?
C11 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C11 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 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 C10 . 1.3460(15) ?
O4 C11 . 1.4434(15) ?
F C5 . 1.3529(16) ?
O3 C8 . 1.3457(16) ?
O3 C11 . 1.4460(15) ?
O2 C10 . 1.1996(15) ?
C10 C9 . 1.4826(16) ?
O1 C8 . 1.1979(16) ?
C4 C5 . 1.3843(18) ?
C4 C3 . 1.3978(19) ?
C4 C7 . 1.4639(17) ?
C11 C13 . 1.5018(18) ?
C11 C12 . 1.5041(19) ?
C7 C9 . 1.3385(17) ?
C7 H7A . 0.9300 ?
C9 C8 . 1.4904(17) ?
C6 C5 . 1.3753(19) ?
C6 C1 . 1.381(2) ?
C6 H6A . 0.9300 ?
C3 C2 . 1.380(2) ?
C3 H3A . 0.9300 ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 0.9600 ?
C2 C1 . 1.379(2) ?
C2 H2A . 0.9300 ?
C1 H1A . 0.9300 ?
C12 H12A . 0.9600 ?
C12 H12B . 0.9600 ?
C12 H12C . 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
_geom_hbond_publ_flag
C1 H1A O1 1_465 0.93 2.42 3.343(4) 174 yes
C7 H7A O1 . 0.93 2.42 2.798(2) 104 no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 325839
